KR20040103659A - 실록산계 수지 및 이를 이용한 반도체 층간 절연막 - Google Patents
실록산계 수지 및 이를 이용한 반도체 층간 절연막 Download PDFInfo
- Publication number
- KR20040103659A KR20040103659A KR1020030035276A KR20030035276A KR20040103659A KR 20040103659 A KR20040103659 A KR 20040103659A KR 1020030035276 A KR1020030035276 A KR 1020030035276A KR 20030035276 A KR20030035276 A KR 20030035276A KR 20040103659 A KR20040103659 A KR 20040103659A
- Authority
- KR
- South Korea
- Prior art keywords
- siloxane
- solvent
- formula
- insulating film
- interlayer insulating
- Prior art date
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 229920005989 resin Polymers 0.000 title claims abstract description 56
- 239000011347 resin Substances 0.000 title claims abstract description 56
- 239000011229 interlayer Substances 0.000 title claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 239000004065 semiconductor Substances 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000524 functional group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- 229920001610 polycaprolactone Polymers 0.000 claims description 3
- 239000004632 polycaprolactone Substances 0.000 claims description 3
- -1 potassium hydroxide Siloxane Chemical class 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000001029 thermal curing Methods 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 2
- 229920001353 Dextrin Polymers 0.000 claims 1
- 239000004375 Dextrin Substances 0.000 claims 1
- 235000019425 dextrin Nutrition 0.000 claims 1
- 230000000704 physical effect Effects 0.000 abstract description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 3
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 239000010409 thin film Substances 0.000 description 27
- 239000010408 film Substances 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 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 3
- DMEXFOUCEOWRGD-UHFFFAOYSA-N chloro-[chloro(dimethyl)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(Cl)O[Si](C)(C)Cl DMEXFOUCEOWRGD-UHFFFAOYSA-N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 229920000642 polymer Polymers 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
- 239000000523 sample Substances 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 239000001116 FEMA 4028 Substances 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
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000007373 indentation Methods 0.000 description 2
- 239000005453 ketone based solvent 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011827 silicon-based solvent Substances 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
- VGHSPBIUALACLV-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[Si]1(O[Si](O[Si](O[Si](O1)(C=C)C)(C=C)C)(C=C)C)C=C.C[Si]1(O[Si](O[Si](O[Si](O1)(C=C)C)(C=C)C)(C=C)C)C=C VGHSPBIUALACLV-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
- WNPBAIOAPGZVHO-UHFFFAOYSA-N Cl[Si](O[Si](O[Si](O[Si](Cl)(C)C)(C)C)(C)C)(C)C.Cl[Si](O[Si](O[Si](O[Si](Cl)(C)C)(C)C)(C)C)(C)C Chemical compound Cl[Si](O[Si](O[Si](O[Si](Cl)(C)C)(C)C)(C)C)(C)C.Cl[Si](O[Si](O[Si](O[Si](Cl)(C)C)(C)C)(C)C)(C)C WNPBAIOAPGZVHO-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 238000004458 analytical method Methods 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
- MVIOINXPSFUJEN-UHFFFAOYSA-N benzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=CC=C1 MVIOINXPSFUJEN-UHFFFAOYSA-N 0.000 description 1
- GJIYNWRLGOMDEX-UHFFFAOYSA-N bis[[chloro(dimethyl)silyl]oxy]-dimethylsilane Chemical compound C[Si](C)(Cl)O[Si](C)(C)O[Si](C)(C)Cl GJIYNWRLGOMDEX-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920003209 poly(hydridosilsesquioxane) Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
-
- 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
- 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
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
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- H01L21/02107—Forming insulating materials on a substrate
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- 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
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Abstract
Description
실록산수지 | 모노머 종류 (mmol) | HCl(mmol) | H2O(mmol) | 얻은 수지량(g) | ||||
모노머(A) | 모노머B) | 모노머(C) | 모노머(D) | 모노머(E) | ||||
(a) | 6.621 | 15.450 | 0.110 | 310 | 4.85 | |||
(b) | 15.450 | 15.450 | 0.216 | 721 | 9.70 | |||
(c) | 11.998 | 5.142 | 0.145 | 514 | 6.85 | |||
(d) | 11.998 | 5.142 | 0.145 | 514 | 6.70 | |||
(e) | 11.998 | 5.142 | 0.145 | 514 | 7.55 | |||
(f) | 11.998 | 5.142 | 0.145 | 857 | 7.60 | |||
(g) | 11.998 | 5.142 | 1.450 | 514 | 7.85 | |||
(h) | 11.998 | 5.142 | 0.101 | 514 | 7.80 | |||
(i) | 11.998 | 5.142 | 0.080 | 514 | 7.10 | |||
(j) | 11.998 | 5.142 | 0.048 | 514 | 6.35 | |||
(k) | 9.599 | 22.397 | 0.102 | 627 | 7.53 | |||
(l) | 7.199 | 28.796 | 0.101 | 617 | 7.56 | |||
(m) | 4.799 | 43.194 | 0.115 | 705 | 7.71 |
실록산 수지 | Si-OH(%) | Si-OCH3(%) | Si-CH3(%) |
(a) | 6.2 | 0.3 | 93.5 |
(b) | 14.3 | 0.5 | 85.1 |
(c) | 28.6 | 0.7 | 70.7 |
(d) | 30.6 | 1.0 | 68.4 |
(e) | 28.1 | 0.9 | 71.0 |
(f) | 29.9 | 0.6 | 69.5 |
(g) | 18.3 | 0.7 | 81.0 |
(h) | 32.4 | 0.9 | 66.7 |
(i) | 33.3 | 1.0 | 65.7 |
(j) | 41.2 | 1.4 | 57.4 |
(k) | 33.2 | 1.8 | 65.0 |
(l) | 32.1 | 1.5 | 66.4 |
(m) | 27.3 | 1.5 | 71.2 |
박막 조성물 | 두께(Å) | 굴절율 | 굴절율 균일도(%) | 두께 균일도(%) | ||
실록산 수지종류 | 실록산수지의 함량(중량%) | 기공형성물질의 함량(중량%) | ||||
(a) | 100 | - | 9647 | 1.4056 | 0.074 | 2.09 |
(a) | 70 | 30 | 8946 | 1.3614 | 0.158 | 1.53 |
(b) | 100 | - | 11665 | 1.4204 | 0.049 | 0.45 |
(b) | 70 | 30 | 9283 | 1.3412 | 0.037 | 1.99 |
(c) | 100 | - | 10193 | 1.4299 | 0.031 | 0.62 |
(c) | 70 | 30 | 8983 | 1.3298 | 0.105 | 1.81 |
(d) | 100 | - | 11131 | 1.4355 | 0.010 | 0.45 |
(d) | 70 | 30 | 10075 | 1.3278 | 0.196 | 1.10 |
(e) | 100 | - | 10289 | 1.4395 | 0.052 | 2.56 |
(e) | 70 | 30 | 9604 | 1.3202 | 0.216 | 2.34 |
(f) | 100 | - | 12051 | 1.4358 | 0.081 | 1.23 |
(f) | 70 | 30 | 7540 | 1.3290 | 0.107 | 1.57 |
(g) | 100 | - | 13453 | 1.4207 | 0.047 | 0.92 |
(g) | 70 | 30 | 8829 | 1.3385 | 0.089 | 1.04 |
(h) | 100 | - | 12011 | 1.4397 | 0.023 | 1.38 |
(h) | 70 | 30 | 9739 | 1.3225 | 0.059 | 1.97 |
(i) | 100 | - | 11513 | 1.4403 | 0.072 | 2.52 |
(i) | 70 | 30 | 8508 | 1.3217 | 0.126 | 1.48 |
(j) | 100 | - | 12485 | 1.4454 | 0.032 | 0.72 |
(j) | 70 | 30 | 9787 | 1.3170 | 0.089 | 0.91 |
(k) | 100 | - | 10138 | 1.4249 | 0.081 | 1.31 |
(k) | 70 | 30 | 9387 | 1.3128 | 0.031 | 1.02 |
(l) | 100 | - | 7681 | 1.4190 | 0.076 | 1.30 |
(l) | 70 | 30 | 7499 | 1.3065 | 0.030 | 0.94 |
(m) | 100 | - | 8245 | 1.4086 | 0.082 | 1.05 |
(m) | 70 | 30 | 7958 | 1.3206 | 0.028 | 0.75 |
박막 조성물 | 유전율 | ||
실록산 수지종류 | 실록산 수지 함량(중량%) | 기공형성 물질 함량(중량%) | |
(a) | 100 | - | 2.83 |
(a) | 70 | 30 | 2.67 |
(b) | 100 | - | 2.72 |
(b) | 70 | 30 | 2.23 |
(c) | 100 | - | 2.74 |
(c) | 70 | 30 | 2.37 |
(d) | 100 | - | 2.79 |
(d) | 70 | 30 | 2.25 |
(e) | 100 | - | 2.71 |
(e) | 70 | 30 | 2.17 |
(f) | 100 | - | 2.78 |
(f) | 70 | 30 | 2.19 |
(g) | 100 | - | 2.80 |
(g) | 70 | 30 | 2.28 |
(h) | 100 | - | 2.80 |
(h) | 70 | 30 | 2.21 |
(i) | 100 | - | 2.81 |
(i) | 70 | 30 | 2.20 |
(j) | 100 | - | 2.66 |
(j) | 70 | 30 | 2.10 |
(k) | 100 | - | 2.76 |
(k) | 70 | 30 | 2.26 |
(l) | 100 | - | 2.75 |
(l) | 70 | 30 | 2.26 |
(m) | 100 | - | 2.71 |
(m) | 70 | 30 | 2.20 |
박막 조성물 | 경도(GPa) | 모듈러스(GPa) | ||
실록산 수지 종류 | 실록산 수지 함량(중량%) | 기공형성 물질 함량(중량%) | ||
(a) | 100 | - | 0.40 | 2.47 |
(a) | 70 | 30 | 0.27 | 2.06 |
(b) | 100 | - | 0.59 | 3.62 |
(b) | 70 | 30 | 0.39 | 2.46 |
(c) | 100 | - | 1.00 | 5.33 |
(c) | 70 | 30 | 0.51 | 2.84 |
(d) | 100 | - | 0.97 | 5.44 |
(d) | 70 | 30 | 0.44 | 2.57 |
(e) | 100 | - | 1.19 | 6.27 |
(e) | 70 | 30 | 0.48 | 2.70 |
(f) | 100 | - | 1.12 | 6.01 |
(f) | 70 | 30 | 0.52 | 3.18 |
(g) | 100 | - | 0.70 | 3.97 |
(g) | 70 | 30 | 0.37 | 2.60 |
(h) | 100 | - | 1.24 | 6.72 |
(h) | 70 | 30 | 0.47 | 2.93 |
(i) | 100 | - | 1.25 | 6.58 |
(i) | 70 | 30 | 0.48 | 2.98 |
(j) | 100 | - | 1.33 | 6.97 |
(j) | 70 | 30 | 0.50 | 3.00 |
(k) | 100 | - | 1.15 | 6.33 |
(k) | 70 | 30 | 0.40 | 2.51 |
(l) | 100 | - | 1.11 | 5.94 |
(l) | 70 | 30 | 0.39 | 2.78 |
(m) | 100 | - | 1.04 | 5.50 |
(m) | 70 | 30 | 0.36 | 2.46 |
Claims (18)
- 하기 화학식 1 및 화학식 2의 모노머를 유기용매 하에서 산 또는 염기 촉매와 물을 이용하여 가수분해 및 축합 반응시켜 제조되는 실록산계 수지.[화학식 1]상기 식에서 R1은 수소원자, C1∼C3의 알킬기 또는 C6∼C15의 아릴기이고, X1, X2, X3는 각각 독립적으로 C1∼C3의 알킬기, C1∼C10의 알콕시기, 또는 할로겐원자로서, 상기 X1, X2, X3중 적어도 하나는 가수분해가능한 작용기이며, m은 0∼10의 정수이고, p는 3∼8의 정수이다.[화학식 2]상기 식에서 R2은 각각 독립적으로 수소원자, C1∼C3의 알킬기 또는 C6∼C15의 아릴기이고, X4는 C1∼C10의 알콕시기이며, Y1은 C1∼C3의 알킬기 또는 C1∼C10의 알콕시기이고, n은 0 또는 1~10의 정수이다.
- 제 1항에 있어서, 상기 화학식 1의 모노머와 상기 화학식 2의 모노머의 몰비가 1:99∼99:1인 것을 특징으로 하는 실록산계 수지.
- 제 1항에 있어서, 상기 산 또는 염기 촉매가 염산(hydrochloric acid), 질산(nitric acid), 벤젠 술폰산(benzene sulfonic acid), 옥살릭산(oxalic acid), 포름산(formic acid), 수산화칼륨(potassium hydroxide), 수산화나트륨(sodium hydroxide), 트리에틸아민(triethylamine), 탄산수소나트륨(sodium bicarbonate),또는 피리딘(pyridine)인 것을 특징으로 하는 실록산계 수지.
- 제 1항에 있어서, 상기 모노머와 산 또는 염기 촉매의 몰비가 1:0.000001∼1:10의 범위인 것을 특징으로 하는 실록산계 수지.
- 제 1항에 있어서, 상기 모노머와 물의 몰비가 1:1∼1:1000의 범위인 것을 특징으로 하는 실록산계 수지.
- 제 1항에 있어서, 상기 축합 반응 및 가수분해 반응이 0∼200℃에서 0.1∼100 시간 진행되는 것을 특징으로 하는 실록산계 수지.
- 제 1항에 있어서, 상기 유기용매로는 지방족 탄화수소 용매, 방향족 탄화수소 용매, 케톤계 용매, 에테르계 용매, 아세테이트계 용매, 알코올계 용매, 아미드계 용매, 실리콘계 용매 또는 이들의 혼합물을 사용하는 것을 특징으로 하는 실록산계 수지.
- 제 1항에 있어서, 상기 수지의 중량평균 분자량이 3,000∼300,000의 범위가 되는 것을 특징으로 하는 실록산계 수지.
- 상기 제 1항의 실록산계 수지를 유기용매에 녹여서 실리콘 기판 위에 코팅한 후, 열 경화시키는 단계를 포함하는 반도체 층간 절연막의 형성방법.
- 제 9항에 있어서, 상기 실록산계 수지 고형분 무게에 대해 1∼70 중량% 함량으로 기공형성물질을 혼합하는 것을 특징으로 하는 반도체 층간 절연막의 형성방법.
- 제 9항에 있어서, 상기 기공 형성물질이 덱스트린(cyclodextrin), 폴리카프로락톤(polycaprolactone) 또는 그의 유도체인 것을 특징으로 하는 반도체 층간 절연막의 형성방법.
- 제 9항에 있어서, 상기 유기용매로는 지방족 탄화수소 용매, 방향족 탄화수소 용매, 케톤계 용매, 에테르계 용매, 아세테이트계 용매, 알코올계 용매, 아미드계 용매, 실리콘계 용매 또는 이들의 혼합물을 사용하는 것을 특징으로 하는 반도체 층간 절연막의 형성방법.
- 제 9항에 있어서, 상기 유기용매가 실록산계 수지와 기공형성 물질을 포함하는 고형분 무게에 대해 20∼99.9 중량% 범위에서 사용되는 것을 특징으로 하는 반도체 층간 절연막의 형성 방법.
- 제 9항에 있어서, 상기 실록산계 수지가 스핀코팅을 통해 도포되는 것을 특징으로 하는 반도체 층간 절연막의 형성방법.
- 제 9항에 있어서, 상기 열 경화가 150∼600℃에서 1∼150분 동안 진행되는 것을 특징으로 하는 반도체 층간 절연막의 형성방법.
- 제 1항에 의한 실록산계 수지로 이루어지 반도체 층간 절연막.
- 제 16항에 있어서, 기공 형성 물질에 의해 미세기공이 형성된 것을 특징으로 하는 반도체 층간 절연막.
- 제 16항에 있어서, 상기 기공 형성물질로 덱스트린(cyclodextrin), 폴리카프로락톤(polycaprolactone) 또는 그의 유도체가 사용된 것을 특징으로 하는 반도체 층간 절연막.
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US10/695,777 US7014917B2 (en) | 2003-06-02 | 2003-10-30 | Siloxane-based resin and interlayer insulating film for a semiconductor device made using the same |
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DE200460018426 DE602004018426D1 (de) | 2003-06-02 | 2004-05-27 | Siloxanbasiertes Harz und isolierende Zwischenschicht daraus für Halbleiteranwendungen |
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KR20060090483A (ko) * | 2005-02-07 | 2006-08-11 | 삼성코닝 주식회사 | 풀러렌을 포함하는 저유전 박막 형성용 조성물, 이를이용한 저유전 박막 및 저유전 박막의 제조방법 |
KR101078150B1 (ko) * | 2005-03-17 | 2011-10-28 | 삼성전자주식회사 | 유기-무기 복합체 다공성 물질을 이용한 비휘발성 나노 채널 메모리 소자 |
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US6623711B2 (en) * | 2001-03-27 | 2003-09-23 | Samsung Electronics Co., Ltd. | Siloxane-based resin and method for forming insulating film between interconnect layers in semiconductor devices by using the same |
KR100507967B1 (ko) * | 2003-07-01 | 2005-08-10 | 삼성전자주식회사 | 실록산계 수지 및 이를 이용한 반도체 층간 절연막 |
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EP1484354B1 (en) | 2008-12-17 |
US20040242013A1 (en) | 2004-12-02 |
DE602004018426D1 (de) | 2009-01-29 |
CN100422241C (zh) | 2008-10-01 |
EP1484354A1 (en) | 2004-12-08 |
US7014917B2 (en) | 2006-03-21 |
JP2004359953A (ja) | 2004-12-24 |
CN1572816A (zh) | 2005-02-02 |
KR100506695B1 (ko) | 2005-08-08 |
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