WO2022142537A1 - 一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 - Google Patents
一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 Download PDFInfo
- Publication number
- WO2022142537A1 WO2022142537A1 PCT/CN2021/120972 CN2021120972W WO2022142537A1 WO 2022142537 A1 WO2022142537 A1 WO 2022142537A1 CN 2021120972 W CN2021120972 W CN 2021120972W WO 2022142537 A1 WO2022142537 A1 WO 2022142537A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- parts
- fluorine
- resin composition
- containing resin
- film
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 28
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 21
- 239000011737 fluorine Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 14
- -1 methacryloyl Chemical group 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 239000011347 resin Substances 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000003085 diluting agent Substances 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 3
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 11
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 238000011161 development Methods 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-UHFFFAOYSA-N 0.000 claims description 4
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 239000007822 coupling agent Substances 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- ZRDYULMDEGRWRC-UHFFFAOYSA-N (4-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O ZRDYULMDEGRWRC-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 229930003836 cresol Natural products 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 3
- ZDROXNKXVHPNBJ-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=C(O)C=CC=C1O ZDROXNKXVHPNBJ-UHFFFAOYSA-N 0.000 claims description 2
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 claims description 2
- IGKOKEBHGRCHSR-UHFFFAOYSA-N bis(3,4,5-trihydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 IGKOKEBHGRCHSR-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- WQHAWOFWMDZBLB-UHFFFAOYSA-N (2,4-dihydroxyphenyl)-phenylmethanone;(2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1.OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 WQHAWOFWMDZBLB-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000003893 lactate salts Chemical class 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 abstract 1
- 230000035699 permeability Effects 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 239000010408 film Substances 0.000 description 97
- 238000011156 evaluation Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 238000002834 transmittance Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 6
- 239000011229 interlayer Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 4
- OSJIQLQSJBXTOH-UHFFFAOYSA-N 8-tricyclo[5.2.1.02,6]decanylmethyl prop-2-enoate Chemical compound C12CCCC2C2CC(COC(=O)C=C)C1C2 OSJIQLQSJBXTOH-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000010292 electrical insulation Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003903 lactic acid esters Chemical class 0.000 description 2
- 150000003017 phosphorus Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- XEDWWPGWIXPVRQ-UHFFFAOYSA-N (2,3,4-trihydroxyphenyl)-(3,4,5-trihydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC(O)=C(O)C(O)=C1 XEDWWPGWIXPVRQ-UHFFFAOYSA-N 0.000 description 1
- PJMXUSNWBKGQEZ-UHFFFAOYSA-N (4-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(O)C=C1 PJMXUSNWBKGQEZ-UHFFFAOYSA-N 0.000 description 1
- LAIJAUHBAWLPCO-UHFFFAOYSA-N (4-tert-butylcyclohexyl) prop-2-enoate Chemical compound CC(C)(C)C1CCC(OC(=O)C=C)CC1 LAIJAUHBAWLPCO-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- BFQFFNWLTHFJOZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=C3OCOC3=CC=2)=N1 BFQFFNWLTHFJOZ-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- MXVZVCCKUVRGQC-UHFFFAOYSA-N 3-hexylpyrrole-2,5-dione Chemical compound CCCCCCC1=CC(=O)NC1=O MXVZVCCKUVRGQC-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- YOVILDMQHOAOBN-UHFFFAOYSA-N CC(C)(C)OC(C=C1)=CC=C1C1=CC=CC=C1CC(C(O)=O)=C Chemical compound CC(C)(C)OC(C=C1)=CC=C1C1=CC=CC=C1CC(C(O)=O)=C YOVILDMQHOAOBN-UHFFFAOYSA-N 0.000 description 1
- NFMYADHDLPBXQU-UHFFFAOYSA-N CC1OCC1.C(C=C)(=O)O Chemical compound CC1OCC1.C(C=C)(=O)O NFMYADHDLPBXQU-UHFFFAOYSA-N 0.000 description 1
- AXBIQLMLCIIPLD-UHFFFAOYSA-N Cl.Cl.Cl.NCCN(CCN)CC1=CC=CC=C1[N+]([O-])=O Chemical group Cl.Cl.Cl.NCCN(CCN)CC1=CC=CC=C1[N+]([O-])=O AXBIQLMLCIIPLD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3r)-3-hydroxybutyl] (3r)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 description 1
- XLXOGJYARRBRPZ-UHFFFAOYSA-N [2,3-di(prop-2-enoyloxy)-3-propoxypropyl] prop-2-enoate Chemical compound CCCOC(OC(=O)C=C)C(OC(=O)C=C)COC(=O)C=C XLXOGJYARRBRPZ-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- YXKZOOQDQQINBJ-UHFFFAOYSA-N naphthalene-1,4-dione;azide Chemical group [N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 YXKZOOQDQQINBJ-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- IYVPXMGWHZBPIR-UHFFFAOYSA-N propyl 3-ethoxypropanoate Chemical compound CCCOC(=O)CCOCC IYVPXMGWHZBPIR-UHFFFAOYSA-N 0.000 description 1
- JCMFJIHDWDKYIL-UHFFFAOYSA-N propyl 3-methoxypropanoate Chemical compound CCCOC(=O)CCOC JCMFJIHDWDKYIL-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 238000011077 uniformity evaluation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
Definitions
- the present invention relates to the technical field of resin synthesis, and more particularly to a fluorine-containing resin composition, a preparation method and a preparation method of a cured film comprising the same.
- Color filters and thin film transistors are the key components for liquid crystal displays to achieve color display, and their surface flatness and light transmittance directly affect the performance of the display.
- a layer of cured film protective layer of resin material can be spin-coated on the surface of the filter film, namely: OC film (Over Coat), to improve the color
- OC film Over Coat
- the flatness and light transmittance of the filter film surface are also required to have good heat resistance and strength to protect the filter film from damage and improve service life.
- a cured film is usually used as an interlayer insulating film to cover the TFT element, and the interlayer insulating film is mainly used for interlayer insulation, protection and planarization of each film.
- the resin composition for forming the cured film is required to have good coating performance, higher electrical insulation and light transmission. properties, while having better chemical resistance, heat resistance, hardness and better adhesion to meet the needs.
- the present invention provides a fluorine-containing resin combination with good coating performance, electrical insulation and light transmittance, as well as better chemical resistance, heat resistance, hardness and better adhesion material and preparation method.
- a fluorine-containing resin composition comprising the following raw materials in parts by weight: 18-42 parts of alkali-soluble resin (A) containing compound (I), 2- 8 parts, 0.3-1.2 parts of sensitizer, 0-15 parts of active diluent, 60-90 parts of solvent, 1-8 parts of auxiliary;
- R 1 , R 1 ', R 2 , R 2 ' are each independently selected from: hydrogen, hydroxy, C1-C4 alkyl or C1-C4 alkoxy;
- Ring B is selected from phenyl, naphthyl or anthracenyl.
- the structural formula of the compound (I) monomer is any one of the following structural formulas:
- the preparation method of the alkali-soluble resin (A) is as follows: adding 2-5 parts of compound (I) monomers, 1-5 parts of acrylic monomers, 10-30 parts of acrylate monomers, 2-5 parts of limide monomer, 1-5 parts of initiator, 0.2-1.0 part of molecular weight regulator and 50-84 parts of organic solvent are mixed and heated to 75-80 °C, kept for 3-6 hours, cooled to The reaction is terminated at room temperature to obtain the alkali-soluble resin (A); wherein, the usage amount of the compound (I) is added at 8% to 15% according to the solid content of the alkali-soluble resin (A);
- the acrylic monomer is methacrylic acid; the acrylic ester monomer is one of methyl methacrylate, lauryl methacrylate, tetrahydrofurfuryl methacrylate and glycidyl methacrylate one or more; the maleimide monomer is N-cyclohexyl maleimide; the initiator is azobisisoheptanenitrile; the molecular weight regulator is ⁇ -methylstyrene polymer.
- the photoinitiator is obtained by condensation reaction of a phenolic compound and 215-naphthoquinone azide sulfonyl chloride according to a molar ratio of 1:0.5-1:4; wherein, the photoinitiator is relative to the hydroxyl group in the phenolic compound.
- 215-Naphthoquinone azide sulfonyl chloride with a material ratio of 50% to 100% by mole is used for condensation.
- the phenolic compound is 4-hydroxybenzophenone, 2,4-dihydroxybenzophenone, 2,4,6-trihydroxybenzophenone, 2,3,4-trihydroxydibenzophenone Benzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, 2,3,4,2',6'-penta Hydroxybenzophenone, 2,3,4,3',4',5'-hexahydroxybenzophenone, 3,4,5,3',4',5'-hexahydroxybenzophenone, Bisphenol A, Spirobisindan, Cresol Trimer, Tris(4-hydroxyphenyl)methane, 1,1,1,-Tris(tetrahydroxyphenyl)ethane, 1,1,1,-Tris (4-hydroxyphenyl)propane, 1,1,1,-tris(4-hydroxyphenyl)butane, 1,1,-bis(4-hydroxyphenyl)cyclohexane and ⁇
- B-1 (4-hydroxybenzophenone), B-2 (4,4'-dihydroxybenzophenone), B-3 (2,4-dihydroxybenzophenone), B-4 (2,3,4-trihydroxybenzophenone), B-5 (2,3,4,4'-tetrahydroxybenzophenone), B-6 (spirobisindan), B-7 ( cresol trimer), B-8 (bisphenol A);
- the photoinitiator is obtained by condensation reaction of one of B-4, B-5 and B-8 with 215-naphthoquinone azide sulfonyl chloride, more preferably B-8 and 215-naphthoquinone azide sulfonyl chloride
- the acid chloride is obtained by condensation reaction according to the molar ratio (1:0.5)-(1:4).
- the photoinitiator is any one or more of phosphorus salts, iodonium salts, o-nitrobenzyl salts, oxime ketone esters and triazine compounds.
- the phosphorus salt is phenylthiophenyldiphenylsulfonium hexafluorophosphate and/or bis(4,4'-thioethertriphenylsulfonium) hexafluorophosphate;
- the iodonium salt is any one or more of bisthiophene ring iodonium salt, fluorenone phenyl iodonium salt and polystyrene iodogermanium-hexafluoroantimonate;
- the o-nitrobenzyl salt is N,N-bis(2-aminoethyl)-N-(2-nitrobenzyl)amine trihydrochloride;
- the commercial products of the oxime ketone ester system include any one or more of OXE02, PBG-304, OXE01 and PBG-30.
- the triazine compound is 2-(1,3-benzodioxolane-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine, PAG-201 , any one or more of PAG-202 and PAG-20101.
- the sensitizer is 4-hydroxybenzophenone and/or 4,4'-dihydroxybenzophenone;
- the sensitizer is usually used in conjunction with the photoinitiator, and its function is to reduce the degree of hydrogen bonding between the photoinitiator and the resin, and to improve the photosensitivity, the solubility difference, and the resolution. Rate.
- the reactive diluent is a methacrylate monomer or an alicyclic monomer having a heterocyclic structure.
- the alicyclic monomer with heterocyclic structure is any one or more of N-acryloyl morpholine, glycidyl methacrylate, 4-tert-butyl cyclohexyl acrylate and methyl oxetan acrylate. kind.
- the weight part of the reactive diluent is 5-10 parts.
- the solvent is diethylene glycol alkyl ether compound, dipropylene glycol alkyl ether compound, propylene glycol monoalkyl ether compound, propylene glycol monoalkyl ether acetate compound, N,N-dimethyl ether Any one or more of amide compounds, lactate compounds, ketones and 3-alkoxy propionate compounds;
- the auxiliary agent is any one or more of surfactants, defoaming agents, antioxidants and coupling agents.
- the diethylene glycol alkyl ether compound is any one or more of diethylene glycol dimethyl ether, diethylene glycol diethyl ether and diethylene glycol methyl ethyl ether; the dipropylene glycol
- the alkyl ether compound is dipropylene glycol dimethyl ether and/or dipropylene glycol diethyl ether;
- the propylene glycol monoalkyl ether compound is propylene glycol monomethyl ether and/or propylene glycol monoethyl ether;
- the compounds are N,N-dimethylformamide and/or N,N-dimethylacetamide;
- the lactate compounds are methyl lactate and/or ethyl lactate;
- the ketones are cyclobutanone and/or cyclopentanone;
- the 3-alkoxy propionate compounds are ethyl 3-methoxypropionate, propyl 3-methoxypropionate,
- the surfactant is a silicone-based surfactant
- the commercially available products include any of KP-341, KP-340, BYK-330, BYK-333, BYK-378 and BYK-340. one or more;
- fluorine-containing surfactants commercial products that can be listed are any one or more of R40, R42, R41, F443, F554, F556 and F563;
- the defoamer is a silicone-based defoamer, and commercial products that can be listed are BYK-020 and/or BYK-022;
- the antioxidant is a hindered phenolic antioxidant or a phosphite antioxidant, and the listed commercial products are 1010, 1076, 1024, 1098, BHT, CHEMNOX 168, CHEMNOX 626, CHEMNOX B225 and CHEMNOX B561 any one or more of them;
- the coupling agent is an organosilicon-type or melamine-type coupling agent, and the commercially available products include any one or several of KBM403, KBM503, Z-6040 and Z603.
- the present invention also provides a preparation method of a fluorine-containing resin composition, comprising the following steps:
- the raw materials are weighed in parts by weight according to the fluororesin composition, then stirred uniformly, and the obtained mixture is filtered through a 0.1-0.5 ⁇ m filter to obtain the fluororesin composition.
- the solid content concentration of the fluororesin composition is 10%-70%, preferably 15%-50%.
- a 0.2 ⁇ m filter is used for filtration.
- the present invention also provides a method for preparing a cured film, comprising the following steps:
- the fluororesin composition is coated on the surface of the substrate, soft baked, exposed to light, developed, irradiated with UV, and hardened to obtain the cured film.
- the material of the substrate is any one of metal plane, silicon wafer and glass, preferably glass; the film coating adopts any one of spray coating, spin coating and slit coating, preferably spin coating method; The thickness of the film is adjusted according to need, and the rotation speed is preferably 2 ⁇ m-5 ⁇ m as the planarizing insulating film.
- the soft-baking temperature is 90°C-130°C, and the time is 120s-200s.
- the purpose of soft baking is to remove the solvent in the film.
- the exposure amount is 80mJ-200mJ; in this process, a mask engraved with a certain pattern is used to cover the film, and radiation is used for irradiation, and the radiation used is selected from X-rays, electron beams and ultraviolet rays. any one, wherein ultraviolet light is preferred;
- the ultraviolet light used in the above exposure is any one or more of i-line (wavelength 365nm), g-line (wavelength 436nm) and far-ultraviolet (for example: KrF), wherein preferably i-line, g-line and i-line and g-line are mixed any of the rays.
- the specific operation of the development is to use a cleaning solvent to clean; wherein, the cleaning solvent is any aqueous solution in sodium hydroxide, potassium hydroxide and tetramethyl ammonium hydroxide, more preferably 2.38% tetramethyl ammonium hydroxide Aqueous ammonium solution; developing temperature is 23°C, time is 60s-120s.
- the cleaning solvent is any aqueous solution in sodium hydroxide, potassium hydroxide and tetramethyl ammonium hydroxide, more preferably 2.38% tetramethyl ammonium hydroxide Aqueous ammonium solution; developing temperature is 23°C, time is 60s-120s.
- the light intensity of the UV irradiation is 100-2000 mj/cm 2 ; more preferably 200-1000 mj/cm 2 .
- the beneficial effect of adopting the above technical scheme is that the remaining photoinitiator is completely destroyed, and the film is more fully cured in the process of hardening the film.
- the specific operation of hardening the film is to bake the developed film at 150°C-250°C.
- FIG. 1 accompanying drawing is the structural representation of the film uniformity evaluation of the cured film in the present invention
- FIG. 2 accompanying drawing is the schematic diagram of the insulation evaluation test box of the cured film in the present invention
- Figure 4-2 is a microscope image in the evaluation of the figure morphology in the present invention.
- Heating rate 10°C/min, heating up to 800°C
- Resin solid content take 1.0000g of resin solution, bake at 120°C for 2h and weigh, and take the average value of three parallel samples
- Solid content (drying weight/before-drying weight)*100%
- Example 4-13 and Comparative Example 3-4 are respectively the raw material ratio of the resin composition prepared by using the copolymer (A) alkali-soluble resin prepared in Example 1-3 and Comparative Example 1-2.
- Table 2 Among them, the resin compositions prepared in Examples 3-9 can be used for interlayer insulating films, the resin compositions prepared in Examples 7-8 can be used in chemically amplified interlayer insulating films, and Examples 12-13 can be used in OC films ;
- the specific steps of the preparation methods of the above-mentioned Examples 4-13 and Comparative Examples 3-4 are: dissolving the above-mentioned raw materials in a clean, yellow light environment, stirring and dissolving for 2 hours at a temperature of 20 ° C ⁇ 25 ° C, so that the pore size of 0.2 ⁇ m is exceeded.
- the resin composition was obtained by filtration through a membrane filter.
- the preparation methods of the cured films of Examples 14-23 are: a TFT glass substrate ( EAGLE XG) was coated with the resin composition solution prepared in Example 4-13 by using a rotary homogenizer, soft-baked at 110°C for 120s on a hot plate, and then used a MJB4 exposure machine made by SUSS to expose at 1000mj/cm 2 exposure, and then hardened the film in a clean oven at 230 °C for 40 min to form a 2 ⁇ m thick cured film on the TFT glass substrate.
- a TFT glass substrate EAGLE XG
- the light transmittance of the glass substrate having the cured film was measured at a wavelength in the range of 400 to 800 nm using a spectrophotometer [Shimadzu UV2600].
- a spectrophotometer Shiadzu UV2600.
- the transmittance T2 at 400 nm of the cured films was measured using a spectrophotometer [Shimadzu UV2600].
- the sample was cut into two pieces of the same size, soaked in N-methylpyrrolidone (NMP) and isopropanol (IPA) for 60 min at 25°C, and the solvent was blown off with an N2 air gun, and the 400 nm diameter of the cured film was measured respectively.
- NMP N-methylpyrrolidone
- IPA isopropanol
- Lines and lattice patterns at 5 ⁇ m have no residual film, the lines are clear and tidy, and the shape is considered to be good when the slope is 30 to 70 degrees. , see Figure 4-(1-2) for the SEM image and microscope photo of the embodiment.
- the exposed part of ITO and the Al electrode were connected to the LCR meter (Agilent 4284A), and the capacitance value C was measured at 0.1V, 100KHz at 25°C, and the dielectric constant was calculated according to the following formula:
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
一种含氟树脂组合物包括以下重量份数的原料:含化合物(I)的碱溶性树脂(A)、光引发剂、增感剂、活性稀释剂、溶剂、助剂;化合物(I)单体的结构式为:其中:R选自-CH=CH2、-C(CH3)=CH2、丙烯酰基或甲基丙烯酰基;R1、R1'、R2、R2'各自独立地选自:氢、羟基、C1-C4烷基或C1-C4烷氧基;R3选自氢或C1-C6烷基;A环选自环己基或苯基;B环选自苯基、萘基或蒽基。这样的含氟树脂组合物具有良好的涂布性能,电绝缘性和光透过性,同时具有更好的耐化学性、耐热性、硬度以及更优的附着力。
Description
本发明涉及树脂合成技术领域,更具体的说是涉及一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法。
随着彩色液晶显示器的普及,人们对液晶显示器彩色显示的要求也在不断提高。彩色滤光片和薄膜晶体管是液晶显示器实现彩色显示的关键部件,其表面的平整度和光透过率直接影响着显示器的性能。
为了提高彩色滤光片的性能,可在彩色滤光片制作中,在滤光膜形成表面再旋涂一层树脂材料的固化膜保护层,即:OC膜(Over Coat),用以提高彩色滤光膜表面的平整度和光透过性,同时要求具有较好的耐热性和强度以保护滤光膜不受损坏,提高使用寿命。同样,在薄膜晶体管(TFT)型液晶显示元件中通常使用固化膜作为层间绝缘膜覆盖TFT元件,层间绝缘膜主要作用为各膜层间绝缘、保护及平坦化。
随着显示器高亮度、大型化、高响应的发展趋势以及显示器件中膜形成工艺的不断改进,就要求形成固化膜的树脂组合物具有良好的涂布性能,更高的电绝缘性和光透过性,同时具有更好的耐化学性、耐热性、硬度以及更优的附着力,以满足需求。
因此,开发一种可用于液晶显示器彩色滤光片保护膜(OC膜)和薄膜晶体管(TFT)层间绝缘膜等固化膜材料的树脂组合物是本领域技术人员亟需解决的问题。
发明内容
有鉴于此,本发明提供了一种具有良好的涂布性能,电绝缘性和光透过性,同时具有更好的耐化学性、耐热性、硬度以及更优的附着力的含氟树脂组合物及制备方法。
为了实现上述目的,本发明采用如下技术方案:一种含氟树脂组合物,包括以下重量份数的原料:含化合物(I)的碱溶性树脂(A)18-42份、光引发剂2-8份、增感剂0.3-1.2份、活性稀释剂0-15份、溶剂60-90份、助剂1-8份;
所述化合物(I)单体的结构式为:
其中:R选自-CH=CH
2、-C(CH
3)=CH
2、丙烯酰基或甲基丙烯酰基;
R
1、R
1'、R
2、R
2'各自独立地选自:氢、羟基、C1-C4烷基或C1-C4烷氧基;
R
3选自氢或C1-C6烷基;
A环选自环己基或苯基;
B环选自苯基、萘基或蒽基。
本发明的有益效果:本发明中的含氟树脂组合物具有良好的涂布性能,电绝缘性和光透过性,同时具有更好的耐化学性、耐热性、硬度以及更优的附着力的。
优选地,化合物(I)单体的结构式为以下结构式中的任一种:
优选地,所述碱溶性树脂(A)的制备方法为:向三口瓶中加入化合物(I)单体2-5份、丙烯酸单体1-5份、丙烯酸酯单体10-30份、马来酰亚胺单体2-5份、引发剂1-5份、分子量调节剂0.2-1.0份和有机溶剂50-84份混合搅拌升温至75-80℃,保温反应3-6h,冷却降温至室温终止反应,得到所述碱溶性树脂(A);其中,所述化合物(I)的使用量按照碱溶性树脂(A)的固含量折算添加8%~15%;
优选地,所述丙烯酸单体为甲基丙烯酸;所述丙烯酸酯单体为甲基丙烯酸甲酯、甲基丙烯酸月桂醇酯、甲基丙烯酸四氢糠酯和甲基丙烯酸缩水甘油酯中的一种或几种;所述马来酰亚胺单体为N-环己基马来酰亚胺;所述引发剂为偶氮二异庚腈;所述分子量调节剂为α-甲基苯乙烯二聚物。
优选地,所述光引发剂为由酚类化合物与215-叠氮萘醌磺酰氯按照摩尔比为1:0.5-1:4经缩合反应得到;其中,光引发剂相对于酚类化合物中羟基数选用料比为50%~100%摩尔比的215-叠氮萘醌磺酰氯进行缩合。
优选地,所述酚类化合物为4-羟基二苯甲酮,2,4-二羟基二苯甲酮、2,4,6-三羟基二苯甲酮,2,3,4-三羟基二苯甲酮、2,2’,4,4’-四羟基二苯甲酮,2,3,4,4’-四羟基二苯甲酮、2,3,4,2’,6’-五羟基二苯甲酮、2,3,4,3’,4’,5’-六羟基二苯甲酮、3,4,5,3’,4’,5’-六羟基二苯甲酮、双酚A、螺双茚满、甲酚三聚体、三(4-羟基苯基)甲烷,1,1,1,-三(四羟基苯基)乙烷,1,1,1,-三(4-羟基苯基)丙烷、1,1,1,-三(4-羟基苯基)丁烷、1,1,-二(4-羟基苯基)环己烷及α,α,α'-三(4-羟苯基)-1-乙基-4-异丙苯中的任一种或几种。
更加优选地,
上述B-1(4-羟基二苯甲酮)、B-2(4,4’-二羟基二苯甲酮)、B-3(2,4-二羟基二苯甲酮)、B-4(2,3,4-三羟基二苯甲酮)、B-5(2,3,4,4’-四羟基二苯甲酮)、B-6(螺双茚满)、B-7(甲酚三聚体)、B-8(双酚A);
该类光引发剂的显影机理为:混配过程光引发剂中的叠氮结构与树脂中的羟基、羧基形成氢键,导致树脂的碱溶性降低,而在紫外光照下叠氮萘醌基团释放N
2,并发生重排生成茚酸,生成的氢键被破坏,产品光照部分再一次转变为碱溶性,而非光照区不溶解,形成溶解差异性。
更加优选地,光引发剂为B-4、B-5和B-8中的一种与215-叠氮萘醌磺酰氯经缩合反应得到,更优选B-8与215-叠氮萘醌磺酰氯按照摩尔比(1:0.5)-(1:4)经缩合反应得到。
可列举的商用化产品有NT-200、NT-250、4NT-250、4NT-300、4NT-350、TPPA-200和TPPA-250(东洋合成)中的任一种或几种。
优选地,所述光引发剂为磷盐系、碘鎓盐系、邻硝基苄基盐系、肟酮酯系和三嗪系化合物中的任一种或几种。
更加优选地,所述磷盐系为苯硫基苯基二苯基硫鎓六氟磷酸盐和/或双(4,4’-硫醚三苯基硫鎓)六氟磷酸盐;
所述碘鎓盐系为双噻吩环碘鎓盐、芴酮基苯基碘鎓盐和聚苯乙烯碘锗-六氟锑酸盐中的任一种或几种;
所述邻硝基苄基盐系为N,N-二(2-氨基乙基)-N-(2-硝基苄基)胺三盐酸盐;
所述肟酮酯系可列举的商用化产品有OXE02、PBG-304、OXE01和PBG-30中的任一种或几种。
所述三嗪系化合物为2-(1,3-苯并二氧戊环-5-基)-4,6-双(三氯甲基)-1,3,5-三嗪、PAG-201、PAG-202和PAG-20101中的任一种或几种。
优选地,所述增感剂为4-羟基二苯甲酮和/或4,4’-二羟基二苯甲酮;
采用上述技术方案的有益效果:增感剂通常与光引发剂配合使用,其作用为降低光引发剂与树脂之间的氢键结合度,并提高光感敏度,增强溶解差异性,提高分辨率。
所述活性稀释剂为甲基丙烯酸酯类单体或具有杂环结构的脂环族单体。
更加优选地,活性稀释剂为5-10份。其中,所述甲基丙烯酸酯类为甲基丙烯酸羟乙酯、甲基丙烯酸苄酯、季戊四醇三丙烯酸酯、双季戊四醇五丙烯酸酯、双季戊四醇六丙烯酸酯、丙氧基丙三醇三丙烯酸酯、苯氧乙基甲基丙烯酸酯、三羟甲基丙烷三丙烯酸酯和1,6己二醇二丙烯酸酯中的任一种或几种;
所述具有杂环结构的脂环族单体为N-丙烯酰吗啉、甲基丙烯酸缩水甘油酯、4-叔丁基环己基丙烯酸酯和氧杂环丁基丙烯酸甲酯中的任一种或几种。
所述活性稀释剂的重量份数为5-10份。
优选地,所述溶剂为二乙二醇烷基醚类化合物、二丙二醇烷基醚类化合物、丙二醇单烷基醚类化合物、丙二醇单烷基醚乙酸酯化合物、N,N-二甲基酰胺类化合物、乳酸酯类化合物、酮类和3-烷氧基丙酸酯类化合物中的任一种或几种;
所述助剂为表面活性剂、消泡剂、抗氧剂和偶联剂中的任一种或几种。
更加优选地,所述二乙二醇烷基醚类化合物为二乙二醇二甲醚、二乙二醇二乙醚和二乙二醇甲乙醚中的任一种或几种;所述二丙二醇烷基醚类化合物为二丙二醇二甲醚和/或二丙二醇二乙醚;所述丙二醇单烷基醚类化合物为丙二醇单甲醚和/或丙二醇单乙醚;所述N,N-二甲基酰胺类化合物为N,N-二甲基甲酰胺和/或N,N-二甲基乙酰胺;所述乳酸酯类化合物为乳酸甲酯和/或乳酸乙酯;所述酮类为环丁酮和/或环戊酮;所述3-烷氧基丙酸酯类化合物为3-甲氧基丙酸乙酯,3-甲氧基丙酸丙酯,3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸丙酯和二乙二醇单丁基醚醋酸酯中的任一种或几种。
更加优选地,所述表面活性剂为有机硅类表面活性剂,可列举的商用化产品有KP-341、KP-340、BYK-330、BYK-333、BYK-378和BYK-340中的任一种或几种;
或,含氟类表面活性剂,可列举的商用化产品有R40、R42、R41、F443、F554、F556和F563中的任一种或几种;
所述消泡剂为有机硅类消泡剂,可列举的商用化产品有BYK-020和/或BYK-022;
所述抗氧剂为为受阻酚类抗氧剂或亚磷酸酯类抗氧剂,可列举的商用化产品有1010、1076、1024、1098、BHT、CHEMNOX 168、CHEMNOX 626、CHEMNOX B225和CHEMNOX B561中的任一种或几种;
所述偶联剂为有机硅类或三聚氰胺类偶联剂,可列举的商用化产品有KBM403、KBM503、Z-6040和Z603中的任一种或几种。
本发明中还提供了一种含氟树脂组合物的制备方法,包括以下步骤:
按照含氟树脂组合物称取各重量份数的原料,然后搅拌均匀,将得到的混合物用0.1~0.5μm的滤膜过滤,得到所述的含氟树脂组合物。
优选地,含氟树脂组合物的固体成分浓度为10%-70%,优选的为15%-50%。
优选地,采用0.2μm的滤膜过滤。
本发明中还提供了一种固化膜的制备方法,包括以下步骤:
将含氟树脂组合物涂布于基板表面,软烘,曝光,显影,UV照射,坚膜,得到所述固化膜。
优选地,基板材质为金属平面、硅片、玻璃中的任一种,优选为玻璃;薄膜涂布采取喷涂、旋涂、狭缝涂布中的任一种,优选为旋涂法;所形成的膜厚度根据需要进行调整转速,作为平坦化绝缘膜优选2μm-5μm。
优选地,所述软烘温度为90℃-130℃,时间120s-200s。
采用上述技术方案的有益效果:软烘目的主要是去除薄膜中的溶剂。
优选地,所述曝光量为80mJ-200mJ;本工序中使用刻有一定图案性状的掩模对薄膜进行覆盖,使用射线进行照射,所使用的射线选自X-射线、电子束和紫外线中的任一种,其中优选紫外线;
上述曝光使用的紫外线为i线(波长365nm)、g线(波长436nm)和远紫外(例如:KrF)中的任一种或几种,其中优选i线、g线和i线与g线混合射线中的任一种。
优选地,所述显影的具体操作为采用清洗溶剂清洗;其中,清洗溶剂为氢氧化钠、氢氧化钾和四甲基氢氧化铵中的任一种水溶液,更优选2.38%四甲基氢氧化铵水溶液;显影温度为23℃,时间为60s-120s。
优选地,所述UV照射的光强为100-2000mj/cm
2;更加优选地为200-1000mj/cm
2。
采用上述技术方案的有益效果:彻底破坏剩余的光引发剂,试坚膜过程中膜固化更加充分。
优选地,所述坚膜的具体操作为将显影后的薄膜在150℃-250℃下烘烤。
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据提供的附图获得其他的附图。
图1附图为本发明中固化膜的膜均匀评价的结构示意图;
图2附图为本发明中固化膜的的绝缘性评价测试盒子示意图;
附图3附图为本发明中膜耐热性的评价中的TGA图;
附图4-1附图为本发明中图形形貌的评价中的SEM图;
附图4-2附图为本发明中图形形貌的评价中的显微镜图。
下面将结合本发明实施例中的附图,对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
碱溶性树脂A-1的合成,具体步骤如下:
氮气保护下,向三口瓶中加入二乙二醇二乙醚22.0kg,甲基丙烯酸1.0kg,甲基丙烯酸甲酯1.0kg,甲基丙烯酸四氢糠酯6kg,化合物I-21.0kg,N-环己基马来酰亚胺1.0kg,偶氮二异丁腈0.5kg,α-甲基苯乙烯二聚物0.5kg;搅拌下升温至78℃,保温反应4h,冷却降温至室温终止反应。
实施例2
碱溶性树脂A-2的合成,具体步骤如下:
氮气保护下,向三口瓶中加入二乙二醇二甲醚22.0kg,甲基丙烯酸1.0kg,甲基丙烯酸月桂醇酯0.5kg,甲基丙烯酸缩水甘油酯6kg,甲基丙烯酸二环戊基酯0.5kg,化合物I-251.0kg,N-环己基马来酰亚胺1.0kg,偶氮二异庚腈0.5kg,α-甲基苯乙烯二聚物0.5kg;搅拌下升温至78℃,保温反应4h,冷却降温至室温终止反应。
实施例3
碱溶性树脂A-3的合成,具体步骤如下:
氮气保护下,向三口瓶中加入二乙二醇甲乙醚22.0kg,甲基丙烯酸1.0kg,甲基丙烯酸月桂醇酯0.5kg,甲基丙烯酸缩水甘油酯4kg,甲基丙烯酸四氢糠基酯2kg,甲基丙烯酸二环戊基酯0.5kg,化合物I-261.0kg,N-环己基马来酰 亚胺1.0kg,偶氮二异庚腈0.5kg,α-甲基苯乙烯二聚物0.5kg;搅拌下升温至78℃,保温反应4h,冷却降温至室温终止反应。
对比例1
共聚物A-4的合成,具体步骤如下:
氮气保护下,向三口瓶中加入二乙二醇甲乙醚22.0kg,甲基丙烯酸1.0kg,甲基丙烯酸月桂醇酯0.5kg,甲基丙烯酸缩水甘油酯4kg,甲基丙烯酸四氢糠基酯2kg,甲基丙烯酸二环戊基酯0.5kg,4-羟基苯基甲基丙烯酸酯1.0kg,N-环己基马来酰亚胺1.0kg,偶氮二异庚腈0.5kg,α-甲基苯乙烯二聚物0.5kg;搅拌下升温至78℃,保温反应4h,冷却降温至室温终止反应。
其中,替换CF
2O单体。
对比例2
共聚物A-5的合成,具体步骤如下:
氮气保护下,向三口瓶中加入二乙二醇甲乙醚22.0kg,甲基丙烯酸1.0kg,甲基丙烯酸月桂醇酯0.5kg,甲基丙烯酸缩水甘油酯4kg,甲基丙烯酸四氢糠基酯2kg,甲基丙烯酸二环戊基酯0.5kg,4’-叔丁氧基-(1,1’-联苯基)-甲基丙烯酸酯1.0kg,N-环己基马来酰亚胺1.0kg,偶氮二异庚腈0.5kg,α-甲基苯乙烯二聚物0.5kg。搅拌下升温至78℃,保温反应4h,冷却降温至室温终止反应。
其中,替换CF
2O单体。
1、关于聚合物(A)碱溶性树脂的检测
(1)GPC
仪器:waters(515-2414)
凝胶柱:岛津KF801+KF802+KF803
溶剂:THF
流速:0.8ml/min
(2)透过率
仪器:岛津UV-2600
测定方式:透射率
波长范围200nm-800nm
(3)TGA
仪器:美国TA TGA-Q50
升温速率:10℃/min,升温至800℃
(4)树脂固含量:取树脂溶液1.0000g,120℃烘2h称重,平行三次测样取平均值
固含量=(烘干重量/烘前重量)*100%
聚合物(A)性能测试结果如下(表1):
聚合物 | TGA | 透过率 | 固含量 | 粘度 | 分子量Mw |
A-1 | 252.9℃ | 95.4% | 28.2% | 68cP | 12800 |
A-2 | 255.3℃ | 95.8% | 27.8% | 58cP | 10200 |
A-3 | 257.4℃ | 96.5% | 28.4% | 65cP | 12400 |
A-4 | 242.0℃ | 96.4% | 27.5% | 60cP | 10800 |
A-5 | 255.6℃ | 90.1% | 28.0% | 65cP | 11600 |
实施例4-13及对比例3-4分别为采用实施例1-3和对比例1-2中制得的共聚物(A)碱溶性树脂制得的树脂组合物的原料配比如下表2中,其中,实施例3-9制得树脂组合物可用于层间绝缘膜,实施例7-8制得树脂组合物可用于化学增幅型层间绝缘膜,实施例12-13可用于OC膜;
表2-1 实施例4-13和对比例3-4制备树脂组合物的原料(单位kg)
上述实施例4-13及对比例3-4的制备方法的具体步骤均为:将上述各原料在洁净、黄光环境中溶解,控温20℃~25℃搅拌溶解2h,使过0.2μm孔径的过膜器过滤,制得树脂组合物。
实施例14-23的固化膜的制备方法为:在100mm×100mm×0.7mm的TFT玻璃基板(
EAGLE XG)上使用旋转匀胶机涂布实施例4-13制备的树脂组合物溶液,在热板上110℃下软烘120s,再使用SUSS制造的MJB4曝光机,以1000mj/cm
2的曝光量进行曝光,然后在洁净烘箱中230℃下坚膜40min,在TFT玻璃基板上形成2μm厚的固化膜。
对比例5-6的固化膜的制备方法同实施例14-23。
固化膜物性评价
1、固化膜表面的评价
对实施例14-23和对比例5-6的膜表面照射钠灯,目测膜面的平整度,结果见表3。
2、膜均匀性的评价
针对于实施例14-23和对比例5-6的膜,在覆有膜面的基板上选取1cm×1cm区域,取九个点(如图1);
使用VASE椭偏仪(美国J.A.Woollam公司,VB-400)分别测定不同点的的膜厚,按照以下公式计算膜均匀度:
在试样表面三个不同部位进行测定,取平均值,当膜均匀度≤2.0%时记作A,2.0%~4.0%时记作B,≥4.0%时记作C,结果见表3。
3、膜附着力的评价
针对于实施例14-23和对比例5-6的膜;将上述覆膜基板膜面朝上放置在坚硬、平直的物面上,使用划格试验器(BYK 5123刀齿数11,刀齿间距1mm),握住切割刀具,使刀垂直于样板表面,均匀施力,以平稳的手法划出平行的11条切割线;再与原先的切割线成90°角垂直交叉划出平行的11条切割线,形成网格图形,所有的切口均需穿透到基板的表面;用软毛刷沿着网格图形的每一条对角线,轻轻地向后扫几次,再向前扫几次;在膜面上施加胶带(3M610胶带),除去胶带最前面一段,然后剪下长约75mm的胶带,将其中心点放在网格上方压平,胶带长度至少超过网格20mm,并确保其与膜面完全接触;在贴上胶带5min内,拿住胶带悬空的一端,并以与膜面尽可能成60°的角度,在0.5~1.0s内平稳地将胶带撕离,然后用显微镜观察膜面脱落的情况;在试样表面三个不同部位进行试验,记录划格试验等级。
当切割边缘完全平滑,无一格脱落,记作A;当在切口交叉处膜层有少许分离,划格区受影响不大于5%,记作B;当划格区受影响大于5%,记作C,结果见表3。
4、膜硬度的评价
针对于实施例14-23和对比例5-6的膜;将上述覆膜基板膜面朝上放置在坚硬、平直的物面上,用一组符合GB 149高级绘图铅笔,即铅笔等级6H、 5H、4H、3H、2H、H、HB,B、2B、3B、4B、5B、6B,使其笔芯露出4~6mm,垂直砂纸打磨直至端面平整,边缘锐利为宜。用便携式铅笔法硬度计(QHO-A),从6H铅笔开始,用力向前推进,每级铅笔划5次,每级若有2次膜层划破,更换另一等级的铅笔,至少有4次不能划破膜层的铅笔为止,记录相应硬度值,结果见表3。
5、膜透过率的评价
针对于实施例14-23和对比例5-6的膜;使用分光光度计[岛津UV2600],在400~800nm范围的波长下测定具有该固化膜的玻璃基板的光线透过率。该最低光线透过率的值在95%以上时,认为透明性良好,结果见表3。
6、膜耐热性的评价
针对于实施例14-23和对比例5-6的膜;固化膜剥离,TGA测试其5%失重温度,结果见表3,实施例的TGA图见附图3。
7、膜耐溶剂性的评价
针对于实施例14-23和对比例5-6的膜;使用分光光度计[岛津UV2600]测定该固化膜400nm处透过率T2。接着,将样品裁切成大小相同的两片,分别浸泡在25℃,N-甲基吡咯烷酮(NMP)和异丙醇(IPA)中60min,N2气枪吹去溶剂后,分别测定固化膜的400nm处透过率T
NMP和T
IPA,按照以下公式计算固化膜耐溶剂透过变化率:
固化膜耐溶剂透过变化率结果见表3,该值在2%以下时,认为耐溶剂性良好。
8、膜耐碱性的评价
针对于实施例14-23和对比例5-6的膜;测定固化膜的膜厚T3,接着将样片浸泡在25℃,5%的氢氧化钾水溶液中60min后,用超纯水清洗膜层,N2气枪吹干,测定固化膜膜厚T3’,按照以下公式计算耐碱性膜厚变化率:
耐碱性膜厚变化率结果见表3,该值在5%以下时,认为耐碱性良好。
9、敏感度的评价
在100mm×100mm×0.7mm的TFT玻璃基板(
EAGLE XG)上使用旋转匀胶机涂布制备的实施例4-13及对比例3-4树脂组合物溶液,在热板上110℃下软烘120s,形成厚2.2μm的膜。使用SUSS制造的MJB4曝光机,改变曝光时间,插入具有不同分辨率和图形的掩膜版对膜层进行曝光,接着,使用2.38%质量分数的四甲基氢氧化铵水溶液(显影液),使用静态法在25℃下进行显影处理,显影时间60s,显影后用超纯水清洗膜层,并用N
2气枪吹干,在洁净烘箱中230℃下坚膜40min,在玻璃基板上形成图案。进过曝光-显影-坚膜处理后,测定5μm处图案完全显影所需的曝光量,该数值作为敏感度,测定结果见,该值小于100mj/cm
2时,认为光敏度良好。
10、图形形貌的评价
与上述敏感度评价的制备方法相同,其中,以敏感度的评价中所需曝光量在玻璃基板上形成膜厚2μm的图案。这样形成的图案用扫描式电子显微镜(SEM)观察其形状。
5μm处线条及点阵图形无残膜,线条清晰整齐,且坡度在30~70度时,认为形状良好。,实施例的SEM图和显微镜照片见附图4-(1-2)。
[绝缘性的评价]
按照以图2中制作测试盒子;
I在覆有ITO膜的50mm×50mm玻璃基材上使用旋转匀胶机涂布制备的树脂组合物溶液,在热板上在热板上110℃下软烘120s,形成膜层。
II使用曝光机(德国SUSS,MJB4,GHI混合线),以100mj/cm
2曝光量,插入所示图形掩膜版对膜层进行曝光。接着使用2.38%质量分数的四甲基氢氧化铵水溶液(显影液),使用静态法在25℃下进行显影处理,显影时间60s。 显影后用超纯水清洗膜层,并用N
2气枪吹干,在洁净烘箱中230℃下坚膜40min,在基板上形成膜厚2μm的边缘ITO裸露的40mm×40mm固化膜,使用VASE椭偏仪(美国J.A.Woollam公司,VB-400)测定膜厚d(m)。
III图示位置使用真空蒸镀装置(沈阳市超高真空应用技术研究所)在固化膜上形成5mm×5mm Al电极(S=7.85×10
-5m
2)。接着,ITO裸露部分和Al电极连接到LCR仪表(安捷伦4284A),25℃下,以0.1V,100KHz测得电容值C,按照如下公式计算介电常数:
介电常数结果见表3,该值在3.3以下时,认为绝缘性良好。
表3 实施例14-23和对比例5-6制得的固化膜的性能从测试结果
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言,由于其与实施例公开的方法相对应,所以描述的比较简单,相关之处参见方法部分说明即可。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (10)
- 根据权利要求1所述的一种含氟树脂组合物,其特征在于,所述碱溶性树脂(A)的制备方法为:向三口瓶中加入化合物(I)单体2-5份、丙烯酸单体1-5份、丙烯酸酯单体10-30份、马来酰亚胺单体2-5份、引发剂1-5份、分子量调节剂0.2-1.0份和有机溶剂50-84份混合搅拌升温至75-80℃,保温反应3-6h,冷却降温至室温终止反应,得到所述碱溶性树脂(A)。
- 根据权利要求1所述的一种含氟树脂组合物,其特征在于,所述光引发剂由酚类化合物与215-叠氮萘醌磺酰氯按照摩尔比为(1:0.5)-(1:4)经缩合反应得到。
- 根据权利要求3所述的一种含氟树脂组合物,其特征在于,所述酚类化合物为4-羟基二苯甲酮,4,4’-二羟基二苯甲酮、2,4-二羟基二苯甲酮、2,4,6-三羟基二苯甲酮,2,3,4-三羟基二苯甲酮、2,2’,4,4’-四羟基二苯甲酮,2,3,4,4’-四羟基二苯甲酮、2,3,4,2’,6’-五羟基二苯甲酮、2,3,4,3’,4’,5’-六羟基二苯甲酮、3,4,5,3’,4’,5’-六羟基二苯甲酮、双酚A、螺双茚满、甲酚三聚体、三(4-羟基苯基)甲烷,1,1,1,-三(四羟基苯基)乙烷,1,1,1,-三(4-羟基苯基)丙烷、1,1,1,-三(4-羟基苯基)丁烷、1,1,-二(4-羟基苯基)环己烷及α,α,α'-三(4-羟苯基)-1-乙基-4-异丙苯中的任一种或几种。
- 根据权利要求1所述的一种含氟树脂组合物,其特征在于,所述光引发剂为磷盐系、碘鎓盐系、邻硝基苄基盐系、肟酮酯系和三嗪系化合物中的任一种或几种。
- 根据权利要求1所述的一种含氟树脂组合物,其特征在于,所述增感剂为4-羟基二苯甲酮和/或4,4’-二羟基二苯甲酮;所述活性稀释剂为甲基丙烯酸酯类单体或具有杂环结构的脂环族单体。
- 根据权利要求1所述的一种含氟树脂组合物,其特征在于,所述溶剂为二乙二醇烷基醚类化合物、二丙二醇烷基醚类化合物、丙二醇单烷基醚类化合物、丙二醇单烷基醚乙酸酯化合物、N,N-二甲基酰胺类化合物、乳酸酯类化合物、酮类和3-烷氧基丙酸酯类化合物中的任一种或几种;所述助剂为表面活性剂、消泡剂、抗氧剂和偶联剂中的任一种或几种。
- 一种含氟树脂组合物的制备方法,其特征在于,包括以下步骤:按照权利要求1-7任一项所述的含氟树脂组合物称取各重量份数的原料,然后搅拌均匀,将得到的混合物用0.1~0.5μm的滤膜过滤,得到所述含氟树脂组合物。
- 一种固化膜的制备方法,其特征在于,包括以下步骤:将权利要求1-7任一项所述的含氟树脂组合物或采用权利要求8的制备方法制得的含氟树脂组合物涂布于基板表面,软烘,曝光,显影,UV照射,坚膜,得到所述固化膜。
- 根据权利要求9所述的一种固化膜的制备方法,其特征在于,所述软烘温度为90℃-130℃,时间120s-200s;所述曝光量为80mJ-200mJ;所述显影的具体操作为采用清洗溶剂清洗;所述UV照射的光强为100-2000mj/cm 2;所述坚膜的具体操作为将显影后的薄膜在150℃-250℃下烘烤。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17/754,068 US20230194984A1 (en) | 2020-12-30 | 2021-09-27 | Fluorine-containing resin composition and preparation method thereof, and preparation method of cured film containing same |
ZA2022/09401A ZA202209401B (en) | 2020-12-30 | 2022-08-22 | Fluorine-containing resin composition, preparation method therefor, and preparation method for cured film containing same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011612200.4 | 2020-12-30 | ||
CN202011612200.4A CN112731765B (zh) | 2020-12-30 | 2020-12-30 | 一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022142537A1 true WO2022142537A1 (zh) | 2022-07-07 |
Family
ID=75610300
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2021/120972 WO2022142537A1 (zh) | 2020-12-30 | 2021-09-27 | 一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US20230194984A1 (zh) |
CN (1) | CN112731765B (zh) |
WO (1) | WO2022142537A1 (zh) |
ZA (1) | ZA202209401B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112745453B (zh) * | 2020-12-30 | 2022-05-03 | 西安瑞联新材料股份有限公司 | 一种含氟丙烯酸树脂及其制备方法和应用 |
CN112731765B (zh) * | 2020-12-30 | 2024-03-26 | 西安瑞联新材料股份有限公司 | 一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 |
CN114736557B (zh) * | 2022-05-17 | 2023-06-27 | 广东希贵光固化材料有限公司 | 一种能深冲加工的胶印led印铁油墨及其制备方法 |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030087184A1 (en) * | 2001-09-13 | 2003-05-08 | Matsushita Electric Industrial Co., Ltd. | Pattern formation material and pattern formation method |
CN102207681A (zh) * | 2010-03-29 | 2011-10-05 | 新日铁化学株式会社 | 碱显影性感光性树脂组合物、及使用其而形成的适合显示元件的间壁、以及显示元件 |
WO2013024764A1 (ja) * | 2011-08-12 | 2013-02-21 | ダイキン工業株式会社 | 撥液性硬化性インク組成物 |
CN104136971A (zh) * | 2013-06-18 | 2014-11-05 | Dic株式会社 | 液晶显示装置 |
CN104513145A (zh) * | 2013-09-29 | 2015-04-15 | 江苏和成新材料有限公司 | 2,3,5-三氟-4-二氟(3,4,5-三氟苯酚基)甲基-苯甲醛及其合成方法和在制备液晶化合物中的应用 |
US20150232757A1 (en) * | 2012-09-11 | 2015-08-20 | Dic Corporation | Liquid crystal display device |
CN107108795A (zh) * | 2014-10-24 | 2017-08-29 | Dic株式会社 | 含氟热分解性树脂、抗蚀剂组合物、滤色器保护膜用组合物、抗蚀膜及滤色器保护膜 |
CN107850693A (zh) * | 2015-12-03 | 2018-03-27 | 株式会社Lg化学 | 减反射膜 |
US20200124963A1 (en) * | 2017-08-31 | 2020-04-23 | Fujifilm Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, and method for manufacturing electronic device |
CN111154498A (zh) * | 2020-01-19 | 2020-05-15 | 西安瑞联新材料股份有限公司 | 一种含有1,5-茚满和二氟甲氧基桥的液晶化合物的制备方法 |
US20200183280A1 (en) * | 2017-08-31 | 2020-06-11 | Fujifilm Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, method for manufacturing electronic device |
US20200233301A1 (en) * | 2019-01-18 | 2020-07-23 | Sumitomo Chemical Company, Limited | Resin, resist composition and method for producing resist pattern |
CN112731765A (zh) * | 2020-12-30 | 2021-04-30 | 西安瑞联新材料股份有限公司 | 一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 |
CN112745453A (zh) * | 2020-12-30 | 2021-05-04 | 西安瑞联新材料股份有限公司 | 一种含氟丙烯酸树脂及其制备方法和应用 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6524699B2 (ja) * | 2015-02-24 | 2019-06-05 | Jnc株式会社 | ビニレン基を有する液晶性化合物、液晶組成物および液晶表示素子 |
JP6610057B2 (ja) * | 2015-07-29 | 2019-11-27 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
KR20170037196A (ko) * | 2015-09-25 | 2017-04-04 | 코오롱인더스트리 주식회사 | 유기 절연막용 감광성 수지 조성물 |
-
2020
- 2020-12-30 CN CN202011612200.4A patent/CN112731765B/zh active Active
-
2021
- 2021-09-27 US US17/754,068 patent/US20230194984A1/en active Pending
- 2021-09-27 WO PCT/CN2021/120972 patent/WO2022142537A1/zh active Application Filing
-
2022
- 2022-08-22 ZA ZA2022/09401A patent/ZA202209401B/en unknown
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030087184A1 (en) * | 2001-09-13 | 2003-05-08 | Matsushita Electric Industrial Co., Ltd. | Pattern formation material and pattern formation method |
CN102207681A (zh) * | 2010-03-29 | 2011-10-05 | 新日铁化学株式会社 | 碱显影性感光性树脂组合物、及使用其而形成的适合显示元件的间壁、以及显示元件 |
WO2013024764A1 (ja) * | 2011-08-12 | 2013-02-21 | ダイキン工業株式会社 | 撥液性硬化性インク組成物 |
US20150232757A1 (en) * | 2012-09-11 | 2015-08-20 | Dic Corporation | Liquid crystal display device |
CN104136971A (zh) * | 2013-06-18 | 2014-11-05 | Dic株式会社 | 液晶显示装置 |
CN104513145A (zh) * | 2013-09-29 | 2015-04-15 | 江苏和成新材料有限公司 | 2,3,5-三氟-4-二氟(3,4,5-三氟苯酚基)甲基-苯甲醛及其合成方法和在制备液晶化合物中的应用 |
CN107108795A (zh) * | 2014-10-24 | 2017-08-29 | Dic株式会社 | 含氟热分解性树脂、抗蚀剂组合物、滤色器保护膜用组合物、抗蚀膜及滤色器保护膜 |
CN107850693A (zh) * | 2015-12-03 | 2018-03-27 | 株式会社Lg化学 | 减反射膜 |
US20200124963A1 (en) * | 2017-08-31 | 2020-04-23 | Fujifilm Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, and method for manufacturing electronic device |
US20200183280A1 (en) * | 2017-08-31 | 2020-06-11 | Fujifilm Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, method for manufacturing electronic device |
US20200233301A1 (en) * | 2019-01-18 | 2020-07-23 | Sumitomo Chemical Company, Limited | Resin, resist composition and method for producing resist pattern |
CN111154498A (zh) * | 2020-01-19 | 2020-05-15 | 西安瑞联新材料股份有限公司 | 一种含有1,5-茚满和二氟甲氧基桥的液晶化合物的制备方法 |
CN112731765A (zh) * | 2020-12-30 | 2021-04-30 | 西安瑞联新材料股份有限公司 | 一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 |
CN112745453A (zh) * | 2020-12-30 | 2021-05-04 | 西安瑞联新材料股份有限公司 | 一种含氟丙烯酸树脂及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
ZA202209401B (en) | 2022-11-30 |
US20230194984A1 (en) | 2023-06-22 |
CN112731765A (zh) | 2021-04-30 |
CN112731765B (zh) | 2024-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2022142537A1 (zh) | 一种含氟树脂组合物及制备方法和包含其的固化膜的制备方法 | |
TWI540382B (zh) | 感光性樹脂組成物 | |
TWI403848B (zh) | 感光性樹脂組成物 | |
TWI403841B (zh) | 感光性樹脂組成物 | |
CN1734351B (zh) | 隔离物用感光性树脂组合物 | |
TW200811205A (en) | Curing resin composition and forming method of curing coating film | |
CN106483766B (zh) | 感光性树脂组合物及由其形成的光固化图案 | |
TWI738634B (zh) | 正型感光性樹脂組成物、硬化膜及顯示元件 | |
TW201802594A (zh) | 感光性矽氧烷組成物 | |
TWI471697B (zh) | 負型感光性樹脂組成物 | |
CN111148805B (zh) | 正型感光性硅氧烷组合物以及使用了其的固化膜 | |
TWI416254B (zh) | Photosensitive resin composition | |
JP4501665B2 (ja) | 感光性樹脂組成物 | |
TWI655501B (zh) | 負型感光性樹脂組成物、隔壁及光學元件 | |
TWI614579B (zh) | 負感光型樹脂組合物及由其製造的光固化圖案 | |
JP4786360B2 (ja) | 感光性樹脂組成物、lcd基板及びその製造方法 | |
TWI663477B (zh) | 正型感光性樹脂組成物 | |
TWI803587B (zh) | 感放射線性組合物、硬化膜及顯示元件 | |
CN107229188A (zh) | 感光性树脂组合物 | |
KR20210097173A (ko) | 아크릴 중합된 폴리실록산, 이를 포함하는 조성물 및 이를 사용하여 제조된 경화 막 | |
TW201005442A (en) | Low temperature curing photosensitive resin composition | |
JP3842750B2 (ja) | 感光性樹脂組成物 | |
TW201100954A (en) | Photosensitive resin composition and liquid crystal panel | |
JP5637024B2 (ja) | 感光性樹脂組成物およびその用途 | |
KR102658153B1 (ko) | 감방사선성 수지 조성물 및 그의 용도 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21913282 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 21913282 Country of ref document: EP Kind code of ref document: A1 |