TW201217337A - characterized by having higher molar absorption coefficient, thereby being suitable to be useful as a dye contained in colored photosensitive resin composition - Google Patents

Abstract

The present invention provides a compound represented by formula (I), which is useful as a dye contained in a colored photosensitive resin composition by having a higher molar absorption coefficient. In formula (I), R1 represents a hydrogen atom or a monovalent C1 to C20 aliphatic group, wherein the –CH2– contained in the aliphatic group can be replaced by –O– or –CO–; R2 represents a hydrogen atom, a cyano group or a carbamoyl group; R3 represents a C1 to C4 alkyl group, wherein the hydrogen atom contained in the alkyl group can be replaced by halogen atom; R4 to R8 respectively represent a hydrogen atom, a C1 to C8 alkyl group, a C1 to C8 alkoxy group, a C2 to C8 alkoxyalkyl group, a hydroxyl group, a cyano group, a nitro group or a –SO3M, wherein at least one in R4 to R8 represents a nitro group, and at least one represents a –SO3M therein; and M represents a hydrogen atom or an alkali metal atom.

Description

201217337 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a compound and a colored photosensitive resin containing the same. [Prior Art] Dyes, for example, in the fields of fiber materials, liquid crystal display devices, ink jets, and the like, can be used for color display using reflected light or transmitted light. As such a dye, for example, a compound represented by the following formula in JP-A-2-153977 is known.

The above compounds may not be sufficient from the viewpoint of the molar absorption coefficient. SUMMARY OF THE INVENTION The present invention provides the following [1] to [6]. Π] A compound of the formula (I).

In the formula (1), R1 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, and the _CH2- contained in the aliphatic hydrocarbon group may be substituted by -〇- or -CO-. 158021.doc 201217337 R2 represents a hydrogen atom, a cyano group or an amine carbenyl group. R3 represents a carbon group having 1 to 4 carbon atoms. The hydrogen atom contained in the alkyl group may be substituted by a halogen atom. R4 to R8 independently of each other represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having a carbon number, an alkoxyalkyl group having 2 to 8 carbon atoms, a hydroxyl group, a cyano group, a nitro group or -SOsM 'R4 At least one of -R8 represents a nitro group, and at least one represents -SO3M 0 Μ represents a hydrogen atom or a metal atom. [2] The compound of the above [1], which is represented by the formula (Η).

[In the formula (II), R1, R2, R3 and ]ν [respectively mean the same meaning as described above]. [3] The compound according to [1] or [2] above, wherein Ri is ny. [L1 represents a carbon number of 8 alkanediyl β χΐ represents _c〇_〇_. R9 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 17 carbon atoms, and -CH2_ contained in the aliphatic hydrocarbon group may be substituted by -?- or -CO-. Here, the carbon numbers of L1, χΐ and R9 are 20 or less in total. [4] The compound according to the above [3], wherein χΐ is "〇_c〇[* represents a bond to L1]. [5]-type dye is as in any of the above (1) to [4] The compound of the present invention is an active ingredient. [6] A coloring photosensitive resin composition comprising a compound, a resin and a solvent as in [丨] to 158021.doc 201217337. A compound (hereinafter sometimes referred to as a compound ( 〖)). The present invention is represented by formula (I)

In [弋(), R represents an atom or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, and -ch2- contained in the fat 2 group smoke* may be substituted by -〇_ or _c〇·. R2 represents no hydrogen atom, cyano group or amine sulfhydryl group. R3 represents a carbon group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a halogen atom. R4 to R8 independently of each other represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, 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 or _ At least one of S〇3M 'R4 to R8 represents a nitro group, and at least one represents -SO3M. Μ represents a hydrogen atom or an alkali metal atom]. The i-valent aliphatic hydrocarbon group represented by R1 may, for example, be an alkyl group such as a mercapto group, an ethyl group, a propyl group, an isobutyl group, a butyl group, a tert-butyl group, a group, a decyl group or a fluorenyl group. The hexyl group, the heptyl group, and the octyl group contained in the above aliphatic hydrocarbon group may be substituted by or ·c〇_. Examples of such a group include _C2H4-〇_c6h12, _C2H4_〇_c2h4-o-c2h5'-C2H4-CO-C6H12, -C2H4-C2H4-0-C2H4-C0-C6H12. C2H4-〇_c〇-〇-c6Hi2 and R1 are preferably -LLxLr9. When R1 is -Αχ1#, there is a tendency that the solubility of the compound 158021.doc 201217337 of the present invention is improved in an organic solvent, which is preferable. R9 is a hydrogen atom or a carbon number aliphatic ketone group, and -CH2- contained in the aliphatic ketone group may be substituted by 〇_ or -C0_. The aliphatic hydrocarbon group which is r9 is exemplified by the number of carbon atoms 1 to 17 in the core group as the i-valent aliphatic hydrocarbon group represented by the ruler. The monovalent aliphatic smog group represented by R- or -CO-substituted R9 may be -L2_x2-R10. R is a hydrogen atom, a methyl group or an ethyl group. L1 and L2 are each independently a carbon number of alkanediyl', and examples thereof include a methylene group, an ethyl group, a propane-1,3.diyl group, a propane-1,2-diyl group, and a butane], 4_ Di-butyrate ι, 3-_-yl, pentyl m-diyl, hexyl, hexyl-diyl, & -1,7-diyl and octyl-1,8-diyl. X and X are -co-o-. In particular, χι is preferably *_〇 c〇 (* indicates a key bond with ^). When X1 is *_0_C0_, it is easy to produce the compound 0 of the present invention as -LLxLr9, and examples thereof include a group represented by any one of the formulae (Μ) to (f_25). In each formula, • indicates a bond with a nitrogen atom. In the above, as -LLxLd-Rio, for example, a group of the formula (fl) to the formula (f2〇) can be cited. Preferably, it is a formula (Μ), a formula (f_2), a formula (f_5), a formula, a formula (f-9), a formula (f-10), a formula (f_13), a formula (f l4), a formula (f) L7), a group represented by any one of the formula (1). 18), the formula (f-21), and the formula (f_24), more preferably a formula (f-2), a formula (f-6), or a formula (f) a group represented by any one of the formula (6) 4), the formula ^_18), the formula ^_21), and the formula (f-24), and more preferably a formula (f_2), a formula (f-14), or a formula The base shown by any of (f-21) and (f_24). 158021.doc • 6 - 201217337

•CH3 (f-1) CH3 (f-3)

(f-2) (M)

(f-5) CH3 (f-7)

(f-6) (f-8) <?η3φ^°·

O

.CH3 (f-9)

(f-11) ?H3^K^0· PH3

O

Or xh,

.〇, /CH3 (f-12) o (M3)

0.

'CH3 (f-14) (f-15)

(f-16) ^ch3 ,ch3

.CH3 (M7)

, CH3 (f-19) ^ch3 <ch3 0

Ό XH, (f-18)

.CH, _ .ch3 •Ό,^ /CH3

•CH,

Ch3 (f-22> 158021.doc 201217337

Examples of the alkyl group having a carbon number of 4 represented by R3 include a methyl group, a propyl group, an isopropyl group, an n-butyl group, a second butyl group, and a third butyl group. The hydrogen atom contained in it may also be substituted by a fang atom. The base and the normal alkyl group are as a south atom, and examples thereof include a fluorine atom, a gas atom, and (d). Examples of the substituent of the carbon number of the hydrogen atom substituted by the imine atom include a trifluoromethyl group and a pentafluoroethyl group. 4 is preferably R3' and is preferably a fluorenyl group and a trifluoromethyl group, more preferably a methyl group. R to R independently of each other represent a gas atom +, a carbon number of 8 burnt groups, a carbon number of 1 to 8 alkoxy group, a carbon number of 2 to 8 of a silk group, (4), a cyano group, an exact group or a ruthenium 3M. The one of the RRs is Shi Xiaoji, and at least one of them is _s〇3M. Niobium is a hydrogen atom or an alkali metal atom. Examples of the alkali metal include lithium, sodium, and potassium. Μ' is preferably a hydrogen atom and a sodium atom is more preferably a hydrogen atom. The alkyl group having a carbon number of 1 to 8 is, for example, methyl, ethyl, n-propyl-n-butyl-n-decyl, n-hexyl, or a linear alkyl group such as heptyl or n-octyl; and isopropyl, isobutyl, t-butyl, isopentyl, i-methylpentyl, 2-decylpentyl, 3-methylpentyl, 4-methylpentyl, ethyl ethyl butyl, ethyl butyl, hexyl S, 2-decyl hexyl, 3-methylhexyl, 4-methyl 158021.doc 201217337 hexyl, 5-methylhexyl, 1- Ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 1-propylbutyl, 1-(1-decylethyl)butyl, 1-(1-methylethyl)- 2-methylpropyl, 1-decylheptyl, 2-methylheptyl, 3-decylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-n-propylpentyl, 2-propylpentyl, 1-(1-indolylethyl)pentyl , 1-butylbutyl, 1-butyl-2-decylbutyl, 1-butyl-3-methylbutyl, 1-(l,1-dimethylethyl)butylbutyl, Third butyl, 1,1-dimethylpropyl, 1,1_ Mercaptobutyl, 1,2-dimethylbutyl, 1,3-di-f-butyl, 2,3-dimethylbutyl, 1-ethyl-2·mercaptopropyl, 1,1 - a fluorenyl group, 1,2-dimercaptoalkyl, 1,3 -didecylpentyl, 1,4-dimethylpentyl, 2,2-dimethylpentyl, 2, 3-dimercaptopentyl, 2,4-dimercaptopentyl, 3,3-dimercaptopentyl, 3,4-diindenyl, 1-ethyl-1-methylbutyl, 1-ethyl-2-mercaptobutyl, 1-ethyl-3-methylbutyl, 2-ethyl-1-indenylbutyl, 2-ethyl-3-methylbutyl, 1, 1_dimercaptohexyl, 1,2-didecylhexyl, 1,3-didecylhexyl, iota,di-diylhexyl, 1,5-didecylhexyl, 2,2-didecyl Hexyl, 2,3-didecylhexyl, 2,4-didecylhexyl, 2,5-dimethylhexyl, 3,3-didecylhexyl, 3,4-methylhexyl, 3,5 - monomethylhexyl, 4,4-dimethylhexyl, 4,5-dimercaptohexyl, 1-ethyl-2-mercaptopentyl, 1-ethyl-3-indolylpentyl, 1_ Ethyl-4-methylpentyl, 2-ethyl-1-indenylpentyl, 2-ethyl-2-mercaptopentyl, 2-ethyl-3-indenylpentyl, 2-ethyl -4-methylpentyl, 3-ethyl_1_methylpenta , 3-ethyl-2-mercaptopentyl, 3-ethyl-3-methylpentyl, 3-ethyl-4-methylpentyl, 1-propyl-1-decylbutyl, Io_propyl_2_mercaptobutyl, 1-propyl-3-mercaptobutyl, 1-(1-methylethyl)_ι_methylbutyl, ι_ 158021.doc 201217337 〇Methyl B A branched alkyl group such as 2-methylbutyl, -methylethyl) 3_f-butyl, M-diethylbutyl or 1,2-diethylbutyl. 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. Hexyloxy. Examples of the oxyalkyl group having a carbon number of 2 to 8 include an anthracenyloxy group, a methoxyethyl group, a methoxypropyl group, a methoxybutyl group, a methoxypentyl group, and an ethoxy group. Propyl, 2-ethoxypropyl, ethyloxy decylethyl, buckwheat ethoxyethyl, 1_(1·methylethoxy)propyl, 2_(丨-methyl Oxy)propyl, 1-(1-mercaptoethoxy)-methylcarbonyl, and 2-(1-methylethoxy)-1-methylethyl, 3-ethoxypropyl. As the compound (I), a compound represented by the formula (11) is preferred.

In the formula [11], R, R, r3 & m respectively represent the same meaning as described above]. When the right cleavage substance (I) is a compound represented by the formula, there is a tendency that the molar absorption coefficient is further increased. One ? The compound (1) is more preferably a compound represented by the formula (Η), from the viewpoint of the workability of the oxime.

(冚) 158021.doc 201217337 [In the formula (III), R1, R2, R3 and M respectively have the same meanings as described above]. In the formula (III), R1' is preferably a group represented by the above _li_xi_r9, and among them, a formula (f-Ι), a formula (f-2), and a formula (f-5) 'f (f-6) are preferable. ), formula (f-9), formula (fl〇), formula (f-13), formula (f-14), formula (f_n), formula (f-18), formula (f-21) and formula ( More preferably, the formula (f_2), the formula (f_6), the formula (fl〇), the formula (f-14), the formula (f_18), and the formula (f_21) Further, the base ' represented by any one of the formulas (f_24) is preferably a group represented by any one of the formula (f2), the formula (fl4), the formula (f-21), and the formula (f-24). R2' is preferably a cyano group, and as R3, a methyl group and a trifluoromethyl group are more preferably a methyl group. The compound (I) ' may, for example, be a compound to a compound (1 - 102). The r1 to rS systems described in Table 1 correspond to the formula (1-〇). Further, the block of Ri records the number of the formula of the above-exemplified base. For example, the compound (?_i) is a compound represented by the following formula (1-1).

158021.doc -11 - 201217337 Table 1

Compound R1 R2 R3 R4 R5 R6 R7 R8 1-1 f-1 CN ch3 so3H HN〇2 HH 1-2 f-3 CN ch3 N〇2 H S03H HH 1-3 f-4 CN ch3 HN〇2 S03H HH 1 -4 f-5 CN ch3 so3H HN〇2 HH 1-5 f-6 CN ch3 N〇2 H S03H HH 1-6 f-7 CN ch3 HN〇2 S03H HH 1-7 f-8 CN ch3 so3H HN〇 2 HH 1-8 f-9 CN ch3 N〇2 H S03H HH 1-9 f-10 CN ch3 HN〇2 S03H HH 1-10 f-11 CN ch3 so3H HN〇2 HH 1-11 f-12 CN ch3 N〇2 H S03H HH 1-12 f-13 CN ch3 HN〇2 S03H HH 1-13 f-15 CN ch3 so3H HN〇2 HH 1-14 f-16 CN ch3 N〇2 H S03H HH 1-15 f -17 CN ch3 HN〇2 S03H HH 1-16 f-18 CN ch3 so3H HN〇2 HH 1-17 f-19 CN ch3 N〇2 H S03H HH 1-18 f-20 CN ch3 HN〇2 S03H HH 1 -19 f-22 CN ch3 so3H HN〇2 HH 1-20 f-23 CN ch3 N〇2 H S03H HH 1-21 f-25 CN ch3 HN〇2 S03H HH 1-22 f-1 CN cf3 S03H OH N 〇2 HH 1-23 f-3 H ch3 N〇2 H so3h ch3 H 1-24 f-4 conh2 cf3 HN〇2 so3H H CN 1-25 f-5 CN ch3 S03H CH2OCH3 N〇2 HH 1-26 f -6 H cf3 N〇2 H so3h OCH3 H 1-27 f-7 CONH2 ch3 HN〇2 so3H H OH 1-28 f-8 CN cf3 S03H ch3 N〇2 HH 1-29 f-9 H ch3 N〇2 H so3h H CN 1-30 f-10 CONH2 cf3 S03H CH2OCH3 N〇2 HH 1-31 f-11 CN ch3 N〇2 H so3h OCH3 H 1- 32 f-12 H cf3 HN〇2 so3H H OH

1-33 f-13 CONH2 ch3 so3h ch3 N〇2 H H 1-34 f-15 CN cf3 N〇2 H S03H CN H 158021.doc -12- 201217337

1-35 f-16 H ch3 HN〇2 S03H H CH2OCH3 1-36 f-17 conh2 cf3 so3H och3 N02 HH 1-37 f-18 CN ch3 N〇2 H S03H H OH 1-38 f-19 H cf3 so3h Ch3 N〇2 HH 1-39 f-20 conh2 ch3 N〇2 H S03H CN H 1-40 f-22 CN cf3 H N02 S03H H CH2OCH3 1-41 f-23 H ch3 so3H OCH3 N〇2 HH 1-42 F-25 CN ch3 N〇2 H S03H OH H 1-43 f-2 CN ch3 so3h H N02 HH 1-44 f-2 CN ch3 N〇2 H S03H HH 1-45 f-2 CN ch3 H N02 S03H HH 1-46 f-2 CN ch3 so3H OH N〇2 HH 1-47 f-2 CN cf3 N〇2 H S03H ch3 H 1-48 f-2 conh2 ch3 HN〇2 S03H H CN 1-49 f-2 H Cf3 so3H CH2OCH3 N02 HH 1-50 f-2 conh2 ch3 N〇2 H S03H OCH3 H 1-51 f-2 CN ch3 HN〇2 S03H H OH 1-52 f-2 CN cf3 so3H ch3 N〇a HH 1- 53 f-2 CONH2 cf3 N〇2 H S03H H CN 1-54 f-14 CN ch3 so3h HN〇2 HH 1-55 f-14 CN ch3 N〇2 H S03H HH 1-56 f-14 CN ch3 HN〇 2 S03H HH 1-57 f-14 CN ch3 so3H OH N〇2 HH 1-58 f-14 CN cf3 N〇2 H S03H ch3 H 1-59 f-14 conh2 ch3 HN〇2 S03H H CN 1-60 f -14 H cf3 so3H CH2OCH3 N〇2 HH 1-61 f-14 CONH2 ch3 N〇2 H so3h OCH3 H 1-62 f- 14 CN ch3 H N〇2 so3H H OH 1-63 f-14 CN cf3 S03H ch3 N〇2 H H 1-64 f-14 CONH2 cf3 N〇2 H so3h H CN

1-65 f-21 CN ch3 so3h HN〇2 HH 1-66 f-21 CN ch3 N〇2 H S03H HH 1-67 f-21 CN ch3 HN〇2 S03H HH 1-68 f-21 CN ch3 S03H OH N〇2 HH 1-69 f-21 CN cf3 N〇2 H S03H ch3 H 1-70 f-21 CONH2 ch3 H N02 S03H H CN 1-71 f-21 H cf3 S03H CH2OCH3 N〇2 HH 1-72 f -21 CONH2 ch3 N〇2 H S03H OCH3 H -13- 158021.doc 201217337 1-73 f-21 CN ch3 HN〇2 S03H H OH 1-74 f-21 CN cf3 so3H ch3 N〇2 HH 1-75 f -21 conh2 cf3 N〇2 H S03H H CN 1-76 f-24 CN ch3 so3h HN〇2 HH 1-77 f-24 CN ch3 N〇2 H S03H HH 1-78 f-24 CN ch3 HN〇2 S03H HH 1-79 f-24 CN ch3 so3H OH N〇2 HH 1-80 f-24 CN cf3 N〇2 H S03H ch3 H 1-81 f-24 conh2 ch3 HN〇2 S03H H CN 1-82 f-24 H cf3 so3H CH2OCH3 N02 HH 1-83 f-24 conh2 ch3 N〇2 H S03H OCH3 H 1-84 f-24 CN ch3 HN〇2 S03H H OH 1-85 f-24 CN cf3 so3H ch3 N〇2 HH 1 -86 f-24 conh2 cf3 N〇2 H S03H H CN 1-87 f-2 CN ch3 so3h HHN〇2 H 1-88 f-2 conh2 ch3 so3H HHN〇2 H 1-89 f-2 CN cf3 so3H HHN 〇2 H 1-90 f-2 CONH2 cf3 so3H HHN〇2 H 1-91 f-14 CN ch3 so3H HHN〇2 H 1-92 f-14 CONH2 ch3 so3H HHN〇2 H 1-93 f-14 CN cf3 so3H HHN〇2 H 1-94 f-14 CONH2 cf3 so3H HHN〇2 H 1-95 f-21 CN ch3 so3H HHN〇2 H 1-96 f-21 CONH2 ch3 so3H HHN〇2 H 1-97 f-21 CN cf3 so3H HHN〇2 H 1-98 f-21 CONH2 cf3 so3H HHN〇2 H 1-99 f -24 CN ch3 so3H HHN〇2 H 1-100 f-24 CONH2 ch3 so3H HHN〇2 H 1-101 f-24 CN cf3 so3H HHN〇2 H 1-102 f-24 CONH2 cf3 so3H HHN〇2 H Preferred are the compound (1-1) to the compound (1-21), the compound (1-43) to the compound (1-45), the compound (1-54) to the compound (1-56), and the compound (1-65). - Compound (1-67), compound (1-76) to compound (1-78), and compound (1-87) to compound (1-102), more preferably compound (1-43) to compound (1) -44), compound (1-54)~compound (1-55), compound (1-65)~compound (1-66), compound 158021.doc -14-201217337 (1-76)~compound (1) -77), the compound (I_87), the compound (1-91), the compound (1-95), and the compound (1-99), and more preferably a compound (1-43), Compound (1-65), the compound (1-87) and the compound (195). When the compound (I) is such a compound, the molar absorption coefficient tends to be particularly high. The compound of the present invention includes, for example, the following compounds.

In the formula (100), R_1GQ is an alkylcarbonyloxyalkyl group having 1 to 12 carbon atoms which may be substituted with an alkoxycarbonyl group having a carbon number of i to 8, which is a cyano group, and R3(10) is an alkyl group having a carbon number of 4, A compound of the formula (100) wherein R(10) is an alkylcarbonyloxyalkyl group having a carbon number of 1 to 12 which is substituted by an alkoxycarbonyl group of a carbon number of 8 to a cyano group. , R3QQ is a methyl group, a compound of a hydrogen atom or an alkali metal atom; a formula (100) ten' R_ is a calcined oxyalkyl group of a carbon number 12, and r200 is a cyano group R is a carbon number of 1 to 4. a compound in which an alkyl group is a hydrogen atom or an alkali metal atom; in the formula (1〇〇), R1〇() is an alkylcarbonyloxyalkyl group having 1 to 12 carbon atoms, and C is a methyl group. A compound which is a hydrogen atom or a metal atom; R1 in the formula (100). "Alkylcarbonyloxyalkyl group having a carbon number of 1 to 12 substituted with an alkoxy group of carbon number 8, a cyano group of a cyano group, an alkyl group having a carbon number of 1 to 4, and a hydrogen atom; Or a compound of an alkali metal atom, and formula (100) t, R1. . Alkylcarbonyloxyalkyl substituted by alkoxy group of carbon number 8 158021.doc •15- 201217337 1~12, r2gg is cyano, r3gg is methyl, μ is aman atom or A compound of a metal atom. 02N R3<0 R200 N=N—(200) S03h HO Ri〇〇 In the formula (200), R1gg is an alkylcarbonyloxyalkyl group having 1 to 12 carbon atoms which may be substituted by an alkoxycarbonyl group having a carbon number of id. , R 2 〇〇 is a cyano group, R 3 (9) is a carbon number 4 alkyl group, hydrazine is a hydrogen atom or an alkali metal atom; in the formula (200), R 1 GG is substituted by a carbon number 8 alkoxycarbonyl group An alkylcarbonyloxyalkyl group having 1 to 12 carbon atoms, R2 is a cyano group, r is a methyl group, a hydrogen atom or a compound of a metal atom; and in the formula (200), R1(10) is a carbon number 12 alkane a carbonyloxyalkyl group, R 2 〇Q is a cyano group, R 3 GG is an alkyl group having 1 to 4 carbon atoms, and μ is a hydrogen atom or an alkali metal atom; in the formula (200), R 1 (10) is a carbon number 12 alkane a carbonyloxyalkyl group, a compound wherein R 2 (10) is a cyano group, R 3 Q G is a fluorenyl group, and hydrazine is a hydrogen atom or an alkali metal atom; and in the formula (200), R (10) is a carbon substituted with an alkoxycarbonyl group having a carbon number of 丨8. An alkylcarbonyloxyalkyl group having 1 to 12, R· is a cyano group, R 3 Q G is an alkyl group having a carbon number of 4, and hydrazine is a compound of a hydrogen atom or an alkali metal atom; and in the formula (200), R 1 Q G is a Alkoxycarbonyl group having a carbon number of 丨8 Alkylcarbonyloxyalkyl the carbon number of 1~12, r2〇G is cyano, R3⑽ is methyl, M is hydrogen atom or a metal atom of the test compound. The compound of the present invention can be obtained by the method described in Japanese Patent Publication No. Hei 7-88633, that is, the diazonium salt represented by the following formula (a2) and the pyridine represented by the formula (a3) 15802 丨.doc, 201217337. The ketone compound is produced by diazo coupling. The diazonium salt represented by the formula (02) can be obtained, for example, by diazotizing an amine represented by the formula (al) with nitrous acid, nitrite or nitrite.

In the formula (4), the formula (a2), and the formula (a3), r1 to rS each have the same meaning as described above. A1 represents an inorganic anion or an organic anion. Examples of the inorganic anion include a fluoride ion, a chloride ion material, a Wei material, a (4) acid material, and hypochlorous acid. The organic anion is, for example, CH3C〇〇. Che Yijia can list vapor ions, desert ions, CH3C〇〇, and so on. The compound of the present invention can be produced by coupling a diazonium salt represented by the formula (a2) with a hydrazine compound represented by the formula (4)) in an aqueous solution of diazo. The anti-reservoir temperature is preferably -rc~ah', preferably 〇t~3〇w, preferably from 1 hour to 12 hours, more preferably from 1 hour to 4 hours. The above aqueous solvent «1 is exemplified by N-methyl group. Burning ketones than π. The compound of the present invention wherein RrR^?1 is *_〇_c〇- represents a bonding position with L1, that is, a compound represented by formula (Ib)" is sometimes referred to as "compound (Ib)"). The manufacturing method in the case of 15802l.doc 201217337

[In the formula (lb), r2 to r9 and [1 八 2 | ϊ main _ 匕 ^ and L knives are not in the same meaning as described above]. (lb) An azo represented by the formula (b4) can be produced by diazo coupling of a diazonium compound represented by the above formula (a2) and a pyridone compound represented by the following formula (b3) by the same method as described above. Compound.

[In the formulas (10) and (b4), 'R2 to R9 and L1 respectively have the same meanings as the above]. u octagonal can be represented by the azo compound represented by the formula (b4) and R^-CO-Z'R9 in the same meaning as above, and z1 represents a chlorine atom or a bromine atom in the presence of an organic compound. The reaction is carried out to obtain the compound (ib). The reaction temperature is preferably 30 C 180 C 'more preferably 5 〇〇 c 〜 12 (rc. The reaction time is preferably 丄 hour to 12 hours 'more preferably 丄 hour to 4 hours). —: is the above-mentioned organic solvent', and examples thereof include a hydrocarbon solvent such as toluene or diphenylbenzene, a halogenated hydrocarbon solvent such as benzene, dichlorobenzene or gas, a nitrohydrocarbon solvent such as nitrobenzene, and methyl isobutyl ketone. A _ 齐 齐 卜 甲基 甲基 甲基 158 158 158 158 021 021 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 158 Below the ear, it is preferably 4 mol or less above the molar amount. The compound R1 of the present invention is _L1_X1_r9 and the conjugate (1) (* represents a bonding position with L1), that is, a compound represented by the formula (Ic) Hereinafter, a manufacturing method sometimes referred to as "compound (Ie)") will be described.

Knife indicates the same meaning as above. The diazonium 1 represented by the above formula (a2) can be caused by the method of the above-mentioned 楛 I I I think I J Ύ , f + r like the above formula (c3) 咐 * χ α ( C4wfr _ 乂 ° 定 _ compound diazo coupling to produce an azo compound of the formula (C4). [In the formula (1C), R2~R9&amp;L,

An azo compound represented by the formula (C4) and R9_〇H (here, (c3) [formula (6)) and a formula (referred to as meaning). Secondly, by 158021.doc ”9·201217337 R9 The reaction is carried out in the presence of an organic solvent to obtain the compound (Ic). The reaction temperature is preferably from 艺 丨 丨 〇 〇 & , , , , , , , , 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 It is 1 hour to 12 hours, more preferably ^/hour to 4 hours. The organic solvent used herein may be the same as the user of the reaction of the azo compound represented by the formula (b4) and y-co-z1. The solvent is used. The amount of R-OH used is usually 1 mol or more and 8 mol or less, more preferably 4 mol or less per mol of the azo compound shown by the formula (c4). In order to carry out the reaction smoothly, it is preferable to add an acidic catalyst. Examples of the acidic catalyst include inorganic acids such as sulfuric acid and hydrochloric acid, etc. The amount of the catalyst used is arbitrary, but it is relative to R9_〇H. i mole, preferably 0.01 to 4 moles, more preferably 8 to 2 moles. The invention of the invention is obtained as a target compound from the reaction mixture. The method of the compound is not particularly limited, and various known means can be employed. For example, the reaction mixture can be mixed with an acid (for example, acetic acid) and water, and the precipitated crystal can be collected by filtration. The acid is preferably an aqueous solution prepared in advance (10). The hydrazine reaction mixture is added to the above aqueous solution. The temperature at which the reaction mixture is added is usually 10 ° C or more and 50 ° C or less, preferably 2 〇〇 c or more and 5 or less (rc or less, more preferably C, and above 3 0 C). Preferably, after the reaction mixture is added to the aqueous acid solution, the mixture is stirred at the same temperature for about 5 to 2 hours. The crystals collected by filtration are preferably washed with water or the like, and then dried. Purification is carried out by a known means such as recrystallization. The compound of the present invention is useful as a dye. 158021.doc 201217337 The compound as an active ingredient

The dye of the present invention is a color filter of a display device such as a crystal display device having a higher solubility in a dyeing agent of the present invention. The colored photosensitive resin composition of the present invention contains the t dye of the present invention as a dye. A coloring agent (hereinafter sometimes referred to as "coloring agent (A)") further contains a resin (B) and a solvent (E). The colored photosensitive resin composition of the present invention preferably further contains a polymerizable compound (C) and a polymerization initiator (D). The colored photosensitive resin composition of the present invention can be used in various types such as a display device (for example, a liquid crystal display device and an organic EL device) having a color light-passing sheet as a component thereof, and a solid-state image sensor. Image related to the machine. The colorant (A) may further contain, in addition to the dye of the present invention, 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, a Colour Index (published by The Society of Dyers and Colourists) can be cited as "Solvent, Acid, Basic, Reactive". (Reactive), Direct, Disperse, or Vat dyes. More specifically, the following color index (C.I.) numbered dyes may be mentioned, but are not limited thereto. CI Solvent Yellow 25,79,81,82,83,89 ; 158021.doc •21· 201217337 CI Acid Yellow 7,23, 25, 42, 65, 76,· CI Reactive Yellow 2,76,116 ; CI Direct Yellow 4 ' 28 ' 44,%,132 ; CI disperse yellow 54,76 ; CI: Solvent orange 41,54,56,99 ; CI acid dial 56, 74' 95, i〇8, 149, i62; CI reactivity Orange 16; CI Direct Orange 26; C · I. "Valley Red 2 4 ' 4 9,9 0,91 127 , 130 ' 132 , l60 , 218 CI Acid Red 73,91,92,97 CI Acid Violet i〇 2; CI Solvent Green 1,5; 118, 119, 122, 124, 125, 138, 151, 211, 274, 289; C. I · Acid Green 3,5,9,2 5,2 8 C. I · Verinatory green 1; CI reduced green 1 and so on. The pigment 'is an organic pigment or ''', which is usually used for a pigment dispersion resist, and an organic pigment. Examples of the inorganic pigment include a metal compound such as a metal oxide or a metal salt, and specific examples thereof include oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, and rhodium. Or a composite metal oxide. Further, as the organic pigment and the inorganic pigment, specifically, a compound classified as a pigment (Pigment) in the Colour Index (published by The Society of Dyers and Colourists) can be cited. More specifically, the color index (C.I.) numbering pigments such as 158021.doc •11 and 201217337 may be cited, but are 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 tests 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, 47, and 58 etc. 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 means a total of components other than the solvent in the colored photosensitive resin composition. The content of the dye of the present invention contained in the colorant (A) t is preferably from 3 to 1% 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 (B) is preferably an alkali-soluble resin, more preferably a resin containing a structural unit derived from (meth)acrylic acid. Here, (meth)acrylic acid means acrylic acid and/or methacrylic acid. Specific examples of the resin (Β) include a methacrylic acid/phenyl methacrylate styrene copolymer, methacrylic acid/phenyl methacrylate/styrene copolymer 158021.doc •23-201217337, methacrylic acid/ Phenyl methacrylate / isodecyl methacrylate copolymer, methacrylic acid / styrene / phenyl methacrylate / N_phenyl maleimide copolymer, methacrylic acid / styrene / methyl propyl Dilute glycidyl ester copolymer and the like. The weight average molecular weight of the tree (B) converted by the polyethylene is preferably 5,000 to 35,000, more preferably 6,000 to 30, 〇〇〇. The acid value of the resin (B) is preferably from 50 to 150, more preferably from 6 to 135. The content of the resin (B) is usually 7 to 65 masses with respect to the solid content of the colored photosensitive resin composition. /. Preferably, it is ～6〇% by mass. The polymerizable compound (C) is not particularly limited as long as it is a compound which can be polymerized by an active radical, an acid or the like which is produced from the polymerization initiator (D). For example, a polymerizable compound having a carbon-carbon unsaturated bond can be cited. The polymerizable 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 neopentyltetraethylene tetrapropene, neopentyltetrakilyl acrylate, dipentaerythritol, pentane vinegar, and hexaerythritol. Pentaerythritol pentadecyl acrylate acid, dipentaerythritol hexaacrylate vinegar, and dipentaerythritol hexamethyl acrylate vinegar. These photopolymerizable compounds (C) may be used singly or in combination of two or more. The content of the polymerizable compound (C) is preferably from 5 to 65% by mass, more preferably from 1 to 6 % by mass, based on the solid content of the coloring photosensitive resin combination, as the polymerization initiator (D) ' The active radical generator acid generator and the like are listed. The living radical generator produces active radicals by the action of heat or light. Examples of the living radical generating agent include a ketone compound 158021.doc -24·201217337 ketone compound, a thioxanthone compound, and a tri-farming compound '肟 compound. Examples of the above-mentioned alkyl ketone ketone compound include 2-methylmorphinyl-1-(4-methylsulfanylphenyl)propane-1-anthracene, 2-based alkyl-2-indenyl-indole Propane-1-one, benzyldidecyl ketal, 2-hydroxy-2-indenyl-1[4-(2-hydroxyethoxy)phenyl]propan-1-one, and 1-hydroxycyclohexyl Phenyl fluorenone. Examples of the above thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthiaxanone, and 2,4-disulfide. Xanthone and 1- gas-4-propoxythiazepine_. Examples of the above-mentioned three-till compound include 2,4-bis(trimethylsulfonyl)-6-(4-methoxyphenyl)+3,5-tri#, 2,4-bis (trimethylmethyl) )_6•(4)methoxynaphthyl)-1,3'5-three tillage, 2,4-bis(trimethylmethyl)o-methoxystyryl)_1,3,5-tri-,2 ,4-bis(trimethylmethyl)-6-[2-(5-methylbitidine)-N-2-yl) vinyl]-1,3,5-three wells, 2,4-double (three gases Methyl)_6_[2_(吱 _2_2_yl)ethenyl, 2,4-bis(trimethylmethyl)_6_[2_(4-diethylamino-2-methylphenyl)vinyl]- 1'3,5-three tillage, and 2,4•bis(trichloroindenyl)_6_[2_(3,4-dimethoxyphenyl)vinyl]·ns triterpenoid. Examples of the above-mentioned ruthenium compound include a ruthenium-based ruthenium-based compound. Specific examples of the ruthenium compound include benzyl benzhydryl phenyl thiophenyl phenyl) butan-1-one 2 -imine, N-benzoquinone 4-(4-phenyl Thioalkylphenyl)octane ketone: imine, N_acetoxy] puethyl-6-(2-methylbenzhydryl carbazyl-3-yl) And N-acetoxy-K9-ethyl-6]2_methyl_4_(3,3-dimethyl-2,4-dioxos-pentyloxy) benzene f 醯 卡. Further, as the living radical generating agent, for example, 2, M_trimethyl 158021.doc • 25· 201217337 phenyl decyl diphenyl phosphine oxide, 2, 2'-bis(o-chlorophenyl)-4,4,5,5,-tetraphenyl-1,2--biimidazole, 1 〇-butyl-2-chloroacridone, 2-ethyl Anthracene, diphenylethylenedione, 9,10-phenanthrenequinone, camphorquinone, phenylglyoxylate, and dimoxine compound. Examples of the acid generator include 4-hydroxyphenyldimethyl Base p-toluene acid salt, 4-hydroxyphenyl bisindolyl hexafluoroantimonate, 4_ethyl phenyl phenyl dimethyl p-toluene sulfonate, 4 ethoxy phenyl phenyl group Mercapto-benzyl hexafluoroantimonate, Phenyl nickel p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenylsulfonium p-toluenesulfonate, diphenylsulfonium hexafluoroantimonate and other rust salts, nitrobenzyltoluenesulfonic acid Salt and benzoin tosylate. The above polymerization initiator (D) may be used singly or in combination of two or more kinds of the polymerization initiator (D) relative to the resin (B) and the polymerizable compound ( c) 'More preferably 1 to 2% by mass. If 'the sensitivity is increased, the total amount at the time of exposure' is preferably 〇. 1 to 3 〇 mass. /., ^ The content of the polymerization initiator is in the above range It is preferable that the inside of the shell is shortened to improve productivity.

Examples of the solvent (E)' include ether ketone, alcohol, ester, and decylamine.

158021.doc •26- 201217337, alcohol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethyldiethyl ether acetate and diethylene glycol monobutyl ether acetate. Examples of the aromatic hydrocarbons include benzoxylene tris(phenyl). Examples of the above-mentioned A®1 include acetone, 2-top, 2-heptanone, 3-gumamine 4-glyoxime, 4-mercapto-2-cyclopentanone, and 4-pyridyl-4-methyl-2. - cyclopentanone, cyclopentanone and cyclohexyl. Examples of the above alcohols include decyl alcohol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin. Examples of the above hydrazines include ethyl acetate, n-butyl acetate, acenaphthyl sulfonate, amyl formate, isoamyl acetate, isobutyl acetate, dibutyl succinate, isopropyl butyrate, butyric acid. Ethyl ester, butyl butyrate, alkyl ester, decyl lactate, ethyl lactate, butyl lactate, decyl decyl acetate, ethyl methoxyacetate, butyl oxyacetate, cesium ethoxylate Ester, ethoxyacetic acid ethyl acetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, decyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 2曱Methoxy propionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2 - methoxy-2-mercaptopropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl acetonate, methyl acetate, Ethyl acetate, 3-methoxybutyl acetate, 3-mercapto-3-methoxybutyl acetate and γ-butyrolactone. Examples of the above decylamine include hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimercaptoacetamide, and fluorenyl-fluorenyl η. These solvents may be used singly or in combination of two or more. 158021.doc -27-201217337 The content of the solvent (E) in the colored photosensitive resin composition is preferably 70 to 95% by mass or more preferably 75 to 9% by mass based on the coloring photosensitive resin composition. The color photosensitive resin composition of the present invention may optionally contain various additives such as an interfacial activity agent, a filler, and other polymer compound 'adhesion promoter, antioxidant, ultraviolet absorber, light stabilizer, and chain transfer agent. [Embodiment] EXAMPLES Hereinafter, the present invention will be more specifically described by way of examples. In the examples and comparative examples, the % and the parts indicating the content or the amount used are based on the mass basis unless otherwise specified. The structure of the compound was confirmed by magnetic resonance (NMr, nuelear magnetic resonace) (JMM-ECA-500; manufactured by Nippon Denshi Co., Ltd.) in the following examples. Example 1 After adding 246 to 24.6 parts of sodium 4-nitroaniline-2-sulfonate (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.51 parts of sodium hydroxide was added and dissolved. 21.2 parts of sodium nitrite was added under ice cooling, and then 64.1 parts of 35% hydrochloric acid was added in small portions and dissolved, and the mixture was stirred for 2 hours to obtain a suspension containing a heavy gas salt. On the other hand, 26.0 parts of ethyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 20.8 parts of methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), and 2-aminoethanol (Wako Pure Chemical Industries Co., Ltd.) 24.4 parts of the mixture was made and stirred at 95 ° C for 24 hours. The reaction solution was cooled to 1580.doc -28 to 201217337, and was added to a mixture of 3 parts of water and 3 parts of 35% hydrochloric acid, and was stirred at room temperature for 1 hour. The precipitated crystals were obtained as a residue obtained by suction filtration, and then dried to obtain 4 parts of the compound represented by the formula (d1). H&lt;sC ΠΝ

Then, 18.9 parts of the compound represented by the formula (d1) was suspended in 378 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. Here, the suspension containing the above diazonium salt was added dropwise by a pump for 15 minutes. After the completion of the dropwise addition, the dropping was further carried out for 3 minutes, thereby obtaining a yellow suspension. Search for 1 hour. The yellow solid obtained by filtration was dried under reduced pressure at 60 ° C to obtain 43.4 parts of the compound of formula (d2).

H3C CN

&lt;Identification of the compound of the formula (d2)&gt; 'H-NMR (DMSO-d6): 2.54 (3H), 4.14 (2H), 4.26 (2H), 5 23 (1H), 8.00 (1H), 8.21 (1H), 8.44 (1H), 15.08 (1H) Add 7.39 parts of the compound represented by the formula (d3) to the compound 1〇·0 part of the formula (d2) at 70° (:1) The solvent of ^-methylpyrrolidone was given for 3 hours. After the completion of the reaction, the obtained mixture was added to water, and the precipitated crystal was obtained as a residue of the filtration of 158021.doc • 29-201217337, and then dried to obtain a formula. 12.0 parts of the compound shown. The structure was confirmed by iH_NMR.

ciY^^oc2h5 〇2n (d3) &lt;Identification of the compound represented by formula (1-43)&gt; ^-NMR (DMSO-d6): ι.ι〇(3H), 2.49 (2H), 2.49 (2H ), 2.56 (3H), 3.96 (2H), 4.10 (2H), 4.23 (2H), 8.04 (1H), 8.26 (1H), 8.45 (1H), 11.77 (1H), 15.52 (1H) 'Example 2 2.31 parts of the compound of the following formula (d4) was added to 2 parts of the compound represented by the above formula (d2), and stirred at 7 (rC in a solvent of n-methylpyrrolidone for 3 hours). The obtained mixture was added to water and evacuated, and the precipitated crystal was precipitated, and dried to obtain 11.3 parts of the compound of the formula (1-65). The structure was confirmed by lH-NMR.

Η3ς^3Ν

Q2N—^2^N=N—^)=〇S03H HO' \-^, 0 (1-65) &lt;Identification of the compound represented by formula (1-65)&gt; i-NMR (DMS0-d6) : 0.75 (3H), 0.77 (3H), 1.08 (2H), 1.18 -30- 15802l.doc 201217337 (2H), 1.37 (2H), 1.42 (2H), 2.16 (1H), 2.55 (3H), 4.11 ( 2H), 4.23 (2H), 8.03 (1H), 8.27 (1H), 8.47 (1H), 11.61 (lH)! 15.03 (1H) Example 3 in sodium 5-nitroaniline-2-sulfonate 24_8 parts After adding 25 parts of water, 4.55 parts of sodium hydroxide was added and dissolved. Sodium nitrite was added under ice cooling, and then 64 6 parts of 35% hydrochloric acid was added in small portions and dissolved, and stirred for 2 hours to obtain a suspension containing a diazonium salt. On the other hand, 26.0 parts of ethyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 20.8 parts of methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), and 2-aminoethanol (Wako Pure Chemical Industries Co., Ltd.) 24.4 parts of the mixture was made and stirred at 95t: for 24 hours. After cooling the reaction mixture to room temperature, it was added to a mixture of 304 parts of water and 35 parts of 35% hydrochloric acid, and the mixture was stirred at room temperature for 1 hour. The precipitated crystals were obtained as a residue obtained by suction filtration, and then dried to obtain 4 parts of the compound represented by the formula (d1). Then, 18 parts of the compound represented by the formula (d1) was suspended in 38 parts of water, and the pH was adjusted to 9.0 using sodium hydroxide. Here, the suspension containing the above diazonium salt was added dropwise using a pump for 15 minutes. After the completion of the dropwise addition, the mixture was further stirred for 1 minute, whereby a yellow suspension was obtained. Stir for 1 hour. The yellow solid obtained by filtration was dried under reduced pressure at 60 ° C to obtain a compound of formula (d5): 43 parts. 158021.doc -31 - 201217337

&lt;Identification of the compound of the formula (d5)&gt; • H-NMR (DMSO-d6): 2.53 (3H), 4.15 (2H), 4.24 (2H)s 5.23 (1H), 7.82 (1H), 8.01 (1H), 8.40 (1H), l5 〇7 (1H), 7.30 parts of the compound represented by the formula (d3) are added to 10.0 parts of the compound represented by the formula (d5), and each of the ketones is N under the thief. When giving a drop in the solvent. After the completion of the reaction, the obtained mixture was added to water, and the precipitated crystals were obtained as a residue by suction filtration, and dried to obtain 11.9 parts of the compound of the formula (1·1). The structure was confirmed by h-NMR.

&lt;Identification of the compound of the formula (1-87)&gt; ^-NMR (DMSO-d6): 1.10 (3H), 2.49 (2H), 2.49 (2H), 2.56 (3H), 3.96 (2H), 4.10 (2H), 4.23 (2H), 7.82 (1H), 8·01 (1H) 8.40 (1Η), 11.70 (1Η), 15.52 (1Η) Example 4 Compound 2 shown in the above formula (d5)〇 - 2.34 parts of the compound of the above formula (d4) was added to the residue, and the mixture was stirred at 70 ° C in a solvent of N-methylpyrrolidone 158021.doc -32 - 201217337 for 3 hours. After the completion of the reaction, the obtained mixture was added to water, and the precipitated crystal was obtained as a residue obtained by suction filtration, followed by drying to obtain a compound portion 11 &gt; 2 parts represented by the formula (1-95). The structure was confirmed by iH_NMR.

&lt;Identification of a compound represented by the formula (1-95)&gt; 'H-NMR (DMSO-d6): 〇.75 (3H), 0.77 (3H), l.〇g (2H)5 i.ig ( 2H), 1.37 (2H), 1.42 (2H), 2.16 (1H), 2.55 (3H), 4.11 (2H), 4.23 (2H), 7.85 (1H), 8.10 (1H), 8.35 (1H)} n. 8〇(m)&gt; 15.03 (1H) 'Comparative Example 1 The compound represented by the formula (i) was obtained by the method described in JP-A No. 53977.

[Measurement of absorption spectrum] 158021.doc -33-201217337 The absorption spectra of the compounds obtained in Examples 1 to 4 and Comparative Example 1 were measured in the following manner. 0.10 g of the compound was dissolved in dimercaptocaramine to make the volume 250 cm3, and 2 cm3 of the solution was diluted with ethyl lactate to make the volume 100 cm3 (concentration: 0.0080 g/L), using an ultraviolet-visible spectrophotometer. (V-65 0DS; manufactured by Sakamoto Seiki Co., Ltd.) (quartz cuvette, optical path length; 1 cm) The absorption spectrum was measured. The results are shown in Table 2. Table 2 Maximum absorption wavelength of compound (nm) Molar absorption coefficient Example 1 1-43 436 49300 Example 2 1-65 436 49300 Example 3 1-87 426 48300 Example 4 1-95 426 48500 Comparative Example 1 i 431 32300 [Evaluation of Solubility] The compounds obtained in Examples 1 to 4 and Comparative Example 1 were obtained in the following manner for N-mercaptopyrrolidone (hereinafter abbreviated as NMP) and N,N'-didecylguanamine. (Slightly DMF below) solubility. In a 50 mL sample tube, 0.03 g of the compound was mixed with 1 g of the above solvent, and then the sample tube was stoppered and shaken at 30 ° C for 3 minutes using an ultrasonic vibration machine. Then, it was allowed to stand at room temperature for 30 minutes, and then filtered to visually observe the residue. When the insoluble matter as the residue was not confirmed, it was judged that the solubility was good, and it was recorded as 〇 in Table 2, and when it was confirmed that there was an insoluble matter, it was judged that the solubility was poor, and it was referred to as X in Table 2. The results are shown in Table 3. 158021.doc •34· 201217337 Table 3

Compound NMP DMF Example 1 1-43 〇〇 Example 2 1-65 〇〇 Example 3 1-87 〇〇 Example 4 1-95 6 〇 Comparative Example 1 i XX Example 5 [Coloring photosensitive resin composition Preparation] The following materials were mixed to obtain a colored photosensitive resin composition: (A) Colorant: Compound (Ι·43): Compound synthesized in Example 1 20 parts (Β-1) Resin: methacrylic acid/ Benzyl methacrylate copolymer (molar ratio 30/70 'weight average molecular weight is 1〇7〇〇, acid value is 7〇mgK〇H/g) 50 parts (C-1) polymerizable compound) Dipentaerythritol hexaacrylate (50 parts of Nippon Kayaku Co., Ltd.)

(D-1) Polymerization initiator: Irgacure OXE01 (肟 compound; BASF 15 parts 680 parts).

(manufactured by Japan) (E-1) Solvent: ν, Ν·-dimethyl decylamine Example 6 [Preparation of colored photosensitive resin composition] The following materials were mixed to obtain a colored photosensitive resin composition: Colorant: Compound (1-65): Compound synthesized in Example 2 20 parts (Β-1) Resin: methacrylic acid/phenyl methacrylate copolymer (Mo Erbi is 158021.doc -35- 201217337 30/70 'Weight average molecular weight is 10700, acid value is 70 mgKOH/g) 50 parts (C-1) Polymerizable compound: Dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D- 1) Polymerization initiator: irgacure 〇χΕ01 (肟 compound; manufactured by BASF Japan Co., Ltd.) 15 parts (E-1) solvent: 680 parts of N,N'-dimethyl decylamine. Example 7 [Preparation of Colored Photosensitive Resin Composition] The following materials were mixed to obtain a colored photosensitive resin composition: (A) Colorant: Compound (Io 87): 20 parts of the compound synthesized in Example 3 (B- 1) Resin: methacrylic acid/phenyl methacrylate copolymer (molar ratio 30/70 'weight average molecular weight is 1〇7〇0, acid value 70 mgKOH/g) 50 parts (C-1) polymerizability Compound: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 50 parts» (D-1) polymerization initiator: ilgacure οχΕΟΙ (fat compound; manufactured by BASF Japan) 15 parts (E-1) solvent: Ν, Ν·_ dimethyl decylamine 680 parts Example 8 [Preparation of colored photosensitive resin composition] The following materials were mixed to obtain a colored photosensitive resin composition: (Α) Colorant: Compound (1_95) : Compound synthesized in Example 4 158021.doc • 36- 201217337 20 parts (B-1) Resin: mercapto acrylate/methacrylic acid stupid ester copolymer (mole ratio 30/70, weight average molecular weight 10700, Acid value: 70 mgKOH/g) (C-1) Polymeric compound: dipentaerythritol hexaacrylate (Japanese) Manufacturing Corporation) 50 parts (D-1) a polymerization initiator: Irgacure OXE01 (oxime compound; BASF Japan Ltd.) 15 parts (E-1) Solvent: NW- dimethyl Yue Amides 680 parts. [Production of Color Filter] The above-described colored photosensitive resin composition was applied onto glass by a spin coating method to volatilize volatile components. After cooling, light irradiation was performed using a patterned quartz glass mask and an exposure machine. After light irradiation, it was developed with an aqueous solution of potassium hydroxide and heated in an oven to 2 Torr to obtain a color light-emitting sheet. From the results of Table 2, it was found that the compounds of the examples had a large molar absorption coefficient. Further, according to the results of Table 3, it was found that the organic solvent showed high solubility. Therefore, it can be said that it is useful as a dye used for a color light-emitting sheet of a display device. [Industrial Applicability] The compound of the present invention is useful as a dye contained in a photo-resin composition because it has a large coefficient of A, and has a large coefficient. 158021.doc -37-

Claims (1)

201217337 VII. Scope of application: 1. A compound represented by formula (I): R7 R8 HO', r1 RwR4 rwr2 [In the formula (I), R1 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms] The _CH2_ contained in the aliphatic hydrocarbon group may also be via _〇_ or _C0_substituted; R represents a hydrogen atom, a cyano group or an aminomethyl group; R3 represents an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted by a south atom; R~R8 are mutually Independently, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, 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 or -S〇3M, At least R4~R8! One represents a nitro group, and at least i represents -S03M; Μ represents a hydrogen atom or an alkali metal atom]. 2. For the compound of claim 1, which is represented by the formula: R? R2 S03M H0 R1 [In the formula (II), ri, r2, r3 R and M respectively have the same meanings as described above]. 3. The compound of the claim, wherein r^_l1_x1r9. 158021.doc 201217337 [L1 represents a carbon number of 1 to 8 alkanediyl; X1 represents -CO-O-; R9 represents a gas atom or a carbon number of 1 to 17 The valence aliphatic hydrocarbon group may be substituted by -CH2- or -CO- contained in the aliphatic radical; wherein 'L1, χΐ and the carbon number thereof are 20 or less in total]. 4. The compound of claim 3, wherein X1 is *-0-C0-, [* represents a bond to L1]. A dye according to any one of claims 1 to 4 as an active ingredient. 6. A colored photosensitive resin composition which comprises a compound as claimed in the claims, a resin, and a solvent. 158021.doc -2- 201217337 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 display. Chemical formula of the inventive feature: 158021.doc