TWI745613B - 具有熱酸產生劑的抗反射組合物 - Google Patents

具有熱酸產生劑的抗反射組合物 Download PDF

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TWI745613B
TWI745613B TW107130174A TW107130174A TWI745613B TW I745613 B TWI745613 B TW I745613B TW 107130174 A TW107130174 A TW 107130174A TW 107130174 A TW107130174 A TW 107130174A TW I745613 B TWI745613 B TW I745613B
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composition
photoresist
coating
formula
layer
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TW201914992A (zh
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李晶真
林載峰
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南韓商羅門哈斯電子材料韓國公司
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
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    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract

提供新穎方法及基板，其包括含有一或多種熱酸產生劑的抗反射組合物。

Description

具有熱酸產生劑的抗反射組合物
本發明涉及新型方法及基板，其包括含有一或多種熱酸產生劑的抗反射組合物。
光致抗蝕劑為用於將圖像轉移至基板上的感光膜。其形成負像或正像。在將光致抗蝕劑塗佈在基板上之後，經由圖案化光罩使塗層曝光於活化能來源（諸如紫外光），以在光致抗蝕劑塗層中形成潛像。光罩具有對活化輻射不透明及透明的區域，其界定需要轉移至底層基板的圖像。藉由使抗蝕劑塗層中的潛像圖案顯影來提供浮雕圖像。
已知光致抗蝕劑可提供解析度及尺寸足以用於許多現有商業應用的特徵。然而，對於許多其他應用，需要可提供亞微米級尺寸的高解析度圖像的新型光致抗蝕劑及相關材料以及製程。
用於曝光光致抗蝕劑的活化輻射的反射通常對光致抗蝕劑層中圖案化的圖像的解析度造成限制。來自基板/光致抗蝕劑界面的輻射的反射可使光致抗蝕劑中的輻射強度產生空間變化，導致顯影時的非均一光致抗蝕劑線寬。輻射亦可自基板/光致抗蝕劑界面散射至光致抗蝕劑的非所意圖曝光的區域中，再次導致線寬變化。散射及反射的量通常在不同區域之間變化，導致進一步的線寬非均一性。基板形貌的變化亦會引起解析度受限問題。
用於減少反射輻射問題的一種方法為使用插在基板表面與光致抗蝕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。
將期望具有與外塗光致抗蝕劑組合物一起使用的新型抗反射塗料組合物。
現已發現新型方法，其包括使用包含樹脂組分及一或多種熱酸產生劑化合物的抗反射組合物。將光致抗蝕劑塗覆在本發明抗反射組合物的塗層上。
亦提供新型抗反射塗料組合物，其用於外塗光致抗蝕劑組合物層。
特別提供的底層抗反射組合物可表現出增強的塗層特性。較佳的抗反射組合物亦可在相對較低的溫度下硬化或交聯。例如，參見下面的比較結果。
已發現，使用相對親水的聚合物，諸如聚酯樹脂，或包含異氰尿酸酯單元的樹脂，或含有異氰尿酸酯取代的聚酯樹脂，可在外塗的光致抗蝕劑層的微影處理中減少缺陷。然而，亦發現，使用此類親水性聚合物會損害抗反射組合物在底層基板，諸如微電子晶圓上的塗層覆蓋，包括由於親水性聚合物的非所期望的聚集，因為抗反射組合物層經熱處理而在塗覆外塗光致抗蝕劑層之前交聯或以其他方式硬化組合物層。
現已發現，本發明的抗反射組合物可在相對較低的溫度下進行交聯或其他硬化（例如55℃、60℃、65℃或70℃，持續30或60秒）。由於此類降低的硬化溫度（起始溫度），已發現硬化的抗反射組合物層的塗層品質得到改善，包括包含親水性樹脂組分的抗反射組合物。在不受任何理論束縛的情況下，改善的塗層品質可能由熱處理過程中組合物樹脂組分的聚集減少引起。
更具體而言，在一個較佳態樣中，提供包含以下的方法： a）在基板上塗覆一層塗料組合物，所述塗料組合物包含：1）樹脂；及2）包含式（I）結構的熱酸產生劑：
Figure 02_image001
其中Y具有式（II）結構：
Figure 02_image003
，每個R1 獨立地為CN、NO2 、F、Cl、Br、I或CF3 ；n為1至5的整數；且X為有機或無機陰離子組分；及 b）在所述塗料組合物層上塗覆一層光致抗蝕劑組合物。
可採用各種陰離子X組分，其包括有機及無機組分，通常較佳為有機組分，諸如甲苯磺酸酯基。在某些態樣中，較佳的R1 基團包括CN、NO2 、Cl、Br、I及CF3 。在另外的態樣中，較佳的R1 基團可為CN、NO2 及CF3 。
本發明的較佳塗料組合物亦可包含單獨的交聯劑組分。此類交聯劑可與樹脂組分反應，諸如在組合物的塗層熱處理過程中，在其上塗覆光致抗蝕劑層之前。
各種樹脂可用於本發明的底層塗料組合物中。在某些實施例中，親水性樹脂為較佳的，諸如聚酯樹脂，包含氰尿酸酯取代的樹脂，包括包含氰尿酸酯取代的聚酯樹脂。較佳地，在此類組合物中，一或多種親水性樹脂占塗料組合物的總樹脂含量的至少50重量%，更佳一或多種親水性樹脂占塗料組合物的總樹脂含量的至少60、70、80、90、95或甚至100重量%。
在與外塗光致抗蝕劑一起使用時，塗料組合物可塗覆於基板上，諸如上面可具有一或多個有機或無機塗層的半導體晶圓。塗覆的塗層可視情況在用光致抗蝕劑層外塗之前經熱處理。如所提及，此類熱處理可引起塗料組合物層硬化，包括交聯。此類交聯可包括硬化及/或一或多種組合物組分之間的共價鍵形成反應且可調節塗料組合物層的水接觸角。
此後，光致抗蝕劑組合物可塗覆於塗料組合物層上方，接著藉由圖案化活化輻射使塗覆的光致抗蝕劑組合物層成像，且使成像的光致抗蝕劑組合物層顯影，得到光致抗蝕劑浮雕圖像。
多種光致抗蝕劑可與本發明的塗料組合物組合使用（即外塗）。與本發明的底層塗料組合物一起使用的較佳光致抗蝕劑為化學放大抗蝕劑，其含有一或多種光敏化合物及含有在光生酸存在下進行去封閉或裂解反應的單元的樹脂組分。
本發明進一步提供塗佈有單獨或與光致抗蝕劑組合物組合的本發明塗料組合物的基板（諸如微電子晶圓基板）。
進一步提供與外塗光致抗蝕劑層一起使用的新型抗反射塗料組合物。較佳的抗反射組合物包含1）樹脂；及2）包含式（IA）結構的熱酸產生劑：
Figure 02_image005
其中Y具有式（IIA）結構：
Figure 02_image007
，每個R1 獨立地為C1 -C6 鹵烷基，諸如CF3 、-CN、-NO2 、-COR2 、-COOR2 、-CONR2 或-SO2 R2 ； R2 獨立地為氫、C1 -C6 烷基、C3 -C6 環烷基或苯基，其可視情況經取代；n為1至5的整數；且X為有機或無機陰離子組分。較佳的式IIA的R1 基團包括-CF3 、-CN及-NO2 、乙醯基及酯。較佳的酯R1 基團在微影處理期間（例如在外塗光致抗蝕劑層的成像的熱處理期間）將不具有反應性（例如將不進行或將顯著地進行鍵斷裂反應）。較佳的X基團為有機組分，諸如甲苯磺酸酯基及其類似基團。
本發明的其他態樣論述於下文中。
在一個較佳的態樣中，提供與外塗光致抗蝕劑組合物一起使用的抗反射組合物，其中所述抗反射組合物包含1）樹脂；及2）包含式（I）結構的熱酸產生劑：
Figure 02_image009
其中Y具有式（IIB）結構：
Figure 02_image011
，每個R1 獨立地為鹵素、C1 -C6 鹵烷基、-CN、-NO2 、-COR2 、-COOR2 、-CONR2 或-SO2 R2 ； R2 獨立地為氫、C1 -C6 烷基、C3 -C6 環烷基或苯基，其可視情況經取代； n為0至5的整數；且 X為有機或無機陰離子組分。
在某些較佳的態樣中，R1 為氟烷基，諸如-CF3 。在較佳的實施例中，如上文所論述，每個R1 獨立地為CN、NO2 、F、Cl、Br、I或CF3 ，或每個R1 獨立地為CN、NO2 、Cl、Br、I或CF3 。各種陰離子X組分適用於有機組分，諸如通常較佳的甲苯磺酸酯基。
在某些實施例中，熱酸產生劑的陽離子組分不含氟作為環取代基。在某些實施例中，熱酸產生劑的陽離子組分不含任何氟含量。在某些實施例中，熱酸產生劑的陽離子組分不含任何鹵素含量。
用於本發明抗反射組合物的較佳熱酸產生劑化合物可具有下式（A），（B）或（C）結構：
Figure 02_image013
。
其中在彼等式（A）、（B）或（C）中的每一者中，R1 為鹵素、C1 -C6 鹵烷基、-CN、-NO2 、-COR2 、-COOR2 、-CONR2 或-SO2 R2 ；且在式（A）、（B）或（C）的某些較佳實施例中，R1 為CN、NO2 、F、Cl、Br、I或CF3 ，且在式（A）、（B）或（C）的其他較佳的實施例中，R1 為CN、NO2 、Cl、Br、I或CF3 ，或R1 為CN、NO2 或CF3 。
用於本發明抗反射組合物的特別較佳的熱酸產生劑包括以下物質。亦較佳的是以下熱酸產生劑，其含有下面描述的經取代的吡啶基陽離子組分，但與除所示的甲苯磺酸酯基之外的陰離子組分複合：
Figure 02_image015
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Figure 02_image017
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Figure 02_image019
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Figure 02_image021
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Figure 02_image023
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Figure 02_image025
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Figure 02_image027
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Figure 02_image029
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Figure 02_image031
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Figure 02_image033
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Figure 02_image035
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Figure 02_image037
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Figure 02_image039
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Figure 02_image041
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Figure 02_image043
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Figure 02_image045
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Figure 02_image047
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Figure 02_image049
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Figure 02_image051
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Figure 02_image053
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Figure 02_image055
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Figure 02_image057
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Figure 02_image059
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Figure 02_image061
、
Figure 02_image063
、
Figure 02_image065
或
Figure 02_image067
。
用於本發明抗反射組合物的尤其較佳的熱酸產生劑包括以下物質。亦較佳的是以下熱酸產生劑，其含有下面描述的經取代的吡啶基陽離子組分，但與除所示的甲苯磺酸酯基之外的陰離子組分複合。
Figure 02_image069
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Figure 02_image071
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Figure 02_image073
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Figure 02_image075
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Figure 02_image077
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Figure 02_image079
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Figure 02_image081
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Figure 02_image083
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Figure 02_image085
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Figure 02_image087
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Figure 02_image089
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Figure 02_image091
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Figure 02_image093
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Figure 02_image095
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Figure 02_image097
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Figure 02_image099
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Figure 02_image101
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Figure 02_image103
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Figure 02_image105
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Figure 02_image107
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Figure 02_image109
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Figure 02_image111
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Figure 02_image113
或
Figure 02_image115
。
有利地，在某些實施例中，所述熱酸產生劑具有不超過約100℃、或不超過約90℃、或不超過約80℃、或不超過約70℃、或不超過約60℃的起始溫度（即熱產生酸時的溫度）。
如本文所提及，熱酸產生劑的起始溫度藉由在選定溫度下對含有熱酸產生劑的旋塗組合物膜層進行熱處理60秒來確定，其中厚度量測值由以下得到：（i）在選定的溫度下進行熱處理的初始旋塗的組合物膜層，及（ii）經有機溶劑（例如50:50 v/v 2-羥基異丁酸甲酯（HBM）:丙二醇甲醚乙酸酯（PGMEA）的有機溶劑）剝離後的組合物膜層。起始溫度為交聯膜的最低溫度，且與最終膜厚度相比，熱處理後評估的含有熱酸產生劑的組合物膜層的厚度減少至少10%。參見實例9的例示性方案。
較佳的TAG具有相對較低的分子量，例如分子量小於或等於3000，更佳≤2500、≤2000、≤1500、≤1000、≤800或甚至更佳≤500。
通常，一或多種熱酸產生劑以組合物的總乾燥組分（除了溶劑載體外的所有組分）的約0.1至10重量%，更佳地，總乾燥組分的約0.5至2重量%的濃度存在於塗料組合物中。
本發明的熱酸產生劑可容易製備。例如，經取代的吡啶基化合物可與陰離子組分混合（例如對於甲苯磺醯基陰離子組分，4-甲基苯磺酸水合物可以與經取代的吡啶基化合物混合）。參見例如以下實例2-4。
本發明的塗料組合物的尤其較佳的樹脂可包含聚酯鍵。聚酯樹脂可藉由一或多種多元醇試劑與一或多種含羧基（諸如羧酸、酯、酐等）化合物進行反應而容易製備。適合的多元醇試劑包括二醇、甘油及三醇，例如二醇，諸如二醇為乙二醇、1,2-丙二醇、1,3-丙二醇、丁二醇、戊二醇、環丁基二醇、環戊基二醇、環己基二醇、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。
較佳地，本發明的底層塗料組合物的樹脂將具有約1,000至約10,000,000道爾頓，更通常約2,000至約10,000道爾頓的重均分子量（Mw）及約500至約1,000,000道爾頓的數均分子量（Mn）。本發明組合物的樹脂的分子量（Mw或Mn）宜藉由凝膠滲透層析法測定。
樹脂組分將為許多較佳實施例中的底層塗料組合物的主要固體組分。舉例而言，一或樹脂宜按塗料組合物的總固體含量計的50至99.9重量%，更通常按塗料組合物的總固體含量計的80或85至95、98或99+（或甚至100）重量%存在。如本文中所提及，塗料組合物的固體係指除了溶劑載體以外的塗料組合物的所有物質。
用於本發明底層塗料組合物的特別較佳的樹脂包括含有下列重複單元的彼等樹脂：
Figure 02_image117
可容易製備用於本發明底層抗反射組合物的合適及較佳的樹脂。參見，例如以下實例1，其中詳述了異氰尿酸酯試劑與二醇化合物反應以提供聚酯氰尿酸酯樹脂。
如上所論述，在某些實施例中，本發明的塗料組合物除樹脂之外或作為樹脂的組分可包含交聯劑。舉例而言，塗料組合物可包括胺基交聯劑，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銷售的樹脂；甘脲，其包括購自氰特工業的彼等甘脲；及基於苯并三聚氰胺（benzoquanamine）及脲的物質，其包括樹脂，諸如以名稱Cymel 1123及1125購自氰特工業的苯并三聚氰胺樹脂及以名稱Powderlink 1174及1196購自氰特工業的脲樹脂。除可商購以外，此類胺基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適合單體共聚來製備。
本發明的塗料組合物（尤其用於反射控制應用）亦可含有吸收用於曝光外塗光致抗蝕劑層的輻射的另外染料化合物。其他視情況選用的添加劑包括表面調平劑，例如可以商品名Silwet 7604購得的調平劑，或購自3M公司的界面活性劑FC 171或FC 431。
本發明的底層塗料組合物亦可含有其他物質，諸如光酸產生劑，其包括如所論述的與外塗光致抗蝕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的此類用途的論述，參見美國專利6261743。
為了製造液態底層塗料組合物，將塗料組合物的組分溶解於適合溶劑中，諸如一或多種氧基異丁酸酯，尤其為甲基-2-羥基異丁酸酯、乳酸乙酯或如2-甲氧基乙醚（二乙二醇二甲醚（diglyme））、乙二醇單甲醚及丙二醇單甲醚的二醇醚中的一或多種；具有醚及羥基部分兩者的溶劑，諸如甲氧基丁醇、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，諸如溶纖劑乙酸甲酯、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，諸如二元酯、碳酸亞丙酯及γ-丁內酯。溶劑中的乾式組分的濃度將取決於若干因素，諸如塗覆方法。一般而言，底層塗料組合物的固體含量在塗料組合物的總重量的約0.5至20重量%範圍內變化，較佳地，固體含量在塗料組合物的約0.5至10重量範圍內變化。光致抗蝕劑
與底層塗料組合物一起使用的光致抗蝕劑通常包含聚合物及一或多種酸產生劑。一般較佳的為正型抗蝕劑且抗蝕劑聚合物具有賦予抗蝕劑組合物鹼性水溶性的官能基。舉例而言，較佳的為包含極性官能基（諸如羥基或羧酸酯基）或在微影處理後可釋放此類極性部分的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的量用於抗蝕劑組合物中。
酸產生劑亦適當地與包含含有芳族基（諸如包括酚的視情況經取代的苯基、視情況經取代的萘基及視情況經取代的蒽）的重複單元的聚合物一起使用。含有視情況經取代的苯基（包括酚）的聚合物尤其適用於多種抗蝕劑系統，包括用EUV及電子束輻射成像的彼等抗蝕劑系統。對於正性作用抗蝕劑，聚合物亦較佳地含有一或多個包含酸不穩定基團的重複單元。舉例而言，在含有視情況經取代的苯基或其他芳族基的聚合物的情況下，聚合物可包含含有一或多個酸不穩定部分的重複單元，諸如藉由使丙烯酸酯或甲基丙烯酸酯化合物的單體與酸不穩定酯（例如丙烯酸第三丁酯或甲基丙烯酸第三丁酯）聚合而形成的聚合物。此類單體可與一或多種包含芳族基（諸如視情況選用的苯基）的其他單體（例如苯乙烯或乙烯基苯酚單體）共聚。
用於形成此類聚合物的較佳單體包括：具有下式（I）的酸不穩定單體，含內酯單體（II）及下式（III）的極性控制單體，或包含前述單體中的至少一種的組合：
Figure 02_image119
其中每個R1 獨立地為H、F、-CN、C1 -6 烷基或C1-6 氟烷基。在式（I）的可酸脫保護的單體中，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 鍵合至相鄰的R2 而形成環狀結構。在式（II）的含內酯單體中，L1 為單環、多環或稠合多環C4-20 含內酯基團。
通式（I）的單元包括酸不穩定基團，其在暴露於活化輻射及熱處理時進行光致酸促進的脫保護反應。此允許改變基質聚合物的極性，導致聚合物及光致抗蝕劑組合物在有機顯影劑中的溶解度發生變化。用於形成式（I）單元的合適單體包括例如以下：
Figure 02_image121
、
Figure 02_image123
、
Figure 02_image125
、
Figure 02_image127
、
Figure 02_image129
、
Figure 02_image131
、
Figure 02_image133
、
Figure 02_image135
、
Figure 02_image137
、
Figure 02_image139
、
Figure 02_image141
、
Figure 02_image143
， 或包含前述單體中的至少一種的組合，其中R1 為H、F、-CN、C1-6 烷基或C1-6 氟烷基。
通式（II）的單元包括有效控制基質聚合物及光致抗蝕劑組合物的溶解速率的內酯部分。用於形成通式（II）單元的合適單體包括例如以下：
Figure 02_image145
、
Figure 02_image147
、
Figure 02_image149
、
Figure 02_image151
、
Figure 02_image153
、
Figure 02_image155
、
Figure 02_image157
、
Figure 02_image159
、
Figure 02_image161
、
Figure 02_image163
， 或包含前述單體中的至少一種的組合，其中R1 為H、F、-CN、C1-6 烷基或C1-6 氟烷基。
式（III）單元提供極性基團，其增強樹脂及光致抗蝕劑組合物的抗蝕刻性，並提供控制樹脂及光致抗蝕劑組合物的溶解速率的另外手段。用於形成式（III）單元的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）。
樹脂可包括一或多種不同於第一單元的通式（I）、（II）及/或（III）的另外單元。當樹脂中存在另外的此類單元時，其較佳包括另外的含離去基團的式（I）單元及/或含內酯的式（II）單元。
除了上述聚合單元之外，樹脂亦可包括一或多種不具有通式（I）、（II）或（III）的另外單元。例如，特別適合的含內酯基的單元具有以下通式（IV）：
Figure 02_image165
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 )伸烷基，且L2 為內酯基。以下例示性單體適用於形成通式（IV）的另外的內酯單元：
Figure 02_image167
、
Figure 02_image169
、
Figure 02_image171
、
Figure 02_image173
、
Figure 02_image175
、
Figure 02_image177
、
Figure 02_image179
， 或包含前述單體中的至少一種的組合，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作用化學放大光致抗蝕劑中的具有酸不穩定的去封閉基團的聚合物已揭示於歐洲專利申請案0829766A2（具有縮醛的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的單元的三元共聚物及其他共聚物）中。
用於本發明光致抗蝕劑中的聚合物的分子量及多分散性可適當地大幅變化。適合的聚合物包括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或更小的彼等聚合物。
較佳的本發明負性作用組合物包含在暴露於酸後將固化、交聯或硬化的物質及兩種或更多種如本文中所揭示的酸產生劑的混合物。較佳的負性作用組合物包含聚合物黏合劑（諸如酚系或非芳族聚合物）、交聯劑組分及本發明的光敏組分。此類組合物及其用途已揭示於Thackeray等人的歐洲專利申請案0164248及美國專利第5,128,232號中。用作聚合物黏合劑組分的較佳酚系聚合物包括酚醛清漆及聚(乙烯基苯酚)，諸如上文所論述的彼等組分。較佳的交聯劑包括胺基物質，包括三聚氰胺、甘脲、苯并胍胺基物質及脲基物質。三聚氰胺-甲醛聚合物通常尤其合適。此類交聯劑為可商購的，例如三聚氰胺聚合物、甘脲聚合物、脲基聚合物及苯并胍胺聚合物，諸如由氰特以商品名Cymel 301、303、1170、1171、1172、1123及1125以及Beetle 60、65及80銷售的彼等交聯劑。
尤其較佳的本發明光致抗蝕劑可用於浸沒式微影應用中。關於較佳浸沒式微影光致抗蝕劑及方法的論述，參見例如羅門哈斯電子材料（Rohm and Haas Electronic Materials）的U.S. 7968268。
本發明的光致抗蝕劑亦可包含單一酸產生劑或相異酸產生劑的混合物，通常2或3種不同酸產生劑的混合物，更通常由總共2種相異酸產生劑組成的混合物。光致抗蝕劑組合物包含以在曝光於活化輻射後足以在組合物的塗層中產生潛像的量採用的酸產生劑。舉例而言，酸產生劑將適當地以按光致抗蝕劑組合物的總固體計，1至20重量%的量存在。
適合的酸產生劑為化學放大光致抗蝕劑領域中已知的且包括例如：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-羥基醯亞胺化合物的磺酸酯衍生物，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；以及含鹵素的三嗪化合物，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。如本文中所提及的酸產生劑化合物亦可稱為光酸產生劑化合物。
本發明的光致抗蝕劑亦可含有其他物質。舉例而言，其他視情況選用的添加劑包括光化及造影染料、抗條紋劑、塑化劑、速度促進劑及敏化劑。此類視情況選用的添加劑通常將以較小濃度存在於光致抗蝕劑組合物中。
或者或另外，其他添加劑可包括淬滅劑，其為非光可破壞鹼，諸如基於氫氧化物、羧酸鹽、胺、亞胺及醯胺的彼等鹼。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）的C1-30 四級銨鹽。例示性淬滅劑包括胺，諸如三丙胺、十二烷胺、三(2-羥丙基)胺、四(2-羥丙基)乙二胺；芳基胺，諸如二苯胺、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，諸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，諸如氫氧化四丁銨（TBAH）或乳酸四丁銨。
界面活性劑包括氟化及非氟化的界面活性劑，且較佳為非離子的。例示性氟化非離子界面活性劑包括全氟C4 界面活性劑，諸如可自3M公司購得的FC-4430及FC-4432界面活性劑；及氟二醇，諸如來自歐諾法（Omnova）的POLYFOX PF-636、PF-6320、PF-656及PF-6520氟界面活性劑。
光致抗蝕劑進一步包括一般適用於溶解、施配及塗佈光致抗蝕劑中所用組分的溶劑。例示性溶劑包括苯甲醚；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的至少一種的組合。 微影處理
在使用中，本發明的塗料組合物藉由諸如旋塗的多種方法中的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致抗蝕劑的製程中的基板。舉例而言，基板可為矽、二氧化矽或鋁-氧化鋁微電子晶圓。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的基板，例如玻璃基板、氧化銦錫塗佈基板等。亦可採用用於光學及光電裝置（例如波導）的基板。
較佳地，塗覆的塗層在光致抗蝕劑組合物塗覆於底層塗料組合物上之前固化。固化條件將隨著底層塗料組合物的組分而有所變化。確切而言，固化溫度將取決於塗料組合物中所用的特定酸或酸（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，如本文中所揭示的較佳抗反射組合物的塗層可以有效地經受在相對較低的溫度，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的光致抗蝕劑溶劑以及顯影劑溶液。
在此類固化之後，將光致抗蝕劑塗覆於塗覆的塗料組合物的表面上。如同底部塗料組合物層的塗覆，外塗光致抗蝕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，光致抗蝕劑塗層通常藉由加熱乾燥以移除溶劑，較佳地直至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光致抗蝕劑層的互混。
抗蝕劑層接著以常規方式經由遮罩用活化輻射，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的光敏組分以在抗蝕劑塗層中產生圖案化圖像。通常，曝光能量的範圍介於約3至300 mJ/cm2 且部分取決於採用的曝光工具及特定抗蝕劑及抗蝕劑處理。曝光的抗蝕劑層可在必要時經受曝光後烘烤以在塗層的曝光與未曝光區域之間產生或增強溶解性差異。舉例而言，負型酸硬化光致抗蝕劑通常需要曝光後加熱以誘導酸促進的交聯反應，且許多化學放大正性作用抗蝕劑需要曝光後加熱以誘導酸促進的脫保護反應。通常，曝光後烘烤條件包括約50℃或更高的溫度，更確切而言，約50℃至約160℃範圍內的溫度。
光致抗蝕劑層亦可曝光於浸沒式微影系統中，亦即其中曝光工具（尤其投影透鏡）與光致抗蝕劑塗佈的基板之間的空間由浸沒流體，諸如水或與一或多種添加劑（諸如可提供增強的折射率的流體的硫酸銫）混合的水佔據。較佳地，浸沒流體（例如水）已經處理以避免氣泡，例如水可經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曝光在此類流體層（例如水或具有添加劑的水）插入在曝光工具與經塗佈的光致抗蝕劑組合物層之間的情況下進行。
曝光的光致抗蝕劑層接著用能夠選擇性地移除膜的一部分以形成光致抗蝕劑圖案的適合顯影劑處理。在負型顯影（NTD）製程中，光致抗蝕劑層的未曝光區域可藉由用適合非極性溶劑處理而選擇性地移除。關於負型顯影的適合程序，參見U.S. 2011/0294069。用於負型顯影的典型非極性溶劑為有機顯影劑，諸如選自酮、酯、烴及其混合物的溶劑，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製程中的光致抗蝕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的水性鹼顯影劑形成正像的光致抗蝕劑層。較佳地，NTD光致抗蝕劑為基於具有酸敏（可脫保護）基團的聚合物，所述基團在脫保護時形成羧酸基及/或羥基。
或者，曝光的光致抗蝕劑層的顯影可藉由用能夠選擇性地移除膜的曝光部分（其中光致抗蝕劑為正型）或移除膜的未曝光部分（其中光致抗蝕劑在曝光區域中可交聯，亦即為負型）的適合顯影劑處理曝光層來實現。較佳地，光致抗蝕劑為正型的，其基於具有在脫保護時形成羧酸基的酸敏（可脫保護）基團的聚合物，且顯影劑較佳地為不含金屬離子的氫氧化四烷基銨溶液，諸如0.26 N氫氧化四甲基銨水溶液。圖案藉由顯影形成。
顯影的基板可接著根據所屬領域中眾所周知的程序在缺乏光致抗蝕劑的彼等基板區域，例如缺乏光致抗蝕劑的化學蝕刻或鍍敷基板區域上選擇性地處理。適合的蝕刻劑包括氫氟酸蝕刻溶液及電漿氣體蝕刻，諸如氧電漿蝕刻。電漿氣體蝕刻移除底層塗層。
如所論述，在某些態樣中，可以適當方式採用濕式蝕刻製程。濕式蝕刻可適當地藉由用濕式蝕刻組合物暴露待蝕刻的表面（例如金屬氮化物，或塗佈有一或多個有機層及/或無機層的金屬氮化物）一定時間及溫度以有效蝕刻表面（例如金屬氮化物表面及/或其上的塗層）來進行。例示性的濕式蝕刻組合物包括氫氧化銨及過氧化物，諸如過氧化氫的水性混合物，或酸，諸如硫酸及過氧化物，諸如過氧化氫的混合物。例示性組合物參見US 2006/0226122。下面的實例亦提供了例示性濕式蝕刻製程條件。如本文所提及，「濕式蝕刻製程」意指用流體組合物處理由鄰接的光致抗蝕劑限定的基板區域（在光致抗蝕劑圖像的顯影之後），所述流體組合物通常為酸性或鹼性的，與過氧化物試劑組合，但在任何情況下與電漿乾式蝕刻不同。
以下非限制性實例為對本發明的說明。 實例1：聚合物合成
Figure 02_image181
如上述方案中所述製備具有結構1重複單元的樹脂，如下所述。將250 ml的3頸圓底燒瓶配備熱電偶、迪安-斯塔克（Dean-stark）裝置、冷凝器及加熱油浴。將三(2-羥乙基)異氰尿酸酯（34.44 g，131.8 mmol）、三(2-羧乙基)異氰尿酸酯（45.50 g，131.8 mmol）、1,2-丙二醇（20.06 g，263.7 mmol）、對甲苯磺酸（p-TSA）（1.00 g，5.3 mmol）及34 g苯甲醚稱重至燒瓶中。將其加熱至設定溫度（150℃）且攪拌40分鐘。然後將溶液冷卻至室溫。將冷卻溶液用三乙胺（0.53 g，5.3 mmol）淬滅，且用HBM（80 g）稀釋以進行分離。用甲基第三丁基醚（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3頸100 ml圓底燒瓶配備熱電偶、冷凝器及加熱油浴。將預聚物（20 g）、p-TSA（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）稱重至燒瓶中且加熱至設定溫度（50℃）並攪拌4小時。用三乙胺（0.5 mL）淬滅溶液。然後將溶液冷卻至室溫。用異丙醇（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2-4：熱酸產生劑的合成 實例2：4-甲基苯磺酸3-氟吡啶-1-鎓的合成
將4-甲基苯磺酸水合物（75.0 g，1.0當量）溶解於四氫呋喃（1500 mL）中，並逐滴添加3-氟吡啶（40.2 g，1.05當量），同時在10〜20℃下劇烈攪拌0.5小時。添加後，將反應混合物在室溫下攪拌16小時。將其過濾且使用四氫呋喃（750 mL）洗滌。將白色固體真空乾燥。 實例3：4-甲基苯磺酸4-氟吡啶-1-鎓的合成
將4-甲基苯磺酸水合物（25.0 g，1.0當量）溶解於四氫呋喃（500 mL）中，並逐滴添加4-氟吡啶（13.4 g，1.05當量），同時在10〜20℃下劇烈攪拌0.5小時。添加後，將反應混合物在室溫下攪拌16小時。將其過濾且使用二乙醚（250 mL）洗滌。將白色固體真空乾燥。 實例4：4-甲基苯磺酸4-(三氟甲基)吡啶-1-鎓的合成.
將4-甲基苯磺酸水合物（6.0 g，1.0當量）溶解於四氫呋喃（120 mL）中，並逐滴添加4-(三氟甲基)吡啶（4.9 g，1.05當量），同時在10〜20℃下劇烈攪拌0.5小時。添加後，將反應混合物在室溫下攪拌16小時。將其過濾且使用二乙醚（60 mL）洗滌。將白色固體真空乾燥。 實例5-8：抗反射組合物的製備 實例5：
將0.863 g聚合物（實例1）、0.027 g作為交聯劑的四甲氧基甲基甘脲及0.010 g作為TAG的4-甲基苯磺酸3-氟吡啶-1-鎓鹽（實例2）溶解於99.0 g HBM溶劑中。 實例6：
將0.863 g聚合物（實例1）、0.027 g作為交聯劑的四甲氧基甲基甘脲及0.010 g作為TAG的4-甲基苯磺酸4-氟吡啶-1-鎓鹽（實例3）溶解於99.0 g HBM溶劑中。 實例7：
將0.860 g聚合物（實例1）、0.027 g作為交聯劑的四甲氧基甲基甘脲及0.013 g作為TAG的4-甲基苯磺酸4-(三氟甲基)吡啶-1-鎓鹽（實例4）溶解於99.0 g HBM溶劑中。 實例8：（比較）
將0.866 g聚合物（實例1）、0.027g作為交聯劑的四甲氧基甲基甘脲及0.007 g作為TAG的4-甲基苯磺酸銨鹽溶解於99.0 g HBM溶劑中。 實例9：抗反射組合物的評估
評估抗反射組合物的與微影用途相關的以下特性：1）塗膜層的厚度，2）首先可能發生組合物膜層硬化的起始溫度，3）組合物膜層覆蓋，4）光學參數，5）組合物的膜層的接觸角，及6）組合物膜層的昇華測試。使用下表1中列出的方案來評估這些特性： 表1：
Figure 107130174-A0304-0001
 結果 第1部分：光學及功能測試性能.
將實例5、6、7及8中的每一個的抗反射組合物的膜層旋塗至矽晶圓上，並如上表1中所述評估伴隨193 nm輻射的光學參數、接觸角及相對昇華度。結果列於下表2中。
表2：193 nm下的n/k值、接觸角及昇華度結果
Figure 107130174-A0304-0002
 第2部分：起始溫度及膜覆蓋結果.
將實例5、6、7及8中的每一個的抗反射組合物的膜層旋塗至矽晶圓上，並如上表1中所述評估起始溫度及膜覆蓋。結果列於下表3中。如表3中所論述，實例5、6及7的抗反射組合物表現出較低的起始溫度（90℃ à60℃）。實例5、6及7的抗反射組合物亦提供與實例8（比較）相比，大大改善的膜覆蓋特性。 表3：利用起始溫度的膜覆蓋結果。
Figure 107130174-A0304-0003

Claims (10)

  1. 一種形成光致抗蝕劑浮雕圖像的方法，所述方法包含：a)在基板上塗覆一層塗料組合物，所述塗料組合物包含：1)樹脂；2)包含式(I)結構的熱酸產生劑：
    Figure 107130174-A0305-02-0028-15
     其中Y具有式(II)結構：
    Figure 107130174-A0305-02-0028-17
    ，每個R1獨立地為F、Cl、Br、I或CF3；n為1至5的整數；且X為陰離子組分，前提是該熱酸產生劑不是對-甲苯磺酸3-氟吡啶鎓；及3)溶劑；及b)在所述塗料組合物層上塗覆一層光致抗蝕劑組合物。
  2. 如申請專利範圍第1項所述的方法，其中至少一個R1為F及/或至少一個R1為CF3及/或X為甲苯磺酸酯。
  3. 如申請專利範圍第1項所述的方法，其中所述熱酸產生劑化合物具有下式(A)、(B)或(C)結構：
    Figure 107130174-A0305-02-0028-14
    Figure 107130174-A0305-02-0028-2
    Figure 107130174-A0305-02-0029-5
     其中，R1如申請專利範圍第1項所定義。
  4. 如申請專利範圍第1項所述的方法，其中式(I)的YH為以下結構中的一個：
    Figure 107130174-A0305-02-0029-11
  5. 一種形成光致抗蝕劑浮雕圖像的方法，所述方法包含：a)在基板上塗覆一層塗料組合物，所述塗料組合物包含：1)樹脂；2)包含式(I)結構的熱酸產生劑：
    Figure 107130174-A0305-02-0029-18
     其中Y具有式(II)結構：
    Figure 107130174-A0305-02-0029-19
    ，每個R1獨立地為鹵素或C1-C6鹵烷基；n為1至5的整數；且X為陰離子組分，前提是該熱酸產生劑不是對-甲苯磺酸3-氟吡啶鎓；及3)溶劑及b)在所述塗料組合物層上塗覆一層光致抗蝕劑組合物。
  6. 如申請專利範圍第1項所述的方法，其中所述塗料組合物包含親水性樹脂。
  7. 一種經塗佈基板，其包含：a)基板，所述基板包含塗覆之塗料組合物，所述塗料組合物包含：1)樹脂；2)包含式(I)結構的熱酸產生劑：
    Figure 107130174-A0305-02-0030-20
     其中Y具有式(II)結構：
    Figure 107130174-A0305-02-0030-21
    ，每個R1獨立地為鹵素或C1-C6鹵烷基；n為1至5的整數；且X為陰離子組分；及3)溶劑及b)所述塗覆之塗料組合物之層上的一層光致抗蝕劑組合物，前提是該熱酸產生劑不是對-甲苯磺酸3-氟吡啶鎓。
  8. 如申請專利範圍第7項所述的基板，其中式(I)的YH為以下結構中的一個：
    Figure 107130174-A0305-02-0030-8
  9. 一種與外塗光致抗蝕劑組合物一起使用的抗反射組合物，所述抗反射組合物包含：1)樹脂；2)包含式(IA)結構的熱酸產生劑：
    Figure 107130174-A0305-02-0030-22
     其中Y具有式(IIA)結構：
    Figure 107130174-A0305-02-0031-9
    ，每個R1獨立地為C1-C6鹵烷基，前提是該熱酸產生劑不是對-甲苯磺酸3-氟吡啶鎓；n為1至5的整數；且X為陰離子組分；及3)溶劑。
  10. 如申請專利範圍第9項所述的抗反射組合物，其中式(IA)的YH為以下結構中的一個：
    Figure 107130174-A0305-02-0031-10
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