TWI252232B - Organosilane-containing material for insulation film, method for producing the same, and semiconductor device - Google Patents
Organosilane-containing material for insulation film, method for producing the same, and semiconductor device Download PDFInfo
- Publication number
- TWI252232B TWI252232B TW92102012A TW92102012A TWI252232B TW I252232 B TWI252232 B TW I252232B TW 92102012 A TW92102012 A TW 92102012A TW 92102012 A TW92102012 A TW 92102012A TW I252232 B TWI252232 B TW I252232B
- Authority
- TW
- Taiwan
- Prior art keywords
- atom
- decane
- insulating film
- general formula
- lithium
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 45
- 239000004065 semiconductor Substances 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 32
- 238000009413 insulation Methods 0.000 title abstract description 7
- 150000001282 organosilanes Chemical class 0.000 title 1
- -1 halogenated alkoxy silane Chemical compound 0.000 claims abstract description 116
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 63
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 44
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 16
- 150000004820 halides Chemical class 0.000 claims abstract description 14
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 13
- 238000005229 chemical vapour deposition Methods 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 106
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 27
- 229910052707 ruthenium Inorganic materials 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 19
- 150000002641 lithium Chemical group 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000001979 organolithium group Chemical group 0.000 claims description 11
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 239000004576 sand Substances 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims description 7
- 239000002923 metal particle Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000002015 acyclic group Chemical group 0.000 claims 2
- NPPYJNHHSNNWGU-UHFFFAOYSA-N C(CCCC)[Ru] Chemical compound C(CCCC)[Ru] NPPYJNHHSNNWGU-UHFFFAOYSA-N 0.000 claims 1
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- 241000720287 Decapterus tabl Species 0.000 claims 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 14
- 239000002184 metal Substances 0.000 abstract description 14
- 239000011229 interlayer Substances 0.000 abstract description 9
- 229910000077 silane Inorganic materials 0.000 abstract 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 50
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 42
- 125000001183 hydrocarbyl group Chemical group 0.000 description 36
- 150000001721 carbon Chemical group 0.000 description 31
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 229910052749 magnesium Inorganic materials 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000006227 byproduct Substances 0.000 description 13
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 11
- WJMXTYZCTXTFJM-UHFFFAOYSA-N 1,1,1,2-tetraethoxydecane Chemical compound C(C)OC(C(OCC)(OCC)OCC)CCCCCCCC WJMXTYZCTXTFJM-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000002734 organomagnesium group Chemical group 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229930195734 saturated hydrocarbon Natural products 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 7
- GHTQBJZRHNNLIS-UHFFFAOYSA-N C(CCC)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(CCC)C(C(OC)(OC)OC)CCCCCCCC GHTQBJZRHNNLIS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- FPYZFGNMCPBDBU-UHFFFAOYSA-N C(CCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical group C(CCC)C(C(OCC)(OCC)OCC)CCCCCCCC FPYZFGNMCPBDBU-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- NCRNCSZWOOYBQF-UHFFFAOYSA-N 1,1-Dimethoxydecane Chemical compound CCCCCCCCCC(OC)OC NCRNCSZWOOYBQF-UHFFFAOYSA-N 0.000 description 4
- GDDPLWAEEWIQKZ-UHFFFAOYSA-N 1,1-diethoxydecane Chemical compound CCCCCCCCCC(OCC)OCC GDDPLWAEEWIQKZ-UHFFFAOYSA-N 0.000 description 4
- LOLANUHFGPZTLQ-UHFFFAOYSA-N 1-ethoxydecane Chemical compound CCCCCCCCCCOCC LOLANUHFGPZTLQ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- OZNXTQSXSHODFR-UHFFFAOYSA-N 1-chloroadamantane Chemical compound C1C(C2)CC3CC2CC1(Cl)C3 OZNXTQSXSHODFR-UHFFFAOYSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- ZBUAUEGAVBBRQH-UHFFFAOYSA-N C(CCC)C(C(OCC)(C)C)CCCCCCCC Chemical compound C(CCC)C(C(OCC)(C)C)CCCCCCCC ZBUAUEGAVBBRQH-UHFFFAOYSA-N 0.000 description 3
- BEAZKAJXLFKZSC-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)C(C(OC)(OC)C23CC1CC(CC(C2)C1)C3)CCCCCCCC Chemical compound C12(CC3CC(CC(C1)C3)C2)C(C(OC)(OC)C23CC1CC(CC(C2)C1)C3)CCCCCCCC BEAZKAJXLFKZSC-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ONKWMRZMIGGFOJ-UHFFFAOYSA-N [Li].[Ru] Chemical compound [Li].[Ru] ONKWMRZMIGGFOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 238000010813 internal standard method Methods 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002901 organomagnesium compounds Chemical class 0.000 description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- ANBBCZAIOXDZPV-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methyldecane Chemical compound CC(C(OC)(OC)OC)CCCCCCCC ANBBCZAIOXDZPV-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 2
- JPEWDCTZJFUITH-UHFFFAOYSA-N 1-methoxydecane Chemical compound CCCCCCCCCCOC JPEWDCTZJFUITH-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- USVBOGGVFRZJKP-UHFFFAOYSA-N C(C)(C)(C)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(C)(C)(C)C(C(OC)(OC)OC)CCCCCCCC USVBOGGVFRZJKP-UHFFFAOYSA-N 0.000 description 2
- MMDGRTPRMVCQOD-UHFFFAOYSA-N C(CCC)C(C(OC)(C)C)CCCCCCCC Chemical group C(CCC)C(C(OC)(C)C)CCCCCCCC MMDGRTPRMVCQOD-UHFFFAOYSA-N 0.000 description 2
- UTBZWMMMTOCAQO-UHFFFAOYSA-N C(CCC)C(C(OCC)(OCC)C)CCCCCCCC Chemical compound C(CCC)C(C(OCC)(OCC)C)CCCCCCCC UTBZWMMMTOCAQO-UHFFFAOYSA-N 0.000 description 2
- RRXMMBCPYKWDCY-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)C(C(OCC)(OCC)C23CC1CC(CC(C2)C1)C3)CCCCCCCC Chemical compound C12(CC3CC(CC(C1)C3)C2)C(C(OCC)(OCC)C23CC1CC(CC(C2)C1)C3)CCCCCCCC RRXMMBCPYKWDCY-UHFFFAOYSA-N 0.000 description 2
- FUHFSPLITPAXIO-UHFFFAOYSA-N CC(C)OCCCCCCCCCC(Cl)(Cl)Cl Chemical compound CC(C)OCCCCCCCCCC(Cl)(Cl)Cl FUHFSPLITPAXIO-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFOFVZJNIUBUQN-UHFFFAOYSA-N Cl.COC(CCCCCCCCC)(OC)OC Chemical compound Cl.COC(CCCCCCCCC)(OC)OC UFOFVZJNIUBUQN-UHFFFAOYSA-N 0.000 description 2
- GBLOQUAVUBWOHF-UHFFFAOYSA-N ClC(C(OC)(OC)Cl)CCCCCCCC Chemical compound ClC(C(OC)(OC)Cl)CCCCCCCC GBLOQUAVUBWOHF-UHFFFAOYSA-N 0.000 description 2
- KODWSEHMQLBTPK-UHFFFAOYSA-N ClC(C(OCC)(OCC)Cl)CCCCCCCC Chemical compound ClC(C(OCC)(OCC)Cl)CCCCCCCC KODWSEHMQLBTPK-UHFFFAOYSA-N 0.000 description 2
- HUSRXPLXMLMACT-UHFFFAOYSA-N ClC(COCCCCCCCCCC)(Cl)Cl Chemical compound ClC(COCCCCCCCCCC)(Cl)Cl HUSRXPLXMLMACT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- XUXRZLFDDRKSGX-UHFFFAOYSA-N [Cl-].C(C)(C)(C)[PH+](C)C Chemical compound [Cl-].C(C)(C)(C)[PH+](C)C XUXRZLFDDRKSGX-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 2
- DBKDYYFPDRPMPE-UHFFFAOYSA-N lithium;cyclopenta-1,3-diene Chemical compound [Li+].C=1C=C[CH-]C=1 DBKDYYFPDRPMPE-UHFFFAOYSA-N 0.000 description 2
- HAUKUGBTJXWQMF-UHFFFAOYSA-N lithium;propan-2-olate Chemical compound [Li+].CC(C)[O-] HAUKUGBTJXWQMF-UHFFFAOYSA-N 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 150000002900 organolithium compounds Chemical class 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011882 ultra-fine particle Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- WMUAATXSLGPPEO-UHFFFAOYSA-N (1-cyclopentyl-1,1-dimethoxydecan-2-yl)cyclopentane Chemical compound C1(CCCC1)C(C(OC)(OC)C1CCCC1)CCCCCCCC WMUAATXSLGPPEO-UHFFFAOYSA-N 0.000 description 1
- FRGJFERYCDBOQD-UHFFFAOYSA-N 1,1,1,2-tetrachlorodecane Chemical compound CCCCCCCCC(Cl)C(Cl)(Cl)Cl FRGJFERYCDBOQD-UHFFFAOYSA-N 0.000 description 1
- AGGJWJFEEKIYOF-UHFFFAOYSA-N 1,1,1-triethoxydecane Chemical compound CCCCCCCCCC(OCC)(OCC)OCC AGGJWJFEEKIYOF-UHFFFAOYSA-N 0.000 description 1
- VNPQQEYMXYCAEZ-UHFFFAOYSA-N 1,2,3,4-tetramethylcyclopenta-1,3-diene Chemical compound CC1=C(C)C(C)=C(C)C1 VNPQQEYMXYCAEZ-UHFFFAOYSA-N 0.000 description 1
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 description 1
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
- VQHPRVYDKRESCL-UHFFFAOYSA-N 1-bromoadamantane Chemical compound C1C(C2)CC3CC2CC1(Br)C3 VQHPRVYDKRESCL-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical class CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 description 1
- ZFSFKYIBIOKXKI-UHFFFAOYSA-N 1-ethyl-1-methylhydrazine Chemical compound CCN(C)N ZFSFKYIBIOKXKI-UHFFFAOYSA-N 0.000 description 1
- PXVOATXCSSPUEM-UHFFFAOYSA-N 1-iodoadamantane Chemical compound C1C(C2)CC3CC2CC1(I)C3 PXVOATXCSSPUEM-UHFFFAOYSA-N 0.000 description 1
- NHXCUKIHMLHWQT-UHFFFAOYSA-N 1-propoxydecane Chemical class CCCCCCCCCCOCCC NHXCUKIHMLHWQT-UHFFFAOYSA-N 0.000 description 1
- GCZWJRLXIPVNLU-UHFFFAOYSA-N 2,2-dimethoxy-3-methylundecane Chemical compound CC(C(OC)(OC)C)CCCCCCCC GCZWJRLXIPVNLU-UHFFFAOYSA-N 0.000 description 1
- QDKSGHXRHXVMPF-UHFFFAOYSA-N 2,2-dimethylundecane Chemical compound CCCCCCCCCC(C)(C)C QDKSGHXRHXVMPF-UHFFFAOYSA-N 0.000 description 1
- KSEZCOKVNUNDJB-UHFFFAOYSA-N 2,3,3-trimethylundecan-2-ol Chemical compound CCCCCCCCC(C)(C)C(C)(C)O KSEZCOKVNUNDJB-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical group CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- JJCWKVUUIFLXNZ-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCO JJCWKVUUIFLXNZ-UHFFFAOYSA-M 0.000 description 1
- JJCSHDJYJIBTNM-UHFFFAOYSA-N 3,3-diethoxydodecane Chemical compound CCCCCCCCCC(CC)(OCC)OCC JJCSHDJYJIBTNM-UHFFFAOYSA-N 0.000 description 1
- CFSRYSNJOVVGIH-UHFFFAOYSA-N 3-(trichloromethyl)undec-1-ene Chemical compound C(=C)C(C(Cl)(Cl)Cl)CCCCCCCC CFSRYSNJOVVGIH-UHFFFAOYSA-N 0.000 description 1
- LBIHNTAFJVHBLJ-UHFFFAOYSA-N 3-(triethoxymethyl)undec-1-ene Chemical compound C(=C)C(C(OCC)(OCC)OCC)CCCCCCCC LBIHNTAFJVHBLJ-UHFFFAOYSA-N 0.000 description 1
- IIEWMRPKJCXTAD-UHFFFAOYSA-N 3-(trimethoxymethyl)undecane Chemical compound C(C)C(C(OC)(OC)OC)CCCCCCCC IIEWMRPKJCXTAD-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical group C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- QUFDPCUVWVVZIF-UHFFFAOYSA-N C(=C)C(C(Cl)(Cl)C=C)CCCCCCCC Chemical compound C(=C)C(C(Cl)(Cl)C=C)CCCCCCCC QUFDPCUVWVVZIF-UHFFFAOYSA-N 0.000 description 1
- JZHKIUBMQMDQRG-UHFFFAOYSA-N C(=C)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)OC)CCCCCCCC JZHKIUBMQMDQRG-UHFFFAOYSA-N 0.000 description 1
- MWCBUBBNIMNWFT-UHFFFAOYSA-N C(C)(C)(C)C(C(O)(O)C1=CC=CC=C1)CCCCCCCC Chemical compound C(C)(C)(C)C(C(O)(O)C1=CC=CC=C1)CCCCCCCC MWCBUBBNIMNWFT-UHFFFAOYSA-N 0.000 description 1
- BPTVOSVTPLZUJQ-UHFFFAOYSA-N C(C)(C)(C)C(C(OC(C)C)(OC(C)C)C(C)(C)C)CCCCCCCC Chemical compound C(C)(C)(C)C(C(OC(C)C)(OC(C)C)C(C)(C)C)CCCCCCCC BPTVOSVTPLZUJQ-UHFFFAOYSA-N 0.000 description 1
- ZPEFNJUZEBNPPZ-UHFFFAOYSA-N C(C)(C)(C)C(C(OC)(OC)C(C)(C)C)CCCCCCCC Chemical compound C(C)(C)(C)C(C(OC)(OC)C(C)(C)C)CCCCCCCC ZPEFNJUZEBNPPZ-UHFFFAOYSA-N 0.000 description 1
- OWFGSRKLLAIWCL-UHFFFAOYSA-N C(C)(C)(C)C(C(OC)(OC)CC)CCCCCCCC Chemical compound C(C)(C)(C)C(C(OC)(OC)CC)CCCCCCCC OWFGSRKLLAIWCL-UHFFFAOYSA-N 0.000 description 1
- DXIHVAWZQXUNHG-UHFFFAOYSA-N C(C)(C)(C)C(C(OCC)(OCC)C(C)(C)C)CCCCCCCC Chemical compound C(C)(C)(C)C(C(OCC)(OCC)C(C)(C)C)CCCCCCCC DXIHVAWZQXUNHG-UHFFFAOYSA-N 0.000 description 1
- VWFVNYYIDHXXBH-UHFFFAOYSA-N C(C)(C)(C)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(C)(C)(C)C(C(OCC)(OCC)OCC)CCCCCCCC VWFVNYYIDHXXBH-UHFFFAOYSA-N 0.000 description 1
- OVAITXFBTNFCRI-UHFFFAOYSA-N C(C)(C)(C)OC(C(OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)CCCCCCCC Chemical compound C(C)(C)(C)OC(C(OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)CCCCCCCC OVAITXFBTNFCRI-UHFFFAOYSA-N 0.000 description 1
- MWNRZTCEWSRFPZ-UHFFFAOYSA-N C(C)(C)C(C(OCC)(OCC)C(C)C)CCCCCCCC Chemical compound C(C)(C)C(C(OCC)(OCC)C(C)C)CCCCCCCC MWNRZTCEWSRFPZ-UHFFFAOYSA-N 0.000 description 1
- AWDKVIUUINUYAI-UHFFFAOYSA-N C(C)(C)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(C)(C)C(C(OCC)(OCC)OCC)CCCCCCCC AWDKVIUUINUYAI-UHFFFAOYSA-N 0.000 description 1
- GZHUXNHSWHXKFK-UHFFFAOYSA-N C(C)(C)C(CCCCCCCCC)(OC)C(C)C Chemical compound C(C)(C)C(CCCCCCCCC)(OC)C(C)C GZHUXNHSWHXKFK-UHFFFAOYSA-N 0.000 description 1
- LTKHYTHKJLJJSX-UHFFFAOYSA-N C(C)(CC)C(C(OC)(OC)C(C)CC)CCCCCCCC Chemical group C(C)(CC)C(C(OC)(OC)C(C)CC)CCCCCCCC LTKHYTHKJLJJSX-UHFFFAOYSA-N 0.000 description 1
- XCVHMBQRPKAJEQ-UHFFFAOYSA-N C(C)(CC)C(C(OCC)(OCC)C(C)CC)CCCCCCCC Chemical group C(C)(CC)C(C(OCC)(OCC)C(C)CC)CCCCCCCC XCVHMBQRPKAJEQ-UHFFFAOYSA-N 0.000 description 1
- XEPAKJGFUVCJOW-UHFFFAOYSA-N C(C)C(C(OCC)(OCC)CC)CCCCCCCC Chemical compound C(C)C(C(OCC)(OCC)CC)CCCCCCCC XEPAKJGFUVCJOW-UHFFFAOYSA-N 0.000 description 1
- MHOROQWKQRSSHY-UHFFFAOYSA-N C(CCC)C(C(OC(C)C)(OC(C)C)OC(C)C)CCCCCCCC Chemical compound C(CCC)C(C(OC(C)C)(OC(C)C)OC(C)C)CCCCCCCC MHOROQWKQRSSHY-UHFFFAOYSA-N 0.000 description 1
- ZOQBHMUBCNQVKJ-UHFFFAOYSA-N C(CCC)C(C(OC)(CC)CC)CCCCCCCC Chemical group C(CCC)C(C(OC)(CC)CC)CCCCCCCC ZOQBHMUBCNQVKJ-UHFFFAOYSA-N 0.000 description 1
- SNJJQURHHCVHJD-UHFFFAOYSA-N C(CCC)C(C(OC)(OC)C)CCCCCCCC Chemical compound C(CCC)C(C(OC)(OC)C)CCCCCCCC SNJJQURHHCVHJD-UHFFFAOYSA-N 0.000 description 1
- IPJPUAUTJOZPEA-UHFFFAOYSA-N C(CCC)C(C(OC)(OC)CC)CCCCCCCC Chemical group C(CCC)C(C(OC)(OC)CC)CCCCCCCC IPJPUAUTJOZPEA-UHFFFAOYSA-N 0.000 description 1
- BLYPOGXWGCJFTQ-UHFFFAOYSA-N C(CCC)C(C(OC)(OC)OC)(CCCCCCCC)CCCC Chemical compound C(CCC)C(C(OC)(OC)OC)(CCCCCCCC)CCCC BLYPOGXWGCJFTQ-UHFFFAOYSA-N 0.000 description 1
- RWWWFNWAXMGWNW-UHFFFAOYSA-N C(CCC)C(CCCCCCCCC)(OCC)CCCC Chemical compound C(CCC)C(CCCCCCCCC)(OCC)CCCC RWWWFNWAXMGWNW-UHFFFAOYSA-N 0.000 description 1
- NXWWIQKBVXPMKR-UHFFFAOYSA-N C(CCCC)C(C(OC(C)C)(OC(C)C)OC(C)C)CCCCCCCC Chemical compound C(CCCC)C(C(OC(C)C)(OC(C)C)OC(C)C)CCCCCCCC NXWWIQKBVXPMKR-UHFFFAOYSA-N 0.000 description 1
- BPDIDNOQBXCJJL-UHFFFAOYSA-N C(CCCC)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(CCCC)C(C(OC)(OC)OC)CCCCCCCC BPDIDNOQBXCJJL-UHFFFAOYSA-N 0.000 description 1
- RDAJSLMSQSSYML-UHFFFAOYSA-N C(CCCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CCCC)C(C(OCC)(OCC)OCC)CCCCCCCC RDAJSLMSQSSYML-UHFFFAOYSA-N 0.000 description 1
- OQQRSXPTKJQZOI-UHFFFAOYSA-N C(CCCCCCCCC)OC(Cl)(Cl)Cl Chemical compound C(CCCCCCCCC)OC(Cl)(Cl)Cl OQQRSXPTKJQZOI-UHFFFAOYSA-N 0.000 description 1
- JSGRIFNBTXDZQU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC JSGRIFNBTXDZQU-UHFFFAOYSA-N 0.000 description 1
- VFXBUDUSFLYBOS-UHFFFAOYSA-N C1(=CC=CC=C1)C(CCCCCCCCC)(OC)OC Chemical compound C1(=CC=CC=C1)C(CCCCCCCCC)(OC)OC VFXBUDUSFLYBOS-UHFFFAOYSA-N 0.000 description 1
- CXVAGYHSZCTING-UHFFFAOYSA-N C1(=CCCCC1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CCCCC1)C(C(OC)(OC)OC)CCCCCCCC CXVAGYHSZCTING-UHFFFAOYSA-N 0.000 description 1
- XDQMLVQONPKQRK-UHFFFAOYSA-N C1(C=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(C=CC=C1)C(C(OC)(OC)OC)CCCCCCCC XDQMLVQONPKQRK-UHFFFAOYSA-N 0.000 description 1
- KYZCLJABKJZZCW-UHFFFAOYSA-N C1(C=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(C=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC KYZCLJABKJZZCW-UHFFFAOYSA-N 0.000 description 1
- KICDFSWSEOEJQZ-UHFFFAOYSA-N C1(CCCC1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(CCCC1)C(C(OC)(OC)OC)CCCCCCCC KICDFSWSEOEJQZ-UHFFFAOYSA-N 0.000 description 1
- ADQJGCLMVZSYKP-UHFFFAOYSA-N C1(CCCC1)C(C(OCC)(C)C)CCCCCCCC Chemical compound C1(CCCC1)C(C(OCC)(C)C)CCCCCCCC ADQJGCLMVZSYKP-UHFFFAOYSA-N 0.000 description 1
- INCDKSMMDMVUOH-UHFFFAOYSA-N C1(CCCC1)C(C(OCC)(OCC)C1CCCC1)CCCCCCCC Chemical compound C1(CCCC1)C(C(OCC)(OCC)C1CCCC1)CCCCCCCC INCDKSMMDMVUOH-UHFFFAOYSA-N 0.000 description 1
- FYXCLMAULNDNEI-UHFFFAOYSA-N C1(CCCC1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(CCCC1)C(C(OCC)(OCC)OCC)CCCCCCCC FYXCLMAULNDNEI-UHFFFAOYSA-N 0.000 description 1
- VLFHFQGASNOVAY-UHFFFAOYSA-N C1(CCCC1)C(OCCCCCCCCCC)(C1CCCC1)C1CCCC1 Chemical compound C1(CCCC1)C(OCCCCCCCCCC)(C1CCCC1)C1CCCC1 VLFHFQGASNOVAY-UHFFFAOYSA-N 0.000 description 1
- KIVWVLPBECDERK-UHFFFAOYSA-N C1(CCCC1)CC(CCCCCCCCC)(OC)OC Chemical compound C1(CCCC1)CC(CCCCCCCCC)(OC)OC KIVWVLPBECDERK-UHFFFAOYSA-N 0.000 description 1
- METMZQLCHZRPHN-UHFFFAOYSA-N C1(CCCC1)CCC(CCCCCCCCC)(OC)OC Chemical compound C1(CCCC1)CCC(CCCCCCCCC)(OC)OC METMZQLCHZRPHN-UHFFFAOYSA-N 0.000 description 1
- JWPHWFCPUQHFIZ-UHFFFAOYSA-N C1(CCCCC1)C(C(OC)(OC)C1CCCCC1)CCCCCCCC Chemical compound C1(CCCCC1)C(C(OC)(OC)C1CCCCC1)CCCCCCCC JWPHWFCPUQHFIZ-UHFFFAOYSA-N 0.000 description 1
- XGCSFAPCYMNGEJ-UHFFFAOYSA-N C1(CCCCC1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(CCCCC1)C(C(OC)(OC)OC)CCCCCCCC XGCSFAPCYMNGEJ-UHFFFAOYSA-N 0.000 description 1
- BSTTYKFEZPFBSB-UHFFFAOYSA-N C1(CCCCC1)C(C(OCC)(OCC)C1CCCCC1)CCCCCCCC Chemical compound C1(CCCCC1)C(C(OCC)(OCC)C1CCCCC1)CCCCCCCC BSTTYKFEZPFBSB-UHFFFAOYSA-N 0.000 description 1
- CKZRZYXNAOOMJD-UHFFFAOYSA-N C1(CCCCC1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(CCCCC1)C(C(OCC)(OCC)OCC)CCCCCCCC CKZRZYXNAOOMJD-UHFFFAOYSA-N 0.000 description 1
- PQVVWMPAWFHWDB-UHFFFAOYSA-N C1(CCCCC1)C(COCCCCCCCCCC)(C1CCCCC1)C1CCCCC1 Chemical compound C1(CCCCC1)C(COCCCCCCCCCC)(C1CCCCC1)C1CCCCC1 PQVVWMPAWFHWDB-UHFFFAOYSA-N 0.000 description 1
- ZHXUIQOHGPCPET-UHFFFAOYSA-N C1(CCCCC1)C(OCCCCCCCCCC)(C1CCCCC1)C1CCCCC1 Chemical compound C1(CCCCC1)C(OCCCCCCCCCC)(C1CCCCC1)C1CCCCC1 ZHXUIQOHGPCPET-UHFFFAOYSA-N 0.000 description 1
- CQKQCLAVJUYNCE-UHFFFAOYSA-N C1(CCCCC1)CC(CCCCCCCCC)(OC)OC Chemical compound C1(CCCCC1)CC(CCCCCCCCC)(OC)OC CQKQCLAVJUYNCE-UHFFFAOYSA-N 0.000 description 1
- VOCXRKOXCRMAQY-UHFFFAOYSA-N C1(CCCCC1)CC(CCCCCCCCC)(OCC)OCC Chemical compound C1(CCCCC1)CC(CCCCCCCCC)(OCC)OCC VOCXRKOXCRMAQY-UHFFFAOYSA-N 0.000 description 1
- GMLKASBTJKNVTR-UHFFFAOYSA-N C1(CCCCC1)CCC(CCCCCCCCC)(OC)OC Chemical compound C1(CCCCC1)CCC(CCCCCCCCC)(OC)OC GMLKASBTJKNVTR-UHFFFAOYSA-N 0.000 description 1
- NFFDRNMESXSYHG-UHFFFAOYSA-N C1(CCCCC1)CCC(CCCCCCCCC)(OCC)OCC Chemical compound C1(CCCCC1)CCC(CCCCCCCCC)(OCC)OCC NFFDRNMESXSYHG-UHFFFAOYSA-N 0.000 description 1
- ACSFSGORTGKAJW-UHFFFAOYSA-N C1C(C2)CC3CC2CC1([Li])C3 Chemical compound C1C(C2)CC3CC2CC1([Li])C3 ACSFSGORTGKAJW-UHFFFAOYSA-N 0.000 description 1
- PCJYZQMDOPASBT-UHFFFAOYSA-N CC(CC)OC(C(OC(C)CC)(OC(C)CC)OC(C)CC)CCCCCCCC Chemical compound CC(CC)OC(C(OC(C)CC)(OC(C)CC)OC(C)CC)CCCCCCCC PCJYZQMDOPASBT-UHFFFAOYSA-N 0.000 description 1
- MBRBMFVCYQFCKJ-UHFFFAOYSA-N CC1=C(C(=C(C=2CC3=CC=CC=C3C12)OC)OC)C Chemical compound CC1=C(C(=C(C=2CC3=CC=CC=C3C12)OC)OC)C MBRBMFVCYQFCKJ-UHFFFAOYSA-N 0.000 description 1
- QEVKCADVKNFKEP-UHFFFAOYSA-N CCCCCCCCC(C(C)(C)C)C(C)(C)OC Chemical compound CCCCCCCCC(C(C)(C)C)C(C)(C)OC QEVKCADVKNFKEP-UHFFFAOYSA-N 0.000 description 1
- NTAWHXNCNHAVJE-UHFFFAOYSA-N CCCCCCCCC(C(C)(C)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC Chemical compound CCCCCCCCC(C(C)(C)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC NTAWHXNCNHAVJE-UHFFFAOYSA-N 0.000 description 1
- ROGOZIHNXMQIHY-UHFFFAOYSA-N CCCCCCCCC(C(C)(C)C)C(C1=CC=CC=C1)(C2=CC=CC=C2)OC Chemical compound CCCCCCCCC(C(C)(C)C)C(C1=CC=CC=C1)(C2=CC=CC=C2)OC ROGOZIHNXMQIHY-UHFFFAOYSA-N 0.000 description 1
- CVXGTXIUKBRUIW-UHFFFAOYSA-N CCCCCCCCC(C(C)(C)OC)C1=CCCCC1 Chemical compound CCCCCCCCC(C(C)(C)OC)C1=CCCCC1 CVXGTXIUKBRUIW-UHFFFAOYSA-N 0.000 description 1
- QVWVYUMEZCLMHK-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(C)(C)OC Chemical compound CCCCCCCCC(C(C)C)C(C)(C)OC QVWVYUMEZCLMHK-UHFFFAOYSA-N 0.000 description 1
- SUWCBAPHBNVYFJ-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(C)(C)OCC Chemical compound CCCCCCCCC(C(C)C)C(C)(C)OCC SUWCBAPHBNVYFJ-UHFFFAOYSA-N 0.000 description 1
- CMXPFBVXKSGLMQ-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)OC Chemical compound CCCCCCCCC(C(C)C)C(C1=CC=CC=C1)(C1=CC=CC=C1)OC CMXPFBVXKSGLMQ-UHFFFAOYSA-N 0.000 description 1
- GSMKHTOHCWACJS-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(C1=CC=CC=C1)(OC)OC Chemical compound CCCCCCCCC(C(C)C)C(C1=CC=CC=C1)(OC)OC GSMKHTOHCWACJS-UHFFFAOYSA-N 0.000 description 1
- KPXDPNVPQWPNQE-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(C1=CC=CC=C1)(OCC)OCC Chemical compound CCCCCCCCC(C(C)C)C(C1=CC=CC=C1)(OCC)OCC KPXDPNVPQWPNQE-UHFFFAOYSA-N 0.000 description 1
- ZZWMFOPWXAJYFX-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(CC)(CC)OC Chemical compound CCCCCCCCC(C(C)C)C(CC)(CC)OC ZZWMFOPWXAJYFX-UHFFFAOYSA-N 0.000 description 1
- GJLCPWGQANBBAX-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(CC)(CC)OCC Chemical compound CCCCCCCCC(C(C)C)C(CC)(CC)OCC GJLCPWGQANBBAX-UHFFFAOYSA-N 0.000 description 1
- FCAKYZSWJFYYQO-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(CC)(OC)OC Chemical compound CCCCCCCCC(C(C)C)C(CC)(OC)OC FCAKYZSWJFYYQO-UHFFFAOYSA-N 0.000 description 1
- KKBNRTOFJDUPNW-UHFFFAOYSA-N CCCCCCCCC(C(C)C)C(CC)(OCC)OCC Chemical compound CCCCCCCCC(C(C)C)C(CC)(OCC)OCC KKBNRTOFJDUPNW-UHFFFAOYSA-N 0.000 description 1
- CAIPFEIHJNDGMB-UHFFFAOYSA-N CCCCCCCCC(C(C1=CC=CC=C1)(C1=CC=CC=C1)OC)C1=CCCCC1 Chemical compound CCCCCCCCC(C(C1=CC=CC=C1)(C1=CC=CC=C1)OC)C1=CCCCC1 CAIPFEIHJNDGMB-UHFFFAOYSA-N 0.000 description 1
- JJNHYVYZTGCFKM-UHFFFAOYSA-N CCCCCCCCC(C(CC)(CC)OC)C1=CCCCC1 Chemical compound CCCCCCCCC(C(CC)(CC)OC)C1=CCCCC1 JJNHYVYZTGCFKM-UHFFFAOYSA-N 0.000 description 1
- FOOLIBBFXDYHQL-UHFFFAOYSA-N CCCCCCCCC(C1=CCCCC1)C(C)(OC)OC Chemical compound CCCCCCCCC(C1=CCCCC1)C(C)(OC)OC FOOLIBBFXDYHQL-UHFFFAOYSA-N 0.000 description 1
- WZFARKZXBNWIFA-UHFFFAOYSA-N CCCCCCCCC(C1=CCCCC1)C(C2=CC=CC=C2)(OC)OC Chemical compound CCCCCCCCC(C1=CCCCC1)C(C2=CC=CC=C2)(OC)OC WZFARKZXBNWIFA-UHFFFAOYSA-N 0.000 description 1
- RNDWUKYDRAYEGP-UHFFFAOYSA-N CCCCCCCCC(C1=CCCCC1)C(CC)(OC)OC Chemical compound CCCCCCCCC(C1=CCCCC1)C(CC)(OC)OC RNDWUKYDRAYEGP-UHFFFAOYSA-N 0.000 description 1
- UJURKGQHJQTDSW-UHFFFAOYSA-N CCCCCCCCC(C1C=CC=C1)C(C)(C)OC Chemical compound CCCCCCCCC(C1C=CC=C1)C(C)(C)OC UJURKGQHJQTDSW-UHFFFAOYSA-N 0.000 description 1
- LFZAVLQRPFGWJR-UHFFFAOYSA-N CCCCCCCCC(C1C=CC=C1)C(C)(C)OCC Chemical compound CCCCCCCCC(C1C=CC=C1)C(C)(C)OCC LFZAVLQRPFGWJR-UHFFFAOYSA-N 0.000 description 1
- PVUBMVVOSLXHJY-UHFFFAOYSA-N CCCCCCCCC(C1C=CC=C1)C(C)(OCC)OCC Chemical compound CCCCCCCCC(C1C=CC=C1)C(C)(OCC)OCC PVUBMVVOSLXHJY-UHFFFAOYSA-N 0.000 description 1
- IXAWYICSCGDXGE-UHFFFAOYSA-N CCCCCCCCC(C1C=CC=C1)C(C2=CC=CC=C2)(OC)OC Chemical compound CCCCCCCCC(C1C=CC=C1)C(C2=CC=CC=C2)(OC)OC IXAWYICSCGDXGE-UHFFFAOYSA-N 0.000 description 1
- JZRXVYRRINMRRF-UHFFFAOYSA-N CCCCCCCCC(C1C=CC=C1)C(CC)(CC)OC Chemical compound CCCCCCCCC(C1C=CC=C1)C(CC)(CC)OC JZRXVYRRINMRRF-UHFFFAOYSA-N 0.000 description 1
- GCZJQPOZGLEROT-UHFFFAOYSA-N CCCCCCCCC(C1C=CC=C1)C(CC)(CC)OCC Chemical compound CCCCCCCCC(C1C=CC=C1)C(CC)(CC)OCC GCZJQPOZGLEROT-UHFFFAOYSA-N 0.000 description 1
- WPYSTFKSWGBVLL-UHFFFAOYSA-N CCCCCCCCC(C1C=CC=C1)C(CC)(OCC)OCC Chemical compound CCCCCCCCC(C1C=CC=C1)C(CC)(OCC)OCC WPYSTFKSWGBVLL-UHFFFAOYSA-N 0.000 description 1
- DDFAKIVCLZSSAF-UHFFFAOYSA-N CCCCCCCCC(C1CCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OC Chemical compound CCCCCCCCC(C1CCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OC DDFAKIVCLZSSAF-UHFFFAOYSA-N 0.000 description 1
- GWXKBSUKDGCGIU-UHFFFAOYSA-N CCCCCCCCC(C1CCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC Chemical compound CCCCCCCCC(C1CCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC GWXKBSUKDGCGIU-UHFFFAOYSA-N 0.000 description 1
- BENVVHATNWLEJB-UHFFFAOYSA-N CCCCCCCCC(C1CCCC1)C(C2=CC=CC=C2)(OC)OC Chemical compound CCCCCCCCC(C1CCCC1)C(C2=CC=CC=C2)(OC)OC BENVVHATNWLEJB-UHFFFAOYSA-N 0.000 description 1
- JBPRPXASBPAWDJ-UHFFFAOYSA-N CCCCCCCCC(C1CCCC1)C(C2=CC=CC=C2)(OCC)OCC Chemical compound CCCCCCCCC(C1CCCC1)C(C2=CC=CC=C2)(OCC)OCC JBPRPXASBPAWDJ-UHFFFAOYSA-N 0.000 description 1
- IQSWURVVERVRFX-UHFFFAOYSA-N CCCCCCCCC(C1CCCC1)C(CC)(CC)OC Chemical compound CCCCCCCCC(C1CCCC1)C(CC)(CC)OC IQSWURVVERVRFX-UHFFFAOYSA-N 0.000 description 1
- IMPXXJIMFUWKTL-UHFFFAOYSA-N CCCCCCCCC(C1CCCCC1)C(C)(C)OC Chemical compound CCCCCCCCC(C1CCCCC1)C(C)(C)OC IMPXXJIMFUWKTL-UHFFFAOYSA-N 0.000 description 1
- XIPJPCSDKCBRDE-UHFFFAOYSA-N CCCCCCCCC(C1CCCCC1)C(C)(C)OCC Chemical compound CCCCCCCCC(C1CCCCC1)C(C)(C)OCC XIPJPCSDKCBRDE-UHFFFAOYSA-N 0.000 description 1
- JEMBMFISIFVAAG-UHFFFAOYSA-N CCCCCCCCC(C1CCCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OC Chemical compound CCCCCCCCC(C1CCCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OC JEMBMFISIFVAAG-UHFFFAOYSA-N 0.000 description 1
- JQYACARHILAJSX-UHFFFAOYSA-N CCCCCCCCC(C1CCCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC Chemical compound CCCCCCCCC(C1CCCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC JQYACARHILAJSX-UHFFFAOYSA-N 0.000 description 1
- QHBBVNWSFXZXOZ-UHFFFAOYSA-N CCCCCCCCC(C1CCCCC1)C(C2=CC=CC=C2)(OCC)OCC Chemical compound CCCCCCCCC(C1CCCCC1)C(C2=CC=CC=C2)(OCC)OCC QHBBVNWSFXZXOZ-UHFFFAOYSA-N 0.000 description 1
- NTOXOYGTKBGMCC-UHFFFAOYSA-N CCCCCCCCC(C1CCCCC1)C(CC)(CC)OC Chemical compound CCCCCCCCC(C1CCCCC1)C(CC)(CC)OC NTOXOYGTKBGMCC-UHFFFAOYSA-N 0.000 description 1
- QKWPDVBVBXJNQF-UHFFFAOYSA-N CCCCCCCCC(C1CCCCC1)C(CC)(CC)OCC Chemical compound CCCCCCCCC(C1CCCCC1)C(CC)(CC)OCC QKWPDVBVBXJNQF-UHFFFAOYSA-N 0.000 description 1
- LHMJSXGSGWGFMC-UHFFFAOYSA-N CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC Chemical group CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(C1=CC=CC=C1)OCC LHMJSXGSGWGFMC-UHFFFAOYSA-N 0.000 description 1
- HEGNHSOFFRPFPQ-UHFFFAOYSA-N CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(C2=CC=CC=C2)OC Chemical group CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(C2=CC=CC=C2)OC HEGNHSOFFRPFPQ-UHFFFAOYSA-N 0.000 description 1
- CDEUJPRBFSXDGO-UHFFFAOYSA-N CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(OC)OC Chemical group CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(OC)OC CDEUJPRBFSXDGO-UHFFFAOYSA-N 0.000 description 1
- UUNHAAZDDDADQX-UHFFFAOYSA-N CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(OCC)OCC Chemical group CCCCCCCCC(CCCC)C(C1=CC=CC=C1)(OCC)OCC UUNHAAZDDDADQX-UHFFFAOYSA-N 0.000 description 1
- OALARUJJSFAMLG-UHFFFAOYSA-N CCCCCCCCC(CCCC)C(CC)(CC)OCC Chemical group CCCCCCCCC(CCCC)C(CC)(CC)OCC OALARUJJSFAMLG-UHFFFAOYSA-N 0.000 description 1
- YPDRGQNXVMEONT-UHFFFAOYSA-N CCCCCCCCC(CCCC)C(CC)(OCC)OCC Chemical group CCCCCCCCC(CCCC)C(CC)(OCC)OCC YPDRGQNXVMEONT-UHFFFAOYSA-N 0.000 description 1
- SDKDSVRSDCHBFL-UHFFFAOYSA-N CCCCCCCCCC(C1CCCC1)OCC Chemical compound CCCCCCCCCC(C1CCCC1)OCC SDKDSVRSDCHBFL-UHFFFAOYSA-N 0.000 description 1
- ODZKSQBRXBCWSX-UHFFFAOYSA-N CCCCCCCCCC(CC1C=CC=C1)(OC)OC Chemical compound CCCCCCCCCC(CC1C=CC=C1)(OC)OC ODZKSQBRXBCWSX-UHFFFAOYSA-N 0.000 description 1
- OLSQLFGIOFQZJG-UHFFFAOYSA-N CCCCCCCCCC(CC1CCCC1)(OCC)OCC Chemical compound CCCCCCCCCC(CC1CCCC1)(OCC)OCC OLSQLFGIOFQZJG-UHFFFAOYSA-N 0.000 description 1
- QFQUIPOQXPMPJP-UHFFFAOYSA-N CCCCCCCCCC(CCC1CCCC1)(OCC)OCC Chemical compound CCCCCCCCCC(CCC1CCCC1)(OCC)OCC QFQUIPOQXPMPJP-UHFFFAOYSA-N 0.000 description 1
- BTVGJNNMQNQKCL-UHFFFAOYSA-N CCCCCCCCCCCCCOC(CCCCCCCCC)C(C)C Chemical compound CCCCCCCCCCCCCOC(CCCCCCCCC)C(C)C BTVGJNNMQNQKCL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- BCZWPKDRLPGFFZ-UHFFFAOYSA-N azanylidynecerium Chemical compound [Ce]#N BCZWPKDRLPGFFZ-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical group BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical group BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- IFGISCVRDGYJFS-UHFFFAOYSA-N butyl(dimethyl)phosphanium chloride Chemical compound [Cl-].CCCC[PH+](C)C IFGISCVRDGYJFS-UHFFFAOYSA-N 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- NDTCXABJQNJPCF-UHFFFAOYSA-N chlorocyclopentane Chemical group ClC1CCCC1 NDTCXABJQNJPCF-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YMCPYIUQBXOFEE-UHFFFAOYSA-N cyclohexen-1-yl(2,2-diphenylethoxy)silane Chemical compound C1(=CCCCC1)[SiH2]OCC(C1=CC=CC=C1)C1=CC=CC=C1 YMCPYIUQBXOFEE-UHFFFAOYSA-N 0.000 description 1
- ARQPDLGOESLVLG-UHFFFAOYSA-N cyclohexen-1-yl-ethoxy-diethylsilane Chemical compound CCO[Si](CC)(CC)C1=CCCCC1 ARQPDLGOESLVLG-UHFFFAOYSA-N 0.000 description 1
- HKAKPQSNPQPGHV-UHFFFAOYSA-N cyclohexen-1-yl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C1=CCCCC1 HKAKPQSNPQPGHV-UHFFFAOYSA-N 0.000 description 1
- QCYNOMAXDPUXAP-UHFFFAOYSA-N cyclopenta-2,4-dien-1-ylbenzene Chemical compound C1=CC=CC1C1=CC=CC=C1 QCYNOMAXDPUXAP-UHFFFAOYSA-N 0.000 description 1
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical class C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- OYKIERKRPUDEIV-UHFFFAOYSA-N decane;hydrochloride Chemical compound Cl.CCCCCCCCCC OYKIERKRPUDEIV-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- UHMKISIRZFDJRU-UHFFFAOYSA-L diethyl-methyl-[2-(1,1,6-trimethylpiperidin-1-ium-2-carbonyl)oxyethyl]azanium;diiodide Chemical compound [I-].[I-].CC[N+](C)(CC)CCOC(=O)C1CCCC(C)[N+]1(C)C UHMKISIRZFDJRU-UHFFFAOYSA-L 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001941 electron spectroscopy Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical group IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical group ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WQIQNKQYEUMPBM-UHFFFAOYSA-N pentamethylcyclopentadiene Chemical compound CC1C(C)=C(C)C(C)=C1C WQIQNKQYEUMPBM-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/40—Oxides
- C23C16/401—Oxides containing silicon
-
- 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
- H01L21/02118—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 carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
-
- 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
- H01L21/02112—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
- H01L21/02164—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 being a silicon oxide, e.g. SiO2
-
- 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
-
- 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
- H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
- H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
- H01L21/02274—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition in the presence of a plasma [PECVD]
-
- 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
-
- 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
-
- 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
- H01L21/314—Inorganic layers
- H01L21/316—Inorganic layers composed of oxides or glassy oxides or oxide based glass
- H01L21/31604—Deposition from a gas or vapour
- H01L21/31608—Deposition of SiO2
- H01L21/31612—Deposition of SiO2 on a silicon body
-
- 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
- H01L21/314—Inorganic layers
- H01L21/316—Inorganic layers composed of oxides or glassy oxides or oxide based glass
- H01L21/31604—Deposition from a gas or vapour
- H01L21/31633—Deposition of carbon doped silicon oxide, e.g. SiOC
-
- 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
-
- 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
- H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
- H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Metallurgy (AREA)
- Inorganic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Materials Engineering (AREA)
- Plasma & Fusion (AREA)
- Chemical Vapour Deposition (AREA)
Description
1252232 (1) 玖、發明說明 【發明所屬之技術領域】 本發明係有關於用在邏輯UL S I之多層配線技術中的 低介電層間絕緣膜材料。尤以含電漿聚合用矽烷化合物之 絕緣膜材料,其製造方法及其用途。 【先前技術】 電子產業之積體電路領域的製造技術中,高積體化及 高速化之要求逐步提高。在矽ULSI,尤以邏輯ULSI中 MO SFET之微細化所需性能及相關配線性能已成課題。亦 即’隨多層配線之發展,爲解決配線延遲問題,有降低配 線電阻及降低配線間及層間電容之要求。 爲此,目前用於大多數積體電路之鋁配線必須改用電 阻更低,具有抗遷移性之銅配線,以濺鍍或化學蒸鍍(以 下簡稱CVD )法成膜後鍍銅之製程逐漸成熟。 低介電率層間絕緣膜有種種提議。習知技術係用無機 系之二氧化矽(Si02 )、氮化矽、磷矽酸玻璃,有機系之 聚醯亞胺。而最近爲得更均勻之層間絕緣膜,有使用將四 乙氧基矽烷單體水解,即聚縮合得S i 0 2之所謂旋塗玻璃 (無機SOG)的塗布材料之提議,及以有機烷氧基矽烷單 體聚縮合得聚矽氧烷用作有機SOG之提議。 又,絕緣膜形成方法則有,以絕緣膜聚合物溶液用旋 塗法等之塗布、成膜的塗布型,及主要係於電漿C VD裝 置中電漿聚合成膜之C VD法二種。 (2) (2)1252232 成膜方法之特徵,在電漿c V D法係,阻礙金屬與銅 配線材料之密合性良好,但膜之均勻性或有問題。塗布型 者雖膜之均勻性佳,但因須塗布、去除溶劑、去處理三過 程’比C VD材料不經濟,並且,阻礙金屬與銅配線材料 之密合性’塗布液的均勻塗布於微細化之基板結構時的塗 布本身常有問題。 塗布型材料,有爲實現電容率2.5以下,甚至於2 . 〇 以下之超低k材料而使用多孔性材的方法之提議。亦有, 以易於有機系或無機系材料基質中熱解之有機成分微粒分 散’熱處理之多孔化方法,使矽及氧於氣體中蒸發形成 Si〇2超微粒並蒸鍍,以形成Si〇2超微粒薄膜之方法等。 然而’此等多孔化方法雖有效降低介電常數,但機械 強度差難作化學機械硏磨(CMP ),又會吸水引起介電常 數上升及配線腐蝕。 因此’市場上更要求有介電常數低,機械強度足,能 滿足與阻礙金屬之密合性、抗銅擴散、耐電漿打磨性、耐 吸濕性等所有要求性能之均衡佳之材料。此等要求可達某 種程度平衡之方法者,已見有機矽烷系材料,該材料由於 提升對砂烷之有機取代基中碳原子比率而呈介於有機聚合 物及無機聚合物間的特徵者之提議。 例如專利文獻丨中提議,具金剛基之矽化合物在酸性 水溶液共存下’以溶膠凝膠法水解聚縮合用作塗布液,不 多孔化亦可得電容率2.4以下之層間絕緣膜的方法。然而 ,該材料係塗布型材料,依然有上述以塗布型材料成膜之 -8- (3) (3)1252232 問題。 又,專利文獻2係以三甲基矽烷、二甲基二甲氧基矽 院、一乙基一乙氧基砂院等及氧、氧化二氮、二氧化碳等 氧化劑原料,用P E C VD裝置氧化得氧化甲基矽烷膜。然 而’如後敘實施例,僅具一級短鏈烷基之矽烷,有 PECVD成膜速率不足,供低介電化之碳原子含量低之問 題。 專利文獻1 :日本專利特開2 0 0 0 — 3 0 2 7 9 1號公報 專利文獻2 ··特開2 0 0 2 — 1 1 〇 6 7 0號公報 【發明內容】 〔發明所欲解決之課題〕 本發明鑑於上述問題,其目的在提供,新穎低介電材 料’尤以含適於PECVD裝置之烷基矽烷材料之低介電絕 緣膜用材料,並提供使用彼之絕緣膜,以及含該等絕緣膜 之半導體裝置。 〔用以解決課題之手段〕 本發明人等發現,具至少有一個二級烴基及/或三級 烴基直接鍵結於矽原子之結構的有機矽烷化合物,適用作 絕緣膜’尤以半導體裝置用之低介電層間絕緣膜材料,終 於完成本發明。 亦即,本發明係在提供含下述一般式(i ) (4) 1252232
(式中R1、R2、R3表碳原子數1至20之烴基。R1、R2 、R3可互相結合形成環狀結構。R4表碳原子數1至1 〇 之烴基或氫原子,a表1至3之整數。) 所示之有機矽烷化合物, 下述一般式(2 )
(式中R5、R6表碳原子數1至20之烴基,R7、R8表氫 原子或碳原子數1至20之烴基。諸R5、或R6與R8 , 可互相結合形成環狀結構。b及c各表0或1。) 所示之有機矽烷化合物,或 下述一般式(3 )
(式中R9、R1G、R11表碳原子數1至20之烴基。R9、 R10亦可互相結合形成環狀結構。R12表碳原子數1至 10之烴基或氫原子。d表1至3之整數,e表0至2之整 數,d+e表3以下之整數。) -10- (5) (5)1252232 所示之有機矽烷化合物,以化學氣相成長法形成之絕緣膜 用材料。 以下詳細說明本發明。 上述一般式(1 )中,R1、R2、R3係碳原子數1至 2 0之飽和或不飽和烴基,可具直鏈、分枝、環狀之任一 結 構 〇 又, 其互 相結 合者亦包含在本發明範 圍 內 0 碳 原 子 數 超 過 20 時, 對應 之有機氯化物等原料難 以 取 得 即 可 取 得 純 度或 低。 考 慮在 PEC VD 裝置之安定使用時,有 機 石夕 院 化 合 物 之 〇 氣 壓不 宜過 低, 故以碳原子數1至10 之 烴 基 爲 尤 佳 R1 、R2 丨、R3 烴; 基之例無特殊限制,有碳原子數 1 至 2 0 較 佳者 爲碳 原子 數1至10之烷基、芳 基 > 芳 烷 基 、 院 基 芳 基。 R1、 R2、 r3可係相同或不同。 R1 、R: 2、R3 不 互相結合者之例有甲基 - 乙 基 Λ 正 丙 基 異 丙基 、正 丁基 、異丁基、二級丁基、 第 三 丁 基 、 正 戊 基 第三 戊基 、正 己基、環己基、苯基、 甲 苯 基 等 〇 R1 、R: 2、R3 互 相結合者之代表例有1 — 金 剛 基 〇 R1 > R2 、 R3 之組合係 Rl ' R2、R3均爲甲基 之 第 二 丁 基 , R1 Λ R2 :爲 甲基 R3 爲乙基之第三戊基,R 1 , R R 3 結 合 成 1 —金 剛基 ,乃 經濟上較佳之三級烴基 〇 R4 表i 碳原子數 1至10之烴基或氫原 子 , 烴 基 者 可 係 飽 和 或不 飽和 ,可 具直鏈、分枝、環狀之 任 — 結 構 〇 碳 原 子 數 超過 10 時, 其有機矽烷蒸氣壓低, 有 時 難 以 用 於 -11 - (6) 1252232 PEC VD裝置而不佳。 R4係以碳原子數1至4之烴基,;甲基、乙基、正丙 基、異丙基、正丁基、異丁基、二級丁基、第三丁基者原 料較易取得。 a表1至3之整數,亦即,a二1表烴基取代三烷氧基 矽烷類,a = 2表二經基取代二烷氧基矽烷,而a = 3表二 烴基取代烷氧基矽烷。此等之混合物亦包含於本發明之範 圍。 一般式(1 )所表之有機矽烷化合物,具體例有第三 丁基三甲氧基矽烷、二(第三丁基)二甲氧基矽烷、第三 戊基三甲氧基矽烷、二(第三戊基)二甲氧基矽烷、1-金剛基三甲氧基矽烷、二(1 -金剛基)二甲氧基矽烷、 第三丁基三乙氧基矽烷、二(第三丁基)二乙氧基矽烷、 第三戊基三乙氧基矽烷、二(第三戊基)二乙氧基矽烷、 1 一金剛基三乙氧基矽烷、二(1-金剛基)二乙氧基矽烷 、第三丁基三異丙氧基矽烷、二(第三丁基)二異丙氧基 矽烷、第三戊基三異丙氧基矽烷、二(第三戊基)二異丙 基矽烷、1 一金剛基三異丙基矽烷、二(1 一金剛基)二異 丙基矽烷、1-三環癸基三甲氧基矽烷、二(1-三環癸基 )二甲氧基矽烷、1一二膽鹼基二甲氧基矽烷、二(1 一二 膽鹼基)二甲氧基矽烷、1-三甲丁基三甲氧基矽烷、二 (1 一三甲丁基)二甲氧基矽烷等。 上述一般式(2 )中R5、R6係碳原子數1至2〇之飽 和或不飽和烴基,可具直鏈、分枝、環狀之任一結構。乂 -12- (7) 1252232 ,其互相結合者亦包含在本發明之範圍內。碳原子數超過 2〇時,其對應有機氯化物等原料難以取得,即可取得純 度亦或低。 考慮於CVD裝置之安定使用時,以碳原子數1至10 之烴基爲特佳。碳原子數超過1 0時,其有機矽烷之蒸氣 壓低,有時難以用於pECVD裝置而不佳。 R5、R6烴基之例無特殊限制,有碳原子數1至20, 較佳者爲碳原子數1至10之烷基、芳基、芳烷基、烷基 芳基。R5、R6可係相同或不同。 諸R5不結合者之例有甲基 '乙基、正丙基、異丙基 、正丁基、異丁基、二級丁基、第三丁基、正戊基、第三 戊基、正己基、環己基、苯基、甲苯基等。 諸R5互相結合者之代表例有1 -金剛基。 R7、R8表氫原子或與R5、R6同樣之烴基。亦可R6 與R8互相結合形成環狀結構,有如同上述諸R5互相結 合者之例。 b及c各表〇或1。亦即b=i,c二〇表烴基二取代二 院興基砂院’ b^o,c=0表煙基二取代院氧基砂焼,b二 〇 ’ c = 1表烴基六取代二矽氧烷。此等混合物亦含有本發 明之範圍。 一般式(2 )所表之有機矽烷化合物,具體例有 (A)第三丁基甲基二乙氧基矽烷、第三丁基甲基二 甲氧基矽烷、第三丁基甲基二羥基矽烷、第三丁基乙基二 乙氧基矽烷、第三丁基乙基二甲氧基矽烷、第三丁基乙基 -13- (8) 1252232 二羥基矽烷、第三丁基苯基二乙氧基矽烷、第三丁基苯基 二甲氧基矽烷、第三丁基苯基二羥基矽烷等, (B) 1 -金剛基甲基二乙氧基矽烷、1 一金剛基甲基 二甲氧基矽烷、1 -金剛基甲基二羥基矽烷、1 -金剛基乙 基二乙氧基矽烷、1 -金剛基乙基二甲氧基矽烷、1 -金剛 基乙基—> 經基砂院、1-金剛基本基—·乙氧基砂院、1-金 剛基苯基二甲氧基矽烷、1 -金剛基苯基二羥基矽烷等, (C )第三丁基二甲基羥基矽烷、第三丁基二甲基甲 氧基矽烷、第三丁基二甲基乙氧基矽烷、第三丁基二乙基 羥基矽烷、第三丁基二乙基甲氧基矽烷、第三丁基二乙基 乙氧基矽烷、第三丁基二苯基羥基矽烷、第三丁基二苯基 甲氧基矽烷、第三丁基二苯基乙氧基矽烷等, (D ) 1 -金剛基二甲基羥基矽烷、1 一金剛基二甲基 甲氧基矽烷、1-金剛基二甲基乙氧基矽烷、1一金剛基二 乙基羥基矽烷、1 -金剛基二乙基甲氧基矽烷、1 -金剛基 二乙基乙氧基矽烷、1-金剛基二苯基羥基矽烷、1-金剛 基二苯基甲氧基矽烷、1 -金剛基二苯基乙氧基矽烷等, (E) 1,3 —二(第三丁基)—1,1,3,3 —四甲基 二矽氧烷、1,3二(第三丁基)1,1,3,3 —四乙基二 矽氧烷、1,3二(第三丁基)1,1,3,3 —四苯基二矽 氧院等, (F) 1,3 —二(1—金剛基)1,1,3,3 —四甲基二 石夕氧院、1,3 — —. (1—金剛基)1,1,3,3 —四乙基一. 矽氧烷、1,3 —二(1 一金剛基)1,1,3,3 —四苯基二 -14- (9) 1252232 矽氧烷等。 上述一般式(3)中R9、R1Q、係碳原子數i至 20之飽和或不飽和烴基,可具直鏈、分枝、環狀任一結 構。又’其互相結合者亦含於本發明之範圍。碳原子數超 過2 0時’對應之有機氣化物等原料取得有困難,即能取 得有時純度亦低。 考慮於c v D裝置之安定使用時’有機矽烷化合物的 蒸氣壓不致過低,則以碳原子數1至10之烴基爲特佳。 R9 ^ R10 ' R1 1之烴基其例無特殊限制,有碳原子數 1至20,較佳者爲碳原子數1至10之院基、芳基、芳院 基、院基芳基。rIr^'r11可係相同或不同。 R9、R1G不互相結合之例有,甲基、乙基、正丙基、 異丙基、正丁基、異丁基、二級丁基、第三丁基、正戊基 、第三戊基、正己基、環己基、苯基、甲苯基等。 R9、R1 G互相結合,經二級碳原子與S i結合之基, 代表例有環丁基、環丁烯基、環戊基、環戊二烯基、環己 基、環己烯基、環辛烯基、環辛二烯基。其中 r9、r10 之組合經濟上較佳者有,R9、均係甲基之異丙基,R9 、R1Q 係甲基、乙基之二級丁基,R9、互相結合之環 戊基、%戊一;希基、環己基、環己烯基。 R12表碳原子數1至10之烴基或氫原子,烴基者係 飽和或不飽和烴基,可具直鏈、分枝、環狀之任一結構。 原子數超過1 0時,形成之有機砂院蒸氣壓低,有時難 以用於PEC VD裝置而不佳。 -15- (10) 1252232 R12以碳原子數l至4之烴基:甲基、乙基、正丙基 、異丙基、正丁基、異丁基、二級丁基、第三丁基、原料 取得上較佳。 d表1至3之整數,e表0至2之整數,d + e表3以 下之整數。亦即 d二1、e二0表烴基取代三烷氧基矽烷類 ,d=l、e= 1或d=2、e=0表烴基二取代二院氧基砂院 , (d=l、e=2)或(d=2、e二 1)或(d=3、e=0)表 烴基三取代烷氧基矽烷。其混合物亦含於本發明之範圍。 一般式(3 )所表之有機矽烷化合物,具體例有 (G) 異丙基三曱氧基矽烷、二異丙基甲氧基矽烷、 三異丙基甲氧基矽烷、異丙基甲基二甲氧基矽烷、異丙基 乙基二甲氧基矽烷、異丙基苯基二甲氧基矽烷、異丙基二 甲基甲氧基矽烷、異丙基二乙基甲氧基矽烷、異丙基二苯 基甲氧基矽烷, (H) 異丙基三乙氧基矽烷、二異丙基二乙氧基矽烷 、三異丙基乙氧基矽烷、異丙基甲基二乙氧基矽烷、異丙 基乙基二乙氧基矽烷、異丙基苯基二乙氧基矽烷、異丙基 二甲基乙氧基矽烷、異丙基二乙基乙氧基矽烷、異丙基二 苯基乙氧基矽烷, (I )二級丁基三甲氧基矽烷、二(二級丁基)二甲 氧基矽烷、三(二級丁基)甲氧基矽烷、二級丁基甲基二 甲氧基矽烷、二級丁基乙基二甲氧基矽烷、二級丁基苯基 二甲氧基矽烷、二級丁基二甲基甲氧基矽烷、二級丁基二 乙基甲氧基矽烷、二級丁基二苯基甲氧基矽烷, -16- (11) 1252232 (J)二級丁基三乙氧基矽烷、二(二級丁基)二乙氧 基矽烷、三(二級丁基)乙氧基矽烷、二級丁基甲基二乙 氧基矽烷、二級丁基乙基二乙氧基矽烷、二級丁基苯基二 乙氧基矽烷、二級丁基二甲基乙氧基矽烷、二級丁基二乙 基乙氧基矽烷、二級丁基二苯基乙氧基矽烷, (K) 環戊基三甲氧基矽烷、二環戊基二甲氧基矽烷 、三環戊基甲氧基矽烷、環戊基甲基二甲氧基矽烷、環戊 基乙基二甲氧基矽烷、環戊基苯基二甲氧基矽烷、環戊基 二甲基甲氧基矽烷、環戊基二乙基甲氧基矽烷、環戊基二 苯基甲氧基矽烷, (L) 環戊基三乙氧基矽烷、二環戊基二乙氧基矽烷 、三環戊基乙氧基矽烷、環戊基甲基二乙氧基矽烷、環戊 基乙基二乙氧基矽烷、環戊基苯基二乙氧基矽烷、環戊基 二甲基乙氧基矽烷、環戊基二乙基乙氧基矽烷、環戊基二 苯基乙氧基矽烷, (M) 環戊二烯基三甲氧基矽烷、二環戊二烯基二甲 氧基矽烷、三環戊二烯基甲氧基矽烷、環戊二烯基甲基二 甲氧基矽烷、環戊二烯基乙基二甲氧基矽烷、環戊二烯基 苯基二甲氧基矽烷、環戊二烯基二甲基甲氧基矽烷、環戊 二烯基二乙基甲氧基矽烷、環戊二烯基二苯基甲氧基矽烷 1 (N )環戊二烯基三乙氧基矽烷、二環戊二烯基二乙氧 基矽烷、三環戊二烯基乙氧基矽烷、環戊二烯基甲基二乙 氧基矽烷、環戊二烯基乙基二乙氧基矽烷、環戊二烯基苯 -17- (12) 1252232 基二乙氧基矽烷、環戊二烯基二甲基乙氧基矽烷、環戊二 烯基二乙基乙氧基矽烷、環戊二烯基二苯基乙氧基矽烷, (〇)環己基三甲氧基矽烷、二環己基二甲氧基矽烷 、三環己基甲氧基矽烷、環己基甲基二甲氧基矽烷、環己 基乙基二甲氧基矽烷、環己基苯基二甲氧基矽烷、環己基 二甲基甲氧基矽烷、環己基二乙基甲氧基矽烷、環己基二 苯基甲氧基矽烷, (P )環己基三乙氧基矽烷、二環己基二乙氧基矽烷 、三環己基乙氧基矽烷、環己基甲基二乙氧基矽烷、環己 基乙基二乙氧基矽烷、環己基苯基二乙氧基矽烷、環己基 二甲基乙氧基矽烷、環己基二乙基乙氧基矽烷、環己基二 苯基乙氧基矽烷, (Q) 環己烯基三甲氧基矽烷、二環己烯基二甲氧基 矽烷、三環己烯基甲氧基矽烷、環己烯基甲基二甲氧基矽 烷、環己烯基乙基二甲氧基矽烷、環己烯基苯基二甲氧基 矽烷、環己烯基二甲基甲氧基矽烷、環己烯基二乙基甲氧 基矽烷、環己烯基二苯基甲氧基矽烷、 (R) 環己烯基三乙氧基矽烷、二環己烯基二乙氧基 矽烷、三環己烯基乙氧基矽烷、環己烯基甲基二乙氧基矽 烷、環己烯基乙基二乙氧基矽烷、環己烯基苯基二乙氧基 矽烷、環己烯基二甲基乙氧基矽烷、環己烯基二乙基乙氧 基矽烷、環己烯基二苯基乙氧基矽烷等。 上述一般式(1 )之有機矽烷化合物之製造方法無特 殊限制,例如,可將下述一般式(4 ) -18- (13) 1252232 R2
R1—C—X R3 ( 4 ) (式中R1至R3同上。X表氯原子、溴原子、碘原子。 ) 所示之有機鹵化物,與金屬鋰粒子反應製造之三級碳原子 與鋰原子直接鍵結之有機鋰,與下述一般式(5 ) X,mSi ( OR4 ) 4- m ( 5 ) . (式中R4同上。X’表氟原子、氯原子、溴原子、碘原 子、m表0至3之整數。) 所示之鹵化烷氧基矽烷(m=l至3)或四烷氧基矽烷(m =〇)反應,製造一般式(1)之有機矽烷化合物。一般式 (4 )所表之有機鹵化物有例如,第三丁基氯、第三丁基 溴、第三丁基碘、第三戊基氯、第三戊基溴、第三戊基碘 、1 —金剛基氯、1 —金剛基溴、1 —金剛基碘、1 一三環癸 基氯、1 一三環癸基溴、1 一三環癸基碘、1 -二膽鹼基氯 、1 一二膽鹼基溴、1一二膽鹼基碘、1—三甲丁基氯、1一 三甲丁基溴、1-三甲丁基碘等。 一般式(5)所表之鹵化烷氧基矽烷或四烷氧基矽烷 有例如,氯化三甲氧基矽烷、二氯二甲氧基矽烷、三氯甲 氧基矽烷、四甲氧基矽烷、氯化三乙氧基矽烷、二氯二乙 氧基矽烷、三氯乙氧基矽烷、四甲氧基矽烷、四乙氧基矽 烷、四丙氧基矽烷、氯化三異丙氧基矽烷、二氯二異丙氧 基矽烷、三氯異丙氧基矽烷、四異丙氧基矽烷、四丁氧基 -19- (14) 1252232 矽烷、四異丁氧基矽烷、四(二級丁氧基)矽烷、四(三 級丁氧基)矽烷等。 ί木用本製造方法可抑制副產物之生成,得高收率、高 純度之一般式(1 )之有機矽烷化合物。尤以使用有機鎂 等之其它製造方法,可製造出工業上難以製造之有二以上 二級碳原子直接鍵結於矽原子之結構的有機矽烷化合物。 上述一般式(5)之有機鹵化物與金屬鋰粒子之反應 條件無特殊限制,以下即其一例。__________ 所用亞屬鋰’可係鋰絲、鋰帶、鋰九等,反應效率 上,以用粒徑5 0 0微米以下之鋰微粒爲佳。 用於有機鹵化物與金屬鋰粒子的反應之溶劑,若係該 技術領域所用者即無特殊限制,可用例如,正戊烷、異戊 烷、正己烷、環己烷、正庚烷、正癸烷等飽和烴類,甲苯 、二甲苯、癸烯一 1等不飽和烴類,二乙醚、丙醚、二丁 醚等醚類。 有機鹵化物與金屬鋰粒子之反應溫度,以生成之三級 碳原子與鋰直接鍵結之有機鋰不分解之溫度範圍爲佳。通 常,工業上之溫度在—100至200 °c之範圍,—85至150 °C較佳。反應壓力條件可係加壓、常壓、減壓之任一。 合成之三級碳原子與鋰原子直接鍵結之有機鋰,可能 製造後直接使用,亦可去除未反應之有機鹵化物、金屬鋰 及反應副產物鹵化鋰後使用。 三級碳原子與鋰原子直接鍵結之有機鋰,與上述一般 式(3 )之鹵化烷氧基矽烷或四烷氧基矽烷之反應條件無 -20- (15) 1252232 特殊限制,以下即其一例。 可用之反應溶劑有,如同上述有機鹵化物與金屬鋰粒 子反應時所用之溶劑。反應溫度較佳者爲,所用之三級碳 原子與鋰直接鍵結的有機鋰不分解之溫度範圍。通常,工 業上所用溫度在—1〇〇至200 °c之範圍,—85至150°C爲 較佳。反應之壓力條件,可係加壓、常壓、減壓之任一。 上述一般式(2 )之有機矽烷之製造方法無特殊限制 ,例如,可使上述一般式(2 )中b二1且c二0的下述一 般式(9 )之烴基二取代二烷氧基矽烷 R5 R5 R5-C——Si——OR8 Η R7 (9) (式中,R5、R7、R8同上述一般式(2)。) 或b=0且c=0的下述一般式(10)之烴基三取代院氧基 矽烷, R5 R5 5丨丨B R5-C——Si——OR8
(式中,R5、R7、R8同上述一般式(2 )。) 與下述一般式(1 1 )之有機鋰化合物或有機鎂化合物 R5 R5 - C一Μ (11) -21 - (16) 1252232 (式中R5同上述一般式(2 ) 。μ表Li、MgCl、MgBr、
Mg1 ° )及下述一般式(i 2 )之烴基取代鹵化矽烷或烴基 耳又代院氧基砂院
ZfSiR^j ( 〇 ) bR7]h ( 〇R8 4_ (f + g + h) (12) (式中,R5、R7、R8、b同上述一般式(2 ) 。Z表氟原子 、氯原子、溴原子或碘原子。f係〇至3之整數,g係〇 至2之整數’ 11係13=0時〇至2之整數,b=i時〇至4 之整數,f + g + h係〇至4。) 反應而製造。 上述一般式(2)中c=i之烴基六取代二矽氧烷,其 製造方法無特殊限制,可將所得烴基二取代二烷氧基矽烷 或煙基三取代烷氧基矽烷在水及酸之共存下,二聚化而製 造° 更於合成反應後’當產物烴基取代烷氧基矽烷中殘留 有直接鍵結於矽原子之鹵素原子時,可用下述一般式(;[3 ) R8OM· (13) (式中M’係鹼金屬,r8同上述一般式(2)。)之鹼金 屬烷氧化物反應而烷氧化。 上述一般式(1 3 )所表之鹼金屬烷氧化物,有例如甲 醇鋰、乙醇鋰、異丙醇鋰、甲醇鈉、乙醇鈉、異丙醇鈉、 甲醇鉀、乙醇鉀、異丙醇鉀等。· 採用本製造方法可抑制副產物之生成,得高收率高純 度之一般式(1 )所示有機矽烷化合物。 -22- (17) (17)1252232 用於製造時之上述一般式(11 )的有機鋰化合物或有 機鎂化合物,可使有機鹵化物與金屬鋰粒子或金屬鎂反應 而製造。 上述一般式(1 1 )之有機鋰化合物或有機鎂化合物, 合成時有機鹵化物與金屬鋰粒子或金屬鎂之反應條件無特 殊限制,以下即其一例。 所用之金屬鋰,可係鋰絲、鋰帶、鋰九等,於反應效 率上,係以粒徑5 0 0微米以下之鋰微粒爲佳。 所用之金屬鎂,可係鎂帶、鎂粒子、鎂粉等。 用於上述反應之溶劑,若係該技術領域所用者即無特 殊限制,可用例如正戊烷、異戊烷、正己烷、環己烷、正 庚烷、正癸烷等飽和烴類,甲苯、二甲苯、癸烯- 1等不 飽和烴類,二乙醚、二丙醚、第三丁基甲醚、二丁基醚、 環戊基甲醚等醚類。又,可使用此等之混合溶劑。 上述反應之反應溫度較佳者在,生成之有機鋰或有機 鎂不分解之範圍。通常工業上係用—100至2〇0°C之範圍 ,-8 5至1 5 0°c較佳。反應之壓力條件可係加壓、常壓、 減壓之任一。 合成之有機鋰或有機鎂可於調製後直接使用,亦可$ 除未反應之有機鹵化物,金屬鋰、金屬鎂及反應副產之鋰 鹵化物、鎂鹵化物後使用。 有機鋰或有機鎂與上述一般式(1 2 )之烴基取代國化 砂烷或烴基取代烷氧基矽烷之反應條件無特殊限制,以下 即其一例。 -23- (18) 1252232 可用之反應溶劑有,如同上述有機鹵化物與金屬鋰或 金屬鎂反應時所用之溶劑。反應溫度較佳者爲’所用之有 機鋰或有機鎂不分解之溫度範圍。通常工業用之溫度在 —1 〇 0至2 0 0 °c之範圍,—8 5至1 5 0 °c更佳。反應壓力條 件可係加壓、常壓、減壓之任一。 殘留有直接鍵結於矽原子之鹵素原子時與上述一般式 (1 3 )之鹼金屬烷氧化物之反應條件無特殊限制,可用如 同上述有機鋰或有機鎂與鹵化烷氧基矽烷或四烷氧基矽烷 反應之條件。 上述一般式(3 )之有機矽烷化合物之製造方法無特 殊限制,例如,可使下述一般式(6 ) R9
I
HC—Y R10 (6) (式中r9、r1g同上。Y表氫原子、氯原子、溴原子、 碘原子。) 所示之有機化合物,與有機鋰或金屬鋰粒子反應,製成二 級碳原子與鋰原子直接鍵結之化合物,其與下述一般式( 7) Y'pSiRllq ( OR12) 4- (p+ q) ( 7 } (式中Y’表氟原子、氯原子、溴原子或碘原子,rU、r12 同上。P表〇至4之整數,q表〇至2之整數,{}+9表4 以下之整數。) 所示之鹵化矽烷、鹵化烷氧基矽烷或四烷氧基砍院反應, -24- (19) 1252232 製造一般式(3 )所表之有機矽烷化合物。 又’上述製造方法中,取代有機鋰或金屬鋰粒子,改 用金屬鎂’製造一般式(3 )之有機矽烷化合物的方法, 亦在本發明之範圍內。 一般式(6 )所表之有機化合物中,Y係氯原子、溴 原子或碘原子之例,有異丙基氯、異丙基溴、異丙基碘、 二級丁基氯、二級丁基溴、二級丁基碘、環戊基氯、環戊 基溴、运戊基碘-、環己基氯、環己基溴、環己基碘。 又’ 一般式(6 )所表之有機化合物中,Y係氫原子 之例有環戊二烯、五甲基環戊二烯、1,2,3,4 一四甲基 - 1,3 —環戊二烯等,此等化合物以正丁基鋰、第三丁基 鋰等有機鋰反應,即可製造二級碳原子與鋰原子直接鍵結 之化合物。 一般式(7)之鹵化矽烷、鹵化烷氧基矽烷或四烷氧 基矽烷之例有四氯矽烷、氯化三甲氧基矽烷、二氯二甲氧 基矽烷、三氯甲氧基矽烷、四甲氧基矽烷、氯化三乙氧基 矽烷、二氯二乙氧基矽烷、三氯乙氧基矽烷、四乙氧基矽 烷、四丙氧基矽烷、氯化三異丙氧基矽烷、二氯二異丙氧 基矽烷、三氯異丙氧基矽烷、四異丙氧基矽烷、四丁氧基 矽烷、四異丁氧基矽烷、四(二級丁氧基)矽烷、四(三 級丁氧基)矽烷、甲基三甲氧基矽烷、二甲基二甲氧基矽 烷、乙基三甲氧基矽烷、二乙基二乙氧基矽烷、乙烯基三 乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三氯矽烷、二 乙烯基二氯矽烷、苯基三甲氧基矽烷、二苯基二甲氧基矽 -25- (20) 1252232 烷等。 又’合成反應後,產物烴基取代烷氧基矽烷中殘留有 1:接鍵結於矽原子之鹵素原子時,可與下述一般式(8 ) R12〇M ( 8 ) (式中Μ係鹼金屬,同上。) 所示之驗金屬烷氧化物反應而烷氧基化。 一般式(8 )所表之鹼金屬烷氧化物有例如,甲醇鋰 、乙醇鋰、異丙醇鋰、甲醇鈉、乙醇鈉、異丙―醇鈉、甲醇 鉀、乙醇鉀、乙醇鉀、異丙醇鉀等。 採用本製造方法可抑制副產物之生成,可得高收率、 商純度之一般式(3 )之有機政院化合物。 二級碳原子與鋰原子(或鎂原子)直接鍵結之化合物 ,其製造條件無特殊限制,以下即其一例。 所用之金屬鋰,可係鋰絲、鋰帶、鋰九等,反應效率 上係以粒徑5 00微米以下之鋰微粒爲佳。 所用金屬鎂,可係鎂帶、鎂粒子、鎂粉等。 所用有機鋰,可係正丁基鋰之正己烷溶液,第三丁基 鋰之正庚烷溶液等。 用於上述反應之溶劑,若係該技術領域所用者即無 特殊限制,可用例如正戊烷、異戊烷、正己烷、環己烷、 正庚烷、正癸烷等飽和烴類,甲苯、二甲苯、癸烯一 1等 不飽和烴類,二乙醚、二丙醚、第三丁基甲醚、二丁基醚 、環戊基甲醚等醚類。又,亦可使用此等之混合溶劑。 上述反應之反應溫度較佳者爲,生成之二級碳原子與 -26- (21) 1252232 鋰原子結合之化合物,或二級碳原子與鎂原子直接鍵結之 化合物不分解之溫度範圍。通常,工業上所用溫度係 —100至200 °C之範圍,—85至150 °c更佳。反應之壓力 條件可係加壓、常壓、減壓之任一。 合成之二級碳原子與鋰原子直接鍵結之化合物,或二 級碳原子與鎂原子直接鍵結之化合物,可於製造後直接使 用,亦可去除未反應之有機鹵化物、金屬鋰、金屬鎂、反 應副產之鋰鹵化物、鎂鹵化-物後使用。 ------- 如此而得之二級碳原子與鋰原子直接鍵結之化合物, 或二級碳原子與鎂原子直接鍵結之化合物,與上述一般式 (3)之鹵化矽烷、鹵化烷氧基矽烷或四烷氧基矽烷之反 應條件無特殊限制,以下即其一例。 可用之反應溶劑有,如同上述二級碳原子與鋰原子( 或鎂原子)直接鍵結之化合物的反應時可用之溶劑。反應 溫度較佳者係,在二級碳原子與鋰原子(或鎂原子)直接 鍵結之化合物不分解之範圍。通常工業上所用者爲一 1 00 至2 00 °c之範圍,—85至150°C更佳。反應之壓力條件可 係加壓、常壓、減壓之任一。 生成之一般式(1 )至(3 )之有機矽烷化合物,其純 化方法係’爲使可用作絕緣膜材料之水分含量不及 5 0 ppm ’矽、碳、氧、氫以外之來自製造原料之雜質元素量 不及1 〇 ppb ’可將副產之鋰鹽、鎂鹽、鹼金屬鹽用玻璃濾 材、燒結多孔體等過濾,以常壓或減壓蒸餾,或使用氧化 石夕' 氧化鋁、高分子凝膠之管柱分離純化等手段去除。此 -27- (22) 1252232 時’若必要可組合以上手段使用。如用於一般有機合成技 術’將副產之鋰鹽、鎂鹽、鹼金屬鹽以水等萃取之方法, 最終所得之一般式(1 )之有機矽烷化合物中,水分、矽 '碳、氧、氫以外元素雜質,尤以金屬雜質殘留量高,有 時不適作絕緣膜材料。
又,含具矽烷醇結構之副產物時,可將矽烷醇之羥基 以氫氧化鈉或氫氧化鉀等形成鈉鹽或鋰鹽沈澱後,蒸餾分 離出主要產物烴基取代烷氧基矽烷。 _ 製造時係依該有機金屬化合物合成領域中之方法。亦 即’較佳者爲,於脫水、脫氧之氮或氬氣環境下進行,所 用之溶劑及純化用管柱塡料等,預先施行脫水操作。又, 以先:去除金屬殘渣及顆粒等雜質爲佳。 本發明之一般式(1 )至(3 )之有機矽烷化合物,係 適用作以PECVD裝置成膜爲低介電絕緣材料之原料。
此等材料以 CVD成膜後,於切斷三級碳原子與矽原 子之3 5 0°C以上之溫度作熱處理,向膜外釋出烴分子以圖 形成分子大小孔洞而多孔化,亦可降低介電率,得低介電 絕緣材料。 本發明之低介電絕緣材料,適於採用多層配線之 ULSI之製造,設置該絕緣膜而成之半導體裝置亦含於本 發明之權利範圍。 【貫施方式】 〔實施例〕 -28- (23) 1252232 以下提示實施例,惟本發明絕非僅限於此等實施例。 實施例1 〔三級碳原子與鋰原子直接鍵結之有機鋰的製造〕
氮氣流下,於配備滴液漏斗之2 〇 〇毫升施嫩克管反應 器饋入平均粒徑150微米之Li粒子1.40克(0.200毫升 )及乾燥戊烷100毫升,於30°C —面攪拌一面經滴液漏 斗滴下,以保持1 -溴金剛院21.5克(0。100莫耳)镕解 於正戊烷5 0毫升之溶液內溫於3 〇°C,再於正戊烷之回流 條件下攪拌1 4小時。 反應完後濾除未反應之金屬Li及副產物LiBr,得1 -金剛基鋰之正戊烷溶液。 〔三級碳原子直接鍵結於矽原子之有機矽烷化合物的製造 )
於配備滴液漏斗之2 0 0毫升施嫩克管反應器饋入乾燥 戊烷50毫升,及四甲氧基矽烷13.7克(〇.〇 90莫耳), 如上述製造之1 -金剛基鋰於正戊烷之溶液經滴液漏斗滴 下,並保持內溫於0 °C。滴完後於室溫攪拌2小時。反應 完後,餾去正戊烷,以管柱層析分離純化目標產物1 -金 剛基三甲氧基矽烷。結果收率爲8 2 %。 實施例2 實施例1中,四甲氧基矽烷使用量,由1 3.7克( -29- (24) 1252232 ,如同竇施 甲執基砂院 0.090莫耳)改爲6·85克(0.045莫耳)以外 例1作實驗,得目標產物二(1 一金剛基)二 ,收率7 1 %。 比較例1 〔三級碳原子與鎂原子直接鍵結之有機鎂之製造〕 氮氣環境下,於配備回流冷却器、滴液漏斗、擾丨半裝 置之1,000毫升燒瓶,饋入鎂21.4克( 0.8 80莫—耳)及二 丁醚125.0克(0.960莫耳),開始攪拌後,將之由滴液 漏斗以2小時滴下,維持1 —溴金剛烷1 72. 1克(〇 8〇〇 莫耳)及乙基溴4.36克(0.0400莫耳)以二丁醚25〇〇 克(1 . 92莫耳)稀釋之溶液於二丁醚回流條件下,繼之於 同回流條件下攪拌4小時,得1 -金剛基溴化鎂之二丁 g迷 溶液。 〔三級碳原子直接鍵結於矽原子之有機矽烷化合物的製造 ) 氮氣環境下,於配備回流冷却器、攪拌裝置之2,000 毫升反應器饋入乾燥二丁醚200毫升及四甲氧基矽烷54.8 克(0.360莫耳)以回轉泵滴入加上述製造之1 一金剛基 溴化鎂之二丁醚溶液,並保持內溫於〇°C。滴完後於室溫 攪拌2小時。 以氣相層析確認產物,則生成目標產物二(1 -金剛 基)二甲氧基矽烷得以確認。再於二丁醚回流下攪拌2小 -30- (25) 1252232 時,確認生成二(1 一金剛基)二甲氧基矽烷。 實施例3 〔三級碳原子直接鍵結於鋰原子之有機鋰的製造j
氬氣流下,於配備回流冷却器、滴液漏斗之200毫升 施嫩克管反應器饋入平均粒徑75微米之Li粒子1.39克 (0.200莫耳)及乾燥戊烷50毫升,一面於3(rc攪拌, 一面由滴液漏斗滴下1 -氯金剛烷3.4 1克(〇 . 〇 2 〇莫耳) 溶解於正戊院5 〇莫耳之溶液保持內溫於3 0 °C。再於正戊 院之回流條件下攪拌8小時後,確認已無原料1 一氯金剛 烷之檢測,成1 -金剛基鋰之正戊烷溶液。 〔三級碳原子直接鍵結於矽原子之有機矽烷化合物的製造
氬氣環境下’於配備回流冷却器及滴液漏斗之200毫 升施嫩克管反應器饋入正戊烷50毫升及四乙氧基矽烷 3 . 3 3克(0.0 1 6莫耳),由滴液漏斗於室溫滴入如上述製 造之1 -金剛基鋰之正戊烷溶液。滴完後於正戊烷回流條 件下攪拌5小時。反應完後餾去正戊烷,以管柱層析分離 純化目標產物1 -金剛基二乙氧基砂院,收率72%。 實施例4 實施例3中,取代四乙氧基矽烷,改用四甲氧基矽烷 2.4 4 ( 0.0 1 6莫耳)以外,如同實施例3作實驗,得目標 -31 - (26) 1252232 產物[—金剛基二甲氧基砂院,收率7 8 %。 比較例2 (;三級碳原子與鎂原子直接鍵結之有機鎂的製造〕
氮氣環境下,於配備回流冷却器、滴液漏斗、攪拌裝 置之2〇〇毫升施嫩克管饋入鎂2.92克(〇.12〇莫耳)及二 丁醚3 0毫升,經滴液漏斗於8 0 °C以1小時滴入1 -溴金 剛烷21.5克( 0.100莫耳)及乙基溴1.-09克(〇.01 00莫 耳)溶解於二丁醚40毫升之溶液,再於120 °C攪拌2小 時,得1 -金剛基溴化鎂之二丁醚溶液。 〔三級碳原子直接鍵結於矽原子之有機矽烷化合物的製造 )
於上述200毫升施嫩克管中之1 一金剛基溴化鎂的二 丁醚溶液,由滴液漏斗於4 5 °C以1 〇分鐘滴入四乙氧基矽 烷16.7克(0·080莫耳)溶解於乾燥二丁醚20毫升之溶 液。滴完後於120 °C攪拌6小時。 以氣相層析一質譜分析裝置(GC - M S )分析反應液 ,完全確認1 一金剛基三乙氧基矽烷及二(1 一金剛基) 二乙氧基矽烷之生成。 實施例5 〔三級碳原子直接鍵結於矽原子之有機矽烷化合物的製造 -32- (27) 1252232 氮氣環境下’於配備回流冷却器、滴液漏斗、攪拌裝 置之5 0 0毫升四口燒瓶反應器饋入四乙氧基矽烷5 0.0克 (0.240莫耳)及正戊烷250莫耳,冷却至0°C。由滴液 漏斗於1小時滴入2 3 . 7重量%第三丁基鋰之正戊烷溶液 78.0克(0.289莫耳)’再攪拌2小時。 根據氣相層析內部標準法’第三丁基三乙氧基矽烷之 收率爲9 3.0 %。 從反應液濾除乙醇鋰,從濾液餾去正戊院後,減壓蒸 餾離析出第三丁基三乙氧基矽烷。收量39.6克,離析收 率 74.8%。 離析之第三丁基三乙氧基矽烷以1Η — NMR、13C — NMR、GC — MS分析,結果如下,呈示係高純度目標產物 〇 1H-NMR(CDC13) δ : 1.02 5 ppm ( s,9H ), l_285 ppm(t,9H) ,3.915 ppm(q,6H) 13C - NMR ( CDC 1 3 ) :17.583 ppm,18.426 ppm, 26.3 9 1 ppm,5 8.7 8 5 ppm GC— MS : Mw= 220,C10H24〇3Si 又’所得第三丁基三乙氧基矽烷100克中之水分及鋰 含量’以卡爾〜費歇水分計及ic P - MS (高頻電漿發光質 譜分析儀,橫河ANALYTICAL SYSTEMS公司製,商品名 “HP 4 5 00”)測定,結果 h2〇 二 17 ppm,Li < 10 ppb,適 用作絕緣膜材料 -33- (28) 1252232 比較例3 〔具三級碳原子直接鍵結於砂原子之結構的有機;^院丨匕合 物之製造〕 氮氣環境下,於配備回流冷却器、滴液漏斗、攪拌裝 置之500毫升四口燒瓶反應器饋入四乙氧基矽烷η·8克 (0.0567莫耳)及四氫呋喃50毫升,冷却至〇它。由滴 液漏斗以1小時滴入1.70莫耳/公升之第三丁基氯化鎂 的四氫呋喃溶液-4 0 -毫升(0.0 6 8 0莫琢),再攪拌2小時 。採取部份反應液,以氣相層析分析,無法確認第三丁基 三乙氧基矽烷之生成。 更於室溫攪拌3小時,反應後仍無法確認第三丁基三 乙氧基矽烷之生成。 再於四氫呋喃回流條件下攪拌3小時進行反應。依氣 相層析內部標準法,第三丁基三乙氧基矽烷之收率爲1.4 % ’知第三丁基氯化鎂與四乙氧基矽烷之反應,無法有效 合成目標產物。 實施例6 〔具三級碳原子直接鍵結於矽原子之結構的有機矽烷化合 物之製造〕 實施例5中,取代四乙氧基矽烷,改用四甲氧基矽烷 3 6.6克(0.2 40莫耳)以外,如同實施例5作實驗,得目 標產物第三丁基三甲氧基矽烷。依氣相層析內部標準法’ 第三丁基三甲氧基矽烷之收率爲9 1 . 1 %,減_蒸餾之離析 -34- (29) 1252232 收率爲7 Ο . Ο %。 度之 離析Ζ第二丁基二甲氧基砂院,以ιΗ— nmR、 13C — NMR、GC - MS分析’結果如下,呈示係高純 目標產物。 lH-NMR(CDCl3) 5 : 1.043 ppm ( s ^ 9H ) ^ 3.683 ppm (s,9 Η ) l3C - NMR ( CDC13 ) : 17.876 ppm , 26.410 ppm 5 1.2 77 ppm — GC — MS: Mw=178,C7Hi8〇3Si 量, =14 又,所得第三丁基三甲氧基矽烷中之水分及鋰含 以卡爾—費歇水分計及ICP — MS測定,結果爲h20 ppm,Li < 1 0 ppb ’適用作絕緣膜材料。 實施例7 純化 3作 74.0 標產 實施例3中’取代管柱層析,改以減壓蒸餾分離 目標產物1 -金剛基三乙氧基矽烷以外,如同實施例 實驗,得目標產物1 -金剛基三乙氧基矽烷,收率爲 %。 離析之1 一金剛基三乙氧基矽烷以1Η - NMR、 13 C — N M R、G C — M S分析,結果如下,係局純度目 物。 : 1.290 ppm ( t,9Η), 1.836 ppm 及 1.1886 pprn(d,15H), 3.890 ppm(q,6H) -35- (30) 1252232 l3C - NMR ( CDC 13 ) : 18.499 ppm,22.656 ppm, 2 7.453 ppm,36.975 ppm,37.616 ppm,5 8.78 5 ppm GC〜MS : Mw = 298,Ci6H30〇3Si 又’所得1 -金剛基三乙氧基矽烷中之水分及鋰含量 以卡爾—費歇水分計及ICP — MS測定,結果H20 = 10 p p m,L i < 1 〇 p p b,適用作絕緣膜材料。 實施例8 _ 一 〔第三丁基三甲氧基矽烷之電漿聚合成膜〕 薄膜之製作係用如第1圖之高頻感應耦合型遠距式電 漿CVD裝置(PECVD裝置)。本裝置之主要結構包括石 英玻璃製電漿源1、成膜室2、氣化器3、真空排氣裝置4 、矽基板5、高頻電源6及匹配網路7,於成膜室2具備 如第2圖之高靈敏度紅外反射吸收分光裝置(IRRAS )。 該IR R A S係將紅外線8以偏振片9偏振後,對沈積於石夕 基板5上之聚合膜以80度之入射角照射,來自聚合膜之 反應光以水銀•鎘•碲半導體紅外線傳感器檢測出,用以 確認聚合膜之成膜狀態。使用該裝置,如下作實施例6中 製造之第三丁基三甲氧基矽烷之電漿聚合成膜。 真空排氣成膜室2至1 4帕以下後,導入5標準立 方公分/分鐘之氧氣,以銳孔閥調整排氣速率,使成膜室 內壓力達1 〇帕。然後排出氧氣,經氣化器3導入原料第 Ξ 丁基三甲氧基矽烷氣體於成膜室2至內壓達10帕。內 壓安定後,於電漿源1施加7 5瓦之高頻產生電漿,於設 -36- (31) 1252232 置在成膜室2內之矽基板5上沈積薄膜。其間第三丁基三 甲氧基氣體之流量係維持在5標準立方公分/分鐘,成膜 1 2分鐘。 成膜中以IRRAS觀測,確認已沈積有具第三丁基直 接鍵結於矽原子之結構的氧化矽之聚合物。 所得矽基板上之電漿聚合薄膜,以電子顯微鏡(S E Μ )、X -射線電子分光裝置(XP S )、紅外線吸收分光裝 置(IR )分析,結果如下。 •膜厚(SEM) : 120奈米 •膜組成(XPS) :C=37原子%,〇=49原子%, S i = 1 4原子% • C/ Si - 2.64 •紅外線吸收(IR ):直接鍵結於矽原子之第三丁基 (2 95 6 cm— 1、1 479 cm一 1、72 7 cm — 1 ),直接鍵結於矽原 子之甲基( 2853 cm-1、1273 cm—、798 cm-1) 比較例4 〔甲基三甲氧基矽烷之電漿聚合成膜〕 實施例8中取代第三丁基三甲氧基矽烷,改用甲基三 甲氧基矽烷,聚合成膜時間改爲20分鐘以外,如同實施 例8於矽基板上形成電漿聚合薄膜,其分析結果如下。 • IRR AS :確認具有甲基直接鍵結於矽原子之結構的 氧化矽聚合物之沈積。 •膜厚(SEM ) : 22奈米 -37- (32) 1252232 •膜組成(XP S ) : c = 3 7原子%,Ο = 4 3原子%, S i = 2 0原子% • C/ Si 二 1 . 85 •紅外線吸收(IR ):直接鍵結於矽原子之甲基( 2 8 5 3 cm— 1、1 273 cm — 1、7 9 8 cm — 1 ),直接鍵結於矽原子 之氫(23 00 cm— 1附近寬峰),直接鍵結於矽原子之羥基 (3 3 0 0 c m — 1附近寬峰) 相較於實施调8,成膜速率慢-,碳組成量低,確認係-不適作絕緣膜之具有直接鍵結於矽原子的羥基及氫之聚合 物薄膜。 如上可知,僅以第三丁基三甲氧基矽烷作電漿聚合, 可在高於以往的成膜速率得適用作絕緣膜之於矽原子直接 鍵結有第三丁基以及甲基之高含碳量氧化砂聚合物薄膜。 實施例9 〔第三丁基二甲基氯化矽烷之合成〕 氮氣環境下,於配備回流冷却器、滴液漏斗、攪拌裝 置之3公升四口燒瓶反應器饋入二甲基二氯砂院258.2克 (2.00莫耳)及正戊烷600毫升,冷却至〇它。由滴液漏 斗以1小時滴入23.7重量%第三丁基鋰之正戊烷溶液 5 3 9.6克(2.0 0莫耳),再攪拌2小時。 反應後,濾除副產之氯化鋰,從濾液餾去正戊烷,蒸 餾離析出純化第三丁基二甲基氯化矽烷。收量2 3 5 . 1克, 離析收率7 8.0 % -38- (33) 1252232 〔第三丁基二甲基乙氧基矽烷之合成〕 氮氣流下,於配備攪拌裝置之2公升分離式燒瓶反應 器饋入第三丁基二甲基氯化矽烷156.9克(1.04莫耳), 純度9 6 %之乙醇鈉8 2.3克(1 . 1 6莫耳)及正己烷1.6公 升,在正己烷回流條件下反應2 2小時。 以玻璃濾材濾除固態殘渣,得反應混合物溶液。以氣 相層析分析,則目標產物第三丁基二甲基乙氧基矽烷之收 率爲 66.8 %,畐I]產物第三丁基二甲基羥基矽烷之收率 3 3.2%。 〔副產物之去除及第三丁基二甲基乙氧基矽烷之純化〕 氮氣流下,於配備攪拌裝置之2公升分離式燒瓶反應 器饋入上述反應混合物,加入氫化鈉16.6克(0.691莫耳 ),於室溫攪拌1小時。以氣相層析分析,則副產物第三 丁基二甲基羥基矽烷低於檢測下限。 反應完後以玻璃濾材濾除固態殘渣,得反應混合物溶 液。從反應混合物溶液餾去正己烷,以常壓蒸餾離析出目 標產物第三丁基二甲基乙氧基矽烷。 收量爲91.5克(0.572莫耳),相當於收率55.0%。 離析之第三丁基二甲基乙氧基矽烷以1Η - NMR、 13C — NMR、GC — MS分析,結果如下。 ^-NMR : 0.0 79 ppm ( s,6H ), 1.01 ppm(s,9H ) 1.13 ppm ( t ^ 3 H ), 3.56 ppm (q,2 H ) -39- (34) 1252232 13C— NMR : 18.23 ppm,18.66 ppm,2 5.92 ppm, 5 8.51 ppm GC - MS ·· Mw 二 160 ’ C8H2〇OSi 又,所得第三丁基二甲基乙氧基砂院100克中之水分 量及鈉、鋰含量以卡爾-費歇水分計及ICP - MS (高頻電 漿發光—質譜分析儀,橫河ANALYTICAL SYSTEMS公司 製,商品名“HP 45 00”)測定,結果h20= 10 ppm,Na< 1 0 - p p p,- L i < 1 0 p p b,適用-作絕緣膜材料。 — 比較例5 實施例9中,第三丁基二甲基氯化矽烷與乙醇鈉反應 後,不濾除氯化鈉及未反應之乙醇鈉,加水萃取去除可溶 分’更以氫化鈉與副產物第三丁基二甲基羥基矽烷反應加 以去除,此外如同實施例1調製二級丁基二甲基乙氧基矽 院。 所得第三丁基二曱基乙氧基矽烷中之水分及鈉含量, 以卡爾—費歇水分計及ICP — MS測定,則h2〇= 210 ppm ,N a = 9 8 p p m,不適作絕緣膜材料。 實施例1 〇 〔—級碳原子直接鍵結於鋰原子之有機鋰的製造〕 氮氣流下,於配備滴液漏斗、攪拌裝置之2〇〇毫升施 嫩克管反應器饋入雙環戊二烯裂解蒸餾所得之環戊二烯 1 5 ‘ 8克(2 3 9毫旲耳)及乾燥四氫呋喃$ 〇毫升,冷却至 -40- (35) 1252232 一 2 0 °C,攪拌下以4 5分鐘滴入2.6 6莫耳/公升之正丁基 鋰9 0.0毫升(23 9毫莫耳),於—20 °C反應30分鐘,室 溫反應1小時。反應後將反應液加於正己烷2 0 0毫升,析 出產物環戊二烯基鋰,以玻璃濾材濾出,加以乾燥。 〔具有二級碳原子直接鍵結於矽原子之結構的有機矽烷化 合物之製造〕 氮氣流下,一於·配備I拌-裝-置之200毫升施嫩克管反應 器饋入乾燥正戊烷5 0毫升,乾燥乙醚2 0毫升及四氯矽烷 8.09克(47.6毫莫耳),以正戊烷70毫升將上述製造之 環戊二烯基鋰7.2〇克(100毫莫耳)漿體化,以注射器於 室溫以1 0分鐘滴入。滴完後,於室溫攪拌24小時。反應 完後,以玻璃濾材去除反應液漿體中之氯化鋰,餾去正戊 烷,得二環戊二烯基二氯矽烷。 氮氣流下,於配備回流冷却器、攪拌裝置之200毫升 施嫩克管反應器饋入所得之二環戊二烯基二氯矽烷及正己 烷1 2 0毫升,加以溶解。加入乙醇鈉8 · 1 7克(1 2 0毫莫耳 ),於正已烷回流條件下反應4小時。反應後以玻璃濾材 濾除氯化鈉及未反應之乙醇鈉,蒸餾純化得產物二環戊二 烯基二乙氧基矽烷7.41克(29.9毫莫耳),收率爲62.8 %。 離析之二環戊二烯基二乙氧基矽烷以1Η - NMR、 G C — M S分析’結果如下。 ln NMR · 6.25 ppm ( m ^ 10H) ,1 2.8 p p m ( t,6 H ) -41 - (36) 1252232 ,3.9 1 ppm (q,4H) GC — MS: Mw 二 248’ Ci4H2〇〇2Si 又,所得二環戊二烯基二乙氧基矽烷1 〇〇克中之水分 及鈉、鋰含量以卡爾一費歇水分計及1CP—MS (高頻電漿 發光—質譜分析儀,橫河ANALYTICAL SYSTEMS公司製 ,商品名 “ Η P 4 5 0 0 ”)測定,結果 H 2 〇 = 1 7 p p m,L i < 1 〇 p p b,N a < 1 〇 p p b,適用作絕緣膜材料。 --.·-- .. .---_________— — .--- ......- -· · --. ......- * ^ " 比較例6 實施例1 〇之具有二級碳原子直接鍵結於矽原子之結 構的有機矽烷化合物之製造中,二環戊二烯基二氯矽烷與 乙醇鈉反應後,不濾除氯化鈉及未反應之乙醇鈉’加水萃 取去除可溶分以外,如同實施例1製造二環戊二烯二乙氧 基矽烷。 所得二環戊二烯基二乙氧基矽烷中之水分及鈉、鋰含 量,以卡爾一費歇水分計及ICP — MS測定,貝[J H20 = 130 ppm,Li< 10 ppb,Na< 10 ppb,不適用作絕緣膜材料。 發明效果 利用本發明,可達以下顯著效果。 本發明之第一效果在於,使用本發明之具有至少一個 二級烴基及/或三級烴基直接鍵結於矽原子之結構的有機 矽烷化合物,可提供用作半導體裝置層間絕緣膜中之低介 電材料的介電率低且機械強度高之材料。 -42- (37) 1252232 第二效果在於,採用本發明之具有至少一個二級烴基 及/或三級烴基直接鍵結於矽原子之結構的有機矽烷化合 物以PECVD形成層間絕緣膜,即可提供習知方法難以提 供之多孔性材料。 【圖式之簡單說明】 第1圖PECVD裝置之槪略結構圖。 弟—2 -圖I R--R A S--之-槪-略結構圖。----------- — t ΐ g元件對照表】 1 石 英 玻 璃 製 電 漿 源 2 成 膜 室 3 氣 化 器 4 真 空 排 氣 裝 置 5 矽 基 板 6 局 頻 電 源 7 匹 配 網 路 S 紅 外 線 9 偏 振 片 10 水 銀 • 鎘 警 碲 半 導體紅外線傳感器 -43-
Claims (1)
1252232 拾、申請專利範圍 ...........…’ 第92 1 020 1 2號專利申請案 中文申請專利範圍修正本 民國94年11月11日修正 1 · 一種絕緣膜用材料,其特徵爲:含具有至少一個 環狀二級脂肪烴基及/或非環狀三級脂肪烴基直接鍵結於 矽原子之構造的有機矽烷化合物所成,以化學氣相沈積法 形成者。 鲁 2 ·如申請專利範圍第1項之絕緣膜用材料,其中具有 非環狀三級脂肪烴基直接鍵結於矽原子之構造的有機矽烷 化合物,係如下述一般式(1 )
(式中R1、R2、R3表碳原子數1至20之烴基;R4表碳 原子數1至1〇之烴基或氫原子、a表1至3之整數)° 3. 如申請專利範圍第2項之絕緣膜用材料,其中一 般式(1 )之非環狀三級脂肪烴基係第三丁基或第三戊基 〇 4. 如申請專利範圍第1項之絕緣膜用材料’其中具 有非環狀三級脂肪烴基直接鍵結於矽原子之構造的有機砂 院化合物,係如下述一般式(2 ) 1252232 R5 (?)
R5 R5 R5 - C-Si—〇 R8 (式中R5、R6表碳原子數1至20之烴基,R7、R8表氫 原子或碳原子數1至20之烴基;b及c各表〇或1 ) 所示者。 5 .如申請專利範圍第4項之絕緣膜用材料,其中上 述一般式(2)之有機矽烷化合物,係第三丁基二烷基烷 氧基砂院。 6 ·如申請專利範圍第1項之絕緣膜用材料,其中具 有環狀二級脂肪烴基直接鍵結於矽原子之構造的有機矽烷 化合物,係如下述一般式(3 )
(式中r^rm'r11表碳原子數1至20之烴基;R9、 R10亦可互相結合形成環狀構造;R12表碳原子數1至 10之烴基或氫原子;d表1至3之整數,e表0至2之整 數,d+e表3以下之整數)。 7 ·如申請專利範圍第1項之絕緣膜用材料,其中一 般式(3 )之環狀二級脂肪烴基係環戊二烯基。 8 ·如申請專利範圍第1至7項中任一項之絕緣膜用 材料,其爲矽、碳、氧、氫以外之元素,來自製造原料之 雜質量不及10 ppb,且含水量不及50 ppm。 1252232 9.如申請專利範圍第1至7項中任一項之絕緣膜用 材料,其中化學氣相沈積法,係電漿激發化學氣相沈積法 (PECVD : Plasma Enhanced Chemical Vapor Deposition )° 1 0 .如申請專利範圍第8項之絕緣膜用材料,其中化 學氣相沈積法,係電漿激發化學氣相沈積法(PECVD : Plasma Enhanced Chemical Vapor Deposition) o 11· 一種一般式(1)
R2 -Si(OR4)4-a ,I R1—C- L (1 ) R3 (式中R1至R4、a同上述)所示之有機矽烷化合物之製 造方法,其特徵爲:使下述一般式(4) R2 R1-C—X R3 (4) (式中R1至R3同上述;X表氯原子、溴原子、_原子 ) 所示之有機鹵化物,與金屬鋰粒子反應所製造之,三,极碳 原子與鋰原子直接鍵結之有機鋰,與下述一般式(5) X,mSi ( OR4) 4- m ( 5 ) (式中R4同上述;X’表氟原子、氯原子、溴原子、換 原子,m表0至3之整數) 所示之鹵化烷氧基矽烷或四烷氧基矽烷反應者。 12. —種一般式(3) -3- 1252232
I SiR11e(〇R1V(d+e) (式中R9、R1G、R11、Ri2、d、e&d+e同上述)所示之有 機砂院化合物之製造方法’其特徵爲:使下述一般式(6 r HC—Y (式中R 、R1<3同上述;Y表氫原子、氯原子、溴原子或 碘原子) 所不之有機化合物,與使有機鋰或金屬鋰粒子反應製 造之二級碳原子與鋰原子直接鍵結之化合物,與下述一般 式(7 ) YfPSiRnq ( OR12) 4_ (p+ q) ( 7) (式中表氟*原子、氯原子、溴原子或碘原子,rii、Ri2 同上述;P表〇至4之整數,q表〇至2之整數,p+q表4以下 之整數) 所示之鹵化矽烷、鹵化烷氧基矽烷或四烷氧基矽烷反應, 進而殘留有直接鍵結於矽原子之鹵素原子時,使下述一般 式(8 ) R12OM ( 8 ) (式中Μ係鹼金屬,R12同上述) 所示鹼金屬烷氧化物反應後’藉過濾、蒸餾或管柱分離予 以精製。 -4- 1252232 1 3 . —種絕緣膜,其特徵爲··用如申請專利範圍第1 至8項中任一項之絕緣膜用材料中之有機矽院化合物,以 PECVD裝置成膜。 1 4 · 一種絕緣膜,其特徵爲:將如申請專利範圍第1 3 項之絕緣膜,以切斷三級碳原子與矽原子之鍵以上的溫度 作熱處理,而多孔化。 15·—種半導體裝置,其特徵爲:使用如申請專利範 圍第1 3或1 4項之絕緣膜。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002023988 | 2002-01-31 | ||
JP2002112130 | 2002-04-15 | ||
JP2002332100 | 2002-11-15 | ||
JP2002346225A JP4863182B2 (ja) | 2002-01-31 | 2002-11-28 | 有機シラン化合物を含んでなる絶縁膜用材料、その製造方法および半導体デバイス |
JP2002346226 | 2002-11-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW200303317A TW200303317A (en) | 2003-09-01 |
TWI252232B true TWI252232B (en) | 2006-04-01 |
Family
ID=27671168
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW92102012A TWI252232B (en) | 2002-01-31 | 2003-01-29 | Organosilane-containing material for insulation film, method for producing the same, and semiconductor device |
Country Status (4)
Country | Link |
---|---|
US (2) | US7160625B2 (zh) |
KR (1) | KR101227664B1 (zh) |
CN (1) | CN100367472C (zh) |
TW (1) | TWI252232B (zh) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI282124B (en) * | 2002-11-28 | 2007-06-01 | Tosoh Corp | Insulating film material containing an organic silane compound, its production method and semiconductor device |
DE10355038B4 (de) | 2003-04-02 | 2022-09-08 | Robert Bosch Gmbh | Verfahren zur Beschichtung einer Oberfläche |
JP4267994B2 (ja) * | 2003-09-17 | 2009-05-27 | 東京エレクトロン株式会社 | 半導体装置の低誘電率絶縁膜形成方法および低誘電率絶縁膜形成制御方法 |
JP4610379B2 (ja) * | 2004-05-31 | 2011-01-12 | 富士フイルム株式会社 | ケイ素含有化合物、該化合物を含有する組成物及び絶縁材料 |
JP4306607B2 (ja) * | 2004-12-24 | 2009-08-05 | 富士ゼロックス株式会社 | 電界効果トランジスタ |
KR101213035B1 (ko) * | 2005-01-12 | 2012-12-17 | 가부시키가이샤 트리케미컬 겐큐쇼 | 막 형성재료 및 막 형성방법 |
CN101611043B (zh) * | 2007-02-14 | 2013-03-13 | Jsr株式会社 | 含硅膜形成用材料、以及含硅绝缘膜及其形成方法 |
JP2008201982A (ja) * | 2007-02-22 | 2008-09-04 | Idemitsu Kosan Co Ltd | 多環脂環式化合物を前駆体物質とする薄膜、及びその製造方法 |
WO2009008424A1 (ja) * | 2007-07-10 | 2009-01-15 | Jsr Corporation | ケイ素化合物の製造方法 |
JP5015705B2 (ja) * | 2007-09-18 | 2012-08-29 | ルネサスエレクトロニクス株式会社 | 層間絶縁膜形成方法、層間絶縁膜、半導体デバイス、および半導体製造装置 |
JP4379637B1 (ja) | 2009-03-30 | 2009-12-09 | Jsr株式会社 | 有機ケイ素化合物の製造方法 |
JP5299260B2 (ja) * | 2009-12-24 | 2013-09-25 | 信越化学工業株式会社 | 固体材料の表面処理方法 |
JP6007662B2 (ja) | 2011-09-05 | 2016-10-12 | 東ソー株式会社 | 成膜材料、それを用いた封止膜、及びその用途 |
EP3190648B1 (en) * | 2014-09-05 | 2018-11-28 | LG Chem, Ltd. | Lithium electrode, lithium secondary battery comprising same, battery module comprising lithium secondary battery, and preparation method of lithium electrode |
KR101759891B1 (ko) * | 2015-06-23 | 2017-07-21 | (주)디엔에프 | 실리콘 전구체 및 이를 이용한 실리콘 함유 박막의 제조방법 |
US11679412B2 (en) | 2016-06-13 | 2023-06-20 | Gvd Corporation | Methods for plasma depositing polymers comprising cyclic siloxanes and related compositions and articles |
WO2017218561A1 (en) | 2016-06-13 | 2017-12-21 | Gvd Coproraton | Methods for plasma depositing polymers comprising cyclic siloxanes and related compositions and articles |
US11600486B2 (en) * | 2020-09-15 | 2023-03-07 | Applied Materials, Inc. | Systems and methods for depositing low-κdielectric films |
US11621162B2 (en) * | 2020-10-05 | 2023-04-04 | Applied Materials, Inc. | Systems and methods for forming UV-cured low-κ dielectric films |
EP4342918A1 (en) * | 2022-09-21 | 2024-03-27 | SABIC Global Technologies B.V. | Process for the synthesis of sterically crowded and synthetically challenging alkyl alkoxy silanes using organolithium reagents |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2974157A (en) * | 1954-08-04 | 1961-03-07 | Union Carbide Corp | Cyclopentadienyl vinyl silanes and process for making same |
US4711820A (en) * | 1986-06-17 | 1987-12-08 | Petrarch Systems Inc. | Method of siliconization of surfaces with lower alkyl silanes |
US4705725A (en) * | 1986-11-28 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Substrates with sterically-protected, stable, covalently-bonded organo-silane films |
JPH02192729A (ja) | 1989-01-20 | 1990-07-30 | Fujitsu Ltd | 絶縁層の製造方法 |
JPH0737467B2 (ja) * | 1989-05-26 | 1995-04-26 | 信越化学工業株式会社 | tert―ブチルトリアルコキシシランの製造方法 |
US5061514A (en) * | 1990-07-13 | 1991-10-29 | Olin Corporation | Chemical vapor deposition (CVD) process for plasma depositing silicon carbide films onto a substrate |
JP3115064B2 (ja) * | 1990-11-16 | 2000-12-04 | 東燃株式会社 | 新規シラン化合物の製造方法 |
JP2795135B2 (ja) * | 1993-06-07 | 1998-09-10 | 信越化学工業株式会社 | オルガノアルコキシシラン化合物の製造方法 |
JPH0748387A (ja) * | 1993-08-04 | 1995-02-21 | Shin Etsu Chem Co Ltd | tert−ブチルジアルコキシシラン及びその製造方法 |
CN1125481A (zh) * | 1994-03-11 | 1996-06-26 | 川崎制铁株式会社 | 评价用于形成绝缘膜的硅氧烷的方法、形成绝缘膜的涂布液及其制备方法、半导体器件用绝缘膜成型方法以及采用绝缘膜成膜法制备半导体器件的方法 |
JP2757767B2 (ja) * | 1994-03-30 | 1998-05-25 | 日本電気株式会社 | 半導体装置の製造方法 |
US5989998A (en) | 1996-08-29 | 1999-11-23 | Matsushita Electric Industrial Co., Ltd. | Method of forming interlayer insulating film |
KR100463858B1 (ko) * | 1996-08-29 | 2005-02-28 | 마츠시타 덴끼 산교 가부시키가이샤 | 층간절연막의형성방법 |
US6150549A (en) * | 1997-07-31 | 2000-11-21 | Nippon Mitsubishi Oil Corporation | Silane compound |
US6156471A (en) * | 1999-01-21 | 2000-12-05 | Canon Kabushiki Kaisha | Toner and image forming method |
US6303047B1 (en) * | 1999-03-22 | 2001-10-16 | Lsi Logic Corporation | Low dielectric constant multiple carbon-containing silicon oxide dielectric material for use in integrated circuit structures, and method of making same |
CN1297578A (zh) * | 1999-03-30 | 2001-05-30 | 捷时雅株式会社 | 硅氧化膜的形成方法 |
JP2000302791A (ja) * | 1999-04-20 | 2000-10-31 | Fujitsu Ltd | シリコン化合物、絶縁膜形成材料及び半導体装置 |
JP2000336312A (ja) * | 1999-05-28 | 2000-12-05 | Hitachi Chem Co Ltd | シリカ系被膜形成用塗布液、シリカ系被膜の製造法及び半導体装置 |
KR100677782B1 (ko) * | 2000-01-17 | 2007-02-05 | 제이에스알 가부시끼가이샤 | 절연막 형성용 재료의 제조 방법 |
KR100498834B1 (ko) * | 2000-04-04 | 2005-07-04 | 아사히 가세이 가부시키가이샤 | 절연 박막 제조용 코팅 조성물 |
JP2002201416A (ja) | 2000-12-28 | 2002-07-19 | Hitachi Chem Co Ltd | 半導体用シリカ系被膜形成用塗布液、半導体用シリカ系被膜及び半導体装置 |
US6583048B2 (en) * | 2001-01-17 | 2003-06-24 | Air Products And Chemicals, Inc. | Organosilicon precursors for interlayer dielectric films with low dielectric constants |
SG98468A1 (en) | 2001-01-17 | 2003-09-19 | Air Prod & Chem | Organosilicon precursors for interlayer dielectric films with low dielectric constants |
US6936537B2 (en) | 2001-06-19 | 2005-08-30 | The Boc Group, Inc. | Methods for forming low-k dielectric films |
-
2003
- 2003-01-23 KR KR1020030004560A patent/KR101227664B1/ko active IP Right Grant
- 2003-01-29 TW TW92102012A patent/TWI252232B/zh not_active IP Right Cessation
- 2003-01-30 US US10/354,052 patent/US7160625B2/en not_active Expired - Fee Related
- 2003-01-30 CN CNB031043100A patent/CN100367472C/zh not_active Expired - Lifetime
-
2006
- 2006-02-06 US US11/347,312 patent/US7413775B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
TW200303317A (en) | 2003-09-01 |
KR101227664B1 (ko) | 2013-01-29 |
US20060127683A1 (en) | 2006-06-15 |
KR20030065340A (ko) | 2003-08-06 |
US7160625B2 (en) | 2007-01-09 |
CN100367472C (zh) | 2008-02-06 |
CN1437228A (zh) | 2003-08-20 |
US20030180550A1 (en) | 2003-09-25 |
US7413775B2 (en) | 2008-08-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI252232B (en) | Organosilane-containing material for insulation film, method for producing the same, and semiconductor device | |
JP5003722B2 (ja) | 有機シロキサン化合物 | |
JP4438385B2 (ja) | 絶縁膜用材料、有機シラン化合物の製造方法、絶縁膜、及びそれを用いた半導体デバイス | |
US7816549B2 (en) | Metal-containing compound, its production method, metal-containing thin film, and its formation method | |
JP4591651B2 (ja) | 有機シラン化合物を含んでなる絶縁膜用材料、その製造方法および半導体デバイス | |
JP2008274365A (ja) | Si含有膜形成材料、Si含有膜及びその製造方法、並びに半導体デバイス | |
JP5353845B2 (ja) | 環状シロキサン化合物 | |
JP4863182B2 (ja) | 有機シラン化合物を含んでなる絶縁膜用材料、その製造方法および半導体デバイス | |
JP4333480B2 (ja) | Si含有膜形成材料、およびその用途 | |
JP4479190B2 (ja) | アルケニル基含有有機シラン化合物を含んでなる絶縁膜用材料、それを用いた絶縁膜および半導体デバイス | |
JP5019742B2 (ja) | 環状シロキサン化合物、Si含有膜形成材料、およびその用途 | |
TWI570130B (zh) | 成膜材料、使用該材料之封合膜以及其用途 | |
CN100444330C (zh) | 含有有机硅烷、有机硅氧烷化合物形成的绝缘膜用材料、其制造方法和半导体器件 | |
JP4341560B2 (ja) | Si含有膜形成材料、Si含有膜、Si含有膜の製法、及び、半導体デバイス | |
JP4385616B2 (ja) | 有機シラン化合物を含んでなる絶縁膜用材料、その製造方法および半導体デバイス | |
JP5040162B2 (ja) | アルケニル基含有有機シラン化合物から成るSi含有膜形成材料およびその用途 | |
JP4259217B2 (ja) | エステル基含有有機シラン化合物を含んでなる絶縁膜用材料およびそれを用いた絶縁膜 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Annulment or lapse of patent due to non-payment of fees |