KR101153634B1 - 막 형성용 조성물 및 그의 제조 방법 - Google Patents
막 형성용 조성물 및 그의 제조 방법 Download PDFInfo
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- KR101153634B1 KR101153634B1 KR1020040097442A KR20040097442A KR101153634B1 KR 101153634 B1 KR101153634 B1 KR 101153634B1 KR 1020040097442 A KR1020040097442 A KR 1020040097442A KR 20040097442 A KR20040097442 A KR 20040097442A KR 101153634 B1 KR101153634 B1 KR 101153634B1
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- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- -1 silane compound Chemical class 0.000 claims abstract description 58
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 229910000077 silane Inorganic materials 0.000 claims abstract description 24
- 125000000962 organic group Chemical group 0.000 claims abstract description 23
- 239000003513 alkali Substances 0.000 claims abstract description 22
- 239000011248 coating agent Substances 0.000 claims abstract description 17
- 238000000576 coating method Methods 0.000 claims abstract description 17
- 230000007062 hydrolysis Effects 0.000 claims abstract description 15
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 8
- 150000004756 silanes Chemical class 0.000 claims abstract description 7
- 239000007859 condensation product Substances 0.000 claims abstract description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 84
- 239000000377 silicon dioxide Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
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- 150000003997 cyclic ketones Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 13
- 239000001301 oxygen Substances 0.000 abstract description 13
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- 238000009833 condensation Methods 0.000 abstract description 7
- 230000005494 condensation Effects 0.000 abstract description 7
- 239000010408 film Substances 0.000 description 135
- 150000001875 compounds Chemical class 0.000 description 18
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
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- 229940125904 compound 1 Drugs 0.000 description 11
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 239000011229 interlayer Substances 0.000 description 8
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000006482 condensation reaction Methods 0.000 description 7
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000012299 nitrogen atmosphere 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
- 229910021642 ultra pure water Inorganic materials 0.000 description 6
- 239000012498 ultrapure water Substances 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 5
- 229940087646 methanolamine Drugs 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000003002 pH adjusting agent Substances 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 150000004292 cyclic ethers Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008119 colloidal silica Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 2
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 2
- NOMOPRKYOOSZKV-UHFFFAOYSA-N 2-(diethoxymethylsilyl)ethyl-triethoxysilane Chemical compound CCOC(OCC)[SiH2]CC[Si](OCC)(OCC)OCC NOMOPRKYOOSZKV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- HITBDIPWYKTHIH-UHFFFAOYSA-N 2-[diethoxy(methyl)silyl]ethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CC[Si](C)(OCC)OCC HITBDIPWYKTHIH-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
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- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ATYUKIGQFAGPOB-UHFFFAOYSA-N CCOC(OCC)[SiH2]C[Si](OCC)(OCC)OCC Chemical compound CCOC(OCC)[SiH2]C[Si](OCC)(OCC)OCC ATYUKIGQFAGPOB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- VPLIEAVLKBXZCM-UHFFFAOYSA-N [diethoxy(methyl)silyl]-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)[Si](C)(OCC)OCC VPLIEAVLKBXZCM-UHFFFAOYSA-N 0.000 description 2
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- BOXVSHDJQLZMFJ-UHFFFAOYSA-N [dimethoxy(methyl)silyl]-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)[Si](C)(OC)OC BOXVSHDJQLZMFJ-UHFFFAOYSA-N 0.000 description 2
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- ZEJSBRIMTYSOIH-UHFFFAOYSA-N [dimethoxy(phenyl)silyl]-dimethoxy-phenylsilane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)[Si](OC)(OC)C1=CC=CC=C1 ZEJSBRIMTYSOIH-UHFFFAOYSA-N 0.000 description 2
- KCCVBXQGWAXUSD-UHFFFAOYSA-N [dimethoxy(phenyl)silyl]oxy-dimethoxy-phenylsilane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)O[Si](OC)(OC)C1=CC=CC=C1 KCCVBXQGWAXUSD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
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- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 2
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 2
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- ZPILIIPBPKDNTR-UHFFFAOYSA-N dimethoxymethyl(dimethoxymethylsilylmethyl)silane Chemical compound COC(OC)[SiH2]C[SiH2]C(OC)OC ZPILIIPBPKDNTR-UHFFFAOYSA-N 0.000 description 2
- AKPOQTZQHIWYJM-UHFFFAOYSA-N dimethoxymethylsilylmethyl(trimethoxy)silane Chemical compound COC(OC)[SiH2]C[Si](OC)(OC)OC AKPOQTZQHIWYJM-UHFFFAOYSA-N 0.000 description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- GPCIFOPQYZCLTR-UHFFFAOYSA-N ethoxy-[ethoxy(diphenyl)silyl]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si]([Si](OCC)(C=1C=CC=CC=1)C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 GPCIFOPQYZCLTR-UHFFFAOYSA-N 0.000 description 2
- QRZBTGCXOVMETC-UHFFFAOYSA-N ethoxy-[ethoxy(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OCC)O[Si](OCC)(C=1C=CC=CC=1)C1=CC=CC=C1 QRZBTGCXOVMETC-UHFFFAOYSA-N 0.000 description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 2
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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 2
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- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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- MRBRVZDGOJHHFZ-UHFFFAOYSA-N triethoxy-(3-triethoxysilylphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC([Si](OCC)(OCC)OCC)=C1 MRBRVZDGOJHHFZ-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-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
- 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
- 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
- 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
- SRFNOOYBAUZCIF-UHFFFAOYSA-N triphenylsilyloxysilicon Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O[Si])C1=CC=CC=C1 SRFNOOYBAUZCIF-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
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-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
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-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
- 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
- QCKKBOHAYRLMQP-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[SiH](OC(C)(C)C)OC(C)(C)C QCKKBOHAYRLMQP-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C09D183/02—Polysilicates
-
- 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
- C09D183/04—Polysiloxanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
- H01L21/02118—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 carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
-
- 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
-
- 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
본 발명은 낮은 비유전율을 갖고, 피도포물과의 사이의 밀착성이 우수한 도막을 형성할 수 있는 막 형성용 조성물 및 그의 제조 방법을 제공한다.
본 발명의 막 형성용 조성물은 (A) 하기 화학식 1 또는 화학식 2로 표시되는 실란 화합물로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매 존재하에서 가수분해, 축합하여 얻어지는 가수분해 축합물과,
(B) 산소 포함계 유기 용매
를 포함하고,
상기 (A)의 가수분해 축합물의 함유량이 5 중량% 미만이다.
<화학식 1>
RaSi(OR1)4-a
<화학식 2>
R2
b(R3O)3-bSi-(R6)d-Si(OR4)
3-cR5
c
식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이고, a는 0 내지 2의 정수이고,
R2 내지 R5는 동일 또는 상이하고, 각각 1가의 유기기를 나타내고, b 및 c는 동일또는 상이하고, O 내지 2의 수를 나타내고, R6은 산소 원자, 페닐렌기 또는 -(CH2)n-으로 표시되는 기 (여기서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
막 형성용 조성물, 실란 화합물, 알칼리 촉매, 가수분해, 축합
Description
본 발명은 막 형성용 조성물 및 그의 제조 방법에 관한 것이며, 특히 낮은 비유전율을 갖고, 실리카계 막과의 밀착성 및 유기계 막과의 밀착성이 우수한 막 형성용 조성물과 막 형성용 조성물의 제조 방법에 관한 것이다.
반도체 장치에 있어서의 층간 절연막으로서, CVD법 등의 진공 공정에 의해서 형성된 실리카 (SiO2)계 막 또는 유기 중합체를 주성분으로 하는 유기계 막이 사용되고 있다.
최근, 보다 균일한 층간 절연막을 형성하는 것을 목적으로 SOG (Spin on Glass) 막이라 불리는 테트라알콕시실란의 가수분해 생성물을 주성분으로 하는 도포형의 절연막이 사용되도록 되고 있다. 또한, 반도체 장치의 고집적화에 따라 유기 SOG라 불리는 오르가노폴리실록산을 주성분으로 하는 낮은 비유전율의 층간 절연막이 개발되고 있다.
한편, 반도체 장치의 한층 더 고집적화에 따른, 보다 우수한 도체 간의 전기 절연성이 요구되고 있고, 따라서, 보다 낮은 비유전율의 층간 절연막 재료를 구하도록 되었다.
그와 같은 층간 절연막 재료의 일례로서, 특허 문헌 1에 개시되어 있는 저비유전율의 절연막 형성용 도포형 조성물을 들 수 있다. 특허 문헌 1에 기재된 도막 형성용 조성물은 알콕시실란류를 금속 촉매 존재하에서 가수 분해 축합하여 얻어지는 것이다. 이 도막 형성용 조성물을 이용함으로써 저비유전율이고 또한 고탄성률이고, CMP 내성 등이 우수한 막을 얻을 수 있다.
<특허 문헌 1>
일본 특허 공개 2000-256621호 공보
최근의 반도체 장치의 제조 공정에서는, 적층막의 평탄화를 목적으로 CMP (Chemical Mechanical Polishing: 화학 기계적 연마) 공정이 다용되고 있다. 한편, 가공 공정의 간이화를 도모하기 위해서, 최근 실리카계 막 위에 유기계 막을 형성하는 것이 요구되고 있다. 그러나, 실리카계 막과 유기계 막과의 적층막에 대하여 CMP 등의 처리를 행하면 양자의 밀착성 부족의 원인에 의해, 실리카계 막과 유기계 막의 사이에서 막 박리가 발생하는 경우가 있었다.
본 발명의 목적은 낮은 비유전율을 갖고, 표면 거칠기가 커서 유기계 막과의 밀착성이 우수한 실리카계 막을 형성할 수 있는 막 형성용 조성물 및 그의 제조 방법을 제공하는 것에 있다.
본 발명의 막 형성용 조성물은 (A) 하기 화학식 1 또는 화학식 2로 표시되는 실란 화합물로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매 존재하에서 가수분해, 축합하여 얻어지는 가수분해 축합물과,
(B) 산소 포함계 유기 용매
를 포함하고,
상기 (A)의 가수분해 축합물의 함유량이 5 중량% 미만이다.
식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이고, a는 0 내지 2의 정수이고,
R2 내지 R5는 동일 또는 상이하고, 각각 1가의 유기기를 나타내고, b 및 c는 동일 또는 상이하고, O 내지 2의 수를 나타내고, R6은 산소 원자, 페닐렌기 또는 -(CH2)n-로 표시되는 기 (여기서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
본 발명의 막 형성용 조성물에 있어서, 상기 알칼리 촉매는 알칼리 금속 수 산화물, 암모니아, 알킬아민, 테트라알킬아민염으로부터 선택되는 1종 이상일 수 있다.
본 발명의 막 형성용 조성물에 있어서, 상기 산소 포함계 유기 용매는 비점 100 ℃ 내지 200 ℃일 수 있다.
본 발명의 막 형성용 조성물에 있어서, 상기 산소 포함계 유기 용매는 알킬렌글리콜, 알킬렌글리콜모노알킬에테르, 알킬렌글리콜디알킬에테르, 아세트산알킬렌글리콜모노알킬에테르, 환상 에테르, 환상 케톤으로부터 선택되는 1종 이상일 수 있다.
본 발명의 막 형성용 조성물의 제조 방법은, 하기 화학식 1 또는 화학식 2로 표시되는 실란 화합물로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매, 물, 탄소수 3 이하의 알코올의 존재하에서 가수분해, 축합한 후, 산소 포함계 유기 용매를 가하는 것을 포함한다.
<화학식 1>
RaSi(OR1)4-a
<화학식 2>
R2
b(R3O)3-bSi-(R6)d-Si(OR4)
3-cR5
c
식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이고, a는 0 내지 2의 정수이고,
R2 내지 R5는 동일 또는 상이하고, 각각 1가의 유기기를 나타내고, b 및 c는 동일또는 상이하고, O 내지 2의 수를 나타내고, R6은 산소 원자, 페닐렌기 또는 -(CH2)n-로 표시되는 기 (여기서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
본 발명의 막 형성용 조성물의 제조 방법은, 상기 화학식 1 또는 화학식 2로 표시되는 실란 화합물로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매, 물, 탄소수 3 이하의 알코올 및 산소 포함계 유기 용매의 존재하에서 가수분해, 축합하는 것을 포함한다.
<발명을 실시하기 위한 최선의 형태>
이하, 본 발명의 막 형성용 조성물 및 그의 제조 방법에 대하여 구체적으로 설명한다.
1. 막 형성용 조성물
본 발명의 막 형성용 조성물은,
(A) 하기 화학식 1로 표시되는 실란 화합물 (이하 「화합물 1」이라고 한다) 또는 화학식 2로 표시되는 실란 화합물 (이하 「화합물 2」라고 한다)로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매 존재하에서 가수분해, 축합하여 얻어지는 가수분해 축합물과,
(B) 산소 포함계 유기용매
를 포함하고,
상기 (A)의 가수분해 축합물의 함유량이 5 중량% 미만이다.
<화학식 1>
RaSi(OR1)4-a
<화학식 2>
R2
b(R3O)3-bSi-(R6)d-Si(OR4)
3-cR5
c
식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이고, a는 0 내지 2의 정수이고,
R2 내지 R5는 동일 또는 상이하고, 각각 1가의 유기기를 나타내고, b 및 c는 동일 또는 상이하고, O 내지 2의 수를 나타내고, R6은 산소 원자, 페닐렌기 또는 -(CH2)n-로 표시되는 기 (여기서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
본 발명에 있어서 「가수분해물」이란 상기 화합물 1 및 2로부터 선택된 1종 이상의 실란 화합물에 포함되는 알콕시기의 전부가 가수분해되어 있을 필요는 없고, 예를 들면 1 개만이 가수분해되어 있는 것, 2 개 이상이 가수분해되어 있는 것, 또는 이들의 혼합물일 수도 있다. 또한, 여기서, 「축합물」이란 상기 화합물 1 및 2의 가수분해물의 실라놀기가 축합하여 Si-O-Si 결합을 형성한 것이지만, 본 발명에서는 실라놀기가 전부 축합하고 있을 필요는 없고, 약간의 일부의 실라놀기가 축합한 것, 축합의 정도가 다른 것의 혼합물 등까지도 포함한 개념이다.
1.1 (A) 성분
(화합물 1)
상기 화학식 1에 있어서, R 및 R1의 1가의 유기기로서는 알킬기, 아릴기, 알릴기, 글리시딜기 등을 들 수 있다. 그 중에서도 화학식 1에 있어서, R은 1가의 유기기, 특히 알킬기 또는 페닐기인 것이 바람직하다. 여기서, 알킬기로서는 메틸기, 에틸기, 프로필기, 부틸기 등을 들 수 있고, 바람직하게는 탄소수 1 내지 5이고, 이러한 알킬기는 쇄상 또는 분지상일 수도 있고, 또한 수소 원자가 불소 원자 등으로 치환될 수도 있다. 화학식 1에 있어서, 아릴기로서는 페닐기, 나프틸기, 메틸페닐기, 에틸페닐기, 클로로페닐기, 브로모페닐기, 플루오로페닐기 등을 들 수 있다.
화합물 1의 구체적인 예로서는 트리메톡시실란, 트리에톡시실란, 트리-n-프로폭시실란, 트리-이소-프로폭시실란, 트리-n-부톡시실란, 트리-sec-부톡시실란, 트리-tert-부톡시실란, 트리페녹시실란, 플루오로트리메톡시실란, 플루오로트리에톡시실란, 플루오로트리-n-프로폭시실란, 플루오로트리-이소-프로폭시실란, 플루오로트리-n-부톡시실란, 플루오로트리-sec-부톡시실란, 플루오로트리-tert-부톡시실란, 플루오로트리페녹시실란 등;
메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-이소-프로폭시실란, 메틸트리-n-부톡시실란, 메틸트리-sec-부톡시실란, 메틸트 리-tert-부톡시실란, 메틸트리페녹시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 에틸트리-n-프로폭시실란, 에틸트리-이소-프로폭시실란, 에틸트리-n-부톡시실란, 에틸트리-sec-부톡시실란, 에틸트리-tert-부톡시실란, 에틸트리페녹시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 비닐트리-n-프로폭시실란, 비닐트리-이소-프로폭시실란, 비닐트리-n-부톡시실란, 비닐트리-sec-부톡시실란, 비닐트리-tert-부톡시실란, 비닐트리페녹시실란, n-프로필트리메톡시실란, n-프로필트리에톡시실란, n-프로필트리-n-프로폭시실란, n-프로필트리-이소-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-이소-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-이소-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-이소-프로폭시실란, sec-부틸-트리-n-부톡시실란, sec-부틸-트리-sec-부톡시실란, sec-부틸-트리-tert-부톡시실란, sec-부틸-트리페녹시실란, t-부틸트리메톡시실란, t-부틸트리에톡시실란, t-부틸트리-n-프로폭시실란, t-부틸트리-이소-프로폭시실란, t-부틸트리-n-부톡시실란, t-부틸트리-sec-부톡시실란, t-부틸트리-tert-부톡시실란, t-부틸트리페녹시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 페닐트 리-n-프로폭시실란, 페닐트리-이소-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-이소-프로폭시실란, 디메틸-디-n-부톡시실란, 디메틸-디-sec-부톡시실란, 디메틸-디-tert-부톡시실란, 디메틸디페녹시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디에틸-디-n-프로폭시실란, 디에틸-디-이소-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-이소-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-이소-프로필디메톡시실란, 디-이소-프로필디에톡시실란, 디-이소-프로필-디-n-프로폭시실란, 디-이소-프로필-디-이소-프로폭시실란, 디-이소-프로필-디-n-부톡시실란, 디-이소-프로필-디-sec-부톡시실란, 디-이소-프로필-디-tert-부톡시실란, 디-이소-프로필-디-페녹시실란, 디-n-부틸디메톡시실란, 디-n-부틸디에톡시실란, 디-n-부틸-디-n-프로폭시실란, 디-n-부틸-디-이소-프로폭시실란, 디-n-부틸-디-n-부톡시실란, 디-n-부틸-디-sec-부톡시실란, 디-n-부틸-디-tert-부톡시실 란, 디-n-부틸-디-페녹시실란, 디-sec-부틸디메톡시실란, 디-sec-부틸디에톡시실란, 디-sec-부틸-디-n-프로폭시실란, 디-sec-부틸-디-이소-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-이소-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-이소-프로폭시실란, 디페닐-디-n-부톡시실란, 디페닐-디-sec-부톡시실란, 디페닐-디-tert-부톡시실란, 디페닐디페녹시실란, 디비닐트리메톡시실란 등을 들 수 있다.
화합물 1로서 바람직한 화합물은 테트라메톡시실란, 테트라에톡시실란, 테트라-n-프로폭시실란, 테트라-이소-프로폭시실란, 테트라-n-부톡시실란, 테트라-sec-부톡시실란, 테트라-tert-부톡시실란, 테트라페녹시실란, 메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리-n-프로폭시실란, 메틸트리-이소-프로폭시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 디메틸디메톡시실란, 디메틸디에톡시실란, 디에틸디메톡시실란, 디에틸디에톡시실란, 디페닐디메톡시실란, 디페닐디에톡시실란 등이다.
이러한 화합물은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
(화합물 2)
상기 화학식 2에 있어서, R2 내지 R5로 표시되는 1가의 탄화수소기로서는, 상기 화학식 1에서 나타낸 것과 동일한 탄화수소기를 들 수 있다.
화학식 2에 있어서의 R6이 산소 원자인 화합물로서는, 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-펜타페녹시-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-디페 녹시-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 중, 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-디에톡시-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, 화학식 2에 있어서, d가 0인 화합물로서는, 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, 화학식 2에 있어서, R6이 -(CH2)n-으로 표시되는 기의 화합물로서는 비스(트리메톡시실릴)메탄, 비스(트리에톡시실릴)메탄, 비스(트리-n-프로폭시실릴)메탄, 비스(트리-이소-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-이소-프로폭시실릴)에탄, 1,2-비스(트리-n-부톡시실릴)에탄, 1,2-비스(트리-sec-부톡시실릴)에탄, 1,2-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-이소-프로폭시메틸실릴)-1-(트리-이소-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-이소-프로폭시메틸실릴)-2-(트리-이소-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-이소-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-이소-프로폭시메틸실릴)에탄, 1,2-비스(디-n-부톡시메틸실릴)에탄, 1,2-비스(디-sec-부톡시메틸실릴)에탄, 1,2-비스(디-t-부톡시메틸실릴)에탄 등을 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-(트 리에톡시실릴)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 등을 바람직한 예로서 들 수 있다.
또한, 화학식 2에 있어서, R6이 페닐렌기로 표시되는 기의 화합물로서는 1,2-비스(트리메톡시실릴)벤젠, 1,2-비스(트리에톡시실릴)벤젠, 1,2-비스(트리-n-프로폭시실릴)벤젠, 1,2-비스(트리-이소-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-이소-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(트리에톡시실릴)벤젠, 1,4-비스(트리-n-프로폭시실릴)벤젠, 1,4-비스(트리-이소-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, 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.
본 발명에 있어서는, 실란 화합물로서는 상기 화합물 (1) 및 (2)의 1종 또는 2종 이상을 사용할 수 있다.
(알칼리 촉매)
본 발명에 있어서는, 상술한 화합물 (1) 및 (2)로부터 선택되는 실란 화합물을 가수분해 축합할 때, 알칼리 촉매의 존재하에서 행할 수 있다. 사용할 수 있는 알칼리 촉매로서는 알칼리 금속 수산화물, 암모니아, 알킬아민, 테트라알킬아민염으로부터 선택되는 1종 이상을 들 수 있다.
알칼리 금속 수산화물로서는, 수산화나트륨, 수산화칼륨, 수산화바륨, 수산화칼슘 등을 들 수 있다.
알킬아민으로서는, 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-메틸 디에탄올아민, 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, 테트라메틸에틸렌디아민, 테트라에틸에틸렌디아민, 테트라프로필에틸렌디아민, 테트라부틸에틸렌디아민, 메틸아미노메틸아민, 메틸아미노에틸아민, 메틸아미노프로필아민, 메틸아미노부틸아민, 에틸아미노메틸아민, 에틸아미노에틸아민, 에틸아미노프로필아민, 에틸아미노부틸아민, 프로필아미노메틸아민, 프로필아미노에틸아민, 프로필아미노프로필아민, 프로필아미노부틸아민, 부틸아미노메틸아민, 부틸아미노에틸아민, 부틸아미노프로필 아민, 부틸아미노부틸아민, 피리딘, 피롤, 피페라진, 피롤리딘, 피페리딘, 피콜린, 모르폴린, 메틸모르폴린, 디아자비시클로옥탄, 디아자비시클로노난, 디아자비시클로운데센 등을 들 수 있다.
테트라알킬아민염으로서는, 테트라메틸암모늄히드록시드, 테트라에틸암모늄히드록시드, 테트라프로필암모늄히드록시드, 테트라부틸암모늄히드록시드, 벤질트리메틸암모늄히드록시드 등을 들 수 있다.
상기 알칼리 촉매의 사용량은 화합물 1 및 2 중의 R1O기, R3O기 및 R4O기의 총량 1 몰에 대하여 통상 0.00001 내지 0.5 몰, 바람직하게는 0.00001 내지 0.3 몰이다. (A) 성분이 화합물 1, 2의 축합물인 경우에는 그 분자량은 폴리스티렌 환산의 중량 평균 분자량으로 통상적으로 500 내지 1,000,000, 바람직하게는 700 내지 500,000, 더욱 바람직하게는 1,000 내지 300,000 정도이다.
1.2 (B) 성분
본 발명의 막 형성용 조성물에 있어서, (B) 산소 포함계 유기 용매로서는 그 비점이 바람직하게는 100 ℃ 내지 200 ℃이고, 보다 바람직하게는 100 내지 190 ℃의 용매를 이용한다. 비점이 상기 범위를 벗어날 경우에는 막 형성용 조성물의 도포성이 악화하여 균질한 도막이 얻어지지 않는 경우가 있어 바람직하지 않다.
(B) 산소 포함계 유기 용매로서는 골격 중에 1 개 이상의 산소 원자를 포함하는 화합물이면 특별히 제한되지 않고 사용할 수 있지만, 바람직하게는 알킬렌글리콜, 알킬렌글리콜모노알킬에테르, 알킬렌글리콜디알킬에테르, 아세트산알킬렌글 리콜모노알킬에테르, 환상 에테르, 환상 케톤을 사용할 수 있다.
알킬렌글리콜로서는, 에틸렌글리콜, 1,2-프로필렌글리콜, 1,3-프로필렌글리콜, 1,3-부틸렌글리콜, 1,4-부틸렌글리콜, 펜탄디올-2,4,2-메틸펜탄디올-2,4, 헥산디올-2,5, 헵탄디올-2,4, 2-에틸헥산디올-1,3, 디에틸렌글리콜, 디프로필렌글리콜, 트리에틸렌글리콜, 트리프로필렌글리콜 등을 들 수 있다.
알킬렌글리콜모노알킬에테르로서는, 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노프로필에테르, 에틸렌글리콜모노부틸에테르, 에틸렌글리콜모노헥실에테르, 에틸렌글리콜모노페닐에테르, 에틸렌글리콜모노-2-에틸부틸에테르, 디에틸렌글리콜모노메틸에테르, 디에틸렌글리콜모노에틸에테르, 디에틸렌글리콜모노프로필에테르, 디에틸렌글리콜모노부틸에테르, 디에틸렌글리콜모노헥실에테르, 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노에틸에테르, 프로필렌글리콜모노프로필에테르, 프로필렌글리콜모노부틸에테르, 디프로필렌글리콜모노메틸에테르, 디프로필렌글리콜모노에틸에테르, 디프로필렌글리콜모노프로필에테르 등을 들 수 있다.
알킬렌글리콜디알킬에테르로서는, 프로필렌글리콜디메틸에테르, 프로필렌글리콜디에틸에테르, 프로필렌글리콜디프로필에테르, 프로필렌글리콜디부틸에테르, 디프로필렌글리콜디메틸에테르, 디프로필렌글리콜디에틸에테르, 디프로필렌글리콜디프로필에테르, 디프로필렌글리콜디부틸에테르 등을 들 수 있다.
아세트산알킬렌글리콜모노알킬에테르로서는, 아세트산에틸렌글리콜모노메틸에테르, 아세트산에틸렌글리콜모노에틸에테르, 아세트산에틸렌글리콜모노프로필에 테르, 아세트산에틸렌글리콜모노부틸에테르, 아세트산프로필렌글리콜모노메틸에테르, 아세트산프로필렌글리콜모노에틸에테르, 아세트산프로필렌글리콜모노프로필에테르, 아세트산프로필렌글리콜모노부틸에테르, 아세트산부틸렌글리콜모노메틸에테르, 아세트산부틸렌글리콜모노에틸에테르, 아세트산부틸렌글리콜모노프로필에테르, 아세트산부틸렌글리콜모노부틸에테르, 아세트산디에틸렌글리콜모노메틸에테르, 아세트산디에틸렌글리콜모노에틸에테르, 아세트산디에틸렌글리콜모노프로필에테르, 아세트산디에틸렌글리콜모노부틸에테르, 아세트산디프로필렌글리콜모노메틸에테르, 아세트산디프로필렌글리콜모노에틸에테르, 아세트산디프로필렌글리콜모노프로필에테르, 아세트산디프로필렌글리콜모노부틸에테르 등을 들 수 있다.
환상 에테르로서는, 테트라히드로푸란, 2-메틸테트라히드로푸란 등을 들 수 있다.
환상 케톤으로서는, 시클로헥사논, 메틸시클로헥사논, 포론, 이소포론, γ-부티로락톤 등을 들 수 있다.
상술한 유기 용매 중 1종 또는 2종 이상을 동시에 사용할 수도 있다.
본 발명에서는 특히 환상 에테르 및(또는) 환상 케톤을 사용하는 것이 바람직하다.
또한, 본 발명의 계 막 형성용 조성물로서는, 최종적인 조성물의 pH를 7 이하로 조정하는 것이 바람직하다. pH를 조정하는 방법으로서는 (a) pH 조정제를 첨가하는 방법, (b) 상압 또는 감압하에서 조성물 중 보다 알칼리 촉매를 증류 제거하는 방법, (c) 질소, 아르곤 등의 가스를 버블링함으로써 조성물 중에서 알칼리 촉매를 제거하는 방법, (d) 이온 교환 수지에 의해 조성물 중에서 알칼리성 촉매를 제거하는 방법, (e) 추출이나 세정에 의해서 알칼리성 화합물을 계 밖으로 제거하는 방법 등을 들 수 있다. 이러한 방법은 각각 조합하여 사용할 수도 있다.
여기서, 상기 pH 조정제로서는 무기산이나 유기산을 들 수 있다. 무기산으로서는, 예를 들면 염산, 질산, 황산, 불산, 인산, 붕산, 옥살산 등을 들 수 있다. 또한, 유기산으로서는, 예를 들면 아세트산, 프로피온산, 부탄산, 펜탄산, 헥산산, 헵탄산, 옥탄산, 노난산, 데칸산, 옥살산, 말레산, 메틸말론산, 아디프산, 세바스산, 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, 글루타르산의 가수분해물, 무수 말레산의 가수분해물, 무수 프탈산의 가수분해물 등을 들 수 있다. 이들 화합물은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
상기 pH 조정제에 의한 조성물의 pH는 7 이하, 바람직하게는 1 내지 6으로 조정된다. 상기 pH 조정제에 의해 상기 범위 내에 pH를 조정함으로써 얻어지는 조성물의 저장 안정성이 향상되는 효과가 얻어진다. pH 조정제의 사용량은 조성물의 pH가 상기 범위 내가 되는 양이고, 그 사용량은 적절하게 선택된다.
1.3 그 밖의 첨가물
본 발명의 막 형성용 조성물에는 또한 콜로이드상 실리카, 콜로이드상 알루 미나, 계면활성제, 실란 커플링제 등의 성분을 첨가할 수도 있다. 콜로이드상 실리카란 예를 들면 고순도의 무수 규산을 상기 친수성 유기 용매에 분산한 분산액이고, 통상적으로 평균 입경이 5 내지 30 nm, 바람직하게는 10 내지 20 nm, 고형분 농도가 10 내지 40 중량% 정도의 것이다. 이러한 콜로이드상 실리카로서는, 예를 들면 닛산 가가꾸 고교(주)제, 메탄올실리카졸 및 이소프로판올실리카졸; 쇼꾸바이 가가꾸 고교(주)제, 오스칼 등을 들 수 있다. 콜로이드상 알루미나로서는, 닛산 가가꾸 고교(주)제의 알루미나졸 520, 동 100, 동 200; 가와깽 화인 케미칼(주)제의 알루미나 클리어 졸, 알루미나졸 10, 동 132 등을 들 수 있다.
계면활성제로서는, 예를 들면 비이온계 계면활성제, 음이온계 계면활성제, 양이온계 계면활성제, 양성 계면활성제 등을 들 수 있고, 또한 불소계 계면활성제, 실리콘계 계면활성제, 폴리알킬렌옥시드계 계면활성제, 폴리(메트)아크릴레이트계 계면활성제 등을 들 수 있고, 바람직하게는 불소계 계면활성제, 실리콘계 계면활성제를 들 수 있다.
불소계 계면활성제로서는, 예를 들면 1,1,2,2-테트라플루오로옥틸(1,1,2,2-테트라플루오로프로필)에테르, 1,1,2,2-테트라플루오로옥틸헥실에테르, 옥타에틸렌글리콜디(1,1,2,2-테트라플루오로부틸)에테르, 헥사에틸렌글리콜(1,1,2,2,3,3-헥사플루오로펜틸)에테르, 옥타프로필렌글리콜디(1,1,2,2-테트라플루오로부틸)에테르, 헥사프로필렌글리콜디(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, 퍼플루오로알킬술폰아미드프로필트리메틸암모늄염, 퍼플루오로알킬-N-에틸술포닐글리신염, 인산비스(N-퍼플루오로옥틸술포닐-N-에틸아미노에틸), 모노퍼플루오로알킬에틸 인산 에스테르 등의 말단, 주쇄 및 측쇄의 적어도 어느 하나의 부위에 플루오로알킬 또는 플루오로알킬렌기를 갖는 화합물을 포함하는 불소계 계면활성제를 들 수 있다. 또한, 시판품으로서는 메가팩 F142D, 동 F172, 동 F173, 동 F183 (이상, 다이닛본 잉크 가가꾸 고교(주)제), 에프톱 EF 301, 동 303, 동 352 (신아끼다 가세이(주)제), 플로우라이드 FC-430, 동 FC-431 (스미토모 쓰리엠(주)제), 아사히가드 AG 710, 서프론 S-382, 동 SC-101, 동 SC-102, 동 SC-103, 동 SC-104, 동 SC-105, 동 SC-106 (아사히 가라스(주)제), BM-1000, BM-1100 (유쇼(주)제), NBX-15((주) 네오스) 등의 명칭으로 시판되어 있는 불소계 계면활성제를 들 수 있다. 그 중에서도 상기 메가팩 F 172, BM-1000, BM-1100, NBX-15가 특히 바람직하다.
실리콘계 계면활성제로서는, 예를 들면 SH7PA, SH21PA, SH30PA, ST94PA (모두 도레ㆍ다우코닝ㆍ실리콘(주)제) 등을 사용할 수 있다. 그 중에서도 상기 SH28PA, SH30PA가 특히 바람직하다. 계면활성제의 사용량은 (A) 성분 (완전 가수분해 축합물)에 대하여 통상 0.0001 내지 10 중량부이다. 이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
실란 커플링제로서는, 예를 들면 3-글리시딜옥시프로필트리메톡시실란, 3-아미노글리시딜옥시프로필트리에톡시실란, 3-메타크릴옥시프로필트리메톡시실란, 3-글리시딜옥시프로필메틸디메톡시실란, 1-메타크릴옥시프로필메틸디메톡시실란, 3- 아미노프로필트리메톡시실란, 3-아미노프로필트리에톡시실란, 2-아미노프로필트리메톡시실란, 2-아미노프로필트리에톡시실란, N-(2-아미노에틸)-3-아미노프로필트리메톡시실란, N-(2-아미노에틸)-3-아미노프로필메틸디메톡시실란, 3-우레이도프로필트리메톡시실란, 3-우레이도프로필트리에톡시실란, N-에톡시카르보닐-3-아미노프로필트리메톡시실란, N-에톡시카르보닐-3-아미노프로필트리에톡시실란, N-트리에톡시실릴프로필트리에틸렌트리아민, N-트리에톡시실릴프로필트리에틸렌트리아민, 10-트리메톡시실릴-1,4,7-트리아자데칸, 10-트리에톡시실릴-1,4,7-트리아자데칸, 9-트리메톡시실릴-3,6-디아자노닐아세테이트, 9-트리에톡시실릴-3,6-디아자노닐아세테이트, N-벤질-3-아미노프로필트리메톡시실란, N-벤질-3-아미노프로필트리에톡시실란, N-페닐-3-아미노프로필트리메톡시실란, N-페닐-3-아미노프로필트리에톡시실란, N-비스(옥시에틸렌)-3-아미노프로필트리메톡시실란, N-비스(옥시에틸렌)-3-아미노프로필트리에톡시실란 등을 들 수 있다. 이들은 1종 또는 2종 이상을 동시에 사용할 수도 있다.
본 발명의 막 형성용 조성물의 전체 고형분 농도는 바람직하게는 0.1 내지 5 중량%이고, 사용 목적에 따라서 적절하게 조정된다. 본 발명의 막 형성용 조성물의 전체 고형분 농도가 0.1 내지 5 중량%인 것에 의해, 도막의 막 두께가 적당한 범위가 되고, 보다 우수한 보존 안정성을 갖는 것이 된다. 또한, 이 전체 고형분 농도의 조정은 필요하면 농축 또는 산소 포함계 유기 용매로서 예시한 용제 또는 다른 용제에 의한 희석에 의해서 행하여진다.
2. 막 형성용 조성물의 제조 방법
본 발명의 막 형성용 조성물의 제조 방법으로서는, 우선 상술한 화합물1 또는 화합물 2로부터 선택되는 적어도 1종의 실란 화합물을 상술한 알칼리 촉매, 물, 유기 용제의 존재하에서 가수분해 축합을 행한다.
본 발명의 제조 방법에 있어서, 이용되는 유기 용제로서는 탄소수 3 이하의 알코올을 사용한다. 탄소수 3 이하의 알코올로서는 메탄올, 에탄올, n-프로판올, 이소프로판올 등을 들 수 있다. 유기 용제로서 탄소수 3 이하의 알코올을 사용하는 것으로써 중합체의 석출이나 겔화 등이 생기는 일 없이 안정적으로 화합물 1 및(또는) 화합물 2의 가수분해 축합 반응을 행할 수 있다는 이점이 있다.
본 발명의 막 형성용 조성물의 제조 방법에 있어서, 화합물 1 또는 2로부터 선택되는 실란 화합물을 가수분해 축합하는 방법으로서는 특별히 한정되지 않지만 구체적으로는 예를 들면 하기 1) 내지 4)의 형태를 들 수 있다.
1) 유기 용제, 알칼리 촉매 및 물을 포함하는 혼합물에 화합물 1 또는 2로부터 선택되는 실란 화합물을 가하여 가수분해 축합 반응을 행하는 방법.
2) 유기 용제, 알칼리 촉매 및 물을 포함하는 혼합물에 화합물 1 또는 2로부터 선택되는 실란 화합물을 연속적 또는 단속적으로 첨가하여 가수분해 축합 반응을 행하는 방법.
3) 유기 용제, 알칼리 촉매 및 화합물 1 또는 2로부터 선택되는 실란 화합물을 포함하는 혼합물에 유기 용제 및 물을 일괄 또는 연속적 또는 단속적으로 첨가하여 가수분해 축합 반응을 행하는 방법.
4) 유기 용제, 화합물 1 또는 2로부터 선택되는 실란 화합물 및 물을 포함하 는 혼합물에 알칼리 촉매를 가하여 가수분해 축합 반응을 행하는 방법.
또한, 반응계 내에서 화합물 1 또는 2로부터 선택되는 실란 화합물의 농도는 0.1 내지 30 중량%로 조정되는 것이 바람직하다. 반응계 내의 각 성분의 농도가 상기 범위를 벗어나면 가수분해 축합 반응이 충분히 진행하지 않는 경우나 반응 중에 겔화가 생기는 경우가 있어 바람직하지 않다.
상술한 공정에 의해 가수분해 축합 반응을 끝낸 후에, (B) 성분인 상술한 산소 포함계 유기 용매를 가한다. 이 때, (A) 성분의 가수분해 축합물의 함유량은 바람직하게는 0.1 내지 5 중량%, 보다 바람직하게는 0.3 내지 5 중량%가 되도록 한다. 이와 같이, (A) 성분의 함유량을 상기 범위로 한정함으로써 도막의 막 두께가 적당한 범위가 되고, 보다 우수한 보존 안정성을 갖는 것이 된다. 상기 공정에 의해 제조된 막 형성용 조성물은 도막을 형성하였을 때의 표면 거칠기를 크게 할 수 있다. 표면 거칠기는 바람직하게는 10 nm 이상이다. 그 때문에, 예를 들면 유기계 막과 적층하였을 때, 유기계 막이 본 발명의 막 형성용 조성물을 사용하여 얻어진 도막에 들어가는 앵커 (anchor) 효과에 의해 밀착성을 향상시킬 수 있는 것이다.
또한, (B) 성분으로서 산소 포함계 유기 용제는 본 발명에 기재된 가수분해 축합물에 대한 적절한 용해성을 갖고, 또한 적절한 비점을 갖는 것으로 도막 형성 시에 적절한 증발 속도가 얻어지기 때문에 보존 안정성이 우수하고, 양호한 도막이 얻어지는 막 형성용 조성물을 얻을 수 있다.
상술한 막 형성용 조성물의 제조 방법으로서는, 화합물 1 및 2로부터 선택되 는 실란 화합물을 가수분해 축합한 후에 (B) 성분의 산소 포함계 유기 용매를 가하는 방법에 대해서 설명하였지만, 이 외에 화합물 1 및 2로부터 선택되는 실란 화합물을 가수분해 축합할 때의 유기 용제로서 탄소수 3 이하의 알코올과 (B) 성분의 산소 포함계 유기 용매가 혼합된 용제를 이용하여 행할 수도 있다.
본 발명의 막 형성용 조성물에 의해 얻어지는 실리카계 막은 유전율 특성 및 보존 안정성이 우수하고, 층간 절연막용 재료로서 바람직한 것이다. 또한, 표면 거칠기가 크기 때문에 본 발명의 실리카계 막과 유기계 막을 적층한 경우에 밀착성이 향상된 적층체를 얻을 수 있다. 또한, 조성이 유사한 다른 실리카계 막과 적층할 경우에도 양호하게 밀착될 수가 있다. 그 때문에, 유기계 막과, 유기계 막과 직접 적층하면 양호한 밀착성이 얻어지지 않는 다른 실리카계 막과의 사이에 본 발명의 실리카계 막을 통하는 것으로써, 밀착성이 향상된 절연성의 적층체를 얻을 수있다.
예를 들면, a) 실리카계 절연막 위에 제1항에 기재된 막 형성용 조성물을 도포하고, 건조한 후, b) 상기 a)에서 얻어진 막 위에 또한 유기계 절연막을 형성함으로써, 종래의 실리카계 절연막과 유기계 절연막의 밀착성을 향상시킬 수 있다.
여기서, 종래의 실리카계 절연막은 메틸폴리실록산이나 수소 폴리실록산 등의 용액을 스핀 코팅하고 가열하여 얻어지는 막이나, CVD법에 의해 얻어지는 막 등을 들 수 있다.
또한 유기계 절연막으로서는 비유전율이 3.5 미만인 폴리에테르, 폴리벤즈이미다졸, 폴리이미드 등을 들 수 있다.
본 발명의 실리카계 막은 상술한 이점을 갖기 위해서 LSI, 시스템 LSI, DRAM, SDRAM, RDRAM, D-RDRAM 등의 반도체 장치용 층간 절연막, 반도체 장치의 표면 코팅막 등의 보호막, 다층 레지스트를 사용한 반도체 제조 공정의 중간층, 다층 배선 기판의 층간 절연막, 액정 표시 장치용의 보호막이나 절연막 등의 용도로 유용하다.
<실시예>
이하, 본 발명을 실시예를 들어 더욱 구체적으로 설명한다. 단, 이하의 기재는 본 발명의 형태예를 개괄적으로 나타내는 것으로, 특별히 이유 없고, 이러한 기재에 의해 본 발명은 한정되는 것이 아니다. 또한 실시예 및 비교예 중의 부 및 %는 특기하지 않는 한, 각각 중량부 및 중량%인 것을 나타내고 있다. 본 실시예에서는 본 발명에 따른 막 형성용 조성물 1 내지 3과, 막 형성용 조성물 1 내지 3의 밀착성을 확인하기 위해서 다른 실리카계 막을 형성하기 위한 막 형성용 조성물 및 유기계 막을 형성하기 위한 막 형성용 조성물을 형성하였다. 또한, 각종의 평가는 다음과 같이 하여 행하였다.
(보존 안정성)
40 ℃에서 30 일 보존한 막 형성용 조성물을 스핀 코팅법을 이용하여 기재에 도포하고, 핫 플레이트 상에서 90 ℃에서 3 분간, 질소 분위기하 200 ℃에서 3분간 기판을 건조하고, 또한 50 mTorr의 감압하 420 ℃의 종형 퍼니스로 1 시간 소성하였다. 이와 같이 하여 얻어진 도막의 막 두께를, 광학식 막후계 (루돌프 테크놀로지스 (Rudolph Technologies)사제, 스펙트라 레이저 (Spectra Laser) 200)를 이용 하여 도막면 내에서 50 점 측정하였다. 얻어진 막 두께의 막 두께를 측정하여 하기 식에 의해 구한 막 두께 증가율에 의해 보존 안정성을 평가하였다.
막 두께 증가율 (%)=((보존 후의 막 두께)-(보존 전의 막 두께))÷(보존 전의 막 두께)×100
○: 막 두께 증가율 4 % 이하
×: 막 두께 증가율 4 % 초과
(비유전율 측정)
8 인치 실리콘 웨이퍼 상에 스핀 코팅법을 이용하여 막 형성용 조성물을 도포하고, 핫 플레이트 상에서 90 ℃에서 3 분간, 질소 분위기하 200 ℃에서 3 분간 건조하고, 또한 50 mTorr의 감압하 (진공 분위기) 420 ℃의 종형 퍼니스로 1 시간 소성하였다. 얻어진 막에 증착법에 의해 알루미늄 전극 패턴을 형성시켜 비유전율 측정용 샘플을 제조하였다. 이 샘플을 주파수 100 kHz의 주파수로, 요꼬가와?휴렛 팩커드(주)제, HP 16451B 전극 및 HP 4284A 프래시전 LCR 미터를 이용하여 CV법에 의해 해당 도막의 비유전율을 측정하였다.
(도막의 표면 거칠기)
8 인치 실리콘 웨이퍼 상에 스핀 코팅법을 이용하여 막 형성용 조성물을 도포하고, 핫 플레이트 상에서 90 ℃에서 3 분간, 질소 분위기하 200 ℃에서 3 분간 건조하고, 또한 50 mTorr의 감압하 (진공 분위기) 420 ℃의 종형 퍼니스로 1 시간을 소성하였다. 얻어진 막의 표면 거칠기 (Rmax)를 디지탈 인스트루먼트사제, 나노스코프 (Nanoscope) IIIa를 사용하여 탑핑 모드에 의해 측정하였다.
(밀착성)
8 인치 실리콘 웨이퍼 상에 스핀 코팅법을 이용하여 후술하는 다른 실리카계 막을 위한 막 형성용 조성물을 도포하고, 핫 플레이트 상에서 90 ℃에서 3 분간, 질소 분위기하 200 ℃에서 3 분간 건조하고, 또한 50 mTorr의 감압하 420 ℃의 종형 퍼니스로 1 시간 소성하였다. 계속해서 본 실시예 및 비교예에 관한 막 형성용 조성물을 스핀 코팅법을 이용하여 도포하고, 핫 플레이트 상에서 90 ℃에서 3 분간, 질소 분위기하 200 ℃에서 3 분간 건조하였다. 또한 후술하는 유기계 막 형성용 조성물을 스핀 코팅법을 이용하여 도포하고, 핫 플레이트 상에서 90 ℃에서 3 분간, 질소 분위기하 200 ℃에서 3 분간 건조하고, 또한 50 mTorr의 감압하 420 ℃의 종형 퍼니스로 1 시간 소성하여, 다른 실리카계 막/본 실시예 및 비교예에 관한 막 형성용 조성물에 의해 얻어진 실리카계 막/유기계 막이 각각 500 nm/50 nm/500 nm의 막 두께로 적층된 적층막을 얻었다. 얻어진 적층막 상에 에폭시 수지를 사용하여 스터드 핀 10 개를 고정하여 150 ℃에서 1 시간 건조시켰다. 이 스터드 핀을 세바스찬법을 이용하여 방출 시험을 행하고 박리면을 관찰하여 이하의 기준으로 밀착성을 평가하였다.
○: 다른 실리카계 막/실시예의 실리카계 막/유기 막의 계면에서의 박리가 20 % 미만
×: 다른 실리카계 막/실시예의 실리카계 막/유기 막의 계면에서의 박리가 20 % 이상
<실시예 1>
석영제 분리 플라스크 중에서, 15 % 수산화 테트라메틸암모늄 수용액100.00 g, 초순수 300.00 g 및 에탄올 500.00 g을 혼합하고, 계속해서 메틸트리메톡시실란 136.22 g과 테트라에톡시시실란 208.33 g을 가하고, 60 ℃에서 5 시간 교반하였다. 반응액에 시클로헥사논 1500.00 g을 가한 후, 증발기로 1272 g (고형분 함유량 10 % 상당)으로 농축하고, 질산의 10 % 시클로헥사논 용액150.00 g과 시클로헥사논 4950.00 g을 가하고, 0.2 마이크론 공경의 테프론제 필터로 여과하여 고형분 함유량 약 2 %의 막 형성용 조성물 1을 얻었다.
<실시예 2>
석영제 분리 플라스크 중에서, 10 % 수산화 테트라메틸암모늄 수용액100.00 g, 초순수 1000.00 g 및 이소프로필알코올 1000.00 g을 혼합하고, 계속해서 메틸트리메톡시실란 136.22 g과 테트라에톡시시실란 208.33 g을 가하고, 60 ℃에서 8 시간 교반하였다. 반응액에 프로필렌글리콜모노프로필에테르 1500.00 g을 가한 후, 증발기로 1272 g (고형분 함유량 10 % 상당)으로 농축하고, 질산의 10 % 시클로헥사논 용액 150.00 g과 γ-부티로락톤 4950.00 g을 가하고 0.2마이크론 공경의 테프론제 필터로 여과하여 고형분 함유량 약 2 %의 막 형성용 조성물 2를 얻었다.
<실시예 3>
석영제 분리 플라스크 중에서, 10 % 수산화 테트라프로필암모늄 수용액100.00 g, 초순수 300.00 g, 에탄올 500.00 g 및 프로필렌글리콜모노프로필에테르500.00 g을 혼합하고, 계속해서 메틸트리메톡시실란 136.22 g과 테트라에톡시시실란 208.33 g을 가하고, 60 ℃에서 3 시간 교반하였다. 반응액에 시클로헥사논 1000.00 g을 가한 후, 증발기로 1390 g (고형분 함유량 10 % 상당)으로 농축하고, 질산의 10 % 시클로헥사논 용액 150.00 g과 γ-부티로락톤 5410.00 g을 가하고, 0.2 마이크론 공경의 테프론제 필터로 여과하여 고형분 함유량 약 2 %의 막 형성용 조성물 3을 얻었다.
[다른 실리카계 막을 위한 막 형성용 조성물의 조정]
석영제 분리 플라스크 중에서, 25 % 수산화 테트라에틸암모늄 수용액100.00 g, 초순수 200.00 g 및 에탄올 500.00 g을 혼합하고, 계속해서 메틸트리메톡시실란 81.73 g과 테트라메톡시실란 60.89 g을 가하고, 60 ℃에서 3 시간 교반하였다. 반응액에 프로필렌글리콜모노프로필에테르 1000.00 g을 가한 후, 증발기로 435 g (고형분 함유량 15 % 상당)으로 농축하고, 질산의 10 % 프로필렌글리콜모노프로필에테르 용액 100.00 g을 가하고, O.2 마이크론 공경의 테프론제 필터로 여과하여 고형분 함유량 약 12 %의 막 형성용 조성물을 얻었다.
[유기계 막을 위한 막 형성용 조성물의 조정]
온도계, 아르곤 가스 도입관, 교반 장치를 구비한 1000 ㎖ 3구 플라스크에 디에틸아민 150 ㎖, 디클로로비스트리페닐포스핀팔라듐 2.1 g, 요오드화구리 0.286 g, 1,2-디클로로에탄 600 ㎖, 4,4'-비스(2-요오도페녹시)벤조페논 185.72 g을 가하였다. 다음으로 4,4'-디에티닐디페닐에테르 65.48 g을 가하고, 50 ℃에서 20 시간 반응시켰다. 이 반응액을 아세트산 5 리터로 재침전을 2 회 반복한 후, 클로로포름에 녹여 초순수로 2 회 세정하고, 시클로헥산 5리터로 재침전하여 침전을 여과, 건조에 의해 중량 평균 분자량 35,000의 중합체 A를 얻었다. 이 중합체 A 12 g을 시클로헥사논 88 g에 용해하고, 0.2 마이크론 공경의 테프론제 필터로 여과하여 고형분 함유량 약 12 %의 유기막 형성용 조성물을 얻었다.
<비교예>
석영제 분리 플라스크 중에서, 초순수 50.00 g, 프로필렌글리콜모노에틸에테르 1200.00 g 및 말레산의 10 % 수용액 10.00 g을 혼합하고, 계속해서 메틸트리메톡시실란 136.22 g과 테트라에톡시시실란 208.33 g을 가하고, 60 ℃에서 5 시간 교반하였다. 반응액을 증발기로 1272 g (고형분 함유량 10 % 상당)으로 농축하고, 프로필렌글리콜모노프로필에테르 5090.00 g을 가하고, 0.2 마이크론 공경의 테프론제 필터로 여과하여 고형분 함유량 약 2 %의 비교용 막 형성용 조성물을 얻었다.
상술한 실시예 1 내지 3 및 비교예에 의해 얻어진 막 형성용 조성물에 대한 보존 안정성, 비유전율, 표면 거칠기 및 밀착성의 평가의 결과를 표 1에 나타내었다. 또한, 표 1의 참고예는 밀착층의 역할을 다할 수 있는 막을 개재하는 일 없이 다른 실리카계 막과 유기계 막을 직접 적층한 경우를 나타내고, 참고예의 보존 안정성, 비유전율 및 표면 거칠기의 결과는 다른 실리카계 막의 평가의 결과를 나타낸 것이다.
표 1로부터 분명한 바와 같이, 실시예 1 내지 3의 막 형성용 조성물을 다른 실리카계 막과 유기계 막의 사이에 형성한 적층체에 있어서, 밀착성이 향상되어 있는 것이 확인되었다. 즉, 본 발명의 막 형성용 조성물에 따르면, 유전율 특성, 보존 안정성 및 다른 실리카계 막 및 유기계 막과의 밀착성이 향상된 실리카계 막을 형성할 수 있다는 것을 알 수 있었다.
본 발명의 막 형성용 조성물에 의하면, (A)의 가수분해 축합물의 함유량이 5 중량% 미만이기 때문에 표면 거칠기가 큰 실리카계 막을 형성할 수가 있다. 그 때문에 예를 들면 본 발명의 막 형성용 조성물을 이용하여 형성되는 실리카계 막과 유기계 막을 적층시킬 경우, 실리카계 막과 유기계 막과의 계면으로서는 유기계 막이 실리카계 막 중으로 들어가는 앵커 효과에 의해, 밀착성을 향상시킬 수 있다. 또한, 예를 들면 본 발명의 막 형성용 조성물을 이용하여 형성되는 실리카계 막과 다른 실리카계 막을 적층시킬 경우, 실리카계 막과 다른 실리카계 막의 조성이 유사하기 때문에 밀착성을 향상시킬 수 있다. 즉, 본 발명의 막 형성용 조성물에 따르면 유기계 막 및 다른 실리카계 막의 각각에 대하여 밀착성을 갖는 실리카계 막을 얻을 수 있다.
또한, 본 발명의 막 형성용 조성물은 (B) 성분으로서, 유기 용매를 이용함으로써 저장 안정성이 우수한 막 형성용 조성물을 제공할 수 있다.
Claims (8)
- (A) 하기 화학식 1 또는 화학식 2로 표시되는 실란 화합물로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매 존재하에서 가수분해, 축합하여 얻어지는 가수분해 축합물과,(B) 환상 케톤 용매를 포함하고,상기 (A)의 가수분해 축합물의 함유량이 2 중량% 미만인 막 형성용 조성물.<화학식 1>RaSi(OR1)4-a<화학식 2>R2 b(R3O)3-bSi-(R6)d-Si(OR4)3-cR5 c식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이고, a는 0 내지 2의 정수이고,R2 내지 R5는 동일 또는 상이하고, 각각 1가의 유기기를 나타내고, b 및 c는 동일 또는 상이하고, O 내지 2의 수를 나타내고, R6은 산소 원자, 페닐렌기 또는 -(CH2)n-으로 표시되는 기 (여기서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
- 제1항에 있어서, 상기 알칼리 촉매가 알칼리 금속 수산화물, 암모니아, 알킬아민, 테트라알킬아민염으로부터 선택되는 1종 이상인 막 형성용 조성물.
- 제1항 또는 제2항에 있어서, 상기 환상 케톤 용매의 비점이 100 ℃ 내지 200 ℃인 막 형성용 조성물.
- 삭제
- 하기 화학식 1 또는 화학식 2로 표시되는 실란 화합물로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매, 물, 탄소수 3 이하의 알코올의 존재하에서 가수분해, 축합한 후, 환상 케톤 용매를 가하는 것을 포함하는, 제1항에 따른 막 형성용 조성물의 제조 방법.<화학식 1>RaSi(OR1)4-a<화학식 2>R2 b(R3O)3-bSi-(R6)d-Si(OR4)3-cR5 c식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이고, a는 0 내지 2의 정수이고,R2 내지 R5는 동일 또는 상이하고, 각각 1가의 유기기를 나타내고, b 및 c는 동일 또는 상이하고, 0 내지 2의 수를 나타내고, R6은 산소 원자, 페닐렌기 또는 -(CH2)n-으로 표시되는 기 (여기서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
- 하기 화학식 1 또는 화학식 2로 표시되는 실란 화합물로부터 선택되는 1종 이상의 실란 화합물을 알칼리 촉매, 물, 탄소수 3 이하의 알코올 및 환상 케톤 용매의 존재하에서 가수분해 축합하는 것을 포함하는, 제1항에 따른 막 형성용 조성물의 제조 방법.<화학식 1>RaSi(OR1)4-a<화학식 2>R2 b(R3O)3-bSi-(R6)d-Si(OR4)3-cR5 c식 중, R은 수소 원자, 불소 원자 또는 1가의 유기기이고, R1은 1가의 유기기이고, a는 0 내지 2의 정수이고,R2 내지 R5는 동일 또는 상이하고, 각각 1가의 유기기를 나타내고, b 및 c는 동일 또는 상이하고, 0 내지 2의 수를 나타내고, R6은 산소 원자, 페닐렌기 또는 -(CH2)n-로 표시되는 기 (여기서, n은 1 내지 6의 정수임)를 나타내고, d는 0 또는 1을 나타낸다.
- a) 실리카계 절연막의 위에 제1항에 따른 막 형성용 조성물을 도포하고, 건조하는 공정 및b) 상기 a)에서 얻어진 막 위에 또한 유기계 절연막을 형성하는 공정을 포함하는 것을 특징으로 하는, 절연막의 형성 방법.
- 제7항에 있어서, 실리카계 절연막이 도포형 폴리실록산 용액을 도포하여 가열하여 얻어지는 막 또는 CVD에 의해 얻어지는 막인 것을 특징으로 하는 절연막의 형성 방법.
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KR100620991B1 (ko) * | 2004-03-18 | 2006-09-08 | 엘지전자 주식회사 | 졸-겔 코팅용 조성물, 이의 제조방법 및 이를 이용하는표면 처리방법 |
JP4553693B2 (ja) * | 2004-11-19 | 2010-09-29 | 株式会社Adeka | ポリシロキサンの製造方法 |
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JP4616154B2 (ja) | 2005-11-14 | 2011-01-19 | 富士通株式会社 | 半導体装置の製造方法 |
DE602007000498D1 (de) * | 2006-04-11 | 2009-03-12 | Shinetsu Chemical Co | Siliziumhaltige, folienbildende Zusammensetzung, siliziumhaltige Folie, siliziumhaltiges, folientragendes Substrat und Strukturierungsverfahren |
US8197757B2 (en) * | 2006-07-07 | 2012-06-12 | Drexel University | Electrical insulation of devices with thin layers |
DE102011080884A1 (de) * | 2011-08-12 | 2013-02-14 | Siemens Aktiengesellschaft | Beschichtung mit hoher Koronabeständigkeit, sowie Herstellungsverfahren dazu |
KR102116834B1 (ko) | 2013-04-03 | 2020-05-29 | 주식회사 동진쎄미켐 | 비스-타입 실란화합물을 포함하는 코팅 조성물 |
KR101599953B1 (ko) | 2013-08-08 | 2016-03-04 | 제일모직 주식회사 | 실리카계 절연층 형성용 조성물, 실리카계 절연층 및 실리카계 절연층의 제조방법 |
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KR102411904B1 (ko) * | 2017-09-06 | 2022-06-21 | 한국전기연구원 | 알콜아민류 촉매를 이용한 졸-겔 실리카 입자 제조방법 및 실리카 입자가 코팅된 코팅기판 제조방법 |
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