TWI727044B - 光阻下層膜形成組成物 - Google Patents
光阻下層膜形成組成物 Download PDFInfo
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- TWI727044B TWI727044B TW106116130A TW106116130A TWI727044B TW I727044 B TWI727044 B TW I727044B TW 106116130 A TW106116130 A TW 106116130A TW 106116130 A TW106116130 A TW 106116130A TW I727044 B TWI727044 B TW I727044B
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
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Abstract
Description
本發明係有關微影步驟用光阻下層膜形成組成物。特別是有關形成作為遮罩材用時具有耐蝕性,且相對於具有段差、凹部及/或凸部之表面具有填埋性的光阻下層膜用之組成物。
製造半導體裝置時係以微影步驟進行微細加工。已知該微影步驟中以KrF準分子雷射、ArF準分子雷射等之紫外線雷射使基板上之光阻層曝光時會有,受起因於基板表面反射該紫外線雷射而發生之定在波影響,而無法形成具有所希望之形狀的光阻圖型之問題。為了解決該問題,係採用基板與光阻層之間設置光阻下層膜(防反射膜)。其次已知形成光阻下層膜用之組成物如,使用酚醛清漆樹脂(專利文獻1、專利文獻2、專利文獻3及專利文獻4)。
伴隨著光阻圖型的微細化而要求光阻層薄膜 化之情形下,已知有至少形成二層光阻下層膜,以該光阻下層膜作為遮罩材用之微影步驟。形成前述至少二層之材料如,有機樹脂(例如丙烯酸樹脂、酚醛清漆樹脂)、矽樹脂(例如有機聚矽氧烷)、無機矽化合物(例如SiON、SiO2)。以由上述有機樹脂所形成之圖型作為遮罩進行蝕刻時,該圖型需對蝕刻氣體(例如氟碳)具有耐蝕性。前述專利文獻1、專利文獻2及專利文獻3曾揭示可形成該類圖型,且具有填埋性之有機樹脂。
[專利文獻1]特開2014-24831號公報
[專利文獻2]國際公開第2014/024836號
[專利文獻3]國際公開第2013/146670號
[專利文獻4]國際公開第2010/147155號
製造半導體裝置時有關塗佈光阻下層膜形成組成物之過程中,預濕處理(使塗佈組成物之前的表面濕潤)、邊緣清洗(去除殘留於基板周邊部之組成物)、背面清洗(去除殘留於基板背面之組成物)等之步驟所使用的溶劑為2-羥基異丁酸甲酯。但光阻下層膜形成組成物相對於2-羥基異丁酸甲酯之溶解性較低時,持續將該光阻下層膜 形成組成物塗佈於基板時所使用之塗佈機,使用於塗佈2-羥基異丁酸甲酯時,恐使接連該塗佈機之排放配管阻塞,而有無法排出廢液之問題。該問題係起因於該配管內會附著光阻下層膜形成組成物混合2-羥基異丁酸甲酯後所生成之該光阻下層膜形成組成物之析出物。
本發明之目的為,提供溶解於2-羥基異丁酸甲酯之光阻下層膜形成組成物。本發明之另一目的為,提供形成相對於氟碳酸之蝕刻氣體具有比先前更優良之耐蝕性,且相對於具有段差、凹部及/或凸部之表面具有填埋性的光阻下層膜用之組成物。
[式(1a)及(1b)中,2個R1表示各自獨立之碳原子數1至10之烷基、碳原子數2至6之鏈烯基、芳香族烴基、鹵原子、硝基或胺基,2個R2表示各自獨立之氫原子、碳原子數1至10之烷基、碳原子數2至6之鏈烯基、縮醛、醯基或縮水甘油基,R3表示可具有取代基之芳香族烴基或雜環基,R4表示氫原子、苯基或萘基,同一碳原子所鍵結之R3與R4各自表示苯基時可相互鍵結形成芴環,2個k表示各自獨立之0或1,m表示3至500之整數,p表示3至500之整數,X表示苯環,該苯環所鍵結之2個-C(CH3)2-基為間位或對位之關係]
所表示之重覆結構單位的聚合物及溶劑之光阻下層膜形成組成物。
前述聚合物為必須具有前述式(1a)所表示之重覆結構單位,又可任意具有前述式(1b)所表示之重覆結構單位。
上述R1表示鹵原子時,該鹵原子如,氯原子、溴原子。上述芳香族烴基之芳香環可為單環、多環(包含雙環)、或雜環中任一種,例如苯基、聯苯基、萘基、蒽基、芘基、噻吩基、吡啶基。上述R3所表示之可具有取代基之芳香族烴基就耐蝕性及填埋性觀點,較佳為苯基、萘基、蒽基及芘基。又,芳香族烴基之取代基如,甲氧基、醛基。
本發明之光阻下層膜形成組成物可另含有交聯劑、酸性化合物、熱酸發生劑及表面活性劑中之至少一種作為任意成份。
本發明之第二態樣為包含藉由將本發明之光阻下層膜形成組成物塗佈於具有段差、凹部及/或凸部之基板表面再焙燒而形成第一層之光阻下層膜的步驟、於前述第一層之光阻下層膜上形成有機聚矽氧烷膜作為第二層之光阻下層膜的步驟、於前述第二層之光阻下層膜上形成光阻圖型之步驟、以前述光阻圖型作為遮罩蝕刻前述第二層之光阻下層膜的步驟、以蝕刻後之前述第二層之光阻下層膜的圖型作為遮罩蝕刻前述第一層之光阻下層膜的步驟,及以蝕刻後之前述第一層之光阻下層膜之圖型作為遮 罩蝕刻前述具有段差、凹部及/或凸部之表面的步驟之半導體裝置的製造方法。
前述形成第一層之光阻下層膜的步驟及/或前述形成第二層之光阻下層膜的步驟中,可另使用2-羥基異丁酸甲酯,相對於前述具有段差、凹部及/或凸部之基板進行預濕處理、邊緣清洗及背面清洗。
使用本發明之光阻下層膜形成組成物所形成之光阻下層膜為,相對於氟碳般之蝕刻氣體具有耐蝕性,且相對於具有凹部及/或凸部之表面具有優良填埋性。另外本發明之光阻下層膜形成組成物可溶解於2-羥基異丁酸甲酯,故可抑制接連於塗佈機之排放配管內附著析出物,而解決該配管阻塞之問題。
圖1為,表示進行使用實施例1調製之光阻下層膜形成組成物之填埋試驗的結果之剖面SEM照片。
圖2為,表示進行使用實施例2調製之光阻下層膜形成組成物之填埋試驗的結果之剖面SEM照片。
圖3為,表示進行使用比較例2調製之光阻下層膜形成組成物之填埋試驗的結果之剖面SEM照片。
本發明之光阻下層膜形成組成物所含有的具有上述式(1a)所表示之重覆結構單位的聚合物之結構單位如,下述式(1-1)至(1-24)所表示之結構單位,具有上述式(1b)所表示之重覆結構單位的聚合物之結構單位如,下述式(1-25)至(1-48)所表示之結構單位。
本發明之光阻下層膜形成組成物所含有的聚合物之重量平均分子量為標準聚苯乙烯換算值如1000至50000。
前述聚合物係由,磺酸化合物等之酸觸媒存在下使具有2個羥基苯基之雙酚化合物與芳香族醛或芳香 族酮進行聚合反應而合成。前述雙酚化合物如,1,3-雙[2-(4-羥基苯基)-2-丙基]苯、1,4-雙[2-(4-羥基苯基)-2-丙基]苯。前述芳香族醛如,苯甲醛、萘甲醛、蒽醛、菲醛、水楊醛、苯基乙醛、3-苯基丙醛、甲苯醛、(N,N-二甲基胺基)苯甲醛、乙醯氧苯甲醛、1-芘羧醛、茴香醛。另可取代前述芳香族醛使用例如糠醛、吡啶羧醛、噻吩羧醛般具有雜環之醛。又,前述芳香族酮為二芳香酮類,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-芴酮。前述雙酚化合物與前述芳香族醛或芳香族酮之添加比例如為1:1(莫耳比)。該添加比也可選擇1:2(莫耳比),但此時所合成之聚合物會具有前述式(1a)所表示之重覆結構單位及前述式(1b)所表示之重覆結構單位中任一種以外之結構單位。前述雙酚化合物非限定於一種化合物可使用二種以上,芳香族醛或芳香族酮非限定於一種化合物可使用二種以上。例如雙酚化合物可使用1,3-雙[2-(4-羥基苯基)-2-丙基]苯及1,4-雙[2-(4-羥基苯基)-2-丙基]苯,芳香族醛可使用苯甲醛與萘甲醛。
本發明之光阻下層膜形成組成物可另含有交聯劑。前述交聯劑較佳為使用具有至少2個交聯形成取代基之交聯性化合物。例如具有羥甲基、甲氧基甲基等之交聯形成取代基的三聚氰胺系化合物、取代尿素系化合物及苯酚系化合物。具體為甲氧基甲基化甘脲、甲氧基甲基化三聚氰胺等之化合物,例如四甲氧基甲基甘脲、四丁氧基甲基甘脲、六甲氧基甲基三聚氰胺。又,取代尿素系化合 物如,四甲氧基甲基尿素、四丁氧基甲基尿素。苯酚系化合物如,四羥基甲基雙酚、四羥基甲基雙酚、四甲氧基甲基雙酚(TMOM-BP)、四甲氧基甲基雙酚。
前述交聯劑又可使用具有至少2個環氧基之化合物。該類化合物如,三(2,3-環氧丙基)異三聚異氰酸酯、1,4-丁二醇二縮水甘油醚、1,2-環氧基-4-(環氧乙基)環己烷、甘油三縮水甘油醚、二乙二醇二縮水甘油醚、2,6-二縮水甘油基苯基縮水甘油醚、1,1,3-三[p-(2,3-環氧丙氧基)苯基]丙烷、1,2-環己烷二羧酸二縮水甘油酯、4,4’-伸甲基雙(N,N-二縮水甘油基苯胺)、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、三羥甲基乙烷三縮水甘油醚、雙酚-A-二縮水甘油醚、戴歇爾(股)製之耶波里[登記商標]GT-401、同GT-403、同GT-301、同GT-302、歇洛吉[登記商標]2021、同3000、三菱化學(股)製之1001、1002、1003、1004、1007、1009、1010、828、807、152、154、180S75、871、872、日本化藥(股)製之EPPN 201、同202、EOCN-102、同103S、同104S、同1020、同1025、同1027、那佳歇(股)製之丹那可[登記商標]EX-252、同EX-611、同EX-612、同EX-614、同EX-622、同EX-411、同EX-512、同EX-522、同EX-421、同EX-313、同EX-314、同EX-321、BASF日本(股)製之CY175、CY177、CY179、CY182、CY184、CY192、DIC(股)製之耶皮庫200、同400、同7015、同835LV、同850CRP。前述具有至少2個環氧基之化合物又可使用具有胺基之環 氧樹脂。該類環氧樹脂如,YH-434、YH-434L(東都化成(股)製)。
前述交聯劑又可使用具有至少2個嵌段異氰酸酯基之化合物。該類化合物如,三井化學(股)製之塔肯內[登記商標]B-830、同B-870N、耶泊尼公司製之VESTANAT[登記商標]B1358/100。
前述交聯劑又可使用具有至少2個乙烯醚基之化合物。該類化合物如,雙(4-(乙烯氧基甲基)環己基甲基)戊二酸酯、三(乙二醇)二乙烯醚、己二酸二乙烯醚、二乙二醇二乙烯醚、1,2,4-三(4-乙烯氧基丁基)偏苯三酸酯、1,3,5-三(4-乙烯氧基丁基)偏苯三酸酯、雙(4-(乙烯氧基)丁基)對苯二甲酸酯、雙(4-(乙烯氧基)丁基)間苯二酸酯、乙二醇二乙烯醚、1,4-丁二醇二乙烯醚、四甲二醇二乙烯醚、四乙二醇二乙烯醚、新戊二醇二乙烯醚、三羥甲基丙烷三乙烯醚、三羥甲基乙烷三乙烯醚、己二醇二乙烯醚、1,4-環己二醇二乙烯醚、四乙二醇二乙烯醚、季戊四醇二乙烯醚、季戊四醇三乙烯醚及環己烷二甲醇二乙烯醚。可由該等交聯劑中選擇一種添加,或二種以上組合添加。
前述交聯劑之含有比例相對於由本發明之光阻下層膜形成組成物去除後述溶劑所得之固體成份,例如為2質量%至60質量%。
本發明之光阻下層膜形成組成物可另含有酸性化合物。前述酸性化合物具有作為促進交聯反應用之觸媒作用,例如p-甲苯磺酸、三氟甲烷磺酸、吡啶鎓-p-甲 苯磺酸酯、水楊酸、嵌磺酸、5-磺基水楊酸、4-氯苯磺酸、4-羥基苯磺酸、苯二磺酸、1-萘磺酸、檸檬酸、苯甲酸、羥基苯甲酸等之磺酸化合物及羧酸化合物、鹽酸、硫酸、硝酸、磷酸等之無機酸。又可取代上述酸性化合物,或含有上述酸性化合物下,含有熱酸發生劑。前述熱酸發生劑也具有作為促進交聯反應用之觸媒作用,例如三氟甲烷磺酸之四級銨鹽。可由該等酸性化合物及熱酸發生劑中選擇一種添加,或二種以上組合添加。前述酸性化合物或熱酸發生劑之含有比例相對於由本發明之光阻下層膜形成組成物去除後述溶劑所得之固體成份,例如為0.1質量%至20質量%。
本發明之光阻下層膜形成組成物可另含有表面活性劑。前述表面活性劑如,聚環氧乙烷月桂酸、聚環氧乙烷硬脂醚、聚環氧乙烷十六烷醚、聚環氧乙烷油醚等之聚環氧乙烷烷基醚類、聚環氧乙烷辛基苯醚、聚環氧乙烷壬基苯醚等之聚環氧乙烷烷基芳基醚類、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之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之聚環氧乙烷山梨糖醇酐脂肪酸酯類等之陽離子系表面活性劑、耶佛特 [登記商標]EF301、同EF303、同EF352(三菱馬帖里電子化成(股)製)、美佳汎[登記商標]F171、同F173、同R-30、同R-30-N(DIC(股)製)、佛洛拉FC430、同FC431(住友3M(股)製)、阿薩西[登記商標]AG710、薩佛隆[登記商標]S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(旭硝子(股)製)等之氟系表面活性劑、有機矽氧烷聚合物KP341(信越化學工業(股)製)。可由該等表面活性劑中選擇一種添加,或二種以上組合添加。前述表面活性劑之含有比例相對於由本發明之光阻下層膜形成組成物去除後述溶劑所得之固體成份,例如為0.01質量%至5質量%。
本發明之光阻下層膜形成組成物可藉由,將上述各成份溶解於適當溶劑調製所得,其係以均勻之溶液狀態使用。該類溶劑如,乙二醇單甲基醚、乙二醇單乙基醚、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、丙二醇單丙基醚、丙二醇單甲基醚乙酸酯、丙二醇丙基醚乙酸酯、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、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、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮。該等有機溶劑可使 用一種或二種以上組合使用,由前述組成物去除有機溶劑所得之固體成份之比例如0.5質量%至30質量%,較佳為0.8質量%至15質量%。
將本發明之光阻下層膜形成組成物塗佈於具有段差、凹部及/或凸部之表面再焙燒之步驟,係藉由旋轉器、塗佈機等適當之塗佈方法將該組成物塗佈於具有段差、凹部及/或凸部之表面的基板(例如形成配線、其他結構體之矽晶圓,該矽晶圓可被氧化矽膜、氮化矽膜、氧化氮化矽膜,或鋁、鎢等之金屬膜被覆)上,其後使用熱板等之加熱方法進行焙燒之方式進行。焙燒條件可由焙燒溫度100℃至400℃、焙燒時間0.3分鐘至10分鐘之範圍內適當選擇。
於藉由前述步驟所形成之第一層之光阻下層膜上形成有機聚矽氧烷膜作為第二層之光阻下層膜,其次再於其上方形成光阻圖型。形成該光阻圖型之步驟中,曝光係藉由通過形成一定圖型用之遮罩(光罩)或直接描繪進行。曝光源例如可使用g線、i線、KrF準分子雷射、ArF準分子雷射、EUV、電子線。曝光後必要時可進行曝光後加熱(Post Exposure Bake)。其後藉由顯像液(例如2.38質量%氫氧化四甲基銨水溶液)顯像,再以清洗液或純水刷洗,以去除所使用之顯像液。其後為了使光阻圖型乾燥及提高與底層之密合性而進行後焙燒。
形成前述光阻圖型後之蝕刻步驟係藉由乾蝕進行。乾蝕所使用之蝕刻氣體相對於第二層之光阻下層膜 (有機聚矽氧烷膜)如CHF3、CF4、C2F6,又,相對於由本發明之光阻下層膜形成組成物所形成之第一層之光阻下層膜如O2、N2O、NO2,相對於具有段差或凹部及/或凸部之表面如CHF3、CF4、C2F6。另外該等氣體可混合氬、氮或二氧化碳使用。
下面將舉合成例及實施例說明本發明,但本發明非限定於下述記載。
下述合成例1及合成例2與比較合成例1及比較合成例2所示之重量平均分子量及多分散度係依據凝膠滲透色譜(以下本說明書中簡稱為GPC)之測定結果。測定時係使用東索(股)製GPC裝置,測定條件如下所述。
GPC管柱:TSKgel SuperMultipore[登記商標]Hz-N(東索(股))
管柱溫度:40℃
溶劑:四氫呋喃(THF)
流量:0.35mL/分
標準試料:聚苯乙烯(東索(股))
氮氣下將1,3-雙[2-(4-羥基苯基)-2-丙基]苯(10.00g,0.0289mol,東京化成工業(股)製)、1-芘羧醛(6.646g,0.0289mol,阿爾得公司製)及甲烷磺酸(0.5548g, 0.0058mol,東京化成工業(股)製)加入300mL四口燒瓶內,再加入丙二醇單甲基醚(7.74g,關東化學(股)製)及丙二醇單甲基醚乙酸酯(18.06g,關東化學(股)製)。攪拌前述四口燒瓶內之混合物下升溫至120℃使其溶解而開始聚合。24小時後放冷至室溫,再沈澱於甲醇(500g,關東化學(股)製)中。過濾所得之沈澱物後,於減壓乾燥機內以50℃乾燥10小時,得目的之聚合物(以下本說明書中簡稱為BPM-Py)10.82g。BPM-Py藉由GPC以聚苯乙烯換算測得之重量平均分子量Mw為6,300、多分散度Mw/Mn(Mn為數平均分子量)1.90。
氮氣下將1,4-雙[2-(4-羥基苯基)-2-丙基]苯(10.00g,0.0289mol,東京化成工業(股)製)、1-芘羧醛(6.646g,0.0289mol,阿爾得公司製)及甲烷磺酸(0.5548g,0.0058mol,東京化成工業(股)製)加入300mL四口燒瓶內,再加入丙二醇單甲基醚(7.74g,關東化學(股)製)及丙二醇單甲基醚乙酸酯(18.06g,關東化學(股)製)。攪拌前述四口燒瓶內之混合物下升溫至120℃使其溶解而開始聚合。24小時後放冷至室溫,再沈澱於甲醇(500g,關東化學(股)製)中。過濾所得之沈澱物,於減壓乾燥機內以50℃乾燥10小時,得目的之聚合物(以下本說明書中簡稱為BPP-Py)9.16g。BPP-Py藉由GPC以聚苯乙烯換算測得之重量平均分子量Mw為2,900、多分散度Mw/Mn為 2.10。
氮氣下將2,2’-雙酚(70.00g,0.3759mol,東京化成工業(股)製)、1-芘羧醛(86.559g,0.3759mol,阿爾得公司製)及甲烷磺酸(10.8389g,0.1126mol,東京化成工業(股)製)加入1000mL四口燒瓶內,再加入丙二醇單甲基醚(167.40g,關東化學(股)製)。攪拌前述四口燒瓶內之混合物下升溫至120℃使其溶解而開始聚合。24小時後放冷至室溫,再沈澱於甲醇(3000g,關東化學(股)製)中。過濾所得之沈澱物,於減壓乾燥機內以50℃乾燥10小時,得具有下述式(3)所表示之結構單位之聚合物(以下本說明書中簡稱為2,2’-BPOH-Py)84.1g。2,2’-BPOH-Py藉由GPC以聚苯乙烯換算測得之重量平均分子量Mw為1400、多分散度Mw/Mn為1.49。
氮氣下將咔唑(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)及對甲苯磺酸-水合物(0.76g,0.0040mol,東京化成工業(股)製)加入100mL四口燒瓶內,再加入1,4-二噁烷(6.69g, 關東化學(股)製)。攪拌前述四口燒瓶內之混合物下升溫至100℃使其溶解而開始聚合。24小時後放冷至60℃,再加入氯仿(34g,關東化學(股)製)稀釋,其後再沈澱於甲醇(168g,關東化學(股)製)中。過濾所得之沈澱物,於減壓乾燥機內以80℃乾燥24小時,得目的之具有下述式(4)所表示之結構單位之聚合物(以下本說明書中簡稱為PCzFL)9.37g。PCzFL藉由GPC以聚苯乙烯換算測得之重量平均分子量Mw為2800、多分散度Mw/Mn為1.77。
使合成例1所得之聚合物20g混合作為表面活性劑用之美佳汎R-30-N(DIC(股)製)0.06g後,溶解於丙二醇單甲基醚24g及丙二醇單甲基醚乙酸酯66g中得溶液。其後使用孔徑0.10μm之聚乙烯製微濾器過濾,再使用孔徑0.05μm之聚乙烯製微濾器過濾,調製微影步驟用之光阻 下層膜形成組成物。
使合成例2所得之聚合物20g混合作為表面活性劑用之美佳汎R-30-N(DIC(股)製)0.06g後,溶解於丙二醇單甲基醚24g及丙二醇單甲基醚乙酸酯66g中得溶液。其後使用孔徑0.10μm之聚乙烯製微濾器過濾,再使用孔徑0.05μm之聚乙烯製微濾器過濾,調製微影步驟用之光阻下層膜形成組成物。
使比較合成例1所得之聚合物20g混合作為表面活性劑用之美佳汎R-30(DIC(股)製)0.06g後,溶解於丙二醇單甲基醚24g及丙二醇單甲基醚乙酸酯66g中得溶液。其後使用孔徑0.10μm之聚乙烯製微濾器過濾,再使用孔徑0.05μm之聚乙烯製微濾器過濾,調製微影步驟用之光阻下層膜形成組成物。
使比較合成例2所得之聚合物20g混合作為表面活性劑用之美佳汎R-30(DIC(股)製)0.06g後,溶解於丙二醇單甲基醚乙酸酯80g中得溶液。其後使用孔徑0.10μm之聚乙烯製微濾器過濾,再使用孔徑0.05μm之聚乙烯製微濾器過濾,調製微影步驟用之光阻下層膜形成組成物。
各自使用旋轉塗佈機將實施例1及實施例2與比較例1及比較例2調製所得之光阻下層膜形成組成物塗佈於矽晶圓上。熱板上以400℃焙燒2分鐘,形成光阻下層膜(膜厚0.25μm)。將該光阻下層膜浸漬於光阻所使用之溶劑乳酸乙酯、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯及環己酮中,確認不溶於該等溶劑中。
測定乾蝕速度用之蝕刻器及蝕刻氣體為下述之物。
蝕刻器:ES401(日本賽恩提(股)製)
蝕刻氣體:CF4
各自使用旋轉塗佈機將實施例1及實施例2與比較例1及比較例2調製之光阻下層膜形成組成物塗佈於矽晶圓上。熱板上以400℃焙燒2分鐘,形成光阻下層膜(膜厚0.25μm)。蝕刻氣體係使用CF4氣體,測定該等光阻下層膜之乾蝕速度。所算出的作為乾蝕速度用由實施例1及實施例2與比較例1及比較例2調製之光阻下層膜形成組成物所形的光阻下層膜之,每單位時間(1分鐘)減少之膜厚的結果如表1所示。乾蝕速度較小時表示相對於CF4氣體之耐蝕性較高。
各自使用旋轉塗佈機將實施例1及實施例2與比較例2調製之光阻下層膜形成組成物塗佈於孔洞晶圓上。熱板上以400℃焙燒2分鐘,形成光阻下層膜(未形成孔洞部之膜厚0.25μm)。前述孔洞晶圓係使用形成直徑100nm、高400nm之孔洞圖型之晶圓。由各自如上述般塗佈實施例1及實施例2調製之光阻下層膜形成組成物再焙燒後,以掃描型電子顯微鏡(SEM)觀察各孔洞晶圓之剖面所得的圖1及圖2所示剖面SEM照片得知,光阻下層膜可充分填充至孔洞內部。另外由如上述般塗佈比較例2調製之光阻下層膜形成組成物再焙燒後,以掃描型電子顯微鏡觀察孔洞晶圓剖面所得之圖3所示剖面SEM照片得知,孔洞內部存在部份空洞。
以質量比(9:1)混合實施例1及實施例2與比較例1 及比較例2調製之光阻下層膜形成組成物,與2-羥基異丁酸甲酯,確認混合後是否有析出物。結果如表2所示。實施例1及實施例2調製之光阻下層膜形成組成物確認可溶解於2-羥基異丁酸甲酯中。另外比較例1及比較例2調製之光阻下層膜形成組成物混合2-羥基異丁酸甲酯的結果為,會生成該光阻下層膜形成組成物之析出物。
Claims (6)
- 一種光阻下層膜形成組成物,其為含有具有下述式(1a)及/或式(1b):
- 如請求項1之光阻下層膜形成組成物,其中前述聚合物為,至少一種雙酚化合物與至少一種芳香族醛或芳香族酮之聚合反應物。
- 如請求項1之光阻下層膜形成組成物,其中前述R 3所表示之芳香族烴基為苯基、萘基、蒽基或芘基。
- 如請求項1至3中任一項之光阻下層膜形成組成物,其中另含有交聯劑、酸性化合物、熱酸發生劑及表面活性劑中至少一種。
- 一種半導體裝置之製造方法,其為包含藉由將如請求項1至4中任一項之光阻下層膜形成組成物塗佈於具有段差、凹部及/或凸部之基板表面再焙燒而形成第一層之光阻下層膜的步驟、於前述第一層之光阻下層膜上形成有機聚矽氧烷膜作為第二層之光阻下層膜的步驟、於前述第二層之光阻下層膜上形成光阻圖型的步驟、以前述光阻圖型 作為遮罩蝕刻前述第二層之光阻下層膜的步驟、以蝕刻後之前述第二層之光阻下層膜的圖型作為遮罩蝕刻前述第一層之光阻下層膜的步驟,及以蝕刻後之前述第一層之光阻下層膜的圖型作為遮罩蝕刻前述具有段差、凹部及/或凸部之表面的步驟。
- 如請求項5之半導體裝置之製造方法,其中前述形成第一層之光阻下層膜的步驟及/或前述形成第二層之光阻下層膜的步驟中,另使用2-羥基異丁酸甲酯相對於前述具有段差、凹部及/或凸部之基板進行預濕處理、邊緣清洗及背面清洗。
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