TWI596436B - 含有含二酮結構之有機基之含矽光阻下層膜形成組成物 - Google Patents
含有含二酮結構之有機基之含矽光阻下層膜形成組成物 Download PDFInfo
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- TWI596436B TWI596436B TW101102878A TW101102878A TWI596436B TW I596436 B TWI596436 B TW I596436B TW 101102878 A TW101102878 A TW 101102878A TW 101102878 A TW101102878 A TW 101102878A TW I596436 B TWI596436 B TW I596436B
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- INCPMRSWRODNTN-UHFFFAOYSA-N trichloro-$l^{3}-chlorane Chemical compound ClCl(Cl)Cl INCPMRSWRODNTN-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- G03F7/36—Imagewise removal not covered by groups G03F7/30 - G03F7/34, e.g. using gas streams, using plasma
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
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Description
本發明係關於用於製造半導體裝置之基板與光阻(例如光阻、電子線光阻)之間形成下層膜用的組成物。更詳細而言係關於半導體裝置製造的微影步驟中,形成用於光阻下層之下層膜之微影用光阻下層膜形成組成物。此外係有關使用該下層膜形成組成物之光阻圖型之形成方法。
以往製造半導體裝置時,藉由使用光阻的微影進行微細加工。前述微細加工係於矽晶圓等之半導體基板上形成光阻的薄膜,其上介於描繪有半導體裝置之圖型的光罩圖型,照射紫外線等之活性光線,經顯像後,將所得之光阻圖型作為保護膜,對基板進行蝕刻處理,於基板表面形成與前述圖型對應之微細凹凸的加工法。但是近年,半導體裝置之高度積體度化進展,所使用的活性光線有由KrF準分子雷射(248nm)至ArF準分子雷射(193nm)之短波長化的傾向。隨著此傾向,活性光線由半導體基板之反射的影響成為大問題。
又,作為半導體基板與光阻之間的下層膜,使用作為含有矽或鈦等金屬元素之硬光罩為人所知的膜(例如參照專利文獻1)。此時,在光阻與硬光罩,在構成成分上具有較大的差異,因此彼等藉由乾蝕刻而除去的速度係大部分取決於使用於乾蝕刻之氣體種類。而藉由適當選擇氣體
種類,不會伴隨光阻膜厚之較大的減少,可藉由蝕刻除去硬光罩。如此,近年之半導體裝置製造時,首先為了達成反射防止效果及種種效果,故於半導體基板與光阻之間配置光阻下層膜。至今雖檢討光阻下層膜用之組成物,但是因該被要求特性之多樣性等,期待開發光阻下層膜用之新材料。
例如由具有含有酸不安定基之二酯結構之矽烷所得之聚矽氧烷材料使用於微影製程(參照專利文獻2)。
[專利文獻1]日本特開平11-258813號公報
[專利文獻2]日本特開2007-226170號公報
本發明之目的係提供可用於製造半導體裝置之微影用光阻下層膜形成組成物。詳細而言係提供形成可作為硬光罩使用之光阻下層膜用的微影用光阻下層膜形成組成物。此外,提供形成可作為反射防止膜使用之光阻下層膜用之微影用光阻下層膜形成組成物。另外,提供不會引起與光阻之相互混合,且與光阻比較,具有較大乾蝕刻速度之微影用光阻下層膜及形成該下層膜用的光阻下層膜形成組成物。
本發明之目的係提供可改善圖型化之光阻膜之圖型形
狀之光阻下層膜形成用的光阻下層膜形成組成物。
本發明之目的係提供使用前述光阻下層膜形成組成物之半導體裝置之製造方法。
本發明係第1觀點為一種微影用光阻下層膜形成組成物,其特徵係含有作為矽烷之水解性有機矽烷、其水解物、或其水解縮合物,該矽烷為含有下述式(1):【化1】〔(R1)aSi(R2)(3-a)〕b(R3) 式(1)
[式中R3係式(2)、式(3)、或式(4):
(式(2)、式(3)及式(4)之各式中,R4、R5及R6之中至少一個為單鍵、或作為連結基之與矽原子鍵結的基團,R4為未與矽原子鍵結時,R4係表示氫原子、或烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、胺
基或氰基之有機基、或彼等之組合,R5與R6未與矽原子鍵結時,R5與R6係分別獨立表示直鎖烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、胺基或氰基之有機基、或彼等之組合,R4、R5或R6之任一為作為連結基之與矽原子鍵結的基團時,與該矽原子鍵結之基團係各自表示由上述定義之基團中去除1個氫原子之2價基。但是式(3)中之R6、式(4)中之R5及式(4)中之R6為與矽原子鍵結時,不為單鍵,表示作為連結基之與矽原子鍵結的基團)表示的基團,R1係分別獨立表示烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、胺基或氰基的有機基、或彼等之組合。R2係分別獨立表示烷氧基、醯氧基、或鹵素原子。a係表示0~2之整數,b係表示1~3之整數]所表示的水解性有機矽烷。
第2觀點為如上述第1觀點之微影用光阻下層膜形成組成物,其中前述水解性有機矽烷為含有式(5):【化3】R1 aSi(R2)4-a 式(5)(式中R1係分別獨立表示烷基、芳基、芳烷基、鹵化烷
基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、烷氧基芳基、醯氧基芳基或氰基之有機基、或彼等之組合,且藉由Si-C鍵與矽原子鍵結的基團,R2係分別獨立表示烷氧基、醯氧基、或鹵素原子,a係表示0~3之整數)表示之有機矽化合物及式(6):【化4】〔R1 cSi(R2)3-c〕2Yb 式(6)(式中,R1係表示烷基,R2係分別獨立表示烷氧基、醯氧基、或鹵素原子,Y係表示伸烷基或伸芳基,b係表示0或1之整數,c係表示0或1之整數)表示之有機矽化合物所成群中選出之至少1種的有機矽化合物與上述式(1)表示之水解性有機矽烷之組合、彼等之水解物及彼等之水解縮合物所成群中選出之至少1種。
第3觀點為如第1或2觀點之微影用光阻下層膜形成組成物,其中含有上述式(1)表示之水解性有機矽烷之水解縮合物、或上述式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之水解縮合物作為聚合物。
第4觀點為如第1~3觀點中任一觀點之微影用光阻下層膜形成組成物,其中上述式(1)表示之水解性有機矽烷為具有8.00~20.00之pKa值者。
第5觀點為如第1~4觀點中任一觀點之微影用光阻下
層膜形成組成物,其係再含有酸作為水解觸媒。
第6觀點為如第1~5觀點中任一觀點之微影用光阻下層膜形成組成物,其係再含有水。
第7觀點為一種光阻下層膜,其特徵係將如第1~6觀點中任一觀點之微影用光阻下層膜形成組成物塗佈於半導體基板上,藉由燒成而得者。
第8觀點為一種半導體裝置之製造方法,其特徵係含有以下步驟:將如第1~6觀點中任一觀點之微影用光阻下層膜形成組成物塗佈於半導體基板上,經燒成形成光阻下層膜的步驟;在前述下層膜之上塗佈光阻膜形成組成物,形成光阻膜的步驟;使前述光阻膜曝光的步驟;曝光後,使該光阻膜顯像,得到圖型化之光阻膜的步驟;遵循該圖型化之光阻膜,蝕刻光阻下層膜得到圖型化之光阻下層膜的步驟;及遵循該圖型化之光阻膜與圖型化之光阻下層膜,對半導體基板進行加工的步驟。
第9觀點為一種半導體裝置之製造方法,其特徵係含有以下步驟:於半導體基板上形成有機下層膜的步驟;其上塗佈如第1~6觀點中任一觀點之微影用光阻下層膜形成組成物,經燒成形成光阻下層膜的步驟;
在前述光阻下層膜之上塗佈光阻膜形成組成物,形成光阻膜的步驟;使前述光阻膜曝光的步驟;曝光後,使該光阻膜顯像,得到圖型化之光阻膜的步驟;遵循該圖型化之光阻膜,蝕刻光阻下層膜得到圖型化之光阻下層膜的步驟;遵循該圖型化之光阻下層膜,蝕刻有機下層膜的步驟及遵循該圖型化之有機下層膜,對半導體基板進行加工的步驟。
本發明之光阻下層膜形成組成物係含有水解性有機矽烷,因此由該組成物所形成的光阻下層膜係因具有聚有機矽氧烷結構,因此對於氧系乾蝕刻氣體具有充分的耐乾蝕刻性,基板(或有機下層膜)之加工時,可作為硬光罩使用。
又,由本發明之光阻下層膜形成組成物所形成的光阻下層膜可作為反射防止膜使用,且不會引起與光阻之相互混合,與光阻比較,具有較大乾蝕刻速度者。
又,由本發明之光阻下層膜形成組成物所形成的光阻下層膜,其被納入構成該下層膜之聚合物中的有機基為具有特定值之酸性度的結構,因此可改善藉由圖型化所得之
光阻膜的圖型形狀者。
又,藉由本發明之製造方法時,由前述光阻下層膜形成組成物所形成的膜作為光阻下層膜使用,可適合製造半導體裝置。
以下詳細說明本發明之特徵。
本發明係藉由塗佈法於基板上形成光阻下層膜,或介於基板上之有機下層膜,藉由塗佈法於其上形成光阻下層膜,再於該光阻下層膜上形成光阻膜(例如光阻、電子線光阻)。其次藉由曝光及顯像形成光阻圖型,再使用該光阻圖型,對光阻下層膜進行乾蝕刻進行圖型轉印,藉由該圖型進行基板加工,或蝕刻有機下層膜進行圖型轉印,藉由該有機下層膜對基板進行加工。
形成微細圖型時,為了防止圖型倒塌,光阻膜厚有變薄的傾向。因光阻薄膜化,為了將圖型轉印於存在於其下層之膜上的乾蝕刻,若蝕刻速度未高於上層膜時,則無法圖型轉印。本發明中,基板上介於有機下層膜或不介於有機下層膜,依序於其上被覆本發明之光阻下層膜(含有無機系矽系化合物),再於其上被覆光阻膜(有機光阻膜)。有機系成份的膜及無機系成份的膜會因蝕刻氣體的選擇,造成乾蝕刻速度極大差異,其中有機系成份的膜使用氧系氣體時,乾蝕刻速度變快,無機系成份的膜使用含鹵素氣體時,乾蝕刻速度變快。
例如形成光阻圖型後,將存在於其下層之本發明的光阻下層膜使用含有鹵素氣體進行乾蝕刻,將圖型轉印於光阻下層膜,以轉印於該光阻下層膜之圖型,使用含有鹵素之氣體進行基板加工。或使用被圖型轉印之光阻下層膜,以氧系氣體乾蝕刻該下層之有機下層膜,將圖型轉印於有機下層膜,再以該被圖型轉印之有機下層膜,使用含有鹵素之氣體,進行基板加工。
本發明中,該光阻下層膜為具有硬光罩之功能者,上述式(1)之結構中之烷氧基或醯氧基、鹵素原子等水解性基會水解或部分水解,其後藉由矽烷醇基之縮合反應形成聚矽氧烷結構的聚合物。此聚有機矽氧烷結構具有作為硬光罩之充分的功能。
聚有機矽氧烷結構(中間膜)係對於存在於其下之有機下層膜之蝕刻或基板加工(蝕刻)時作為硬光罩。即,對於基板加工時及有機下層膜之氧系乾蝕氣體,具有充分的耐乾蝕性者。
本發明之光阻下層膜具備提升對於此等上層光阻之乾蝕刻速度及基板加工時等的耐乾蝕刻性者。
本發明之光阻下層膜形成組成物所成的光阻下層膜係含有具有1-3二酮結構、其二酮結構之異構物之乙醇結構、1-3酮酯結構、1-3二酯結構之矽烷而形成。此等係至少含有1-3二酮的結構,必須含有此結構。因具有此等結構,藉由與存在於上層之光阻膜的相乘效果,可防止圖型形狀成為底腳(Footing),而得到直接圖型形狀(straight-
pattern-shape)。此乃是由於存在於1-3二酮結構之α位之氫原子的酸性度所造成的。具有這種酸性度的重要性係在上層之光阻曝光時發揮效果。
此酸性度高(pKa值低)可改善圖型形狀。但是此酸性度太高時,光阻下層膜形成組成物產生凝膠化,故不佳。
又,這種至少具有1-3二酮結構的有機基必須被納入聚合物中,為了被納入聚合物中,因此以含有水解性矽烷之有機基的形態較佳。藉由被納入聚合物中,可防止形成下層膜之過程之燒成造成的燒失。
其次,說明本發明之組成物的構成。
本發明係含有作為矽烷之水解性有機矽烷、其水解物、或其水解縮合物,該矽烷為含有下述式(1)表示之水解性有機矽烷的微影用光阻下層膜形成組成物。
矽烷整體中對矽原子之式(2)表示之部分結構的比例為未達50莫耳%,例如可含有0.5~30莫耳%、0.5~25莫耳%、0.5~15莫耳%、或0.5~10莫耳%的比例。
本發明之光阻下層膜形成組成物係包含式(1)表示之水解性有機矽烷、其水解物、或其水解縮合物與溶劑。也可含有作為任意成分之酸、水、醇、硬化觸媒、酸產生劑、其他有機聚合物、吸光性化合物及界面活性劑等。
本發明之光阻下層膜形成組成物中之固形分,例如為0.1~50質量%、或0.1~30質量%、0.1~25質量%。其中固形分係指由光阻下層膜形成組成物之全成分中除去溶劑成
分者。
固形分中所佔有之水解性有機矽烷、其水解物、及其水解縮合物的比例係20質量%以上,例如有50~100質量%、60~100質量%、70~100質量%。
本發明用的水解性有機矽烷係具有式(1)表示的結構。
式(1)中之R3係式(2)、式(3)、或式(4)表示的基團。式(1)中之R1係分別獨立表示烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、胺基或氰基的有機基、或彼等之組合。R2係分別獨立表示烷氧基、醯氧基、或鹵素原子。a係表示0~2之整數,b係表示1~3之整數。
式(2)、式(3)及式(4)之各式中,R4、R5及R6之中至少一個為單鍵、或與作為連結基之矽原子鍵結的基團,R4為未與矽原子鍵結時,R4係表示氫原子、或烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、胺基或氰基之有機基、或彼等之組合,R5與R6未與矽原子鍵結時,R5與R6係分別獨立表示直鏈烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、胺基或氰基之有機基、或彼等之組合,R4、R5或R6之任一為作為連結基之與矽原子鍵結的
基團時,與該矽原子鍵結之基團係各自表示由上述定義之基團中去除1個氫原子的2價基。但是式(3)中之R6、式(4)中之R5及式(4)中之R6為與矽原子鍵結時,不為單鍵,表示作為連結基之與矽原子鍵結的基團。
上述連結基可使用例如烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、胺基或氰基的有機基、或對應彼等之組合之2價有機基。
上述烷基係具有直鏈或分枝之碳原子數1~10的烷基,例如有甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、1-甲基-正丁基、2-甲基-正丁基、3-甲基-正丁基、1,1-二甲基-正丙基、1,2-二甲基-正丙基、2,2-二甲基-正丙基、1-乙基-正丙基、正己基、1-甲基-正戊基、2-甲基-正戊基、3-甲基-正戊基、4-甲基-正戊基、1,1-二甲基-正丁基、1,2-二甲基-正丁基、1,3-二甲基-正丁基、2,2-二甲基-正丁基、2,3-二甲基-正丁基、3,3-二甲基-正丁基、1-乙基-正丁基、2-乙基-正丁基、1,1,2-三甲基-正丙基、1,2,2-三甲基-正丙基、1-乙基-1-甲基-正丙基及1-乙基-2-甲基-正丙基等。也可使用環狀烷基,例如碳原子數1~10的環狀烷基,例如有環丙基、環丁基、1-甲基-環丙基、2-甲基-環丙基、環戊基、1-甲基-環丁基、2-甲基-環丁基、3-甲基-環丁基、1,2-二甲基-環丙基、2,3-二甲基-環丙基、1-乙基-環丙基、2-乙基-環丙基、環己基、1-甲基-環戊基、2-甲基-環戊基、3-甲基-
環戊基、1-乙基-環丁基、2-乙基-環丁基、3-乙基-環丁基、1,2-二甲基-環丁基、1,3-二甲基-環丁基、2,2-二甲基-環丁基、2,3-二甲基-環丁基、2,4-二甲基-環丁基、3,3-二甲基-環丁基、1-正丙基-環丙基、2-正丙基-環丙基、1-異丙基-環丙基、2-異丙基-環丙基、1,2,2-三甲基-環丙基、1,2,3-三甲基-環丙基、2,2,3-三甲基-環丙基、1-乙基-2-甲基-環丙基、2-乙基-1-甲基-環丙基、2-乙基-2-甲基-環丙基及2-乙基-3-甲基-環丙基等。
直鏈烷基係碳原子數1~10的烷基,例如有甲基、乙基、正丙基、正丁基、正戊基、正己基等。
芳基例如有碳原子數6~20的芳基,例如有苯基、鄰-甲基苯基、間-甲基苯基、對-甲基苯基、鄰-氯苯基、間-氯苯基、對-氯苯基、鄰-氟苯基、對-氫硫基苯基、鄰-甲氧基苯基、對-甲氧基苯基、對-胺基苯基、對-氰基苯基、α-萘基、β-萘基、鄰-聯苯基、間-聯苯基、對-聯苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基及9-菲基。
烯基例如有碳原子數2~10之烯基,例如有乙烯基、1-丙烯基、2-丙烯基、1-甲基-1-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-正丙基乙烯基、1-甲基-1-丁烯基、1-甲基-2-丁烯基、1-甲基-3-丁烯基、2-乙基-2-丙烯基、2-甲基-1-丁烯基、2-甲基-2-丁烯基、
2-甲基-3-丁烯基、3-甲基-1-丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1-異丙基乙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-環戊烯基、2-環戊烯基、3-環戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、1-甲基-2-戊烯基、1-甲基-3-戊烯基、1-甲基-4-戊烯基、1-正丁基乙烯基、2-甲基-1-戊烯基、2-甲基-2-戊烯基、2-甲基-3-戊烯基、2-甲基-4-戊烯基、2-正丙基-2-丙烯基、3-甲基-1-戊烯基、3-甲基-2-戊烯基、3-甲基-3-戊烯基、3-甲基-4-戊烯基、3-乙基-3-丁烯基、4-甲基-1-戊烯基、4-甲基-2-戊烯基、4-甲基-3-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1-甲基-2-乙基-2-丙烯基、1-第二丁基乙烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、1-異丁基乙烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、2-異丙基-2-丙烯基、3,3-二甲基-1-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、1-正丙基-1-丙烯基、1-正丙基-2-丙烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-第三丁基乙烯基、1-甲基-1-乙基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基、1-異丙基-1-丙烯基、1-異丙基-2-丙烯基、1-甲基-2-環戊烯基、1-甲基-3-環戊烯基、
2-甲基-1-環戊烯基、2-甲基-2-環戊烯基、2-甲基-3-環戊烯基、2-甲基-4-環戊烯基、2-甲基-5-環戊烯基、2-亞甲基-環戊基、3-甲基-1-環戊烯基、3-甲基-2-環戊烯基、3-甲基-3-環戊烯基、3-甲基-4-環戊烯基、3-甲基-5-環戊烯基、3-亞甲基-環戊基、1-環己烯基、2-環己烯基及3-環己烯基等。
芳烷基係被芳基取代的烷基,例如有被苯基取代之碳原子數1~碳原子數10之烷基,具體例有苄基、乙基苯基、丙基苯基、丁基苯基等。
又,經此等氟、氯、溴或碘等之鹵素原子所取代的有機基。
具有環氧基之有機基,例如有環氧丙氧基甲基、環氧丙氧基乙基、環氧丙氧基丙基、環氧丙氧基丁基、環氧基環己基等。
具有丙烯醯基之有機基,例如有丙烯醯基甲基、丙烯醯基乙基、丙烯醯基丙基等。
具有甲基丙烯醯基之有機基,例如有甲基丙烯醯基甲基、甲基丙烯醯基乙基、甲基丙烯醯基丙基等。
具有氫硫基之有機基,例如有乙基氫硫基、丁基氫硫基、己基氫硫基、辛基氫硫基等。
具有氰基之有機基,例如有氰乙基、氰丙基等。
具有磺醯基之有機基,例如有甲基磺醯基、烯丙基磺醯基、苯基磺醯基等。
式(1)中之烷氧基係碳原子數1~20之烷氧基,具體
而言,例如有碳原子數1~20之具有直鏈、支鏈、環狀之烷基部分的烷氧基,例如有甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、正戊氧基(amyloxy)、1-甲基-正丁氧基、2-甲基-正丁氧基、3-甲基-正丁氧基、1,1-二甲基-正丙氧基、1,2-二甲基-正丙氧基、2,2-二甲基-正丙氧基、1-乙基-正丙氧基、正己氧基、1-甲基-正戊氧基、2-甲基-正戊氧基、3-甲基-正戊氧基、4-甲基-正戊氧基、1,1-二甲基-正丁氧基、1,2-二甲基-正丁氧基、1,3-二甲基-正丁氧基、2,2-二甲基-正丁氧基、2,3-二甲基-正丁氧基、3,3-二甲基-正丁氧基、1-乙基-正丁氧基、2-乙基-正丁氧基、1,1,2-三甲基-正丙氧基、1,2,2-三甲基-正丙氧基、1-乙基-1-甲基-正丙氧基及1-乙基-2-甲基-正丙氧基等,又環狀之烷氧基,例如有環丙氧基、環丁氧基、1-甲基-環丙氧基、2-甲基-環丙氧基、環戊氧基、1-甲基-環丁氧基、2-甲基-環丁氧基、3-甲基-環丁氧基、1,2-二甲基-環丙氧基、2,3-二甲基-環丙氧基、1-乙基-環丙氧基、2-乙基-環丙氧基、環己氧基、1-甲基-環戊氧基、2-甲基-環戊氧基、3-甲基-環戊氧基、1-乙基-環丁氧基、2-乙基-環丁氧基、3-乙基-環丁氧基、1,2-二甲基-環丁氧基、1,3-二甲基-環丁氧基、2,2-二甲基-環丁氧基、2,3-二甲基-環丁氧基、2,4-二甲基-環丁氧基、3,3-二甲基-環丁氧基、1-正丙基-環丙氧基、2-正丙基-環丙氧基、1-異丙基-環丙氧基、2-異丙基-環丙氧基、1,2,2-三甲基-環丙氧基、1,2,3-三甲基-環丙氧基、2,2,3-
三甲基-環丙氧基、1-乙基-2-甲基-環丙氧基、2-乙基-1-甲基-環丙氧基、2-乙基-2-甲基-環丙氧基及2-乙基-3-甲基-環丙氧基等。
式(1)中之醯氧基係碳原子數2~20之醯氧基,例如有甲基羰氧基、乙基羰氧基、正丙基羰氧基、異丙基羰氧基、正丁基羰氧基、異丁基羰氧基、第二丁基羰氧基、第三丁基羰氧基、正戊基羰氧基、1-甲基-正丁基羰氧基、2-甲基-正丁基羰氧基、3-甲基-正丁基羰氧基、1,1-二甲基-正丙基羰氧基、1,2-二甲基-正丙基羰氧基、2,2-二甲基-正丙基羰氧基、1-乙基-正丙基羰氧基、正己基羰氧基、1-甲基-正戊基羰氧基、2-甲基-正戊基羰氧基、3-甲基-正戊基羰氧基、4-甲基-正戊基羰氧基、1,1-二甲基-正丁基羰氧基、1,2-二甲基-正丁基羰氧基、1,3-二甲基-正丁基羰氧基、2,2-二甲基-正丁基羰氧基、2,3-二甲基-正丁基羰氧基、3,3-二甲基-正丁基羰氧基、1-乙基-正丁基羰氧基、2-乙基-正丁基羰氧基、1,1,2-三甲基-正丙基羰氧基、1,2,2-三甲基-正丙基羰氧基、1-乙基-1-甲基-正丙基羰氧基、1-乙基-2-甲基-正丙基羰氧基、苯基羰氧基及甲苯磺醯基羰氧基等。
式(1)中之鹵素原子,例如有氟、氯、溴、碘等。
上述式(1)表示之水解性有機矽烷可使用pKa為8.00~20.00、或8.00~13.00之範囲者。上述pKa為8.00以下時,酸性度太高,安定性低。又,pKa超過20.00時,在微影步驟無法形成良好的光阻圖型。
上述式(1)表示之水解性有機矽烷係式(2)表示之結構,例如有以下所例示。
上述式(1)表示之水解性有機矽烷可使用式(2)表
示之結構為酮型為以異構物、乙醇型形態存在者。
上述式(1)表示之水解性有機矽烷係式(3)表示之結構,例如有以下所例示。
上述式(1)表示之水解性有機矽烷係式(4)表示之結構,例如有以下所例示。
本發明可包含選自式(5)表示之有機矽化合物及式(6)表示之有機矽化合物所成群之至少1種的有機矽化合物與上述式(1)表示之水解性有機矽烷之組合、彼等之水解物、或彼等之水解縮合物。
又,本發明可使用上述式(1)表示之水解性有機矽烷之水解縮合物、或式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之水解縮合物。
本發明可合併使用式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物。
即可合併使用式(1)表示之水解性有機矽烷、其水解物、或其水解縮合物與式(5)表示之有機矽化合物、其水解物、或其水解縮合物。
上述式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之比例,可以莫耳比表示在1:0~1:200之範圍內使用。為了得到良好的光阻形狀時,式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之比例,可以莫耳比表示在1:199~1:2之範圍內使用。
此等可作為水解縮合物(聚有機矽氧烷之聚合物)使用較佳,較佳為使用式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之水解縮合物(聚有機矽氧烷之聚合物)。
式(5)表示之有機矽化合物中之R1係分別獨立表示烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、烷氧基芳基、醯氧基芳基或氰基之有機基、或彼等之組合,且藉由Si-C鍵與矽原子鍵結的基團,R2係分別獨立表示烷氧基、醯氧基、或鹵素原子,a係表示0~3之整數。
R1及R2表示之烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、烷氧基芳基、醯氧基芳基或氰基之有機基、及水解性基所含的烷氧基、醯氧基、或鹵素原子以上述式(1)所記載者。
以式(5)表示之有機矽化合物,例如有四甲氧基矽烷、四氯矽烷、四乙醯氧基矽烷、四乙氧基矽烷、四正丙氧基矽烷、四異丙氧基矽烷、四正丁氧基矽烷、四乙醯氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三氯矽烷、甲基三乙醯氧基矽烷、甲基三丙氧基矽烷、甲基三丁氧基矽烷、甲基三戊氧基矽烷、甲基三苯氧基矽烷、甲基三苄氧基矽烷、甲基三苯乙氧基矽烷、環氧丙氧基甲基三甲氧基矽烷、環氧丙氧基甲基三乙氧基矽烷、α-環氧丙氧基乙基三甲氧基矽烷、α-環氧丙氧基乙基三乙氧基矽烷、β-環氧丙氧基乙基三甲氧基矽烷、β-環氧丙氧基乙基三乙氧基矽烷、α-環氧丙氧基丙基三甲氧基矽烷、α-環氧丙氧基丙基三乙氧基矽烷、β-環氧丙氧基丙基三甲氧基矽烷、β-環氧丙氧基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、γ-環氧丙氧基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三丙氧基矽烷、γ-環氧丙氧基丙基三丁氧基矽烷、γ-環氧丙氧基丙基三苯氧基矽烷、α-環氧丙氧基丁基三甲氧基矽烷、α-環氧丙氧基丁基三乙氧基矽烷、β-環氧丙氧基丁基三乙氧基矽烷、γ-環氧丙氧基丁基三甲氧基矽烷、γ-環氧丙氧基丁基三乙氧基矽烷、δ-環氧丙氧基丁基三甲氧基矽烷、δ-環氧丙氧基丁基三乙氧基矽烷、(3,4-環氧基環己基)甲基三甲氧基矽烷、(3,4-環氧基環己基)甲基三乙氧基矽烷、β-(3,4-環氧基環己基)乙基三甲氧基矽烷、β-(3,4-環氧基環己基)乙基三乙氧基矽烷、β-(3,4-環氧基環己基)乙基三丙氧基矽烷、β-(3,4-環氧
基環己基)乙基三丁氧基矽烷、β-(3,4-環氧基環己基)乙基三苯氧基矽烷、γ-(3,4-環氧基環己基)丙基三甲氧基矽烷、γ-(3,4-環氧基環己基)丙基三乙氧基矽烷、δ-(3,4-環氧基環己基)丁基三甲氧基矽烷、δ-(3,4-環氧基環己基)丁基三乙氧基矽烷、環氧丙氧基甲基甲基二甲氧基矽烷、環氧丙氧基甲基甲基二乙氧基矽烷、α-環氧丙氧基乙基甲基二甲氧基矽烷、α-環氧丙氧基乙基甲基二乙氧基矽烷、β-環氧丙氧基乙基甲基二甲氧基矽烷、β-環氧丙氧基乙基乙基二甲氧基矽烷、α-環氧丙氧基丙基甲基二甲氧基矽烷、α-環氧丙氧基丙基甲基二乙氧基矽烷、β-環氧丙氧基丙基甲基二甲氧基矽烷、β-環氧丙氧基丙基乙基二甲氧基矽烷、γ-環氧丙氧基丙基甲基二甲氧基矽烷、γ-環氧丙氧基丙基甲基二乙氧基矽烷、γ-環氧丙氧基丙基甲基二丙氧基矽烷、γ-環氧丙氧基丙基甲基二丁氧基矽烷、γ-環氧丙氧基丙基甲基二苯氧基矽烷、γ-環氧丙氧基丙基乙基二甲氧基矽烷、γ-環氧丙氧基丙基乙基二乙氧基矽烷、γ-環氧丙氧基丙基乙烯基二甲氧基矽烷、γ-環氧丙氧基丙基乙烯基二乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三氯矽烷、乙烯基三乙醯氧基矽烷、乙烯基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三氯矽烷、苯基三乙醯氧基矽烷、苯基三乙氧基矽烷、γ-氯丙基三甲氧基矽烷、γ-氯丙基三乙氧基矽烷、γ-氯丙基三乙醯氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、γ-甲基丙烯氧基丙基三甲氧基矽烷、γ-氫硫基丙基三
甲氧基矽烷、γ-氫硫基丙基三乙氧基矽烷、β-氰基乙基三乙氧基矽烷、氯甲基三甲氧基矽烷、氯甲基三乙氧基矽烷、二甲基二甲氧基矽烷、苯基甲基二甲氧基矽烷、二甲基二乙氧基矽烷、苯基甲基二乙氧基矽烷、γ-氯丙基甲基二甲氧基矽烷、γ-氯丙基甲基二乙氧基矽烷、二甲基二乙醯氧基矽烷、γ-甲基丙烯氧基丙基甲基二甲氧基矽烷、γ-甲基丙烯氧基丙基甲基二乙氧基矽烷、γ-氫硫基丙基甲基二甲氧基矽烷、γ-氫硫基甲基二乙氧基矽烷、甲基乙烯基二甲氧基矽烷、甲基乙烯基二乙氧基矽烷、苯基磺醯基胺丙基三乙氧基矽烷、甲基磺醯基胺丙基三乙氧基矽烷、苯基磺醯基胺丙基三甲氧基矽烷、甲基磺醯基胺丙基三甲氧基矽烷等。
式(6)表示之有機矽化合物之R1係表示烷基,R2係分別獨立表示烷氧基、醯氧基、或鹵素原子,Y係表示伸烷基或伸芳基,b係表示0或1之整數,c係表示0或1之整數。
式(6)係表示b為0時,表示2個矽原子進行單鍵結的有機矽化合物,b表示1時,表示介於伸烷基或伸芳基,而2個矽原子進行鍵結的有機矽化合物。
上述烷基、烷氧基、醯氧基、或鹵素原子可使用式(1)所例示者。又,伸烷基、伸芳基例如有與上述烷基及芳基對應之2價有機基。
式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之水解縮合物的具體例,如以下所例示。
式(1)表示之水解性有機矽烷之水解縮合物(聚有機矽氧烷)、或式(1)表示之水解性有機矽烷與式(5)及/或式(6)表示之有機矽化合物之水解縮合物(聚有機矽氧烷)可得到重量平均分子量1000~1000000、或1000~100000的縮合物。此等分子量係藉由GPC分析,以聚苯乙烯換算所得的分子量。
GPC之測定條件,例如可使用GPC裝置(商品名HLC-8220GPC,東曹股份有限公司製),GPC管柱(商品名Shodex KF803L、KF802、KF801、昭和電工製),管柱溫度為40℃,洗提液(溶出溶劑)使用四氫呋喃,流量(流速)為1.0ml/min,標準試料可使用聚苯乙烯(昭和電工股份有限公司製)進行測定。
烷氧基矽烷基、醯氧基矽烷基或鹵化矽烷基之水解時,當水解性基1莫耳時,使用0.5~100莫耳,較佳為1~10莫耳的水。
又,水解性基1莫耳時,可使用0.001~10莫耳,較佳為0.001~1莫耳的水解觸媒。
進行水解與縮合時的反應溫度通常為20~80℃。
水解可完全水解或部分水解。即,水解縮合物中可殘留水解物或單體。水解、縮合時,可使用觸媒。
水解觸媒例如有金屬螯合化合物、有機酸、無機酸、有機鹼、無機鹼。
作為水解觸媒之金屬螯合化合物,例如有三乙氧基‧單(乙醯丙酮)鈦、三正丙氧基‧單(乙醯丙酮)鈦、三
異丙氧基‧單(乙醯丙酮)鈦、三正丁氧基‧單(乙醯丙酮)鈦、三第二丁氧基‧單(乙醯丙酮)鈦、三第三丁氧基‧單(乙醯丙酮)鈦、二乙氧基‧雙(乙醯丙酮)鈦、二正丙氧基‧雙(乙醯丙酮)鈦、二異丙氧基‧雙(乙醯丙酮)鈦、二正丁氧基‧雙(乙醯丙酮)鈦、二第二丁氧基‧雙(乙醯丙酮)鈦、二第三丁氧基‧雙(乙醯丙酮)鈦、單乙氧基‧三(乙醯丙酮)鈦、單正丙氧基‧三(乙醯丙酮)鈦、單異丙氧基‧三(乙醯丙酮)鈦、單正丁氧基‧三(乙醯丙酮)鈦、單第二丁氧基‧三(乙醯丙酮)鈦、單第三丁氧基‧三(乙醯丙酮)鈦、四(乙醯丙酮)鈦、三乙氧基‧單(乙醯乙酸乙酯)鈦、三正丙氧基‧單(乙醯乙酸乙酯)鈦、三異丙氧基‧單(乙醯乙酸乙酯)鈦、三正丁氧基‧單(乙醯乙酸乙酯)鈦、三第二丁氧基‧單(乙醯乙酸乙酯)鈦、三第三丁氧基‧單(乙醯乙酸乙酯)鈦、二乙氧基‧雙(乙醯乙酸乙酯)鈦、二正丙氧基‧雙(乙醯乙酸乙酯)鈦、二異丙氧基‧雙(乙醯乙酸乙酯)鈦、二正丁氧基‧雙(乙醯乙酸乙酯)鈦、二第二丁氧基‧雙(乙醯乙酸乙酯)鈦、二第三丁氧基‧雙(乙醯乙酸乙酯)鈦、單乙氧基‧三(乙醯乙酸乙酯)鈦、單正丙氧基‧三(乙醯乙酸乙酯)鈦、單異丙氧基‧三(乙醯乙酸乙酯)鈦、單正丁氧基‧三(乙醯乙酸乙酯)鈦、單第二丁氧基‧三(乙醯乙酸乙酯)鈦、單第三丁氧基‧三(乙醯乙酸乙酯)鈦、四(乙醯乙酸乙酯)鈦、單(乙醯丙酮)三(乙醯乙酸乙酯)鈦、雙(乙醯丙酮)雙(乙
醯乙酸乙酯)鈦、三(乙醯丙酮)單(乙醯乙酸乙酯)鈦等之鈦螯合化合物,三乙氧基‧單(乙醯丙酮)鋯、三正丙氧基‧單(乙醯丙酮)鋯、三異丙氧基‧單(乙醯丙酮)鋯、三正丁氧基‧單(乙醯丙酮)鋯、三第二丁氧基‧單(乙醯丙酮)鋯、三第三丁氧基‧單(乙醯丙酮)鋯、二乙氧基‧雙(乙醯丙酮)鋯、二正丙氧基‧雙(乙醯丙酮)鋯、二異丙氧基‧雙(乙醯丙酮)鋯、二正丁氧基‧雙(乙醯丙酮)鋯、二第二丁氧基‧雙(乙醯丙酮)鋯、二第三丁氧基‧雙(乙醯丙酮)鋯、單乙氧基‧三(乙醯丙酮)鋯、單正丙氧基‧三(乙醯丙酮)鋯、單異丙氧基‧三(乙醯丙酮)鋯、單正丁氧基‧三(乙醯丙酮)鋯、單第二丁氧基‧三(乙醯丙酮)鋯、單第三丁氧基‧三(乙醯丙酮)鋯、四(乙醯丙酮)鋯、三乙氧基‧單(乙醯乙酸乙酯)鋯、三正丙氧基‧單(乙醯乙酸乙酯)鋯、三異丙氧基‧單(乙醯乙酸乙酯)鋯、三正丁氧基‧單(乙醯乙酸乙酯)鋯、三第二丁氧基‧單(乙醯乙酸乙酯)鋯、三第三丁氧基‧單(乙醯乙酸乙酯)鋯、二乙氧基‧雙(乙醯乙酸乙酯)鋯、二正丙氧基‧雙(乙醯乙酸乙酯)鋯、二異丙氧基‧雙(乙醯乙酸乙酯)鋯、二正丁氧基‧雙(乙醯乙酸乙酯)鋯、二第二丁氧基‧雙(乙醯乙酸乙酯)鋯、二第三丁氧基‧雙(乙醯乙酸乙酯)鋯、單乙氧基‧三(乙醯乙酸乙酯)鋯、單正丙氧基‧三(乙醯乙酸乙酯)鋯、單異丙氧基‧三(乙醯乙酸乙酯)鋯、單正丁氧基‧三(乙醯
乙酸乙酯)鋯、單第二丁氧基‧三(乙醯乙酸乙酯)鋯、單第三丁氧基‧三(乙醯乙酸乙酯)鋯、四(乙醯乙酸乙酯)鋯、單(乙醯丙酮)三(乙醯乙酸乙酯)鋯、雙(乙醯丙酮)雙(乙醯乙酸乙酯)鋯、三(乙醯丙酮)單(乙醯乙酸乙酯)鋯等之鋯螯合化合物;三(乙醯丙酮)鋁、三(乙醯乙酸乙酯)鋁等之鋁螯合化合物等。
作為水解觸媒的有機酸,例如有乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、草酸、馬來酸、甲基丙二酸、己二酸、癸二酸、棓酸、丁酸、苯六甲酸、花生浸烯酸、莽草酸(shikimic acid)、2-乙基己酸、油酸、硬脂酸、亞油酸、亞麻酸、水楊酸、苯甲酸、對-胺基苯甲酸、對-甲苯磺酸、苯磺酸、單氯乙酸、二氯乙酸、三氯乙酸、三氟乙酸、甲酸、丙二酸、磺酸、酞酸、富馬酸、檸檬酸、酒石酸等。
作為水解觸媒之無機酸,例如有鹽酸、硝酸、硫酸、氟酸、磷酸等。
作為水解觸媒之有機鹼,例如有吡啶、吡咯、哌嗪、吡咯烷、哌啶、甲基吡啶、三甲胺、三乙胺、單乙醇胺、二乙醇胺、二甲基單乙醇胺、單甲基二乙醇胺、三乙醇胺、二氮雜二環辛烷、二氮雜二環壬烷、二氮雜二環十一烯、四甲基銨氫氧化物等。無機鹼例如有氨、氫氧化鈉、氫氧化鉀、氫氧化鋇、氫氧化鈣等。此等水解觸媒中,較佳為金屬螯合化合物、有機酸、無機酸,此等觸媒可使用1種或2種以上同時使用。
水解所使用的有機溶劑,例如有正戊烷、異戊烷、正己烷、異己烷、正庚烷、異庚烷、2,2,4-三甲基戊烷、正辛烷、異辛烷、環己烷、甲基環己烷等之脂肪族烴系溶劑;苯、甲苯、二甲苯、乙基苯、三甲基苯、甲基乙基苯、正丙基苯、異丙基苯、二乙基苯、異丁基苯、三乙基苯、二異丙基苯、正戊基萘、三甲基苯等之芳香族烴系溶劑;甲醇、乙醇、正丙醇、異丙醇、正丁醇、異丁醇、第二丁醇、第三丁醇、正戊醇、異戊醇、2-甲基丁醇、第二戊醇、第三戊醇、3-甲氧基丁醇、正己醇、2-甲基戊醇、第二己醇、2-乙基丁醇、第二庚醇、庚醇-3、正辛醇、2-乙基己醇、第二辛醇、正壬醇、2,6-二甲基庚醇-4、正癸醇、sec-十一烷醇、三甲基壬醇、sec-十四烷醇、sec-十七烷醇、酚、環己醇、甲基環己醇、3,3,5-三甲基環己醇、苄醇、苯基甲基甲醇、雙丙酮醇、甲酚等之一元醇系溶劑;乙二醇、丙二醇、1,3-丁二醇、戊二醇-2,4、2-甲基-2,4-戊二醇、2,5-己二醇、2,4-庚二醇、2-乙基-1,3-己二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、甘油等之多元醇系溶劑;丙酮、甲基乙基酮、甲基正丙基酮、甲基正丁基酮、二乙基酮、甲基異丁基酮、甲基正戊基酮、乙基正丁基酮、甲基正己基酮、二異丁基酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊二酮、丙酮基丙酮、二丙酮醇、苯乙酮、葑酮等之酮系溶劑;乙醚、異丙醚、正丁醚、正己醚、2-乙基己醚、環氧乙烷、1,2-環氧丙烷、二氧雜環戊烷、4-甲基二氧雜環戊烷、二噁烷、二甲基二噁烷、乙
二醇單甲醚、乙二醇單乙醚、乙二醇二乙醚、乙二醇單正丁醚、乙二醇單正己醚、乙二醇單苯醚、乙二醇單-2-乙基丁醚、乙二醇二丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇二乙醚、二乙二醇單正丁醚、二乙二醇二正丁醚、二乙二醇單正己醚、乙氧基三甘醇、丁二醇二正丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、丙二醇單丁醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單丙醚、二丙二醇單丁醚、三丙二醇單甲醚、四氫呋喃、2-甲基四氫呋喃等之醚系溶劑;碳酸二乙酯、乙酸甲酯、乙酸乙酯、γ-丁內酯、γ-戊內酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸異丁酯、乙酸第二丁酯、乙酸正戊酯、乙酸第二戊酯、乙酸3-甲氧基丁酯、乙酸甲基戊酯、乙酸2-乙基丁酯、乙酸2-乙基己酯、乙酸苄酯、乙酸環己酯、乙酸甲基環己酯、乙酸正壬酯、乙醯乙酸甲酯、乙醯乙酸乙酯、乙酸乙二醇單甲醚、乙酸乙二醇單乙醚、乙酸二乙二醇單甲醚、乙酸二乙二醇單乙醚、乙酸二乙二醇單正丁醚、乙酸丙二醇單甲醚、乙酸丙二醇單乙醚、乙酸丙二醇單丙醚、乙酸丙二醇單丁醚、乙酸二丙二醇單甲醚、乙酸二丙二醇單乙醚、二乙酸乙二醇、乙酸甲氧基三甘醇、丙酸乙酯、丙酸正丁酯、丙酸異戊酯、草酸二乙酯、草酸二正丁酯、乳酸甲酯、乳酸乙酯、乳酸正丁酯、乳酸正戊酯、丙二酸二乙酯、酞酸二甲酯、酞酸二乙酯等之酯系溶劑;N-甲基甲醯胺、N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、乙醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基
丙醯胺、N-甲基吡咯烷酮等之含氮系溶劑;二甲基硫、二乙基硫、噻吩、四氫噻吩、二甲亞碸、環丁碸、1,3-丙磺內酯等之含硫系溶劑等。此等溶劑可使用1種或組合2種以上使用。
其中從溶液之保存安定性的觀點,較佳為丙酮、甲基乙基酮、甲基-n-丙基酮、甲基-n-丁基酮、二乙基酮、甲基-i-丁酮、甲基-n-戊酮、乙基-n-丁酮、甲基-n-己酮、二-i-丁酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊二酮、丙酮基丙酮、雙丙酮醇、苯乙酮、葑酮(1,1,3-三甲基-2-降莰烯)等酮系溶劑。
本發明之光阻下層膜形成組成物可含有硬化觸媒。硬化觸媒係將含有由水解縮合物所構成之聚有機矽氧烷之塗佈膜進行加熱硬化時,具有硬化觸媒的功用。
硬化觸媒可使用銨鹽、膦類、鏻鹽、鋶鹽。
銨鹽例如有具有式(D-1):
(但是m為2~11之整數,n為2~3的整數,R1為烷基或芳基,Y-為陰離子)所表示之構造的第4級銨鹽、具有以式(D-2):
【化13】R2R3R4R5N+Y- 式(D-2)
(但是R2、R3、R4及R5為烷基或芳基,N為氮原子,Y-為陰離子,且R2、R3、R4及R5各自為藉由C-N鍵與氮原子鍵結者)所表示的構造之第4級銨鹽、具有式(D-3):
(但是R6及R7為烷基或芳基,Y-為陰離子)所表示的構造之第4級銨鹽,具有式(D-4):
(但是R8為烷基或芳基,Y-為陰離子)所表示的構造之第4級銨鹽,具有式(D-5):
(但是R9及R10為烷基或芳基,Y-為陰離子)所表示的構造之第4級銨鹽,具有式(D-6):
(但是m為2~11之整數,n為2~3的整數,H為氫原子,Y-為陰離子)所表示的構造之第3級銨鹽。
又,鏻鹽例如有以式(D-7):【化18】R11R12R13R14P+ Y- 式(D-7)
(但是R11、R12、R13及R14係表示烷基或芳基,P為磷原子,Y-為陰離子,且R11、R12、R13及R14各自係藉由C-P鍵與磷原子鍵結)所表示的第4級鏻鹽。
又,前述鋶鹽例如有以式(D-8)【化19】R15R16R17S+Y- 式(D-8)
(式中,R15、R16及R17係表示烷基或芳基,S係表示硫原子,Y-係表示陰離子,R15、R16及R17係分別藉由C-S鍵與硫原子鍵結者)表示之第3級鋶鹽。
上述式(D-1)表示之化合物係由胺衍生的第4級銨鹽,m為2~11之整數,n為2~3之整數。此第4級銨鹽之R1係表示碳原子數1~18,較佳為2~10之烷基或芳基,例如乙基、丙基、丁基等直鏈烷基,或苄基、環己基、環己基甲基、二環戊二烯基等。又陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等的酸基。
上述(D-2)表示之化合物係以R2R3R4R5N+Y-所表示的第4級銨鹽。此第4級銨鹽之R2、R3、R4及R5為碳原子數1~18之烷基或芳基或藉由Si-C鍵與矽原子鍵結的矽烷化合物。陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等的酸基。此第4級銨鹽可由市售品取得,例如有四甲基銨乙酸鹽、四丁基銨乙酸鹽、氯化三乙基苄基銨、溴化三乙基苄基銨、氯化三辛基甲基銨、氯化三丁基苄基銨、氯化三甲基苄基銨等。
上述式(D-3)表示之化合物係由1-取代咪唑衍生的
第4級銨鹽,R6及R7係碳原子數1~18,R6及R7之碳原子數之總和較佳為7以上。例如R6為甲基、乙基、丙基、苯基、苄基,R7為苄基、辛基、十八烷基。陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等酸基。此化合物可由市售品取得,例如可由1-甲基咪唑、1-苄基咪唑等咪唑系化合物與苄基溴、甲基溴等鹵化烷基或鹵化芳基反應而製得。
上述式(D-4)表示之化合物係由吡啶衍生的第4級銨鹽,R8為碳原子數1~18,較佳為碳原子數4~18之烷基或芳基,例如有丁基、辛基、苄基、月桂基。陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等酸基。此化合物可由市售品取得,又例如可由吡啶與月桂基氯、苄基氯、苄基溴、甲基溴、辛基溴等鹵化烷基或鹵化芳基反應而製得。此化合物例如有氯化N-月桂基吡啶鎓、溴化N-苄基吡啶鎓等。
上述式(D-5)表示之化合物係由皮考啉等所代表的取代吡啶衍生之第4級銨鹽,R9為碳原子數1~18,較佳為4~18之烷基或芳基,例如有甲基、辛基、月桂基、苄基等。R10為碳原子數1~18之烷基或芳基,例如為由皮考啉衍生的第4級銨時,R10表示甲基。陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等
酸基。此化合物可由市售品取得,又例如可由皮考啉等取代吡啶與甲基溴、辛基溴、月桂基氯、苄基氯、苄基溴等鹵化烷基或鹵化芳基反應而製得。此化合物例如有N-苄基皮考啉鎓氯化物、N-苄基皮考啉鎓溴化物、N-月桂基皮考啉鎓氯化物等。
上述式(D-6)表示之化合物係由胺衍生的第3級銨鹽,m為2~11之整數,n為2~3之整數。又陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等酸基。可由胺與羧酸或酚等弱酸反應而製得。羧酸例如有甲酸或乙酸,使用甲酸時,陰離子(Y-)為(HCOO-),使用乙酸時,陰離子(Y-)為(CH3COO-)。又使用酚時,陰離子(Y-)為(C6H5O-)。
上述式(D-7)表示之化合物係具有R11R12R13R14P+Y-之構造的第4級鏻鹽。R11、R12、R13及R14係碳原子數1~18之烷基或芳基,或藉由Si-C鍵與矽原子鍵結的矽烷化合物,較佳為R11~R14之4個取代基內,3個為苯基或被取代的苯基,例如有苯基或甲苯基,而剩餘之1個為碳原子數1~18的烷基、芳基或藉由Si-C鍵與矽原子鍵結的矽烷化合物。又陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等酸基。此化合物可由市售品取得,例如有鹵化四n-丁基鏻、鹵化四n-丙基鏻等鹵化四烷基鏻、鹵化三乙基苄基鏻等鹵化三烷基苄基鏻、
鹵化三苯基甲基鏻、鹵化三苯基乙基鏻等鹵化三苯基單烷基鏻、鹵化三苯基苄基鏻、鹵化四苯基鏻、鹵化三甲苯基單芳基鏻、或鹵化三甲苯基單烷基鏻(鹵原子為氯原子或溴原子)。特佳為鹵化三苯基甲基鏻、鹵化三苯基乙基鏻等鹵化三苯基單烷基鏻、鹵化三苯基苄基鏻等鹵化三苯基單芳基鏻、鹵化三甲苯基單苯基鏻等鹵化三甲苯基單芳基鏻、或鹵化三甲苯基單甲基鏻等鹵化三甲苯基單烷基鏻(鹵原子為氯原子或溴原子)。
又,膦類例如有甲基膦、乙基膦、丙基膦、異丙基膦、異丁基膦、苯基膦等伯膦(primary phosphine)、二甲基膦、二乙基膦、二異丙基膦、二異戊基膦、二苯基膦等二代膦、三甲基膦、三乙基膦、三苯基膦、甲苯二苯基膦、二甲基苯基膦等季膦。
上述式(D-8)表示之化合物係具有R15R16R17S+Y-之構造的第3級鋶鹽。R15、R16及R17係碳原子數1~18之烷基或芳基,或藉由Si-C鍵與矽原子鍵結的矽烷化合物,較佳為R15~R17之4個取代基內,3個為苯基或被取代的苯基,例如有苯基或甲苯基,而剩餘之1個為碳原子數1~18的烷基或芳基。又陰離子(Y-)例如有氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等鹵離子,或羧酸根(-COO-)、硫酸根(-SO3 -)、醇鹽(-O-)等酸基。此化合物可由市售品取得,例如有鹵化三n-丁基鋶、鹵化三n-丙基鋶等之鹵化三烷基鋶;鹵化二乙基苄基鋶等之鹵化二烷基苄基鋶;鹵化二苯基甲基鋶、鹵化二苯基乙基鋶等之
鹵化二苯基單烷基鋶;鹵化三苯基鋶(鹵素原子為氯原子或溴原子);三n-丁基鋶羧酸鹽、三n-丙基鋶羧酸鹽基等之三烷基鏻羧酸鹽;二乙基苄基鋶羧酸鹽等之二烷基苄基鋶羧酸鹽;二苯基甲基鋶羧酸鹽、二苯基乙基鋶羧酸鹽等之二苯基單烷基鋶羧酸鹽;三苯基鋶羧酸鹽及此等鹵化物。特佳為鹵化三苯基鋶、三苯基鋶羧酸鹽。
相對於聚有機矽氧烷100質量份,硬化觸媒為0.01~10質量份,或0.01~5質量份,或0.01~3質量份。
將水解性有機矽烷在溶劑中使用觸媒進行水解、縮合所得之水解縮合物(聚合物),可藉由減壓蒸餾等同時去除副產物之醇及使用的水解觸媒或水。又,可藉由中和或離子交換去除水解所用的酸及鹼觸媒。本發明之微影用光阻下層膜形成組成物中,為了使含有該水解縮合物之光阻下層膜形成組成物安定化,可添加有機酸、水、醇或彼等之組合。
上述有機酸例如有草酸、丙二酸、甲基丙二酸、琥珀酸、馬來酸、蘋果酸、酒石酸、酞酸、檸檬酸、戊二酸、乳酸、水楊酸等。其中較佳為草酸、馬來酸等。相對於縮合物(聚有機矽氧烷)100質量份,添加之有機酸係0.5~5.0質量份。又添加之水可使用純水、超純水、離子交換水等,相對於光阻下層膜形成組成物100質量份,其添加量係1~20質量份。
又添加之醇較佳為塗佈後經加熱易飛散者,例如有甲醇、乙醇、丙醇、異丙醇、丁醇等。相對於光阻下層膜形
成組成物100質量份,添加的醇為1~20質量份。
本發明之微影用光阻下層膜形成組成物除了上述成份,必要時可含有有機聚合物化合物、光酸產生劑及界面活性劑等。
藉由使用有機聚合物化合物,可調整由本發明之微影用光阻下層膜形成組成物形成的光阻下層膜之乾蝕刻速度(每單位時間之膜厚的減少量)、衰減係數及折射率等。
有機聚合物化合物並無特別限制,可使用各種有機聚合物。可使用縮聚合聚合物及加成聚合聚合物等。可使用聚酯、聚苯乙烯、聚醯亞胺、丙烯酸聚合物、甲基丙烯酸聚合物、聚乙烯醚、苯酚酚醛清漆、萘酚酚醛清漆、聚醚、聚醯胺、聚碳酸酯等加成聚合聚合物及縮聚合聚合物。較佳為使用具有吸光部位功能之苯環、萘環、蒽環、三嗪環、喹啉環及喹喔啉環等具有芳香環構造的有機聚合物。
這種有機聚合物化合物,例如含有苄基丙烯酸酯、苄基甲基丙烯酸酯、苯基丙烯酸酯、萘基丙烯酸酯、蒽基甲基丙烯酸酯、蒽基甲基甲基丙烯酸酯、苯乙烯、羥基苯乙烯、苄基乙烯醚及N-苯基馬來醯胺等加成聚合性單體作為其結構單位的加成聚合聚合物,或苯酚酚醛清漆、萘酚酚醛清漆等縮聚合聚合物。
使用加成聚合聚合物作為有機聚合物化合物時,其聚合物化合物可為單獨聚合物或共聚物。製造加成聚合聚合物時使用加成聚合性單體。這種加成聚合性單體例如有丙烯酸、甲基丙烯酸、丙烯酸酯化合物、甲基丙烯酸酯化合
物、丙烯醯胺化合物、甲基丙烯醯胺化合物、乙烯基化合物、苯乙烯化合物、馬來醯亞胺化合物、馬來酸酐、丙烯腈等。
丙烯酸酯化合物例如有甲基丙烯酸酯、乙基丙烯酸酯、正己基丙烯酸酯、異丙基丙烯酸酯、環己基丙烯酸酯、苄基丙烯酸酯、苯基丙烯酸酯、蒽基甲基丙烯酸酯、2-羥基乙基丙烯酸酯、3-氯-2-羥基丙基丙烯酸酯、2-羥基丙基丙烯酸酯、2,2,2-三氟乙基丙烯酸酯、2,2,2-三氯乙基丙烯酸酯、2-溴乙基丙烯酸酯、4-羥基丁基丙烯酸酯、2-甲氧基乙基丙烯酸酯、四氫糠基丙烯酸酯、5-丙烯醯氧基-6-羥基降茨烯-2-羧基-6-內酯、3-丙烯醯氧基丙基三乙氧基矽烷及縮水甘油基丙烯酸酯等。
甲基丙烯酸酯化合物例如有甲基甲基丙烯酸酯、乙基甲基丙烯酸酯、正己基甲基丙烯酸酯、異丙基甲基丙烯酸酯、環己基甲基丙烯酸酯、苄基甲基丙烯酸酯、苯基甲基丙烯酸酯、蒽基甲基甲基丙烯酸酯、2-羥基乙基甲基丙烯酸酯、2-羥基丙基甲基丙烯酸酯、2,2,2-三氟乙基甲基丙烯酸酯、2,2,2-三氯乙基甲基丙烯酸酯、2-溴乙基甲基丙烯酸酯、4-羥基丁基甲基丙烯酸酯、2-甲氧基乙基甲基丙烯酸酯、四氫糠基甲基丙烯酸酯、5-甲基丙烯醯氧基-6-羥基降茨烯-2-羧基-6-內酯、3-甲基丙烯醯氧基丙基三乙氧基矽烷、縮水甘油基甲基丙烯酸酯、2-苯基乙基甲基丙烯酸酯、羥基苯基甲基丙烯酸酯及溴苯基甲基丙烯酸酯等。
丙烯醯胺化合物例如有丙烯醯胺、N-甲基丙烯醯胺、
N-乙基丙烯醯胺、N-苄基丙烯醯胺、N-苯基丙烯醯胺、N,N-二甲基丙烯醯胺及N-蒽基丙烯醯胺等。
甲基丙烯醯胺化合物例如有甲基丙烯醯胺、N-甲基甲基丙烯醯胺、N-乙基甲基丙烯醯胺、N-苄基甲基丙烯醯胺、N-苯基甲基丙烯醯胺、N,N-二甲基甲基丙烯醯胺及N-蒽基甲基丙烯醯胺等。
乙烯基化合物例如有乙烯醇、2-羥基乙基乙烯醚、甲基乙烯醚、乙基乙烯醚、苄基乙烯醚、乙烯基乙酸、乙烯基三甲氧基矽烷、2-氯乙基乙烯醚、2-甲氧基乙基乙烯醚、乙烯基萘及乙烯基蒽等。
苯乙烯化合物例如有苯乙烯、羥基苯乙烯、氯苯乙烯、溴苯乙烯、甲氧基苯乙烯、氰基苯乙烯及乙醯基苯乙烯等。
馬來醯亞胺化合物例如有馬來醯亞胺、N-甲基馬來醯亞胺、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺及N-羥基乙基馬來醯亞胺等。
聚合物使用縮聚合聚合物時,這種聚合物例如有甘醇化合物與二羧酸化合物之縮聚合聚合物。甘醇化合物例如有二乙二醇、己二醇、丁二醇等。二羧酸化合物例如有琥珀酸、己二酸、對苯二甲酸、馬來酸酐等。又,例如有聚均苯四甲醯亞胺、聚(p-伸苯基對苯二甲醯胺)、聚對苯二甲酸丁二醇酯、聚對苯二甲酸乙二醇酯等聚酯、聚醯胺、聚醯亞胺。
有機聚合物化合物含有羥基時,此羥基可與聚有機矽
氧烷形成交聯反應。
有機聚合物化合物可使用重量平均分子量例如1000~1000000,或3000~300000,或5000~200000,或10000~100000之聚合物化合物。
有機聚合物可僅使用一種,或可組合二種以上使用。
使用有機聚合物化合物時,相對於縮合物(聚有機矽氧烷)100質量份時,其比率例如1~200質量份,或5~100質量份,或10~50質量份,或20~30質量份。
本發明之光阻下層膜形成組成物可含有酸產生劑。
酸產生劑例如有熱酸產生劑或光酸產生劑。
光酸產生劑係光阻曝光時產生酸。因此可調整下層膜之酸性度。此乃是使下層膜之酸性度配合上層之光阻之酸性度的一種方法。又藉由調整下層膜之酸性度,可調製形成於上層之光阻的圖型形狀。
本發明之光阻下層膜形成組成物中所含有的光酸產生劑,例如有鎓鹽化合物、磺醯亞胺化合物及二磺醯基重氮甲烷化合物等。
鎓鹽化合物例如有二苯基錪六氟磷酸鹽、二苯基錪三氟甲磺酸鹽、二苯基錪九氟正丁烷磺酸鹽、二苯基錪全氟正辛烷磺酸鹽、二苯基錪樟腦磺酸鹽、雙(4-第三丁苯基)錪樟腦磺酸鹽及雙(4-第三丁苯基)錪三氟甲磺酸鹽等之錪鹽化合物及三苯基鋶六氟銻酸鹽、三苯基鋶九氟正丁磺酸鹽、三苯基鋶樟腦磺酸鹽及三苯基鋶三氟甲磺酸鹽等之鋶鹽化合物等。
磺醯亞胺化物例如有N-(三氟甲磺醯氧基)琥珀醯亞胺、N-(九氟正丁磺醯氧基)琥珀醯亞胺、N-(樟腦磺醯氧基)琥珀醯亞胺及N-(三氟甲磺醯氧基)萘二甲醯亞胺等。
二磺醯基重氮甲烷化合物例如有雙(三氟甲基磺醯基)重氮甲烷、雙(環己基磺醯基)重氮甲烷、雙(苯基磺醯基)重氮甲烷、雙(對-甲苯磺醯基)重氮甲烷、雙(2,4-二甲基苯磺醯基)重氮甲烷及甲基磺醯基-對-甲苯磺醯基重氮甲烷等。
光酸產生劑可僅使用1種或組合2種以上使用。
使用光酸產生劑時,其比例係相對於上述縮合物(聚有機矽氧烷)100質量份,使用0.01~5質量份,或0.1~3質量份,或0.5~1質量份。
界面活性劑可有效抑制將本發明之微影用光阻下層膜形成組成物塗佈於基板時產生針孔及擴張等。
本發明之光阻下層膜形成組成物所含的表面活性劑,例如有聚環氧乙烷月桂醚、聚環氧乙烷硬脂醚、聚環氧乙烷十六烷醚、聚環氧乙烷油醚等聚環氧乙烷烷醚類、聚環氧乙烷辛基酚醚、聚環氧乙烷壬基酚醚等聚環氧乙烷烷基烯丙醚類、聚環氧乙烷.聚環氧丙烷嵌段共聚物類、山梨糖醇酐單月桂酸酯、山梨糖醇酐單棕櫚酸酯、山梨糖醇酐單硬脂酸酯、山梨糖醇酐單油酸酯、山梨糖醇酐三油酸酯、山梨糖醇酐三硬脂酸酯等山梨糖醇酐脂肪酸酯類、聚環氧乙烷山梨糖醇酐單月桂酸酯、聚環氧乙烷山梨糖醇酐單
棕櫚酸酯、聚環氧乙烷山梨糖醇酐單硬脂酸酯、聚環氧乙烷山梨糖醇酐三油酸酯、聚環氧乙烷山梨糖醇酐三硬脂酸酯等聚環氧乙烷山梨糖醇酐脂肪酸酯類等非離子系界面活性劑、商品名EFtop EF301、EF303、EF352(TOHKEM PRODUCTS(股)製)、商品名Megafac F171、F173、R-08、R-30(大日本油墨化學工業(股)製)、Fluorad FC430、FC431(住友3M(股)製)、商品名Asahiguad AG710、Suflon S-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(股)製)等氟系界面活性劑及有機矽氧烷聚合物KP341(信越化學工業(股)製)等。此等界面活性劑可單獨使用或組合二種以上使用。使用界面活性劑時,其比率係相對於縮合物(聚有機矽氧烷)100質量份,使用0.0001~5質量份或0.001~1質量份或0.01~0.5質量份。
又,本發明之光阻下層膜形成組成物可添加流變調整劑及接著補助劑等。流變調整劑可有效提升下層膜形成組成物之流動性。接著輔助劑可有效提升半導體基板或光阻與下層膜之密著性。
使用於本發明之光阻下層膜形成組成物的溶劑,只要是可溶解前述固體成分的溶劑即可,並無特別限定使用。這種溶劑例如有甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、丙二醇、丙二醇單甲醚、丙二醇單乙醚、甲基異丁基卡必醇、丙二醇單丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單丁醚乙酸酯、甲
苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯、丙酮酸甲酯、丙酮酸乙酯、乙二醇單甲醚、乙二醇單乙基醚、乙二醇單丙醚、乙二醇單丁醚、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丙醚、二乙二醇二丁醚、丙二醇單甲醚、丙二醇二甲醚、丙二醇二乙醚、丙二醇二丙醚、丙二醇二丁醚、乳酸乙酯、乳酸丙酯、乳酸異丙酯、乳酸丁酯、乳酸異丁酯、甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸異丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊酯、甲酸異戊酯、乙酸甲酯、乙酸乙酯、乙酸戊酯、乙酸異戊酯、乙酸己酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、丙酸丁酯、丙酸異丁酯、丁酸甲酯、丁酸乙酯、丁酸丙酯、丁酸異丙酯、丁酸丁酯、丁酸異丁酯、羥基乙酸乙酯、2-羥基-2-甲基丙酸乙酯、3-甲氧基-2-甲基丙酸甲酯、2-羥基-3-甲基丁酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲氧基丙基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基丙酸酯、3-甲基-3-甲氧基丁基丁酸酯、乙醯乙酸甲酯、甲苯、二甲苯、甲基乙基酮、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、環己
酮、N,N-二甲基甲醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮及γ-丁內酯等。此等溶劑可單獨或組合二種以上使用。
以下說明本發明之光阻下層膜形成組成物之使用。
藉由旋塗機、塗佈器等適當塗佈方法,將本發明之光阻下層膜形成組成物塗佈於製造半導體裝置用的基板(例如矽晶圓基板、矽/二氧化矽被覆基板、氮化矽基板、玻璃基板、ITO基板、聚醯亞胺基板及低電容率材料(low-k材料)被覆基板等)上,然後藉由燒成形成光阻下層膜。
燒成條件可自燒成溫度80℃~250℃、燒成時間0.3~60分鐘中適當選擇。較佳為燒成溫度150℃~250℃、燒成時間0.5~2分鐘。所形成的下層膜之膜厚,例如10~1000nm,或20~500nm,或50~300nm,或100~200nm。
其次,於該光阻下層膜上形成例如光阻的層。形成光阻之層時係藉由已知方法,即將光阻組成物溶液塗佈於下層膜上及進行燒成。光阻之膜厚例如50~10000nm,或100~2000nm,或200~1000nm。
本發明係在基板上形成有機下層膜後,此上形成本發明之光阻下層膜,可再於其上被覆光阻。藉此光阻之圖型寬變狹窄,為了防止倒塌,即使被覆薄的光阻時,也可藉由選擇適當的蝕刻氣體,對基板加工。例如以對於光阻為充分快速之蝕刻速度的氟系氣體作為蝕刻氣體,可對本發明之光阻下層膜進行加工,又,以對於本發明之光阻下層膜為充分快速之蝕刻速度的氧系氣體作為蝕刻氣體,可對
有機下層膜進行加工,再以對於有機下層膜為充分快速之蝕刻速度的氟系氣體作為蝕刻氣體,可對基板進行加工。
形成於本發明之光阻下層膜上之光阻,只要是可感應曝光使用的光者,即無特別限定。可使用負型光阻及正型光阻。例如有由酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所構成之正型光阻、由具有藉由酸分解提升鹼溶解速度之基團的黏結劑與光酸產生劑所構成之化學加強型光阻及由藉由酸分解提升光阻之鹼溶解速度的低分子化合物、鹼可溶性黏結劑及光酸產生劑所構成之化學加強型光阻,及由具有藉由酸分解提升鹼溶解速度之基團之黏結劑、藉由酸分解提升光阻之鹼溶解速度的低分子化合物及光酸產生劑所構成之化學加強型光阻等。例如有Shipley公司製商品名APEX-E、住友化學工業(股)製商品名PAR710,及信越化學工業(股)製商品名SEPR430等。此外,例如有記載於Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)、Proc.SPIE,Vol.3999,365-374(2000)之含氟原子聚合物系光阻。
其次,通過所定光罩進行曝光。曝光時可使用KrF準分子雷射(波長248nm)、ArF準分子雷射(波長193nm)及F2準分子雷射(波長157nm)等。曝光後,必要時也可進行曝光後加熱(post exposure bake)。曝光後加熱可適當選擇加熱溫度70℃~150℃,加熱時間0.3~10分鐘的條件下進行。
又,本發明可使用電子線微影蝕刻用光阻取代光阻。
電子線光阻可使用負型及正型中任一者。例如有由酸產生劑與具有藉由酸分解改變鹼溶解速度之基團的黏結劑所構成之化學加強型光阻、由鹼可溶性黏結劑、酸產生劑及藉由酸分解改變光阻之鹼溶解速度之低分子化合物所構成的化學加強型光阻、由酸產生劑、具有藉由酸分解改變鹼溶解速度之基團之黏結劑及藉由酸分解改變光阻之鹼溶解速度的低分子化合物所構成的化學加強型光阻、由具有藉由電子線分解改變鹼溶解速度之基團之黏結劑所構成的非化學加強型光阻,由具有藉由電子線切斷、改變鹼溶解速度之部位的黏結劑所構成的非化學加強型光阻等。使用此等電子線光阻時,與照射源為電子線,使用光阻時同樣,可形成光阻圖型。
其次,藉由顯像液進行顯像。藉此例如使用正型光阻時,曝光部分之光阻被去除,形成光阻圖型。
顯像液例如有氫氧化鉀、氫氧化鈉等鹼金屬氧化物的水溶液、氫氧化四甲銨、氫氧化四乙銨、膽鹼等氫氧化四級銨的水溶液、乙醇胺、丙胺、乙二胺等胺水溶液等的鹼性水溶液。又此等顯像液中可添加界面活性劑等。顯像條件可適當選自溫度5~50℃、時間10~600秒。
接著,如此形成之光阻(上層)的圖型作為保護膜,除去本發明之光阻下層膜(中間層),再以由圖型化後的光阻及本發明之光阻下層膜(中間層)所形成的膜作為保護膜,除去有機下層膜(下層)。最後,以圖型化後之本發明的光阻下層膜(中間層)及有機下層膜(下層)作為
保護膜,對半導體基板進行加工。
首先,藉由乾蝕刻除去已被去除光阻之部分的本發明之光阻下層膜(中間層),使半導體基板露出。本發明之光阻下層膜的乾蝕刻時,可使用四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷、一氧化碳、氬、氧、氮、六氟化硫、二氟甲烷、三氟化氮及三氟化氯、氯、三氯硼烷及二氯硼烷等氣體。光阻下層膜之乾蝕刻,較佳為使用鹵系氣體。藉由鹵系氣體之乾蝕刻,基本上不易去除由有機物質形成之光阻。然而,含有較多矽原子之本發明的光阻下層膜可藉由鹵系氣體快速除去。因此可抑制光阻下層膜之乾蝕刻所伴隨之光阻膜厚之減少。結果,光阻可使用薄膜狀。光阻下層膜之乾蝕刻,較佳為藉由氟系氣體,而氟系氣體例如有四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷,及二氟甲烷(CH2F2)等。
其後,以由圖型化後之光阻及本發明之光阻下層膜所形成的膜作為保護膜,除去有機下層膜。有機下層膜(下層)較佳為使用氧系氣體進行乾蝕刻。因為含有較多矽原子之本發明的光阻下層膜不易使用氧系氣體進行乾蝕刻被除去的緣故。
最後,對半導體基板進行加工。半導體基板加工較佳為使用氟系氣體進行乾蝕刻。
氟系氣體例如有四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷,及二氟甲烷(
CH2F2)等。
又,本發明之光阻下層膜的上層,於形成光阻前可形成有機系防反射膜。此時所使用的防反射膜組成物並無特別限制,可由目前為止微影製程所慣用者中任意選用,又慣用的方法,例如使用旋塗機、塗佈器之塗佈及燒成,可形成防反射膜。
又,塗佈有本發明之光阻下層膜形成組成物的基板,可為其表面上具有以CVD法等形成的有機系或無機系防反射膜者,且其上可形成本發明的下層膜。
由本發明之光阻下層膜形成組成物形成的光阻下層膜,有時因微影製程所使用之光的波長,對該光具有吸收性。此時,可作為具有防止由基板反射光之效果的防反射膜的功能。另外,本發明之下層膜也可作為防止基板與光阻之相互作用的層、具有防止光阻所使用的材料或對光阻曝光時所生成之物質對基板不良作用之功能的層、具有防止加熱燒成時由基板生成的物質擴散至上層光阻之功能的層、及減少因半導體基板介電體層造成光阻層之中毒效果用之阻擋層等使用。
又,由本發明之光阻下層膜形成組成物形成的光阻下層膜可作為適用於形成有雙金屬嵌入製程所使用的通路孔的基板,可以無間隙填充孔的埋入材使用。又,也可作為使具有凹凸之半導體基板的表面平坦化的平坦化材使用。
以下藉由實施例更具體說明本發明,但是本發明不限於此等。
關於所得之化合物係藉由1H-NMR測定,進行確認。
試料管:5mm、溶劑:重氫化氯仿、測定溫度:室溫、脈衝間隔:5秒、累積次數:32次、基準試料:四甲基矽烷(TMS)。
在附磁力攪拌器之200ml之四口燒瓶中加入烯丙基溴7.70g、乙醯基丙酮19.0g(相對於烯丙基溴為3當量)、碳酸鉀17.4g(相對於烯丙基溴為2當量)、丙酮61g,以60℃迴流9小時下進行攪拌。冷卻至室溫後,減壓餾除丙酮,使用乙酸乙酯60g稀釋。添加1N鹽酸直到成為pH3為止,有機相以純水50g洗2次。有機相經濃縮.乾燥,得到中間體1(7.3g)(收率為82%)。
1H-NMR(400MHz):酮體;2.20ppm(s、6H)、2.61ppm(m、2H)、3.73ppm(t、1H)、5.05~5.12ppm(m、2H)、5.68~5.77ppm(m、1H)、烯醇體;2.11ppm(s、6H)、2.99ppm(m、2H)、5.05~5.12ppm(m、2H)、5.79~5.96ppm(m、1H)。酮體:烯醇之莫耳比=71:29。
其次,於附磁力攪拌器之100ml之四口燒瓶中加入中間體1(6.93g)、karstedt’s觸媒(白金(0)-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之0.1M/l的二甲苯溶液
)490μl、甲苯42g,然後將三乙氧基矽烷10.8ml(相對於反應中間體1為1.2當量)以10分鐘滴加。以室溫攪拌1日後,所得之粗產物以減壓蒸餾進行純化,得到目的物之化合物1(10.23g)(收率為68%)。
1H-NMR(400MHz):酮體;0.64ppm(t、2H)、1.23ppm(t、9H)、1.37ppm(quint、2H)、1.89ppm(q、2H)、2.19ppm(s、6H)、3.63ppm(t、1H)、3.81ppm(q、6H)、烯醇體;0.68ppm(t、2H)、1.25ppm(t、9H)、1.52ppm(quint、2H)、2.14ppm(s、6H)、2.26ppm(t、2H)、3.80ppm(q、6H)。酮體:烯醇之莫耳比=72:28。
計算化合物1之pKa得到10.57。
化合物1之反應圖解如下述所示。
在附磁力攪拌器之200ml之四口燒瓶中加入碳酸鉀9.38g(相對於三氟乙醯基乙酸乙酯為0.5當量)、丙酮30g,在室溫下攪拌。然後將烯丙基溴8.21g(相對於三氟乙醯基乙酸乙酯為0.5當量)、三氟乙醯基乙酸乙酯25.00g溶解於丙酮20g中的溶液滴下。其後,以60℃迴流4小時進行攪拌。冷卻至室溫後,將反應液以乙酸乙酯
200g、純水50g稀釋,添加1N鹽酸直到成為pH3為止。除去水相後,再將有機相以飽和食塩水50g洗1次。有機相經濃縮乾燥,所得之粗生成物以減壓蒸餾進行純化得到中間體2(10.0g)(收率為66%)。
1H-NMR(400MHz)酮體;1.27ppm(t、3H)、2.71ppm(t、2H)、3.94ppm(t、1H)、4.20ppm(q、2H)、5.06~5.17ppm(m、2H)、5.68~5.80ppm(m、1H)、烯醇體;1.32ppm(t、3H)、3.00ppm(dd、2H)、4.27ppm(q、2H)、5.06~5.17ppm(m、2H)、5.68~5.80ppm(m、1H)、酮體:烯醇之莫耳比=58:42。
其次,於附磁力攪拌器之200ml之四口燒瓶中加入中間體2(10.00g)、karstedt’s觸媒(白金(0)-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之0.25M/l的二甲苯溶液)1120μl、甲苯60g,將三乙氧基矽烷9.8ml(相對於反應中間體2為1.2當量)以10分鐘滴加。以室溫攪拌4小時後,反應液經濃縮乾燥,所得之粗產物以減壓蒸餾進行2次純化,得到化合物2(4.33g)(收率為25%)。
1H-NMR(400MHz)inCDCl3:酮體;0.65ppm(t、2H)、1.27ppm(t、9H)、1.35ppm(t、2H)、1.40~1.54ppm(m、2H)、2.33ppm(t、1H)、3.82ppm(q、6H)、4.31ppm(q、2H)、烯醇體;0.65ppm(t、2H)、1.22ppm(t、9H)、1.45ppm(q、2H)、2.00ppm(q、2H)、3.80ppm(q、6H)、4.21ppm(q、2H)、酮體:烯醇之莫耳比=20:80。
計算化合物2之pKa得到8.84。
化合物2之反應圖解如下述所示。
在附磁力攪拌器之200ml之四口燒瓶中加入烯丙基丙二酸二乙酯15.00g、karstedt’s觸媒(白金(0)-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之0.25M/l的二甲苯溶液)1870μl、甲苯90g,將三乙氧基矽烷13.7ml(相對於烯丙基丙二酸二乙酯為1.1當量)以10分鐘滴加。以室溫攪拌5小時後,反應液經濃縮乾燥,所得之粗產物以減壓蒸餾進行純化,得到化合物3(16.68g)(收率為61%)。
1H-NMR(400MHz)inCDCl3:酮體;0.66ppm(t、2H)、1.22ppm(t、9H)、1.27ppm(t、6H)、1.42~1.50ppm(m、2H)、1.93ppm(q、2H)、3.34ppm(t、1H)、3.81ppm(q、6H)、4.20ppm(q、4H)、酮體:烯醇之莫耳比=100:0。
計算化合物3之pKa得到12.97。
化合物3之反應圖解如下述所示。
在附磁力攪拌器之200ml之四口燒瓶中加入烯丙基丙二酸二第三丁酯19.2g、karstedt’s觸媒(白金(0)-1,3-二乙烯基-1,1,3,3-四甲基二矽氧烷錯合物之0.25M/l的二甲苯溶液)1870μl、甲苯90g,將三乙氧基矽烷13.7ml(相對於烯丙基丙二酸二第三丁酯為1.1當量)以10分鐘滴加。以室溫攪拌5小時後,反應液經濃縮乾燥,所得之粗產物以減壓蒸餾進行純化,得到化合物4(17.01g)(收率為54%)。
1H-NMR(400MHz)inCDCl3:酮體;0.66ppm(t、2H)、1.42~1.50ppm(m、20H)、1.93ppm(q、2H)、3.33ppm(t、1H)、3.82ppm(q、6H)、4.21ppm(q、4H)、酮體:烯醇之莫耳比=100:0。
計算化合物4之pKa得到12.90。又,將化合物4以0.01M/l之稀鹽酸水溶液水解轉換成二羧酸後的衍生物的pKa為5.78。
化合物4之反應圖解如下述所示。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.57g(全矽烷中為20莫耳%)、丙酮30.99g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-1))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(2)1.94g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧
基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.57g(全矽烷中為20莫耳%)、丙酮31.62g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-2))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1500。
將化合物(3)1.94g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.57g(全矽烷中為20莫耳%)、丙酮31.62g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-3
))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-甲氧基苄基)三甲氧基矽烷0.36g(全矽烷中為1.5莫耳%)、丙酮31.14g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-4))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1500。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-乙氧基苯基)
三甲氧基矽烷0.36g(全矽烷中為1.5莫耳%)丙酮31.14g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-5))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1500。
化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-乙氧基乙氧基苯基)三甲氧基矽烷0.43g(全矽烷中為1.5莫耳%)丙酮31.24g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當
於式(5-6))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-乙氧基乙氧基苄基)三乙氧基矽烷0.51g(全矽烷中為1.5莫耳%)丙酮31.36g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-7))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、3-(三乙氧基矽烷基丙基)二烯丙基三聚異氰酸酯2.07g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.56g(全矽烷中為20莫
耳%)、丙酮32.61g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯22.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-8))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、3-(三乙氧基矽烷基丙基)二烯丙基三聚異氰酸酯2.07g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-甲氧基苄基)三甲氧基矽烷0.36g(全矽烷中為1.5莫耳%)、丙酮32.75g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯22.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-9))。所得之聚合物藉
由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、3-(三乙氧基矽烷基丙基)二烯丙基三聚異氰酸酯2.07g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-乙氧基苯基)三甲氧基矽烷0.36g(全矽烷中為1.5莫耳%)、丙酮32.75g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯22.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-10))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、3-(三乙氧基矽烷基丙基)二烯丙基三聚異氰酸酯2.07g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-乙氧基乙氧基苯基)三甲氧基矽烷0.43g(
全矽烷中為1.5莫耳%)、丙酮32.85g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯22.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(5-11))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(1)1.52g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、3-(三乙氧基矽烷基丙基)二烯丙基三聚異氰酸酯2.07g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.30g(全矽烷中為18.5莫耳%)、(4-乙氧基乙氧基苄基)三甲氧基矽烷0.51g(全矽烷中為1.5莫耳%)、丙酮32.98g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯22.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到
15%之水解縮合物溶液(相當於式(5-12))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1500。
將四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷4.46g(全矽烷中為25莫耳%)、丙酮30.05g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.68g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯20.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(6-1))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw1600。
將化合物(4)2.10g(全矽烷中為5莫耳%)、四乙氧基矽烷14.58g(全矽烷中為70莫耳%)、苯基三甲氧基矽烷0.99g(全矽烷中為5莫耳%)、甲基三乙氧基矽烷3.57g(全矽烷中為20莫耳%)、丙酮31.86g加入100mL之燒瓶中,使溶解所得之混合溶液以磁力攪拌器攪拌同時加溫、迴流。其次,將0.01M之鹽酸水溶液6.67g添加於混合溶液中。反應240分鐘後,所得之反應溶液冷卻至室溫。然後,反應溶液中添加丙二醇單甲醚乙酸酯21.00g,減壓餾除反應副產物之乙醇、水、鹽酸,得到水解縮合物溶液。其後,在水解縮合物溶液中添加丙二醇二乙醚,最後得到15%之水解縮合物溶液(相當於式(6-2))。所得之聚合物藉由GPC之重量平均分子量係以聚苯乙烯換算為Mw2100。
將前述合成例1~12及比較合成例1~2所得之含矽、酸、硬化觸媒、添加劑、溶劑、水以如表1所示的比例進行混合,藉由0.1μm之氟樹脂製之過濾器過濾,分別調製
光阻下層膜形成用組成物的溶液。
表1中,馬來酸係以MA表示,苄基三乙基氯化銨係以BTEAC表示,N-(3-三乙氧基矽烷基丙基)-4,5-二氫咪唑係以IMIDTEOS表示,馬來酸單三苯基鋶係以TPSMA表示,乙醯基丙酮係以AcAc表示,三氟乙醯基乙酸乙酯係以TfAcEt表示,丙二酸二乙酯係以MADE表示,丙二醇單甲醚乙酸酯係以PGMEA表示,丙二醇單甲醚係以PGME表示,丙二醇單乙醚係以PGEE表示。水係使用超純水。各添加量係以質量份表示。聚合物之添加量並非聚合物溶液的質量而是聚合物的質量。
使用旋轉塗佈法將光阻下層膜形成組成物塗佈於矽晶圓上,在140℃之加熱板上進行燒成1分鐘,形成光阻下層膜。然後,於上塗光阻組成物之溶劑用的丙二醇單甲醚乙酸酯中浸漬1分鐘,浸漬前後之光阻下層膜之膜厚的變化在1nm以下時,判斷為「良好」。表2中以「○」表示。
使用旋轉器將光阻下層膜形成組成物塗佈於矽晶圓上。在加熱板上以240℃加熱1分鐘,形成光阻下層膜(膜厚為0.09μm)。然後,對於此等光阻下層膜,使用分光橢圓對稱計(J.A.Woollam公司製,VUV-VASE VU-302)測定波長193nm下之折射率(n值)及光學吸光係數(k值,或稱衰減係數)。結果如表3所示。
測定乾蝕刻速度用之蝕刻器及蝕刻用氣體係使用如下述者。
蝕刻器係使用ES401(日本科學公司製),以蝕刻氣體四氟化碳(CF4)進行蝕刻。
蝕刻器係使用蝕刻器RIE-10NR(Samco公司製),以蝕刻氣體氧氣(O2)進行蝕刻。
使用旋轉器將實施例1~14及比較例1~5所調製之光阻下層膜形成組成物的溶液塗佈於矽晶圓上。在加熱板以240℃加熱1分鐘,形成光阻下層膜,使用各蝕刻氣體測定蝕刻速度。光阻下層膜的膜厚0.20μm,使用蝕刻氣體四氟化碳(CF4)測定蝕刻速度,光阻下層膜的膜厚0.04μm,使用蝕刻氣體氧氣(O2)測定蝕刻速度。
又,同樣地使用旋轉器將光阻溶液(Shipley公司製,商品名為UV113)塗佈在矽晶圓上分別形成0.20μm與0.04μm的光阻膜。蝕刻氣體使用CF4氣體及O2氣體測定乾蝕刻速度。比較光阻下層膜與光阻膜之乾蝕刻速度。結果如表4所示。速度比係(光阻下層膜)/(光阻)之乾蝕刻速度比。
200mL之燒瓶中添加苊烯16.5g、4-羥基苯乙烯1.5g、溶劑:1,2-二氯乙烷60g。添加聚合起始劑:三氟硼1g,昇溫至60℃後,反應24小時。此溶液中添加甲醇1L、水500g,進行再沈澱純化,將所得之白色固體過濾後,經乾燥得到白色聚合物11g。將下述所得之聚合物(相當於
)進行13C-NMR、1H-NMR及GPC測定,測得苊烯:4-羥基苯乙烯=86:14。Mw:6000、Mw/Mn=1.5。
在所得之聚合物(式(7-1))10g中添加四甲氧基甲基甘脲(三井SCITECH(股)製、商品名powdering1174)1.0g、交聯觸媒:對甲苯磺酸0.01g、界面活性劑:Magafac R-30(大日本油墨化學(股)製、商品名)0.03g,再溶解於丙二醇單甲醚乙酸酯101.57g、丙二醇單甲醚25.39g中。然後,使用孔徑0.10μm之聚乙烯製微孔過濾器過濾,再使用孔徑0.05μm之聚乙烯製微孔過濾器過濾調製多層膜之微影製程用之光阻下層膜形成組成物的溶液。
將含有上述聚合物(式(7-1))之有機下層膜(A層)形成組成物塗佈於矽晶圓上,在加熱板上以240℃加熱1分鐘,得到膜厚250nm之有機下層膜(A層)。其上分別塗佈實施例1~實施例14及比較例1~比較例5所得之含Si光阻下層膜(B層)組成物,在加熱板上以240℃加
熱1分鐘,得到膜厚40nm之含Si光阻下層膜(B層)。其上使用旋轉器塗佈市售光阻溶液(住友化學工業(股)製,商品名PAR855),在加熱板上以100℃加熱1分鐘,形成膜厚150nm之光阻膜(C層)。光阻的圖型化係使用ASML公司製液浸曝光機TWINSCAN XT:1900Gi掃描機(波長193nm、NA、σ:1.20、0.94/0.74(C-quad)液浸液:水)進行。目標為顯像後,光阻之線寬及該線間之寬為0.05μm,所謂線與間隙(稠密線),透過設定線條數形成15條的光罩進行曝光。然後,在加熱板上以105℃烘烤60秒鐘,冷卻後,以工業規格之60秒單槳(Paddle)式步驟,使用2.38%之四甲銨氫氧化物顯像液進行顯像。
將光阻下層膜形成組成物以23℃保存2個月,再度進行塗佈膜厚測定及微影評價。
以23℃保存2個月後之塗佈膜厚無變化時,以○表示,有變化時,顯示其變化量。
由本發明之具有二酮、烯醇、或酮酯結構之光阻下層膜形成組成物所得的光阻下層膜係因含有許多雜(Hetero)元素,因此對於光阻膜具有充分高的乾蝕刻速度。實施例1~14相對於比較例1時,可提高藉由氟系氣體之蝕刻速度,故可將本發明之光阻下層膜之上層的光阻圖型正確轉印
至本發明之光阻下層膜。
由實施例1~14之光阻下層膜形成組成物所得的光阻下層膜,相對於由比較例1之光阻下層膜形成組成物所得的光阻下層膜時,藉由氧氣體之蝕刻耐性相同,因此具有作為本發明之光阻下層膜之更下層的有機下層膜或基板進行加工時之硬光罩之充分高的功能者。
又,進行0.05μm之光阻圖型化時,實施例1、4、5與比較例2~5比較時,在聚合物中含有二酮、烯醇、或酮酯結構之實施例1、4、5係顯示良好的微影特性,而聚合物不含上述二酮、烯醇、或酮酯結構之比較例2~4則成為底腳(Footing)形狀,因此藉由導入於聚合物中,可抑制底腳形狀。又,各材料中,含有使矽烷醇安定化之二酮結構,因此安定性較高,但是為了形成良好的初期特性、一定期間後之微影特性時,在聚合物中含有二酮、烯醇、或酮酯結構之材料(實施例1~14)效果較佳。
而比較例5中,在聚合物中含有二酯結構,但是酯部位在溶膠凝膠水解條件下為酸不安定基(t-丁基),因此水解性有機矽烷之水解與縮合過程,即使使用0.01M/l之稀鹽酸水溶液,也會變成二羧酸,結果pKa降低。如此,溶膠凝膠反應中,產生脫保護反應,系內pH變化而提高酸性度,因此,光阻形狀顯示底切(under cut)形狀。又,因系內之pH變化,因此比較例5為安定性低者。
可作為形成作為硬光罩使用之光阻下層膜用之微影用光阻下層膜形成組成物使用。不會產生與光阻之互相混合,相較於光阻,具有較大的乾蝕刻速度之微影用光阻下層膜及可作為形成該下層膜用之光阻下層膜形成組成物使用。
Claims (12)
- 一種半導體裝置之製造方法,其特徵係含有以下步驟:將微影用光阻下層膜形成組成物塗佈於半導體基板上,經燒成形成光阻下層膜的步驟;在前述下層膜之上塗佈光阻膜形成組成物,形成光阻膜的步驟;使前述光阻膜曝光的步驟;曝光後,使該光阻膜顯像,得到圖型化之光阻膜的步驟;遵循該圖型化之光阻膜,蝕刻光阻下層膜得到圖型化之光阻下層膜的步驟;及遵循該圖型化之光阻膜與圖型化之光阻下層膜,對半導體基板進行加工的步驟,其中該微影用光阻下層膜形成組成物係含有作為矽烷之水解性有機矽烷、前述水解性有機矽烷之水解物、或前述水解性有機矽烷之水解縮合物,該水解性有機矽烷為含有下述式(1):【化1】〔(R1)aSi(R2)(3-a)〕b(R3) 式(1)[式中R3係式(2)、式(3)、或式(4):
- 如申請專利範圍第1項之製造方法,其中前述水解性有機矽烷為含有式(5):【化3】R1 aSi(R2)4-a 式(5)(式中R1分別獨立表示烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、烷氧基芳基、醯氧基芳基或氰基之有機基、或彼等之組合,且藉由Si-C鍵與矽原子鍵結的基團,R2分別獨立表示烷氧基、醯氧基、或鹵素原子,a係表示0~3之整數)表示之有機矽化合物及式(6):【化4】〔R1 cSi(R2)3-c〕2Yb 式(6)(式中,R1表示烷基,R2分別獨立表示烷氧基、醯氧基、或鹵素原子,Y表示伸烷基或伸芳基,b表示0或1之整數,c係表示0或1之整數)表示之有機矽化合物所成群中選出之至少1種的有機矽化合物與上述式(1)表 示之水解性有機矽烷之組合、前述有機矽化合物與上述式(1)表示之水解性有機矽烷之水解物及前述有機矽化合物與上述式(1)表示之水解性有機矽烷之水解縮合物所成群中選出之至少1種。
- 如申請專利範圍第1項之製造方法,其中含有上述式(1)表示之水解性有機矽烷之水解縮合物、或上述式(1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之水解縮合物作為聚合物。
- 如申請專利範圍第1項之製造方法,其中上述式(1)表示之水解性有機矽烷為具有8.00~20.00之pKa值者。
- 如申請專利範圍第1項之製造方法,其中該微影用光阻下層膜形成組成物係再含有酸作為水解觸媒。
- 如申請專利範圍第1項之製造方法,其中該微影用光阻下層膜形成組成物係再含有水。
- 一種半導體裝置之製造方法,其特徵係含有以下步驟:於半導體基板上形成有機下層膜的步驟;於其上塗佈微影用光阻下層膜形成組成物,經燒成形成光阻下層膜的步驟;在前述光阻下層膜之上塗佈光阻膜形成組成物,形成光阻膜的步驟;使前述光阻膜曝光的步驟;曝光後,使該光阻膜顯像,得到圖型化之光阻膜的步 驟;遵循該圖型化之光阻膜,蝕刻光阻下層膜得到圖型化之光阻下層膜的步驟;遵循該圖型化之光阻下層膜,蝕刻有機下層膜的步驟;及遵循該圖型化之有機下層膜,對半導體基板進行加工的步驟,其中該微影用光阻下層膜形成組成物係含有作為矽烷之水解性有機矽烷、前述水解性有機矽烷之水解物、或前述水解性有機矽烷之水解縮合物,該水解性有機矽烷為含有下述式(1):【化1】〔(R1)aSi(R2)(3-a)〕b(R3) 式(1)[式中R3係式(2)、式(3)、或式(4):
- 如申請專利範圍第7項之製造方法,其中前述水解性有機矽烷為含有式(5): 【化3】R1 aSi(R2)4-a 式(5)(式中R1分別獨立表示烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、氫硫基、烷氧基芳基、醯氧基芳基或氰基之有機基、或彼等之組合,且藉由Si-C鍵與矽原子鍵結的基團,R2分別獨立表示烷氧基、醯氧基、或鹵素原子,a係表示0~3之整數)表示之有機矽化合物及式(6):【化4】〔R1 cSi(R2)3-c〕2Yb 式(6)(式中,R1係表示烷基,R2分別獨立表示烷氧基、醯氧基、或鹵素原子,Y係表示伸烷基或伸芳基,b係表示0或1之整數,c係表示0或1之整數)表示之有機矽化合物所成群中選出之至少1種的有機矽化合物與上述式(1)表示之水解性有機矽烷之組合、前述有機矽化合物與上述式(1)表示之水解性有機矽烷之水解物及前述有機矽化合物與上述式(1)表示之水解性有機矽烷之水解縮合物所成群中選出之至少1種。
- 如申請專利範圍第7項之製造方法,其中含有上述式(1)表示之水解性有機矽烷之水解縮合物、或上述式 (1)表示之水解性有機矽烷與式(5)表示之有機矽化合物之水解縮合物作為聚合物。
- 如申請專利範圍第7項之製造方法,其中上述式(1)表示之水解性有機矽烷為具有8.00~20.00之pKa值者。
- 如申請專利範圍第7項之製造方法,其中該微影用光阻下層膜形成組成物係再含有酸作為水解觸媒。
- 如申請專利範圍第7項之製造方法,其中該微影用光阻下層膜形成組成物係再含有水。
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KR101570138B1 (ko) * | 2007-09-11 | 2015-11-18 | 닛산 가가쿠 고교 가부시키 가이샤 | 질소함유실릴기를 포함하는 폴리머를 함유하는 레지스트 하층막 형성 조성물 |
KR101524712B1 (ko) * | 2007-11-30 | 2015-06-01 | 닛산 가가쿠 고교 가부시키 가이샤 | 블록화 이소시아네이트기를 갖는 실리콘 함유 레지스트 하층막 형성 조성물 |
JP5360416B2 (ja) * | 2008-01-11 | 2013-12-04 | 日産化学工業株式会社 | ウレア基を有するシリコン含有レジスト下層膜形成組成物 |
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2012
- 2012-01-24 CN CN201280006068.XA patent/CN103339569B/zh active Active
- 2012-01-24 US US13/981,142 patent/US9291900B2/en active Active
- 2012-01-24 EP EP12739813.9A patent/EP2669737A1/en not_active Withdrawn
- 2012-01-24 KR KR1020137017718A patent/KR101921513B1/ko active IP Right Grant
- 2012-01-24 JP JP2012554798A patent/JP5818026B2/ja active Active
- 2012-01-24 WO PCT/JP2012/051419 patent/WO2012102261A1/ja active Application Filing
- 2012-01-24 SG SG2013056361A patent/SG192113A1/en unknown
- 2012-01-30 TW TW101102878A patent/TWI596436B/zh active
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JP2000039292A (ja) * | 1998-07-22 | 2000-02-08 | Showa Alum Corp | アルミニウム系金属製熱交換器の防錆・防食表面処理方法 |
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Publication number | Publication date |
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US20130302991A1 (en) | 2013-11-14 |
KR101921513B1 (ko) | 2018-11-26 |
JP5818026B2 (ja) | 2015-11-18 |
EP2669737A1 (en) | 2013-12-04 |
SG192113A1 (en) | 2013-08-30 |
JPWO2012102261A1 (ja) | 2014-06-30 |
WO2012102261A1 (ja) | 2012-08-02 |
KR20140006822A (ko) | 2014-01-16 |
CN103339569A (zh) | 2013-10-02 |
TW201245888A (en) | 2012-11-16 |
US9291900B2 (en) | 2016-03-22 |
CN103339569B (zh) | 2018-12-07 |
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