TW201918501A - 與光阻劑一起使用之下層塗料組合物 - Google Patents
與光阻劑一起使用之下層塗料組合物 Download PDFInfo
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- TW201918501A TW201918501A TW107135619A TW107135619A TW201918501A TW 201918501 A TW201918501 A TW 201918501A TW 107135619 A TW107135619 A TW 107135619A TW 107135619 A TW107135619 A TW 107135619A TW 201918501 A TW201918501 A TW 201918501A
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- hydrogen
- photoresist
- coating composition
- resin
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Classifications
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- G—PHYSICS
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Abstract
提供包括可顯示出標準電漿蝕刻劑增強之蝕刻速率之抗反射組合物的新組合物及方法。相對於現有組合物,本發明較佳之抗反射塗料組合物具有降低之碳含量。
Description
本發明係關於包括可顯示出標準電漿蝕刻劑增強之蝕刻速率之抗反射組合物的新組合物及方法。相對於現有組合物,本發明較佳之抗反射塗料組合物具有降低之碳含量。
光阻劑係用於將圖像轉移至基板上之感光膜。其形成負像或正像。在將光阻劑塗佈在基板上之後,藉由圖案化之光罩使塗層曝光於活化能來源,諸如紫外光,以在光阻劑塗層中形成潛像。光罩具有對活化輻射不透明及透明之區域,該等區域界定需要轉移至下層基板之圖像。藉由使抗蝕劑塗層中之潛像圖案顯影來提供浮雕圖像。
已知之光阻劑可提供解析度及尺寸足夠用於許多現有之商業應用之特徵。然而,對於許多其他應用而言,需要可提供亞微米級尺寸之高解析度圖像之新型光阻劑及相關材料以及製程。
用於曝光光阻劑之活化輻射之反射通常會對光阻劑層中圖案化之圖像之解析度造成限制。輻射自基板/光阻劑界面之反射可使光阻劑中之輻射強度產生空間變化,導致顯影時不均一之光阻劑線寬。輻射亦可自基板/光阻劑界面散射至光阻劑之非預期暴露區中,此又導致線寬變化。散射及反射之量通常在不同區域之間變化,此導致進一步之線寬不均一性。基板形貌之變化亦可引起解析度受限問題。
用於減少反射輻射問題之一種方法為使用***在基板表面與光阻劑塗層之間的輻射吸收層。此類層亦稱為抗反射層或抗反射組合物。參見US 9541834;US20150212414;US6767689B2;US6887648B2;及US8623589。亦參見美國專利8501383;8507192;及7183037。
雖然已發現現有之下層抗反射塗料組合物可能對許多抗反射應用而言是有效的,但彼等現有組合物亦可能造成一些潛在之效能限制。
具體而言,下層抗反射塗料組合物之蝕刻速率可能有問題。在下層抗反射塗料組合物層進行電漿蝕刻從而裸露基板(例如微電子晶片)表面期間,電漿蝕刻亦將移除上覆之顯影之光阻劑遮罩。在ARC完成後,必須保留抗蝕劑遮罩之有效厚度,以在裸露之基板表面加工期間起作用。然而,隨著移除ARC層所需之時間增加,光阻劑遮罩之劣化程度亦在增加。此為極不期望發生的。
應儘可能地最小化光阻劑之劣化,以塗覆薄光阻劑層。通常需要較薄之抗蝕劑層以提供圖案化圖像之最大解析度。若在下層抗反射塗料組合物蝕刻期間不希望之膜厚度損失(UFTL)顯著,則必須塗覆較厚之抗蝕劑層,以便在蝕刻過程結束時保留有效厚度之抗蝕劑遮罩。
因此將期望具有與外塗之光阻劑一起使用的新抗反射塗料組合物。特別期望具有藉由更快之蝕刻速率使光阻劑降解最小化之新抗反射塗料組合物。
現在發現新方法、塗佈之基板及特別適合用作193 nm有機底部抗反射塗料(BARC)之抗反射塗料組合物。將光阻劑塗覆在本發明抗反射塗料組合物之塗層上。
特別較佳之下層塗料組合物能夠顯示出電漿蝕刻劑如F2
/O2
電漿蝕刻劑增強之蝕刻速率。
在較佳態樣中,提供包含樹脂之下層塗料組合物,該樹脂包含含有下式(I)之結構之重複單元:其中R1
、R2
及R3
各自獨立地為氫或非氫取代基,其中R1
、R2
及R3
中之至少一個為-(CXY)(C=O)O-R,其中R為鍵聯至另一聚合物單元之鍵,且X及Y各自獨立地為氫或非氫取代基,例如鹵素或視情況經取代之烷基或視情況經取代之烷氧基;以及b)在塗料組合物層上塗覆一層光阻劑組合物。通常較佳地,X及Y中之一個或兩個為氫,亦即其中R1
、R2
及R3
中之至少一個為-CH2
(C=O)O-R。
在一個較佳態樣中,在式(I)中,R1
、R2
及R3
中之每一個均不為氫。在一個特別較佳之態樣中,R1
、R2
及R3
中之至少兩個為-(CXY)(C=O)O-R,其中R為鍵聯至另一聚合物單元之鍵,且X及Y各自獨立地為氫或非氫取代基,例如鹵素或視情況經取代之烷基或視情況經取代之烷氧基。較佳地,R1
、R2
及R3
中之至少一個:1)不為-(CXY)(C=O)O-R;且2)包含一個或多個氧原子。
在較佳態樣中,較佳樹脂可包含可由下式(II)之單體之反應得到的聚合基團:其中在式(II)中,P為氫或非氫取代基且可適當地為例如視情況經取代之烷氧基、視情況經取代之烷基或視情況經取代之羧基(例如-(C=O)OH)。
樹脂可進一步包括共價交聯劑單元,亦即諸如在塗覆之塗層進行熱能加熱(例如150℃,60秒)時反應之樹脂單元,以形成樹脂之間的共價鍵或以其他方式硬化所塗覆之組合物層。
樹脂可適當地具有7或更大之Ohnishi參數值,例如7.2、7.3、7.4、7.5、7.6、7.7、7.8、7.9、8.0或8.45或更大。如本文所提及,Ohnishi參數值計算為樹脂之原子總數(不包括氫)除以樹脂之碳原子總數減去樹脂之氧及氮原子總數的值。
在某些態樣中,下層塗料組合物可適當地包含不同於樹脂之交聯劑組分。
較佳地,可用活化輻射使外塗之光阻劑組合物成像,且使成像之光阻劑組合物層顯影以提供光阻劑浮雕圖像。如所討論,塗料組合物層可在塗覆光阻劑組合物層之前適當地進行熱處理。
本文進一步提供一種塗佈之基板,其包含:基板,上面具有:a)塗料組合物,該塗料組合物包含:1)包含重複單元之樹脂,該重複單元包含下式(I)之結構:其中R1
、R2
及R3
各自獨立地為氫或非氫取代基,其中R1
、R2
及R3
中之至少一個為-(CXY)(C=O)O-R,其中R為鍵聯至另一聚合物單元之鍵,且X及Y各自獨立地為氫或非氫取代基,例如鹵素或視情況經取代之烷基或視情況經取代之烷氧基;及b)塗料組合物層上之光阻劑組合物層。
本文亦提供用於形成光阻劑浮雕圖像之方法,該方法包含:a)在諸如半導體基板之基板上塗覆下層塗料組合物,及b)在上面塗覆光阻劑組合物層。
本發明之其他態樣論述於下文中。
在較佳態樣中,本文提供形成光阻劑浮雕圖像之方法。在一個態樣中,該方法可包括在基板上塗覆一層塗料組合物,且在塗料組合物層上塗覆一層光阻劑組合物。在另一個較佳態樣中,本文提供塗佈之基板,其包括基板、塗料組合物及塗料組合物層上之光阻劑組合物層。在進一步較佳態樣中,本文提供抗反射塗料組合物,其包括與外塗光阻劑組合物一起使用之樹脂。塗料組合物層
在一個較佳態樣中,塗料組合物或塗料組合物層可形成193 nm有機底部抗反射塗層(BARC),已知其為用於在光刻技術中控制反射率及增強光阻劑膜與基板之間的界面黏合之重要底層之一。最近,隨著用於微尺度圖案化之光阻劑(PR)之臨界尺寸減小,PR厚度減小以改善由較差之PR縱橫比所造成之物理圖案坍塌,因此,作為硬遮罩之有機BARC需要更快之蝕刻速率(E/R)效能以藉由減小PR厚度來改善蝕刻選擇性,且最小化緩慢E/R所引起之蝕刻偏差。
在一個態樣中,塗料組合物可包括包含重複單元之樹脂,該重複單元包含下式(I)之結構:其中R1
、R2
及R3
各自獨立地為氫或非氫取代基,其中R1
、R2
及R3
中之至少一個為-CH2
C(=O)O-R,其中R是鍵聯到另一樹脂單元之鍵;以及在塗料組合物層上塗覆一層光阻劑組合物。
在某些較佳態樣中,R1
、R2
及R3
中之每一個均不為氫。在一個較佳態樣中,R1
、R2
及R3
中之至少兩個為-CH2
C(=O)O-R,其中R為鍵聯至另一聚合物單元之鍵。在一個較佳態樣中,R1
、R2
及R3
中之至少一個:1)不為-CH2
C(=O)O-R;且2)包含一個或多個氧原子。
較佳地,聚合物可在193 nm浸沒式光刻中提供降低之反射率。
如上所述,較佳之樹脂可包含可由下式(II)之單體之應得到的聚合基團:其中在式(II)中,P為氫或非氫取代基,且可適當地為例如視情況經取代之烷氧基、視情況經取代之烷基或視情況經取代之羧基(例如-(C=O)OH)。
在一個示例性實施例中,下層塗料組合物之較佳樹脂可包含如下式(III)之括號內所示之結構。其中式(III)之R4
為可特別在熱處理(諸如50℃,60秒)時交聯或形成樹脂之間的共價鍵之基團;且R5
適當地為氫或非氫取代基,諸如視情況經取代之烷基、視情況經取代之烷氧基或視情況經取代之碳環烷基,其中一個、兩個或三個羥基為此類烷基、烷氧基或碳環芳基之較佳取代基。較佳之R4
基團包括含氮部分,諸如甘脲。
在以上式(I)、(II)及(III)中,合適之非氫取代基可為例如視情況經取代之C1-20烷基、視情況經取代之C1-20烷氧基,如視情況經取代之烷基(例如視情況經取代之C1-10烷基);視情況經取代之較佳地具有2至約20個碳原子之烯基或炔基,如烯丙基;視情況經取代之較佳地具有1至約20個碳原子之酮;視情況經取代之較佳地具有1至約20個碳原子之烷基硫基;視情況經取代之較佳地具有1至約20個碳原子之烷基亞磺醯基;視情況經取代之較佳地具有1至約20個碳原子之烷基磺醯基;視情況經取代之較佳地具有1至約20個碳原子之羧基(其包括諸COOR′之基團,其中R′為H或C1-8烷基,包括與光酸基本上不反應之酯)及其類似基團。
如本文,包括關於上述式(I)、(II)及(III)亦討論,各種取代基可適當地視情況經取代。「取代之」取代基可在一個或多個可供使用之位置、通常1、2或3個位置處經一個或多個合適之基團取代,該等合適之基團諸如鹵素(確切而言F、Cl或Br);氰基;硝基;C1-8
烷基;C1-8
烷氧基;C1-8
烷基硫基;C1-8
烷基磺醯基;C2-8
烯基;C2-8
炔基;羥基;硝基;烷醯基,例如C1-6
烷醯基,例如醯基;鹵烷基,確切而言C1-8
鹵烷基,例如CF3
;-CONHR、-CONRR’,其中R及R’為視情況經取代之C1-8
烷基;-COOH、COC、>C=O;及其類似基團。
在較佳之實施例中,本發明之下層塗料組合物之樹脂可包括一個或多個重複單元,該一個或多個重複單元包括在下列式(A)至(R)中之任一個之括號內描繪的結構:
其中彼等上述結構(A)至(R)中之「X-連接子」表示在熱處理過程中(例如170℃,60秒)可與其他樹脂單元反應之部分,諸如甘脲及其類似物。
在特定實施例中,本發明之下層塗料組合物之樹脂可包括一個或多個重複單元,該一個或多個重複單元包括在下列式(PA)至(PR)中之任一個之括號內描繪的結構:
在較佳實施例中,包括如本文所述之重複單元之樹脂可為包含樹脂之下層塗料組合物提供增加之蝕刻速率(E/R)。
本發明之下層塗料組合物的尤其較佳之樹脂可包含聚酯鍵。聚酯樹脂容易藉由一種或多種多元醇試劑與一種或多種含羧基(如羧酸、酯、酐等)化合物進行反應來製備。合適之多元醇試劑包括二醇、甘油及三醇,諸如二醇,諸如二醇為乙二醇、1,2-丙二醇、1,3-丙二醇、丁二醇、戊二醇、環丁二醇、環戊二醇、環己二醇、二羥甲基環己烷;及三醇,諸如甘油、三羥甲基乙烷、三羥甲基丙烷及其類似物。
如所討論,本發明之下層塗料組合物之較佳樹脂可包含氰尿酸酯(包括異氰尿酸酯)單元。包含聚酯鍵及氰尿酸酯單元之樹脂特別較佳。
較佳地,本發明之下層塗料組合物之樹脂將具有約1,000至約10,000,000道爾頓,更通常約2,000至約10,000道爾頓之重均分子量(Mw),及約500至約1,000,000道爾頓之數均分子量(Mn)。本發明組合物之樹脂之分子量(Mw或Mn)宜藉由凝膠滲透層析法測定。
在許多較佳實施例中,樹脂組分將為下層塗料組合物之主要固體組分。舉例而言,一或樹脂宜按塗料組合物之總固體含量計之50至99.9重量%,更通常按塗料組合物之總固體含量計之80或85至95、98或99+(或甚至100)重量%存在。如本文中所提及,塗料組合物之固體係指除了溶劑載劑以外之塗料組合物之所有物質。
容易製備用於本發明下層抗反射組合物中之合適及較佳之樹脂。參見例如以下實例1,其詳述異氰尿酸酯試劑反應提供聚酯氰尿酸酯樹脂。
如上所論述,在某些實施例中,本發明之塗料組合物除樹脂之外或作為樹脂之組分可包含交聯劑。舉例而言,塗料組合物可包括基於胺之交聯劑,諸如三聚氰胺物質,其包括三聚氰胺樹脂,諸如由氰特工業(Cytec Industries)製造且以商品名Cymel 300、301、303、350、370、380、1116及1130銷售之樹脂;甘脲,其包括購自氰特工業之彼等甘脲;及苯并二胺基三嗪(benzoquanamine)及基於脲之物質,其包括樹脂,諸如以名稱Cymel 1123及1125購自氰特工業之苯并二胺基三嗪樹脂及以名稱Powderlink 1174及1196購自氰特工業之脲樹脂。除可商購以外,此類基於胺之樹脂可例如藉由丙烯醯胺或甲基丙烯醯胺共聚物與甲醛在含醇溶液中反應,或者藉由N-烷氧基甲基丙烯醯胺或甲基丙烯醯胺與其他合適單體共聚來製備。
尤其用於反射控制應用之本發明之塗料組合物亦可含有吸收用於曝光外塗之光阻劑層之輻射的額外染料化合物。其他視情況選用之添加劑包括表面流平劑,例如可憑商品名Silwet 7604購得之流平劑,或購自3M公司之界面活性劑FC 171或FC 431。
本發明之下層塗料組合物亦可含有其他物質,諸如光酸產生劑,其包括如所論述之與外塗之光阻劑組合物一起使用的光酸產生劑。關於光酸產生劑在抗反射組合物中之此類用途之論述,參見美國專利6261743。
為製造液體下層塗料組合物,將塗料組合物之組分溶解於合適溶劑中,諸如一種或多種氧基異丁酸酯,尤其為甲基-2-羥基異丁酸酯,乳酸乙酯或諸如2-甲氧基***(二乙二醇二甲醚(diglyme))、乙二醇單甲醚及丙二醇單甲醚之二醇醚中之一種或多種;具有醚及羥基部分兩者之溶劑,如甲氧基丁醇、乙氧基丁醇、甲氧基丙醇及乙氧基丙醇;2-羥基異丁酸甲酯;酯,如溶纖劑乙酸甲酯、溶纖劑乙酸乙酯、丙二醇單甲醚乙酸酯、二丙二醇單甲醚乙酸酯及其他溶劑,如二元酯、碳酸伸丙酯及γ-丁內酯。溶劑中之乾組分之濃度將取決於若干因素,諸如塗覆方法。一般而言,下層塗料組合物之固體含量在塗料組合物之總重量之約0.5至20重量%範圍內變化,較佳地,固體含量在塗料組合物之約0.5至10重量%範圍內變化。光阻劑
與下層塗料組合物一起使用之光阻劑通常包含聚合物及一種或多種酸產生劑。一般較佳為正型抗蝕劑且抗蝕劑聚合物具有賦予抗蝕劑組合物鹼水溶性之官能基。舉例而言,較佳為包含極性官能基,諸如羥基或羧酸酯基,或在光刻加工後可釋放此類極性部分之酸不穩定基團的聚合物。較佳地,聚合物以足以使得抗蝕劑可用鹼性水溶液顯影之量用於抗蝕劑組合物中。
酸產生劑亦適宜與包含含有諸如包括酚之視情況經取代之苯基、視情況經取代之萘基及視情況經取代之蒽的芳族基之重複單元之聚合物一起使用。含有視情況經取代之苯基(包括酚)之聚合物尤其適用於多種抗蝕劑系統,包括用EUV及電子束輻射成像之彼等抗蝕劑系統。對於正性抗蝕劑,聚合物亦較佳含有一個或多個包含酸不穩定基團之重複單元。舉例而言,在含有視情況經取代之苯基或其他芳族基之聚合物的情況下,聚合物可包含含有一個或多個酸不穩定部分之重複單元,諸如藉由使丙烯酸酯或甲基丙烯酸酯化合物之單體與酸不穩定酯(例如丙烯酸第三丁酯或甲基丙烯酸第三丁酯)聚合而形成之聚合物。此類單體可與一種或多種包含芳族基(諸如視情況存在之苯基)之其他單體(例如苯乙烯或乙烯基苯酚單體)共聚。
用於形成此類聚合物之較佳單體包括:具有下式(IV)之酸不穩定單體、含內酯單體(V)及下式(VI)之極性控制單體,或包含前述單體中之至少一種之組合:其中每個R1
獨立地為H、F、-CN、C1-6
烷基或C1-6
氟烷基。在式(IV)之可酸脫除保護之單體中,R2
獨立地為C1-20
烷基、C3-20
環烷基或C6-20
芳基,且每個R2
為分開的或至少一個R2
與相鄰之R2
鍵結形成環狀結構。在式(V)之含內酯單體中,L1
為單環、多環或稠合多環C4-20
含內酯基團。
通式(IV)之單元包括酸不穩定基團,其在暴露於活化輻射及熱處理時經歷光酸促進之脫保護反應。這允許改變基質聚合物之極性,導致聚合物及光阻劑組合物在有機顯影劑中之溶解度發生變化。用於形成式(IV)單元之合適單體包括例如以下:、、、、、、、、、、、, 或包含前述單體中之至少一種之組合,其中R1
為H、F、-CN、C1-6
烷基或C1-6
氟烷基。
通式(V)之單元包括有效控制基質聚合物及光阻劑組合物之溶解速率之內酯部分。用於形成通式(V)之單元之合適單體包括例如以下:、、、、、、、、、, 或包含前述單體中之至少一種之組合,其中R1
為H、F、-CN、C1-6
烷基或C1-6
氟烷基。
式(VI)單元提供極性基團,其增強樹脂及光阻劑組合物之抗蝕刻性,且提供控制樹脂及光阻劑組合物之溶解速率之另外手段。用於形成式(VI)單元之單體包括甲基丙烯酸3-羥基-1-金剛烷酯(HAMA),較佳丙烯酸3-羥基-1-金剛烷酯(HADA)。
樹脂可包括一種或多種不同於第一單元之另外之通式(IV)、(V)及/或(VI)之單元。當樹脂中存在另外之此類單元時,其較佳包括另外之含離去基團之式(IV)單元及/或含內酯之式(V)單元。
除了上述聚合單元之外,樹脂亦可包括一種或多種另外之不具有通式(IV)、(V)或(VI)之單元。例如,特別合適之含內酯基之單元具有以下通式(VII):其中:R1
為H、F、-CN、C1-6
烷基或C1-6
氟烷基、雜環烷基,R3
為(C1
-C3
)亞烷基,且L2
為內酯基。以下示例性單體適用於形成另外之通式(VII)之內酯單元:、、、、、、, 或包含前述單體中之至少一種之組合,其中R1
為H、F、-CN、C1-6
烷基或C1-6
氟烷基。
特別適用於本發明正性化學增幅型光阻劑中的具有酸不穩定之去封閉基團之聚合物已於歐洲專利申請案0829766A2(具有縮醛之聚合物及縮酮聚合物)及歐洲專利申請案EP0783136A2(包括1)苯乙烯;2)羥基苯乙烯;及3)酸不穩定基團,特別是丙烯酸烷酯酸不穩定基團之單元之三元共聚物及其他共聚物)中揭示。
用於本發明光阻劑中之聚合物之分子量及多分散性可適當地大幅變化。合適之聚合物包括Mw
為約1,000至約50,000,更通常約2,000至約30,000且分子量分佈為約3或更小,更通常分子量分佈為約2或更小之彼等聚合物。
較佳之本發明負性組合物包含在暴露於酸後將固化、交聯或硬化之物質與兩種或更多種如本文中所揭示之酸產生劑的混合物。較佳之負性組合物包含聚合物黏合劑(如酚系或非芳族聚合物)、交聯劑組分及本發明之光敏組分。此類組合物及其用途已揭示於Thackeray等人之歐洲專利申請案0164248及美國專利第5,128,232號中。用作聚合物黏合劑組分之較佳酚系聚合物包括酚醛清漆及聚(乙烯基苯酚),如上文所論述之彼等組分。較佳之交聯劑包括基於胺之物質,包括三聚氰胺、甘脲、基於苯并胍胺之物質及基於脲之物質。三聚氰胺-甲醛聚合物通常尤其合適。此類交聯劑可購得,例如三聚氰胺聚合物、甘脲聚合物、基於脲之聚合物及苯并胍胺聚合物,如由氰特以商品名Cymel 301、303、1170、1171、1172、1123及1125以及Beetle 60、65及80銷售之彼等交聯劑。
尤其較佳之本發明光阻劑可用於浸沒式光刻應用中。關於較佳之浸沒式光刻光阻劑及方法之論述,參見例如羅門哈斯電子材料公司(Rohm and Haas Electronic Materials)之U.S. 7968268。
本發明之光阻劑亦可包含單一酸產生劑或不同酸產生劑之混合物,通常2種或3種不同酸產生劑之混合物,更通常由總共2種不同酸產生劑組成之混合物。光阻劑組合物包含以在曝光於活化輻射後足以在組合物之塗層中產生潛像之量採用的酸產生劑。舉例而言,酸產生劑將適宜以按光阻劑組合物之總固體計,1至20重量%之量存在。
合適之酸產生劑為化學增幅型光阻劑領域中已知且包括例如:鎓鹽,例如三氟甲烷磺酸三苯基鋶、三氟甲烷磺酸(對第三丁氧基苯基)二苯基鋶、三氟甲烷磺酸三(對第三丁氧基苯基)鋶、對甲苯磺酸三苯基鋶;硝基苯甲基衍生物,例如2-硝基苯甲基-對甲苯磺酸鹽、2,6-二硝基苯甲基-對甲苯磺酸鹽及2,4-二硝基苯甲基-對甲苯磺酸鹽;磺酸酯,例如1,2,3-三(甲烷磺醯基氧基)苯、1,2,3-三(三氟甲烷磺醯基氧基)苯及1,2,3-三(對甲苯磺醯基氧基)苯;重氮甲烷衍生物,例如雙(苯磺醯基)重氮甲烷、雙(對甲苯磺醯基)重氮甲烷;乙二肟衍生物,例如雙-O-(對甲苯磺醯基)-α-二甲基乙二肟及雙-O-(正丁烷磺醯基)-α-二甲基乙二肟;N-羥基醯亞胺化合物之磺酸酯衍生物,例如N-羥基丁二醯亞胺甲磺酸酯、N-羥基丁二醯亞胺三氟甲磺酸酯;以及含鹵素之三嗪化合物,例如2-(4-甲氧基苯基)-4,6-雙(三氯甲基)-1,3,5-三嗪及2-(4-甲氧基萘基)-4,6-雙(三氯甲基)-1,3,5-三嗪。
如本文中所提及,酸產生劑可在曝光於活化輻射,諸如EUV輻射、電子束輻射、193 nm波長輻射或其他輻射源後產生酸。如本文中所提及之酸產生劑化合物亦可稱為光酸產生劑化合物。
本發明之光阻劑亦可含有其他物質。舉例而言,其他視情況選用之添加劑包括光化及造影染料、抗條紋劑、增塑劑、速度促進劑及敏化劑。此類視情況選用之添加劑通常將以較小濃度存在於光阻劑組合物中。
或者或另外,其他添加劑可包括淬滅劑,其為光無法破壞之鹼,如基於氫氧化物、羧酸鹽、胺、亞胺及醯胺之彼等鹼。較佳地,此類淬滅劑包括C1-30
有機胺、亞胺或醯胺,或可為強鹼(例如氫氧化物或醇鹽)或弱鹼(例如羧酸鹽)之C1-30
四級銨鹽。示例性淬滅劑包括胺,如三丙胺、十二烷胺、三(2-羥丙基)胺、四(2-羥丙基)乙二胺;芳基胺,如二苯胺、三苯胺、胺基苯酚及2-(4-胺基苯基)-2-(4-羥基苯基)丙烷;受阻胺,如二氮雜雙環十一烯(DBU)或二氮雜二環壬烯(DBN);或離子淬滅劑,包括四級烷基銨鹽,如氫氧化四丁基銨(TBAH)或乳酸四丁基銨。
界面活性劑包括氟化及非氟化之界面活性劑,且較佳為非離子型。示例性氟化非離子型界面活性劑包括全氟C4
界面活性劑,諸如可自3M公司購得之FC-4430及FC-4432界面活性劑;及氟二醇,如來自歐諾法(Omnova)之POLYFOX PF-636、PF-6320、PF-656及PF-6520含氟界面活性劑。
光阻劑進一步包括一般適用於溶解、施配及塗佈光阻劑中所用組分之溶劑。示例性溶劑包括苯甲醚;醇,包括乳酸乙酯、1-甲氧基-2-丙醇及1-乙氧基-2丙醇;酯,包括乙酸正丁酯、乙酸1-甲氧基-2-丙酯、甲氧基乙氧基丙酸酯、乙氧基乙氧基丙酸酯;酮,包括環己酮及2-庚酮;以及包含前述溶劑中之至少一種之組合。光刻加工
在使用中,本發明之塗料組合物藉由諸如旋塗之多種方法中之任一種以塗層形式塗覆至基板。塗料組合物一般以約0.02與0.5 mm之間的乾燥層厚度,較佳地約0.04與0.20 mm之間的乾燥層厚度塗覆於基板上。基板宜為任何用於涉及光阻劑之製程中的基板。舉例而言,基板可為矽、二氧化矽或鋁-氧化鋁微電子晶片。亦可採用砷化鎵、碳化矽、陶瓷、石英或銅基板。亦宜採用用於液晶顯示器或其他平板顯示器應用之基板,例如玻璃基板、氧化銦錫塗佈之基板及其類似物。亦可採用用於光學及光電裝置(例如波導)之基板。
較佳地,塗覆之塗層在光阻劑組合物塗覆於下層塗料組合物上之前固化。固化條件將隨著下層塗料組合物之組分而有所變化。確切而言,固化溫度將取決於塗料組合物中所用之特定酸或酸(熱)產生劑。典型固化條件為約60℃至225℃下持續約0.5至5分鐘。已發現,如本文中所揭示之較佳抗反射組合物之塗層可有效地經受在相對較低之溫度,例如55℃或60℃-75℃下硬化。固化條件較佳地使得塗料組合物塗層基本上不溶於所用之光阻劑溶劑以及顯影劑溶液。
在此類固化之後,將光阻劑塗覆於塗覆之塗料組合物之表面上。如同底部塗料組合物層之塗覆一般,外塗之光阻劑可藉由任何標準方法,諸如藉由旋塗、浸塗、彎月面塗佈或滾塗來塗覆。在塗覆後,光阻劑塗層通常藉由加熱來乾燥以移除溶劑,較佳地直到抗蝕劑層無黏性為止。最優地,應基本上不出現底部組合物層與外塗之光阻劑層的互混。
接著抗蝕劑層以常規方式藉由遮罩用活化輻射,諸如248 nm、193 nm或EUV輻射成像。曝光能量足以有效地活化抗蝕劑系統之光敏組分以在抗蝕劑塗層中產生圖案化圖像。通常,曝光能量之範圍介於約3至300 mJ/cm2
且部分取決於採用之曝光工具及特定之抗蝕劑及抗蝕劑加工。曝光之抗蝕劑層可在必要時經受曝光後烘烤以在塗層之曝光區與未曝光區之間產生或增強溶解性差異。舉例而言,負型酸硬化光阻劑通常需要曝光後加熱以誘導酸促進之交聯反應,且許多化學增幅型正性抗蝕劑需要曝光後加熱以誘導酸促進之脫保護反應。通常,曝光後烘烤條件包括約50℃或更高之溫度,更確切而言,約50℃至約160℃範圍內之溫度。
光阻劑層亦可曝光於浸沒式光刻系統中,亦即其中曝光工具(尤其投影透鏡)與光阻劑塗佈之基板之間的空間經浸沒流體,如水或與一種或多種添加劑(如可提供增強之折射率之流體的硫酸銫)混合之水佔據。較佳地,浸沒流體(例如水)已加以處理以避免氣泡,例如水可進行脫氣以避免奈米氣泡。
本文中提及「浸沒曝光」或其他類似術語指示該曝光係在此類流體層(例如水或具有添加劑之水)***在曝光工具與塗佈之光阻劑組合物層之間的情況下進行。
接著將曝光之光阻劑層用能夠選擇性地移除膜之一部分以形成光阻劑圖案之合適顯影劑處理。在負型顯影(NTD)製程中,光阻劑層之未曝光區可藉由用合適之非極性溶劑處理而選擇性地移除。關於負型顯影之合適程序,參見U.S. 2011/0294069。用於負型顯影之典型非極性溶劑為有機顯影劑,諸如選自酮、酯、烴及其混合物之溶劑,例如丙酮、2-己酮、2-庚酮、乙酸甲酯、乙酸丁酯及四氫呋喃。用於NTD製程中之光阻劑材料較佳地形成可與有機溶劑顯影劑形成負像或與諸如氫氧化四烷基銨溶液之水性鹼顯影劑形成正像之光阻劑層。較佳地,NTD光阻劑係基於具有酸敏性(可脫除保護)基團之聚合物,該等基團在脫除保護時形成羧酸基及/或羥基。
或者,曝光之光阻劑層之顯影可藉由用能夠選擇性地移除膜之曝光部分(其中光阻劑是正型)或移除膜之未曝光部分(其中光阻劑在曝光區中可交聯,亦即為負型)之合適顯影劑處理曝光層來實現。較佳地,光阻劑為正型,其基於具有在脫除保護時形成羧酸基之酸敏性(可脫除保護)基團之聚合物,且顯影劑較佳為不含金屬離子之氫氧化四烷基銨溶液,如0.26 N氫氧化四甲基銨水溶液。圖案藉由顯影而形成。
接著顯影之基板可根據本領域中熟知之程序在缺乏光阻劑之彼等基板區域,例如缺乏光阻劑之化學蝕刻或鍍敷基板區域上選擇性地加工。合適之蝕刻劑包括氫氟酸蝕刻溶液及電漿氣體蝕刻,如氧電漿蝕刻。電漿氣體蝕刻移除底層塗層。
如所論述,在某些態樣中,可適當地採用濕法蝕刻製程。濕法蝕刻可適當地藉由用濕法蝕刻組合物暴露待蝕刻之表面(例如金屬氮化物,或塗佈有一個或多個有機層及/或無機層之金屬氮化物)一定時間及溫度以有效蝕刻表面(例如金屬氮化物表面及/或其上之塗層)來進行。示例性之濕法蝕刻組合物包括氫氧化銨及諸如過氧化氫之過氧化物的水性混合物,或諸如硫酸之酸及諸如過氧化氫之過氧化物的混合物。示例性組合物參見US 2006/0226122。下面之實例亦提供示例性濕法蝕刻製程條件。如本文所提及,「濕法蝕刻製程」意謂用流體組合物處理由鄰接之光阻劑限定之基板區域(在光阻劑圖像顯影之後),該流體組合物通常為酸性或鹼性,與過氧化物劑組合,但無論如何均與電漿乾法蝕刻不同。
以下非限制性實例係對本發明之說明。 實例1-4:聚合物合成 實例1:聚合物合成
將100 ml之3頸圓底燒瓶配備熱電偶、迪安-斯塔克裝置(Dean-stark)、冷凝器及加熱油浴。將三(2-羥乙基)異氰尿酸酯(17.83 g,68.2 mmol)、2,2',2''-(2,4,6-三側氧基-1,3,5-三嗪烷-1,3,5-三基)三乙酸三第三丁酯(32.17 g,68.2 mmol)、正丁醇(40.0 g,540.0 mmol)、對甲苯磺酸(0.39 g,2.0 mmol)及34 g苯甲醚稱入燒瓶中。將其加熱至設定溫度(105℃)且攪拌5小時,將其再加熱至設定溫度(150℃)且攪拌6.5小時。然後將溶液冷卻至室溫。將粗反應混合物用THF(70 g)稀釋以進行分離。用MTBE(700 g)沈澱反應混合物,然後過濾且在40℃下真空乾燥24小時。將100 ml之3頸圓底燒瓶配備熱電偶、冷凝器及加熱油浴。將預聚物(20 g)、對甲苯磺酸(0.15 g,0.79 mmol)、1,3,4,6-四(丁氧基甲基)四氫咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(11.4 g,23.4 mmol)及80 g 2-羥基異丁酸甲酯(HBM)稱入燒瓶中。將其加熱至設定溫度(50℃)且攪拌4小時。用三乙胺(TEA)(0.5 mL)淬滅溶液。然後將溶液冷卻至室溫。用異丙醇(IPA)(1000 g)沈澱反應混合物,然後過濾且在40℃下真空乾燥24小時。 實例2:聚合物合成
將100 ml之3頸圓底燒瓶配備熱電偶、迪安-斯塔克裝置、冷凝器及加熱油浴。將三(2-羥乙基)異氰尿酸酯(25.91 g,99.2 mmol)、2,2',2''-(2,4,6-三側氧基-1,3,5-三嗪烷-1,3,5-三基)三乙酸三第三丁酯(24.09 g,51.1 mmol)、正丁醇(40.0 g,540.0 mmol)、對甲苯磺酸(0.43 g,2.2 mmol)及34 g苯甲醚稱入燒瓶中。將其加熱至設定溫度(105℃)且攪拌5小時,將其再加熱至設定溫度(150℃)且攪拌10小時。然後將溶液冷卻至室溫。將粗物質用THF(70 g)稀釋以進行分離。用甲基第三丁基酯(MTBE)(700 g)沈澱反應混合物,然後過濾且在40℃下真空乾燥24小時。將100 ml之3頸圓底燒瓶配備熱電偶、冷凝器及加熱油浴。將預聚物(20 g)、對甲苯磺酸(0.15 g,0.79 mmol)、1,3,4,6-四(丁氧基甲基)四氫咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(11.4 g,23.4 mmol)及80 g HBM稱入燒瓶中。將其加熱至設定溫度(50℃)且攪拌4小時。用TEA(0.5 mL)淬滅溶液。然後將溶液冷卻至室溫。用IPA(1000 g)沈澱反應混合物,過濾,然後在40℃下真空乾燥24小時。 實例3:聚合物合成
將100 ml之3頸圓底燒瓶配備熱電偶、迪安-斯塔克裝置、冷凝器及加熱油浴。將三(2-羥乙基)異氰尿酸酯(14.76 g,56.5 mmol)、2,2',2''-(2,4,6-三側氧基-1,3,5-三嗪烷-1,3,5-三基)三乙酸三第三丁酯(26.64 g,56.5 mmol)、1,2-丙二醇(8.60 g,113.0 mmol)、對甲苯磺酸(0.43 g,2.2 mmol)及34 g苯甲醚稱入燒瓶中。將其加熱至設定溫度(150℃)且攪拌1小時。然後將溶液冷卻至室溫。將粗物質用THF(80 g)稀釋以進行分離。用MTBE(800 g)沈澱反應混合物,然後過濾且在40℃下真空乾燥24小時。將100 ml之3頸圓底燒瓶配備熱電偶、冷凝器及加熱油浴。將預聚物(20 g)、對甲苯磺酸(0.15 g,0.79 mmol)、1,3,4,6-四(丁氧基甲基)四氫咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(11.4 g,23.4 mmol)及80 g HBM稱入燒瓶中。將其加熱至設定溫度(50℃)且攪拌4小時。用TEA(0.5 mL)淬滅溶液。然後將溶液冷卻至室溫。用IPA(1000 g)沈澱反應混合物,然後過濾且在40℃下真空乾燥24小時。 實例4:聚合物合成
將100 ml之3頸圓底燒瓶配備熱電偶、迪安-斯塔克裝置、冷凝器及加熱油浴。將三(2-羥乙基)異氰尿酸酯(30.43 g,116.5 mmol)、三(2-羧基乙基)異氰尿酸酯(20.11 g,58.2 mmol)、正丁醇(20.0 g,270.0 mmol)、對甲苯磺酸(0.54 g,2.8 mmol)及34 g苯甲醚稱入燒瓶中。將其加熱至設定溫度(150℃)且攪拌3小時。然後將溶液冷卻至室溫。用HBM(160 g)稀釋粗物質。將100 ml之3頸圓底燒瓶配備熱電偶、冷凝器及加熱油浴。將預聚物溶液(40 g)、對甲苯磺酸(0.08 g,0.42 mmol)及1,3,4,6-四(丁氧基甲基)四氫咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(5.0 g,10.3 mmol)稱入燒瓶中。將其加熱至設定溫度(50℃)且攪拌4小時。用TEA(0.5 mL)淬滅溶液。然後將溶液冷卻至室溫。用IPA(300 g)及庚烷(200 g)沈澱反應混合物,然後過濾且在40℃下真空乾燥24小時。 實例5-8:塗料組合物之配製 實例5
將0.947 g上述實例1中製備之聚合物及0.013 g對甲苯磺酸2,4,6-三甲基吡啶鎓鹽溶於99.0 g 2-羥基異丁酸甲酯(HBM)溶劑中,得到塗料組合物。 實例6
將0.947 g實例2中製備之聚合物及0.013 g對甲苯磺酸2,4,6-三甲基吡啶鎓鹽溶於99.0 g HBM溶劑中,得到塗料組合物。 實例7
將0.947 g實例3中製備之聚合物及0.013 g對甲苯磺酸2,4,6-三甲基吡啶鎓鹽溶於99.0 g HBM溶劑中,得到塗料組合物。 實例8(比較實例)
將0.947 g實例4中製備之聚合物及0.013 g對甲苯磺酸2,4,6-三甲基吡啶鎓鹽溶於99.0 g HBM溶劑中,得到組合物。 實例9:抗反射組合物之評估條件
下表1係用於評估本發明抗反射組合物之示例性製程條件。 表1
實例10-11:光刻製程及效能評估 實例10:光刻測試條件
下表2列出光刻評估之示例性製程及照射條件。 表2
*抗蝕劑係193 nm化學增幅型正性配製物與甲基丙烯酸酯樹脂。 實例11:蝕刻速率及光刻效能
如上所揭示,將實例5-8之組合物旋塗至半導體晶片上。
實例5-7之組合物及聚合物顯示出更快之E/R效能,與Ohnishi參數值協調,且特別地,藉由n/k與實例8(比較實例)類似,實例7顯示出最快之E/R,及相當之EL/圖案坍塌寬容度(PCM)及DoF寬容度。下表3顯示CF4
/Ar氣體之蝕刻速率結果,且表4顯示上述實例5-8之組合物之光刻效能總結。 表3
表4
Claims (15)
- 一種形成光阻劑浮雕圖像之方法,該方法包含: a) 在基板上塗覆一層包含以下之塗料組合物: 包含重複單元之樹脂,該重複單元包含下式(I)之結構:其中R1 、R2 及R3 各自獨立地為氫或非氫取代基,其中R1 、R2 及R3 中之至少一個為-(CXY)(C=O)O-R,其中R為鍵聯至另一聚合物單元之鍵且X及Y各自獨立地為氫或非氫取代基;及 b) 在該塗料組合物層上塗覆一層光阻劑組合物。
- 根據申請專利範圍第1項所述之方法,其中R1 、R2 及R3 中之至少一個為-CH2 C(=O)O-R,其中R為鍵聯至另一聚合物單元之鍵。
- 根據申請專利範圍第1項或第2項所述之方法,其中R1 、R2 及R3 中之每一個均不為氫原子。
- 根據申請專利範圍第1項至第3項中任一項所述之方法,其中R1 、R2 及R3 中之至少兩個為-CH2 (C=O)O-R,其中R為鍵聯至另一聚合物單元之鍵。
- 根據申請專利範圍第1項至第4項中任一項所述之方法,其中R1 、R2 及R3 中之至少一個:1)不為-CH2 (C=O)O-R,且2)包含一個或多個氧原子。
- 根據申請專利範圍第1項至第5項中任一項所述之方法,該樹脂包含可由下式(II)之單體之反應獲得的聚合基團:其中在式(II)中,P為氫或非氫取代基。
- 根據申請專利範圍第1項至第6項中任一項所述之方法,其中該樹脂進一步包含交聯劑單元。
- 根據申請專利範圍第1項至第7項中任一項所述之方法,其中該樹脂包含括號內所示之以下結構之一個或多個: 其中在每個結構中,X-連接子為非氫取代基。
- 根據申請專利範圍第8項所述之方法,其中X-連接子為可交聯之部分。
- 根據申請專利範圍第1項至第9項中任一項所述之方法,其中該聚合物具有7或更大之Ohnishi 參數值。
- 根據申請專利範圍第1項至第10項中任一項所述之方法,其中該塗料組合物進一步包含不同於該樹脂之交聯劑組分。
- 根據申請專利範圍第1項至第11項所述之方法,其中該光阻劑組合物用活化輻射成像且使成像之光阻劑組合物層顯影,得到光阻劑浮雕圖像。
- 根據申請專利範圍第1項至第12項中任一項所述之方法,其中該塗料組合物層在塗覆該光阻劑組合物層之前進行熱處理。
- 一種塗佈之基板,其包含: 基板,上面具有: a)包含以下之塗料組合物: 1)包含重複單元之樹脂,該重複單元包含下式(I)之結構:其中R1 、R2 及R3 各自獨立地為氫或非氫取代基,其中R1 、R2 及R3 中之至少一個為-CXY(C=O)O-R,其中R為鍵聯至另一聚合物單元之鍵且X及Y各自獨立地為氫或非氫取代基;及 2)經取代之異氰尿酸酯化合物;及 b)該塗料組合物層上之一層光阻劑組合物。
- 一種與外塗之光阻劑組合物一起使用之抗反射塗料組合物,該抗反射塗料組合物包含: 1)包含重複單元之樹脂,該重複單元包含下式(I)之結構:(I) 其中R1 、R2 及R3 各自獨立地為氫或非氫取代基,其中R1 、R2 及R3 中之至少一個為-CXY(C=O)O-R,其中R為鍵聯至另一聚合物單元之鍵且X及Y各自獨立地為氫或非氫取代基。
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KR20220024079A (ko) * | 2019-06-17 | 2022-03-03 | 닛산 가가쿠 가부시키가이샤 | 디시아노스티릴기를 갖는 복소환 화합물을 포함하는 웨트에칭가능한 레지스트 하층막 형성 조성물 |
US11269252B2 (en) | 2019-07-22 | 2022-03-08 | Rohm And Haas Electronic Materials Llc | Method for forming pattern using antireflective coating composition including photoacid generator |
US20220397827A1 (en) * | 2021-05-28 | 2022-12-15 | Rohm And Haas Electronic Materials Korea Ltd. | Composition for photoresist underlayer |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3230220A (en) * | 1961-04-24 | 1966-01-18 | Gulf Oil Corp | Isocyanurate compounds and preparative processes |
US4053538A (en) * | 1976-04-09 | 1977-10-11 | Armstrong Cork Company | Block polymers from isocyanurate-based polyesters and conventional polyester segments |
DE3584316D1 (de) | 1984-06-01 | 1991-11-14 | Rohm & Haas | Lichtempfindliche beschichtungszusammensetzung, aus diesem hergestellte thermisch stabile beschichtungen und verfahren zur herstellung von thermisch stabilen polymerbildern. |
US5128232A (en) | 1989-05-22 | 1992-07-07 | Shiply Company Inc. | Photoresist composition with copolymer binder having a major proportion of phenolic units and a minor proportion of non-aromatic cyclic alcoholic units |
US5939236A (en) | 1997-02-07 | 1999-08-17 | Shipley Company, L.L.C. | Antireflective coating compositions comprising photoacid generators |
AU8500701A (en) | 2000-08-17 | 2002-02-25 | Shipley Co Llc | Etch resistant antireflective coating compositions |
TW576859B (en) | 2001-05-11 | 2004-02-21 | Shipley Co Llc | Antireflective coating compositions |
AU2003271123A1 (en) * | 2002-10-09 | 2004-05-04 | Nissan Chemical Industries, Ltd. | Composition for forming antireflection film for lithography |
CN100547487C (zh) | 2002-10-09 | 2009-10-07 | 日产化学工业株式会社 | 光刻用形成防反射膜的组合物 |
US20060226122A1 (en) | 2005-04-08 | 2006-10-12 | Wojtczak William A | Selective wet etching of metal nitrides |
EP1720072B1 (en) | 2005-05-01 | 2019-06-05 | Rohm and Haas Electronic Materials, L.L.C. | Compositons and processes for immersion lithography |
US7919222B2 (en) * | 2006-01-29 | 2011-04-05 | Rohm And Haas Electronics Materials Llc | Coating compositions for use with an overcoated photoresist |
US8501383B2 (en) | 2009-05-20 | 2013-08-06 | Rohm And Haas Electronic Materials Llc | Coating compositions for use with an overcoated photoresist |
US8486609B2 (en) * | 2009-12-23 | 2013-07-16 | Az Electronic Materials Usa Corp. | Antireflective coating composition and process thereof |
US8507192B2 (en) * | 2010-02-18 | 2013-08-13 | Az Electronic Materials Usa Corp. | Antireflective compositions and methods of using same |
IL213195A0 (en) | 2010-05-31 | 2011-07-31 | Rohm & Haas Elect Mat | Photoresist compositions and emthods of forming photolithographic patterns |
US8623589B2 (en) | 2011-06-06 | 2014-01-07 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions and processes thereof |
US9541834B2 (en) | 2012-11-30 | 2017-01-10 | Rohm And Haas Electronic Materials Llc | Ionic thermal acid generators for low temperature applications |
JP2018119996A (ja) * | 2015-05-28 | 2018-08-02 | 富士フイルム株式会社 | 基板処理方法、樹脂組成物及び電子デバイスの製造方法 |
TWI646397B (zh) * | 2015-10-31 | 2019-01-01 | 南韓商羅門哈斯電子材料韓國公司 | 與外塗佈光致抗蝕劑一起使用的塗料組合物 |
US11262656B2 (en) | 2016-03-31 | 2022-03-01 | Rohm And Haas Electronic Materials Korea Ltd. | Coating compositions for use with an overcoated photoresist |
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CN109725492B (zh) | 2022-09-02 |
TWI709587B (zh) | 2020-11-11 |
CN109725492A (zh) | 2019-05-07 |
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US20190129305A1 (en) | 2019-05-02 |
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