CN113710677A - 氧族硅环戊烷 - Google Patents
氧族硅环戊烷 Download PDFInfo
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title abstract description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 title abstract description 4
- HZBAVWLZSLOCFR-UHFFFAOYSA-N oxosilane Chemical compound [SiH2]=O HZBAVWLZSLOCFR-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000000758 substrate Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001033 ether group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 229910052710 silicon Inorganic materials 0.000 abstract description 7
- 238000007142 ring opening reaction Methods 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- -1 oxosilane cyclopentane compound Chemical class 0.000 abstract description 4
- 239000010703 silicon Substances 0.000 abstract description 4
- 229910052714 tellurium Inorganic materials 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 238000000427 thin-film deposition Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 238000000231 atomic layer deposition Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 238000000151 deposition Methods 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910000661 Mercury cadmium telluride Inorganic materials 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 229910008048 Si-S Inorganic materials 0.000 description 2
- 229910006336 Si—S Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- RMILLRSLWHOHQS-UHFFFAOYSA-N chloro-(3-chloro-2-methylpropyl)-dimethylsilane Chemical compound ClCC(C)C[Si](C)(C)Cl RMILLRSLWHOHQS-UHFFFAOYSA-N 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 229910000618 GeSbTe Inorganic materials 0.000 description 1
- 229910007991 Si-N Inorganic materials 0.000 description 1
- 229910006294 Si—N Inorganic materials 0.000 description 1
- 229910006348 Si—Se Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- MCMSPRNYOJJPIZ-UHFFFAOYSA-N cadmium;mercury;tellurium Chemical compound [Cd]=[Te]=[Hg] MCMSPRNYOJJPIZ-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 150000001787 chalcogens Chemical class 0.000 description 1
- JTDLZUISELNNAS-UHFFFAOYSA-N chloro-(chloromethyl)-methyl-(2-methylpropyl)silane Chemical compound ClC[Si](Cl)(C)CC(C)C JTDLZUISELNNAS-UHFFFAOYSA-N 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000010505 homolytic fission reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003958 selenols Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical compound [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 description 1
- 238000007736 thin film deposition technique Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
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- 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
- C07F7/0896—Compounds with a Si-H linkage
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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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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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
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
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- 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
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Abstract
描述了一种新的化合物,称为氧族硅环戊烷。这些化合物是含有硅‑硒键或硅‑碲键的五元环结构,如式(I)和(II)所示。在这些化合物中,硅和环碳上的取代基可以是氢、烷基、烷氧基、芳香族或醚基。氧族硅环戊烷化合物与羟基和其他质子官能团发生开环反应,可用于制备适用于ALD和CVD等薄膜沉积技术的基底。
Description
相关申请的交叉引用
本申请要求对2019年4月2日提交的供待审的美国临时专利申请号为62/827,970的优先权,其公开内容通过引用整体并入本文。
背景技术
在薄膜技术中,通常表面经修饰后呈现特定的化学官能团或修饰基底行为以实现沉积技术。后者在需要超薄保形层的技术中尤其重要。例如,在用于光伏应用的硒化镉和碲化镉薄膜组合物、用于传感器应用的汞-碲化镉(HgCdTe)沉积以及用于相变存储器和电容器应用的锗-锑-碲(GST)沉积中,原子层沉积(ALD)技术变得越来越重要。在这些薄膜沉积方案中观察到的一个普遍的问题是在ALD初始阶段每个周期的生长缓慢,有时也称为ALD过程中的孵化或诱导。通常,这种缓慢的生长与基底的反应性有关,基底的成分与待沉积薄膜的成分不同。本领域仍然需要能够有效地启动沉积过程的基底。
发明内容
描述了一种具有式(I)或(II)结构的氧族硅环戊烷,其中,Ra、Rb、Rc、Rd、Re、Rf、R和R'各自独立地选自氢、具有1-约8个碳原子的烷基、具有1-约8个碳原子的烷氧基、芳基和醚基;
具体实施方式
本发明涉及一系列新的杂环硅烷,称为氧族硅环戊烷。术语“氧族(chalcogen)”是指周期表第16族中的元素,本发明所包含的氧族包括硒(Se)和碲(Te)。因此,本发明更具体地涉及硒硅环戊烷和碲硅环戊烷。这些化合物与羟基和其他质子官能团发生理想的开环反应。此外,用这些材料进行表面改性,可使基底适用于薄膜沉积技术,如ALD(原子层沉积)和CVD(化学气相沉积)。
本发明的硒硅环戊烷和碲硅环戊烷是含有硅-硒键或硅-碲键的5元环结构,如下列具有式(I)和(II)结构的化合物所示;
本发明的氧族硅环戊烷上最简单的成员在环上或硅上没有取代,即所有的Ra至Rf,R和R′取代基都是氢原子,如下面具有式(III)和(IV)的结构的化合物所示:
更一般地说,环碳的取代基Ra至Rf,硅原子上的取代基R和R'各自独立地为氢或选自下组的有机基团:具有1-约8个碳原子的烷基和烷氧基,更优选地,4个或更少碳原子的烷基和烷氧基、芳香基团和醚基。更优选地,所述取代基为氢、烷基或烷氧基,更优选氢、甲基、甲氧基或乙氧基。例如,氧族硅环戊烷上的硅原子和环碳上的一个原子被甲基取代,2,2,4-三甲基-1-硒-2-硅环戊烷和2,2,4-三甲基-1-碲-2-硅环戊烷,如下式(V)和式(VI)所示。
根据本发明的其他可能的化合物的实例包括但不限于具有以下结构的化合物:
本发明的氧族硅环戊烷可通过3-氯异丁基二甲基氯硅烷与氧族锂反应制备,如方案I所示:
本发明化合物也可通过3-氯异丁基三烷氧基硅烷与氧族锂反应制备,如方案II所示:
可以进行类似的反应以产生本发明的替代化合物,该替代化合物在硅环戊烷环的第四位不含甲基取代基。本领域技术人员能很好的理解这种反应。烷氧基取代的化合物可用氢化铝锂或二异丁基氢化铝还原,以产生在硅上具有氢取代基的本发明化合物。
本发明的材料与例如含有羟基、硫醇和胺基的质子基底进行开环反应,在相对于基底的远端位置产生C-Se-H(硒醇)或C-Te-H(碲醇)的元素。一般的和特定(例如碲)的开环反应如方案III和方案IV所示。
正如Harmgarth等人所述(无机与普通化学杂志(Zeitschrift für Anorganischeund Allgemeine Chemie),2017,1150-1166),对于GST薄膜,一旦碲原子可用作沉积起始层的一部分,可使用各种前体清洁地生长薄膜。因此,由本发明材料制备的基底对于生长清洁薄膜是有效的。
氧族硅环戊烷和硅环戊烷之间的另一个有趣的比较是氢核磁谱中Si-Me峰的相对位移。硫系Si-S中最典型的位移与Si-CH部分相关。然而,杂原子尺寸的增大和电负性的减小导致甲基峰明显的上场位移。位移的变化表明硅原子上的部分正电荷更强,从而增加了硅的路易斯酸度,使硅-杂原子键更容易异裂,从而对亲核试剂和质子基底更具反应性。另外,对硅杂原子键的一般键离解能的比较表明,Si-Se和Si-Te的离解能相似,而Si-N的离解能较弱,Si-S的离解能较强。虽然这些值仅代表均裂解离,但它们能很好的指示键强度,与羟基和其他基团进行开环反应的热力学驱动力是有利的。
现在将结合以下非限制性实施例来阐述本发明。
实施例 1:2,2,4-三甲基-1-硒-2-硅环戊烷的合成
向500mLTHF中新切割的锂金属(13.8g,1.9mol)加入额外300mL THF中的催化量的二苯乙炔(8.8g,0.05mol)溶液。该加入是略微放热的,并形成红褐色溶液。在放热停止后(约90分钟),通过粉末添加漏斗少量地添加硒(75g,0.9mol),导致大放热。所得混合物在回流下加热8小时以确保最大程度消耗锂。制备含有175.88g(0.9mol)3-氯异丁基二甲基氯硅烷(Gelest市售获得)和1.35g(0.01mol)BF3·Et2O的溶液并滴加到Li2Se中,导致放热。反应回流8小时。在高真空下从反应中除去所有挥发物,所得混合物在新鲜装置中分步蒸馏(维格罗分馏柱),得到2,2,4-三甲基-1-硒-2-硅环戊烷(沸点:63-4℃/10mm;密度:1.195g/mL)。
分离得到目标化合物为黄橙色液体,收率28.7%。GC-MS和NMR结果与结构一致。1HNMR(CDCl3,400MHz):δ0.45(s,3H),0.51(s,3H),0.65(dd,1H,J=11.6,14.0Hz),1.13(d,3H,J=6.4Hz),1.22(ddd,1H,J=1.6,4.8,14.0Hz),2.18(m,1H),2.52(t,1H,J=10Hz),2.89(ddd,1H,J=2.0,4.8,10.0Hz).
实施例2:2,2,4-三甲基-1-碲-2-硅环戊烷的合成
向200mLTHF中新切割的锂金属(10.9g,1.6mol)加入额外200mL的THF中催化量的二苯乙炔(7.3g,0.04mol)溶液。该加入是略微放热的,并形成红褐色溶液。在放热停止后(约90分钟),通过粉末添加漏斗少量地添加碲粉末(100g,0.8mol),导致大放热。所得混合物在回流下加热8小时以确保最大程度消耗锂。制备含有145.1g(0.8mol)氯异丁基二甲基氯硅烷(Gelest市售获得)和1.1g(0.01mol)BF3·Et2O的溶液并滴加到Li2Te中,导致放热。反应回流8小时。在高真空下从反应中除去所有挥发物,所得混合物在新鲜装置中分步蒸馏(维格罗分馏柱),得到2,2,4-三甲基-1-碲-2-硅环戊烷(沸点61-3℃/4)。分离得到目标化合物为无色液体,收率30.3%。一旦暴露在光下,即开始呈现橙色。GCMS和NMR验证了结构。1H NMR(CDCl3,400MHz):δ0.61(s,3H),0.67(s,3H),0.72(dd,1H,J=10.8,14.0Hz),1.14(d,3H,J=6.4Hz),1.34(ddd.1H,J=1.6,3.6,13.6Hz),2.12(m,1H),2.62(t,1H,J=10Hz),2.91(ddd,1H,J=1.6,4.4,10.4Hz)。
本领域技术人员将理解,可以在不脱离上述实施例的广泛创造性概念的情况下对其进行更改。此外,基于本公开,本领域普通技术人员将进一步认识到,在不脱离本发明的精神和范围的情况下,可以改变上述组分的相对比例。因此,应当理解,本发明不限于所公开的特定实施例,而是旨在覆盖由所附权利要求所定义的本发明的精神和范围内的修改。
Claims (10)
2.如权利要求1所述的氧族硅环戊烷,其特征在于,Ra、Rb、Rc、Rd、Re、Rf、R和R'各自独立地选自氢、具有1-约8个碳原子的烷基和具有1-约8个碳原子的烷氧基。
8.如权利要求1所述的氧族硅环戊烷与质子物质的反应产物。
9.如权利要求7所述的反应产物,其特征在于,质子物质是基底。
10.一种在质子基底上形成ALD起始层的方法,其特征在于,所述方法包括将质子基底与如权利要求1所述的氧族硅环戊烷反应。
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