TWI618985B - 具有碸構造之含矽阻劑底層膜形成組成物 - Google Patents
具有碸構造之含矽阻劑底層膜形成組成物 Download PDFInfo
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- TWI618985B TWI618985B TW101128962A TW101128962A TWI618985B TW I618985 B TWI618985 B TW I618985B TW 101128962 A TW101128962 A TW 101128962A TW 101128962 A TW101128962 A TW 101128962A TW I618985 B TWI618985 B TW I618985B
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- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- AZADLAPXFZPRFJ-UHFFFAOYSA-N sulfanylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCS AZADLAPXFZPRFJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DVUVKWLUHXXIHK-UHFFFAOYSA-N tetraazanium;tetrahydroxide Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[OH-].[OH-].[OH-].[OH-] DVUVKWLUHXXIHK-UHFFFAOYSA-N 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical class C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 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
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- XUECSRVFRKTFKJ-UHFFFAOYSA-N tritylhydrazine Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(NN)C1=CC=CC=C1 XUECSRVFRKTFKJ-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
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Abstract
提供微影術用阻劑底層膜形成組成物。
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,該矽烷為下述式(1):【化1】〔(R 1 ) a Si(R 2 ) (3-a) 〕 b (R 3 ) 式(1)
〔式(1)中,R3為含有磺醯基與吸光基,且以Si-C鍵結與Si原子鍵結的有機基,R1為烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、或彼等之組合,且以Si-C鍵結與Si原子鍵結的有機基。R2為烷氧基、醯基氧基、或鹵素基。a為0~2之整數,b為1~3之整數。〕。
Description
本發明為新穎矽烷化合物。而且係關於在半導體裝置的製造所使用的基板與阻劑(例如光阻、電子線阻劑、EUV阻劑)之間形成底層膜用之組成物。詳細係關於在半導體裝置製造的微影術步驟中,用以形成光阻的底層所使用的底層膜之微影術用阻劑底層膜形成組成物。又,關於使用該底層膜形成組成物之阻劑圖型的形成方法。
以往半導體裝置的製造中,進行使用光阻的微影術之微細加工。前述微細加工係在矽晶圓等之半導體基板上形成光阻的薄膜,於其上透過描繪有半導體裝置的圖型之遮罩圖型,照射紫外線等之活性光線,並顯影,以得到的光阻圖型作為保護膜進行基板蝕刻處理,而在基板表面形成對應前述圖型之微細凹凸的加工法。然而,近年伴隨半導體裝置的高積體度化,使用的活性光線亦有由KrF準分子雷射(248nm)朝向ArF準分子雷射(193nm)、EUV光(13.5nm)短波長化之傾向。伴隨此,活性光線來自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底層膜,使用已知作為含矽等之金屬元素的硬遮罩之膜(例如專利文獻1作參考)。此時,因阻劑與硬遮罩,其構成成分有大差異,彼等以乾蝕刻除去的速度極依賴乾蝕刻所使用的氣體種
類。接著,藉由適當選擇氣體種類,可不使光阻的膜厚大幅減少而使硬遮罩以乾蝕刻除去。如此,近年半導體裝置的製造中,為了達成以防反射效果為首之種種效果,開始在半導體基板與光阻間配置阻劑底層膜。而雖然一直探討阻劑底層膜用之組成物,但因其要求之特性的多樣性等,而期待阻劑底層膜用新穎材料之開發。
又,由別的觀點,亦有將基板表面改質之方法。例如使用具有磺醯基之矽烷耦合劑將曝光後之表面改變為親水性之方法(專利文獻2作參考)。
〔專利文獻1〕國際公開WO2011/033965號文獻
〔專利文獻2〕日本特開2005-112732號公報
本發明之目的在於提供可利用矩形阻劑圖型進行微細基板加工、可用於半導體裝置之製造的微影術用阻劑底層膜形成組成物。詳細係提供形成可用作為硬遮罩的阻劑底層膜用之微影術用阻劑底層膜形成組成物。又,提供形成可用作為防反射膜的阻劑底層膜用之微影術用阻劑底層膜形成組成物。又,提供不與阻劑產生互混,具有比阻劑大的乾蝕刻速度之微影術用阻劑底層膜及形成該底層膜用之阻劑底層膜形成組成物。
本發明之第1觀點為,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,且該水解性有機矽烷為下述式(1):[化1]〔(R 1 ) a Si(R 2 ) (3-a) 〕 b (R 3 ) 式(1)
〔式(1)中,R3為含有磺醯基與吸光基,且以Si-C鍵結與Si原子鍵結的有機基,R1為烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、或彼等之組合,且以Si-C鍵結與Si原子鍵結的有機基。R2為烷氧基、醯基氧基、或鹵素基。a為0~2之整數,b為1~3之整數。〕所表示的化合物之微影術用阻劑底層膜形成組成物、第2觀點為,上述式(1)之R3為下述式(2):
〔式(2)中,R4、Ar1、R5、Ar2、及R6之基中1個~3個的基為以Si-C鍵結與Si原子鍵結者,R4為可具有
硫鍵或醚鍵的1價~4價之烴基,R5為可具有硫鍵或醚鍵的2價~4價之烴基,R6為可經取代的1價~4價之烴基,Ar1及Ar2各自為可經取代的碳原子數6~20的伸芳基或芳基,n2為1之整數,n1、n3、n4、及n5各自為0或1之整數,n4與n5不同時為0之整數。〕所表示的基的第1觀點記載之微影術用阻劑底層膜形成組成物、第3觀點為,水解性有機矽烷為含有式(3):[化3]R1 aSi(R2)4-a 式(3)
(式(3)中,R1為烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、或彼等之組合,且藉由Si-C鍵結與矽原子鍵結者,R2為烷氧基、醯基氧基或鹵素基,a為0~3之整數。)、及式(4):[化4]〔R1 cSi(R2)3-c〕2Yb 式(4)
(式(4)中,R1為烷基,R2為烷氧基、醯基氧基或鹵素基,Y為伸烷基或伸芳基,b為0或1之整數,c為0或1之整數。)所成群中選出的至少1種之有機矽化合物與上述式(1)所表示的水解性有機矽烷之組合、與彼等
之水解物、或彼等之水解縮合物的第1觀點或第2觀點記載之微影術用阻劑底層膜形成組成物、第4觀點為,含有以上述式(1)所表示的化合物的水解縮合物、或上述式(1)所表示的化合物與式(3)所表示的化合物的水解縮合物作為聚合物的第1觀點~第3觀點中任一記載之阻劑底層膜形成組成物、第5觀點為進一步含有酸的第1觀點~第4觀點中任一記載之阻劑底層膜形成組成物、第6觀點為進一步含有水的第1觀點~第5觀點中任一記載之阻劑底層膜形成組成物、第7觀點為進一步含有銨化合物、環狀銨化合物、環狀胺化合物、或鋶化合物的第1觀點~第6觀點中任一記載之阻劑底層膜形成組成物、第8觀點為藉由將第1觀點~第7觀點中任一記載之阻劑底層膜形成組成物塗佈於半導體基板上並燒成而得到的阻劑底層膜、第9觀點為包含將第1觀點~第7觀點中任一記載之阻劑底層膜形成組成物塗佈於半導體基板上、進行燒成而形成阻劑底層膜之步驟、在前述阻劑底層膜上塗佈阻劑用組成物並形成阻劑膜之步驟、使前述阻劑膜曝光之步驟、曝光後將前述阻劑膜顯影而得到阻劑圖型之步驟、藉由該阻劑圖型將前述阻劑底層膜蝕刻之步驟、及藉由經圖型化的前述阻劑膜與前述阻劑底層膜將前述半導體基板加工之步驟的半導體裝置的製造方法、
第10觀點為包含在半導體基板上形成有機底層膜之步驟、於其上塗佈第1觀點~第7觀點中任一記載之阻劑底層膜形成組成物並燒成,形成阻劑底層膜之步驟、在前述阻劑底層膜上塗佈阻劑用組成物並形成阻劑膜之步驟、使前述阻劑膜曝光之步驟、曝光後將前述阻劑膜顯影而得到阻劑圖型之步驟、藉由前述阻劑圖型使前述阻劑底層膜進行蝕刻之步驟、藉由經圖型化的前述阻劑底層膜將前述有機底層膜蝕刻之步驟、及藉由經圖型化的前述有機底層膜將前述半導體基板加工之步驟的半導體裝置的製造方法、及第11觀點為下述式(5):[化5](R 3 ) a Si(R 2 ) (4-a) 式(5)
〔式(5)中,R2為烷氧基、醯基氧基、或鹵素基。a為1之整數。R3為下述式(6):
(式(6)中,R4、Ar1、R5、Ar2、及R6之有機基之中1個有機基為以Si-C鍵結與Si原子鍵結者,R4為可具有硫鍵或醚鍵的1價~4價之烴基,R5為可具有硫鍵或醚鍵的2價~4價之烴基,R6為可經取代的1價~4價之烴基,Ar1及Ar2各自為可經取代的伸苯基或苯基,n2為1
之整數,n1、n3、n4、及n5各自為0或1之整數,n4與n5不同時為0之整數。)所表示的基。〕所表示的化合物。
在本發明,在基板上使阻劑底層膜藉由塗佈法形成、或透過基板上的有機底層膜於其上使阻劑底層膜以塗佈法形成,並於該阻劑底層膜上形成阻劑膜(例如光阻、電子線阻劑、EUV阻劑)。接著,經曝光與顯影形成阻劑圖型,使用該阻劑圖型將阻劑底層膜進行乾蝕刻後,進行圖型之轉印,藉由該圖型進行基板加工、或藉由將有機底層膜進行蝕刻而將圖型轉印,並藉由該有機底層膜進行基板之加工。
除了形成微細圖型,為了防止圖型倒塌而有阻劑膜厚變薄之傾向。因阻劑的薄膜化而於其底層存在之膜上轉印圖型用的乾蝕刻,若不比上層的膜之蝕刻速度高則無法圖型轉印。在本發明,於基板上透過有機底層膜、或不透過有機底層膜,使其上以本發明阻劑底層膜(含無機系矽系化合物)被覆,進而使其上以阻劑膜(有機阻劑膜)被覆。有機系成分之膜與無機系成分之膜因蝕刻氣體的選擇而乾蝕刻速度有大差異,有機系成分之膜以氧系氣體乾蝕刻速度變高、無機系成分之膜以含鹵素氣體乾蝕刻速度變高。
例如形成阻劑圖型、使在該底層存在的本發明阻劑底層膜以含鹵素氣體進行乾蝕刻,在阻劑底層膜轉印圖型,
在轉印於該阻劑底層膜的圖型使用含鹵素氣體進行基板加工。或使用經圖型轉印的阻劑底層膜,使該底層的有機底層膜以氧系氣體進行乾蝕刻,於有機底層膜進行圖型轉印,在該經圖型轉印的有機底層膜,使用含鹵素氣體進行基板加工。
在本發明,該阻劑底層膜為具有作為硬遮罩機能者、上述式(1)之構造中之烷氧基或醯基氧基、鹵素基等之水解性基進行水解~部分水解,之後藉由矽烷醇基的縮合反應而形成聚矽氧烷構造的聚合物。此聚有機矽氧烷構造具有作為硬遮罩之充分機能。
接著,聚有機矽氧烷構造(中間膜),在其下存在之有機底層膜的蝕刻或基板之加工(蝕刻)可作為硬遮罩。
亦即、為對於基板加工時或有機底層膜的蝕刻所使用的氧系乾蝕刻氣體具有充分耐乾蝕刻性者。
本發明之阻劑底層膜為具備對此等之上層阻劑的乾蝕刻速度的提升、與基板加工時等之耐乾蝕刻性者。
本發明之阻劑底層膜形成組成物的阻劑底層膜,因含有含磺醯基與吸光基的有機基之矽烷化合物、其水解物、或其水解縮合物,曝光與顯影後之阻劑圖型的形狀成為矩形。藉此可進行微細圖型之基板加工。
例如專利文獻1記載之使用具有磺醯胺基的矽烷化合物的阻劑底層膜之阻劑圖型雖易有腳化傾向,但本發明之使用具有碸構造之矽烷化合物的阻劑底層膜可改善阻劑圖型之腳化傾向。
本發明係關於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,且該矽烷為上述式(1)之微影術用阻劑底層膜形成組成物。
相對矽烷全體的矽原子,式(1)之R3所表示之含有磺醯基與吸光基,且以Si-C鍵結與Si原子鍵結的有機基可以含有未達50莫耳%、例如0.5~30莫耳%、0.5~25莫耳%、0.5~15莫耳%、或0.5~10莫耳%之比例。
本發明之阻劑底層膜形成組成物含有式(1)所表示的水解性有機矽烷、其水解物、或其水解縮合物、與溶劑。而且作為任意成分可含有酸、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。
本發明之阻劑底層膜形成組成物之固形分,例如為0.1質量%~50質量%、或0.1質量%~30質量%、0.1質量%~25質量%。在此固形分係指由阻劑底層膜形成組成物的全成分除去溶劑成分者。
固形分中所占的水解性有機矽烷、其水解物、及其水解縮合物的比例為20質量%以上、例如50質量%~100質量%、60質量%~100質量%、70質量%~100質量%。
本發明所使用的水解性有機矽烷具有式(1)所表示的構造。式(1)中,R3為含有磺醯基與吸光基,且以Si-
C鍵結與Si原子鍵結的有機基,R1為烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、或彼等之組合。R2可為烷氧基、醯基氧基、或鹵素基。a為0~2之整數,b為1~3之整數。而式(1)中,可選擇a可為0的整數、b為1之整數的構造。
上述吸光基為可吸收曝光光的有機基,例如苯環、萘環等之芳香族環或乙烯基等之含不飽和鍵結的基。宜使用以苯環為基礎的苯基或伸苯基。
上述式(1)之R3可使用上述式(2)之構造的有機基。式(2)中,R4、Ar1、R5、Ar2、及R6之基中1個~3個的有機基為以Si-C鍵結與Si原子鍵結者,R4為可具有硫鍵或醚鍵的1價~4價之烴基,R5為可具有硫鍵或醚鍵的2價~4價之烴基,Ar1及Ar2各自為可經取代的碳原子數6~20的伸芳基,n2為1之整數,n1、n3、n4、及n5各自為0或1之整數,n4與n5不同時為0之整數。
式(2)中,可選擇R4、Ar1、R5、Ar2、及R6之基中1個有機基以Si-C鍵結與Si原子鍵結之構造。
R4、R5、R6、Ar1、及Ar2可經取代,該取代基,可舉如下述鹵素基或烷氧基。鹵素基,可舉如氟、氯、溴、或碘,烷氧基可使用下述之例示。
上述烷基為具有直鏈或分枝之碳原子數1~碳原子數
10的烷基,例如甲基、乙基、n-丙基、i-丙基、n-丁基、i-丁基、s-丁基、t-丁基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基及1-乙基-2-甲基-n-丙基等。且亦可使用環狀烷基,例如碳原子數1~碳原子數10的環狀烷基,可舉例如環丙基、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-n-丙基-環丙基、2-n-丙基-環丙基、1-i-丙基-環丙基、2-i-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。
芳基,可舉例如碳原子數6~碳原子數20的芳基,例
如苯基、o-甲基苯基、m-甲基苯基、p-甲基苯基、o-氯苯基、m-氯苯基、p-氯苯基、o-氟苯基、p-巰基苯基、o-甲氧基苯基、p-甲氧基苯基、p-胺基苯基、p-氰基苯基、α-萘基、β-萘基、o-聯苯基、m-聯苯基、p-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,可舉例如碳原子數2~碳原子數10的烯基,例如乙烯基、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-n-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-i-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-n-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-n-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-s-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-i-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-i-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-n-丙基-1-丙烯基、1-n-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-t-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-i-丙基-1-丙烯基、1-i-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。
芳烷基為以芳基取代的烷基,例如以苯基取代的碳原子數1~碳原子數10的烷基,具體例如苄基、乙基苯基、丙基苯基、丁基苯基等。
又,可舉例如以氟、氯、溴、或碘等之鹵素原子取代的此等之有機基。
具有環氧基的有機基,可舉例如環氧丙氧基甲基、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,可舉例如丙烯醯基甲基、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,可舉例如甲基丙烯醯基甲基、甲基丙烯醯基乙基、甲基丙烯醯基丙基等。
具有巰基之有機基,可舉例如乙基巰基、丁基巰基、己基巰基、辛基巰基等。
具有烷氧基芳基之有機基為有烷氧基取代的芳基或具有彼等之芳基的有機基。此等之烷氧基或芳基為例示於上述或下述。
具有醯基氧基芳基之有機基為有醯基氧基取代的芳基或具有彼等之芳基的有機基。此等之醯基氧基或芳基可例示上述或下述。
具有異氰脲酸酯基之有機基,可舉例如異氰脲酸酯基或氰脲酸酯伸烷基,伸烷基可舉例如對應上述之烷基之基。該異氰脲酸酯基可以烯丙基等之烯基或縮水甘油基等之含環氧基之基或烷基等取代。
具有羥基之有機基,可舉例如羥基或羥基烷基或者羥基伸烷基。烷基可舉例如上述、伸烷基可舉例如對應烷基之基。
具有環狀胺基之有機基,可舉例如環狀胺基或環狀胺基伸烷基。環狀胺基,可舉例如咪唑基、4,5-二氫咪唑基
等。伸烷基可舉例如對應上述烷基之基。例如丙基咪唑基、丙基-4,5-二氫咪唑基等。此等可用作為環狀胺化合物。
具有氰基的有機基,可舉例如氰基乙基、氰基丙基等。
R4、R5、及R6為可經取代的1價~4價之烴基,例如碳原子數1~碳原子數10的烷基、伸烷基。烷基可使用上述之烷基,伸烷基為由上述烷基所衍生的2價或3價之烴基。Ar1及Ar2各自為可經取代的碳原子數6~碳原子數20的伸芳基。取代基,可舉例如鹵素原子、烷氧基等。鹵素原子、烷氧基可舉例如上述或下述之例示。
R4、R5、R6、Ar1及Ar2的取代基,可舉例如上述鹵素原子等。
可具有硫鍵或醚鍵之烴基,可舉例如-S-R-、-R-S-R-、-O-R-、-R-O-R-等之有機基。R可以Si-C鍵結與Si原子鍵結。在此R為上述之烷基或基於該烷基的伸烷基。
式(1)之碳原子數1~碳原子數20的烷氧基,可舉例如碳原子數1~碳原子數20的具有直鏈、分支、環狀之烷基部分的烷氧基,例如甲氧基、乙氧基、n-丙氧基、i-丙氧基、n-丁氧基、i-丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、1-甲基-n-丁氧基、2-甲基-n-丁氧基、3-甲基-n-丁氧基、1,1-二甲基-n-丙氧基、1,2-二甲基-n-丙氧基、2,2-二甲基-n-丙氧基、1-乙基-n-丙氧基、n-已氧基、1-甲基-n-戊氧基、2-甲基-n-戊氧基、3-甲基-n-戊氧基、4-甲基-
n-戊氧基、1,1-二甲基-n-丁氧基、1,2-二甲基-n-丁氧基、1,3-二甲基-n-丁氧基、2,2-二甲基-n-丁氧基、2,3-二甲基-n-丁氧基、3,3-二甲基-n-丁氧基、1-乙基-n-丁氧基、2-乙基-n-丁氧基、1,1,2-三甲基-n-丙氧基、1,2,2-三甲基-n-丙氧基、1-乙基-1-甲基-n-丙氧基及1-乙基-2-甲基-n-丙氧基等,又環狀之烷氧基,可舉例如環丙氧基、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、環已氧基、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-n-丙基-環丙氧基、2-n-丙基-環丙氧基、1-i-丙基-環丙氧基、2-i-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)之碳原子數2~碳原子數20的醯基氧基,例如甲基羰基氧基、乙基羰基氧基、n-丙基羰基氧基、i-丙基羰基氧基、n-丁基羰基氧基、i-丁基羰基氧基、s-丁基羰基氧基、t-丁基羰基氧基、n-戊基羰基氧基、1-甲基-n-丁基羰基氧基、2-甲基-n-丁基羰基氧基、3-甲基-n-丁基
羰基氧基、1,1-二甲基-n-丙基羰基氧基、1,2-二甲基-n-丙基羰基氧基、2,2-二甲基-n-丙基羰基氧基、1-乙基-n-丙基羰基氧基、n-己基羰基氧基、1-甲基-n-戊基羰基氧基、2-甲基-n-戊基羰基氧基、3-甲基-n-戊基羰基氧基、4-甲基-n-戊基羰基氧基、1,1-二甲基-n-丁基羰基氧基、1,2-二甲基-n-丁基羰基氧基、1,3-二甲基-n-丁基羰基氧基、2,2-二甲基-n-丁基羰基氧基、2,3-二甲基-n-丁基羰基氧基、3,3-二甲基-n-丁基羰基氧基、1-乙基-n-丁基羰基氧基、2-乙基-n-丁基羰基氧基、1,1,2-三甲基-n-丙基羰基氧基、1,2,2-三甲基-n-丙基羰基氧基、1-乙基-1-甲基-n-丙基羰基氧基、1-乙基-2-甲基-n-丙基羰基氧基、苯基羰基氧基、及甲苯磺醯基羰基氧基等。
式(1)之鹵素基,可舉例如氟、氯、溴、碘等。
上述(1)之水解性有機矽烷,例如以下例示。在下述式,Me為甲基,Et為乙基。
在本發明,可含有式(3)之水解性有機矽烷及式(4)之水解性有機矽烷所成群中選出的至少1種之有機矽化合物、與上述式(1)之水解性有機矽烷之組合、與彼等之水解物、或彼等之水解縮合物。
又,在本發明,可使用上述式(1)之水解性有機矽烷的水解縮合物、或式(1)之水解性有機矽烷與式(3)之水解性有機矽烷的水解縮合物。
在本發明,可併用式(1)所示之水解性有機矽烷、與式(3)之水解性有機矽烷。
亦即可併用式(1)所示之水解性有機矽烷、其水解
物、或其水解縮合物、與式(3)之含矽化合物、其水解物、或其水解縮合物。
上述式(1)之水解性有機矽烷與式(3)之含矽化合物之比例,可在莫耳比1:0~1:200的範圍使用。為了得到良好阻劑形狀,式(1)之水解性有機矽烷與式(3)之含矽化合物之比例,可在莫耳比1:199~1:2的範圍使用。
此等以作為水解縮合物(聚有機矽氧烷的聚合物)使用為佳、以使用式(1)所示之水解性有機矽烷與式(3)所示之水解性有機矽烷的水解縮合物(聚有機矽氧烷的聚合物)為佳。
式(3)所表示的水解性有機矽烷中之R1為烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、或彼等之組合,且藉由Si-C鍵結與矽原子鍵結者,R2為烷氧基、醯基氧基、或鹵素基,a為0~3之整數。
R1、及R2所表示之烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、進一步水解性基所含的烷氧基、醯基氧基、或鹵素基,可例示如上述式(1)記載者。
式(3)所示之水解性有機矽烷,例如四甲氧基矽烷、四氯矽烷、四乙醯氧基矽烷、四乙氧基矽烷、四n-丙氧基矽烷、四異丙氧基矽烷、四n-丁氧基矽烷、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、甲基三乙醯氧基矽烷、甲基三丁氧基矽烷、甲基三戊氧基矽烷、甲基三苯氧基矽烷、甲基三苄基氧基矽烷、甲基三苯乙基氧基矽烷、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二甲氧基矽烷、γ-環氧丙氧基丙基乙烯二乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙烯三甲氧基矽烷、乙烯三氯矽烷、乙烯三乙醯氧基矽烷、乙烯三乙氧基矽烷、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-巰基丙基三甲氧基矽烷、γ-巰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-巰基丙基甲基二甲氧基矽烷、γ-巰基甲基二乙氧基矽烷、甲基乙烯二甲氧基矽烷、甲基乙烯二乙氧基矽烷、苯基磺醯基胺基丙基三乙氧基矽烷、甲基磺醯基胺基丙基三乙氧基矽烷、苯基磺醯基胺基丙基三甲氧基矽烷、甲基磺醯基胺基丙基三甲氧基矽烷等。
尤以四甲氧基矽烷、四乙氧基矽烷等之四烷氧基矽烷、與苯基三甲氧基矽烷、苯基三乙氧基矽烷等之苯基三烷氧基矽烷的組合為佳。進一步以此等之組合與甲基三甲氧基矽烷、甲基三乙氧基矽烷等之烷基三烷氧基矽烷組合為佳。
上述(3)之水解性有機矽烷亦可例示如下構造。構造中之R2與式(3)之R2相同。
式(4)之水解性有機矽烷的R1為烷基,R2為烷氧基、醯基氧基、或鹵素基,Y為伸烷基或伸芳基,b為0或1之整數,c為0或1之整數。
上述烷基、烷氧基、醯基氧基、或鹵素基,可使用式(1)中例示者。又伸烷基、伸芳基可舉例如對應上述烷基、及芳基的2價之有機基。
式(4)之水解性有機矽烷,例如亞甲基雙三甲氧基矽烷、亞甲基雙三氯矽烷、亞甲基雙三乙醯氧基矽烷、伸乙基雙三乙氧基矽烷、伸乙基雙三氯矽烷、伸乙基雙三乙醯氧基矽烷、伸丙基雙三乙氧基矽烷、伸丁基雙三甲氧基矽烷、伸苯基雙三甲氧基矽烷、伸苯基雙三乙氧基矽烷、伸苯基雙甲基二乙氧基矽烷、伸苯基雙甲基二甲氧基矽
烷、伸萘基雙三甲氧基矽烷、雙三甲氧基二矽烷、雙三乙氧基二矽烷、雙乙基二乙氧基二矽烷、雙甲基二甲氧基二矽烷等。
又,本發明為式(5)所示之新穎矽烷化合物。式(5)中,R2為烷氧基、醯基氧基、或鹵素基。上述烷氧基、醯基氧基、及鹵素基,可舉例如上述例示。a為1之整數。
式(5)之R3為上述式(6)所示。式(6)中,R4、Ar1、R5、Ar2、及R6之有機基之中1個有機基為以Si-C鍵結與Si原子鍵結者,R4為可具有硫鍵或醚鍵的1價~4價之烴基,R5為可具有硫鍵或醚鍵的2價~4價之烴基,R6為可經取代的1價~4價之烴基,Ar1及Ar2各自為可經取代的伸苯基或苯基,n2為1之整數,n1、n3、n4、及n5各自為0或1之整數,n4與n5不同時為0之整數。上述烴基、及可具有硫鍵或醚鍵的1價~3價之烴基,可舉例如上述例示。
式(1)所表示的水解性有機矽烷與式(3)所示之水解性有機矽烷的水解縮合物的具體例,如下例示。
式(1)之水解性有機矽烷的水解縮合物(聚有機矽氧烷)、或式(1)之水解性有機矽烷與式(3)及/或式(4)之有機矽化合物的水解縮合物(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。此等之分子量為以GPC分析之聚苯乙烯換算所得到的分子量。
GPC的測定條件,例如可使用GPC裝置(商品名HLC-8220GPC、東曹股份公司製)、GPC管柱(商品名ShodexKF803L、KF802、KF801、昭和電工製)、管柱溫度40℃、溶離液(溶出溶劑)為四氫呋喃、流量(流速)為1.0ml/min、標準試料為聚苯乙烯(昭和電工股份公司製)進行。
烷氧基矽烷基、醯氧基矽烷基、或鹵素化矽烷基的水解,水解性基每1莫耳使用0.5莫耳~100莫耳、較佳為1莫耳~10莫耳之水。
又,水解性基每1莫耳可使用0.001莫耳~10莫耳、較佳為0.001莫耳~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℃。
水解可進行完全水解、或部分水解。亦即、水解縮合物中可殘存水解物或單體。
水解、縮合時,可使用觸媒。
水解觸媒,可舉例如金屬螯合物化合物、有機酸、無機酸、有機鹼、無機鹼。
作為水解觸媒的金屬螯合物化合物,例如三乙氧基.單(乙醯基丙酮酸)鈦、三-n-丙氧基.單(乙醯基丙酮酸)鈦、三-i-丙氧基.單(乙醯基丙酮酸)鈦、三-n-丁氧基.單(乙醯基丙酮酸)鈦、三-sec-丁氧基.單(乙醯基丙酮酸)鈦、三-t-丁氧基.單(乙醯基丙酮酸)鈦、二乙氧基.雙(乙醯基丙酮酸)鈦、二-n-丙氧基.雙(乙醯基丙酮酸)鈦、二-i-丙氧基.雙(乙醯基丙酮酸)鈦、二-n-丁氧基.雙(乙醯基丙酮酸)鈦、二-sec-丁氧基.雙(乙醯基丙酮酸)鈦、二-t-丁氧基.雙(乙醯基丙酮酸)鈦、單乙氧基.參(乙醯基丙酮酸)鈦、單-n-丙氧基.參(乙醯基丙酮酸)鈦、單-i-丙氧基.參(乙醯基丙酮酸)鈦、單-n-丁氧基.參(乙醯基丙酮酸)鈦、單-sec-丁氧基.參(乙醯基丙酮酸)鈦、單-t-丁氧基.參(乙醯基丙酮酸)鈦、肆(乙醯基丙酮酸)鈦、三乙氧基.單(乙基乙醯乙酸酯)鈦、三-n-丙氧基.單(乙基乙醯乙酸酯)鈦、三-i-丙氧基.單(乙基乙醯乙酸酯)鈦、三-n-
丁氧基.單(乙基乙醯乙酸酯)鈦、三-sec-丁氧基.單(乙基乙醯乙酸酯)鈦、三-t-丁氧基.單(乙基乙醯乙酸酯)鈦、二乙氧基.雙(乙基乙醯乙酸酯)鈦、二-n-丙氧基.雙(乙基乙醯乙酸酯)鈦、二-i-丙氧基.雙(乙基乙醯乙酸酯)鈦、二-n-丁氧基.雙(乙基乙醯乙酸酯)鈦、二-sec-丁氧基.雙(乙基乙醯乙酸酯)鈦、二-t-丁氧基.雙(乙基乙醯乙酸酯)鈦、單乙氧基.參(乙基乙醯乙酸酯)鈦、單-n-丙氧基.參(乙基乙醯乙酸酯)鈦、單-i-丙氧基.參(乙基乙醯乙酸酯)鈦、單-n-丁氧基.參(乙基乙醯乙酸酯)鈦、單-sec-丁氧基.參(乙基乙醯乙酸酯)鈦、單-t-丁氧基.參(乙基乙醯乙酸酯)鈦、肆(乙基乙醯乙酸酯)鈦、單(乙醯基丙酮酸)參(乙基乙醯乙酸酯)鈦、雙(乙醯基丙酮酸)雙(乙基乙醯乙酸酯)鈦、參(乙醯基丙酮酸)單(乙基乙醯乙酸酯)鈦、等之鈦螯合物化合物;三乙氧基.單(乙醯基丙酮酸)鋯、三-n-丙氧基.單(乙醯基丙酮酸)鋯、三-i-丙氧基.單(乙醯基丙酮酸)鋯、三-n-丁氧基.單(乙醯基丙酮酸)鋯、三-sec-丁氧基.單(乙醯基丙酮酸)鋯、三-t-丁氧基.單(乙醯基丙酮酸)鋯、二乙氧基.雙(乙醯基丙酮酸)鋯、二-n-丙氧基.雙(乙醯基丙酮酸)鋯、二-i-丙氧基.雙(乙醯基丙酮酸)鋯、二-n-丁氧基.雙(乙醯基丙酮酸)鋯、二-sec-丁氧基.雙(乙醯基丙酮酸)鋯、二-t-丁氧基.雙(乙醯基丙酮酸)鋯、單乙氧基.參(乙醯基丙酮酸)鋯、單-n-丙氧基.參(乙醯基丙酮酸)鋯、
單-i-丙氧基.參(乙醯基丙酮酸)鋯、單-n-丁氧基.參(乙醯基丙酮酸)鋯、單-sec-丁氧基.參(乙醯基丙酮酸)鋯、單-t-丁氧基.參(乙醯基丙酮酸)鋯、肆(乙醯基丙酮酸)鋯、三乙氧基.單(乙基乙醯乙酸酯)鋯、三-n-丙氧基.單(乙基乙醯乙酸酯)鋯、三-i-丙氧基.單(乙基乙醯乙酸酯)鋯、三-n-丁氧基.單(乙基乙醯乙酸酯)鋯、三-sec-丁氧基.單(乙基乙醯乙酸酯)鋯、三-t-丁氧基.單(乙基乙醯乙酸酯)鋯、二乙氧基.雙(乙基乙醯乙酸酯)鋯、二-n-丙氧基.雙(乙基乙醯乙酸酯)鋯、二-i-丙氧基.雙(乙基乙醯乙酸酯)鋯、二-n-丁氧基.雙(乙基乙醯乙酸酯)鋯、二-sec-丁氧基.雙(乙基乙醯乙酸酯)鋯、二-t-丁氧基.雙(乙基乙醯乙酸酯)鋯、單乙氧基.參(乙基乙醯乙酸酯)鋯、單-n-丙氧基.參(乙基乙醯乙酸酯)鋯、單-i-丙氧基.參(乙基乙醯乙酸酯)鋯、單-n-丁氧基.參(乙基乙醯乙酸酯)鋯、單-sec-丁氧基.參(乙基乙醯乙酸酯)鋯、單-t-丁氧基.參(乙基乙醯乙酸酯)鋯、肆(乙基乙醯乙酸酯)鋯、單(乙醯基丙酮酸)參(乙基乙醯乙酸酯)鋯、雙(乙醯基丙酮酸)雙(乙基乙醯乙酸酯)鋯、參(乙醯基丙酮酸)單(乙基乙醯乙酸酯)鋯、等之鋯螯合物化合物;參(乙醯基丙酮酸)鋁、參(乙基乙醯乙酸酯)鋁等之鋁螯合物化合物;等。
作為水解觸媒的有機酸,例如乙酸、丙酸、丁烷酸、戊烷酸、己烷酸、庚烷酸、辛烷酸、壬烷酸、癸烷酸、草
酸、馬來酸、甲基丙二酸、己二酸、癸二酸、没食子酸、酪酸、偏苯三甲酸、花生烯四酸、米基米酸、2-乙基己烷酸、油酸、硬脂酸、亞麻油酸、次亞麻酸、水楊酸、安息香酸、p-胺基安息香酸、p-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、苯二甲酸、富馬酸、檸檬酸、酒石酸等。
作為水解觸媒的無機酸,可舉例如鹽酸、硝酸、硫酸、氟酸、磷酸等。
作為水解觸媒的有機鹼,例如吡啶、吡咯、哌嗪、吡咯烷、哌啶、甲吡啶、三甲基胺、三乙基胺、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、二氮雜雙環辛烷、二氮雜雙環壬烷、二氮雜雙環十一烯、四甲基氫氧化銨等。無機鹼,可舉例如氨、氫氧化鈉、氫氧化鉀、氫氧化鋇、氫氧化鈣等。此等觸媒中,以金屬螯合物化合物、有機酸、無機酸為佳、此等可1種或2種以上同時使用。
水解所使用的有機溶劑,可舉例如n-戊烷、i-戊烷、n-己烷、i-己烷、n-庚烷、i-庚烷、2,2,4-三甲基戊烷、n-辛烷、i-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、n-丙基苯、i-丙基苯、二乙基苯、i-丁基苯、三乙基苯、二-i-丙基苯、n-戊基萘、三甲基苯等之芳香族烴系溶劑;甲醇、乙醇、n-丙醇、i-丙醇、n-丁醇、i-丁醇、sec-丁醇、t-丁醇、n-戊醇、i-戊醇、2-甲基丁醇、sec-戊醇、t-戊
醇、3-甲氧基丁醇、n-己醇、2-甲基戊醇、sec-己醇、2-乙基丁醇、sec-庚醇、庚醇-3、n-辛醇、2-乙基己醇、sec-辛醇、n-壬基醇、2,6-二甲基庚醇-4、n-癸醇、sec-十一基醇、三甲基壬基醇、sec-四癸基醇、sec-十七基醇、酚、環己醇、甲基環己醇、3,3,5-三甲基環己醇、苄基醇、苯基甲基原醇、二丙酮醇、甲等之單醇系溶劑;乙二醇、丙二醇、1,3-丁二醇、戊烷二醇-2,4、2-甲基戊烷二醇-2,4、己烷二醇-2,5、庚烷二醇-2,4、2-乙基己烷二醇-1,3、二乙二醇、二丙二醇、三乙二醇、三丙二醇、甘油等之多價醇系溶劑;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-丁基酮、甲基-n-戊基酮、乙基-n-丁基酮、甲基-n-己基酮、二-i-丁基酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊烷二酮、丙酮基丙酮、二丙酮醇、乙醯苯、茴香酮等之酮系溶劑;乙基醚、i-丙基醚、n-丁基醚、n-己基醚、2-乙基己基醚、環氧乙烷、1,2-環氧丁烷、二氧戊環、4-甲基二氧戊環、二噁烷、二甲基二噁烷、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇二乙基醚、乙二醇單-n-丁基醚、乙二醇單-n-己基醚、乙二醇單苯基醚、乙二醇單-2-乙基丁基醚、乙二醇二丁基醚、二乙二醇單甲基醚、二乙二醇單乙基醚、二乙二醇二乙基醚、二乙二醇單-n-丁基醚、二乙二醇二-n-丁基醚、二乙二醇單-n-己基醚、乙氧基三二醇、四乙二醇二-n-丁基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單丙基醚、丙二醇單丁基醚、二丙二醇單甲基醚、二丙二醇單乙基醚、二
丙二醇單丙基醚、二丙二醇單丁基醚、三丙二醇單甲基醚、四氫呋喃、2-甲基四氫呋喃等之醚系溶劑;二乙基碳酸酯、乙酸甲酯、乙酸乙酯、γ-丁內酯、γ-戊內酯、乙酸n-丙酯、乙酸i-丙酯、乙酸n-丁酯、乙酸i-丁酯、乙酸sec-丁酯、乙酸n-戊酯、乙酸sec-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n-壬酯、乙醯乙酸甲酯、乙醯乙酸乙酯、乙酸乙二醇單甲基醚、乙酸乙二醇單乙基醚、乙酸二乙二醇單甲基醚、乙酸二乙二醇單乙基醚、乙酸二乙二醇單-n-丁基醚、乙酸丙二醇單甲基醚、乙酸丙二醇單乙基醚、乙酸丙二醇單丙基醚、乙酸丙二醇單丁基醚、乙酸二丙二醇單甲基醚、乙酸二丙二醇單乙基醚、二乙酸二醇、乙酸甲氧基三二醇、丙酸乙酯、丙酸n-丁酯、丙酸i-戊酯、草酸二乙酯、草酸二-n-丁酯、乳酸甲酯、乳酸乙酯、乳酸n-丁酯、乳酸n-戊酯、丙二酸二乙酯、苯二甲酸二甲酯、苯二甲酸二乙基等之酯系溶劑;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、二甲基亞碸、環丁碸、1,3-丙烷磺內酯等之含硫系溶劑等。此等之溶劑可1種或2種以上的組合使用。
尤其,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-丁基酮、甲基-n-戊基酮、乙
基-n-丁基酮、甲基-n-己基酮、二-i-丁基酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊烷二酮、丙酮基丙酮、二丙酮醇、乙醯苯、茴香酮(1,1,3-三甲基-2-降冰片烯)等之酮系溶劑在溶液保存安定性的點上為佳。
將水解性有機矽烷在溶劑中使用觸媒進行水解、縮合,得到的水解縮合物(聚合物)以減壓蒸餾等,可使副生成物的醇或使用的水解觸媒或水同時除去。又,可將水解使用的酸或鹼觸媒以中和或離子交換而除去。接著在本發明之微影術用阻劑底層膜形成組成物,含該水解縮合物的阻劑底層膜形成組成物為了安定化,可添加酸(例如有機酸)、水、醇、或彼等之組合。
上述有機酸,可舉例如草酸、丙二酸、甲基丙二酸、琥珀酸、馬來酸、蘋果酸、酒石酸、苯二甲酸、檸檬酸、戊二酸、檸檬酸、乳酸、水楊酸等。其中以草酸、馬來酸等為佳。加入的有機酸,相對縮合物(聚有機矽氧烷)100質量份而言,為0.5質量份~5.0質量份。又加入的水可使用純水、超純水、離子交換水等,其添加量相對阻劑底層膜形成組成物100質量份而言,可為1質量份~20質量份。
又加入的醇以經塗佈後之加熱而易飛散者為佳,例如甲醇、乙醇、丙醇、異丙醇、丁醇等。加入的醇,相對阻劑底層膜形成組成物100質量份而言,可為1質量份~20質量份。
又,添加劑,可添加雙酚S、或雙酚S衍生物。雙酚
S、或雙酚S衍生物,相對聚有機矽氧烷100質量份而言,為0.01質量份~20質量份、或0.01質量份~10質量份、或0.01質量份~5質量份。
較佳雙酚S、或雙酚S衍生物如下例示。
本發明之阻劑底層膜形成組成物可含有硬化觸媒。硬
化觸媒在使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,具有硬化觸媒之作用。
硬化觸媒,可使用銨鹽、膦類、鏻鹽、鋶鹽。
銨鹽方面,可舉例如具有式(D-1):
(但,m為2~11、n為2~3之整數、R1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-2):[化26]R2R3R4R5N+ Y- 式(D-2)
(但,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鍵結與氮原子鍵結者)所表示的構造之第4級銨鹽、具有式(D-3):
(但,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,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,R9及R10為烷基或芳基、Y-為陰離子)之構造之第4級銨鹽、具有式(D-6):
(但,m為2~11、n為2~3之整數、H為氫原子、Y-為陰離子)之構造的第3級銨鹽。
又,鏻鹽方面,可舉例如式(D-7):[化31]R11R12R13R14P+ Y- 式(D-7)
(但,R11、R12、R13、及R14為烷基或芳基、P為磷原子、Y-為陰離子,且R11、R12、R13、及R14各自為藉由
C-P鍵結與磷原子鍵結者)所示之第4級鏻鹽。
又,鋶鹽方面,可舉例如式(D-8):[化32]R15R16R17S+ Y- 式(D-8)
(但,R15、R16、及R17為烷基或芳基、S為硫原子、Y-為陰離子,且R15、R16、及R17各自為藉由C-S鍵結與硫原子鍵結者)所示之第3級鋶鹽。
上述式(D-1)之化合物為胺所衍生的第4級銨鹽,m為2~11、n為2~3之整數。該第4級銨鹽的R1為碳原子數1~碳原子數18、較佳為碳原子數2~碳原子數10的烷基或芳基,例如乙基、丙基、丁基等之直鏈烷基或苄基、環己基、環己基甲基、二環戊二烯基等。又陰離子(Y-)可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。
上述式(D-2)之化合物為R2R3R4R5N+ Y-所表示之第4級銨鹽。該第4級銨鹽的R2、R3、R4及R5為碳原子數1~碳原子數18之烷基或芳基、或藉由Si-C鍵結與矽原子鍵結的矽烷化合物。陰離子(Y-),可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。該第4級銨鹽,可以市售品取得,例如四甲基銨乙酸酯、四丁基銨乙酸酯、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。此等可以銨化合物添加。
上述式(D-3)之化合物為1-取代咪唑所衍生的第4級銨鹽,R6及R7為碳原子數1~碳原子數18、R6及R7的碳原子數總和以具有7以上為佳。例如R6為甲基、乙基、丙基、苯基、苄基、藉由Si-C鍵結與矽原子鍵結的矽烷化合物、或此等之組合。R7可舉例如苄基、辛基、十八基。陰離子(Y-)可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。此化合物亦可以市售品取,例如可使1-甲基咪唑、1-苄基咪唑等之咪唑系化合物、與溴化苄酯、溴化甲酯等之鹵素化烷酯或鹵素化芳酯反應而製造。又,式(D-3)之化合物,可以4位與5位經氫化的4,5-二氫咪唑化合物使用,例如N-(3-三乙氧基矽烷基丙基)-4,5-二氫咪唑等。此等可作為環狀銨化合物添加。
上述式(D-4)之化合物為吡啶所衍生的第4級銨鹽,R8為碳原子數1~碳原子數18、較佳為碳原子數4~碳原子數18之烷基或芳基,例如丁基、辛基、苄基、月桂基。陰離子(Y-)可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。此化合物亦可以市售品取得,但例如可使吡啶與氯化月桂酯、氯化苄酯、溴化苄酯、溴化甲酯、溴化辛酯等之鹵素化烷酯、或鹵素化芳酯反應而製造。此化合物可舉例如氯化N-月
桂基吡啶鎓、溴化N-苄基吡啶鎓等。
上述式(D-5)之化合物為以甲吡啶等代表的取代吡啶所衍生的第4級銨鹽,R9為碳原子數1~碳原子數18、較佳為碳原子數4~碳原子數18之烷基或芳基,例如甲基、辛基、月桂基、苄基等。R10為碳原子數1~碳原子數18之烷基或芳基,例如為甲吡啶所衍生的第4級銨之場合,R10為甲基。陰離子(Y-)可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。此化合物亦可以市售品取得,但例如可以甲吡啶等之取代吡啶與溴化甲酯、溴化辛酯、氯化月桂酯、氯化苄酯、溴化苄酯等之鹵素化烷酯、或鹵素化芳酯反應而製造。此化合物,可舉例如N-苄基吡啶鎓鹽化物、N-苄基吡啶鎓溴化物、N-月桂基吡啶鎓鹽化物等。
上述式(D-6)之化合物為胺所衍生的第3級銨鹽,m為2~11、n為2~3之整數。又陰離子(Y-)可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。可藉由胺與羧酸或酚等之弱酸的反應而製造。羧酸可舉例如甲酸或乙酸,使用甲酸之場合,陰離子(Y-)為(HCOO-),使用乙酸之場合,陰離子(Y-)為(CH3COO-)。又使用酚之場合,陰離子(Y-)為(C6H5O-)。
上述式(D-7)之化合物為具有R11R12R13R14P+ Y-之
構造的第4級鏻鹽。R11、R12、R13、及R14為碳原子數1~碳原子數18之烷基或芳基、或藉由Si-C鍵結與矽原子鍵結的矽烷化合物,但較佳為R11~R14之4個取代基中3個為苯基或經取代的苯基,例如苯基或甲苯基,又剩下的1個為碳原子數1~碳原子數18之烷基、芳基、或藉由Si-C鍵結與矽原子鍵結的矽烷化合物。又陰離子(Y-)可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。此化合物可以市售品取得,例如鹵素化四n-丁基鏻、鹵素化四n-丙基鏻等之鹵素化四烷基鏻、鹵素化三乙基苄基鏻等之鹵素化三烷基苄基鏻、鹵素化三苯基甲基鏻、鹵素化三苯基乙基鏻等之鹵素化三苯基單烷基鏻、鹵素化三苯基苄基鏻、鹵素化四苯基鏻、鹵素化三甲苯基單芳基鏻、或鹵素化三甲苯基單烷基鏻(鹵素原子為氯原子或溴原子)。尤其,鹵素化三苯基甲基鏻、鹵素化三苯基乙基鏻等之鹵素化三苯基單烷基鏻、鹵素化三苯基苄基鏻等之鹵素化三苯基單芳基鏻、鹵素化三甲苯基單苯基鏻等之鹵素化三甲苯基單芳基鏻或鹵素化三甲苯基單甲基鏻等之鹵素化三甲苯基單烷基鏻(鹵素原子為氯原子或溴原子)為佳。
又,膦類,可舉例如甲基膦、乙基膦、丙基膦、異丙基膦、異丁基膦、苯基膦等之第一膦、二甲基膦、二乙基膦、二異丙基膦、二異戊基膦、二苯基膦等之第二膦、三甲基膦、三乙基膦、三苯基膦、甲基二苯基膦、二甲基苯
基膦等之第三膦。
上述式(D-8)之化合物為具有R15R16R17S+ Y-之構造的第3級鋶鹽。R15、R16、及R17為碳原子數1~碳原子數18之烷基或芳基、或藉由Si-C鍵結與矽原子鍵結的矽烷化合物,但較佳為R15~R17之3個取代基中2個為苯基或經取代的苯基,例如苯基或甲苯基,又剩下的1個為碳原子數1~碳原子數18之可具有取代的烷基、或芳基。又陰離子(Y-)可舉例如氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子或羧酸根(-COO-)、磺酸根(-SO3 -)、氧根(-O-)等之酸基。此化合物可以市售品取得,例如鹵素化三n-丁基鋶、鹵素化三n-丙基鋶等之鹵素化四烷基鏻、鹵素化二乙基苄基鋶等之鹵素化三烷基苄基鋶、鹵素化二苯基甲基鋶、鹵素化二苯基乙基鋶等之鹵素化二苯基單烷基鋶、鹵素化三苯基鋶、(鹵素原子為氯原子或溴原子)、三n-丁基鋶羧酸酯、三n-丙基鋶羧酸酯等之四烷基鏻羧酸酯、二乙基苄基鋶羧酸酯等之三烷基苄基鋶羧酸酯、二苯基甲基鋶羧酸酯、二苯基乙基鋶羧酸酯等之二苯基單烷基鋶羧酸酯、三苯基鋶羧酸酯、三苯基鋶三氟甲烷磺酸酯等。尤其,鹵素化三苯基鋶、三苯基鋶羧酸酯、例如馬來酸單三苯基鋶為佳。此等可作為鋶化合物添加。
硬化觸媒,相對聚有機矽氧烷100質量份而言,為0.01質量份~10質量份、或0.01質量份~5質量份、或0.01質量份~3質量份。
本發明之微影術用底層膜形成組成物,除上述成分之外,可含有因應必要的有機聚合物化合物、光酸產生劑及界面活性劑等。
藉由使用有機聚合物化合物,可調整本發明之微影術用底層膜形成組成物所形成之阻劑底層膜的乾蝕刻速度(每單位時間之膜厚減少量)、衰減係數及折射率等。
有機聚合物化合物方面無特別限制、可使用種種有機聚合物。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、丙烯系聚合物、甲基丙烯聚合物、聚乙烯醚、酚酚醛清漆、萘酚酚醛清漆、聚醚、聚醯胺、聚碳酸酯等之加成聚合聚合物及縮聚合聚合物。以使用具有作為吸光部位機能的苯環、萘環、蒽環、三嗪環、喹啉環、及喹喔啉環等之芳香環構造的有機聚合物為佳。
如此之有機聚合物化合物,例如含有以苄基丙烯酸酯、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-苯基馬來醯亞胺等之加成聚合性單體作為其構造單元的加成聚合聚合物或酚酚醛清漆及萘酚酚醛清漆等之縮聚合聚合物。
作為有機聚合物化合物,使用加成聚合聚合物之場合,該聚合物化合物可為單獨聚合物或共聚合物。加成聚合聚合物的製造中,可使用加成聚合性單體。如此之加成聚合性單體方面,可舉例如丙烯酸、甲基丙烯酸、丙烯酸
酯化合物、甲基丙烯酸酯化合物、甲基丙烯醯胺化合物、丙烯醯胺化合物、乙烯化合物、苯乙烯化合物、馬來醯亞胺化合物、馬來酸無水物、丙烯腈等。
丙烯酸酯化合物,可舉例如甲基丙烯酸酯、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-丙烯醯基氧基-6-羥基降冰片烯-2-羧酸-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,可舉例如甲基甲基丙烯酸酯、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-甲基丙烯醯基氧基-6-羥基降冰片烯-2-羧酸-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,可舉例如丙烯醯胺、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,可舉例如甲基丙烯醯胺、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。
乙烯化合物,可舉例如乙烯醇、2-羥基乙基乙烯醚、甲基乙烯醚、乙基乙烯醚、苄基乙烯醚、乙烯乙酸、乙烯三甲氧基矽烷、2-氯乙基乙烯醚、2-甲氧基乙基乙烯醚、乙烯萘及乙烯蒽等。
苯乙烯化合物,可舉例如苯乙烯、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,可舉例如馬來醯亞胺、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之場合,如此之聚合物,可舉例如二醇化合物與二羧酸化合物之縮聚合聚合物。二醇化合物方面,可舉例如二乙二醇、六亞甲基二醇、丁二醇等。二羧酸化合物,可舉例如琥珀酸、己二酸、對苯二甲酸、無水馬來酸等。又,例如聚均苯四甲醯亞胺、聚(p-伸苯基對苯二甲醯胺)、聚丙烯對苯二甲酸酯、聚乙烯對苯二甲酸酯等之聚酯、聚醯胺、聚醯亞胺。
有機聚合物化合物含有羥基之場合,該羥基可與聚有機矽氧烷產生交聯反應。
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。
有機聚合物化合物可僅使用一種、或二種以上組合使用。
使用有機聚合物化合物之場合,其比例相對縮合物(聚有機矽氧烷)100質量份為1質量份~200質量份、或5質量份~100質量份、或10質量份~50質量份、或20質量份~30質量份。
本發明之阻劑底層膜形成組成物可含有酸產生劑。
酸產生劑,可舉例如熱酸產生劑或光酸產生劑。
光酸產生劑在阻劑的曝光時產生酸。因此,可調整底層膜的酸性度。此為使底層膜的酸性度配合上層的阻劑之酸性度用的方法之一,藉由底層膜的酸性度的調整,可調整於上層形成之阻劑的圖型形狀。
本發明之阻劑底層膜形成組成物所含的光酸產生劑,可舉例如鎓鹽化合物、磺醯亞胺化合物、及二磺醯基二偶氮甲烷化合物等。
鎓鹽化合物方面,可舉例如二苯基碘鎓六氟磷酸酯、二苯基碘鎓三氟甲烷磺酸酯、二苯基碘鎓九氟正丁烷磺酸酯、二苯基碘鎓全氟正辛烷磺酸酯、二苯基碘鎓樟腦磺酸酯、雙(4-tert-丁基苯基)碘鎓樟腦磺酸酯及雙(4-tert-
丁基苯基)碘鎓三氟甲烷磺酸酯等之碘鎓鹽化合物、及三苯基鋶六氟銻酸酯、三苯基鋶九氟正丁烷磺酸酯、三苯基鋶樟腦磺酸酯及三苯基鋶三氟甲烷磺酸酯等之鋶氯化合物等。
磺醯亞胺化合物,可舉例如N-(三氟甲烷磺醯基氧基)琥珀醯亞胺、N-(九氟正丁烷磺醯基氧基)琥珀醯亞胺、N-(樟腦磺醯基氧基)琥珀醯亞胺及N-(三氟甲烷磺醯基氧基)萘二甲醯亞胺等。
二磺醯基二偶氮甲烷化合物,例如雙(三氟甲基磺醯基)二偶氮甲烷、雙(環己基磺醯基)二偶氮甲烷、雙(苯基磺醯基)二偶氮甲烷、雙(p-甲苯磺醯基)二偶氮甲烷、雙(2,4-二甲基苯磺醯基)二偶氮甲烷、及甲基磺醯基-p-甲苯磺醯基二偶氮甲烷等。
光酸產生劑可僅使用一種、或二種以上組合使用。
使用光酸產生劑之場合,其比例方面,相對縮合物(聚有機矽氧烷)100質量份為0.01質量份~5質量份、或0.1質量份~3質量份、或0.5質量份~1質量份。
界面活性劑,將本發明之微影術用阻劑底層膜形成組成物塗佈於基板時,可有效抑制針孔及變形等之產生。
本發明之阻劑底層膜形成組成物所含的界面活性劑,例如聚氧化乙烯月桂基醚、聚氧化乙烯硬脂醯醚、聚氧化乙烯十六基醚、聚氧化乙烯油基醚等之聚氧化乙烯烷基醚類、聚氧化乙烯辛基酚醚、聚氧化乙烯壬基酚醚等之聚氧化乙烯烷基芳基醚類、聚氧化乙烯.聚氧化丙烯嵌段共聚
合物類、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之山梨糖醇酐脂肪酸酯類、聚氧化乙烯山梨糖醇酐單月桂酸酯、聚氧化乙烯山梨糖醇酐單棕櫚酸酯、聚氧化乙烯山梨糖醇酐單硬脂酸酯、聚氧化乙烯山梨糖醇酐三油酸酯、聚氧化乙烯山梨糖醇酐三硬脂酸酯等之聚氧化乙烯山梨糖醇酐脂肪酸酯類等之非離子系界面活性劑、商品名EFTOPEF301、EF303、EF352((股)Thochem Products.製)、商品名MEGAFACEF171、F173、R-08、R-30(大日本油墨化學工業(股)製)、FluoradFC430、FC431(住友3M(股)製)、商品名AsahiGuardAG710,SurflonS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(股)製)等之氟系界面活性劑、及有機矽氧烷聚合物KP341(信越化學工業(股)製)等。此等之界面活性劑可單獨使用或二種以上組合使用。使用界面活性劑之場合,其比例方面,相對縮合物(聚有機矽氧烷)100質量份為0.0001質量份~5質量份、或0.001質量份~1質量份、或0.01質量份~0.5質量份。
又,本發明之阻劑底層膜形成組成物中,可添加流變學調整劑及接著輔助劑等。流變學調整劑有效使底層膜形成組成物的流動性提升。接著輔助劑有效提升半導體基板或阻劑與底層膜的密著性。
本發明之阻劑底層膜形成組成物所使用的溶劑,為可
將前述固形分溶解的溶劑,則無特別限制皆可使用。如此之溶劑,例如甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、丙二醇、丙二醇單甲基醚、丙二醇單乙基醚、甲基異丁基原醇、丙二醇單丁基醚、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、丙二醇單丁基醚乙酸酯、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-甲基丁烷酸甲酯、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、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚、乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、乙二醇單丙基醚乙酸酯、乙二醇單丁基醚乙酸酯、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二丙基醚、二乙二醇二丁基醚、丙二醇二甲基醚、丙二醇二乙基醚、丙二醇二丙基醚、丙二醇二丁基醚、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、酪酸甲酯、酪酸乙酯、酪酸丙酯、酪酸異丙酯、酪酸丁酯、酪酸異丁酯、3-甲氧基-2-甲基丙酸甲酯、2-羥基-3-甲基酪酸甲酯、甲氧基乙酸乙酯、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-甲氧基丁基丁酯、乙醯乙酸甲酯、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、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、4-甲基-2-戊醇、及γ-丁內酯等。此等之溶劑可單獨、或使用二種以上的組合。
以下、說明本發明之阻劑底層膜形成組成物的使用。
於半導體裝置的製造所使用的基板(例如矽晶圓基板、矽/二氧化矽被覆基板、矽氮化物基板、玻璃基板、ITO基板、聚醯亞胺基板、及低介電率材料(low-k材料)被覆基板等)之上,以旋轉器、塗佈器等之適當塗佈方法塗佈本發明之阻劑底層膜形成組成物,之後藉由燒成形成阻劑底層膜。燒成條件方面由燒成溫度80℃~250℃、燒成時間0.3分鐘~60分鐘中適宜選擇。較佳為燒成溫度150℃~250℃、燒成時間0.5分鐘~2分鐘。在此,形成之底層膜的膜厚,例如10nm~1000nm、或20nm~500nm、或50nm~300nm、或100nm~200nm。
接著,在該阻劑底層膜上形成例如光阻的層。光阻的層的形成可藉由習知方法、亦即、光阻組成物溶液塗佈於底層膜上及燒成而進行。光阻的膜厚,例如50nm~10000nm、或100nm~2000nm、或200nm~1000nm。
在本發明,基板上使有機底層膜成膜後,於其上使本發明之阻劑底層膜成膜,進一步可於其上被覆光阻。藉此光阻的圖型寬變窄,即使在為了防止圖型倒塌,而使光阻
薄薄地被覆之場合,藉由適當選擇蝕刻氣體,可進行基板之加工。例如可使用對光阻具有夠快蝕刻速度之氟系氣體作為蝕刻氣體,加工本發明之阻劑底層膜、又可使用對本發明之阻劑底層膜具有夠快蝕刻速度的氧系氣體作為蝕刻氣體,加工有機底層膜、進一步可使用對有機底層膜具有夠快蝕刻速度的氟系氣體作為蝕刻氣體,進行基板之加工。
本發明之阻劑底層膜上所形成的光阻,為對曝光所使用的光感光者即無特別限定。可使用負型光阻或正型光阻。有酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所構成之正型光阻、具有因酸而分解使鹼溶解速度上昇之基的黏合劑與光酸產生劑所構成之化學增幅型光阻、因酸而分解使光阻之鹼溶解速度上昇的低分子化合物與鹼可溶性黏合劑與光酸產生劑所構成之化學增幅型光阻、及具有因酸而分解使鹼溶解速度上昇之基的黏合劑與因酸而分解使光阻之鹼溶解速度上昇的低分子化合物與光酸產生劑所構成之化學增幅型光阻等。例如西普雷公司製商品名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。又,例如Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)、或Proc.SPIE,Vol.3999,365-374(2000)所記載般、含氟原子聚合物系光阻。
接著,通過特定遮罩進行曝光。曝光可使用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、亦可因應必要進行曝光後加熱(post exposure bake)。曝光後加熱為以加熱溫度70℃~150℃、加熱時間0.3分鐘~10分鐘所適宜選擇的條件進行。
又,在本發明,作為阻劑,改變為光阻可使用電子線微影術用阻劑、或EUV微影術用阻劑。電子線阻劑可使用負型、或正型。有酸產生劑與具有因酸分解而改變鹼溶解速度之基的黏合劑所構成之化學增幅型阻劑、鹼可溶性黏合劑與酸產生劑與酸而分解改變阻劑的鹼溶解速度之低分子化合物所構成之化學增幅型阻劑、由酸產生劑與具有藉由酸而分解改變鹼溶解速度之基的黏合劑與因酸而分解改變阻劑的鹼溶解速度之低分子化合物所構成之化學增幅型阻劑、具有因電子線而分解改變鹼溶解速度之基之黏合劑所構成之非化學增幅型阻劑、具有因電子線而被切斷改變鹼溶解速度之部位的黏合劑所構成之非化學增幅型阻劑等。即使使用此等之電子線阻劑的場合,可與照射源為電子線、使用光阻的場合,同樣地形成阻劑圖型。又,EUV阻劑可使用甲基丙烯酸酯樹脂系阻劑。
接著,以顯影液(例如鹼顯影液)進行顯影。藉此、例如使用正型光阻的場合,經曝光的部分之光阻被除去、形成光阻的圖型。
顯影液,可舉例如氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物的水溶液、氫氧化四甲基銨、氫氧化四乙基銨、膽鹼等之氫氧化四級銨的水溶液、乙醇胺、丙基胺、乙二胺
等之胺水溶液等之鹼性水溶液。進一步,此等之顯影液中亦可加入界面活性劑等。顯影的條件由溫度5℃~50℃、時間10秒~600秒中適宜選擇。
又,在本發明,顯影液可使用有機溶劑。曝光後以顯影液(溶劑)進行顯影。藉此、例如使用正型光阻的場合,未曝光部分之光阻被除去,形成光阻的圖型。
顯影液,例如乙酸甲酯、乙酸丁酯、乙酸乙酯、乙酸異丙酯、乙酸戊酯、乙酸異戊酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、丙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、乙二醇單丙基醚乙酸酯、乙二醇單丁基醚乙酸酯、乙二醇單苯基醚乙酸酯、二乙二醇單甲基醚乙酸酯、二乙二醇單丙基醚乙酸酯、二乙二醇單乙基醚乙酸酯、二乙二醇單苯基醚乙酸酯、二乙二醇單丁基醚乙酸酯、2-甲氧基丁基乙酸酯、3-甲氧基丁基乙酸酯、4-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-乙基-3-甲氧基丁基乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、2-乙氧基丁基乙酸酯、4-乙氧基丁基乙酸酯、4-丙氧基丁基乙酸酯、2-甲氧基戊基乙酸酯、3-甲氧基戊基乙酸酯、4-甲氧基戊基乙酸酯、2-甲基-3-甲氧基戊基乙酸酯、3-甲基-3-甲氧基戊基乙酸酯、3-甲基-4-甲氧基戊基乙酸酯、4-甲基-4-甲氧基戊基乙酸酯、丙二醇二乙酸酯、甲酸甲酯、甲酸乙酯、甲酸丁酯、甲酸丙酯、乳酸乙酯、乳酸丁酯、乳酸丙酯、碳酸乙酯、碳酸丙酯、碳酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、丙酮酸丁酯、乙醯乙
酸甲酯、乙醯乙酸乙酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、2-羥基丙酸甲酯、2-羥基丙酸乙酯、甲基-3-甲氧基丙酸酯、乙基-3-甲氧基丙酸酯、乙基-3-乙氧基丙酸酯、丙基-3-甲氧基丙酸酯、2-庚酮、3-庚酮、4-庚酮、4-甲基-2-戊醇等。進一步,此等之顯影液中亦可加入界面活性劑等。顯影的條件係由溫度5℃~50℃、時間10秒~600秒中適宜選擇。
接著,將如此所形成之光阻(上層)之圖型作為保護膜,進行本發明之阻劑底層膜(中間層)之除去,接著,以經圖型化的光阻及本發明之阻劑底層膜(中間層)所構成之膜作為保護膜,進行有機底層膜(底層)之除去。最後以經圖型化的本發明之阻劑底層膜(中間層)及有機底層膜(底層)作為保護膜,進行半導體基板之加工。
首先,使光阻被除去部分之本發明之阻劑底層膜(中間層)以乾蝕刻除去、使半導體基板露出。在本發明之阻劑底層膜的乾蝕刻,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之氣體。阻劑底層膜的乾蝕刻以使用鹵素系氣體為佳。在鹵素系氣體之乾蝕刻,基本上有機物質所構成之光阻不易被除去。相對於此,含多量矽原子的本發明之阻劑底層膜以鹵素系氣體快速被除去。因此,可抑制伴隨阻劑底層膜的乾蝕刻之光阻的膜厚減少。接著,結果光阻可以薄膜使用。阻劑底層膜的乾蝕
刻以氟系氣體進行為佳、氟系氣體,例如四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷、及二氟甲烷(CH2F2)等。
之後、以經圖型化的光阻及本發明之阻劑底層膜所構成之膜作為保護膜,進行有機底層膜的除去。有機底層膜(底層)以使用氧系氣體之乾蝕刻進行為佳。因含多量矽原子的本發明之阻劑底層膜,在氧系氣體之乾蝕刻不易被除去。氧系氣體的具體例,可舉例如O2及O3。
最後,進行半導體基板之加工。半導體基板之加工以氟系氣體之乾蝕刻進行為佳。
氟系氣體,例如四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷、及二氟甲烷(CH2F2)等。
又,在本發明之阻劑底層膜上層,於光阻的形成前可形成有機系之防反射膜。在此使用的防反射膜組成物方面無特別限制,可由目前微影術製程中,慣用者中任意選擇使用,又,慣用方法、例如可藉由旋轉器、塗佈器之塗佈及燒成,進行防反射膜的形成。
又,塗佈有本發明之阻劑底層膜形成組成物之基板,可為於其表面有以CVD法等形成的有機系或無機系之防反射膜者、或可於其上形成本發明之底層膜。
本發明之阻劑底層膜形成組成物所形成的阻劑底層膜,又,於微影術製程中,因使用光的波長而有吸收該光之情形。接著,如此之場合,可作為具有防止來自基板之
反射光效果的防反射膜。進一步,本發明之底層膜,亦可用作為防止基板與光阻之相互作用用的層、具有防止光阻所使用的材料或對光阻曝光時生成物質之對基板的負面影響的機能之層、具有防止加熱燒成時,基板所生成的物質擴散至上層光阻的機能之層、及減少因半導體基板介電體層之光阻層的污染效果用的障壁層等。
又,阻劑底層膜形成組成物所形成的阻劑底層膜,適用雙重金屬鑲嵌製程可使用的形成有介層洞的基板,可用作為可使孔洞無間隙充填的包埋材。又,亦可用作為使具凹凸的半導體基板之表面平坦化用的平坦化材。
又,作為EUV阻劑的底層膜,亦可用於作為硬遮罩機能以外之以下目的。作為不與EUV阻劑互混、可防止EUV曝光(波長13.5nm)時不宜曝光光、例如上述UV或DUV(ArF光、KrF光)之由基板或界面的反射的EUV阻劑的底層防反射膜,可使用上述阻劑底層膜形成組成物。在EUV阻劑的底層可有效率地防止反射。用作為EUV阻劑底層膜之場合,製程可與光阻用底層膜同樣進行。
以下、將本發明以實施例進一步具體說明,但不因此限定本發明。
在具備磁攪拌器的500ml四口燒瓶中,加入24.50g
之2-羥基乙基甲基碸、26.20g之溴化烯丙酯、29.96g之碳酸鉀、192g之丙酮,迴流條件下、進行12小時攪拌。使丙酮減壓餾去後,以70g之乙酸乙酯稀釋、以50g之純水進行2次洗淨。使有機相進行濃縮乾燥,得到化合物1 14.00g(收率:43%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:3.01ppm(s、3H)、3.23ppm(t、J=5.3Hz、2H)、3.89ppm(t、J=5.3Hz、2H)、4.03ppm(dt、J=5.7Hz、1.6Hz、2H)、5.23ppm(dq、J=10.4Hz、1.6HZ、1H)、5.29ppm(dq、J=17.2Hz、1.6Hz、1H)、5.88ppm(ddt、J=17.2Hz、10.4Hz、5.7Hz、1H)。
在具備磁攪拌器的200ml四口燒瓶中,加入12.40g之化合物1、與72g之甲苯,加入Karstedt觸媒(白金(0)-1,3-二乙烯-1,1,3,3-四甲基二矽氧烷錯合物0.1M二甲苯溶液)750μl、三乙氧基矽烷16.5ml。之後、在室溫進行24小時攪拌。使反應液濃縮乾燥後、減壓蒸餾(外溫:180℃~205℃、壓力:1torr)進行精製,得到化合物2 9.90g(收率:59%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:0.60ppm~
0.65ppm(m、2H)、1.23ppm(t、J=7.1Hz、9H)、1.65ppm~1.74ppm(m、2H)、3.00ppm(s、3H)、3.21ppm(t、J=5.3Hz、2H)、3.46ppm(t、J=6.9Hz、2H)、3.82ppm(q、J=7.1Hz、6H)、3.86ppm(t、J=5.3Hz、2H)。
在具備磁攪拌器的50ml四口燒瓶中,加入5.03g之苯基乙烯碸、7.13g之(3-巰基丙基)三乙氧基矽烷、0.30g之三乙基胺、30g之1,2-二氯乙烷,在室溫進行29小時攪拌。使反應液濃縮.乾燥,得到化合物3 11.84g(收率:97%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:0.66ppm~0.71ppm(m、2H)、1.22ppm(t、J=7.0Hz、9H)、1.60ppm~1.70ppm(m、2H)、2.51ppm(t、J=7.2Hz、2H)、2.76ppm~2.82ppm(m、2H)、3.30ppm~3.35ppm(m、2H)、3.81ppm(q、J=7.0Hz、6H)、7.56ppm~7.62ppm(m、2H)、7.68ppm(tt、J=7.4Hz、1.2Hz、1H)、7.89ppm~7.94ppm(m、2H)。
在具備磁攪拌器的100ml四口燒瓶中,加入1.50g之氫化鈉(純度:55%品)、5g之脫水THF(四氫呋喃),冰冷下,滴下2.48g之β-甲基烯丙基醇溶於10g之脫水THF之溶液。接著,滴下4-氟苯基甲基碸溶於30g之脫水THF的溶液。之後、室溫進行20小時攪拌。反應液以100g之乙酸乙酯稀釋後、以100g之純水進行2次、以50g之飽和食鹽水進行1次洗淨。使有機相進行濃縮乾燥,得到化合物4 6.50g(收率:100%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:1.84ppm(s、3H)、3.03ppm(s、3H)、4.51ppm(s、2H)、5.04ppm~5.10ppm(m、2H)、7.03ppm(d、J=9.2Hz、2H)、7.85ppm(d、J=9.2Hz、2H)。
在具備磁攪拌器的100ml四口燒瓶中,加入6.50g之化合物4、39g之甲苯,加入Karstedt觸媒(白金(0)-1,3-二乙烯-1,1,3,3-四甲基二矽氧烷錯合物0.1M二甲苯溶液)1450μl、三乙氧基矽烷13.6ml。之後、在50℃進行9小時攪拌。使反應液濃縮乾燥後、減壓蒸餾(外溫:200℃~245℃、壓力:1torr)進行精製,得到化合物5 3.03g(收率:27%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:0.62ppm(dd、J=15.3Hz、8.2Hz、1H)、0.86ppm(dd、J=15.3Hz、5.9Hz、1H)、1.12ppm(d、J=6.7Hz、3H)、1.22ppm(t、J=7.0Hz、9H)、2.16ppm~2.28ppm(m、1H)、3.03ppm(s、3H)、3.78ppm(dd、J=9.0Hz、7.0Hz、1H)、3.82ppm(q、J=7.0Hz、6H)、3.93ppm(dd、J=9.2Hz、5.7Hz、1H)、7.02ppm(d、J=9.0Hz、2H)、7.84ppm(d、J=9.0Hz、2H)。
在具備磁攪拌器的50ml四口燒瓶中,加入4.00g之4-(氯甲基)三甲氧基矽烷基苯、2.89g之p-甲苯亞磺酸鈉、16g之乙腈、16g之DMF(二甲基甲醯胺),60℃進行7小時攪拌。反應液以100g之乙酸乙酯稀釋後、以35g
之純水進行2次洗淨。進一步,使有機相以硫酸鈉脫水處理後、濃縮乾燥,得到化合物6 5.79g(收率:97%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:2.41ppm(s、3H)、3.61ppm(s、9H)、4.30ppm(s、2H)、7.13ppm(d、J=8.4Hz、2H)、7.23ppm(d、J=8.4Hz、2H)、7.50ppm(d、J=8.4Hz、2H)、7.55ppm(d、J=8.4Hz、2H)。
在具備磁攪拌器的200ml四口燒瓶中,加入10.00g之4-(氯甲基)苯乙烯、12.26g之p-甲苯亞磺酸鈉、40g之DMF,在60℃進行3小時攪拌。將反應液加入至320g之純水,過濾析出的結晶。使該結晶以48g之2-丙醇洗淨後、過濾乾燥,得到化合物7 15.39g(收率:86%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:2.42ppm(s、3H)、4.28ppm(s、2H)、5.28ppm(d、J=11.0Hz、1H)、5.75ppm(d、J=17.6Hz、1H)、6.68ppm(dd、J=17.6Hz、11.0Hz、1H)、7.04ppm(d、J=8.0Hz、2H)、7.24ppm(d、J=8.0Hz、2H)、7.30ppm
(d、J=8.0Hz、2H)、7.52ppm(d、J=8.0Hz、2H)。
在具備磁攪拌器的200ml四口燒瓶中,加入8.00g之化合物7、與64g之甲苯,加入Karstedt觸媒(白金(0)-1,3-二乙烯-1,1,3,3-四甲基二矽氧烷錯合物0.1M二甲苯溶液)1780μl、三乙氧基矽烷12.1ml。之後、在80℃進行13小時攪拌。使反應液濃縮乾燥後、減壓蒸餾(外溫:260℃、壓力:0.8torr)進行精製,得到化合物8 4.81g(收率:37%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:0.95ppm(m、2H)、1.23ppm(t、J=7.1Hz、9H)、2.43ppm(s、3H)、2.68ppm~2.73ppm(m、2H)、3.83ppm(q、J=7.1Hz、6H)、4.25ppm(s、2H)、7.00ppm(d、J=8.0Hz、2H)、7.11ppm(d、J=8.0Hz、2H)、7.24ppm(d、J=8.0Hz、2H)、7.52ppm(s、J=8.0Hz、2H)。
在具備磁攪拌器的100ml四口燒瓶中,加入10.00g之4-(氯甲基)三甲氧基矽烷基苯、4.55g之甲烷亞磺酸鈉、40g之DMF,在50℃進行4小時攪拌。使反應液以113g之乙酸乙酯稀釋後、以60g之純水進行5次洗淨。進一步,使有機相以硫酸鈉脫水處理後、濃縮乾燥,得到化合物9 9.61g(收率:82%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:2.77ppm(s、3H)、3.64ppm(s、9H)、4.27ppm(s、2H)、7.44ppm(d、J=8.0Hz、2H)、7.69ppm(d、J=8.0Hz、2H)。
在具備磁攪拌器的100ml四口燒瓶中,加入6.93g之4-(氯甲基)三甲氧基矽烷基苯、5.13g之4-氟苯亞磺酸
鈉、20g之DMF,在50℃進行2小時攪拌。使反應液以乙酸乙酯200ml稀釋後、以純水100ml進行5次洗淨。進一步,使有機相以硫酸鈉脫水處理後、濃縮乾燥,得到化合物10(9.78g)(收率:94%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:3.62ppm(s、9H)、4.32ppm(s、2H)、7.07ppm~7.15ppm(m、4H)、7.56ppm(d、J=8.2Hz、2H)、7.60ppm~7.65ppm(m、2H)。
在具備磁攪拌器的500ml四口燒瓶中,加入20.10g之4-(三氟甲基硫基)酚、72.85g之過碘酸鈉、120g之1,2-二氯乙烷、60g之乙腈、60g之純水,冰冷下,加入1.06g之氯化釕(III)。之後、在室溫進行22小時攪拌。使反應液以乙酸乙酯500g稀釋後、使鹽進行減壓吸引過濾,使濾液以300g之純水進行2次洗淨。使有機相以20g之硫酸鈉脫水後、濃縮乾燥,得到19.97g之化合物11(收率:85%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:7.07ppm(d、J=8.8Hz、2H)、7.92ppm(d、J=8.8Hz、2H)
在具備磁攪拌器的500ml四口燒瓶中,加入19.97g之化合物11、16.02g之溴化烯丙酯、24.48g之碳酸鉀、40g之DMF,在50℃進行2小時攪拌。使反應液以500g之乙酸乙酯稀釋後,使鹽進行減壓吸引過濾,使濾液以200g之純水進行3次、以100g之飽和食鹽水進行1次洗淨。使有機相濃縮乾燥,得到18.65g之化合物12的粗生成物。對該粗生成物16.00g,以減壓蒸餾(溫度:125~165℃、壓力:1torr)進行精製,得到6.28g之化合物12(收率:27%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:4.67ppm(dt、J=5.3Hz、1.6Hz、2H)、5.37ppm(dq、J=10.6Hz、1.6Hz、1H)、5.45ppm(dq、J=17.2Hz、1.6Hz、1H)、6.04ppm(ddt、J=17.2Hz、10.6Hz、5.3Hz、1H)、7.12ppm(d、J=9.0Hz、2H)、7.94ppm(d、J=9.0Hz、2H)
在具備磁攪拌器的100ml四口燒瓶中,加入6.11g之化合物12、37g之甲苯,加入340μl之Karstedt觸媒(白金(0)-1,3-二乙烯-1,1,3,3-四甲基二矽氧烷錯合物0.1M二甲苯溶液)、4.52g之三乙氧基矽烷。之後、在40℃進行5小時攪拌。使反應液濃縮乾燥後、減壓蒸餾(外溫:175~200℃、壓力:1torr)進行精製,得到1.06g之化合物13(收率:11%)。
1H-NMR(400MHz)、CDCl3溶劑中測定:0.75~0.80ppm(m、2H)、1.23ppm(t、J=7.1Hz、9H)、1.91~2.00ppm(m、2H)、3.83ppm(q、J=7.1Hz、6H)、4.08ppm(t、J=6.7Hz、2H)、7.08ppm(d、J=8.8Hz、2H)、7.93ppm(d、J=8.8Hz、2H)
將三乙氧基(3-(2-(苯基磺醯基)乙基硫基)丙基)矽烷(化合物3)3.43g(5mol%)、四乙氧基矽烷24.57g(70mol%)、甲基三乙氧基矽烷7.51g(25mol%)、丙酮53.26g加入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.24g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-1),GPC之重量平均分子量以聚苯乙烯換算為Mw1500。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.32g(5mol%)、三乙氧基(3-(2-(苯基磺醯基)乙基硫基)丙基)矽烷(化合物3)3.26g(5mol%)、四乙氧基矽烷23.41g(70mol%)、甲基三乙氧基矽烷5.72g(20mol%)、丙酮53.58g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸10.70g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加
溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-2),GPC之重量平均分子量以聚苯乙烯換算為Mw1500。
將三乙氧基(2-甲基-3-(4-(甲基磺醯基)苯氧基)丙基)矽烷(化合物5)3.30g(5mol%)、四乙氧基矽烷24.65g(70mol%)、甲基三乙氧基矽烷7.54g(25mol%)、丙酮53.24g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.27g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得
到的聚合物相當式(A-3),GPC之重量平均分子量以聚苯乙烯換算為Mw1500。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.33g(5mol%)、三乙氧基(2-甲基-3-(4-(甲基磺醯基)苯氧基)丙基)矽烷(化合物5)3.15g(5mol%)、四乙氧基矽烷23.49g(70mol%)、甲基三乙氧基矽烷5.74g(20mol%)、丙酮53.56g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸10.74g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-4),GPC之重量平均分子量以聚苯乙烯換算為Mw2200。
將三甲氧基(4-(甲苯磺醯基甲基)苯基)矽烷(化合物6)3.11g(5mol%)、四乙氧基矽烷24.78g(70mol
%)、甲基三乙氧基矽烷7.57g(25mol%)、丙酮53.20g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.33g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-5),GPC之重量平均分子量以聚苯乙烯換算為Mw1900。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.35g(5mol%)、三甲氧基(4-(甲苯磺醯基甲基)苯基)矽烷(化合物6)2.97g(5mol%)、四乙氧基矽烷23.60g(70mol%)、甲基三乙氧基矽烷5.77g(20mol%)、丙酮53.53g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸10.79g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副
產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-6),GPC之重量平均分子量以聚苯乙烯換算為Mw1500。
將三乙氧基(4-(甲苯磺醯基甲基)苯乙基)矽烷(化合物8)3.66g(5mol%)、四乙氧基矽烷24.42g(70mol%)、甲基三乙氧基矽烷7.46g(25mol%)、丙酮53.30g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.16g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-7),GPC之重量平均分子量以聚苯乙烯換算為Mw1400。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.30g(5mol%)、三乙氧基(4-(甲苯磺醯基(tosyl)甲基)苯乙基)矽烷(化合物8)3.48g(5mol%)、四乙氧基矽烷23.27g(70mol%)甲基三乙氧基矽烷5.69g(20mol%)、丙酮53.62g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸10.64g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-8),GPC之重量平均分子量以聚苯乙烯換算為Mw1500。
將4-(甲基磺醯基甲基)苯基三甲氧基矽烷(化合物9)2.51g(5mol%)、四乙氧基矽烷25.19g(70mol%)、甲基三乙氧基矽烷7.70g(25mol%)、丙酮53.09g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將
0.01mol/L之鹽酸11.52g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-9),GPC之重量平均分子量以聚苯乙烯換算為Mw3000。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.40g(5mol%)、4-(甲基磺醯基甲基)苯基三甲氧基矽烷(化合物9)2.39g(5mol%)、四乙氧基矽烷23.97g(70mol%)、甲基三乙氧基矽烷5.86g(20mol%)、丙酮53.42g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸10.96g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加
入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-10),GPC之重量平均分子量以聚苯乙烯換算為Mw2500。
將4-((p-氟苯基磺醯基)甲基)苯基三甲氧基矽烷(化合物10)3.14g(5mol%)、四乙氧基矽烷24.76g(70mol%)、甲基三乙氧基矽烷7.57g(25mol%)、丙酮53.21g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.32g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-11),GPC之重量平均分子量以聚苯乙烯換算為Mw2400。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.34g(5mol%)、4-((p-氟苯基磺醯基)甲基)苯基三甲氧基矽烷(化合物10)3.00g(5mol%)、四乙氧基矽烷23.58g(70mol%)、甲基三乙氧基矽烷5.77g(20mol%)、丙酮53.53g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸10.78g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-12),GPC之重量平均分子量以聚苯乙烯換算為Mw2000。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.30g(5mol%)、4-(甲基磺醯基甲基)苯基三甲氧基矽烷(化合物9)2.32g(5mol%)、四乙氧基矽烷24.94g(75mol%)、甲基三乙氧基矽烷2.85g(10mol%)、(4-(1-乙氧基乙氧基)苯基)三甲氧基矽烷2.29g(5mol%)、丙酮53.53g放入300mL之燒瓶,邊使混合
溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸10.79g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-13),GPC之重量平均分子量以聚苯乙烯換算為Mw2500。
將4-(甲基磺醯基甲基)苯基三甲氧基矽烷(化合物9)2.43g(5mol%)、四乙氧基矽烷26.17g(75mol%)、甲基三乙氧基矽烷4.48g(15mol%)、(4-(1-乙氧基乙氧基)苯基)三甲氧基矽烷2.40g(5mol%)、丙酮53.21g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.32g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加
入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-14),GPC之重量平均分子量以聚苯乙烯換算為Mw2500。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.30g(5mol%)、4-(甲基磺醯基甲基)苯基三甲氧基矽烷(化合物9)2.31g(5mol%)、四乙氧基矽烷24.91g(75mol%)、甲基三乙氧基矽烷2.76g(9.7mol%)、(4-(1-乙氧基乙氧基)苯基)三甲氧基矽烷2.28g(5mol%)、N-(3-三乙氧基矽烷基丙基)-4,5-二氫咪唑0.13g(0.3mol%)、丙酮53.54g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.10mol/L之鹽酸10.79g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單乙基醚72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單乙基醚溶液。進行稀釋,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-15),GPC之重量平均分子量以聚苯乙烯換算為Mw2500。
將4-(甲基磺醯基甲基)苯基三甲氧基矽烷(化合物9)2.43g(5mol%)、四乙氧基矽烷26.13g(75mol%)、甲基三乙氧基矽烷4.38g(14.7mol%)、(4-(1-乙氧基乙氧基)苯基)三甲氧基矽烷2.40g(5mol%)、N-(3-三乙氧基矽烷基丙基)-4,5-二氫咪唑0.14g(0.3mol%)、丙酮53.22g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.10mol/L之鹽酸11.32g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單乙基醚72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單乙基醚溶液。進行稀釋,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-16),GPC之重量平均分子量以聚苯乙烯換算為Mw2500。
將3.44g(5mol%)之(3-(4-((三氟甲基)磺醯基)苯氧基)丙基)三乙氧基矽烷(化合物13)、23.30g(70mol%)之四乙氧基矽烷、5.70g(20mol%)之甲基三乙氧基矽烷、3.30g(5mol%)之3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯、53.61g之丙酮放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之
鹽酸10.66g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之甲醇、乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(A-17),GPC之重量平均分子量以聚苯乙烯換算為Mw1500。
將3-(三乙氧基矽烷基丙基)二烯丙基異氰脲酸酯3.48g(5mol%)、四乙氧基矽烷24.53g(70mol%)、甲基三乙氧基矽烷7.50g(25mol%)、丙酮53.27g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.22g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯
/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(B-1),GPC之重量平均分子量以聚苯乙烯換算為Mw1800。
將3-三乙氧基矽烷基丙氧基甲基乙基碸(化合物2)2.81g(5mol%)、四乙氧基矽烷24.98g(70mol%)、甲基三乙氧基矽烷7.64g(25mol%)、丙酮53.15g放入300mL之燒瓶,邊使混合溶液以磁攪拌器攪拌邊將0.01mol/L之鹽酸11.42g滴下至混合溶液。添加後、使燒瓶移至調整為85℃的油浴,在加溫迴流下進行240分鐘反應。之後、使反應溶液冷卻至室溫,於反應溶液中加入丙二醇單甲基醚乙酸酯72.00g,使反應副產物之乙醇、水、鹽酸、丙酮減壓餾去,並進行濃縮而得到水解縮合物(聚合物)丙二醇單甲基醚乙酸酯溶液。加入丙二醇單甲基醚乙酸酯以及丙二醇單乙基醚,作為丙二醇單甲基醚乙酸酯/丙二醇單乙基醚20/80的溶劑比率,以140℃之固形殘物換算成為15重量%之方式進行調整。得到的聚合物相當式(B-2),GPC之重量平均分子量以聚苯乙烯換算為
Mw1600。
使上述合成例1~合成例17及比較合成例1及比較合成例2得到的含矽聚合物、酸、硬化觸媒、添加劑、溶劑、水如表1所示比例之方式混合,藉由以0.1μm的氟樹脂製的過濾器進行過濾,各自調製阻劑底層膜形成組成物的溶液。表1中之聚合物的添加比例非以聚合物溶液的質量,而表示聚合物本身的質量。
表1中,各自之縮寫如下,馬來酸為MA、氯化三乙基苄基銨為BTEAC、N-(3-三乙氧基矽烷基丙基)-4,5-二氫咪唑為IMIDTEOS、三苯基鋶三氟甲烷磺酸酯為TPS105、馬來酸單三苯基鋶為TPSMA、三苯基鋶樟腦磺酸酯為TPSCS、丙二醇單甲基醚乙酸酯為PGMEA、丙二醇單乙基醚為PGEE、丙二醇單甲基醚為PGME。水使用超純水。各添加量以質量份表示。
氮下、在100mL四口燒瓶中,加入咔唑(6.69g、0.040mol、東京化成工業(股)製)、9-芴酮(7.28g、0.040mol、東京化成工業(股)製)、對甲苯磺酸一水合物(0.76g、0.0040mol、東京化成工業(股)製),加入1,4-二噁烷(6.69g、關東化學(股)製)並進行攪拌,升溫至100℃、使溶解,開始聚合。24小時後放冷至60℃後,加入氯仿(34g、關東化學(股)製)並稀釋,至甲醇(168g、關東化學(股)製)中使再沈澱。將得到的沈澱物過濾,以減壓乾燥機在80℃、進行24小時乾燥,得到目的聚合物(式(C-1)、以下簡稱PCzFL)9.37g。
PCzFL之1H-NMR的測定結果如下。
1H-NMR(400MHz,DMSO-d6):δ 7.03-7.55(br、12H)、δ 7.61-8.10(br、4H)、δ 11.18(br、1H)。
PCzFL之GPC之聚苯乙烯換算所測定的重量平均分子量MW為2800、多分散度Mw/Mn為1.77。
在得到的樹脂20g中,混合作為交聯劑的四甲氧基甲基乙炔脲(Mitsui-Cytec(股)製、商品名Powderlink 1174)3.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.30g、作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶於丙二醇單甲基醚乙酸酯88g作
成溶液。之後、使用孔徑0.10μm的聚乙烯製微過濾器進行過濾,進一步,使用孔徑0.05μm的聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程所使用的有機底層膜(A層)形成組成物的溶液。
將實施例1~實施例24、比較例1及比較例2所調製的含Si阻劑底層膜形成組成物使用旋轉器,各自在矽晶圓上塗佈。在加熱板上以200℃進行1分鐘加熱,形成含Si阻劑底層膜(膜厚0.05μm)。接著,使此等之阻劑底層膜以分光橢圓測厚儀(J.A.Woollam公司製、VUV-VASE VU-302),測定在波長193nm之折射率(n值)及光學吸光係數(k值、亦稱衰減係數)。
乾蝕刻速度的測定使用的蝕刻機台及蝕刻氣體係使用以下者。
ES401(Nippon Scientific Co.,Ltd.製):CF4
RIE-10NR(Samco製):O2
將實施例1~實施例24、比較例1及比較例2所調製的含Si阻劑底層膜形成組成物的溶液使用旋轉器,在矽晶圓上塗佈。在加熱板上以240℃進行1分鐘加熱,各自形成含Si阻劑底層膜(膜厚0.08μm(CF4氣體之蝕刻速度測定用)、0.05μm(O2氣體之蝕刻速度測定用)。又,
同樣地將有機底層膜形成組成物使用旋轉器,在矽晶圓上形成塗膜(膜厚0.20μm)。作為蝕刻氣體使用O2氣體,測定乾蝕刻速度,進行實施例1~比較例20、以及比較例1及比較例2的含Si阻劑底層膜的乾蝕刻速度的比較。
將上述式得到的有機底層膜(A層)形成組成物塗佈於矽晶圓上,在加熱板上以240℃進行60秒鐘烘烤,得到膜厚200nm的有機底層膜(A層)。於其上塗佈實施例1~實施例24、以及比較例1及比較例2得到的含Si阻劑底層膜(B層)形成組成物,在加熱板上以240℃進行45秒鐘烘烤,得到含Si阻劑底層膜(B層)。含Si阻劑底層膜(B層)之膜厚為45nm。
於其上,將市售的光阻溶液(JSR(股)製、商品名AR2772)藉由旋轉器各自進行塗佈,在加熱板上以110℃進行60秒鐘烘烤,形成膜厚120nm的光阻膜(C層)。阻劑的圖型化使用NIKON公司製ArF曝光機S-307E(波長193nm、NA、σ:0.85、0.93/0.85(Dipole)液浸液:水)進行。標靶透過顯影後光阻的線寬以及其線間的寬為0.065μm、亦即以形成線與間隔(稠密線)之方式設定的遮罩進行曝光。
之後、在加熱板上以110℃進行60秒鐘烘烤,冷卻後以60秒單槳式步驟以2.38質量%濃度的四甲基氫氧化銨水溶液(顯影液)進行顯影。進行微影術後之阻劑圖型下
擺形狀中線為矩形者為直條,線底部變寬為腳化。
表2在193nm波長的折射率n、在193nm波長的光學吸收係數k、氟系氣體(CF4氣體)之蝕刻速度(etch rate:nm/分鐘)、氧系氣體(O2氣體)耐性以〔本發明阻劑底層膜(B層)〕/〔有機底層膜(A層)〕之蝕刻速度比表示。又,觀察微影術評估後之阻劑下擺形狀並表示其結果。
使上述式得到的有機底層膜(A層)形成組成物塗佈於矽晶圓上,在加熱板上以240℃進行60秒鐘烘烤,得到膜厚200nm的有機底層膜(A層)。於其上,塗佈本發明阻劑底層膜形成組成物,並在加熱板上以240℃進行1分
鐘加熱,形成膜厚35nm的阻劑的底層膜(B層)。於其上將市售的光阻溶液(富士軟片(股)製、商品名FAiRS-9521NT05)以旋轉器各自塗佈,並在加熱板上以100℃進行1分鐘加熱,形成膜厚85nm的光阻膜(C層)。
接著、使用(股)nikon製NSR-S307E掃描儀(波長193nm、NA、σ:0.85、0.93/0.85),顯影後透過光阻的線寬及其線間的寬為0.065μm、亦即設定為形成0.065μm的線與間隔(L/S)=1/1之稠密線的遮罩進行曝光。之後、在加熱板上100℃進行60秒鐘烘烤,冷卻後,使用乙酸丁酯(溶劑顯影液)進行60秒顯影,於阻劑底層膜(B層)上形成負型之圖型。
關於得到的光阻圖型,不產生大的圖型剝離或底切者評估為良好,記載於表3。
可利用作為形成可用作為硬遮罩的阻劑底層膜用之微影術用阻劑底層膜形成組成物。接著,不與上塗阻劑產生互混。在氟系之蝕刻氣體與阻劑比較具有大的乾蝕刻速度,可使阻劑圖型轉印在本發明阻劑底層膜,且對氧系蝕刻氣體具有蝕刻耐性,可於有機底層膜轉印阻劑圖型。如此可提供形成矩形圖型且可進行基板加工之阻劑底層膜用之阻劑底層膜形成組成物。
Claims (9)
- 一種微影術用阻劑底層膜形成組成物,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,且該水解性有機矽烷為式(3):R1 aSi(R2)4-a 式(3)(式(3)中,R1為烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、或彼等之組合,且藉由Si-C鍵結與矽原子鍵結者,R2為烷氧基、醯基氧基或鹵素基,a為0~3之整數)、及式(4):〔R1 cSi(R2)3-c〕2Yb 式(4)(式(4)中,R1為烷基,R2為烷氧基、醯基氧基或鹵素基,Y為伸烷基或伸芳基,b為0或1之整數,c為0或1之整數)所成群中選出的至少1種之有機矽化合物、與式(1)所表示的水解性有機矽烷之組合,〔(R1)aSi(R2)(3-a)〕b(R3) 式(1)〔式(1)中,R3為下述式(2):(式(2)中,R4、Ar1、R5、Ar2、及R6之基中1個~3個的基為以Si-C鍵結與Si原子鍵結者,R4為可具有硫鍵或醚鍵的1價~4價之烴基,R5為可具有硫鍵或醚鍵的2價~4價之烴基,R6為可經取代的1價~4價之烴基,Ar1及Ar2各自為可經取代的碳原子數6~20的伸芳基或芳基,n2為1之整數,n1、n3、n4、及n5各自為0或1之整數,n4與n5為不同時為0之整數)所表示的基,R1為烷基、芳基、芳烷基、鹵素化烷基、鹵素化芳基、鹵素化芳烷基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、烷氧基芳基、醯基氧基芳基、異氰脲酸酯基、羥基、環狀胺基、或者氰基的有機基、或彼等之組合,且以Si-C鍵結與Si原子鍵結的有機基,R2為烷氧基、醯基氧基、或鹵素基,a為0~2之整數,b為1~3之整數〕。
- 如請求項1記載之阻劑底層膜形成組成物,其係含有上述式(1)所表示的化合物的水解縮合物、或上述式(1)所表示的化合物與式(3)所表示的化合物之水解縮合物作為聚合物。
- 如請求項1或2記載之阻劑底層膜形成組成物,其中,再含有酸。
- 如請求項1或2記載之阻劑底層膜形成組成物,其中,再含有水。
- 如請求項1或2記載之阻劑底層膜形成組成物,其中,再含有銨化合物、環狀銨化合物、環狀胺化合物、或鋶化合物。
- 一種阻劑底層膜,其特徵係藉由將請求項1~請求項5中任1項記載之阻劑底層膜形成組成物塗佈於半導體基板上並進行燒成而得到。
- 一種半導體裝置的製造方法,其特徵係包含將請求項1~請求項5中任1項記載之阻劑底層膜形成組成物塗佈於半導體基板上、進行燒成而形成阻劑底層膜之步驟、在前述阻劑底層膜上塗佈阻劑用組成物並形成阻劑膜之步驟、使前述阻劑膜曝光之步驟、曝光後將前述阻劑膜顯影而得到阻劑圖型之步驟、藉由該阻劑圖型將前述阻劑底層膜蝕刻之步驟、及藉由經圖型化的前述阻劑膜與前述阻劑底層膜將前述半導體基板加工之步驟。
- 一種半導體裝置的製造方法,其特徵係含有在半導體基板上形成有機底層膜之步驟、於其上塗佈請求項1~請求項5中任1項記載之阻劑底層膜形成組成物並燒成而形成阻劑底層膜之步驟、在前述阻劑底層膜上塗佈阻劑用組成物並形成阻劑膜之步驟、使前述阻劑膜曝光之步驟、曝光後將前述阻劑膜顯影而得到阻劑圖型之步驟、藉由前述阻劑圖型使前述阻劑底層膜進行蝕刻之步驟、藉由經圖型化的前述阻劑底層膜將前述有機底層膜蝕刻之步驟、及藉由經圖型化的前述有機底層膜將前述半導體基板加工之步驟。
- 一種由以下化合物選出之化合物,
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CN103748517A (zh) | 2014-04-23 |
JP6150088B2 (ja) | 2017-06-21 |
KR20140045962A (ko) | 2014-04-17 |
JPWO2013022099A1 (ja) | 2015-03-05 |
KR101947103B1 (ko) | 2019-02-13 |
US20140170855A1 (en) | 2014-06-19 |
JP2016179982A (ja) | 2016-10-13 |
WO2013022099A1 (ja) | 2013-02-14 |
CN103748517B (zh) | 2017-04-19 |
TW201319751A (zh) | 2013-05-16 |
JP5999373B2 (ja) | 2016-09-28 |
US9524871B2 (en) | 2016-12-20 |
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