CN100535748C - Red photoresist combination of color light filter used for LCD device and its application - Google Patents
Red photoresist combination of color light filter used for LCD device and its application Download PDFInfo
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- CN100535748C CN100535748C CNB2006101441365A CN200610144136A CN100535748C CN 100535748 C CN100535748 C CN 100535748C CN B2006101441365 A CNB2006101441365 A CN B2006101441365A CN 200610144136 A CN200610144136 A CN 200610144136A CN 100535748 C CN100535748 C CN 100535748C
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Abstract
The invention discloses a red optical impedance compositions that comprise red colourant, optically active polymer, optical activity monomer, dissolvent, optical initiating agent, disperser and additive. The optically active polymer is the photoconductor in the red optical impedance compositions that comprises mercaptan-polyene oligomers, it possesses two mechanisms of free radical polymerization and cationic polymerization, so the polymerization speed of optical impedance compositions is quick in exposure, the property of antioxidant polymerization is good and it possesses perfect image repeatability, analysis capability and high penetration. The applications of the red optical impedance compositions are: the red optical impedance compositions is applied to clean base plate via rotating, the red filter with high colour purity is formed via desiccation, exposure to ultraviolet light, development and baking, the colour filter and liquid crystal display are obtained by conventional producing method.
Description
Technical field
The present invention relates to the pigment photoresistor composition of color light filter used for LCD device, particularly the red photoresistance composition of color light filter used for LCD device.
Background technology
Along with popularizing rapidly of color liquid crystal display arrangement, the requirement that display color is shown improves constantly.General color liquid crystal display arrangement comprises that colored filter substrate and thin film transistor (TFT) (TFT) substrate are opposed and the gap portion of 1-10 μ m is set, at this gap portion filling liquid crystal material, with the structure of encapsulants such as epoxy resin with its periphery sealing.
The structure of colored filter is as follows: form successively on transparent glass substrate: 1) the black matrix in order to prevent that light from leaking; 2) realize the colored red green blue tricolor that shows; 3) diaphragm (this technology can be selected), its effect are the protection pixel portions and make the level and smooth effect of optical filter.
Inboard at colored filter substrate and thin film transistor base plate is provided with alignment films, and spacer is scattered here and there in inside, opposed gap.Then, by the light transmission rate of control liquid crystal layer and each pixel of colored filter, the final colour that obtains shows.
The propenoic acid ester photocureable system that the pigment photoresistor that traditional colored filter is used is contained; because its radical polymerization mechanism is subjected to the oxygen inhibition effect obvious; in polymerization process, often require inertia protection atmosphere such as nitrogen; or oxygen is set cuts off film; make complex technical process, increase extra cost and requirement.
Summary of the invention
The object of the invention is to provide a kind of light sensitivity height, and polymerization speed is fast, the red photoresistance composition that anti-oxygen inhibition is good.The present invention is by the improvement to conventional acrylic ester photocuring system, adopt the composite polymeric mechanism of free radical polymerization, cationic polymerization coexistence, the photosensitivity of photoresistance composition is strengthened, polymerization speed is accelerated, antioxygen resistance cumulative power improves, in exposure process, not needing to obtain the chromatic photoresist composition of special processing measure, thereby eliminate the inhibition of oxygen polymerization process.
To achieve these goals, the invention provides a kind of red photoresistance composition, comprise following component:
Weight percentages of components
Red 5%～55%
Optical active polymer 10%～40%
Photoactive monomer 5%～55%
Solvent 5%～55%
Light trigger 0.5%～15%
Spreading agent 0.5%～15%
Adjuvant 0%～5%
Described optical active polymer is: the compound that produces free radical polymerization and cationic polymerization, described optical active polymer is specially: the potpourri of polythiol and polyene oligomer, and with the composition of urethane acrylate, (methyl) acryl resin, methacrylic resin and cinnamic multipolymer, bisphenol-a epoxy acrylate or polyorganosiloxane resin.
In above-mentioned red photoresistance composition, the preferred weight percent of its each component is: the percentage by weight of described red is 15%～35%; The percentage by weight of described optical active polymer is 15%～25%; The percentage by weight of described photoactive monomer is 20%～35%; The percentage by weight of described solvent is 10%～25%; The percentage by weight of described light trigger is 2%～8%; The percentage by weight of described spreading agent is 2%～10%.
Described red is one of them or two or more combination of red pigment, yellow uitramarine or orange pigment.
The compound of described generation free radical polymerization and cationic polymerization comprises the potpourri of polythiol and polyene oligomer; Polythiol is one of them or two or more combination of trithioglycerin, tri-thiol methylpropane, tripropylene glycol two-(3-mercaptopropionic acid ester), pentaerythrite four-(3-mercaptopropionic acid ester), trimethylolpropane tris-(3-mercaptopropionic acid ester) and glycerine three-(3-mercaptopropionic acid ester) in the potpourri of described polythiol and polyene oligomer; The polyene oligomer is isocyanuric acid triallyl ester, trimethylolpropane tris allyl ether and C in the potpourri of polythiol and polyene oligomer
1～C
4Alkyl norborene formic ether one of them or two or more combination.
Described photoactive monomer contains vinyl ethers compound.
Described light trigger is one of them or two or more combination of acetophenone system, acylphosphine oxide, fragrant ketone, aromatic sulfonium salts, salt compounded of iodine and luxuriant molysite.
The present invention also provides a kind of colored filter, wherein comprises above-mentioned red photoresistance composition.
The present invention also provides a kind of LCD, wherein comprises above-mentioned colored filter.
The application of red as mentioned above photoresistance composition, the method that wherein red photoresistance composition is mixed by rotary coating, printing or ink-jet is coated on the clean substrate; Then with the substrate that coats 70～100 ℃ of dryings 5～10 minutes; Use ultraviolet photoetching again, illumination is 100～250mJ/cm
2, the coating after the exposure was soaked in imaging liquid 1～3 minute, and imaging liquid is NaOH or sodium carbonate liquor; In 200～250 ℃ of bakers, toasted 60～80 minutes at last, can obtain the pixel graphics of wanting.
The present invention is by the improvement to conventional acrylic ester photocuring system, adopt polythiol and polyene oligomer potpourri and with the composition of other composition, make the coexistence of its free radical polymerization and cationic polymerization, fully improved should redness photoresistance composition the antioxygen ability to cure, reduced simultaneously since pigment to the absorption of ultraviolet light and to the influence of light sensitivity.
Embodiment
Core content of the present invention is to have adopted two kinds of flowcollector aggregation scheme FlowCollectors and two kinds of light-initiated mechanism respectively.Below be described in detail.
Red used in the present invention is the potpourri of a kind of red pigment or multiple red pigment, or the composition of red pigment and other pigment, or the composition of other pigment, as yellow uitramarine, orange pigment.This red account for this redness photoresistance composition quality 5～55%, be preferably 15～35%.
The red pigment that can enumerate is based on perylene system, quinacridone and pyrrolopyrrole class: as P.R.122, and P.R.123, P.R.177, P.R.179, P.R.190, P.R.202, P.R.210, P.R.224, P.R.254, P.R.255, P.R.264, P.R.270, P.R.272, P.R.122.
Yellow uitramarine such as azo-type, azo condensed type and heterocyclic: P.Y.1, P.Y.12, P.Y.3, P.Y.13, P.Y.83, P.Y.93, P.Y.94, P.Y.95, P.Y.109, P.Y.126, P.Y.127, P.Y.138, P.Y.139, P.Y.139, P.Y.147, P.Y.150, P.Y.174, P.Y.180.
Orange pigment such as azo class, pyrazolone, diphenyl amine pigment: P.O.5, P.O.13, P.O.16, P.O.34, P.O.36, P.O.48, P.O.49, P.O.71, P.O.73.
Optical active polymer used in the present invention is the compound that free radical polymerization and cationic polymerization can take place, and is specifically as follows: the composition of the potpourri of polythiol and polyene oligomer and urethane acrylate, (methyl) acryl resin, methacrylic resin and cinnamic multipolymer, bisphenol-a epoxy acrylate or polyorganosiloxane resin.This optical active polymer content be this redness photoresistance composition quality 10～40%, content is lower than 10% and may occurs solidifying not exclusively, crosslinked back rete compactness is poor; Be higher than 40% and may cause the viscosity of photoresistance composition excessive, be unsuitable for follow-up rotary coating operation, and might influence the analysis feature of photoresistance composition.Content is preferably 15～25%.
Wherein polythiol is the sulfydryl acid esters of chain-like alkyl polythiol, polyvalent alcohol, other polynary sulfhydryl compounds, preferred trithioglycerin, tri-thiol methylpropane, tripropylene glycol two-(3-mercaptopropionic acid ester), pentaerythrite four-(3-mercaptopropionic acid ester), trimethylolpropane tris-(3-mercaptopropionic acid ester) and glycerine three-(3-mercaptopropionic acid ester) one of them or two or more combination.
Wherein the polyene oligomer is big molecular olefine or the polyolefin (structure (1)) that contains at least two above carbon-carbon double bonds, or contains the oligomer of allyl ether, ester structure, or the acrylate of polyene.The polybutadiene of the concrete alkane derivatives (structure (2)) that polybutadiene, norborene formic ether arranged for example, natural rubber, isocyanuric acid triallyl ester, trimethylolpropane tris allyl ether, ethoxylated trimethylolpropane triallyl ether, propoxylation trimethylolpropane tris allyl ether, acroleic acid esterification etc.Being preferably isocyanuric acid triallyl ester, trimethylolpropane tris allyl ether, R is the alkyl norborene formic ether of C1～C4.These oligomer may be used alone, can also be two or more kinds in combination.
Wherein polyorganosiloxane resin (structure (3)) has the polysiloxane of carbon-carbon double bond, can be crosslinked with many sulfydryls, and form the crosslinking curing film, thereby improve the photoresponse speed and the antioxygen resistance cumulative power of curing system, improve the tack of photocuring system to glass substrate.
Optical active polymer used in the present invention also can comprise urethane acrylate, and this polyurethane can be polyester polyol and isocyanate polymer, or polyethers and isocyanate polymer, or polysiloxane and isocyanate polymer.
Optical active polymer used in the present invention also can comprise (methyl) acryl resin or methacrylic resin and cinnamic multipolymer or bisphenol-a epoxy acrylate.
Photoactive monomer used in the present invention is for containing vinyl ethers compound, as contains CH
2The monomer of=CH-O-structure or (methyl) acrylic ester monomer.This photoactive monomer content be this redness photoresistance composition quality 5～55%, be preferably 20～35%.
Wherein contain CH
2The monomer dilution property of=CH-O-structure is good, the viscosity that can effectively regulate curing system, and can participate in cationic polymerization, effectively improve the antioxygen polymerization inhibition performance of photocuring system, thereby give photocuring system higher light sensitivity.Hydroxy butyl vinyl ether, triethylene glycol divinyl ether, 1 are arranged for example, 4-cyclohexyl dimethanol divinyl ether, butyl vinyl ether.
Photoactive monomer used in the present invention can also be (methyl) acrylic ester monomer.Wherein (methyl) acrylic ester monomer divides simple function group, difunctional, polyfunctional group again and contains methoxy end group (methyl) acrylic ester monomer.
Simple function group (methyl) acrylic ester monomer has n-butyl acrylate, isobutyl acrylate, senecioate-hydroxyl ethyl ester, methacrylic acid-beta-hydroxy ethyl ester, iso-bornyl acrylate, the beta-hydroxyethyl acrylate, lauryl acrylate, the lauryl methyl acrylate, different certain herbaceous plants with big flowers base acrylate, the tridecyl acrylate, the octadecyl acrylate, the docosyl acrylate, the stearic acid methacrylate, the 2-phenoxyethyl acrylate, isooctyl acrylate, the tetrahydrofurfuryl methacrylate.
Difunctional (methyl) acrylic ester monomer has 1, two (methyl) acrylate, two of 6-hexanediol contract propylene glycol double methacrylate, tripropylene glycol double methacrylate, two (methyl) acrylate of tirethylene glycol, two (methyl) acrylate of triethylene Glycol, tetraethoxy modified bisphenol A double methacrylate, eight ethoxy modified bisphenol A double methacrylates, two (methyl) acrylate of polyglycol, neopentyl glycol dipropoxy double methacrylate.
Polyfunctional group (methyl) acrylic ester monomer has trimethylolpropane tris (methyl) acrylate, pentaerythritol triacrylate, three-(2-hydroxyethyl) isocyanates triacrylate, tetramethylol methane tetraacrylate, dipentaerythrityl ether five acrylate, dipentaerythrityl ether six acrylate, two contract trimethylolpropane tetra-acrylate, ethoxylated trimethylolpropane triacrylate, propoxylated glycerol triacrylate.
Contain methoxy end group (methyl) acrylic ester monomer methoxy poly (ethylene glycol) (350) monomethacrylates, methoxy poly (ethylene glycol) (350) mono acrylic ester, methoxy poly (ethylene glycol) (550) monomethacrylates, methoxy poly (ethylene glycol) (550) mono acrylic ester are arranged.
Above-mentioned photoactive monomer may be used alone, can also be two or more kinds in combination.Be preferably hydroxy butyl vinyl ether, or hydroxy butyl vinyl ether and tetramethylol methane tetraacrylate composition, or hydroxy butyl vinyl ether, tetramethylol methane tetraacrylate and methoxy poly (ethylene glycol) (550) monomethacrylates composition one of them or two or more combination.
Solvent used in the present invention be this redness photoresistance composition quality 5～55%, be preferably 10～25%.The macromolecular compound that organic pigment is dispersed in the different performance type connects in the material, in the presence of solvent, will show specific colorability, glossiness, flowability and flocculating properties, these characteristics are not only relevant with molecular structure, the particle state of pigment, and are also relevant with solvent.Should select the polarity The suitable solvent according to the characteristics of pigment itself during the screening solvent.
The solvent that can select for use has acid flux material as formic acid, acetate, chloroform etc.; Basic solvent is as ketone, ester, ether, some aromatic hydrocarbon etc.; Neutral flux is as aliphatic hydrocarbon, cycloalkane compound and some aromatic hydrocarbon etc.Specifically have for example: fatty alcohol, glycol ether, ethyl acetate, MEK, methyl isobutyl ketone, monomethyl ether glycol ester, gamma-butyrolacton, butyl carbitol, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexane, dimethylbenzene, isopropyl alcohol.Wherein be preferably propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexane, butyl carbitol, butyl carbitol acetate and gamma-butyrolacton one of them or two or more combination.
The used light trigger of the present invention can be selected radical photoinitiator or cationic photoinitiator or the two combination for use.Photoinitiator levels is the 0.5%-15% of this redness photoresistance composition quality, is preferably 2%-8%.
Radical photoinitiator such as acetophenone series initiators, acylphosphine oxide, sulfur-bearing acetophenone are to contain morpholine tertiary amine base and thioether group in the photoinitiator molecules, have the collaborative effect that causes with the compound use of thioxanthone; Carry the Hydrogen initiating agent---as fragrant ketone, benzophenone and derivant thereof are arranged for example, methyl o-benzoylbenzoate, thioxanthone etc.;
Cationic photoinitiator such as aromatic sulfonium salts and salt compounded of iodine, luxuriant molysite class are as triphenyl sulfosalt, diaryl group iodized salt, the luxuriant iron saline oxide of η 6-isopropyl benzene, the luxuriant iron saline oxide of η 6-pyrene etc.
Above-mentioned light trigger may be used alone, can also be two or more kinds in combination.Be preferably acylphosphine oxide, two dodecyl benzene salt compounded of iodine, benzoin ether, 1-hydroxy-cyclohexyl acetophenone, acroleic acid esterification benzophenone, 4-dimethylamino ethyl benzoate, styrax dimethyl ether, sulphur band phenyl-to oxygen azo-cycle acetone and two methyl ammonia-to oxygen azo-cycle butanone one of them or two or more combination.
The used dispersant of the present invention is 0.5～15% of a red photoresistance composition quality, is preferably 2～10%.Effects such as that spreading agent plays in pigment photoresistor is wetting, dispersion, deflocculation and stable dispersion, reduction viscosity.Consider influences such as film formation time, film fastness, glossiness.The selected spreading agent of the present invention is acylamide polymer or modification polyurethane polymkeric substance, or contain the high-molecular block copolymer of close pigment group, or polyether-modified dimethyl polysiloxane multipolymer, or organic silicon surfactant, or modified polyurethane, or choose one or two or more combination in the modified polyacrylate.Commodity are by name: TA-100, DISPER BYK160,161,163,166,170,300,335,331,2150 series; EFKA46,47,452 series, EFKA Polymer400,403,64 series.
The used adjuvant of the present invention is in order to obtain more excellent performance, and its content accounts for the 0-5% of this redness photoresistance composition quality.Can use as required, as: activator, adhesion promoter, antioxidant, ultraviolet light absorber, anti flocculant etc.As in order to promote the effect of ultraviolet light polymerization, can add a spot of activator as required, commonly used in coloured system to the dialkylamino benzoic ether, as (dimethylamino)-ethyl benzoate and the different monooctyl ester of p-(dimethylamino)-benzoic acid, they cooperate with BP (benzophenone) or ITX (2-isopropyl thioxanthone), not only solidification rate can be improved greatly, O can also be removed effectively
2Thereby minimizing overcomes O
2Inhibition; Polymerization taking place when depositing for minimizing, improve the storage stability of resin, can select stabilizing agent for use, as p-dihydroxy-benzene, the methoxyl p-cresol, 1,4-benzoquinone, p-tert-butyl catechol, 2, the 5-di-tert-butyl hydroquinone, 2,5-is to a kind of or two or more combinations in the dimethyl 1,4-benzoquinone.
Above-mentioned each constituent preparation is evenly promptly got red photoresistance composition of the present invention, for example color compositions can be dispersed in earlier in the solvent that is added with spreading agent and form dispersible pigment dispersion, with optical active polymer, photoactive monomer, light trigger, spreading agent, and other auxiliary agents dissolvings, mix, again two groups of potpourris are mixed.
According to above embodiment, enumerate following examples, embodiment is illustrated, but does not constitute restriction implementing.
Embodiment 1:
The storage stability of the red photoresistance composition of gained is good, and video picture is good, and thermotolerance is good.
Embodiment 2:
The storage stability of the red photoresistance composition of gained is good, and video picture is good, good heat resistance.
Embodiment 3:
The storage stability of the red photoresistance composition of gained is good, and video picture is good, good heat resistance.
Embodiment 4:
The storage stability of the red photoresistance composition of gained is good, and video picture is good, and thermotolerance is good.
The application of red photoresistance composition described in the present invention, embodiment is as follows,
Embodiment 1:
Above-mentioned red photoresistance composition is coated on the clean substrate by the rotary coating mode of rotating speed at 400rpm～2000rpm, and substrate can be glass, macromolecular material, pottery, metal etc.; Then with the substrate that coats 70～100 ℃ of dryings 5～10 minutes; Use ultraviolet photoetching again, illumination is 100～250mJ/cm2, and the coating after the exposure was soaked in imaging liquid 1～3 minute, and imaging liquid is NaOH or sodium carbonate liquor; In 200～250 ℃ of bakers, toasted 60～80 minutes at last, can obtain the pixel graphics of wanting.
Green photoresistance, blue photoresistance are repeated said process, adopt conventional method can obtain described colored filter again.
Utilize above-mentioned colored filter to adopt conventional method for making, can obtain described LCD.
It should be noted last that, above embodiment is the unrestricted technical scheme of the present invention in order to explanation only, although the present invention is had been described in detail with reference to the foregoing description, will be understood by those skilled in the art that: still can make amendment or be equal to replacement the present invention, and do not break away from any modification or partial replacement of the spirit and scope of the present invention, all should contain within the scope of the invention.
Claims (9)
1, a kind of red photoresistance composition is characterized in that comprising following component:
Weight percentages of components
Red 5%～55%
Optical active polymer 10%～40%
Photoactive monomer 5%～55%
Solvent 5%～55%
Light trigger 0.5%～15%
Spreading agent 0.5%～15%
Adjuvant 0%～5%
Described optical active polymer is: the compound that produces free radical polymerization and cationic polymerization, described optical active polymer is specially: the potpourri of polythiol and polyene oligomer, and with the composition of urethane acrylate, (methyl) acryl resin, methacrylic resin and cinnamic multipolymer, bisphenol-a epoxy acrylate or polyorganosiloxane resin.
2, according to the described red photoresistance composition of claim 1, the percentage by weight of wherein said red is 15%～35%; The percentage by weight of described optical active polymer is 15%～25%; The percentage by weight of described photoactive monomer is 20%～35%; The percentage by weight of described solvent is 10%～25%; The percentage by weight of described light trigger is 2%～8%; The percentage by weight of described spreading agent is 2%～10%.
3, according to the described red photoresistance composition of claim 1, the compound of wherein said generation free radical polymerization and cationic polymerization comprises the potpourri of polythiol and polyene oligomer; Polythiol is one of them or two or more combination of trithioglycerin, tri-thiol methylpropane, tripropylene glycol two-(3-mercaptopropionic acid ester), pentaerythrite four-(3-mercaptopropionic acid ester), trimethylolpropane tris-(3-mercaptopropionic acid ester) and glycerine three-(3-mercaptopropionic acid ester) in the potpourri of described polythiol and polyene oligomer; The polyene oligomer is isocyanuric acid triallyl ester, trimethylolpropane tris allyl ether and C in the potpourri of described polythiol and polyene oligomer
1～C
4Alkyl norborene formic ether one of them or two or more combination.
4, according to claim 1 or 2 described red photoresistance compositions, wherein said red is one of them or two or more combination of red pigment, yellow uitramarine or orange pigment.
5, according to claim 1 or 2 described red photoresistance compositions, wherein said photoactive monomer contains vinyl ethers compound.
6, according to claim 1 or 2 described red photoresistance compositions, wherein said light trigger is one of them or two or more combination of acetophenone system, acylphosphine oxide, fragrant ketone, aromatic sulfonium salts, salt compounded of iodine and luxuriant molysite.
7, a kind of colored filter wherein comprises each described red photoresistance composition of claim 1 to 6.
8, a kind of LCD wherein comprises and utilizes the described colored filter of claim 7.
9, the application of each described red photoresistance composition of a kind of claim 1 to 6, the method that wherein red photoresistance composition is mixed by rotary coating, printing or ink-jet is coated on the clean substrate; Then with the substrate that coats 70～100 ℃ of dryings 5～10 minutes; Use ultraviolet photoetching again, illumination is 100～250mJ/cm
2, the coating after the exposure was soaked in imaging liquid 1～3 minute, and imaging liquid is NaOH or sodium carbonate liquor; In 200～250 ℃ of bakers, toasted 60～80 minutes at last, can obtain the pixel graphics of wanting.
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| CN101162364B (en) * | 2007-11-30 | 2011-04-20 | 京东方科技集团股份有限公司 | Photosensitive resin composition and method of making the same and film build method |
| CN101625525B (en) * | 2008-07-11 | 2013-06-12 | 住友化学株式会社 | Light-sensitive resin composition |
| JP5581614B2 (en) * | 2008-07-31 | 2014-09-03 | Ｊｓｒ株式会社 | Radiation-sensitive composition for forming colored layer, color filter, and color liquid crystal display element |
| CN101750887B (en) * | 2008-12-19 | 2012-07-18 | 京东方科技集团股份有限公司 | Photosensitive resin composition |
| KR101682937B1 (en) * | 2009-04-01 | 2016-12-06 | 제이에스알 가부시끼가이샤 | Radiation-sensitive resin composition, interlayer insulating film and method for forming the same |
| CN102650827B (en) * | 2011-06-08 | 2017-07-04 | 京东方科技集团股份有限公司 | Photosensitve resin composition and apply its liquid crystal display |
| CN111373325B (en) * | 2017-11-21 | 2023-10-17 | 东丽株式会社 | Silicone resin composition, cured film, and display device |
| CN109585502B (en) * | 2018-10-25 | 2020-09-08 | 深圳市华星光电技术有限公司 | Substrate for ink-jet printing and manufacturing method thereof |
| CN111077732A (en) * | 2019-12-20 | 2020-04-28 | 深圳市华星光电半导体显示技术有限公司 | Material composition of light coupling-out lens and manufacturing method thereof |
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