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TWI752929B - 合成二矽烷基胺與聚矽烷基胺 - Google Patents

合成二矽烷基胺與聚矽烷基胺 Download PDF

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TWI752929B
TWI752929B TW105141894A TW105141894A TWI752929B TW I752929 B TWI752929 B TW I752929B TW 105141894 A TW105141894 A TW 105141894A TW 105141894 A TW105141894 A TW 105141894A TW I752929 B TWI752929 B TW I752929B
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孝賓 周
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中國大陸商南大光電半導體材料有限公司
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Abstract

本發明提供了製備矽烷基胺(例如，二矽烷基胺與聚矽烷基胺)之程序以及包含矽烷基胺之組成物。在一實施例中，本發明提供了製備矽烷基胺化合物之程序，該程序包含將通式RR1N-(SixH2x+1)之起始化合物與通式R2R3NH之胺化合物反應，以產生通式R2 mR3 n-N(SixH2x+1)3-m-n之矽烷基胺化合物。

Description

合成二矽烷基胺與聚矽烷基胺
本發明提供了製備矽烷基胺(例如，二矽烷基胺與聚矽烷基胺)之程序。本發明還提供了包含矽烷基胺之組成物。
通常在沉積應用中使用前驅物化合物與材料。沉積應用包括化學或物理氣相沉積。可籍由化學氣相沉積對前驅物化合物進行沉積，以在多種類型之基材上形成薄膜，例如矽晶圓和其他電子組件。影響薄膜之性能的因素有多種，包括基材之性質、沉積之方法與條件、以及前驅物化合物之性質。
沉積應用中存在缺陷。例如，某些前驅物在處理和使用過程中會導致問題。使用某些前驅物時，產生副產物之副反應可能會使產生的薄膜含有某些雜質。副產物可能包括危險組分，例如氫和氯化合物。
二矽烷基胺可用於沉積含矽之薄膜。該等薄膜包括具有非晶矽、結晶矽、氮化矽、氧化矽、碳參雜氧化矽、矽碳-氮化物、以及氧氮化矽之薄膜。二矽烷基胺係用於沉積含矽薄膜之有前景的化學氣相沉積(CVD)和原子層沉積(ALD)前驅物。例如，二矽烷基胺可用 於在各種基材上沉積Si、SiO、SiO2、SiON、或SiN薄膜，例如3D NAND裝置。
目前僅可製作有限數量的二矽烷基胺，因此需要更具商業利益和技術實用性之方法製作各種二矽烷基胺和聚矽烷基胺材料。對新穎二矽烷基胺和聚矽烷基胺之需求可產生更優良之應用效能和更優良之薄膜性能。
本發明提供了製備矽烷基胺(例如，二矽烷基胺與聚矽烷基胺)之程序。本發明還提供了包含矽烷基胺之組成物。
在一實施例中，本發明提供了製備矽烷基胺化合物之程序，該程序將包含通式RR1N-(SixH2x+1) (I)之起始化合物與通式R2R3NH (II)之胺化合物反應，以產生通式R2 mR3 n-N(SixH2x+1)3-m-n (III)之矽烷基胺化合物，其中R和R1獨立地係氫、具有6至10個碳原子之經取代或未經取代之芳基、具有1至10個碳原子之經取代或未經取代之烷基、或具有5至10個碳原子之經取代或未經取代之環烷基；R2和R3獨立地係氫、具有6至10個碳原子之經取代或未經取代之芳基、具有1至10個碳原子之經取代或未經取代之烷基、具有5至 10個碳原子之經取代或未經取代之環烷基、或通式-SixH2x+1之矽烷；x係自2至10的整數；及m或n獨立地係0、1、或2，且m+n係2或更小。
在另一實施例中，本發明提供了通式R2 mR3 n-N(SixH2x+1)3-m-n (III)之矽烷基胺化合物，其中R2和R3獨立地係氫、具有6至10個碳原子之經取代或未經取代之芳基、具有1至10個碳原子之經取代或未經取代之烷基、具有5至10個碳原子之經取代或未經取代之環烷基；x係2至10；及m或n獨立地係0、1、或2，且m+n係2或更小。
該發明關於一種從胺基轉移作用開發而來的新穎合成方法以及使用該方法製備例示性矽烷基胺。在一實施例中，本發明提供了製備矽烷基胺化合物之程序，該程序包含將通式RR1N-(SixH2x+1) (I)之起始化合物與通式R2R3NH (II)之胺化合物反應，以產生通式R2 mR3 n-N(SixH2x+1)3-m-n (III)之矽烷基胺化合物，其中R和R1獨立地係氫、具有6至10個碳原子之經取代或未經取代之芳基、具有1至10個碳原子之經取代或未經取代之烷基、或具有5 至10個碳原子之經取代或未經取代之環烷基；R2和R3獨立地係氫、具有6至10個碳原子之經取代或未經取代之芳基、具有1至10個碳原子之經取代或未經取代之烷基、具有5至10個碳原子之經取代或未經取代之環烷基、或通式-SixH2x+1之矽烷；x係自2至10的整數；且m或n獨立地係0、1、或2，且m+n係2或更小。
在該發明中，證明胺基轉移作用係一種製備表1中二矽烷基胺之5種結構(結構IV除外)的通用方法。二異丙基二矽烷基胺(DPDS)與二級胺透過方程式1之胺基轉移作用形成結構-I二矽烷基胺，與一級胺透過方程式2形成結構-II或結構-III二矽烷基胺，或與氨透過方程式3形成結構-V或VI二矽烷基胺。表2顯示了室溫條件下30分鐘後，與各種胺基轉移劑之胺基轉移作用所獲得的GC轉換率%。在某些情況中，低GC轉換率%透過方法優化而提高(在本文中未報告資料，但可以提供)。胺基轉移產物之特徵係含有GC-MS和1H NMR。大多數產物之組成物係新品種。已使用標準純化方法(例如，蒸餾)對幾種新品種進行分離，並將其純化至電子等級。
二矽烷基胺之結構
二矽烷基胺係一族分子，其具有通式結構NRmR’n(SiH2SiH3)3-m-n，其中R和R’可係氫或任何烴基；m、n係0、1或2。該系列分子包括單(二矽烷基)胺、雙(二矽烷基)胺、及參(二矽烷基)胺，此類胺由表1中的6種結構表示。
Figure 105141894-A0305-02-0007-1
Figure 105141894-A0305-02-0007-2
Figure 105141894-A0305-02-0007-3
Figure 105141894-A0305-02-0008-4
Figure 105141894-A0305-02-0008-5
雖然透過DPDS證明了胺基轉移作用之方法，但應將該方法擴展應用到其他胺基官能氫化更高級之矽烷起始材料，以製作出已有材料或新材料。例如，式SixHy(NRR’)z之材料，其中R和R’係 H或氫或烴基，x至少係2，且y和z係變量，可與氨、一級胺或二級胺進行胺基轉移作用，形成一系列已有材料或新材料。
實例
實例1.合成二矽烷基二乙胺
於Schlenk管子內裝入0.65g(8.92mmol)二乙胺。然後在室溫下，於1分鐘之內逐滴滴入0.72g(4.46mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可以38.8%之轉換率生成二矽烷基二乙胺。GC-MS確認了二矽烷基二乙胺之組成物。
實例2.合成二矽烷基甲胺與雙(二矽烷基)甲胺
於Schlenk管子內裝入3.10ml 2.0M(6.20mmol)甲胺溶液(於THF中)。然後在室溫下，於1分鐘之內逐滴滴入0.50g(3.10mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以69.4%和22.0%之轉換率生成二矽烷基甲胺和雙(二矽烷基)甲胺。GC-MS確認了二矽烷基甲胺與雙(二矽烷基)甲胺之組成物。
實例3.合成二矽烷基乙胺與雙(二矽烷基)乙胺
於Schlenk管子內裝入2.60ml 2.0M(5.20mmol)乙胺溶液(於THF中)。然後在室溫下，於1分鐘之內逐滴滴入0.42g (2.60mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以73.7%和23.8%之轉換率生成二矽烷基乙胺與雙(二矽烷基)乙胺。GC-MS確認了二矽烷基甲胺與雙(二矽烷基)甲胺之組成物。
實例4.合成二矽烷基丙胺與雙(二矽烷基)丙胺
於Schlenk管子內裝入0.62g(10.4mmol)丙胺。然後在室溫下，於1分鐘之內逐滴滴入0.84g(5.20mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以62.5%和21.0%之轉換率生成二矽烷基丙胺與雙(二矽烷基)丙胺。GC-MS確認了二矽烷基丙胺與(二矽烷基)丙胺之組成物。
實例5.合成二矽烷基丁胺與雙(二矽烷基)丁胺
於Schlenk管子內裝入0.77g(10.5mmol)丁胺。然後在室溫下，於1分鐘之內逐滴滴入0.85g(5.27mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以71.3%和25.0%之轉換率生成二矽烷基丁胺與雙(二矽烷基)丁胺。GC-MS確認了二矽烷基丁胺與雙(二矽烷基)丁胺之組成物。
實例6.合成二矽烷基(二級丁基)胺與雙(二矽烷基)(二級丁基)胺
於Schlenk管子內裝入0.80g(10.9mmol)2-胺基丁烷。然後在室溫下，於1分鐘之內逐滴滴入0.88g(5.45mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以96.9%和1.0%之轉換率生成二矽烷基(二級丁基)胺與雙(二矽烷基)(二級丁基)胺。GC-MS確認了二矽烷基(二級丁基)胺與雙(二矽烷基)(二級丁基)胺之組成物。
實例7.合成二矽烷基戊胺與雙(二矽烷基)戊胺
於Schlenk管子內裝入0.86g(9.91mmol)戊胺。然後在室溫下，於1分鐘之內逐滴滴入0.80g(4.96mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以51.2%和13.2%之轉換率生成二矽烷基戊胺與雙(二矽烷基)戊胺。GC-MS確認了二矽烷基戊胺與雙(二矽烷基)戊胺之組成物。
實例8.合成二矽烷基(1-甲基丁基)胺與雙(二矽烷基)(1-甲基丁基)胺
於Schlenk管子內裝入0.96g(11.0mmol)2-胺基戊烷。然後在室溫下，於1分鐘之內逐滴滴入0.89g(5.51mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以95.2%和0.8%之轉換率生成二矽烷基(1-甲基丁基)胺與雙(二矽烷基)(1-甲基丁基)胺。GC-MS確認了二矽烷基(1-甲基丁基)胺與雙(二矽烷基)(1-甲基丁基)胺 之組成物。
實例9.合成二矽烷基(1-乙基丙基)胺
於Schlenk管子內裝入0.78g(4.83mmol)二異丙基二矽烷基胺。然後在室溫下，於1分鐘之內逐滴滴入0.84g(9.67mmol)3-胺基戊烷。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可以97.7%之轉換率生成二矽烷基(1-乙基丙基)胺。GC-MS確認了二矽烷基(1-乙基丙基)胺之組成物。
實例10.合成二矽烷基(1,2-二甲基丙基)胺
於Schlenk管子內裝入0.93g(10.7mmol)1,2-二甲基丙基胺。然後在室溫下，於1分鐘之內逐滴滴入0.86g(5.33mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可以98.0%之轉換率生成二矽烷基(1,2-二甲基丙基)胺。GC-MS確認了二矽烷基(1,2-二甲基丙基)胺之組成物。
實例11.合成二矽烷基(三級戊基)胺
於Schlenk管子內裝入0.76g(4.71mmol)二異丙基二矽烷基胺。然後在室溫下，於1分鐘之內逐滴滴入0.82g(9.42mmol)三級戊基胺。將其攪動30分鐘後，產物即可用於GC-FID和 GC-MS分析之樣本。基於GC-FID積分，即可以83.2%之轉換率生成二矽烷基(三級戊基)胺。GC-MS確認了二矽烷基(三級戊基)胺之組成物。
實例12.合成二矽烷基(環戊基)胺與雙(二矽烷基)(環戊基)胺
於Schlenk管子內裝入0.89g(5.51mmol)二異丙基二矽烷基胺。然後在室溫下，於1分鐘之內逐滴滴入0.94g(11.0mmol)環戊基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以84.3%和12.3%之轉換率生成二矽烷基(環戊基)胺與雙(二矽烷基)(環戊基胺)胺。GC-MS確認了二矽烷基(環戊基)胺與雙(二矽烷基)(環戊基)胺之組成物。
實例13.合成二矽烷基(環己基)胺與雙(二矽烷基)(環己基)胺
於Schlenk管子內裝入0.77g(4.77mmol)二異丙基二矽烷基胺。然後在室溫下，於1分鐘之內逐滴滴入0.95g(9.54mmol)環己基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可各別以92.2%和5.1%之轉換率生成二矽烷基(環己基)胺與雙(二矽烷基)(環己基)胺。GC-MS確認了二矽烷基(環己基)胺與雙(二矽烷基)(環己基)胺之組成物。
實例14.合成二矽烷基苯胺
於Schlenk管子內裝入0.85g(5.27mmol)二異丙基 二矽烷基胺。然後在室溫下，於30秒之內逐滴滴入0.49g(5.27mmol)苯胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可以74.1%之轉換率生成二矽烷基苯胺。GC-MS確認了二矽烷基苯胺之組成物。
實例15.合成二矽烷基(2-甲基苯基)胺
於Schlenk管子內裝入0.82g(5.08mmol)二異丙基二矽烷基胺。然後在室溫下，於1分鐘之內逐滴滴入0.54g(5.08mmol)鄰-甲苯胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可以38.6%之轉換率生成二矽烷基(2-甲基苯基)胺。GC-MS確認了二矽烷基(2-甲基苯基)胺之組成物。
實例16.合成二矽烷基(2,6-二甲苯基)胺
於Schlenk管子內裝入0.69g(5.70mmol)2,6-二甲基苯胺。然後在室溫下，於1分鐘之內逐滴滴入0.92g(5.70mmol)二異丙基二矽烷基胺。將其攪動30分鐘後，產物即可用於GC-FID和GC-MS分析之樣本。基於GC-FID積分，即可以35.0%之轉換率生成二矽烷基(2,6-二甲苯基)胺。GC-MS確認了二矽烷基(2,6-二甲苯基)胺之組成物。
實例17.合成雙(二矽烷基)胺
於250ml巴氏反應器內裝入66.6g(0.413mol)二異丙基二矽烷基胺。然後在室溫下，於10分鐘之內鼓泡5.28g(0.310mol)氨。將其攪動1小時後，巴氏反應器中之壓力被排空，然後打開巴氏反應器。產物即可用於GC-TCD和GC-MS分析之樣本。基於GC-TCD積分，即可以90%之轉換率生成雙(二矽烷基)胺。GC-MS確認了雙(二矽烷基)胺之組成物。
實例18.透過胺基轉移作用合成參(二矽烷基)胺
於100ml之圓底燒瓶內裝入5.99g實例17中製備之產物。該產物含有2.29g(16.6mmol)雙(二矽烷基)胺。然後在室溫下，快速添加2.31g(14.3mmol)(二矽烷基)(二異丙基)胺。於130℃下加熱反應混合物17個小時，在此期間會持續蒸餾出揮發性物質。產物即可用於GC-TCD和GC-MS分析之樣本。基於GC-TCD積分，即可以71%之轉換率生成參-二矽烷基胺。GC-MS確認了參-二矽烷基胺之組成物。
實例19.透過熱再分配合成參(二矽烷基)胺
於100ml之圓底燒瓶內裝入13.0g(94.5mmol)雙(二矽烷基)胺。於110℃下將燒瓶加熱18個小時。產物即可用於GC-TCD和GC-MS分析之樣本。基於GC-TCD積分，即可以60%之轉換率生成參(二矽烷基)胺。GC-MS確認了參(二矽烷基)胺之組成物。
實例20.透過熱再分配合成參(二矽烷基)胺
於燒瓶內裝入雙(二矽烷基)胺。於110℃下將燒瓶加熱27個小時，將雙(二矽烷基)胺轉換成參(二矽烷基)胺和氨。產物即可用於GC-TCD和GC-MS分析之樣本。基於GC-TCD積分，即生成參(二矽烷基)胺。GC-MS確認了參(二矽烷基)胺之組成物。於10-段管柱內對粗產物進行蒸餾，以回收98%之純參(二矽烷基)胺。
實例21.合成雙二矽烷基胺
於1.5升之高壓巴氏反應器內裝入375g二異丙基二矽烷基胺。在攪動的同時，透過將壓力上升至40psig並下降至20psig，經由浸漬管口於60分鐘內半連續地添加28g無水氨。反應器之起始溫度係20℃，並於添加氨的過程中上升至27℃。伴隨攪動與周期性氮氣吹掃，反應器的溫度在1小時之內冷卻至0°。巴氏反應器中之壓力被排空，然後打開巴氏反應器。產物即可用於GC-TCD和GC-MS分析之樣本。基於GC-TCD積分，粗產物包含38%之雙(二矽烷基)胺和8%之二異丙基二矽烷基胺。GC-MS確認了雙(二矽烷基)胺之組成物。然後使用5-段管柱在150mmHg與60℃下對粗產物進行蒸餾，以回收雙(二矽烷基)胺。

Claims (10)

  1. 一種製備矽烷基胺化合物之程序，該程序包含將通式RR1N-(SixH2x+1) (I)之起始化合物與通式R2R3NH (II)之胺化合物反應，以產生通式R2 mR3 n-N(SixH2x+1)3-m-n (III)之該矽烷基胺化合物，其中R和R1獨立地係氫、具有6至10個碳原子之經取代或未經取代之芳基、具有1至10個碳原子之經取代或未經取代之烷基、或具有5至10個碳原子之經取代或未經取代之環烷基；R2和R3獨立地係式-SixH2x+1之矽烷；x係自2至10的整數；及m及n係0。
  2. 如請求項1之程序，其中該式(I)之起始化合物包含二烷基二矽烷基胺。
  3. 如請求項1之程序，其中該式(I)之起始化合物之R和R1包含具有1至4個碳原子之經取代或未經取代之烷基，且x係自2至4的整數。
  4. 如請求項1或2之程序，其中該式(I)之起始化合物之R和R1包含具有1至3個碳原子之經取代或未經取代之烷基，且x係自2至3的整數。
  5. 如請求項1至3中任一項之程序，其中該式(I)之起始化合物包含二異丙基二矽烷基胺。
  6. 如請求項1之程序，其中該式(II)之胺化合物之R2和R3係式-SixH2x+1之矽烷，其中x係自2至3的整數。
  7. 如請求項1之程序，其中該式(II)之胺係雙-二矽烷基胺。
  8. 如請求項1之程序，其中該式(III)之矽烷基胺化合物包含參(二矽烷基)胺。
  9. 如請求項1至3及6至8中任一項之程序，其中式(II)與式(I)之莫耳比係自0.1：1至100：1。
  10. 一種藉由請求項1之程序製備之通式R2 mR3 n-N(SixH2x+1)3-m-n (III)之矽烷基胺化合物，其中R2和R3獨立地係式-SixH2x+1之矽烷；x係自2至10的整數；及m及n係0。
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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
CN111978346A (zh) 2019-05-23 2020-11-24 中国石油天然气股份有限公司 芳胺基硅烷化合物、丙烯聚合催化剂及其制备与应用
CN116457310A (zh) * 2020-10-23 2023-07-18 恩特格里斯公司 制备碘硅烷的方法
CN115260223B (zh) * 2022-09-26 2022-12-23 江苏南大光电材料股份有限公司 无氯催化剂于制备二异丙胺硅烷中的用途
CN115591259B (zh) * 2022-12-12 2023-04-07 天津绿菱气体有限公司 一种利用副产物再生三甲硅烷基胺的反应装置及方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201500365A (zh) * 2013-06-26 2015-01-01 Air Prod & Chem 氮雜－多矽烷前驅物及包含氮雜－多矽烷前驅物的膜沉積方法

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4675424A (en) * 1986-03-19 1987-06-23 Union Carbide Corporation Method for making polysilazanes
JPH0363284A (ja) 1989-08-01 1991-03-19 Mitsui Petrochem Ind Ltd シラザン類の製造方法
US6391803B1 (en) * 2001-06-20 2002-05-21 Samsung Electronics Co., Ltd. Method of forming silicon containing thin films by atomic layer deposition utilizing trisdimethylaminosilane
US7098150B2 (en) * 2004-03-05 2006-08-29 Air Liquide America L.P. Method for novel deposition of high-k MSiON dielectric films
US20060051975A1 (en) * 2004-09-07 2006-03-09 Ashutosh Misra Novel deposition of SiON dielectric films
US7875312B2 (en) * 2006-05-23 2011-01-25 Air Products And Chemicals, Inc. Process for producing silicon oxide films for organoaminosilane precursors
JP5547418B2 (ja) * 2009-03-19 2014-07-16 株式会社Ａｄｅｋａ 化学気相成長用原料及びこれを用いたシリコン含有薄膜形成方法
US20110136347A1 (en) * 2009-10-21 2011-06-09 Applied Materials, Inc. Point-of-use silylamine generation
JP5623296B2 (ja) 2010-01-15 2014-11-12 信越化学工業株式会社 トリシリルアミンの製造方法
KR20110090711A (ko) 2010-02-04 2011-08-10 녹십자수의약품(주) 신규한 돼지 써코바이러스 타입 2 및 그의 용도
US8912353B2 (en) * 2010-06-02 2014-12-16 Air Products And Chemicals, Inc. Organoaminosilane precursors and methods for depositing films comprising same
US8771807B2 (en) * 2011-05-24 2014-07-08 Air Products And Chemicals, Inc. Organoaminosilane precursors and methods for making and using same
BR112014001066A2 (pt) 2011-07-20 2017-02-21 Allergan Inc toxinas botulínicas para uso em um método para tratamento de depósitos adiposos
KR101970850B1 (ko) * 2011-10-07 2019-04-19 레르 리키드 쏘시에떼 아노님 뿌르 레？드 에렉스뿔라따시옹 데 프로세데 조르즈 클로드 트리실릴아민의 응축상 제조 장치 및 방법
KR101367190B1 (ko) 2011-12-27 2014-02-26 제이에스아이실리콘주식회사 트리스(알콕시실릴)아민의 제조 방법 및 트리실릴아민의 제조 방법
US8871656B2 (en) * 2012-03-05 2014-10-28 Applied Materials, Inc. Flowable films using alternative silicon precursors
US9337018B2 (en) * 2012-06-01 2016-05-10 Air Products And Chemicals, Inc. Methods for depositing films with organoaminodisilane precursors
DE102013207442A1 (de) * 2013-04-24 2014-10-30 Evonik Degussa Gmbh Verfahren und Vorrichtung zur Herstellung von Silanen
US9284198B2 (en) 2013-06-28 2016-03-15 Air Products And Chemicals, Inc. Process for making trisilylamine
US9382269B2 (en) * 2013-09-27 2016-07-05 Voltaix, Llc Halogen free syntheses of aminosilanes by catalytic dehydrogenative coupling
US9233990B2 (en) * 2014-02-28 2016-01-12 Air Products And Chemicals, Inc. Organoaminosilanes and methods for making same
WO2015184201A1 (en) * 2014-05-30 2015-12-03 Dow Corning Corporation Monoaminosilane compounds
US9777025B2 (en) * 2015-03-30 2017-10-03 L'Air Liquide, Société pour l'Etude et l'Exploitation des Procédés Georges Claude Si-containing film forming precursors and methods of using the same
TWI752929B (zh) * 2015-12-18 2022-01-21 中國大陸商南大光電半導體材料有限公司 合成二矽烷基胺與聚矽烷基胺
US10703915B2 (en) * 2016-09-19 2020-07-07 Versum Materials Us, Llc Compositions and methods for the deposition of silicon oxide films
US10647578B2 (en) * 2016-12-11 2020-05-12 L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude N—H free and SI-rich per-hydridopolysilzane compositions, their synthesis, and applications
US11078569B2 (en) * 2017-09-19 2021-08-03 Versum Materials Us, Llc Trisilylamine derivatives as precursors for high growth rate silicon-containing films

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201500365A (zh) * 2013-06-26 2015-01-01 Air Prod & Chem 氮雜－多矽烷前驅物及包含氮雜－多矽烷前驅物的膜沉積方法

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