CN104345552A - Colored photosensitive resin composition, color filter, and liquid crystal display device having the same - Google Patents
Colored photosensitive resin composition, color filter, and liquid crystal display device having the same Download PDFInfo
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- CN104345552A CN104345552A CN201410317429.3A CN201410317429A CN104345552A CN 104345552 A CN104345552 A CN 104345552A CN 201410317429 A CN201410317429 A CN 201410317429A CN 104345552 A CN104345552 A CN 104345552A
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/1303—Apparatus specially adapted to the manufacture of LCDs
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- Optics & Photonics (AREA)
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- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
The invention relates to a colored photosensitive resin composition, a color filter, and a liquid crystal display device having the same. The colored photosensitive resin composition comprises coloring agent (A), binder resin (B), photo-polymerizing monomer (C), photo-initiator (D), antioxidant (E) and solvent (F), the coloring agent (A) comprises one or more dyes, the antioxidant (E) comprises a mixture of phenolic antioxidant and sulfur antioxidant, and the color filter is formed by using the colored photosensitive resin composition. The colored photosensitive resin composition has excellent heat resistance and provides high brightness.
Description
Technical field
The present invention relates to a kind of colored photosensitive resin composition, color filter and there is the liquid crystal indicator of this color filter.Specifically, the color filter the invention provides a kind of colored photosensitive resin composition, using said composition to be formed and the liquid crystal indicator with this color filter, described colored photosensitive resin composition has excellent thermotolerance, thus after making pyroprocess, color changes less and provides high brightness.
Background technology
Color filter has been widely used in imaging device and liquid crystal display (LCD), and its range of application is constantly expanded.Color filter is prepared conventionally by with under type: applied equably by the colored photosensitive resin composition comprising redness, green or blue pigment and be formed thereon on the black matrix substrate of black pattern, heat drying subsequently, obtained coated film is made to expose and develop, and heating and sclerosis further if desired, form the pixel of each color thus, and above operation is repeated to each color.
Colored photosensitive resin composition comprises pigment, adhesive resin, photopolymerization monomer and Photoepolymerizationinitiater initiater usually.In order to form black matrix", Photosensitve resin composition comprises black pigment.
No. 2009-0066076, korean patent application publication discloses a kind of color filter Photosensitve resin composition, and described composition comprises acryl adhesive resin, acrylic compounds carboxylate resin, photopolymerization monomer, Photoepolymerizationinitiater initiater, pigment, antioxidant and solvent containing double bond.Said composition uses the potpourri of the first antioxidant and the second antioxidant as antioxidant, described first antioxidant is selected from the group be made up of chinol class, amine, phenolic compound and composition thereof, described second antioxidant comprises phosphite (ester) compounds, prevents Photosensitve resin composition to be oxidized thus and strengthens its thermal stability.
But the brightness of the color filter prepared owing to using the Photosensitve resin composition only containing pigment is lower, therefore in order to highlight, studies the Photosensitve resin composition containing dyestuff.But, the composition containing dyestuff is difficult to the brightness desired by acquisition because thermotolerance is lower.
Summary of the invention
Technical matters
An object of the present invention is to provide a kind of colored photosensitive resin composition, described composition has excellent thermotolerance, thus after making pyroprocess, color changes less and provides high brightness.
Another object of the present invention is to provide a kind of color filter by using this colored photosensitive resin composition to be formed.
Another object of the present invention is to provide a kind of liquid crystal indicator with this color filter.
Technical scheme
According to an aspect of the present invention, provide a kind of colored photosensitive resin composition, described composition contains toner (A), adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D), antioxidant (E) and solvent (F), described colorant (A) comprises one or more dyestuffs, and described antioxidant (E) comprises the potpourri of phenol antioxidant and sulphur class antioxidant.
According to a further aspect in the invention, a kind of color filter by using this colored photosensitive resin composition to be formed is provided.
According to another aspect of the invention, a kind of liquid crystal indicator with this color filter is provided.
Advantageous effects
Colored photosensitive resin composition of the present invention uses the potpourri of phenol antioxidant and sulphur class antioxidant as antioxidant, and one or more dyestuffs that together use thermotolerance is lower are as colorant, improve thermotolerance thus and provide the color filter with high brightness.
Embodiment
In more detail the present invention will be described below.
An embodiment of the invention relate to a kind of colored photosensitive resin composition, described composition contains toner (A), adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D), antioxidant (E) and solvent (F), described colorant (A) comprises one or more dyestuffs, and described antioxidant (E) comprises the potpourri of phenol antioxidant and sulphur class antioxidant.
Colorant (A)
In an embodiment of the invention, the feature of colorant (A) is to comprise one or more dyestuffs, particularly orchil.
Dyestuff can be any one that this area is commonly used, such as, and cyanogen class, oxa anthracenes, azo, Anthraquinones, metal complex class, quinolines and pyrazoline ketone dyestuff.
Colorant (A) also can comprise one or more pigment together used with dyestuff.
Pigment can comprise the inorganic pigment (as metal oxide, metal complex and the inorganic salts comprising barium sulphate) and the organic pigment that are divided into pigment in Color Index (The Society of Dyers and Colourists).With regard to thermotolerance and colour rendering, preferably organic pigment.
As an example, the compound being divided into pigment in Color Index (The Society of Dyers and Colourists) can be but be not limited to the compound of following color index (C.I.) number.
C.I. pigment yellow 1,3,12,13,14,15,16,17,20,24,31,53,83,86,93,94,109,110,117,125,128,137,138,139,147,148,150,153,154,166,173,180,185,194 and 214;
C.I. pigment orange 13,31,38,40,42,43,51,55,59,61,64,65,71 and 73;
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,209,215,216,224,242,254,255,264 and 265.
With in paint, at least one in the group being selected from and being made up of C.I. pigment yellow 13 8, C.I. pigment yellow 13 9, C.I. pigment yellow 150, C.I. pigment yellow 185, C.I. paratonere 177, C.I. paratonere 242 and C.I. paratonere 254 preferably can be used.
Above-mentioned pigment can be used alone, or is used in combination.Such as, the potpourri of C.I. paratonere 254 and C.I. paratonere 177 can be preferably used to form red pixel.
Preferably, based on the total solids content of colored photosensitive resin composition of the present invention, with 5 % by weight ~ 70 % by weight, the amount that is more preferably 10 % by weight ~ 50 % by weight contains toner (A).
Preferably, based on the total solids content of colorant (A), with 0.5 % by weight ~ 100 % by weight, the amount that is more preferably 1 % by weight ~ 60 % by weight comprises dyestuff.When the amount of dyestuff is 1 % by weight ~ 60 % by weight, can high brightness be obtained, thus pattern can be formed fully and form the color filter pattern with high-quality.
Adhesive resin (B)
In an embodiment of the invention, adhesive resin (B) can be carboxyl group-containing monomer with can with the multipolymer of other monomers of described monomer copolymerization.
As an example, other can the monomer of copolymerization can be monomers containing carbon-to-carbon unsaturated bond, and described monomer comprises aromatic ethenyl compound, as styrene, α-methyl styrene, vinyltoluene etc.;
Unsaturated carboxylic ester compound, as methyl acrylate, methyl methacrylate, ethyl acrylate, β-dimethyl-aminoethylmethacrylate, butyl acrylate, butyl methacrylate, acrylic acid 2-hydroxy methacrylate, 2-hydroxyethyl methacrylate, benzyl acrylate, benzyl methacrylate etc.;
Undersaturated carboxylic acid amide's alkyl ester compound, as acrylate etc.;
Undersaturated carboxylic acid epihydric alcohol ester compound, as glycidyl methacrylate etc.;
Vinyl esters of carboxylic acids compound, as vinyl acetate, propionate etc.;
Vinyl cyanide compound, as vinyl cyanide, methacrylonitrile, α-chloro-acrylonitrile etc.;
Undersaturated oxetanes carbonate, as 3-methyl-acryloyloxy methy oxetane, 3-methyl-3-methacryloxymethyl oxetanes, 3-ethyl-3-acryloyloxymethyl oxetanes, 3-ethyl-3-methacryloxymethyl oxetanes, 3-methyl-3-acryloyl-oxyethyl oxetanes, 3-methyl-3-methacryloxyethyl oxetanes, 3-methyl-3-acryloyl-oxyethyl oxetanes, 3-methyl-3-methacryloxyethyl oxetanes etc.
Above-mentioned monomer may be used singly or two or more in combination.
The molecular weight distribution [weight-average molecular weight (Mw)/number-average molecular weight (Mn)] of adhesive resin (B) can be 1.5 ~ 6.0, be preferably 1.8 ~ 4.0.When the molecular weight distribution of adhesive resin is 1.5 ~ 6.0, developability can be improved.
Preferably, based on the total solids content of colored photosensitive resin composition, with 5 % by weight ~ 90 % by weight, the amount that is more preferably 10 % by weight ~ 70 % by weight comprises adhesive resin (B).When the amount of adhesive resin (B) is 5 % by weight ~ 90 % by weight, dissolubility in developing solution will become enough, thus make it be difficult to generate development residues on the substrate of non-pixellated part, and can prevent the film of pixelation part in exposure area from reducing in developing process, thus the good leakage of non-pixellated part can be obtained.
Photopolymerization monomer (C)
In an embodiment of the invention, photopolymerization monomer (C) for by Photoepolymerizationinitiater initiater through irradiate generate living radical or acid and polymerisable monomer.
The example of photopolymerization monomer can comprise ethylene glycol diacrylate, diacrylate triglycol ester, diacrylate 1, 4-butanediol ester, diacrylate 1, 6-hexanediol ester, diacrylic acid pentyl diol ester, acrylate, pentaerythritol, diacrylate pentaerythritol ester, pentaerythritol triacrylate, diacrylate dipentaerythritol ester, three acrylic acid dipentaerythritol ester, five acrylic acid dipentaerythritol ester, six acrylic acid dipentaerythritol ester, bisphenol a diacrylate, trimethylolpropane triacrylate, nobolak type epoxy base acrylate, Ethylene glycol dimethacrylate, diethyleneglycol dimethacrylate, TEGDMA, dimethyl allene acid propylene glycol ester, dimethacrylate 1, 4-butanediol ester, dimethacrylate 1, 6-hexanediol ester etc.
Preferably, based on the total solids content of colored photosensitive resin composition, with 5 % by weight ~ 45 % by weight, the amount that is more preferably 10 % by weight ~ 35 % by weight comprises photopolymerization monomer (C).When the amount of photopolymerization monomer (C) is 5 % by weight ~ 45 % by weight, intensity and the smoothness of pixel can be improved.
Photoepolymerizationinitiater initiater (D)
In an embodiment of the invention, Photoepolymerizationinitiater initiater (D) is unrestricted, as long as it can play the effect making adhesive resin (B) and photopolymerization monomer (C) be polymerized.Particularly, with regard to polymerization property, efficiency of initiation, absorbing wavelength, availability and price etc., Photoepolymerizationinitiater initiater can be selected from the group be made up of triazines, acetophenones, bisglyoxaline compounds, oxime compound and composition thereof.
The example of compound in triazine class can comprise 2, two (the trichloromethyl)-6-(4-methoxyphenyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl naphthyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-piperonyl-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl-styrene)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(5-methylfuran-2-base) vinyl]-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(furans-2-base) vinyl]-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(4-diethylamino-2-aminomethyl phenyl) vinyl]-1 of 4-, 3, 5-triazine and 2, two (trichloromethyl)-6-[2-(3 of 4-, 4-Dimethoxyphenyl) vinyl]-1, 3, 5-triazine.
The example of acetophenone compounds can comprise diethoxy acetophenone, 2-hydroxy-2-methyl-1-phenyl third-1-ketone, benzyl dimethyl ketal, 2-hydroxyl-1-[4-(2-hydroxyl-oxethyl) phenyl]-2-methyl-prop-1-ketone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-(4-methyl thio phenyl)-2-morpholinyl third-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) fourth-1-ketone, 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] the third-1-ketone and 2-(4-methyl-benzyl)-2-(dimethylamino)-1-(4-morpholino phenyl) fourth-1-ketone.
The example of bisglyoxaline compounds can comprise two (the 2-chlorphenyl)-4,4' of 2,2'-, 5,5'-tetraphenyl bisglyoxaline, 2,2'-two (2,3-dichlorophenyl)-4,4', 5,5'-tetraphenyl bisglyoxaline, 2,2'-two (2-chlorphenyls)-4,4', 5,5'-tetra-(alkoxyl phenyl) bisglyoxaline, 2,2'-two (2-chlorphenyls)-4,4', 5,5'-tetra-(tri-alkoxy phenyl) bisglyoxaline, 2, two (2, the 6-dichlorophenyl)-4,4 ' 5 of 2-, 5 '-tetraphenyl-1,2 '-bisglyoxaline, and wherein at 4,4', the phenyl of 5,5' position replaces the imidazoles having alkoxy carbonyl group.Wherein, preferably 2,2'-two (2-chlorphenyls)-4,4', 5,5'-tetraphenyl bisglyoxaline, 2, two (2, the 3-dichlorophenyl)-4,4' of 2'-, 5,5'-tetraphenyl bisglyoxaline and 2,2-two (2,6-dichlorophenyl)-4,4 ' 5,5 '-tetraphenyl-1,2 '-bisglyoxaline.
The example of oxime compound can comprise adjacent ethoxy carbonyl-α-oxyimino group-1-phenyl third-1-ketone, and the compound of formula (I) ~ (III):
In addition, when not damaging effect of the present invention, together can also use other Photoepolymerizationinitiater initiaters known in the art.Other Photoepolymerizationinitiater initiaters can be such as benzoin class, benzophenone, thioxanthene ketone, anthracene compounds, and it may be used singly or two or more in combination.
The example of benzoin compounds can comprise benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether.
The example of benzophenone compound can comprise benzophenone, o-benzoyl yl benzoic acid methyl esters, 4-phenyl benzophenone, 4-benzoyl-4'-methyldiphenyl thioether, 3; 3', 4,4'-tetra-(t-butyl peroxy carbonyl) benzophenone and 2; 4,6-tri-methyl benzophenone.
The example of thioxanthones compounds can comprise ITX, 2,4-diethyl thioxanthones, 2,4-bis-clopenthixal ketones and the chloro-4-propoxythioxanthone of 1-.
The example of anthracene compounds can comprise 9,10-dimethoxy anthracene, EDMO, 9,10-diethoxy anthracenes, 2-ethyl-9,10-diethoxy anthracene.
In addition, the example of other Photoepolymerizationinitiater initiaters can comprise TMDPO, 10-butyl-2-chloro-acridine ketone, 2-EAQ, 9,10-phenanthrenequione, camphorquinone, phenylglyoxalates methyl esters and two cyclopentadiene titanium compounds.
In addition, Photoepolymerizationinitiater initiater (D) can use together with light-initiated auxiliary agent (D-1).When Photoepolymerizationinitiater initiater (D) uses together with light-initiated auxiliary agent (D-1), colored photosensitive resin composition can have the susceptibility of enhancing, thus can improve throughput rate.
Specifically, light-initiated auxiliary agent (D-1) can be selected from the group be made up of amine, carboxylic acid, the organic compounds containing sulfur with mercapto and composition thereof.
The example of amine can comprise: fatty amine, as triethanolamine, methyldiethanolamine and triisopropanolamine; And aromatic amine, as 4-dimethylaminobenzoic acid methyl esters, EDMAB, 4-dimethylaminobenzoic acid isopentyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, benzoic acid 2-dimethylamino ethyl ester, N, N-dimethyl-p-toluidine, 4, two (dimethylamino) benzophenone (michaelis ketone) of 4'-and two (diethylamino) benzophenone of 4,4'-.Preferably aromatic amine.
Carboxylic acid can comprise aromatic series and to mix acetic acid, such as, phenyl acetic acid, aminomethyl phenyl thioacetic acid, ethylphenyl thioacetic acid, Methylethyl phenyl thioacetic acid, 3,5-dimethylphenyl thioacetic acid, methoxyphenylthio acetic acid, dimethoxyphenylthio acetic acid, chlorophenylthio acetic acid, dichlorophenyl thioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthio acetic acid, N-naphthyl glycocoll and naphthoxy acetic acid.
The example with the organic compounds containing sulfur of mercapto can comprise 2-mercaptobenzothiazole, 1, two (the 3-sulfydryl butyryl acyloxy) butane, 1 of 4-, 3,5-tri-(3-sulfydryl butoxyethyl group)-1,3,5-triazine-2,4,6 (1H, 3H, 5H)-triketone, three (3-mercaptopropionic acid) trihydroxy methyl propyl ester, four (3-mercaptobutyric acid) pentaerythritol ester, four (3-mercaptopropionic acid) pentaerythritol ester, six (3-mercaptopropionic acid) dipentaerythritol ester and two (3-mercaptopropionic acid) TEG ester.
Preferably, based on the total solids content of adhesive resin (B) and photopolymerization monomer (C), with 0.1 % by weight ~ 40 % by weight, the amount that is more preferably 1 % by weight ~ 30 % by weight comprises Photoepolymerizationinitiater initiater (D).When the amount of Photoepolymerizationinitiater initiater (D) is 0.1 % by weight ~ 40 % by weight, colored photosensitive resin composition of the present invention can have hypersensitivity thus shorten the time shutter, improves throughput rate thus, and keeps high resolving power.In addition, said composition can provide enough image pixel intensities and good Pixel surface flatness.
In addition, when using light-initiated auxiliary agent (D-1), preferably, based on the total solids content of adhesive resin (B) and photopolymerization monomer (C), with 0.1 % by weight ~ 50 % by weight, the amount that is more preferably 1 % by weight ~ 40 % by weight comprises light-initiated auxiliary agent (D-1).When the amount of light-initiated auxiliary agent is 0.1 % by weight ~ 50 % by weight, colored photosensitive resin composition of the present invention can have the susceptibility improved further, and improves the throughput rate of the color filter using said composition to be formed.
Antioxidant (E)
In an embodiment of the invention, antioxidant (E) comprises the potpourri of phenol antioxidant and sulphur class antioxidant.Compared with the independent a kind of antioxidant of use, use the potpourri of phenol antioxidant and sulphur class antioxidant can demonstrate the effect of improvement.
The example of phenol antioxidant can comprise 3, two [the 2-[3-(3-tertiary butyl-4-hydroxy-5-aminomethyl phenyl) propionyloxy]-1 of 9-, 1-dimethyl ethyl]-2, 4, 8, 10-tetra-oxaspiro [5.5] undecane (the ADEKASTAB AO-80 of ADEKA, the Sumilizer GA-80 of Sumitomo Chemical), four [3-(3, 5-di-tert-butyl-hydroxy phenyl) propionate (IRGANOX1010 of BASF, the ADEKASTAB AO-60 of ADEKA, the Sumilizer BP-101 of Sumitomo Chemical), 1, 3, 5-trimethyl-2, 4, 6-tri-(3 ' 5 '-di-tert-butyl-4-hydroxyl benzyl) benzene (IRGANOX1330 of BASF, the ADEKASTAB AO-330 of ADEKA), triethylene glycol-bis-[3-(the 3-tert-butyl group-5-methyl-4-hydroxy phenyl) propionic ester] (the ADEKASTAB AO-70 of IRGANOX245 and ADEKA of BASF), 4, 4 '-thiobis (the 6-tert-butyl group-3-methylphenol) (the Sumilizer WX of Sumitomo Chemical), three-(3, 5-di-tert-butyl-4-hydroxyl benzyl)-isocyanuric acid ester (IRGANOX3114 of BASF, the ADEKASTAB AO-20 of ADEKA), 1, 6-hexanediol-bis-[3-(3, 5-di-tert-butyl-hydroxy phenyl) propionic ester] (IRGANOX259 of BASF), 2, two [the 3-(3 of 2-thiodiethylene, 5-di-tert-butyl-hydroxy phenyl) propionic ester] (IRGANOX1035 of BASF), N, N '-hexa-methylene two (3, 5-di-t-butyl-4-hydroxy-hydrocineamide) (IRGANOX1098 of BASF), 2, two [(octylsulfo) the methyl]-orthoresol (IRGANOX1520L of BASF) of 4-, octadecyl-[3-(3, 5-di-tert-butyl-hydroxy phenyl) propionic ester (IRGANOX1076 of BASF, the ADEKASTAB AO-50 of ADEKA, the Sumilizer BP-76 of Sumitomo Chemical), 4, 4 '-butylidene-bis-(3 methy 6 tert butyl phenol) (ADEKASTAB AO-40 of ADEKA, the Sumilizer BBM of Sumitomo Chemical), 1, 1, 3-tri-(2-methyl-4-hydroxyl-5-tert-butyl-phenyl) butane (the ADEKASTAB AO-30 of ADEKA), 2, two (n-octylthio)-6-(the 4-hydroxyl-3 of 4-, 5-di-tert-butyl aniline)-1, 3, 5-triazine (IRGANOX565 of BASF), 4, two (the dodecylthiomethyl)-orthoresol (IRGANOX1726 of BASF) of 6-, the 2-tert-butyl group-6-(the 3-tert-butyl group-2-hydroxy-5-methyl base benzyl)-4-aminomethyl phenyl acrylate (the Sumilizer GM of Sumitomo Chemical), 2-[1-(2-hydroxyl-3, 5-di-tert-pentyl-phenyl) ethyl]-4, 6-di-tert-pentyl-phenyl acrylate (the Sumilizer GS of Sumitomo Chemical), mixed type 6-[3-(3-tertiary butyl-4-hydroxy-5-aminomethyl phenyl) propoxyl group]-2, 4, 8, 10-tetra-tert dibenzo [d, f] [1, 3, 2] dioxa hydrogen phosphide (dioxaphosphephine) (the Sumilizer GP of Sumitomo Chemical).
The example of sulphur class antioxidant can comprise 3, 3 '-thio-2 acid two (dodecyl) ester (the IRGANOX PS800FD of BASF), 3, 3 '-thio-2 acid two (octadecyl) ester (the IRGANOX PS802FD of BASF), thio-2 acid two (tridecyl) ester (the ADEKASTAB AO-503 of ADEKA), pentaerythrite four (β-lauryl thiopropionate) (the ADEKASTAB AO-412S of ADEKA), 3, 3 '-thiodipropionate dilauryl (the Sumilizer TPL-R of Sumitomo Chemical), 3, 3 '-thio-2 acid two myristin (the Sumilizer TPM of Sumitomo Chemical), 3, 3 '-thio-2 acid distearyl ester (the Sumilizer TPS of Sumitomo Chemical), pentaerythrite four (3-lauryl thiopropionate) (the Sumilizer TPD of Sumitomo Chemical), 3, 3 '-thio-2 acid two (tridecyl) ester (the Sumilizer TL of Sumitomo Chemical), 2-mercaptobenzimidazole (the Sumilizer MB of Sumitomo Chemical).
Colored photosensitive resin composition of the present invention uses the potpourri of phenol antioxidant and sulphur class antioxidant, thus improves thermotolerance and provide high brightness.
Preferably, based on the solids content of 100 weight portion Photoepolymerizationinitiater initiaters (D), antioxidant (E) is comprised with the amount of 5 weight portion ~ 75 weight portions.When the amount of antioxidant is 5 weight portion ~ 75 weight portion, can thermotolerance be improved and can high brightness be obtained.
Solvent (F)
In an embodiment of the invention, solvent (F) can be any solvent that can disperse or dissolve other components comprised in colored photosensitive resin composition of the present invention.Specifically, preferably ether, aromatic hydrocarbon, ketone, alcohol, ester and acid amides.
As an example, solvent (F) can comprise ethylene glycol monoalkyl ether, as ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol list propyl ether and ethylene glycol monobutyl ether;
Diethylene glycol dialkyl ether, as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether and diethylene glycol dibutyl ether;
Ethylene glycol alkylether acetates, as methylcellosolve acetate and ethyl cellosolve acetate;
Alkylene glycol alkyl ether acetic acid esters, as propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, propylene glycol monopropyl ether acetic acid esters, methoxybutyl acetic acid esters and methoxyphenyl acetate;
Aromatic hydrocarbon, as benzene,toluene,xylene and trimethylbenzene;
Ketone, as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone;
Alcohol, as ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol and glycerine; With
Ester, as 3-ethoxyl ethyl propionate, 3-methoxy methyl propionate, and cyclic ester, as gamma-butyrolacton.
With regard to coating and drying, solvent (F) can be preferably the organic solvent that boiling point is 100 DEG C ~ 200 DEG C, be more preferably alkylene glycol alkyl ether acetic acid esters, ketone and ester, as 3-ethoxyl ethyl propionate and 3-methoxy methyl propionate, and then be more preferably propylene glycol methyl ether acetate, propylene glycol monoethyl acetic acid esters, cyclohexanone, 3-ethoxyl ethyl propionate and 3-methoxy methyl propionate.Above-mentioned solvent can be used alone, or is used in combination.
Preferably, based on the gross weight of colored photosensitive resin composition of the present invention, with 60 % by weight ~ 90 % by weight, the amount that is more preferably 70 % by weight ~ 85 % by weight comprises solvent (F).When the amount of solvent (F) is 60 % by weight ~ 90 % by weight, utilize as roll coater, spin coater, slit spin coater, slit are coated with the coating machines such as machine (also referred to as " mould painting machine ") and ink jet printer and can obtain good coating.
If desired, the colored photosensitive resin composition of an embodiment of the invention also can comprise other polymkeric substance, rigidizer, surfactant, adhesion promotor, UV absorbing agent, anti-coalescer etc.
The example of other polymkeric substance can comprise: curable resin, as epoxy resin and maleimide resin; And thermoplastic resin, as polyvinyl alcohol (PVA), polyacrylic acid, polyalkylene glycol monoalkyl ether, polyacrylic acid fluoroalkyl ester, polyester and polyurethane.
Rigidizer is for strengthening depth-hardened and physical strength.The example of rigidizer can comprise epoxy compound (epoxies), multi-functional isocyanates, melamine and oxetanes.
The example of epoxy compound comprises the brominated derivative of bisphenol A type epoxy resin, bisphenol-A epoxy resin, bisphenol f type epoxy resin, A Hydrogenated Bisphenol A F type epoxy resin, phenolic resin varnish type epoxy resin, other aromatic epoxy resins, acrylic compounds epoxy resin, glycidyl ester resin, glycidyl amine resins, these epoxy resin; Be different from the aliphatics of these epoxy resin and brominated derivative, alicyclic or aromatic epoxy compound; Epoxy butadiene (being total to) polymkeric substance; Epoxy isoprene (being total to) polymkeric substance; (methyl) glycidyl alcohol ester (being total to) polymkeric substance; With isocyanuric acid three-glycidyl alcohol ester.
The example of oxetanes can comprise carbonic acid dioxygen azetidine, dimethylbenzene dioxygen azetidine, hexane diacid dioxygen azetidine, terephthalic acid (TPA) dioxygen azetidine and cyclohexane dicarboxylic acid dioxygen azetidine.
Rigidizer can with can bring out epoxy compound or oxetanes ring-opening polymerization stiffening aids together with use.The example of stiffening aids can comprise polybasic carboxylic acid, polybasic acid anhydride and acid agent.
Polybasic acid anhydride can be epoxy resin hardener commercially available prod, such as, and ADEKAHADONA EH-700 (ADK Industries), RIKACID HH (NJC) and MH-700 (NJC).
Above-mentioned rigidizer can be used alone, or is used in combination.
Surfactant for strengthening the coating formation character of colored photosensitive resin composition of the present invention, and can comprise fluorine and silicon class surfactant.
The example of silicon class surfactant can comprise commercially available prod, as DC3PA, DC7PA, SH11PA, SH21PA and SH8400 (Dow Corning Toray Silicone), and TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460 and TSF-4452 (GE Toshiba Silicones).The example of fluorine class surfactant can comprise commercially available prod, as MEGAFACE F-470, F-471, F-475, F-482 and F-489 (Dainippon Ink and Chemical Industry).
Above-mentioned surfactant can be used alone, or is used in combination.
The example of adhesion promotor can comprise vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-amino propyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330, APTES, 3-glycidoxypropyltrimewasxysilane, 3-glycidoxypropyl dimethoxysilane, 2-(3, 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-methacryloxypropyl trimethoxy silane, 3-mercaptopropyi trimethoxy silane, 3-isocyanates propyl trimethoxy silicane and 3-isocyanates propyl-triethoxysilicane.
Above-mentioned adhesion promotor can be used alone, or is used in combination.Preferably, based on the total solids content of Photosensitve resin composition of the present invention, with 0.01 % by weight ~ 10 % by weight, the amount that is more preferably 0.05 % by weight ~ 2 % by weight comprises adhesion promotor.
The example of UV absorbing agent can comprise 2-(the 3-tert-butyl group-2-hydroxy-5-methyl base phenyl)-5-chlorobenzotriazole and alkoxy benzophenone.
The example of anti-coalescer can comprise sodium polyacrylate.
The colored photosensitive resin composition of one embodiment of the present invention can be prepared by the following method.Such as, colorant (A) is mixed with solvent (F), and utilize ball mill to be disperseed by this potpourri, until the mean diameter of colorant reaches less than about 0.2 μm.If desired, hybrid pigment spreading agent or partly or entirely adhesive resin (B).Remaining adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D) and other components is added in the dispersion (also referred to as " powder base (mill base) ") of mixing, if desired, solvent can be added further to obtain desired concentration, thus prepare colored photosensitive resin composition.
An embodiment of the invention relate to the color filter by using above-mentioned colored photosensitive resin composition to be formed.The color filter of one embodiment of the present invention comprises the dyed layer formed in the following manner: be coated in by colored photosensitive resin composition on substrate, develops with post-exposure, thus forms pattern.
The method using colored photosensitive resin composition of the present invention to form pattern will be described in detail below.
The method using colored photosensitive resin composition of the present invention to form pattern can be undertaken by means known in the art, and generally includes coating, exposure and removal step.Colored photosensitive resin composition of the present invention is coated on substrate, carries out photocuring subsequently and develop, to form the pattern as black matrix" or colour element (coloured image).
In coating step, (this area routine uses colored photosensitive resin composition of the present invention to be coated in substrate, such as, glass or silicon wafer, unrestricted) on the pre-formed layer of upper or colored photosensitive resin composition, carry out predrying to remove as volatile constituents such as solvents subsequently, thus level and smooth coated film is provided.Coated film preferably has the thickness of 1 μm ~ 3 μm.
In step of exposure, in order to obtain desired pattern, UV is used to irradiate the specific region of coated film use mask.For utilizing parallel rays uniform irradiation Zone Full and making mask align substrates exactly, preferably use mask aligner or ledex.
In removal step, with aqueous alkali, the coated film of being irradiated solidification by UV is contacted that unexposed area is dissolved develop, obtain desired pattern thus.After development, drying can be carried out 10 minutes ~ 60 minutes at 150 DEG C ~ 230 DEG C if desired.
Any developing solution known in the art can be used to develop.Specifically, the aqueous solution containing alkali cpd and surfactant can be used.
Alkali compounds can be inorganic or organic basic compound.The example of inorganic alkaline compound can comprise NaOH, potassium hydroxide, sodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate (ADP), potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, sal tartari, sodium bicarbonate, saleratus, sodium borate, potassium borate and ammoniacal liquor.The example of organic basic compound can comprise Tetramethylammonium hydroxide, 2-hydroxyethyl trimethylammonium hydroxide, monomethyl amine, dimethyl amine, Trimethylamine, MEA, diethylamide, triethylamine, single isopropylamine, diisopropylamine and monoethanolamine.These inorganic and organic basic compounds can be used alone, or are used in combination.Based on the gross weight of developing solution, alkali compounds can be comprised with 0.01 weight portion ~ 10 weight portion, the preferably amount of 0.03 weight portion ~ 5 weight portion.
Surfactant can be nonionic, anionic or cationic surfactant.The example of non-ionics can comprise polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkylaryl ether and other polyoxyethylene derivs, POLOXAMER, sorbitan aliphatic ester, Polyoxyethylene Sorbitan acid esters, polyoxyethylene sorbitol fatty acid ester, fatty acid glyceride, polyoxyethylene fatty acid ester and polyoxyethylene alkyl amine.The example of anionic surface active agent can comprise: higher alcohol sulfate, as sldium lauryl sulfate and oleyl alcohol sodium sulphate; Alkyl sulfate, as NaLS and Texapon Special; Alkyl aryl sulfonate, as neopelex and dodecyl sodium naphthalene sulfonate.The example of cationic surfactant can comprise amine and quaternary ammonium salt, as stearic amine hydrochloride and lauryl trimethyl ammonium chloride.These surfactants can be used alone, and also can be used in combination.Based on the gross weight of developing solution, surfactant can be comprised with the amount being preferably 0.01 weight portion ~ 10 weight portion, being more preferably 0.05 weight portion ~ 8 weight portion and then being more preferably 0.1 weight portion ~ 5 weight portion.
As mentioned above, colored photosensitive resin composition carries out applying, dry, exposing patterns and development, the pixel corresponding with each color of coloured material in Photosensitve resin composition or black matrix" are provided thus, and the number of colors needed for color filter repeats these operations, obtains color filter thus.The formation of color filter and preparation are known in the art, and thus omit it at this and describe in detail.
An embodiment of the invention relate to a kind of liquid crystal indicator with above-mentioned color filter.
Liquid crystal indicator of the present invention has above-mentioned color filter, and comprises other assemblies as known in the art.Namely, present invention encompasses any liquid crystal indicator that can adopt color filter of the present invention.Such as transmissive liquid crystal display device, the comparative electrode substrate wherein with thin film transistor (TFT) (TFT), pixel electrode and both alignment layers is facing with each other with predetermined space, and in this interval, introduces liquid crystal material to form liquid crystal layer.In addition, can mention reflection-type liquid-crystal display device, described device has reflection horizon between colour filtering chip basic board and dyed layer.In addition, can also mention following liquid crystal indicator, described device comprises thin film transistor (TFT) (TFT) substrate be combined in the transparency electrode of color filter and the backlight be fixed on the TFT substrate position overlapping with color filter.
Further illustrate the present invention by following examples, comparative example and experimental example, and should not think that they limit the scope of the invention.
Embodiment 1 ~ 2 and comparative example 1 ~ 4: the preparation of colored photosensitive resin composition
By mixing each component (unit: % by weight) prepare colored photosensitive resin composition with ratio listed in following table.
[table 1]
Each component of upper table 1 is as follows.
Colorant (A)
A-1:C.I. paratonere 254
A-2: red 94 (TCI) of acid
Adhesive resin (B)
B-1: the copolymerization (mol ratio of methacrylic acid unit and benzyl methacrylate unit: 31:69 of methacrylic acid and benzyl methacrylate; Acid number: 105; Weight-average molecular weight: 30,000)
Photopolymerization monomer (C)
C-1: six acrylic acid dipentaerythritol ester (KAYARAD DPHA, Nippon Kayaku)
Photoepolymerizationinitiater initiater (D)
D-1：OXE-01(Ciba)
Antioxidant (E)
E-1: phenol antioxidant AO-60 (ADEKA)
E-2: sulphur class antioxidant AO-412S (ADEKA)
E-3: sulphur class antioxidant AO-503 (ADAKA)
E-4: mixed type inhibitors Sumilizer GP (Sumitomo Chemical)
Solvent (F)
F-1: propylene glycol monomethyl ether
F-2:3-ethoxyl ethyl propionate
Adjuvant (G)
G-1: silicon class surfactant (SH-8400)
G-2: pigment dispersing agent
G-3: adhesion promotor (3-methacryloxypropyl trimethoxy silane)
Experimental example 1: the evaluation of brightness and thermotolerance
The colored photosensitive resin composition of preparation in embodiment 1 and 2 and comparative example 1 ~ 4 is used to prepare color filter.Specifically, each colored photosensitive resin composition is applied on the glass substrate by spin coating, and glass substrate is placed the temperature 3 minutes keeping 100 DEG C on hot plate, to form film on the glass substrate.Subsequently, will there is the line/intermittent pattern of 1 μm ~ 50 μm and the test light mask of the pattern of transmittance stepped change in 1% ~ 100% scope is placed on film, and use 1KW high-pressure sodium lamp with 100mJ/cm under without any special optical filter
2between film and photomask be spaced apart 100 μm under carry out UV irradiation, described mercury lamp contains whole g, h and i ray.The film that irradiates through UV to be immersed in KOH (pH10.5) aqueous solution being used as developing solution 2 minutes.After development, film washed with distilled water and uses nitrogen drying, being set to heat 1 hour in the baking oven of 220 DEG C, to provide color filter subsequently.The color filter obtained is through confirming that thickness is 2.0 μm.
As above the color filter prepared utilizes following methods to evaluate its brightness and thermotolerance.Result display in table 2.
(1) brightness (Y)
Microspectrophotometer OSP-SP2000 is used to measure brightness and the chromaticity coordinates of dyed layer.
O: be greater than 17.8, △: 17.6 ~ 17.8, X: be less than 17.6
(2) thermotolerance
By color filter being set to heat after 2 hours in the baking oven of 230 DEG C, measure color change (△ Eab), and confirm brightness change (△ Y).
△Eab
O: be less than 3, △: 3 ~ 4, X: be greater than 4
△Y
O: be less than 0.3, △: 0.3 ~ 0.5, X: be greater than 0.5
[table 2]
(standard Rx=0.656, Ry=0.323)
As shown in table 2, with use phenol antioxidant or sulphur class antioxidant comparative example 1 ~ 4 colored photosensitive resin composition compared with, use the colored photosensitive resin composition of the present invention of the potpourri of phenol antioxidant and sulphur class antioxidant to have excellent thermotolerance, and after heating in addition, demonstrate less brightness change and higher brightness.
Although shown and described particular implementation of the present invention, but it will be appreciated by those skilled in the art that, it is not intended to make the present invention be limited to these preferred implementations, and it will be apparent to one skilled in the art that, can make various changes and modifications, and not depart from the spirit and scope of the invention.
Therefore, scope of the present invention will by claims and equivalents thereof.
Claims (8)
1. a colored photosensitive resin composition, described colored photosensitive resin composition contains toner (A), adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D), antioxidant (E) and solvent (F), described colorant (A) comprises one or more dyestuffs, and described antioxidant (E) comprises the potpourri of phenol antioxidant and sulphur class antioxidant.
2. colored photosensitive resin composition as claimed in claim 1, wherein, described colorant (A) comprises one or more orchils.
3. colored photosensitive resin composition as claimed in claim 1, wherein, described colorant (A) also comprises pigment.
4. colored photosensitive resin composition as claimed in claim 1, wherein, based on the total solids content of described colored photosensitive resin composition, the amount with 5 % by weight ~ 70 % by weight contains described colorant (A).
5. colored photosensitive resin composition as claimed in claim 4, wherein, based on the total solids content of described colorant (A), contains described dyestuff with the amount of 1 % by weight ~ 60 % by weight.
6. colored photosensitive resin composition as claimed in claim 1, wherein, based on the solids content of Photoepolymerizationinitiater initiater (D) described in 100 weight portions, contains described antioxidant (E) with the amount of 5 weight portion ~ 75 weight portions.
7. a color filter, described color filter is formed by using the colored photosensitive resin composition according to any one of claim 1 ~ 6.
8. a liquid crystal indicator, described device has color filter according to claim 7.
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| KR1020130090640A KR102047371B1 (en) | 2013-07-31 | 2013-07-31 | Colored Photosensitive Resin Composition, Color Filter, and Liquid Crystal Display Device Having the Same |
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| CN109426075A (en) * | 2017-08-23 | 2019-03-05 | 东友精细化工有限公司 | Colored curable resin composition, colour filter and display device |
| JP2021177243A (en) * | 2017-03-07 | 2021-11-11 | 富士フイルム株式会社 | Laminate, optical filter, solid state imaging device, image display device, infrared sensor and kit |
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| KR102299970B1 (en) * | 2015-03-27 | 2021-09-08 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| KR102186496B1 (en) * | 2015-03-27 | 2020-12-03 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| KR102288719B1 (en) * | 2015-03-27 | 2021-08-11 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| KR102361511B1 (en) * | 2015-12-18 | 2022-02-10 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter and image display device using the same |
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| TW201510655A (en) | 2015-03-16 |
| KR20150015098A (en) | 2015-02-10 |
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| KR102047371B1 (en) | 2019-11-21 |
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