TW201141958A - Compound - Google Patents

Abstract

A compound is represented by the formula (I): [In formula (I), R1 represents a hydrogen atom or a substitutable univalent C1-C30 alkyl group, wherein the –CH2– in said alkyl group can be substituted by –O– or–CO–; R2 represents a hydrogen atom, a cyano group or a carbamoyl group; R3 represents a C1-C4 alkyl group, wherein the hydrogen atom in said alkyl group can be substituted by halogen atom; R4~ R8 independently represents a hydrogen atom, a C1-C8 alkyl group, a C1-C8 alkoxyl group, a C2-C8 alkoxylalkyl group, a hydroxyl group, a cyano group, a nitro group, a halogen atom or a group represented by formula (Ia), and at least one group represented by formula (Ia).] [In formula (Ia), L1 represents a C1-C8 alkanediyl group]

Description

201141958 6. Description of the Invention: [Technical Field to Be Invented by the Invention] The present invention relates to a compound useful as a dye or the like. [Prior Art] The dye is used for color display using reflected light or transmitted light in, for example, a fiber material, a liquid crystal display device, or an ink jet printer. For example, in the first embodiment of the Japanese Patent Application Laid-Open No. 2GG4-263G, a compound represented by the following formula is disclosed.

The above compound is a dye excellent in light resistance and heat resistance, and is known as a water-based ink. On the other hand, the solubility of the compound in an organic solvent is low. It is easy to use β as a dye in a color filter for a display device such as a liquid crystal display device. [Invention] 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 carbon number which may have a substituent, and the {Hr contained in the hydrocarbon group may be substituted by _〇_ or _c〇_; 155940.doc 201141958 R2 represents a hydrogen atom, a cyano group or an amine fluorenyl group; R3 represents a radical of 1 to 4 carbon atoms. The hydrogen atom contained in the alkyl group may be substituted by a halogen atom; and R4 to R8 independently represent a hydrogen atom and a carbon number i~ An alkyl group of 8, an alkoxy group having 1 to 8 carbon atoms, an alkoxyalkyl group having 2 to 8 carbon atoms, a hydroxyl group, a cyano group, a nitro group, a halogen atom or a group represented by the formula (la), at least one Expressing the base represented by the formula (Ia)];

[In the formula (la), L1 represents an alkanediyl group having 1 to 8 carbon atoms]. [2] The compound according to [1], wherein R8 is a group represented by the formula (ia). [3] A compound of [1] or [2], wherein R1 is a group represented by ·l2_xir9: ', [where 'L2 represents a burnt number of 1 to 8; Χι means _c〇7; ^ It represents a nitrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, and _CH2- contained in the fatty smog group may be substituted by -〇- or -CO-]. [4] The compound according to any one of [1] to [3] wherein Ri is a group represented by fly 2, χΐ_ρ·X2-R1Q:

Base]. -0-C0-: [5] A compound such as [3] or [4], wherein X1 is [wherein * represents a bonding position with L2]. [6] The compound of any one of [1] to [5], wherein at least one of *r4 to rS is a nitro group. [7] A dye which is an effective component of the compound according to any one of (1) to [6]. [Effects of the Invention] The compound of the present invention is excellent in solubility in an organic solvent, and is excellent as a dye in a color filter used for a display device such as a liquid crystal display device. [Embodiment] The present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as a compound (1)). °

[In the formula (I), R represents a hydrogen atom or a carbon number 丨 to a monovalent hydrocarbon group which may have a substituent, and _CH2_ contained in the hydrocarbon group may be substituted by or _c〇_; R2 represents a hydrogen atom, a cyano group Or an amine group; R3 represents an alkyl group having 1 to 4 carbon atoms. The hydrogen atom contained in the alkyl group may be substituted by a dentate atom; and R4 to R8 each independently represent a hydrogen atom, an alkyl group having a carbon number of 8, An alkoxy group having 1 to 8 carbon atoms, an alkoxyalkyl group having 2 to 8 carbon atoms, a hydroxyl group, a cyano group, a nitro group, a halogen atom or a group represented by the formula (Ia), at least one represented by the formula (Ia) The basis of the representation. 155940.doc 201141958 [In the formula (la), L1 represents an alkanediyl group having 1 to 8 carbon atoms. As a monovalent hydrocarbon group which may have a substituent represented by R, a monovalent aliphatic hydrocarbon group, a monovalent aliphatic hydrocarbon group having a substituent, a monovalent alicyclic hydrocarbon group, and a one-valent alicyclic group having a substituent may be mentioned. A hydrocarbon group, a monovalent aromatic hydrocarbon group, a monovalent aromatic hydrocarbon group having a substituent, and a combination thereof, wherein the monovalent hydrocarbon group has a carbon number of 1 to 30. Examples of the substituent which the hydrocarbon group may have include a hydroxyl group, a carboxyl group, a thioalkyl group, an amine group which may be substituted with an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having a carbon number of 1-4. The aliphatic hydrocarbon group may, for example, be a methyl group, an ethyl group, a propyl group, an isobutyl butyl group, a second butyl group, a hexyl group, a heptyl group, an octyl group, a decyl group or a fluorenyl group. Examples of the aliphatic hydrocarbon group having a substituent include a 2-hydroxyethyl group, a 2-aminoethyl group, a 2-thioalkyl group, and the like. Examples of the alicyclic hydrocarbon group include a cyclopentyl group and a cyclohexyl group. Examples of the alicyclic hydrocarbon group having a substituent include 4-methylcyclohexyl ' 4 hydroxymethyl decyl group, 4-aminocyclohexyl group, 4-(N,N,-diamino)cyclohexyl group, and 2-amine. A cyclohexyl group, a 2-(N,N,-diamino)cyclohexyl group, a 4-carboxycyclohexyl group, a 4-methoxycyclohexyl group, a 2-carboxycyclohexyl group or the like. Examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group. Examples of the aromatic hydrocarbon group having a substituent include a 4-hydroxyphenyl group, a 4-methoxyphenyl group, a 2-carboxyphenyl group, and a 4-carboxyphenyl group. The above monovalent hydrocarbon group is preferably a carbon number “~", more preferably a carbon number of 2 to 16. The -CHr contained in the above hydrocarbon group may be substituted with _〇_4_c〇_ ^ in the above hydrocarbon group, preferably 2 ~4 -CHr is substituted into _〇_ or -C0_, more preferably 2 155940.doc 201141958 contiguous -CH; r is replaced by -CO- or -〇-. 2 is preferably -UX^R9 The group represented is more preferably a group represented by _l2_xI_l3·Π. If the RU is such a group, the solubility of the compound of the present invention in an organic solvent tends to increase. L2 and L3 are mutually independent carbon numbers. The alkanediyl group of 8 may, for example, be a benzyl group, an ethyl group, a propane-1,3-diyl group, a propane, a 2-diyl group, a butane 1,4-diyl group, a butyl group-1,3-di Base, butadiene%-diyl, pentane_1}5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octyl, etc. ^ Preferred carbon number The alkanediyl group of 1 to 5 is more preferably an alkanediyl group having 2 to 4 carbon atoms. It is preferably an alkanediyl group having 1 to 4 carbon atoms, more preferably an alkanediyl group having a carbon number of 22. X2 is -C0-0-. As Χι, preferably *_〇c〇 (* indicates the bonding position with 匕2). If X is *_〇_c〇_, it is easy to manufacture The compound of the invention: R9 is a hydrogen atom or a carbon number divalent aliphatic hydrocarbon group, and -CH2- contained in the aliphatic hydrocarbon group may be substituted by _〇_ or _c〇_. As an aliphatic hydrocarbon group representing R9, The aliphatic hydrocarbon group having 1 to 20 carbon atoms in the group exemplified as the monovalent aliphatic hydrocarbon group of the ruthenium, and more preferably the alkyl group of the carbon number (7). R10 is a hydrogen atom, a methyl group or an ethyl group. The group represented by the formula (Μ) to the formula (£_25) is exemplified as the -IAxLr9, and preferably -L2-X1_L3_X2_R10, for example, the formula (Μ)~ (f_2〇) The basis of the representation is more preferably a formula (f-Ι), a formula (f-2), a formula (f-5), an S(f_6), a formula (4), a formula (f_1〇), a <fl3 Further, the base represented by the formula (4), the formula (f-17), and the formula (f_18) is preferably a formula 屮2), a formula (f-6), a formula 屮10), a formula (M4), and a formula. (f l8) The base represented. 155940.doc 201141958

(M3) (M5)

(M4) (Μ6)

(M8) (f-2〇) 155940.doc 201141958

(f-22) ff*24) It is easy to purchase raw materials R2 is a hydrogen atom, a cyano group or an amine sulfhydryl group. Among them, in terms of aspect, a cyano group is preferred. Examples of the alkyl group having a carbon number of 丨4 in R3 include a methyl group, a methylide group, an isopropyl group, a n-butyl group, a second butyl group, a third butyl group, and the like; The dentate atom is substituted. Soil Bromine atom, etc. For example, examples of the functional atom include a fluorine atom, a chlorine atom, an alkyltrifluoromethyl group having a carbon number of 1 to 4 substituted with a halogen atom, and a pentafluoroethyl group. 'Carbon number 1 to 8 is 4, R3' is preferably a methyl group and a trifluoromethyl group, more preferably a methyl group, which is independently a hydrogen atom, an alkyl group having a carbon number of 1 to 8, and a carbon number. 2 to 8 of an alkoxyalkyl group, a base group, a gas group, a nitro group, a hydroxyl atom or a group represented by the formula (U), and at least one of the groups represented by the formula ((4). The compound (I) exists as The base represented by (la) is high. The lower tendency is because the solubility of the compound (I) in the organic solvent is improved by at least i of R4 to R8. The substance (1) is preferably used as r4~ R8, in addition to the formula ((4), the group has a hydrogen atom, a nitro group, an alkyl group having a carbon number, a chlorine group or a bromine group in addition to 155940.doc 201141958. Preferably, one of R is a formula (ia) In the above, R8 is preferably a group represented by the formula (la): &^ (la &gt; L1 is an alkanediyl group having 1 to 8 carbon atoms. As the alkanediyl group, The alkyl group having the carbon number of 1 to 8 is the same as the alkyl group. Preferably, as Li, the alkanediyl group having 1 to 4 carbon atoms is more preferably a fluorenylene group. Further, it is preferably R4 to R8. At least one of them is a nitro group. If the compound (1) has a nitrate In the case of R4 to Rs, the nitro group is preferably 1 or 2, more preferably 1. Among them, it is preferably "or the ruler 6 is a nitro group, and more preferably the R6 is a nitro group. If the nitro group is located at the same position, there is a tendency for the spectroscopic concentration to further increase the ratio. R R is preferably a group represented by the formula (Ia) and R 5 or R 6 is a nitro group, more preferably R 8 . The group represented by the formula (la), R5 is a hydrogen atom or a methyl group and R6 is a nitro group. R4 and R7 are preferably a hydrogen atom or an alkyl group having a carbon number of 6, and more preferably a hydrogen atom or a fluorenyl group. Examples of the alkyl group of the carbon number represented by R4 to R8 include a linear chain such as a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, and an n-octyl group. Alkyl; isopropyl, isobutyl, t-butyl, isopentyl, hydrazine-methylpentyl, decylpentyl, 3-mercaptopentyl, 4-mercaptopentyl, oxime-ethyl Butyl, 2_B 155940.doc .10- 201141958 butyl, 1-decylhexyl, 2-decylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 丨·B Pentyl, 2-ethylpentyl, 3-ethylpentyl, 1-propylbutyl, 1-(1- Benzyl)butyl, 1_(丨_methylethyl)_2_methylpropyl, 1-methylheptyl, 2-decylheptyl, 3-mercaptoheptyl, 4-methylheptyl, 5-decylheptyl, 6-fluorenylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-n-propylpentyl, 2-propyl Pentyl, 1-(1-methylethyl)pentyl, 丨-butylbutyl, tert-butyl, IP dimethylpropyl, 1,1-dimethylbutyl, 1,2-di Mercaptobutyl, iota, dimethylbutyl, 2,3-dimercaptobutyl, 1-ethyl-2-methylidenepropyl, 1, bismethylpentyl, 1,2- Dimercaptopentyl, iota, di-decylpentyl, iota, di-diylpentyl, 2,2-dimethylpentyl, 2,3-didecylpentyl, 2,4- Dimethylpentyl, 3,3-didecylpentyl, 3,4-dimethylpentyl, 1-ethyl-1-indenylbutyl, 1-ethyl-2-methylbutyl, 1-ethyl-3-methylbutyl, 2-ethyl-1-methylbutyl, 2-ethyl-3-methylbutyl, ι, ΐ-dimethylhexyl, ι, 2-di Methylhexyl, 1,3-dimethylhexyl, iota, di-diylhexyl, 1,5-dimethylhexyl, 2,2-didecylhexyl, 2,3-dimethylhexyl, 2 , 4- Dimethylhexyl, 2,5-didecylhexyl, 3,3-dimercaptohexyl, 3,4-dimercaptohexyl, 3,5-dimethylhexyl, 4,4-dimethylhexyl, 4,5-dimercaptohexyl, 1-ethyl-2-methylpentyl, 1-ethyl-3-methylpentyl, 1-ethyl-4-mercaptopentyl, 2-ethyl- 1-methylpentyl, 2-ethyl-2-mercaptopentyl, 2-ethyl-3-indolylpentyl, 2-ethyl-4-methylpentyl, 3-ethyl-1- Mercaptopentyl, 3-ethyl-2-methylindenyl, 3-ethyl-3-methylpentyl, 3-ethyl-4-mercaptopentyl, 1-propyl-1-methyl Butyl, 1-propyl-2-methylbutyl, 1-propyl-3-mercaptobutyl, 1-(1-decylethyl)-1-methylbutyl, 1-(1- Methyl ethyl) 155940.doc 201141958 -2-methylbutyl, i-(1)methylethyl)_3_methylbutyl, u-diethylbutyl, 1,2-diethylbutyl Chain alkyl. Examples of the alkoxy group having 1 to 8 carbon atoms 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. Oxyl and the like. Examples of the alkoxy group having 2 to 8 carbon atoms include a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, a methoxybutyl group, a methoxypentyl group, and an ethoxy group. Propyl, 2-ethoxypropyl, ethyloxy-hydrazine-methylethyl, -2-methyl-2-methoxyethyl, 1-(1-decylethoxy)propyl, 2_ (1_Methylethoxy)propyl, 1-(1-decylethoxymethylethyl, 2 (didecylethoxyethyl, 3-ethoxypropyl, etc. as a compound ( I), for example, a compound to a compound (1-126), etc. The column of 'R1 in Table 1 indicates the formula number of the above-exemplified group.

155940.doc -12· 201141958 [Table i] Compound R1 R2 R3 R4 R5 R6 R7 L 1 1-1 Μ CN ch3 HH no2. H ch2 1-2 f-3 CN ch3 HH no2 H ch2 1-3 f-4 CN ch3 HH NOz H ch2 1-4 f-5 CN ch3 HH no2 H ch2 1-5 f-6 CN ch3 HH N02 H ch2 1-6 f-7 CN ch3 . HH no2 H ch2 1-7 f-8 CN Ch3 HH . no2 H ch2 1-8 f-9 CN ch3 HH no2 H ch2 1-9 f-10 CN ch3 HH no2 H ch2 1-10 f-11 CN ch3 HH no2 H ch2 1-11 M2 CN ch3 HH no2 H ch2 1-12 f-13 CN ch3 HH no2 H ch2 1-13 f-15 CN ch3 HHN〇2 H ch2 1-14 f-16 CN ch3 HH no2 H ch2 1-15 M7 CN ch3 HH no2 H ch2 1 -16 f-18 CN ch3 HH no2 H ch2 卜1 7 f-19 CN ch3 HH no2 H ch2 1-1 8 f-20 CN ch3 HH no2 H ch2 1-19 f-22 CN ch3 HH N02 H ch2 1- 2 0 f-23 CN ch3 HH NO? H ch2 1-2 1 f-24 CN ch3 HH no2 H ch2 1-2 2 f-25 CN ch3 HHN〇2 H ch2 1-2 3 f-1 CN cf3 H ch3 HH ch2 1-2 4 f-3 H ch3 HH och3 H ch2 1-2 5 f-4 conh2 cf3 HHH CH2OCH3 ch2 1-2 6 f-5 CN ch3 HH OH H ch2 1-2 7 f-6 H cf3 H CN HH . ch2 1-2 8 f-7 conh2 ch3 FHHH ch2 1-2 9 f-8 CN cf3 H Cl HH ch2 1 -3 0 f-9 H ch3 HHB r H ch2 -13- 155940.doc 201141958 Bu 3 1 MO conh2 cf3 H ch3 HH ch2 1-3 2 f-11 CN ch3 HH och3 H ch2 1-3 3 M2 H cf3 HHH CH2OCH3 ch2 1-3 4 M3. conh2 ch3 HH OH H ch2 1-3 5 f-15 CN cf3 H CN HH ch2 1-3 6 f-16 H ch3 FHHH ch2 ϊ-3 7 f-17 conh2 cf3 H Cl HH Ch2 1-3 8 f-18 CN ch3 HHB r H ch2 1-3 9 f-19 H cf3 H ch3 HH ch2 1-4 0 f-20 conh2 ch3 HH och3 H ch2 1-4 1 f-22 CN cf3 HHH CH2OCH3 ch2 1-4 2 f-23 H ch3 HH OH H ch2 1-4 3 f-24 conh2 cf3 H CN HH ch2 1-4 4 f- 25 CN ch3 FHHH ch2 1-4 5 f-2 CN ch3 HH NOz H ch2 1-4 6 f-2 CN ch3 H NOj, HH ch2 1-4 7 f-2 CN ch3 N〇2 HHH ch2 1-4 8 f-2 CN ch3 HHH N02 ch2 1-4 9 f-2 CN Ch3 HH ch3 H ch2 1-5 0 f-2 CN ch3 HH och3 H ch2 1-5 1 f-2 CN ch3 HH ch2och3 H ch2 1-5 2 f-2 CN ch3 H . H OH H ch2 1-5 3 F-2 CN ch3 HH CN H ch2 1-5 4 f-2 CN ch3 HHFH ch2 1-5 5 f-2 CN ch3 HH Cl H ch2 1-5 6 f-2 CN ch3 HHB r H ch2 1-5 7 F-2 CN cf3 H ch3 HH ch2 1-5 8 f-2 H ch3 HH och3 H ch2 1-5 9 F2 conh2 cf3 HHH CH2OCH3 ch2 1-6 0 f-2 CN cf3 HH OH H ch2 1-6 1 f-2 H ch3 H CN HH ch2 1-6 2 . f-2 conh2 cf3 FHHH ch2 1-6 3 f-2 CN cf3 H Cl HH ch2 1-6 4 f-2 H ch3 HHB r H ch2 14- 155940.doc 201141958 卜 6 5 f-14 CN ch3 HH no2 H ch2 1-6 6 M4 CN ch3 H NOz HH ch2 1-6 7 F-14 CN ch3 no2 HHH ch2 1-6 8 M4 CN ch3 HHH no2 ch2 1-6 9 f-14 CN ch3 HH ch3 H ch2 1-7 0 f-14 CN ch3 HH och3 H ch2 1-7 1 f- 14 CN ch3 HH ch2och3 H ch2 1-7 2 f-14 CN ch3 HH OH H ch2 1-7 3 f-14 CN ch3 HH CN H ch2 1-7 4 f-14 CN ch3 HHFH ch-2 1-7 5 F-14 CN ch3 HH Cl . H ch2 1-7 6 f-14 CN ch3 HHB r H ch2 1-7 7 f-14 CN cf3 H ch3 HH ch2 1-7 8 f-14 H ch3 HH och3 H ch2 1 -7 9 f-14 conh2 cf3 HHH CH2OCH3 ch2 1-8 0 f-14 CN cf3 HH OH H ch2 ϊ-8 1 f-14 H ch3 H CN HH ch2 1-8 2 f-14 conh2 cf3 FHHH ch2 1- 8 3 f-14 CN cf3 H Cl HH ch2 1-8 4 f-14 H ch3 HHB r H ch2 1-8 5 f-21 CN ch3. HH no2 H ch2 1-8 6 f-21 CN ch3 H no2 HH Ch2 1-8 7 f-21 CN ch3 NO 2 HHH ch2 1-8 8 f-21 CN ch3 HHH no2 ch2 1-8 9 f-21 CN ch3 HH ch3 H ch2 1-9 0 f-21 CN ch3 HH och3 H ch2 1-9 1 f-21 CN ch3 HH ch2och3 H ch2 1-9 2 f-21 CN ch3 HH OH H ch2 1-9 3 f-21 CN ch3 HH CN H ch2 1-9 4 f-21 CN ch3 HHFH ch2 1-9 5 f-21 CN ch3 HH Cl H ch2 1-9 6 f-21 CN ch3 H . HB r H ch2 1-9 7 f-21 CN cf3 H ch3 HH ch2 1-9 8 f-21 H ch3 HH och3 H ch2 1-9 9 f-21 conh2 cf3 HHH CH2OCH3 ch2 Bu 1 0 0 f-21 CN Cf3 HH OH H ch2 . 1-1 0 1 f-21 H ch3 H CN HH ch2 1-10 2 f-21 conh2 cf3 FHHH ch2 1-10 3 f-21 CN cf3 H Cl HH ch2 •15- 155940.doc 201141958 .1-10 4 f-21 H ch3 HHB Γ H ch2 1-10 5 f-1 T3 _CN ch3 H no2 HH ch2 1-10 6 CN ch3 H no2 *HH ch2 Bu 1 0 7 f-4 CN ch3 H Γνο2 HH CHo 1-10 8 f-5 — — f-6 CN ch3 H no2 HH CH〇[-10 9 C NT ch3 H no2 &quot;h H CH〇1-110 f-7 CN ch3 [h N02 &quot; h HCH 2 Bu 1 1 1 r*8 CN — CHa HN〇2 HH ch2 Bu 1 1 2 CN ch3 H no2 HH CHo 1-113 f-10 CN ch3 H no2 HHCH 2 Bu 1 1 4 r*ll CN ch3 . H no2 Ji H CH〇1-115 f-12 CN ch3 H no2 HH CH〇卜1 1 6 r-13 — 丨— &gt;15 CN ch3 H no2 H ch9 Bu 1 1 7 CN ch3 H N02 HH ch2 Bu 1 1 8 f-16 . CN ch3 H no2 HH ch2 1-119 r*17 CN CHa HN〇2 &quot;h H. CHo 卜1 2 0 f 18 CN ch3 H no2 &quot;h H CH. Bu 1 2 1 f-19 ^20 CN ch3 H no2 HH ch2 1-12 2 CN ch3 H no2 &quot;h H CH〇卜1 2 3 r*22 T23 fu --' CN — ch3 H no2 1ϊ1 H ch2 1-12 4 _CN ch3 H no2 1 H CHo 1-12 5 CN ch3 H no2 HH CH〇1-12 6 I Λ0 CN ch3 HN〇 2 HH ch2 Among them, preferred are the compound (I-1) to the compound (1-22), the compound (I-45), the compound (1-46), the compound (1-65), the compound (][_66), and the compound. (1-85), compound (1_86) and compound (1_1〇5) to compound (1126), more preferably compound (1-45), compound (1-46), compound (1_65), compound (1-66) ), Compound (1_85), Compound (4)), Compound (M25), and Compound (1-86). When the compound (I) is such a compound, there is a tendency that the solubility of the organic solvent is high. For the selection of the compound of the invention _ 1 ... ~ called Gong Li. In the compound (1), for example, pure 8 is represented by the formula (IV), and the azo compound represented by the formula (IV) is clarified: the compound represented by the compound has a reaction group (combination), and 155940.doc - 16 - 201141958 (Iaa) A compound (hereinafter sometimes referred to as "compound (Iaa)"). In the case where any of R4 to R7 is a group represented by the formula (Ia), it may be produced in the same manner as the method for producing the compound (Iaa).

[In the formula (a4) and the formula (a5), Ri to R7 and the port represent the same meaning as described above^]

(Iaa) [In the formula (Iaa), ' Ri~R&gt; L1 means the same meaning as described above. The azo compound represented by the formula (4)) can be carried out according to the disclosure of Japanese Patent Publication No. 7. 88633, by the ratio of the diazonium salt represented by the formula (10) to the compound represented by the formula (IV). The diazonium salt represented by the diazo coupling can be obtained, for example, by diazotization of an amine represented by the formula (al) by using nitrous acid, nitrite or nitrite. _ /(a)f The H-butanone compound can be obtained, for example, by reacting a compound represented by the formula (a5) represented by the formula (4)) and a compound represented by the formula (10): 155940.doc • 17- 201141958

NHrR1 ΛΛ曰riA (a4) (a5) (a6) [In the formula (al), the formula (a2), the formula (a3), the formula (a4), the formula (a5), and the formula (a6), R1 to R7 represent The same meaning as above; ^ means an inorganic anion or an organic anion. The inorganic anion may, for example, be a fluoride ion, a vapor ion, a desert ion, a Wei-ion ion, a perchloric acid ion or a hypochlorous acid ion. Examples of the organic anion include CH3C〇〇·, phc〇〇· and the like. It is preferable to exemplify that the diazonium salt represented by the formula (a2) and the fluorenone compound represented by the formula (10) are linearly coupled in an aqueous solution by a vaporization ion, a desert ion, or a cH3C〇〇. An azo compound of the formula (d). The reaction temperature is preferably a shop, and more preferably =. The reaction time is preferably 1 hour to 2, more preferably H, and ~4 hours. As the above aqueous solvent, etc., water is preferred. The azo compound represented by the magic water, the methyl material 唆丨 4m (4) and the formula (4) are shown. The gamification reaction is carried out in the presence of an organic solvent to obtain the following: 155940.doc -18- 201141958 ((iv). In the acetalization reaction, a condensing agent is preferably used (Ioethyl_3·(3_2) Methylaminopropyl)carbodiimide hydrochloride and dicyclohexylcarbodiimide, etc.) and/or additives (Ν,Ν-dimethyl-4-amino group-specific spray pyridine, three Ethylamine, (±)-1〇-camphorsulfonic acid, etc.). The reaction temperature is preferably Μ, . . . , preferably for generations ~ bribe. The reaction time is preferably! hours ~ 12 hours, more preferably hours ~ 5 hours 0 The amount of the compound represented by the formula (10) is _ the azo compound i mole represented by the formula (10), preferably 〇.5 〜1 〇, more preferably 5 摩尔. Examples thereof include a ketone solvent such as toluene or xylene, a ketone solvent such as fluorene benzene, dichlorobenzene or chloroform in a hydrocarbon solvent, and a ketone solvent such as 'f-isobutyl ketone'.比 咯 轲 轲 & & & 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 Ii (ib) When the case where the manufacturing method shown sometimes referred to as "compound ⑽") into the play described.

(lb) [In the formula (lb), r2 to 尺 7 9 have the same meanings as described above by letting the formulas r Μ and LM. The diazonium (iv) of the ketone compound 1 is represented by the formula (10). It is produced by using the azo compound: a diazo coupling with the above formula (10) to produce I55940.doc •19- 201141958

In the formulae (b3) and (b4), R2 to R7 and L2 have the same meanings as described above. Then, an azo compound represented by the formula (b6) can be obtained by reacting an azo compound represented by the formula (b4) with a compound represented by the formula (b5) in the presence of an organic solvent. The reaction temperature is preferably 3 (rc~18〇&lt;&gt;c, more preferably 5〇 c ~ι2〇 c. The reaction time is preferably from 2 hours to 2 hours, more preferably from i hours to 4 hours.

In the formulae (b5) and (b6), R2 to r7 9 R and L are not the same as defined above, and Z represents a gas atom or a desert atom. ] Hydrocarbons such as f benzene and dif benzene are dissolved. Examples of the organic solvent include a sheet! Toluene gas such as benzene, benzene or chloroform, solvent, nitrobenzene solvent such as nitrobenzene, ketone solvent such as methyl isobutyl hydrazine, &quot;pyrrolidone special amine solvent. It is preferable that the compound of the formula (b5) is 1 mol with respect to the azo compound 1 mol represented by the formula (b4), and the compound is used in an amount of 1 mol or more and 8 mol or less and 4 mol or less. . Then, the compound Clb) can be obtained by subjecting the azo compound represented by the formula (b6) to the compound of the formula (4), I55940.doc 201141958, by the esterification reaction in the same manner as above. In the compound of the present invention, the compound (I) (* represents a bonding position with L2) of r^_l2_xi_r9 and χι is *_C〇_〇_, that is, the compound represented by the formula (Ic) (hereinafter sometimes referred to as The method for producing "compound (Ic)") will be described.

In the formula (Ic), R2 to R7, R9, and l1 and L2 have the same meanings as described above. By using the diazonium salt represented by the formula (a2) and the π-pyridone compound represented by the formula (c3), diazo coupling can be carried out by the same method as described above, whereby the diene represented by the formula (c4) can be produced. Nitrogen compounds.

In the formulae (c3) and (c4), R2 to R7 and L2 have the same meanings as described above. Then, an azo compound represented by the formula (c6) can be obtained by reacting an azo compound represented by the formula (c4) with a compound represented by the formula (c5) in the presence of an organic solvent. The reaction temperature is preferably 3 (rc~18 (rc, more preferably 50 C to 120 C. The reaction time is preferably from hours to 2 hours, more preferably from 1 hour to 4 hours. 155940.doc -21- 201141958) The organic solvent used herein may be the same as the solvent used in the reaction of the compound represented by the formula (d) and oxime: a solvent.

In the formula (10), R2 to R7, R9 and L2 represent the same as the above: azo compound 1 mol represented by Γ, and the formula (the compound used is 1 mol or more). Further, it is preferable that the reaction between the azo compound represented by the formula (c4) and the compound represented by the formula (IV) is preferably carried out for the purpose of smooth progress. As an acidic catalyst, Further, a mineral acid such as sulfuric acid or hydrochloric acid may be mentioned, but it is preferably ～4 mol, more preferably 0.8 to 2 mol, based on the compound 1 mol represented by the formula (G5). By using the azo compound represented by the formula (c6) and the compound represented by the formula (a3), the compound (4) obtained by the above-mentioned phase can be obtained from the reaction mixture. The method of obtaining the method is not particularly limited, and various methods well known in the art of the present invention can be used. For example, it is preferable that the red mixture is mixed with an acid (for example, acetic acid or the like) and water-mixed. Crystallization. The above acid is preferably prepared by previously preparing an aqueous solution of acid 155940.doc -22- 201141958. The reaction mixture is added to the above aqueous solution, and the temperature at which the reaction mixture is added is 1 Torr, 〇 or more and 5 〇〇 c or less, preferably 2 〇 ec or more and 50 ° C or less, preferably 20 ° C or more and 30 °. Further, it is preferred to add the reaction mixture to an aqueous acid solution and then stir at the same temperature for about 0.5 to 2 hours. The crystal obtained by filtration is preferably washed with water or the like, and then dried. Further, the dye may be further purified by a known method such as recrystallization. The dye of the present invention contains the compound (1) as an active ingredient. The dye of the present invention may be a dye containing only the compound (1). The dye of the present invention is preferably 70 to 100% by weight. The compound (I) is excellent in solubility in an organic solvent, and is useful as a coloring agent for coloring a photosensitive resin composition. As a coloring photosensitive resin composition containing the compound (I), A coloring agent containing a compound of the present invention (hereinafter sometimes referred to as "coloring agent (A)"), a resin (B), and a photopolymerizable compound (〇, light) are listed. A colored photosensitive resin composition of the polymerization initiator (d) and the solvent (E). The coloring agent (A) may further contain a dye and/or a pigment different from the compound (1) in addition to the compound (1). For dyes other than (I), the chromaticity index (c〇1〇ur)

Index) (published by The Society of Dyers and Colourists) classified as Solvent, Acid, Basic, Reactive, Direct, DiSperse, or vat Compounds, etc. More specifically, the dye of the chromaticity index (CI) number as described below is exemplified, but is not limited thereto. 155940.doc -23· 201141958 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; CI solvent orange 41, 54, 56, 99; CI acid orange 56, 74, 95, 108, 149, 162; CI · reaction orange 16; CI · Direct orange 26; CI solvent red 24, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 160, 218; CI acid red 73, w, 92, 97, 138, 151 211, 274, 289; CI acid violet i〇2; CI solvent green i, 5; CI acid green 3, 5, 9, 25, 28; c · I · green 1; CI · reduction green 1 and so on. As the pigment, an organic material or an inorganic pigment which is usually used in a pigment dispersion resist can be mentioned. A, 丨 is a machine pigment, and may be exemplified by a metal compound such as a metal oxide or a metal salt, and specifically, iron, cobalt, aluminum, braid, ship, copper, uranium, metal-avoiding Oxide. Oxides or composites of metals such as locks, chrome, rhetoric, and recording are also used as organic pigments and inorganic pigments, specifically by color 155940.doc -24 - 201141958 (Colour Index) (The Society of Dyers and Colourists ) Compounds classified as Pigment. More specifically, a pigment having a chromaticity index (C.I.) number as described below is exemplified, but is not limited thereto. CI Pigment Yellow 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173 and 180; CI Pigment Oranges 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 and 71; CI Pigment Red 9, 97, 105, 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. 10, 15, 25, 36 and 47, etc. The content of the colorant (A) is preferably 5 to 60 parts by mass based on 100 parts by mass of the solid content component in the colored photosensitive resin composition. Here, the solid material is formed into a knife, which means a total of components other than the solvent in the coloring photosensitive resin composition. The content of the compound (1) in the colorant (A) is preferably from 3 to 1% by mass. The compound (I) and the dye and pigment different from the compound (1) may be used singly or in combination of two or more kinds. The resin (B)' is not particularly limited, and any resin may be used. The resin (B) is preferably a soluble resin, more preferably a resin having a structural unit derived from (meth)acrylic acid. Here, (mercapto)acrylic acid means acrylic acid 155940.doc -25- 201141958 and/or methacrylic acid. Specific examples of the resin (B)' include a mercaptoacrylic acid/methacrylic acid benzylic acid copolymer, a methacrylic acid/methyl acrylic acid benzyl vinegar/styrene copolymer, and a methacrylic acid/mercapto group. Benzyl acrylate / isobutyl methacrylate copolymer, methacrylic acid / styrene / benzyl methacrylate / N_phenyl maleimide copolymer, methacrylic / styrene / sulfhydryl Glycidyl acrylate copolymer and the like. The polystyrene-equivalent weight average molecular weight of the tree (B) is preferably 5,000 to 35,000', more preferably 6,000 to 30,0 Å. The acid value of the resin (B) is preferably from 5 Torr to 150, more preferably from 6 Torr to 135. The content of the resin (B) is usually 7 to 65 parts by mass, preferably 13 to 6 parts by mass, per 100 parts by mass of the solid content of the colored photosensitive resin composition. When the polymerizable compound (C) is a compound capable of starting polymerization by an active radical, an acid or the like generated from a polymerization initiator (D) by the action of light or heat, it is not particularly limited as a polymerizable compound (C). Examples of the compound having a polymerizable carbon-carbon unsaturated bond and the like can be mentioned. The polymerizable compound (C) is preferably a photopolymerizable compound having three or more polymerizable groups. Here, the polymerizable group means a group in which a polymerization reaction is carried out by the above-mentioned living radical, acid or the like. Examples of the photopolymerizable compound having 93 or more polymerizable groups include pentaerythritol tetraacrylic acid brewing, pentaerythritol tetramethyl (tetra) (tetra), dipentaerythritol pentaacetic acid vinegar, dipentaerythritol pentamethylpropene (tetra), and dipentaerythritol. Hexaacryl 155940.doc • 26. 201141958 酉a, pentaerythritol hexamethacrylate, etc. The above polymerizable compound (c) may be used singly or in combination of two or more kinds. The molecular weight of the polymerizable compound (C) is usually from 150 to 800 Å, preferably from 19 Å to 7 Å. The content of the polymerizable compound (C) is preferably 5 to 65 parts by mass, more preferably 10 to 60 parts by mass, per 100 parts by mass of the solid content of the colored photosensitive resin composition. Examples of the polymerization initiator (D)' include a living radical generator, an acid generator, and the like. The living radical generating agent produces free radicals due to the action of light or heat. Examples of the living radical generating agent include 2—fluorenyl-2-indolyl-1-(4-methylsulfanylphenyl)propanone and 2—transalkyl-2-methylbenzene. Propi-1-one, benzoin dimethyl ketal, 2-hydroxy-2-methyl-(2-hydroxyethoxy)phenyl]propane ketone, oxime-hydroxycyclohexyl Phenyl ketone and other phenethyl _ compounds; 2-isopropyl-9-oxathiazinium, 4-isopropyl-9-oxathione, 2,4-diethyl-9-oxothione, 9-oxosulfonium compound such as 2,4-dichloro-9-oxosulfonium, anthracene-gas-carboxypropanyl group _9_ oxythiopurine p-star; 2,4-bis(trichloroindenyl)- 6-(4-methoxyphenyl)-indole, three tillage, 2,4-bis(dichloromethyl)-6-(4-methoxynaphthyl)_1,3,5-three tillage, 2,4-bis(trimethylmethyl)-6-(4-methoxystyryl tri-p well, 2,4-bis(tris-methyl)-6·[2-(5-methylfuran) -2-yl)vinyl]-n% three tillage, 2,4_bis(trimethylsulfonyl)-6-[2-(furan-2-yl)vinyl]_ι, 3,5-three tillage, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-indolylphenyl)vinyl bromide, ^three tillage, 2,4-bis(trichloromethane) Base)_6_[2-(3,4-dimethoxyphenyl)B基卜丨,^ 155940.doc -27- 201141958 Three tillage and other three tillage compounds; 2,4,6·trimethylbenzhydryldifluorene, a base phosphine oxide, 2,2,-bis(o-chlorobenzene ))-4,4',5,5'-tetraphenyl _12,- 啐 啐 0 Λ 1 Λ oxazolyl, 10-butyl-2-acacridone, 2_ethyl hydrazine, benzoin , 9,1 〇-韭μ, phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene compound, etc. As the above acid generator, for example, triphenyl silk material _(4)' 4_Ethyloxyphenyl dimethyl s-p-toluene sulphate, diphenyl hydrazine p-toluene sulfonic acid ― ^ ηηχ· ^ — sulfonium salt such as hexafluoroantimonate or nitrate The benzyl sulfonium sulfonate is a sulfonate sulfonate, a benzoin toluene salt, etc. The above photopolymerization initiator (1) 丨 can be tilted / * m. UJT is used alone or two kinds of The content of the photopolymerization initiator (9) is preferably 〇1 to 3〇% by mass, more preferably u mass 4, based on the total amount of the resin (B) and the photopolymerizable compound (C). When the polymerization initiator is combined with μ, +. f 3 is in the above range, high sensitivity It is preferred to use a solvent (E) as a solvent (E), for example, an ether, a ketone, an alcohol, an ester, an indigoamine, etc. as the above-mentioned shouting 'for example, a stone丨丨 and ._ + + j enumeration. Tetrahydrofuran, tetrahydropyran, M-II, No. 11 hospital, ethylene glycol monomethyl ether, c-private single-b-ethylene glycol monopropyl, ethylene glycol monobutyl With, diethylene glycol armor secret, -7 two-ply soap, acetaminophen monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol - A-7-side ^ 呷 monomethyl ether, one ethylene Alcohol diethyl ether, di-6 glycol decyl ether, diethylene glycol dipropyl ether, decylene glycol dibutyl ether, propylene glycol monomethyl ether, propylene glycol monoacetin, propylene glycol monopropyl ether, diglycol monomethyl thioacetate Ester, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene 155940.doc -28- 201141958 alcohol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether Acid ester, diethylene glycol monobutyl ether acetate, and the like. Examples of the above ketones include acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, 4-hydroxy-4-mercapto-2- Pentanone, cyclopentanone, cyclohexanone, and the like. Examples of the alcohol include hexanol, cyclohexanol, ethylene glycol, and glycerin. Examples of the ester include ethyl acetate, n-butyl acetate, isobutyl sulfonium acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, and ethyl butyrate. Ester, butyl butyrate, decyl lactate, acetaminophen, butyl lactate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, decyl ethoxylate, ethoxylate Ethyl acetate, decyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 2-methoxypropionic acid Anthracene ester, 2, methoxypropionic acid, hydrazine, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-decyloxy- Methyl 2-mercaptopropionate, ethyl 2-acetoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, decyl acetate, ethyl acetate , 3-methoxybutyl acetate, 3-mercapto-3-indolyl butyl acetate, γ-butane vinegar, and the like. Examples of the above guanamine include hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethylacetamide, and hydrazine-methyl group. More than the remaining ones. These solvents may be used singly or in combination of two or more. The content of the solvent (E) in the colored photosensitive resin composition is preferably from 70 to 95% by mass, more preferably from 75 to 9 % by mass, based on the color of the photosensitive photosensitive resin composition. I55940.doc -29- 201141958 The colored photosensitive resin composition of the present month may also contain an interface active agent, a filler, other polymer compound, adhesion promoter, anti-oxidation d, antimony absorbing agent, light, if necessary. Various additives such as stabilizers and chain transfer agents. The compounds of the invention are useful as dyes. It is useful especially as a dye in a color filter for a display device such as a liquid crystal display device because of its solubility to an organic solvent. Further, the above colored photosensitive resin composition can be used in a well-known manner for a display device including a color light-receiving sheet as a part of its constituent parts (for example, a well-known liquid crystal display device, organic EL (mectr〇l Uminescent, electroluminescence) A device associated with various colored images, such as a solid-state imaging device, etc. [Embodiment] Next, the present invention will be described more specifically by way of examples and the like. In the examples, reference examples, and comparative examples, The % of use and the part are referred to as the mass basis unless otherwise specified. In the following examples, the structure of the compound is by NMR (Nuclear)

Magnetic Resonance (NMR) (JMM-ECA-500, manufactured by Nippon Electronics Co., Ltd.) was confirmed. Example 1 After adding 80 parts of water to 5 parts of 5-nitro-o-amine benzoic acid (Tokyo Chemical Industry Co., Ltd. &amp; 2 parts), 4 parts of sodium hydroxide hydrazine was added to dissolve it, and it was cooled under ice bath. 19.7 parts of a 35% aqueous solution of sodium nitrite was added, followed by addition of 35 °/. 26 parts of hydrochloric acid, and dissolved for 2 hours to obtain a suspension containing diazonium salt. 155940.doc -30- 201141958 On the other hand, 26.0 parts of ethyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 2 parts of cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), and 2% aminoethanol (Wako Pure Chemical Industries Co., Ltd.) Manufactured) 24.4 parts of the mixture, and dropped for 24 hours at 95 ° C. After cooling the reaction solution to room temperature, it was added to a mixture of 3 parts of water and 35 parts of 35% hydrochloric acid, and stirred at room temperature. The precipitated crystals were taken as a residue for suction filtration, and then dried to obtain 20.4 parts of the compound represented by the formula (d).

Then, 20.4 parts of the compound represented by the formula (d1) was suspended in 1 part of water, and the pH was adjusted to 9.0 using sodium hydroxide. To the above, the suspension containing the diazo rust salt was dropped over 15 minutes using a pump. After dropping the knot, it was further stirred for 30 minutes, thereby obtaining a yellow suspension. Stir for an hour. The yellow solid obtained by filtration was dried under reduced pressure at 60 ° C to obtain 38.7 parts of the compound of formula (d2).

25.7 parts of the compound represented by the formula (d3) was added to 3 parts of the compound represented by the formula (d2), and the mixture was stirred for "hours" in the solvent of the N-methylpyrrolidone. 37.0 parts in water, confirming the structure by iH_NMR to obtain the compound represented by formula (d4) 155940.doc •31·201141958

&lt;Identification of the compound represented by the formula (d4)&gt; ^NMR^^ooh, 0, 2.49 (2H, t), 2&gt;49 (2^^ 2^^ 4 3.9M2H, q), U0 (2H, t), 4.23 (2H, 8 i6 (ih ' 8.46 (1H, dd), 8.70 (1H, d), 14.5 〇 (1H bs) i5 56 (iH small) '30.2 parts of the compound represented by the formula (4)) Add (±) ι〇 to the acid (10) parts, Ν, Ν·dimethyl ketone group. 3.25 parts, 2,3 epoxy oxime 15·2 parts and gas copying Into this suspension, a solution obtained by dissolving 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in 197 parts of chloroform was maintained at 5°. The temperature of the crucible is dropped on one side. After the completion of the dropwise addition, the mixture is stirred at room temperature for 5 hours. After the reaction, the mixture is washed with 1 N hydrochloric acid and saturated brine. The organic layer is taken out using a separating funnel, and dried by adding sulfuric acid. The solvent was distilled off by a rotary evaporator to remove the solvent, and then dried under reduced pressure at 6 (rc) to give the compound (yield of formula (1-45).

&lt;Identification of the compound represented by the formula (1-45)&gt; 155940.doc -32-201141958^-NMR: 1.10 (3H, t), 2.49 (2H, t), 2.49 (2H, t), 2.56 ( 3H, s), 2.83 (2H, m), 3.45 (1H, m), 3.97 (2H, q), 4.11 (2H, t), 4.23 (2H} t), 4.45 (2H, m), 8.21 (1H , d), 8.51 (1H, dd)5 8.74 (1H, d), 15.03 (1H). 0.10 g of the compound represented by the formula (1-45) obtained was dissolved in dimethylformamide to have a volume of 250 cm3, and 2 cm3 of the obtained compound was diluted with ethyl lactate to have a volume of 100 cm3 (concentration: 0.0080 g/L), an absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-650DS: manufactured by Sakamoto Seiki Co., Ltd.) (quartz cell, optical path length: 1 cm). The compound is in the form of nm, which is a vivid yellow color, and the molar absorption coefficient indicates a high value of 48,000. Comparative Example 1 In Example 1, 2-aminoterephthalic acid was used instead of 5-nitro-o-amine benzoic acid, and a compound represented by the formula (el) was used instead of the compound represented by the formula (d1). The compound represented by the formula (1) was obtained in the same manner as in Example 1.

The obtained compound 〇.35 g represented by the formula (1) is dissolved in dimethyl ketone

_ ----/ a) (Quartz tank, optical path length amine to make the volume of 250 1 release and volume of 100 cm photometer (V-650DS: 155940.doc -33· 201141958 length: 1 cm) The absorption spectrum was Xmax = 440 nm, and the molar absorption coefficient was 42,000. [Evaluation of Solubility] The compound obtained in Example 1 and Comparative Example 1 was calculated as follows for the propylene glycol monoacetic acid test. Vinegar (hereinafter referred to as PPGEA (PropyIene Glycol Monomethyl Ether Acetate)), propylene glycol mono-square scale (hereinafter referred to as PGME (Propylene Glycol Monomethyl Ether)), lactic acid ethyl acetate (hereinafter referred to as EL (Ethyl Lactate)), N-methyl ° The solubility of each bit ketone (hereinafter referred to as NMP (N-methylpyrrolidone)). In a 50 mL sample tube, the compound and the above solvent are mixed in the following ratio, and then the sample tube is sealed, and the ultrasonic wave is used at 30 ° C The shaker was shaken for 3 minutes, and then left to stand at room temperature for 30 minutes, and then filtered to visually observe the residue. When the insoluble matter as a residue could not be confirmed, it was judged that the solubility was good, and it was recorded as 〇 in Table 2. Can confirm that it is not In the case of the substance, it was judged to be poor in solubility, and it was represented by X in Table 2. The results are shown in Table 2. 0.5% Compound 0·01 g, solvent 2 g 1% Compound 0.01 g, solvent 1 g 3% Compound 0.03 g Solvent 1 g [Table 2]

Compound PGMEA PGME EL NMP 0.50% 1% 3% 0.50% 0.50% 0.50% 1% 3% Example 1 1-45 〇〇〇〇〇〇〇0 Comparative Example 1 i XXXXXXXX I55940.doc -34- 201141958 Reference Example 1 [Preparation of Colored Photosensitive Resin Composition] The following compounds were mixed to obtain a colored photosensitive resin composition: (1-45) Colorant: Compound synthesized in Example 1 20 parts (B-1) Resin: mercaptoacrylic acid /benzyl methacrylate copolymer (mole ratio: 30/70; weight average molecular weight 10700, acid value 70 mgKOH/g) 70 parts (C-1) polymerizable compound: dipentaerythritol hexaacrylate (sputum chemical) Manufactured by the company) 30 parts (D-1) photopolymerization initiator. Benzene dimethyl ketal ([rgacure 651: manufactured by Ciba Japan Co., Ltd.) 15 parts (E-1) Solvent: N, N-dimethyl 680 parts of methotrexate. [Production of color filter] The colored photosensitive resin composition obtained above was applied by spin coating to volatilize volatile components. After cooling, light irradiation was performed using a patterned quartz glass reticle and an exposure machine. After the light irradiation, development was carried out by using an aqueous solution of hydrogen hydroxide to remove the color filter by oven heating. Example 2 After adding 80 parts of water to 18 parts of 4-potassium o-benzolic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 'sodium hydroxide 〇 4 parts was added and dissolved. After cooling in an ice bath, 19 8 parts of a 35% aqueous solution of sodium nitrite was added, and then 26.1 parts of 35% hydrochloric acid was added little by little to dissolve and stirred for 2 hours to obtain a suspension containing a diazo rust salt. Then, the compound represented by the formula (dl) was suspended in 3 parts of 155940.doc • 35- 201141958 In 100 parts of water, the pH was adjusted to 9.0 using sodium argon. The above suspension containing the diazonium salt was dropped into the bath by using a pump for 15 minutes. After the completion of the code, the mixture was further stirred for 30 minutes, whereby a yellow suspension β 'α was obtained for 1 hour. The yellow solid obtained by filtration was dried under reduced pressure at 6 ° C to give 38.4 parts of the compound of formula (d5).

(d5) 鉴定 &lt;Identification of the compound represented by the formula (d5)&gt; 'H-NMR: 2.38 (3H, s), 3.53 (2H, dd), 3.89 (2H, t), 5.23 (1H, bs) , 7.83 (1H, dd), 8·04 (1H, d), 8·11 (1H, d), 16.56 (1H, s). To 30 parts of the compound represented by the formula (d5), 25.6 parts of the compound represented by the formula (d3) was added and stirred at 7 ° C for 3 hours in a solvent of N-decylpyrrolidone. After the completion of the reaction, the mixture was placed in water to obtain 36.9 parts of the compound represented by the formula (d6). Use 丨11 to confirm the structure with 1\411.

&lt;Identification of the compound represented by the formula (d6)&gt; 'H-NMR: l.ii (3H, t), 2.48 (2H, t), 2.48 (2H, t), 2.55 (3H, s), 3.95 (2H, q), 4.09 (2H, t), 4.22 (2H, t), 7.83 (1H, dd), 155940.doc •36· 201141958 8.〇4 (1H,d),8.11 (1H,d) , 14.52 (1H, bs), 15.54 (1H, s). In the 30.1 parts of the compound represented by the formula (d6), 1.89 parts of (±)_i〇_樟 brain acid, 3 2 parts of N,N-dimethyl 4-aminopyridine, 2,3 epoxy are added. 15.3 parts of propanol and 450 parts of chloroform at 5. (: stirring was carried out. To the suspension, 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was dissolved in 197 parts of the gas-form. The solution was kept at a temperature of 5 ° 3 (the temperature was dropped). After the completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. After the completion of the reaction, the mixture was washed with 1 N hydrochloric acid and a saturated aqueous solution of sodium chloride. The filtrate was dried and filtered, and the filtrate was evaporated to dryness on a rotary evaporator, and then dried under reduced pressure at 6 〇〇 CT to obtain a compound of the formula (1-46). The structure was confirmed by lpi NMR.

<Identification of the compound represented by the formula (1-46)> ^-NMR: MO (3H, t), 2.49 (2H, t), 2.49 (2H, t), 2.56 (3H, s), 2.83 (2H , m), 3.45 (1H} m), 3.97 (2H, q), 4.11 (2H, t), 4.23 (2H, t), 4.45 (2H, m), 7.83 (1H, dd), 8.04 (1H, d), 8.11 (1H, d), 15.10 (1H). The obtained compound represented by the formula (1-46) is dissolved in dimethylformamide t to a volume of 250 cm 3 , and 2 cm 3 thereof is diluted with lactic acid ethyl acetate 155940.doc • 37- 201141958 The volume was 100 cm3 (concentration: 0.0080 g/L), and the absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-650DS: manufactured by JASCO Corporation) (quartz cell, optical path length: 1 cm). The compound is Xmax=425 nm, which is bright yellow, and the molar absorption coefficient indicates a high value of 48000. Example 3 25.4 parts of the compound represented by the formula (d7) is added to 30.2 parts of the compound represented by the formula (d5). The mixture was stirred at 7 ° C for 3 hours in a solvent of N-decylpyrrolidone. After the completion of the reaction, the mixture was placed in water to obtain 37·3 parts of the compound represented by the formula (d8). The structure was confirmed by W-NMR.

—N=

:02H &lt;Identification of the compound represented by the formula (d8)&gt; H-NMR: 0·75 (3H), 0.77 (3H), 1.08 (2H), 1.18 (2H), 1.37 (2H), 1.42 (2H ), 2.16 (1H), 2.55 (3H), 4.11 (2H), 4.23 (2H), 7_83 (1H), 8.04 (1H), 8.11 (1H), 14.50 (1H), 15.03 (1H). To the 3 parts of the compound represented by the formula (d8), 1.89 parts of (±) 1 camphorsulfonic acid, 3 26 parts of N,N-didecyl-4-aminopyridine, 2,3_epoxypropyl 15.4 parts of alcohol and 450 parts of gas were stirred underneath. To the suspension, 17 parts of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was dissolved. The solution obtained in 197 parts of the sample was dropped while maintaining the temperature of 5 t. After the completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. After the reaction is completed, it is washed with ^N hydrochloric acid and saturated salt. Use the liquid separation material to remove 155940.doc •38_ 201141958 machine layer 'Add magnesium sulfate to dry' to filter. The solvent was distilled off by a rotary evaporator, and dried under reduced pressure at 6 (TC) to yield 28.4 parts of the compound of formula (1-86). The structure was confirmed by ijj-NMR.

&lt;Identification of the compound represented by the formula (1-86)&gt; H_NMR: 0.75 (3H), 0.77 (3H), 1.08 (2H), 1.18 (2H)' 1.37 (2H), 1.42 (2H), 2.16 (1H), 2.55 (3H), 2.83 (2H), 3.45 (1H), 4.11 (2H), 4.23 (2H), 4.45 (2H), 7.83 (1H), 8.04 (1H), 8 11 (1H), 15.03 (1H). The obtained compound represented by the formula (1-86) is dissolved in dimethylformamide to a volume of 250 cm 3 ', 2 cm 3 of which is diluted with ethyl acetate to make a volume of 100 cm 3 (Concentration: 0.008 g/L), and an absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-650DS: manufactured by Sakamoto Seiki Co., Ltd.) (quartz cell, optical path length: 1 cm). The compound is Xmax = 425 nm, which is a bright yellow color, and the Mohr absorbance coefficient indicates a high value of 48,000. Example 4 To a solution of 30.0 parts of the compound represented by the formula (d2), 25.2 parts of the compound represented by the formula (dy) was added, and the mixture was dropped in 7 ° C for 3 hours in a solvent of N-methylpyrrolidone. After completion of the reaction, the mixture was poured into water to obtain 36.9 parts of a compound represented by the formula (d9). The structure was confirmed by 1H-NMR. 155940.doc -39- 201141958

&lt;Identification of the compound represented by the formula (d9)&gt; W-NMR: 0.75 (3H), 0.77 (3H), (2H), i i8 (2H), i 37 (2H), 1.42 (2H), 2.16 (1H), 2.55 (3H), 4.11 (2H)5 4.23 (2H) 8.22 (1H), 8.50 (1H), 8.75 (1H), 14.50 dHMs.osdH). 5 Compound 30 represented by formula (d9) In addition, add (±) i〇樟 brain acid 1.89 parts, N,N-dimercapto-4-amino acridine 3 27 parts, 2,3 • epoxy small propanol and gas imitation 450 Share, at 5. (: stirring is carried out. To the suspension, a solution obtained by dissolving a salt of ethyl ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in 197 parts of the gas is prepared. While maintaining the temperature, the surface was dripped. After the completion of the dropwise addition, the mixture was allowed to stand at room temperature for (4) for 5 hours. After the reaction was completed, the mixture was washed with 1 N hydrochloric acid and saturated brine. After the filtrate was distilled off by a rotary evaporator, the solvent was evaporated under reduced pressure to give 28.4 parts of the compound of formula (1-85).

&lt;Identification of the compound represented by the formula (1-85)&gt; 155940.doc •40- 201141958 iH-NMR: 0.75 (10), 0·77 (3H), 1.08 (2H), 1.18 (2H), 1.37 (2Η) ), 1.42 (2Η), 2·16 (1Η), 2.55 (3Η), 2.83 (2Η), 3.45 (1Η), 4.11 (2Η), 4.23 (2Η), 4.45 (2Η), 8.20 (1Η), 8.53 (1H), 8.76 (1H), 15.05 (1H). The obtained compound (0.10 g) represented by the formula (1-85) was dissolved in dimethylformamide to have a volume of 250 cm 3 ', 2 cm 3 of which was diluted with ethyl lactate to have a volume of 100 cm 3 (concentration: 0.008 g/L), the absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-650DS: manufactured by Sakamoto Separation Co., Ltd.) (quartz cell, optical path length: 1 cm). The compound is Xmax = 435 nm, which is a bright yellow color, and the molar absorption coefficient indicates a high value of 48,000. Example 5 After adding 80 parts of water to 18.1 parts of 5-nitro-o-amine benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 4 parts of sodium hydroxide was added to dissolve it. After cooling in an ice bath, add 19.7 parts of a 35% aqueous solution of sodium nitrite, and then add a point of 35 °/. 26.2 parts of hydrochloric acid was dissolved and stirred for 2 hours to obtain a suspension containing a diazo-stack salt. On the other hand, 26.0 parts of ethyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 2 parts of cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), and 8 parts of decylaminoethanol (manufactured by Wako Pure Chemical Industries, Ltd.) 30.0 parts were mixed and stirred at 95 t for 24 hours. After the reaction solution was cooled to room temperature, it was added to a mixture of water and 35 parts of 35% hydrochloric acid, and (iv) was cooled at room temperature for an hour. The precipitated crystal was taken out as a residue for suction filtration, and then dried to obtain 21.9 parts of the compound represented by the formula (d 10). 155940.doc •41- 201141958

(dio) &lt;Identification of the compound represented by the formula (dio)&gt; H-NMR: 1·1〇(3H,t), 2.49 (2H,t), 2.49 (2H,t).,2.56 (3H , s), 3.96 (2H, q), 4.10 (2H, t), 4.23 (2H, t), 8.16 (1H, d), 8.46 (1H, dd), 8.70 (1H, d), 14.50 (1H, Bs), 15.56 (1H, s). Then, 21.9 parts of the compound represented by the formula (dlO) was suspended in 100 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. To this, the above suspension containing the diazonium salt was dropped by a pump for 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. The yellow solid obtained by filtration was reduced to 60 under reduced pressure. (: Drying was carried out to obtain 42.3 parts of the compound represented by the formula (dll).

Η (&lt;«1) &lt;Identification of the compound represented by formula (dll)&gt; ^H-NMR: 1.12 (3H), 2.38 (3H), 3.53 (2H), 3.89 (1H), 5.23 (1H) , 8.21 (1H), 8.52 (1H), 8.75 (1H), 15.44 (iH). '32.9 parts of the compound represented by the formula (dll) is such that 25.7 parts of the compound represented by the formula μ" is added to the N-methyl group. Each of the ketones, Xuanqi, &lt; After stirring for 3 hours, the reaction mixture was poured into water to obtain 38.0 parts of the character represented by the formula (dl2). The structure was confirmed by H-NMR. No &amp; 155940.doc • 42· 201141958

&lt;Formula (identification of the compound represented by (112)&gt; • H-NMR: 1.10 (3H), 1.12 (3H), 2.49 (2H), 2.49 (2H), 2.56 (3H), 3.96 (2H), 4.10 (2H), 4.23 (1H), 8.16 (1H), 8.46 (1H), 8.70 (1H), 14.50 (1H), 15.56 (1H). In the 31.0 parts of the compound represented by formula (dl2),士)-10-1.8% of camphoric acid, 3.25 parts of N,N-dimercapto-4-aminopyridine, 15.2 parts of 2,3-epoxy-1·propanol and 450 parts of gas, at 5° Stirring was carried out under C. To the suspension, a solution obtained by dissolving 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in 197 parts of a gas sample was dissolved. The mixture was dropped while maintaining the temperature of 5 ° C. After the completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. After the completion of the reaction, the mixture was washed with 1 N hydrochloric acid and a saturated aqueous solution of sodium chloride. The mixture was dried and filtered, and the solvent was evaporated to dryness on a rotary evaporator, and dried under reduced pressure to afford 29.7 parts of the compound of formula (1-65). The structure was confirmed by W-NMR.

&lt;Identification of the compound represented by the formula (1-65)&gt; 155940.doc •43·201141958 'H-NMR: 1.10 (3H), 1.12 (3H), 2.49 (2H), 2.49 (2H), 2.56 ( 3H), 2.83 (2H), 3.45 (1H), 3.97 (2H), 4.11 (2H), 4.23 (1H), 4.45 (2H), 8.21 (1H), 8.51 (1H), 8.74 (1H), 15.50 ( 1H) » Dissolve 0.10 g of the compound represented by the formula (1-65) in dimercaptoamine to make a volume of 250 cm3, and dilute 2 cm3 of it with ethyl lactate to make a volume of 100 cm3 (Concentration: 0.008 g/L), and an absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-650DS: manufactured by Sakamoto Seiki Co., Ltd.) (quartz cell, optical path length: 1 cm). The compound is in the form of nm and has a bright yellow color, and the molar absorption coefficient indicates a high value of 48,000. Example 6 After adding 80 parts of water to 183 parts of 4-nitro-o-amine benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 4 parts of sodium hydroxide was added and dissolved. After cooling in an ice bath, 19.7 parts of a 35% aqueous sodium nitrite solution was added, and then 26.2 parts of 35% hydrochloric acid was added little by little to dissolve and stirred for 2 hours to obtain a suspension containing a diazo rust salt. Then, 9 parts of the compound represented by the formula (d10) was suspended in 1 part of water, and the pH was adjusted to 9. To this, the above suspension containing the diazonium salt was dropped by a pump for 15 minutes. After the end of the drip, the sandalwood was mixed for 30 minutes, and the yellow county obscenity car heart/child was obtained. After stirring for 1 hour, the yellow solid obtained by filtration was dried under reduced pressure at 6 ° ° C, and 42.5 parts of the compound of formula (dl3) was obtained.

155940.doc •44- 201141958 &lt;Identification of the compound represented by formula (dl3)&gt; H-NMR. 1.12 (3H), 2.38 (3H), 3.53 (2H), 3·89 (1H) 5 23 (1H ), 7:83 (1H), 8.04 (1H), 8.11 (1H), 15.95 (ιΗ). 25.7 parts of the compound represented by the formula (d3) was added to 32.9 parts of the compound represented by the formula (d 13), and stirred in a solvent of N-mercaptopyrrolidone at 7 Torr (&gt;c for 3 hours). After completion of the reaction, the mixture was poured into water to obtain 36.9 parts of the compound represented by the formula (dl4). The structure was confirmed by 4^11.

&lt;Determining the compound represented by the formula (dl4)&gt; ^-NMR: 1.1〇(3H), 1.12 (3H), 2.49 (2H), 2.49 (2H), 2.56 (3H), 3.96 (2H), 4.10 (2H), 4.23 (1H), 7.83 (1H), 8.04 (1H), 8.11 (1H), 14.50 (1H), 15.56 (1H). In the 30 parts of the compound represented by the formula (dl4), 1.89 parts of (±)_1 camphorsulfonic acid, 3.25 parts of N,N-dimethyl-4-aminopyridine, and 2,3-epoxypropyl group were added. 15.2 parts of alcohol and 450 parts of chloroform were stirred at 5 °C. To the suspension, a solution obtained by dissolving 16.4 parts of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in 197 parts of chloroform was maintained at 5. The temperature of the sputum drops on one side. After the completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. After the completion of the reaction, the mixture was washed with 1 N hydrochloric acid and saturated brine. The organic layer was taken out using a separatory funnel, dried over magnesium sulfate and filtered. The filtrate was distilled off by a rotary evaporator to remove the solvent, and then dried under reduced pressure at &lt;RTI ID=0.0&gt;&gt;&gt; Confirmation of structure by h-NMR

&lt;Identification of the compound represented by the formula (1-66)&gt; ^-NMR: 1.10 (3H)S 1.12 (3H), 2.49 (2H), 2.49 (2H), 2.56 (3H), 2.83 (2H), 3.45 (1H), 3.97 (2H), 4.11 (2H)5 4.23 (1H), 4.45 (2H), 7.83 (1H), 8.04 (1H), 8.11 (1H), 15.80 (1H). The compound o.io g represented by the formula (1-66) was dissolved in dimethylformamide to a volume of 250 cm3, and 2 cm3 of the solution was diluted with ethyl lactate to a volume of 100 cm3. (Concentration: 0.008 g/L), an absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V-650DS: manufactured by JASCO Corporation) (quartz cell, optical path length: 1 cm). This compound is λιη£ιχ = 424 nm, and has a bright yellow 'Mole absorbance coefficient indicating a high value of 48,000. Example 7 To a solution of 30.5 parts of the compound represented by the formula (dl3), 27.0 parts of the compound represented by the formula (d7) was added in a solvent of N-methylpyrrolidone at 7 〇β (: 3 hours). After completion, it was placed in water to obtain 37.2 parts of the compound represented by the formula (dl5). The structure was confirmed by W-NMR. o2n h3c cn : o2h ho (dl5) 155940.doc • 46 · 201141958 &lt; represented by formula (015) Identification of the compound &gt; ^-NMR: 0.75 (3H), 0.77 (3H), 1.08 (2H), 1.14 (3H), 1.18 (2H), 1.37 (2H), 1.42 (2H), 2.16 (1H), 2.55 (3H), 4.11 (2H), 4.23 (1H), 7.83 (1H), 8.04 (1H), 8.11 (1H), 14.48 (1H), 15.01 (1H). Compound 3 represented by formula 15) 8.8 parts, adding 1.± parts of (±)-1〇_camphorsulfonic acid, 3.26 parts of N,N-dimethyl-4-aminopyridine, 15.4 parts of 2,3-epoxy-1-propanol and 450 parts of chloroform, at 5. (: stirring is carried out. To the suspension, a solution obtained by dissolving 17 parts of 1-ethyl-3-(3-diaminopropyl) carbodiimide hydrochloride in 197 parts of chloroform While dropping at a temperature of 5 ° C, it was stirred at room temperature for 5 hours. After the completion of the reaction, it was washed with 1 N hydrochloric acid and saturated brine. The organic layer was taken out using a separating funnel. The mixture was dried and filtered, and the solvent was evaporated to dryness using a rotary evaporator, and then dried under reduced pressure at 6 ° C to obtain 28.3 parts of the compound of formula (M25). The structure was confirmed by h-NMR.

&lt;Calculation of the compound represented by the formula (1-125)&gt; H-NMR: 0.75 (3H), 0.77 (3H), 1.08 (2H), 1.15 (3H), M8 (2H), 1.37 (2H) , 1.42 (2H), 2.16 (1H), 2.55 (3H), 2.83 (2H), 3·45 (1H), 4.11 (2H), 4.23 (1H), 4.45 (2H), 7.83 (1H), 8. 〇4 155940.doc -47· 201141958 (1H), 8.11 (1H), 15.03 (1H) » The obtained compound I_l〇g represented by the formula (I-125) is dissolved in dimethyl decylamine. The volume was 250 cm3, and 2 cm3 of it was diluted with lactic acid to make a volume of 1 〇〇cm3 (concentration: 〇〇〇8 g/L), using an ultraviolet-visible spectrophotometer (V-650DS: 曰本Spectroscopic (manufactured) (quartz cell, optical path length: 1 cm) The absorption spectrum was measured. The compound was Xmax = 425 nm, and the yellow 'mole absorptivity coefficient of the fresh disk indicates a high value of 48 Å. Example 8 To a 30 part of the compound represented by the formula (dll), 26.8 parts of the compound represented by the formula (d7) was added, and the mixture was stirred at 7 °t for 3 hours in a solvent of N-methylpyrrolidone. After completion of the reaction, the mixture was poured into water to obtain 37.1 parts of the compound represented by the formula (dl6). The structure was confirmed by h-NMR.

&lt;Identification of the compound represented by the formula (dl6)&gt; h-NMR: 0.75 (3H), 0.77 (3H), us (2Η), ι ΐ4 (3H), 丄18 (2H), 1.37 (2H), 1.42 4.23 (1H), 8_21 (1H), 8.51 (1H) s

Urt), 8.74 (1H), 14.48 (1H) 15.01 (1H). ' Compound represented by formula (dl6) 3〇.6 parts towel*丄,, 1 cut dry 'added (±)-10- camphorsulfonic acid 1.89 parts, N,N-dimercapto-4-aminopyrrolidine, &lt;3.26 parts, 15.4 parts of 2,3-epoxy-1-propanol and 450 parts of gas-like, and the mixture was mixed at 5 °C. To the suspension 155940.doc •48· 201141958, a solution obtained by dissolving 1-ethyl small (3-dimethylaminopropyl)carbodiimide hydrochloride i7 in 197 parts of chloroform. The surface is kept while the temperature of yc is kept dropping. After the completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. After completion of the reaction, it was washed with 1 N hydrochloric acid and saturated brine. The organic layer was taken out using a separatory funnel, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness using a rotary evaporator, and then dried under reduced pressure at 6 ° C to obtain 28.6 parts of the compound of formula (1-21). The structure was confirmed by iH_NMR.

&lt;Identification of the compound represented by the formula (1-21)> H-NMR: 0.75 (3H), 0.77 (3H), 1.08 (2H), 1.15 (3H), 1.18 (2H), 1.37 (2H) , 1.42 (2H), 2.16 (1H), 2.55 (3H), 2.83 (2H), 3.45 (1H), 4.11 (2H), 4.23 (1H), 4.45 (2H), 8.23 (1H), 8.55 (1H) , 8.78 (1H), 15.24 (1H). The compound 〇·1 〇g represented by the formula (1-21) was dissolved in diterpene amide to make a volume of 250 cm 3 '2 cm 3 of which was diluted with ethyl lactate to make a volume of 1 〇〇cm3 (concentration: 0.008 g/L), the absorption spectrum was measured using a UV-visible spectrophotometer (V-650DS: manufactured by Sakamoto Separation Co., Ltd.) (quartz cell, optical path length · 1 cm). This compound is human max = 433 nm, and the yellow 'mole absorptivity coefficient of the fresh disk indicates a high value of 48,000. With respect to the compounds obtained in Examples 2 to 8, the solubility was evaluated by the same method as in Example 1 by the method of I55940.doc • 49·201141958. The results are shown in Table 3 [Table 3]

From the results of Tables 2 and 3, it is understood that the compounds of the examples exhibit high solubility in organic solvents. Reference Example 2 A coloring photosensitive resin composition and a color filter were obtained in the same manner as in Reference Example 1 except that the compound synthesized in Example 11 was replaced with the compound synthesized in Example 2. Reference Example 3 A coloring photosensitive resin composition and a color filter were obtained in the same manner as in Reference Example 14 except that the compound synthesized in Example 1 was replaced with the compound synthesized in Example 3. Reference Example 4 A coloring photosensitive tree I55940.doc -50·201141958 fat composition and color filter were obtained in the same manner as in Reference Example 1, except that the compound synthesized in Example 10 was replaced with the compound synthesized in Example 4. sheet. Reference Example 5 A coloring photosensitive resin composition and a color filter were obtained in the same manner as in Reference Example 1 except that the compound synthesized in Example 1 was replaced with the compound synthesized in Example 5. Reference Example 6 A coloring photosensitive resin composition and a color filter were obtained in the same manner as in Reference Example 1 except that the compound synthesized in Example 1 was replaced with the compound synthesized in Example 6. Reference Example 7 A colored photosensitive resin composition and a color filter were obtained in the same manner as in Reference Example except that the compound synthesized in Example 1 was replaced with the compound synthesized in Example 7. Reference Example 8 A colored photosensitive resin composition and a color filter were obtained in the same manner as in Reference Example except that the compound synthesized in Example 1 was replaced with the compound synthesized in Example 8. The colored photosensitive resin composition containing a compound of sei can produce a color filter which produces less impurities and is high in quality. [Industrial Applicability] The compound of the present invention is excellent in solubility in an organic solvent, and is excellent as a dye in a color filter used for a display device such as a liquid crystal display device. 155940.doc -51-

Claims (1)

201141958 VII. Patent application scope: 1. A compound' is represented by formula (1): (I) [In the formula (1), R1 represents a hydrogen atom or a carbon number which may have a substituent, and a -2 hydrocarbon group contained in the hydrocarbon group, and -CH2- contained in the hydrocarbon group may be substituted by _〇_ or ·(:〇_ R represents a hydrogen atom, a cyano group or an amine carbenyl group; R represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted by a halogen atom; RR independently represents a hydrogen atom and a carbon number 丨An alkyl group of ～8, an alkoxy group having 1 to 8 carbon atoms, an alkoxyalkyl group having 2 to 8 carbon atoms, a hydroxyl group, a cyano group, a nitro group, a dentate atom or a group represented by the formula (la), at least One expression (the base represented by one sentence); [In the formula (la), L1 represents an alkanediyl group having 1 to 8 carbon atoms]. 2. The compound of claim 1, wherein R8 is a group represented by formula (ia). 3. The compound of claim 1, wherein Ri is a group represented by _L2_xl_R9, wherein [L2 represents an alkanediyl group having a carbon number of 1 to 8; X1 represents ·〇〇_〇_; and r9 represents a hydrogen atom Or a one-carbon aliphatic hydrocarbon group having 1 to 20 carbon atoms, and -CH2- contained in the aliphatic nicotinic group may be substituted by -〇- or -CO-]. 155940.doc 201141958 4. If you are looking for items! a compound wherein r1 is a group represented by _l2_x1_L3: in the form of -R [wherein, L2 and X1 represent the same meanings as above; L3 represents a carbon number dibasic; &amp; means that hunger r1° represents a hydrogen atom, a methyl group Or 5. 6. 7. For example. The compound of claim 3 or 4, wherein χ丨 is *_〇_c〇_: [where, * represents the bonding position with L2]. The compound of item 1, wherein at least one of (10) is dyed as an active ingredient as claimed in the claims. 155940.doc 201141958 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 best indication of the characteristics of the invention. Chemical formula: 155940.doc