TW201512304A - 含有吡咯酚醛清漆樹脂之光阻下層膜形成組成物 - Google Patents
含有吡咯酚醛清漆樹脂之光阻下層膜形成組成物 Download PDFInfo
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- TW201512304A TW201512304A TW103121880A TW103121880A TW201512304A TW 201512304 A TW201512304 A TW 201512304A TW 103121880 A TW103121880 A TW 103121880A TW 103121880 A TW103121880 A TW 103121880A TW 201512304 A TW201512304 A TW 201512304A
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- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
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- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-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
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Classifications
-
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Abstract
本發明之課題係可提供一種優異的光阻下層膜,其具有:接近光阻之乾蝕刻速度之選擇比、較光阻小之乾蝕刻速度之選擇比或較半導體基板小之乾蝕刻速度之選擇比。
解決課題之手段為一種光阻下層膜形成組成物,其包含含有下述式(1)之單位構造之聚合物:
□
(式(1)中,R3為氫原子、或可經鹵基、硝基、胺基、羰
基、碳數6~40之芳基、或羥基所取代的碳數6~40之芳基、或雜環基;R4為氫原子、或可經鹵基、硝基、胺基、或羥基所取代的碳數1~10之烷基、碳數6~40之芳基、或雜環基;R3及R4可與此等所鍵結之碳原子一起形成環;n表示0至2之整數)。式(1)的R3為苯環、萘環、蒽環或芘環,R4為氫原子。
Description
本發明係關於半導體基板加工時為有效之微影用光阻下層膜形成組成物、及使用該光阻下層膜形成組成物之光阻圖型形成法、及半導體裝置之製造方法。
以往以來在半導體裝置之製造中,係藉由使用光阻組成物之微影來進行微細加工。前述微細加工係於矽晶圓等的被加工基板上形成光阻組成物之薄膜,再於其上方以隔著描繪有半導體裝置之圖型的遮罩圖型來照射紫外線等的活性光線,顯影後,將所得到的光阻圖型作為保護膜,來蝕刻處理矽晶圓等的被加工基板之加工法。然而,近年來,隨著半導體裝置之高積體化進展,使用之活性光線亦有自KrF準分子雷射(波長248nm)朝ArF準分子雷射(波長193nm)短波長化之傾向。伴隨於此,活性光線之自基板之亂反射或駐波之影響成為大的問題。因而廣泛檢討於光阻與被加工基板間設置防反射膜(底部抗反射圖
層,Bottom Anti-Reflective Coating:BARC)之方法。
今後,光阻圖型朝微細化進行時,由於會產生所謂解析度之問題或光阻圖型在顯像後崩塌之問題,故期望光阻之薄膜化。因而,於基板加工時難以獲得充分之光阻圖型膜厚,不僅光阻圖型,在光阻與經加工半導體基板之間所形成之光阻下層膜亦變得必須具有作為基板加工時之遮罩之功能之製程。與作為如此般製程使用之光阻下層膜之以往之高蝕刻速率性(蝕刻速度快速)光阻下層膜不同,要求具有與光阻接近之乾蝕刻速度之選擇比之微影用光阻下層膜、具有較光阻小之乾蝕刻速度之選擇比之微影用光阻下層膜、或具有較半導體基板小之乾蝕刻速度之選擇比之微影用光阻下層膜。
作為上述光阻下層膜用之聚合物,有揭示例如以下者。揭示著使用咔唑酚醛清漆樹脂之光阻下層膜形成組成物(參考專利文獻1、專利文獻2、及專利文獻3)。
[專利文獻1]國際公開WO2010/147155說明書
[專利文獻2]國際公開WO2012/077640說明書
[專利文獻3]國際公開WO2013/005797說明書
本發明係提供為了使用於半導體裝置製造之微影製程之光阻下層膜形成組成物。又,本發明係提供不會引起與光阻層之相互混合(intermixing),而可得到優越的光阻圖型,且具有接近光阻之乾蝕刻速度之選擇比之微影用光阻下層膜、具有較光阻小之乾蝕刻速度之選擇比之微影用光阻下層膜、或具有較半導體基板小之乾蝕刻速度之選擇比之微影用光阻下層膜。又,本發明係將248nm、193nm、157nm等的波長之照射光使用於微細加工時,亦可賦予有效地吸收來自基板的反射光之性能。再者,本發明為提供使用光阻下層膜形成組成物之光阻圖型之形成法。又,提供為了形成兼具耐熱性之光阻下層膜之光阻下層膜形成組成物。
作為本發明之第1觀點為一種光阻下層膜形成組成物,其包含含有下述式(1)之單位構造之聚合物:
(式(1)中,R1為氫原子、碳數1~10之烷基、碳數2~10之烯基、碳數6~40之芳基、及選自由此等基之組合所成之群,此時,該烷基、該烯基、或該芳基可包含醚鍵、酮鍵、或酯鍵;R2為鹵基、硝基、胺基、羥基、碳數1~10之烷基、碳數2~10之烯基、及碳數6~40之芳基、及選自由此等基之組合所成之群,此時,該烷基、該烯基、或該芳基可包含醚鍵、酮鍵、或酯鍵;R3為氫原子、或可經鹵基、硝基、胺基、羰基、碳數6~40之芳基、或羥基所取代的碳數6~40之芳基、或雜環基;R4為氫原子、或可經鹵基、硝基、胺基、或羥基所取代的碳數1~10之烷基、碳數6~40之芳基、或雜環基;R3及R4可與此等所鍵結之碳原子一起形成環;n表示0至2之整數)。
作為第2觀點,如第1觀點之光阻下層膜形成組成物,其中,式(1)的R3為苯環、萘環、蒽環或芘環,R4為氫原子,n為0。
作為第3觀點,如第1觀點或第2觀點之光阻下層膜形成組成物,其中,進而包含交聯劑。
作為第4觀點,如第1觀點至第3觀點中任一項之光阻下層膜形成組成物,其中,進而包含酸及/或酸產生劑。
作為第5觀點為一種光阻下層膜,其係藉由將第1觀點至第4觀點中任一項之光阻下層膜形成組成物塗佈於半導體基板上並經燒成而得。
作為第6觀點為一種使用於半導體之製造之光阻圖型之形成方法,其係包含將第1觀點至第4觀點中任一項之光阻下層膜形成組成物塗佈於半導體基板上並經燒成而形成下層膜之步驟。
作為第7觀點為一種半導體裝置之製造方法,其係包含於半導體基板上,藉由第1觀點至第4觀點中任一項之光阻下層膜形成組成物形成下層膜之步驟、於其上方形成光阻膜之步驟、藉由光或電子線之照射與顯影形成光阻圖型之步驟、藉由光阻圖型蝕刻該下層膜之步驟、及利用已圖型化之下層膜來加工半導體基板之步驟。
作為第8觀點為一種半導體裝置之製造方法,其係包含於半導體基板上,藉由第1觀點至第4觀點中任一項之光阻下層膜形成組成物形成下層膜之步驟、於其上方形成硬遮罩之步驟、於其上方進而形成光阻膜之步驟、藉由光或電子線之照射與顯影形成光阻圖型之步驟、藉由光阻圖型蝕刻硬遮罩之步驟、利用已圖型化之硬遮罩來蝕刻該下
層膜之步驟、及利用已圖型化之下層膜來加工半導體基板之步驟。
作為第9觀點,如第8觀點之製造方法,其中,硬遮罩係藉由無機物的蒸鍍而得到者。
以及,作為第10觀點為一種聚合物,其係含有下述式(5)之單位構造:
(式(5)中,R21為氫原子、碳數1~10之烷基、碳數2~10之烯基、碳數6~40之芳基、及選自由此等基之組合所成之群,此時,該烷基、該烯基、或該芳基可包含醚鍵、酮鍵、或酯鍵;R22為鹵基、硝基、胺基、羥基、碳數1~10之烷基、碳數2~10之烯基、碳數6~40之芳基、及選自由此等基之組合所成之群,此時,該烷基、該烯基、或該芳基可包含醚鍵、酮鍵、或酯鍵;R23為氫原子、或可經鹵基、硝基、胺基、羰基、碳數6~40之芳基、或羥
基所取代的碳數6~40之芳基、或雜環基;R24為可經鹵基、硝基、胺基、或羥基所取代的碳數1~10之烷基、碳數6~40之芳基、或雜環基;R23及R24可與此等所鍵結之碳原子一起形成環;n表示0至2之整數)。
藉由本發明之光阻下層膜形成組成物,不會引起光阻下層膜之上層部與被覆於其上方之層之相互混合,可形成良好的光阻膜之圖型形狀。
本發明之光阻下層膜形成組成物,亦可能賦予有效率地抑制來自基板之反射之性能,可兼具作為曝光之光之防反射膜之效果。
藉由本發明之光阻下層膜形成組成物,可提供具有接近光阻之乾蝕刻速度之選擇比、較光阻小之乾蝕刻速度之選擇比或較半導體基板小之乾蝕刻速度之選擇比之優越的光阻下層膜。
為了防止伴隨著光阻圖型微細化而於顯像後光阻圖型倒塌之問題,因而進行光阻薄膜化。就如此般之薄膜光阻而言,可適用於:以蝕刻製程將光阻圖型轉印至該下層膜,再將該下層膜作為遮罩進行基板加工之製程;或重複進行以蝕刻製程將光阻圖型轉印至該下層膜,進而,再使用不同的氣體組成將轉印至下層膜之圖型轉印於該下層膜之步驟,最後進行基板加工之製程。本發明之光阻下層膜及其形成組成物,對此等之製程為有效,且使用
本發明之光阻下層膜加工基板時,對於加工基板(例如基板上的熱氧化矽膜、氮化矽膜、聚矽膜等)具有充分的耐蝕刻性。
又,本發明之光阻下層膜係可作為平坦化膜、光阻下層膜、光阻膜層之污染防止膜、具有乾蝕刻選擇性之膜使用。由此,可容易精度良好地進行於半導體製造之微影製程中之光阻圖型形成。
本發明可適用於下述製程:將由本發明之光阻下層膜形成組成物所成之光阻下層膜形成於基板上,於其上方形成硬遮罩,並於其上方形成光阻膜,藉由曝光與顯影形成光阻圖型,將光阻圖型轉印至硬遮罩,並將被轉印至硬遮罩之光阻圖型轉印至光阻下層膜,以該光阻下層膜進行半導體基板之加工之製程。於此製程之硬遮罩之形成,有藉由包含有機聚合物或無機聚合物、與溶劑之塗佈型之組成物進行之情形,及藉由無機物之真空蒸鍍進行之情形。就無機物(例如氮化氧化矽)之真空蒸鍍而言,雖然蒸鍍物會堆積在光阻下層膜表面,但此時光阻下層膜表面之溫度會上昇至400℃前後。本發明中所使用之聚合物為包含吡咯酚醛清漆系之單位構造之聚合物,故具有極高耐熱性,即使是堆積蒸鍍物也不會產生熱劣化。
本發明係包含含有式(1)之單位構造之聚合物
之光阻下層膜形成組成物。含有式(1)之單位構造之聚合物,其係藉由吡咯與醛或酮之反應所形成之酚醛清漆聚合物。
本發明中,上述微影用光阻下層膜形成組成物係包含上述聚合物與溶劑。又,可包含交聯劑與酸,亦可因應所需包含酸產生劑、界面活性劑等的添加劑。此組成物之固形分為0.1~70質量%、或0.1~60質量%。固形分係由光阻下層膜形成組成物中,除去溶劑外之全成分之含有比例。固形分中,可以1~100質量%、1~99.9質量%、50~99.9質量%、50~95質量%、或50~90質量%之比例含有上述聚合物。
本發明中所使用之聚合物,重量平均分子量為600~1000000、或600~200000。
式(1)中,R1為氫原子、碳數1~10之烷基、碳數2~10之烯基、碳數6~40之芳基、及選自由此等基之組合所成之群,此時,該烷基、該烯基、或該芳基可包含醚鍵、酮鍵、或酯鍵;R2為鹵基、硝基、胺基、羥基、碳數1~10之烷基、碳數2~10之烯基、碳數6~40之芳基、及選自由此等基之組合所成之群,此時,該烷基、該烯基、或該芳基可包含醚鍵、酮鍵、或酯鍵;R3為氫原子、或鹵基、硝基、胺基、羰基、碳數6~40之芳基、或可以羥基取代之碳數6~40之芳基、或雜環基;R4為氫原子、或鹵基、硝基、胺基、或可以羥基取代之碳數1~10之烷基、碳數6~40之芳基、或雜環基;R3及R4可與此
等所鍵結之碳原子一起形成環。作為此等之環,例如可以具有R3及R4分別鍵結於茀的9位之構造。n表示0至2之整數。
式(1)的R3可作為苯環、萘環、蒽環或芘環,R4可作為氫原子,n為0。
作為上述鹵基,可舉例氟原子、氯原子、溴原子、碘原子。
作為上述碳數6~40之芳基,若例如將碳數6~40之芳基作為苯基、可取代之碳數6~40之芳基作為苯基時,可舉例以苯基取代之苯基(即聯苯基)等。
作為上述碳數1~10之烷基,可舉例:甲基、乙基、n-丙基、i-丙基、環丙基、n-丁基、i-丁基、s-丁基、t-丁基、環丁基、1-甲基-環丙基、2-甲基-環丙基、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、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、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、1-乙基-2-甲基-n-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。
作為上述碳數2~10之烯基,可舉例: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-伸甲基-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-伸甲基-環戊基、1-環己烯基、2-環己烯基及3-環己烯基等。
作為上述碳數6~40之芳基,可舉例: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-氟苯基、o-甲氧基苯
基、p-甲氧基苯基、p-硝基苯基、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-菲基等。
作為上述雜環基,較佳為自含有氮、硫、氧之5~6員環的雜環所成之有機基,可舉例例如:吡咯基、呋喃基、噻吩基、咪唑基、噁唑基、噻唑基、吡唑基、異噁唑基、異噻唑基、吡啶基等。
作為使用於本發明之聚合物製造之醛類,可舉例:甲醛、三聚甲醛、乙醛、丙醛、丁醛、異丁醛、戊醛、己醛、2-甲基丁醛、己基醛、十一烷醛、7-甲氧基-3,7-二甲基辛基醛、環己烷醛、3-甲基-2-丁醛、乙二醛、丙二醛、丁二醛、戊二醛、己二醛、等的飽和脂肪族醛類、丙烯醛、甲基丙烯醛等的不飽和脂肪族醛類、糠醛、吡啶醛等的雜環式醛類、苯甲醛、萘醛、蒽醛、菲基醛、水楊基醛、苯基乙醛、3-苯基丙醛、甲苯甲醛、(N,N-二甲基胺基)苯甲醛、乙醯氧基苯甲醛等的芳香族醛類等。特佳為可使用芳香族醛。
又,本發明之聚合物之製造所使用之酮類為二芳基酮類,可舉例例如:二苯基酮、苯基萘基酮、二萘基酮、苯基甲苯基酮、二甲苯基酮、9-茀酮等。
本發明中所使用之聚合物係將吡咯與醛類或酮類進行縮合所得到的酚醛清漆樹脂。此縮合反應中,相對於吡咯1當量,可以0.1~10當量之比例來使用醛類或
酮類。
作為上述縮合反應所使用之酸觸媒,可使用例如:硫酸、磷酸、過氯酸等的鑛酸類、p-甲苯磺酸、p-甲苯磺酸一水合物等的有機磺酸類、甲酸、草酸等的羧酸類。酸觸媒之使用量可依所使用的酸類種類適當選擇。一般,相對於吡咯100質量份為0.001~10000質量份,較佳為0.01~1000質量份,又較佳為0.1~100質量份。
上述之縮合反應可於不使用溶劑下進行,但通常使用溶劑下進行。作為溶劑,只要是不阻礙反應者即可,全部皆可使用。可舉例例如四氫呋喃、二噁烷等的環狀醚類。又,所使用之酸觸媒例如為甲酸般之液狀物時,亦可兼具作為溶劑之功用。
縮合時之反應溫度一般為40℃~200℃。反應時間可依反應溫度作各種選擇,但一般為30分鐘~50小時左右。以上般之方式所得到的聚合體之重量平均分子量Mw一般為400~1000000、400~200000、400~50000、或600~10000。
含有式(1)之單位構造之聚合物可以例如以下例示。
上述聚合物在全部聚合物中可以30質量%以內混合其他聚合物而使用。作為此等聚合物,可舉例:聚丙烯酸酯化合物、聚甲基丙烯酸酯化合物、聚丙烯醯胺化合物、聚甲基丙烯醯胺化合物、聚乙烯化合物、聚苯乙烯化合物、聚馬來醯亞胺化合物、聚馬來酸酐、及聚丙烯腈化合物。
作為聚丙烯酸酯化合物之原料單體,可舉例:丙烯酸甲酯、丙烯酸乙酯、丙烯酸異丙酯、丙烯酸苄酯、丙烯酸萘酯、丙烯酸蒽酯、丙烯酸蒽基甲酯、丙烯酸苯酯、丙烯酸2-羥基乙酯、丙烯酸2-羥基丙酯、丙烯酸2,2,2-三氟乙酯、丙烯酸4-羥基丁酯、丙烯酸異丁酯、丙烯酸第三丁酯、丙烯酸環己酯、丙烯酸異冰片酯、丙烯酸2-甲氧基乙酯、丙烯酸甲氧基三乙二醇酯、丙烯酸2-乙氧基乙酯、丙烯酸四氫糠酯、丙烯酸3-甲氧基丁酯、丙烯酸2-甲基-2-金剛烷酯、丙烯酸2-乙基-2-金剛烷酯、丙烯酸2-丙基-2-金剛烷酯、丙烯酸2-甲氧基丁基-2-金剛烷酯、丙烯酸8-甲基-8-三環癸酯、丙烯酸8-乙基-8-三環癸酯及丙烯酸5-丙烯醯氧基-6-羥基降冰片烯-2-羧酸-6-內酯等。
作為聚甲基丙烯酸酯化合物之原料單體,可舉例:甲基丙烯酸乙酯、甲基丙烯酸正丙酯、甲基丙烯酸正戊酯、甲基丙烯酸環己酯、甲基丙烯酸苄酯、甲基丙烯酸萘酯、甲基丙烯酸蒽酯、甲基丙烯酸蒽基甲酯、甲基丙烯酸苯酯、甲基丙烯酸2-苯基乙酯、甲基丙烯酸2-羥基乙酯、甲基丙烯酸2-羥基丙酯、甲基丙烯酸2,2,2-三氟乙
酯、甲基丙烯酸2,2,2-三氯乙酯、丙烯酸甲酯(甲基丙烯酸甲酯)、甲基丙烯酸異丁酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸異癸酯、甲基丙烯酸正月桂酯、甲基丙烯酸正硬脂酯、甲基丙烯酸甲氧基二乙二醇酯、甲基丙烯酸甲氧基多乙二醇酯、甲基丙烯酸四氫糠酯、甲基丙烯酸異冰片酯、甲基丙烯酸第三丁酯、甲基丙烯酸異硬脂酯、甲基丙烯酸正丁氧基乙酯、甲基丙烯酸3-氯-2-羥基丙酯、甲基丙烯酸2-甲基-2-金剛烷酯、甲基丙烯酸2-乙基-2-金剛烷酯、甲基丙烯酸2-丙基-2-金剛烷酯、甲基丙烯酸2-甲氧基丁基-2-金剛烷酯、甲基丙烯酸8-甲基-8-三環癸酯、甲基丙烯酸8-乙基-8-三環癸酯、甲基丙烯酸5-甲基丙烯醯氧基-6-羥基降冰片烯-2-羧酸-6-內酯及甲基丙烯酸2,2,3,3,4,4,4-七氟丁基酯等。
作為聚丙烯醯胺化合物之原料單體,可舉例: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、及N,N-二甲基丙烯醯胺等。
作為聚甲基丙烯醯胺化合物之原料單體,可舉例: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、及N,N-二甲基甲基丙烯醯胺等。
作為聚乙烯化合物之原料單體,可舉例:乙烯醚、甲基乙烯醚、苄基乙烯醚、2-羥基乙基乙烯醚、苯基乙烯醚、及丙基乙烯醚等。
作為聚苯乙烯化合物之原料單體,可舉例:苯乙烯、甲基苯乙烯、氯苯乙烯、溴苯乙烯、及羥基苯乙烯等。
作為聚馬來醯亞胺化合物之原料單體,可舉例:馬來醯亞胺、N-甲基馬來醯亞胺、N-苯基馬來醯亞胺、及N-環己基馬來醯亞胺等。
此等聚合物之製造,係藉由將加成聚合性單體及因應所需所添加之鏈轉移劑(相對於單體之質量為10%以下)溶解在有機溶劑中後,添加聚合起始劑進行聚合反應,之後添加聚合停止劑所製造。作為聚合起始劑之添加量,相對於單體之質量為1~10%,作為聚合停止劑之添加量為0.01~0.2質量%。作為所使用之有機溶劑,可舉例:丙二醇單甲基醚、丙二醇單丙基醚、乳酸乙酯、環己酮、甲基乙基酮、及二甲基甲醯胺等;作為鏈轉移劑為十二烷硫醇及十二烷基硫醇等;作為聚合起始劑為偶氮雙異丁腈及偶氮雙環己烷碳化腈等;又,作為聚合停止劑為4-甲氧基苯酚等。可自反應溫度為30~100℃、反應時間為1~48小時適宜選擇。
作為本發明之光阻下層膜形成組成物可含有交聯劑成分。作為該交聯劑,可舉例:三聚氰胺系、取代脲系、或此等之聚合物系等。較佳為具有至少2個的交聯形成取代基之交聯劑,例如:甲氧基甲基化甘脲、丁氧基甲基化甘脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯胍胺、丁氧基甲基化苯胍胺、甲氧
基甲基化脲、丁氧基甲基化脲、甲氧基甲基化硫脲、或甲氧基甲基化硫脲等的化合物。又,可使用此等之化合物的縮合體。
又,作為上述交聯劑可使用耐熱性高的交聯劑。作為耐熱性較高的交聯劑,較佳為可使用分子內含有具有芳香族環(例如苯環、萘環)之交聯形成取代基之化合物。
該化合物可舉例具有下述式(2)之部分構造之化合物、或具有下述式(3)之重覆單位之聚合物或寡聚物。
式(2)中,R10及R11分別為氫原子、碳數1~10之烷基,或碳數6~20之芳基,n10為1~4之整數,n11為1~(5-n10)之整數,(n10+n11)為2~5之整數。
式(3)中,R12為氫原子或碳數1~10之烷基,R13為碳數1~10之烷基,n12為1~4之整數,n13為0~(4-n12),(n12+n13)為1~4之整數。寡聚物及聚合物係可使用重覆單位構造之數為2~100、或2~50之範圍內。
此等之烷基及芳基可以上述烷基及芳基為例示。
式(2)、式(3)之化合物、聚合物、寡聚物可以例示如以下。
上述化合物可自旭有機材工業(股)、本州化學工業(股)之製品取得。例如在上述交聯劑之式(2-21)之化合物可自旭有機材工業(股)商品名TM-BIP-A取得,又,式(2-22)之化合物,可自本州化學工業(股)商品名TMOM-BP取得。
交聯劑之添加量係依據所使用之塗佈溶劑、所使用之底層基板、所要求之溶液黏度、所要求之膜形狀等而變動,但相對於全固體成份可使用為0.001~80質量%,較佳為0.01~50質量%,更佳為0.05~40質量%。此
等交聯劑雖有因為自縮合而產生交聯反應之情形,但若在本發明之上述之聚合物中存在交聯性取代基時,可與此等之交聯性取代基產生交聯反應。
本發明中,作為為了促進上述交聯反應之觸媒,可調配例如:p-甲苯磺酸、三氟甲烷磺酸、吡啶鎓p-甲苯磺酸、水楊酸、磺基水楊酸、檸檬酸、安息香酸、羥基安息香酸、萘羧酸等的酸性化合物或/及2,4,4,6-四溴環己二烯酮、安息香甲苯磺酸酯、2-硝基苄基甲苯磺酸酯、其他有機磺酸烷基酯等的熱酸產生劑。調配量相對於全固體成份為0.0001~20質量%,較佳為0.0005~10質量%,更佳為0.01~3質量%。
本發明之微影用塗佈型下層膜形成組成物,為微影步驟中使與被覆於上層之光阻之酸性度一致,可添加光酸產生劑。作為較佳的光酸產生劑,可舉例例如:雙(4-t-丁基苯基)碘鎓三氟甲烷磺酸鹽、三苯基鋶鎓三氟甲烷磺酸鹽等的鎓鹽系光酸產生劑類、苯基-雙(三氯甲基)-s-三嗪等的鹵素含有化合物系光酸產生劑類、安息香甲苯磺酸酯、N-羥基琥珀醯亞胺三氟甲烷磺酸鹽等的磺酸系光酸產生劑類等。上述光酸產生劑相對於全固體成份為0.2~10質量%,較佳為0.4~5質量%。
本發明之微影用光阻下層膜材料中,除了上述以外,因應所需可另外添加吸光劑、液流調整劑、接著補助劑、界面活性劑等。
作為另外的吸光劑,可舉例例如:「工業用
色素之技術與市場」(CMC出版)或「染料便覧」(有機合成化學協會編)所記載之市售之吸光劑,可適合使用例如C.I.Disperse Yellow 1,3,4,5,7,8,13,23,31,49,50,51,54,60,64,66,68,79,82,88,90,93,102,114及124;C.I.D isperse Orange1,5,13,25,29,30,31,44,57,72及73;C.I.Disperse Red 1,5,7,13,17,19,43,50,54,58,65,72,73,88,117,137,143,199及210;C.I.Disperse Violet 43;C.I.Disperse Blue 96;C.I.Fluorescent Brightening Agent 112,135及163;C.I.Solvent Orange2及45;C.I.Solvent Red 1,3,8,23,24,25,27及49;C.I.Pigment Green 10;C.I.Pigment Brown 2等。上述吸光劑,一般可以相對於微影用光阻下層膜材料之全固體成份為10質量%以下,較佳為5質量%以下之比例來調配。
液流調整劑主要添加目的為使光阻下層膜形成組成物之流動性提昇,特別是在焙燒步驟中,提高光阻下層膜之膜厚均勻性的提升,或提高對孔洞內部之光阻下層膜形成組成物之充填性。作為具體例,可舉例:鄰苯二甲酸二甲酯、鄰苯二甲酸二乙酯、鄰苯二甲酸二異丁酯、鄰苯二甲酸二己酯、鄰苯二甲酸丁基異癸基酯等的鄰苯二甲酸衍生物、己二酸二正丁酯、己二酸二異丁酯、己二酸二異辛酯、己二酸辛基癸基酯等的己二酸衍生物、馬來酸二正丁酯、馬來酸二乙酯、馬來酸二壬酯等的馬來酸衍生物、油酸甲酯、油酸丁酯、油酸四氫糠酯等的油酸衍生
物、或硬脂酸正丁酯、硬脂酸甘油酯等的硬脂酸衍生物。此等之液流調整劑相對於微影用光阻下層膜材料之全固體成份,一般以未滿30質量%之比例調配。
接著補助劑之添加目的主要為將基板或光阻與光阻下層膜形成組成物之密著性提昇,特別是顯影步驟中光阻不剝離。作為具體例,可舉例:三甲基氯矽烷、二甲基乙烯基氯矽烷、甲基二苯基氯矽烷、氯甲基二甲基氯矽烷等的氯矽烷類、三甲基甲氧基矽烷、二甲基二乙氧基矽烷、甲基二甲氧基矽烷、二甲基乙烯基乙氧基矽烷、二苯基二甲氧基矽烷、苯基三乙氧基矽烷等的烷氧基矽烷類、六甲基二矽氮烷、N,N’-雙(三甲基矽烷基)脲、二甲基三甲基矽烷胺、三甲基矽烷基咪唑等的矽氮烷類、乙烯基三氯矽烷、γ-氯丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷等的矽烷類、苯并***、苯并咪唑、吲唑、咪唑、2-巰基苯并咪唑、2-巰基苯并噻唑、2-巰基苯并噁唑、脲唑、硫脲嘧啶、巰基咪唑、巰基嘧啶等的雜環式化合物、或1,1-二甲基脲、1,3-二甲基脲等的脲、或硫脲化合物。此等之接著補助劑相對於微影用光阻下層膜材料之全固體成份,一般以未滿5質量%,較佳為未滿2質量%之比例來調配。
本發明之微影用光阻下層膜材料中,為了不產生針孔或條紋等,並進而提升對表面不均之塗佈性,可調配界面活性劑。作為界面活性劑,可舉例例如:聚氧乙烯月桂基醚、聚氧乙烯硬脂醯醚、聚氧乙烯十六烷醚、聚
氧乙烯油基醚等的聚氧乙烯烷基醚類、聚氧乙烯辛基苯酚醚、聚氧乙烯壬基苯酚醚等的聚氧乙烯烷基烯丙基醚類、聚氧乙烯.聚氧丙烯嵌段共聚合物類、去水山梨醇單月桂酸酯、去水山梨醇單棕櫚酸酯、去水山梨醇單硬脂酸酯、去水山梨醇單油酸酯、去水山梨醇三油酸酯、去水山梨醇三硬脂酸酯等的去水山梨醇脂肪酸酯類、聚氧乙烯去水山梨醇單月桂酸酯、聚氧乙烯去水山梨醇單棕櫚酸酯、聚氧乙烯去水山梨醇單硬脂酸酯、聚氧乙烯去水山梨醇三油酸酯、聚氧乙烯去水山梨醇三硬脂酸酯等的聚氧乙烯去水山梨醇脂肪酸酯類等的非離子系界面活性劑、EF-Top EF301、EF303、EF352((股)Tohkem Products製、商品名)、Megafac F171、F173、R-30(大日本油墨(股)製、商品名)、Fluorad FC430、FC431(住友3M(股)製、商品名)、AashiGuard AG710、Surflon S-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(股)製、商品名)等的氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業(股)製)等。此等之界面活性劑之調配量相對於本發明之微影用光阻下層膜材料之全固體成份一般為2.0質量%以下,較佳為1.0質量%以下。此等之界面活性劑可單獨添加、或組合2種以上來添加。
本發明中,作為將上述之聚合物及交聯劑成分、交聯觸媒等溶解之溶劑,可使用如:乙二醇單甲基醚、乙二醇單乙基醚、乙酸甲賽璐蘇、乙酸乙賽路蘇、二乙二醇單甲基醚、二乙二醇單乙基醚、丙二醇、丙二醇單
甲基醚、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚、丙二醇單乙基醚乙酸酯、丙二醇丙基醚乙酸酯、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-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、丙酮酸甲酯、丙酮酸乙酯、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯等。此等之有機溶劑可單獨或組合2種以上來使用。
進而可混合丙二醇單丁基醚、丙二醇單丁基醚乙酸酯等的高沸點溶劑使用。在此等之溶劑中,以丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、乳酸乙酯、乳酸丁酯、及環己酮等,對於平坦性之提昇為較佳。
本發明所使用之光阻係指光阻或電子線光阻。作為於本發明之微影用光阻下層膜之上方所塗佈之光阻,可使用負型、正型任一種,可舉例:由酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所成之正型光阻、具有藉由酸而分解並使鹼溶解速度提昇之基之黏合劑與光酸產生劑所成之化學增幅型光阻、鹼可溶性黏合劑與藉由酸而分解並使光阻之鹼溶解速度提昇之低分子化合物與光酸產生劑所成之化學增幅型光阻、具有藉由酸而分解將鹼溶解速度提昇之基之黏合劑,與藉由酸而分解並使光阻之鹼溶解速度提昇之低分子化合物與光酸產生劑所成之化學增幅型光阻、骨架具有Si原子之光阻等,可舉例例如Rohm and Haas
公司製、商品名APEX-E。
又,作為於本發明之微影用光阻下層膜之上方所塗佈之電子線光阻,可舉例例如:包含在主鏈含有Si-Si鍵結,且末端含有芳香族環之樹脂與藉由電子線之照射產生酸之酸產生劑所成之組成物;或,羥基為經包含N-羧基胺之有機基所取代之聚(p-羥基苯乙烯)與藉由電子線之照射產生酸之酸產生劑所成之組成物等。後者之電子線光阻組成物中,藉由電子線照射由酸產生劑所產生之酸,與聚合物側鏈之N-羧基胺氧基反應,聚合物側鏈分解成羥基而顯示鹼可溶性,並溶解在鹼顯影液中形成光阻圖型。藉由此電子線之照射產生酸之酸產生劑,可舉例:1,1-雙[p-氯苯基]-2,2,2-三氯乙烷、1,1-雙[p-甲氧基苯基]-2,2,2-三氯乙烷、1,1-雙[p-氯苯基]-2,2-二氯乙烷、2-氯-6-(三氯甲基)吡啶等的鹵素化有機化合物、三苯基硫鎓鹽、二苯基碘鎓鹽等的鎓鹽、硝基苄基甲苯磺酸酯、二硝基苄基甲苯磺酸酯等的磺酸酯。
作為具有使用本發明之微影用光阻下層膜材料所形成之光阻下層膜之光阻之顯影液,可使用:氫氧化鈉、氫氧化鉀、碳酸鈉、矽酸鈉、偏矽酸鈉、氨水等的無機鹼類、乙基胺、n-丙基胺等的第一胺類、二乙基胺、二-N-丁基胺等的第二胺類、三乙基胺、甲基二乙基胺等的第三胺類、二甲基乙醇胺、三乙醇胺等的醇胺類、四甲基銨羥化物、四乙基銨羥化物、膽鹼等的第4級銨鹽、吡咯、哌啶等的環狀胺類、等的鹼類之水溶液。再者,亦可
在上述鹼類之水溶液中,適當量添加異丙基醇等的醇類、非離子系等的界面活性劑使用。此等之中較佳的顯影液為第四級銨鹽,更佳為四甲基銨羥化物及膽鹼。
又,作為顯影液可使用有機溶劑。可列舉例如: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、二乙二醇單乙基醚乙酸酯、二乙二醇單丙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二乙二醇單苯基醚乙酸酯、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、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-甲氧基丙酸酯等為例。再者,亦可在此等之顯影液中加入界面活性劑等。作為顯影之條件可自溫度5~50℃、時間10~600秒適宜選擇。
接著,對於本發明之光阻圖型形成法進行說明,藉由旋轉器、塗佈機等的適當的塗佈方法,於精密積體電路元件之製造所使用之基板(例如矽/二酸化矽被覆、玻璃基板、ITO基板等的透明基板)上塗佈光阻下層膜形成組成物後,烘烤後使其硬化製作塗佈型下層膜。在此,作為光阻下層膜之膜厚較佳為0.01~3.0μm。又,作為塗佈後焙燒之條件為80~350℃下0.5~120分鐘。之後,在光阻下層膜上,直接、或因應所需將1層至數層之塗膜材料成膜至光阻下層膜上後,塗佈光阻並通過特定的遮罩進行光或電子線之照射,藉由顯影、潤濕、乾燥可得到良好的光阻圖型。因應所需,亦可進行光或電子線之照射後加熱(PEB:Post Exposure Bake)。又,藉由前述步驟來顯影除去了光阻之部分的光阻下層膜藉由乾蝕刻來除去,而於基板上形成所期望之圖型。
在上述光阻之曝光之光為近紫外線、遠紫外線、或極端紫外線(例如EUV、波長13.5nm)等的化學線,可使用例如248nm(KrF雷射光)、193nm(ArF雷射光)、157nm(F2雷射光)等的波長之光。光照射只要是自光酸產生劑來產生酸之方法即可,無特別限制可為使用,曝光量為1~2000mJ/cm2、10~1500mJ/cm2、或50~1000mJ/cm2。
又,電子線光阻之電子線照射,可使用例如電子線照射裝置來照射。
本發明中,可經由以下步驟來製造半導體裝置:藉由光阻下層膜形成組成物,在半導體基板上形成該光阻下層膜之步驟、於其上方形成光阻膜之步驟、藉由光或電子線照射與顯影形成光阻圖型之步驟、藉由光阻圖型蝕刻該光阻下層膜之步驟、及經由已圖型化之光阻下層膜來加工半導體基板之步驟。
今後,光阻圖型朝微細化進行時,由於會產生所謂解析度之問題或光阻圖型在顯像後崩塌之問題,故期望光阻之薄膜化。因而,於基板加工時難以獲得充分之光阻圖型膜厚,不僅光阻圖型,在光阻與經加工半導體基板之間所形成之光阻下層膜亦變得必須具有作為基板加工時之遮罩之功能之製程。與作為如此般製程使用之光阻下層膜之以往之高蝕刻速率性光阻下層膜不同,要求具有與光阻接近之乾蝕刻速度之選擇比之微影用光阻下層膜、具有較光阻小之乾蝕刻速度之選擇比之微影用光阻下層膜、或具有較半導體基板小之乾蝕刻速度之選擇比之微影用光阻下層膜。又,對如此般的光阻下層膜亦可賦予防反射能力,且可兼具以往的防反射膜之機能。
另一方面,為了得到微細的光阻圖型開始使用以下製程:在光阻下層膜乾蝕刻時,使光阻圖型與光阻下層膜較光阻顯影時之圖型寬度更為細。作為如此般的製程用之光阻下層膜,與以往之高蝕刻速率性防反射膜不
同,要求具有與光阻接近之乾蝕刻速度之選擇比之光阻下層膜。又,對如此般的光阻下層膜亦可賦予防反射能力,且可兼具以往的防反射膜之機能。
本發明中,可於基板上將本發明之光阻下層膜成膜後,在光阻下層膜上直接、或因應所需將1層至數層之塗膜材料成膜於光阻下層膜上後,塗佈光阻。由此,即使在光阻之圖型寬度變窄,為了防止圖型崩塌而包覆較薄的光阻之情形時,可藉由選擇適當的蝕刻氣體來進行基板的加工。
即,可藉由以下步驟來製造半導體裝置:藉由光阻下層膜形成組成物在半導體基板上形成該光阻下層膜之步驟、於其上方藉由含有矽成份等之塗膜材料形成硬遮罩或藉由蒸鍍形成硬遮罩(例如氮化氧化矽)之步驟、進而於其上方形成光阻膜之步驟、藉由光或電子線之照射與顯影形成光阻圖型之步驟、藉由光阻圖型用鹵素系氣體蝕刻硬遮罩之步驟、經由已圖型化之硬遮罩用氧系氣體或氫系氣體蝕刻該光阻下層膜之步驟、及經由已圖型化之光阻下層膜用鹵素系氣體來加工半導體基板之步驟。
本發明之微影用光阻下層膜形成組成物,當考慮作為防反射膜之效果時,由於光吸收部位被包裹在骨架中,所以加熱乾燥時不存在對光阻之擴散物,又,由於光吸收部位具有充份較大的吸光性能,故防止反射光效果高。
本發明之微影用光阻下層膜形成組成物,熱
穩定性高,可以防止燒成時之分解物對上層膜之污染,又,可使燒成步驟之溫度範圍更為充裕。再者,本發明之微影用光阻下層膜材料,依製程條件可作為具有防止光反射之機能、與進而防止基板與光阻之相互作用或防止對於在光阻所使用之材料或對光阻之曝光時所生成物質之基板之不良作用之機能的膜來使用。
又,本發明係包含上述之式(5)之單位構造之聚合物。式(5)中記載之有機基係可舉例上述之式(1)之例示。
在100ml茄型燒瓶中,放入吡咯(東京化成工業(股)製)6.0g、1-萘醛(東京化成工業(股)製)14.1g、p-甲苯磺酸一水合物(東京化成工業(股)製)1.8g、甲苯(關東化學(股)製)32.8g。之後,將燒瓶內以氮取代後,在室溫下攪拌約2小時。反應結束後,以四氫呋喃(關東化學(股)製)15g稀釋。稀釋液滴入於甲醇(關東化學(股)製)1300g中,使其再沉澱。抽吸過濾所得到的沉澱物,以甲醇洗淨過濾物後,在85℃下進行一晚減壓乾燥,可得到酚醛清漆樹脂16.4g。所得到的聚合物相當於式(1-1)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為7,500。
在200ml茄型燒瓶中,放入吡咯(東京化成工業(股)製)6.0g、9-蒽羧基醛(東京化成工業(股)製)18.6g、p-甲苯磺酸一水合物(東京化成工業(股)製)1.8g、甲苯(關東化學(股)製)61.6g。之後,將燒瓶內以氮取代後,在室溫下攪拌同時滴入吡咯(東京化成工業(股)製)6.0g。滴下結束後,在室溫下攪拌約12小時。反應結束後,將反應溶液滴入己烷(關東化學(股)製)1200g中,使其再沉澱。抽吸過濾所得到的沉澱物,以己烷洗淨過濾物後,在85℃下進行一晚減壓乾燥,可得到酚醛清漆樹脂20.3g。所得到的聚合物相當於式(1-2)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為2,000。
在100ml茄型燒瓶中,放入吡咯(東京化成工業(股)製)2.0g、9-芘羧基醛(東京化成工業(股)製)7.0g、p-甲苯磺酸一水合物(東京化成工業(股)製)0.6g、甲苯(關東化學(股)製)28.6g。之後,將燒瓶內以氮取代後,在室溫下攪拌同時滴入吡咯(東京化成工業(股)製)2.0g。滴下結束後,在室溫下攪拌約1小時,再加熱後回流攪拌約22小時。反應結束後,加入四氫呋喃(關東化學(股)製)15g將析出之固體予以溶解。將溶液滴入己烷(關東化學(股)製)1200g中,使其再沉澱。抽吸過濾所得到的沉澱物,以己烷洗淨過濾物後,在85℃下進行一晚減壓乾燥,可得
到酚醛清漆樹脂6.9g。所得到的聚合物相當於式(1-3)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為900。
在100ml茄型燒瓶中,放入吡咯(東京化成工業(股)製)6.0g、4-羥基苯甲醛(東京化成工業(股)製)10.9g、甲烷磺酸(東京化成工業(股)製)0.17g、丙二醇單甲基醚51.3g。之後,將燒瓶內以氮取代後,在室溫下攪拌同時滴入吡咯(東京化成工業(股)製)6.0g。滴下結束後,加熱並回流攪拌約15小時。反應結束後,使與離子交換樹脂接觸後除去甲烷磺酸,可得到固形分17.6%的酚醛清漆樹脂溶液66.7g。所得到的聚合物相當於式(1-4)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為660。
在200ml茄型燒瓶中,放入吡咯(東京化成工業(股)製)7.0g、1-萘醛(東京化成工業(股)製)13.4g、6-羥基-2-萘醛(東京化成工業(股)製)3.7g、甲烷磺酸(東京化成工業(股)製)0.41g、丙二醇單甲基醚57.3g。之後,將燒瓶內以氮取代後,在室溫下攪拌同時滴入吡咯(東京化成工業(股)製)7.0g。滴下結束後,在室溫下攪拌約14小時。反應結束後,將反應溶液滴入甲醇(關東化學(股)製)1600g中,使其再沉澱。抽吸過濾所得到的沉澱物,以甲醇洗淨過濾
物後,在85℃下進行一晚減壓乾燥,可得到酚醛清漆樹脂11.9g。所得到的聚合物相當於式(1-5)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為2,300。
在100ml茄型燒瓶中,放入1-甲基吡咯(東京化成工業(股)製)6.0g、1-萘醛(東京化成工業(股)製)11.6g、甲烷磺酸(東京化成工業(股)製)0.07g、丙二醇單甲基醚乙酸酯52.9g。之後,將燒瓶內以氮取代後,在室溫下攪拌同時滴入1-甲基吡咯(東京化成工業(股)製)6.0g。滴下結束後,在室溫下攪拌四日。反應結束後,將反應溶液滴入甲醇(關東化學(股)製)1500g中,使其再沉澱。抽吸過濾所得到的沉澱物,以甲醇洗淨過濾物後,在85℃下進行一晚減壓乾燥,可得到酚醛清漆樹脂12.1g。所得到的聚合物相當於式(1-6)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為2,200。
在100ml茄型燒瓶中,放入1-苯基吡咯(東京化成工業(股)製)6.0g、1-萘醛(東京化成工業(股)製)6.5g、丙二醇單甲基醚乙酸酯37.7g。之後,將燒瓶內以氮取代後,在室溫下攪拌同時滴入甲烷磺酸(東京化成工業(股)製)0.04g。滴下結束後,加熱至110℃並攪拌約17小時。反應結束後,將反應溶液滴入甲醇(關東化學(股)製)1000g
中,使其再沉澱。抽吸過濾所得到的沉澱物,以甲醇洗淨過濾物後,在85℃下進行一晚減壓乾燥,可得到酚醛清漆樹脂9.5g。所得到的聚合物相當於式(1-7)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為2,500。
在100ml茄型燒瓶中,放入1-苯基吡咯(東京化成工業(股)製)7.0g、4-羥基苯甲醛(東京化成工業(股)製)6.0g、丙二醇單甲基醚乙酸酯30.4g。之後,將燒瓶內以氮取代後,在室溫下攪拌同時滴入甲烷磺酸(東京化成工業(股)製)0.05g。滴下結束後,加熱至110℃並攪拌約17小時。反應結束後,使用離子交換樹脂接觸後除去甲烷磺酸,可得到固形分24.5%的酚醛清漆樹脂溶液42.4g。所得到的聚合物相當於式(1-8)。藉由GPC以聚苯乙烯換算所測定之重量平均分子量Mw為2,300。
氮氣下,在100ml四口燒瓶中,加入咔唑(10g、0.060mol、東京化成工業(股)製)、苯甲醛(6.41g、0.060mol、純正化學(股)製)、p-甲苯磺酸一水合物(1.19g、0.060mol、關東化學(股)製),再加入1,4-二噁烷(15g、關東化學(股)製)並攪拌,昇溫至100℃使其溶解而開始進行聚合。2小時後,放冷至60℃後,加入三氯甲烷(50g、關東化學(股)製)稀釋,使其對甲醇(250g、關東化學(股)製)再
沉澱。過濾所得到的沉澱物,於減壓乾燥機中以60℃、10小時,再以120℃、24小時進行乾燥,可得到作為目的之高分子化合物8.64g。此者為包含下述式(4-1)之單位構造之聚合物。藉由高分子化合物(式(4-1))之GPC之聚苯乙烯換算所測定之重量平均分子量Mw為4000,多分散度Mw/Mn為1.69。
在合成例1所得之0.8g的聚合物中,加入丙二醇單甲基醚乙酸酯1.0g、丙二醇單甲基醚2.5g、環己酮6.4g、作為交聯劑之TMOM-BP(上述式(2-22)、本州化學工業(股)製)0.16g、TAG2689 0.016g後使其溶解,調製使用於利用多層膜進行微影製程之光阻下層膜形成組成物之溶液。
在合成例2所得之2.0g的聚合物中,加入丙二醇單甲基醚乙酸酯9.7g、丙二醇單甲基醚6.5g、環己酮16.2
g、四甲氧基甲基甘脲0.4g、吡啶鎓對甲苯磺酸酯0.04g後使其溶解,調製使用於利用多層膜進行微影製程之光阻下層膜形成組成物之溶液。
在合成例3所得之0.8g的聚合物中,加入丙二醇單甲基醚乙酸酯1.0g、丙二醇單甲基醚2.5g、環己酮6.4g、作為交聯劑之TMOM-BP(上述式(2-22)、本州化學工業(股)製)0.16g、TAG2689 0.016g後使其溶解,調製使用於利用多層膜進行微影製程之光阻下層膜形成組成物之溶液。
在合成例4所得之12.0g的聚合物溶液中,加入丙二醇單甲基醚乙酸酯4.6g、丙二醇單甲基醚6.3g、環己酮2.3g、作為交聯劑之TMOM-BP(上述式(2-22)、本州化學工業(股)製)0.4g、吡啶鎓對甲苯磺酸酯0.03g後使其溶解,調製使用於利用多層膜進行微影製程之光阻下層膜形成組成物之溶液。
在合成例5所得之2.0g的聚合物中,加入丙二醇單甲基醚乙酸酯11.0g、丙二醇單甲基醚6.6g、環己酮4.4g、作為交聯劑之TMOM-BP(上述式(2-22)、本州化學
工業(股)製)0.4g、吡啶鎓對甲苯磺酸酯0.03g後使其溶解,調製使用於利用多層膜之微影製程之光阻下層膜形成組成物之溶液。
在合成例6所得之1.5g的聚合物中,加入丙二醇單甲基醚乙酸酯11.5g、丙二醇單甲基醚3.3g、環己酮1.6g、作為交聯劑之TMOM-BP(上述式(2-22)、本州化學工業(股)製)0.3g、吡啶鎓對甲苯磺酸酯0.02g後使其溶解,調製使用於利用多層膜之微影製程之光阻下層膜形成組成物之溶液。
在合成例7所得之1.5g的聚合物中,加入丙二醇單甲基醚乙酸酯11.5g、丙二醇單甲基醚3.3g、環己酮1.6g、作為交聯劑之TMOM-BP(上述式(2-22)、本州化學工業(股)製)0.3g、吡啶鎓對甲苯磺酸酯0.02g後使其溶解,調製使用於利用多層膜之微影製程之光阻下層膜形成組成物之溶液。
在合成例8所得之12.0g的聚合物溶液中,加入丙二醇單甲基醚乙酸酯6.4g、丙二醇單甲基醚13.5g、環己酮3.2g、作為交聯劑之TMOM-BP(上述式(2-22)、本州化學
工業(股)製)0.6g、吡啶鎓對甲苯磺酸酯0.04g後使其溶解,調製使用於利用多層膜之微影製程之光阻下層膜形成組成物之溶液。
在合成例4所得之12.0g的聚合物溶液中,加入丙二醇單甲基醚乙酸酯4.6g、丙二醇單甲基醚6.3g、環己酮2.3g、四甲氧基甲基甘脲0.4g、吡啶鎓對甲苯磺酸酯0.03g後使其溶解,調製使用於利用多層膜之微影製程之光阻下層膜形成組成物之溶液。
在上述比較合成例1所得之高分子化合物(式(4-1))的1.0g中,混合四甲氧基甲基甘脲0.2g、吡啶鎓對甲苯磺酸酯0.02g、Megafac R-30(大日本油墨化學(股)製、商品名)0.003g、丙二醇單甲基醚2.3g、丙二醇單甲基醚乙酸酯4.6g、環己酮16.3g來作為溶液。之後,使用孔徑0.10μm的聚乙烯製微濾器來過濾,使用孔徑0.05μm的聚乙烯製微濾器再過濾,調製使用於利用多層膜之微影製程之光阻下層膜形成組成物之溶液。
使用旋轉塗佈機,將實施例1~9、及比較例1所調製之各光阻下層膜形成組成物溶液分別塗佈在矽晶圓上。
在加熱板上以250℃燒成1分鐘,形成光阻下層膜(膜厚0.05μm)。又,使用光橢圓計以分光偏振波長193nm下,測定此等之光阻下層膜之屈折率(n值)及光學吸光係數(k值,亦稱為衰減係數)。將結果表示於表1。
使用旋轉器,將實施例1~9、及比較例1所調製之各光阻下層膜形成組成物溶液塗佈在矽晶圓上,在加熱板上以250℃的溫度下加熱1分鐘,形成光阻下層膜(膜厚0.2μm)。又,將此等之光阻下層膜浸漬於使用於光阻之溶劑之乳酸乙酯、丙二醇單甲基醚及丙二醇單甲基醚乙酸酯中,並確認不溶於該溶劑中。
藉由旋轉塗佈機,將實施例1~9、及比較例1所得之本發明之微影用下層膜形成組成物溶液,塗佈在具有孔洞(直徑0.13μm、深度0.7μm)之附SiO2晶圓基板上。圖型係從孔洞中心至鄰近的孔洞中心之間隔為該孔洞的直徑之1倍之圖型。
旋轉塗佈機塗佈後,在加熱板上以240℃燒成1分鐘,形成下層膜。使用掃描式電子顯微鏡(SEM),觀察具有塗佈有實施例1所得之本發明之微影用下層膜形成組成物之孔洞之附SiO2晶圓基板之斷面形狀,將利用下層膜之埋覆性依以下之基準進行評估。若下層膜可無空孔埋覆孔洞內之情形時為良好(表2中標記為「○」),若下層膜在孔洞內產生空孔之情形時為不良(表2中標記「×」)。
對於乾蝕刻速度之測定係使用下述之蝕刻裝置及蝕刻氣體。
蝕刻裝置:RIE-10NR(Samco(股)製)
蝕刻氣體:CF4
藉由旋轉器,將實施例1~9、及比較例1所調製之各光阻下層膜形成組成物溶液塗佈在矽晶圓上。在加熱板上以240℃的溫度加熱1分鐘,形成光阻下層膜(膜厚0.2μm)。對於該光阻下層膜,使用作為蝕刻氣體之CF4氣體來測定乾蝕刻速度。再者,藉由旋轉器,使苯酚酚醛清漆樹脂0.7g溶解於丙二醇單甲基醚10g中之溶液塗佈在矽晶圓上,以240℃的溫度加熱1分鐘後,形成苯酚酚醛清漆樹脂膜。對於該樹脂膜,使用作為蝕刻氣體之CF4氣體來測定乾蝕刻速度,並進行與由實施例1~9、及比較例1之光阻下層膜形成組成物所形成之各光阻下層膜之乾蝕刻速度之比較。將該結果表示於下述表3。表3之乾蝕刻速度比係相對於上述苯酚酚醛清漆樹脂膜之乾蝕刻速度,各光阻下層膜之乾蝕刻速度(上述各光阻下層膜)/(苯酚酚醛清漆樹脂膜)。
[表3]
由此,可得知藉由本發明相關之光阻下層膜形成組成物所得到的光阻下層膜,可提供與以往的高蝕刻速率性防反射膜有所不同,且具有接近光阻或較光阻小之乾蝕刻速度之選擇比、較半導體基板小之乾蝕刻速度之選擇比,再者亦能兼具作為防反射膜之效果之優越的塗佈型光阻下層膜。
可提供一優異的光阻下層膜,其具有:接近光阻之乾蝕刻速度之選擇比、較光阻小之乾蝕刻速度之選擇比或較半導體基板小之乾蝕刻速度之選擇比。
Claims (10)
- 一種光阻下層膜形成組成物,其包含含有下述式(1)之單位構造之聚合物:
- 如請求項1之光阻下層膜形成組成物,其中,式(1)的R3為苯環、萘環、蒽環或芘環,R4為氫原子,n為0。
- 如請求項1或請求項2之光阻下層膜形成組成物,其中,進而包含交聯劑。
- 如請求項1至請求項3中任一項之光阻下層膜形成組成物,其中,進而包含酸及/或酸產生劑。
- 一種光阻下層膜,其係藉由將請求項1至請求項4中任一項之光阻下層膜形成組成物塗佈於半導體基板上並經燒成而得。
- 一種使用於半導體之製造之光阻圖型之形成方法,其係包含將請求項1至請求項4中任一項之光阻下層膜形成組成物塗佈於半導體基板上並經燒成而形成下層膜之步驟。
- 一種半導體裝置之製造方法,其係包含於半導體基板上,藉由請求項1至請求項4中任一項之光阻下層膜形成組成物形成下層膜之步驟、於其上方形成光阻膜之步驟、藉由光或電子線之照射與顯影形成光阻圖型之步驟、藉由光阻圖型蝕刻該下層膜之步驟、及利用已圖型化之下層膜來加工半導體基板之步驟。
- 一種半導體裝置之製造方法,其係包含於半導體基板上,藉由請求項1至請求項4中任一項之光阻下層膜形成組成物形成下層膜之步驟、於其上方形成硬遮罩之步驟、於其上方進而形成光阻膜之步驟、藉由光或電子線之 照射與顯影形成光阻圖型之步驟、藉由光阻圖型蝕刻硬遮罩之步驟、利用已圖型化之硬遮罩來蝕刻該下層膜之步驟、及利用已圖型化之下層膜加工半導體基板之步驟。
- 如請求項8之製造方法,其中,硬遮罩係藉由無機物的蒸鍍而得到者。
- 一種聚合物,其係含有下述式(5)之單位構造:
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CN202159215U (zh) * | 2011-08-01 | 2012-03-07 | 京东方科技集团股份有限公司 | 阵列基板和液晶显示面板 |
JP5643167B2 (ja) * | 2011-09-02 | 2014-12-17 | 株式会社ダイセル | 架橋性組成物 |
WO2013047516A1 (ja) * | 2011-09-29 | 2013-04-04 | 日産化学工業株式会社 | ジアリールアミンノボラック樹脂 |
US20160147151A1 (en) * | 2013-06-25 | 2016-05-26 | Nissan Chemical Industries, Ltd. | Resist underlayer film-forming composition contaning pyrrole novolac resin |
-
2014
- 2014-06-23 US US14/900,406 patent/US20160147151A1/en not_active Abandoned
- 2014-06-23 CN CN201480035408.0A patent/CN105324719A/zh active Pending
- 2014-06-23 KR KR1020157034503A patent/KR20160023671A/ko not_active Application Discontinuation
- 2014-06-23 JP JP2015524037A patent/JP6436313B2/ja active Active
- 2014-06-23 WO PCT/JP2014/066560 patent/WO2014208499A1/ja active Application Filing
- 2014-06-25 TW TW103121880A patent/TW201512304A/zh unknown
-
2018
- 2018-05-22 JP JP2018098010A patent/JP6734569B2/ja active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI691795B (zh) * | 2016-04-29 | 2020-04-21 | 南韓商東友精細化工有限公司 | 硬遮罩之組合物 |
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JP6734569B2 (ja) | 2020-08-05 |
JP6436313B2 (ja) | 2018-12-12 |
US20160147151A1 (en) | 2016-05-26 |
CN105324719A (zh) | 2016-02-10 |
JPWO2014208499A1 (ja) | 2017-02-23 |
KR20160023671A (ko) | 2016-03-03 |
JP2018168375A (ja) | 2018-11-01 |
WO2014208499A1 (ja) | 2014-12-31 |
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