US20010010840A1 - Electrically insulating resin composition and method for forming thin film therefrom - Google Patents
Electrically insulating resin composition and method for forming thin film therefrom Download PDFInfo
- Publication number
- US20010010840A1 US20010010840A1 US09/765,199 US76519901A US2001010840A1 US 20010010840 A1 US20010010840 A1 US 20010010840A1 US 76519901 A US76519901 A US 76519901A US 2001010840 A1 US2001010840 A1 US 2001010840A1
- Authority
- US
- United States
- Prior art keywords
- electrically insulating
- insulating thin
- component
- film
- resin composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 239000010409 thin film Substances 0.000 title claims abstract description 34
- 239000011342 resin composition Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 25
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 44
- 239000010703 silicon Substances 0.000 claims abstract description 44
- 239000011347 resin Substances 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 229920003209 poly(hydridosilsesquioxane) Polymers 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- HJMCXQUNIYVGLH-UHFFFAOYSA-N hex-1-enyl-[hex-1-enyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CCCCC=C[Si](C)(C)O[Si](C)(C)C=CCCCC HJMCXQUNIYVGLH-UHFFFAOYSA-N 0.000 claims description 6
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000009987 spinning Methods 0.000 description 12
- 230000001939 inductive effect Effects 0.000 description 10
- 229910004726 HSiO3/2 Inorganic materials 0.000 description 8
- -1 siloxane units Chemical group 0.000 description 7
- 238000010894 electron beam technology Methods 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000010453 quartz Substances 0.000 description 6
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 5
- 125000006038 hexenyl group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- FJWRGPWPIXAPBJ-UHFFFAOYSA-N diethyl(dimethyl)silane Chemical compound CC[Si](C)(C)CC FJWRGPWPIXAPBJ-UHFFFAOYSA-N 0.000 description 1
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
-
- 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
- H01L21/02134—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 the material comprising hydrogen silsesquioxane, e.g. HSQ
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- 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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
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- 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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
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- 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
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
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- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
- H01L21/3122—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
- H01L21/3122—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds
- H01L21/3124—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds layers comprising hydrogen silsesquioxane
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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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- 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 an electrically insulating thin-film-forming resin composition, and to a method for forming an electrically insulating thin film. More particularly, it relates to an electrically insulating thin-film-forming resin composition with which it is possible to form an electrically insulating thin film having a low dielectric constant, and to a method for efficiently forming an electrically insulating thin film having a low dielectric constant on the surface of an electronic device.
- Examples of a method for forming an electrically insulating thin film on the surface of an electronic device include a method in which the surface of an electronic device is coated with a hydrogen silsesquioxane resin solution, the solvent is evaporated off, and the surface is then heated at 150 to 1000° C. (see Japanese Laid-Open Patent Application S63-144525), and a method in which the surface of an electronic device is coated with a solution of a hydrogen silsesquioxane resin and a platinum or rhodium catalyst, the solvent is evaporated off, and the surface is then heated at 150 to 1000° C. (see Japanese Laid-Open Patent Application S63-144524).
- Japanese Laid-Open Patent Application H10-279687 proposes a method in which the surface of an electronic device is coated with a solution composed of a hydrogen silsesquioxane resin and two types of solvent with different boiling points or affinity to the resin, after which part of the solvent is evaporated, and the surface is heated to evaporate the solvent either during or after the crosslinking of the resin, thereby forming a porous electrically insulating crosslinked thin film.
- a porous electrically insulating thin film generally has poor mechanical strength and is susceptible to infiltration and attack by a variety of chemicals, and therefore cannot sufficiently stand up to the next-generation of multilayer wiring processes, and particularly to a copper dual damascene process, making such films impractical.
- silicon atom-bonded hydrogen atoms must be present in the hydrogen silsesquioxane resin, and consequently the silicon atom-bonded hydrogen atoms in the thin film react due to the heat, various chemicals, or plasma encountered in the various steps following the formation of the thin film, such as the multilayer wiring of an electronic device, which further raises the density of the thin film and drives up the dielectric constant.
- the present invention is an electrically insulating thin-film-forming resin composition
- A an inorganic or organic electrically insulating resin having silicon atom-bonded hydrogen atoms
- B a compound having groups able to react with the silicon atom-bonded hydrogen atoms in component (A) and having a boiling point under atmospheric pressure of at least 250° C.
- C a solvent
- the present invention is an electrically insulating thin-film-forming resin composition
- A an inorganic or organic electrically insulating resin having silicon atom-bonded hydrogen atoms
- B a compound having groups able to react with the silicon atom-bonded hydrogen atoms in component (A) and having a boiling point under atmospheric pressure of at least 250° C.
- C a solvent
- the electrically insulating resin of component A is an inorganic or organic electrically insulating resin having silicon atom-bonded hydrogen atoms, examples of which include inorganic resins that are silica precursor resins such as a hydrogen silsesquioxane resin or a partial hydrolyzate of an alkoxysilane having silicon atom-bonded hydrogen atoms; and organic resins having silicon atom-bonded hydrogen atoms, such as polyimide resins, fluorocarbon resins, benzocyclobutene resins, fluorinated polyallyl ether resins, and mixtures of two or more of these.
- silica precursor resins such as a hydrogen silsesquioxane resin or a partial hydrolyzate of an alkoxysilane having silicon atom-bonded hydrogen atoms
- organic resins having silicon atom-bonded hydrogen atoms such as polyimide resins, fluorocarbon resins, benzocyclobutene resins, fluorinated polyallyl ether resins,
- a silica resin precursor that forms silica upon curing is preferable as the electrically insulating resin of component A, and a hydrogen silsesquioxane resin is particularly favorable.
- This hydrogen silsesquioxane resin described by average structure formula (HSiO 3/2 ), is a polymer whose main skeleton consists of trifunctional siloxane units expressed by formula HSiO 3/2 .
- the groups at the molecular chain terminals of this hydrogen silsesquioxane resin include the hydroxyl group, the trimethylsiloxy group and other triorganosiloxy groups, and the dimethylhydrogensiloxy group and other triorganohydrogensiloxy groups.
- An example of a method for preparing this hydrogen silsesquioxane resin is the hydrolysis and polycondensation of trichlorosilane.
- the compound of component (B) has groups able to react with the silicon atom-bonded hydrogen atoms in component (A). Examples of these groups able to react with silicon atom-bonded hydrogen atoms include aliphatic unsaturated hydrocarbon groups, alkoxy groups, and silanol groups, with aliphatic unsaturated hydrocarbon groups being particularly favorable.
- the compound of component (B) also has a boiling point under atmospheric pressure of at least 250° C. This is because a compound whose boiling point under atmospheric pressure is lower than 250° C. will evaporate before fully reacting with the silicon atom-bonded hydrogen atoms in component A, so the object of the present invention cannot be achieved.
- component (B) There are no restrictions on the specific inductive capacity of component (B), but it is preferable to choose a compound with a low specific inductive capacity because the dielectric constant of the resulting electrically insulating resin can be further lowered.
- component (B) is contained in the present composition, but the amount is preferably such that there will be at least an equivalent amount of silicon atom-bonded hydrogen atoms in component (A) with respect to the groups able to react with silicon atom-bonded hydrogen atoms in component (B).
- An amount such that there are at least five equivalents of silicon atom-bonded hydrogen atoms in component (A) per reactive groups in component (B) is particularly favorable.
- solvents suitable as component C include toluene, xylene, and other aromatic solvents; hexane, heptane, octane, and other aliphatic solvents; methyl ethyl ketone, methyl isobutyl ketone, and other ketone-based solvents; butyl acetate, isoamyl acetate, and other aliphatic ester-based solvents; hexamethyldisiloxane, 1,1,3,3-tetramethyldisiloxane, and other linear methylsiloxanes, 1,1,3,3,5,5,7,7-octamethylcyclotetrasiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, and other cyclic siloxanes; and silane compounds such as
- component (C) is contained in the present composition, but the amount is preferably at least 50 weight parts per 100 weight parts of component A. This is because it will tend to be difficult to apply a thin coating of the resulting resin composition over the surface of a base material such as an electronic device if component (C) content is below the lower limit of the above range.
- the present composition contains (D) a catalyst which acts as a crosslinking accelerator to promote the reaction between the silicon atom-bonded hydrogen atoms in component (A) and the groups in component (B) capable of reacting with the silicon atom-bonded hydrogen atoms.
- a catalyst which acts as a crosslinking accelerator to promote the reaction between the silicon atom-bonded hydrogen atoms in component (A) and the groups in component (B) capable of reacting with the silicon atom-bonded hydrogen atoms.
- component (D) allows component (A) in the present composition to be crosslinked at a relatively low temperature.
- this catalyst of component (D) examples include particulate platinum, chloroplatinic acid, an alcohol solution of chloroplatinic acid, an olefin complex of platinum, an alkenylsiloxane complex of platinum, a carbonyl complex of platinum, and other such platinum-based catalysts; rhodium catalysts; dibutyltin diacetate, dibutyltin dioctoate, and other such tin-based catalysts; and tetrabutyl titanate, tetrapropyl titanate, and other such titanium-based catalysts.
- the amount in which component (D) is contained in the present composition is preferably between 1 and 1000 weight parts per million weight parts of component (A) and component (B) combined.
- a sensitizer may also be added if the present composition is to be crosslinked solely by irradiation with high-energy rays.
- the method of the present invention for forming an electrically insulating thin film is characterized in that the surface of an electronic device is coated with the above-mentioned electrically insulating thin-film-forming resin composition and all or part of the solvent is evaporated, after which the electrically insulating organic resin contained in the composition is crosslinked by heating and/or irradiation with high-energy rays.
- Examples of methods for coating the electronic device surface with the electrically insulating thin-film-forming resin composition include spin coating, dip coating, spray coating, and flow coating.
- the electrically insulating resin in the above-mentioned composition is crosslinked by heating and/or irradiation with high-energy rays.
- heating methods include the use of a heating furnace or a hot plate.
- high-energy rays examples include ultraviolet rays, infrared rays, X-rays, and an electron beam.
- the use of an electron beam is particularly favorable because component A can be thoroughly crosslinked.
- the electrically insulating thin-film-forming resin composition and the method for forming an electrically insulating thin film of the present invention will now be described in detail through examples.
- the degree of crosslinking in the examples was determined by measuring the percent of residual SiH in the electrically insulating thin film by Fourier transform UV absorption spectrographic analysis.
- the percentage residual SiH percentage in the electrically insulating thin film is based on the amount of silicon atom-bonded hydrogen atoms remaining in the cured electrically insulating thin film when the amount of silicon atom-bonded hydrogen atoms contained in the electrically insulating thin-film-forming resin composition immediately after spin coating on a silicon wafer is 100%.
- the specific inductive capacity of the electrically insulating thin film was measured by an impedance analyzer (sandwiched aluminum electrode type) at 25° C. and 1 MHz using an electrically insulating thin film formed on a silicon wafer with a volumetric resistivity of 10 ⁇ 2 ⁇ cm or less.
- This composition was then spin coated on a silicon wafer for 5 seconds of pre-spinning (500 rpm) and 10 seconds of main spinning (3000 rpm), after which the coating was irradiated with an electron beam (300 Mrad) accelerated at 165 kV, forming an electrically insulating thin film with a thickness of 750 nm, a residual SiH content of 70%, and a specific inductive capacity of 2.5.
- This composition was then spin coated on a silicon wafer for 5 seconds of pre-spinning (500 rpm) and 10 seconds of main spinning (3000 rpm), after which the coating was irradiated with an electron beam (300 Mrad) accelerated at 165 kV, and was then heated for 1 hour in a quartz furnace (400° C.) under a nitrogen atmosphere, forming an electrically insulating thin film with a thickness of 720 nm, a residual SiH content of 40%, and a specific inductive capacity of 2.4.
- This composition was then spin coated on a silicon wafer for 5 seconds of pre-spinning (500 rpm) and 10 seconds of main spinning (3000 rpm), after which the coating was heated for 1 hour in a quartz furnace (250° C.) under a nitrogen atmosphere and then heated for another hour in a quartz furnace (400° C.) under a nitrogen atmosphere, forming an electrically insulating thin film with a thickness of 710 nm, a residual SiH content of 40%, and a specific inductive capacity of 2.4.
- This composition was then spin coated on a silicon wafer for 5 seconds of pre-spinning (500 rpm) and 10 seconds of main spinning (3000 rpm), after which the coating was irradiated with an electron beam (300 Mrad) accelerated at 165 kV, and was then heated for 1 hour in a quartz furnace (400° C.) under a nitrogen atmosphere, forming an electrically insulating thin film with a thickness of 750 nm, a residual SiH content of 30%, and a specific inductive capacity of 2.3.
- This composition was then applied by spin coating over a silicon wafer for 5 seconds of pre-spinning (500 rpm) and 10 seconds of main spinning (3000 rpm), after which the coating was irradiated with an electron beam (300 Mrad) accelerated at 165 kV, and was then heated for 1 hour in a quartz furnace (450° C.) under a nitrogen atmosphere, forming an electrically insulating thin film with a thickness of 800 nm, a residual SiH content of 40%, and a specific inductive capacity of 2.4.
- An electrically insulating thin-film-forming resin composition was prepared composed of 22 wt % hydrogen silsesquioxane resin described by average structure formula (HSiO 3/2 ) and 78 wt % 1,1,1,3,3,5,5,5-octamethyltrisiloxane. This composition was then spin coated on a silicon wafer for 5 seconds of pre-spinning (500 rpm) and 10 seconds of main spinning (3000 rpm), after which the coating was heated for 1 minute each on 150° C., 250° C., and 350° C.
- pre-spinning 500 rpm
- main spinning main spinning
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Priority Applications (1)
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US10/315,337 US6764718B2 (en) | 2000-01-31 | 2002-12-09 | Method for forming thin film from electrically insulating resin composition |
Applications Claiming Priority (2)
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JP2000022624A JP2001214127A (ja) | 2000-01-31 | 2000-01-31 | 電気絶縁性薄膜形成性樹脂組成物、および電気絶縁性薄膜の形成方法 |
JP2000-022624 | 2000-01-31 |
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US10/315,337 Division US6764718B2 (en) | 2000-01-31 | 2002-12-09 | Method for forming thin film from electrically insulating resin composition |
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US20010010840A1 true US20010010840A1 (en) | 2001-08-02 |
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US09/765,199 Abandoned US20010010840A1 (en) | 2000-01-31 | 2001-01-18 | Electrically insulating resin composition and method for forming thin film therefrom |
US10/315,337 Expired - Fee Related US6764718B2 (en) | 2000-01-31 | 2002-12-09 | Method for forming thin film from electrically insulating resin composition |
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US10/315,337 Expired - Fee Related US6764718B2 (en) | 2000-01-31 | 2002-12-09 | Method for forming thin film from electrically insulating resin composition |
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US (2) | US20010010840A1 (de) |
EP (1) | EP1122768A3 (de) |
JP (1) | JP2001214127A (de) |
KR (1) | KR20010078193A (de) |
SG (1) | SG88811A1 (de) |
TW (1) | TWI254069B (de) |
Cited By (3)
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US20030010961A1 (en) * | 2001-07-16 | 2003-01-16 | Fujitsu Limited | Composition for forming low dielectric constant insulating film, method of forming insulating film using the composition and electronic parts having the insulating film produced thereby |
US20090309195A1 (en) * | 2005-08-19 | 2009-12-17 | Rhodia Chimie | Low Dielectric Constant Silicon Coating, Method for the Preparation and Application thereof to Integrated Circuits |
CN109689735A (zh) * | 2016-09-30 | 2019-04-26 | 美国陶氏有机硅公司 | 桥联有机硅树脂、膜、电子器件以及相关方法 |
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US7622378B2 (en) * | 2005-11-09 | 2009-11-24 | Tokyo Electron Limited | Multi-step system and method for curing a dielectric film |
US8956457B2 (en) * | 2006-09-08 | 2015-02-17 | Tokyo Electron Limited | Thermal processing system for curing dielectric films |
US20090075491A1 (en) * | 2007-09-13 | 2009-03-19 | Tokyo Electron Limited | Method for curing a dielectric film |
US7858533B2 (en) * | 2008-03-06 | 2010-12-28 | Tokyo Electron Limited | Method for curing a porous low dielectric constant dielectric film |
US20090226694A1 (en) * | 2008-03-06 | 2009-09-10 | Tokyo Electron Limited | POROUS SiCOH-CONTAINING DIELECTRIC FILM AND A METHOD OF PREPARING |
US7977256B2 (en) | 2008-03-06 | 2011-07-12 | Tokyo Electron Limited | Method for removing a pore-generating material from an uncured low-k dielectric film |
US20090226695A1 (en) * | 2008-03-06 | 2009-09-10 | Tokyo Electron Limited | Method for treating a dielectric film with infrared radiation |
US20100065758A1 (en) * | 2008-09-16 | 2010-03-18 | Tokyo Electron Limited | Dielectric material treatment system and method of operating |
US8895942B2 (en) * | 2008-09-16 | 2014-11-25 | Tokyo Electron Limited | Dielectric treatment module using scanning IR radiation source |
US9017933B2 (en) * | 2010-03-29 | 2015-04-28 | Tokyo Electron Limited | Method for integrating low-k dielectrics |
TWI747956B (zh) * | 2016-09-30 | 2021-12-01 | 美商道康寧公司 | 橋接聚矽氧樹脂、膜、電子裝置及相關方法 |
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US3418353A (en) * | 1964-12-28 | 1968-12-24 | Gen Electric | Alkylpolysiloxane fluids |
JPS58163652A (ja) * | 1982-03-25 | 1983-09-28 | トーレ・シリコーン株式会社 | 連続的な異相構造を有するシリコ−ン1体成形物,およびその製造方法 |
US4756977A (en) | 1986-12-03 | 1988-07-12 | Dow Corning Corporation | Multilayer ceramics from hydrogen silsesquioxane |
US4822697A (en) | 1986-12-03 | 1989-04-18 | Dow Corning Corporation | Platinum and rhodium catalysis of low temperature formation multilayer ceramics |
US5393521A (en) * | 1989-12-21 | 1995-02-28 | Dep Corporation | Hair treatments utilizing polymethylalkylsiloxanes |
JP3174416B2 (ja) * | 1992-12-10 | 2001-06-11 | ダウ・コ−ニング・コ−ポレ−ション | 酸化ケイ素膜の形成方法 |
JP3406646B2 (ja) * | 1993-06-29 | 2003-05-12 | 東レ・ダウコーニング・シリコーン株式会社 | オルガノポリシロキサンおよびその製造方法 |
JP3466238B2 (ja) * | 1993-08-18 | 2003-11-10 | 東レ・ダウコーニング・シリコーン株式会社 | オルガノポリシロキサンおよびその製造方法 |
US5635240A (en) * | 1995-06-19 | 1997-06-03 | Dow Corning Corporation | Electronic coating materials using mixed polymers |
JP3415741B2 (ja) | 1997-03-31 | 2003-06-09 | 東レ・ダウコーニング・シリコーン株式会社 | 電気絶縁性薄膜形成用組成物および電気絶縁性薄膜の形成方法 |
JP3354431B2 (ja) | 1997-03-31 | 2002-12-09 | 東レ・ダウコーニング・シリコーン株式会社 | 電気絶縁性薄膜形成用組成物および電気絶縁性薄膜の形成方法 |
JP3210601B2 (ja) | 1997-05-28 | 2001-09-17 | 東レ・ダウコーニング・シリコーン株式会社 | 半導体装置及びその製造方法 |
EP0881668A3 (de) * | 1997-05-28 | 2000-11-15 | Dow Corning Toray Silicone Company, Ltd. | Abscheidung eines elektrisch isolierenden Dünnfilms mit einer niedrigen Dielektrizitätskonstante |
JP3208100B2 (ja) | 1997-10-30 | 2001-09-10 | 東レ・ダウコーニング・シリコーン株式会社 | 電気絶縁性薄膜の形成方法 |
DE19816921A1 (de) * | 1998-04-16 | 1999-10-21 | Wacker Chemie Gmbh | Verfahren für kontinuierliche polymeranaloge Umsetzungen |
EP1035183B1 (de) * | 1998-09-25 | 2009-11-25 | JGC Catalysts and Chemicals Ltd. | Flüssige beschichtungszusammensetzung für silicabeschichtung mit niedriger durchlössigkeit und mit dieser zusammensetzung beschichtetes substrat |
US6252030B1 (en) * | 1999-03-17 | 2001-06-26 | Dow Corning Asia, Ltd. | Hydrogenated octasilsesquioxane-vinyl group-containing copolymer and method for manufacture |
JP3543669B2 (ja) * | 1999-03-31 | 2004-07-14 | 信越化学工業株式会社 | 絶縁膜形成用塗布液及び絶縁膜の形成方法 |
US6541107B1 (en) * | 1999-10-25 | 2003-04-01 | Dow Corning Corporation | Nanoporous silicone resins having low dielectric constants |
US6387997B1 (en) * | 1999-11-10 | 2002-05-14 | Ppg Industries Ohio, Inc. | Solvent-free film-forming compositions, coated substrates and method related thereto |
US6143360A (en) * | 1999-12-13 | 2000-11-07 | Dow Corning Corporation | Method for making nanoporous silicone resins from alkylydridosiloxane resins |
-
2000
- 2000-01-31 JP JP2000022624A patent/JP2001214127A/ja active Pending
-
2001
- 2001-01-18 US US09/765,199 patent/US20010010840A1/en not_active Abandoned
- 2001-01-29 EP EP20010300767 patent/EP1122768A3/de not_active Withdrawn
- 2001-01-30 SG SG200100431A patent/SG88811A1/en unknown
- 2001-01-31 TW TW90101887A patent/TWI254069B/zh not_active IP Right Cessation
- 2001-01-31 KR KR1020010004514A patent/KR20010078193A/ko not_active Application Discontinuation
-
2002
- 2002-12-09 US US10/315,337 patent/US6764718B2/en not_active Expired - Fee Related
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030010961A1 (en) * | 2001-07-16 | 2003-01-16 | Fujitsu Limited | Composition for forming low dielectric constant insulating film, method of forming insulating film using the composition and electronic parts having the insulating film produced thereby |
US7060909B2 (en) * | 2001-07-16 | 2006-06-13 | Fujitsu Limited | Composition for forming low dielectric constant insulating film, method of forming insulating film using the composition and electronic parts having the insulating film produced thereby |
US20090309195A1 (en) * | 2005-08-19 | 2009-12-17 | Rhodia Chimie | Low Dielectric Constant Silicon Coating, Method for the Preparation and Application thereof to Integrated Circuits |
US8080286B2 (en) | 2005-08-19 | 2011-12-20 | Bluestar Silicones France Sas | Low dielectric constant silicon coating, method for the preparation and application thereof to integrated circuits |
CN109689735A (zh) * | 2016-09-30 | 2019-04-26 | 美国陶氏有机硅公司 | 桥联有机硅树脂、膜、电子器件以及相关方法 |
Also Published As
Publication number | Publication date |
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TWI254069B (en) | 2006-05-01 |
US6764718B2 (en) | 2004-07-20 |
KR20010078193A (ko) | 2001-08-20 |
JP2001214127A (ja) | 2001-08-07 |
SG88811A1 (en) | 2002-05-21 |
EP1122768A3 (de) | 2003-08-27 |
EP1122768A2 (de) | 2001-08-08 |
US20030091748A1 (en) | 2003-05-15 |
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Owner name: DOW CORNING TORAY SILICONE COMPANY, LTD., JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:NAKAMURA, TAKASHI;SAWA, KIYOTAKA;KOBAYASHI, AKIHIO;AND OTHERS;REEL/FRAME:011524/0442 Effective date: 20001225 |
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