CN1060861A - 增强聚酰亚胺对活性金属的粘合力的方法 - Google Patents
增强聚酰亚胺对活性金属的粘合力的方法 Download PDFInfo
- Publication number
- CN1060861A CN1060861A CN91109639A CN91109639A CN1060861A CN 1060861 A CN1060861 A CN 1060861A CN 91109639 A CN91109639 A CN 91109639A CN 91109639 A CN91109639 A CN 91109639A CN 1060861 A CN1060861 A CN 1060861A
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- Prior art keywords
- monomer
- silane
- polyimide film
- metal
- saturated hydrocarbyl
- 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.)
- Granted
Links
- 229920001721 polyimide Polymers 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 46
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 29
- 239000002184 metal Substances 0.000 title claims abstract description 29
- 239000004642 Polyimide Substances 0.000 title claims description 23
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 22
- 239000010703 silicon Substances 0.000 claims abstract description 22
- 229920001577 copolymer Polymers 0.000 claims abstract description 12
- 239000012528 membrane Substances 0.000 claims abstract description 10
- 238000007711 solidification Methods 0.000 claims abstract description 3
- 230000008023 solidification Effects 0.000 claims abstract description 3
- 229910000077 silane Inorganic materials 0.000 claims description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 58
- 239000000178 monomer Substances 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical group CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 claims description 7
- 229920005575 poly(amic acid) Polymers 0.000 claims description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 5
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 230000001464 adherent effect Effects 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 2
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 45
- -1 oxydiphenyl amine Chemical class 0.000 description 24
- 150000001721 carbon Chemical group 0.000 description 11
- 239000004743 Polypropylene Substances 0.000 description 9
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- 230000008859 change Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920002274 Nalgene Polymers 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
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- 238000009413 insulation Methods 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 239000002253 acid Substances 0.000 description 2
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical compound [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 239000012212 insulator Substances 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000003870 refractory metal Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- DVJBLMMLJCYICB-UHFFFAOYSA-N C=1C=CC=CC=1[SiH](N(C)C)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1[SiH](N(C)C)C1=CC=CC=C1 DVJBLMMLJCYICB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- DMLSHGGAICSCEF-UHFFFAOYSA-N N-methyl-N-phenylsilylmethanamine Chemical compound CN(C)[SiH2]c1ccccc1 DMLSHGGAICSCEF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000006159 dianhydride group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- 239000012442 inert solvent Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HZBAVWLZSLOCFR-UHFFFAOYSA-N oxosilane Chemical compound [SiH2]=O HZBAVWLZSLOCFR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000005360 phosphosilicate glass Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- FVBUAEGBCNSCDD-UHFFFAOYSA-N silicide(4-) Chemical compound [Si-4] FVBUAEGBCNSCDD-UHFFFAOYSA-N 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- 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
- H01L21/02219—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 nitrogen
- H01L21/02222—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 nitrogen the compound being a silazane
-
- 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
- H01L21/02205—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
- H01L21/02211—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 being a silane, e.g. disilane, methylsilane or chlorosilane
-
- 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
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Abstract
为了改进聚酰亚胺膜对底层金属表面的粘合力,
将能固化成硅倍半环氧乙烷共聚物的有机溶液涂到
金属表面上。在同时固化过程中形成聚酰亚胺膜和
共聚物膜。
Description
本发明涉及改进聚酰亚胺膜对底层金属表面(如带有金属镀敷图案的底板,例如铜版)的粘合力的方法。
已知聚酰亚胺前体(如聚酰胺酸)热固化形成的聚酰亚胺可在半导体器件中用作钝化电介质。例如参见1986年5月26日授予Linde等人的美国专利第4,590,258号。然而,由于聚酰亚胺对金属表面的粘合力很差,带来了界面处水分渗透增加和氧化作用增加的问题。由此导致丧失钝化功能。
改进各种聚合物基底材料的粘合力的许多方法在本技术领域中是已知的。例如1978年7月25日授予Lesaicherre等人的美国专利第4,103,045号,描述了将选定的氨基硅烷或环多硅氧氮烷(cyclopolysiloxazane)的溶液涂在无机氧化物层上使光刻胶聚合物与无机氧化物层粘合。类似地,1985年7月16日授予Ponjee等人的美国专利第4,529,618号中报导,在涂光刻胶聚合物之前,先用3-氨丙基三烷氧硅烷的水溶液处理无机材料。
制备硅倍半环氧乙烷(Silsesquioxane)聚合物以用作半导体器件中的绝缘层也是已知的。例如,在1987年6月24日公开的欧洲专利申请(公开号为第0,226,208号)介绍了在衬底上涂敷预聚物,然后在氧存在下在高于400℃的温度下加热以形成绝缘层的方法。该预聚物是使选定摩尔比的四烷氧硅烷、三烷氧硅烷和二烷氧硅烷的混合物进行水解和缩聚而制得的。
在1986年12月2日授予Nozue等人的美国专利4,4,626,556号中,报导了让水和三卤代硅烷反应以生成不含氨基的硅倍半环氧乙烷聚合物,该聚合物与受辐照时能产生具有交联反应活性物质的化合物一起构成混合物用于形成绝缘层。在1988年2月9日授予Clodgo等人的美国专利第4,723,978号中,公开了采用先从硅烷醇溶液制备改性的梯形硅倍半环氧乙烷聚合物,然后在氧等离子体中处理它以产生有机质玻璃绝缘层的方法。
然而,这些方法均未涉及用硅倍半环氧乙烷形成促进粘合的涂层,
针对这一背景情况,本发明提供使聚酰亚胺膜与底层金属表面粘合的改进方法。根据本发明,先将某种有机溶液涂到底层金属表面上,该溶液是由氨烷氧基硅烷单体、芳烷氧基硅烷或芳基硅氮烷单体及水在溶剂中反应制得的。然后,进行加热步骤以形成部分固化层,再涂上含有聚酰亚胺前体的溶液。进行第二次加热以同时形成固化的硅倍半环氧乙烷共聚物层和聚酰亚胺膜。在本发明的实施过程中,得到了固化的结构,在该结构中在聚酰亚胺和底层之间有很强的粘合,它既防潮又耐金属氧化,同时还提供了高度的热稳定性。该方法还可以用聚酰亚胺涂敷得到增加粘合力的涂层而不需要一套单独的完整的固化步骤。
根据本发明的方法,有机溶液被涂在带有金属镀敷图案的底层金属表面上,如金属膜或经过处理的半导体基底上。在这种情况下,典型的基底是包含有金属图案的绝缘体层。例如,该绝缘体层通常包括二氧化硅、氮化硅、回流磷硅酸盐玻璃或聚酰亚胺,例如从1,2,4,5-苯四酸二酐和氧联二苯胺、或二苯酮四羧酸二酐和氧联二苯胺和/或间苯二胺或本领域技术熟练人员已知的其它芳香族聚酰亚胺或聚酰胺-酰亚胺制备的聚酰亚胺。典型的金属包括过渡金属或过渡金属合金、高熔点金属或高熔点金属的硅化物等,例如,铜、铝、银、铬、铅、锡、金、Ⅳ主族金属、Ⅴ主族金属和Ⅵ主族金属,如钛和钨等等。
采用旋转涂敷等传统方式将有机溶液涂在底层表面上,根据所需要的厚度,可选旋转速度为约2,000-5,000转/分。该有机溶液是由氨烷氧基硅烷单体、芳烷氧基硅烷或芳基硅氮烷单体与水在溶剂中反应而制备的。合适的氨烷氧基硅烷单体包括由/式(A)表示的氨基三烷氧基硅烷:
其中,R1为氢原子;饱和烃基或氨基取代的(二或三氨基取代较好)饱和烃基,烃基有1至5个碳原子较好;或烷基取代的苯基或其衍生物,较好的烷基含有1至5个碳原子;其中,R2为饱和烃基(含2至6个碳原子较好)或烷基取代的(二烷基取代的较好)苯基或其衍生物,每个烷基含1至5个碳原子较好;其中R3为饱和烃基基,较好的是含1至8个碳原子的。另外,这些氨基三烷氧基硅烷的混合物也可以使用。
具有代表性的氨烷氧基硅烷单体包括下列物质:γ-氨丙基三甲氧基硅烷、γ-氨丙基三乙氧基硅烷、N-β-(氨乙基)-γ-氨丙基三甲氧基硅烷、N-β-(氨乙基)-γ-氨丙基三乙氧基硅烷、N-β-氨乙基-γ-氨丙基三(β-乙基六氧)硅烷、三甲氧甲硅烷基丙基二亚乙基三胺、(氨乙基氨甲基)苯乙基三甲氧基硅烷和α-三甲氧基甲硅烷基-β-(对-间-氨甲基)-苯基乙烷。
较好的氨烷氧基硅烷单体包括上面式(A)表示的氨基三烷氧基硅烷,其中R1为氢原子或含2或3个碳原子的饱和烃基或氨基取代的饱和烃基;其中R2为含3至6个碳原子的饱和烃基;其中R3为含1至4个碳原子的饱和烃基。
特别好的一组氨烷氧基硅烷单体包括下列氨基三烷氧基硅烷:γ-氨丙基三甲氧基硅烷、γ-氨丙基三乙氧基硅烷、N-β-(氨乙基)-γ-氨丙基三甲氧基硅烷和N-β-(氨乙基)-γ-氨丙基三乙氧基硅烷。
制备该有机溶液时所用的较好的芳烷氧基硅烷或芳基硅氮烷单体是由式(B)表示的:
其中,R4为未取代或取代的芳香族基团,如式(C)所示:
其中,n=0至6(0至3更好),如苄基或具有更高的官能度,R5为氢原子或饱和烃基,含1-8个碳原子较好,1至4个碳原子更好,如二甲苯基或莱基(mesitylyl);其中,Y为(OR6)或N(R7)2,其中R6为含1至5个碳原子的饱和烃基。R7为氢原子或含1至5个碳原子的饱和烃基。另外,这些芳基烷氧基硅烷和芳基硅氮烷的混合物也可以使用。
具有代表性的芳基烷氧基硅烷和芳基硅氮烷单体包括:苯基三乙氧基硅烷、三(二甲氨基)苯基硅烷、双(二甲氨基)二苯基硅烷和双(二甲氨基)甲苯基硅烷。
特别好的芳基烷氧基硅烷和芳基硅氮烷单体包括那些R4为未取代或取代的苯基、R6为含1至4个碳原子的饱和烃基或R7为氢原子或含1至4个碳原子的饱和烃基的单体。芳烷氧基硅烷单体是最好的,如苯基三烷氧基硅烷(如苯基三乙氧基硅烷)。
任何能溶解氨烷氧基硅烷和芳烷氧基硅烷或芳基硅氮烷并可与水混溶的合适的溶剂都可以使用。典型的溶剂包括本领域技术人员熟知的,例如,醇类如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、异戊醇等;醚类如溶纤剂(如甲基溶纤剂)、二甘醇二甲醚、二噁烷、丁基二甘醇一乙醚、四氢呋喃等;芳香族醇如苯酚等;多羟基醇如乙二醇、四亚甲基二醇等;酮类如甲乙酮、甲基异丁基酮,二乙酮等;等以及它们的混合物。较好的溶剂包括甲醇、乙醇和异丙醇。
以芳烷氧基硅烷单体与氨烷氧基硅烷单体的摩尔比为约1∶3至约4∶1进行反应较好,更好的是从约2∶3至约2.5∶1,水与单体总量的摩尔比从约0.5∶1至约2∶1较好,更好地是从约0.9∶1至约1.7∶1。
在制备该有机溶液时,可加入其它单体。例如,为了改进膜的均匀度,可使用有利于交联的高官能度的硅烷单体,如四官能度的硅烷单体。在本发明较好的技术方案中,除了氨烷氧基硅烷和芳烷氧基硅烷或芳基硅氮烷单体和水外,还加入四烷氧基硅烷单体(如四乙氧基硅烷)一起反应以制备有机溶液。以单体总摩尔数为基准,所用的四烷氧基硅烷单体的比例不超过约50%为宜,不超过约45%更好,约20%至约45%最好。
关于所用的有机溶液及其制备的其它细节,可参考1990年3月15日提出的正在审查中的美国专利申请第494,006号,该申请的全部内容在此并入本说明书作为公开内容的一部分。
然后在足以使溶剂挥发并形成部分固化涂层的温度下加热涂敷表面。此时不必使膜完全固化,事实上,只需使膜固化到具有一定完整性足以使下一步涂敷溶液得以进行即可。一般说来,温度通常为约85℃至约150℃,从约90℃至约110℃较好;加热时间从约0.5分至约20分钟,从约5分至约10分钟较好。然而部分固化的实际条件可在很宽范围内变化,这取决于多种因素,如有机溶液中所用的特定单体,以及它们的摩尔比等等,这些对于本领域技术人员是显而易见的。
然后,采用任一适用的方法将含有聚酰亚胺前体物质的溶液涂到部分固化层上。合适的聚酰亚胺前体物质包括由芳香族二酐与二胺(芳香族二胺更好)缩聚而成的聚酰胺酸聚合物和相应的聚酰胺酯聚合物。合适的芳香族二酐包括1,2,4,5-苯四酸二酐、2,2-双(3,4-二羧苯基)丙烷二酐、2,3,6,7-萘四羧酸二酐、2,2′,3,3′-二苯基四羧基二酐和二苯酮四羧基二酐。合适的二胺包括间苯二胺、对苯二胺和4,4′-二氨基苯醚。适用于本发明目的并可作为例证的聚酰亚胺前体物质和它们制备的方法公布在美国专利第3,179,614号,第3,264,250和第4,612,210号中,它们的全部公开内容在此并入本文作为本说明书公开内容的一部分。特别适用的聚酰胺酸聚合物可从特拉华州Wilmington的E、I、dupout deNemours公司买到,其商品名是“PI-5810D”、“PI2545”和“PI2525”。
典型的方法是将聚酰亚胺前体溶解在合适的惰性溶剂中,然后用旋转涂敷的方式将溶液涂到部分固化层上,旋转速度取决于所希望的厚度,约为1,000-7,000转/分。对于溶剂没有过分的限制,许多溶剂或溶剂的混合物都可使用,例如,N-甲基吡咯烷酮(NMP)、二甲基乙酰胺(DMAC)、二甲基甲酰胺(DMF)、二甲基亚砜(DMSO)或这些溶剂与各种普通烃溶剂的合适的混合物。
涂敷溶液以后,将表面加热以使部分固化层和聚酰亚胺前体物质同时固化。在此步骤过程中,部分固化层发生固化形成硅倍半环氧乙烷共聚物,而聚酰亚胺前体物质则转化成相应的聚酰亚胺。实际上温度、压力和时间等固化条件可在很宽范围内变化,通常这取决于有机溶液中所用的单体和它们的摩尔比、所用的聚酰亚胺前体物质、生成的固化层的希望厚度,以及对于本领域技术熟练人员来说应是显而易见的其它因素。然而通常情况下典型的条件为在大气压下、温度高于约200℃,保持约15至60分钟。
在较好的技术方案中,在大气压下的热处理是以一条列步骤进行的。在这种方式中,衬底暴露在约85℃至160℃温度下,或在此范围内顺序连续升温以除去溶剂,然后暴露于超过约350℃的高温下以形成最终的固化层。
显然,在固化过程中,共聚物通过氨基与底层金属配位结合,同时它还进一步起钝化金属表面的作用。另外,共聚物似乎进一步与聚酰亚胺前体反应形成胺盐(它以通常方式酰亚胺化),通过氨基形成共价联接。无论如何,固化的硅倍半环氧乙烷共聚物膜层在聚酰亚胺膜与金属表面之间产生很强的键合,既是防湿的又是抗氧化的。另外,已经发现它比常用的粘合促进剂呈现增强的热稳定性特征,同时还提供所希望的电学特性,如低介电常数。另一个操作处理方面的优点是不需要单独的完全固化步骤就可形成促进粘合层。
下面的实施例用来说明本发明。
制备有机溶液
对比实例A
将490毫升干燥甲醇(含水少于0.01%)的等分试样转入干净干燥的Nalgene(聚乙烯)瓶中。将10毫升高纯度市售Unian Carbide公司出产的产品名为“Alloo”的3-氨丙基三乙氧基硅烷的等分试样加到甲醇中,充分混合溶液并用放在适当位置的瓶盖来控制暴露于空气的程度(上面说的高纯度是指用气相色谱测定的单体含量高于99.5%、离子总浓度小于5ppm)。一边摇动硅烷/甲醇溶液,一边加入1毫升去离子蒸馏水,然后盖上瓶盖,剧烈振摇混合物10秒至20秒。将密闭的容器置于转动机(roller mill)上使溶液在室温下混合约16小时。在确保空气曝露小的条件下用0.2微米的聚丙烯过滤器过滤老化的溶液。
实施例1.
将490毫升干燥甲醇(含水少于0.01%)的等分试样转入干净、干燥的Nalgene(聚乙烯)瓶中。将5毫升高纯度市售Petrarch Systems有限公司出产的商品名为“PO320”的苯基三乙氧基硅烷的等分试样加到甲醇中。充分混合溶液并用放在适当位置的瓶盖来控制暴露于空气的程度(高纯度的含义同对比实例A)。一边摇动硅烷/甲醇溶液,一边加入1毫升去离子蒸馏水,然后盖上瓶盖,剧烈振摇混合物10秒至20秒。溶液中放有磁搅拌棒,将瓶子置于磁搅拌器上。这时,将5毫升高纯度的(含义同对比实例A)市售Union Carbide公司出产品名为“A1100”的3-氨丙基三乙氧基硅烷置于聚丙烯加料漏斗中,并与上述瓶子相连;然后在充分搅拌下在1小时中将其加入瓶中。添加完毕后,将瓶子置于转动机上混合约16小时。在确保空气曝露最小的条件下用0.2微米聚丙烯过滤器过滤老化的溶液。
对比实施例B
将490毫升干燥甲醇(含水少于0.01%)的等分试样转入干净、干燥的Nalgene(聚丙烯)瓶中。将10毫升高纯度(含义与对比实例A相同)市售Dow Corning公司的品名为“Z6020”的N-β-氨乙基-γ-氨丙基三甲氧基硅烷的等分试样加到甲醇中,充分混合溶液并用放于适当位置的瓶盖来控制暴露于空气的程度。一边摇振硅烷/甲醇溶液,一边加入一毫升去离子蒸馏水,然后盖上瓶盖,剧烈振动混合物10秒至20秒。将密闭的容器置于转动机上使溶液在室温下混合约16小时。在确保空气曝露最小的条件下用0.2微米聚丙烯过滤器过滤老化的溶液。
实施例2
将490毫升干燥甲醇(含水少于0.01%)的等分试样转入干净、干燥的Nalgene(聚乙烯)瓶中。将5毫升高钝度(含义同时比实例A)市售Petrarch Systems有限公司的品名为“PO320”的苯基三乙氧基硅烷的等分试样加到甲醇中,充分混合溶液并用放于适当位置的瓶盖来控制暴露于空气的程度。一边摇振硅烷/甲醇溶液,一边加入一毫升去离子水,然后盖上瓶子,剧烈振动混合物10秒至20秒。溶液中放有磁搅拌棒,将瓶子置于磁搅拌器上。此时,将5毫升高钝度(含义同时比实例A)市售Dow Corning公司的品名为“Z6020”的N-β-氨乙基-γ-氨丙基三甲氧基硅烷置于聚丙烯加料漏斗中并与上述瓶子相连,在良好搅拌条件下在1小时中将其加入瓶中。添加完毕后,将瓶子置于转动机上使溶液混合约16小时。在确保空气暴露最小的条件下,用0.2微米聚丙烯过滤器过滤老化的溶液。
实施例3
将385毫升干燥甲醇(含水少于0.01%)的等分试样转入干净、干燥的Nalgene(聚乙烯)瓶中。将5毫升高纯度(含义同对比实例A)市售Petrarch Syslems有限公司的品名为“PO320”的苯基三乙氧基硅烷的等分试样加到甲醇中,充分混合溶液并用放于适当位置的瓶盖来控制暴露于空气的程度。一边摇振硅烷/甲醇溶液,一边慢慢加入1.25毫升去离子水,然后盖上瓶子,剧烈摇动混合物10秒至20秒。溶液中放有磁搅拌棒,将瓶子置于磁搅拌器上。此时,将2.4毫升高纯度(含义同时对比实例A)市售Union Carbide公司的品名为“A1100”的3-氨丙基三乙氧基硅烷与100毫升干燥甲醇一起置于聚丙烯加料漏斗中,并与上述瓶子相连,在良好的搅拌条件下,在1小时中将溶液加入瓶中。然后在良好的搅拌条件下,在几分钟内加入4.6毫升市售Petrarch Systems有限公司出品的四乙氧基硅烷(TEOS)。添加完毕后,将瓶子置于转动机上,使溶液混合约16小时。在确保空气暴露最少的条件下,用0.2微米聚丙烯过滤器过滤老化的溶液。
形成固化的结构
对比实例C、D和实施例4-6
将上面制得的有机溶液涂在硅衬底圆片上。这些圆片是采用在表面上蒸镀一层钛(5,000埃),再蒸镀上一层铜(10,000埃)的方法制备的。然后将涂敷的片材在400℃的定形气(10%氢气/90%氮气)中退火30分钟。将有机溶液涂到镀铜的片材上,静置15秒,然后使片材在3,000转/分的速度下旋转30秒钟。随后在100℃温度下加热衬底10分钟以除去过量的甲醇,并在衬底上形成部分固化膜。
在此之后,将溶于NMP的聚酰胺酸(由市售E、I。dupontdeNemours公司的品名为“PI-5810D”的双苯四羧酸二酐和对苯二胺制得,固体含量为11%)溶液旋转涂敷在部分固化膜上,在初始旋转速度为500转/分下进行15秒钟,接着以最终旋转速度为4,000转/分进行30秒。然后,在常压下在空气中使用8位热盘烘烤片材,分别在温度为95℃/105℃/105℃/115℃/115℃/135℃/135℃/135℃下各烘烤2.5分钟。烘烤之后,在流动的干燥氮气中,400℃温度下,在烘箱中对片材进行最后的固化共45分钟,氮气已被过滤过以除去直径大于0.2微米的颗粒,并控制氧气含量小于10ppm以保持衬底的氧化为最小。
上述方法可得到固化结构,其硅倍半环氧乙烷薄膜的厚度接近200埃,聚酰亚胺薄膜的厚度接近10,000埃。
对固化的结构进行检测,结果列于表Ⅰ。在剥离试验中,在片材背面划线作标记。然后将片材劈开,使固化的聚酰亚胺膜保持完整。将片材弯成90°角,这时聚酰亚胺膜相当于一个折叶,这样就能观察粘合特性。更详细的描述参见Rothman,L、B、的“聚酰亚胺薄膜的特性”,电化学协会杂志;固态科学和技术,第127卷,第10期(198年10月)2216-2220页,其全部内容在此并入本文作为本说明书公开内容的一部分。将片材暴露于水汽中后(85℃/80%相对温度下14天)进行检测。检测采用下面的标准:当聚酰亚胺薄膜在整个宽度上从硅倍半环氧乙烷共聚物表面脱离时为全剥离;当聚酰亚胺薄膜在整个宽度上没有从硅倍半环氧乙烷共聚物表面完全脱离时为部分剥离;当聚酰亚胺膜完全没有从硅倍半环氧乙烷共聚物表面脱离时为无剥离。
采用对每一个固化结构测定铜表面反射系数的方法测定耐腐蚀性,使用的仪器是带有反射度测量附件的Hitachi紫外可见光谱仪,用800毫微米处的吸光度进行测量,用铝镜作基准调节仪器零点。使用下列数字标度:铜,0.05-0.1;氧化的铜,0.66。实施例4-6的结构显示出低吸光值,证明硅倍半环氧乙烷聚合物层对底层铜有良好的防腐蚀作用。
Claims (28)
1、改进聚酰亚胺涂层与金属表面粘合的方法,其特征在于由下列步骤组成:
(a)将有机溶液涂到所述的金属表面上,该溶液是由氨烷氧基硅烷单体、芳烷氧基硅烷或芳基硅氮烷单体和水在溶剂中反应制得的;
(b)在使所述表面上能形成部分固化膜的条件下加热所述表面;
(c)将含有聚酰亚胺前体物质的溶液涂到所述部分固化膜上;和
(d)在能同时形成固化硅倍半环氧乙烷共聚物膜和聚酰亚胺膜的条件下加热所述表面。
2、根据权利要求1的方法,其特征在于所述的氨烷氧基硅烷单体是下式表示的氨基三烷氧基硅烷或其混合物:
其中:
R1为氢原子;具有1-5个碳原子的饱和烃基或氨基取代的饱和烃基;或烷基取代的苯基或其衍生物,其中烷基含有1-5个碳原子;
R2为含有2-6个碳原子的饱和烃基或烷基取代的苯基,其中每一个烷基含有1-5个碳原子;和
R3为含有1-8个碳原子的饱和烃基;
所述芳烷氧基硅烷或芳基硅氮烷单体用下式表示:
其中,R4为未取代或取代的芳香族基团,Y为(OR6)或N(R7)2,其中R6为含有1-5个碳原子的饱和烃基,R7为氢原子或含有1-5个碳原子的饱和烃基。
3、根据权利要求2的方法,其特征在于进行所述反应所用的芳烷氧基硅烷单体与氨烷氧基硅烷单体的摩尔比为约1∶3至约4∶1,水与单体总量的摩尔比为约0.5∶1至约2∶1。
4、根据权利要求3的方法,其特征在于进行所述反应所用的芳烷氧基硅烷单体与氨烷氧基硅烷单体的摩尔比从约2∶3至约2.5∶1,水与单体总量的摩尔比从约0.9∶1至约1.7∶1。
5、根据权利要求2的方法,其特征在于所述的有机溶液是先将所述芳烷氧基硅烷或芳基硅氮烷单体溶解在所述溶剂中,加入水,然后加入所述的氨烷氧基硅烷单体而制备的;
所述的溶剂选自甲醇、乙醇和异丙醇;
所述的溶液在被涂到所述衬底之前,先进行至少约2小时的老化。
6、根据权利要求2的方法,其特征在于所述的有机溶液是由氨烷氧基硅烷单体、芳烷氧基硅烷或芳基硅氮烷单体、四烷氧基硅烷单体和水在溶剂中反应制备的。
7、根据权利要求6的方法,其特征在于所述的四烷氧基硅烷单体是四乙氧基硅烷,以单体总摩尔数为基准,其用量比例为约20%至约45%。
9、根据权利要求8的方法,其特征在于所述的氨基三烷氧基硅烷选自γ-氨丙基三甲氧基硅烷、γ-氨丙基三乙氧基硅烷、N-β-(氨乙基)-γ-氨丙基三甲氧基硅烷和N-β-(氨乙基)-γ-氨丙基三乙氧基硅烷,所述的芳烷氧基硅烷单体是苯基三乙氧基硅烷。
10、根据权利要求1的方法,其特征在于在约85℃至约150℃的温度下加热所述表面约0.5分至约20分钟,以形成所述的部分固化膜。
11、根据权利要求10的方法,其特征在于在约90℃至约110℃的温度下加热所述表面约5分至约10分钟,以形成所述的部分固化膜。
12、根据权利要求1的方法,其特征在于将含有双苯二酐一对苯二胺聚酰胺酸或其酯的溶液涂到所述的部分固化膜上。
13、根据权利要求1的方法,其特征在于将含有1,2,4,5-苯四二酸酐-氧双苯胺聚酰胺酸或其酯的溶液涂到所述的部分固化膜上。
14、根据权利要求1的方法,其特征在于在高于约200℃的温度下进行所述的同时固化步骤。
15、根据权利要求14的方法,其特征在于在高于约350℃的温度下进行所述的同时固化步骤。
16、根据权利要求1的方法,其特征在于所述的金属选自铜、铝、银、铬、铅、锡、金、钛和钨。
17、改进聚酰亚胺膜对带有金属镀敷图案的半导体基底的粘合力的方法,其特征在于由下列步骤组成:
(a)将有机溶液涂到衬底上,该溶液是由氨烷氧基硅烷单体、芳烷氧基硅烷或芳基硅氮烷单体和水在溶剂中反应而制备的,其中所述的氨烷氧基硅烷单体是由下式表示的物质或它的混合物:
其中:
R1为氢原子或含2或3个碳原子的饱和烃基或氨基取代的饱和烃基;
R2为含3-6个碳原子的饱和烃基;
R3为含1-4个碳原子的饱和烃基;
所述的芳烷氧基硅烷或芳基硅氮烷单体是由下式表示的:
其中,R4为未取代或取代的苯基,Y为OR6或N(R7)2,其中R6为含1-4个碳原子的饱和烃基,R7为氢原子或含1-4个碳原子的饱和烃基;
进行所述的反应所用的芳烷氧基硅烷单体与氨烷氧基硅烷单体的摩尔比从约1∶3至约4∶1,水与单体总量的摩尔比从约0.5∶1至约2∶1;在
在约85℃至约150℃的温度下加热所述衬底约0.5分至约20分钟,以形成所述的部分固化膜;
将含有聚酰亚胺前体物质的溶液涂到所述的部分固化膜上;
在高于200℃的温度下加热所述衬底以形成固化的硅倍半环氧乙烷共聚物膜和聚酰亚胺膜。
18、根据权利要求17的方法,其特征在于所述氨基三烷氧基硅烷单体选自γ-氨丙基三甲氧基硅烷、γ-氨丙基三乙氧基硅烷、N-β-氨乙基-γ-氨丙基三甲氧基硅烷和N-β-氨乙基-γ-氨丙基三乙氧基硅烷,所述芳烷氧基硅烷单体是苯基三乙氧基硅烷。
19、根据权利要求18的方法,其特征在于在约90℃至约110℃的温度下加热所述衬底约5分至10分钟,以形成所述的部分固化膜;在高于约350℃的温度下进行所述的同时固化步骤。
20、根据权利要求19的方法,其特征在于由氨烷氧基硅烷单体、芳烷氧基硅烷或芳基硅氮烷单体、四烷氧基硅烷单体和水在溶剂中反应制备所述有机溶液。
21、根据权利要求20的方法,其特征在于所述四烷氧基硅烷单体是四乙氧基硅烷,以单体总摩尔数为基准,其用量比例为约20%至约45%。
22、固化的复合结构,其特征在于包含金属、聚酰亚胺膜、和介于所述金属与所述的聚酰亚胺膜中间的硅倍半环氧乙烷共聚物膜,所述的共聚物用于改进所述聚酰亚胺膜对所述金属的粘合力,所述结构是根据权利要求1的方法得到的。
23、固化的复合结构,其特征在于包含金属、聚酰亚胺膜、和介于所述金属与所述的聚酰亚胺膜中间的硅倍半环氧乙烷共聚物膜,所述的共聚物用于改进所述聚酰亚胺膜对所述金属的粘合力,所述结构是根据权利要求8的方法得到的。
24、固化的复合结构,其特征在于包含金属、聚酰亚胺膜、和介于所述金属与所述聚酰亚胺膜中间的硅倍半环氧乙烷共聚物膜、所述的共聚物用于改进所述聚酰亚胺膜对所述金属的粘合力,所述结构是根据权利要求9的方法得到的。
25、半导体结构,其特征在于包含带有有金属镀敷图案的衬底、聚酰亚胺膜、和介于所述衬底与所述聚酰亚胺膜中间的硅倍半环氧乙烷共聚物膜,所述的共聚物用于改进所述聚酰亚胺膜对所述金属的粘合力,所述结构是根据权利要求17的方法得到的。
26、半导体结构,其特征在于包含带有金属镀敷图案的衬底、聚酰亚胺膜、和介于所述衬底与所述聚酰亚胺膜中间的硅倍半环氧乙烷共聚物膜,所述的共聚物用于改进所述聚酰亚胺膜对所述金属的粘合力,所述结构是根据权利要求19的方法得到的。
27、固化的复合结构,其特征在于包含金属、聚酰亚胺膜、和介于所述金属和所述聚酰亚胺膜中间的硅倍半环氧乙烷共聚物膜,所述共聚物用以改进所述聚酰亚胺膜对所述金属的粘合力。
28、半导体结构,其特征在于包含带有金属镀敷图案的衬底、聚酰亚胺膜、和介于所述衬底与所述聚酰亚胺膜之间的硅倍半环氧乙烷膜,所述共聚物用以改进所述聚酰亚胺膜对所述金属的粘合力。
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US07/604,702 | 1990-10-26 | ||
US07/604,702 US5114757A (en) | 1990-10-26 | 1990-10-26 | Enhancement of polyimide adhesion on reactive metals |
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EP (1) | EP0487857B1 (zh) |
JP (1) | JPH0757814B2 (zh) |
KR (1) | KR950000709B1 (zh) |
CN (2) | CN1051169C (zh) |
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Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5194928A (en) * | 1991-01-14 | 1993-03-16 | International Business Machines Corporation | Passivation of metal in metal/polyimide structure |
US5397741A (en) * | 1993-03-29 | 1995-03-14 | International Business Machines Corporation | Process for metallized vias in polyimide |
JP3395269B2 (ja) * | 1993-07-16 | 2003-04-07 | チッソ株式会社 | 低熱伝導率ポリイミドシロキサンフィルム |
US5474956A (en) * | 1995-03-14 | 1995-12-12 | Hughes Aircraft Company | Method of fabricating metallized substrates using an organic etch block layer |
US5614324A (en) * | 1995-07-24 | 1997-03-25 | Gould Electronics Inc. | Multi-layer structures containing a silane adhesion promoting layer |
US5760480A (en) * | 1995-09-20 | 1998-06-02 | Advanced Micro Devics, Inc. | Low RC interconnection |
US6303278B1 (en) | 1997-01-31 | 2001-10-16 | Cuptronic Ab | Method of applying metal layers in distinct patterns |
SE508280C2 (sv) * | 1997-01-31 | 1998-09-21 | Cuptronic Ab | Förfarande för att öka vidhäftningsförmågan hos ledande material till ytskikt av polymermaterial |
US6121159A (en) * | 1997-06-19 | 2000-09-19 | Lsi Logic Corporation | Polymeric dielectric layers having low dielectric constants and improved adhesion to metal lines |
US6303525B1 (en) * | 2000-08-18 | 2001-10-16 | Philips Electronics No. America Corp. | Method and structure for adhering MSQ material to liner oxide |
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ATE434082T1 (de) * | 2006-04-10 | 2009-07-15 | Linea Tergi Ltd | Verfahren zur applizierung eines metalls auf ein substrat |
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JP6784671B2 (ja) | 2014-11-26 | 2020-11-11 | コーニング インコーポレイテッド | 強化および耐久性ガラス容器の製造方法 |
JP6479463B2 (ja) * | 2014-12-26 | 2019-03-06 | 日鉄ケミカル&マテリアル株式会社 | ポリイミドフィルム積層体 |
WO2016173600A1 (en) * | 2015-04-30 | 2016-11-03 | Coloplast A/S | Adhesive composition |
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BR112018008744B1 (pt) | 2015-10-30 | 2022-09-06 | Corning Incorporated | Artigos de vidro com revestimento de óxido metálico e polímero misto |
CN110859029B (zh) * | 2018-08-23 | 2022-04-01 | 鹏鼎控股(深圳)股份有限公司 | 柔性电路板及该柔性电路板制作方法 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US494006A (en) * | 1893-03-21 | Shutter-worker | ||
US473978A (en) * | 1892-05-03 | Hame-tug clip | ||
US3179614A (en) * | 1961-03-13 | 1965-04-20 | Du Pont | Polyamide-acids, compositions thereof, and process for their preparation |
US3264250A (en) * | 1963-12-18 | 1966-08-02 | Du Pont | Copolymeric polyamide-acids and polyimides |
US3520683A (en) * | 1967-05-19 | 1970-07-14 | Bell Telephone Labor Inc | Photoresist method and products produced thereby |
US3684592A (en) * | 1969-09-30 | 1972-08-15 | Westinghouse Electric Corp | Passivated surfaces and protective coatings for semiconductor devices and processes for producing the same |
US4103045A (en) * | 1972-07-31 | 1978-07-25 | Rhone-Poulenc, S.A. | Process for improving the adhesion of coatings made of photoresistant polymers to surfaces of inorganic oxides |
US4030948A (en) * | 1975-07-21 | 1977-06-21 | Abe Berger | Polyimide containing silicones as protective coating on semiconductor device |
DE3278567D1 (en) * | 1981-10-03 | 1988-07-07 | Japan Synthetic Rubber Co Ltd | Solvent-soluble organopolysilsesquioxanes, processes for producing the same, and compositions and semiconductor devices using the same |
NL8203980A (nl) * | 1982-10-15 | 1984-05-01 | Philips Nv | Werkwijze voor de fotolithografische behandeling van een substraat. |
US4590258A (en) * | 1983-12-30 | 1986-05-20 | International Business Machines Corporation | Polyamic acid copolymer system for improved semiconductor manufacturing |
US4758476A (en) * | 1984-12-12 | 1988-07-19 | Hitachi Chemical Company, Ltd. | Polyimide precursor resin composition and semiconductor device using the same |
US4612210A (en) * | 1985-07-25 | 1986-09-16 | International Business Machines Corporation | Process for planarizing a substrate |
US4786569A (en) * | 1985-09-04 | 1988-11-22 | Ciba-Geigy Corporation | Adhesively bonded photostructurable polyimide film |
US4723978A (en) * | 1985-10-31 | 1988-02-09 | International Business Machines Corporation | Method for a plasma-treated polysiloxane coating |
JPH0791509B2 (ja) * | 1985-12-17 | 1995-10-04 | 住友化学工業株式会社 | 半導体用絶縁膜形成塗布液 |
US4782009A (en) * | 1987-04-03 | 1988-11-01 | General Electric Company | Method of coating and imaging photopatternable silicone polyamic acid |
-
1990
- 1990-10-26 US US07/604,702 patent/US5114757A/en not_active Expired - Fee Related
-
1991
- 1991-07-03 JP JP3162836A patent/JPH0757814B2/ja not_active Expired - Fee Related
- 1991-09-11 CA CA002051174A patent/CA2051174C/en not_active Expired - Fee Related
- 1991-09-27 EP EP91116498A patent/EP0487857B1/en not_active Expired - Lifetime
- 1991-09-27 DE DE69118119T patent/DE69118119T2/de not_active Expired - Fee Related
- 1991-09-30 KR KR1019910017070A patent/KR950000709B1/ko not_active IP Right Cessation
- 1991-10-12 CN CN91109639A patent/CN1051169C/zh not_active Expired - Fee Related
-
1992
- 1992-03-21 TW TW081102146A patent/TW273566B/zh active
-
1998
- 1998-11-06 CN CN98123868A patent/CN1087761C/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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EP0487857A3 (en) | 1992-10-07 |
CN1051169C (zh) | 2000-04-05 |
TW273566B (zh) | 1996-04-01 |
CN1231319A (zh) | 1999-10-13 |
CN1087761C (zh) | 2002-07-17 |
CA2051174A1 (en) | 1992-04-27 |
EP0487857B1 (en) | 1996-03-20 |
JPH05222193A (ja) | 1993-08-31 |
KR920008165A (ko) | 1992-05-27 |
CA2051174C (en) | 1994-05-31 |
DE69118119T2 (de) | 1996-10-02 |
US5114757A (en) | 1992-05-19 |
EP0487857A2 (en) | 1992-06-03 |
DE69118119D1 (de) | 1996-04-25 |
KR950000709B1 (ko) | 1995-01-27 |
JPH0757814B2 (ja) | 1995-06-21 |
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