CN101620379A - Coloring light-sensitive resin composition - Google Patents

Coloring light-sensitive resin composition Download PDF

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CN101620379A
CN101620379A CN200910158440A CN200910158440A CN101620379A CN 101620379 A CN101620379 A CN 101620379A CN 200910158440 A CN200910158440 A CN 200910158440A CN 200910158440 A CN200910158440 A CN 200910158440A CN 101620379 A CN101620379 A CN 101620379A
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carbon number
expression
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formula
hydrogen atom
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城内由子
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to CN201610213574.6A priority Critical patent/CN105652596B/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Abstract

A coloring light-sensitive resin composition contains colorant (A), adhesive resin (B), optical polymeric compound (C), optical polymeric initiator (D) and solvent (E), wherein the colorant (A) contains organic solvent dissoluble dye with a compound represented by formula (I), and organic pigments.

Description

Photosensitive composition
Technical field
The color filter that the present invention relates to photosensitive composition and use this photosensitive composition, this photosensitive composition are applicable to the formation of the rendered image that constitutes the used color filter of liquid crystal display cells or solid-state imager.
Background technology
In recent years, wish that the color filter height becomes more meticulous, high brightnessization, high-contrastization, in order to reach these requirements, along with the development of the high color purityization of color filter, the pigment concentration in the photosensitive composition has the tendency that uprises., this pigment concentration uprises, and pigment has certain particle diameter, makes light scattering, so there is the low problem of contrast of the color filter that uses the photosensitive composition formation that contains this pigment.
Therefore, particularly, for example disclose by be used in combination as an extinction manifest color dyestuff the sour cyanine compound in pyrazoles system side and as blue pigment Pigment Blue (P.B) 15:6 of pigment, reach the high-contrastization (patent documentation 1) of color filter.
Patent documentation 1: the Jap.P. spy opens the 2006-079012 communique
Summary of the invention
Further, in order to reach the high brightnessization of color filter, except patent documentation 1 concrete disclosed combination, wish that also exploitation contains the dyestuff of other combinations and the photosensitive composition of pigment.
The inventor is in order to solve above-mentioned problem, and studies, and found that the photosensitive composition that contains certain dyestuff and pigment provides filming of high brightness.
The present invention is a kind of photosensitive composition, contain colorant (A), adhesive resin (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D) and solvent (E), wherein, colorant (A) is to contain the organic solvent soluble dye of the compound that comprises formula (1) expression and the colorant of organic pigment
(in the formula (1), R 1～R 4Represent independently of one another hydrogen atom ,-R 6The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 6,-OH ,-OR 6,-SO 3 -,-SO 3H ,-SO 3M ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9Replace,
R 5Expression-SO 3 -,-SO 3H ,-SO 3M ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
M represents 0～5 integer, when m is a integer more than 2, and a plurality of R 5Can be the same or different,
X represents halogen atom, and a represents 0 or 1 integer,
R 6The saturated hydrocarbyl of expression carbon number 1～10, the contained hydrogen atom of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can be replaced by halogen atom, the contained methylene of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can by oxygen atom, carbonyl or-NR 6-replace,
R 8And R 9Represent the straight chain of carbon number 1～10 independently of one another or contain side chain alkyl, carbon number 3～30 naphthenic base or-Q, perhaps R 8And R 9Bonding and form the heterocycle of carbon number 1～10 mutually,
Q represents the aromatic hydrocarbyl of carbon number 6～10 or the aromatic heterocycle of carbon number 5～10, above-mentioned aromatic hydrocarbyl and hydrogen atom that aromatic heterocycle is contained can by-OH, R 6,-OR 6,-NO 2,-CH=CH 2,-CH=CHR 6Perhaps halogen atom replaces,
The straight chain of carbon number 1～10 or contain the alkyl of side chain and hydrogen atom that the naphthenic base of carbon number 3～30 is contained can by hydroxyl, halogen atom ,-Q ,-CH=CH 2Perhaps-CH=CHR 6Replace,
The straight chain of carbon number 1～10 or contain the alkyl of side chain and methylene that the naphthenic base of carbon number 3～30 is contained can by oxygen atom, carbonyl or-NR 6-replace,
The contained hydrogen atom of the heterocycle of carbon number 1～10 can be by R 6,-OH or-Q replaces,
M represents sodium atom or potassium atom.)
Again, the present invention is that the compound of formula (1) expression is the above-mentioned photosensitive composition of the compound of formula (1-1) expression.
Figure G2009101584409D00031
(in the formula (1-1), R 11～R 14Represent independently of one another hydrogen atom ,-R 6The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 6,-OH ,-OR 6,-SO 3 -,-SO 3H ,-SO 3Na ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9Replace,
R 15The expression hydrogen atom ,-SO 3 -,-SO 3H ,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
R 16Expression-SO 3 -,-SO 3H ,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
R 6, R 8, R 9, m, X and a represent meaning same as described above.)
Again, the present invention is that the compound of formula (1) expression is the above-mentioned photosensitive composition of the compound of formula (1-2) expression,
Figure G2009101584409D00032
(in the formula (1-2), R 21～R 24Represent independently of one another hydrogen atom ,-R 26The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 26,-OH ,-OR 26,-SO 3 -,-SO 3Na ,-CO 2H ,-CO 2R 26,-SO 3H ,-SO 3R 26Perhaps-SO 2NHR 28Replace,
R 25Expression-SO 3 -,-SO 3Na ,-CO 2H ,-CO 2R 26,-SO 3H or-SO 2NHR 28,
R 26The saturated hydrocarbyl of expression carbon number 1～10, the contained hydrogen atom of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can be by-OR 26Perhaps halogen atom replaces,
R 28The expression hydrogen atom ,-R 26,-CO 2R 26The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can be by-R 26Perhaps-OR 26Replace,
M, X and a represent meaning same as described above.)
Again, the present invention is that the compound of formula (1) expression is the above-mentioned photosensitive composition of the compound of formula (1-3) expression,
Figure G2009101584409D00041
(in the formula (1-3), R 31And R 32Represent phenyl independently of one another, the contained hydrogen atom of above-mentioned phenyl can by halogen atom ,-R 26,-OR 26,-CO 2R 26,-SO 3R 26Perhaps-SO 2NHR 28Replace,
R 33Expression-SO 3 -Perhaps-SO 2NHR 28,
R 34The expression hydrogen atom ,-SO 3 -Perhaps-SO 2NHR 28,
R 26, R 28, X and a represent meaning same as described above.)
Again, the present invention is that the compound of formula (1) expression is the above-mentioned photosensitive composition of the compound of formula (1-4) expression,
Figure G2009101584409D00042
(in the formula (1-4), R 41And R 42Represent phenyl independently of one another, the contained hydrogen atom of above-mentioned phenyl can be by-R 26Perhaps-SO 2NHR 28Replace,
R 43Expression-SO 3 -Perhaps-SO 2NHR 28,
R 26, R 28, X and a represent meaning same as described above.)
Again, the present invention is that organic pigment is to contain the C.I. pigment blue 15: the above-mentioned photosensitive composition of 6 organic pigment.
Again, the present invention is the C.I. pigment blue 15 in the colorant (A): 6 with the mass ratio of the organic solvent soluble dye of the compound that contains formula (1) expression be 97: 3～50: 50 above-mentioned photosensitive composition.
Again, the present invention is a kind of filming, and it uses above-mentioned photosensitive composition to form.
Again, the present invention is a kind of color filter, and it uses above-mentioned photosensitive composition to form.
Again, the present invention is the above-mentioned color filter that forms by photo-engraving process.
Embodiment
Photosensitive composition of the present invention contains colorant (A), and colorant (A) is the colorant of the organic solvent soluble dye that contains the compound that comprises formula (1) expression (below be sometimes referred to as " dyestuff (1) ").
Dyestuff (1) can be selected according to the color of purpose color filter, also can mix multiple dyestuff and use.Dyestuff (1) preferably has sufficient solubleness in the contained solvent in photosensitive composition, have sufficient solubleness with the degree that can form pattern in the developing procedure when pattern forms in developer solution.
Figure G2009101584409D00051
(in the formula (1), R 1～R 4Represent independently of one another hydrogen atom ,-R 6The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 6,-OH ,-OR 6,-SO 3 -,-SO 3H ,-SO 3M ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9Replace,
R 5Expression-SO 3 -,-SO 3H ,-SO 3M ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
M represents 0～5 integer, when m is a integer more than 2, and a plurality of R 5Can be the same or different,
X represents halogen atom, and a represents 0 or 1 integer,
R 6The saturated hydrocarbyl of expression carbon number 1～10, the contained hydrogen atom of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can be replaced by halogen atom, the contained methylene of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can by oxygen atom, carbonyl or-NR 6-replace,
R 8And R 9Represent the straight chain of carbon number 1～10 independently of one another or contain side chain alkyl, carbon number 3～30 naphthenic base or-Q, perhaps R 8And R 9Bonding and form the heterocycle of carbon number 1～10 mutually,
Q represents the aromatic hydrocarbyl of carbon number 6～10 or the aromatic heterocycle of carbon number 5～10, the contained hydrogen atom of above-mentioned aromatic hydrocarbyl and aromatic heterocycle can by-OH, R 6,-OR 6,-NO 2,-CH=CaH 2,-CH=CHR 6Perhaps halogen atom replaces,
The straight chain of carbon number 1～10 or contain the alkyl of side chain and hydrogen atom that the naphthenic base of carbon number 3～30 is contained can by hydroxyl, halogen atom ,-Q ,-CH=CH 2Perhaps-CH=CHR 6Replace,
The straight chain of carbon number 1～10 or contain the alkyl of side chain and methylene that the naphthenic base of carbon number 3～30 is contained can by oxygen atom, carbonyl or-NR 6-replace,
The contained hydrogen atom of the heterocycle of carbon number 1～10 can be by R 6,-OH or-Q replaces,
M represents sodium atom or potassium atom.)
R 6Methyl, ethyl, propyl group, isopropyl, butyl, isobutyl, amyl group, isopentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, suberyl, octyl group, 2-ethylhexyl, ring octyl group, nonyl, decyl (decanyl), three ring decyls, methoxy-propyl, ethoxycarbonyl propyl, own oxygen base propyl group, 2-ethyl hexyl oxy propyl group, methoxyl hexyl, ethoxycarbonyl propyl etc. are arranged for example.
The aromatic hydrocarbyl of carbon number 6～10 has phenyl, naphthyl etc. for example.
As the substituting group of the aromatic hydrocarbyl of this carbon number 6～10 for the halogen atom of example, fluorine, chlorine, bromine etc. are arranged for example.
-SO 3R 6Mesyl, ethylsulfonyl, own sulfonyl, last of the ten Heavenly stems sulfonyl etc. is arranged for example.
-CO 2R 6Methyl oxygen base carbonyl is arranged for example, ethyl oxygen base carbonyl, propyl group oxygen base carbonyl, isopropyl oxygen base carbonyl, butyl oxygen base carbonyl, isobutyl oxygen base carbonyl, amyl group oxygen base carbonyl, isopentyl oxygen base carbonyl, neopentyl oxygen base carbonyl, the cyclopentyloxy carbonyl, hexyl oxygen base carbonyl, cyclohexyl oxygen base carbonyl, heptyl oxygen base carbonyl, suberyl oxygen base carbonyl, octyl group oxygen base carbonyl, 2-ethylhexyl oxygen base carbonyl, ring octyl group oxygen base carbonyl, nonyl oxygen base carbonyl, decyl (decanyl) oxygen base carbonyl, three ring decyl (decanyl) oxygen base carbonyls, methoxy-propyl oxygen base carbonyl, ethoxycarbonyl propyl oxygen base carbonyl, own oxygen base propyl group oxygen base carbonyl, 2-ethyl hexyl oxy propyl group oxygen base carbonyl, methoxyl hexyl oxygen base carbonyl etc.
-SO 2NHR 8Sulfamoyl is arranged for example; the methane sulfamoyl; the ethane sulfamoyl; the propane sulfamoyl; different propane sulfamoyl; the butane sulfamoyl; the isobutane sulfamoyl; the pentane sulfamoyl; the isopentane sulfamoyl; the neopentane sulfamoyl; the cyclopentane sulfamoyl; the hexane sulfamoyl; the cyclohexane sulfamoyl; the heptane sulfamoyl; the cycloheptane sulfamoyl; the octane sulfamoyl; 2-ethyl hexane sulfamoyl; 1,5-dimethylhexane sulfamoyl; the cyclooctane sulfamoyl; the nonane sulfamoyl; the decane sulfamoyl; the tristane sulfamoyl; the methoxy propane sulfamoyl; the ethoxy propane sulfamoyl; propoxyl group propane sulfamoyl; isopropoxy propane sulfamoyl; own oxygen base propane sulfamoyl; 2-ethyl hexyl oxy propane sulfamoyl; the methoxyhexane sulfamoyl; 3-phenyl-1-methylpropane sulfamoyl etc.
-SO 2NHR 8And-SO 2NR 8R 9The group that also has following formula to represent for example.
Figure G2009101584409D00071
In the above-mentioned formula, X 1The expression halogen atom.X 1In halogen atom fluorine atom, chlorine atom and bromine atoms are arranged for example.
In the above-mentioned formula, X 3Expression alkyl of carbon number 1～3 or carbon number 1～alkoxy, the hydrogen atom of this alkyl and alkoxy can be replaced by halogen atom.
The alkyl of the carbon number 1～3 that can be replaced by halogen atom has methyl, ethyl, propyl group, isopropyl, perfluoro-methyl etc. for example.
The alkoxy of the carbon number 1～3 that can be replaced by halogen atom has methoxyl, ethoxy, propoxyl group etc. for example.
Figure G2009101584409D00091
Figure G2009101584409D00092
Figure G2009101584409D00101
In the above-mentioned formula, X 2Alkyl, the alkoxy of carbon number 1～3, halogen atom, the nitro of expression carbon number 1～3, the hydrogen atom of this alkyl and alkoxy can be replaced by halogen atom.
X 2In halogen atom fluorine atom, chlorine atom and bromine atoms are arranged for example.
The alkyl of the carbon number 1～3 that can be replaced by halogen atom has methyl, ethyl, propyl group, isopropyl, perfluoro-methyl etc. for example.
The alkoxy of the carbon number 1～3 that can be replaced by halogen atom has methoxyl, ethoxy, propoxyl group etc. for example.
Figure G2009101584409D00102
Figure G2009101584409D00111
Figure G2009101584409D00121
In the above-mentioned formula, X 2The meaning of expression is same as described above.
Figure G2009101584409D00122
Figure G2009101584409D00131
In the above-mentioned formula, X 3The meaning of expression is same as described above.
-SO 2NR 8R 9Contained R 8And R 9The branch-like alkyl of preferred carbon number 6～8, ester ring type alkyl, allyl, phenyl, the aralkyl of carbon number 8～10, the hydroxyl alkyl of carbon number 2～8 and the alkyl or aryl that contains alkoxy of aryl or carbon number 2～8 of carbon number 5～7, especially preferred 2-ethylhexyl.
The preferred ethyl of the substituting group of the aromatic hydrocarbyl of carbon number 6～10, propyl group, phenyl, 3,5-dimethylphenyl ,-SO 3R 6Perhaps-SO 2NHR 8
Aromatic hydrocarbyl with substituent carbon number 6～10 has aminomethyl phenyl, 3,5-dimethylphenyl, trimethylphenyl, ethylphenyl, hexyl phenyl, decyl phenyl, fluorobenzene, chlorobenzene, bromobenzene, hydroxy phenyl, methoxyphenyl, Dimethoxyphenyl, ethoxyl phenenyl, own oxygen base phenyl, last of the ten Heavenly stems oxygen base phenyl, trifluoromethyl etc. for example.
R 1And R 2In one of at least or R 3And R 4In the alkyl of one of at least preferred carbon number 1～4 or aromatic hydrocarbyl that can substituted carbon number 6～10.
R 1And R 2In one of at least and R 3And R 4In the alkyl of one of at least preferred carbon number 1～4 or aromatic hydrocarbyl that can substituted carbon number 6～10.
R 1And R 2In one of at least and R 3And R 4In one of at least more preferably can substituted carbon number 6～10 aromatic hydrocarbyl.
R 5Be preferably carboxyl, ethyl oxygen base carbonyl, sulfinyl, 2-ethyl hexyl oxy propane sulfamoyl, 1,5-dimethylhexane sulfamoyl, 3-phenyl-1-methylpropane sulfamoyl, isopropoxy propane sulfamoyl.
The compound of compound preferred formula (1-1) expression of formula (1) expression,
Figure G2009101584409D00141
(in the formula (1-1), R 11～R 14Represent independently of one another hydrogen atom ,-R 6The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 6,-OH ,-OR 6,-SO 3 -,-SO 3H ,-SO 3Na ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9Replace,
R 15The expression hydrogen atom ,-SO 3 -,-SO 3H ,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
R 16Expression-SO 3 -,-SO 3H ,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
R 6, R 8, R 9, the meaning represented of m, X and a is same as described above.)
The compound of compound preferred formula (1-2) expression of formula (1) expression,
Figure G2009101584409D00142
((in the formula (1-2), R 21～R 24Represent independently of one another hydrogen atom ,-R 26The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 26,-OH ,-OR 26,-SO 3 -,-SO 3Na ,-CO 2H ,-CO 2R 26,-SO 3H ,-SO 3R 26Perhaps-SO 2NHR 28Replace,
R 25Expression-SO 3 -,-SO 3Na ,-CO 2H ,-CO 2R 26,-SO 3H or-SO 2NHR 28,
R 26The saturated hydrocarbyl of expression carbon number 1～10, the contained hydrogen atom of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can be by-OR 26Perhaps halogen atom replaces,
R 28The expression hydrogen atom ,-R 26,-CO 2R 26The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can be by-R 26Perhaps-OR 26Replace,
The meaning that m, X and a represent is same as described above.)
The compound of compound preferred formula (1-3) expression of formula (1) expression,
Figure G2009101584409D00151
(in the formula (1-3), R 31And R 32Represent phenyl independently of one another, the contained hydrogen atom of above-mentioned phenyl can by halogen atom ,-R 26,-OR 26,-CO 2R 26,-SO 3R 26Perhaps-SO 2NHR 28Replace,
R 33Expression-SO 3 -Perhaps-SO 2NHR 28,
R 34The expression hydrogen atom ,-SO 3 -Perhaps-SO 2NHR 28,
R 26, R 28, the meaning represented of X and a is same as described above.)
The compound of compound preferred formula (1-4) expression of formula (1) expression,
Figure G2009101584409D00152
(in the formula (1-4), R 41And R 42Represent phenyl independently of one another, the contained hydrogen atom of above-mentioned phenyl can be by-R 26Perhaps-SO 2NHR 28Replace,
R 43Expression-SO 3 -Perhaps-SO 2NHR 28,
R 26, R 28, X and a represent meaning same as described above.)
The compound of formula (1) expression has for example compound of formula (1a)～formula (1f) expression for example.
Figure G2009101584409D00153
(in the formula (1a), R bAnd R cRepresent independently respectively hydrogen atom ,-SO 3 -,-CO 2H or-SO 2NHR aR aExpression 2-ethylhexyl.The meaning that X and a represent is same as described above.)
Figure G2009101584409D00161
(in the formula (1b), R bThe meaning of expression is same as described above.)
The compound of formula (1b) expression is the dynamic isomer of the compound of formula (1b-1) expression.
Figure G2009101584409D00162
(in the formula (1b-1), R b, the meaning represented of X and a is same as described above.)
Figure G2009101584409D00163
(in formula (1c) and the formula (1d), R d, R cAnd R fDifference is expression-SO independently 3 -,-SO 3Na or-SO 2NHR aR aExpression 2-ethylhexyl.)
Figure G2009101584409D00164
(in formula (1e) and the formula (1f), R g, R hAnd R iRepresent independently respectively hydrogen atom ,-SO 3 -,-SO 3H or-SO 2NHR aR aExpression 2-ethylhexyl.)
Compound for formula (1) expression can obtain by the following method, for example by conventional method to having-SO 3The pigment of H or pigment intermediate carry out chlorination, make having-SO of obtaining again 2The pigment of Cl or pigment intermediate and R 8-NH 2The amine reaction of expression.Also can obtain, make a kind of pigment,, make it then to react with amine with this pigment and above-mentioned the same ground chlorination by the method that the upper right hurdle～hurdle, lower-left of the 3rd page in Japanese patent laid-open 3-78702 communique is put down in writing by such method.
Colorant (A) is except containing dyestuff (1), also contains the colorant of organic pigment.
As organic pigment, for example have for example particularly: C.I. pigment blue 15,15:3,15:4,15:6, blue pigments such as 60; C.I. pigment violet 1,19,23,29,32,36, violet pigment of 38 etc. etc.Wherein, preferably contain and be selected from C.I. pigment Violet 23, C.I. pigment blue 15: 3, at least a pigment of 15:6, especially preferably contain the C.I. pigment blue 15: 6.These pigment may be used alone, can also be two or more kinds in combination.
As required, can handle or utilize the cleaning treatment of removing organic solvent that impurity uses or water etc. to the micronize that above-mentioned organic pigment carry out that the surface treatment that imports pigment derivative that acidic groups or basic group are arranged etc. is handled, used to rosin, sulfuric acid micronize method is handled, utilized in the grafting that utilizes macromolecular compound that surface of pigments is carried out etc. and carries out, utilize the processing of removing ionic impurity of ion exchange process etc. etc.
Preferably, the uniform particle diameter of organic pigment.Carry out dispersion treatment by making it to contain pigment dispersing agent, can obtain the dispersible pigment dispersion that pigment is dispersed in state such in the solution equably.
Surfactants such as kation system, negative ion system, nonionic system, both sexes, polyester system, polyamine system, acrylic acid series etc. are arranged for example as above-mentioned pigment dispersing agent.Can only use a kind, also can be used in combination more than 2 kinds.
When using pigment dispersing agent, in the pigment of per 1 mass parts (A), below preferred 1 mass parts of its use amount, more preferably 0.05 mass parts above, below 0.5 mass parts.The use amount of pigment dispersing agent can obtain the dispersible pigment dispersion of disperse state equably when above-mentioned scope, thereby desirable.
The content of colorant (A) is with respect to the solid constituent in the photosensitive composition, in massfraction, and preferred 5～60 quality %, more preferably 8～55 quality %, further preferred 10～50 quality %.Here, solid constituent points to the total of the composition except that desolvating in the color sensation photosensitive resin composition.
The content of colorant (A) is when above-mentioned scope, and the colour saturation when making color filter is abundant, and can make the adhesive polymer that contains necessary amount in the composition, therefore can form the sufficient pattern of physical strength, thereby desirable.
The content of the dyestuff (1) in the colorant (A) is 3～80% by quality ratio, preferred 3～70 quality %, more preferably 3～50 quality %.
The content of the organic pigment in the colorant (A) is 20～97% usually by quality ratio, preferred 30～97 quality %, more preferably 50～97 quality %.
Especially, preferably the mass ratio of C.I. pigment blue 1 5:6 and dyestuff (1) is 97: 3～50: 50.
When the content of the organic pigment in the colorant (A) during in above-mentioned scope, it is easy to penetrate the spectrum optimization, and owing to obtain high-contrast, high brightness, thereby good, and thermotolerance, drug resistance are good, therefore more satisfactory.
The photosensitive composition that is used to make color filter of the present invention contains adhesive resin (B).Above-mentioned adhesive resin (B) preferably contains the formation unit of deriving out from (methyl) acrylic acid.Here, (methyl) acrylic acid is represented acrylic acid and/or methacrylic acid.Content from the formation unit that above-mentioned (methyl) acrylic acid derives out, in the mole fraction in the total formation unit that constitutes adhesive resin (B), preferred 16 moles of % are above, 40 moles below the %, more preferably 18 moles of % above, 38 moles below the %.From the content of the formation unit that (methyl) acrylic acid derives out in above-mentioned scope, have the favorable solubility of the non-pixel portions when developing and develop after non-pixel portions be difficult to the tendency of residual residue, thereby desirable.
Other monomers as the formation unit that derives adhesive resin except that the formation unit of deriving out from (methyl) acrylic acid have aromatic ethenyl compound for example; unsaturated carboxylate type; unsaturated carboxylic acid aminoalkyl ester class; unsaturated carboxylic acid ethylene oxidic ester class; the vinyl carboxylates class; unsaturated ether; vinyl cyanide (vinyl cyanide) compound; the unsaturated acyl amine; unsaturated imines class; the aliphatics conjugated diene; the macromonomer class that on the end of polymer molecular chain, has single acryloyl group or monomethyl acryloyl group; the unit of the unit of formula (II) expression or formula (III) expression etc.
(in formula (II) and the formula (III), R 53And R 55Represent hydrogen atom or methyl independently of one another, R 54And R 56The alkyl of representing hydrogen atom or carbon number 1～6 independently of one another.)
As above-mentioned adhesive resin, particularly, the constituent of methacrylic acid/benzyl methacrylate multipolymer, methacrylic acid/benzyl methacrylate/styrol copolymer, methacrylic acid/benzyl methacrylate/isobornyl methacrylate multipolymer, methacrylic acid/styrene/methacrylic acid benzyl ester/N-phenylmaleimide multipolymer, methacrylic acid/formula (II) expression (wherein, here, R in the formula (II) 53The expression methyl, R 54The expression hydrogen atom)/and the constituent of benzyl methacrylate multipolymer, formula (II) expression (wherein, here, R in the formula (II) 53The expression methyl, R 54The expression hydrogen atom)/and the constituent of benzyl methacrylate multipolymer, methacrylic acid/formula (III) expression (wherein, here, R in the formula (III) 55The expression methyl, R 56The expression hydrogen atom)/styrol copolymer/methacrylic acid three ring ester copolymers in the last of the ten Heavenly stems etc. are more satisfactory.
The acid number of adhesive resin used in the present invention (B) is generally 50～150, and preferred 60～135, especially preferred 70～135.Above-mentioned acid number has following tendency in above-mentioned scope: the dissolubility for developer solution improves, and unexposed portion becomes and easily dissolves, and high sensitivityization, and the pattern of exposure portion is residual during development, and residual film ratio improves, thereby desirable.Here, acid number be as in and the amount (mg) of the needed potassium hydroxide of 1g acrylic acid series polymeric compounds and the value that is measured to can obtain by using potassium hydroxide aqueous solution carry out titration usually.
The content of adhesive resin (B) in massfraction, is generally 7～65 quality % with respect to the solid constituent in the photosensitive composition, preferred 13～60 quality %, more preferably 17～55 quality %.The content of adhesive resin (B) has to form the tendency that pattern and exploring degree and residual film ratio improve in above-mentioned scope, thereby desirable.
Have the adhesive resin of the constituent of formula (II) expression, the constituent of for example methacrylic acid/formula (II) expression (wherein, here, in the formula (II), R 53The expression methyl, R 54The expression hydrogen atom)/and constituent that the benzyl methacrylate multipolymer can be by representing 2 composition polymkeric substance and formula (IV) (wherein, here, in the formula (IV), R 57The expression hydrogen atom) reaction and obtaining, described 2 composition polymkeric substance are obtained by methacrylic acid and benzyl methacrylate polymerization.
Figure G2009101584409D00191
The constituent of methacrylic acid/formula (III) expression (wherein, here, in the formula (III), R 55The expression methyl, R 56The expression hydrogen atom)/styrol copolymer/methacrylic acid three ring ester copolymers in the last of the ten Heavenly stems can make the monomethacrylates multipolymer of benzyl methacrylate, methacrylic acid, tricyclodecane skeleton react with glycidyl methacrylate and obtain.
The weight-average molecular weight with polystyrene conversion of adhesive resin is generally 5,000～35, and 000, preferred 6,000～30,000, preferred especially 7,000～28,000.Molecular weight is in above-mentioned scope, owing to hardness of film raising, also high, the unexposed portion of residual film ratio are arranged for the favorable solubility of developer solution, the tendency that the exploring degree improves, so desirable.
Especially, from the viewpoint of curable, development, the adhesive resin (B) of preferred formula (V) expression.
Figure G2009101584409D00192
Copolymerization generally uses polymerization initiator to carry out in solvent.Polymerization initiator for example uses 2,2 '-azobis isobutyronitrile or 2, and the two azo-compounds such as (2 Methylpropionic acid methyl esters) of 2 '-azo, or the such superoxide of benzoyl peroxide or tert-butyl peroxide etc.Again, solvent is so long as dissolve the solvent of each monomer and get final product, and uses pure ether-ether class of pure ether-ether classes such as ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters etc. for example etc.Temperature of reaction considers that decisions such as the decomposition temperature of polymerization initiator or the boiling point of solvent and monomer get final product.In addition, also can carry out modification and make photosensitive adhesive resin (B) with the side chain of the compound with polymerizable group to the multipolymer that obtains like this.At this moment, can add the catalyzer that is used in resin, importing polymerizable group.Catalyzer has for example three (dimethylaminomethyl) phenol for example.Can add the adjuvant that is used for preventing subsidiary reaction again.Adjuvant has for example quinhydrones for example.
Photosensitive composition of the present invention contains optical polymerism compound (C).Optical polymerism compound (C) is the living radical that utilizes Photoepolymerizationinitiater initiater (D) to be produced by rayed, acid etc. and can polymeric compounds, and the compound of the carbon-to-carbon unsaturated bond with polymerism etc. is for example arranged for example.
As above-mentioned optical polymerism compound (C), preferably has the multi-functional optical polymerism compound of the functional group more than 3.As this multi-functional optical polymerism compound tetramethylol methane tetraacrylate, pentaerythrite tetramethyl acrylate, dipentaerythritol five acrylate, dipentaerythritol pentamethyl acrylate, dipentaerythritol acrylate, dipentaerythritol hexamethyl acrylate etc. are arranged for example with the functional group more than 3.Above-mentioned optical polymerism compound (C) can use separately, also can make up more than 2 kinds and use, and its content is with respect to the solid constituent in the photosensitive composition, in massfraction, preferred 7～65 quality %, more preferably 13～60 quality %, further preferred 17～55 quality %.The content of above-mentioned optical polymerism compound (C) is in above-mentioned scope, has film thickness ratios before and after solidifying fully, developing to improve, undercutting (undercut) is difficult to enter pattern and adaptation becomes good tendency, and is therefore desirable.
Photosensitive composition of the present invention contains Photoepolymerizationinitiater initiater (D).As above-mentioned Photoepolymerizationinitiater initiater (D), there are acetophenone based compound, living radical to produce agent, acid producing agent etc. for example.
As above-mentioned acetophenone based compound, for example diethoxy acetophenone, 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) propane-1-ketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1-[4-(2-hydroxyl-oxethyl) phenyl are arranged for example] propane-1-ketone, 1-hydroxy-cyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] oligomer etc. of propane-1-ketone, preferred 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) propane-1-ketone etc.
Living radical produces agent and produces living radical by rayed.Produce agent as above-mentioned living radical benzoin based compound, benzophenone based compound, thioxanthones based compound, triazine based compound, oxime compound etc. are arranged for example.
As above-mentioned benzoin based compound benzoin, benzoin methyl ether, benzoin ethylether, benzoin isopropyl ether, benzoin isobutyl ether etc. are arranged for example.
As above-mentioned benzophenone based compound for example benzophenone, o-benzoyl benzoic acid methyl esters, 4-phenyl benzophenone, 4-benzoyl-4 '-methyldiphenyl base sulfide, 3 are arranged for example; 3 '; 4; 4 '-four (tert-butyl hydroperoxide carbonyl) benzophenone, 2; 4,6-tri-methyl benzophenone etc.
As above-mentioned thioxanthones based compound for example 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2 are arranged for example, 4-diethyl thioxanthone, 2,4-dichloro-thioxanthones, 1-chloro-4-propoxyl group thioxanthones etc.
Have 2 for example as above-mentioned triazine based compound, two (the trichloromethyl)-6-(4-methoxyphenyl)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl naphthyl)-1 of 4-, 3, the 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl-styrene)-1,3 of 4-, the 5-triazine, 2, two (trichloromethyl)-6-[2-(5-methylfuran-2-yl) vinyl of 4-]-1,3,5-triazines, 2, two (trichloromethyl)-6-[2-(furans-2-yl) vinyl of 4-]-1,3, the 5-triazine, 2, two (trichloromethyl)-6-[2-(4-diethylamino-2-aminomethyl phenyl) vinyl of 4-]-1,3, the 5-triazine, 2, two (trichloromethyl)-6-[2-(3, the 4-Dimethoxyphenyl) vinyl of 4-]-1,3,5-triazine etc.
As above-mentioned oxime compound for example O-acyl group oxime compound is arranged for example; its object lesson has 1-(4-phenyl sulphur aminoacyl phenyl)-butane-1 for example; 2-diketone-2-oxime O-benzoic ether; 1-(4-phenyl sulphur aminoacyl phenyl)-octane-1; 2-diketone-2-oxime-O-benzoic ether; 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl] ethyl ketone (エ タ ノ Application)-1-O-acetic acid esters; 1-[9-ethyl-6-(2-methyl-4-(3; 3-dimethyl-2,4-dioxo cyclopentyl (ペ Application タ ニ Le) methoxyl) benzoyl)-9H-carbazole-3-yl] ethyl ketone (エ タ ノ Application)-1-O-acetic acid esters etc.
Producing agent as the living radical beyond the above-mentioned illustration also can use as 2,4,6-trimethylbenzene formyl diphenyl phosphine oxide, 2,2 '-two (adjacent chlorophenyls)-4,4 ', 5,5 '-tetraphenyl-1,2 '-two imidazoles, 10-butyl-2-chloro acridone, 2-EAQ, dibenzoyl, 9,10-phenanthrenequione, camphorquinone, phenyl glyoxalic acid methylester, two cyclopentadiene titanium compounds etc.
As above-mentioned acid producing agent, salt or toluenesulfonic acid nitrobenzyl salt (or ester) class, toluenesulfonic acid benzoin salt (or ester) class etc. of 4-hydroxy phenyl dimethyl sulfonium tosilate, 4-hydroxy phenyl dimethyl sulfonium hexafluoro stibate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, 4-acetoxyl group phenyl methyl benzyl sulfonium hexafluoro stibate, triphenylsulfonium tosilate, triphenylsulfonium hexafluoro stibate, diphenyl iodine tosilate, diphenyl iodine hexafluoro stibate etc. are arranged for example.
In addition, produce the compound that generation living radical and acid are also arranged in the agent at above-mentioned living radical.For example, triazine is that Photoepolymerizationinitiater initiater also uses as acid producing agent.
The content of Photoepolymerizationinitiater initiater (D) is with respect to the total amount of adhesive resin (B) and optical polymerism compound (C), in massfraction, and preferred 0.1～30 quality %, more preferably 1～20 quality %.The content of Photoepolymerizationinitiater initiater is in above-mentioned scope, and high sensitivityization, time shutter shorten, and throughput rate improves, and is therefore desirable.
Can further contain photopolymerization in the photosensitive composition of the present invention and cause auxiliary agent (F).Photopolymerization causes auxiliary agent (F) makes up with Photoepolymerizationinitiater initiater (D) usually and uses, and is the polymeric compounds that is used to promote by the optical polymerism compound of polymerization initiator initiated polymerization.
Cause auxiliary agent (F) as photopolymerization amine compound, alkoxy anthracene based compound, thioxanthones based compound etc. are arranged for example.
As above-mentioned amine compound, for example triethanolamine is arranged for example, methyldiethanolamine, triisopropanolamine, 4-dimethylamino benzoic acid methyl esters, 4-dimethylamino ethyl benzoate, 4-dimethylamino benzoic acid isopentyl ester, benzoic acid-2-dimethylamino ethyl ester, 4-dimethylamino benzoic acid-2-Octyl Nitrite, N, the N-dimethyl-p-toluidine, 4,4 '-two (dimethylamino) benzophenone (common name Michler's keton), 4,4 '-two (diethylamino) benzophenone, 4,4 '-two (ethylmethylamino) benzophenone etc., wherein, 4,4 '-two (diethylamino) benzophenone is especially preferred.
As above-mentioned alkoxy anthracene based compound, for example have 9 for example, 10-dimethoxy anthracene, 2-ethyl-9,10-dimethoxy anthracene, 9,10-diethoxy anthracene, 2-ethyl-9,10-diethoxy anthracene, 9,10-dibutoxy anthracene, 2-ethyl-9,10-dibutoxy anthracene etc.
As above-mentioned thioxanthones based compound, for example 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2 are arranged for example, 4-diethyl thioxanthone, 2,4-dichloro-thioxanthones, 1-chloro-4-propoxyl group thioxanthones etc.
Photopolymerization causes auxiliary agent (F) can be used separately, also can make up more than 2 kinds and use.In addition, cause auxiliary agent (F) as photopolymerization and also can use commercially available product, commercially available photopolymerization causes auxiliary agent (F) for example trade name " EAB-F " (hodogaya chemical industry (strain) manufacturing) etc. for example.
Combination as Photoepolymerizationinitiater initiater in the photosensitive composition of the present invention (D) and photopolymerization initiation auxiliary agent (F), diethoxy acetophenone/4 are arranged for example, 4 '-two (diethylamino) benzophenone, 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) propane-1-ketone/4,4 '-two (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone/4,4 '-two (diethylamino) benzophenone, benzyl dimethyl ketal/4,4 '-two (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-[4-(2-hydroxyl-oxethyl) phenyl] propane-1-ketone/4,4 '-two (diethylamino) benzophenone, 1-hydroxycyclohexylphenylketone/4,4 '-two (diethylamino) benzophenone, 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] oligomer/4 of propane-1-ketone, 4 '-two (diethylamino) benzophenone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone/4,4 '-two (diethylamino) benzophenone etc., preferable examples has 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) propane-1-ketone/4,4 '-two (diethylamino) benzophenone.
When using these photopolymerization to cause auxiliary agent (F), with respect to per 1 mole of Photoepolymerizationinitiater initiater (D), preferred 0.01～10 mole of its use amount, more preferably 0.01～5 mole.
Photosensitive composition of the present invention contains solvent (E).As solvent (E), ethers, the ketone outside aromatic hydrocarbon based, above-mentioned, alcohols, ester class, amide-type, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO) etc. are arranged for example.
As above-mentioned ethers, tetrahydrofuran is arranged for example, oxinane, 1, the 4-dioxane, the glycol monomethyl methyl ether, ethylene glycol monomethyl ether, the glycol monomethyl propyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, the diethylene glycol single-butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, the diethylene glycol dipropyl ether, the diethylene glycol dibutyl ethers, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, propylene glycol list propyl ether acetic acid esters, methylcellosolve acetate, ethyl cellosolve acetate, the ethyl carbitol acetic acid esters, acetate of butyl carbitol, anisoyl, phenetol, methyl methoxy benzoyl etc.
As above-mentioned aromatic hydrocarbon based, for example benzene,toluene,xylene, mesitylene etc. are arranged for example.
As above-mentioned ketone, for example acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2 pentanone, 4-hydroxy-4-methyl-2 pentanone, cyclopentanone, cyclohexanone etc. are arranged for example.
As above-mentioned alcohols, for example methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol, glycerine etc. are arranged for example.
As above-mentioned ester class, for example ethyl acetate is arranged for example, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl isobutyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, hydroxy methyl acetate, hydroxyl ethyl acetate, the glycolic acid butyl ester, methoxy menthyl acetate, the methoxyacetic acid ethyl ester, the methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, the 3-hydroxy methyl propionate, 3-hydracrylic acid ethyl ester, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, the 2 hydroxy propanoic acid methyl esters, the 2 hydroxy propanoic acid ethyl ester, the 2 hydroxy propanoic acid propyl ester, 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-hydroxy-2-methyl methyl propionate, 2-hydroxy-2-methyl ethyl propionate, 2-methoxyl-2 Methylpropionic acid methyl esters, 2-ethoxy-2 Methylpropionic acid ethyl ester, methyl pyruvate, ethyl pyruvate, Propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, 2-ketobutyric acid methyl esters, 2-ketobutyric acid ethyl ester, acetate-3-methoxyl butyl ester, acetate-3-methyl-3-methoxyl butyl ester, gamma-butyrolacton etc.
As above-mentioned amide-type, for example N is arranged for example, dinethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone etc.
Wherein, preferred propylene glycol methyl ether acetate, propylene glycol monomethyl ether and 4-hydroxy-4-methyl-2 pentanone are with these and with then better.
Again, above-mentioned solvent can use separately, use more than 2 kinds also capable of being combined.
The content of the solvent in the photosensitive composition (E) is with respect to photosensitive composition, in massfraction, and preferred 70～95 quality %, more preferably 75～90 quality %.The content of solvent (E) is in above-mentioned scope, and the flatness when coating is arranged is good and colour saturation can be enough and display characteristic is good tendency when forming color filter, therefore ideal.
Photosensitive composition of the present invention also can further contain surfactant (G).Have for example as surfactant (G) that to be selected from polysiloxane series surfactant, fluorine be surfactant and the polysiloxane series surfactant with fluorine atom at least a kind.
As above-mentioned polysiloxane series surfactant, surfactant with siloxane bond etc. is arranged for example.Particularly, ト one レ polysiloxane DC3PA is arranged for example, same SH7PA, same DC11PA, same SH21PA, same SH28PA, same 29SHPA, same SH30PA, polyether modified silicon oil SH8400 (manufacturing of trade name: ト one レ polysiloxane (strain)), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (SHIN-ETSU HANTOTAI's polysiloxane is made), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufacturing of モ メ Application テ イ Block パ Off オ one マ Application ス マ テ リ ア Le ズ ジ ヤ パ Application contract company) etc.
As above-mentioned fluorine is surfactant, and surfactant with fluorocarbon chain etc. is arranged for example.Particularly, Off ロ ラ one De (trade name) FC430, same FC431 (manufacturing of Sumitomo ス リ one エ system (strain)), メ ガ Off ア Star Network (registered trademark) F142D, same F171, same F172, same F173, same F177, same F183, same R30 (DIC (strain) manufacturing), エ Off ト Star プ (trade name) EF301, same EF303, EF351, EF352 (new autumn fields changes into (strain) and makes), サ one Off ロ Application (trade name) S381, same S382, same SC101, same SC105 (Asahi Glass (strain) manufacturing), E5844 (manufacturing of (strain) ダ イ キ Application Off ア イ Application ケ ミ カ Le research institute), BM-1000, BM-1100 (all be trade name: BM Chemie company makes) etc.
As above-mentioned polysiloxane series surfactant, surfactant with siloxane bond and fluorocarbon chain etc. is arranged for example with fluorine atom.Particularly, メ ガ Off ア Star Network (registered trademark) R08, same BL20, same F475, same F477, same F443 (DIC (strain) manufacturing) etc.
These surfactants can use separately, use more than 2 kinds also capable of being combined.
The content of surfactant (G) is with respect to photosensitive composition, in massfraction, and preferred 0.00001～0.1 quality %, more preferably 0.00005～0.01 quality %.The content of surfactant (G) has the good tendency of flatness in above-mentioned scope, and is therefore desirable.
As using photosensitive composition of the present invention to form the method for patterning of color filter, following method is arranged for example and use the method etc. of the ink-jet machine need not photo-engraving process, said method is, photosensitive composition of the present invention (for example is coated on substrate or another resin bed, earlier at another photosensitive composition layer that forms on the substrate etc.) on, remove the volatile ingredient desolvate and to wait, form dyed layer, be situated between by photomask expose this dyed layer and development.
Can obtain high the filming of luminance brightness according to photosensitive composition of the present invention.
Embodiment
Below, illustrate in greater detail the present invention according to embodiment, but the present invention is not limited to these embodiment.The short of special record of " % " in the example and " part " is exactly weight % and weight portion.
Synthesis example 1
In flask, drop into 15 parts of sulphonyl rhodamines (ス Le ホ ロ one ダ ミ Application) B (Northeast chemistry is made), 150 parts of chloroforms and 9.8 parts of N with cooling tube and stirring apparatus, dinethylformamide, under agitation maintain below 20 ℃ on one side, Yi Bian drip 12.0 parts of thionyl chlorides.Dropping liquid is warming up to 50 ℃ after finishing, and keeps this temperature and makes it reaction in 5 hours, is cooled to 20 ℃ then.On one side cooled reaction solution is under agitation maintained below 20 ℃, on one side dropping liquid add the mixed liquor of 13.9 parts of 2 ethyl hexylamines and 24.5 parts of triethylamines.Then, made it reaction in 5 hours synthermal the stirring down.Then, distill the solvent of removing in the resulting reaction mixture, add small amount of methanol then, carry out high degree of agitation with rotary evaporator.While stirring this potpourri is added in the mixed liquor of 375 parts of ion exchange waters, crystallization is separated out.Filter out the crystallization of separating out, carefully clean,, obtain 14.7 parts of dyestuff A1 at 60 ℃ of following drying under reduced pressure with ion exchange water.
Figure G2009101584409D00251
Synthesis example 2
In flask, drop into the pigment shown in 15 parts of formula A0-2 (China and foreign countries change into manufacturing), 150 parts of chloroforms and 7.1 parts of N with cooling tube and stirring apparatus, dinethylformamide, Yi Bian under agitation maintain below 20 ℃, Yi Bian drip 8.7 parts of thionyl chlorides.Dropping liquid is warming up to 50 ℃ after finishing, and keeps this temperature and makes it reaction in 5 hours, is cooled to 20 ℃ then.On one side cooled reaction solution is under agitation maintained below 20 ℃, Yi Bian drip the mixed liquor of 10 parts of 2 ethyl hexylamines and 17.7 parts of triethylamines.Then, made it reaction in 5 hours synthermal the stirring down.Then, distill the solvent of removing in the resulting reaction mixture, add small amount of methanol then, carry out high degree of agitation with rotary evaporator.While stirring this potpourri is added in the mixed liquor of 375 parts of ion exchange waters, crystallization is separated out.Filter out the crystallization of separating out, carefully clean,, obtain 12.7 parts of dyestuff A2 (mixed dye of dyestuff A2-1～dyestuff A2-7) at 60 ℃ of following drying under reduced pressure with ion exchange water.
Figure G2009101584409D00261
(in the formula (A2), R d, R eAnd R fExpression-SO independently of one another 3 -,-SO 3Na or-SO 2NHR aR aExpression 2-ethylhexyl.)
Figure G2009101584409D00271
Synthesis example 3
In flask, drop into the pigment shown in 15 parts of formula A0-3 (China and foreign countries change into manufacturing), 150 parts of chloroforms and 8.9 parts of N with cooling tube and stirring apparatus, dinethylformamide, Yi Bian under agitation maintain below 20 ℃, Yi Bian drip 10.9 parts of thionyl chlorides.Dropping liquid is warming up to 50 ℃ after finishing, and keeps this temperature and makes it reaction in 5 hours, is cooled to 20 ℃ then.On one side cooled reaction solution is under agitation maintained below 20 ℃, Yi Bian drip the mixed liquor of 12.5 parts of 2 ethyl hexylamines and 22.1 parts of triethylamines.Then, made it reaction in 5 hours synthermal the stirring down.Then, distill the solvent of removing in the resulting reaction mixture, add small amount of methanol then, carry out high degree of agitation with rotary evaporator.While stirring this potpourri is added in the mixed liquor of 375 parts of ion exchange waters, crystallization is separated out.Filter out the crystallization of separating out, carefully clean,, obtain 11.3 parts of dyestuff A3 (mixed dye of dyestuff A3-1～dyestuff A3-8) at 60 ℃ of following drying under reduced pressure with ion exchange water.
Figure G2009101584409D00281
(in the formula (A3), R g, R hAnd R iRepresent independently of one another hydrogen atom ,-SO 3 -,-SO 3H or-SO 2NHR aR aExpression 2-ethylhexyl.)
Synthesis example 4
Has stirring machine, thermometer, the backflow cooling tube, in the flask of tap funnel and nitrogen ingress pipe, import the 182g propylene glycol monomethyl ether, atmosphere is become after the nitrogen by air, after being warming up to 100 ℃, splash into a kind of solution, continue down to stir at 100 ℃ again, this solution is by 70.5g (0.40 mole) benzyl methacrylate, (43.0g 0.5 mole) methacrylic acid, 22.0g added 3.6g 2 in the potpourri that monomethacrylates of (0.10 mole) tricyclodecane skeleton (Hitachi changes into (strain) system FA-513M) and 136g propylene glycol monomethyl ether constitute, 2 '-azobis isobutyronitrile forms.Then, atmosphere in the flask is become air by nitrogen, in flask, drop into 35.5g[0.25 mole, (carboxyl with respect to the methacrylic acid that is used for this reaction is 50 moles of %)] glycidyl methacrylate, 0.9g three (dimethylaminomethyl) phenol and 0.145g quinhydrones, continue reaction down at 110 ℃, obtaining the solid constituent acid number is the resin solution B1 of 79mgKOH/g.The weight-average molecular weight of the polystyrene conversion of being measured by GPC is 30,000.
Under following condition, carry out the mensuration of weight-average molecular weight of the polystyrene conversion of above-mentioned resin with the GPC method.
Device: HLC-8120GPC (TOSOH (strain) manufacturing)
(chromatogram) post: TSK-GELG2000HXL
(chromatogram) column temperature: 40 ℃
Solvent: THF
Flow velocity: 1.0mL/ branch
Detected liquid-solid body constituent concentration: 0.001～0.01 quality %
Injection rate IR: 50 μ L
Detecting device: RI
The calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500,
A-500 (TOSOH (strain) manufacturing)
Embodiment 1
[preparation of photosensitive composition 1]
Mix following material, use porose beaded glass grinding machine (PVC one ズ ミ Le) that pigment is disperseed fully,
(A) colorant C.I. pigment blue 15: 6 20 parts
5 parts of acrylic acid series pigment dispersing agents
137 parts of propylene glycol monomethyl ether
Then, mix following material, obtain photosensitive composition 1.
(A) colorant: 3.5 parts of dyestuff A1
(B) resin: 157 parts of resin solution B1
(C) optical polymerism compound: 50 parts of dipentaerythritol acrylates
(Japanese chemical drug (strain) manufacturing)
(D) 15 parts of Photoepolymerizationinitiater initiater: OXE-01
(manufacturing of チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ company)
(E) solvent: 289 parts of 4-hydroxy-4-methyl-2 pentanones
[formation of pattern]
Glass substrate (イ one グ Le 2000 2 inches of the length of sides; コ one ニ Application グ society makes] go up with after the spin-coating method coating photosensitive composition 1,100 ℃ of following preliminary dryings 3 minutes, after the cooling, make the 100 μ m that are spaced apart of substrate that is coated with this photosensitive composition and quartz glass system photomask, use exposure machine (TME-150RSK with pattern; ト プ コ Application (strain) is made), in air atmosphere, with 150mJ/cm 2Exposure (365nm benchmark) carry out rayed.After the rayed, with above-mentioned film under 23 ℃, to be immersed in contain in the water system developer solution that nonionic is surfactant 0.12% and potassium hydroxide 0.04% 80 seconds, develop, after the washing, in baking oven, carry out back baking 20 minutes under 220 ℃.Put cold after, use determining film thickness device (DEKTAK3; ULVAC Corp's manufacturing) thickness of the resulting cured pattern of mensuration is 2.2 μ m.
[evaluation]
For filming on the glass substrate that obtains, use colour examining machine (OSP-SP-200; Olympus (strain) is made) measure beam split, use illuminant-C measure xy chromaticity coordinate in the XYZ color specification system of CIE (Bx, By) and luminance brightness.The result represents at table 1.
Embodiment 2～5
Except dyestuff A1 is changed to the dyestuff shown in the table 1, other obtain photosensitive composition with embodiment 1 the samely and film.The result represents at table 1.
[table 1]
Embodiment 1 Embodiment 2 Embodiment 3 Embodiment 4 Embodiment 5
Dyestuff ????A1 ????A2 ????A3 ????A4 ※ ????A5 ※
????Bx ????0.141 ????0.138 ????0.141 ????0.141 ????0.141
????By ????0.085 ????0.085 ????0.085 ????0.085 ????0.085
Luminance brightness ????9.7 ????9.7 ????9.7 ????9.6 ????9.5
※ dyestuff A4: rhodamine B (ridge, field chemistry is made)
Figure G2009101584409D00311
※ dyestuff A5: rhodamine B base (ア Le De リ Star チ manufacturing)
Figure G2009101584409D00312
Confirm to use formed the filming of photosensitive composition of embodiment 1～5 to have high brightness.
Utilizability on the industry
According to the present invention, can obtain filming and colour filter of high brightness. Resulting colour filter is applicable to liquid crystal display cells or solid-state imager.

Claims (10)

1. photosensitive composition, contain colorant (A), adhesive resin (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D) and solvent (E), wherein, colorant (A) is to contain the organic solvent soluble dye of the compound that comprises formula (1) expression and the colorant of organic pigment
Figure A2009101584400002C1
In the formula (1), R 1～R 4Represent independently of one another hydrogen atom ,-R 6The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 6,-OH ,-OR 6,-SO 3 -,-SO 3H ,-SO 3M ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9Replace,
R 5Expression-SO 3 -,-SO 3H ,-SO 3M ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
M represents 0～5 integer, when m is a integer more than 2, and a plurality of R 5Can be the same or different,
X represents halogen atom, and a represents 0 or 1 integer,
R 6The saturated hydrocarbyl of expression carbon number 1～10, the contained hydrogen atom of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can be replaced by halogen atom, the contained methylene of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can by oxygen atom, carbonyl or-NR 6-replace,
R 8And R 9Represent the straight chain of carbon number 1～10 independently of one another or contain side chain alkyl, carbon number 3～30 naphthenic base or-Q, perhaps R 8And R 9Bonding and form the heterocycle of carbon number 1～10 mutually,
Q represents the aromatic hydrocarbyl of carbon number 6～10 or the aromatic heterocycle of carbon number 5～10, the contained hydrogen atom of above-mentioned aromatic hydrocarbyl and aromatic heterocycle can by-OH, R 6,-OR 6,-NO 2,-CH=CH 2,-CH=CHR 6Perhaps halogen atom replaces,
The straight chain of carbon number 1～10 or contain the alkyl of side chain and hydrogen atom that the naphthenic base of carbon number 3～30 is contained can by hydroxyl, halogen atom ,-Q ,-CH=CH 2Perhaps-CH=CHR 6Replace,
The straight chain of carbon number 1～10 or contain the alkyl of side chain and methylene that the naphthenic base of carbon number 3～30 is contained can by oxygen atom, carbonyl or-NR 6-replace,
The contained hydrogen atom of the heterocycle of carbon number 1～10 can be by R 6,-OH or-Q replaces,
M represents sodium atom or potassium atom.
2. photosensitive composition as claimed in claim 1, wherein, the compound of formula (1) expression is the compound of formula (1-1) expression,
Figure A2009101584400003C1
In the formula (1-1), R 11～R 14Represent independently of one another hydrogen atom ,-R 6The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 6,-OH ,-OR 6,-SO 3 -,-SO 3H ,-SO 3Na ,-CO 2H ,-CO 2R 6,-SO 3R 6,-SO 2NHR 8Perhaps-SO 2NR 8R 9Replace,
R 15The expression hydrogen atom ,-SO 3 -,-SO 3H ,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
R 16Expression-SO 3 -,-SO 3H ,-SO 2NHR 8Perhaps-SO 2NR 8R 9,
R 6, R 8, R 9, m, X and a represent meaning same as described above.
3. photosensitive composition as claimed in claim 1, wherein, the compound of formula (1) expression is the compound of formula (1-2) expression,
Figure A2009101584400003C2
In the formula (1-2), R 21～R 24Represent independently of one another hydrogen atom ,-R 26The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can by halogen atom ,-R 26,-OH ,-OR 26,-SO 3 -,-SO 3Na ,-CO 2H ,-CO 2R 26,-SO 3H ,-SO 3R 26Perhaps-SO 2NHR 28Replace,
R 25Expression-SO 3 -,-SO 3Na ,-CO 2H ,-CO 2R 26,-SO 3H or-SO 2NHR 28,
R 26The saturated hydrocarbyl of expression carbon number 1～10, the contained hydrogen atom of the saturated hydrocarbyl of above-mentioned carbon number 1～10 can be by-OR 26Perhaps halogen atom replaces,
R 28The expression hydrogen atom ,-R 26,-CO 2R 26The perhaps aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of the aromatic hydrocarbyl of above-mentioned carbon number 6～10 can be by-R 26Perhaps-OR 26Replace,
M, X and a represent meaning same as described above.
4. as each described photosensitive composition in the claim 1～3, wherein, the compound of formula (1) expression is the compound of formula (1-3) expression,
Figure A2009101584400004C1
In the formula (1-3), R 31And R 32Represent phenyl independently of one another, the contained hydrogen atom of above-mentioned phenyl can by halogen atom ,-R 26,-OR 26,-CO 2R 26,-SO 3R 26Perhaps-SO 2NHR 28Replace,
R 33Expression-SO 3 -Perhaps-SO 2NHR 28,
R 34The expression hydrogen atom ,-SO 3 -Perhaps-SO 2NHR 28,
R 26, R 28, X and a represent meaning same as described above.
5. as each described photosensitive composition in the claim 1～4, wherein, the compound of formula (1) expression is the compound of formula (1-4) expression,
In the formula (1-4), R 41And R 42Represent phenyl independently of one another, the contained hydrogen atom of above-mentioned phenyl can be by-R 26Perhaps-SO 2NHR 28Replace,
R 43Expression-SO 3 -Perhaps-SO 2NHR 28,
R 26, R 28, X and a represent meaning same as described above.
6. as each described photosensitive composition in the claim 1～5, wherein, organic pigment is for containing the C.I. pigment blue 15: 6 organic pigment.
7. photosensitive composition as claimed in claim 6, wherein, the C.I. pigment blue 15 in the colorant (A): 6 with the mass ratio of the organic solvent soluble dye of the compound that contains formula (1) expression be 97: 3～50: 50.
8. film for one kind, it uses each the described photosensitive composition in the claim 1～7 to form.
9. color filter, it uses each the described photosensitive composition in claim 1～7 to form.
10. color filter as claimed in claim 9, it forms by photo-engraving process.
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JPWO2022059619A1 (en) 2020-09-17 2022-03-24

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006010909A (en) * 2004-06-24 2006-01-12 Sumitomo Chemical Co Ltd Colored photosensitive composition
JP2006079012A (en) * 2004-09-13 2006-03-23 Mitsubishi Chemicals Corp Blue color filter and liquid crystal display using the same
CN101086619A (en) * 2006-06-08 2007-12-12 住友化学株式会社 Color photosensitive resin compositions

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11242109A (en) * 1998-02-25 1999-09-07 Toppan Printing Co Ltd Color composition for color filter and color filter using that
JP2001124915A (en) * 1999-10-26 2001-05-11 Toppan Printing Co Ltd Color composition for color filter, color filter and color liquid crystal display
JP2001290019A (en) * 2000-04-04 2001-10-19 Toppan Printing Co Ltd Color filter and liquid crystal display device equipped with the same
JP2002014221A (en) 2000-06-30 2002-01-18 Sumitomo Chem Co Ltd Color filter array having green filter layer and method for manufacturing the same
JP2005255753A (en) * 2004-03-10 2005-09-22 Mitsubishi Chemicals Corp Curable resin composition, color filter, and liquid crystal display
JP4717370B2 (en) * 2004-05-12 2011-07-06 富士フイルム株式会社 Color filter
JP2006008789A (en) * 2004-06-24 2006-01-12 Sumitomo Chemical Co Ltd Dyestuff, colored photosensitive composition containing the dyestuff, color filter using the colored photosensitive composition and image sensor equipped with the color filter
JP2006008586A (en) * 2004-06-25 2006-01-12 Toyo Ink Mfg Co Ltd Energy ray-sensitive acid-generating agent, method for generating acid, and energy ray-sensitive curable composition
JP2006017777A (en) * 2004-06-30 2006-01-19 Nippon Paint Co Ltd Manufacturing method of color filter, and liquid crystal display using the same
JP2006276512A (en) * 2005-03-29 2006-10-12 Fuji Photo Film Co Ltd Photosetting image recording material, and, color filter and method for manufacturing the same
JP2007316179A (en) * 2006-05-24 2007-12-06 Sumitomo Chemical Co Ltd Colored photosensitive resin composition for forming color filter to be provided in image sensor, color filter, image sensor and camera system

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006010909A (en) * 2004-06-24 2006-01-12 Sumitomo Chemical Co Ltd Colored photosensitive composition
JP2006079012A (en) * 2004-09-13 2006-03-23 Mitsubishi Chemicals Corp Blue color filter and liquid crystal display using the same
CN101086619A (en) * 2006-06-08 2007-12-12 住友化学株式会社 Color photosensitive resin compositions

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Publication number Priority date Publication date Assignee Title
JP2010211198A (en) * 2009-02-13 2010-09-24 Sumitomo Chemical Co Ltd Color photosensitive resin composition, color pattern and color filter
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CN102636956A (en) * 2011-02-09 2012-08-15 住友化学株式会社 Colored photosensitive resin composition
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CN103764767A (en) * 2011-08-30 2014-04-30 富士胶片株式会社 Novel compound having xanthene derivative multimeric structure, colored composition, ink for inkjet recording, inkjet recording method, color filter, and color toner
CN103034051A (en) * 2011-10-07 2013-04-10 住友化学株式会社 Colored curable resin composition
CN103176361A (en) * 2011-12-26 2013-06-26 住友化学株式会社 Colour cured resin composition
CN103176361B (en) * 2011-12-26 2018-06-29 住友化学株式会社 Colored curable resin composition
CN104011595A (en) * 2011-12-26 2014-08-27 第一毛织株式会社 Photosensitive resin composition for color filter and color filter using the same
CN104011595B (en) * 2011-12-26 2017-06-30 第一毛织株式会社 Photosensitive resin composition for colored filter and use its colored filter
CN103360790A (en) * 2012-04-10 2013-10-23 住友化学株式会社 Colorant Dispersion liquid
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