CN101526740A - Low-temperature curable photosensitive resin composition - Google Patents
Low-temperature curable photosensitive resin composition Download PDFInfo
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- CN101526740A CN101526740A CN200910008090A CN200910008090A CN101526740A CN 101526740 A CN101526740 A CN 101526740A CN 200910008090 A CN200910008090 A CN 200910008090A CN 200910008090 A CN200910008090 A CN 200910008090A CN 101526740 A CN101526740 A CN 101526740A
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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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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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
- G03F7/0005—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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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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
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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
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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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
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Abstract
The invention provides a low-temperature curable photosensitive resin composition, which can be totally cured at the low-temperature, and can be used to produce the curing film with excellent heat resistance and chemical resistance and at the same time the gas is generated less, and the aforementioned curing film can be used as the color filter of flat-panel display. The invention is characterized that the photosensitive resin composition contains (A) the epoxy resins used as the binder resins and alkali-soluble resin which chosen from one or more of the acrylate resin, photopolymer resins and the mixture of those resins, (B) epoxy hardener, (C) the cross-linking monomer with double keys of alkene, (D) coloring agent, (E) photoplymerization and (F) dissolvent.
Description
Technical field
The photosensitive polymer combination of the color filter that is used for flat-panel monitor (colorfilter) that the present invention relates to solidify at low temperatures.
Background technology
The manufacturing of filter substrate generally includes: utilize Cr/CrO
xForm black matrix (black matrix), utilize the pigment dispersing method to form color filter and form common electrode.
Similarly pass through reactive sputtering (reactive sputtering) with Cr/CrO with electric crystal array film (TFT-array (array)) operation
xEvaporation utilizes optics (photo) engineering to be formed for realizing the RGB pattern of color after forming the black matrix pattern on the glass substrate through cleaning.Usually, move same mask and form the RGB pattern, owing to can stop when utilizing the photopolymerization reaction of exposure to acquire a certain degree, therefore in order to continue to utilize the polyreaction of heat, cure (post-bake) after implementing separately, utilize dipping (dipping) during development, soak (puddle), shower (shower), spraying (spray) method etc. of putting.Carry out the formation of common electrode behind the formation RGB pattern, common electrode is used to make liquid crystal cell (cell) and pixel electrode (pixel electrode) common actions that is formed at the TFT substrate of bottom, by sputter come evaporation ITO (ITO be the transparency and electric conductivity well, the transparent electrode material of chemical stability and excellent heat stability), do not form pattern in addition as the ITO of common electrode.For the protection and the planarization of RGB pattern, also using acrylic resin, polyimide before forming common electrode sometimes is that resin forms planarization film (over coat).
In the color filter operation, under the situation of RGB pattern, mainly utilize rotary coating, slot coated (slit coater) to be coated with, expose, develop after the prebake (pre-bake).After the development, apply at last heat more than 220 ℃ after cure operation, normally used glass can be out of shape under this temperature hardly, and the plastics that are used for flexibility (flexible) display serious deformation can occur in the temperature more than 220 ℃.
Its result cures the temperature of operation after having to reduce in order to reduce substrate deformation, and if the temperature of curing after reducing, just can full solidification, gas generated can increasing, thus image retention not only appears, also can cause problems such as chemical resistance and thermotolerance variation.
Disclose a kind of photosensitive polymer combination in the following patent documentation 1, it has excellent thermotolerance and chemical resistance owing to containing the epoxide of handling through acid anhydrides.But, even contain the described photosensitive polymer combination of the epoxide of handling through acid anhydrides, when curing operation after carrying out under the low temperature below 200 ℃, because chemical resistance and thermotolerance do not reach standard, gas generated increase, thereby the problem that image retention occurs still exists.
Patent documentation 1: Republic of Korea's patent disclosure 2002-0048675 number
Summary of the invention
Therefore, the object of the present invention is to provide a kind of photosensitive polymer combination that is suitable for forming the color filter of flat-panel monitor, it at low temperatures also can full solidification, can make not only less gas generated and has excellent thermotolerance and chemical-resistant cured film.
To achieve these goals, the invention provides a kind of photosensitive polymer combination, it contains:
(A) as (i) epoxy resin of binder resin and (ii) alkali soluble resins, described alkali soluble resins is more than one the resin that is selected among the potpourri of acrylate resin, photopolymer resin and these resins;
(B) epoxy hardener;
(C) has the cross-linkable monomer of alkene double bond;
(D) pigment;
(E) Photoepolymerizationinitiater initiater; With
(F) solvent.
Use photosensitive polymer combination of the present invention, utilize low-temperature setting operation below 200 ℃ also can access gas generated less, the cured film with reliability of thermotolerance and chemical resistance excellence.And, by utilizing described photosensitive polymer combination, can develop in alkaline aqueous solution, the cured film pattern that can access sensitivity and excellent in resolution, have excellent in shape can be at the industrial flat-panel monitor that the high color filter of reliability is provided effectively and contains this color filter.
Description of drawings
Fig. 1 is presented at the figure that the cured film that will be obtained by the photosensitive polymer combination that embodiment 1 and comparative example 1 are made in the experimental example is immersed in the measurement result of the absorbance of the material of back stripping in the nmp solution.
Embodiment
Photosensitive polymer combination of the present invention is characterised in that, owing to contain alkali-soluble acrylate resin or photopolymer resin and epoxy resin and epoxy hardener, has improved the degree of cure that utilizes heat.Therefore, have excellent thermotolerance and chemical-resistant cured film even the curing process of photosensitive polymer combination of the present invention by low temperature also can provide, and the rerum natura of the cured film that obtains of the rerum natura of this cured film and curing process through high temperature there is not difference.
In the photosensitive polymer combination of the present invention, described epoxy resin (composition (A) (i)) has been given play to the effect of the degree of cure that improves photosensitive polymer combination, according to the difference of hardening agent kind, can provide multifrequency natures such as to shorten set time in low-temperature setting.And, to compare with other resin, its cure shrinkage is few, and chemical resistance and thermotolerance etc. are also excellent.
As described epoxy resin, can enumerate the potpourri of bisphenol A type epoxy resin, bisphenol f type epoxy resin, line style phenol aldehyde type epoxy resin, cresols line style phenol aldehyde type epoxy resin and these resins.As commercially available product, bisphenol A type epoxy resin can be enumerated Epikote 1001,1002,1003,1004,1007,1009,1010,828 (oiling シ
エLe エ Port キ シ Co., Ltd. makes) etc., bisphenol f type epoxy resin can be enumerated Epikote 807,834 (oiling シ
エLe エ Port キ シ Co., Ltd. makes) etc., the line style phenol aldehyde type epoxy resin can be enumerated Epikote 152,154,157H65 (oiling シ
エLe エ Port キ シ Co., Ltd. makes), EPPN-201, EPPN-501N, EPPN-501H, EPPN-502N, EPPN-501HY, EOCN-1020 (Nippon Kayaku K. K's manufacturing) etc., cresols line style phenol aldehyde type epoxy resin can be enumerated EOCN-102S, EOCN-103S, EOCN-104S, EOCN-1020, EOCN-1025, EOCN-1027 (Nippon Kayaku K. K's manufacturing), Epikote180S75 (oiling シ
エLe エ Port キ シ Co., Ltd. makes) etc., other epoxy resin can be enumerated NC-3000, NC-3000H (Nippon Kayaku K. K's manufacturing), CY175, CY177, CY179 (vapour Ba-Jia Ji company (CIBA-GEIGYAG) makes).
General assembly (TW) with photosensitive polymer combination is a benchmark, described epoxy resin preferably uses with the amount of 1 weight %～30 weight %, the consumption of described epoxy resin surpasses under the situation of 30 weight %, development can go wrong, and be less than under the situation of 1 weight %, the degree of cure under the low temperature may reduce.
In the photosensitive polymer combination of the present invention, consider that from the aspect of the flexibility of dried photosensitive polymer combination the glass transition temperature that described acrylate resin (composition (A) (ii)) has below 150 ℃ suits.Described acrylate resin obtains by in solvent unsaturated carboxylic acid, aromatic monomer, surface flexible being given with monomer and other polymerizable acrylic monomers.
Described unsaturated carboxylic acid uses for giving alkali-soluble purpose, as its concrete example, can enumerate the acid anhydrides of acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, vinyl acetic acid, above-mentioned acid and the potpourri of these compounds etc.The content of described unsaturated carboxylic acid in macromolecule is preferably 20 weight %～50 weight %, at this moment, if the content of unsaturated carboxylic acid surpasses 50 weight %, then be easy to gelation during polymerization, the degree of polymerization is regulated and is become difficult, the content of unsaturated carboxylic acid cause the storage stability of photosensitive polymer combination to worsen, if then the elongated shortcoming of development time can occur less than 20 weight % in developing procedure.
Described aromatic monomer uses for the chemical resistance and the stable on heating purpose that improve formed photosensitive polymer combination.As the example of described aromatic monomer, can enumerate the potpourri of styrene, benzyl methacrylate, benzyl acrylate, phenyl acrylate, phenyl methacrylate, acrylic acid-2-nitro phenyl ester or acrylic acid-4-nitro phenyl ester, methacrylic acid-2-nitro phenyl ester or methacrylic acid-4-nitro phenyl ester, methacrylic acid-2-nitrobenzyl ester or methacrylic acid-4-nitrobenzyl ester, acrylic acid-2-chlorobenzene ester or acrylic acid-4-chlorobenzene ester, methacrylic acid-2-chlorobenzene ester or methacrylic acid-4-chlorobenzene ester and these compounds etc.The content of described aromatic monomer in macromolecule is preferably 15 weight %～45 weight %, more preferably 20 weight %～40 weight %.If the content of described aromatic monomer surpasses 45 weight %, the flexibility that then forms film when filming reduces, generation is to the shortcoming of the permanance deterioration of substrate, if the content of aromatic monomer is less than 15 weight %, then in developing procedure, reduce with the adaptation of substrate, the phenomenon of peeling off of pattern becomes seriously, and the rectilinear propagation of formed pattern worsens, and is difficult to realize stable pattern.
Give example with monomer as described surface flexible, can enumerate the potpourri etc. of methacrylate, methacrylic acid isotridecyl ester, methacrylic acid stearyl, isodecyl methacrylate, ethylhexyl methacrylate, ethyl triethylene glycol methacrylate, methoxy polyethylene glycol methacrylate-styrene polymer, butyldiglycol methacrylate and these compounds of ethoxylated fatty acid alcohol.Described have flexibility and give the content of monomer in macromolecule of function and can be preferably 3 weight %～15 weight %, more preferably 5 weight %～10 weight %.If described have flexibility and give the content of the monomer of function and surpass 15 weight %, then the phenomenon of peeling off of pattern becomes seriously in developing procedure, the deterioration of the rectilinear propagation of formed pattern.And less than 3 weight %, then high molecular glass transition temperature uprises as if this content, damages easily, and the flexibility of formed photosensitive polymer combination worsens.
And described other acrylic monomerss are used to regulate high molecular polarity.As the example of such acrylic monomers, can enumerate the potpourri of 2-hydroxyethyl ethyl (methyl) acrylate, (methyl) acrylic acid-2-hydroxyl monooctyl ester, (methyl) methyl acrylate, (methyl) ethyl acrylate, n-butyl acrylate and these compounds etc.Consider high molecular thermotolerance, dispersiveness, with the water wettability of developer solution etc., the content of such monomer in macromolecule is preferably 10 weight %～30 weight %.
Described acrylate polymeric resin can obtain by carry out polymerization in the solvent that can prevent the polarity that having of described 4 kinds of monomer gelations is suitable, the weight-average molecular weight of the acrylate resin of formed lower glass transition temperatures is preferably 10,000～35,000, more preferably about 20000.
In the photosensitive polymer combination of the present invention, described photopolymer resin (composition (A) (ii)) has been given play to the effect of the sensitivity that improves photosensitive polymer combination.Described photopolymer resin is the resin that is dissolved in alkaline aqueous solution, preferably represents with following Chemical formula 1 or Chemical formula 2,
[Chemical formula 1]
[Chemical formula 2]
In the above-mentioned formula,
R
1Be that hydrogen atom or carbon number are 1～2 alkyl independently of one another,
R
2Be that to have hydroxyl substituent or do not have substituent carbon number be 2～5 alkylidene,
A+b+c=1, and 0.1＜a＜0.4,0＜b＜0.5,0.1＜c＜0.6.
The weight-average molecular weight of described photopolymer resin can be preferably 10,000～80,000, and more preferably 15,000～50,000.The weight-average molecular weight of described photopolymer is in described scope the time, and removing at development time and residual film can be better aspect the degree.
General assembly (TW) with photosensitive polymer combination is a benchmark, the potpourri (being binder resin) of aforesaid epoxy resin and alkali soluble resins (acrylate resin and/or photopolymer resin) preferably uses with the amount of 1 weight %～50 weight %, the content of described binder resin is in described scope the time, have the photosensitive polymer combination that can obtain suitable viscosity, and the advantage of regulating thickness easily.
In the photosensitive polymer combination of the present invention, as described epoxy hardener (composition (B)), can use amine system, acid anhydrides system, imidazoles system, isocyanine system, mercaptan based compound etc., more particularly, can use amine compounds such as diethylene triamine (DETA), trien (TETA), triethylene five amine (TEPA), diaminodiphenyl-methane (DDM), diamino diphenyl sulfone (DDS), daiamid (polyamide amine), dicyandiamide; Polyamide; Acid anhydrides based compounds such as phthalic anhydride, trimellitic anhydride, pyromellitic acid dianhydride, maleic anhydride, tetrabydrophthalic anhydride, methyl tetrahydrophthalic anhydride, hexahydrophthalic anhydride, hydrogenated methyl phthalic anhydride; 2MZ (glyoxal ethyline), 2E4MZ imidazole compounds such as (2-ethyl-4-methylimidazoles); The isocyanine based compound; With mercaptan based compounds such as polymercaptan etc.
General assembly (TW) with composition is a benchmark, and described epoxy hardener preferably uses with the amount of 0.1 weight %～10 weight %.
At this moment, with respect to the epoxy radicals of 1 equivalent of epoxy resin, described epoxy hardener can be preferably with 0.5 equivalent～1.5 equivalents, further preferably use with the amount of 0.7 equivalent～1.2 equivalents.The content of described epoxy hardener can not obtain good degree of cure less than 0.5 equivalent or when surpassing 1.5 equivalents.
Can at random use curing accelerator as the reactive catalyzer that is used to promote epoxy hardener and epoxy resin according to the kind of employed epoxy hardener.As operable curing accelerator, can enumerate imidazoles such as glyoxal ethyline, 2-ethyl imidazol(e), 2-ethyl-4-methylimidazole; 2, phenols such as 4-xylenol; Phosphine classes such as triphenyl phasphine; Stannous octoate metallic compounds such as (オ Network チ Le acid ス ズ).With 100 weight portion epoxy resin is benchmark, and described curing accelerator can use with the amount of 0.1 weight portion～10 weight portions.
In the photosensitive polymer combination of the present invention, as described cross-linkable monomer (composition (C)) with alkene double bond, can use 1,4-butanediol diacrylate, 1,3 butyleneglycol diacrylate, glycol diacrylate, tetramethylol methane tetraacrylate, triethylene glycol diacrylate, polyethyleneglycol diacrylate, dipentaerythritol diacrylate, D-sorbite triacrylate, bisphenol a diacrylate derivant, TMPTA, dipentaerythritol polyacrylate; The methyl acrylic ester corresponding with above-mentioned acrylate; With potpourri of these compounds etc.
General assembly (TW) with photosensitive polymer combination is a benchmark, described cross-linkable monomer with alkene double bond can be preferably with 1 weight %～30 weight %, further preferably use with the amount of 3 weight %～20 weight %.The content of described cross-linkable monomer with alkene double bond can't be realized the flexibility of photosensitive polymer combination during less than 1 weight %, when this content surpasses 30 weight %, may reduce development and bonding force.
In the photosensitive polymer combination of the present invention, (composition (D)) can use all organic pigments or inorganic pigment as described pigment, as the concrete example of organic pigment, can enumerate the C.I. pigment yellow 83, C.I. pigment yellow 150, C.I. pigment yellow 13 8, C.I. pigment Yellow 12 8, C.I. pigment orange 43, C.I. paratonere 177, C.I. paratonere 202, C.I. paratonere 209, C.I. paratonere 254, C.I. paratonere 255, C.I. pigment Green 7, C.I. pigment green 36, C.I. pigment blue 15, C.I. pigment blue 15: 3, C.I. pigment blue 15: 4, C.I. pigment blue 15: 6, C.I. pigment Violet 23, C.I. pigment black 1, C.I. pigment black 7 etc.And, as the concrete example of inorganic pigment, can enumerate that titania, titanium are black, carbon black etc.These pigment also can mix more than one to be used to mix colours.
General assembly (TW) with photosensitive polymer combination is a benchmark, and described pigment can preferably use with the amount of 10 weight %～70 weight %.
In the photosensitive polymer combination of the present invention, described Photoepolymerizationinitiater initiater (composition (E)) plays the effect that causes the polymerization of described cross-linkable monomer under the effect of luminous ray, ultraviolet ray, far ultraviolet equiwavelength's light.As described Photoepolymerizationinitiater initiater, can use the potpourri of triazine based compound, diphenylhydroxyethanone based compound, acetophenone based compound, xanthone based compound, imidazole compound and these compounds etc., specifically, can use 2, two trichloromethyl-the 6-of 4-to methoxyl-styrene s-triazine, 2-to methoxyl-styrene-4, the two trichloromethyl s-triazine, 2 of 6-, 4-trichloromethyl s-triazine, 2,4-trichloromethyl-triazine based compounds such as 4-methyl naphthyl s-triazine; Benzophenone, to diphenylhydroxyethanone based compounds such as (diethylamino) benzophenone; 2,2-two chloro-4-metaphenoxy acetophenones, 2,2-diethoxy acetophenone, 2,2-dibutoxy acetophenone, 2-hydroxy-2-methyl propiophenone, to acetophenone based compounds such as tert-butyl group trichloroacetophenones; Xanthone, thioxanthones, 2-methyl thioxanthones, 2-isobutyl thioxanthones, 2-dodecyl thioxanthones, 2,4-dimethyl thioxanthones, 2, xanthone based compounds such as 4-diethyl thioxanthone; With 2, two (the 2-chlorphenyls)-4,5,4 of 2-, 5-tetraphenyl-1, the two imidazoles, 2 of 2-, two (2,4,6-tricyano phenyl)-4,4,5 of 2-, 5-tetraphenyl-1, imidazole compounds such as the two imidazoles of 2-etc.
General assembly (TW) with photosensitive polymer combination is a benchmark, described Photoepolymerizationinitiater initiater can be preferably with 0.3 weight %～5 weight %, further preferably use with the amount of 0.5 weight %～2 weight %.The content of described Photoepolymerizationinitiater initiater is during less than 0.3 weight %, exist degree of cure to reduce, cause being difficult to realize the problem that the rectilinear propagation of pattern, pattern of normal shape is also bad and so on because of muting sensitivity, when this content surpasses 5 weight %, aspect storage stability, have problems, may reduce owing to the degree of cure height causes resolution, the part that is easy to beyond the pattern that forms produces residue.
In the photosensitive polymer combination of the present invention, (composition (F)) can use in aspect The suitable solvent such as dissolubility and coatings as described solvent, concrete example as The suitable solvent, can enumerate propylene glycol monoethyl ether acetate, ethoxyl ethyl propionate, butyl acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol methyl ether acetate, diethylene glycol dimethyl ether, the diglycol ethyl methyl ether, cyclohexanone, 3-methoxy propyl acetoacetic ester, the potpourris of 3-ethoxy-propionic acid methyl esters and these compounds etc. especially preferably use propylene glycol monoethyl ether acetate, ethoxyl ethyl propionate or butyl acetate.
The content of described solvent is difference according to the difference of total solid component content in viscosity or the composition, the amount of the solvent that is contained is remaining residual amount behind the solid constituent that uses in removing photosensitive composite of the present invention, general assembly (TW) with photosensitive polymer combination is a benchmark, and the content of described solvent is preferably 5 weight %～60 weight %.Solvent is outside described scope the time, and the homogeneity that existence can't overcome thickness deviation, photosensitive polymer combination reduces such problem.
And, can also in photosensitive polymer combination of the present invention, further contain adjuvants such as surfactant, sensitizer, catalyzer as required.Particularly can use silicon system or fluorine is that surfactant is as described surfactant.
General assembly (TW) with photosensitive polymer combination is a benchmark, and the preferred amount of using 2 weight % at most of described adjuvant when this content surpasses 2 weight %, can produce residual film or stable the reduction.
According to other embodiments of the present invention, can provide by described photosensitive polymer combination being solidified the cured film that obtains, contain the color filter of described cured film and containing the flat-panel monitor of described color filter.
Use photosensitive polymer combination of the present invention, even adopt low-temperature setting operation below 200 ℃ also can access gas generated less, the cured film with reliability of thermotolerance and chemical resistance excellence.And, by utilizing described photosensitive polymer combination in alkaline aqueous solution, to develop, the cured film pattern that can access sensitivity and excellent in resolution, have excellent in shape can be at the industrial flat-panel monitor that the high color filter of reliability is provided effectively and contains this color filter.
Utilize following embodiment that the present invention is described in further detail below.But following embodiment only is used for the present invention is given an example, and scope of the present invention is not limited to these examples.In the following embodiments, unless specifically stated otherwise, percentage and mixing ratio all are benchmark with weight.
[embodiment]
(embodiment 1)
In the solvent of 35g propylene glycol methyl ether acetate (PGMEA), adding is as the 1g Irgacure 369 (Ciba manufacturing) and the 0.6g DETX-S (2 of Photoepolymerizationinitiater initiater, 4-diethyl-thioxanthones, Ciba is made), in stirring at normal temperature 30 minutes, after making the Photoepolymerizationinitiater initiater dissolving, add the DJB250 ((strain) east advance generation U.S. willing make) of 5g as the alkali solubility photopolymer resin, 2.5g NC-3000H (Nippon Kayaku K. K's manufacturing) as epoxy resin, 5g is as the DPHA (Japanese chemical drug (strain)) with cross-linkable monomer of alkene double bond, 0.7g MCD (Nippon Kayaku K. K's manufacturing) as epoxy hardener, in stirring at normal temperature after 1 hour, add the C.I. pigment blue 15 of 50g as pigment: 6 with the potpourri and the 0.2g adjuvant of C.I. pigment Violet 23, in stirring at normal temperature 1 hour.
With the composition that so obtains filter twice above to remove impurity, obtain photosensitive polymer combination of the present invention.
(embodiment 2)
Except using 50g C.I. paratonere 254, use the method acquisition photosensitive polymer combination identical with embodiment 1 as the pigment.
(embodiment 3)
Except using 45g C.I. pigment green 36 and 5g C.I. pigment yellow 13 8, use the method acquisition photosensitive polymer combination identical with embodiment 1 as the pigment.
(embodiment 4)
Except using 50g carbon black (20% solution), use the method acquisition photosensitive polymer combination identical with embodiment 1 as the pigment.
(embodiment 5)
Except using 5g to be used as the alkali soluble resins, use the method acquisition photosensitive polymer combination identical with embodiment 1 as the HIB of acrylate resin ((strain) east advance generation is beautiful agree make).
(embodiment 6)
Except mixing 2.5g uses as the HIB of acrylate resin ((strain) east advance generation is beautiful agree make) as the DJB250 of alkali-soluble photopolymer resin ((strain) east advance generation is beautiful agree make) and 2.5g, use the method acquisition photosensitive polymer combination identical with embodiment 1.
(comparative example 1)
Except not using epoxy resin and epoxy hardener, use the method acquisition photosensitive polymer combination identical with embodiment 1.
(comparative example 2)
Except not using epoxy resin and epoxy hardener, use the method acquisition photosensitive polymer combination identical with embodiment 5.
(comparative example 3)
Except not using the epoxy hardener, use the method acquisition photosensitive polymer combination identical with embodiment 1.
(comparative example 4)
Except not using the epoxy resin, use the method acquisition photosensitive polymer combination identical with embodiment 1.
The composition (g) of described embodiment 1～6 and comparative example 1～4 is listed in the table below 1.
[table 1]
Experimental example: the evaluation of physical property of cured film
The rerum natura of the cured film that the photosensitive polymer combination of being made by described embodiment 1～6 and comparative example 1～4 is obtained from gas generated, chemical resistance and stable on heating aspect is estimated.
At first,, make that coating thickness is 1 μ m～2 μ m, on 80 ℃ heating plate dry 2 minutes then, obtain coated film the photosensitive polymer combination rotary coating that produces.After placing photomask on the resulting coated film, utilize the ultrahigh pressure mercury lamp of the wavelength that sends 200nm～400nm to carry out the exposure of certain hour, make that exposure is that benchmark reaches about 100mJ/cm with 365nm
2, utilize KOH developer solution (DCD-260CF, (strain) east advance generation is beautiful agree make) to carry out the development of certain hour by spray nozzle after, under 150 ℃, 170 ℃, 190 ℃ and 230 ℃ of these 4 kinds of temperature, carry out 30 minutes after cure operation, produce cured film.
(1) gas generated mensuration
To cut off 10 with the size of 10mm * 70mm based on 4 kinds of test pieces of the temperature of curing behind above-mentioned the carrying out, put into JTD-505 automatic sampler (Autosampler) (Jai society), heating is 30 minutes under 240 ℃ vacuum condition, uses-40 ℃ condenser pipe to capture (collection) gas of emitting.By GC-MS it is separated, each material is carried out quantitative test.The results are shown in following table 2 with what so estimate.
Zero: gas generated with respect to the photosensitive polymer combination of producing less than 100%.
△: gas generated is 100%～200% with respect to the photosensitive polymer combination of producing.
*: gas generated photosensitive polymer combination with respect to production surpasses 200%.
[table 2]
(2) thermotolerance evaluation
4 kinds of test pieces based on the temperature of curing behind above-mentioned the carrying out are carried out 3 hours thermal treatment once more at 230 degree, the variation of pattern, the variation of colourity and the variation of thickness are estimated, it the results are shown in following table 3.
Zero: pattern does not change, and aberration (Δ Eab) is below 3.0.
△: pattern changes slightly, and aberration (Δ Eab) is 3.0～5.0.
*: change in pattern is more than 5.0 than big or aberration (Δ Eab).
※ change in pattern: occur crystalline polamer again on the patterned surfaces, the pattern bulging.
[table 3]
(3) chemical resistance evaluation
Will based on 4 kinds of test pieces of the temperature of curing behind above-mentioned the carrying out respectively in 5% HCl aqueous solution, 5% NaOH aqueous solution, NMP, dimethylbenzene, isopropyl alcohol dipping carry out drying after 60 minutes, the variation of pattern and the variation of colourity are estimated, and it the results are shown in following table 4.
And, the absorbance of the material of stripping in nmp solution is measured, the results are shown in Fig. 1.
Zero: pattern does not change, and aberration (Δ Eab) is below 3.0.
△: pattern changes slightly, and aberration (Δ Eab) is 3.0～5.0.
*: change in pattern is more than 5.0 than big or aberration (Δ Eab).
The ※ change in pattern: what pattern occurs peels off phenomenon, melting phenomenon, pattern bulging.
[table 4]
By the result of above-mentioned table 2～4 and Fig. 1 as can be known, compare with the situation of comparative example 1～4, the cured film that the resin combination of being made by embodiments of the invention 1～6 obtains also has low gas generated under the situation of having carried out curing under the low temperature below 200 ℃, has excellent thermotolerance and chemical resistance.
Claims (14)
1. photosensitive polymer combination, it is characterized in that, this photosensitive polymer combination contains: (A) as (i) epoxy resin of binder resin and (ii) alkali soluble resins, described alkali soluble resins is more than one the resin that is selected among the potpourri of acrylate resin, photopolymer resin and these resins; (B) epoxy hardener; (C) has the cross-linkable monomer of alkene double bond; (D) pigment; (E) Photoepolymerizationinitiater initiater; (F) solvent.
2. photosensitive polymer combination as claimed in claim 1, it is characterized in that, this photosensitive polymer combination contains: (A) of 1 weight %～50 weight % be as (i) epoxy resin of binder resin and (ii) alkali soluble resins, and described alkali soluble resins is more than one the resin that is selected among the potpourri of acrylate resin, photopolymer resin and these resins; 0.1 (B) epoxy hardener of weight %～10 weight %; 1 weight %～30 weight % (C) has the cross-linkable monomer of alkene double bond; (D) pigment of 10 weight %～70 weight %; 0.3 (E) Photoepolymerizationinitiater initiater of weight %～5 weight %; (F) solvent with 5 weight %～60 weight %.
3. photosensitive polymer combination as claimed in claim 1, it is characterized in that described epoxy resin is the resin that is selected among the potpourri of bisphenol A type epoxy resin, bisphenol f type epoxy resin, line style phenol aldehyde type epoxy resin, cresols line style phenol aldehyde type epoxy resin and these resins.
4. photosensitive polymer combination as claimed in claim 1 is characterized in that described acrylate resin has 10,000～35,000 weight-average molecular weight.
5. photosensitive polymer combination as claimed in claim 1 is characterized in that, described photopolymer resin represents with following Chemical formula 1 or Chemical formula 2,
[Chemical formula 1]
[Chemical formula 2]
In the above-mentioned formula,
R
1Be that hydrogen atom or carbon number are 1～2 alkyl independently of one another,
R
2Be that to have hydroxyl substituent or do not have substituent carbon number be 2～5 alkylidene,
A+b+c=1, and 0.1＜a＜0.4,0＜b＜0.5,0.1＜c＜0.6.
6. photosensitive polymer combination as claimed in claim 1 is characterized in that described photopolymer resin has 10,000～80,000 weight-average molecular weight.
7. photosensitive polymer combination as claimed in claim 1, it is characterized in that described epoxy hardener is the material that is selected among the potpourri of amine compound, acid anhydrides based compound, imidazole compound, isocyanine based compound, mercaptan based compound and these compounds.
8. photosensitive polymer combination as claimed in claim 1 is characterized in that, with respect to the epoxy radicals of 1 equivalent of epoxy resin, described composition contains the described epoxy hardener of 0.5 equivalent～1.5 equivalents.
9. photosensitive polymer combination as claimed in claim 1 is characterized in that, is benchmark with 100 weight portion epoxy resin, and described composition also contains the curing accelerator of 0.1 weight portion～10 weight portions.
10. photosensitive polymer combination as claimed in claim 9, it is characterized in that, described curing accelerator is to be selected from glyoxal ethyline, 2-ethyl imidazol(e), 2-ethyl-4-methylimidazole, 2, the material among the potpourri of 4-xylenol, triphenyl phasphine, stannous octoate and these compounds.
11. photosensitive polymer combination as claimed in claim 1, it is characterized in that, described cross-linkable monomer with alkene double bond is to be selected from 1, the 4-butanediol diacrylate, 1,3 butyleneglycol diacrylate, glycol diacrylate, tetramethylol methane tetraacrylate, triethylene glycol diacrylate, polyethyleneglycol diacrylate, the dipentaerythritol diacrylate, the D-sorbite triacrylate, the bisphenol a diacrylate derivant, TMPTA, the dipentaerythritol polyacrylate, material among the methyl acrylic ester corresponding and the potpourri of these compounds with the aforesaid propylene acid esters.
12. a cured film, it is cured and obtains each described photosensitive polymer combination in the claim 1～11.
13. a color filter, it contains the described cured film of claim 12.
14. a flat-panel monitor, it contains the described color filter of claim 13.
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| KR1020080019571A KR101464312B1 (en) | 2008-03-03 | 2008-03-03 | Photosensitive resin composition which is capable of being cured at a low temperature |
| KR1020080019571 | 2008-03-03 |
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Also Published As
| Publication number | Publication date |
|---|---|
| TW200947121A (en) | 2009-11-16 |
| KR101464312B1 (en) | 2014-11-21 |
| TWI461843B (en) | 2014-11-21 |
| KR20090094556A (en) | 2009-09-08 |
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