JP7399211B2 - アミノヨードシラン、及び当該アミノヨードシランの合成方法 - Google Patents
アミノヨードシラン、及び当該アミノヨードシランの合成方法 Download PDFInfo
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- JP7399211B2 JP7399211B2 JP2022068798A JP2022068798A JP7399211B2 JP 7399211 B2 JP7399211 B2 JP 7399211B2 JP 2022068798 A JP2022068798 A JP 2022068798A JP 2022068798 A JP2022068798 A JP 2022068798A JP 7399211 B2 JP7399211 B2 JP 7399211B2
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- aminoiodosilane
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- butyl
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- KUEHVWCAFFIBQN-UHFFFAOYSA-N N[SiH2]I Chemical compound N[SiH2]I KUEHVWCAFFIBQN-UHFFFAOYSA-N 0.000 title claims description 27
- 238000000034 method Methods 0.000 title description 13
- 230000002194 synthesizing effect Effects 0.000 title description 2
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000007795 chemical reaction product Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- IDIOJRGTRFRIJL-UHFFFAOYSA-N iodosilane Chemical compound I[SiH3] IDIOJRGTRFRIJL-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- DWYFVNQPXDIINF-UHFFFAOYSA-N C(C)(C)(C)N[SiH](I)I Chemical compound C(C)(C)(C)N[SiH](I)I DWYFVNQPXDIINF-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- VDPDDSHOESGDGI-UHFFFAOYSA-N 2-methyl-N-triiodosilylpropan-2-amine Chemical compound C(C)(C)(C)N[Si](I)(I)I VDPDDSHOESGDGI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- CFTHARXEQHJSEH-UHFFFAOYSA-N silicon tetraiodide Chemical compound I[Si](I)(I)I CFTHARXEQHJSEH-UHFFFAOYSA-N 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- -1 ammonium halide salts Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000526 short-path distillation Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 241001120493 Arene Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910004480 SiI4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- OTQBLXPDYHKNHK-UHFFFAOYSA-N [Si]NI Chemical compound [Si]NI OTQBLXPDYHKNHK-UHFFFAOYSA-N 0.000 description 1
- 239000011825 aerospace material Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- AIHCVGFMFDEUMO-UHFFFAOYSA-N diiodosilane Chemical compound I[SiH2]I AIHCVGFMFDEUMO-UHFFFAOYSA-N 0.000 description 1
- RNRZLEZABHZRSX-UHFFFAOYSA-N diiodosilicon Chemical compound I[Si]I RNRZLEZABHZRSX-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 101150009274 nhr-1 gene Proteins 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/10—Vacuum distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本願は、35 USC 119のもとで2018年1月12日に出願された米国特許仮出願第62/616,568号の利益を主張するものであり、その開示内容は、あらゆる目的についてその全体が参照により本願に組み込まれるものとする。
SiI4+z(NH2R1)=SiIy(NHR1)z
式中、R1は、C1~C10アルキル若しくはシクロアルキル、アリール、又はヘテロ基から選択され、y=1~3であり、z=4-yである。
以下の実施例は、非限定的な実施例であり、本発明の実施態様をさらに説明するためのものである。しかしながらこれらの実施例は、すべて網羅することを意図しているわけではなく、また本開示に記載された発明の範囲を制限することを意図しているわけでもない。
Claims (6)
- 式SiIy(NHR1)z
[式中、R1は、シクロアルキル又はアリールから選択され、y=1~3であり、z=4-yである]
を有するアミノヨードシラン。 - yが2であり、zが2である、請求項1に記載のアミノヨードシラン。
- yが1であり、zが3である、請求項1に記載のアミノヨードシラン。
- R 1 が、アリールである、請求項1に記載のアミノヨードシラン。
- R1が、シクロアルキルである、請求項1に記載のアミノヨードシラン。
- アミノヨードシランが、96%超の純度である、請求項1に記載のアミノヨードシラン。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862616568P | 2018-01-12 | 2018-01-12 | |
US62/616,568 | 2018-01-12 | ||
JP2020538039A JP7062069B2 (ja) | 2018-01-12 | 2019-01-11 | アミノヨードシラン、及び当該アミノヨードシランの合成方法 |
PCT/US2019/013165 WO2019140168A1 (en) | 2018-01-12 | 2019-01-11 | Aminoiodosilanes and methods of synthesizing these aminoiodosilanes |
Related Parent Applications (1)
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JP2020538039A Division JP7062069B2 (ja) | 2018-01-12 | 2019-01-11 | アミノヨードシラン、及び当該アミノヨードシランの合成方法 |
Publications (2)
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JP2022105050A JP2022105050A (ja) | 2022-07-12 |
JP7399211B2 true JP7399211B2 (ja) | 2023-12-15 |
Family
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JP2022068798A Active JP7399211B2 (ja) | 2018-01-12 | 2022-04-19 | アミノヨードシラン、及び当該アミノヨードシランの合成方法 |
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Country Status (6)
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US (2) | US10640523B2 (ja) |
JP (2) | JP7062069B2 (ja) |
KR (1) | KR102445803B1 (ja) |
CN (1) | CN111630057A (ja) |
TW (1) | TWI711625B (ja) |
WO (1) | WO2019140168A1 (ja) |
Families Citing this family (3)
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JP7065805B2 (ja) * | 2019-05-13 | 2022-05-12 | 大陽日酸株式会社 | ハロゲン化アミノシラン化合物、薄膜形成用組成物およびシリコン含有薄膜 |
US10988490B1 (en) | 2019-10-03 | 2021-04-27 | Entegris, Inc. | Triiodosilylamine precursor compounds |
CN112430245B (zh) * | 2020-11-24 | 2023-03-03 | 江西晨光新材料股份有限公司 | 一种硅氮杂环氨基硅烷的合成系统及合成方法 |
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WO2017007986A1 (en) | 2015-07-09 | 2017-01-12 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Alkylamino-substituted halocarbosilane precursors |
JP2017507908A (ja) | 2014-01-08 | 2017-03-23 | ディーエヌエフ カンパニー リミテッドDNF Co. Ltd. | 新規なシクロジシラザン誘導体およびその製造方法、並びにそれを用いたシリコン含有薄膜 |
JP2017520532A (ja) | 2014-05-30 | 2017-07-27 | ダウ コーニング コーポレーションDow Corning Corporation | ジイソプロピルアミノ−ジシランの合成方法 |
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US2807635A (en) * | 1952-05-09 | 1957-09-24 | Shell Dev | Silicon amines |
US20060084283A1 (en) | 2004-10-20 | 2006-04-20 | Paranjpe Ajit P | Low temperature sin deposition methods |
TWI498447B (zh) | 2010-04-01 | 2015-09-01 | Air Liquide | 使用胺基金屬與鹵化金屬前驅物組合之含金屬氮化物之薄膜沈積 |
US20120277457A1 (en) * | 2010-10-12 | 2012-11-01 | Air Products And Chemicals, Inc. | Aminosilanes and methods for making same |
US8993072B2 (en) | 2011-09-27 | 2015-03-31 | Air Products And Chemicals, Inc. | Halogenated organoaminosilane precursors and methods for depositing films comprising same |
US20140273531A1 (en) | 2013-03-14 | 2014-09-18 | Asm Ip Holding B.V. | Si PRECURSORS FOR DEPOSITION OF SiN AT LOW TEMPERATURES |
US9777373B2 (en) | 2015-12-30 | 2017-10-03 | American Air Liquide, Inc. | Amino(iodo)silane precursors for ALD/CVD silicon-containing film applications and methods of using the same |
US9701695B1 (en) * | 2015-12-30 | 2017-07-11 | American Air Liquide, Inc. | Synthesis methods for amino(halo)silanes |
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2019
- 2019-01-08 US US16/242,706 patent/US10640523B2/en active Active
- 2019-01-11 TW TW108101201A patent/TWI711625B/zh active
- 2019-01-11 WO PCT/US2019/013165 patent/WO2019140168A1/en active Application Filing
- 2019-01-11 KR KR1020207019708A patent/KR102445803B1/ko active IP Right Grant
- 2019-01-11 JP JP2020538039A patent/JP7062069B2/ja active Active
- 2019-01-11 CN CN201980007669.4A patent/CN111630057A/zh active Pending
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2020
- 2020-04-02 US US16/838,694 patent/US11312739B2/en active Active
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2022
- 2022-04-19 JP JP2022068798A patent/JP7399211B2/ja active Active
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JP2007051363A (ja) | 2005-05-16 | 2007-03-01 | Air Products & Chemicals Inc | Cvd炭窒化ケイ素膜用前駆体 |
US20140273477A1 (en) | 2013-03-14 | 2014-09-18 | Asm Ip Holding B.V. | Si PRECURSORS FOR DEPOSITION OF SiN AT LOW TEMPERATURES |
JP2017507908A (ja) | 2014-01-08 | 2017-03-23 | ディーエヌエフ カンパニー リミテッドDNF Co. Ltd. | 新規なシクロジシラザン誘導体およびその製造方法、並びにそれを用いたシリコン含有薄膜 |
JP2017520532A (ja) | 2014-05-30 | 2017-07-27 | ダウ コーニング コーポレーションDow Corning Corporation | ジイソプロピルアミノ−ジシランの合成方法 |
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Also Published As
Publication number | Publication date |
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TW201932474A (zh) | 2019-08-16 |
CN111630057A (zh) | 2020-09-04 |
JP2021510691A (ja) | 2021-04-30 |
US10640523B2 (en) | 2020-05-05 |
US20190218238A1 (en) | 2019-07-18 |
US20200231616A1 (en) | 2020-07-23 |
WO2019140168A1 (en) | 2019-07-18 |
JP2022105050A (ja) | 2022-07-12 |
TWI711625B (zh) | 2020-12-01 |
JP7062069B2 (ja) | 2022-05-02 |
KR20200087869A (ko) | 2020-07-21 |
US11312739B2 (en) | 2022-04-26 |
KR20220132660A (ko) | 2022-09-30 |
KR102445803B1 (ko) | 2022-09-22 |
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