CN102627770A - Organosiloxane polymer, preparation method of the organosiloxane polymer, color photoresist for color filter, color filter and preparation method of the color filter - Google Patents
Organosiloxane polymer, preparation method of the organosiloxane polymer, color photoresist for color filter, color filter and preparation method of the color filter Download PDFInfo
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- CN102627770A CN102627770A CN2012100709343A CN201210070934A CN102627770A CN 102627770 A CN102627770 A CN 102627770A CN 2012100709343 A CN2012100709343 A CN 2012100709343A CN 201210070934 A CN201210070934 A CN 201210070934A CN 102627770 A CN102627770 A CN 102627770A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 51
- 229920000642 polymer Polymers 0.000 title claims abstract description 25
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 39
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
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- 125000000217 alkyl group Chemical group 0.000 claims description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 6
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
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- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 claims description 2
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- 239000010977 jade Substances 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 238000011085 pressure filtration Methods 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Images
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Abstract
The invention relates to an organosiloxane polymer, a preparation method of the organosiloxane polymer, a color photoresist containing the organosiloxane polymer, a color filter adopting the color photoresist and a preparation method of the color filter. The organosiloxane polymer can replace a levelling agent and a coupling agent in a color photoresist formula, and is superior to the traditional levelling agent or the coupling agent in the respect of a degree of polarity matching with other resins and solvents. An intramolecular pressure difference delta-F formed between double interfaces of a coated color film of the color photoresist and a substrate is controllable. The color photoresist realizes control of colloid shrinkage and forms a uniform coating having small shrinkage. The color photoresist realizes flatting of a coated color film, and good adhesiveness of pixel units and align markers on the color filter. A sample obtained by the preparation method of the color filter realizes excellent color uniformity, has high precision and prevents uneven compression of a liquid crystal display panel.
Description
Technical field
The present invention is specifically related to a kind of organo-siloxane high molecular polymer and preparation method thereof and the colored Photoresist that contains this polymkeric substance, and with the colored filter of colored Photoresist making and the preparation method of this colored filter.
Background technology
Colored filter can create through following process: with scattered redness (R) pigment, green (G) pigment and the agent of blueness (B) pigment photoresistor are coated on and form color film on the glass substrate that has black matrix; Vacuum and preceding baking; Ultraviolet photoetching under mask plate; Develop and make figure and back baking post bake.The film uniformity of final gained print should be controlled in 3% (the adopting 9 method tests); If homogeneity surpasses certain numerical value, it is inconsistent on liquid crystal panel, can to produce not bright spot or overall color homogeneity in the future, as: Japanese Patent, the spy opens flat 2003-337424 and puts down in writing.Require the print edge can not have the retraction of photoresist residual simultaneously, residual if the edge has, when the panel paster is made, can be because the irregular crowded broken substrate of pressurized.The solution of the problems referred to above can realize through the adjustment manufacture craft on the one hand; Can realize through adjustment photoresist prescription on the other hand.Normally technology and material all will have mutual cooperation.
In recent years, though flat be coated with (Slit) mode in large-sized glass substrate make colored filter and become mainstream technology, the relatively poor shortcoming of coating also is accompanied by all the time, especially when the color film of the above thickness of coating 2um.Thereby Japanese Patent JP155265/2006 discloses in order to improve the method that the problems referred to above obtain smooth uniform color film, and in Chinese patent CN101081942A, CN1991584A, discloses the flowability of using fluorine carbon functional group flow agent to strengthen photoresist.
But the use of flow agent is to select then according to integral material, as: solvent, the actual solubility parameter area of resin and special auxiliary agent matees thereby reach with colloidal dispersion.Though fluorine carbon flow agent has extremely strong reduction surface tension and increases the mobile effect of colloid; But for viscosity number at 5mpa*s with interior photoresist, do not need to reduce simply the flowability that surface tension increases color film; But need to consider color film and air, and the intramolecularly pressure difference Δ F between the double-deck interface that color film and substrate form (pressure reduction in being called for short), promptly IT is poor.When having only Δ F less than certain value, could control the colloid retraction, the color film that is coated on the glass substrate can form evenly and the little coating that bounces back.
In addition, the chromatic photoresist agent is when making color film, except avoiding smooth inadequately formed edge retraction; Be also noted that color film another interface problem to glass substrate---stick the adherence problem.Even have the color film of good interface Tension Difference, the situation that pixel lines (Pixel) come off also can appear behind exposure imaging sometimes; Be that pixel (Pixel) lines can adherence more sometimes, but trickleer figure, as: contraposition paster mark (Marker) comes off easily.Make that making liquid crystal panel goes wrong.
In order to address this is that, among U.S. Pat 4934791 and the US5863678 with base plate glass in the high different siloxanes coupling agent of silicon (Si) avidity.But,, often can make color film flatness descend again if coupling agent is improper with not enough coupling of system polarity or usage quantity.
Summary of the invention
The present invention proposes in view of the above problems.The objective of the invention is to through a kind of organo-siloxane high molecular polymer is provided; Make it in the chromatic photoresist agent, substitute traditional flow agent and coupling agent simultaneously and afterwards can also produce levelling and coupling performance; And the IT that can effectively control the colored filter volume is poor, thereby realizes color film planarization.
Another object of the present invention is to provide a kind of preparation method of said organo-siloxane high molecular polymer.
Another object of the present invention is to the colored Photoresist that provides a kind of colored filter of using said organo-siloxane high molecular polymer to use.
Another purpose of the present invention is to be provided in the colored filter that the said colored Photoresist of a kind of usefulness is made.
A purpose more of the present invention is to provide above-mentioned color filter making method.
For realizing above-mentioned purpose, the technical scheme that the present invention adopted is following:
A kind of organosiloxane polymer has the high molecular polymer of the structural unit of formula (1) expression:
General formula (1)
In the said general formula (1), X representes the Ar base, and Y representes the Ar base; R
1Expression straight chain or graft copolymer; R
2The expression alkylene, contain the N alkyl, contain a kind of in O alkyl or the halogen atom alkyl; R
3Expression hydrogen or methyl; R
4Expression methyl or ethyl; The n value is 5～300.
In the preferred scheme, the structure that X of the present invention representes is selected from C
6～C
30Ar base, Y representes C
6～C
30Ar base, wherein X and Y can be same base group, also can be different groups.The C more preferred, that described X representes
6～C
18Phenyl, a kind of in alkyl phenyl or the alkoxyl phenyl, Y representes C
6～C
18Phenyl, a kind of in alkyl phenyl or the alkoxyl phenyl.Wherein X or Y can specifically represent a kind of in the aryl such as phenyl, aminomethyl phenyl, 3,5-dimethylphenyl, trimethylphenyl, ethylphenyl, isopropyl phenyl, butyl phenyl, hydroxy phenyl, p-methoxy-phenyl, acetoxyl group phenyl, butoxy phenyl, chlorophenyl, bromo phenyl, dichloro-phenyl, chloromethyl phenyl, but X of the present invention, Y do not limit above-mentioned group.General formula (5) and general formula (6) are preferably from the compound of following structure:
As preferably, R of the present invention
1Expression C
2～C
30Saturated straight chain or graft copolymer.Wherein more preferred, said R
1Expression C
2～C
16Alkyl, polyester based, a kind of in alkyl, polyether base or the polyester polyether-based.R
1The compound of base will consider that at first the integral polarity of polymkeric substance and lower viscosity require (3-6mpa*s) scope when selecting; Secondly, consider color film and air, the intramolecularly pressure difference Δ F between the double-deck interface that color film and substrate form is as far as possible little; Realize that Photoresist has good wettability to glass substrate, represent good flowability, the homogeneity of color film is lower than 3%; Preferably, R
1Can specifically be selected from polyester based, alkyl gathers silica-based, polyether-based, alkyl, polyether base, the modification of many hydroxyls and gathers that silica-based, many hydroxyls are polyether-modified to be gathered silica-based, polyester modification and gather a kind of in silica-based, polyester polyether-based, propenoate polyester based, fluorine polyester based, perfluoroalkyl polyether base, hydroxyl telechelic polyester base, end hydroxy polyether base, epoxy group(ing) modified poly ester base, epoxy group(ing) modified polyether base, both-end base epoxy group(ing) modified polyether base, both-end base epoxy group(ing) modified poly ester base etc.; Preferred R
1Be selected from Mn (number-average molecular weight) for that polyester based, the alkyl of 1000-50000 scope gathers is silica-based, polyester modification gathers silica-based, propenoate polyester based, a kind of in the fluorine polyester based, epoxy group(ing) modified poly ester base, both-end base epoxy group(ing) modified poly ester based prepolymers etc.But R of the present invention
1Be not limited to above-mentioned group.
As preferably, R of the present invention
2Expression C
2～C
16Vinyl, aminoalkyl group, aminoaryl, acryl or epoxy third oxyalkyl in a kind of.R
2Specifically can be preferably from vinyl, N-(2-amino-ethyl), acryl, methacryloyl, acryl propyl group, methacryloyl propyl group, 3-aminopropyl, 3-glycidoxy, 3-glycidoxy propyl group, 3-glycidoxy ethyl, 3-glycidoxy methyl, 3-chloropropyl methyl, 3-chloropropyl ethyl, 3-bromopropyl methyl, 3-bromopropyl ethyl, 2-(3; 4-epoxy group(ing) cyclohexyl) methyl, 2-(3; 4-epoxy group(ing) cyclohexyl) ethyl, 2-(3,4-epoxy group(ing) cyclohexyl) propyl group; More preferably a kind of in vinyl, N-(2-amino-ethyl), acryl propyl group, 2-(3, the 4-epoxy group(ing) cyclohexyl) ethyl; But R of the present invention
2Be not limited to above-mentioned group.The concrete structure of general formula (3) is listed, but the present invention is not limited to this:
Among the present invention, R
3Be preferably methyl, R
4Be preferably ethyl.
A kind of preparation method of organosiloxane polymer, it may further comprise the steps:
(a) synthetic intermediate: by the monomer of the monomer of following general formula (2) and general formula (3) under the effect of acid catalyst in water and solvent, under nitrogen atmosphere through the synthetic multipolymer midbody of polycondensation with formula (4):
R
1Si (OR
3)
3General formula (2)
R
2 mSi (OR
4)
4-mGeneral formula (3)
M representes the natural number less than 4, and the n value is 5～300; Wherein catalyst consumption is the 0.005-3% of monomer (2) and monomer (3) gross weight, and the consumption of general formula (2) is the 20-80 weight part; The consumption of general formula (3) is the 80-20 weight part, and the consumption of water is the 10-300 weight part, and the consumption of solvent is the 100-700 weight part;
(b) midbody is handled: after above-mentioned reaction finished, by product was gone out in underpressure distillation, adds normal hexane again and separates out midbody, obtain having general formula behind the suction filtration midbody of (4);
(c) synthetic product: by structural formula be following general formula (5) monomer and general formula (6) monomer and general formula (4) midbody in solvent, have the product of general formula (1) under the nitrogen atmosphere through the preparation of acid catalysis electrophilic addition reaction:
CH
2=CHOCH
2X general formula (5)
CH
2=CHOCH
2Y general formula (6)
general formula (1)
Midbody in the reaction (4) is 10 with the mass ratio of monomer (5) or monomer (6): 1-500: 1, and catalyst consumption accounts for the 0.01-0.5 weight part in the addition reaction substrate, and solvent load is 5-20 a times of addition substrate weight; In the above-mentioned general formula, the X that is wherein occurred representes the Ar base, and Y representes the Ar base; R
1Expression straight chain or graft copolymer; R
2The expression alkylene, contain the N alkyl, contain a kind of in O alkyl or the halogen atom alkyl; R
3Expression hydrogen or methyl; R
4Expression methyl or ethyl; The n value is 5～300.
In the preferred scheme, in (a) of the present invention step, acid catalyst is hydrochloric acid, sulfuric acid, nitric acid, tosic acid hydrate, a kind of in toluene boric acid, ethyl sulfate, the organic sulfonic acid alkyl ester, but is not limited to above-mentioned acid; This reaction process can by through change acid catalyst kind, consumption, and the interpolation pattern control; Consumption at above-mentioned reacting middle catalyst is comparatively suitable scope for the 100-700 weight part, and the interpolation pattern of acid catalyst is to add control through constant pressure funnel.
Said solvent is a kind of in acetone, THF, benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ETHYLE ACETATE, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, the DPG methyl ether.Wherein catalyst consumption is the 0.005-3% of monomer (2) and monomer (3) gross weight, if be that speed of reaction is low excessively because less than 0.005%, hydrolysis is difficult to fully, with the carrying out that has influence on down the one-step polycondensation reaction and the electrophilic addition reaction in following step; If greater than 3%, speed of reaction is too high, and the polycondensation in following step can not be carried out.
In said (c) step; Acid catalyst is formic acid, acetate, phenylformic acid, Whitfield's ointment, tartrate, oxalic acid, Succinic Acid, thiazole-4 carboxylic acid, pyridine-3 carboxylic acid, pyridine-4 carboxylic acid, oxygen carboxylic acid fluoride, oxyacetic acid, thiocarboxylic acid, Cyclopentane carboxylic acid, cyclopropane dicarboxylic acid, contains carboxylic acid fluoride, pyridazine carboxylic acid, imidazolyl carboxylic acid; Propyl sulfonic acid, butyl sulfonic acid, sulfanilic acid, α-Nai Huangsuan, beta-naphthalenesulfonic-acid, 2-aminoethyl sulfonic acid, Phenylsulfonic acid, tosic acid, 4-chlorobenzene boric acid, a kind of in toluene boric acid, silicic acid, sulfuric acid, hydrochloric acid, Hydrogen bromide, phosphoric acid, phosphorous acid, the nitric acid; Catalyst consumption is between 0.01-0.5 part of addition reaction substrate mass parts.If because less than 0.01 part, the carbonium ion intermediate product in the middle of the reaction is not enough, and addition reaction is difficult to fully; If greater than 0.5 part, can hinder monomer (5), the reaction of compound that monomer (6) is represented and midbody (4).
Said solvent is a kind of in acetone, THF, benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ETHYLE ACETATE, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, the DPG methyl ether.
In the preferred scheme, in said (c) step, the dimension of addition reaction between 120-200 ℃, preferably 150-180 ℃.If when being lower than 120 ℃, electrophilic addition reaction carries out not exclusively; If when being higher than 200 ℃, surpass monomer (4) probably or/and the boiling point of the compound of the structural unit of monomer (5) expression causes the substrate volatilization, reduced the transformation efficiency of polycondensation.More preferred, temperature of reaction is 150-180 ℃, and best temperature of reaction is 180 ℃.
A kind of colored filter is used the chromatic photoresist agent, and it is the following component that comprises in weight part:
In the above-mentioned chromatic photoresist agent, said pigment dispersion color paste is in pigment, to add dispersion agent or/and the dispersion aids solubilizing agent mixes, and the preferred blending ratio (mass ratio) of three is 1: 0.05-0.4: 80-85; Wherein pigment is pigment dyestuff, is preferably red PR177, PR254, yellow PY139, PY150, green PG36, PG58, blue PB156, purple PV23, PV37 pigment; Chromatic photoresist agent of the present invention can form red pixel, green pixel and the blue pixel etc. of filter aptly according to the difference of the color of the pigment dyestuff of selecting for use.And the dispersing of pigments system is stable and have pixel light resolving power preferably in the time of in this scope; Dispersion agent in the mill base or dispersion aids; Can improve the stability of coloured composition; Obtain suitable liquid viscosity and surface tension; As pigment dispersing agent, preferably can use carboxylicesters, the salt of HMW poly carboxylic acid, the long-chain of hydroxyl to gather a kind of in urethane, modified polyurethane, modified polyacrylate, polyether ester type anionic promoting agent, polyxyethylated SULPHOSUCCINIC ACID ESTER, the pigment derivative etc. among the present invention.Wherein solvent is one or more mixing in methylethylketone, ethyl cellosolve, glycol dimethyl ether, ethylene glycol diethyl ether, Propylene Glycol Dimethyl Ether, diethylene glycol dimethyl ether, 2-oxyethyl group propyl alcohol, 2-methoxypropanol, 3-methoxybutanol, pimelinketone, ketopentamethylene, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, the butylacetate etc., but the present invention is not limited only to this.
In the above-mentioned colored Photoresist; The selection of said connection material will consider that it has caustic solubility; Therefore require to have the caustic solubility group on its structure; As preferably, a kind of in connection material methylacrylic acid according to the invention and butyl methacrylate copolymer, methylacrylic acid and cyclohexyl methacrylate multipolymer, methylacrylic acid and cyclohexyl methacrylate and styrol copolymer, methylacrylic acid and cyclohexyl methacrylate and methylacrylic acid-2-hydroxy methacrylate multipolymer, methylacrylic acid and cyclohexyl methacrylate and vinylbenzene and methylacrylic acid-2-hydroxy methacrylate multipolymer; The acid number that connects material is 70KOH/g-150KOH/g; Acid number surpasses under the situation of 150KOH/g, and acrylics is excessive to the solvability of alkali, and development proper range (development width) narrows down; On the other hand, if less than 70KOH/g, cause development time to elongate to alkali poorly soluble, this is disadvantageous on technology.
In the above-mentioned colored Photoresist, said phtotpolymerizable monomer is one or more mixing in pentaerythritol triacrylate, Dipentaerythritol diacrylate, Dipentaerythritol triacrylate, Dipentaerythritol five propenoate, the dipentaerythritol acrylate etc.Monomeric consumption is selected very important, when phtotpolymerizable monomer consumption possibly cause by the pixel edge of chromatic photoresist agent preparation during less than 0.1 weight part irregular in each component; And when monomer content was higher than 30 weight parts, this chromatic photoresist agent was then developed difficult in developing solution even can not be developed.
In the above-mentioned colored Photoresist; Said initiator is selected from 2; 4-trichloromethyl (4 '-p-methoxy-phenyl)-6-triazine, 2,4-trichloromethyl-(4 '-methoxyl-styrene)-6-triazine, 2,2 '-two (2-chloro-phenyl-) 4; 4 '; 5, a kind of in 5 '-tetraphenyl bisglyoxaline, second phthalein benzene compound (Irg-369), 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, 2-methyl-(4-methylbenzene sulfenyl)-2-beautiful jade-1-propane-1-ketone (Irg-907) and 2-phenmethyl-2-dimethylamino-1-(the 4-beautiful jade phenyl)-butane-1-ketone etc., but be not limited to above-mentioned several kinds.In order to guarantee that photoresist can carry out good polymerizing curable; And reach stronger tack, and the consumption of initiator must be controlled within the suitable scope, and monomeric photopolymerization reaction is insufficient in light reaction procedure when initiator amount is less than 0.1 weight part in each component; The initiator that when initiator amount is higher than 3 weight parts, has neither part nor lot in reaction is then stayed in the photoresist; Make the loss of transmission of system, so among the present invention, the consumption of initiator is between the 0.1-3 weight part.
In the above-mentioned colored Photoresist, described auxiliary agent can further be selected from one or more in photosensitizers tinting material curing catalyst, heat polymerization suppressor factor, softening agent, sensitizing agent, skimmer, adhesion promotor, the filler etc.Auxiliary agent consumption be the 0.1-1 weight part in the chromatic photoresist agent; When auxiliary dosage surpasses 1 weight part, when coating is dry, be easy to generate surface irregularity, smoothness worsens easily.
In the above-mentioned colored Photoresist; Described solvent is selected from one or more in methylethylketone, ethyl cellosolve, glycol dimethyl ether, ethylene glycol diethyl ether, Propylene Glycol Dimethyl Ether, diethylene glycol dimethyl ether, 2-oxyethyl group propyl alcohol, 2-methoxypropanol, 3-methoxybutanol, pimelinketone, ketopentamethylene, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, the butylacetate etc., but the present invention is not only for above-mentioned several kinds.
A kind of colored filter, it comprises on the glass substrate that has black matrix, the glass substrate and is coated with three layers of chromatic photoresist agent pattern of pixels as claimed in claim 10 that three layers of chromatic photoresist agent pattern of pixels are followed successively by three kinds of colors of red, green, blue.
A kind of manufacturing method of color filters, it may further comprise the steps:
A) processing substrate: on glass substrate, form black matrix;
B) color filter manufacturing: coating red Photoresist as claimed in claim 10 covers black matrix and forms the color film of the first layer on above-mentioned glass substrate, more successively through mask shelter, partial exposure, development, cure step form the first layer pixel; Repeat above-mentioned steps again and form green with the blue second layer and the 3rd layer of pixel respectively, be made into colored filter at last.
Specifically making according to following step, at first glass substrate is cleaned, is that the carbon family organic materials of 3.5-5 deposits on the glass substrate with optical density(OD) then, and after this, utilizing photolithography is the black matrix of glass substrate formation figure; Black matrix can be provided with like this: the edge section of unit picture element will correspond to each other with the zone that is used to be provided with TFT, so that can be blocked in the light that the light source in the unsettled zone of electric field sends; The chromatic photoresist agent of the present invention that the coating thickness scope is about 1-3 μ m on the whole surface of glass substrate afterwards utilizes spin-coating method or the flat red color film of method coating the first layer that is coated with to glass substrate, with the black matrix of thorough covering; Except the specific region of the color film of the first layer, (be and form figure and remaining areas); Shelter the whole surface of the color film of the first layer with the opaque section of mask; Through the UV rayed (generally speaking the color film of the first layer is carried out partial exposure; The chromatic photoresist layer of filter has the negative characteristic of the unexposed portion that can remove the chromatic photoresist agent, so just make public through the transparent part of mask in the specific region that is used to form chromatic photoresist agent figure); Afterwards, will be dipped in the developing solution, adopt infusion method or spraying process to develop, remove its unexposed portion, then under 230 ℃ temperature, let the red color film of the first layer harden through the red color film of the first layer that exposure has changed the photochemistry structure; On the whole surface on the glass substrate that comprises the first layer red pixel layer, be coated with second layer green tint film then, according to carrying out partial exposure, development, sclerosis, formation second layer pixel layer with the step of the first layer pixel; The 3rd layer of blue color film of coating carries out partial exposure to it on the whole surface of the glass substrate that comprises first and second layers of pixel then, develops, and sclerosis finally forms colored filter.
Compare prior art, beneficial effect of the present invention is:
1. organo-siloxane high molecular polymer of the present invention; Join in the middle of chromatic photoresist agent (Color Resist) prescription; Can substitute flow agent and coupling agent simultaneously, make prescription simplify, with other resins and polarity of solvent in compatibility more aspect the matching degree;
2. the chromatic photoresist agent of the present invention's making, the intramolecularly pressure difference Δ F between the double-deck interface that the color film of coating and substrate form is controlled, thereby realizes the colloid retraction is controlled, and forms even and the little coating that bounces back;
3. the chromatic photoresist agent made of the present invention, when making the color film of coating realize planarization, pixel lines on the colored filter and alignment mark all can be good sticks adherence;
4. the liquid crystal display device colored filter of the present invention and method of manufacture thereof making can realize that color is even; Make liquid crystal panel and do not have the pressure uneven phenomenon; The pixel adherence well reaches performances such as high precision.
Below in conjunction with accompanying drawing and embodiment the present invention is done further explain.
Description of drawings
Fig. 1 representes in the comparative example table 1, from the edge thickness data acquisition of the monochromatic sheet of contrast experiment (1)-(7) in a system of coordinates, wherein, edge thickness be 3 times of thickness with interior data results, development posterior border noresidue when making band pixel line bar print;
Fig. 2 representes Comparative Examples (2) when making band pixel line bar print, the electromicroscopic photograph that has pixel to come off;
Fig. 3 representes Comparative Examples (5) when making band pixel line bar print, the electromicroscopic photograph that has marker to come off;
Fig. 4 representes Comparative Examples (7) when making band pixel line bar print, the electromicroscopic photograph that pixel and marker all do not come off.
Embodiment
Below be preferred concrete embodiment and the comparative example of the present invention.
Embodiment [1]
Get 1.62 parts of BYK-302 (polyether-modified YSR 3286), 6.49 parts of the compounds shown in the chemical formula 3-2; 20 parts of pimelinketone; Add in the four-hole boiling flask, and in four-hole boiling flask, put into magneton, device prolong, TM; Be communicated with nitrogen, be installed on the four-hole boiling flask behind 3 parts of sulfuric acid (60% concentration) constant pressure funnel of packing into, the 80rpm stirring velocity inserts in the 70 degree water-baths reacted 2 hours; Underpressure distillation removed by product in 0.5 hour, was cooled to 50 degree, continued reaction 8 hours; Finish reaction, add 60 parts of normal hexanes, make product separate out; Cloth formula funnel suction filtration, drying obtains midbody 4-1.
Embodiment [2]
Get 3.24 parts of Ciba-EFKA-3883 (two key end capped polyether modified organic silicon), and 3.61 parts of the compounds represented of 1.26 parts of the compounds represented of above-mentioned chemical formula 3-1 and 5-6; 20 parts of pimelinketone; Add in the four-hole boiling flask, and in four-hole boiling flask, put into magneton, the device prolong, TM is communicated with nitrogen; 3 parts of moisture nitric acid (1000ppm) are packed into and are installed on the four-hole boiling flask behind the constant pressure funnel, and the 240rpm stirring velocity inserted in the 60 degree water-baths reaction 2 hours, and underpressure distillation removed by product in 0.5 hour; Be cooled to 50 degree, continue reaction 8 hours, finish reaction; Add 60 parts of normal hexanes; Make product separate out, cloth formula funnel suction filtration, drying obtains midbody 4-2.
Embodiment [3]
Get each 1.62 parts of Ciba-EFKA-3883 (two key end capped polyether modified organic silicon) and Ciba-EFKA-3034 (fluorine-containing carbon organic silicon modified by polyether), and 4.87 parts of the compounds represented of above-mentioned chemical formula 3-2; 20 parts of pimelinketone; Add in the four-hole boiling flask, and in four-hole boiling flask, put into magneton, device prolong, TM; Be communicated with nitrogen, be installed on the four-hole boiling flask behind 3 parts of sulfuric acid (60% concentration) constant pressure funnel of packing into, the 120rpm stirring velocity inserts in the 60 degree water-baths reacted 2 hours, and underpressure distillation removed by product in 0.5 hour; Be cooled to 50 degree, continue reaction 8 hours, finish reaction, add 60 parts of normal hexanes; Make product separate out, cloth formula funnel suction filtration, drying obtains midbody 4-3.
Embodiment [4]
Product midbody 4-1, and 0.62 part of the compound represented of above-mentioned chemical formula 5-2; PMA30 part; 0.03 part oxalic acid; Add in the four-hole boiling flask, put into magneton, device prolong, constant pressure funnel, TM; Be communicated with nitrogen, the 120rpm stirring velocity inserts in the 120 degree oil baths reacted 6 hours, finished reaction, obtained the compound 1-1 of general formula (1) expression.
Embodiment [5]
Product midbody 4-2, and 0.20 part of the compound represented of 0.42 part of the compound represented of above-mentioned chemical formula 5-6 and chemical formula 5-2; PMA30 part; 0.01 part beta-naphthalenesulfonic-acid; Add in the four-hole boiling flask, put into magneton, device prolong, constant pressure funnel, TM; Be communicated with nitrogen, the 120rpm stirring velocity inserts in the 170 degree oil baths reacted 6 hours, finished reaction, obtained the compound 1-2 of general formula (1) expression.
Embodiment [6]
Product midbody 4-3, and 0.42 part of the compound represented of above-mentioned chemical formula 5-2; PMA30 part; 0.01 part beta-naphthalenesulfonic-acid; Add in the four-hole boiling flask, put into magneton, device prolong, constant pressure funnel, TM; Be communicated with nitrogen, the 120rpm stirring velocity inserts in the 150 degree oil baths reacted 6 hours, finished reaction, obtained the compound 1-3 of general formula (1) expression.
Embodiment [7]
Stirred 5 hours, and promptly processed the chromatic photoresist agent in the clean container of packing into after the use 800nm aperture strainer pressure filtration; Wherein skimmer is the BYK-057 that German Bi Ke company produces.
(Comparative Examples)
Below; With green photoresist is example, on glass substrate, is coated with monochromatic color film, at this moment; Can form two interfaces: one is the air-resist interface of the upper surface formation of air and color film, and another is the lower surface of color film and the resist-glass interface that glass substrate forms; Be in color membrane molecule on the interface with to be in the molecular attraction that the dispersed system interior molecules receives different, produced surface tension F
Air-resistAnd surface tension (being wetting tension) F
Resist-glassThe internal pressure of condensed matter is the 10^5 order of magnitude of the internal pressure of gaseous substance, so F
Air-resistJust equal the internal pressure of the color membrane molecule of upper epidermis, it is inner that direction is pointed to color film; The F that makes a concerted effort to be of the internal pressure of the internal pressure of glass and the color membrane molecule in following top layer
Glass-resist, because the solid internal pressure is greater than liquid internal pressure power, so F
Glass-resistSensing glass is inner; And the power that the color membrane molecule in following top layer receives is F
Glass-resistReactive force, i.e. tension force F
Resist-glass, and size and F
Glass-resistEquate that it is inner that direction is pointed to color film; So, F
Air-resistAnd F
Resist-glassBe a pair of tension force in the opposite direction, their making a concerted effort is intramolecularly pressure difference Δ F; Common F
Air-resisT is less than F
Resist-glass, Here it is, and photoresist can natural mobile hydromeehanics reason.
Prescription with embodiment [7] is the basis, does not add the blank test example (1) as a comparison of compound and the flow agent and the coupling agent of general formula (1); The compound that does not add general formula (1) is formed Comparative Examples (2)--(4) with flow agent or/and coupling agent joins in the prescription of embodiment [7] respectively; Do not add flow agent or/and coupling agent, respectively with compound 1-1,1-2,1-3 add in the middle of the prescription of embodiment [7], form Comparative Examples (5)--(7).The monochromatic color film substrate of direct back baking after making the monochromatic filter (a) of band pixel afterwards respectively and not adding mask exposure; So both can detect the pixel adhesion property; The thickness data of energy measurement retraction and the thickness data at edge again; Surveying instrument uses SE500-59 type roughness tester, result 1 (the thickness unit: μ m) that sees the following form
Table 1
| Simultaneous test | General formula (1) | Flow agent | Coupling agent | Thickness | Edge thickness | Adherence |
| (1) | ?-- | -- | -- | 1.102 | 6.823 | ● |
| (2) | ?-- | Fluorine carbon | -- | 1.043 | 4.225 | ● |
[0088]
| (3) | -- | -- | Siloxanes | 1.072 | 6.457 | Zero |
| (4) | -- | Siloxanes | Siloxanes | 1.170 | 2.849 | △ |
| (5) | 1-1 | -- | -- | 1.085 | 2.551 | △ |
| (6) | 1-2 | -- | -- | 1.007 | 3.122 | Zero |
| (7) | 1-3 | -- | -- | 1.114 | 2.243 | Zero |
Annotate: ● the remarked pixel lines have the △ of coming off remarked pixel lines not come off, but Marker has come off zero remarked pixel and Marker all not to come off.
Claims (14)
1. an organosiloxane polymer is characterized in that, has the high molecular polymer of the structural unit of formula (1) expression:
General formula (1)
In the said general formula (1), X representes the Ar base, and Y representes the Ar base; R
1Expression straight chain or graft copolymer; R
2The expression alkylene, contain the N alkyl, contain a kind of in O alkyl or the halogen atom alkyl; R
3Expression hydrogen or methyl; R
4Expression methyl or ethyl; The n value is 5～300.
2. organosiloxane polymer according to claim 1 is characterized in that the structure that said X representes is selected from C
6～C
30Ar base, Y representes C
6～C
30Ar base, X is identical group or different group with Y.
3. organosiloxane polymer according to claim 1 is characterized in that, the C that said X representes
6～C
18Phenyl, alkyl phenyl or alkoxyl phenyl, Y representes C
6～C
18Phenyl, alkyl phenyl or alkoxyl phenyl.
4. organosiloxane polymer according to claim 1 is characterized in that, said R
1Expression C
2～C
30Saturated straight chain or graft copolymer.
5. organosiloxane polymer according to claim 1 is characterized in that, said R
1Expression C
2～C
16Alkyl, polyester based, alkyl, polyether base or polyester polyether-based.
6. organosiloxane polymer according to claim 1 is characterized in that, said R
2Expression C
2～C
16Vinyl, aminoalkyl group, aminoaryl, acryl or epoxy third oxyalkyl in a kind of.
7. the preparation method of an organosiloxane polymer is characterized in that, it may further comprise the steps:
(a) synthetic intermediate: by the monomer of the monomer of following general formula (2) and general formula (3) under the effect of acid catalyst in water and solvent, under nitrogen atmosphere through the synthetic multipolymer midbody of polycondensation with formula (4):
R
1Si (OR
3)
3General formula (2)
R
2 mSi (OR
4)
4-mGeneral formula (3)
M representes the natural number less than 4, and the n value is 5～300;
(b) midbody is handled: after above-mentioned reaction finished, by product was gone out in underpressure distillation, adds normal hexane again and separates out midbody, obtain having general formula behind the suction filtration midbody of (4);
(c) synthetic product: by structural formula be following general formula (5) monomer and general formula (6) monomer and general formula (4) midbody in solvent, have the product of general formula (1) under the nitrogen atmosphere through the preparation of acid catalysis electrophilic addition reaction:
CH
2=CHOCH
2X general formula (5)
CH
2=CHOCH
2Y general formula (6)
In the above-mentioned general formula, the X that is wherein occurred representes the Ar base, and Y representes the Ar base; R
1Expression straight chain or graft copolymer; R
2The expression alkylene, contain the N alkyl, contain a kind of in O alkyl or the halogen atom alkyl; R
3Expression hydrogen or methyl; R
4Expression methyl or ethyl; The n value is 5～300.
8. the preparation method of this organosiloxane polymer according to claim 7; It is characterized in that; In said (a) step; Acid catalyst is hydrochloric acid, sulfuric acid, nitric acid, tosic acid hydrate, a kind of in toluene boric acid, ethyl sulfate, the organic sulfonic acid alkyl ester, and said solvent is a kind of in acetone, THF, benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ETHYLE ACETATE, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, the DPG methyl ether.
9. the preparation method of kind of organosiloxane polymer according to claim 7; It is characterized in that; In said (c) step; Acid catalyst is formic acid, acetate, phenylformic acid, Whitfield's ointment, tartrate, oxalic acid, Succinic Acid, thiazole-4 carboxylic acid, pyridine-3 carboxylic acid, pyridine-4 carboxylic acid, oxygen carboxylic acid fluoride, oxyacetic acid, thiocarboxylic acid, Cyclopentane carboxylic acid, cyclopropane dicarboxylic acid, contains carboxylic acid fluoride, pyridazine carboxylic acid, imidazolyl carboxylic acid; Propyl sulfonic acid, butyl sulfonic acid, sulfanilic acid, α-Nai Huangsuan, beta-naphthalenesulfonic-acid, 2-aminoethyl sulfonic acid, Phenylsulfonic acid, tosic acid, 4-chlorobenzene boric acid, a kind of in toluene boric acid, silicic acid, sulfuric acid, hydrochloric acid, Hydrogen bromide, phosphoric acid, phosphorous acid, the nitric acid; Solvent is a kind of in acetone, THF, benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ETHYLE ACETATE, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, the DPG methyl ether.
10. a colored filter is used the chromatic photoresist agent, is characterised in that, it is the following component that comprises in weight part:
11. colored filter according to claim 10 is used the chromatic photoresist agent, is characterised in that, said pigment dispersion color paste is in pigment, to add dispersion agent or/and the dispersion aids solubilizing agent mixes.
12. colored filter according to claim 10 is used the chromatic photoresist agent; Be characterised in that said connection material is a kind of in methylacrylic acid and butyl methacrylate copolymer, methylacrylic acid and cyclohexyl methacrylate multipolymer, methylacrylic acid and cyclohexyl methacrylate and styrol copolymer, methylacrylic acid and cyclohexyl methacrylate and methylacrylic acid-2-hydroxy methacrylate multipolymer, methylacrylic acid and cyclohexyl methacrylate and vinylbenzene and the methylacrylic acid-2-hydroxy methacrylate multipolymer; The acid number that connects material is 70KOH/g-150KOH/g.
13. colored filter; It is characterized in that; It comprises on the glass substrate that has black matrix, the glass substrate and is coated with three layers of chromatic photoresist agent pattern of pixels as claimed in claim 10 that three layers of chromatic photoresist agent pattern of pixels are followed successively by three kinds of colors of red, green, blue.
14. a manufacturing method of color filters is characterized in that it may further comprise the steps:
A) processing substrate: on glass substrate, form black matrix;
B) color filter manufacturing: the as claimed in claim 10 red Photoresist of first kind of color of coating covers black matrix and forms the color film of the first layer on above-mentioned glass substrate, more successively through mask shelter, partial exposure, development, cure step form the first layer pixel; Repeat above-mentioned steps again and form green with blue second layer pixel and the 3rd layer of pixel respectively, be made into colored filter at last.
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Cited By (4)
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| CN103275617A (en) * | 2013-05-17 | 2013-09-04 | 涌奇材料技术（上海）有限公司 | Preparation method and application of organosilicon photo-diffusion particle |
| CN105037627A (en) * | 2015-08-21 | 2015-11-11 | 深圳市联深化学技术有限公司 | Oligomeric resin, preparation method thereof and application thereof in color photoresist |
| CN110036318A (en) * | 2016-12-08 | 2019-07-19 | 夏普株式会社 | The manufacturing method of black matrix composition, black matrix and black matrix |
| CN120904744A (en) * | 2025-10-10 | 2025-11-07 | 信联电子材料科技股份有限公司 | Anti-reflection coating composition and preparation method thereof |
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| US6046283A (en) * | 1996-12-31 | 2000-04-04 | Massachusetts Institute Of Technology | Rubber-modified rigid silicone resins and composites produced therefrom |
| JP2004300311A (en) * | 2003-03-31 | 2004-10-28 | Fuji Photo Film Co Ltd | Coating composition for forming silica film and method for forming silica film |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103275617A (en) * | 2013-05-17 | 2013-09-04 | 涌奇材料技术（上海）有限公司 | Preparation method and application of organosilicon photo-diffusion particle |
| CN103275617B (en) * | 2013-05-17 | 2016-03-02 | 涌奇材料技术（上海）有限公司 | The preparation method of organosilicon photo-diffusion particle and application thereof |
| CN105037627A (en) * | 2015-08-21 | 2015-11-11 | 深圳市联深化学技术有限公司 | Oligomeric resin, preparation method thereof and application thereof in color photoresist |
| CN110036318A (en) * | 2016-12-08 | 2019-07-19 | 夏普株式会社 | The manufacturing method of black matrix composition, black matrix and black matrix |
| CN110036318B (en) * | 2016-12-08 | 2021-10-08 | 夏普株式会社 | Composition for black matrix, black matrix, and manufacturing method of black matrix |
| CN120904744A (en) * | 2025-10-10 | 2025-11-07 | 信联电子材料科技股份有限公司 | Anti-reflection coating composition and preparation method thereof |
| CN120904744B (en) * | 2025-10-10 | 2025-12-16 | 信联电子材料科技股份有限公司 | An anti-reflective coating composition and its preparation method |
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