TW201209102A - Pyridone azo chloride - Google Patents

Abstract

A coloring photosensitive resin composition comprises a coloring agent of dye using pyridone azo chloride as an effective ingredient, resin, photopolymerizable compound, photopolymerization initiator, and solvent. Provided is a compound represented by formula (I), wherein R1 represents hydrogen or C1-20 monovalent aliphatic hydrocarbonyl group with -CH2-, which can be substituted by -O- or -CO-; R2 represents hydrogen, cyano group, or carbamyl group; R3 represents C1-4 alkyl with hydrogen, which can be substituted by the halogen; A represents the phenyl group with at least one halogen and at least one –SO3M; M represents hydrogen or alkali metal atom.

Description

201209102 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a compound useful as a dye used in a color light-receiving sheet of a display device. [Prior Art] The dye is used for color display using reflected light or transmitted light in the field of, for example, a fiber material, a liquid crystal display device, or an ink jet. For example, in the examples of Patent Document 1, an aqueous recording liquid containing a compound represented by the following formula is described.

[Patent Document 1] Japanese Patent Laid-Open No. Hei 2 _ 15 3 9 7 7

Low, not easy to use for this purpose. The present invention is the following invention. [1] A compound represented by the formula (1):

[in the formula (1),

R1 represents a hydrogen atom or a monovalent aliphatic hydrocarbon having a carbon number of 1 to 20, 15765I.doc 201209102. The _Ch2 contained in the aliphatic hydrocarbon group may be substituted by ·〇Κ〇_; R represents a hydrogen atom, a cyano group. Or an amine group; R3 represents an alkyl group having a carbon number of 1 to 4, and a hydrogen atom contained in the alkyl group may be substituted by a halogen atom; Α represents at least one halogen atom and at least one _8 〇 3 cubits Phenyl; Μ represents a hydrogen atom or an alkali metal atom]. [2] The compound according to [1], wherein a is a group represented by the formula (1):

~~C^S〇3M

[In the formula (0, Y and γ2 each independently represent a hydrogen atom or a halogen atom, and at least one of γ1 and γ2 represents a halogen atom]. [3] A compound of [1] or [2], wherein r^_li_xi_r9 , [wherein, L丨 represents an alkanediyl group having a carbon number of 1 to 8; χΐ represents _C〇_〇_; an aliphatic hydrocarbon group having a hydrogen atom or a carbon number, and an even- [4] The compound of any one of [1] to (1), wherein χι is, [where, * represents a bond with L1] m-type dye 'which will (1) to [ 4] a compound of the formula - [0] - a coloring photosensitive resin composition, comprising: a coloring agent containing a material, a resin, a photopolymerizable compound 丨, % 尬 κ. To 157651.doc

S -4- 201209102 [Embodiment] This is a compound represented by the formula (1) (hereinafter sometimes referred to as a compound (1)).

[In the formula (1), R1 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group having a carbon number of from 1 to 20, and -CH2- contained in the aliphatic nicotine group may be substituted by -?- or -CO-. R represents no hydrogen atom, cyano group or amine sulfhydryl group. R represents an alkyl group having a carbon number of 1 to 4, and a hydrogen atom contained in the alkyl group may be substituted with a halogen atom. A represents a phenyl group having at least one halogen atom and at least one _s〇3M. Μ represents a hydrogen atom or an alkali metal atom]. Since the compound (I) has a halogen atom, the compound (1) is excellent in the bathing property with respect to an organic solvent. Further, since the compound (1) has -S03M, it is excellent in heat resistance and can suppress sublimation of the compound (I). Examples of the aliphatic hydrocarbon group having a monovalent value of R1 include a methyl group, an ethyl group, a propyl group, an isobutyl group, a butyl group, a tert-butyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a decyl group, and the like. . The -CH2- contained in the above aliphatic hydrocarbon group may be substituted by -〇- or -CO-. Examples of such a group include -C2H4_〇C6Hi2, -C2arCO-C6H12, -C2H4-0-C0-0-C6H12, -C2H4-0-C2H4-C0-C6H12, and the like. 157651.doc 201209102 2 2 is Π-1"9. If R1 is -1LxLr9, there is a tendency that the solubility of δ9 of the present invention for an organic solvent is improved, and it is preferable. :: A hydrogen atom or an aliphatic hydrocarbon group having a carbon number of valence, which may be substituted by _〇· or _c〇. As the aliphatic hydrocarbon group, it can be listed as the aliphatic hydrocarbon group of the monovalent value of the valence of 1*20. The monovalent aliphatic nicotinyl group substituted may be, for example, R being a hydrogen atom, a mercapto group or an ethyl group. L1 and L2 are each independently alkanediyl having a carbon number of Η, 1, an ethyl group, a decyl group, a propyl group, a butyl group: a dialkyl group, a butane-1,3-diyl group, and a 栌! ς a 戊 pentane, a group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane q,8-diyl group and the like. X1 and X2 are · ί:0·0 "χ1 is particularly good for *孤〇_(* indicates the connection with L2

key). If X1 is * _C0-0_, the target is ng > A, and the compound of the present invention is produced in comparison with the R or the like of the prefecture, and for example, the formula of the formula can be cited. Here, as ax1_l2_x2r10, for example, a group represented by σ-υ~ (f-2〇) can be cited. Preferably, it is preferably a formula (4), a formula (f_5), a formula (f_6), a formula (4), a formula (4)), a formula (4)), a second (fM), a formula (f_17), a formula (M8), and a formula (f 24). The base represented by is represented by the formula (f-2), the formula (f-6), the formula (Μ0), the formula (f l4), the formula ((«4), and more preferably the formula ( M4) and (10) the basis of the heart. 157651.doc

S 201209102

I57651.doc 201209102

(f-25)

(f-22) (f-24) R is a hydrogen atom, a cyano group, or an amine fluorenyl group. Among them, the cyano group is preferred in terms of easy availability of the raw material. Examples of the alkyl group having a carbon number of i3 to R4 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. The hydrogen atom contained in the alkyl group may be substituted by a functional atom. Examples of the γ atom include a fluorine atom, a gas atom, and a desert atom. The alkyl group in which the number of carbon atoms of the hydrogen atom substituted by the dentate atom is arsenic is, for example, a trifluoromethyl group or a pentafluoroethyl group. R is preferably a methyl group and a tri-I methyl group, more preferably a methyl group. VIII is a sulphur atom, and at least one benzene is a sulphur atom. Examples of the dentate atom include a gas atom, a gas atom, an atomic earth, a sub-element, etc., because the compound (1) has a halogen atom, the compound (1) The solubility of the solvent is excellent. Among them, the solubility is more preferable, and it is preferably a chlorine atom, more preferably two chlorine atoms. The beryllium is a hydrogen atom or a metal atom is used as a metal test. I5765J.doc 201209102 Sodium, potassium, etc. As a hydrazine, preferably a hydrogen atom and a sodium atom, more preferably a phenyl group in a hydrogen hydrazine, in addition to having a (iv) atom and a pi-, may also have a carbon number of The base of the hospital, the oxy group having a carbon number of W, the alkyl group having a carbon number of hydrazine, a hydroxyl group, a cyano group or a nitro group. Examples of the alkyl group having a carbon number of 1 to 8 include a mercapto group. a linear alkyl group such as ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl or n-octyl; isopropyl, isobutyl, t-butyl, isopentyl, anthracene _Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, ethylethylbutyl, 2-ethylbutyl, 1-decylhexyl , 2-decylhexyl, 3-hydrazinohexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, hydrazine-propyl Butyl, 1-(1-methylethyl)butyl, anthraquinone-hydrazinoethyl)-2-methylpropyl, 1-methylheptyl, 2-decylheptyl, 3-hydrazine Heptylheptyl, 4-decylheptyl, 5-methylheptyl, 6-fluorenylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4·ethylhexyl, 1 - n-propylpentyl, 2-propylpentyl, 1-(1-decylethyl)pentyl, 1-butylbutyl, 1-butyl-2-mercaptobutyl, 1-butyl -3-mercaptobutyl, 1-(1,1-dimethylethyl)butylbutyl, tert-butyl, 1,1-dimercaptopropyl, 1,1-dimethylbutyl 1,2-dimercaptobutyl, 1,3-dimercaptobutyl, 2,3-dimethylbutyl, 1-ethyl-2-mercaptopropyl, 1,1-dimethyl Pentyl, 1,2-dimethylpentyl, 1,3-dioxylpentyl, 1,4-dimethylpentyl, 2,2-didecylpentyl, 2,3-didecyl Pentyl, 2,4-didecylpentyl, 3,3-didecylpentyl, 3,4-dimethylpentyl, 1-ethyl-1-indenylbutyl, 1-ethyl- 2-mercaptobutyl, 1-ethyl-3-methyl Butyl, 2-ethyl-1-methylbutyl, 2-ethyl 157651.doc -9· 201209102 -3--3-mercaptobutyl, 1, bisdimethylhexyl, 1,2-dimethyl Hexyl, 1,3-dimethylhexyl, 1,4-dimethylhexyl, 1,5-dimethylhexyl, 2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4 - dimethylhexyl, 2,5-didecylhexyl, 3,3-dimercaptohexyl, 3,4-dimercaptohexyl, 3,5-dimethylhexyl, 4,4-dimethylhexyl 4,5-Dimethylhexyl, 1-ethyl-2-methylpentyl, 1-ethyl-3-indolylpentyl, 1-ethyl-4-mercaptopentyl '2-ethyl -1-methylpentyl, 2-ethyl-2-mercaptopentyl, 2-ethyl-3-indolylpentyl, 2-ethyl-4-mercaptopentyl, 3-ethyl-1 -methylpentyl, 3-ethyl-2-mercaptopentyl, 3-ethyl-3-indolylpentyl, 3-ethyl-4-methylpentyl, 1-propyl-1-methyl Butyl, 1-propyl-2-methylbutyl, 1-propyl-3-mercaptobutyl, 1-(1-methylethyl)methylbutyl, 1-(1-indenyl) Branches such as ethyl)-2-mercaptobutyl, 1-(1-decylethyl)_3_decylbutyl, 1,1-diethylbutyl, 1,2-diethylbutyl Alkyl group. Examples of the alkoxy group having a carbon number of 1 to 8 include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and a 2-ethyl group. Hexyloxy group and the like. Examples of the oxyalkyl group having a slave number of 2 to 8 include, for example, a methoxyindenyl group, a decyloxyethyl group, a methoxypropyl group, a nonyloxybutyl group, a methoxypentyl group, and 1- Ethoxypropyl, 2-ethoxypropyl, ethoxylated <methylethyl, decyl-2-ethoxyethyl, decylethoxy)propyl, 2_(ι methyl Oxy)propyl, phenyl(1-fluorenylethoxy)]-methylethyl, 2-mercaptoethoxy)-1-mercaptoethyl, 3-ethoxypropyl, and the like. As A, a group represented by the formula (1) is preferred. 157651.doc 201209102

f Formula (1) t, Y丨 and γ2 are independent of each other and at least - represent a prime atom or a samarium atom, in the formula represented by the formula (1), preferably in the group to + -^ &lt; It is selected from the group consisting of Υ1 and Υ2: η 'is a chaotic atom, more preferably Υ1 and Υ2 are gas atoms.笪 匕 物 物 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( The number of the formula of the above-exemplified group is described. For example, the compound is a compound represented by the following formula (6).

157651.doc 201209102 [Table i] Compound R 1 R2 R3 R4 R5 R 6 R7 R8 1-1 f-1 CN ch3 H Cl s o3h H Cl 1-2 f-3 CN ch3 so3h H Cl Cl H 1-3 f -4 CN ch3 H so3h HH Cl 1-4 f-5 CN ch3 H so3h Cl HH 1-5 f-6 CN ch3 H Cl s o3h H Cl 1-6 f-7 CN ch3 so3h H Cl Cl H 1-7 F-8 CN ch3 H so3h HH Cl 1-8 f-9 CN ch3 H so3h Cl HH 1-9 f-10 CN ch3 H Cl s o3h H Cl I- 1 0 f-11 CN ch3 s o3h H Cl Cl H 1-1 1 f-12 CN ch3 H so3h HH Cl 1-12 f-13 CN ch3 H so3h Cl HH 1-13 f-15 CN ch3 H Cl s o3h H Cl 1-14 f-16 CN ch3 so3h H Cl Cl H 1-15 f-17 CN ch3 H so3h HH Cl 1-16 f-18 CN ch3 H so3h Cl HH 1-17 f-19 CN ch3 H Cl s o3h H Cl 1-18 f-20 CN ch3 s o3h H Cl Cl H 1-19 f-22 CN ch3 H so3h HH Cl 1-2 0 f-23 CN ch3 H so3h Cl HH 1-2 1 f-25 CN ch3 so3h H Cl Cl H 1-2 2 f-1 CN cf3 ch3 Cl S 03H H Cl 1-2 3 f-3 H ch3 so3h ogh3 Cl Cl H 1-2 4 f-4 conh2 cf3 H so3h CH20CH3 H Cl 1-2 5 f-5 CN ch3 H so3h Cl OH H 1-2 6 f-6 H cf3 H Cl s o3h N〇2 Cl 1-2 7 f-7 conh2 ch3 so3h F Cl Cl H 1-2 8 f-8 CN cf3 B r so3h HH Cl 1-2 9 F-9 H ch3 B r so3h Cl HH 1-3 0 f-10 conh2 cf3 B r Cl s o3h H Cl 1-3 1 f-11 CN ch3 so3h B r Cl Cl H 1-3 2 f-12 H c F 3 H so3h B r H Cl 1-3 3 f-13 conh2 ch3 H so3h Cl B r H 1-3 4 f-15 CN cf3 H Cl s o3h B r Cl 1-3 5 f-16 H ch3 so3h H Cl Cl B r 157651.doc •12- s 201209102 1-3 6 f-17 conh2 cf3 H so3h HB r Cl 1-3 7 f-18 CN ch3 H so3h Cl HB r 1-3 8 f-19 H cf3 ch3 Cl s o3h H Cl 1-3 9 f-20 C0NH2 ch3 so3h och3 Cl Cl H 1-4 0 f-22 CN cf3 H so3h CH20CH3 H Cl 1-4 1 f-23 H ch3 H s o3h Cl OH H 1- 4 2 f-25 CN ch3 s o3h F Cl Cl H 1-4 3 f-2 CN ch3 H Cl s o3h HC 1 1-44 f-2 CN ch3 s o3h H Cl Cl H 1-4 5 f-2 CN Ch3 H so3h HH Cl 1-4 6 f-2 CN ch3 H so3h Cl HH 1-4 7 f-2 CN c f3 s o3h och3 Cl Cl H 1-4 8 f-2 conh2 ch3 H so3h ch2och3 H Cl 1- 4 9 f-2 H cf3 H so3h Cl OH H 1-5 0 f-2 conh2 ch3 s o3h F Cl Cl H 1-5 1 f-2 CN ch3 B r so3h HH Cl 1-5 2 f-2 CN cf3 B r Cl s o3h H Cl 1-5 3 f-2 conh2 cf3 H so3h B r H Cl 1-5 4 f-2 CN cf3 H so3h Cl B r H 1-5 5 f-2 H ch3 H Cl s o3h B r Cl 1-5 6 f- 2 CN cf3 H so3h HB r Cl 1-5 7 f-2 H ch3 H so3h C 1 HB r 1-5 8 f-14 CN ch3 H Cl so3h H Cl 1-5 9 f-14 CN ch3 so3h H Cl Cl H 1-6 0 f-14 CN ch3 H so3h HH Cl 1-6 1 f-14 CN ch3 H so3h Cl HH 1-6 2 f-14 CN ch3 ch3 Cl so3h H Cl 1-6 3 f-14 CN ch3 B r so3h HH Cl 1-6 4 f-14 CN ch3 B rs o3h Cl HH 1-6 5 f-14 CN cf3 B r Cl so3h H Cl 1-6 6 f-14 H ch3 so3h B r Cl Cl H 1 -6 7 f-14 conh2 cf3 H so3h B r H Cl 1-6 8 f-14 CN cf3 H s o3h Cl B r H 1-6 9 f-14 H ch3 H Cl s o3h B r Cl 13- 157651. Doc 201209102 1-7 0 f-14 conh2 cf3 so3h H Cl Cl B r 1-7 1 f-14 CN c f3 H s o3h HB r Cl 1-7 2 f-14 H ch3 H s o3h Cl HB r 1- 7 3 f-21 CN ch3 H Cl s o3h H Cl 1-7 4 f-21 CN ch3 so3h H Cl Cl H 1-7 5 f-21 CN ch3 H s o3h HH Cl 1-7 6 f-21 CN ch3 H so3h Cl HH 1-7 7 f-21 CN ch3 ch3 Cl s o3h H Cl 1-7 8 f-21 CN cf3 so3h och3 Cl Cl H 1-7 9 f-21 C0NH2 ch3 H s o3h CH20CH3 H Cl 1- 8 0 f-21 H c f3 H so3h Cl OH H 1-8 1 f-21 CN ch3 H Cl s o3h N02 Cl 1-8 2 f-21 C0NH2 ch3 so3h F Cl Cl H 1-8 3 f-21 CN CF 3 H So3h Cl B r H 1-8 4 f-21 H ch3 H Cl s o3h B r Cl 1-8 5 f-21 C0NH2 c f3 so3h H Cl Cl B r 1-8 6 f-21 CN c f3 H s o3h HB r Cl 1-8 7 f-21 H ch3 H s o3h Cl HB r 1-8 8 f-24 CN ch3 H Cl s o3h H Cl 1-8 9 f-24 CN ch3 s o3h H Cl Cl H 1- 9 0 f-24 CN ch3 H s o3h HH Cl 1-9 1 f-24 CN ch3 H s o3h C 1 HH 1-9 2 f-24 CN ch3 ch3 Cl s o3h H Cl 1-9 3 f-24 CN c f3 so3h och3 Cl Cl H 1-9 4 f-24 conh2 ch3 H so3h CH20CH3 H Cl 1-9 5 f-24 H cf3 H s o3h Cl OH H 1-9 6 f-24 CN ch3 H Cl so3h no2 Cl 1-9 7 f-24 conh2 ch3 so3h F Cl Cl H 1-9 8 f-24 CN ch3 B rs o3h HH Cl 1-9 9 f-24 CN ch3 B rs o3h Cl HH 1-10 0 f-24 CN Cf3 B r Cl s o3h H Cl 1-10 1 f-24 H ch3 so3h B r Cl Cl H 1-10 2 f-24 conh2 cf3 H so3h B r H Cl Among them, preferred is compound (1-1)~ Compound (1-2 1), compound (1-43)-compound (1-46), compound (1-58) to compound (1-61), compound (1-73) to compound (1-76) and Compound (1-88) to compound (1-91) 'more preferably compound (1-43) to compound (1-44), compound (1-5 8), Compound (1-59), compound-14-157651.doc 201209102 (1-73)~ compound (1_74) and compound (4))~ compound (i 89), and more preferably compound (1_58) and compound (us) . When the right compound (I) is such a compound, the solubility in an organic solvent tends to be high in the strength of the compound. By the Japanese Patent Special Fair 7 German nickname. The diazonium salt represented by the formula (8) and the pyridinium compound represented by the formula (4)) are produced by diazo coupling. The diazonium sulphate represented by the formula (a2) is an amine of the formula 丨 & & & & & & & & & & & & & 胺 胺 胺 胺 胺 胺 胺 胺 胺 胺 胺 胺 胺Obtained by diazotization.

Ο1] By using, for example, nitrous acid, sulphate a-nh2 (al) [formula (al), formula (a2), and formula (a3), R1 to R3 and a each have the same meaning as described above. A1 represents an inorganic anion or an organic anion] The inorganic anion is exemplified by a fluoride ion, a vaporized ion, a bromide ion, an iodine ion or the like as the organic anion, for example. The compound ion, the perchloric acid ion, and the hypochlorous acid may be exemplified by ch3coo·, Phcocr &quot;T, and it is preferable that the vaporization is earlier than the potassium, bromide ion, and ch3coct. By comparing the ratio of the diazonium salt of the formula (a2) to the ratio of the diazonium salt represented by the formula (a3). The compound of the present invention can be produced by subjecting the compound of the formula I to diazo coupling in an aqueous solvent. The reaction temperature is ~5C~6 (TC, more preferably 0°C~30°c. 157651.doc 201209102 The reaction time is preferably from 1 hour to 12 hours, more preferably from 1 hour to 4 hours. Examples of the solvent include N-methylpyrrolidone, etc. In the compound of the present invention, R1 is -LLxLr9, and oxime is * _〇c〇 compound (Ib) (* indicates a bonding position with L1), that is, A method for producing a compound represented by the formula (hereinafter sometimes referred to as "compound") will be described.

[In the formula (10), ', V, A and the same meaning as described above> The heavy (tetra) salt represented by the formula (a2) and the &lt; represented by the formula (b3) are obtained by the same method as described above. (4) The compound is subjected to diazo coupling, and an azo compound represented by the formula (b4) can be produced.

R, A and L1 respectively represent the same meanings as described above in the formulae (b3) and (b4), and the meaning of the meaning of r2, and the meaning of the azo compound, and Z is a gas atom, and the compound (Ib) can be obtained. Then, by reacting R'CO-Z1 represented by the formula (b4) (wherein R9 represents the same or a bromine atom as above) in the presence of an organic solvent 157651.doc

S-16-201209102 The reaction temperature is preferably 3 (TC~180t, more preferably 5(rc~12(rc. The reaction time is preferably 1 hour to 12 hours, more preferably! hours to 4 hours.) Examples of the solvent include a hydrocarbon solvent such as toluene or xylene, a hydrocarbon solvent such as chlorobenzene, diphenylbenzene or chloroform, a nitrohydrocarbon solvent such as nitrobenzene, a ketone solvent such as methyl isobutyl ketone, and a methyl group H (IV). The amount of the V-co-z1 to be used is usually 8 mol or less per mol of the azo compound i mol represented by the formula (b4), and preferably 4 mol or less. In the case of the compound of the present invention, R^_Ll〇cLR9, and _〇_c〇_ of the compound (1) (wherein the bonding position of 4 and L1), that is, the compound represented by the formula (10) (hereinafter, sometimes The manufacturing method of the case of the "compound (lc)") will be described.

[In the formula (10), ..., ..., ^ is not the same as the above meaning] By using the same method as described above, the diazo salt represented by the formula (a2) is represented by the formula (e3) The azo compound represented by the formula (c4) can be produced by diazo coupling with a compound.

15765I.doc 201209102 [In the formulas (c3) and (C4), the meanings of R2 and R3] A and L1 respectively denote the same as above, and 9', by making the azo compound represented by the formula (4) and R, 0H ( Straight, R represents the same meaning as above, and is reacted in the presence of an organic solvent to obtain a compound (10). The reaction temperature is preferably 3 (rc ~ war, more preferably thief ~ Cong. The reaction time is preferably A1 hour ~ 12 hours 'better" for hours ~ 4 hours. As a result of the organic _, can be (four) and The solvent which is the same as the one used in the reaction of the azo compound represented by the formula (10). The amount used is 1 mol or more with respect to the azo compound i represented by the formula (e4). Below the ear, it is preferably at least 4 moles of J mole or more. 'In the reaction, the reaction is carried out smoothly, and it is more preferable to add an acidic catalyst. Examples of the acidic catalyst include inorganic acids such as sulfuric acid and hydrochloric acid. The amount of the catalyst used is arbitrary, but it is preferably 〇.01 〜4 mol [preferably 0.8 to 2 mol) relative to 丨莫耳r9_〇h. The reaction mixture is obtained as a target compound. The method of the compound of the present invention is not particularly limited, and various known methods can be employed. For example, the counter compound can be mixed with an acid (for example, 'acetic acid or the like) and water, and the above-mentioned acid is precipitated. After preparing the aqueous acid solution in advance, the reaction mixture is not added to the above water. In the liquid, the temperature at the time of adding the reaction mixture is usually 10 C or more and 50. (: The following is preferably 2 〇〇 c or more and 5 〇〇 c or less is more preferably 2 〇. 〇 is 30 ° C or less. Further, the reaction is carried out. After the mixture is added to the aqueous acid solution, 157651.doc •18·S, 201209102 is preferably stirred at the same temperature for about 5 to 2 hours. The crystals to be filtered are preferably washed with water or the like, followed by drying. Further, if necessary, it may be further purified by a known method such as recrystallization. The compound of the present invention is useful as a dye. The dye of the present invention is a compound of the present invention as an active ingredient. The dye of the present invention is an organic solvent. In particular, it is useful as a dye used for a color filter of a display device such as a liquid crystal display device. The colored photosensitive resin composition of the present invention comprises a coloring agent containing the dye of the present invention (hereinafter, It may be called "colorant (A)"), resin (B), photopolymerizable compound (C), photopolymerization initiator (D), and solvent (E). Colorant (A) contains the present invention. dye Further, it may further contain a pigment and/or a dye different from the dye of the present invention. As a dye different from the dye of the present invention, it may be exemplified by a color index (Colour IndexK The Society of Dyers and c〇1〇urists). It is a Solvent, Acid, Basic, Reactive, Direct, Disperse, or Vat dye, etc. More specifically, the following Color index (CI.) number of dyes, but not limited to these: CI, solvent yellow 25, 79, 81, 82, 83, 89; CI acid yellow 7, 23, 25, 42, 65, 76; CI Reaction Yellow 2, 76, 116; CI Direct Yellow 4, 28, 44, 86, 132; CI Disperse Yellow 54, 76; 157651.doc • 19- 201209102 CI Solvent Tan 41, 54, 56, 99; CI Acid Orange 56, 74, 95, 1〇8, 149, 162; CI reaction orange 16; CI direct dial 26; CI solvent red 24, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132 , 160, 218; CI acid red 73, 91, 92, 97, 138, 151, 211, 274, 289; CI acid purple 102; CI solvent green 1, 5 C.I. Acid Green 3, 5, 9, 25, 28; C · I. Green 1; C.I. Green 1 and so on. Examples of the pigments include organic pigments or inorganic pigments used in the pigment dispersion reaction (4). Examples of the inorganic pigment include metal compounds such as a metal oxide or a metal salt, and specific examples thereof include metals such as iron, aluminum, cadmium, lead, copper, titanium 'magnesium, chromium, zinc, and antimony. Oxide or composite metal oxide. Further, as the organic pigment and the inorganic pigment, specifically, a Colour Index (The s〇ciety 〇f (1) _

Colourists publishes compounds classified as pigments. More specifically, the following color index (1) 丄) number of pigments may be mentioned, but it is not limited thereto. C.I. Pigment Yellow 20, 24, 3 Bu 53, 83, 86, 93, 94, 109, 110, (1), 125, 137, 138, 139, 147, 148, 15〇, 153, 154,

157651.doc -20- S 201209102 166, 173 and 180; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64 '65 and 71; CI·Pigment Red 9 , .97, 1〇5, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 215, 216, 224, 242, 254, 255 and 264; CI·Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38; CI Pigment Green 7, 1, 〇, 15, 25, 36, 47 and 58 and so on. The content of the colorant (A) is preferably from 5 to 60% by mass based on the solid content of the colored photosensitive resin composition. Here, the solid content component is a total of components other than the solvent in the coloring photosensitive resin composition. The content of the dye of the present invention contained in the colorant (A) is preferably from 3 to 丨〇〇% by mass. The dye of the present invention and the dye and pigment different from the dye of the present invention may be used alone or in combination of two or more. The resin (B) is not particularly limited, and any resin can be used. The resin is preferably an alkali-soluble resin, and more preferably a resin comprising a structural unit derived from (meth)acrylic acid. Here, (meth)acrylic acid means acrylic acid and/or methyl acrylic acid. Specific examples of the resin (B) include mercaptoacrylic acid/methacrylic acid vinegar copolymer, methyl acrylic acid/methyl propyl acetophenone styrene copolymer, and methacrylic acid/methyl group. Propylene glycol vinegar 1 propyl acetoacetate isobornyl ester copolymer, methyl propyl benzoic acid / styrene / methacrylic acid f ggt / N_ phenyl maleimide copolymer, f-based acrylic / styrene / Glycidyl methacrylate copolymer 15765J.doc • 21 · 201209102 and so on. The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably from 5,000 to 35,000, more preferably from 6 to 3 Torr. The acid value of the resin (B) is preferably from 5 Å to 15 Å, more preferably from 6 Å to 135 Å. The content of the resin (B) is usually 7 to 65 mass%, preferably 13 to 6 mass%, based on the solid content of the colored photosensitive resin composition. The photopolymerizable compound (C) is a compound which can be polymerized by using an active radical, an acid, or the like which is generated from a photopolymerization initiator (D) by light irradiation, and is not particularly limited. A compound of a carbon-carbon unsaturated bond or the like. The photopolymerizable compound (c) is preferably a photopolymerizable compound having three or more polymerizable groups. Examples of the photopolymerizable compound having three or more polymerizable groups include, for example, pentaerythritol tetrapropionic acid S, pentaerythritol tetramethacrylate, and schizophrenia m β-limopentitol pentapropan acid. Vinegar, dipentaerythritol, methane propylene, 夂酉曰-pentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate (IV). These photopolymerizable compounds (C) may be used singly or in combination of two or more. The content of the first polymerizable compound (C) is preferably from 5 to 65 mass%, more preferably the mass of the pigment (1), based on the solid content of the colored photosensitive resin composition. A The photopolymerization initiator (D) may, for example, be an active agent or an acid generator. The active white radical is produced by irradiating light to the active radical. Examples of the living radical generating agent include a phenone compound and a thioxanthone compound, and = as the acetophenone compound, and examples thereof include a compound and a fatty compound. For example, the milking mouth can be exemplified by 2_methyl_2_?

S •22- 201209102 -1-(4-Methylamine-glycosylphenyl)propan-1-one, 2-carbyl-2-methyl-ι-benzene-propan-1-one, benzoin Methyl ketal, 2-hydroxy-2-methylethoxy) benzyl]propan-1-yl, 1-cyclohexylphenyl hydrazine, and the like. As the above thioxanthone compound, for example, 2-isopropylisoxanone, 4-isopropylthioxanthone, 2,4-diethylthiazepine_, 2,4•digas can be cited. Xanthone, 1-chloro-4-propoxythiaxanone, and the like. Examples of the compound of the above-mentioned 31-well can be exemplified by 2,4 _bis(r:chloromethyl)·6-(4-methoxyphenyl)-1,3,5_three tillage, 2,4_double (tri-gas methyl) _6-(4_ methoxyoxynaphthyl)-1,3,5-three tillage, 2,4-bis(trimethylmethyl)_6_('methoxybenzene,-bis(di) Methyl)-6-[2-(5-methylfuranyl)-1,3,5-three wells)vinyl]-1,3,5-three tillage, 2,4_double (three Chloromethyl)_6_[2_(furan-2-yl)ethenyl]-1,3,5-three wells, 2,4-bis(trichloroindenyl)_6_[2_(4_diethylamino) winter Methylphenyl)ethylcarbyl]·1,3,5-three wells, 2,4_bis(trichloromethyl)_6_[2_(3,4-dimethoxyphenyl)ethenyl]-1 , 3, 5 - Mitsui and so on. Examples of the ruthenium compound include a ruthenium-based fluorene-based compound, and specific examples thereof include Ν_benzylideneoxy-indole 4-phenylsulfonylphenyl)butan-1-one-2 -imine, fluorenyl-benzoyloxy-4-alkan-1-one-2-imine, fluorenyl-ethoxycarbonyl)-9-oxazol-3-yl]ethane-1-imine, - (4-phenylsulfonylphenyl)octyl-ethyl-6-(2-methylphenylhydrazone N-acetoxyl-l-[9-ethyl-6-{2-methyl-4 -(3,3-dimercapto-24-prepared) 2,4 one gas cyclopentyl decyloxy)phenylhydrazinyl 9H-carbazol-3-yl]ethane-1-imine, etc. As a living radical generator, for example, 2,4'6-trimethylbenzyl can also be used: phenylphosphine oxide, 2,2,·bis(o-phenyl)-4,4, from tetraphenylene Based on him, 1〇_butyl-2·gas.丫(10), 2-ethyl onion, diphenyl 157651.doc -23- 201209102 9' 10-phenanthrenequinone, camphorquinone, acetophenone oxime ester And a ferrocene-diethyl ketone, etc. As the above-mentioned acid generator, for example, 4-hydroxyphenyl bis-f-p-p-toluene "I salt, 4 · mercapto phenyl bisphosphonate Salt, heart ethoxylated phenyl-indoyl hydrazine Acid salt, 4-acetoxyphenyl-methyl-dibenzophenone oxime V, fluoroantimonate, triphenylsulfonium p-benzenesulfonate, triphenylsulfonium hexahydrate, two a phenyl hydrazine p-toluene acid salt, a diphenyl hexahydrate salt, and the like, a benzoic acid vinegar, a benzoin, a benzoic acid ester, etc., the photopolymerization initiator (D) It is also possible to use two or more kinds in combination. The total amount of the photopolymerization initiator (D) relative to the resin (B) and the photopolymerizable compound (C) is preferably 〇 〇 〇 〇 / More preferably, it is 1 to 20% by mass. If the content of the photopolymerization initiator is in the above-mentioned range, the sensitivity is shortened and the productivity is improved, which is preferable. As a solvent (Ε) For example, the chewing aromatic hydrocarbons, the ketones other than the above, the alcohols, the esters, the amines, and the like. Examples of the ethers include four-rolled Tiannan, tetraterpene pyran, and , 4_ 一烧, Ethyl alcohol monoterpene, B-alcohol setting &gt; ^ G-alcohol soap ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol mono_^-ethyl alcohol monoethyl , diethylene glycol monobutyl ether, diethylene glycol dimethyl _ ^ ^ - ethyl alcohol diethyl ether, diethylene glycol decyl ethyl ether, diethylene 2) 3⁄43⁄4, diethylene glycol Butanol, propylene glycol monoterpene ether acetate, C--: flat 0 ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl hydrazine, ethylene glycol monoethyl ether acetate 157651.doc • 24- Examples of 201209102 include: 4-methyl-2-pentanone ester, diethylene glycol monoethyl ether acetate, and the above-mentioned aromatic hydrocarbons, for example, homotrimethane. Examples of the ketone include diethylene glycol monobutyl ether acetate such as 3-heptanone, 4-heptanone, cyclopentanone or cyclohexanone. Examples thereof include benzene, toluene, xylene, acetone, 2-butanone, 2-heptanyl, and 4-hydroxy-4-mercapto-2-pentanone. Examples thereof include methanol, ethanol, and propanol. Butanol, hexanol, cyclohexanol, ethylene glycol, glycerin, etc. As the above-mentioned esters, for example, ethyl acetate, n-butyl acetate, aceto-isobutyl S-hydrazine, amyl formate, isoamyl acetate, isobutyl acetate, butyl s-propionate, isopropyl butyrate Ester, ethyl butyrate, butyl butyrate, alkyl esters, chyloside, ethyl lactate, butyl lactate, methyl methoxyacetate, methoxy ethoxylated 曰 曰 methoxy Butyl acetate, ethoxyacetic acid, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, decyl 3-ethoxypropionate, 3 -ethyl ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionate, 2-methoxypropionic propylene vinegar, 2-ethoxypropionic acid , 2_Ethyl ethoxypropionate, methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-mercaptopropionate, decyl pyruvate, ethyl pyruvate , propyl pyruvate, methyl acetate methyl acetate, ethyl acetate ethyl acetate 'acetic acid 3-methoxybutyl ester, acetic acid 3-mercapto-3-methoxy butyl vinegar, γ-butane vinegar and the like. Examples of the above guanamines include ν, ν-dimethylformamide, ν, ν-dimethylacetamide, Ν-methylpyrrolidone, and the like. These solvents may be used singly or in combination of two or more. The content of the solvent in the colored photosensitive resin composition is preferably from 7 Å to 95% by mass based on the photosensitive resin composition of 157651.doc -25 - 201209102. /〇, 争杜 Also -1 main V 3~9 〇 Temporary 'Tian %. The colored photosensitive resin composition of the present invention may optionally contain various additives such as an agent, a filler, another polymer compound, an adhesion promoter, an antioxidant, an ultraviolet absorber, a light stabilizer, and a chain transfer agent. The compounds of the invention are useful as dyes. Since the solubility in an organic solvent is high, it is particularly useful as a dye used for a color filter of a display device such as a liquid crystal display device. Further, the color-sensitive photosensitive resin composition containing the compound of the present invention can be used in a known display device for a part including a color filter as a constituent member (for example, a known liquid crystal display device, organic EL (eleCtr) Various devices related to colored images, such as 〇luminescence 'electroluminescence devices, and solid-state imaging devices. EXAMPLES Next, the present invention will be specifically described by way of examples. In the examples and comparative examples, unless otherwise stated, the % and the parts of the content or the amount used are based on the mass basis. In the following examples, the structure of the compound was confirmed by NMR (Nuclear Magnetic Resonance) (JMMECA 5®; manufactured by Nippon Denshi Co., Ltd.). Example 1 After adding 254 parts of water to 25.3 parts of 2,5-dichloroaminobenzenesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 4 parts of sodium hydroxide was added to dissolve it. Under cooling, add 2 丨 7 parts of sodium nitrite solution, then slowly 157651.doc 26

S 201209102 66.9 parts of 35% hydrochloric acid was added thereto, dissolved and stirred for 3 hours. The ice bath was cooled, and a solution obtained by dissolving 19.7 parts of amidoxime sulfonic acid in 197 parts of water was added to obtain a suspension containing a diazonium salt. On the other hand, '173 parts of ethyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), decyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) 15 parts, 142 parts of piperidine, and DL-1-amino group- 125 parts of 2-propanol (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 95 ° C for 24 hours. After the reaction solution was cooled at room temperature, it was added to 2000 parts of water and 35% hydrochloric acid. The mixture was stirred at room temperature for 1 hour, and the precipitated crystal was taken as a residue for suction filtration, followed by drying to obtain 125 parts of the compound represented by the formula (d1).

&lt;Zhengding of the compound represented by the formula (d 1)&gt; ^-NMR: 1.04 (3H), 2.23 (3H), 3.88 (2H), 3.95 (1H), 5.64 ΠΗ), 8.04 (1H), 8.04 (1H) 驴 , 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 〇 It took about 5 minutes to pump a suspension containing the above-mentioned diazonium salt by a pump. After completion of the dropwise addition, the mixture was further stirred for 30 minutes, whereby a yellow suspension was obtained. Stir, hour. The yellow solid obtained by filtration was dried under reduced pressure at 6 (TC) to afford 30.0 parts of the compound represented by formula (d2). The structure was confirmed by 1h_nmr. 15765l.doc -27- 201209102

Na〇3S~H Cl &lt;Identification of the compound represented by the formula (d2)&gt; Ή-NMR: 1.08 (3H), 2.55 (3H), 3.81 (2H), 3.95 (1H), 4.81 (1H), 7.72 (1H), 7.95 (1H), 14.76 (1H) To add 3.18 parts of the compound represented by the formula (d3) to 3.06 parts of the compound represented by the formula (d2). In the same solvent, it was stirred for 3 hours. After the completion of the reaction, it was added to water to obtain 2.01 part of the compound represented by the formula (158). The structure was identified by iH-NMR domain.

&lt;Identification of a compound represented by formula (1-58) &gt; H-NMR: 1.1〇(3H), 1.22 (3H), 2.49 (2H), 2.49 (2H), 2.56 (3H), 3.96 (2H ), 4.25 (2H), 5.13 (1H), 7.75 (1H), 7.97 (1H), 11.88 (1H), 14.79 (1H) Dissolve the obtained compound represented by formula (1_58) 〇.1〇g In the diterpene amide, the volume is 25 〇 cm 3 , and 2 cm 3 of it is diluted with ethyl lactate to make a volume of 100 cm 3 (concentration: 〇0080 g / L), using UV 157651.doc

S 201209102 Spectrophotometer (V-650DS; manufactured by Sakamoto Seiko Co., Ltd.) (quartz tank, optical path length: 1 cm) 'Measure the absorption spectrum. The compound λ_χ = 432 nm ' exhibits a bright yellow 'Mole absorbance coefficient which shows a higher value of 38 。. Example 2 To a solution of 3.02 parts of the compound represented by the formula (d2), 3.20 parts of the compound represented by the formula (d4) was added, and the mixture was stirred at 7 ° C for 3 hours in a solvent of N-methylpyrrolidone. After completion of the reaction, it was added to water to obtain 1.96 parts of the compound represented by the formula οι. The structure was confirmed by W-NMR.

&lt;Identification of the compound represented by the formula (1-88)&gt; 1H-NMR: 0.60-1.60 (17H), 2.11 (1H), 2·55 (3H), 4.25 (2H), 5.13 (1H), 7.77 (1H), 7.95 (1H), 11.77 (1H), 14.75 (1H) The obtained compound o.io g represented by formula (1-88) was dissolved in dimethylformamide. The volume was 250 cm3 '2 cm3 was diluted with ethyl acetate to make the volume 100 cm3 (concentration: 0.0080 g/L), using an ultraviolet-visible spectrophotometer (V-650DS; manufactured by Sakamoto Seiko Co., Ltd.) (Quartz cell 'optical path length: 1 cm), the absorption spectrum was measured. The compound λη^χ = 433 nm' exhibited a vivid yellow color, and the molar absorption coefficient exhibited a higher value of 38 。. Comparative Example 1 157651.doc -29-201209102 In Example 1, '2-aminoterephthalic acid was used instead of 5-nitro-o-amine benzoic acid, and the compound represented by formula (el) was used instead of A compound represented by the formula (X) was obtained in the same manner as in Example 1 except for the compound represented by the formula (d).

[Evaluation of Solubility] The propylene glycol monomethyl ether acetate (hereinafter, abbreviated as PGMEA (Pr〇pylene §1 〇1 monomethyl ether acetate)) obtained in Examples 丨 and Comparative Example was determined in the following manner. Monomethyl ether (hereinafter, abbreviated as PGME (Propylene glyc〇1 m_methyl ethe〇), lactic acid (hereinafter, abbreviated as EL (ethyl lactate)) N-methylpyrrolidone (hereinafter, abbreviated as NMP (N-methylpyrr〇iid) The solubility in 〇ne)). In a 50 mL sample tube, the compound was mixed with the above solvent in the following ratios. Then the sample tube was stoppered and vibrated for 3 minutes using an ultrasonic vibration machine at 3 (rc). Then, after standing at room temperature for 3 () minutes, the transition was carried out, and the residue was observed by visual inspection. When it was not confirmed that the residue was insoluble, it was judged that the solubility was good and it was recorded as 〇 in Table 2. Can be confirmed as insoluble matter

It is judged to be poor in the shape of It, and is referred to as X in Table 2. The results are shown in Table 2 〇' 0.5%: Compound 0·〇1 g 'Solvent 2 g 157651.doc s •30- 201209102 1 % : Compound 0.01 1 g, Solvent 1 g 3 % : Compound Ο. Ο 3 g, Solvent 1 g [Table 2]

Compound PGME EL ΝΜΡ 0.5% 5% 10% 0.5% 5% 10% 0.5% 1% 3% Example 1 (1-58) 〇〇〇〇〇〇〇〇〇 Example 2 (1-88) 〇〇〇 〇〇〇〇〇〇Comparative Example 1 (X) XXXXXXXXX Example 3 [Preparation of colored photosensitive resin composition] The following (A) to (E-1) were mixed to obtain a colored photosensitive resin composition. : (A) chromogen. Compound (1_5 8): Compound synthesized in Example 1 20 parts (B-1) Resin: methacrylic acid / benzyl methacrylate copolymer (Morby: 30/70; Weight average molecular weight 107 〇〇, acid value 7 〇 mg KOH/g) 50 parts (C-1) Polymerizable compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D-1) photopolymerization initiation Agent: Irgacure 〇χΕ〇1 (肟 compound; manufactured by BASF Japan Co., Ltd.) 15 parts (Ε-1) Solvent: propylene glycol monoterpene ether acetate 68 parts. Example 4 [Preparation of Colored Photosensitive Resin Composition] The following (Α)~(Ε-1) were mixed to obtain a colored photosensitive resin composition: (Α) Colorant. Compound (ug): Example Compound 2 synthesized in 2 157 157651.doc -31- 201209102 (Β-l) Resin: methacrylic acid / benzyl methacrylate copolymer (Morby: 3 0/70; weight average molecular weight 10700, acid value 70 mg KOH/g) 5 parts (C-1) polymerizable compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D-1) photopolymerization initiator: lrgacure οχΕΟΙ (肟 compound; BASF制造Manufactured by the company) 15 parts (E-1) solvent: 680 parts of propylene glycol monoterpene ether acetate. [Production of Color Filter] The colored photosensitive resin composition obtained above was applied onto a glass by a spin coating method to volatilize volatile components. After cooling, light irradiation was performed using a patterned quartz glass reticle and an exposure machine. After light irradiation, it was developed in an aqueous solution of potassium hydroxide, and heated to 2 〇〇〇c in an oven to obtain a color filter. From the results of Table 2, it was found that the compounds of the examples exhibited higher solubility for organic solvents. Industrial Applicability The compound of the present invention is useful as a dye. The compound of the present invention is excellent in solubility in an organic solution, and is particularly useful as a dye used for a color filter of a display device such as a liquid crystal display device. Further, the color-developing photosensitive resin composition containing the compound of the present invention can be produced in a known manner, including a color filter as a part of a constituent part thereof, and a known liquid crystal display (four), organic red device. Others, such as solid-state imaging devices, are related to colored images. 157651.doc

S • 32 ·

Claims (1)

201209102 VII. Patent application scope: 1. A compound represented by formula (1): [In the formula (), R represents a hydrogen atom or an aliphatic hydrocarbon having a carbon number of 丨 ......, which is contained in the aliphatic ketone group - which may be substituted; 'there is a hydrogen atom, a cyano group, or an amine sulfhydryl group; 1 indicates that the carbon number is a hospital base, the hydrogen atom contained in the alkyl group may be substituted by a halogen atom; A represents at least one group; one halogen atom and at least one _s 〇 3M benzoquinone represents hydrogen Atom or alkali metal atom]. ^The compound of item 1 wherein Α is a group represented by formula (1) ^s 〇 3m (1) 2) γ and γ independently represent a hydrogen atom or a halogen atom, and at least one of γ represents a halogen atom]. a compound of the epoch term 1 wherein R 丨 is -L 丨-X^R9, wherein "L1 represents a carbon number of alkanediyl; χι denotes &lt;〇·〇_; : a gas atom or a carbon number is The aliphatic nicotine group of the i-valent of (9), the _cii2- contained in the sulfhydryl group may be substituted by -0- or -CO-]. , I57651.doc 201209102 4. The compound of claim 3, wherein X1 is *-O-CO-, [where * represents a bond with L1]. 5. A dye which comprises the compound of claim 1 as an active ingredient. A colored photosensitive resin composition comprising: a coloring agent containing the dye of claim 5, a resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. 157651.doc a 201209102 IV. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbolic symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please reveal the characteristics that can best display the invention. Chemical formula: 157651.doc