TWI286155B - Composition for film formation, method of film formation, and silica-based film - Google Patents
Composition for film formation, method of film formation, and silica-based film Download PDFInfo
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- TWI286155B TWI286155B TW90108711A TW90108711A TWI286155B TW I286155 B TWI286155 B TW I286155B TW 90108711 A TW90108711 A TW 90108711A TW 90108711 A TW90108711 A TW 90108711A TW I286155 B TWI286155 B TW I286155B
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- Prior art keywords
- decane
- group
- bis
- compound
- film
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims description 34
- 230000015572 biosynthetic process Effects 0.000 title abstract description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title description 8
- 239000000377 silicon dioxide Substances 0.000 title 1
- -1 silane compound Chemical class 0.000 claims abstract description 107
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 230000007062 hydrolysis Effects 0.000 claims abstract description 28
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 3
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims abstract description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims abstract 4
- 150000004692 metal hydroxides Chemical class 0.000 claims abstract 4
- 239000000126 substance Substances 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 18
- 239000011248 coating agent Substances 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 15
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 11
- 239000010455 vermiculite Substances 0.000 claims description 11
- 235000019354 vermiculite Nutrition 0.000 claims description 11
- 229910052902 vermiculite Inorganic materials 0.000 claims description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229930004069 diterpene Natural products 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims 1
- JTLQBXZKPUPFFJ-UHFFFAOYSA-N [Bi].[BiH3] Chemical compound [Bi].[BiH3] JTLQBXZKPUPFFJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003636 chemical group Chemical group 0.000 claims 1
- 150000004141 diterpene derivatives Chemical class 0.000 claims 1
- 239000005078 molybdenum compound Substances 0.000 claims 1
- 150000002752 molybdenum compounds Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 238000009833 condensation Methods 0.000 abstract description 34
- 230000005494 condensation Effects 0.000 abstract description 34
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 229910000077 silane Inorganic materials 0.000 abstract 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 40
- 239000000047 product Substances 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 14
- 150000007514 bases Chemical class 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 150000002923 oximes Chemical class 0.000 description 10
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000052 vinegar Substances 0.000 description 9
- 235000021419 vinegar Nutrition 0.000 description 9
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- CGTNCTXIQDWSOL-UHFFFAOYSA-N 1-butoxydecane Chemical compound CCCCCCCCCCOCCCC CGTNCTXIQDWSOL-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003002 pH adjusting agent Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Chemical group 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000000149 argon plasma sintering Methods 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Chemical group CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical group CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical group CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000001354 calcination Methods 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
- 239000007822 coupling agent Substances 0.000 description 3
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical group CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229930003658 monoterpene Natural products 0.000 description 3
- 150000002773 monoterpene derivatives Chemical class 0.000 description 3
- 235000002577 monoterpenes Nutrition 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000005328 spin glass Effects 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OTGGHZUEAWMAAK-UHFFFAOYSA-N (1,1-dimethoxy-1-phenyldecan-2-yl)benzene Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)C1=CC=CC=C1)CCCCCCCC OTGGHZUEAWMAAK-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- WJMXTYZCTXTFJM-UHFFFAOYSA-N 1,1,1,2-tetraethoxydecane Chemical compound C(C)OC(C(OCC)(OCC)OCC)CCCCCCCC WJMXTYZCTXTFJM-UHFFFAOYSA-N 0.000 description 2
- ANBBCZAIOXDZPV-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methyldecane Chemical compound CC(C(OC)(OC)OC)CCCCCCCC ANBBCZAIOXDZPV-UHFFFAOYSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- LOLANUHFGPZTLQ-UHFFFAOYSA-N 1-ethoxydecane Chemical compound CCCCCCCCCCOCC LOLANUHFGPZTLQ-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
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical group CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical group CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- QCHXYWAOSIARJG-UHFFFAOYSA-N C(C)(C)C(C(OCCCC)(OCCCC)OCCCC)CCCCCCCC Chemical compound C(C)(C)C(C(OCCCC)(OCCCC)OCCCC)CCCCCCCC QCHXYWAOSIARJG-UHFFFAOYSA-N 0.000 description 2
- KIEVYECEKYDBHP-UHFFFAOYSA-N C(C)OC(CCCCCCCCCC(CCCCCCCCC)CCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC Chemical compound C(C)OC(CCCCCCCCCC(CCCCCCCCC)CCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC KIEVYECEKYDBHP-UHFFFAOYSA-N 0.000 description 2
- VXZILFOPZHPPGP-UHFFFAOYSA-N C(C)OC(CCCCCCCCCC1=CC(=CC=C1)CCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC Chemical compound C(C)OC(CCCCCCCCCC1=CC(=CC=C1)CCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC VXZILFOPZHPPGP-UHFFFAOYSA-N 0.000 description 2
- ZBSPXYUITZFELU-UHFFFAOYSA-N C(C)OC(OCC)C(CCCCCCCCC)CC(CCCCCCCCC)C(OCC)OCC Chemical compound C(C)OC(OCC)C(CCCCCCCCC)CC(CCCCCCCCC)C(OCC)OCC ZBSPXYUITZFELU-UHFFFAOYSA-N 0.000 description 2
- FAAXQBLJELOGKI-UHFFFAOYSA-N C(CCC)C(C(OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)CCCCCCCC Chemical group C(CCC)C(C(OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)CCCCCCCC FAAXQBLJELOGKI-UHFFFAOYSA-N 0.000 description 2
- FPYZFGNMCPBDBU-UHFFFAOYSA-N C(CCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CCC)C(C(OCC)(OCC)OCC)CCCCCCCC FPYZFGNMCPBDBU-UHFFFAOYSA-N 0.000 description 2
- JMBLCTYRAJLFSE-UHFFFAOYSA-N C(CCC)C(C(OCCC)(OCCC)OCCC)CCCCCCCC Chemical compound C(CCC)C(C(OCCC)(OCCC)OCCC)CCCCCCCC JMBLCTYRAJLFSE-UHFFFAOYSA-N 0.000 description 2
- AJVWYNUYXYIAKC-UHFFFAOYSA-N C(CCC)C(C(OCCCC)(OCCCC)OCCCC)CC Chemical compound C(CCC)C(C(OCCCC)(OCCCC)OCCCC)CC AJVWYNUYXYIAKC-UHFFFAOYSA-N 0.000 description 2
- NSCFHMBIYKTBLG-UHFFFAOYSA-N C(CCC)C(C(OCCCC)(OCCCC)OCCCC)CCCCCCCC Chemical group C(CCC)C(C(OCCCC)(OCCCC)OCCCC)CCCCCCCC NSCFHMBIYKTBLG-UHFFFAOYSA-N 0.000 description 2
- JSGRIFNBTXDZQU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC JSGRIFNBTXDZQU-UHFFFAOYSA-N 0.000 description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- XCRZAIPPBHIKOR-UHFFFAOYSA-N prop-2-enyl 4-amino-3-fluorobenzoate Chemical compound NC1=CC=C(C(=O)OCC=C)C=C1F XCRZAIPPBHIKOR-UHFFFAOYSA-N 0.000 description 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004901 spalling Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
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Classifications
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- H—ELECTRICITY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- 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
- C08G77/50—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 by carbon linkages
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- 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
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- 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
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- 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
- H01L21/02214—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 the compound comprising silicon and oxygen
- H01L21/02216—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 the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/00—Stock material or miscellaneous articles
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Description
1286155 五、發明說明(1) 曰本發明是關於一種薄膜成形用組成物。特別是,本發明 =關,一種薄膜成形用組成物,當將其用於製造半導體元 之類中的隔層絕緣膜材料時,可以得到在pcT(壓力鍋試 B之後的介電常數特性、在pCT之後的CMp阻抗力(化學機 g研磨)、以及在PCT之後對基板的黏著性優良之矽石基 八=^疋CVD方法之真空方法所形成之矽石(Si02)膜,迄 =被用作為半導體元件和其他元件中的隔層絕緣膜。 稱Α f &種包含四烷氧基矽烷水解產物作為主要成分且 冉為SOG(自旋玻璃)薄膜之絕緣塗層薄膜,已被用於形成 邑緣膜的目的。再者,纟半導體元件之類趨於較
At,結果’已發展出—種稱為有機S0G薄膜之隔 含聚有機梦氧烧作為主要成分,而且具有 低的介電常數。 〃 ’ 展H!!是在半導體元件之類巾乡層組成的整合度之進 在導體之間較佳的電絕緣變得必要,並且因此,具 乂 ^介電常數且優良抗斷裂強度之隔層絕緣膜變得理相。 ,:有低介電常數之材::,料,為含有:在氨的存:下 所:夕烧與烧氧基侧部分水解之基本編 於2々*丨,支粒!!參見几4一5一26304 5和;1^-5一315319(用 ;,yp—^ 一詞是指”未審查公開日本專利申請案,·) ”在氰的存在下,將聚烧氧基⑪燒的基本水解產物縮 第5頁 C:\2D-OODE\90-07\90108711.ptd 1286155 五、發明說明(2) 合所得到的塗層流體(參見jp —A-ι 1 -340 2 1 9和JPn j 340 220 )之混合物的組成物。然而,經由這些方法所❹ 的材料並不適用於工業製造,因為該反應產物的不穩=, 質,以及由此所得到的薄膜具有相當不均勻的性質,, 在PCT之後的介電常數特性、在PCT之後的CMP阻抗力、ρ疋 及在PCT之後對基板的黏著性。 u 發明之概诚 本發明的一個目的是提供一種薄膜成形用組成物,其 除了上述的問題。特別是,該目的是提供一種薄膜成形用 組成物,當將其用於製造半導體元件之類時,可以得到在 PCT之後的介電常數特性,在PCT之後的cMp阻抗力,以及 在PCT之後對基板的黏著性優良之隔層絕緣膜。本發明的 另一個目的是提供從該組成物所得到之矽石基膜。 本發明提供一種薄膜成形用組成物,其包含: 德(二在Λ以Λ至/ 一個選自四烷基氫氧化銨、脂 Μ二έ J1虱乳化物(在下文中參照為”特殊鹼性化合物 f ι化口物的存在下,將至少一個選自下列 化學式(1)所示化合物 ^ ^ 。物(在下文中參照為”化合物(1)")、下
列化学式(2 )所示化合物f Α 了 i,A 下别π與4 r q、 下文中參照為"化合物(2 ) π )和 下列化學式(3 )所示化合妨^ + 所組成的族群之石夕烷化合Γ文中參照為π化合物(3)π) 縮合產物; 水解並縮合,所得到的水解和
RaSi(〇Ri )4_a 其中R表示氫原子、氟溽子々(1) 氣原子或早價有機基;R1表示單價有 C:\2D-CODE\90-07\90108711.ptd $ 6頁
(2 1286155 五、發明說明(3) 機基;且a為1或2之整數 Si(OR2)4 其中R2表示單價有機基; R3b(R4〇VbSi -(R7)d-Si(0R5)3、cR6 其中㈣可能是相同或不同,並且分別 乂和c可能是相同或不同,並且分別為。至2的數目有ϋ 不氧原子、伸苯基、或是由- 表 1 5 R ^ ^ ^ 次疋由所不官能基,其中η 1至6的整數,·且d為0或1 ;以及 馮 (B)有機溶劑。 本發明進一步提供一種薄膜成形用方法,其包含將上、十、 :薄膜成形用組成物應用^基板上,然後加熱該所得塗迷 本發明更進一步提供一種矽石基膜, 用方法所得到的。 4辟勝成形 發明之詳細說明 本發明中水解和縮合的產物(A),是指至少一個選自化 。物(1 )至(3 )所組成的族群之化合物的水解產物,和該 解產物的縮合物之混合物;或是指該水解產物或縮合=。 在成分(A)的水解產物中,並不需要將構成成分(人)之 合物(1)至(3)中所包括的所有R1〇一、R2〇—、R4〇—和『〇—官能 基水解。例如,該水解產物可能是一個只水解這些官能ς
其中之一、或是水解其二或多個官能基之產物,或者可心 是這些產物的混合物。 I 在成分(Α)中的縮合物,是指從構成成分(Α)之化合物 第7頁 \\312\2d-code\90-07\90108711.ptd 1286155
(1 )至(3 )之水解產物 的矽烷醇基縮合來來占/^的產物,係藉由將該水解產物 f不而要將所有的石夕烷醇基進行縮合作用。換言之,本文 中所用之,,縮合”一句θ 4t 叮难口忭用硖口爻,本文 彳八Μ Θ、P> _ t ^ Λ 疋扣一種觀念,例如,其包括將少部 伤的矽烷醇基縮合之始入 混合物。 t縮合物,以及不同縮合度之縮合物的 水解和縮合的吝物」 該$解和縮合的產物(A ),是在特殊鹼性化合物的存在 下:至J y個選自化合物(1)至(3 )所組成的族群之矽烷 化e物水解並縮合所得到的。 化合物(1 ): j化學式(1)中R和1^1所示單價有機基的例子,包括烷基 、方基、烯丙基和縮水甘油基。在化學式(丨)中,R較佳是 單價有機基,更佳是烷基或苯基。 该烷基較佳具有1至5個碳原子,並且其例子包括甲基、 乙基、、丙基和丁基。這些烷基可能是直鏈或分支鏈,並且 可能為其中一或多個氫原子被例如氟原子所取代之烷基。 在化學式(1)中,芳基的例子包括··苯基、萘基、甲基 苯基、乙基苯基、氯苯基、溴苯基和氟苯基。 化學式(1 )所示化合物的例子包括··三甲氧基石夕烧、 二乙乳基石夕燒、三-正丙氧基石夕烧、三-異丙氧基石夕烧、 三-正丁氧基矽烷、三-二級丁氧基矽烷、三_三級丁氧基 矽統、三苯氧基矽烷、氟三甲氧基矽烧、氟三乙氧基矽 烧、氟三~正丙氧基矽烷、氟三_異丙氧基矽烷、氟三一正
C:\2D-CQDE\90-07\90108711.ptd 第8頁 1286155 五、發明說明(5) 、丁氧基矽烷、氟三—二級丁氧基矽烷、氟三—三級丁氧基矽 烷、和氟二笨氧基矽烷;甲基三曱氧基矽烷、曱基三乙氧 基矽烷、甲基三—正丙氧基矽烷、甲基三-異丙氧基矽烷、 甲-基二-正丁氧基矽烷、甲基三—二級丁氧基矽烷、甲基三 -三級丁氧^基矽烷、甲基三苯氧基矽烷、乙基三曱氧基矽 、元 乙基一乙氧基石夕烧、乙基三-正丙氧基石夕燒、乙基三一 異丙氧基石夕烧、乙基三—正丁氧基矽烷、乙基三—二級丁氡 基矽烷二乙基三-三級丁氧基矽烷、乙基三苯氧基矽烷、 乙稀基三曱氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三一 正丙氧基石夕烷、乙烯基三-異丙氧基矽烷、乙烯基三-正丁 ,基矽烷、乙烯基三-二級丁氧基矽烷、乙烯基三—三級丁 氧基石夕烧、乙烯基三苯氧基矽烷、正丙基三甲氧基石夕烧、 ^丙基二乙氧基矽烷、正丙基三-正丙氧基矽烷、正丙基 三-異丙氧基矽烷、正丙基三-正丁氧基矽烷、正丙基三一 二級丁氧基矽烷、正丙基三-三級丁氧基矽烷、正丙基三 苯氧基石夕烧、異丙基三甲氧基矽烷、異丙基三乙氧基石夕院 、異丙基三-正丙氧基矽烷、異丙基三—異丙氧基矽烷、異 丙基三-正丁氧基矽烷、異丙基三—二級丁氧基矽烷、異/丙 基三-三級丁氧基矽烷、異丙基三苯氧基矽烷、正丁基三 甲氧基石夕烧、正丁基三乙氧基矽烷、正丁基三〜正丙氧基 矽烷、正:基三-異丙氧基矽烷、正丁基三-正丁氧基石夕^ 、正丁基三-二級丁氧基矽烷、正丁基三—三級丁氧基矽= 、正丁基三苯氧基矽烷、二級丁基三曱氧基矽梡、二級^ 基三乙氧基矽烷、二級丁基三—正丙氧基矽烷、二級丁美
C:\2D-C0DE\90-07\90108711.ptd 第9頁 1286155 五、發明說明(6) 三-異丙氧基矽烷、二級丁基三-正丁氧基矽烷、二級丁基 三-二級丁氧基矽烷、二級丁基三-三級丁氧基矽烷、二級 丁基三苯氧基矽烷、三級丁基三甲氧基矽烷、三級丁基三 乙氧基矽烷、三級丁基三_正丙氧基矽烷、三級丁基三-異 丙氧基矽烷、三級丁基三-正丁氧基矽烷、三級丁基三-二 級丁氧基矽烷、三級丁基三-三級丁氧基矽烷、三級丁基 三苯氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、 苯基三-正丙氧基矽烷、苯基三-異丙氧基矽烷、苯基三-正丁氧基矽烷、苯基三-二級丁氧基矽烷、苯基三-三級丁 氧基矽烷、苯基三苯氧基矽烷、7 -氨丙基三曱氧基矽烷 、7-氨丙基三乙氧基石夕烧、7 -縮水甘油氧丙基三甲氧基 石夕烧、縮水甘油氧丙基三乙氧基石夕烧、7 -三氟丙基三 甲氧基矽烷、和r_三氟丙基三乙氧基矽烷;以及 二曱基二甲氧基矽烷、二甲基二乙氧基矽烷、二甲基二 -正丙氧基砍烧、二曱基二-異丙氧基碎院、二甲基二-正 丁氧基矽烷、二甲基二-二級丁氧基矽烷、二甲基二-三級 丁氧基矽烷、二曱基二苯氧基矽烷、二乙基二甲氧基矽烷 、二乙基二乙氧基矽烷、二乙基二-正丙氧基矽烷、二乙 基二-異丙氧基石夕烧、二乙基二-正丁氧基碎烧、二乙基二 -二級丁氧基矽烷、二乙基二-三級丁氧基矽烷、二乙基二 苯氧基矽烷、二-正丙基二甲氧基矽烷、二-正丙基二乙氧 基矽烷、二-正丙基二-正丙氧基矽烷、二_正丙基二-異丙 氧基矽烷、二-正丙基二-正丁氧基矽烷、二-正丙基二-二 級丁氧基矽烷、二-正丙基二-三級丁氧基矽烷、二-正丙
C:\2D-CQDE\90-07\90108711.ptd 第10頁 1286155 五、發明說明(7) 基二苯氧基矽烷、二異丙基二甲氧基矽烷、二異丙基二乙 氧基石夕烧、二異丙基二-正丙氧基石夕烧、二異丙基二-異丙 氧基矽烷、二異丙基二-正丁氧基矽烷、二異丙基二-二級 丁氧基矽烷、二異丙基二-三級丁氧基矽烷、二異丙基二 苯氧基矽烷、二-正丁基二甲氧基矽烷、二-正丁基二乙氧 基石夕炫、二-正丁基二-正丙氧基石夕烧、二-正丁基二-異丙 氧基矽烷、二-正丁基二-正丁氧基矽烷、二-正丁基二-二 級丁氧基矽烷、二-正丁基二-三級丁氧基矽烷、二-正丁 基二苯氧基矽烷、二-二級丁基二甲氧基矽烷、二-二級丁 基二乙氧基矽烷、二-二級丁基二-正丙氧基矽烷、二-二 級丁基二-異丙氧基矽烷、二-二級丁基二-正丁氧基矽烷 、二-二級丁基二-二級丁氧基矽烷、二-二級丁基二-三級 丁氧基矽烷、二-二級丁基二苯氧基矽烷、二-三級丁基二 甲氧基矽烷、二-三級丁基二乙氧基矽烷、二-三級丁基二 -正丙氧基碎烧、二-三級丁基二-異丙氧基秒烧、二-三級 丁基二-正丁氧基矽烷、二-三級丁基二-二級丁氧基矽烷 、二-三級丁基二-三級丁氧基碎烧、二-三級丁基二苯氧 基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷、二 苯基二-正丙氧基矽烷、二苯基二-異丙氧基矽烷、二苯基 二-正丁氧基矽烷、二苯基二-二級丁氧基矽烷、二苯基二 -三級丁氧基矽烷、二苯基二苯氧基矽烷、和二乙烯基三 曱氧基矽烷。 化合物(1)的較佳例子包括: 曱基三曱氧基矽烷、甲基三乙氧基矽烷、甲基三-正丙
C:\2D-CQDE\90-07\90108711.ptd 第11頁 1286155 五、發明說明(8) 氧基^烷、甲基三-異丙氧基矽烷、乙基三甲氧基矽烷、 ^基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧 =矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、二甲基 二甲氧基矽烷、二甲基二乙氧基矽烷、二乙基二甲氧基矽 二?基二乙氧基矽烷、二苯基二甲氧基矽烷、和二苯 基一乙氧基石夕烧。 可以將這些化合物單獨使用,或者是其二或多個組合使 用。 化合物(2) ·· 在化學式(2)中R2所示單價有機基的例子,包括如上面 化學式(1)所列舉的相同單價有機基。 化學式(2)所示化合物的例子包括:四甲氧基矽俨、 乙氧基矽烷、四-正丙氧基矽烷、四_異丙氧基矽烷'四— 正丁氧基矽烷、四-二級丁氧基矽烷、四_三級丁 、和四苯氧基矽烷。 乳暴砂现 化合物(3 ): 在化學式(3)中R3至R6所示單價有機基的例子, 面化學式(1)所列舉的相同單價有機基。 i枯如上 化學式(3)所示化合物,其中R7為氧原子的例子 六甲氧基二石夕氧烧、六乙氧基二石夕氧烧、六苯氧基=石夕氧 烧、 、 1,1,1,3, 3-五甲氧基- 3-甲基二石夕氧烧、 1,1,1,3,3-五乙乳基-3-甲基二石夕氧烧、 1,1,1,3, 3-五苯氧基-3-甲基二矽氧烧、 C:\2D-CODE\90-07\90108711.ptd $ 12頁 1286155 五、發明說明(9) 1,1,1,3,3 -五曱氧基-3-乙基二矽氧烷、 1,1,1,3,3 -五乙氧基-3-乙基二石夕氧烧、 1,1,1,3,3 -五苯氧基-3-乙基二矽氧烷、 1,1,1,3, 3 -五曱氧基-3-苯基二矽氧烷、 1,1,1,3,3 -五乙氧基-3 -苯基二矽氧烷、 1,1,1,3,3 -五苯氧基-3 -苯基二矽氧烷、 1,1,3, 3-四曱氧基-1,3 -二甲基二矽氧烷、 1,1,3, 3-四乙氧基_1,3 -二曱基二矽氧烷、 1,1,3, 3 -四苯氧基-1,3 -二甲基二矽氧烷、 1,1,3, 3 -四曱氧基-1,3 -二乙基二矽氧烷、 1,1,3, 3 -四乙氧基-1,3 -二乙基二矽氧烷、 1,1,3, 3 -四苯氧基-1,3-二乙基二矽氧烷、 1,1,3, 3 -四甲氧基-1,3 -二苯基二矽氧烷、 1,1,3, 3 -四乙氧基-1,3 -二苯基二矽氧烷、 1,1,3, 3 -四苯氧基-1,3 -二苯基二矽氧烷、 1,1,3 -三甲氧基-1,3, 3 -三甲基二矽氧烷、 1,1,3-三乙氧基-1,3, 3-三甲基二矽氧烷、 1,1,3 -三苯氧基-1,3, 3-三甲基二矽氧烷、 1,1,3-三甲氧基-1,3, 3-三乙基二矽氧烷、 1,1,3 -三乙氧基-1,3, 3 -三乙基二矽氧烷、 1,1,3 -三苯氧基-1,3,3 -三乙基二矽氧烷、 1,1,3-三甲氧基-1,3, 3-三苯基二矽氧烷、 1,1,3 -三乙氧基-1,3, 3 -三苯基二矽氧烷、 1,1,3 -三苯氧基-1,3, 3 -三苯基二矽氧烷、
C:\2D-CODE\90-07\90108711.ptd 第13頁 1286155 五、發明說明(ίο) 1,3 -二曱氧基-1,1,3, 3 -四曱基二矽氧烷 1,3 -二乙氧基-1,1,3, 3 -四甲基二矽氧烷 1.3 -二苯氧基-1,1,3,3 -四甲基二石夕氧烧 1,3 -二曱氧基-1,1,3,3-四乙基二石夕氧烧 1.3 -二乙氧基-1,1,3,3 -四乙基二砍氧烧 1.3 -二苯氧基-1,1,3, 3 -四乙基二矽氧烷 1,3 -二甲氧基-1,1,3,3_四苯基二矽氧烷 和 和 1.3 -二乙氧基-1,1,3, 3 -四苯基二矽氧烷 1,3-二苯氧基-1,1,3,3-四苯基二矽氧烷 矽氧烷、六乙氧基二矽 這些化合物較佳的是六甲氧基 氧烷、 1,1,3, 3 -四甲氧基-1,3 -二甲基二矽氧烷 1,1,3, 3 -四乙氧基-1,3 -二曱基二矽氧烷 1,1,3, 3 -四甲氧基-1,3 -二苯基二矽氧烷 1.3 -二甲氧基-1,1,3, 3-四甲基二矽氧烷 1.3 -二乙氧基-1,1,3, 3 -四甲基二矽氧烷 1.3 -二曱氧基-1,1,3,3_四苯基二砍氧烧 1,3 -二乙氧基-1,1,3, 3 -四苯基二矽氧烷 化學式(3 )所示化合物,其中d為0的例子包括:六甲氧 基二矽烷、六乙氧基二矽烷、 1,1,1,2, 2-五曱氧基-2-甲基 1,1,1,2, 2-五乙氧基-2-甲基 1,1,1,2, 2-五苯氧基-2-甲基 1,1,1,2, 2-五曱氧基-2-乙基 六苯氧基二矽烷 二矽烷、 二矽烷、 二矽烷、 二矽烷、
C:\2D-CODE\90-07\90108711.ptd 第14頁 1286155 五、發明說明(11) 1,1,1,2,2 -五乙氧基-2-乙基二矽烷、 1,1,1,2,2 -五苯氧基-2-乙基二矽烷、 1,1,1,2, 2-五甲氧基-2 -苯基二矽烷、 1,1,1,2,2 -五乙氧基-2 -苯基二矽烷、 1,1,1,2,2 -五苯氧基-2-苯基二矽烷、 1,1,2, 2-四甲氧基-1,2-二甲基二矽烷、 1,1,2, 2-四乙氧基-1,2-二曱基二矽烷、 1,1,2, 2 -四苯氧基-1,2-二甲基二矽烷、 1,1,2, 2 -四曱氧基-1,2 -二乙基二矽烷、 1,1,2, 2-四乙氧基-1,2 -二乙基二矽烷、 1,1,2, 2 -四苯氧基_ 1,2 -二乙基二矽烷、 、1,1,2, 2-四曱氧基-1,2 -二苯基二矽烷、 1,1,2, 2-四乙氧基-1,2-二苯基二矽烷、 1,1,2, 2-四苯氧基-1,2 -二苯基二矽烷、 1,1,2 -三曱氧基-1,2, 2-三甲基二矽烷、 1,1,2-三乙氧基-1,2, 2 -三甲基二矽烷、 1,1,2-三苯氧基-1,2, 2-三甲基二矽烷、 1,1,2-三甲氧基-1,2, 2 -三乙基二矽烷、 1,1,2 -三乙氧基-1,2, 2 -三乙基二矽烷、 1,1,2 -三苯氧基-1,2, 2 -三乙基二矽烷、 1,1,2 -三甲氧基-1,2,2-三苯基二矽烷、 1,1,2 -三乙氧基-1,2, 2 -三苯基二矽烷、 1,1,2 -三苯氧基-1,2, 2 -三苯基二矽烷、 1,2 -二甲氧基-1,1,2, 2-四甲基二矽烷、
C:\2D-CODE\90-07\90108711.ptd 第15頁 1286155 五、發明說明(12) 1,2-二乙氧基-1,1,2, 2-四甲基」 1,2 - 一本乳基-1,1,2,2 -四曱基· 1,2-一甲氧基-1,1,2,2-四乙基· 1,2-二乙氧基-1,1,2, 2-四乙基二 1,2-二苯氧基-1,1,2, 2-四乙基^ 1,2-二甲氧基-1,1,2, 2 -四苯基二 1,2 -二乙氧基-1,1,2,2 -四苯基二 1,2-二苯氧基-1,1,2, 2-四苯基二 這些化合物較佳的是六曱氧基 烷、 1,1,2, 2-四甲氧基-1,2-二甲基二 1,1,2,2 -四乙氧基-1,2 -二甲基、 1,1,2, 2-四甲氧基-1,2 -二苯基二 1,2-^一甲氧基-1,1,2,2-四甲基~ 1,2-《—乙氧基-1,1,2,2-四曱基:1,2 -二曱氧基-1,1,2, 2 -四笨基二 1,2 -二乙氧基-1,1,2, 2 -四苯基二 化學式(3)所示化合物’其中R7為」“a所示官能基的 例子包括:雙(三曱氧基矽烷基)甲烷、雙(三乙氧基矽烷 基)曱烷、 石夕垸 石夕燒 矽燒, 矽烷, 矽烷、 矽燒、 矽烷、 矽燒c 矽烷、 矽烷、 矽燒、 矽烷、 矽烷、 矽烷、 矽烷 和 六乙氧基 矽 和 雙(三-正丙氧基矽烷基)甲烷、 雙(三異丙氧基矽烷基)曱烷、 雙(三-正丁氧基矽烧基)甲烧、 雙(三-二級丁氧基矽烷基)曱烷、
第16頁 1286155 五、發明說明(13) ^ ' 雙(三-三級丁氧基矽烷基)曱烷、 1,2 -雙(三甲氧基矽烷基)乙烷、 1,2_雙(三乙氧基矽烷基)乙烷、 1,2_雙(三-正丙氧基矽烷基)乙烷、 1,2-雙(三異丙氧基矽烷基)乙烷、 1,2_雙(三-正丁氧基矽烷基)乙烷、 1,2_雙(三-二級丁氧基矽烷基)乙烷、 1,2-雙(三-三級丁氧基矽烷基)乙烷、 1 -(一甲氧基曱基矽烷基)一1 一(三甲氧基矽烷基)曱烷、
1 -(二乙氧基甲基矽烷基)-1一(三乙氧基矽烷基)甲烷、 1 -(二-正丙氧基曱基矽烷基卜卜(三—正丙氧基矽烷基)曱 烧、 1_( 一異丙氧基甲基石夕燒基)-1 -(三異丙氧基石夕烧基)甲烧 卜(二—正丁氧基甲基矽烷基)-卜(三-正丁氧基矽烷基)甲 烷、 卜(二-二級丁氧基曱基矽烷基)_卜(三-二級丁氧基矽烷基 )甲烷、 1 一(一-二級丁氧基曱基石夕烧基)-1-(三-三級丁氧基石夕烧基 )甲烧、 1 一(二曱氧基甲基矽烷基)-2-(三曱氧基矽烷基)乙烷、 1 -(二乙氧基甲基矽烷基)—2_(三乙氧基矽烷基)乙烷、 卜(二-正丙氧基甲基矽烷基)_2-(三-正丙氧基矽烷基)乙 烷、
C:\2D-CQDE\90-07\90108711.ptd 第17頁 1286155 、發明說明(14) (一異丙氧基甲基矽烷基)—2_(三異丙氧基矽烷基)乙烷 正丁氧基曱基矽烷基)一2 -(三-正丁氧基矽烷基)乙 燒' 1 〜(二' )乙燒、 1 〜(二' )乙烷、 雙(二甲氧基甲基矽烷基)甲烷、 雙(二乙氧基甲基矽烷基)甲烷、 雙(二-正丙氧基甲基矽烷基)甲烷、 雙(二異丙氧基甲基矽烷基)甲烷、 雙(二-正丁氧基甲基矽烷基)甲烷、 雙(二〜二級丁氧基甲基矽烷基)甲烷 雙(二-三級丁氧基曱基矽烷基)甲烷 級丁氧基甲基石夕烧基)一2一( 級丁氧基甲基石夕烧基)一2一( 、級丁氧基矽烷基 級 氧基矽烷基 « 1,2-雙 1,2-雙 1,2-雙 2-雙 2-雙 2-雙 2-雙 2-雙 2-雙 (二曱氧基曱基矽烷基)乙烷、 (二乙氧基曱基矽烷基)乙烷、 (二—正丙氧基曱基矽烷基)乙烷、 (二異丙氧基甲基矽烷基)乙烷、 (二-正丁氧基甲基矽烷基)乙烷、 (二-二級丁氧基曱基矽烷基)乙烷 / 級丁氧基曱基矽烷基)乙烷 # 二 甲氧基矽烷基)苯 乙氧基矽烷基)苯
C:\2D-CQDE\90-07\90108711.ptd 第18頁 1286155 五、發明說明(15) 1.2 -雙(三-正丙氧基矽烷基)苯、 1,2-雙(三異丙氧基矽烷基)苯、 1,2 -雙(三-正丁氧基矽烷基)苯、 1.2 -雙(三-二級丁氧基梦烧基)苯 1.2 -雙(三-三級丁氧基矽烷基)苯 1,3-雙(三甲氧基矽烷基)苯、 1,3-雙(三乙氧基矽烷基)苯、 1.3 -雙(三-正丙氧基石夕烧基)苯、 1,3-雙(三異丙氧基矽烷基)苯、 « 1.3 -雙(三-正丁氧基矽烷基)苯、 1,3 -雙(三-二級丁氧基碎烧基)苯 1,3 -雙(三-三級丁氧基矽烷基)苯 1,4-雙(三甲氧基矽烷基)苯、 1,4-雙(三乙氧基矽烷基)笨、 1,4 -雙(三-正丙氧基矽烷基)苯、 1,4_雙(三異丙氧基矽烷基)苯、 4-雙(三-二級丁氧基矽烷基)苯、和 4 -雙(三-三級丁氧基碎烧基)苯。 這些化合物較佳的是雙(三甲氧基矽烷基)甲烷、 雙(三乙氧基矽烷基)曱烷、 1,2_雙(三曱氧基石夕烧基)乙院、 1,2 -雙(三乙氧基石夕烧基)乙烧、 卜(二曱氧基甲基矽烷基)- :1 -(三曱氧基矽烷基)甲烷 1.4 -雙(三-正丁氧基矽烷基)苯、 1, 1,
C:\2D-CQDE\90-07\90108711.ptd 第19頁 1286155
卜d甲,ί甲基矽烷基)一卜(三乙氧基矽烷基)甲烷、 7,土甲基矽烷基)一2—(三甲氧基矽烷基)乙烷、 雔Γ-甲%基豈甲基矽烷基)—2—(三乙氧基矽烷基)乙烷、 又(一曱氧基曱基矽烷基)甲烷、 雙(二乙氧基甲基矽烷基)甲烷、 1,2雙(二甲氧基甲基矽烷基)乙烷、 1,2-雙(二乙氧基甲基矽烷基)乙烷、 1,2-雙(三甲氧基矽烷基)苯、 1,2 -雙(三乙氧基矽烷基)苯、
1,3-雙(三甲氧基矽烷基)苯、 1,3-雙(三乙氧基矽烷基)苯、 1,4-雙(三甲氧基矽烷基)苯、和 1,4 -雙(三乙氧基矽烷基)苯。 在本發明中,可以將上述化合物(丨)、(2 )和(3 )單獨使 用,或者是其二或多個組合使用來構成成分 當將至少一個選自化合物(1 )至(3)所組成的族群之矽烷 化合物水解並縮合時,每莫耳之至少一個選自化合物(1) 至(3)之化合物中,所使用水的量較佳是多於2〇 11]〇1至15〇 mol更佳疋多於20 mol至130 mol。如果所加入水的量為 2 0 mo 1或更少’則所得組成物得到具有不良抗斷裂強度之 塗層薄膜。另一方面,如果所加入水的量大於15〇 m〇1, 則在水解和縮合反應期間會發生聚合物沉澱或凝膠。 將至少一個選自化合物(丨)至(3)所組成的族群之石夕院化 合物至該反應混合物的加成,可以集體操作、或是連續或
1286155 五 發明說明(17) 斷續地操作。在連續或斷續地加入該至少一個選自化合 (1 )至(3)所組成的族群之矽烧化合物的例子 間較佳是從5分鐘至12小時。 月 用於本發明之水解和縮合的產物(A )之製造的特色為· 在水解並縮合至少一個選自化合物(1)至(3)所組成的‘族群 之矽烷化合物中,使用特殊鹼性化合物。 、 藉由使用特殊鹼性化合物,可以得到具有低介電常數、 高彈性模數、且對基板優良黏著性之矽石基膜。 、 一可用於本發明之特殊驗性化合物的例子包括:四烧美5 氧化銨,像是四甲基氫氧化銨、四乙基氫氧化銨、二二二 氫氧化銨和四丁基氫氧化銨;脂環族有機胺,像是呢。定土 (Piperidine)、卜甲基哌啶、2-甲基哌啶、3一甲基旅$、 4-甲基哌啶、哌畊(piperazine)、卜甲基哌啡、2-甲基哌 呀、1,4-二曱基哌畊、咄咯啶(pyrrol idine)、卜甲基1 略啶、二吖雙環辛烷((1丨32&13丨〇7(:1〇〇(^3116)、二叮雙環壬 烧、二吖雙環十一烯、2 -咄唑啉(pyraz〇i ine ) 、3 —吼略 琳(pyrroline)、和说^(quinuclidine);以及金屬氯氧 化物,像是氫氧化鈉、氫氧化鉀、氫氧化鋰和氫氧化絶。 從對基板之矽石基膜的黏著性之觀點,這些化合物較佳的 是··四甲基氫氧化銨、四乙基氫氧化銨、四丙基氫^化錄 、四丁基氫氧化銨、哌啶、1 -甲基哌啶、哌畊、甲基呢 °井、1,4-二甲基哌啡、吼咯啶、1 -甲基咄咯啶、二叮^環 辛燒、二吖雙環壬烷、二吖雙環十一烯、氫氧化鈉、^ 化鉀和氫氧化鋰。
C:\2D-CGDE\90-07\901087Il.ptd 1286155 五、發明說明(18) 可以將這些特殊鹼性化合物單獨使用,或者是農二 個組合使用。 一驭夕 每莫耳之包含於化合物(][)至之以〇_、R2〇〜、和 R50-官能基的總量,所使用特殊鹼性化合物的量通常曰σ 0 0 0 0 1至10 mol,較佳是0 0 0 0 05至5 m〇1,最佳是『至 0· 5 mo 1。只要所使用特殊鹼性化合物的量是在該範圍之 内’則在反應期間不易發生聚合物沉澱或凝膠。 之 因此所得到水解和縮合的產物(A )之迴轉半徑, 由GPC (折射率、黏度、或光散射)方法所測定的迴^ : 徑而言,較佳是5至50 nra,更佳是8至4〇 nm,最佳 2 0 nm。當該水解和縮合的產物具有5至5〇 nm的迴7^
,則該組成物可以得到介電常數、彈性模數、且 L 度特別優良之矽石基膜。 y m句句 因此所得到水解和縮合的產物(A)具有非微粒 ,並因此對基板具有優良的適用性。可以經由、% 二=顯微鏡(TEM)檢定來確認該水解和縮合的產物㊁= 在成分(A)中,就完全水解和縮合的產物而言 化合物所衍生水解和縮合的產物之比例如 個別 化合物(1)至⑺所衍生水解和縮合的產 她,於所有從 物(2)所衍生水解和縮合的產物之含 〜&,從化合 75 % ,較佳是以重量計10至70 % ,更"^曰疋以重旦量計5至 7 0 % 。基於所有從化合物(丨)至(3 )所衍疋 里汁1 5至 產物之總合,從化合物(1)和/或化合 =解和縮合.的 奶所衍生水解和 C:\2D-CQDE\90-07\90108711.ptd 第22頁 1286155 五、發明說明(19) 的產物之含Ϊ通常是以重量計95至託% ,較佳是以 "里计9 0至3 0 % ,更佳是以重量計8 5至3 〇 % 。基於所有 從$合物(1 ) f ( 3 )所衍生水解和縮合的產物之總合,當從 :口物丄2)所何生水解和縮合的產物之含量為以重量計5至 八則所得塗層薄膜具有高的彈性模數以及極低的 介電常數。 从本ί I所用之丨$全水解和縮合的產物丨丨—詞是指一種產 1 忐基已被水解為^⑽基,並且完全縮合形成 矽氧烷結構。 二佳日的八成/(Α)為至少一個化合物⑴和至少-個化合物 的^合物之水解和縮合的產物,因為該成分(Α)賦予將 付到的組成物較佳的儲存穩定度。 J 5水f和縮合的產物(A)中,是在特殊鹼性化合物 之二至少7個選自化合物(1)至(3)所組成的族群 ΐ t σ ±水解並縮合,使得所得水解和縮合的產物較
有:轉半徑5至50 nm。調整該所得組 或更低較佳。 P I pH調整用技術之例子包括: ⑴加入pH調節劑; —在吊壓或減壓下,將特殊鹼性化合物從該組成物中 瘵餾出; ()將k疋氮氣或氬氣之氣泡吹入該組, 特殊鹼性化合物從該組成物移去; 因此將
1286155 五、發明說明(20) (4 )以離子交換樹脂將特殊驗性化合物從該組成物移 去,·以及 (5 )以卒取或洗滌將特殊驗性化合物從該組成物移去。 這些技術可以單獨使用,或者是其二或多個組合使用。 pH調節劑的例子包括無機酸和有機酸。 無機自文的例子包括·氫氣酸、石肖酸、硫酸、氫氟酸、填 酸、硼酸和草酸。 牛 有機酸的例子包括··乙酸、丙酸、丁酸、戊酸、已酸、 庚酸、辛酸、壬酸、癸酸、草酸、順丁烯二酸、甲基^二 酸、己二酸、癸二酸、鎵酸、丁酸、苯六酸、花生四 酸、莽草酸、2 -乙基己酸、油酸、硬脂酸、亞油酸、亞油 烯酸、水楊酸、苯曱酸、對胺基苯甲酸、對甲苯碏酸、茉 磺酸、氯乙酸、二氯乙酸、三氯乙酸、三氟乙酸、、甲酸、 丙二酸、磺酸、苯二曱酸、反丁烯二酸、檸檬酸、酒^酽 、丁二酸、亞曱基丁二酸、甲基反丁稀二酸、檸康酸曱夂 基順丁烯二酸)、蘋果酸、戊二酸水解產物、順丁 酐水解產物、和苯二甲酸酐水解產物。 一-夂 用可以將這些化合物單獨使用,或者是其二或多個組合使 此類的pH調節劑是用來調整該組成物軸 較:是!至6。上…將該水解和縮合的-更低’ 調整到5至50 nm,然後以該pH調 ;
方法’產生了該所得組成物具有增強的以I 第24頁 \\312\2d-code\90-07\90108711.ptd 1286155 五、發明說明(21) 合適地選擇所使用pH調節劑的量,使得該組成物的pH是 在該範圍之内的值。 有機溶劑(B) 本發明之薄膜成形用組成物包含成分(A ),係通常溶 解或分散於有機溶劑(B )中。 該有機溶劑(B )可能至少包含一個選自醇溶劑,酮溶 劑,醯胺溶劑,酯溶劑和非質子溶劑所組成的族群之溶 劑。 醇溶劑的例子包括:一元醇,像是甲醇、乙醇、正丙醇 、異丙醇、正丁醇、異丁醇、二級丁醇、三級丁醇、正戊 醇、異戊醇、2-甲基丁醇、二級戊醇、三級戊醇、3-曱氧 基丁醇、正己醇、2-曱基戊醇、二級己醇、2-乙基丁醇、 二級庚醇、庚醇-3、正辛醇、2-乙基己醇、二級辛醇、正 壬醇、2, 6 -二甲基庚醇-4、正癸醇、二級十一醇、三甲基 壬醇、二級十四醇、二級十七醇、苯酚、環己醇、甲基環 己醇、3, 3, 5 -三曱基環己醇、苯甲醇和雙丙酮醇; 多元醇,像是乙二醇、1,2-丙二醇、1,3 - 丁二醇、戊二 醇-2, 4、2-曱基戊二醇-2, 4、己二醇-2,5、庚二醇-2, 4、 2-乙基己二醇-1,3、二甘醇、雙丙二醇、三甘醇和三丙二 醇; 以及多元醇的偏醚,像是乙二醇曱醚、乙二醇乙醚、乙 二醇丙醚、乙二醇丁醚、乙二醇己醚、乙二醇苯醚、乙二 醇-2-乙基丁醚、二甘醇甲醚、二甘醇乙醚、二甘醇丙醚 、二甘醇丁醚、二甘醇己醚、丙二醇曱醚、丙二醇乙醚、
C:\2D-CODE\90-07\90108711.ptd 第 25 頁 1286155 五、發明說明(22) 丙二醇丙醚、丙二醇丁醚、雙丙二醇曱醚、雙丙二醇乙醚 和雙丙二醇丙醚。 可以將這些醇溶劑單獨使用,或者是其二或多個組合使 用。 酮溶劑的例子包括:丙酮、甲基乙基酮、甲基正丙基酮 、甲基正丁基酮、二乙基酮、曱基異丁基酮、曱基正戊基 酮、乙基正丁基酮、甲基正己基酮、二異丁基酮、三甲基 壬酮、環己酮、2 -己酮、甲基環己酮、2,4 -戊二酮、丙酮 基丙酮、苯乙酮和小®香酮(fenchone )。其例子進一步 包括万-二酮,像是乙醯基丙酮、2, 4-己二酮、2, 4 -庚二 酮、3, 5 -庚二酮、2, 4 -辛二酮、3, 5 -辛二酮、2, 4 -壬二酮 、3, 5-壬二酮、5-曱基-2, 4-己二酮、2, 2, 6, 6-四曱基-3, 5 - 庚二酮、和1,1,1,5,5,5 -六氟-2,4 -庚二酮。 可以將這些化合物單獨使用,或者是其二或多個組合使 用 醯胺溶劑的例子包括:甲醯胺、N-甲基甲醯胺、N,N-二 甲基甲醯胺、N-乙基曱醯胺、N,N-二乙基曱醯胺、乙醯胺 、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-乙基乙醯胺、N, N -二乙基乙醯胺、N -甲基丙醯胺、N -曱基吡咯烷酮 (N-methylpyrrolidone ) 、N-甲醯基嗎琳 (N-formylmorpholine ) 、N-甲醯基旅σ定、N-甲醯基吼口各 啶、Ν -乙醯基嗎啉、Ν -乙醯基旅啶、和Ν -乙醯基吡咯啶。 可以將這些化合物單獨使用,或者是其二或多個組合使 用0
C:\2D-CODE\90-07\90108711.ptd 第26頁 1286155 五、發明說明(23) 酯溶劑的例子包括:碳酸二乙酯、碳酸次乙酯、碳酸丙 二酯、乙酸甲酉旨、乙酸乙酯、T -丁内酉旨、7 -戊内酯、乙 酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸異丁酯、乙酸 二級丁酯、乙酸正戊酯、乙酸異戊酯、乙酸3 -曱氧基丁酯 、乙酸曱基戊酯、乙酸2-乙基丁酯、乙酸2-乙基己酯、乙 酸苯曱酯、乙酸環己酯、乙酸曱基環己酯、乙酸正壬酯、 乙醯乙酸甲醋、乙醯乙酸乙酯、乙二醇單曱醚乙酸酯、乙 二醇單乙醚乙酸酯、二甘醇單曱醚乙酸酯、二甘醇單乙醚 乙酸酯、二甘醇單正丁醚乙酸酯、丙二醇單甲醚乙酸酯、 丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單丁 醚乙酸酯、雙丙二醇單曱醚乙酸酯、雙丙二醇單乙醚乙酸 酯、乙二醇二乙酸酯、甲氧基三甘醇乙酸酯、丙酸乙酯、 丙酸正丁酯、丙酸異戊酯、草酸二乙酯、草酸二正丁酯、 乳酸甲酯、乳酸乙酯、乳酸正丁酯、乳酸正戊酯、丙二酸 二乙酯、苯二甲酸二甲酯、和苯二甲酸二乙酯。 可以將這些化合物單獨使用,或者是其二或多個組合使 用。 非質子溶劑的例子包括:乙腈、二曱基亞砜、N,N,Ν’, Ν’ -四乙基硫醯胺、六甲基磷醯三胺、Ν-甲基嗎啉酮 (mor pho lone) 、Ν—甲基口 比口各(pyrrole) 、N-乙基 ϋ比 口各、 Ν-甲基-Δ3-吼σ各琳(pyrroline) 、Ν-甲基旅咬、Ν-乙基 旅咬、Ν,Ν-二曱基旅併、Ν-曱基口米唾(imidazole)、Ν-曱 基-4 -旅σ定酉同(piperidone ) 、Ν-甲基-2 -旅咬酉同、Ν-甲基 -2 -吼口各烧删(pyrrolidone) 、1,3 -二甲基-2 - 口米峻琳酮
C:\2D-CODE\90-07\90108711.ptd 第27頁 1286155 五、發明說明(24) (imidazolidinone )、和1 g (pyrimidinone ) 〇 上面所列舉之有機溶劑較佳為 之有機溶劑: j化予式(4 )所示 R80(CHCH3CH20)eR9 其"8和R9分別獨幻也表*氫原子,二4 ) 碳原子之炫基和CH3C〇_所組成的族 價機ϋ個 為1或2的整數。 早彳貝有祛基,且e 可以將這些有機溶劑單獨使用,或 混合物使用。 疋作馬具一或多個 ^本發明:水解和縮合該化合物(1)至( 如上面所列舉的相同溶劑。 了以使用 本發明組成物之製造方法的例子如下。 水斷續或連續地加入合右兮彳人 、’ /合划稀釋 八3有该化合物(1)至(3)溶解於1 士 4 =°在該操作中,可以預先將特殊驗性 加二 散於水中。該例子中反應溫度通常為0至 ^解或分 15至9 0 °C。 i 心佳為 其他添加物 有機聚合 和三氮烯 可以將像是膠態氧化矽(矽膠)、膠態氧化鋁 物、、界面活性劑、矽烷偶合劑、自由基產生劑 的成巧ΐ ^本發明所得到之薄膜成形用組成物 /膠氧化石夕為懸浮液,其包含,例如··任何上 水性有機溶劑,以及分散於其中之高純度石夕酸㈤(= 第28頁 C:\2D-CODE\90-07\90108711.ptd 1286155 五、發明說明(25) 矽)。其平均粒子直徑通常為5至30 nm,較佳為1〇至20 nm ;並且其固體濃度通常約為以重量計10至40%。該膠態氧 化石夕的例子包括:由 Nissan Chemical Industries,Ltd. 所製造之甲醇矽溶膠和異丙酵矽溶膠,以及由Catalysts & Chemicals Industries Co·,Ltd·所製造之〇scal。 該膠態氧化鋁的例子包括:由Nissan Chemical
Industries,Ltd·所製造之 Alumina Sol 520、100 和 200 ’以及由 Kawaken Fine Chemicals Co.,Ltd·所製造之 Alumina Clear Sol 和Alumina Sol 10 和132 。
該有機聚合物的例子包括:具有糖鏈結構之化合物、乙 烯醯胺聚合物、(曱基)丙烯酸聚合物、芳香族乙稀化合 物、dendrimers、聚醯亞胺類、聚(醯胺酸)類、聚亞芳 基類、聚醯胺類、聚琳(p〇lyqUin〇xaline)、聚峰二 唑(polyoxadiazoie)、氟聚合物、以及具有聚(氧化j — 基)結構之化合物。 70 该具有聚(氧化伸烷基)結構之化合物的例子包括··具 聚(氧化亞甲基)結構、聚(氧化伸乙基)結構、聚(氧化伸 丙基)結構、聚(四氫呋喃)結構、聚(氧化伸丁基)結 其他之化合物。 —^
〃特殊例子包括:像是聚氧亞甲基烷基醚類、聚氧 基烧基㈣貞、聚氧伸乙純基苯細類、聚氧伸 醚類、聚氧伸乙基羊毛脂衍生物 的氧化伸乙基衍生物1氧伸乙基/聚氧伸丙甲基之夜: 聚物、和聚氧伸乙基/聚氧伸丙基烷基喊類之醚型化4
1286155 五、發明說明(26) ;像是聚氧伸乙基甘油脂肪酸酯類、聚氧伸乙基山梨糖醇 酐脂肪酸㈣、聚氧伸乙基山梨糖醇脂肪酸醋类員、和聚氧 伸乙基脂肪酸烷醇酿胺硫酸鹽類之醚_酯型化合物;以及 像是聚乙二醇脂肪酸醋類、乙二醇脂肪酸醋類、脂肪酸甘 油8旨類 '脂肪酸聚甘油8旨類、山梨糖醇軒脂肪酸醋類、丙 -酵脂肪酸s旨类員、和蔗糖脂肪酸酯類之醚一酯型化合物。 伸乙基/聚氧伸丙基之嵌段共聚物的例子包括具 有下列嵌段結構之一的化合物: -⑴ r(Y)k--CX)j-(Y)k-(X)1- ί ? ί表示,CH(CH^ j為1㈣的整 數,k為ίο至99的整數;且至9〇的整數。 上面所列舉之化合物較佳為· 、聚氧伸乙基/聚氧伸丙基之嵌段二 Λ基烷基醚類 聚氧伸丙基烷基醚類之喊型化、和聚巩伸乙基/ 酸酿類、聚氧伸乙基山梨;伸乙基,油脂肪 山梨糖醇脂肪酸酯類。 …曰曰類和聚氧伸乙基 用可以將這些化合物單獨使用,或者是其二或多個組合使 :界面活性劑的例子包括:非離子性界面 2二:卜=界面活性劑和兩性界面活性劑1 。較佳的是,化學界面活性;(和
1286155 五、發明說明(27) 该氟化學界面活性劑為含有在至少一個選自末端、主鏈 和支鏈的位置上’具有氟烷基或氟伸烷基之化合物的界面 活性劑。其例子包括: 1,1,2,2-四氟辛基1,1,2,2-四氟丙基鱗、 1,1,2,2-四氟辛基己基_、 八乙二醇二(1,1,2, 2 -四氟丁基)醚、 乙一醇1,1,2,2,3,3-六1戊基醚、 八丙二醇二(1,1,2, 2 -四氟丁基)醚、 丙一醇二(1,1,2,2,3,3 -六敦戊基)鱗 全氟十二烷基磺酸鈉、 -二曱基-N-羧 1’ 1’ 2, 2, 8,8,9,9,10,10 -十氟1十二烧、 1,1,2, 2, 3, 3-六氟癸燒、 N - [3-(全氟辛烷亞磺醯胺基)丙基]—n,n 亞曱基銨甜菜驗、 全氟烷基亞磺醯胺基丙基三曱基銨鹽、 全就烧基-N-乙基石黃酿基甘胺酸鹽、 雙(N-全氟辛基磺醯基乙基胺基乙基)磷酸鹽、和 單全氟烷基乙基磷酸鹽。 商業上可取得之此類氟化學界面活性劑的產品包括:在 商品名稱Megafac F142D 、F172 、F173 和F183 (由 Dainippon Ink & Chemicals,Inc·所製造的);F-Top、 EF301 、EF303和EF352 (由New Akita Chemical Company 所製造的);Fluorad FC - 430 和 FC - 431 (由 Sumitomo 3M Ltd·所製造的);Asahi Guard AG 710 和Surf Ion S-382、
\\312\2d-code\90-07\90108711.ptd 第 31 頁 1286155 五、發明說明(28) SC-101、SC-102、SC-103、SC-104、SC-105 和SC-106 (由 Asahi Glass Co·,Ltd·所製造的);BM- 1 0 00 和 BM-1100 (由 Yusho Κ· Κ·所製造的);以及NBX-15 (由 NEOS Co., Ltd·所製造的)之可取得的產品。其中較佳為Megafac F172 、BM-1000 、BM-1100和NBX-15 〇
該矽酮界面活性劑的例子包括SH7PA、SH21PA、SH30PA 和ST94PA (均由Dow Corning Toray Silicone Co·, Ltd. 所製造的)。其中較佳為SH28PA和SH30PA。 以重量計每1 00份之成分(A )中,所使用此類界面活性 劑的量通常是以重量計0·0 0 0 1至10份(就完全水解和縮合 的產品而吕)。 可以將這些界面活性劑單獨使用,或者是其二或多個組 合使用。 該石夕烧偶合劑的例子包括: 3-縮水甘油基氧丙基三甲氧基矽烷、 3-胺基縮水甘油基氧丙基三乙氧基矽烷、 3 -甲基丙烯基氧丙基三甲氧基矽烷、 3-縮水甘油基氧丙基甲基二甲氧基矽烷、 1- 甲基丙烯基氧丙基甲基二甲氧基矽烷、 3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、 2- 胺基丙基三甲氧基矽烷、2—胺基丙基三乙氧基矽烷、 Ν-(2-胺基乙基)—3 一胺基丙基三甲氧基矽烷、 Ν -(2-胺基乙基)—3一胺基丙基甲基二甲氧基矽烷、 3- 脲基丙基三甲氧基矽烷、3-脲基丙基三乙氧基矽烷、
C:\2D-CODE\90-07\90108711.ptd 第32頁 1286155 五、發明說明(29) N-乙氧基羰基-3_胺基丙基三甲氧基石夕烷、 N-乙氧基羰基_ 3 _胺基丙基三乙氧基石夕烷、 N-二乙氧基碎炫基丙基三伸乙基三胺、 N-三曱氧基矽烧基丙基三伸乙基三胺、 10 -三曱氧基矽烧基-1,4, 7-三吖癸烧、 10-三乙氧基矽烷基-1,4, 7 -三吖癸烧、 9-三甲氧基矽烷基-3, 二吖壬基乙酸酯、 9_三乙氧基矽烷基-3, 6-二吖壬基乙酸酯、 N-苯甲基-3 -胺基丙基三甲氧基矽烷、 N-苯曱基-3-胺基丙基三乙氧基矽烷、
N-苯基-3 -胺基丙基三甲氧基矽烷、 N-苯基-3 -胺基丙基三乙氧基矽烷、 N-雙(氧伸乙基)一3一胺基丙基三甲氧基矽烷、和 N-雙(氧伸乙基)-3—胺基丙基三乙氧基矽烷。 多個 可以將這些矽烷偶合劑單獨使用,或者是其二。」 合使用。 八一 ^ 該自由基產生劑的例子包括:過氧化異丁醯 雙(新癸醯基過氧)二異丙基 異丙苯基過氧新癸酸酯、二_正 二異丙基過氧二碳酸酯、 軋一妷心
1,1,3,3-四甲基丁基過氧靳癸酸酯、 雙^4-三級丁基環己基)過氧二碳酸酯、 卜環己基-1-甲基乙基過氧新癸酸酯、 二-2-乙氧基乙基過氧二碳酸酯、
C:\2D-CODE\90-07\90108711.ptd 第33頁 ί286]55 五、發明說明(30) 2乙基己基過氧一碳酸_、一 ,基丁基過氧二嫂酸醋、二級己基過乳新癸酸醋 :(Μ基-3— f氧基丁基)過氧二端酸酯、 :級Τί過氧新癸酸醋、過氣化2, 4-二氯苯甲醯、 、、及已基過氧新戊酸酯、三級 過氧化3,5,5 -三甲基己醯、過梟二=羊/ •夂酉曰、 過氧化硬脂醯、m3—四甲;化:醯、過氧化月桂醯 略、過氧化㈣酿、 甲基丁基過氧-2-乙基己酸 h5if =二,_2,5_二(2-乙基己酿基過氧)己烧、 %己基-1-甲基乙基過氧〜2— 乳J已烷 ,級己基過氧-2-乙基己酸酯、土已酸酯、 二級丁基過氧-2-乙基己酸酯、 過氧化-間-甲苯甲醯基苯甲醯、 二級丁基過氧異丁酸酯、二-三°氣化苯甲醯、 烷、 —、、丁基過氧-2~甲基環己 1 1-雙(三級己基過氧)_3, 3, 5〜一 雙(三級己基過氧)環己烷、〜曱基環己烷、 i,1-雙(三級丁基過氧)_3,3,5、_ 1,卜雙(三級丁基過氧)環己烷、〜曱基環己烷、 2’ 2雙(4, 4 -二-三級丁基過氧環已 1二卜雙(三級丁基過氧)環癸烷、土)丙烷、 二級己基過氧異丙基單碳酸酯、 三級丁基過氧順丁烯二酸酯、 二級丁基過氧-3, 3, 5-三曱基己酸醋、 C:\2D-C0DE\90-07\90108711.ptd 第34頁
!286155 五、發明說明(31) 三級丁基過氧月桂酸酯、 2三5級Ϋ:ίΐ’5_二甲苯甲醯基過氧)已烷、 一、、 土3^氧異丙基單碳酸g旨、 丁基過氧—2一乙基己基單碳酸酯、 二級己基過氧苯甲酸酯、 二:基―2’5—二(苯甲醯基過氧)己烷、 烷 二:丁Ϊ過氧乙酸醋、2,2-雙(三級丁基過氧)丁 二級丁基過氧苯甲酸酯、 巩)丁 =丁一基4’4-雙(三級丁基過氧)戊酸酯、 一二級丁基過氧異苯二甲酸酯、 01雙(二級丁基過氧)二显丙其装、 過氧化二異丙苯、 -丙基本 2晶二F基_2,5-二(三級丁基過氧)己烷、 k虱化二級丁基異丙苯、過 _ 對一 1烧過氧化氫(Pienthanebh一;;二、,及丁貌、 -思工成丁基過虱)己炔~3、 一異丙基本過氧化氫、過氧化三級 以重量計每100份之聚合物中, 的量較佳是以重量計0.1至10份。 頰自由基產生 J以將廷些自由基產生劑單獨 組合使用。 4者是复-上 或多個 L〗,3, 3-四甲基丁基過氧化氫、昱甲基矽烷、 三广己基過氧化氫、三級丁基過氧過乳化氫、 2,3_二f基-2,3-二苯基丁烷 飞# 劑的 第35頁 C:\2D-C0DE\90-07\90108711.ptd 1286155 五、發明說明(32) 該三氮烯化合物的例子包括 1,2-雙(3, 1,3-雙(3, 1,4-雙(3, 雙(3, 3-二 雙(3, 3-二 雙(3, 3-二 雙(3, 3-二 2, 2-雙[4-基]-1,1,1, 2, 2-雙 Μ-ΐ , 3 , 5 - 三 ( 3-二甲基三氮烯基)苯、 3-二甲基三氮稀基)苯、 3-二甲基三氮烯基)苯、 曱基三氮烯基苯基)醚、 曱基三氮烯基苯基)甲烷、 甲基三氮烯基苯基)硬、 曱基三氮烯基苯基)硫醚、 (3,3-二甲基三氮烯基苯氧基)苯 3,3,3-六氟丙烧、 (3, 3 -二甲基三氮烯基苯氧基)苯基]丙烷 3, 3-二曱基三氮烯基)苯、 2.7- 雙(3,3-二甲基三氮烯基)-9,9-雙[4- (3,3-二甲基 三氮烯基)苯基]苐、 2,7-雙(3, 3-二甲基三氮烯基)-9, 9-雙[3-曱基-4-(3, 3-二甲基三氮烯基)苯基]苐、 2, 7-雙(3, 3-二曱基三氮烯基)-9, 9-雙[3-苯基-4 -(3, 3-二甲基三氮烯基)苯基]苐、 # 2.7- 雙(3, 3-二甲基三氮烯基)-9, 9-雙[3-丙烯基-4 -(3, 3-二甲基三氮烯基)苯基]苐、 2.7- 雙(3,3-二甲基三氮烯基)-9,9-雙[3-氟-4- (3,3-二曱基三氮烯基)苯基]第、 2,7-雙(3, 3-二甲基三氮烯基)-9, 9-雙[3, 5 -二氟-4-(3,3 -二曱基三氮烯基)苯基]苐、和
C:\2D-CQDE\90-07\90108711_ptd 第36頁 1286155 五、發明說明(33) 2, 7-雙(3, 3-(3, 3-二甲基 可以將這些 組合使用。 膜成形用組 甲基三氮烯基) 氮浠基)苯基]第雙[3~三氟甲基— 4-氮烯化合物單獨使用’或者是其二或多個 本發明之薄膜成形用M成物 。例如,可以藉由將化合物⑴/;備:f並不特別地限制 或斷續地將水加人其中來 =二於溶劑中,連續 ,然後將成分(B)加入其中,來^解/;細5而得到成分(A) 本發明組成物之製備方法殊广子组成物。 11)。 0特殊例子包括下列方法1 )至 1) 一種方法,其中係將定 (A)之化合物(i )至n、 、7 ,加入含有構成成分 劑之混合物中,來摔作水解、殊鹼性化合物、和有機溶 2) -種方法,合反應。 (Α) 物、和有機溶劑之混合物 特殊驗性化合 3) -種方法,其中係蔣定旦αα铩作水解和鈿合反應。 入含有構成成分(Α)之化合物水和特殊鹼性化合物,加 物中,來操作水解和縮合口反應。至(3)和有機溶劑之混合 4) 一種方法,其中孫腺々旦 續或斷續地加入含有構成成二“、水和特殊鹼性化合物’連 機溶劑之混合物中之化合物⑴至(3)和有 U n、土 Γ來作水解和 '縮合反應。 ‘ ,/、中係將定量的構成成分(A)之化合物(1) 第37頁 C:\2D-CODE\90-07\90108711.ptd 1286155 五、發明說明(34) 至(3),加入含有右德w十 合物中,步钎从’有械 >谷劑、水和特殊鹼性化合物之混 6)-種ί: ΐ解和縮合反應。 至(3),連續’或斷、:係將定量的Μ成成分(Α)之化合物⑴ 化合物之混合4勿中'來含有有機㈣卜水和特殊驗性 7)-種方法,其尹伟二:#縮合反應。 至(3 ),加入含右古,疋置的構成成分(幻之化合物(]) 合物中,來操作水解和=容入劑、水和特殊驗性化合物之混 得溶液中。 、’'5 口反應,然後將pH調節劑加入所 (1)至(3),冓成成分(A)之化合物 :混合物中’來操作水解和縮二驗性化合物 至一定濃度之後,將PH調節劑加2二然後在該溶液濃縮 9) 一種方法,其中係以J 2所付溶液中。 方法1)至8)中所得的溶液。 有機溶劑來萃取上述任何 1 〇) —種方法,其中係以另一 '方法1)至8)中所得溶液之有—機ϋ溶劑來取代上述任 1 一種方法,其中以另一個有w 方法1)至8)中所得的溶液,係以」谷蜊來萃取上述任何 因此所得到本發明之組成物的總:::機溶劑來取代。 叶2至30 % 。根據其用途來適當地=遒度較佳為以重量 組成物的總固體濃度為以重量計2 / 1其固體濃度。當該 僅得到具有適當厚度之塗層薄膜,%時,該組成物不 穩定度。 且也具有較佳的儲存 C: \2D-C0DE\90'07\90108711·ptd 第38頁 1286155 五、發明說明(35) ▲以濃縮或是用有機溶劑(β )稀釋的方法,根據需要來 調整該組成物的總固體濃度。 +可以利用像是旋轉塗佈法、浸潰塗佈法、轆式塗佈法或 噴鍍法之塗佈技術,將本發明之組成物應用於像是矽晶圓 、S i 02晶圓或S i N晶圓之基板上。 可以操作該塗佈操作,來形成具有乾量基準(dry basis )厚度:在單面塗佈的例子中約為〇· 〇5至2. 5 ,或是在 雙面塗佈的例子中約為〇. i至5. 〇,之塗層薄膜。其後, 可以在常溫下乾燥,或是在約8〇至6〇〇 r的溫力:埶乾 塗:薄膜’通常約5至24〇分鐘。因此,可以形成、透 明或大分子的絕緣膜。 在该操作中’可以例如,在空 、 & 中,名畫处丁 . H ^ ^ Τ 在氣乳或虱氣氛圍 中在真二下、或疋在具有控制的氧濃度之減壓 二、供箱、火爐或其他來操作加熱。也可以使用 或紫外線之輻射,來形成塗層薄膜。 電子束 為了控制該塗層薄膜的固化速率,可以 階式加熱’或是適當地選擇像是: 要來使用 之環境。 疋虱孔二乳、氧氣或減壓 因此所得到本發明之矽石基骐 以⑽,較佳為UM」g/cin3,更佳吊,〇·35Μ·2 如果該薄膜的密度低於〇.35 g/cm3,則該1且〇 g/cm3。 機械強度。另-方面’如果其密产超過具有損害的 法得到低的介電常數。 又0 ^ · 2 g/C1"3,則無 當以B J Η方法來檢驗本發明 的矽石基膜 之孔徑分佈時
(36) " !286155 j其中無觀察到1 〇 nm或更大之孔隙。該薄膜因此適合用 來作為細線之間絕緣用之隔層絕緣膜材料。 再者’本發明之矽石基膜的特色為具有低的吸水性。例 ^ ’當將該塗層薄膜置於127 。(:、2. 5 atm及100 % RH之環 土兄中一小時,然後以丨R光譜儀在該塗層薄膜上觀察不到吸 水量。 可以藉由在製備該薄膜成形用組成物時,控制用於本發 明中作為化合物(1 )之四烷氧基矽烷的量,來調整吸水 性。 本發明之矽石基膜的介電常數通常為2· 6至丨· 2,較佳為 2.5至1.2,更佳為2.4至1.2。 因此所得到之隔層絕緣膜,在PCT之後的介電常數特性 ’在PCT之後的CMP阻抗力,以及在PCT之後對基板的黏著 性是優良的。因此,該塗層薄膜有用於··像是18丨s、系統 LSIs、DRAMs、SDRAMs、RDRAMs 和D-RDRAMs 的半導體元件 用之隔層絕緣膜或蝕刻終止膜,像是半導體元件用之表面 塗層薄膜的保護膜,應用多層絕緣塗料之半導體製造方法 用之隔層,多層印刷電路板用之隔層絕緣膜,以及液晶顯 示裝置用之保護或絕緣膜之應用。 本發明將參照下列實施例作更詳細說明如下。然而,下 列”兒明只顯示本發明的一般具體貫施例,並應了解本發明 並不被解釋為受到該說明限制。 在下列的貫施例和比較例中’除非另外標明,所有”份,, 和π百分率π都是以重量計。
1286155
以下列方法來評估各種性質。 迴轉丰牿 、 在下列的條件下,以凝膠滲透層析法(Gpc 量折 射率、黏度或光散射)來測量。 樣品溶液:將矽烷化合物的水解和縮合之產物,以含有 10 mM LiBr之甲醇稀釋至〇. 25 %的固體濃度,而製備Gpc (測量折射率、黏度或光散射)用之樣品溶液。 GPC系統:型號GPC_8020,由T〇s〇h c〇rp.所黎』造 管柱:Alpha 5000/3000,由 T〇s〇h c〇rp.所^ 造 黏度偵測器和光散射偵測器:型號τ_6〇雙讀^,由 Visco Tech Co·所製造 乂 運載〉谷液·含有10 mM LiBr之甲醇 載體供給速率·1 ml/inin 管柱溫度:4 0 °C 皇PCT之德的介電當齡 以旋轉塗佈法將該組成物樣品應用至8吋矽晶圓上。將 該經塗佈基板先在90 °C熱板上乾燥3分鐘,接著在2〇〇乞 氮氣氛圍中乾燥3分鐘;然後在真空中(5〇 mT〇rr ) 、45〇 。(:熱板上燒熱30分鐘。在1〇〇它、ι〇〇 % RH和2大氣壓的 條件下’將所得薄膜加以1小時PCT。以氣相沉積法,在該 薄膜上形成銘電極圖案。因此,製造出測量介電常數用之 樣品。以由Yokogawa-Hewlett-Packard,Ltd.所製造之電 極HP1 6451 B和精密LCR儀器HP4284A,在100 kHz的頻率下 檢驗該樣品,以CV法來測定該塗層薄膜的介電常數。
1286155 發明說明(38) 在PCT之德CMP的阻杭六 以旋轉塗佈法將該組成物樣品應用至8吋矽晶圓上。將 ,,,佈基板先在90 °c熱板上乾燥3分鐘,接著在20〇 。〇 氮氣氛圍中乾燥3分鐘;然後在真空中(5〇 mT〇rr ) 、45〇 C熱板上燒熱30分鐘。在1〇〇它、1〇〇 % RH和2大氣壓的 條件下’將所得薄膜加以1小時pCT。 在下列的條件下’將所得的塗層薄膜拋光。 泥漿··矽石/過氧化氫系統 拋光壓力:1 60 g/cm2 拋光時間:1 8 0秒 在C Μ P之後,以表面檢驗具有Μ 〇,〇 〇 〇 1 χ照度的燈來檢⑩ 驗该塗層薄膜的外表,基於下列的標準來評估CMp阻抗 力0 〇·在邊塗層薄膜的表面上無法目視觀察到裂縫。 X :在該塗層薄膜的表面上目視觀察到裂縫。 塗層薄膜的黏荖柹 以旋轉塗佈法將該組成物樣品應用至8吋矽晶圓上。將 該經塗佈基板先在90 t熱板上乾燥3分鐘,接著在2〇〇 t 氮氣氛圍中乾燥3分鐘;然後在真空中(5〇 mT〇rr ) 、450 °C熱板上燒熱30分鐘。在loo它、ι〇〇 % rh和2大氣壓的 條件下,將所得薄膜加以i小時PCT。以環氧樹脂將十個柱 螺栓銷固定於所得到經塗佈基板上。應用環氧樹脂之後, 在150 °C固化1小時,以無水芒硝(Sebastian)法將該桎螺 栓銷拔出,基於下列的標準來評估該塗層薄膜的黏著性。
1286155 五、發明說明(39) 膜之間個柱螺栓銷’在該矽晶圓和該塗層薄 晶圓和該塗層薄膜之間產生剝落。 將5 7 0 g蒸餾乙醇、丨 六 甲基氫氧化銨水溶液,導入§以:;2和3° g之四 將内容物攪拌並同質化。在、^ 1的可拆式燒瓶中。 备《· J貝化 在5亥〉谷液中加人:一田 持二二烧和209 g四乙氧基石夕烧的混合物。將所得‘二唯 持在55 r反應2小時。冰兮冰发由^物將所付/奋液維 。接著,以50。/在心液中加入300 g丙二醇丙醚 1"'二2 將所得溶液遭縮至其濃度達到 10 g之;〇 Π =縮合的產物含量而言卜其後,將 到反應混合物(ΓΓ^於丙一酵丙驗、加入該濃縮液而得 迴二b:得到之縮合和其他反應之產物,具机“m之 實施例2 除了使用1 0 % 口底口林士、—、—七^ , 得到反應混㈣(2)σ成““列1中的相同步驟。因此, 因此所得到之縮合和1 迴轉半徑。 、他反應之產物,具有13.0 nm之 實施例3 °/〇 氧紅水〉谷液之外,操作如合成實施例1中的相同步 第43頁 C:\2D-CODE\90-07\90108711.ptd 1286155 五、發明說明(40) 驟。因此,得到反應混合物(3 )。 因此所得到之縮合和其他反應之產物,具有1 5. 〇 nm之 迴轉半徑。 ilAA施例4 除了使用1 0 %氫氧化鈉水溶液來取代1 〇 %四甲基氫氧 化銨水溶液之外,操作如合成實施例1中的相同步驟。因 此,得到反應混合物(4 )。 因此所得到之縮合和其他反應之產物,具有丨4. 8 nm之 迴轉半徑。 1成實施例5 將470.9 g蒸餾乙醇、226.5 g離子交換水和17.2 g之25 %四甲基氫氧化銨水溶液,導入以石英所製的可拆式燒瓶 中。將内容物攪拌並同質化。在該溶液中加入44· 9 g甲基 二甲氧基矽烷和6 8 · 6 g四乙氧基矽烧的混合物。將所得溶 液維持在5 5 °C反應2小時。在該溶液中加入5 0 g之2 0 % 硝酸水溶液。將所得混合物充分攪拌並冷卻至室溫。在該 溶液中加入4 0 0 g丙二醇丙醚。接著,以5 0 °C蒸發器,將 所得溶液濃縮至其濃度達到1 〇 % (就完全水解和縮合的產 物含量而言)。其後,將10 g之10 %順丁烯二酸溶液於丙 二醇丙醚、加入該濃縮液而得到反應混合物(5 )。 因此所得到之縮合和其他反應之產物,具有2 〇 · 9 nm之 迴轉半徑。 合成實施例6 除了使用2 5 %四丁基氫氧化銨水溶液來取代2 5 %四曱
C:\2D-CODE\90-07\90108711.ptd 第44頁 1286155 、發明說明(41) 土氣氧化銨水溶液之外,操作如合成實施例5中的相同步 驟。因此’得到反應混合物(6 )。 因此所得到之縮合和其他反應之產物,具有2 2 8 nm之 迴轉半徑。 · 、=了使用丙二醇乙醚來取代丙二醇丙醚之外,操作如合 成實施例5中的相同步驟。因此,得到反應混合物(7 )。 因此所得到之縮合和其他反應之產物,具有2 〇 · 8 ηηι之 迴轉半徑。 ·
〇將470. 9 g蒸餾乙醇、226· 5 g離子交換水和17· 2 §之25 /〇四甲基氫氧化銨水溶液,導入以石英所製的可拆式燒瓶 中將内谷物攪拌並同質化。在超過2小時,在該溶液中 加入4 4 · 9 g曱基三甲氧基矽烷和6 8 · 6 g四乙氧基矽烷的混 合物。將所得溶液維持在59 I反應5小時。在該溶液中Z 入5 0 g之2 0 %硝酸水溶液。將所得混合物充分攪拌並冷 卻至至溫。在該溶液中加入4 〇 〇 g丙二醇丙_。接著,以 5 0 °C蒸發器,將所得溶液濃縮至其濃度達到丨〇 % (就完 全水解和縮合的產物含量而言)。其後,將1 0 g之1 〇 %
順丁烯二酸溶液於丙二醇丙醚、加入該濃縮液而得到反廉 混合物(8 ) 。 ^ 因此所得到之縮合和其他反應之產物,具有1 7· 9 nm之 迴轉半徑。 合成實施例9
C:\2D-CODE\90-07\90108711.ptd
1286155 五、發明說明(42) 將470· 9 g蒸餾乙醇、233· 3 g離子交榼 %氫氧化鉀水溶液,導入以石英所製的环和1 〇·、4 g之25 内容物攪拌並同質化。在該溶液中加入4 :式燒,中。將 2烧和四乙氧基石夕烧的混合物。將所得溶; f 2 C反應2小時。在該溶液中加入5〇 §之2〇 夺 >谷液。將所得混合物充分攪拌並冷卻至宏、w ^ ,χ 丨王至溫。在該溶液中 力二侧g丙二醇丙醚。接著,以5() t蒸發器,將所得溶 =浪縮至其濃度達到10 % (就完全水解和縮合的產物含 罝而言)。其後,將10 g之10 %順丁烯二酸溶液於丙二 醇丙醚、加入該濃縮液而得到反應混合物(9 )。 因此所得到之縮合和其他反應之產物,具有24.6 nm 迴轉半徑。 〃 · 金-成實施你μ η 將470.9 g蒸餾乙醇、233·3 g離子交換水和1〇·4 g<25 %氫氧化鉀水溶液,導入以石英所製的可拆式燒瓶中。將 内谷物攪拌並同質化。在超過3 〇分鐘,在該溶液中加入: 44· 9 g甲基三曱氧基矽烷和68· 6 g四乙氧基矽烷的混合物 。將所得溶液維持在52 °C反應1小時。在該溶液中加入5〇 g之2 0 %硝酸水溶液。將所得混合物充分攪拌並冷卻至室
溫。在該溶液中加入4 〇 〇 g丙二醇丙醚。接著,以5 〇 蒸 發器’將所得溶液濃縮至其濃度達到1 〇 % (就完全水解矛: 縮合的產物含量而言)。其後,將1 0 g之1 〇 %順丁烯二酸 溶液於丙二醇丙醚、加入該濃縮液而得到反應混合物(i G
第46頁 1286155
具有21. 6 nm之 因此所彳寸到之縮合和其他反應之產物, 迴轉半徑。 合成比較例1 %四甲基氫氧化銨 相同步驟。因此, 除了使用1 0 % ϋ比咬水溶液來取代1 〇 水溶液之外,操作如合成實施例1中的 得到反應混合物(1 1 )。 具有3 · 8 nm之迴 因此所得到之縮合和其他反應之產物 轉半徑。 合成比較例2
將154· 甲基三曱氧基矽烷、288.83 g四曱氧基矽烷 和250 g之蒸餾丙二醇乙醚,導入以石英所製的可拆式燒 瓶中。在超過1小時,在該溶液中逐滴地加入2 9 7 g含有丄〇 g順丁烯二酸溶解於其中之離子交換水。將所得溶液在5〇 C反應3小時而得到反應混合物(丨2 )。 因此所得到之縮合和其他反應之產物,具有〇 · 2 之迴 轉半徑。 實施例1 將合成實施例1中所得到之反應混合物〇 )經過具有 0.2 # m開口直徑之鐵氟龍過濾器過濾,而得到本發明之 薄膜成形用組成物。 以旋轉塗佈法將所得組成物應用至矽晶圓上。 在PCT之後’該塗層薄膜具有低至2· 27的介電常數,並 且即使加以CMP也無受到損毁。再者,在pCT之後,該塗層 薄膜對該矽晶圓的黏著性令人滿意。
1286155 五、發明說明(44) 實施例2至1 0
從表1所示之個別的 且以實施例1中相同的 於表1。 才才料來製造薄膜成形用組成物,並 #法來評估。所得到評估結果顯示
PCT之後 黏著性 ο Ο Ο _〇 Ο Ο Ο ο ο ο
i應混 pct 之 ί 介雷堂
PCT之後 CMP阻抗力 〇 〇 — 〇 ’ 〇 — 〇—~~ δ δ ο ο ^ ~ο~ 比較例1 除了使用合成比較例1中所得的反應混合物 ,如實施例i中相同的方法來形成並評估塗;壤=)之外 儘管在進行PCT後之塗層薄膜的介電常數^ / 、。 相當低;但是該塗層薄膜在CMP後受到表面2^67,其為 在pct之後,該塗層薄膜的黏著性之評估結^毁。再者, 柱螺栓銷,在該矽晶圓和該塗層薄膜之門",關於五個 落。 、B界面上產生剝
1286155
五、發明說明(45) 比較㈣ 除了使用合成比較例2中所得的反應混合物(i ” ,如貫施例1中相同的方法來形成並評估塗層薄膜。 在進行PCT後之塗層薄臈的介電常數高至3· 88。再者, 在PCT之後,該塗層薄膜的黏著性之評估結果,關於三個 柱螺栓銷’在該石夕晶圓和該塗層薄膜之間界面上產生剝 落。 根據本發明,可以經由在特殊鹼性化合物的存在下,將 至少一個烷氧基矽烷水解和/或縮合,來提供一種薄膜成 形用組成物(隔層絕緣膜材料),其在PCT之後的介電常 數特性,在PCT之後的CMP阻抗力,以及在PCT之後對基板 的黏著性優良。
C:\2D-CODE\90-07\90108711.ptd 第49頁 1286155 圖式簡單說明 « C:\2D-CODE\90-07\90108711.ptd 第50頁
Claims (1)
1286155 六、申請專利範圍
1 · 一種薄膜成形用組成物,其包含: (A)在水以及至少一個選自四烷基氫氧化銨、 機胺和金屬氫氧化物所組成的族群之化矢 …個選自下列化學式⑴所示化合物、下:存化^ 所示化口物和下列化學式(3)所示化合物所組成的族 矽烷化合物水解並縮合,所得到的水解和縮合產物、; RaSKOR1 )4.a 其中R表示氫原子、氟原子或單價有機基 機基;且a為1或2之整數; ;R1表示單價有 Si(0R2)4 其中R2表示單價有機基; R3“R4〇VbSi - (R7)d — Si(0R5)3_cR6c (3 ) 其中R3至R6可能是相同或不$,並且分別表示單價有機基 二t和c可能是相同或不同,並且分別為〇至2的數目;表 不氧原子、伸苯基、或是由—(CH2)n_所示官能基,其中n為 1至6的整數;且d為〇或1 ;以及 (B )有機溶劑。 (2
如,凊專利範圍第1項之薄膜成形用組成物,其中該 四烷f虱氧化銨包括四甲基氫氧化銨;月旨環族有機胺包栝 哌啶何生=、哌畊衍生物、吡咯啶衍生物、二吖雙環辛炼 二了吖雙裱壬烷和二吖雙環十一烯;且金屬氫氧化物包枯 氫氧化鈉、氫氧化鉀和氫氧化鋰。 —3/如申清專利範圍第1項之薄膜成形用組成物,其中, 母莫耳之矽烷化合物的所有烷氧基中,所使用至少一僩選
1286155 六、申讀專利範圍 — 的Γ ΐ基氨氧化錄、脂環族有機胺和金屬氫氧化物所組成 、矢群之化合物的量為0.00 00 1至10 m〇l。 赤t如申請專利範圍第1項之薄膜成形用組成物,其pH為7 执更低。 ^如申請專利範圍第i項之薄膜成形用組成物,其中 械洛劑(B )包含以下列化學式(4 )所示之溶劑: R80(CHCH3CH20)eR9 (4 ) 和R9分別獨立地表示氛原子,或是選自具扪 二原^之燒基和CHJO—所組成的族群之單價有機基; 為1或2的整數。 且e 項一中種杯薄膜成形用方法,其包含將如申請專利範圍第! 加熱該所得塗層。 應用於基板上,然後 7· —種矽石基膜,係以如申請專利 形用方法所得到的。 和乾圍弟6項之薄臈成
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US4214057A (en) * | 1978-02-15 | 1980-07-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Coating composition for plastic substrates |
JPH0791509B2 (ja) * | 1985-12-17 | 1995-10-04 | 住友化学工業株式会社 | 半導体用絶縁膜形成塗布液 |
US5733644A (en) * | 1994-04-15 | 1998-03-31 | Mitsubishi Chemical Corporation | Curable composition and method for preparing the same |
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DE60117631D1 (de) | 2006-05-04 |
EP1146092A2 (en) | 2001-10-17 |
KR100739952B1 (ko) | 2007-07-16 |
KR20010100880A (ko) | 2001-11-14 |
JP4195773B2 (ja) | 2008-12-10 |
JP2001354904A (ja) | 2001-12-25 |
EP1146092B1 (en) | 2006-03-08 |
EP1146092A3 (en) | 2002-12-18 |
DE60117631T2 (de) | 2006-10-05 |
US6495264B2 (en) | 2002-12-17 |
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