CN105934712A - Photosensitive resin composition for color filter and color filter using same - Google Patents
Photosensitive resin composition for color filter and color filter using same Download PDFInfo
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- CN105934712A CN105934712A CN201480073417.9A CN201480073417A CN105934712A CN 105934712 A CN105934712 A CN 105934712A CN 201480073417 A CN201480073417 A CN 201480073417A CN 105934712 A CN105934712 A CN 105934712A
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- Prior art keywords
- pigment
- photosensitive resin
- resin composition
- chemical formula
- functionalized resins
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
Provided are a photosensitive resin composition and a color filter using the same, the composition comprising: (A) an acrylic binder resin; (B) a photopolymerizable monomer; (C) a photopolymerization initiator; (D) a pigment dispersion containing a functional resin and a pigment, the functional resin including at least one repeating unit represented by chemical formula 1, at least one repeating unit represented by chemical formula 2, at least one repeating unit represented by chemical formula 3 and at least one repeating unit represented by chemical formula 4; and (E) a solvent.
Description
Technical field
It relates to be used for the photosensitive resin composition of light filter and use its light filter (color filter, colorized optical filtering
Sheet, color filter).
Background technology
Light filter is used for liquid crystal display (LCD), the optical filter etc. of photographing unit.Light filter can be by charge-coupled image sensor
Or the thin district (fine region) of coating three kinds or more kind color dyes manufactures on transparency carrier.The thin film of this coloring
Manufacture with methods such as pigment dispersion method.
By pigment dispersion method for the color photosensitive resin compositions manufacturing light filter generally include adhesive resin, can
Photo polymerization monomer, Photoepolymerizationinitiater initiater, coloring agent, solvent, other additives etc..For coloring agent, it is used mostly pigment dispersion
Body.Such as, by mixing red pigment and the red pigment dispersion that obtains of yellow uitramarine for realizing the redness picture of light filter
Element, and by mixing viridine green and the viridine green dispersion that obtains of yellow uitramarine for realizing the green picture of light filter
Element.
Recently, light filter is by can the continuous processing of large-scale production produce.Additionally, due to recently according to height
Quality specification requires that light filter has the color characteristics of excellence, thermostability etc., has the most made and has strengthened the pigment as coloring agent
Trial to improve light characteristic.
Summary of the invention
Technical purpose
One embodiment provides the absorbance owing to improving and high brightness and high-contrast and has the face of excellence
The photosensitive resin composition of color characteristic.
Another embodiment provides the light filter using photosensitive resin composition to manufacture.
Technical Solving
One embodiment provides photosensitive resin composition, and it includes (A) acryl adhesive resin (acryloyl group
Class adhesive resin, acryl-based binder resin);(B) photopolymerizable monomer;(C) Photoepolymerizationinitiater initiater;(D) bag
Include dispersible pigment dispersion (pigment dispersion, the pigment dispersion of functionalized resins (functional resins, functional resin) and pigment
Liquid, pigment dispersion liquid, pigment dispersion liquid), this functionalized resins includes being represented by chemical formula 1
At least one repetitive, at least one repetitive represented by chemical formula 2, at least one weight of representing by chemical formula 3
Multiple unit and at least one repetitive represented by chemical formula 4;And (E) solvent.
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
(in chemical formula 1 to chemical formula 4,
R1To R8It is hydrogen or substituted or unsubstituted C1 to C10 alkyl group independently, and
L1To L4It is singly-bound or substituted or unsubstituted C1 to C10 alkylidene group independently.)
Functionalized resins can include the repetitive represented by chemical formula 5.
[chemical formula 5]
(in chemical formula 5,
A, b, c and d are the integer of 1 or bigger independently.)
The weight average molecular weight of functionalized resins can be in the range of 5,000g/mol to 30,000g/mol.
In including the dispersible pigment dispersion of functionalized resins and pigment, pigment can include the official adsorbed on the surface of the pigment
Resin can be changed.
Pigment can include organic pigment, inorganic pigment or combinations thereof.
Pigment can include viridine green.
Pigment can utilize functionalized resins to carry out surface process, and photosensitive resin composition can include 3wt% extremely
The acryl adhesive resin of 10wt%;The photopolymerizable monomer of 3wt% to 13wt%;The photopolymerization of 0.1wt% to 3wt%
Initiator;2wt% to 10wt% utilizes the pigment that functionalized resins surface processes;And the solvent of surplus.
Photosensitive resin composition can comprise at least one additive in following further: malonic acid, 3-amino-
1,2-propylene glycol, there is vinyl groups or the silane coupling agent of (methyl) acryloxy group, levelling agent (leveling
Agent), fluorine class surfactant and radical polymerization initiator.
By pulverizing pigment and the pigment of pulverizing can be mixed with functionalized resins it is prepared by functionalized resins table
The pigment that face processes.
The pigment pulverized can include the pigment pulverized and functionalized resins are added solvent with the mixing of functionalized resins
To prepare solution and to be dried this solution.
The pigment pulverized and functionalized resins can mix with the weight ratio of 10:4 to 10:2.
Mixing can be carried out at a temperature of 20 DEG C to 70 DEG C.
Another embodiment provides the light filter using the photosensitive resin composition for light filter.
Detailed description below includes other embodiment.
Beneficial effect
Photosensitive resin composition has excellent absorbance and high brightness and high-contrast, thus has the color of excellence
Characteristic, thus can be used for light filter.
Detailed description of the invention
Hereinafter, embodiments of the present invention are described in detail.But, these embodiments are exemplary, the present invention
It is not limited to it and the present invention is to be limited by the scope of claim.
In this manual, when the most additionally provide be specifically defined time, term " substituted " can refer to halogen atom (F, Cl,
Br, I), oh group, C1 to C20 alkoxy base, nitryl group, cyano group, amido, imino group, azido base
Group, amidino groups group, hydrazino group, hydrazono-group, carbonyl group, carbamyl group, mercapto groups, ester group, ether, carboxyl
Group or its salt, sulfonic group or its salt, phosphoric acid or its salt, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynes
Base group, C6 to C30 aromatic yl group, C3 to C20 group of naphthene base, C3 to C20 cycloalkenyl groups, C3 to C20 cycloalkynyl group,
C2 to C20 heterocycloalkyl, C2 to C20 heterocycloalkenyl group, C2 to C20 heterocycle alkynyl group, C3 to C30 heteroaryl groups
Or combinations thereof replaces at least one hydrogen.
In this manual, when the most additionally offer is specifically defined, term " miscellaneous " can refer to at least the one of N, O, S and P
Individual hetero atom replaces at least one C in cyclic substituents.
In this manual, when the most additionally provide be specifically defined time, " (methyl) acrylate " refer to " acrylate " and
Both " methacrylate ", and " (methyl) acrylic acid " refers to " acrylic acid " and " methacrylic acid ".
In this manual, when the most additionally offer is specifically defined, term " combines " and refers to mixing or copolymerization.
In this manual, it is specifically defined unless otherwise provided, should when not drawing chemical bond in place of should providing
Position has been bonded hydrogen atom.
In this manual, when the most additionally offer is specifically defined, " * " represents the identical or different atom of connection or chemistry
The point of formula.
Photosensitive resin composition according to embodiment includes (A) acryl adhesive resin;(B) photopolymerization list
Body;(C) Photoepolymerizationinitiater initiater;(D) including the dispersible pigment dispersion of functionalized resins and pigment, this functionalized resins includes by chemistry
Formula 1 represent at least one repetitive, chemical formula 2 at least one repetitive represented, represented at least by chemical formula 3
A kind of repetitive and at least one repetitive represented by chemical formula 4;And (E) solvent.
Photosensitive resin composition according to embodiment includes functionalized resins and pigment, such as, use functionalized resins surface
Process pigment, such that it is able to suppression pigment coalescence and improve pigment dispersion and therefore improve color characteristic such as absorbance with
Brightness etc..
Functionalized resins includes the repetitive represented by chemical formula 1 to chemical formula 4.
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
(in chemical formula 1 to chemical formula 4,
R1To R8It is hydrogen or substituted or unsubstituted C1 to C10 alkyl group independently, and
L1To L4It is singly-bound or substituted or unsubstituted C1 to C10 alkylidene group independently.)
In the exemplary embodiment, functionalized resins can include the repetitive represented by chemical formula 5.
[chemical formula 5]
(in chemical formula 5,
A, b, c and d are the integer of 1 or bigger independently.)
The weight average molecular weight of functionalized resins can be 5,000g/mol to 30,000g/mol.
Functionalized resins includes the circulus with larger molecular weight such that it is able to improve with this functionalized resins surface
The thermostability of the pigment processed.
In this pigment processed with functionalized resins surface, functionalized resins can adsorb the surface at pigment.Permissible
Functionalization is prepared by pigment and functionalized resins being mixed in a solvent with the weight ratio of 10:4 to 10:2 and remove solvent
Resin absorption pigment from the teeth outwards.
Hereinafter, will be described in every kind of component.
(D) pigment
Pigment can include organic pigment, inorganic pigment or combinations thereof.Such as, pigment can be viridine green.
It is by being tiny microgranule by bigger granules of pigments pulverizing generally, due to pigment, i.e. by Crushing of Ultrafine method
Using, pigment particle can easily coalesce, such that it is able to add pigment derivative etc. in the dispersive process of pigment wherein
To suppress the coalescence of pigment.Pigment derivative can have with pigment class as structure or physics and adsorb the most well
Structure in surface of pigments thus suppress the coalescence of pigment particle.
But, pigment derivative can have in the dispersive process of pigment the color different from pigment or coalesce each other from
And deteriorate the dispersion of pigment.
Pigment according to embodiment can be by using functionalized resins, i.e. includes the weight represented by chemical formula 1 to 4
The resin of multiple unit processes with higher efficiency surface after the pulverizing, thus effectively suppresses the coalescence of pigment particle.
Functionalized resins physics and chemically adsorb on the surface of pigment particle and prevent the absorption of pigment particle, and
Additionally, the dispersant described afterwards additionally adsorbs the surface not adsorbing other pigment particles thereon at functionalized resins
On, such that it is able to improve the dispersion of pigment.Accordingly, because pigment particle coalesces the most each other, decrease light scattering, such that it is able to change
Kind absorbance.
The surface using the pigment of functionalized resins processes and can include pulverizing pigment and by the pigment pulverized and functionalization
Mixed with resin.
Specifically, the pigment of pulverizing can include adding pigment and the functionalized resins of pulverizing with the mixing of functionalized resins
Enter solvent to prepare solution and to be then dried this solution.
In this article, can with the pigment of the weight ratio co-grinding of 10:4 to 10:2 and functionalized resins, and additionally,
Mixing can be carried out at 20 DEG C to 70 DEG C.
Pigment can include, such as pink group pigment (red-based pigment), blue class pigment, green class pigment,
Purple class pigment, yellow class pigment, cyanine class pigment, aubergine class pigment, black pigment etc..
Pink group pigment can be perylene kinds pigment, Anthraquinones pigment, dianthranide quinones pigment, azo pigment, weight
Nitrogen class pigment, quinacridone-type pigments, anthracene class pigment etc..The instantiation of pink group pigment can be perylene pigment, quinoline
Quinacridone pigment, naphthols AS, Sicomin pigment, anthraquinone (the Sudan I, II, III, R), dianthraquinone ester/salt, bisazo (visible idol
Nitrogen, vis azo) .alpha.-5:6-benzopyran etc..
The example of blue class pigment can be metal phthalocyanine class pigment, indanthrone (indanthone) class pigment, indophenols
Pigment etc..The instantiation of blue class pigment can include phthalocyanine metal complex compound such as C.I. Pigment Blue 15 (CuPc, copper
Phthalocyanine), chloro C.I. Pigment Blue 15, chloro aluminum phthalocyanine, titanyl phthalocyanine, vanadic acid phthalocyanine, magnesium phthalocyanine, ZnPc, ferrum phthalein
Cyanines, cobalt phthalocyanine etc..
Green class pigment can include halogenated phthalocyanines class pigment etc..Specifically, it includes many chlorine C.I. Pigment Blue 15, many chlorine bromine phthalocyanine
Such as Green 58 etc..
Purple class pigment can include that diazine is purple, the first purple B (first violet B), crystal violet, indanthrene are bright
Purple (indanthrene brilliant violet) etc..
Yellow class pigment can be tetrachloroisoindolinone class pigment, Hansom (hansa) class pigment, benzidine yellow class face
Material, azo pigment etc..Specifically, yellow class pigment can include Hansa yellow (10G, 5G, 3G, G, GR, A, RN, R), benzidine
(G, GR), chrome yellow, permanent yellow (FGL, H10G, HR) etc..
Cyanine class pigment can include nonmetal phthalocyanine, merocyanine (merocyanine) etc..
Reddish violet class pigment can include dimethylquinacridone, thioindigoid etc..
Black pigment can be nigrosine, perylene is black, titanium is black, carbon black etc..
Described above, in addition to processing with functionalized resins surface, pigment can use with dispersant, thus pigment can
To disperse well.
Dispersant can be non-ionic dispersing agent, anionic dispersing agents, cation dispersing agent etc..The instantiation of dispersant
Can be poly alkylene glycol and esters, polyoxyalkylene, polyol ester alkylene oxide addition compound product, the oxidation of alcohol alkylidene
Thing addition compound product (alcohol alkylene oxide addition product), sulphonic acid ester, sulfonate, carboxylate, carboxylic acid
Salt, alkylamide alkylene oxide addition compound product, alkylamine etc..Can come individually or as the mixture of two or more
Use these.
The example of commercially available dispersant can include by BYK Co., Ltd. manufacture DISPERBYK-101,
DISPERBYK-130、DISPERBYK-140、DISPERBYK-160、DISPERBYK-161、DISPERBYK-162、
DISPERBYK-163、DISPERBYK-164、DISPERBYK-165、DISPERBYK-166、DISPERBYK-170、
DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 etc.;By EFKA Chemicals
Co. EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, the EFKA-450 etc. manufactured;By
The Solsperse 5000 of Zeneka Co. manufacture, Solsperse 12000, Solsperse 13240, Solsperse
13940、Solsperse 17000、Solsperse 20000、Solsperse 24000GR、Solsperse 27000、
Solsperse 28000 etc.;PB711, the PB821 etc. manufactured by Ajinomoto Inc.
Total amount based on the photosensitive resin composition for light filter, can include point with the amount of 0.01wt% to 15wt%
Powder.When including dispersant within the range, due to the dispersive property improved, the photosensitive resin composition for light filter has
There are stability, developability and the pattern Forming ability of excellence.
In this article, in photosensitive resin composition, pigment can be included with dispersion.Prepare pigment dispersion
Solvent can be acetic acid glycol ester, ethyl cellosolve, propylene glycol methyl ether acetate (propylene glycol
Methyletheracetate), ethyl lactate, Polyethylene Glycol, Ketohexamethylene, propylene glycol monomethyl ether etc..Based on photosensitive resin composition
Total amount, the amount of dispersible pigment dispersion can be 20wt% to 40wt%, such as 30wt% to 40wt%.
The mean diameter of pigment can be in the range of 5nm to 150nm, such as 10nm to 70nm.Mean diameter when pigment
When this scope, it is possible to achieve high-contrast and the thermostability of excellence and light resistance.
Total amount based on photosensitive resin composition, can be with 2wt% to 10wt%, and the amount of such as 5wt% to 8wt% includes
The pigment processed with functionalized resins surface.When including pigment in this range, color characteristics can be improved and at identical color
High brightness and contrast can be realized under coordinate.
(A) acryl adhesive resin
Photosensitive resin composition according to embodiment includes acryl adhesive resin.
Acryl adhesive resin is the first ethylenically unsaturated monomers (first ethylenic unsaturated
And the copolymer of second ethylenically unsaturated monomers copolymerizable with it, and be to comprise at least one acrylic acid monomer)
The resin of class repetitive.
First ethylenically unsaturated monomers is the ethylenically unsaturated monomers including at least one carboxyl.The example of this monomer
Including acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid or combinations thereof.
Total amount based on acryl adhesive resin, can be with 5wt% to 50wt%, such as 10wt% to 40wt%'s
Amount includes the first ethylenically unsaturated monomers.
Second ethylenically unsaturated monomers can be aromatic vinyl compound such as styrene, α-methyl styrene, ethylene
Base toluene, vinyl benzyl methyl ether etc.;Unsaturated carboxylic ester compound such as (methyl) acrylic acid methyl ester., (methyl) acrylic acid second
Ester, (methyl) butyl acrylate, (methyl) acrylic acid 2-hydroxy methacrylate, (methyl) acrylic acid 2-hydroxybutyl, (methyl) propylene
Acid benzyl ester, (methyl) cyclohexyl acrylate, (methyl) phenyl acrylate etc.;Unsaturated carboxylic acid aminoalkyl ester compounds such as (first
Base) acrylic acid 2-amino ethyl ester, (methyl) acrylic acid 2-dimethylaminoethyl etc.;Vinyl esters of carboxylic acids compound such as vinyl acetate
Base ester, vinyl benzoate etc.;Unsaturated carboxylic acid epihydric alcohol ester compound such as (methyl) glycidyl acrylate etc.;Second
Thiazolinyl cyanide such as (methyl) acrylonitrile etc.;Unsaturated acyl amines such as (methyl) acrylamide etc.;Like this.Can be single
Mixture solely or as two or more uses these.
The instantiation of acryl adhesive resin can be polybenzyl methacrylate, (methyl) acrylic acid/methyl
Benzyl acrylate copolymer, (methyl) acrylic acid/benzyl methacrylate/styrol copolymer, (methyl) acrylic acid/methyl-prop
Olefin(e) acid benzyl ester/HEMA copolymer, (methyl) acrylic acid/benzyl methacrylate/styrene/methyl-prop
Olefin(e) acid 2-hydroxyethyl ester copolymer etc., but it is not limited to this.Can be used this individually or as the mixture of two or more
A bit.
Acryl adhesive resin can have about 3,000g/mol to about 150,000g/mol, and e.g., from about 5,000g/
The weight average molecular weight of mol to 30,000g/mol.When weight average molecular weight in the range of acryl adhesive resin has this,
Photosensitive resin composition for light filter can have the process based prediction model of excellence and suitable viscosity, keeps suitable
Developability and sensitivity, and the excellent close contact performance to substrate is shown during manufacturing light filter.
Acryl adhesive resin can have about 50mgKOH/g to 200mgKOH/g, e.g., from about 80mgKOH/g extremely
The acid number of 150mgKOH/g.When acid number in the range of acryl adhesive resin has this, pixel has the resolution of excellence
Rate.
Total amount based on the photosensitive resin composition for light filter, can be with 3wt% to 15wt%, and such as 5wt% is extremely
The amount of 10wt% comprises acryl adhesive resin.When including acryl adhesive resin within the range, improve
Sensitivity and developability, and due to the chemical resistance improved, there is not the pattern of stripping.
(B) photopolymerizable monomer
Photopolymerizable monomer can be to include at least one ethylenic unsaturated double-bond (methyl) acrylic acid simple function
Or multifunctional ester.
Photopolymerizable monomer has ethylenic unsaturated double-bond, thus can draw in the process-exposed of patterning process
Play enough polymerizations and formation has excellent thermostability, light resistance and chemical-resistant pattern.
The instantiation of photopolymerizable monomer can be two (methyl) acrylic acid glycol ester, two (methyl) acrylic acid diethyl
Diol ester, two (methyl) acrylic acid triglycol ester, two (methyl) acrylic acid propylene glycol ester, two (methyl) acrylic acid neopentyl glycol
Ester, two (methyl) acrylic acid 1,4-butanediol ester, two (methyl) acrylic acid 1,6-HD ester, two (methyl) acrylic acid bisphenol-A
Ester, two (methyl) acrylate, pentaerythritol, three (methyl) acrylate, pentaerythritol, four (methyl) acrylic acid tetramethylolmethane
Ester, six (methyl) acrylate, pentaerythritol, two (methyl) acrylic acid dipentaerythritol ester, three (methyl) acrylic acid two season penta 4
Alcohol ester, five (methyl) acrylic acid dipentaerythritol ester, six (methyl) acrylic acid dipentaerythritol ester, bisphenol-A epoxy (methyl) third
Olefin(e) acid ester, glycol monoethyl ether (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, tricresyl phosphate (methyl) third
Alkene trimethylammonium ester, (methyl) acrylic acid phenolic and epoxy ester etc..
The example of commercially available reactive unsaturated compound is as follows.Simple function (methyl) acrylate can include(Toagosei Chemistry Industry Co.,Ltd.);
KAYARAD(Nippon Kayaku Co.,Ltd.); (Osaka
Organic Chemical Ind., Ltd.) etc..The example of difunctionality (dysfunctional) (methyl) acrylate can wrap
Include Aronix(Toagosei Chemistry Industry Co., Ltd.),
KAYARAD (Nippon Kayaku Co., Ltd.),(Osaka Organic Chemical Ind., Ltd.) etc..Trifunctional (methyl) propylene
The example of acid esters can include Aronix
(Toagosei Chemistry Industry Co., Ltd.), KAYARAD (Nippon Kayaku Co., Ltd.), (Osaka Yuki Kayaku Kogyo Co.Ltd.)
Deng.Can be used these individually or as the mixture of two or more.
Photopolymerizable monomer can be processed to improve developability with anhydride.
Total amount based on the photosensitive resin composition for light filter, can be with 3wt% to 13wt%, and such as 4wt% is extremely
The amount of 10wt% includes photopolymerizable monomer.When including photopolymerizable monomer within the range, sudden and violent at patterning process
During dew, photopolymerizable monomer fully solidifies, and has the reliability of excellence and can improve the development for alkaline-based developer
Property.
(C) Photoepolymerizationinitiater initiater
Photoepolymerizationinitiater initiater can be acetophenone compounds, benzophenone compound, thiaxanthone compounds, benzene idol
Relation by marriage compounds, compound in triazine class, oxime compound etc..
The example of acetophenone compounds can be 2,2'-diethoxy acetophenone, 2,2'-dibutoxy 1-Phenylethanone., 2-
Hydroxy-2-methyl propiophenone, to tert-butyl group trichloroacetophenone, chloro-to tert-butyl group dichloroacetophenone, 4-chloro-acetophenone, 2,2'-bis-
4-metaphenoxy acetophenone, 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholino acrylate-1-ketone, 2-benzyl-2-dimethylamino-
1-(4-morphlinophenyl)-butyl-1-ketone etc..
The example of benzophenone compound can be benzophenone, benzoylbenzoic acid ester, methyl benzoylbenzoate
(benzoyl benzoate methyl), 4-phenyl benzophenone, dihydroxy benaophenonel, acrylated benzophenone, 4,4'-
Double (diethylamino) benzophenone of double (dimethylamino) benzophenone, 4,4'-, 4,4'-dimethylamino benzophenone, 4,
4'-dichloro benzophenone, 3,3'-dimethyl-2-methoxy benzophenone etc..
The example of thiaxanthone compounds can be thiaxanthone, CTX, 2-methyl thiaxanthone, isopropylthioxanthones
Ketone, 2,4-diethyl thioxanthone, 2,4-diisopropylthioxanthone etc..
The example of benzoin compounds can be benzoin, benzoin methylether, benzoin ethyl ether, benzoin iso-propylether,
Benzoin isobutyl ether, benzyl dimethyl ketal etc..
The example of compound in triazine class can be 2,4,6-trichloto-s-triazine, double (the trichloromethyl)-s-three of 2-phenyl 4,6-
Piperazine, 2-(3', 4'-dimethoxy-styryl)-4,6-double (trichloromethyl)-s-triazine, 2-(4'-methoxyl group naphthyl)-4,6-
Double (trichloromethyl)-s-triazine, 2-(p-methylphenyl)-4,6-double (trichloromethyl)-s-triazine, 2-(p-methylphenyl)-4,6-
Double (the trichloromethyl)-s-triazine of double (trichloromethyl)-s-triazine, 2-xenyl 4,6-, double (trichloromethyl)-6-styryl-
Double (the trichloromethyl)-s-triazine of s-triazine, 2-(naphthalene-1-base)-4,6-, double (three chloromethanes of 2-(4-methoxynaphthalene-1-base)-4,6-
Base)-s-triazine, double (the trichloromethyl)-6-piperonyl-s-triazine of 2,4-, double (trichloromethyl)-6-(the 4-methoxybenzene second of 2,4-
Thiazolinyl)-s-triazine etc..
Oxime compound can include, such as 2-(o-benzoyl oxime)-1-[4-(thiophenyl) phenyl]-1,2-acetyl caproyl,
1-(o-acetyl oxime)-1-[9-ethyl-6-(2-toluyl)-9H-carbazole-3-base] ethyl ketone etc..
In addition to described compound, Photoepolymerizationinitiater initiater may further include carbazole compound, cyclohexadione compounds, boron
Acid sulfonium compounds, diazonium compounds, glyoxaline compound, diimidazole compounds etc..
Total amount based on the photosensitive resin composition for light filter, can be with 0.1wt% to 3.0wt%, such as
The amount of 0.5wt% to 1.0wt% includes Photoepolymerizationinitiater initiater.When including Photoepolymerizationinitiater initiater within the range, in pattern shape
The process-exposed of one-tenth process then occurs enough photopolymerization, it is possible to prevent absorbance from deteriorating due to non-reaction initiator.
(E) solvent
Solvent is and acryl adhesive resin, photopolymerizable monomer, Photoepolymerizationinitiater initiater and use functionalized resins table
The pigment that face processes has the compatibility but the material that do not reacts.
Solvent it is not particularly limited, but it is specifically it may be that such as alcohol such as methanol, ethanol etc.;Ether such as dichloroether, just
Butyl ether, isoamyl ether, methyl phenyl ether, oxolane etc.;Glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol, propylene glycol monomethyl ether
Deng;Cellosolve acetate (cellosolve acetate) is such as methylcellosolve acetate, ethyl cellosolve acetate, diethyl
Cellosolve acetate etc.;Carbitol such as Methylethyl carbitol, diethylene glycol diethyl ether., diethylene glycol monomethyl ether, diethylene glycol list
Ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether etc.;Propylene glycol alkyl ether acetic acid ester is such as
Propylene glycol methyl ether acetate, propylene glycol propyl ether acetas etc.;Aromatic hydrocarbon such as toluene, dimethylbenzene etc.;Ketone such as methyl ethyl ketone, hexamethylene
Ketone, 4-hydroxy-4-methyl-2-pentanone, methyl-positive acetone, methyl-positive butanone, methyl-positive pentanone, 2-heptanone etc.;Saturated fat
Race's monocarboxylic acid Arrcostab such as ethyl acetate, n-butyl acetate, isobutyl acetate etc.;Lactic acid alkyl ester such as methyl lactate, lactic acid second
Ester etc.;Hydroxyacetic acid Arrcostab such as hydroxy methyl acetate, hydroxyl ethyl acetate, Butyl Glycolate etc.;Acetic acid alkoxyalkyl
Ester such as acetic acid methoxyl group methyl ester, methoxy ethyl acetate, methoxy butyl acetate, acetic acid ethyoxyl methyl ester, acetic acid ethyoxyl second
Ester etc.;3-hydroxyalkyl propionate such as 3-hydroxy methyl propionate, 3-hydroxypropionate etc.;3-alkoxypropan acid alkyl ester such as 3-
Methoxy methyl propionate, 3-methoxypropionate, 3-ethoxyl ethyl propionate, 3-ethoxypropanoate etc.;2-hydroxyl third
Acid alkyl ester such as 2 hydroxy propanoic acid methyl ester, 2 hydroxy propanoic acid ethyl ester, 2 hydroxy propanoic acid propyl ester etc.;2-alkoxypropan acid alkyl ester is such as
2-methoxy methyl propionate, 2-methoxypropionate, 2-ethoxyl ethyl propionate, 2-ethoxypropanoate etc.;2-hydroxyl-
2 Methylpropionic acid Arrcostab such as 2-hydroxy-2-methyl methyl propionate, 2-hydroxy-2-methyl ethyl propionate etc.;2-alkoxyl-2-first
Base alkyl propionates such as 2-methoxyl group-2 Methylpropionic acid methyl ester, 2-ethyoxyl-2 Methylpropionic acid ethyl ester etc.;Ester such as propanoic acid 2-hydroxyl
Base ethyl ester, propanoic acid 2-hydroxy-2-methyl ethyl ester, acetic acid hydroxyl ethyl ester, methyl 2-hydroxy-3-methyl butyrate etc.;Or keto acid
Ester such as ethyl pyruvate etc..Furthermore it is also possible to use solvent such as N-METHYLFORMAMIDE, DMF, N-methyl first
Anilide, N-methylacetamide, N,N-dimethylacetamide, N-Methyl pyrrolidone, dimethyl sulfoxide, benzylisoeugenol, two
Hexyl ether, acetylacetone,2,4-pentanedione, isophorone, caproic acid, octanoic acid, 1-capryl alcohol, 1 nonyl alcohol, benzylalcohol, benzyl acetate, ethyl benzoate, grass
Diethyl phthalate, ethyl maleate., gamma-butyrolacton, ethylene carbonate, propylene carbonate, ethylene glycol monophenyl ether acetas etc..Permissible
Mixture individually or as two or more uses them.
In view of intersolubility and reactivity, it may be preferred to use glycol ethers such as ethylene glycol monoethyl ether etc.;Ethylene glycol alkyl ether
Acetas such as ethyl cellosolve acetate etc.;Ester such as propanoic acid 2-hydroxy methacrylate etc.;Diethylene glycol such as diethylene glycol monomethyl ether etc.;Third
Glycol alkyl ether acetas such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetas etc..
Using solvent with surplus, the 40wt% of such as based on the photosensitive resin composition for light filter total amount is extremely
90wt%.When including solvent within the range, due to viscosity suitable during manufacturing light filter, for the light of light filter
Photosensitive resin composition has the machinability of improvement.
(F) other additives
Photosensitive resin composition for light filter may further include other additive such as malonic acid, 3-amino-1,
2-propylene glycol;Including vinyl groups or the coupling agent of (methyl) acryloxy group, levelling agent;Fluorine class surfactant,
Radical polymerization initiator, to prevent the stain in coating procedure or stain, regulation homogenizing, or prevents due to undeveloped pattern
Residual.
Depend on desired performance, the consumption of additive can be controlled.
Coupling agent can be silane coupling agent, and the example of silane coupling agent can be trimethoxysilyl
Benzoic acid, γ-methacryloxypropyl trimethoxy silane, vinyltriacetoxy silane, vinyl trimethoxy
Silane, γ-isocyanates propyl-triethoxysilicane, γ-glycidoxypropyltrimewasxysilane, β-(3,4-epoxy
Cyclohexyl) ethyl trimethoxy silane etc..Individually or can be used these with the mixture of two or more.
The photosensitive resin compositions for light filter based on 100 weight portions, the amount of silane coupling agent can specifically be
0.01 weight portion is to 1 weight portion.
As required, the photosensitive resin composition for light filter can further include fluorine class surfactant.
The example of fluorine class surfactant can be F-482, F-484, F-478, F-554 etc. of DIC Co., Ltd., but
It is not limited to this.
Total amount based on photosensitive resin composition, can be with 0.01wt% to 5wt%, and preferably 0.1wt% is extremely
The amount of 2wt% includes fluorine class surfactant.When using fluorine class surfactant outside this range, compositions is coated
Journey uneven distribution can have the film of uniform thickness from without being formed.
Photosensitive resin composition according to embodiment can be can be solidified by radiant light and can use alkaline aqueous solution
The alkali developable of development.When by photosensitive resin composition substrate overlaminate and by actinic ray radiate with formed be used for colour filter
During the pattern of sheet, photosensitive resin composition is reacted by actinic ray, thus drastically deteriorates reaction zone compared with non-reaction zone
Dissolubility, consequently only that non-reaction zone can optionally be dissolved.In this way, the solution removing non-exposed region is referred to as aobvious
Shadow liquid, and this developer solution is categorized as two types such as organic solvent type and alkali developable.Owing to organic solvent type developer solution draws
Play atmospheric pollution and human body is damaged, alkali developable solution can be used in terms of environment.Photosensitive tree according to embodiment
Oil/fat composition uses alkali developable solution, thus can use in terms of environment.
The light filter using above photosensitive resin composition to manufacture is embodiment there is provided according to another.
The method manufacturing light filter is as follows.
In a suitable approach if the coating photosensitive resin compositions such as spin coating, roller coat, spraying are to form 0.5 on the glass substrate
μm is to the resin composition layer of 10 μ m-thick.
Subsequently, will there is the substrate of resin composition layer by light radiation to form the pattern needed for light filter.Can pass through
Using UV, electron beam or X-ray radiate as light source, and can be, such as 190nm to 450nm, and specifically
The region of 200nm to 400nm radiates UV.Can radiate by further using photoresist mask.With this
After method carries out radiative process, process the resin composition layer being exposed to light source with developer solution.In this article, resin composition layer
In non exposed region dissolve and form the pattern of light filter.That can this process be repeated as necessary number of colours is secondary
Number, it is thus achieved that there is the light filter of desired pattern.Additionally, when the picture pattern obtained by the development in above procedure is by again
When heating or solidify to its radiation actinic ray, crack resistance, solvent resistance etc. can be improved.
Hereinafter, the present invention is illustrated in greater detail with reference to embodiment.But, these embodiments should be not by any way
It is construed as limiting the scope of the invention.
(pigment processed with functionalized resins surface)
Preparation embodiment 1
By fine for 15g pigment (Green 58, DIC Co., Ltd.), the repetition including being represented by chemical formula 6 of 3g
Unit also has the resin of molecular weight of about 12,000g/mol and the propylene glycol methyl ethyl acetas of 82ml as solvent
(Sigma-Aldrich Co., Ltd.) mixes and then while stirring at 40 DEG C with homogenizer or mechanical agitator
Kneading.After kneading, it is dried at room temperature for removing solvent by gains.
[chemical formula 6]
(pigment dispersion)
Preparation embodiment 2
Then, pigment, dispersant and the acrylic adhesives that will process with the functionalized resins surface of preparation embodiment 1
It is dissolved in according in the solvent of consisting of, and agitating solution.
Pigment according to preparation embodiment 1: 15wt%
Dispersant (BYK2102, BYK): 6wt%
Acrylic adhesives (100S, SMS): 5wt%
Solvent (propylene glycol methyl ethyl acetas, Sigma-Aldrich Co., Ltd.): 74wt%
Preparation embodiment 3
Pigment, dispersant and acrylic adhesives are dissolved in according in the solvent of consisting of, and agitating solution.
Pigment (Green 58, DIC Co., Ltd.): 15wt%
Dispersant (BYK2102, BYK): 3.5wt%
Acrylic adhesives (100S, SMS): 3wt%
Solvent (propylene glycol methyl ethyl acetas, Sigma-Aldrich Co., Ltd.): 78.5wt% is (for light filter
Photosensitive resin composition)
Embodiment 1 and comparative example 1
With the composition provided in table 1, Photoepolymerizationinitiater initiater is dissolved in following solvent, and solution is at room temperature stirred
Mix one hour.With the composition provided in table 1, acryl adhesive resin and following acrylic compounds photopolymerizable monomer are added
Enter wherein, and mixture is stirred at room temperature 2 hours.With the composition provided in table 1, fluorine class surfactant is added thereto,
And the mixture obtained is stirred at room temperature one hour.With the composition provided in table 1, dispersible pigment dispersion is added thereto, will
Mixture is stirred at room temperature 2 hours, and by solution filter three times to remove impurity, manufacture according to embodiment 1 and comparative example 1
Every kind of photosensitive resin composition.As follows for manufacturing the component of photosensitive resin composition.
(A) acryl adhesive resin (polybenzylmethacrylate resin (NPR 1520), Miwon
Commercial Co.,Ltd)
(B) acrylic compounds photopolymerizable monomer (double pentaerythritol methacrylate (DPHA), Nippon Kayaku
Co.Ltd.)
(C) Photoepolymerizationinitiater initiater (oxime compound (CGI-124, BASF))
(D) dispersible pigment dispersion
(D-1) according to the dispersible pigment dispersion of preparation embodiment 2
(D-2) according to the dispersible pigment dispersion of preparation embodiment 3
(E) solvent (propylene glycol methyl ethyl acetas, Sigma-Aldrich Co., Ltd.)
(F) fluorine class surfactant (F-554, DIC Co., Ltd.)
Table 1
(unit: wt%)
Assessment: the spectral characteristic of photosensitive resin composition
By every kind of photosensitive resin composition according to embodiment 1 and comparative example 1 by using coating equipment (MIKASA
Co., Ltd.) coat on the glass substrate to 3.0 μm to 4.0 μ m-thick and at 90 DEG C on hot plate be dried with obtain every kind
Film.The film obtained is exposed with the exposure dose of 100mJ/cm2 and toasts 30 minutes under the oven conditions of 230 DEG C.By making
The absorbance of film, chromaticity coordinates and bright is measured with spectrophotometer (Otsuka Electronics Co., Ltd., MCPD 3000)
Degree, provides result in table 2.
Table 2
With reference to table 2, use the photosensitive resin composition of embodiment 1 of the pigment according to embodiment compared with comparative example 1
Show high brightness and excellent absorbance.
Although the present invention is described already in connection with the illustrative embodiments being presently believed to be practicality, but should manage
Solving, the present invention is not limited to disclosed embodiment, but, on the contrary, it is intended to cover be included in the spirit of claims
Arrange with the various amendments in scope and equivalent.Therefore, aforementioned embodiments is construed as exemplary rather than with any
Mode limits the present invention.
Claims (12)
1. a photosensitive resin composition, comprises:
(A) acryl adhesive resin;
(B) photopolymerizable monomer;
(C) Photoepolymerizationinitiater initiater;
(D) dispersible pigment dispersion, described dispersible pigment dispersion includes that functionalized resins and pigment, described functionalized resins include by chemistry
Formula 1 represent at least one repetitive, chemical formula 2 at least one repetitive represented, represented at least by chemical formula 3
A kind of repetitive and at least one repetitive represented by chemical formula 4;And
(E) solvent:
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
Wherein, in chemical formula 1 to chemical formula 4,
R1To R8It is hydrogen or substituted or unsubstituted C1 to C10 alkyl group independently, and
L1To L4It is singly-bound independently, or substituted or unsubstituted C1 to C10 alkylidene group.
Photosensitive resin composition the most according to claim 1, wherein, described functionalized resins comprises and is represented by chemical formula 5
Repetitive:
[chemical formula 5]
Wherein, in chemical formula 5,
A, b, c and d are the integer of 1 or bigger independently.
Photosensitive resin composition the most according to claim 1, wherein, the weight average molecular weight of described functionalized resins 5,
In the range of 000g/mol to 30,000g/mol.
Photosensitive resin composition the most according to claim 1, wherein, described pigment comprise organic pigment, inorganic pigment or
Combinations thereof.
Photosensitive resin composition the most according to claim 1, wherein, described pigment comprises viridine green.
Photosensitive resin composition the most according to claim 1, wherein, described pigment utilizes described functionalized resins to carry out table
Face processes, and
Described photosensitive resin composition comprises
The described acryl adhesive resin of 3wt% to 15wt%;
The described photopolymerizable monomer of 3wt% to 13wt%;
The described Photoepolymerizationinitiater initiater of 0.1wt% to 3wt%;
2wt% to 10wt% utilizes the described pigment that described functionalized resins surface processes;And
The described solvent of surplus.
Photosensitive resin composition the most according to claim 1, wherein, described photosensitive resin composition comprises further and is selected from
At least one following additive: malonic acid;3-amido-1,2-propanediol;There is vinyl groups or (methyl) acryloyl-oxy
The silane coupling agent of base group;Levelling agent;Fluorine class surfactant;And radical polymerization initiator.
Photosensitive resin composition the most according to claim 1, wherein, the described pigment including described functionalized resins disperses
Liquid is prepared by following
Pulverize pigment;And
The described pigment pulverized is mixed with functionalized resins.
Photosensitive resin composition the most according to claim 8, wherein, described by the described pigment pulverized and functionalized resins
Mixing includes
The described pigment pulverized and described functionalized resins are added to solvent to prepare solution;And
It is dried described solution.
Photosensitive resin composition the most according to claim 8, wherein, with the weight ratio co-grinding of 10:4 to 10:2
Described pigment and described functionalized resins.
11. photosensitive resin compositions according to claim 8, wherein, described in be blended at a temperature of 20 DEG C to 70 DEG C
OK.
12. 1 kinds use the filter manufactured according to the photosensitive resin composition according to any one of claim 1 to claim 11
Color chips.
Applications Claiming Priority (3)
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KR10-2014-0006222 | 2014-01-17 | ||
KR20140006222A KR101486570B1 (en) | 2014-01-17 | 2014-01-17 | Photosensitive resin composition and color filter using the same |
PCT/KR2014/003515 WO2015108240A1 (en) | 2014-01-17 | 2014-04-22 | Photosensitive resin composition for color filter and color filter using same |
Publications (1)
Publication Number | Publication Date |
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CN105934712A true CN105934712A (en) | 2016-09-07 |
Family
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CN201480073417.9A Withdrawn CN105934712A (en) | 2014-01-17 | 2014-04-22 | Photosensitive resin composition for color filter and color filter using same |
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KR (1) | KR101486570B1 (en) |
CN (1) | CN105934712A (en) |
WO (1) | WO2015108240A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115124889A (en) * | 2022-08-31 | 2022-09-30 | 山东凯瑞尔光电科技有限公司 | Red color paste for color photoresist and preparation method thereof |
CN115637060A (en) * | 2021-07-19 | 2023-01-24 | 三星Sdi株式会社 | Pigment dispersion, photosensitive resin composition comprising same, photosensitive resin layer, color filter, and display device |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08259876A (en) * | 1995-03-24 | 1996-10-08 | Japan Synthetic Rubber Co Ltd | Organic pigment dispersed liquid for color filter |
TWI300795B (en) | 2001-08-21 | 2008-09-11 | Mitsubishi Chem Corp | Curable resin composition for die coating and process for producing color filter |
JP4064681B2 (en) * | 2002-02-14 | 2008-03-19 | 富士フイルム株式会社 | Pigment dispersant, pigment dispersion composition containing the same, and colored photosensitive composition |
JP4384570B2 (en) * | 2003-12-01 | 2009-12-16 | 東京応化工業株式会社 | Photoresist composition for thick film and method for forming resist pattern |
KR20090031987A (en) * | 2007-09-26 | 2009-03-31 | 후지필름 가부시키가이샤 | Pigment dispersion composition, photocurable composition, color filter, liquid crystal display element, solid state image sensor and method for manufacturing color filter |
CN101978004B (en) * | 2008-03-17 | 2013-11-06 | 富士胶片株式会社 | Pigment-dispersed composition, colored photosensitive composition, photocurable composition, color filter, liquid crystal display element, and solid image pickup element |
KR20100072934A (en) * | 2008-12-22 | 2010-07-01 | 제일모직주식회사 | Photosensitive resin composition for color filter and color filter using same |
JP5597616B2 (en) * | 2011-10-03 | 2014-10-01 | 富士フイルム株式会社 | Negative chemically amplified resist composition, and resist film, resist-coated mask blank, resist pattern forming method, and photomask using the same |
-
2014
- 2014-01-17 KR KR20140006222A patent/KR101486570B1/en not_active IP Right Cessation
- 2014-04-22 WO PCT/KR2014/003515 patent/WO2015108240A1/en active Application Filing
- 2014-04-22 CN CN201480073417.9A patent/CN105934712A/en not_active Withdrawn
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115637060A (en) * | 2021-07-19 | 2023-01-24 | 三星Sdi株式会社 | Pigment dispersion, photosensitive resin composition comprising same, photosensitive resin layer, color filter, and display device |
CN115124889A (en) * | 2022-08-31 | 2022-09-30 | 山东凯瑞尔光电科技有限公司 | Red color paste for color photoresist and preparation method thereof |
CN115124889B (en) * | 2022-08-31 | 2022-11-22 | 山东凯瑞尔光电科技有限公司 | Red color paste for color photoresist and preparation method thereof |
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WO2015108240A1 (en) | 2015-07-23 |
KR101486570B1 (en) | 2015-01-26 |
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