CN102134262A - Pyridine ketone complex - Google Patents

Pyridine ketone complex Download PDF

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CN102134262A
CN102134262A CN2010106209493A CN201010620949A CN102134262A CN 102134262 A CN102134262 A CN 102134262A CN 2010106209493 A CN2010106209493 A CN 2010106209493A CN 201010620949 A CN201010620949 A CN 201010620949A CN 102134262 A CN102134262 A CN 102134262A
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carbonatoms
methyl
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hydrogen atom
compound
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辰巳泰基
朴昭妍
植田裕治
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Sumitomo Corp
Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
    • 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
    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • 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
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
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    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form

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  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Pyridine ketone complex, dye with the pyridine ketone as the active ingredient, dye, resin and coloring resin composition of a solvent having pyridine ketone complex as the active ingredient.

Description

The pyridone complex compound
Technical field
The present invention relates to be used for the compound of dyestuff.
Background technology
Always, metallic complex salt compound pigment is used in various fields (for example, filamentary material, liquid crystal indicator etc.), utilizes reflected light or transmitted light to develop the color.Such pigment is known to be had for example is the chromium complex dyes of ligand with the azo-compound, the C.I. solvent yellow 21 shown in the following formula (a).
[non-patent literature 1] Industrial Dyes Chemistry, Properties, Applications, WILEY-VCH, 2003.
Summary of the invention
Existing known above-claimed cpd, its molar absorptivity is little, divides optical concentration very not satisfactory.
The invention provides following [1]～[7].
[1] compound shown in a kind of formula (0).
Figure BSA00000408378500012
[in the formula (0), R 11 valency saturated hydrocarbyl of expression carbonatoms 1～8, the hydrogen atom that this saturated hydrocarbyl comprised can be by-OR 8,-COOR 8,-OCOR 8,-CONR 8R 9, 1 valency aromatic hydrocarbyl of carbonatoms 6～10 or halogen atom replace, this saturated hydrocarbyl is contained-CH 2-among not with-O-bonding-CH 2-can be replaced by-CO-;
R 2The expression hydrogen atom ,-CN or-CONH 2Base;
R 3The alkyl of the carbonatoms 1～4 that expression can be replaced by halogen atom;
R 4a～R 7aExpression-R independently of each other 8,-OR 8,-COOR 8,-COR 8,-OCOOR 8,-OCOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K ,-SO 2NR 8R 9Perhaps-NR 11R 12, R 4aAnd R 5a, R 5aAnd R 6aAnd R 6aAnd R 7aBonding forms 6～7 yuan of rings that contain phenyl ring carbon mutually;
R 8And R 9Expression hydrogen atom, 1 valency aliphatic alkyl of carbonatoms 1～8, the aralkyl of carbonatoms 7～12 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10, the hydrogen atom that this aliphatic alkyl, this aralkyl and this aromatic hydrocarbyl comprised can be by-OR 10Replace;
R 10Expression hydrogen atom, 1 valency saturated hydrocarbyl of carbonatoms 1～8 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10;
R 11And R 12Represent 1 valency aliphatic alkyl of hydrogen atom, carbonatoms 1～8, the acyl group or the tetrahydrofurfuryl of carbonatoms 2～8 independently of each other, R 11And R 12Bonding forms the ring that contains nitrogen-atoms mutually;
A +The tetra-allkylammonium positive ion of expression hydrogen positive ion (ヒ De ロ Application), sodium positive ion, potassium positive ion or carbonatoms 1～4.]
[2] compound shown in a kind of formula (I).
Figure BSA00000408378500021
[in the formula (I), R 11 valency saturated hydrocarbyl of expression carbonatoms 1～8, the hydrogen atom that this saturated hydrocarbyl comprised can be by-OR 8,-COOR 8,-OCOR 8,-CONR 8R 9, 1 valency aromatic hydrocarbyl of carbonatoms 6～10 or halogen atom replace, this saturated hydrocarbyl is contained-CH 2-among not with-O-bonding-CH 2-can be replaced by-CO-;
R 2The expression hydrogen atom ,-CN or-CONH 2
R 3The alkyl of expression hydrogen atom, the carbonatoms 1～4 that can be replaced by halogen atom;
R 4～R 7Expression-R independently of each other 8,-OR 8,-COOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K or-SO 2NR 8R 9
R 8And R 9Expression hydrogen atom, 1 valency aliphatic alkyl of carbonatoms 1～8, the aralkyl of carbonatoms 7～12 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10, the hydrogen atom that this aliphatic alkyl, this aralkyl and this aromatic hydrocarbyl comprised can be by-OR 10Replace;
R 10Expression hydrogen atom, 1 valency saturated hydrocarbyl of carbonatoms 1～8 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10;
A +The tetra-allkylammonium positive ion of expression hydrogen positive ion, sodium positive ion, potassium positive ion or carbonatoms 1～4.]
[3] above-mentioned [1] or [2] described compound, R 1For can by-OH-or-OCOR 81 valency saturated hydrocarbyl of the carbonatoms 1～8 that replaces.
[4] the described compound in above-mentioned [1]～[3], R 4～R 7In have 3 at least for hydrogen atom.
[5] the described compound in above-mentioned [1]～[4], R 2For-CN.
[6] more than one dyestuffs that to state each described compound of [1]～[5] be effective constituent.
[7] a kind of containing [6] described dyestuff, resin and the colored resin composition of solvent.
Compound of the present invention, its molar absorptivity is big, divides the optical concentration height.
Embodiment
Compound of the present invention is the represented compound of formula (0) (below, also claim compound (0)).Compound of the present invention also can comprise its tautomer.
Figure BSA00000408378500031
[in the formula (0), R 11 valency saturated hydrocarbyl of expression carbonatoms 1～8, the hydrogen atom that this saturated hydrocarbyl comprised can be by-OR 8,-COOR 8,-OCOR 8,-CONR 8R 9, 1 valency aromatic hydrocarbyl of carbonatoms 6～10 or halogen atom replace, this saturated hydrocarbyl is contained-CH 2-among not with-O-bonding-CH 2-can be replaced by-CO-;
R 2The expression hydrogen atom ,-CN or-CONH 2Base;
R 3The alkyl of the carbonatoms 1～4 that expression can be replaced by halogen atom;
R 4a～R 7aExpression-R independently of each other 8,-OR 8,-COOR 8,-COR 8,-OCOOR 8,-OCOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K ,-SO 2NR 8R 9Perhaps-NR 11R 12, R 4aAnd R 5a, R 5aAnd R 6aAnd R 6aAnd R 7aBonding forms 6～7 yuan of rings that contain phenyl ring carbon mutually;
R 8And R 9Expression hydrogen atom, 1 valency aliphatic alkyl of carbonatoms 1～8, the aralkyl of carbonatoms 7～12 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10, the hydrogen atom that this aliphatic alkyl, this aralkyl and this aromatic hydrocarbyl comprised can be by-OR 10Replace;
R 10Expression hydrogen atom, 1 valency saturated hydrocarbyl of carbonatoms 1～8 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10;
R 11And R 12Represent 1 valency aliphatic alkyl of hydrogen atom, carbonatoms 1～8, the acyl group or the tetrahydrofurfuryl of carbonatoms 2～8 independently of each other, R 11And R 12Bonding forms the ring that contains nitrogen-atoms mutually;
A +The tetra-allkylammonium positive ion of expression hydrogen positive ion, sodium positive ion, potassium positive ion or carbonatoms 1～4.]
Compound shown in the compound preferred formula of the present invention (I) (below, also claim compound (I)).
Figure BSA00000408378500041
[in the formula (I), R 11 valency saturated hydrocarbyl of expression carbonatoms 1～8, the hydrogen atom that this saturated hydrocarbyl comprised can be by-OR 8,-COOR 8,-OCOR 8,-CONR 8R 9, 1 valency aromatic hydrocarbyl of carbonatoms 6～10 or halogen atom replace, this saturated hydrocarbyl is contained-CH 2-among not with-O-bonding-CH 2-can be replaced by-CO-;
R 2The expression hydrogen atom ,-CN or-CONH 2
R 3The alkyl of expression hydrogen atom, the carbonatoms 1～4 that can be replaced by halogen atom;
R 4～R 7Expression-R independently of each other 8,-OR 8,-COOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K or-SO 2NR 8R 9
R 8And R 9Expression hydrogen atom, 1 valency aliphatic alkyl of carbonatoms 1～8, the aralkyl of carbonatoms 7～12 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10, the hydrogen atom that this aliphatic alkyl, this aralkyl and this aromatic hydrocarbyl comprised can be by-OR 10Replace;
R 10Expression hydrogen atom, 1 valency saturated hydrocarbyl of carbonatoms 1～8 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10;
A +The tetra-allkylammonium positive ion of expression hydrogen positive ion, sodium positive ion, potassium positive ion or carbonatoms 1～4.]
R 11 valency saturated hydrocarbyl for carbonatoms 1～8,1 valency saturated hydrocarbyl of preferred carbonatoms 1～6, more preferably 1 valency saturated hydrocarbyl of carbonatoms 1～4,1 valency saturated hydrocarbyl of further preferred carbonatoms 2～4, preferred especially carbonatoms 2 or 41 valency saturated hydrocarbyl.
In addition, when the hydrogen atom that this saturated hydrocarbyl comprised is substituted, preferably by-OR 8,-OCOR 8Perhaps 1 valency aromatic hydrocarbyl of carbonatoms 6～10 replaces; As quilt-OR 8During replacement, R 8Be preferably hydrogen atom, as quilt-OCOR 8During replacement, R 8Be preferably 1 valency aliphatic alkyl or phenyl of carbonatoms 6～8.
R 1And R 10In 1 valency saturated hydrocarbyl of carbonatoms 1～8 can enumerate straight chain saturation alkane bases such as methyl, ethyl, n-propyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl for example;
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 saturated hydrocarbon groups such as 2-diethyl butyl;
Ring type saturated hydrocarbyls such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl, ring octyl group.
R 8And R 9In 1 valency aliphatic alkyl of carbonatoms 1～8, except the above-mentioned straight chain saturation alkane base of enumerating and branched saturated hydrocarbon group, can also enumerate vinyl, propenyl, pseudoallyl, butenyl, 2-methylpropenyl etc.
R 8And R 9In the aralkyl of carbonatoms 7～12 can enumerate phenmethyl, styroyl, hydrocinnamyl, menaphthyl, naphthalene ethyl etc.
R 8, R 9And R 10In 1 valency aromatic hydrocarbyl of carbonatoms 6～10 can enumerate phenyl, toluyl, xylyl, naphthyl etc.
-CH 2The saturated hydrocarbyl that-quilt-CO-replaces can be enumerated, and for example acetonyl, 3-oxo butyl, 2-oxo butyl, 3-oxo amyl group, 2-oxo amyl group, 3-oxo-hexyl etc. contain the saturated hydrocarbyl of oxo base;
Aromatic hydrocarbyls such as phenacyl, 2-oxo-2-naphthyl ethyl, 2-oxo-2-hydroxyphenyl ethyl, 2-oxo-2 hydroxy naphthalene base ethyl, 2-oxo-2-p-methoxy-phenyl ethyl, 2-oxo-2-methoxyl group naphthyl ethyl, 2-oxo-3-phenyl propyl, 2-oxo-3-naphthyl propyl group and contain saturated hydrocarbyl of oxo base etc.
Hydrogen atom can be enumerated by the saturated hydrocarbyl that halogen atom replaces, for example methyl fluoride, trifluoromethyl, fluoro ethyl, fluoropropyl, fluorine butyl, chloromethyl, chloroethyl, chloropropyl, chlorobutyl, brooethyl, bromotrifluoromethane, bromopropyl, brombutyl, iodomethyl, iodine ethyl, iodine propyl group, iodine butyl etc.
-OR 8Can enumerate, for example hydroxyl, methoxyl group, oxyethyl group, propoxy-, butoxy, pentyloxy, hexyloxy, heptan oxygen base, octyloxy, 2-ethyl hexyl oxy, phenoxy group, benzyloxy, benzoyloxy etc.
Quilt-OR 10Replace-OR 8Can enumerate, for example methoxymethyl, methoxy ethyl, methoxy-propyl, methoxyl group butyl, methoxyl group 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.
Hydrogen atom quilt-OR 8The saturated hydrocarbyl that replaces can be enumerated, and for example methylol, hydroxyethyl, hydroxypropyl, hydroxyl butyl, hydroxyl methoxymethyl, 2-'-hydroxyethoxy ylmethyl, 2-hydroxyl methoxy ethyl, 2-(2-hydroxyl-oxethyl) ethyl, 2-oxo-4-hydroxyl butyl etc. contain the saturated hydrocarbyl of hydroxyl;
Methoxymethyl, ethoxyl methyl, propoxy-methyl, methoxy ethyl, ethoxyethyl group, propoxy-ethyl, methoxy-propyl, ethoxycarbonyl propyl, propoxy-propyl group, 2-oxo-4-methoxyl group butyl etc. contain the saturated hydrocarbyl of alkoxyl group;
Methoxyl group methoxy methyl, 2-methoxyl group ethoxymethyl, oxyethyl group methoxy methyl, 2-oxyethyl group ethoxymethyl, propoxy-methoxyl methyl, 2-propoxy-ethoxymethyl, 2-methoxyl group methoxy ethyl, 2-(2-methoxy ethoxy) ethyl, 2-oxyethyl group methoxy ethyl, 2-(2-ethoxy ethoxy) ethyl, 2-propoxy-methoxyethyl, 2-(2-propoxy-oxyethyl group) ethyl etc. contain the saturated hydrocarbyl of alkoxyalkyl;
Phenoxymethyl, 1-naphthyloxy methyl, 2-naphthyloxy methyl, oxybenzene oxygen ylmethyl, hydroxyl naphthyloxy methyl, methoxyl group phenoxymethyl, methoxynaphthalene oxygen ylmethyl, 3-phenoxy acetone base etc. contain the saturated hydrocarbyl of aryloxy;
Benzyloxymethyl, naphthyl methoxymethyl, hydroxyl benzyloxymethyl, hydroxyl naphthyl methoxymethyl, methoxyl group benzyloxy methyl, methoxy-naphthyl methoxyl methyl, phenoxy group ethoxymethyl, naphthyloxy ethoxymethyl etc. contain the saturated hydrocarbyl of aralkoxy etc.
-COOR 8Can enumerate, for example methoxycarbonyl, ethoxy carbonyl, benzyloxycarbonyl etc.
Hydrogen atom quilt-COOR 8The saturated hydrocarbyl that replaces can be enumerated, and for example carboxymethyl, propyloic, carboxylic propyl group, carboxylic butyl etc. contain the saturated hydrocarbyl of carboxyl;
Methoxycarbonylmethy-, methoxyl group carbonyl ethyl, oxyethyl group carbonyl methyl, oxyethyl group carbonyl ethyl, propoxy-carbonyl methyl, propoxy-carbonyl ethyl, butoxy carbonyl methyl, butoxy carbonyl ethyl, phenoxy group methoxycarbonylmethy-, 2-hydroxyl-oxethyl carbonyl methyl, 2-methoxy ethoxy carbonyl methyl etc. contain the saturated hydrocarbyl of alkoxy carbonyl;
Phenoxy group carbonyl methyl, naphthyloxy carbonyl methyl etc. contain the saturated hydrocarbyl of aryloxycarbonyl;
Benzyloxy carbonyl methyl, naphthyl methoxycarbonylmethy-etc. contain the saturated hydrocarbyl of aromatic alkoxy carbonyl;
2-oxopropoxy carbonyl methyl, 2-(2-oxopropoxy carbonyl) ethyl, 3-(2-oxopropoxy carbonyl) propyl group, 2-oxo butoxy carbonyl methyl, 2-(2-oxo butoxy carbonyl) ethyl, 3-(2-oxo butoxy carbonyl) propyl group, 2-oxo pentyloxy carbonyl methyl, 2-(2-oxo pentyloxy carbonyl) ethyl, 3-(2-oxo pentyloxy carbonyl) propyl group, 3-oxo butoxy carbonyl methyl, 2-(3-oxo butoxy carbonyl) ethyl, 3-(3-oxo butoxy carbonyl) propyl group, 3-oxo pentyloxy carbonyl methyl, 2-(3-oxo pentyloxy carbonyl) ethyl, 3-(3-oxo pentyloxy carbonyl) propyl group, 2-oxo hexyloxy carbonyl methyl, 2-(2-oxo hexyloxy carbonyl) ethyl, 3-(2-oxo hexyloxy carbonyl) propyl group etc. contains-CH 2The saturated hydrocarbyl of the alkoxy carbonyl that-quilt-CO-replaces;
3-methoxycarbonyl-2-oxopropyl, 4-methoxycarbonyl-3-oxo butyl, 5-methoxycarbonyl-4-oxo amyl group, 3-ethoxy carbonyl-2-oxopropyl, 4-ethoxy carbonyl-3-oxo butyl, 5-ethoxy carbonyl-4-oxo amyl group, 3-propoxycarbonyl-2-oxopropyl, 4-propoxycarbonyl-3-oxo butyl, 5-propoxycarbonyl-4-oxo amyl group, 4-methoxycarbonyl-2-oxo butyl, 4-methoxycarbonyl-3-oxo amyl group, 5-methoxycarbonyl-4-oxo-hexyl, 4-ethoxy carbonyl-2-oxo butyl, 4-ethoxy carbonyl-3-oxo amyl group, 5-ethoxy carbonyl-4-oxo-hexyl, 4-propoxycarbonyl-2-oxo butyl, 4-propoxycarbonyl-3-oxo amyl group, 5-propoxycarbonyl-4-oxo-hexyl etc. contain alkoxy carbonyl and-CH 2-by-saturated hydrocarbyl that CO-replaced etc.
Hydrogen atom quilt-CONR 8R 9The saturated hydrocarbyl that replaces can be enumerated, for example N-methyl aminocarbonyl methyl, N-methyl aminocarbonyl ethyl, N, N-carbonyl dimethyl ammonium methyl, N, N-carbonyl dimethyl ammonium ethyl, N, N-ethyl-methyl aminocarbonyl methyl, N, N-ethyl-methyl carbonyl ethyl etc. contains the saturated hydrocarbyl of alkyl-substituted amino formyl radical;
N-phenylamino carbonyl methyl, N, N-phenyl methyl carbonyl methyl, N, N-biphenyl carbonyl methyl, N, N-phenylbenzyl carbonyl methyl etc. contains the saturated hydrocarbyl of aryl substituted-amino formyl radical;
N-phenmethyl aminocarbonyl methyl, N, N-diphenyl-methyl carbonyl methyl, N, N-two (2-styroyl) carbonyl methyl etc. contains the saturated hydrocarbyl of aralkyl substituted-amino formyl radical;
-OCOR 8Can enumerate, for example acetoxyl group, trimethyl acetoxyl, benzoyloxy etc.
Hydrogen atom quilt-OCOR 8The saturated hydrocarbyl that replaces can be enumerated, and for example acetoxy-methyl, acetoxyl group ethyl, ethyl phosphinylidyne oxygen ylmethyl, ethyl carbon acyloxy ethyl, propyl group phosphinylidyne oxygen ylmethyl, propyl group carbon acyloxy ethyl, butyl phosphinylidyne oxygen ylmethyl, butyl carbon acyloxy ethyl, hexylyloxy ethyl, 2-ethyl butyryl acyloxy ethyl, 2-ethyl hexanoyl oxygen base ethyl, 2-propyl group hexylyloxy ethyl, trimethyl acetoxyl ethyl, 2-methyl-prop acyl-oxygen ethyl etc. contain the saturated hydrocarbyl of alkyl carbon acyloxy;
Benzoyloxy methyl, benzoyloxy ethyl, naphthyl oxygen carbonyl methyl, phenmethyl phosphinylidyne oxygen ylmethyl, naphthyl methyl phosphinylidyne oxygen ylmethyl, tolyl acid ylmethyl, 2-tolyl acid base ethyl, 4-tolyl acid base ethyl, 3,4-mesitylenic acid base ethyl, hydroxy-benzoic acid ylmethyl, methoxybenzoic acid ylmethyl, 4-methoxybenzoic acid base ethyl, 3,4-dimethoxybenzoic acid base ethyl etc. contains the saturated hydrocarbyl of aromatic hydrocarbyl and carbon acyloxy etc.
-COR 8Can give an example, for example ethanoyl, propionyl, isobutyryl, pentanoyl and isovaleryl etc.
-OCOOR 8Can enumerate, for example methoxyl group carbon acyloxy, oxyethyl group carbon acyloxy, positive propoxy carbon acyloxy, isopropoxy carbon acyloxy, n-butoxy carbon acyloxy, isobutoxy carbon acyloxy, tert butoxy carbonyl oxygen base, n-pentyloxy carbon acyloxy, phenoxy group carbon acyloxy etc.
Hydrogen atom can be enumerated by the saturated hydrocarbyl that the aromatic hydrocarbyl of carbonatoms 6～10 replaces, for example group shown in phenmethyl, 1-menaphthyl, 2-menaphthyl, the following formula etc.
Figure BSA00000408378500091
R 1Preferred hydrogen atom quilt-COOR 8The saturated hydrocarbyl and the hydrogen atom quilt-OCOR that replace 8The saturated hydrocarbyl that replaces, the more preferably group shown in formula (f-1)～formula (f-14).Work as R 1During for above-mentioned group, compound of the present invention demonstrates the tendency of high resolution in organic solvent.In formula (f-1)～formula (f-14), * represent with the pyridone ring on the position of nitrogen atom bonding.
Figure BSA00000408378500092
R 2For hydrogen atom ,-CN or-CONH 2Wherein ,-CN is easier to start with owing to raw material, so preferred.
R 3Alkyl for hydrogen atom, the carbonatoms 1～4 that can be replaced by halogen atom.
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.
The alkyl of the carbonatoms 1～4 that is replaced by halogen atom can be enumerated, for example trifluoromethyl, pentafluoroethyl group etc.
R 3Preferable methyl, trifluoromethyl, special preferable methyl.
R 4a～R 7aBe preferably independently of each other-R 8,-OR 8,-COOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K ,-SO 2NR 8R 9Perhaps-NR 11R 12
R 4～R 7Expression-R independently of each other 8,-OR 8,-COOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K or-SO 2NR 8R 9
R 4a～R 7aIn-NR 11R 12Can enumerate for example N-methylamino, N, N-dimethylamino, N-ethylamino, N, N-diethylamino, N-propyl group amino, N, N-dipropyl amino, N-butyl amino, N, N-dibutylamino, N-amyl group amino, N-acetylamino etc.
R 11And R 12Bonding formation comprises the ring of nitrogen-atoms-NR mutually 11R 12Can enumerate, for example 1-pyrazolyl, pyrrolidyl, piperidino, morpholinyl etc.
Wherein, from this point of the solvability organic solvent, preferred N-acetylamino.
R 4a～R 7aAnd R 4～R 7In-SO 2NR 8R 9Can enumerate, not have the sulfamyl of replacement, N-1 replacement sulfamyl and N, N-2 replaces sulfamyl.
N-1 replaces sulfamyl can be enumerated, N-methyl sulfamyl for example, N-ethyl sulfamyl, N-propyl group sulfamyl, N-sec.-propyl sulfamyl, N-butyl sulfamyl, N-isobutyl-sulfamyl, N-sec-butyl sulfamyl, N-tertiary butyl sulfamyl, N-amyl group sulfamyl, N-(1-ethyl propyl) sulfamyl, N-(1, the 1-dimethyl propyl) sulfamyl, N-(1, the 2-dimethyl propyl) sulfamyl, N-(2, the 2-dimethyl propyl) sulfamyl, N-(1-methyl butyl) sulfamyl, N-(2-methyl butyl) sulfamyl, N-(3-methyl butyl) sulfamyl, N-cyclopentyl sulfamyl, N-hexyl sulfamyl, N-(1, the 3-dimethylbutyl) sulfamyl, N-(3, the 3-dimethylbutyl) sulfamyl, N-heptyl sulfamyl, N-(1-methyl hexyl) sulfamyl, N-(1,4-dimethyl amyl group) sulfamyl, N-octyl group sulfamyl, N-(2-ethylhexyl) sulfamyl, N-(1, the 5-dimethyl) hexyl sulfamyl, N-(1,1,2, the 2-tetramethyl butyl) sulfamyl, aliphatic alkyls such as N-allyl group sulfamyl replace N-1 and replace sulfamyl;
The N-1 that aliphatic alkyl replaced that N-(2-hydroxyethyl) sulfamyl, N-(3-hydroxypropyl) sulfamyl, N-(2-hydroxypropyl) sulfamyl, N-(2, the 3-dihydroxypropyl) sulfamyl, N-(2-hydroxyl butyl) sulfamyl, N-(4-hydroxyl butyl) sulfamyl, N-(1-hydroxymethyl ethyl) sulfamyl etc. have hydroxyl replaces sulfamyl;
N-(2-methoxy ethyl) sulfamyl, N-(2-ethoxyethyl group) sulfamyl, N-(1-methoxy-propyl) sulfamyl, N-methoxy-propyl sulfamyl, N-ethoxycarbonyl propyl sulfamyl, N-propoxy-propyl group sulfamyl, N-isopropoxide propyl sulfamyl, N-hexyloxy propyl group sulfamyl, N-(2-ethyl hexyl oxy propyl group) sulfamyl, N-(3-tert.-butoxy propyl group) sulfamyl, N-(4,4-dimethoxy butyl) sulfamyl, N-methoxyl group hexyl sulfamyl etc. has the alkyl of alkoxyl group or the N-1 of cycloalkyl substituted replaces sulfamyl;
N-[1-(2-ethoxy ethoxy) propyl group] sulfamyl etc. has the N-1 that the aliphatic alkyl of alkoxyalkyl replaces and replaces sulfamyl;
The N-1 that aryl such as N-phenyl sulfamoyl base, N-(1-naphthyl) sulfamyl replace replaces sulfamyl;
N-phenmethyl sulfamyl, N-(1-phenylethyl) sulfamyl, N-(2-phenylethyl) sulfamyl, N-(3-phenyl propyl) sulfamyl, N-(4-phenyl butyl) sulfamyl, N-[2-(2-naphthyl) ethyl] sulfamyl, N-[2-(4-aminomethyl phenyl) ethyl] N-1 that replaces of aralkyl such as sulfamyl, N-(3-phenyl-1-propyl group) sulfamyl, N-(3-phenyl-1-methyl-propyl) sulfamyl replaces sulfamyl etc.;
N-(3,4,5-trimethoxy phenmethyl) sulfamyl, N-[2-(3, the 4-Dimethoxyphenyl) ethyl] sulfamyl, N-[2-(2-ethoxyl phenenyl) ethyl] sulfamyl etc. has the N-1 that substituent aralkyl replaces and replaces sulfamyl;
N, N-2 replace sulfamyl can be enumerated, for example N, N-dimethylamino alkylsulfonyl, N, N-ethyl-methyl sulfamyl, N, N-diethyl amino alkylsulfonyl, N, N-propyl group methyl sulfamyl, N, N-isopropyl methyl sulfamyl, N, N-tertiary butyl methyl sulfamyl, N, N-butyl ethyl sulfamyl, N, N-two (1-methyl-propyl) sulfamyl, N, the N that N-heptyl methyl sulfamyl etc. are replaced by 2 aliphatic alkyls, N-replaces sulfamyl;
N, N-two (2-hydroxyethyl) sulfamyl, N, N-two (2-methoxy ethyl) sulfamyl, N, N-two (2-ethoxyethyl group) sulfamyl etc. has the N that substituent aliphatic alkyl replaces, and N-2 replaces sulfamyl etc.
-SO 2NR 8R 9Contained R 8And R 9The branched-chain alkyl of preferred carbonatoms 6～8, allyl group, phenyl, the aralkyl of carbonatoms 8～10, the alkyl or aryl that contains hydroxyl of carbonatoms 2～8, the perhaps alkyl or aryl that contains alkoxyl group of carbonatoms 2～8, preferred especially 2-ethylhexyl.
A +The tetra-allkylammonium positive ion of expression hydrogen positive ion, sodium positive ion, potassium positive ion or carbonatoms 1～4.
The tetra-allkylammonium positive ion is the quaternary ammonium positive ion with 4 alkyl, and the carbonatoms of 1 alkyl is 1～4.
This tetra-allkylammonium positive ion can be enumerated, for example tetramethyl-ammonium positive ion, tetraethyl ammonium positive ion, TBuA positive ion, dimethyl dibutyl ammonium positive ion etc., preferably TBuA positive ion.
Compound (0) can be enumerated, for example compound (I-1)～compound (I-177) etc.In the table 1, nBu represents normal-butyl.R in the table 1 1When the hurdle note has the structural formula sequence number, be the sequence number of above-mentioned or following illustration unit structure formula.In formula (f-15)～formula (f-18), * represent with the pyridone ring on the position of nitrogen atom bonding.
Figure BSA00000408378500121
[table 1]
Figure BSA00000408378500122
Figure BSA00000408378500131
Figure BSA00000408378500141
Figure BSA00000408378500151
Figure BSA00000408378500161
Wherein, owing to divide the optical concentration height, so preferred compound (I-1)～compound (I-5), compound (I-143) and compound (I-156).
As one of method of making The compounds of this invention, the manufacture method of enumerating compound (I) describes.The compound of non-compound (I) also can be made according to the method identical with following formula: compound (I) manufacture method in the compound (0).
Compound (I) can use compound shown in the formula (d) (following also claim " compound (d) ") and chromium cpd, forms complex compound and makes.
[in the formula (d), R 1～R 7With represented same meaning in the formula (I).]
As the manufacture method of compound (d), can make 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, compound (d) can be made by making the pyridinone compounds generation diazo coupling reaction shown in diazonium salt shown in the formula (b) and the formula (c).Diazonium salt shown in the formula (b) can for example pass through, and the amine shown in the formula (a) is obtained by nitrous acid, nitrite or nitrous acid ester diazotization.
[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.Preferably have chloride ion, bromide ion, CH 3COO -
By the pyridinone compounds shown in diazonium salt shown in the formula (b) and the formula (c) is reacted, can make compound (d) in aqueous solvent.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 (d) 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 aforementioned 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.Preferably the crystal water of leaching etc. is cleaned, then carried out drying.In addition, as required, can also use known method such as recrystallization further to purify.
Compound (I) can preferably react down at 70～150 ℃ and make in 3～10 hours by making compound (d) and chromium cpd in aqueous solvent (for example, N, dinethylformamide, N-Methyl pyrrolidone etc.).
Above-mentioned chromium cpd can be enumerated, and formic acid chromium, chromium acetate, chromium chloride, chromium fluoride, chromium ammonium suplhate etc. are preferably enumerated formic acid chromium, chromium ammonium suplhate etc.
The compound (d) of the usage quantity of chromium cpd with respect to 1 mole is preferably 0.5～1 mole.
In addition, carry out, can also add mineral alkali in order to promote this reaction.
Above-mentioned mineral alkali can be enumerated, sodium hydroxide, calcium hydroxide, yellow soda ash, lime carbonate, sodium-acetate, calcium acetate etc., preferred yellow soda ash, sodium-acetate 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 inorganic salt (for example salt etc.) and water.For aforementioned inorganic salt, preferably be modulated into inorganic salt solution in advance, again reaction mixture is added in this aqueous solution.Temperature when adding reaction mixture is preferably more than 10 ℃ below 50 ℃, and is more preferably more than 10 ℃ below 40 ℃, further preferred more than 10 ℃ below 25 ℃.In addition, add to reaction mixture in the inorganic salt solution after, be preferably in and synthermally stirred about 0.5～2 hour down.Carry out drying after preferably the crystal water of leaching etc. being cleaned.In addition, as required, can also use known method such as recrystallization further to carry out purifying.
In view of the above, the compound of acquisition can be used as the dyestuff use.Its minute the optical concentration height, utilize reflected light or see through light to show, so can be applied to use as dyestuff in the colour filter of display unit such as liquid crystal indicator or the filamentary material.
Dyestuff of the present invention is to be the dyestuff of effective constituent with compound of the present invention.
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 24,49, and 90,91,118,119,122,124,125,127,130,132,160,218;
C.I. acid 73,91,92,97,138,151,211,274,289;
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 that the composition that removes in the colored resin composition after desolvating amounts to.
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 pigment can be distinguished individually or make up more than 2 kinds, with dyestuff of the present invention and usefulness.
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 % usually 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, triaizine compounds, 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 triaizine compounds 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 for example can use 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 above-mentioned 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 above-mentioned 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 the 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.In addition, 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) is made), mass analysis (LC:Agilent system 1200 types; MASS:Agilent system LC/MSD type) confirms.
(embodiment 1)
After in 13.0 parts of anthranilic acids (Tokyo changes into industry (strain) system), adding 90 parts of water, add 4.1 parts of sodium hydroxide again, make it dissolving.Add 19.5 parts of Sodium Nitrites down ice-cooled, then little by little add 58.53 part 35% hydrochloric acid.Afterwards, stirred 2 hours down,, add 200 part 9% thionamic acid aqueous solution stir about 5 minutes at leisure, obtain containing the suspension liquid of diazonium salt for the excessive nitrous acid of cooling fast ice-cooled.
Then, make the compound shown in 21.4 parts of formulas (c-1) outstanding turbid in 150 parts of water, use sodium hydroxide that pH is adjusted into 9.0.At this moment, keep the above-mentioned pH value that contains the diazonium salt suspension liquid in 8.0～9.5 scopes, it is lasted 30 minutes use pumps drip.After dripping end, under room temperature, stirred 2 hours, obtain the xanchromatic suspension liquid.At 60 ℃ of yellow solids that following dry filter obtains of decompression, obtain the compound shown in 30.5 parts of formulas (d-1).By 1H-NMR confirms its structure.
The evaluation of the compound shown in the formula (d-1)
1H-NMR (500MHz, δ value (ppM, TMS benchmark), DMSO-d 6): 0.90 (3H, t), 1.29 (2H, Sextet), 1.48 (2H, quintet), 2.58 (3H, s), 3.84 (2H, t), 7.31 (1H, t), 7.57 (1H, td), 7.84 (1H, d), 8.05 (1H, dd), 16.4 (1H, s).
Figure BSA00000408378500241
In the compound shown in 4.5 parts of formulas (d-1), add 225 parts of N-Methyl pyrrolidone be heated to 80 ℃ make it dissolving after, add 1.8 parts of formic acid chromium n hydrates (Na カ ラ イ テ ス Network (strain) system), in 130 ℃ of following stir abouts 7 hours, obtain dark orange solution.This solution is injected 500 parts of 1N aqueous hydrochloric acids, filter the orange solids of gained, after 50 parts of water cleanings 2 times,, obtain the compound (productive rate 78%) shown in 3.9 parts of formulas (I-1) 60 ℃ of following vacuum-dryings.
The evaluation of the compound shown in the formula (I-1)
(mass analysis) ionization pattern=ESI-:m/z=756.2[M-H] -
Accurate mass (Exact Mass): 757.2
Figure BSA00000408378500242
(embodiment 2)
After in 17.0 parts of anthranilic acids, adding 170 parts of water, add 5.4 parts of sodium hydroxide again, make it dissolving.Add 25.5 parts of Sodium Nitrites down ice-cooled, then little by little add 79.5 part 35% hydrochloric acid.Afterwards, stirred 2 hours down,, add 250 part 9% thionamic acid aqueous solution stir about 10 minutes at leisure, obtain containing the suspension liquid of diazonium salt for the excessive nitrous acid of cooling fast ice-cooled.
Then, make the compound shown in 24.1 parts of formulas (c-2) outstanding turbid in 170 parts of water, use sodium hydroxide that pH is adjusted into 9.0.At this moment, keep the above-mentioned pH value that contains the diazonium salt suspension liquid in 8.0～9.5 scopes, it is lasted 30 minutes use pumps drip.After dripping end, under room temperature, stirred 2 hours, obtain the xanchromatic suspension liquid.At 60 ℃ of yellow solids that following dry filter obtains of decompression, obtain the compound shown in 39.9 parts of formulas (d-2).By 1H-NMR confirms its structure.
The evaluation of the compound shown in the formula (d-2)
1H-NMR (500MHz, δ value (ppM, TMS benchmark), DMSO-d 6): 1.08 (3H, t), 2.58 (3H, s), 3.88 (2H, q), 7.32 (1H, t), 7.58 (1H, td), 7.85 (1H, d), 8.05 (1H, dd), 16.4 (1H, s).
Figure BSA00000408378500251
In the compound shown in 10 parts of formulas (d-2), add 200 parts of N-Methyl pyrrolidone be heated to 80 ℃ make it dissolving after, add 3.7 parts of formic acid chromium n hydrates, in 135 ℃ of following stir abouts 2 hours, then reduce the temperature to 80 ℃, add again after 1.2 parts of yellow soda ash, in 135 ℃ of following stir abouts 2 hours, obtain dark orange solution again.This solution is injected 1000 parts of 1N aqueous hydrochloric acids, filters the orange solids of gained, uses 80 parts of water cleanings 2 times after, 60 ℃ of following vacuum-dryings, obtain the compound (productive rate 68%) shown in 7.5 parts of formulas (I-2).
The evaluation of the compound shown in the formula (I-2)
(mass analysis) ionization pattern=ESI-:m/z=700.1[M-Na] -
Accurate mass (Exact Mass): 723.1
Figure BSA00000408378500261
(embodiment 3)
At 13.0 parts of 2-amino-1, behind 150 parts of water of adding, add 5.1 parts of sodium hydroxide again in the 4-benzene dicarboxylic acid, make it dissolving.Add 14.8 parts of Sodium Nitrites down ice-cooled, then little by little add 59.4 part 35% hydrochloric acid.Afterwards, stirred 3 hours down,, add 150 part 9% thionamic acid aqueous solution stir about 10 minutes at leisure, obtain containing the suspension liquid of diazonium salt for the excessive nitrous acid of cooling fast ice-cooled.
Then, make the compound shown in 16.2 parts of formulas (c-1) outstanding turbid in 120 parts of water, use sodium hydroxide that pH is adjusted into 9.0.At this moment, keep the above-mentioned pH value that contains the diazonium salt suspension liquid in 8.5～10.5 scopes, it is lasted 1 hour use pump drip.After dripping end, under room temperature, stirred 2 hours, obtain dark orange suspension liquid.It is 3 o'clock that adding 1N hydrochloric acid water dissolution makes the pH value, obtains yellow suspension liquid.At 60 ℃ of yellow solids that following dry filter obtains of decompression, obtain the compound shown in 24.9 parts of formulas (d-3).By 1H-NMR confirms its structure.
The evaluation of the compound shown in the formula (d-3)
1H-NMR (500MHz, δ value (ppM, TMS benchmark), DMSO-d6): 0.91 (3H, t), 1.31 (2H, sextet), 1.50 (2H, quintet), 2.47 (3H, s), 3.78 (2H, t), 7.74 (1H, d), 8.02 (1H, d), 8.30 (1H, s), 15.5 (1H, s).
Figure BSA00000408378500262
In the compound shown in 2.5 parts of formulas (d-3), add 125 parts of water be heated to 75 ℃ make it dissolving after, add 1.2 parts of formic acid chromium n hydrates, in 100 ℃ of following stir abouts 8 hours, obtain dark orange solution.This solution is injected 300 parts of 1N aqueous hydrochloric acids, after the orange solids of filtration gained,, obtain the compound (productive rate 65%) shown in 1.7 parts of formulas (I-3) 60 ℃ of following vacuum-dryings.
The evaluation of the compound shown in the formula (I-3)
(mass analysis) ionization pattern=ESI-:m/z=844.2[M-H] -
Accurate mass (Exact Mass): 845.2
Figure BSA00000408378500271
(embodiment 4)
After in 10.0 parts of 2-amino-5-nitrobenzoic acids, adding 70 parts of water, add 2.4 parts of sodium hydroxide again, obtain yellow suspension liquid.Add 11.3 parts of Sodium Nitrites down ice-cooled, then little by little add 35.2 part 35% hydrochloric acid.Afterwards, stirred 3.5 hours down,, add 120 part 9% thionamic acid aqueous solution stir about 10 minutes at leisure, obtain containing the suspension liquid of diazonium salt for the excessive nitrous acid of cooling fast ice-cooled.
Then, make the compound shown in 11.8 parts of formulas (c-3) outstanding turbid in 85 parts of water, use sodium hydroxide that pH is adjusted into 9.0.At this moment, keep the above-mentioned pH value that contains the diazonium salt suspension liquid in 7.5～9.5 scopes, it is lasted 1 hour use pump drip.After dripping end, further at room temperature stir and obtained the xanchromatic suspension liquid in 2 hours.At 60 ℃ of yellow solids that following dry filter obtains of decompression, obtain the compound shown in 15.9 parts of formulas (d-4).By 1H-NMR confirms its structure.
The evaluation of compound shown in the formula (d-4)
1H-NMR (500MHz, δ value (ppM, TMS benchmark), DMSO-d 6): 1.14 (3H, t), 2.24 (3H, s), 3.86 (2H, dd), 7.69 (2H, dd), 8.06 (1H, d), 8.40 (1H, dd), 8.67 (1H, d), 15.3 (1H, s).
Figure BSA00000408378500272
In the compound shown in 5.0 parts of formulas (d-4), add 150 parts of N-Methyl pyrrolidone be heated to 50 ℃ make it dissolving after, add 1.8 parts of formic acid chromium n hydrates, after 120 ℃ of following stir abouts 2 hours, added 0.6 part of yellow soda ash stir about again 3 hours, obtain dark orange solution.This solution is injected 20% salt solution, after the orange solids of filtration gained,, obtain the compound (productive rate 53%) shown in 2.9 parts of formulas (I-4) 60 ℃ of following vacuum-dryings.
The evaluation of the compound shown in the formula (I-4)
(mass analysis) ionization pattern=ESI-:m/z=826.1[M-Na] -
Accurate mass (Exact Mass): 849.1
Figure BSA00000408378500281
(embodiment 5)
After in 5.5 parts of anthranilic acids, adding 88 parts of water, add 3.2 parts of sodium hydroxide again and obtain yellow suspension liquid.Add 8.9 parts of Sodium Nitrites down ice-cooled, then little by little add 33.2 part 35% hydrochloric acid.Afterwards, stirred 3 hours down,, add 100 part 9% thionamic acid aqueous solution stir about 10 minutes at leisure, obtain containing the suspension liquid of diazonium salt for the excessive nitrous acid of cooling fast ice-cooled.
On the other hand, mix 26.0 parts of ethyl 3-oxobutanoates (Tokyo changes into industry (strain) system), 20.8 parts of methyl-cyanacetates (the Tokyo system of changing into) and 24.4 parts of 2-monoethanolamines (with the pure pharmaceutical worker's industry of light (strain) system), stirred 24 hours down in 95 ℃.After above-mentioned reaction solution is cooled to room temperature, join in the mixed solution of 304 parts of water, 35 part of 35% hydrochloric acid, at room temperature stirred 1 hour.Carry out drying after obtaining the crystal that the residue of suction filtration promptly separates out, obtain the compound shown in 20.4 parts of formulas (c-4).
Figure BSA00000408378500282
Then, make the compound shown in 8.5 parts of formulas (c-4) outstanding turbid in 77 parts of water, use sodium hydroxide that pH is adjusted into 9.0.At this moment, keep the above-mentioned pH value that contains the diazonium salt suspension liquid in 8.0～9.5 scopes, it is lasted 1 hour use pump drip.After dripping end, further under room temperature, stirred 2 hours, obtain the xanchromatic suspension liquid.At 60 ℃ of yellow solids that following dry filter obtains of decompression, obtain the compound shown in 11.2 parts of formulas (d-5).By 1H-NMR confirms its structure.
The evaluation of compound shown in the formula (d-5)
1H-NMR (270MHz, δ value (ppM, TMS benchmark), DMSO-d 6): 2.56 (3H, s), 3.52 (2H, t), 3.93 (2H, t), 4.82 (1H, brs), 7.36 (1H, t), 7.74 (1H, t), 8.02-8.06 (1H, 1H, overlapped), 15.7 (1H, s).
Figure BSA00000408378500291
In the compound shown in 10 parts of formulas (d-5), add 150 parts of dinethylformamides, 7.7 parts of chromium ammonium suplhates, 2.6 parts of sodium-acetates,, obtain dark orange solution in 135 ℃ of following stir abouts 6 hours.This solution is injected 20% salt solution, filter the orange solids of gained,, obtain the compound (productive rate 73%) shown in 8.0 parts of formulas (I-5) 60 ℃ of following vacuum-dryings.
The evaluation of the compound shown in the formula (I-5)
(mass analysis) ionization pattern=ESI-:m/z=732.1[M-Na] -
Accurate mass (Exact Mass): 755.1
(embodiment 6)
After in 19.4 parts of 5-(N-kharophen) anthranilic acid (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 20.4 parts of formulas (c-4) 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 the xanchromatic suspension liquid.Stirred 1 hour.At 60 ℃ of yellow solids that following dry filter obtains of decompression, obtain the compound shown in 39.1 parts of formulas (d-6).
Figure BSA00000408378500301
Then, add the chloro-acid shown in 32.5 parts of formulas (e-1) (with the pure pharmaceutical worker's industry of light (strain) system) in the compound shown in 39.9 parts of formulas (d-6), in N-Methyl pyrrolidone, 70 ℃ were stirred 3 hours down.Reaction is poured in the water after finishing, and obtains the compound shown in 50.1 parts of formulas (d-7).The compound of gained presents orange, tests maximum absorption wavelength (λ max) in the ethyl lactate solvent, and its result is shown as 459nm.In addition, by 1H-NMR confirms its structure.
1H-NMR：0.72(3H，m)，0.75(3H，m)，1.02(2H，m)，1.07(2H，m)，1.23(2H，m)，1.31(2H，m)，2.06(3H，s)，2.11(1H，m)，4.10(2H，m)，4.24(2H，m)，7.88(1H，m)，7.92(1H，m)，8.32(1H，d)，10.26(1H，s)，15.63(1H，s)。
Figure BSA00000408378500302
In the compound shown in 10.0 parts of formulas (d-7), add 150 parts of dinethylformamides, 7.7 parts of chromium ammonium suplhates, 2.6 parts of sodium-acetates,, obtain dark orange solution in 135 ℃ of following stir abouts 6 hours.This solution is injected 20% salt solution, filter the orange solids of gained,, obtain the compound shown in 4.9 parts of formulas (I-143) 60 ℃ of following vacuum-dryings.
Figure BSA00000408378500311
The evaluation of the compound shown in the formula (I-143)
(mass analysis) ionization pattern=ESI-:m/z=1098.3[M-Na] -
Accurate mass (Exact Mass): 1121.34
(embodiment 7)
Add 32.4 parts of Benzoyl chlorides (with the pure pharmaceutical worker's industry of light (strain) system) in the compound shown in 30.0 parts of formulas (d-6), in N-Methyl pyrrolidone, 70 ℃ were stirred 3 hours down.Reaction is poured in the water after finishing, and obtains the compound shown in 35.8 parts of formulas (d-8).The compound of gained presents orange, tests maximum absorption wavelength (λ max) in the ethyl lactate solvent, and its result is shown as 459nm.In addition, by 1H-NMR confirms its structure.
1H-NMR：2.70(3H，s)，2.50(3H，s)，4.28(2H，t)，4.44(2H，t)，7.43(1H，t)，7.57(1H，m)，7.89(1H，m)，7.95(1H，m)，8.35(1H，m)，10.27(1H，s)，15.67(1H，s)。
Figure BSA00000408378500312
Then, in the compound shown in 9.6 parts of formulas (d-8), add 150 parts of dinethylformamides, 7.7 parts of chromium ammonium suplhates, 2.6 parts of sodium-acetates,, obtain dark orange solution in 135 ℃ of following stir abouts 6 hours.This solution is injected 20% salt solution, filter the orange solids of gained,, obtain the compound shown in 7.1 parts of formulas (I-156) 60 ℃ of following vacuum-dryings.
The evaluation of the compound shown in the formula (I-156)
(mass analysis) ionization pattern=ESI-:m/z=1054.20[M-Na] -
Accurate mass (Exact Mass): 1077.19
The mensuration of＜absorbancy 〉
In ethyl lactate, constant volume is 250cm with the 0.35g compound dissolution 3, get 2cm wherein 3Solution dilutes with ethyl lactate, and making volume is 100cm 3, make the solution that concentration is 0.028g/L.Use ultraviolet-visible pectrophotometer (V-650DS, Japanese beam split (strain) system) (quartz container, optical length 1cm) to measure the absorbancy under maximum absorption wavelength (λ max) and the maximum absorption wavelength (λ max) to this solution.The results are shown in Table 2.
[table 2]
Compound λmax(nm) Absorbancy
Embodiment 1 (I-1) 472 1.75
Embodiment 2 (I-2) 471 1.68
Embodiment 3 (I-3) 494 1.28
Embodiment 4 (1-4) 458 1.31
Embodiment 5 (I-5) 465 1.19
Embodiment 6 (I-143) 468 1.23
Embodiment 7 (I-156) 469 1.10
Comparative example 1 (R-1) 436 0.84
In the table, compound (R-1) is C.I. solvent yellow 21 (Oleosol Fast Yellow 2G: ridge, field chemical industry (strain) system).
(embodiment 8)
[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: 680 parts of ethyl lactates
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 9)
Except synthetic compound (I-1) among the embodiment 1 being replaced with among the embodiment 2 the synthetic compound (I-2), carry out the experiment identical with embodiment 8, obtain colored resin composition and colour filter.
(embodiment 10)
Except synthetic compound (I-1) among the embodiment 1 being replaced with among the embodiment 3 the synthetic compound (I-3), carry out the experiment identical with embodiment 8, obtain colored resin composition and colour filter.
(embodiment 11)
Except synthetic compound (I-1) among the embodiment 1 being replaced with among the embodiment 4 the synthetic compound (I-4), carry out the experiment identical with embodiment 8, obtain colored resin composition and colour filter.
(embodiment 12)
Except synthetic compound (I-1) among the embodiment 1 being replaced with among the embodiment 5 the synthetic compound (I-5), carry out the experiment identical with embodiment 8, obtain colored resin composition and colour filter.
(embodiment 13)
Except synthetic compound (I-1) among the embodiment 1 being replaced with among the embodiment 6 the synthetic compound (I-143), carry out the experiment identical with embodiment 8, obtain colored resin composition and colour filter.
(embodiment 14)
Except synthetic compound (I-1) among the embodiment 1 being replaced with among the embodiment 7 the synthetic compound (I-156), carry out the experiment identical with embodiment 8, obtain colored resin composition and colour filter.
As can be known from the results of Table 2, compound absorbancy height of the present invention demonstrates high branch optical concentration.In addition, the colored resin composition that contains this compound has excellent color characteristics, can be used to make high-quality colour filter.
Utilizability on the industry
Compound of the present invention is applicable to dyestuff. Compound of the present invention divides the optical concentration height because molar absorptivity coefficient height, so can be used for using as dyestuff such as the colour filter device of the display unit such as, liquid crystal display device.

Claims (8)

1. the compound shown in the formula (0),
Figure FSA00000408378400011
In the formula (0), R 11 valency saturated hydrocarbyl of expression carbonatoms 1～8, the hydrogen atom that this saturated hydrocarbyl comprised can be by-OR 8,-COOR 8,-OCOR 8,-CONR 8R 9, 1 valency aromatic hydrocarbyl of carbonatoms 6～10 or halogen atom replace, this saturated hydrocarbyl is contained-CH 2-among not with-O-bonding-CH 2-can be replaced by-CO-;
R 2The expression hydrogen atom ,-CN or-CONH 2Base;
R 3The alkyl of the carbonatoms 1～4 that expression can be replaced by halogen atom;
R 4a～R 7aExpression-R independently of each other 8,-OR 8,-COOR 8,-COR 8,-OCOOR 8,-OCOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K ,-SO 2NR 8R 9Perhaps-NR 11R 12, R 4aAnd R 5a, R 5aAnd R 6aAnd R 6aAnd R 7aBonding forms 6～7 yuan of rings that contain phenyl ring carbon mutually;
R 8And R 9Represent 1 valency aliphatic alkyl of hydrogen atom, carbonatoms 1～8, the aralkyl of carbonatoms 7～12 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10 independently of each other, the hydrogen atom that this aliphatic alkyl, this aralkyl and this aromatic hydrocarbyl comprised can be by-OR 10Replace;
R 10Expression hydrogen atom, 1 valency saturated hydrocarbyl of carbonatoms 1～8 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10;
R 11And R 12Represent 1 valency aliphatic alkyl of hydrogen atom, carbonatoms 1～8, the acyl group or the tetrahydrofurfuryl of carbonatoms 2～8 independently of each other, R 11And R 12Bonding forms the ring that contains nitrogen-atoms mutually;
A +The tetra-allkylammonium positive ion of expression hydrogen positive ion, sodium positive ion, potassium positive ion or carbonatoms 1～4.
2. the compound shown in the formula (I),
Figure FSA00000408378400021
In the formula (I), R 11 valency saturated hydrocarbyl of expression carbonatoms 1～8, the hydrogen atom that this saturated hydrocarbyl comprised can be by-OR 8,-COOR 8,-OCOR 8,-CONR 8R 9, 1 valency aromatic hydrocarbyl of carbonatoms 6～10 or halogen atom replace, this saturated hydrocarbyl is contained-CH 2-among not with-O-bonding-CH 2-can be replaced by-CO-;
R 2The expression hydrogen atom ,-CN or-CONH 2
R 3The alkyl of expression hydrogen atom, the carbonatoms 1～4 that can be replaced by halogen atom;
R 4～R 7Expression-R independently of each other 8,-OR 8,-COOR 8,-CN ,-NO 2, halogen atom ,-SO 3H ,-SO 3Na ,-SO 3K or-SO 2NR 8R 9
R 8And R 9Represent 1 valency aliphatic alkyl of hydrogen atom, carbonatoms 1～8, the aralkyl of carbonatoms 7～12 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10 independently of each other, the hydrogen atom that this aliphatic alkyl, this aralkyl and this aromatic hydrocarbyl comprised can be by-OR 10Replace;
R 10Expression hydrogen atom, 1 valency saturated hydrocarbyl of carbonatoms 1～8 or 1 valency aromatic hydrocarbyl of carbonatoms 6～10;
A +The tetra-allkylammonium positive ion of expression hydrogen positive ion, sodium positive ion, potassium positive ion or carbonatoms 1～4.
3. compound according to claim 1 and 2, R 1For can by-OH-or-OCOR 81 valency saturated hydrocarbyl of the carbonatoms 1～8 that replaces.
4. according to claim 2 or 3 described compounds, R 4～R 7In have 3 at least for hydrogen atom.
5. compound according to claim 1 and 2, R 2For-CN.
6. a dyestuff is an effective constituent with claim 1 or 2 described compounds.
7. a colored resin composition contains the described dyestuff of claim 6, resin and solvent.
8. according to claim 3 or 4 described compounds, R 2For-CN.
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