JP4549781B2 - 新規のシロキサン樹脂及びこれを用いた半導体層間絶縁膜 - Google Patents
新規のシロキサン樹脂及びこれを用いた半導体層間絶縁膜 Download PDFInfo
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- JP4549781B2 JP4549781B2 JP2004250188A JP2004250188A JP4549781B2 JP 4549781 B2 JP4549781 B2 JP 4549781B2 JP 2004250188 A JP2004250188 A JP 2004250188A JP 2004250188 A JP2004250188 A JP 2004250188A JP 4549781 B2 JP4549781 B2 JP 4549781B2
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- carbon atoms
- insulating film
- interlayer insulating
- semiconductor interlayer
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- 239000004065 semiconductor Substances 0.000 title claims description 65
- 239000011229 interlayer Substances 0.000 title claims description 61
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 71
- 239000000126 substance Substances 0.000 claims description 58
- 239000000178 monomer Substances 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
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- 239000010408 film Substances 0.000 description 59
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- 238000004519 manufacturing process Methods 0.000 description 8
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- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- -1 aryl sulfonic acid Chemical compound 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910008051 Si-OH Inorganic materials 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 229910006358 Si—OH Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02203—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being porous
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
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Description
また、本発明は、前記シロキサン系樹脂を5〜70質量%の有機溶媒に溶かして選択的に気孔形成物質を追加した、半導体層間絶縁膜形成用組成物に関する。
ハロゲン原子としては、特に限定されないが、フッ素原子、塩素原子、臭素原子およびヨウ素原子などが好ましく挙げられる。炭素数1〜5のアルコキシ基としては、特に限定されないが、メトキシ基、エトキシ基、プロポキシ基およびブトキシ基などが好ましく挙げられる。
実施例1では、5種類のモノマーを用意し、それぞれモノマー(A)、モノマー(B)、モノマー(C)、モノマー(D)、モノマー(E)とした。
2,4,6,8−テトラメチル−2,4,6,8−テトラビニールシクロテトラシロキサン29.014mmol(10.0g)とキシレン溶液に溶解されているプラチナム(O)−1,3−ジビニール−1,1,3,3−テトラメチルジシロキサン化合物0.164gをフラスコに仕込んだ後、ジエチルエーテル300mlを入れて希釈し、反応容器を−78℃に降温した後、トリクロロシラン127.66mmol(17.29g)を徐々に加え、その後反応温度を徐々に常温まで昇温した。その後、常温で40時間反応を行わせ、0.1torr(13.33Pa)程度の減圧下で揮発性物質を除去した。ここにヘキサン100mlを加え、1時間攪拌した後、セライトを介してフィルタリングして溶液を得、この溶液をさらに0.1torr(13.33Pa)程度の減圧下でヘキサンを除去して下記化学式8に示す液体化合物を製造した。
(実施例1−2:シロキサン系モノマー(B)、および(C)の合成)
モノマー(B)の2,4,4,6−テトラメトキシ−2,2,6,6−テトラメチル−2,4,6−トリスシラヘプタンとモノマー(C)の2,2,4,4,6,6−ヘキサメトキシ−2,6−ジメチル−2,4,6−トリスシラヘプタンは、銅触媒の下で250〜300℃でα−クロロメチルシランとシリコン(Si)金属との直接反応方法によって製造された。
下記表1に示す組成でモノマーをフラスコに投入し、総投入モノマーの15倍程度の質量のテトラヒドロフランを入れてモノマーを希釈した後、フラスコの内部温度を−78℃まで降温した。−78℃で表1に記載の量で塩酸及び水を入れ、反応器の温度を70℃まで徐々に昇温した。その後、70℃で反応を20時間行った。反応溶液を漏斗に移した後、最初に入れたテトラヒドロフランと同量のジエチルエーテルとテトラヒドロフランとを添加し、総溶媒の1/10倍程度の水で3回洗浄した後、揮発性物質を除去して白色粉末状の重合体を得た。
実施例2で製造されたシロキサン系樹脂のSi−OH含量、Si−OCH3量、Si−CH3、およびSi−H含量の測定値は下記表2の通りである。
実施例2で製造されたシロキサン系樹脂に気孔形成物質としてのヘプタキス[2,3,6−トリ−O−メトキシ]−β−シクロデキストリンを下記表3のような質量分率(mass%)で混合し、プロピレングリコールメチルエーテルアセテートを、半導体層間絶縁膜形成用組成物全体のうち固形分の質量が25質量分率(mass%)となるように添加した後、混合溶液を3000RPMで30秒間シリコン基板上にスピンコーティングした。
ホウ素でドープされたP型のシリコンウェーハ上にシリコン熱酸化膜を3000Åの厚さに塗布し、その後金属蒸発器でチタニウム100Å、アルミニウム薄膜2000Å、チタニウム100Åを蒸着した後、表4に示される組成で半導体層間絶縁膜形成用組成物をコートして低誘電率の半導体層間絶縁膜を作製した。その後、電極の直径が1mmに設計されたハードマスクを用いて、1mmの直径を有する円形のチタニウム100Å、アルミニウム薄膜5000Åを蒸着してMIM(metal−insulator−metal)構造の誘電率測定用半導体層間絶縁膜を完成した。このような半導体層間絶縁膜を、プローブステーション(Micromanipulation Company株式会社製;micromanipulatior 6200 probe station)が装着された(HP社製;PRECISION LCR METER HP4284A)を用いて約100kHzの周波数で静電容量を測定した。誘電率を計算するために半導体層間絶縁膜の厚さをプリズムカプラで測定して次の計算式によって誘電率を計算した。
硬度及びモジュラスの測定は、実施例4で製造された半導体層間絶縁膜をMTS社のナノインデンターIIを用いて定量的に分析した。また、各サンプルに対して信頼度を確認するために、6ポイントを圧入(indent)して平均値からそれぞれの硬度及びモジュラスを求めた。前記の半導体層間絶縁膜を用いてナノインデンターで圧入し始めた後、圧入深さが半導体層間絶縁膜全圧の10%となったとき、半導体層間絶縁膜の硬度及びモジュラスを求めた結果値は表5の通りである。この際、半導体層間絶縁膜の厚さはプリズムカプラを用いて測定した。
Claims (11)
- 下記(a)〜(d)を満たすシロキサン系樹脂;
(a)下記化学式1で表わされるモノマー、又は
下記化学式1で表わされるモノマーと、下記化学式2〜6で表わされる化合物よりなる群から選択される少なくとも一種のモノマーと、
を有機溶媒の下で、酸触媒又は塩基触媒と、水と、を用いて加水分解反応及び縮合重合されてなる;
(b)熱硬化性を有する;
(c)重量平均分子量が3,000〜300,000である;
(d)末端基の総数に対して、5〜50モル%がSi−OR基である;
- 前記水のモル比は、前記化学式1〜6で表されるモノマーに対して1:1〜1:1000であり、加水分解反応及び縮合重合は、前記化学式1〜6モノマーの質量に対して15倍の質量の溶媒中で行うことを特徴とする請求項1記載のシロキサン系樹脂。
- 前記化学式1で表わされるモノマーと前記化学式2〜6で表わされるモノマーとのモル比は、順番に1:99〜99:1の範囲であることを特徴とする請求項1または2記載のシロキサン系樹脂。
- 下記(e)および(f)を満たす半導体層間絶縁膜形成用組成物;
(e)請求項1〜3のいずれかに記載のシロキサン系樹脂と、第二の有機溶媒とを含む;
(f)前記第二の有機溶媒の含有量は、半導体層間絶縁膜形成組成物の全質量に対して5〜70質量%である。 - 組成成分として気孔形成物質が追加されることを特徴とする請求項4記載の半導体層間絶縁膜形成用組成物。
- 前記気孔形成物質の組成比が全体固形分の質量に対して1〜70質量%であることを特徴とする請求項5記載の半導体層間絶縁膜形成用組成物。
- 前記気孔形成物質がシクロデキストリン、ポリカプロラクトン又はその誘導体からなる群より選択される少なくとも一種であることを特徴とする請求項5または6記載の半導体層間絶縁膜形成用組成物。
- 請求項4〜7のいずれかに記載の半導体層間絶縁膜形成用組成物をシリコン基板上にコートした後、熱硬化させる段階を含む半導体層間絶縁膜の形成方法。
- 前記熱硬化は温度150〜600℃の条件で1〜150分間行うことを特徴とする請求項8記載の半導体層間絶縁膜の形成方法。
- 請求項8又は9に記載の半導体層間絶縁膜の形成方法により形成されてなる半導体層間絶縁膜。
- フィルム全体に気孔が形成されていることを特徴とする請求項10記載の半導体層間絶縁膜。
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- 2004-08-20 DE DE200460000964 patent/DE602004000964T2/de active Active
- 2004-08-30 JP JP2004250188A patent/JP4549781B2/ja active Active
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Publication number | Publication date |
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US7108922B2 (en) | 2006-09-19 |
CN100455619C (zh) | 2009-01-28 |
CN1597738A (zh) | 2005-03-23 |
EP1510537B1 (en) | 2006-05-24 |
DE602004000964D1 (de) | 2006-06-29 |
JP2005076031A (ja) | 2005-03-24 |
EP1510537A1 (en) | 2005-03-02 |
DE602004000964T2 (de) | 2007-01-18 |
US20050049382A1 (en) | 2005-03-03 |
KR20050024721A (ko) | 2005-03-11 |
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