CN1463279A - 有机硅酸酯聚合物和从其得到的绝缘膜 - Google Patents
有机硅酸酯聚合物和从其得到的绝缘膜 Download PDFInfo
- Publication number
- CN1463279A CN1463279A CN02801827A CN02801827A CN1463279A CN 1463279 A CN1463279 A CN 1463279A CN 02801827 A CN02801827 A CN 02801827A CN 02801827 A CN02801827 A CN 02801827A CN 1463279 A CN1463279 A CN 1463279A
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- Prior art keywords
- organic
- polymer
- preparation
- silane compound
- insulating film
- Prior art date
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- Granted
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- 229920000642 polymer Polymers 0.000 claims abstract description 86
- 239000000126 substance Substances 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 37
- 230000007062 hydrolysis Effects 0.000 claims abstract description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- -1 silicic acid ester Chemical class 0.000 claims description 108
- 229910000077 silane Inorganic materials 0.000 claims description 78
- 238000002360 preparation method Methods 0.000 claims description 53
- 235000012239 silicon dioxide Nutrition 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 34
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 20
- 238000009833 condensation Methods 0.000 claims description 16
- 230000005494 condensation Effects 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229920000620 organic polymer Polymers 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 238000003747 Grignard reaction Methods 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 229910052802 copper Chemical group 0.000 claims description 5
- 239000010949 copper Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 229910000765 intermetallic Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 4
- 239000000084 colloidal system Substances 0.000 claims description 4
- 230000014509 gene expression Effects 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical group [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 abstract description 7
- 239000007859 condensation product Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000003989 dielectric material Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000011229 interlayer Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000034189 Sclerosis Diseases 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical compound CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 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
- 239000004020 conductor Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000001282 organosilanes Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
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- 159000000003 magnesium salts Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
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- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- AWBIJARKDOFDAN-UHFFFAOYSA-N 2,5-dimethyl-1,4-dioxane Chemical compound CC1COC(C)CO1 AWBIJARKDOFDAN-UHFFFAOYSA-N 0.000 description 1
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- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
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- 239000005046 Chlorosilane Substances 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
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- 239000008199 coating composition Substances 0.000 description 1
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- 239000000470 constituent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
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- 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
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- 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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Abstract
本发明涉及具有高性能和高密度的次产生电器件如半导体器件必须的低介电物质,特别地涉及低介电有机硅酸酯聚合物、碳桥接低聚物的水解缩合产物的制备方法,以及使用由该方法制备的有机硅酸酯聚合物制造绝缘膜的方法,本发明涉及包括由该方法制备的绝缘膜的电器件。根据本发明方法制备的有机硅酸酯聚合物是热稳定的,且具有良好的成膜性能、优异的机械强度和耐裂缝性,从其制造的膜具有优异的绝缘性能、膜均匀性、介电性能、耐裂缝性、和机械强度。
Description
技术领域
本发明涉及具有高性能和高密度,次产生电器件如半导体器件所必须的低介电材料。更具体地,本发明涉及有机硅酸酯聚合物的制备方法,有机硅酸酯聚合物为热稳定的且具有良好的成膜性能和优异的机械强度及耐裂缝性,本发明并且涉及使用由该方法制备的有机硅酸酯聚合物制造绝缘膜的方法。
背景技术
半导体工业在集成电路器件,如存储器和逻辑芯片中,正朝向增加器件复杂性、要求收缩几何尺寸和具有更大尺寸密度的更高的组件集成而发展。这导致布线水平数目的增加和布线间距的降低以增加布线密度。目前的前沿逻辑处理器具有高密度互连的7-8水平,并且互连线宽度预定在约2004年降低到0.1μm。
当器件尺寸收缩到小于0.25μm时,由于电阻电容耦合的传播延迟、串音噪声、和功率耗散变得显著。更小的线尺寸增加金属导线的电阻率,并且窄的金属间空隙增加金属导线之间的电容。因此,尽管当特征尺寸降低时器件的开关速度会增加,但是互连延迟成为总延迟的主要部分并限制总体芯片性能。因此,为制备具有高速度的芯片,应当使用具有低电阻的导体和具有低介电常数的介电材料。此外,低介电材料的使用可显著地降低功率耗散和串音噪声。
最近,几个半导体器件制造商已经使用具有高电导率的铜布线代替常规的铝布线,将显示出性能改进为20%或更大的测试产品投入市场。最近已经在进行用于互连的,显示低介电常数性能的新材料使用的转换。如果在集成电路的互连层之间的介电膜可使用这些材料,则对操作速度的影响会与由从铝到铜技术的转换导致的影响相同。例如,如果介电材料的介电常数从4.0变化到约2.5,IC操作速度会改进约20%。
用于半导体集成电路器件的间层介电材料主要是SiO2,它一般使用化学气相沉积(CVD)形成以承受与形成电介质的条件下相关的各种加工操作。硅热氧化膜,它具有最低的介电常数,其介电常数约为4.0。已经尝试通过向由CVD沉积的无机膜中引入氟原子以降低介电常数。然而,大量氟原子的引入降低化学和热稳定性,使得在真实实施中达到的介电常数约为3.5。氟化氧化物可提供直接的短期解决方案,可能要求向具有3以下介电常数的新类型绝缘材料的转换。
一类候选材料是有机聚合物,其中一些的介电常数小于3.0。已知向这样有机聚合物中引入氟进一步降低介电常数。然而,大多数有机聚合物并不具有芯片级半导体绝缘体要求的物理化学性能,特别是热稳定性和机械性能(足以承受400~450℃范围内的后端线制造温度)。很少的有机聚合物在大于450℃的温度下稳定。它们也具有低玻璃化转变温度并且因此它们的弹性在高温下显著降低,并且它们具有非常高的线性膨胀系数。由于在半导体IC集成和组装工艺期间温度上升到450℃,因此获得的低热稳定性和弹性以及高线性膨胀系数可劣化器件的可靠性。
最近,为解决有机聚合物的热稳定性问题,已经出现使用溶胶工艺的有机硅酸酯聚合物的开发。特别地,已经建议介电常数在约2.7~3.3范围内的有机SOG(旋涂玻璃)用作间层电介质,其中有机组分的侧链(烷基如甲基)键合到硅氧烷键的后键链上。然而,有机硅酸酯聚合物显示出差的机械性能。例如,在工艺期间除非膜非常薄(通常<1μm),聚甲基硅倍半氧烷显示裂缝形成,并且显示由于烷基引入的低机械模量。
Miller等人已经报导了通过引入少量聚合物取代基如聚酰亚胺来增韧硅倍半氧烷材料体系的方法。混合无机细微粒粉末的方法已知为改进有机硅酸酯机械强度的方法。尽管已经提出各种体系,但是需要具有合适低介电常数和适当物理化学性能,用作下一代IC器件间层电介质的材料。
发明内容
因此,考虑到现有技术的问题进行本发明,本发明的目的是提供用于非常低介电间层布线绝缘膜的低介电材料的制备方法,该绝缘膜可使半导体器件速度较高,降低功率消耗,并显著地降低金属布线之间的串音。
本发明的另一个目的是提供具有优异耐裂缝性、机械强度、成膜性能、和介电性能的有机硅酸酯聚合物的制备方法,并提供包含根据该方法制备的聚合物的绝缘膜的制造方法。
为达到这些目的,本发明提供制备有机硅酸酯聚合物的两种方法。
第一种方法包括:
a)提供由如下化学通式1表示的有机金属硅烷化合物;
b)引起单独的由化学通式1表示的a)有机金属硅烷化合物的格氏反应,以制备碳桥接的硅烷低聚物以及除去金属化合物副产物;
c)在有机溶剂中,混合b)碳桥接的硅烷低聚物,并向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物;
化学通式1:
R1 pR2 3-pSiR3MX
其中
R1独立地是氢、氟、芳基、乙烯基、烯丙基、或氟取代的或未取代的线性或支化C1-4烷基;
R2独立地是氯、乙酰氧基、羟基、或线性或支化C1-4烷氧基;
R3是C1-6烃;
M是镁、汞、或铜;
X是卤素;
p是0-2的整数。
此外,第二种方法包括:
a)提供由以上化学通式1表示的有机金属硅烷化合物;
b)引起如下物质的格氏反应:
i)由化学通式表示的a)有机金属硅烷化合物;和
ii)硅烷化合物或硅烷低聚物
以制备碳桥接的硅烷低聚物和除去金属化合物副产物;
c)在有机溶剂中,混合b)碳桥接的硅烷低聚物,向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物。
本发明也提供用于形成半导体器件绝缘膜的组合物,该绝缘膜包括由以上方法之一制备的有机硅酸酯聚合物,本发明并且提供包括涂敷和固化组合物的制造半导体器件绝缘膜的方法。
具体地,本发明用于形成半导体器件绝缘膜的组合物包括:
a)由每种有机硅酸酯聚合物制备方法制备的有机硅酸酯聚合物;
b)有机溶剂。
形成绝缘膜的组合物可进一步包括:
c)一种或多种选自如下的添加剂:有机分子、有机聚合物、有机树枝状聚合物、胶体二氧化硅、气溶胶、干溶胶、和表面活性剂。
本发明也提供半导体器件绝缘膜的制造方法,包括:
a)提供由每种有机硅酸酯聚合物制备方法制备的有机硅酸酯聚合物;
b)在溶剂中溶解有机硅酸酯聚合物,和在需要时在溶剂中溶解添加剂;
c)在半导体器件衬底上涂敷有机硅酸酯聚合物溶液;
d)干燥和固化涂敷的绝缘膜,
本发明也提供包括由该方法制备的绝缘膜的半导体器件。
具体实施方式
现在更详细地描述本发明。
根据本发明,从由如下化学通式1表示的有机金属硅烷化合物制备桥接的有机硅烷低聚物,从该低聚物制备有机硅酸酯聚合物。本发明提供用于形成绝缘膜的组合物,该绝缘膜包括有机硅酸酯聚合物,本发明提供包括有机硅酸酯聚合物的半导体器件绝缘膜的制造方法,和包括绝缘膜的半导体器件。
根据本发明制备的有机硅酸酯聚合物,如果被涂敷到半导体器件的绝缘膜上,具有优异的绝缘性能、膜均匀性、介电性能、耐裂缝性、和机械强度。
如下反应式是本发明有机硅酸酯聚合物制备方法的例子。
第一制备方法伴随如下反应式1。
反应式1:
如所示的,单独的化学通式1有机金属硅烷化合物的格氏反应制备碳桥接的硅烷低聚物,其中除去金属化合物副产物。将碳桥接的硅烷低聚物溶于有机溶剂,向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物。同样,在有机溶剂中混合碳桥接的硅烷低聚物和硅烷化合物或硅烷低聚物,向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物。
第二制备方法伴随如下反应式2。
化学通式1有机金属硅烷化合物和硅烷化合物或硅烷低聚物间的格氏反应制备碳桥接的硅烷低聚物。将碳桥接的硅烷低聚物溶于有机溶剂,向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物。同样然后在有机溶剂中混合碳桥接的硅烷低聚物和硅烷化合物或硅烷低聚物,向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物。
用于制备本发明有机硅酸酯聚合物的原材料是满足化学通式1的有机金属硅烷化合物。有机金属硅烷化合物优选通过如下方式制备:
a)向反应容器中引入金属和干燥它;
b)向容器中加入有机溶剂和由如下化学通式2表示的硅烷化合物以反应它们以制备满足以上化学通式1的有机金属硅烷化合物。
化学通式2:
R1 pR2 3-pSiR3X
(其中
R1独立地是氢、氟、芳基、乙烯基、烯丙基、或氟取代的或未取代的线性或支化C1-4烷基;
R2独立地是氯、乙酰氧基、羟基、或线性或支化C1-4烷氧基;
R3是C1-6烃;
X是卤素;和
p是0-2的整数。
即,将氯烷基硅烷,满足以上化学通式2的有机硅烷化合物与金属Mg反应以制备一种满足化学通式1的有机金属硅烷化合物。
用于制备碳桥接硅烷低聚物或最终产物有机硅酸酯聚合物的所述方法中的硅烷化合物包括:包括硅、碳、氧、和氢的有机硅烷单体,以及可以从其制备的有机硅烷低聚物。优选,由如下化学通式3表示的硅烷化合物或其低聚物可用于制备碳桥接硅烷低聚物或最终产物有机硅酸酯聚合物。
化学通式3:
R4 qR5 4-qSi
(其中
R4独立地是氢、氟、芳基、乙烯基、烯丙基、或氟取代的或未取代的线性或支化C1-4烷基;
R5独立地是氯、乙酰氧基、羟基、或线性或支化C1-4烷氧基;
q是0-3的整数)。
根据本发明,在溶剂存在下将碳桥接的硅烷低聚物和硅烷化合物或硅烷低聚物水解和缩合,同时加入水和催化剂以获得具有具体分子量的有机硅酸酯聚合物,因此用于形成绝缘膜的组合物。
用于水解和缩合或用于膜涂料的溶剂包括会溶解组合物以形成硅烷化合物或硅烷低聚物和碳桥接硅烷低聚物的均匀液体混合物的任何试剂或试剂混合物。用于本发明的溶剂包括,作为例子,脂族烃如正戊烷、异戊烷、正己烷、异己烷、2,2,4-三甲基戊烷、环己烷、甲基环己烷等;芳族烃如苯、甲苯、二甲苯、三甲苯、乙苯、甲基乙苯等;醇如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、环己醇、甲基环己醇、甘油等;醚如四氢呋喃、2-甲基四氢呋喃、乙醚、正丙醚、异丙醚、二甘醇二甲醚、二噁烷、二甲基二噁烷、乙二醇单甲醚、乙二醇二甲醚、乙二醇二乙醚、丙二醇单甲醚、丙二醇二甲醚等;酯如碳酸二乙酯、乙酸甲酯、乙酸乙酯、乳酸乙酯、乙二醇单甲醚乙酸酯、丙二醇单甲醚乙酸酯、乙二醇二乙酸酯等;和酰胺如N-甲基吡咯烷酮、甲酰胺、N-甲基甲酰胺、N-乙基甲酰胺、N,N-二甲基乙酰胺、N,N-二乙基乙酰胺等。
在反应之后除去用于水解和缩合的所有溶剂以获得有机硅酸酯聚合物油或粉末,有机硅酸酯聚合物可溶于用于形成膜的有机溶剂中,或者用于水解和缩合的有机溶剂可直接用于形成膜。可以一起使用两种或多种有机溶剂。
本发明使用催化剂以促进水解和缩合。用于水解和缩合的催化剂包括酸催化剂、碱催化剂、金属螯合物化合物、盐催化剂等。例如,酸催化剂包括盐酸、硝酸、硫酸、磷酸、甲酸、苯磺酸、甲苯磺酸、乙酸、草酸、丙二酸、马来酸、富马酸、柠檬酸、丙酸等;碱催化剂包括氨、氢氧化钠、氢氧化钙、氢氧化钾、三甲胺、三乙胺、二乙醇胺、三乙醇胺、二甲基乙醇胺、单甲基二乙醇胺二氮杂双环十一碳烯、吡啶、吡咯哌啶、胆碱、吡咯烷、哌嗪等。金属螯合物化合物包括含有金属如铝、钛、锆、锡、钽的有机金属化合物等;盐催化剂包括共轭酸,和共轭碱化合物如乙酸铵。酸,碱,金属螯合物化合物,和盐催化剂可以单独使用或以结合使用,并且可以分阶段使用它们的两种或多种。
加入的催化剂数量可以是促进桥接硅烷低聚物和硅烷化合物或硅烷低聚物的水解和缩合反应的任何数量,并且最优数量会依赖于催化剂的化学组成以及水解和缩合进行时的温度。一般情况下,每1摩尔硅烷化合物中的硅原子,催化剂的加入量为0.00001-1摩尔,优选0.5摩尔或更小。如果催化剂的加入量超过1摩尔每1摩尔硅烷化合物中的硅原子,则反应速率会非常高并且会难以控制分子量和可能容易地产生凝胶。
在本发明中,加入水以引起硅烷化合物的水解。水的数量合适地为0.1-20摩尔,优选1-10摩尔每1摩尔硅烷化合物中的硅原子,并且它可以分阶段加入或连续加入。催化剂可以预先加入到有机溶剂中,或当加入水时它可以溶解或分散。
当要使产物具有所需的分子量时,对反应温度没有特别的限制。温度可优选不高于使用的有机溶剂的沸点,并且可以优选为0℃-100℃以控制获得的水解产物的分子量。在水解和缩合时间下对反应时间没有特别的限制,反应可以在产物达到所述分子量的时间下完成。通常优选设定最终产物的分子量为重均分子量的500-1,000,000以形成均匀的涂料膜。
通过采用有机溶剂溶解由以上方法制备的有机硅酸酯聚合物制备本发明用于形成绝缘膜的涂料组合物。如所需,各种添加剂,如有机分子、有机聚合物、有机树枝状聚合物、胶体二氧化硅、气溶胶、干溶胶、和表面活性剂等可以根据它的目的加入到用于形成确定数量绝缘膜的组合物中。
在固体内容物溶解的范围内,可以合适地从溶液所需粘度或涂料膜厚度的角度来选择溶液中固体内容物浓度。一般情况下本发明组合物的固体浓度为2-60wt%,优选5-40wt%。
通过在衬底如硅晶片、SiO2晶片、SiN晶片、半导体化合物等上涂敷绝缘膜组合物形成本发明的绝缘膜。可以通过标准方法如旋转涂敷、流动涂敷、浸涂、和喷淋涂敷形成绝缘膜。当将本发明的组合物涂敷到半导体器件的间层介电膜上时,优选是旋转涂敷方法,这是由于膜厚度的平面内分布会因此是均匀的。
可以通过改变组合物的粘度和旋转涂敷器的旋转速度控制膜的厚度,对于半导体器件多层电路的间层绝缘膜,0.2-2μm是合适的。
可以通过在涂敷工艺之后的干燥和固化(硬化)工艺形成具有三维结构的有机硅酸酯聚合物绝缘膜。通常地,分别在30-250℃和300-600℃下进行干燥和固化,特别地优选在350-500℃下进行固化。如果固化温度超过600℃,有机硅酸酯聚合物的热稳定性会降低,如果它小于300℃,由于有机硅酸酯聚合物的缩聚并不完全发生,膜的强度会降低,并且由于残余官能团的存在,介电性能会降低。
干燥和固化工艺可以连续进行同时以具体速率升高温度,或它们可以分阶段进行。如果分阶段进行,干燥和固化工艺合适地分别进行1分钟和5小时。可以使用热板、烘箱、加热炉等,在惰性气体环境如氮气或氩气、氦气环境,如采用含氧气体(例如,空气)的氧气环境下,真空或在氨和含氢气体环境下,进行加热。干燥和固化可以由相同的加热方法或由不同的加热方法进行。
在固化工艺之后,如需要,可以通过通常的方法进行表面处理以最小化绝缘膜中的羟基数量。通过如下方式进行表面处理以除去残余羟基:在硅烷化合物溶液如六甲基二硅氮烷、烷基氯硅烷、和烷基乙酰氧基硅烷中浸渍绝缘膜,以引起其间的反应和干燥它,或通过在还原气体环境如氢气或含氟气体气氛下,在300-600℃下加热绝缘膜1分钟或更长。
由于它具有优异的绝缘性能、膜均匀性、介电性能、耐裂缝性、和机械强度,由该方法获得的膜合适地用于LSI、系统LSI、DRAM、SDRAM、D-RDRAM等的半导体器件的间层绝缘膜;保护膜如用于半导体器件的表面涂料膜;用于多层布线衬底的间层绝缘膜;和用于液体显示设备的保护膜或绝缘保护膜。
现在参考如下实施例和对比例更详细地解释本发明。然而,这些实施例用于说明本发明,但本发明并不限于这些实施例。
实施例:
实施例1:
(由化学通式1表示的有机金属硅烷化合物的制备)
在反应器中引入0.71g镁并干燥它之后,向其中加入15ml溶剂蒸馏的四氢呋喃(THF)。将混合物的温度降低到0℃,将5g氯甲基三乙氧基硅烷、满足化学通式2的有机硅烷化合物,缓慢加入以反应直到制备格氏试剂和反应由NMR确认。
(碳桥接低聚物的制备)
在初始反应完成之后,反应持续12小时以形成碳桥接的低聚物。然后向其中加入50ml己烷以沉淀镁盐并将沉淀物采用才利特过滤,然后在真空烘箱中完全除去有机溶剂以获得产物。
(有机硅酸酯聚合物的制备)
在11.3ml四氢呋喃溶剂中混合1.5g获得的产物和4.64g甲基三甲氧基硅烷,和满足化学通式3的有机硅烷化合物。
将混合物的温度降低到0℃,将1.78ml蒸馏水和0.21ml催化剂、2N盐酸缓慢加入到其中以反应30分钟。然后,将温度缓慢升高到80℃和将反应持续16小时同时加热回流。在反应之后,将混合物采用二乙醚溶剂稀释并采用蒸馏水洗涤3-4次直到酸性变成中性。在真空烘箱中从获得的有机层完全除去剩余的溶剂以获得固体(粉末)产物。
(绝缘膜的制备)
将300mg获得的粉末溶于甲基异丁基酮以设定溶液总重量为1.5g。通过过滤器从获得的溶液除去杂质并旋转涂敷溶液以获得薄膜。通过干燥和固化工艺,在2℃每分钟的速率下升高温度到430℃并在氮气环境下保持温度1小时而制备绝缘膜。
实施例2:
(由化学通式1表示的有机金属硅烷化合物的制备)
在反应器中引入0.71g镁和干燥它之后,向其中加入15ml溶剂蒸馏的四氢呋喃(THF)。将混合物的温度降低到0℃,将0.2g二氯甲烷和0.2g氯甲基三乙氧基硅烷、满足化学通式2的有机硅烷化合物,缓慢加入到其中。当要开始产生格氏试剂时,将4.8g氯甲基三乙氧基硅烷、满足化学通式2的有机化合物,进一步缓慢加入以制备格氏试剂,反应由NMR确认。
(碳桥接低聚物的制备)
将5.37g四甲氧基硅烷、满足化学通式3的化合物、和15ml四氢呋喃缓慢加入到以上溶液中并将混合物在0℃下搅拌2小时。向其中加入50ml己烷以沉淀镁盐,将沉淀物采用才利特过滤。然后在真空烘箱中从中完全除去有机溶剂以获得碳桥接的硅烷低聚物产品。
(有机硅酸酯聚合物的制备)
在30ml四氢呋喃溶剂中混合44.2g获得的碳桥接硅烷低聚物和18.17g甲基三甲氧基硅烷、满足化学通式3的有机硅烷化合物。
将混合物的温度降低到0℃,将8.0ml蒸馏水和0.98ml催化剂、5N盐酸缓慢加入到其中以反应30分钟。然后,将温度缓慢升高到80℃并将反应持续16小时同时加热回流。在反应之后,将混合物采用二乙醚溶剂蒸馏并采用蒸馏水洗涤3-4次直到酸性变成中性。在真空烘箱中从获得的有机层完全除去剩余的溶剂以获得固体(粉末)产物。
(绝缘膜的制备)
通过如实施例1中相同的方法干燥和固化获得的粉末,制备绝缘膜。
实施例3:
(有机硅酸酯聚合物的制备)
在60ml四氢呋喃溶剂中混合9g由实施例1中相同方法获得的碳桥接硅烷低聚物、30.0g甲基三甲氧基硅烷、和3.4g四甲氧基硅烷。
将混合物的温度降低到0℃,将37ml催化剂、0.01N硝酸缓慢加入到其中以反应30分钟。然后,将温度缓慢升高到70℃并将反应持续16小时同时加热回流。在反应之后,将混合物采用二乙醚溶剂稀释和采用蒸馏水洗涤3-4次直到酸性变成中性。在真空烘箱中从获得的有机层完全除去剩余的溶剂以获得固体内容物。
(绝缘膜的制备)
通过如实施例1中相同的方法干燥和固化获得的粉末,制备绝缘膜。
对比例1:
将7.26g甲基三甲氧基硅烷、有机硅烷化合物、和4.05ml蒸馏水在10ml四氢呋喃(THF)溶剂中混合,并在氮气环境下向其中缓慢加入0.80ml的2N盐酸。
在室温下反应它们30分钟之后,缓慢增加温度并将反应持续24小时同时加热回流。
在反应之后,将溶液的温度降低到室温,并将溶液采用二乙醚溶剂稀释和采用水洗涤3-4次直到酸性变成中性。将硫酸镁引入到获得的有机层中以从中完全除去剩余的水。在真空烘箱中从获得的有机层完全除去溶剂以获得固体(粉末)产物。
(绝缘膜的制备)
通过如实施例1中相同的方法干燥和硬化获得的粉末,制备绝缘膜。
通过如下方法a)-c)测量在实施例1,2,3和对比例1中制备的有机硅酸酯聚合物的物理性能,以获得示于表1的结果。
a)分子量(质量平均分子量:Mw)-由凝胶渗透色谱(GPC)使用聚苯乙烯作为标准物获得的相对分子量数值。
b)薄膜的机械性能-在2X2英寸Si晶片上旋转涂敷和在430℃下在N2环境下硬化1小时之后测量。
i)硬度-使用Hysitron Inc的Tribolndenter测量。
ii)耐裂缝性-制备1μm薄膜以观察是否发生裂缝。
c)膜的介电性能-在Si晶片上制造MIM(金属/绝缘体/半导体)器件和在1MHz下使用HP Company的LCR表测量介电性能。
结果见表1。
实施例1 | 实施例2 | 实施例3 | 对比例1 | |
Mw | 11807 | 27716 | 3100 | 11000 |
硬度 | 0.62 | 0.58 | 1.1 | 0.32 |
耐裂缝性 | 2.4E12 | 5.3E-12 | 1.2E-12 | 1.3E-9 |
介电常数 | 2.78 | 2.75 | 2.83 | 2.73 |
表1
如表1所示,从本发明有机硅酸酯聚合物制造的薄膜有良好的介电性能和改进的机械强度以及耐裂缝性。
根据本发明制备的有机硅酸酯聚合物是热稳定的且具有良好的成膜性能,优异的机械强度和耐裂缝性,从其制造的膜具有优异的绝缘性能、膜均匀性、介电性能、耐裂缝性、和机械强度。
Claims (9)
1.一种有机硅酸酯聚合物的制备方法,包括如下步骤:
a)提供由如下化学通式1表示的有机金属硅烷化合物;
b)引起如下物质的格氏反应:
i)单独的a)有机金属硅烷化合物,或
ii)a)有机金属硅烷化合物和硅烷化合物或硅烷低聚物,
以制备碳桥接的硅烷低聚物并除去金属化合物副产物;
c)在有机溶剂中,混合b)碳桥接的硅烷低聚物,向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物;
化学通式1:
R1 PR2 3-pSiR3MX
(其中
R1独立地是氢、氟、芳基、乙烯基、烯丙基、或氟取代的或未取代的线性或支化C1-4烷基;
R2独立地是氯、乙酰氧基、羟基、或线性或支化C1-4烷氧基;
R3是C1-6烃;
M是镁、汞、或铜;
X是卤素;
p是0-2的整数)。
2.根据权利要求1的有机硅酸酯聚合物的制备方法,其中通过如下方式制备a)有机金属硅烷化合物:
i)向反应容器中引入金属和干燥它;
ii)向反应容器中加入有机溶剂和由如下化学通式2表示的硅烷化合物并反应它们:
化学通式2:
R1 PR2 3-pSiR3X
(其中
R1独立地是氢、氟、芳基、乙烯基、烯丙基、或氟取代的或未取代的线性或支化C1-4烷基;
R2独立地是氯、乙酰氧基、羟基、或线性或支化C1-4烷氧基;
R3是C1-6烃;
X是卤素;
p是0-2的整数)。
3.根据权利要求1的有机硅酸酯聚合物的制备方法,其中b)ii)和c)ii)的硅烷化合物或硅烷低聚物是由如下化学通式3表示的硅烷化合物或其低聚物:
化学通式3:
R4 qR5 4-qSi
(其中
R4独立地是氢、氟、芳基、乙烯基、烯丙基、或氟取代的或未取代的线性或支化C1-4烷基;
R5独立地是氯、乙酰氧基、羟基、或线性或支化C1-4烷氧基;
q是0-3的整数)。
4.根据权利要求1的方法制备的有机硅酸酯聚合物。
5.一种用于形成半导体器件的绝缘膜的组合物,包括:
a)由包括如下步骤的方法制备的有机硅酸酯聚合物:
i)提供由如下化学通式1表示的有机金属硅烷化合物;
ii)引起如下物质的格氏反应:
单独的i)有机金属硅烷化合物,或
i)有机金属硅烷化合物和硅烷化合物或硅烷低聚物,
以制备碳桥接的硅烷低聚物并除去金属化合物副产物;
iii)在有机溶剂中,混合ii)碳桥接的硅烷低聚物,向其中加入水和催化剂以引起水解和缩合以制备有机硅酸酯聚合物;
b)有机溶剂;
化学通式1:
R1 PR2 3-pSiR3MX
(其中
R1独立地是氢、氟、芳基、乙烯基、烯丙基、或氟取代的或未取代的线性或支化C1-4烷基;
R2独立地是氯、乙酰氧基、羟基、或线性或支化C1-4烷氧基;
R3是C1-6烃;
M是镁、汞、或铜;
X是卤素;
p是0-2的整数)。
6.根据权利要求5的用于形成绝缘膜的组合物,进一步包括:
c)一种或多种选自如下的添加剂:有机分子、有机聚合物、有机树枝状聚合物、胶体二氧化硅、气溶胶、干溶胶、和表面活性剂。
7.一种制造半导体器件绝缘膜的方法,包括如下步骤:
a)在半导体器件的衬底上涂敷权利要求5的组合物;
b)干燥和固化涂敷的绝缘膜。
8.根据权利要求7的制造绝缘膜的方法,其中a)组合物进一步包括一种或多种选自如下的添加剂:有机分子、有机聚合物、有机树枝状聚合物、胶体二氧化硅、气溶胶、干溶胶、和表面活性剂。
9.一种半导体器件,包括根据权利要求7的方法制备的绝缘膜。
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EP (1) | EP1392761A1 (zh) |
JP (1) | JP3819391B2 (zh) |
KR (1) | KR100451044B1 (zh) |
CN (1) | CN100422240C (zh) |
WO (1) | WO2002098955A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101517001B (zh) * | 2006-09-18 | 2011-11-09 | Lg化学株式会社 | 用于制备保护膜的低温快速固化组合物、由该组合物制备的保护膜和包括该保护膜的基板 |
CN101292343B (zh) * | 2005-09-01 | 2012-10-31 | 飞思卡尔半导体公司 | 在双镶嵌互连上的覆盖层的形成 |
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KR100451044B1 (ko) * | 2001-06-07 | 2004-10-02 | 주식회사 엘지화학 | 유기실리케이트 중합체의 제조방법, 및 이를 이용한절연막의 제조방법 |
KR100422916B1 (ko) * | 2001-06-26 | 2004-03-12 | 주식회사 엘지화학 | 유기실리케이트 중합체 및 이를 함유하는 저유전 절연막 |
KR100508903B1 (ko) * | 2002-05-06 | 2005-08-17 | 주식회사 엘지화학 | 저유전 절연막 형성용 조성물 및 절연막 제조 방법 |
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 |
WO2005068540A1 (ja) * | 2004-01-16 | 2005-07-28 | Jsr Corporation | 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 |
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 |
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 |
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 |
KR101872684B1 (ko) * | 2014-04-08 | 2018-06-29 | (주)필스톤 | 고방열 및 고내전압 절연코팅제 조성물 및 그의 제조방법 |
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GB591149A (en) * | 1944-11-30 | 1947-08-08 | John Edward Hackford | Improvements in or relating to the production of organo-silicon compounds by the grignard reaction |
KR940007414B1 (ko) * | 1991-06-14 | 1994-08-18 | 한국과학기술연구원 | 1,3-디실라시클로부탄 유도체 및 그 제조방법 |
US5912313A (en) * | 1995-11-22 | 1999-06-15 | The B. F. Goodrich Company | Addition polymers of polycycloolefins containing silyl functional groups |
JPH1116904A (ja) * | 1997-06-26 | 1999-01-22 | Mitsubishi Electric Corp | 半導体装置及びその製造方法 |
US6140445A (en) * | 1998-04-17 | 2000-10-31 | Crompton Corporation | Silane functional oligomer |
US6562465B1 (en) * | 1998-04-24 | 2003-05-13 | Catalysts & Chemicals Industries Co., Ltd. | Coating liquid for forming a silica-containing film with a low-dielectric constant and substrate coated with such a film |
US6147009A (en) * | 1998-06-29 | 2000-11-14 | International Business Machines Corporation | Hydrogenated oxidized silicon carbon material |
JP4305587B2 (ja) | 1999-04-27 | 2009-07-29 | Jsr株式会社 | 半導体装置用の層間絶縁膜形成用材料 |
US6107357A (en) * | 1999-11-16 | 2000-08-22 | International Business Machines Corporatrion | Dielectric compositions and method for their manufacture |
KR100425242B1 (ko) * | 2000-05-29 | 2004-03-30 | 주식회사 엘지화학 | 반도체 층간 절연용 재료 및 이를 이용한 반도체 장치 |
KR100405312B1 (ko) * | 2001-04-11 | 2003-11-12 | 주식회사 엘지 | 유기실리케이트 중합체 및 이를 함유하는 저유전 절연막 |
KR100451044B1 (ko) * | 2001-06-07 | 2004-10-02 | 주식회사 엘지화학 | 유기실리케이트 중합체의 제조방법, 및 이를 이용한절연막의 제조방법 |
-
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101292343B (zh) * | 2005-09-01 | 2012-10-31 | 飞思卡尔半导体公司 | 在双镶嵌互连上的覆盖层的形成 |
CN101517001B (zh) * | 2006-09-18 | 2011-11-09 | Lg化学株式会社 | 用于制备保护膜的低温快速固化组合物、由该组合物制备的保护膜和包括该保护膜的基板 |
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US20050266699A1 (en) | 2005-12-01 |
EP1392761A1 (en) | 2004-03-03 |
WO2002098955A1 (en) | 2002-12-12 |
CN100422240C (zh) | 2008-10-01 |
JP3819391B2 (ja) | 2006-09-06 |
KR20020094098A (ko) | 2002-12-18 |
US20030181750A1 (en) | 2003-09-25 |
US7238627B2 (en) | 2007-07-03 |
JP2004533517A (ja) | 2004-11-04 |
US6933360B2 (en) | 2005-08-23 |
KR100451044B1 (ko) | 2004-10-02 |
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