JP6131575B2 - 環状シロキサン化合物の製造方法およびジシロキサン化合物 - Google Patents
環状シロキサン化合物の製造方法およびジシロキサン化合物 Download PDFInfo
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- JP6131575B2 JP6131575B2 JP2012252735A JP2012252735A JP6131575B2 JP 6131575 B2 JP6131575 B2 JP 6131575B2 JP 2012252735 A JP2012252735 A JP 2012252735A JP 2012252735 A JP2012252735 A JP 2012252735A JP 6131575 B2 JP6131575 B2 JP 6131575B2
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- Japan
- Prior art keywords
- general formula
- divinyldisiloxane
- acid
- compound
- diisopropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 cyclic siloxane compound Chemical class 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000010408 film Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- SSJSQLFCGFXNDZ-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetra(propan-2-yl)-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound CC(C)[Si]1(C=C)O[Si](C(C)C)(C=C)O[Si](C(C)C)(C=C)O[Si](C(C)C)(C=C)O1 SSJSQLFCGFXNDZ-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 10
- ZOAUCLPLIFDWHD-UHFFFAOYSA-N O[Si](O[Si](C=C)(C(C)C)OC)(C=C)C(C)C Chemical compound O[Si](O[Si](C=C)(C(C)C)OC)(C=C)C(C)C ZOAUCLPLIFDWHD-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- MYIJOUFUSXNPJD-UHFFFAOYSA-N CO[Si](O[Si](C=C)(C(C)C)OC)(C=C)C(C)C Chemical compound CO[Si](O[Si](C=C)(C(C)C)OC)(C=C)C(C)C MYIJOUFUSXNPJD-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
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- 239000002243 precursor Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
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- 239000012159 carrier gas Substances 0.000 description 3
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- LTFFPRXIELHUGX-UHFFFAOYSA-N dimethoxy(3-methylbut-1-enyl)silane Chemical compound C(C)(C)C=C[SiH](OC)OC LTFFPRXIELHUGX-UHFFFAOYSA-N 0.000 description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BOHZRSRHHJHLHQ-UHFFFAOYSA-N 2,4,6-tris(ethenyl)-2,4,6-tri(propan-2-yl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound CC(C)[Si]1(C=C)O[Si](C(C)C)(C=C)O[Si](C(C)C)(C=C)O1 BOHZRSRHHJHLHQ-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 230000036962 time dependent Effects 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- JMROMRCGLWRYBP-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetraethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound CC[Si]1(C=C)O[Si](CC)(C=C)O[Si](CC)(C=C)O[Si](CC)(C=C)O1 JMROMRCGLWRYBP-UHFFFAOYSA-N 0.000 description 1
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
- IUXIKQGXIZRSBF-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetrapropyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound CCC[Si]1(C=C)O[Si](CCC)(C=C)O[Si](CCC)(C=C)O[Si](CCC)(C=C)O1 IUXIKQGXIZRSBF-UHFFFAOYSA-N 0.000 description 1
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- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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- RZUCEHQWIXHNJQ-UHFFFAOYSA-N 3,3-dipropoxyprop-1-enylsilane Chemical compound C(CC)OC(OCCC)C=C[SiH3] RZUCEHQWIXHNJQ-UHFFFAOYSA-N 0.000 description 1
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- MZZPECHJKDVTOI-UHFFFAOYSA-N 4,4-dimethoxybut-1-enylsilane Chemical compound COC(CC=C[SiH3])OC MZZPECHJKDVTOI-UHFFFAOYSA-N 0.000 description 1
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- UWKZJHALFALBFZ-UHFFFAOYSA-N diethoxy(3-methylbut-1-enyl)silane Chemical compound C(C)(C)C=C[SiH](OCC)OCC UWKZJHALFALBFZ-UHFFFAOYSA-N 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HPEASWRSAOKIDT-UHFFFAOYSA-N ethenyl-(ethenyl-ethoxy-methylsilyl)oxy-ethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)O[Si](C)(C=C)OCC HPEASWRSAOKIDT-UHFFFAOYSA-N 0.000 description 1
- HKGQTXCGPDIVTR-UHFFFAOYSA-N ethenyl-(ethenyl-hydroxy-methylsilyl)oxy-hydroxy-methylsilane Chemical compound C=C[Si](O)(C)O[Si](C)(O)C=C HKGQTXCGPDIVTR-UHFFFAOYSA-N 0.000 description 1
- SPCHDFGQKLHKIZ-UHFFFAOYSA-N ethenyl-(ethenyl-methoxy-methylsilyl)oxy-methoxy-methylsilane Chemical compound CO[Si](C)(C=C)O[Si](C)(OC)C=C SPCHDFGQKLHKIZ-UHFFFAOYSA-N 0.000 description 1
- PPWZUVSYOBJOHN-UHFFFAOYSA-N ethenyl-[ethenyl(propan-2-yl)silyl]oxy-propan-2-ylsilane Chemical compound CC(C)[SiH](C=C)O[SiH](C=C)C(C)C PPWZUVSYOBJOHN-UHFFFAOYSA-N 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
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- 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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
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- 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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- 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]
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Description
[1]下記一般式(1)
[2]一般式(1)で表されるジアルコキシアルキルビニルシラン化合物を酸または塩基の共存下、水と反応させる際の反応温度が−50〜25℃であることを特徴とする上述の[1]に記載の製造方法。
[3]一般式(2)で表されるジシロキサン化合物を酸または塩基の共存下、反応させる反応時間が30分(0.5時間)以上、1ヶ月(720時間)以下であることを特徴とする上述の[1]または[2]に記載の製造方法。
[4]酸として硫酸の共存下に反応を行うことを特徴とする上述の[1]〜[3]のいずれかに記載の製造方法。
[5]R1がイソプロピル基、R2がメチル基、R3およびR4がメチル基または水素原子であることを特徴とする上述の[1]〜[4]のいずれかに記載の製造方法。
[6]上述の[1]〜[5]のいずれかに記載の製造方法により製造された環状シロキサン化合物を材料として用いることを特徴とする絶縁膜。
[7]下記一般式(2)で表されることを特徴とするジシロキサン化合物。
以下、本発明をさらに詳細に説明する。
一般式(2)におけるR1は一般式(1)に同じであり、R3、R4は一般式(1)のR2に同じかまたは水素原子を示し、好ましくはR1がイソプロピル基、R3、R4はメチル基または水素原子である。
一般式(3)におけるR1は一般式(1)に同じであり、好ましくはR1がイソプロピル基である。
[1,3−ジアルコキシジシロキサンの合成]
不活性雰囲気下、攪拌装置、温度計を備えた100mLの3つ口フラスコに、ジメトキシイソプロピルビニルシラン(一般式(1)の化合物)5.0g(31.4mmol)とヘキサン25mlを仕込み、ドライアイス/エタノールにより内温を−15℃に冷却した。硫酸3.1g(31.4mmol)および水1.7g(94.4mmol)を、内温を−10℃以下に保ったまま滴下し、その後30分間撹拌し、目的の1,3−ジメトキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン、1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンおよび1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン(一般式(2)の化合物)が生成していることをGC/MS(EI)で確認した。反応液をGC/MS(EI)で分析した結果は以下の通りであった。
1,3−ジメトキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン(C12H26O3Si2) m/z:231(イソプロピル基脱離)、
1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン(C11H24O3Si2) m/z:217(イソプロピル基脱離)、
1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン(C10H22O3Si2) m/z:203(イソプロピル基脱離)
1,3−ジメトキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン、1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンおよび1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンは単離せず、次工程へ進んだ。
上記反応液を分層して水層を除去したのち、硫酸1.5g(0.16mol)を加え、還流条件で1時間撹拌した。反応終了後、硫酸層を除去し、得られた有機層を炭酸水素ナトリウム水溶液で中和し硫酸マグネシウムで乾燥した。ロータリーエバポレーターで溶媒留去したのち、減圧蒸留にて目的の2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサン(一般式(3)の化合物)が主成分(GC面積%:54.0%)の液体が2.6g(2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサンの収量:1.4g=2.6g×0.54)得られた。一般式(3)の化合物の収率は39.7%であった。この蒸留精製物をGC/MS(EI)で分析した結果は以下の通りであった。
(比較例1)
実施例1において、シクロテトラシロキサンの合成工程で分層・水層除去作業を行わないこと以外は、実施例1と同様の実験を行った。蒸留精製物(液体)は、収量2.6g、目的の2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサンは、GC面積%が2.4%であり、極微量しか(2.6g×0.024=0.062g、収率1.7%)生成しなかった。
[シクロテトラシロキサン選択率の向上]
実施例1において、シクロテトラシロキサンの合成工程での反応を、還流条件で6時間撹拌に変更した以外は、実施例1と同様の実験を行った。目的の2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサンへの転換率の経時変化をGC分析により確認した。反応終了後、実施例1と同様に処理を行った。一般式(3)の化合物の収率は69.2%であった。結果を図1および図2に示す。
[シクロテトラシロキサン選択率の向上、室温(25℃)1ヶ月(720時間)]
実施例1において、シクロテトラシロキサンの合成工程での反応を、還流条件で30分撹拌後さらに室温で1ヶ月撹拌に変更した以外は、実施例1と同様の実験を行った。目的の2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサンへの転換率の経時変化をGC分析により確認した。反応終了後、実施例1と同様に処理を行った。一般式(3)の化合物の収率は77.0%であった。結果を図3および図4に示す。
[2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサンを用いた絶縁膜の製造]
実施例1で得た2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサン(一般式(3)の化合物)が主成分の液体を蒸留精製した2,4,6,8−テトライソプロピル−2,4,6,8−テトラビニルシクロテトラシロキサンを原料として、図5の装置を用いて、原料温度120℃、キャリアガス(He)流量100sccm、原料容器内圧力22Torr、基板温度150℃、反応室内圧力100Paで、電源周波数13.56MHzのRF電源の出力を25Wに設定したPECVD法により、Si基板上に2分成膜を行った。成膜した絶縁膜について日本分光株式会社製のエリプソメーター(型式:MEL−30S)を用いて膜厚を測定したところ約150nmであった。この絶縁膜上に、アルミ電極を蒸着法によって成膜した後、Agilent社製の4284AプレシジョンLCRメータにより25℃、周波数1kHzの静電容量と誘電損失を測定し、比誘電率を計算したところ、k 2.69、tanδ=0.0004であった。測定部分の誘電体の面積は1.01×10−8m2であった。また、直流電流+40Vの条件でのリーク電流を測定したところ、8.8×10−10A/cm2の電流密度であった。
[1,3−ジメトキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン、1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンおよび1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンの合成]
不活性雰囲気下、攪拌装置、温度計を備えた200mLの3つ口フラスコに、ジメトキシイソプロピルビニルシラン15.0g(93.6mmol)、ヘキサン90mlを仕込み、ドライアイス/エタノールにより内温を−20℃に冷却した。硫酸0.97g(9.9mmol)を添加し、水3.51g(195mmol)を内温−15℃以下に保ち30分かけて滴下した。内温を−10℃に保持したまま5時間撹拌後、トリエチルアミン2.7g(26.7mmol)を添加し、水層を除去し有機層を硫酸マグネシウムで乾燥した。ろ過後、ロータリーエバポレーターで溶媒留去したのち、減圧蒸留にて目的の1,3−ジメトキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン、1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンおよび1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンの混合物である液体2.7gが得られた。この混合物をシリカゲルカラムクロマトグラフィー(溶出溶媒:ヘキサン/酢酸エチル=9/1)により精製し、目的化合物である1,3−ジメトキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンを0.51g、収率4.0%、1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンを1.78g、収率14.6%、1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサンを0.31g、収率2.7%で得た。それぞれの化合物をGC/MS(EI)(図6−8)および1H−NMRで分析した結果は以下の通りであった。
1,3−ジメトキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン(C12H26O3Si2) m/z:231(イソプロピル基脱離)
1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン(C11H24O3Si2) m/z:217(イソプロピル基脱離)
1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン(C10H22O3Si2) m/z:203(イソプロピル基脱離)
1H−NMR(500MHz,CDCl3,δppm)
1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン
6.13−5.92(m,6H)、3.53(s,6H)、1.01(d,J=6.5Hz,12H)、0.94−0.87(m,2H)
1−メトキシ−3−ヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン
6.13−5.90(m,6H)、3.52(s,3H)、2.31(s,1H)、1.00(dd,J=6Hz,J=2.5Hz,6H)、1.03(d,J=6Hz,6H)、0.96−0.88(m,2H)
1,3−ジヒドロキシ−1,3−ジイソプロピル−1,3−ジビニルジシロキサン
6.10−5.91(m,6H)、2.40(s,2H)、1.01(d,J=7.5Hz,12H)、0.97−0.89(m,2H)
(参考例1)
[2,4,6−トリイソプロピル−2,4,6−トリビニルシクロトリシロキサンを用いた絶縁膜の製造]
2,4,6−トリイソプロピル−2,4,6−トリビニルシクロトリシロキサンを原料として、図5の装置を用いて、原料温度83℃、キャリアガス(He)流量100sccm、原料容器内圧力22Torr、基板温度150℃、反応室内圧力100Paで、電源周波数13.56MHzのRF電源の出力を25Wに設定したPECVD法により、Si基板上に3分成膜を行った。成膜した絶縁膜について日本分光株式会社製のエリプソメーター(型式:MEL−30S)を用いて膜厚を測定したところ約210nmであった。この絶縁膜上に、アルミ電極を蒸着法によって成膜した後、Agilent社製の4284AプレシジョンLCRメータにより25℃、周波数1kHzの静電容量と誘電損失を測定し、比誘電率を計算したところ、k 2.74、tanδ=0.01であった。測定部分の誘電体の面積は9.88×10−7m2であった。また、直流電流+40Vの条件でのリーク電流を測定したところ、2.0×10−9A/cm2の電流密度であった。
2.基板
3.上部電極
4.下部電極
5.恒温槽
6.原料容器
7.真空ポンプ
8.マッチング回路
9.RF電源
10.アース
11.ヒーター
12.マスフローコントローラー
13.ヘリウムガス
Claims (5)
- 一般式(1)で表されるジアルコキシアルキルビニルシラン化合物を酸または塩基の共存下、水と反応させる際の反応温度が−50〜25℃であることを特徴とする請求項1に記載の製造方法。
- 一般式(2)で表されるジシロキサン化合物を酸または塩基の共存下、反応させる反応時間が30分(0.5時間)以上、1ヶ月(720時間)以下であることを特徴とする請求項1又は2に記載の製造方法。
- 酸として硫酸の共存下に反応を行うことを特徴とする請求項1〜3のいずれかに記載の製造方法。
- R1がイソプロピル基、R2がメチル基、R3およびR4がメチル基または水素原子であることを特徴とする請求項1〜4のいずれかに記載の製造方法。
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