TWI754683B - 抗蝕劑底層膜形成用組成物、抗蝕劑底層膜及其形成方法、經圖案化基板的製造方法及化合物 - Google Patents
抗蝕劑底層膜形成用組成物、抗蝕劑底層膜及其形成方法、經圖案化基板的製造方法及化合物 Download PDFInfo
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- TWI754683B TWI754683B TW106135861A TW106135861A TWI754683B TW I754683 B TWI754683 B TW I754683B TW 106135861 A TW106135861 A TW 106135861A TW 106135861 A TW106135861 A TW 106135861A TW I754683 B TWI754683 B TW I754683B
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Abstract
本發明是一種抗蝕劑底層膜形成用組成物,其含有:具有下述式(1)所表示的基的化合物;以及溶劑。下述式(1)中,R1
為碳數2~10的(m+n)價有機基,且具有相互鄰接的兩個碳原子,於所述兩個碳原子的其中一者上鍵結有羥基或烷氧基,於另一者上鍵結有氫原子。L1
為乙炔二基或者經取代或未經取代的乙烯二基。R2
為氫原子或碳數1~20的一價有機基。n為1~3的整數。*表示與所述化合物中的所述式(1)所表示的基以外的部分的鍵結部位。m為1~3的整數。
Description
本發明是有關於一種抗蝕劑底層膜形成用組成物、抗蝕劑底層膜及其形成方法、經圖案化基板的製造方法及化合物。
半導體元件的製造時,為了獲得高積體度而使用多層抗蝕劑製程。該製程中,首先,於基板的其中一面側塗敷膜形成用組成物後,藉由對所獲得的膜進行加熱而形成抗蝕劑底層膜,並使用抗蝕劑組成物等而於該抗蝕劑底層膜的與基板相反的面側形成抗蝕劑圖案。繼而,將該抗蝕劑圖案作為遮罩而對抗蝕劑底層膜進行蝕刻,將所獲得的抗蝕劑底層膜圖案作為遮罩,進而對基板進行蝕刻,藉此可於基板上形成所需的圖案,獲得經圖案化基板。對於所述多層抗蝕劑製程中所使用的抗蝕劑底層膜要求塗敷性優異,並且耐蝕刻性優異。
最近,於包括多種溝槽、特別是具有相互不同的縱橫比的溝槽的基板上形成圖案的情況增加。於該情況下,對於抗蝕劑底層膜的形成中所使用的抗蝕劑底層膜形成用組成物要求為可充分埋入該些溝槽者,並且具有高平坦性。
另外,最近,於多層抗蝕劑製程中,正在研究於抗蝕劑
底層膜上形成硬遮罩作為中間層的方法。該方法中,具體而言,藉由化學氣相沈積(Chemical Vapor Deposition,CVD)法於抗蝕劑底層膜上形成無機硬遮罩,因此特別是於氮化物系的無機硬遮罩的情況下,成為最低300℃、通常400℃以上的高溫,因此,抗蝕劑底層膜需要高耐熱性。若耐熱性不充分,則抗蝕劑底層膜的成分昇華,該昇華的成分再附著於基板而存在半導體元件的製造良率下降的不良情況。
針對該些要求,對抗蝕劑底層膜形成用組成物中所含有的聚合物等的結構或所包含的官能基進行了各種研究(參照日本專利特開2004-177668號公報)。但是,所述現有的抗蝕劑底層膜形成用組成物無法充分滿足該些要求。
[現有技術文獻]
[專利文獻]
[專利文獻1]日本專利特開2004-177668號公報
本發明是基於以上所述的情況而形成,其目的在於提供一種可形成發揮優異的塗敷性並且耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜的抗蝕劑底層膜形成用組成物、抗蝕劑底層膜、抗蝕劑底層膜的形成方法、經圖案化基板的製造方法及化合物。
為解決所述課題而形成的發明為一種抗蝕劑底層膜形
成用組成物,其含有:具有下述式(1)所表示的基的化合物(以下,亦稱為「[A]化合物」);以及溶劑(以下,亦稱為「[B]溶劑」)。
(式(1)中,R1為碳數2~10的(m+n)價有機基,且具有相互鄰接的兩個碳原子,於所述兩個碳原子的其中一者上鍵結有羥基或烷氧基,於另一者上鍵結有氫原子。L1為乙炔二基或者經取代或未經取代的乙烯二基。R2為氫原子或碳數1~20的一價有機基。n為1~3的整數。於n為2以上的情況下,多個L1可相同,亦可不同,多個R2可相同,亦可不同。*表示與所述[A]化合物中的所述式(1)所表示的基以外的部分的鍵結部位。m為1~3的整數)。
為解決所述課題而形成的另一發明為一種抗蝕劑底層膜,其是由該抗蝕劑底層膜形成用組成物所形成。
為解決所述課題而成的進而另一發明為一種抗蝕劑底層膜的形成方法,其包括:將該抗蝕劑底層膜形成用組成物塗敷於基板的其中一面側的步驟;以及對藉由所述塗敷步驟而獲得的塗敷膜進行加熱的步驟。
為解決所述課題而形成的進而又一發明為一種經圖案化基板的製造方法,其包括:於藉由該抗蝕劑底層膜的形成方法而獲得的抗蝕劑底層膜的與所述基板相反的面側形成抗蝕劑圖案
的步驟;以及進行以所述抗蝕劑圖案為遮罩的蝕刻的步驟。
為解決所述課題而形成的進而又一發明為一種化合物,其具有所述式(1)所表示的基。
本發明的抗蝕劑底層膜形成用組成物可形成發揮優異的塗敷性並且耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜。
本發明的抗蝕劑底層膜的耐蝕刻性、平坦性及耐熱性優異。根據本發明的抗蝕劑底層膜的形成方法,可形成發揮優異的塗敷性並且耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜。根據本發明的經圖案化基板的製造方法,可藉由使用所述形成的優異的抗蝕劑底層膜而獲得具有良好的圖案形狀的基板。本發明的化合物可較佳地用作該抗蝕劑底層膜形成用組成物的成分。因此,該些可較佳地用於今後預計進一步進行微細化的半導體元件的製造等。
1:矽基板
2:膜
a:非溝槽圖案部分
b:溝槽圖案的中央部分
△FT:溝槽圖案的中央部分b的高度與非溝槽圖案部分a的高度之差
圖1是用於說明平坦性的評價方法的示意剖面圖。
<抗蝕劑底層膜形成用組成物>
該抗蝕劑底層膜形成用組成物含有[A]化合物與[B]溶劑。該抗蝕劑底層膜形成用組成物亦可含有酸產生劑(以下,亦稱為「[C]酸產生劑」)及/或交聯劑(以下,亦稱為「[D]交聯劑」)作為較佳成分,於不損及本發明的效果的範圍內,亦可含有其他任意成分。
以下,對各成分進行說明。
<[A]化合物>
[A]化合物是具有下述式(1)所表示的基(以下,亦稱為「基(I)」)的化合物。[A]化合物可具有一個基(I),亦可具有兩個以上。[A]化合物可使用一種或兩種以上。
所述式(1)中,R1為碳數2~10的(m+n)價有機基,且具有相互鄰接的兩個碳原子,於所述兩個碳原子的其中一者上鍵結有羥基或烷氧基,於另一者上鍵結有氫原子。L1為乙炔二基或者經取代或未經取代的乙烯二基。R2為氫原子或碳數1~20的一價有機基。n為1~3的整數。於n為2以上的情況下,多個L1可相同,亦可不同,多個R2可相同,亦可不同。*表示與所述化合物中的所述式(1)所表示的基以外的部分的鍵結部位。m為1~3的整數。
該抗蝕劑底層膜形成用組成物藉由[A]化合物具有基(I),可形成發揮優異的塗敷性並且耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜。藉由該抗蝕劑底層膜形成用組成物具備所述構成而發揮所述效果的理由未必明確,但例如可如以下般進行推測。即,該抗蝕劑底層膜形成用組成物於[A]化合物的基(I)的R1中具有羥基或烷氧基,故可發揮優異的塗敷性並且使平坦性提
高。另外,R1中具有於相互鄰接的兩個碳原子上鍵結有羥基或烷氧基與氫原子的結構,故認為藉由加熱,因該羥基或烷氧基脫離的脫水反應或脫醇反應(以下,亦稱為「脫水反應等」)而生成碳-碳雙鍵,同時氧含量降低,碳含量增加,因而耐蝕刻性提高。進而認為,該生成的碳-碳雙鍵或L1的乙炔二基或乙烯二基的碳-碳多重鍵可藉由加熱而形成高密度的交聯結構,結果,耐蝕刻性及耐熱性提高。
作為R1所表示的碳數2~10的(m+n)價有機基,例如可列舉:具有相互鄰接的兩個碳原子的碳數2~10的(m+n)價烴基;該烴基的碳-碳間包含二價的含雜原子的基的基(α);以及於利用一價的含雜原子的基將所述烴基及基(α)所具有的氫原子的一部分取代而成的基(β)中,利用羥基或烷氧基將鍵結於所述烴基、基(α)及基(β)所具有的所述兩個碳原子上的氫原子中的一個取代而成基等。
作為烷氧基,例如可列舉:甲氧基、乙氧基、丙氧基、丁氧基、戊氧基等。
作為碳數2~10的(m+n)價烴基,例如可列舉自以下烴去除(m+n)個氫原子而成的基等:乙烷、丙烷、丁烷等烷烴;乙烯、丙烯、丁烯等烯烴;乙炔、丙炔、丁炔等炔烴等的碳數1~10的鏈狀烴,環戊烷、環己烷等環烷烴;
降冰片烷、金剛烷、三環癸烷等橋接環飽和烴等脂環式飽和烴;環戊烯、環己烯等環烯烴;降冰片烯、三環癸烯等橋接環不飽和烴等脂環式不飽和烴等的碳數3~10的脂環式烴;苯、甲苯、二甲苯、萘等芳烴等的碳數6~10的芳香族烴等。
作為構成含一價及二價雜原子的基的雜原子,例如可列舉:氧原子、氮原子、硫原子、磷原子、矽原子、鹵素原子等。作為鹵素原子,可列舉:氟原子、氯原子、溴原子、碘原子等。
作為二價的含雜原子的基,例如可列舉:-O-、-CO-、-S-、-CS-、-NR'-、將該些中的兩個以上組合而成的基等。R'為氫原子或一價烴基。
作為一價的含雜原子的基,例如可列舉:氟原子、氯原子、溴原子、碘原子等鹵素原子、羧基、氰基、胺基、巰基(sulfanyl)等。
作為R1,於所述式(1)中的m+n為4以下的情況下,較佳為包含下述式(A)所表示的結構(以下,亦稱為「結構(A)」)。於結構(A)中的其中一者鍵結有羥基或烷氧基、於另一者鍵結有氫原子的相互鄰接的兩個碳原子與L1的乙炔二基或乙烯二基鄰接。藉由[A]化合物具有此種結構(A),該抗蝕劑底層膜形成用組成物更容易進行脫水反應等,結果,可進一步提高耐蝕刻性及耐熱性。
所述式(A)中,RX為氫原子或碳數1~8的烷基。*1~*4中的n個表示與所述式(1)中的L1的鍵結部位,m個表示與[A]化合物中的所述基(I)以外的部分的鍵結部位。於m+n為2或3的情況下,於*1~*4中的(4-m-n)個上鍵結有氫原子或一價有機基。
較佳為於結構(A)中的*1及*2上鍵結有有機基。即,較佳為於R1的有機基中的羥基及烷氧基所鍵結的碳原子上未鍵結有氫原子。作為鍵結於*1及*2的有機基,較佳為烴基,更佳為芳香族烴基。另外,較佳為於*1及*2的至少任一者上鍵結有芳香環。作為芳香環,可列舉:苯環、萘環、蒽環、芘環等。藉由設為此種結構,可進一步提高耐蝕刻性及耐熱性。再者,於*1及*2的兩者上鍵結有有機基的情況下,該些有機基亦可與該些所鍵結的碳原子一起形成環結構。
作為RX,較佳為氫原子、甲基及乙基,更佳為氫原子及甲基,尤佳為氫原子。藉由將RX設為所述基,更容易進行脫水反應等,結果,可進一步提高耐蝕刻性及耐熱性。
作為L1所表示的乙烯二基的取代基,例如可列舉碳數1~10的一價有機基等,較佳為烴基,更佳為烷基。
作為L1,較佳為乙炔二基及未經取代的乙烯二基。
作為R2所表示的碳數1~20的一價有機基,例如可列舉:碳數1~20的一價烴基、該烴基的碳-碳間包含二價的含雜原子的基的基(α)、利用一價的含雜原子的基將所述烴基及基(α)所具有的氫原子的一部分或全部取代而成的基等。
作為R2,就耐蝕刻性及耐熱性的提高的觀點而言,較佳為氫原子及烴基,更佳為氫原子及烷基,尤佳為氫原子及甲基,特佳為氫原子。
作為n,較佳為1及2,更佳為1。
作為m,較佳為1及2,更佳為2。
作為基(I),較佳為下述式(1-1)或式(1-2)所表示的基(以下,亦稱為「基(I-1)或基(I-2)」)。基(I-1)及基(I-2)為基(I)中的R1為碳數2、且n為1、m為2或3的情況。
所述式(1-1)及式(1-2)中,R3分別獨立地為氫原子或碳數1~8的烷基。L1、R2及*與所述式(1)為相同含義。
作為R3,較佳為氫原子、甲基及乙基,更佳為氫原子及甲基,尤佳為氫原子。
作為[A]化合物中的基(I)所鍵結的部分的結構,例如
可列舉碳數1~50的有機基等。
[A]化合物中的基(I)例如可藉由以下方式來形成:使烯丙基氯化鎂等包含碳-碳雙鍵的格林納試劑(Grignard reagent)於四氫呋喃等溶劑中與具有羰基的化合物進行反應;或者使該生成物的羥基於氫化鈉等鹼存在下,於四氫呋喃等溶劑中與碘化甲基等鹵化烷基進行反應而改變為烷氧基。另外,基(I)可藉由以下方式來形成:使溴化炔丙基等包含碳-碳三重鍵的鹵化物於正丁基鋰/四甲基乙二胺等鹼存在下,於環己烷等溶劑中與具有羰基的化合物進行反應。如此,[A]化合物可由酮化合物簡便地合成。
作為[A]化合物所具有的基(I)的數量的下限,較佳為2,更佳為3。作為所述數量的上限,較佳為20,更佳為10,尤佳為4。藉由將[A]化合物中基(I)的數量設為所述範圍,可進一步提高耐蝕刻性、平坦性及耐熱性。
作為[A]化合物的氧含量的下限,較佳為3質量%,更佳為4質量%,尤佳為5質量%,特佳為6質量%。作為所述氧含量的上限,較佳為15質量%,更佳為12質量%,尤佳為10質量%,特佳為9質量%。該抗蝕劑底層膜形成用組成物藉由將[A]化合物的氧含量設為所述範圍,可進一步提高耐蝕刻性、平坦性及耐熱性。[A]化合物的「氧含量」可求出[A]化合物的結構,由該結構而算出。
[A]化合物較佳為具有芳香環。藉由[A]化合物具有芳香環,該抗蝕劑底層膜形成用組成物可進一步提高耐蝕刻性及耐熱
性。作為芳香環,可列舉:苯環、萘環、蒽環、芘環等。[A]化合物中的芳香環較佳為鍵結於所述式(1-1)中的兩個鍵結部位的至少任一者、或者所述式(1-2)中的三個鍵結部位的至少任一者。
作為[A]化合物,例如可列舉分子量為300以上、3,000以下的含芳香環的化合物(以下,亦稱為「含芳香環的化合物(I)」)、樹脂(以下,亦稱為「樹脂(I)」)等。所謂「樹脂」是指聚合物。所謂「含芳香環的化合物」是指並非聚合物的具有芳香環的化合物。以下,以含芳香環的化合物(I)、樹脂(I)的順序進行說明。
[含芳香環的化合物(I)]
含芳香環的化合物(I)為具有基(I)及芳香環,分子量為300以上、3,000以下的化合物。於含芳香環的化合物(I)具有分子量分佈的情況下,含芳香環的化合物(I)的分子量例如是藉由凝膠滲透層析法(Gel Permeation Chromatography,GPC)的聚苯乙烯換算重量平均分子量(Mw)。
作為含芳香環的化合物(I),例如可列舉下述式(i)所表示的化合物等。
所述式(i)中,Z為m為2的基(I)。Ar1為經取代或未經取代的去除碳數6~50的芳香族烴的芳香環上的k個氫原子
而成的基。Ar2為經取代或未經取代的碳數6~50的芳基。k為1~10的整數。於k為2以上的情況下,多個Z可相同,亦可不同,多個Ar2可相同,亦可不同。Ar1與一個或多個Ar2可相互鍵結。
作為提供Ar1所表示的基的碳數6~50的芳香族烴,例如可列舉:苯、萘、蒽、菲、芘、稠四苯、、稠五苯、稠六苯、蔻、聯三伸萘(trinaphthylene)、庚芬(heptaphene)、卵苯(ovalene)、戊搭烯(pentalene)、茚、薁、庚搭烯(heptalene)、伸聯苯、二環戊二烯并苯、乙烯合萘、茀、萉、醋蒽烯(aceanthrylene)、苝、苉(picene)、四伸苯(tetraphenylene)、己芬(hexaphene)、玉紅省(rubicene)、庚芬(heptaphene)、吡蒽(pyranthrene)、六螺烯(hexahelicene)等。該些中,較佳為苯、芘及蔻。
作為Ar2所表示的芳基,可列舉自作為提供所述Ar1的芳香族烴而例示者中去除芳香環上的一個氫原子而成的基等。該些中,較佳為苯基、萘基及芘基。
作為芳香族烴基的取代基,例如可列舉:羥基、鹵素原子、烷氧基、硝基、氰基、羧基等。就耐蝕刻性及耐熱性的觀點而言,較佳為芳香族烴基不具有取代基。再者,芳香族烴基的取代基亦可為所述基(I)。
作為k的下限,較佳為2,更佳為3。作為k的上限,較佳為6,更佳為4。
作為含芳香環的化合物(I)的分子量的下限,較佳為350,更佳為400。作為所述分子量的上限,較佳為2,000,更佳為
1,000,尤佳為800。藉由將含芳香環的化合物(I)的分子量設為所述範圍,可進一步提高該抗蝕劑底層膜形成用組成物的平坦性。
[樹脂(I)]
樹脂(I)為具有基(I)的樹脂。作為樹脂(I),可列舉於主鏈具有芳香環的樹脂、於主鏈不具有芳香環而於側鏈具有芳香環的樹脂等。此處,所謂「主鏈」是指包含[A]化合物中的原子的鏈中最長者。所謂「側鏈」是指包含[A]化合物中的原子的鏈中最長鏈以外者。樹脂(I)通常為具有多個基(I)的化合物。
樹脂(I)例如可將如下樹脂作為原料,並藉由段落0041中記載的方法來合成,所述樹脂具有鍵結有甲醯基等包含羰基的基的芳香環。
作為樹脂(I)的Mw的下限,較佳為500,更佳為1,000。另外,作為所述Mw的上限,較佳為50,000,更佳為10,000,尤佳為8,000。
作為樹脂(I)的Mw/Mn的下限,通常為1,較佳為1.1。作為所述Mw/Mn的上限,較佳為5,更佳為3,尤佳為2。
藉由將樹脂(I)的Mw及Mw/Mn設為所述範圍,可進一步提高該抗蝕劑底層膜形成用組成物的平坦性及表面塗敷性。
關於[A]化合物,作為含芳香環的化合物(I),例如可列舉下述式(i-1)~式(i-4)所表示的化合物等,作為樹脂(I),例如可列舉具有下述式(p-1)或式(p-2)所表示的結構單元的樹脂等。下述式(i-4)中的-Ar1'-Z1-Ar1'-對應於所述式(i)中的Ar1
的經取代的去除碳數6~50的芳香族烴的芳香環上的兩個氫原子而成的基。
所述式(i-1)~式(i-4)及式(p-1)中,Z1分別獨立地為m為2,R1由所述式(1-1)表示的情況下的基(I)。
所述式(p-2)中,Z2為m為1,R1為所述式(1-1)的情況下的基(I)。
所述式(i-1)中,Ar1A為經取代或未經取代的去除碳數
6~50的芳香族烴的芳香環上的6個氫原子而成的基。Ar2A分別獨立地為經取代或未經取代的去除碳數6~50的芳香族烴的芳香環上的兩個氫原子而成的基。作為Ar1A,較佳為苯六基(benzenehexayl)。作為Ar2A,較佳為苯二基。
所述式(i-2)中,Ar1B為經取代或未經取代的去除碳數6~50的芳香族烴的芳香環上的3個氫原子而成的基。Ar2B分別獨立地為經取代或未經取代的碳數6~50的芳基。作為Ar1B,較佳為苯三基。作為Ar2B,較佳為萘基。
所述式(i-3)中,Ar1C為經取代或未經取代的去除碳數6~50的芳香族烴的芳香環上的兩個氫原子而成的基。Ar2C分別獨立地為經取代或未經取代的碳數6~50的芳基。作為Ar1C,較佳為苯二基及蔻二基。作為Ar2C,較佳為萘基及芘基。
所述式(i-4)中,Ar1'分別獨立地為經取代或未經取代的去除碳數6~20的芳香族烴的芳香環上的兩個氫原子而成的基。Ar2D分別獨立地為經取代或未經取代的碳數6~50的芳基。作為Ar1',較佳為芘二基。作為Ar2D,較佳為苯基。
所述式(p-1)中,Ara為經取代或未經取代的去除碳數6~50的芳香族烴的4個氫原子而成的結構。作為Ara,較佳為自苊-基-聯苯去除4個氫原子而成的結構。
所述式(p-2)中,Arb為經取代或未經取代的去除碳數6~50的芳香族烴的3個氫原子而成的結構。作為Arb,較佳為自苊去除3個氫原子而成的結構。
相對於該抗蝕劑底層膜形成用組成物的所有固體成分,[A]化合物的含量的下限較佳為70質量%,更佳為80質量%,尤佳為85質量%。所述含量的上限例如為100質量%。所謂「所有固體成分」是指該抗蝕劑底層膜形成用組成物中的[B]溶劑以外的成分的總和。
作為該抗蝕劑底層膜形成用組成物中的[A]化合物的含量的下限,較佳為1質量%,更佳為3質量%,尤佳為5質量%。作為所述含量的上限,較佳為50質量%,更佳為30質量%,尤佳為15質量%。
<[B]溶劑>
[B]溶劑若可將[A]化合物及視需要含有的任意成分溶解或分散,則並無特別限定。
作為[B]溶劑,例如可列舉:醇系溶劑、酮系溶劑、醚系溶劑、酯系溶劑、含氮系溶劑等。[B]溶劑可單獨使用一種或將兩種以上組合使用。
作為醇系溶劑,例如可列舉: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、3-庚醇、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、第二-十一烷醇、三甲基壬醇、第二-十四烷醇、第二-十七烷醇、苯酚、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、二丙酮醇、甲酚等單醇系溶劑;乙二醇、1,2-丙二醇、1,3-丁二醇、2,4-戊二醇、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、甘油等多元醇系溶劑等。
作為酮系溶劑,例如可列舉: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(fenchone)等。
作為醚系溶劑,例如可列舉: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、2-甲氧基乙醇、2-乙氧基乙醇、乙二醇二乙醚、2-正丁氧基乙醇、2-正己氧基乙醇、2-苯氧基乙醇、2-(2-乙基丁氧基)乙醇、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、四乙二醇二-正丁醚、1-正丁氧基-2-丙醇、1-苯氧基-2-丙醇、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單丙醚、三丙二醇單甲醚、四氫呋喃、2-甲基四氫呋喃等。
作為酯系溶劑,例如可列舉: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、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單-正丁醚乙酸酯、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、二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、甘醇二乙酸酯、甲氧基三甘醇乙酸酯、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、鄰苯二甲酸二甲酯、鄰苯二甲酸二乙酯等。
作為含氮系溶劑,例如可列舉: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-甲基吡咯啶酮等。
該些中,較佳為醚系溶劑及酯系溶劑,就成膜性優異的觀點而言,更佳為具有二醇結構的醚系溶劑及酯系溶劑。
作為具有二醇結構的醚系溶劑及酯系溶劑,例如可列舉:丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、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等。該些中,特佳為丙二醇單甲醚乙酸酯。
作為[B]溶劑中的具有二醇結構的醚系溶劑及酯系溶劑
的含有率的下限,較佳為20質量%,更佳為60質量%,尤佳為90質量%,特佳為100質量%。
<[C]酸產生劑>
[C]酸產生劑是藉由熱或光的作用而產生酸,來促進[A]化合物的交聯的成分。藉由該抗蝕劑底層膜形成用組成物含有[C]酸產生劑,[A]化合物的交聯反應得到促進,可進一步提高所形成的膜的硬度。[C]酸產生劑可單獨使用一種或將兩種以上組合使用。
作為[C]酸產生劑,例如可列舉鎓鹽化合物、N-磺醯氧基醯亞胺化合物等。
作為所述鎓鹽化合物,例如可列舉:鋶鹽、四氫噻吩鎓鹽、錪鹽、銨鹽等。
作為鋶鹽,例如可列舉:三苯基鋶三氟甲磺酸鹽、三苯基鋶九氟-正丁磺酸鹽、三苯基鋶全氟-正辛磺酸鹽、三苯基鋶2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽、4-環己基苯基二苯基鋶三氟甲磺酸鹽、4-環己基苯基二苯基鋶九氟-正丁磺酸鹽、4-環己基苯基二苯基鋶全氟-正辛磺酸鹽、4-環己基苯基二苯基鋶2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽、4-甲磺醯基苯基二苯基鋶三氟甲磺酸鹽、4-甲磺醯基苯基二苯基鋶九氟-正丁磺酸鹽、4-甲磺醯基苯基二苯基鋶全氟-正辛磺酸鹽、4-甲磺醯基苯基二苯基鋶2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽等。
作為四氫噻吩鎓鹽,例如可列舉:1-(4-正丁氧基萘-1-基)四氫噻吩鎓三氟甲磺酸鹽、1-(4-正丁氧基萘-1-基)四氫噻吩鎓
九氟-正丁磺酸鹽、1-(4-正丁氧基萘-1-基)四氫噻吩鎓全氟-正辛磺酸鹽、1-(4-正丁氧基萘-1-基)四氫噻吩鎓2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽、1-(6-正丁氧基萘-2-基)四氫噻吩鎓三氟甲磺酸鹽、1-(6-正丁氧基萘-2-基)四氫噻吩鎓九氟-正丁磺酸鹽、1-(6-正丁氧基萘-2-基)四氫噻吩鎓全氟-正辛磺酸鹽、1-(6-正丁氧基萘-2-基)四氫噻吩鎓2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽、1-(3,5-二甲基-4-羥基苯基)四氫噻吩鎓三氟甲磺酸鹽、1-(3,5-二甲基-4-羥基苯基)四氫噻吩鎓九氟-正丁磺酸鹽、1-(3,5-二甲基-4-羥基苯基)四氫噻吩鎓全氟-正辛磺酸鹽、1-(3,5-二甲基-4-羥基苯基)四氫噻吩鎓2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽等。
作為錪鹽,例如可列舉:二苯基錪三氟甲磺酸鹽、二苯基錪九氟-正丁磺酸鹽、二苯基錪全氟-正辛磺酸鹽、二苯基錪2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽、雙(4-第三丁基苯基)錪三氟甲磺酸鹽、雙(4-第三丁基苯基)錪九氟-正丁磺酸鹽、雙(4-第三丁基苯基)錪全氟-正辛磺酸鹽、雙(4-第三丁基苯基)錪2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽等。
作為銨鹽,例如可列舉:三乙基銨三氟甲磺酸鹽、三乙基銨九氟-正丁磺酸鹽、三甲基銨九氟-正丁磺酸鹽、四乙基銨九氟-正丁磺酸鹽、三乙基銨全氟-正辛磺酸鹽、三乙基銨2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺酸鹽等。
作為N-磺醯氧基醯亞胺化合物,例如可列舉:N-(三氟甲磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(九氟-正丁
磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(全氟-正辛磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(2-雙環[2.2.1]庚-2-基-1,1,2,2-四氟乙磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺等。
該些中,作為[C]酸產生劑,較佳為鎓鹽化合物,更佳為錪鹽及銨鹽,尤佳為雙(4-第三丁基苯基)錪九氟-正丁磺酸鹽及三乙基銨九氟-正丁磺酸鹽。
於該抗蝕劑底層膜形成用組成物含有[C]酸產生劑的情況下,相對於[A]化合物100質量份,[C]酸產生劑的含量的下限較佳為0.1質量份,更佳為1質量份,尤佳為3質量份。作為所述含量的上限,較佳為20質量份,更佳為15質量份,尤佳為12質量份。藉由將[C]酸產生劑的含量設為所述範圍,可更有效地促進[A]化合物的交聯反應。
[[D]交聯劑]
[D]交聯劑是藉由熱或酸的作用,而形成該抗蝕劑底層膜形成用組成物中的[A]化合物等成分彼此的交聯鍵或該些自身形成交聯結構的成分。藉由該抗蝕劑底層膜形成用組成物含有[D]交聯劑,可提高所形成的膜的硬度。[D]交聯劑可單獨使用一種或者組合使用兩種以上。
作為[D]交聯劑,例如可列舉:多官能(甲基)丙烯酸酯化合物、環氧化合物、羥基甲基取代的酚化合物、含烷氧基烷基的酚化合物、具有經烷氧基烷基化的胺基的化合物、下述式(11-P)
所表示的乙烯合萘與羥基甲基乙烯合萘的無規共聚物、下述式(11-1)~式(11-12)所表示的化合物等。
作為所述多官能(甲基)丙烯酸酯化合物,例如可列舉:三羥甲基丙烷三(甲基)丙烯酸酯、二-三羥甲基丙烷四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、三(2-羥基乙基)異氰脲酸酯三(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、雙(2-羥基乙基)異氰脲酸酯二(甲基)丙烯酸酯等。
作為所述環氧化合物,例如可列舉:酚醛清漆型環氧樹脂、雙酚型環氧樹脂、脂環式環氧樹脂、脂肪族環氧樹脂等。
作為所述羥基甲基取代的酚化合物,例如可列舉:2-羥基甲基-4,6-二甲基苯酚、1,3,5-三羥基甲基苯、3,5-二羥基甲基-4-甲氧基甲苯[2,6-雙(羥基甲基)-對甲酚]等。
作為所述含烷氧基烷基的酚化合物,例如可列舉:含甲氧基甲基的酚化合物、含乙氧基甲基的酚化合物等。
作為所述具有經烷氧基烷基化的胺基的化合物,例如可列舉(聚)羥甲基化三聚氰胺、(聚)羥甲基化甘脲、(聚)羥甲基化苯并胍胺、(聚)羥甲基化脲等在一分子內具有多個活性羥甲基的含氮
化合物,且所述羥甲基的羥基的氫原子的至少一個經甲基或丁基等烷基所取代的化合物等。此外,具有經烷氧基烷基化的胺基的化合物可為將多種取代化合物混合而成的混合物,亦可為包含一部分自縮合而成的寡聚物成分者。
所述式(11-6)、式(11-8)、式(11-11)及式(11-12)中,Ac表示乙醯基。
再者,所述式(11-1)~式(11-12)所表示的化合物分別可參考以下的文獻來合成。
式(11-1)所表示的化合物:郭群生(Guo,Qun-Sheng)、盧永娜(Lu,Yong-Na)、劉兵(Liu,Bing)、肖健(Xiao,Jian)、李金山(Li,Jin-Shan),「有機金屬化學雜誌(Journal of Organometallic Chemistry)」,2006年第691卷第6期第1282-1287頁
式(11-2)所表示的化合物:巴達,Y.(Badar,Y.)等人的「化學學會會刊(Journal of the Chemical Society)」,1965年第1412-1418頁
式(11-3)所表示的化合物:謝仁傑(Hsieh,Jen-Chieh)、鄭建鴻(Cheng,Chien-Hong),「化學通訊(Chemical Communications)」(劍橋(Cambridge),英國(United Kingdom)),2008年第26期第2992-2994頁
式(11-4)所表示的化合物:日本專利特開平5-238990號公報
式(11-5)所表示的化合物:
培根,R.G.R.(Bacon,R.G.R.)、班克赫德,R.(Bankhead,R.),「化學學會會刊(Journal of the Chemical Society)」,1963年第839-845頁
式(11-6)、式(11-8)、式(11-11)及式(11-12)所表示的化合物:「巨分子(Macromolecules)」,2010年第43卷第2832-2839頁
式(11-7)、式(11-9)及式(11-10)所表示的化合物:「聚合物雜誌(Polymer Journal)」2008年第40卷第7期第645-650頁、以及「聚合物科學雜誌:A輯,聚合物化學(Journal of Polymer Science:Part A,Polymer Chemistry)」第46卷第4949-4958頁
該些[D]交聯劑中,較佳為含甲氧基甲基的酚化合物、具有經烷氧基烷基化的胺基的化合物以及乙烯合萘與羥基甲基乙烯合萘的無規共聚物,更佳為具有經烷氧基烷基化的胺基的化合物,尤佳為1,3,4,6-四(甲氧基甲基)甘脲。
於該抗蝕劑底層膜形成用組成物含有[D]交聯劑的情況下,相對於[A]化合物100質量份,[D]交聯劑的含量的下限較佳為0.1質量份,更佳為0.5質量份,尤佳為1質量份,特佳為3質量份。作為所述含量的上限,較佳為100質量份,更佳為50質量份,尤佳為30質量份,特佳為20質量份。藉由將[D]交聯劑的含量設為所述範圍,可更有效地引起[A]化合物的交聯反應。
<其他任意成分>
作為其他任意成分,例如可列舉界面活性劑等。
[界面活性劑]
該抗蝕劑底層膜形成用組成物可藉由含有界面活性劑而提高塗敷性,其結果,所形成的膜的塗敷面均勻性提高,且可抑制塗敷不均的產生。界面活性劑可單獨使用一種或將兩種以上組合使用。
作為界面活性劑,例如可列舉:聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯油烯基醚、聚氧乙烯-正辛基苯基醚、聚氧乙烯-正壬基苯基醚、聚乙二醇二月桂酸酯、聚乙二醇二硬脂酸酯等非離子系界面活性劑等。另外,作為市售品,可列舉:KP341(信越化學工業公司),珀利弗洛(Polyflow)No.75、珀利弗洛(Polyflow)No.95(以上,共榮社油脂化學工業公司),艾福拓(Eftop)EF101、艾福拓(Eftop)EF204、艾福拓(Eftop)EF303、艾福拓(Eftop)EF352(以上,托克姆產品(Tochem Products)公司),美佳法(Megafac)F171、美佳法(Megafac)F172、美佳法(Megafac)F173(以上,迪愛生(DIC)公司),弗拉德(Fluorad)FC430、弗拉德(Fluorad)FC431、弗拉德(Fluorad)FC135、弗拉德(Fluorad)FC93(以上,住友3M公司),阿薩佳(Asahi Guard)AG710、沙福隆(Surflon)S382、沙福隆(Surflon)SC101、沙福隆(Surflon)SC102、沙福隆(Surflon)SC103、沙福隆(Surflon)SC104、沙福隆(Surflon)SC105、沙福隆(Surflon)SC106(以
上,旭硝子公司)等。
於該抗蝕劑底層膜形成用組成物含有界面活性劑的情況下,相對於[A]化合物100質量份,界面活性劑的含量的下限較佳為0.01質量份,更佳為0.05質量份,尤佳為0.1質量份。作為所述含量的上限,較佳為10質量份,更佳為5質量份,尤佳為1質量份。藉由將界面活性劑的含量設為所述範圍,可進一步提高該抗蝕劑底層膜形成用組成物的塗敷性。
<抗蝕劑底層膜形成用組成物的製備方法>
該抗蝕劑底層膜形成用組成物可藉由將[A]化合物、[B]溶劑、視需要的[C]酸產生劑、[D]交聯劑及其他的任意成分以既定的比例進行混合,較佳為利用0.1μm左右的薄膜過濾器等將所獲得的混合物進行過濾而製備。作為該抗蝕劑底層膜形成用組成物的固體成分濃度的下限,較佳為0.1質量%,更佳為1質量%,尤佳為3質量%,特佳為5質量%。作為所述固體成分濃度的上限,較佳為50質量%,更佳為30質量%,尤佳為20質量%,特佳為15質量%。
該抗蝕劑底層膜形成用組成物可形成塗敷性優異且耐蝕刻性、平坦性及耐熱性優異的膜,故可較佳地用以形成半導體元件的製造等中的抗蝕劑底層膜。另外,亦可用以形成顯示元件等中的保護膜、絕緣膜、著色硬化膜。
<抗蝕劑底層膜>
本發明的抗蝕劑底層膜是由該抗蝕劑底層膜形成用組成物所
形成。該抗蝕劑底層膜由具有所述特性的該抗蝕劑底層膜形成用組成物所形成,故耐蝕刻性、平坦性及耐熱性優異。
<抗蝕劑底層膜的形成方法>
該抗蝕劑底層膜的形成方法包括:將該抗蝕劑底層膜形成用組成物塗敷於基板的其中一面側的步驟(以下,亦稱為「塗敷步驟」);以及對藉由所述塗敷步驟而獲得的塗敷膜進行加熱的步驟(以下,亦稱為「加熱步驟」)。根據該抗蝕劑底層膜的形成方法,使用具有所述特性的抗蝕劑底層膜形成用組成物,故可形成耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜。
[塗敷步驟]
本步驟中,將該抗蝕劑底層膜形成用組成物塗敷於基板的其中一面側。
作為基板,例如可列舉矽晶圓、由鋁被覆的晶圓等。另外,該抗蝕劑底層膜形成用組成物的塗敷方法並無特別限定,例如可利用旋轉塗敷、流延塗敷、輥塗敷等適當的方法來實施,藉此可形成塗膜。
[加熱步驟]
本步驟中,對藉由所述塗敷步驟而獲得的塗敷膜進行加熱。藉此形成抗蝕劑底層膜。
所述塗敷膜的加熱通常於大氣下進行。作為加熱溫度的下限,較佳為150℃,更佳為200℃,尤佳為250℃。作為加熱溫
度的上限,較佳為500℃,更佳為450℃,尤佳為400℃。於加熱溫度小於150℃的情況下,氧化交聯不會充分進行,存在不會表現出作為抗蝕劑底層膜而必需的特性的顧慮。作為加熱時間的下限,較佳為15秒,更佳為30秒,尤佳為45秒。作為加熱時間的上限,較佳為1,200秒,更佳為600秒,尤佳為300秒。
對所述塗敷膜於150℃以上、500℃以下的溫度下進行加熱之前,亦可於60℃以上、250℃以下的溫度下進行預加熱。作為預加熱中的加熱時間的下限,較佳為10秒,更佳為30秒。作為所述加熱時間的上限,較佳為300秒,更佳為180秒。藉由進行該預加熱,使溶劑預先氣化而使膜緻密,藉此可高效率地進行於後述的加熱時引起的脫氫反應。
再者,於該抗蝕劑底層膜的形成方法中,對所述塗敷膜進行加熱而形成抗蝕劑底層膜,於該抗蝕劑底層膜形成用組成物含有[C]酸產生劑且[C]酸產生劑為感放射線性酸產生劑的情況下,亦可藉由將曝光與加熱加以組合而使膜硬化,來形成抗蝕劑底層膜。作為該曝光中所使用的放射線,可根據[C]酸產生劑的種類而自可見光線、紫外線、遠紫外線、X射線、γ射線等電磁波;電子束、分子束、離子束等粒子束中適當選擇。
作為所形成的抗蝕劑底層膜的平均厚度的下限,較佳為50nm,更佳為100nm,尤佳為200nm。作為所述平均厚度的上限,較佳為3,000nm,更佳為2,000nm,尤佳為500nm。
<經圖案化基板的製造方法>
本發明的經圖案化基板的製造方法包括:於藉由該抗蝕劑底層膜的形成方法而獲得的抗蝕劑底層膜的與所述基板相反的面側形成抗蝕劑圖案的步驟(以下,亦稱為「抗蝕劑圖案形成步驟」);及進行以所述抗蝕劑圖案為遮罩的蝕刻的步驟(以下,亦稱為「蝕刻步驟」)。
根據該經圖案化基板的製造方法,使用藉由所述該抗蝕劑底層膜的形成方法而獲得的耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜,故可獲得具有優異的圖案形狀的經圖案化基板。
該經圖案化基板的製造方法於抗蝕劑圖案形成步驟之前,視需要亦可包括於所述抗蝕劑底層膜的與基板相反的面側形成中間層(中間膜)的步驟。以下,對各步驟進行說明。
[中間層形成步驟]
本步驟中,於所述抗蝕劑底層膜的與基板相反的面側形成中間層。該中間層是為了於抗蝕劑圖案形成中,對抗蝕劑底層膜及/或抗蝕劑膜所具有的功能進行進一步補充,或者提供該些膜所不具有的功能而賦予所述功能的層。例如,於形成抗反射膜作為中間層的情況下,可進一步補充抗蝕劑底層膜的抗反射功能。
該中間層可利用有機化合物或無機氧化物來形成。關於所述有機化合物,作為市售品,例如可列舉:「DUV-42」、「DUV-44」、「ARC-28」、「ARC-29」(以上為布魯爾科技(Brewer Science)公司);「AR-3」、「AR-19」(以上為羅門哈斯(Rohm and Haas)公司)等。關於所述無機氧化物,作為市售品,例如可列
舉:「NFC SOG01」、「NFC SOG04」、「NFC SOG080」(以上為日本合成橡膠(Japan Synthetic Rubber,JSR)公司)等。另外,作為所述無機氧化物,可使用藉由CVD法而形成的聚矽氧烷、氧化鈦、氧化鋁、氧化鎢等。
中間層的形成方法並無特別限定,例如可使用塗敷法或CVD法等。該些中,較佳為塗敷法。於使用塗敷法的情況下,可於形成抗蝕劑底層膜後,連續地形成中間層。另外,中間層的平均厚度可根據中間層所要求的功能來適當選擇,作為中間層的平均厚度的下限,較佳為10nm,更佳為20nm。作為所述平均厚度的上限,較佳為3,000nm,更佳為300nm。
[抗蝕劑圖案形成步驟]
本步驟中,於所述抗蝕劑底層膜的與基板相反的面側形成抗蝕劑圖案。於進行所述中間層形成步驟的情況下,於中間層的與基板相反的面側形成抗蝕劑圖案。作為進行該步驟的方法,例如可列舉使用抗蝕劑組成物的方法等。
使用所述抗蝕劑組成物的方法中,具體而言,以所獲得的抗蝕劑膜成為既定厚度的方式塗敷抗蝕劑組成物後,藉由進行預烘烤而使塗膜中的溶劑揮發,藉此形成抗蝕劑膜。
作為所述抗蝕劑組成物,例如可列舉:含有感放射線性酸產生劑的正型或負型的化學增幅型抗蝕劑組成物、含有鹼可溶性樹脂與醌二疊氮化物系感光劑的正型抗蝕劑組成物、含有鹼可溶性樹脂與交聯劑的負型抗蝕劑組成物等。
作為所述抗蝕劑組成物的固體成分濃度的下限,較佳為0.3質量%,更佳為1質量%。作為所述固體成分濃度的上限,較佳為50質量%,更佳為30質量%。另外,所述抗蝕劑組成物通常利用例如孔徑0.2μm左右的過濾器進行過濾而提供給抗蝕劑膜的形成。再者,該步驟中,亦可直接使用市售的抗蝕劑組成物。
作為抗蝕劑組成物的塗敷方法,並無特別限定,例如可列舉旋轉塗佈法等。另外,作為預烘烤的溫度,可根據所使用的抗蝕劑組成物的種類等而適當調整,作為所述溫度的下限,較佳為30℃,更佳為50℃。作為所述溫度的上限,較佳為200℃,更佳為150℃。作為預烘烤的時間的下限,較佳為10秒,更佳為30秒。作為所述時間的上限,較佳為600秒,更佳為300秒。
其次,藉由選擇性的放射線照射而對所述形成的抗蝕劑膜進行曝光。作為曝光中所使用的放射線,可根據抗蝕劑組成物中所使用的感放射線性酸產生劑的種類,而自可見光線、紫外線、遠紫外線、X射線、γ射線等電磁波;電子束、分子束、離子束等粒子束中適當選擇。該些中,較佳為遠紫外線,更佳為KrF準分子雷射光(248nm)、ArF準分子雷射光(193nm)、F2準分子雷射光(波長157nm)、Kr2準分子雷射光(波長147nm)、ArKr準分子雷射光(波長134nm)及極紫外線(波長13.5nm等,(Extreme Ultraviolet,EUV)),尤佳為KrF準分子雷射光、ArF準分子雷射光及EUV。
於所述曝光後,為了提高解析度、圖案輪廓、顯影性等,
可進行後烘烤。作為該後烘烤的溫度,可根據所使用的抗蝕劑組成物的種類等而適當調整,作為所述溫度的下限,較佳為50℃,更佳為70℃。作為所述溫度的上限,較佳為200℃,更佳為150℃。作為後烘烤的時間的下限,較佳為10秒,更佳為30秒。作為所述時間的上限,較佳為600秒,更佳為300秒。
其次,利用顯影液對所述經曝光的抗蝕劑膜進行顯影而形成抗蝕劑圖案。該顯影可為鹼顯影,亦可為有機溶劑顯影。作為顯影液,於鹼顯影的情況下,例如可列舉:氫氧化鈉、氫氧化鉀、碳酸鈉、矽酸鈉、偏矽酸鈉、氨、乙基胺、正丙基胺、二乙基胺、二-正丙基胺、三乙基胺、甲基二乙基胺、二甲基乙醇胺、三乙醇胺、氫氧化四甲基銨、氫氧化四乙基銨、吡咯、哌啶、膽鹼、1,8-二氮雜雙環[5.4.0]-7-十一烯、1,5-二氮雜雙環[4.3.0]-5-壬烯等的鹼性水溶液。該些鹼性水溶液中亦可添加適量的例如甲醇、乙醇等醇類等水溶性有機溶劑、界面活性劑等。另外,於有機溶劑顯影的情況下,作為顯影液,例如可列舉所述的作為抗蝕劑底層膜形成用組成物的[B]溶劑而例示的多種有機溶劑等。
於利用所述顯影液的顯影後,藉由進行洗滌、乾燥而形成既定的抗蝕劑圖案。
作為進行抗蝕劑圖案形成步驟的方法,除了所述的使用抗蝕劑組成物的方法以外,亦可使用利用奈米壓印法的方法、利用自組織化組成物的方法等。
[蝕刻步驟]
本步驟中,進行以所述抗蝕劑圖案為遮罩的蝕刻。藉此於基板上形成圖案。作為蝕刻的次數,可為一次,亦可為多次,即,將藉由蝕刻而獲得的圖案作為遮罩來依序進行蝕刻,就獲得更良好的形狀的圖案的觀點而言,較佳為多次。當進行多次蝕刻時,於不具有所述中間層的情況下,以抗蝕劑底層膜、基板的順序依序進行蝕刻,於具有所述中間層的情況下,以中間層、抗蝕劑底層膜、基板的順序依序進行蝕刻。作為蝕刻的方法,可列舉乾式蝕刻、濕式蝕刻等。該些中,就使基板的圖案的形狀更良好的觀點而言,較佳為乾式蝕刻。該乾式蝕刻中使用例如氧電漿等氣體電漿等。於所述蝕刻後,獲得具有既定圖案的經圖案化基板。
<化合物>
該化合物為具有所述基(I)的化合物。該化合物具有所述性質,故可較佳地用作該抗蝕劑底層膜形成用組成物的成分。該化合物於該抗蝕劑底層膜形成用組成物的項中作為[A]化合進行說明。
[實施例]
以下,藉由實施例來對本發明進一步進行具體說明,但本發明並不限定於該些實施例。以下示出各種物性值的測定方法。
[Mw及Mn]
[A]化合物為樹脂時的Mw及Mn是使用東曹(Tosoh)公司的凝膠滲透層析(GPC)管柱(兩根「G2000HXL」及一根「G3000HXL」),以流量:1.0mL/min、溶出溶劑:四氫呋喃、管
柱溫度:40℃的分析條件,利用以單分散聚苯乙烯為標準的凝膠滲透層析儀(檢測器:示差折射計)來測定。
[膜的平均厚度]
膜的平均厚度是使用分光橢圓偏振計(J.A.沃蘭姆(J.A.WOOLLAM)公司的「M2000D」)來測定。
<[A]化合物的合成>
藉由以下所示的順序來合成下述式(A-1)~式(A-10)所表示的化合物。再者,表1中記載的[A]化合物的氧含量為根據化合物的結構算出的值。
化合物(A-1)、化合物(A-9)及化合物(A-10)分別為具有所述式所表示的結構單元的樹脂。
[實施例1-1]
於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下加入23.63g的苊醌、20.0g的聯苯及130g的二氯甲烷,使其溶解。繼而,添加17.75g的三氟乙酸及23.36g的三氟甲磺酸,於20℃下攪拌12小時而進行聚合。然後,將聚合反應液投入至大量的甲醇中,對沈澱的樹脂進行過濾後,於60℃下減壓乾燥一晚,獲得下述式(B-1)所表示的樹脂。其次,於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下加入40g的樹脂(B-1)及120g的四氫呋喃,於室溫下使其溶解。冷卻至0℃後,歷時0.5小時來滴加155g的烯丙基氯化鎂的四氫呋喃溶液(1M)。滴加結束後,加溫至60℃而進行3小時反應。反應結束後,將反應液添加於大量的水中後,添加120g的甲基異丁基酮而進行萃取。針對所獲得的有機層,實施兩次水洗後,投入至600g的己烷中而進行再沈澱。將所獲得的沈澱物濾出後,於60℃下減壓乾燥一晚,藉此而獲得所述化合物(A-1)(產率78%)。化合物(A-1)的Mw為1,500。
[實施例1-2]
於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下加入15g的下述式(B-2)所表示的化合物及120g的四氫呋喃,於室溫下使其溶解。冷卻至0℃後,歷時0.5小時來滴加155g的烯丙基氯化鎂的四氫呋喃溶液(1M)。滴加結束後,加溫至60℃而進行3小時反應。反應結束後,將反應液添加於大量的水中後,添加120g的甲基異丁基酮而進行萃取。針對所獲得的有機層,實施兩次水洗後,投入至600g的己烷中而進行再沈澱。將所獲得的沈澱物濾出後,於60℃下減壓乾燥一晚,藉此而獲得所述化合物(A-2)(產率80%)。
[實施例1-3]
於實施例1-2中,使用下述式(B-3)所表示的化合物來代替化合物(B-2),除此以外與實施例1-2同樣地進行來合成所述化合物(A-3)。
[實施例1-4]
於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,
於氮氣環境下加入40g的下述式(B-4)所表示的化合物及120g的四氫呋喃,於室溫下使其溶解。冷卻至0℃後,歷時0.5小時來滴加155g的烯丙基氯化鎂的四氫呋喃溶液(1M)。滴加結束後,加溫至60℃而進行3小時反應。反應結束後,將反應液添加於大量的水中後,添加120g的甲基異丁基酮而進行萃取。針對所獲得的有機層,實施兩次水洗後,投入至600g的己烷中而進行再沈澱。將所獲得的沈澱物濾出後,於60℃下減壓乾燥一晚,藉此而獲得所述化合物(A-4)。
[實施例1-5]
於實施例1-2中,使用下述式(B-5)所表示的化合物來代替化合物(B-2),除此以外與實施例1-2同樣地進行來合成所述化合物(A-5)。
[實施例1-6]
於實施例1-4中,使用下述式(B-6)所表示的化合物來代替化合物(B-4),除此以外與實施例1-4同樣地進行來合成所述化合物(A-6)。
[實施例1-7]
於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下加入40g的所述化合物(A-4)及200g的四氫呋喃,於室溫下使其溶解。冷卻至0℃後,添加15g的氫化鈉的油分散製劑(oil dispersion)(60質量%),反應1小時。添加46g的碘化甲烷後,於0℃下反應1小時。反應結束後,將反應液添加於大
量的水中後,添加120g的甲基異丁基酮而進行萃取。針對所獲得的有機層,實施兩次水洗後,投入至600g的己烷中而進行再沈澱。將所獲得的沈澱物濾出後,於60℃下減壓乾燥一晚,藉此而獲得所述化合物(A-7)(產率84%)。
[實施例1-8]
於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下添加190g的正丁基鋰的環己烷溶液(2.3M),冷卻至-78℃。於其中添加18g的四甲基乙二胺後,滴加36g的溴化炔丙基並攪拌20分鐘。對該溶液,滴加下述式(B-4)所表示的化合物40g的四氫呋喃40g溶液,歷時2小時升溫至室溫。反應結束後,將反應液添加於大量的水中後,添加120g的甲基異丁基酮而進行萃取。針對所獲得的有機層,實施兩次水洗後,投入至600g的己烷中而進行再沈澱。將所獲得的沈澱物濾出後,於60℃下減壓乾燥一晚,藉此而獲得所述化合物(A-8)(產率83%)。
[實施例1-9]
於具備溫度計、冷凝器及磁攪拌器的5,000mL的三口燒瓶中,於氮氣環境下,將0.2mol的1-甲醯基乙烯合萘與0.6mol的降冰片烯投入反應器中,溶於1-甲醯基乙烯合萘及降冰片烯的合計質量的3倍質量的1,2-二氯乙烷中後,攪拌30分鐘。緩緩投入0.01mol的偶氮雙異丁腈(azobisisobutyronitrile,AIBN),於70℃下反應12小時左右,獲得下述式(B-7)所表示的樹脂作為中間體。然後,緩緩添加0.07mol的烯丙基溴化鎂。以維持常溫的
狀態進行3小時反應後,添加300mL的蒸餾水來結束反應。於利用充分的水對有機層進行水洗後,僅將有機層另行分離,利用無水硫酸鎂將少量的水分去除。將固體過濾分離後,於減壓下自所獲得的溶液去除溶劑,獲得所述化合物(A-9)。化合物(A-9)的Mw為4,300。
[實施例1-10]
於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下,加入1-甲醯基乙烯合萘36g(200mmol)及1-甲醯基乙烯合萘的3倍質量的1,2-二氯乙烷,使其溶解後,攪拌30分鐘。緩緩投入20mmol的AIBN,於70℃下反應12小時左右。反應結束後,將反應液添加於大量的水中進行萃取。針對所獲得的有機層,實施兩次水洗後,投入至600g的己烷中而進行再沈澱。將所獲得的沈澱物濾出後,於60℃下減壓乾燥一晚,藉此而獲得下述式(B-8)所表示的樹脂。
其次,於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下加入15g的樹脂(B-8)及120g的四氫呋喃,於室溫下使其溶解。冷卻至0℃後,歷時0.5小時來滴加155g的烯丙基氯化鎂的四氫呋喃溶液(1M)。滴加結束後,加溫至60℃而進行3小時反應。反應結束後,將反應液添加於大量的水中後,添加120g的甲基異丁基酮而進行萃取。針對所獲得的有機層,實施兩次水洗後,投入至600g的己烷中而進行再沈澱。將所獲得的沈澱物濾出後,於60℃下減壓乾燥一晚,藉此而獲得所述
化合物(A-10)。化合物(A-10)的Mw為1,500。
[合成例1-1]
於具備溫度計、冷凝器及磁攪拌器的500mL的三口燒瓶中,於氮氣環境下,添加250g的間甲酚、125g的37質量%福馬林及2g的草酸酐,於100℃下反應3小時、180℃下反應1小時後,於減壓下將未反應單體去除,獲得下述式(a-1)所表示的樹脂。所獲得的樹脂(a-1)的Mw為11,000,Mw/Mn為8.4。
<抗蝕劑底層膜形成用組成物的製備>
以下示出抗蝕劑底層膜形成用組成物的製備中使用的[B]溶劑、[C]酸產生劑及[D]交聯劑。
[[B]溶劑]
B-1:丙二醇單甲醚乙酸酯
[[C]酸產生劑]
C-1:雙(4-第三丁基苯基)錪九氟-正丁磺酸鹽(下述式(C-1)所表示的化合物)
[[D]交聯劑]
D-1:1,3,4,6-四(甲氧基甲基)甘脲(下述式(D-1)所表示的化合物)
[實施例2-1]
將10質量份的作為[A]化合物的(A-1)及0.5質量份的作為[C]酸產生劑的(C-1)溶解於90質量份的作為[B]溶劑的(B-1)中。利用孔徑為0.1μm的薄膜過濾器對所獲得的溶液進行過濾,製備抗蝕劑底層膜形成用組成物(J-1)。
[實施例2-2~實施例2-12及比較例2-1]
除了使用下述表1所示的種類及含量的各成分以外,與實施例2-1同樣地進行操作,製備抗蝕劑底層膜形成用組成物(J-2)~抗蝕劑底層膜形成用組成物(J-13)。表1中的「-」表示未使用相當的成分。
<抗蝕劑底層膜的形成>
[實施例3-1~實施例3-12及比較例3-1]
藉由旋轉塗佈法將所述製備的抗蝕劑底層膜形成用組成物塗佈敷矽晶圓基板上。其次,於大氣環境下,以下述表2所示的加熱溫度(℃)及加熱時間(sec)進行加熱(煅燒),而形成平均厚度200nm的抗蝕劑底層膜,從而獲得於基板上形成有抗蝕劑底層膜的帶有抗蝕劑底層膜的基板。表2中的「-」表示比較例3-1為耐蝕刻性的評價的基準。
<評價>
使用所述獲得的抗蝕劑底層膜形成用組成物及所述獲得的帶有抗蝕劑底層膜的基板,利用下述方法對下述項目進行評價。將評價結果示於下述表2中。
[塗敷性]
對於於所述基板上形成有抗蝕劑底層膜的帶有抗蝕劑底層膜的基板,目視觀察自中心沿圓周方向的條狀缺陷(條紋)的有無。關於塗敷性,於不存在條狀缺陷(條紋)的情況下評價為「A」(良好),於存在缺陷的情況下評價為「B」(不良)。
[耐蝕刻性]
對於所述獲得的帶有抗蝕劑底層膜的基板中的抗蝕劑底層膜,使用蝕刻裝置(東京電子(Tokyo Electron)公司的「塔卡翠絲(TACTRAS)」),於CF4/Ar=110/440sccm、PRESS.=30MT、HF RF(電漿生成用高頻電力)=500W、LF RF(偏壓用高頻電力)=3000W、DCS=-150V、RDC(氣體感測器流量比)=50%、30sec的條件下進行處理,根據處理前後的抗蝕劑底層膜的平均厚度來
算出蝕刻速度(nm/min),算出相對於比較例3-1的比率,並設為耐蝕刻性的標準。關於耐蝕刻性,於所述比率為0.95以上、小於0.98的情況下評價為「A」(極其良好),於0.98以上、小於1.00的情況下評價為「B」(良好),於1.00以上的情況下評價為「C」(不良)。
[平坦性]
使用旋轉塗佈機(東京電子(Tokyo Electron)公司的「克林特拉庫(CLEAN TRACK)ACT12」),藉由旋轉塗佈法將所述製備的抗蝕劑底層膜形成用組成物塗敷於如圖1所示形成有深度100nm、寬度10μm的溝槽圖案的矽基板1上。旋轉塗佈的旋轉速度設為與在所述「抗蝕劑底層膜的形成」中,形成平均厚度200nm的抗蝕劑底層膜的情況相同。繼而,於大氣環境下,於250℃下煅燒(烘烤)60秒鐘,形成非溝槽圖案的部分中的平均厚度為200nm的膜2,從而獲得所述矽基板由膜所被覆的帶有膜的矽基板。
利用掃描型電子顯微鏡(日立高新技術(Hitachi High-technologies)公司的「S-4800」)來觀察所述帶有膜的矽基板的剖面形狀,並將該抗蝕劑底層膜的所述溝槽圖案的中央部分b的高度與距所述溝槽圖案的端部5μm的位置的非溝槽圖案部分a的高度之差(△FT)設為平坦性的指標。關於平坦性,於該△FT小於40nm的情況下評價為「A」(極其良好),於40nm以上、小於60nm的情況下評價為「B」(良好),於60nm以上的情況下評價為「C」(不良)。再者,圖1所示的高度的差較實際而言誇張地
記載。
[耐熱性]
藉由旋轉塗佈法將所述製備的抗蝕劑底層膜形成用組成物塗敷於直徑8英吋的矽晶圓上,於大氣環境下,於250℃下煅燒(烘烤)60秒鐘而形成抗蝕劑底層膜,從而獲得帶有抗蝕劑底層膜的基板。其次,削取該帶有抗蝕劑底層膜的基板的抗蝕劑底層膜,藉此回收粉體,將抗蝕劑底層膜的粉體放入至利用熱重差熱分析(thermogravimetry-differential thermal analysis,TG-DTA)裝置(耐馳(NETZSCH)公司的「TG-DTA2000SR」)的測定中所使用的容器中,測定加熱前的質量。繼而,使用所述TG-DTA裝置,於氮氣環境下,以10℃/min的升溫速度加熱至400℃為止,測定400℃下的粉體的質量。然後,藉由下述式來測定質量減少率(%),並將該質量減少率設為耐熱性的標準。
ML={(m1-m2)/m1}×100
此處,所述式中,ML為質量減少率(%),m1為加熱前的質量(mg),m2為400℃下的質量(mg)。
成為試樣的粉體的質量減少率越小,則抗蝕劑底層膜的加熱時產生的升華物或抗蝕劑底層膜的分解物越少,耐熱性越良好。即,質量減少率越小,則表示越高的耐熱性。耐熱性於質量減少率小於5%的情況下評價為「A」(極其良好),於5%以上、小於
10%的情況下評價為「B」(良好),於10%以上的情況下評價為「C」(不良)。
如表2的結果可知,實施例的抗蝕劑底層膜形成用組成物可形成發揮優異的塗敷性並且具有耐蝕刻性、平坦性及耐熱性的抗蝕劑底層膜。
[產業上之可利用性]
本發明的抗蝕劑底層膜形成用組成物可形成發揮優異的塗敷性並且耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜。本發明的抗蝕劑底層膜的耐蝕刻性、平坦性及耐熱性優異。根據本發明的抗蝕劑底層膜的形成方法,可形成發揮優異的塗敷性並且耐蝕刻性、平坦性及耐熱性優異的抗蝕劑底層膜。根據本發明的經圖案化基板的製造方法,可藉由使用所述形成的優異的抗蝕
劑底層膜而獲得具有良好的圖案形狀的基板。本發明的化合物可較佳地用作該抗蝕劑底層膜形成用組成物的成分。因此,該些可較佳地用於今後預計進一步進行微細化的半導體元件的製造等。
Claims (10)
- 一種抗蝕劑底層膜形成用組成物,其含有:具有下述式(1)所表示的基的化合物;以及溶劑,所述化合物的氧含量為3質量%~15質量%,
- 如申請專利範圍第1項所述的抗蝕劑底層膜形成用組 成物,其中所述化合物的氧含量為4質量%以上。
- 如申請專利範圍第1項或第2項所述的抗蝕劑底層膜形成用組成物,其中所述化合物具有芳香環。
- 如申請專利範圍第1項或第2項所述的抗蝕劑底層膜形成用組成物,其更含有酸產生劑。
- 如申請專利範圍第1項或第2項所述的抗蝕劑底層膜形成用組成物,其中所述化合物的含量為1質量%以上、50質量%以下。
- 一種抗蝕劑底層膜,其是由如申請專利範圍第1項至第6項中任一項所述的抗蝕劑底層膜形成用組成物所形成。
- 一種抗蝕劑底層膜的形成方法,其包括:將如申請專利範圍第1項至第6項中任一項所述的抗蝕劑底層膜形成用組成物塗敷於基板的其中一面側的步驟;以及對藉由所述塗敷步驟而獲得的塗敷膜進行加熱的步驟。
- 一種經圖案化基板的製造方法,其包括:於藉由如申請專利範圍第8項所述的抗蝕劑底層膜的形成方法而獲得的抗蝕劑底層膜的與所述基板相反的面側形成抗蝕劑圖案的步驟;以及進行以所述抗蝕劑圖案為遮罩的蝕刻的步驟。
- 一種化合物,其具有下述式(1)所表示的基,
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WO2014002810A1 (ja) * | 2012-06-29 | 2014-01-03 | 株式会社ダイセル | 高分子化合物、フォトレジスト用樹脂組成物、及び半導体の製造方法 |
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WO2018074534A1 (ja) | 2018-04-26 |
JP7029070B2 (ja) | 2022-03-03 |
JPWO2018074534A1 (ja) | 2019-08-29 |
KR102456451B1 (ko) | 2022-10-19 |
US11126084B2 (en) | 2021-09-21 |
US20190243247A1 (en) | 2019-08-08 |
TW201818151A (zh) | 2018-05-16 |
KR20190071701A (ko) | 2019-06-24 |
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