TW201522355A - 被胺基取代之三甲矽烷基胺及三乙矽烷基胺化合物及其合成方法 - Google Patents

被胺基取代之三甲矽烷基胺及三乙矽烷基胺化合物及其合成方法 Download PDF

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TW201522355A
TW201522355A TW103133646A TW103133646A TW201522355A TW 201522355 A TW201522355 A TW 201522355A TW 103133646 A TW103133646 A TW 103133646A TW 103133646 A TW103133646 A TW 103133646A TW 201522355 A TW201522355 A TW 201522355A
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Jean-Marc Girard
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Abstract

本說明書描述經由藉由過渡金屬催化劑催化的對應未經取代之三甲矽烷胺與胺之間的脫氫偶合製備之不含鹵素的被胺取代之三甲矽烷基胺及三乙矽烷基胺化合物及其製備方法。此新穎方法係基於Si-H與N-H部分之催化脫氫偶合,形成含有Si-N之化合物及氫氣。該方法可藉由諸如Ru(0)/碳、Pd(0)/MgO之過渡金屬非均相催化劑以及充當均相催化劑之過渡金屬有機金屬錯合物催化。該等含-Si-N之產物不含鹵素。該等化合物可適用於藉由化學氣相沈積或原子層沈積含Si膜來沈積薄膜。

Description

被胺基取代之三甲矽烷基胺及三乙矽烷基胺化合物及其合成方法
本申請案主張2013年9月27日申請之美國臨時專利申請案第61/883,452號之優先權。主張該美國臨時專利申請案之優先權。
在文獻中發現之形成矽-雜原子及鍺-雜原子鍵的大部分製程均涉及氯矽烷與親核試劑(胺、膦等)之反應。此等反應係基於淨脫鹵氫,因而形成一當量鹵化氫,鹵化氫需要鹼來清除,形成大量需要濾出之鹽。此事實亦將反應範疇限制於鹼相容之基板且產生被諸如氯之鹵素及胺基鹵素污染的產物。
諸如甲矽烷、乙矽烷及三甲矽烷之矽烷化合物用於多種應用中。在半導體領域中,矽烷化合物常用作藉由化學氣相沈積(CVD)產生例如氮化矽、氧化矽或氮氧化矽之基於矽之介電或半導體膜的起始物質。更特定言之,矽烷化合物可藉由與含氮反應氣體(諸如氨氣)反應產生氮化矽,藉由與含氧氣體(諸如氧氣)反應產生氧化矽,且藉由與含氮氣體及含氧氣體反應產生氮氧化矽。
目前,藉由CVD產生氮化矽膜之標準方法包含誘發氨氣或其他胺(胺基化合物)與諸如氯矽烷之鹵矽烷(矽烷化合物)之間的反應;然 而,氯化銨或胺鹽酸鹽作為此反應之副產物產生。氯化銨為白色固體,因而累積在CVD反應設備之排氣管線中並阻塞。胺鹽酸鹽為用於電學應用之胺基矽烷中非常不希望的污染物,因為其可與CVD腔室中之金屬反應且使半導體材料之電性質降級或產生其他類型之缺陷。此外,已知此等鹽藉由分解-重組過程昇華,產生HCl。氯化氫為一種腐蝕性氣體,其可破壞在CVD腔室中發生之任何製程以及腔室本身。來自此等或任何其他來源之反應性氯可引起此等有害作用。
在CVD方法中,因此需要具有不含鹵素之起始物質。
圖1為典型反應器設備,其中反應容器為安裝有攪拌器且連接至能夠提供真空及反應物之歧管的高壓釜反應器。
圖2為典型反應器設備,其中反應容器附接至允許氫氣排出之冷凝器及用於移除產物之具有過濾器之汲取管。
已研發一種用於合成具有矽-氮鍵之化合物且不形成鹵素鹽副產物的方法。藉由本文中描述及主張之合成方法產生的所有化合物均「不含鹵素」,如該術語在本文所定義。此方法係基於氫之催化脫氫偶合以形成氣體及氮矽鍵。該製程藉由過渡金屬催化劑催化。催化劑可為非均相或均相的。二級胺之一般反應藉由等式1給出。該一般反應在等式1中給出。等式1之反應為放熱的。反應可在溶劑中或無溶劑下進行。反應可在分批或連續流動反應器中進行。當使用分批反應器時,反應器可附接至被連接至低溫冷阱之冷凝器(圖2)。在此組件中,所形成之氫氣可在反應發生時排出。壓力可藉由附接在冷凝器與低溫冷阱之間的背壓調節器控制。低溫冷阱可連接至排出管線,允許氫氣在反應期間及/或反應之後自系統傳送出。具有過濾器之汲取管允許自容器容易地移除產物。
除非另外指明,否則如本說明書中所用之術語「胺」始終係指二級胺。
1. (H3Si)3N+nHNR1R2+mHNR3R4+kHNR5R6=(R1R2N)n(R3R4N)m(R5R6N)k(NSi3H(9-n-m-k))+(n+m+k+)H2
其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N可為環狀二級胺,包括氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,環狀二級胺包括氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物。
烷基取代基之成員之非限制性清單包含:甲基、乙基、丙基、異丙基、丁基、第三丁基、第二丁基、異丁基、戊基、新戊基、異戊基、己基、異己基。芳基取代基之成員之非限制性清單包含:苯基、甲苯基、二甲苯基、萘基、吡啶基。
烯基定義為藉由移除一個氫原子而衍生自烯烴的任何單價脂族烴基CnH2n-1(諸如2-丁烯基CH3CH:CHCH2-)。其中n=2至8。
炔基定義為具有碳-碳參鍵及通式CnH2n-2之任何系列開鏈烴。其中n=2至8。
視胺化合物之結構及Si化合物之結構以及Si與N之莫耳比而定,可形成多種含有Si-N鍵之分子。此等含有Si-N鍵之分子可為直鏈或分 支鏈。描述直鏈及分支鏈組合及每一者合成方法之實例。
一種具有下式之化合物, (R1R2N)n(R3R4N)m(R5R6N)k(NSi3H(9-n-m-k));其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N可為環狀二級胺,獨立地選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物之群。當R1、R3或R5為H時,胺為一級胺。當R1、R3或R5為氫時,若對應R2、R4或R6獨立地選自直鏈或分支鏈C3至C6烷基、直鏈或分支鏈C3至C8烯基、直鏈或分支鏈C3至C8炔基、C6至C10芳基、直鏈或分支鏈C3至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C3至C6烷基取代之甲矽烷基之群,環狀二級胺包括氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物,則可避免多取 代。
此項技術已描述在本文中所述之通式結構內的化合物。所有此類化合物自本發明之化合物技術方案排除。排除在W.M.Scantlin及A.D.Norman Inorganic Chemistry,第11卷,第12期,3082-3084,1972中發現之以下化合物:[(SiH3)2N]2SiH2
一種製備具有下式之化合物的方法,
其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N可為環狀二級胺,其獨立地選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物之群。當R1、R3或R5為H時,胺為一級胺。當R1、R3或R5為氫時,若對應R2、R4或R6獨立地選自直鏈或分支鏈C3至C6烷基、直鏈或分支鏈C3至C8烯基、直鏈或分支鏈C3至C8炔基、C6至C10芳基、直鏈或分支鏈C3至C6烷基醚、甲矽 烷基、三甲基甲矽烷基或直鏈或分支鏈C3至C6烷基取代之甲矽烷基之群,環狀二級胺包括氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物,則可避免多取代。
a)使反應物TSA及nR1R2NH及mR3R4NH及kR5R6NH在過渡金屬催化劑存在下接觸,形成反應混合物;b)視情況添加溶劑至反應混合物;c)維持反應混合物在約0℃至約250℃之間的溫度下;d)使反應繼續進行,以形成(R1R2N)n(R3R4N)m(R5R6N)k(NSi3H(9-n-m-k));e)自反應混合物分離(R1R2N)n(R3R4N)m(R5R6N)k(NSi3H(9-n-m-k));其中反應混合物溫度可在合成期間變化且經維持使得反應混合物之溫度不降至約0℃以下且不超過約250℃。
一種製備具有下式之化合物的方法, (R1R2N)n(R3R4N)k(R5R6N)m(NSi6H(15-n-m-k))
其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之 群,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N可為環狀二級胺,包括氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物。
a)使反應物TDSA及nR1R2NH及mR3R4NH及kR5R6NH在過渡金屬催化劑存在下接觸,形成反應混合物;b)視情況添加溶劑至反應混合物;c)維持反應混合物在約0℃至約250℃之間的溫度下;d)使反應繼續進行,以形成(R1R2N)n(R3R4N)k(R5R6N)m(NSi6H(15-n-m-k));e)自反應混合物分離產物(R1R2N)n(R3R4N)k(R5R6N)m(NSi6H(15-n-m-k));其中反應溫度可在合成期間變化且經維持使得反應混合物之溫度不降至約0℃以下且不超過約250℃。
一種製備具有下式之化合物的方法,
其中R1、R2獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N可為環狀二級胺,其選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物之群,R3、R4及R5獨立地選自H及直鏈或分支 鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,環狀二級胺選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物之群,其中R係選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚之群。
a)使反應物N[(SiH2R3)(SiH2R4)(SiH2R5)及HNR1R2在過渡金屬催化劑存在下接觸,形成反應混合物;b)視情況添加溶劑至反應混合物;c)維持反應混合物在約0℃至約250℃之間的溫度下;d)使反應繼續進行,以形成N[(SiH2R3)(SiH2R4)(SiHR5 NR1R2)];e)自反應混合物分離產物N[(SiH2R3)(SiH2R4)(SiHR5 NR1R2)];其中反應混合物溫度可在合成期間變化且經維持使得反應混合物之溫度不降至約0℃以下且不超過約250℃。
針對R1及R2=乙基;R3、R4及R5=H之示例結構:
一種製備具有下式之化合物的方法,
a)使反應物TSA及HN(CH2CH3)2在過渡金屬催化劑存在下接觸,形成反應混合物; b)視情況添加溶劑至反應混合物;c)維持反應混合物在約0℃至約250℃之間的溫度下;d)使反應繼續進行,以形成H8Si3N(CH2CH3)2;e)自反應混合物分離H8Si3N(CH2CH3)2;其中反應溫度可在合成期間變化且經維持使得反應混合物之溫度不降至約0℃以下且不超過約250℃。
術語不含氯、不含鹵素、不含胺基氯及不含胺基鹵素在本文用以定義含有低於5ppm鹵素、較佳低於3ppm鹵素且更佳低於1ppm鹵素之化合物。術語鹵素及鹵化物包括氟、氯、溴及碘。在本發明之合成中實現不含鹵素之產物,因為本發明之起始反應物、催化劑及視情況存在之溶劑不含鹵素。術語胺基鹵化物及胺基鹵素係指包括(但不限於)氨及與鹵素締合之有機胺的任何胺。此締合可為鹽、複合物或化學鍵。術語「反應容器」及「反應器」係指相同設備,具有相同含義且在本文中可互換使用。反應器可為用於分批合成之容器或促進連續合成之流過容器。術語「反應混合物」係指反應物、催化劑及視情況存在之溶劑之組合,其中發生反應以形成產物。如本發明及申請專利範圍中所用之術語「不含鹵化物」及「不含鹵素」係指自諸如(但不限於)鹵素離子、結合之鹵素及胺基鹵素之所有來源存在之鹵素含量。
以下方法描述胺基-三甲矽烷基胺之合成,其包含:a)使胺及TSA反應物在過渡金屬催化劑存在下接觸,形成反應混合物;b)視情況添加溶劑至反應混合物;c)維持反應混合物在約0℃至約250℃之間的溫度下;d)使反應繼續進行,以形成產物;e)自反應混合物分離產物; 如本文所用之術語「維持......在溫度下」意指視需要加熱或冷卻以產生在規定最小及最高溫度內之溫度。胺及矽烷添加至反應容器之次序可為胺先或矽烷先。當起始物質不含鹵素時,產物將不含鹵素及胺基鹵素。
適合本發明之非均相催化劑包括過渡金屬催化劑及稀土元素。催化劑係選自由以下組成之群:Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Y、Zr、Nb、Mo、Tc、Ru、Rh、Pd、Ag、Cd、La、Hf、Ta、W、Re、Os、Ir、Pt、Au、Hg、Yb及U。較佳催化劑係選自由Ru、Pd、Rh、Ir、Fe、Ni、Pt、Cr、Cu及Au組成之群。更佳催化劑係選自由Rh、Pd、Ru及Pt組成之群。最佳催化劑為Ru及Ru/碳。另一較佳催化劑為Pd/MgO。
本發明之催化劑較佳黏附於載體。載體為具有高表面積之固體。典型載體材料包括(但不限於):氧化鋁、MgO、沸石、碳、單塊堇青石、矽藻土、矽膠、二氧化矽/氧化鋁、ZrO及TiO2。較佳載體為碳、氧化鋁、二氧化矽及MgO。更佳載體為碳。載體具有在約1m2/g至約3,000m2/g範圍內之BET表面積。較佳範圍為約100m2/g至約2,000m2/g。催化劑之金屬負荷在約0.01重量百分比至約50重量百分比範圍內。較佳範圍為約0.5重量百分比至約20重量百分比。更佳範圍為約0.5重量百分比至約10重量百分比。催化劑可藉由大量已知之方法活化。真空加熱催化劑為一種較佳方法。催化劑可在添加至反應容器前或在反應容器中在添加反應物前活化。
催化劑可含有促進劑。促進劑為本身不為催化劑,但當與活性催化劑少量混合時增加其效率(活性和/或選擇性)之物質。促進劑通常為金屬,諸如Mn、Ce、Mo、Li、Re、Ga、Cu、Ru、Pd、Rh、Ir、Fe、Ni、Pt、Cr、Cu及Au及/或其氧化物。其可分開添加至反應容器或其可為催化劑本身之一部分。舉例來說,Ru/Mn/C(藉由錳促進之 釕/碳)或Pt/CeO2/Ir/SiO2(藉由二氧化鈰及銥促進之鉑/二氧化矽)。一些促進劑本身可充當催化劑,但其與主催化劑組合使用可提高主催化劑之活性。催化劑可充當其他催化劑之促進劑。在此上下文中,該催化劑可稱為雙金屬(或多金屬)催化劑。舉例來說,Ru/Rh/C可稱為釕及銠/碳雙金屬催化劑或藉由銠促進之釕/碳。活性催化劑為充當特定化學反應中之催化劑的材料。
催化劑可需要活化,其通常在真空下或在惰性氣體或還原氣體(諸如氫氣或氦氣)下及高溫下進行。通常催化劑在約125℃下及約-14psig(約1托)下活化。如本文中所用之動態真空描述約1托之真空。活化條件將因所選催化劑而略微變化。用於活化各種催化劑之條件為此項技術中已知。活化催化劑可儲存供將來使用。
當溶劑在本發明中使用時,選擇與反應物不反應之溶劑。溶劑無水且不使催化劑去活化(中毒)。此類溶劑之非限制性清單包括:烷烴,諸如C5至C20直鏈、分支鏈或環狀烷烴及其混合物;烯烴,諸如1-十八烯、環辛二烯及環己烯;氯烷烴,諸如二氯甲烷及二氯乙烷;芳烴,諸如甲苯、二甲苯、均三甲苯及萘(naftalene);及雜環,諸如喹啉及吡啶及其混合物。較佳溶劑為正十八烷。較佳地,應選擇沸點與產物化合物之沸點相差約10℃之溶劑。
本發明中使用之惰性氣體在反應條件下不具反應性。惰性氣體之非限制性清單包括氦氣、氬氣及氮氣。較佳氣體為氦氣。
裝備有機械攪拌器之帕爾高壓釜(Parr autoclave)為適合反應容器。為合成單取代三甲矽烷基胺及單取代三乙矽烷基胺,在開始反應時TSA或TDSA與胺之莫耳比在約0.5至約5範圍內,較佳在約1至約3範圍內。對於多取代TSA及多取代TDSA,在開始反應時TSA或TDSA與胺之莫耳比在約0.1至約0.9範圍內。
術語低溫捕獲意謂氣體物質在低溫冷阱中冷凝。
實例 在加壓反應器中,藉由市售釕/碳催化劑催化的三甲矽烷基胺(TSA)與二乙胺之間的反應合成1-二乙胺基甲矽烷基-雙-乙矽烷基胺:向裝備有機械攪拌器、熱電偶、壓力計及壓力傳感器及3個計量閥之0.3L高壓釜饋入5.3g(0.0025mmol釕)5重量%釕/碳催化劑。隨後反應器在動態真空下在約125℃下加熱3小時。如本文所用之動態真空描述約1托之真空。冷卻至室溫後,添加14.8g(0.202mol)二乙胺至反應器,且接著其在液氮浴中冷卻至約-130℃。40g(0.372mol)三甲矽烷基胺轉移至反應器。隨後反應器逐漸加熱至約100℃。在約400rpm下攪拌65分鐘之後,壓力增加約300psi。壓力增加與形成之氫氣(及產物)量成比例,因此其將視反應規模而變化。當壓力停止增加時反應完成。可能需要在反應完成前使其停止。反應器冷卻至室溫(「RT」)。揮發物收集在SSLB中液氮溫度下之低溫冷阱中。反應器壓力下降至50托。
自反應容器回收1-二乙胺基甲矽烷基-雙-乙矽烷基胺。
所得溶液含有30%(11.3g)二乙胺基甲矽烷基-雙-乙矽烷基胺。未分離產率為30%。
結構:二乙胺基甲矽烷基-雙-乙矽烷基胺:
TSA胺化合物之一般合成:a)在加壓反應器中,藉由過渡金屬催化劑催化的三甲矽烷基胺(TSA)與胺之間的反應合成被胺取代之TSA化合物:向裝備有機械攪拌器、熱電偶、壓力計及壓力傳感器及3個計量閥的高壓釜或類似加壓反應容器饋入過渡金屬催化劑。隨後在動態真空下在約125℃下加 熱反應器3小時,以活化催化劑。催化劑可在添加至反應容器前或在反應容器中在添加反應物前活化。若催化劑在添加至反應容器前活化,則省去在動態真空下在約125℃下預先加熱3小時以活化催化劑的步驟。冷卻至室溫後,添加胺至反應器,且接著其在液氮浴中冷卻至-130℃。將適當量之三甲矽烷基胺轉移至反應器。維持反應器溫度不降至0℃以下且不超過250℃。在攪拌約5分鐘至約2天下,反應器壓力增加直至反應完成。壓力增加與形成之氫氣(及產物)量成比例。因此,反應器壓力將視反應規模、每種反應物之量及反應器尺寸而變化。當壓力停止增加時反應完成。在反應完成之後,反應器冷卻至室溫。揮發物收集在SSLB中液氮溫度下之低溫冷阱中,且反應器壓力降至約40托至約100托之間。
為產生單取代TSA/胺化合物,TSA/胺之莫耳比為約0.5至約5且更佳為約1至約3。為產生多取代TSA/胺化合物,TSA/胺之莫耳比為約0.1至約0.9。比率愈低,TSA化合物上胺之取代度將愈大。
用於合成TSA/胺化合物之較佳催化劑係選自由Ru、Pd、Rh、Ir、Fe、Ni、Pt、Cr、Cu及Au組成之群。最佳催化劑為釕。
TDSA胺化合物之一般合成:a)在加壓反應器中,藉由過渡金屬催化劑催化的三乙矽烷基胺(TDSA)與胺之間的反應合成被胺取代之TDSA化合物:向裝備有機械攪拌器、熱電偶、壓力計及壓力傳感器及3個計量閥的高壓釜或類似加壓反應容器饋入過渡金屬催化劑。隨後在動態真空下在約125℃下加熱反應器3小時,以活化催化劑。催化劑可在添加至反應容器前或在反應容器中在添加反應物前活化。若催化劑在添加至反應容器前活化,則省去在動態真空下在約125℃下預先加熱3小時以活化催化劑的步驟。冷卻至室溫後,添加胺至反應器,且接著其在液氮浴中冷卻至-130℃。將適當量之三甲矽烷基胺轉移至反應器。維持反應器溫度不 降至約0℃以下且不超過約250℃。在攪拌約5分鐘至約2天下,反應器壓力增加直至反應完成。壓力增加與形成之氫氣(及產物)量成比例。因此,反應器壓力將視反應規模、每種反應物之量及反應器尺寸而變化。當壓力停止增加時反應完成。在反應完成之後,反應器冷卻至室溫。揮發物收集在SSLB中液氮溫度下之低溫冷阱中,且反應器壓力降至約40托至約100托之間。
為產生單取代TDSA/胺化合物,TSA/胺之莫耳比為約0.5至約5且更佳為約1至約3。為產生多取代TDSA/胺化合物,TSA/胺之莫耳比為約0.1至約0.9。比率愈低,TDSA化合物上胺之取代度將愈大。
用於合成TDSA/胺化合物之較佳催化劑係選自由Ru、Pd、Rh、Ir、Fe、Ni、Pt、Cr、Cu及Au組成之群。最佳催化劑為釕。
術語「未分離產率」意謂產率藉由稱重反應粗物質且藉由其層析圖估計產物量來確定。術語「分離產率」意謂產物經純化且稱重,其中產率百分比藉由稱重之量佔理論值的百分比確定。
本發明之胺基三甲矽烷基胺及胺基三乙矽烷基胺用作氣相沈積法之前驅體。本文揭示使用所揭示之前驅體用於氣相沈積法之方法。所揭示之方法提供前驅體用於沈積含矽膜之用途。所揭示之方法可適用於製造半導體、光伏打、LCD-TFT或平板型裝置。該方法包括:將所揭示之前驅體之蒸氣引入至其中已安置有至少一個基板的反應器中;且使用氣相沈積製程將至少部分所揭示之前驅體沈積至基板上以形成含Si層。
所揭示之方法亦提供使用氣相沈積製程在基板上形成含有雙金屬之層,且更特定言之,沈積SiMNx及SiMOx膜,其中x為0-4,以及SiMOxNy膜,其中x+y為0至4且M為來自Ta、Hf、Zr、Ti、Ni、Mn、Ge、B、Nb、Mg、Al、Sr、Y、Ba、Ca、As、Sb、Bi、Sn、Pb、Co、鑭系元素(例如Er)或其組合之群的金屬。一般SiMOx、SiMOx或 SiMOxNy術語涵蓋各種相對濃度之Si及M,在約5%至約95%之Si/(Si+M)範圍內。
所揭示之在基板上形成含矽層之方法可適用於製造半導體、光伏打、LCD-TFT或平板型裝置。所揭示之前驅體可使用此項技術中已知之任何氣相沈積法沈積含Si膜。適合氣相沈積法之實例包括化學氣相沈積(CVD)或原子層沈積(ALD)。示例性CVD方法包括熱CVD、電漿增強CVD(PECVD)、脈衝CVD(PCVD)、低壓CVD(LPCVD)、低於大氣壓CVD(SACVD)或大氣壓CVD(APCVD)、熱絲CVD(HWCVD,亦稱為催化-CVD,其中熱絲充當沈積製程之能量來源)、遠距電漿CVD(RP-CVD)、UV輔助之CVD、流動式CVD(FCVD)、自由基併入之CVD及其組合。示例性ALD方法包括熱ALD、電漿增強ALD(PEALD)、空間隔離ALD、熱絲ALD(HWALD)、自由基併入之ALD、UV輔助之ALD及其組合。亦可使用超臨界流體沈積。所揭示之方法亦可用於頒予Applied Materials,Inc.之美國專利申請公開案第2014/0051264號(其內容全文併入本文中)中所描述之流動式PECVD沈積製程中。沈積方法較佳為ALD、空間ALD、PE-ALD或流動式CVD(F-CVD)。
前驅體蒸氣引入含有至少一個基板之反應室中。反應室內之溫度及壓力以及基板之溫度保持在適合於將至少部分前驅體氣相沈積至基板上之條件下。換言之,在汽化前驅體引入腔室中之後,腔室內之條件使得至少部分汽化前驅體沈積至基板上以形成含矽膜。共反應物亦可用於幫助形成含Si層。共反應物可與前驅體同時或分開依序引入,且選自O2、O3、O自由基及離子、NO、N2O、H2O、H2O2、CO2、CO、羧酸、福馬林、醇、二醇、NH3、肼(經取代或未經取代,例如UDMH、第三丁基肼)、胺(例如DMA、TMA、DEA、TEA、TB、NH2)、二胺、N自由基及離子、H2及其混合物。
反應室可為其中發生沈積法之裝置的任何殼體或腔室,諸如(不限於)平行板型反應器、冷壁型反應器、熱壁型反應器、單晶圓反應器、多晶圓反應器或其他該等類型之沈積系統,例如空間ALD腔室、卷輪式ALD腔室。所有此等示例性反應室均能夠用作ALD或CVD反應室。反應室可維持在約1毫托至約760托範圍內之壓力下。此外,反應室內之溫度可在約20℃至約600℃範圍內。一般技術者應認識到可僅僅經由實驗優化溫度以達成所要結果。
反應器之溫度可藉由控制基板固持器之溫度、控制反應器壁之溫度或控制基板本身之溫度來控制。用於加熱基板之裝置為此項技術中已知。加熱反應器壁至充足溫度以獲得在足夠生長速率下且具有所要物理狀態及組成之所要膜。反應器壁可加熱至的非限制性示例性溫度範圍包括約20℃至約600℃。當利用電漿沈積製程時,沈積溫度可在約20℃至約550℃範圍內。或者,當執行熱製程時,沈積溫度可在約200℃至約600℃範圍內。
或者,基板可加熱至充足溫度以獲得在充足生長速率下且具有所要物理狀態及組成之所要含矽膜。基板可加熱至的非限制性示例性溫度範圍包括150℃至600℃。較佳地,基板溫度保持低於或等於500℃。
上面將沈積含矽膜之基板的類型將視預期最終用途而變化。基板一般定義為上面進行製程之材料。基板可為用於半導體、光伏打、平板或LCD-TFT裝置製造之任何適合之基板。適合基板之實例包括晶圓,例如矽、二氧化矽、玻璃、Ge或GaAs晶圓。晶圓可具有自先前製造步驟在其上沈積之一或多層不同材料。舉例而言,晶圓可包括矽層(晶體、非晶形、多孔等)、氧化矽層、氮化矽層、氮氧化矽層、碳摻雜氧化矽(SiCOH)層、多孔碳摻雜氧化矽層、碳氮化矽、氫化碳化矽或其組合。此外,晶圓可包括銅層、鎢層或金屬層(例如鉑、鈀、鎳、銠、金、鈷、鍺、銻、碲、錫、釕及其合金)。晶圓可包括障壁 層,例如錳、氧化錳、Ta、W、Ti、V、Zr、Hg、Nb、Mo、Mn及Ru之氮化物。氮化物可為摻雜C之氮化物。亦可使用諸如聚(3,4-伸乙二氧基噻吩)聚(苯乙烯磺酸)[PEDOT:PSS]之塑膠層。膜可沈積在例如光阻層、非晶碳層或聚醯亞胺膜之有機膜上。層可為平面的或經圖案化。在一些實施例中,基板可包括氧化物層,其用作MIM、DRAM、RERAM、相變RAM或FeRam技術中之介電材料(例如Zr、Hg、Ti、Nb、Mo、Al、Ta、鑭系元素、稀土元素及其混合三元或二元芳基氧化物);或來自基於氮化物之膜(例如TaN),其用作銅與低k層之間的黏附障壁。所揭示之製程可直接將含矽層沈積在晶圓上或直接沈積在晶圓頂上之一個或一個以上(當經圖案化層形成基板時)層上。此外,一般技術者將認識到本文所用之術語「膜」或「層」係指放在或擴散在表面上之一定厚度之一些材料且表面可具有3D圖案或微觀結構,例如孔洞及溝槽或線。沈積可選擇性針對基板上之特定區域,或選擇性針對某些暴露材料。舉例而言,生長可在用自配向單層(「SAM」)覆蓋之基板之某些部分上抑制。在本說明書及申請專利範圍中,晶圓及上面之任何締合層稱為基板。
所揭示之前驅體可呈純形式或呈與例如甲苯、乙苯、二甲苯、均三甲苯、癸烷、十二烷、辛烷、己烷、戊烷、三級胺、四氫呋喃、乙基甲基酮、十氫萘或其他溶劑之適合溶劑之摻合物提供。所揭示之前驅體可以不同濃度存在於溶劑中。舉例而言,所得濃度可在約0.05M至約2M範圍內。
純或摻合前驅體藉由習知方式(例如導管及/或流量計)以蒸氣形式引入反應器中。蒸氣形式之前驅體可藉由經由諸如鼓泡、蒸氣或藉由使用昇華器(Xu等人在PCT公開案WO2009/087609中揭示的一種昇華器)之習知汽化步驟汽化純或摻合前驅體溶液產生。純或摻合前驅體可以液態饋送至汽化器,在汽化器中在將其引入反應器之前將其汽 化(直接液體注射)。當存在時,載氣可包括(但不限於)Ar、He、N2或H2及其混合物。接著,載氣及前驅體以蒸氣形式引入反應器中。
必要時,容器可加熱至允許前驅體呈其液相或固相且具有充足蒸氣壓之溫度。容器可維持在例如0-150℃範圍內之溫度下。熟習此項技術者認識到容器溫度可按已知方式調節以控制所汽化之前驅體之蒸氣壓及製程腔室中之濃度。
藉由氣相沈積法獲得之膜可藉由例如退火、反應性退火、UV固化、電子束固化及自由基退火之各種方法進一步處理。膜組成及結構可受此步驟顯著影響。
應瞭解,在如所附申請專利範圍中所表述之本發明原理及範疇內,熟習此項技術者可對本文中已描述且說明以便解釋本發明之性質的細節、材料、步驟及部件配置作出許多其他改變。因此,本發明並不意欲限於以上所提供之實例及/或隨附圖式中的特定實施例。
雖然以上描述含有許多特殊性,但此等不應解釋為限制本發明之範疇,而是僅僅提供本發明之一些較佳實施例之說明。各種其他實施例及衍生物可在其範疇內。應瞭解,在如所附申請專利範圍中所表述之本發明原理及範疇內,熟習此項技術者可對本文中已描述且說明以便解釋本發明之性質的細節、材料、步驟及部件配置作出許多其他改變。

Claims (17)

  1. 一種具有下式之化合物, 其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N R1R2N、R3R4N及R5R6N可為環狀二級胺,其獨立地選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或該環狀二級胺之任何C取代之衍生物之群,且排除具有式C18H48N4Si3、C15H41N3Si3、C6H21NSi3及C7H23NSi3之化合物,該等化合物排除以下已知之化合物:[(SiH3)2N]2SiH2
  2. 一種具有下式之化合物, 其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N R1R2N、R3R4N及R5R6N可為環狀二級胺,其獨立地選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或該環狀二級胺之任何C取代之衍生物之群。
  3. 一種具有下式之化合物, 其中:R1、R2獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基 或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R3、R4及R5獨立地選自H及直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,環狀二級胺選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或該環狀二級胺之任何C取代之衍生物,R1R2N可為環狀二級胺,其選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或環狀二級胺之任何C取代之衍生物之群,其中R係選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚之群。
  4. 如請求項3之化合物,其具有下式: 其中R1及R2=乙基;R3、R4及R5=H。
  5. 如請求項3之化合物,其中R1、R2獨立地選自由H、甲基、乙基、異丙基及第三丁基組成之群;或NR1R2為具有3至8個碳原子之環狀飽和或不飽和環狀胺,當R1為H時,R2不可為甲基或乙基。
  6. 如請求項3之化合物,其中R1、R2為乙基。
  7. 一種製備如請求項1之化合物之方法,其包含:a)使反應物TSA及(R1R2NH)n及(R3R4NH)m及(R5R6NH)k在過渡金屬催化劑存在下接觸,形成反應混合物; b)視情況添加溶劑至該反應混合物;c)維持該反應混合物在約0℃至約250℃之間的溫度下;d)使該反應繼續進行,以形成(R1R2N)n(R3R4N)m(R5R6N)k(NSi3H(9-n-m-k));e)自該反應混合物分離該(R1R2N)n(R3R4N)m(R5R6N)k(NSi3H(9-n-m-k));其中該反應混合物溫度可在合成期間變化且經維持使得該反應混合物之溫度不降至約0℃以下且不超過約250℃。
  8. 如請求項5之方法,其中該催化劑係選自由以下組成之群:Ru、Pd、Rh、Ir、Fe、Ni、Pt、Cr、Cu及Au。
  9. 一種製備如請求項2之化合物之方法,其包含:a)使反應物TDSA及(R1R2NH)n及(R3R4NH)m及(R5R6NH)k在過渡金屬催化劑存在下接觸,形成反應混合物;b)視情況添加溶劑至該反應混合物;c)維持該反應混合物在約0℃至約250℃之間的溫度下;d)使該反應繼續進行,以形成(R1R2N)n(R3R4N)k(R5R6N)m(Nsi6H8H(3-k)H(3-m);e)自該反應混合物分離該產物(R1R2N)n(R3R4N)k(R5R6N)m(NSi3H8H(3-k)H(3-m);其中該反應溫度可在合成期間變化且經維持使得該反應混合物之溫度不降至約0℃以下且不超過約250℃。
  10. 如請求項7之方法,其中該催化劑係選自由以下組成之群:Ru、Pd、Rh、Ir、Fe、Ni、Pt、Cr、Cu及Au。
  11. 一種製備如請求項3之化合物之方法,其包含:a)使反應物N[(SiH2R3)(SiH2R4)(SiH2R5)]及HNR1R2在過渡金屬催化劑存在下接觸,形成反應混合物;b)視情況添加溶劑至該反應混合物; c)維持該反應混合物在約0℃至約250℃之間的溫度下; d)使該反應繼續進行,以形成N[(SiH2R3)(SiH2R4)(SiHR5 NR1R2)];e)自該反應混合物分離該產物N[(SiH2R3)(SiH2R4)(SiHR5 NR1R2)];其中該反應混合物溫度可在合成期間變化且經維持使得該反應混合物之溫度不降至約0℃以下且不超過約250℃。
  12. 如請求項9之方法,其中該催化劑係選自由以下組成之群:Ru、Pd、Rh、Ir、Fe、Ni、Pt、Cr、Cu及Au。
  13. 一種具有下式之不含鹵素之化合物, 其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N R1R2N、R3R4N及R5R6N可為環狀二級胺,其獨立 地選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或該環狀二級胺之任何C取代之衍生物之群,其中鹵素之可偵測量低於5ppm,且排除具有式C18H48N4Si3、C15H41N3Si3、C6H21NSi3及C7H23NSi3之化合物,且其中鹵素之可偵測量低於5ppm。
  14. 一種具有下式之不含鹵素之化合物, 其中n=1至3;m=0至3;k=0至3;R1、R3及R5獨立地選自H、直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R2、R4及R6獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N、R3R4N及R5R6N R1R2N、R3R4N及R5R6N可為環狀二級胺,其獨立地選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或該環狀二級胺之任何C取代之衍生物之群且其中鹵素之可偵測量低於5ppm。
  15. 一種具有下式之不含鹵素之化合物, 其中R1、R2獨立地選自直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,R1R2N可為環狀二級胺,其選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或該環狀二級胺之任何C取代之衍生物之群,R3、R4及R5獨立地選自H及直鏈或分支鏈C1至C6烷基、直鏈或分支鏈C1至C8烯基、直鏈或分支鏈C1至C8炔基、C6至C10芳基、直鏈或分支鏈C1至C6烷基醚、甲矽烷基、三甲基甲矽烷基或直鏈或分支鏈C1至C6烷基取代之甲矽烷基之群,環狀二級胺選自氮丙啶、氮雜環丁烷、哌啶、吡咯啶、吡咯、咪唑、吡唑、吲哚或該環狀二級胺之任何C取代之衍生物之群,其中鹵素之可偵測量低於5ppm。
  16. 一種藉由氣相沈積來沈積含Si薄膜之方法,其中該前驅化合物係選自如請求項1、2、3、4之化合物及[(SiH3)2N]2SiH2之群。
  17. 如請求項14之方法,其中該氣相沈積製程係選自ALD、PEALD或FCVD。
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