WO2005068541A1 - 有機シリカ系膜の形成方法、有機シリカ系膜、配線構造体、半導体装置、および膜形成用組成物 - Google Patents
有機シリカ系膜の形成方法、有機シリカ系膜、配線構造体、半導体装置、および膜形成用組成物 Download PDFInfo
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- WO2005068541A1 WO2005068541A1 PCT/JP2005/000375 JP2005000375W WO2005068541A1 WO 2005068541 A1 WO2005068541 A1 WO 2005068541A1 JP 2005000375 W JP2005000375 W JP 2005000375W WO 2005068541 A1 WO2005068541 A1 WO 2005068541A1
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- Prior art keywords
- film
- forming
- organic silica
- based film
- bis
- Prior art date
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 153
- 239000000377 silicon dioxide Substances 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 239000004065 semiconductor Substances 0.000 title claims abstract description 28
- 238000000576 coating method Methods 0.000 claims abstract description 65
- 239000011248 coating agent Substances 0.000 claims abstract description 63
- 238000010894 electron beam technology Methods 0.000 claims abstract description 52
- 238000010438 heat treatment Methods 0.000 claims abstract description 29
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 29
- 239000011229 interlayer Substances 0.000 claims abstract description 14
- 230000001678 irradiating effect Effects 0.000 claims abstract description 14
- 229910000077 silane Inorganic materials 0.000 claims description 30
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 25
- 229920003257 polycarbosilane Polymers 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
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- -1 wiring structure Substances 0.000 description 84
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- 239000010936 titanium Substances 0.000 description 42
- 229910052719 titanium Inorganic materials 0.000 description 42
- 239000000243 solution Substances 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 29
- 229910052726 zirconium Inorganic materials 0.000 description 29
- 239000007983 Tris buffer Substances 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000005595 acetylacetonate group Chemical group 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical compound CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 13
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 229920001296 polysiloxane Polymers 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- HCOKJWUULRTBRS-UHFFFAOYSA-N propan-2-yloxysilane Chemical compound CC(C)O[SiH3] HCOKJWUULRTBRS-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- BVNZLSHMOBSFKP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxysilane Chemical compound CC(C)(C)O[SiH3] BVNZLSHMOBSFKP-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 229940022663 acetate Drugs 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000000962 organic group Chemical group 0.000 description 8
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 8
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 7
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
- 239000000010 aprotic solvent Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229920000620 organic polymer Polymers 0.000 description 6
- 238000001020 plasma etching Methods 0.000 description 6
- 239000010453 quartz Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
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- 229910003849 O-Si Inorganic materials 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- XWQLYVIMMBLXPY-UHFFFAOYSA-N butan-2-yloxysilane Chemical compound CCC(C)O[SiH3] XWQLYVIMMBLXPY-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
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- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 4
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- 150000001408 amides Chemical class 0.000 description 3
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- CMFFHNDRVNQUAX-UHFFFAOYSA-N dibutoxymethyl(dibutoxymethylsilylmethyl)silane Chemical compound CCCCOC(OCCCC)[SiH2]C[SiH2]C(OCCCC)OCCCC CMFFHNDRVNQUAX-UHFFFAOYSA-N 0.000 description 3
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
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- 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
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- ISSKPZWQMGEHLZ-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-pentacosafluorododecane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ISSKPZWQMGEHLZ-UHFFFAOYSA-M 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- MOOUPSHQAMJMSL-UHFFFAOYSA-N tert-butyl(trichloro)silane Chemical compound CC(C)(C)[Si](Cl)(Cl)Cl MOOUPSHQAMJMSL-UHFFFAOYSA-N 0.000 description 1
- MEZBMAOYBCEKPZ-UHFFFAOYSA-N tert-butyl(triiodo)silane Chemical compound CC(C)(C)[Si](I)(I)I MEZBMAOYBCEKPZ-UHFFFAOYSA-N 0.000 description 1
- YBCWQJZHAOTDLY-UHFFFAOYSA-N tert-butyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C(C)(C)C)OC1=CC=CC=C1 YBCWQJZHAOTDLY-UHFFFAOYSA-N 0.000 description 1
- HVEXJEOBOQONBC-UHFFFAOYSA-N tert-butyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C(C)(C)C HVEXJEOBOQONBC-UHFFFAOYSA-N 0.000 description 1
- ULXGRUZMLVGCGL-UHFFFAOYSA-N tert-butyl-tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C(C)(C)C ULXGRUZMLVGCGL-UHFFFAOYSA-N 0.000 description 1
- OQTSOKXAWXRIAC-UHFFFAOYSA-N tetrabutan-2-yl silicate Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)OC(C)CC OQTSOKXAWXRIAC-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 description 1
- 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
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- BCLLLHFGVQKVKL-UHFFFAOYSA-N tetratert-butyl silicate Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C BCLLLHFGVQKVKL-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- IVRXTRZVBJSOLZ-UHFFFAOYSA-N tri(butan-2-yloxy)-[2-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC=C1[Si](OC(C)CC)(OC(C)CC)OC(C)CC IVRXTRZVBJSOLZ-UHFFFAOYSA-N 0.000 description 1
- SGZJOYFOVHWDFY-UHFFFAOYSA-N tri(butan-2-yloxy)-[3-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC([Si](OC(C)CC)(OC(C)CC)OC(C)CC)=C1 SGZJOYFOVHWDFY-UHFFFAOYSA-N 0.000 description 1
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- MHQDJCZAQGWXBC-UHFFFAOYSA-N tri(butan-2-yloxy)-ethenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C=C MHQDJCZAQGWXBC-UHFFFAOYSA-N 0.000 description 1
- SGHZCASSRKVVCL-UHFFFAOYSA-N tri(butan-2-yloxy)-ethylsilane Chemical compound CCC(C)O[Si](CC)(OC(C)CC)OC(C)CC SGHZCASSRKVVCL-UHFFFAOYSA-N 0.000 description 1
- QWUMUNMNAGQTRJ-UHFFFAOYSA-N tri(butan-2-yloxy)-fluorosilane Chemical compound CCC(C)O[Si](F)(OC(C)CC)OC(C)CC QWUMUNMNAGQTRJ-UHFFFAOYSA-N 0.000 description 1
- RJNDDRZGJNVASH-UHFFFAOYSA-N tri(butan-2-yloxy)-methylsilane Chemical compound CCC(C)O[Si](C)(OC(C)CC)OC(C)CC RJNDDRZGJNVASH-UHFFFAOYSA-N 0.000 description 1
- PCDRXIBYKFIRQR-UHFFFAOYSA-N tri(butan-2-yloxy)-phenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC=C1 PCDRXIBYKFIRQR-UHFFFAOYSA-N 0.000 description 1
- ZARIZDBUWOPYMT-UHFFFAOYSA-N tri(butan-2-yloxy)-propylsilane Chemical compound CCC(C)O[Si](CCC)(OC(C)CC)OC(C)CC ZARIZDBUWOPYMT-UHFFFAOYSA-N 0.000 description 1
- JKJUOACCVYNCDI-UHFFFAOYSA-N tri(butan-2-yloxy)-tert-butylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C(C)(C)C JKJUOACCVYNCDI-UHFFFAOYSA-N 0.000 description 1
- HCSBZSDRJAJWHR-UHFFFAOYSA-N tribromo(butyl)silane Chemical compound CCCC[Si](Br)(Br)Br HCSBZSDRJAJWHR-UHFFFAOYSA-N 0.000 description 1
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- MHOVTIVXUNGWHW-UHFFFAOYSA-N tribromo(propan-2-yl)silane Chemical compound CC(C)[Si](Br)(Br)Br MHOVTIVXUNGWHW-UHFFFAOYSA-N 0.000 description 1
- RWRKNKVDHIEKHS-UHFFFAOYSA-N tribromo(propyl)silane Chemical compound CCC[Si](Br)(Br)Br RWRKNKVDHIEKHS-UHFFFAOYSA-N 0.000 description 1
- ASWZNPOTXAXUPB-UHFFFAOYSA-N tribromo(tribromosilyl)silane Chemical compound Br[Si](Br)(Br)[Si](Br)(Br)Br ASWZNPOTXAXUPB-UHFFFAOYSA-N 0.000 description 1
- PWVUSFVRYWVBDM-UHFFFAOYSA-N tribromo(tribromosilyloxy)silane Chemical compound Br[Si](Br)(Br)O[Si](Br)(Br)Br PWVUSFVRYWVBDM-UHFFFAOYSA-N 0.000 description 1
- IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
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- JXXQPVMVSMWLGZ-UHFFFAOYSA-N tributoxy(tributoxysilylmethyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C[Si](OCCCC)(OCCCC)OCCCC JXXQPVMVSMWLGZ-UHFFFAOYSA-N 0.000 description 1
- ZYXLOEAJFSQDQG-UHFFFAOYSA-N tributoxy-(2-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1[Si](OCCCC)(OCCCC)OCCCC ZYXLOEAJFSQDQG-UHFFFAOYSA-N 0.000 description 1
- YBNXDKRALACDIA-UHFFFAOYSA-N tributoxy-(4-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=C([Si](OCCCC)(OCCCC)OCCCC)C=C1 YBNXDKRALACDIA-UHFFFAOYSA-N 0.000 description 1
- JSQJUDVTRRCSRU-UHFFFAOYSA-N tributyl(chloro)silane Chemical compound CCCC[Si](Cl)(CCCC)CCCC JSQJUDVTRRCSRU-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CAPIMQICDAJXSB-UHFFFAOYSA-N trichloro(1-chloroethyl)silane Chemical compound CC(Cl)[Si](Cl)(Cl)Cl CAPIMQICDAJXSB-UHFFFAOYSA-N 0.000 description 1
- FMYXZXAKZWIOHO-UHFFFAOYSA-N trichloro(2-phenylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CCC1=CC=CC=C1 FMYXZXAKZWIOHO-UHFFFAOYSA-N 0.000 description 1
- WDVUXWDZTPZIIE-UHFFFAOYSA-N trichloro(2-trichlorosilylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC[Si](Cl)(Cl)Cl WDVUXWDZTPZIIE-UHFFFAOYSA-N 0.000 description 1
- SIPHWXREAZVVNS-UHFFFAOYSA-N trichloro(cyclohexyl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCCCC1 SIPHWXREAZVVNS-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- GPWLZOISJZHVHX-UHFFFAOYSA-N trichloro(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(Cl)Cl GPWLZOISJZHVHX-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 description 1
- QHAHOIWVGZZELU-UHFFFAOYSA-N trichloro(trichlorosilyloxy)silane Chemical compound Cl[Si](Cl)(Cl)O[Si](Cl)(Cl)Cl QHAHOIWVGZZELU-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-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
- GYTROFMCUJZKNA-UHFFFAOYSA-N triethyl triethoxysilyl silicate Chemical compound CCO[Si](OCC)(OCC)O[Si](OCC)(OCC)OCC GYTROFMCUJZKNA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- OWPIUELMEJJOEM-UHFFFAOYSA-N triiodo(2-phenylethyl)silane Chemical compound I[Si](I)(I)CCC1=CC=CC=C1 OWPIUELMEJJOEM-UHFFFAOYSA-N 0.000 description 1
- ARIHFGQDMNMGQJ-UHFFFAOYSA-N triiodo(methyl)silane Chemical compound C[Si](I)(I)I ARIHFGQDMNMGQJ-UHFFFAOYSA-N 0.000 description 1
- HBVCQKOZPHBDAR-UHFFFAOYSA-N triiodo(phenyl)silane Chemical compound I[Si](I)(I)C1=CC=CC=C1 HBVCQKOZPHBDAR-UHFFFAOYSA-N 0.000 description 1
- HWTOQUMCTOJBIS-UHFFFAOYSA-N triiodo(triiodosilylmethyl)silane Chemical compound I[Si](I)(I)C[Si](I)(I)I HWTOQUMCTOJBIS-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- KBFAHPBJNNSTGX-UHFFFAOYSA-N trimethoxy-(3-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC([Si](OC)(OC)OC)=C1 KBFAHPBJNNSTGX-UHFFFAOYSA-N 0.000 description 1
- YIRZROVNUPFFNZ-UHFFFAOYSA-N trimethoxy-(4-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=C([Si](OC)(OC)OC)C=C1 YIRZROVNUPFFNZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- RDDMOMIMRPHKSZ-UHFFFAOYSA-N trimethyl-(3-trimethylsilylphenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC([Si](C)(C)C)=C1 RDDMOMIMRPHKSZ-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
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- DMFPULBEKRWMBR-UHFFFAOYSA-N tris(3-bicyclo[2.2.1]heptanyl)-chlorosilane Chemical compound C1C(C2)CCC2C1[Si](Cl)(C1C2CCC(C2)C1)C1C(C2)CCC2C1 DMFPULBEKRWMBR-UHFFFAOYSA-N 0.000 description 1
- BNCOGDMUGQWFQE-UHFFFAOYSA-N tris(ethenyl)silicon Chemical compound C=C[Si](C=C)C=C BNCOGDMUGQWFQE-UHFFFAOYSA-N 0.000 description 1
- ZZEMYLNHCSTIPH-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C ZZEMYLNHCSTIPH-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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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- 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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- 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
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- 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
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- the present invention relates to a method for forming an organic silica-based film, an organic silica-based film, a wiring structure, a semiconductor device, and a film-forming composition.
- CVD Chemical Vapor
- a silica (SiO 2) film formed by a vacuum process such as a deposition method is often used.
- a coating-type insulating film called a SOG (Spin on Glass) film which is mainly composed of a hydrolysis product of tetraalkoxylan. It has become.
- an interlayer insulating film having a low relative dielectric constant which is mainly composed of polyorganosiloxane and is called organic SOG, has been developed.
- the formed insulating film is subjected to various plasma etching and chemical treatment during processing. Even though the resulting insulating film has a low dielectric constant and a high mechanical strength, it has a problem that the plasma etching resistance and the RIE resistance are not sufficient.
- Plasma damage that occurs during processing of an insulating film is mainly caused by radicals generated by plasma extracting CH from the Si-CH structure of polysiloxane.
- silanol groups Reacts quickly with oxygen atoms and oxygen radicals, and further draws in hydrogen, converting it to silanol groups (Si-OH).
- the presence of the silanol group increases the hygroscopicity of the insulating film, causing an increase in the relative dielectric constant, a deterioration in chemical resistance, and a decrease in electrical insulation.
- polycarbosilane itself or a composition obtained by mixing polysiloxane and polycarbosilane has been proposed (Japanese Patent Application Laid-Open No. H10-163,837).
- This composition is intended to improve heat resistance and hygroscopic resistance.
- Such a material when having a Si-OH structure in polycarbosilane, has steric hindrance and Si-CH
- this Si—OH structure is considered to be less reactive than the Si OH group in the polysiloxane unit, making it difficult to form a sufficiently high condensation state by heating. OH groups remain in the resulting insulating film, which does not result in excellent plasma resistance or chemical resistance.
- Patent Document 1 JP 2001-127152 A
- Patent Document 2 JP 2001-286821 A
- Patent Document 3 US Patent No. 6042994
- Patent Document 4 U.S. Pat.No. 6,204,201
- the present invention provides a method for efficiently coating a film at a lower electron beam irradiation amount and in a shorter time and at a lower temperature. It can be cured and can be suitably used as an interlayer insulating film in, for example, semiconductor devices.It has a small relative dielectric constant and has excellent mechanical strength and adhesion, as well as excellent plasma resistance and chemical resistance. It is an object of the present invention to provide a method for forming an organic silica-based film capable of forming a thin film, and a film-forming composition used in the method.
- Another object of the present invention is to provide an organic silica-based film obtained by the method for forming an organic silica-based film of the present invention, a wiring structure including the organic silica-based film, and a semiconductor including the wiring structure. It is to provide a device.
- the method for forming an organic silica-based film of the present invention comprises:
- Coatings consisting of silicon compounds having Si O Si structure and Si—CH—Si structure
- the silicon compound has a Si—O—Si—structure and a—Si—CH—Si—structure——Si—O—Si— / —Si— CH—Si—
- the carbon content in the silicon compound may be 13 to 24 mol%.
- the silicon compound may be:
- It can be a hydrolyzed condensate obtained by hydrolyzing and condensing (B) a hydrolyzable group-containing silane monomer in the presence of (A) polycarbosilane.
- the electron beam is irradiated with an electron beam at an accelerating voltage of 0.1 to 20 keV, and the electron beam is irradiated.
- the amount can be as low as 1000 ⁇ C / cm 2 .
- heating and irradiation with an electron beam can be performed simultaneously.
- the heating can be performed at 300 to 450 ° C.
- the irradiation with the electron beam is performed. It can be performed in the absence of oxygen.
- the organic silica-based film of the present invention is obtained by the method for forming an organic silica-based film of the present invention, and has a relative dielectric constant of 1.5-3.5 and a film density of 0.7-1. 3gZcm 3 .
- the wiring structure of the present invention uses the above-mentioned organic silica-based film of the present invention as an interlayer insulating film.
- a semiconductor device according to the present invention includes the wiring structure according to the present invention.
- the film-forming composition of the present invention comprises:
- the hydrolysis-condensation product in the film forming composition of the present invention, can be 13 24 mole 0/0 containing TansoHara child.
- the above-mentioned (B) is added to the above-mentioned (B) with respect to 100 parts by weight of the above-mentioned component (A) in terms of a completely hydrolyzed condensate of the (A) component.
- the ingredients can be one to one thousand parts by weight.
- the contents of sodium, potassium, and iron may each be 100 ppb or less.
- a step of forming a coating film made of the silicon compound on a substrate a step of heating the coating film, and an electron beam
- a step of performing a curing treatment by irradiating the coating film with a lower electron beam irradiation amount whereby the coating film can be efficiently cured at a lower temperature in a shorter time.
- FIG. 1 is a diagram showing IR ⁇ vectors of the silica-based films obtained in Example 2 and Comparative Example 2, respectively.
- the method for forming an organic silica-based film according to the present invention comprises a Si O Si structure and Si—CH—Si—
- a silicon compound having a structure hereinafter, also simply referred to as a “silicon compound!”
- a step of forming a coating film on a substrate a step of heating the coating film, Performing a hardening treatment by irradiating an electron beam.
- a coating film made of an elemental compound is formed on a substrate.
- the Si O Si structure in the silicon compound Z Si—CH—Si structure (model 1)
- the number of moles of the Si O Si structure in the present invention is based on the assumption that the total amount of the hydrolyzable silane monomer used is hydrolyzed and condensed in a silicon compound composed of a hydrolyzed condensate described later. This is the number of moles assuming that Si— CH— Si
- the number of moles of the structure is the number of moles of the —Si 2 O—Si structure present in the polycarbosilane described below.
- the carbon atom concentration in the coating film which is also a silicon compound, is 13 to 24 mol%. If the carbon atom concentration in the silicon compound is less than 13 mol%, the resulting film may not have sufficient plasma resistance and chemical solution resistance, while if it exceeds 24 mol%, the resulting film may have an interlayer resistance. In some cases, the balance of characteristics as an insulating film is lacking.
- the carbon atom concentration in the silicon compound-based coating film is determined by the amount of the hydrolyzed condensate obtained when all of the hydrolyzable silane monomers described below are hydrolyzed and condensed. It is the amount of carbon atoms in a silicon compound.
- the film thickness of the coating film which can also be a silicon compound, is usually 112 nm, preferably 10 nm to 1,000 nm.
- the coating film having the capability of a silicon compound may be formed by applying a solution obtained by dissolving a polymer in an organic solvent and drying, or by a CVD method or the like.
- a film obtained by applying the film-forming composition described below to a substrate and drying the composition is preferred.
- the film-forming composition for forming a coating film composed of a silicon compound is preferably one containing polycarbosilane and polysiloxane as a polymer component.
- the film-forming composition of the present invention can be produced by dissolving polycarbosilane and polysiloxane in an organic solvent, and particularly, (A) polycarbosilane (hereinafter also referred to as “component (A)”). ) In the presence of (B) a hydrolyzable condensate obtained by hydrolyzing and condensing a hydrolyzable group-containing silane monomer (hereinafter, also referred to as “(B) component! / ⁇ ⁇ )” (hereinafter simply referred to as “hydrolysis”). The condensate is also preferably obtained by dissolving U) in an organic solvent.
- the term "hydrolyzable group” refers to a group that can be hydrolyzed by carohydrate during production of the film-forming composition of the present invention.
- Specific examples of the hydrolyzable group include, but are not particularly limited to, a halogen atom, a hydroxy group, an alkoxy group, a sulfone group, a methanesulfone group, and a trifluoromethanesulfone group.
- the weight average molecular weight (Mw) of the hydrolyzed condensate in terms of polystyrene is 1,500-500,000, a force S is preferred ⁇ , 2,000-200,000, a force S is preferred over ⁇ 2. , 000—100, 000 is more preferable. If the weight average molecular weight in terms of polystyrene of the hydrolysis condensate is less than 1,500, the desired relative dielectric constant may not be obtained.On the other hand, if it exceeds 500,000, the in-plane uniformity of the coating film may be reduced. May be inferior.
- the mixing ratio of the component (A) and the component (B) is such that (B) The ingredients are 1 to 1000 parts by weight More preferably, it is 5 to 100 parts by weight, more preferably 5 to 20 parts by weight. When the amount of the component (B) is less than 1 part by weight, sufficient chemical solution resistance may not be exhibited after film formation, and when it exceeds 1000 parts by weight, a low dielectric constant may not be achieved. is there.
- the (A) polycarbosilane as the component (A) is, for example, a polycarbosilane conjugated product represented by the following general formula (1) (hereinafter, also referred to as “I conjugated product 1”). ).
- R represents a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, an acyloxy group, a sulfone group, a methanesulfone group, a trifluoromethanesulfone group, an alkyl group, an aryl group, an aryl group, and a glycidyl group.
- R 9 represents a halogen atom, a hydroxy group, an alkoxy group, an acyloxy group, a sulfone group, a methanesulfone group, a trifluoromethanesulfone group, an alkyl group, an aryl group, an aryl group, and a glycidyl group.
- R 10 and R 11 are the same or different and each represents a halogen atom, a hydroxy group, an alkoxy group, an acyloxy group, a sulfone group, a methanesulfone group, a trifluoromethanesulfone group, a C 2-6 A group selected from the group consisting of an alkyl group, an aryl group, an aryl group, and a glycidyl group.
- R 12 — R 14 are the same or different and represent a substituted or unsubstituted methylene group, alkylene group, alkenyl group, alkyl group, arylene group, and X, y, and z represent 0-10, respectively.
- the alkylene group may be an ethylene group, a propylene group, a butylene group, or the like.
- Xylene groups, decylene groups and the like are preferred, and preferably have 2 to 6 carbon atoms.
- These alkylene groups may be chain-like or branched, or may further form a ring. It may be replaced by an atom or the like.
- examples of the alkenyl group include an eturene group, a probenylene group, a 1-butylene group, a 2-butylene group, and the like.
- a hydrogen atom may be substituted by a fluorine atom or the like.
- alkynyl group include an acetylene group and a propylene group.
- arylene group include a phenylene group and a naphthylene group, and a hydrogen atom may be substituted with a fluorine atom or the like.
- R 8 to R 11 may be the same or different groups.
- X, y, and z are 0 ⁇ x ⁇ 800, 0 ⁇ y ⁇ 500, and 0 ⁇ 1,000, respectively, and more preferably, 0 ⁇ x ⁇ 500, 0 ⁇ y ⁇ 300, 0 ⁇ z ⁇ 500, and more preferably 0 ⁇ x ⁇ 100, 0 ⁇ y ⁇ 50, and 0 ⁇ z ⁇ 100.
- the compound represented by the general formula (1) includes, for example, chloromethyltrichlorosilane, bromomethinoletrichlorosilane, chloromethinolemethinoresichlorosilane, chloromethinoleetinoresichlorosilane, chloromethylvinyldichlorosilane, Chloromethylphenyldichlorosilane, bromomethylmethyldichlorosilane, bromomethylvinyldichlorosilane, chloromethyldimethylchlorosilane, chloromethyldivinylchlorosilane, bromomethyldimethylchlorosilane, (1-chloroethyl) trichlorosilane, (1chloropropylpropyl) trichlorosilane Chlorosilane, chloromethyltrimethoxysilane, bromomethyltrimethoxysilane, chloromethyldimethoxysilane, chloro
- the reaction can be carried out in the presence of at least one of an alkali metal and an alkaline earth metal, and if necessary, further treated with an alcohol, an organic acid, a reducing agent or the like.
- alkali metal Li, Na, and K are preferable, and as the alkaline earth metal, Mg and the like are preferable.
- the hydrolyzable group-containing silane monomer (B) is not particularly limited as long as it is a silane monomer having a hydrolyzable group.
- a compound represented by the following general formula (2) Group of the compound represented by the following general formula (3) (hereinafter, also referred to as "compound 3"). At least one selected silanied compound may be used. it can be used.
- R 1 represents a hydrogen atom, a fluorine atom or a monovalent organic group
- X represents a halogen atom or an alkoxy group
- a represents an integer of 0-3.
- R 2 and R 3 are the same or different and each represents a monovalent organic group
- b and c are the same or different and represent an integer of 0-2
- R 4 is an oxygen atom or a phenylene group.
- e represents an integer of 16
- Y and Z are the same or different and represent a halogen atom or an alkoxy group
- d represents 0 or 1.
- examples of the halogen atom represented by X and Y include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- R in the alkoxy group (one OR) represented by Y in the general formula (3) the same as the alkyl group and aryl group of R 1 to R 4 described later can be exemplified.
- R 1 is a hydrogen atom, a fluorine atom or a monovalent organic group.
- the monovalent organic group include an alkyl group, an alkenyl group, an aryl group, an aryl group and a glycidyl group.
- R 2 is preferably a monovalent organic group, particularly an alkyl group or a phenyl group.
- the alkyl group includes a methyl group, an ethyl group, a propyl group, a butyl group and the like, and preferably has 115 carbon atoms.
- These alkyl groups may be chain-like or branched, and a hydrogen atom may be substituted with a fluorine atom, an amino group, or the like.
- alkyl group examples include a butyl group, a probel group, a 3-butyr group, and a 3-pentyl group.
- aryl group examples include a phenyl group, a naphthyl group, a methylphenyl group, an ethylphenyl group, a chlorophenyl group, a bromophenyl group, a fluorophenyl group and the like.
- hydrocarbon moiety of the alkoxy group for X those listed as monovalent organic groups of can be applied as they are.
- compound 2 Specific examples of the compound represented by the general formula (2) (hereinafter, also referred to as “compound 2”) include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-iso-propoxysilane, n-butoxysilane, tetra-sec-butoxysilane, tetra-tert-butoxysilane, tetraphenoxysilane, trimethoxysilane, triethoxysilane, tree n-propoxysilane, tree iso-propoxysilane, tree n-butoxysilane, tri — Sec—butoxy silane, tree tert-butoxy silane, triphenoxy silane, fluorotrimethoxy silane, fluoro triethoxy silane, fluoro n-propoxy silane, fluoro iso iso-propoxy silane, fluoro n-butoxy silane, fluoro
- Compound 2 is preferably methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltriiso-propoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, vinyltriethoxysilane.
- examples of the monovalent organic group represented by R 2 and R 3 include the same organic groups as those in the general formula (2).
- Kisaetokishiji R 4 is The compound of oxygen atoms, the hexa chloro disiloxane, to hexa bromo disiloxane, to Kisayo one de Siji siloxane, to hexa methoxy disiloxane, to Siloxane, hexaphenoxydisiloxane, 1,1,1,3,3-pentamethoxy-3-methyldisiloxane, 1,1,1,3,3-pentaethoxy-3-methyldisiloxane, 1, 1, 1 , 3,3-pentaphenoxy-3-methyldisiloxane, 1,1,1,3,3-pentamethoxy-3-ethyldisiloxane, 1,1,1,3,3-pentaethoxy-3-ethylethylsiloxane, 1,1,1,3,3-pentaphenoxy-3-ethyldisiloxane, 1,1,1,3,3-pentam
- compounds where d is 0 include hexachlorodisilane, hexabromodisilane, hexiodosidisilane, hexamethoxydisilane, hexethoxydisilane, Hexaphenoxydisilane, 1,1,1,2,2-pentamethoxy-1-methyldisilane, 1,1,1,2,2-pentaethoxy-1-methyldisilane, 1,1,1, 2, 2-pentaphenoxy —2-Methyldisilane, 1,1,1,2,2-pentamethoxy—2-ethylethylsilane, 1,1,1,2,2-pentaethoxy-2-ethyldisilane, 1,1,1,2,2 —Pentaphenoxy 2-ethyldisilane, 1,1,1,2,2-pentamethoxy—2-phenyldisilane, 1,1,1,2,2-pentaethoxy-2-phenyldisilane, 1, 1
- At least one type of the silani conjugate selected from the group of the compounds 2 and 3 is hydrolyzed and condensed. It is preferred to use more than 0.5 mol and not more than 150 mol of water per 1 mol of the compounds 2 and 3. It is particularly preferable to remove more than 0.5 mol and not more than 130 mol of water.
- hydrolyzed condensate of the present invention can be obtained by hydrolyzing and condensing the component (A) in the presence of the component (B).
- component (A) can be hydrolyzed while component (A) and component (B) are dissolved in an organic solvent.
- organic solvent examples include methanol
- the reaction temperature in the hydrolytic condensation is 0 to 100 ° C, preferably 20 to 60 ° C, and the reaction time is 30 minutes to 24 hours, preferably 1 hour to 8 hours.
- a specific catalyst can be used when the component (B) is hydrolyzed and condensed in the presence of the component (A) in order to produce a hydrolyzed condensate.
- the catalyst at least one selected from the group consisting of an alkali catalyst, a metal chelate catalyst, and an acid catalyst can be used.
- alkaline catalyst examples include sodium hydroxide, potassium hydroxide, lithium hydroxide, pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, monoethanolamine, diethanolamine, dimethyl.
- Monoethanolamine monomethyl ethanolamine, triethanolamine, diazabicyclooctane, diazabicyclononane, diazabicycloundecene, tetramethylammonium-dimethylhydroxide, tetraethylammonium-dimethylhydroxide, tetrapropylammonium Demoxide mouth oxide, tetrabutylammonium-Demoxide mouth oxide, ammonia, methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, pentylamine, octylamine, noni N, N-Dimethylamine, N, N-Diethylamine, N, N-Dipropylamine, N, N-Dibutylamine, Trimethylamine, Triethylamine, Tripropylamine, Tributylamine, Cyclohexylamine, Trimethylylamine Examples include midine, 1-amino
- these alkali catalysts may be used simultaneously.
- metal chelate catalyst for example, triethoxy mono (acetyl acetatetonate) titanium Tri-propoxy 'mono (acetyl acetate toner) titanium, tri-propoxy' mono (acetyl acetate toner) titanium, tri-n-butoxy.
- Aluminum chelates such as tris (acetylacetonato) anoremium and tris (ethylinoacetoacetate) anoremini;
- a chelate conjugate of titanium or aluminum particularly preferably a chelate of titanium.
- metal chelate catalysts may be used simultaneously.
- Examples of the acid catalyst include inorganic acids such as hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, and boric acid; acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, Nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacic acid, gallic acid, butyric acid, melitic acid, arachidonic acid, shikimic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, Linoleic acid, linoleic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, ⁇ -toluenesulfonic acid, benzenesulfonic acid, monochloroacetic acid, dichloro
- the amount of the catalyst to be used is generally 0.0001-10 mol, preferably ⁇ 0.00000, relative to 1 mol of the total amount of the groups represented by X, ⁇ , and Z in compounds 2 and 3. — 5 moles.
- the temperature at which the compounds 2 and 3 are hydrolyzed is generally 0 to 100 ° C, preferably 15 to 80 ° C.
- complete 311 hydrolyzed condensate refers to (A) a polycarbosilane and a hydrolyzable group in compounds 2 and 3 which are hydrolyzed 100% to form SiOH groups, and To form a siloxane structure by condensation.
- the hydrolyzed condensate is preferably (A) a hydrolyzed condensate of polycarbosilane and compound 2 from the viewpoint that the storage stability of the obtained composition is more excellent.
- the amount of compound 2,3 used for (A) polycarbosilane is preferably 500-4000 parts by weight of the total amount of compound 2,3 per 100 parts by weight of (A) polycarbosilane, more preferably ⁇ 1000. — 3000 parts by weight.
- the hydrolyzed condensate and, if necessary, other components described later can be dissolved or dispersed in an organic solvent.
- the organic solvent used as a component of the film-forming composition of the present invention is not particularly limited as long as it can be removed before a final film is obtained. More specifically, a protic solvent And aprotic solvents.
- the protic solvent include alcohol solvents.
- the aprotic solvent include ketone solvents, ester solvents, ether solvents, amide solvents, and other aprotic solvents described below.
- the alcohol solvent includes methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-pentanol, i-pentanol, and 2-methylbutanol.
- Ethylene glycolone 1,2-propylene glycol, 1,3-butylene glycol, 2,4-pentanediol, 2-methyl-2,4 pentanediol, 2,5 xanediol, 2,4 heptanediol, 2-ethyl-1, 3
- Polyhydric alcohol solvents such as xanediol, diethylene glycol, dipropylene glycol, triethylene glycol, and tripropylene glycol;
- Ethylene glycolone monomethinoleatene Ethylene glycolone monopropineleatene, Ethylene glycolone monopropineleatene, Ethylene glycolone monobutineoleatene, Ethylene glycolone monohexenolate, ethylene glycolone monofe-noreatenone
- Ethylene glycolone mono-2-ethylbutylenole ether diethylene glycolone monomethylenolate, diethylene glycolone monoethylenoate, diethylene glycolone monolipe pinoleate enole, diethylene glycolone monobutylinoleatene, diethylene glycolone Lemonohexyl ether, propylene glycol monomethyl ether, propylene glycol monoethenolate ether, propylene glycol monopropinolate ether, propylene glycol monomonobutynole ether, dipropylene glycol monomethinole ether, dipropylene glycol Polyhydric alcohol partial ether solvents such as monoethyl ether and dipropylene glycol monopropyl ether;
- One or more of these alcohol solvents may be used at the same time.
- Ketone solvents include acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, getyl ketone, methyl i-butyl ketone, methyl n-pentyl ketone, ethyl n-butyl ketone, methyl n-xyl ketone, and di-butyl ketone.
- One or more of these ketone solvents may be used simultaneously.
- amide solvents examples include formamide, N-methylformamide, N, N-dimethylformamide, N-ethylformamide, N, N-getylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide , N-Ethylacetamide, N, N-Getylacetamide, N-methylpropionamide, N-methylpyrrolidone, N-formylmorpholine, N-formylpiperidine, N-formylpyrrolidine, N-acetylmorpholine, N-acetylpi Lysine, N-acetylpyrrolidine and the like. There is one kind of these amide solvents Or you may use two or more at the same time.
- ester solvent examples include getyl carbonate, ethylene carbonate, propylene carbonate, getyl carbonate, methyl acetate, ethyl acetate, ⁇ -butyrolataton, ⁇ -valerolatone, ⁇ -propyl acetate, i-propyl acetate, n-butyl acetate, and acetic acid.
- aprotic solvents examples include acetonitrile, dimethyl sulfoxide, N, N, ⁇ ', ⁇ '-tetraethylsulfamide, hexamethylphosphoric triamide, ⁇ ⁇ ⁇ methylmorpholone, ⁇ -methyl propyl pyrrole, ⁇ -ethylpyrrole , ⁇ -methyl- ⁇ -pyrroline, ⁇ -methylpiperidine, ⁇
- ketone solvents such as 2-heptanone, methyl isobutyl ketone, getyl ketone, and cyclohexanone are preferred, and propylene glycol monopropyl ether is preferred as the alcohol solvent.
- the total solid concentration of the film-forming composition of the present invention thus obtained is preferably 2 to 30% by weight, and is appropriately adjusted depending on the purpose of use. When the total solid concentration of the film-forming composition is 2 to 30% by weight, the thickness of the coating film is in an appropriate range, and the storage stability is more excellent. The adjustment of the total solid content concentration is performed, if necessary, by concentration and dilution with the organic solvent.
- the film-forming composition of the present invention may not contain a reaction accelerator for promoting the hydrolysis reaction and the Z or condensation reaction of the component (A) and the Z or the component (B).
- reaction accelerator refers to any one of a reaction initiator, a catalyst (acid generator, base generator) and a sensitizer having an electron beam absorption function, or a combination of two or more of these. means.
- a silica film cured using an acid generator or a base generator generally has a large amount of residual silanol and high hygroscopicity, and as a result, becomes a film having a high dielectric constant. Further, in the composition containing these acid generators and base generators, the acid generators and base generators themselves, and the acid and basic substances generated from these, serve as charge carriers, impairing the insulating properties of the film, and In some cases, such as deterioration of wiring metal, the quality as an insulating film of an LSI semiconductor device that requires high insulation reliability may not be satisfied.
- the coating film can be cured through the heating step and the electron beam irradiation step without including such a reaction accelerator. Therefore, these problems can be avoided.
- the contents of sodium, potassium, and iron are desirably 100 ppb or less. Since these elements serve as a contamination source of the semiconductor device, it is desirable that these elements be eliminated from the film forming composition of the present invention as much as possible.
- the film-forming composition of the present invention may further contain components such as an organic polymer, a surfactant, and a silane coupling agent. Further, these additives may be added to a solvent in which each component is dissolved or dispersed before manufacturing the film-forming composition.
- the organic polymer used in the present invention is easy to form pores in a silica-based film. It can be added as a dissolving component.
- the addition of such an organic polymer is described in JP-A-2000-290590, JP-A-2000-313612, Hedrick, JL, et al.
- organic polymer examples include a polymer having a sugar chain structure, a vinylamide polymer,
- the surfactant examples include a nonionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, and the like. Further, a fluorine-based surfactant, a silicone-based surfactant, Examples thereof include a polyalkylene oxide-based surfactant and a poly (meth) atalylate-based surfactant.
- fluorine-based surfactant examples include 1,1,2,2-tetrafluorooctyl (1,1,2,2-tetrafluoropropyl) ether and 1,1,2,2-tetrafluorocarbon Octylhexyl ether, octaethylene glycol di (1,1,2,2-tetrafluorobutyl) ether, hexethylene glycol (1,1,2,2,3,3-hexafluoropentyl) ether, Octapropylene glycol di (1,1,2,2-tetrafluorobutyl) ether, hexapropylene glycol di (1,1,2,2,3,3-hexafluoropentyl) ether, perfluorododecyl sulfonate Sodium, 1, 1, 2, 2, 8, 8, 9, 9, 10, 10—decaf mouth rhododecane, 1, 1, 2, 2, 3, 3—hexafluorodecane, N— [3— (perfluo Loocta
- silicone-based surfactant for example, SH7PA, SH21PA, SH30PA, ST94PA [the deviation is also manufactured by Dow Kojung Silicone Toray] can be used.
- SH28PA and SH30PA are particularly preferable.
- the amount of the surfactant used is usually 0.000001 to 11 parts by weight based on 100 parts by weight of the film-forming composition. These may be used alone or in combination of two or more.
- silane coupling agent examples include 3-glycidyloxypropyltrimethoxysilane, 3-aminoglycidyloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, 1 -Methacryloxypropyl methinoresimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 2-aminopropyltrimethoxysilane, 2-aminopropyltriethoxysilane, N- (2- (Aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3aminopropylmethyldimethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ure
- the method for forming an organic silica-based film of the present invention includes the steps of forming a coating film having a silicon compound power on a substrate, heating the coating film, and applying an electron beam to the coating film. Irradiating and performing a curing treatment.
- the step of heating the coating film and the step of irradiating the coating film with an electron beam may be performed simultaneously.
- the curing treatment of the present invention by simultaneously performing heating and electron beam irradiation, the condensation reaction of the organic silica sol can be sufficiently achieved at a relatively low temperature and in a short time with a smaller amount of electron beam irradiation.
- the organic silica-based film intended for the invention can be obtained.
- the curing treatment can be performed preferably for 30 seconds to 10 minutes, more preferably for 30 seconds to 7 minutes.
- an organic silica-based film of the present invention when forming a coating film composed of a silicon compound, a coating method such as spin coating, dipping, roll coating, or spraying is used.
- the substrate to be applied is not particularly limited, and examples thereof include Si-containing layers such as Si, SiO, SiN, SiC, SiCN, and SiON. Specific as base material
- a semiconductor substrate made of the above material may be used.
- the formed coating film is then dried at room temperature or heated at a temperature of about 80-600 ° C, usually for about 5-240 minutes, and dried to form a glassy or macromolecular coating. Can be formed.
- a hot plate, an oven, a furnace, or the like may be used as a heating method at this time.
- the heating can be performed under air, a nitrogen atmosphere, an argon atmosphere, a vacuum, a reduced pressure with controlled oxygen concentration, or the like.
- the energy (acceleration voltage) when irradiating an electron beam is 0.1 to 20 keV, and the amount of electron beam irradiation is 11/1000 C / cm 2 (preferably 1 0-500 CZcm 2 , more preferably 10-300 CZcm 2 ).
- the acceleration voltage is 0.1 to 20 keV, the electron beam can sufficiently penetrate into the coating film without penetrating the film and damaging the underlying semiconductor element.
- the electron beam irradiation amount is 11 to 1000 C / cm 2 , the entire coating film can be reacted, and damage to the coating film can be reduced.
- the heating temperature of the substrate at the time of electron beam irradiation is usually 300 to 450 ° C. If the heating temperature is lower than 300 ° C, the mobility of the molecular chains in the organic silica sol is not activated, and a sufficiently high condensation rate cannot be obtained. When the heating temperature is higher than 450 ° C, molecules in the organic silica sol are easily decomposed. On the other hand, if the heating temperature is higher than 450 ° C., it will not be compatible with the steps in the semiconductor device manufacturing process, for example, the copper damascene process usually performed at 450 ° C. or lower.
- a hot plate, infrared lamp annealing, or the like can be used as a means for heating simultaneously with electron beam irradiation.
- the time required for the coating to be cured by electron beam irradiation is about 1 minute to 5 minutes, which is significantly shorter than the 15 minutes and 12 hours required for thermal curing. For this reason, it can be said that electron beam irradiation is suitable for wafer-by-wafer processing.
- the coating film of the present invention was heat-cured in advance with the substrate heated to 250 ° C. to 500 ° C.
- the organic silica-based film may be irradiated with an electron beam.
- the film in order to control the curing speed of the coating film, if necessary, the film may be heated stepwise, or may be heated to an atmosphere such as nitrogen, air, oxygen, or a reduced pressure. Or you can choose.
- the curing treatment of the coating film of the present invention can be performed under an inert atmosphere or under reduced pressure.
- the absence of oxygen means that the oxygen partial pressure is preferably 0.1 lkPa or less, more preferably 0.1 OlkPa or less.
- electron beam irradiation may be performed in an inert gas atmosphere.
- the inert gas used is N, He, Ar, Kr and Xe, preferably He and Ar
- the film is oxidized and the dielectric constant of the obtained coating film can be maintained.
- the electron beam irradiation may be performed under a pressurized or reduced pressure atmosphere.
- the pressure at that time is preferably 0.001 to 1000 kPa, more preferably 0.001 to 101.3 kPa. If the pressure is out of the above range, in-plane non-uniformity of the degree of curing may occur. Further, in order to control the curing speed of the coating film, if necessary, heating may be performed stepwise, or an inert gas such as nitrogen, or an atmospheric condition such as a reduced pressure state may be selected.
- the method includes the steps of heating a coating film made of a silicon compound and irradiating the coating film with an electron beam to perform a curing treatment.
- the coating can be cured in a shorter time and at a lower temperature with a smaller amount of electron beam irradiation.
- the organic silica-based film of the present invention is obtained by the above-described method for forming an organic silica-based film of the present invention.
- the carbon content (number of atoms) is 13 to 24 mol%, preferably in the range of 13 to 20 mol%.
- the carbon content is within the above range, curing can be performed with a smaller amount of electron beam irradiation, and mechanical strength can be improved while maintaining a low dielectric constant of the obtained organic silica-based film. . 13 mol% carbon content If the amount is smaller, the diffusion barrier in the solid-state reaction will be high. The reaction will not be accelerated even when irradiated with an electron beam. On the other hand, if the carbon content is more than 24 mol%, the mobility of the molecule will be too high and the elastic modulus will be too high. In some cases, the film exhibits a glass transition point, which is not preferable.
- the organic silica-based film of the present invention has a low dielectric constant with extremely high elastic modulus and film density, as is clear from the examples described later. More specifically, the film density of the organic silica-based film of the present invention is usually 0.7 to 1.3 gZcm 3 , preferably 0.7 to 1.2 g / cm 3 , and more preferably 0.7 to 0.7 g / cm 3 . 1. is a OgZcm 3. If the film density is less than 0.7 gZcm 3 , the mechanical strength of the coating film will decrease, while if it exceeds 1.3 gZcm 3 , a low dielectric constant cannot be obtained.
- the relative dielectric constant of the organic silica-based film of the present invention is usually 1.5-3.5, preferably 1.9-3.1, and more preferably 2.0-3.0. From these facts, it can be said that the organic silica-based film of the present invention has extremely excellent insulating film properties such as mechanical strength and relative dielectric constant.
- the organic silica-based film of the present invention has a water contact angle of preferably 60 ° or more, more preferably 70 ° or more. This indicates that the organic silica-based film of the present invention is hydrophobic, and can maintain a low relative dielectric constant with low hygroscopicity. Further, such an organic silica-based film is less susceptible to damage by RIE used in a semiconductor process due to its low hygroscopicity, and is also excellent in chemical resistance to a wet cleaning solution. In particular, this tendency is remarkable in an organic silica-based film having a porous structure in which the insulating film itself has a relative dielectric constant k of 2.5 or less.
- the organosilica-based film of the present invention As described above, the organosilica-based film of the present invention
- the silicon compound has a specific composition and carbon content, it has excellent insulating film properties such as relative dielectric constant, elastic modulus, plasma resistance, and chemical resistance, and can be formed at low temperature and in a short time.
- the film-forming composition of the present invention used for forming a coating film comprises an ionic substance such as an electron beam-active acid generator, a base generator, or a sensitizer; a charge carrier; It does not need to include the source of matter, so it must not contain contaminants in semiconductor devices.
- the organic silica-based film of the present invention has low relative dielectric constant, excellent mechanical strength and adhesiveness, and excellent plasma resistance and chemical resistance, so that it can be used for LSI, system LSI, DRAM, SDRAM. , RDRAM, D—Interlayer insulating film for semiconductor devices such as RDRAM, etching stopper film, protective film such as surface coat film of semiconductor device, intermediate layer in semiconductor manufacturing process using multilayer resist, interlayer insulating film for multilayer wiring board It can be suitably used for applications such as a protective film and an insulating film for a liquid crystal display element. Further, the organic silica-based film of the present invention can be suitably used for a semiconductor device including a wiring structure such as a copper damascene wiring structure.
- Sample Prepared by dissolving polymer lg in lOOcc of tetrahydrofuran using tetrahydrofuran as a solvent.
- Standard polystyrene Standard polystyrene manufactured by Pressure Chemika Nore in the United States was used.
- Equipment High-temperature high-speed gel permeation chromatogram (Model 150—C ALC / GPC) manufactured by Waters, USA
- the relative permittivity at 200 ° C was measured in the same manner as in 2.1.2, and the difference from the relative permittivity in 2.1.2 was shown.
- the obtained polymer film was measured by SAW (Surface Acoustic Wave) method.
- the relative dielectric constant of the film was measured, and the film was rated according to the value of the relative dielectric constant that increased before and after the plasma irradiation.
- the cured organic silica film was immersed in a triethanolamine aqueous solution of pH 12 at room temperature for 10 minutes, washed with water, and water droplets on the surface were dried by nitrogen blow, and then the relative dielectric constant was measured, which increased before and after the test. It was rated according to the value of the relative permittivity.
- composition A containing a hydrolyzed condensate of —Si (molar ratio) 0.034 was obtained.
- the composition for forming a film (hereinafter, simply referred to as “composition”) has a sodium content of 0.5 ppb, a potassium content of 0.8 ppb, and an iron content. It was 7ppb.
- Film-forming composition B containing 0.153 hydrolyzed condensate was obtained.
- This composition B had a sodium content of l. Lppb, a potassium content of 0.4 ppb, and an iron content of 0.6 ppb.
- reaction solution was cooled to room temperature. Evaporation of 272 g of a solution containing water at 50 ° C. was performed by evaporation to obtain a carbon content of 19.7 mol%, a weight average molecular weight of 3200, Si-CH SiZSi—O—Si (molar ratio) of 0.487.
- a film-forming composition C containing a hydrolyzed condensate was obtained.
- This composition C had a sodium content of 0.7 ppb, a potassium content of 0.5 ppb, and an iron content of 0.8 ppb.
- composition D was obtained.
- Composition D was 23.5 mol%, with a sodium content of 0.8 ppb, a calicum content of SO. 5 ppb, and an iron content of SO. 9 ppb.
- composition E (Molar ratio) A film-forming composition E containing 0.000 polysiloxane was obtained.
- Composition E had a sodium content of 0.6 ppb, a potassium content of 0.7 ppb, and an iron content of 0.9 ppb.
- reaction solution was cooled to room temperature.
- 250 g of a solution containing water was removed by evaporation, and the carbon content was 16.7 mol%, the weight average molecular weight was 4,400, and the Si-CH SiZSi—O—Si (molar ratio) was 0.132.
- composition F containing a hydrolyzed condensate was obtained.
- Composition F has a carbon content of 16.7 mol%, a sodium content of 0.8 ppb, a potassium content of 0.5 ppb, and an iron content of 0.9 ppb.
- compositions obtained in Synthesis Example 16 were applied on a silicon wafer by a spin coating method, and then placed on a hot plate at 90 ° C for 3 minutes, and then under a nitrogen atmosphere at 200 ° C for 3 minutes.
- the substrate was dried and baked under the curing conditions shown in Table 1.
- the polymer film obtained after the firing (hereinafter referred to as “silica-based film”) was evaluated according to the above-mentioned evaluation method. Table 1 shows the evaluation results.
- the coating film was cured by irradiating a predetermined amount of electron beam within the heating time under the heating conditions shown in Table 1, whereas in Comparative Example 15, the heat treatment was performed. Only the coating was cured.
- IR spectra of the silica-based films obtained in Example 2 and Comparative Example 2 were measured, and the results are shown in FIG. In FIG. 1, it can be seen that peaks appearing only after EB irradiation are present at the positions indicated by A and B.
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Abstract
Description
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EP05739243A EP1746123A4 (en) | 2004-05-11 | 2005-05-11 | PROCESS FOR FORMING ORGANIC SILICA FILM, ORGANIC SILICA FILM, WIRING STRUCTURE, SEMICONDUCTOR DEVICE, AND COMPOSITION FOR FILM FORMATION |
PCT/JP2005/008608 WO2005108469A1 (ja) | 2004-05-11 | 2005-05-11 | 有機シリカ系膜の形成方法、有機シリカ系膜、配線構造体、半導体装置、および膜形成用組成物 |
KR1020067025874A KR101140535B1 (ko) | 2004-05-11 | 2005-05-11 | 유기 실리카계 막의 형성 방법, 유기 실리카계 막, 배선구조체, 반도체 장치 및 막 형성용 조성물 |
US11/596,188 US20080038527A1 (en) | 2004-05-11 | 2005-05-11 | Method for Forming Organic Silica Film, Organic Silica Film, Wiring Structure, Semiconductor Device, and Composition for Film Formation |
JP2006513040A JPWO2005108469A1 (ja) | 2004-05-11 | 2005-05-11 | 有機シリカ系膜の形成方法、有機シリカ系膜、配線構造体、半導体装置、および膜形成用組成物 |
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US8656039B2 (en) * | 2003-12-10 | 2014-02-18 | Mcafee, Inc. | Rule parser |
EP1705206A4 (en) * | 2004-01-16 | 2009-06-24 | Jsr Corp | PROCESS FOR PREPARING POLYMER, POLYMER, COMPOSITION FOR FORMING AN INSULATING FILM, PROCESS FOR PREPARING INSULATING FILM AND INSULATING FILM |
WO2005082976A1 (ja) | 2004-02-26 | 2005-09-09 | Jsr Corporation | ポリマーおよびその製造方法、絶縁膜形成用組成物、ならびに絶縁膜およびその形成方法 |
JP5110238B2 (ja) * | 2004-05-11 | 2012-12-26 | Jsr株式会社 | 絶縁膜形成用組成物およびその製造方法、ならびにシリカ系絶縁膜およびその形成方法 |
JP5110239B2 (ja) * | 2004-05-11 | 2012-12-26 | Jsr株式会社 | 有機シリカ系膜の形成方法、膜形成用組成物 |
WO2005108469A1 (ja) * | 2004-05-11 | 2005-11-17 | Jsr Corporation | 有機シリカ系膜の形成方法、有機シリカ系膜、配線構造体、半導体装置、および膜形成用組成物 |
JP2007045966A (ja) * | 2005-08-11 | 2007-02-22 | Fujifilm Corp | 絶縁膜形成用組成物、絶縁膜、およびその製造方法 |
JP2007070480A (ja) * | 2005-09-07 | 2007-03-22 | Fujifilm Corp | 膜形成用組成物、絶縁膜およびその製造方法 |
JP5120547B2 (ja) * | 2006-02-02 | 2013-01-16 | Jsr株式会社 | 有機シリカ系膜およびその形成方法、半導体装置の絶縁膜形成用組成物およびその製造方法、ならびに配線構造体および半導体装置 |
US20100140754A1 (en) * | 2006-08-15 | 2010-06-10 | Jsr Corporation | Film-forming material, silicon-containing insulating film and method for forming the same |
JPWO2008066060A1 (ja) * | 2006-11-30 | 2010-03-04 | Jsr株式会社 | ポリマーの製造方法、絶縁膜形成用組成物、ならびにシリカ系絶縁膜およびその製造方法 |
JP5170445B2 (ja) * | 2007-02-14 | 2013-03-27 | Jsr株式会社 | ケイ素含有膜形成用材料、ならびにケイ素含有絶縁膜およびその形成方法 |
WO2009008041A1 (ja) * | 2007-07-06 | 2009-01-15 | Fujitsu Limited | 絶縁膜材料、多層配線基板及びその製造方法、並びに、半導体装置及びその製造方法 |
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- 2005-01-14 KR KR1020067016326A patent/KR101185644B1/ko not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
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US7875317B2 (en) | 2011-01-25 |
EP1705208A1 (en) | 2006-09-27 |
EP1705208B1 (en) | 2013-03-20 |
WO2005068540A1 (ja) | 2005-07-28 |
JPWO2005068540A1 (ja) | 2007-12-27 |
EP1705208A4 (en) | 2012-03-28 |
KR101185644B1 (ko) | 2012-09-24 |
US20070020467A1 (en) | 2007-01-25 |
JP5105041B2 (ja) | 2012-12-19 |
TW200538491A (en) | 2005-12-01 |
KR20060123547A (ko) | 2006-12-01 |
TWI316524B (ja) | 2009-11-01 |
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