CN101604120A - Photosensitive composition - Google Patents
Photosensitive composition Download PDFInfo
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- CN101604120A CN101604120A CNA200910159562XA CN200910159562A CN101604120A CN 101604120 A CN101604120 A CN 101604120A CN A200910159562X A CNA200910159562X A CN A200910159562XA CN 200910159562 A CN200910159562 A CN 200910159562A CN 101604120 A CN101604120 A CN 101604120A
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- paratonere
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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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- 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
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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
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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
- G03F7/027—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
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Photosensitive composition, it comprises pigment (A), adhesive resin (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D) and solvent (E), and pigment (A) is the pigment that comprises C.I. paratonere 177, C.I. paratonere 242 and C.I. paratonere 254, in whole pigment, the content of C.I. paratonere 242 is below the 60 weight %.
Description
Technical field
The present invention relates to photosensitive composition.
Background technology
The color filter that uses in colour liquid crystal display device, the colour TV camera etc. normally forms the transparent painted fine pattern of red (R), green (G) and indigo plant 3 looks such as (B) and makes on opaque substrates such as transparency carrier such as glass or silicon.Transparent painted fine pattern comprises photosensitive composition, mixes colours according to the kind and the content of contained pigment in the photosensitive composition.
For example, disclose in patent documentation 1 and contained C.I. paratonere 177 and C.I. paratonere 242, in whole pigment, the content of C.I. paratonere 242 is the photosensitive composition of 65～90 weight %.
[patent documentation 1]: No. the 3924872nd, Japan's special permission
Summary of the invention
Can make the red pixel of high-contrast and the photosensitive composition of color filter is expected.
The present invention is a photosensitive composition, it comprises pigment (A), adhesive resin (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D) and solvent (E), and pigment (A) is the pigment that comprises C.I. paratonere 177, C.I. paratonere 242 and C.I. paratonere 254, in whole pigment, the content of C.I. paratonere 242 is below the 60 weight %.
In addition, above-mentioned photosensitive composition of the present invention, in whole pigment, the content of C.I. paratonere 242 is below the 50 weight %.
In addition, above-mentioned photosensitive composition of the present invention, in whole pigment, the content of C.I. paratonere 242 is below the 35 weight %.
In addition, above-mentioned photosensitive composition of the present invention, in whole pigment, the content of C.I. paratonere 254 is below the 80 weight %.
In addition, above-mentioned photosensitive composition of the present invention, in whole pigment, the content of C.I. paratonere 254 is below the 50 weight %.
In addition, the present invention is to use the pixel that above-mentioned photosensitive composition forms.
In addition, the present invention is the color filter that contains above-mentioned pixel.
Embodiment
Photosensitive composition of the present invention comprises pigment (A), adhesive resin (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D) and solvent (E), and pigment (A) is the pigment that comprises C.I. paratonere 177, C.I. paratonere 242 and C.I. paratonere 254, in whole pigment, the content of C.I. paratonere 242 is below the 60 weight %.
All the content of the C.I. paratonere 242 in the pigment is preferably below the 50 weight %, more preferably below the 35 weight %.In addition, also be preferably more than the 5 weight %, more preferably more than the 15 weight %.C.I. the content of paratonere 242 is so long as above-mentioned scope just can form the high red pixel of brightness and colour purity.
All the content of the C.I. paratonere 177 in the pigment is preferably more than the 5 weight %, more preferably more than the 10 weight %.In addition, also be preferably below the 95 weight %, more preferably below the 85 weight %.C.I. the content of paratonere 177 is so long as above-mentioned scope just can form the high red pixel of brightness and colour purity.
All the content of the C.I. paratonere 254 in the pigment is preferably below the 80 weight %, more preferably below the 50 weight %, more preferably below the 40 weight %.In addition, also be preferably more than the 5 weight %, more preferably more than the 20 weight %.C.I. the content of paratonere 254 is so long as above-mentioned scope, and the foreign matter that sweat goes out deposits yields will tail off.
In addition, pigment (A) also can contain any pigment as toner pigment.
As red pigment, can list C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,180,192,209,215,216,224,255,264,265 etc.These red pigments can be distinguished use separately, also can make up more than 2 kinds and use.
As blue pigment, can list the C.I. pigment blue 15: 3,15:4,76 etc., preferably can list the C.I. pigment blue 15: 3,15:4 and 76 more preferably can list the C.I. pigment blue 15: 3.These blue pigments can be distinguished use separately, also can make up more than 2 kinds and use.
As yellow uitramarine, C.I. pigment yellow 2,10,13,20,24,31,53,55,83,86,93,94,109,110,117,125,137,138,139,147,148,150,151,153,154,166,173,180 or 185 etc. can be listed, preferably C.I. pigment yellow 83,139,150 can be listed.These yellow uitramarines can be distinguished use separately, also can make up more than 2 kinds and use.
Further, as toning usefulness, can also in these pigment, add C.I. pigment green 36 or C.I. pigment Green 7.
The content of pigment (A) is benchmark with the solid state component total amount in the photosensitive composition, be generally more than the 10 weight %, below the 60 weight %, be preferably 10 weight % above, below the 55 weight %, more preferably 15 weight % above, below the 50 weight %.If the content of pigment (A) is above-mentioned scope, then the color depth when making color filter is abundant, and can contain the binder polymer of necessary amount in composition, therefore can form the sufficient pattern of physical strength.
Adhesive resin (B) preferably has alkali dissolution.In addition, adhesive resin (B) plays the effect of the dispersion medium of pigment (A).Aforementioned adhesion agent resin (B) is preferably the multipolymer that comprises derived from the structural unit of unsaturated carboxylic acid.
As aforementioned structural unit, can list the structural unit of derived from propylene acid particularly and derived from the structural unit of methacrylic acid derived from unsaturated carboxylic acid.Acrylic acid and methacrylic acid can be distinguished use separately, perhaps are used in combination 2.In addition, except these acrylic acid and methacrylic acid, can also and be selected from crotonic acid, itaconic acid, maleic acid, fumaric acid etc. other unsaturated carboxylic acid and at least a kind of carboxylic acid of unsaturated carboxylic acid anhydrides.In addition, can also be also with α-such monomer that in a part, contains hydroxyl and carboxyl of (methylol) acrylic acid.
Aforementioned adhesion agent resin (B) is preferably the multipolymer that comprises following structural unit, and this structural unit is to comprise above-mentioned structural unit derived from unsaturated carboxylic acid, and can with the structural unit of above-mentioned structural unit copolymerization derived from unsaturated carboxylic acid.As can with the structural unit of above-mentioned structural unit copolymerization derived from unsaturated carboxylic acid, preferably can list structural unit derived from (methyl) acrylate.
Can list acrylate compounds as (methyl) acrylate, particularly, can list the not replacement or the substituted alkyl ester of the such unsaturated carboxylic acid of (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) butyl acrylate, (methyl) acrylic acid benzyl ester, (methyl) acrylic acid 2-hydroxyethyl ester and (methyl) acrylic-amino ethyl ester;
(methyl) acrylic acid cyclopentyl ester, (methyl) acrylic acid cyclohexyl ester, (methyl) acrylic acid methylcyclohexyl ester, (methyl) acrylic acid suberyl ester, (methyl) acrylic acid ring octyl group ester, (methyl) acrylic acid
(menthyl) ester, (methyl) acrylic acid cyclopentenyl ester, (methyl) acrylic acid cyclohexenyl group ester, (methyl) acrylic acid cycloheptenyl ester, (methyl) acrylic acid cyclooctene base ester, (methyl) acrylic acid ` dialkylene ester, (methyl) isobornyl acrylate, (methyl) acrylic acid pinane base ester, (methyl) acrylic acid three ring decyl ester, (methyl) acrylic acid three ring oxygen base ethyl esters in the last of the ten Heavenly stems, (methyl) acrylic acid adamantane esters, (methyl) acrylic acid norborene ester, (methyl) acrylic acid pinane alkenyl esters, the ester that contains alicyclic group of the unsaturated carboxylic acid that (methyl) acrylic acid dicyclopentenyloxyethyl methacrylate and (methyl) acrylic acid dicyclo amylene oxygen base ethyl ester are such;
The unsaturated carboxylic acid glycidyl esters that (methyl) acrylic acid glycidyl esters is such;
The unsaturated carboxylic acid oxetane that (methyl) acrylic acid oxetane is such;
Single saturated carboxylic acid esters of the glycols that low polyalkylene glycol monoalkyl (methyl) acrylate is such etc. preferably can list (methyl) acrylic acid methyl, (methyl) acrylic acid benzyl ester.Here, (methyl) acrylate is represented acrylate or methacrylate.
Adhesive resin (B) can also further contain can with other structural unit of unsaturated carboxylic acid and acrylic ester copolymer.As can with other structural unit of unsaturated carboxylic acid and acrylic ester copolymer, can list the such aromatic ethenyl compound of styrene, α-Jia Jibenyixi and vinyltoluene;
The vinyl carboxylates that vinyl acetate and propionate are such;
The vinyl cyanide based compound that (methyl) vinyl cyanide and α-Lv Daibingxijing are such;
Derived from structural unit of the such imide compound of N-phenylmaleimide etc.
Above-mentioned these compounds can be distinguished use separately, also can make up more than 2 kinds and use.
As can with the structural unit derived from the structural unit copolymerization of unsaturated carboxylic acid, be preferably structural unit, especially preferably do not replace or substituted alkyl ester and (methyl) acrylic acid structural unit that contains the ester of alicyclic hydrocarbon radical derived from (methyl) is acrylic acid derived from (methyl) acrylate.
In adhesive resin (B), in the entire infrastructure unit of aforementioned multipolymer,, exist for 10～50 quality % usually derived from the structural unit of unsaturated carboxylic acid in mass fraction, be preferably 15～40 quality %.If the structural unit derived from unsaturated carboxylic acid is calculated as 10～50 quality % with aforementioned benchmark, then the dissolubility to developer solution is abundant, therefore can on the substrate of unexposed portion, not produce residue, and when developing, the film loss of the pixel portion of exposure portion does not take place, pixel integral body is not peeled off, so preferred.
Copolymerization uses polymerization initiator to carry out in solvent usually.As polymerization initiator, for example can list 2,2 '-azobis isobutyronitrile or 2, two (2 Methylpropionic acid methyl esters) the such azo-compounds of 2 '-azo.The superoxide that benzoyl peroxide or tert-butyl peroxide are such etc.In addition, solvent be so long as can dissolve getting final product of each monomer, can list such diol alcohol esters of ethylene glycol monomethyl ether acetate for example, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters etc.Temperature of reaction can consider that the decomposition temperature of polymerization initiator or the boiling point of solvent and monomer etc. decide.In addition, the side chain apparatus of the multipolymer that obtains like this there be the compound modified of photonasty group, also can form photosensitive adhesive resin (B).At this moment, can add the catalyzer that is used for introducing the photonasty group at resin.As catalyzer, can list for example three-dimethylaminomethyl phenol.In addition, can also add the adjuvant that is used to prevent subsidiary reaction.Can list for example quinhydrones as adjuvant.
The weight-average molecular weight of the polystyrene conversion of adhesive resin (B) is preferably 5,000～100, and 000, more preferably 7,000～50,000.If the weight-average molecular weight of polystyrene conversion adhesive resin (B)) is 5,000～100,000, be difficult to take place the film loss when then exist developing, and the good trend of removal of non-pixel portion when developing, so preferred.
Adhesive resin (B) contains 5～90 quality % usually with respect to the solid state component total amount in the photosensitive composition, is preferably 10～70 quality %.If the content of aforementioned adhesion agent resin (B) is counted 5～90 quality % with aforementioned benchmark, then exist the dissolubility of developer solution abundant, be difficult to produce the development residue on the substrate of non-pixel portion, and be difficult to take place the film loss of the pixel portion of exposure portion when developing, so the trend that the removal of non-pixel portion is good is preferred.
Contained optical polymerism compound (C) is to cause polymeric compounds by light and Photoepolymerizationinitiater initiater (D) in the photosensitive composition of the present invention, for example is the compound with carbon-to-carbon unsaturated bond.As aforementioned lights polymerizable compound (C), can list monofunctional monomer, 2 functional monomers, other polyfunctional monomer.
As the object lesson of monofunctional monomer, can list nonyl phenyl carbitol acrylate, 2-hydroxyl-3-phenoxy propyl acrylate, 2-ethylhexyl carbitol acrylate, acrylic acid 2-hydroxyethyl ester, N-vinyl pyrrolidone etc.
In addition, object lesson as 2 functional monomers, can list 1, two (acryloxy ethyl) ethers of 6-hexanediol two (methyl) acrylate, ethylene glycol bisthioglycolate (methyl) acrylate, neopentyl glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, bisphenol-A, 3-methyl pentanediol two (methyl) acrylate, tristane dimethanol two (methyl) acrylate etc.
As the object lesson of other polyfunctional monomer, can list trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, dipentaerythritol six (methyl) acrylate, three (methacryloxyethyl) chlorinated isocyanurates etc.
(C) especially preferably has acryloyl group (CH as the aforementioned lights polymerizable compound
2=CHCO-), and the many compounds of the acryloyl group quantity of the compound of per unit weight, just; gram numerical table with the compound of the acryloyl group of per 1 equivalent shows; the compound that the acryloyl group equivalent is few, wherein, preferred acryloyl group equivalent is the compound below 100.If acryloyl group when quantitative change big, then exposure or when developing, the susceptibility deficiency, the throughput rate that involves color filter sometimes reduces.As the acryloyl group equivalent is monomer below 100; glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, dipentaerythritol acrylate etc. can be listed, preferably trimethylolpropane triacrylate, tetramethylol methane tetraacrylate or dipentaerythritol acrylate etc. can be listed.In addition, as optical polymerism compound (C), preferred 2 functional monomers, other polyfunctional monomer.
The content of optical polymerism compound (C) with respect to add up in the photosensitive composition 100 mass parts adhesive resin (B) and optical polymerism compound (C), be generally 1～60 mass parts, be preferably 5～50 mass parts.If the content of optical polymerism compound (C) is aforementioned range, then there are the trend that becomes good in the intensity of pixel portions, pattern form or flatness, so preferred.
As optical polymerism initiating agent (D), can list by irradiates light and produce the living radical generation agent of living radical, acidic acid producing agent.Produce agent as living radical, can list for example acetophenones Photoepolymerizationinitiater initiater, styrax class Photoepolymerizationinitiater initiater, triazines Photoepolymerizationinitiater initiater, benzophenone Photoepolymerizationinitiater initiater and oximes Photoepolymerizationinitiater initiater etc.
As the acetophenones Photoepolymerizationinitiater initiater, can list for example 2-methyl-2-morpholino-1-(4-methyl thio-phenyl) third-1-ketone, diethoxy acetophenone, 2-hydroxy-2-methyl-1-phenyl third-1-ketone, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1-[4-(2-hydroxyl-oxethyl) phenyl] third-1-ketone, 1-hydroxycyclohexylphenylketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) fourth-1-ketone, 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl]-oligomer of third-1-ketone etc.
As styrax class Photoepolymerizationinitiater initiater, can list for example styrax, styrax methyl ether, styrax ethylether, benzoin isobutyl propyl group ether, benzoin isobutyl butyl ether etc.
As the triazines Photoepolymerizationinitiater initiater, for example can list 2, 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-piperonyls 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 the benzophenone Photoepolymerizationinitiater initiater; can list for example benzophenone, neighbour-benzoyl methyl benzoate, 4-phenyl benzophenone, 4-benzoyl-4 '-dimethyl diphenyl sulfide, 3; 3 '; 4; 4 '-four (tert-butyl hydroperoxide carbonyl) benzophenone, 2; 4,6-tri-methyl benzophenone etc.
As oxime compound; can list for example O-acyl group oxime compound; as its concrete example; can list 1-(4-phenyl sulfonyl phenyl)-Ding-1; 2-diketone 2-oxime-O-benzoic ether, 1-(4-phenyl sulfonyl-phenyl)-Xin-1; 2-diketone 2-oxime-O-benzoic ether, 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl] ethane 1-O-acetic acid esters, 1-[9-ethyl-6-(2-methyl-4-(3; 3-dimethyl-2,4-dioxane amyl group methyl oxygen base) benzoyl)-9H-carbazole-3-yl] ethane 1-O-acetic acid esters etc.
Produce agent as the living radical beyond the previous example; for example can list 2; 4; 6-trimethylbenzoyl diphenyl phosphine oxide, 2,2 '-two (neighbour-chlorophenyl)-4,4 '; 5; 5 '-tetraphenyl-1,2 '-bisglyoxaline, 10-butyl-2-chloro acridone, 2-EAQ, dibenzoyl, 9,10-phenanthrenequione, camphorquinone, phenyl glyoxalic acid methylester, two cyclopentadiene titanium compounds etc.
As acid producing agent, for example can list 4-hydroxy phenyl dimethyl sulfonium right-salt or nitrobenzyl toluenesulfonic acid salt, styrax toluenesulfonic acid salt etc. such as toluene sulfonate, 4-hydroxy phenyl dimethyl sulfonium antimony hexafluoride hydrochlorate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, 4-acetoxyl group phenyl-methyl-benzyl sulfonium hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium antimony hexafluoride hydrochlorate, diphenyl iodine tosilate, diphenyl iodine hexafluoro antimonate.
In addition, producing as living radical in the above-claimed cpd of agent, can be the compound that produces living radical and acid simultaneously, and for example, triazines Photoepolymerizationinitiater initiater isoreactivity free-radical generating agent also can be used as acid producing agent and uses.
These Photoepolymerizationinitiater initiaters (D) can be distinguished use separately, also can make up more than 2 kinds and use.
Photoepolymerizationinitiater initiater (D) also can the combined light polymerization cause the auxiliary agent use.Cause auxiliary agent as the aforementioned lights polymerization, preferred amines compound, the compound that contains mercapto and carboxylic acid compound, in addition, as more preferably aromatic amines compound of amines.
As amines, can list fatty amine compounds such as triethanolamine, methyldiethanolamine, triisopropanolamine; 4-dimethylaminobenzoic acid methyl esters, 4-dimethylaminobenzoic acid ethyl ester, 4-dimethylaminobenzoic acid isopentyl ester, 4-dimethylaminobenzoic acid 2-ethylhexyl, benzoic acid 2-dimethyl aminoethyl ester, N, N-dimethyl-p-toluidine, 4, aromatic amines compounds such as 4 '-two (dimethylamino) benzophenone (so-called michaelis ketone (Michler ' s ketone)), 4,4 '-two (diethylamino) benzophenone.
The compound that contains mercapto is the compound that has mercapto in molecule, as the mercaptan compound that contains 1 mercapto, can list 2-mercaptobenzothiazole, 2-mercaptobenzoxazole etc.; As the aliphatics multi-functional thiol's compound that in aliphatic group, has a plurality of mercaptos, can list ethanthiol, the last of the ten Heavenly stems two mercaptan, 1,4-dimethyl sulfydryl benzene, the two thiopropionates of butylene glycol, the two thiacetates of butylene glycol, ethylene glycol bis thiacetate, trimethylolpropane tris thiacetate, the two thiopropionates of butylene glycol, trimethylolpropane tris thiopropionate, trimethylolpropane tris thiacetate, pentaerythrite tetrathio propionic ester, pentaerythrite tetrathio acetic acid esters, trihydroxyethyl three sulfo-propionic esters etc.
As carboxylic acid compound, can list phenyl thioacetic acid, aminomethyl phenyl thioacetic acid, ethylphenyl thioacetic acid, Methylethyl phenyl thioacetic acid, 3,5-dimethylphenyl thioacetic acid, methoxyphenyl thioacetic acid, Dimethoxyphenyl thioacetic acid, chlorophenyl thioacetic acid, dichloro-phenyl thioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthyl thioacetic acid, N-naphthyl glycocoll, naphthoxy acetic acid.
In addition, except them, can also list the thioglycolic acid ester of multi-hydroxy compound and thiopropionate etc., as the thiopropionate of preferred multi-hydroxy compound, can list trimethylolpropane tris thiopropionate, trimethylolpropane tris thioglycolic acid ester and pentaerythrite tetrathio propionic ester.
With respect to total amount 100 mass parts of adhesive resin (B) and optical polymerism compound (C), the content of Photoepolymerizationinitiater initiater (D) is generally 0.1～40 mass parts, is preferably 1～30 mass parts.With respect to total amount 100 mass parts of adhesive resin (B) and optical polymerism compound (C), the content that photopolymerization causes auxiliary agent is generally 0.1～50 mass parts, is preferably 1～40 mass parts.
Solvent (E) can use all kinds of solvents that uses in this field.As its object lesson, can list the such ethylene glycol monoalkyl ether class of glycol monomethyl methyl ether, ethylene glycol monomethyl ether, glycol monomethyl propyl ether and ethylene glycol monobutyl ether;
The diglycol dialkyl ether that diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diglycol dipropyl ether and diglycol dibutyl ethers are such;
The ethylene glycol alkyl ether acetate esters that methylcellosolve acetate and ethyl cellosolve acetate are such;
Propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, propylene glycol list propyl ether acetic acid esters, methoxyl butylacetic acid ester and the such aklylene glycol alkyl ether acetate esters of methoxyl amyl group acetic acid esters;
Benzene,toluene,xylene, the such aromatic hydrocarbons of sym-trimethyl benzene;
The ketone that MEK, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone are such;
The such alcohols of ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol and glycerine;
The ester class that 3-ethoxyl ethyl propionate and 3-methoxypropionic acid methyl esters are such;
The cyclic ester class that gamma-butyrolacton is such etc.
These solvents (E) can be distinguished use separately, also can make up more than 2 kinds and use.
With respect to photosensitive composition integral body, the content of solvent (E) is generally 60～90 quality % in mass fraction, is preferably 70～85 quality %.If the content of aforementioned solvents (E) is aforementioned range, so the trend that then exists coating to become good is preferred.
In photosensitive composition of the present invention, can further contain adjuvants (F) such as filling agent, pigment dispersing agent, adhesion promoter, antioxidant, ultraviolet light absorber, anti-cohesion material, surfactant, other macromolecular compound.
As filling agent, can list glass, silica, aluminium oxide etc. particularly.
As pigment dispersing agent, can use commercially available pigment dispersing agent, for example can list surfactants such as silicone, fluorine class, ester class, cationic, anionic species, nonionic class, both sexes etc., can distinguish separately and use, also can make up more than 2 kinds and use.Example as aforementioned surfactants, can list the polyoxyethylene alkyl ether class, the polyoxyethylene alkyl phenyl ether class, the polyethylene glycol di class, the sorbitan aliphatic ester class, fatty acid modified polyesters, the tertiary amine modified polyurethane, polyethyleneimine: amine etc., and commodity KP (Shin-Etsu Chemial Co., Ltd's manufacturing) by name, Port リ Off ロ one (manufacturing of common prosperity KCC), エ Off ト Star プ (manufacturing of ト one ケ system プ ロ ダ Network Star company), メ ガ Off ア Star Network ス (Dainippon Ink. ﹠ Chemicals Inc's manufacturing), Off ロ ラ one ト (manufacturing of Sumitomo 3M Co., Ltd.), ア サ ヒ ガ one De, サ one Off ロ Application (more than, Asahi Glass Co., Ltd makes), ソ Le ス パ one ス (manufacturing of ア ピ シ ア Co., Ltd.), EFKA (manufacturing of EFKA CHEMICALS company), PB821 (manufacturing of monosodium glutamate Co., Ltd.) etc.
As adhesion promoter, can list vinyltrimethoxy silane particularly, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330, the 3-aminopropyltriethoxywerene werene, the 3-glycidoxypropyltrimewasxysilane, 3-glycidoxypropyl methyl dimethoxysilane, 2-(3, the 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloro propyl group methyl dimethoxysilane, the 3-chloropropyltrimethoxy silane, the 3-methacryloxypropyl trimethoxy silane, 3-sulfydryl propyl trimethoxy silicane etc.
As antioxidant, can list 2 particularly, 2 '-thiobis (4-methyl-6-tert butyl phenol), 2,6 di tert butyl 4 methyl phenol etc.
As ultraviolet light absorber, can list 2-(the 3-tert-butyl group-2-hydroxy-5-methyl base phenyl)-5-chlorinated benzotriazole, alkoxy benzophenone etc. particularly.
In addition, as anti-polycoagulant, can list sodium polyacrylate etc. particularly.
As surfactant, preferably has the surfactant of fluorine atom or silicon atom.Particularly, can list in the silicone surfactant that is selected from silicone surfactant, fluorine class surfactant and has fluorine atom at least a kind.
As the aforementioned silicone surfactant, can list surfactant with siloxane bond etc.Can list ト one レ シ リ コ one Application DC3PA particularly, ト one レ シ リ コ one Application SH7PA, ト one レ シ リ コ one Application DC11PA, ト one レ シ リ コ one Application SH21PA, ト one レ シ リ コ one Application SH28PA, ト one レ シ リ コ one Application 29SHPA, ト one レ シ リ コ one Application SH30PA, polyether modified silicon oil SH8400 (trade name, ト one レ シ リ コ one Application Co., Ltd. makes), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (Silicone of SHIN-ETSU HANTOTAI manufacturing), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufacturing of モ メ Application チ イ Block パ Off オ one マ Application ス マ テ リ ア Le ズ ジ ヤ パ Application affiliated company) etc.
As aforementioned fluorine class surfactant, can list and have surfactant of fluoridizing carbochain etc.Particularly, can list Off ロ ラ one De (trade name) FC430, Off ロ ラ one De FC431 (manufacturing of Sumitomo 3M Co., Ltd.), メ ガ Off ア Star Network (trade name) F142D, メ ガ Off ア Star Network F171, メ ガ Off ア Star Network F172, メ ガ Off ア Star Network F173, メ ガ Off ア Star Network F177, メ ガ Off ア Star Network F183, メ ガ Off ア Star Network F489, メ ガ Off ア Star Network F554, メ ガ Off ア Star Network R30 (Dainippon Ink Chemicals's manufacturing), エ Off ト Star プ (trade name) EF301, エ Off ト Star プ EF303, エ Off ト Star プ EF351, エ Off ト Star プ EF352 (new autumn fields changes into Co., Ltd. and makes), サ-Off ロ Application (trade name) S381, サ one Off ロ S382, サ one Off ロ SC101, サ one Off ロ SC105 (Asahi Glass Co., Ltd's manufacturing), E5844 (ダ イ キ Application Off ア イ Application ケ ミ カ Le research institute (Co., Ltd.) manufacturing), BM-1000, BM-1100 (all be trade name, BMChemie company makes) etc.
As aforementioned silicone surfactant, can list the surfactant etc. that has siloxane bond and fluoridize carbochain with fluorine atom.Particularly, can list メ ガ Off ア Star Network (login trade mark) R08, メ ガ Off ア Star Network BL20, メ ガ Off ア Star Network F475, メ ガ Off ア Star Network F477, メ ガ Off ア Star Network F443 (Dainippon Ink Chemicals's manufacturing) etc.
These surfactants can use separately, also can make up more than 2 kinds and use.
As other macromolecular compound, can use thermoplastic resins such as heat-curing resin, polyester, polyurethane, polyvinyl alcohol (PVA), polyacrylic acid, polyalkylene glycol monoalkyl ether, polyacrylic acid fluoroalkyl esters etc. such as epoxy resin particularly.
Photosensitive composition of the present invention for example can be prepared as follows.Just, with pigment (A) in advance and solvent (E) mix, use dispersions such as ball mill, be degree below the 0.2 μ m up to the mean grain size of pigment.At this moment, also use pigment dispersing agent as required sometimes, cooperate the adhesive resin (B) of part or all again.In the dispersion liquid (grinding matrix) of gained, add remaining adhesive resin (B), optical polymerism compound (C) and Photoepolymerizationinitiater initiater (D), as required, add employed other composition, and the solvent that appends as required, to reach the concentration of regulation, obtain the photosensitive composition of target.
Zhi Bei photosensitive composition can for example followingly be applied on the base material like this, carries out photocuring and development, makes colored pixels.At first, said composition is spun on the substrate (normally glass),, removes and desolvate, obtain level and smooth filming by carrying out heat drying (prebake).The coating thickness of this moment is approximately the degree of 1～3 μ m.Obtain like this film on be situated between by negative mask irradiation ultraviolet radiation to form target image.At this moment, preferably use devices such as mask steady arm,, and mask and substrate are overlapped in correct position so that parallel rays shines in exposure portion on the whole equably.And then, make filming after solidify finishing be contacted with dilute alkaline aqueous solution afterwards again, make the dissolving of non-exposure portion, develop, obtain target image thus.After the development, as required, can also under 150～230 ℃, carry out 10～60 minutes back curing (afterwards curing).
The developer solution that uses during development behind the pattern exposure normally contains the aqueous solution of alkali compounds and surfactant.
As alkali compounds, can list inorganic and organic alkali compounds.As the object lesson of inorganic alkaline compound, can list NaOH, potassium hydroxide, sodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate (ADP), potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, sal tartari, sodium bicarbonate, saleratus, sodium borate, potassium borate, ammonia etc.
In addition, as the object lesson of organic basic compound, can list tetramethyl ammonium hydroxide, hydroxide 2-hydroxyethyl trimethyl ammonium, monomethyl amine, dimethyl amine, Trimethylamine, single ethylamine, diethylamide, triethylamine, single isopropylamine, diisopropylamine, monoethanolamine etc.These inorganic and organic basic compounds can be distinguished separately and use, and also can make up more than 2 kinds and use.The preferred concentration of the alkali compounds in the alkaline developer is 0.01～10 quality %, more preferably 0.03～5 quality %.
In addition, the surfactant in the alkaline developer can list nonionic surfactant, anionic surfactant or cationic surfactant.
As nonionic surfactant, can list polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkylaryl ether, other polyoxyethylene deriv, ethylene oxide/propylene oxide segmented copolymer, sorbitan aliphatic ester, polyoxyethylene sorbitan aliphatic ester, polyoxyethylene sorbitol fatty acid ester, fatty acid glyceride, polyoxyethylene fatty acid ester, polyoxyethylene alkyl amine etc.
As anionic surfactant's object lesson, can list the such alkyl aryl sulfonate class of lauryl alcohol sodium sulfovinate or oleyl alcohol sodium sulfovinate such higher alcohol sulfate salt, NaLS or Texapon Special such alkylsurfuric acid salt, neopelex or dodecyl sodium naphthalene sulfonate etc.
As the object lesson of cationic surfactant, can list such amine salt of octadecyl amine hydrochlorate or Trimethyllaurylammonium chloride or quaternary ammonium salt etc.
These surfactants can be distinguished use separately, also can make up more than 2 kinds and use.
Surfactant concentrations in the alkaline developer, normally 0.01～10 quality % is preferably 0.05～8 quality %, more preferably 0.1～5 quality %.
Through the coating of photosensitive composition, drying, to the pattern exposure of gained dry coating, each operation that development afterwards is such, can obtain being equivalent to the color pixel of the coloring components in the photosensitive composition, then, repeat these operations of the quantity of the necessary color of color filter, can obtain color filter.Just, color filter can dispose red, green and blue three primary colors pixel usually on substrate.
Use photosensitive composition of the present invention to form red pixel.X in the preferred XYZ chromaticity diagram of this red pixel, y coordinate values are 0.500＜x＜0.690,0.280＜y＜0.340, more preferably 0.520＜x＜0.680,0.290＜y＜0.340.
According to the present invention, can make the red pixel and the color filter of high-contrast.
Contain the color filter that uses the pixel that photosensitive composition of the present invention obtains, can be suitable for various display device, for example liquid crystal indicator such as monitor or television etc.
Embodiment
Below, by embodiment the present invention is described more specifically." % " in the example and " part " are if there is no particular limitation then be weight % and weight portion.
Synthesizing of＜adhesive resin (B1) 〉
In the flask of the 1L that possesses stirrer, thermometer, reflux condensing tube, tap funnel and wireway, import the 133g propylene glycol monomethyl ether.Then, nitrogen is imported in the flask, make the atmosphere gas in the flask be replaced as nitrogen by wireway.Afterwards, solution in the flask is warmed up to 100 ℃, use tap funnel, through 2 hours, to comprise 2 of 22.0g (0.10mol) methacrylic acid dicyclo pentyl ester (FA-513M, Hitachi Chemical Co., Ltd. make), 82.8g (0.47mol) methacrylic acid benzyl ester, 37.0g (0.43mol) methacrylic acid, 3.6g, the potpourri of 2 '-azobis isobutyronitrile and 164g propylene glycol monomethyl ether is added drop-wise in the flask, after dripping, stirred 5 hours down at 100 ℃ again.
After stirring end, pass through wireway, air is imported in the flask, behind the atmosphere gas in the air displacement flask, 21.5g (0.15mol) glycidyl methacrylate, 0.9g three-dimethylaminomethyl phenol and 0.145g quinhydrones are dropped in the flask, continue reaction 6 hours down at 110 ℃, obtain the adhesive resin (B1) of solid state component 37.8 quality %, acid number 97mgKOH/g.
Here, acid number is in measuring and 1g carboxylic acid etc. has the value of amount (mg) of the necessary potassium hydroxide of polymkeric substance of acidic group, usually, tries to achieve by the potassium hydroxide aqueous solution titration that working concentration is known.
The adhesive resin of gained (B1) is 9,000 by the weight-average molecular weight of the polystyrene conversion that the GPC method of following condition is measured.
Device: HLC-8120GPC (eastern ソ one Co., Ltd. make)
Post: TSK-GELG2000HXL
Column temperature: 40 ℃
Solvent: THF
Flow velocity: 1.0mL/min
The solid component concentration of tested liquid: 0.001～0.01 quality %
Injection rate IR: 50 μ L
Detecting device: RI
Proofread and correct and use standard substance: TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500 (eastern ソ one Co., Ltd. manufacturing)
Other composition that uses in the present embodiment is as shown in table 1.
[table 1]
| Pigment | (A1) | C.I. paratonere 177 |
| (A2) | C.I. paratonere 242 | |
| (A3) | C.I. paratonere 254 | |
| The optical polymerism compound | (C) | Dipentaerythritol acrylate |
| Photoepolymerizationinitiater initiater | (D1) | OXE-01 (oxime compound, チ バ ス ペ シ ヤ Le テ イ ケ ミ カ Le ズ Co., Ltd. makes) |
| (D2) | 2, two (the trichloromethyl)-6-piperonyl-1,3,5-triazines of 4-, | |
| (D3) | 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) fourth-1-ketone | |
| Solvent | (E1) | Propylene glycol monomethyl ether |
| (E2) | Propylene glycol monomethyl ether | |
| (E3) | The 3-ethoxyl ethyl propionate | |
| Surfactant | (F) | メ ガ Off ア Star Network F475 (big Japanese ink (イ Application キ) chemical industry Co., Ltd. makes) |
(embodiment 1)
Mix each composition and form, obtain photosensitive composition 1 to become shown in the table 2.Use the photosensitive composition 1 of gained, estimate by the following method and film.
＜estimate with the manufacturing of filming
It is dry that 2 inches square glass substrates (manufacturing of #1737: コ one ニ Application グ company) are cleaned the back with neutral lotion, water and alcohol successively.
On this glass substrate, by spin-coating method coating photosensitive composition 1, then in the cleaning baking oven, 100 ℃ of following prebake 3 minutes.
After the cooling, use exposure machine (TME-150RSK; ト プ コ Application Co., Ltd. makes), under atmosphere, with 150mJ/cm
2Exposure (365nm) carry out rayed, 220 ℃ of down heating 20 minutes, make and estimate with filming.
The evaluation of＜film 〉
Use film thickness gauge (DEKTAK, Veeco company makes), evaluation of measuring uses micro-spectral light measurer (OSP-SP200, OLYMPUS company makes) with the thickness of filming, and measures colourity (x, y) and brightness (Y).In addition, using contrast analyzer (CT-1, kettle slope motor company makes), is 10000 with blank value, measures contrast value.The result is as shown in table 3.
[table 2]
(unit: %)
[table 3]
| Thickness (μ m) | x | ?y | ?Y | Contrast | ||
| Embodiment 1 | Composition 1 | ?2.40 | 0.658 | ?0.335 | ?20.0 | 3875 |
(embodiment 2～6)
According to the composition shown in the table 4 and embodiment 1 similarly, obtain photosensitive composition.Similarly estimate with embodiment 1, the result is as shown in table 5.
[table 4]
(unit: %)
[table 5]
| Thickness (μ m) | ?x | ?y | ?Y | Contrast | ||
| Embodiment 2 | Composition 2 | ?2.58 | ?0.658 | ?0.326 | ?18.3 | ?5574 |
| Embodiment 3 | Composition 3 | ?2.54 | ?0.658 | ?0.326 | ?18.4 | ?5027 |
| Embodiment 4 | Composition 4 | ?2.50 | ?0.658 | ?0.337 | ?20.5 | ?3727 |
| Embodiment 5 | Composition 5 | ?2.39 | ?0.658 | ?0.337 | ?20.4 | ?4293 |
| Embodiment 6 | Composition 6 | ?2.49 | ?0.658 | ?0.339 | ?20.5 | ?4936 |
Industrial applicability
According to the present invention, can make the red pixel and the color filter of high-contrast.
Claims (7)
1, photosensitive composition, it comprises pigment (A), adhesive resin (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D) and solvent (E), and pigment (A) is the pigment that comprises C.I. paratonere 177, C.I. paratonere 242 and C.I. paratonere 254, in whole pigment, the content of C.I. paratonere 242 is below the 60 weight %.
2, the described photosensitive composition of claim 1, in whole pigment, the content of C.I. paratonere 242 is below the 50 weight %.
3, the described photosensitive composition of claim 1, in whole pigment, the content of C.I. paratonere 242 is below the 35 weight %.
4, each described photosensitive composition in the claim 1～3, in whole pigment, the content of C.I. paratonere 254 is below the 80 weight %.
5, the photosensitive composition described in the claim 1～4, in whole pigment, the content of C.I. paratonere 254 is below the 50 weight %.
6, pixel, it uses, and each described photosensitive composition forms in the claim 1～5.
7, color filter, it contains the described pixel of claim 6.
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| JP2008-132911 | 2008-05-21 | ||
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| JP (1) | JP2010002886A (en) |
| KR (1) | KR20090121217A (en) |
| CN (1) | CN101604120B (en) |
| TW (1) | TW201003147A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106918992A (en) * | 2015-09-24 | 2017-07-04 | 东友精细化工有限公司 | Green photonasty resin composition, the colour filter comprising it and display device |
| CN110045578A (en) * | 2018-01-16 | 2019-07-23 | 东友精细化工有限公司 | Negative light-sensitive resin combination, photocuring film and image display device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5402158B2 (en) * | 2008-06-06 | 2014-01-29 | Ｊｓｒ株式会社 | Color composition for forming red pixel, color filter, and color liquid crystal display element |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100256392B1 (en) * | 1996-09-30 | 2000-05-15 | 겐지 아이다 | Photosensitive resin coloring composition for color filter, color filter formed therefrom, new anthraquinone compound and preparing method thereof |
| JP4428880B2 (en) * | 2001-04-11 | 2010-03-10 | 富士フイルム株式会社 | Coloring composition and photosensitive coloring composition |
| JP2002372618A (en) * | 2001-06-14 | 2002-12-26 | Fujifilm Arch Co Ltd | Red hardening composition for color filter and color filter using the same |
| TWI344976B (en) * | 2003-10-27 | 2011-07-11 | Sumitomo Chemical Co | Stained sensitization resin |
| JP4407410B2 (en) * | 2004-07-15 | 2010-02-03 | Ｊｓｒ株式会社 | Radiation sensitive composition for color filter and preparation method thereof |
| JP2006047686A (en) * | 2004-08-04 | 2006-02-16 | Jsr Corp | Radiation-sensitive composition for color filter, its preparation method, color filter and color liquid crystal display |
| JP2006220790A (en) * | 2005-02-09 | 2006-08-24 | Taiyo Ink Mfg Ltd | Photosensitive resin composition for display panel, its hardened material, and spacer for display panel |
| WO2007142293A1 (en) * | 2006-06-08 | 2007-12-13 | Sakata Inx Corp. | Red coloring composition for color filter |
-
2009
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106918992A (en) * | 2015-09-24 | 2017-07-04 | 东友精细化工有限公司 | Green photonasty resin composition, the colour filter comprising it and display device |
| CN106918992B (en) * | 2015-09-24 | 2021-04-06 | 东友精细化工有限公司 | Green photosensitive resin composition, color filter comprising same, and display device |
| CN110045578A (en) * | 2018-01-16 | 2019-07-23 | 东友精细化工有限公司 | Negative light-sensitive resin combination, photocuring film and image display device |
Also Published As
| Publication number | Publication date |
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| JP2010002886A (en) | 2010-01-07 |
| TW201003147A (en) | 2010-01-16 |
| CN101604120B (en) | 2016-01-20 |
| KR20090121217A (en) | 2009-11-25 |
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