TW201111447A - Production method of pigment dispersion solution - Google Patents

Abstract

This invention discloses a production method of a pigment dispersion solution, including the step of uniformly dispersing dyes and pigments in the solvent simultaneously. According to the production method of this invention, the dyes includes at least one compound selected from the group consisting of azo compounds, metal complexes taking azocompounds as ligands, and xanthene compounds.

Description

201111447 VI. Description of the Invention: [Technical Field to Which the Invention Is Ascribed] The present invention relates to a method of producing a pigment dispersion liquid. [Prior Art] A pigment dispersion liquid used for a color filter or the like has been produced by, for example, dispersing a pigment, a dispersant, a resin, a viscosity reducing agent, a solvent, or the like (for example, a patent document). In the dispersion treatment herein, by controlling the dispersion mixing order of the respective components, that is, first, a large amount of viscosity reducing agent is adsorbed by a dispersing agent and then a pigment is added, the viscosity characteristics and stability thereof can be improved without adversely affecting the color characteristics. [Patent Document 1] JP-A-2003-327864 SUMMARY OF THE INVENTION However, a resist coating film containing a pigment dispersion obtained by the above method may generate foreign matter. Further, there is a problem that the brightness of the color filter is lowered depending on the additives used in the dispersion. SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing a pigment dispersion which can further reduce the generation of foreign matter and which is known as a color filter of a party. That is, the present invention provides the following [1] to [9]. [1] A method for producing a pigment dispersion, which comprises the step of uniformly dispersing a dye and a pigment in a solvent at the same time. [2] The production method according to [1], wherein the dye contains at least one selected from the group consisting of an azo compound, a metal complex having an azo compound as a ligand, and a ruthenium compound. [3] The production method according to [1] or [2], wherein the dye system contains the compound represented by the formula (1) 149310.doc 201111447 compound:

(In the formula (1), R to R are an aromatic furnace group independently representing a hydrogen atom, -R6 or a carbon number of 6 to 1 Å, and a hydrogen atom contained in the aromatic hydrocarbon group may pass through a halogen atom, ·r6, -OH ' -OR6 &gt; -S03- ' -SO3H ' -SO3M ' -C02H ' -C〇2r6 λ -S03R6, -S02NHR8 or -S02N(R8)R9 is substituted, R5 means -S〇3·, -S03H, -S03M , -C02H, -C02R6, _S〇3R6, -S02NHR8 or -S〇2N(R8)R9, m is not an integer of 0~5. When the claw is more than the integer, the plurality of Han 5 may be the same or different. X represents a halogen atom, a represents an integer of 〇 or 1, and R0 represents a saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, and -CH2· contained in the above saturated hydrocarbon group may be via -〇-, _co• or _"_substituted, R" represents a hydrogen atom or a carbon number of 1 to 4, and R8 and R9 each independently represent an alkyl group having a substituent of i~i〇, a carbon number which may have a substituent of 3~ a cycloalkyl group of 30 or _q, or ... and a ruler 9 may be bonded to each other to form a heterocyclic ring having a carbon number of a substituent, the above alkyl group and -CH2- contained in the above cycloalkyl group Can be replaced by -〇-,·(:〇_,·ΝΗ_ or -NR6a-, 149 310.doc 201111447 Q represents an aromatic heterocyclic group which may have a carbon number of 6 to 1 G of a substituent, or an aromatic heterocyclic group having a carbon number of 3 to 1 Å which may have a substituent, and Μ represents a nano atom or a potassium atom, and (1) The compound shown has a + charge number which is the same as the _ charge number. [4] The method of any one of [1] to [3], the method of the present invention, wherein the dye: pigment-1.99~ The mass ratio of 99:1 contains dyes and pigments. [5] The shearing method of any one of [1 J to [4], the woody r+» * <I^ method, wherein the pigment system is selected from C · I. Pigment Blue 15:6, CI 苜%I έ羊κ ^ τ . Yan 枓 Green 36, C.1. Pigment Green 58, CI Pigment Yellow 138, C 丄 Pigment Yellow 139, CI Pigment Yellow 15 〇, ci At least one of the group consisting of pigment red hydrazine, CI pigment red 242 and CL pigment red 254. The pigment system contains CI

[6J] The production method according to any one of [1] to [5], wherein the pigment blue is 15:6. A method for producing a coloring composition, which comprises the pigment dispersion obtained by the production method of (1) to (8): any one selected from the group consisting of a solvent, a tree sulfonium compound, a photopolymerizable compound, and a photopolymerization initiator. A step of mixing at least one of the constituent groups. The [8] coloring pattern obtained by the method is formed by using a coloring composition as manufactured in [7]. [9] - A shirt color filter 'which contains a color pattern as (9). Sheet 0 [1 〇 ( (4) crystal display device, (4) Color 遽 光 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Specially known dyes and pigments can be used. As the dye, hydrazine is preferably an organic solvent-soluble dye, more preferably a dye containing at least one selected from the group consisting of an azo compound, an azo compound as a ligand, and a compound composed of a compound. Furthermore, it is more preferably a wood containing one less one selected from the group consisting of the compounds represented by the following formulas (1) to (3). Here, the organic solvent-soluble dye refers to an age-sensitive dye which can be dissolved in the company. Μ As the dye, a dye containing an m compound is preferred, and a dye containing a compound represented by the formula (1) is more preferred.

(In the formula (1), R to R4 each independently represent a hydrogen atom, _R6 or an aromatic fluorenyl group having a carbon number of 6 to 1 Å. The hydrogen atom contained in the aromatic hydrocarbon group may pass through a _ atom, _R6, -OH , -OR6, _s〇3·, _s〇3H, _s〇3M, c〇2H, c〇2R6, _SC>3R6, -S〇2NHR8 or -S02N(R8)R9 are substituted; R represents -S〇3, _s 〇3H, -S03M, -C02H, -C02R6, -S〇3R6, _s〇2Nhr8 or -so2n(r8)r9; m represents an integer from 0 to 5. When the claw is an integer of 2 or more, plural &amp; 149310.doc 201111447 represents a halogen atom; a represents an integer of ^ or 丨; R represents a saturated hydrocarbon group having a carbon number of 1 to 10 which may have a substituent, and the -CHr contained in the above saturated flame group may be _〇_, _c〇• or _NR6a_substituted; R0a represents • a nitrogen atom or a slave number of 1 to 4; - R and a ruler respectively represent an alkyl group having a substituent of 1 to 10 carbon atoms, a cycloalkyl group having a carbon number of 3 to 3 fluorene having a substituent or _Q; or r^r9 may be bonded to each other to form a heterocyclic ring having a carbon number of 丨~丨〇; the above alkyl group and the above ring _CH2- contained in the alkyl group may be via _〇_, -c〇_, or -NR 6a-substituted; Q represents an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent or an aromatic heterocyclic group having 3 to 10 carbon atoms which may have a substituent; /, Μ represents a sodium atom or a potassium atom; The compound represented by the formula (1) has the same charge number as the _ charge number. Here, 'the aromatic hydrocarbon group' may, for example, be an aryl group, an aralkyl group, an alkyl group-substituted aryl group, etc. &quot;°, etc. Examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, and a phenanthryl group. Examples thereof include a aryl group, a phenyl group, a stupid ethyl group, a phenyl group, a triphenyl group, and a benzyl group. And a naphthylethyl group, etc. The aryl group substituted by the transradical group is arbitrarily combined with the above-mentioned aryl group and the alkyl group mentioned below. ^ As a halogen atom, fluorine, chlorine, bromine etc. are mentioned. The so-called saturated smog group can be: a ketone group, a cycloalkyl group, an alkyl group substituted by an alkyl group, or a cycloalkyl group-substituted alkyl group. Length 149310.doc 201111447 As a base, it can be listed as a base. Methyl, ethyl, propyl, isopropyl, butyl isobutyl, pentyl, isopentyl, neopentyl, hexyl, heptyl, octyl Base, "methylpropyl, 2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2-ethylhexyl, decyl, decyl, and Methyl n-propyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, etc. As a cycloalkyl group, it can be listed as a retort. Pentyl, cyclohexyl, % heptyl, cyclooctyl 'tricyclic fluorenyl, etc. As the heterocyclic group, it may be the right $. J $ has a scent of a scent. It may also be non-aromatic. As an aromatic heterocyclic group, it is exemplified:

-NH

As a heterocyclic ring having no aromaticity, it can be enumerated

V ?〇 ό

Ή

N η

0

Wait. Further, the heterocyclic group has an arbitrary position. In addition to the positions described above, the bond may be -OR6, and examples thereof include an oxygen-burning such as butoxyhexanyloxy, ethoxypropoxy, hexyloxy or 2-ethylhexyloxy. Base. 1493l0.doc 201111447 As -C〇2R6 ', methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, pentyloxycarbonyl , isopentyloxycarbonyl, neopentyloxycarbonyl, cyclopentyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, heptyloxycarbonyl, cycloheptyloxycarbonyl, octyloxycarbonyl, 2-ethyl Hexyloxycarbonyl, cyclooctyloxycarbonyl, decyloxycarbonyl, decyloxycarbonyl, tricyclodecyloxycarbonyl, methoxypropoxycarbonyl, ethoxypropylcarbonyl, hexyloxypropoxy A carbonyl group, a 2-ethylhexyloxypropoxycarbonyl group, a decyloxyhexyloxycarbonyl group or the like. Examples of the -S〇3R6 include a decyloxysulfonyl group, an ethoxysulfonyl group, a hexyloxysulfonyl group, and a decyloxysulfonyl group. As -SOiNHR8, there may be mentioned: an amine sulfonyl group, an N-(fluorenyl)amine sulfonyl group, an N-(ethyl)amine sulfonyl group, an N-(propyl)amine sulfonyl group, and an N (isopropyl)amine. Sulfonyl, N-(butyl)aminesulfonyl, N-(isobutyl)aminesulfonyl, N-(pentyl)aminesulfonyl, N-(isopentyl)aminesulfonyl, N-methyl Neopentyl)aminesulfonyl, N-(cyclopentyl)aminesulfonyl, N-(hexyl)aminesulfonyl, N(cyclohexyl)aminesulfonyl, N-(heptyl)aminesulfonyl , N_(cycloheptyl)amine sulfonyl, N-(octyl)amine sulfonyl, N-(2-ethylhexyl)amine sulfonyl, and (1,5-dimethylhexyl)amine sulfonate Sulfhydryl, N-(cyclooctyl)amine sulfonyl, N-(fluorenyl)amine sulfonyl, N-(fluorenyl)amine sulfonyl, N-(tricyclodecyl)amine sulfonyl, N ( Alkyloxypropyl)aminesulfonyl, N-(ethoxypropyl)aminesulfonyl, N(propoxypropyl)aminesulfonyl, N-(isopropoxypropyl)aminesulfonate Sulfhydryl, N_(hexyloxypropyl)amine sulfonyl, N-(2-ethylhexyloxypropyl)amine sulfonyl, N-(methoxyhexyl)amine sulfonyl, N-(3 -Phenyl_ι_methylpropyl)aminesulfonyl and the like. 149310.doc 201111447 Further, as -so2nhr8, it may be a group represented by the following formula. In the following formula, X1 represents a halogen atom. X3 represents an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, and the hydrogen atom of the alkyl group and the alkoxy group may be substituted by a halogen atom. X2 represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom or a nitro group, and a hydrogen atom of the alkyl group and the alkoxy group may be substituted by a halogen atom. The alkyl group having 1 to 3 carbon atoms which may be substituted by a halogen atom may be a trifluoromethyl group or the like in addition to the above alkyl group. The alkoxy group having 1 to 3 carbon atoms which may be substituted by a halogen atom may, for example, be the above alkoxy group, especially a decyloxy group, an ethoxy group or a propoxy group.

X^JK2 X^NHi〇2

149310.doc -10- 201111447

HO^k/NHSOj &gt;ss/is^NHS02 HO&quot; -NHS〇2

H〇^\/\^NHS〇2, NHS〇a

I I NHSO, NHS〇2 人八义 I HO&quot;^Y^NHS〇2 'NHSOz oh HO.

NHS〇2 HO

149310.doc -11 - 201111447

Me〇-NHS02

NHS〇2

X1 ~ "02 x1 ~ CF3CH2NHSO2 CF3(CF2)7CH2NHi〇2 Cl NHS〇2

'493l0.doc -12- 201111447

149310.doc -13- 201111447 As -S02N(R8)R9, the following bases can be cited:

Examples of the hetero ring formed by bonding R8 and R9 to each other include a group represented by the following formula:

149310.doc -14· 201111447

Further, the substituents of the alkyl group and the cycloalkyl group of R and R9 can be appropriately selected from the above respective structures, and examples thereof include a halogen atom, a trans group, _Q, -CH=CH2, -CH=CHR6 and the like. Wherein 'as R8 and R9, preferably an alkyl group having 1 to 1 carbon number, a cycloalkyl group having 5 to 7 carbon atoms, an allyl phenyl group having a carbon number of 8 to 10, and a carbon number of 2 〜8 hydroxy-containing alkyl and aryl, carbon 2 to 8 alkoxy-containing alkyl and aryl 'more preferably a carbon number of 6 to 8 branched alkyl, especially preferably 2-B Base group. The substituent of the aromatic hydrocarbon group having 6 to 10 carbon atoms is preferably ethyl, propyl, phenyl, dinonylphenyl, _s〇3r6 or _s〇2NHR8. Here, R8' in -SC^NHR8 is preferably an alkyl group having a carbon number (7) and a cycloalkyl group having a carbon number of 3 to 3 Å, more preferably an alkyl group having a carbon number of 丨~&quot; Preferably, it is a branched alkyl group having a carbon number of 6 to 8, and particularly preferably a 2-ethylhexyl group. ^93l〇.doc •15- 201111447 As the aromatic hydrocarbon group having 6 to 1 carbon atoms which may be substituted, a nonylphenyl group, a dinonylphenyl group, a trimethylphenyl group, an ethylphenyl group, Propyl phenyl, hexyl phenyl, nonylphenyl, fluorophenyl, phenyl, bromophenyl, hydroxyphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyl An oxyphenyl group, a decyloxyphenyl group, a trifluoromethylphenyl group, a biphenyl group, a dimethylphenylphenyl group, or the like, and a group obtained by further substituting ?s2NHR8 on the groups. Examples of the substituent of the aromatic heterocyclic group having 5 to 10 carbon atoms include an ethyl group, a propyl group, a phenyl group, a dimethylphenyl group, _s〇3R6 or _s〇2nHR8. Here, as R8 in -ShNHR8, an alkyl group having a carbon number of 1 及 and a cycloalkyl group having a carbon number of 3 to 30 are preferable, and an alkyl group having a carbon number of 丨~1 更 is more preferable, and further preferably A branched alkyl group having a carbon number of 6 to 8, more preferably a 2-ethylhexyl group. Further, examples of the substituent of the saturated hydrocarbon group of R6 include a halogen atom and an alkoxy group having 1 to 10 carbon atoms. Here, examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a pentyloxy group, an isopentyloxy group, and a neopentyloxy group. , hexyloxy, heptyloxy, octyloxy, b-propylpropoxy, decylpropoxy, methylbutoxy, 2-methylbutoxy, 3-f-butoxy-2-ethylhexyloxy, Alkoxy group, decyloxy group, bisdimethylpropoxy group, 12-dimethylpropoxy group, 2,2-dimethylpropoxy group and the like. In the compound represented by the formula (1), it is preferred that at least one of the ruler 1 and the ruler 2 or at least (10) of R3 and R4 is a burnt group of carbon number 4 or a carbon of 6 to 10 which may be substituted. Aromatic hydrocarbon group. It is preferably at least one of R^R2, and at least one of R3 and R4 is an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 1 carbon atoms which may be substituted. Further preferably, at least one of R1 and R2 is "solid", and at least one of R3 and r4 is an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms. R5 is preferably a carboxyl group. Ethoxycarbonyl, sulfonate, N-(2•ethylhexyloxypropyl)amine sulfonyl, N_(1,5-dimethylhexyl)amine sulfonyl, (3_phenyl_1 _Methylpropyl)amine oxime, N_(isopropoxypropyl)amine continuation base. The compound of the formula (1) is preferably selected, for example, from the formula (M) to the formula (I4). At least a compound of the group consisting of:

(In the formula (1 -1)~(1 -4), R, R, R13 ' R14 八知丨抚 a .in^ .. The knife independently represents a hydrogen atom, _R6 or carbon number ^, °Haifangxiang The hydrogen atom contained in the hydrocarbon group may be __ u 〇R, -S〇3-, -S03H, -S03Na, -C02H, -C〇2r6, one R15* - ^ e 3 , -S〇2NHR8 or -so2nr8r9 Substituted; K is not a gas atom, - c 3, _s 〇 3H, - s 〇 2nhr8 or - so2N (R8) R9;

K clothing is not ea TT r21 R24 八, 3, -S 〇 2NHR8 or -S02N (R8) R9; R ~ R knife independently means hydrogen sheet wind mat, -R 6 or carbon number 6~10 of 1 valent 149310. Doc -17· 201111447 An aromatic hydrocarbon group in which a hydrogen atom contained in the aromatic hydrocarbon group can pass through a functional atom,

-C02H, -C〇2R26, -so3h, -so3r26 or -S02NHR28 substituted; R25 represents -S03-, _S〇3Na, _C〇2h, _c〇2R26, 8〇 or so2nhr28; R26 represents carbon number 1~10 a monovalent saturated hydrocarbon group in which a hydrogen atom contained in the saturated hydrocarbon group may be substituted with an alkoxy group having 1 to 10 carbon atoms or a halogen atom; R represents a hydrogen atom, -R26, -CC^R26 or a carbon number of 6 to 1? An aromatic hydrocarbon group. The hydrogen atom contained in the aromatic hydrocarbon group may be substituted by -R26 or _OR26; and R31 and R32 each independently represent a monovalent aromatic hydrocarbon group having 6 to 1 carbon atoms, preferably benzene 2 a hydrogen atom contained in the aromatic hydrocarbon group may be substituted by a _ atom, -R26, -OR26, -C〇2R26, -S03R26 or -S02NHR28; 3 3 R represents _s〇3_4-so2nhr28; R represents hydrogen Atom, _s〇3_ or _s〇2nHr28; R and R each independently represent a monovalent aromatic hydrocarbon group having 6 to 1 carbon atoms, preferably a phenyl group, and a hydrogen atom contained in the aromatic hydrocarbon group may be passed through - R26 or -S02NHR28 is substituted; R is not ~s〇3- or -S02NHR28; R6 'R8, p 9 _ Formula U-1)~ The number of d-charges shown in formula (1-4) are the same. Among them, the formula (1_4) is preferred. The compounds 4 K, m, x and a represented by the formula (1) have the same meanings as described above). The number of + charges in the compound of the compound, wherein the compound is, for example, a compound of the formula (la) to (lf) 149310.doc 201111447. Wherein, the number of + charges and the number of charges in the compound of the formula (lf) are the same:

Wherein Rb and Re each independently represent a hydrogen atom, _S〇3-, _C〇2H or -S02NHRa;

Rd, Re, and R/ respectively represent ·S〇3-, _s〇3Na or _S〇2NHRa;

Rg, Rh and R1 each independently represent a hydrogen atom, _S〇3·, _S〇3H or -S02NHRa;

Ra represents an alkyl group of 1 to 10, preferably 2-ethylhexyl; X and a represent the same meanings as described above. 149310.doc -19- 201111447 Formula 〇b) The compound of π is a compound represented by formula (5). Tautomers. Among them, a compound represented by the formula (5) and a compound represented by the formula (lf) are preferred. The compound represented by the formula (1) can be chlorinated, for example, by a conventional method, by chlorinating the pigment or the pigment intermediate, and the obtained pigment or pigment intermediate having the s〇2ci and the amine represented by r8-nh2 Manufactured by reaction. In addition, the pigment produced by the method described in the method of the right-hand side-to-left bottom of page 3 of the Japanese Patent Laid-Open No. Hei 3_787() No. 2, is vaporized in the same manner as described above, and then reacted with an amine to produce. The dye is preferably a dye containing an azo compound, more preferably a dye containing a compound represented by the formula (2): R510 R52~'N^f-A°~N=N-B° (2) (2) wherein 'A° represents a divalent aromatic nicotine group having 6 to 14 carbon atoms which may have a substituent; The B table may not have a carbon atom number of 6 to 14 of a substituent, or a valence aromatic heterocyclic group having a carbon number of a substituent; the second table: a gas atom, which may have a substituent The carbon number Η one or two or a thiol group having a carbon number of 2 to 18 which may have a substituent; R52 represents a hydrogen atom or a monovalent organic group]. The compound represented by the formula (2) is preferably a compound represented by the formula (2. :: 149310.doc 201111447 (2-1) βΜ|==ν· [(), ζ, ζ2 and Ζ3, respectively, may have a divalent aliphatic hydrocarbon group having 1 to 16 carbon atoms of the substituent, -CH2- contained in Ζ1, Ζ2 and Ζ3 may be substituted by -CO- or -〇-; R53 and R54 each independently represent a hydrogen atom and may have a substitution a monovalent aliphatic hydrocarbon group having 1 to 16 carbon atoms, or a fluorenyl group having 2 to 18 carbon atoms which may have a substituent; A and octagonal independently represent a divalent aromatic having a carbon number of 6 to 14 which may have a substituent a group of a hydrocarbon group; and a B group independently represent a valence aryl group having 6 to 14 carbon atoms which may have a substituent, n or a monovalent aromatic heterocyclic group having a carbon number of 3 to 14 which may have a substituent]. Each of B independently represents a carbon number which may have a substituent, and a carbon number of the divalent aliphatic hydrocarbon group of carbon number 16 is not a carbon number of the substituent, and the number thereof is preferably 2 to 1. 〇, more preferably 2 to "2, a divalent aliphatic nicotine group having a slave number of 1 to 16, and a dibasic carbon group may be mentioned, and examples thereof include a methylene fluorene 6 group, a propyl group, a butyl group, a group, and Dihexyl, heptyl, and bis Its octagonal hexa-heptanediyl group, the earth, the fluorenyl group, the tetradecanediyl group and the octa- or oxo-substituted in the carbon number valent aliphatic hydrocarbon group. The cNI6 aliphatic hydrocarbon group is substituted with a functional atom. The atom of the atom can pass through the gas source ^Z1 and Z2, preferably the number of the rabbits which can contain _〇·1 to 8, more preferably 149310.doc • 21·201111447: the carbon number is 5~7 Alkanediyl. As a preferred group, for example, it may be listed or even tuned. (ch^-〇-(ch2)2-o-(ch2)2-Z3 preferably has a carbon number of 1) The octavalent aliphatic hydrocarbon group of ～8 is more preferably an unsubstituted dienyl group of carbon number 8 , more preferably an unsubstituted dialkyl group of carbon number. As a preferred group, for example, (CH2)2_, -(CH2)4- or -CH2-C(=CH2)-. Indicates the carbon number of R53 and R54. The valence aliphatic group can be a straight bond, a branch or a ring. Any one of the carbon atoms of the aliphatic group does not include the carbon number of the substituent, and the number thereof is preferably 6 to 1 Å, more preferably 丨 4 to 4. As the monovalent aliphatic hydrocarbon group having 1 to 16 carbon atoms, For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and second Butyl, methylbutyl (U'3,3-tetramethylbutyl, etc.), methylhexamidine 5_dimethylhexyl, etc.), ethylhexyl (2-ethylhexyl, etc.), cyclopentyl, Cyclohexyl, nonylcyclohexyl (2-methylcyclohexyl, etc.) and cyclohexylalkyl. The hydrogen atom contained in the fluorene aliphatic hydrocarbon group having 1 to 16 carbon atoms may be substituted with an alkoxy group or a carboxyl group having a carbon number. Examples of the monovalent aliphatic hydrocarbon group having 1 to 16 carbon atoms which are substituted by the alkoxy group of carbon number 8 include a propoxypropyl group (3-(isopropoxy)propyl group, etc.) and an alkoxypropyl group. (3-(2-ethylhexyloxy)propyl, etc.). The aliphatic hydrocarbon group having 1 to 16 carbon atoms which is substituted by a carboxyl group may, for example, be a 2-(carboxy)ethyl group, a 3-(carboxy)propyl group or a 4-(carboxy)butyl group. The hydrogen atom contained in the fluorenyl group of the inverse of 2 to 18 may be substituted with an alkoxy group having a carbon number of 丨8. The carbon number of the fluorenyl group having 2 to 18 carbon atoms which may have a substituent is counted by the carbon number of the substituent, and the number thereof is preferably 6 to 1 Å. Examples of the fluorenyl group which may have a substituent I49310.doc • 22-201111447 methoxybenzimidate include an ethyl hydrazide group, a fluorenyl group, a benzyl group (p-methoxyphenyl fluorenyl group, etc.).

As R53 and R54, it is a sulfonium atom, a monovalent aliphatic hydrocarbon group having a slave number of 1 to 4, and a fluorenyl group having 2 to 5 carbon atoms. As a base of the phlegm, the hydrogen atom, the ethyl sulfonyl group or the propyl fluorenyl group can be mentioned. Examples of the divalent aromatic nicotyl group having 6 to 14 carbon atoms which represent A1 and A2 include a phenylene group and a naphthyldiyl group. Among them, a phenyl group is preferred. Examples of the substituent of the divalent aromatic (tetra) group having 6 to 14 carbon atoms include a sulfonyl atom, a carbon atom of IU -8, a oxy group of carbon number 8, an acid group, an acid group, and an amine sulfonate. And N-substituted amine sulfonyl groups and the like. Examples of the dentate atom include a gas atom, a (tetra), a (tetra), a (tetra), and the like, and a fluorine atom, a gas atom or a bromine atom is preferred. Examples of the alkyl group having 1 to 8 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, second butyl group, tert-butyl group, pentyl group and hexyl group. Preferably, it is an alkyl group having a carbon number of 44, more preferably an alkyl group having a carbon number of 丨~2, and particularly preferably a methyl group. Examples of the alkoxy group having 1 to 8 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a second butoxy group, and a third butoxy group. The group, the pentyloxy group, the hexyloxy group and the like are preferably an alkoxy group having a carbon number of 丨4 or more, more preferably an alkoxy group having a carbon number of 1 to 2, and particularly preferably an anthraceneoxy group. The N-substituted amine sulfonyl group may be exemplified by ss2Nhr8 and -s〇2N (r8) in the compound represented by the formula (1). R9 is the same as the ones listed above. Among them, it is preferred that the ruler 55 and the Han 56 are independently an aliphatic hydrocarbon group having a carbon number of 丨~丨6 which may have a substituent, or may be I49310.doc -23. 201111447 has a substituent a group of sulfhydryl groups having a carbon number of 2 to 18, and B2 each independently represent a carbon number aromatic aromatic group which may have a substituent, or a carbon number of 3 to 14 valent aromatic which may have a substituent Examples of the monovalent aromatic hydrocarbon group having a carbon number of 6 to 14 and a heterocyclic group include a phenyl group and a naphthyl group. The valent aromatic heterocyclic group having a carbon number of 3 to 14 may be exemplified below.

0 0 ^ [R represents a hydrogen atom or a rhodamine]. a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms and a monovalent aromatic heterocyclic group having 3 to 14 carbon atoms; the hydrogen atom contained may be a hydroxyl group, a pendant oxy group, a carbon number aliphatic hydrocarbon group, a cyano group or an amine group Substituent or N-substituted amine group.曰 As the hydrazine-substituted amino group, _NHR57 group or Νν, 58 group is preferred. And Μ7 and R58 each independently represent a carbon number 取代 which may have a substituent “ “ “ : 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪 肪The monovalent aliphatic hydrocarbon group having 1 to 16 carbon atoms and the monovalent aromatic heterocyclic group having 3 to 14 carbon atoms are the same as those described above. B and B are preferably independently of the formula (2-1 a). The base shown: 149310.doc -24· 201111447

(2-1a) [wherein 'r59 in the formula (2-la) represents a hydrogen atom or a monovalent aliphatic hydrocarbon group having a carbon number of 丨~16 which may have a substituent; y represents a carbon number 丨~16 which may have a substituent 1 valent aliphatic hydrocarbon group]. The formula shown in formula (2-1 a) is brewed!疋 丨 丨 衣 can be a ketone type, or an enol type. The anthracene aliphatic hydrocarbon group having a μ carbon number of 1 to 16 is preferably the same as the above, and preferably a mercaptobutyl group (1,1,3,3-tetradecylbutyl group or the like) or a methyl group (1). '5--decylhexyl, etc.), ethylhexyl (2 ethylhexyl, etc.), nonylcyclohexyl (2-fluorenylcyclohexyl, etc.) and alkoxypropyl (3_(2-ethylhexyloxy) a propyl group or the like, such as a branched aliphatic hydrocarbon group. R is preferably a methyl group. Examples of the compound represented by the formula (2) include a compound represented by the formula (1-1) to the formula (1-18). The bond on the right side of A1, A2, Ζ丨 and Ζ2 in the table indicates that it is close to Ζ3. key:

149310.doc 25· 201111447 [Table l] 1-1 A1 A2 Z 1 z 2 Present-Or R59 R59' R60 R60' -c2h5 -c2h5 —ch3 —ch3 R 5 3 R54 z3 —Η —H _(CH2)2 — z2 side z1 side [Table 2] 1-2 A1 A2 Z 1 z2 H3C h3c R59 R59' R60 R60' -c4h9 - C4H9 —ch3 A ch3 R53 R 54 z3 ——H ——H ——(CH2)2 Z2 side z1 side [Table 3] 1-3 A1 A2 z 1 z 2 h3c h3c -ύ- R59 R59' R60 R60' -c4h9 &quot;C4H9 —ch3 —CH3 R53 R54 z3 VH3 0 VH3 0 -(CH2)8 — Z2 side z1 side 26- 149310.doc 201111447 [Table 4] 1-4 A1 A2 Z 1 z 2 ch3 ch3 Good R59 R59' R60 R60' -C4H9 -c4h9 —ch3 —ch3 R53 R54 z3 ——Η —H —— (CH2)8 — z2 side z1 side [Table 5] 1-5 A1 A2 Z 1 z2 ch3 ch3 Or ch3 ch3 R59 R59' R60 R60' -c4h9 -C4H9 —ch3 —ch3 R 5 3 R54 z3 —H —H — (CH2)4 — z2 side z] side [Table 6] 1-6 A1 A2 Z 1 z2 ch3 ch3 ch3 ch3 R 5 9 R59' R60 R60, , ch3 , ch3 —ch3 —ch3 R53 R54 z3 ——H —H ——(CH2)8 — z2 side z1 side 27- 149310.doc 201111447 [Table 7] 1 — 7 A1 A2 Z 1 z2 ch3 ♦ ch3 ch3 ch3 R59 R59, R60 R60' , ch3 CH3 —ch3 —ch3 R53 R54 z3 —Η —H —(CH2)4—z2 side z1 side [Table 8] 1-8 A1 A2 Z 1 z2 ch3 ch3 ch3 R59 R59· R60 R60· CH3 CH3 -c2h5 - C2h5 R53 R54 z3 —H —H —(CH2&gt;8 – z2 side z1 side [Table 9] 1-9 A1 A2 Z 1 z2 ch3 ch3 ch3 ch3 R59 R59' R60 R60. ^ch3 0 ^ch3 0 —CH3 — Ch3 R53 R54 z3 —H —H —(CH2)4 — Z2 side Z1 side -28- 149310.doc 201111447 [Table 〇]

1-10 A1 A2 Z 1 z2 ch3 4 ch3 ch3 ch3 R59 R59, R60 R60, ^ch3 0 ^CH3 0 —ch3 —ch3 R53 RS 4 z 3 ——H ——H ——(CHaJe—z2 side z1 side [ Table 11] I - 1 1 A1 A2 Z 1 z 2 P R6 1 R61' R6 2 R62, —ch3 —ch3 —CH3 —ch3 R53 R54 z 3 —H ——H —(CH2)2 — z2 side z] side 29- 149310.doc 201111447 [Table 12] 1 — 12 A1 A2 Z 1 z 2 h3c h3c -3⁄4- R6 1 R61, R62 R62' -^^och3 ~^^-〇CH3 -c4h9 -c4h9 R 5 3 R 54 z 3 ——Η —H —(CH2)4 — z2 side z1 side [Table 13] 1 — 13 A1 A2 z 1 z2 h3c h3co_^ R61 R61' R62 R62' -Q-co2c2h5 -c3h7 -c4h9 R53 R54 z3 VCH3 0, ch3 0 ——(CH2)8—z2 side z1 side [Table 14] 1 — 14 A1 A2 z 1 Z2 ch3 ch3 R 6 1 R61' R62 R62, —^^*och3 ~^^·〇〇Η3 - C4H9 -c4h9 R53 R54 z 3 Y&quot;CH3 0 Y&quot;CH3 0 ch2 z2 side z1 side •30· 149310.doc 201111447 [Table 15] 1 — 15 A1 A2 z 1 z2 ch3 ch3 -a- R6 1 R61, R62 R62 , —^^~och3 —^^och3 -c4h9 -c4h9 R53 R54 z3 V&quot;ch3 0 V^ch3 0 Ύ^· ch2 Z2 side Z1 side [Table 16] 1 — 16 A1 A 2 Z 1 z2 ch3 ch3 Ό- ch3 R6 1 R6X, R62 R62' —^^-och3 -〇-〇ch3 -C4H9 -c4h9 R53 R 54 Z3 —H ——H ——(CH^s—r z2 side z1 side

Rw·

OH

=N

A1

HO 149310.doc -31 · 201111447 [Table 17] 1 - 17 A1 A2 z 1 z 2 Cl Cl R53 R54 R63 R63, —Η —H —ch3 —ch3 Ζ3 —(CH^ — ζ2 side ζ1 side r64,hn

—A1—N

HR64 ResH

[Table 18] 1-18 A1 A2 Z 1 z2 ch3 ~ύ~ ch3 R64 R64' r65 R65' -o R53 R54 z3 —H —H ——(CH2)8−% z2 side z1 side

R^HN-^ N=l OH OR54 Ο O RwO N-A2-眷一A-Ζ2-Ο—(ϋ—Ζ3一ΐ一Ο-*Ζ1-Ν-^-Α1&quot;&quot;Ν=Ν

NHRe6 I493l0.doc -32- 201111447 [Table 19]

1-19 A1 A2 Z 1 z 2 General ~Q~ R53 R54 R66 R66' ——Η——H ——H ——H Ζ 3 —(CH2&gt;8—Ζ2 side Ζ1 side [Table 20]

1-20 A1 A2 Z 1 z 2 Let R 5 3 R 5 4 z3 —H ——H —(CH2)8 — z2 side z1 side [Table 21] 1 — 21 A1 A2 z 1 z 2 Let R53 R 54 Z3 —H —H —(OH^e — z2 side z1 side-33- 149310.doc 201111447 5 preferably: B1 and B2 are the same type of base, and more preferably V and ', RZ and Z are the same type respectively. If it is such a group, the compound represented by the formula (2-1) can be easily produced. The compound represented by the formula (5)) can be obtained by using a compound represented by the formula (I-A) and a formula (in the solvent). The compound represented by Ι-A1) and the compound represented by the formula (IB) are in the range of 0 to 150. (: Manufactured under the reaction: Η一〇—21- R530 I it ~N-S-A1—N=N—B1 (IA) 0 Η—〇—22- RS4〇-N—S—A2—N=N —B2 (I-A') δ 〇Λ» 0 R67-C—23-C-Rw (IB) [Formula (IA), Formula (Ι·Α'), and Formula (IB), Ζι, z2, Z3 And r53, r54, A, A2, b1 and b2 have the same meanings as defined above; R67 and R68 each independently represent -OR69 or a dentate atom; and R11 represents an aliphatic hydrocarbon group having an i-valent carbon number of 1 to 16]. Dimethyl dicarboxylate, succinyl-ethyl ester, and propylene dioxime, as a compound represented by the formula (IB), examples thereof include isobutyl phthalate, dimethyl adipate, and amber azelate. Dichloro, octyl chloride, etc. The amount of the compound represented by the formula (IB) is compared with the total amount of the compound represented by the formula (IA) and the compound represented by the formula (Ι-A'). Preferably, it is 〇5 to 3 mol. Further, when water is contained in the solvent, it is preferred to use a compound represented by the formula (IB) in excess of the above amount. The compound represented by the formula (IB) The case where R31 and R" are -〇R33 J 平乂149310.doc -34- 201111447 4 is Tim An acid catalyst known as A. Examples of the acid catalyst include sulfuric acid, p-toluene acid, etc. The amount of the acid catalyst used is (4) the total of the compound represented by the formula (I_A) and the compound of the formula (IA). 1 mol is preferably (4). The compound represented by the formula (Ι·Α) and the compound represented by the formula (Ι-A,) and the compound represented by the formula (IV) are reacted in a solvent. For example, slaves are ethers such as 纟'Μ_dioxane (especially cyclic ethers); chlorine: methyl chloride, carbon tetrachloride, dichloroethane, diethylene glycol, trichloroethylene, perchloroethylene Diluted, dichloropropanol, chlorpyrifos, 1,2-two deserts, etc., such as sputum k-type propyl hydrazine, methyl isobutyl _, cyclohexanyl and the like; benzene, Abenben Carbon-based aromatics; N,N-dimethyl decylamine, N,N_: carbamide, N,N-methyl ethanoamine, N-methyl hydrazine, etc. It is also possible to use two or more solvents in combination with a guanamine or the like. The amount of the solvent used is preferably 丨~" with respect to the total amount of the compound represented by the formula (I_A) and the compound represented by the formula (?). Part by mass. More preferably 2 〜1〇质量份。 The compound of the formula (Ι-A) and the compound of the formula (I_A), and the compound of the formula (I'B) are preferably reacted under a nitrogen atmosphere or argon gas. The reaction can be carried out under the environment, and the reaction can be carried out under air-cooled air. The reaction temperature is, for example, preferably 〇15 to 15 generations, more preferably 1 〇 to 13 passages. The reaction time is preferably, for example, a bubbly hour. The order of addition of the compound represented by the formula (Ι-A), the compound represented by the formula (I_A), the compound represented by the formula (b), and the solvent is not particularly limited, and is preferably A compound represented by the formula (I-B) is added (dropwise) to a mulch containing a compound represented by the formula (IA), a compound represented by the formula (Ι-A), and a solvent. In the case of using the acid catalyst U9310.doc -35-201111447, it is preferably added to a solution containing a compound represented by the formula (IA), a compound represented by the formula (J_Ai), an acid catalyst, and a solvent. Add a compound of the formula). The method of obtaining the compound represented by the formula (2 1) as the target compound from the reaction mixture obtained in the above manner is not particularly limited, and various known methods can be employed, for example, by extracting the reaction mixture with an organic solvent, and purifying, Further, purification may be further carried out by a known method such as washing or recrystallization using an aqueous alkaline solution or an acidic aqueous solution. Further, the compound represented by the formula (2-1) can be produced by a coupling reaction of a compound represented by the formula (IC), a compound represented by the formula (IV) and a compound represented by the formula (IV), (). The formula (2) can be produced by reacting a salt of the compound represented by the formula (IV) with a compound represented by the formula (I-D) and a compound represented by the formula (Μ)), for example, in an aqueous solvent. -1) Compound shown: N=N—A2- Θ Ο II S- II Ο «?54 〇〇Z2—Ο—C—7?—c- R53〇°^21-ns-a1-nsn 〇10 X· (IC) H—B1 (ID ) H—B2 (ID· &gt;

R R· V , A2 , B1 (in the formula (1-C) and the formula (i-D), z1, Z2, z: and B have the same meanings as described above; 1 represents an inorganic or organic anion). Examples of the inorganic or organic anion of the compound represented by the formula (Ι-C), and the inorganic or organic anion, can be exemplified by a mouse compound ion, a vaporized ion bromide ion, an iodide ion, a perchloric acid ion, and hypochlorous acid. Ions, ions, 卞CH3-C00·, Ph c〇〇., etc., 149310.doc -36 · 201111447 Suppliers: 肖车乂佳 is a metal containing a ruthenium compound as a ligand; More preferably, it is a dye containing the compound represented by formula (7). The compound of formula T is a chromium cation anion or a salt of a cobalt cation anion and a cation:

More enumeration of vapor ions, desert ions, cH3_c〇〇·. In the formula (3), R to R 8 each independently represent a hydrogen atom, a halogen atom, a monovalent aliphatic hydrocarbon group having a carbon number, a nitro group, a phenyl group, _s〇2NHRa3Q, jo〆 or COORa31; R and Ra2. Respectively represent a hydrogen atom, a methyl group, an ethyl group or an amine group; R and R respectively represent a hydrogen atom, a monovalent hydrocarbon group having a carbon number of 1 to 1 fluorene, and a _CH 2 · contained in the s-xyl hydrocarbon group may be passed through or C〇-substituted; M1 represents Cr or Co; η1 represents an integer of 1 to 5; D1 represents a hydrogen cation, a monovalent metal cation or a monovalent cation derived from a compound having a p-mountain skeleton. Examples of the monovalent aliphatic hydrocarbon group having a carbon number i to 8 represented by Ral to Ra18 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and second butyl group, and 149310.doc-37· 201111447 tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, decyl, decyl butyl, 1,1,3,3-tetramethylbutyl, ls5-dimethylhexyl, - dimethyl heptyl, 2-ethylhexyl and iota, ι, 5,5·tetramethylhexyl and the like. As the carbon number of the expression and heart. The valence (four) may be exemplified by a mussel aliphatic group having a carbon number of 1 〇, a glycerol group having a carbon number of gqoii, an aromatic hydrocarbon group having a carbon number of 6 to 7 (7), and a carbon number of the combination thereof* The base of ~(7). The monovalent aliphatic hydrocarbon group having a carbon number is the same as the above, and the valence-valent aromatic hydrocarbon group having a carbon number of 6 to 1 Å is the same as the group represented by the formula (the compound represented by υ). Examples of the alicyclic alicyclic hydrocarbon group having a carbon number of 3 to 1 Å include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cyclodecyl group and the like.

Ra32-〇-Ra33, -Ra32-c〇-〇_R is substituted as -CH2- to the above hydrocarbon group of _〇_ or _c〇_, which can be listed

Ra32-0-CO-R a33 a33

Ra32 is a divalent aliphatic hydrocarbon group of carbon number 8, and Ra33 is a carbon number HU aliphatic aliphatic group. Examples of the divalent aliphatic hydrocarbon group having a carbon number of 1 to 8 of 32 include an anthracenylene group, an ethylidene group, a propane, a tert-1,3-diyl group, a propane·1,2-diyl group, and a butane-M-diene group. Base, butane-1'3-diyl, pentane deca-diyl, hexane decadanyl, heptane-l,l-diyl, octane-oxime, 8-diyl and the like. Examples thereof include a methoxymethyl group, an ethoxymethyl group, an oxycarbonyl group, a decyloxyethyl group, an ethoxyethyl group, a propoxyethyl group, a methyl lactyl group, and an ethoxy group. Base, propoxypropyl, 2·oxy _4-methoxyl: octyloxypropyl, 3-ethoxypropyl, 3-(2-ethylhexyloxy)propyl and the like. 149310.doc •38· 201111447 As -Ra32-CO-〇-Ra33 'may be exemplified: methoxycarbonylmethyl, decyloxycarbonylethyl, ethoxycarbonyl fluorenyl, ethoxycarbonylethyl, propoxy Carbocarbonyl fluorenyl, propoxycarbonylethyl, butoxycarbonylmethyl, butoxycarbonylethyl and the like. Examples of -Ra32-0-C0-Ra33 include an ethyl methoxy fluorenyl group, an ethyl ethoxyethyl group, an ethyl carbonyloxymethyl group, an ethyl carbonyloxyethyl group, and a propylcarbonyloxy fluorenyl group. And propylcarbonyloxyethyl, butylcarbonyloxymethyl, butylcarbonyloxyethyl and the like. As -S〇2NHRa3Q, an amine terminus; N-methylamine% thiol, N-ethylamine thiol, N-propylamine sulfhydryl, N-isopropylamine sulfonyl , N-butylamine sulfonyl, N-isobutylamine sulfonyl, N-tert-butylamine sulfonyl, N-t-butylamine sulfonyl, N-pentylamine sulfonyl , N-(l-ethylpropyl)amine sulfonyl, dimethyl propyl) amide, N-(l,2-dimethylpropyl)amine sulfonyl, n-(2, 2-Dimethylpropyl)aminesulfonyl, N-(1-methylbutyl)aminesulfonyl, N-(2-methylbutyl)aminesulfonyl, Ν·(3-methylbutyl Amine sulfonate, Ν·cyclopentylamine sulfonyl, Ν-hexylamine sulfonyl, Ν-(1,3-dimethylbutyl)amine sulfonyl, Ν_ (3,3- Nonylbutyl)amine hydrazino, hydrazine-heptylamine fluorenyl, Ν_(ι-methylhexyl)amine sulfonyl, N-(l,4-dimethylpentyl)amine sulfonyl, Ν_octylamine sulfonyl, Ν-(2-ethylhexyl)amine sulfonyl, Ν_(1,5-dimethyl)hexylamine sulfonyl, N-(l,l,2,2- Alkyl sulfonyl group, fluorenyl-allylamine sulfonyl group, etc. substituted by an aliphatic hydrocarbon group ; Ν-(2. methoxyethyl)amine sulfonyl, ν-(2-ethoxyethyl)amine sulfonyl, N-(1-methoxypropyl)amine acid group, ν -(3-decyloxypropyl)amine continued 149310.doc •39· 201111447 fluorenyl, N-(3-ethoxypropyl)amine sulfonyl, N-(3-propoxypropyl)amine Sulfonyl, N-(3-isopropoxypropyl)amine sulfonyl, n-(3-hexyloxypropyl)amine sulfonyl, N-(2-ethylhexyloxypropyl) Aminesulfonyl, n-(3-tert-butoxypropyl)amine sulfonyl, N-(4-octyloxy)amine sulfonyl, etc. substituted with -R31-0-R32 Sulfhydryl; N-(methoxycarbonylmethyl)amine sulfonyl, N-(methoxycarbonylethyl)amine sulfonyl, N-(ethoxycarbonylmethyl)amine sulfonyl, N_( Ethoxycarbonylethyl)aminesulfonyl, N-(propoxycarbonylfyl)aminesulfonyl, n-(propoxymethyl)aminesulfonyl, N-(butoxycarbonyl) Amine sulfonyl, N-(butoxymethylethyl)amine, hydrazino, etc., substituted with _r31_C〇_〇_r32, amine oxonium; N-(ethyloxyindenyl)amine sulfonate (Ethyloxyethyl)amine sulfonyl, N-(ethylcarbonyloxyanthracene Aminesulfonyl, N_(ethylcarbonyloxyethyl)amine hydrazide, N-(propylcarbonyloxyindenyl)amine sulfonyl, N-(propylcarbonyloxyethyl)amine Amine substituted by _r3i_〇_C〇_r32, such as sulfonyl, N.(butylcarbonyloxyindenyl)amine sulfonyl, N-(butyl-tert-oxyethyl)amine Sulfhydryl; N•cyclohexylamine sulfonyl, N-(2-mercaptocyclohexyl)amine sulfonyl, N-(3-decylcyclohexyl)amine sulfonyl, N-(4-methyl ring Aminesulfonyl group substituted with a cyclohexyl group having a substituent such as hexylsulfonyl group, N-(4-butylcyclohexyl)amine sulfonyl group; N-phenylamine sulfonyl group, N_(1_benzene) Alkyl sulfonyl, n-(2-phenylethyl)amine fluorenyl, N-(3-phenylpropyl)amine sulfonyl, N-(4-phenylbutyl)amine , N-[2-(2-naphthyl)ethyl]amine sulfonyl, N-[2-(4-methyl 149310.doc 201111447 phenyl)ethyl]amine sulfonyl, N-(3 An arylsulfonyl group substituted with an aralkyl group such as a phenyl-1-propyl group, an aminesulfonyl group or an N-(3-phenyl-1-methylpropyl)amine sulfonyl group. In terms of having a tendency to have high heat resistance, at least one of Ral to RalS is preferably a nitro group. R and R are preferably a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, a cyclohexyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, · Ra32_〇Ra33, _Ra32_c〇〇Ra33 and -Ra32-0. -CO-R_a33 0 In the compound represented by the formula (3), a preferred example of the ratio of the ° azo compound, a compound or the like: as a ligand which becomes a wrong anion, a formula (Ι-al)~ (i_a56) shown 1493l0.doc •41 - 201111447

(1-a5) (1-a7)

(1-a2) (1-a4) (1-a6) (1-a8)

(1-a10) (1-a12)

(1-a14)

(1-a16)

(1-a18) (1-a20) 149310.doc •42 201111447

H2N02S

(1-a23) (1-a25)

02N

〇H HO

Ch3 n=n~〇. (1-a26) so2nh2 02N z OH HO

(1-327) v^N〇2 (1_a29) 〇H HO

(1-a28) (1-a30)

(1-a33)

(1a-32) (1-a34) O2N N=/ /=yCH3 r^VNV~N=N-A ^ (1.a35&gt;

〇H HO Ηί\ν^Ν=

(1-a36) ^ in H〇r'Ning 2

N=N-&lt;\,/&gt; (1-a38) SO2NH2 149310.doc -43- (1-a42) (I^a44) (1-a46) (1&gt;a48) (1-a50) (1 -a52) 201111447

149310.doc 201111447

-Θ

149310.doc -46 -

(1-b20) 201111447

Θ

H〇3s

(1-b28)

149310.doc -47- 201111447

Θ

Cl ch2ch3 (1-b31) Θ .Cr-^ h3ch2c JLT~\ (1-632) ho3s so3h (14)33) Θ Η#. #

Θ (1-b34) σ N〇2

Hozs cr xr

SO3H o X) (1‘W5) o2n so3h e

Θ (1 VII 36) N〇2 .cr

Ό H〇2 Θ H03S'

O2n (1-b37) (1-639)

Θ (1-b3e) Θ (1-b40) 149310.doc -48- 201111447

child. As the compound having a p-Hawthorn skeleton, a monovalent cation derived from a compound having a ruthenium skeleton or a monovalent cation derived from a compound having an anthracene skeleton can be exemplified by the formula (丨), wherein the brightness of the obtained color filter is obtained. In a higher aspect, it is preferably a monovalent cation of 149310.doc-49·201111447 derived from a compound having a P-Hawthorn skeleton. As a compound of the formula (3) Qiu-a _ The compound in the organic solvent is a compound represented by the formula (3-1):

[In the formula (3-1), 'Ra4! to Ra58 independently of each other represent a hydrogen atom, a halogen atom, a monovalent aliphatic hydrocarbon group having an inverse number of 1 to 8, a nitro group, a sulfonic acid group or _s〇2NHRa34; a nitrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, a cyclohexyl group which may be substituted with a group having a carbon number of 14 or 4, _Ra32_〇Ra33, _Ra32 c〇〇Ra33, -Ra32=DC〇-R... or carbon a number of 7 to 1 argon;

Ra32 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; R represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; R and Ra6° independently represent a hydrogen atom, a methyl group, an ethyl group or an amine group; Cr or Co; R independently of each other represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 1 carbon atoms, which is contained in the aliphatic hydrocarbon group and the aromatic hydrocarbon group. The hydrogen atom may be substituted by a base, a sulfonate group, a sulfonic acid group, _S〇3Na, -S〇3K or a halogen atom;

Ra25 and Ra26 respectively represent a ruthenium atom or a methyl group; 149310.doc •50- 201111447

Ra27 represents ethyl, propane-U-diyl or propane·丨, 2•diyl;

Ra28 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; n represents an integer of 1 to 4. In the case of an integer of 2 or more, a plurality of R27s may be the same or different from each other]. Examples of the monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms include the same groups as those of the above Ral to Ra丨8. Examples of the divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms include the same groups as those of the above Ra32. Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a second butyl group, and a third butyl group. Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms include a phenyl group, a methylphenyl group, a dinonylphenyl group, a trimethylphenyl group, an ethylphenyl group, a propylphenyl group, and a butylphenyl group. An aryl group such as a naphthyl group; an aryl group such as a benzyl group, a diphenylmethyl group, a phenylethyl group or a 3-n-propyl group; The cyclohexyl group which may be substituted with an alkyl group having a carbon number of 44 may be exemplified by 2-methylhexyl group, 2-ethylcyclohexyl group, propylcyclohexyl group, 2-isopropylcyclohexyl group, 2-butyl group. Cyclohexyl, 4·methylcyclohexyl, erythrocyclohexyl, propylcyclohexyl, 4-isopropylcyclohexyl, 4-butylcyclohexyl, and the like. In terms of the tendency to have a higher heat resistance, it is preferred that at least one of 匕Ra58 is a nitro group. Also, it is preferably at least one of the RRa45! At least one of Ra46 to Ra5 is a sulfonic acid group or -S〇2NHRa34, more preferably _s〇2NHRa34. Wherein R is preferably a hydrogen atom or a valent aliphatic hydrocarbon group having a carbon number of 丨8, more preferably a hydrogen atom or a 2-ethylhexyl group. In the case of having a plurality of _S02NHRa34 ^ J49310.doc -51 · 201111447 These may be the same or different. In terms of the improvement of the color density, it is preferable that the R gas Ra24' = the carbon number of the substituent - the aliphatic hydrocarbon group, more preferably an air mat or an ethyl group.

The R a27 group is preferably an ethylidene group and a propane group, and a 2-diyl group, more preferably a stretching group B, and a hydrogen atom. η is an integer of from 1 to 4, and is preferably an integer of from 2 to 4, more preferably (8), still more preferably 3. As -(R 〇)nRa28, 2-(2-hydroxyethoxy)ethyl and 2-[2_(2-hydroxyethoxy)ethyl are preferred in terms of solubility in an organic solvent. Oxy]ethyl, more preferably 2_[2_(2-hydroxyethoxy)ethoxy]ethyl. Among the compounds represented by the formula (3-1), examples of the cation derived from the P-salt compound include a cation represented by the formula (1-cl) to the formula (1_C48): • 149310.doc 52 - 201111447 Ten

(1ό1)

149310.doc -53- 201111447

149310.doc -54- 201111447 ©

(1-C25)

(1-C26)

§

(1-C28)

149310.doc -55- 201111447

(1-c41) (1-C42)

O

0

(1-C43)

o

(1-C44)

O

(1-C45)

O

- N

(1-C46)

0 (1-C47), 0,

0

(1^048) Specific examples of the compound represented by the formula (3-1) include a compound represented by the formula (1-1) to the formula (1 20): 56-149310.doc 201111447 H2N〇2S H2N〇2S H2N〇2S h2no2s ho3s o

149310.doc -57- 201111447

H2N02S

N

N-f &gt;-N〇2 Θ

, N - cr

0 (1-6)

So2nh‘ h2no2s

(1-7) (1-8) Θ

L/&gt;_N

.N H2NOzS hr-

So2nh2

, 0 (1-9) 丨 h2no2s N-

Cl Θ cr one or

Cl

N-^ J o

S02NH2 •a

O

(1-10)

, OH 149310.doc -58- 201111447

N^\ , n02

H2N02S* \ Cr Cl P〆 \ so2nh2o

Cl

H2no2s

So2nh2

O2n N_&lt;/1 one

丨〆, /OH Θ

丨^^OH (1-12) h2no2s ,ja

t /&gt;_N

N〇2 Θ X〇- o2n

Λ Xi so2nh2

,N

(1-13) OH

^ N

- o N〇2 Θ cr zCo one o2n

N ^'1 so2nh2

(1-14)

X/OH h2no2s

Λ XX o2n

Θ so2nh2

149310.doc -59- 201111447

(1-16) cr

(1-17)

(1-18) ο

In a specific example of the compound represented by the formula (3-1), the solubility in an organic solvent is preferably a formula (1-1) or a formula (1-3) to a formula (1-5). ), 149310.doc • 60· 201111447 () 弋 (1 9), formula (1-11) ~ formula (1-16) and formula (1-18) ~ formula (1-20) &quot;&quot More preferably, it is a compound represented by the formula (1_1) and a compound represented by the formula (1-3). When the compound represented by the formula (3) is produced, a compound represented by the formula (10) and a complex compound may be used to form a chromium salt, or a compound represented by the formula (3d) may be used to form a starting salt. Thereafter, the salt of the wrong salt pan is subjected to a salt exchange reaction as needed, thereby producing a compound represented by the formula (3).

(3d) [meaning in the formula (3d)].

Ral1 to Ral4 and r al4 al9 are not the same as those in the formula (3). 屯, 屯 屯 屯 孰 孰 孰 孰 孰 孰 孰 孰 孰 孰 孰 孰 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 吡 。 。 。 。 。 。 。 。 。 。 。 The compound of the formula (IV) can be produced by subjecting a star compound to a salt exchange reaction: B, (b)

[In the formula (b), pi a28 R and η are not related to the formula (3_ represents U 贾 anion). The same meaning; A· 149310.doc -61 - 201111447 As the monovalent anion, Cl·, ΒΓ, Γ, C104-, PF6_ or BF4·, etc. The hydrazine compound represented by the formula (b) can be reacted with a compound represented by the formula (b〇) and a compound of the formula (b1) in an organic solvent. And manufacturing:

A Θ [In the formula (bo) and the formula (bl), the ruler...~^ and n have the same meanings as those in the formula, and Α denotes the same meaning as in the formula (b)]. In the reaction, the reaction temperature is preferably 丨5. 〇~6〇. Preferably, the reaction time is preferably from 1 hour to 12 hours. Further, in terms of shortening the reaction time or increasing the yield, it is preferred to use an acid catalyst and/or a dehydrating agent. Examples of the acid catalyst include sulfuric acid and p-toluenesulfonic acid. *As a dehydrating agent', it may be exemplified by dicyclohexylcarbodiimide, diisopropylsuccinimide, hethyl_3_(3-dimethylaminopropyl)carbodiimide hydrochloride a carbodiimide such as a salt; a K alkyl-2-halopyridinium salt; a carbonyl group of a bis(2-oxooxazolidinyl)phosphinium chloride; More than salt). Among them, as a dehydrating agent, it is easy to carry out post-treatment. In terms of purification, h-ethyl-di-decylaminopropyl) succinimide hydrochloride is preferred. The organic solvent to be used for the above-mentioned anti-accumulation may be, for example, dichloromethane, chloroform, tetrahydrofuran, toluene or acetonitrile. 149310.doc • 62· 201111447 The compound represented by the formula (3 -1) is produced by dissolving the above-mentioned salt in the solvent m with the wrong salt and the salt of the formula (b). Preferably, the compound (8) is reacted in a molar ratio of 1] to 1 molar. It is a pigment which can be an organic pigment and an organic pigment. ^ For: Jiawei As an organic pigment, you 丨 &amp; /± m bulletin, etc.: Patent Special Opening 2°03·327864 Material Blue 15'153 5 kinds of organic pigments. "'It is preferably blue pigments such as Ο. Yan·4, 15:6, 60; CL pigment purpura, 36, 38 special purple pigment; CI pigment green 7, 5 25, 36, 47 and 58 green pigments; CI Pigment Yellow i, 3, 12, 13 'Μ, 15, 16, 17, 2, 24, 3, 53, μ, %, 94 1〇9, 110, 117, 125, 128, Π 7, 138 ' 139 'M8 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; C.1. pigments such as muun, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; C·!. 9, 97, 1〇5, 122, 123, 144, 149, 166, 168, H 177, (10), 192, (4), 215 216 224 242, 254 '255, 264, 265 and other red pigments, etc. In the case of producing a colored calender, the colored composition is prepared as a blue composition, a green composition and a red composition. The blue composition preferably contains a pigment selected from the group consisting of CI pigment red violet 23, c Blue 15:3, CU. Pigment Blue 15:6 to a pigment, more preferably contains [丄 Pigment Blue 15:6. The green composition preferably contains a color selected from CI. Pigment Green%, CI·Pig Green 58 , CI Pigment Yellow 138, CI·Pigment Yellow 150 At least i 1493I0.doc -63- 201111447: The composition preferably contains at least one selected from the group consisting of: pigment yellow i38, d pigment &quot; heart. Pigment yellow 15G, CL pigment red heart cm. Pigment red 242, 丄 Pigment red 254! These pigments may be used singly or in combination of two or more. Pigments, especially organic pigments, may also be subjected to rosin treatment, use of a pigment derivative containing an acidic group or an experimental group, and the like. The graft treatment of the surface of the pigment by a π knife compound or the like, the washing treatment using an organic solvent or water for removing impurities, the removal treatment for removing ionic impurities by an ion exchange method, etc. The pigment is preferably uniform. In the method for producing the pigment dispersion liquid of the present invention, the pigment to be used is finer than the pigment to be subjected to the refining treatment. Examples of the refining treatment include salt milling treatment, sulfuric acid micronization treatment, etc., preferably salt milling treatment. The so-called salt-grinding treatment refers to the process of heating (a mixture of water-soluble inorganic salts and water-soluble organic solvents) using a kneader, a double-light grinder, The three-roll mill, ball mill, grinder, sand mill and other kneading machines are mechanically kneaded. Then the water-soluble inorganic step and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt system serves as a crushing aid. The role of the agent. In salt milling, the pigment is pulverized by the high hardness of the inorganic salt. Since the pulverization of the pigment occurs simultaneously with the crystal growth in the active surface due to pulverization, if the mixing conditions are different, the pigment obtained The primary particle size is different. The kneading temperature is preferably 4 〇 15 15 (rc.) If the kneading temperature is within the above range, the crystal growth during the kneading process can be promoted, and the shape of the obtained pigment particles is 149310.doc -64 - 201111447. When the heating temperature is less than 4 °C, the helmet method fully crystallizes and the length of the pigment particles is close to amorphous, and in other respects, the heating temperature exceeds 丨. In the case of 5 〇 °c, the primary particle size of the pigment becomes large, so it is not good as a color 遽 ° ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ ～ In terms of cost, the mixing time of the salt milling treatment is preferably 2 to 24 hours. By optimizing the conditions for salt grinding treatment of the pigment, the secondary particle diameter is very fine, and the range of the distribution is narrow and dense. a pigment having a t-degree distribution. The color of the color-developing sheet obtained by using the color-developing composition containing such a pigment is excellent. As a water-soluble inorganic salt used for the salt-milling treatment, a gasification nano, a chlorine, a lock, or the like can be used. Chlorine A lacks sodium sulfate, etc., on the price side Μ, is preferably used: sodium salts U). In terms of both treatment efficiency and production efficiency, the total amount of the soluble inorganic salt relative to _ is preferably ❹5 core 2%, and the best use is 3004,00 (quantity %. The pigment and the water-soluble I machine are not particularly limited as long as they are soluble (mixed) in water and inorganic salts, and are preferred in terms of evaporation and safety in salt grinding. Further, it is preferably a boiling point of 120. (: The above! For example, 2: methoxyethanol, 2·butoxyethanol, 2 like oxy) ethanol, 2-(hexyloxy)ethanol can be used. , diethylene glycol, a j ether, diethylene glycol monobutyl ether, triethylene glycol, tri-alcohol, early polyethylene glycol, liquid milk based ~ 2 - propanol, dipropylene two 149,310. Doc •65- 201111447 .... Monomethyl ether, dipropylene glycol, monoethylidene (iv) liquid polypropylene glycol, the total amount of organic solvent relative to the pigment is preferably 5~1, 〇〇〇 mass%, More preferably, it is used in an amount of 5 〇 to mass %. Species:::: When processing, it is necessary to add a resin as needed. The resin used is not particularly limited. The natural resin, the modified natural resin, the synthetic resin such as the New Moon, and the synthetic resin modified by the natural resin are preferably used in the official and the inch. The partially soluble body is insoluble or insoluble in water, and More preferably, the total amount is preferably 52: γ agent. The amount of the resin used (4) is preferably in the range of 5 to 200% by mass. In the method for producing a pigment dispersion of the present invention, dispersibility, and improvement of the pigment The agent is classified as "the agent. It is preferable to use a pigment dispersion 乍 as the pigment dispersant, and a surfactant such as a nonionic, amphoteric ion, an anthraquinone or an anion. H $ η I糸, polyamine system, and acrylic type are used in two ways: 4 pigment dispersant can be used alone or in combination with a dispersing agent. The amount of (4) is better than the mass per mass: mass: 2 When the amount is in this range, the tendency of the dispersion of the pigment dispersant is stored. Only the pigment in the uniform dispersion state is dispersed in the Yankee dispersion of the present invention, and the dispersion stability of the pigment is improved. Pigment derivatives (here with dyes) Not J, etc.:: used as a dispersion aid: azo system, system, two organisms, heart system, Benzimidazolone, i49310.doc • 66 · 201111447 Quinone, isoindolinone Department, isoporphyrin system, twenty well system, lanthanum indanthrene system, lanthanide, perinone system, diketone η than 嘻幷 各 各 各 各 各Derivatives. Pigment derivatives are generally poorly soluble in organic baths. As a substituent of the pigment derivative, a sulfonic acid group, a fe% fluorenyl group and a quaternary salt thereof, an phthalimide methyl group, N, N-dialkylamino group &amp; base, via group, county, amine mercapto group or the like directly or via an alkyl group, an aryl group, a heterocyclic group or the like bonded to the base of the pigment skeleton, preferably amine % The sulfhydryl group and its quaternary salt, sulfonic acid group, more preferably a sulfonic acid group. Further, the substituents may be substituted for a plurality of pigment skeletons or a mixture of different algebraic compounds. Specific examples of the pigment derivative include a sulfonic acid derivative of an azo pigment, a sulfonic acid derivative of a phthalocyanine pigment, a sulfonic acid derivative of a quinophthalone pigment, and a sulfonic acid derivative of an isoindoline pigment. A sulfonic acid derivative of an anthraquinone pigment, a sulfonic acid derivative of a quinacridone pigment, a diketone ratio, a rhodium derivative of each pigment, a derivative of a second acid, a continuous acid derivative, and the like. In the method for producing a pigment dispersion of the present invention, a part or all of the resin selected from the group consisting of the following resins (B) may be contained. Specifically, in the dispersion treatment step in the case where the pigment dispersion liquid is prepared as follows, the binder resin is contained together with the above-mentioned pigment dispersant, and the binder resin can contribute to dispersion stability by synergistic effect with the dispersant. Preferably. In the local Mingzhong, it is preferable to contain the dye and the pigment in the mass ratio of the dye: pigment=1:99 to 99:1, preferably 1:99~6〇:4〇, and more preferably 5:95~ 40:60. By setting the above ratio, it is easy to optimize the transmission spectrum, and it is possible to obtain a color pattern having high contrast and high brightness, and further, the heat resistance and chemical resistance of the obtained color pattern of 1493l0.doc.67-201111447 are improved. In the case of the blue composition, it is preferred that the ratio of the pigment "隹" is &quot;··]~40:6〇, more preferably 97:3~5〇.5〇, and further preferably as 70:30 β in the color combination. When it is shaped, the private society* view, and the feeling of the distribution..., from C·1·Pigment Green 36, CI Pigment Green 58, c 138 and C 丄 Pigment Green 150 To 丄 枓 枓 99·ΐ.4Π., η, the mass ratio of at least 1 to the dye is • 6〇, more preferably 99:1~50:50, and further #A 鍫人, When 95,5~55:45, and σ is a red composition, it is preferably selected from the group consisting of CI yan, bismuth pigment yellow 150, C.1. · Pigment red 177, CI 颜 η η ί ^ 'L·1·Neck blush 242 and CI Pigment Red 254 at least 1 99-1 40, η diameter, *枓 mass ratio is .1~4〇:6 〇, more preferably 99:1 to 50:50' and still more preferably 97 3 to 65. 35: In the method for producing a pigment dispersion of the present invention, the above-mentioned dye virtual pigment is simultaneously dispersed in a solvent. The solvent used in the invention includes the following. For example, the solvent used in the present invention. In the evening, an alcohol such as an alcohol or a polyhydric alcohol is used as the alcohol, and examples thereof include decyl alcohol, ethylene glycol, propanol, butanol, pentanol, hexanol, cyclohexanol ethylene glycol, propylene glycol, and internal triol. Further, a glycol ether such as ethylene glycol or propylene glycol may be mentioned. Examples include ethylene glycol monomethyl sulphate, ethylene glycol mono(10), ethylene glycol monopropyl sulphate, ethylene glycol monoisopropyl ether, and Ethylene glycol monoalkyl ether such as diol monobutyl bond; propylene glycol monoalkyl ether such as alcohol monopropyl ether, propylene glycol propylene glycol monodecane, propylene glycol monoethyl ether or propylene dibutyl ether; 149310.doc -68 - 201111447

a propane ether such as propylene glycol dioxime ether, propylene glycol diethyl ether, propylene glycol ethyl methyl ether dipropylene ether, propylene glycol propyl ether ether or propylene glycol ethyl propyl ether; dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol hydrazine Dipropylene glycol dialkyl ethers such as diethyl ether; dipropylene glycol monoalkyl ethers such as dipropylene glycol monomethyl ether and dipropylene glycol monopropyl ether; 3 - mercaptobutanol, butylbutanol, propoxybutanol , butoxybutanol _ and other butanediol monoalkyl ethers; diethylene glycol dioxime ether. Ethyl ethers including acetaminophens and phthalocyanates may be mentioned. Ethylene glycolate, ethyl celecoxib acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monoethyl ether acetate, etc. Propylene glycol, such as acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl acetate, acetic acid esters; propylene glycol oxime ether propionate, propylene glycol diethyl ether propionate, propylene glycol propyl ether propionate, propylene glycol butyl ether Propylene glycol alkyl ether propionate such as propionate; decyloxybutyl acetate, ethoxybutyl acetate, propoxy butyl acetate, butoxybutyl acetate, etc. Glycol monoalkyl ether acetate; butylene glycol monobutyl ester, ethoxybutyl propionate, propoxy butyl acrylate vinegar, butoxy butyl propionate and other butanediol single Alkyl ether propionates; diethylene glycol monoalkyl ether acetates such as diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate; dipropylene glycol monomethyl ether acetate, etc. Dipropylene glycol monoalkyl ether acetate; 1493IO.doc -69- 201111447 propanol monoethyl ether acetate; decyl pentyl acetate vinegar and the like. Diphenylene and mesitylene As the aromatic hydrocarbons, benzene, benzene, and the like are mentioned. Examples of the hydrocarbons include cyclohexans and the like. Examples of the ketone include methyl ethyl ketone, acetone, methyl amyl, decyl isobutyl ketone, cyclohexanone, N_f pyrrolidone, and 4-hydroxy-4-indolyl 2 pentyl嗣, 2_butanone, 2'-heptanone, 3-heptanone, 4-heptanone, 4-mercapto-2-pentane, cyclopentanone, cyclohexanone, isophorone, and the like. Examples of the esters include methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, 2-hydroxy-2-indole propionate, and 2-hydroxy-2-methyl. Ethyl propyl propionate, methyl hydroxyacetate, ethyl hydroxyacetate, butyl glycolate, methyl lactate, ethyl lactate, propyl lactate, butyl lactic acid, 2-mercapto lactate, 3 hydroxypropionic acid Methyl ester, 3-hydroxypropionic acid ethyl, 3-hydroxypropyl propionate, butyl 3-hydroxypropionate, 2-hydroxy-3-indolyl decanoate, decyloxyacetate, decyloxy Ethyl acetate, propyl oxyacetate, butyl methoxyacetate, decyl ethoxyacetate, ethyl ethoxyacetate, propyl ethoxyacetate, butyl ethoxyacetate, propoxyacetic acid Ethyl ester, ethyl propoxyacetate, propyl propoxyacetate, butyl propoxyacetate, methyl butoxyacetate, ethyl butoxyacetate, propyl butoxyacetate, butoxyacetate Ester, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, butyl 2-methoxypropionate, decyl ethoxy propionate, Ethyl 2-ethoxypropionate, 2- Propyl oxypropionate, butyl 2-ethoxypropionate, decyl 2-butoxypropionate, ethyl 2-butoxypropionate, 149310.doc -70- 201111447 2-butoxypropionic acid Propyl ester, butyl 2-butoxypropionate, decyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, 3-methoxypropionic acid Butyl ester, decyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, propyl 3-ethoxypropionate, butyl 3-ethoxypropionate, 3-propoxypropionic acid Ethyl ester, 3-propoxypropionic acid B, Z-propoxy propionate, 3-propoxypropionic acid, methyl 3-butoxypropionate, 3-butoxy Ethyl propionate, propyl 3-butoxypropionate, butyl 3-butoxypropionate, ethyl pyruvate, and the like. Examples of the cyclic ethers include tetrahydrofuran, pyran, tetrahydropyran and the like. Examples of the cyclic esters include γ-butyrolactone and the like. Examples of the guanamines include hydrazine, hydrazine, hydrazine, hydrazine, hydrazine, hydrazine, hydrazine, hydrazine, hydrazine, hydrazine, and the like. The solvent used in the dispersing step is preferably an ether acetate vinegar, an acid brewing cockroach, more preferably an ether acetate vinegar, and more preferably a propylene glycol early acetal acid. If these solvents are present, the surface of the obtained color light-passing sheet tends to be less likely to generate foreign matter. /The equal coolant can be used alone or in combination of two or more. Also, there may be a plurality of solvents. The pigment dispersion of the present invention is uniformly dispersed in the powder and dried in the dyed d. At the same time, it does not refer to the time of the instant, but refers to the evaluation of μ, +. W. In the same solvent in the 'Bian> glutinous rice in the solution, the heat and cooling of the distant cancer enamel are not carried out, and the second: ^ is also continued to be the minimum order. 4 Other operations or restrictions «Arbitrary Force 2: == In the same solvent, stir, etc. and evenly divide it into 149310.doc •71- 201111447 scatter/, put the two into the same solvent and disperse in one step. The method of dispersing the dye and the pigment at the same time is not particularly limited, and it can be carried out by a known apparatus, a known method, or the like. The dispersing agent and the solvent may be dispersed in a solvent, or the dye or pigment may be dissolved in a solvent and then mixed and dispersed. The dispersion is preferably carried out using a paint shaker, a sand mill, a y calendar machine (sand coffee), a ball mill, a pro-mill, a stone mill, a jet mill, a homogenizer or the like. By dispersing as described above, the pigment can be microparticulated, so that the coating of the colored composition: +:, 'The color filter obtained from the colored composition has a higher contrast. When the material is shaken and dispersed (4), it is preferred to use a glass bead or an oxidized material having a diameter of _. The temperature at which the dispersion is carried out is preferably 100 C or more, and more preferably 2 G to 8 (the time at which rc or more is 4 as the time of dispersion is 1 to 20 hours), preferably 1 to about 20 minutes, depending on the composition of the pigment dispersion liquid. The method for producing the coloring composition of the present invention is exemplified by the pigment dispersion liquid (4), and the mixture is selected from the group consisting of a solvent (8), a resin (B), a photopolymerizable compound (C), and light. Method 0 of selecting at least one of the group consisting of the polymerization initiator (D) The solvent may be used as it is, and may be used as it is, or may be mixed as appropriate. Further, the color combination is produced. The total amount of the dye and the pigment is 149310.doc • 72· 201111447. The solid content in the coloring composition is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, and even more preferably 1%. ～50质量百分比。 Here, the solid content component refers to the total of the components other than the solvent in the coloring composition. If the content of the dye and the pigment is within the range @, the color of the resulting colored pattern or color filter is obtained. Full density and available in groups The resin (B) is not particularly limited as long as it contains a necessary amount of a binder polymer, and a coloring pattern or a color light-receiving sheet having excellent mechanical strength is formed. For example, an alkali-soluble resin is preferably contained. It is not particularly limited, and any resin can be used. For example, the alkali-soluble resin contains a structural unit derived from (meth)acrylic acid. Here, (mercapto)acrylic acid means acrylic acid and/or methacrylic acid. The content of the acrylic acid-derived structural unit is preferably 16 mol% or more, 4 mol% or less, more preferably 18 mol% or more, and 38 mol% or less, based on all structural units constituting the alkali-soluble resin. When the content of the structural unit derived from methyl)acrylic acid is within the above range, the solubility in the non-pixel portion during development is improved, and the non-pixel portion after development is less likely to remain in the residue. Examples of the other monomer constituting the structural unit other than the structural unit derived from (meth)acrylic acid of the alkali-soluble resin include an aromatic vinyl compound and an unsaturated group. Acid esters, aminoalkyl esters of unsaturated carboxylic acids, glycidyl esters of unsaturated carboxylic acids, vinyl carboxylates, unsaturated ethers, acrylonitrile compounds, unsaturated amides, unsaturated quinones a class of aliphatic conjugated dienes having a monoacrylonitrile group at the end of the polymer molecular chain or a single 149310.doc

C 201111447 Macromonomers of mercapto acrylonitrile groups, units represented by formula (π) and units represented by formula (III):

(In the formulae (II) and (III), 'R80 and R82 each independently represent a hydrogen atom or a methyl group. R and R each independently represent a wind atom or a carbon group having 1 to 6 carbon atoms). As the alkali-soluble resin, specifically, a methacrylic acid / benzyl methacrylate copolymer, a methacrylic acid / benzyl methacrylate / styrene copolymer, a methacrylic acid / benzyl methacrylate / Isofuran methacrylate copolymer, methyl acrylate/phenethyl hydrazine/methacrylic acid vinegar/N-phenyl maleimide copolymer, thioglycol/formula (II) a constituent (wherein in the formula (II), 'R53 represents a fluorenyl group, R54 represents a hydrogen atom) / methyl = a benzyl olefin copolymer, and a structural unit represented by the formula (II) (wherein, In II), R53 represents a methyl group, and R54 represents a hydrogen atom, which is a benzyl ester of butyl ruthenium acrylate, and a structural unit represented by the formula (III) (wherein the household j (III) In the formula, R55 represents a fluorenyl group, and R56 represents a hydrogen atom sulfonate-based tricyclodecyl acrylate copolymer, etc. Especially in terms of hardenability and developability, an alkali-soluble resin: 卞八本ethylene copolymer/甲比佳佳式(IV) shown 149310.doc • 74· 201111447

A resin, for example, a benzyl mercaptopropionate copolymer, can be obtained by combining two components to form a structural unit of the formula (II) and a structural unit represented by the formula (II) / methyl propyl group The compound reactant of the thiol acrylate and the thiol acrylate is condensed, and then the obtained 2-component polymer is obtained by the formula (v). Mercaptopropionic acid / 4 μ μ 〇 heart, as shown in formula (III), ,, mouth structure, early / stupid ethylene copolymer / tricyclodecyl methacrylate copolymer can be transferred by Mokko A benzyl acrylate, a methyl acrylate acid, a tricyclic fluorene skeleton, a monomethyl methacrylate copolymer and a compound represented by the formula (VI) are obtained by reacting:

(VI) [In the formula (V) and the formula (VI), and R83 represents the same meaning as described above. The copolymerization is usually carried out by using a polymerization initiator in a solvent. : Nitrogen:: Starter' can be used, for example, 2,2'-azobisisobutytin: nitrogen or (2-methylpropionic acid methyl vinegar) or the like W醯 or peroxylated tert-butyl Classes of peroxides, etc. 149310.doc •75· 201111447 Solvents can be dissolved as long as they can be used, for example: one &amp; C*, per monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monoterpene ether A glycol ether ester such as an acid ester or propylene glycol monoethyl ether acetate, or the like. g The reaction temperature may take into consideration the decomposition temperature of the polymerization initiator, and the solvent. . The boiling point of the body is determined. Further, the side chain of the copolymer obtained in the above manner may be modified by a compound having a polymerizable group to prepare a photosensitive alkali-soluble resin. At 1 o'clock, a catalyst for introducing a polymerizable group into the resin may be added. Examples of the catalyst include tris-dimethylaminomethylphenol and the like. Further, an additive for preventing side reactions may be added. As the additive, for example, hydroquinone or the like can be mentioned. As the alkali-soluble resin, for example, the following copolymers and the like can be exemplified. [K1] an unsaturated carboxylic acid and/or an unsaturated carboxylic anhydride (B1) (hereinafter sometimes abbreviated as "(m)"), and a monomer (B2) having a cyclic ether structure having a carbon number of 2 to 4 (below) Sometimes referred to as "(B2)") polymerized copolymer. [K2] A copolymer obtained by polymerizing (B1), (B2) and a monomer (B3). Here, the monomer (B3) (hereinafter sometimes abbreviated as "(B3)") is a monomer which can be copolymerized with (B1) and/or (B2) and is different from (B1) and (B2). [K3] copolymerization obtained by reacting a part of a carboxyl group derived from (B1) in a copolymer of (B1) and (B3) with a cyclic ether structure derived from a carbon number of 2 to 4 of (B2) Things. [K4] a copolymer of (B1) and (B3). Preferred is a copolymer obtained by polymerizing at least (B1) and (B2). 149310.doc • 76· 201111447 As (Bl), for example, an aliphatic unsaturated carboxylic acid and/or an aliphatic unsaturated slow anhydride can be mentioned. Specific examples thereof include unsaturated monocarboxylic acids such as propylene I, mercaptoacrylic acid, and crotonic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, and itaconic acid. ; and methyl-5-norfosin 2,3-di-hypo-acid, 5-hydroxybicyclo[221]hept-2-di, 5,6-monocarboxybicyclo[2.21]hept-2-ene, 5 Carboxyl-5(indenyl)bicyclo[2 2 J]hept-2-ene, 5·carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbis% [2.2 _1]g-_2, dilute, 5-remediate_6-ethylbicyclo[2·21]hept-2-ene and other bicyclic unsaturated compounds containing a slow group; maleic anhydride, citraconic anhydride, clothing Acetic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydroortho Phthalic anhydride, dimethyltetrahydrophthalic anhydride 5,6-monocarboxybicyclo[2·2·1]hept-2-ene anhydride (himic acid anhydride), etc. Saturated dicarboxylic acid anhydride; succinic acid mono [2-(methyl) propylene methoxyethyl] ester, phthalic acid mono [2-(methyl) propylene methoxyethyl] ester, etc. Polycarboxylic acid Unsaturated mono[(meth)acryloxyalkyl]ester; unsaturated acrylate having a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid. Among them, acrylic acid, methacrylic acid or maleic anhydride is preferable in terms of copolymerization reactivity and alkali solubility. These may be used alone or in combination of two or more. In addition, in the present specification, the compound, the component, and the exemplified compound, etc., which are exemplified, may be used singly or in combination of two or more. In the present specification, "(meth)acrylic acid" means one selected from the group consisting of acrylic acid and methacrylic acid. "(Methyl) propyl sulfhydryl" and "(methyl) and g 酷 酷 A* *, 丞) internal olefin 鲛 ^ J also have the same meaning. (B2) as long as it has a carbon number selected from At least one of the groups consisting of a ring-shaped structure of 2 to 4 (for example, an epoxy oxime structure, an oxetane structure, and a tetrahydroanthracene structure) can be "and preferably has an unsaturated state" The (B2) may, for example, be a monomer having an oxirane group, a monomer having an oxaethyl group, a tetrahydrofuran group, or the like. The term "body" means a polymerizable compound having at least an anthracene group selected from the group consisting of, for example, an aliphatic epoxy group and an alicyclic epoxy group. The monomer having an epoxy group preferably has an olefin selected from the group consisting of At least one of the group consisting of the epoxidized structure and the structure in which the cyclic olefin is epoxidized, and the compound having an unsaturated bond are more preferably selected from the group consisting of a structure obtained by epoxidizing an olefin and At least one of a group consisting of a structure in which a cycloolefin is epoxidized, and (methyl) A monomer having a structure in which an olefin is epoxidized, and specific examples thereof include glycidyl (meth) acrylate, β-t-glycidyl (meth) acrylate, and (methyl). A compound represented by the following formula (VI), which is described in JP-A-H07-248625, which is described in Japanese Patent Application Laid-Open No. Hei 7-248625, and the like: 1493l0.doc -78 - 201111447 R86 ml (VI) (In the formula (VI), R84 to R86 are each independently a hydrogen atom or a carbon atom having 1 to 10 carbon atoms, and ml is an integer of 1 to 5.) The compound represented by the above formula (VI) is, for example, It can be exemplified by o-ethene-glycidyl glycidyl ether, m-vinylbenzyl glycidyl ether, ethylene-glycidyl glycidyl ether, α-mercapto-o-ethylidene glycidyl hydrazine, α-methyl-m-ethylene Benzyl glycidyl ether, α-mercapto-p-ethylene benzyl glycidyl hydrazine, 2 3 diglycidyloxy fluorenyl stupid ethylene, 2,4-diglycidoxymethyl styrene, 2,5 - diglycidoxymethylstyrene, 2,6-diglycidoxymethylstyrene, 2,3,4-triglycidoxy Styrene, 2 3 5_triglycidyloxydecyl styrene, 2,3,6-triglycidyloxymercaptostyrene, 3,4,5-triglycidoxymethylstyrene, 2 4, diglycidyloxymethyl styrene, etc. As a monomer having a structure in which a cycloolefin is epoxidized, a monomer having a structure in which a monocyclic ring-making hydrocarbon is epoxidized is exemplified. a monomer having a structure in which a polycyclic cycloolefin is epoxidized, etc., and a monomer having an ethylene-fired structure preferably has a structure selected from the group consisting of a single ring and a weeping, clothing Qing 垣 虱 及 及 及 及 及 及 及 及 及 及 及 及 及 及 及 及 及 多 多 多 多 多 多 多 多 多 多 多 多 多 多 多 多The compound having a structure and an unsaturated bond is at least selected from the group consisting of a structure in which a single ring of Yanling net w # is more preferably an epoxidized olefin. a monomer of propylene oxime. ,, '. Structure, and as a ring of the above single ring, for example, phantom, pentene, cyclohexane I493I0.doc 79- 201111447 dilute, % heptane, cyclooctene and the like. Among them, a compound having a carbon number of 5 to 7 is preferred. Specific examples of the monomer having a structure in which a monocyclic cycloolefin is epoxidized include ethylene oxide cyclohexanone, 2-epoxy-4-vinylcyclohexan] (for example, Celloxide 2000; Daicel Chemical Industries Co., Ltd.), _3,4_epoxycyclohexyl decyl acrylate (for example, Cycl〇mer A4〇0; Daicel Chemical Industries Co., Ltd. by &quot;k) mercapto acrylic acid _3,4 Epoxycyclohexyl hydrazine (for example, Cyclomer M100 'manufactured by Daicel Chemical Industries Co., Ltd.) and the like. Examples of the polycyclic cycloolefin include dicyclopentene, tricyclodecene, butene, isodecene, bicyclooctene, bicyclononene, bicycloundecene, and dicycloundecene. Bicyclododecene, tricyclododecene, and the like. Among them, a compound having a carbon number of 8 to 12 is preferred. The monomer having a structure obtained by epoxidizing a polycyclic cycloolefin, for example, is selected from the group consisting of acrylonitrile-3,4-epoxynorboxyl ester and methacrylic acid-3,4-epoxynorbornyl ester. a compound represented by the formula (νπ) and at least a compound of the group consisting of the compound represented by the formula (νπι):

In the formulae (VII) and (VIII), the ruler 87 and the ruler 88 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group; X87 and X88 respectively Independently represents a single bond, alkanediyl group of carbon number ι~6 or 149310.doc -80- 201111447 *-(CH2)s-X'-(CH2)t-; X' represents -s~, -O- or - NH-; s represents an integer of 1 to 6, and t represents an integer of 〇~6; wherein s + t$6; * represents a bond with Ο]. Specific examples of R87 and R88' include a hydrogen atom; an alkyl group such as a mercapto group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a t-butyl group, and a t-butyl group; Hydroxyethyl, 2-hydroxyethyl, hydrazine-hydroxypropyl, 2, propylidene, 3-hydroxypropyl, hydrazine-hydroxy-methylethyl, 2-hydroxymethylethyl, 1-hydroxybutyl A hydroxy-substituted alkyl group such as 2-hydroxybutyl, 3-hydroxybutyl or 4-chattybutyl. Among them, a hydrogen atom, a fluorenyl group, a fluorenyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group are preferable. More preferably, it is a hydrogen atom or a sulfhydryl group. Examples of the alkanediyl group having 1 to 6 carbon atoms of X71 and X72 include a methylene group, an ethylidene group, a propane-1,2-diyl group, a propane-1,3-diyl group, and a butane-based group. Pentane-1,5-diyl, hexane-1,6-diyl and the like. Among them, a single bond, an anthracene group, an extended ethyl group, _〇_CH2_, is preferable. More preferably, it is a single bond, -〇-(CH2)2-. 2 at least one compound selected from the group consisting of the compound represented by the formula (VII) and the compound represented by the formula (¥111) is preferably selected from the group consisting of the compound represented by the following formula and the formula (viir). At least one compound of the group consisting of:

(VII·)

(VIIP) 149310.doc • 81 - 201111447 In the formulae (VII,) and (VIII,), R89 and r9〇 have the same meanings as the above-mentioned r87 and r88, respectively. The compound represented by the formula (VII) may, for example, be a compound represented by the formula (vn-丨) to the formula (VII-1 5). Preferred are the formula, the formula (VII 3), the formula (VII-5), the formula (VII-7), the formula (νπ-9), and the formula (νπ_15). More preferably, it is a formula (VII-1), a formula (VII-7), a formula (VII-9), and a formula (VII-15): Ο H2C: CH-c~~o H2C: CH~C-〇-CH2

(VIM) H2C-CH-c-o-c2h4-s —C2H4—R CH3〇 ,,Λ I II H2c=c-C—O—C2H4—s

o HjOCH—C'~~0 〇 (VH-3) o

H2C: CH CH30 HjCeC—Q. 俨3〇 H2C=C-c-o-ch2 CH3o I II h2C=C-c—0—C2H4 CH30 H2Cs=C—C—〇—〇2H4~〇

Ch3o H2〇=C1 C—C2H4—HjC: ch2oh o H2〇=C 0 a o c2h4oh o h2c=c-c— rto

(VII-15) The compound represented by the formula (viii) may, for example, be a compound represented by the formula (vnu) to the formula (乂111-15). Preferably, it is a formula (^111_1), a formula ^111_3), a 149310.doc • 82, 201111447, a formula (VIII-5), a formula (VIII-7), a formula (VIII-9), and a formula (VIII-ll). (VIII-15). More preferably, it is a formula (VIII-1), a formula (VIII-7), a formula (VIII-9), and a formula (VIII-15):

HaC^CH—C-O-C2H4 〇 II H2C:CH—C—Ο—C2H4—0 H2C=C—c-o CH30 f I II HjC^C—C*~O—CHj

(Vffl-7) 0

CH2OH o I II h2c=c-c-o c^h4oh o H2c-i 11

CH30 HjC—C—C—O—C2H4-O (VIII-12) ΪΗ3 π 一Ο—CjHi·

At least one compound selected from the group consisting of the compound represented by the formula (vii) and the compound represented by the formula (VIII) can be used alone. Further, it is also possible to mix at any ratio. In the case of mixing, the mixing ratio is preferably a formula (VII) in a molar ratio: a formula (VIII) of 5:95 to 95:5, more preferably 10:90 to 90:10, and still more preferably 20:80~80:20. As the above monomer having an oxetane group, a compound having an oxetane group and an unsaturated bond is preferred, and more preferably an oxetane group and 149310.doc • 83-201111447 (A A monomer of a propylene oxime group. Ami =, T-based monomer, specifically can be cited: 3 - methyl · 3 · = = methyl oxetane, "based · oxymethyl oxime oxime Ding Xuan, 3-r Its base _3_ f-based propylene oxy-oxyl oxetane, meta-ethyl 3-methoxypropoxymethyl oxetane, 3-methyl-3-methylpropenyloxyethyl Gas mixture π, soil m 杂 rolling % butane, 3 · methyl-3-propenyloxyethyl oxa% &lt; Ding pit, 3_ethyl · 3 · methacryloxy a oxetane or 3-ethyl-3-propenyloxyethyloxetane, etc. As the above-mentioned monomer having a tetrahydrofuranyl group, it is preferred to have a tetrachloroguanidine group and not The compound having a saturated bond is more preferably a monomer having a tetrahydrocarbyl group and a (meth) acryloxy group. Specific examples of the monomer having a tetrahydrofuran group include tetrahydrofurfuryl acrylate (for example, Viscoat V# 150, (manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc. Examples of the copolymerizable monomer (B3) include methyl (meth)acrylate and ethyl (meth)acrylate. (meth)acrylic acid Butyl vinegar, (mercapto) acrylic acid, second butyl vinegar, (mercapto) acrylic acid, third butyl vinegar, etc. (alkyl) acrylates; (mercapto) propylene cyclohexyl ester, (曱Benzyl-2-mercaptocyclohexyl acrylate, (fluorenyl) acrylic acid tricyclo [5.2.1.02'6] oxime-8-yl vinegar (in the technical field, the conventional name is called ( (cyclopentyl methacrylate), dicyclopentyloxyethyl (mercapto) acrylate, isobutyl (meth) acrylate (cycloalkyl) acrylate, phenyl acrylate (methyl)propionic acid benzyl ester or the like (meth)acrylic acid ary 149310.doc -84- 201111447 base ester; diethyl maleate 'diethyl fumarate, itaconic acid II a dicarboxylic acid diester such as ethyl ester; a hydroxyalkyl ester such as 2-hydroxyethyl (meth)acrylate or 2-hydroxypropyl (meth) acrylate; bicyclo [2.2.1] g-2 - alkene, 5-methylbicyclo[2.2.1]hept-2-yl, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[22.^h---ene, 5 -hydroxyindenylbicyclo[2.2.1]hept-2-yl, 5-(2'-ylethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2 .1]g 2 -ene, 5-ethoxybicyclo[2.2.1 ]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di ( Hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2,-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dioxaoxybicyclo [2.2.1] Hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-mercaptobicyclo[2.2.1]hept-2-ene , 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2_1]hept-2-ene, 5·t-butoxycarbonyl Bicyclo[2 2 ^heptyl-ene, 5-cyclohexyloxybicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6 a bicyclic unsaturated compound such as bis(t-butoxycarbonyl)bicyclo[221]hept-2-ene or 5,6-di(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; -Methyl cis-butyl quinone imine, hydrazine-ethyl cis-butyl bis-imine, propyl maleimide, etc. Ν-alkyl maleimide; Ν-cyclopentyl顺-cycloalkyl maleimide, such as maleimide, Ν-cyclohexyl maleimide, fluorene-cyclooctylmethyleneimine, etc.; Ν-adamantyl cis Butene Dimethyleneimine, hydrazine _ 彳 彳 基 基 基 1 1 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 493 Butylene diimine imine, etc. aryl maleimide; N-benzyl maleimide, N-aralkyl maleimide, N-butyl iminoimine Base_3_ maleimide benzoate benzoate, butyl imino 4-pyrene; ^] 醯 16 16 butyric acid vinegar, &amp; dimethyl quinone imine _6 · cis-butene Derivatives of diterpene imine hexanoate, N-butanediamine, 3 - maleimide, propionic acid vinegar, Ν_(Μ 基), maleimide, etc. Benzene, α-methylstyrene, m-decyl styrene, p-methyl styrene ethylene vinyl toluene, p-methoxy acetophenone, acrylonitrile, mercapto acrylonitrile, ethylene, partial gas Ethylene, acrylamide, methacrylamide, ethylene acetate, U·butyl dichloride, isoprene, 2,3 • dimethyl·^-butadiene, and the like. Among them, ethylene, in terms of copolymerization reactivity and alkali solubility, preferably benzene N-phenyl maleimide, N-cyclohexyl maleimide, N-benzyl cis Butylene diimine bicyclo [2.2.1] hept-2-ene and the like. The copolymer [ΚΪΗΚ4] can be referred to, for example, the method described in the "Experimental Method for Polymer Synthesis" (Otsutsu Takayuki, "Chemical Tongren Publishing Co., Ltd., First Printing", issued in 1972...) Manufactured from the cited documents. Specifically, a specific amount of the monomers (B1) and (B2) and any of the copolymers (B3) constituting the copolymer, a polymerization initiator and a solvent are added to the reaction vessel, and oxygen is replaced with nitrogen gas, and oxygen does not exist. The mixture was stirred and twisted to obtain a polymer. The addition method, reaction temperature, and time may be appropriately adjusted in consideration of manufacturing equipment, heat generation of polymerization, etc. under the conditions of 149310.doc • 86 - 201111447. Any of the above-mentioned (4) usual users can be used as the polymerization initiator and solvent used herein. For example, the above polymerization initiator, solvent and the like can be used. Further, the copolymer of # may be used as it is, or a solution obtained by concentration or dilution may be used, or a solid (powder) taken out by a method such as re-sinking may be used. In particular, by using the above solvent as a solvent in the polymerization, the solution after the reaction can be used as it is, so that the production steps can be simplified. The copolymer [Kim is preferably a ratio of the structural unit derived from each monomer to the total number of moles of the structural unit constituting the copolymer [K1] in the following range of 0 (Bl) 5 to 95 mol %'. ~ such as Moer% (B2) 5~95 Moer % 'better for ~ as Moer%. Further, the copolymer [K2] is preferably such that the ratio of the structural unit derived from each monomer is within the following range with respect to the total amount of the structural unit constituting the copolymer [K2]. (81) 2 to 40 mol%, more preferably 5 to 35 mol% (Β2) 2 to 95 mol %' better for $~8〇 Moer% (33) 1~65 mol%, more Jia Wei 丨 ~ 6 〇 Mo Er%. The copolymer [Κ3] can be produced in two stages. First, (Β1) and (Β3) were copolymerized in the same manner as in the above method to obtain a copolymer. In the case of the β If shape, it is preferable that the ratio of the respective monomers is within the following range with respect to the total amount of the structural units constituting the resin. 149310.doc -87- 201111447 (Bl) 5~50% by mole, preferably ι〇~45mol. /〇 (B 3) 50 to 95% by mole, preferably 55 to 90% by mole. Then, a part of the carboxylic acid and/or carboxylic anhydride of (B1) derived from the copolymer of (B1) and (B3) and a cyclic ether derived from (B2) (oxiranyl group, oxetane) The alkyl group or tetrahydrofuranyl group is reacted. In order to carry out the reaction, the inside of the tile is replaced with air by an atmosphere, and (B2), a reaction catalyst, a polymerization inhibitor, and the like are placed in a flask, for example, at 60 to 13 ° C for continued reaction. ~(7) hours. The reaction conditions such as the addition method, the reaction temperature, and the like can be appropriately adjusted in consideration of the manufacturing equipment and the heat generation amount of the polymerization. In this case, the number of moles of (B2) relative to the number of moles of (B1) is preferably 5 to mol%, more preferably H) to 75 mol%, and further preferably 15 to 7 mol%. . The reaction catalyst is preferably used as a reaction catalyst for the m group and the cyclic group (epoxyethyl, oxetane or tetrahydrofuranyl). Specifically, tridecylaminomethylphenol or the like can be exemplified. The amount of the reaction catalyst used is 0.001 to 5 Å/〇 with respect to the total amount of (B1) to (B3). # Polymerization inhibitors, for example, can be exemplified by p-benzoic acid. The amount of the polymerization inhibitor is preferably 0.001 to 5 masses per liter of the total amount of (B 1) to (B3). The copolymer ceramic is preferably a ratio derived from the structural unit of each monomer. The total amount of the monomers constituting the copolymer [K4] is in the following range. 5 (B1) 2 to 40 mol ° °, more preferably 5 to 35 mol % (B2) 60 to 98 mol %, more preferably 65 to 95 mol %. 149310.doc -88· 201111447 The copolymer [K1][K4] dispersion (molecular weight distribution), [weight average molecular weight (MW) / number average molecular weight (?η)] is preferably ι 6 6 〇, more preferably 1 2~4,0 The polystyrene-equivalent weight average molecular weight of the resin (8) is preferably 5, _~35,000', more preferably 6, _~3μ (10), and particularly preferably 7, coffee ~% coffee. When the molecular weight is in the above range, the hardness of the coating film is increased, the residual film ratio is also high, and the solubility of the unexposed portion with respect to the developer is good, and the resolution tends to be improved, which is preferable. The acid value of the resin W. is preferably from 50 to 150, more preferably from 6 to 135, still more preferably from 7 to 135. Here, the acid value is a value measured by neutralizing the amount (mg) of potassium which is necessary for 1 g of the acrylic acid polymer, and can usually be determined by titration with an aqueous solution of potassium hydroxide. The content of the solid content relative to the solid content of the coloring composition is preferably 贝65 berg/twice, more preferably 13 to 6 〇 mass%, still more preferably 17 to 55 mass%. When the content of the tree is within the above range, a pattern can be formed, and the resolution and the residual film ratio tend to increase. The polymerizable compound (c) is not particularly limited as long as it can be polymerized by photopolymerization by irradiation with light, and active polymerization of an initiator (D). For example, a compound having a polymerizable carbon and a bond may, for example, be mentioned. The photopolymerizable compound (C) is preferably a compound having three or more functional groups, and is a compound. Examples of the trifunctional or higher polyfunctional photopolymerizable propylene include, for example, pentaerythritol tetraacrylic acid vinegar, quaternary tetral tetramethylene acrylate, _ &amp; oxime, pentaerythritol pentaacrylate, and dipentaerythritol. Pentamethyl 149310.doc •89- 201111447 Acrylate, dipentaerythritol hexaacrylic acid _ ^ R '- -T· /5, p / m 4^ oleic acid vinegar, etc. The above photopolymerizable compound (c) can be used alone Use two or more. ί : The content of the polymerizable compound (c) is preferably from 7 to 65% by mass, more preferably from 13 to 6% by mass, based on the solid content of the coloring composition. When the content of the photopolymerizable compound (the content of the ruthenium is in the above range, the curing is sufficiently performed, and the film thickness ratio before and after the development: n is less likely to cause undercut in the pattern, and the adhesion tends to be good. The polymerization initiator (9) is a polymerizable compound (the compound which is polymerized by hydrazine is preferably a compound which generates a radical by ultraviolet rays) by generating an active radical, an acid or the like by irradiation with light. As the photopolymerization initiator described above (D) 'A living radical generating agent, an acid generating agent, etc. are mentioned. 'The living radical generating agent generates an active radical by irradiation of light. Examples of the active radical generating agent include an acetophenone system. a compound, a benzoin-based compound, a benzophenone-based compound, a 9-oxo-sulphate compound, a tri-negative compound, an anthraquinone-based compound, etc. As the acetophenone-based compound, for example, diethyl methoxide _, 2-methyl-2-indenyl]-(4·-methylphenyl) propyl ketone ketone-2-methyl small phenylpropane small _, benzoin dinonyl ketal, 2_hydroxy_ 2_mercaptocarboxyethoxy) stupid base] Preferred in the field of Xiaogang, i-radiocyclohexyl phenyl ketone, 2-carbyl-2-methyl W4 methyl ethyl phenyl) phenyl] propyl -1- ketone oligomer, etc. A 2-methyl-julinylmethylthiophenyl) propan-1-one etc. are mentioned. The living radical generator generates active radicals by irradiating light. 149310.doc 201111447 is the above-mentioned living radical generating agent, for example, &amp; benzoin-based person, benzophenone-based compound, 9-oxo-sulfur, human t, P-galaxy compound, tri-11 well-based compound, hydrazine A compound or the like. As the above-mentioned benzoin-based compound, for example, ~ ^ _ 夕 』 ─ ─ ─ ─ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Examples of the benzophenone-based compound include dimercaptoketone, decylcarbenyl benzoate, 4-phenyl-poor s-benzalone, and 4-benzylidene- 4 , · mercapto diphenyl sulfide, 3,3',4,4,-tetra (p-τ * V dibutyl carbonyl peroxide) dibenzophenone, 2,4,6-trimethyl Benzophenone and the like. Examples of the above-mentioned 9-oxothiolane compound include isopropyl isophthalic acid 9-oxosulfanyl star, 4-isopropylsulfoxide (tetra), 2, diethyldi: mountain, 2, and dichloro winter. Oxygen sulfur (four), such as propoxy _9 · bismuth sulphur - and so on. Examples of the above-mentioned three-tillage compound include: 2, bis (trimethyl) W4-methoxyphenyl well, 2,4 bis (trisyl) (4) methyl lactyl naphthyl-1 , 3,5-three-flavor, 2,4-bis(trimethylsulfonyl)_6_(4_methyl-based stupid vinyl)-1,3,5-three tillage, 2,4-bis(trichloromethyl) Winter [2_(5_methyl^ _ 2-yl)vinyl]-l,3,5-three tillage, 2,4-bis(trimethylsulfonyl)_6_[2_(bitanyl)vinyl]- 1,3,5-three tillage, 2,4-bis(trioxanemethyl)_6_[2_(4_diethylamino-2-mercaptophenyl) vinyl b ^, ^ three tillage, 2, 4_bis(trichloromethyl I 6-[2·(3,4-dimethoxyphenyl)vinyl tritonate. For example, as the above-mentioned quinone compound, 〇 醯 醯 肟 肟 化合物As a specific example thereof, N_benzhydryloxy^-(heart phenylsulfanylphenyl)butan-1-one-2-yenampron, N-benzidineoxy-b (4_Stupid sulfur

-9U I49310.doc t 201111447 alkylphenyl)octane-1-one-2-imine, N_acetoxy_i_[9ethyl_6_(2 mercaptobenzoyl)-9H- Oxazole·3_yl]ethaneimine, N-acetoxy- 1-[9-ethyl-6-{2-methyl-4-(3,3-dimercapto-2,4 - Dioxolyl methoxy) phenyl hydrazone}-9 Η-carbazole · 3 · yl] ethaneimine and the like. Further, as the living radical generating agent, for example, 2,4,6•trimercaptophenylphosphonium diphenylphosphine oxide, 2,2,_bis(o-phenyl)-4,4,5 may be used. 5,-Tetraphenyl-1,2'-biimidazole, 10-butyl-2_acridinone, 2-ethyl oxime, stupid oxime, 9,10-phenanthrenequinone, camphorquinone, phenyl Ethyl glyoxylate, titanium titanate compound, and the like. . Examples of the acid generator include p-toluenesulfonic acid 'hydroxyphenyl dimethyl hydrazine, hexafluorodecanoic acid 4-hydroxyphenyl dimethyl nickel, and p-toluene sulfonic acid 4-acetoxy phenyl benzene. Sulfhydryl nickel, hexafluoroantimonic acid 4_acetoxyphenyl•methyl·benzyl hydrazine, triphenyl sulfonate p-toluene, triphenyl sulfonium hexafluoroantimonate, diphenyl hydrazine And rust salts such as hexafluoroantimony diphenyl hydrazine and sulfhydryl sulfonate/salt, benzoin benzenesulfonate/salt. Further, as the above-mentioned living radical generating agent, the above-mentioned compound is also a compound which generates an acid at the same time as the generation of a radical, and for example, a tri-grain photopolymerization initiator can also be used as an acid generator. The content of the photopolymerization initiator (D) is preferably 0 丨 to "% by mass", more preferably 1 to mas., if the photopolymerization initiation is started with respect to the lyophilized resin of the alkali-soluble resin and the photopolymerizable σ (c). When the content of the agent is in the above range, the sensitivity is improved, and the exposure time is shortened, and the productivity is improved. The coloring composition of the present invention may further contain a photopolymerization initiation aid (F). Photopolymerization initiation aid (F) It is usually used in combination with a photopolymerization initiator to use 149310.doc-92·201111447 as a compound or sensitizer for promoting polymerization of a photopolymerizable compound which starts polymerization by a photopolymerization initiator. Examples of the starting auxiliaries (F) include an amine compound, an alkoxy fluorene compound, and a 9-oxo sulphide p star compound. Examples of the amine compound include triethanolamine and methyldiethanolamine. , triisopropanolamine, 4-dimethylaminobenzoic acid decyl ester, decarboxylated aminobenzoic acid ethyl 4-, 4-dimethylamino-based stearic acid isoamyl, benzoic acid _ 2- Dimethylamino-based, 4_: methylamino-based stearic acid ethyl hexanoic acid, N,N-dimethyl-p-phenylene , 4,4,_bis(dimethylamino)benzamide (commonly known as micbutone), 4,4,-bis(diethylamino) dioxin, 4,4, _ double (ethylmethylamino)diphenyl hydrazine _ and the like, among which 4,4·-bis(diethylamino)benzophenone is preferable. Examples of the alkoxy quinone-based compound include, for example, 9 , bis-indenyl, 2-ethyl-9,10-didecyloxy fluorene, its, ιυ--ethoxy hydrazine, 2-ethyl-9,10-diethoxy hydrazine, 9,1 〇 Dimethyl ketone, 2-ethyl-9,10-dibutoxy oxime. Examples of the above 9-oxothiolane compound include 2-isopropyl-9-oxathione, 4·. Isopropyl oxysulfide, hawthorn, 2 丨g, monoethyl-9-oxopurine, 2,4-dichloro_9_oxathiazin p, ^chloro^^'propoxy-9- Oxygen and sulfur U mountain p-star temple. Photopolymerization start-up aid (F) can be used alone, ^ ^ s can also be used in combination, and the optical start-up auxiliary (F) is also used 1 As a commercially available first &amp; initial starter (F), for example, 土 谷 谷 和 和 gong + 商口 0 "EAB-F" (made by Baotu Guhua Industrial Co., Ltd.), etc. 149310.doc - 93- 201111 447 As a combination of a photopolymerization initiator (D) and a photopolymerization initiation aid (ρ), for example, diethoxyacetophenone/4,4,-bis(diethylamino)di Alum ketone, 2-methyl-2-mi-yl-1-yl-1-(4-indolethiophenyl)propan-1-yl ketone/4,4,-bis(diethylamino) dioxin , 2-hydroxy-2-mercapto-1-indolyl propan-1-one/4,4'-bis(diethylamino)benzophenone, acne dinonyl ketal/4,4 , bis(monoethylamino)-one fluorenone, 2-transyl-2-mercapto-l-[4-(2-carbylethoxy)phenyl]propan-1-one/4, 4'-bis(diethylamino)benzophenone, hydroxycyclohexyl phenyl ketone / 4,4·-bis(diethylamino)benzophenone, 2-hydroxy-2-methyl- Oligomer of l-[4-(l-fluorenylvinyl)phenyl]propanone oxime-ketone/4,4,·bis(diethylamino)dimercapto ketone, 2-benzyl _ 2_dimethylamino _ 丨 _ (4 • morpholinyl phenyl) butan-1-one / 4,4,-bis (diethylamino) benzophenone, etc., preferably listed 2_Methylmorpholinylphosphonium phenyl)propane oxime / 4,4'-bis(diethylamino)benzophenone. In the case of using the photopolymerization initiation aid (F) ester, the amount thereof is preferably from 〜1 to 10 mol per 1 mol of the photopolymerization initiator (D), more preferably 0.01 to 5 moles. The sub-Asian is not particularly limited, and a solvent which is usually used in the field can be used. The above solvent can be appropriately selected and used. The cold agent (E) as the coloring composition preferably contains a group selected from the group consisting of propylene glycol monoacetic acid acetoacetate monomethyl ether, cyclohexanone 'lactic acid ethyl vinegar, and 4, yl group. ? # Μ % 醢 , , , , , , , , , ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' 4 .. six system ^ more preferably έ 丙 丙 单 单 单 单 酉 酉 酉 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 丙 # # # # # I I I I I I I I I I I I I I I I I I The content of the solvent (E) in the coloring composition is 70 to 95% by mass, more preferably 75 to 92% by mass based on the coloring composition. In other words, the solid content is relative to the coloring composition. 5 to 30% by mass, preferably 8 to 25% by mass. If the content of the solvent (E) is in the above range, the flatness at the time of coating becomes good, and the color density is not insufficient when the color filter is formed. Therefore, the display characteristics tend to be good. The coloring composition of the present invention may optionally contain a surfactant (G) ( It is different from the pigment dispersant.) As the surfactant (G), a surfactant having a deficient atom or an oxime atom is suitable. Specific examples thereof include a polyoxo-based surfactant and a fluorine-based surfactant. And at least one of the group consisting of a polyfluorene-based surfactant having a fluorine atom. The polyfluorene-based surfactant may, for example, be a surfactant having a decane bond. Specific examples thereof include Toray. Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA 'Toray Silicone SH28PA ' Toray Silicone SH29PA ' Toray Silicone SH30PA &gt; Toray Silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd.); KP321 'KP322, KP323, KP324, KP326 , KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan), etc. Agent, can be listed as having a fluorocarbon chain interface activity 149310.doc • 95-2 01111447, etc. Specific examples include: Fluorad (trade name) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.); Megaface (trade name) F142D, Megaface F171, Megaface F172, Megaface F173, Megaface F177, Megaface F183, Megaface F489, Megaface F554, Megaface R30 (manufactured by DIC Corporation); Eftop (trade name) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.); Surflon (trade name) S381, Surflon S382 , Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.); E5844 (manufactured by Daikin Fine Chemical Research Co., Ltd.); bM-1000, BM-1100 (all trade names, manufactured by bm Chemie). Examples of the polyfluorene-based surfactant having a fluorine atom include a surfactant having an anthracycline bond and an I carbon chain. Specific examples include Megaface (registered trademark) R〇8, Megaface BL20, Megaface F475, Megaface F477, Megaface F443 (manufactured by DIC Corporation), and the like. These surfactants may be used singly or in combination of two or more. The content of the surfactant (G) is preferably 0.0005 to 0.3 parts by mass, more preferably 〇〇〇1 to 〇1 part by mass, per part by mass of the coloring composition. When the content of the surfactant (F) is in the above range of 0, the flatness tends to be good. The coloring composition of the present invention is preferably a negative coloring composition. The colored composition of the present invention can be suitably used for a silk color filter or a colored pattern to obtain a good color pattern such as color density, brightness, contrast, sensitivity, resolution, and resistance to heat resistance of 1493l.d〇c •96·201111447 heat. And color filters. Further, the coloring composition of the present invention can be used in an optical film, an array substrate, a color light-receiving substrate, or the like having such a color filter or a colored pattern as a component thereof, and the like. Display devices such as a color filter or a coloring pattern, an optical film or an array substrate, and a color filter substrate, for example, a known liquid crystal display device, an organic EL (electroluminescence) device, a solid-state imaging device, and the like Like related equipment. As a method of forming a color filter or a pattern thereof using the coloring composition of the present invention, for example, the coloring composition of the present invention may be applied to a substrate or another resin layer (for example, another coloring composition layer previously formed on the substrate) The method of removing or drying a volatile component such as a solvent to form a colored layer, exposing the colored layer to a developed layer via a photomask, and a method of using an inkjet apparatus without photolithography. The film thickness of the coating film in the case of the sea is not particularly limited, and can be appropriately adjusted depending on the material used, etc., for example, 〇1 to 3 〇, preferably μηηι ′, and more preferably 6 μm. Examples of the coating method of the color composition include an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, a P-prime, a calcium phosphate coating method, a die coating method, and the like. Further, a dipping coater, a bar coater, a rotary coater, a slit &amp; spin coater, and a slit coater (sometimes referred to as a die coater, a curtain type flat coater, or a non-use) may be used. Coating is performed by a coater such as a spin coater (spinless chopper). Among them, it is preferred to apply using a spin coater. The solvent removal/drying can be exemplified by natural drying, ventilating and drying, and 149310.doc •97·201111447 pressure drying. The specific drying temperature is preferably I0~120t, and the f is preferably 4 25~1001 dry (four) preferably between 1 () seconds and 6 () minutes better (four) seconds. In the case of drying under reduced pressure, it is preferably at a pressure of 5 Torr to 150 Pa at 20 to 25. (In the temperature range of the following: Example: Hereinafter, the method for producing the pigment dispersion liquid of the present invention, the method for producing the coloring composition, and the color for the color pattern of the A 荽ώ λ cloud are performed by &lt;&lt;&gt; The filter and the like are described in more detail. "%" and "part" in the examples are masses and/or parts unless otherwise specified. Synthesis Example 1 &lt;Synthesis of Dye Α1&gt; In the flask of the tube and the stirring device, 15 parts of the pigment (manufactured by Sino-foreign Chemical Co., Ltd.), 150 parts of sputum, and 8.9 parts of hydrazine, dimethyl dimethyl carbamide were added to the flask of the stirring apparatus. (10) or less, 10.9 parts of sulfite gas was added dropwise to the surface, and after the completion of the dropwise addition, the temperature was raised to 5 〇〇c, and the reaction was continued at the same temperature for 5 hours, and then cooled to 2 〇t: The reaction solution after cooling was maintained at 20. The mixture of 12.5 parts of 2:-hexylamine and 22.1 parts of triethylamine was added dropwise thereto, and the mixture was stirred at the same temperature for 5 hours to carry out a reaction. The evaporator of the reaction mixture is distilled off by the evaporator. Add a small amount of a to the ^ ^ i τ drunk and stir vigorously. While stirring, add the mixture to a mixture of 375 parts of ion-exchanged water to precipitate crystals. The precipitated crystals are separated by filtration and carefully washed with ion-exchanged water. Net, dry under reduced pressure at 6 ° C, and obtain dye 1493IO.doc -98- 201111447 A1 (Dye A1-1 ~ dye A1_8 mixed dye Sichuan 3 parts · AO-1

A1

(In the formula (Al), Rc independently represents _s〇2iNjH Ra, or, H; Ra represents 2_ethylhexyl).

AM

A1-2

M93I0.doc -99· 201111447 Synthesis Example 2 <Synthesis of Resin B1> 133 g of propylene glycol monoterpene ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube, and the flask was placed therein. The environment is replaced by air into nitrogen. The temperature was raised to 10 ° C, and it was added dropwise to a monodecyl acrylate containing 82.8 g (0.47 mol) of benzyl methacrylate, 37.0 g (0.43 mol) of methacrylic acid, and a tricyclodecane skeleton (Hitachi Chemical Co., Ltd. Manufactured by Co., Ltd., FA-513M) a solution of 2,2·-azobisisobutyronitrile 3.6 g in a mixture of 22.0 g (0.10 mol) and propylene glycol monoterpene ether acetate 164 g, and further Continue stirring at 1 〇〇t. Then, the environment inside the flask was replaced with nitrogen by nitrogen, and glycidyl methacrylate 2 1.5 g [0.1 5 mol (relative to the carboxyl group of the mercaptoacrylic acid used in the reaction was 5 〇mol/〇)] , tris-didecylamino nonylphenol oxime 9 g and hydroquinone hydrazine 145 g were put into the firing plate to continue the reaction at 11 to obtain a resin solution B1 having a solid content of 97 mg KOH/g of solid content (solid form) Composition: 38%). The polystyrene-equivalent weight average molecular weight of the above-mentioned resin is determined by GPC (gel permeation chromatography, gel permeation chromatography). The GPC method was carried out under the following conditions. Device, :HLC-8120GPC (Tosoh) tube string column temperature

Manufactured by Ltd.) TSK-GELG2000HXL 40°C 149310.doc 100· 201111447 Solvent: THF (tetrahydrofuran, tetrahydrofuran) Flow rate: 1.0 mL/min . Solid content of test solution: 0.001~0.01% by mass Quantity: 50 μιm Detector: RI (Refractive Index)

Standard material for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, Fl, A-2500, A-500 (manufactured by Tosoh Co., Ltd.) Examples 1 and 2, Comparative Examples 1 and 2 &lt;Production of pigment dispersion &gt; The components described in Table 22 were sequentially placed in a beaker, and all the components were mixed. Thereafter, a oxidized bead of 〇 · 6 5 mm # was used, and a dispersion treatment was performed for 5 hours by a coating shaker. The resulting uniform dispersion was filtered to remove the beads to obtain a pigment dispersion. [Table 22] Example 3 Example 4 Comparative Example 1 Comparative Example 2 Pigment Dispersion 1 2 3 4 Pigment 4.35 4.35 5.0 5.0 Dye 0.68 0.68 0 0 Dispersant 1 6.68 6.68 6.68 6.68 Dispersant 2 0.145 0.145 0.167 0.167 Solvent 1 17.71 0 17.71 0 Solvent 2 0 17.71 0 17.71 149310.doc .101 - 201111447 Example 1 Example 2 Comparative Example 1 Comparative Example 2 Pigment Dispersion 1 2 3 4 Pigment (parts) 4.35 4.35 5.0 5.0 Dyes (parts) 0.68 0.68 0 0 Dispersant U) 6.68 6.68 6.68 6.68 Dispersant 2 (parts) 0.145 0.145 0.167 0.167 Solvent 1 (parts) 17.71 0 17.71 0 Solvent 2 (parts) 0 17.71 0 17.71 Pigment: CI Pigment Blue 15:6 Dyes: Dyes A1 Dispersant 1: Disperbyk-1 61 (manufactured by BYK Chemie Co., Ltd.) Dispersant 2: Copper ugly cyanine derivative (manufactured by Solsperse 5000 'Availa Co., Ltd.) Solvent 1: Propylene glycol monomethyl ether acetate solvent 2: Ethyl lactate Example 3 to 5, Comparative Examples 3 to 5 &lt;Production of Coloring Composition&gt; The components described in Table 23 were mixed to obtain a coloring composition. [Table 23] Example 3 Example 4 Example 5 Comparative Example 3 Comparative Example 4 Comparative Example 5 Pigment Dispersion 1 (part) 23.7 0 26.3 0 0 0 Pigment Dispersion 2 (parts) 0 26.4 0 0 0 0 Pigment dispersion Liquid 3 (parts) 0 0 0 20.6 0 22.9 Pigment dispersion 4 (parts) 0 0 0 0 22.9 0 Dye A1 (parts) 0 0 0 0.5 0.6 0.6 Resin solution B1 (parts) 14.2 15.7 15.7 14.4 16.0 16.0 Photopolymerizability Compound (parts) 5.3 5.9 5.9 5.4 6.0 6.0 Photopolymerization initiator (parts) 1.6 1.8 1.8 1.6 1.8 1.8 Surfactant (parts) 0.009 0.01 0.01 0.009 0.01 0.01 Solvent 1 (parts) 0 0 50.2 0 0 52.7 Solvent 2 ( Part) 0 50.2 0 0 52.7 0 Solvent 3 (parts) 55.2 0 0 57.4 0 0 149310.doc • 102· 201111447 Example 5 Example 6 Example 7 Comparative Example 3 Comparative Example 4 Comparative Example 5 Pigment Dispersion (Type) 1 2 1 3 4 3 Pigment Dispersion (Amount) 23.7 26.4 26.3 20.6 22.9 22.9 Dye 0 0 0 0.5 0.6 0.6 Resin 14.2 15.7 15.7 14.4 16.0 16.0 Photopolymerizable compound 5.3 5.9 5.9 5.4 6.0 6.0 Photopolymerization initiator 1.6 1.8 1.8 1.6 1.8 1.8 interface active agent 0.009. 0.01 0.01 0.009 0.01 0.01 dissolve 1 0 0 50.2 0 52.7 0 50.2 0 0 0 Solvent 2 Solvent 3 55.2 52.7 0 57.4 0 0 0 0 Table 23 'of each component are as follows. Photopolymerizable compound: diquaternary pentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) Photopolymerization initiator: Ν-benzylideneoxy-1-(4-phenylsulfanylphenyl)octane 1-嗣-2-imine (Irgacure ΟΧΕ01; manufactured by Ciba Specialty Chemicals) Surfactant: Polyether modified polyoxygenated oil (SH8400, manufactured by Dow Corning Toray Co., Ltd.) Solvent 1 : propylene glycol monoterpene ether acetate solvent 2 : ethyl lactate solvent 3 : 4-hydroxy-4-mercapto-2-pentanone &lt;Production of color filter&gt; By spin coating method, the above obtained The coloring composition was applied to a glass substrate (Eagle 2000, manufactured by Corning) of 2 ying. 1493I0.doc -103- 201111447 Then, in a dust-free oven, pre-bake for 10 minutes at 10 (rc. After cooling, use an exposure machine (TME-150RSK, manufactured by Topcon Co., Ltd.) at 150 mJ in the atmosphere) /cm2 exposure amount (365 11 is called light irradiation, and it is heated at 22 〇t for 20 minutes to prepare a color filter. The color filter is measured using a membrane-testing device (DEKTAK3, manufactured by Nippon Vacuum Technology Co., Ltd.) Film thickness of the light sheet. [Evaluation of foreign matter] The surface of the obtained color filter was visually confirmed. Those who had no foreign matter at all were evaluated as 〇, those with a small amount of foreign matter were evaluated as Δ, and those who saw a large amount of foreign matter were evaluated as x. The film having a large amount of foreign matter and being incapable of obtaining a uniform film was evaluated as xx. The results are shown in Table 24. [Brightness Evaluation] Using a color measuring machine (OSP-SP-200; manufactured by Olympus Co., Ltd.) The spectrum was measured by light, and the xy chromaticity coordinates (x, y) and luminance γ of the XYZ color system of CIE (Commission International de I'Eclairage, International Commission on Illumination) were measured using a C light source. The result is not in Table 24. [ Evaluation of the color filter obtained by sandwiching two polarizing plates (POLAX-3 8S; manufactured by Luceo Co., Ltd.) using a contrast measuring device (CT-1, manufactured by Kesaka Electric Co., Ltd.) and a luminance meter ( BM_5A, manufactured by T〇pc〇n Technohouse Co., Ltd.), a cold cathode tube F10 lamp as a light source' measures the brightness of the transmitted light of the sample under parallel polarized light and the brightness under orthogonal polarized light, and the brightness under parallel polarized light The ratio of the brightness to the polarized light is 149310.doc -104· 201111447 (parallel polarized/orthogonal polarized light) as the contrast. Furthermore, before the contrast of the color filter is measured, so as not to sandwich the color filter The intensity of the light source was adjusted in such a manner that the contrast measured was 10,000. The results are shown in Table 24. [Table 24] Example 3 Example 4 Example 5 Comparative Example 3 Comparative Example 4 Comparative Example 5 Foreign matter 〇Δ 〇 XX XX film thickness (μιη) 1.72 1.83 1.63 2.14 1.94 - X 0.145 0.144 0.145 0.154 0.146 - y 0.100 0.100 0.100 0.100 0.100 - Υ 11.2 10.9 11.5 11.3 10.9 - Contrast 1778 1106 1446 1224 943 Lu Example 5 Example 6 Example 7 Comparative Example 3 Comparative Example 4 Comparative Example 5 Foreign matter 〇Δ 0 XX XX Film thickness (μιη) 1.72 1.83 1.63 2.14 1.94 - X 0.145 0.144 0.145 0.154 0.146 - y 0.100 0.100 0.100 0.100 0.100 - Υ 2 2 778 778 778 778 778 778 778 778 778 778 After adding 75 parts of water, 2.0 parts of sodium hydroxide was added to dissolve it. Under ice cooling, 9.5 parts of an aqueous solution of 35% sodium nitrite (manufactured by Wako Pure Chemical Industries Co., Ltd.) was added, followed by gradually adding 30.0 parts of 35% hydrochloric acid to dissolve it, and stirring for 2 hours to obtain a salt containing diazonium rust. Suspension 149310.doc -105 - 201111447 liquid. Then, an aqueous solution obtained by dissolving 8.9 parts of an aminosulfonic acid (manufactured by Wako Pure Chemical Industries Co., Ltd.) in 36 parts of water was gradually added, and the excess sodium arginate was quenched. Then, 13 parts of '3-mercaptosulfonyl)-5-pyrazolone (manufactured by Wako Pure Chemical Industries, Ltd.) was suspended in 100 parts of water, and the pH was adjusted to 8 使用 using sodium hydroxide. . In the above, a 10% sodium hydroxide solution was appropriately added so that the value of {)1_1 was controlled within the range of 7 to 7, 5, and the suspension containing the diazonium salt was added dropwise over 15 minutes. After the completion of the dropwise addition, the mixture was further stirred for 30 minutes, whereby a yellow suspension was obtained. Stir for 1 hour. Filtration gave a yellow solid, and the yellow solid was dried at 6 (rc) under reduced pressure to obtain 17 parts of the compound of formula (p-1) (yield: 85%):

Add 10 parts of the compound of the formula (P-1) to 100 parts of dimercaptocarboxamide (manufactured by Tokyo Chemical Industry Co., Ltd.) to dissolve it, and add ammonium (III) sulfate dodecahydrate (Wako Pure Chemical Industries, Ltd.) 31 parts, manufactured by Co., Ltd., and U parts of sodium acetate (manufactured by Wako Pure Industries Co., Ltd.), and heated under reflux for 4 and a half hours. After cooling to room temperature, the reaction solution was poured to 20. /. After 1500 parts of brine, an orange-red solid was obtained by filtration, and the orange-red solid was dried under 6 〇 &lt;&gt;c to obtain 12 parts of the compound of the formula (z-1) (yield 60%): I49310.doc 106· 201111447

© (ζ·1) Na Adding anhydrous chloroform (manufactured by Kanto Chemical Co., Ltd.) to 17 parts of Rose Red Β (manufactured by Tokyo Chemical Industry Co., Ltd.), 17 parts of camphorsulfonic acid (manufactured by Aldrich Co., Ltd.) 1 . 〇, 4-(Ν,Ν-didecylamino) 0-pyridinium (manufactured by Tokyo Chemical Industry Co., Ltd., 4 parts, triethylene glycol (manufactured by Wako Pure Chemical Industries Co., Ltd.), 18 parts, After stirring for about 30 minutes, it was gradually added to 10.5 parts of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (manufactured by Wako Pure Chemical Industries Co., Ltd.). Add 47 parts of pre-dissolved solution of anhydrous gas, and then stir at room temperature for about 2 hours. After two times of liquid separation operation with 150 parts of 1 Ν hydrochloric acid aqueous solution, use organic solution of 10 ° / brine. The layer was washed twice. Then, 43 parts of anhydrous magnesium sulfate was added, and after stirring for about 30 minutes, the desiccant was filtered, and the solvent was distilled off, thereby obtaining 20.6 parts of the compound represented by the formula (g-indole) (yield 90) °/〇) Identification of the compound represented by formula (g-1) (mass sigma analysis) ionization mode = ESI+ : m /z=575.3 [M-C1·]. Exact Mass: 610.3

149310.doc • 107- 201111447 Add 4 to 3 parts of decyl alcohol to 253 parts of the compound shown in formula 1) to prepare a cold liquid (si). Further, methanol (1) was added to 153 parts of the compound represented by the formula (g)) to prepare a solution ((1). Thereafter, the solution (4) was read at room temperature (4) to read the solution (1)), and the mixture was stirred for about 1 hour. The red solid formed by the citric acid was dried under reduced pressure at 6 (TC), washed with water (3 parts), filtered, and dried under reduced pressure to obtain a compound of the formula (1_) (dye A2). 263 parts (yield is 65%). The structure of the compound represented by 弋(1) is determined by elemental analysis. The analytical preparation system uses an ICP (Inductively Coupled Plasma) luminescence analyzer (ICPS). -8100; manufactured by Shimadzu Corporation, Inc.) C. 55.6, Η: 4.7, N: 12.0, Cr: 3.57

Synthesis Example 4 &lt;Synthesis of Dye A3&gt; After adding 200 parts of water to the toluidine-4-sulfonic acid 1 〇. 〇 part of the formula (a-2), the mixture was cooled to 30% in an ice bath. The operation of adjusting the pH to 8 or less with an aqueous sodium hydroxide solution was carried out under ice bath cooling. Add sodium nitrite • 1 injury and mix for 3 minutes. Gradually add a small amount of 3 5 ° /. 3 9 · 0 parts of hydrochloric acid, shape 149310.doc 201111447 After the brown solution was stirred, for 2 hours. An aqueous solution obtained by dissolving 1 part of the aminosulfonic acid in 101 parts of water is added to the reaction solution, and is searched off to obtain a suspension containing a diazonium salt: ho3s NH2 (a-2) C-2) 1-(2-ethylhexyl)-3-cyano-4-methylhydroxypyridin-2-1 14.0 parts of water added; part and N_mercaptopyroline 25 〇 After the portion was cooled in an ice bath, the pH was adjusted to 3 〇% aqueous sodium hydroxide solution.

The following operations were carried out under ice bath cooling. After stirring the above pyridone to dissolve into a colorless solution,

After the float &amp; :* solution, the pH was pumped with a 30% aqueous solution of sodium hydroxide, and the heart τ containing the diazonium salt was added dropwise over 2 hours. After completion of the dropwise addition, the mixture was further stirred for 2 hours to obtain a yellow suspension. The yellow solid was obtained by filtration, and the yellow solid was dried at 60 ° C under reduced pressure to obtain 21.4 parts of the compound of formula (d-3) (yield: 87%):

149310.doc 201111447 Compound (d-3) 0.35 g was dissolved in N,N-dimethylformamide to make a body

100 cm3 (concentration: 0.028 g/L), and the absorption spectrum was measured using a spectrophotometer [quartz cell, the length of the groove was 1 cm]. The compound showed an absorbance of 2.9 (arbitrary unit) at human max = 433 nm. 5.0 parts of the compound (d_3), 35 parts of acetonitrile, and N,N-dimethylformamide ι_6 parts were placed in a flask equipped with a condenser and a stirring device, and the mixture was kept at 20 ° C or lower while stirring, and added dropwise thereto. Thionite is 2.4 parts. After the completion of the dropwise addition, the temperature was raised to 40 ° C, and the reaction was carried out for 2 hours at the same temperature, followed by cooling to 20 ° C. While stirring, the cooled reaction solution was poured into 150 parts of ice water, and stirred for 30 minutes. The precipitated yellow crystals were separated by filtration, washed carefully with tap water, and dried at room temperature for a few hours. In addition, a flask having a condenser and a stirring device was prepared, and 20 parts of an amine base 2 -propanol and 20 parts of N-methylpyrrolidone were added, and the mixture was maintained at 2 μm or less while stirring, and the above-mentioned one hour was charged. The yellow crystals were prepared. After the yellow solid was charged, the temperature of the solution was raised to room temperature, and then the reaction solution was stirred for 3 minutes. After adding 4 parts of methanol to the reaction solution and stirring, the mixture was stirred while adding the mixed solution to a mixture of 29 parts of acetic acid and 3 parts of ion-exchanged water to precipitate crystals. The precipitated crystals were separated by filtration, washed carefully with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 3.9 parts of a compound of formula (3) (yield: 69%):

149310.doc •110· 201111447 The compound (ΙΠ-3)〇·35 g was dissolved in ethyl lactate to a volume of 250 cm3, and 2 cm3 of the solution was diluted with ion-exchanged water to a volume of 100 cm3 (concentration). : 0 028 g/L), the absorption spectrum was measured using a spectrophotometer (quartz cell, optical path length: 1 cm). The compound showed an absorbance of 2.3 (arbitrary unit) at Xmax = 431 nm. The following reaction was carried out under a nitrogen atmosphere. After adding N-methylpyrrolidone 4·〇 to the compound (ιπ_3) 2 parts, the mixture was stirred for 3 minutes to prepare a reaction solution. While stirring the reaction solution at room temperature, add 1 part of hydrazine gas. After the completion of the dropwise addition, the mixture was further stirred for 8 hours. After the reaction solution was poured into 300 parts of water, 8 parts of ethyl acetate was added and stirred for 3 minutes. The organic phase was separated using a separatory funnel, and then washed with 5 parts of water, 500 parts of a 1% aqueous sodium carbonate solution, 5 parts of a 10% aqueous acetic acid solution, and 5 parts of ion-exchanged water. The solvent of the separated organic phase is distilled off to obtain 2.0 parts of the dye A3 represented by the formula (1-6); the yield is 85%: ^ i /~ — / \ h〇v — (_ 0 compound (1-6) The structure was determined by mass spectrometry. The mass spectrometer was JMS-700 (manufactured by JEOL Ltd.) Mass spectrometry: ionization mode = FE) + : m/z = 12 〇〇 compound (1) -6) 0.35 g is dissolved in ethyl acetate to make the volume reach 250 cm, and 2 cm3 of the solution is diluted with ion-exchanged water to a volume of 100 cm3 (concentration: 0.028 g/L) using a spectrophotometer ( Quartz bath, 149310.doc 201111447. Xuan compound at Xmax = 43 1 optical path length: 1 cm) The absorbance (existing unit) of 2.2 is measured under the absorption spectrum. Synthesis Example 5 &lt;Synthesis of Resin Solution B2&gt; Flask of Reflow Cooler and Dropping Funnel

In the case of a mixer, a thermometer, and a reactor, 9.5 parts by mass of 0.02 L/min, and 935 parts by mass of the ester are mixed, _ (the compound represented by the following formula (1-1 -1) and the formula (1_丨) _2) The compound shown was prepared by mixing 24 parts by mass of a molar ratio of 50:50, and 14 parts by mass of ethyl lactate, and the solution was added dropwise to the solution for 4 hours using a dropping funnel. The flask was kept at 70 ° C. On the other hand, using another dropping funnel', the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) 30 mass damage was dissolved in 22 parts by mass of ethyl lactate. The resulting solution was added dropwise to the flask over 4 hours. After completion of the dropwise addition of the solution of the polymerization initiator, it was kept at 70 ° C for 4 hours, and then cooled to room temperature to obtain a weight average molecular weight Mw of 9.0 χ 103, a solid content of 26% by mass, and a solution acid value of 32. Mg-KOH/g resin solution B2:

(1-1-1) (1-1-2) Synthesis Example 6 &lt;Synthesis of Resin Solution B3&gt; 149310.doc 112 201111447 A flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a gas introduction tube 250 parts by mass of propylene glycol monoterpene ether acetate was introduced. Thereafter, nitrogen gas was introduced into the flask using a gas introduction tube, and the atmosphere inside the flask was replaced with nitrogen. Thereafter, after the solution in the flask was heated to 1001, the dropping funnel was used to contain 1 5 2 -6 parts by mass of benzyl methacrylate, 41. 7 parts by mass of methacrylic acid, and 1.5 mass of azobisisobutyronitrile. A mixture of 50 parts by weight of propylene glycol monoterpene ether acetate was added dropwise to the flask over 2 hours, and after the completion of the dropwise addition, the mixture was further stirred at 100 ° C for 2.5 hours to obtain a weight average molecular weight Mw of 2.3 XI04. The solid content component was 34% by mass, and the solution acid value B3 was 47 mg-KOH/g. Examples 6 and 7 &lt;Production of Pigment Dispersion&gt; The components described in Table 25 were sequentially placed in a beaker, and all the components were mixed. Thereafter, 0.65 ιηιηφ of oxidized beads was used, and dispersion treatment was carried out for 5 hours by a coating shaker. The beads were removed by a uniform dispersion obtained by hydrazine to obtain pigment dispersions 5 and 6. [Table 25] Example 6 Example 7 Pigment Dispersion 5 6 Pigment 2 (parts) 2.10 0 Pigment 3 (parts) 0 2.10 Dyes A2 (parts) 0.90 0 Dyes A3 (parts) 0 1.40 Dispersant 3 (parts) 0.79 0.53 Resin Solution B3 (parts) 0.59 0.63 Solvent 1 (parts) 11.52 11.75 149310.doc -113- 201111447 Pigment 2 : CI Pigment Red 254 Pigment 3 : CI Pigment Green 58 Dispersant 3 : Acrylic Pigment Dispersant Solvent 1: Propylene Glycol Monomethyl Ether Acetate Examples 8 and 9 &lt;Production of Coloring Composition&gt; The components described in Table 26 were mixed to obtain a coloring composition. [Table 26] Example 8 Example 9 Pigment Dispersion 5 (parts) 24.11 - Pigment Dispersion 6 (parts) 0 21.32 Resin Solution B2 (parts) 8.62 9.75 Photopolymerizable Compound (Parts) 3.15 3.37 Photopolymerization Starter (Parts) 0.95 1.01 Surfactant (parts) 0.009 0.009 Solvent 1 (parts) 63.16 60.19 Solvent 4 (parts) 0 4.35 In Table 26, the respective components are as follows. Photopolymerizable compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) Photopolymerization initiator: N-benzylideneoxy-1-(4-phenylsulfanylphenyl) octane 1-keto-2-imine (Irgacure OXE01; manufactured by BASF Japan Co., Ltd.) Surfactant: Polyether modified polysulfuric acid (SH8400, manufactured by Dow Corning Toray Co., Ltd.) Solvent 1: propylene glycol monoterpene ether Acid ester solvent 4: cyclohexanone 149310.doc -114- 201111447 &lt;Production of color filter&gt; The coloring composition was applied to a glass substrate of 2 inches square by spin coating (Eagle 2000, Corning) Made). Then, it was prebaked at 100 ° C for 3 minutes in a dust-free oven. After cooling, it was irradiated with an exposure apparatus (TME-150RSK, manufactured by Topcon Co., Ltd.) at 150 mJ/cm 2 (365 nm) in an atmosphere, and heated at 230 ° C for 30 minutes. Color filter. The foreign matter, brightness, and contrast were evaluated in the same manner as in Example 5 for the obtained color filter. [Contrast evaluation] The obtained color filter was sandwiched between two polarizing plates (POLAX-38S; manufactured by Luceo Co., Ltd.), and a contrast measuring device (CT-1, manufactured by Kesaka Electric Co., Ltd.) and a brightness meter (BM) were used. -5A, manufactured by Topcon Technohouse Co., Ltd.), a cold cathode tube F10 lamp as a light source, measuring the brightness of the transmitted light of the sample under parallel polarized light and the brightness under orthogonal polarized light, and the brightness and orthogonal polarization under parallel polarized light. The ratio of brightness (parallel polarization/orthogonal polarization) is used as the contrast. The results are shown in Table 27. Further, before measuring the contrast of the color filter, the intensity of the light source was adjusted so that the contrast measured in the state where the color filter was not held was 30,000. [Table 27] Example 8 Example 9 Foreign material 〇〇 film thickness (μηι) 1.72 1.92 X 0.650 0.313 y 0.315 0.595 Υ 17.2 63.7 Contrast 13941 19187 149310.doc • 115· 201111447 Using Examples 3 to 5, 8 and 9 By coloring the composition, a good color filter having less foreign matter can be obtained. Further, it was confirmed that the color filter has excellent brightness and contrast. On the other hand, a large amount of foreign matter was generated in Comparative Examples 3 to 5. Further, the value of x is large, and the chromaticity of reddishness is also caused, and the contrast is also poor. In particular, in Comparative Example 5, the normal evaluation was impossible due to the large amount of foreign matter. INDUSTRIAL APPLICABILITY The method for producing a pigment dispersion liquid of the present invention can uniformly disperse dyes and pigments by a simple method, and thus can be widely used in various manufacturing processes not limited to semiconductor manufacturing processes and the like. Various coloring compositions, coloring members, and the like. According to the present invention, a method for manufacturing a pigment liquid which can further reduce the generation of foreign matter can be provided, and by using the obtained pigment dispersion liquid, the color pattern, the color filter, and the liquid crystal display device can be thresholded. Wait. I49310.doc -116-

Claims (1)

201111447 VII. Patent application scope: A method for producing a pigment dispersion liquid, which comprises the steps of uniformly dispersing a dye and a pigment in a solvent at the same time. 2. The production method according to claim 1, wherein the dye contains at least one selected from the group consisting of an azo compound, a metal complex containing an azo compound as a ligand, and a group of yam compounds. 3. The production method according to claim 1 or 2, wherein the dye contains a compound represented by the formula (1): (In the formula (1), R1 to R4 each independently represent a hydrogen atom, -R6 or an aromatic radical having a carbon number of 6 to 1 Å. The hydrogen atom contained in the aromatic hydrocarbon group may pass through a halogen atom, _R6, -OH, - 〇R6, _S03-, _S03H, S03M, -C02H, -C〇.2r6, _S〇3R6, _s〇2NHR8 or -S02N(R8)R9 are substituted, R5 is not -S03-, _s〇3H, -S03M, -C02H, -C02R6, -S〇3R6, -S02NHR8 or -S〇2N(R8)R9, the claws represent integers from 0 to 5, and when m is an integer of 2 or more, a plurality of feet! Can be the same or different. X represents a halogen atom, a represents an integer of 0 or 1, and r6 represents a saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, and the above-mentioned 149310.doc 201111447 and -CH2- contained in the hydrocarbon group may be -Ο- , -CO- or -NR6a-substituted, R6a represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R1 2 and R3 each independently represent an alkyl group having a carbon number of 10, a carbon which may have a substituent a cycloalkyl group of -3 to 30 or -Q, or R2 and R3 may be bonded to each other to form a carbon number which may have a substituent. The above-mentioned alkyl group and _Ch2 contained in the above-mentioned cyclic alkyl group _ can be via _〇_, -CO-, -NH- or -NR6a- And Q represents an aromatic hydrocarbon group having 6 to 1 carbon atoms which may have a substituent, or an aromatic heterocyclic group having 3 to 10 carbon atoms which may have a substituent, and M represents a sodium atom or a potassium atom, and the formula (1) The compound shown has a + charge number equal to the charge number). 4_ The manufacturing method of claim 1, wherein the dye and the pigment are contained in a mass ratio of dye: pigment: 叩 to 99]. 5. As requested! The manufacturing method, wherein the pigment is selected from the group consisting of cj pigment blue 15:6, Cr pigment green 36, c丄 pigment green 58, c] pigment yellow 138, c丄 pigment yellow... (7)·pigment yellow 150, c丄 pigment|xm At least one of the group consisting of ci. Pigment Red 242 and CL Pigment Red 254. ^ 6. The method of claim 1, wherein the method comprises: a method for producing a ci pigment blue 15:61-type color composition, which comprises manufacturing by The pigment dispersion obtained by the method is mixed with & selected from the group consisting of a solvent, a resin polymerizable compound, and a photopolymerization initiator. Μ 2 8 ' - a coloring pattern ' is formed by using the coloring composition obtained by the manufacturing method of the method of claim 7 149310.doc 201111447. 9. A color filter comprising the colored pattern of claim 8. A liquid crystal display device comprising the color filter of claim 9. 149310.doc 201111447 IV. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbol of the symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please reveal the best indication of the characteristics of the invention. Chemical formula: 149310.doc