CN102108061A - Pyridone compound - Google Patents

Pyridone compound Download PDF

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Publication number
CN102108061A
CN102108061A CN2010106206391A CN201010620639A CN102108061A CN 102108061 A CN102108061 A CN 102108061A CN 2010106206391 A CN2010106206391 A CN 2010106206391A CN 201010620639 A CN201010620639 A CN 201010620639A CN 102108061 A CN102108061 A CN 102108061A
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China
Prior art keywords
compound
methyl
carbonatoms
butyl
ethyl
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芦田徹
辰巳泰基
朴昭妍
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
    • C09B35/18—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from heterocyclic compounds
    • C09B35/185—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from heterocyclic compounds from pyridine or pyridone components

Abstract

The invention discloses a pyridone compound, a dye with the pyridine compound as the active ingredient and a colored resin composition comprising the dye with the pyridine compound as the active ingredient, resin and a solvent.

Description

Pyridinone compounds
Technical field
The present invention relates to be used for the compound of dyestuff.
Background technology
Dyestuff is used for for example, and fields such as filamentary material, liquid crystal indicator, ink-jet utilize reflected light or transmitted light to develop the color.
For example, record the compound that following formula is represented among the embodiment 1 of patent documentation 1.
Figure BSA00000407748900011
[patent documentation 1] Japanese Patent spy opens 2004-2630
Summary of the invention
Existing compound, its molar absorptivity is little, divides optical concentration very not satisfactory.
The invention provides following [1]～[5].
[1] compound of formula (I) expression.
Figure BSA00000407748900012
In the formula (I), R 1Alkyl, the aryl of carbonatoms 6～21 or the aralkyl of carbonatoms 7～21 of expression carbonatoms 1～8;
R 2Expression hydrogen atom, cyano group or formamyl;
R 3The alkyl or the trifluoromethyl of expression carbonatoms 1～4;
R 4～R 7Represent the alkyl of hydrogen atom, carbonatoms 1～8, the alkoxyl group of carbonatoms 1～8, alkoxyalkyl, hydroxyl, cyano group or the nitro of carbonatoms 2～8 independently of each other, R 4～R 7In have at least one the expression nitro.]
[2] compound of above-mentioned [1] record, R 5Perhaps R 6Be nitro.
[3] compound of above-mentioned [1] or [2] record, R 2Be cyano group.
[4] more than one compounds of stating any record in [1]～[3] are the dyestuff of effective constituent.
[5] a kind of colored resin composition that contains dyestuff, resin and the solvent of above-mentioned [4] record.
Embodiment
The present invention is the represented compound of formula (I) (below, also claim compound (I)).Compound of the present invention also comprises its tautomer.
Figure BSA00000407748900021
In the formula (I), R 1Alkyl, the aryl of carbonatoms 6～21 or the aralkyl of carbonatoms 7～21 of expression carbonatoms 1～8;
R 2Expression hydrogen atom, cyano group or formamyl;
R 3The alkyl or the trifluoromethyl of expression carbonatoms 1～4;
R 4～R 7Represent the alkyl of hydrogen atom, carbonatoms 1～8, the alkoxyl group of carbonatoms 1～8, alkoxyalkyl, hydroxyl, cyano group or the nitro of carbonatoms 2～8 independently of each other, wherein have an expression nitro at least.
In the formula (I), R 1Alkyl, the aryl of carbonatoms 6～21 or the aralkyl of carbonatoms 7～21 of expression carbonatoms 1～8.
The alkyl of carbonatoms 1～8 can have for example, for example straight chained alkyls such as methyl, ethyl, n-propyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl;
Sec.-propyl, isobutyl-, sec-butyl, isopentyl, the 1-methyl amyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1-methyl hexyl, 2-methyl hexyl, 3-methyl hexyl, 4-methyl hexyl, 5-methyl hexyl, the 1-ethyl pentyl group, the 2-ethyl pentyl group, the 3-ethyl pentyl group, 1-propyl group butyl, 1-(1-methylethyl) butyl, 1-(1-methylethyl)-2-methyl-propyl, the 1-methylheptyl, the 2-methylheptyl, the 3-methylheptyl, the 4-methylheptyl, the 5-methylheptyl, the 6-methylheptyl, the 1-ethylhexyl, the 2-ethylhexyl, the 3-ethylhexyl, the 4-ethylhexyl, 1-n-propyl amyl group, 2-propyl group amyl group, 1-(1-methylethyl) amyl group, 1-butyl butyl, 1-butyl-2-methyl butyl, 1-butyl-3-methyl butyl, 1-(1, the 1-dimethyl ethyl) butyl butyl, the tertiary butyl, 1, the 1-dimethyl propyl, 1, the 1-dimethylbutyl, 1, the 2-dimethylbutyl, 1, the 3-dimethylbutyl, 2, the 3-dimethylbutyl, 1-ethyl-2-methyl-propyl, 1,1-dimethyl amyl group, 1,2-dimethyl amyl group, 1,3-dimethyl amyl group, 1,4-dimethyl amyl group, 2,2-dimethyl amyl group, 2,3-dimethyl amyl group, 2,4-dimethyl amyl group, 3,3-dimethyl amyl group, 3,4-dimethyl amyl group, 1-ethyl-1-methyl butyl, 1-ethyl-2-methyl butyl, 1-ethyl-3-methyl butyl, 2-ethyl-1-methyl butyl, 2-ethyl-3-methyl butyl, 1,1-dimethyl hexyl, 1,2-dimethyl hexyl, 1,3-dimethyl hexyl, 1,4-dimethyl hexyl, 1,5-dimethyl hexyl, 2,2-dimethyl hexyl, 2,3-dimethyl hexyl, 2,4-dimethyl hexyl, 2,5-dimethyl hexyl, 3,3-dimethyl hexyl, 3,4-dimethyl hexyl, 3,5-dimethyl hexyl, 4,4-dimethyl hexyl, 4,5-dimethyl hexyl, 1-ethyl-2-methyl amyl, 1-ethyl-3-methyl amyl, 1-ethyl-4-methyl amyl, 2-ethyl-1-methyl amyl, 2-ethyl-2-methyl amyl, 2-ethyl-3-methyl amyl, 2-ethyl-4-methyl amyl, 3-ethyl-1-methyl amyl, 3-ethyl-2-methyl amyl, 3-ethyl-3-methyl amyl, 3-ethyl-4-methyl amyl, 1-propyl group-1-methyl butyl, 1-propyl group-2-methyl butyl, 1-propyl group-3-methyl butyl, 1-(1-methylethyl)-1-methyl butyl, 1-(1-methylethyl)-2-methyl butyl, 1-(1-methylethyl)-3-methyl butyl, 1,1-diethyl butyl, 1, branched-chain alkyls such as 2-diethyl butyl.
The aryl of carbonatoms 6～21 can be enumerated, for example phenyl, naphthyl, biphenylene, fluorenyl, anthryl etc., wherein, preferred phenyl.
The aralkyl of carbonatoms 7～21 can be enumerated, for example phenmethyl, Biphenylmethyl, phenylethyl, 3-phenyl propyl etc.
R 1From raw material easily this point of starting with, the alkyl of preferred carbonatoms 1～4, in addition, and from this point of solvability, preferred branched-chain alkyl, more preferably 2-ethylhexyl.
R 2Be hydrogen atom, cyano group or formamyl.Wherein, cyano group is started with easily owing to raw material, more preferably.
R 3The alkyl or the trifluoromethyl of expression carbonatoms 1～4.
The alkyl of carbonatoms 1～4 can have for example, for example methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, the tertiary butyl etc.
R 4～R 7Be the alkyl of hydrogen atom, carbonatoms 1～8, the alkoxyl group of carbonatoms 1～8, alkoxyalkyl, hydroxyl, cyano group or the nitro of carbonatoms 2～8 independently of each other, wherein at least one is a nitro.When compound (I) when having nitro, divide optical concentration that the tendency that uprises is arranged, so preferably.
Wherein, R 5Perhaps R 6Be preferably nitro, further, more preferably R 5Be nitro.When nitro is in these positions, divide optical concentration that the tendency that uprises is arranged, so preferred.
The alkyl of carbonatoms 1～8 can be enumerated alkyl same as described above.
The alkoxyl group of carbonatoms 1～8 can have been enumerated, for example methoxyl group, oxyethyl group, propoxy-, butoxy, pentyloxy, hexyloxy, heptan oxygen base, octyloxy, 2-ethyl hexyl oxy etc.
The alkoxyalkyl of carbonatoms 2～8 can have been enumerated, for example methoxyl methyl, methoxyethyl, methoxycarbonyl propyl, methoxy butyl, methoxy amyl group, 1-ethoxycarbonyl propyl, 2-ethoxycarbonyl propyl, 1-oxyethyl group-1-methylethyl, 1-methyl-2-ethoxyethyl group, 1-(1-methyl ethoxy) propyl group, 2-(1-methyl ethoxy) propyl group, 1-(1-methyl ethoxy)-1-methylethyl, 2-(1-methyl ethoxy)-1-methylethyl, 3-ethoxycarbonyl propyl etc.
Compound (I) can be enumerated, for example compound shown in compound (I-1)～compound (I-50) etc.In the table 1, C 4H 9(n) expression normal-butyl.
Figure BSA00000407748900041
[table 1]
Compound R 1 R 2 R 3 R 4 R 5 R 6 R 7
I-1 C 4H 9(n) CN CH 3 H NO 2 H H
I-2 C 4H 9(n) CN CH 3 H H NO 2 H
I-3 C 4H 9(n) CN CH 3 NO 2 H H H
I-4 C 4H 9(n) CN CH 3 H H H NO 2
I-5 C 4H 9(n) CN CH 3 H NO 2 NO 2 H
I-6 C 4H 9(n) CN CH 3 H NO 2 CH 3 H
I-7 C 4H 9(n) CN CH 3 H CH 3 NO 2 H
I-8 C 4H 9(n) CN CH 3 H NO 2 H CH 3
I-9 C 4H 9(n) CN CH 3 CH 3 H NO 2 H
I-10 C 4H 9(n) CN CH 3 H NO 2 H OCH 3
I-11 C 2H 5 CONH 2 CH 3 H NO 2 H H
I-12 C 2H 5 CONH 2 CH 3 H H NO 2 H
I-13 C 2H 5 CONH 2 CH 3 NO 2 H H H
I-14 C 2H 5 CONH 2 CH 3 H H H NO 2
I-15 C 2H 5 CONH 2 CH 3 H NO 2 NO 2 H
I-16 C 2H 5 CONH 2 CH 3 H NO 2 CH 3 H
I-17 C 2H 5 CONH 2 CH 3 H CH 3 NO 2 H
I-18 C 2H 5 CONH 2 CH 3 H NO 2 H CH 3
I-19 C 2H 5 CONH 2 CH 3 CH 3 H NO 2 H
I-20 C 2H 5 CONH 2 CH 3 H NO 2 H OCH 3
I-21 C 2H 5 CN CH 3 H NO 2 H H
I-22 C 2H 5 CN CH 3 H H NO 2 H
I-23 C 2H 5 CN CH 3 NO 2 H H H
I-24 C 2H 5 CN CH 3 H H H NO 2
I-25 C 2H 5 CN CH 3 H NO 2 NO 2 H
I-26 C 2H 5 CN CH 3 H NO 2 CH 3 H
I-27 C 2H 5 CN CH 3 H CH 3 NO 2 H
I-28 C 2H 5 CN CH 3 H NO 2 H CH 3
I-29 C 2H 5 CN CH 3 CH 3 H NO 2 H
I-30 C 2H 5 CN CH 3 H NO 2 H OCH 3
I-31 C 4H 9(n) H CH 3 H NO 2 H H
I-32 C 4H 9(n) H CH 3 H H NO 2 H
I-33 C 4H 9(n) H CH 3 NO 2 H H H
I-34 C 4H 9(n) H CH 3 H H H NO 2
I-35 C 4H 9(n) H CH 3 H NO 2 NO 2 H
I-36 C 4H 9(n) H CH 3 H NO 2 CH 3 H
I-37 C 4H 9(n) H CH 3 H CH 3 NO 2 H
I-38 C 4H 9(n) H CH 3 H NO 2 H CH 3
I-39 C 4H 9(n) H CH 3 CH 3 H NO 2 H
I-40 C 4H 9(n) H CH 3 H NO 2 H OCH 3
I-41 C 4H 9(n) CN CF 3 H NO 2 H H
I-42 C 4H 9(n) CN CF 3 H H NO 2 H
Wherein, preferred compound (I-1) and compound (I-11).
These compounds have the high tendency of branch optical concentration, so preferred.
Compound (I) can be made by diazonium salt and pyridinone compounds generation diazo coupling reaction according to the method for the special fair 7-88633 communique record of Japanese Patent.
Particularly, the diazonium salt of compound (I) shown in can through type (b) and the pyridinone compounds generation diazo coupling reaction shown in the formula (c) are made.Diazonium salt shown in the formula (b) can pass through, and for example the amine shown in the formula (a) carries out diazotization by nitrous acid, nitrite or nitrous acid ester and obtains.
Figure BSA00000407748900061
[in formula (a), formula (b) and the formula (c), R 1～R 7With represented same meaning in the formula (I).A 1Represent inorganic or organic anion.]
Above-mentioned inorganic anion can be enumerated, for example fluoride ion, chloride ion, bromide ion, iodide ion, mistake chlorate ions, hypochlorite ion etc.Above-mentioned organic anion can have been enumerated, for example CH 3COO -, C 6H 5COO -Deng.Preferred chloride ion, bromide ion, CH 3COO -Deng.
Pyridinone compounds shown in diazonium salt shown in the through type (b) and the formula (c) reacts in aqueous solvent, can make compound (I).Preferred-5 ℃～60 ℃ of temperature of reaction, more preferably 0 ℃～30 ℃.Preferred 1 hour～12 hours of reaction times, more preferably 1 hour～4 hours.Above-mentioned aqueous solvent can be enumerated, for example N-Methyl pyrrolidone etc.
The method of obtaining the compound (I) of target compound from reaction mixture is not particularly limited, and can adopt various known method.For example, comparatively ideal have, and reaction mixture is mixed the crystal that leaching is separated out with acid (for example acetic acid etc.) and water.For above-mentioned acid, preferably be modulated into aqueous acid in advance, again reaction mixture is added in this aqueous solution.Temperature when adding reaction mixture is generally more than 10 ℃ below 50 ℃, and is preferred more than 20 ℃ below 50 ℃, more preferably more than 20 ℃ below 30 ℃.In addition, add to reaction mixture in the aqueous acid after, be preferably in and synthermally stirred about 0.5～2 hour down.The best waters of crystal of leaching etc. are cleaned, and then carry out drying.In addition, as required, can also use known method such as recrystallization further to purify.
In view of the above, the compound of the present invention of acquisition is that compound (I) can be used as the dyestuff use.Especially since its minute the optical concentration height, utilize reflected light or transmitted light to develop the color, use as dyestuff so can be applied to the colour filter or the filamentary material of display unit such as liquid crystal indicator.
Dyestuff of the present invention is to be the dyestuff of effective constituent with compound of the present invention (I).Colored resin composition of the present invention contains dyestuff of the present invention as tinting material (following also claim " tinting material (A) "), further also contains resin (B) and solvent (E).Colored resin composition of the present invention preferably further also contains polymerizable compound (C) and polymerization starter (D).
Tinting material (A) can also contain pigment and/or the dyestuff different with dyestuff of the present invention except dyestuff of the present invention.
The dyestuffs different with dyestuff of the present invention have been enumerated, and are categorized as the dyestuff of solvent (Solvent), acid (Acid), alkalescence (Basic), active (Reactive), directly (Direct), dispersion (Disperse) or reduction (Vat) etc. in the Colour Index (Colour Index) (The Society of Dyers and Colourists publication).More specifically, can enumerate the dyestuff of following Colour Index (C.I.) sequence number, but be not limited to this.
C.I. solvent yellow 25,79, and 81,82,83,89;
C.I. turmeric yellow 7,23, and 25,42,65,76;
C.I. reactive yellow 2,76, and 116;
C.I. direct yellow 4,28,44,86,132;
C.I. DISPERSE YELLOW 54,76;
C.I. the solvent orange 41,54, and 56,99;
C.I. von Muller's indicator 56,74, and 95,108,149,162;
C.I. reactive orange 16;
C.I. direct orange 26;
C.I. solvent red 24,49,90,91,118,119,122,124,125,127,130,132,160,218;
C.I. Xylene Red 73,91, and 92,97,138,151,211,274,289;
C.I. acid violet 102;
C.I. solvent green 1,5;
C.I. acid green 3,5,9,25,28;
C.I. alkali green 1;
C.I. Vat green 1 etc.
Pigment can be enumerated, and is generally used for the pigment dyestuff or the mineral dye of colo(u)rant dispersion resist.Mineral dye can be enumerated, and the metallic compound of metal oxide or metallic complex salt class can be enumerated metal oxide or complex metal oxidess such as iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony particularly.
In addition,, can enumerate particularly, be classified as the compound of pigment (Pigment) in the Colour Index (Colour Inde x) (The Society of Dyers and Colourists publication) as pigment dyestuff and mineral dye.More specifically, can enumerate the pigment of following Colour Index (C.I.) sequence number, but be not limited to this.
C.I. Pigment Yellow 73 20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,148,150,153,154,166,173 and 180;
C.I. pigment Orange 13,31,36,38,40,42,43,51,55,59,61,64,65 and 71;
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,215,216,224,242,254,255 and 264;
C.I. pigment violet 14,19,23,29,32,33,36,37 and 38;
C.I. pigment Green 7,10,15,25,36,47 and 58 etc.
The content of tinting material (A) is preferably 5～60 quality % with respect to the solids component in the colored resin composition.Herein, solids component is meant the total of the composition outside desolventizing in the colored resin composition.
The content of the dyestuff of the present invention that contains in the tinting material (A) is preferably 3～100 quality %.
Dyestuff different with dyestuff of the present invention and face material can be distinguished individually or make up more than 2 kinds and also use with dyestuff of the present invention.
Resin (B) is not particularly limited, and can use any resin.Resin (B) preferred bases soluble resin more preferably contains the resin by the structural unit of (methyl) vinylformic acid derivation.Here, (methyl) vinylformic acid is represented vinylformic acid and/or methacrylic acid.
Resin (B) can be enumerated particularly, methacrylic acid/methacrylic acid benzyl ester multipolymer, methacrylic acid/methacrylic acid benzyl ester/styrol copolymer, methacrylic acid/methacrylic acid benzyl ester/isobornyl methacrylate multipolymer, methacrylic acid/styrene/methacrylic acid benzyl ester/N-phenyl maleic anhydride contract imine copolymer, methacrylic acid/styrene/methacrylic acid glycidyl ester copolymer etc.
The polystyrene conversion weight-average molecular weight of resin (B) is preferably 5000～35000, and more preferably 6000～30000.
The acid number of resin (B) is preferably 50～150, and more preferably 60～135.
The content of resin (B) is generally 7～65 quality % with respect to the solids component in the colored resin composition, is preferably 13～60 quality %.
Polymerizable compound (C) promptly is not particularly limited so long as polymeric compounds is carried out in living radical that can be by being produced by polymerization starter (D), acid etc.For example can enumerate, have the compound etc. of the carbon-to-carbon unsaturated bond of polymerizability.
Above-mentioned polymerizable compound (C) preferably has the optical polymerism compound of 3 above polymerizable groups.Optical polymerism compound with the polymerizable group more than 3 can be enumerated, for example pentaerythritol tetracrylate, tetramethylolmethane tetramethyl-acrylate, five vinylformic acid dipentaerythritol ester, Dipentaerythritol pentamethyl-acrylate, dipentaerythritol acrylate, Dipentaerythritol hexamethyl acrylate etc.Described optical polymerism compound (C) can be used singly or in combination of two or more thereof.
The content of polymerizable compound (C) is preferably 5～65 quality % with respect to the solids component of colored resin composition, more preferably 10～60 quality %.
Above-mentioned polymerization starter (D) can exemplify living radical and produce agent, acid producing agent etc.It is that effect by heat or light produces living radical that living radical produces agent.Above-mentioned living radical produces agent can exemplified by alkyl groups benzophenone compound, thioxanthone compound, triazine based compound, oxime compound etc.
Abovementioned alkyl benzophenone compound, for example can enumerate 2-methyl-2-morpholine-1-(4-methylthio group phenyl)-1-acetone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1-[4-(2-hydroxyl-oxethyl) phenyl]-1-acetone, 1-hydroxycyclohexylphenylketone etc.
Above-mentioned thioxanthone compound can be enumerated, for example, and 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-two clopenthixal ketones, 1-chloro-4-propoxy-thioxanthone etc.
Above-mentioned triazine based compound can be enumerated, for example 2, two (the trichloromethyl)-6-(4-p-methoxy-phenyl)-1,3 of 4-, the 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl group naphthyl) of 4--1,3,5-triazines, 2, two (the trichloromethyl)-6-(4-methoxyl-styrene)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(2-(5-methyl furan-2-yl) vinyl)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(2-(furans-2-yl) vinyl)-1,3 of 4-, the 5-triazine, 2, two (the trichloromethyl)-6-(2-(4-diethylamino-2-aminomethyl phenyl) vinyl) of 4--1,3,5-triazines, 2, (2-(3 for two (the trichloromethyl)-6-of 4-, the 4-Dimethoxyphenyl) vinyl)-1,3,5-triazines etc.
Above-mentioned oxime compound can be enumerated for example O-acyl group oxime compound; this concrete example has N-benzoyloxy-1-(4-thiophenyl phenyl) butane-1-ketone-2-imines, N-benzoyloxy-1-(4-phenyl sulfenyl phenyl) octane-1-ketone-2-imines, N-acetoxyl group-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl for example] ethane-1-imines, N-acetoxyl group-1-[9-ethyl-6-{2-methyl-4-(3; 3-dimethyl-2,4-dioxy cyclopentyl-methyl oxygen base) benzoyl }-9H-carbazole-3-yl] ethane-1-imines etc.
In addition; living radical produces agent and can enumerate; for example 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2; 2 '-two (Chloro-O-Phenyl)-4; 4 ', 5,5 '-tetraphenyl-1; 2 '-two imidazoles, 10-butyl-2-chloro-acridine ketone, 2-ethyl-anthraquinone, dibenzoyl, 9,10-phenanthrenequione, camphorquinone, phenyl glyoxalic acid methylester, two cyclopentadiene titanium compounds etc.
Above-mentioned acid producing agent can have for example salt of 4-hydroxyphenyl dimethyl sulfonium tosilate, 4-hydroxyphenyl dimethyl sulfonium hexafluoro antimonate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, 4-acetoxyl group phenyl methyl benzyl sulfonium hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium hexafluoro antimonate, phenylbenzene iodine tosilate, phenylbenzene iodine hexafluoro antimonate etc. for example, or nitrobenzyl tosic acid salt, st-yrax tosic acid salt etc.
Above-mentioned polymerization starter (D) can be used singly or in combination of two or more thereof.
The content of polymerization starter (D) is with respect to total metering of 100 mass parts resins (B) and polymerizable compound (C), preferred 0.1～30 mass parts, more preferably 1～20 mass parts.The content of polymerization starter is in above-mentioned scope the time, because highly sensitiveization, the time shutter shortens, and productivity improves, and is therefore comparatively desirable.
As solvent (E), ethers, aromatic hydrocarbon based, ketone, alcohols, ester class, amides etc. are arranged for example.
Above-mentioned ethers can be enumerated, for example, tetrahydrofuran (THF), tetrahydropyrans, 1, the 4-diox, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethylmethyl ether, the Diethylene Glycol dipropyl ether, dibutyl ethylene glycol ether, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, the propylene glycol monopropyl ether acetic ester, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, the diethylene glycol monoethyl ether acetic ester, butyl carbitol acetate etc.
Described aromatic hydrocarbon based can enumerating, for example benzene,toluene,xylene, mesitylene etc.
Can enumerate as ketone, for example acetone, 2-butanone, 2-heptanone, 3-heptanone, dipropyl ketone, 4-methyl-2 pentanone, 4-hydroxy-4-methyl-2 pentanone, cyclopentanone, pimelinketone etc.
As alcohols, can enumerate, for example methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, hexalin, ethylene glycol, glycerine etc.
Above-mentioned ester class can be enumerated, for example vinyl acetic monomer, n-butyl acetate, isobutyl acetate, the formic acid pentyl ester, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, n-Butyl lactate, methoxy menthyl acetate, the Methoxy acetic acid ethyl ester, the Methoxy acetic acid butyl ester, ethoxy acetate, the oxyethyl group vinyl acetic monomer, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, 2-methoxypropionic acid methyl esters, 2-methoxy propyl acetoacetic ester, 2-methoxy propyl propyl propionate, 2-ethoxy-propionic acid methyl esters, the 2-ethoxyl ethyl propionate, 2-methoxyl group-2 Methylpropionic acid methyl esters, 2-oxyethyl group-2 Methylpropionic acid ethyl ester, Pyruvic Acid Methyl ester, Pyruvic Acid Ethyl ester, Propyl pyruvate, methyl acetoacetate, ethyl 3-oxobutanoate, acetate-3-methoxyl group butyl ester, acetate-3-methyl-3-methoxyl group butyl ester, gamma-butyrolactone etc.
Above-mentioned amides can exemplify, N for example, dinethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone etc.
These solvents can be used singly or two or more kinds in combination.
The content of solvent in the colored resin composition (E) is with respect to colored resin composition, preferred 70～95 quality %, more preferably 75～90 quality %.
Colored resin composition of the present invention as required, can also add various additives such as tensio-active agent, filler, other macromolecular compounds, short tackiness agent, antioxidant, UV light absorber, photostabilizer, chain-transfer agent.
Compound of the present invention can be used as dyestuff and uses.Compound of the present invention because the molar absorptivity height, divides the optical concentration height, so for example can be applied to, use as dyestuff in the colour filter of display unit such as liquid crystal indicator.
In addition, the colored resin composition that contains The compounds of this invention, can be applied to have colour filter as in the various machines related such as the display unit (for example, known liquid crystal indicator, organic El device etc.) of its a part of component parts, solid-state imager with known state with rendered image.
Embodiment
Next enumerate embodiment, the present invention is described more specifically.
In embodiment and comparative example, as if not specifying, the % of expression content or usage quantity and part all are benchmark with the quality.
In following examples, the structure of compound is by NMR (JMM-ECA-500; NEC (strain) system) confirms.
(embodiment 1)
After in 18.2 parts of 5-nitro anthranilic acids (Tokyo changes into industry (strain) system), adding 80 parts of water, add 0.4 part of sodium hydroxide again, make it dissolving.Add 19.7 part 35% sodium nitrite in aqueous solution down ice-cooled, the hydrochloric acid that then little by little adds 26.2 part 35% makes it dissolving, stirs 2 hours, obtains containing the suspension liquid of diazonium salt.
Then, make the compound shown in 14.9 parts of formulas (c-1) outstanding turbid in 100 parts of water, use sodium hydroxide that pH is adjusted into 9.0.At this moment, last 15 minutes use pumps and drip the above-mentioned suspension that contains diazonium salt.After dripping end, restir 30 minutes obtains yellow suspension liquid.Stirred 1 hour.At 60 ℃ of yellow solids that following dry filter obtains of decompression, obtain 31.9 parts of compounds shown in the formula (I-1).
Figure BSA00000407748900121
The evaluation of compound (I-1)
1H-NMR：0.90(3H，t)，1.28(2H，m)，1.50(2H，m)，2.51(3H，s)，3.82(2H，t)，8，18(1H，d)，8.47(1H，m)，8.73(1H，d)
(embodiment 2)
In embodiment 1, the compound shown in the use formula (c-2) substitutes above-mentioned formula (c-1), carries out the compound experiment identical with embodiment 1, obtains compound (I-11).
Figure BSA00000407748900122
The evaluation of compound (I-11)
1H-NMR：1.44(3H，d)，2.22(3H，s)，3.87(2H，t)，7.63(2H，d)，8.05(1H，d)，8.39(1H，m)，8.68(1H，d)
(comparative example 1)
In embodiment 1, use the amino terephthaldehyde's acid substitution of 2-5-nitro anthranilic acid, the compound shown in the formula (c-3) replaces the compound shown in the aforementioned formula (c-1), carries out the compound experiment identical with embodiment 1, obtains compound (d-2).
Figure BSA00000407748900123
The mensuration of＜molar absorptivity 〉
In dimethyl formamide, constant volume is 250cm with the compound dissolution of 0.35g embodiment 1,2 and comparative example 1 gained 3, get 2cm wherein 3Solution dilutes with dimethyl formamide, and making volume is 100cm 3, make the solution that concentration is 0.028g/L.This solution is measured maximum absorption wavelength (λ max) and molar absorptivity with ultraviolet-visible pectrophotometer (V-650DS, Japanese beam split (strain) system) (quartz container, optical length 1cm).
The results are shown in Table 2.
[table 2]
Compound ?λmax(nm) Molar absorptivity
Embodiment 1 I-1 ?435 54000
Embodiment 2 I-11 ?454 58000
Comparative example 1 d-2 ?440 42000
Embodiment 3
(modulation of colored photosensitive polymer combination)
(A) tinting material: compound (I-1): the synthetic compound is 20 parts among the embodiment 1
(B-1) resin: 70 parts of methacrylic acids/methacrylic acid benzyl ester multipolymer (mol ratio: 30/70, weight-average molecular weight 10700, acid number 70mgKOH/g)
(C-1) polymerizable compound: 30 parts of dipentaerythritol acrylates (Japanese chemical drug society system)
(D-1) Photoepolymerizationinitiater initiater: 15 parts of benzyl dimethyl ketal (イ Le ガ キ ユ ア 651, チ バ ジ ヤ パ Application society system)
(E-1) solvent: N, 680 parts of N '-dimethyl formamide
Mix mentioned component and obtain colored resin composition.
(making of colour filter)
It is on glass to adopt spin-coating method that the colored resin composition of above-mentioned acquisition is coated, and makes the volatile component volatilization.After the cooling, use silica glass system photomask and exposure machine to carry out rayed with pattern.After the rayed, develop in potassium hydroxide aqueous solution, heating obtains colour filter under 200 ℃ in baking oven.
Embodiment 4
Except synthetic compound (I-1) among the embodiment 1 being replaced with among the embodiment 2 the synthetic compound (I-11), carry out the experiment identical with embodiment 3, obtain colored resin composition and colour filter.
Compound of the present invention as can be known from the results of Table 2, its molar absorptivity height demonstrates high branch optical concentration.In addition, the colored resin composition that contains this compound has excellent look performance, can be used to make high-quality colour filter.
Utilizability on the industry
Compound of the present invention can be applied to dyestuff. Compound of the present invention because the molar absorption coefficient height, divides the optical concentration height, so can be used for using as dyestuff such as the colour filter of the display unit such as, liquid crystal indicator.

Claims (5)

1. the compound shown in the formula (I),
Figure FSA00000407748800011
In the formula (I), R 1Alkyl, the aryl of carbonatoms 6～21 or the aralkyl of carbonatoms 7～21 of expression carbonatoms 1～8;
R 2Expression hydrogen atom, cyano group or formamyl;
R 3The alkyl or the trifluoromethyl of expression carbonatoms 1～4;
R 4～R 7Represent the alkyl of hydrogen atom, carbonatoms 1～8, the alkoxyl group of carbonatoms 1～8, alkoxyalkyl, hydroxyl, cyano group or the nitro of carbonatoms 2～8 independently of each other, R 4～R 7In have at least one the expression nitro.
2. compound according to claim 1, R 5Perhaps R 6Be nitro.
3. according to claim 1 or 2 described compounds, R 2Be cyano group.
4. a dyestuff is an effective constituent with the described compound of claim 1.
5. a colored resin composition contains the described dyestuff of claim 4, resin and solvent.
CN2010106206391A 2009-12-25 2010-12-22 Pyridone compound Pending CN102108061A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104031652A (en) * 2014-06-25 2014-09-10 北京大学 Iodine bond liquid crystal with reversible photoinduced phase transition behavior and preparation method thereof

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4368260A (en) * 1980-12-27 1983-01-11 Konishiroku Photo Industry Co., Ltd. Photographic light sensitive element
US4486237A (en) * 1982-02-22 1984-12-04 Montefluous S.P.A. Composite pigments and process for their preparation
JPS6027594A (en) * 1983-07-27 1985-02-12 Mitsubishi Chem Ind Ltd Pyridone azo dye for thermal transfer recording
JPH05331382A (en) * 1992-06-03 1993-12-14 Mitsubishi Kasei Corp Pyridone azo pigment and thermal transfer sheet prepared using the same
EP0442466B1 (en) * 1990-02-14 1995-01-18 Mitsubishi Chemical Corporation Thermal transfer recording sheet and ink composition for producing the same
JP3163778B2 (en) * 1992-09-21 2001-05-08 三菱化学株式会社 Pyridone azo dye and thermal transfer sheet
CN1322227A (en) * 1999-07-29 2001-11-14 三井化学株式会社 Yellow compound and water-based ink-jet recording ink containing compound
JP2004300224A (en) * 2003-03-31 2004-10-28 Mitsui Chemicals Inc Water-based ink
CN1276035C (en) * 2001-09-28 2006-09-20 三井化学株式会社 Water-color ink
CN100506816C (en) * 2005-12-30 2009-07-01 明德国际仓储贸易(上海)有限公司 Yellow dye compound and its ink composition

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3578752B2 (en) * 2001-09-28 2004-10-20 三井化学株式会社 Water-based ink
JP5013746B2 (en) * 2006-05-19 2012-08-29 キヤノン株式会社 Dye compound and recording ink
JP5634019B2 (en) * 2008-10-14 2014-12-03 キヤノン株式会社 Dye compound and ink containing the dye compound

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4368260A (en) * 1980-12-27 1983-01-11 Konishiroku Photo Industry Co., Ltd. Photographic light sensitive element
US4486237A (en) * 1982-02-22 1984-12-04 Montefluous S.P.A. Composite pigments and process for their preparation
JPS6027594A (en) * 1983-07-27 1985-02-12 Mitsubishi Chem Ind Ltd Pyridone azo dye for thermal transfer recording
EP0442466B1 (en) * 1990-02-14 1995-01-18 Mitsubishi Chemical Corporation Thermal transfer recording sheet and ink composition for producing the same
JPH05331382A (en) * 1992-06-03 1993-12-14 Mitsubishi Kasei Corp Pyridone azo pigment and thermal transfer sheet prepared using the same
JP3163778B2 (en) * 1992-09-21 2001-05-08 三菱化学株式会社 Pyridone azo dye and thermal transfer sheet
CN1322227A (en) * 1999-07-29 2001-11-14 三井化学株式会社 Yellow compound and water-based ink-jet recording ink containing compound
CN1276035C (en) * 2001-09-28 2006-09-20 三井化学株式会社 Water-color ink
JP2004300224A (en) * 2003-03-31 2004-10-28 Mitsui Chemicals Inc Water-based ink
CN100506816C (en) * 2005-12-30 2009-07-01 明德国际仓储贸易(上海)有限公司 Yellow dye compound and its ink composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
李慕洁等: "吡啶酮系偶氮染料光谱特性的研究", 《大连工学院学报》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104031652A (en) * 2014-06-25 2014-09-10 北京大学 Iodine bond liquid crystal with reversible photoinduced phase transition behavior and preparation method thereof

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