CN103969949A - Colored Photosensitive Resin Composition - Google Patents

Colored Photosensitive Resin Composition Download PDF

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Publication number
CN103969949A
CN103969949A CN201410042815.6A CN201410042815A CN103969949A CN 103969949 A CN103969949 A CN 103969949A CN 201410042815 A CN201410042815 A CN 201410042815A CN 103969949 A CN103969949 A CN 103969949A
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Prior art keywords
compound
antioxidant
methyl
weight
acid
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Granted
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CN201410042815.6A
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CN103969949B (en
Inventor
安大熙
申泳璨
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • 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
    • 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
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials For Photolithography (AREA)

Abstract

The invention discloses a colored photosensitive resin composition including a red coloring agent, an alkali soluble resin, photopolymerisable compound, a polymerization trigger and a solvent. The alkali soluble resin has an acid value of 30mg KOH/g TO 170mg KOH/g. The antioxidant includes antioxidant functional group based on phenol and antioxidant functional group based on phosphor or antioxidant functional group based on phenol and the antioxidant functional group based on sulphur. The polymerization trigger includes compound indicated by a formula 1. Since the composition has high developing rate and excellent photosensitivity and bonding performance, so that pattern layering can be inhibited in a developing process. Therefore, a color filter made from the photopolymerisable compound can have extremely high comparison and light transmittence.

Description

Photosensitive composition
Technical field
The present invention relates to a kind of photosensitive composition.
Background technology
Color filter is widely used in imaging device, for example, and so-called charge-coupled device (CCD), liquid crystal display (LCD) etc., and expanded rapidly the range of application of color filter.In color LCD or CCD, color filter used is conventionally by the technique below repeating and manufactured, this technique comprises: equably apply photosensitive composition to having on the substrate of black matrix" of patterning thereon, said composition comprises and corresponds respectively to redness, green and blue pigment; Heating and dry (being often called as " precalcining ") this substrate, to form film; By this film exposure and development; With about every kind of color, selectively further heating and solidifying (being often called as " calcining afterwards "), to form versicolor pixel.
In recent years, due to widening of improvement in quality of CCD or LCD and purposes, extremely need display panel significantly to improve brightness.For this reason, in different directions, carried out increasing the research of the brightness (Y value) of blue, red or green coloring photosensitive combination.
At present, in color filter, be mainly used in the paratonere 177(PR177 of redness (R) pixel) and paratonere 254(PR254) combined colors material present high contrast, but there is low brightness (Y value).Therefore, if use the color filter with three looks (R, G, B), compare with blue pixel with green pixel, the aforementioned red pixel that contains combined colors material can have relatively low brightness.Therefore,, in the time that color filter is used in liquid crystal display, should use the backlight of high output according to the brightness of red pixel, to realize sufficient color rendering, contrast and sharpness on coloured image.
Korean patent application publication No.2012-112188 discloses a kind of red composition for color filter, and comprises the color filter of said composition, but it does not propose to overcome any alternative scheme of foregoing problems.
Summary of the invention
Therefore, the object of this invention is to provide a kind of photosensitive composition that there is less change color and have simultaneously the color filter of excellent transmittance that is used to form.
Another object of the present invention is to provide a kind of have high developing powder and the light sensitivity of excellence and the photosensitive composition of viscosity, there is not the layering of pattern in developing process.
Another object of the present invention is to provide a kind of photosensitive composition that is used to form the color filter with high brightness and contrast.
Above-mentioned purpose of the present invention realizes by following feature:
(1) photosensitive composition, comprising: red stain, alkali soluble resins, photopolymerization compound, antioxidant, Photoepolymerizationinitiater initiater and solvent, and wherein, described alkali soluble resins has the acid number of 30mgKOH/g to 170mg KOH/g; Described antioxidant comprises the antioxidant functional group based on phenol and the antioxidant functional group based on phosphorus or the antioxidant functional group based on phenol and the antioxidant functional group based on sulphur; Described Photoepolymerizationinitiater initiater comprises the compound being represented by following formula 1:
[formula 1]
Wherein R 1expression-R 4-R 5; R 2and R 3respectively to there is 1 alkyl to 8 carbon atoms, phenyl, benzyl or diphenyl sulfide based, described alkyl, phenyl, benzyl or diphenyl sulfide based be unsubstituted or by hydroxyl or there is 1 alkyl to 8 carbon atoms and replace; R 4to there is 1 alkylidene to 4 carbon atoms; And R 5to there are 3 naphthenic base to 8 carbon atoms.
(2) according to the composition above-mentioned (1) Suo Shu, wherein, described alkali soluble resins has the acid number of 50mg KOH/g to 160mg KOH/g.
(3) according to the composition above-mentioned (1) Suo Shu, wherein, described antioxidant is selected from 3,5-bis--tertiary butyl-4-hydroxy benzyl phosphoric acid, 6-[3-(3-tertiary butyl-4-hydroxy-5-methyl) propoxyl group]-2,4,8,10-tetra--tert-butyl group dibenzo [d, f] [1,3,2]-dioxy phosphorus heterocycle heptane (dioxaphosphepine), sulfo-diethylene two [3-(3,5-bis--tert-butyl-hydroxy phenyls) propionic ester], 2, at least one in 2 '-thiobis (6-tert-butyl-4-methyl-Phenol) and 2,4-bis-(dodecyl sulfidomethyl)-6-methylphenol.
(4) according to the composition above-mentioned (1) Suo Shu, wherein, according to solids content, for the general assembly (TW) of described photosensitive composition, the amount of the described red stain comprising is that 5 % by weight (percentage by weight) are to 60 % by weight, the amount of the described alkali soluble resins comprising is 10 % by weight to 80 % by weight, and the amount of the described photopolymerization compound comprising is 5 % by weight to 45 % by weight; According to solids content, the amount of the described Photoepolymerizationinitiater initiater comprising accounts for 0.1 % by weight to 40 % by weight of the content sum of described alkali soluble resins and described photopolymerization compound; The amount of the described antioxidant comprising accounts for 1 % by weight to 100 % by weight of described Photoepolymerizationinitiater initiater content; And the amount of the described solvent comprising accounts for 60 % by weight to 90 % by weight of the general assembly (TW) of described photosensitive composition.
(5), according to the composition above-mentioned (1) Suo Shu, wherein, the amount of the described compound that the through type 1 comprising represents accounts for 10 % by weight to 100 % by weight of the general assembly (TW) of described Photoepolymerizationinitiater initiater.
(6) according to the composition above-mentioned (1) Suo Shu, also comprise at least one Photoepolymerizationinitiater initiater being selected from aceotphenone compound, benzophenone cpd, triaizine compounds, united imidazole and thioxanthones compound.
(7), according to the composition above-mentioned (1) Suo Shu, also comprise that at least one photopolymerization in the organosulfur compound that is selected from amines, carboxylic acid compound and contain sulfydryl causes reinforcing agent.
(8) a kind of color filter of making according to the photosensitive composition described in any one in above-mentioned (1) to (7) that uses.
(9) liquid crystal display, comprises according to the color filter above-mentioned (8) Suo Shu.
Use the color filter of photosensitive composition manufacturing of the present invention to there is high brightness and contrast and there is a less change color, obtain thus excellent transmittance.
Can allow rapid development and there is excellent cohesive according to photosensitive composition of the present invention, thereby during developing process, suppressing pattern layering.
Embodiment
The invention discloses a kind of photosensitive composition, described composition comprises: red stain, alkali soluble resins, photopolymerization compound, antioxidant, Photoepolymerizationinitiater initiater and solvent, wherein, described alkali soluble resins has the acid number of 30mg KOH/g to 170mg KOH/g; Described antioxidant comprises the antioxidant functional group based on phenol and the antioxidant functional group based on phosphorus or the antioxidant functional group based on phenol and the antioxidant functional group based on sulphur; Described Photoepolymerizationinitiater initiater comprises the compound being represented by formula 1, said composition can have high developing powder and excellent light sensitivity and cohesive thus, to suppress pattern layering in developing process, and, use the color filter of above-mentioned composition manufacturing can there is excellent high brightness and contrast.
Hereinafter, the present invention will be described in further detail.
Can comprise red stain, alkali soluble resins, photopolymerization compound, antioxidant, Photoepolymerizationinitiater initiater and solvent according to photosensitive composition of the present invention.
< red stain >
According to the present invention, redness is the adopted name of red serial color instead of unique a kind of color with particular color index.
Can comprise pigment and dyestuff according to red stain of the present invention.
Pigment used can be included in arbitrary organic pigment, inorganic pigment or its potpourri conventional in correlation technique in the present invention.
Organic pigment is not particularly limited, but can comprise, for marking ink, any universal pigment of ink-jet ink etc., more specifically, water-soluble azo pigment, water-fast AZO pigments, phthalocyanine color, quinacridone pigment, isoindolinone pigment, isoindoline pigment, perylene pigment, purple cyclic ketones pigment, dioxazines pigment, anthraquinone pigment, dianthraquinone pigment, anthrapyrimidine pigment, anthanthrone pigment, indanthrone pigment, yellow scholar's ketone pigment, pyranthrone pigments, pyrrolo-pyrrole-dione pigment etc., these pigment can use separately or with two or more be used in combination wherein.
Inorganic pigment is not particularly limited, but (for example can comprise metallic compound, metal oxide or metal complex) and carbon black, more specifically, the oxide of at least one metal in chosen from Fe, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, it can use separately or with two or more be used in combination wherein.
Organic pigment and inorganic pigment can comprise according to the compound of the pigment of colour index (Color Index is announced by dyeing association of man of Britain (Society of Dyers and Colorists)) classification.More specifically, can use C.I. pigment yellow 13,20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,148,150,153,154,166,173,180 and 185; C.I. pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65 and 71; C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,208,215,216,224,242,254,255 and 264 etc.Preferably, can use C.I. pigment yellow 13 8,139,150 and 185; C.I. pigment orange 38; C.I. pigment red 122,166,177,208,242,254 and 255 etc.These materials can use separately or with two or more be used in combination wherein.
Need only dye soluble in organic solvent, and can ensure that dyestuff is not particularly limited, for example, can comprise: the acid dyes with acidic group (as sulfonic acid, carboxylic acid etc.) as the reliability of the dissolubility in alkaline-based developer, thermotolerance, solvent resistance etc.; The salt of nitrogen-containing compound and acid dyes; The sulfonamide of acid dyes and its derivant; The acid dyes of azo-based, xanthene and/or phthalocyanine and their derivant etc.
Dyestuff preferably includes and is classified as according to the dyestuff of colour index (being announced by dyeing man association of Britain (Society ofDyers and Colorists)) or in The Dye Note(Color Dyeing company) in the compound of orchil, blue dyes and cudbear in the dyestuff listed.
Dyestuff is not particularly limited, but can comprise, for example, C.I. solvent dye (for example, C.I. solvent red 8,45,49,89,111,122,130,132,146,179 etc.) and in organic solvent, have excellent solubility aspect, C.I. solvent red 8,49,89,111,122,132,146 and 179 is preferred, more preferably, uses C.I. solvent red 8,122 and 132.
In addition, C.I. direct dyes can comprise, for example, C.I. directly red 79,82,83,84,91,92,96,97,98,99,105,106,107,172,173,176,177,179,181,182,184,204,207,211,213,218,220,221,222,232,233,234,241,243,246,250 etc.
In addition, C.I. mordant dye can comprise, for example, C.I. mordant rouge 1,2,3,4,9,11,12,14,17,18,19,22,23,24,25,26,30,32,33,36,37,38,39,41,43,45,46,48,53,56,63,71,74,85,86,88,90,94,95 etc.
These dyestuffs can use separately or with two or more be used in combination wherein.
The content of dyestuff is not particularly limited, and still, for example, according to solids content, for the general assembly (TW) of colorant, the content range of dyestuff can be from 0.5 % by weight to 80 % by weight, preferably from 1 % by weight to 50 % by weight.If the content of dyestuff in above-mentioned scope, can prevent the reliability variation of the wash-out such as dyestuff being caused by organic solvent after patterning, keep excellent photonasty simultaneously.
The content of red stain is not particularly limited, and still, for example, according to solids content, for the general assembly (TW) of described photosensitive composition, the content of red stain can be from 5 % by weight to 60 % by weight, preferably, and from 10 % by weight to 45 % by weight.If the content of red stain in above-mentioned scope, pixel there is sufficient color density and during developing the loss of non-pixel portion do not reduce.Therefore, can reduce the appearance of residue.
Red stain is added in composition to be blended in equably in composition with the form of dispersion.This dispersion can be produced, and except red stain, it comprises the spreading agent and the solvent that are generally used for composition.
Add spreading agent to allow the stability of decondensation and maintenance pigment and dyestuff, spreading agent can comprise conventional in the prior art spreading agent and not restriction.Preferably, can use acrylate spreading agent, for example, butyl methacrylate (BMA) or methacrylic acid N, N-dimethylaminoethyl (DMAEMA); Polycarboxylate; Unsaturated polyester acid amides; Poly carboxylic acid; (part) amine salt of poly carboxylic acid; The ammonium salt of poly carboxylic acid; The alkylamine salt of poly carboxylic acid; Polysiloxane; Long-chain polyaminoamide phosphate; The polycarboxylate that contains hydroxyl and its modified product; The acid amides or its salt that form by the polyester that contains free carboxy and the reaction that gathers (low-grade alkylidene imines); Water soluble resin or water-soluble polymeric compounds, for example, (methyl) acrylic acid-styrol copolymer, (methyl) acrylic acid-(methyl) acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol (PVA) or polyvinyl pyrrolidone etc.; Polyester; Modified polyacrylate; The addition product of ethylene oxide/propylene oxide; Phosphate etc.These compounds can use separately or with two or more be used in combination wherein.
For example, in the present invention, available commercial dispersants can comprise: DISPER BYK-160, DISPERBYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPERBYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184, DISPERBYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150(BYKChemicals); EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800(BASF company); SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10(Lubirzol company); HINOACTT-6000, HINOACT T-7000, HINOACT T-8000(Kawaken Fine Chemical company); AJISPUR PB-821, AJISPUR PB-822, AJUSPUR PB-823(Ajinomoto company); FLORENE DOPA-17HF, FLORENE DOPA-15BHF, FLORENE DOPA-33, FLORENE DOPA-44(Kyoeisha Chemicals) etc., these spreading agents can use separately or with two or more be used in combination wherein.
The content of spreading agent is not particularly limited, and still, for example, according to solids content, for the pigment of 100 weight portions, the content of spreading agent can be from 5 weight portion to 60 weight portions, preferably, and from 15 weight portion to 50 weight portions.If the content of spreading agent is in above-mentioned scope, pigment forms suitably subparticle and red stain can have required viscosity.
< alkali soluble resins >
In the time comprising the ethylenically unsaturated monomers with carboxyl, alkali soluble resins is aggregated.The ethylenically unsaturated monomers with carboxyl is the component of giving solubility property to alkaline developer used in developing process in the time forming pattern.
The ethylenically unsaturated monomers with carboxyl is not particularly limited, but can comprise, for example: monocarboxylic acid (such as acrylic acid, methacrylic acid, butenoic acid etc.); Dicarboxylic acid (such as fumaric acid, mesaconic acid (methaconicacid) and itaconic acid etc. with and acid anhydrides); There is list (methyl) acrylate of the polymkeric substance of carboxyl and hydroxyl at its two ends, such as ω-carboxyl polycaprolactone list (methyl) acrylate etc., preferably, acrylic acid and methacrylic acid, these materials can use separately or with two or more be used in combination wherein.
The acid number scope of alkali soluble resins can be from 30mg KOH/g to 170mg KOH/g, preferably, and from 50mg KOH/g to 160mg KOH/g.If the acid number of alkali soluble resins is in above-mentioned scope, resin and dyestuff are more compatible to prevent that dyestuff from separating out, and photosensitive composition can have excellent storage stability to keep required viscosity and developing powder fully.
In order to ensure the further developing performance of alkali soluble resins, this resin can have hydroxyl.
Provide the method for hydroxyl to be not particularly limited to alkali soluble resins, but can comprise, for example: in resin polymerization, further add the ethylenically unsaturated monomers with hydroxyl; Resin reacts with the compound with glycidyl; There is the ethylenically unsaturated monomers of hydroxyl and the multipolymer of polymerization reacts with the compound with glycidyl etc. by other interpolation.
The ethylenically unsaturated monomers with hydroxyl is not particularly limited, but can comprise, for example, (methyl) 2-Hydroxy ethyl acrylate, (methyl) 2-hydroxypropyl acrylate, (methyl) acrylic acid-4-hydroxyl butyl ester, 2-hydroxyl-3-phenoxy propyl (methyl) acrylate, N-hydroxyethyl acrylamide etc., preferably, (methyl) 2-Hydroxy ethyl acrylate.These materials can use separately or with two or more be used in combination wherein.
The compound with glycidyl is not particularly limited, but can comprise, for example, butyl glycidyl ether, propyl glycidyl ether, phenyl glycidyl ether, 2-ethylhexyl glycidol ether, glycidyl butyl ester, glycidyl methyl ether, ethyl ether, isopropyl glycidyl ether, tert-butyl group glycidol ether, benzyl glycidyl ether, 4-p t butylbenzoic acid ethylene oxidic ester, stearic acid ethylene oxidic ester, arylolycidyl ethers, glycidyl methacrylate etc., preferably butyl glycidyl ether, arylolycidyl ethers and glycidyl methacrylate.These materials can use separately or with two or more be used in combination wherein.
Can be aggregated according to alkali soluble resins of the present invention, also comprise simultaneously can copolymerization with aforementioned monomer at least one other monomer.For example, aromatic ethenyl compound, for example, styrene, vinyltoluene, methyl styrene, to chlorostyrene, O-methoxy styrene, meta-methoxy styrene, to methoxy styrene, adjacent vinyl benzyl methyl ether, a vinyl benzyl methyl ether, to vinyl benzyl methyl ether, adjacent vinyl benzyl glycidol ether, a vinyl benzyl glycidol ether, to vinyl benzyl glycidol ether etc.; The maleimide compound that N-replaces, such as aminomethyl phenyl maleimide, N-p-methylphenyl maleimide, N-o-methoxyphenyl maleimide, N-m-methoxyphenyl maleimide, N-p-methoxyphenyl maleimide etc. between hydroxy phenyl maleimide, N-p-hydroxybenzene maleimide, N-o-methyl-phenyl-maleimide, N-between N-N-cyclohexylmaleimide, N-benzyl maleimide, N-phenylmaleimide, N-o-hydroxy-phenyl maleimide, N-; (methyl) alkyl acrylate, for example (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) acrylic acid n-propyl, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate etc.; Alicyclic (methyl) acrylate, for example (methyl) acrylic acid ring pentyl ester, (methyl) cyclohexyl acrylate, 2-methylcyclohexyl (methyl) acrylate, three ring [5.2.1.0.2.6] decane-8-base (methyl) acrylate, 2-bis-cyclopentyl oxygen ethyl (methyl) acrylate, isobornyl (methyl) acrylate etc.; (methyl) acrylic acid aryl ester, for example (methyl) phenyl acrylate, (methyl) acrylic acid benzyl ester etc.; Unsaturated oxetane compound, for example, 3-(methacryloxy methyl) oxetanes, 3-(methacryloxy methyl)-3-Ethyloxetane, 3-(methacryloxy methyl)-2-trifluoromethyl oxetanes, 3-(methacryloxy methyl)-2-phenyl oxetanes, 2-(methacryloxy methyl) oxetanes, 2-(methacryloxy methyl)-4-trifluoromethyl oxetanes etc., these materials can use separately or with two or more be used in combination wherein.
The content of alkali soluble resins is not particularly limited, but for example according to solids content, and for the general assembly (TW) of described photosensitive composition, the content range of alkali soluble resins can be from 10 % by weight to 80 % by weight, preferably, and from 10 % by weight to 70 % by weight.If the content of alkali soluble resins is in above-mentioned scope, it can have enough solubility properties can easily form pattern in developer, and can prevent that the film in the pixel portion of exposed portion during developing from reducing, thereby cause reducing of non-pixel portion loss.
Below by the preparation method's of description alkali soluble resins embodiment.
By aforementioned monomer, add in the flask that is provided with stirrer, thermometer, backflow cooling tube, titration apparatus and nitrogen introduction pipe line with respect to the solvent of 0.5 times to 20 times of content of monomer and with respect to the polymerization initiator of the molar weight 0.1% to 10% of monomer, replace with nitrogen subsequently.Then, it is stirred 1 hour to 10 hours at 40 DEG C to 140 DEG C.
Above-mentioned solvent used herein can be any common solvent for free radical polymerization, for example, it comprises: be selected from tetrahydrofuran, dioxane, ethylene glycol dimethyl ethyl, diethylene glycol dimethyl ethyl, acetone, methyl ethyl ketone, methylisobutylketone, cyclohexanone, ethyl acetate, butyl acetate, propylene glycol monomethyl ethyl acetate, 3-methoxyl butylacetic acid ester, methyl alcohol, ethanol, propyl alcohol, normal butyl alcohol, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, toluene, dimethylbenzene, ethylbenzene, any in chloroform and dimethyl sulfoxide, these materials can use separately or use with their potpourri.
Polymerization initiator can be any initiating agent conventional in correlation technique and being not particularly limited.More specifically, can comprise: organic peroxide, such as di-isopropylbenzene hydroperoxide, di-tert-butyl peroxide, benzoyl peroxide, tert-butyl peroxide isobutyl carbonate propyl ester, peroxidating tertiary pentyl-2-ethyl hexanoate, tert-butyl peroxide-2-ethyl hexanoate etc.; And nitrogen compound, for example 2,2'-azoisobutyronitrile, 2,2'-azo two (2,4-methyl pentane nitrile), dimethyl-2,2'-azo two (2 Methylpropionic acid ester) etc., these materials can use separately or with two or more be used in combination wherein.
In order to be controlled at the molecular weight in aforementioned process, α-methylstyrenedimer or the compound containing sulfydryl can be used as chain-transferring agent.For the monomer of 100 weight portions, such α-methylstyrenedimer or the consumption containing the compound of sulfydryl can be 0.005 weight portion to 5 weight portions.About the condition of polymerization, according to the heat release value of polymerization or Preparation equipment consideration, feed process or temperature of reaction can suitably be controlled.
< photopolymerization compound >
Photopolymerization compound is the component that strengthens pattern intensity, can comprise simple function group monomer, bifunctional monomer or polyfunctional monomer etc., preferably bifunctional monomer or polyfunctional monomer.For example, these monomers' concrete example can comprise: simple function group monomer, as nonyl phenyl carbitol acrylate, 2-hydroxyl-3-phenoxy propyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxy ethyl methacrylate, NVP etc., bifunctional monomer, as two (acryloxy ethyl) ethers, 3-methyl pentanediol two (methyl) acrylate etc. of 1,6-hexanediol two (methyl) acrylate, two (methyl) acrylic acid glycol ester, neopentyl glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, bisphenol-A, polyfunctional monomer, as trimethylolpropane tris (methyl) acrylate, trimethylolpropane tris (methyl) acrylate of ethoxylation, propenoxylated trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, pentaerythrite six (methyl) acrylate of ethoxylation, propenoxylated dipentaerythritol six (methyl) acrylate, dipentaerythritol six (methyl) acrylate etc., these monomers use separately or with two or more be used in combination wherein.
The content of photopolymerization compound is not particularly limited, still, and for example, according to solids content, for the general assembly (TW) of described photosensitive composition, the content range of photopolymerization compound can be from 5 % by weight to 45 % by weight, preferably, and from 7 % by weight to 45 % by weight.If the content of photopolymerization compound is in above-mentioned scope, pixel portion can have favourable intensity or smoothness.
< antioxidant >
Antioxidant used can comprise the antioxidant functional group based on phenol and the antioxidant functional group based on phosphorus or the antioxidant functional group based on phenol and the antioxidant functional group based on sulphur in the present invention.By comprising such antioxidant, can prevent change color, excellent transmittance can be obtained and photosensitive reduction can be suppressed, be suppressed at thus the layering of pattern in developing process.
The antioxidant with the antioxidant functional group based on phenol and the antioxidant functional group based on phosphorus is not particularly limited, but can comprise, for example, 3,5-, bis--tertiary butyl-4-hydroxy benzyl phosphoric acid, 6-[3-(3-tertiary butyl-4-hydroxy-5-methyl) propoxyl group]-2,4,8,10-, tetra--tert-butyl group dibenzo [d, f] [1,3,2]-dioxy phosphorus heterocycle heptane etc.The concrete example of commercially available prod can comprise IRGANOX1425(BASF company manufacture), SumilizerGP(Sumitomo Chemicals company manufacture) etc.
Having antioxidant functional group based on phenol and the antioxidant functional group based on sulphur is not particularly limited, but can comprise, two [the 3-(3 of for example sulfo-diethylene, 5-bis--tert-butyl-hydroxy phenyl) propionic ester], 2,2 '-thiobis (6-tert-butyl-4-methyl-Phenol), 2, two (dodecyl the sulfidomethyl)-6-methylphenols of 4-etc.The concrete example of commercially available prod can comprise IRGANOX1035(BASF company manufacture), IRGANOX1081(BASF company manufacture), IRGANOX1726(BASF company manufacture) etc.
These antioxidants as described above can use separately or with two or more be used in combination wherein.
The content of antioxidant is not particularly limited, and still, for example, according to solids content, for the content of Photoepolymerizationinitiater initiater, the content range of antioxidant can be from 1 % by weight to 100 % by weight, preferably from 2 % by weight to 50 % by weight.Keep high photosensitivity if the content of antioxidant in above-mentioned scope, can reduce change color simultaneously, and then improve transmittance.
< Photoepolymerizationinitiater initiater >
Can comprise the compound representing by following formula 1 according to Photoepolymerizationinitiater initiater of the present invention:
[formula 1]
Wherein, R 1expression-R 4-R 5; R 2and R 3respectively to there is 1 alkyl to 8 carbon atoms, phenyl, benzyl or diphenyl sulfide based, described alkyl, phenyl, benzyl or diphenyl sulfide based be unsubstituted or by hydroxyl or there is 1 alkyl to 8 carbon atoms and replace; R 4to there is 1 alkylidene to 4 carbon atoms; And R 5to there are 3 naphthenic base to 8 carbon atoms.
The Photoepolymerizationinitiater initiater being represented by formula 1 can prevent because the light sensitivity that dyestuff causes reduces, and the effective photopolymerization performance of the photosensitive composition that comprises dyestuff is provided thus.Therefore, if Photoepolymerizationinitiater initiater uses with antioxidant combination according to the present invention, thereby the decline of light sensitivity can be maximized the further effect that is suppressed at pattern layering in developing process that improves.
Except the Photoepolymerizationinitiater initiater being represented by formula 1, photosensitive composition of the present invention also can be included at least one Photoepolymerizationinitiater initiater conventional in correlation technique.For example, can comprise: aceotphenone compound, benzophenone cpd, triaizine compounds, united imidazole, thioxanthones compound etc.These compounds can use separately or with two or more be used in combination wherein.
Aceotphenone compound is not particularly limited, but can comprise, for example diethoxy acetophenone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, benzyl dimethyl ketal, 2-hydroxyl-1-[4-(2-hydroxyl-oxethyl) phenyl]-2-methyl isophthalic acid-acetone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-(4-methyl thio phenyl)-2-morpholinyl-1-acetone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-1-butanone, 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl]-1-acetone, 2-(4-methyl-benzyl)-2-(dimethylamino)-1-(4-morpholinyl phenyl)-1-butanone etc.
Benzophenone cpd is not particularly limited; but can comprise; for example benzophenone, o-benzoyl methyl benzoic acid ester, 4-phenyl benzophenone, 4-benzoyl-4'-dimethyl diphenyl sulfide, 3; 3'; 4; 4'-tetra-(tert-butyl hydroperoxide carbonyl) benzophenone, 2,4,6-tri-methyl benzophenone etc.
Triaizine compounds is not particularly limited, but can comprise, for example 2, two (the trichloromethyl)-6-(4-methoxyphenyls of 4-)-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl naphthyls of 4-)-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-of 4-piperonyl-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl-styrenes of 4-)-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(5-methylfuran-2-yls of 4-) vinyl]-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(furans-2-yls of 4-) vinyl]-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(4-lignocaine-2-aminomethyl phenyls of 4-) vinyl]-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(3 of 4-, 4-Dimethoxyphenyl) vinyl]-1, 3, 5-triazine etc.
United imidazole is not particularly limited, but can comprise, for example 2, two (the 2-chlorphenyls)-4 of 2'-, 4', 5, 5'-tetraphenyl bisglyoxaline, 2, 2'-two (2, 3-dichlorophenyl)-4, 4 ', 5, 5'-tetraphenyl bisglyoxaline, 2, two (the 2-chlorphenyls)-4 of 2'-, 4', 5, 5'-tetra-(alkoxyl phenyl) bisglyoxaline, 2, two (the 2-chlorophenyls)-4 of 2'-, 4', 5, 5'-tetra-(tri-alkoxy phenyl) bisglyoxaline, 2, 2-two (2, 6-dichlorophenyl)-4, 4 ', 5, 5'-tetraphenyl-1, 2'-bisglyoxaline, or in aforesaid compound, have 4, 4', 5, any imidazolium compounds of the phenyl that 5' position is replaced by alkyl carbonic acyl radical, preferably, 2, two (the 2-chlorphenyls)-4 of 2'-, 4', 5, 5'-tetraphenyl bisglyoxaline, 2, 2'-two (2, 3-dichlorophenyl)-4, 4', 5, 5'-tetraphenyl bisglyoxaline, 2, 2-two (2, 6-dichlorophenyl)-4, 4', 5, 5'-tetraphenyl-1, 2'-bisglyoxaline etc.
Thioxanthones compound is not particularly limited, but can comprise, for example ITX, 2,4-diethyl thioxanthone, 2,4-bis-clopenthixal ketones, the chloro-4-propoxyl group of 1-thioxanthones etc.
The content of Photoepolymerizationinitiater initiater is not particularly limited, still, and for example, according to solids content, for the summation of the content of alkali soluble resins and photopolymerization compound, the content range of Photoepolymerizationinitiater initiater can be from 0.1 % by weight to 40 % by weight, preferably, and from 1 % by weight to 30 % by weight.If the content of Photoepolymerizationinitiater initiater is in above-mentioned scope, the light sensitivity of photosensitive composition uprises to reduce the time shutter, thereby has improved throughput rate and kept high resolution.In addition, the pixel portion forming can have favourable intensity, and can realize good smoothness on the surface of pixel portion.
In this Photoepolymerizationinitiater initiater as described above, the content of the compound being represented by formula 1 is not particularly limited, but, for example, for the general assembly (TW) of Photoepolymerizationinitiater initiater, the content range of the compound being represented by formula 1 can be from 10 % by weight to 100 % by weight, preferably, from 20 % by weight to 100 % by weight.If the content of the compound that through type 1 represents, in above-mentioned scope, can maximize the photosensitive effect of improving.
< photopolymerization causes reinforcing agent >
Photosensitive composition of the present invention also can comprise that photopolymerization causes reinforcing agent to improve photonasty.
Photopolymerization causes reinforcing agent and is not particularly limited, but can comprise, such as amines, carboxylic acid compound or there is the organosulfur compound etc. of sulfydryl, and these materials can use separately or with two or more be used in combination wherein.
Amines is not particularly limited, but can comprise, for example fatty amine, as triethanolamine, methyldiethanolamine, triisopropanolamine etc.; Aromatic amine, as 4-dimethylaminobenzoic acid methyl esters, 4-dimethyl ethyl aminobenzoate, 4-dimethylaminobenzoic acid isopentyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, 2-dimethylaminoethyl benzoic ether, N, N-dimethyl-p-toluidine, 4, two (dimethylamino) benzophenone, 4 of 4'-, two (lignocaine) benzophenone of 4'-etc.
Carboxylic acid compound is not particularly limited, but can comprise, the assorted acetic acid of for example aromatic series, as phenyl thioacetic acid, aminomethyl phenyl thioacetic acid, ethylphenyl thioacetic acid, Methylethyl phenyl thioacetic acid, 3,5-dimethylphenyl thioacetic acid, methoxyphenyl thioacetic acid, Dimethoxyphenyl thioacetic acid, chlorphenyl thioacetic acid, dichlorophenyl thioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthyl thioacetic acid, N-naphthyl aminoacetic acid, naphthoxy acetic acid etc.
The organosulfur compound with sulfydryl is not particularly limited, but can comprise, for example, 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, trimethylolpropane tris (3-mercaptopropionic acid ester), pentaerythrite four (3-sulfydryl butyric ester), pentaerythrite four (3-mercaptopropionic acid ester), dipentaerythritol six (3-mercaptopropionic acid ester), TEG two (3-mercaptopropionic acid ester) etc.
The content that photopolymerization causes reinforcing agent is not particularly limited, but, for example, according to solids content, for the general assembly (TW) of photosensitive composition, the content range of photopolymerization initiation reinforcing agent can be from 0.1 % by weight to 40 % by weight, preferably from 1 % by weight to 30 % by weight.If photopolymerization causes the content of reinforcing agent in above-mentioned scope, the photonasty of photosensitive composition can further be enhanced, thereby boosts productivity.
< solvent >
As long as the present invention's solvent used can dissolve aforementioned component, the present invention's solvent used has no particular limits, but can comprise, such as ether, aromatic hydrocarbon, ketone, alcohol, ester etc., these materials can use separately or with two or more be used in combination wherein.
The concrete example of solvent can comprise: ethylene glycol monoalkyl ether, for example, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol ether, ethylene glycol monobutyl ether etc.; Ether, such as diethylene glycol dimethyl ether, diethyl carbitol, diglycol dipropyl ether, diethylene glycol dibutyl ether, methyl glycol acetate, ethyl cellosolve acetate, dihydroxypropane single-ether acetate, propylene glycol monopropyl ether acetate, methoxyl butylacetic acid ester, methoxyl amyl group acetate etc.; Aromatic hydrocarbon, for example, benzene,toluene,xylene, sym-trimethyl benzene etc.; Ketone, for example, methyl ethyl ketone, acetone, methylpentanone, methyl isobutyl ketone, cyclohexanone etc.; Alcohol, for example, ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, glycol, glycerine etc.; Ester, for example, 3-ethoxyl ethyl propionate, 3-methoxy methyl propionate, gamma-butyrolacton etc., preferably, can use propylene glycol monomethyl ether acetate, dihydroxypropane single-ether acetate, cyclohexanone, ethyl lactate, butyl lactate, 3-ethoxyl ethyl propionate, 3-methoxy methyl propionate.
On aspect applicability and drying property, solvent preferably has the organic solvent of the boiling point of 100 DEG C to 200 DEG C.
The content of solvent is not particularly limited, but for example, this solvent can be included in the solvent comprising in colorant dispersion, for the general assembly (TW) of photosensitive composition, the total content scope of this solvent can be from 60 % by weight to 90 % by weight, preferably from 70 % by weight to 85 % by weight.If the content of solvent, in above-mentioned scope, can obtain favourable applicability.
< adjuvant >
Photosensitive composition of the present invention also can comprise any adjuvant that is selected from alternative polymerizable compound, hardening agent, surfactant, adhesion enhancer, UV absorbing agent and anti-coagulants etc.
This alternative polymerizable compound is not particularly limited, but can comprise, for example curable resin, such as epoxy resin, maleimide resin etc., thermoplastic resin, such as polyvinyl alcohol (PVA), polyacrylic acid, polyalkylene glycol monoalkyl ether, poly-fluoroalkyl acrylate, polyester, polyurethane etc.
This hardening agent is the component of solidifying and increase physical strength for degree of depth segmentation, and the kind of this hardening agent is not particularly limited, but can comprise, such as epoxy compound, many functional group isocyanates's compound, melamine compound, oxetane compound etc.
Epoxy compound is not particularly limited, but can comprise, for example, the brominated derivative of bisphenol A epoxide resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, A Hydrogenated Bisphenol A F epoxy resin, novalac epoxy, other aromatic epoxy resins, cycloaliphatic epoxy resin, glycidyl ester type resin, glycidic amine type resin or epoxy resin; Aliphatic, alicyclic or aromatic epoxy compound except epoxy resin and its brominated derivative, butadiene (being total to) polymer ring oxide; Isoprene (being total to) polymer ring oxide; Glycidyl (methyl) acrylate (being total to) polymkeric substance; Three-glycidyl based isocyanate etc.
Oxetane compound is not particularly limited, but can comprise, for example, and dioxetane carbonic ester, dimethylbenzene dioxetane, dioxetane adipate, dioxetane terephthalate, cyclohexane dicarboxylic acid dioxetane etc.
Hardening agent can with can the epoxy radicals of ring-opening polymerization epoxy compound or the auxiliary curing agent compound of the oxetanes main chain of oxetane compound compatible.
Auxiliary curing agent compound is not particularly limited, but can comprise, for example polyvalent carboxylic acid, polyvalent carboxylic acid's acid anhydride, acid producing agent etc.Polyvalent carboxylic acid's acid anhydride can comprise any epoxy curing agent that can buy on market.
In the present invention, operable these commercially available epoxy curing agents are not particularly limited, but can comprise, for example, Adekahadona EH-700(trade name, manufactured by Adeka Engineering company limited), Likashitdo HH(trade name, manufactured by New Japan Chemicals company limited), MH-700(trade name, manufactured by New Japan Chemicals company limited) etc.
Surfactant is the component of improving the coated molded property of photosensitive resin composition, and its kind is not particularly limited, but can comprise, for example, and fluorine surfactant, silicon surface active agent or its potpourri.
Silicon surface active agent is not particularly limited, but can comprise commercially available prod, for example: DC3PA, DC7PA, SH11PA, the SH21PA, the SH8400 etc. that are manufactured by Dow-corningDoray Silicon company; TSF-4440, the TSF-4300, TSF-4445, TSF-4446, TSF-4460, the TSF-4452 etc. that are manufactured by GE Toshiba Silicon company.
Fluorine surfactant is not particularly limited, but can comprise commercially available prod, for example: the Mega pieces F-470, F-471, F-475, F-482, the F-489 etc. that are manufactured by Dainippon InkChemical Industries.
The kind of adhesion enhancer is not particularly limited, but can comprise, for example vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-aminoethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-aminoethyl)-3-aminopropyl trimethoxysilane, 3-aminopropyl triethoxysilane, 3-glycidyl ether oxygen base propyl trimethoxy silicane, 3-glycidyl ether oxygen base propyl group dimethoxy silane, 2-(3, 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-methacryloxypropyl trimethoxy silane, 3-sulfydryl propyl trimethoxy silicane, 3-isocyanates propyl trimethoxy silicane, 3-isocyanates propyl-triethoxysilicane etc., these materials can use separately or with two or more be used in combination wherein.
The content of adhesion enhancer is not particularly limited, and still, for example, according to solids content, for the general assembly (TW) of photosensitive composition, the content range of adhesion enhancer can be from 0.01 % by weight to 10 % by weight, preferably, and from 0.05 % by weight to 2 % by weight.
The kind of UV absorbing agent is not particularly limited, but can comprise, for example, the 2-(3-tert-butyl group-2-hydroxy-5-methyl base phenyl)-5-chlorobenzotriazole, alkoxy benzophenone etc.
Anti-coagulants is not particularly limited, but can comprise, for example sodium polyacrylate.
the preparation > of < photosensitive composition
Can comprise according to the preparation method of photosensitive composition of the present invention, for example: colorant and spreading agent are added in solvent and disperseed to prepare the colorant dispersion with single-size size; In solvent, dissolve alkali soluble resins, photopolymerization compound, Photoepolymerizationinitiater initiater and other adjuvants if needed, these materials are mixed with above-mentioned colorant dispersion; And, alternatively, also add new solvent.
< color filter >
In addition, the invention provides the color filter that uses above-mentioned photosensitive composition to manufacture.
The color layer that color filter comprises substrate and forms at substrate top.
Substrate can be that therefore, substrate is not particularly limited for a part that is provided with color filter for original substrate or the display of color filter itself.Substrate can be glass, silicon (Si), monox (SiO x) or polymeric substrates, polymeric substrates can be made up of polyethersulfone (PES), polycarbonate (PC) etc.
Dyed layer is the layer that contains photosensitive composition of the present invention, can be by upper applying photosensitive composition, exposure, development, then this coating heat curing is made to form required pattern to this layer.
The color filter with above-mentioned this substrate and dyed layer can also comprise the dividing plate being formed between each colored pattern and/or black matrix".In addition, color filter can comprise the protective seam being formed on dyed layer top.
< liquid crystal display >
In addition, the invention provides a kind of liquid crystal display of this color filter as described above that has.
Except thering is above-mentioned this color filter, can comprise technical configuration known in the correlation technique the present invention relates to according to liquid crystal display of the present invention, and it is not particularly limited.
Hereinafter, in order to understand more up hill and dale the present invention, will describe preferred embodiment.But, it is evident that for those skilled in the art, such embodiment is provided for exemplary purposes and appending claims is not particularly limited, various modifications and changes are feasible without departing from the scope and spirit of the present invention, and such modifications and changes are included in the present invention who limits as appended claim fully.
Embodiment
The preparation of Bei Li – colorant dispersion processed
Being prepared as follows of red colored agent dispersion: mix and disperse the AJISPER PB821(as spreading agent of C.I. paratonere 254,6 weight portions of 14 weight portions to manufacture by AJINOMOTO FineTechno company limited by bead mill) and comprise the solvent of the propylene glycol monomethyl ether acetate of 60 weight portions and the cyclohexanone of 20 weight portions, lasting 12 hours.
Synthesizing of He Cheng Li – alkali soluble resins
(1) synthesis example 1
120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ethers, 2 parts of azoisobutyronitriles (AIBN), 13.0 parts of acrylic acid, 10 parts of benzyl methacrylates, 57.0 parts of 4-methyl styrenes, 20 parts of methyl methacrylates and 3 parts of n-dodecyl mercaptans are incorporated in the flask that is provided with stirrer, thermometer, backflow cooling tube, titration apparatus and nitrogen introduction pipe line, and change the air in flask into nitrogen.Then temperature is elevated to 110 DEG C and stir in react 6 hours.The alkali soluble resins of synthesized has 100.2mg KOH/g(solid content) acid number and by approximately 15,110 measured weight-average molecular weight Mw of gel permeation chromatography (GPC).
(2) synthesis example 2
120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ethers, 2 parts of AIBN, 3.5 parts of acrylic acid, 10 parts of benzyl methacrylates, 66.5 parts of 4-methyl styrenes, 20 parts of methyl methacrylates and 3 parts of n-dodecyl mercaptans are incorporated in the flask that is provided with stirrer, thermometer, backflow cooling tube, titration apparatus and nitrogen introduction pipe line, and change the air in flask into nitrogen.Then, temperature is elevated to 110 DEG C and stir in react 6 hours.The alkali soluble resins of synthesized has 26.5mg KOH/g(solid content) acid number and by approximately 16,070 measured weight-average molecular weight Mw of GPC.
(3) synthesis example 3
120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ethers, 2 parts of AIBN, 22.5 parts of acrylic acid, 10 parts of benzyl methacrylates, 47.5 parts of 4-methyl styrenes, 20 parts of methyl methacrylates and 3 parts of n-dodecyl mercaptans are incorporated in the flask that is provided with stirrer, thermometer, backflow cooling tube, titration apparatus and nitrogen introduction pipe line, and change the air in flask into nitrogen.Then, temperature is elevated to 110 DEG C and stir in react 6 hours.The alkali soluble resins of synthesized has 172.3mg KOH/g(solid content) acid number and by approximately 14,850 measured weight-average molecular weight Mw of GPC.
Embodiment 1
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of acid red 52(is manufactured by TCI u s company), 14.7 parts of synthetic resin in synthesis example 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), the Irganox1035(as antioxidant of 0.2 part is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
[formula 2]
Embodiment 2
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of acid red 52(is manufactured by TCI u s company), 14.7 parts of synthetic resin in synthesis example 1, 4.9 parts of KAYARADDPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), the Sumilizer GP(as antioxidant of 0.2 part manufactures by Sumitomo Chemical company), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
Comparative example 1
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 25.5 parts of propylene glycol monomethyl ether acetate and 36.2 parts of propylene glycol monomethyl ethers.
Comparative example 2
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of antioxidant IRGANOX3114(based on phenol is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
Comparative example 3
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of antioxidant IRGAFOS168(based on phosphorus is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
Comparative example 4
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of IRGANOX3114(is manufactured by BASF AG), 0.2 part of IRGAFOS168(is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 35.8 parts of propylene glycol monomethyl ethers.
Comparative example 5
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of antioxidant STAB AO-412S(based on sulphur is manufactured by ADEKA company), 25.5 parts of propylene glycol monomethyl ether acetate and 35.8 parts of propylene glycol monomethyl ethers.
Comparative example 6
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of IRGANOX3114(is manufactured by BASF AG), 0.2 part of STAB AO-412S(is manufactured by ADEKA company), 25.5 parts of propylene glycol monomethyl ether acetate and 35.8 parts of propylene glycol monomethyl ethers.
Comparative example 7
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the Irgacure OXE02(with the structure that following formula 3 represents of 0.7 part is manufactured by BASF AG), 0.2 part of antioxidant Irganox1035(is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 35.8 parts of propylene glycol monomethyl ethers.
[formula 3]
Comparative example 8
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 1, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the Irgacure OXE02(with the structure that formula 3 represents of 0.7 part is manufactured by BASF AG), 0.2 part of antioxidant Sumilizer GP(is manufactured by Sumitomo Chemicals company), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
Comparative example 9
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 2, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of antioxidant Irganox1035(is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
Comparative example 10
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, 0.6 part of C.I. acid red 52(is manufactured by TCI u s company), synthetic resin in 14.7 parts of synthesis examples 3, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of antioxidant Irganox1035(is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
Comparative example 11
Being prepared as follows of photosensitive composition: mix 17.1 parts of colorant dispersion, synthetic resin in 14.7 parts of synthesis examples 3, 4.9 parts of KAYARAD DPHA(are manufactured by Nippon Chemical company), 0.3 part of Irgacure907(is manufactured by BASF AG), the TR-PBG-305(with the structure that formula 2 represents of 0.7 part is manufactured by TRONLY company), 0.2 part of antioxidant Irganox1035(is manufactured by BASF AG), 25.5 parts of propylene glycol monomethyl ether acetate and 36.0 parts of propylene glycol monomethyl ethers.
Experimental example 1
Pass through spin-coating method, the glass substrate that respectively every kind of photosensitive composition preparing is coated in to 2 inches at a certain angle in embodiment and comparative example (is manufactured by Corning Co., EAGLE XG) upper after, coated substrate is placed on heating plate and is retained at the temperature of 100 DEG C and keep 3 minutes, to form film.Then, the test light mask that has the pattern of the transmittance of stepped change in 1% to 100% scope and be of a size of lines/space pattern of 1 μ m to 50 μ m is placed on this film, is carrying out UV radiation apart from these test light mask 100 μ m places subsequently.At this, high-pressure mercury (Hg) lamp that is 1KW for the light source of UV radiation, this high-pressure sodium lamp contains all g rays, h ray and i ray, and with 100mJ/cm 2radiation intensity luminous.Be in 10.5 KOH developer solution by be immersed in pH value by the film of UV radiation, continue 2 minutes, thereby be developed.Utilizing after distilled water flushing scribbles the glass substrate of film, make it dry by be blown into nitrogen to this glass substrate, then in the oven heat of 200 DEG C, heat 25 minutes.Thereby form color filter.Above-mentioned formed color filter has the film thickness of 2.0 μ m.
(1) assessment of viscosity
The pattern forming by observation by light microscope, picks up according to the following criterion evaluation pattern that picks up (picking) for pattern.Evaluation result is as shown in table 1.
Zero: do not observe pattern and pick up
△: 1 to 3 pattern picks up
X:4 or more patterns pick up
(2) measurement of developing powder
Measured during developing until non-expose portion is dissolved the required time completely, measurement result is as shown in table 1.
Experimental example 2
Except not having to use for the photomask of testing, according to forming color filter with the same steps described in experimental example 1.
(1) variation and the aberration of measurement contrast
The substrate of the color filter forming is arranged between two polarization plates, be rotated and use fluorescent light (at the wavelength place of 380nm to 780nm) to illuminate from rear side simultaneously in one of them polarization plates of front side, to use CS-2000 nitometer (being manufactured by KONICA MINOLTA company) to measure radiative maximum intensity and minimum strength.Then the value of, calculating divided by minimum strength by maximum intensity defines contrast.
Aberration is colourity by before measuring respectively at 200 DEG C in heating furnace continuous heating 25 minutes and afterwards, then the colourity (y) after heating is deducted to the value that the colourity (y) before heating is calculated, its mathematical expression 1 use ' △ y ' expression below.
[mathematical expression 1]
△before after y=y(heating) – y(heats)
Measurement result is shown in table 1.
(2) measurement of transmittance
Use colour difference meter (manufacturing OSP-200 by Olympus company), measured the transmittance in visible region.Measurement result is as shown in table 1.
[table 1]
Ginseng sees the above table 1, can see, in embodiment 1 and embodiment 2, prepared composition has excellent viscosity and the layering of pattern, high developing powder, less aberration, the transmittance of excellence and high contrast do not occur.
Find through contrast, have excellent comprise viscosity, developing powder, aberration, contrast and transmittance characteristic color filter can not use according to composition prepared in comparative example 1 to 11 (at least one aforementioned properties is poor) and manufacture.

Claims (9)

1. a photosensitive composition, comprising: red stain, alkali soluble resins, photopolymerization compound, antioxidant, Photoepolymerizationinitiater initiater and solvent, wherein,
Described alkali soluble resins has the acid number of 30mg KOH/g to 170mg KOH/g;
Described antioxidant comprises the antioxidant functional group based on phenol and the antioxidant functional group based on phosphorus or the antioxidant functional group based on phenol and the antioxidant functional group based on sulphur;
Described Photoepolymerizationinitiater initiater comprises the compound being represented by following formula 1:
[formula 1]
Wherein R 1expression-R 4-R 5; R 2and R 3respectively to there is 1 alkyl to 8 carbon atoms, phenyl, benzyl or diphenyl sulfide based, described alkyl, phenyl, benzyl or diphenyl sulfide based be unsubstituted or by hydroxyl or there is 1 alkyl to 8 carbon atoms and replace; R 4to there is 1 alkylidene to 4 carbon atoms; And R 5to there are 3 naphthenic base to 8 carbon atoms.
2. composition according to claim 1, wherein, described alkali soluble resins has the acid number of 50mg KOH/g to 160mg KOH/g.
3. composition according to claim 1, wherein, described antioxidant is selected from 3,5-bis--tertiary butyl-4-hydroxy benzyl phosphoric acid, 6-[3-(3-tertiary butyl-4-hydroxy-5-methyl) propoxyl group]-2,4,8,10-tetra--tert-butyl group dibenzo [d, f] [1,3,2]-dioxy phosphorus heterocycle heptane, sulfo-diethylene two [3-(3,5-bis--tert-butyl-hydroxy phenyls) propionic ester], 2, at least one in 2 '-thiobis (6-tert-butyl-4-methyl-Phenol) and 2,4-bis-(dodecyl sulfidomethyl)-6-methylphenol.
4. composition according to claim 1, wherein, according to solids content, for the general assembly (TW) of described photosensitive composition, the percentage by weight of the amount of the described red stain comprising is 5% to 60%,
The percentage by weight of the amount of the described alkali soluble resins comprising is 10% to 80%, and
The percentage by weight of the amount of the described photopolymerization compound comprising is 5% to 45%,
According to solids content, by weight percentage, the amount of the described Photoepolymerizationinitiater initiater comprising account for described alkali soluble resins and described photopolymerization compound content sum 0.1% to 40%,
By weight percentage, the amount of the described antioxidant comprising account for described Photoepolymerizationinitiater initiater content 1% to 100%, and
The amount of the described solvent comprising by weight percentage, account for described photosensitive composition general assembly (TW) 60% to 90%.
5. composition according to claim 1, wherein, by weight percentage, the amount of the described compound being represented by formula 1 comprising account for described Photoepolymerizationinitiater initiater general assembly (TW) 10% to 100%.
6. composition according to claim 1, also comprises at least one Photoepolymerizationinitiater initiater being selected from aceotphenone compound, benzophenone cpd, triaizine compounds, united imidazole and thioxanthones compound.
7. composition according to claim 1, also comprises that at least one photopolymerization in the organosulfur compound that is selected from amines, carboxylic acid compound and contain sulfydryl causes reinforcing agent.
8. a color filter, described color filter uses and makes according to the photosensitive composition described in any one in claim 1 to 7.
9. a liquid crystal display, described liquid crystal display comprises color filter according to claim 8.
CN201410042815.6A 2013-02-06 2014-01-28 Photosensitive composition Active CN103969949B (en)

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