KR101129875B1 - 중합체의 제조 방법, 중합체, 절연막 형성용 조성물,절연막의 제조 방법 및 절연막 - Google Patents
중합체의 제조 방법, 중합체, 절연막 형성용 조성물,절연막의 제조 방법 및 절연막 Download PDFInfo
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- KR101129875B1 KR101129875B1 KR1020067016327A KR20067016327A KR101129875B1 KR 101129875 B1 KR101129875 B1 KR 101129875B1 KR 1020067016327 A KR1020067016327 A KR 1020067016327A KR 20067016327 A KR20067016327 A KR 20067016327A KR 101129875 B1 KR101129875 B1 KR 101129875B1
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- polymer
- propoxysilane
- insulating film
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- 229920000642 polymer Polymers 0.000 title claims abstract description 80
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 229910000077 silane Inorganic materials 0.000 claims abstract description 32
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229920003257 polycarbosilane Polymers 0.000 claims abstract description 25
- 125000005843 halogen group Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
- -1 silane compound Chemical class 0.000 claims description 73
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 27
- 238000000576 coating method Methods 0.000 claims description 25
- 239000011248 coating agent Substances 0.000 claims description 24
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 abstract description 15
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- 239000004065 semiconductor Substances 0.000 abstract description 7
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 46
- 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 42
- 238000006243 chemical reaction Methods 0.000 description 37
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- 239000010936 titanium Substances 0.000 description 21
- 229910052719 titanium Inorganic materials 0.000 description 21
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 20
- 229910052726 zirconium Inorganic materials 0.000 description 20
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- 239000007983 Tris buffer Substances 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000013522 chelant Substances 0.000 description 8
- 239000012295 chemical reaction liquid Substances 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- 229940126214 compound 3 Drugs 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GSCOPSVHEGTJRH-UHFFFAOYSA-J [Ti+4].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O Chemical compound [Ti+4].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O GSCOPSVHEGTJRH-UHFFFAOYSA-J 0.000 description 6
- 239000003638 chemical reducing agent Substances 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
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 5
- AMUZLNGQQFNPTQ-UHFFFAOYSA-J 3-oxohexanoate zirconium(4+) Chemical compound [Zr+4].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O AMUZLNGQQFNPTQ-UHFFFAOYSA-J 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 5
- JCHGDLSNQMRKGZ-UHFFFAOYSA-N [SiH4].[I] Chemical compound [SiH4].[I] JCHGDLSNQMRKGZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000005215 alkyl ethers Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
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- 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
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 4
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- FYTPGBJPTDQJCG-UHFFFAOYSA-N Trichloro(chloromethyl)silane Chemical compound ClC[Si](Cl)(Cl)Cl FYTPGBJPTDQJCG-UHFFFAOYSA-N 0.000 description 4
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- 239000003513 alkali Substances 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 4
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- 239000011737 fluorine Substances 0.000 description 4
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- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
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- 239000005055 methyl trichlorosilane Substances 0.000 description 4
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- 239000011259 mixed solution Substances 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
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- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 4
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- 238000013001 point bending Methods 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- PDWJQUIPTZSMQV-UHFFFAOYSA-N propyl 3-oxohexaneperoxoate;zirconium Chemical compound [Zr].CCCOOC(=O)CC(=O)CCC.CCCOOC(=O)CC(=O)CCC PDWJQUIPTZSMQV-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- NVQCTSGVFRPZCZ-UHFFFAOYSA-N tert-butyl 3-oxohexaneperoxoate;zirconium Chemical compound [Zr].CCCC(=O)CC(=O)OOC(C)(C)C.CCCC(=O)CC(=O)OOC(C)(C)C NVQCTSGVFRPZCZ-UHFFFAOYSA-N 0.000 description 1
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- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VMJIXANYDQPYPU-UHFFFAOYSA-N tert-butyl-(chloromethyl)-di(propan-2-yloxy)silane Chemical compound CC(C)O[Si](CCl)(C(C)(C)C)OC(C)C VMJIXANYDQPYPU-UHFFFAOYSA-N 0.000 description 1
- AZWJKWJFAHCSAS-UHFFFAOYSA-N tert-butyl-(chloromethyl)-diethoxysilane Chemical compound CCO[Si](CCl)(C(C)(C)C)OCC AZWJKWJFAHCSAS-UHFFFAOYSA-N 0.000 description 1
- XMDNCXJUXMWGDW-UHFFFAOYSA-N tert-butyl-(chloromethyl)-dimethoxysilane Chemical compound CO[Si](CCl)(OC)C(C)(C)C XMDNCXJUXMWGDW-UHFFFAOYSA-N 0.000 description 1
- KINVROKQEPWGJJ-UHFFFAOYSA-N tert-butyl-(chloromethyl)-dipropoxysilane Chemical compound CCCO[Si](CCl)(C(C)(C)C)OCCC KINVROKQEPWGJJ-UHFFFAOYSA-N 0.000 description 1
- HQGVGCFRRIKVKV-UHFFFAOYSA-N tert-butyl-dichloro-(chloromethyl)silane Chemical compound CC(C)(C)[Si](Cl)(Cl)CCl HQGVGCFRRIKVKV-UHFFFAOYSA-N 0.000 description 1
- ULXGRUZMLVGCGL-UHFFFAOYSA-N tert-butyl-tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C(C)(C)C ULXGRUZMLVGCGL-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- FTWJZZHBSKNAPN-UHFFFAOYSA-N tri(butan-2-yloxy)-[2-[di(butan-2-yloxy)methylsilyl]ethyl]silane Chemical compound CCC(C)OC(OC(C)CC)[SiH2]CC[Si](OC(C)CC)(OC(C)CC)OC(C)CC FTWJZZHBSKNAPN-UHFFFAOYSA-N 0.000 description 1
- KLPWIDSFARMZQW-UHFFFAOYSA-N tri(butan-2-yloxy)-[2-tri(butan-2-yloxy)silylethyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)CC[Si](OC(C)CC)(OC(C)CC)OC(C)CC KLPWIDSFARMZQW-UHFFFAOYSA-N 0.000 description 1
- IVRXTRZVBJSOLZ-UHFFFAOYSA-N tri(butan-2-yloxy)-[2-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC=C1[Si](OC(C)CC)(OC(C)CC)OC(C)CC IVRXTRZVBJSOLZ-UHFFFAOYSA-N 0.000 description 1
- SGZJOYFOVHWDFY-UHFFFAOYSA-N tri(butan-2-yloxy)-[3-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC([Si](OC(C)CC)(OC(C)CC)OC(C)CC)=C1 SGZJOYFOVHWDFY-UHFFFAOYSA-N 0.000 description 1
- OHGMZEITXQWDLR-UHFFFAOYSA-N tri(butan-2-yloxy)-[4-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=C([Si](OC(C)CC)(OC(C)CC)OC(C)CC)C=C1 OHGMZEITXQWDLR-UHFFFAOYSA-N 0.000 description 1
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- IKCSBNRFPJTRMT-UHFFFAOYSA-N tri(butan-2-yloxy)-[tri(butan-2-yloxy)silylmethyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C[Si](OC(C)CC)(OC(C)CC)OC(C)CC IKCSBNRFPJTRMT-UHFFFAOYSA-N 0.000 description 1
- JGABXROLARSPEN-UHFFFAOYSA-N tri(propan-2-yloxy)silane Chemical compound CC(C)O[SiH](OC(C)C)OC(C)C JGABXROLARSPEN-UHFFFAOYSA-N 0.000 description 1
- DGTSXRWJKSHSCG-UHFFFAOYSA-N tribromo(1-tribromosilylethyl)silane Chemical compound Br[Si](Br)(Br)C(C)[Si](Br)(Br)Br DGTSXRWJKSHSCG-UHFFFAOYSA-N 0.000 description 1
- ASWZNPOTXAXUPB-UHFFFAOYSA-N tribromo(tribromosilyl)silane Chemical compound Br[Si](Br)(Br)[Si](Br)(Br)Br ASWZNPOTXAXUPB-UHFFFAOYSA-N 0.000 description 1
- NMWWUBJEHVDRJB-UHFFFAOYSA-N tribromo(tribromosilylmethyl)silane Chemical compound Br[Si](Br)(Br)C[Si](Br)(Br)Br NMWWUBJEHVDRJB-UHFFFAOYSA-N 0.000 description 1
- PWVUSFVRYWVBDM-UHFFFAOYSA-N tribromo(tribromosilyloxy)silane Chemical compound Br[Si](Br)(Br)O[Si](Br)(Br)Br PWVUSFVRYWVBDM-UHFFFAOYSA-N 0.000 description 1
- HQVXCNNUHHOIMY-UHFFFAOYSA-N tribromomethylcyclohexane Chemical compound BrC(Br)(Br)C1CCCCC1 HQVXCNNUHHOIMY-UHFFFAOYSA-N 0.000 description 1
- CQLAZINSWMHWAQ-UHFFFAOYSA-N tributoxy(dibutoxymethylsilylmethyl)silane Chemical compound CCCCOC(OCCCC)[SiH2]C[Si](OCCCC)(OCCCC)OCCCC CQLAZINSWMHWAQ-UHFFFAOYSA-N 0.000 description 1
- JXXQPVMVSMWLGZ-UHFFFAOYSA-N tributoxy(tributoxysilylmethyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C[Si](OCCCC)(OCCCC)OCCCC JXXQPVMVSMWLGZ-UHFFFAOYSA-N 0.000 description 1
- ZYXLOEAJFSQDQG-UHFFFAOYSA-N tributoxy-(2-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1[Si](OCCCC)(OCCCC)OCCCC ZYXLOEAJFSQDQG-UHFFFAOYSA-N 0.000 description 1
- UYZUVKDKSJFNIN-UHFFFAOYSA-N tributoxy-(3-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC([Si](OCCCC)(OCCCC)OCCCC)=C1 UYZUVKDKSJFNIN-UHFFFAOYSA-N 0.000 description 1
- YBNXDKRALACDIA-UHFFFAOYSA-N tributoxy-(4-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=C([Si](OCCCC)(OCCCC)OCCCC)C=C1 YBNXDKRALACDIA-UHFFFAOYSA-N 0.000 description 1
- RPWIVYRJUHMXOQ-UHFFFAOYSA-N trichloro(1-chlorobutyl)silane Chemical compound CCCC(Cl)[Si](Cl)(Cl)Cl RPWIVYRJUHMXOQ-UHFFFAOYSA-N 0.000 description 1
- KGTMHSVVFJZNOD-UHFFFAOYSA-N trichloro(1-chloroprop-2-enyl)silane Chemical compound C=CC(Cl)[Si](Cl)(Cl)Cl KGTMHSVVFJZNOD-UHFFFAOYSA-N 0.000 description 1
- QPYFKHDLAURNJO-UHFFFAOYSA-N trichloro(2-chlorobutan-2-yl)silane Chemical compound CCC(C)(Cl)[Si](Cl)(Cl)Cl QPYFKHDLAURNJO-UHFFFAOYSA-N 0.000 description 1
- PPQQGGUAEQVKHK-UHFFFAOYSA-N trichloro(2-chloropropan-2-yl)silane Chemical compound CC(C)(Cl)[Si](Cl)(Cl)Cl PPQQGGUAEQVKHK-UHFFFAOYSA-N 0.000 description 1
- WDVUXWDZTPZIIE-UHFFFAOYSA-N trichloro(2-trichlorosilylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC[Si](Cl)(Cl)Cl WDVUXWDZTPZIIE-UHFFFAOYSA-N 0.000 description 1
- QDPYNKGKKGQJBF-UHFFFAOYSA-N trichloro(3-chloropentan-3-yl)silane Chemical compound CCC(Cl)(CC)[Si](Cl)(Cl)Cl QDPYNKGKKGQJBF-UHFFFAOYSA-N 0.000 description 1
- LQUJCRPJNSUWKY-UHFFFAOYSA-N trichloro(dichloromethyl)silane Chemical compound ClC(Cl)[Si](Cl)(Cl)Cl LQUJCRPJNSUWKY-UHFFFAOYSA-N 0.000 description 1
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 description 1
- ABDDAHLAEXNYRC-UHFFFAOYSA-N trichloro(trichlorosilylmethyl)silane Chemical compound Cl[Si](Cl)(Cl)C[Si](Cl)(Cl)Cl ABDDAHLAEXNYRC-UHFFFAOYSA-N 0.000 description 1
- QHAHOIWVGZZELU-UHFFFAOYSA-N trichloro(trichlorosilyloxy)silane Chemical compound Cl[Si](Cl)(Cl)O[Si](Cl)(Cl)Cl QHAHOIWVGZZELU-UHFFFAOYSA-N 0.000 description 1
- ANUMBTODEQDFNN-UHFFFAOYSA-N trichloromethylcyclohexane Chemical compound ClC(Cl)(Cl)C1CCCCC1 ANUMBTODEQDFNN-UHFFFAOYSA-N 0.000 description 1
- YYJNCOSWWOMZHX-UHFFFAOYSA-N triethoxy-(4-triethoxysilylphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C([Si](OCC)(OCC)OCC)C=C1 YYJNCOSWWOMZHX-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- ARIHFGQDMNMGQJ-UHFFFAOYSA-N triiodo(methyl)silane Chemical compound C[Si](I)(I)I ARIHFGQDMNMGQJ-UHFFFAOYSA-N 0.000 description 1
- CIEKVFFSPFYSHN-UHFFFAOYSA-N triiodo(triiodosilyl)silane Chemical compound I[Si](I)(I)[Si](I)(I)I CIEKVFFSPFYSHN-UHFFFAOYSA-N 0.000 description 1
- DXJQTNKOOPWSPO-UHFFFAOYSA-N triiodomethylbenzene Chemical compound IC(I)(I)C1=CC=CC=C1 DXJQTNKOOPWSPO-UHFFFAOYSA-N 0.000 description 1
- MHKRJMVIDUMJGV-UHFFFAOYSA-N triiodomethylcyclohexane Chemical compound IC(I)(I)C1CCCCC1 MHKRJMVIDUMJGV-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-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
- YRUALOZSEADDBR-UHFFFAOYSA-N triphenyl triphenoxysilyl silicate Chemical compound C=1C=CC=CC=1O[Si](O[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 YRUALOZSEADDBR-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- ORBIWUVSNQKBNY-UHFFFAOYSA-N tris(3-bicyclo[2.2.1]heptanyl)-bromosilane Chemical compound C1C(C2)CCC2C1[Si](Br)(C1C2CCC(C2)C1)C1C(C2)CCC2C1 ORBIWUVSNQKBNY-UHFFFAOYSA-N 0.000 description 1
- BNCOGDMUGQWFQE-UHFFFAOYSA-N tris(ethenyl)silicon Chemical compound C=C[Si](C=C)C=C BNCOGDMUGQWFQE-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
- 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
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
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Abstract
예를 들면, 반도체 소자 등에서의 층간 절연막으로서 바람직하게 사용할 수 있으며, 비유전율이 낮고, 기계적 강도나 밀착성이 우수하며, 균일한 막질을 갖는 막을 형성할 수 있는 중합체의 제조 방법 및 중합체, 절연막 형성용 조성물, 절연막의 제조 방법 및 절연막을 제공한다. 본 발명의 중합체의 제조 방법은, (A) 폴리카르보실란의 존재하에 (B) 가수분해성기 함유 실란 단량체를 가수분해 축합하는 것을 포함하고, 상기 (A) 폴리카르보실란은, (a) 하기 화학식 1로 표시되는 화합물과, (b) 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물의 군으로부터 선택된 1종 이상을 유기 용매 중에서 알칼리 금속 및 알칼리 토금속 중 하나 이상의 존재하에 반응시켜 얻어지는 중합체 (I)이다.
<화학식 1>
R1 kCX4 -k
<화학식 2>
R2 kSiY4 -k
<화학식 3>
R3 mY3 - mSiCR4 nX3 -n
식 중, R1 내지 R4는 동일하거나 상이하고, 각각 1가의 유기기 또는 수소 원자를 나타내며, X는 할로겐 원자를 나타내고, Y는 할로겐 원자 또는 알콕시기를 나타내며, k는 0 내지 3의 정수를 나타내고, m 및 n은 동일하거나 상이하며, 0 내지 2의 정수를 나타낸다.
중합체, 절연막, 비유전율, 기계적 강도, 밀착성, 폴리카르보실란, 실란 단량체
Description
본 발명은 중합체의 제조 방법, 중합체, 절연막 형성용 조성물, 절연막의 제조 방법, 및 절연막에 관한 것이다.
종래, 반도체 소자 등에서의 층간 절연막으로서, CVD(Chemical Vapor Deposition)법 등의 진공 공정으로 형성된 실리카(SiO2)막이 다용되고 있다. 그리고, 최근에는 보다 균일한 층간 절연막을 형성하기 위한 목적으로, SOG(Spin on Glass)막이라 불리는 테트라알콕실란의 가수분해 생성물을 주성분으로 하는 도포형의 절연막도 사용되고 있다. 또한, 반도체 소자 등의 고집적화에 따라, 유기 SOG라 불리는 폴리오르가노실록산을 주성분으로 하는 저 비유전율의 층간 절연막이 개발되어 있다.
특히 반도체 소자 등의 보다 고도의 고집적화나 다층화에 따라, 보다 우수한 도체간의 전기 절연성이 요구되고 있고, 따라서 보다 저 비유전율이며 균열 내성, 기계적 강도 및 밀착성이 우수한 층간 절연막 재료가 요구되고 있다.
저 비유전율의 재료로는, 암모니아의 존재하에 알콕시실란을 축합하여 얻어지는 미립자와 알콕시실란의 염기성 부분 가수분해물과의 혼합물을 포함하는 조성물(일본 특허 공개 (평)5-263045호 공보, 일본 특허 공개 (평)5-315319호 공보)이나, 폴리알콕시실란의 염기성 가수분해물을 암모니아의 존재하에서 축합함으로써 얻어진 도포액(일본 특허 공개 (평)11-340219호 공보, 일본 특허 공개 (평)11-340220호 공보)이 제안되어 있다. 그러나, 이들 방법에서 얻어지는 재료는 반응 생성물의 성질이 불안정하고, 도막의 비유전율, 균열 내성, 기계적 강도, 밀착성 등의 변동도 크기 때문에, 공업적 생산에는 부적합하였다. 또한, 폴리카르보실란 용액과 폴리실록산 용액을 혼합함으로써 도포액을 제조하고, 저유전율 절연막을 형성하는 방법(일본 특허 공개 제2001-127152호 공보)이 제안되어 있지만, 이 방법에서는 카르보실란과 실록산의 도메인이 불균일한 상태에서 도막 중에 각각 분산된다는 문제가 있었다.
또한, 유기 금속 실란 화합물로부터 카본 브릿지 함유 실란 올리고머를 제조한 후, 가수분해 축합되어 얻어지는 유기 실리케이트 중합체를 사용하는 방법(WO 2002-098955)도 제안되어 있지만, 이 방법에서 얻어지는 재료는 반응 생성물의 안정성이 떨어지고 장기 보관이 어려운 재료일 뿐만 아니라, 기판에 대한 밀착성이 떨어진다는 문제점이 있었다.
본 발명의 목적은, 예를 들면 반도체 소자 등에서의 층간 절연막으로서 바람직하게 사용할 수 있으며, 비유전율이 낮고, 기계적 강도나 밀착성이 우수하며, 균일한 막질을 갖는 막을 형성할 수 있는 중합체의 제조 방법 및 중합체를 제공하는 것에 있다.
본 발명의 다른 목적은, 상기 본 발명의 중합체를 사용한 절연막 형성용 조성물, 절연막의 제조 방법 및 절연막을 제공하는 것에 있다.
본 발명에 따른 중합체의 제조 방법은,
(A) 폴리카르보실란의 존재하에 (B) 가수분해성기 함유 실란 단량체를 가수분해 축합하는 것을 포함하고,
상기 (A) 폴리카르보실란은, (a) 하기 화학식 1로 표시되는 화합물과, (b) 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물의 군으로부터 선택된 1종 이상을 유기 용매 중에서 알칼리 금속 및 알칼리 토금속 중 하나 이상의 존재하에 반응시켜 얻어지는 중합체 (I)이다.
식 중, R1 내지 R4는 동일하거나 상이하고, 각각 1가의 유기기 또는 수소 원자를 나타내며, X는 할로겐 원자를 나타내고, Y는 할로겐 원자 또는 알콕시기를 나타내며, k는 0 내지 3의 정수를 나타내고, m 및 n은 동일하거나 상이하며, 0 내지 2의 정수를 나타낸다.
여기서, 상술한 본 발명에 따른 중합체의 제조 방법에서, 상기 (B) 가수분해성기 함유 실란 단량체는 하기 화학식 4로 표시되는 화합물 및 하기 화학식 5로 표시되는 화합물의 군으로부터 선택된 1종 이상의 실란 화합물일 수 있다.
식 중, R5는 수소 원자, 불소 원자 또는 1가의 유기기를 나타내고, X는 할로겐 원자 또는 알콕시기를 나타내며, a는 0 내지 3의 정수를 나타낸다.
식 중, R6, R7은 동일하거나 상이하고, 각각 1가의 유기기를 나타내며, b 및 c는 동일하거나 상이하고, 0 내지 2의 정수를 나타내며, R8은 산소 원자, 페닐렌기 또는 -(CH2)e-로 표시되는 기(여기서, e는 1 내지 6의 정수임)를 나타내고, Y 및 Z는 동일하거나 상이하며, 할로겐 원자 또는 알콕시기를 나타내고, d는 0 또는 1을 나타낸다.
본 발명에 따른 중합체는 상술한 본 발명에 따른 중합체의 제조 방법에 의해서 얻어진다.
본 발명에 따른 절연막 형성용 조성물은 상술한 본 발명에 따른 중합체 및 유기 용제를 함유한다.
본 발명에 따른 절연막의 제조 방법은, 상술한 본 발명에 따른 절연막 형성용 조성물을 기판에 도포하고, 30 내지 450 ℃로 가열하는 것을 포함할 수 있다.
본 발명에 따른 실리카계의 절연막은 상술한 본 발명에 따른 절연막의 제조 방법에 의해 얻어진다.
본 발명의 중합체의 제조 방법에 따르면, (A) 폴리카르보실란의 존재하에 (B) 가수분해성기 함유 실란 단량체를 반응시킴으로써, (B) 가수분해성기 함유 실란 단량체에서 유래하는 폴리실록산과 (A) 폴리카르보실란이 반응한 중합체를 얻을 수 있다. 예를 들면, 가수분해성기를 갖는 (A) 폴리카르보실란의 존재하에 (B) 가수분해성기 함유 실란 단량체를 가수분해 축합함으로써, 일부가 공축합된 중합체를 얻을 수 있다. 이러한 특정한 중합체를 함유하는 막 형성용 조성물을 사용함으로써, 비유전율이 낮고, 기계적 강도나 밀착성이 우수하며 막 중 상분리가 없는 절연막을 얻을 수 있다.
<발명을 실시하기 위한 최선의 형태>
이하, 본 발명을 더욱 상세히 설명한다.
1. 중합체
본 발명의 중합체는, (A) 폴리카르보실란의 존재하에 (B) 가수분해성기 함유 실란 단량체를 가수분해 축합함으로써 얻어지고, (A) 폴리카르보실란은, (a) 하기 화학식 1로 표시되는 화합물과, (b) 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물의 군으로부터 선택된 1종 이상을 유기 용매 중에서 알칼리 금속 및 알칼리 토금속 중 하나 이상의 존재하에서 반응시켜 얻어지는 중합체 (I)이다.
<화학식 1>
R1 kCX4 -k
<화학식 2>
R2 kSiY4 -k
<화학식 3>
R3 mY3 - mSiCR4 nX3 -n
식 중, R1 내지 R4는 동일하거나 상이하고, 각각 1가의 유기기 또는 수소 원자를 나타내며, X는 할로겐 원자를 나타내고, Y는 할로겐 원자 또는 알콕시기를 나타내며, k는 0 내지 3의 정수를 나타내고, m 및 n은 동일하거나 상이하며, 0 내지 2의 정수를 나타낸다.
1.1. (A) 폴리카르보실란
(A) 폴리카르보실란은 중합체 (I)일 수 있다. 중합체 (I)는, (a) 하기 화학식 1로 표시되는 화합물과, (b) 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물의 군으로부터 선택되는 1종 이상을 유기 용매 중에서 알칼리 금속 및 알칼리 토금속 중 하나 이상의 존재하에서 반응시켜 얻어진다.
상기 화학식 1 내지 3에서, R1 내지 R4는 동일하거나 상이하고, 수소 원자 또는 1가의 유기기이다. 1가의 유기기의 구체예로는, 알킬기, 알케닐기, 알키닐기 등의 탄소수가 1 내지 10인 직쇄상 또는 분지쇄상 지방족기; 시클로알킬기, 시클로알케닐기, 비시클로알킬기 등의 탄소수가 3 내지 20인 지환식기; 탄소수가 6 내지 20인 아릴기; 및 탄소수가 6 내지 20인 아랄킬기를 들 수 있다.
알킬기로는, 예를 들면 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, 이소부틸기, t-부틸기 n-펜틸기, 이소펜틸기, 네오펜틸기 등을 들 수 있다.
알케닐기로는, 예를 들면 비닐기, 프로페닐기, 3-부테닐기, 3-펜테닐기, 3-헥세닐기를 들 수 있다.
알키닐기로는, 예를 들면 프로파길기, 3-메틸프로파길기, 3-에틸프로파길기 등을 들 수 있다.
시클로알킬기로는, 예를 들면 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 노르보르닐기 등을 들 수 있다.
아릴기로는, 예를 들면 페닐기, 톨릴기, 크실릴기, α-나프틸기, β-나프틸기, α-티오펜기, β-티오펜기 등을 들 수 있다.
아랄킬기로는, 예를 들면 벤질기, 페네틸기, 페닐프로필기, 페닐부틸기 등을 들 수 있다.
X, Y로 표시되는 할로겐 원자로는, 불소 원자, 염소 원자, 브롬 원자, 요오드 원자를 들 수 있다. 또한, Y로 표시되는 알콕시기(-OR)의 R로는, 상기 R1 내지 R4 중, 알킬기 및 아릴기와 마찬가지의 것을 들 수 있다.
(A) 성분의 폴리카르보실란의 폴리스티렌 환산 중량 평균 분자량은 400 내지 50,000인 것이 바람직하고, 500 내지 10,000인 것이 보다 바람직하며, 500 내지 3,000인 것이 더욱 바람직하다. (B) 성분의 폴리스티렌 환산 중량 평균 분자량이 50,000을 초과하면, (A) 성분과 층 분리를 일으켜 균일한 막을 형성하지 않는 경우가 있다.
1.1.1. 화합물 1
화학식 1로 표시되는 화합물(이하, "화합물 1"이라 함)로는, 테트라클로로카본, 테트라브로모카본, 테트라요오드카본, 클로로포름, 브로모포름, 요오드포름, 메틸트리클로로카본, 에틸트리클로로카본, n-프로필트리클로로카본, 이소프로필트리클로로카본, n-부틸트리클로로카본, t-부틸트리클로로카본, 시클로헥실트리클로로카본, 페네틸트리클로로카본, 2-노르보르닐트리클로로카본, 비닐트리클로로카본, 페닐트리클로로카본, 메틸트리브로모카본, 에틸트리브로모카본, n-프로필트리브로모카본, 이소프로필트리브로모카본, n-부틸트리브로모카본, t-부틸트리브로모카본, 시클로헥실트리브로모카본, 페네틸트리브로모카본, 2-노르보르닐트리브로모카본, 비닐트리브로모카본, 페닐트리브로모카본, 메틸트리요오드카본, 에틸트리요오드카본, n-프로필트리요오드카본, 이소프로필트리요오드카본, n-부틸트리요오드카본, t-부틸트리요오드카본, 시클로헥실트리요오드카본, 페네틸트리요오드카본, 2-노르보르닐트리요오드카본, 비닐트리요오드카본, 페닐트리요오드카본, 디메틸디클로로카본, 디에틸디클로로카본, 디-n-프로필디클로로카본, 디이소프로필디클로로카본, 디-n-부틸디클로로카본, 디-t-부틸디클로로카본, 디시클로헥실디클로로카본, 디페네틸디클로로카본, 디-2-노르보르닐디클로로카본, 디비닐디클로로카본, 디페닐디클로로카본, 디메틸디브로모카본, 디에틸디브로모카본, 디-n-프로필디브로모카본, 디이소프로필디브로모카본, 디-n-부틸디브로모카본, 디-t-부틸디브로모카본, 디시클로헥실디브로모카본, 디페네틸디브로모카본, 디-2-노르보르닐디브로모카본, 디비닐디브로모카본, 디페닐디브로모카본, 디메틸디요오드카본, 디에틸디요오드카본, 디-n-프로필요오드카본, 디이소프로필요오드카본, 디-n-부틸디요오드카본, 디-t-부틸디요오드카본, 디시클로헥실디요오드카본, 디페네틸디요오드카본, 디-2-노르보르닐디요오드카본, 디비닐디요오드카본, 디페닐디요오드카본, 트리메틸클로로카본, 트리에틸클로로카본, 트리-n-프로필클로로카본, 트리이소프로필클로로카본, 트리-n-부틸클로로카본, 트리-t-부틸클로로카본, 트리시클로헥실클로로카본, 트리페네틸클로로카본, 트리-2-노르보르닐클로로카본, 트리비닐클로로카본, 트리페닐클로로카본, 트리메틸브로모카본, 트리에틸브로모카본, 트리-n-프로필브로모카본, 트리이소프로필브로모카본, 트리-n-부틸브로모카본, 트리-t-부틸브로모카본, 트리시클로헥실브로모카본, 트리페네틸브로모카본, 트리-2-노르보르닐브로모카본, 트리비닐브로 모카본, 트리페닐브로모카본, 트리메틸요오드카본, 트리에틸요오드카본, 트리-n-프로필요오드카본, 트리이소프로필요오드카본, 트리-n-부틸요오드카본, 트리-t-부틸요오드카본, 트리시클로헥실요오드카본, 트리페네틸요오드카본, 트리-2-노르보르닐요오드카본, 트리비닐요오드카본, 트리페닐요오드카본 등의 탄소 화합물을 들 수 있다.
이들 화합물 1 중, 테트라클로로카본, 테트라브로모카본, 클로로포름, 브로모포름, 메틸트리클로로카본, 에틸트리클로로카본, 비닐트리클로로카본, 페닐트리클로로카본, 메틸트리브로모카본, 에틸트리브로모카본, 비닐트리브로모카본, 페닐트리브로모카본, 디클로로메탄, 디브로모에탄, 디요오드메탄, 디메틸디클로로카본, 디에틸디클로로카본, 디비닐디클로로카본, 디메틸디브로모카본, 디에틸디브로모카본, 디비닐디브로모카본 등을 바람직한 화합물로서 들 수 있다.
이들 화합물 1은 1종 단독으로도 사용할 수 있고, 2종 이상을 혼합하여 사용할 수도 있다.
1.1.2. 화합물 2
화학식 2로 표시되는 화합물(이하, "화합물 2"라 함)로는, 예를 들면 테트라클로로실란, 테트라브로모실란, 테트라요오드실란, 트리클로로실란, 트리브로모실란, 트리요오드실란, 메틸트리클로로실란, 에틸트리클로로실란, n-프로필트리클로로실란, 이소프로필트리클로로실란, n-부틸트리클로로실란, t-부틸트리클로로실란, 시클로헥실트리클로로실란, 페네틸트리클로로실란, 2-노르보르닐트리클로로실란, 비닐트리클로로실란, 페닐트리클로로실란, 메틸트리브로모실란, 에틸트리브로모실 란, n-프로필트리브로모실란, 이소프로필트리브로모실란, n-부틸트리브로모실란, t-부틸트리브로모실란, 시클로헥실트리브로모실란, 페네틸트리브로모실란, 2-노르보르닐트리브로모실란, 비닐트리브로모실란, 페닐트리브로모실란, 메틸트리요오드실란, 에틸트리요오드실란, n-프로필트리요오드실란, 이소프로필트리요오드실란, n-부틸트리요오드실란, t-부틸트리요오드실란, 시클로헥실트리요오드실란, 페네틸트리요오드실란, 2-노르보르닐트리요오드실란, 비닐트리요오드실란, 페닐트리요오드실란 등;
디메틸디클로로실란, 디에틸디클로로실란, 디-n-프로필디클로로실란, 디이소프로필디클로로실란, 디-n-부틸디클로로실란, 디-t-부틸디클로로실란, 디시클로헥실디클로로실란, 디페네틸디클로로실란, 디-2-노르보르닐디클로로실란, 디비닐디클로로실란, 디페닐디클로로실란, 디메틸디브로모실란, 디에틸디브로모실란, 디-n-프로필디브로모실란, 디이소프로필디브로모실란, 디-n-부틸디브로모실란, 디-t-부틸디브로모실란, 디시클로헥실디브로모실란, 디페네틸디브로모실란, 디-2-노르보르닐디브로모실란, 디비닐디브로모실란, 디페닐디브로모실란, 디메틸디요오드실란, 디에틸디요오드실란, 디-n-프로필디요오드실란, 디이소프로필디요오드실란, 디-n-부틸디요오드실란, 디-t-부틸디요오드실란, 디시클로헥실디요오드실란, 디페네틸디요오드실란, 디-2-노르보르닐디요오드실란, 디비닐디요오드실란, 디페닐디요오드실란, 트리메틸클로로실란, 트리에틸클로로실란, 트리-n-프로필클로로실란, 트리이소프로필클로로실란, 트리-n-부틸클로로실란, 트리-t-부틸클로로실란, 트리시클로헥실클로로실란, 트리페네틸클로로실란, 트리-2-노르보르닐클로로실란, 트리비닐클로 로실란, 트리페닐클로로실란, 트리메틸브로모실란, 트리에틸브로모실란, 트리-n-프로필브로모실란, 트리이소프로필브로모실란, 트리-n-부틸브로모실란, 트리-t-부틸브로모실란, 트리시클로헥실브로모실란, 트리페네틸브로모실란, 트리-2-노르보르닐브로모실란, 트리비닐브로모실란, 트리페닐브로모실란, 트리메틸요오드실란, 트리에틸요오드실란, 트리-n-프로필요오드실란, 트리이소프로필요오드실란, 트리-n-부틸요오드실란, 트리-t-부틸요오드실란, 트리시클로헥실요오드실란, 트리페네틸요오드실란, 트리-2-노르보르닐요오드실란, 트리비닐요오드실란, 트리페닐요오드실란 등;
테트라메톡시실란, 테트라에톡시실란, 테트라-n-프로폭시실란, 테트라-iso-프로폭시실란, 테트라-n-부톡시실란, 테트라-sec-부톡시실란, 테트라-tert-부톡시실란, 테트라페녹시실란, 트리메톡시실란, 트리에톡시실란, 트리-n-프로폭시실란, 트리-iso-프로폭시실란, 트리-n-부톡시실란, 트리-sec-부톡시실란, 트리-tert-부톡시실란, 트리페녹시실란, 플루오로트리메톡시실란, 플루오로트리에톡시실란, 플루오로트리-n-프로폭시실란, 플루오로트리-iso-프로폭시실란, 플루오로트리-n-부톡시실란, 플루오로트리-sec-부톡시실란, 플루오로트리-tert-부톡시실란, 플루오로트리페녹시실란 등;
메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-iso-프로폭시실란, 메틸트리-n-부톡시실란, 메틸트리-sec-부톡시실란, 메틸트리-tert-부톡시실란, 메틸트리페녹시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 에틸트리-n-프로폭시실란, 에틸트리-iso-프로폭시실란, 에틸트리-n-부톡시실란, 에 틸트리-sec-부톡시실란, 에틸트리-tert-부톡시실란, 에틸트리페녹시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 비닐트리-n-프로폭시실란, 비닐트리-iso-프로폭시실란, 비닐트리-n-부톡시실란, 비닐트리-sec-부톡시실란, 비닐트리-tert-부톡시실란, 비닐트리페녹시실란, n-프로필트리메톡시실란, n-프로필트리에톡시실란, n-프로필트리-n-프로폭시실란, n-프로필트리-iso-프로폭시실란, n-프로필트리-n-부톡시실란, n-프로필트리-sec-부톡시실란, n-프로필트리-tert-부톡시실란, n-프로필트리페녹시실란, i-프로필트리메톡시실란, i-프로필트리에톡시실란, i-프로필트리-n-프로폭시실란, i-프로필트리-iso-프로폭시실란, i-프로필트리-n-부톡시실란, i-프로필트리-sec-부톡시실란, i-프로필트리-tert-부톡시실란, i-프로필트리페녹시실란, n-부틸트리메톡시실란, n-부틸트리에톡시실란, n-부틸트리-n-프로폭시실란, n-부틸트리-iso-프로폭시실란, n-부틸트리-n-부톡시실란, n-부틸트리-sec-부톡시실란, n-부틸트리-tert-부톡시실란, n-부틸트리페녹시실란, sec-부틸트리메톡시실란, sec-부틸트리에톡시실란, sec-부틸트리-n-프로폭시실란, sec-부틸트리-iso-프로폭시실란, sec-부틸트리-n-부톡시실란, sec-부틸트리-sec-부톡시실란, sec-부틸트리-tert-부톡시실란, sec-부틸트리페녹시실란, t-부틸트리메톡시실란, t-부틸트리에톡시실란, t-부틸트리-n-프로폭시실란, t-부틸트리-iso-프로폭시실란, t-부틸트리-n-부톡시실란, t-부틸트리-sec-부톡시실란, t-부틸트리-tert-부톡시실란, t-부틸트리페녹시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 페닐트리-n-프로폭시실란, 페닐트리-iso-프로폭시실란, 페닐트리-n-부톡시실란, 페닐트리-sec-부톡시실란, 페닐트리-tert-부톡시실란, 페닐트리페녹시실란, 비닐트리메톡시실란, 비닐 트리에톡 시실란, γ-아미노프로필트리메톡시실란, γ-아미노프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란, γ-글리시독시프로필트리에톡시실란, γ-트리플루오로프로필트리메톡시실란, γ-트리플루오로프로필트리에톡시실란 등;
디메틸디메톡시실란, 디메틸디에톡시실란, 디메틸-디-n-프로폭시실란, 디메틸-디-iso-프로폭시실란, 디메틸-디-n-부톡시실란, 디메틸-디-sec-부톡시실란, 디메틸-디-tert-부톡시실란, 디메틸디페녹시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디에틸-디-n-프로폭시실란, 디에틸-디-iso-프로폭시실란, 디에틸-디-n-부톡시실란, 디에틸-디-sec-부톡시실란, 디에틸-디-tert-부톡시실란, 디에틸디페녹시실란, 디-n-프로필디메톡시실란, 디-n-프로필디에톡시실란, 디-n-프로필-디-n-프로폭시실란, 디-n-프로필-디-iso-프로폭시실란, 디-n-프로필-디-n-부톡시실란, 디-n-프로필-디-sec-부톡시실란, 디-n-프로필-디-tert-부톡시실란, 디-n-프로필-디-페녹시실란, 디-iso-프로필디메톡시실란, 디-iso-프로필디에톡시실란, 디-iso-프로필-디-n-프로폭시실란, 디-iso-프로필-디-iso-프로폭시실란, 디-iso-프로필-디-n-부톡시실란, 디-iso-프로필-디-sec-부톡시실란, 디-iso-프로필-디-tert-부톡시실란, 디-iso-프로필-디-페녹시실란, 디-n-부틸디메톡시실란, 디-n-부틸디에톡시실란, 디-n-부틸-디-n-프로폭시실란, 디-n-부틸-디-iso-프로폭시실란, 디-n-부틸-디-n-부톡시실란, 디-n-부틸-디-sec-부톡시실란, 디-n-부틸-디-tert-부톡시실란, 디-n-부틸-디-페녹시실란, 디-sec-부틸디메톡시실란, 디-sec-부틸디에톡시실란, 디-sec-부틸-디-n-프로폭시실란, 디-sec-부틸-디-iso-프로폭시실란, 디-sec-부틸-디-n-부톡시실란, 디-sec-부틸-디-sec-부톡시실란, 디-sec-부틸-디-tert-부톡시실란, 디-sec-부 틸-디-페녹시실란, 디-tert-부틸디메톡시실란, 디-tert-부틸디에톡시실란, 디-tert-부틸-디-n-프로폭시실란, 디-tert-부틸-디-iso-프로폭시실란, 디-tert-부틸-디-n-부톡시실란, 디-tert-부틸-디-sec-부톡시실란, 디-tert-부틸-디-tert-부톡시실란, 디-tert-부틸-디-페녹시실란, 디페닐디메톡시실란, 디페닐-디-에톡시실란, 디페닐-디-n-프로폭시실란, 디페닐-디-iso-프로폭시실란, 디페닐-디-n-부톡시실란, 디페닐-디-sec-부톡시실란, 디페닐-디-tert-부톡시실란, 디페닐디페녹시실란, 디비닐트리메톡시실란 등의 규소 화합물을 들 수 있다.
이들 화합물 2 중, 테트라클로로실란, 테트라브로모실란, 트리클로로실란, 트리브로모실란, 메틸트리클로로실란, 에틸트리클로로실란, 비닐트리클로로실란, 페닐트리클로로실란, 메틸트리브로모실란, 에틸트리브로모실란, 비닐트리브로모실란, 페닐트리브로모실란, 디클로로실란, 디브로모실란, 디요오드실란, 디메틸디클로로실란, 디에틸디클로로실란, 디비닐디클로로실란, 디페닐디클로로실란, 디메틸디브로모실란, 디에틸디브로모실란, 디비닐디브로모실란, 디페닐디브로모실란, 테트라메톡시실란, 테트라에톡시실란, 트리메톡시실란, 트리에톡시실란, 메틸트리메톡시실란, 메틸트리에톡시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 디메틸디메톡시실란, 디메틸디에톡시실란 등을 바람직한 화합물로서 들 수 있다.
이들 화합물 2는 1종 단독으로도 사용할 수 있고, 2종 이상을 혼합하여 사용할 수도 있다.
1.1.3. 화합물 3
화학식 3으로 표시되는 화합물(이하, "화합물 3"이라 함)로는, 클로로메틸트리클로로실란, 브로모메틸트리클로로실란, 요오드메틸트리클로로실란, 클로로메틸메틸디클로로실란, 클로로메틸에틸디클로로실란, 클로로메틸-n-프로필디클로로실란, 클로로메틸이소프로필디클로로실란, 클로로메틸-n-부틸디클로로실란, 클로로메틸-t-부틸디클로로실란, 클로로메틸시클로헥실디클로로실란, 클로로메틸페네틸디클로로실란, 클로로메틸비닐디클로로실란, 클로로메틸페닐디클로로실란, 브로모메틸메틸디클로로실란, 브로모메틸에틸디클로로실란, 브로모메틸-n-프로필디클로로실란, 브로모메틸이소프로필디클로로실란, 브로모메틸-n-부틸디클로로실란, 브로모메틸-t-부틸디클로로실란, 브로모메틸시클로헥실디클로로실란, 브로모메틸페네틸디클로로실란, 브로모메틸비닐디클로로실란, 브로모메틸페닐디클로로실란, 요오드메틸메틸디클로로실란, 요오드메틸에틸디클로로실란, 요오드메틸-n-프로필디클로로실란, 요오드메틸이소프로필디클로로실란, 요오드메틸-n-부틸디클로로실란, 요오드메틸-t-부틸디클로로실란, 요오드메틸시클로헥실디클로로실란, 요오드메틸페네틸디클로로실란, 요오드메틸비닐디클로로실란, 요오드메틸페닐디클로로실란, 클로로메틸디메틸클로로실란, 클로로메틸디에틸클로로실란, 클로로메틸디-n-프로필클로로실란, 클로로메틸디이소프로필클로로실란, 클로로메틸-n-디부틸클로로실란, 클로로메틸디-t-부틸클로로실란, 클로로메틸디시클로헥실클로로실란, 클로로메틸디페네틸클로로실란, 클로로메틸디비닐클로로실란, 클로로메틸디페닐클로로실란, 브로모메틸디메틸클로로실란, 브로모메틸디에틸클로로실란, 브로모메틸디-n-프로필클로로실란, 브로모메틸디이소프로필클로로실란, 브로모메틸디-n-부틸클로로실란, 브로모메 틸디-t-부틸클로로실란, 브로모메틸디시클로헥실클로로실란, 브로모메틸디페네틸클로로실란, 브로모메틸디비닐클로로실란, 브로모메틸디페닐클로로실란, 요오드메틸디메틸클로로실란, 요오드메틸디에틸클로로실란, 요오드메틸디-n-프로필클로로실란, 요오드메틸디이소프로필클로로실란, 요오드메틸디-n-부틸클로로실란, 요오드메틸디-t-부틸클로로실란, 요오드메틸디시클로헥실클로로실란, 요오드메틸디페네틸클로로실란, 요오드메틸디비닐클로로실란, 요오드메틸디페닐클로로실란 등;
(1-클로로에틸)트리클로로실란, (1-클로로프로필)트리클로로실란, (2-클로로-2-프로필)트리클로로실란, (1-클로로부틸)트리클로로실란, (2-클로로-2-부틸)트리클로로실란, (3-클로로-3-펜틸)트리클로로실란, (1-클로로-2-프로페닐)트리클로로실란, (α-클로로벤질)트리클로로실란, 디클로로메틸트리클로로실란, 트리클로로메틸트리클로로실란, (1-클로로에틸)메틸디클로로실란, (1-클로로프로필)메틸디클로로실란, (2-클로로-2-프로필)메틸디클로로실란, (1-클로로부틸)메틸디클로로실란, (2-클로로-2-부틸)메틸디클로로실란, (3-클로로-3-펜틸)메틸디클로로실란, (1-클로로-2-프로페닐)메틸디클로로실란, (α-클로로벤질)메틸디클로로실란, 디클로로메틸메틸디클로로실란, 트리클로로메틸메틸디클로로실란, (1-클로로에틸)디메틸클로로실란, (1-클로로프로필)디메틸클로로실란, (2-클로로-2-프로필)디메틸클로로실란, (1-클로로부틸)디메틸클로로실란, (2-클로로-2-부틸)디메틸클로로실란, (3-클로로-3-펜틸)디메틸클로로실란, (1-클로로-2-프로페닐)디메틸클로로실란, (α-클로로벤질)디메틸클로로실란, 디클로로메틸디메틸클로로실란, 트리클로로메틸디메틸클로로실란 등;
클로로메틸트리메톡시실란, 브로모메틸트리메톡시실란, 요오드메틸트리메톡시실란, 클로로메틸메틸디메톡시실란, 클로로메틸에틸디메톡시실란, 클로로메틸-n-프로필디메톡시실란, 클로로메틸이소프로필디메톡시실란, 클로로메틸-n-부틸디메톡시실란, 클로로메틸-t-부틸디메톡시실란, 클로로메틸시클로헥실디메톡시실란, 클로로메틸페네틸디메톡시실란, 클로로메틸비닐디메톡시실란, 클로로메틸페닐디메톡시실란, 브로모메틸메틸디메톡시실란, 브로모메틸에틸디메톡시실란, 브로모메틸-n-프로필디메톡시실란, 브로모메틸이소프로필디메톡시실란, 브로모메틸-n-부틸디메톡시실란, 브로모메틸-t-부틸디메톡시실란, 브로모메틸시클로헥실디메톡시실란, 브로모메틸페네틸디메톡시실란, 브로모메틸비닐디메톡시실란, 브로모메틸페닐디메톡시실란, 요오드메틸메틸디메톡시실란, 요오드메틸에틸디메톡시실란, 요오드메틸-n-프로필디메톡시실란, 요오드메틸이소프로필디메톡시실란, 요오드메틸-n-부틸디메톡시실란, 요오드메틸-t-부틸디메톡시실란, 요오드메틸시클로헥실디메톡시실란, 요오드메틸페네틸디메톡시실란, 요오드메틸비닐디메톡시실란, 요오드메틸페닐디메톡시실란, 클로로메틸디메틸메톡시실란, 클로로메틸디에틸메톡시실란, 클로로메틸디-n-프로필메톡시실란, 클로로메틸디이소프로필메톡시실란, 클로로메틸-n-디부틸메톡시실란, 클로로메틸디-t-부틸메톡시실란, 클로로메틸디시클로헥실메톡시실란, 클로로메틸디페네틸메톡시실란, 클로로메틸디비닐메톡시실란, 클로로메틸디페닐메톡시실란, 브로모메틸디메틸메톡시실란, 브로모메틸디에틸메톡시실란, 브로모메틸디-n-프로필메톡시실란, 브로모메틸디이소프로필메톡시실란, 브로모메틸디-n-부틸메톡시실란, 브로모메틸디-t-부틸메톡시실란, 브로모메틸디시클로헥실메톡시실란, 브로모메틸디페 네틸메톡시실란, 브로모메틸디비닐메톡시실란, 브로모메틸디페닐메톡시실란, 요오드메틸디메틸메톡시실란, 요오드메틸디에틸메톡시실란, 요오드메틸디-n-프로필메톡시실란, 요오드메틸디이소프로필메톡시실란, 요오드메틸디-n-부틸메톡시실란, 요오드메틸디-t-부틸메톡시실란, 요오드메틸디시클로헥실메톡시실란, 요오드메틸디페네틸메톡시실란, 요오드메틸디비닐메톡시실란, 요오드메틸디페닐메톡시실란 등;
클로로메틸트리에톡시실란, 브로모메틸트리에톡시실란, 요오드메틸트리에톡시실란, 클로로메틸메틸디에톡시실란, 클로로메틸에틸디에톡시실란, 클로로메틸-n-프로필디에톡시실란, 클로로메틸이소프로필디에톡시실란, 클로로메틸-n-부틸디에톡시실란, 클로로메틸-t-부틸디에톡시실란, 클로로메틸시클로헥실디에톡시실란, 클로로메틸페네틸디에톡시실란, 클로로메틸비닐디에톡시실란, 클로로메틸페닐디에톡시실란, 브로모메틸메틸디에톡시실란, 브로모메틸에틸디에톡시실란, 브로모메틸-n-프로필디에톡시실란, 브로모메틸이소프로필디에톡시실란, 브로모메틸-n-부틸디에톡시실란, 브로모메틸-t-부틸디에톡시실란, 브로모메틸시클로헥실디에톡시실란, 브로모메틸페네틸디에톡시실란, 브로모메틸비닐디에톡시실란, 브로모메틸페닐디에톡시실란, 요오드메틸메틸디에톡시실란, 요오드메틸에틸디에톡시실란, 요오드메틸-n-프로필디에톡시실란, 요오드메틸이소프로필디에톡시실란, 요오드메틸-n-부틸디에톡시실란, 요오드메틸-t-부틸디에톡시실란, 요오드메틸시클로헥실디에톡시실란, 요오드메틸페네틸디에톡시실란, 요오드메틸비닐디에톡시실란, 요오드메틸페닐디에톡시실란, 클로로메틸디메틸에톡시실란, 클로로메틸디에틸에톡시실란, 클로로메틸디-n-프로필에톡시실란, 클로로메틸디이소프로필에톡시실란, 클로로메틸-n-디부틸에톡시실란, 클로로메틸디-t-부틸에톡시실란, 클로로메틸디시클로헥실에톡시실란, 클로로메틸디페네틸에톡시실란, 클로로메틸디비닐에톡시실란, 클로로메틸디페닐에톡시실란, 브로모메틸디메틸에톡시실란, 브로모메틸디에틸에톡시실란, 브로모메틸디-n-프로필에톡시실란, 브로모메틸디이소프로필에톡시실란, 브로모메틸디-n-부틸에톡시실란, 브로모메틸디-t-부틸에톡시실란, 브로모메틸디시클로헥실에톡시실란, 브로모메틸디페네틸에톡시실란, 브로모메틸디비닐에톡시실란, 브로모메틸디페닐에톡시실란, 요오드메틸디메틸에톡시실란, 요오드메틸디에틸에톡시실란, 요오드메틸디-n-프로필에톡시실란, 요오드메틸디이소프로필에톡시실란, 요오드메틸디-n-부틸에톡시실란, 요오드메틸디-t-부틸에톡시실란, 요오드메틸디시클로헥실에톡시실란, 요오드메틸디페네틸에톡시실란, 요오드메틸디비닐에톡시실란, 요오드메틸디페닐에톡시실란 등;
클로로메틸트리-n-프로폭시실란, 브로모메틸트리-n-프로폭시실란, 요오드메틸트리-n-프로폭시실란, 클로로메틸메틸디-n-프로폭시실란, 클로로메틸에틸디-n-프로폭시실란, 클로로메틸-n-프로필디-n-프로폭시실란, 클로로메틸이소프로필디-n-프로폭시실란, 클로로메틸-n-부틸디-n-프로폭시실란, 클로로메틸-t-부틸디-n-프로폭시실란, 클로로메틸시클로헥실디-n-프로폭시실란, 클로로메틸페네틸디-n-프로폭시실란, 클로로메틸비닐디-n-프로폭시실란, 클로로메틸페닐디-n-프로폭시실란, 브로모메틸메틸디-n-프로폭시실란, 브로모메틸에틸디-n-프로폭시실란, 브로모메틸-n-프로필디-n-프로폭시실란, 브로모메틸이소프로필디-n-프로폭시실란, 브로모메틸-n-부틸디-n-프로폭시실란, 브로모메틸-t-부틸디-n-프로폭시실란, 브로모메틸시클로헥실디-n-프로폭시실란, 브로모메틸페네틸디-n-프로폭시실란, 브로모메틸비닐디-n-프로 폭시실란, 브로모메틸페닐디-n-프로폭시실란, 요오드메틸메틸디-n-프로폭시실란, 요오드메틸에틸디-n-프로폭시실란, 요오드메틸-n-프로필디-n-프로폭시실란, 요오드메틸이소프로필디-n-프로폭시실란, 요오드메틸-n-부틸디-n-프로폭시실란, 요오드메틸-t-부틸디-n-프로폭시실란, 요오드메틸시클로헥실디-n-프로폭시실란, 요오드메틸페네틸디-n-프로폭시실란, 요오드메틸비닐디-n-프로폭시실란, 요오드메틸페닐디-n-프로폭시실란, 클로로메틸디메틸-n-프로폭시실란, 클로로메틸디에틸-n-프로폭시실란, 클로로메틸디-n-프로필-n-프로폭시실란, 클로로메틸디이소프로필-n-프로폭시실란, 클로로메틸-n-부틸-n-프로폭시실란, 클로로메틸디-t-부틸-n-프로폭시실란, 클로로메틸디시클로헥실-n-프로폭시실란, 클로로메틸디페네틸-n-프로폭시실란, 클로로메틸디비닐-n-프로폭시실란, 클로로메틸디페닐-n-프로폭시실란, 브로모메틸디메틸-n-프로폭시실란, 브로모메틸디에틸-n-프로폭시실란, 브로모메틸디-n-프로필-n-프로폭시실란, 브로모메틸디이소프로필-n-프로폭시실란, 브로모메틸디-n-부틸-n-프로폭시실란, 브로모메틸디-t-부틸-n-프로폭시실란, 브로모메틸디시클로헥실-n-프로폭시실란, 브로모메틸디페네틸-n-프로폭시실란, 브로모메틸디비닐-n-프로폭시실란, 브로모메틸디페닐-n-프로폭시실란, 요오드메틸디메틸-n-프로폭시실란, 요오드메틸디에틸-n-프로폭시실란, 요오드메틸디-n-프로필-n-프로폭시실란, 요오드메틸디이소프로필-n-프로폭시실란, 요오드메틸디-n-부틸-n-프로폭시실란, 요오드메틸디-t-부틸-n-프로폭시실란, 요오드메틸디시클로헥실-n-프로폭시실란, 요오드메틸디페네틸-n-프로폭시실란, 요오드메틸디비닐-n-프로폭시실란, 요오드메틸디페닐-n-프로폭시실란 등;
클로로메틸트리이소프로폭시실란, 브로모메틸트리이소프로폭시실란, 요오드메틸트리이소프로폭시실란, 클로로메틸메틸디이소프로폭시실란, 클로로메틸에틸디이소프로폭시실란, 클로로메틸-n-프로필디이소프로폭시실란, 클로로메틸이소프로필디이소프로폭시실란, 클로로메틸-n-부틸디이소프로폭시실란, 클로로메틸-t-부틸디이소프로폭시실란, 클로로메틸시클로헥실디이소프로폭시실란, 클로로메틸페네틸디이소프로폭시실란, 클로로메틸비닐디이소프로폭시실란, 클로로메틸페닐디이소프로폭시실란, 브로모메틸메틸디이소프로폭시실란, 브로모메틸에틸디이소프로폭시실란, 브로모메틸-n-프로필디이소프로폭시실란, 브로모메틸이소프로필디이소프로폭시실란, 브로모메틸-n-부틸디이소프로폭시실란, 브로모메틸-t-부틸디이소프로폭시실란, 브로모메틸시클로헥실디이소프로폭시실란, 브로모메틸페네틸디이소프로폭시실란, 브로모메틸비닐디이소프로폭시실란, 브로모메틸페닐디이소프로폭시실란, 요오드메틸메틸디이소프로폭시실란, 요오드메틸에틸디이소프로폭시실란, 요오드메틸-n-프로필디이소프로폭시실란, 요오드메틸이소프로필디이소프로폭시실란, 요오드메틸-n-부틸디이소프로폭시실란, 요오드메틸-t-부틸디이소프로폭시실란, 요오드메틸시클로헥실디이소프로폭시실란, 요오드메틸페네틸디이소프로폭시실란, 요오드메틸비닐디이소프로폭시실란, 요오드메틸페닐디이소프로폭시실란, 클로로메틸디메틸이소프로폭시실란, 클로로메틸디에틸이소프로폭시실란, 클로로메틸디-n-프로필이소프로폭시실란, 클로로메틸디이소프로필이소프로폭시실란, 클로로메틸-n-디부틸이소프로폭시실란, 클로로메틸디-t-부틸이소프로폭시실란, 클로로메틸디시클로헥실이소프로폭시실란, 클로로메틸디페네틸이소프로폭시실란, 클로로메틸디비닐이소프로폭시실란, 클 로로메틸디페닐이소프로폭시실란, 브로모메틸디메틸이소프로폭시실란, 브로모메틸디에틸이소프로폭시실란, 브로모메틸디-n-프로필이소프로폭시실란, 브로모메틸디이소프로필이소프로폭시실란, 브로모메틸디-n-부틸이소프로폭시실란, 브로모메틸디-t-부틸이소프로폭시실란, 브로모메틸디시클로헥실이소프로폭시실란, 브로모메틸디페네틸이소프로폭시실란, 브로모메틸디비닐이소프로폭시실란, 브로모메틸디페닐이소프로폭시실란, 요오드메틸디메틸이소프로폭시실란, 요오드메틸디에틸이소프로폭시실란, 요오드메틸디-n-프로필이소프로폭시실란, 요오드메틸디이소프로필이소프로폭시실란, 요오드메틸디-n-부틸이소프로폭시실란, 요오드메틸디-t-부틸이소프로폭시실란, 요오드메틸디시클로헥실이소프로폭시실란, 요오드메틸디페네틸이소프로폭시실란, 요오드메틸디비닐이소프로폭시실란, 요오드메틸디페닐이소프로폭시실란 등의 규소 화합물을 들 수 있다.
이들 화합물 3 중, 클로로메틸트리클로로실란, 브로모메틸트리클로로실란, 클로로메틸메틸디클로로실란, 클로로메틸에틸디클로로실란, 클로로메틸비닐디클로로실란, 클로로메틸페닐디클로로실란, 브로모메틸메틸디클로로실란, 브로모메틸비닐디클로로실란, 클로로메틸디메틸클로로실란, 클로로메틸디비닐클로로실란, 브로모메틸디메틸클로로실란, (1-클로로에틸)트리클로로실란, (1-클로로프로필)트리클로로실란, 클로로메틸트리메톡시실란, 브로모메틸트리메톡시실란, 클로로메틸메틸디메톡시실란, 클로로메틸비닐디메톡시실란, 클로로메틸페닐디메톡시실란, 브로모메틸메틸디메톡시실란, 브로모메틸비닐디메톡시실란, 브로모메틸페닐디메톡시실란, 클로로메틸디메틸메톡시실란, 클로로메틸디비닐메톡시실란, 클로로메틸디페닐메톡 시실란, 브로모메틸디메틸메톡시실란, 브로모메틸디이소프로필메톡시실란, 클로로메틸트리에톡시실란, 브로모메틸트리에톡시실란, 클로로메틸메틸디에톡시실란, 클로로메틸에틸디에톡시실란, 클로로메틸비닐디에톡시실란, 클로로메틸페닐디에톡시실란, 브로모메틸메틸디에톡시실란, 브로모메틸비닐디에톡시실란, 브로모메틸페닐디에톡시실란, 클로로메틸디메틸에톡시실란, 클로로메틸디에틸에톡시실란, 브로모메틸디비닐에톡시실란, 클로로메틸트리이소프로폭시실란, 브로모메틸트리이소프로폭시실란 등을 바람직한 화합물로서 들 수 있다.
이들 화합물 3은 1종 단독으로도 사용할 수 있고, 2종 이상을 혼합하여 사용할 수도 있다.
1.2. (A) 폴리카르보실란의 제조
본 발명에서, 상술한 바와 같이, (A) 폴리카르보실란은 하기 중합체 (I)이다.
(I) (a) 화합물 1과, (b) 화합물 2 및 화합물 3으로부터 선택되는 1종 이상을 유기 용매 중에서 알칼리 금속 및 알칼리 토금속 중 하나 이상의 존재하에서 반응시켜 얻어지는 중합체(중합체 (I)).
중합체 (I)에서, 화합물 1과, 화합물 2 및(또는) 화합물 3의 사용 비율[화합물 1/(화합물 2 및(또는) 화합물 3)]은 몰비로, 바람직하게는 0.01 내지 100, 보다 바람직하게는 0.1 내지 10, 특히 바람직하게는 0.5 내지 5이다. 몰비가 이 범위에 있으면 생성되는 중합체의 중합도를 향상시킬 수 있다.
본 발명에서 사용할 수 있는 알칼리 금속으로는 리튬, 칼륨, 나트륨을 들 수 있고, 알칼리 토금속으로는 마그네슘을 들 수 있지만, 본 발명에서는 마그네슘을 사용하는 것이 가장 바람직하다.
알칼리 금속 및 알칼리 토금속은 화합물 1과, 화합물 2 및(또는) 화합물 3으로부터 환원적으로 할로겐 원자 또는 알콕시기를 이탈시켜 탄소-규소 결합을 형성하기 위해서 사용하는 것이고, 그 사용량은 바람직하게는, 화합물 1 및 화합물 2 및(또는) 화합물 3의 탄소-할로겐 결합 및 탄소-알콕시기 결합의 총량에 대하여 1.0 내지 1.5 몰 당량이다.
중합체 (I)의 제조 방법에서는, 필요에 따라서 외부로부터 반응액에 초음파를 조사함으로써 반응을 촉진시킬 수 있다. 여기서 사용되는 초음파의 진동수로는 10 내지 70 KHz 정도인 것이 바람직하다.
중합체 (I)의 제조에서 사용하는 유기 용매로는, 에테르계 용매를 바람직한 것으로서 사용할 수 있다. 통상의 키핑(Kipping) 반응에서 사용하는 탄화수소계 용매로는 목적으로 하는 가용성 규소 올리고머의 수율이 낮아지기 쉽다.
에테르계 용매로는, 예를 들면 디에틸에테르, 디-n-프로필에테르, 디이소프로필에테르, 디부틸에테르, 에틸프로필에테르, 아니솔, 페네톨, 디페닐에테르, 디에틸렌글리콜 디메틸에테르, 디에틸렌글리콜 디에틸에테르, 디에틸렌글리콜 디부틸에테르, 디에틸렌글리콜 메틸에틸에테르, 디프로필렌글리콜 디메틸에테르, 디프로필렌글리콜 디에틸에테르, 디프로필렌글리콜 디부틸에테르, 디프로필렌글리콜 메틸에틸에테르, 에틸렌글리콜 디메틸에테르, 에틸렌글리콜 디에틸에테르, 에틸렌글리콜 디부틸에테르, 에틸렌글리콜 메틸에틸에테르, 프로필렌글리콜 디메틸에테르, 프 로필렌글리콜 디에틸에테르, 프로필렌글리콜 디부틸에테르, 프로필렌글리콜 메틸에틸에테르, 테트라히드로푸란, 디옥산 등을 들 수 있다. 이들 중에서, 생성되는 중합체의 용해성의 관점에서, 디에틸에테르, 테트라히드로푸란, 에틸렌글리콜 디메틸에테르, 에틸렌글리콜 디에틸에테르 등이 바람직하다.
이들 에테르계 용매는 수분을 미리 제거해두는 것이 바람직하다. 수분의 제거법으로는, 나트륨-벤조페논케틸의 존재하에서의 탈기 증류법 등이 바람직하다. 이들 용매의 사용량은 특별히 한정되지 않지만, 상기 화합물 1 및 화합물 2 및(또는) 화합물 3의 총량에 대하여, 바람직하게는 1 내지 30 중량부이고, 보다 바람직하게는 2 내지 20 중량부이다.
중합체 (I)의 반응 온도는, 바람직하게는 0 내지 150 ℃, 보다 바람직하게는 30 내지 100 ℃이다. 반응 온도가 0 ℃ 미만이면 반응 속도가 느려서 생산성이 떨어지고, 반응 온도가 150 ℃보다 높은 경우에는 반응이 복잡하게 되어 얻어지는 중합체의 용해성이 저하되기 쉬워진다. 또한, 반응은 통상 아르곤이나 질소 등의 불활성 가스 중에서 행하는 것이 바람직하다.
본 발명에서는, 상기한 방법에 의해 얻어진 중합체 (I)를, (i) 중합체 (I) 중 Y가 할로겐 원자를 갖는 경우에는 추가로 유기 용매 중에서 알코올 또는 유기산과 반응시킬 수도 있으며, (ii) 유기 용매 중에서 환원제와 반응시킬 수도 있다. 상기 (i)의 방법에서는, 분자 말단 또는 측쇄에 미반응된 가수분해성 할로겐 원자를 갖는 중합체 (I)를 알코올 또는 유기산과 반응시킴으로써 할로겐 원자를 보다 안정적인 알콕시기 또는 에스테르기로 치환 처리할 수 있다.
알코올로는, 메탄올, 에탄올, n-프로판올, i-프로판올, n-부탄올, i-부탄올, sec-부탄올, t-부탄올, n-펜탄올, i-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 모노알코올;
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 알코올;
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 등을 들 수 있다.
유기산으로는, 아세트산, 프로피온산, 부탄산, 펜탄산, 헥산산, 헵탄산, 옥탄산, 노난산, 데칸산, 옥살산, 말레산, 메틸말론산, 아디프산, 세박산, 갈산, 부티르산, 메리트산, 아라키돈산, 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, 글루타르산 등을 들 수 있다.
알코올 또는 산은 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다.
알코올 또는 산의 사용량은 각각의 히드록실기가 잔류하는 중합체의 할로겐 원자에 대해서 적어도 당량이고, 보다 바람직하게는 1.0 내지 4.0배 당량이다. 또한, 이 때에 사용되는 용매로는, 사용되는 알코올 또는 산과 반응하지 않는 용매이면 특별히 한정되지 않지만, 통상 방향족계 용매가 바람직하고, 예를 들면 벤젠, 톨루엔, 크실렌, 메시틸렌 등을 들 수 있다. 이들은 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. 또한, 이 반응시에 생성되는 할로겐화수소의 포착을 위해, 할로겐화수소와 쌍을 이뤄 염을 생성하며, 활성 수소를 갖지 않는 유기 아민의 첨가를 행하는 것이 바람직하다. 이러한 유기 아민의 구체예로는, 피리딘, 피롤, 피콜린, 디아자비시클로옥탄, 디아자비시클로노난, 디아자비시클로운데센, 트리메틸아민, 트리에틸아민, 트리프로필아민, 트리부틸아민 등을 들 수 있다. 이들 알칼리 촉매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
상기 (ii)의 방법에서는, 분자 말단에 미반응된 가수분해성 할로겐 원자를 갖는 중합체 (I) 또는 상기 (i)의 방법에 의해 얻어진 중합체를 환원제로 환원시킴으로써 규소 원자 상의 치환기를 안정적인 수소 원자로 치환 처리할 수 있다.
이러한 환원제로는, 예를 들면 LiAlH4, NaH, LiBu3BH, (C5H11)2BH, B2H6, NaBH4, Zn(BH4)2, NaBH3CN, Bu2AlH, Li(OBu)3AlH 등을 들 수 있고, LiAlH4, NaH, B2H6, NaBH4를 보다 바람직한 예로서 들 수 있다.
환원제의 사용량은, 환원제 중 수소 원자가 잔류하는 중합체의 할로겐 원자에 대해서 적어도 당량이며, 바람직하게는 1.0 내지 4.0배 당량이다. 또한, 이 때에 사용하는 용매로는 환원제와 반응하지 않는 용매이면 특별히 한정되지 않지만, 통상 에테르계 용매가 바람직하고, 앞서 예시한 에테르계 용매와 동일한 것을 사용할 수 있다. 이들은 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다.
이 때의 반응 온도는 바람직하게는 -78 ℃ 내지 +60 ℃이다. 반응 온도가 -78 ℃ 미만이면 반응이 느려서 생산성이 떨어지며, +60 ℃보다 높은 경우에는 반응 생성물의 용해성이 낮아지고, 중합체의 생성 수율이 낮아지기 쉽다. 또한, 반응은 통상 아르곤이나 질소 등의 불활성 가스 중에서 행하는 것이 바람직하다.
1.3. 중합체의 제조
본 발명의 중합체는, 상술한 바와 같이, 상기 (A) 폴리카르보실란의 존재하에 (B) 가수분해성기 함유 중합체를 가수분해 축합하여 얻어진다. 본 발명에서 "가수분해성기"란, 본 발명의 중합체의 제조시에 가수분해될 수 있는 기를 말한다. 가수분해성기의 구체예로는 특별히 한정되지 않지만, 예를 들면 실리콘 원자에 결 합한 수소 원자, 할로겐 원자, 히드록시기, 알콕시기, 아실옥시기, 술폰기, 메탄술폰기, 및 트리플루오로메탄술폰기를 들 수 있다.
(B) 가수분해성기 함유 중합체는, 하기 화학식 4로 표시되는 화합물 및 하기 화학식 5로 표시되는 화합물의 군으로부터 선택된 1종 이상의 실란 화합물일 수 있다.
<화학식 4>
R5 aSiX4 -a
식 중, R5는 수소 원자, 불소 원자 또는 1가의 유기기를 나타내고, X는 할로겐 원자 또는 알콕시기를 나타내며, a는 0 내지 3의 정수를 나타낸다.
<화학식 5>
R6 bY3 - bSi-(R8)d-SiZ3 - cR7 c
식 중, R6, R7은 동일하거나 상이하고, 각각 1가의 유기기를 나타내며, b 및 c는 동일하거나 상이하고, 0 내지 2의 정수를 나타내며, R8은 산소 원자, 페닐렌기 또는 -(CH2)e-로 표시되는 기(여기서, e는 1 내지 6의 정수임)를 나타내고, Y 및 Z는 동일하거나 상이하며, 할로겐 원자 또는 알콕시기를 나타내고, d는 0 또는 1을 나타낸다.
1.3.1. 화학식 4로 표시되는 화합물
상기 화학식 4에서, R5는 수소 원자, 불소 원자 또는 1가의 유기기이다. 1가의 유기기로는, 알킬기, 아릴기, 알릴기, 글리시딜기, 비닐기 등을 들 수 있다. 또한, 화학식 4에서, R5는 1가의 유기기, 특히 알킬기 또는 페닐기인 것이 바람직하다.
여기서 알킬기로는, 메틸기, 에틸기, 프로필기, 부틸기 등을 들 수 있고, 바람직하게는 탄소수 1 내지 5이다. 이들 알킬기는 쇄상이거나, 분지하고 있을 수도 있으며, 수소 원자, 불소 원자, 아미노기 등으로 치환될 수도 있다.
아릴기로는, 페닐기, 나프틸기, 메틸페닐기, 에틸페닐기, 클로로페닐기, 브로모페닐기, 플루오로페닐기 등을 들 수 있다.
또한, X의 알콕시기의 탄화수소 부위에 대해서는, R5의 1가의 유기기로서 예를 들었던 것을 그대로 적용시킬 수 있다.
화학식 4로 표시되는 화합물(이하, "화합물 4"라고도 함)의 구체예로는, 테트라메톡시실란, 테트라에톡시실란, 테트라-n-프로폭시실란, 테트라-iso-프로폭시실란, 테트라-n-부톡시실란, 테트라-sec-부톡시실란, 테트라-tert-부톡시실란, 테트라페녹시실란, 트리메톡시실란, 트리에톡시실란, 트리-n-프로폭시실란, 트리-iso-프로폭시실란, 트리-n-부톡시실란, 트리-sec-부톡시실란, 트리-tert-부톡시실란, 트리페녹시실란, 플루오로트리메톡시실란, 플루오로트리에톡시실란, 플루오로트리-n-프로폭시실란, 플루오로트리-iso-프로폭시실란, 플루오로트리-n-부톡시실란, 플루오로트리-sec-부톡시실란, 플루오로트리-tert-부톡시실란, 플루오로트리페 녹시실란 등;
메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-iso-프로폭시실란, 메틸트리-n-부톡시실란, 메틸트리-sec-부톡시실란, 메틸트리-tert-부톡시실란, 메틸트리페녹시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 에틸트리-n-프로폭시실란, 에틸트리-iso-프로폭시실란, 에틸트리-n-부톡시실란, 에틸트리-sec-부톡시실란, 에틸트리-tert-부톡시실란, 에틸트리페녹시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 비닐트리-n-프로폭시실란, 비닐트리-iso-프로폭시실란, 비닐트리-n-부톡시실란, 비닐트리-sec-부톡시실란, 비닐트리-tert-부톡시실란, 비닐트리페녹시실란, n-프로필트리메톡시실란, n-프로필트리에톡시실란, n-프로필트리-n-프로폭시실란, n-프로필트리-iso-프로폭시실란, n-프로필트리-n-부톡시실란, n-프로필트리-sec-부톡시실란, n-프로필트리-tert-부톡시실란, n-프로필트리페녹시실란, i-프로필트리메톡시실란, i-프로필트리에톡시실란, i-프로필트리-n-프로폭시실란, i-프로필트리-iso-프로폭시실란, i-프로필트리-n-부톡시실란, i-프로필트리-sec-부톡시실란, i-프로필트리-tert-부톡시실란, i-프로필트리페녹시실란, n-부틸트리메톡시실란, n-부틸트리에톡시실란, n-부틸트리-n-프로폭시실란, n-부틸트리-iso-프로폭시실란, n-부틸트리-n-부톡시실란, n-부틸트리-sec-부톡시실란, n-부틸트리-tert-부톡시실란, n-부틸트리페녹시실란, sec-부틸트리메톡시실란, sec-부틸트리에톡시실란, sec-부틸-트리-n-프로폭시실란, sec-부틸-트리-iso-프로폭시실란, sec-부틸-트리-부톡시실란, sec-부틸-트리-sec-부톡시실란, sec-부틸-트리-tert-부톡시실란, sec-부틸-트리페녹시실란, t-부틸트리메톡시실란, t-부틸트리 에톡시실란, t-부틸트리-n-프로폭시실란, t-부틸트리-iso-프로폭시실란, t-부틸트리-n-부톡시실란, t-부틸트리-sec-부톡시실란, t-부틸트리-tert-부톡시실란, t-부틸트리페녹시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 페닐트리-n-프로폭시실란, 페닐트리-iso-프로폭시실란, 페닐트리-n-부톡시실란, 페닐트리-sec-부톡시실란, 페닐트리-tert-부톡시실란, 페닐트리페녹시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, γ-아미노프로필트리메톡시실란, γ-아미노프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란, γ-글리시독시프로필트리에톡시실란, γ-트리플루오로프로필트리메톡시실란, γ-트리플루오로프로필트리에톡시실란 등;
디메틸디메톡시실란, 디메틸디에톡시실란, 디메틸-디-n-프로폭시실란, 디메틸-디-iso-프로폭시실란, 디메틸-디-n-부톡시실란, 디메틸-디-sec-부톡시실란, 디메틸-디-tert-부톡시실란, 디메틸디페녹시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디에틸-디-n-프로폭시실란, 디에틸-디-iso-프로폭시실란, 디에틸-디-n-부톡시실란, 디에틸-디-sec-부톡시실란, 디에틸-디-tert-부톡시실란, 디에틸디페녹시실란, 디-n-프로필디메톡시실란, 디-n-프로필디에톡시실란, 디-n-프로필-디-n-프로폭시실란, 디-n-프로필-디-iso-프로폭시실란, 디-n-프로필-디-n-부톡시실란, 디-n-프로필-디-sec-부톡시실란, 디-n-프로필-디-tert-부톡시실란, 디-n-프로필-디-페녹시실란, 디-iso-프로필디메톡시실란, 디-iso-프로필디에톡시실란, 디-iso-프로필-디-n-프로폭시실란, 디-iso-프로필-디-iso-프로폭시실란, 디-iso-프로필-디-n-부톡시실란, 디-iso-프로필-디-sec-부톡시실란, 디-iso-프로필-디-tert-부톡시실란, 디-iso-프로필-디-페녹시실란, 디-n-부틸디메톡시실란, 디-n-부틸디에톡시실란, 디- n-부틸-디-n-프로폭시실란, 디-n-부틸-디-iso-프로폭시실란, 디-n-부틸-디-n-부톡시실란, 디-n-부틸-디-sec-부톡시실란, 디-n-부틸-디-tert-부톡시실란, 디-n-부틸-디-페녹시실란, 디-sec-부틸디메톡시실란, 디-sec-부틸디에톡시실란, 디-sec-부틸-디-n-프로폭시실란, 디-sec-부틸-디-iso-프로폭시실란, 디-sec-부틸-디-n-부톡시실란, 디-sec-부틸-디-sec-부톡시실란, 디-sec-부틸-디-tert-부톡시실란, 디-sec-부틸-디-페녹시실란, 디-tert-부틸디메톡시실란, 디-tert-부틸디에톡시실란, 디-tert-부틸-디-n-프로폭시실란, 디-tert-부틸-디-iso-프로폭시실란, 디-tert-부틸-디-n-부톡시실란, 디-tert-부틸-디-sec-부톡시실란, 디-tert-부틸-디-tert-부톡시실란, 디-tert-부틸-디-페녹시실란, 디페닐디메톡시실란, 디페닐-디-에톡시실란, 디페닐-디-n-프로폭시실란, 디페닐-디-iso-프로폭시실란, 디페닐-디-n-부톡시실란, 디페닐-디-sec-부톡시실란, 디페닐-디-tert-부톡시실란, 디페닐디페녹시실란, 디비닐트리메톡시실란 등;
테트라클로로실란, 테트라브로모실란, 테트라요오드실란, 트리클로로실란, 트리브로모실란, 트리요오드실란, 메틸트리클로로실란, 에틸트리클로로실란, n-프로필트리클로로실란, 이소프로필트리클로로실란, n-부틸트리클로로실란, t-부틸트리클로로실란, 시클로헥실트리클로로실란, 페네틸트리클로로실란, 2-노르보르닐트리클로로실란, 비닐트리클로로실란, 페닐트리클로로실란, 메틸트리브로모실란, 에틸트리브로모실란, n-프로필트리브로모실란, 이소프로필트리브로모실란, n-부틸트리브로모실란, t-부틸트리브로모실란, 시클로헥실트리브로모실란, 페네틸트리브로모실란, 2-노르보르닐트리브로모실란, 비닐트리브로모실란, 페닐트리브로모실란, 메틸트리요오드실란, 에틸트리요오드실란, n-프로필트리요오드실란, 이소프로필트리요오드실란, n-부틸트리요오드실란, t-부틸트리요오드실란, 시클로헥실트리요오드실란, 페네틸트리요오드실란, 2-노르보르닐트리요오드실란, 비닐트리요오드실란, 페닐트리요오드실란, 디메틸디클로로실란, 디에틸디클로로실란, 디-n-프로필디클로로실란, 디이소프로필디클로로실란, 디-n-부틸디클로로실란, 디-t-부틸디클로로실란, 디시클로헥실디클로로실란, 디페네틸디클로로실란, 디-2-노르보르닐디클로로실란, 디비닐디클로로실란, 디페닐디클로로실란, 디메틸디브로모실란, 디에틸디브로모실란, 디-n-프로필디브로모실란, 디이소프로필디브로모실란, 디-n-부틸디브로모실란, 디-t-부틸디브로모실란, 디시클로헥실디브로모실란, 디페네틸디브로모실란, 디-2-노르보르닐디브로모실란, 디비닐디브로모실란, 디페닐디브로모실란, 디메틸디요오드실란, 디에틸디요오드실란, 디-n-프로필디요오드실란, 디이소프로필디요오드실란, 디-n-부틸디요오드실란, 디-t-부틸디요오드실란, 디시클로헥실디요오드실란, 디페네틸디요오드실란, 디-2-노르보르닐디요오드실란, 디비닐디요오드실란, 디페닐디요오드실란, 트리메틸클로로실란, 트리에틸클로로실란, 트리-n-프로필클로로실란, 트리이소프로필클로로실란, 트리-n-부틸클로로실란, 트리-t-부틸클로로실란, 트리시클로헥실클로로실란, 트리페네틸클로로실란, 트리-2-노르보르닐클로로실란, 트리비닐클로로실란, 트리페닐클로로실란, 트리메틸브로모실란, 트리에틸브로모실란, 트리-n-프로필브로모실란, 트리이소프로필브로모실란, 트리-n-부틸브로모실란, 트리-t-부틸브로모실란, 트리시클로헥실브로모실란, 트리페네틸브로모실란, 트리-2-노르보르닐브로모실란, 트리비닐브로모실란, 트리페닐브로모실란, 트리메틸요오 드실란, 트리에틸요오드실란, 트리-n-프로필요오드실란, 트리이소프로필요오드실란, 트리-n-부틸요오드실란, 트리-t-부틸요오드실란, 트리시클로헥실요오드실란, 트리페네틸요오드실란, 트리-2-노르보르닐요오드실란, 트리비닐요오드실란, 트리페닐요오드실란 등의 규소 화합물을 들 수 있다. 이들 화합물은 1종 단독으로도 사용할 수 있고, 2종 이상을 혼합하여 사용할 수도 있다.
화합물 4는, 바람직하게는 메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-iso-프로폭시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 디메틸디메톡시실란, 디메틸디에톡시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디페닐디메톡시실란, 디페닐디에톡시실란 등이다.
이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
1.3.2. 화학식 5로 표시되는 화합물(이하, "화합물 5"라고도 함)
상기 화학식 5에서, R6, R7로 표시되는 1가의 유기기로는 상기 화학식 4와 마찬가지의 유기기를 들 수 있다.
화합물 5 중, R8이 산소 원자인 화학식 5의 화합물로는, 헥사클로로디실록산, 헥사브로모디실록산, 헥사요오드디실록산, 헥사메톡시디실록산, 헥사에톡시디실록산, 헥사페녹시디실록산, 1,1,1,3,3-펜타메톡시-3-메틸디실록산, 1,1,1,3,3-펜타에톡시-3-메틸디실록산, 1,1,1,3,3-펜타페녹시-3-메틸디실록산, 1,1,1,3,3-펜타메톡시-3-에틸디실록산, 1,1,1,3,3-펜타에톡시-3-에틸디실록산, 1,1,1,3,3-펜타페 녹시-3-에틸디실록산, 1,1,1,3,3-펜타메톡시-3-페닐디실록산, 1,1,1,3,3-펜타에톡시-3-페닐디실록산, 1,1,1,3,3-펜타페녹시-3-페닐디실록산, 1,1,3,3-테트라메톡시-1,3-디메틸디실록산, 1,1,3,3-테트라에톡시-1,3-디메틸디실록산, 1,1,3,3-테트라페녹시-1,3-디메틸디실록산, 1,1,3,3-테트라메톡시-1,3-디에틸디실록산, 1,1,3,3-테트라에톡시-1,3-디에틸디실록산, 1,1,3,3-테트라페녹시-1,3-디에틸디실록산, 1,1,3,3-테트라메톡시-1,3-디페닐디실록산, 1,1,3,3-테트라에톡시-1,3-디페닐디실록산, 1,1,3,3-테트라페녹시-1,3-디페닐디실록산, 1,1,3-트리메톡시-1,3,3-트리메틸디실록산, 1,1,3-트리에톡시-1,3,3-트리메틸디실록산, 1,1,3-트리페녹시-1,3,3-트리메틸디실록산, 1,1,3-트리메톡시-1,3,3-트리에틸디실록산, 1,1,3-트리에톡시-1,3,3-트리에틸디실록산, 1,1,3-트리페녹시-1,3,3-트리에틸디실록산, 1,1,3-트리메톡시-1,3,3-트리페닐디실록산, 1,1,3-트리에톡시-1,3,3-트리페닐디실록산, 1,1,3-트리페녹시-1,3,3-트리페닐디실록산, 1,3-디메톡시-1,1,3,3-테트라메틸디실록산, 1,3-디에톡시-1,1,3,3-테트라메틸디실록산, 1,3-디페녹시-1,1,3,3-테트라메틸디실록산, 1,3-디메톡시-1,1,3,3-테트라에틸디실록산, 1,3-디에톡시-1,1,3,3-테트라에틸디실록산, 1,3-디페녹시-1,1,3,3-테트라에틸디실록산, 1,3-디메톡시-1,1,3,3-테트라페닐디실록산, 1,3-디에톡시-1,1,3,3-테트라페닐디실록산, 1,3-디페녹시-1,1,3,3-테트라페닐디실록산 등을 들 수 있다.
이들 중에서, 헥사메톡시디실록산, 헥사에톡시디실록산, 1,1,3,3-테트라메톡시-1,3-디메틸디실록산, 1,1,3,3-테트라에톡시-1,3-디메틸디실록산, 1,1,3,3-테트라메톡시-1,3-디페닐디실록산, 1,3-디메톡시-1,1,3,3-테트라메틸디실록산, 1,3-디 에톡시-1,1,3,3-테트라메틸디실록산, 1,3-디메톡시-1,1,3,3-테트라페닐디실록산, 1,3-디에톡시-1,1,3,3-테트라페닐디실록산 등을 바람직한 예로서 들 수 있다.
또한, 화합물 5 중, d가 0인 화학식 5의 화합물로는, 헥사클로로디실란, 헥사브로모디실란, 헥사요오드디실란, 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-디에틸디실란, 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 중에서, 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, 화합물 5 중, R8이 -(CH2)e-로 표시되는 기인 화학식 5의 화합물로는, 비스(트리클로로실릴)메탄, 비스(트리브로모실릴)메탄, 비스(트리요오드실릴)메탄, 비스(트리클로로실릴)에탄, 비스(트리브로모실릴)에탄, 비스(트리요오드실릴)에탄, 비스(트리메톡시실릴)메탄, 비스(트리에톡시실릴)메탄, 비스(트리-n-프로폭시실릴)메탄, 비스(트리-i-프로폭시실릴)메탄, 비스(트리-n-부톡시실릴)메탄, 비스(트리-sec-부톡시실릴)메탄, 비스(트리-t-부톡시실릴)메탄, 1,2-비스(트리메톡시실릴)에탄, 1,2-비스(트리에톡시실릴)에탄, 1,2-비스(트리-n-프로폭시실릴)에탄, 1,2-비스(트리-i-프로폭시실릴)에탄, 1,2-비스(트리-n-1, 부톡시실릴)에탄, 1,2-비스(트리-sec-부톡시실릴)에탄, 1,1,2,2-비스(트리-t-부톡시실릴)에탄, 1-(디메톡시메틸실릴)-1-(트리메톡시실릴)메탄, 1-(디에톡시메틸실릴)-1-(트리에톡시실릴)메탄, 1-(디-n-프로폭시메틸실릴)-1-(트리-n-프로폭시실릴)메탄, 1-(디-i-프로폭시메틸실 릴)-1-(트리-i-프로폭시실릴)메탄, 1-(디-n-부톡시메틸실릴)-1-(트리-n-부톡시실릴)메탄, 1-(디-sec-부톡시메틸실릴)-1-(트리-sec-부톡시실릴)메탄, 1-(디-t-부톡시메틸실릴)-1-(트리-t-부톡시실릴)메탄, 1-(디메톡시메틸실릴)-2-(트리메톡시실릴)에탄, 1-(디에톡시메틸실릴)-2-(트리에톡시실릴)에탄, 1-(디-n-프로폭시메틸실릴)-2-(트리-n-프로폭시실릴)에탄, 1-(디-i-프로폭시메틸실릴)-2-(트리-i-프로폭시실릴)에탄, 1-(디-n-부톡시메틸실릴)-2-(트리-n-부톡시실릴)에탄, 1-(디-sec-부톡시메틸실릴)-2-(트리-sec-부톡시실릴)에탄, 1-(디-t-부톡시메틸실릴)-2-(트리-t-부톡시실릴)에탄, 비스(디메톡시메틸실릴)메탄, 비스(디에톡시메틸실릴)메탄, 비스(디-n-프로폭시메틸실릴)메탄, 비스(디-i-프로폭시메틸실릴)메탄, 비스(디-n-부톡시메틸실릴)메탄, 비스(디-sec-부톡시메틸실릴)메탄, 비스(디-t-부톡시메틸실릴)메탄, 1,2-비스(디메톡시메틸실릴)에탄, 1,2-비스(디에톡시메틸실릴)에탄, 1,2-비스(디-n-프로폭시메틸실릴)에탄, 1,2-비스(디-i-프로폭시메틸실릴)에탄, 1,2-비스(디-n-부톡시메틸실릴)에탄, 1,2-비스(디-sec-부톡시메틸실릴)에탄, 1,2-비스(디-t-부톡시메틸실릴)에탄, 1,2-비스(트리메톡시실릴)벤젠, 1,2-비스(트리에톡시실릴)벤젠, 1,2-비스(트리-n-프로폭시실릴)벤젠, 1,2-비스(트리-i-프로폭시실릴)벤젠, 1,2-비스(트리-n-부톡시실릴)벤젠, 1,2-비스(트리-sec-부톡시실릴)벤젠, 1,2-비스(트리-t-부톡시실릴)벤젠, 1,3-비스(트리메톡시실릴)벤젠, 1,3-비스(트리에톡시실릴)벤젠, 1,3-비스(트리-n-프로폭시실릴)벤젠, 1,3-비스(트리-i-프로폭시실릴)벤젠, 1,3-비스(트리-n-부톡시실릴)벤젠, 1,3-비스(트리-sec-부톡시실릴)벤젠, 1,3-비스(트리-t-부톡시실릴)벤젠, 1,4-비스(트리메톡시실릴)벤젠, 1,4-비스(트리에톡 시실릴)벤젠, 1,4-비스(트리-n-프로폭시실릴)벤젠, 1,4-비스(트리-i-프로폭시실릴)벤젠, 1,4-비스(트리-n-부톡시실릴)벤젠, 1,4-비스(트리-sec-부톡시실릴)벤젠, 1,4-비스(트리-t-부톡시실릴)벤젠 등을 들 수 있다.
이들 중에서, 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(트리에톡시실릴)벤젠, 1,4-비스(트리메톡시실릴)벤젠, 1,4-비스(트리에톡시실릴)벤젠 등을 바람직한 예로서 들 수 있다.
화합물 4, 5는 1종 또는 2종 이상을 사용할 수 있다.
또한, 상술한 중합체 (I)의 존재하에 화합물 4, 5의 군으로부터 선택된 1종 이상의 실란 화합물을 가수분해 축합시킬 때에, 화합물 4, 5의 1 몰당 0.5 몰 초과 내지 150 몰 이하의 물을 사용하는 것이 바람직하고, 0.5 몰 초과 내지 130 몰 이하의 물을 첨가하는 것이 특히 바람직하다.
본 발명의 중합체를 제조할 때에는, (A) 폴리카르보실란(중합체 (I))의 존재하에 상기 화합물 4, 5의 군으로부터 선택된 1종 이상의 실란 화합물을 가수분해 축합시킬 때에 특정한 촉매를 사용할 수 있다. 촉매로는, 알칼리 촉매, 금속 킬레 이트 촉매, 산 촉매의 군으로부터 선택되는 1종 이상을 사용할 수 있다.
알칼리 촉매로는, 예를 들면 수산화나트륨, 수산화칼륨, 수산화리튬, 피리딘, 피롤, 피페라진, 피롤리딘, 피페리딘, 피콜린, 모노에탄올아민, 디에탄올아민, 디메틸모노에탄올아민, 모노메틸디에탄올아민, 트리에탄올아민, 디아자비시클로옥탄, 디아자비시클로노난, 디아자비시클로운데센, 테트라메틸암모늄히드록시드, 테트라에틸암모늄히드록시드, 테트라프로필암모늄히드록시드, 테트라부틸암모늄히드록시드, 암모니아, 메틸아민, 에틸아민, 프로필아민, 부틸아민, 펜틸아민, 헥실아민, 펜틸아민, 옥틸아민, 노닐아민, 데실아민, N,N-디메틸아민, N,N-디에틸아민, N,N-디프로필아민, N,N-디부틸아민, 트리메틸아민, 트리에틸아민, 트리프로필아민, 트리부틸아민, 시클로헥실아민, 트리메틸이미딘, 1-아미노-3-메틸부탄, 디메틸글리신, 3-아미노-3-메틸아민 등을 들 수 있고, 아민 또는 아민염이 바람직하며, 유기 아민 또는 유기 아민염이 특히 바람직하고, 알킬아민, 테트라알킬암모늄히드록시드가 가장 바람직하다. 이들 알칼리 촉매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
금속 킬레이트 촉매로는, 예를 들면 트리에톡시?모노(아세틸아세토네이트)티탄, 트리-n-프로폭시?모노(아세틸아세토네이트)티탄, 트리-i-프로폭시?모노(아세틸아세토네이트)티탄, 트리-n-부톡시?모노(아세틸아세토네이트)티탄, 트리-sec-부톡시?모노(아세틸아세토네이트)티탄, 트리-t-부톡시?모노(아세틸아세토네이트)티탄, 디에톡시?비스(아세틸아세토네이트)티탄, 디-n-프로폭시?비스(아세틸아세토네이트)티탄, 디-i-프로폭시?비스(아세틸아세토네이트)티탄, 디-n-부톡시?비 스(아세틸아세토네이트)티탄, 디-sec-부톡시?비스(아세틸아세토네이트)티탄, 디-t-부톡시?비스(아세틸아세토네이트)티탄, 모노에톡시?트리스(아세틸아세토네이트)티탄, 모노-n-프로폭시?트리스(아세틸아세토네이트)티탄, 모노-i-프로폭시?트리스(아세틸아세토네이트)티탄, 모노-n-부톡시?트리스(아세틸아세토네이트)티탄, 모노-sec-부톡시?트리스(아세틸아세토네이트)티탄, 모노-t-부톡시?트리스(아세틸아세토네이트)티탄, 테트라키스(아세틸아세토네이트)티탄, 트리에톡시?모노(에틸아세토아세테이트)티탄, 트리-n-프로폭시?모노(에틸아세토아세테이트)티탄, 트리-i-프로폭시?모노(에틸아세토아세테이트)티탄, 트리-n-부톡시?모노(에틸아세토아세테이트)티탄, 트리-sec-부톡시?모노(에틸아세토아세테이트)티탄, 트리-t-부톡시?모노(에틸아세토아세테이트)티탄, 디에톡시?비스(에틸아세토아세테이트)티탄, 디-n-프로폭시?비스(에틸아세토아세테이트)티탄, 디-i-프로폭시?비스(에틸아세토아세테이트)티탄, 디-n-부톡시?비스(에틸아세토아세테이트)티탄, 디-sec-부톡시?비스(에틸아세토아세테이트)티탄, 디-t-부톡시?비스(에틸아세토아세테이트)티탄, 모노에톡시?트리스(에틸아세토아세테이트)티탄, 모노-n-프로폭시?트리스(에틸아세토아세테이트)티탄, 모노-i-프로폭시?트리스(에틸아세토아세테이트)티탄, 모노-n-부톡시?트리스(에틸아세토아세테이트)티탄, 모노-sec-부톡시?트리스(에틸아세토아세테이트)티탄, 모노-t-부톡시?트리스(에틸아세토아세테이트)티탄, 테트라키스(에틸아세토아세테이트)티탄, 모노(아세틸아세토네이트)트리스(에틸아세토아세테이트)티탄, 비스(아세틸아세토네이트)비스(에틸아세토아세테이트)티탄, 트리스(아세틸아세토네이트)모노(에틸아세토아세테이트)티탄 등의 티탄킬레이트 화합물;
트리에톡시?모노(아세틸아세토네이트)지르코늄, 트리-n-프로폭시?모노(아세틸아세토네이트)지르코늄, 트리-i-프로폭시?모노(아세틸아세토네이트)지르코늄, 트리-n-부톡시?모노(아세틸아세토네이트)지르코늄, 트리-sec-부톡시?모노(아세틸아세토네이트)지르코늄, 트리-t-부톡시?모노(아세틸아세토네이트)지르코늄, 디에톡시?비스(아세틸아세토네이트)지르코늄, 디-n-프로폭시?비스(아세틸아세토네이트)지르코늄, 디-i-프로폭시?비스(아세틸아세토네이트)지르코늄, 디-n-부톡시?비스(아세틸아세토네이트)지르코늄, 디-sec-부톡시?비스(아세틸아세토네이트)지르코늄, 디-t-부톡시?비스(아세틸아세토네이트)지르코늄, 모노에톡시?트리스(아세틸아세토네이트)지르코늄, 모노-n-프로폭시?트리스(아세틸아세토네이트)지르코늄, 모노-i-프로폭시?트리스(아세틸아세토네이트)지르코늄, 모노-n-부톡시?트리스(아세틸아세토네이트)지르코늄, 모노-sec-부톡시?트리스(아세틸아세토네이트)지르코늄, 모노-t-부톡시?트리스(아세틸아세토네이트)지르코늄, 테트라키스(아세틸아세토네이트)지르코늄, 트리에톡시?모노(에틸아세토아세테이트)지르코늄, 트리-n-프로폭시?모노(에틸아세토아세테이트)지르코늄, 트리-i-프로폭시?모노(에틸아세토아세테이트)지르코늄, 트리-n-부톡시?모노(에틸아세토아세테이트)지르코늄, 트리-sec-부톡시?모노(에틸아세토아세테이트)지르코늄, 트리-t-부톡시?모노(에틸아세토아세테이트)지르코늄, 디에톡시?비스(에틸아세토아세테이트)지르코늄, 디-n-프로폭시?비스(에틸아세토아세테이트)지르코늄, 디-i-프로폭시?비스(에틸아세토아세테이트)지르코늄, 디-n-부톡시?비스(에틸아세토아세테이트)지르코늄, 디-sec-부톡시?비스(에틸아세토아세테이트)지르코늄, 디-t-부톡시?비스(에틸아세토아세테 이트)지르코늄, 모노에톡시?트리스(에틸아세토아세테이트)지르코늄, 모노-n-프로폭시?트리스(에틸아세토아세테이트)지르코늄, 모노-i-프로폭시?트리스(에틸아세토아세테이트)지르코늄, 모노-n-부톡시?트리스(에틸아세토아세테이트)지르코늄, 모노-sec-부톡시?트리스(에틸아세토아세테이트)지르코늄, 모노-t-부톡시?트리스(에틸아세토아세테이트)지르코늄, 테트라키스(에틸아세토아세테이트)지르코늄, 모노(아세틸아세토네이트)트리스(에틸아세토아세테이트)지르코늄, 비스(아세틸아세토네이트)비스(에틸아세토아세테이트)지르코늄, 트리스(아세틸아세토네이트)모노(에틸아세토아세테이트)지르코늄 등의 지르코늄킬레이트 화합물;
트리스(아세틸아세토네이트)알루미늄, 트리스(에틸아세토아세테이트)알루미늄 등의 알루미늄킬레이트 화합물;
등을 들 수 있고, 바람직하게는 티탄 또는 알루미늄의 킬레이트 화합물, 특히 바람직하게는 티탄의 킬레이트 화합물을 들 수 있다. 이들 금속 킬레이트 촉매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
산 촉매로는, 예를 들면 염산, 질산, 황산, 불화수소산, 인산, 붕산 등의 무기산;
아세트산, 프로피온산, 부탄산, 펜탄산, 헥산산, 헵탄산, 옥탄산, 노난산, 데칸산, 옥살산, 말레산, 메틸말론산, 아디프산, 세박산, 갈산, 부티르산, 메리트산, 아라키돈산, 시킴산, 2-에틸헥산산, 올레산, 스테아르산, 리놀레산, 리놀렌산, 살리실산, 벤조산, p-아미노벤조산, p-톨루엔술폰산, 벤젠술폰산, 모노클로로아세트산, 디클로로아세트산, 트리클로로아세트산, 트리플루오로아세트산, 포름산, 옥 살산, 말론산, 술폰산, 프탈산, 푸마르산, 시트르산, 타르타르산, 숙신산, 푸마르산, 이타콘산, 메사콘산, 시트라콘산, 말산, 글루타르산의 가수분해물, 말레산 무수물의 가수분해물, 프탈산 무수물의 가수분해물 등의 유기산을 들 수 있고, 유기 카르복실산을 보다 바람직한 예로서 들 수 있다. 이들 산 촉매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
상기 촉매의 사용량은, 화합물 4, 5 중 X, Y, Z로 표시되는 기의 총량 1 몰에 대하여, 통상 0.00001 내지 10 몰, 바람직하게는 0.00005 내지 5 몰이다. 촉매의 사용량이 상기 범위 내이면, 반응 중 중합체의 석출이나 겔화의 우려가 적다. 또한, 본 발명에서 화합물 4, 5를 가수분해할 때의 온도는 통상 0 내지 100 ℃, 바람직하게는 15 내지 80 ℃이다.
본 발명에서, "완전 가수분해 축합물"이란, (A) 폴리카르보실란 및 화합물 4, 5 중 가수분해성기가 100 % 가수분해하여 SiOH기가 되고, 추가로 완전히 축합되어 실록산 구조가 된 것을 말한다.
또한, 축합물로는, 얻어지는 조성물의 저장 안정성이 보다 우수하기 때문에, (A) 폴리카르보실란과 화합물 4의 가수분해 축합물이 바람직하다. 본 발명에서, (A) 폴리카르보실란에 대한 화합물 4, 5의 사용량은 (A) 폴리카르보실란 100 중량부에 대하여, 화합물 4, 5의 총량 성분이 500 내지 4000 중량부, 보다 바람직하게는 1000 내지 3000 중량부이다.
본 발명에서 중합체의 폴리스티렌 환산 중량 평균 분자량은, 통상 1,500 내지 500,000인 것이 바람직하고, 2,000 내지 200,000인 것이 보다 바람직하며, 2,000 내지 100,000인 것이 더욱 바람직하다. 중합체의 폴리스티렌 환산 중량 평균 분자량이 1,500 미만이면 목적으로 하는 비유전율이 얻어지지 않는 경우가 있고, 한편 500,000을 초과하면 도막의 면내 균일성이 떨어지는 경우가 있다.
2. 절연막 형성용 조성물
본 발명의 절연막 형성용 조성물(이하, "막 형성용 조성물"이라 함)에는, 본 발명의 중합체에 추가로 유기 중합체, 계면활성제 등의 성분을 첨가할 수도 있다.
유기 중합체로는, 예를 들면 (메트)아크릴계 중합체, 폴리알킬렌옥시드 구조를 갖는 화합물 등을 들 수 있다.
폴리알킬렌옥시드 구조를 갖는 화합물로는, 폴리메틸렌옥시드 구조, 폴리에틸렌옥시드 구조, 폴리프로필렌옥시드 구조, 폴리테트라메틸렌옥시드 구조, 폴리부틸렌옥시드 구조 등을 들 수 있다.
구체적으로는, 폴리옥시메틸렌알킬에테르, 폴리옥시에틸렌알킬에테르, 폴리옥시에틸렌알킬페닐에테르, 폴리옥시에틸렌스테롤에테르, 폴리옥시에틸렌라놀린 유도체, 알킬페놀포르말린 축합물의 산화에틸렌 유도체, 폴리옥시에틸렌폴리옥시프로필렌 블럭 공중합체, 폴리옥시에틸렌폴리옥시프로필렌알킬에테르 등의 에테르형 화합물, 폴리옥시에틸렌글리세린 지방산 에스테르, 폴리옥시에틸렌소르비탄 지방산 에스테르, 폴리옥시에틸렌소르비톨 지방산 에스테르, 폴리옥시에틸렌 지방산 알칸올아미드황산염 등의 에테르에스테르형 화합물, 폴리에틸렌글리콜 지방산 에스테르, 에틸렌글리콜 지방산 에스테르, 지방산 모노글리세라이드, 폴리글리세린 지방산 에스테르, 소르비탄 지방산 에스테르, 프로필렌글리콜 지방산 에스테르, 수크로 스 지방산 에스테르 등의 에테르에스테르형 화합물 등을 들 수 있다.
폴리옥시에틸렌폴리옥시프로필렌 블럭 공중합체로는 하기와 같은 블럭 구조를 갖는 화합물을 들 수 있다.
-(X')j-(Y')k-
-(X')j-(Y')k-(X')l-
식 중, X'은-CH2CH2O-로 표시되는 기를 나타내고, Y'은 -CH2CH(CH3)O-으로 표시되는 기를 나타내고, j는 1 내지 90의 수를 나타내고, k는 10 내지 99의 수를 나타내고, l은 0 내지 90의 수를 나타낸다.
이들 중에서, 폴리옥시에틸렌알킬에테르, 폴리옥시에틸렌폴리옥시프로필렌 블럭 공중합체, 폴리옥시에틸렌폴리옥시프로필렌알킬에테르, 폴리옥시에틸렌글리세린 지방산 에스테르, 폴리옥시에틸렌소르비탄 지방산 에스테르, 폴리옥시에틸렌소르비톨 지방산 에스테르 등의 에테르형 화합물을 보다 바람직한 예로서 들 수 있다. 이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
계면활성제로는, 예를 들면 비이온계 계면활성제, 음이온계 계면활성제, 양이온계 계면활성제, 양쪽성 계면활성제 등을 들 수 있고, 또는 불소계 계면활성제, 실리콘계 계면활성제, 폴리알킬렌옥시드계 계면활성제, 폴리(메트)아크릴레이트계 계면활성제 등을 들 수 있으며, 바람직하게는 불소계 계면활성제, 실리콘계 계면활성제를 들 수 있다.
불소계 계면활성제로는, 예를 들면 1,1,2,2-테트라플루오로옥틸(1,1,2,2-테 트라플루오로프로필)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-카르복시메틸렌암모늄베타인, 퍼플루오로알킬술폰아미드프로필트리메틸암모늄염, 퍼플루오로알킬-N-에틸술포닐글리신염, 인산비스(N-퍼플루오로옥틸술포닐-N-에틸아미노에틸), 모노퍼플루오로알킬에틸인산에스테르 등의 말단, 주쇄 및 측쇄 중 적어도 하나의 부위에 플루오로알킬 또는 플루오로알킬렌기를 갖는 화합물로 이루어지는 불소계 계면활성제를 들 수 있다.
또한, 시판품으로는 메가팩 F142D, 동 F172, 동 F173, 동 F183(이상, 다이닛본 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,서플론 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 시판되고 있는 불소계 계면활성제를 들 수 있다. 이들 중에서도, 상기 메가팩 F172, BM-1000, BM-1100, NBX-15가 특히 바람직하다.
실리콘계 계면활성제로는, 예를 들면 SH7PA, SH21PA, SH30PA, ST94PA(모두 도레이?다우코닝?실리콘(주) 제조) 등을 사용할 수 있다. 이들 중에서도, 상기 SH28PA, SH30PA가 특히 바람직하다.
계면활성제의 사용량은, 중합체(완전 가수분해 축합물)에 대하여 통상 0.0001 내지 10 중량부이다. 이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
본 발명의 막 형성용 조성물로는 본 발명의 중합체 (가수분해 축합물) 및 필요에 따라서 추가로 첨가제를 유기 용제에 용해 또는 분산시킬 수 있다.
이 때 사용할 수 있는 유기 용제로는, 알코올계 용매, 케톤계 용매, 아미드계 용매, 에스테르계 용매 및 비양성자계 용매의 군으로부터 선택된 1종 이상을 들 수 있다.
여기서 알코올계 용매로는, 메탄올, 에탄올, n-프로판올, i-프로판올, n-부탄올, i-부탄올, sec-부탄올, t-부탄올, n-펜탄올, i-펜탄올, 2-메틸부탄올, sec-펜탄올, t-펜탄올, 3-메톡시부탄올, n-헥산올, 2-부틸펜탄올, 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 알코올 계 용매;
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 또는 2종 이상을 동시에 사용할 수도 있다.
케톤계 용매로는, 아세톤, 메틸에틸케톤, 메틸-n-프로필케톤, 메틸-n-부틸케톤, 디에틸케톤, 메틸-i-부틸케톤, 메틸-n-펜틸케톤, 에틸-n-부틸케톤, 메틸-n-헥실케톤, 디-i-부틸케톤, 트리메틸노나논, 시클로헥사논, 2-헥사논, 메틸시클로헥사논, 2,4-펜탄디온, 아세토닐아세톤, 아세토페논, 펜촌 등 이외에, 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 또는 2종 이상을 동시에 사용할 수도 있다.
아미드계 용매로는, 포름아미드, N-메틸포름아미드, N,N-디메틸포름아미드, N-에틸포름아미드, N,N-디에틸포름아미드, 아세트아미드, N-부틸아세트아미드, 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 또는 2종 이상을 동시에 사용할 수도 있다.
에스테르계 용매로는, 디에틸카르보네이트, 탄산에틸렌, 탄산프로필렌, 탄산디에틸, 아세트산메틸, 아세트산에틸, γ-부티로락톤, γ-발레로락톤, 아세트산 n-프로필, 아세트산 i-프로필, 아세트산 n-부틸, 아세트산 i-부틸, 아세트산 sec-부틸, 아세트산 n-펜틸, 아세트산 sec-펜틸, 아세트산 3-메톡시부틸, 아세트산메틸펜틸, 아세트산 2-에틸부틸, 아세트산 2-에틸헥실, 아세트산벤질, 아세트산시클로헥실, 아세트산메틸시클로헥실, 아세트산 n-노닐, 아세토아세트산메틸, 아세토아세트산에틸, 아세트산에틸렌글리콜 모노메틸에테르, 아세트산에틸렌글리콜 모노에틸에테르, 아세트산디에틸렌글리콜 모노메틸에테르, 아세트산디에틸렌글리콜 모노에틸에테르, 아세트산디에틸렌글리콜 모노-n-부틸에테르, 아세트산프로필렌글리콜 모노메틸에테르, 아세트산프로필렌글리콜 모노에틸에테르, 아세트산프로필렌글리콜 모노프로필에테르, 아세트산프로필렌글리콜 모노부틸에테르, 아세트산디프로필렌글리콜 모노메틸에테르, 아세트산디프로필렌글리콜 모노에틸에테르, 디아세트산글리콜, 아세트산메톡시트리글리콜, 프로피온산에틸, 프로피온산 n-부틸, 프로피온산 i-아밀, 옥살산디에틸, 옥살산디-n-부틸, 락트산메틸, 락트산에틸, 락트산 n-부틸, 락 트산 n-아밀, 말론산디에틸, 프탈산디메틸, 프탈산디에틸 등을 들 수 있다. 이들에스테르계 용매는 1종 또는 2종 이상을 동시에 사용할 수도 있다.
비양성자계 용매로는, 아세토니트릴, 디메틸술폭시드, N,N,N',N'-테트라에틸술파미드, 헥사메틸인산트리아미드, N-메틸모르폴론, 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 또는 2종 이상을 동시에 사용할 수도 있다.
이와 같이 하여 얻어지는 본 발명의 막 형성용 조성물의 전체 고형분 농도는, 바람직하게는 2 내지 30 중량%이고, 사용 목적에 따라서 적절하게 조정된다. 막 형성용 조성물의 전체 고형분 농도가 2 내지 30 중량%이면, 도막의 막 두께가 적당한 범위가 되고, 보존 안정성도 보다 우수하다. 또한, 이 전체 고형분 농도의 조정은 필요하면 농축 및 상기 유기 용제에 의한 희석에 의해서 행해진다.
3. 절연막
본 발명의 절연막은 상기 막 형성용 조성물을 도포하여 도막을 형성한 후, 도막을 가열함으로써 얻어진다.
본 발명의 막 형성용 조성물을 실리콘 웨이퍼, SiO2 웨이퍼, SiN 웨이퍼 등의 기재에 도포할 때에는, 스핀 코팅, 침지법, 롤 코팅법, 분무법 등의 도장 수단이 사용된다.
이 때의 막 두께는, 건조 막 두께로서 1회 도장하여 두께 0.05 내지 2.5 ㎛ 정도, 2회 도장하여 두께 0.1 내지 5.0 ㎛ 정도의 도막을 형성할 수 있다. 그 후, 상온에서 건조하거나, 80 내지 600 ℃ 정도의 온도에서 통상 5 내지 240 분 정도 가열하여 건조함으로써, 유리질 또는 거대 분자의 도막을 형성할 수 있다.
이 때의 가열 방법으로는, 핫 플레이트, 오븐, 퍼니스 등을 사용할 수 있고, 가열 분위기로는, 대기하, 질소 분위기, 아르곤 분위기, 진공하, 산소 농도를 조절한 감압하 등에서 행할 수 있다.
또한, 상기 도막의 경화 속도를 제어하기 위해서, 필요에 따라서 단계적으로 가열하거나, 질소, 공기, 산소, 감압 등의 분위기를 선택할 수 있다.
또한, 본 발명에서는 막 형성용 조성물을 기판에 도포하고, 고에너지선 조사하에서 30 내지 450 ℃로 가열할 수도 있다.
이와 같이 하여 얻어지는 본 발명의 실리카계의 절연막은, 막 밀도가 통상 0.35 내지 1.2 g/㎤, 바람직하게는 0.4 내지 1.1 g/㎤, 더욱 바람직하게는 O.5 내지 1.0 g/㎤이다. 막 밀도가 0.35 g/㎤ 미만이면, 도막의 기계적 강도가 저하되고, 한편 1.2 g/㎤를 초과하면 저 비유전율이 얻어지지 않는다. 또한, 본 발명의 절연막의 비유전율은 통상 3.2 내지 1.2, 바람직하게는 3.0 내지 1.5, 더욱 바람직하게는 2.7 내지 1.8이다.
본 발명의 절연막은 막 구조 중에 규소-탄소 결합을 많이 갖는다는 특징을 갖는다. 이 특징에 의해 절연성, 도포막의 균일성, 유전율 특성, 도막의 탄성률, 도막의 밀착성이 우수하다.
본 발명의 절연막은 저 비유전율이며 균열 내성이나 기계적 강도나 밀착성이 우수하기 때문에, LSI, 시스템 LSI, DRAM, SDRAM, RDRAM, D-RDRAM 등의 반도체 소자용 층간 절연막이나 에칭 스토퍼막, 반도체 소자의 표면 코팅막 등의 보호막, 다층 레지스트를 사용한 반도체 제조 공정의 중간층, 다층 배선 기판의 층간 절연막, 액정 표시 소자용 보호막이나 절연막 등의 용도에 유용하다.
4. 실시예
이하, 본 발명을 실시예를 들어 더욱 구체적으로 설명한다. 본 발명은 이하의 실시예로 한정되는 것은 아니다. 또한, 실시예 및 비교예 중 "부" 및 "%"는 특기하지 않는 한, 각각 중량부 및 중량%인 것을 나타내고 있다.
4.1. 평가 방법
각종 평가는 다음과 같이 행하였다.
4.1.1. 중합체의 중량 평균 분자량(Mw)
하기 조건에 의한 겔 투과 크로마토그래피(GPC)법에 의해 측정하였다.
시료: 테트라히드로푸란을 용매로서 사용하고, 중합체(가수분해 축합물) 1 g을 100 cc의 테트라히드로푸란에 용해시켜 제조하였다.
표준 폴리스티렌: 미국 프레셔 케미컬사 제조의 표준 폴리스티렌을 사용하였다.
장치: 미국 워터즈사 제조의 고온 고속 겔 침투 크로마토그램(모델 150-CALC/GPC)
칼럼: 쇼와 덴꼬(주) 제조의 쇼덱스(SHODEX) A-80M(길이 50 cm)
측정 온도: 40 ℃
유속: 1 cc/분
4.1.2. 비유전율
얻어진 절연막에 대하여 증착법에 의해 알루미늄 전극 패턴을 형성시키고, 비유전율 측정용 샘플을 제조하였다. 상기 샘플을 주파수 100 kHz의 주파수에서, 요꼬가와?휴렛팩커드(주) 제조의 HP16451B 전극 및 HP4284A 플래시죤 LCR 미터를 사용하여, CV법에 의해 실온에서의 해당 도막의 비유전율을 측정하였다.
4.1.3. 기계적 강도(탄성률?경도)
얻어진 절연막에 대해서, 나노인덴터 XP(나노인스트루먼트사 제조)를 이용하여, 연속 강성 측정법에 의해 탄성률 및 경도를 측정하였다.
4.1.4. 밀착성
얻어진 절연막 상에 스퍼터법으로 SiO2막을 400 nm 형성하고, 이것을 적당한 크기로 절단한 후, 그 웨이퍼 한쪽 상에 동일한 크기의 블랭크 실리콘 웨이퍼를 에폭시 수지를 사용하여 접착하고, 오븐 중 135 ℃에서 2 시간 동안 가열하였다. 이것을, 다이싱머신으로 작은 조각으로 절단하고, 각각에 대하여 4점 굴곡 밀착력 측정법에 의한 박리 시험을 행하였다. 결과는 이하와 같이 나타낸다.
A: 밀착 에너지가 3.0 J마다 ㎡ 이상인 것
B: 밀착 에너지가 3.0 J마다 ㎡ 미만인 것
4.1.5. 막의 상분리 유무 확인
절연막의 단면을 집속 이온빔법으로 관찰용으로 가공하고, TEM을 이용하여 18000배로 외관을 조사하였다. 판단 결과를 이하와 같이 나타낸다.
A: 단면의 형상 관찰에서는, 균일한 도막이 얻어지고 있다.
B: 도막에 해도(海島)상의 도메인 상분리가 확인된다.
4.2. (A) 폴리카르보실란의 합성예
4.2.1. 합성예 1
온도계, 냉각 콘덴서, 적하 로트 및 교반 장치를 장착한 내용량이 3 ℓ인 4구 플라스크 내를 아르곤 가스로 치환한 후, 건조한 테트라히드로푸란 1 ℓ와 금속 마그네슘 60.8 g을 넣고, 아르곤 가스로 버블링하였다. 이것에, 20 ℃에서 교반하면서, 디클로로디에톡시실란 189.1 g과 디브로모메탄 173.8 g의 혼합물을 적하 로트로부터 천천히 첨가하였다.
적하 종료 후, 45 ℃에서 추가로 24 시간 동안 교반을 계속하였다. 냉각한 후, 이 반응액으로부터 여과에 의해 생성된 마그네슘염을 제거하였다. 계속해서, 여과액을 감압 가열 조작함으로써, 테트라히드로푸란을 여과액으로부터 제거하고, 점조한 갈색 액체 중합체 119 g을 얻었다. 이와 같이 하여 얻어진 중합체 (1)의 중량 평균 분자량은 1,200이었다.
4.2.2. 합성예 2
온도계, 냉각 콘덴서, 적하 로트 및 교반 장치를 장착한 내용량이 4 ℓ인 4구 플라스크 내를 아르곤 가스로 치환한 후, 건조한 테트라히드로푸란 1.5 ℓ 및 금속 마그네슘 71 g을 넣고, 아르곤 가스로 버블링하였다. 이것에, 0 ℃에서 교반하면서, 클로로메틸트리에톡시실란 500 g을 적하 로트로부터 천천히 첨가하였다.
적하 종료 후, 0 ℃에서 추가로 12 시간 동안 교반을 계속하였다. 이 반응액에 헥산을 첨가한 후 셀라이트로 여과하고, 진공 오븐으로 유기 용매를 완전히 제거하고, 갈색 액체의 중합체 (2) 414 g을 얻었다.
이와 같이 하여 얻어진 중합체 (2)의 중량 평균 분자량은 420이었다.
4.2.3. 합성예 3
온도계, 냉각 콘덴서, 적하 로트 및 교반 장치를 장착한 내용량이 3 ℓ인 4구 플라스크 내를 아르곤 가스로 치환한 후, 건조한 테트라히드로푸란 1 ℓ 및 금속 마그네슘 60.8 g을 넣고, 아르곤 가스로 버블링하였다. 이것에, 20 ℃에서 교반하면서, 메틸트리클로로실란 74.8 g, 디브로모메탄 86.9 g 및 클로로메틸트리클로로실란 92.0 g의 혼합물을 적하 로트로부터 천천히 첨가하였다.
적하 종료 후, 45 ℃에서 추가로 24 시간 동안 교반을 계속하였다. 냉각한 후, 이 반응액으로부터 여과에 의해 생성된 마그네슘염을 제거하였다. 계속해서, 여과액을 감압 가열 조작함으로써, 테트라히드로푸란을 여과액으로부터 제거하고, 갈색 액체 중합체 46 g을 얻었다.
이와 같이 하여 얻어진 중합체 (3)의 중량 평균 분자량은 860이었다.
4.3. 실시예, 비교예
4.3.1. 실시예 1
석영제 분리형 플라스크 중에서, 합성예 1에서 얻은 중합체 (1) 5.1 g, 메틸 트리메톡시실란 50 g 및 트리에틸아민 0.0031 g을 메탄올 250 g에 용해시킨 후, 쓰리원모터(three-one motor)로 교반시키고, 용액 온도를 55 ℃로 안정시켰다. 이어서, 이온 교환수 50.4 g 및 프로필렌글리콜 모노에틸에테르 203 g의 혼합 용액을 1 시간에 걸쳐 용액에 첨가하였다.
그 후, 55 ℃에서 4 시간 동안 반응시킨 후, 아세트산의 10 % 프로필렌글리콜 모노프로필에테르 용액 10 g을 첨가하고, 추가로 30 분간 반응시킨 후, 반응액을 실온으로 냉각하였다. 50 ℃에서, 반응액으로부터 메탄올 및 물을 포함하는 용액 298 g을 증발시켜 제거하고, 반응액 A를 얻었다. 이와 같이 하여 얻어진 본 발명의 중합체(이하, "축합물"이라 함)의 중량 평균 분자량은 27,000이었다.
4.3.2. 실시예 2
석영제 분리형 플라스크 중에서, 합성예 1에서 얻은 중합체 (1) 5.0 g, 테트라에톡시실란 49 g 및 트리에틸아민 0.0030 g을 메탄올 253 g에 용해시킨 후, 쓰리원모터로 교반시키고, 용액 온도를 55 ℃로 안정시켰다. 이어서, 이온 교환수50.2 g 및 프로필렌글리콜 모노에틸에테르 200 g의 혼합 용액을 1 시간에 걸쳐 용액에 첨가하였다.
그 후, 55 ℃에서 4 시간 동안 반응시킨 후, 아세트산의 10 % 프로필렌글리콜 모노프로필에테르 용액 10 g을 첨가하고, 추가로 30 분간 반응킨 후, 반응액을 실온으로 냉각하였다. 50 ℃에서 반응액으로부터 메탄올 및 물을 포함하는 용액299 g을 증발시켜 제거하고, 반응액 B를 얻었다. 이와 같이 하여 얻어진 축합물의 중량 평균 분자량은 31,000이었다.
4.3.3. 실시예 3
석영제 분리형 플라스크 중에서, 합성예 1에서 얻은 중합체 (1) 5.1 g, 메틸트리메톡시실란 50 g 및 메탄올 248 g을 프로필렌글리콜 모노프로필에테르 용액 201 g에 용해시킨 후, 쓰리원모터로 교반시키고, 용액 온도를 55 ℃로 안정시켰다. 이어서, 숙신산 0.12 g을 용해시킨 이온 교환수 24 g을 1 시간에 걸쳐 용액에 첨가하였다. 그 후, 50 ℃에서 3 시간 동안 반응시킨 후, 반응액을 실온으로 냉각하였다. 50 ℃에서 반응액으로부터 물을 포함하는 용액 272 g을 증발시켜 제거하고, 반응액 C를 얻었다. 이와 같이 하여 얻어진 축합물의 중량 평균 분자량은 3,200이었다.
4.3.4. 실시예 4
실시예 1에서 얻어진 반응액 A를 0.2 ㎛ 공경의 테플론(등록상표)제 필터로 여과를 행하여, 본 발명의 막 형성용 조성물을 얻었다.
얻어진 조성물을 스핀 코팅법으로 실리콘 웨이퍼 상에 도포한 후, 핫 플레이트 상에서 90 ℃에서 3 분간, 이어서 질소 분위기하 200 ℃에서 3 분간 기판을 건조하고, 추가로 400 ℃의 질소 분위기하 핫 플레이트에서 60 분간 기판을 소성하였다. 소성 후에 얻어진 절연막(이하, "실리카계 막"이라 함)을 5.1.의 평가 방법과 마찬가지로 평가하였다. 평가 결과를 하기 표 1에 나타낸다.
4.3.5. 실시예 5, 6
실시예 4에서 반응액 A를 사용하는 대신에, 각각 반응액 B, C를 사용한 것 이외에는, 실시예 4와 마찬가지로 실리카계 막을 형성하고, 그 평가를 행하였다. 평가 결과를 표 1에 나타낸다.
4.3.6. 실시예 7
석영제 분리형 플라스크 중에서, 합성예 3에서 얻은 중합체 (3) 6.2 g 및 톨루엔 50 g에 용해시켰다. 계속해서, 메틸트리메톡시실란 50 g을 천천히 적하하였다. 이어서, 숙신산 0.12 g, 이온 교환수 24 g, 테트라히드로푸란 용액 201 g의 혼합 용액을 1 시간에 걸쳐 적하한 후, 50 ℃에서 3 시간 동안 반응시킨 후, 반응액을 실온으로 냉각하였다. 계속해서, 용액 중에 디에틸에테르를 300 g 추가한 후, 초순수로 pH가 중성이 될 때까지 수세를 행하였다. 유기 상에 프로필렌글리콜 모노에틸에테르 300 g을 첨가한 후, 고형분 농도가 20 %가 될 때까지 농축을 행하고, 반응액 D를 얻었다. 이와 같이 하여 얻어진 축합물의 중량 평균 분자량은 2,640이었다. 이 반응액 D를 사용한 것 이외에는, 실시예 4와 동일하게 하여 실리카계 막을 형성하고, 그 평가를 행하였다. 평가 결과를 표 1에 나타낸다.
4.3.7. 비교예 1
합성예 1에서 얻어진 중합체 (1) 1.0 g을 프로필렌글리콜 모노프로필에테르 4.0 g에서 용해시켜 얻어진 반응액 E를 도포 용액으로서 사용한 것 이외에는, 실시예 4와 동일하게 하여 실리카계 막을 형성하고, 그 평가를 행하였다. 평가 결과를 표 1에 나타낸다.
4.3.8. 비교예 2
석영제 분리형 플라스크에 증류 에탄올 430 g, 이온 교환수 211 g 및 25 %의 테트라메틸암모늄히드록시드 수용액 15.2 g을 넣고, 균일하게 교반하였다. 이 용액에 메틸트리메톡시실란 40.0 g 및 테트라에톡시실란 61.1 g의 혼합물을 첨가하였다. 이 용액을 60 ℃로 유지한 상태에서 2 시간 동안 반응시켰다. 이 용액에 프로필렌글리콜 모노프로필에테르 300 g을 첨가한 후, 50 ℃의 증발기를 이용하여 용액을 20 %(완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후, 말레산의 10 % 프로필렌글리콜 모노프로필에테르 용액 20 g을 첨가하여 반응액 F를 얻었다. 이 반응액 F를 사용한 것 이외에는, 실시예 4와 동일하게 하여 실리카계 막을 형성하고, 그 평가를 행하였다. 평가 결과를 표 1에 나타낸다.
4.3.9. 비교예 3
화학식 [Si(CH3)(H)-CH2]-로 표시되는 반복 단위로 이루어지는 중량 평균 분자량 20,000의 폴리카르보실란의 프로필렌글리콜 모노프로필에테르 25 % 용액(이하, "반응액 I"라 함)과 비교예 2의 반응액 F를 I:F=2:8의 중량비로 혼합한 액을 제조하여 반응액 G를 얻었다. 이 반응액 G를 사용한 것 이외에는, 실시예 4와 동일하게 하여 실리카계 막을 형성하고, 그 평가를 행하였다. 평가 결과를 표 1에 함께 나타낸다.
4.3.10. 비교예 4
합성예 2에서 얻어진 중합체 (2) 9 g, 메틸트리메톡시실란 30.0 g 및 테트라메톡시실란 3.4 g을 테트라히드로푸란 60 ㎖에 혼합하고, 이 혼합액을 0 ℃로 한 후, 0.01 N의 질산 37 ㎖를 서서히 첨가하여 30 분간 반응시켰다. 이어서, 70 ℃까지 승온하여 16 시간 동안 환류시키면서 반응시켰다. 이어서, 반응액을 방냉한 후, 디에틸에테르 250 ㎖로 희석하고 나서, pH가 중성이 될 때까지 증류수로 3 내지 4회 세정하였다. 이 용액에 프로필렌글리콜 모노프로필에테르 200 g을 첨가한 후, 50 ℃의 증발기를 이용하여 용액을 20 %(완전 가수분해 축합물 환산)가 될 때까지 농축하고, 그 후, 말레산의 10 % 프로필렌글리콜 모노프로필에테르 용액 20 g을 첨가하여 반응액 H를 얻었다. 이 반응액 H를 사용한 것 이외에는, 실시예 4와 동일하게 하여 실리카계 막을 형성하고, 그 평가를 행하였다. 평가 결과를 표 1에 나타낸다.
Claims (6)
- (A) 폴리카르보실란의 존재하에 (B) 가수분해성기 함유 실란 단량체를 가수분해 축합하는 것을 포함하고,상기 (A) 폴리카르보실란은, (a) 하기 화학식 1로 표시되는 화합물과, (b) 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물의 군으로부터 선택된 1종 이상을 유기 용매 중에서 알칼리 금속 및 알칼리 토금속 중 하나 이상의 존재하에서 반응시켜 얻어지는 중합체 (I)이며,상기 (B) 가수분해성기 함유 실란 단량체가 하기 화학식 4로 표시되는 화합물 및 하기 화학식 5로 표시되는 화합물의 군으로부터 선택된 1종 이상의 실란 화합물인,중합체의 제조 방법.<화학식 1>R1 kCX4-k<화학식 2>R2 kSiY4-k<화학식 3>R3 mY3-mSiCR4 nX3-n(상기 식 중, R1 내지 R4는 동일하거나 상이하고, 각각 탄소수가 1 내지 10인 직쇄상 또는 분지쇄상 지방족기, 탄소수가 3 내지 20인 지환식기, 탄소수가 6 내지 20인 아릴기, 탄소수가 6 내지 20인 아랄킬기 또는 수소 원자를 나타내며, X는 할로겐 원자를 나타내고, Y는 할로겐 원자 또는 알콕시기(-OR)(여기서, R은 알킬기 또는 아릴기임)를 나타내며, k는 0 내지 3의 정수를 나타내고, m 및 n은 동일하거나 상이하며, 0 내지 2의 정수를 나타낸다)<화학식 4>R5 aSiX4-a(화학식 4 중, R5는 수소 원자, 불소 원자, 알킬기, 아릴기, 알릴기, 글리시딜기 또는 비닐기를 나타내고, X는 할로겐 원자 또는 알콕시기(-OR)(여기서, R은 알킬기, 아릴기, 알릴기, 글리시딜기 또는 비닐기임)를 나타내며, a는 0 내지 3의 정수를 나타낸다.)<화학식 5>R6 bY3-bSi-(R8)d-SiZ3-cR7 c(화학식 5 중, R6, R7은 동일하거나 상이하고, 각각 알킬기, 아릴기, 알릴기, 글리시딜기 또는 비닐기를 나타내며, b 및 c는 동일하거나 상이하고, 0 내지 2의 정수를 나타내며, R8은 산소 원자, 페닐렌기 또는 -(CH2)e-로 표시되는 기(여기서, e는 1 내지 6의 정수임)를 나타내고, Y 및 Z는 동일하거나 상이하며, 할로겐 원자 또는 알콕시기(-OR)(여기서, R은 알킬기, 아릴기, 알릴기, 글리시딜기 또는 비닐기임)를 나타내고, d는 0 또는 1을 나타낸다)
- 제1항에 기재된 중합체의 제조 방법에 의해서 얻어지는 중합체.
- 제2항에 기재된 중합체 및 유기 용제를 함유하는 절연막 형성용 조성물.
- 제3항에 기재된 절연막 형성용 조성물을 기판에 도포하고, 30 내지 450 ℃로 가열하는 것을 포함하는 절연막의 제조 방법.
- 제4항에 기재된 절연막의 제조 방법에 의해 얻어지는 실리카계 절연막.
- 삭제
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- 2005-01-14 WO PCT/JP2005/000373 patent/WO2005068539A1/ja active Application Filing
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US20070021580A1 (en) | 2007-01-25 |
WO2005068538A1 (ja) | 2005-07-28 |
US20070015892A1 (en) | 2007-01-18 |
EP1705207A4 (en) | 2009-06-24 |
EP1705207B1 (en) | 2012-10-24 |
US7528207B2 (en) | 2009-05-05 |
EP1705207A1 (en) | 2006-09-27 |
TWI265172B (en) | 2006-11-01 |
KR20060123548A (ko) | 2006-12-01 |
EP1705206A4 (en) | 2009-06-24 |
TW200538490A (en) | 2005-12-01 |
KR20060123549A (ko) | 2006-12-01 |
JP5013045B2 (ja) | 2012-08-29 |
TW200536621A (en) | 2005-11-16 |
JPWO2005068538A1 (ja) | 2007-12-27 |
TWI292349B (ko) | 2008-01-11 |
JPWO2005068539A1 (ja) | 2007-12-27 |
JP5110243B2 (ja) | 2012-12-26 |
EP1705206A1 (en) | 2006-09-27 |
WO2005068539A1 (ja) | 2005-07-28 |
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