CN102736411B - Photosensitive resin composition, and color filter and liquid crystal display device using same - Google Patents

Photosensitive resin composition, and color filter and liquid crystal display device using same Download PDF

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CN102736411B
CN102736411B CN201210077899.8A CN201210077899A CN102736411B CN 102736411 B CN102736411 B CN 102736411B CN 201210077899 A CN201210077899 A CN 201210077899A CN 102736411 B CN102736411 B CN 102736411B
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acrylate
methyl
nitrogen
unsaturated monomer
acid
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CN102736411A (en
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许荣宾
林伯宣
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Chi Mei Corp
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Chi Mei Corp
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Abstract

A photosensitive resin composition and a color filter and a liquid crystal display device using the same are provided, wherein the alkali-soluble resin of the photosensitive resin composition comprises a first alkali-soluble resin, the first alkali-soluble resin is a polymerization reaction product of a mixture of a first unsaturated monomer containing a carboxylic group, a second unsaturated monomer containing an aromatic ring structure and a third unsaturated monomer containing an alicyclic structure, and the weight ratio of the second unsaturated monomer to the third unsaturated monomer is between 0.01 and 0.40. Therefore, the photosensitive resin composition has better developing performance in the photoetching process, the pixel coloring layer of the color filter has excellent sputtering resistance, and the liquid crystal display device has no bubble display defects.

Description

Photosensitive resin composition and use its colored filter and liquid crystal indicator
Technical field
The present invention relates to a kind of photosensitive resin composition and use its colored filter and liquid crystal indicator, refer to especially a kind of in lithographic process photosensitive resin composition, a kind of its pixel dyed layer of the splendid developability of tool formed and the colored filter of the splendid resistance to sputter of tool by this photosensitive resin composition, and a kind of this colored filter and liquid crystal indicator without blister display defect of using.
Background technology
The applications such as colour liquid crystal display device, colour facsimile apparatus, colour camera have been widely used in along with colored filter, the manufacturing technology of colored filter is quite variation also, as decoration method, print process, electrochemical plating, Pigments method etc., wherein with Pigments method for main flow instantly.
What is called is made colored filter with Pigments method, normally first on glass substrate, form with the metals such as crome metal/chromium oxide or photoresist the black matrix" (black matrix) that shading is used, again the photoresist (or claiming colorama resist) that is dispersed with red pigment is coated on this glass substrate, carry out subsequently mask exposure, develop to solidify and wait processing, to form red sub-pixel, repeat same step to form green sub-pixels successively on this glass substrate, blue subpixels, described red sub-pixel, green sub-pixels and blue subpixels are separated by this black matrix", so far just on this glass substrate, form pixel dyed layer, can first on this pixel dyed layer, form diaphragm depending on demand, then on this diaphragm, form nesa coating, finally cut, just can complete the making of this colored filter.
In the processing procedure of above-mentioned Pigments method, this photoresist is generally made up of pigment, alkali soluble resin, multi-functional monomer, light trigger and solvent, as Jap.P. Unexamined Patent 6-95211 case, Jap.P. Unexamined Patent 8-183819 case, disclose with Jap.P. Unexamined Patent 9-311210 case, this alkali soluble resin of using is common is for multipolymer that monomer component was aggregated into (methyl) acrylic acid.
But, simplify and high transmission rate for the processing procedure of pursuing colored filter, described diaphragm is omitted to the means that generally used for industry.But incident problem is, due to the omission of described diaphragm, in the sputter forming process of follow-up nesa coating, this pixel dyed layer will certainly be because cannot directly bearing the electronic strong bundle of sputter process, and produce cracking phenomenon.
In order to improve the problems referred to above, as shown in Jap.P. JP 2002-287352 case, alkali soluble resin composition in the photosensitive resin composition using, to be formed by the polymerization of unsaturated monomers containing aromatic derivant, thereby can increase the performance such as resistance to dry ecthing, resistance to sputter while forming the pixel dyed layer of colored filter with this photosensitive resin composition, even if but so, utilize the made colored filter of this photosensitive resin composition, when manufacturing liquid crystal indicator, but can produce the problem of blister display defect.
Summary of the invention
The object of the present invention is to provide a kind of in lithographic process the splendid developability of tool photosensitive resin composition, a kind of have by this photosensitive resin composition formed and the colored filter of the pixel dyed layer of the splendid resistance to sputter of tool, and a kind of this colored filter and liquid crystal indicator without blister display defect of using.
Photosensitive resin composition of the present invention, comprise alkali soluble resin, containing compound, light trigger, the organic solvent of ethene unsaturated group, and pigment, this alkali soluble resin comprises the first alkali soluble resin, this first alkali soluble resin is to have containing the first unsaturated monomer of carboxylic acid group, containing the second unsaturated monomer of aromatic ring structure, and containing the polymeric reaction product of the potpourri of the 3rd unsaturated monomer of alicyclic structure, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.40.
Photosensitive resin composition of the present invention, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.35.
Photosensitive resin composition of the present invention, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.30.
Photosensitive resin composition of the present invention, taking this mixture total weight as 100 weight portions, the content summation of this second unsaturated monomer and the 3rd unsaturated monomer is between 25 weight portion～60 weight portions.
Photosensitive resin composition of the present invention, this first unsaturated monomer is selected from acrylic acid, methacrylic acid, 2-methacryl ethoxy succinate, butenoic acid, α-chloroacrylic acid, ethylacrylic acid, cinnamic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, or these a combination.
Photosensitive resin composition of the present invention, this second unsaturated monomer is to be selected from styrene, α-methyl styrene, vinyltoluene, to chlorostyrene, divinylbenzene, benzyl methacrylate, benzyl acrylate, phenyl methyl acrylate, phenyl acrylate, 2-nitrobenzophenone acrylate, 4-nitrobenzophenone acrylate, 2-nitrobenzene methyl acrylate, 2-nitrobenzoyl ylmethyl acrylate, 2-nitrobenzophenone methacrylate, 2-Chlorophenylmethyl acrylate, 4-Chlorophenylmethyl acrylate, 2-chlorphenyl acrylate, 4-chlorphenyl acrylate, phenoxy group ethyl-methyl acrylate, phenoxy group polyethylene glycol acrylate, phenoxy group polyethylene glycol methacrylate-styrene polymer, Nonylphenoxy polyethylene glycol acrylate, Nonylphenoxy polyethylene glycol methacrylate-styrene polymer, nitrogen-phenyl maleimide, nitrogen-o-hydroxy phenyl maleimide, nitrogen-m-hydroxy phenyl maleimide, nitrogen-p-hydroxy phenyl maleimide, nitrogen-o-aminomethyl phenyl maleimide, nitrogen-m-aminomethyl phenyl maleimide, nitrogen-p-aminomethyl phenyl maleimide, nitrogen-o-methoxyphenyl maleimide, nitrogen-m-methoxyphenyl maleimide, nitrogen-p-methoxyphenyl maleimide, o-vinylphenol, m-vinylphenol, p-vinylphenol, 2-methyl-4-Vinyl phenol, 3-methyl-4-Vinyl phenol, o-isopropenyl phenol, m-isopropenyl phenol, p-isopropenyl phenol, 2-vinyl-1-naphthols, 3-vinyl-1-naphthols, 1-vinyl-beta naphthal, 3-vinyl-beta naphthal, 2-isopropenyl-1-naphthols, 3-isopropenyl-1-naphthols, o-methoxy styrene, m-methoxy styrene, p-methoxystyrene, o-methoxy styrene, m-methoxy styrene, p-methoxy styrene, o-(vinyl benzene methyl) glycidyl ethers, m-(vinyl benzene methyl) glycidyl ethers, p-(vinyl benzene methyl) glycidyl ethers, indenes, acetyl group naphthalene, or these a combination.
Photosensitive resin composition of the present invention, the 3rd unsaturated monomer be selected from have dicyclo amyl group unsaturated compound, there is the unsaturated compound of double cyclopentenyl or these a combination.
Photosensitive resin composition of the present invention, the 3rd unsaturated monomer is selected from (methyl) acrylic acid dicyclo pentyl ester, (methyl) acrylic acid dicyclo amyl group oxidation ethyl ester, (methyl) acrylic acid dicyclopentenyloxyethyl methacrylate, (methyl) acrylic acid dicyclo amylene oxidation ethyl ester, or these a combination.
Photosensitive resin composition of the present invention, this potpourri also has the 4th unsaturated monomer.
Photosensitive resin composition of the present invention, the 4th unsaturated monomer is selected from nitrogen-N-cyclohexylmaleimide, methyl acrylate, ethyl acrylate, acrylic acid n-propyl, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, tert-butyl acrylate, acrylic acid 2-hydroxy methacrylate, acrylic acid 2-hydroxy propyl ester, acrylic acid 3-hydroxy propyl ester, acrylic acid 2-hydroxyl butyl ester, acrylic acid 3-hydroxyl butyl ester, acrylic acid 4-hydroxyl butyl ester, allyl acrylate, acrylic acid triethylene glycol methoxyethoxy ester, nitrogen, nitrogen-dimethylamino ethyl acrylate, nitrogen, nitrogen-diethylamino propyl acrylate, nitrogen, nitrogen-dibutylamino propyl acrylate, acrylic acid epoxy propyl diester, methyl methacrylate, β-dimethyl-aminoethylmethacrylate, n propyl methacrylate, isopropyl methacrylate, n-BMA, isobutyl methacrylate, the secondary butyl ester of methacrylic acid, Tert-butyl Methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxy propyl ester, methacrylic acid 3-hydroxy propyl ester, methacrylic acid 2-hydroxyl butyl ester, methacrylic acid 3-hydroxyl butyl ester, methacrylic acid 4-hydroxyl butyl ester, allyl methacrylate, methacrylic acid triethylene glycol methoxyethoxy ester, lauryl methacrylate, methacrylic acid myristyl ester, methacrylic acid cetyl ester, methacrylic acid stearyl, methacrylic acid eicosyl ester, methacrylic acid docosyl ester, methacrylic acid nitrogen, nitrogen-dimethylamino ethyl ester, nitrogen, nitrogen-dimethylaminomethyl propyl acrylate, nitrogen-iso-butyl amino methyl ethyl acrylate, methacrylic acid glycidyl ester, vinyl acetate, propionate, vinyl butyrate, methoxy ethylene, ethyl vinyl ether, allyl glycidyl ethers, methylallyl glycidyl ethers, vinyl cyanide, methacrylonitrile, α-chloro-acrylonitrile, the sub-ethene of cyaniding, acrylamide, Methacrylamide, α-chloropropene acid amides, nitrogen-hydroxyethyl acrylamide, nitrogen-hydroxyethyl methacrylamide, 1,3-butadiene, isopentene, chlorination butadiene, or these a combination.
Photosensitive resin composition of the present invention, taking this mixture total weight as 100 weight portions, the content of this first unsaturated monomer is between 20 weight portion～60 weight portions, the content of this second unsaturated monomer is between 0.5 weight portion～20 weight portion, the content of the 3rd unsaturated monomer is between 20 weight portion～50 weight portions, and the content of the 4th unsaturated monomer is between 0 weight portion～15 weight portion.
Photosensitive resin composition of the present invention, this alkali soluble resin also comprises the second alkali soluble resin, this second alkali soluble resin comprises the monomer of (1) structure that has formula:
formula (1)
In formula, R 1and R 2represent respectively hydrogen atom, C 1～C 5alkyl, the phenyl of straight or branched, or halogen atom.
Photosensitive resin composition of the present invention, taking this alkali soluble resin gross weight as 100 weight portions, the content of this first alkali soluble resin is between 30 weight portion～90 weight portions.
Photosensitive resin composition of the present invention, taking this alkali soluble resin gross weight as 100 weight portions, the content of this second alkali soluble resin is between 10 weight portion～70 weight portions.
Photosensitive resin composition of the present invention, taking this alkali soluble resin gross weight as 100 weight portions, should be containing the content of the compound of ethene unsaturated group between 10 weight portion～500 weight portions, the content of this light trigger is between 2 weight portion～200 weight portions, the content of this organic solvent is between 500 weight portion～5000 weight portions, and the content of this pigment is between 100 weight portion～800 weight portions.
Photosensitive resin composition of the present invention, should be selected from the first compound, the second compound containing the compound of ethene unsaturated group, or these a combination, this first compound is to be reacted and obtain with (methyl) acrylic acid by the polyvalent alcohol of caprolactone upgrading.
Photosensitive resin composition of the present invention, this first compound has suc as formula structure shown in (2):
formula (2)
In formula, R 9and R 10represent respectively hydrogen or methyl, the integer that m is 1～2, a+b=2～6, the integer that a is 1～6, the integer that b is 0～5.
Photosensitive resin composition of the present invention, this second compound has suc as formula functional group shown in (3):
formula (3)
In formula, R 11represent respectively hydrogen or methyl.
Colored filter of the present invention, comprises the pixel dyed layer being formed after photoetching treatment by this photosensitive resin composition.
Liquid crystal indicator of the present invention, comprises this colored filter.
Effect of the present invention is, this photosensitive resin composition is this potpourri that this first unsaturated monomer, this second unsaturated monomer and the 3rd unsaturated monomer are mixed to get, and then this first alkali soluble resin of copolymerization, based on these potpourri 100 weight portions, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.40.Therefore, allow this photosensitive resin composition in lithographic process, have preferably developability, allow and use this photosensitive resin composition to form the colored filter of this pixel dyed layer, its pixel dyed layer can have splendid resistance to sputter, further, allow and use the made liquid crystal indicator of this colored filter, completely without blister display defect.
Embodiment
Head is noted that, in this article, should (methyl) acrylate " (meth) acrylate " represent acrylate (acrylate) and/or methacrylate (methacrylate), and (methyl) acrylate-based " (meth) acryloxy " (methyl) acryloxy that is otherwise known as.
Photosensitive resin composition of the present invention, comprises alkali soluble resin, containing compound, light trigger, the organic solvent of ethene unsaturated group, and pigment.
Wherein, this alkali soluble resin comprises the first alkali soluble resin, this first alkali soluble resin is to have containing the first unsaturated monomer of carboxylic acid group, containing the second unsaturated monomer of aromatic ring structure, and containing the polymeric reaction product of the potpourri of the 3rd unsaturated monomer of alicyclic structure, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.40.
If the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is less than 0.01, this photosensitive resin composition is in the time of exposure, developing manufacture process, have the poor problem of developability, if the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is greater than 0.40, this liquid crystal indicator has blister display defect problem.Preferably, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.35; More preferably, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.30.
Thus, manufacture in the process of colored filter of the present invention at this photosensitive resin composition of use, this photosensitive resin composition is when through exposure, developing manufacture process, have preferably developability, and this photosensitive resin composition after via lithographic process, can form the pixel dyed layer with splendid resistance to sputter, further, in the time using this colored filter to produce liquid crystal indicator of the present invention, can make this liquid crystal indicator completely without blister display defect.
So-called this first unsaturated monomer is selected from acrylic acid, methacrylic acid, 2-methacryl ethoxy succinate, butenoic acid, α-chloroacrylic acid, ethylacrylic acid, cinnamic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, or these a combination.Preferably, this first unsaturated monomer is to be selected from acrylic acid, methacrylic acid, 2-methacryl ethoxy succinate, or these a combination.
Taking this mixture total weight as 100 weight portions, the content of this first unsaturated monomer is between 20 weight portion～60 weight portions, again with 22 weight portion～58 weight portions for better, make this photosensitive resin composition exposing, when the lithographic process such as development, have preferably developability.
So-called this second unsaturated monomer is selected from styrene, α-methyl styrene, vinyltoluene, to chlorostyrene, divinylbenzene, benzyl methacrylate, benzyl acrylate, phenyl methyl acrylate, phenyl acrylate, 2-nitrobenzophenone acrylate, 4-nitrobenzophenone acrylate, 2-nitrobenzene methyl acrylate, 2-nitrobenzoyl ylmethyl acrylate, 2-nitrobenzophenone methacrylate, 2-Chlorophenylmethyl acrylate, 4-Chlorophenylmethyl acrylate, 2-chlorphenyl acrylate, 4-chlorphenyl acrylate, phenoxy group ethyl-methyl acrylate, phenoxy group polyethylene glycol acrylate, phenoxy group polyethylene glycol methacrylate-styrene polymer, Nonylphenoxy polyethylene glycol acrylate, Nonylphenoxy polyethylene glycol methacrylate-styrene polymer, nitrogen-phenyl maleimide, nitrogen-o-hydroxy phenyl maleimide, nitrogen-m-hydroxy phenyl maleimide, nitrogen-p-hydroxy phenyl maleimide, nitrogen-o-aminomethyl phenyl maleimide, nitrogen-m-aminomethyl phenyl maleimide, nitrogen-p-aminomethyl phenyl maleimide, nitrogen-o-methoxyphenyl maleimide, nitrogen-m-methoxyphenyl maleimide, nitrogen-p-methoxyphenyl maleimide, o-vinylphenol, m-vinylphenol, p-vinylphenol, 2-methyl-4-Vinyl phenol, 3-methyl-4-Vinyl phenol, o-isopropenyl phenol, m-isopropenyl phenol, p-isopropenyl phenol, 2-vinyl-1-naphthols, 3-vinyl-1-naphthols, 1-vinyl-beta naphthal, 3-vinyl-beta naphthal, 2-isopropenyl-1-naphthols, 3-isopropenyl-1-naphthols, o-methoxy styrene, m-methoxy styrene, p-methoxystyrene, o-methoxy styrene, m-methoxy styrene, p-methoxy styrene, o-(vinyl benzene methyl) glycidyl ethers, m-(vinyl benzene methyl) glycidyl ethers, p-(vinyl benzene methyl) glycidyl ethers, indenes, acetyl group naphthalene, or these a combination.Wherein, this second unsaturated monomer with styrene, α-methyl styrene, phenyl methyl acrylate, phenyl acrylate, nitrogen-phenyl maleimide, nitrogen-o-hydroxy phenyl maleimide, nitrogen-m-hydroxy phenyl maleimide and nitrogen-p-hydroxy phenyl maleimide etc. for better.
Taking this mixture total weight as 100 weight portions, the content of this second unsaturated monomer is between 0.5 weight portion～20 weight portion, be preferably 0.8 weight portion～18 weight portion, can make this photosensitive resin composition after via lithographic process, the pixel dyed layer forming can present splendid resistance to sputter.
The 3rd unsaturated monomer be selected from there is dicyclo pentyl group (dicyclopentanyl group) unsaturated compound, there is the unsaturated compound of double cyclopentenyl group (dicyclopentenyl group) or these a combination.
Specifically, the 3rd unsaturated monomer can be dicyclo amyl group acrylate, dicyclo amyl group ethoxy propylene acid esters, double cyclopentenyl acrylate, double cyclopentenyl ethoxy propylene acid esters, dicyclo amyl group methacrylate, dicyclo amyl group ethoxyl methyl acrylate, double cyclopentenyl methacrylate, double cyclopentenyl ethoxyl methyl acrylate, or these a combination.
In these mixture total weight 100 weight portions, the content of the 3rd unsaturated monomer, between 20 weight portion～50 weight portions, can make the pixel dyed layer of this colored filter in order to form have splendid resistance to sputter.
Preferably, the content summation of this second unsaturated monomer and the 3rd unsaturated monomer, between 25 weight portion～60 weight portions, can be used the pixel dyed layer of this colored filter to form to have splendid resistance to sputter.
Generate this potpourri of this first alkali soluble resin in order to polyreaction, also there is the 4th unsaturated monomer.
So-called the 4th unsaturated monomer is selected from nitrogen-N-cyclohexylmaleimide, methyl acrylate, ethyl acrylate, acrylic acid n-propyl, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, tert-butyl acrylate, acrylic acid 2-hydroxy methacrylate, acrylic acid 2-hydroxy propyl ester, acrylic acid 3-hydroxy propyl ester, acrylic acid 2-hydroxyl butyl ester, acrylic acid 3-hydroxyl butyl ester, acrylic acid 4-hydroxyl butyl ester, allyl acrylate, acrylic acid triethylene glycol methoxyethoxy ester, nitrogen, nitrogen-dimethylamino ethyl acrylate, nitrogen, nitrogen-diethylamino propyl acrylate, nitrogen, nitrogen-dibutylamino propyl acrylate, acrylic acid epoxy propyl diester, methyl methacrylate, β-dimethyl-aminoethylmethacrylate, n propyl methacrylate, isopropyl methacrylate, n-BMA, isobutyl methacrylate, the secondary butyl ester of methacrylic acid, Tert-butyl Methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxy propyl ester, methacrylic acid 3-hydroxy propyl ester, methacrylic acid 2-hydroxyl butyl ester, methacrylic acid 3-hydroxyl butyl ester, methacrylic acid 4-hydroxyl butyl ester, allyl methacrylate, methacrylic acid triethylene glycol methoxyethoxy ester, lauryl methacrylate, methacrylic acid myristyl ester, methacrylic acid cetyl ester, methacrylic acid stearyl, methacrylic acid eicosyl ester, methacrylic acid docosyl ester, methacrylic acid nitrogen, nitrogen-dimethylamino ethyl ester, nitrogen, nitrogen-dimethylaminomethyl propyl acrylate, nitrogen-iso-butyl amino methyl ethyl acrylate, methacrylic acid glycidyl ester, vinyl acetate, propionate, vinyl butyrate, methoxy ethylene, ethyl vinyl ether, allyl glycidyl ethers, methylallyl glycidyl ethers (methallyl glycidyl ether), vinyl cyanide, methacrylonitrile, α-chloro-acrylonitrile, the sub-ethene of cyaniding, acrylamide, Methacrylamide, α-chloropropene acid amides, nitrogen-hydroxyethyl acrylamide, nitrogen-hydroxyethyl methacrylamide, 1,3-butadiene, isopentene, chlorination butadiene, or these a combination, wherein again with methyl acrylate, ethyl acrylate, acrylic acid n-propyl, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, tert-butyl acrylate, acrylic acid 2-hydroxy methacrylate, acrylic acid 2-hydroxy propyl ester, methyl methacrylate, β-dimethyl-aminoethylmethacrylate, n propyl methacrylate, isopropyl methacrylate, n-BMA, isobutyl methacrylate, the secondary butyl ester of methacrylic acid, Tert-butyl Methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxy propyl ester, methacrylic acid glycidyl ester, vinyl acetate, vinyl cyanide, methacrylonitrile, 1,3-butadiene, isopentene is for better.
Taking this mixture total weight as 100 weight portions, the content of the 4th unsaturated monomer between 0 weight portion～15 weight portion, again with 0 weight portion～12 weight portion for better, can make the developability of this photosensitive resin composition better.
Taking this alkali soluble resin gross weight as 100 weight portions, the content of this first alkali soluble resin, between 30 weight portion～90 weight portions, is preferably 35 weight portion～85 weight portions, can allow this liquid crystal indicator completely without blister display defect.
This alkali soluble resin also comprises the second alkali soluble resin, and this second alkali soluble resin comprises the monomer of (1) structure that has formula:
formula (1)
In formula (1), R 1and R 2represent respectively hydrogen atom, C 1～C 5straight or branched alkyl, phenyl, or halogen atom.
This monomer with formula (1) structure is by the compound that contains formula (1) structure, obtains with other copolymerizable compound reactions of reacting.
Wherein, the described compound that contains formula (1) structure, can be bisphenol fluorene (bisphenol fluorene) the type compound containing epoxy radicals (epoxy) shown in formula (1-1), or the bisphenol fluorene type compound of hydroxyl (hydroxy) shown in formula (1-2).
formula (1-1)
In formula (1-1), R 3r with formula (1) 1identical, R 4r with formula (1) 2identical.
formula (1-2)
In formula (1-2), R 5r with formula (1) 1identical, R 6r with formula (1) 2identical; R 7and R 8represent respectively C 1～C 20alkylidene or sub-alicyclic group; K, l are respectively the integer between 1～4.
And the compound of other copolymerizable reactions of indication can be enumerated as unsaturated monocarboxylic acid classes such as acrylic acid, methacrylic acid, butenoic acid, α-chloroacrylic acid, ethylacrylic acid, cinnamic acids; Dicarboxylic acids class and the acid anhydrides thereof such as maleic acid, itaconic acid, succinic acid, phthalic acid, tetrahydrobenzene dioctyl phthalate, hexahydrobenzene dioctyl phthalate, methyltetrahydro phthalic acid, methyl hexahydrobenzene dioctyl phthalate, methyl endo-methylene group tetrahydrobenzene dioctyl phthalate (methyl endo-methylene tetrahydro phthalic acid), chlorendic acid (chlorendic acid), glutaric acid; Tricarboxylic acid class and the acid anhydrides thereof such as 1,2,4-benzenetricarboxylic acid (trimellitic acid); And 1,2, quaternary carboxylic acids and the acid anhydrides thereof such as 4,5-benzene tetracarboxylic acid (pyromellitic acid), benzophenone tetrabasic carboxylic acid (benzophenone tetracarboxylic acid), two benzene tertacarbonic acid (biphenyl tetracarboxylic acid), two phenylate tetrabasic carboxylic acid (biphenylether tetracarboxylic acid).
More specifically, this second alkali soluble resin is Nippon Steel's chemistry system, and product are called the products such as V259ME, V301ME.
Taking this alkali soluble resin gross weight as 100 weight portions, the content of this second alkali soluble resin, between 10 weight portion～70 weight portions, is preferably 15～65 weight portions, can allow this liquid crystal indicator without blister display defect.
Should be selected from the first compound, the second compound containing the compound of ethene unsaturated group, or these a combination.
This first compound be reacted with (methyl) acrylic acid by the polyvalent alcohol through caprolactone upgrading and (methyl) acrylate based compound.
This polyvalent alcohol through caprolactone upgrading is to be made with having 4 more than functional group polyol reactions by this caprolactone, and wherein, this caprolactone can be γ-hexalactone, δ-caprolactone, or 6-caprolactone, and taking 6-caprolactone as good.This has 4 polyvalent alcohols more than functional group can be pentaerythrite, two-trimethylolpropane, dipentaerythritol etc.Preferably, taking this content with 4 polyvalent alcohols more than functional group as 1 mole, the content range of this caprolactone is 1～12 mole.
The concrete example of this first compound is as four (methyl) acrylic ester compound of pentaerythrite caprolactone upgrading, four (methyl) acrylic ester compound of two-trimethylolpropane caprolactone upgrading, many (methyl) acrylic ester compound of dipentaerythritol caprolactone upgrading etc., wherein, many (methyl) acrylic ester compound of this dipentaerythritol caprolactone upgrading can be two (methyl) acrylic ester compound of dipentaerythritol caprolactone upgrading, three (methyl) acrylic ester compound of dipentaerythritol caprolactone upgrading, four (methyl) acrylic ester compound of dipentaerythritol caprolactone upgrading, five (methyl) acrylic ester compound of dipentaerythritol caprolactone upgrading, six (methyl) acrylic ester compound of dipentaerythritol caprolactone upgrading etc.
Further, the structure of many (methyl) esters of acrylic acid of above-mentioned dipentaerythritol caprolactone upgrading can formula (2) represent:
formula (2)
In formula (2), R 9and R 10represent respectively hydrogen or methyl; M is 1～2 integer; A is 1～6 integer, the integer that b is 0～5, and wherein, a+b=2～6, are preferably a+b=3～6, are more preferred from a+b=5～6, and the best is a+b=6.
More specifically, this first compound is Nippon Kayaku K. K's system, the name of an article the products such as DPCA-20, DPCA-30, DPCA-60, DPCA-120.
This second compound has suc as formula the functional group shown in (3).
formula (3)
In formula (3), R 11represent respectively hydrogen or methyl.
This second compound can be enumerated as acrylamide, (methyl) acryloyl morpholine, (methyl) acrylic acid-7-amino-3,7-dimethyl monooctyl ester, isobutoxy methyl (methyl) acrylamide, (methyl) acrylic acid isobornyl 2-ethoxyethyl acetate, (methyl) isobornyl acrylate, (methyl) acrylic acid-2-ethyl caproite, ethyl diglycol (methyl) acrylate, tertiary octyl group (methyl) acrylamide, two acetone (methyl) acrylamide, (methyl) acrylic acid dimethylamino ester, (methyl) dodecylacrylate, (methyl) acrylic acid two cyclopentene 2-ethoxyethyl acetates, (methyl) acrylic acid two cyclopentene esters, nitrogen, nitrogen-dimethyl (methyl) acrylamide, (methyl) acrylic acid tetrachloro phenyl ester, (methyl) acrylic acid-2-tetrachloro phenoxy ethyl, (methyl) tetrahydrofurfuryl acrylate, (methyl) tetrabromophenyl acrylate, (methyl) acrylic acid-2-tetrabromo phenoxy ethyl, (methyl) acrylic acid-2-Trichlorophenoxy ethyl ester, (methyl) tribromophenyl acrylate, (methyl) acrylic acid-2-tribromophenoxy ethyl ester, (methyl) acrylic acid-2-hydroxyl ethyl ester, (methyl) 2-hydroxypropyl acrylate, caprolactam, nitrogen-vinyl pyrrolidone, (methyl) acrylic acid phenoxy ethyl, (methyl) Pentachlorophenyl Acrylate, (methyl) acrylic acid pentabromo-phenyl ester, poly-single (methyl) acrylic acid glycol ester, poly-single (methyl) acrylic acid propylene glycol ester, (methyl) acrylic acid norbornene ester, ethylene glycol bisthioglycolate (methyl) acrylate, two (methyl) acrylic acid, two cyclopentene esters, triethylene glycol diacrylate, tetraethylene glycol two (methyl) acrylate, three (2-hydroxyethyl) isocyanates two (methyl) acrylate, three (2-hydroxyethyl) isocyanates three (methyl) acrylate, three (2-hydroxyethyl) isocyanates three (methyl) acrylate of caprolactone upgrading, three (methyl) acrylic acid trihydroxy methyl propyl ester, three (methyl) acrylic acid trihydroxy methyl propyl ester of oxirane (hereinafter to be referred as EO) upgrading, three (methyl) acrylic acid trihydroxy methyl propyl ester of epoxypropane (hereinafter to be referred as PO) upgrading, triethylene glycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, BDO two (methyl) acrylate, 1,6-hexanediol two (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, polyester two (methyl) acrylate, polyglycol two (methyl) acrylate, dipentaerythritol six (methyl) acrylate, dipentaerythritol five (methyl) acrylate, dipentaerythritol four (methyl) acrylate, dipentaerythritol six (methyl) acrylate of caprolactone upgrading, dipentaerythritol five (methyl) acrylate of caprolactone upgrading, four (methyl) acrylic acid, two trihydroxy methyl propyl ester, bisphenol-A two (methyl) acrylate of EO upgrading, bisphenol-A two (methyl) acrylate of PO upgrading, hydrogenated bisphenol A two (methyl) acrylate of EO upgrading, hydrogenated bisphenol A two (methyl) acrylate of PO upgrading, the glycerin tripropionate of PO upgrading, Bisphenol F two (methyl) acrylate of EO upgrading, phenolic aldehyde polyglycidyl ether (methyl) acrylate etc.
Preferably, this second compound is selected from the dipentaerythritol acrylate, tetrapropylene acid two trihydroxy methyl propyl ester, the glycerin tripropionate of PO upgrading, the TO-1382 processed of Japanese Toagosei Co., Ltd of three acrylic acid trihydroxy methyl propyl ester, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, dipentaerythritol acrylate, dipentaerythritol five acrylate, dipentaerythritol tetraacrylate, the caprolactone upgrading of three acrylic acid trihydroxy methyl propyl ester, the PO upgrading of three acrylic acid trihydroxy methyl propyl ester, EO upgrading, or these a combination.
Taking this alkali soluble resin gross weight as 100 weight portions, the content of this first compound is between 35 weight portion～100 weight portions, be preferably 38 weight portion～95 weight portions, be more preferred from 40 weight portion～90 weight portions, by the caprolactone structure of this first compound, can allow this liquid crystal indicator compared with non-foam display defect.
Taking this alkali soluble resin gross weight as 100 weight portions, the content of this second compound is between 45 weight portion～90 weight portions, be preferably 48 weight portion～85 weight portions, be more preferred from 50 weight portion～80 weight portions, to allow this photosensitive resin composition present excellent developability.
Taking this alkali soluble resin gross weight as 100 weight portions, should be containing the content of the compound of ethene unsaturated group between 10 weight portion～500 weight portions, better with 20 weight portion～450 weight portions, better with 30 weight portion～400 weight portions again, can allow this photosensitive resin composition there is good developability.
This light trigger of the present invention, can be selected from acetophenone based compound (acetophenone), diimidazole based compound (biimidazole), acyl oxime compound (acyl oxime), or these a combination.
The acetophenone based compound of indication as: to dimethylamino acetophenone (p-dimethylamino-acetophenone), α, α '-dimethoxy azoxy acetophenone (α, α '-dimethoxyazoxy-acetophenone), 2, 2 '-dimethyl-2-phenyl acetophenone (2, 2 '-dimethyl-2-phenyl-acetophenone), acetanisole (p-methoxy-acetophenone), 2-methyl isophthalic acid-(4-methyl thio-phenyl)-2-morpholino-1-acetone [2-methyl-1-(4-methylthiophenyl)-2-morpholino-1-propanone], 2-benzyl-2-nitrogen, nitrogen-dimethylamino-1-(4-morpholino phenyl)-1-butanone [2-benzyl-2-N, N-dimethylamino-1-(4-morpholinophenyl)-1-butanone].
The diimidazole based compound of indication as: 2, 2 '-bis-(o-chlorphenyls)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bis (o-chlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(ortho-fluorophenyl bases)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bis (o-fluorophenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(o-aminomethyl phenyls)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bis (o-methyl phenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(o-methoxyphenyls)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bis (o-methoxyphenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(o-ethylphenyls)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bi s (o-ethylphenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(p-methoxyphenyl)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bi s (p-methoxyphenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(2, 2 ', 4, 4 '-tetramethoxy phenyl)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bis (2, 2 ', 4, 4 '-tetramethoxyphenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bi s (2-chlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole], 2, 2 '-bis-(2, 4-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl diimidazole [2, 2 '-bis (2, 4-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl-biimidazole] etc.
The acyl oxime compound of indication is as ethane ketone, 1-[9-ethyl-6-(2-methyl benzoyl)-9 hydrogen-carbazole-3-substituting group]-, 1-(oxygen-acetyl oxime) [Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-y1]-, 1-(O-acetyl oxime), CGI-242 person as by name in the product of Ciba Specialty Chemicals system, its structure is shown in shown in formula (4)], 1-(4-phenyl-sulfo--phenyl)-octane-1, 2-diketone 2-oxime-oxygen-benzoic ether [1-(4-phenyl-thio-phenyl)-octane-1, 2-dion 2-oxime-O-benzoate, CGI-124 person as by name in the product of Ciba Specialty Chemicals system, its structure is shown in shown in formula (5)], ethane ketone, 1-[9-ethyl-6-(the chloro-4-benzyl-sulfo--benzoyl of 2-)-9 hydrogen-carbazole-3-substituting group]-, 1-(oxygen-acetyl oxime) [Ethanone, 1-[9-ethyl-6-(2-cholro-4-benzyl-thio-benzoyl)-9H-carbazole-3-y1]-, 1-(O-acetyl oxime), rising sun electrification company system, its structure is shown in shown in formula (6)].
formula (4)
formula (5)
formula (6)
Preferably; this light trigger is 2-methyl isophthalic acid-(4-methyl thio-phenyl)-2-morpholino-1-acetone, 2-benzyl-2-nitrogen; nitrogen-dimethylamino-1-(4-morpholino phenyl)-1-butanone, 2; 2 '-bis-(o-chlorphenyl)-4,4 ', 5; 5 '-tetraphenyl diimidazole, ethane ketone; 1-[9-ethyl-6-(2-methyl benzoyl)-9 hydrogen-carbazole-3-substituting group]-, 1-(oxygen-acetyl oxime), or these a combination.
This light trigger of the present invention, can further add following compound: thioxanthones (thioxanthone), 2, 4-diethyl thioxanthone (2, 4-diethyl-thioxanthanone), thioxanthones-4-sulfone (thioxanthone-4-sulfone), benzophenone (benzophenone), 4, 4 '-bis-(dimethylamino) benzophenone [4, 4 '-bis (dimethylamino) benzophenone], 4, 4 '-bis-(lignocaine) benzophenone [4, 4 '-bis (diethylamino) benzophenone] etc. benzophenone (benzophenone) based compound, α-diketone (α-diketone) classes such as benzil (benzil), acetyl group (acetyl), keto-alcohol (acyloin) class of benzoin (benzoin) etc., keto-alcohol ether (acyloin ether) classes such as benzoin methylether (benzoin methylether), benzoin ethyl ether (benzoin ethylether), benzoin iso-propylether (benzoin isopropyl ether), 2,4,6-trimethylbenzene acyl group diphenyl phosphine oxide (2,4,6-trimethyl-benzoyl-diphenyl-phosphineoxide), two-(2,6-dimethoxy benzoyl group)-2,4,4-trimethyl benzyl base phosphine oxide [bis-(2,6-dimethoxy-benzoyl)-2,4,4-trimethyl-benzyl-phosphine oxide] etc. acylphosphine oxide (acylphosphineoxide) class, quinone (quinone) classes such as anthraquinone (anthraquinone), 1,4-naphthoquinone (Isosorbide-5-Nitrae-naphthoquinone), the halogenide such as chloroacetophenone (phenacyl chloride), trisbromomethyl benzene sulfone (tribromomethyl-phenylsulfone), three (trichloromethyl)-s-triazines [tris (trichloromethyl)-s-triazine], and the superoxide such as two-tert-butyl peroxide (di-tertbutylperoxide).Wherein, better with benzophenone (benzophenone) based compound, especially with 4,4 '-bis-(lignocaine) benzophenone is best.
Taking this alkali soluble resin gross weight as 100 weight portions, the content of this light trigger is between 2 weight portion～100 weight portions, is preferably 3 weight portion～75 weight portions, is more preferred from 5 weight portion～50 weight portions.
This organic solvent of the present invention can dissolve this alkali soluble resin, the compound that should contain ethene unsaturated group and this light trigger, and can not react with it, and have suitable volatility.
Concrete example that this organic solvent is commonly used is as ethylene glycol monomethyl ether, ethylene glycol ethyl ether, diethylene glycol methyl ether, DGDE, diglycol positive propyl ether, diglycol n-butyl ether, triethylene glycol methyl ether, triethylene glycol ether, propylene glycol monomethyl ether, propylene-glycol ethyl ether, dipropylene glycol methyl ether, dipropylene glycol ether, dipropylene glycol positive propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol monomethyl ether (tripropylene glycol mono methyl ether), (gathering) alkylene glycol mono alkane ethers of tripropylene glycol list ether (tripropylene glycol mono ethyl ether) etc., (gathering) alkylene glycol mono alkane ether acetate classes such as glycol methyl ether acetate, ethylene glycol ether acetate, 1-Methoxy-2-propyl acetate, propylene-glycol ethyl ether acetate, other ethers such as diethylene glycol dimethyl ether, diglycol ethyl methyl ether, diethyl carbitol, tetrahydrofuran, the ketones such as MEK, cyclohexanone, 2-HEPTANONE, 3-heptanone, the lactic acid alkane ester classes such as 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl methyl propionate, 2-hydroxy-2-methyl ethyl propionate, 3-methoxy methyl propionate, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, ethoxy ethyl acetate, hydroxyl ethyl acetate, 2-hydroxy-3-methyl methyl butyrate, 3-methyl-3-methoxyl butylacetic acid ester, 3-methyl-3-methoxyl butyl propionic ester, ethyl acetate, n-butyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl acetate, isoamyl acetate, n-butyl propionate, ethyl butyrate, propyl butyrate, isopropyl isobutyrate, the positive butyl ester of butyric acid, methyl pyruvate, ethyl pyruvate, pyruvic acid n-propyl, methyl acetoacetate, ethyl acetoacetate, other ester classes such as 2-oxygen base ethyl butyrate, the aromatic hydrocarbons such as toluene, dimethylbenzene class, and n-methlpyrrolidone, nitrogen, nitrogen-dimethyl formamide, nitrogen, the carboxylic acyloxy amines such as nitrogen-dimethyl acetamide etc.
Preferably, this organic solvent is to select a use or mix with 1-Methoxy-2-propyl acetate, 3-ethoxyl ethyl propionate to use.
Taking this alkali soluble resin gross weight as 100 weight portions, the content of this organic solvent, between 500 weight portion～5000 weight portions, is preferably 800 weight portion～4000 weight portions.
This pigment can be inorganic pigment, organic pigment, or these a combination.
Described inorganic pigment is that metal oxide, metal coordinate the metallic compounds such as salt, and concrete example is as the oxide of the metals such as iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, sub-lead, antimony, and the composite oxides of aforementioned metal.
Described organic pigment, can select one and use separately or mix multiple use by not enumerating below: C.I. pigment yellow 1,3,11,12,13,14,15,16,17 in person, 20,24,31,53,55,60,61,65,71,73,74,81,83,93,95,97,98,99,100,101,104,106,108,109,110,113,114,116,117,119,120,126,127,128,129,138,139,150,151,152,153,154,155,156,166,167,168,175, C.I. pigment orange 1,5,13,14,16,17,24,34,36,38,40,43,46,49,51,61,63,64,71,73, C.I. paratonere 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 30, 31, 32, 37, 38, 40, 41, 42, 48:1, 48:2, 48:3, 48:4, 49:1, 49:2, 50:1, 52:1, 53:1, 57, 57:1, 57:2, 58:2, 58:4, 60:1, 63:1, 63:2, 64:1, 81:1, 83, 88, 90:1, 97, 101, 102, 104, 105, 106, 108, 112, 113, 114, 122, 123, 144, 146, 149, 150, 151, 155, 166, 168, 170, 171, 172, 174, 175, 176, 177, 178, 179, 180, 185, 187, 188, 190, 193, 194, 202, 206, 207, 208, 209, 215, 216, 220, 224, 226, 242, 243, 245, 254, 255, 264, 265, C.I. pigment violet 1,19,23,29,32,36,38,39, C.I. pigment blue 1,2,15,15:3,15:4,15:6,16,22,60,66, C.I. pigment Green 7,36,37, C.I. pigment brown 23,25,28, and C.I. pigment black 1,7.
The mean grain size of the primary particle of this pigment is preferably 10nm～200nm, is more preferred from 20nm～150nm, and the best is 30nm～130nm.
If desired, this pigment (E) also can be followed use spreading agent, for example: the surfactants such as kation system, negative ion system, nonionic system, both sexes, polysiloxane series, fluorine system.
Described surfactant can be selected one and uses separately or mix multiple use from do not enumerate below person: the polyethylene oxide alkyl ethers classes such as polyethylene oxide lauryl ether, polyethylene oxide stearoyl ether, polyethylene oxide oil ether; The polyethylene oxide alkyl benzene ethers such as polyethylene oxide octyl group phenylate, polyethylene oxide nonyl phenylate; The polyethylene glycol di such as polyethylene glycol dilaurate, polyglycol distearate class; Sorbitan fatty acid ester class; The polyesters of fatty acid upgrading; The polyurethane class of tertiary amine upgrading; Puli's furlong (Polyflow) product of the KP product of SHIN-ETSU HANTOTAI's chemical industry system, the SF-8427 product of Toray Dow Corning Silicon system, common prosperity society oil chemical industry system, Ai Fuduopu (F-Top) product of get Ke Mu company system (Tochem Products Co., Ltd.), large Japan print Mei Kafuke (Megafac) product of black chemical industry system, Fu Luoduo (Fluorade) product of Sumitomo 3M system, A Sakaduo (Asahi Guard) product of Asahi Glass system, Sa Fulong (Surflon) product of Asahi Glass system.
Taking this alkali soluble resin gross weight as 100 weight portions, the content of this pigment, between 100 weight portion～500 weight portions, is preferably 120 weight portion～450 weight portions.Photosensitive resin composition of the present invention, be with aforementioned this alkali soluble resin, be somebody's turn to do compound, this light trigger, this organic solvent containing ethene unsaturated group, and this pigment is neccessary composition, for example, and visual demand further adds additive: surfactant, filling agent, macromolecular compound (referring to that this alkali soluble resin is with epigenesist), adherence promoter, antioxidant, ultraviolet light absorber, anti-agglutinant etc.
Wherein, described surfactant can improve coating of the present invention, and its concrete example is as the surfactant person of use that aforementioned this pigment is followed; Taking this alkali soluble resin gross weight as 100 weight portions, the content of this surfactant is between 0 weight portion～6 weight portion, is preferably 0 weight portion～4 weight portion, is more preferred from 0 weight portion～3 weight portion.
Moreover this filling agent can be glass, aluminium, this macromolecular compound can be polyvinyl alcohol (PVA), polyalkylene glycol monoalkyl ether, poly-perfluoroalkyl acrylate alkane ester, this adherence promoter can be vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxyethoxy) silane, nitrogen-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, nitrogen-(2-amino-ethyl)-3-TSL 8330, APTES, 3-epoxy prapanol propyl trimethoxy silicane, 3-epoxy prapanol propyl group methyl dimethoxysilane, 2-(3, 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-metacryloxy propyl trimethoxy silicane, 3-mercapto propyl trimethoxy silicane, this antioxidant can be 2,2-thiobis (4-methyl-6-tert-butylphenol), 2,6-bis--tert-butyl phenol, this ultraviolet light absorber can be 2-(the 3-tert-butyl group-5-methyl-2-hydroxy phenyl)-5-chlorphenyl nitrine, alkoxy benzophenone, this anti-agglutinant can be sodium polyacrylate.
In these alkali soluble resin gross weight 100 weight portions, the content of the additives such as macromolecular compound beyond described filling agent, this alkali soluble resin, adherence promoter, antioxidant, ultraviolet light absorber, anti-agglutinant is between 0 weight portion～10 weight portion, be preferably 0 weight portion～6 weight portion, be more preferred from 0 weight portion～3 weight portion.
The preparation of photosensitive resin constituent of the present invention, compound and this light trigger etc. that makes this alkali soluble resin, should contain ethene unsaturated group, mix, be dissolved in this organic solvent after, add again this pigment, separately be added into if desired the additive such as surfactant, adherence promoter, to give even mixing, just adjustable this photosensitive resin constituent that is solution state that makes.
Colored filter of the present invention, comprises the pixel dyed layer being formed after photoetching treatment by this photosensitive resin composition.
In the time that the making of carrying out this colored filter is shaped, be by revolution be coated with, curtain coating is coated with or the coating method such as print roll coating, the above-mentioned photosensitive resin constituent of the present invention that is solution state is coated on substrate.This substrate can be for the alkali-free glass of liquid crystal indicator, soda-lime glass, hard glass (Pai Lesi glass), quartz glass, and be attached with these glass of nesa coating, or for the substrate (as: silicon substrate) of photo-electric conversion device (as solid-state image sensor); And, before this photosensitive resin constituent is coated on this substrate, be that the black matrix" for shading (black matrix) that first can isolate the pixel dyed layers such as red, green, blue shapes on this substrate.
After coating, first remove the contained most organic solvent of this photosensitive resin constituent in drying under reduced pressure mode, then in pre-baked (pre-bake) mode, remaining organic solvent is removed completely, make it form pre-baked film.In process, drying under reduced pressure and pre-baked operating conditions are according to the kind of each composition, coordinate ratio and difference, conventionally, drying under reduced pressure is under the pressure of 0mmHg～200mmHg, to carry out for 1 second～60 second, and pre-baked be to carry out 1 minute～15 minutes at 70 DEG C～110 DEG C temperature.
After pre-baked, with the mask with specific pattern, this pre-baked film is exposed.The light using in exposure process, taking ultraviolet rays such as g line, b line, i lines as good, and can be (surpassing) high-pressure mercury-vapor lamp and metal halid lamp in order to send ultraviolet equipment.
After exposure, this pre-baked film be impregnated in to temperature in the developer solution of 23 ± 2 DEG C, carry out the development of approximately 15 seconds～5 minutes, remove the unwanted part of this pre-baked film, to form predetermined pattern on this substrate.
The developer solution using can be by NaOH, potassium hydroxide, sodium carbonate, sodium bicarbonate, sal tartari, saleratus, sodium silicate, sodium methyl silicate, ammoniacal liquor, ethamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrroles, croak pyridine, or 1, 8-diazabicylo-(5, 4, 0)-alkaline aqueous solution that the alkali compounds such as 7-hendecene form, its concentration is generally between 0.001 % by weight～10 % by weight, be preferably between 0.005 % by weight～5 % by weight, be more preferred between 0.01 % by weight～1 % by weight.
Afterwards, water is cleaned the pattern on this substrate, again with pressurized air or compressed nitrogen by air-dry this pattern, finally with the heating arrangement such as hot plate or baking oven, this pattern is carried out to rear heat treated (post-bake), heating-up temperature is set between 150 DEG C～250 DEG C, heat time while using hot plate is 5 minutes～60 minutes, and the heat time while using baking oven is 15 minutes～150 minutes, so as to making this pattern fix, be configured as a pixel dyed layer.
Repeat above-mentioned steps, the pixel dyed layers such as red, green, blue just can sequentially be shaped on this substrate.
Then, in temperature under the vacuum environment between 220 DEG C～250 DEG C, in the surperficial sputter shaping ITO diaphragm of described pixel dyed layer; if desired; this ITO diaphragm is implemented to etching and wiring, then in this ITO diaphragm surface-coated alignment film, just can make and be shaped this colored filter.
Liquid crystal indicator of the present invention, comprises this colored filter.
Further, simply with regard to the manufacture of this liquid crystal indicator (as liquid crystal panel), separately get and be inlaid with thin film transistor (TFT) (Thin Film Transistor, TFT) and be coated with the glass substrate of alignment film, between aforementioned this colored filter and this glass substrate, get involved gap and do subtend configuration, inject liquid crystal molecule in this gap again, respectively at the outside surface laminating Polarizer of this colored filter and this glass substrate, can make this liquid crystal indicator subsequently.
The present invention will be described further with regard to following examples, but will be appreciated that, illustrated embodiment is the use for illustrating only, and should not be interpreted as restriction of the invention process.
[synthesis example 1 to 12 of the first alkali soluble resin]
On four cervical vertebra bottles of 1000 milliliters of volumes, nitrogen inlet, stirrer, well heater, condenser pipe and thermometer are set, and according to the kind of composition shown in table 1 and use amount ratio, prepare the compositions such as first unsaturated monomer required in order to synthetic this alkali soluble resin, the second unsaturated monomer, the 3rd unsaturated monomer, the 4th unsaturated monomer, polymerization initiating agent and solvent.
While carrying out polymerization, first the continuous addings such as this first unsaturated monomer, this second unsaturated monomer, the 3rd unsaturated monomer and the 4th unsaturated monomer are entered in this four cervical vertebras bottle, and give and being uniformly mixed, the oil bath temperature of this four cervical vertebras bottle is promoted to 100 DEG C simultaneously; Separately this initiating agent is dissolved in this solvent, and gives and be divided into five aliquot, added an aliquot in this four cervical vertebras bottle at interval of one hour.The temperature of reaction of whole polymerization process maintains 100 DEG C, and polymerization time continues 6 hours, after polymerization completes, polymerizate is taken out in this four cervical vertebras bottle, and solvent devolatilization, just can this first alkali soluble resin.
[embodiment 1 to 8 of photosensitive resin composition, with comparative example 1 to 8]
According to the kind of composition shown in table 2 and use amount ratio, prepare the alkali soluble resin (comprise first alkali soluble resin and second alkali soluble resin) required in order to synthetic this photosensitive resin composition, contain the composition such as compound (comprising this first compound and the second compound), light trigger, organic solvent and pigment of ethene unsaturated group.
This alkali soluble resin, this compound, this light trigger and this pigment containing ethene unsaturated group were added after this organic solvent, dissolved mixing by swing-out stirrer, can modulate to obtain this photosensitive resin composition, carry out characteristic measurement with evaluation method described later again, gained evaluation result is as shown in table 2.
[evaluation method]
One, resistance to sputter
Utilize this photosensitive resin composition of modulating, on glass substrate, form pixel dyed layer, then sputter formed film resistance is that 14.6 Ω/sq, thickness are on this pixel dyed layer ito thin film, sputter temperature is 220 DEG C, to make this colored filter.Then, utilize the optical microscope of 100 times to observe respectively the surface appearance of the pixel dyed layer such as red, blue, green of this colored filter, and evaluate according to following standard:
Zero: flawless or scratch
△: a little slight crack and galled spots
×: slight crack and galled spots are a lot
Two, blister display defect
To use the prepared liquid crystal indicator of this colored filter, be placed in the environment of 100 DEG C of temperature, humidity 95RH%, the time t1 occurring with visual inspection blister display defect, and evaluate according to following standard:
◎: t1 > 500 hours
Zero: 300 hour < t1≤500 hour
△: 100 hours < t1≤300 hour
×: t1 < 100 hours
Three, developability (or claiming developing powder)
By the photosensitive resin composition of modulating, be coated in the mode of rotary coating on the glass substrate of 100mm × 100mm, first carrying out pressure is that 100mmHg, time are the drying under reduced pressure in 30 seconds, carry out temperature again and be 80 DEG C, time and be 3 minutes pre-baked, making it form thickness is the pre-baked film of 1.0 μ m.
Then, get 2 % by weight potassium hydroxide aqueous solution 2ml, drop on this pre-baked film, measure this pre-baked film and dissolve required time t2, be equivalent to development time, and evaluate according to following standard:
Zero: t2≤10 second
×: t2 > 10 seconds
[interpretation of result]
As can be known from the results of Table 2, as embodiment 1～8, taking this alkali soluble resin gross weight as 100 weight portions, at the operating weight of this first alkali soluble resin between 30～90 weight portions, and taking this first～four mixture total weight that unsaturated monomer is formed as 100 weight portions, the operating weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer, operating weight summation is respectively between 0.01～0.40, between 25～60 weight portions, the photosensitive resin composition of modulating is in the process of the pixel dyed layer in order to the colored filter that is shaped, it can present quite excellent resistance to sputter and developability really, simultaneously, the liquid crystal indicator being made into this colored filter, can not produce blister display defect completely yet.
Relatively, as comparative example 2～5, the first alkali soluble resin (being synthesis example 7～9) using, the operating weight ratio of its second unsaturated monomer and the 3rd unsaturated monomer is greater than 0.40, for another example comparative example 1, 7, 8, the first alkali soluble resin (being synthesis example 10～12) using, the operating weight ratio of its second unsaturated monomer and the 3rd unsaturated monomer is less than 0.01, and do not contain the second unsaturated monomer or the 3rd unsaturated monomer, the photosensitive resin composition of modulating is in the process of the pixel dyed layer in order to the colored filter that is shaped, poor in performances such as resistance to sputter and developability, simultaneously, the liquid crystal indicator of manufacturing with this colored filter, more can produce more serious blister display defect.
In sum, photosensitive resin composition of the present invention and use its colored filter and liquid crystal indicator, the first alkali soluble resin using by controlling this photosensitive resin composition, the weight ratio of its this second unsaturated monomer and the 3rd unsaturated monomer is the mode between 0.01～0.40, allow this photosensitive resin composition can present splendid developability in lithographic process, and the pixel dyed layer that allows this photosensitive resin composition of use of this colored filter form can present splendid resistance to sputter, allow simultaneously and use the prepared liquid crystal indicator of this colored filter completely without blister display defect.

Claims (17)

1. a photosensitive resin composition, comprises alkali soluble resin, containing compound, light trigger, the organic solvent of ethene unsaturated group, and pigment; It is characterized in that,
This alkali soluble resin comprises the first alkali soluble resin, this first alkali soluble resin is to have containing the first unsaturated monomer of carboxylic acid group, containing the second unsaturated monomer of aromatic ring structure, and containing the polymeric reaction product of the potpourri of the 3rd unsaturated monomer of alicyclic structure, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.40; This alkali soluble resin also comprises the second alkali soluble resin, and this second alkali soluble resin comprises the monomer of (1) structure that has formula:
In formula, R 1and R 2represent respectively hydrogen atom, C 1～C 5alkyl, the phenyl of straight or branched, or halogen atom;
Should be selected from the first compound containing the compound of ethene unsaturated group, or the combination of the first compound and the second compound, this first compound is reacted and obtains with (methyl) acrylic acid by the polyvalent alcohol of caprolactone upgrading; This second compound has suc as formula functional group shown in (3),
In formula, R 11represent respectively hydrogen or methyl.
2. photosensitive resin composition according to claim 1, is characterized in that, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.35.
3. photosensitive resin composition according to claim 1, is characterized in that, the weight ratio of this second unsaturated monomer and the 3rd unsaturated monomer is between 0.01～0.30.
4. photosensitive resin composition according to claim 1, is characterized in that, taking this mixture total weight as 100 weight portions, the content summation of this second unsaturated monomer and the 3rd unsaturated monomer is between 25 weight portion～60 weight portions.
5. photosensitive resin composition according to claim 1, it is characterized in that, this first unsaturated monomer is selected from acrylic acid, methacrylic acid, 2-methacryl ethoxy succinate, butenoic acid, α-chloroacrylic acid, ethylacrylic acid, cinnamic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, or these a combination.
6. photosensitive resin composition according to claim 1, is characterized in that, this second unsaturated monomer is selected from styrene, α-methyl styrene, vinyltoluene, to chlorostyrene, divinylbenzene, benzyl methacrylate, benzyl acrylate, phenyl methyl acrylate, phenyl acrylate, 2-nitrobenzophenone acrylate, 4-nitrobenzophenone acrylate, 2-nitrobenzene methyl acrylate, 2-nitrobenzoyl ylmethyl acrylate, 2-nitrobenzophenone methacrylate, 2-Chlorophenylmethyl acrylate, 4-Chlorophenylmethyl acrylate, 2-chlorphenyl acrylate, 4-chlorphenyl acrylate, phenoxy group ethyl-methyl acrylate, phenoxy group polyethylene glycol acrylate, phenoxy group polyethylene glycol methacrylate-styrene polymer, Nonylphenoxy polyethylene glycol acrylate, Nonylphenoxy polyethylene glycol methacrylate-styrene polymer, nitrogen-phenyl maleimide, nitrogen-o-hydroxy phenyl maleimide, nitrogen-m-hydroxy phenyl maleimide, nitrogen-p-hydroxy phenyl maleimide, nitrogen-o-aminomethyl phenyl maleimide, nitrogen-m-aminomethyl phenyl maleimide, nitrogen-p-aminomethyl phenyl maleimide, nitrogen-o-methoxyphenyl maleimide, nitrogen-m-methoxyphenyl maleimide, nitrogen-p-methoxyphenyl maleimide, o-vinylphenol, m-vinylphenol, p-vinylphenol, 2-methyl-4-Vinyl phenol, 3-methyl-4-Vinyl phenol, o-isopropenyl phenol, m-isopropenyl phenol, p-isopropenyl phenol, 2-vinyl-1-naphthols, 3-vinyl-1-naphthols, 1-vinyl-beta naphthal, 3-vinyl-beta naphthal, 2-isopropenyl-1-naphthols, 3-isopropenyl-1-naphthols, o-methoxy styrene, m-methoxy styrene, p-methoxystyrene, o-methoxy styrene, m-methoxy styrene, p-methoxy styrene, o-(vinyl benzene methyl) glycidyl ethers, m-(vinyl benzene methyl) glycidyl ethers, p-(vinyl benzene methyl) glycidyl ethers, indenes, acetyl group naphthalene, or these a combination.
7. photosensitive resin composition according to claim 1, is characterized in that, the 3rd unsaturated monomer be selected from have dicyclo amyl group unsaturated compound, there is the unsaturated compound of double cyclopentenyl or these a combination.
8. photosensitive resin composition according to claim 7, it is characterized in that, the 3rd unsaturated monomer is selected from (methyl) acrylic acid dicyclo pentyl ester, (methyl) acrylic acid dicyclo amyl group oxidation ethyl ester, (methyl) acrylic acid dicyclopentenyloxyethyl methacrylate, (methyl) acrylic acid dicyclo amylene oxidation ethyl ester, or these a combination.
9. photosensitive resin composition according to claim 1, is characterized in that, this potpourri also has the 4th unsaturated monomer.
10. photosensitive resin composition according to claim 9, is characterized in that, the 4th unsaturated monomer is selected from nitrogen-N-cyclohexylmaleimide, methyl acrylate, ethyl acrylate, acrylic acid n-propyl, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, tert-butyl acrylate, acrylic acid 2-hydroxy methacrylate, acrylic acid 2-hydroxy propyl ester, acrylic acid 3-hydroxy propyl ester, acrylic acid 2-hydroxyl butyl ester, acrylic acid 3-hydroxyl butyl ester, acrylic acid 4-hydroxyl butyl ester, allyl acrylate, acrylic acid triethylene glycol methoxyethoxy ester, nitrogen, nitrogen-dimethylamino ethyl acrylate, nitrogen, nitrogen-diethylamino propyl acrylate, nitrogen, nitrogen-dibutylamino propyl acrylate, acrylic acid epoxy propyl diester, methyl methacrylate, β-dimethyl-aminoethylmethacrylate, n propyl methacrylate, isopropyl methacrylate, n-BMA, isobutyl methacrylate, the secondary butyl ester of methacrylic acid, Tert-butyl Methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxy propyl ester, methacrylic acid 3-hydroxy propyl ester, methacrylic acid 2-hydroxyl butyl ester, methacrylic acid 3-hydroxyl butyl ester, methacrylic acid 4-hydroxyl butyl ester, allyl methacrylate, methacrylic acid triethylene glycol methoxyethoxy ester, lauryl methacrylate, methacrylic acid myristyl ester, methacrylic acid cetyl ester, methacrylic acid stearyl, methacrylic acid eicosyl ester, methacrylic acid docosyl ester, methacrylic acid nitrogen, nitrogen-dimethylamino ethyl ester, nitrogen, nitrogen-dimethylaminomethyl propyl acrylate, nitrogen-iso-butyl amino methyl ethyl acrylate, methacrylic acid glycidyl ester, vinyl acetate, propionate, vinyl butyrate, methoxy ethylene, ethyl vinyl ether, allyl glycidyl ethers, methylallyl glycidyl ethers, vinyl cyanide, methacrylonitrile, α-chloro-acrylonitrile, the sub-ethene of cyaniding, acrylamide, Methacrylamide, α-chloropropene acid amides, nitrogen-hydroxyethyl acrylamide, nitrogen-hydroxyethyl methacrylamide, 1,3-butadiene, isopentene, chlorination butadiene, or these a combination.
11. photosensitive resin compositions according to claim 9, it is characterized in that, taking this mixture total weight as 100 weight portions, the content of this first unsaturated monomer is between 20 weight portion～60 weight portions, the content of this second unsaturated monomer is between 0.5 weight portion～20 weight portion, the content of the 3rd unsaturated monomer is between 20 weight portion～50 weight portions, and the content of the 4th unsaturated monomer is between 0 weight portion～15 weight portion.
12. photosensitive resin compositions according to claim 1, is characterized in that, taking this alkali soluble resin gross weight as 100 weight portions, the content of this first alkali soluble resin is between 30 weight portion～90 weight portions.
13. photosensitive resin compositions according to claim 1, is characterized in that, taking this alkali soluble resin gross weight as 100 weight portions, the content of this second alkali soluble resin is between 10 weight portion～70 weight portions.
14. photosensitive resin compositions according to claim 1, it is characterized in that, taking this alkali soluble resin gross weight as 100 weight portions, should be containing the content of the compound of ethene unsaturated group between 10 weight portion～500 weight portions, the content of this light trigger is between 2 weight portion～200 weight portions, the content of this organic solvent is between 500 weight portion～5000 weight portions, and the content of this pigment is between 100 weight portion～800 weight portions.
15. photosensitive resin compositions according to claim 1, is characterized in that, this first compound has suc as formula structure shown in (2),
In formula, R 9and R 10represent respectively hydrogen or methyl, the integer that m is 1～2, a+b=2～6, the integer that a is 1～6, the integer that b is 0～5.
16. 1 kinds of colored filters, comprise by the pixel dyed layer according to arbitrary described photosensitive resin composition forms after photoetching treatment in claim 1 to 15.
17. 1 kinds of liquid crystal indicators, comprise colored filter according to claim 16.
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