CN102627770B - Organosiloxane polymer, preparation method of organosiloxane polymer, color photoresist for color filter, color filter and preparation method of color filter - Google Patents
Organosiloxane polymer, preparation method of organosiloxane polymer, color photoresist for color filter, color filter and preparation method of color filter Download PDFInfo
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- CN102627770B CN102627770B CN201210070934.3A CN201210070934A CN102627770B CN 102627770 B CN102627770 B CN 102627770B CN 201210070934 A CN201210070934 A CN 201210070934A CN 102627770 B CN102627770 B CN 102627770B
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- acid
- general formula
- color
- organosiloxane polymer
- alkyl
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 27
- 229920000642 polymer Polymers 0.000 title claims abstract description 26
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000000758 substrate Substances 0.000 claims abstract description 33
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- -1 phenyl Chemical group 0.000 claims description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000011521 glass Substances 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 229920000728 polyester Polymers 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 15
- 239000000049 pigment Substances 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 10
- 235000019439 ethyl acetate Nutrition 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003377 acid catalyst Substances 0.000 claims description 8
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 238000011161 development Methods 0.000 claims description 6
- 229920000578 graft copolymer Polymers 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 4
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- OOPSAZSKOMIGFX-UHFFFAOYSA-N boric acid;toluene Chemical compound OB(O)O.CC1=CC=CC=C1 OOPSAZSKOMIGFX-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 4
- 238000007337 electrophilic addition reaction Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 229940017144 n-butyl lactate Drugs 0.000 claims description 4
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 2
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007171 acid catalysis Methods 0.000 claims description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005001 aminoaryl group Chemical group 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 claims description 2
- XLGLMVCAOMQNJT-UHFFFAOYSA-N boric acid;chlorobenzene Chemical compound OB(O)O.ClC1=CC=CC=C1 XLGLMVCAOMQNJT-UHFFFAOYSA-N 0.000 claims description 2
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims description 2
- RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 claims description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229950000244 sulfanilic acid Drugs 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 abstract description 10
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 16
- 238000009835 boiling Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003550 marker Substances 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
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- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
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- PRPAGESBURMWTI-UHFFFAOYSA-N [C].[F] Chemical group [C].[F] PRPAGESBURMWTI-UHFFFAOYSA-N 0.000 description 2
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
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- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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Images
Landscapes
- Optical Filters (AREA)
Abstract
The invention relates to an organosiloxane polymer, a preparation method of the organosiloxane polymer, a color photoresist containing the organosiloxane polymer, a color filter adopting the color photoresist and a preparation method of the color filter. The organosiloxane polymer can replace a levelling agent and a coupling agent in a color photoresist formula, and is superior to the traditional levelling agent or the coupling agent in the respect of a degree of polarity matching with other resins and solvents. An intramolecular pressure difference delta-F formed between double interfaces of a coated color film of the color photoresist and a substrate is controllable. The color photoresist realizes control of colloid shrinkage and forms a uniform coating having small shrinkage. The color photoresist realizes flatting of a coated color film, and good adhesiveness of pixel units and align markers on the color filter. A sample obtained by the preparation method of the color filter realizes excellent color uniformity, has high precision and prevents uneven compression of a liquid crystal display panel.
Description
Technical field
The colored Photoresist that the present invention is specifically related to a kind of organo-siloxane high molecular polymer and preparation method thereof and contains this polymkeric substance, and the preparation method of the colored filter of making of colored Photoresist and this colored filter.
Background technology
Colored filter can create by following process: by scattered redness (R) pigment, green (G) pigment and the agent of blueness (B) pigment photoresistor are coated on and on the glass substrate with black matrix, form color film; Vacuum and front baking; Ultraviolet photoetching under mask plate; Develop and make figure and rear baking post bake.The film uniformity of final gained print should be controlled at 3%(and adopt 9 method tests) in; If homogeneity surpasses certain numerical value, on liquid crystal panel, can produce not bright spot or overall color homogeneity in the future inconsistent, as: Japanese Patent, Unexamined Patent 2003-337424 records.Require print edge can not have the retraction of photoresist residual simultaneously, residual if edge has, when panel paster is made, can squeeze broken substrate because pressurized is irregular.The solution of the problems referred to above can realize by adjusting manufacture craft on the one hand; Can realize by adjusting photoresist formula on the other hand.Normally technique and material all will have mutual cooperation.
In recent years, although flat, be coated with (Slit) mode in large-sized glass substrate make colored filter and become mainstream technology, the poor shortcoming of coating is also accompanied by all the time, especially when the color film of the above thickness of coating 2um.Thereby Japanese Patent JP155265/2006 discloses the method that obtains smooth uniform color film in order to improve the problems referred to above, and in Chinese patent CN101081942A, CN1991584A, discloses the mobility of strengthening photoresist with fluorine carbon functional group flow agent.
But the use of flow agent is to select according to integral material, as: solvent, the actual solubility parameter area of resin and special auxiliary agent, mates thereby reach with colloidal dispersion.Though fluorine carbon flow agent has extremely strong reduction surface tension and increases colloid mobility effect; But for viscosity number at 5mpa*s with interior photoresist, do not need to reduce simply the mobility that surface tension increases color film; But need to consider color film and air, pressure reduction in the molecule internal pressure differences Δ F(between the double-deck interface that color film and substrate form is called for short), interfacial tension is poor.While only having Δ F to be less than certain value, could control colloid retraction, the color film being coated on glass substrate can form evenly and the little coating that bounces back.
In addition, colorama resist is when making color film, except avoiding smooth not formed edge retraction; Be also noted that color film another interface problem to glass substrate---stick adherence problem.Even if there is the poor color film of good interfacial tension, the situation that sometimes also there will be pixel lines (Pixel) to come off after exposure imaging; That pixel (Pixel) lines can adherence more sometimes, but trickleer figure, as: contraposition paster mark (Marker) easily comes off.Making to make liquid crystal panel goes wrong.
In order to address this is that, the different siloxanes coupling agent high from silicon (Si) avidity in base plate glass in US Patent No. 4934791 and US5863678.But, if coupling agent mates not with system polarity or usage quantity is improper, often can make again color film flatness decline.
Summary of the invention
The present invention proposes in view of the above problems.The object of the invention is to by a kind of organo-siloxane high molecular polymer is provided, make it in colorama resist, substitute traditional flow agent and coupling agent simultaneously and afterwards can also produce levelling and coupling performance, and the interfacial tension that can effectively control colored filter volume is poor, thereby realize color film planarization.
Another object of the present invention is to provide a kind of preparation method of described organo-siloxane high molecular polymer.
The colored Photoresist that provides a kind of colored filter of applying described organo-siloxane high molecular polymer to use is provided.
Another object of the present invention is to be provided in the colored filter that the described colored Photoresist of a kind of use is made.
A further object of the present invention is to provide the making method of above-mentioned colored filter.
For achieving the above object, the technical solution adopted in the present invention is as follows:
An organosiloxane polymer, has the high molecular polymer of the structural unit that following general formula (1) represents:
General formula (1)
In described general formula (1), X represents Ar base, and Y represents Ar base; R
1represent straight chain or graft copolymer; R
2represent alkylene, containing N alkyl, a kind of containing in O alkyl or halogen atom alkyl; R
3represent hydrogen or methyl; R
4represent methyl or ethyl; N value is 5～300.
In preferred scheme, the structure that X of the present invention represents is selected from C
6～C
30ar base, Y represents C
6～C
30ar base, wherein X and Y can be same base group, can be also different groups.The C more preferred, described X represents
6～C
18phenyl, a kind of in alkyl phenyl or alkoxyl phenyl, Y represents C
6～C
18phenyl, a kind of in alkyl phenyl or alkoxyl phenyl.Wherein X or Y can specifically represent a kind of in the aryl such as phenyl, aminomethyl phenyl, 3,5-dimethylphenyl, trimethylphenyl, ethylphenyl, isopropyl phenyl, butyl phenyl, hydroxy phenyl, p-methoxy-phenyl, acetoxyl group phenyl, butoxy phenyl, chlorophenyl, bromo phenyl, dichloro-phenyl, chloromethyl phenyl, but X of the present invention, Y do not limit above-mentioned group.General formula (5) and general formula (6) are preferably from the compound of following structure:
As preferably, R of the present invention
1represent C
2～C
30saturated straight chain or graft copolymer.Wherein more preferred, described R
1represent C
2～C
16alkyl, polyester based, a kind of in alkyl, polyether base or polyester polyether-based.R
1the compound of base, when selecting, first will consider that the integral polarity of polymkeric substance and lower viscosity require (3-6mpa*s) scope; Secondly, consider color film and air, the molecule internal pressure differences Δ F between the double-deck interface that color film and substrate form is as far as possible little; Realizing Photoresist has good wettability to glass substrate, the mobility having represented, and the homogeneity of color film is lower than 3%; Preferably, R
1can specifically be selected from that polyester based, alkyl are poly-silica-based, a kind of in poly-silica-based, the polyester polyether-based of polyether-modified poly-silica-based, the polyester modification of polyether-based, alkyl, polyether base, poly-silica-based, the many hydroxyls of many hydroxyls modification, acrylate polyester based, fluorine polyester based, perfluoroalkyl polyether base, hydroxyl telechelic polyester base, end hydroxy polyether base, epoxy group(ing) modified poly ester base, epoxy group(ing) modified polyether base, both-end base epoxy group(ing) modified polyether base, both-end base epoxy group(ing) modified poly ester base etc.; Preferred R
1be selected from Mn(number-average molecular weight) a kind of for the polyester based of 1000-50000 scope, alkyl are poly-silica-based, in poly-silica-based, the acrylate polyester based of polyester modification, fluorine polyester based, epoxy group(ing) modified poly ester base, both-end base epoxy group(ing) modified poly ester based prepolymers etc.But R of the present invention
1be not limited to above-mentioned group.
As preferably, R of the present invention
2represent C
2～C
16vinyl, aminoalkyl group, aminoaryl, acryl or epoxy the third oxyalkyl in a kind of.R
2specifically can be preferably from vinyl, N-(2-amino-ethyl), acryl, methacryloyl, acryl propyl group, methacryloyl propyl group, 3-aminopropyl, 3-glycidoxy, 3-glycidoxy propyl group, 3-glycidoxy ethyl, 3-glycidoxy methyl, 3-chloropropyl methyl, 3-chloropropyl ethyl, 3-bromopropyl methyl, 3-bromopropyl ethyl, 2-(3,4-epoxy group(ing) cyclohexyl) methyl, 2-(3,4-epoxy group(ing) cyclohexyl) ethyl, 2-(3,4-epoxy group(ing) cyclohexyl) propyl group; More preferably vinyl, N-(2-amino-ethyl), acryl propyl group, 2-(3,4-epoxy group(ing) cyclohexyl) a kind of in ethyl; But R of the present invention
2be not limited to above-mentioned group.The concrete structure of general formula (3) is listed, but the present invention is not limited to this:
In the present invention, R
3be preferably methyl, R
4be preferably ethyl.
A preparation method for organosiloxane polymer, it comprises the following steps:
(a) synthetic intermediate: by the monomer of following general formula (2) and the monomer of general formula (3) under the effect of acid catalyst in water and solvent, under nitrogen atmosphere, by polycondensation, synthesize the multipolymer intermediate with following general formula (4):
R
1si (OR
3)
3general formula (2)
R
2 msi (OR
4)
4-mgeneral formula (3)
M represents to be less than 4 natural number, and n value is 5～300; Wherein the consumption of catalyzer is the 0.005-3% of monomer (2) and monomer (3) gross weight, and the consumption of general formula (2) is 20-80 weight part; The consumption of general formula (3) is 80-20 weight part, and the consumption of water is 10-300 weight part, and the consumption of solvent is 100-700 weight part;
(b) intermediate is processed: after above-mentioned reaction finishes, by product is gone out in underpressure distillation, then adds normal hexane to separate out intermediate, obtain having general formula after the suction filtration intermediate of (4);
(c) synthetic product: by structural formula be following general formula (5) monomer and general formula (6) monomer and general formula (4) intermediate in solvent, under nitrogen atmosphere, by the preparation of acid catalysis electrophilic addition reaction, there is the product of general formula (1):
CH
2=CHOCH
2x general formula (5)
CH
2=CHOCH
2y general formula (6)
Intermediate in reaction (4) is 10:1-500:1 with the mass ratio of monomer (5) or monomer (6), and the consumption of catalyzer accounts for 0.01-0.5 weight part in addition reaction substrate, and solvent load is 5-20 times of addition substrate weight; In above-mentioned general formula, the X that wherein occurred represents Ar base, and Y represents Ar base; R
1represent straight chain or graft copolymer; R
2represent alkylene, containing N alkyl, a kind of containing in O alkyl or halogen atom alkyl; R
3represent hydrogen or methyl; R
4represent methyl or ethyl; N value is 5～300.
In preferred scheme, in (a) of the present invention step, acid catalyst is hydrochloric acid, sulfuric acid, nitric acid, tosic acid hydrate, a kind of in toluene boric acid, ethyl sulfate, organic sulfonic acid alkyl ester, but is not limited to above-mentioned acid; This reaction process can be by controlling by changing acid catalyst kind, consumption and interpolation pattern, consumption at above-mentioned reacting middle catalyst is that 100-700 weight part is comparatively suitable scope, and the interpolation pattern of acid catalyst is to add control by constant pressure funnel.
Described solvent is a kind of in acetone, tetrahydrofuran (THF), benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ethyl acetate, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, dipropylene glycol methyl ether.Wherein the consumption of catalyzer is the 0.005-3% of monomer (2) and monomer (3) gross weight, is that speed of reaction is too low because if be less than 0.005%, and hydrolysis is difficult to completely, will have influence on the carrying out of the electrophilic addition reaction of lower one-step polycondensation reaction and lower step; If be greater than 3%, speed of reaction is too high, and the polycondensation of lower step can not be carried out.
In described (c) step, acid catalyst is formic acid, acetic acid, phenylformic acid, Whitfield's ointment, tartrate, oxalic acid, succinic acid, thiazole-4 carboxylic acid, pyridine-3 carboxylic acid, pyridine-4 carboxylic acid, oxygen carboxylic acid fluoride, oxyacetic acid, thiocarboxylic acid, Cyclopentane carboxylic acid, cyclopropane dicarboxylic acid, contains carboxylic acid fluoride, pyridazine carboxylic acid, imidazolyl carboxylic acid; Propyl sulfonic acid, butyl sulfonic acid, sulfanilic acid, α-naphthalenesulfonicacid, beta-naphthalenesulfonic-acid, 2-aminoethyl sulfonic acid, Phenylsulfonic acid, tosic acid, 4-chlorobenzene boric acid, a kind of in toluene boric acid, silicic acid, sulfuric acid, hydrochloric acid, Hydrogen bromide, phosphoric acid, phosphorous acid, nitric acid; The consumption of catalyzer is between 0.01-0.5 part of addition reaction substrate mass parts.Because if be less than 0.01 part, the carbonium ion intermediate product in the middle of reaction is not enough, and addition reaction is difficult to completely; If be greater than 0.5 part, can hinder monomer (5), the represented compound of monomer (6) reacts with intermediate (4).
Described solvent is a kind of in acetone, tetrahydrofuran (THF), benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ethyl acetate, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, dipropylene glycol methyl ether.
In preferred scheme, in described (c) step, the dimension of addition reaction between 120-200 ℃, 150-180 ℃ preferably.If during lower than 120 ℃, electrophilic addition reaction carries out not exclusively; If during higher than 200 ℃, probably surpass monomer (4) or/and the boiling point of the compound of the structural unit that monomer (5) represents causes substrate volatilization, reduced the transformation efficiency of polycondensation.More preferred, temperature of reaction is 150-180 ℃, and best temperature of reaction is 180 ℃.
A colored filter colorama resist, it is the following component comprising in weight part:
In above-mentioned colorama resist, described pigment dispersion color paste is in pigment, to add dispersion agent or/and dispersion aids solubilizing agent mixes, and the preferred blending ratio (mass ratio) of three is 1:0.05-0.4:80-85; Wherein pigment is pigment dyestuff, is preferably red PR177, PR254, yellow PY139, PY150, green PG36, PG58, blue PB156, purple PV23, PV37 pigment; Colorama resist of the present invention, according to the difference of the color of the pigment dyestuff of selecting, can form red pixel, green pixel and the blue pixel etc. of colour filter aptly.And in the time of within the scope of this, dispersion system of pigment is stable and have good pixel light resolving power; Dispersion agent in mill base or dispersion aids, can improve the stability of coloured composition, obtain suitable liquid viscosity and surface tension, in the present invention, as pigment dispersing agent, preferably can use the carboxylicesters of hydroxyl, a kind of in the poly-urethane of the salt of high molecular poly carboxylic acid, long-chain, modified polyurethane, modified polyacrylate, polyether ester type anionic promoting agent, polyxyethylated phosphoric acid ester, pigment derivative etc.Wherein solvent is one or more mixing in methylethylketone, ethyl cellosolve, glycol dimethyl ether, ethylene glycol diethyl ether, Propylene Glycol Dimethyl Ether, diethylene glycol dimethyl ether, 2-oxyethyl group propyl alcohol, 2-methoxypropanol, 3-methoxybutanol, pimelinketone, cyclopentanone, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, butylacetate etc., but the present invention is not limited only to this.
In above-mentioned colored Photoresist, the selection of described binder will consider that it has caustic solubility, therefore require in its structure, to there is caustic solubility group, as preferably, binder methacrylic acid of the present invention and butyl methacrylate copolymer, methacrylic acid and cyclohexyl methacrylate multipolymer, methacrylic acid and cyclohexyl methacrylate and styrol copolymer, methacrylic acid and cyclohexyl methacrylate and methacrylic acid-2 – hydroxy methacrylate multipolymer, a kind of in methacrylic acid and cyclohexyl methacrylate and vinylbenzene and methacrylic acid-2 – hydroxy methacrylate multipolymer, the acid number of binder is 70KOH/g-150KOH/g, acid number surpasses in the situation of 150KOH/g, and acrylic resin is excessive to the solvability of alkali, and development proper range (development width) narrows down, on the other hand, if be less than 70KOH/g, the poorly soluble development time that causes of alkali is elongated, this is disadvantageous in technique.
In above-mentioned colored Photoresist, described phtotpolymerizable monomer is one or more mixing in pentaerythritol triacrylate, Dipentaerythritol diacrylate, Dipentaerythritol triacrylate, Dipentaerythritol five acrylate, dipentaerythritol acrylate etc.The consumption of monomer is selected very important, may cause the pixel edge prepared by colorama resist irregular when phtotpolymerizable monomer consumption is less than 0.1 weight part in each component; And when monomer content is during higher than 30 weight part, this colorama resist difficulty of developing in developing solution even can not be developed.
In above-mentioned colored Photoresist, described initiator is selected from 2, 4-trichloromethyl (4 '-p-methoxy-phenyl)-6-triazine, 2, 4-trichloromethyl-(4 '-methoxyl-styrene)-6-triazine, 2, 2 '-bis-(2-chloro-phenyl-s) 4, 4', 5, 5 '-tetraphenyl bisglyoxaline, second phthalein benzene compound (Irg-369), 2 – hydroxy-2-methyl-1-phenyl-propane-l-ketone, 2-methyl-(4-methylbenzene sulfenyl)-2-beautiful jade-l-propane-1-ketone (Irg-907) and 2-phenmethyl-2-dimethylamino-1-(4-beautiful jade phenyl) a kind of in-butane-l-ketone etc., but be not limited to above-mentioned several.In order to guarantee that photoresist can carry out good polymerizing curable, and reach stronger tack, within the consumption of initiator must be controlled at suitable scope, when initiator amount is less than 0.1 weight part in each component, in light reaction procedure, the photopolymerization reaction of monomer is insufficient, the initiator that has neither part nor lot in reaction when initiator amount during higher than 3 weight part is stayed in photoresist, make the loss of transmission of system, so in the present invention, the consumption of initiator is between 0.1-3 weight part.
In above-mentioned colored Photoresist, described auxiliary agent can further be selected from one or more in photosensitizers tinting material curing catalyst, heat polymerization inhibitor, softening agent, sensitizing agent, defoamer, adhesion promotor, filler etc.Auxiliary agent consumption in colorama resist, be 0.1-1 weight part; When auxiliary dosage surpasses 1 weight part, when coating is dry, easily generation surface irregularity, smoothness easily worsen.
In above-mentioned colored Photoresist, described solvent is selected from one or more in methylethylketone, ethyl cellosolve, glycol dimethyl ether, ethylene glycol diethyl ether, Propylene Glycol Dimethyl Ether, diethylene glycol dimethyl ether, 2-oxyethyl group propyl alcohol, 2-methoxypropanol, 3-methoxybutanol, pimelinketone, cyclopentanone, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, butylacetate etc., but the present invention is not only for above-mentioned several.
A colored filter, it comprises on glass substrate with black matrix, glass substrate and is coated with three layers of colorama resist pattern of pixels as claimed in claim 10, three layers of colorama resist pattern of pixels are followed successively by three kinds of colors of red, green, blue.
A manufacture method for colored filter, it comprises the following steps:
A) processing substrate: form black matrix on glass substrate;
B) make colour filter: on above-mentioned glass substrate, be coated with red Photoresist as claimed in claim 10 and cover black matrix and form the color film of the first layer, more successively through mask shelter, partial exposure, development, cure step form the first layer pixel; Repeat again above-mentioned steps and form respectively green and the blue second layer and the 3rd layer of pixel, be finally made into colored filter.
Specifically according to following step, make, first glass substrate is cleaned, the carbon family organic materials that is then 3.5-5 by optical density(OD) deposits on glass substrate, after this, utilizes photolithography to scheme black matrix for glass substrate formation; Black matrix can arrange like this: the edge section of unit picture element and will corresponding to each other for the region of TFT is set, to can be blocked in the light that the light source in the unsettled region of electric field sends; On the whole surface of glass substrate, coating thickness scope is about the colorama resist of the present invention of 1-3 μ m afterwards, utilizes spin-coating method or the red color film of flat painting method coating the first layer to glass substrate, thoroughly to cover black matrix; Except the specific region of the color film of the first layer, (be and form figure and remaining region), with the opaque section of mask, shelter the whole surface of the color film of the first layer, by UV rayed, (generally speaking the color film of the first layer is carried out to partial exposure, the colorama resistance layer of colour filter has the negative characteristic of the unexposed portion that can remove colorama resist, so just expose by the transparent part of mask in the specific region that is used to form colorama resist figure); Afterwards, the red color film of the first layer that has changed photochemistry structure by exposure is dipped in developing solution, adopts infusion method or spraying process to develop, remove its unexposed portion, then at the temperature of 230 ℃, allow the red color film of the first layer harden; Then on the whole surface on the glass substrate that comprises the first layer red pixel layer, be coated with second layer green tint film, according to the step with the first layer pixel, carry out partial exposure, development, sclerosis, formation second layer pixel layer; Then on the whole surface of glass substrate that comprises first and second layers of pixel, be coated with the 3rd layer of blue color film it is carried out to partial exposure, develop, sclerosis, finally forms colored filter.
Compared to existing technology, beneficial effect of the present invention is:
1. organo-siloxane high molecular polymer of the present invention, join in the middle of colorama resist (Color Resist) formula, can substitute flow agent and coupling agent simultaneously, formula is simplified, in the polarity with other resins and solvent more compatible aspect matching degree;
2. the colorama resist that the present invention makes, the molecule internal pressure differences Δ F between the double-deck interface that the color film of coating and substrate form is controlled, thereby realize, colloid retraction is controlled, and forms evenly and the little coating that bounces back;
3. the colorama resist that the present invention makes, when making the color film of coating realize planarization, the pixel lines on colored filter and alignment mark all can be good sticks adherence;
4. it is even that the liquid crystal display device colored filter that the present invention and manufacture method thereof are made can be realized color; Make liquid crystal panel without pressure uneven phenomenon; The performances such as the good and high precision of pixel adherence.
Below in conjunction with the drawings and specific embodiments, the present invention is described in further detail.
Accompanying drawing explanation
Fig. 1 represents in comparative example table 1, from the edge thickness data acquisition of the monochromatic sheet of contrast experiment (1)-(7) in a system of coordinates, wherein, edge thickness be 3 times of thickness with interior data results, the posterior border noresidue of developing when making band pixel line bar print;
Fig. 2 represents that comparative example (2) is when making band pixel line bar print, the electromicroscopic photograph that has pixel to come off;
Fig. 3 represents that comparative example (5) is when making band pixel line bar print, the electromicroscopic photograph that has marker to come off;
Fig. 4 represents that comparative example (7) is when making band pixel line bar print, the electromicroscopic photograph that pixel and marker all do not come off.
Embodiment
Below the preferred specific embodiment of the present invention and comparative example.
Embodiment [1]
Get the polyether-modified polydimethylsiloxane of BYK-302() 1.62 parts, 6.49 parts of the compounds shown in chemical formula 3-2; 20 parts of pimelinketone; Add in four-hole boiling flask, and put into magneton in four-hole boiling flask, device prolong, thermometer; Be communicated with nitrogen, after packing constant pressure funnel into, 3 parts of sulfuric acid (60% concentration) are arranged on four-hole boiling flask, in 80rpm stirring velocity access 70 degree water-baths, react 2 hours, underpressure distillation is cooled to 50 degree except by product in 0.5 hour, continue reaction 8 hours, finish reaction, add 60 parts of normal hexanes, product is separated out, cloth formula funnel suction filtration, the dry intermediate 4-1 that obtains.
Embodiment [2]
Get the two key end capped polyether modified organic silicons of Ciba-EFKA-3883() 3.24 parts, and 3.61 parts of the compounds that represent of 1.26 parts of compounds representing of above-mentioned chemical formula 3-1 and 5-6; 20 parts of pimelinketone; Add in four-hole boiling flask, and put into magneton in four-hole boiling flask, device prolong, thermometer, is communicated with nitrogen; 3 parts of moisture nitric acid (1000ppm) are arranged on four-hole boiling flask after packing constant pressure funnel into, in 240rpm stirring velocity access 60 degree water-baths, react 2 hours, underpressure distillation removes by product for 0.5 hour, be cooled to 50 degree, continue reaction 8 hours, finish reaction, add 60 parts of normal hexanes, product is separated out, cloth formula funnel suction filtration, the dry intermediate 4-2 that obtains.
Embodiment [3]
Get the two key end capped polyether modified organic silicons of Ciba-EFKA-3883() and the fluorine-containing carbon organic silicon modified by polyether of Ciba-EFKA-3034() respectively 1.62 parts, and 4.87 parts of the compounds that represent of above-mentioned chemical formula 3-2; 20 parts of pimelinketone; Add in four-hole boiling flask, and put into magneton in four-hole boiling flask, device prolong, thermometer, is communicated with nitrogen, after 3 parts of sulfuric acid (60% concentration) pack constant pressure funnel into, is arranged on four-hole boiling flask, in 120rpm stirring velocity access 60 degree water-baths, react 2 hours, underpressure distillation is cooled to 50 degree except by product in 0.5 hour, continue reaction 8 hours, finish reaction, add 60 parts of normal hexanes, product is separated out, cloth formula funnel suction filtration, the dry intermediate 4-3 that obtains.
Embodiment [4]
Product intermediate 4-1, and 0.62 part of the compound that represents of above-mentioned chemical formula 5-2; PMA30 part; 0.03 part of oxalic acid; Add in four-hole boiling flask, put into magneton, device prolong, constant pressure funnel, thermometer; Be communicated with nitrogen, in 120rpm stirring velocity access 120 degree oil baths, react 6 hours, finish reaction, obtain the compound 1-1 that general formula (1) represents.
Embodiment [5]
Product intermediate 4-2, and 0.20 part of the compound that represents of 0.42 part of the compound that represents of above-mentioned chemical formula 5-6 and chemical formula 5-2; PMA30 part; 0.01 part of beta-naphthalenesulfonic-acid; Add in four-hole boiling flask, put into magneton, device prolong, constant pressure funnel, thermometer; Be communicated with nitrogen, in 120rpm stirring velocity access 170 degree oil baths, react 6 hours, finish reaction, obtain the compound 1-2 that general formula (1) represents.
Embodiment [6]
Product intermediate 4-3, and 0.42 part of the compound that represents of above-mentioned chemical formula 5-2; PMA30 part; 0.01 part of beta-naphthalenesulfonic-acid; Add in four-hole boiling flask, put into magneton, device prolong, constant pressure funnel, thermometer; Be communicated with nitrogen, in 120rpm stirring velocity access 150 degree oil baths, react 6 hours, finish reaction, obtain the compound 1-3 that general formula (1) represents.
Embodiment [7]
(comparative example)
Below, take green light resist as example, on glass substrate, be coated with monochromatic color film, now, can form two interfaces: one is the air-resist interface of the upper surface formation of air and color film, another is the lower surface of color film and the resist-glass interface that glass substrate forms; Color membrane molecule on interface is different with the molecular attraction being subject in dispersed system interior molecules, has produced surface tension F
air-resistand surface tension (being wetting tension) F
resist-glass; The internal pressure of condensed matter is the 10^5 order of magnitude of the internal pressure of gaseous substance, so F
air-resistjust equal the internal pressure of the color membrane molecule of upper epidermis, it is inner that direction is pointed to color film; Making a concerted effort for F of the internal pressure of the color membrane molecule in the internal pressure of glass and lower top layer
glass-resist, because solid internal pressure is greater than liquid internal pressure power, so F
glass-resistpoint to inside glass; And the power that the color membrane molecule in lower top layer is subject to is F
glass-resistreactive force, i.e. tension force F
resist-glass, and size and F
glass-resistequate, it is inner that direction is pointed to color film; So, F
air-resistand F
resist-glassbe the tension force of a pair of opposite direction, their making a concerted effort is molecule internal pressure differences Δ F; Common F
air-resist is less than F
resist-glass, the hydromeehanics reason that Here it is photoresist can natural flow.
Take embodiment [7] formula as basis, do not add the compound of general formula (1) and the blank test of flow agent and coupling agent (1) as a comparison case; The compound that does not add general formula (1), forms comparative example (2)--(4) by flow agent or/and coupling agent joins in the formula of embodiment [7] respectively; Do not add flow agent or/and coupling agent, respectively by compound 1-1,1-2,1-3 adds in the middle of the formula of embodiment [7], forms comparative example (5)--(7).The monochrome coloured silk film substrate drying after making respectively afterwards with the monochromatic filter (a) of pixel with after not adding mask exposure directly, so both can detect pixel adhesion property, can measure again the thickness data of retraction and the thickness data at edge, surveying instrument uses SE500-59 type roughness tester, the results are shown in following table 1(thickness unit: μ m)
Table 1
| Simultaneous test | General formula (1) | Flow agent | Coupling agent | Thickness | Edge thickness | Adherence |
| （1） | -- | -- | -- | 1.102 | 6.823 | ● |
| （2） | -- | Fluorine carbon | -- | 1.043 | 4.225 | ● |
| （3） | -- | -- | Siloxanes | 1.072 | 6.457 | ○ |
| （4） | -- | Siloxanes | Siloxanes | 1.170 | 2.849 | △ |
| （5） | 1-1 | -- | -- | 1.085 | 2.551 | △ |
| （6） | 1-2 | -- | -- | 1.007 | 3.122 | ○ |
| （7） | 1-3 | -- | -- | 1.114 | 2.243 | ○ |
Note: ● represent that pixel lines have the △ of coming off to represent that pixel lines do not come off, but Marker there are come off zero expression pixel and Marker all not to come off.
Claims (14)
1. an organosiloxane polymer, is characterized in that, has the high molecular polymer of the structural unit of following general formula (1) expression:
In described general formula (1), X represents Ar base, and Y represents Ar base; R
1represent straight chain or graft copolymer; R
2represent alkylene, containing N alkyl, a kind of containing in O alkyl or halogen atom alkyl; R
3represent hydrogen or methyl; R
4represent methyl or ethyl; N value is 5～300.
2. organosiloxane polymer according to claim 1, is characterized in that, the structure that described X represents is selected from C
6～C
30ar base, Y represents C
6～C
30ar base, X is identical group or different group from Y.
3. organosiloxane polymer according to claim 1, is characterized in that, described X represents C
6～C
18phenyl, alkyl phenyl or alkoxyl phenyl, Y represents C
6～C
18phenyl, alkyl phenyl or alkoxyl phenyl.
4. organosiloxane polymer according to claim 1, is characterized in that, described R
1represent C
2～C
30saturated straight chain or graft copolymer.
5. organosiloxane polymer according to claim 1, is characterized in that, described R
1represent C
2～C
16alkyl, polyester based, alkyl, polyether base or polyester polyether-based.
6. organosiloxane polymer according to claim 1, is characterized in that, described R
2represent C
2～C
16vinyl, aminoalkyl group, aminoaryl or epoxy the third oxyalkyl in a kind of.
7. a preparation method for organosiloxane polymer, is characterized in that, it comprises the following steps:
(
a) synthetic intermediate: by the monomer of following general formula (2) and the monomer of general formula (3) under the effect of acid catalyst in water and solvent, under nitrogen atmosphere, by polycondensation, synthesize the multipolymer intermediate with following general formula (4):
R
1si (O R
3)
3general formula (2)
R
2 msi (O R
4)
4-mgeneral formula (3)
M represents to be less than 4 natural number, and n value is 5～300;
(b) intermediate is processed: after above-mentioned reaction finishes, by product is removed in underpressure distillation, then adds normal hexane to separate out intermediate, obtain having general formula after the suction filtration intermediate of (4);
(c) synthetic product: by structural formula be following general formula (5) monomer and general formula (6) monomer and general formula (4) intermediate in solvent, under nitrogen atmosphere, by the preparation of acid catalysis electrophilic addition reaction, there is the product of general formula (1):
CH
2=CHOCH
2x general formula (5)
CH
2=CHOCH
2y general formula (6)
In above-mentioned general formula, the X that wherein occurred represents Ar base, and Y represents Ar base; R
1represent straight chain or graft copolymer; R
2represent alkylene, containing N alkyl, a kind of containing in O alkyl or halogen atom alkyl; R
3represent hydrogen or methyl; R
4represent methyl or ethyl; N value is 5～300.
8. the preparation method of organosiloxane polymer according to claim 7, it is characterized in that, in described (a) step, acid catalyst is hydrochloric acid, sulfuric acid, nitric acid, tosic acid hydrate, to toluene boric acid, ethyl sulfate, a kind of in organic sulfonic acid alkyl ester, described solvent is acetone, tetrahydrofuran (THF), benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ethyl acetate, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, a kind of in dipropylene glycol methyl ether.
9. the preparation method of organosiloxane polymer according to claim 7, it is characterized in that, in described (c) step, acid catalyst is formic acid, acetic acid, phenylformic acid, Whitfield's ointment, tartrate, oxalic acid, succinic acid, thiazole-4 carboxylic acid, pyridine-3 carboxylic acid, pyridine-4 carboxylic acid, oxyacetic acid, thiocarboxylic acid, Cyclopentane carboxylic acid, cyclopropane dicarboxylic acid, contains carboxylic acid fluoride, pyridazine carboxylic acid, imidazolyl carboxylic acid; Propyl sulfonic acid, butyl sulfonic acid, sulfanilic acid, α-naphthalenesulfonicacid, beta-naphthalenesulfonic-acid, 2-aminoethyl sulfonic acid, Phenylsulfonic acid, tosic acid, 4-chlorobenzene boric acid, a kind of in toluene boric acid, silicic acid, sulfuric acid, hydrochloric acid, Hydrogen bromide, phosphoric acid, phosphorous acid, nitric acid; Solvent is a kind of in acetone, tetrahydrofuran (THF), benzene, toluene, xylol, Anaesthetie Ether, methylene dichloride, chloroform, ethyl acetate, propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, pimelinketone, n-Butyl lactate, dipropylene glycol methyl ether.
10. a colored filter colorama resist, is characterised in that, it is the following component comprising in weight part:
Organo-siloxane high molecular polymer 0.1-30 part of claim 1 formula of (1)
Pigment dispersion color paste 30-50 part
Binder 0.1-30 part
Phtotpolymerizable monomer 0.1-30 part
Light trigger 0.1-3 part
Auxiliary agent 0.1-1 part
Solvent 60-90 part.
11. colored filter according to claim 10 colorama resists, are characterised in that, described pigment dispersion color paste is in pigment, to add dispersion agent or/and dispersion aids solubilizing agent mixes.
12. colored filter according to claim 10 colorama resists, be characterised in that, described binder is a kind of in methacrylic acid and butyl methacrylate copolymer, methacrylic acid and cyclohexyl methacrylate multipolymer, methacrylic acid and cyclohexyl methacrylate and styrol copolymer, methacrylic acid and cyclohexyl methacrylate and methacrylic acid-2 – hydroxy methacrylate multipolymer, methacrylic acid and cyclohexyl methacrylate and vinylbenzene and methacrylic acid-2 – hydroxy methacrylate multipolymer; The acid number of binder is 70KOH/g-150KOH/g.
13. 1 kinds of colored filters, it is characterized in that, it comprises on glass substrate with black matrix, glass substrate and is coated with three layers of colorama resist pattern of pixels as claimed in claim 10, and three layers of colorama resist pattern of pixels are followed successively by three kinds of colors of red, green, blue.
The manufacture method of 14. 1 kinds of colored filters, is characterized in that, it comprises the following steps:
A) processing substrate: form black matrix on glass substrate;
B) make colour filter: the as claimed in claim 10 colored Photoresist that is coated with the first color on above-mentioned glass substrate covers black matrix and forms the color film of the first layer, more successively through mask shelter, partial exposure, development, cure step form the first layer pixel; Repeat again above-mentioned steps and form respectively green and blue second layer pixel and the 3rd layer of pixel, be finally made into colored filter.
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| CN105037627B (en) * | 2015-08-21 | 2017-01-25 | 深圳市联深化学技术有限公司 | Oligomeric resin, preparation method thereof and application thereof in color photoresist |
| JP6640381B2 (en) * | 2016-12-08 | 2020-02-05 | シャープ株式会社 | Composition for black matrix, black matrix, and method for producing black matrix |
| CN120904744B (en) * | 2025-10-10 | 2025-12-16 | 信联电子材料科技股份有限公司 | An anti-reflective coating composition and its preparation method |
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| US6046283A (en) * | 1996-12-31 | 2000-04-04 | Massachusetts Institute Of Technology | Rubber-modified rigid silicone resins and composites produced therefrom |
| CN101021583A (en) * | 2006-02-15 | 2007-08-22 | 虹创科技股份有限公司 | Colour optical filter separating wall and producing method thereof, colour filter and producing method thereof |
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| US6046283A (en) * | 1996-12-31 | 2000-04-04 | Massachusetts Institute Of Technology | Rubber-modified rigid silicone resins and composites produced therefrom |
| CN101021583A (en) * | 2006-02-15 | 2007-08-22 | 虹创科技股份有限公司 | Colour optical filter separating wall and producing method thereof, colour filter and producing method thereof |
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