JP7062069B2 - 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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- JP7062069B2 JP7062069B2 JP2020538039A JP2020538039A JP7062069B2 JP 7062069 B2 JP7062069 B2 JP 7062069B2 JP 2020538039 A JP2020538039 A JP 2020538039A JP 2020538039 A JP2020538039 A JP 2020538039A JP 7062069 B2 JP7062069 B2 JP 7062069B2
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- aminoiodosilane
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- 238000000034 method Methods 0.000 title claims description 24
- 230000002194 synthesizing effect Effects 0.000 title claims description 5
- -1 Amino iodine silane Chemical compound 0.000 title description 10
- KUEHVWCAFFIBQN-UHFFFAOYSA-N N[SiH2]I Chemical compound N[SiH2]I KUEHVWCAFFIBQN-UHFFFAOYSA-N 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 14
- IDIOJRGTRFRIJL-UHFFFAOYSA-N iodosilane Chemical compound I[SiH3] IDIOJRGTRFRIJL-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000012258 stirred mixture Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- VDPDDSHOESGDGI-UHFFFAOYSA-N 2-methyl-N-triiodosilylpropan-2-amine Chemical group C(C)(C)(C)N[Si](I)(I)I VDPDDSHOESGDGI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- CFTHARXEQHJSEH-UHFFFAOYSA-N silicon tetraiodide Chemical compound I[Si](I)(I)I CFTHARXEQHJSEH-UHFFFAOYSA-N 0.000 claims description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- PWTZEFRVBXARTF-UHFFFAOYSA-N N-[(tert-butylamino)-diiodosilyl]-2-methylpropan-2-amine Chemical group C(C)(C)(C)N[Si](I)(I)NC(C)(C)C PWTZEFRVBXARTF-UHFFFAOYSA-N 0.000 claims 1
- CSNURGQHYQKULM-UHFFFAOYSA-N N-[diiodo-(propan-2-ylamino)silyl]propan-2-amine Chemical compound C(C)(C)N[Si](I)(I)NC(C)C CSNURGQHYQKULM-UHFFFAOYSA-N 0.000 claims 1
- CNAQYUMASMYLGO-UHFFFAOYSA-N N-triiodosilylethanamine Chemical compound C(C)N[Si](I)(I)I CNAQYUMASMYLGO-UHFFFAOYSA-N 0.000 claims 1
- HYRHDSZEZYBXBA-UHFFFAOYSA-N N-triiodosilylmethanamine Chemical group CN[Si](I)(I)I HYRHDSZEZYBXBA-UHFFFAOYSA-N 0.000 claims 1
- KIXPPWMNPAQCCP-UHFFFAOYSA-N N-triiodosilylpropan-2-amine Chemical group C(C)(C)N[Si](I)(I)I KIXPPWMNPAQCCP-UHFFFAOYSA-N 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 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
- 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 4
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 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
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000000576 coating method Methods 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
- 239000012528 membrane Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([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
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010189 synthetic method Methods 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
- 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
- 150000001875 compounds Chemical class 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
- 229910052757 nitrogen Inorganic materials 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
- 229910000077 silane Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000126 substance Substances 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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 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
- 238000007098 aminolysis reaction Methods 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
- 238000001816 cooling Methods 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
- 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
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 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
- 238000005192 partition Methods 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
- 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
- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon 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 (10)
- アミノヨードシランの合成法であって、
式SiI4を有するヨードシランを、式NH2R1を有するモノ置換されたアミンと接触させて、式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]
を有するアミノヨードシラン反応生成物を製造することを含む、アミノヨードシランの合成法。 - ヨードシランの、モノ置換されたアミンに対するモル比が、およそ1:2から1:4の範囲にある、請求項1に記載の方法。
- アミノヨードシラン反応生成物及びアルキルアンモニウムヨージド塩が製造される、請求項1に記載の方法。
- 反応が溶媒中で行われる、請求項1に記載の方法。
- 溶媒がトルエンである、請求項4に記載の方法。
- モノ置換されたアミンがt-ブチルアミンであり、アミノヨードシランがt-ブチルアミノトリヨードシランである、請求項1に記載の方法。
- モノ置換されたアミンが、メチルアミン又はエチルアミンであり、アミノヨードシランが、メチルアミノトリヨードシラン又はエチルアミノトリヨードシランである、請求項1に記載の方法。
- モノ置換されたアミンがイソプロピルアミンであり、アミノヨードシランがイソプロピルアミノトリヨードシランである、請求項1に記載の方法。
- アミノヨードシランが、ビス(t-ブチルアミノ)ジヨードシラン、又はビス(イソプロピルアミノ)ジヨードシランである、請求項1に記載の方法。
- 以下の工程:
テトラヨードシランを、反応器に添加する工程;
式NH 2 R1
[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る]
を有するモノ置換されたアミンを反応器に添加して、混合物を生成させる工程;
前記混合物を攪拌して、攪拌された混合物を形成する工程;及び
アミノヨードシランを、攪拌された混合物から単離する工程
を含む、アミノヨードシランの合成法。
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US201862616568P | 2018-01-12 | 2018-01-12 | |
US62/616,568 | 2018-01-12 | ||
PCT/US2019/013165 WO2019140168A1 (en) | 2018-01-12 | 2019-01-11 | Aminoiodosilanes and methods of synthesizing these aminoiodosilanes |
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US (2) | US10640523B2 (ja) |
JP (2) | JP7062069B2 (ja) |
KR (2) | KR102445803B1 (ja) |
CN (1) | CN111630057A (ja) |
TW (1) | TWI711625B (ja) |
WO (1) | WO2019140168A1 (ja) |
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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 |
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 |
CN102471885A (zh) | 2010-04-01 | 2012-05-23 | 乔治洛德方法研究和开发液化空气有限公司 | 使用氨基金属与卤化金属前体组合的含金属氮化物的薄膜沉积 |
US20120277457A1 (en) * | 2010-10-12 | 2012-11-01 | Air Products And Chemicals, Inc. | Aminosilanes and methods for making same |
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KR102445803B1 (ko) | 2022-09-22 |
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US20200231616A1 (en) | 2020-07-23 |
CN111630057A (zh) | 2020-09-04 |
US11312739B2 (en) | 2022-04-26 |
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