WO2005068538A1 - ポリマーの製造方法、ポリマー、絶縁膜形成用組成物、絶縁膜の製造方法、および絶縁膜 - Google Patents
ポリマーの製造方法、ポリマー、絶縁膜形成用組成物、絶縁膜の製造方法、および絶縁膜 Download PDFInfo
- Publication number
- WO2005068538A1 WO2005068538A1 PCT/JP2005/000372 JP2005000372W WO2005068538A1 WO 2005068538 A1 WO2005068538 A1 WO 2005068538A1 JP 2005000372 W JP2005000372 W JP 2005000372W WO 2005068538 A1 WO2005068538 A1 WO 2005068538A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silane
- polymer
- group
- insulating film
- butyl
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 229910000077 silane Inorganic materials 0.000 claims abstract description 50
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 48
- 125000005843 halogen group Chemical group 0.000 claims abstract description 23
- 229920003257 polycarbosilane Polymers 0.000 claims abstract description 23
- 125000000962 organic group Chemical group 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 239000011229 interlayer Substances 0.000 abstract description 8
- 239000004065 semiconductor Substances 0.000 abstract description 8
- 238000009833 condensation Methods 0.000 abstract description 5
- -1 polysiloxane Polymers 0.000 description 158
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 50
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 45
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical compound CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 36
- 229910052719 titanium Inorganic materials 0.000 description 31
- 239000010936 titanium Substances 0.000 description 31
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 30
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 30
- 229910052726 zirconium Inorganic materials 0.000 description 30
- 239000007983 Tris buffer Substances 0.000 description 29
- 229910052799 carbon Inorganic materials 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000000576 coating method Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000011248 coating agent Substances 0.000 description 20
- HCOKJWUULRTBRS-UHFFFAOYSA-N propan-2-yloxysilane Chemical compound CC(C)O[SiH3] HCOKJWUULRTBRS-UHFFFAOYSA-N 0.000 description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 17
- 239000005977 Ethylene Substances 0.000 description 17
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 229930195729 fatty acid Natural products 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- BVNZLSHMOBSFKP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxysilane Chemical compound CC(C)(C)O[SiH3] BVNZLSHMOBSFKP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 125000005595 acetylacetonate group Chemical group 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 9
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- 241000233855 Orchidaceae Species 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 239000003738 black carbon Substances 0.000 description 8
- 229940126214 compound 3 Drugs 0.000 description 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
- XWQLYVIMMBLXPY-UHFFFAOYSA-N butan-2-yloxysilane Chemical compound CCC(C)O[SiH3] XWQLYVIMMBLXPY-UHFFFAOYSA-N 0.000 description 7
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- BJISXPRYXCKVSD-UHFFFAOYSA-J 3-oxobutanoate;titanium(4+) Chemical compound [Ti+4].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O.CC(=O)CC([O-])=O.CC(=O)CC([O-])=O BJISXPRYXCKVSD-UHFFFAOYSA-J 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229940022663 acetate Drugs 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- 125000005997 bromomethyl group Chemical group 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 6
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 5
- 239000005052 trichlorosilane Substances 0.000 description 5
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 5
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- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000005456 alcohol based solvent Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
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- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000005055 methyl trichlorosilane Substances 0.000 description 4
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 4
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
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- 239000007787 solid Substances 0.000 description 4
- ASEHKQZNVUOPRW-UHFFFAOYSA-N tert-butyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C(C)(C)C ASEHKQZNVUOPRW-UHFFFAOYSA-N 0.000 description 4
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
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- KBFAHPBJNNSTGX-UHFFFAOYSA-N trimethoxy-(3-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC([Si](OC)(OC)OC)=C1 KBFAHPBJNNSTGX-UHFFFAOYSA-N 0.000 description 1
- XOAJIYVOSJHEQB-UHFFFAOYSA-N trimethyl trimethoxysilyl silicate Chemical compound CO[Si](OC)(OC)O[Si](OC)(OC)OC XOAJIYVOSJHEQB-UHFFFAOYSA-N 0.000 description 1
- RDDMOMIMRPHKSZ-UHFFFAOYSA-N trimethyl-(3-trimethylsilylphenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC([Si](C)(C)C)=C1 RDDMOMIMRPHKSZ-UHFFFAOYSA-N 0.000 description 1
- IXJNGXCZSCHDFE-UHFFFAOYSA-N triphenoxy(phenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 IXJNGXCZSCHDFE-UHFFFAOYSA-N 0.000 description 1
- MUCRQDBOUNQJFE-UHFFFAOYSA-N triphenoxy(triphenoxysilyl)silane Chemical compound C=1C=CC=CC=1O[Si]([Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 MUCRQDBOUNQJFE-UHFFFAOYSA-N 0.000 description 1
- YRUALOZSEADDBR-UHFFFAOYSA-N triphenyl triphenoxysilyl silicate Chemical compound C=1C=CC=CC=1O[Si](O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 YRUALOZSEADDBR-UHFFFAOYSA-N 0.000 description 1
- IVZTVZJLMIHPEY-UHFFFAOYSA-N triphenyl(triphenylsilyloxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IVZTVZJLMIHPEY-UHFFFAOYSA-N 0.000 description 1
- QCKKBOHAYRLMQP-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[SiH](OC(C)(C)C)OC(C)(C)C QCKKBOHAYRLMQP-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
- H01L21/3121—Layers comprising organo-silicon compounds
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System 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
Definitions
- the present invention relates to a method for producing a polymer, a polymer, a composition for forming an insulating film, a method for producing an insulating film, and an insulating film.
- CVD Chemical Vapor
- a silica (SiO 2) film formed by a vacuum process such as a deposition method is often used.
- a coating-type insulating film called a SOG (Spin on Glass) film which is mainly composed of a hydrolysis product of tetraalkoxylan. It has become.
- an interlayer insulating film having a low relative dielectric constant which is mainly composed of polyorganosiloxane and is called organic SOG, has been developed.
- a composition comprising a mixture of fine particles obtained by condensing alkoxysilane in the presence of ammonia and a basic partial hydrolyzate of alkoxysilane (Japanese Unexamined Patent Application Publication No. No. 263045, JP-A-5-315319), and a coating solution obtained by condensing a basic hydrolyzate of a polyalkoxysilane in the presence of ammonia (JP-A-11-340219, JP-A-11-340219). — No. 340220) has been proposed.
- the materials obtained by these methods are not suitable for industrial use because the properties of the reaction products are not stable and the coatings have large variations in relative dielectric constant, crack resistance, mechanical strength, adhesion, etc. It was not suitable for production.
- a method has been proposed in which a coating solution is prepared by mixing a polycarbosilane solution and a polysiloxane solution to form a low dielectric constant insulating film (Japanese Patent Application Laid-Open No. 2001-127152). And siloxane domain There has been a problem that they are dispersed in the coating film in a uniform state.
- the organometallic silane bonding property is determined by a method using an organic silicate polymer obtained by producing a silane oligomer containing a carbon bridge and then subjecting the silane oligomer to hydrolysis and condensation.
- the present invention is to form a film which can be suitably used as, for example, an interlayer insulating film in a semiconductor device or the like, has a small relative dielectric constant, has excellent mechanical strength and adhesion, and has uniform film quality. It is an object of the present invention to provide a method for producing a polymer and a polymer.
- Another object of the present invention is to provide a composition for forming an insulating film, a method for producing an insulating film, and an insulating film using the polymer of the present invention.
- the method for producing a polymer according to the present invention comprises:
- R 1 —R 4 are the same or different and each represents a monovalent organic group or a hydrogen atom
- X represents a halogen atom
- Y represents a halogen atom or an alkoxy group
- k is an integer of 0-3.
- m and n are the same or different and represent an integer of 0 to 2.
- the (B) hydrolyzable group-containing silane monomer is a compound represented by the following general formula (4) and the following general formula (5)
- the group strength of the compound represented by the formula can be at least one selected silani conjugate.
- R 5 represents a hydrogen atom, a fluorine atom or a monovalent organic group
- X represents a halogen atom or an alkoxy group
- a represents an integer of 0-3.
- R 6 and R 7 are the same or different, each represents a monovalent organic group, b and c are the same or different, and represent an integer of 0-2, and R 8 is an oxygen atom, a phenylene group. Or — (CH)-
- e represents an integer of 16
- Y and Z are the same or different and represent a halogen atom or an alkoxy group
- d represents 0 or 1.
- the polymer according to the present invention is obtained by the above-described method for producing a polymer according to the present invention.
- composition for forming an insulating film according to the present invention contains the above-described polymer according to the present invention and an organic solvent.
- the method for producing an insulating film according to the present invention can include applying the above-described composition for forming an insulating film according to the present invention to a substrate and heating the composition to 30 to 450 ° C.
- the silica-based insulating film according to the present invention is obtained by the above-described method for manufacturing an insulating film according to the present invention.
- a hydrolyzable group-containing silane monomer is reacted with (B) a hydrolyzable group-containing silane monomer in the presence of polycarbosilane.
- a polymer obtained by reacting a polysiloxane derived from the above with (A) polycarbosilane can be obtained.
- a partially co-condensed polymer can be obtained by hydrolyzing and condensing (B) a hydrolyzable group-containing silane monomer in the presence of (A) polycarbosilane having a hydrolyzable group. .
- a film-forming composition containing such a specific polymer an insulating film having a small relative dielectric constant, excellent mechanical strength and excellent adhesion, and no phase separation in the film can be obtained.
- the polymer of the present invention is obtained by hydrolyzing and condensing (B) a hydrolyzable group-containing silane monomer in the presence of (A) polycarbosilane. is there.
- R 1 —R 4 are the same or different and each represents a monovalent organic group or a hydrogen atom
- X represents a halogen atom
- Y represents a halogen atom or an alkoxy group
- k is an integer of 0-3.
- m and n are the same or different and represent an integer of 0 to 2.
- Polycarbosilane can be polymer (I).
- the polymer (I) comprises (a) a compound represented by the following general formula (1), (b) a compound represented by the following general formula (2), and a compound represented by the following general formula (3). It is obtained by reacting at least one selected from group powers in an organic solvent in the presence of at least one of an alkali metal and an alkaline earth metal.
- R 1 to R 4 are the same or different and are a hydrogen atom or a monovalent organic group.
- the monovalent organic group include linear or branched aliphatic groups having 11 to 10 carbon atoms such as an alkyl group, an alkenyl group, and an alkynyl group; a cycloalkyl group, a cycloalkyl group, and a bicycloalkyl group.
- Alicyclic groups having 3 to 20 carbon atoms such as groups; aryl groups having 6 to 20 carbon atoms; and aralkyl groups having 6 to 20 carbon atoms.
- alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an isopentyl group, and a neopentyl group.
- alkyl group examples include a butyl group, a probel group, a 3-butyr group, and a 3-pentyl group.
- alkyl group examples include a propargyl group, a 3-methylpropagyl group, and a 3-ethylpropagyl group.
- Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a norvol group.
- aryl group examples include a phenyl group, a tolyl group, a xylyl group, an ⁇ -naphthyl group, a 13-naphthyl group, an ⁇ -thiophene group, and an
- Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, and a phenylbutyl group.
- Examples of the halogen atom represented by X and ⁇ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- Examples of R in the alkoxy group (1-OR) represented by ⁇ include the same groups as those described above for the alkyl group and aryl group in R 1 to R 4 .
- the weight average molecular weight in terms of polystyrene of the polycarbosilane of the component (A) is preferably 400 to 50,000, more preferably 500 to 10,000, more preferably 500 to 3,000. It is even more preferred. If the weight average molecular weight in terms of polystyrene of the component (B) exceeds 50,000, layer separation may occur with the component (A) and a uniform film may not be formed.
- I-Danied Compound 1 examples include tetrachlorocarbon, tetrabromocarbon, tetrachodcarbon, chlorohonolem, bromohonolem, rhodoform, and methyltrichloride.
- One of these compounds 1 can be used alone, or two or more can be used as a mixture.
- Examples of the compound represented by the general formula (2) include tetrachlorosilane, tetrabromosilane, tetraodosilane, trichlorosilane, tribromosilane, triiodosilane, Methyltrichlorosilane, ethyltrichlorosilane, n -propyltrichlorosilane, isopropyltrichlorosilane, n -butyltrichlorosilane, t-butyltrichlorosilane, cyclohexyltrichlorosilane, phenethyltrichlorosilane, 2-norbornyltrichlorosilane orchids, vinyl trichlorosilane, phenylalanine trichlorosilane, Mechirutoribu port Moshiran, Echiru tribromo silane, n
- Dimethyldichlorosilane getyldichlorosilane, di-n-propyldichlorosilane, diisopropyldichlorosilane, di-n-butyldichlorosilane, di-t-butyldichlorosilane, dicyclohexyldichlorosilane, diphenethyldichlorosilane, di-2-norvol -Dichlorosilane, dibutyldichlorosilane, diphenyldichlorosilane, dimethyldibromo Silane, getyl dibute mosilane, di-n-propyl dibute mosilane, di-isopropyl dibute mosilane, di-n-butyl dibute mosilane, di-t-butyl dibute mosilane, dicyclohexyl dibute mosilane, diphenethyl dibute
- Dipheninolase n -propoxysilane Dipheninolase iso-propoxysilane, dipheninolene n -butoxysilane, diphenylene sec-butoxysilane, diphenylene tert-butoxysilane, diphenyldiphenoxysilane, Silicon compounds such as divinyltrimethoxysilane can be exemplified.
- i-conjugated compound 3 examples include chloromethyltrichlorosilane, bromomethyltrichlorosilane, odomethyltrichlorosilane, chloromethylmethyldichlorosilane, and chloromethyldichlorosilane.
- Tyldichlorosilane chloromethyl- n -propyldichlorosilane, chloromethinoleisopropinoresichlorosilane, chloromethinole n -butinoresiclo silane silane, chloromethinole t-butinoresichlorosilane, chloromethinolecyclohexinoresichlorosilane, chloromethinolephneetino Resichlorosilane, chloromethinolebininoresichlorosilane, methyl phenyldichlorosilane, bromomethylmethyldichlorosilane, bromomethylethyldichlorosilane, bromomethyl- n- propyldichlorosila Bromomethylisopropyldichlorosilane, bromomethyl- n -butyldichlorosilane, bromomethyl-t-butyldichlorosi
- the polycarbosilane (A) is the following polymer (I).
- the usage ratio of the compound 1 to the compound 2 and the Z or the compound 3 is preferably 0.01 to 100, more preferably 0.1 to 10, and particularly preferably 0.5 to 5 in a molar ratio.
- the degree of polymerization of the produced polymer can be improved.
- Lithium, potassium, and sodium are used as alkali metals that can be used in the present invention, and magnesium is used as an alkaline earth metal. Magnesium is most preferably used in the present invention.
- the alkali metal and the alkaline earth metal are used to form a carbon-silicon bond by reductively removing a halogen atom or an alkoxy group from compound 1, compound 2 and Z or compound 3.
- the use amount thereof is preferably 1.0 to 1.5 molar equivalents relative to the total amount of the carbon halogen bond and the carbon alkoxy group bond of compound 1, compound 2 and Z or compound 3.
- the reaction can be promoted by irradiating the reaction solution with ultrasonic waves as necessary.
- the ultrasonic frequency used here is desirably about 10-70KHz!
- an ether-based solvent is preferred, and an organic solvent can be used.
- the yield of the desired soluble silicon oligomer tends to be low with the hydrocarbon solvent used in the ordinary Kipping reaction.
- ether solvent examples include getyl ether, di-n-propyl ether, diisopropinoleatenole, dibutynoleatenole, etinolepropinoleatenole, aniso monole, pheneto monole, dipheninoleate.
- diethylene glycolone resin methylene ether, diethylene glycol diethylene glycol, diethylene glycol dibutylinyl ether, dimethylene glycol methyl ether ether, dipropylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene Glycol dibutinolate ether, dipropylene glycolone methylenetoleatene, ethylene glycolone resin methineoleatene, ethylene glycoloneregetineoleatene, ethylene glycoloneleatene Noreethenole, ethylenglycorone methinoleetenole, propylene glycolone resin methinoleatenole, propylene glycol diethylene terephthalate, propylene glycol dibutynolete tere, propylene glycol methylethyl ether, tetrahydrofuran, dioxane To name Can do. Of these, getyl ether,
- water is removed from these ether solvents in advance.
- a degassing distillation method in the presence of sodium-benzophenone ketyl and the like are preferred.
- the amount of these solvents to be used is not particularly limited, but is preferably 1 to 30 parts by weight, more preferably 2 to 20 parts by weight, based on the total amount of compound 1, compound 2 and Z or compound 3. is there.
- the reaction temperature of the polymer (I) is preferably 0 to 150 ° C, more preferably 30 to 100 ° C.
- the reaction temperature is lower than 0 ° C, the reaction rate is low and the productivity does not increase.
- the reaction temperature is higher than 150 ° C, the reaction becomes complicated and the solubility of the obtained polymer tends to decrease.
- the reaction is usually preferably performed in an inert gas such as argon or nitrogen.
- the polymer (I) obtained by the above method is further reacted with an alcohol or an organic acid in an organic solvent when (i) ⁇ in the polymer (I) has a halogen atom. Or (ii) reacting the reducing agent in an organic solvent.
- the polymer (I) having an unreacted hydrolyzable halogen atom at the molecular terminal or side chain is reacted with an alcohol or an organic acid to make the halogen atom more stable in an alkoxy group or ester.
- the group can be substituted.
- Examples of the alcohol include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-pentanol, i-pentanol, 2-methylbutanol, sec-pentanol, and t-pen Tanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethynolbutanol, sec-heptanol, 3-heptanol, n-octanol, 2-ethylhexanol, sec— Tertanol, n-nor alcohol, 2,6-dimethyl-4-heptanol, n-decanol, sec- decyl alcohol, trimethyl alcohol, sec-tetradecyl alcohol, sec-heptadecyl
- Ethylene glycolone 1,2-propylene glycol, 1,3-butylene glycol, 2,4-pentanediol, 2-methyl-2,4 pentanediol, 2,5 xanediol, 2,4 heptanediol, 2-ethyl-1, 3
- Polyvalent phenols such as xanediol, diethylene glycol, dipropylene glycol, triethylene glycol, and tripropylene glycol;
- Examples of the organic acid include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, and sebacic acid.
- the alcohol or acid can be used alone or in combination of two or more.
- the amount of the alcohol or acid used depends on the halo of the polymer in which each hydroxyl group remains. It is at least equivalent, more preferably 1.0-4.0 times equivalent to the gen atom.
- the solvent used at this time is not particularly limited as long as it does not react with the alcohol or acid to be used, but benzene, toluene, xylene, mesitylene and the like, which are usually preferable for aromatic solvents, are used. Can be mentioned. These can be used alone or in combination of two or more.
- an organic amine which forms a salt in combination with halogenated hydrogen and has no active hydrogen.
- Typical organic amines include pyridine, pyrrole, picoline, diazabicyclooctane, diazabicyclononane, diazabicycloundecene, trimethylamine, triethylamine, tripropylamine, tributylamine and the like. be able to. One or more of these alkali catalysts may be used simultaneously.
- the polymer (I) having an unreacted hydrolyzable halogen atom at the molecular terminal or the polymer obtained by the method (i) is reduced to a reducing agent.
- the substituent on the silicon atom can be replaced with a stable hydrogen atom.
- Such reducing agents include, for example, LiAlH, NaH, LiBu BH, (CH) BH, BH,
- LiAlH, NaH, BH and NaBH can be mentioned as more preferable examples.
- the amount of the reducing agent to be used is at least equivalent to the halogen atom of the polymer in which the hydrogen atoms in the reducing agent remain, preferably 1.0 to 4.0 times equivalent.
- the solvent to be used at this time is not particularly limited as long as it does not react with the reducing agent, and the same solvent as the ether solvent exemplified above, which is usually preferable for the ether solvent, can be used. . These can be used alone or in combination of two or more.
- the reaction temperature at this time is preferably -78 ° C-+ 60 ° C. If the reaction temperature is lower than 78 ° C, the reaction will be slow and productivity will not increase. If the reaction temperature is higher than + 60 ° C, the solubility of the reaction product will decrease and the production yield of the polymer will tend to decrease. Further, the reaction is usually preferably carried out in an inert gas such as argon or nitrogen.
- the polymer of the present invention can be used in the presence of the above (A) polycarbosilane, It is obtained by hydrolytic condensation of a water-decomposable group-containing polymer.
- the term "hydrolysable group” refers to a group that can be hydrolyzed during production of the polymer of the present invention.
- Specific examples of the hydrolyzable group include, but are not particularly limited to, for example, a hydrogen atom bonded to a silicon atom, a halogen atom, a hydroxy group, an alkoxy group, an acyloxy group, a sulfone group, a methane sulfone group, and a trifluoromethane sulfone group. Groups.
- the hydrolyzable group-containing polymer is a compound represented by the following general formula (4) and at least one silane conjugate selected from the group power of the compound represented by the following general formula (5). There can be.
- R 5 represents a hydrogen atom, a fluorine atom or a monovalent organic group
- X represents a halogen atom or an alkoxy group
- a represents an integer of 0-3.
- R 6 and R 7 are the same or different, each represents a monovalent organic group, b and c are the same or different, and represent an integer of 0-2, and R 8 is an oxygen atom, a phenylene group. Or — (CH)-
- e represents an integer of 16
- Y and Z are the same or different and represent a halogen atom or an alkoxy group
- d represents 0 or 1.
- R 5 is a hydrogen atom, a fluorine atom or a monovalent organic group.
- the monovalent organic group include an alkyl group, an aryl group, an aryl group, a glycidyl group, and a vinyl group.
- R 5 is preferably a monovalent organic group, particularly an alkyl group or a phenyl group.
- examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and the like, and preferably have 115 carbon atoms.
- These alkyl groups may be linear or branched, and may be further substituted with a hydrogen atom, a fluorine atom, an amino group, or the like.
- Examples of the aryl group include a phenyl group, a naphthyl group, a methylphenyl group, an ethylphenyl group, a chlorophenyl group, a bromophenyl group, and a fluorophenyl group.
- hydrocarbon moiety of the alkoxy group of X is exemplified as a monovalent organic group of What was given can be applied as it is.
- compound 4 Specific examples of the compound represented by the general formula (4) (hereinafter also referred to as “compound 4”) include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-iso-propoxysilane, tetra-n-butoxysilane, tetra- sec butoxysilane, tetra-tert-butoxysilane, tetraphenoxysilane, trimethoxysilane, triethoxysilane, tri-n-propoxysilane, tri-isopropoxysilane, tri-n-butoxysilane, tri-sec-butoxysilane, tri-tert-butoxysilane, trif Enoxysilane, fluorotrimethoxysilane, fluorotriethoxysilane, fluorotory n-propoxysilane, fluorotory iso-propoxysilane, fluorotory
- Compound 4 is preferably methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltriisopropoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, vinyltrimethoxysilane, vinyltrimethoxysilane.
- examples of the monovalent organic group represented by R6 and R7 include the same organic groups as those in the general formula (4).
- the compounds of the general formula (5) where d is 0 include hexaclo disilane, hex submodi silane, hexiodosidisilane, hexamethoxydisilane , Hexethoxydisilane, hexaphenoxydisilane, 1,1,1,2,2-pentamethoxy-2-methyldisilane, 1,1,1,2,2-pentaethoxy-2-methyldisilane, 1,1,1,2,2-pentaphenoxy 2-methyldisilane, 1,1,1,2,2-pentamethoxy-2-ethylethylsilane, 1,1,1,2,2-pentaethoxy 2-ethyldisilane, 1,1,1,2,2-pentaphenoxy 2-ethyldisilane, 1,1,1,2,2-pentaphenoxy 2-ethyldisilane, 1,1,1,2,2-pentamethoxy-2-phenyldisilane, 1,1,1,2,2-penta Ethoxy 2-phen
- At least one silani conjugate having the group power of the compounds 4 and 5 selected in the presence of (A) polycarbosilane (polymer (1)) is hydrolyzed.
- a specific catalyst can be used.
- the catalyst at least one selected from the group consisting of an alkali catalyst, a metal chelate catalyst, and an acid catalyst can be used.
- alkali catalyst examples include sodium hydroxide, potassium hydroxide, lithium hydroxide, pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, monoethanolamine, diethanolamine, dimethyl Monoethanolamine, monomethyljetanolamine, triethanolamine, diazabicyclooctane, diazabicyclononane, diazabicycloundecene, tetramethylammonium-dimethylhydroxide, tetraethylammonium-dimethylhydroxide, tetrapropylammonium Demoxide mouth oxide, tetrabutylammonium-Demoxide mouth oxide, ammonia, methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, pentylamine, octylamine, noni Amin, Deshiruamin, N, N-Jimechiruamin, N, N-Je
- organic amines preferably amines, or alkylamines
- organic amine salts particularly preferred are organic amine salts, and oxides at the tetraalkyl ammonium hydroxide.
- organic amine salts particularly preferred are organic amine salts, and oxides at the tetraalkyl ammonium hydroxide.
- organic amine salts particularly preferred are organic amine salts, and oxides at the tetraalkyl ammonium hydroxide.
- oxides at the tetraalkyl ammonium hydroxide may be used simultaneously.
- the metal chelate catalyst examples include triethoxy mono (acetyl acetate) titanium, tree n propoxy 'mono (acetyl acetate) titanium, tree i propoxy' mono (acetyl acetate) titanium, tri- n-butoxy mono (acetyl acetate) titanium, tri-sec butoxy mono (acetyl acetate) titanium, tree t butoxy mono (acetyl acetate) titanium, diethoxy'bis (acetyl acetate) Titanium, G-propoxy 'bis (acetyl acetate) Titanium, G i-propoxy'bis (acetyl acetate) Titanium, G-butoxy bis (acetyl acetate) titanium, di-sec butoxy bis (Acetyl acetate toner) titanium, G-butoxy bis (acetyl acetate toner) titanium, Monoethoxy.tris (acetylacetonato) titanium, mono-n-propoxy 'tris (
- Aluminum chelates such as tris (acetylacetonato) anoremium and tris (ethylinoacetoacetate) anoremini;
- a chelate conjugate of titanium or aluminum particularly preferably a chelate of titanium.
- metal chelate catalysts may be used simultaneously.
- Examples of the acid catalyst include inorganic acids such as hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, and boric acid; acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, and the like.
- inorganic acids such as hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, and boric acid
- the amount of the catalyst to be used is generally 0.0001-10 mol, preferably ⁇ 0.00005, per 1 mol of the total amount of the groups represented by X, ⁇ and Z in compounds 4 and 5. — 5 moles. Catalyst usage Is within the above range, there is little danger of polymer precipitation during the reaction.
- the temperature at which the compounds 4 and 5 are hydrolyzed is usually 0 to 100 ° C, preferably 15 to 80 ° C.
- complete 311 hydrolyzed condensate refers to (A) polycarbosilane and the hydrolyzable groups in compounds 4 and 5 are hydrolyzed 100% to form SiOH groups, and To form a siloxane structure by condensation.
- the condensate is preferably a hydrolyzed condensate of (A) polycarboxylic acid and compound 4 because the resulting composition has better storage stability.
- the amount of the compound 4 or 5 to be used with respect to (A) polycarbosilane is determined based on (A) 100 parts by weight of polycarbosilane and 500 to 4000 parts by weight of the total component power of the conjugates 4 and 5. Preferably it is 1000-30000 parts by weight.
- the weight average molecular weight of the polymer in terms of polystyrene is usually 1,500 to 500,000, preferably a force S ⁇ , and 2,000 to 200,000, more preferable than a force S ⁇ 2,000-100,000. If the polymer has a polystyrene-equivalent weight average molecular weight of less than 1,500, the desired relative dielectric constant may not be obtained.On the other hand, if it exceeds 500,000, the in-plane uniformity of the coating film may be poor. There is.
- composition for forming a film Components such as an organic polymer and a surfactant may be added to the composition for forming an insulating film of the present invention (hereinafter, referred to as “composition for forming a film”) in addition to the polymer of the present invention.
- Examples of the organic polymer include a (meth) acrylic polymer and a compound having a polyalkylene oxide structure.
- Examples of the compound having a polyalkylene oxide structure include a polymethylene oxide structure, a polyethylene oxide structure, a polypropylene oxide structure, a polytetramethylene oxide structure, and a polybutylene oxide structure.
- polyoxymethylene alkyl ethers polyoxyethylene alkyl ethers, polyoxyethylene ethylene phenyl ethers, polyoxyethylene ester ethers, polyoxyethylene lanolin derivatives, and alkylphenol formalin condensates Ethylene oxide derivative, polyoxyethylene polyoxypropylene block copoly Ether-type compounds such as polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene glycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene fatty acid alkanolamide sulfate, etc.
- Examples thereof include compounds, ether compounds such as polyethylene glycol fatty acid ester, ethylene glycol fatty acid ester, fatty acid monoglyceride, polyglycerin fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, and sucrose fatty acid ester.
- ether compounds such as polyethylene glycol fatty acid ester, ethylene glycol fatty acid ester, fatty acid monoglyceride, polyglycerin fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, and sucrose fatty acid ester.
- Examples of the polyoxyethylene polyoxypropylene block copolymer include compounds having the following block structures.
- J represents 1-90
- k represents 10-99
- 1 represents 0-90.
- polyoxyethylene alkyl ether polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene polyoxypropylene anolequinolate ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene sorbitan fatty acid Ether-type compounds such as esters and polyoxyethylene sorbitol fatty acid esters can be mentioned as more preferred examples. These may be used alone or in combination of two or more.
- the surfactant examples include a nonionic surfactant, an anionic surfactant, a thione surfactant, an amphoteric surfactant, and the like. Further, a fluorine surfactant, silicone Surfactants, polyalkylene oxide-based surfactants, poly (meth) phthalate-based surfactants, and the like, and preferably fluorine-based surfactants and silicone-based surfactants. .
- fluorinated surfactant examples include 1,1,2,2-tetrafluorooctyl (1,1,2,2-tetrafluoropropyl) ether and 1,1,2,2-tetrafluoropropyl Octyl hexyl ether, octaethylene glycol di (1,1,2,2-tetrafluorobutyl) ether, hexethyl Lenglycol (1,1,2,2,3,3-hexafluoropentyl) ether, octapropylene glycol di (1,1,2,2-tetrafluorobutyl) ether, hexapropylene glycol di (1, 1,2,2,3,3-hexafluoropentyl) ether, sodium perfluorododecylsulfonate, 1,1,2,2,8,8,9,9,10,10-decofodododecane, 1, 1,2,2,3,3-hexafluorodecane, N- [3- (
- silicone surfactant examples include SH7PA, SH21PA, SH30PA, and ST94.
- PA available from Toray “Dowko Jung” Silicone Co., Ltd.
- SH28PA and SH30PA are particularly preferable.
- the amount of the surfactant to be used is generally 0.0001 to 10 parts by weight based on the polymer (completely hydrolyzed condensate). These may be used alone or in combination of two or more.
- the polymer of the present invention (hydrolyzed condensate) and, if necessary, further additives can be dissolved or dispersed in an organic solvent.
- Examples of the organic solvent that can be used at this time include at least one selected from the group consisting of alcohol solvents, ketone solvents, amide solvents, ester solvents, and aprotic solvents.
- alcoholic solvents include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-pentanol, i-pentanol, 2-methylbutanol, and sec-pentanol pentanol, t-pentanol, 3-methoxybutanol, n hexanol, 2-methyl pentanol, sec hexanol 2-E chill-butanol, sec Putanoru, 3 Putanoru, n- Okutanoru, hexanol 2 chill, s ec - Okutanoru, n - Nol alcohol, 2,6 dimethyl 4-butanol, n-decanol, sec- decyl alcohol, trimethyl nol alcohol sec-tetratesinoleanol reconole, sec p
- Ethylene glycolone 1,2-propylene glycol, 1,3-butylene glycol, 2,4-pentanediol, 2-methyl-2,4 pentanediol, 2,5 xanediol, 2,4 heptanediol, 2-ethyl-1, 3
- Polyhydric alcohol solvents such as xanediol, diethylene glycol, dipropylene glycol, triethylene glycol, and tripropylene glycol;
- One or more of these alcohol solvents may be used in combination. May be used at times.
- Ketone solvents include acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, getyl ketone, methyl i-butyl ketone, methyl n-pentyl ketone, ethyl n-butyl ketone, methyl n-hexyl ketone, and di-ketone.
- i-Butyl ketone trimethylnonanone, cyclohexanone, 2-hexanone, methylcyclohexanone, 2,4-pentanedione, acetoninoleacetone, acetophenone, fencheon, and other acetylene acetone, 2,4-hexandione, 2,4 heptanedione, 3,5 heptanedione, 2,4 octanedione, 3,5 octanedione, 2,4-nonanedione, 3,5-nonanedione, 5-methinolay 2,4-hexanedione, 2,2,6 , 6—tetramethinole 3,5 heptanedione, to 1, 1, 1, 5, 5, 5— Examples include j8-diketones such as xafluoro-2,4-heptanedione. One or more of these ketone solvents may be used simultaneously.
- amide solvents examples include formamide, N-methylformamide, N, N-dimethylformamide, N-ethylformamide, N, N-getylformamide, acetoamide, N-methylacetamide, and N, N-dimethylacetamide.
- These amide solvents may be used alone or in combination of two or more.
- ester solvents examples include getyl carbonate, ethylene carbonate, propylene carbonate, getyl carbonate, methyl acetate, ethyl acetate, ⁇ -butyrolataton, ⁇ -valerolatane, ⁇ -propyl acetate, i-propyl acetate, n-butyl acetate, and acetic acid.
- aprotic solvents include acetonitrile, dimethyl sulfoxide, N, N, ⁇ ', ⁇ '-tetraethylsulfamide, hexamethylphosphoric triamide, ⁇ methylmorpholone, ⁇ -methylphenolylamine, ⁇ -ethylpyrrole , ⁇ -methyl- ⁇ -pyrroline, ⁇ -methylpiperidine, ⁇
- the total solid concentration of the film-forming composition of the present invention thus obtained is preferably 2 to 30% by weight, and is appropriately adjusted depending on the purpose of use.
- the total solid content of the film-forming composition is 2 to 30% by weight, the thickness of the coating film is in an appropriate range, and the storage stability is more excellent.
- the adjustment of the total solid content concentration is performed, if necessary, by concentration and dilution with the above organic solvent.
- the insulating film of the present invention can be obtained by applying the composition for film formation to form a coating film, and then heating the coating film.
- the film-forming composition of the present invention is applied to a substrate such as silicon wafer, SiO wafer, or SiN wafer.
- coating methods such as spin coating, dipping, roll coating, and spraying are used.
- the film thickness is about 0.05 to 2.5 m in a single coating, and about 0.1 to 5.0 m in a double coating. Can be formed. Then dry at room temperature Alternatively, by heating and drying at a temperature of about 80 to 600 ° C, usually for about 5 to 240 minutes, a vitreous or macromolecular coating film can be formed.
- a hot plate, an oven, a furnace, or the like can be used, and the heating atmosphere may be air, a nitrogen atmosphere, an argon atmosphere, a vacuum, or a decompression controlled oxygen concentration. It can be performed below.
- heating can be performed stepwise, or an atmosphere such as nitrogen, air, oxygen, or reduced pressure can be selected.
- the composition for film formation can be applied to a substrate and heated to 30 to 450 ° C. under irradiation with high energy rays.
- the silica-based insulating film of the present invention thus obtained has a film density of usually 0.35-1.
- the film density is less than 0.35 gZcm 3 , the mechanical strength of the coating film will decrease, while if it exceeds 1.2 g / cm 3 , a low dielectric constant cannot be obtained.
- the relative dielectric constant of the insulating film of the present invention is usually 3.2-1.2, preferably 3.0-1.5, and more preferably 2.7-1.8.
- the insulating film of the present invention is characterized by having a large number of silicon carbon bonds in the film structure. Due to this feature, it is excellent in insulation, uniformity of coating film, dielectric constant, elasticity of coating film, and adhesion of coating film.
- the insulating film of the present invention has a low relative dielectric constant and is excellent in crack resistance, mechanical strength, and adhesion, so that it is suitable for use in semiconductor devices such as LSI, system LSI, DRAM, SDRAM, RDRAM, and D-RDRAM.
- Protective films such as interlayer insulating films and etching stopper films, surface coat films for semiconductor devices, intermediate layers in semiconductor manufacturing processes using multilayer resists, interlayer insulating films for multilayer wiring boards, protective films and insulating films for liquid crystal display devices It is useful for such applications.
- Sample A polymer (hydrolysis condensate) lg was prepared by dissolving in 100 cc of tetrahydrofuran using tetrahydrofuran as a solvent.
- Standard polystyrene Standard polystyrene manufactured by Pressure Chemika Nore USA was used.
- An aluminum electrode pattern was formed on the obtained insulating film by a vapor deposition method to prepare a sample for measuring specific dielectric constant.
- the relative permittivity of the coating film at room temperature was measured at room temperature by a CV method at a frequency of 100 kHz using an HP16451B electrode and an HP4284A precision LCR meter manufactured by Yokogawa Hewlett-Packard Co., Ltd.
- the elastic modulus and the hardness were measured by a continuous rigidity measuring method using a nanoindenter XP (manufactured by Nano Instruments).
- a 400 nm SiO film is formed on the resulting insulating film by sputtering,
- the wafer was cut, a blank silicon wafer of the same size was bonded on the wafer piece using epoxy resin, and heated in an oven at 135 ° C. for 2 hours. This was cut into small pieces using a die sintering machine, and a peeling test was performed on each of them using a four-point bending adhesion measurement method. The results are shown below.
- A Adhesion energy of more than 3.0 joules per square meter
- the cross section of the insulating film is cut for observation by the focused ion beam method, and the The appearance was examined at 1: 1.
- the judgment result is shown as follows.
- the weight average molecular weight of the polymer (3) thus obtained was 860.
- reaction solution A had a weight average molecular weight of 27,000.
- the reaction solution A obtained in Example 1 was filtered through a Teflon (registered trademark) filter having a pore size of 0.2 ⁇ m to obtain a film-forming composition of the present invention.
- the substrate After applying the obtained composition to a silicon wafer by a spin coating method, the substrate was dried on a hot plate at 90 ° C. for 3 minutes, and then at 200 ° C. in a nitrogen atmosphere for 3 minutes, and further dried at 40 ° C. The substrate was baked on a hot plate for 60 minutes in a nitrogen atmosphere at 0 ° C.
- the insulating film obtained after firing (hereinafter referred to as “silica-based film”) was evaluated according to the evaluation method described in 5.1. Table 1 shows the evaluation results.
- a silica-based film was formed and evaluated in the same manner as in Example 4 except that reaction solutions B and C were used instead of reaction solution A in Example 4. Table 1 shows the evaluation results.
- a quartz separable flask was charged with 430 g of distilled ethanol, 211 g of ion-exchanged water, and 15.2 g of a 25% aqueous solution of tetramethylammonium-oxide at the mouth, and stirred uniformly.
- a mixture of 40.Og of methyltrimethoxysilane and 61.lg of tetraethoxysilane While maintaining this solution at 60 ° C., a reaction was performed for 2 hours. 300 g of propylene glycol monopropyl ether is added to this solution, and then the solution is concentrated to 20% (in terms of hydrolyzed condensate) using an evaporator at 50 ° C.
- reaction solution F 20 g of a 10% propylene glycol monopropyl ether solution was added to obtain a reaction solution F.
- a silica-based film was formed and evaluated in the same manner as in Example 4 except that this reaction solution F was used. Table 1 shows the evaluation results.
- Weight average molecular weight consisting of a repeating unit represented by the formula [Si (CH) (H) -CH]
- reaction solution I a 25% propylene glycol monopropyl ether solution of 000 polycarbosilane
- F a reaction solution of Comparative Example 2
- Example 4 A heat bake 0.50 2.53 9.1 0.9 AA
- Example 5 B heat bake 0.50 2.47 9.3 0.9 AA
- Example 6 C heat bake 0.50 2.91 9.6 1.0 AA
- Example 7 D heat bake 0.50 2.85 9.3 1.0 A ⁇ Comparative example 1
- a ⁇ Comparative Example 2 F Heating 0.50 2.86 7.2 0.7 BA Comparative Example 3
Abstract
Description
Claims
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EP05703611A EP1705206A4 (en) | 2004-01-16 | 2005-01-14 | PROCESS FOR PREPARING POLYMER, POLYMER, COMPOSITION FOR FORMING AN INSULATING FILM, PROCESS FOR PREPARING INSULATING FILM AND INSULATING FILM |
US11/484,604 US20070015892A1 (en) | 2004-01-16 | 2006-07-12 | Method for producing polymer, polymer, composition for forming insulating film, method for producing insulating film, and insulating film |
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JP2007324283A (ja) * | 2006-05-31 | 2007-12-13 | Jsr Corp | 絶縁膜形成用組成物およびその製造方法、ならびにシリカ系絶縁膜およびその形成方法 |
WO2007139004A1 (ja) * | 2006-05-31 | 2007-12-06 | Jsr Corporation | 絶縁膜形成用組成物およびその製造方法、ならびにシリカ系絶縁膜およびその形成方法 |
WO2008096656A1 (ja) * | 2007-02-07 | 2008-08-14 | Jsr Corporation | ケイ素含有ポリマーおよびその合成方法、膜形成用組成物、ならびにシリカ系膜およびその形成方法 |
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Also Published As
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JPWO2005068538A1 (ja) | 2007-12-27 |
TW200538490A (en) | 2005-12-01 |
JPWO2005068539A1 (ja) | 2007-12-27 |
EP1705207A1 (en) | 2006-09-27 |
JP5110243B2 (ja) | 2012-12-26 |
US7528207B2 (en) | 2009-05-05 |
EP1705207B1 (en) | 2012-10-24 |
EP1705206A4 (en) | 2009-06-24 |
US20070015892A1 (en) | 2007-01-18 |
TWI265172B (en) | 2006-11-01 |
WO2005068539A1 (ja) | 2005-07-28 |
KR20060123548A (ko) | 2006-12-01 |
US20070021580A1 (en) | 2007-01-25 |
EP1705206A1 (en) | 2006-09-27 |
TWI292349B (ja) | 2008-01-11 |
EP1705207A4 (en) | 2009-06-24 |
JP5013045B2 (ja) | 2012-08-29 |
KR101129875B1 (ko) | 2012-03-28 |
TW200536621A (en) | 2005-11-16 |
KR20060123549A (ko) | 2006-12-01 |
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