CN112110948A - Preparation method of liquid diamino-substituted disilane and application of liquid diamino-substituted disilane product - Google Patents
Preparation method of liquid diamino-substituted disilane and application of liquid diamino-substituted disilane product Download PDFInfo
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- diamino
- disilane
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- -1 diamino-substituted disilane Chemical class 0.000 title claims abstract description 30
- 239000007788 liquid Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000047 product Substances 0.000 claims abstract description 33
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 20
- 239000012043 crude product Substances 0.000 claims abstract description 17
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 17
- VYFXMIAQVGXIIN-UHFFFAOYSA-N trichloro(chlorosilyl)silane Chemical class Cl[SiH2][Si](Cl)(Cl)Cl VYFXMIAQVGXIIN-UHFFFAOYSA-N 0.000 claims abstract description 17
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001914 filtration Methods 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 13
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical class [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 239000011261 inert gas Substances 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 20
- 229940043279 diisopropylamine Drugs 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 13
- 238000000231 atomic layer deposition Methods 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
- 239000012448 Lithium borohydride Substances 0.000 claims description 6
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004914 cyclooctane Substances 0.000 claims description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 230000008021 deposition Effects 0.000 abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 238000000151 deposition Methods 0.000 description 19
- 239000007787 solid Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 13
- 239000010408 film Substances 0.000 description 11
- 229910010084 LiAlH4 Inorganic materials 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 229910052681 coesite Inorganic materials 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229910052906 cristobalite Inorganic materials 0.000 description 9
- 229910052744 lithium Inorganic materials 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 229910052682 stishovite Inorganic materials 0.000 description 9
- 229910052905 tridymite Inorganic materials 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- ZLCPPOATHNIRAQ-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-silylsilyl]-N-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)[SiH]([SiH3])N(C(C)C)C(C)C ZLCPPOATHNIRAQ-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910008045 Si-Si Inorganic materials 0.000 description 4
- 229910006411 Si—Si Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005137 deposition process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VYIRVGYSUZPNLF-UHFFFAOYSA-N n-(tert-butylamino)silyl-2-methylpropan-2-amine Chemical compound CC(C)(C)N[SiH2]NC(C)(C)C VYIRVGYSUZPNLF-UHFFFAOYSA-N 0.000 description 2
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000013341 scale-up Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000000427 thin-film deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JVNJBCRZXBFQMH-UHFFFAOYSA-N C(C)(C)(C)N(C(C)(C)C)[SiH]([SiH3])N(C(C)(C)C)C(C)(C)C Chemical compound C(C)(C)(C)N(C(C)(C)C)[SiH]([SiH3])N(C(C)(C)C)C(C)(C)C JVNJBCRZXBFQMH-UHFFFAOYSA-N 0.000 description 1
- JMFFCOFUIBUIHG-UHFFFAOYSA-N CCC(C)N(C(C)CC)[SiH]([SiH3])N(C(C)CC)C(C)CC Chemical compound CCC(C)N(C(C)CC)[SiH]([SiH3])N(C(C)CC)C(C)CC JMFFCOFUIBUIHG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BIVNKSDKIFWKFA-UHFFFAOYSA-N N-propan-2-yl-N-silylpropan-2-amine Chemical compound CC(C)N([SiH3])C(C)C BIVNKSDKIFWKFA-UHFFFAOYSA-N 0.000 description 1
- WLSVLQJPKZNQJC-UHFFFAOYSA-N N-propan-2-ylpropan-2-amine silane Chemical compound [SiH4].C(C)(C)NC(C)C WLSVLQJPKZNQJC-UHFFFAOYSA-N 0.000 description 1
- 229910007991 Si-N Inorganic materials 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006294 Si—N Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OWKFQWAGPHVFRF-UHFFFAOYSA-N n-(diethylaminosilyl)-n-ethylethanamine Chemical compound CCN(CC)[SiH2]N(CC)CC OWKFQWAGPHVFRF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- GIRKRMUMWJFNRI-UHFFFAOYSA-N tris(dimethylamino)silicon Chemical compound CN(C)[Si](N(C)C)N(C)C GIRKRMUMWJFNRI-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/40—Oxides
- C23C16/401—Oxides containing silicon
- C23C16/402—Silicon dioxide
-
- 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
- C23C16/44—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 method of coating
- C23C16/455—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 method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
- C23C16/45523—Pulsed gas flow or change of composition over time
- C23C16/45525—Atomic layer deposition [ALD]
- C23C16/45553—Atomic layer deposition [ALD] characterized by the use of precursors specially adapted for ALD
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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Abstract
The invention provides a preparation method of liquid diamino substituted disilane and application of a product thereof in film ALD deposition. Adding a nonpolar solvent and hexachlorodisilane into a reaction container under the protection of inert gas, cooling to-20 ℃ and below, adding monosubstituted organic amine, filtering and distilling after reaction to obtain a diamino-substituted tetrachlorodisilane intermediate, mixing with tetrahydrofuran, cooling to-40 ℃ and below, dripping a tetrahydrofuran solution containing a reducing agent into the system for reduction, slowly heating the system to room temperature after dripping is finished, continuously stirring, extracting by using the nonpolar solvent, concentrating and distilling the extraction solution to obtain a crude product with the purity of more than or equal to 99%, and rectifying and purifying to obtain the liquid diamino-substituted disilane with the purity of more than or equal to 7N.
Description
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of semiconductors, and particularly relates to a preparation method of liquid diamino substituted disilane for thin film deposition and application of a product of the liquid diamino substituted disilane.
[ background of the invention ]
SiO2Since the thin film is easily obtained by oxidation of a Si substrate, and has good chemical, mechanical, dielectric properties and suitable bandwidth, etc., it has been widely studied and applied in the semiconductor field. In SiO2In the thin film preparation technology, the atomic-level thickness can be controlled, the large-area uniform coverage can be realized, the quality of the thin film is high and the like by the self-limiting ALD, and the preparation technology is the most widely applied preparation technology at present.
In the ALD production process, the choice of precursor is very important. Currently, common precursor materials for depositing SiO2 thin films by ALD are bis (diethylamino) silane (BDEAS), bis (tert-butylamino) silane (BTBAS), tris (dimethylamino) silane (3DMAS), diisopropylamine silane (DIPAS), and the like. However, the deposition rates of these precursor materials are relatively limited, such as: BDEAS, 3DMAS, DIPAS oxidized by oxygen plasma at 200 ℃ at deposition rates of: 0.70, 1.10, 1.20A/cycle; BDEAS and DIPAS respectively have deposition rates of 0.36 and 1.20A/cycle at 300 ℃ and ozone as an oxidant.
As the thickness of portions of the film increases, some process flows require higher deposition rates to improve production efficiency, and therefore there is a need to develop new precursor materials with higher deposition rates.
SiO has been deposited at high deposition rates2The film direction has been studied comparatively much. Such as WO2011042882a 2: high displacement rate of SiO2The use of the chemical layer deposition at an extra low temperature, wherein silane and disilane containing chlorine are used as silicon source, and ozone, water or oxygen plasma is used as oxidant, so that SiO can be deposited at 50-200 deg.C2The deposition rate of the film can reach 2A/cycle. However, the generated HCl has strong corrosivity to the cavity and the pipeline, so that the requirement on equipment is high, and a small amount of Cl element remains in the film.
Further examples are US20180127592a 1: the inventors have designed disiloxane, trisiloxane, and other structures that can significantly enhance SiO at high temperatures2The deposition rate. However, the siloxane structure is not suitable for low-temperature SiO due to its low molecular activity2And (5) depositing a thin film.
[ summary of the invention ]
The invention provides a preparation method of liquid diamino substituted disilane, which can obtain liquid SiO at normal temperature and is suitable for high deposition rate ALD2A precursor of the thin film.
The invention also provides the application of the product in the ALD deposition of the thin film.
The technical solution of the invention is as follows:
a preparation method of liquid diamino substituted disilane is characterized by comprising the following steps:
1) under the protection of inert gas, adding a non-polar solvent and hexachlorodisilane into a reaction vessel, cooling to-20 ℃ or below, adding mono-substituted organic amine, filtering after reaction, and distilling to obtain a diamino-substituted tetrachlorodisilane intermediate;
2) under the protection of inert gas, mixing a diamino-substituted tetrachlorodisilane intermediate with tetrahydrofuran, cooling to-40 ℃ and below, dripping a tetrahydrofuran solution containing a reducing agent into the system for reduction, slowly heating the system to room temperature after finishing dripping, and continuously stirring; the reducing agent is lithium aluminum hydride (LiAlH)4) Lithium borohydride (LiBH)4) Mixtures of sodium borohydride and sodium hydride (NaBH)4+ NaH);
3) extracting the system in the step 2) by using a non-polar solvent, concentrating and distilling the extraction solution to obtain a crude product with the purity of more than or equal to 99%;
4) rectifying and purifying the crude product obtained in the step 3) to obtain liquid diamino substituted disilane with the purity more than or equal to 7N.
Further, the mono-substituted organic amine of the step 1) includes at least one of diisopropylamine, di-sec-butylamine, and tert-butylamine.
Further, the concentration of the reducing agent in the tetrahydrofuran solution containing the reducing agent in the step 2) is 1.0 to 2.5 mol/L.
Further, the nonpolar solvent includes at least one of n-hexane, n-pentane, n-heptane, toluene, cyclohexane, and cyclooctane.
Further, the volume ratio of the nonpolar solvent in the step 1) to the hexachlorodisilane is 5: 1-20: 1; preferably, the volume ratio of the nonpolar solvent to the hexachlorodisilane is 5: 1-10: 1, so that the hexachlorodisilane and the solvent can be fully mixed, the heat is uniformly released, the solvent is not wasted due to excessive dilution, and the concentration time is too long.
Further, the volume ratio of the diamino-substituted tetrachlorodisilane intermediate in the step 2) to tetrahydrofuran is 1: 1-10: 1; preferably, the volume ratio of the two is 2: 1-5: 1.
The other technical scheme of the invention is the application of the product, which is characterized in that liquid diamino substituted disilane with the purity more than or equal to 7N is used as a precursor for the atomic layer deposition of the film.
Compared with the prior art, the invention has the following beneficial effects:
(1) the product obtained by the invention is liquid at normal temperature, and the liquid product is easier to purify and transport than the solid product, and is more suitable for SiO2The ALD film deposition process can obviously improve SiO2The deposition rate of the film.
(2) The invention can easily realize the purpose of purification, adopts non-polar solvent (such as normal hexane, pentane, heptane, toluene and the like) for extraction, separates the product from inorganic salt (lithium chloride, aluminum chloride and the like) generated by reduction, abandons the common filtering step and is beneficial to the rectification and purification of the product.
(3) The method has the advantages of few byproducts, high yield and high safety. If in solid LiAlH4Is a reducing agent, glycol dimethyl ether is used as a solvent, and LiAlH is added in a polyether system4The stronger reducibility is embodied, and the reaction is not easy to control. Solid LiAlH4Can not be dispersed in the system very uniformly, is not favorable for scale-up production, and is solid LiAlH4The reduction system with ethylene glycol dimethyl ether can cause excessive local reducing agent, destroy Si-Si bonds in the product and form monosubstituted silane, and the monosubstituted silane can be further reduced into SiH4Releasing pyrophoric gas; the invention uses tetrahydrofuran as solvent and contains reducing agent LiAlH4、LiBH4Or NaBH4The solution of the NaH is added into the reaction system, so that the reaction is milder, the control is easier, and the yield is higher.
[ description of the drawings ]
FIG. 1 is a structural diagram of a bis (diisopropylamino) disilane molecule;
FIG. 2 is a reaction scheme for preparing bis (diisopropylamino) disilane according to the present invention;
FIG. 3 is a nuclear magnetic spectrum of the product of example one;
FIG. 4 is an ICP-MS screenshot of the product of the first embodiment;
FIG. 5 is a comparison of the reaction system of comparative example I and the reaction system of example I with BDIPADS and DIPAS gas chromatograms (the curves from top to bottom in the figure correspond to the reaction system of comparative example I, the reaction system of example I, BDIPADS and DIPAS in sequence);
FIG. 6 is a screenshot of ICP-MS of the product of comparative example two.
[ detailed description ] embodiments
The present invention will be described in further detail with reference to the following examples, but the present invention is not limited to the following examples.
The general formula of the diamino-substituted disilane can be written as: r1R2N-SiH2-SiH2-NR3R4Wherein R1-4 can be H or C1-6 straight chain or branched chain structure. The preparation process comprises the following steps:
1) under the protection of inert gas, adding a non-polar solvent and hexachlorodisilane into a reaction vessel, cooling to-20 ℃, adding mono-substituted organic amine, filtering and distilling after reaction to obtain a diamino-substituted tetrachlorodisilane intermediate; the nonpolar solvent can be selected from one of n-hexane, n-pentane, n-heptane, toluene, cyclohexane or cyclooctane, the volume ratio of the nonpolar solvent to hexachlorodisilane is preferably 5: 1-10: 1, and the monosubstituted organic amine can be selected from one of diisopropylamine, di-sec-butylamine and tert-butylamine;
2) under the protection of inert gas, bis-amino substituted tetrachlorodisilaneMixing the intermediate with tetrahydrofuran, cooling to-60 ℃, then dripping a tetrahydrofuran solution containing a reducing agent into the system for reduction, slowly heating the system to room temperature after finishing dripping, and continuously stirring; the reducing agent is preferably LiAlH4、LiBH4Or NaBH4+ NaH, the concentration of the tetrahydrofuran solution of the reducing agent is preferably 1.0-2.5 mol/L, and the ratio of the diamino-substituted tetrachlorodisilane intermediate to tetrahydrofuran is preferably 2: 1-5: 1;
3) extracting the system in the step 2) by using a non-polar solvent, concentrating and distilling the extraction solution to obtain a crude product with the purity of more than or equal to 99%;
4) rectifying and purifying the crude product obtained in the step 3) to obtain liquid diamino substituted disilane with the purity not less than 7N.
The product obtained by the process is liquid-state diamino-substituted disilane with purity more than or equal to 7N at normal temperature, is easier to purify and transport than a solid product, and is more suitable for SiO2The ALD film deposition process can obviously improve SiO2The deposition rate of the film.
The invention also has higher purity and yield.
A representative bis (diisopropylamino) disilane product, bis (diisopropylamino) disilane, is exemplified by 1,2-bis (diacetylpyramine) disilane, BDIPADS, which has the structure shown in FIG. 1, and the overall reaction sequence according to the present invention is shown in FIG. 2. For comparison, we prepared BDIPADS according to the publication "Disilanyl-amines-compounds comprising the structural unit Si-Si-N, as single-source condensers for plasma-enhanced chemical vapor deposition (PE-CVD) of silicon nitride [ J ]. ZChrrift F ü r Anorganische Und Allgene Chemie,1993,619(8):1347 and 1352".
Compared with the two, the invention also has the advantages that:
the invention is easier to realize the purpose of purification, adopts non-polar solvent (such as normal hexane, pentane, heptane, toluene and the like) for extraction, separates the product from inorganic salt (lithium chloride, aluminum chloride and the like) generated by reduction, abandons the filtration step and is beneficial to the rectification and purification of the product. If the method reported in the above literature is used for filtration, firstly, inorganic salts such as aluminum chloride and the like generated by the reduction reaction are viscous, the filtration efficiency is very low, and the product is difficult to separate; and secondly, Li and Al metal impurities in the product are difficult to remove. Under the same rectification conditions, the content of Li and Al in the product obtained by the method can be reduced to below 0.01 ppm; in the reported route, more than 1ppm of Li and Al still exist.
② the invention has less by-products, high yield and high safety. The above reported literature uses solid LiAlH4As a reducing agent, ethylene glycol dimethyl ether is used as a solvent. In the case of polyether systems, LiAlH4The stronger reducibility is embodied, and the reaction is not easy to control. Solid LiAlH4Cannot be dispersed in the system very uniformly, and is not favorable for scale-up production. Solid LiAlH4The reduction system with ethylene glycol dicarbamidine can cause excessive local reducing agent, destroy Si-Si bonds in the product and form monosubstituted silane, and may further reduce the Si-Si bonds to SiH4And self-ignitable gases are evolved. In the invention, tetrahydrofuran is used as a solvent, and LiAlH is used4The solution is added into a reaction system, so that the reaction is milder and is easier to control. The yield is also higher. According to the ratio reported in the literature, the yield of more than 80% (only 57% is reported) can be obtained in the invention. The reason for this is probably that the reducing agent LiAlH4After the increase, Si-Si bonds are broken to produce monosubstituted silanes of ammonia, reducing the yield. Similarly, with solid LiBH4Or NaBH4+ NaH as reducing agent also has a similar effect.
The following examples are not provided to limit the scope of the present invention, nor are the steps described to limit the order of execution, and the directions described are limited to the drawings. The yield in this context is an actual weight which is obvious improvement for the person skilled in the art in combination with the prior general knowledge and falls within the scope of the claimed invention.
Example one
Under the protection of nitrogen, 3L of n-hexane and 300g of Hexachlorodisilane (HCDS) are added into a 5L reaction bottle, the temperature is reduced to-20 ℃, 500g of Diisopropylamine (DIPA) is slowly dripped, and the system temperature is maintained between-10 ℃ and-20 ℃. After the reaction was completed, filtration was performed, the solid was washed with 1L of n-hexane, the filtrates were combined and distilled to separate the diisopropylamine-substituted tetrachlorodisilane intermediate, and 403g was weighed. Mixing the obtained bis-diisopropylamine substituted tetrachlorodisilane intermediate with 1.5L Tetrahydrofuran (THF) in a nitrogen atmosphere, cooling the system to-60 ℃, and slowly dropping 450mL tetrahydrofuran solution (2.5mol/L) of lithium aluminum hydride into the system for reduction. After the addition was complete, the system was slowly warmed to room temperature and stirred continuously. Stirring overnight, extracting with dehydrated n-hexane under nitrogen protection, concentrating the extractive solution, and distilling to obtain coarse product 235g with purity of 99% or more and yield of 81%; and rectifying and purifying the crude product to obtain a product with the purity of more than 7N.
Of products1The H NMR spectrum is shown in FIG. 3, the chemical shift at 1.08 is H of methyl on isopropyl, and the number of H is 24; the chemical shift at 3.05 is H on-CH-on isopropyl, and the number of H is 4; chemical shift at 4.93 is-SiH2H on-is 4 in number. The product was thus demonstrated to be bis (diisopropylamino) disilane (BDIPADS).
The ICP-MS measurement screenshot of the metal content in the product is shown in FIG. 4, and the content of Li and Al metal ions in the obtained sample is respectively 1ppt level and 10ppt level. The actual content of Li and Al metal ions obtained by calculation is about 0.1ppb and 1ppb, the purity of the product reaches more than 7N, and the situation that the Li and Al elements in the product are too high is avoided.
Comparative example 1
Under the protection of nitrogen, 3L of n-hexane and 300g of HCDS are added into a 5L reaction bottle, the temperature is reduced to-20 ℃, 500g of DIPA is slowly dripped, and the temperature of the system is maintained between-10 ℃ and-20 ℃. After the reaction, filtering, cleaning the solid with 1L of n-hexane, combining the filtrates, distilling, separating the bis-diisopropylamine substituted tetrachlorodisilane intermediate, mixing with 1.5L of THF under nitrogen atmosphere, cooling the system to-60 ℃, and slowly dropping 450mL of tetrahydrofuran solution (2.5mol/L) of lithium aluminum hydride into the system for reduction. After the completion of the dropwise addition, 20mL of a tetrahydrofuran solution of lithium aluminum hydride (2.5mol/L) was further added to the system. The system was slowly warmed to room temperature and stirred continuously. After stirring overnight, extraction was carried out with n-hexane which had been freed of water under nitrogen.
The extracted reaction solution was subjected to a Gas Chromatography (GC) test and compared with the reaction system of example one (without additional addition of lithium aluminum hydride) under the same conditions, pure BDIPADS and pure DIPAS (diisopropylaminosilane, prepared according to the method described in patent CN 104876957B), and the results are shown in fig. 5. From the comparison, it is known that the first comparative example produces more DIPAS and the first example produces more BDIPADS, that is, an excessive amount of reducing agent (lithium aluminum hydride) causes Si — Si bond cleavage to produce DIPAS, which lowers the yield.
Comparative example No. two
Under the protection of nitrogen, 3L of n-hexane and 300g of HCDS are added into a 5L reaction bottle, the temperature is reduced to-20 ℃, 500g of DIPA is slowly dripped, and the temperature of the system is maintained between-10 ℃ and-20 ℃. After the reaction, filtering, cleaning the solid with 1L of n-hexane, combining the filtrates, distilling, separating the bis-diisopropylamine substituted tetrachlorodisilane intermediate, mixing with 1.5L of THF under nitrogen atmosphere, cooling the system to-60 ℃, and slowly dropping 450mL of tetrahydrofuran solution (2.5mol/L) of lithium aluminum hydride into the system for reduction. After the addition was complete, the system was slowly warmed to room temperature and stirred continuously. After stirring overnight, settling, suction filtration and washing. Because the aluminum chloride generated in the reaction process is viscous, the filtering efficiency is greatly slowed down. The suction filtration and washing process lasts about 10 hours, and compared with the 3-hour extraction process, the efficiency is greatly reduced. Concentrating and distilling the filtrate to obtain 220g of crude product with the purity of more than or equal to 99 percent and the yield of 76 percent; then purifying by the same rectifying column and rectifying method.
The ICP-MS measurement of the metal content of the product of the second comparative example is shown in FIG. 6, and the Li and Al metal ion contents of the obtained sample are measured to be 20ppt grade and 300ppt grade, respectively. The actual content of Li and Al metal ions obtained by calculation is about 2ppb and 30ppb, which shows that the content of Li and Al elements in the product is higher. Comparison of example one with comparative example two shows that the extraction-concentration-distillation-rectification process of the present invention has significant yield and purity advantages over conventional filtration-concentration-distillation-rectification, and the product purity of the present invention is much higher than that of comparative example two.
Example two
Under the protection of nitrogen, 2L of n-pentane and 150g of Hexachlorodisilane (HCDS) are added into a 3L reaction bottle, the temperature is reduced to-30 ℃, 320g of Di-sec-butylamine (Di-sec-butyl amine) is slowly added dropwise, and the system temperature is maintained between-10 ℃ and-20 ℃. After the reaction was completed, the solid was filtered, washed with 500mL of n-pentane, the filtrates were combined and distilled to separate the bis-di-sec-butylamine substituted tetrachlorodisilane intermediate, which was weighed to 213 g. The di-sec-butylamine substituted tetrachlorodisilane intermediate is mixed with 1L Tetrahydrofuran (THF) in nitrogen atmosphere, the temperature is reduced to-40 ℃, and 550mL tetrahydrofuran solution (1.0mol/L) of lithium aluminum hydride is slowly dropped into the system for reduction. After the addition was complete, the system was slowly warmed to room temperature and stirred continuously. Stirring overnight, extracting with dehydrated n-hexane under nitrogen protection, concentrating the extractive solution, and distilling to obtain crude product 132g with purity of 99% or more and yield of 82%. And rectifying and purifying the crude product to obtain the bis (di-sec-butylamino) disilane with electronic grade purity.
EXAMPLE III
Under the protection of nitrogen, 500mL of toluene and 50g of Hexachlorodisilane (HCDS) are added into a 1L reaction bottle, the temperature is reduced to-30 ℃, 55g of di-tert-butylamine is slowly added dropwise, and the temperature of the system is maintained between-10 ℃ and-20 ℃. After the reaction was completed, the solid was filtered, washed with 200mL of toluene, the filtrates were combined and distilled to separate the di-tert-butylamine-substituted tetrachlorodisilane intermediate, which was weighed to 57 g. The di-tert-butylamine substituted tetrachlorodisilane intermediate is mixed with 1L Tetrahydrofuran (THF) in nitrogen atmosphere, the temperature is reduced to-60 ℃, and 75mL tetrahydrofuran solution (2.5mol/L) of lithium aluminum hydride is slowly dropped into the system for reduction. After the addition was complete, the system was slowly warmed to room temperature and stirred continuously. Stirring overnight, extracting with dehydrated toluene under nitrogen protection, concentrating the extractive solution, and distilling to obtain crude product with purity of not less than 99% 30.0g and yield of 80%. And rectifying and purifying the crude product to obtain the bis (di-tert-butylamino) disilane with electronic grade purity.
Example four
Under the protection of nitrogen, 3L of n-hexane and 300g of Hexachlorodisilane (HCDS) are added into a 5L reaction bottle, the temperature is reduced to-20 ℃, 500g of Diisopropylamine (DIPA) is slowly dripped, and the system temperature is maintained between-10 ℃ and-20 ℃. After the reaction was completed, filtration was performed, the solid was washed with 1L of n-hexane, the filtrates were combined and distilled to separate the diisopropylamine-substituted tetrachlorodisilane intermediate, and 405g was weighed. Mixing the obtained bis-diisopropylamine substituted tetrachlorodisilane intermediate with 1.5L Tetrahydrofuran (THF) in nitrogen atmosphere, cooling the system to-60 deg.C, and slowly dropping 750mL lithium borohydride (LiBH)4) Then the solution (1.5mol/L) of tetrahydrofuran was subjected to reduction. After the addition was complete, the system was slowly warmed to room temperature and stirred continuously. Stirring overnight, extracting with dehydrated n-hexane under nitrogen protection, concentrating the extractive solution, and distilling to obtain crude product 229g with purity of 99% or more and yield of 79%; and rectifying and purifying the crude product to obtain a product with the purity of more than 7N.
EXAMPLE five
Under the protection of nitrogen, 3L of n-hexane and 300g of Hexachlorodisilane (HCDS) are added into a 5L reaction bottle, the temperature is reduced to-20 ℃, 500g of Diisopropylamine (DIPA) is slowly dripped, and the system temperature is maintained between-10 ℃ and-20 ℃. After the reaction was completed, filtration was performed, the solid was washed with 1L of n-hexane, the filtrates were combined and distilled to separate the diisopropylamine-substituted tetrachlorodisilane intermediate, and 400g was weighed. Mixing the obtained bis-diisopropylamine substituted tetrachlorodisilane intermediate with 1.5L Tetrahydrofuran (THF) in nitrogen atmosphere, cooling the system to-60 deg.C, and slowly dropping 2000mL NaH in tetrahydrofuran solution (2.5mol/L, containing catalytic amount of NaBH)40.1mol/L) was used. After the addition was complete, the system was slowly warmed to room temperature and stirred continuously. Stirring overnight, extracting with dehydrated n-hexane under nitrogen protection,the extraction solution is concentrated and distilled to obtain 230g of crude product with the purity of more than or equal to 99 percent, and the yield is 79 percent; and rectifying and purifying the crude product to obtain a product with the purity of more than 7N.
PEALD SiO2Thin film deposition test:
BDIPADS and DIPAS obtained in example one (prepared according to the method described in patent CN104876957B and purified to>99.99999%) under the same conditions2Depositing a thin film, wherein the specific process is as follows:
1. the substrate was heated to 200 ℃.
2. Precursor material (BDIPADS or DIPAS) is fed into the ALD chamber by means of vapor pumping.
3. And after the precursor molecules form chemical adsorption on the surface of the substrate or the device, pumping out the redundant reaction source, and purging with argon.
4. And introducing oxygen into the cavity, and lighting the plasma with the plasma power of 300W. After the reaction was completed, excess gas was evacuated and purged with argon.
5. And (4) circulating the steps 1-4 for 200 deposition cycles, and measuring the obtained film.
SiO deposited by BDIPAS and DIPAS as precursors2The films, having thicknesses of 366A and 242A, respectively, correspond to deposition rates of 1.83A/cycle and 1.21A/cycle. It can be seen that SiO is deposited by PEALD at 200 deg.C2The deposition rate of BDIPADS is improved by more than 50% compared with that of DIPAS.
Claims (7)
1. A preparation method of liquid diamino substituted disilane is characterized by comprising the following steps:
1) under the protection of inert gas, adding a non-polar solvent and hexachlorodisilane into a reaction vessel, cooling to-20 ℃ or below, adding mono-substituted organic amine, filtering after reaction, and distilling to obtain a diamino-substituted tetrachlorodisilane intermediate;
2) under the protection of inert gas, mixing a diamino-substituted tetrachlorodisilane intermediate with tetrahydrofuran, cooling to-40 ℃ and below, dripping a tetrahydrofuran solution containing a reducing agent into the system for reduction, slowly heating the system to room temperature after finishing dripping, and continuously stirring; the reducing agent is any one of lithium aluminum hydride, lithium borohydride, a mixture of sodium borohydride and sodium hydride;
3) extracting the system in the step 2) by using a non-polar solvent, concentrating and distilling the extraction solution to obtain a crude product with the purity of more than or equal to 99%;
4) rectifying and purifying the crude product obtained in the step 3) to obtain liquid diamino substituted disilane with the purity more than or equal to 7N.
2. The process of claim 1, wherein the mono-substituted organic amine of step 1) comprises at least one of diisopropylamine, di-sec-butylamine, and tert-butylamine.
3. The method for preparing liquid diamino-substituted disilane according to claim 1, wherein the concentration of the reducing agent in the tetrahydrofuran solution containing the reducing agent in step 2) is 1.0-2.5 mol/L.
4. The method of claim 1, wherein the non-polar solvent comprises at least one of n-hexane, n-pentane, n-heptane, toluene, cyclohexane, and cyclooctane.
5. The method for preparing liquid diamino-substituted disilane according to claim 1, wherein the volume ratio of the nonpolar solvent and the hexachlorodisilane in the step 1) is 5: 1-20: 1.
6. The method for preparing liquid diamino-substituted disilane according to claim 1, wherein the volume ratio of the diamino-substituted tetrachlorodisilane intermediate of the step 2) to tetrahydrofuran is 1: 1-10: 1.
7. Use of the product of the preparation process according to any one of claims 1 to 6, characterized in that liquid bisamino-substituted disilanes with a purity of > 7N are used as precursors for atomic layer deposition of thin films.
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