KR101095746B1 - 절연막 및 그의 형성 방법, 및 막 형성용 조성물 - Google Patents
절연막 및 그의 형성 방법, 및 막 형성용 조성물 Download PDFInfo
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- KR101095746B1 KR101095746B1 KR1020067014379A KR20067014379A KR101095746B1 KR 101095746 B1 KR101095746 B1 KR 101095746B1 KR 1020067014379 A KR1020067014379 A KR 1020067014379A KR 20067014379 A KR20067014379 A KR 20067014379A KR 101095746 B1 KR101095746 B1 KR 101095746B1
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- insulating film
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- 238000000034 method Methods 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title abstract description 66
- -1 polysiloxane Polymers 0.000 claims abstract description 154
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 229920003257 polycarbosilane Polymers 0.000 claims abstract description 65
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 65
- 239000002904 solvent Substances 0.000 claims abstract description 46
- 238000000576 coating method Methods 0.000 claims abstract description 37
- 239000011248 coating agent Substances 0.000 claims abstract description 34
- 238000009833 condensation Methods 0.000 claims abstract description 9
- 230000005494 condensation Effects 0.000 claims abstract description 9
- 229910000077 silane Inorganic materials 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims abstract description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 6
- 125000000962 organic group Chemical group 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229920000412 polyarylene Polymers 0.000 claims description 6
- 125000001174 sulfone group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229920000765 poly(2-oxazolines) Polymers 0.000 claims description 3
- 230000009977 dual effect Effects 0.000 abstract description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 52
- 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 44
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 40
- 125000000217 alkyl group Chemical group 0.000 description 31
- 125000003118 aryl group Chemical group 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000006116 polymerization reaction Methods 0.000 description 22
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 21
- 239000010936 titanium Substances 0.000 description 21
- 229910052719 titanium Inorganic materials 0.000 description 21
- 229910052763 palladium Inorganic materials 0.000 description 20
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- 229910052726 zirconium Inorganic materials 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 239000010410 layer Substances 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 238000004528 spin coating Methods 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
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- 238000005530 etching Methods 0.000 description 14
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 14
- 239000003446 ligand Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 10
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000001020 plasma etching Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000011229 interlayer Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229910052723 transition metal Inorganic materials 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 7
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methylbenzene Chemical compound CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 150000007514 bases Chemical class 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- DUTKQZIXCWCJHV-UHFFFAOYSA-N (2-methylsulfonyloxyphenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC=C1OS(C)(=O)=O DUTKQZIXCWCJHV-UHFFFAOYSA-N 0.000 description 6
- WYUIWKFIFOJVKW-UHFFFAOYSA-N 1,2-dichloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(Cl)=C1 WYUIWKFIFOJVKW-UHFFFAOYSA-N 0.000 description 6
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper 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
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- 125000005567 fluorenylene group Chemical group 0.000 description 6
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 6
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 6
- 239000005453 ketone based solvent Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- GJQIMXVRFNLMTB-UHFFFAOYSA-N nonyl acetate Chemical compound CCCCCCCCCOC(C)=O GJQIMXVRFNLMTB-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 5
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 5
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
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- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
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- 238000010304 firing Methods 0.000 description 5
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- 229940087646 methanolamine Drugs 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000003002 pH adjusting agent Substances 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
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- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
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- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 4
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 4
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 description 4
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
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- UPZSYVWMIPEBEE-UHFFFAOYSA-N [2-phenyl-4-[9-[3-phenyl-4-(trifluoromethylsulfonyloxy)phenyl]fluoren-9-yl]phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OS(=O)(=O)C(F)(F)F)=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 UPZSYVWMIPEBEE-UHFFFAOYSA-N 0.000 description 1
- GYMHVKIEUGTCBJ-UHFFFAOYSA-N [2-prop-1-enyl-4-[2-[3-prop-1-enyl-4-(trifluoromethylsulfonyloxy)phenyl]propan-2-yl]phenyl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C(C=CC)=CC(C(C)(C)C=2C=C(C=CC)C(OS(=O)(=O)C(F)(F)F)=CC=2)=C1 GYMHVKIEUGTCBJ-UHFFFAOYSA-N 0.000 description 1
- WHMMESYJLGNPBR-UHFFFAOYSA-N [3-(2-bromophenoxy)phenyl]-(2-bromophenyl)methanone Chemical compound BrC1=CC=CC=C1OC1=CC=CC(C(=O)C=2C(=CC=CC=2)Br)=C1 WHMMESYJLGNPBR-UHFFFAOYSA-N 0.000 description 1
- GBBGDHZUZXUMIV-UHFFFAOYSA-N [3-(2-iodophenoxy)phenyl]-(2-iodophenyl)methanone Chemical compound IC1=CC=CC=C1OC1=CC=CC(C(=O)C=2C(=CC=CC=2)I)=C1 GBBGDHZUZXUMIV-UHFFFAOYSA-N 0.000 description 1
- VEYVSCPTDOXIAT-UHFFFAOYSA-N [3-(3-bromophenoxy)phenyl]-(3-bromophenyl)methanone Chemical compound BrC1=CC=CC(OC=2C=C(C=CC=2)C(=O)C=2C=C(Br)C=CC=2)=C1 VEYVSCPTDOXIAT-UHFFFAOYSA-N 0.000 description 1
- UTIQTZUSWYFKAH-UHFFFAOYSA-N [3-(4-bromophenoxy)phenyl]-(4-bromophenyl)methanone Chemical compound C1=CC(Br)=CC=C1OC1=CC=CC(C(=O)C=2C=CC(Br)=CC=2)=C1 UTIQTZUSWYFKAH-UHFFFAOYSA-N 0.000 description 1
- BVQONEUGYLCUFZ-UHFFFAOYSA-N [3-(4-iodophenoxy)phenyl]-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1OC1=CC=CC(C(=O)C=2C=CC(I)=CC=2)=C1 BVQONEUGYLCUFZ-UHFFFAOYSA-N 0.000 description 1
- RYFUALHOSYJMKI-UHFFFAOYSA-N [4-(3,5-difluoro-4-methylsulfonyloxyphenyl)-2,6-difluorophenyl] methanesulfonate Chemical group C1=C(F)C(OS(=O)(=O)C)=C(F)C=C1C1=CC(F)=C(OS(C)(=O)=O)C(F)=C1 RYFUALHOSYJMKI-UHFFFAOYSA-N 0.000 description 1
- ZMVXEPADULICMH-UHFFFAOYSA-N [4-(3-bromophenoxy)phenyl]-(3-bromophenyl)methanone Chemical compound BrC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=C(Br)C=CC=2)=C1 ZMVXEPADULICMH-UHFFFAOYSA-N 0.000 description 1
- HHBRQKFMIFKIEM-UHFFFAOYSA-N [4-(3-iodophenoxy)phenyl]-(3-iodophenyl)methanone Chemical compound IC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=C(I)C=CC=2)=C1 HHBRQKFMIFKIEM-UHFFFAOYSA-N 0.000 description 1
- CAPSSXZCLWWGDD-UHFFFAOYSA-N [4-(4-bromophenoxy)phenyl]-(4-bromophenyl)methanone Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(C(=O)C=2C=CC(Br)=CC=2)C=C1 CAPSSXZCLWWGDD-UHFFFAOYSA-N 0.000 description 1
- BBNDTYMBIMMKFM-UHFFFAOYSA-N [4-(4-iodophenoxy)phenyl]-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1OC1=CC=C(C(=O)C=2C=CC(I)=CC=2)C=C1 BBNDTYMBIMMKFM-UHFFFAOYSA-N 0.000 description 1
- MVYBWGWFGHZGCW-UHFFFAOYSA-N [4-(4-methylsulfonyloxy-3-prop-1-enylphenyl)-2-prop-1-enylphenyl] methanesulfonate Chemical group C1=C(OS(C)(=O)=O)C(C=CC)=CC(C=2C=C(C=CC)C(OS(C)(=O)=O)=CC=2)=C1 MVYBWGWFGHZGCW-UHFFFAOYSA-N 0.000 description 1
- QNHPSMSQYACGQK-UHFFFAOYSA-N [4-(4-methylsulfonyloxyphenyl)phenyl] methanesulfonate Chemical group C1=CC(OS(=O)(=O)C)=CC=C1C1=CC=C(OS(C)(=O)=O)C=C1 QNHPSMSQYACGQK-UHFFFAOYSA-N 0.000 description 1
- ZACXIRGFRIGUMB-UHFFFAOYSA-N [4-[(3,5-difluoro-4-methylsulfonyloxyphenyl)-diphenylmethyl]-2,6-difluorophenyl] methanesulfonate Chemical compound C1=C(F)C(OS(=O)(=O)C)=C(F)C=C1C(C=1C=C(F)C(OS(C)(=O)=O)=C(F)C=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZACXIRGFRIGUMB-UHFFFAOYSA-N 0.000 description 1
- LCJRBTPUBYVATK-UHFFFAOYSA-N [4-[(3,5-dimethyl-4-methylsulfonyloxyphenyl)-diphenylmethyl]-2,6-dimethylphenyl] methanesulfonate Chemical compound CC1=C(OS(C)(=O)=O)C(C)=CC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=C(C)C(OS(C)(=O)=O)=C(C)C=2)=C1 LCJRBTPUBYVATK-UHFFFAOYSA-N 0.000 description 1
- OGPCXXUGJBKMLQ-UHFFFAOYSA-N [4-[(3,5-dimethyl-4-methylsulfonyloxyphenyl)methyl]-2,6-dimethylphenyl] methanesulfonate Chemical compound CC1=C(OS(C)(=O)=O)C(C)=CC(CC=2C=C(C)C(OS(C)(=O)=O)=C(C)C=2)=C1 OGPCXXUGJBKMLQ-UHFFFAOYSA-N 0.000 description 1
- AKOSKCCBUZRJIM-UHFFFAOYSA-N [4-[(4-methylsulfonyloxy-3-prop-1-enylphenyl)-diphenylmethyl]-2-prop-1-enylphenyl] methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C(C=CC)=CC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=C(C=CC)C(OS(C)(=O)=O)=CC=2)=C1 AKOSKCCBUZRJIM-UHFFFAOYSA-N 0.000 description 1
- UVRBDEFLEVJGGK-UHFFFAOYSA-N [4-[(4-methylsulfonyloxyphenyl)-diphenylmethyl]phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C(C=1C=CC(OS(C)(=O)=O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UVRBDEFLEVJGGK-UHFFFAOYSA-N 0.000 description 1
- ZAYUGCIKUUFFLQ-UHFFFAOYSA-N [4-[(4-methylsulfonyloxyphenyl)-phenylmethyl]phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C(C=1C=CC(OS(C)(=O)=O)=CC=1)C1=CC=CC=C1 ZAYUGCIKUUFFLQ-UHFFFAOYSA-N 0.000 description 1
- UOKRNKMVOLSFGZ-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-(3-methyl-4-methylsulfonyloxyphenyl)propan-2-yl]-2-methylphenyl] methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C(C)=CC(C(C=2C=C(C)C(OS(C)(=O)=O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 UOKRNKMVOLSFGZ-UHFFFAOYSA-N 0.000 description 1
- GIXRKJOWRRKHOI-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-(4-methylsulfonyloxy-3-prop-1-enylphenyl)propan-2-yl]-2-prop-1-enylphenyl] methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C(C=CC)=CC(C(C=2C=C(C=CC)C(OS(C)(=O)=O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 GIXRKJOWRRKHOI-UHFFFAOYSA-N 0.000 description 1
- WCLFNEOODLYWBR-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-(4-methylsulfonyloxyphenyl)propan-2-yl]phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(OS(C)(=O)=O)C=C1 WCLFNEOODLYWBR-UHFFFAOYSA-N 0.000 description 1
- CBFKZEAQABANEI-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-[3-methyl-4-(2-methylphenyl)sulfonyloxyphenyl]propan-2-yl]-2-methylphenyl] 2-methylbenzenesulfonate Chemical compound CC1=CC(C(C=2C=C(C)C(OS(=O)(=O)C=3C(=CC=CC=3)C)=CC=2)(C(F)(F)F)C(F)(F)F)=CC=C1OS(=O)(=O)C1=CC=CC=C1C CBFKZEAQABANEI-UHFFFAOYSA-N 0.000 description 1
- YSMXKEMIUZOIOJ-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-[3-methyl-4-(trifluoromethylsulfonyloxy)phenyl]propan-2-yl]-2-methylphenyl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C(C)=CC(C(C=2C=C(C)C(OS(=O)(=O)C(F)(F)F)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 YSMXKEMIUZOIOJ-UHFFFAOYSA-N 0.000 description 1
- AAYJZLQAFBCUET-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-[3-prop-1-enyl-4-(trifluoromethylsulfonyloxy)phenyl]propan-2-yl]-2-prop-1-enylphenyl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C(C=CC)=CC(C(C=2C=C(C=CC)C(OS(=O)(=O)C(F)(F)F)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 AAYJZLQAFBCUET-UHFFFAOYSA-N 0.000 description 1
- SAYPKGSAFXMHRM-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-[4-(2-methylphenyl)sulfonyloxyphenyl]propan-2-yl]phenyl] 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S(=O)(=O)OC1=CC=C(C(C=2C=CC(OS(=O)(=O)C=3C(=CC=CC=3)C)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 SAYPKGSAFXMHRM-UHFFFAOYSA-N 0.000 description 1
- XAQONSRTZUYBTD-UHFFFAOYSA-N [4-[1,1,1,3,3,3-hexafluoro-2-[4-(trifluoromethylsulfonyloxy)phenyl]propan-2-yl]phenyl] trifluoromethanesulfonate Chemical compound C=1C=C(OS(=O)(=O)C(F)(F)F)C=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1 XAQONSRTZUYBTD-UHFFFAOYSA-N 0.000 description 1
- GCLSJKWFIMFMBC-UHFFFAOYSA-N [4-[1-[4-(benzenesulfonyloxy)phenyl]-2,2,2-trifluoro-1-phenylethyl]phenyl] benzenesulfonate Chemical compound C=1C=C(OS(=O)(=O)C=2C=CC=CC=2)C=CC=1C(C=1C=CC(OS(=O)(=O)C=2C=CC=CC=2)=CC=1)(C(F)(F)F)C1=CC=CC=C1 GCLSJKWFIMFMBC-UHFFFAOYSA-N 0.000 description 1
- PZNMFVJCKYRPEJ-UHFFFAOYSA-N [4-[2,2,2-trifluoro-1-(4-methylsulfonyloxyphenyl)-1-phenylethyl]phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C(C(F)(F)F)(C=1C=CC(OS(C)(=O)=O)=CC=1)C1=CC=CC=C1 PZNMFVJCKYRPEJ-UHFFFAOYSA-N 0.000 description 1
- WCWMHNVHZPJPJD-UHFFFAOYSA-N [4-[2,2,2-trifluoro-1-[4-(2-methylphenyl)sulfonyloxyphenyl]-1-phenylethyl]phenyl] 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S(=O)(=O)OC1=CC=C(C(C=2C=CC=CC=2)(C=2C=CC(OS(=O)(=O)C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)C=C1 WCWMHNVHZPJPJD-UHFFFAOYSA-N 0.000 description 1
- XLZFISXQSASZGU-UHFFFAOYSA-N [4-[2,2,2-trifluoro-1-phenyl-1-[4-(trifluoromethylsulfonyloxy)phenyl]ethyl]phenyl] trifluoromethanesulfonate Chemical compound C=1C=C(OS(=O)(=O)C(F)(F)F)C=CC=1C(C=1C=CC(OS(=O)(=O)C(F)(F)F)=CC=1)(C(F)(F)F)C1=CC=CC=C1 XLZFISXQSASZGU-UHFFFAOYSA-N 0.000 description 1
- VOMLLQCELKTJCE-UHFFFAOYSA-N [4-[2-(3,5-difluoro-4-methylsulfonyloxyphenyl)propan-2-yl]-2,6-difluorophenyl] methanesulfonate Chemical compound C=1C(F)=C(OS(C)(=O)=O)C(F)=CC=1C(C)(C)C1=CC(F)=C(OS(C)(=O)=O)C(F)=C1 VOMLLQCELKTJCE-UHFFFAOYSA-N 0.000 description 1
- SMZADXUZZPYJPF-UHFFFAOYSA-N [4-[2-(3,5-dimethyl-4-methylsulfonyloxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dimethylphenyl] methanesulfonate Chemical compound CC1=C(OS(C)(=O)=O)C(C)=CC(C(C=2C=C(C)C(OS(C)(=O)=O)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=C1 SMZADXUZZPYJPF-UHFFFAOYSA-N 0.000 description 1
- VGLBFOOJINWKBI-UHFFFAOYSA-N [4-[2-(3,5-dimethyl-4-methylsulfonyloxyphenyl)propan-2-yl]-2,6-dimethylphenyl] methanesulfonate Chemical compound CC1=C(OS(C)(=O)=O)C(C)=CC(C(C)(C)C=2C=C(C)C(OS(C)(=O)=O)=C(C)C=2)=C1 VGLBFOOJINWKBI-UHFFFAOYSA-N 0.000 description 1
- GCFDWXOOMGOWKR-UHFFFAOYSA-N [4-[2-(3-bromobenzoyl)benzoyl]phenyl]-(3-bromophenyl)methanone Chemical compound BrC1=CC=CC(C(=O)C=2C=CC(=CC=2)C(=O)C=2C(=CC=CC=2)C(=O)C=2C=C(Br)C=CC=2)=C1 GCFDWXOOMGOWKR-UHFFFAOYSA-N 0.000 description 1
- DLLJLGBKPVCXGR-UHFFFAOYSA-N [4-[2-(3-iodobenzoyl)benzoyl]phenyl]-(3-iodophenyl)methanone Chemical compound IC1=CC=CC(C(=O)C=2C=CC(=CC=2)C(=O)C=2C(=CC=CC=2)C(=O)C=2C=C(I)C=CC=2)=C1 DLLJLGBKPVCXGR-UHFFFAOYSA-N 0.000 description 1
- NKQNBLMGBOGQBJ-UHFFFAOYSA-N [4-[2-(4-bromobenzoyl)benzoyl]phenyl]-(4-bromophenyl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=C(C(=O)C=2C(=CC=CC=2)C(=O)C=2C=CC(Br)=CC=2)C=C1 NKQNBLMGBOGQBJ-UHFFFAOYSA-N 0.000 description 1
- YUUHVATVCSWJFS-UHFFFAOYSA-N [4-[2-(4-iodobenzoyl)benzoyl]phenyl]-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1C(=O)C1=CC=C(C(=O)C=2C(=CC=CC=2)C(=O)C=2C=CC(I)=CC=2)C=C1 YUUHVATVCSWJFS-UHFFFAOYSA-N 0.000 description 1
- QMNKLUMCNRYXFL-UHFFFAOYSA-N [4-[2-(4-methylsulfonyloxy-3-prop-1-enylphenyl)propan-2-yl]-2-prop-1-enylphenyl] methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C(C=CC)=CC(C(C)(C)C=2C=C(C=CC)C(OS(C)(=O)=O)=CC=2)=C1 QMNKLUMCNRYXFL-UHFFFAOYSA-N 0.000 description 1
- HKTHUQUSMNQOQO-UHFFFAOYSA-N [4-[2-(4-methylsulfonyloxyphenyl)propan-2-yl]phenyl] methanesulfonate Chemical compound C=1C=C(OS(C)(=O)=O)C=CC=1C(C)(C)C1=CC=C(OS(C)(=O)=O)C=C1 HKTHUQUSMNQOQO-UHFFFAOYSA-N 0.000 description 1
- KKPRQNYAJORHNT-UHFFFAOYSA-N [4-[2-[3,5-dimethyl-4-(2-methylphenyl)sulfonyloxyphenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dimethylphenyl] 2-methylbenzenesulfonate Chemical compound CC1=CC(C(C=2C=C(C)C(OS(=O)(=O)C=3C(=CC=CC=3)C)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=CC(C)=C1OS(=O)(=O)C1=CC=CC=C1C KKPRQNYAJORHNT-UHFFFAOYSA-N 0.000 description 1
- GGMYJQKELGHDCC-UHFFFAOYSA-N [4-[2-[3,5-dimethyl-4-(trifluoromethylsulfonyloxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dimethylphenyl] trifluoromethanesulfonate Chemical compound CC1=C(OS(=O)(=O)C(F)(F)F)C(C)=CC(C(C=2C=C(C)C(OS(=O)(=O)C(F)(F)F)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=C1 GGMYJQKELGHDCC-UHFFFAOYSA-N 0.000 description 1
- HZFAHQZNHPEDTG-UHFFFAOYSA-N [4-[2-[4-(2-methylphenyl)sulfonyloxyphenyl]propan-2-yl]phenyl] 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S(=O)(=O)OC1=CC=C(C(C)(C)C=2C=CC(OS(=O)(=O)C=3C(=CC=CC=3)C)=CC=2)C=C1 HZFAHQZNHPEDTG-UHFFFAOYSA-N 0.000 description 1
- BEUWBKDUFJXWCO-UHFFFAOYSA-N [4-[2-[4-(benzenesulfonyloxy)-3,5-dimethylphenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dimethylphenyl] benzenesulfonate Chemical compound CC1=CC(C(C=2C=C(C)C(OS(=O)(=O)C=3C=CC=CC=3)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=CC(C)=C1OS(=O)(=O)C1=CC=CC=C1 BEUWBKDUFJXWCO-UHFFFAOYSA-N 0.000 description 1
- GUCXVGJPYSPBNE-UHFFFAOYSA-N [4-[2-[4-(benzenesulfonyloxy)-3,5-dimethylphenyl]propan-2-yl]-2,6-dimethylphenyl] benzenesulfonate Chemical compound CC1=CC(C(C)(C)C=2C=C(C)C(OS(=O)(=O)C=3C=CC=CC=3)=C(C)C=2)=CC(C)=C1OS(=O)(=O)C1=CC=CC=C1 GUCXVGJPYSPBNE-UHFFFAOYSA-N 0.000 description 1
- MLKXWOWJUBZKPD-UHFFFAOYSA-N [4-[2-[4-(benzenesulfonyloxy)-3-methylphenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-methylphenyl] benzenesulfonate Chemical compound CC1=CC(C(C=2C=C(C)C(OS(=O)(=O)C=3C=CC=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)=CC=C1OS(=O)(=O)C1=CC=CC=C1 MLKXWOWJUBZKPD-UHFFFAOYSA-N 0.000 description 1
- VPFSITOPMFIWLH-UHFFFAOYSA-N [4-[2-[4-(benzenesulfonyloxy)-3-methylphenyl]propan-2-yl]-2-methylphenyl] benzenesulfonate Chemical compound CC1=CC(C(C)(C)C=2C=C(C)C(OS(=O)(=O)C=3C=CC=CC=3)=CC=2)=CC=C1OS(=O)(=O)C1=CC=CC=C1 VPFSITOPMFIWLH-UHFFFAOYSA-N 0.000 description 1
- CFLLNKSKBGAZAA-UHFFFAOYSA-N [4-[2-[4-(benzenesulfonyloxy)-3-prop-1-enylphenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-prop-1-enylphenyl] benzenesulfonate Chemical compound CC=CC1=CC(C(C=2C=C(C=CC)C(OS(=O)(=O)C=3C=CC=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)=CC=C1OS(=O)(=O)C1=CC=CC=C1 CFLLNKSKBGAZAA-UHFFFAOYSA-N 0.000 description 1
- RPNDFLKGIZXTOA-UHFFFAOYSA-N [4-[2-[4-(benzenesulfonyloxy)-3-prop-1-enylphenyl]propan-2-yl]-2-prop-1-enylphenyl] benzenesulfonate Chemical compound CC=CC1=CC(C(C)(C)C=2C=C(C=CC)C(OS(=O)(=O)C=3C=CC=CC=3)=CC=2)=CC=C1OS(=O)(=O)C1=CC=CC=C1 RPNDFLKGIZXTOA-UHFFFAOYSA-N 0.000 description 1
- FZFIHDLUPFIRGR-UHFFFAOYSA-N [4-[2-[4-(benzenesulfonyloxy)phenyl]propan-2-yl]phenyl] benzenesulfonate Chemical compound C=1C=C(OS(=O)(=O)C=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OS(=O)(=O)C1=CC=CC=C1 FZFIHDLUPFIRGR-UHFFFAOYSA-N 0.000 description 1
- JBZAWUXTXDAWOT-UHFFFAOYSA-N [4-[2-[4-(trifluoromethylsulfonyloxy)phenyl]propan-2-yl]phenyl] trifluoromethanesulfonate Chemical compound C=1C=C(OS(=O)(=O)C(F)(F)F)C=CC=1C(C)(C)C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1 JBZAWUXTXDAWOT-UHFFFAOYSA-N 0.000 description 1
- MIGBFJPJWLFPBT-UHFFFAOYSA-N [4-[9-(3,5-difluoro-4-methylsulfonyloxyphenyl)fluoren-9-yl]-2,6-difluorophenyl] methanesulfonate Chemical compound C1=C(F)C(OS(=O)(=O)C)=C(F)C=C1C1(C=2C=C(F)C(OS(C)(=O)=O)=C(F)C=2)C2=CC=CC=C2C2=CC=CC=C21 MIGBFJPJWLFPBT-UHFFFAOYSA-N 0.000 description 1
- QLSXGFCWNYDSHQ-UHFFFAOYSA-N [4-[9-(3,5-dimethyl-4-methylsulfonyloxyphenyl)fluoren-9-yl]-2,6-dimethylphenyl] methanesulfonate Chemical compound CC1=C(OS(C)(=O)=O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(OS(C)(=O)=O)=C(C)C=2)=C1 QLSXGFCWNYDSHQ-UHFFFAOYSA-N 0.000 description 1
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- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- IXJNGXCZSCHDFE-UHFFFAOYSA-N triphenoxy(phenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 IXJNGXCZSCHDFE-UHFFFAOYSA-N 0.000 description 1
- FNNJGIKXHZZGCV-UHFFFAOYSA-N triphenoxy(propan-2-yl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C(C)C)OC1=CC=CC=C1 FNNJGIKXHZZGCV-UHFFFAOYSA-N 0.000 description 1
- AMUIJRKZTXWCEA-UHFFFAOYSA-N triphenoxy(propyl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCC)OC1=CC=CC=C1 AMUIJRKZTXWCEA-UHFFFAOYSA-N 0.000 description 1
- MUCRQDBOUNQJFE-UHFFFAOYSA-N triphenoxy(triphenoxysilyl)silane Chemical compound C=1C=CC=CC=1O[Si]([Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 MUCRQDBOUNQJFE-UHFFFAOYSA-N 0.000 description 1
- QDOHRQCMIFOPEY-UHFFFAOYSA-N tripropoxy(2-tripropoxysilylethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CC[Si](OCCC)(OCCC)OCCC QDOHRQCMIFOPEY-UHFFFAOYSA-N 0.000 description 1
- NBAPKCYEEBMZDW-UHFFFAOYSA-N tripropoxy-(2-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1[Si](OCCC)(OCCC)OCCC NBAPKCYEEBMZDW-UHFFFAOYSA-N 0.000 description 1
- YMAKWPVRMIUZBP-UHFFFAOYSA-N tripropoxy-(3-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC([Si](OCCC)(OCCC)OCCC)=C1 YMAKWPVRMIUZBP-UHFFFAOYSA-N 0.000 description 1
- FOUOZDXPXSKVEL-UHFFFAOYSA-N tripropoxy-(4-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=C([Si](OCCC)(OCCC)OCCC)C=C1 FOUOZDXPXSKVEL-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GBGOZMPAPWGNGR-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]ethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)CC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C GBGOZMPAPWGNGR-UHFFFAOYSA-N 0.000 description 1
- ZZEMYLNHCSTIPH-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C ZZEMYLNHCSTIPH-UHFFFAOYSA-N 0.000 description 1
- NNKMRNUOGTXRCM-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[3-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC([Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)=C1 NNKMRNUOGTXRCM-UHFFFAOYSA-N 0.000 description 1
- PITXUFPLSLHXRV-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[4-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=C([Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)C=C1 PITXUFPLSLHXRV-UHFFFAOYSA-N 0.000 description 1
- QJJZQRNPNLTSNS-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[tris[(2-methylpropan-2-yl)oxy]silylmethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C QJJZQRNPNLTSNS-UHFFFAOYSA-N 0.000 description 1
- KGOOITCIBGXHJO-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-phenylsilane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1 KGOOITCIBGXHJO-UHFFFAOYSA-N 0.000 description 1
- MJIHPVLPZKWFBL-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propan-2-ylsilane Chemical compound CC(C)(C)O[Si](C(C)C)(OC(C)(C)C)OC(C)(C)C MJIHPVLPZKWFBL-UHFFFAOYSA-N 0.000 description 1
- DIZPPYBTFPZSGK-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C DIZPPYBTFPZSGK-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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Abstract
폴리실록산계 절연막의 낮은 비유전율을 유지하면서, 듀얼 다마신 구조 형성시 RIE 등의 처리에 내성을 갖는 절연막의 형성 방법을 제공한다.
기재 상에 실란 화합물을 가수분해 축합시켜 폴리실록산계 절연막을 형성한다. 이어서, 상기 폴리실록산계 절연막 상에, 하기 화학식으로 표시되는 폴리카르보실란 화합물을 용매에 용해시킴으로써 얻어진 용액을 도포하고, 도막을 가열하여 폴리카르보실란계 절연막을 형성한다.
이어서, 상기 폴리카르보실란계 절연막 상에 유기계 절연막을 형성한다.
실란 화합물, 폴리실록산계 절연막, 폴리카르보실란계 절연막, 유기계 절연막, 막 형성용 조성물
Description
본 발명은 절연막의 형성 방법에 관한 것이고, 더욱 상세하게는 반도체 소자에서의 층간 절연막 등에 바람직하게 사용할 수 있는 절연막 및 그의 형성 방법, 및 막 형성용 조성물에 관한 것이다.
종래, 반도체 소자 등에서의 층간 절연막으로서, CVD(화학적 증착)법 등의 진공 공정에 의해 형성된 실리카(Si02)막이 많이 이용되었다. 또한, 최근에는 보다 균일한 막 두께를 갖는 층간 절연막을 형성하는 것을 목적으로, SOG(스핀 온 글래스(Spin on Glass))막이라 불리는 테트라알콕시실란의 가수분해 생성물을 주성분으로 하는 도포형 절연막도 사용되고 있다. 또한, 반도체 소자 등의 고집적화에 따른 유기 SOG라 불리는 폴리오르가노실록산을 주성분으로 하는 비유전율(比誘電率)이 낮은 층간 절연막도 개발되고 있다.
또한, 반도체 소자 등이 한층 더 고집적화 또는 다층화됨에 따라서, 보다 우수한 도체간 전기 절연성이 요구되고 있고, 따라서 보존 안정성이 양호하고, 비유전율이 보다 낮고(Low-k), 또한 누설 전류 특성이 우수한 층간 절연막이 요구되고 있다.
그런데, 반도체 장치의 배선층의 형성에 있어서, 듀얼 다마신(dual damascene) 구조를 갖는 배선의 경우, 비아(via)를 형성하는 층으로서 폴리실록산계 절연막으로 대표되는 Low-k 절연막을 형성하고, 트렌치(trench)를 형성하는 층으로서 동일하게 Low-k 절연막인 유기계 절연막을 형성하는 경우가 있다. 유기계 절연막에 트렌치를 형성하는 경우, 암모니아나 H2/N2 등의 가스를 이용하여 리액티브 이온 에칭(Reactive Ion Etching, RIE)이 수행되는데, 이때 아래쪽에 형성되어 있는 폴리실록산계 절연막에 에칭에 의한 손상이 발생하는 경우가 있다. 이러한 손상이 절연막에 발생하면, 절연막의 비유전율이 상승하거나, 에칭, 애싱(ashing) 또는 습식 세정 등의 공정에 대한 절연막의 내성이 저하되는 문제가 생긴다. 이는 배선의 특성을 저하시켜 반도체 장치의 신뢰성을 손상시킨다.
본 발명의 목적은, 고집적화 및 다층화가 요망되고 있는 반도체 소자 등에서 바람직하게 사용할 수 있고, 비유전율이 낮으며 에칭, 애싱 또는 습식 세정 등의 공정에 대한 내성 등도 우수한 절연막을 형성할 수 있는 형성 방법 및 절연막을 제공하는 것에 있다.
본 발명의 다른 목적은, 이러한 절연막의 형성 방법에 바람직하게 사용할 수 있는 막 형성용 조성물을 제공하는 것에 있다.
본 발명에 따른 절연막의 형성 방법은,
기재 상에 폴리실록산계 절연막을 형성하는 공정,
상기 폴리실록산계 절연막 상에 폴리카르보실란계 절연막을 형성하는 공정, 및
상기 폴리카르보실란계 절연막 상에 유기계 절연막을 형성하는 공정
을 포함하는 절연막의 형성 방법이며,
상기 폴리실록산계 절연막은, 하기 화학식 1 내지 3으로 표시되는 화합물의 군에서 선택된 1종 이상의 실란 화합물을 가수분해 축합시킴으로써 형성되고,
상기 폴리카르보실란계 절연막은, 하기 화학식 4로 표시되는 폴리카르보실란 화합물을 용매에 용해시킴으로써 얻어진 용액을 도포한 후, 도막을 가열함으로써 형성된다.
식 중, R은 수소 원자, 불소 원자 또는 유기기를 나타내고, R1은 유기기를 나타내고, a는 1 또는 2의 정수를 나타내고;
R2는 유기기를 나타내고;
R3 내지 R6은 동일하거나 상이하며, 각각 유기기를 나타내고, b 및 c는 동일하거나 상이하며, 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)m-으로 표시되는 기(여기서, m은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타내고;
R8 내지 R11은 동일하거나 상이하며, 수소 원자, 할로겐 원자, 히드록실기, 알콕실기, 술폰기, 메탄술폰기, 트리플루오로메탄술폰기 또는 유기기를 나타내고, R12 내지 R14는 동일하거나 상이하며, 치환 또는 비치환의 알킬렌기, 알케닐기, 알키닐기 또는 아릴렌기를 나타내고, x, y 및 z는 0 내지 10,000의 정수이며, 10<x+y+z<20,000의 조건을 만족시킨다.
본 발명에 따른 절연막은,
기재 상에 형성된 폴리실록산계 절연막,
상기 폴리실록산계 절연막 상에 형성된 폴리카르보실란계 절연막, 및
상기 폴리카르보실란계 절연막 상에 형성된 유기계 절연막
을 포함하는 절연막이며,
상기 폴리실록산계 절연막은, 하기 화학식 1 내지 3으로 표시되는 화합물의 군에서 선택된 1종 이상의 실란 화합물을 가수분해 축합시킴으로써 형성되고,
상기 폴리카르보실란계 절연막은, 하기 화학식 4로 표시되는 폴리카르보실란 화합물을 용매에 용해시킴으로써 얻어진 용액을 도포한 후, 도막을 가열함으로써 형성된다.
<화학식 1>
RaSi(OR1)4-a
<화학식 2>
Si(OR2)4
<화학식 3>
R3 b(R4O)3- bSi-(R7)d-Si(OR5)3- cR6 c
<화학식 4>
식 중, R은 수소 원자, 불소 원자 또는 유기기를 나타내고, R1은 유기기를 나타내고, a는 1 또는 2의 정수를 나타내고;
R2는 유기기를 나타내고;
R3 내지 R6은 동일하거나 상이하며, 각각 유기기를 나타내고, b 및 c는 동일하거나 상이하며, 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)m-으로 표시되는 기(여기서, m은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타내고;
R8 내지 R11은 동일하거나 상이하며, 수소 원자, 할로겐 원자, 히드록실기, 알콕실기, 술폰기, 메탄술폰기, 트리플루오로메탄술폰기 또는 유기기를 나타내고, R12 내지 R14는 동일하거나 상이하며, 치환 또는 비치환의 알킬렌기, 알케닐기, 알키닐기 또는 아릴렌기를 나타내고, x, y 및 z는 0 내지 10,000의 정수이며, 10<x+y+z<20,000의 조건을 만족시킨다.
본 발명에 따른 조성물은 본 발명의 절연막의 형성 방법에 이용되는 폴리카르보실란계 절연막을 위한 막 형성용 조성물이며,
하기 화학식 4로 표시되는 폴리카르보실란 화합물을 용매에 용해시킨 용액을 포함한다.
<화학식 4>
식 중, R8 내지 R11은 동일하거나 상이하며, 수소 원자, 할로겐 원자, 히드록실기, 알콕실기, 술폰기, 메탄술폰기, 트리플루오로메탄술폰기 또는 유기기를 나타내고, R12 내지 R14는 동일하거나 상이하며, 치환 또는 비치환의 알킬렌기, 알케닐기, 알키닐기 또는 아릴렌기를 나타내고, x, y 및 z는 0 내지 10,000의 정수이며, 10<x+y+z<20,000의 조건을 만족시킨다.
본 발명에 따른 절연막의 형성 방법에 따르면, 소위 Low-k막인 폴리실록산계 절연막을 형성한 후에 폴리카르보실란계 절연막을 형성함으로써, 유기계 절연막의 RIE시 에칭의 영향이 폴리실록산계 절연막에 직접적으로 미치지 않아, 폴리실록산계 절연막이 손상을 입지 않는다. 폴리실록산계 절연막과 유기계 절연막 사이에 삽입되는 폴리카르보실란계 절연막의 경우, 플라즈마에 노출되더라도 손상되기 어렵고, 절연성이나 기계적 강도 등이 영향을 받기 어렵다.
따라서, 본 발명에 따른 절연막의 형성 방법에 따르면, 폴리실록산계 절연막의 낮은 비유전율을 유지하면서, 예를 들면 듀얼 다마신 구조를 형성할 때 RIE 등의 처리에 대해 내성을 갖는 절연막을 형성할 수 있다. 그 결과, 신뢰성이 높은 배선층을 형성할 수 있다. 본 발명의 절연막은 폴리실록산계 절연막, 폴리카르보 실란계 절연막 및 유기계 절연막을 포함할 수 있고, 또한 이들 이외의 절연막도 가질 수 있다.
본 발명의 절연막은 상술한 바와 같이, 비유전율이 낮으며 공정 내성이 우수하기 때문에, 예를 들면 반도체 소자의 층간 절연막으로서 바람직하게 사용할 수 있다. 특히, 듀얼 다마신 구조를 갖는 배선층의 형성에도 바람직하게 사용할 수 있다.
이하에, 본 발명의 절연막의 형성 방법, 절연막 및 막 형성용 조성물에 대하여 더욱 상세히 설명한다.
본 발명에 따른 절연막의 형성 방법은, 기재 상에 폴리실록산계 절연막을 형성하는 공정, 상기 폴리실록산계 절연막 상에 폴리카르보실란계 절연막을 형성하는 공정, 및 상기 폴리카르보실란계 절연막 상에 유기계 절연막을 형성하는 공정을 포함한다. 또한, 본 발명에 있어서 「도막」이란, 막 형성용 조성물을 기재 상에 도포하고, 유기 용매를 제거함으로써 형성되는 막을 말한다.
1. 폴리실록산계 절연막의 형성 방법
1.1. 폴리실록산계 절연막을 형성하기 위한 성분((A) 성분)
본 발명의 절연막의 형성 방법에 있어서, (A) 성분이란, 하기 화학식 1로 표시되는 화합물(이하, 「화합물 1」이라 함), 하기 화학식 2로 표시되는 화합물(이하, 「화합물 2」라 함) 및 하기 화학식 3으로 표시되는 화합물(이하, 「화합물 3」이라 함)의 군에서 선택된 1종 이상의 실란 화합물을 가수분해 축합시킴으로써 얻어지는 폴리실록산 화합물이다. 또한, 이하의 설명에 있어서, (A) 성분이라 할 때, 상기 폴리실록산 화합물이 유기 용매에 용해 또는 분산되어 있는 경우도 포함되는 것으로 한다.
<화학식 1>
RaSi(OR1)4-a
<화학식 2>
Si(OR2)4
<화학식 3>
R3 b(R4O)3- bSi-(R7)d-Si(OR5)3- cR6 c
식 중, R은 수소 원자, 불소 원자 또는 유기기를 나타내고, R1은 유기기를 나타내고, a는 1 또는 2의 정수를 나타내고;
R2는 유기기를 나타내고;
R3 내지 R6은 동일하거나 상이하며, 각각 유기기를 나타내고, b 및 c는 동일하거나 상이하며, 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)m-으로 표시되는 기(여기서, m은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
1.1.1. 화합물 1
상기 화학식 1 중, R과 R1로 표시되는 유기기로는 알킬기, 아릴기, 알릴기, 글리시딜기 등을 들 수 있다. 그 중에서도, 화학식 1 중, R1의 유기기는 특히, 알킬기 또는 페닐기인 것이 바람직하다. 여기서, 알킬기로는, 메틸기, 에틸기, 프로필기, 부틸기 등을 들 수 있고, 바람직하게는 탄소수 1 내지 5이고, 쇄상 또는 분지상일 수 있으며, 또한 수소 원자가 불소 원자 등으로 치환될 수도 있다. 상기 화학식 1의 아릴기로는, 페닐기, 나프틸기, 메틸페닐기, 에틸페닐기, 클로로페닐기, 브로모페닐기, 플루오로페닐기 등을 들 수 있다.
화합물 1의 구체예로는, 메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리이소프로폭시실란, 메틸트리-n-부톡시실란, 메틸트리-sec-부톡시실란, 메틸트리-tert-부톡시실란, 메틸트리페녹시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 에틸트리-n-프로폭시실란, 에틸트리이소프로폭시실란, 에틸트리-n-부톡시실란, 에틸트리-sec-부톡시실란, 에틸트리-tert-부톡시실란, 에틸트리페녹시실란, n-프로필트리메톡시실란, n-프로필트리에톡시실란, n-프로필트리-n-프로폭시실란, n-프로필트리이소프로폭시실란, n-프로필트리-n-부톡시실란, n-프로필트리-sec-부톡시실란, n-프로필트리-tert-부톡시실란, n-프로필트리페녹시실란, 이소프로필트리메톡시실란, 이소프로필트리에톡시실란, 이소프로필트리-n-프로폭시실란, 이소프로필트리이소프로폭시실란, 이소프로필트리-n-부톡시실란, 이소프로필트리-sec-부톡시실란, 이소프로필트리-tert-부톡시실란, 이소프로필트리페녹시실란, n-부틸트리메톡시실란, n-부틸트리에톡시실란, n-부틸트리-n-프로폭시실 란, n-부틸트리이소프로폭시실란, n-부틸트리-n-부톡시실란, n-부틸트리-sec-부톡시실란, n-부틸트리-tert-부톡시실란, n-부틸트리페녹시실란, sec-부틸트리메톡시실란, sec-부틸이소트리에톡시실란, sec-부틸트리-n-프로폭시실란, sec-부틸트리이소프로폭시실란, sec-부틸트리-n-부톡시실란, sec-부틸트리-sec-부톡시실란, sec-부틸트리-tert-부톡시실란, sec-부틸트리페녹시실란, tert-부틸트리메톡시실란, tert-부틸트리에톡시실란, tert-부틸트리-n-프로폭시실란, tert-부틸트리이소프로폭시실란, tert-부틸트리-n-부톡시실란, tert-부틸트리-sec-부톡시실란, tert-부틸트리-tert-부톡시실란, tert-부틸트리페녹시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 페닐트리-n-프로폭시실란, 페닐트리이소프로폭시실란, 페닐트리-n-부톡시시라디, 페닐트리-sec-부톡시실란, 페닐트리-tert-부톡시실란, 페닐트리페녹시실란, 디메틸디메톡시실란, 디메틸디에톡시실란, 디메틸디-n-프로폭시실란, 디메틸디이소프로폭시실란, 디메틸디-n-부톡시실란, 디메틸디-sec-부톡시실란, 디메틸디-tert-부톡시실란, 디메틸디페녹시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디에틸디-n-프로폭시실란, 디에틸디이소프로폭시실란, 디에틸디-n-부톡시실란, 디에틸디-sec-부톡시실란, 디에틸디-tert-부톡시실란, 디에틸디페녹시실란, 디-n-프로필디메톡시실란, 디-n-프로필디에톡시실란, 디-n-프로필디-n-프로폭시실란, 디-n-프로필디이소프로폭시실란, 디-n-프로필디-n-부톡시실란, 디-n-프로필디-sec-부톡시실란, 디-n-프로필디-tert-부톡시실란, 디-n-프로필디페녹시실란, 디이소프로필디메톡시실란, 디이소프로필디에톡시실란, 디이소프로필디-n-프로폭시실란, 디이소프로필디이소프로폭시실란, 디이소프로필디-n-부톡시실란, 디이소프로필디-sec- 부톡시실란, 디이소프로필디-tert-부톡시실란, 디이소프로필디페녹시실란, 디-n-부틸디메톡시실란, 디-n-부틸디에톡시실란, 디-n-부틸디-n-프로폭시실란, 디-n-부틸디이소프로폭시실란, 디-n-부틸디-n-부톡시실란, 디-n-부틸디-sec-부톡시실란, 디-n-부틸디-tert-부톡시실란, 디-n-부틸디페녹시실란, 디-sec-부틸디메톡시실란, 디-sec-부틸디에톡시실란, 디-sec-부틸디-n-프로폭시실란, 디-sec-부틸디이소프로폭시실란, 디-sec-부틸디-n-부톡시실란, 디-sec-부틸디-sec-부톡시실란, 디-sec-부틸디-tert-부톡시실란, 디-sec-부틸디페녹시실란, 디-tert-부틸디메톡시실란, 디-tert-부틸디에톡시실란, 디-tert-부틸디-n-프로폭시실란, 디-tert-부틸디이소프로폭시실란, 디-tert-부틸디-n-부톡시실란, 디-tert-부틸디-sec-부톡시실란, 디-tert-부틸디-tert-부톡시실란, 디-tert-부틸디페녹시실란, 디페닐디메톡시실란, 디페닐디-에톡시실란, 디페닐디-n-프로폭시실란, 디페닐디이소프로폭시실란, 디페닐디-n-부톡시실란, 디페닐디-sec-부톡시실란, 디페닐디-tert-부톡시실란, 디페닐디페녹시실란, 디비닐디메톡시실란, γ-아미노프로필디메톡시실란, γ-아미노프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란, γ-글리시독시프로필트리에톡시실란, γ-트리플루오로프로필트리메톡시실란, γ-트리플루오로프로필트리에톡시실란을 들 수 있다. 이들은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
화합물 I로서 특히 바람직한 화합물은 메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-iso-프로폭시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 디메틸디메톡시실란, 디메틸디에톡시실란, 디에틸디메톡 시실란, 디에틸디에톡시실란, 디페닐디메톡시실란, 디페닐디에톡시실란, 테트라메톡시실란, 테트라메톡시실란, 테트라에톡시실란, 테트라-n-프로폭시실란, 테트라-iso-프로폭시실란, 테트라-n-부톡실란, 테트라-sec-부톡시실란, 테트라-tert-부톡시실란, 테트라페녹시실란 등이다.
1.1.2. 화합물 2
화학식 2의 R2의 유기기로는, 상기 화학식 1에서 예시한 것와 동일한 기를 들 수 있다.
화합물 2의 구체예로는, 테트라메톡시실란, 테트라에톡시실란, 테트라-n-프로폭시실란, 테트라-iso-프로폭시실란, 테트라-n-부톡시실란, 테트라-sec-부톡시실란, 테트라-tert-부톡시실란, 테트라페녹시실란 등을 들 수 있고, 특히 바람직한 화합물로는 테트라메톡시실란, 테트라에톡시실란을 들 수 있다. 이들은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
1.1.3. 화합물 3
화학식 3에서, d=0인 화합물로는, 헥사메톡시디실란, 헥사에톡시디실란, 헥사페녹시디실란, 1,1,1,2,2-펜타메톡시-2-메틸디실란, 1,1,1,2,2-펜타에톡시-2-메틸디실란, 1,1,1,2,2-펜타페녹시-2-메틸디실란, 1,1,1,2,2-펜타메톡시-2-에틸디실란, 1,1,1,2,2-펜타에톡시-2-에틸디실란, 1,1,1,2,2-펜타페녹시-2-에틸디실란, 1,1,1,2,2-펜타메톡시-2-페닐디실란, 1,1,1,2,2-펜타에톡시-2-페닐디실란, 1,1,1,2,2-펜타페녹시-2-페닐디실란, 1,1,2,2-테트라메톡시-1,2-디메틸디실란, 1,1,2,2-테트라에톡시-1,2-디메틸디실란, 1,1,2,2-테트라페녹시-1,2-디메틸디실란, 1,1,2,2-테트라메톡시-1,2-디에틸디디런, 1,1,1,2,2-테트라에톡시-1,2-디에틸디실란, 1,1,2,2-테트라페녹시-1,2-디에틸디실란, 1,1,2,2-테트라메톡시-1,2-디페닐디실란, 1,1,2,2-테트라에톡시-1,2-디페닐디실란, 1,1,2,2-테트라페녹시-1,2-디페닐디실란, 1,1,2-트리메톡시-1,2,2-트리메틸디실란, 1,1,2-트리에톡시-1,2,2-트리메틸디실란, 1,1,2-트리페녹시-1,2,2-트리메틸디실란, 1,1,2-트리메톡시-1,2,2-트리에틸디실란, 1,1,2-트리에톡시-1,2,2-트리에틸디실란, 1,1,2-트리페녹시-1,2,2-트리에틸디실란, 1,1,2-트리메톡시-1,2,2-트리페닐디실란, 1,1,2-트리에톡시-1,2,2-트리페닐디실란, 1,1,2-트리페녹시-1,2,2-트리페닐디실란, 1,2-디메톡시-1,1,2,2-테트라메틸디실란, 1,2-디에톡시-1,1,2,2-테트라메틸디실란, 1,2-디페녹시-1,1,2,2-테트라메틸디실란, 1,2-디메톡시-1,1,2,2-테트라에틸디실란, 1,2-디에톡시-1,1,2,2-테트라에틸디실란, 1,2-디페녹시-1,1,2,2-테트라에틸디실란, 1,2-디메톡시-1,1,2,2-테트라페닐디실란, 1,2-디에톡시-1,1,2,2-테트라페닐디실란, 1,2-디페녹시-1,1,2,2-테트라페닐디실란 등을 들 수 있다.
이들 중, 헥사메톡시디실란, 헥사에톡시디실란, 1,1,2,2-테트라메톡시-1,2-디메틸디실란, 1,1,2,2-테트라에톡시-1,2-디메틸디실란, 1,1,2,2-테트라메톡시-1,2-디페닐디실란, 1,2-디메톡시-1,1,2,2-테트라메틸디실란, 1,2-디에톡시-1,1,2,2-테트라메틸디실란, 1,2-디메톡시-1,1,2,2-테트라페닐디실란, 1,2-디에톡시-1,1,2,2-테트라페닐디실란 등을 바람직한 예로서 들 수 있다.
또한, 화학식 3 중, R7이 -(CH2)m-으로 표시되는 기인 화합물로는, 비스(트리메톡시실릴)메탄, 비스(트리에톡시실릴)메탄, 비스(트리-n-프로폭시실릴)메탄, 비스(트리-iso-프로폭시실릴)메탄, 비스(트리-n-부톡시실릴)메탄, 비스(트리-sec-부톡시실릴)메탄, 비스(트리-tert-부톡시실릴)메탄, 1,2-비스(트리메톡시실릴)에탄, 1,2-비스(트리에톡시실릴)에탄, 1,2-비스(트리-n-프로폭시실릴)에탄, 1,2-비스(트리-iso-프로폭시실릴)에탄, 1,2-비스(트리-n-부톡시실릴)에탄, 1,2-비스(트리-sec-부톡시실릴)에탄, 1,2-비스(트리-tert-부톡시실릴)에탄, 1-(디메톡시메틸실릴)-1-(트리메톡시실릴)메탄, 1-(디에톡시메틸실릴)-1-(트리에톡시실릴)메탄, 1-(디-n-프로폭시메틸실릴)-1-(트리-n-프로폭시실릴)메탄, 1-(디-iso-프로폭시메틸실릴)-1-(트리-iso-프로폭시실릴)메탄, 1-(디-n-부톡시메틸실릴)-1-(트리-n-부톡시실릴)메탄, 1-(디-sec-부톡시메틸실릴)-1-(트리-sec-부톡시실릴)메탄, 1-(디-tert-부톡시메틸실릴)-1-(트리-tert-부톡시실릴)메탄, 1-(디메톡시메틸실릴)-2-(트리메톡시실릴)에탄, 1-(디에톡시메틸실릴)-2-(트리에톡시실릴)에탄, 1-(디-n-프로폭시메틸실릴)-2-(트리-n-프로폭시실릴)에탄, 1-(디-iso-프로폭시메틸실릴)-2-(트리-iso-프로폭시실릴)에탄, 1-(디-n-부톡시메틸실릴)-2-(트리-n-부톡시실릴)에탄, 1-(디-sec-부톡시메틸실릴)-2-(트리-sec-부톡시실릴)에탄, 1-(디-tert-부톡시메틸실릴)-2-(트리-tert-부톡시실릴)에탄, 비스(디메톡시메틸실릴)메탄, 비스(디에톡시메틸실릴)메탄, 비스(디-n-프로폭시메틸실릴)메탄, 비스(디-iso-프로폭시메틸실릴)메탄, 비스(디-n-부톡시메틸실릴)메탄, 비스(디-sec-부톡시메틸실릴)메탄, 비스(디-tert-부톡 시메틸실릴)메탄, 1,2-비스(디메톡시메틸실릴)에탄, 1,2-비스(디에톡시메틸실릴)에탄, 1,2-비스(디-n-프로폭시메틸실릴)에탄, 1,2-비스(디-iso-프로폭시메틸실릴)에탄, 1,2-비스(디-n-부톡시메틸실릴)에탄, 1,2-비스(디-sec-부톡시메틸실릴)에탄 및 1,2-비스(디-tert-부톡시메틸실릴)에탄, 1,2-비스(트리메톡시실릴)벤젠, 1,2-비스(트리에톡시실릴)벤젠, 1,2-비스(트리-n-프로폭시실릴)벤젠, 1,2-비스(트리-iso-프로폭시실릴)벤젠, 1,2-비스(트리-n-부톡시실릴)벤젠, 1,2-비스(트리-sec-부톡시실릴)벤젠, 1,2-비스(트리-tert-부톡시실릴)벤젠, 1,3-비스(트리메톡시실릴)벤젠, 1,3-비스(트리에톡시실릴)벤젠, 1,3-비스(트리-n-프로폭시실릴)벤젠, 1,3-비스(트리-iso-프로폭시실릴)벤젠, 1,3-비스(트리-n-부톡시실릴)벤젠, 1,3-비스(트리-sec-부톡시실릴)벤젠, 1,3-비스(트리-tert-부톡시실릴)벤젠, 1,4-비스(트리메톡시실릴)벤젠, 1,4-비스(트리에톡시실릴)벤젠, 1,4-비스(트리-n-프로폭시실릴)벤젠, 1,4-비스(트리-iso-프로폭시실릴)벤젠, 1,4-비스(트리-n-부톡시실릴)벤젠, 1,4-비스(트리-sec-부톡시실릴)벤젠, 1,4-비스(트리-tert-부톡시실릴)벤젠 등 들 수 있다.
이들 중, 비스(트리메톡시실릴)메탄, 비스(트리에톡시실릴)메탄, 1,2-비스(트리메톡시실릴)에탄, 1,2-비스(트리에톡시실릴)에탄, 1-(디메톡시메틸실릴)-1-(트리메톡시실릴)메탄, 1-(디에톡시메틸실릴)-1-(트리에톡시실릴)메탄, 1-(디메톡시메틸실릴)-2-(트리메톡시실릴)에탄, 1-(디에톡시메틸실릴)-2-(트리에톡시실릴)에탄, 비스(디메톡시메틸실릴)메탄, 비스(디에톡시메틸실릴)메탄, 1,2-비스(디메톡시메틸실릴)에탄, 1,2-비스(디에톡시메틸실릴)에탄, 1,2-비스(트리메톡시실릴)벤젠, 1,2-비스(트리에톡시실릴)벤젠, 1,3-비스(트리메톡시실릴)벤젠, 1,3-비스(트리에톡시실 릴)벤젠, 1,4-비스(트리메톡시실릴)벤젠, 1,4-비스(트리에톡시실릴)벤젠 등을 바람직한 예로서 들 수 있다.
상기 화합물 1 내지 3은, 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
화합물 1 내지 3으로 표시되는 화합물을 가수분해 및 부분 축합시킬 때, 화학식 1 내지 3에 있어서, R1O-, R2O-, R4O- 및 R5O-로 표시되는 기 1 몰당 0.3 내지 10 몰의 물을 이용하는 것이 바람직하다. 상기 실록산 화합물이 축합물인 경우에는, 폴리스티렌 환산 중량 평균 분자량으로 500 내지 100,000인 것이 바람직하다. 또한, 본 발명에 있어서 완전 가수분해 축합물이란, 실록산 화합물 성분 중 R1O-, R2O-, R4O- 및 R5O-로 표시되는 기가 100 % 가수분해되어 OH기가 됨으로써 완전히 축합된 것을 나타낸다.
1.1.4. 촉매
본 발명의 절연막의 형성 방법에 있어서, (A) 성분에는, 필요에 따라서 촉매가 함유될 수도 있다. 이러한 촉매로는, 유기산, 무기산, 유기 염기, 무기 염기, 금속 킬레이트 등을 들 수 있다.
유기산으로는, 예를 들면 아세트산, 프로피온산, 부탄산, 펜탄산, 헥산산, 헵탄산, 옥탄산, 노난산, 데칸산, 옥살산, 말레산, 메틸말론산, 아디프산, 세박산, 갈산, 부티르산, 멜리트산, 아라퀴돈산, 시킴산, 2-에틸헥산산, 올레산, 스테아르산, 리놀레산, 리놀렌산, 살리실산, 벤조산, p-아미노벤조산, p-톨루엔술폰산, 벤 젠술폰산, 모노클로로아세트산, 디클로로아세트산, 트리클로로아세트산, 트리플루오로아세트산, 포름산, 말론산, 술폰산, 프탈산, 푸마르산, 시트르산, 타르타르산 등을 들 수 있다.
무기산으로는, 예를 들면 염산, 질산, 황산, 불산 및 인산 등을 들 수 있다.
무기 염기로는, 예를 들면 암모니아, 수산화나트륨, 수산화칼륨, 수산화바륨, 수산화칼슘 등을 들 수 있다.
유기 염기로는, 예를 들면 메탄올아민, 에탄올아민, 프로판올아민, 부탄올아민, N-메틸메탄올아민, N-에틸메탄올아민, N-프로필메탄올아민, N-부틸메탄올아민, N-메틸에탄올아민, N-에틸에탄올아민, N-프로필에탄올아민, N-부틸에탄올아민, N-메틸프로판올아민, N-에틸프로판올아민, N-프로필프로판올아민, N-부틸프로판올아민, N-메틸부탄올아민, N-에틸부탄올아민, N-프로필부탄올아민, N-부틸부탄올아민, N,N-디메틸메탄올아민, N,N-디에틸메탄올아민, N,N-디프로필메탄올아민, N,N-디부틸메탄올아민, N,N-디메틸에탄올아민, N,N-디에틸에탄올아민, N,N-디프로필에탄올아민, N,N-디부틸에탄올아민, N,N-디메틸프로판올아민, N,N-디에틸프로판올아민, N,N-디프로필프로판올아민, N,N-디부틸프로판올아민, N,N-디메틸부탄올아민, N,N-디에틸부탄올아민, N,N-디프로필부탄올아민, N,N-디부틸부탄올아민, N-메틸디메탄올아민, N-에틸디메탄올아민, N-프로필디메탄올아민, N-부틸디메탄올아민, N-메틸디에탄올아민, N-에틸디에탄올아민, N-프로필디에탄올아민, N-부틸디에탄올아민, N-메틸디프로판올아민, N-에틸디프로판올아민, N-프로필디프로판올아민, N-부틸디프로판올아민, N-메틸디부탄올아민, N-에틸디부탄올아민, N-프로필디부탄올아민, N-부틸디부탄올아민, N-(아미노메틸)메탄올아민, N-(아미노메틸)에탄올아민, N-(아미노메틸)프로판올아민, N-(아미노메틸)부탄올아민, N-(아미노에틸)메탄올아민, N-(아미노에틸)에탄올아민, N-(아미노에틸)프로판올아민, N-(아미노에틸)부탄올아민, N-(아미노프로필)메탄올아민, N-(아미노프로필)에탄올아민, N-(아미노프로필)프로판올아민, N-(아미노프로필)부탄올아민, N-(아미노부틸)메탄올아민, N-(아미노부틸)에탄올아민, N-(아미노부틸)프로판올아민, N-(아미노부틸)부탄올아민, 메톡시메틸아민, 메톡시에틸아민, 메톡시프로필아민, 메톡시부틸아민, 에톡시메틸아민, 에톡시에틸아민, 에톡시프로필아민, 에톡시부틸아민, 프로폭시메틸아민, 프로폭시에틸아민, 프로폭시프로필아민, 프로폭시부틸아민, 부톡시메틸아민, 부톡시에틸아민, 부톡시프로필아민, 부톡시부틸아민, 메틸아민, 에틸아민, 프로필아민, 부틸아민, N,N-디메틸아민, N,N-디에틸아민, N,N-디프로필아민, N,N-디부틸아민, 트리메틸아민, 트리에틸아민, 트리프로필아민, 트리부틸아민, 테트라메틸암모늄히드록시드, 테트라에틸암모늄히드록시드, 테트라프로필암모늄히드록시드, 테트라부틸암모늄히드록시드, 테트라메틸에틸렌디아민, 테트라에틸에틸렌디아민, 테트라프로필에틸렌디아민, 테트라부틸에틸렌디아민, 메틸아미노메틸아민, 메틸아미노에틸아민, 메틸아미노프로필아민, 메틸아미노부틸아민, 에틸아미노메틸아민, 에틸아미노에틸아민, 에틸아미노프로필아민, 에틸아미노부틸아민, 프로필아미노메틸아민, 프로필아미노에틸아민, 프로필아미노프로필아민, 프로필아미노부틸아민, 부틸아미노메틸아민, 부틸아미노에틸아민, 부틸아미노프로필아민, 부틸아미노부틸아민, 피리딘, 피롤, 피페라진, 피롤리딘, 피페리딘, 피콜린, 모르폴린, 메틸모르폴린, 디아자비시클로 옥란, 디아자비시클로노난, 디아자비시클로운데센 등을 들 수 있다.
금속 킬레이트로는, 예를 들면 트리에톡시ㆍ모노(아세틸아세토네이트)티탄, 트리-n-프로폭시ㆍ모노(아세틸아세토네이트)티탄, 트리-iso-프로폭시ㆍ모노(아세틸아세토네이트)티탄, 트리-n-부톡시ㆍ모노(아세틸아세토네이트)티탄, 트리-sec-부톡시ㆍ모노(아세틸아세토네이트)티탄, 트리-t-부톡시ㆍ모노(아세틸아세토네이트)티탄, 디에톡시ㆍ비스(아세틸아세토네이트)티탄, 디-n-프로폭시ㆍ비스(아세틸아세토네이트)티탄, 디-iso-프로폭시ㆍ비스(아세틸아세토네이트)티탄, 디-n-부톡시ㆍ비스(아세틸아세토네이트)티탄, 디-sec-부톡시ㆍ비스(아세틸아세토네이트)티탄, 디-t-부톡시ㆍ비스(아세틸아세토네이트)티탄, 모노에톡시ㆍ트리스(아세틸아세토네이트)티탄, 모노-n-프로폭시ㆍ트리스(아세틸아세토네이트)티탄, 모노-iso-프로폭시ㆍ트리스(아세틸아세토네이트)티탄, 모노-n-부톡시ㆍ트리스(아세틸아세토네이트)티탄, 모노-sec-부톡시ㆍ트리스(아세틸아세토네이트)티탄, 모노-t-부톡시ㆍ트리스(아세틸아세토네이트)티탄, 테트라키스(아세틸아세토네이트)티탄, 트리에톡시ㆍ모노(에틸아세토아세테이트)티탄, 트리-n-프로폭시ㆍ모노(에틸아세토아세테이트)티탄, 트리-iso-프로폭시ㆍ모노(에틸아세토아세테이트)티탄, 트리-n-부톡시ㆍ모노(에틸아세토아세테이트)티탄, 트리-sec-부톡시ㆍ모노(에틸아세토아세테이트)티탄, 트리-t-부톡시ㆍ모노(에틸아세토아세테이트)티탄, 디에톡시ㆍ비스(에틸아세토아세테이트)티탄, 디-n-프로폭시ㆍ비스(에틸아세토아세테이트)티탄, 디-iso-프로폭시ㆍ비스(에틸아세토아세테이트)티탄, 디-n-부톡시ㆍ비스(에틸아세토아세테이트)티탄, 디-sec-부톡시ㆍ비스(에틸아세토아세테이트)티탄, 디-t-부톡시ㆍ비스(에틸아세토아세테이트)티탄, 모노에톡시ㆍ트리스(에틸아세토아세테이트)티탄, 모노-n-프로폭시ㆍ트리스(에틸아세토아세테이트)티탄, 모노-iso-프로폭시ㆍ트리스(에틸아세토아세테이트)티탄, 모노-n-부톡시ㆍ트리스(에틸아세토아세테이트)티탄, 모노-sec-부톡시ㆍ트리스(에틸아세토아세테이트)티탄, 모노-t-부톡시ㆍ트리스(에틸아세토아세테이트)티탄, 테트라키스(에틸아세토아세테이트)티탄, 모노(아세틸아세토네이트)트리스(에틸아세토아세테이트)티탄, 비스(아세틸아세토네이트)비스(에틸아세토아세테이트)티탄, 트리스(아세틸아세토네이트)모노(에틸아세토아세테이트)티탄 등의 티탄 킬레이트 화합물;
트리에톡시ㆍ모노(아세틸아세토네이트)지르코늄, 트리-n-프로폭시ㆍ모노(아세틸아세토네이트)지르코늄, 트리-iso-프로폭시ㆍ모노(아세틸아세토네이트)지르코늄, 트리-n-부톡시ㆍ모노(아세틸아세토네이트)지르코늄, 트리-sec-부톡시ㆍ모노(아세틸아세토네이트)지르코늄, 트리-t-부톡시ㆍ모노(아세틸아세토네이트)지르코늄, 디에톡시ㆍ비스(아세틸아세토네이트)지르코늄, 디-n-프로폭시ㆍ비스(아세틸아세토네이트)지르코늄, 디-iso-프로폭시ㆍ비스(아세틸아세토네이트)지르코늄, 디-n-부톡시ㆍ비스(아세틸아세토네이트)지르코늄, 디-sec-부톡시ㆍ비스(아세틸아세토네이트)지르코늄, 디-t-부톡시ㆍ비스(아세틸아세토네이트)지르코늄, 모노에톡시ㆍ트리스(아세틸아세토네이트)지르코늄, 모노-n-프로폭시ㆍ트리스(아세틸아세토네이트)지르코늄, 모노-iso-프로폭시ㆍ트리스(아세틸아세토네이트)지르코늄, 모노-n-부톡시ㆍ트리스(아세틸아세토네이트)지르코늄, 모노-sec-부톡시ㆍ트리스(아세틸아세토네이트)지르코늄, 모노-t-부톡시ㆍ트리스(아세틸아세토네이트)지르코늄, 테트라키스(아세틸아세토네이트)지르코늄, 트리에톡시ㆍ모노(에틸아세토아세테이트)지르코늄, 트리-n-프로폭시ㆍ모노(에틸아세토아세테이트)지르코늄, 트리-iso-프로폭시ㆍ모노(에틸아세토아세테이트)지르코늄, 트리-n-부톡시ㆍ모노(에틸아세토아세테이트)지르코늄, 트리-sec-부톡시ㆍ모노(에틸아세토아세테이트)지르코늄, 트리-t-부톡시ㆍ모노(에틸아세토아세테이트)지르코늄, 디에톡시ㆍ비스(에틸아세토아세테이트)지르코늄, 디-n-프로폭시ㆍ비스(에틸아세토아세테이트)지르코늄, 디-iso-프로폭시ㆍ비스(에틸아세토아세테이트)지르코늄, 디-n-부톡시ㆍ비스(에틸아세토아세테이트)지르코늄, 디-sec-부톡시ㆍ비스(에틸아세토아세테이트)지르코늄, 디-t-부톡시ㆍ비스(에틸아세토아세테이트)지르코늄, 모노에톡시ㆍ트리스(에틸아세토아세테이트)지르코늄, 모노-n-프로폭시ㆍ트리스(에틸아세토아세테이트)지르코늄, 모노-iso-프로폭시ㆍ트리스(에틸아세토아세테이트)지르코늄, 모노-n-부톡시ㆍ트리스(에틸아세토아세테이트)지르코늄, 모노-sec-부톡시ㆍ트리스(에틸아세토아세테이트)지르코늄, 모노-t-부톡시ㆍ트리스(에틸아세토아세테이트)지르코늄, 테트라키스(에틸아세토아세테이트)지르코늄, 모노(아세틸아세토네이트)트리스(에틸아세토아세테이트)지르코늄, 비스(아세틸아세토네이트)비스(에틸아세토아세테이트)지르코늄, 트리스(아세틸아세토네이트)모노(에틸아세토아세테이트)지르코늄 등의 지르코늄 킬레이트 화합물; 및
트리스(아세틸아세토네이트)알루미늄, 트리스(에틸아세토아세테이트)알루미늄 등의 알루미늄 킬레이트 화합물 등을 들 수 있다.
이들 촉매의 사용량은 화합물 1 내지 3의 총량 1 몰에 대하여 통상 0.0001 내지 1 몰, 바람직하게는 0.001 내지 0.1 몰이다.
1.2. 막 형성용 조성물의 제조 방법
폴리실록산계 절연막을 형성하기 위한 막 형성용 조성물(이하, 이것을 「조성물 1」이라 함)의 제조 방법에서는, 상술한 화합물 1 내지 화합물 3으로부터 선택되는 1종 이상의 실란 화합물을, 상술한 촉매, 물 및 후술하는 유기 용매의 존재하에서 가수분해 축합을 수행한다.
상기 가수분해 축합은 통상 20 내지 180 ℃에서 10 분 내지 48 시간, 바람직하게는 30 내지 150 ℃에서 10 분 내지 24 시간 정도 행해진다. 반응은 개방 용기 또는 밀폐 용기 중에서 통상적으로 0.05 내지 3 MPa 정도의 압력하에서 행해진다.
이와 같이 하여 얻어지는 조성물 1의 전체 고형분 농도는 바람직하게는 0.5 내지 30 중량%이고, 사용 목적에 따라서 적절하게 조정된다. 본 발명의 막 형성용 조성물의 전체 고형분 농도를 0.5 내지 30 중량%로 함으로써, 절연막의 막 두께가 적당한 범위가 되어, 보존 안정성도 보다 우수해진다. 또한, 이 전체 고형분 농도의 조정은, 필요하다면 농축 및 유기 용매에 의한 희석에 의해서 행할 수 있다.
또한, 조성물 1의 제조 방법에서는, 최종적인 조성물의 pH를 7 이하로 조정하는 것이 바람직하다.
pH를 조정하는 방법으로는, 이하의 (I) 내지 (V)의 방법을 들 수 있다:
(I) pH 조정제를 첨가하는 방법,
(II) 상압 또는 감압하에 조성물 중에서 수산화테트라알킬암모늄을 증류 제거하는 방법,
(III) 질소, 아르곤 등의 가스를 버블링함으로써, 조성물 중에서 수산화테트 라알킬암모늄을 제거하는 방법,
(IV) 이온 교환 수지에 의해 조성물 중에서 수산화테트라알킬암모늄을 제거하는 방법, 및
(V) 추출이나 세정에 의해서 수산화테트라알킬암모늄을 계 밖으로 제거하는 방법.
이들 방법은 각각 조합하여 이용할 수도 있다.
(I)의 방법에서 사용할 수 있는 pH 조정제로는, 무기산이나 유기산을 들 수 있다.
무기산으로는, 예를 들면 염산, 질산, 황산, 불산, 인산, 붕산, 옥살산 등을 들 수 있다.
또한, 유기산으로는, 예를 들면 아세트산, 프로피온산, 부탄산, 펜탄산, 헥산산, 헵탄산, 옥탄산, 노난산, 데칸산, 옥살산, 말레산, 메틸말론산, 아디프산, 세박산, 갈산, 부티르산, 멜리트산, 아라퀴돈산, 시킴산, 2-에틸헥산산, 올레산, 스테아르산, 리놀레산, 리놀렌산, 살리실산, 벤조산, p-아미노벤조산, p-톨루엔술폰산, 벤젠술폰산, 모노클로로아세트산, 디클로로아세트산, 트리클로로아세트산, 트리플루오로아세트산, 포름산, 말론산, 술폰산, 프탈산, 푸마르산, 시트르산, 타르타르산, 숙신산, 푸마르산, 이타콘산, 메사콘산, 시트라콘산, 말산, 글루타르산의 가수분해물, 말레산 무수물의 가수분해물 및 프탈산 무수물의 가수분해물 등을 들 수 있다.
이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
최종적으로, 막 형성용 조성물의 pH는 7 이하, 바람직하게는 1 내지 6으로 조정된다. 이와 같이, 상기 pH 조정제에 의해 상기 범위 내에서 pH를 조정함으로써, 얻어지는 조성물의 저장 안정성이 향상되는 효과가 얻어진다.
pH 조정제의 사용량은, 조성물의 pH가 상기 범위 내에 있는 양이고, 그의 사용량은 적절하게 선택된다.
1.2.1. 유기 용매
또한, 상술한 가수분해 축합은 유기 용매 존재하에서 수행할 수 있다.
이러한 유기 용매로는 알코올계 용매, 케톤계 용매, 아미드계 용매, 에스테르계 용매 및 비양성자계 용매의 군에서 선택된 1종 이상을 들 수 있다.
여기서, 알코올계 용매로는, 메탄올, 에탄올, n-프로판올, iso-프로판올, n-부탄올, iso-부탄올, sec-부탄올, t-부탄올, n-펜탄올, iso-펜탄올, 2-메틸부탄올, sec-펜탄올, t-펜탄올, 3-메톡시부탄올, n-헥산올, 2-메틸펜탄올, sec-헥산올, 2-에틸부탄올, sec-헵탄올, 3-헵탄올, n-옥탄올, 2-에틸헥산올, sec-옥탄올, n-노닐알코올, 2,6-디메틸-4-헵탄올, n-데칸올, sec-운데실알코올, 트리메틸노닐알코올, sec-테트라데실알코올, sec-헵타데실알코올, 페놀, 시클로헥산올, 메틸시클로헥산올, 3,3,5-트리메틸시클로헥산올, 벤질알코올, 디아세톤알코올 등의 모노알코올계 용매;
에틸렌글리콜, 1,2-프로필렌글리콜, 1,3-부틸렌글리콜, 2,4-펜탄디올, 2-메틸-2,4-펜탄디올, 2,5-헥산디올, 2,4-헵탄디올, 2-에틸-1,3-헥산디올, 디에틸렌글리콜, 디프로필렌글리콜, 트리에틸렌글리콜, 트리프로필렌글리콜 등의 다가 알코올계 용매; 및
에틸렌글리콜 모노메틸에테르, 에틸렌글리콜 모노에틸에테르, 에틸렌글리콜 모노프로필에테르, 에틸렌글리콜 모노부틸에테르, 에틸렌글리콜 모노헥실에테르, 에틸렌글리콜 모노페닐에테르, 에틸렌글리콜 모노-2-에틸부틸에테르, 디에틸렌글리콜 모노메틸에테르, 디에틸렌글리콜 모노에틸에테르, 디에틸렌글리콜 모노프로필에테르, 디에틸렌글리콜 모노부틸에테르, 디에틸렌글리콜 모노헥실에테르, 프로필렌글리콜 모노메틸에테르, 프로필렌글리콜 모노에틸에테르, 프로필렌글리콜 모노프로필에테르, 프로필렌글리콜 모노부틸에테르, 디프로필렌글리콜 모노메틸에테르, 디프로필렌글리콜 모노에틸에테르, 디프로필렌글리콜 모노프로필에테르 등의 다가 알코올 부분 에테르계 용매 등을 들 수 있다.
이들 알코올계 용매는 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
케톤계 용매로는, 아세톤, 메틸에틸케톤, 메틸-n-프로필케톤, 메틸-n-부틸케톤, 디에틸케톤, 메틸-iso-부틸케톤, 메틸-n-펜틸케톤, 에틸-n-부틸케톤, 메틸-n-헥실케톤, 디-iso-부틸케톤, 트리메틸노나논, 시클로헥사논, 2-헥사논, 메틸시클로헥사논, 2,4-펜탄디온, 아세토닐아세톤, 아세토페논, 펜촌(fenchone) 등 이외에도, 아세틸아세톤, 2,4-헥산디온, 2,4-헵탄디온, 3,5-헵탄디온, 2,4-옥탄디온, 3,5-옥탄디온, 2,4-노난디온, 3,5-노난디온, 5-메틸-2,4-헥산디온, 2,2,6,6-테트라메틸-3,5-헵탄디온, 1 ,1,1,5,5,5-헥사플루오로-2,4-헵탄디온 등의 β-디케톤류 등을 들 수 있다.
이들 케톤계 용매는 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
아미드계 용매로는, 포름아미드, N-메틸포름아미드, N,N-디메틸포름아미드, N-에틸포름아미드, N,N-디에틸포름아미드, 아세트아미드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-에틸아세트아미드, N,N-디에틸아세트아미드, N-메틸프로피온아미드, N-메틸피롤리돈, N-포르밀모르폴린, N-포르밀피페리딘, N-포르밀피롤리딘, N-아세틸모르폴린, N-아세틸피페리딘, N-아세틸피롤리딘 등을 들 수 있다.
이들 아미드계 용매는 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
에스테르계 용매로는, 디에틸카르보네이트, 탄산에틸렌, 탄산프로필렌, 탄산 디에틸, 아세트산메틸, 아세트산에틸, γ-부티로락톤, γ-발레로락톤, 아세트산 n-프로필, 아세트산 iso-프로필, 아세트산 n-부틸, 아세트산 iso-부틸, 아세트산 sec-부틸, 아세트산 n-펜틸, 아세트산 sec-펜틸, 아세트산 3-메톡시부틸, 아세트산 메틸펜틸, 아세트산 2-에틸부틸, 아세트산 2-에틸헥실, 아세트산 벤질, 아세트산 시클로헥실, 아세트산 메틸시클로헥실, 아세트산 n-노닐, 아세토아세트산메틸, 아세토아세트산에틸, 아세트산 에틸렌글리콜 모노메틸에테르, 아세트산 에틸렌글리콜 모노에틸에테르, 아세트산 디에틸렌글리콜 모노메틸에테르, 아세트산 디에틸렌글리콜 모노에틸에테르, 아세트산 디에틸렌글리콜 모노-n-부틸에테르, 아세트산 프로필렌글리콜 모노메틸에테르, 아세트산 프로필렌글리콜 모노에틸에테르, 아세트산 프로필렌글리콜 모노프로필에테르, 아세트산 프로필렌글리콜 모노부틸에테르, 아세트산 디프로필렌글리콜 모노메틸에테르, 아세트산 디프로필렌글리콜 모노에틸에테르, 디아세트산 글리콜, 아세트산메톡시트리글리콜, 프로피온산에틸, 프로피온산 n-부틸, 프로피온산 iso-아밀, 옥살산 디에틸, 옥살산 디-n-부틸, 락트산메틸, 락트산에틸, 락트산 n-부틸, 락트산 n-아밀, 말론산 디에틸, 프탈산 디메틸, 프탈산 디에틸 등을 들 수 있다.
이들 에스테르계 용매는 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 비양성자계 용매로는, 아세토니트릴, 디메틸술폭시드, N,N,N',N'-테트라에틸술파미드, 헥사메틸인산트리아미드, N-메틸모르포론, N-메틸피롤, N-에틸피롤, N-메틸-Δ3-피롤린, N-메틸피페리딘, N-에틸피페리딘, N,N-디메틸피페라진, N-메틸이미다졸, N-메틸-4-피페리돈, N-메틸-2-피페리돈, N-메틸-2-피롤리돈, 1,3-디메틸-2-이미다졸리디논, 1,3-디메틸테트라히드로-2(1H)-피리미디논 등을 들 수 있다.
이들 비양성자계 용매는 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
이들 유기 용매 중에서 특히 알코올류가 바람직하다. 이들 유기 용매는 1종 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다.
1.3. 폴리실록산계 절연막의 막 형성 방법
폴리실록산계 절연막은, 상기 조성물 1을 기재에 도포하고, 용매를 제거한 후, 도막을 가열에 의해 경화시킴으로써 형성할 수 있다. 우선, 조성물 1의 기재에의 도포 방법으로는, 스핀 코팅, 디핑, 롤러 블레이드, 스프레이법 등을 들 수 있다. 이때의 막 두께는, 건조 막 두께로서, 1회 도포로 두께 0.01 내지 1.5 ㎛ 정도, 2회 도포로는 두께 0.02 내지 3 ㎛ 정도의 도막을 형성할 수 있다.
가열하는 방법으로는, 예를 들면 60 내지 600 ℃ 정도의 온도에서 통상적으로 1 분 내지 240 분 정도 가열하여 도막을 건조시킬 수 있다. 이 경우, 가열 방법으로는, 핫 플레이트, 오븐, 퍼니스(furnace) 등을 사용할 수 있고, 가열 분위기로는, 대기하, 질소 분위기하, 아르곤 분위기하, 진공하, 산소 농도가 제어된 감압하 등에서 행할 수 있다. 또한, 전자선이나 자외선을 조사함으로써도 도막을 형성시킬 수 있고, 이 경우에는, 건조 시간이 단축 가능하다는 점에서 바람직하다.
2. 폴리카르보실란계 절연막의 형성 방법
2.1. 폴리카르보실란계 절연막을 형성하기 위한 성분((B) 성분)
(B) 성분은 하기 화학식 4로 표시되는 폴리카르보실란 화합물(이하, 「화합물 4」라고 하는 경우도 있음)이다. 또한, 이하의 설명에 있어서, (B) 성분이라 할 때, 상기 폴리카르보실란 화합물이 유기 용매에 용해 또는 분산되어 있는 경우도 포함되는 것으로 한다.
<화학식 4>
상기 화학식 4 중, R8 내지 R11은 수소 원자, 할로겐 원자, 히드록실기, 알콕실기, 술폰기, 메탄술폰기, 트리플루오로메탄술폰기 또는 유기기를 나타낸다. 유기기로는, 화합물 1에서 예시한 기와 동일한 것을 들 수 있다. 또한, R8 내지 R11은 동일하거나 상이한 기일 수 있다.
R12 내지 R14는 치환 또는 비치환의 알킬렌기, 알케닐기, 알키닐기 또는 아릴렌기를 나타낸다. 또한, R12 내지 R14는 동일하거나 상이한 기일 수 있다.
알킬렌기로는 메틸렌기, 에틸렌기, 트리메틸렌기, 테트라메틸렌기 등을 들 수 있다.
알케닐기로는 비닐렌기, 프로페닐렌기 등을 들 수 있다.
알키닐기로는 에티닐렌기 등을 들 수 있다.
아릴렌기로는 페닐렌기, 나프틸렌기 등을 들 수 있다.
x, y 및 z는 0 내지 10,000의 정수이고, 바람직하게는 10<x+y+z<20,000, 보다 바람직하게는 500<x+y+z<10,000의 조건을 만족시키는 값인 것이 바람직하다. 저분자량 폴리카르보실란의 경우, 휘발 성분이 많아서, 막 형성 과정에서 각종 문제를 일으키는 경우가 있다.
폴리카르보실란계 화합물로는, 폴리아릴히드리드카르보실란, 폴리디메틸카르보실란, 폴리디메톡시카르보실란, 폴리메틸히드리드카르보실란, 폴리디히드로카르보실란 등을 들 수 있다.
2.2. 막 형성용 조성물의 제조 방법
폴리카르보실란계 절연막을 형성하기 위한 막 형성용 조성물(이하, 이것을 「조성물 2」라고도 함)의 제조 방법에서는, 상술한 화합물 4를 용매에 용해시켜 얻어진다.
이와 같이 하여 얻어지는 조성물 2의 전체 고형분 농도는 바람직하게는 0.1 내지 25 중량%이고, 사용 목적에 따라서 적절하게 조정된다. 조성물 2의 전체 고형분 농도를 상기 범위로 함으로써 절연막의 막 두께가 적당한 범위가 되고, 보존 안정성도 보다 우수해진다. 또한, 이 전체 고형분 농도의 조정은, 필요하다면 농축 및 유기 용매에 의한 희석에 의해서 행할 수 있다. 조성물 2의 비율은, 폴리카르보실란 화합물이 0.1 내지 20 중량%, 용매가 99.9 내지 80 중량%인 것이 바람직하다. 폴리카르보실란계 화합물의 비율이 이 범위에 있는 경우, 얻어진 조성물을 스핀 코팅법에 의해 도포하는 데 적합한 조성물로 사용할 수 있다.
조성물 2는, 필요에 따라서 계면활성제, pH 조정제, 레벨링제 등의 첨가제를 포함할 수 있다.
2.2.1. 유기 용매
조성물 2를 제조하기 위한 유기 용매로는, 케톤계 용매, 에스테르계 용매, 알코올계 용매, 방향족계 용매 등을 들 수 있다.
케톤계 용매로는, 아세톤, 메틸에틸케톤, 메틸-n-프로필케톤, 메틸-n-부틸케톤, 디에틸케톤, 메틸-iso-부틸케톤, 메틸-n-펜틸케톤, 에틸-n-부틸케톤, 메틸-n-헥실케톤, 디-iso-부틸케톤, 트리메틸노나논, 시클로헥사논, 2-헥사논, 메틸시클로헥사논, 2,4-펜탄디온, 아세토닐아세톤, 아세토페논 및 펜촌 등 이외에도, 아세틸아세톤, 2,4-헥산디온, 2-헵타논, 2,4-헵탄디온, 3,5-헵탄디온, 2,4-옥탄디온, 3,5-옥탄디온, 2,4-노난디온, 3,5-노난디온, 5-메틸-2,4-헥산디온, 2,2,6,6-테트라메틸-3,5-헵탄디온, 1,1,1,5,5,5-헥사플루오로-2,4-헵탄디온 등의 β-디케톤류 등을 들 수 있다.
에스테르계 용매로는, 디에틸카르보네이트, 탄산에틸렌, 탄산프로필렌, 탄산 디에틸, 아세트산메틸, 아세트산에틸, γ-부티로락톤, γ-발레로락톤, 아세트산 n-프로필, 아세트산 iso-프로필, 아세트산 n-부틸, 아세트산 iso-부틸, 아세트산 sec-부틸, 아세트산 n-펜틸, 아세트산 sec-펜틸, 아세트산 3-메톡시부틸, 아세트산 메틸펜틸, 아세트산 2-에틸부틸, 아세트산 2-에틸헥실, 아세트산 벤질, 아세트산 시클로헥실, 아세트산 메틸시클로헥실, 아세트산 n-노닐, 아세토아세트산메틸, 아세토아세트산에틸, 아세트산 에틸렌글리콜 모노메틸에테르, 아세트산 에틸렌글리콜 모노에틸에테르, 아세트산 디에틸렌글리콜 모노메틸에테르, 아세트산 디에틸렌글리콜 모노에틸에테르, 아세트산 디에틸렌글리콜 모노-n-부틸에테르, 아세트산 프로필렌글리콜 모노메틸에테르, 아세트산 프로필렌글리콜 모노에틸에테르, 아세트산 프로필렌글리콜 모노프로필에테르, 아세트산 프로필렌글리콜 모노부틸에테르, 아세트산 디프로필렌글리콜 모노메틸에테르, 아세트산 디프로필렌글리콜 모노에틸에테르, 디아세트산 글리콜, 아세트산메톡시트리글리콜, 프로피온산에틸, 프로피온산 n-부틸, 프로피온산 iso-아밀, 옥살산 디에틸, 옥살산 디-n-부틸, 락트산메틸, 락트산에틸, 락트산 n-부틸, 락트산 n-아밀, 말론산 디에틸, 프탈산 디메틸, 프탈산 디에틸 등을 들 수 있다.
알코올계 용매로는, 에틸렌글리콜 모노메틸에테르, 에틸렌글리콜 모노에틸에테르, 에틸렌글리콜 모노프로필에테르, 에틸렌글리콜 모노부틸에테르, 에틸렌글리콜 모노헥실에테르, 에틸렌글리콜 모노페닐에테르, 에틸렌글리콜 모노-2-에틸부틸 에테르, 디에틸렌글리콜 모노메틸에테르, 디에틸렌글리콜 모노에틸에테르, 디에틸렌글리콜 모노프로필에테르, 디에틸렌글리콜 모노부틸에테르, 디에틸렌글리콜 모노헥실에테르, 프로필렌글리콜 모노메틸에테르, 프로필렌글리콜 모노에틸에테르, 프로필렌글리콜 모노프로필에테르, 프로필렌글리콜 모노부틸에테르, 디프로필렌글리콜 모노메틸에테르, 디프로필렌글리콜 모노에틸에테르, 디프로필렌글리콜 모노프로필에테르 등의 다가 알코올 부분 에테르계 용매 등을 들 수 있다.
방향족계 용매로는, 벤젠, 톨루엔, 크실렌, 메시틸렌 등을 들 수 있다.
2.2.2. 계면활성제
계면활성제로는, 예를 들면 비이온계 계면활성제, 음이온계 계면활성제, 양이온계 계면활성제, 양쪽성 계면활성제 등을 들 수 있고, 또한 불소계 계면활성제, 실리콘계 계면활성제, 폴리알킬렌옥시드계 계면활성제, 폴리(메트)아크릴레이트계 계면활성제 등을 들 수 있으며, 바람직하게는 불소계 계면활성제 및 실리콘계 계면활성제를 들 수 있다.
불소계 계면활성제로는, 예를 들면 1,1,2,2-테트라플루오로옥틸(1,1,2,2-테트라플루오로프로필)에테르, 1,1,2,2-테트라플루오로옥틸헥실에테르, 옥타에틸렌글리콜 디(1,1,2,2-테트라플루오로부틸)에테르, 헥사에틸렌글리콜(1,1,2,2,3,3-헥사플루오로펜틸)에테르, 옥타프로필렌글리콜 디(1,1,2,2-테트라플루오로부틸)에테르, 헥사프로필렌글리콜 디(1,1,2,2,3,3-헥사플루오로펜틸)에테르, 퍼플루오로도데실술폰산나트륨, 1,1,2,2,8,8,9,9,10,10-데카플루오로도데칸, 1,1,2,2,3,3-헥사플루오로데칸, N-[3-(퍼플루오로옥탄술폰아미드)프로필]-N,N'-디메틸-N-카르복시메틸렌암 모늄베타인, 퍼플루오로알킬술폰아미드 프로필트리메틸암모늄염, 퍼플루오로알킬-N-에틸술포닐글리신염, 인산비스(N-퍼플루오로옥틸술포닐-N-에틸아미노에틸), 모노퍼플루오로알킬에틸인산에스테르 등의 말단, 주쇄 및 측쇄 중 적어도 한 부위에는 플루오로알킬 또는 플루오로알킬렌기를 갖는 화합물을 포함하는 불소계 계면활성제를 들 수 있다.
또한, 시판품으로는, 메가팩 F1, 42D, 동 F172, 동 F173, 동 F183[이상, 다이 닛본 잉크 가가꾸 고교(주) 제조], 에프톱 EF301, 동 303, 동 352[신아끼다 가세이(주) 제조], 플로라드 FC-430, 동 FC-431[스미또모 쓰리엠(주) 제조], 아사히가드 AG710, 사프론 S-382, 동 SC-101, 동 SC-102, 동 SC-103, 동 SC-104, 동 SC-105, 동 SC-106[아사히 글래스(주) 제조], BM-1000, BM-1100[유쇼(주) 제조], NBX-15[(주)네오스] 등의 명칭으로 시판되는 불소계 계면활성제를 들 수 있다. 이들 중에서도, 상기 메가팩 F172, BM-1000, BM-1100 및 NBX-15가 특히 바람직하다.
실리콘계 계면활성제로는, 예를 들면 SH7PA, SH21PA, SH30PA, ST94PA[모두 도레이ㆍ다우코닝ㆍ실리콘(주) 제조] 등을 사용할 수 있다. 이들 중에서도, 상기 SH28PA 및 SH30PA가 특히 바람직하다.
계면활성제의 사용량은 (B) 성분 100 중량부에 대하여 통상적으로 0.00001 내지 1 중량부이다.
이들은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
상술한 첨가물 외에 레벨링제 등이 포함되어 있을 수도 있다.
2.3. 폴리카르보실란계 절연막의 형성 방법
폴리카르보실란계 절연막은, 상기 조성물 2를 1.3.에서 서술한 폴리실록산계 절연막 상에 도포하고, 용매를 제거한 후, 도막을 가열하여 경화시킴으로써 형성할 수 있다. 조성물 2의 도포 방법으로는, 스핀 코팅, 디핑, 롤러 블레이드, 스프레이법, 스캔 코팅, 슬릿 다이(slit die)코팅 등을 들 수 있다.
폴리카르보실란계 절연막의 막 두께는, 폴리카르보실란계 절연막 상에 형성되는 유기계 절연막을 예를 들면, RIE에 의해 에칭할 때, 상기 폴리카르보실란계 절연막보다 아래에 위치하는 폴리실록산계 절연막이, 에칭 손상을 받지 않을 정도이면 된다. 이 점을 고려하면, 폴리카르보실란계 절연막의 막 두께는, 예를 들면 건조 막 두께로서, 바람직하게는 0.5 내지 100 nm, 보다 바람직하게는 1 내지 10 nm이다. 원하는 막 두께의 폴리카르보실란계 절연막을 형성하기 위해서는, 예를 들면 조성물 2의 점도를 조정하거나, 도포 횟수를 적절하게 선택할 수 있다.
경화(cure)를 위한 도막의 가열은, 폴리카르보실란계 화합물이 중합에 의해서 삼차원 가교되는 데 적합한 온도에서 행해지는 것이 바람직하고, 바람직하게는 60 ℃ 이상, 보다 바람직하게는 80 내지 600 ℃ 정도의 온도에서 행해진다. 가열 시간은 특별히 한정되지 않지만, 통상적으로 1 분 내지 240 분 정도이다. 도막의 가열 방법으로는, 핫 플레이트, 오븐, 퍼니스 등을 사용할 수 있고, 가열 분위기로는, 대기하, 질소 분위기하, 아르곤 분위기하, 진공하, 산소 농도가 제어된 감압하 등에서 행할 수 있다.
3. 유기계 절연막의 형성 방법
3.1. 유기계 절연막을 형성하기 위한 성분
본 발명의 유기계 절연막은, 폴리아릴렌, 폴리아릴렌에테르, 폴리옥사졸린 및 폴리벤조시클로부텐 골격을 갖는 중합체로부터 선택되는 1종 이상을 주성분으로 하는 막이다.
이러한 중합체로는, 하기 화학식 5 내지 7, 11 및 16으로부터 선택되는 1종 이상의 반복 구조 단위를 포함하는 중합체를 포함하는 것들이 예시된다.
(화학식 5 내지 7 중, R8 내지 R12는 각각 독립적으로 탄소수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소수 1 내지 20의 알콕실기, 아릴기, 또는 할로겐 원자를 나타내고, X는 -CQQ'-(여기서, Q와 Q'는 동일하거나 상이할 수도 있고, 할로겐화 알킬기, 알킬기, 수소 원자, 할로겐 원자 또는 아릴기를 나타냄)로 표시되는 기 및 플루오레닐렌기로 이루어지는 군에서 선택되는 1종 이상을 나타내고, Y 는 -O-, -CO-, -COO-, -CONH-, -S-, -SO2- 및 페닐렌기의 군에서 선택되는 1종 이상을 나타내고, e는 0 또는 1을 나타내고, o 내지 s는 0 내지 4의 정수를 나타내고, f는 5 내지 100 몰%, g는 0 내지 95 몰%, h는 0 내지 95 몰%(단, f+g+h=100 몰%), i는 0 내지 100 몰%, j는 0 내지 100 몰%(단, i+j=100 몰%)이고, A 및 B는 각각 독립적으로 하기 화학식 8 내지 10으로 표시되는 2가의 방향족기로 이루어지는 군에서 선택되는 1종 이상의 기를 나타냄);
(화학식 8 내지 10 중, R14, R15, R20 및 R21은 독립적으로 단결합, -O-, -CO-, -CH2-, -COO-, -CONH-, -S-, -SO2-, 페닐렌기, 이소프로필리덴기, 헥사플루오로이소 프로필리덴기, 디페닐메틸리덴기, 플루오레닐렌기, 또는 화학식
로 표시되는 기를 나타내고, R16 내지 R18, R19 및 R22 내지 R24는 독립적으로 탄소 원자수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소 원자수 1 내지 20의 알콕실기 또는 아릴기를 나타내고, k는 0 내지 3의 정수를 나타내고, l은 2 또는 3의 정수를 나타내고, t 내지 z는 독립적으로 0 내지 4의 정수를 나타냄);
(화학식 11 중, R13 및 R13'는 수소 원자 또는 하기 화학식 12 및 13으로 표시되는 방향족기의 군에서 선택되는 1종 이상의 기를 나타내고, W1 및 W2는 하기 화학식 14 및 15로 표시되는 2가의 방향족기로 이루어지는 군에서 선택되는 1종 이상의 기를 나타냄);
(화학식 12 및 13 중, R25는 할로겐 원자, 탄소 원자수 1 내지 20의 탄화수소기, 할로겐화 알킬기, 탄소 원자수 1 내지 20의 알콕실기, 페녹시기 또는 아릴기를 나타내고, m'는 0 내지 5의 정수를 나타내고, n'는 0 내지 7의 정수를 나타냄);
(화학식 14 및 15 중, R25는 할로겐 원자, 탄소 원자수 1 내지 20의 탄화수소기, 할로겐화 알킬기, 탄소 원자수 1 내지 20의 알콕실기, 페녹시기 또는 아릴기를 나타내고, R26은 단결합, -O-, -CO-, -CH2-, -COO-, -CONH-, -S-, -SO2-, 페닐렌기, 이소프로필리덴기, 헥사플루오로이소프로필리덴기, 디페닐메틸리덴기, 메틸페닐메틸리덴기, 트리플루오로메틸메틸메틸리덴기, 트리플루오로메틸페닐메틸리덴기, 플루오레닐렌기, 또는 화학식
로 표시되는 기를 나타내는데, 상기 식 중, R27은 독립적으로 수소 원자, 탄소 원자수 1 내지 4의 탄화수소기 또는 페닐기를 나타내고, a1 및 a2는 독립적으로 0 내지 4의 정수를 나타내고, a3은 0 내지 6의 정수를 나타냄);
(화학식 16 중, n은 2 내지 1000의 정수이며, X는 화학식 17로부터, Y는 화학식 18 또는 화학식 19로부터 각각 선택됨);
(화학식 17 중, X1은 화학식
로부터 선택되는 구조를 나타내고, 이들 구조 중의 벤젠환 상의 수소 원자 중 1개 이상은, 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, t-부틸기 및 페닐기로 이루어지는 군에서 선택되는 유기기로 치환될 수도 있음).
3.2. 유기계 절연막 형성용 조성물의 제조 방법
유기계 절연막을 위한 막 형성용 조성물(이하, 「조성물 3」이라 함)은, 상기 화학식 5 내지 7, 11 및 16으로 표시되는 중합체로부터 선택되는 1종 이상을 용매에 용해 또는 분산시킴으로써 얻어지는 것이다. 우선, 화학식 5 내지 7, 11 및 16으로 표시되는 중합체의 제조 방법에 대하여 설명한다.
3.2.1. 화합물 5
화학식 5로 표시되는 중합체(화합물 5)는, 예를 들면 하기 화학식 20으로 표시되는 화합물 20을 단량체로 하여, 전이 금속 화합물을 포함하는 촉매계의 존재하에 중합시킴으로써 제조할 수 있다.
(화학식 20 중, R8 및 R9는 각각 독립적으로 탄소수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소수 1 내지 20의 알콕실기, 아릴기 또는 할로겐 원자를 나타내고, X는 -CQQ'-(여기서, Q와 Q'는 동일하거나 상이할 수도 있으며, 할로겐화 알킬기, 알킬기, 수소 원자, 할로겐 원자 또는 아릴기를 나타냄)로 표시되는 기 및 플루오레닐렌기로 이루어지는 군에서 선택되는 1종 이상을 나타내고, o 및 p는 0 내지 4의 정수를 나타내고, Z는 알킬기, 할로겐화 알킬기 또는 아릴기를 나타낸다.)
상기 화학식 20 중의 X를 구성하는 Q 및 Q' 중, 알킬기로는 메틸기, 에틸기, iso-프로필기, n-프로필기, 부틸기, 펜틸기, 헥실기 등을 들 수 있고; 할로겐화 알킬기로는 트리플루오로메틸기, 펜타플루오로에틸기 등을 들 수 있고; 아릴알킬기로는 벤질기, 디페닐메틸기 등; 아릴기로는, 페닐기, 비페닐기, 톨릴기, 펜타플루오로페닐기 등을 들 수 있다.
또한, 상기 화학식 20 중의 -OSO2Z를 구성하는 Z로는, 알킬기로서 메틸기, 에틸기 등을; 할로겐화 알킬기로서 트리플루오로메틸기, 펜타플루오로에틸기 등을; 아릴기로서 페닐기, 비페닐기, p-톨릴기, p-펜타플루오로페닐기 등을 들 수 있다. 상기 화학식 20 중의 X로는 하기 화학식 21 내지 26으로 표시되는 2가의 기가 바람직하다. 이들 중에서는, 화학식 26으로 표시되는 플루오레닐렌기가 보다 바람직하다.
상기 화학식 20으로 표시되는 화합물 20(단량체)의 구체예로는, 예를 들면 2,2-비스(4-메틸술포닐옥시페닐)헥사플루오로프로판, 비스(4-메틸술포닐옥시페닐)메탄, 비스(4-메틸술포닐옥시페닐)디페닐메탄, 2,2-비스(4-메틸술포닐옥시-3-메틸페닐)헥사플루오로프로판, 2,2-비스(4-메틸술포닐옥시-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(4-메틸술포닐옥시-3,5-디메틸페닐)헥사플루오로프로판, 2,2-비스(4-메틸술포닐옥시페닐)프로판, 2,2-비스(4-메틸술포닐옥시-3-메틸페닐)프로판, 2,2-비스(4-메틸술포닐옥시-3-프로페닐페닐)프로판, 2,2-비스(4-메틸술포닐옥시-3,5-디메틸페닐)프로판, 2,2-비스(4-메틸술포닐옥시-3-플루오로페닐)프로판, 2,2-비스(4-메틸술포닐옥시-3,5-디플루오로페닐)프로판, 2,2-비스(4-트리플루오로메틸술포닐옥시페닐)프로판, 2,2-비스(4-트리플루오로메틸술포닐옥시-3-프로페닐페닐)프로판, 2,2-비스(4-페닐술포닐옥시페닐)프로판, 2,2-비스(4-페닐술포닐옥시-3-메틸페닐)프로판, 2,2-비스(4-페닐술포닐옥시-3-프로페닐페닐)프로판, 2,2-비스(4-페닐술포닐옥시-3,5-디메틸페닐)프로판, 2,2-비스(4-페닐술포닐옥시-3-플루오로페닐) 디페닐메탄, 2,2-비스(p-톨릴술포닐옥시페닐)프로판, 2,2-비스(p-톨릴술포닐옥시-3-메틸페닐)프로판, 2,2-비스(p-톨릴술포닐옥시-3,5-디메틸페닐)프로판, 2,2-비스(p-톨릴술포닐옥시-3-프로페닐페닐)프로판, 비스(p-톨릴술포닐옥시-3,5-디메틸페닐)프로판, 2,2-비스(p-톨릴술포닐옥시-3-메틸페닐)프로판, 2,2-비스(p-톨릴술포닐옥시-3,5-디메틸페닐)프로판, 2,2-비스(p-톨릴술포닐옥시-3-프로페닐페닐)프로판, 비스(p-톨릴술포닐옥시-3-플루오로페닐)프로판, 비스(p-톨릴술포닐옥시-3,5-디플루오로페닐)프로판, 9,9-비스(4-메틸술포닐옥시페닐)플루오렌, 9,9-비스(4-메틸술포닐옥시-3-메틸페닐)플루오렌, 9,9-비스(4-메틸술포닐옥시-3,5-디메틸페닐)플루오렌, 9,9-비스(4-메틸술포닐옥시-3-프로페닐페닐)플루오렌, 9,9-비스(4-메틸술포닐옥시-3-페닐페닐)플루오렌, 비스(4-메틸술포닐옥시-3-메틸페닐)디페닐메탄, 비스(4-메틸술포닐옥시-3,5-디메틸페닐)디페닐메탄, 비스(4-메틸술포닐옥시-3-프로페닐페닐)디페닐메탄, 비스(4-메틸술포닐옥시-3-플루오로페닐)디페닐메탄, 비스(4-메틸술포닐옥시-3,5-디플루오로페닐)디페닐메탄, 9,9-비스(4-메틸술포닐옥시-3-플루오로페닐)플루오렌, 9,9-비스(4-메틸술포닐옥시-3,5-디플루오로페닐)플루오렌, 비스(4-메틸술포닐옥시페닐)메탄, 비스(4-메틸술포닐옥시-3-메틸페닐)메탄, 비스(4-메틸술포닐옥시-3,5-디메틸페닐)메탄, 비스(4-메틸술포닐옥시-3-프로페닐페닐)메탄, 비스(4-메틸술포닐옥시페닐)트리플루오로메틸페닐메탄, 비스(4-메틸술포닐옥시페닐)페닐메탄, 2,2-비스(4-트리플루오로메틸술포닐옥시페닐)헥사플루오로프로판, 비스(4-트리플루오로메틸술포닐옥시페닐)메탄, 비스(4-트리플루오로메틸술포닐옥시페닐)디페닐메탄, 2,2-비스(4-트리플루오로메틸술포닐옥시-3-메틸페닐)헥사플루오로 프로판, 2,2-비스(4-트리플루오로메틸술포닐옥시-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(4-트리플루오로메틸술포닐옥시-3,5-디메틸페닐)헥사플루오로프로판, 9,9-비스(4-트리플루오로메틸술포닐옥시페닐)플루오렌, 9,9-비스(4-트리플루오로메틸술포닐옥시-3-메틸페닐)플루오렌, 9,9-비스(4-트리플루오로메틸술포닐옥시-3,5-디메틸페닐)플루오렌, 9,9-비스(4-트리플루오로메틸술포닐옥시-3-프로페닐페닐)플루오렌, 9,9-비스(4-트리플루오로메틸술포닐옥시-3-페닐페닐)플루오렌, 비스(4-트리플루오로메틸술포닐옥시-3-메틸페닐)디페닐메탄, 비스(4-트리플루오로메틸술포닐옥시-3,5-디메틸페닐)디페닐메탄, 비스(4-트리플루오로메틸술포닐옥시-3-프로페닐페닐)디페닐메탄, 비스(4-트리플루오로메틸술포닐옥시-3-플루오로페닐)디페닐메탄, 비스(4-트리플루오로메틸술포닐옥시-3,5-디플루오로페닐)디페닐메탄, 9,9-비스(4-트리플루오로메틸술포닐옥시-3-플루오로페닐)플루오렌, 9,9-비스(4-트리플루오로메틸술포닐옥시-3,5-디플루오로페닐)플루오렌, 비스(4-트리플루오로메틸술포닐옥시페닐)메탄, 비스(4-트리플루오로메틸술포닐옥시-3-메틸페닐)메탄, 비스(4-트리플루오로메틸술포닐옥시-3,5-디메틸페닐)메탄, 비스(4-트리플루오로메틸술포닐옥시-3-프로페닐페닐)메탄, 비스(4-트리플루오로메틸술포닐옥시페닐)트리플루오로메틸페닐메탄, 비스(4-트리플루오로메틸술포닐옥시페닐), 2,2-비스(4-페닐술포닐옥시페닐)헥사플루오로프로판, 비스(4-페닐술포닐옥시페닐)메탄, 비스(4-페닐술포닐옥시페닐)디페닐메탄, 2,2-비스(4-페닐술포닐옥시-3-메틸페닐)헥사플루오로프로판, 2,2-비스(4-페닐술포닐옥시-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(4-페닐술포닐옥시-3,5-디메틸페닐)헥사플루오로프로판, 9,9-비스(4-페닐술포닐옥시페닐)플루오렌, 9,9-비스(4-페닐술포닐옥시-3-메틸페닐)플루오렌, 9,9-비스(4-페닐술포닐옥시-3,5-디메틸페닐)플루오렌, 9,9-비스(4-페닐술포닐옥시-3-프로페닐페닐)플루오렌, 9,9-비스(4-페닐술포닐옥시-3-페닐페닐)플루오렌, 비스(4-페닐술포닐옥시-3-메틸페닐)디페닐메탄, 비스(4-페닐술포닐옥시-3,5-디메틸페닐)디페닐메탄, 비스(4-페닐술포닐옥시-3-프로페닐페닐)디페닐메탄, 비스(4-페닐술포닐옥시-3-플루오로페닐)디페닐메탄, 비스(4-페닐술포닐옥시-3,5-디플루오로페닐)디페닐메탄, 9,9-비스(4-페닐술포닐옥시-3-플루오로페닐)플루오렌, 9,9-비스(4-페닐술포닐옥시-3,5-디플루오로페닐)플루오렌, 비스(4-페닐술포닐옥시페닐)메탄, 비스(4-페닐술포닐옥시-3-메틸페닐)메탄, 비스(4-페닐술포닐옥시-3,5-디메틸페닐)메탄, 비스(4-페닐술포닐옥시-3-프로페닐페닐)메탄, 비스(4-페닐술포닐옥시페닐)트리플루오로메틸페닐메탄, 비스(4-페닐술포닐옥시페닐)페닐메탄, 2,2-비스(p-톨릴술포닐옥시페닐)헥사플루오로프로판, 비스(p-톨릴술포닐옥시페닐)메탄, 비스(p-톨릴술포닐옥시페닐)디페닐메탄, 2,2-비스(p-톨릴술포닐옥시-3-메틸페닐)헥사플루오로프로판, 2,2-비스(p-톨릴술포닐옥시-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(p-톨릴술포닐옥시-3,5-디메틸페닐)헥사플루오로프로판, 9,9-비스(p-톨릴술포닐옥시페닐)플루오렌, 9,9-비스(p-톨릴술포닐옥시-3-메틸페닐)플루오렌, 9,9-비스(p-톨릴술포닐옥시-3,5-디메틸페닐)플루오렌, 9,9-비스(p-톨릴술포닐옥시-3-프로페닐페닐)플루오렌, 9,9-비스(p-톨릴술포닐옥시-3-페닐페닐)플루오렌, 비스(p-톨릴술포닐옥시-3-메틸페닐)디페닐메탄, 비스(p-톨릴술포닐옥시-3,5-디메틸페닐)디페닐메탄, 비스(p-톨릴술포닐옥시-3-프로페닐페닐)디페닐메탄, 비스(p-톨릴술포닐옥시-3-플루오로페닐)디페닐메탄, 비 스(p-톨릴술포닐옥시-3,5-디플루오로페닐)디페닐메탄, 9,9-비스(p-톨릴술포닐옥시-3-플루오로페닐)플루오렌, 9,9-비스(p-톨릴술포닐옥시-3,5-디플루오로페닐)플루오렌, 비스(p-톨릴술포닐옥시페닐)메탄, 비스(p-톨릴술포닐옥시-3-메틸페닐)메탄, 비스(p-톨릴술포닐옥시-3,5-디메틸페닐)메탄, 비스(p-톨릴술포닐옥시-3-프로페닐페닐)메탄, 비스(p-톨릴술포닐옥시페닐)트리플루오로메틸페닐메탄, 비스(p-톨릴술포닐옥시페닐)페닐메탄 등을 들 수 있다. 본 발명에서는, 상기 화학식 20으로 표시되는 화합물 20을 2종 이상 공중합시킬 수도 있다.
본 발명에서는, 상기 화학식 20으로 표시되는 화합물 20의 1종 이상과, 하기 화학식 27 및 화학식 28로 표시되는 화합물로 이루어지는 군에서 선택되는 1종 이상을 공중합시킬 수도 있다.
화학식 27 중, R10 및 R11은 각각 독립적으로 탄소수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소수 1 내지 20의 알콕실기, 아릴기 또는 할로겐 원자를 나타내고, R33 및 R34는 -OSO2Z(여기서, Z는 알킬기, 할로겐화 알킬기 또는 아릴기를 나타냄), 염소 원자, 브롬 원자 또는 요오드 원자를 나타내고, Y는 -O-, -CO-, -COO-, -CONH-, -S-, -SO2- 및 페닐렌기의 군에서 선택된 1종 이상을 나타내고, e 는 0 또는 1을 나타내고, q 및 r은 0 내지 4의 정수를 나타낸다.
상기 화학식 27에서, R10 및 R11 중, 할로겐 원자로는 불소 원자 등을 들 수 있고, 유기기로는, 알킬기로서 메틸기, 에틸기 등을, 할로겐화 알킬기로서 트리플루오로메틸기, 펜타플루오로에틸기 등을, 알릴기로서 프로페닐기 등을, 아릴기로서 페닐기, 펜타플루오로페닐기 등을 들 수 있다. 또한, R33 및 R34 중의 -OSO2Z를 구성하는 Z로는, 알킬기로서 메틸기, 에틸기 등을, 할로겐화 알킬기로서 트리플루오로메틸기 등을, 아릴기로서 페닐기, p-톨릴기, p-플루오로페닐기 등을 들 수 있다.
상기 화학식 27로 표시되는 화합물로는, 예를 들면 4,4'-디메틸술포닐옥시비페닐, 4,4'-디메틸술포닐옥시-3,3'-디프로페닐비페닐, 4,4'-디브로모비페닐, 4,4'-디요오도비페닐, 4,4'-디메틸술포닐옥시-3,3'-디메틸비페닐, 4,4'-디메틸술포닐옥시-3,3'-디플루오로비페닐, 4,4'-디메틸술포닐옥시-3,3',5,5'-테트라플루오로비페닐, 4,4'-디브로모옥타플루오로비페닐, 4,4-메틸술포닐옥시옥타플루오로비페닐, 3,3'-디알릴-4,4'-비스(4-플루오로벤젠술포닐옥시)비페닐, 4,4'-디클로로-2,2'-트리플루오로메틸비페닐, 4,4'-디브로모-2,2'-트리플루오로메틸비페닐, 4,4'-디요오도-2,2'-트리플루오로메틸비페닐, 비스(4-클로로페닐)술폰, 4,4'-디클로로벤조페논, 2,4-디클로로벤조페논 등을 들 수 있다. 상기 화학식 27로 표시되는 화합물은 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다.
화학식 28 중, R12는 탄소수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소수 1 내지 20의 알콕실기, 아릴기 또는 할로겐 원자를 나타내고, R35 및 R36은 -OSO2Z(여기서, Z는 알킬기, 할로겐화 알킬기 또는 아릴기를 나타냄), 염소 원자, 브롬 원자 또는 요오드 원자를 나타내고, s는 0 내지 4의 정수를 나타낸다.
상기 화학식 28에서, R12 중 할로겐 원자로는 불소 원자 등을 나타내고, 유기기로는, 알킬기로서 메틸기, 에틸기 등을, 할로겐화 알킬기로서 트리플루오로메틸기, 펜타플루오로에틸기 등을, 알릴기로서 프로페닐기 등을, 아릴기로서 페닐기, 펜타플루오로페닐기 등을 들 수 있다. 또한, R35 및 R36 중의 -OSO2Z를 구성하는 Z로는, 알킬기로서 메틸기, 에틸기 등을, 할로겐화 알킬기로서 트리플루오로메틸기 등을, 아릴기로서 페닐기, p-톨릴기, p-플루오로페닐기 등을 들 수 있다.
상기 화학식 28로 표시되는 화합물로는, 예를 들면 o-디클로로벤젠, o-디브로모벤젠, o-디요오도벤젠, o-디메틸술포닐옥시벤젠, 2,3-디클로로톨루엔, 2,3-디브로모톨루엔, 2,3-디요오도톨루엔, 3,4-디클로로톨루엔, 3,4-디브로모톨루엔, 3,4-디요오도톨루엔, 2,3-디메틸술포닐옥시벤젠, 3,4-디메틸술포닐옥시벤젠, m-디 클로로벤젠, m-디브로모벤젠, m-디요오도벤젠, m-디메틸술포닐옥시벤젠, 2,4-디클로로톨루엔, 2,4-디브로모톨루엔, 2,4-디요오도톨루엔, 3,5-디클로로톨루엔, 3,5-디브로모톨루엔, 3,5-디요오도톨루엔, 2,6-디클로로톨루엔, 2,6-디브로모톨루엔, 2,6-디요오도톨루엔, 3,5-디메틸술포닐옥시톨루엔, 2,6-디메틸술포닐옥시톨루엔, 2,4-디클로로벤조트리플루오라이드, 2,4-디브로모벤조트리플루오라이드, 2,4-디요오도벤조트리플루오라이드, 3,5-디클로로벤조트리플루오라이드, 3,5-디브로모트리플루오라이드, 3,5-디요오도벤조트리플루오라이드, 1,3-디브로모-2,4,5,6-테트라플루오로벤젠, 2,4-디클로로벤질알코올, 3,5-디클로로벤질알코올, 2,4-디브로모벤질알코올, 3,5-디브로모벤질알코올, 3,5-디클로로페놀, 3,5-디브로모페놀, 3,5-디클로로-t-부톡시카르보닐옥시페닐, 3,5-디브로모-t-부톡시카르보닐옥시페닐, 2,4-디클로로벤조산, 3,5-디클로로벤조산, 2,4-디브로모벤조산, 3,5-디브로모벤조산, 2,4-디클로로벤조산메틸, 3,5-디클로로벤조산메틸, 3,5-디브로모벤조산메틸, 2,4-디브로모벤조산메틸, 2,4-디클로로벤조산-t-부틸, 3,5-디클로로벤조산-t-부틸, 2,4-디브로모벤조산-t-부틸, 3,5-디브로모벤조산-t-부틸 등을 들 수도 있으며, 바람직하게는 m-디클로로벤젠, 2,4-디클로로톨루엔, 3,5-디메틸술포닐옥시톨루엔, 2,4-디클로로벤조트리플루오라이드, 2,4-디클로로벤조페논, 2,4-디클로로페녹시벤젠 등이다. 상기 화학식 28로 표시되는 화합물은 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다.
화합물 5 중의 반복 구조 단위의 비율은, 상기 화학식 5에 있어서 f는 5 내지 100 몰%, 바람직하게는 5 내지 95 몰%, g는 0 내지 95 몰%, 바람직하게는 0 내지 90 몰%, h는 0 내지 95 몰%, 바람직하게는 0 내지 90 몰%(단, f+g+h=100 몰%)이다. f가 5 몰% 미만(g 또는 h가 95 몰%를 초과함)이면, 중합체의 유기 용제에의 용해성이 열화되는 경우가 있다.
화합물 5를 제조할 때 사용되는 촉매로는 전이 금속 화합물을 포함하는 촉매계가 바람직하고, 이러한 촉매계로는, (I) 전이 금속염 및 배위자, 또는 배위자가 배위된 전이 금속(염), 및 (II) 환원제를 필수 성분으로 하고, 또한 중합 속도를 높이기 위해서 「염」을 첨가할 수도 있다. 여기서, 전이 금속염으로는 염화니켈, 브롬화니켈, 요오드화니켈, 니켈 아세틸아세토네이트 등의 니켈 화합물, 염화팔라듐, 브롬화팔라듐, 요오드화팔라듐 등의 팔라듐 화합물, 염화철, 브롬화철, 요오드화철 등의 철 화합물, 염화코발트, 브롬화코발트, 요오드화코발트 등의 코발트 화합물 등을 들 수 있다. 이들 중, 특히 염화니켈, 브롬화니켈 등이 바람직하다.
또한, 배위자로는 트리페닐포스핀, 2,2'-비피리딘, 1,5-시클로옥타디엔, 1,3-비스(디페닐포스피노)프로판 등을 들 수 있지만, 트리페닐포스핀, 2,2'-비피리딘이 바람직하다. 상기 배위자는 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다. 또한, 미리 배위자가 배위된 전이 금속(염)으로는, 예를 들면 염화니켈 2-트리페닐포스핀, 브롬화니켈 2-트리페닐포스핀, 요오드화니켈 2-트리페닐포스핀 및 질산니켈 2-트리페닐포스핀, 염화니켈 2,2'-비피리딘, 브롬화니켈 2,2'-비피리딘, 요오드화니켈 2,2'-비피리딘, 질산니켈 2,2'-비피리딘, 비스(1,5-시클로옥타디엔)니켈, 테트라키스(트리페닐포스핀)니켈, 테트라키스(트리페닐포스파이트)니켈, 테트라키스(트리페닐포스핀)팔라듐 등을 들 수 있지만, 염화니켈 2-트리페닐포스핀 및 염화니켈 2,2'-비피리딘이 바람직하다.
상기 촉매계에서 사용할 수 있는 환원제로는, 예를 들면 철, 아연, 망간, 알루미늄, 마그네슘, 나트륨, 칼슘 등을 들 수 있지만, 아연 및 망간이 바람직하다. 이들 환원제는 산이나 유기산에 접촉시킴으로써 보다 활성화하여 사용할 수 있다. 또한, 이러한 촉매계에서 사용할 수 있는 「염」으로는, 불화나트륨, 염화나트륨, 브롬화나트륨, 요오드화나트륨, 황산나트륨 등의 나트륨 화합물, 불화칼륨, 염화칼륨, 브롬화칼륨, 요오드화칼륨, 황산칼륨 등의 칼륨 화합물, 불화테트라에틸암모늄, 염화테트라에틸암모늄, 브롬화테트라에틸암모늄, 요오드화테트라에틸암모늄, 황산테트라에틸암모늄 등의 암모늄 화합물 등을 들 수 있지만, 브롬화나트륨, 요오드화나트륨, 브롬화칼륨, 브롬화테트라에틸암모늄 및 요오드화테트라에틸암모늄이 바람직하다.
이러한 촉매계에서의 각 성분의 사용 비율에 있어서, 전이 금속염 또는 배위자가 배위된 전이 금속(염)은, 상기 화학식 20, 상기 화학식 27 및 상기 화학식 28로 표시되는 화합물의 총량 1 몰에 대하여 통상적으로는 0.0001 내지 10 몰, 바람직하게는 0.01 내지 0.5 몰이다. 0.0001 몰 미만이면, 중합 반응이 충분히 진행되지 않고, 한편 10 몰을 초과하면, 분자량이 저하되는 경우가 있다. 이러한 촉매계에서, 전이 금속염 및 배위자를 이용하는 경우, 이 배위자의 사용 비율은, 전이 금속염 1 몰에 대하여 통상적으로는 0.1 내지 100 몰, 바람직하게는 1 내지 10 몰이다. 0.1 몰 미만이면, 촉매 활성이 불충분해지고, 한편 100 몰을 초과하면, 분자량이 저하되는 문제가 있다. 또한, 촉매계에서의 환원제의 사용 비율은, 상기 화 학식 20으로 표시되는 화합물, 상기 화학식 27로 표시되는 화합물 및 상기 화학식 28로 표시되는 화합물의 총량 1 몰에 대하여 통상적으로는 0.1 내지 100 몰, 바람직하게는 1 내지 10 몰이다. 0.1 몰 미만이면, 중합이 충분히 진행되지 않고, 한편 100 몰을 초과하면, 얻어지는 중합체의 정제가 곤란해지는 경우가 있다.
또한, 촉매계에 「염」을 사용하는 경우, 그의 사용 비율은, 상기 화학식 20으로 표시되는 화합물, 상기 화학식 27로 표시되는 화합물 및 상기 화학식 28로 표시되는 화합물의 총량 1 몰에 대하여 통상적으로는 0.001 내지 100 몰, 바람직하게는 0.01 내지 1 몰이다. 0.001 몰 미만이면, 중합 속도를 올리는 효과가 불충분하고, 한편 100 몰을 초과하면, 얻어지는 중합체의 정제가 곤란해지는 경우가 있다.
본 발명에서 사용할 수 있는 중합 용매로는, 예를 들면 테트라히드로푸란, 시클로헥사논, 디메틸술폭시드, N,N-디메틸포름아미드, N,N-디메틸아세트아미드, 1-메틸-2-피롤리돈, γ-부티로락톤, γ-부틸로락탐 등을 들 수 있고, 테트라히드로푸란, N,N-디메틸포름아미드, N,N-디메틸아세트아미드, 1-메틸-2-피롤리돈이 바람직하다. 이들 중합 용매는, 충분히 건조시킨 후 이용하는 것이 바람직하다. 중합 용매 중, 상기 화학식 20으로 표시되는 화합물, 화학식 27로 표시되는 화합물 및 화학식 28로 표시되는 화합물의 총량의 농도는 통상적으로는 1 내지 100 중량%, 바람직하게는 5 내지 40 중량%이다. 또한, 상기 중합체를 중합할 때의 중합 온도는 통상적으로는 0 내지 200 ℃, 바람직하게는 50 내지 80 ℃이다. 또한, 중합 시간은 통상적으로는 0.5 내지 100 시간, 바람직하게는 1 내지 40 시간이다. 또한, 상기 화합물 5의 폴리스티렌 환산의 중량 평균 분자량은 통상적으로 1,000 내지 1,000,000이다.
3.2.2. 화합물 6
화학식 6으로 표시되는 중합체(이하, 「화합물 6」이라 함)은, 예를 들면 하기 화학식 29 내지 31로 표시되는 화합물을 포함하는 단량체를 촉매계의 존재하에 중합시킴으로써 제조할 수 있다.
화학식 29 중, R10 및 R11은 각각 독립적으로 탄소수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소수 1 내지 20의 알콕실기, 아릴기 또는 할로겐 원자를 나타내고, X는 -CQQ'-(여기서 Q, Q'는 동일하거나 상이할 수도 있고, 할로겐화 알킬기, 알킬기, 수소 원자, 할로겐 원자 또는 아릴기를 나타냄)로 표시되는 기 및 플루오레닐렌기로 이루어지는 군에서 선택되는 1종 이상을 나타내고, o 및 p는 0 내지 4의 정수를 나타내고, R37 및 R38은 수산기, 할로겐 원자 및 -OM'기(M'는 알칼리 금속임)로 이루어지는 군에서 선택되는 1종 이상을 나타낸다.
상기 화학식 29로 표시되는 화합물(단량체)의 구체예로는, 예를 들면 2,2-비스(4-히드록시페닐)헥사플루오로프로판, 비스(4-히드록시페닐)메탄, 비스(4-히드록시페닐)디페닐메탄, 2,2-비스(4-히드록시-3-메틸페닐)헥사플루오로프로판, 2,2-비스(4-히드록시-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(4-히드록시-3,5-디메 틸페닐)헥사플루오로프로판, 2,2-비스(4-히드록시페닐)프로판, 2,2-비스(4-히드록시-3-메틸페닐)프로판, 2,2-비스(4-히드록시-3-프로페닐페닐)프로판, 2,2-비스(4-히드록시-3,5-디메틸페닐)프로판, 2,2-비스(4-히드록시-3-플루오로페닐)프로판, 2,2-비스(4-히드록시-3,5-디플루오로페닐)프로판, 2,2-비스(4-클로로페닐)헥사플루오로프로판, 비스(4-클로로페닐)메탄, 비스(4-클로로페닐)디페닐메탄, 2,2-비스(4-클로로-3-메틸페닐)헥사플루오로프로반, 2,2-비스(4-클로로-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(4-클로로-3,5-디메틸페닐)헥사플루오로프로판, 2,2-비스(4-클로로페닐)프로판, 2,2-비스(4-클로로-3-메틸페닐)프로판, 2,2-비스(4-클로로-3-프로페닐페닐)프로판, 2,2-비스(4-클로로-3,5-디메틸페닐)프로판, 2,2-비스(4-클로로-3-플루오로페닐)프로판, 2,2-비스(4-클로로-3,5-디플루오로페닐)프로판, 2,2-비스(4-클로로페닐)헥사플루오로프로판, 비스(4-브로모페닐)메탄, 비스(4-브로모페닐)디페닐메탄, 2,2-비스(4-브로모-3-메틸페닐)헥사플루오로프로판, 2,2-비스(4-브로모-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(4-브로모-3,5-디메틸페닐)헥사플루오로프로판, 2,2-비스(4-브로모페닐)프로판, 2,2-비스(4-브로모-3-메틸페닐)프로판, 2,2-비스(4-브로모-3-프로페닐페닐)프로판, 2,2-비스(4-브로모-3,5-디메틸페닐)프로판, 2,2-비스(4-브로모-3-플루오로페닐)프로판, 2,2-비스(4-브로모-3,5-디플루오로페닐)프로판, 비스(4-플루오로페닐)메탄, 비스(4-플루오로페닐)디페닐메탄, 2,2-비스(4-플루오로-3-메틸페닐)헥사플루오로프로판, 2,2-비스(4-플루오로-3-프로페닐페닐)헥사플루오로프로판, 2,2-비스(4-플루오로-3,5-디메틸페닐)헥사플루오로프로판, 2,2-비스(4-플루오로페닐)프로판, 2,2-비스(4-플루오로-3-메틸페닐)프 로판, 2,2-비스(4-플루오로-3-프로페닐페닐)프로판, 2.2-비스(4-플루오로-3,5-디메틸페닐)프로판, 2,2-비스(4-플루오로-3-플루오로페닐)프로판, 2,2-비스(4-플루오로-3,5-디플루오로페닐)프로판 등을 들 수 있다. 상기 비스페놀 화합물은 나트륨, 칼륨 등을 함유하는 염기성 화합물에 의해서 수산기를 -0M'기(M'는 알칼리 금속임)로 치환시킬 수도 있다. 본 발명에서는, 상기 화학식 29로 표시되는 화합물을 2종 이상 공중합할 수도 있다.
화학식 30 중, R10 및 R11은 각각 독립적으로 탄소수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소수 1 내지 20의 알콕실기, 아릴기 또는 할로겐 원자를 나타내고, R39 및 R40은 수산기, 할로겐 원자 및 -OM'기(M'는 알칼리 금속임)로 이루어지는 군에서 선택되는 1종 이상을 나타내고, Y는 -O-, -CO-, -COO-, -CONH-, -S-, -SO2- 및 페닐렌기의 군에서 선택된 1종 이상을 나타내고, e는 O 또는 1을 나타내고, q 및 r은 0 내지 4의 정수를 나타낸다.
상기 화학식 30으로 표시되는 화합물로는, 예를 들면 4,4'-디클로로비페닐, 4,4'-디브로모비페닐, 4,4'-디플루오로비페닐, 4,4'-디요오도비페닐, 4,4'-디히드록시비페닐, 4,4'-디히드록시-3,3'-디프로페닐비페닐, 4,4'-디히드록시-3,3'-디메 틸비페닐, 4,4'-디히드록시-3,3'-디에틸비페닐, 4,4'-디메틸히드록시-3,3',5,5'-테트라플루오로비페닐, 4,4'-디브로모옥타플루오로비페닐, 4,4-디히드록시옥타플루오로비페닐, 3,3'-디알릴-4,4'-비스(4-히드록시)비페닐, 4,4'-디클로로 -2,2'-트리플루오로메틸비페닐, 4,4'-디브로모-2,2'-트리플루오로메틸비페닐, 4,4'-디요오도-2,2'-트리플루오로메틸비페닐, 비스(4-클로로페닐)술폰, 비스(4-히드록시페닐)술폰, 비스(4-클로로페닐)에테르, 비스(4-히드록시페닐)에테르, 4,4'-디클로로벤조페논, 4,4'-디히드록시벤조페논, 2,4-디클로로벤조페논, 2,4-디히드록시벤조페논 등을 들 수 있다. 상기 비스페놀 화합물은 나트륨, 칼륨 등을 함유하는 염기성 화합물에 의해서 수산기를 -0M'기(M'는 알칼리 금속임)로 치환시킬 수도 있다. 상기 화학식 30으로 표시되는 화합물은 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다.
화학식 31 중, R12는 탄소수 1 내지 20의 탄화수소기, 시아노기, 니트로기, 탄소수 1 내지 20의 알콕실기, 아릴기 또는 할로겐 원자를 나타내고, R35 및 R36은 -OSO2Z(여기서, Z는 알킬기, 할로겐화 알킬기 또는 아릴기를 나타냄), 염소 원자, 브롬 원자 또는 요오드 원자를 나타내고, s는 0 내지 4의 정수를 나타낸다.
상기 화학식 31로 표시되는 화합물로는, 예를 들면 1,2-디히드록시벤젠, 1,3-디히드록시벤젠, 1,4-디히드록시벤젠, 2,3-디히드록시톨루엔, 2,5-디히드록시톨루엔, 2,6-디히드록시톨루엔, 3,4-디히드록시톨루엔, 3,5-디히드록시톨루엔, o-디클로로벤젠, o-디브로모벤젠, o-디요오도벤젠, o-디메틸술포닐옥시벤젠, 2,3-디클로로톨루엔, 2,3-디브로모톨루엔, 2,3-디요오도톨루엔, 3,4-디클로로톨루엔, 3,4-디브로모톨루엔, 3,4-디요오도톨루엔, 2,3-디메틸술포닐옥시벤젠, 3,4-디메틸술포닐옥시벤젠, m-디클로로벤젠, m-디브로모벤젠, m-디요오도벤젠, m-디메틸술포닐옥시벤젠, 2,4-디클로로톨루엔, 2,4-디브로모톨루엔, 2,4-디요오도톨루엔, 3,5-디클로로톨루엔, 3,5-디브로모톨루엔, 3,5-디요오도톨루엔, 2,6-디클로로톨루엔, 2,6-디브로모톨루엔, 2,6-디요오도톨루엔, 3,5-디메틸술포닐옥시톨루엔, 2,6-디메틸술포닐옥시톨루엔, 2,4-디클로로벤조트리플루오라이드, 2,4-디브로모벤조트리플루오라이드, 2,4-디요오도벤조트리플루오라이드, 3,5-디클로로벤조트리플루오라이드, 3,5-디브로모트리플루오라이드, 3,5-디요오도벤조트리플루오라이드, 1,3-디브로모-2,4,5,6-테트라플루오로벤젠, 2,4-디클로로벤질알코올, 3,5-디클로로벤질알코올, 2,4-디브로모벤질알코올, 3,5-디브로모벤질알코올, 3,5-디클로로페놀, 3,5-디브로모페놀, 3,5-디클로로-t-부톡시카르보닐옥시페닐, 3,5-디브로모-t-부톡시카르보닐옥시페닐, 2,4-디클로로벤조산, 3,5-디클로로벤조산, 2,4-디브로모벤조산, 3,5-디브로모벤조산, 2,4-디클로로벤조산메틸, 3,5-디클로로벤조산메틸, 3,5-디브로모벤조산메틸, 2,4-디브로모벤조산메틸, 2,4-디클로로벤조산-t-부틸, 3,5-디클로로벤조산-t-부틸, 2,4-디브로모벤조산-t-부틸, 3,5-디브로모벤조산-t-부틸 등을 들 수도 있다. 상기 비스페놀 화합물은 나트륨, 칼륨 등을 함유하는 염기성 화합물에 의해서 수산기를 -OM'기(M'는 알칼리 금속임)로 치환시킬 수도 있다. 상기 화학식 31로 표시되는 화합물은 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다. 화학식 6으로 표시되는 화합물 6 중 반복 구조 단위의 비율은, 상기 화학식 6에 있어서 i는 0 내지 100 몰%, j는 0 내지 100 몰%(단, i+j=100 몰%)이다.
화학식 6으로 표시되는 화합물 6의 합성 방법으로는, 예를 들면 비스페놀 화합물과 디할로겐화 화합물을 알칼리 금속 화합물의 존재하에 용제 중에서 가열함으로써 얻어진다. 상기 비스페놀 화합물 및 디할로겐화 화합물의 사용 비율은, 비스페놀 화합물이 45 내지 55 몰%, 바람직하게는 48 내지 52 몰%, 디할로겐화 화합물이 55 내지 45 몰%, 바람직하게는 52 내지 48 몰%이다. 비스페놀 화합물의 사용 비율이 45 몰% 미만이거나 55 몰%를 넘으면 중합체의 분자량이 상승되기 어렵고, 도막의 도포성이 열화되는 경우가 있다. 이때 사용하는 알칼리 금속 화합물로는, 예를 들면 수산화나트륨, 수산화칼륨, 수산화리튬, 탄산나트륨, 탄산칼륨, 탄산리튬, 탄산수소나트륨, 탄산수소칼륨, 탄산수소리튬, 수소화나트륨, 수소화칼륨, 수소화리튬, 금속 나트륨, 금속 칼륨, 금속 리튬 등을 들 수 있다. 이들은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 알칼리 금속 화합물의 사용량은 비스페놀 화합물에 대하여 통상적으로는 100 내지 400 몰%, 바람직하게는 100 내지 250 몰%이다. 또한, 반응을 촉진시키기 위해서, 금속 구리, 염화 제1 구리, 염화 제2 구리, 브롬화 제1 구리, 브롬화 제2 구리, 요오드화 제1 구리, 요오드화 제2 구리, 황산 제1 구리, 황산 제2 구리, 아세트산 제1 구리, 아세트산 제2 구리, 포름산 제1 구리, 포름산 제2 구리 등의 조촉매를 사용할 수도 있다. 상기 조촉매의 사용량은 비스페놀 화합물에 대하여 통상적으로는 1 내지 50 몰%, 바람직하게는 1 내지 30 몰%이다.
반응에 사용되는 용제로는, 예를 들면 피리딘, 퀴놀린, 벤조페논, 디페닐에테르, 디알콕시벤젠(알콕실기의 탄소수는 1 내지 4), 트리알콕시벤젠(알콕실기의 탄소수는 1 내지 4), 디페닐술폰, 디메틸술폭시드, 디메틸술폰, 디에틸술폭시드, 디에틸술폰, 디이소프로필술폰, 테트라히드로푸란, 테트라히드로티오펜, 술포란, N-메틸-2-피롤리돈, N-에틸-2-피롤리돈, 디메틸이미다졸리디논, γ-부티로락톤, 디메틸포름아미드, 디메틸아세트아미드 등을 사용할 수 있다. 이들은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 화학식 6으로 표시되는 화합물 6을 합성할 때, 반응 농도는 단량체의 중량을 기준으로 하여, 2 내지 50 중량%이고, 반응 온도는 50 내지 250 ℃이다. 또한, 중합체 합성시 발생하는 금속염이나 미반응 단량체를 제거하기 위해서, 반응 용액을 여과하는 것이나 반응 용액을 중합체에 대하여 빈용매(poor solvent)인 용매에 의한 재침전, 또는 산성 또는 알칼리성 수용액에 의해 세정하는 것이 바람직하다. 이와 같이 하여 얻어지는 화합물 6의 GPC법에 의한 중량 평균 분자량은 통상적으로는 500 내지 500,000, 바람직하게는 800 내지 100,000이다.
3.2.3. 화합물 7
화학식 7로 표시되는 중합체(이하, 「화합물 7」이라 함)는, 예를 들면 하기 화학식 32 및 화학식 33으로 표시되는 화합물로 이루어지는 군에서 선택되는 1종 이상의 화합물과, 하기 화학식 34 및 화학식 35로 표시되는 화합물로 이루어지는 군에서 선택되는 1종 이상의 화합물을 촉매의 존재하에서 중합함으로써 얻을 수 있다.
(화학식 32 및 33 중, R14 내지 R19 및 k, t, u, v, w는 상기 화학식 8 및 상기 화학식 9에 대하여 정의한 바와 같음);
(화학식 34 및 35 중, R19 내지 R24 및 l, w, x, y, z는 상기 화학식 9 및 상기 화학식 10에 대하여 정의한 바와 같고, X'는 할로겐 원자를 나타냄).
상기 화학식 32로 표시되는 화합물로는, 예를 들면 4,4'-디에티닐비페닐, 3,3'-디에티닐비페닐, 3,4'-디에티닐비페닐, 4,4'-디에티닐디페닐에테르, 3,3'-디에티닐디페닐에테르, 3,4'-디에티닐디페닐에테르, 4,4'-디에티닐벤조페논, 3,3'-디에티닐벤조페논, 3,4'-디에티닐벤조페논, 4,4'-디에티닐디페닐메탄, 3,3'-디에티닐디페닐메탄, 3,4'-디에티닐디페닐메탄, 4,4'-디에티닐벤조산페닐에스테르, 3,3'-디에티닐벤조산페닐에스테르, 3,4'-디에티닐벤조산페닐에스테르, 4,4'-디에티닐벤즈아닐리드, 3,3'-디에티닐벤즈아닐리드, 3,4'-디에티닐벤즈아닐리드, 4,4'-디에티닐디페닐술피드, 3,3'-디에티닐디페닐술피드, 3,4'-디에티닐디페닐술피드, 4,4'-디에티닐디페닐술폰, 3,3'-디에티닐디페닐술폰, 3,4'-디에티닐디페닐술폰, 2,4,4'-트리에티닐디페닐에테르, 9,9-비스(4-에티닐페닐)플루오렌, 4,4"-디에티닐-p-터페닐, 4,4"-디에티닐-m-터페닐, 4,4"-디에티닐-o-터페닐 등을 들 수 있다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
상기 화학식 33으로 표시되는 화합물로는, 예를 들면 1,2-디에티닐벤젠, 1,3-디에티닐벤젠, 1,4-디에티닐벤젠, 2,5-디에티닐톨루엔, 3,4-디에티닐톨루엔 등을 들 수 있다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
상기 화학식 34로 표시되는 화합물로는, 예를 들면 1,2-비스(2-브로모페녹 시)벤젠, 1,2-비스(2-요오도페녹시)벤젠, 1,2-비스(3-브로모페녹시)벤젠, 1,2-비스(3-요오도페녹시)벤젠, 1,2-비스(4-브로모페녹시)벤젠, 1,2-비스(4-요오도페녹시)벤젠, 1,3-비스(2-브로모페녹시)벤젠, 1,3-비스(2-요오도페녹시)벤젠, 1,3-비스(3-브로모페녹시)벤젠, 1,3-비스(3-요오도페녹시)벤젠, 1,3-비스(4-브로모페녹시)벤젠, 1,3-비스(4-요오도페녹시)벤젠, 1,4-비스(3-브로모페녹시)벤젠, 1,4-비스(3-요오도페녹시)벤젠, 1,4-비스(2-브로모페녹시)벤젠, 1,4-비스(2-요오도페녹시)벤젠, 1,4-비스(4-브로모페녹시)벤젠, 1,4-비스(4-요오도페녹시)벤젠, 1-(2-브로모벤조일)-3-(2-브로모페녹시)벤젠, 1-(2-요오도벤조일)-3-(2-요오도페녹시)벤젠, 1-(3-브로모벤조일)-3-(3-브로모페녹시) 벤젠, 1-(3-요오도벤조일)-3-(3-요오도페녹시)벤젠, 1-(4-브로모벤조일)-3-(4-브로모페녹시)벤젠, 1-(4-요오도벤조일)-3-(4-요오도페녹시)벤젠, 1-(3-브로모벤조일)-4-(3-브로모페녹시)벤젠, 1-(3-요오도벤조일)-4-(3-요오도페녹시)벤젠, 1-(4-브로모벤조일)-4-(4-브로모페녹시)벤젠, 1-(4-요오도벤조일)-4-(4-요오도페녹시)벤젠, 2,2'-비스(2-브로모페녹시)벤조페논, 2,2'-비스(2-요오도페녹시)벤조페논, 2,4'-비스(2-브로모페녹시)벤조페논, 2,4'-비스(2-요오도페녹시)벤조페논, 4,4'-비스(2-브로모페녹시)벤조페논, 4,4'-비스(2-요오도페녹시)벤조페논, 2,2'-비스(3-브로모페녹시)벤조페논, 2,2'-비스(3-요오도페녹시)벤조페논, 2,4'-비스(3-브로모페녹시)벤조페논, 2,4'-비스(3-요오도페녹시)벤조페논, 4,4'-비스(3-브로모페녹시)벤조페논, 4,4'-비스(3-요오도페녹시)벤조페논, 2,2'-비스(4-브로모페녹시)벤조페논, 2,2'-비스(4-요오도페녹시)벤조페논, 2,4'-비스(4-브로모페녹시)벤조페논, 2,4'-비스(4-요오도페녹시)벤조페논, 4,4'-비스(4-브로모페 녹시)벤조페논, 4,4'-비스(4-요오도페녹시)벤조페논, 2,2'-비스(2-브로모벤조일)벤조페논, 2,2'-비스(2-요오도벤조일)벤조페논, 2,4'-비스(2-브로모벤조일)벤조페논, 2,4'-비스(2-요오도벤조일)벤조페논, 4,4'-비스(2-브로모벤조일)벤조페논, 4,4'-비스(2-요오도벤조일)벤조페논, 2,2'-비스(3-브로모벤조일)벤조페논, 2,2'-비스(3-요오도벤조일)벤조페논, 2,4'-비스(3-브로모벤조일)벤조페논, 2,4'-비스(3-요오도벤조일)벤조페논, 4,4'-비스(3-브로모벤조일)벤조페논, 4,4'-비스(3-요오도벤조일)벤조페논, 2,2'-비스(4-브로모벤조일)벤조페논, 2,2'-비스(4-요오도벤조일)벤조페논, 2,4'-비스(4-브로모벤조일)벤조페논, 2,4'-비스(4-요오도벤조일)벤조페논, 4,4'-비스(4-브로모벤조일)벤조페논, 4,4'-비스(4-요오도벤조일)벤조페논, 3,4'-비스(2-브로모페녹시)디페닐에테르, 3,4'-비스(2-요오도페녹시)디페닐에테르, 3,4'-비스(3-브로모페녹시)디페닐에테르, 3,4'-비스(3-요오도페녹시)디페닐에테르, 3,4'-비스(4-브로모페녹시)디페닐에테르, 3,4'-비스(4-요오도페녹시)디페닐에테르, 4,4'-비스(2-브로모페녹시)디페닐에테르, 4,4'-비스(2-요오도페녹시)디페닐에테르, 4,4'-비스(3-브로모페녹시)디페닐에테르, 4,4'-비스(3-요오도페녹시)디페닐에테르, 4,4'-비스(4-브로모페녹시)디페닐에테르, 4,4'-비스(4-요오도페녹시)디페닐에테르, 3,4'-비스(2-브로모벤조일)디페닐에테르, 3,4'-비스(2-요오도벤조일)디페닐에테르, 3,4'-비스(3-브로모벤조일)디페닐에테르, 3,4'-비스(3-요오도벤조일)디페닐에테르, 3,4'-비스(4-브로모벤조일)디페닐에테르, 3,4'-비스(4-요오도벤조일)디페닐에테르, 4,4'-비스(2-브로모벤조일)디페닐에테르, 4,4'-비스(2-요오도벤조일)디페닐에테르, 4,4'-비스(3-브로모벤조일)디페닐에테르, 4,4'-비스(3-요오도벤조일)디페닐에테르, 4,4'-비스(4-브로모벤조일)디페닐에테르, 4,4'-비스(4-요오도벤조일)디페닐에테르, 2,2'-비스(4-클로로페닐)디페닐메틸리덴, 2,2'-비스(4-요오도페닐)디페닐메틸리덴, 2,2'-비스(4-브로모페닐)디페닐메틸리덴, 2,2'-비스(3-클로로페닐)디페닐메틸리덴, 2,2'-비스(3-요오도페닐)디페닐메틸리덴, 2,2'-비스(3-브로모페닐)디페닐메틸리덴, 9,9-비스(4-클로로페닐)플루오렌, 9,9-비스(4-요오도페닐)플루오렌, 9,9-비스(4-브로모페닐)플루오렌, 9,9-비스(3-클로로페닐)플루오렌, 9,9-비스(3-요오도페닐)플루오렌, 9,9-비스(3-브로모페닐)플루오렌, 4,4"-디클로로-m-터페닐, 4,4"-디요오도-m-터페닐, 4,4"-디브로모-m-터페닐, 4,4"-디클로로-p-터페닐, 4,4"-디요오도-p-터페닐 및 4,4"-디브로모-p-터페닐 등을 들 수 있다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
상기 화학식 35로 표시되는 화합물로는, 예를 들면 1,2-디클로로벤젠, 1,3-디클로로벤젠, 1,4-디클로로벤젠, 1,2-디요오도벤젠, 1,3-디요오도벤젠, 1,4-디요오도벤젠, 1,2-디브로모벤젠, 1,3-디브로모벤젠, 1,4-디브로모벤젠, 2,3-디클로로톨루엔, 2,4-디클로로톨루엔, 2,5-디클로로톨루엔, 2,6-디클로로톨루엔, 3,4-디클로로톨루엔, 2,3-디요오도톨루엔, 2,4-디요오도톨루엔, 2,5-디요오도톨루엔, 2,6-디요오도톨루엔, 3,4-디요오도톨루엔, 2,3-디브로모톨루엔, 2,4-디브로모톨루엔, 2,5-디브로모톨루엔, 2,6-디브로모톨루엔, 3,4-디브로모톨루엔 등을 들 수 있다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다.
본 발명에서, 화합물 7은, 상기 화학식 32로 표시되는 화합물 및(또는) 화학식 33으로 표시되는 화합물과, 상기 화학식 34로 표시되는 화합물 및(또는) 화학식 35로 표시되는 화합물을 촉매의 존재하에서 중합시킴으로써 제조되고, 이때 상기 화학식 32로 표시되는 화합물 및(또는) 화학식 33으로 표시되는 화합물과, 상기 화학식 34로 표시되는 화합물 및(또는) 화학식 35로 표시되는 화합물의 사용 비율에 있어서, 후자의 화합물의 총량은 전자의 화합물의 총량 1 몰에 대하여 0.8 내지 1.2 몰, 바람직하게는 0.9 내지 1.1 몰, 특히 바람직하게는 0.95 내지 1.05 몰이다. 후자의 화합물의 총량이 0.8 몰 미만인 경우나 1.2 몰을 초과하는 경우, 얻어지는 중합체의 분자량이 상승되기 어렵다.
화합물 7의 제조에서는, 상기 화학식 32 내지 35로 표시되는 화합물을, 전이 금속 화합물을 포함하는 촉매의 존재하에서 중합시키는 것이 바람직하다. 또한, 전이 금속 화합물 및 염기성 화합물을 포함하는 촉매가 보다 바람직하고, 특히 하기의 (a) 성분, (b) 성분 및 (c) 성분으로 구성되는 것이 특히 바람직하다:
(a) 팔라듐염 및 팔라듐에 대하여 배위자로서 결합하거나, 배위자로서 결합하는 기(원자단)를 공급하여 착체(착 이온을 포함함)를 형성할 수 있는 물질(이하, 배위자 형성체라 함), 또는 팔라듐 착체(필요에 따라서 배위자 형성체를 더 첨가할 수도 있음),
(b) 1가의 구리 화합물, 및
(c) 염기성 화합물.
(a) 성분 중 팔라듐염으로는, 예를 들면 염화팔라듐, 브롬화팔라듐, 요오드화팔라듐 등을 들 수 있다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 여기서, 팔라듐염의 사용 비율은 상기 화학식 32 내지 35로 표시 되는 화합물의 총량 1 몰에 대하여 바람직하게는 0.0001 내지 10 몰, 더욱 바람직하게는 0.001 내지 1 몰이다. 0.0001 몰 미만이면 중합이 충분히 진행되지 못하는 경우가 있고, 한편 10 몰을 초과하면 정제가 곤란해지는 경우가 있다.
(a) 성분 중 배위자 형성체로는, 예를 들면 트리페닐포스핀, 트리-o-톨릴포스핀, 트리시아노페닐포스핀, 트리시아노메틸포스핀 등을 들 수 있다. 그 중에서도, 트리페닐포스핀이 바람직하다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 배위자 형성체의 사용 비율은, 상기 화학식 32 내지 35로 표시되는 화합물의 총량 1 몰에 대하여 바람직하게는 0.0004 내지 50 몰, 더욱 바람직하게는 0.004 내지 5 몰이다. 0.0004 몰 미만이면 중합이 충분히 진행되지 못하는 경우가 있고, 한편 50 몰을 초과하면 정제가 곤란해지는 경우가 있다.
(a) 성분 중 팔라듐 착체로는, 예를 들면 디클로로비스(트리페닐포스핀)팔라듐, 디브로모비스(트리페닐포스핀)팔라듐, 디요오도비스(트리페닐포스핀)팔라듐, 디클로로비스(트리-o-톨릴포스핀)팔라듐, 디클로로비스(트리시아노페닐포스핀)팔라듐, 디클로로비스(트리시아노메틸포스핀)팔라듐, 디브로모비스(트리-o-톨릴포스핀)팔라듐, 디브로모비스(트리시아노페닐포스핀)팔라듐, 디브로모비스(트리시아노메틸포스핀)팔라듐, 디요오도비스(트리-o-톨릴포스핀)팔라듐, 디요오도비스(트리시아노페닐포스핀)팔라듐, 디요오도비스(트리시아노메틸포스핀)팔라듐, 테트라키스(트리페닐포스핀)팔라듐, 테트라키스(트리-o-톨릴포스핀)팔라듐, 테트라키스(트리시아노페닐포스핀)팔라듐, 테트라키스(트리시아노메틸포스핀)팔라듐 등을 들 수 있다. 그 중에서도 디클로로비스(트리페닐포스핀)팔라듐, 테트라키스(트리페닐포스핀)팔 라듐이 바람직하다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 여기서, 팔라듐 착체의 사용 비율은, 상기 화학식 32 내지 35로 표시되는 화합물의 총량 1 몰에 대하여 바람직하게는 0.0001 내지 10 몰, 더욱 바람직하게는 0.001 내지 1 몰이다. 0.0001 몰 미만이면 중합이 충분히 진행되지 못하는 경우가 있는 한편, 10 몰을 초과하면 정제가 곤란해지는 경우가 있다.
(b) 1가의 구리 화합물로는, 예를 들면 염화 구리(I), 브롬화 구리(I), 요오드화 구리(I) 등을 들 수 있다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 여기서, (b) 1가의 구리 화합물의 사용 비율은, 상기 화학식 32 내지 35로 표시되는 화합물의 총량 1 몰에 대하여 바람직하게는 0.0001 내지 10 몰, 더욱 바람직하게는 0.001 내지 1 몰이다. 0.0001 몰 미만이면 중합이 충분히 진행되지 못하는 경우가 있는 한편, 10 몰을 초과하면 정제가 곤란해지는 경우가 있다.
(c) 염기성 화합물로는, 예를 들면 피리딘, 피롤, 피페라진, 피롤리딘, 피페리딘, 피콜린, 트리메틸아민, 트리에틸아민, 모노에탄올아민, 디에탄올아민, 디메틸모노에탄올아민, 모노메틸디에탄올아민, 트리에탄올아민, 디아자비시클로옥탄, 디아자비시클로노난, 디아자비시클로운데센, 테트라메틸암모늄히드록시드, 디에틸아민, 암모니아, n-부틸아민, 이미다졸 등을 들 수 있다. 그 중에서도 디에틸아민, 피페리딘, n-부틸아민이 바람직하다. 이들 화합물은 1종 단독으로 또는 2종 이상을 동시에 사용할 수 있다. 여기서, (c) 염기성 화합물의 사용 비율은, 상기 화학식 32 내지 35로 표시되는 화합물의 총량 1 몰에 대하여 바람직하게는 1 내지 1000 몰, 더욱 바람직하게는 1 내지 100 몰이다. 1 몰 미만이면 중합이 충분히 진행되지 못하는 경우가 있는 한편, 100 몰을 초과하면 경제적이다.
3.2.4. 화합물 8
화학식 11로 표시되는 중합체(이하, 「화합물 8」이라 함)는, 예를 들면 하기 화학식 36과 하기 화학식 37 및 38로 표시되는 화합물을 반응시킴으로써 제조할 수 있다.
화학식 36 내지 38 중, R13 및 R13'는 수소 원자 또는 상기 화학식 12 및 13으로 표시되는 방향족기의 군에서 선택되는 1종 이상의 기를 나타내고, W1 및 W2는 상기 화학식 14 및 15로 표시되는 2가의 방향족기로 이루어지는 군에서 선택되는 1종 이상의 기를 나타낸다.
화학식 11로 표시되는 화합물 8은 화학식 36의 시클로펜타디에논기와 화학식 37 및 38의 아세틸렌기를 딜즈-알더(Diels-Alder) 반응시킴으로써 얻을 수 있다.
화합물 8의 수평균 분자량(Mn)은 3,500 초과, 바람직하게는 4,000 초과이며, 바람직하게는 6,400 미만, 보다 바람직하게는 6,000 미만이다. 또한, 화합물 8의 중량 평균 분자량(Mw)은 500 초과, 바람직하게는 8,000 초과이며, 바람직하게는 15,000 미만, 보다 바람직하게는 12,000 미만이다. 또한, 화합물 8은 바람직하게는 약 2.5 미만, 보다 바람직하게는 약 2.3 미만의 다분산성(Mw/Mn)을 갖는다.
3.2.5. 화합물 9
화학식 16으로 표시되는 중합체(이하, 「화합물 9」라 함)은 이하의 화학식 39 내지 41의 화합물을 반응시킴으로써 얻어진다.
(화학식 39 중, X는 상술한 화학식 17로부터 선택된 하나의 구조를 나타냄);
(화학식 40 중, Y는 상술한 화학식 18 또는 19로부터 선택된 하나의 구조를 나타냄).
화학식 39로 표시되는 화합물로는, 예를 들면 2,4-디아미노레조르시놀, 4,6-디아미노레조르시놀, 2,2-비스(3-아미노-4-히드록시페닐)프로판, 2,2-비스(4-아미노-3-히드록시페닐)프로판, 3,3'-디아미노-4,4'-디히드록시비페닐술폰, 4,4'-디아미노-3,3'-디히드록시비페닐술폰, 3,3'-디아미노-4,4'-디히드록시비페닐, 4,4'-디아미노-3,3'-디히드록시비페닐, 9,9-비스-{4-((4-아미노-3-히드록시)페녹시)페닐}플루오렌, 9,9-비스-{4-((3-아미노-4-히드록시)페녹시)페닐}플루오렌, 9,9-비스-{4-((4-아미노-3-히드록시)페녹시-3-페닐)페닐}플루오렌, 9,9-비스-{4-((3-아미노-4-히드록시)페녹시-3-페닐)페닐}플루오렌, 3,3'-디아미노-4,4'-디히드록시디페닐에테르, 4,4'-디아미노-3,3'-디히드록시디페닐에테르 등을 들 수 있지만, 반드시 이들로 한정되는 것은 아니다. 또한, 이들 2종 이상의 디아미노페놀 화합물을 조합하여 사용하는 것도 가능하다.
화학식 40으로 표시되는 화합물로는, 예를 들면 4-메틸이소프탈산, 4-페닐이소프탈산, 4-t-부틸이소프탈산, 4-트리메틸실릴이소프탈산, 4-아다만틸이소프탈산, 5-메틸이소프탈산, 5-페닐이소프탈산, 5-t-부틸이소프탈산, 5-트리메틸실릴이소프탈산, 5-아다만틸이소프탈산, 2-메틸테레프탈산, 2-페닐테레프탈산, 2-t-부틸테레프탈산, 2-트리메틸실릴테레프탈산, 2-아다만틸테레프탈산, 4,4'-비스(2-메틸)페닐 디카르복실산, 4,4'-비스(3-메틸)페닐디카르복실산, 4,4'-비스(2-t-부틸)페닐디카르복실산, 4,4'-비스(3-t-부틸)페닐디카르복실산, 4,4'-비스(2-트리메틸실릴)페닐디카르복실산, 4,4'-비스(3-트리메틸실릴)페닐디카르복실산, 4,4'-비스(2-아다만틸)페닐디카르복실산, 4,4'-비스(3-아다만틸)페닐디카르복실산, 6-메틸나프탈렌-1,4-디카르복실산, 6-t-부틸나프탈렌-1,4-디카르복실산, 6-트리메틸실릴나프탈렌-1,4-디카르복실산, 6-아다만틸나프탈렌-1,4-디카르복실산, 4-메틸나프탈렌-2,6-디카르복실산, 4-t-부틸나프탈렌-2,6-디카르복실산, 4-트리메틸실릴나프탈렌-2,6-디카르복실산, 4-아다만틸나프탈렌-2,6-디카르복실산 등을 들 수 있지만, 반드시 이들로 한정되는 것은 아니다. 또한, 이들 화합물 중 2종 이상을 조합하여 사용하는 것도 가능하다.
본 발명에서 사용되는 화학식 41로 표시되는 구조를 포함하는 디카르복실산으로는, 예를 들면 1,3-아다만탄디카르복실산, 2,5-디메틸아다만탄-1,3-디카르복실산, 2,5-디페닐아다만탄-1,3-디카르복실산, 2,5-비스(t-부틸)아다만탄-1,3-디카르복실산 등을 들 수 있지만, 반드시 이들로 한정되는 것은 아니다. 또한, 이들 화합물 중 2종 이상을 조합하여 사용하는 것도 가능하다.
화합물 9의 제조 방법으로는, 공지된 산 클로라이드법, 활성 에스테르법, 폴리인산이나 디시클로헥실카르보디이미드 등의 탈수 축합제의 존재하에서의 축합 반응에 의한 합성 방법 등에 의해 얻을 수 있다.
본 발명에 있어서, 화학식 39로 표시되는 디아미노페놀 화합물(M 몰)과, 화학식 40으로 표시되는 디카르복실산(N 몰)과의 몰비(N/M)가 0.5 내지 0.9인 범위에서 반응시켜 분지된 구조를 갖는 중합체를 얻는 것이 바람직하다. 몰비(N/M)가 0.9보다 크면, 디카르복실산의 부피가 큰 치환기에 의한 저유전율화 효과가 낮아질 우려가 있고, 또한 몰비(N/M)가 0.5보다 작으면, 얻어지는 중합체의 분자량이 상승되지 않고, 미반응의 디아미노페놀 화합물이 잔존하여, 유기 절연막의 막 형성에 있어서 문제가 발생하거나, 또는 취약한 유기 절연막이 얻어질 우려가 있다.
중합 방법의 일례로서, 산 클로라이드법에 의해 중합체를 제조하는 경우를 설명한다. 예를 들면, N,N-디메틸포름아미드 등의 촉매 존재하에서, 화학식 40으로 표시되는 디카르복실산, 예를 들면 5-t-부틸이소프탈산과 과잉량의 염화티오닐을 실온 내지 75 ℃에서 반응시키고, 과잉 염화티오닐을 가열 및 감압에 의해 증류 제거한 후, 잔류물을 헥산 등의 용매로 재결정시킴으로써 5-t-부틸이소프탈산클로라이드가 얻어진다. 이어서, 화학식 39로 표시되는 디아미노페놀 화합물, 예를 들면 2,2-비스(3-아미노-4-히드록시페닐)프로판을 통상적으로 N-메틸-2-피롤리돈, N,N-디메틸아세트아미드 등의 극성 용매에 용해시키고, 이를 미리 제조한 상기 디카르복실산의 클로라이드 화합물과 트리에틸아민 등의 산 수용제 존재하에서 실온 내지 -30 ℃에서 반응시킴으로써, 화학식 16으로 표시되는 폴리벤조옥사졸 전구체를 주 구조로 하는, 중합체를 포함하는 화합물 9를 얻을 수 있다.
또한, 상기 산 클로라이드 화합물 대신에 화학식 40으로 표시되는 디카르복실산 화합물의 활성 에스테르 화합물을 디아미노페놀 화합물과 반응시킴으로써도 화합물 9를 얻을 수 있다.
본 발명의 유기계 절연막을 위한 막 형성용 조성물의 형성 공정에서는, 필요에 따라서 용매를 사용할 수 있다. 중합 용매로는 특별히 제한은 없지만, 예를 들면 클로로포름, 디클로로메탄, 1,2-디클로로에탄, 클로로벤젠, 디클로로벤젠 등의 할로겐계 용매; 벤젠, 톨루엔, 크실렌, 메시틸렌, 디에틸벤젠 등의 방향족 탄화수소계 용매; 디에틸에테르, 테트라히드로푸란, 디옥산, 디글라임, 아니솔, 디에틸렌글리콜 디메틸에테르, 디에틸렌글리콜 디에틸에테르, 디에틸렌글리콜 메틸에틸에테르 등의 에테르계 용매; 아세톤, 메틸에틸케톤, 2-헵타논, 시클로헥사논 및 시클로펜타논 등의 케톤계 용매; 아세트산메틸, 아세트산에틸, 아세트산프로필, 아세트산부틸, 락트산메틸, 락트산에틸, 락트산부틸, γ-부티로락톤 등의 에스테르계 용매; N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸-2-피롤리돈 등의 아미드계 용매 등을 들 수 있다. 이들 용매는 충분히 건조 및 탈산소하여 사용하는 것이 바람직하다. 이들 용매는 1종 단독으로 사용하거나, 2종 이상을 동시에 사용할 수 있다. 중합 용매 중에서의 단량체(중합 성분) 농도는 바람직하게는 1 내지 80 중량%, 더욱 바람직하게는 5 내지 60 중량%이다. 또한, 중합 온도는 바람직하게는 0 내지 150 ℃, 더욱 바람직하게는 5 내지 100 ℃이다. 또한, 중합 시간은 바람직하게는 0.5 내지 100 시간, 더욱 바람직하게는 1 내지 40 시간이다.
본 발명에 있어서, 유기계 절연막을 형성하기 위해서는, 상기 화합물 5 내지 9의 군으로부터 선택되는 1종 이상의 중합체를 유기 용제에 용해시켜 조성물 3을 얻고, 이 조성물 3을 기판에 도포하여 도막을 형성하고, 이 도막을 가열한다. 이로써 유기계 절연막이 얻어진다. 여기서, 조성물 3에 사용할 수 있는 유기 용제로는, 예를 들면 n-펜탄, iso-펜탄, n-헥산, iso-헥산, n-헵탄, iso-헵탄, 2,2,4-트리메틸펜탄, n-옥탄, iso-옥탄, 시클로헥산, 메틸시클로헥산 등의 지방족 탄화수소계 용매; 벤젠, 톨루엔, 크실렌, 에틸벤젠, 트리메틸벤젠, 메틸에틸벤젠, n-프로필벤젠, iso-프로필벤젠, 디에틸벤젠, iso-부틸벤젠, 트리에틸벤젠, 디-iso-프로필벤젠, n-아밀나프탈렌 및 트리메틸벤젠 등의 방향족 탄화수소계 용매; 메탄올, 에탄올, n-프로판올, iso-프로판올, n-부탄올, iso-부탄올, sec-부탄올, t-부탄올, n-헵탄올, iso-펜탄올, 2-메틸부탄올, sec-펜탄올, t-펜탄올, 3-메톡시부탄올, n-헥산올, 2-메틸펜탄올, sec-헥산올, 2-에틸부탄올, sec-헵탄올, 3-헵탄올, n-옥탄올, 2-에틸헥산올, sec-옥탄올, n-노닐알코올, 2,6-디메틸-4-헵탄올, n-데칸올, sec-운데실알코올, 트리메틸노닐알코올, sec-테트라데실알코올, sec-헵타데실알코올, 페놀, 시클로헥산올, 메틸시클로헥산올, 3,3,5-트리메틸시클로헥산올, 벤질알코올, 페닐메틸카르비놀, 디아세톤알코올, 크레졸 등의 모노알코올계 용매; 에틸렌글리콜, 1,2-프로필렌글리콜, 1,3-부틸렌글리콜, 2,4-펜탄디올, 2-메틸-2,4-펜탄디올, 2,5-헥산디올, 2,4-헵탄디올, 2-에틸-1,3-헥산디올, 디에틸렌글리콜, 디프로필렌글리콜, 트리에틸렌글리콜, 트리프로필렌글리콜, 글리세린 등의 다가 알코올계 용매; 아세톤, 메틸에틸케톤, 메틸-n-프로필케톤, 메틸-n-부틸케톤, 디에틸케톤, 메틸-iso-부틸케톤, 메틸-n-펜틸케톤, 에틸-n-부틸케톤, 메틸-n-헥실케톤, 디-iso-부틸케톤, 트리메틸노나논, 시클로헥사논, 시클로펜타논, 2-헥사논, 메틸시클로헥사논, 2,4-펜탄디온, 아세토닐아세톤, 디아세톤알코올, 아세토페논, 펜촌 등의 케톤계 용매; 에틸에테르, iso-프로필에테르, n-부틸에테르, n-헥실에테르, 2-에틸헥실에테르, 에틸렌옥시드, 1,2-프로필렌옥시드, 디옥솔란, 4-메틸디옥솔란, 디옥산, 디메틸디옥산, 에틸렌글리콜 모노메틸에테르, 에틸렌글리콜 모노에틸에테르, 에틸렌글리콜 디에틸에테르, 에틸렌글리콜 모노-n-부틸에테르, 에틸렌글리콜 모노-n-헥실에테르, 에틸렌글리콜 모노페닐에테르, 에틸렌글리콜 모노-2-에틸부틸에테르, 에틸렌글리콜 디부틸에테르, 디에틸렌글리콜 모노메틸에테르, 디에틸렌글리콜 모노에틸에테르, 디에틸렌글리콜 디에틸에테르, 디에틸렌글리콜 모노-n-부틸에테르, 디에틸렌글리콜 디-n-부틸에테르, 디에틸렌글리콜 모노-n-헥실에테르, 에톡시트리글리콜, 테트라에틸렌글리콜 디-n-부틸에테르, 프로필렌글리콜 모노메틸에테르, 프로필렌글리콜 모노에틸에테르, 프로필렌글리콜 모노프로필에테르, 프로필렌글리콜 모노부틸에테르, 디프로필렌글리콜 모노메틸에테르, 디프로필렌글리콜 모노에틸에테르, 트리프로필렌글리콜 모노메틸에테르, 테트라히드로푸란, 2-메틸테트라히드로푸란 등의 에테르계 용매; 디에틸카르보네이트, 아세트산메틸, 아세트산에틸, γ-부티로락톤, γ-발레로락톤, 아세트산 n-프로필, 아세트산 iso-프로필, 아세트산 n-부틸, 아세트산 iso-부틸, 아세트산 sec-부틸, 아세트산 n-펜틸, 아세트산 sec-펜틸, 아세트산 3-메톡시부틸, 아세트산 메틸펜틸, 아세트산 2-에틸부틸, 아세트산 2-에틸헥실, 아세트산 벤질, 아세트산 시클로헥실, 아세트산 메틸시클로헥실, 아세트산 n-노닐, 아세토아세트산메틸, 아세토아세트산에틸, 아세트산 에틸렌글리콜 모노메틸에테르, 아세트산 디에틸렌글리콜 모노에틸에테르, 아세트산 디에틸렌글리콜 모노-n-부틸에테르, 아세트산 프로필렌글리콜 모노에틸에테르, 아세트산 프로필렌글리콜 모노프로필에테르, 아세트산 프로필렌글리콜 모노부틸에테르, 아세트산 디프로필렌글리콜 모노메틸에테르, 아세트산 디프로필렌글리콜 모노에틸에테르, 디아세트산 글리콜, 아세트산메톡시트리글리콜, 프로피온산에틸, 프로피온산 n-부틸, 프로피온산 iso-아밀, 옥살산 디에틸, 옥살산 디-n-부틸, 락트산메틸, 락트산에틸, 락트산 n-부틸, 락트산 n-아밀, 말론산 디에틸, 프탈산 디메틸, 프탈산 디에틸 등의 에스테르계 용매; N-메틸포름아미드, N,N-디메틸포름아미드, N,N-디에틸포름아미드, 아세트아미드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸프로피온아미드, N-메틸피롤리돈 등의 질소 함유계 용매; 황화디메틸, 황화디에틸, 티오펜, 테트라히드로티오펜, 디메틸술폭시드, 술포란, 1,3-프로판술톤 등의 황 함유계 용매 등을 들 수 있다. 이들 용제는 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다.
또한, 본 발명의 막 형성용 조성물에는, 콜로이드상 실리카, 유기계 절연막을 형성하기 위해서 사용되는 화합물 5 내지 9 이외의 유기 중합체, 계면활성제, 실란 커플링제, 라디칼 발생제, 중합성 이중 결합을 함유하는 화합물, 중합성 3중 결합 등의 성분을 추가로 첨가할 수도 있다.
3.3. 유기계 절연막의 막 형성 방법
유기계 절연막은, 상기 조성물 3을 기재에 도포하고, 용매를 제거한 후, 도막을 가열에 의해서 경화시킴으로써 형성할 수 있다. 우선, 조성물 3의 기재에의 도포 방법으로는, 스핀 코팅, 디핑, 롤러 블레이드, 스프레이법 등을 들 수 있다. 이때의 막 두께는, 건조 막 두께로서 1회 도포로 두께 1 내지 1000 nm 정도, 2회 도포로는 두께 2 내지 2000 nm 정도의 도막을 형성할 수 있다.
가열하는 방법으로는, 예를 들면 60 내지 600 ℃ 정도의 온도에서 통상적으 로 1 분 내지 240 분 정도 가열하여 도막을 건조시킬 수 있다. 이 경우, 가열 방법으로는 핫 플레이트, 오븐, 퍼니스 등을 사용할 수 있고, 가열 분위기로는 대기하, 질소 분위기하, 아르곤 분위기하, 진공하, 산소 농도가 제어된 감압하 등에서 행할 수 있다. 또한, 전자선이나 자외선을 조사함으로써도 도막을 형성시킬 수 있고, 이 경우는 건조 시간을 단축 가능한 점에서 바람직하다.
이들 적층 절연막을 형성하는 데 있어서, 폴리실록산층, 폴리카르보실란층 및 유기막을 각각 반경화의 상태로 적층한 후, 3층을 일괄적으로 경화시킴으로써 공정 시간을 짧게 할 수도 있다.
4. 절연막
본 발명의 절연막은, 상술한 절연막의 형성 방법에 의해 얻어지는 절연막이다. 즉, 적어도 폴리카르보실란계 절연막, 폴리카르보실란계 절연막 및 유기계 절연막이 적층된 다층 절연막이다. 이 절연막에서는, 소위 Low-k막인 폴리실록산계 절연막과 유기계 절연막 사이에 폴리카르보실란계 절연막이 존재한다. 폴리카르보실란계 절연막은, RIE 등에 의한 에칭 처리 분위기에 노출된 경우에도 에칭 손상을 받는 경우가 적다. 그 때문에, 유기계 절연막의 하층에 있는 폴리실록산계 절연막에 에칭 손상을 주지 않는다. 따라서, 본 발명의 절연막은 폴리실록산계 절연막의 낮은 비유전율을 유지하면서 에칭, 애싱 또는 습식 세정 등의 공정에 대한 내성 등도 우수하다.
또한, 본 발명의 절연막은, 듀얼 다마신 구조를 갖는 배선층을 갖는 반도체 장치에서 비아부를 형성하는 층에는 폴리실록산계 절연막을 이용하고, 트렌치부를 형성하는 층에는 유기계 절연막을 이용하는 경우에 특히 이점을 갖는다. 이 양태에서는, 우선 트렌치부를 형성하기 위해서 유기계 절연막의 에칭이 행해지지만, 이 에칭에 있어서, 하층에 있는 폴리실록산계 절연막 중에 에칭 손상이 생기는 경우가 있다. 그러나, 본 발명에 따르면, 폴리카르보실란계 절연막을 유기계 절연막과 폴리실록산계 절연막 사이에 개재시킴으로써 폴리실록산계 절연막을 보호할 수 있다. 그 때문에, 본 발명의 절연막에 따르면, 보다 신뢰성이 높은 배선층을 갖는 반도체 장치를 제공할 수 있다.
본 발명의 절연막은 LSI, 시스템 LSI, DRAM, SDRAM, RDRAM, D-RDRAM 등의 반도체 소자용 층간 절연막, 반도체 소자의 표면 코팅막 등의 보호막, 다층 배선 기판의 층간 절연막, 액정 표시 소자용 보호막이나 절연 방지막 등의 용도에 유용하다.
5. 실시예
이어서, 본 발명을 실시예를 들어 더욱 구체적으로 설명한다. 또한, 실시예 및 비교예 중의「부」 및 「%」는 특별히 기재하지 않는 한, 각각 중량부 및 중량%를 나타낸다. 단, 이하의 기재는 본 발명의 양태를 개괄적으로 나타내는 것이며, 이러한 기재에 의해 본 발명이 한정되는 것은 아니다.
5.1. 폴리카르보실란 용액의 제조
5.1.1. 제조예 1
시판 폴리카르보실란(상품명 「NIPUSI Type-s」, 닛본 카본 가부시끼가이샤 로부터 입수 가능한 폴리디메틸실란의 카르보실란화 중합체)를 프로필렌글리콜 모노프로필에테르와 시클로헥사논의 혼합 용액(중량비; 프로필렌글리콜 모노프로필에테르:시클로헥사논=50:50)에 고형분 함유량 2 %가 되도록 용해시켜 막 형성용 조성물 (A)를 얻었다.
5.1.2. 제조예 2
폴리알릴디히드로카르보실란(상품명「SP-10」, 스타파이아사로부터 입수 가능한 폴리디메틸실란의 카르보실란화 중합체)를 프로필렌글리콜 모노프로필에테르와 2-헵타논의 혼합 용액(중량비; 프로필렌글리콜 모노프로필에테르:2-헵타논=50:50)에 고형분 함유량 2 %가 되도록 용해시켜 막 형성용 조성물 (B)를 얻었다.
5.2. 절연막의 형성
5.2.1. 실시예 1
우선, 이하의 방법으로 폴리실록산 화합물을 얻었다. 석영제 분리 플라스크에 증류 에탄올 570 g, 이온 교환수 160 g 및 10 % 수산화테트라메틸암모늄 수용액 30 g을 넣어 균일하게 교반하였다. 다음에, 이 용액에 메틸트리메톡시실란 136 g와 테트라에톡시실란 209 g의 혼합물을 첨가하였다. 용액을 55 ℃로 유지한 채로 2 시간 반응을 수행하였다. 이어서, 이 용액에 프로필렌글리콜 모노프로필에테르 300 g을 첨가하고, 그 후 50 ℃의 증발기를 이용하여 용액을 10 %(완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후 아세트산의 10 % 프로필렌글리콜 모노프로필에테르 용액 10 g을 첨가하여 도포액을 얻었다. 이 도포액을 0.2 ㎛ 공경의 테플론(등록 상표)제 필터로 여과를 수행하여 폴리실록산 화합물의 막 형성용 조성 물 (C)를 얻었다.
이 막 형성용 조성물 (C)를 8 인치의 실리콘 웨이퍼 상에 스핀 코팅에 의해서 도포하고, 400 ℃에서 소성하여 Low-k막인 폴리실록산계 절연막(막 두께 400 nm, 유전율 2.3)을 얻었다.
이어서, 이 폴리실록산계 절연막 상에 막 형성용 조성물 (A)를 스핀 코팅으로 도포하고, 80 ℃에서 1 분간, 또한 200 ℃에서 1 분간 건조시켜 보호층인 폴리카르보실란계 절연막(막 두께 10 nm)을 형성하였다.
이어서, 이 폴리카르보실란계 절연막 상에 유기계 절연막을 형성하였다. 이 유기계 절연막의 형성에 있어서는, 우선 이하의 방법에 의해 유기계 절연막을 위한 막 형성용 조성물 (D)를 제조하였다.
온도계, 아르곤 가스 도입관, 교반 장치를 구비한 1,000 ml의 3구 플라스크에 테트라히드로푸란 120 ml, 테트라키스트리페닐포스핀팔라듐 3.46 g, 디클로로비스트리페닐포스핀팔라듐 2.1 g, 요오드화구리(I) 44 g, 피페리딘 20 ml 및 4,4'-비스(2-요오도페녹시)벤조페논 185.72 g을 첨가하였다. 다음에, 4,4'-디에티닐디페닐에테르 65.48 g을 첨가하여 25 ℃에서 20 시간 반응시켰다. 이 반응액을 아세트산 5 리터로 재침전을 2회 반복한 후, 시클로헥사논에 용해시켜 초순수로 2회 세정하였다. 이어서, 메탄올 5 리터로 재침전시키고, 얻어진 침전물을 여과 및 건조시켜 중량 평균 분자량 35,000의 중합체를 얻었다. 이 중합체 20 g을 시클로헥사논 180 g에 용해시켜 막 형성용 조성물 (D)를 얻었다.
또한, 상기 중합체의 중량 평균 분자량(Mw)은 하기 조건에 의한 겔 투과 크 로마토그래피(GPC)법에 의해 측정하였다.
시료: 테트라히드로푸란을 용매로서 사용하여, 중합체 1 g을 100 cc의 테트라히드로푸란에 용해시켜 제조하였다.
표준 폴리스티렌: 미국 프레셔 케미컬사 제조의 표준 폴리스티렌을 사용하였다.
장치: 미국 워터스사 제조의 고온 고속 겔 침투 크로마토그램(모델 150-CALC/GPC)
칼럼: 쇼와 덴꼬(주) 제조의 SHODEX A-80M(길이 50 cm)
측정 온도: 40 ℃
이 막 형성용 조성물 (D)를 폴리카르보실란계 절연막 상에 스핀 코팅법에 의해 도포하였다. 그 후, 400 ℃에서 1 시간의 소성을 수행하여 유기계 절연막을 형성하였다.
이와 같이 하여, 3층의 절연막의 적층체를 포함하는 실시예 1의 절연막을 얻었다.
5.2.2. 실시예 2
실시예 1에서 얻어진 것과 동일한 막 형성용 조성물 (C)를 8 인치의 실리콘 웨이퍼 상에 스핀 코팅에 의해서 도포하고, 80 ℃에서 1 분간, 이어서 200 ℃에서 1 분간 건조시켜 미경화 폴리실록산계 절연막(막 두께 400 nm)을 얻었다.
다음에, 이 미경화 폴리실록산계 절연막 상에 막 형성용 조성물 (A)를 스핀 코팅으로 도포하고, 80 ℃에서 1 분간, 또한 200 ℃에서 1 분간 건조시켜 보호층인 폴리카르보실란계 절연막(막 두께 10 nm)을 형성하였다.
이어서, 막 형성용 조성물 (D)를 폴리카르보실란계 절연막 상에 스핀 코팅법에 의해 도포하였다. 그 후, 400 ℃에서 1 시간의 소성을 수행하여 유기계 절연막을 형성하였다.
이와 같이 하여, 3층의 절연막의 적층체를 포함하는 실시예 2의 절연막을 얻었다.
5.2.3. 실시예 3
실시예 1에서 얻어진 것과 동일한 막 형성용 조성물 (C)를 이용하여, 이 막 형성용 조성물 (C)를 8 인치의 실리콘 웨이퍼 상에 스핀 코팅에 의해서 도포하고, 80 ℃에서 1 분간, 이어서 200 ℃에서 1 분간 건조시켜 미경화 폴리실록산계 절연막(막 두께 400 nm)를 얻었다.
이어서, 이 미경화 폴리실록산계 절연막 상에 막 형성용 조성물 (B)를 스핀 코팅으로 도포하고, 80 ℃에서 1 분간, 또한 200 ℃에서 1 분간 건조시켜 보호층인 폴리카르보실란계 절연막(막 두께 10 nm)을 형성하였다.
이어서, 막 형성용 조성물 (D)를 폴리카르보실란계 절연막 상에 스핀 코팅법에 의해 도포하였다. 그 후, 400 ℃에서 1 시간의 소성을 수행하여 유기계 절연막을 형성하였다.
이와 같이 하여, 3층의 절연막의 적층체를 포함하는 실시예 3의 절연막을 얻었다.
5.2.4. 비교예 1
실시예 1에서 얻어진 막 형성용 조성물 (C)를 8 인치의 실리콘 웨이퍼 상에 스핀 코팅에 의해서 도포하고, 400 ℃에서 소성하여 폴리실록산계 절연막(막 두께400 nm, 유전율 2.3)을 얻었다.
이어서, 막 형성용 조성물 (D)를 폴리실록산계 절연막 상에 스핀 코팅법에 의해 도포하였다. 그 후, 400 ℃에서 1 시간의 소성을 수행하여 유기계 절연막을 형성하였다. 이 비교예 1에서는, 보호층인 폴리카르보실란계 절연막을 형성하지 않고, 2층의 적층체를 포함하는 절연막을 얻었다.
5.3. 절연막의 평가
5.3.1. 비유전율의 측정
얻어진 절연막에 증착법에 의해 알루미늄 전극 패턴을 형성시켜 비유전율 측정용 샘플을 제조하였다. 100 kHz의 주파수에서 요코가와ㆍ휴렛 팩커드(주) 제조의 HP16451B 전극 및 HP4284A 프레시젼 LCR 미터를 이용하여 CV법에 의해 각 샘플에 대한 비유전율을 측정하였다. 측정 결과를 표 1에 나타낸다.
5.3.2. 막 두께의 평가
N&K 테크놀로지사 제조, n&k 애널라이저 1500의 다층 해석 모드를 이용하여, 적층체를 포함하는 절연막의 각 층의 막 두께를 산출하였다. 이와 같이 하여 산출한 각 층의 막 두께는 5.2.3.의 비유전율을 구할 때에 이용하였다.
5.3.3. 폴리실록산계 절연막의 비유전율의 추출
별도로, 실리콘 웨이퍼 상에 막을 형성한 유기계 절연막의 비유전율을 측정하고, 적층 후에도 유기계 절연막은 이 비유전율을 갖는 것으로 하였다. 이 비유 전율의 값을 이용하여, 다층 해석에 의해서 얻어진 각 층의 막 두께 및 적층체의 비유전율의 측정 결과로부터, 직렬 캐패시터 모델을 이용하여 폴리실록산계 절연막의 비유전율을 산출하였다. 측정 결과를 표 1에 나타낸다.
5.3.4. 막의 약물 내성(공정 내성)
각 실시예 1 내지 3 및 비교예 1에서 얻어진 웨이퍼 적층체를 2 mm×10 mm의 크기로 파단하여 샘플을 형성하였다. 이 샘플을 실온에서 0.2 %의 묽은 불산 수용액 중에 1 분간 침지하였다. 샘플의 파단면을 SEM에서 관찰하고, 폴리실록산계 절연막이 묽은 불산에 의해 에칭되었는지 여부를 관찰하였다. 측정 결과를 표 1에 나타낸다.
5.3.5. RIE 내성 평가
각 실시예 1 내지 3 및 비교예 1에 의해 얻어진 절연막에 대하여, 400 ℃, 1 시간, 질소 분위기하에서 소성을 수행한 후, 각 적층막을 도꾜 일렉트론사 제조 플라즈마 에칭 장치를 이용하여, 암모니아 또는 산소를 이용하는 유기 Low-k막 에칭 조건에 노출시키고, 노출 전후의 실록산 Low-k막의 유전율 변화로부터 RIE 내성을 평가하였다. 또한, 노출 전후 폴리실록산계 절연막의 비유전율의 측정 결과를 표 1에 나타낸다.
5.3.6. 파괴 인성 측정
4점 굽힘법(4-point bending method)을 이용하여, 실시예 1 내지 3 및 비교예 1에 의해 얻어진 절연막의 폴리실록산계 절연막 및 유기 절연막 계면의 접착 강도를 측정하였다. 측정 결과를 표 2에 나타낸다.
실시예 1 내지 3의 절연막에서, 폴리카르보실란계 절연막은 폴리실록산계 절연막 상에 형성되어 있고, 이 폴리카르보실란계 절연막은 폴리실록산계 절연막의 보호층으로서 기능한다. 이 때문에, 표 1에 나타낸 바와 같이, 실시예 1 내지 3의 절연막에서, 폴리카르보실란계 절연막을 폴리실록산계 절연막 상에 형성한 경우에는, 비유전율의 상승 및 불산에 의한 에칭이 확인되지 않았다. 이에 의해, 실시예 1 내지 3의 절연막에 따르면, 폴리실록산계 절연막의 위쪽에 형성된 유기계 절연막을 에칭할 때 생기는 손상(에칭에서 사용되는 플라즈마에 의한 손상)을 억제할 수 있는 것이 확인되었다.
이에 반해, 비교예 1의 절연막에서는, 폴리카르보실란계 절연막이 형성되어 있지 않기 때문에, 표 1에 나타낸 바와 같이 에칭에 의한 손상이 생길 뿐만 아니라 비유전율이 상승하는 것도 확인되었다.
또한, 표 2에 나타낸 바와 같이, 실시예 1 내지 3의 절연막은 비교예 1의 절연막에 비해, 파괴 인성이 양호하고, 또한 밀착 강도가 향상된 것이 확인되었다.
Claims (4)
- 기재 상에 폴리실록산계 절연막을 형성하는 공정,상기 폴리실록산계 절연막 상에 폴리카르보실란계 절연막을 형성하는 공정, 및상기 폴리카르보실란계 절연막 상에 유기계 절연막을 형성하는 공정을 포함하는 절연막의 형성 방법으로서,상기 폴리실록산계 절연막은, 하기 화학식 1 내지 3으로 표시되는 화합물의 군에서 선택된 1종 이상의 실란 화합물을 가수분해 축합시킴으로써 형성되고,상기 폴리카르보실란계 절연막은, 하기 화학식 4로 표시되는 폴리카르보실란 화합물을 용매에 용해시킴으로써 얻어진 용액을 도포한 후, 도막을 가열함으로써 형성되는 것인 절연막의 형성 방법.<화학식 1>RaSi(OR1)4-a<화학식 2>Si(OR2)4<화학식 3>R3 b(R4O)3-bSi-(R7)d-Si(OR5)3-cR6 c<화학식 4>식 중, R은 수소 원자, 불소 원자 또는 유기기를 나타내고, R1은 유기기를 나타내고, a는 1 또는 2의 정수를 나타내고;R2는 유기기를 나타내고;R3 내지 R6은 동일하거나 상이하며, 각각 유기기를 나타내고, b 및 c는 동일하거나 상이하며, 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)m-으로 표시되는 기(여기서, m은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타내고;R8 내지 R11은 동일하거나 상이하며, 수소 원자, 할로겐 원자, 히드록실기, 알콕실기, 술폰기, 메탄술폰기, 트리플루오로메탄술폰기 또는 유기기를 나타내고, R12 내지 R14는 동일하거나 상이하며, 치환 또는 비치환의 알킬렌기, 알케닐기, 알키닐기 또는 아릴렌기를 나타내고, x, y 및 z는 0 내지 10,000의 정수이며, 10<x+y+z<20,000의 조건을 만족시킨다.
- 제1항에 있어서, 상기 유기계 절연막이, 폴리아릴렌, 폴리아릴렌에테르, 폴 리옥사졸린 및 폴리벤조시클로부텐 골격을 갖는 중합체 중 1종 이상을 용제에 용해 또는 분산시킴으로써 얻어진 용액을 도포한 후, 도막을 가열함으로써 형성되는 것인 절연막의 형성 방법.
- 기재 상에 형성된폴리실록산계 절연막,상기 폴리실록산계 절연막 상에 형성된 폴리카르보실란계 절연막, 및상기 폴리카르보실란계 절연막 상에 형성된 유기계 절연막을 포함하는 절연막으로서,상기 폴리실록산계 절연막은, 하기 화학식 1 내지 3으로 표시되는 화합물의 군에서 선택된 1종 이상의 실란 화합물을 가수분해 축합시킴으로써 형성되고,상기 폴리카르보실란계 절연막은, 하기 화학식 4로 표시되는 폴리카르보실란 화합물을 용매에 용해시킴으로써 얻어진 용액을 도포한 후, 도막을 가열함으로써 형성되는 것인 절연막.<화학식 1>RaSi(OR1)4-a<화학식 2>Si(OR2)4<화학식 3>R3 b(R4O)3-bSi-(R7)d-Si(OR5)3-cR6 c<화학식 4>식 중, R은 수소 원자, 불소 원자 또는 유기기를 나타내고, R1은 유기기를 나타내고, a는 1 또는 2의 정수를 나타내고;R2는 유기기를 나타내고;R3 내지 R6은 동일하거나 상이하며, 각각 유기기를 나타내고, b 및 c는 동일하거나 상이하며, 0 내지 2의 수를 나타내고, R7은 산소 원자, 페닐렌기 또는 -(CH2)m-으로 표시되는 기(여기서, m은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타내고;R8 내지 R11은 동일하거나 상이하며, 수소 원자, 할로겐 원자, 히드록실기, 알콕실기, 술폰기, 메탄술폰기, 트리플루오로메탄술폰기 또는 유기기를 나타내고, R12 내지 R14는 동일하거나 상이하며, 치환 또는 비치환의 알킬렌기, 알케닐기, 알키닐기 또는 아릴렌기를 나타내고, x, y 및 z는 0 내지 10,000의 정수이며, 10<x+y+z<20,000의 조건을 만족시킨다.
- 제3항에 있어서, 상기 유기계 절연막이, 폴리아릴렌, 폴리아릴렌에테르, 폴리옥사졸린 및 폴리벤조시클로부텐 중 1종 이상을 용제에 용해 또는 분산시킴으로써 얻어진 용액을 도포한 후, 도막을 가열함으로써 형성된 것인 절연막.
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