TW201233734A - Diketopyrrolopyrrole pigment composition for color filter, coloring composition for color filter, and color filter - Google Patents

Abstract

This invention provides a diketopyrrolopyrrole pigment represented by formula (1), and a diketopyrrolopyrrolic pigment composition containing a diketopyrrolopyrrole pigment represented by formula (A-2) for color filter, wherein the diketopyrrolopyrrole pigmkent represented by formula (A-2) is contained in the composition in the amount of 1% mass to 15% mass with respect to a total amout mass of the diketopyrrolopyrrolic pigment.

Description

201233734 VI. Description of the Invention: [Technical Field] The present invention relates to a color filter quinonedipyrrolopyrrole pigment composition, a coloring composition for a color filter, and the use of the color filter A color filter formed by coloring the composition. [Prior Art] The liquid crystal display device controls the display of the light passing through the second sheet of the polarizing plate by controlling the degree of polarization of the light passing through the first polarizing plate by sandwiching the liquid crystal layer of the two polarizing plates. The device is mainly in the form of using a twisted nematic (TN) type liquid crystal. Since the color filter is provided between the two polarizing plates, the color filter can be used for color display. In recent years, it can be used for a television or a personal computer screen, so that the color filter has high brightness, high contrast, and high color reproducibility. Request for improvement. The color filter is attached to a surface of a transparent substrate such as glass to arrange two or more thin-colored filter segments of a different color hue in parallel or in a crosswise manner, or to fix the fine filter segments. The vertical and horizontal arrangement of the configurator. It is generally formed of filter segments of three colors of red, green, and blue, and the segments are, for example, finely several micrometers to several hundreds of micrometers, and each of the hues is arranged neatly in a specific arrangement. Generally, in a color liquid crystal display device, a transparent electrode for driving a liquid crystal is formed by vapor deposition or sputtering on a color filter, and further, an alignment film for aligning the liquid crystal in a certain direction is formed thereon. In order to sufficiently obtain the properties of the transparent electrode and the alignment film, in the production step of forming the color filter, the temperature is generally 203842 4 201233734, which is generally higher than 200 ° C, preferably 230 ° C or higher. Therefore, the current method for producing a color filter is a coloring agent which is excellent in light resistance and heat resistance, and the method of the pigment dispersion method is the mainstream. In the pigment dispersion method, the red filter segment is generally excellent in light resistance and heat resistance as a coloring agent and a pigment, a brewing pigment, an anthocyanin pigment, or a diazo pigment. The pigments are used singly or in combination. Among the diketopyrrolopyrrole pigments, c.i. Pigment Red 254 is a pigment which is particularly excellent in brightness, and therefore it is desired to further increase the brightness. Further, in recent years, there has been a strong demand for high contrast of color filters. Therefore, it is desirable to make the primary particle diameter of the monoketopyrrolopyrrole pigment as fine as possible. However, since the micronized diketopyrrolopyrrole pigment has a property of being easily crystallized by its intermolecular hydrogen bond, it causes crystallization in the heating step in forming a color filter, and is produced. The problem of foreign bodies. Further, the diketopyrrolopyrrole pigment can be obtained by the production method disclosed in Patent Document i φ and Patent Document 2 (hereinafter referred to as "succinate synthesis method"). Patent Document 3 discloses a method of obtaining a mixture of at least two diketone groups having different structural diketone ratios in a succinate synthesis method using a plurality of nitrile compounds as a raw material. Patent Document 4 describes a mixture of at least two diketo-pyrrolopyrrole pigments having different structures obtained by a succinate synthesis method using a nitrile compound having a plurality of specific structural formulas as a raw material. For color filters. 323842 5 201233734 discloses a coloring composition for a color filter by using a diketopyrrolopyrrole pigment (mainly CI Pigment Red 254), at least one specific structure, in Patent Document 5 and Patent Document 6. The bisaryldiketopyrrolopyrrole compound and the pigment derivative are used in combination to provide high contrast and suppress crystallization due to the heating step.

Patent Document 7 discloses a coloring composition for a color filter using a brominated diketopyrrolopyrrole pigment. Further, Patent Document 8 describes the use of a brominated diketopyrrolopyrrole pigment composition for a color calendering sheet. [PRIOR ART DOCUMENT] [Patent Document] Patent Document 1 Patent Document 2 Patent Document 3 Patent Document 4 Japanese Laid-Open Patent Publication No. SHO-58-210084 Bulletin 2007-514798

Patent Document 5 WO 2009/081930, PCT Patent Application Publication No. JP-A-2009- 149 074, JP-A-1999- 231 516, JP-A-1999-231516, JP-A-2009-144115 A problem is to provide a diketopyrrolopyrrole pigment composition for a color filter, a coloring composition for a color filter, and a color filter using the same, and the color filter uses a diketopyrrole The pyrrole pigment composition has good brightness and contrast, and it is not easy to cause crystal precipitation of the di-p-pyrrolopyrrole pigment even by the thermal step of adding 323842 6 201233734. According to a first embodiment of the present invention, a color filter-based pyrrolopyrrole pigment composition comprising a di-n-propylpyrrolopyrrole pigment represented by formula (1) and a formula (A-2) A diketopyrrolopyrrole pigment composition for a color filter of a diketopyrrolopyrrole pigment, wherein the content of the diketopyrrolopyrrole pigment represented by the formula (A-2) is a dimercaptopurine The total mass of the pyrrole-based pigments is based on i mass% to 15% by weight.

Br

^ (1) Formula (Α-2) Φ [In the formula (Α-2), Α and Β are independently a hydrogen atom, a fluorine atom, an iodine atom, a cyano group, an alkyl group having a carbon number of i to 12, and may have a substitution. Phenyl group, -cf3, -or1, _SR2, -N(R3)R4, -C00R5, -C0NH2, -C0NHR6, -C0N(R7)R8, -s〇2NH2, -S〇2NHR9, or -S( M(R1D)R", R1 to R11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent; however, A and B are not simultaneously a hydrogen atom. Further, the first embodiment relates to a diketone group of the above-mentioned color calendering sheet 0 to 323842 7 201233734, a pyrrole pyrrole-based pigment composition, wherein the diterpene ratio of the above formula (A_2) is more than The pigment is any one of the formula (A-2-1), the formula (A-2-2), and the formula (A-2-3) sulfhydryl group (A-2-4);

[In the formula (A-2-3) and the formula (A-2-4), or a phenyl group which may have a substituent R6 to R8 each independently a carbon group of 1 to 12]. In addition, the first embodiment relates to a dimercapto fluorenylpyrrole pigment composition for a color calendering sheet, which further contains c. Pigment Red 254 as a diketopyrrolopyrrole pigment. In addition, in the first embodiment, the diketone group represented by the formula (1) is used as a reference for the total mass of the dimercapto pyrene (tetra) pigment composition for the color calender sheet And the total content of the 323842 8 201233734 material and the CI pigment red 254 is 85% by mass to 99% by mass. In addition, the first embodiment relates to a diketopyrrolopyrrole pigment composition for a color filter, wherein the quality of the dimethypyrrolopyrrole pigment and CI Pigment Red 254 represented by the formula (1) The ratio is 20: 80 to 99: 1. Further, the first embodiment relates to a diketopypyrrole ratio σ pigment composition of the above-mentioned color filter, which further contains a dye derivative. Further, the second embodiment relates to a diketopipyrrolopyrrole pigment composition for a color filter, which comprises a diketopoxime represented by the formula (1) and a pigment of 0 to 11 and a formula ( The two bases η shown in Β-2) are more than 嘻. The color filter of the pigments is a diketopyrrolopyrrole pigment composition, wherein the mass ratio of the formula (1) to the formula (Β-2) is 97:3 to 85:15;

Br

Formula (1) Formula (B-2) [In the formula (B-2), A and B are each independently a hydrogen atom, a fluorine atom, a gas atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, and Phenyl group having a substituent, _CF3...〇Rl -SR2 > -N(R3)R4 ^ -C〇〇R5 , -c〇nh2 v -CONHR6 ^ -CGN(R7)R8 > -SO2NH2, -SO2NHR9, Or -SC^j^R1. ), ^11, R1 to R11 are each independently a thiol having a carbon number of i to 12, a phenyl 323842 9 201233734 phenyl group or a aryl group which may have a substituent; but A and B are not simultaneously hydrogen atom]. In the second embodiment, the diketoppyrrolopyrrole pigment composition for a color filter, wherein the formula (β_2) is a formula (6_2_丨), a formula (B-2-2), Any one of the formula (B-2-3), the formula (B-2-4), the formula (B-2-5), the formula (B-2-6) or the formula (B-2-7);

Br

Formula (B-2-1> ^ (B-2-2) Formula (B — 2 — 3) ίζ (Β - 2 -4)

[In the formula (Β-2-4), the formula (Β-2-6), and the formula (Β-2-7), R to R are each independently a carbon group having 1 to 12 carbon atoms, or may have a substituent. Phenyl]. Further, the second embodiment relates to a diketone-pyrometric quinone pigment composition for a color filter, which further contains a pigment derivative 323842 10 201233734. In addition, the third embodiment relates to a coloring composition for a color filter, which comprises a coloring agent, a binder resin, and a coloring composition of an organic solvent, wherein the coloring agent contains the diketopyrrole of the first embodiment. Pyrrole pigment composition. In the third embodiment, the coloring composition for a color filter further contains a photopolymerizable monomer and/or a photopolymerization initiator. In addition, the fourth embodiment relates to a colored composition for a color filter, which comprises a coloring agent, a binder resin, and a coloring composition of an organic solvent, wherein the coloring agent contains the diketone group of the second embodiment. ° P-pyrazine p-series pigment composition. In the fourth embodiment, the coloring composition for a color filter further contains a photopolymerizable monomer and/or a photopolymerization initiator. According to a fifth aspect of the present invention, there is provided a coloring composition for a color filter comprising a pigment (A), a binder resin (CB), and a coloring composition for a color φ color filter of a solvent, wherein the pigment (A) is a pigment (A1) represented by the formula (1), and the binder resin (CB) is an alkali-soluble photosensitive resin (C-B1). 323842 11 201233734

Further, the fifth embodiment relates to the above-mentioned color filter for a color filter, wherein the pigment (A) further contains at least one of a diketopyrrolopyrrole pigment other than the color grade, and an azo pigment/lean 4 (A1) material, anthraquinone pigment, quinacridone pigment #benz imi dazo 1 one pigment, and quinoline pigment were selected as the imidazole. In a further embodiment, the fifth embodiment relates to the above-mentioned color data, wherein the method further comprises a second compound, a phosphine compound, an azole compound, and a grade compound. Photopolymerization initiator (CD). At least the sixth embodiment of the present invention relates to a composition, a coloring composition for a color-tone calender sheet containing a pigment (A) or a binder resin, wherein the pigment (A) is a color containing the formula 2 The pigment (8)' is bonded to contain a resin (D-B1) having a composition of = to (D-b3). Bl) 323842 12 201233734

Br

(1) (D-bl) has a structural unit of a carboxyl group: 2 to 60% by weight (D-b2) a constituent unit having an aromatic ring group represented by the formula (D-2) or (D-3): 2 Component unit having an aliphatic ring group represented by formula (D-4) or (D-5) up to 80 mass%/〇(D-b3): 2 to 60 mass%/〇

Formula (D-2)

Formula (D-3)

R

[In the formula (D-2) and the formula (D-3), R is a hydrogen atom or an alkyl group having a benzene ring having 1 to 20 carbon atoms; and the dotted line in the formula (D-3) means a phase a benzene ring adjacent to a benzene ring and containing one or more saturated or unsaturated heterocyclic rings which may have a substituent 323842 13 201233734

In the coloring composition for a color filter, the pigment (Α) further contains at least one of a diketopyrrolopyrrole pigment other than the pigment (Α1), and an azo pigment. Among the groups of Huijing pigments, lanthanide pigments, quinophthalone pigments, benzimidazolone pigments, and quinoline pigments. In addition, the coloring composition for a color filter further contains at least one selected from the group consisting of an acetaminophen compound, a phosphine compound, an imidazole compound, and an oxime ester compound. The above photopolymerization initiator (DD). According to a seventh aspect of the invention, there is provided a color filter comprising a filter segment formed of the coloring composition for a color filter. The Japanese Patent Application No. 2011-76928, which was filed on January 28, 2011, and the Japanese Patent Application No. 323842, which was filed on March 31, 2011, was filed on January 31, 2011. The subject matter described in Japanese Patent Application No. 2011-271836, filed on Jan. 13, 2011, the entire disclosure of which is hereby incorporated by reference. [Embodiment] Hereinafter, embodiments of the present invention will be described in detail.

In addition, the following "c·L" means a color index (C·丨.). When it is expressed as "(meth) acrylate", "(meth) acrylate" or "(meth) acrylamide", unless otherwise stated, it means "acrylate" and / or methacrylate "Acrylic and/or mercapto-butanoic acid", "acrylamide" and/or methyl propyl amide. [Di-pyrrolopyrrole pigment composition] First, a diketopyrrolopyrrole pigment composition according to an embodiment of the present invention will be described. [First Embodiment] (di-p-pyrrolopyrrole pigment composition) The first embodiment is a diketone-based microparticle pigment composition for a color calendering sheet, which is represented by the following formula (1). The two ketone scales are combined with the ketones and the specific heterodiketones of the following formula (A-2). The content of the filament H shown in the above formula (A-2) is called the content of the scale (four), and the total mass of the pigments of the base and the base of each of the bases is 15% by mass. ~Berry 323842 201233734 Brightness is improved by applying a brominated diketone to a specific pigment (formula (1)) for a color filter. Further, it has been found that a diketopyrrolopyrrole pigment (formula (A-2) (hereinafter referred to as "specific heterodiketopyrrolopyrrole pigment A") having a substituent introduced in a specific structure is used. The ketopyrrolopyrazine pigment composition can obtain a color filter which not only has high brightness but also high contrast and can suppress crystal precipitation due to the heating step. The specific heterodiketopyrrolopyrrole selected here. Pigment A, because of the small interaction with the resin component, can effectively cover the active surface of the brominated diketopyrrolopyrrole pigment, and can inhibit the thermal agglomeration of the pigment caused by the heating step, so that a small amount can be contained. The high-contrast and crystallization-preventing effect are exhibited. Further, the specific heterodiketone oxime 11 is more excellent in D color than the pigmentation inhibitors of the pigments A, and the amount of addition can be reduced. Non-destructive brominated diketone-based "excellent brightness enhancement effect of pyrrole-pyrrole pigment. Further, the diketopyrrolopyrrole pigment composition contains a specific heterodiketopyrrolopyrrole pigment A Therefore, the viscosity stability is excellent. φ According to the first embodiment, a diketopyrrolopyrrole pigment composition for a color filter can be provided, which has good brightness and contrast, and does not cause a diketone group even by a heating step. The crystal of the pyrrolopyrrole pigment precipitates, and further, the viscosity stability is excellent. 323842 16 201233734

[In the formula (A-2), A and B are each independently a hydrogen atom, a fluorine atom, an iodine atom, a cyano group, an alkyl group having a carbon number i to 12, a phenyl group which may have a substituent, -CF3, -Of , -SR2, -N(R3)R4, -C00R5, -C0NH2, -C0NHR6, -C0N(R7)R8, -S〇2NH2, -S〇2NHR9, or -SiMCR^R11, R1 to R11 are each independently carbon An alkyl group of 1 to 12, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent; but A and B are not simultaneously a hydrogen atom]. The above-mentioned carbon number of 1 to 12 may be a straight bond or a branched form, and specifically, for example, an anthracene group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a second butyl group, or a Tributyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, 1,5-dimethylhexyl, 1,6-dimethylheptyl, 2-ethylhexyl, etc., but It is not limited to this. The phenyl group which may have the above substituent may, for example, have an alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, an amine fluorenyl group, an amine sulfonyl group, and a carbon number of 1 to A phenyl group of a substituent such as an alkoxy group. The phenyl group may have one or two or more such substituents. More specifically, for example, phenyl, p-nonylphenyl, 4-second butylphenyl, p-nitrophenyl, p-methoxy 323842 17 201233734 phenyl, p-chlorophenyl, 2, 4-di The chlorophenyl group and the glycerin group are not limited to these. The above-mentioned aromatic silk system which may have a substituent. For example, a substituent having a carbon number of 1 to 4, a pyridyl group, an amine group, a number of cores, and a substituent may be mentioned. Aromatic base. ^Base system may have i or more than one of these, such as stupid methyl, 4-methylbenzyl, ^ body preparation A Noda Gan 4 Le-butyl thiol, 4-M basic A The group, 4 fluorene methyl group, 2, 4_ are limited to these. T-sign, but not effective, by the formula (A-1 = '9 from the contrast and crystallization * inhibition 2-3), the formula (^ heart ^ to the alkyl group on 8, or can have a substitution The number of 妷, 妷 4 Λ Λ Λ t t t t t t t t 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The steric hindrance effect caused by the substituents of the phenyl group and the phenyl group and the third group can suppress the bulkiness of the ruthenium group and have a carbamide group (amine sulfhydryl group) and a phenyl group. Characteristics of each pigment 二 two: fixed heterobasic scales and secrets (four) k❹ 4 consumption two Ming 323842 201233734

[In the formula (A-2-3) and the formula (A-2-4), R6 to R8 each independently represent an alkyl group having 1 to 12 carbon atoms or a phenyl group which may have a substituent ^]. Specific examples of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) are exemplified below, but are not limited thereto. 323842 19 201233734

323842 20 201233734

323842 21 201233734

323842 22 201233734

Cl

Cl

Formula (A-2 - 1 5)

Formula (A - 2 _ 1 6)

Cl

Formula (A-2 - 1 7)

Cl

The pigment composition of the formula (A-2 - 18) is characterized in that the content of the specific heterodiketone represented by the formula (A_2) is slightly different from that of the squamous pigment A, and the age of the squama pigment is 5 (four). Preferably, the range of the quality of the branches is H). If the specific hetero-network of the formula (A_2) 323 323842 23 201233734 p is proportional to each other. When the ratio of the pigments A exceeds 5% by mass, the crystal precipitation suppressing effect can be obtained, but the brightness of each of the pigments of the filled diketone-α and the saponin of the formula (1) is deteriorated. On the other hand, when the ratio of the specific heterodikeke group of the formula (Α·~2) is less than 1% by mass, the effect of high contrast and inhibition of crystal precipitation is not sufficient. When the effect of suppressing the crystallization precipitation is insufficient, light scattering occurs due to precipitation of crystal foreign matter on the surface of the coating film in the heating step, resulting in a decrease in brightness and contrast ratio. Therefore, by using a diketopyrrolopyrrole pigment composition containing a specific heterodiketopyrrolopyrrole pigment A in the above ratio, high shelliness and high contrast can be achieved, even by a heating step. Crystallization of the diketopyrroloindole/argon pigment. Further excellent viscosity stability can be obtained. In the range in which the effect is not impaired, the pigment composition may be used in combination with a diketopyrrolopyrrole pigment of the formula (1) and a specific heterodiketopyrrolo 11 of the formula (A-2). The base π is slightly smaller than the beta pigment. Further, for example, C.I. Pigment Red 254, 255, 264, 272, C.I. Pigment Orange 71, and a diketopyrrolopyrrole pigment such as Ru 73 or 81 are not limited thereto. The diketone is used in combination with the pyrrole-based pigment, and C.I. Pigment Red 254 is #. The reason why CI Pigment Red 254 is better is to produce a specific heterodiketopyrrolopyrrole pigment of the formula (Α-2) by a succinic acid diacetate synthesis method, which is generally not suitable for the diketone group of the formula (1). The superior brightness of the bilo-β-pyrrol pigment affects. When the pigment composition contains CI Pigment Red 254, it is preferably a diketopyrrolopyrrole pigment represented by the formula (1) based on the total weight of the diketone π ratio and the icoric pigment (100% by mass). With CI Pigment Red 254 夕人^•丄人< σ计 containing 323842 24 201233734 The amount is 85% by mass to 99% by mass. When the total content of the diketone group and the CI pigment red 254 of the formula (1) is less than 85% by mass, the brightness enhancement effect may be less, and when it is more than 99% by mass, Since the specific heterodiketopyrrolopyrene has a smaller content than the azole pigment A, the contrast ratio and the crystal precipitation suppressing effect may not be sufficiently obtained. Further, the mass ratio of the diketone group π ratio of each of the pyrrole pigments represented by the formula (1) to the C.I. Pigment Red 254 is preferably from 20:80 to 99:1. Better system 50: 50 to 99: 1. In the total of the diketopyrrolopyrrole pigment represented by the formula (1) and the CI pigment red 254, the content of the diketoppyrrolopyrrole pigment represented by the formula (1) is 20% by mass or more, and the brightness enhancement effect is obtained. Large, so better. Further, a diketopyrrolopyrrole pigment of the formula (1) and a diketopyrrolopyrrole pigment other than the specific heterodiketopyrrolopyrrole pigment of the formula (Α-2) may also be used. A specific heterodiketopyrrolopyrrole pigment of the formula (B-2) described later. In this case, the mass ratio of the diketopyrrolopyrrole pigment of the formula (1) to the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2) is preferably from ^97:3 to 85:15. (Production method of diketopyrrolopyrrole pigment) The diketopyrrolopyrrole pigment represented by the formula (1) can be obtained by a known method described in the handbook of International Publication No. 2009/144115. Further, the diketopyrrolopyrrole pigment represented by the formula (1) can be produced by a succinic acid diester synthesis method. That is, the 4-bromobenzonitrile 2 mole is in an inert organic solvent such as a third pentanol, in the presence of an alkali metal or an alkali metal alkoxide, in an amount of 80 to 100 mol of the succinic acid diester. The condensation reaction is carried out at a high temperature of 110 ° C to form a metal salt of each compound having a diketone ratio of p and a ratio of π to 17. Following the 323842 25 201233734, the metal salt of the diketo-based oxime-compound compound is protonated by using water, alcohol, acid or the like to obtain a brominated diketopyrrolopyrrole pigment. At this time, the size of the obtained primary particle diameter can be controlled by the type, ratio or amount of protonation temperature, water, alcohol or acid. The method for producing the diketopyrrolopyrrole pigment represented by the formula (1) is not limited to this method. The specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) is carried out, for example, by the method described in Synth·C〇mmun_, 1988, 18, 1213 and Tetrahedr〇n, 58(2·)5547-ship. synthesis. The method for producing the (tetra) enthalpy Φ-based ratio and the specific pigment Α is not limited to this method. Further, the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) can also be synthesized as a mixture with C.I. Pigment Red 254. In the method of synthesizing acid diesters, it is possible to use a method using at least two structurally different carbonitrile compounds (hereinafter, referred to as "succinic acid diester co-synthesis method", which is based on W02009/ In the method described in the manual No. 081930, the plurality of benzonitrile compounds used are selected from the group consisting of 4_gasbenzonitrile and the abbreviated nitrile compound represented by the following formula (A_3) to give the formula (A-2). The specific heterodiketopyrrolopyrrole pigment A is produced as a mixture with αι. Pigment Red 254. Ν〇Ηάβ 8 Formula (Α-3) [In the formula (A-3), A and B are each independently hydrogen. Atom, fluorine atom, iodine atom, cyano group, alkyl group having a carbon number of 12, phenyl group which may have a substituent, _CF3, _〇R], _sr2, 323842 26 201233734 -N(R)R4, -COOR5, -CO·, -C0NHR6, _c〇N(R7)R8, _s〇2NH2, -S〇2NHR9, or -StMClOR11, = to Rn are each independently a C 1 to 12 alkyl group, a phenyl group which may have a substituent Or an aryl group which may have a substituent; but A and B are not simultaneously a hydrogen atom]. An alkyl group having an inverse number of 1 to 12, a phenyl group which may have a substituent, or may have a substituent The alkyl group is the same as the group in the above formula (A_2). The pigment composition may be a mixture of the two groups of the formula I (n), and the ratio of the pigments to the specific hetero-bases. The pigment Α is separately mixed by the manufacturer and used as a mixture of the specific hetero-dipyridylpyrrole pigment oxime synthesized by the succinic acid diester co-synthesis method, and the formula (1) is shown. The keto-pyrrolopyrrole pigment is used in combination, and is simply mixed before dispersing the pigment in the pigment carrier, or may be pulverized and mixed by a salt grinding treatment. In the pigment composition, the formula (1) Ketopyrrole. Specific pyridyl groups of the formula (Α~2). Compared with 嘻 and „ each pigment a, and c. I. Pigment red 254 mass ratio can use TOF- MASS, FD-MASS, LC-MASS or (10)R' is analyzed. Or, as disclosed in Japanese Laid-Open Patent Publication No. 08-199085, the composition of the diketopyrrolopyrrole pigment in tetrahydrofuran is combined with a third. Base dicarbonate and 4-dimethylaminopyridine are converted to the obtained soluble di-base each at room temperature After the compound, it can also be analyzed by NMR, MASS or LC-MASS, or the ratio of NH to ° can be compared with the hydrogen of the NH group, which is substituted with a functional alkyl group or the like to be converted into a soluble one. The above analysis is carried out after the diketopyrrolopyrrole. 323842 27 201233734 (Pigment Derivative) The pigment composition can be used for the purpose of suppressing the growth of the pigment crystal and improving the pigment dispersibility. The pigment derivative of the substance may, for example, be a diketopyrrolopyrrole derivative, a benzisoindole derivative, an anthracene derivative, a dioxane derivative, a thiazine indigo derivative, or an azo pigment derivative. , quinophthalone derivatives, quinocridine derivatives, and the like. The structure of the dye derivative is exemplified by the pigment derivative represented by the following formula (4), but is not limited thereto. P-Lm Formula (4) [In the formula (4), a P-based diketopyrrolopyrrole residue, a benzoisoindole residue, an anthracene derivative, a diterpene residue, a tidal indigo residue, an azo color residue a base, a quinacridone residue, a quinophthalone residue, and the like. m is an integer of 1 to 4, 隹L is independently -OH; -SCbH, -c〇〇H, a monovalent to trivalent metal salt or an alkylammonium salt of such an acidic group; may have a substituent a quinone imine methyl group; a group represented by the following formula (a), (b), (c), (d), (e), or (f), 323842 28 201233734

Rie •X~Y-(CH2)n^N; Formula (a) R1y_^R19 -XN N—R« R20, R21 Formula (b) R23 N=/ X A R2d Formula (丨~Z-〇~R2s (d) X is ~S〇2~ or direct bonding,

0-r2s -zO^nh Formula (e) Formula (f) -CO-' -CH2- ^ -CH2NHCOCH2-' -CH2NHS〇2CH5 Y is NH~, -〇-, -S-, or direct bonding, n An integer of 1 to i, R and R17 are each independently a hydrogen atom, a carbon group having 1 to 2 carbon atoms which may have a substituent, or an alkenyl group having 2 to 30 carbon atoms which may have a substituent, and R16 and R become The integral 'containing a nitrogen, oxygen, or sulfur atom as necessary to form a heterocyclic ring which may have a substituent.

Rl8 'R19, R2°, R21 and R22 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkenyl group having 2 to 20 carbon atoms which may have a substituent, and R is a formula (a) Or a substituent represented by the formula (b), R24 is a chlorine atom, -OH, an alkoxy group, a substituent represented by the formula (a) or the formula (b), and Z is -C0NH---NHC0---S 〇2NH-, or -NHS02-, R25 is a hydrogen atom, -NH2, -NHCOCH3, -NHR26 or a substituent represented by the formula (c), where R26 is a substituent having a carbon number of 1 to 20 Base ' 323842 29 201233734 A dilute group having a carbon number of 2 to 20 which may have a substituent. The metal of 1 to 3 is exemplified by sodium, potassium, town, turn, iron, or sulphur. Further, the alkylamine salt may, for example, be an ammonium salt of a long-chain monoalkylamine such as octylamine, laurylamine or stearylamine; or palmityl-trimethylammonium salt or dilauryldimethyl A 4-alkylammonium salt such as an ammonium salt or a distearyldimethylammonium salt. The substituent of the urethane imino group which may have a substituent, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a heterocyclic ring which may have a substituent, and may, for example, be a halogen atom or a nitro group. A cyano group, an amine sulfhydryl group, an N-substituted amine fluorenyl group, an amine fluorenyl group, an N-substituted amine, a chloro group, a decyloxy group having a carbon number of 1 to 2 Å, and a pyridyl group having 1 to 20 carbon atoms. Base, etc., but is not limited to this. The pigment derivative is a mercaptosulfide and sulfur which is dehydrated and condensed with N-hydroxydecyl imine by sulfuric acid in a sulfuric acid or fuming sulfuric acid. After the sulfonation of the gas, the gas is synthesized by a known method such as a sulfoximation reaction in which an amine component such as dimercaptopropylamine is reacted. _ The amine component used to form the substituent represented by the above formula (a), formula (b), and formula (c) may, for example, be didecylamine, diethylamine or mercaptoethylamine. , M,N-ethylisopropylamine, N,N-ethylpropylamine, N,N-methylbutylamine, N,N-methylisobutylamine, N,N-butyl Base amine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-second butylanamine, dibutylamine, di-tert-butylamine, Diisobutylamine, N,N-isobutyl-t-butylamine, dipentylamine, diisoamylamine, dihexylamine, dicyclohexylamine, di(2-ethylhexyl)amine, Dioctylamine, N,N-decyl octadecylamine, dimethylamine, diallylamine, N,N-ethyl-1,2-dimercaptopropylamine, N, N- 323842 30 201233734 Methylhexylamine, oleylamine, distearylamine, N,N-dimethylaminomethylamine, N,N-dimethylaminoethylamine, N, N-didecylaminopentylamine, N,N-dimethylaminobutylamine, N,N-diethylaminoethylamine, N,N-diethylaminopropylamine, N,N-diethylaminohexylamine, N,N-diethylaminobutylamine, N,N-diethylaminopentylamine, hydrazine, hydrazine-dipropylaminobutylamine, hydrazine, hydrazine-dibutylaminopropyl Amine, hydrazine, hydrazine-dibutylaminoethylamine, hydrazine, hydrazine-dibutylaminobutylamine, hydrazine, hydrazine-diisobutylaminopentylamine, hydrazine, hydrazine-methyl-lauric Aminopropylamine, hydrazine, hydrazine-ethyl-hexylaminoethylamine, hydrazine, hydrazine-distearate aminoethylamine, hydrazine, hydrazine-dioleylaminoethylamine, hydrazine , Ν-distearrylamidobutylamine, piperididine, 2-mercaptobite, 3-mercaptobite, 4-methylbendidine, 2,4-dimethyla Biting (2, 4-lupetidine), 2,6-diindenyl tour, 3, 5-dimercaptotrione bite, 3-p-sterol, methyl-bit acid, and isepipecotic acid ), Isopiperidic acid ester, Ethyl pipecolic acid ethyl ester, 2-piperidinyl alcohol, Pyrrolidine, 3-Phase ratio bite, N-Aminoethyl group bite, N-Dutamine Base ethyl-4-methylpiperidine, N-aminoethylmorpholine, N-aminopropyl piperidine, N-aminopropyl-2-methylpiperidine, N-butylpropyl- 4-mercaptopiperidine, N-aminopropylmorpholine, N-methylpiped, N-butylpiperidin, N-methylpiperidin, 1-cyclopentylpipenine, 1-amino-4-methylpiperidin, 1-cyclopentylpiped, etc., but not limited thereto . Further, when a substituent is introduced into the azo dye, the substituent is introduced into the diazo component or the couplant component in advance, and then the azo dye derivative is produced by a coupling reaction. The method of using the dye derivative can be exemplified by dispersing a diketopyrrolopyrrole 323842 31 201233734 material in a pigment surface and mixing it with water or an organic solvent at the time of manufacture of the fabric. The method or the method of adding the grind. The pigmented street organism is used in the production of pigments or in the method of organic spray mixing treatment or grinding treatment.

The method exhibits an effect of inhibiting the growth of diketone scales and scaly crystals. It is expected that the pigment derivative is effectively adsorbed on the surface of the diketopyrrolopyrrole pigment without being easily removed. Attached. Therefore, the structure of the pigment derivative is usually a chemical construct similar to the pigment used. For this reason, when a dimercaptopyrrolopyrrole pigment is produced, it is generally effective to have a diketopyrrolopyrrole structure, a thiomorphin blue structure, a benzisoindene structure, and a quinone structure. Further, when a dye derivative is used, it is desirable not to impair the color tone of the dipyrrolopyrrole pigment composition. From the point of view of hue, it is advisable to present a yellow, dially-dyed diketopyrrolopyrrole derivative, a stupid iso-pyridinium derivative, a snorkeling blue derivative, an azo dye derivative or an anthrone derivative. Use. 5至四〇质量份的范围圈。 The amount of the pigment derivative, the amount of the composition of the second layer of the composition of the mass fraction of 0.5 to 4 parts by mass. More preferably, it is in the range of 3 to 35 parts by mass based on the diketopyrrolopyrrole pigment composition. When the amount is less than 5% by mass, the growth inhibition effect of the spherulite may be insufficient, and when it is more than 4 parts by mass, the good color tone of each of the diketopyrrolopyrrole pigments is impaired. Specific examples of the dye derivative used in the diketopyrrolopyrrole pigment composition are described below, but are not limited thereto. 323842 32 201233734 (Specific Example of Diketopyrrolopyrrole Derivative) The diketopyrrolopyrrole derivative may specifically be a compound represented by the following formula (5) or (6), but is not limited thereto. .

Lm type (5)

Formula (5-1) L= -COOH m=2 Formula (5-2) L = -S03H m=2 Formula (5-3) L = -S02NH2 m=2 Formula (5-4) l = —S02NH( CH2)2N(C2H5)2 m=2 Formula (5-5) L= -S02NH(CH2>3N(CH3)2 m=2 Formula (5-6) L= -CH2NHCOCH2N(C4H9)2 m=2 Formula ( 5 - 7 ) L = -CH2NHCOCH2NH(CH2)2N(CH3)2 -m=2 Formula (5-8) L= -S02NH(CH2)3N(C2H5)2 m=2

0

02 /"""\ 式(5·10) L= -s -N N-C2H5 m=2 N/ 323842 33 201233734

Formula (6 -1 > Formula (6-2> Formula (6-3) Formula (6-4) Formula (6-5> Formula (6 - 6> Formula (6-7) Formula (6-8) Formula (6-9) Formula (6-10)

Formula (6) L = -SO3H m=2 L = one S02NH(CH2hN(C2Hsh L= -S〇2NH(CH2)3N(CH3)2 L= -CH2NHCOCH2N(C4H9)2 L= —CH2NHCOCH2NH(CH2)2N( CH3>2 0 II I rn=1 m=2 m=2 m—2 m=2

0 〇2 〇1 S -N N-C2H5 m=2 2 5 -S02NH{CH2)2N(CH3)2 m=2 Φ (Specific examples of benzindole derivatives) Benzoisoindole derivatives are specifically The compound represented by the following formula (7) is used, but is not limited thereto. 34 323842 201233734 Equation (7) Equation (7-1) L = —so2nhc3h6n(ch3)2 Equation (7-2) L = —S02NHC4H8N(CH3)2 Equation (7-3) L = —S02NHCH2N(CH3)2 (7-4) L = —so2nhc2h4n(c2h5>2 Equation (7-5) L = —so2nhc2h4n(ch3)2 Equation (7-6) L = —so2nh(ch2>2n(ch3)(c2h5) Equation (7 -7) L = a S02NH(CH2)2N(CH3)(n-C3H7) Formula (7-8) L = —S02NH(CH2)3N(C2H5)2 Formula (7-9) L = —S02NH(CH2>3N(C4H9>2 Formula (7-10) L = —S02NH(CH2)4N(C2H5)2 Formula (7-1 1) L = —S02NH(CH)(CH3)(CH2)N(CH3)2 Formula ( 7-12) L = ——so2nh(ch2)(ch)(ch3>n(ch3)2 Equation (7-1 3> L = —302ΝΗ((:Η2)2Ν(ί·(:3Η7)2 7-14) L = —S02NH(CH2hN(C2H5)2

(Specific Example of Anthracene Derivative) Specifically, the anthracene derivative may be a compound represented by the following formula (8), but is not limited thereto. 35 323842 201233734

Formula (8>

Formula (8-1> Formula (8-2) Formula (8-3) Formula (8:4) Formula (8-5) Formula (8-6) Formula (8-7) Formula (8-8 > Formula ( 8-9> L= -OH L= -COOH L= -S03H L=1 SO2NH2 L = -S02NH(CH2)2N(C2H5)2 L= -S02NH(CH2)3N(CH3)2 L= -CH2NHCOCH2N(C4H9 ) 2 L = -CH2NHCOCH2NH(CH2)2N(CH3>2 o Formula (8-1 0)

(Specific Example of Diterpene Derivative) The diterpene derivative may specifically be a compound represented by the following formula (9), but is not limited thereto.

36 323842 201233734

Formula (9)

Formula (9-1) L= -OH m=2 Formula (9-2) L= -COOH m=2 Formula (9-3) L= —S03H m=2 Formula (9-4) L = One SO2NH2 m =2 Formula (9-5) L = -S02NH(CH2)2N(C2H5)2 m=2 Formula (9-6) L= -S02NH(CH2)3N(CH3)2 m=2 Formula (9-7) l= -ch2nhcoch2n(c4h9)2 m=2 Formula (9-8> L = A CH2NHCOCH2NH(CH2)2N(CH3>2 Formula (9-9) L = -C2-N^lm=1 m=2 Formula ( 9-1 0) N-C2H5 m=2 (Specific example of the tidal indigo derivative) The compound represented by the following formula (10) can be specifically used as the thiazolidine derivative, but is not limited thereto. 201233734

Formula (10-1) L = -S02NH(CH2)3N(C2H5)2 m=2 Formula (10-2) l = -S02NH(CH2)3N{(CH2)3CH3}2 m=2 Formula (10-3&gt) ; L = -S02NH(CH2)2N(C2H5)2 m=2 Formula (1 0-4> L = -S02N(CH3)2 m=2 Formula (10-5) L = -S02N(C4H9)2 m= 2 Formula (1 0-6) L = -S02NH(CH2)3N(C2H5)(CH3) m=2 Formula (1 0-7) L = -S02NH(CH2)3N(CH3)2 m=2 Formula (1 0-8) L = -S02NH(CH2)2N(CH3)2 m=2 Formula (10-9> L = *S〇2—NN-CH3 m=2 (Specific example of azo dye derivative) Azo Specific examples of the dye derivative include compounds represented by the following formulas (11), (12), and (13), but are not limited thereto.

38 323842 201233734 Η . like

Formula (1 1) Formula (1 1-1) Formula (1 1-2 > Formula (1 Bu 3) Formula (1 Bu 4) Formula (1 1 - 5 ) L1 = —OH L2= —NH(CH2)4N (C2H5)2 L'= -OH L2=—NH(CH2)3N(C is)2 LU -NH(CH2)3N(C2H5)2 l2 = —nh(ch2)3n(c2hs)2 L1=—NH( CH2)2N(C3H7)2 l2=-NH(CH2)3N(C2H5)2 L2= -NH(CH2)s

L1 * one OH

Formula (1 1 - 6 ) CONH(CH2)2 -~VcH3 -NH-^~~^-CONH(CH2)2 - Formula (1 Bu 7) Formula (1 1-8) -NH-^~^~CONH (CH2)2N(C2H4OH)2 CONH(CH2)2N(C2H4OH>2 -NH-^^-CONH(CH2)2N{CH(CH3)2}2 -NH-^^-CONH(CH2)2N{CH( CH3) 2} 2

Formula (1 1 -9 ) L1= -NH(CH2)2N(CH3)2 l2= -NH(CH2)2N(CH3)2 323842 39 201233734

N=N_^Q_L2 NHCOCHCOCH3 Formula (12-1) L' = —ch3 Formula (1 2-2> L1 = One CH3 Formula (12-3) L1 = One ch3 Formula (1 2-4) L1: -ch3 (12-5) L1 = -och3 Equation (12-6> L1 = one och3 Equation (12-7> L1 = -och3 Equation (12-8) L1 = —och3 Equation (12-9) L1 = —N02 (1 2-10) L1: —N02 Equation (12-1 1) L1: —N〇2 Equation (1 2-1 2) L1 = One N02 Equation (1 2) L2= -conh(ch2)2n(c2h5 ) 2 L2= -conh(ch2>3n(c2hs)2 L2= -S02NH(CH2)2N(C2H5)2 L2= -S02NH(CH2)3N(C2H5)2 L2= -CONH(CH2)2N(C2H5)2 L2= -CONH(CH2)3N(CzHs)2 L 2 = —S02NH(CH2)2N(C2H5)2 L2= —S02NH(CH2)3N(C2H5)2 L2= —CONH(CH2)2N(C2Hs)2 L2 = -CONH(CH2)3N(C2H5)2 l2= —S02NH(CH2)2N(C2H5)2

Lz=一S02NH(CH2)3N(C2H5>2 Formula (1 3) / /N=N^Q-L3 L1-^ >-nhcochcoch3 Formula (13-1) L1 = One CH3 l2 = —ch3 l3 = - Conh(ch2)2n(c2h5)2 Formula (13-2) L1: —CH3 l2 = One CH3 l3 = —conh(ch2>3n(c2h5)2 Equation (13-3) L1: One ch3 l2 = -ch3 L3 = -S02NH(CH2)2N(C2Hs)2 Equation (13-4) L1 = -ch3 l2= —ch3 L3= -S02NH(CH2)3N(C2H5)2 Equation (13-5) L1 = -so3h l2 = one N〇2 L3=—CONH(CH2)2N(C2H5)2 Equation (1 3 - 6) L1 = -S03H l2 = —N〇2 L3= -CONH(CH2)3N(C2H5)2 Equation (13-7) L1: —so3H l2 = —N〇2 L3= —S02NH(CH2)2N(C2H5)2 Equation (13-8) L1 = -S03H l2= One N02 L3= -S02NH(CH2)3N(C2H5)2

(Specific Example of Quinone Derivative) The anthrone derivative is specifically a compound represented by the following formula (14-1) to formula 40 323842 201233734 (14-13), but is not limited thereto.

CI

(c2h5) 2n(h2c)3hn

41 323842 201233734

Formula (14-5) Formula (14-6)

Formula <14-7)

OC2H4N(C4H9)2 Formula (1 4-8)

OH NHCH

Formula (14-9>

c〇NH_<p^ ho3s/

NHCH 323842 42 201233734

Cl

(Specific Example of Quinone Derivative) The compound of the following formula (15) can be specifically used as the quinophthalone derivative, but is not limited thereto. 323842 43 201233734

Formula (1 s) Formula (15-1 > Formula (15-2 > Formula (1 S-3) Formula (1 5-4) Formula (1 5-5) Formula (15-6) Formula <15-7 )

L =: —〇H ms2 L = -COOH m=2 L = —S03H m=2 La -so2nh(ch2)4 is called CH3>2 L* -S02NH(CH2)2N(C2H5)2 m«2 L = one Ch2nhcoch2ch2n(ch3>2 ms2 L* -ch2nhcoch2mhch2n(c2h5>2 m«2 ,Η2 L = -C mS=1 (1 5-8) 0

(average primary particle size of pigment)

Or the fraction =: ί-like pigment composition, preferably having a particle size distribution with a very small particle size [cloth width narrowness]. By means of a daily implementation of the 贞 组成 组成 型 ; = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = It is difficult to disperse. Further, if it is larger than 70 (10) ..., the method obtains a sufficient contrast ratio. For this reason, a preferred range is 40 nm. By synthesizing pigments and mixing them to form a phase-to-construction stage 'average': when the (four) t is used for the upper occupation, it can be used directly. However, if it is not, the pigment should be finely polished by salt polishing, etc. 323842 44 201233734 and Whole granulation. (Purification of the pigment) The pigment containing the diketopyl π-pyro- and TJ-pyro pigment composition of the first embodiment is preferably used for refining, and the refining method is preferably 雎 grinding treatment ❶ ' The salt grinding treatment uses a kneader, a three-mixer, two roller mills, three roller mills, a ball mill, and a vertical ball mill (attrit〇r) for the mixture of the pigment, the water-soluble inorganic salt and the water-soluble organic agent. , sand mill and other training machines - while heating and mechanical mixing, by water to remove water-soluble inorganic salt water soluble organic solution treatment. The water-inorganic recording plays a role as a crushing aid. When the salt is ground, the high hardness of the inorganic salt is used to break the pigment, and the crystal is grown by the ®®. Therefore, during the kneading, the crushing and crystal growth at the same time are produced, and the diameter of the mixed strip is different. ^ The part that is paid (4) - times _ is promoted by heating to promote crystal growth. The heating temperature is less than 35. (: When the temperature is not 35 ° C to 150 ° C) The shape of the particles is close to the mosquito shape. The other side: the crystal grows, while the crystal growth progresses excessively, and the pigment heat temperature exceeds the 15th generation of the grinding. The time is larger from the size of the flat shame. In addition, the salt required for the two-knife cloth and the salt grinding treatment, the point of purchase 'is preferably 2 to 24 small dark, when the salt is ground to treat the pigment, the particle size Very fine, and the width of the distribution = the optimum of the cow 'is available -: the pigment of the cloth. The width is 乍乍, with the particle size of (4); 323842 'Used in salt grinding treatment · Water-soluble inorganic salt can be used for gasification 45 201233734 Nano, cesium chloride, potassium hydride, sodium sulphate, etc. However, from the price point of view, it is advisable to use gasified steel (salt). The water-soluble inorganic salt is in terms of both treatment efficiency and production efficiency. The pigment (10) part by mass is preferably tempered to 2000 parts by mass of 'the optimum period of use to 12 (10) parts by mass. Further, the water-soluble organic solvent is used for the wet pigment and the water-soluble inorganic salt t = t as long as it is dissolved (mixed) in water and Substantially does not dissolve the 2 inorganic salts used, no However, in the salt polishing treatment, the temperature of the tit solvent tends to evaporate, so from the viewpoint of safety, it is preferably a high boiling point solvent having a boiling point of 120 C or more. 戊αΠ' can be used with 2 methoxyethanol, 2_butyl Oxyethanol, 2 (iso), 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol I ethyl ether, diethylene glycol monobutyl ether, triethylene glycol ether, liquid Polyethylene glycol, B-known early 'propanol, one stone' _ 1 methyl ketone-2-propanol, 1-ethoxy-2, propylene glycol, dipropylene glycol monomethyl shrine, dipropylene B (tetra), ^ parts of diol, etc. The water-soluble organic solvent is based on the pigment component, and is used in an amount of 5 to 1000 parts by mass, preferably 50 to 500 mass, in order to improve the kneading efficiency. The granulation is very effective. In the second-but not limited to the refinement of the three substances, it is preferable to use the above-mentioned pigment derivative, and the degree, that is, the amount of the phase derivative used, does not affect the range of the color tone. For the pigment 100 parts by mass It should be 0.5JL 40 parts by mass and 323842 'salt grinding treatment can also be used if necessary to add resin 46 20123373 There are no special restrictions on the type of resin. The resin used in natural resin, synthetic tree, natural resin (four), and resin for daily use = solid at room temperature, and water is not mixed. The -part portion can be ☆ in the feeder solvent. The resin 'more preferably the mass part' is preferably in the range of 5 to 200 parts by mass. It is relative to the pigment [second embodiment] (diketopipyrrole, Each of the color filter compositions of the second embodiment contains the desertification of the following formula (1), and each of the lines and the specific formula shown by the following formula (Β-2) Pigment = W "The pigment composition of each series, the mass ratio of the color of the material to the following formula (B-2) is 9 (1) The inventors of the present invention have accumulated elaborate research. Using C. L Pigment Red 254 (gasification two == fruit found) instead of the conventionally used brominated diketopyrrolo D to be thicker than B), the brightness is improved by the sheet. The feed material 'formula (1)) is based on the light color of the diketone-based scale. The ratio is based on the use of a diketone base in a specific ratio and the (y) (y), (y), symmetrically introduced substituents. And (4) pigments) (hereinafter referred to as "specific heterodiketones comparatively produced and can be made from pomelo", which can obtain high brightness, high film, and σ,,,,,,,,,,,,,,,, Filtered by ί:·ί Γ 可 可 可 可 可 可 可 可 可 可 可 可 可 可 可 可 可 可 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色 彩色Crystallization of pigments. 323842 47 201233734

Br

Formula (1) Formula (B-2) [In the formula (B-2), A and B are each independently a hydrogen atom, a gas atom, a gas atom, a helium atom, a nitrogen group, and a carbon number of 1 to 12, Phenyl group having a substituent, _call, -(10), -SR2, -N(R3)R4, -C00R5, C0NH2, _c〇nhr6, _c〇n(r7)r8, -S〇2NH2, -S〇2NHR9 Or -SO^R^R11, R1 to R11 are each independently an alkyl group having a carbon number of i to 12, a phenyl group which may have a substituent, or an aryl group which may have a substituent; but A and B are not simultaneously A hydrogen atom]. The alkyl group having 1 to 12 carbon atoms may be linear or branched, and specifically may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a benzyl group or a second butyl group. Dibutyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, 1,5-didecylhexyl, 1,6-dimethylheptyl, 2-ethylhexyl, etc., but It is not limited to this. The phenyl group which may have a substituent may, for example, be an alkyl group having a carbon number of 1 to 4, a difluoromethyl group, a halogen atom, a schlossyl group, an aryl group, an amine oxime group, an amine sulfonyl group, and a carbon number of 1 to A phenyl group of a substituent such as an alkoxy group. The phenyl group may have one or two or more such substituents. More specifically, for example, benzene 323842 48 201233734, p-nonylphenyl, 4-tert-butylphenyl, p-nitrophenyl, p-methoxyphenyl, p-chlorophenyl, 2, 4- Dichlorophenyl, 3-aminoformylphenyl, etc., but are not limited thereto. The above aralkyl group which may have a substituent may, for example, be an alkyl group having a carbon number of 1 to 4, a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, an amine fluorenyl group, an amine sulfonyl group, or a carbon number. An aralkyl group having a substituent such as an alkoxy group of 1 to 4. The aralkyl group may have one or two or more such substituents. More specifically, it may, for example, be benzyl, 4-nonylphenyl fluorenyl, 4-tert-butylbenzyl, 4-decyloxybenzoyl, 4-nitrobenzyl, 2, 4 - Dichlorophenyl fluorenyl group or the like, but is not limited thereto. Specific examples of the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2) are exemplified below. However, it is not limited to this.

323842 49 201233734

Formula (B--4a) Formula (B-2-4b> Formula (B-2-4C)

323842 50 201233734

323842 51 201233734

323842 52 201233734

In the formula (B-2) used for the pigment composition, the color phase, the contrast ratio, and the effect of suppressing the precipitation of crystals are expressed by the formula (B-2-1), the formula (B-2-2), and the formula (B). B-2_4a), formula (B-2-6b), formula (B-2-7), etc. are preferred. The ratio of the formula (1) to the formula (B_2) in the pigment composition is in the range of 97.3 to 85:15 by mass. When the ratio of the formula exceeds 15% by mass, the effect of suppressing the crystallization precipitation can be obtained, but the excellent color tone of the formula (1) is caused by the color tone of the diketone fluorenyl ytterbium ytterbium ytterbium ytterbium pigment of the formula (1) is superior to the formula ( Β 2) The special azetodione group 0 is slightly smaller than that of Luoyan. On the other hand, when the ratio of the formula (?2) is less than 3% by mass, the effect of high contrast and crystallization precipitation inhibition is insufficient. When the effect of suppressing the crystallization precipitation is insufficient, light scattering occurs due to precipitation of crystal foreign matter on the surface of the coating film in the heating step, and the luminance 323842 53 201233734 and the contrast ratio are lowered. Therefore, by using the above-mentioned mass ratio range of two @同基吼 吼 吼 系 颜料 pigment composition, high brightness and high contrast can be achieved, and the crystal of the diketopyrrolopyrole pigment can be suppressed even if it is caused by the heating step. Precipitate. The pigment composition may be used in combination with the diketopyrrolopyrrole pigment of the formula and the diketopyrrolopyrrole other than the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2). It is a pigment. Further, in the case of the diketopyrrolopyrrole pigment of the formula (1) and the diketone-based pigment other than the specific heterodiketopyrrolopyrrole pigment B, the above formula (A- can also be used. 2) The specific heterodiketone ton σ each and the ratio of the pigment. At this time, the specific hetero-base 11 ratio shown by the formula (Α-2) is slightly shorter. The content of the specific conjugated pigment is preferably from 1% by mass to 15% by mass based on the total mass of the diketone ratio and the η ratio of the conjugated pigment. '*''' (Manufacturing method of diketopyrrolopyrrole pigment) The brominated diketone-based pyrrolepyrrole pigment of the formula (1) can be the same as the method of the first embodiment The way to manufacture. 'Specific heterozygous Β-pyrrolopyrrole pigment β of the formula (Β-2), for example, Synth· Commun., 1988, 18, 1213 and

Tetrahedron, 58 (2002) 5547-5565 The method for producing a human hetero-diketopyrrolopyrrole pigment B is not limited to this method. Further, the odorous diketone group β of the formula (1) can be used as a fine pigment composition simultaneously with a specific heterodiketo group of the formula (Β-2). And manufacturing. In the succinic acid diester synthesis method, at least two methods of constructing a different benzoate compound (hereinafter, referred to as "the two-shot co-synthesis method") can be used by 54 323 842 201233734. Specifically, in the method described in the above-mentioned WO 2009/081930 manual, the plural kinds of carbonitrile compounds used are obtained from 4-benzoic carbonitrile and benzoic acid compound represented by the following formula (B-3). The composition of the second embodiment of the dimercapto ruthenium pigment was selected.

Formula (Β - 3> [In the formula (Β-3), Α and Β are independently a hydrogen atom, a fluorine atom, a gas atom, a substituted atom, a cyano group, a filament having a carbon number of 1 to 12, and a benzene having a substituent. Base, m -SR2 ^ -N(R3)R^ , -C00r5 , .c〇NH2 ^ _c〇nhr6 ^ _c〇n(r7)r8 ^ -S〇2NH2, -S〇2_9, or -S〇2N( R1)Ru, R^RU are each independently a carbon group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent; however, A and B are not simultaneously a hydrogen atom]. The alkyl group having 1 to 12 carbon atoms, the phenyl group which may have a substituent, or the aralkyl group which may have a substituent is the same as the group in the above formula (B-2). The above aspect can be used in the second embodiment. Specific examples of the benzoquinone compound of the formula (B-3) are as follows, but are not limited thereto. 323842 55 201233734

NC^〇 nchQ^- nch〇-CF3 Formula (B_3_l) Formula (B_3_2> Equation (B-3-3)

Formula (B-3-6C) ^ (B-3-6 d) Formula (B-3-7) nc~~C3~°"~\ nc_^3~ci nc~^~^ Formula (B-3 -8) Formula (B-3-9) (B-3-1 0)

Formula (B-3- 1 1)

ncO-〇- nc~〇-^~ (B — 3 — 13> (B-3 – 14)

Formula (B-3 - 16) Formula (B - 3-17) The pigment composition can be produced by separately producing a brominated diketopyrrazole and a hetero-keto group having a ratio of P to π and a B is formed after mixing, but in terms of ease of manufacture, it is desirable to simultaneously manufacture a pigment composition by a co-synthesis method of a ship. If a separately produced compound is used, it can be dispersed before the two pigments are dispersed. In simple mixing, the powder 201233734 may be mixed by salt grinding treatment. If the brominated diketopyrrolopyrrole pigment of formula (1) is produced by co-synthesis of succinic acid diester, and the formula (B-2) When a pigment composition of a specific heterodiketopyrrolopyrrole pigment B is reacted with a mixture of 2 moles of 4-bromobenzenefonitrile and a benzonitrile compound of the formula (B-3) with respect to the oximeperic acid diester At this time, 'adjust the 4-kun carbonitrile to the compound of the formula (B-3), and the molar ratio of the compound (mole ratio) to form the diketopyrrolopyrrole pigment composition t. (1) The mass ratio to the formula (B-2) is 97: 3 to 85 to 15. Since the reaction & may vary depending on the type of the benzonitrile compound of the formula (B-3), 4_ Mixing ratio of benzonitrile to a benzoic acid compound of the formula (β'3) (Mohr ratio) ° In order to control the mass ratio of the diketone scaled pigment composition = the desired range '4- The mixed S ratio (mole ratio) of the silk carbonitrile to the benzonitrile compound of the formula (Β_3) is in the range of about 80: 2 Torr to 98 to 2. Further, in the 2-acid monoester co-synthesis method, although Can make! Moer's aloe vinegar, the opposite 2 Mo's (B-3) stupid carbonitrile compound should form a diketone, ie 'no silky two-time call and t each fight" but It is almost helmeted because of its extremely small amount. = two vinegar co-synthesis method: acid diterpene W compound ί reaction ratio, although relative to 1 mole of broken (four) two 酉, basically make 2 moles 'but as the use of benzene to guess the amount of compound, phase glass When the bribe vinegar is large and the excess is about 25 mol%, it can be effectively improved.

The pigment composition produced by the agglomeration method, the deserted diketone scaled scale pigment and the specific miscellaneous squash pigment B 323842 57 ϋ 201233734 can be compared with the first implementation The mass in the pattern is analyzed the same as the analytical method. (Pigment Derivative) ^& The pigment composition of the second and the first aspect of the pigment composition can be used for the purpose of suppressing the growth of the pigment crystal and further improving the pigment dispersibility. Examples of the pigments and organisms include the same pigment bamboos as the pigment derivatives of the first embodiment. The suitable amount of the pigment derivative used is also the same as that of the first embodiment. ~ • (average primary particle size of the pigment) The second embodiment of the diketone-based slightly squama pigmented sheet is preferably a sub-granule, very fine, and has a narrow distribution width and a fine particle size distribution. . The average-secondary particle diameter (number average particle diameter) of the diketone t squamous pigment composition of the second embodiment is determined by TEM (transmission electron microscope), preferably in the range of 5 to 70 nm. in. If it is less than - it may be difficult to disperse in an organic solvent. Also, if it is larger than 7 〇 nm, it may be impossible to obtain a sufficient contrast ratio. For this reason, the preferred range is from 1 〇 to 4 _. In the stage of producing the bismuth oxime by the above-mentioned synthesis method, and in the stage of the pigmentation, it is possible to use it directly when the average primary particle diameter is in the above range. However, if it is not, it is desirable to first perform salt polishing treatment or the like. The pigment is refined and granulated. (Refinement of Pigment) The pigment containing the bis-base% of each of the scaly pigment compositions of the second embodiment is used to make it fine and then used as a ruthenium. The method of miniaturization is preferably a bar grinding treatment. [Processing can be performed in the same manner as in the first embodiment (323842 58 201233734. [Coloring composition for color filter] Next, a coloring composition for a color filter in an embodiment of the present invention will be described. (3) (Coloring composition for color filter) The coloring composition for color filters of the third embodiment contains the diketopyrrolopyrrole pigment composition of the first embodiment. (1) The dibenzyl β ratio of the embodiment can be used as a coloring composition by using together with the binder resin and the organic solvent, and the second embodiment can be used in combination. The ketopyrrole is a coloring agent other than the pigment composition. For example, a diketopyrrolopyrrole pigment composition of the second embodiment can be used. (Other coloring agents) The coloring composition of the implementation can be In addition to the non-destructive and the range of the effect, the pigment or dye other than the diketopyrrolopyrrole pigment composition of the first embodiment may be used alone or in combination of two or more. When the coloring agent other than the pigment composition is used, the diketopyrrolopyrrole pigment composition of the second embodiment is preferably 30% by mass in the total amount of the coloring agent (1% by mass). The range of 1% by mass is preferably in the range of 50% by mass to 100% by mass. When the diketopyrrolopyrrole pigment composition of the i-th embodiment is less than 30% by mass, it is possible to cause brightness. 323842 59 201233734 (Binder Resin) The binder resin contained in the coloring composition may be a conventionally known thermoplastic resin or thermosetting resin. Further, in the fifth embodiment, the fifth embodiment can be used. Binder resin (CB) containing an alkali-soluble photosensitive resin (C-B1) As the binder resin, a resin (D-B1) containing the constituent elements (D_bl) to (D_b3) having the sixth embodiment can also be used. Adhesive resin (DB The thermoplastic resin may, for example, be an acrylic resin, a butadiene resin, a stupid ethylene-maleic acid copolymer, a vaporized polyethylene resin, a chlorinated polypropylene resin, a polystyrene resin, a polystyrene-vinyl acetate. Resin copolymer, polyvinyl acetate, urethane resin, polyester resin, vinyl resin, alkyd resin, polystyrene resin, polyamide resin, rubber resin, cyclized rubber resin, Cellulose, polyethylene (HDPE, LDPE), polybutadiene, and polyimide resin. When used as a coloring composition for color filters, it is preferably in the full-wavelength region of 400 to 700 nm in the visible light region. The resin having a spectral transmittance of 8 Å/Å or more is preferably 95% or more. Further, when it is used in the form of a base-developing coloring resist, an alkali-soluble vinyl-based resin obtained by copolymerizing an ethylenically unsaturated monomer having an acidic group is preferably used. Further, in order to improve the light sensitivity, an energy ray-curable resin having an ethylenically unsaturated active double bond may also be used. The soluble ethylene-based resin which copolymerizes the ethylenically unsaturated monomer containing an acidic group may, for example, be a resin having an acidic group such as a carboxyl group or a sulfonic acid group. Specifically, the alkali-soluble resin may, for example, be an acrylic resin having an acidic group, an olefin/(anhydrous) maleic acid copolymer, a styrene/styrene 323842 60 201233734 sulfonic acid copolymer, or an ethylene/(meth)acrylic acid copolymer. Or isobutylene / (anhydrous) copolymer of maleic acid and the like. Among them, it is preferable to use at least one resin selected from the group consisting of an acrylic resin having an acidic group and a styrene/styrenesulfonic acid copolymer, particularly an acrylic resin having an acidic group, to improve heat resistance and transparency. 'Therefore applicable. An energy ray-curable resin having an ethylenically unsaturated active double bond, which can be used in a polymer having a reactive substituent such as a thiol group, a thiol group, or an amine group, and having an isocyanate group, an aldehyde group, and an epoxy group. After reacting with a (meth)acrylic compound or cinnamic acid which is a reactive group, a photocrosslinkable group such as a (fluorenyl) acrylonitrile group or a styryl group is introduced into the polymer. Further, a polymer containing an acid anhydride such as a styrene-cis-butadiac dicarboxylic acid copolymer or an olefin-maleic anhydride copolymer may be used, and a hydroxyl group such as a hydroxyalkyl ester of (mercapto)acrylic acid ester may be used. (曱-based) acrylic compound and semi-defective. It is also a thermoplastic coloring agent that has both solubility and energy ray hardening properties, and is also suitable as a photosensitive coloring composition for color filters. The monomer constituting the above thermoplastic resin may, for example, be the following compound. For example, (mercapto) decyl acrylate, (mercapto) acrylate, (mercapto) n-propyl acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, (methyl ) isobutyl acrylate, (butyl) acrylic acid, third butyl vinegar, (meth) acrylate 2-ethylhexyl acrylate, (decyl) hexyl hexyl acrylate, (mercapto) acrylic acid octagonal vinegar, ( Mercapto) acetic acid eleven appearance. vinegar, tetrahydro 11 furan (fluorenyl) acrylate, (decyl) isodecyl acrylate, (meth) acrylate, (fluorenyl) benzoquinone Ester, phenoxyethyl (meth) acrylate, phenyloxy diethylene 323842 61 201233734 alcohol (meth) acrylate, methoxy polypropylene glycol (meth) acrylate or ethoxy polyethylene glycol ( (meth) acrylates such as acrylates; or (meth) acrylamide, N, N-dimercapto (meth) acrylamide, N, N-diethyl (methyl) propyl a thin amine, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide or acrylonitrile or the like (mercapto) acrylamide; Styrenes such as styrene or α-methylstyrene; vinyl ethers such as ethyl vinyl ether, n-propyl ethoxylate, isopropyl vinyl ether, n-butyl vinyl ether or isobutyl vinyl ether, acetic acid A fatty acid such as ethylene or propionate ethylene. Turtle or cyclohexyl cis-butyl diimide, phenyl cis-butane quinone imine, fluorenyl-butyl butyl amide, ethyl cis-butyl diimide, 1,2-bis-butene Dimethyleneimine ethane, 1,6-bis-n-butylenediamine hexane, 3-m-butyleneimine propionic acid, 6,7-methylenedioxy-4-methyl- 3-cis-butyl diimide coumarin, 4, 4'-bis-s-methyleneimine diphenylmethane, bis(3_ethyl-5-methyl-4-s-butenylene) Amine phenyl)methane, ν, Ν, 3_phenylene dimethyleneimine, N,N,_丨,4_phenylene dimethylenebutene, N-(diphenyl) Maleimide, N-(2, 4, 6-tris), maleimide, N-(4-aminophenyl) maleimide, n_( 4-nitrophenyl) maleimide, N-phenylhydrazine, maleimide, N-bromomethyl-2,3-di-n-butyleneimide, amber Amine_3_maleimide benzoate, N_amber succinimide _3_succinimide propionate, N-type peryleneimine _4-cis Butylenediamine butyrate Substituted cis-butyl phthalate, N-[4-(2-benzimidazolyl)phenyl]butyleneimine, 9-m-butyleneimine acridine Amines. 323842 62 201233734 The thermosetting resin may, for example, be an epoxy resin, a benzoguanamine, a rosin-modified maleic acid, a musk-modified succinic acid resin, or a melamine. Resin, urea resin, phenol resin, and the like. Among them, epoxy resin and melamine resin are suitable for improving heat resistance. The mass average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, and preferably in the range of 7, 〇〇〇 to 5 〇 in order to allow the colorant to be well dispersed. Further, the number average molecular weight (Mn) is preferably in the range of 25 to 40,000, and the value of Mw/Mn is preferably 10 or less. Here, the mass average molecular weight (Mw) and the number average molecular weight (Mn) are molecular weights converted to styrene measured by a gel permeation chromatography apparatus "HLC-8120GPC" manufactured by Tosoh Corporation. The separation column of the chromatograph is four in-line connections, and the filler is used in order to use "TSK-GEL SUPER H5000", "Η4000", "Η3〇θ〇〇" and "Η2000" manufactured by Tosoh Corporation. 'The mobile phase is tetrahydrofuran. When a binder resin is used as a composition for a color filter, it is desirable to consider a pigment adsorption group and an alkali-soluble carboxyl group at the time of development, a pigment carrier, and an aliphatic group acting as an affinity group with respect to a solvent. The balance between the base and the aromatic group. As the pigment dispersibility, developing property and durability, a resin having an acid value of 20 to 300 mgKOH/g is preferably used. If the acid value is less than 2 〇 mg K 〇 H / g, the solubility with respect to the developing liquid is lowered, and it is difficult to form a fine pattern. When the acid value exceeds 300 mgKOH/g, it is possible to develop without leaving a fine pattern. The binder resin may be used in an amount of 2 〇 323842 63 201233734 to 500 parts by mass relative to 100 parts by mass of the colorant. When the amount is less than 20 parts by mass, the film formability and various kinds of resistance may be insufficient. When the amount is more than 500 parts by mass, the pigment concentration may be lowered. ..... (Organic solvents)

In order to sufficiently disperse and impregnate the colorant in the colorant carrier, it is easy to apply on a substrate such as a glass substrate to form a dried film having a thickness of 〇 2 to 5 cm, and a filter segment is formed to form a coloring composition. Contains organic (4). The organic solvent is selected in order to improve the coatability of the colored composition, and the solubility and safety of each component of the colored composition are selected. For the purpose of the organic solvent, the cut coloring composition is adjusted to a moderate concentration to form a (four) thick (four) light segment, so that it is preferably used in an amount of 500 to 4 parts by mass relative to the mass of the coloring agent. (Method of making coloring composition)

The color composition is in the above-mentioned retanning agent resin and organic solvent-shaped coloring agent carrier, using a kneader, a 2_grinder, 3 mash grinders, a ball mill, a horizontal sand mill, a vertical sand mill, Various dispersing methods such as ring-type granule mill (annUlar, type beads miu) or vertical ball mill make the above-mentioned bismuth and D-type bismuth pigment composition finely dispersed to produce ^ ° and 'can also be two Each of the scaly pigment compositions is dispersed on the colorant carrier simultaneously with other colorants and the like to form a colored composition, which may be separately dispersed and dispersed on the colorant carrier to form a mixed composition. (Dispersing Aid) 继 散 323842 64 201233734 散=剂 The effect of re-agglomeration of the coloring agent after dispersing is large, so the coloring composition formed by the dispersing agent to disperse the coloring agent in the coloring agent carrier The object's contrast and viscosity stability is good. When the amount of the saponin-type dispersant or the surfactant is added, it is preferably from 0.1 to 55 parts by mass, and preferably from 〇. When the amount of the resin-type dispersant or the surfactant is less than 0.1 part by mass, the effect of addition is not easily obtained. For example, when the amount is more than 55 parts, the dispersion may be affected by an excessive amount of the dispersant. (Optional component) The coloring composition may contain, for example, the following components as optional components in addition to the dispersing agent. Specific examples of arbitrary components will be described later. (Photopolymerizable monomer and/or photopolymerization initiator) The coloring composition can be used as a photosensitive coloring composition after further adding a photopolymerizable monomer and/or a photopolymerization initiator. The photopolymerizable monomer to be used in the photosensitive coloring composition contains a monomer or an oligomer which can be cured by ultraviolet rays or heat to form a transparent resin. These may be used alone or in combination of two or more. The amount of the monomer is preferably from 5 to 400 parts by mass based on 1 part by mass of the colorant. It is preferably from 1 Torr to 3 (10) parts by mass in terms of photocurability and developability. After the composition is cured by ultraviolet irradiation, when the filter segment is formed by photolithography, it can be adjusted to be a solvent-developing type or a color-developing coloring resist material in addition to the photopolymerization initiator. form. The photopolymerization initiator is preferably 2 to 200 parts by mass with respect to 1 part by mass of the coloring agent in the photosensitive coloring composition, and is photohardenable and developable. 323842 65 201233734, 3 to 15 〇 mass Part is preferred. (Sensitizer) The photosensitive coloring composition may contain a sensitizer. The amount of the photopolymerization initiator (10 parts by mass) contained in the photosensitive composition is preferably 3 to 6 parts by mass in the case of using the sensitizer, and 5 to 6 in terms of photocurability and developability. 50 parts by mass is preferred. (multifunctional thiol)

The photosensitive coloring composition may contain a polyfunctional thiol which acts as a chain shifting agent. The polyfunctional thiol is preferably a compound having two or more thiol groups. Based on the mass of all the solid components of the photosensitive coloring composition (the content of the 100-mass polyfunctional thiol is preferably 〇. i to 3 〇 量 %, and is preferably from 1 to 20 by mass. Such as a polyfunctional thiol When the content is less than i% by mass, the effect of adding a polyfunctional thiol cannot be sufficiently obtained. For example, when it exceeds 3% by mass, it may cause the sensitivity to be too high and the resolution may be lowered. [Antioxidant] The coloring composition may contain Antioxidant. The anti-oxidant can prevent the photopolymerization initiator or the thermosetting compound contained in the coloring composition from being yellowed by the oxidation of the thermal step during the thermal hardening or ITO annealing, so that the coating can be improved. The penetration rate. iUb ' can be prevented from oxidizing and yellowing due to oxidation during the heating step, and a high coating film transmittance is obtained. Based on the solid content of the coloring composition (1 〇〇 mass %) The content of the antioxidant is preferably 0.5 to 5% by mass, because it is excellent in brightness and sensitivity. (Amine compound) 323842 66 201233734 The coloring composition of the composition may contain a solution for reductive dissolution. Oxygenation of oxygen The composition can improve the leveling property of the composition on the transparent substrate, and the coloring group (100V! Adding a leveling agent. Based on the total mass of the coloring composition, %. 1%) 'The content of the leveling agent is usually It is preferable to use 5% by mass of a curing agent or a curing accelerator. It is necessary to assist the curing of the thermosetting resin, and it is possible to have a curing agent or a curing accelerator depending on the mass of the coloring composition. The content of the above-mentioned hardening accelerator is preferably from 0 01 to 15 parts by mass based on 100 parts of the thermosetting resin. /, his additive component) stability In order to make __ viscosity stability, the coloring composition may contain stored stone, and in order to improve the adhesion with the transparent substrate, it may also be enhanced with the ceremonial mixture Agent. The total amount of the ochre is fresh ((10) f4%), and the storage stabilizer is preferably 0.1 to ίο% by mass. %) The total amount of the coloring agent of the 乂 coloring composition is based on the reference (100 mass-size adhesion enhancer is used in an amount of 0.01 to 10% by mass, and is preferably % by mass. · minutes = and 'outside the above-mentioned hiding ingredients Any one of the following may be included. (Removal of the plate-poles) The color composition of the 32-color composition is preferably a coarse particle of 5 or more by a centrifugal separation, a sintered filter membrane, or a membrane filtration membrane 67 201233734. And the mixed dust is removed, and the coarse particles are preferably lvm or more, and more preferably 〇.5//m or more. Preferably, the colored composition is substantially free of particles of μ 5 μ m or more. 3/zm or less. [Fourth embodiment] (Coloring composition for color filter) The coloring composition for a color filter according to the fourth embodiment contains the diketone group of the second embodiment. A pyrrolopyrrole-based pigment composition. The diketopyrrolopyrrole pigment composition of the second embodiment can be used as a coloring composition in combination with a binder resin and an organic solvent. Alternatively, the second embodiment can be used in combination. a form other than a diketopyrrolopyrrole pigment composition For example, a diketopyrrolopyrrole pigment composition of the second embodiment can also be used. (Other colorants) The coloring composition can be used in the range in which the effect is not impaired, in order to adjust the color, and the second color is used. When a pigment or a dye other than the diketopylpyrazole pyridin pigment composition of the embodiment is used, it may be used alone or in combination of two or more. When a coloring agent other than the diketopyrrolopyrrole pigment composition is used in combination, The di-based pyrrolopyrrole pigment composition of the second embodiment is preferably from 3% by mass to 9% by mass, and preferably from 60% by mass to 100% by mass, based on the total amount of the coloring agent (100% by mass). When the composition of the second steel-based pyrrolopyrrole pigment of the second embodiment is 4% by mass or less, there is a possibility that the excellent effect of brightness and contrast may not be sufficiently exhibited. (Binder resin) 323842 68 201233734 Color composition Examples of the binder resin contained in the resin include a conventionally known thermoplastic resin and a thermosetting resin. Examples of the binder resin include the same adhesive as the binder resin in the third embodiment. The binder is preferably used in the same manner as in the third embodiment. (Organic solvent) In order to sufficiently disperse and impregnate the colorant in the colorant carrier, it is easy to apply on a substrate such as a glass substrate. After forming a dried film having a thickness of 至2 to 5/Zm, a filter fragment is formed to contain an organic solvent in the colored composition. The organic solvent can be selected in the same manner as the selected method in the third embodiment. The amount of the suitable use is the same as that of the third embodiment. (Method for Producing Colored Composition) The colored composition of the fourth embodiment can be produced by the same manufacturing method as the method for producing the colored composition of the third embodiment. (Optional component) The coloring composition of the fourth embodiment may contain a dispersing aid, a photopolymerizable monomer, and/or a photopolymerization initiator, a sensitizer, a polyfunctional thiol, an antioxidant, and an amine system. Any component such as a compound, a leveling agent, a hardener, a hardening accelerator, and its additives. Specific examples of such arbitrary components are the same as in the third embodiment. Further, a suitable example, an appropriate amount of use, and the like are also the same as in the third embodiment. (Removal of coarse particles) The coloring composition of the fourth embodiment is the same as that of the third embodiment, and it is preferable to remove coarse particles. [Fifth Embodiment] 323842 69 201233734 (Coloring composition for color filter) The coloring composition for a color filter according to the fifth embodiment contains a pigment (A), a binder resin (CB), and a solvent. The pigment (A) is a pigment (A1) represented by the formula (1), and the binder resin (CB) is an alkali-soluble photosensitive resin (C-B1). The coloring composition for a color filter of the fifth embodiment can be used as a photosensitive coloring composition. As a result of intensive research by the inventors of the present invention, it has been found that a coloring composition containing a brominated diketopyrrolopyrrole pigment (a formula (〇) and an alkali-soluble photosensitive resin) is used instead of the previously used CI Pigment Red 254 (chlorinated). A diketone fluorenylpyrrole pigment) can obtain a color filter having a high luminance, a high contrast ratio, and suppressing a high-definition filter segment due to crystallization of a heating step. A coloring composition for a color filter having a high brightness and a high contrast ratio can be provided, which not only does not generate a diketone ratio of 11 by a heating step, but also forms a sensitivity or a straight line in the formation of a sensitivity or a straight line. It is also excellent in the balance of necessary properties such as a good filter fragment such as φ. (Pigment (A)) The pigment (A) contains the pigment (A1) represented by the formula (1). "Pigment (A1)" 323842 70 201233734

Br

The brominated diketopyl group of the pigment (A1) represented by the formula (1) can be produced by the same method as the method of the first embodiment. By using the pigment (A1)' represented by the formula (1), a red composition having a higher luminance and a higher contrast ratio than that of the conventional one is obtained. Further, the diketopyrrolopyrrole pigment composition in the first embodiment can be used, and the diketopyrrolopyrrole pigment composition in the second embodiment can be used as the pigment (A). "Other pigments" φ The coloring composition may be used in combination with a pigment other than the pigment (A1), and may be used alone or in combination of two or more kinds of organic or inorganic pigments. Among the pigments, pigments having high color developability and high heat resistance are preferably used, and organic pigments are usually used. The organic pigment which can be used may, for example, be a diketopyrrolopyrrole pigment other than the pigment (A1); an azo pigment such as azo, diazo or polyazo; steel indigo, i-copper indigo Indigo-based pigments such as metal-free indigo; amine-based guanidine, diamine-based guanidine, pyrimidine, flavanthrone, 蒽_, fluorenone, fluorenone, violanthrone, etc. From Kunming 323842 71 201233734; quinacridone pigment; diterpene pigment; anthrone pigment; flower pigment; thiazolin pigment; isoporphyrin pigment; porphyrin lanthanide pigment; Quinoline pigments; threne pigments; metal miscellaneous pigments, and the like. Among these pigments, it is preferred to contain a diterpene ratio p selected from the group consisting of pigments (A1), and an antimony pigment, an azo pigment, a quinone pigment, an anthocyanin pigment, and a quinacridine. One or more pigments selected from the group consisting of ketone pigments, benzoimidazolone pigments, and quinoline pigments. These pigments are similar to the pigment (A1), and it is possible to easily adjust the color ratio of the red pigment to be adjusted, and is excellent in such good lightness or heat resistance. Further, examples of the inorganic pigment include barium sulfate, zinc oxide, sulfuric acid, yellow lead, zinc yellow, dark red (red iron oxide (dish)), cadmium red, navy blue (cyan), dark blue (indigo), and chromium oxide. Green, cobalt green, brown earth, titanium black, synthetic iron black, titanium oxide, iron oxide and other metal oxide powder, metal sulfide powder, metal powder and the like. Inorganic pigments can be used in combination with organic pigments to achieve a balance between saturation and brightness while ensuring good coatability, sensitivity, and photographic properties. When used in combination with a red pigment or a yellow pigment, the content of the pigment (A1) represented by the formula (1) in the total amount of the pigment (A) is 40 to 1% by weight, and preferably 50 to 100% by weight, more preferably 60 to 1% by weight. The range of this content is preferably such that the color characteristics of the pigment (A1) represented by the formula (1) are sufficiently exhibited. In terms of sufficient color reproducibility, all of the coloring compositions are not. The content of the pigment (A) component in 100% by weight of the volatile component is preferably 1% by weight or more, more preferably 15% by weight or more, and particularly preferably 20% by weight or more. Further, 323842 72 201233734, the content of the pigment (A) component is preferably 90% by weight or less, more preferably 80% by weight or less, and particularly preferably 7% by weight or less, in order to improve the stability of the coloring composition. In the photosensitive coloring composition, a dye may be contained for coloring in a range in which heat resistance is not lowered. <<Refinement of Pigment>> The pigment (A1) and other pigments should be used in a fine manner. The fine particle size of the finely divided pigment is preferably 20 nm or more in terms of good dispersion in the colorant carrier. Further, since a filter segment having a high contrast ratio can be formed, it is preferably 100 nm or less. It is particularly excellent in the range of 25 to 85 nm. At the same time, the primary particle diameter of the pigment can be measured by direct measurement by the electron micrograph of the TEM (transmissive electron microscope) of the pigment. Specifically, after measuring the short diameter and the major axis diameter of the primary particles of each pigment, the average is taken as the particle diameter of the pigment particles. Next, for 100 or more pigment particles, the volume of each particle is approximated to the cube of the grain position to obtain an average volume, and the length of one side of the cube having the average volume is taken as the average primary particle diameter. Further, the specific surface area determined by the BET method of the fine pigments is preferably from 60 m 2 /g to 130 m 2 /g. If the specific surface area of the pigment (A) is less than the lower limit value, the brightness or contrast ratio of the color filter may be lowered. When the specific surface area is larger than the upper limit value, it may be difficult to disperse the pigment, and it is difficult to maintain the stability as a coloring composition, and it is difficult to ensure fluidity. As a result, the brightness or contrast of the color filter may be degraded. In the method of controlling the specific surface area of the pigment, there is a method of controlling the specific surface area by mechanically pulverizing the pigment 323842 73 201233734 (referred to as a grinding method), and putting the pigment dissolved in the good-content agent into a poor solvent, and then depositing the desired A method of a pigment having a specific surface area (referred to as a precipitation method), a method of producing a pigment having a desired specific surface area during synthesis (referred to as a synthetic precipitation method), or the like. An appropriate method can be selected for each pigment to control according to the synthesis method or chemical properties of the pigment. Any of the above methods may be used as a method of controlling the specific surface area of the pigment contained in the colored composition. The pigment used in the fifth embodiment is preferably finely refined by a salt grinding treatment in a grinding method, and a filter having a high contrast ratio can be formed by using such a pigment. The salt grinding treatment is carried out in the same manner as in the above diketopyrrolopyran pigment composition. (Binder Resin (C-B)) The binder resin (C-B) is a resin which disperses the pigment (A) and contains an alkali-soluble photosensitive resin (C-B1). <<Alkali-soluble photosensitive resin (C-B1)>> The alkali-soluble photosensitive resin (C-B1) is, for example, introduced into the ethylenically unsaturated double by the (Ci) or (C-Bii) method shown below. The resin of the bond. &lt;Method (Ci)&gt; The method (Ci) is, for example, on a side chain epoxy group of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having an epoxy group with one or more other monomers. a slow-radical addition reaction of an unsaturated monobasic acid having an ethylenically unsaturated double bond, and reacting a polybasic acid anhydride onto the generated hydroxyl group to introduce an ethylenically unsaturated double bond to have a function as a photosensitive resin, and A method of introducing a carboxyl group having an alkali-soluble function. 323842 74 201233734 Ethylene-containing unsaturated monomer having an epoxy group, for example, glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidyloxy (meth)acrylate Ethyl acetate, 3, 4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate, these monomers may be used singly or in combination of two or more. In view of the reactivity of the first step with the unsaturated monobasic acid, it is preferred that the (mercapto) acrylose glycidol be used. Examples of the unsaturated monobasic acid include (mercapto)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, an α-haloalkyl group of (mercapto)acrylic acid, an alkoxy group, a halogen, an exact group, For example, a monodecanoic acid such as a cyano substituent may be used alone or in combination of two or more. Examples of the polybasic acid anhydride include tetrahydrofurfuric anhydride, decanoic anhydride, hexahydrophthalic anhydride, succinic anhydride, and maleic anhydride. These acids may be used singly or in combination of two or more kinds. When the number of carboxyl groups is increased, if necessary, a tricarboxylic anhydride such as trimellitic anhydride or a tetracarboxylic anhydride such as pyromellitic aciddianhydride may be used, and the residual φ acid anhydride group may be hydrolyzed or the like. . Further, when tetrahydrophthalic anhydride or maleic anhydride having an ethylenically unsaturated double bond is used as the polybasic acid anhydride, the ethylenically unsaturated double bond can be further increased. A method similar to the method (Ci), for example, a part of a side chain carboxyl group of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having a carboxyl group with one or more other monomers, and having a ring A method of introducing an ethylenically unsaturated double bond and an ester group after an addition reaction of an ethylenically unsaturated monomer of an oxy group. &lt;Method (C-ii)&gt; The method (C-ii) is, for example, an ethylenically unsaturated single 323842 75 201233734 having a hydroxyl group, a monomer or other monomer having an unsaturated monobasic acid having another carboxyl group. A method of reacting an isocyanate group of an ethylenically unsaturated monomer having an isocyanate group on a side chain hydroxyl group of a copolymer obtained by copolymerization. The ethylenically unsaturated monomer having a hydroxyl group may, for example, be 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2- or 3- or 4-(meth)acrylate. - (hydroxy) butyl acrylate, (meth) propylene hydroxy alkanoate such as cyclohexanedonol mono(indenyl) acrylate, these monomers may be used alone or in combination The above is used together. Further, it is also possible to add or polymerize a polyether mono(meth)acrylate or the like to ethylene oxide, propylene oxide, and/or butylene oxide on the above (meth) acrylate hydroxyalkane. An (poly)ester mono(meth)acrylate such as 7-valerolactone, (poly)ε-caprolactone and/or (poly)12-hydroxystearate. In the case of inhibition of the foreign matter of the coating film, it is preferably 2-hydroxyethyl (meth) acrylate or glycerin (mercapto) acrylate. Examples of the ethylenically unsaturated monomer having an isocyanate group include #2-(meth)acryloyloxyethyl isocyanate, or 1, bis[(indenyl)acrylenyloxy]ethyl isocyanate, and the like. However, it is not limited to these monomers, and two or more types may be used in combination. The alkali-soluble photosensitive resin (C-B1) may, for example, be an unsaturated monocarboxylic acid such as (meth)acrylic acid, crotonic acid or α-chloroacrylic acid, or maleic acid or fumaric acid. A resin obtained by a monomer having a carboxyl group such as an unsaturated dicarboxylic acid and having an ethylenically unsaturated double bond. Examples of the other ethylenically unsaturated monomer which is a precursor of the alkali-soluble photosensitive resin (C-B1) include methyl (meth)acrylate, ethyl (meth)acrylate, and (meth)acrylic acid 323842 76. 201233734 n-propyl vinegar, (mercapto) isopropyl isopropyl vinegar, (methyl) acrylic acid butyl milk, acrylic acid, isobutyl vinegar, (methyl) propylene glycol, second gambling, 曰: base) Vinegar, (meth)acrylic acid, (meth)acrylic acid, isoprene, propane = propenyl neopentyl acrylate, (p-butyl) methacrylate, methyl) mercaptobutyric acid, Methyl)acrylic acid, (methyl; octyl acrylate, 2-ethylhexyl acrylate, hydrazine, methyl) dialkyl ester, cetyl (meth) acrylate, ( Methyl)acrylic acid ten

(methyl) (tetra) acid octadepene, (mercapto) propyl ring 十 10 ^ duck, aryl acrylate or (mercapto) acrylate oil (meth) propylene methyl) (fluorenyl) propylene vinegar The corresponding purpose may not be limited to such a selection or selection of other ethylenically unsaturated monomers, and may also be used in combination of two kinds of = upper or in terms of pigment dispersibility, preferably (mercapto)-acid hydrazine, wherein acid B vinegar. The weight average molecular weight of the W methyl) 3⁄4 olefin-soluble photosensitive resin (C-B1) is preferably in the range of 5,000 to 100,000, preferably 5, 〇〇〇 to ^ 〇〇〇 (^), preferably, It is better in the range of 5,000 to 30,000. Further, the number average = norm, (Μη) is preferably in the range of 5,000 to 50,000, and the value of Mw/Mn is preferably sub-input. When the weight average molecular weight of the alkali-soluble photosensitive resin (C_B1) exceeds 100,000, the viscosity of the coloring composition for the L color filter becomes high due to the strong interaction between the resins, so that it is difficult to handle. Further, when the weight average molecular weight (Mw) is less than 5,000, the developability or adhesion to a substrate such as glass may be lowered. The acid value of the alkali-soluble photosensitive resin (C-B1) is preferably from 20 to 300 KOH-mg/g in terms of dispersibility, permeability, developability and resistance of the pigment. When the acid value is less than 20 KOH-mg/g as in 323842 77 201233734, the solubility in the developing solution is lowered, and it becomes difficult to form a fine pattern. If it exceeds 3 〇〇K〇H_mg/g, the fine pattern will not be retained. The content of the alkali-soluble photosensitive resin (C-B1) is preferably from 1 to 1% by weight, and preferably from 2 to 100% by weight, based on 1% by weight of the total of the binder resin (CB). More preferably from 40 to 100% by weight. When the content of the soluble photosensitive resin (c-βΐ) in the binder resin (C-B) is 1% by weight or more, it is easy to obtain a high brightness and high contrast effect of the colored composition. "Other resin" The binder resin (C-B) ' may contain a resin other than the alkali-soluble photosensitive resin (C-B1). The other resin is preferably a resin having a transmittance of 8 % or more in the entire wavelength range of 400 to 70 Å in the visible light region, and preferably 95% or more. For example, a thermoplastic resin, a thermosetting resin, etc. may be used singly or in combination of two or more kinds. The σ thermoplastic resin may, for example, be a Bacillus vinegar, a stupid ethylene-succinic acid copolymer, a chlorinated polyethylene, a chlorinated polypropylene, a polyvinyl chloride, a vinyl chloride-vinyl acetate copolymer, or a polyvinyl acetate. Polyurethane resin, polyester resin, acrylic resin, alkyd resin, polystyrene, polyamide resin, rubber resin, cyclized rubber resin, cellulose, polyethylene, polybutadiene, and polyaluminum Bribe. Further, the thermosetting transesterification may, for example, be an epoxy resin, a benzoic melamine resin, a rosin-modified cis-butyl dibasic acid resin, a rosin-modified anti-butyl bis-lipid, a melamine lysine, a urea resin, and a lin. Fat and so on. 323842 78 201233734 The thermosetting resin may, for example, be a benzoic melamine resin, a rosin-modified fat-butene-acid resin, a rosin-modified fumaric acid resin, a melamine tree 9 urea resin or a phenol resin. In addition, it is also possible to use a combination of an ethylenically unsaturated monomer containing an acidic group to form a soluble resin. The alkali-soluble resin may, for example, be a resin having an acidic group such as a carboxy a fluorenyl group. Specific examples of the soluble resin may be, for example, an acrylic resin having an acidic group, an olefin/(anhydrous)-buteneene 1 conjugate, a styrene/styrenesulfonic acid copolymer, and an ethylene/(meth)-propyl group Long-term copolymer or isobutylene / (anhydrous) maleic acid copolymer and the like. Among them, 2 is at least one resin selected from the group consisting of an acrylic resin having an acidic group and a stupid ethylene/styrenesulfonic acid compound, and particularly, an acrylic tree 9' having an acidic group is used because of its high heat resistance and transparency. The fat is 1 〇 0 parts by weight relative to the pigment (Α) in the coloring composition, the binder is used to transfer B) and used to 400 parts by weight 'to use 5 〇 to 250 parts by weight (> 容) (c solvent It is used to sufficiently disperse the pigment (A) in the binder resin and B). The coating composition is applied to a substrate such as a glass substrate to have a dry film thickness of 〇2 = to easily form a filter segment. The solvent is preferably an organic solvent. With respect to 100 parts by weight of the pigment (A), the solvent is preferably used in an amount of from 8 Å to 4' 00 parts by weight to adjust the coloring composition to a suitable viscosity to form a uniform film thickness. Fragment. (3⁄4 Method for the preparation of a light-colored composition) 323842 79 201233734 The production of a photosensitive coloring composition is performed by using three pro-grinding machines, two roll grinders, a kneader, a vertical ball mill, and the like. In a preferred manner, the pigment (A) is preferably dispersed in a pigment carrier such as a binder tree MC B) and a solvent together with a pigment dispersant to form a pigment dispersion, and then a photopolymerization initiator (CD), A binder resin (e_B), a silk fibroin compound, a sensitizer (CE) as needed, a polyfunctional thiol, a UV absorber, a polymerization inhibitor, a storage stabilizer, and other components are mixed in the pigment dispersion. In addition, the coloring group containing two or more types of pigments is a mixture of two types of pigments, and is a mixture of various pigment dispersions dispersed in a pigment carrier and/or a solvent. Remixing photopolymerization initiator (CD Or a photopolymerizable compound which can be produced after stirring. (Pigment Dispersant (CC)) When the pigment (A) is dispersed in the binder resin (C_B) and/or a solvent, a resin type pigment dispersant may be suitably contained. A pigment dispersant (CC) such as a pigment derivative or a surfactant. The pigment dispersant (c) can be used because the pigment dispersant (c_c) is excellent in dispersion of the pigment_, and the effect of re-agglomeration of the pigment after dispersion is large. When the pigment is dispersed in the coloring composition formed by the binder resin (C_B) and/or the solvent, a color filter excellent in transparency can be obtained. Particularly, in terms of the stability of the coloring composition, the coloring composition preferably contains an acidity. A resin-based pigment dispersant is preferably used in combination with an acidic resin-based pigment dispersant and an alkaline pigment derivative, because it is excellent in fluidity and stability of the coloring composition, and also excellent in high brightness and high contrast ratio. 1至30重量份。 Resin type pigments. The pigment dispersing agent (c_c) may be used in an amount of 323842 80 201233734 0. 1 to 40 parts by weight, and preferably 0.1 to 30 parts by weight. dispersion , surfactants, examples of resin-based pigment dispersants and surfactants are described later. "Pigment Derivatives" Pigment derivatives can be cited, for example, in organic pigments, 蒽cool, α-bittone or three-plowing. A compound formed of a basic substituent, an acidic substituent or a hydrazinium group which may have a substituent, and its structure is, for example, a compound represented by the following formula (50), and among them, a pigment derivative is preferred. P-Lm Formula (50) [In the formula (50), P: an organic pigment residue, an anthracene residue, an acridone residue or a tri-farming residue L: a basic substituent, an acidic substituent or a hydrazine which may have a substituent醯iminomethyl m: an integer of 1 to 4] For example, JP-A-63-305173, JP-A-57-15620, JP-A-59-40172, and JP-A-2013 The compound described in the above-mentioned Japanese Patent Publication No. 5-17469, or the like, may be used alone or in combination of two or more. In the formula (50), the organic pigment constituting the organic pigment residue of P may, for example, be a diketopyrrolopyrrole pigment; an even II pigment such as azo, diazo or polyazo; copper indigo; Amaranth pigments such as copper phthalocyanine, eucalyptus green, zinc halide phthalocyanine, and metal-free indigo; amine hydrazine, diamino hydrazine, hydrazine 323842 81 201233734 shouting, flavonoids, fluorenone, anthraquinone Ketone, ° ketone, purpurone, etc.; quinacridone pigment; diterpene pigment; anthrone pigment; tray pigment; thiazolin pigment; isoporphyrin pigment Isoporphyrin s homologous fabric; Shilin pigment; quinoline pigment; dioxin pigment; metal miscellaneous pigment. Among them, it is preferred to use a dye derivative of the formula which is a basic substituent of L in the formula (50). Even if the dye enamel/amplifier having an inactive substituent does not exist in a pigment which is not easily dispersed, it is possible to obtain dispersibility, fluidity, and preservation stability by containing a pigment derivative having a ridge substituent. The pigment composition can be effectively dispersed by the synergistic effect of the acidic resin type dispersant and the dye derivative having an inert substituent, and becomes a pigment composition excellent in viability and storage stability. Among the inert substituents, L is preferably a substituent selected from the group consisting of the formulae (51), (52) and (53). Formula (S 1) 323842 82 201233734 R52 R53

XCH-0H -N \j-R56 \ /

CH-CH (/54 R55

Formula (5 2)

Formula (5 3) [In the formulae (51) to (53),] X is -S〇2---CO-, -CH2---CH2NHCOCH2---CH2NHS〇2CH2- or direct bonding, Y is - NH---0- or direct bonding, k is an integer from 1 to 10, Y1 is -NH---NR58-Z-NR59- or a direct bond, and R58 and R59 are respectively independent hydrogen bonds and may have a substitution An alkyl group having 1 to 36 carbon atoms, an alkenyl group having 2 to 36 carbon atoms which may have a substituent or a phenyl group which may have a substituent, and Z is an alkylene group which may have a substituent or may have a substituent. An aryl group, R50 and R51 are each independently a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, or a combination of R5 and R51 a heterocyclic ring which may have a substituent containing a nitrogen, oxygen or sulfur atom, 323842 83 201233734 r52, r53, r54 and R55 are each independently a hydrogen atom, may have a substituent of a carbon number of 1 to 20, may have a substitution a dilute group having 2 to 20 carbon atoms, a aryl group having 6 to 2 carbon atoms which may have a substituent, R56 being a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and a substituent having an anthracene a carbon number of 2 to 20, R57 is the above The substituent represented by the above formula (52) or the substituent represented by the above formula (52), wherein Q is a hydroxyl group, an alkoxy group, a substituent represented by the above formula (51) or a substituent represented by the above formula (52) . The amine component used in the formation of the substituents represented by the formulae (51) to (53) is exemplified by the same amine component as the amine component in the first embodiment. A pigment derivative which may have a basic substituent can be synthesized by various synthetic routes. For example, 'the substituents represented by the formulas (54) to (57) are introduced into the organic pigment to react with the above substituents, and the amine component which can form the substituents represented by the formulae (51) to (53), for example, N,N-didecylaminopropylamine, φ I hydrazine, diethylamine or 4-[4-hydroxy-6-[3-(dibutylamino)propylamino]- 1, 3, 5-tricyano-2-ylamino] aniline can be obtained after the reaction. Formula (54): -S〇2Cl Formula (55): -C0C1 Formula (56): -CHNHCOCH2Cl Formula (57): -CH2Cl When the substituent of the formula (54) to (57) is reacted with the above amine component, ' After the partial substituents of the formulae (54) to (57) are hydrolyzed, they are mixed with a compound which substitutes a gas for a hydroxyl group. In this case, the formula (54) and the formula (55) may be respectively a sulfonic acid 323842 84 201233734 ^ a few of the bases, but also in the form of a free acid, or a metal of 1 to 3 or the above-mentioned single Amine salt. Further, when the organic pigment is an azo-based pigment, a substituent derived from the formula (51) to (53) is introduced into a diazo component or a coupling component in advance, and then a coupling reaction is carried out to produce an azo-based pigment. Things. The trimorphine derivative having an inert substituent can be synthesized by various synthetic routes. For example, 'the reaction of an amine component forming a substituent represented by the formula (51) to (53) on at least one gas of a trimeric vaporized cyanide using a trimeric gasification cyanogen as a starting material', for example, N, N_ Methylaminopropylamine or M-mercaptopiped, followed by reaction of residual chlorine of cyanuric chloride with various amines or alcohols. (Optional component) The coloring composition of the fifth embodiment may contain, for example, the following components as an optional component, in addition to the pigment dispersant. Specific examples of the optional components will be described later. (Photopolymerization initiator (CD)) φ In the photosensitive coloring composition, a photopolymerization initiator (CD) may be added to prepare a pattern of the photosensitive coloring composition, so that the composition It is hardened by ultraviolet irradiation to form a filter segment by photolithography. The photopolymerization initiator (C-D) is preferably contained in an amount of 5 to 2 parts by weight based on the weight of the pigment (A), and preferably 150 parts by weight in terms of photocurability and developability. (Sensitizer) The photosensitive coloring composition may contain a sensitizer. The content of the sensitizer is preferably from 3 to 6 parts by weight based on the photopolymerization initiator 323842 85 201233734 (CD) 100 parts by weight in the photosensitive coloring composition, in terms of photocurability and development. It is preferably 5 to 50 parts by weight. (Photopolymerizable Compound) The photosensitive coloring composition may contain a photopolymerizable compound. The photopolymerizable compound contains a monomer or a valence polymer which can be cured by ultraviolet rays or heat to form a resin. The content of the photopolymerizable compound (C-C) is preferably 10 to 3 parts by weight based on 100 parts by weight of the pigment (A), and is preferably _10 to 200 parts by weight in terms of photocurability and developability. (Polyfunctional Mercaptan) The photosensitive coloring composition may contain a polyfunctional thiol (C-F). The polyfunctional thiol is a compound having two or more thiol (SH) groups. By using a polyfunctional alcoholic alcohol simultaneously with the above-mentioned photopolymerization initiator (CD), in the radical polymerization process after light irradiation, a sulfur-based free radical which is less susceptible to oxygen hindering polymerization can be produced by acting as a chain shifting agent. The thiyl radical can be made into a high sensitivity. Particularly preferred is a polyfunctional aliphatic thiol having SH bonded to an aliphatic group such as a methylene group or an ethyl group. The content of the polyfunctional thiol is preferably from 0.05 to 1 part by weight, and more preferably from 1 to 5 parts by weight, based on the weight of the pigment (A). When the monofunctional thiol having one thiol (10) group is used, it is possible to obtain such a development resistance by using a polyfunctional thiol having a weight or more. (Ultraviolet ray and charge) The photosensitive coloring composition may contain an ultraviolet absorber. The shape and resolution of the pattern can be controlled by the inclusion of UV 323842 86 201233734 line absorber. The amount of the ultraviolet absorber is from 0.01 to 20 parts by weight, and preferably from 0.05 to 10 parts by weight, based on 100 parts by weight of the pigment (A). A better resolution can be obtained by using 0.01 part by weight or more of the ultraviolet absorber. (Prohibition of Polymerization Agent) The photosensitive coloring composition may contain a polymerization inhibiting agent. The shape and resolution of the pattern can be controlled by the inclusion of a polymer inhibiting agent. The amount of the polymerization agent is from 0.01 to 20 parts by weight, and is preferably from 0.05 to 10 parts by weight, based on 100 parts by weight of the pigment (A). A preferred resolution can be obtained by using 0.01 parts by weight or more of the inhibiting polymerization agent. (Storage Stabilizer) The photosensitive coloring composition may contain a storage stabilizer. The composition's time-dependent viscosity is stabilized by the presence of a storage stabilizer. 0至10重量份的量。 The amount of the storage stabilizer is 0. 01 φ to 20 parts by weight, and preferably used in an amount of 0.05 to 10 parts by weight. The stability of the colored composition can be improved by using 0.01 parts by weight or more of the storage stabilizer. (Other additives) The photosensitive coloring composition may contain an adhesion promoter such as a decane coupling agent to improve the adhesion to the transparent substrate or to act as an amine compound which reduces the dissolved oxygen. The amount of the adhesion promoter is from 0.01 to 10 parts by weight, and preferably from 0.05 to 5 parts by weight, based on 100 parts by weight of the pigment (A). 323842 87 201233734 曰— ^ In addition to any of the above components, it may contain any of the components described below. (removal of coarse particles)

The coloring composition of the flute G is also the same as the coloring composition of the third embodiment. It is preferable to remove coarse particles. [Sixth embodiment] The coloring composition for a color light-receiving sheet of the practical aspect is a coloring composition for a color filter containing a pigment #2 binder resin (DB) and a solvent; (A) is The pigment (A1) and the binder resin (D-β) of the formula (?) are each a resin (D-bi) having the following structural units (D-bl) to (D-b3). The coloring composition of the fine color filter can be used as a photosensitive coloring composition. As a result of intensive research by the present inventors, it has been found that the use of a brominated bis-pyrrolopyrrole pigment and a specific structure are used. The coloring composition of the binder resin, in place of the conventional CI Pigment Red 254 (gasified diketopyrrolopyrrolopyrrole pigment), can have high brightness, high contrast, and inhibit crystal precipitation due to the heating step. A color filter of a high-definition filter segment. According to the sixth embodiment, a coloring composition for a color filter having a high luminance and a high contrast ratio can be provided, which not only does not generate a diketone group due to a heating step. °The green crystal of the pirox and the bismuth pigment is precipitated and is used as the photosensitivity When a coloring composition is used, it is excellent in balance of necessary performance when forming a good filter segment such as sensitivity or linearity. (Pigment (A)) Pigment (A) is a pigment in the fifth embodiment (A) The same pigment, 323842 88 201233734 can be obtained by the same method as the production method in the fifth embodiment. Since the pigment (A1) represented by the formula (1) is used in combination with the resin (D-B1), In addition, a red coloring composition having a higher brightness and a higher contrast ratio than in the past can be obtained. The coloring composition of the sixth embodiment is also the same as the coloring composition of the fifth embodiment, and the pigment (A1) and other pigments can be used in combination. At the same time, the pigment (A1) and other pigments should be refined and used. (Binder resin (DB)) "Resin (DB)" Adhesive resin (DB) contained in the resin composition for color filters. The feature is a resin (D-B1) having the following structural units (D-bl) to (D-b3). (D-B1) A constituent unit having a carboxyl group: 2 to 60% by weight (D-b2) A constituent unit having an aromatic ring group represented by formula (D-2) or formula (D-3): 2 to 80% by weight (D-b3) having a formula Constituent units of the aliphatic cyclic group D-4) or Formula (D-5) shown below: 2 to 60 wt. ° / square 323 842 89 201 233 734

Formula (D-2)

In the formulae (D-3) and (D-3), R is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a benzene ring. The imaginary moiety in the formula (D-3) is a cyclic structure which is adjacent to the benzene ring and contains one or more saturated or unsaturated heterocyclic rings which may have a substituent. ]

Hereinafter, the order of the constituent unit (D-bl), the constituent unit (D-b2), and the constituent unit (D-b3) will be described. In this embodiment, the 323842 90 201233734 of each constituent unit has a weight of the precursor contained in the resin (D,) of each constituent unit &lt;constituting unit (D-bl)&gt;

J is early: (D Μ) has a carboxyl group, and is used as an alkali-soluble site in development: 二: The weight of all constituent elements of the two-component resin is based on the benchmark's performance stability, and the constituent unit (D-bl) is 2 Up to 60% by weight. If it is less than 2 weights, it will make the unexposed part 1 caused by the testability liquid 1 depleted, and the dispersion stability will be reduced. At the same time, if more than 60% of the star weight will make the dissolution rate of the test imaging liquid faster, and even dissolve into the exposed portion. The precursor of the constituent unit (D-bl) having a few groups may, for example, contain an unsaturated monocarboxylic acid such as (meth)acrylic acid, crotonic acid or α-chlorinated acrylic acid, or a butyric acid or a reversed butene A compound having an ethylenic unsaturated double bond such as a diacid or a non-saturated acid such as a diacid or the like. Further, a (meth)dienyl compound having a hydroxyl group such as a hydroxyalkyl (meth)acrylate may be used, and an acid anhydride of an unsaturated dibasic acid such as cis-butadidic acid may be semi-esterified. Among them, in terms of polymerizability (easiness in controlling molecular weight and the like), (meth)acrylic acid is preferred, and thioglycolic acid is particularly preferred. These compounds may be used singly or in combination of two or more. Even the precursor containing a carboxyl group in the raw material stage does not conform to the constituent unit (D-bl) when the carboxyl group is converted into an ester bond or the like by the step of forming the binder resin (D-B). &lt;Structural unit (D-b2)&gt; The constituent unit (D-b2) has a cyclic structure of aromatic 323842 91 201233734 represented by formula (D-2) or (D-3) as having a relative pigment The function of the affinity part of the formed pigment composition: the quality of the dispersion is one (four) fresh, and the imaging _, the light fragment. The composition of early indica (D-b2) is 20 to 80% by weight. If the pigment light sheet which is not formed by the pigment or the pigment and the dispersant is insufficient, there is a problem that the high-quality color s and the light fragment are not deteriorated; if it exceeds 8 〇, the w will make the test The speed of hiding is slower, and the productivity of the light film is deteriorated. To the color, the pigment (A1) represented by the formula (1) contains a bromine atomic ratio higher than that of the chlorine atom in the structure. Therefore, it contains aromas, ', and 'subjects' (D-b2), and it is expected that the redundant electrons will show a stronger affinity than the chlorinated dicentric = conformal η unit (CI Pigment Red 254).彳=slip pigment

R

Formula (D-2) [In the formula (D-2) and the formula (D-3), R is a burnt group having a ruthenium atom of 1 to 2 G. The dotted line in the formula (D-3), which has a stupid ring carbon, 1 pseudo 疋 represents the adjacent stupid ring 323842 201233734 and contains one or more saturated or unsaturated hetero-cao structures which may have a substituent. % of clothing The precursor of the constituent unit (D-b2) may, for example, be stupid ethylene, base ethylene, diethyl benzene, hydrazine, ethylene ring-burning hydrocarbon, benzyl methacrylate acrylate, double Monomer/oligomer such as phenolphthalein diglycidyl ether di(indenyl) di-n-butyl ester, methylolated melamine (meth) acrylate or ethylenic unsaturated monomer represented by formula (D-6) Body and so on.

Formula (D-6) [In the formula (D-6), R1 is a hydrogen atom or a fluorenyl group, R2 is an alkylene group having 2 or 3 carbon atoms, and R3 is an alkyl group having 1 to 20 carbon atoms which may have a benzene ring. , n is an integer from 1 to 15. _ The ethylene unsaturated monomer represented by the formula (D-6) is, for example, New Frontier CEA manufactured by Dai-ichi Pharmaceutical Co., Ltd. [E0 modified methotrexate g, ri · hydrogen atom, R2 : Ethyl, R3: methyl, n=l or 2], NP-2 [n-nonyl oxypolyethylene glycol acrylate, R1: 氲 atom, R2: ethyl, R3: 壬Base, n=2], N-177E [n-nonylphenoxy polyethylene glycol-propylation] R1: hydrogen atom, R2: ethyl group, R3: n-decyl group 16 to 17] Or PHE [phenoxyethyl acrylate, R1: hydrogen atom, R2: ethyl group, R3: oxygen atom, n = l],

Made by Daicel, IRR169 [ethoxylated acrylate (E〇323842 93 201233734 lmol), R1: hydrogen atom, R2: ethyl, R3: hydrogen atom, n=l] or Ebecry 1110 [ethoxy acrylate Phenyl ester (£02111〇1), 1^: hydrogen atom, ruler 2: extended ethyl group, R3: hydrogen atom, n=2], Aronix M-101A manufactured by Toagosei Co., Ltd. [phenol E0 modified (n = 2) Acrylate, R1: hydrogen atom, R2: ethyl group, R3: hydrogen atom, n and 2], ]\4-102 [phenolic oxime (11% 4) acrylate, 1 ^: hydrogen atom, 1^: Ethyl, R3: hydrogen atom, η and 4], Μ-110 [p-cresol phenolphthalein 0 modified (η and 1) acrylate, R1: hydrogen atom, R2: ethyl, R3: pair Indophenol, η and Lu 1], Μ-111 [n-decylphenol oxime 0 (η and 1) acrylate, R1: hydrogen atom, R2: exoethyl, R3: n-decyl, η and 1] , Μ-113 [n-decyl phenolphthalein 0 modified (η = ? 4) acrylic vinegar 'R1: complex atom, R2: extended ethyl, R3: n-decyl, η and 4] or Μ-117 [正Nonylphenol Ρ0 modified (η and 2.5) acrylate, R1: hydrogen atom, R. propyl group, R3: n-decyl group, η% 2.5], light acrylate P0 -A[C Acid phenoxyethyl ester 'R1: hydrogen atom, R2: ethyl group, R3: hydrogen atom, n=l], ❿ P-200A [the present ethoxy polyethylene glycol acetoacetate, r1: hydrogen atom, R2: exoethyl, R3: hydrogen atom, η and 2], NP-4EA [nonylphenol E0 adduct acrylate, R1: hydrogen atom, R2: extended ethyl group, R3: n-decyl group, η-4 Or ΝΡ-8ΕΑ[nonylphenol oxime 0 adduct acrylate, R1: hydrogen atom, R2: exoethyl, R3: n-decyl' η and 8] or light ester P0 [benzoic acid benzene] Oxyethyl ester, R1: methyl group, R2: propyl group, R3: hydrogen atom, n=1], BlemmerANE-300 [mercaptophenoxy polyethylene glycol acrylate] R1: hydrogen atom , R2: exoethyl, f: n-decyl, ^ and 5], ΑΝΡ-300 [壬 basic oxypolypropylene glycol acetoacetate, ri: hydrogen atom, r2: 323842 94 201233734 propyl, R3: positive Sulfhydryl, η~5], 43 ANEp_5〇〇[Mercaptophenoxy polyethylene glycol-polypropylene glycol acrylate, Ri: hydrogen atom, R2: ethyl and propyl, R3: n-decyl, # 5 + 5], 7〇ANEp_5 alkenyl. phenoxy polyethylene glycol-polypropylene glycol acrylate, Ri: hydrogen atom, R2: extension And propyl, R3: n-decyl, n_9 + 3], 75 ANEp_6 〇〇 [mercaptophenoxy polyethylene glycol-polypropylene glycol acrylate, Rl: hydrogen atom, R2: extended ethyl and extended Base, R3: n-decyl group, η#5 + 2], AAE-50 [phenoxy polyethylene glycol acrylate, Rl: hydrogen atom, R2: ethyl group, R3: hydrogen atom, η=1], _ ΑΑΕ-300 [phenoxy polyethylene glycol acrylate, Rl: hydrogen atom, R2: ethyl group, R3: hydrogen atom, π~5·5], PAE-50 [phenoxy polyethylene glycol acrylic acid Ester 'R1: methyl, R2: ethyl, R3: hydrogen atom, η=1], ρΑΕ_1〇〇 [stupoxy polyethylene glycol acrylate, Rl: methyl, R2: ethyl, R3: Hydrogen atom, n=2] or 43PAPE-600B [phenoxy polyethylene glycol-polypropylene glycol acrylate, R1: methyl, R2: ethyl and propyl, R3: hydrogen atom, n% 6 + 6 φ NK ESTER AMP-10G [Phenoxyethylene glycol acrylate (E0 lmol), R1: hydrogen atom, R2: ethyl group, R3: hydrogen atom 'n=l], AMP- 20G [phenoxyethylene glycol acrylate (E〇2mol), R1: hydrogen atom, R2: extended ethyl group, R3: hydrogen atom, η and 2], AMP-60G [ Ethoxyethylene glycol acrylate (Ε6 6 mol), R1: hydrogen atom, R2: exoethyl, R·hydrogen atom, n*6], PHE-1G [stupoxy ethylene glycol acrylate (E〇lm〇) l), R1: methyl group, R2: ethyl group, R3: hydrogen atom, n=1], Biscoat# 192 [Acrylic acid acetoacetate] R1: 氲 atom, R2: ethyl , R3: hydrogen atom, n=l], or 323842 95 201233734 _ 曰 化 SR SR - - - - - - - - - - 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- a hydrogen atom, n=l] or SR-504 [ethoxylated oxime = alkanoic acid g|, Rl: a hydrogen atom, R2: an extended ethyl group, a r3: n-decyl group) is not limited to such a compound. At the same time, two or more types may be used in combination. In the ethylenically unsaturated monomer of the formula (D6), the alkyl group of R3 has a carbon number of from 1 to 20' and is preferably from 丨 to 1 Torr. The alkyl group is not only a linear alkyl group but also a hexagram 6 group and a spinning ring. When the number of rabbits of R3 is from 丨 to 1Q, 'the base can be made into an obstacle and the resin can be prevented from approaching each other'. It promotes the adsorption/distribution of the resin pigment. If the carbon number exceeds 10, the alkyl group will be made. The steric hindrance effect becomes high, and there is even a tendency to hinder the adsorption/alignment of the benzene ring pigment. This tendency becomes apparent as the length of the carbon chain of the alkyl group of R3 becomes longer. If the carbon number exceeds 20, the adsorption/alignment of benzene %: is extremely lowered. The alkyl group having a benzene ring represented by R3 may, for example, be a benzoinyl group or a 2-phenyl(iso)propyl group. The addition of a side chain benzene ring further improves solvent affinity and pigment alignment, which not only improves dispersibility but also improves development. In the ethylenically unsaturated monomer represented by the formula (D-6), it is preferably an integer of from i to 15. When η exceeds 15, the hydrophilicity is increased to reduce the effect of the solvent, and the viscosity of the vinyl resin is increased, and the viscosity of the colored composition using the resin is increased, which may affect the fluidity. . In terms of solvent and η, η is preferably from 1 to 4. The precursor of the constituent unit (D-b2) is preferably α-mercaptostyrene, benzyl acrylate or benzyl methacrylate in terms of copolymerization with other precursors and pigment dispersibility. Or after the introduction of the benzene ring on the ethylenically unsaturated 323842 96 201233734 represented by the formula (D-6), the side chain benzene can be aggregated. And, in the case of vinegar and/or methyl propyl ketone, which kiss &lt;constituting unit (D-b3)&gt; 脂::::: There are: a pigment composition formed by a powder (6) mesh + In the hydrophobic part of the pigment or pigment and the part; in the affinity hiding, and (4) on the basis of the test liquid amount, the image 2: the total composition of the resin (D') constitutes Hn ~ light The quality or dispersion stability of the fragments. The composition _-b3) is 2 to 6 〇 wt%. If the affinity of the pigment composition formed by the material and the dispersant is insufficient (four) is insufficient, the high quality (4) light fragment cannot be obtained: the problem of deterioration of the preservation stability of the color composition will also be caused by: When part of the pattern peeling or defect exceeds 6G weight (4), it will dissolve the test image and then lengthen the development time to deteriorate the productivity of the color light-emitting sheet. The constituent unit (D_b3) has a bicyclopentane burning site material in the structure = a mesa structure, so that the molecules of the silk segment towel can be coagulated, the state &amp; steric obstacle D Λ 323842 97 201233734

(D-4)

The precursor of the structural unit (D-b3) may, for example, be an ethylenically unsaturated monomer exemplified by the following formula or ethylene and a monomer represented by the following formula (D-8). see

°-r2^QD Ο (D-7)

Formula (D-8) [In the formula (D-7) and (D-8), β _ E 7 9 -V' Q ΛΑ ^ a K broad, sub or methyl 'R2 is a breakaway 2 or 3伸 Π Π Π 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 , R丨: hydrogen atom, R2: none, m=〇] or FA_513M [dicyclopentanyl acrylate 'R1: hydrogen atom 'R2: no 'm=0], etc., but not limited to such monomers, Two or more types can also be used together. The ethylenically unsaturated monomer represented by the formula (D-8) may, for example, be Fancryl FA-511A manufactured by Sigma Chemicals Co., Ltd. [dicyclopentene acrylate], R1: hydrogen atom, R2: none, m=0. ], FA-512A [dicyclopentene oxyethyl acrylate, R1: hydrogen atom, P: exoethyl, m = 1], fa_512m [dicyclopentenyloxyethyl methacrylate, Ri: fluorenyl , R2: exoethyl, m = 1] or FA-512MT [dicyclopentenyloxyethyl decyl acrylate, Ri: methyl, R2: exoethyl, m = l], etc., but not limited These monomers may be used in combination of two or more kinds. &lt;Other constituent units&gt; • The other constituent units are constituent units other than the constituent unit (D-bl), the constituent unit (D-b2), and the constituent unit (D-b3). Other constituent unit precursors include, for example, (mercapto)methyl acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, (methyl) ) butyl acrylate, isobutyl (meth) acrylate, second butyl (meth) acrylate, tert-butyl (meth) acrylate, amyl (meth) acrylate, isoamyl (meth) acrylate , (meth)acrylic acid neopentyl ester, (mercapto) acrylic acid second pentyl vinegar, (mercapto) acrylic acid 1 methyl butyl vinegar, (meth) hexyl acrylate, (decyl) acrylic acid Ester, octyl (meth) acrylate, 323842 99 201233734 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, hexadecyl (meth) acrylate, (methyl Alkenyl (meth)acrylate such as octadecyl acrylate, isostearyl acrylate, cyclohexyl (meth) acrylate, aryl (meth) acrylate or (meth) acrylate Or aryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, (meth) acrylate 2 _ Propyl propyl ester, 10,000-carboxyethyl (meth) acrylate, bismuth polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(methyl) acrylate, triethylene glycol (Meth) acrylate, tripropylene glycol di(meth) acrylate, trimethylolpropane tris(meth) acrylate, pentaerythritol tri(meth) acrylate, hydrazine, 6-hexanediol Diglycidyl ether di(meth) acrylate, neopentyl glycol diglycidyl ether di(meth) acrylate, dipentaerythritol hexa(indenyl) acrylate, (meth) isopropyl acrylate, Various acrylates or mercapto acrylates such as ester acrylate, (meth) acrylate epoxy ester, amine ester acrylate, etc., but are not limited to these monomers, and other ethylenically unsaturated monomers may be selected according to the purpose. , or two or more types can be used together. % Other ethylenically unsaturated monomers, for example, tetrahydrofuran (meth) acrylate or acrylate having a heterocyclic substituent such as 3-mercapto oxetane (meth) acrylate; Alkoxy polyalkylene glycol (meth) acrylates such as polypropylene glycol (mercapto) acrylate or ethoxypolyethylene glycol (meth) acrylate; or (mercapto) acrylamide, N, N-dimercapto(fluorenyl) acrylamide, n,N-diethyl(fluorenyl) acrylamide, N-isopropyl (meth) acrylamide, diacetone (fluorenyl) acrylamide And acryloyl morpholine, N-hydroxydecyl (meth) acrylamide, N-vinyl decylamine or the like (fluorenyl) acrylamide or acrylonitrile. 323842 100 201233734 Meanwhile, the precursor of the constituent unit other than the above may be, for example, ethyl ethyl ether, n-propyl vinyl, iso-ethylene di-ethyl, n-butyl vinyl, isobutyl b, and Ethyl ethyl sulphate, ethylene glycol diethoxylate, neopentyl alcohol, trivinyl hydrazine, etc., ethylene or ethyl acetate acetonate or acetoacetate s s. Further, dimercapto- 2,2,-[oxybis(indenyl)]bis-2-propionic acid vinegar, diethyl-2,2'-[oxybis(methylene) can also be used. )]Bis-2-propionic acid, dicyclohexyl-2,2'-[oxybis(methylene)]bis-2-propionic acid vinegar, diphenylmethyl-2,2-[oxyl Monomer/oligomer such as bis(methylene)]bis-2-propionic acid vinegar. The above-mentioned constituent unit other than the acrylic acid-constituting unit may be used in combination with the pre-acrylic acid group-constituting unit. &lt;Importing of ethylenically unsaturated double bond&gt; Further, in order to introduce an ethylenically unsaturated monomer having an epoxy group or a method of introducing an ethylenically unsaturated double bond, An ethylenically unsaturated monomer having a warp group. Since these monomers may form constituent units other than the constituent units due to the modification of the parameters, it is expected that the weight ratio of the constituent unit (D-bl), the constituent unit (D_b2), and the constituent unit (D_b3) is finally desired. &lt;Method (Di)&gt; The method (Di) is, for example, a side chain epoxy of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having an epoxy group with one or more other ethylenically unsaturated monomers. a carboxyl group addition reaction of an unsaturated monobasic acid having an ethylenically unsaturated double bond, and a polybasic acid anhydride is reacted on the produced hydroxyl group to introduce an ethylenically unsaturated double bond to have a function as a photosensitive resin. 323842 101 201233734 and a method of introducing a thiol group having a solubility function can be introduced. The group of the unsaturated monobasic acid used in this step does not become a constituent unit (D-bl) of the resin (D_B1) but becomes another constituent unit because an ester bond is formed after an additional reaction with the epoxy group. The polybasic acid anhydride forms a carboxyl group after the reaction with the hydroxyl group, and thus can be a constituent unit (D-bl) of the resin (D_B1). Examples of the ethylarene-unsaturated double bond monomer having an epoxy group, the unsaturated monobasic acid, and the polybasic acid anhydride include, for example, the ethylenically unsaturated double bond monomer and the unsaturated monobasic acid in the fifth embodiment. The same type of ethylenically unsaturated monomer, unsaturated monobasic acid and polyacid liver. A method similar to the method (Di) is, for example, a part of a side chain carboxyl group of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having a carboxyl group with one or more other ethylenically unsaturated monomers. A method of introducing an ethylenically unsaturated double bond and a carboxyl group after an ethylenically unsaturated monomer having an epoxy group is subjected to an addition reaction. At this time, only the constituent unit corresponding to the carboxyl group which cannot be used in the addition reaction with the epoxy group is satisfied, and the constituent unit (D-bl) of the resin (D-B1) is satisfied. &lt;Method (D-ii)&gt; 'Method (D-ii) uses an ethylenically unsaturated monomer having a hydroxyl group to copolymerize with an unsaturated monobasic acid or other ethylenically unsaturated monomer having another carboxyl group. A method of reacting an isocyanate group of an ethylenically unsaturated monomer having an isocyanate group on a side chain hydroxyl group of the obtained copolymer. Examples of the ethylenically unsaturated monomer having a hydroxyl group and the ethylenically unsaturated monomer having an isocyanate group include an ethylenically unsaturated monomer having a hydroxyl group in the fifth embodiment and an ethylenic group having an isocyanate group. 323842 102 201233734 The same ethylenically unsaturated monomer having a hydroxyl group and an ethylenically unsaturated monomer having an isocyanate group. The weight average molecular weight (Mw) of the resin (D-B1) is preferably in the range of 5 〇〇〇 to 100,000, preferably in the range of 5, 〇〇〇 to 80, 000, and 5 〇〇〇 to 30,000. The scope is better. Further, the number average molecular weight (Mn) is preferably in the range of 5, 〇〇〇 to 50,000, and the value of Mw/Mn is preferably 10 or less. When the weight average molecular weight (Mw) of the resin (D_B1) exceeds 1 Torr, the viscosity of the coloring composition for the color filter becomes too large, so that it is difficult to make the interaction between the resins stronger. operating. Further, if the weight average molecular weight (Mw) is less than 5, 〇〇〇 ' may cause deterioration in visibility or adhesion to a substrate such as glass. In order to improve the film formability and the respective resistances, the content of the resin (D_B1) is preferably 3 parts by weight or more with respect to 100 parts by weight of the pigment (Al) represented by the formula (丨), thereby increasing the concentration of the colorant. In order to exhibit good color characteristics, it is preferred to use an amount of 500 parts by weight or less. It is preferably used in an amount of 50 to 25 parts by weight. • "Other resin" The coloring composition may contain a resin other than the resin (D-B1). The other resin ' is preferably a resin having a transmittance of 80% or more in the entire wavelength range of 400 to 7 Å in the visible light region, and preferably 95% or more of the resin. Other resins include a thermoplastic resin, a thermosetting resin, and a photosensitive resin. These resins may be used singly or in combination of two or more kinds. Examples of the resin include the same resins as those in the fifth embodiment. The photosensitive resin can be used in a linear polymer having a reactive group of 323842 103 201233734 such as a hydroxyl group, a carboxyl group or an amine group, and a (meth) propyl group having an isocyanate group, an aldehyde group or an epoxy group-specific substituent. The dilute acid compound or cinnamic acid reacts to introduce a photocrosslinkable group such as a (meth) acrylonitrile group or a styryl group into the resin in the linear high molecular weight. Further, a linear polymer containing an acid anhydride such as a styrene-anhydride copolymer or an α-olefin-anhydride copolymer may be used, and a (fluorenyl)acrylic compound having a hydroxyl group such as a hydroxyalkyl ester of (fluorenyl) acrylate may be used. Esterified. (Solvent) The solvent is used in order to sufficiently disperse the pigment (Α) in the binder resin (DB), and the coloring composition can be applied onto a substrate such as a glass substrate to have a dry film thickness of 0.2 to 5 cm, which is easy to form. Filter the fragments. The solvent is preferably an organic solvent. The solvent is suitably used in the same manner as in the fifth embodiment (manufacturing method of the photosensitive coloring composition). The coloring composition of the sixth embodiment can be produced by the same coloring composition as the fifth embodiment. Method of manufacture. ^ (optional component) The coloring composition of the sixth embodiment may contain a pigment dispersant (DC), a photopolymerization initiator (Dh), a sensitizer, a photopolymerizable compound, and a thiol Any component such as a UV absorber, a polymerization inhibitor, a storage stabilizer, or other additives. Specific examples of such arbitrary components are the same as in the fifth embodiment. Further, suitable examples, suitable usage amounts, and the like are also the same as in the embodiment. (Removal of coarse particles) The coloring composition of the sixth embodiment is also the same as the coloring of the third embodiment 323842 104 201233734, and it is preferable to remove coarse particles. [Solvent, optional component] Hereinafter, specific examples of the solvent and optional components used in the coloring composition for a color filter described above will be described. (Other coloring agents (other pigments)) Other coloring agents (other pigments) used in the coloring composition include, for example, CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12 , 14, 15, 16, 17, 2, 22, 23, 3, 32, 37, 38, 4, 47, 48, ® 48: Bu 48: 2, 48: 3, 48: 4, 49, 49: 49 : 2, 50 : 1, 52 : Bu 52 : 2 , 53 , 53 : Bu 53 : 2 , 53 : 3 , 57 , 57 : Bu 57 : 2 , 58 : 4 , 60 , 63 , 63 : Bu 63 : 2, 64, 64: Bu 68, 69, 8 Bu 81: Bu 81: 2, 81: 3, 81: 4, 83, 88, 90: 1, 1 (H, 101: Bu 104, 108, 108: Bu 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, φ 184 , 185 , 187 , 188 , 190 , 192 , 193 , 194 , 200 , 202 , 206 , 207 , 208 , 209 , 210 , 214 , 215 , 216 , 217 , 220 , 22 , 223 , 224 , 226 , 227 , 228 , 240, 230, 231, 232, 233 , 235 , 236 , 237 , 238 , 239 , 242 , 243 , 245 , 246 , 247 , 249 , 250 , 251 , 253 , 254 , 255 , 264 , 255 , 256 , 257 , 258 , 259 , 260 , 262 , 263 , 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286 or 287 Pigment. The red pigment may be, for example, xanthene, monocouple 323842 105 201233734 nitrogen (beta ketone, barbituric acid, metal complex, etc.), diazo , 蒽醌, etc. Specific examples thereof include salt-forming compounds such as C. I. acid red 52, 87, 92, 289, and 338, which are acid dyes of xanthene-based acid dyes. These pigments may be used singly or in combination of two or more. For example, CI Pigment Orange 1, 2, 5, 13, 16, 17, 19, 20, 2, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 51, 55 may be used in combination. 59, 6 Bu 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78 or 79 and other orange pigments and / or CI pigment yellow 1, Φ 1: Bu 2 3, 4, 5, 6, 9, 10, 12, 13, 14, 15, 16, 17, 18, 24, 3, 32, 34, 35, 35: Bu 36, 36: Bu 37, 37: Bu 40 4, 42, 43, 48, 53, 55, 60, 6 and 62, 62: 1, 63, 65, 73, 74, 75, 77, 8 and 83, 87, 93, 94, 95, 97, 98 , 100, 1 (Π, 104, 105, 106, 108, 109, 110, 1U, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 127: 128, 129, 133, 134, 136, 138, 139, 142, 147, • 148, 150, 15 152, 153, 154, 155, 156, 157, 158, 159, 160, 16 162, 163, 164, 165, 166 , 167, 168, 169, 170, 17 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 183, 184, 185, 18 7, 188, 189, 190, 19 191: 1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208, 213, 214, a yellow pigment such as 218, 219, 220 or 221. Further, examples of the orange dye and/or the yellow dye include a quinoline type, a monoazo type (pyridone type, a barbituric acid type, a metal complex type, etc.). Diazo, methine, etc. 323842 106 201233734 These pigments may be used singly or in combination of two or more. Among these pigments, suitable coloring agents are exemplified by hydrazine. Anthraquinone pigment, monoazo, diazo or xanthene dye, etc. In terms of brightness and contrast, specifically, it is preferably CI Pigment Red 48: 1, 122, 168, 176, 177, 185, 202 , 206, 207, 209, 224, 242, 254, CI Pigment Orange 38, 7 Bu CI Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180, 185 and CI Acid Red 52 Compound. Further, c. 丨. Pigment Red 177, 209, 224, 242 or 254; C. I. Pigment Yellow Ring 83, 138, 139, 15 ◦ or 180 is more preferable. (Organic solvent) Examples of the organic solvent used in the coloring composition include ethyl lactate, stupid methanol, 1,2,3-trichloropropane, 1,3-butanediol, and 1,3-butanediol. , 3-butanediol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3, 5, 5-trimethyl-2-cyclohexanyl- 1-ketone, 3, 5, 5-tridecylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-i, 3-butanediol, 3-methoxy-3-methyl Base 1-butanol, 3-decyloxy-3-mercaptobutyl acetate, 3-decyloxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-nonylbenzene, -diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, ν, Ν-dimethylformamide, n-butanol, n-butylbenzene, n-propyl acetate, Ν-甲Pyrrolidone, o-diphenylbenzene, o-gas toluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethyl stupid, t-butylbenzene, tert-butyl Benzene, butyrolactone, isobutanol, isoindolinone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl hydrazine, ethylene glycol monoacetic acid acetate, Ethylene glycol single third Ding Jun, ethylene glycol Monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene 323842 107 201233734 monool early chlorinated I, ethyl phthalate 留 乙 乙 知 早 early methyl ether, ethylene glycol monoterpene ether acetate , diiso-1_, diethylene glycol diethyl ether, diethylene glycol, ethylene glycol monoethylene glycol, diethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, -ethyl one, one B1, Yiyi, early methyl ether, cyclohexanol, cyclohexanol acetate, ketone, dipropylene, brewing

K mouth is known as monomethyl ether, dipropylene glycol monomethyl ether acetate, propylene glycol::: ethylene dipropylene glycol monotop, dipropylene glycol monopropyl ether, two early (four), - acetol, triacetin §, tripropylene glycol monobutyl Glycol singly, propylene glycol monodiacetate®, propylene glycol benzoquinone, alcohol monobutyl sulphate, propylene glycol monoethyl acetate vinegar, propylene glycol monobutyl hydrazine, propylene glycol monopropyl ether, propylene glycol monomethyl hydrazine, propylene glycol monomethyl ether acetate vinegar , propylene glycol, early oxime ether propionic acid vinegar, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, acetic acid 戍 1、 1, 1, acetic acid, butyl, acetaminophen, acetic acid, acetaminophen曰, Second Reading®, etc. These solvents may be used singly or in combination of two or more kinds at any ratio as necessary. Among them, in terms of good dispersibility, permeability, and coating of the coloring composition, it is preferable to use lactic acid ethyl lactic acid (IV), propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and ethylene glycol monoterpene. A diol acetate such as ether acetate or ethyl alcohol monoethyl ether acetate; an alcohol such as benzyl alcohol or diacetone alcohol or a ketone such as cyclohexanone. (Resin type dispersant) The resin type dispersant has a pigment affinity portion capable of adsorbing on a colorant and a portion having compatibility with a color carrier, and functions as a stable dispersion after being adsorbed on the colorant. A component on a colorant carrier of a colorant. The resin type dispersant may specifically be a polycarboxylate, a polyacrylic acid 323842 108 201233734, a polycarboxylic acid vinegar, an unsaturated polyamine, a poly-acid, a poly-acid (partial) amine salt, a polycarboxylate ammonium salt, a poly a carboxylic acid alkylamine salt, a polyoxyalkylene oxide, a long-chain polyamine guanamine compound, a trans-containing polycarboxylate or a modified substance thereof, a poly(lower alkylene imine), and a free carboxyl group An oily dispersant such as guanamine or a salt thereof formed by the reaction of a polyester, (mercapto)acrylic acid-styrene copolymer, (mercapto)acrylic acid-(meth)acrylate copolymer, styrene-maleic acid Water-soluble resin or water-soluble polymer compound such as copolymer, polyvinyl alcohol or polyvinylpyrrolidone, polyester-based, modified polypropionate-based, epoxidized/epoxypropane® addition compound, and phosphate ester system Wait. Although these dispersing agents may be used singly or in combination of two or more kinds, they are not necessarily limited to these compounds. Commercially available resin-type dispersing agents include Disperbyk-101, 103, 107, 108, 110, 111, 112, 116, 130, 140, 142, 154, 161, 162, 163, 164, which are manufactured by BYK Chemie Japan Co., Ltd. 165, 166, 167, 168, 170, 17 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2009, 2010, 2020, 2025, 2050, 2070, 2095, 2150, 2155, 2163, 2164 or Anti-Terra-U, 203, 204; or BYK-P104, P104S, 220S, 6919, 21116, 21324, 21407, 21715, etc. or Lactimon, Lactimon-WS or Bykumen, etc.; SOLSPERSE-made by Lubrizol, Japan 3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 56000, 76500, etc.; EFKA-46, 47, 323842 109 201233734 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, manufactured by Ciba Japan Co., Ltd. 4055, 4060, 4080, 4400, 44 (Π, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 45, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc.; DISPARLON 3600Ν, DISPARLON 1850 made by Nanben Chemical Co., Ltd.; Ajisper-PAm, PB7U, PB82, PB822, PB824, etc. manufactured by Ajinomoto FineTech Co., Ltd. Used alone or in combination of two or more. ® Among these products, Disperbyk-108, 110, 11, 112, 116, 142, 180, 2000, 2001, manufactured by BYK Chemie Japan Co., Ltd., which is a resin-based pigment dispersant having an acidic functional group, or Lubrizol, Japan SOLKAPER-3000, 21000, 26000, 36600, 41000 or EFKA-4401, 4550 manufactured by Ciba, or DISPARLON 3600N, DISPARLON 1850, or Ajisper-PAlll manufactured by Ajinomoto FineTech Co., Ltd., but Not limited to such products. φ (surfactant) The surfactant may, for example, be sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, an alkali salt of a styrene-acrylic acid copolymer, sodium stearate, Sodium alkylnaphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanol of dodecyl sulfate, triethanolammonium dodecyl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer Anionic surfactant such as polyoxyethylene ether ether sulphonate; polyoxyethylene oleyl ether, polyoxyethylene decyl ruthenium, polyoxyethylene phenyl hydrazine, polyoxyethylene oxime ether Acid ester, polyoxyethylene sorbitan monostearate, polyethylene glycol monododecanoate, etc. 323842 110 201233734 Nonionic surfactant; burnt base four-salt salt or such epoxy a cationic surfactant such as an adduct; an amphoteric surfactant such as an alkylbetaine or an alkylimidazoline such as an alkyldidecylaminoacetate betaine. The surfactant may be used singly or in combination of two or more kinds, but it is not necessarily limited to such a surfactant. (Photopolymerizable monomer (photopolymerizable compound)) A monomer or oligomer which can be cured by ultraviolet light or heat to form a transparent resin, for example, (mercapto)methyl acrylate or (mercapto)acrylic acid Ethyl ester, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, carboxyethyl (meth) acrylate, polyethylene glycol bis (曱) Acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol bis(indenyl)acrylate, tripropylene glycol bis(indenyl)acrylic acid vinegar, tri-propyl mercaptopropane tris(曱) Acrylate, neopentyl alcohol tri(meth) acrylate, 1,6-hexanediol diglycidyl ether bis(indenyl) acrylate, bis-A diglycidyl ether bis(indenyl) acrylate , neopentyl glycol dihydrate # glyceryl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate vinegar, dipentaerythritol penta(meth)acrylate, (meth)acrylic acid癸 vinegar, vinegar acrylate, hydroxylated melamine (mercapto) acrylate, ( Various acrylates and mercaptoacrylates such as methyl acrylate epoxy esters and amine ester acrylates, (mercapto) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, Pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxyindenyl (decyl) acrylamide, N-vinylformamide, propionitrile, etc. 'but not necessarily limited to these compounds. These photopolymerizable compounds can be used alone or in combination of two or more kinds at any ratio as necessary. 323842 111 201233734 (Photopolymerization initiator) Photopolymerization initiator can be used 4-phenyl oxydichloro benzene benzene, 4-tert-butyl-dichloro ethane benzene, diethyl acetophenone benzene, 1 _ (4 -isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2 fluorenyl μ-ι^-(methylthio) benzyl]_2 -Mallin-propanone-oxime, 2-(dimethylamino)-2-[4-(nonylphenyl)indolyl]-bu [4-(4-morpholinyl)phenyl]-1- Butyl ketone compounds such as butanone or 2-benzyl-2-didecylamino-1-(4-morphinylphenyl)-butan-1-one; benzoin, benzoin methyl ether, benzoin ethyl ether, A benzoin compound such as benzoin or benzoin dimethyl ketal, benzophenone, benzoylbenzoic acid, benzoyl benzoyl phthalate, 4-phenyl benzophenone, Dibenzophenone, acrylated benzophenone, 4-phenylmercapto-4,-methyldiphenyl sulfide or 3,3',4,4'-tetra (t-butylperoxycarbonyl) Dibenzophenones such as diterpenoids; thioxanthone, 2-oxothione, 2-mercaptothioxanthone, isopropylthioxanthone, 2,4-diisopropyl Ketoxone Or a thioxanthone compound such as 2,4-diethylthioxanthone; 2, 4, 6-three • gas-s-three tillage, 2-phenyl-4,6-bis(trichloromethyl)- S-trimorphine, 2-(p-methoxyphenyl)-4,6-bis(trichloroindenyl)-s-trin, 2-(p-indolephenyl)-4,6-bis ( Trichloroindolyl)-s-three-plowing, 2-piperidin-4,6-bis(trioxanyl)-3-trinomethane, 2,4-bis(tris-methyl)-6-styryl -3-three tillage, 2-(naphthylfluorenyl-1-yl)-4,6-bis(trichloromethyl)-s_three tillage, 2-(4-methoxynaphthylquinone-I-group )-4,6-bis(trismethyl)-s-triterpene, 2,4-trichloromethyl-(piperidinyl)-6-three tillage or 2,4-trichloroindolyl-(4, 3-trimyl compound such as -methoxystyryl-6-trientin; ethyl ketone, 1-[9-ethyl-6-(2-methylphenylhydrazino)-9H-isoxazolyl-3- Base]-, 1-(〇-acetamidine), 1,2-octanedione, 1-323842 112 201233734 [4-(phenylthio)-, 2-(0-benzamide)] or; 2-(Ethyl)-N-(l-phenyl-2-oxo-2-(4'-methoxy-naphthyl)ethylidene) hydroxyamine and other oxime ester compounds; 4,6-trimercaptobenzylidene)phenylphosphine oxide or 2,4,6-trimercaptobenzamide Diphenylphosphine oxide, etc.; 9,10-phenanthrenequinone, anthracene, ethylhydrazine or the like anthraquinone compound; a borate ester compound; an oxazole compound; an oxime compound; or a titanocene ) a compound or the like. These photopolymerization initiators can be used in combination of two or more kinds at any ratio using one kind or combination. Among these compounds, at least one or more photopolymerization initiators containing a group selected from the group consisting of an acetophenone-based compound, a phosphine-based compound, an amino-salt compound, and a diester-based compound are preferably used as the light. Polymerization initiator. Also, since these photopolymerization initiators are contained, the pattern shape and linearity of the filter segments can be made better. (sensitizer) The sensitizer may, for example, be a chalcone derivative or a second stupid

A 1,2-dione derivative represented by acetone (dibenzoylacetone), which is represented by unsaturated steroids, camphorquinone, etc.

Aroma derivatives, anthraquinone derivatives, naphthoquinone derivatives, anthracene derivatives, derivatives, thioxanthene derivatives, xanthone derivatives, sinone derivatives, coumarin derivatives, ketones Bean derivatives, cyanine derivatives, melocyanine derivatives, oxyphthalocyanine (polymethine pigments such as οχοη〇ι derivatives, acridine derivatives, scorpion derivatives) , thiazolidine derivatives, sorghum derivatives, porphyrin derivatives, azulene derivatives, azulenium derivatives, squarylium 323842 113 201233734 (squarylium) derivatives, porphyrin Derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzidine derivatives, tetraterpene oxime σ 丫哄 derivatives, eucalyptus derivatives, tetragas 〇 丫哄 α丫哄(tetraazaporphirazine) derivative, tetraterpenoid derivative, naphthalocyanine derivative, hypophthalocyanine derivative, π-pyranium derivative, sulfur-based rust derivative, four-leaf Tetraphylline derivatives, annulene derivatives , a helical beta-pyran derivative, a helically-purine derivative, a sulfur-based helical 11-pyran derivative, a metal aromatic vinegar complex, a conjugated product, or a Michelle ketone Derivatives, hydrazine pi-salt derivatives, α-decyloxyesters, mercaptophosphine oxides, mercaptophenyl chain acetic acid, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethylhydrazine, 4 , 4'-diethyl isosaccharide (^8〇0111:1131〇?1^11〇116), 3,3' or 4,4'-tetra(t-butylperoxycarbonyl)benzophenone And 4, 4'-diethylaminobenzophenone, etc., if necessary, two or more types of sensitizers are used in an arbitrary ratio. More specifically, the "Pigment Handbook" φ (produced by Ohara Shinto et al.) The sensitizer described in "Special Functional Materials" (1986, CMC), edited by "The Chemistry of Functional Pigments" (CMC, 1981, MIT, 1986) However, it is not limited to these compounds. Further, other sensitizers which exhibit light absorption from the ultraviolet to near-infrared region may be contained. (Polyfunctional thiols) Polyfunctional thiols may be used. Examples are hexanedithiol, decanedithiol, 1,4-butanediol dithiopropionate, 1,4-butanediol dithioglyceride, ethylene glycol dithioglyceride, Ethylene glycol dithiopropionate, trishydroxypropylpropane triglyceride 323842 114 201233734 thioglycerate glycerin, succinyl propyl trithiopropionate, three &quot; Acid from the purpose), Sanshenji three (3) thiol butyrate vinegar), methyl group tris(3-thiol propionate), neosodium thioglycolate S曰, neodymidine Sodium thiopropionate, neodymium oxime (3_thiol propionate), dipentaerythritol (3-thiol propionate), trithiol propionate ((1)ylethyl) Cyanuric acid vinegar, 1,4-diyl mercaptan benzene, 2,4,6-trithiol-based soil, 2-(Ν'Ν-dibutylamino)_4,6-dithiol _s_三哄 and so on. Such

Multifunctional thiols can be used alone! If necessary, mix 2 or more at any ratio and use it. (Ultraviolet absorber) The ultraviolet absorber may, for example, be 2-[4_[(2_hydroxy_3_(dodecane and dodecyl)oxypropyl)oxy]_2-hydroxyphenyl]_4, 6 - bis(2'4-dimethylphenyl)-1,3,5-trimorphine, 2-(2-hydroxy-4-yl-[1-octyloxycarbonylethoxy]phenyl)-4,6- Bis(4-phenylphenyl)-indole, 3, 5_three tillage and other hydroxyphenyl triterpenoids; 2-(5-fluorenyl-2-hydroxyphenyl)benzotriazole, 2-(2H- Benzyldiazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl) monophenol, 2-(3-tert-butyl-5-fluorenyl-2-hydroxyl Phenyl)-5-gas benzotriazole and other diterpenoids, 2, 4-diphenyl benzoquinone _, 2-mono-based -4-xyoctyl phthalone, 2, 2', 4 , 4' _ tetrahydroxybenzoedione and other benzodiazepines; phenyl lauric acid vinegar, p-t-butylphenyl lauric acid vinegar and other vinegar vinegar; ethyl 2 - cyano-3, 3 _ — base acrylic vinegar and other aromatic acetonic acid; 2, 2, 6, 6-tetramethylene piperidin-1-yl (triacetone-aminooxy), double (2, 2, 6, 6-tetramethyl-4-piperidinyl)-sebacate, polytetrabutyl)amino]-1,3, 5-trinyl-2,4-diyl][(2, 2 , 6, 6- Yue-4-piperidinyl 323 842 115 201 233 734 yl) amino] hindered amine and the like. These ultraviolet absorbers can be used singly or in combination of two or more kinds at any ratio as necessary. (Polymering agent is prohibited) The polymerization inhibitor is exemplified by, for example, methylhydroquinone, tert-butylhydroquinone, 2,5-di-tert-butylhydrogen, 4-benzene-branched, 4-methoxyl, 4 -Methoxy-1-naphthoquinone, tributyl catechin derivatives and compounds; morphine, bis-(1-dimethylbenzyl) thiophene, 3, 7-dioctine Amine compounds such as phenylethione; copper dibutyldithiocarbamate, copper diethyldithiocarbamate, manganese diethyldithiocarbamate, manganese diphenyldithiocarbamate And other nitroso compounds such as copper and manganese salt compounds, 4-arylene, N-arylene diphenylamine, N-nitrosocyclohexylhydroxylamine, N-nitrosophenylhydroxylamine, and the like Ammonium or aluminum salts, etc. These non-polymerization agents may be used singly or in combination of two or more kinds in any ratio if necessary. (Antioxidant) The "antioxidant" may be a compound having a function of absorbing ultraviolet light, supplementing the function of a radical, or decomposing a peroxide. Specifically, a hindered phenol system, a hindered amine system, a phosphorus system, or a sulfur may be used. As the antioxidant, a known ultraviolet absorber, an antioxidant, or the like can be used as the antioxidant of the compound of the trimethoprim type, the benzophenone type, the hydroxylamine type, the salicylate type, and the tri-till type. This specific antioxidant can be used alone or in combination of two or more kinds at any ratio if necessary. In view of the transmittance and sensitivity of the coating film, the antioxidants are preferably hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants or sulfur-based antioxidants. At the same time, it is preferably a hindered phenol-based antioxidant, a 323842 116 201233734 hindered amine-based antioxidant or a phosphorus-based antioxidant. (Amine compound) ▲ The amine compound may, for example, be triethanolamine, methyldiethanolamine, triisopropanolamine, 4-didecylaminobenzoic acid methyl vinegar or 4-dimethylamino benzoic acid acetamidine 4-methylaminobenzoquinone warm isoamyl, 2-dimethylaminobenzoic acid ethyl acetophenone, 4-nonylaminobenzoic acid 2_-ethylhexyl ester and N,N-dimercaptopurine Aniline and the like. These amine compounds may be used singly or in combination of two or more kinds in any ratio as necessary. • (Leveling agent) The leveling agent should preferably be a dimethyl polyoxo-oxygenate having a polyether structure or a polyester structure in the main chain. A specific example of dimethyl polychlorite with a polyphonic structure in the main chain is exemplified by FZ-2122 manufactured by Toray ray d〇wc〇rning and BYK_333 manufactured by BYK Chemie. Wait. On the main chain

Specific examples of the polyfluorene-based polyfluorene-oxygen grouping can be exemplified as MK.

BYK_310, BYK-370, etc. manufactured by Chemie. It is also possible to use a dimethyl (tetra)oxy group having a _ structure in the main chain and a dimethyl polyoxyalkylene having a polyacetate structure in the main chain. As a particularly preferred leveling agent, one of all surfactants having a hydrophobic group and a hydrophilic group in the molecule can be used, and even if it does not have a hydrophilic group, it is small in water/complexity, and is added to the coloring composition. It can have a characteristic that its surface tension energy is low, and it has good wettability to the glass substrate regardless of whether the surface tension energy is low or not, and it is preferable to use it to sufficiently suppress the addition amount of the coating film which is not caused by the occurrence of foaming. An electrostatic leveling agent. For the leveling agent having such good characteristics, it is preferred to use dimethyl 323842 117 201233734-based polyoxyalkylene having a polyalkyl oxide unit. As a polycycloolefin oxide unit, a polysiloxane oxide unit, a dimethyl polyoxa oxide, an oxide monoethylene oxide unit and a polypropylene oxide mono τ have a poly-polycyclic ortho-organized unit The polymorphism with the diterpene group may be a combination of the polycycloolefin oxide unit on the _, , σ σ-shaped nr-based polyfluorene-repeating soap element, combined with the diterpene group (four) At the end of the end of the end, the type of the straight-chain W-type which is recombined with the dimethoate. A dimercapto (four) nucleus with polycycloolefin oxide single 7G, which has been manufactured by Dongcai Materials Co., Ltd., such as FZ-211G, FZ-2122, FZ-2130, FZ_2166, fz_2191, FZ-2203, FZ- 22G7 'but not limited to other products. One type of the leveling agent may be used singly. When necessary, two or more types may be used in combination at any ratio. In the leveling agent, an anionic, cationic, nonionic or amphoteric surfactant may also be added. The surfactant may be used in combination of two or more kinds. The anionic surfactant which can be added to the leveling agent can be supplemented, for example, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, alkylnaphthalenesulfonic acid Sodium, sodium alkyl diphenyl ether disulfonate, dodecyl sulfate monoethanolamine, dodecyl sulfate triethanolamine, dodecyl ammonium sulfate, stearic acid monoethanolamine, sodium stearate, eleven alkyl Sodium sulfate, styrene-acrylic acid copolymer monoethanolamine, polyoxyethylene alkyl ether phosphate, and the like. The cationic surfactant which can be added to the leveling agent can be supplemented, for example, an alkyl quaternary ammonium salt or an ethylene oxide adduct thereof. The nonionic surfactant which can be added to the leveling agent can be supplemented, for example, polyoxyethylene alkane 323842 118 201233734 oil ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene ether ether Sulphate, polyoxyethylene sorbitan monostearate, polyoxyethylene glycerol, single siu vinegar, etc.; for example, alkyl dimethylamino acetic acid betaine, alkyl imidazoline amphoteric interfacial activity A surfactant or the like, and a surfactant of a fluorine- or anthrone. (hardener, hardening accelerator) As a curing agent, a phenolic resin, an amine compound, an acid anhydride, an active g, a sulphate compound, a sulfonic acid compound, etc. are effective, but it is not limited to these compounds. The product obtained by the reaction with the thermosetting resin can be used as a curing agent. Further, among these curing agents, a compound having two or more phenolic hydroxyl groups and an amine curing agent in one molecule is preferable. As the hardening accelerator, for example, an amine compound (for example, dicyandiamide, benzoguanidinylamine, 4-(dimethylamino)-N,N-dimercaptobenzylamine, 4 can be used. - alkoxy-n,N-dimercaptobenzamine, 4-mercapto-N,N-dimercaptobenzamine, etc.), quaternary ammonium salt (for example, triethylphenylhydrazine chloride Ammonium, etc.), • Block isocyanate compounds (eg, dimethylamine, etc.), imidazole derivatives, bicyclic guanidine compounds, and salts thereof (eg, imidazole, 2-mercaptoimidazole, 2-ethylimidazole, 2- Ethyl-4-mercaptoimidazole, 2-phenylimidazole, 4-phenylimidazole, cyanoethyl-2-phenylimidazole, i-(2-cyanoethyl)-2-ethyl-4 - mercapto imidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), guanamine compounds (eg, melamine, amide, acetaminophen, present dihydrate, etc.), S-three π well derivative (for example, 2, 4-diaminomethyl methacrylamidooxyethyl-S-trimorphine, 2-vinyl-2,4-diaminotriazine, 2-vinyl) 4, 6-diamino _s_three tillage / cyanuric acid adduct, 2, 4-diamino-6- 323842 119 20123 3734 mercapto acrylamide ethoxyethyl-s-three tillage / cyanuric acid adduct, etc.). These hardening accelerators may be used alone or in combination of two or more. (Storage stabilizer) The storage stabilizer may, for example, be 2,6-bis(1,1-didecylethyl)-4-nonylphenol, neopentyl quinone [3-(3,5-di- Tributyl-4-hydroxyphenyl)propionate], 2,4-bis-(n-octylthio)-6-(4-hydroxy-3, 5-di-t-butylaniline)-1 , 3,5-three tillage, third butyl. Hindered phenols such as catechol; organophosphines such as tetraethylphosphine, triethylphosphine, tetraphenylphosphine; dimercapto® dithiophosphoric acid, dipropyl dithiophosphoric acid, dibutyl a phosphite such as molybdenum dithiophosphate; a sulfur system such as dodecyl sulfide or benzoquinone; a quaternary amine chloride such as phenylmercaptotriyl chloride or diethylhydroxylamine; lactic acid or oxalic acid Such as organic acids and their methyl ethers. These storage stabilizers may be used singly or in combination of two or more kinds at any ratio if necessary. (Adhesive Lifting Agent) Examples of the adhesion promoting agent include vinyl decanes such as ethylene ginate (/5-decyloxyethoxy) 矽 φ alkane, vinyl ethoxy decane, and vinyl trioxoxane; T- Mercapto propylene oxy propylene trioxane oxane (mercapto) propylene decane; p-(3, 4-epoxycyclohexyl)ethyltrimethoxy decane, lutene (3,4-epoxy ring) Hexyl)methyltrioxoxane, p-(3,4-epoxycyclohexyl)ethyltriethoxydecane, lu-(3,4-epoxycyclohexyl)decyltriethoxydecane, T - an epoxy decane such as glycidyl oxypropyl oxoxane; an epoxy decane such as 7-glycidoxypropyl ethoxy hydride; N-; 8-(aminoethyl)r-aminopropyltrimethoxy decane , N-yS-(Aminoethyl)T-aminopropyltriethoxyoxane, N-/3-(Aminoethyl)t-aminopropylmercaptodiethoxyoxane, r-323842 120 201233734 Aminopropyl triethoxy decane, aminopropyl trimethoxy decane, N-phenyl-r-aminopropyl trioxoxane, fluorenyl-phenyl-r-aminopropyl triethoxy decane, etc. Amino decanes; r-thiol propyl trioxane, r-thiol propyl triethoxy hydrazine a decane coupling agent such as a thiodecane such as an alkane. These adhesion enhancers may be used singly or in combination of two or more kinds at any ratio if necessary. [Color Filter] A color filter according to the seventh embodiment will be described. [Seventh embodiment] (Color filter) The color filter of the seventh embodiment is formed by using the coloring composition for a color filter described above. According to the seventh embodiment, a high-definition color filter excellent in luminance and contrast ratio can be provided. The color filter of the seventh embodiment can be used for a color liquid crystal display, a color photographic tube element, or the like. The color filter has a red filter segment, a green filter segment, and a blue φ filter segment. The red filter segment is formed by the coloring composition described above. Further, the color filter may also have a magenta filter segment, a cyan (cyano) filter segment, and a yellow filter segment. The color filter generally has the above-described filter segments on a transparent substrate. The transparent substrate may be a glass plate such as soda lime glass, low alkali borosilicate glass or alkali-free aluminum boron borosilicate glass, or a resin plate such as polycarbonate, polymethyl methacrylate or polyethylene terephthalate. . Further, a transparent electrode made of indium oxide, tin oxide or the like may be formed on the surface of the glass plate or the resin skin to be used for liquid crystal driving after flattening. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. When the coating film is dried, a vacuum dryer, a convection oven, an IR oven, a heating plate, or the like can also be used. The green filter fragments can be formed using a generally green coloring composition comprising a green pigment and a colorant carrier. As the green pigment, for example, C.I. Pigment Green 7, 7, 36, 37, and 58 can be used. Further, a yellow pigment or a yellow dye may be used in combination with the green coloring composition. The yellow pigments which can be used together are, for example, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 3, 32, 34, 35, 35 : 1, 36, 36 : Bu 37, 37 : 1, 40, 42, 43, 53, 55, 60, 6 Bu 62, 63, 65, 73, 74, 77, 8 Bu 83, 93, 94, 95 , 97, 98, 100, 1 (U, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139 , 147, 150, 15 152, 153, 154, 155, 156, 16 162, 164, 166, 167, 168, 169, 170, 17 172, 173, 174, 175, 176, 177, 179, 180 , yellow pigment such as 18 182, 185, 187, 188, 193, 194, 198, 199, 213, 214, 218, 219, 220 or 221. Further, a yellow dye which can be used in combination, for example, 啥琳系,单单An azo system (an acetophenone system, a barbituric acid system, a metal complex system, etc.), a diazo system, a sulfhydryl group, etc. A blue filter component can be used with a blue pigment and a colorant carrier. General blue coloring Formed as a composition. For blue pigment, for example, c. I. Pigment Blue 15, 15 : Bu 15 : 2, 15 : 3, 15 : 4, 15 : 6, 16, 22, 60, 64, etc. The purple pigment can also be used in combination with the coloring composition. The purple pigment which can be used in combination with 323842 122 201233734 can be listed as CI pigment purple 1, 19, 23, 27, 29, e 乂 2 grid 37, 4°, 42, 5 〇 and other purple pigments. Also 'can be used to show the ^ or i color test _, acid dye salt compound. When using = section, in terms of heat resistance and brightness, it should be (4) dye. Method for manufacturing light sheet) The color filter can be produced by a printing method or a photo-etching lithography method. When the filter is formed by a brush method, the pattern can be repeatedly printed and dried by using the preparation as a printing oil. Therefore, it is a manufacturing method of a color filter, which is excellent in low cost and high in mass productivity, and is a composition which is dried and solidified by a pattern printing and a fine cloth having a smoothness during printing. The fluidity of the plate or ink can also be adjusted. It is also expected to control the oil on the printing machine. When the above-mentioned solvent development type or inspection image type = light segment, the preparation may be performed on a transparent substrate, and the coating method such as coating method or affinity coating method may be applied to the soil plate to make it dry. The thickness is from 2 to 5. If necessary, in the dry state, the contact state is set to have a pre-transmission with the lining or to remove the uncured portion to form the desired repetitive operation of the developer. Light film. Also, it must be 3: = heating: promoting the polymerization of the colored resist material. The borrowing technology method can produce a color film with higher precision than the above printing method. 323842 123 201233734 Then, the filter &amp; can be formed by dipping in a solution, or by removing the uncured portion of the liquid to form a desired pattern. Heating may be applied as necessary to promote polymerization of the filter segments formed by the development. By the optical lithography technique, it is possible to manufacture a filter segment having a higher precision than the above printing method. At the time of development, an aqueous solution of sodium carbonate or sodium hydroxide can be used as the alkali developing solution, and an organic base such as dimethylbenzamide or triethanolamine can also be used. Further, an antifoaming agent or a surfactant may be added to the developing solution. As a method of image processing, a shower development method, a spray development method, a dipping development method, a liquid coating (pudd 1 e) development method, or the like can be applied. Further, in order to increase the ultraviolet exposure sensitivity, after the above-mentioned enamel resist honey cloth is dried, it may be coated with a water-soluble or alkali water-soluble resin (for example, polyvinyl alcohol or water-soluble acrylic resin) to form an oxygen-preventing agent. After the film that hinders the polymerization is exposed, ultraviolet exposure is performed. The color filter can be produced by an electroforming method other than the above method, a transfer method, or the like, and any of the above-described coloring composition or photosensitive coloring composition can be used. Further, the electrophoresis method is a method of producing a color filter by electrophoresing a colloidal particle on a transparent conductive film to form a filter segment of each color by electrophoresis of a colloidal particle. Further, the transfer method is a method in which a filter segment is formed on the surface of a peelable transfer substrate in advance, and the light-receiving segment is transferred onto a desired substrate. The coloring composition described above can be used in any method, but in particular, the compositions of the fifth and sixth embodiments are most suitable for photolithography. Before forming a filter segment of each color on the transparent substrate or the reflective substrate, a black matrix may be formed in advance by 323^42 124 201233734. As the black matrix, a multilayer film of chromium or chromium/chromium oxide, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed can be used, but it is not limited to these films. Further, a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then filter segments of respective colors may be formed. Further, on the color filter, a protective film, a transparent conductive film, a columnar spacer, a liquid crystal alignment film, or the like can be formed as necessary. The color glazing sheet can be bonded to the substrate by using a sealant, and the liquid crystal is injected from the injection port provided in the sealing portion, and the injection port is sealed. If necessary, the polarizing film or the retardation film is attached to the outside of the substrate. After that, a liquid crystal display is manufactured. Such a liquid crystal display can be used for color filtering using twisted nematic (TN), super twisted nematic (STN), in-plane switching (ips), vertical orientation (VA), optically compensated bending (〇CB), and the like. In the liquid crystal display mode in which the light is colored. [Examples]

Although the embodiments of the present invention are described on the basis of the embodiments, the present invention is not limited to the scope. In the case of the "Example A] and the use of the limit of "Special", "Parts" and "%" indicate "Quality Quality / 0". In the case of producing a pigment composition or a coloring composition, it is a derivative. (average primary particle size of pigment) ··α·~3) of the two-grain scale and the touch substance, the benzo-2 of the formula (7-1), the organism of the formula (8~5) And the ketone of the formula (14-1) 323842 125 201233734 The average primary particle diameter of the produced pigment composition was measured (calculated) by the following method. The average primary particle diameter of the pigment was a transmission type (TEM) electron microscope. The method of directly measuring the size of the primary particle diameter by electron micrograph is specifically measured, and after measuring the short axis diameter and the major axis diameter of the primary particles of each pigment, the average is used as the average primary particle diameter of the pigment. Next, for 100 or more pigment particles, the volume (weight) of each particle is determined by a cube approximate to the obtained particle diameter, and the volume average particle diameter is taken as the average primary particle diameter. ® (mass average molecular weight of the binder resin) The mass average molecular weight of the acrylic resin is measured by the method described below. The mass average molecular weight (Mw) of the acrylic resin is a GPC (manufactured by Tosoh Corporation) equipped with a TSKgel column (manufactured by Tosoh Corporation) and equipped with an RI detector. HLC-8120GPC) determination The developing solvent is a mass average molecular weight (Mw) converted to polystyrene using THF. φ First, the diketopyrrolopyrrole pigment and the diketopyrrolopyrrole pigment composition used in the examples and the reference examples will be described. , other pigments, a binder resin solution, and a method for producing a green and blue photosensitive coloring composition. &lt;Production method of diketopyrrolopyrrole pigment&gt; (brominated diketopyrrolopyrrole pigment) Formula (1)) In a stainless steel reaction vessel equipped with a reflux tube, 200 parts of a third pentanol dehydrated by molecular sieves and 140 parts of sodium-third-pivalic acid were added under a nitrogen atmosphere, and heated to 10 0 while stirring. After the reaction, the solution was prepared into an alkyd solution. 323842 126 201233734 On the other hand, 88 parts of diisopropyl succinate and 156.6 parts of 4-bromobenzonitrile were added to the glass flask, while stirring The mixture was heated to 9 ° C to dissolve it, and a solution of the mixture was prepared. While the heated solution of the mixture was slowly dropped into the above alkoxide solution heated at 10 ° C for 2 hours, Intense stirring After the completion of the dropwise addition, heating and stirring were continued at 90 ° C for 2 hours to obtain an alkali metal salt of a diketo-based σ-pyrrolidine compound, and 600 parts of decyl alcohol was added to a glass-lined reaction vessel. 600 parts of water and 304 parts of acetic acid, which are cooled to -10 ° C. This is cooled

The mixture was subjected to a high-speed stirring disperser while rotating a shear disk having a diameter of 8 cm at 4000 rpm while adding a small amount of the previously added taudiolone pyrrolopyrrole compound which had been cooled to 75 ° C. Check the metal salt solution. At this time, while the mixture of methanol, acetic acid, and water is cooled, the temperature is maintained at a temperature of -5 ° C or lower, and the addition rate of the metal salt solution of each compound of the compound is adjusted to about 120. A small amount of additions in minutes. After the addition of the metal salt, a color crystal was formed to form a red suspension. Next, the paste was redispersed and cooled to a third to obtain a red paste. The alcohol concentration is about _ after the suspension, at 5. Fortunately, the particles which form the crystal transfer are granulated and washed, and after 3 hours, the obtained diketone group will accompany. 8份。 The src pyrrole pigment 150. 8 parts by squeezing the liquid paste of the formula (1). Shown the bis-ketopyrrolo (specific heterodiketone "Bigidopyrrole 323842 π Λ formula (Α-2-1)) 127 201233734 Adding width = dipentanol 2 2 0 in the reaction vessel 1 For the portion, while cooling the water bath, add 60% NaH 32% by weight.. _. Next, in the reaction vessel 2, the compound of the following formula (A i6) is synthesized by the method of 'the third pentacene 】, φ ^ , X alcohol 100, and Tetrahedron, 58 (2002) 5547 to 5565. Injury 4 cyano linkage 6 〇. 9 parts of heat dissolved, and dropped into the reaction vessel 1 in 2 hours. After im: reaction 1M, time, cooled to 6 ° C, while adding 400 parts of methanol and 50 parts of acetic acid, - edge into

After the hydrazine and methanol cleaning, the formula (A_M) (4) specific heterodioxyl sulphate and 11 pirule pigment A 88. 1 part.

(Specific heterodiketopyrrolopyrrole shot A combined with formula A (A-2-2))

In addition to the 4-cyano-linked stupid 6〇·9 injury was changed to 4-tris-butylbenzonitrile 5.41 parts except for the rest and specific hetero- ΛΙ-mercaptopyrrolopyrrole pigments (A-2 The production of -1) was carried out in the same manner and carried out to 83.9 parts of the specific heterodiketopyrrolopyrrole pigment A represented by the formula (A-2-2). (Specific miscellaneous two shouting scales and t each pigment / - Μ (9) In addition to changing 4-cyanobiphenyl 6 〇 qn ^ hV U · 9 parts to N-butyl-4-cyanobenzoquinone 68 · 7 injuries 'The rest of the disc order...9, the doped diketopyrrolopyrrole pigment Λ ^ The same operation of the 'de() part of the formula U-2-3a) shows the specific heterodithiopyrrolopyrrole Pigment A. 323842 128 201233734 (Specific heterodi- _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ 75. In addition to the injury, the rest is treated with the specific heterodiketone ton p and the ratio of each pigment a (A-2-1). The same operation is carried out to obtain 86. 9 parts of the formula (A-2_3b) The specific heterodiketopyrrolopyrrole pigment A shown. (Specific heterodiketone group pyrrolopyrrole pigment A formula (A_2_4a)) except that 4, 4-cyanobiphenyl 60.9 parts were changed to N, N-dibutyl-4-cyano-p-benzophenone 87.8 In the same manner as in the preparation of the specific heterodiketopyrrolopyrrole pigment A (A-2-1), the specific operation of the formula (A-2-4a) is obtained. Ketopyrrolopyrrole pigment a. (Specific heterodiketopyrrolopyrrole pigment A formula (A_2-4b)) except that 4-cyanobiphenyl 6 〇·9 parts was changed to N,N-dibutyl_3-cyanobenzoquinone 87. The same operation as the production of the specific heterodiketopyrrolopyrrole pigment A (A-2-1) was carried out in the same manner as in the case of 8 parts, to obtain 83 8 parts of the specific hetero group represented by the formula (A-2-4b). Ketopyrrolopyrrole pigment A. (1) (Specific heterodione-pyrrolopyrrole pigment A (A-2-9a)) In addition to the 4-cyanobiphenyl 60.9 parts changed to 4_ (octyl thio) benzoyl nitrile 84. 1 wounded The same procedure as in the production of the specific heterodiketopyrrolopyrrole pigment a (A-2-1) gives 85 5 parts of the specific heterodiketone D shown in the formula (A_2_ga).吼? Each pigment A. (Specific heterodiketopyrrolopyrrole pigment A s (a_2_8)) In addition to the 4 - cyanobiphenyl 60.9 parts changed to 4 _ (three gas f-based) _ benzonitrile 5. 1 injury The specific hetero-residue group b is subjected to the same operation as in the production of the formula of the sirloin pigment, a formula (A-2-1), to obtain 85 8 parts of the specific hetero-fluorenyl group t represented by the formula (A_2_8) 323842 129 201233734 and α 比洛颜... <Two bismuth base material doubling system _ group wire (four) manufacturing method> (specific miscellaneous _ ° _ _ _ mixture (four) - υ) In a non-scale steel reaction vessel with a return pipe, under nitrogen, will pass Molecular sieve dehydration of the third pentanol 2 parts, and the third pentamyl sodium 140 injury added to the side of the mixing while heating in the coffee, prepared into an alkoxide solution. f On the one hand, in a glass flask, 88 parts of diisopropyl succinate, 4 parts of 4_ benzophenone nitrile and 4 parts of 4-cyanobiphenyl ls. i were added, while mixing at 9 Gt It is dissolved to prepare a solution of these mixtures. The heated solution of the mixture was slowly added dropwise to the above-mentioned alkoxide solution heated at a constant rate for 2 hours while stirring vigorously. Drop, ',. After the bundle, the mixture was further heated and heated at 90 C for 2 hours to obtain an alkali metal salt of a bis-pi-pyrrolidine-based compound. Further, sterol 6 was added to a glass-lined reaction vessel. 6 parts of water, 30 parts of water and 304 parts of acetic acid, cooled to -10 ° C. This cooled mixture was spun using a high-speed stirring disperser, and the side of the straight melon was cut at 4 rpm. A metal salt solution of a previously obtained diketopyrrolopyrrole compound cooled to 75 ° C was added thereto in a small amount. At this time, a mixture of methanol, acetic acid, and water was cooled to maintain the temperature. Keeping at _5. (: The following temperature, and adjusting the addition rate of the diketopyrloate and η-Byro compound metal salt solution at 75 ° C) is added in a small amount for about 120 minutes. After adding the alkali metal salt 'The red crystal was precipitated to form a red suspension. Then, the obtained red suspension was washed with an ultrafiltration device at 5 Torr, and then filtered to obtain a red paste. The paste was again dispersed until it was cooled to 3500 323842 130 201233734 0°C In the case where the concentration of methanol is small, the suspension will be transferred with crystallization of ❸49%, and will be removed at 53⁄4, the whole heart/plate is granulated and washed. Then the '3 filter is over/under, and the second will be obtained. The same base q as a substance, at 8 (TC drying for 24 hours, each of the 5 substances of water (9) heterodiketopyrrolopyrrole: two strokes to 143.6 parts of the gas pigment red 254 and the formula.质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量质量%. Open as the content of each pigment A, the specific (different bis-base scale _ pigment mixture in addition to 4-cyano linkage 15 , ()) 13. 4 parts, the rest with the specific miscellaneous = = The manufacture of 4-t-butyl berylate is carried out in the same manner: Obtaining: the mixture of the pyrrole pyrrole pigment mixture is singularly mixed with two _ red 254 and the formula (final 2) _ / this 2). The specific miscellaneous diterpene of the C. sound "Ming UA 2 2" is not the same as the content of the material. When quantitatively analyzed by HPLC, I is more specific than the specific heterodikeke group shown by a. · Yan Yanhong 254 and (A-2 2) 9U quality grade 9.3 mass% of each pigment A content, respectively (specific miscellaneous ton ton slightly 哎 slightly pigment mixture 3 (r two = joint stupid ... part, changed to m chaos醯 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 19 RC_3)e related to • Yan Ke, gong 254 and formula (A-2, the specific heterodithiophene shown 323842 131 201233734 0 than ρ. The content of the specific heterodiketopyrrolopyrrole pigment A, which is represented by the formula (A-2-4a), is 90.8 mass%, respectively. And 9.2% by mass. <Method for Producing Binder Resin Solution> (Preparation of Acrylic Resin Solution 1) A cyclone is placed in a reaction vessel in which a thermometer, a cooling tube, a nitrogen introduction tube, a dropping tube, and a stirring device are attached to a separable 4-neck flask. 196份份为优选为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为为Ester, 12.0 parts of methacrylic acid, 20.7 parts of cumyl phenol oxirane modified acrylate (East Asia Synthetic Co., Ltd. "8 [〇^1\1^110", 1.1 parts of 2 , a mixture of 2'-azobisisobutyronitrile was dropped. After the completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a solution of an acrylic resin. After cooling to room temperature, about 2 parts of the resin solution was used as a sample at 180 °. After heating and drying for 20 minutes, the non-volatile component was measured, and acryloxypropyl acetate was added to the resin solution in which φ was previously synthesized, and the acrylic resin solution 1 was prepared so that the nonvolatile content became 20% by mass. Mass average molecular weight ( Mw) is 26000. (Acrylic resin dissolves Preparation of 2) In a separable 4-necked flask, a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen introduction tube, a dropping tube, and a stirring device was placed, and 207 parts of cyclohexanone was placed, and the temperature was raised to 80 ° C, and the inside of the flask was purged with nitrogen. After the substitution, 20 parts of methacrylic acid and 20 parts of isopropylidene phenol oxirane modified by a dropping tube for 2 hours (ARONIX M110 manufactured by Toagosei Co., Ltd.), 323842 132 201233734 45 parts of a mixture of methyl acetoacetate, 85 parts of methyl propyl ester, and 1 · 33 parts of 2'2'-azobisisobutyronitrile: After dripping, continue the reaction 3 In an hour, the copolymer resin is dissolved; the beam is second, and the total amount of the obtained copolymer solution is -, when the nitrogen gas is stopped, the H is injected, and the dry gas is secreted - after the difficulty, after the cold (four) room temperature, the 6 of the 2 - mercapto propylene oxiranyl ethyl isocyanate (made by Showa Denko)

Karen Logic), 〇. () 8 parts of dibutyltin laurate, _cyclohexanone mixed in m: dripped in 3 hours. About 2 g of the resin solution was used as a sample, and the non-volatile component was measured after 20 minutes of heating, and the cyclohexyl group was added to the previously synthesized resin solution to prepare the acrylic resin by changing the nonvolatile content to 2% by mass. Solution 2. The mass average molecular weight (Mw) is 18,000. <Method for Producing Green and Blue Photosensitive Coloring Composition> (Preparation of Green Photosensitive Colored Composition (GR-1))

After the mixture was stirred and mixed in a uniform manner, a zirconia pellet having a diameter of 0.5 mm was used, and an Eiger mill ("Mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd. was dispersed for 5 hours, and then 5.0. The filtration membrane of β m is passed through, and the green coloring composition 1 (Gp_ 1) is produced. Green pigment (C_I. Pigment Green 36) 6 8 parts of yellow pigment (CI Pigment Yellow 150) 5. 2 parts of resin type dispersant ( "EFKA4300" manufactured by Ciba Japan Co., Ltd.) 1.0 part of acrylic resin solution 1 30.5 parts of propylene glycol monodecyl ether acetate 50.2 parts secondly, the following mixture was stirred and mixed in a uniform manner 323842 133 201233734 1 /zm over; membrane filtration, green photosensitive coloring composition l (GR-l). 42. 0 parts 13. 2 parts of green coloring composition l (GP-l) acrylic resin solution 2 photopolymerization Separate single-body ("ARONIX M400" manufactured by Toagosei Co., Ltd.) 2. 8 parts of photopolymerization initiator ("Iggure_9〇7" manufactured by Ciba Japan Co., Ltd.) 2. Oxide sensitizer ("ααβ-" manufactured by Hodogaya Chemical Co., Ltd.份份份份份份份份份份份份份份份份份份份份份份份份份份份份份份份

(Preparation of blue photosensitive coloring composition l (BR-1)) After mixing and mixing the following mixture in a uniform manner, a zirconium dioxide sphere having a diameter of 0.5 mm was used, and an Eiger mill (Eiger) was used. The "Mini model M-250 MKII" manufactured by Nippon Co., Ltd. was dispersed for 5 hours, and then filtered through a filtration membrane of 5. 〇A m to prepare a blue colored composition 1 (bp-1). Blue pigment (CI Pigment Blue 15: 6) 7. 2 parts of purple pigment (CI Pigment Violet 23) 4. 8 parts of resin type dispersant ("ACKA4300" manufactured by Ciba Japan) 1. Resin acrylic resin solution 1 30.5 parts of propylene glycol monomethyl ether acetate 52. 0 parts, the mixture of the following composition was stirred and mixed in a uniform manner, and then filtered through a filtration membrane of 1/m to prepare a blue photosensitive coloring composition 1 (BR-1). 1 (BP-1) 34. 0 parts of acrylic resin solution 2 15. 2 parts of photopolymerizable monomer ("ARONIX M400" manufactured by Toagosei Co., Ltd.) 3·3 parts 323842 134 201233734 Photopolymerization initiator (steam) "Irgacure-907" made by Ba Japan Co., Ltd. 2. 0 parts of sensitizer (EAB-F1, manufactured by Hodogaya Chemical Co., Ltd.) 0. 4 parts 1份 [Formula 1] (Production of the pigment composition l (Rl)) The brominated diketopyrrolopyrrole pigment of the formula (1): 99 parts, formula (A- 2-1) A specific heterodiketopyrrolopyrrole pigment A 1.0 part, 1000 parts of sodium vapor, and 120 parts of diethylene glycol, placed in a stainless steel 1 gallon kneader® (manufactured by Inoue Co., Ltd.) The mixture was kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, and heated at about 80 ° C, and then scrambled for 1 hour to form a paste, which was filtered and washed with water to remove salt and diethylene glycol. After drying at 80 ° C for one day and night, by pulverization, 96.9 parts of the diketopyrrolopyrrole pigment composition 1 (R-1) was obtained, and the average primary particle diameter was 37. Onm. [Example 2] ( Manufacture of the pigment composition 2 (R-2) φ In addition to the brominated diketopyrrolopyrrole pigment of the formula (1): 99 parts, the specific heterodiketopyrrolopyrene of the formula (A-2-1) Pyrrole pigment A 1. 0 parts, changed to the brominated diketopyrrolopyrrole pigment of formula (1) 97. 0 parts, the specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1) 3.0 parts Other than the pigment composition l ( 5质量。 [Embodiment 3] (Pigment composition 3 ((Pigment composition 3) (Immediate primary particle diameter is 36. 8 nm. [Example 3] (Pigment composition 3 ( Manufacture of R-3) 323842 135 201233734 In addition to the brominated diketopyrrolopyrrole pigment of formula (1), 99. 0 parts, specific heterodiketopyrrolopyrrole pigment A of formula (Α-2-1) 1. 0 parts, changed to the brominated diketopyrrolopyrrole pigment of the formula (1), 9. 5 parts, of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2 -1), 5.0 parts 2份。 The same as the production of the pigment composition l (Rl) in the same manner to obtain a diketopyrrolopyrrole pigment composition 3 (R-3) 97.2 parts. The average primary particle diameter is 30.5 nm. [Example 4] • (Production of Pigment Composition 4 (R-4)) The specifics of the brominated diketopyrrolopyrrole pigment of the formula (1): 99 parts, formula (A-2-1) a part of the heterodione-pyrrolopyrrole pigment of the formula (1), and a specific heterodiketopyrrole of the formula (A-2-1). 9份。 The same as the production of the pigment composition l (Rl), the same procedure to obtain a diketopyrrolopyrrole pigment composition 4 (R-4) 96.9 parts. The average primary particle diameter is 28.5 nm ° [Example 5] (Production of Pigment Composition 5 (R-5)) In addition to the brominated diketopyrrolopyrrole pigment of the formula (1): 99 parts, formula ( A-2-1) a specific heterodiketopyrrolopyrrole pigment A 1. 0 parts, changed to a brominated diketopyrrolopyrrole pigment of formula (1) 85. 0 parts, formula (A-2-1 The same procedure as in the preparation of the pigment composition l (Rl) to obtain a diketopyrrolopyrrole pigment composition 5 (R-5) except for the specific heterodipypyrrolopyrrole pigment A of 15.1 parts ) 97. 3 copies. The average primary particle diameter is 323842 136 201233734 29. 5nm. [Example 6] (Production of Pigment Composition 6 (R-6)) The specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the formula (A-2-2). The same procedure as in the preparation of the pigment composition 3 (R-3) except for the specific heterodiketopyrrolopyrrole pigment A, to obtain a diketopyrrolopyrrole pigment composition 6 (R-6) 98. 1 serving. The average primary particle diameter is 29.9 nm. [Example 7] (Production of Pigment Composition 7 (R-7)) In addition to the specific heterodiketobenzopyrrole pigment A of the formula (A-2-1), it is changed to the formula (A-2- In the same manner as in the production of the pigment composition 3 (R-3) except for the specific heterodikedo-pyrrolopyrrole pigment A of 3a), a diketopyrrolopyrrole-based pigment composition 7 (R- 7) 98. 0 copies. 7纳米。 The average primary particle diameter is 30.7 nm. φ [Example 8] (Production of Pigment Composition 8 (R-8)) The specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the formula (A-2-3b). In the same manner as in the production of the pigment composition 3 (R-3) except for the specific heterodiketopyrrolopyrrole pigment A, a diketopyrrolopyrrole pigment composition 8 (R - 8) 9 was obtained. 8. 4 copies. 2纳米。 The average primary particle diameter is 31.2 nm. [Example 9] (Production of Pigment Composition 9 (R-9)) 323842 137 201233734 In addition to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1), the formula (A-2) was changed. In the same manner as in the production of the pigment composition 3 (R-3) except for the specific heterodiketopyrrolopyrrole pigment A of -4a), a diketopyrrolopyrrole pigment composition 9 (R) was obtained. -9) 97. 5 servings. The average primary particle diameter is 35.4 nm. [Example 10] (Production of Pigment Composition 10 (R-10)) The specific heterodiketopyrrolopyrrole pigment A, ® of the formula (A-2-1) was changed to the formula (A-2-4b). The specific heterodithiol β ratio is different from p and π is the same as the pigment A of each of P, and the same operation as in the production of the pigment composition 3 (R-3) is carried out to obtain a diketopyrrolopyrrole pigment composition. 10 (R-10) 96. 6 parts. The average primary particle diameter is 35.8 nm. [Example 11] (Production of Pigment Composition ll (R-ll)) In addition to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1), φ was changed to the formula (A-2-9a) The same operation as in the production of the pigment composition 3 (R-3) except for the specific heterodiketopyrrolopyrrole pigment A, to obtain a diketopyrrolopyrrole pigment composition 11 (R-ll) 93. 9 copies. 4纳米。 The average primary particle diameter is 32. 4nm. [Example 12] (Production of Pigment Composition 12 (R-12)) The specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the formula (A-2-8). The same operation as the preparation of the pigment composition 3 (R-3) except for the specific heterodiketopyrrolopyrrole pigment A was obtained, and 323842 138 201233734 to diketopyrrolopyrrole pigment composition 12 (R) was obtained. -12) 95. 7 copies. 8纳米。 The average primary particle diameter is 29. 8nm. [Example 13] (Production of Pigment Composition 13 (R-13)) Brominated diketopyrrolopyrrole pigment of the formula (1) 98. A commercially available ci Pigment Red 254 (Ciba Specialty Chemicals Co., Ltd.) "Irgaph〇r Red B-CF" 1. A 1.0 part of a specific heterodiketopyrrolopyrrole pigment A of the formula (Α_2-ι), 1 part of sodium gasification, and 12 parts of diethylene glycol The mixture was placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 6 (rc for 1 hour). The mixture was poured into warm water while stirring, and stirred for about 1 hour while heating. After the paste, filtered and washed with water to remove salt and diethylene glycol, 'dry at 80 ° C for one day and night, by pulverization to obtain 96.7 parts of diketopyrrolopyrrole pigment composition 13 (R-13), The average primary particle diameter is 33. 2 nm. [Example 14] (Production of Pigment Composition 14 (R-1)) In addition to the brominated diketone σ ratio of the formula (1), the ratio of the pigment gg. 〇 And commercially available C·I·Pigment Red 254 (Irgaphor RedB-CF) made by Ciba Specialty Chemicals Co., Ltd. 1.0 part, and specific heterodiketopyrrolopypene pigment A 1 of formula (a_2-i) 0 injured, The evolution of the formula (1) is 20.0 parts per ton of lop-pyro-pyrazine pigment, and the commercially available CI pigment red 254 ("Irgaphor RedB-CF" manufactured by Ciba Specialty Chemicals Co., Ltd.). The same operation as the preparation of the pigment composition 13 (R-13) was carried out in the same manner as in the preparation of the specific heterodiketopyrrolopyrrole pigment A of -2 - D to obtain 98.3 parts of diketopyrrole 323842 139 201233734 And the pyrrole-based pigment composition 14 (R-14), the average primary particle diameter is 30. 2 nm 〇 [Example 15] (Production of Pigment Composition 15 (R-15)) In addition to the bromination of the formula (1) Ketopyrrolopyrrole pigment 98.0 parts, commercially available CI Pigment Red 254 (Irgaphor Red B-CF) made by Ciba Specialty Chemicals Co., Ltd. 1.0 part, and specific heterodiketone of formula (A-2-1) The pyridylpyrrole pigment A 1. 0 parts, changed to the brominated diketopyrrolopyrrole® material of the formula (1) 50. 0 parts, commercially available CI Pigment Red 254 (Irgaphor, Ciba Specialty Chemicals Co., Ltd. 45 parts of Red B-CF", and 5.0 parts of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1), the same as the production of the pigment composition 13 (R-13) operating, 97 parts of a diketopyrrolopyrrole pigment composition 15 (R-15) was obtained, and the average primary particle diameter was 26.7 nm. [Example 16] • (Production of Pigment Composition 16 (R-16)) In addition to 98.0 parts of the brominated diketopyrrolopyrrole pigment of the formula (1), commercially available CI Pigment Red 254 (Irgaphor Red B-CF, 1.0 part by Ciba Specialty Chemicals Co., Ltd., and Formula (A-2-) 1), a specific heterodione-pyrrolopyrrole pigment A 1. 0 parts, changed to a brominated diketopyrrolopyrrole pigment of the formula (1) 20.0 parts, a commercially available CI pigment red 254 (Ciba special 72.0 parts of "Irgaphor Red B-CF" manufactured by Chemical Co., Ltd., and 8.0 parts of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1), and the pigment composition 13 (R-13) The same procedure was carried out to obtain 94.8 parts of diketopyrrole 323842 140 201233734 and a pyrrole pigment composition 16 (R-16) having an average primary particle diameter of 28. Onm. [Example 17] (Production of Pigment Composition 17 (R-17)) In addition to the brominated diketopyrrolopyrrole pigment of the formula (1), 90.0 parts, commercially available CI Pigment Red 254 (Ciba Special) 1.0 part of "Irgaphor Red B-CF" manufactured by Chemical Co., Ltd., and the specific heterodiketone ratio of the formula (A-2-1), and the ratio of the B-pyrrome pigment A to the formula (1). 2 parts of brominated diketopyrrolopyrrole® material, commercially available CI Pigment Red 254 (Irgaphor Red B-CF, manufactured by Ciba Specialty Chemicals Co., Ltd.) 65.0 parts, and formula (A-2- 1) The diketone pyrrolopyrrole pigment is obtained in the same manner as in the preparation of the pigment composition 13 (R-13). The composition 17 (R-17), the average primary particle diameter was 29.3 nm. [Example 18] φ (Production of Pigment Composition 18 (R-18)) The brominated diketopyrrole of the formula (1) 0. 0 parts, a specific heterodiketopyrrolopyrrole pigment mixture 1 (RC-1) 20.0 parts, sodium chloride 1000 parts, and diethylene glycol 120 parts, put into a stainless steel 1 gallon kneading Machine (manufactured by Inoue Manufacturing Co., Ltd.), mixing at 60 ° C 10 Next, the kneaded mixture was poured into warm water, stirred while heating at about 80 ° C for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at 80 ° C for a day and night. 9份。 By pulverization, 96.9 parts of the diketopyrrolopyrrole pigment composition 18 (R-18) was obtained, and the average primary particle diameter was 29.2 nm. 323842 141 201233734 [Example 19] (Pigment composition 19 (R) -i9) Manufacture) In addition to the specific heterodiketone-based haha and the specific heterodiketopyrrolopyrrole pigment mixed with three substances (叱, 1), the rest with the pigment composition 180M8) 5微米。 ^ ^ ^ ^ 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2

[Example 20] ' (Production of Pigment Composition 20 (R-20)) l) In addition to changing the specific heterodiketopyrrolopyrene 11 to a specific heterodiketone η ratio P and U Biha pigment Now eight objects ~ material 1 (Rc, outer 'the rest and pigment composition 18 (R~18) are made into / (叱*~3) to get 9 5 · 4 parts of diketopyrrolopyrrole pigment 缒仃The same operation 20 (R-20), the average primary particle diameter is 31·inm. The product [Example 21] (Production of Pigment Composition 21 (R-21)) Formula, Formula (7ί) ^ 12〇 (1) The specific heterodiketopyrrolopyrrole pigment of the brominated diketopyrrolopyrrole pigment 95 (A-2-1). The pigment derivative of the quinone portion 5. 0 parts, sodium chloride 1 〇〇〇 And, for your part, put into a stainless steel 1 gallon kneader (mixed in the broth C for 1 hour in the well. Secondly, put the mixture into the warm water: stir while heating at about 80 ° C After 1 hour, it was made into a paste, filtered and washed with water to remove salt and diethyl alcohol, and then dried at 8 Torr. After drying for one night, 91.8 parts of diketopyrrolopyrrole pigment composition 323842 142 201233734 21 (R-21) The average-secondary particle diameter is 27·4 (10). [Example 22] (Production of Pigment Composition 22 (R-22)) The desertified diketone group of the formula (1) and each of the scale pigments 8 parts of a commercially available CL Pigment Red 254 (manufactured by Ciba Specialty Chemicals Co., Ltd. (6) μ B-CF" 18.G, specific heterodiketone squash pigment A of formula (A-2-1) 2.0 parts, formula (7-1) The pigment derivative 5 〇 part, gasified 诵 诵 part, and diethylene glycol 120 parts, in the human τ β β ~, won the stainless steel 1 gallon kneader (Inoue • Manufacturing), at 6 〇t Mixing for 1 hour. Secondly, the mixture is mixed into warm water, and then dried at about 8 (heated in rc (four) for 1 hour to make a paste' rhyme and washed with water to remove salt and diethylene glycol, then dry - By day and night, 91.3 parts of the diketone base material was obtained by pulverization and the pigment composition 22 (R-22) was obtained, and the average primary particle diameter was 29. [Reference Example 1] * (Pigment composition 23 (R- 23) Manufactured by the change of the odorized diketone group of the formula (1) to the commercially available CI Pigment Red 254 ("Chuba Special Chemicals Co., Ltd." Other than -CF", the rest with pigment Production of Composition 4 (R_4) The same operation was carried out to obtain 96.0 parts of a diketone-based squash pigment composition 23 (R-23) 'The average primary particle diameter was 3 〇 9 nme [Reference Example 2] (Pigment composition) The manufacture of the product 24 (R-24)) The desertified bis-base scale of the formula (1) and 1000 parts of the gasification of each pigment, and 120 parts of the diethylene glycol, the rose into the Kneading 323842 143 201233734 machine (manufactured by Inoue Seisakusho Co., Ltd.), kneading at 60 ° C for 10 hours. Next, the kneaded mixture is poured into warm water, and stirred for about 1 hour while heating at about 80 ° C to form a paste. After drying and removing the salt and diethylene glycol, the mixture is dried at 80 ° C.纳米。 The average particle diameter is 33. lnm. The granules are obtained by pulverization. [Reference Example 3] (Production of Pigment Composition 25 (R-25)): In addition to the brominated diketopyrrolopyrrole pigment of the formula (1), 95. 0 parts, and the formula (A-2-1) The specific heterodione-pyrrolopyrrole pigment A 5. 0 parts, changed to the brominated diketopyrrolopyrrole pigment of the formula (1) 70. 0 parts, and the specific heterodione of the formula (A-2-1) The same operation as the preparation of the pigment composition l (R1) was carried out in the same manner as in the production of the pigment composition 1 (R1) to obtain 98.0 parts of diketone D to 17 and 11 to p of each pigment composition 25 6nm。 The average primary particle diameter is 28. 6nm. φ [Reference Example 4] (Production of Pigment Composition 26 (R-26)) In addition to the brominated diketopyrrolopyrrole pigment of the formula (1), 90.0 parts, commercially available CI Pigment Red 254 (Ciba "Irgaphor Red B-CF" manufactured by Special Chemicals Co., Ltd. 1.0 part, a specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1), 1.0 part, changed to the brominated two of formula (1) a ketopyrrolopyrrole pigment of 1 part, a commercially available CI Pigment Red 254 ("Irgaphor Red B-CF" manufactured by Ciba Specialty Chemicals Co., Ltd. 65.0 parts, a specific heterodiketone of the formula (A-2-1) The same operation as in the manufacture of the pigment composition 323842 144 201233734 13 (R-13) was carried out to obtain 95. 1 part of a diketopyrrolopyrrole pigment composition 26 (except for 20.0 parts of the pyridylpyrrole pigment A). R-26), the average primary particle diameter is 29.5 nm [Reference Example 5] (Production of Pigment Composition 27 (R-27)) In addition to the brominated diketopyrrolopyrrole pigment of the formula (1), Manufactured in the same manner as in the manufacture of the chemically-produced CI Pigment Red 254 ("Irgaphor RedB-CF" manufactured by Ciba Specialty Chemicals Co., Ltd., and the other pigment composition 24CR-24) to obtain 98.1 parts of the diketone group. D The ratio of the average primary particle diameter is 34. 9 nm. [Reference Example 6] (Manufacture of Pigment Composition 28 (R-28)) and Japan Special Table 2011 The compound of Example 1016 of -523433 was synthesized in the same manner to obtain a pigment composition 28 (R-28) of the diketopyrrolopyrrole pigment of the formula (1) and the following formula (A-17).

Formula (A-17) [Reference Example 7] (Production of Pigment Composition 29 (R-29)) The same method as Example 1039 of JP-A-2011-523433 323842 145 201233734 Synthesis of the second material of the formula (1) The pigment composition 29 (R-29) formed by the pigment and the following formula (A-18).

The contents of the pigment compositions 1 to 29 (R-1 to 29) to be produced are shown in Table A-1. "PR254" shown in Table 1 means C.I. Pigment Red 254. [Table A-1] &amp;A- 1

Pigment composition two W-pyridolipid pyrrole pigment AP Y Y 〒 4 color derivative conversion material 1 mass X pigment 2 mass X child 3 quality 璧 X Example 1 R-1 Formula (1) 99 Λ ΪΑ-2 - 1) 1 - - - - Example 2 R-2 Formula (1) 9 7 Formula (A-2-n 3 - - - - Example 3 R-3 Formula (1) 9 5 Formula (Α-2- 1 1 5 - — - — 1Γ艳洌4 R-4 Formula (1) 9 0 Formula (Α-2- 11 10 一一 - Example 5 R-5 Formula (1) 8S Formula (A-2-li 1 5 I—*· — Example 6 R-6 Formula (1) 95 Κ (Α-2-2) 5 - _ - ' Poor W 7 R-7 Formula (1) 95 Formula (Α-2-3ίΐ) S One-one - Implement W8 R -8 Formula (1) 95 Formula (A-2-3hl 5 - I - ' Implement W9 R-9 Formula (1) 9S Formula (A- 2 - 4 a) 5 - - • * &lt;Example 1 0 R- 1 0 (1) 95 Formula (A- 2 -4 b) 5 - A - Solid example 1 1 R-1 1 Formula (1) 95 Formula (A, 2-9al 5 - I - Barren W1 2 R- 1 2 Formula (1) 9 5 Formula CA-2-81 S - • - - Example 1 3 R- 1 3 Formula (1) 9 8 Formula (A-2 - η 1 PR 2 54 1 9 9:1 - Example 1 4 R-1 4 Formula (1) ao Λ (Λ-2 - 1) 2 PR 2S4 18 8 2:18 - Poor Example 1 5 R- 1 5 Formula (1) 5 0 Formula (A* 2 - η 5 PR 2 54 4 5 5 3:47 - Example 1 6 R-1 6 Formula (1) 2 0 Formula (α-2-η 8 PR 2 5 4 7 2 2 2:78 Real 旄W1 7 R-1 7 Formula (1) 2 0 Formula (A-2-η 15 PR 2 54 6 5 24:76 - Example 1 8 R- 1 8 Formula (1) 8 0 Formula (A-2- 1&gt; 2 PR 2 54 18 &quot; 82:18 Example 1 9 R-1 9 Formula (1) 80 Formula (A - 2-2 &gt; 2 PR 2 54 1 8 82:18 Scenario 2 0 R 20 Formula (1) 8 0 Formula (A-2 - 4 al 2 PR 2 54 18 8 2:18 - Example 2 1 R-2 1 Formula (1) 9 5 Formula &lt;A-2-l&gt; 5 - - ^ (? - η Poor Example 2 2 R-22 Formula (1) 80 Formula &lt;A-2-l&gt; 2 PR 254 18 8 2 : 1 R 5 (7-η Reference Example 1 R-23 - - Formula &lt;Α·2-1&gt; 10 PR 254 9 0 Example 2 R-24 Type (1, 1 0 0 • One • - - - Reference Example 3 R-2 5 Formula (1) 7 0 Formula &lt;Α-2-1&gt; 3 0 - - — Take the test W4 R-26 Formula (1) 15 ^ (A-2-n 2 0 PR 2 5 4 6 5 19:81 —_ Reference Example 5 R-27 - - - PR 254 1 0 0 - Reference Example 6 R- 2 8 Equation (1) 8 2 Equation 1 (A-1 7&gt; 18 ~ Reference Example 7 R-29 (1) 11 - - Formula (A-1 8) 8 9 [Example 23] 146 323842 201233734 (Production of coloring composition 1 (R 丨)) ^ Mix the mixture of it into a uniform and use straight The coloring composition 1 (Rp i) was prepared by filtering through a ruthenium membrane of an Eiger grinder ("i model M-250 MKII" manufactured by Eiger Japan Co., Ltd. for 5 hours and then 5, 〇"). . Diketopyrrolopyrrole pigment composition 1 (R-1) 11. 0 parts of pigment derivative formula (14-1) 1.0 part acrylic resin solution 1 40. 0 parts propylene glycol monomethyl ether acetate 48. 0 parts [ Examples 24 to 44] (Production of Colored Compositions 2 to 22 (RP-2 to 22)) In addition to changing the pigment composition 1 (R1) to the pigment composition described in Table A-2, Composition 1 (RP-1) was subjected to the same operation to prepare colored compositions 2 to 22 (RP-2 to 22). [Example 45] % (Production of the coloring composition 23 (RP-23)) The following mixture was stirred and mixed, and it was attempted to make it uniform, and a diameter of 0.5 mm of a dioxide ball was used, and an Eiger mill (Eiger) was used. The "Mini model M-250 MKII" manufactured by Nippon Co., Ltd. was dispersed for 5 hours, and then filtered through a filtration membrane of 5.0&quot; m to prepare a colored composition 23CRP-23). Di-p-pyrrolopyrrole pigment composition 2 (R-2) 11.0 parts of pigment derivative Formula (6-3) 1.0 part of resin-type dispersant 6.0 parts ("BYK161" manufactured by Byk Chemie Co., Ltd. (30 ° / solution) 323842 147 201233734 31.0 parts 51.0 parts of acrylic resin solution 1 propylene glycol monomethyl ether acetate [Example 46] (Production of coloring composition 24 (RP-24)) The following compound was mixed and mixed to form a uniform , using a diameter of 〇. 5min of cerium oxide pellets, Eiger grinding machine ("Eiger Japan" "Mini

After the model M-250 MKII was dispersed for 5 hours, it was filtered through a filtration membrane of 50%, and a colored composition 24 (RP-24) was produced. Diketopyrrolopyrrole pigment composition 2 (R_2) 12.0 part resin type dispersant ("Ajisper ΡΒ82ΐ" manufactured by FINETECHNO Co., Ltd.) 23·0 parts 61. 4 parts acrylic resin solution 1 propylene glycol monoterpene acetic acid Ester [Reference Examples 8 to 14] (Production of Colored Compositions 25 to 31 (RP-25 to 31)) In addition to changing the pigment composition 1 (ΙΜ) to the pigment composition described in Table A-2, The composition ΚΚΡΜ) was subjected to the same operation to prepare colored compositions 25 to 31 (RP-25 to 31). <Evaluation of Coloring Composition> (Production of Contrast Measurement Substrate) The coloring compositions obtained in Examples 23 to 46 and Reference Examples 8 to 14 were 4 on a glass substrate having a thickness of 1 mm x 10 mm, 〇 7. The film thickness was applied to x = 〇.64 () in c light and dried. Into the step, to the coffee ^ heat for 60 minutes to get a red film. 323842 148 201233734 (Contrast Ratio Evaluation of Coating Film) Description of the measurement method for the contrast ratio of the coating film. The light emitted from the backlight unit for a liquid crystal device is polarized by a polarizing plate, and a dried coating film of a colored composition is applied onto a glass substrate to reach a polarizing plate. As long as the polarizing surfaces of the polarizing plate and the polarizing plate are parallel, although the light passes through the polarizing plate, when the polarizing surface is straight, the light is blocked by the polarizing plate. However, when the polarizing plate passes through the dried coating film of the coloring composition by the polarizing plate, scattering due to the pigment particles, etc., when one of the polarizing surfaces is staggered, the polarizing plate penetrates the polarizing plate when they are parallel. The amount of light is reduced, and a part of the light penetrates the polarizing plate when the polarizing plate is straight. This transmitted light is taken as the ratio of the brightness at the time when the nose-out polarizing plate is parallel and the brightness at the time of straight-line (contrast ratio). (Brightness when contrast is parallel to )) / (Brightness when going straight) Therefore, when the pigment in the coating film is scattered, the brightness in parallel is lowered, and since the brightness during straight running is increased, the contrast ratio becomes %. . At the same time, as a degree-free meter, a polarizing plate ("NPF-G1220DUN" manufactured by Nitto Denko Corporation) was used as a polarizing plate. At the same time, in order to block the excess light during the measurement, a black mask having a square hole of 1 cm was placed on the measurement portion. <Viscosity stability evaluation> (Measurement of initial viscosity and time-increasing viscosity) The viscosity of the coloring composition is an E-type viscometer ("eld viscosity meter" manufactured by Toki Sangyo Co., Ltd.) on the day when the coloring composition is prepared. At 2 5 . Speculation 323842 149 201233734 Initial viscosity. So, about 40. (: After 7 days from the date of setting the self-modulating coloring composition, after the temperature of the sample is returned to 25 ° C, the viscosity is measured according to the above viscosity measurement method, and the time-increasing viscosity is obtained by the following formula. Time-dependent viscosity increase = (time-dependent viscosity) / (initial viscosity) χ丨〇〇 (0 / 〇) (Evaluation of initial viscosity, time-dependent viscosity increase) About viscosity stability, by time The viscosity increase rate is used for evaluation. σ If the time-increasing rate is not paid above, there is practical resistance to ' _ I·sheng beyond this range, there will be a decrease in viscosity or increase in viscosity, and the coloring composition will be coated. When it is coated on a glass substrate, it cannot be coated under the same coating conditions, and there is a problem in productivity. More preferably, it is less than 110% in the range of _. 〇. The viscosity increase rate over time is 90% or more. Up to 11〇% △, Star β Temple viscosity increase rate of 80% or more did not reach 9〇%, or m乂 did not reach 1 win X. The time-increasing viscosity rate did not reach 80%, or 12〇% or more 323842 150 201233734 [ Table A-2] Table A-2 Practical Example 2 3 Example 2 4 Coloring Newborns Pigment Pigment Pigment Derived Eucalyptus Temple Funding Assessment Evaluation Junction Contrast Ratio 3 9 00 Viscosity Stability 0 RP-1 RP-2 R- 1 R- 2 Formula (1 4 - 1 , Practical Example 2 5 Implementation Tree 2 6 RP-3 RP-4 R-3 R _ 4 A v 1 4 — 1 ) 1 4 - 1 , Formula (1 4 - 1 &gt; - 4 0 0 0 4 15 0 ο ο ο Example 2 7 RP- 5 R-5 ^ (1 4-n 4 6 5 0 〇 2 8 RP-6 R-6 Formula U 4- n — 4 0 5 0 〇R P- 7 R-7 Formula (l 4-n _ 4 10 0 0 η Example 3 0 R P- 8 R-8 Formula (1 4 - 1 i 4 10 0 〇Τ Green Example 3 1 Example 3 2 R P- 9 RP-X 0 R-9 R - 1 0 Formula (i 4- n - 4 100 〇 Example 3 3 RP-1 i Rl 1 A 11 4 — 1 i Formula (1 4 — 1 1 1 40 0 0 5 2 0 0 ο 赏 赏 3 3 RP-1 2 R- 1 2 式 &lt;1 4: ΰ 1 _ 3 7 0 0 〇 Example 3 〇 秣 3 3 6 RP-1 3 RP- 1 4 R- 1 3 ^ (14-13⁄4 40 0 0 0 Example 3 7 Poor Example 3 8 RP-1 5 RP-1 6 R- 】S R- 1 6 watts (1 4 -&quot; (14 - η (1 4 - 1 &gt; - 3 8 5 0 4 10 0 4 3 0 〇〇ο M «C> iH *9 旄Tree 4 0 RP- 1 7 RP-1 8 Rl 7 R- l 8 ^ (1 4 - η Formula (1 4- η - 4 3 0 0 3 8 5 0 ο 实 实 例 4 1 Example 4 2 RP - 1 9 RP-2 0 Rl 9 R- 2 0 Formula &lt;im - 3 7 5 0 〇实妹例4 3 RP-2 1 R-2 1 Λ V 1 4 — 1 &gt; Formula &lt;ι 4-n 3 7 0 0 4 2 0 0 〇〇RP-2 2 R-2 2 Formula (1 4-η ......... ο η η 〇 花 W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W RP-2 5 R-2 R-23 Ajisper PB fi 2 1 3400 3 3 0 0 〇〇Reference example 9 RP-26 R-24 2C (1 4-1) 3 η η 0 X Reference example 1 0 RP- Z 7 R-2 5 Formula &lt;1 4- η S 9 S 0 X Reference example 1 JI RP-2 8 R-2 6 Formula (1 4-1) __ 3 3 0 0 Δ Reference cut 1 2 Reference example 1 3 RP-2 9 R-27 Formula (1 4-1) — 2 15 0 X Reference Example 1 4 RP-3 1 R — 2 8 _ R-2 9 2: (1 4-1) _Form and 1 4- η = 2 5 3 0 C --- 2 3 0 0 Δ • &lt;Production method of other coloring composition&gt; (Production of coloring composition 32 (RP-32)) After mixing and mixing the following mixture into a uniform After dispersing for 5 hours using an Eiger grinder ("Mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using a 〇5mnl diameter 〇5mnl filter, it was filtered through a 5.00/zm filter membrane to prepare a colored composition 32 ( RP-32). Diterpenoid pigment (PR177-1) 10. 8 parts of pigment derivative formula (8-5) 1.2 parts of acrylic resin solution 1 40. 151 151 323842 201233734 propylene glycol monoterpene ether acetate 48. 0 parts [Example 47 (Preparation of photosensitive coloring composition l (RR-1)) The following mixture was stirred and mixed to be uniform, and then filtered using a filtration membrane of 1 // m to prepare a photosensitive coloring composition KRhi). Coloring composition l (RP-1) 38. 4 parts of coloring composition 32 (RP-32) 3·6 parts of acrylic resin solution 2 13. 2 parts of photopolymerizable monomer (rAR〇NIX M4〇〇 manufactured by Toagosei Co., Ltd.) 2. 8 parts of photopolymerization initiator (rIrgacure_9〇7, manufactured by Ciba Barbine Co., Ltd.) 2.0 parts of sensitizer (EAB-F, manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts of ethylene glycol monomethyl ether acetate 39. 6 parts [Examples 48 to 72] (Production of photosensitive coloring compositions 2 to 24 (RR-2 to 24)) In addition to changing the coloring composition KRP-i) to the coloring composition 2 to φ 24 (RP-2 to 24) ' At the same time, except that the ratio of the coloring compositions 2 to 24 (RP-2 to 24) to the coloring composition 32 (RP-32) was adjusted in such a manner that Example 47 became the same chromaticity, the rest was carried out in the same manner as in Example 47. Photosensitive coloring compositions 2 to 24 (rr-2 to 24) were produced in the same manner. [Reference Examples 15 to 21] (Production of photosensitive coloring compositions 25 to 31 (RR-25 to 31)) In addition to coloring composition The substance KRP-U was changed to the coloring composition 25 to 31 (RP 25 to 31)'. Further, the coloring compositions 25 to 31 (RP-25 to 31) and the coloring composition were adjusted in such a manner that Example 47 became the same chromaticity. &quot The photosensitive coloring compositions 25 to 31 (RR-25 to 31) were produced in the same manner as in Example 47 except that the ratio of the material 32 323842 152 201233734 CRP-32) was carried out. <Evaluation of Photosensitive Coloring Composition> (Color characteristics, contrast ratio (CR) evaluation) The photosensitive coloring compositions obtained in Examples 47 to 72 and Reference Examples 15 to 21 were placed on a glass substrate having a thickness of 100 mm X 100 mm and 0.7 mm in a C light source. When the film thickness is χ=〇. 640, y=0·328, the photosensitive coloring composition is applied and dried, and the ultraviolet ray of 300 mJ/cm 2 is irradiated with an ultrahigh pressure mercury lamp. Further, it is heated at 230 ° C. A red coating film was obtained in 60 minutes. Then, the brightness (γ) and contrast ratio (c R ) of the obtained coating film were measured. Meanwhile, 'chromaticity and brightness (Y) are microscopic spectrophotometers (manufactured by 〇lympus Optics Co., Ltd.) Measurement of OSP-SP200") (Evaluation of crystal precipitation on the surface of the coating film) The photosensitive coloring compositions obtained in Examples 47 to 72 and Reference Examples 15 to 21 were placed on a glass substrate having a thickness of 100 mm X 100 and a thickness of 0.7 mm. , φ is applied to the c light source so that the film thickness becomes χ=〇·640 After the photosensitive coloring composition 'and dried, irradiated with ultraviolet rays using an ultrahigh pressure mercury lamp 300mJ / cm2 of. Subsequently, after heat treatment for 23 minutes at TC (TC), heat treatment was repeated twice at 240 ° C for 60 minutes. The surface of the substrate coating film after the heat treatment was observed by an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria. : After heat treatment at 230 ° C for 6 minutes, further 24 (TC heat treatment for 60 minutes, and then 24 (TC heat treatment for 60 minutes, no crystal precipitation 〇: 230 ° C heat treatment for 6 〇 minutes, and then 24 (rCM heat treatment 323842 153 201233734 no crystal precipitation for 60 minutes (the second time 24 (the rc heat treatment rib minute crystal precipitation) △: no crystal precipitation after heat treatment at 230 ° C for 60 minutes, but further 240 ° C heat treatment for 60 minutes, crystal precipitation X: crystallization at 230 ° C for 60 minutes, crystal precipitation [Table A-3]

From the results of Table A-3, in the formation of a color filter, in a bis-base squama pigment composition containing a brominated diketopyrrolopyrrole pigment and a specific heterodiketopyrrolopyrrole pigment A The content of the specific heterodithiopyrrolopyrrole pigment A is 1% by mass to 15% by mass of the diketone based on the total mass of the diketopyrrolopyrrole pigment 323842 154 201233734. In the examples of the bismuth pigment composition, particularly in terms of brightness, there is a high contrast ratio, and crystallization of the diketopipharbene pigment by the heating step can be suppressed. <Production of Color Filter> A green photosensitive coloring composition and a blue photosensitive coloring composition used in the production of a color filter were produced. Meanwhile, regarding the red color, the photosensitive coloring composition 2 (RR-2) of the present Example A was used. ® a black matrix processing pattern on a glass substrate, and the photosensitive coloring composition 2 (RR-2) was applied by spin coating on the substrate to a film thickness of x = 〇 640 ' y = 0.328 A colored film is formed. The film was irradiated with ultraviolet rays of 300 mJ/cm2 using an ultrahigh pressure mercury lamp through a mask. Next, after the unexposed portion was removed by spray development using an alkali developing solution of a 0.2% by mass aqueous solution of sodium carbonate, the substrate was washed with ion-exchanged water, and the substrate was heated at 23 (rc for 20 minutes, A red filter segment is formed. By the same method, #鲁绿色色性性组成物KGR-1) is separately formed into χ=〇. 300, y=〇. 600 wins thick, coated blue photosensitive coloring The composition was χ=〇. 15〇, y=0.06G, and a green calendering fragment and a blue filter fragment were respectively formed to obtain a color filter. ^ By using the photosensitive coloring composition 2 (RR-2) ', a color filter having a high height and high contrast and no crystal precipitation in the heating step can be produced: [Example B] Parts" Unless otherwise specified, "parts" And "% by mass". "In the production of the pigment composition" is a mass of the "coloring composition", which is 323842 155 201233734, which is a diketo oxime pi-pyrrole derivative of the formula (6-3) used as a pigment derivative, and the formula (7-1) a benzoisoindole derivative, an anthracene derivative of the formula (8-5), and a quinophthalone derivative of the formula (14-1). (Average primary particle diameter of the pigment) is determined by the following method ( The average primary particle diameter of the produced pigment composition was calculated. In the powder of the pigment composition, propylene glycol monomethyl ether acetate was added, and a small amount of Disperbyk_161 as a resin type dispersant was added, and the measurement was performed by ultrasonic treatment for 1 minute. Using the sample, the sample was photographed by a penetrating (TEM) electron microscope, and three shots (3 fields of view) were used to confirm the photo of the primary particles of the ι or more pigments, and 100 samples were sequentially measured from the upper left. The size of the secondary particles. Specifically, 'the short-axis diameter and the major-axis diameter of each pigment-secondary particle are measured in units of (10), and the average particle diameter of the pigment particles is averaged as the total particle diameter of 5 nm. Distribution, (10) The central value of the scale (for example, in the case of 6 nm or more and 1 〇 nm or less, the particle diameter of these particles, the particle diameter of each particle and the number of the particles are calculated as the reference, and the number average particle diameter is calculated. <Method for Producing Diketopyrrolopyrrole Pigment Composition> [Example 1] (Production of Pigment Composition l (Rl)) In a reaction vessel made of stainless steel with a reflux tube, under a nitrogen gas loop, 200 parts of a third pentanol dehydrated by a molecular sieve and 140 parts of a third pentoxide = sodium were added, and the mixture was heated at 100 ° C while stirring to prepare an alkoxide solution. On the other hand, amber was added to a glass flask. Diisopropyl ester rib, 323842 156 201233734 4-bromobenzonitrile 153.6 parts, heated to 90 ° C while stirring to dissolve, to prepare a solution of these mixtures. The heated solution of this mixture, while stirring vigorously While spending 2 hours at a certain speed, slowly lower to 10 ° (: heating the above alkoxide solution. After the end of the drop, continue heating at 90 ° C for 2 hours to obtain a diketone ° ratio and ° A metal salt than the compound of each D compound. In a glass-lined reactor, 600 parts of decyl alcohol, 600 parts of water, and 304 parts of acetic acid were added, and the mixture was cooled to -10 ° C. The cooled mixture was mixed using a high-speed mixer. The 8 cm diameter shearing plate was rotated at 4000 rpm, and the metal salt solution obtained by cooling to 75 ° C, which was previously obtained at 25 ° C, was added in small amount. , the temperature of the mixture of decyl alcohol, acetic acid, and water is maintained at a temperature below -5 ° C, while cooling, and adjusting the addition rate of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C , added in a small amount of about 120 minutes. After the addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Next, the obtained red suspension was washed at φ 5 ° C with an ultrafiltration device, and filtered to obtain a red paste. This paste was again dispersed in 3500 parts of methanol which had been cooled to 0 ° C to prepare a suspension having a decyl alcohol concentration of about 90%. Subsequently, the mixture was stirred at 5 ° C for 3 hours, and the particles accompanying the crystal transfer were granulated and washed. The aliquot of the ketone is obtained by the pulverization of the water-soluble paste of the ketone compound at a temperature of 80 ° C for 24 hours. a brominated diketopyrrolopyrrole pigment. Next, 220 parts of the third pentanol was placed in the reaction vessel 1, and the mixture was cooled in a water bath, and 32 parts of 60% NaH was added thereto, followed by heating and stirring at 90 °C. And a compound of the following formula (B-16), which is synthesized by the method of Tetrahedron, 58 (2002) 5547 to 5565, in a reaction vessel 2, 99. 2 parts, and 60 parts of the benzonitrile compound of the formula (B4-1) was dissolved by heating, and the mixture was dropped into the reaction vessel 1 for 2 hours. After the reaction was carried out at 120 ° C for 10 hours, and then cooled to 60 ° C, 400 parts of decyl alcohol and 50 parts of acetic acid were added for filtration and decyl alcohol washing to obtain 87. 8 parts of the formula (B-2-1). Specific heterodiketopyrrolopyrrole pigment B.

Br

Further, the obtained brominated diketopyrrolopyrrole pigment of the formula (1) is 97. 0 parts of the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2-1). 3. 0 parts, 1000 parts of sodium chloride, and 120 parts of diethylene glycol were placed in a stainless steel one-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 60 ° C for 10 hours. ^ Next, the kneaded mixture is poured into warm water, heated at about 80 ° C, stirred for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at 80 ° C for one night. The average primary particle diameter is 36. 8 nm. The pigment particle composition l (Rl) of the composition of the ketone of the ketone. [Part 2] The brominated diketopyrrolopyrrole pigment of the formula (1) obtained in the production of the pigment composition 1 is 95. 0 parts, formula (B) -2-1) specific heterodiketopyrrole 323842 158 201233734 pyrrole pigment B 5. 0 parts, sodium vaporized 1000 parts, and diethylene glycol 120 parts, placed in a stainless steel 1 gallon kneader (Inoue Works In the system, knead at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, and while stirring at about 80 ° C, the mixture was stirred for 1 hour to prepare a paste, which was filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C for a day and night. 5nm。 The average particle diameter is 30. 5nm. The pigment particle composition 2 (R-2) having an average primary particle diameter of 30. 5nm. [Example 3] ® (Production of Pigment Composition 3 (R-3)), except that the brominated diketopyrrolopyrrole pigment of the formula (1) was 95. 0 parts, and the formula (B-2-1) 0份和式式式式式B(2), and the formula (B-2-1), the ketone diketopyrrolopyrrole pigment of the formula (1) is changed to 0. 0 parts, and the formula (B-2-1) And the other part is the same as the method for producing the pigment composition 2 (R-2), and 96.9 parts of the diketopyrrolopyrrole pigment is obtained. 5nm。 The average particle diameter is 26. 5nm. [Example 4] (Production of Pigment Composition 4 (R-4)) The specifics of the brominated diketopyrrolopyrrole pigment of the formula (1): 95 parts and the formula (B-2-1) a part of the heterodiketone pyrrolopyrrole pigment B 5. 0 parts, which is changed to a brominated diketopyrrolopyrrole pigment of the formula (1), 85. 0 parts, and a specific heterodione group of the formula (B-2-1) The same as the method for producing the pigment composition 2 (R-2), the same as the method for producing the pigment composition 2 (R-2), and a solution of 97. 1 part of the diketopyrrolopyrrole pigment composition is obtained. 5纳米。 The average particle diameter is 28. 5nm. [Example 5] (Production of Pigment Composition 5 (R-5)) In addition to 60.2 parts of the benzonitrile compound of the formula (B-3-1), it was changed to the carbonitrile of the formula (B-3-2). The formula (B-2-) is obtained in the same manner as in the production of the specific heterodiketopyrrolopyrrole pigment B which is carried out in the pigment composition 1 (R-1). 2) The specific heterodiketopylpolo D is shown as the pigment B of each p. • Next, the brominated diketopyrrolopyrrole pigment of the formula (1) is 95. 0 parts, the specific heterodiketone group D of the formula (B-2-2) is more than the ratio of the pigment b to each of the pigments B 5. 0 parts. 1000 parts of sodium chloride and 120 parts of diethylene glycol were placed in a stainless steel one-gallon kneader (manufactured by Inoue Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, stirred while heating at about 80 ° C for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C for a day and night by pulverization. 6纳米。 The pigment particle composition 5 (R-5) having an average primary particle diameter of 31.6 nm. [Example 6] (Production of Pigment Composition 6 (R-6)) First, except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) was changed to benzene of the formula (B-3-3) 2份的式(B-2-2) The same as the production of the specific heterodiketopyrrolopyrrole pigment B carried out in the pigment composition l (Rl), the same is obtained. 3) The specific heterodiketopyrrolopyrrole pigment B shown. 323842 160 201233734 Next, the brominated diketopyrrolopyrrole pigment of the formula (1) is 95. 0 parts, the specific heterodiketopyrrolopyrrole pigment of the formula (Β-2-3) Β 0.5 part, chlorination 1000 parts of sodium and 120 parts of diethylene glycol were placed in a stainless steel one-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, and heated at about 80 ° C, and stirred for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at 80 ° C for a day and night. 6纳米。 The granules having a particle size of 34.6 nm. [Example 7] (Production of Pigment Composition 7 (R-7)) A benzene of the formula (B-3-4a) was changed except that the benzonitrile compound of the formula (B-3-1) was 60. 2 parts. 5份的式(B-2-) The same as the production of the specific heterodiketopyrrolopyrrole pigment B carried out in the pigment composition l (Rl), the same as the production of 94.1 parts (B-2- 4a) shows the specific heterodiketopiperylpyrrolopyrrole pigment B. Next, 95.0 parts of the brominated diketopyrrolopyrrole pigment of the formula (1), the specific heterodiketopurine 17 of the formula (B-2-4a), and each of the pigments B 5. 0 parts, sodium chloride 1000 parts and 120 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, and while heating at about 80 ° C, it was mixed for 1 hour to prepare a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at 80 ° C for a day and night. 6纳米。 The granules were obtained by the pigment composition 7 (R-7), the average primary particles 323842 161 201233734 diameter was 28. 6nm. [Example 8] (Production of Pigment Composition 8 (R-8)) In addition to the specificity of the brominated diketopyrrolopyrrole pigment of the formula (1): 95 parts and the formula (B-2-4a) a heterodione-pyrrolopyrrole pigment B 5. 0 parts of a brominated diketopyrrolopyrrole pigment of the formula (1) 85. 0 parts, and a specific heterodiketopyrrole of the formula (B-2-4a) The same as the production of the pigment composition 7 (R-7), the same as the production of the pigment composition 7 (R-7), which gives 96. 1 ® parts of the diketone group and the ratio of the pyloric pigment to the composition of the pigment. 5纳米。 The average particle diameter is 25. 5nm. [Example 9] (Production of Pigment Composition 9 (R-9)) In addition to 60.2 parts of the benzoquinone compound of the formula (B-3-1), it was changed to the benzoquinone of the formula (B-3-4b). The same as the production of φ of the specific heterodiketopyrrolopyrrole pigment B carried out in the pigment composition l (Rl), the same as the compound 71. (part 1) (B-2-4b) The specific heterodiketopyrrolopyrrole pigment B is shown. Next, the brominated diketopyrrolopyrrole pigment of the formula (1) is 95. 0 parts, and the specific heterodiketone group of the formula (B-2-4b) is more than carbazide. 5.0 parts of Biro pigment B, 1000 parts of sodium carbonate, and 120 parts of diethylene glycol were placed in a stainless steel one-gallon kneader (manufactured by Inoue Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, and heated at about 80 ° C, and stirred for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at 80 ° C for a day and night. 1微米。 By pulverization to obtain 96.5 parts of the diketopipyrrole 323842 162 201233734 and pyrrole pigment composition pigment composition 9 (r_9), the average primary particle diameter is 31.1 nm. [Example 10] (Production of Pigment Composition HKR-10)

In addition to 60.2 parts of the benzonitrile compound of the formula (B-3-1), it is changed to the indole nitrile compound of the formula (B-3-5) of 49. 7 parts, and the rest with the pigment composition 1 (R- 1) The specific heterodiketone group β is produced in the same manner as in the production of each of the pigments B, and 66.9 parts of the specific heterodiketopyrrolopyrrole pigment B represented by the formula (b-2-5) is obtained. . Next, the brominated diketopyrrolopyrrole pigment of the formula (1) 95. hydrazine, the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2-5) 5. hydrazine, 1000 parts of sodium vaporized And 12 parts of diethylene glycol were placed in a stainless steel kneading kneader (manufactured by Inoue Seisakusho Co., Ltd.) at 60. (: kneading for 10 hours. Secondly, the kneaded mixture is put into warm water, and heated at about 8{rc, while stirring for summer hours to form a paste, filtered and washed with water to remove salt and diethylene glycol, at 8〇 After drying for a day and night, the pigment composition 10 (R-10) of 97. 5 parts of the bis-pyrrolopyrrole pigment composition was obtained by pulverization, and the average one was 33. lnm. [Example 11] Production of Pigment Composition ll (R-ll)) Except that the benzonitrile compound of the formula (B-3-1) 6Q. 2 parts (B=6b) of the benzonitrile compound is disordered, the rest of the blood Pigment 2 = the specific heterodiketone-based ntb-(4) domain was carried out in the same manner, and 9 〇·7 parts of the formula (B_2_6b) was obtained as the bismuth 323842 163 201233734 pyrrolopyrrole pigment B. (1) The brominated diketopyrrolopyrrole pigment 95. 0 parts, the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2-6b) 5. 0 parts, 1000 parts of sodium chloride, and two 120 parts of ethylene glycol was placed in a stainless steel one-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water. The ketone is obtained by heating at about 80 ° C, and stirring for 1 hour to form a paste. After filtering and washing with water to remove salt and diethylene glycol, drying at 80 ° C for one day and night, by pulverization, 98.1 parts of diketopyrrole is obtained. And the average primary particle diameter is 28.9%. [Example 12] (Production of Pigment Composition 12 (R-12)) In addition to the pigment composition 11 (R-11). 6 parts of the benzoquinone compound of the formula (B-3-1), changed to the benzoquinone compound of the formula (B-3-6c) 75. 6 parts, the rest with the pigment composition l (Rl The production of φ of the specific heterodiketopyrrolopyrrole pigment B carried out in the same manner is carried out, and 100. 8 parts of the specific heterodiketopyrrolopyrrole pigment B represented by the formula (B-2-6c) is obtained. (1) The brominated diketopyrrolopyrrole pigment 95. 0 parts, the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2-6c) 5. 0 parts, 1000 parts of sodium chloride, and two 120 parts of ethylene glycol was placed in a stainless steel one-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water and heated at about 80 ° C. Spoil 1 When it is made into a paste, filtered and washed with water to remove salt and diethylene glycol, dried at 80 ° C for one day and night, by pulverization to obtain 97. 4 parts of diketopyrrole 323842 164 201233734 and β specific pigment composition The pigment composition 12 (R-12) having an average primary particle diameter of 29.8 nm. [Example 13] (Production of Pigment Composition 13 (R-13)) In addition to the formula (B-3-1) 6 parts of benzonitrile compound, changed to the benzoquinone compound of formula (B-3-7) 87. 8 parts, the other specific heterodione pyrrole carried out in the pigment composition l (Rl) The production of the pyrrole pigment B was carried out in the same manner, and 85.2 parts of the specific heterodiketone group represented by the formula (B-2-7) and "Bilo pigment B" were obtained. Next, the brominated diketopyrrolopyrrole pigment of the formula (1) is 95. 0 parts, the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2-7) is 5.0 parts, and the sodium chloride is 1000 parts. 120 parts of diethylene glycol and 120 parts of diethylene glycol were placed in a stainless steel one-gallon kneader (manufactured by Inoue Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, and heated at about 80 ° C, and stirred for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at φ 80 ° C for one night. 2nm。 The pigment particle composition 13 (R-13) having an average primary particle diameter of 28. 2nm. [Example 14] (Production of Pigment Composition 14 (R-14)) In addition to the specificity of the brominated diketopyrrolopyrrole pigment of the formula (1): 95 parts and formula (B-2-7) a heterodione of the heterodiketopyrrolopyrrole pigment B 5. 0 parts, which is changed to a brominated diketopyrrolopyrrole pigment of the formula (1), 85. 0 parts, and a specific heterodione group of the formula (B-2-7) In the same manner as in the production of the pigment composition 13 (R-13), the pigment composition of the composition of the diketopyrrolopyrrole pigment composition was obtained in the same manner as in the production of the pyrrolopyrrole pigment B, 1 323. 5纳米。 The average primary particle diameter is 26. 5nm. [Example 15] (Production of Pigment Composition 15 (R-15)) In addition to 60.2 parts of the benzonitrile compound of the formula (B-3-1), the benzonitrile of the formula (B-3-8) was changed. 5份的式(B-2-8), except for the compound 50.0 parts, the same as the production of the specific heterodiketopyrrolopyrrole pigment B carried out in the pigment composition l (Rl). A specific heterodiketopyrrolopyrrole pigment B is shown. Next, the brominated diketopyrrolopyrrole pigment of the formula (1) is 95. 0 parts, 5.0 parts of the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2-8), 1000 parts of sodium chloride, and 120 parts of diethylene glycol was placed in a stainless steel 1-gallon kneader (manufactured by Inoue Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture is poured into warm water, and while stirring at a temperature of about 80 ° C, a small φ is stirred to form a paste, which is filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C for a day and night. 2nm。 The granules were obtained by the smelting. [Example 16] (Production of Pigment Composition 16 (R-16)) In a reaction vessel made of stainless steel with a reflux tube, 200 parts of a third pentanol dehydrated by molecular sieves was added under a nitrogen atmosphere, and a third 140 parts of sodium pentoxide was heated at 100 ° C while stirring to prepare an alkoxide solution. On the other hand, in a glass flask, 88 parts of diisopropyl succinate, 323842 166 201233734 4-bromobenzonitrile 146. 0 parts and a benzoquinone compound of the formula (B-3-1) 7. Six parts were dissolved by heating at 90 ° C while stirring, and a solution of these mixtures was prepared. The heated solution of the mixture was slowly dripped at a constant rate for 2 hours while vigorously stirring at 100 °C under the force of σ heat in the alkoxide solution. After the completion of the dropwise addition, heating and stirring were continued at 90 ° C for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, 600 parts of decyl alcohol, 600 parts of water, and 304 parts of acetic acid were placed in a reaction vessel in which a glass was lined with a liner, and cooled to -10 °C. The cooled mixture was rotated at a speed of 4,000 rpm while using a high-speed stirring® disperser, while the previously obtained diketone ratio of 11 was cooled to 75 ° C. A metal salt solution of a bilo compound is added in small amounts in small amounts. At this time, the temperature of the mixture of decyl alcohol, acetic acid, and water is usually an alkali metal of a diketopyrrolopyrrole compound which is cooled while being adjusted to a temperature of -5 ° C or lower and adjusted at 75 ° C. The salt addition rate was added in small portions for about 120 minutes. When the metal salt is added, red crystals are precipitated to form a red suspended φ turbid liquid. Next, the obtained red suspension was washed with an ultrafiltration apparatus at 5 ° C, and then filtered to obtain a red paste. This paste was again dispersed in 3,500 parts of sterol which had been cooled to 0 ° C to prepare a suspension having a sterol concentration of about 90 ° / Torr. Then, the mixture was stirred at 5 ° C for 3 hours, and the particles accompanying the crystal transfer were granulated and washed. Then, the water-soluble paste of the diketopyrrolopyrrole compound was dried at 80 ° C for 24 hours, and pulverized to obtain 148.1 parts of diketone ratio of 17 each. And a ratio of 11 to each pigment composition. The brominated diketopyrrolopyrrole pigment represented by the formula (1) and the specific 323842 167 201233734 represented by the formula (B-2-1) in the obtained diketone group ratio 11 and D ratio. The content of hetero-ketone-based ruthenium and ruthenium ruthenium, and the quantitative analysis of the _ _ ^ _ ketopyrrolopyrrole pigment represented by formula (1) and the formula (Β-2-1) The mass ratio of each pigment β is a dragon m HPL 曰 C measuring piece and the holding time is as follows. The necessity of L quantification &amp; 里 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋And made.瘫 device: Gulliver series detector manufactured by Sakamoto Shikotsu Co., Ltd.: UV-970 detector column made by Japan Spectrophotometer Waters a Division Symmetry ci8 (5 // m, 2· lram p xl50mm) Mobile phase A liquid: two Methyl decylamine / water (1:1) mobile phase B. dimethylformamide / water (97. 5: 2. 5) distribution (B solution): 47% ~ (15 minutes; minutes) - 1〇〇%—(25 minutes)—100%

Wavelength: 510 nm φ Column temperature: 35 ° C Flow rate: 0.3 mL/min Sample injection amount: 5 / / L (dissolved in N-methylpyrrolidone / 28% CH3 〇 Na methanol solution) The above formula (1) 0份,气。 The first time (1), the gas composition of the above-mentioned formula (B-2-1), the retention time: 13.2 to 14. 1 minutes, the obtained diketopyrrolopyrrole pigment composition 100. 0 parts, gas 1 part of sodium and 120 parts of diethylene glycol were placed in a stainless steel 1 gallon kneader (manufactured by Inoue Co., Ltd.), and 10 small 323842 168 201233734 was kneaded at 60 °C. Next, the kneaded mixture was poured into warm water, and while stirring at about 80 ° C for 1 hour, it was made into a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at 80 ° C for a day and night. 2nm。 The pigment particle composition 16 (R-16) having an average primary particle diameter of 32. 2nm. [Example 17] (Production of Pigment Composition 17 (R-17)) In a reaction vessel made of stainless steel with a reflux tube, 200 parts of a third pentanol dehydrated by molecular sieves was added under a nitrogen atmosphere®, and 140 parts of sodium tripentoxide was heated at 100 ° C while stirring to prepare an alkoxide solution. On the other hand, in a glass flask, 88 parts of diisopropyl succinate, 146.0 parts of 4-bromobenzonitrile, and 7.6 parts of a benzoquinone compound of the formula (B-3-1) were added, and while stirring, It was dissolved by heating at 90 ° C to prepare a solution of these mixtures. The heated solution of the mixture was slowly dripped at a constant rate for 2 hours at a constant rate in the above alkoxide solution φ heated at 100 °C. After the completion of the dropwise addition, heating and stirring were continued at 90 ° C for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were placed in a reaction vessel made of a glass-lined liner, and the mixture was cooled to -10 °C. The cooled mixture was rotated at 400 rpm while using a high-speed stirring disperser, and the diketone-based ratio of the pyrrole-based compound which was previously obtained by cooling to 75 ° C was rotated at 400 rpm. An alkali metal salt solution is added in small amounts. At this time, the temperature of the mixture of decyl alcohol, acetic acid, and water is maintained at a temperature of -5 ° C or lower, and while cooling, and adjusting the ketone pyrrolopyrrole compound at 75 ° C, 323842 169 201233734 alkali After the metal salt is added to the skin, the v is a salt, and the precipitate is added in a small amount by a knife. Adding a gold test to the crystal of the work, a red suspension is formed. Next, the red suspension was washed at 5, c with a super-transition device, and then transitioned to obtain a color: The paste was again dispersed until it had cooled. . . In the (10) sputum alcohol, a suspension having a methanol concentration of about _ was prepared. Then, (4) 3 hours, the particles accompanying the crystal transfer were granulated and washed. 5 Receiver's ultra-filtered, machine-based, to obtain diketone scales and simplification of the system. Further, the obtained red paste is redispersed into the paste, and after the second=10:w^m is searched for the buck, the net is obtained, and the mixture of the compound is obtained. The hourly depleted matter is broken in the 80 color pigment group 2 to 154.8 parts in the second county scale and the same as in the manufacture of the pigment composition 16 (R_16) - (4) the scale pigment composition is filled with the formula (1) The content of the 7-ketopyrrole pigment and the specific impurity = the ratio of the bromide B represented by the formula (B-2-1) is quantified by HPLC _ 2 open = pigment and formula, for example, specific poly 2 =: transfer pigment Β The mass ratio is 94.8:5·2.咏 各 _ ^ ' _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Stainless 323842. Secondly, 'mix the mixture into warm water, while: _ add 170 201233734 heat while mixing the j, when made into a paste, after simmering and washing to remove salt and diethyl alcohol, 'dry at 8 C overnight 2纳米。 By pulverization to obtain a pigment composition 17 (R-17) 'average - secondary particle diameter is 27. 2nm. [Example 18] (Production of Pigment Composition) In a reaction vessel made of stainless steel with a reflux tube, 200 parts of a third pentanol dehydrated by a molecular sieve and 140 parts of a third sodium pentoxide were added under a nitrogen atmosphere. ' While stirring, luot: heat to prepare an alkoxide solution. On the other hand, in a glass flask, 88 parts of diisopropyl succinate, 146 parts of 4-bromobenzonitrile and benzoic nitrile compound 7.6 of formula (B-3-1) were added. The mixture was heated and dissolved at 90 ° C to prepare a solution of the mixtures. The heated solution of the mixture was stirred for 2 hours while stirring vigorously, and slowly dripped at a constant rate to the above alkoxide solution heated by rc. After the completion of the dropwise addition, heating and stirring were continued at 90 ° C for 2 hours to obtain a diketone. A metal salt of a compound of each of the ratios of 17 and a ratio of 17 to a compound of a p-series. In addition, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid are added to a glass-lined reaction vessel, and cooled to - 10 ° C. This cooled mixture, using a high-speed stirring disperser, while rotating a 8 cm diameter shearing disc at 4000 rpm, while cooling it to 75 ° C, the previously obtained two g of the same base Add a small amount of the metal salt solution of the oxo-r-based compound. In this case, the temperature of the mixture of decyl alcohol, acetic acid, and water is maintained at the temperature below it: while cooling, and adjusting 75 The addition rate of the diketone-based dioxo-based compound alkali metal salt at °C was added in a small amount for about 120 minutes. After the addition of 323842 171 201233734, the red salt was precipitated to form a red suspension. Then, will get The red suspension was washed at π, super-transitioned, and filtered to obtain a red paste. The paste was again dispersed in methanol which had been cooled to the surface of the crucible to give a methanol concentration of about 9 〇. % suspension. Then, after mixing for 3 hours, the particles were granulated and washed with crystal transfer. Then, by the transition of the ultra-filter, the red paste of the two jobs was obtained. The ketone-based pyrrolopyrrole pigment composition was obtained by pulverization at 8 (TC drying for 24 hours). The formula (1) in the same procedure as in the production of the pigment composition 16 (R-16) The content of the ketones of the ketones: the ketones of the ketones and the milk-2-1) are the contents of the girders of the cockroaches. : The mass ratio of each of the pigments is 64.5:5.5. Next, the obtained diketone oxime w is different from the color of the derivative, the color of the sodium salt is 1000 parts, and the diethylene glycol 12 is 4.5 wounds. Gas-making machine (Inoue Manufacturing Co., Ltd.: t, t t (four) 1 gallon kneading mixture mixture) 2, ^ hours into a paste: water level dry one night, After the alcohol, the pigment composition 18 in the composition of: 2 [Example 19] 323842 172 201233734 (pigment composition 19CR-19)) In a stainless steel reaction vessel with a reflux tube, under a nitrogen atmosphere 200 parts of a third pentanol dehydrated by molecular sieves and 140 parts of sodium p-pentoxide were added, and the mixture was heated at 100 ° C while stirring to prepare an alkoxide solution. On the other hand, in a glass flask, 88 parts of diisopropyl succinate, 138.3 parts of 4-bromobenzonitrile, and 15.1 parts of a benzoquinone compound of the formula (B-3-1) were added. The mixture was heated and dissolved at 90 ° C while stirring to prepare a solution of these mixtures. The heated solution of this mixture was allowed to stand for 2 hours while vigorously mixing, and the solution was slowly dropped to the above alkoxide solution heated at 100 ° C at a constant rate. After the completion of the dropwise addition, the mixture was further heated and stirred at 90 ° C for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were placed in a glass-lined reaction vessel, and cooled to -10 °C. The cooled mixture was rotated at a speed of 4000 rpm while using a high-speed stirring disperser, while the previously obtained diketone π ratio of 17 was cooled to 75 ° C. The alkali metal salt solution of each of the 11 compounds was added in small amounts in small amounts. At this time, the temperature of the mixture of decyl alcohol, acetic acid, and water is usually an attempt to maintain the temperature below -5 ° C, while cooling, and while adjusting the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C The addition speed was added in a small amount for about 120 minutes. When a metal salt is added, red crystals are precipitated to form a red suspension. Next, the obtained red suspension was washed at 5 ° C with an ultrafiltration device to obtain a red paste. This paste was again dispersed in 3,500 parts of sterol which had been cooled to 0 ° C to prepare a suspension having a sterol concentration of about 90%. Subsequently, the mixture was stirred at 5 ° C for 3 hours, and the particles accompanying the crystallization transfer were granulated and washed in 323842 173 201233734. Then, the red paste of the diketope pyrrolopyrrolone compound was dried in 8 Torr for 24 hours, and 145. 8 parts of diketopyrrolopyrrole was obtained by filtration. Pigment composition: The brominated diketopyrrolopyrrole pigment of the formula (1) and the formula (B-2-) in the composition of the di-pyrrolidinopyrrole pigment are treated in the same manner as in the preparation of the pigment composition 16 (R-16). 1) The content of the specific heterodiketopyrrolopyrrole pigment B shown, when using HPIX quantitative analysis, the evolution of the steel-based pyrrolopyrrole pigment represented by formula (1) and the specific heteropoly shown in formula (B-2-1) The mass ratio of the ketopyrrole® fluorene pigment B is 88.9: 11.1. Then, 'the second granules of the squamous scales and the squamous pigments 100· 〇, 1000 parts of sodium chloride, and 12 parts of diethylene glycol were placed in a steel 1 simmering kneader (manufactured by Inoue Co., Ltd.) ), mixing 〇 〇 hours at 6 。. Next, the mixture of the mixture is put into warm water, and while the H-heat is being mixed, the (four) material is used, and the salt is washed and the salt is removed, and the ethylene glycol is removed. 8nm。 The averaging particle diameter is 28. 8nm. [Reference Example 1] (Production of Pigment Composition 20 (R-20)) The finished diketone of the formula (1) is a pigment (10). oxime, chlorine 2 1000, and monoethylene glycol 12 〇 In the case of the unrecorded steel 1 plus life*, the Inoue 1 is made in the middle of the 'mixing' for 10 hours. Secondly, the small object is poured into warm water +, - 8Gt heating on the side - while giving 1 , into a paste, and washed with water to remove salt and diethylene glycol, at 323842 174 201233734 parts of the diketone beta ratio The singularity of the pigment composition of the pigment composition of 96.6 p is 28.9 d is 38. 9 nm. [Reference Example 2] (Production of Pigment Composition 21 (R-21)) 7 parts of the desertified bismuth-pyridylpyrrolidine pigment of the formula (1), and the specific hetero formula of the formula (B-2-1) Keto group and scaly B 3q. q parts gasification

1000 parts of sodium and 120 parts of diethylene glycol were placed in a 1 gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) made of stainless steel, and mixed at 6 (TC for 1 hour). Next, the mixture was mixed. In warm water, while stirring at about 8 rc, it is made into a paste. After the water is removed and cut into diethylene glycol, it is dried at 8 ° C for one day and night, and pulverized to obtain 95 8 times. One of the ketone groups π ratio P and π ratio of the pigment composition of the pigment composition 21 (R-2 Ή, u 〇〇 ^ 'the average primary particle diameter is 28.4 nm 〇 [Reference Example 3] (Pigment composition Production of 22(R-22)) The formula (1) (four) diketone ketone and t 50 pigments, the specific hetero-diyl group of the formula (B'2-l) is converted into 1000 parts of sodium, and two 12 二醇 diol, λ 鼠 rat ^ ^ ^. Stainless steel 1 life smelting in the material ig (four). Secondly, the mixture will be mixed into the warm water, - while heating in the 咐, B, into a paste The material 'transition and washing to remove salt and &amp; °C dry-painting night' by pulverization to obtain (five) parts: = after standing at 8 [pigment pigment composition of pigment composition 22 called average 323842 175 201233734 35. 4nm [Reference Example. 4; | (a pigment composition 23 (R-23) of the manufactured)

Injecting a specific heterodiketopyrrolopyrrole pigment b 80.0 of formula (B-2-1), 1000 parts of sodium vaporized, and 110 parts of diethylene glycol into a stainless steel i-force: lun kneader (inoue In the production system, I knead for 1 hour. Its 夂' is to mix the kneaded mixture into warm water, at about 80. (: stirring while heating for 1 hour to form a paste, filtering and washing to remove salt and diethylene glycol in a 80 C drying apparatus) by pulverization to obtain 76.8 parts of diketone ratio perpyrrole pigment composition The pigment composition 23 (R-23), the average primary particle diameter is 39. 4 nm. [Reference Example 5] (Production of Pigment Composition 24 (R-24)) The deserted diketone scale of ^(1) 7 parts of each pigment, the formula of the second county and the scales (four) _ parts, gasification machine and 120 parts of diethylene glycol 'into the non-pound steel 1 plus kneading = manufactured by Inoue Manufacturing Co., Ltd.) In the _ 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混 混By pulverizing, 95.8 parts of the diketone group (tetra) and the pigment composition of the pigment composition __24) were obtained, and the average primary particle diameter was 仏3 nm. [Reference Example 6] (Production of Pigment Composition 25 (R-25)) 323842 176 201233734 Commercially available C.I. Pigment Red 254 (Irgaphor Red B-CF, 100% by Ciba Specialty Chemicals Co., Ltd.) 1 part of sodium chloride and 120 parts of diethylene glycol were placed in a stainless steel kneading kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 60 C for 10 hours. Secondly, the kneaded mixture was put into In the warm water, while stirring at a temperature of about 8 (TC) for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, dried at 8 ° C for a day and night, by pulverization to obtain 97. The pigment composition of the ketopyrrolopyrrole pigment composition is 25 (R-25), and the average primary particle diameter is 36. 3 nm. Reference [Reference Example 7] (Production of Pigment Composition 26 (R-26)) Commercially available CI Pigment Red 254 (Irgaphor RedB-CF) made by Ciba Specialty Chemicals Co., Ltd. 90.0 parts, 10.0 parts of the specific heterodiketopyrrolopyrrole pigment B of the formula (Bn), and 1 part of sodium gasification. And 120 parts of diethylene glycol were placed in a stainless steel 1 gallon kneader (manufactured by Inoue Co., Ltd.) and kneaded at 60 ° C for 10 hours. Secondly, mixed The mixture was poured into warm water. The mixture was stirred for 1 hour while heating at about 80 ° C to form a paste. After filtering and washing with water to remove salt and diethylene glycol, it was dried at 8 ° C for one day and night, and pulverized to obtain 9 5 . The pigment composition 26 (R-26) of the bis-keto-pyrrolopyrrole pigment composition having an average primary particle diameter of 31. 4 nm. The pigment composition to be produced 1 to 26 (R-1 to 26) The content is shown in Table B-1. "PR254" described in Table B-1 means C I. Pigment Red 254. 323842 177 201233734 [Table Bl] Table B1 Pigment Composition II "Pyropyrrolopyrrole Pigment pigment derivative treatment average - • Secondary particle diameter (nm) Pigment 1 Mass ratio Pigment 2 Mass ratio Salt synthesis during synthesis 贲 Example 1 R-1 Formula (1) 97 Formula (B - 2 - 1) 3 - 36. 8 Example 2 R-2 Formula (1) 95 Formula (B-2 - 1) 5 - - 30. 5 Example 3 R-3 Formula (1) 90 Formula (B-2 - 1) 10 - - 26· 5 Example 4 R-4 Formula (1) 85 Formula (B-2 - 1) 15 - - 28. 5 Example 5 R-5 Formula (1) 95 Formula (B-2-2) 5 - - 31. 6 Example 6 R-6 Formula (1) 95 Formula (B-2 - 3) 5 - - 34. 6 Example 7 R—7 Formula (1) 95 Formula (B—2_4a) 5 I— 28. 6 Poor Example 8 R-8 Formula (1) 85 Formula (B_2—4a) 15 — - 25. 5 Poor Example 9 R-9 Formula (1) 95 Formula (B-2-4-b) 5 - - 31. 1 Example 10 R-10 Formula (1) 95 Formula (B-2-5) 5 — — 33. 1 Example 11 R-11 Formula (1) 95 Formula (B_2_6b 5 — — 28. 9 Example 12 R-12 Formula (1) 95 Formula (B-2-6c) S — A 29.8 Example 13 R—13 Formula (1) 95 Formula (B-2—7) 5 — — 28. 2 Example 14 R-14 Formula (1) 85 Formula (B-2-7) 15 — — 26. 5 Example 15 R-15 Formula (1) 95 Formula (B—2-8&gt; 5 - - 34. 2 Implementation W 16 R-16 Formula (1) 94. 3 Formula (B_2-1) 5. 7 - -F 32. 2 Example 17 R-17 Formula (1) 94. 8 Formula (B-2 -1) 5. 2 Formula (7 —1) - 27. 2 Poor Example 18 R-18 Formula (1) 94. 5 Formula (B—2- 0 5. 5 - Formula (7-1) 26. 2 Example 19 R-19 Formula (1) 88. 9 Formula (Β—2—1) 11. 1 — - 28. 8 Reference Example 1 R-20 Formula (1) 100 - — - - 38. 9 Reference Example 2 R-21 Formula (1) 70 Formula (Β—2 -1) 30 - - 28. 4 Reference Example 3 R-22 Equation (1) 50 Equation (Β-2-1) 50 - - 35. 4 Reference Example 4 R-23 1 Formula (Β - 2_l) 'i 100 — — 39. 4 reference 5 R-24 Formula (1) 70 Formula (B-2-4a) j 30 - - 27. 3 Wheat test case 6 R-25 PR254 100 I— 36. 3 Reference Example 7 R-26 PR254 90 Formula (B-2 — 1) ί 10 — - 31. 4

&lt;Production method of other pigments&gt; (Production of diterpene pigment KPR177-1) 90. 0 parts of dimethicone pigment (CI Pigment Red 177), 900 parts of sodium chloride, and diethylene glycol 110 parts were placed in a stainless steel one-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 60 ° C for 10 hours. Next, the kneaded mixture was poured into warm water, stirred while heating at about 80 ° C for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C for one night. 2nm。 The pulverization to obtain 85.0 parts of the diterpene pigment KPR177-1), 178 323842 201233734 average primary particle diameter is 38. 2nm. (Production of azo pigment 1 (ΡΠ50-1)) 90 parts of azo pigment (CI Pigment Yellow 150), 900 parts of sodium vaporate, and 110 parts of diethylene glycol were placed in a gallon of stainless steel. The kneader (manufactured by Inoue Works Co., Ltd.) was kneaded at 6 ITC for 10 hours. Next, the kneaded mixture was poured into warm water, stirred while heating at about 80 ° C for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C.

2nm。 The average primary particle diameter is 26. 2nm. <Method for Producing Binder Resin Solution> (Preparation of Acrylic Resin Solution 1) A separable 4-necked flask was equipped with a thermometer, a cooling tube, a nitrogen gas inlet tube, a dropping tube, and a stirring device in a reaction vessel. Ketone 196 Known 'heating to 80 ° C ' After the reaction vessel was replaced with nitrogen, 37.2 parts of methyl methacrylate was used for the hour-by-hour, and 12 9 parts of methacrylic acid was hydroxylated by the dropping tube. Ethyl ester, 12. 〇 methacrylic acid, 2 〇. 7 parts p-cumylphenol ring

Methane-modified acrylate (ARONIX) 1. 1 wound 2' 2' _ azobisisobutyronitrile mixture was dropped. After completion/same, continue and 廄 cooling to卜~hours, and a solution of the acrylic resin is obtained. About 2 parts of the resin solution is used as a sample, and the composition is added at 180 ° C, and the resin solution of the tree is prepared in a manner of ... to make the non-volatile component 2 〇Quality 2_0 acrylic acid resin solution 1. Weight average molecular weight "W" is 323842 179 201233734 (Preparation of acrylic resin solution 2) A thermometer, a cooling tube, a nitrogen introduction tube, a dropping tube, and the like are installed in a separable 4-necked flask. In the reaction vessel of the stirring device, 207 parts of cyclohexanone was placed, and the temperature was raised to 80 ° C. After the reaction vessel was replaced with nitrogen, 20 parts of mercaptoacrylic acid and 20 parts of p-cumene were taken from the dropping tube for 2 hours. a phenol epoxide modified acrylate ("ARONIX M110" manufactured by Toagosei Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 1.33 A mixture of 2,2'-azobisisobutyronitrile was dropped. After the completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer resin solution. Next, the total amount of the copolymer solution obtained was stirred for 1 hour while injecting dry air while cooling the nitrogen gas. After cooling to room temperature, 6.5 parts of 2-mercaptopropenyloxyethyl isocyanate (Karenz, Showa Denko) Transliteration) M01), a mixture of 0.08 parts of dibutyltin laurate and 26 parts of cyclohexanone was dropped at 70 ° C for 3 hours. After the completion of the dropwise addition, the reaction was further continued for 1 hour to obtain a solution of an acrylic resin. After cooling to room temperature, about 2 parts of the resin solution was dried as a test sample at 180 ° C for 20 minutes, and then the nonvolatile matter was measured, and cyclohexanone was added to the previously synthesized resin solution to change the nonvolatile content to 20 mass. The acrylic resin solution 2 is prepared in a % manner. The weight average molecular weight (Mw) is 18,000. (Weight average molecular weight of binder resin) The weight average molecular weight of the acrylic resin is measured by GPC (gel permeation chromatography analyzer) to determine the weight average molecular weight converted into polystyrene. <Method for Producing Colored Composition Using Diketopyrrolopyrrole Pigment Composition> 323842 180 201233734 [Example 20] (Production of Colored Composition 1 (RP-1)) A mixture of the following compositions was prepared. The mixture was uniformly stirred and mixed. Using a cerium oxide ball of straight = 〇.1 coffee, it was dispersed by a pic 〇MILL grinder (manufactured by Asada Iron Works Co., Ltd.) for 8 hours, and the ruthenium film was passed through to make a coloring composition. Object l (RP-l). Diketopyrrolopyrrole pigment composition l(R-l) ii.o

Pigment derivative formula (14-1) 1 part part acrylic resin solution 1 40.0 parts of propylene glycol monodecyl ether acetate 48. 〇2 [Examples 21 to 38] (Coloring compositions 2 to i9 (RP-2 to RP- (19) Production) The coloring composition 2 to 19 was produced in the same manner as in the coloring composition 1 (RP-1) except that the pigment composition 1 (RD was changed to the pigment = product described in Table B_2). 1mm的小鍅小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小The ball was dispersed by a pico MILL grinder for 8 hours, and then filtered through a filtration membrane of m to prepare a colored composition 2 (rp-2〇). Di-pyrrolopyrrole pigment composition 丨9 (R_19) 11.0 parts of a pigment Derivative formula (6-3) 1.0 part of resin type dispersant ("BYK161" (30% solution) manufactured by Byk Chemie Co., Ltd. 6. 0 parts of acrylic resin solution 31.0 parts 323842 181 201233734 propylene glycol monoterpene ether acetate 51.0 parts [Example 40 1mm的直径。 Using a mixture of 0. 1mm The cerium oxide pellets were dispersed in a PIC〇MILL mill for 8 hours and then filtered through a 5/zm filter membrane to prepare a colored composition 2KRP-21. Diketone-pyrolopyrrole pigment composition 19 (R_19) 12.0 parts of a resin type dispersant (Ajisper PB821 manufactured by Ajinomoto FineTech Co., Ltd.) 3. 6 parts of an acrylic resin solution 1 23. 0 parts of propylene glycol monomethyl ether acetate 61.4 parts [Reference Examples 8 to 14] (Coloring) Compositions 22 to 28 (Preparation of RP-22 to 28) The same procedure as in the coloring composition IWP-D except that the pigment composition 1 (H) was changed to the pigment composition described in Table B-2 Operation, coloring compositions 22 to 28 (RP-22 to 28) were produced. 323842 182 201233734 [Table B_2] Table B-2 Colored composition Pigment composition Example 20 RP-1 R-1 Example 21 RP-2 R-2 Example 22 RP-3 R-3 Example 23 RP-4 R~4 Example 24 RP-5 R-5 Example 25 RP-6 R-6 Example 26 RP-7 R-7 Example 27 RP-8 R-8 Example 28 RP-9 R-9 Example 29 RP-10 R...10 Example 30 RP-11 R-11. Example 31 RP-12 R-12 Example 32 RP-13 R-13 Example 33 RP-14 R-14 Example 34 RP-15 R-15 Real Example 35 RP-16 R-16 Example 36 RP-17 R-17 Example 37 RP-18 R-18 Example 38 RP-19 R-19 Example 39 RP-20 R-19 Example 40 RP-21 R-19 Reference Example 8 RP-22 R-20 Reference Example 9 RP-23 R-21 Reference Example 10 RP-24 R-22 Reference Example 11 RP-25 R-23 Reference Example 12 RP-26 R-24 Reference Example 13 RP-27 R-25 Reference Example 14 RP-28 R-26

Lmm的小氧化小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小小The ball was dispersed by a PICO MILL mill for 8 hours, and then filtered through a filtration membrane of m to prepare a colored composition 29 (RP-29). 1份(色色组成物30CYP-30), a portion of a pigment derivative (8177), a portion of a pigment derivative (8-5), 1.2 parts of an acrylic resin solution, 14.0 parts of propylene glycol monoterpene ether acetate. Manufactured ® The mixture of the following composition was evenly mixed and mixed, and then pulverized with a diameter of 0. lmm, and dispersed by a PICO MILL grinder for 8 hours, 'filtered with a 5 μm filter membrane to make more Composition 30 (γρ-3〇). Azo-based pigment (ΡΥ150-1) 12. 0 parts of resin type dispersant ("6919" (50% solution) made by Byk Chemie Co., Ltd. 6.0 parts of acrylic resin solution 1 25 0 parts of propylene glycol monomethyl acetate acetate 57. 0 parts φ <Method for producing photosensitive coloring composition> [Example 41] (Production of photosensitive coloring composition) The following mixture was stirred and mixed to be uniform, and then filtered using a filtration membrane of m to prepare a photosensitive coloring composition. KRRO. Coloring composition l (RP-1) 38. 2 parts of coloring composition 29 (RP-29) 3. 8 parts of acrylic resin solution 2 13. 2 parts of photopolymerizable monomer (made by Toagosei Co., Ltd. "Α_χ _ 〇" 2. 8 parts 323842 184 201233734 Photopolymerization initiator (Irgacure-907) made by Ciba Japan Co., Ltd. 2. 0 parts of sensitizer (EAB-F, manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts of propylene glycol monoterpene ether acetate 39. 6 parts [Examples 42 to 61] (Production of photosensitive coloring compositions 2 to 21 (RR-2 to 21)) except that the coloring composition 1 (RP-1) was changed to the coloring compositions 2 to 21 ( RP-2 to 21), in addition, the ratio of the coloring compositions 2 to 21 (RP-2 to 21) to the coloring composition 29 (RP-29) is changed (in all The photosensitive coloring compositions 2 to 21 (RP-2 to 21) were produced in the same manner as in Example 41 except that the color composition was changed to 42 parts in the color ratio, and the ratio was changed in the coating film. During the evaluation, the coloring composition 2 to 21 (RP-2 to 21) and the coloring composition 29 (RP-29) were changed in such a manner that the C light source conformed to the chromaticity of χ=〇. 64〇, y=〇.328. [Reference Example 15 to 18, 20, 21] (Preparation of photosensitive color compositions 22 to 25, 27, 28 (RR-22 to 25, 27, φ 28)) In addition to the coloring composition 1 (RP) -l) changed to coloring compositions 22 to 25, 27, 28 (RR-22 to 25, 27, 28), and further, colored compositions 22 to 25, 27, 28 (RR-22 to 25, 27, 28) The photosensitive coloring composition 22 to 25, 27, 28 can be produced in the same manner as in Example 41 except that the ratio of the coloring composition 29 (rp_29) is changed (the ratio is changed within 42 parts of all the coloring compositions). (RR-22 to 25, 27, 28). Moreover, when the film is evaluated, the coloring composition 22 is changed so that the C light source χ = 640 640, y = 328. 25, 27, 28 (RP-22 25, 323 842 185 201 233 734 27, 28) and the ratio of the coloring composition 29 (RP-29) of. [Reference Example 19] (Preparation of photosensitive coloring composition 26CRR-26) The coloring composition 29 (Rp_29) was changed except that the coloring composition 1 (RP-1) was changed to the coloring composition % (RP-26). In addition, the coloring composition (YP-30) is changed, and the ratio of the coloring composition 26 (Rp to 26) to the coloring composition 3 (YP-30) is changed (the ratio is changed within 42 parts of all the coloring compositions). The rest is operated in the same manner as Shisaka 41, and the photosensitive coloring composition 26 (RR-26) can be produced. Further, when the change of the ratio is the evaluation of the coating film, the coloring group 26 (RP-26) and the coloring composition 30 (YP_3〇) are changed so that the C light source x=0.640 'y=〇.328 is the chromaticity. ratio. <Preparation and Evaluation of Coating Film Using Photosensitive Colored Composition> Using the obtained photosensitive coloring composition to the color coating film, the color characteristics and the contrast ratio were evaluated, and the evaluation of the precipitated crystal was carried out by the following method. Table B-3 shows the types and evaluation results of the coloring composition in the photosensitive coloring composition. (Evaluation of color characteristics of the coating film) The photosensitive coloring composition was applied to the glass substrate having a thickness of 100 μm x 100 mm and 0·7 μm so that the film thickness became χ=〇·640′y=〇.328. After drying, an ultraviolet ray of 3 〇〇 mJ/cm 2 was irradiated with an ultrahigh pressure mercury lamp. Further, a red coating film was obtained by heating in 230X: for 60 minutes. Thereafter, the brightness (Y) of the obtained coating film was measured by a microspectrophotometer ("Sp_Sp2" manufactured by 〇lympus Optics Co., Ltd.). Further, the chromaticity was also measured by microscopic spectrophotometry 323842 186 201233734 ("OSp-Sp2" manufactured by Olympus Optical Co., Ltd.). (Evaluation of Contrast Ratio of Coating Film) Describes the measurement method regarding the contrast ratio of the coating film. The light emitted from the backlight unit for liquid crystal display is polarized by a polarizing plate, and a dried coating film of a colored composition is applied onto the glass substrate to reach the polarizing plate. As long as the polarizing surface of the polarizing plate and the polarizing plate are parallel, although the light passes through the polarizing plate, when the polarizing surface is straight, the light is blocked by the polarizing plate. However, when the polarized light is passed through the dried coating film of the coloring composition, scattering occurs due to the pigment particles, and when one of the polarizing surfaces is staggered, the amount of light transmitted through the polarizing plate is reduced when the polarizing plates are parallel. When the polarizing plate is straight, a part of the polarizing plate passes through the polarizing plate. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance at the time when the polarizing plates were parallel and the luminance at the time of straight running (contrast ratio) was calculated. (contrast ratio) = (brightness in parallel) / (brightness in straight line) Therefore, since the pigment in the coating film is scattered, the brightness in parallel is lowered, and since the brightness during straightening increases, the contrast ratio Becomes a decline. In addition, a color luminance meter ("BM-5A" manufactured by Topco Co., Ltd.) is used as the luminance meter, and a polarizing plate ("NPF-G 122GDM" manufactured by Minto Electric Co., Ltd.) is used as the polarizing plate. The light is covered with a black mask with a 1 cm square hole in the measurement portion. X, the red color film is the same green color when the contrast ratio + is measured. (Evaluation of crystal precipitation on the surface of the coating film) 323842 187 201233734 On a glass substrate of 100 mm x 100 mm and 0.7 mm thickness, a photosensitive coloring composition is applied to a C light source so that the film thickness becomes x=0.640, and after drying, an ultrahigh pressure mercury lamp is used to irradiate 300 mJ/cm2. After the heat treatment was carried out at 230 ° C for 60 minutes, it was repeated twice at 240 ° (heat treatment for 60 minutes). The surface of the substrate coating film after the heat treatment was observed in an optical microscope, and the presence or absence of crystal precipitation was based on the following. ◎ : After heat treatment at 230 ° C for 60 minutes, further heat treatment at 240 ° C for 60 minutes, and further heat treatment at 240 ° C for 60 minutes without crystal precipitation ® 〇: 230 ° C treatment for 60 minutes heating And no further crystallization was carried out after further heating at 240 ° C for 60 minutes (the second 240 ° C heat treatment for 60 minutes showed crystal precipitation) △: no crystal precipitation after heat treatment at 230 ° C for 60 minutes, but further 240 ° C heat treatment for 60 minutes, crystal precipitation X: crystallization at 230 ° C for 60 minutes, crystal precipitation

323842 188 201233734 [Table B-3]

Table B-3 Evaluation of Pigment Dispersion in Coloring Composition Coloring Composition Results of Binding of Pyridylpyrrolopyrrole Color (Y) Contrast Ratio Crystallization Example 41 RR-1 RP-1 RP-29 21. 3 5400 0 Example 42 RR-2 RP-2 RP-29 21. 3 5600 〇 Example 43 RR-3 RP-3 RP-29 21. 0 6200 ◎ Example 44 RR-4 RP-4 RP-29 20. 8 6200 ◎ Example 45 RR-5 RP-5 RP-29 21. 2 5200 〇 Example 46 RR-6 RP-6 RP-29 21. 0 5000 〇 Example 47 RR-7 RP-7 RP-29 21. 0 6200 〇 Example 48 RR-8 RP-8 RP-29 20. 6 7000 ◎ Example 49 RR-9 RP — 9 RP-29 21. 0 5500 Appreciation Example 50 RR-10 RP-10 RP-29 21. 2 5100 〇 Example 51 RR-11 RP-11 RP-29 21. 2 5900 〇 Example 52 RR-12 RP-12 RP-29 21. 1 5500 〇贲 Example 53 RR-13 RP-13 RP -29 21. 2 5800 ◎ Example 54 RR-14 RP-14 RP-29 20. 6 6700 〇 Example 55 RR-15 RP-15 RP-29 21. 0 5000 Δ Example 56 RR-16 RP-16 RP-29 21. 2 5700 | 〇 Example 57 RR-17 RP-17 RP-29 20. 9 6200 ◎ Example 58 RR-18 RP-18 RP-29 20. 9 6300 ◎ Example 59 RR-19 RP -19 RP-29 20. 9 6000 ◎ Example 60 RR-20 RP-20 RP-29 20. 8 5800 〇 Example 61 RR-21 RP-21 RP-29 21. 3 5000 △ Reference Example 15 RR-22 RP-22 RP-29 21 3 3200 X Reference Example 16 RR-23 RP-23 RP-29 20· 2 4900 ◎ Reference Example 17 RR-24 RP-24 RP-29 19. 9 3900 ◎ Reference Example 18 RR-25 RP — 25 RP-29 19. 0 2700 ◎ Reference Example 19 RR-26 RP — 26 YP-30 19. 9 4800 ◎ Reference Example 20 RR-27 RP-27 RP-29 20. 8 1100 X Reference Example 21 RR-28 RP-28 RP- 29 20. 4 4200 △ It can be seen from the results of Table B-3 that in the formation of the color filter, the use of the brominated diketopyrrolopyrrole pigment and the specific heterodiketopyrrolopyrrole pigment B at a specific ratio ( Examples of the diketopipyrrolopyrrole pigment composition having a mass ratio of 97:3 to 85:15) are excellent in particular in terms of brightness, and further, high contrast suppresses diketopyrrole caused by the heating step And the ratio of the pigments of the 11 series of pigments precipitated. In a comparison of Example 43 with Reference Example 21, a photosensitive composition containing a brominated diketone 189 323842 201233734-based pyrrolopyrrole pigment and a specific heterodiketopyrrolopyrrole pigment B of a _ 'pyrrolopyrrole pigment composition was used. The result of the coloring composition is higher than that of the photosensitive coloring composition containing C·I. Pigment Red 254, and the high contrast is also not caused by crystal precipitation. Further, the odorized diketopyrrolopyrrole pigment which does not contain the specific heterodiketopyrrolopyrrolidinium of Example 15 is known to have excellent brightness, but has a low fresh ratio and suppresses crystallization. Further, from the results of Example 42 and Examples to 4?, and Examples 49 to 53, the effect of the specific hetero-dimethylpyrrolopyrrole pigment B was confirmed by the use of the specific hetero-network-based pyrrolopyrrole pigment B. In the examples 41 to 44 and the reference examples 15 to 18, the content ratio of the formula was slightly suppressed, and the effect of suppressing the crystallization of the kernel was increased. In addition, there is an optimum point for the comparison of 3, and if the specific impurity is suppressed, the balance of brightness and contrast can be obtained if there is a ratio of 1 base and (4). Synthetic = Γ 2 and Example 56, known as the salt granules synthesized by the number _ diacetate conjugate and the filth = domain, respectively, and the squama squama The same effect can be obtained by exemplifying the composition. Further, in the comparison of the heartbeats of the examples, it was confirmed that the same effect was obtained. (4) Knowing color silk processing is high contrast <Production of color filter> In: Green (10) 323842 #Color composition. Further, the red color is 190 201233734. The photosensitive coloring composition 16 (RR_16) of this Example B was used. (Preparation of green coloring composition 1 (GP-1)) The mixture of the following composition was mixed and mixed, and then dispersed, using a cerium oxide sphere having a diameter of 0·1 mm, dispersed by a PIC〇MILL mill. After 8 hours, it was filtered through a 5/zm filter to produce a green coloring composition 1 (GP-1).

Green pigment (CI Pigment Green 36) 6. 8 parts of yellow pigment (CI Pigment Yellow 150) 5. 2 parts of resin type dispersant (rEFKA43〇〇 made by Ciba Japan) 1.0 part of acrylic resin solution 1 30.5 parts of propylene glycol Monomethyl ether acetate 52.0 parts (Preparation of green photosensitive coloring composition 1 (GR_ 1 )) A mixture of the following composition was stirred and mixed uniformly, and then filtered with a transition film of i μα to prepare a green photosensitive coloring composition. 1 (GR_1;) 〇Green coloring composition 1 (GP-1) 42. 0 parts of acrylic resin solution 2 13. 2 parts of photopolymerizable monomer (rAR〇NIX M40〇 manufactured by Toagosei Co., Ltd.) 2. 8 parts Photopolymerization initiator (Irgacure-907) manufactured by Ciba Japan Co., Ltd. 2. 0 parts of sensitizer (EAB-F1, manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts of ethylene glycol monodecyl ether acetate 39.6 parts ( Preparation of blue coloring composition l (BP-1) The mixture of the following composition was stirred and mixed uniformly, and then dispersed in a PICO MILL mill for 8 hours using a zirconia pellet having a diameter of 〇. Filtered with a 5/zm filter to produce a blue colored composition 1 323842 191 201233734 (ΒΡ-l) 7. 2 parts 4. 8 parts 1. 0 parts 35. 52 part 52. 蓝色part blue pigment (C·I. Pigment Blue 15 : 6) Purple pigment (CI Pigment Violet 23) Resin type dispersant ("EFKA4300" manufactured by Ciba Japan Co., Ltd.) Acrylic resin solution 1 Propylene glycol monodecyl ether acetate (modulation of blue photosensitive coloring composition)

The mixture of the following composition was stirred and mixed uniformly, and then filtered through a filter membrane of 丨 &quot; to prepare a blue photosensitive coloring composition 1 (BR 〇 34. 〇: 15: 2 parts 3 · 3 parts 0 parts 〇 - 4 parts of blue coloring composition 1 (BP-1) Acrylic resin solution 2 Photopolymerizable monomer ("Ar〇nIX M400" manufactured by Toagosei Co., Ltd.) Photopolymerization initiator (rIrgacure_9〇7, manufactured by Ciba Japan) A sensitizer ("EAB-F1" ethylene glycol monomethyl ether acetate π manufactured by Hodogaya Chemical Co., Ltd.), a black matrix pattern was processed on a glass substrate, and a photosensitive coloring composition was spin-coated on the substrate. L6 (RR_l6) is applied to form a colored film by the film thickness of 〇 . . . 〇 328. The film is irradiated with ultraviolet rays of 3 〇〇 mJ/cm 2 using an ultrahigh pressure mercury lamp through a mask. The unexposed portion was removed by spray development with an alkaline developing solution of 0.2% by weight aqueous sodium carbonate solution, and then washed with ion-exchanged water, and the substrate was heated at 23 ° C for 20 minutes to form a red color. Filtered fragments. By the same method, green photosensitive is applied separately The composition l (GR-1) was set to x=0. 300, y=0. 600 film thickness 'coated blue photosensitive coloring composition KBR-丨) into χ=〇15〇, 323842 192 201233734 y=0 The film thickness of 060 forms a green filter segment and a blue filter segment to obtain a color filter. By using the photosensitive coloring composition 16 (RR_i6), high brightness and high contrast can be produced, and heating is performed. In the step C, the "parts" and "%" represent "mass parts" and "% by mass", respectively. The specific surface area, the primary particle diameter of the pigment, the weight average molecular weight (Mw) of the resin, the acid value of the resin, and the contrast ratio (CR) of the zero coating film are measured as follows. (Specific surface area of the pigment) Ratio of the pigment particles The surface area was determined by the BET method of adsorbing nitrogen gas. In the measurement, an automatic vapor adsorption amount measuring device ("BELS0RP18" manufactured by Beckham Co., Ltd.) was used. (Average primary particle diameter of the pigment) Average primary particle of the pigment The diameter is directly measured by electron micrographs. Specifically, the short axis diameter and the major axis diameter of the primary particles of each pigment are measured, and the average is taken as the particle diameter of the pigment particles. Next, regarding one or more pigment particles, The volume average particle diameter was determined as the average primary particle diameter by approximating the volume (weight) of each particle to the obtained particle size cube, and the electron microscope was a transmission type (TEM). Molecular weight (MW)) A TSKgel column (manufactured by TOHSO Co., Ltd.) equipped with a R] detector GPCCT0HS0 company's "HLC-8120GPC" was used, and THF was used as a solvent for the development of 323842 193 201233734, and the weight average converted to polystyrene was measured. Molecular weight (Mw). (acid value of resin) In the resin solution 0.5 to lg 'add acetone 8 〇mi and water 10 ml. Stir and dissolve to dissolve, use 〇· lm〇l / L Κ 0 Η aqueous solution as a titrant, use automatic The titration device ("C0M_555", manufactured by Hiranuma Sangyo Co., Ltd.) was titrated to measure the acid value of the resin solution. Thus, the equivalent acid value of the resin solid content was calculated from the acid value of the resin solution and the solid content concentration of the resin solution. (Contrast Ratio of Coating Film) The light emitted from the liquid crystal display backlight unit is polarized by a polarizing plate. A dry coating film of a coloring composition is applied onto a glass substrate to reach a polarizing plate. As long as the polarizing surfaces of the polarizing plate and the polarizing plate are parallel, the light passes through the polarizing plate, but when the polarizing surface is straight, the light is blocked by the polarizing plate. However, when the polarized light passes through the dried coating film of the colored composition by the polarizing plate, 'scattering due to the pigment particles, etc., when one of the polarizing surfaces is staggered, the amount of light penetrating the polarizing plate when the polarizing plates are parallel Will reduce 'a part of the light will penetrate the polarizer when the polarizer is straight. This transmitted light was used as the luminance on the polarizing plate, and the ratio of the luminance at the time when the polarizing plates were parallel and the luminance at the time of straight running (contrast ratio) was calculated. (brightness when the contrast ratio is parallel) / (brightness when going straight) and "using a color luminance meter ("BM-5A" manufactured by Topco Corporation) as a brightness meter" is a polarizing plate (made by Nitto Denko Corporation) NPF-G1220DUN". In order to block excess light during measurement, a black mask with a 1cm square hole is placed on the measurement portion. Before the embodiment, the adhesions used in the examples and reference examples will be described. 323842 194 201233734 Resin (B) solution, pigment (A1, micronized pigment, and method for producing pigment dispersion). (Manufacturing method of binder resin (B) solution> [Soluble-sensitive resin (B1-1) )] Put a ring of dog food into a separable four-mouthed view with a thermometer, a cooling tube, a nitrogen inlet tube, and a spoiler, and heat up to 8 〇. (: After replacing the flask with nitrogen, borrow 18 parts of p-isopropylphenyl oxime Ethylene Ethylene was changed from the dropping tube to the time of 2 hours (4) (East Asia Synthetic (share) Pang Si "face IX M110", 10 parts of methyl acyl benzoate , μ part of thioglycolic acid glycidol vinegar, 25 A mixture of 2,2'-azobisisobutyronitrile of thiol (iv) acid and 2 parts of azobisisobutyronitrile was added dropwise. After dropping, it was further reacted at ι ° ° C for 3 hours, and then dissolved in 50 parts of cyclohexene. 1 〇 solution of azobisisobutyronitrile was further reacted at 100 ° C for 1 hour. Then, replacing the inside of the vessel with air 'will be 0.5 part of 9.3 parts (glycidyl equivalent) of acrylic acid The dinonylamino group and 0.1 part of hydrogen are put into the above container, and φ is continuously reacted for 6 hours at 120, and when it becomes a solid acid value of 0.5, the reaction is terminated to obtain a solution of the acrylic acid resin. 19 parts of tetrahydro succinic anhydride (equivalent of the resulting hydroxyl group), triethylamine 0 5 parts, and reacted at 120 ° C for 3.5 hours to obtain a solution of acrylic resin. After cooling to room temperature, the resin About 2 g of the solution was heated and dried for 20 minutes on a crucible, and the nonvolatile matter was measured. In the previously synthesized resin solution, PGMEA was added in an attempt to change the nonvolatile content to 20% by weight to obtain an insoluble soluble photosensitive resin ( B1 -1) solution. The weight average molecular weight (Mw) is 19000 〇323842 195 201233 734 [Acrylic Resin Solution 1] In a reaction vessel, 370 parts of % hexane was placed in a container, and while nitrogen gas was injected, it was heated in 80 C, and at the same temperature, 20. methacrylic acid, 10.0 parts of methacrylic acid was added. Ester, 55.0 parts of 11-butyl methacrylate, 15.0 parts of 2-light-ethyl decyl acrylate, 4. 〇 2, 2, _ azobisisobutyronitrile mixture for 1 hour The polymerization was carried out by dropping. After the completion of the dropwise addition, the reaction was further continued at 80 C for 3 hours, and then a solution of 1 part of azobisisobutyronitrile was dissolved in 5 parts of cyclohexan, and the reaction was continued at 8 (TC). 1 hour, while ® gets an acrylic resin solution. After cooling to room temperature, about 2 g of the resin solution was dried as a sample in i8 ° C for 20 minutes, and then the nonvolatile matter was measured. In the previously synthesized resin solution, cyclohexanone was added in an attempt to change the nonvolatile content into 2 The acrylic resin solution 1 was obtained by 5% by weight. The weight average molecular weight (Mw) is 4 Å. <Method for Producing Pigment (A1) Formula (1)> First, in a stainless steel reaction vessel with a return pipe,

Under the environment, the third sterol fraction dehydrated by the molecular sieve and the third pentoxide and the sodium oxyhydroxide 140 parts of the side-side sandalwood were heated at 1Q and heated to prepare an alkoxide solution. On the other hand, in a glass flask, a solution of bismuth diacetate (10) and 153.6 parts of 4-dibenzoquinone were added, and while stirring, the solution of the conjugate was spread. The mixture was mixed with the dance solution and stirred vigorously for 2 hours at a constant rate to the above alkoxide solution heated in ion: heating. After the completion of the dropping, the heating was continued for 2 hours in the order to obtain the metal salt of the compound. In the step-by-step process, add 323842 196 201233734 to 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid, and cool to a temperature of 10 °C. The cooled mixture was rotated at 4 rpm while using a high-speed stirring disperser, while the previously obtained diketopyrrolopyrrole cooled to 75 C was cooled therein. Alkali metal salt of compound

The solution was added in small amounts. At this time, the temperature of the mixture made of methanol, acetic acid, and water is continuously maintained at a temperature of -5 ° C or lower, while cooling, and while adjusting the metal salt of 75 C of the dimercapto group The addition speed was added in a small amount for about 120 minutes. When a metal salt is added, a red crystal precipitates to form a red suspension. Next, the obtained red suspension was washed in the rhyme apparatus, and (4) (iv) a red paste. This paste was again dispersed in 35 liters of sterol which had been cooled to 〇, to prepare a suspension having a methanol concentration of about 90%. Then, at 5. The crucible was stirred for 3 hours, and the particles accompanying the crystal transfer were granulated and washed. Next, an ultra-filter is used to obtain a water-based paste of a bis-base compound and a lanthanide compound, which is dried at 8 (TC for 24 hours, and 15 y·8 parts of the pigment (A1) represented by the formula (1) is obtained by pulverization. Brominated diketopyrrolopyrrole pigment 5. [BDE diketopyrrolopyrrole pigment (A1-1)] 100.0 parts of the deserted diketone scale and each pigment b of the sodium chloride, and two 12G of ethylene glycol, put in stainless steel ^ plus kneading machine (made by Inoue Manufacturing Co., Ltd.), mixing 2 small in the ah. Secondly, the mixture is mixed into warm water, while about 8 〇. The paper was heated - stirred for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol. After drying - painting night, 96.5 parts of the formula (1) of the deserted diketone scale was prepared. Scale 赖 UH), the average - chemical diameter is 65 dragons, than 323842 197 201233734 surface area is 30m2 / g. [Bromide diketopyrrolopyrrole pigment (A1-2)] 100. 0 parts of desertified diketone n is more than 11 moles of pigment, 1, 1000 parts of sodium chloride, and 120 parts of diethylene The alcohol was placed in a stainless steel one gallon kneader (manufactured by Inoue Co., Ltd.) and kneaded at 60 ° C for 4 hours. Next, the kneaded mixture was poured into warm water, stirred while heating at about 80 ° C for 1 hour to form a paste, filtered and washed with water to remove salt and diethylene glycol, and dried at 80 ° C for one night. 96.6 parts of each of the brominated diketopyrrolopyrrole p pigments (A1-2) having an average primary particle diameter of 55 nm and a specific surface area of 45 m 2 /g 〇 [brominated diketone group. More than arropyrrole pigment (A1 - 3 )] 100 parts of brominated diketopyrrolopyrrole pigment 1, 1000 parts of sodium sulphate, and 120 parts of diethylene glycol, 1 gallon in stainless steel In a kneading machine (manufactured by Inoue Seisakusho Co., Ltd.), 6 (TC was kneaded for 8 hours. Secondly, the kneaded mixture was poured into warm water, and while stirring at a temperature of about 80 ° C, a small φ was stirred to prepare a paste, which was filtered and washed. After removing salt and diethylene glycol, drying at 80 ° C for one day and night, by pulverization, 95.6 parts of brominated diketopyrrolopyrrole pigment (A b 3), the average primary particle diameter is 38 nm, specific surface area Is 80 m2 / g ° [brominated diketone ° pyrrole pigment (A1-4)] 100. 0 parts of brominated diketopyrrolopyrrole pigment 1, 1000 parts of sodium, and 120 The diethylene glycol was placed in a stainless steel one-gallon kneader (manufactured by Inoue Co., Ltd.) and kneaded at 60 ° C for 12 hours. Next, the kneaded mixture was poured into warm water while heating at about 80 ° C. Stir 1 323842 198 201233734 hours to make a paste 'filtered and washed to remove salt and diethylene glycol, then dry at 80 C for a day and night, From the pulverization, 96.2 parts of the brominated diketopyrrole were used to give a pigment (A1-4), and the average-secondary particle diameter was 3 〇 nm, and the specific surface area was 120 m 2 /g. [Dicarbonyl ketone bromide] And 吼 颜料 pigment (A 卜 5)] 100. 0 parts of brominated diketopyrrolopyrrole pigment 丨, 1 part of sodium hydride, and 12 parts of diethylene glycol, not put In a steel i-gallon kneading machine (manufactured by Inoue Seisakusho Co., Ltd.), it was kneaded at 6 (TC for 24 hours. Secondly, the kneaded mixture was poured into warm water, and stirred at about 8 (TC was heated for 1 hour to make a paste). After filtration, washing with water and removing the salt and diethylene glycol, drying at 100 ° C, and pulverizing to obtain 96.2 parts of the brominated diketone group to open the pigment (A1-5). The average primary particle diameter is 19 nm, and the specific surface area is 180 m 2 /g. [Bromide diketopyrrolopyrrole pigment (A1_6)] 100. 0 parts of brominated diketone group" is slightly mixed with each pigment 1 ' 1000 The sodium chloride and 120 parts of ethylene glycol are placed in a non-recorded steel j-plus kneader (manufactured by Inoue Seisakusho Co., Ltd.), and (10) it is mixed for hours. Secondly, the mixture will be mixed. Into warm water, while stirring, oh, heating, stirring, smashing, sifting, washing and removing salt and diethylene glycol, drying at 8 ° C, and pulverizing to obtain 96. 2 parts The brominated diketone pi-pyrrolopyrrole pigment (A1_6) has an average primary particle diameter of 9 (10) and a specific surface area of 270 m 2 /g. The produced brominated diketopyrrolopyrrole pigment (A 丨 to 6) The contents are shown in Table C-1. 323842 199 201233734 [Table C1] Table Cl Desertified diketone valence and β ratio π each pigment A1-1 A1-2 A1-3 A1-4 A1-5 A1-6 Mixing time (hours) 2 4 8 12 24 48 Average primary particle diameter (nm) 65 55 38 30 19 9 Specific surface area (m2/g) 30 45 80 120 180 270 <Method for producing pigment dispersion> φ [Pigment dispersion] (P-1)] After the mixture of the following composition was stirred and mixed uniformly, a disulfide pellet having a diameter of 1 mm was used, and after dispersing for 5 hours in an Eiger mill ("Mini mode 1 M-250 MK11" manufactured by Eiger Japan Co., Ltd.) The red pigment dispersion (P-1) was obtained by passing through a ruthenium film of 5 // m. Brominated diketopyrrolopyrrole pigment (A1-1) 8. 78 parts of acidic resin type pigment dispersant 1.74 parts (BYK-111 manufactured by Byk Chemie Japan) ® Diketopylbibilol ratio Derivatives 2. 05 derivatives 1

5· 83 parts of acrylic resin solution 1 323842 200 201233734 81. 60 parts [pigment dispersion (P-2)] In addition to changing the evolution of the diketone β to argon and η than the P pigment (A 1 _ 1 ) changed to desertification The monoketone "» is similar to the respective pigments (ai-2), and the rest is operated in the same manner as the red pigment dispersion (Ρ-1) to obtain a red pigment dispersion (Ρ_2). [Pigment Dispersion (Ρ-3)] In addition to changing the brominated diketone group V» than the pyrrole pyrrole pigment (Astragalus) to the brominated diketopyrrolopyrrole pigment (Α3) The red pigment dispersion (Ρ-1) was also operated to give a red pigment dispersion (ρ_3). [Pigment Dispersion (Ρ-4)] In addition to changing the brominated diketopyrrolopyrrole pigment (Ai-i) to the brominated diketopyrrolopyrrole pigment (Α1-4), the remaining red pigment The dispersion (Ρ-1) was operated in the same manner to obtain a red pigment dispersion (p_R4). [Pigment Dispersion (P-5)] In addition to changing the brominated diketopyrrolopyrrole pigment (A 丨) to a bromine Φ 一 基 基 ° ° ° 各 each pyrrole pigment (A1-5), The rest is treated in the same manner as the red pigment dispersion (P_1) to obtain a red pigment dispersion (P-5) » [Pigment dispersion (P-6)] In addition to changing the deserted diketopyrrolopyrrole pigment (A1_i) to bromine The first line of the syllabus The red pigment dispersion (p_6) was obtained in the same manner as the red pigment dispersion (P-1) except for the specific pigment (M_6).

[Pigment Dispersion (P-7) J In addition to changing the filled diketopyrrolopyrrole pigment (Eight Buddhism) to a chlorinated bifido-pyrolopyrrole pigment (CI Pigment Red 254; Ciba Japan 323842 The red pigment dispersion (P-7) was obtained in the same manner as in the red pigment dispersion (P-1) except for "Irgaphor Red B-CF" manufactured by 201, 2012,734. [Pigment Dispersion (P-8)] After mixing and mixing the following composition mixture, an Eiger mill ("Mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) was used as an Eiger mill using a diameter of 1 mm. After an hour, it was filtered with a 5#πι filter membrane to obtain a pigment dispersion (Ρ-8).

Brominated diketopyrrolopyrrole pigment (Α3) 6. 82 parts of anthraquinone pigment (C.I·Pigment Red 177) 1. 08 parts (Cromophthal Red Α2Β made by Ciba Japan) Nickel azo Compound pigment (CI Pigment Yellow 150) 0. 88 parts (rE4GN manufactured by Lanxess Co., Ltd.) 1. Resin-based pigment dispersant 1.74 parts ("s〇lsperse 21000" manufactured by Lubrizol Co., Ltd.) Pigment Derivative 1 2. 05 Derivative 1

5. 83 parts 81.60 parts of acrylic resin solution 1 cyclohexanone 323842 202 201233734 [Pigment dispersion (P-9 to 20)] except for the pigments, pigment derivatives, and resin type pigment dispersants shown in Table C-2 The type of the mixture and the amount of the mixture were the same as those of the pigment dispersion (P-8) to obtain a pigment dispersion (P-9 to 20). [Table C-2] Table C-2 Pigment Dispersion Pigment 1 Pigment 2 Pigment 3 Pigment Derivative Parts Partition P-8 A1-3 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P—9 A1 — 1 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P-10 A1—2 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P-11 A1-4 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P—12 A1-5 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P-13 A1-6 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P-14 PR254 6.50 PR177 1.23 PY150 1.05 Derivative 1 2.05 P-15 A1-3 7.07 P071 0.93 PY150 0.7B Derivative 1 2.05 P-16 A1- 3 7.34 PR242 0J9 PY150 0.45 Derivative 1 2.05 P-17 A1-3 6.79 PR179 1.09 PY150 0.90 2.05 P-18 A1-3 6.73 PR122 0.85 PY150 1.20 2.05 P —19 A1-3 6.75 1.10 PY180 0.93 Derivative 4 2.05 P- 20 A1—3 7.17 1.61 - Derivatives 1 2.05

The abbreviations in Table C-2 are as follows. <Pigment> φ PR254 : Diketopyrrolopyrrole pigment CI Pigment Red 254; "Irgaphor Red B-CF" manufactured by Ciba Japan Co., Ltd. P071: Diketopyrrolopyrrole pigment CI Pigment Orange 71; Ciba Japan "Irgazin DPP 0range398" PR242: azo pigment CI Pigment Red 242; "N0V0PERM" manufactured by Clariant Co., Ltd. PR179: lanthanide pigment CI Pigment Red 179; Dainippon Ink Chemical Industry Co., Ltd. "Fastogen $uper MaroonPSK" PR122 : quinacridone pigment CI Pigment Red 122; 203 323842 201233734 "HOSTAPERM" PY180: benzimidazolone pigment CI Pigment Yellow 180; "PV First Yellow HG" manufactured by Clariant Co., Ltd. PY138: Quinoline pigment CI pigment Yellow 180; "Paliotol Yellow K0960-HD" manufactured by BASF Corporation <Pigment Derivatives> Derivatives 2

201233734 Derivative 4

[Example 1] (Red coloring composition (DR-1)) The following composition mixture was stirred and mixed uniformly, and then filtered through an over-concentrated membrane of 5 μm to obtain a red colored composition (DR-1). Red pigment dispersion (P-1) 40. 5 parts alkali-soluble photosensitive resin (B1-1) 8. 6 parts cyclohexanone 50. 9 parts [Examples 2 to 6 and Reference Example 1] φ (red coloring composition) (DR-2 to 7)) In addition to changing the red pigment dispersion (P-I) to the red pigment dispersion shown in Table C-3, the same operation as the red coloring composition (Dr_1) was performed to obtain red coloration. Composition (DR-2 to 7)). [Reference Example 2] (Red coloring composition (DR-8)) The same as the red coloring composition (3), except that the alkali-soluble photosensitive resin (B丨_丨) was changed to the acrylic resin solution 1. Operation gave a red colored composition (DR-8). 323842 205 201233734 [Evaluation of Red Colored Composition] The color characteristics, the contrast ratio (CR) of the obtained red colored composition, and the crystallization of the surface of the coating film were evaluated by the following methods. The results are shown in Table C-3. (Color characteristic, contrast ratio (CR) evaluation) The red colored composition was applied to a glass substrate having a thickness of 10Omm X 10Omm and 0.7 mm, and the C light source was used to make the film thickness x = 0. y = 0 340 It is applied in the way of the 正. &lt;: After drying in a hot air oven for 20 minutes, it was further heated at 23 Torr for 6 minutes to obtain a red coating film. Thereafter, the brightness (γ) of the coated substrate and the contrast ratio (CR) were measured. Further, the chromaticity and the luminance (γ) were measured by a microspectrophotometer ("OSP-SP200" manufactured by 〇lympus Optics Co., Ltd.). (Evaluation of crystal precipitation on the surface of the coating film) The substrate obtained by evaluation of color characteristics and contrast ratio (CR) was repeated.

2 times at 240 ° C heating ί 里 60 minutes. The surface of the coating film of the coated substrate after the heat treatment was observed by an optical microscope, and the presence or absence of precipitation was determined according to the following criteria. In the evaluation results, ◎ and 〇 are not crystallized, and the crystallization is good, but there is no problem in the crystallization, and the crystallization is because the crystallization is equivalent to an unusable state. ◎ : 23 (TC heat treatment for 60 minutes, after the step of 2 weeks of twisting treatment for 60 minutes, and then heat treatment at 240 ° C for 6 minutes, also after the heat treatment for 6G minutes, and then further It is also known that no crystals are precipitated (the second 24 "c heat treatment for 6 minutes has 323842 206 201233734 crystal precipitation" △: no crystal precipitation after heat treatment at 230 ° C for 60 minutes, but further 240 ° C heat treatment 60 Crystallization precipitated in minutes: Crystallization occurred after heat treatment at 230 ° C for 60 minutes [Table C-3] Table C-3

Red coloring composition Red pigment dispersion Brightness (Y) CR Crystal precipitation Example 1 DR-1 P-1 23.33 9000 ◎ Example 2 DR-2 P-2 23.27 12000 ◎ Example 3 DR-3 P-3 23.26 13000 ◎ Example 4 DR-4 P-4 23.23 12000 ◎ Example 5 DR-5 P-5 23.22 11000 ◎ Example 6 DR-6 P-6 23.23 9000 ◎ Reference Example 1 DR-7 P-7 20.83 6000 X Reference Example 2 DR-8 P-1 21.06 6000 X

A coloring composition for a color filter containing the pigment (A1) represented by the formula (1) and the alkali-soluble photosensitive resin (B1), which is high in brightness and high in contrast ratio, does not occur even in a heating step Good results were obtained by precipitating the crystals of the pigments of the pigments of the two bases, 11 bases, and the like. [Examples 7 to 41, Reference Examples 3 to 5] (Photosensitive Coloring Composition) The compositions shown in Tables C-4 to C-9 were mixed and stirred in a blending amount, and filtered at 1 #m. The membrane was filtered to obtain a photosensitive coloring composition. 323842 207 201233734 [Table C-4] Wrap C-4 Embodiment 7 Example 8 Example 9 Example 10 Example 11 Implementation 洌*12 Reward 13 RR-1 RR-2 RR-3 RR-4 RR- 5 RR-6 RR-7 pigment dispersion 逋P-8 P-8 P-8 P-8 P-8 P-8 P-8 41.92 37.53 23.64 42.91 17.73 31.55 31.93 Acrylic resin solution 1 14.85 15.25 35.09 18.60 28.27 28.70 27.33 Alkali Soluble photosensitive resin (B1 - 1) 10.00 10.00 10.00 10.00 10.00 10.00 10.00 Photopolymerization initiator (D) D1 D1 01 D1 D1 D1 D1 0.52 0.53 0.45 0.50 0.95 0.85 0.67 D2 D2 D2 D4 D2 D2 0.13 0.45 0.25 0.20 0.30 0.10 D3 03 0.28 0.25 Sensitization (E) E1 E2 0.25 0.05 Photopolymerizable compound 1.74 1.32 2.81 1.25 5.07 2.96 1.34 Multi-manganese mercaptan (Π F1 0.60 UV absorption (G> G1 0.28 Organic spray 30.97 35.24 27.28 25.99 37.18 25 .(10) 28.35 Total 100.00 100.00 100.00 100.00 100.00 100.00 100.00

[Table C-5] Table C-5 Example 14 Example 15 Example 16 Example 17 Example 18 Example 19 Example 20 RR-8 RR-9 RR-10 RR-11 RR-12 RR- 13 RR-14 pigment dispersion 逋P-8 P-8 P-8 P»8 P-8 P-8 P-8 40.60 34.96 38.57 42.10 42.78 27.69 34.82 Acrylic tree solution 1 tO.77 18.00 id.te 2.54 3.99 32.40 31.56 Alkali-soluble photosensitive resin (B1—1) 10.00 10.00 10.00 10.00 10.00 10.00 10.00 Photopolymerization initiator (D) D3 D3 D3 D3 D3 Del D3 1.40 1.45 0.73 0.70 0.48 0.3» 0.21 D2 D5 D2 OZ 02 0.43 0.11 0.43 0.2 » 0.09 D4 0.40 增 Thanks (E) E2 0.2t photopolymerizable compound 2.28 1.54 1.45 2.34 1.18 3.34 1.02 poly-sterol (F) F2 0.30 polymerization inhibitor (H) HI H2 0.01 0.01 organic solvent 34.73 34.05 29.64 42.21 40.74 25.70 22.00 Total 100.00 100.00 100.00 100.00 100.00 100.00 100.00 208 323842 201233734 [Table C-6] jfec-β Example 21 Example 22 Example 23 Example 24 Example 25 Example 26 Example 27 RR-15 RR -16 RR-17 RR-18 RR-19 RR-.20 RR-21 Dispersion wanted P-8 P-8 P-8 P-8 P-8 P-8 P-8 24.46 20.13 37.11 21.13 21.44 26.98 42.79 Acrylic resin solution 1 26.51 27.76 0.00 24.41 4.93 4.41 0.00 Alkali-soluble photosensitive resin (B* ( — 1) 10.00 to.oo 10.00 10.00 10.00 10.00 10.00 Photopolymerization initiator (D) D4 D4 D4 D4 D4 D4 D4 0.60 1.08 2.74 3.31 093 3.44 1.41 DS D5 D5 D5 D5 0.12 0.05 0.24 0.61 1.15 D3 0.17 Sensitizer (E&gt; E1 E2 E1 1.03 0.15 0,09 First polymerizable compound 2.03 4.30 2.93 6.62 3.12 4.53 2.40 UV absorber (G) G2 0.10 安藏安定射 (J&gt; J1 J2: 0.03 0.0:) Organic solvent 36.25 36.68 46.19 34.14 58.61 50.55 42.25 Total 100.00 100.00 100.00 100.00 100.00 100.00 100.00

[Table C-7] Example 2 β Example 29 Example 30 Example 31 Example 32 Example 33 Example 34 RR-22 RR-23 RR-24 RR-25 RR—26 RR-27 RR-28 Pigment dispersion P-8 pa P-8 P-9 P-10 P-11 P- 12 43.14 35.73 35.26 41.92 41.92 41.92! 41.92 Acrylic resin solution 1 3.55 1.02 0.00 14.85 14.85 14.85 14.85 Alkali-soluble photosensitive resin [B1 — 1) 10.00 10.00 10.00 10.00 10.00 10.00 10.00 Photopolymerization initiator (D) 01 01 Dt 01 D1 D1 D1 1.62 1.44 0.94 0.52 0.52 0.52 0.52 D3 D3 0.40 0.24 Sensitization (E) E2 0.40 Photopolymerization compound 2.68 1.60 1.28 1.74 1.74 1.74 1.74 Multi-manganese mercaptan (F) F2 F3 0.74 0.50 Polymerization prohibition (H) Organic dissolution profile 38.21 49.47 51.78 30.97 30.97 30.97 30.97 Total 100.00 100.00 100.00 100.00 100.00 100.00 too.oo 209 323842 201233734 [Table C_8] Table C-8 Example 35 Example 36 Example 37 Lean Example 38 Example 39 Example 40 Example 41 RR-29 RR-30 RR-31 RR-32 RR-33 RR--34 RR-35 Pigment Dispersion P -13 P-15 P-16 P-17 P —18 P-19 P-20 41.92 41.92 41.92 41.92 41.92 41.52 41.92 Acrylic resin solution 1 14.85 14.85 14.85 14.85 14.85 14.85 14.85 Alkali-soluble photosensitive resin (B1 — 10.00 10.00 10.00 10.00 10.00 10.00 10.00 Photopolymerization start 剤 (D) D1 D1 D1 DY 01 D1 01 0.52 0.52 0.52 0.52 0.52 0.52 0.52 Sensitizer (E) Photopolymerizable compound 1.74 1.74 1.74 1.74 1.74 1.74 1.74 Multi-functional thiol (F) Polymeric inhibitor 〇〇 Organic solvent 30.97 30.97 30.97 30.97 30.97 30.&lt;»7 30.97 and ¥100.00 100.00 100.00 100.00 100.00 100.00 100.00

[Table C_9] Table C-9

Reference Example 3 Reference Example 4 Reference Example 5 RR-36 RR-37 RR-38 Pigment dispersion P-14 P-14 P-3 41.92 41.92 41.92 Acrylic resin solvent 1. 14.85 24.85 24.85 Alkali-soluble photosensitive resin ΪΒ1 —1) 10.00 D1 D1 D1 0.52 0.52 0.52 Photopolymerization initiator (D) Sensitizer (E) Photopolymerizable compound 1.74 1.74 1.74 Polyfunctional thiol (F) Polymerization inhibitor (H) Organic solvent 30.97 30.97 30.97 Total 100.00 100.00 ί 00.00 The abbreviations in Tables C-4 to C-9 are indicated below. <Photopolymerization initiator (D)> 210 323842 201233734 Photopolymerization initiator D1: 2-mercapto-l-[4-(methylthio)phenyl]-2-morpholinium -1--, (Irgacure 9〇7, manufactured by Ciba Japan) Photopolymerization initiator D2: 2-(didecylamino)-2-[(4-methylphenyl)indolyl]-l-[4- (4-morpholinyl)phenyl]-ι-butanone; (Irgacure 379, manufactured by Ciba Japan Co., Ltd.) Photopolymerization initiator D3: Ethyl-1-ketone, i-[9-ethyl-6 -(2-mercaptobenzoyl)-9H-carbazol-3-yl], 1-(anthracene-ethene); ("Irgacure 0ΧΕ 02", manufactured by Ciba") Photopolymerization initiator D4: 2, 2,-bis(〇-chlorophenyl)-4, 5,4,,5,-tetraphenyl-1,2-linked beta-saliva; ("Golden Chemicals" company "Lianwei spit") Photopolymerization initiator D5 : 2, 4, 6-trimercaptobenzyl-diphenylphosphine oxide; ("Lucirin ΤΡ0" manufactured by BASF Corporation) <sensitizer> Sensitizer E1 : 2, 4- Diethylthioxanthone; (Kayacure DETX-S, manufactured by Nippon Kayaku Co., Ltd.) φ Sensitizer £2: 4,4'-bis(diethylamino)benzophenone; (11〇(1) EA8&amp;丫&amp; Chemical Industries, Inc. "EAB-F" <Photopolymerizable compound> Photopolymerizable compound: dipentaerythritol hexaacrylate; ("A_X M-402" manufactured by Toagosei Co., Ltd.) <Polyfunctional thiol> Polyfunctional thiol F1: Trihydroxy decyl ethane ginseng (3 - mercaptobutyrate) ("TEMB" by Showa Denko Co., Ltd.) Polyfunctional thiol F2: trimethylolpropane ginseng (3-mercaptobutyrate); (Showa 323842 211 201233734 "Electric company" "ΤΡΜΒ") Polyfunctional thiol F3: pentaerythritol lanthanum (3-mercaptopropionate); ("PEMP" manufactured by Sigma Chemical Industry Co., Ltd.) <UV absorber> UV absorber Gl: 2-[4-[2-hydroxy-3-( Dodecyl and tridecyl)oxypropyl)oxy]-2-ylphenyl]~4,6-bis(2,4-didecylphenyl)-1,3, 5-三哄;("Cumba 曰" company "TINUVIN 4〇〇") φ UV absorber G2: 2-(2H-benzotriazole_2_yl)_4,6_double (1_methyl-b stupid (ethylidene) phenol; ("CONUBA 9") manufactured by Ciba Japan Co., Ltd. <polymerization inhibitor> Polymerization inhibitor HI. N-nitrosophenylhydroxylamine aluminum salt; ("Wu Pure Chemical Industry Co., Ltd." -1301") ' Prohibition agent H2: methylhydroquinone; ("Gu" from Seiko Chemical Co., Ltd.) <Storage stabilizer> Storage stabilizer J1: 2, 6-double (1,1-dimethylethyl)-4-methyl ("BHT" manufactured by Chemical Industry Co., Ltd.) Storage stabilizer J2: Triphenylphosphine; ("Turkey Chemical Co., Ltd." "τρρ <solvent> j Organic solvent: cyclohexanone [evaluation of photosensitive coloring composition] The obtained photosensitive coloring composition has color characteristics and contrast ratio ((8), crystal precipitation on the surface of the coating film, sensitivity, linearity, pattern shape, resolution, financial imageability, chemical resistance, and stability over time) Methodological evaluation. The results are shown in the table (M0 order. The judgment in each evaluation result, 323842 212 201233734 ◎ is a very good degree, 〇 is a good degree, △ is the degree of use without obstacles 'X is used to a bad degree (Color characteristics, contrast ratio (CR) evaluation) The photosensitive coloring composition to be applied is on a glass substrate of 1 X X 〇〇 〇 〇 匪 匪 匪 匪 匪 匪 于 于 于 于 于 , , 在 在 在 在The film was applied in such a manner that the film thickness became x=0.640, y=〇.328, and dried in a hot air oven at 70° C. for 20 minutes, and then an ultrahigh pressure mercury lamp was used to carry out ultraviolet light exposure and the cumulative light amount was 150 mJ, at 23 ( After heating the TC for 1 hour, it was left to cool to obtain a red coating film. Thereafter, the brightness (Y) and the contrast ratio (CR) of the coated substrate were measured, and the chromaticity and brightness (Y) were microscopic spectrophotometers (〇1). Measurement by ympus Optics Co., Ltd. "OSP-SP200") (Evaluation of crystal precipitation on the surface of the coating film) The substrate obtained by evaluating the color characteristics and contrast ratio (CR) was heated at 260 C for 1 hour, and then left to cool. Coated substrate coating • Surface with light Under the microscope observation, the presence or absence of crystal precipitation was determined based on the following criteria. In the evaluation results, ◎ no crystal precipitation was very good, ◦ was a small amount of crystal precipitation but was good, and Δ was crystallized, but there was no problem in use. 'X is the extent to which crystal precipitation is unusable. ◎. The number of crystals is one. The number of crystals is one or more, and the number of crystals is less than ten. △ The number of crystals is 10 or more, and the number of crystals is less than one. X: The number of crystals is 100 or more (sensitivity, straight green color, pattern shape, resolution, development resistance, chemical resistance) 323842 213 201233734 evaluation) The photosensitive coloring composition obtained is 100 mm x 1 〇〇mm, 〇. 7 mm After coating on the thickness of the glass substrate, the solvent was removed by heating at 7 〇Pc for 20 minutes in a dust-free oven to obtain a coating film of about 2/m. Then, after cooling the substrate to room temperature, 'Ultra-high pressure was used. The mercury lamp is exposed to ultraviolet light through a mask of a strip pattern of 100 width (200 ym pitch) and 25/inch width (pitch 5 〇 μιη). After that, the substrate is sprayed with a sodium carbonate aqueous solution at 23 ° C. Ion exchange water Clean and air-dried, in a dust-free oven at 23〇t: heating 330 is I. Spray imaging is applied to the coating film of each photosensitive coloring composition, and the pattern can be formed without residual image development in the shortest time. This was taken as an appropriate development time. The film thickness of the coating was carried out using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.) (sensitivity evaluation)

The pattern thickness of the mask portion 7 of the filter segment formed by the above method was measured, and the exposure amount with respect to the film thickness after coating was evaluated. The smaller the minimum exposure amount, the higher the sensitivity of the photosensitive coloring composition. The rating is as follows. 〇: less than 50mJ/cm2 △: 50mJ/cm2 or more, go, go, 2 Heda 100mJ/cm2 X: 100mJ/cm2 or more (straightness evaluation) ^Offer by the above method (4) 1(10)_ The mask and pattern are observed and evaluated by an optical microscope. The evaluation of 323842 214 201233734 is as follows. 〇: good linearity △: partial linearity defect X: poor linearity (pattern shape evaluation) The pattern cross section of the 100# m mask portion of the filter segment formed by the above method was observed using an electron microscope to evaluate. The pattern profile is good for the taper. The rating is as follows. ®〇: the profile is a forward cone shape X: the profile is an inverse cone shape (resolution evaluation) The pattern of the 25/zm mask portion of the filter segment formed by the above method is observed and performed using an optical microscope Evaluation. The rating is as follows. Poor resolution means that the adjacent straight line pattern is either connected or defective. φ ◎: Good resolution and linearity 〇: The linearity is slightly inferior, but the resolution is good. △: Part of the resolution is poor X: The resolution is poor (difference evaluation) In the case of spray development The pattern thickness of the 100//m mask portion of the formed filter segment was measured twice as long as the appropriate time, and compared with the pattern film thickness formed by the appropriate development time. The rating is as follows. ◎: film thickness difference is less than 20% 323842 215 201233734 〇: film thickness difference is more than 20%, within 40% △: film thickness difference is more than 40% X: defect or peeling occurs in 2 times imaging (anti-drug evaluation) The filter fragments formed by the above method were immersed in the N-methylpyrrolidone solution for 30 minutes, washed with ion-exchanged water and air-dried, and the pattern of the 100-mask portion was observed and evaluated using an optical microscope. The rating is as follows. $ ◎: No change in appearance and color' is good 〇: Although some wrinkles occur, the color does not change as good △: Several color detachments occur X: flaking or color detachment (evaluation of the stability of the coloring composition) The obtained photosensitive coloring composition was measured for viscosity at the initial stage and room temperature after one month. The φ evaluation was performed by calculating the increase in viscosity with respect to the initial viscosity. The rating is as follows. (Change rate of viscosity over time) = I [(initial viscosity) - (time-dependent viscosity)] / (initial viscosity) 丨χ 100 «) ◎: The ratio of viscosity increase is 5% or less is good 〇: the ratio of viscosity increase is ratio 5% large and 10% or less X: viscosity increase ratio is greater than 10% 323842 216 201233734 [Table C-lο] Wrap C-10 (Evaluation 1) Brightness Y (Evaluation 2) Contrast (Evaluation 3) Crystallization (Evaluation 4 ) Weighing (Evaluation 5) Straightness (Evaluation 6) Case shape (Evaluation 7) Resolution (Evaluation 8) Resistance to development (Evaluation 9) Durability (Evaluation 10) Time stability Example 7 23.6 5300 〇〇ό 〇〇6 〇Example B 23.4 5200 〇〇〇〇η 〇Θ 〇f Example 9 22.8 5000 〇〇〇〇〇〇ο Reward Example 10 23.0 4800 〇0 〇〇〇〇Example 11 22.5 5200 &amp; 〇〇〇〇〇 Example 12 22.4 5100 〇 _ 〇〇〇〇 旄 Example 13 22.4 5300 &amp; 〇〇〇〇❺ 〇 Example 14 22.6 4700 e 〇〇〇〇〇〇 Example 15 22.1 4B00 〇〇〇〇Θ 〇d V Example 1β 22.fi 5000 &amp;〇〇〇&amp;〇&amp; . 〇V 1*7 22.2 5200 〇〇〇〇0 〇&amp; 〇会铯例18 22.1 4900 〇〇〇〇❻ 〇ΓExample 19 22.5 5400 &amp;〇〇〇〇〇&amp; 〇r vibration example 20 23.0 5300 &amp; 〇〇〇Θ 〇 &amp;&amp;&amp; 22.3 4600 &amp;&amp;&amp; ir example 22 22.4 4800 &amp;amp&amp; 〇❺ 〇 Example 23 22.S 4600 Θ 〇〇 〇&amp; 〇d 〇V Example 24 22.1 5100 ❺ amp &amp; 〇〇 Example 25 22.5 4700 ❺ 〇〇〇 〇〇〇 Example 26 22 Λ 4400 d 〇〇〇〇〇 Example 27 22.8 4600 d 〇〇〇3 〇〇〇ΓΛΜζβ 22,7 4800 Θ 〇〇❹0 〇〇❹ 〇1 “Example Ζ9 23.2 5000 &〇〇〇&amp; Poorest Example 30 22.5 5100 Ο 〇〇〇〇〇〇If Μ31 22.1 4700 &lt;a ό 〇〇β 〇〇〇霣Example 32 22.8 5100 &amp;〇〇〇&amp; 〇〇〇 施 Example 33 22.7 5300 ά 〇〇〇 &amp; 0 〇〇 Example 34 22.3 5200 &amp ; 〇〇〇 &amp; 〇〇〇 Example 35 22.2 4900 &amp; 〇' 〇&amp; 〇〇〇宝施《3β 22.1 4d00 &amp;〇〇〇&amp; 〇〇〇 施 37 37 23.0 5100 〇〇〇〇&amp; 〇〇〇 施 38 38 22.8 5000 &amp; 〇〇〇 〇〇〇〇Example 39 22.3 5000 &amp; 〇〇〇 ◎ 〇〇〇 will apply 40 22.2 4900 〇〇〇 d 〇〇〇 1 41 Example 41 22.6 5100 &amp; 〇Q 〇&amp; 9 〇〇春考Example 3 18.0 2700 X 〇5 〇△ ό ά K Reference 7 cases 4 18.4 3000 X 〇厶Δ X 〇〇〇春去例5 18.0 2500 X 〇Δ 〇XS 厶〇

As shown in Table C-10, the coloring composition for the color filter containing the pigment (Al) represented by the formula (1) and the photosensitive resin (B1) was evaluated at a high φ level in all evaluations. (Production of color filter) In the photosensitive coloring composition (RP-1), the total amount of the pigment and the pigment derivative was changed to 4.54 parts, and the green photosensitive coloring composition was CI pigment green 58/CI. Pigment Yellow 150 = 2.72 parts / 1.82 parts, blue photosensitive coloring composition is CI Pigment Blue 15 : 6 / CI Pigment Violet 23 = 3. 63 parts / 0.91 parts, the rest with pigment dispersion (P-3) In the same manner, the pigment dispersion was prepared, and the pigment dispersion of the photosensitive coloring composition (RR-1) was changed to a pigment dispersion of each color to obtain a green photosensitive coloring group for color filters. 217 323842 201233734 The light sheet is colored with a blue photosensitive coloring composition. On a glass substrate of 100 mm x 100 min, the photosensitive coloring composition (RR-1) was applied by a die coating method to a thickness of about 2 m, and the solvent was removed in a 7 〇〇c ^ baking box for 20 minutes. dry. Next, the stripe pattern is exposed by ultraviolet rays using an exposure device. The cumulative amount of exposure becomes lOOmJ/cm2. Further, the unexposed portion was removed by spray development using a developing solution of sodium carbonate aqueous solution, and then washed with ion-exchanged water, and the substrate was heated at 230 ° C for 30 minutes to form a red line having a line width of about 50 am. , wide & ® clips. Next, by the same operation 'using a green photosensitive coloring composition adjacent to the red filter segment, a green filter, a light segment is formed, and the light is colored, and the blue photosensitive coloring composition is used to form a blue filter. A color filter is obtained by obtaining a color filter having a filter of three colors on a glass substrate (&gt; when a coloring grade is used for the above color filter, a color having a wide color range can be produced. High-precision glass filter with excellent characteristics and good heat resistance. φ [Example D] In the example D, "parts" and "%" are "parts by weight" and "% by weight", respectively. The specific surface area of the pigment, the primary particle diameter of the pigment, the weight average molecular weight (Mw) of the tree t, the acid value of the resin, and the contrast ratio (CR) of the coating film are as follows. (Specific surface area of the pigment) The specific surface area of the pigment particles is a BET method by 氦1 gas adsorption, and an automatic vapor adsorption amount measuring device ("BELS0RP18" manufactured by Bell Co., Ltd.) is used in the measurement. 323842 218 201233734 (average primary particle diameter of the pigment) Pigment level The primary primary particle diameter is measured by directly measuring the size of the primary particles from an electron micrograph. Specifically, the minor axis diameter and the major axis diameter of the primary particles of each pigment are measured, and the average is regarded as the grain control of the pigment particles. 'About 100 or more pigment particles, the volume average particle size is determined as the average primary particle diameter by making the volume (reset) of each particle approximate to the obtained particle size cube. Moreover, the electron microscope uses a penetrating type. (TEm) (weight average molecular weight (Mw) of resin) GPC (manufactured by TOHHS Co., Ltd.) equipped with a TSKgel column (manufactured by Toshiba Co., Ltd.), and GPC (HLC-8120GPC, manufactured by Toshiba Co., Ltd.) was used, and polystyrene was measured using THF as a developing solvent. The weight average molecular weight (Mw) in terms of ethylene. (Acid acid value of the resin) In the resin solution 0.5 to lg, add 〇8嗣ml and water i〇mi and mix and dissolve to dissolve, 〇. lmol/L The K0H aqueous solution is used as a titration solution, and is titrated by an automatic titrator ("C0M-555"). The acid value of the resin solution is measured. Thus, the acid value of the resin solution and the solid content of the resin solution are calculated. The solid content of the resin is equivalent to the acid value. (Contrast Ratio of Coating Film) The light emitted by the liquid crystal display backlight unit is polarized by a polarizing plate, and is applied to a glass substrate by applying a dried coating film of a coloring composition. Polarizing plate. As long as the polarizing surface of the polarizing plate and the polarizing plate are parallel, the light passes through the polarizing plate, but the plate is blocked when the polarizing surface is straight. However, the polarized light is passed through the polarizing plate _== When the coating film is dried, scattering occurs due to the pigment particles. When the 323842 219 201233734 part of the polarizing surface is interlaced, the amount of light transmitted through the polarizing plate decreases when the polarizing plate is parallel, and a part of the light passes through the polarizing plate when the polarizing plate is straight. board. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates were parallel to the luminance at the time of straight running (contrast ratio) was calculated. (Brightness when the contrast ratio is parallel) / (Brightness when going straight) At the same time, a color luminance meter (Το%. "BM-5A" manufactured by the company) is used as the meter, and a polarizing plate is used as the polarizing plate. Electrician company

"Foot-G122_N". At the same time, in order to block more light during the measurement, a black mask with a 1 cm square hole is placed on the test portion before the embodiment, and the adhesive resin (8) used in the examples and the reference examples is described. A method for producing a pigment (A1), a fine pigment, and a pigment dispersion represented by the formula (1). &lt;Method for Producing Binder Resin (B) Solution> [Resin Solution (B1-1)] (Stage 1: Polymerization of Resin Main Chain) The 4-neck flask in the roasting type has a thermometer, a cooling tube, and a gas Add propylene glycol monomethyl acetate to the reaction vessel of the introduction tube and the stirring device. PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG PG Part, the second pentyl methacrylic acid: 41.0, and the mixture of the azobisiso-T nitrile required for the catalyst combination in the previous stage, the sputum mixture, into the dodge reaction. (Stage 2: Polymerization of epoxy groups) ' Then the air is replaced by burning (4), and the (4) acid is used for 17 parts and 323842 220 201233734. In this stage, the polymerization of the precursor is required as a catalyst. 3 parts, and hydrogen hydrazine. 3 parts, when the shoe is reacted =, the weight of the square molecular weight is about 12 coffee (measured by GPC), and the (tetra) acid fine methacrylic acid is obtained. Shrinking water (four) Cheng j oxy end of the (10) knot, so the lion construction towel does not produce line base. Fear (stage 3: polymerization of hydroxyl groups) a v, adding tetrahydrophthalic anhydride 3 〇. 4 parts and at this stage

The required three of the three as the catalyst are 5, and should be 4 hours. The addition of 匕 之 2 2 : : : : : : : : : : : : 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 Another ~ (stage 4: adjustment of non-volatile components) 40% was obtained by adding a propylene glycol monomethyl group to make a nonvolatile component into a resin solution (B1-1). The weight ratio of the constituent units in the resin solution (B1-1) is 2% by weight of the tetrahydrofurfuric acid liver of the unit (D-bl), and is a constituent unit: the present ethylene is U. 6 wt% as a constituent unit. (D_b3) 2) acrylic acid vinegar · 29.3 wt%, as the other constituent unit, the succinic acid (4) and the glycidyl (tetra) terminal _ knot 37.4% by weight. [Resin solution (Β1-2)] The dicyclopentanyl methyl acrylate of the resin solution (ΒΗ) is formed into a mixture of the following: the rest of the system and the resin solution (ΒΗ The same method is used for the synthesis reaction, and the result is _ lipid return. 2). 323842 221 201233734 [Resin solution (Bl-3)] The dicyclopentenyl methacrylate of the resin solution (B1-1) is formed into a dicyclopentenyloxyethyl methacrylate, and the rest is resin. The synthesis reaction is carried out in the same manner as the solution (B1 -1) to obtain a resin solution (b 1 to 3 ) [resin solution (B1-4)] provided with a thermometer, a cooling tube, a nitrogen introduction tube, a drip tube, and a search device. 370 parts of PGMEA was added to the separable 4-necked flask, and the temperature was raised to 8 (rc. After the nitrogen substitution in the flask, the isopropyl phenylphenol oxirane modified acrylate was added dropwise by dropping the tube for 2 hours. (Ar东亚nix Ml 10 manufactured by Toagosei Co., Ltd.) 18 parts, 1 part by weight of benzyl methacrylate, 18.2 parts of glycidyl methacrylate, 25 parts of decyl methacrylate, and 2, 2, _ double pairs Isochao 2.0 parts of the mixture. After the instillation, 'further, after reacting for 3 hours at 1 °C, 'addition of 1.0 part of azobisisobutyronitrile to 5 parts of cyclohexanone' and then 10 0 C The reaction was continued for 1 hour. Then, the container was replaced with air, 9.3 parts of acrylic acid (epoxy equivalent) and dimethylamine. Phenolphthalein 5 φ parts and hydrogen hydrazine. 1 part was placed in the above-mentioned container, and 12 (TC was continuously reacted for 6 hours, when the solid content of the acid was 0.5 part), the reaction was completed, and a solution of the two dilute acid resins was obtained. Further, 5份。 The equivalent of the tetrahydrofuran anhydride 丨 9.5 parts (the equivalent of the formed base), diethylamine 0.5 parts, to 12 〇. (: continuous reaction &amp; 5 hours, to obtain a solution of acrylic resin. After cooling to room temperature, the resin solution was used as a sample, and the non-volatile age was measured at 18 (rc heating and drying for 20 minutes), PGMEA was added to the previously synthesized resin solution to make the nonvolatile content 2% by weight, and acrylic acid was prepared. Resin solution (BH). The weight average molecular weight (Mw) is an ankle. 323842 222 201233734 [Resin solution (B1-5 to 15) and (B2-1 to 4)] In the same manner as the resin solution (B1-1) The resin solution is prepared to (B1-15) and (B2-1) to (B2 to 5). That is, in the method for producing the resin solution (B1-1), the constituent unit (D-bl) is used as D-b3) and other constituent units of the precursor are replaced by Table D-丨. Resins not present in the table GMA-AA or GMA-MAA In the case of solution, all of the ruthenium precursors are mixed, and only stage 1 and stage 4 of the production are carried out. In the table, GMA-AA or GMA-MAA is present, and when τηΡΑ is further present, the GMA and the constituent unit are first mixed (D- In the b2), (D-b3) and other constituent units, the precursor of GMA-AA or GMA-MAA is removed to carry out the stage 1 of the production, and then the epoxy equivalent of AA or MM of GMA is added as a precursor to manufacture. In stage 2, phase 3 and stage 4 of manufacturing are carried out by adding THPA as a precursor. In the table, GMA-AA or GMA-MAA is present. When THPA is not present, the precursors of GMA-AA or GMA-MAA are first mixed with GMA and constituent units (D-bl) to (D-b3) and other constituent units. The stage of manufacture φ 1 'and then the addition of AA or MAA of the epoxy equivalent of GMA as a precursor to the stage 2 of the manufacturing process is carried out. The number of catalysts required for each stage is mixed according to the proportion of the total number of parts of the precursor before mixing in each stage. The composition and weight ratio of the obtained resin solutions (B1-1 to 15) and resin solutions (B2-1 to 4) are shown in Table D-1. The brackets indicate the constituent unit weight ratio (% by weight) in the resin solid portion. 323842 223 201233734 [Table D-l]

蠡D-1 Resin solution name «1 into unit (bl) 铕 筚 constituting 筚 ( (b2) 麻 物 物 物 物 物 物 物 物 物 物 物 物 物 物 其他 其他 其他 其他 其他 其他 其他 其他 其他 其他 其他 其他Molecular weight dissolved non-volatile content ratio 1-1 THPA (21.7 霣皇St (11.6SJ|9«) DCPMA (29.3 reset Η) GMA-AA (37.4ttftM) 100 灵董% 12000 PGMAC 40 Xia Η Θ 1 -2 THPA(21.7l*H) St(11.6 霣灵%&gt; 7-base propionate dicyclodecene" (29.3 heavy Dong GMA-AA (37.4^ftH> 1001 Η 12500 PGMAC 40 灵·% B1- 3 THPA (21.7MH) Stdldlft%) Hydrazinylbicyclononyloxy &曲&lt;29.3 偷噩(6) GMA-AA&lt;37.4 Poor 10〇1%% 12800 PGMAC 40 霣ft% B1-4 MAA( 25 weight ·%) BzMAOOSftM) DCPMA (19.5 ft%) GMA-AA (27.5 reset 100 wear expensive % 19000 PGMAC 20 reset % B1-6 THPACZfiM%) St (4 weight 1%) DCPMA (25 麓 know GMA-AA (43 ft%) 100 reset % 8000 PGMAC 40 妁 妁 B1-6 1&gt;^ six (22 resets st (10l set DCPMA (24ftftM) GMA-AA (44 reset %) 100 窜ΜΗ 9000 环己明20重霣% B1-7 MAA(16U%) BzMA(09% suspected) OCPMA(15 籯置- lOO Sft% 16000 PGMAC 40 创Β1-Θ MAA(13 霣丽%) BzMA(49ftK%) OCPMAdSflft%) OMA-MAA(23M%) lOOftM% 27000 PGMAC 40 weight·% B1-9 MAA(16Mft%) BzMA(S7 Weight ft%) DCPMA (丨3wt%&gt; QMA-MAACl4ftft%) 100 Party%% 9000 PGMAC 40 Li 11% B1-10 MAA(,3 tributary%} βιΜΑ(53 weight most) DCPMA&lt;13XJ|% ) GMA-MAA (21% of the weight> 100% of the farmers 27000 PGMAC 40鬣% B1-11 MAA (57lfl;%) St (1〇S amount%) DCPMAU3 Zhenli GMA-MAA (13 weight · βΜΑ ( 7 重·Η) 100% of wear 1S500 PGMAC 40 霣B1-12 THPA (11.5 snow %) BzMA (11.5l ftM) OCPMA (S6lM%) GMA-AA (21% by weight) ιοοΧΜ% 14000 PGMAC 40%·% B1-13 MAA (42flft%) ΒζΜΑ&lt;43 weight most %&gt;DCPMMl5SJt%&gt; - UW weight 96 15000 ring already clear 40 ft% B1-14 MAA (44 % quantity%> SU7M%) OCPMA (49Sft% ) - 100Μ% 21000 PGMAC 40 重丽铋B1-15 MAA(1)Exposure%&gt; BzMA(41 重ftH> 〇CPMA(45 党腾GMA-MAA(Resuspension 39〇1001196 100500 PGMAC 40 霣·% Θ2-1 THPA (30.7ll%) St (16.4 reset %) 垂 GMA-AA (52.9 % %) 100% 1 11000 PGMAC 40羹Μ B2—2 THPA (24.6 霣·axis) - DCPMA (33.1 霣鸶%) ΟΜΑ-ΑΑ (42·3 100100 heavy egg% 9500 PGMAC 40 weight 1% BZ-3 - st (Me repeat %) DCPMA07.4S GMA-AAC47.8 weight ft%) 100 wear most % 12000 PGMAC 40 Ling B2-4 MAA (32%) BzMA "Large weight ft%" - • 100% by weight 18000 PGMAC 40% The abbreviations of the precursors and constituent units of the constituent units in Table D-1. MAA: methacrylic acid THPA: tetrahydrophthalic anhydride (4-cyclohexene-1,2-dicarboxylic anhydride)

BzMA ·. phenyl decyl acrylate St: styrene 224 323842 201233734 M110 : p-cumylphenol oxirane modified acrylate DCPMA: dicyclopentenyl acrylate GMA: glycidyl methacrylate S GMA-AA: Addition reaction in the constituent unit GMA Acrylic bond and bond GMA-MAA: Addition reaction methacrylic acid in the constituent unit GMA and bond BMA: n-butyl decyl acrylate [resin solution (B2-5 The methacrylate dimethyl methacrylate was added dropwise to the reaction vessel while immersing 370 parts of cyclohexanone in the reaction vessel while injecting nitrogen gas into the vessel to a temperature of 80 ° C. 0份的混合物进行进行进行。 0. 0 parts, n-butyl methacrylate 55.0 parts, 2-hydroxyethyl methacrylate 15.0 parts, 2, 2'- io II bisisobutyronitrile 4. 0 parts of the mixture for polymerization reaction. After the completion of the dropwise addition, the reaction was further carried out at 80 ° C for 3 hours, and then 1.0 part of azobisisobutyronitrile was dissolved in 50 parts of cyclohexanone, and further, the reaction was continued at 80 ° C for 1 hour to obtain propylene. Acid resin solution. After φ was cooled to room temperature, about 2 g of the acrylic resin solution was used as a sample, and dried at 180 ° C for 20 minutes, and the nonvolatile matter was measured, and cyclohexanone was added to the previously synthesized acrylic resin solution to make the nonvolatile matter 20% by weight, and the resin solution (B2-5) was prepared. The weight average molecular weight (Mw) was 40,000. &lt;Production Method of Pigment (A1) Represented by Formula (1)&gt; [Bromide Diketopyrrolopyrrole Pigment (A1-1)] In a stainless steel reaction vessel equipped with a reflux tube, under a nitrogen atmosphere, 200 parts of the third pentanol dehydrated by the molecular sieve and 140 parts of the third pentyloxy 323842 225 201233734 sodium were added, and the mixture was heated to 100 ° C while stirring to prepare an alkoxide solution. Further, 88 parts of diisopropyl succinate and 156.6 parts of 4-bromobenzonitrile were placed in a glass flask, and the mixture was heated to 90 ° C while stirring to dissolve, and a solution of these mixtures was prepared. The heated solution of the mixture was vigorously stirred at a constant rate for 2 hours while vigorously stirring in the above alkoxide solution heated to 100 °C. After the completion of the dropwise addition, the mixture was stirred at 90 ° C for 2 hours to obtain an alkali metal salt of a compound having a diketone ratio of p and a specific ratio of σ. Further, in a reaction vessel with a glass lining, sterol ® 600 parts, water 605 parts, and acetic acid 340 parts were added, and the mixture was cooled to -10 °C. The cooled mixture was rotated at a speed of 4000 rpm using a high-speed stirring disperser, and a small amount of diketone 吼σ was added to the mixture before the cooling to 75 ° C. Check the metal salt solution. In this case, the temperature of the mixture of decyl alcohol, acetic acid, and water is maintained at a temperature of -5 ° C or lower, and the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C is adjusted while cooling. The speed is about 120 points and less. After the gold deposit was added, red crystals were precipitated to form a red suspension. Then, the obtained red suspension was washed at 5 ° C in excess of the apparatus, and then filtered to obtain a red paste. The paste was cooled and redispersed in 3500 parts of methanol at 0 ° C to form a suspension having a decyl alcohol concentration of about 90%, and stirred at 5 ° C for 3 hours to granulate and wash the particles accompanying the crystal transfer. . Then, the water paste of the obtained diketopyrrolopyrrole compound was dried at 80 ° C for 24 hours by an ultrafilter, and 150.8 parts of the pigment (A1) represented by the formula (1) was obtained by pulverization. Brominated diketopyrrolopyrrole pigment. 323842 226 201233734 The obtained brominated diketopyrrolopyrrole pigment 100. 0 parts, 1000 parts of sodium chloride and 120 parts of diethylene glycol were poured into a stainless steel 1 gallon kneader (manufactured by Inoue Co., Ltd.) to Mix at 80 ° C for 8 hours. Next, the kneaded mixture was put into warm water and heated to about 80 ° C - while stirring for 1 hour to form a paste, which was filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. By day and night, 95.6 parts of the brominated diketopyrrolopyrrole pigment (Ab) represented by the formula (1) was obtained by pulverization. The average primary particle diameter was 38 mm and the specific surface area was 80 m 2 /g. <Manufacturing method of pigment dispersion 〉> [Pigment dispersion (P-1)] A mixture of the following composition was stirred and mixed uniformly, and then an Eiger grinding machine (manufactured by Eiger Japan Co., Ltd.) was used. "Minimodel M-250 MKII" was dispersed for 5 hours, and then filtered through a 5/zm filtration membrane to obtain a pigment dispersion (P-1). Brominated diketopyrrolopyrrole pigment (A1-1) 8. 78 parts φ Acid resin type pigment dispersant 1.74 parts (BYK-111, manufactured by BYK Chemie Japan Co., Ltd.) Pigment derivative 1 2. 05 parts 323842 227 201233734 Derivative 1

Resin solution (B2-5) cyclohexanone

5. 83 parts 81.60 parts [Pigment dispersion (P-2)] In addition to changing the brominated diketopyrrolopyrrole pigment (A1-1) to chlorinated diketopyrrolopyrrole pigment (CI Pigment Red 254; steam A pigment dispersion (P-2) was obtained in the same manner as the pigment dispersion (pi) except for "Irgaphorred B-CF" manufactured by Babel Corporation. [Pigment Dispersion (P-3)] The mixture of the following composition was stirred and mixed uniformly, and then dispersed using an Eiger mill ("Minimodel M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using a oxidized beads of a diameter of 1 min. After 5 hours, it was filtered through a 5/zm filtration membrane to obtain a pigment dispersion (p_3). Brominated di-jj-based pyrrolopyrrole pigment (A1_i) 6. 82 parts of anthraquinone pigment (c. I. Pigment Red 177) 1·08 parts ("Chromophtal red A2B" manufactured by KBA Japan) Compound pigment (CI Pigment Yellow 150) 0. 88 parts ("E4GN" manufactured by Lanxcess) 323842 228 201233734 Acid resin type pigment dispersant 1. 74 parts (Solsperse 21000, manufactured by Lubrizol, Japan) Pigment derivative 1 2. 05 Derivative 1

Resin solution (B2-5) 5. 83 parts of cyclohexanone 81. 60 parts [Pigment dispersion (P-4 to 10)] except for the pigments, pigment derivatives, and resin type pigments shown in Table D-2 A pigment dispersion (P-4 to 11) was obtained in the same manner as the pigment dispersion φ (P-3) except for the type of the dispersant and the blending amount. [Table D-2] Table D-2 Pigment Dispersion Pigment 1 Pigment 2 Pigment 3 Pigment Derivative Partition Part P-3 A1 — 1 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P-4 PR254 6.82 PR177 1.08 PY150 0.88 Derivative 1 2.05 P-5 A1 ~1 6.82 P071 0.65 PY150 0.88 Derivative 1 2.05 P-6 A1-1 6.82 PR242 0.60 PY150 0.88 Derivative 1 2.05 P-7 A1 — 1 6.82 PR179 0.50 PY150 0.88 Derivative 2 2.05 P —8 A1-1 6.82 PR122 0,55 PY150 0.86 Derivative 3 2.05 P-9 A1-1 6.82 PR177 1.08 PY180 0.50 Derivative 4 2.05 P-10 A1 —1 6.B2 PR177 1.08 PY138 0.55 Derivative 1 2.05 229 323842 201233734 The abbreviation in Table D-2 is described below. &lt;Pigment&gt; PR 254: Diketopyrrolopyrrole pigment CI Pigment Red 254; "Irgaphor redB-CF" manufactured by Ciba Japan Co., Ltd. P071: Diketopyrrolopyrrole pigment CI Pigment Red 71; Ciba Japan "Irgazin DPP orange398" manufactured by the company PR242: azo pigment CI Pigment Red 242; "Novoperm" manufactured by Clariant Co., Ltd. 0 PR 179: lanthanide pigment CI Pigment Red 179; Dainippon Ink Chemical Industry Co., Ltd. "Fastogen Super Maroon PSK" PR 122: 丫 丫 ketone pigment CI Pigment Red 12; "HOSTPERM" manufactured by Clariant PY180: benzimidazolone pigment CI Pigment Yellow 180; "PV First Yellow HG" manufactured by Clariant Co., Ltd. PY138: Quinoline pigment CI Pigment Yellow 180; φ "Paliotol Yellow K0960-HD" made by BASF &lt;Pigment Derivatives&gt; 323842 230 201233734 Derivative 2

φ derivative 4 [Example 1] (Red coloring composition (DR-1)) A mixture of the following composition was mixed and uniformly mixed, and then filtered through a membrane of 5 #m 323842 231 201233734 to obtain a red colored composition. (DIM). Red pigment dispersion (P_R1) Resin solution (B1-1) 40, 5 parts of cyclohexanthene with 8·6 parts [Examples 2 to 6 and reference examples ^ 50. 9 parts (red coloring composition (J) R- 2 to γ)) except for the resin solution (B i), the remaining lines were mixed with the red coloring group composition (DR-2 to 7). [Reference Example 2]

The resin solution shown in Table D-2 was colored red in the same manner as the product (DR-1) (red coloring composition (DR-8)) except that the red pigment dispersion (P_R1) was changed to red pigment dispersion. The red coloring composition (DR-8) is the same as the "other coloring composition (10) - 丨) other than the body (P-R2). [Evaluation of Red Colored Composition] The color characteristics, the contrast ratio (CR) of the obtained red colored composition, and the crystallization of the surface of the coating film were evaluated by the following methods. The results are shown in Table D-3. (Color property, contrast ratio (CR) evaluation) The red coloring composition was applied to a glass substrate of 1 mm×10×10 mm thick and 0.7 mm thick, and the film thickness was made to be χ=〇644 in the c light source. Applying y = 0.340 (within ± 0.001), and drying at 7 (TC hot air oven for 20 minutes) and further heating at 230 ° C for 60 minutes to obtain a red coating film. Thereafter, the obtained coated substrate was measured. Brightness (Y) and contrast ratio (CR) 323842 232 201233734 Further, chromaticity and luminance (Y) were measured by a microspectrophotometer ("0SP-SP200" manufactured by Olympus Optics Co., Ltd.). (Crystal precipitation on the surface of the coating film) Evaluation) The substrate obtained by evaluation of color characteristics and contrast ratio (CR) was further subjected to heat treatment at 240 ° C for 60 minutes twice. The surface of the coating film of the coated substrate after heat treatment was observed by an optical microscope, according to the following. The evaluation was carried out to determine whether or not crystals were precipitated. In the evaluation results, ◎ and lanthanide crystals were not precipitated well, △ was crystallized, but there was no problem in use, and X-based crystallization was equivalent to an unusable state. ◎ : 230 °C heat treatment 6 After 0 minutes, further heat treatment at 240 ° C for 60 minutes, and further heat treatment at 240 ° C for 60 minutes, no crystal precipitation 〇: heat treatment at 230 ° C for 60 minutes, and further heat treatment at 240 ° C for 60 minutes No crystal precipitation (the second 240 ° C heat treatment for 60 minutes, crystal precipitation) △: 23 (TC heating treatment for 60 minutes without crystal precipitation, but further 240 ° C plus φ heat treatment for 60 minutes, crystal precipitation X: 230 ° C Crystallization occurred after 60 minutes of heat treatment [Table D-3] Table D-3

Ττ_color coloring composition red pigment dispersion resin solution brightness (Υ) CR crystallization precipitation Example 1 DR-1 Ρ-1 Β1-1 24.56 10330 ◎ Example 2 DR-2 Ρ-1 Β1-2 24.12 11000 ◎ Example 3 DR-3 Ρ-1 Β1-3 23.01 10550 ◎ Example 4 DR-4 Ρ-1 Β1 -4 23.78 10760 ◎ Example 5 DR-5 Ρ-1 Β1-7 25.61 10620 ◎ Example 6 DR -6 Ρ—1 Β1-11 23.88 12020 ◎ Reference example 1 DR-7 Ρ—1 Β2-1 20.02 5390 X Reference example 2 DR-8 Ρ—2 Β1—1 20.96 5690 X 323842 233 201233734 Contains formula (1) Any of the coloring compositions for the color filter (A1) and the resin (D-B1) having the constituent units (D-bl) to (D-b3) are high in brightness and high in contrast ratio, even if Good results were obtained without precipitation of crystals of the diketopyrrolopyrrole pigment in the heating step. [Examples 7 to 31, Reference Examples 3 to 9] [Photosensitive coloring composition (PR-1 to 32)) The compositions shown in Tables D-4 to 10 were mixed and stirred in a blending amount to obtain The filter membrane of //m was filtered to obtain a photosensitive coloring composition (PR-1 to 32). [Table D-4] «0-4 Example 7 Implementation W 8 Example 9 Example 贲 Example 11 RR-1 RR-2 RR-3 RR-4 RR-5 杈》名丨重林» Name; Weight % «m name: 嚣营% tree η name ft% material name heavy weight % pigment dispersion P-3 ! 40.5 P-3 · 40.5 P-3 ! 40.5 P-3 40.5 P-3 40.5 blush solution B1- 1 : 24.8 B1—2 J 24.8 B1 -3 ; 24.8 B1-4 24.8 B1-5 24.8 Photopolymerization start #I(D&gt; D6 : 0.77 D6 ! 0.77 D6 ! 0.77 06 0.77 D6 0.77 Sensitizing shot (ε > : : First polymerizable compound (C) C1 : 5.25 C1 : S.25 C1 : 5.25 C1 5.25 C1 S.25 Multi-manganese sulfonium (F) · ί • 1 UV absorption X (G) &lt; 1 • Storage a stable剤(j> • 1 Solvent PGMAC · 28.88 PGMAC; 28.68 PGMAC i 28.68 PGMAC 28.68 PGMAC 28.68 Total: 100 100: 100 100: 100 100 100 100 100 [Table D-5] &gt;0-5 Example 12 f Example 13 J*Example 14 Lean application 15 r Example 16 RR-6 RR-7 RR-8 RR-9 RR-10 Material Name Quantity % Material Name Setting H Material Name MM2L ggA__ mm% Pigment DispersionΡ -3 40.5 P-3 40.5 P-3 40.5 P-3 40.S P-3 40.S Resin solution Β1- 6 24.B B1-7 B Bu 10 Θ.6 16.2 B1-8 24.8 B1-9 24.8 B1-10 24.8 Photopolymerization initiator (D) DA 0.77 Οβ 0.77 D6 0.77 D6 0.77 D6 0.77 1 polymerizable compound ( C) 1 C1______ 5.25 Cl 5.25 Cl 5^5 C1 5.25 C1 5.25 Polyfunctional ( (F> UV Absorber (G&gt; Storage Stabilization ω) Dissolved $ PGMAC 28.ββ PGMAC 28.68 PGMAC 28.68 PGMAC 28.68 PGMAC 28.68 Total i 100 1 i 1001 1 1 1001 II 1001 ί 100 234 323842 201233734 [Table D-6] Table D-β Example 17 Example 18 Example 19 Example 20 1 ★ Example 21 ~ RR-11 RR-12 RR— 13 RR-14 IrR~15 Material Name tn isizUimmn xmiinimmn 1 颜料 Pigment dispersion P-3 : 40.5 P-3 : 40.5 P-3 : 40.5 P-3 : 40.5 P-3 : 40.5 * B1-9 ; β. 4 B1-11 : 8.4 1 Rouge solution BT-11; 24.8 B1-12 : 24.8 B1-11 : 8.4 B1-12 : 8.4 Bl-15 : 24.8 • • Θ1-13 : 8 Bl-14 : β photopolymerization Start (D&gt; D6 • 0.77 D8 1 0.77 Οβ i 0.77 D6 ! 0.77 D6 • 0.77 Jfifl-KE) 1 : 1 1 : 1 1 : 1 El : 0.3 Compound (C) IC1 ί 5.251 IC1 Ϊ 5.25i Cl : 5.25 lei ϊ 5^51 Cl ί 5.25 Multi-manganese thiol (F*) : 1 » * 丨FI ! 1 UV absorption 剤 (G > 1 » • j Q1 ί 0.22 Storage Ding Xie (J) 1 • J1 ! 0.25 Dissolved IPGMAC : 28.6BI IPGMAC : 28.661 PGMAC : 28.68 IPGMAC : 28.68! PGMAC ί 27.91 Total 1 ί 1001 I ί 1001 ? 100 1 ί 1001 1 i 1001 [Table D -7] *D-7 霄 Example 22 贲 Example 23 Reward Example 24 赀 Example 5 Example 2 β RR-16 RR —17 RR-18 RR -19 RR-20 lliUWM ; Reset % Material Name i % by weight Sealing soap z% by weight Proxies dispersion P-5 ί 35.6 P-6 ; 29.6 P-7 36.4 P-8 ; 3β.4 P-9 3β.β Rouge solution B1-1 ! is.e B1 -1 ! 22.4 B1-1 18.9 B1-1 ! 36 B1-1 27.2 First polymerization start system (D) D1 : 0.75 D2 : 0.25 D3 0.63 D4 ! 1.22 DS 0.82 礒a agent (ε) Et ; 0.25 E2 : 0 33 1 ί 1 1 : 1 Photopolymerizable compound (C) Cl j 4.4β C1 • 2.89 C1 5.53 IC1 5.551 Cl 4.35 1 Multi-dense sulphur fermentation (F) ! 1 1 : 1 F1 0.63 F2______ 0.33 F3 0.51 UV-induced System (〇&gt; IG1: 0.25! G2 0.25 Storage stability (j > I ! I I ! I dissolution 1 IPGMAC ; 39.341 IPGMAC : 44.281 IPGMAC ; 37.661 IPGMAC : 20.5! PGMAC 28.32 Total 1 i 1001 I ! 1001 I ! 1001 1 ! 1001 1 i 1001

[Table D-8]

ap-B

T Example 27 Example 28 I Example 29 I Example 30 Example 31 RR-21 RR-22 RR-23 RR-24 RR a 25 Material name j Reset consumption "Name weight % + weight %枓Dispersion « P-10 : 33.6 P-3 33.8 P-3 33.9 P-9 : 43.5 P-3 : 35.B blush solution B1-1 : 26.7 B1-1 33.1 Β 1-Ί 27.6 B1-1 18.3 B1- 1 : 20.8 D6 ! 0.77 06 0.77 D6 0.77 D6 ! 0.77 D6 : 0.77 Sensitizer (E&gt; I : II : I 丨: 1 ί : I E1 ! 0.55 Electropolymerizable compound (C) IC1 i 3.681 IC1 · 4.981 IC1 i 4.681 IC1 ! 4.02I C1 :4.62 Multi-sense Moisture Selection (F) : 1 I : I 1 • _ 1 F1 : Ο.ββ UV Absorber (G) IQ1 :0.271 IG2 : 0.291 , \ 1 (J&gt; I : II : I J1 ; 0.33 J2 ; 0.56 I 丨 Cyclohexanone: 34.7β! IPGMAC : 27.061 PGMAC ! 32.72 PGMAC : 32.85 Cyclohexanone: 38.BI Total 丨: 1001 I : 1001 I : 1001 1 : 1001 I : 100! [Table D-9] Table D-9 I Reference Example 3 [RR-26 I Reference Example 4 IrR-27^ I Reference Example 5 I Reference Example IRR — 2 I McGrade IRR-5 30 Pigment Dispersion\asmm ί 40.5 P-3 ! 40.5 P-4 38.7 P-4 ! Γ 37. 8 Rouge solution B2-1 24.8 Β2-2 24.8 B2-3 : 24.8 B2-1 33 B2-2 27.9 Photopolymerization start 剤 (D) D6 0.77 D6 : 0.77 D6 j 0.77 D6 0.77 D6 · 0.77 Sensitized 剌 ( E) I 1 1 El 0.26 fc polymerizable compound (C) C1 5.25 C1 5.25 C1 : 5.25 Cl 4.25 Cl 4.66 ί 官 琉 ( ( ( 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 紫外 ( ( ( J1 0.25 Solvent PGMAC 28.68 PGMAC : 28.68 Cyclohexanone I : 28.68 PGMAC 23.02 PGMAC 28.62 Total 100 100 100 100 100 323842 235 201233734 [Table D_ 10 ] Table D-10 Reference Example 8 Reference Example 9 RR-31 RR—32 Material Name Reset % Material Name Weight % Pigment Dispersion ρ - 4 38.9 Ρ - 4 34.7 S Month Solvent Β 2 - 3 30.1 Day 1 - 1 20.6 Photopolymerization Starter (D) D7 0.77 D6 0.77 Sensitization ϋΕ) Photopolymerization Compound (C) C1 3.36 Polyfunctional thiol (F) UV absorber (G) G1 0.46 Storage stabilizer (J) J2 0.33 Solvent PGMAC 26.08 Cyclohexanone 43.93 Total - 100 100 Tables D-4 to 10 Expressed below. &lt;Photopolymerization initiator 〇))&gt; Photopolymerization initiator D1.· 2-mercapto-1-[4-(indolylthio)phenyl]-2-morpholinylpropan-1-one ("Irgacure 907" manufactured by Ciba Japan Co., Ltd.) Photopolymerization initiator D2: 2-(dimethylamino)-2-[(4-methylphenyl)fluorenyl]-l-[4-(4 -morpholinyl)phenyl]-1-butanone ("Irgacure 379" manufactured by Ciba Japan Co., Ltd.) Photopolymerization initiator D3: 2, 4, 6-trimercaptophenyl-diphenyl-oxidation Phosphorus ("Lucilin ΤΡ0", manufactured by BASF Corporation) Photopolymerization initiator 04: 2,2'-bis(〇-chlorophenyl)-4,5,4',5'-tetraphenyl-1,2' - Biimidazole ("Biimidazole" manufactured by Heijin Chemical Co., Ltd.) Photopolymerization initiator D5: p-didecylaminoethyl benzene ("DMA" manufactured by Daiki F ine Co., Ltd.) Photopolymerization initiator D6: ethane-1 -ketone, l-[9-ethyl-6-(2-methylbenzone 323842 236 201233734 brewing base)-9Η-α卡β坐-3-yl], 1-(o-ethylidene) (steam) "Irgacure OXE02" manufactured by Baline Co., Ltd. &lt;sensitizer&gt; Sensitizer E1: 2, 4-diethylthioxanthone (Kayacure DETX-S, manufactured by Nippon Kayaku Co., Ltd.) Sensitizer E2: 4 , 4'-bis(diethylamino)dibenzophenone (H "EAB-F" manufactured by Odogaya Chemical Co., Ltd. &lt;Photopolymerizable compound&gt; ® Photopolymerizable compound Cl: Dipentaerythritol hexaacrylate ("Aronix M-402" manufactured by Toagosei Co., Ltd.) &lt;Multifunctional thiol&gt; Polyfunctional thiol F1: trihydroxy decyl ethane ginate (3-mercaptobutyrate); ("TEMB" manufactured by Showa Denko Co., Ltd.) Polyfunctional thiol F2: trimethyl methacrylate (3-Wikidin) Acid ester); (TPMB) manufactured by Showa Denko Co., Ltd. φ Polyfunctional thiol F3: pentaerythritol lanthanum (3-mercaptopropionate); ("PEMP" manufactured by Sigma Chemical Industry Co., Ltd.) &lt;Ultraviolet absorbing agent&gt; Ultraviolet absorption Agent G1: 2-[4-[(2-hydroxy-3-(dodecyl and tridecyl)oxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis (2) , 4-dimethylphenyl)-1,3, 5-triphthol ("TINUVIN 400" manufactured by Ciba Japan) UV absorber G2: 2-(2H-benzotriazol-2-yl)-4 , 6-bis(1-mercapto-1-phenylethyl)phenol; (rTINUVIN 900, manufactured by Ciba Japan) 323842 237 201233734 &lt;Storage stabilizer&gt; Storage stabilizer Jl: 2, 6-double ( 1, di-diylethyl)_4_methylphenol (this "BHT" manufactured by Chemical Industry Co., Ltd. Storage stabilizer J2: Triphenylphosphine ("τρρ", manufactured by Kitagawa Chemical Co., Ltd.) &lt;Solvent&gt; PGMAC: Propylene glycol monodecyl ether acetate vinegar [Evaluation of photosensitive coloring composition] With respect to the obtained photosensitive colored composition (pR_1 to 32), color characteristics, contrast ratio (CR), crystal precipitation on the surface of the coating film, sensitivity, linearity, pattern shape, resolution, and image formation were evaluated by the following methods. Sex, chemical resistance, stability over time. The results are shown in Table D-ii. In the judgment of each evaluation result, ◎ is very good, the degree of lanthanism is good, △ is not inhibited from use, and X is not used to the extent. (Color property, contrast ratio (CR) evaluation) The obtained red coloring composition was applied onto a glass substrate of 100 mm×100 mm and 0.7 mm thick, and post-treated in a c light source so that the film thickness became χ=0·640. And y = 0.28, and dried in a 7 (rc hot air oven for 20 minutes, using an ultra-high pressure mercury lamp, ultraviolet light exposure at a cumulative light amount of 150 mJ, and then left at 23 (TC heating for 1 hour) to obtain a red color. After the coating film was measured, the brightness (γ) and the contrast ratio (CR) of the obtained coated substrate were measured. The 'chromaticity and brightness (Y) were measured by a microspectrophotometer ("OSP-" manufactured by 〇lympus Optics Co., Ltd. SP200") 323842 238 201233734 (Evaluation of crystal precipitation on the surface of the coating film) The substrate obtained by evaluation of the color characteristics and contrast ratio (CR) was further heated at 260 ° C, and then left to cool. The surface of the coating film of the coated substrate after the heat treatment was observed under the microscope. The presence or absence of crystal precipitation was evaluated according to the following criteria. In the evaluation results, no crystals were precipitated very well, and a small amount of crystals were precipitated in the lanthanum, but the degree of goodness was good. Have a knot The degree of crystallization is 0, and the number of crystals is 0 or less, and the number of crystals is less than 10, and the number of crystals is 10 or more. Less than 100 X: The number of crystals is 100 or more (sensitivity, linearity, pattern shape, resolution, development resistance, and chemical resistance). The obtained photosensitive coloring composition is applied to 1QQmm. After springing on a 7iim thick glass substrate, the solvent was removed by heating at 7 Torr for 2 Torr in a dust-free oven to obtain a coating film of about 2 # m. Then, after cooling the substrate to room temperature, 'use The ultra-high pressure mercury lamp is exposed to ultraviolet rays through a strip of 1 〇〇/zm width (between 2〇7〇#m) and 25/zm (pitch 50//m). Thereafter, the substrate is used. After spraying with a sodium carbonate aqueous solution at 23 ° C, it was washed with ion-exchanged water and air-dried, and heated in a dust-free oven at 23 ° C for eight minutes. The spray imaging system was applied to each photosensitive coloring composition. The film, without image retention, is carried out in the shortest time that can be patterned, as a suitable time: '323842 239 201233734 Film thickness of the coating film was carried out using Dektak3_ (manufactured by Nippon Vacuum Technology Co., Ltd. (sensitivity evaluation). The io&quot;m mask of the filter and light fragments formed by the two methods is the most exposed. The smaller the amount of light becomes _ or more, the higher the sensitivity is, the higher the sensitivity is, and the rating is as follows. 〇: Less than 50mJ/cm2 △ : 50mJ/cm2 or more, less than 1〇〇mj /cm2 X: 100 mJ/cm2 or more (straightness evaluation) Regarding the pattern of the portion of the light-receiving sheet formed by the above method, the optical display is used as follows. The evaluation was performed by micro-mirror observation of ., , and page. Evaluation

〇: Good linearity △: Partial linearity defect X: Poor linearity (pattern shape evaluation) V m mask Evaluation. The cross-section of the cross-section is good by the electron microscopic observation of the section of the u: division pattern of the above-mentioned financial secretary. The rating is as follows: the cross section is a tapered shape X: the cross section is an inverse tapered shape (resolution evaluation) 323842 240 201233734 The pattern of the heart of the filter segment formed by the above method is used. Evaluation was performed by optical microscopy. Evaluation. It is as follows. A poor resolution means that the adjacent straight line pattern is a connection = a defect. The rating of the assessment is as follows. 5 ◎: Good resolution and linearity 〇: The linearity is slightly poor, but the resolution is good. △: Partial resolution is poor. X: Defectiveness of the hometown (difference assessment). When the smear is applied (4) When the development was performed twice as much as the time, the pattern thickness of the mask portion of the formed two-light portion was measured as compared with the pattern thickness of the pattern formed by the appropriate image. The rating of the assessment is as follows. ◎: film thickness difference within 20% 〇: film thickness difference is greater than 20%, within 40% △: film thickness difference is greater than 40% x: defect or flaking by 2 times imaging (anti-drug evaluation) will be by the above method The formed filter section was impregnated with N-mercaptopyrazine solution for 30 minutes, and then washed with ion-exchanged water and air-dried. For 100, the pattern of the mask portion was observed with an optical microscope. to evaluate. The rating of the assessment is as follows. ◎. Appearance, color, no change, good 〇: a part of wrinkles, but no change in color, good △: some color shedding 323842 241 201233734 χ: peeling or color shedding (evaluation of the stability of the coloring composition) The obtained photosensitive coloring composition was measured for viscosity at the initial stage and room temperature after one month, and the hometown was evaluated for the increase in viscosity of the initial viscosity. The rating is as follows. (Change rate of viscosity over time) =| [(Initial viscosity) - (time-dependent viscosity)] / (initial viscosity)|χ100«) ◎: The ratio of viscosity increase is more than 5% or less is good 〇: the ratio of viscosity increase is greater than 5 % and less than 10% X: The ratio of viscosity increase is greater than 10% [Table Dl 1 ] Table D-11 (Evaluation 1) Brightness Υ (Evaluation 2) Contrast (Evaluation 3) Crystallization (Evaluation 4) Sensitivity (Evaluation 5) Straight婊 (Evaluation 6) 9 Cable shape (Evaluation 7) Resolution (Evaluation 8) Resistance to imaging (Evaluation 9) Resistance to first product (Evaluation 10) & Stability Example 7 23.6 5250 〇〇〇❺ © 〇ο Example 8 23.5 5060 9 0 〇〇d 〇ο Example β 212 4980 9 〇0 0 &lt;9 0 ο Example 10 23^ 5030 〇0 〇〇〇&lt;9 0 ο Example Ή 23.1 5170 0 0 〇〇〇〇〇ο Example 12 23.Β 5030 ❺ 〇〇〇❹ 〇ο Example 13 24.8 4950 〇〇〇〇〇〇d ο Example 14 24.8 4810 〇〇〇〇〇β Φ ο 赏 Example 15 24.2 5110 0 0 0 0 〇d ο Example 1β 24.2 4920 〇〇〇〇〇〇ο ο Example 17 23&lt;3 5820 〇〇〇〇〇❺ ο Embodiment 18 23.5 5220 〇0 〇0 0 ο 贲Example 19 24.4 5640 〇〇0 〇〇ο ο Example 20 23.3 5460 〇〇〇0 @Example 21 25.0 4890 〇〇〇〇ο 〇ο ο 22 23.8 5070 ❺ 〇0 0 〇〇ο ο Example 23 23.3 4740 〇Ο ' 〇〇〇ο ο Example 24 24.0 5070 〇〇〇〇〇〇ο ο Real flower example 25 23.5 4930 〇〇0 0 〇ο ο 实 Example 2β 22.9 4Β20 ❸ 〇〇〇〇〇ο ο 实例27 23.0 5120 ❹ 〇〇〇〇❾ ο ο 实例28 23.6 4910 〇0 〇e &amp; ο ο Example 29 22.9 5290 ο 〇 〇〇Θ 11 ο ❹ Example 30 23.9 5020 〇〇〇〇ο Example 31 23.Θ 4750 ❾ 〇〇0 ο ο Mai test case 3 2Ζ2 4520 X 〇〇X 厶〇9 ο Mai test case 4 21.0 4550 Δ 〇〇〇〇〇Δ ο Reference Example 5 23.0 3290 Δ 〇0 0 〇〇d X Wheat test case 6 20.8 4470 X 〇Δ 厶〇ο ο Reference example 7 20.0 4480 〇〇Δ 〇〇〇厶9 Reference example 8 20.7 3400 厶Δ 厶〇〇厶ο ο Reference Example 9 21.7 4540 厶X X X X X X ο

242 323842 201233734 As shown in Table D-11, a color filter containing the pigment (A1) represented by the formula (1) and the resin (D-B1) having the constituent units (D to bl) to (D-b3) The coloring composition is evaluated at all levels to obtain a high level of evaluation results.

That is, in the combination with the pigment (A1), in the constitution of a constituent unit (Nbl) containing a large number of resins, the contrast is improved and the stability over time is determined, and a plurality of resins (D-b2) are contained. In the structure containing a large amount of resin (D-b3), it is seen that the result of suppressing the crystallization of the pigment in the heating step and the effect of suppressing the resolution can be suppressed. However, if any of the constituent units satisfy a specific content ratio, a photosensitive coloring composition having a high performance of 1 = a constituent unit ratio can be obtained, and a high-performance and well-balanced color crossing system can be obtained: ==: B-compound The combination of the sensitivity, the linearity, and the analyticity of the compound, wherein the photopolymerization initiator (D) is - 6-(2-mercapto-carbenyl, meta-bumin 1-[9-ethyl is incorporated into the photosensitive coloring composition, and it is more excellent in the image-forming property of the polyfunctional thiol. Excellent. The light-colored coloring composition is resistant to, and further contains ultraviolet light in the solution. Further, the photosensitive coloring composition of the agent in the photosensitive coloring composition of the absorbent further contains a storage stability system and is more excellent in stability over time. 323842 243 201233734 In addition, the photosensitive materials in Reference Examples 3 to 9 The coloring composition has a low brightness or contrast ratio, and the evaluation of the crystallization of the pigment in the heating step or the evaluation of the filter element with the sensitivity first is not good. (Production of color filter) The total amount of the pigment and the pigment derivative in the coloring composition (PR-1) was 4.39 parts, and it was changed to CI pigment green 58/CI pigment yellow 150=2. 63 parts in the green photosensitive coloring composition. 76 parts, in the blue photosensitive coloring composition, CI Pigment Blue 15:6/CI Pigment Violet 23=3.51 ® parts/0. 88 parts, the other pigments were prepared in the same manner as the pigment dispersion (P-3) In the dispersion, the pigment dispersion of the photosensitive coloring composition (RR-1) is changed to a pigment dispersion of each color to obtain a green photosensitive coloring composition for a color filter, and the color filter is colored with blue color. Composition. at lO The photosensitive substrate (RR-1) was coated with a thickness of about m on a glass substrate of Omm x 1000 mm by a die coating method, and the solvent was removed in an oven at 70 ° C for 20 minutes and dried. Then, an ultraviolet light was used by an exposure device. The stripe pattern was exposed. The exposure amount was 100 mJ/cm 2 . Further, the unexposed portion was removed by spray imaging using a developing solution composed of an aqueous solution of sodium carbonate, and then washed with ion-exchanged water and heated at 230 ° C. The substrate is formed into a red filter segment having a line width of about 50 for 30 minutes. Then, by the same operation, a green photosensitive composition is formed adjacent to the red filter segment to form a green filter segment, and then, A blue color filter was formed using a blue photosensitive coloring composition, and a color filter having three color filter segments was obtained on the same glass substrate. When the coloring composition for a color filter described above is used, a fine color calender having a color filter characteristic of 323842 244 201233734 and a red filter having excellent color characteristics and good heat retention can be produced. INDUSTRIAL APPLICABILITY According to an embodiment of the present invention, there is provided a pigment composition for a color filter which is excellent in brightness and contrast, and which is less likely to cause crystal precipitation of a diketopyrrolopyrrole pigment by a heating step. , a coloring composition, and a color filter using the same. [Simple description of the diagram] References None [Main component symbol description] None

323842 245

Claims (1)

201233734 VII. Patent application scope: 1. A diketopyrrolopyrrole pigment composition for a color filter containing a diketopyrrolopyrrole pigment represented by formula (1), and a formula (A-2) The color filter of the diketopyrrolopyrrole pigment shown is a diketopyrrolopyrrole pigment composition, and the content of the diketopyrrolopyrrole pigment represented by the formula (A_2) is diketopyrrole. The total mass of the pyrrole-based pigment is 1% by mass to 15% by mass based on the total mass; ^ (1) Formula (A-2) [In the formula (A-2), A and B are each independently a hydrogen atom, a fluorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, and may have a substituent. Phenyl, _CI?3, -SR2, -N(R3)R4, -C00R5, -C〇·, -C0NHR6, -C0N(R7)R8, -SO2NH2, -SO2NHR9, or -S〇2N (R1Q Ru, R to R are each independently a carbon group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent; but A and B are not simultaneously a hydrogen atom]. The color filter quinone ketone pyrrolopyrrole pigment composition according to claim 1, wherein the diketopyrrolopyrrole pigment represented by the above formula (A_2) is a formula (AK) , in the group consisting of (A_2_2), 323842 201233734 selected (A-2-3) and (A-2-4) CI CI Formula (A-2 2) Formula (A-2 - 1) C» Formula (A_2 - 3) CI [R1 y in the formula (A-2-3) and the formula (A-2-4) are each independently an alkyl group having a carbon number of from j to 12 or a phenyl group which may have a substituent]. 3. The color filter according to the second or second aspect of the patent, wherein the color filter is a ruthenium ratio π and a η ratio ruthenium pigment composition, wherein the pigment red 254 is further contained as a diketone D 嘻And a pigment of a dimercaptopurine-based pyrrole-based pigment for a color filter according to the third aspect of the invention, wherein a diketopylpyrazole-based pigment is used. The content of the diketone group V» represented by the formula (1) is more than 85% by mass to 99% by mass based on the total content of the fluorenylpyrrole pigment and the C.1. Pigment Red 254. The color filter according to Item 3 or 4 is a diketone group 323842 2 201233734 and is converted into a pigment composition, wherein the two-hole base material of the formula (1) is a scale pigment and c. 颜料. Pigment Red 254 The mass ratio is 2〇: 8〇 to 99: 卜6· - 彩彩(10) The light ketone is a diketone squamous pigment composition containing two squash pigments of the formula (1) and a formula (B) 2) The diketone-based fluorinated pigment coloring sheet is shown to have a mass ratio of the formula (1) to the formula (B_2). 97: 3-85 · 15; Formula (B-2) [In the formula (B-2), A and B are each independently a hydrogen atom, a fluorine atom, a chlorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, and may have a substituent. Phenyl, _Cp3, -OR, -SR2, -N(R3)R4, -C〇〇R5, _c〇NH2, -C0NHR6, -C0N(R7)R8, -SO2NH2, -SO2NHR9, or -SOzNCR1. Further, R to R11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aryl group which may have a substituent; but A and B are not simultaneously a hydrogen atom]. 7. The color filter according to claim 6, wherein the color filter is a diketone-based pyrrole pigment composition, wherein the above formula (B_2) is represented by the formula 323842 3 201233734 (B-2- 1), formula (B-2-2), formula (B-2-3), formula (B~2-4), (B-2-5), formula (B-2-6) and formula (B) -2-7) Selected from the group consisting of ^ Br Formula (B 2-1) Formula (B-2 2) Formula (B-2 - 3) ^ (B-2-4) [In the formula (B-2-4), the formula (b-2-6), and the formula (B-2-7), R12 to R15 are each independently a carbon group having 1 to 12 carbon atoms, or may have a substituent. Phenyl]. </ RTI> </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; 9. A coloring composition for a color filter comprising a coloring agent, a binder resin, and a coloring composition of an organic solvent, wherein the coloring agent is included in the scope of the patent application! To the second of the eight items - the two mentioned in the item and 323842 4 201233734 pyrrole pigment composition. 10. The coloring composition for a color filter according to claim 9, which further comprises a photopolymerizable monomer and/or a photopolymerization initiator. 11. A coloring composition for a color filter, comprising a pigment (A), a binder resin (CB), and a coloring composition for a color filter of a solvent, wherein the pigment (A) contains the formula (1) The pigment (A1) and the binder resin (CB) are alkali-soluble photosensitive resin (C-B1). (1) 〇12. A coloring composition for a color filter, which is a coloring composition for a color filter containing a pigment (A), a binder resin (DB), and a solvent, wherein the pigment (A) contains a formula (1) The pigment (A1) shown, the binder resin (DB) is a resin (D-B1) having a constituent unit (D-bl) to (D-b3), Br Br Formula (1) 323842 5 201233734 (D-bl) A constituent unit having a carboxyl group: 2 to 60% by weight/〇(D-b2) having an aromatic ring group represented by the formula (D-2) or (D-3) Constituent unit: 2 to 80% by mass (D-b3) a constituent unit having an aliphatic cyclic group represented by the formula (D-4) or (D-5): 2 to 60% by mass R Formula (D-3) [In the formula (D-2) and the formula (D-3), R is a hydrogen atom or an alkyl group having a benzene ring having 1 to 20 carbon atoms; in the formula (D-3) The dotted line portion represents a ring structure adjacent to a benzene ring and containing one or more saturated or unsaturated heterocyclic rings which may have a substituent] 323842 6 201233734 13. The coloring composition for a color filter according to the above-mentioned patent application, wherein the pigment (A) further contains at least one of a diketopyrrolopyrrole other than the pigment (A1). Pigments, azo pigments, quinone pigments, fluorene pigments, quinacridone pigments, benzimidazolone pigments, and quinoline pigments The selected group of members. The coloring composition for a color light-passing sheet according to any one of the above-mentioned claims, wherein the acetophenone-based compound and the phosphine-based compound are further contained in the coloring composition. The compound and the oxime ester compound are at least one selected photopolymerization initiator. A color filter comprising a color filter composition for a color filter according to any one of the preceding claims. 323842 7 201233734 IV. Designated representative map: (1) The representative representative of the case is: (). (There is no picture in this case) (2) The symbol of the symbol of this representative figure is simple: (none) 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: B type (1) formula (A-2) 323842 3