WO2020045214A1 - Composition de résine et film durci obtenu à partir de cette dernière - Google Patents
Composition de résine et film durci obtenu à partir de cette dernière Download PDFInfo
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- WO2020045214A1 WO2020045214A1 PCT/JP2019/032782 JP2019032782W WO2020045214A1 WO 2020045214 A1 WO2020045214 A1 WO 2020045214A1 JP 2019032782 W JP2019032782 W JP 2019032782W WO 2020045214 A1 WO2020045214 A1 WO 2020045214A1
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- Prior art keywords
- group
- resin composition
- polysiloxane
- mol
- general formulas
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- 239000011342 resin composition Substances 0.000 title claims abstract description 65
- -1 polysiloxane Polymers 0.000 claims abstract description 236
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 98
- 239000002904 solvent Substances 0.000 claims abstract description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 239000002253 acid Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000011817 metal compound particle Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 238000003384 imaging method Methods 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 37
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 82
- 230000015572 biosynthetic process Effects 0.000 description 70
- 238000003786 synthesis reaction Methods 0.000 description 68
- 238000005259 measurement Methods 0.000 description 43
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 41
- 238000000034 method Methods 0.000 description 40
- 150000001875 compounds Chemical class 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 31
- 239000011248 coating agent Substances 0.000 description 28
- 238000000576 coating method Methods 0.000 description 28
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 239000002245 particle Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 108091034057 RNA (poly(A)) Proteins 0.000 description 20
- 239000000178 monomer Substances 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 17
- 238000011156 evaluation Methods 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 238000002834 transmittance Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000011161 development Methods 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 239000013522 chelant Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 9
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000001282 organosilanes Chemical group 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 5
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 5
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- KKYDYRWEUFJLER-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F KKYDYRWEUFJLER-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 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 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- LLGVQQLZYJJDBZ-UHFFFAOYSA-N trimethoxy(2,2,2-trifluoroethyl)silane Chemical compound CO[Si](OC)(OC)CC(F)(F)F LLGVQQLZYJJDBZ-UHFFFAOYSA-N 0.000 description 3
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- TYROLSMHVJMZOC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F TYROLSMHVJMZOC-UHFFFAOYSA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 241000501754 Astronotus ocellatus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000005520 diaryliodonium group Chemical group 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- 238000001029 thermal curing Methods 0.000 description 2
- HMVGCSCUAUZFLC-UHFFFAOYSA-N tri(propan-2-yloxy)-(2,2,2-trifluoroethyl)silane Chemical compound CC(C)O[Si](CC(F)(F)F)(OC(C)C)OC(C)C HMVGCSCUAUZFLC-UHFFFAOYSA-N 0.000 description 2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N p-Isopropylbenzyl alcohol Natural products CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical class CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- OAVPBWLGJVKEGZ-UHFFFAOYSA-N tributoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCCCC)(OCCCC)OCCCC)CCC2OC21 OAVPBWLGJVKEGZ-UHFFFAOYSA-N 0.000 description 1
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- UNKMHLWJZHLPPM-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CCO[Si](OCC)(OCC)COCC1CO1 UNKMHLWJZHLPPM-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- OHKFEBYBHZXHMM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CCC)OCC1CO1 OHKFEBYBHZXHMM-UHFFFAOYSA-N 0.000 description 1
- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- FVMMYGUCXRZVPJ-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)OCC1CO1 FVMMYGUCXRZVPJ-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- KPNCYSTUWLXFOE-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC(C)OCC1CO1 KPNCYSTUWLXFOE-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- PSUKBUSXHYKMLU-UHFFFAOYSA-N triethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OCC)(OCC)OCC)CCC2OC21 PSUKBUSXHYKMLU-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- KKFKPRKYSBTUDV-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CC(CC)OCC1CO1 KKFKPRKYSBTUDV-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-UHFFFAOYSA-N 0.000 description 1
- ZOWVSEMGATXETK-UHFFFAOYSA-N trimethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OC)(OC)OC)CCC2OC21 ZOWVSEMGATXETK-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/27—Compounds containing a nitrogen atom bound to two other nitrogen atoms, e.g. diazoamino-compounds
- C08K5/28—Azides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
Definitions
- the present invention relates to a resin composition, a cured film thereof, and a solid-state imaging device, an organic EL device, and a display device including the same.
- polysiloxane materials are known as highly transparent and low refractive index materials, and are widely used in liquid crystal displays, touch panels, solid-state imaging devices, and the like.
- a large amount of fluorine-containing siloxane compound and particles such as silica nanoparticles and hollow silica are added in order to reduce the refractive index.
- a decrease in heat resistance was unavoidable, and when the particles were processed into a pattern, fine irregularities on the surface and edges were unavoidable.
- a low-refractive-index material excellent in heat resistance and chemical resistance without addition of particles was strongly demanded.
- the present invention provides a resin composition which is a low refractive index material having excellent heat resistance, excellent chemical resistance, and excellent pattern workability without adding particles. With the goal.
- the present invention provides a resin composition containing (A) a polysiloxane and (B) a solvent, wherein the (A) polysiloxane has a structure represented by the following general formulas (1) to (3).
- a resin composition comprising at least one or more structures having at least one structure represented by the following general formulas (4) and (5).
- Y is an alicyclic or aromatic linking group having 5 to 10 carbon atoms.
- R 1 is a single bond or an alkylene group having 1 to 4 carbon atoms, and R 2 is independently hydrogen or 1 carbon atom.
- R 3 are independently an organic group having 1 to 8 carbon atoms, X is a hydrogen atom or an acid dissociable group, a is an integer of 1 to 3, and n is an integer of 1 to 10.
- FIG. 3 is a process chart showing an example of producing a cured film using the resin composition according to the embodiment of the present invention.
- FIG. 3 is a process chart showing an example of producing a cured film using the resin composition according to the embodiment of the present invention.
- FIG. 3 is a process chart showing an example of producing a cured film using the resin composition according to the embodiment of the present invention.
- the resin composition of the present invention has at least one structure represented by the following general formulas (1) to (3) and at least one structure represented by the following general formulas (4) to (5) It contains the polysiloxane contained above.
- the structures represented by (1) to (3) and at least one or more of the structures represented by (4) to (5) in the polysiloxane Since the alkali dissolution inhibiting effect due to the interaction between the photosensitizer and the silanol can be exhibited while enhancing the alkali solubility, the contrast between the exposed and unexposed portions before and after development can be increased, and a film having excellent resolution can be obtained.
- Y is an alicyclic or aromatic linking group having 5 to 10 carbon atoms.
- R 1 is a single bond or an alkylene group having 1 to 4 carbon atoms
- R 2 is independently hydrogen or 1 carbon atom.
- R 3 are independently an organic group having 1 to 8 carbon atoms
- X is a hydrogen atom or an acid dissociable group
- a is an integer of 1 to 3
- n is an integer of 1 to 10.
- R 1 is a single bond or an alkylene group having 1 to 4 carbon atoms
- R 2 is independently hydrogen or an alkyl group having 1 to 4 carbon atoms
- R 3 is independently an organic group having 1 to 8 carbon atoms
- alkylene group for R 1 examples include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, and a t-butylene group.
- alkyl group for R 2 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutoxy group, a t-butyl group, and the like.
- Examples of the organic group for R 3 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclohexyl group, a phenyl group, and a naphthyl group.
- X is a hydrogen atom or an acid dissociable group, and when there are a plurality of Xs, the Xs may be the same or different.
- the acid dissociable group is a group that dissociates in the presence of an acid to generate a polar group.
- the acid dissociable group has an acetal structure or a ketal structure which is relatively stable to alkali, and these are dissociated by the action of an acid. Specific examples include, but are not limited to, an alkoxycarbonyl group, an acetal group, a silyl group, and an acyl group.
- alkoxycarbonyl group examples include a tert-butoxycarbonyl group, a tert-amyloxycarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an i-propoxycarbonyl group, and the like.
- acetal group methoxymethyl group, ethoxyethyl group, butoxyethyl group, cyclohexyloxyethyl group, benzyloxyethyl group, phenethyloxyethyl group, ethoxypropyl group, benzyloxypropyl group, phenethyloxypropyl group, ethoxybutyl group, An ethoxyisobutyl group is exemplified.
- silyl group examples include a trimethylsilyl group, an ethyldimethylsilyl group, a methyldiethylsilyl group, a triethylsilyl group, an i-propyldimethylsilyl group, a methyldi-i-propylsilyl group, a tri-i-propylsilyl group, and tert-butyl.
- Examples include a dimethylsilyl group, a methyldi-tert-butylsilyl group, a tri-tert-butylsilyl group, a phenyldimethylsilyl group, a methyldiphenylsilyl group, and a triphenylsilyl group.
- acyl group examples include, for example, acetyl, propionyl, butyryl, heptanoyl, hexanoyl, valeryl, pivaloyl, isovaleryl, lauryloyl, myristoyl, palmitoyl, stearoyl, oxalyl, malonyl, succinyl Group, glutaryl group, adipoyl group, piperoyl group, suberoyl group, azeolaoyl group, sebacoil group, acryloyl group, propioloyl group, methacryloyl group, crotonoyl group, oleoyl group, maleoyl group, fumaroyl group, mesaconoyl group, camphoryl group, benzoyl group , Phthaloyl, isophthaloyl, terephthaloyl, naphthoyl, toluoyl, hydroatropoyl, atrop
- the structures represented by the general formulas (1) to (3) are preferably the structures represented by the following general formulas (6) to (8).
- the compatibility between the photosensitive agent and the siloxane is improved, so that it is possible to prevent the film from becoming cloudy due to phase separation at the time of thermosetting, and to form a cured film without impairing the transparency.
- a is an integer of 1 to 3, but from the viewpoint of solubility and chemical resistance, a is preferably 1 to 2, and more preferably a.
- * indicates a bond directly connected to R 1 .
- R 1 is a single bond, it represents a bond directly connected to a silicon atom.
- These structures are preferably contained in the polysiloxane (A) in an amount of 5 to 50 mol%, more preferably 5 to 30 mol%.
- the content ratio of the organosilane units represented by the general formulas (1) to (3) can be determined by measuring 29 Si-NMR of polysiloxane, and determining the peak area of Si having an aromatic group bonded thereto and the ratio of the aromatic group being bonded. It can be determined from the ratio of the peak area of the Si derived from the untreated organosilane unit.
- organosilane units represented by the general formulas (1) to (3) can be identified using 1 H-NMR, 19 F-NMR, 13 C-NMR, IR, TOF-MS, and the like.
- R 2 independently represents hydrogen or an alkyl group having 1 to 4 carbon atoms.
- Specific examples of the siloxane having the structure represented by the general formula (4) or (5) include tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetraisopropoxysilane, tetrabutoxysilane, tetratertiarybutoxysilane, Methyl silicate 51 (manufactured by Fuso Chemical Industry Co., Ltd.), M silicate 51, silicate 40, silicate 45 (manufactured by Tama Chemical Industry Co., Ltd.), methyl silicate 51, methyl silicate 53A, ethyl silicate 48 (manufactured by Colcoat Co., Ltd.) and the like.
- a desirable content is 5 to 50 mol%, more preferably 5 to 30 mol%, in the polysiloxane that is a hydrolyzed condensate.
- the content ratio of the organosilane unit represented by the general formula (4) or (5) is determined by 1 H-NMR, 13 C-NMR, 29 Si-NMR, IR, TOF-MS, elemental analysis, ash measurement, and the like. Can be obtained in combination.
- the polysiloxane may further contain a structure represented by the following general formulas (9) to (11).
- R 2 is independently hydrogen or an alkyl group having 1 to 4 carbon atoms
- R 3 is independently an organic group having 1 to 8 carbon atoms
- R 4 is an organic group having 1 to 10 carbon atoms having a fluoro group. Represents a group.
- Specific examples of the fluorine-containing silane compound having the structure of the general formulas (9) to (11) include trifluoroethyltrimethoxysilane, trifluoroethyltriethoxysilane, trifluoroethyltriisopropoxysilane, and trifluoropropyltrisilane.
- triisopropoxysilane is used.
- the content in the polysiloxane (A) is preferably from 5 to 50 mol%, more preferably from 10 to 40 mol%, from the viewpoint of chemical resistance.
- the polysiloxane (A) used in the resin composition of the present invention may be copolymerized with another organosilane compound in addition to the above-mentioned organosilane compound.
- the copolymerizable organosilane compound examples include methyltrimethoxysilane, methyltriethoxysilane, methyltri (methoxyethoxy) silane, methyltripropoxysilane, methyltriisopropoxysilane, methyltributoxysilane, and ethyltrimethoxysilane.
- Ethyltriethoxysilane hexyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N- (2aminoethyl) -3-aminopropyltri Methoxysilane, 3-chloropropyltrimethoxysilane, 3- (N, N-glycidyl) aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, ⁇ -aminopropyl Trimethoxysilane, ⁇ -aminopropyltriethoxysilane, N- ⁇ - (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, ⁇ -cyanoethyltriethoxysilane
- acryloyl propyl methyl dimethoxy silane .gamma. acryloyl propyl methyl diethoxy silane, .gamma.-methacryloxypropyltrimethoxysilane such as acryloyl propyl (methoxyethoxy) silane.
- an organosilane compound having a hydrophilic group may be copolymerized as a raw material of the polysiloxane, if necessary.
- an organosilane compound having a hydrophilic group an organosilane compound having a carboxylic acid structure or an organosilane compound having a carboxylic acid anhydride structure is preferable, and an organosilane compound having a carboxylic acid anhydride structure is more preferable.
- organosilane compound having a carboxylic anhydride structure examples include an organosilane compound represented by any of the following formulas (12) to (14). Two or more of these may be used.
- R 5 to R 7 , R 9 to R 11 and R 13 to R 15 each represent an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a phenyl group.
- R 8 , R 12 and R 16 each represent a single bond or a linear aliphatic hydrocarbon group having 1 to 10 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms, and alkylcarbonyloxy having 2 to 6 carbon atoms.
- h and k represent an integer of 0 to 3.
- R 8 , R 12 and R 16 include —C 2 H 4 —, —C 3 H 6 —, —C 4 H 8 —, —O—, —C 3 H 6 OCH 2 CH (OH) Examples include CH 2 O 2 C—, —CO—, —CO 2 —, and —CONH—, and the following organic groups.
- organosilane compound represented by the general formula (12) include 3-trimethoxysilylpropylsuccinic anhydride, 3-triethoxysilylpropylsuccinic anhydride, and 3-triphenoxysilylpropylsuccinic anhydride. Things.
- organosilane compound represented by the general formula (13) include 3-trimethoxysilylpropylcyclohexyldicarboxylic anhydride.
- organosilane compound represented by the general formula (14) examples include 3-trimethoxysilylpropyl phthalic anhydride.
- the content of the component derived from the hydrolysis / condensation reaction product (siloxane compound) of the alkoxysilane compound in the resin composition is preferably at least 10% by mass, more preferably at least 20% by mass, based on the total solid content excluding the solvent. preferable. Further, the content is more preferably 80% by mass or less. By containing the siloxane compound in this range, the transmittance and crack resistance of the coating film can be further increased.
- the hydrolysis reaction is preferably carried out at room temperature to 110 ° C. for 1 to 180 minutes after adding an acid catalyst and water to the above alkoxysilane compound in a solvent over 1 to 180 minutes. By performing the hydrolysis reaction under such conditions, a rapid reaction can be suppressed.
- the reaction temperature is more preferably from 40 to 105 ° C.
- the reaction solution is preferably heated at 50 ° C. or higher and the boiling point of the solvent for 1 to 100 hours to conduct a condensation reaction. Further, in order to increase the degree of polymerization of the siloxane compound obtained by the condensation reaction, reheating or addition of a base catalyst can be performed.
- Various conditions for hydrolysis are to obtain physical properties suitable for the intended use by setting, for example, acid concentration, reaction temperature, reaction time, etc. in consideration of the reaction scale, the size and shape of the reaction vessel, etc. Can be.
- Examples of the acid catalyst used in the hydrolysis reaction include acid catalysts such as hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polycarboxylic acids or anhydrides thereof, and ion exchange resins. Particularly, an acidic aqueous solution using formic acid, acetic acid or phosphoric acid is preferable.
- the preferred content of the acid catalyst is preferably at least 0.05 part by mass, more preferably at least 0.1 part by mass, based on 100 parts by mass of all the alkoxysilane compounds used in the hydrolysis reaction. , Preferably 10 parts by mass or less, more preferably 5 parts by mass or less.
- the total amount of the alkoxysilane compound refers to an amount including all of the alkoxysilane compound, its hydrolyzate, and its condensate, and hereinafter the same.
- the weight average molecular weight (Mw) of the polysiloxane (A) used in the resin composition of the present invention is not particularly limited, but is preferably 1,000 or more in terms of polystyrene measured by gel permeation chromatography (GPC). More preferably, it is 2,000 or more. Further, it is preferably at most 100,000, more preferably at most 50,000. By setting Mw within the above range, good coating characteristics can be obtained, and the solubility in a developing solution at the time of pattern formation also becomes good.
- the content of the polysiloxane (A) is not particularly limited and can be arbitrarily selected depending on the desired film thickness and intended use, but is generally 5% by mass to 80% by mass in the resin composition. It is. Further, the content is preferably from 5% by mass to 50% by mass, more preferably from 20% by mass to 40% by mass in the solid content.
- Ion-exchanged water is preferable as the water used for the hydrolysis reaction.
- the amount of water can be arbitrarily selected, but is preferably used in the range of 1.0 to 4.0 mol per 1 mol of the alkoxysilane compound.
- the polysiloxane solution after hydrolysis and partial condensation does not contain the above catalyst, and the catalyst can be removed as necessary.
- water washing and / or treatment with an ion-exchange resin are preferred from the viewpoint of easy operation and removability.
- the water washing is a method of diluting a polysiloxane solution with an appropriate hydrophobic solvent, washing the resultant with water several times, and concentrating an organic layer obtained using an evaporator or the like.
- the treatment with an ion exchange resin is a method in which a polysiloxane solution is brought into contact with an appropriate ion exchange resin.
- the polysiloxane (A) used in the resin composition of the present invention is an organosilane compound derived from any of the structures of the above general formulas (1) to (3), and any one of the above general formulas (4) and (5). Hydrolyzing an organosilane compound derived from such a structure, and preferably an organosilane compound derived from any of the structures represented by the general formulas (9) to (11) in the presence of metal compound particles described below; When obtained by condensation of the hydrolyzate, the refractive index and hardness of the cured film are further improved.
- the metal compound particles By performing polymerization of the polysiloxane in the presence of the metal compound particles, a chemical bond (covalent bond) with the metal compound particles is generated in at least a part of the polysiloxane, and the metal compound particles are uniformly dispersed to preserve the coating liquid. It is considered that the stability and the uniformity of the cured film are improved. Further, the refractive index of the obtained cured film can be adjusted depending on the type of the metal compound particles. As the metal compound particles, those exemplified as metal compound particles described later can be used.
- the resin composition of the present invention contains (B) a solvent.
- the solvent used in the resin composition of the present invention is not particularly limited, but it is preferable to contain at least one aromatic hydrocarbon solvent having a hetero atom.
- Aromatic hydrocarbon solvents containing heteroatoms have high polarity but high solubility of organic compounds having a rigid skeleton such as naphthoquinonediazide.
- the liquid be a liquid at 23 ° C. and 1 atm. If the melting point is higher than this, it is necessary to heat the material during use, and it becomes difficult to treat it as a solvent.
- the boiling point of the solvent is preferably from 100 ° C to 300 ° C, more preferably from 120 ° C to 250 ° C.
- the boiling point is 100 ° C. or higher, the volatility of the solvent is appropriately suppressed, the leveling property during coating is improved, and a uniform coating film is easily formed.
- the boiling point is 300 ° C. or lower, the solvent hardly remains after the film is thermally cured, and the outgas of the cured film can be reduced.
- aromatic hydrocarbon solvent having a hetero atom examples include benzyl alcohol, 2-methylbenzyl alcohol, 3-methylbenzyl alcohol, 4-methylbenzyl alcohol, 4-isopropylbenzyl alcohol, 1-phenylethyl alcohol, 2-phenyl-2-propanol, 2-ethylbenzyl alcohol, 3-ethylbenzyl alcohol, 4-ethylbenzyl alcohol, anisole, 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, 1,4-dimethoxybenzene, phenyl Ether, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, dibenzyl ether, methyl benzoate, ethyl benzoate, and 1,4-bis (methoxymethyl) benzene.
- the content of these solvents is preferably from 10 to 50% by mass, more preferably from 20 to 40% by mass, based on all the solvents in the resin composition.
- the content is 50% by mass or less, the drying property is improved when the resin composition is applied and dried.
- the content is 10% by mass or more, the compatibility between the siloxane and the photosensitive agent is improved, and the coating property is improved.
- solvent (B) used in the resin composition of the present invention include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, and propylene glycol monopropyl.
- Ethers such as ether, propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether; ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propyl acetate, butyl Acetate, isobutyl acetate, 3-methoxybutyl acetate Acetates, such as acetate, 3-methyl-3-methoxybutyl acetate, methyl lactate, ethyl lactate, butyl lactate, ethyl acetoacetate, methyl acetoacetate, propyl acetoacetate, butyl acetoacetate, and benzyl acetoacetate; acetylacetone, methylpropyl Ketones such as ketone, methyl butyl ketone, methyl isobutyl
- the solvent include propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, and diacetone alcohol. , ⁇ -butyrolactone, ethyl lactate and the like. These may be used alone or in combination of two or more.
- the content of the total solvent in the resin composition of the present invention is preferably in the range of 100 parts by mass to 9900 parts by mass, more preferably 100 parts by mass to 5000 parts by mass, based on 100 parts by mass of the total alkoxysilane compound content. Range.
- the resin composition of the present invention preferably contains (C) a naphthoquinonediazide compound.
- the resin composition containing a naphthoquinonediazide compound forms a positive type in which exposed portions are removed by a developer.
- the naphthoquinonediazide compound used is not particularly limited, but is preferably a compound in which naphthoquinonediazidesulfonic acid is ester-bonded to a compound having a phenolic hydroxyl group, and the ortho position and the para position of the phenolic hydroxyl group of the compound are each independently.
- a compound that is either hydrogen or a substituent represented by the general formula (15) is used.
- R 17 , R 18 , and R 19 each independently represent any one of an alkyl group having 1 to 10 carbon atoms, a carboxyl group, a phenyl group, and a substituted phenyl group. Further, R 17 , R 18 and R 19 may form a ring.
- the alkyl group may be either unsubstituted or substituted, and can be selected according to the characteristics of the composition. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-hexyl, cyclohexyl, n-heptyl, and n-butyl.
- Examples include an octyl group, a trifluoromethyl group, and a 2-carboxyethyl group.
- Examples of the substituent on the phenyl group include a hydroxyl group and a methoxy group.
- Specific examples of the case where R 17 , R 18 , and R 19 form a ring include a cyclopentane ring, a cyclohexane ring, an adamantane ring, and a fluorene ring.
- these naphthoquinonediazide compounds can be synthesized by a known esterification reaction between a compound having a phenolic hydroxyl group and naphthoquinonediazidesulfonic acid chloride.
- Specific examples of the compound having a phenolic hydroxyl group include the following compounds (all manufactured by Honshu Chemical Industry Co., Ltd.).
- 4-naphthoquinonediazidesulfonic acid chloride or 5-naphthoquinonediazidesulfonic acid chloride can be used as naphthoquinonediazidesulfonic acid chloride as a raw material.
- the 4-naphthoquinonediazidosulfonic acid ester compound is suitable for i-line exposure because it has absorption in the i-line (wavelength 365 nm) region.
- the 5-naphthoquinonediazidosulfonic acid ester compound has absorption in a wide range of wavelengths, and thus is suitable for exposure to a wide range of wavelengths.
- a naphthoquinonediazide compound preferably used in the present invention includes a compound represented by the following general formula (16).
- R 20 represents hydrogen or an alkyl group selected from 1 to 8 carbon atoms.
- R 21 , R 22 , and R 23 each represent a hydrogen atom, an alkyl group selected from 1 to 8 carbon atoms, an alkoxyl group, a carboxyl group, or an ester group.
- Each of R 21 , R 22 and R 23 may be the same or different.
- Q represents either a 5-naphthoquinonediazidosulfonyl group or a hydrogen atom, and not all of Q is a hydrogen atom.
- b, c, d, ⁇ , and ⁇ represent an integer of 0 to 4.
- the addition amount of the naphthoquinonediazide compound is not particularly limited, but is preferably 1 to 30 parts by mass, more preferably 1 to 15 parts by mass, per 100 parts by mass of the resin (polysiloxane).
- the addition amount of the naphthoquinonediazide compound is less than 1 part by mass, the dissolution contrast between the exposed and unexposed portions is too low and does not exhibit practically sufficient photosensitivity.
- the amount is preferably 5 parts by mass or more.
- the addition amount of the naphthoquinonediazide compound is more than 30 parts by mass, whitening of the coating film occurs due to poor compatibility between the polysiloxane and the naphthoquinonediazide compound, or coloring due to decomposition of the quinonediazide compound which occurs during heat curing. Because it becomes remarkable, the colorless transparency of the cured film decreases. Further, in order to obtain a highly transparent film, the amount is preferably 15 parts by mass or less.
- the present invention preferably contains metal compound particles.
- the metal compound particles are not particularly limited, but preferably contain (D) silica particles from the viewpoint of adjusting the refractive index.
- (D) In the presence of silica particles and (B) a solvent, a silane compound derived from any of the structures of the above general formulas (1) to (3) and a structure of the above general formulas (4) and (5) From the viewpoint of compatibility, it is preferable to use a composite siloxane resin with silica particles (D) obtained by subjecting a derived silane compound to a condensation reaction after hydrolysis.
- the silica particles preferably have a number average particle diameter of 1 to 200 nm.
- the number average particle diameter is more preferably from 1 to 120 nm.
- the number average particle diameter is more preferably 30 to 100 nm. If it is 1 nm or more, the low refractive index property is sufficient, and if it is 200 nm or less, the reflection is sufficiently suppressed, and the hardness of the film is sufficiently high.
- the number average particle diameter of the silica particles should be measured by a gas adsorption method, a dynamic light scattering method, an X-ray small angle scattering method, a method of directly measuring the particle diameter by a transmission electron microscope or a scanning electron microscope, or the like. Can be.
- the number average particle diameter of the particles in the present invention refers to a value measured by a dynamic light scattering method.
- the silica particles (D) used in the present invention include silica particles having a porous and / or hollow inside and silica particles that are not porous and have no hollow inside.
- silica particles silica particles having a porous and / or hollow inside are preferred for lowering the refractive index of the coating film.
- Silica particles that are not porous and do not have hollows have a small refractive index reduction effect because the particles themselves have a refractive index of 1.45 to 1.5.
- silica particles having a porous and / or hollow interior have a large effect of lowering the refractive index because the particles themselves have a refractive index of 1.2 to 1.4. That is, silica particles having a porous and / or hollow inside are preferably used because they can impart excellent hardness and can impart low refractive index.
- Silica particles having a hollow inside refer to silica particles having a hollow portion surrounded by an outer shell. Further, the silica particles having a porous inside used in the present invention refers to silica particles having a large number of cavities on the surface or inside of the particles. Among these, in consideration of the hardness of the transparent coating, silica particles having hollows with high strength of the particles themselves are preferable.
- the silica particles themselves preferably have a refractive index of 1.2 to 1.4, more preferably 1.2 to 1.35.
- These silica particles (D) can be produced by the methods disclosed in Japanese Patent No. 3272111 and Japanese Patent Application Laid-Open No. 2001-233611. Examples of such (D) silica particles include, for example, those disclosed in JP-A-2001-233611 and those commercially available as disclosed in Japanese Patent No. 3272111.
- the refractive index of the silica particles can be measured by the following method.
- a mixed solution sample of (D) a matrix resin having a solid content concentration of 10% and a silica particle (D) prepared by adjusting the content of silica particles to 0% by mass, 20% by mass, 30% by mass, 40% by mass, and 50% by mass was prepared. Each of them was prepared and applied on a silicon wafer using a spin coater to a thickness of 0.3 to 1.0 ⁇ m, and then heated and dried on a hot plate at 200 ° C. for 5 minutes to form a coating film. Get.
- the refractive index at a wavelength of 633 nm is determined using, for example, an ellipsometer (manufactured by Otsuka Electronics Co., Ltd.), and the value can be determined by extrapolating the value of (D) 100% by mass of the silica particles.
- Introducing silica particles having a porous and / or hollow inside into the coating material can not only optimize the refractive index of the film obtained from the coating material but also increase the hardness of the film. preferable.
- the silica particles which are not porous and have no hollow are, for example, IPA-ST using 12 nm particle size isopropanol as a dispersant, MIBK-ST using 12 nm particle size methyl isobutyl ketone as a dispersant, particles IPA-ST-L using isopropanol having a diameter of 45 nm as a dispersing agent, IPA-ST-ZL using isopropanol having a particle diameter of 100 nm as a dispersing agent (trade name, manufactured by Nissan Chemical Industries, Ltd.), ⁇ having a particle diameter of 12 nm -Oscar 101 using butyrolactone as a dispersant, Oscar 105 using 60-nm-diameter ⁇ -butyrolactone as a dispersant, and Oscar 106 using 120-nm-diameter diacetone alcohol as a dispersant. Co., Ltd.).
- the presence or absence of the hollow can be confirmed by a particle cross
- Examples of commercially available (D) silica particles include organosilica sol “OSCAL” (manufactured by JGC Catalysts & Chemicals, Inc.), colloidal silica “Snowtex”, organosilica sol (manufactured by Nissan Chemical Industries, Ltd.), High-purity colloidal silica, high-purity organosol “Quartron” (Fuso Chemical Industry Co., Ltd.) and the like can be mentioned.
- organosilica sol “OSCAL” manufactured by JGC Catalysts & Chemicals, Inc.
- colloidal silica “Snowtex” manufactured by Nissan Chemical Industries, Ltd.
- High-purity colloidal silica high-purity organosol “Quartron” (Fuso Chemical Industry Co., Ltd.) and the like can be mentioned.
- a cured film having a low refractive index it is preferable to contain hollow silica particles.
- the presence or absence of the hollow can be confirmed by a particle cross-sectional image by a TEM (scanning electron microscope) photograph.
- the content of the silica particles is not particularly limited and may be an appropriate amount depending on the application, but is generally about 1 to 80% by mass of the total solids of the siloxane-based resin composition. .
- the resin composition of the present invention is obtained by mixing at least the (A) polysiloxane, (B) a solvent, and preferably (C) a naphthoquinonediazide compound. At this time, it may be diluted with an arbitrary solvent.
- the mixing temperature is not particularly limited, but is preferably in the range of 5 to 50 ° C. for simplicity of operation.
- the siloxane resin composition of the present invention may contain various curing agents for accelerating the curing of the resin composition or facilitating the curing.
- the curing agent include nitrogen-containing organic substances, silicone resin curing agents, various metal alcoholates, various metal chelate compounds, isocyanate compounds and polymers thereof, methylolated melamine derivatives, methylolated urea derivatives, and the like. Or two or more kinds.
- a metal chelate compound is preferably used in view of transparency of a coating film, stability of a curing agent, and the like.
- the metal chelate compound examples include a titanium chelate compound, a zirconium chelate compound, an aluminum chelate compound and a magnesium chelate compound. These metal chelate compounds can be easily obtained by reacting a metal alkoxide with a chelating agent.
- the chelating agent include ⁇ -diketones such as acetylacetone, benzoylacetone, and dibenzoylmethane; and ⁇ -keto acid esters such as ethyl acetoacetate and ethyl benzoylacetate.
- the metal chelate compound examples include ethyl acetoacetate aluminum diisopropylate, aluminum tris (ethyl acetoacetate), alkyl acetoacetate aluminum diisopropylate, aluminum monoacetyl acetate bis (ethyl acetoacetate), and aluminum tris ( Aluminum chelate compounds such as acetylacetonate), magnesium chelate compounds such as ethyl acetoacetate magnesium monoisopropylate, magnesium bis (ethyl acetoacetate), alkyl acetoacetate magnesium monosopropylate, and magnesium bis (acetylacetonate).
- the content of the curing agent is preferably 0.1% by mass to 10% by mass, more preferably 0.5% by mass to 6% by mass, based on the solid content in the siloxane resin composition.
- the resin composition of the present invention may contain a curing catalyst such as a thermal acid generator.
- a curing catalyst such as a thermal acid generator.
- the thermal acid generator include various onium salt compounds such as aromatic diazonium salts, sulfonium salts, diaryliodonium salts, triarylsulfonium salts, and triarylselenium salts, sulfonic acid esters, and halogen compounds.
- sulfonium salt 4-hydroxyphenyldimethylsulfonium triflate (prototype "W” manufactured by Sanshin Chemical Industry Co., Ltd.) and benzyl-4-hydroxyphenylmethylsulfonium triflate (prototype) “O” (manufactured by Sanshin Chemical Industry Co., Ltd.), 2-methylbenzyl-4-hydroxyphenylmethylsulfonium triflate (prototype “N” manufactured by Sanshin Chemical Industry Co., Ltd.), 4-methylbenzyl-4 -Hydroxyphenylmethylsulfonium triflate, 4-hydroxyphenylmethyl-1-naphthylmethylsulfonium triflate, 4-methoxycarbonyloxyphenyldimethylsulfonium triflate (prototype "J” Sansan Chemical Industry Co., Ltd.
- aromatic diazonium salt examples include chlorobenzenediazonium hexafluorophosphate, dimethylaminobenzenediazonium hexafluoroantimonate, naphthyldiazonium hexafluorophosphate, and dimethylaminonaphthyldiazonium tetrafluoroborate.
- diaryliodonium salt examples include diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluoroantimonate, diphenyliodonium hexafluorophosphate, diphenyliodonium triflate, 4,4′-di-t-butyl-diphenyliodonium triflate, 4,4'-di-t-butyl-diphenyliodonium tetrafluoroborate, 4,4'-di-t-butyl-diphenyliodonium hexafluorophosphate and the like.
- triarylsulfonium salt examples include triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, tri (p-chlorophenyl) sulfonium tetrafluoroborate, (P-chlorophenyl) sulfonium hexafluorophosphate, tri (p-chlorophenyl) sulfonium hexafluoroantimonate, 4-t-butyltriphenylsulfonium hexafluorophosphate, and the like.
- triarylselenium salts include triphenylselenium tetrafluoroborate, triphenylselenium hexafluorophosphate, triphenylselenium hexafluoroantimonate, di (chlorophenyl) phenylselenium tetrafluoroborate, and di (chlorophenyl) phenylselenium hexafluoro Phosphate, di (chlorophenyl) phenyl selenium hexafluoroantimonate and the like can be mentioned.
- sulfonic acid esters examples include benzoin tosylate, p-nitrobenzyl-9,10-ethoxyanthracene-2-sulfonate, 2-nitrobenzyl tosylate, 2,6-dinitrobenzyl tosylate, and 2,4-dinitrobenzyl tosylate And the like.
- halogen compound examples include 2-chloro-2-phenylacetophenone, 2,2 ', 4'-trichloroacetophenone, 2,4,6-tris (trichloromethyl) -s-triazine, and 2- (p-methoxystyryl)- 4,6-bis (trichloromethyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -S-triazine, 2- (4'-methoxy-1'-naphthyl) -4,6-bis (trichloromethyl) -s-triazine, bis-2- (4-chlorophenyl) -1,1,1-trichloroethane , Bis-1- (4-chlorophenyl) -2,2,2-trichloroethanol, bis-2- (4-methoxyphenyl)
- 5-norbornene-2,3-dicarboximidyl triflate (trade name “NDI-105” manufactured by Midori Kagaku Co., Ltd.), 5-norbornene-2,3-dicarboximidyl tosylate (trade name “NDI -101 "manufactured by Midori Kagaku Co., Ltd.), 4-methylphenylsulfonyloxyimino- ⁇ - (4-methoxyphenyl) acetonitrile (trade name” PAI-101 "manufactured by Midori Kagaku Co., Ltd.), trifluoromethylsulfonyloxyimino - ⁇ - (4-methoxyphenyl) acetonitrile (trade name “PAI-105” manufactured by Midori Kagaku Co., Ltd.), 9-camphorsulfonyloxyimino ⁇ -4-methoxyphenylacetonitrile (trade name “PAI-106”) Midori Chemical ( Co., Ltd.),
- the resin composition of the present invention may contain various surfactants such as various fluorine-based surfactants and silicone-based surfactants in order to improve flowability at the time of application.
- various surfactants such as various fluorine-based surfactants and silicone-based surfactants in order to improve flowability at the time of application.
- type of surfactant for example, “MegaFac (registered trademark)” F142D, F172, F173, F183, F430, F444, F445, F470, F475, F477, F553, F554, F555, F556, F559, F560, F563 (all manufactured by Dainippon Ink and Chemicals, Inc.), NBX-15, FTX-218, DFX-18 (Neos Corporation) Fluorinated surfactants such as LE-604, LE-605, LE-606, LE-607 (manufactured by Kyoeisha Chemical Co., Ltd.), BYK-333, BYK-301, BYK-331, B
- the resin composition of the present invention may contain, if necessary, a silane coupling agent, a crosslinking agent, a crosslinking accelerator, a sensitizer, a thermal radical generator, a dissolution accelerator, a dissolution inhibitor, a stabilizer, and an antifoaming agent. And the like.
- the cured film of the present invention is obtained by curing the resin composition of the present invention or the photosensitive resin composition which is the resin composition of the present invention.
- the photosensitive resin composition will be described in detail.
- One embodiment of the method for producing a cured film of the photosensitive resin composition preferably includes the following steps. (I) a step of applying a photosensitive resin composition on a substrate to form a coating film; (II) a step of exposing and developing the coating, and (III) a step of heating the developed coating. An example will be described below.
- the photosensitive resin composition is coated on the substrate by a known method such as spin coating or slit coating, and heated (prebaked) using a heating device such as a hot plate or an oven. Prebaking is preferably performed at a temperature in the range of 50 to 150 ° C. for 30 seconds to 30 minutes. The film thickness after prebaking is preferably 0.1 to 15 ⁇ m.
- an ultraviolet-visible exposure machine such as a stepper, a mirror projection mask aligner (MPA), or a parallel light mask aligner (PLA)
- MPA mirror projection mask aligner
- PLA parallel light mask aligner
- the (un) exposed area is dissolved and removed by development to obtain a negative or positive pattern.
- the resolution of the pattern is preferably 15 ⁇ m or less.
- a developing method it is preferable to immerse in a developing solution for 5 seconds to 10 minutes by a method such as shower, dip, or paddle.
- a known alkali developing solution can be used.
- inorganic alkalis such as alkali metal hydroxides, carbonates, phosphates, silicates and borates, 2-diethylaminoethanol
- examples include aqueous solutions of amines such as ethanolamine and diethanolamine, and quaternary ammonium salts such as tetramethylammonium hydroxide (TMAH) and choline.
- TMAH tetramethylammonium hydroxide
- dehydration and baking may be performed at a temperature in the range of 50 to 150 ° C. using a heating device such as a hot plate or an oven.
- the film is heated (soft bake) at a temperature of 50 to 300 ° C. for 30 seconds to 30 minutes using a heating device such as a hot plate or an oven if necessary, and then heated to 150 to 300 ° C. using a heating device such as a hot plate or an oven.
- a heating device such as a hot plate or an oven.
- the photosensitive resin composition from the viewpoint of productivity in the pattern formation, it is preferable that the sensitivity at the time of exposure is 1500 J / m 2 or less, more preferably 1000 J / m 2 or less.
- the sensitivity at the time of exposure is determined by the following method.
- the photosensitive resin composition is spin-coated on a silicon wafer at an arbitrary number of revolutions using a spin coater, and prebaked at 120 ° C. for 3 minutes using a hot plate to produce a prebaked film having a thickness of 1 ⁇ m.
- a cured film is prepared by curing at 220 ° C. for 5 minutes using a hot plate, and the minimum pattern dimension in sensitivity is determined as the post-curing resolution.
- FIG. 1 shows a specific example of the method for manufacturing a cured film according to the present embodiment.
- the resin composition of the present invention is applied on a substrate 1 to form a coating film 2. This is overheat-cured to obtain a cured film 3.
- FIG. 2 shows a specific example of the method for manufacturing a cured film according to the present embodiment.
- the steps up to the formation of the first coating film 2 are performed as described above.
- the coating film 2 is exposed to actinic rays 4 and exposed. This is cured by heating to obtain a cured film 3.
- FIG. 3 shows a specific example of the method for manufacturing a cured film according to the present embodiment.
- the steps up to the formation of the first coating film 2 are performed as described above.
- the coating film 2 is exposed to actinic light 4 via the mask 5 to be exposed.
- the pattern 6 is obtained by developing the exposed coating film.
- the pattern is irradiated with actinic rays 5 and cured by heating, whereby a cured film 3 is obtained.
- the cured film obtained by curing the fat composition of the present invention preferably has a light transmittance of 90% or more, more preferably 92% or more per 1 ⁇ m of film thickness at a wavelength of 400 nm.
- a high transmittance can be easily obtained, for example, by a photosensitive resin composition using a highly transparent polysiloxane as a resin component.
- the transmittance of the cured film per 1 ⁇ m of film thickness at a wavelength of 400 nm is determined by the following method.
- the photosensitive resin composition is spin-coated on a Tempax glass plate using a spin coater at an arbitrary rotation speed, and prebaked at 100 ° C. for 3 minutes using a hot plate.
- the composition is thermally cured at 220 ° C. for 5 minutes in the air using a hot plate to produce a cured film having a thickness of 1 ⁇ m.
- the ultraviolet-visible absorption spectrum of the obtained cured film is measured using MultiSpec-1500 manufactured by Shimadzu Corporation, and the transmittance at a wavelength of 400 nm is determined.
- the extinction coefficient and the film thickness of each target cured film at each wavelength can be measured by a spectroscopic ellipsometer FE5000 manufactured by Otsuka Electronics Co., Ltd., and can be obtained by the following equation.
- Transmittance exp ( ⁇ 4 ⁇ kt / ⁇ )
- k the extinction coefficient
- t the film thickness
- ⁇ the measurement wavelength
- the resin composition of the present invention and a cured film obtained by curing the resin composition are suitably used for a solid-state imaging device, an optical filter, an organic EL device, and a display device such as a liquid crystal display, an organic EL television, particularly a transparent liquid crystal television.
- a solid-state imaging device optical filter such as a backside illumination CMOS image sensor, a color mixing prevention wall, a transparent pixel, a flattening material for a display TFT substrate, a liquid crystal display, a color filter such as a see-through display, and the like.
- a protective film, a phase shifter, and an antireflection film can be used as a buffer coat of a semiconductor device, an interlayer insulating film, or various protective films.
- Apparatus JNM GX-270 manufactured by JEOL Ltd.
- Measurement method Gated decoupling method Measurement nuclear frequency: 53.6693 MHz ( 29 Si nucleus), spectrum width: 20000 Hz Pulse width: 12 ⁇ sec (45 ° pulse), pulse repetition time: 30.0 sec Solvent: acetone-d6, reference substance: tetramethylsilane Measurement temperature: room temperature, sample rotation speed: 0.0 Hz.
- the solid concentration of the polysiloxane solution was determined by the following method. 1.5 g of the polysiloxane solution was weighed into an aluminum cup and heated at 250 ° C. for 30 minutes using a hot plate to evaporate the liquid. The solid content remaining in the heated aluminum cup was weighed to determine the solid content concentration of the polysiloxane solution.
- HfTMS (Hf-1) was contacted with celite and filtered, and the filtrate was washed three times with 100 mL of water, dried by adding Na2SO4, and filtered, and the solvent was distilled off.
- the residue as a reaction product was distilled and produced using a Kugelrohr apparatus under the conditions of 140 ° C. to 190 ° C. and 200 Pa to obtain HfTMS (Hf-1) as a colorless liquid.
- the result of 1 H-NMR measurement of the obtained HfTMS (Hf-1) was as follows.
- HfTMS Hf-2
- Hf compound H-2
- Hf compound H-1
- the result of 1 H-NMR measurement of the obtained HfTMS (Hf-1) was as follows.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 20 mol% and 3 mol%, respectively.
- Synthesis Example 4 Synthesis of Polysiloxane (P-2)
- 112.22 g (0.551 mol) of MTMS, 66.97 g (0.037 mol) of HfTMS (Hf-1), and TES were prepared.
- 185.62 g of PGMEA were charged, and an aqueous phosphoric acid solution obtained by dissolving 1.01 g of phosphoric acid (0.50% by mass based on charged monomers) in 61.30 g of water was added.
- a siloxane (P-2) was obtained.
- the solid content concentration of the obtained polysiloxane (P-2) was 42.8% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 15 mol% and 10 mol%, respectively.
- the molar amount in the siloxane was 15 mol% and 50 mol%, respectively.
- Synthesis Example 6 Synthesis of Polysiloxane (P-4)
- 31.16 g (0.184 mol) of MTMS, 55.79 g (0.037 mol) of HfTMS (Hf-1), and TES were prepared.
- 188.34 g of PGMEA were charged, and an aqueous solution of phosphoric acid in which 1.01 g of phosphoric acid (0.50% by mass with respect to the charged monomers) was dissolved in 59.31 g of water was added.
- a siloxane (P-4) was obtained.
- the solid concentration of the obtained polysiloxane (P-4) was 42.5% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 15 mol% and 60 mol%, respectively.
- Synthesis Example 7 Synthesis of Polysiloxane (P-5)
- 63.63 g (0.137 mol) of CFTMS, 196.49 g of PGMEA were charged, and 1.00 g of phosphoric acid was added to 53.35 g of water (0.50 mass% based on the charged monomer).
- the dissolved phosphoric acid aqueous solution was added to obtain a polysiloxane (P-5).
- the solid concentration of the obtained polysiloxane (P-5) was 43.7% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5) The molar amount in the siloxane was 15 mol% and 5 mol%, respectively.
- Synthesis Example 8 Synthesis of Polysiloxane (P-6)
- 62.52 (0.137 mol) of CFTMS, 196.59 g of PGMEA were charged, and 1.00 g of phosphoric acid (0.50% by mass based on charged monomers) was added to 53.28 g of water.
- the dissolved phosphoric acid aqueous solution was added to obtain a polysiloxane (P-6).
- the solid concentration of the obtained polysiloxane (P-6) was 42.9% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 15 mol% and 10 mol%, respectively.
- Synthesis Example 9 Synthesis of Polysiloxane (P-7)
- MTMS was 46.14 g (0.257 mol)
- HfTMS (Hf-1) was 59.01 g (0.037 mol)
- TES was 30.24 g (0.072 mol)
- 63.38 (0.137 mol) of CFTMS 197.97 g of PGMEA were charged
- 0.99 g of phosphoric acid was added to 52.27 g of water (0.50 mass% based on the charged monomer).
- the dissolved phosphoric acid aqueous solution was added to obtain a polysiloxane (P-7).
- the solid concentration of the obtained polysiloxane (P-7) was 43.1% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 15 mol% and 20 mol%, respectively.
- Synthesis Example 10 Synthesis of Polysiloxane (P-8) In the same procedure as in Synthesis Example 1, 30.40 g (0.184 mol) of MTMS, 54.42 g (0.037 mol) of HfTMS (Hf-1), and TES were synthesized. 55.78 g (0.144 mol), 58.45 (0.137 mol) of CFTMS, 196.94 g of PGMEA were charged, and 1.00 g of phosphoric acid (0.50% by mass based on charged monomers) was added to 53.02 g of water. The dissolved phosphoric acid aqueous solution was added to obtain a polysiloxane (P-8).
- the solid concentration of the obtained polysiloxane (P-8) was 43.2% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5) The molar amount in the siloxane was 15 mol% and 30 mol%, respectively.
- the molar amount in the siloxane was 15 mol% and 50 mol%, respectively.
- Synthesis Example 12 Synthesis of Polysiloxane (P-10) In the same procedure as in Synthesis Example 1, 54.02 g (0.294 mol) of MTMS, 40.30 g (0.025 mol) of HfTMS (Hf-1), and TES were synthesized. 41.31 g (0.096 mol), 64.92 (0.137 mol) of CFTMS, 191.35 g of PGMEA were charged, and 1.00 g of phosphoric acid (0.50% by mass based on charged monomers) was added to 57.11 g of water. The dissolved phosphoric acid aqueous solution was added to obtain a polysiloxane (P-10).
- the solid content of the obtained polysiloxane (P-10) was 43.1% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5) The molar amount in the siloxane was 10 mol% and 20 mol%, respectively.
- Synthesis Example 13 Synthesis of Polysiloxane (P-11)
- 35.26 g (0.220 mol) of MTMS, 70.13 g (0.049 mol) of HfTMS (Hf-1), and TES 35.95 g (0.096 mol) of CFTMS, 201.48 g of PGMEA were charged, and 0.99 g of phosphoric acid was added to 49.70 g of water (0.50% by mass based on charged monomers).
- the dissolved phosphoric acid aqueous solution was added to obtain a polysiloxane (P-11).
- the solid concentration of the obtained polysiloxane (P-11) was 43.4% by mass.
- the molar amount in the siloxane was 20 mol% and 20 mol%, respectively.
- Synthesis Example 14 Synthesis of Polysiloxane (P-12)
- MTMS was 20.80 g (0.147 mol)
- HfTMS (Hf-1) was 93.11 g (0.074 mol)
- TES was 31.82 g (0.096 mol)
- 50.00 (0.137 mol) of CFTMS 209.29 g of PGMEA were charged, and 0.98 g of phosphoric acid (43.99 g of water) was added to 43.99 g of water.
- the dissolved phosphoric acid aqueous solution was added to obtain a polysiloxane (P-12).
- the solid content concentration of the obtained polysiloxane (P-12) was 43.0% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 30 mol% and 20 mol%, respectively.
- Synthesis Example 15 Synthesis of Polysiloxane (P-13) In a 500-ml three-necked flask, 109.25 g (0.565 mol) of MTMS, 84.67 g (0.049 mol) of HfTMS (Hf-2), and 6.51 g of TES ( 0.014 mol), 191.75 g of PGMEA were charged, and an aqueous phosphoric acid solution obtained by dissolving 1.00 g of phosphoric acid (0.50% by mass based on the charged monomers) in 56.82 g of water while stirring at room temperature was taken for 30 minutes. Was added. Thereafter, the flask was immersed in a 70 ° C.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 20 mol% and 3 mol%, respectively.
- Synthesis Example 16 Synthesis of Polysiloxane (R-1)
- HfTMS Hf-1
- PGMEA phosphorus-containing compound
- An aqueous solution of phosphoric acid in which 0.94 g of acid (0.50% by mass based on the charged monomer) was dissolved was added to obtain a polysiloxane (R-1).
- the solid concentration of the obtained polysiloxane (R-1) was 43.2% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 100 mol% and 0 mol%, respectively.
- Synthesis Example 17 Synthesis of Polysiloxane (R-2)
- 41.54 g (0.330 mol) of MTMS, 151.49 g (0.135 mol) of HfTMS (Hf-1), and PGMEA were prepared.
- the solid concentration of the obtained polysiloxane (R-2) was 43.5% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 55 mol% and 0 mol%, respectively.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 0 mol% and 0 mol%, respectively.
- Synthesis Example 19 Synthesis of Polysiloxane (R-4)
- 73.11 g (0.330 mol) of MTMS, 130.10 g (0.277 mol) of PhTMS, and 181.36 g of PGMEA were charged.
- the solid concentration of the obtained polysiloxane (R-4) was 42.8% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 0 mol% and 0 mol%, respectively.
- Synthesis Example 20 Synthesis of Polysiloxane (R-5)
- 120.70 g (0.111 mol) of HfTMS, 71.98 g (0.277 mol) of PhTMS, and 220.71 g of PGMEA were charged.
- An aqueous phosphoric acid solution obtained by dissolving 0.97 g of phosphoric acid (0.50% by mass based on the charged monomers) in 35.64 g of water was added to obtain a polysiloxane (R-5).
- the solid content of the obtained polysiloxane (R-5) was 43.2% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 45 mol% and 0 mol%, respectively.
- Synthesis Example 21 Synthesis of Polysiloxane (R-6)
- 66.32 g (0.049 mol) of HfTMS, 129.44 g (0.403 mol) of PhTMS, and 209.20 g of PGMEA were charged.
- An aqueous phosphoric acid solution obtained by dissolving 0.98 g of phosphoric acid (0.50% by mass based on charged monomers) in 44.06 g of water was added to obtain a polysiloxane (R-6).
- the solid concentration of the obtained polysiloxane (R-6) was 43.2% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 20 mol% and 0 mol%, respectively.
- Table 1 shows the charged amounts of the alkoxysilanes, which are the raw materials for the polysiloxane (A) obtained in Synthesis Examples 1 to 18.
- Synthesis Example 22 Synthesis of Polysiloxane (R-7) In the same procedure as in Synthesis Example 1, 15.46 g (0.011 mol) of MTMS, 19.27 g (0.088 mol) of CFTMS, and 10.51 g (0. 0.050 mol), 40.01 g of PGMEA, and an aqueous solution of phosphoric acid in which 0.23 g of phosphoric acid (0.50% by mass based on the charged monomer) was dissolved in 14.53 g of water, and polysiloxane (R-7) was added. ) Got. The solid concentration of the obtained polysiloxane (R-6) was 43.2% by mass.
- the (A) poly (A) having a structure represented by any of the general formulas (1) to (3) and a structure represented by any of the general formulas (4) or (5)
- the molar amount in the siloxane was 0 mol% and 20 mol%, respectively.
- Table 1 shows the charged amounts of the alkoxysilanes, which are the raw materials for the polysiloxane (A) obtained in Synthesis Examples 1 to 22.
- Solvent Substitution Example 1 Solvent Substitution of "Surria” 4110 As metal oxide particles, the solvent of "Surria” 4110 (trade name, manufactured by JGC Catalysts & Chemicals, Inc.) was replaced with PGMEA from isopropanol. A 500 ml eggplant flask was charged with 100 g of Isopropanol sol (solid content concentration: 20%) of Sluria 4110 and 80 g of PGMEA, and the pressure was reduced at 30 ° C. for 30 minutes using an evaporator to remove IPA. The PGMEA solution of the resulting Sluria 4110 was obtained. The solid concentration of D-1 was measured and found to be 20.1%.
- the thickness of the obtained cured film was measured (1) and the thickness was determined as a thickness t1. Subsequently, the cured film was immersed in acetone for 5 minutes, and then heated at 100 ° C. for 1 minute using a hot plate (HP-1SA manufactured by AS ONE Corporation). After the heating, the thickness of the cured film was measured by Surfcom to determine the thickness t2. The film thickness change rate X before and after acetone immersion was calculated by the following formula, and the chemical resistance was evaluated. The evaluation criteria are A to E below.
- Film thickness change rate X (%) (t1 ⁇ t2) / t1 ⁇ 100
- the minimum pattern dimension x is x ⁇ 15 ⁇ m
- B The minimum pattern dimension x is 15 ⁇ m ⁇ x ⁇ 50 ⁇ m
- C The minimum pattern dimension x is 50 ⁇ m ⁇ x ⁇ 100 ⁇ m
- D The minimum pattern dimension x is 100 ⁇ m ⁇ x.
- Example 1 The mixture was prepared according to the ratio of the resin composition (I) in Table 2, mixed and stirred under a yellow light to form a uniform solution, and then filtered through a 0.20 ⁇ m filter to prepare Composition 1.
- spin coating is performed on a 4-inch silicon wafer using a spin coater (1H-360S manufactured by Mikasa Corporation), and then using a hot plate (SCW-636 manufactured by Dainippon Screen Mfg. Co., Ltd.). Heating at 120 ° C. for 3 minutes produced a pre-baked film having a thickness of 1.0 ⁇ m. Thereafter, the pre-baked film was cured at 230 ° C. for 5 minutes using a hot plate to form a cured film 1.
- Example 19 The mixture was prepared at the ratio of the resin composition (I) in Table 4, mixed and stirred under a yellow light to form a uniform solution, and then filtered through a 0.20 ⁇ m filter to prepare a composition 25.
- a 4-inch silicon wafer and a glass substrate were spin-coated using a spin coater (1H-360S, manufactured by Mikasa Co., Ltd.), and then heated on a hot plate (SCW-, manufactured by Dainippon Screen Mfg. Co., Ltd.). 636) and heated at 120 ° C. for 3 minutes to produce a pre-baked film, and (1) film thickness measurement was performed.
- the prebaked film was shower-developed with a 2.38% by mass TMAH aqueous solution for 30 seconds using an automatic developing device (AD-2000 manufactured by Takizawa Sangyo Co., Ltd.), rinsed with water for 30 seconds, and then on the wafer and the glass substrate.
- the obtained prebaked film is exposed by using an i-line stepper (i9C manufactured by Nikon Corporation) at intervals of 50 msec from 100 msec to 1000 msec, and then developed and cured in the same manner as described above. I got
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Abstract
La présente invention concerne une composition de résine qui présente un faible indice de réfraction, est excellente en termes de résistance à la chaleur, résistance chimique et applicabilité, et présente une excellente aptitude à la formation de motifs. La composition de résine comprend (A) un polysiloxane et (B) un solvant, et est caractérisée en ce que le polysiloxane (A) comprend une structure représentée par l'une quelconque des formules générales spécifiques (1) à (3) et une structure représentée par l'une quelconque des formules générales spécifiques (4) et (5).
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CN201980040304.1A CN112368336A (zh) | 2018-08-31 | 2019-08-22 | 树脂组合物、其固化膜 |
KR1020217000310A KR20210052431A (ko) | 2018-08-31 | 2019-08-22 | 수지 조성물, 그의 경화막 |
JP2019549505A JP7327163B2 (ja) | 2018-08-31 | 2019-08-22 | 樹脂組成物、その硬化膜 |
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JP (1) | JP7327163B2 (fr) |
KR (1) | KR20210052431A (fr) |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2021186994A1 (fr) * | 2020-03-16 | 2021-09-23 | セントラル硝子株式会社 | Composition, solution de précurseur de composition, procédé de production de composition, substrat et procédé de production pour substrat à motifs |
WO2022131278A1 (fr) * | 2020-12-15 | 2022-06-23 | セントラル硝子株式会社 | Fluide de revêtement pour élément optique, polymère, film durci, fluide de revêtement photosensible, film durci à motifs, élément optique, élément d'imagerie à semi-conducteur, dispositif d'affichage, composé de polysiloxane, stabilisant destiné à être utilisé dans un fluide de revêtement, procédé de production de film durci, procédé de production de film durci à motifs et procédé de production de polymère |
CN116107163A (zh) * | 2022-12-28 | 2023-05-12 | 上海玟昕科技有限公司 | 一种含纳米粒子的正性光刻胶组合物 |
WO2023171487A1 (fr) * | 2022-03-07 | 2023-09-14 | 東レ株式会社 | Composition de résine photosensible, article durci, dispositif d'affichage et procédé de production de dispositif d'affichage |
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JP2006085129A (ja) * | 2004-08-19 | 2006-03-30 | Shin Etsu Chem Co Ltd | レジスト組成物並びにこれを用いたパターン形成方法 |
WO2014112584A1 (fr) * | 2013-01-21 | 2014-07-24 | セントラル硝子株式会社 | Composé silicium contenant des groupes hexafluoroisopropanol, son procédé de production, et composé polymère obtenu par polymérisation de celui-ci |
JP2015129908A (ja) * | 2013-11-01 | 2015-07-16 | セントラル硝子株式会社 | ポジ型感光性樹脂組成物、それを用いた膜の製造方法および電子部品 |
WO2019167771A1 (fr) * | 2018-02-28 | 2019-09-06 | セントラル硝子株式会社 | Composition pour formation de couche à teneur en silicium, et procédé de fabrication de substrat avec motif mettant en œuvre cette composition |
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WO2021186994A1 (fr) * | 2020-03-16 | 2021-09-23 | セントラル硝子株式会社 | Composition, solution de précurseur de composition, procédé de production de composition, substrat et procédé de production pour substrat à motifs |
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WO2022131278A1 (fr) * | 2020-12-15 | 2022-06-23 | セントラル硝子株式会社 | Fluide de revêtement pour élément optique, polymère, film durci, fluide de revêtement photosensible, film durci à motifs, élément optique, élément d'imagerie à semi-conducteur, dispositif d'affichage, composé de polysiloxane, stabilisant destiné à être utilisé dans un fluide de revêtement, procédé de production de film durci, procédé de production de film durci à motifs et procédé de production de polymère |
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CN116107163A (zh) * | 2022-12-28 | 2023-05-12 | 上海玟昕科技有限公司 | 一种含纳米粒子的正性光刻胶组合物 |
Also Published As
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KR20210052431A (ko) | 2021-05-10 |
TW202020024A (zh) | 2020-06-01 |
JPWO2020045214A1 (ja) | 2021-08-10 |
JP7327163B2 (ja) | 2023-08-16 |
CN112368336A (zh) | 2021-02-12 |
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