TW201632535A - 含氟的矽化合物與其製造方法、及含氟的矽樹脂之製造方法 - Google Patents
含氟的矽化合物與其製造方法、及含氟的矽樹脂之製造方法 Download PDFInfo
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- TW201632535A TW201632535A TW105103210A TW105103210A TW201632535A TW 201632535 A TW201632535 A TW 201632535A TW 105103210 A TW105103210 A TW 105103210A TW 105103210 A TW105103210 A TW 105103210A TW 201632535 A TW201632535 A TW 201632535A
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- Prior art keywords
- fluorine
- decane
- group
- acid
- ruthenium
- Prior art date
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- 239000011737 fluorine Substances 0.000 title claims abstract description 104
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- 229910052710 silicon Inorganic materials 0.000 title abstract 3
- 239000010703 silicon Substances 0.000 title abstract 3
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- NEVGLHITLLFEDP-UHFFFAOYSA-N [Ru].C(CC(=O)C)(=O)OCC(OCCC)OCCC Chemical compound [Ru].C(CC(=O)C)(=O)OCC(OCCC)OCCC NEVGLHITLLFEDP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- LIQDVINWFSWENU-UHFFFAOYSA-K aluminum;prop-2-enoate Chemical compound [Al+3].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C LIQDVINWFSWENU-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 125000001204 arachidyl 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])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
- 229910000413 arsenic oxide Inorganic materials 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- DJHZYHWLGNJISM-FDGPNNRMSA-L barium(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ba+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O DJHZYHWLGNJISM-FDGPNNRMSA-L 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- NIOLTQNBOYMEQK-UHFFFAOYSA-N butan-1-olate;zirconium(2+) Chemical compound [Zr+2].CCCC[O-].CCCC[O-] NIOLTQNBOYMEQK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- MRWDOMBCUHOHAE-UHFFFAOYSA-K cerium(3+);propanoate Chemical compound [Ce+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O MRWDOMBCUHOHAE-UHFFFAOYSA-K 0.000 description 1
- VGBWDOLBWVJTRZ-UHFFFAOYSA-K cerium(3+);triacetate Chemical compound [Ce+3].CC([O-])=O.CC([O-])=O.CC([O-])=O VGBWDOLBWVJTRZ-UHFFFAOYSA-K 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- QIESBVQBFFBEJV-UHFFFAOYSA-N chloro hypochlorite;tin Chemical compound [Sn].ClOCl QIESBVQBFFBEJV-UHFFFAOYSA-N 0.000 description 1
- XFVGXQSSXWIWIO-UHFFFAOYSA-N chloro hypochlorite;titanium Chemical compound [Ti].ClOCl XFVGXQSSXWIWIO-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- TWXWPPKDQOWNSX-UHFFFAOYSA-N dicyclohexylmethanone Chemical compound C1CCCCC1C(=O)C1CCCCC1 TWXWPPKDQOWNSX-UHFFFAOYSA-N 0.000 description 1
- GSPKZYJPUDYKPI-UHFFFAOYSA-N diethoxy sulfate Chemical compound CCOOS(=O)(=O)OOCC GSPKZYJPUDYKPI-UHFFFAOYSA-N 0.000 description 1
- HJALNAJFKFMKSG-UHFFFAOYSA-N diethoxy(oxo)tin Chemical compound CCO[Sn](=O)OCC HJALNAJFKFMKSG-UHFFFAOYSA-N 0.000 description 1
- QAIDPMSYQQBQTK-UHFFFAOYSA-N diethylgallium Chemical compound CC[Ga]CC QAIDPMSYQQBQTK-UHFFFAOYSA-N 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical compound OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- HIWDBXCAECYPGA-UHFFFAOYSA-N ethoxygallium Chemical compound CCO[Ga] HIWDBXCAECYPGA-UHFFFAOYSA-N 0.000 description 1
- VQNGANSRVZMYKT-UHFFFAOYSA-N ethoxyhydrazine Chemical compound CCONN VQNGANSRVZMYKT-UHFFFAOYSA-N 0.000 description 1
- IOTFKOAAMYQOBJ-UHFFFAOYSA-N ethyl acetate;2-methoxyethanol Chemical compound COCCO.CCOC(C)=O IOTFKOAAMYQOBJ-UHFFFAOYSA-N 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- ALPJHXLZJQMRLE-UHFFFAOYSA-N hexaaluminum oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3] ALPJHXLZJQMRLE-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 description 1
- GSCGQEWSUMGSEY-UHFFFAOYSA-N methoxyhydrazine Chemical compound CONN GSCGQEWSUMGSEY-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Chemical group 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical group [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- WHSXGLZHSWSLPF-UHFFFAOYSA-N oxygen(2-) phenylaluminum(2+) Chemical compound [O-2].[Al+2]C1=CC=CC=C1 WHSXGLZHSWSLPF-UHFFFAOYSA-N 0.000 description 1
- AZCUJQOIQYJWQJ-UHFFFAOYSA-N oxygen(2-) titanium(4+) trihydrate Chemical compound [O-2].[O-2].[Ti+4].O.O.O AZCUJQOIQYJWQJ-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CCTFOFUMSKSGRK-UHFFFAOYSA-N propan-2-olate;tin(4+) Chemical compound [Sn+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] CCTFOFUMSKSGRK-UHFFFAOYSA-N 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- PYKSLEHEVAWOTJ-UHFFFAOYSA-N tetrabutoxystannane Chemical compound CCCCO[Sn](OCCCC)(OCCCC)OCCCC PYKSLEHEVAWOTJ-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/08—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing boron
-
- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Materials For Photolithography (AREA)
Abstract
本發明提供作為半導體元件製造步驟之微細加工使用之含矽中間膜形成用組成物、及含矽之光阻組成物之原料等為有用且保存安定性良好之含氟的矽化合物。 下列通式(1)表示之含氟的矽化合物, 【化1】□式中,R1
各自獨立地為碳數1~6之烴基,R2
各自獨立地為氫原子或碳數1~6之烴基。n為符合0≦n≦2之整數。
Description
本發明係關於新的含氟的矽化合物、其製造方法、及使用其之含氟的矽樹脂之製造方法。
水解性的含氟的矽化合物在利用其導入調整縮合樹脂之各種特性時有用。有人提出使用在例如於半導體元件等製造步驟之微細加工使用之多層光阻法之中間層之含矽膜形成用組成物、或含矽之光阻組成物(專利文獻1、2)。
專利文獻2提出:下式(6)表示之1,1,1-三氟-5-(三乙氧基矽基)-2-(三氟甲基)-2-戊醇作為特別有用的水解性的含氟的矽化合物。但是前述化合物有保存安定性差的重大缺點,不適合實用,需要替代前述化合物且作為縮合樹脂之原料和前述化合物有同等機能之含氟的矽化合物。 【化1】[先前技術文獻] [專利文獻]
[專利文獻1] 日本特開2012-53253號公報 [專利文獻2] 日本專利公報第5178858號
[發明欲解決之課題] 本發明有鑑於上述情事,目的為提供作為在半導體元件製造步驟之微細加工使用之含矽中間膜形成用組成物、及含矽之光阻組成物之原料等為有用且保存安定性良好的含氟的矽化合物。 [解決課題之方式]
為了解決上述課題,本發明提供下列通式(1)表示之含氟的矽化合物。 【化2】(式中,R1
各自獨立地為碳數1~6之烴基,R2
各自獨立地為氫原子或碳數1~6之烴基。n為符合0≦n≦2之整數。)
若為如此的化合物,可成為作為半導體元件製造步驟之微細加工使用之含矽中間膜形成用組成物、及含矽之光阻組成物之原料等有用且保存安定性良好的含氟的矽化合物。
此時前述含氟的矽化合物宜成為含矽中間膜形成用組成物或含矽之光阻組成物所含之樹脂之製造原料較佳。
本發明之含氟的矽化合物易大量製造,保存安定性良好,故適合作為含矽中間膜形成用組成物、含矽之光阻組成物所含之樹脂之製造原料。
又,本發明提供前述含氟的矽化合物之製造方法,係製造使下列通式(2)表示之含氟的矽化合物進行分子內縮合。 【化3】(式中,R1
、R2
、及n同上述。)
本發明之含氟的矽化合物例如可依如下方法製造。
又,本發明提供前述含氟的矽化合物之製造方法,係使下式(3)表示之氟含有化合物與下列通式(4)表示之矽化合物反應。 【化4】(式中,R1
、R2
、及n同上述。)
本發明之含氟的矽化合物例如可依如下方法製造。
再者,本發明提供一種含氟的矽樹脂之製造方法,係使選自下列通式(5-1)表示之水解性矽化合物及下列通式(5-2)表示之反應性化合物構成之群組中之1種以上之化合物、與前述含氟的矽化合物之1種以上進行水解縮合。 R3 m1
Si(OR4
)(4-m1)
(5-1) U(OR5
)m2
(OR6
)m3
(O)m4/2
(5-2) (式中,R3
各自獨立地為氫原子或碳數1~30之1價有機基。R4
各自獨立地為碳數1~6之烴基,m1為符合0≦m1≦3之整數。R5
及R6
各自獨立地為氫原子或碳數1~30之有機基。U為不包括碳與矽之周期表之III族、IV族、及V族中任一元素。m2+m3+m4由U之種類決定的價數,m2、m3、及m4各為0以上之整數。)
若為如此的製造方法,可使用本發明之含氟的矽化合物和習知法同樣地輕易製造含氟的矽樹脂。 [發明之效果]
若為本發明之含氟的矽化合物,有用於作為半導體元件製造步驟之微細加工使用之含矽中間膜形成用組成物、及含矽之光阻組成物之原料等,且大量製造容易,且保存安定性良好,故工業利用價値非常高。又,本發明之含氟的矽化合物可因應化合物結構以最適方法製造。 再者,依本發明之含氟的矽樹脂之製造方法,能使用本發明之含氟的矽化合物和習知法同樣地輕易製造含氟的矽樹脂。
如上,對於作為半導體元件製造步驟之微細加工使用之含矽中間膜形成用組成物、及含矽之光阻組成物之原料等有用且保存安定性良好之含氟的矽化合物有所需求。
本案發明人等對於和上述1,1,1-三氟-5-(三乙氧基矽基)-2-(三氟甲基)-2-戊醇有同等機能且保存安定性良好之水解性含氟的矽化合物努力研究。結果找到下列通式(1)表示之含氟的矽化合物,並開發出其工業化製造方法,乃完成本發明。
亦即本發明提供下列通式(1)表示之含氟的矽化合物。 【化5】(式中,R1
各自獨立地為碳數1~6之烴基,R2
各自獨立地為氫原子或碳數1~6之烴基。n為符合0≦n≦2之整數。)
以下針對本發明詳細説明,但本發明不限於此等。 又本發明中,Me代表甲基、Et代表乙基、Pr代表丙基、i
Pr代表異丙基、Ph代表苯基。
[含氟的矽化合物] 本發明之含氟的矽化合物為下列通式(1)表示之含氟的矽化合物。 【化6】(式中,R1
各自獨立地為碳數1~6之烴基,R2
各自獨立地為氫原子或碳數1~6之烴基。n為符合0≦n≦2之整數。)
通式(1)中,R1
各自獨立地為碳數1~6之烴基,R2
各自獨立地為氫原子或碳數1~6之烴基。R1
具體而言可列舉甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、新戊基、環戊基、己基、環己基、苯基,R2
具體而言可列舉氫原子、甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、新戊基、環戊基、己基、環己基、苯基,但不限定於此等。R1
宜為甲基、乙基、丙基、異丙基尤佳。R2
宜為甲基、乙基、苯基尤佳。n為符合0≦n≦2之整數,尤其1或2為較佳。
本發明之含氟的矽化合物更具體而言為下式表示之化合物尤佳但不限定於此等。 【化7】
在此,前述保存安定性差之習知之含氟的矽化合物1,1,1-三氟-5-(三乙氧基矽基)-2-(三氟甲基)-2-戊醇(6),一般係利用水解縮合製成樹脂化而供實用。其水解縮合之反應如下列反應式所示,係經過水解所得之中間產物(7)獲得縮合製得之產物(8)。 【化8】
另一方面,本發明之含氟的矽化合物(1)也可利用水解縮合製成樹脂。其情形之反應如下列反應式所示,利用水解獲得之中間產物(7’)獲得縮合製得之產物(8’)。 【化9】(式中,R1
、R2
、及n同上述。)
如上,本發明之含氟的矽化合物(1)是和習知之1,1,1-三氟-5-(三乙氧基矽基)-2-(三氟甲基)-2-戊醇(6)不同的新化合物,比起以往保存安定性較良好,經水解縮合製成樹脂後,和使用習知之1,1,1-三氟-5-(三乙氧基矽基)-2-(三氟甲基)-2-戊醇(6)製造之樹脂有同樣結構,發揮同等性能。
[含氟的矽化合物之製造方法] 本發明之含氟的矽化合物可因應化合物之結構選用最適方法製造。具體而言,可列舉:(a)利用有醇性羥基之含氟的矽化合物之分子內縮合之製造方法(以下稱(a)法)、(b)利用1,1,1-三氟-2-(三氟甲基)-4-戊烯-2-醇與烷氧基氫矽烷化合物之反應之製造方法(以下稱(b)法),但不限於該等方法。以下詳述。
(a)法更具體而言係使下列通式(2)表示之含氟的矽化合物進行分子內縮合。 【化10】(式中,R1
、R2
、及n同上述。)
如下列反應式所示,藉由使通式(2)表示之含氟的矽化合物進行分子內縮合,可獲得本發明之含氟的矽化合物。 【化11】(式中,R1
、R2
、及n同上述。)
成為原料之含氟的矽化合物(2)可利用例如日本特開2004-295104號公報記載之製造方法取得。上述分子內縮合反應係例如無觸媒或觸媒存在下,於溶劑中或無溶劑中,將含氟的矽化合物(2)進行加熱或減壓以進行。
上述分子內縮合反應中,為了提高反應速度,可添加酸觸媒、鹼觸媒等。酸觸媒,可以從例如:硫酸、鹽酸、磷酸、過氯酸等無機酸類、三氟化硼、三氟化硼二乙醚錯合物、二丁基氧化錫、氯化鋁、氯化鋅、四氯鈦、四甲氧基鈦等路易士酸類、甲烷磺酸、對甲苯磺酸等磺酸類、硫酸氫鉀、氯化鈣、氯化鎂、對甲苯磺酸吡啶等鹽類、草酸、三氟乙酸等羧酸類、陽離子交換樹脂等酸性樹脂類之中依反應條件選擇而單獨使用或混用。酸觸媒之使用量相對於含氟的矽化合物(2)1莫耳,較佳為0~10莫耳,尤其0~5莫耳較理想。
鹼觸媒可以從例如:吡啶、三乙胺、二異丙基乙胺、4-二甲胺基吡啶、咪唑等胺類、甲醇鈉、乙醇鈉、第三丁醇鉀等金屬烷氧化物類、碳酸鈉、碳酸鉀、碳酸銫等碳酸鹽類、氫氧化鈉、氫氧化鉀、四甲基氫氧化銨等氫氧化物類、氫化鈉、氫化鉀等金屬氫化物類、丁基鋰、乙基溴化鎂等有機金屬類、二異丙基胺鋰等金屬氨化物類之中依反應條件選擇並單獨使用或混用。鹼觸媒之使用量相對於含氟的矽化合物(2)1莫耳,較佳為0~10莫耳,尤其0~5莫耳較理想。
反應於溶劑中進行時之反應溶劑,可以從己烷、庚烷、苯、甲苯、二甲苯等烴系溶劑、二乙醚、二丁醚、四氫呋喃、1,4-二烷、二甘二甲醚等醚系溶劑、二氯甲烷、氯仿、1,2-二氯乙烯等氯系溶劑、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、二甲基亞碸、N-甲基吡咯烷酮等非質子性極性溶劑、乙酸乙酯、乙酸丁酯等酯系溶劑、丙酮、2-丁酮等酮系溶劑、乙腈等腈系溶劑之中依反應條件選擇並單獨使用或混用。
反應溫度宜依反應速度從0℃至溶劑之回流溫度之範圍選擇。尤其,使用比反應生成之醇R1
OH為更高沸點之溶劑,在比R1
OH之沸點更高溫邊餾去生成之R1
OH邊進行反應的話,從反應率提高及反應時間縮短之觀點較理想。於減壓條件進行反應時之反應壓力・溫度條件,宜為醇R1
OH揮發但產物即含氟的矽化合物(1)不揮發之條件較理想,在10Pa~100kPa、0~200℃之範圍使用適當條件尤佳。
反應時間以氣體層析(GC)等追蹤反應使反應完成的話,從產率之觀點較理想,通常約0.5~24小時。反應混合物已有充分純度時,可直接將反應混合物作為目的物操作,但視需要也可利用蒸餾、過濾、洗滌、管柱分離、固體吸附劑等各種精製法進一步精製並使用。為了去除觸媒等微量雜質使成為高純度,實施蒸餾所為之精製尤佳。
(b)法更具體而言,係使下式(3)表示之含氟化合物(1,1,1-三氟-2-(三氟甲基)- 4-戊烯-2-醇)與下列通式(4)表示之矽化合物(烷氧基氫矽烷化合物)於過渡金屬觸媒存在下加熱並使其反應。 【化12】(式中,R1
、R2
、及n同上述。)
如下列反應式所示,藉由使式(3)表示之含氟化合物與通式(4)表示之矽化合物於過渡金屬觸媒存在下加熱並使其反應,可以獲得本發明之含氟的矽化合物。 【化13】(式中,R1
、R2
、及n同上述。)
作為原料使用之矽化合物(4)不特別限定,具體而言,三甲氧基矽烷、三乙氧基矽烷、三丙氧基矽烷、三異丙氧基矽烷、甲基二甲氧基矽烷、甲基二乙氧基矽烷、甲基二異丙氧基矽烷、乙基二甲氧基矽烷、丙基二乙氧基矽烷、苯基二苯氧基矽烷、苯基二甲氧基矽烷、苯基二乙氧基矽烷、二甲氧基矽烷、二乙氧基矽烷、二異丙氧基矽烷尤佳。
含氟化合物(3)與矽化合物(4)之摻合比不特別限定,考量反應性及生產性之觀點,相對於含氟化合物(3)1莫耳,矽化合物(4)為0.5~2莫耳較理想,尤其0.7~1.3莫耳之範圍為較佳。
上述反應使用之過渡金屬觸媒,考量反應性與選擇性良好的觀點,尤其鉑觸媒為較佳。鉑觸媒可列舉氯化鉑酸、氯化鉑酸之醇溶液、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之甲苯或二甲苯溶液、肆三苯基膦鉑、二氯雙三苯基膦鉑、二氯雙乙腈鉑、二氯雙苯甲腈鉑、二氯環辛二烯鉑等。過渡金屬觸媒之使用量不特別限定,考量反應性及生產性之觀點,相對於含氟化合物(3)1莫耳,0.000001~0.01莫耳較理想,尤其0.00001~0.001莫耳之範圍為較佳。
上述反應為了提高反應速度,也可添加活性氫化合物。活性氫化合物具體而言可列舉乙醯胺、甲醯胺等醯胺類、碳酸銨、碳酸氫銨等銨鹽、甲酸、乙酸、苯甲酸等羧酸類,但無特別限定。
上述反應於無溶劑也會進行,也可使用溶劑。能使用之溶劑可列舉戊烷、己烷、環己烷、庚烷、異辛烷、苯、甲苯、二甲苯等烴系溶劑、二乙醚、四氫呋喃、二烷等醚系溶劑、乙酸乙酯、乙酸丁酯等酯系溶劑、乙腈、N,N-二甲基甲醯胺等非質子性極性溶劑、二氯甲烷、氯仿等氯系溶劑等。該等溶劑可單獨使用1種或混用2種以上。
上述反應之反應溫度不特別限定,視需要也可於反應中途升溫,30~200℃較理想,尤其50~150℃為較佳。反應時,和前述(a)法同樣邊餾去反應中生成之R1
OH邊進行反應的話,考量反應率提高及反應時間縮短之觀點更理想。
就反應時間而言,利用氣體層析(GC)等追蹤反應使反應完成的話,從產率之觀點較理想,通常約0.5~24小時。反應混合物已有充分純度時,可直接將反應混合物作為目的物操作,但視需要也可利用蒸餾、過濾、洗滌、管柱分離、固體吸附劑等各種精製法進一步精製並使用。為了去除觸媒等微量雜質使成為高純度,實施蒸餾所為之精製尤佳。
如以上,例如可利用如上述(a)法、(b)法之方法輕易地製造本發明之化合物。如此的本發明之含氟的矽化合物,保存安定性良好,且適合作為含矽中間膜形成用組成物或含矽之光阻組成物含有的樹脂(基礎樹脂)之製造原料。
[含氟的矽樹脂之製造方法] 又,本發明提供一種含氟的矽樹脂之製造方法,係將選自下列通式(5-1)表示之水解性矽化合物及下列通式(5-2)表示之反應性化合物構成之群組中之1種以上之化合物、與本發明之含氟的矽化合物之1種以上分別作為原料單體並使其水解縮合。 R3 m1
Si(OR4
)(4-m1)
(5-1) U(OR5
)m2
(OR6
)m3
(O)m4/2
(5-2) (式中,R3
各自獨立地為氫原子或碳數1~30之1價有機基。R4
各自獨立地為碳數1~6之烴基,m1為符合0≦m1≦3之整數。R5
及R6
各自獨立地為氫原子或碳數1~30之有機基。U為不包括碳與矽之周期表之III族、IV族、及V族中之任一元素。m2+m3+m4為依U之種類決定的價數,m2、m3、及m4各為0以上之整數。)
上述含氟的矽樹脂尤其適合使用在含矽中間膜形成用組成物。例如:半導體製造用微影使用之多層光阻法中,藉由使用包括以本發明之含氟的矽化合物作為原料製得之含氟的矽樹脂的含矽中間膜形成用組成物,在有機膜上已形成之含矽膜之上形成光阻膜,然後形成光阻圖案時,在乾燥、浸潤任一高NA曝光條件下皆可抑制反射,所以能形成良好的圖案。又,能於含矽膜之上層光阻膜、下層有機膜之間形成能作為良好的乾蝕刻遮罩使用的含矽膜,尤其和上層光阻之蝕刻選擇性良好,故能抑制將含矽膜乾蝕刻時之上層光阻變形。
又,上述含氟的矽樹脂適合使用在含矽之光阻組成物。上述含氟的矽樹脂於結構上有微酸性。所以,含有本發明之含氟的矽樹脂之含矽光阻組成物,和光阻之圖案形成時使用之鹼顯影液間的親和性高,能抑制圖案顯影時之顯影不足導致之缺陷發生。另一方面,並非過度酸性,不不會促進過顯影引起之圖案崩塌,適合使用在含矽之光阻組成物。
前述通式(5-1)中,R3
各自獨立地為氫原子或碳數1~30之1價有機基。R3
更具體而言宜為氫原子、甲基、乙基、苯基、己基、癸基、三氟丙基、乙烯基、2-(3,4-環氧環己基)乙基、3-環氧丙氧基丙基、3-甲基丙烯醯氧丙基、3-(2-胺基乙胺基)丙基、3-胺基丙基、N-苯基-3-胺基丙基、3-氯丙基、3-巰基丙基、甲苯基、二甲苯基、氟苯基、二氟苯基、第三丁氧基苯基、苯乙基、苄基尤佳但不限定於此等。
前述通式(5-1)中,R4
各自獨立地為碳數1~6之烴基,更具體而言,甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、己基、環己基、苯基、烯丙基尤佳但不限定於此等。
前述通式(5-1)中,m1為符合0≦m1≦3之整數,0、1、或2較佳,0或1尤佳。
前述通式(5-1)表示之水解性矽化合物更體而言可列舉以下的化合物,但不限定於此等。
四烷氧基矽烷,例如:四甲氧基矽烷、四乙氧基矽烷、四丙氧基矽烷、四異丙氧基矽烷。
三烷氧基矽烷,例如:三甲氧基矽烷、三乙氧基矽烷、三丙氧基矽烷、三異丙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三丙氧基矽烷、甲基三異丙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙基三丙氧基矽烷、乙基三異丙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三丙氧基矽烷、乙烯基三異丙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丙基三丙氧基矽烷、丙基三異丙氧基矽烷、異丙基三甲氧基矽烷、異丙基三乙氧基矽烷、異丙基三丙氧基矽烷、異丙基三異丙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、丁基三丙氧基矽烷、丁基三異丙氧基矽烷、第二丁基三甲氧基矽烷、第二丁基三乙氧基矽烷、第二丁基三丙氧基矽烷、第二丁基三異丙氧基矽烷、第三丁基三甲氧基矽烷、第三丁基三乙氧基矽烷、第三丁基三丙氧基矽烷、異丁基三甲氧基矽烷、異丁基三乙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、環丙基三甲氧基矽烷、環丙基三乙氧基矽烷、環丙基三丙氧基矽烷、環丙基三異丙氧基矽烷、環丁基三甲氧基矽烷、環丁基三乙氧基矽烷、環丁基三丙氧基矽烷、環丁基三異丙氧基矽烷、環戊基三甲氧基矽烷、環戊基三乙氧基矽烷、環戊基三丙氧基矽烷、環戊基三異丙氧基矽烷、環己基三甲氧基矽烷、環己基三乙氧基矽烷、環己基三丙氧基矽烷、環己基三異丙氧基矽烷、環己烯基三甲氧基矽烷、環己烯基三乙氧基矽烷、環己烯基三丙氧基矽烷、環己烯基三異丙氧基矽烷、環己烯基乙基三甲氧基矽烷、環己烯基乙基三乙氧基矽烷、環己烯基乙基三丙氧基矽烷、環己烯基乙基三異丙氧基矽烷、環辛基三甲氧基矽烷、環辛基三乙氧基矽烷、環辛基三丙氧基矽烷、環辛基三異丙氧基矽烷、環戊二烯基丙基三甲氧基矽烷、環戊二烯基丙基三乙氧基矽烷、環戊二烯基丙基三丙氧基矽烷、環戊二烯基丙基三異丙氧基矽烷、雙環庚烯基三甲氧基矽烷、雙環庚烯基三乙氧基矽烷、雙環庚烯基三丙氧基矽烷、雙環庚烯基三異丙氧基矽烷、雙環庚基三甲氧基矽烷、雙環庚基三乙氧基矽烷、雙環庚基三丙氧基矽烷、雙環庚基三異丙氧基矽烷、金剛烷基三甲氧基矽烷、金剛烷基三乙氧基矽烷、金剛烷基三丙氧基矽烷、金剛烷基三異丙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、苯基三丙氧基矽烷、苯基三異丙氧基矽烷、苄基三甲氧基矽烷、苄基三乙氧基矽烷、苄基三丙氧基矽烷、苄基三異丙氧基矽烷、甲苯基三甲氧基矽烷、甲苯基三乙氧基矽烷、甲苯基三丙氧基矽烷、甲苯基三異丙氧基矽烷、苯乙基三甲氧基矽烷、苯乙基三乙氧基矽烷、苯乙基三丙氧基矽烷、苯乙基三異丙氧基矽烷、萘基三甲氧基矽烷、萘基三乙氧基矽烷、萘基三丙氧基矽烷、萘基三異丙氧基矽烷。
二烷氧基矽烷,例如:二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、二甲基二丙氧基矽烷、二甲基二異丙氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、二乙基二丙氧基矽烷、二乙基二異丙氧基矽烷、二丙基二甲氧基矽烷、二丙基二乙氧基矽烷、二丙基二丙氧基矽烷、二丙基二異丙氧基矽烷、二異丙基二甲氧基矽烷、二異丙基二乙氧基矽烷、二異丙基二丙氧基矽烷、二異丙基二異丙氧基矽烷、二丁基二甲氧基矽烷、二丁基二乙氧基矽烷、二丁基二丙氧基矽烷、二丁基二異丙氧基矽烷、二第二丁基二甲氧基矽烷、二第二丁基二乙氧基矽烷、二第二丁基二丙氧基矽烷、二第二丁基二異丙氧基矽烷、二第三丁基二甲氧基矽烷、二第三丁基二乙氧基矽烷、二第三丁基二丙氧基矽烷、二第三丁基二異丙氧基矽烷、二環丙基二甲氧基矽烷、二環丙基二乙氧基矽烷、二環丙基二丙氧基矽烷、二環丙基二異丙氧基矽烷、二環丁基二甲氧基矽烷、二環丁基二乙氧基矽烷、二環丁基二丙氧基矽烷、二環丁基二異丙氧基矽烷、二環戊基二甲氧基矽烷、二環戊基二乙氧基矽烷、二環戊基二丙氧基矽烷、二環戊基二異丙氧基矽烷、二環己基二甲氧基矽烷、二環己基二乙氧基矽烷、二環己基二丙氧基矽烷、二環己基二異丙氧基矽烷、二環己烯基二甲氧基矽烷、二環己烯基二乙氧基矽烷、二環己烯基二丙氧基矽烷、二環己烯基二異丙氧基矽烷、二環己烯基乙基二甲氧基矽烷、二環己烯基乙基二乙氧基矽烷、二環己烯基乙基二丙氧基矽烷、二環己烯基乙基二異丙氧基矽烷、二環辛基二甲氧基矽烷、二環辛基二乙氧基矽烷、二環辛基二丙氧基矽烷、二環辛基二異丙氧基矽烷、二環戊二烯基丙基二甲氧基矽烷、二環戊二烯基丙基二乙氧基矽烷、二環戊二烯基丙基二丙氧基矽烷、二環戊二烯基丙基二異丙氧基矽烷、雙(雙環庚烯基)二甲氧基矽烷、雙(雙環庚烯基)二乙氧基矽烷、雙(雙環庚烯基)二丙氧基矽烷、雙(雙環庚烯基)二異丙氧基矽烷、雙(雙環庚基)二甲氧基矽烷、雙(雙環庚基)二乙氧基矽烷、雙(雙環庚基)二丙氧基矽烷、雙(雙環庚基)二異丙氧基矽烷、雙金剛烷基二甲氧基矽烷、雙金剛烷基二乙氧基矽烷、雙金剛烷基二丙氧基矽烷、雙金剛烷基二異丙氧基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、二苯基二丙氧基矽烷、二苯基二異丙氧基矽烷。
一烷氧基矽烷,例如:三甲基甲氧基矽烷、三甲基乙氧基矽烷、二甲基乙基甲氧基矽烷、二甲基乙基乙氧基矽烷、二甲基苯基甲氧基矽烷、二甲基苯基乙氧基矽烷、二甲基苄基甲氧基矽烷、二甲基苄基乙氧基矽烷、二甲基苯乙基甲氧基矽烷、二甲基苯乙基乙氧基矽烷。
更佳為四甲氧基矽烷、四乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、異丙基三甲氧基矽烷、異丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、異丁基三甲氧基矽烷、異丁基三乙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、環戊基三甲氧基矽烷、環戊基三乙氧基矽烷、環己基三甲氧基矽烷、環己基三乙氧基矽烷、環己烯基三甲氧基矽烷、環己烯基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、苄基三甲氧基矽烷、苄基三乙氧基矽烷、苯乙基三甲氧基矽烷、苯乙基三乙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、二丙基二甲氧基矽烷、二丁基二甲氧基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、三甲基甲氧基矽烷、二甲基乙基甲氧基矽烷、二甲基苯基甲氧基矽烷、二甲基苄基甲氧基矽烷、二甲基苯乙基甲氧基矽烷。
前述通式(5-2)中,U為不包括碳與矽之周期表之III族、IV族、及V族中之任一元素。U更具體而言為硼、鋁、鎵、釔、鍺、鈦、鋯、鉿、鉍、錫、磷、釩、砷、銻、鈮、及鉭尤佳。
含有上述U所示之金屬的含氟的矽樹脂,比起不含該等金屬之含氟的矽樹脂,有以下好處:例如使用在多層微影用中間膜時,中間膜的蝕刻速度較快,即使是將更薄膜化之光阻作為蝕刻遮罩仍能形成可轉印圖案之中間膜。
前述通式(5-2)中,R5
及R6
各自獨立地為氫原子或碳數1~30之有機基。R5
及R6
更具體而言為氫原子、甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、己基、環己基、苯基、烯丙基、苄基、苯乙基、二十基、二十三基尤佳,但不限定於此等。
前述通式(5-2)中,m2+m3+m4為依U之種類決定的價數,m2、m3、及m4各0以上之整數。例如:典型者為U為鈦、鋯、鉿、鍺、錫、鉛的情形,m2+m3+m4=4,U為釩、鈮、鉭的情形,m2+m3+m4=5,U為磷、砷、銻、鉍的情形,m2+m3+m4=3或5,U為硼、鋁、鎵、釔、銦、鉈的情形,m2+m3+m4=3。
前述通式(5-2)表示之反應性化合物可列舉如下的化合物,但不限定於此等。
例如:U為硼的情形可列舉:甲氧化硼、乙氧化硼、丙氧化硼、異丙氧化硼、丁氧化硼、戊氧化硼、己氧化硼、環戊氧化硼、環己氧化硼、烯丙氧化硼、苯氧化硼、甲氧基乙氧化硼基、硼酸、氧化硼等。
U為鋁的情形,可列舉甲氧化鋁、乙氧基化鋁、丙氧化鋁、異丙氧化鋁、丁氧化鋁、戊氧化鋁、己氧化鋁、環戊氧化鋁、環己氧化鋁、烯丙氧化鋁、苯氧化鋁、甲氧基乙氧化鋁、乙氧基乙氧化鋁、二丙氧基乙基乙醯乙酸鋁、二丁氧基乙基乙醯乙酸鋁、丙氧基雙乙基乙醯乙酸鋁、丁氧基雙乙基乙醯乙酸鋁、2,4-戊二酮酸鋁、2,2,6,6-四甲基-3,5-庚二酮酸鋁。
U為鎵的情形,可列舉:甲氧化鎵、乙氧化鎵、丙氧化鎵、異丙氧化鎵、丁氧化鎵、戊氧化鎵、己氧化鎵、環戊氧化鎵、環己氧化鎵、烯丙氧化鎵、苯氧化鎵、甲氧基乙氧化鎵、乙氧基乙氧化鎵、二丙氧基乙基乙醯乙酸鎵、二丁氧基乙基乙醯乙酸鎵、丙氧基雙乙基乙醯乙酸鎵、丁氧基雙乙基乙醯乙酸鎵、2,4-戊二酮鎵、2,2,6,6-四甲基-3,5-庚二酮酸鎵。
U為釔的情形可列舉:甲氧化釔、乙氧化釔、丙氧化釔、異丙氧化釔、丁氧化釔、戊氧化釔、己氧化釔、環戊氧化釔、環己氧化釔、烯丙氧化釔、苯氧化釔、甲氧基乙氧化釔、乙氧基乙氧化釔、二丙氧基乙基乙醯乙酸釔、二丁氧基乙基乙醯乙酸釔、丙氧基雙乙基乙醯乙酸釔、丁氧基雙乙基乙醯乙酸釔、2,4-戊二酮酸釔、2,2,6,6-四甲基-3,5-庚二酮酸釔。
U為鍺的情形可列舉:甲氧化鍺、乙氧化鍺、丙氧化鍺、異丙氧化鍺、丁氧化鍺、戊氧化鍺、己氧化鍺、環戊氧化鍺、環己氧化鍺、烯丙氧化鍺、苯氧化鍺、甲氧基乙氧化鍺、乙氧基乙氧化鍺。
U為鈦的情形可列舉:甲氧化鈦、乙氧化鈦、丙氧化鈦、異丙氧化鈦、丁氧化鈦、戊氧化鈦、己氧化鈦、環戊氧化鈦、環己氧化鈦、烯丙氧化鈦、苯氧化鈦、甲氧基乙氧化鈦、乙氧基乙氧化鈦、二丙氧基雙乙基乙醯乙酸鈦、二丁氧基雙乙基乙醯乙酸鈦、二丙氧基雙2,4-戊二酮酸鈦、二丁氧基雙2,4-戊二酮酸鈦。
U為鋯的情形可列舉:甲氧化鋯、乙氧化鋯、丙氧化鋯、異丙氧化鋯、丁氧化鋯、苯氧化鋯、二丁氧基雙(2,4-戊二酮酸)鋯、二丙氧基雙(2,2,6,6-四甲基-3,5-庚烷酮酸)鋯。
U為鉿的情形可列舉:甲氧化鉿、乙氧化鉿、丙氧化鉿、異丙氧化鉿、丁氧化鉿、戊氧化鉿、己氧化鉿、環戊氧化鉿、環己氧化鉿、烯丙氧化鉿、苯氧化鉿、甲氧基乙氧化鉿、乙氧基乙氧化鉿、二丙氧基雙乙基乙醯乙酸鉿、二丁氧基雙乙基乙醯乙酸鉿、二丙氧基雙2,4-戊二酮酸鉿、二丁氧基雙2,4-戊二酮酸鉿。
U為鉍的情形可列舉甲氧基鉍、乙氧基鉍、異丙氧基鉍、丁氧基鉍、苯氧基鉍。
U為錫的情形可列舉甲氧化錫、乙氧化錫、異丙氧化錫、丁氧化錫、苯氧化錫、甲氧基乙氧化錫、乙氧基乙氧化錫、2,4-戊二酮酸錫、2,2,6,6-四甲基-3,5-庚二酮酸錫。
U為磷的情形,可列舉:亞磷酸三甲酯、亞磷酸三乙酯、亞磷酸三異丙酯、磷酸三甲酯、磷酸三乙酯、磷酸三丙酯、五氧化二磷、磷酸、亞磷酸、多酸。
U為釩的情形可列舉:雙(2、4-戊二酮酸) 氧化釩、2、4-戊二酮酸釩、三丁氧基氧化釩、三異丙氧基氧化釩。
U為砷的情形可列舉:甲氧化砷、乙氧化砷、異丙氧化砷、丁氧化砷、苯氧化砷。
U為銻的情形可列舉甲氧化銻、乙氧化銻、異丙氧化銻、丁氧化銻、苯氧化銻、乙酸銻、丙酸銻。
U為鈮的情形可列舉甲氧化鈮、乙氧化鈮、異丙氧化鈮、丁氧化鈮、苯氧化鈮。
U為鉭的情形可列舉甲氧化鉭、乙氧化鉭、異丙氧化鉭、丁氧化鉭、苯氧化鉭。
可將如此的前述通式(1)表示之含氟的矽化合物的1種以上、與選擇由前述通式(5-1)表示之水解性矽化合物與前述通式(5-2)表示之反應性化合物構成的群中的1種以上之化合物,於反應前或反應中混合成為形成含氟的矽樹脂的反應原料。
理想的製造條件列舉如下條件,但不限於此條件。含氟的矽樹脂可藉由將前述通式(1)表示之含氟的矽化合物之1種以上、與選自由前述通式(5-1)表示之水解性矽化合物及前述通式(5-2)表示之反應性化合物之群中之1種以上之化合物(以下稱為「單體」),使用選自酸,較佳為無機酸、磺酸衍生物(脂肪族磺酸及芳香族磺酸)中之1種以上作為觸媒進行水解縮合以製造。
此時使用之酸觸媒,具體而言可列舉氟酸、鹽酸、溴化氫酸、硫酸、硝酸、過氯酸、磷酸、甲烷磺酸、苯磺酸、甲苯磺酸等。觸媒之使用量較佳為相對於單體1莫耳為10-6
~10莫耳,更佳為10-5
~5莫耳,又更佳為10-4
~1莫耳。
從該等單體利用水解縮合獲得含氟的矽樹脂時,添加之水之量較佳為鍵結於單體之水解性取代基每1莫耳為0.01~100莫耳,更佳為0.05~50莫耳,又更佳為0.1~30莫耳。若添加100莫耳以下,反應使用之裝置不會變得過大,為經濟的。
操作方法,例如可藉由於觸媒水溶液添加單體使水解縮合反應開始。此時可在觸媒水溶液添加有機溶劑,也可將單體以有機溶劑先稀釋,也可進行兩者。反應溫度宜為0~100℃,更佳為5~80℃。尤其,單體滴加時保持溫度5~80℃,之後於20~80℃使其熟成之方法較佳。
可添加在觸媒水溶液、或能將單體稀釋之有機溶劑可列舉甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、乙腈、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基異丁酮、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇一第三丁醚乙酸酯、γ-丁內酯及該等之混合物為較佳。
該等溶劑之中理想者為水溶性者。例如:甲醇、乙醇、1-丙醇、2-丙醇等醇類、乙二醇、丙二醇等多元醇、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇一丙醚、丙二醇一丙醚、乙二醇一丙醚等多元醇縮合物衍生物、丙酮、乙腈、四氫呋喃等。其中尤其理想者為沸點100℃以下者。
又,有機溶劑之使用量相對於單體1莫耳宜為0~1,000mL較理想,尤其0~500 mL為較佳。有機溶劑之使用量若為此範圍,無需過大的反應容器,能經濟地進行反應。
之後若有必要,進行觸媒之中和反應,將水解縮合反應生成之醇減壓除去並獲得反應混合物之水溶液。此時中和能使用之鹼性物質之量,相對於觸媒使用之酸宜為0.1~2當量較佳。此鹼性物質只要是在水中呈鹼性即可,可使用任意物質。
然後宜從反應混合物將水解縮合反應生成之醇等副生物去除較佳。此時將反應混合物加熱之溫度,取決於已添加之有機溶劑及反應產生之醇等的種類,較佳為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時之減壓度取決於待除去之有機溶劑及醇等種類、排氣裝置、冷凝裝置、及加熱溫度而異,較佳為在大氣壓以下,更佳為絕對壓力80kPa以下,更佳為絕對壓力50kPa以下。此時除去之醇量難以正確查知,但希望去除生成之醇等約80質量%以上。
然後,也可從反應混合物去除水解縮合使用之酸觸媒。去除酸觸媒之方法可列舉將水與含氟的矽樹脂混合,並以有機溶劑萃取含氟的矽樹脂的方法。此時使用之有機溶劑宜為能溶解含氟的矽樹脂,且若和水混合會分層為2層者較佳。例如甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基異丁酮、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇一丙醚、丙二醇一丙醚、乙二醇一丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇一第三丁醚乙酸酯、γ-丁內酯、環戊基甲醚等及該等之混合物。
再者,也可以使用水溶性有機溶劑與水難溶性有機溶劑之混合物。例如甲醇+乙酸乙酯、乙醇+乙酸乙酯、1-丙醇+乙酸乙酯、2-丙醇+乙酸乙酯、丁二醇單甲醚+乙酸乙酯、丙二醇單甲醚+乙酸乙酯、乙二醇單甲醚+乙酸乙酯、丁二醇單乙醚+乙酸乙酯、丙二醇單乙醚+乙酸乙酯、乙二醇單乙醚+乙酸乙酯、丁二醇一丙醚+乙酸乙酯、丙二醇一丙醚+乙酸乙酯、乙二醇一丙醚+乙酸乙酯、甲醇+甲基異丁酮、乙醇+甲基異丁酮、1-丙醇+甲基異丁酮、2-丙醇+甲基異丁酮、丙二醇單甲醚+甲基異丁酮、乙二醇單甲醚+甲基異丁酮、丙二醇單乙醚+甲基異丁酮、乙二醇單乙醚+甲基異丁酮、丙二醇一丙醚+甲基異丁酮、乙二醇一丙醚+甲基異丁酮、甲醇+環戊基甲醚、乙醇+環戊基甲醚、1-丙醇+環戊基甲醚、2-丙醇+環戊基甲醚、丙二醇單甲醚+環戊基甲醚、乙二醇單甲醚+環戊基甲醚、丙二醇單乙醚+環戊基甲醚、乙二醇單乙醚+環戊基甲醚、丙二醇一丙醚+環戊基甲醚、乙二醇一丙醚+環戊基甲醚、甲醇+丙二醇甲醚乙酸酯、乙醇+丙二醇甲醚乙酸酯、1-丙醇+丙二醇甲醚乙酸酯、2-丙醇+丙二醇甲醚乙酸酯、丙二醇單甲醚+丙二醇甲醚乙酸酯、乙二醇單甲醚+丙二醇甲醚乙酸酯、丙二醇單乙醚+丙二醇甲醚乙酸酯、乙二醇單乙醚+丙二醇甲醚乙酸酯、丙二醇一丙醚+丙二醇甲醚乙酸酯、乙二醇一丙醚+丙二醇甲醚乙酸酯等組合為較佳但不限定於此等。
又,水溶性有機溶劑與水難溶性有機溶劑之混合比例可適當選擇,相對於水難溶性有機溶劑100質量份較佳為水溶性有機溶劑0.1~1,000質量份,更佳為1~ 500質量份,又更佳為2~100質量份。
然後為了去除酸觸媒等水溶性雜質,也可用中性水洗滌。此水可使用通常稱為去離子水、超純水者。洗滌水之量相對於含氟的矽樹脂溶液1L較佳為0.01~ 100L,更佳為0.05~50L,又更佳為0.1~5L。洗滌方法可為將含氟的矽樹脂溶液與洗滌水兩者在同一容器內攪動後靜置並分離水層。洗滌次數為1次以上即可,但即便洗滌10次以上也不一定會獲得相應洗滌次數的效果,較佳為1~5次。
此外去除酸觸媒之方法可列舉利用離子交換樹脂之方法、利用環氧乙烷、環氧丙烷等環氧化合物中和後去除之方法。該等方法可配合反應使用之酸觸媒適當選擇。
又,上述觸媒除去操作時,反應使用之酸觸媒宜去除直到減低至含氟的矽樹脂溶液中,相對於反應開始時添加之量成為10質量%以下,較佳為5質量%以下左右較佳。
由於此時之水洗操作,有一部分的含氟的矽樹脂進入水層,有時實質上獲得和分級操作同等之效果,故水洗次數、洗滌水之量可考慮觸媒除去效果及分級效果而適當選擇。
有酸觸媒殘留之含氟的矽樹脂及已去除酸觸媒之含氟的矽樹脂溶液均可藉由添加最終溶劑並於減壓進行溶劑交換而獲得含氟的矽樹脂溶液。此時溶劑交換之溫度取決於待除去之反應溶劑、萃取溶劑之種類,較佳為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時之減壓度取決於待除去之萃取溶劑之種類、排氣裝置、冷凝裝置、及加熱溫度而異,較佳為於大氣壓以下,更佳為絕對壓力80kPa以下,又更佳為絕對壓力50kPa以下。
此時有時因為改變溶劑會造成含氟的矽樹脂變得不安定。此現象是因為最終溶劑與含氟的矽樹脂之相容性而造成,為了防止此現象,可以添加後述安定劑。加入量宜相對於溶劑交換前之溶液中之含氟的矽樹脂100質量份為0~25質量份,更佳為0~15質量份,又更佳為0~5質量份,添加時為0.5質量份以上較佳。溶劑交換前之溶液中,可視需要添加安定劑而進行溶劑交換操作。
又,含氟的矽樹脂溶液宜為適當濃度的溶液狀態,0.1~20質量%之濃度較佳。若為20質量%以下,不會發生含氟的矽樹脂之縮合反應且變成對於有機溶劑無法再溶解之狀態。又,若為0.1質量%以上,可防止溶劑之量過多而變成不經濟。
加到含氟的矽樹脂溶液之最終溶劑,理想者醇系溶劑,尤其理想者為乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇、丁二醇等一烷醚衍生物。具體而言,丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇一丙醚、丙二醇一丙醚、乙二醇一丙醚等為較佳。
該等溶劑為主成分即可,可添加非醇系溶劑作為輔助溶劑。輔助溶劑可列舉丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基異丁酮、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇一第三丁醚乙酸酯、γ-丁內酯、環戊基甲醚等。
又,作為其他反應操作,係於單體或單體之有機溶液添加水或含水有機溶劑並使水解反應開始。此時觸媒可添加到單體或單體之有機溶液,也可添加到水或含水有機溶劑。反應溫度為0~100℃,較佳為10~80℃。宜為水滴加時加熱到10~50℃,之後升溫到20~80℃並使其熟成之方法較佳。
使用有機溶劑時,宜為水溶性者較理想,可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇等醇類、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇一丙醚、丙二醇一丙醚、乙二醇一丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇一丙醚等多元醇縮合物衍生物、丙酮、四氫呋喃、乙腈及該等之混合物等。
有機溶劑之使用量可以和上述量相同。可對於獲得之反應混合物以和上述為同樣方法實施後處理,獲得含氟的矽樹脂。
獲得之含氟的矽樹脂之重量平均分子量不只可利用單體選擇,也可利用聚合時之反應條件控制調整,較佳為100,000以下,更佳為200~50,000,又更佳為300~30,000。重量平均分子量若為100,000以下,可抑制異物、塗佈斑出現。
又,上述關於重量平均分子量之數據,係使用RI作為檢測器,利用凝膠滲透層析(GPC),並使用聚苯乙烯作為標準物質,以聚苯乙烯換算表達分子量。
為了確保獲得之含氟的矽樹脂之安定性,可添加碳數為1~30之1價或2價以上之有機酸作為安定劑。此時添加之有機酸可列舉:甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、油酸、硬脂酸、亞油酸、亞油烯酸、苯甲酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、水楊酸、三氟乙酸、一氯乙酸、二氯乙酸、三氯乙酸、草酸、丙二酸、甲基丙二酸、乙基丙二酸、丙基丙二酸、丁基丙二酸、二甲基丙二酸、二乙基丙二酸、琥珀酸、甲基琥珀酸、戊二酸、己二酸、衣康酸、馬來酸、富馬酸、檸康酸、檸檬酸等。尤其草酸、馬來酸、甲酸、乙酸、丙酸、檸檬酸等為較佳。又,為了確保安定性,也可混用2種以上之有機酸。
添加有機酸時之添加量,於含氟的矽樹脂使用在含矽中間膜形成用組成物、含矽之光阻組成物時,較佳為相對於該等組成物所含之含氟的矽樹脂100質量份,為0.001~25質量份,更佳為0.01~15質量份,又更佳為0.1~5質量份。或宜以換算為該等組成物之pH,成為較佳為0≦pH≦7,更佳為0.3≦pH≦6.5,又更佳為0.5≦pH≦6之方式摻合上述有機酸。 [實施例]
以下舉實施例及比較例對於本發明具體説明,但本發明不限於下列實施例。
本發明之含氟的矽化合物依以下所示方法合成。 [實施例1-1]2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)之合成1 【化14】將裝有1,1,1-三氟-5-(三乙氧基矽基)-2-(三氟甲基)-2-戊醇(2A)93.1g、甲苯50g之燒瓶加熱,進行30分鐘全回流後,費時20小時逐步地餾去輕沸分。冷卻後以減壓蒸餾進行精製,獲得2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)65.3g。沸點:74℃/1,100Pa。
獲得之目的物之紅外吸收(IR)光譜及核磁共振(1
H-NMR、13
C-NMR、19
F-NM R)光譜之測定結果如下所示。 IR(D-ATR):ν=2980、2935、2894、1451、1390、1331、1307、1279、1255、1213、1186、1169、1132、1106、1073、1002、956、912、875、818、798、776、711、672cm-1
。1
H-NMR(600MHz、CDCl3
):δ=0.80(2H、t、J=7.0Hz)、1.23(6H、t、J=7.0Hz)、1.92-2.02(4H、m)、3.85(4H、q、J=7.0Hz)。13
C-NMR(150MHz、CDCl3
):δ=7.41、17.01、17.77、27.02、58.90、78.82(sep、J=29Hz)、123.13(q、J=287Hz)。19
F-NMR(565MHz、CDCl3
):δ=-78.81(6F、s)。
[實施例1-2]2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)之合成2 【化15】將1,1,1-三氟-2-(三氟甲基)-4-戊烯-2-醇(3)208g、鉑-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之甲苯溶液(鉑含量3質量%)1.3g、庚烷200g之混合物加熱到約100℃,費時20小時邊餾去反應生成的乙醇邊滴加三乙氧基矽烷(4A)172g。加熱直到乙醇之餾去結束後冷卻。實施利用減壓蒸餾之精製,獲得2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)196g。沸點:74℃/1,100Pa。
獲得之目的物之紅外吸收(IR)光譜及核磁共振(1
H-NMR、13
C-NMR、19
F-NM R)光譜之測定結果如下所示。 IR(D-ATR):ν=2980、2935、2894、1451、1390、1331、1307、1279、1255、1213、1186、1169、1132、1106、1073、1002、956、912、875、818、798、776、711、672cm-1
。1
H-NMR(600MHz、CDCl3
):δ=0.80(2H、t、J=7.0Hz)、1.23(6H、t、J=7.0Hz)、1.92-2.02(4H、m)、3.85(4H、q、J=7.0Hz)。13
C-NMR(150MHz、CDCl3
):δ=7.41、17.01、17.77、27.02、58.90、78.82(sep、J=29Hz)、123.13(q、J=287Hz)。19
F-NMR(565MHz、CDCl3
):δ=-78.81(6F、s)。
[實施例1-3]2,2-二甲氧基-6,6-雙(三氟甲基)oxasiline(1B)之合成 【化16】將原料變更為1,1,1-三氟-5-(三甲氧基矽基)-2-(三氟甲基)-2-戊醇(2B),除此以外依據實施例1之方法獲得2,2-二甲氧基-6,6-雙(三氟甲基)oxasiline(1B)。
[實施例1-4]2-乙氧基-2-甲基-6,6-雙(三氟甲基)oxasiline(1C)之合成 【化17】將原料變更為1,1,1-三氟-5-(二乙氧基甲基矽基)-2-(三氟甲基)-2-戊醇(2C),除此以外依實施例1之方法獲得2-乙氧基-2-甲基-6,6-雙(三氟甲基)oxasiline(1C)。
[實施例1-5]2-甲氧基-2-苯基-6,6-雙(三氟甲基)oxasiline(1D)之合成 【化18】將原料變更為1,1,1-三氟-5-(二甲氧基苯基矽基)-2-(三氟甲基)-2-戊醇(2D),除此以外依實施例1之方法獲得2-甲氧基-2-苯基-6,6-雙(三氟甲基)oxasiline(1D)。
使用實施例1-1~1-5合成之含氟的矽化合物,以本發明之製造方法製造含氟的矽樹脂。 [實施例2-1]Polymer-1之合成 於乙醇120g、70%硝酸1g、及去離子水60g之混合物添加2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)8.2g、四乙氧基矽烷84.2g、甲基三甲氧基矽烷3.4g、及苯基三甲氧基矽烷10.0g之混合物,於40℃保持12小時,使其進行水解縮合。反應結束後加入PGEE(丙二醇單乙醚)400g,將副生醇及過量的水於減壓餾去,獲得下列平均組成式表示之Polymer-1之PGEE溶液400g(聚合物濃度10%)。依GPC分析測定此Polymer-1之聚苯乙烯換算分子量,結果為Mw=2,900、分散度Mw/Mn =2.12。 【化19】
[實施例2-2]Polymer-2之合成 於乙醇120g、五氧化磷1.8g、70%硝酸1g、及去離子水60g之混合物中添加2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)8.5g、四乙氧基矽烷81.3g、苯基三甲氧基矽烷10.3g、及硼酸三甲基2.7g之混合物,於40℃保持12小時,使其水解縮合。反應結束後加入PGEE 400g,將副生醇及過量的水於減壓餾去,獲得下列平均組成式表示之Polymer-2之PGEE溶液400g(聚合物濃度10%)。測定此Polymer-2之聚苯乙烯換算分子量,結果為Mw=3,100、分散度Mw/Mn=2.23。 【化20】
[實施例2-3~2-5]Polymer-3~Polymer-5之合成 將實施例2-1之2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)分別變更為2,2-二甲氧基-6,6-雙(三氟甲基)oxasiline(1B)、2-乙氧基-2-甲基-6,6-雙(三氟甲基)oxasi line(1C)、2-甲氧基-2-苯基-6,6-雙(三氟甲基)oxasiline(1D),除此以外和實施例2-1同樣合成含氟的矽樹脂,獲得Polymer-3~Polymer-5。
如實施例1-1~1-5、及實施例2-1~2-5,確認:本發明之含氟的矽化合物製造容易,且作為以水解縮合製造之含氟的矽樹脂之原料單體為有用。
[保存安定性試驗] 測定實施例1-1合成之2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)剛蒸餾精製時之GC-FID純度(保存前之純度),並同樣測定既有之含氟的矽化合物(比較例1)1,1,1-三氟-5-(三乙氧基矽基)-2-(三氟甲基)-2-戊醇(亦即下式(6)表示之化合物)之GC-FID純度(保存前之純度)。然後將其於氮氣環境下於室溫保存5個月,測定保存後之純度。其結果,既有的含氟的矽化合物1,1,1-三氟-5-(三乙氧基矽基)-2- (三氟甲基)-2-戊醇(比較例1)的保存前純度為93.2%、保存後純度為57.8%,而本發明之含氟的矽化合物2,2-二乙氧基-6,6-雙(三氟甲基)oxasiline(1A)(實施例1-1)之保存前純度為98.5%、保存後純度為98.8%。 【化21】
由上述結果可知:本發明之含氟的矽化合物比起在同樣用途使用之既有含氟的矽化合物,保存安定性大幅提高,啟示其工業利用價値高。
又,本發明不限於上述實施形態。上述實施形態為例示,若和本發明之申請專利範圍記載之技術思想有實質上同構成且發揮同樣作用效果者皆包括在本發明之技術範圍。
無
Claims (5)
- 一種含氟的矽化合物,以下列通式(1)表示; 【化1】式中,R1 各自獨立地為碳數1~6之烴基,R2 各自獨立地為氫原子或碳數1~6之烴基;n為符合0≦n≦2之整數。
- 如申請專利範圍第1項之含氟的矽化合物,其中,該含氟的矽化合物係成為含矽中間膜形成用組成物或含矽之光阻組成物所含之樹脂之製造原料。
- 一種含氟的矽化合物之製造方法,係製造如申請專利範圍第1或2項之含氟的矽化合物; 其特徵為:使下列通式(2)表示之含氟的矽化合物進行分子內縮合; 【化2】式中,R1 、R2 、及n同上述。
- 一種含氟的矽化合物之製造方法,係製造如申請專利範圍第1或2項之含氟的矽化合物; 其特徵為:使下式(3)表示之含氟化合物與下列通式(4)表示之矽化合物反應; 【化3】式中,R1 、R2 、及n同上述。
- 一種含氟的矽樹脂之製造方法,其特徵為: 使選自由下列通式(5-1)表示之水解性矽化合物及下列通式(5-2)表示之反應性化合物構成之群之1種以上之化合物,與如申請專利範圍第1或2項之含氟的矽化合物之1種以上進行水解縮合; R3 m1 Si(OR4 )(4-m1) (5-1) U(OR5 )m2 (OR6 )m3 (O)m4/2 (5-2) 式中,R3 各自獨立地為氫原子或碳數1~30之1價有機基;R4 各自獨立地為碳數1~6之烴基,m1為符合0≦m1≦3之整數;R5 及R6 各自獨立地為氫原子或碳數1~30之有機基;U為不包括碳與矽之周期表之III族、IV族、及V族中之任一元素;m2+m3+m4為依U之種類決定的價數,m2、m3、及m4各為0以上之整數。
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