TWI251122B - Photoresist composition for deep UV radiation containing an additive - Google Patents

Photoresist composition for deep UV radiation containing an additive Download PDF

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TWI251122B
TWI251122B TW091124341A TW91124341A TWI251122B TW I251122 B TWI251122 B TW I251122B TW 091124341 A TW091124341 A TW 091124341A TW 91124341 A TW91124341 A TW 91124341A TW I251122 B TWI251122 B TW I251122B
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Taiwan
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photoresist
group
photoresist composition
polymer
additive
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TW091124341A
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Takanori Kudo
Ralph R Dammel
Munirathna Padmanaban
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Clariant Int Ltd
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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
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • 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
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • 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
    • G03F7/40—Treatment after imagewise removal, e.g. baking
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/106—Binder containing

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Description

(i) 1251122 玖、發明說明 (發明說明應敘明：發明所屬之技術領域、先前技術、内容、實施方式及圖式簡單說明) 技術領域 本發明係關於一種新穎的光阻組合物，其係於電子或離 子存在下，尤其是於掃描式電子顯微鏡檢查時或於熟化期 間暴露於電子束時，未遭遇到光阻圖像惡化現象。 先前技術 光阻組合物係用於微影製程中，以供製造微型化的電子 元件（例如於電腦晶片及積體電路製程）。一般而言，於這 些方法中，光阻組合物膜的薄塗層係首先塗敷於基板材 料，例如用以製造積體電路之矽晶圓。接著烘烤經塗佈的 基板，以使光阻組合物中任何溶劑蒸發以及使塗層固定於 基板上。塗佈於基板上之光阻接著受到輻射之有關圖像轉 移（image-wise)曝光。 輻射曝光造成塗佈表面之曝光區化學轉換。可見光、紫 外（UV)光、電子束及X-射線輻射能為當前通用於微影製程 之輻射類型。於此有關圖像轉移曝光後，以顯影劑溶液處 理塗佈表面，俾溶解及移除光阻之經輻射曝光或未經曝光 區域。 半導體元件朝微型化之趨勢導致使用對愈來愈低輻射 波長感光之新穎光阻，且亦導致使用複雜的多層系統以克 服與此一微型化有關的困難。 有兩種光阻組合物，正作用型及負作用型。當負作用型 光阻組合物有關圖像轉移曝露於輻射時，曝光於輻射之光 阻組合物區域變得較不溶於顯影劑溶液（例如交聯反應產 發明說明續頁 1251122 (6) 代的聚乙烯等。
以丙稀酸酯為基礎之聚合物通常係以具側脂環基團之 聚（甲基）丙烯酸酯為基礎。側脂環基團之實例可為例如金 剛烷基、三環癸基、異莰基及蓋基。此類聚合物揭示於 R.R. Dammel 等人，Advances in Resist Technology and Processing (抗 蝕劑技術及加工之進展），SPIE，第3333卷，第144頁（1998)。此 等聚合物之實例包含聚（2 -甲基金剛烷基甲基丙烯酸酯-共-甲羥戊酸内酯）、聚（羧基四環十二烷基甲基丙烯酸酯-共-四氫哌喃基羧基四環十二烷基甲基丙烯酸酯）、聚（三 環癸基丙烯酸酯-共-四氫哌喃基曱基丙烯酸酯-共-甲基 丙稀酸S旨）、聚（3 -氧基環己基甲基丙烯酸酯-共-金剛烧基 甲基丙烯酸酯）。
可藉開環置換反應、自由基聚合反應或使用金屬無機觸 媒，使合成自環烯烴（具正冰片烯及四環十二烯衍生物） 之聚合物聚合。亦可以馬來酸酐或以馬來醯亞胺或其衍生 物，使環稀烴衍生物共聚合。此類聚合物係揭示於以下文 獻中且合併於本案以供參考·· M-D. Rahman等人，Advances in Resist Technology and Processing (抗 I虫劑技術及力口工之進展）， SPIE，第3678卷，第1193頁（1999)。此等聚合物之實例包含聚（第 三丁基5-正冰片烯-2-羧酸酯-共-2 -羥乙基5-正冰片烯-2-羧酸酯-共-5 -正冰片烯-2 -羧酸-共-馬來酸酐）、聚（第三丁 基5 -正冰片烯_ 2 -羧酸酯-共-異莰基-5 -正冰片烯-2 -羧酸酯 -共-2 -經乙基5-正冰片婦-2-魏酸醋-共-5-正冰片稀-2-叛 酸-共-馬來酸酐）、聚（四環十二烯-5 -羧酸酯-共-馬來酸酐） -11 - 發明說明續頁 1251122 (7) 及其類似物。 合併本發明所揭示之添加劑，於157毫微米曝光有效的 氟化的非酚系聚合物亦展現LWS及優勢。此類聚合物揭示 於W0 00/17712及W0 00/67072中，並且合併於本案以供參考。 一種此類聚合物之貫例為聚（四氣乙稀-共-正冰片稀-共_ 5 -六氟異丙醇取代的2-正冰片烯）。 自環烯烴及含氰基的乙烯系單體合成之聚合物揭示於 美國專利申請案第09/854,312號，並且合併於本案以供參 考。 聚合物之分子量係以所用的化學類型及以所需的微影 效能為基礎。通常，重量平均分子量係在3,000至30,000之範 圍内，且多分散度係在1.1至5(較佳為1.5至2.5)之範圍内。 酸產生光敏性化合物之適合的實例包含鍚鹽，例如重氮 鹽、錤鹽、锍鹽、鹵化物及酯類（雖然可使用任何當照光 時產生酸之光敏性化合物）。鍚鹽通常係以溶解於有機溶 劑中之形式使用，大部分作為錤鹽或锍鹽，其實例為三氟 甲烷磺酸二苯基鎭、九氟丁烷磺酸二苯基鎭、三氟曱烷磺 酸三苯基锍、九氟丁烷磺酸三笨基锍及其類似物。可使用 其他當照光時形成酸之化合物，例如三嗪、噚唑、噚二唑、 噻唑、經取代的2 -吼喃酮。酚系磺酸酯、雙-磺基甲烷、 雙-磺基甲烷或雙-丁基重氮甲烷亦較佳。 合併於本發明光阻之特殊添加劑係為防止光阻圖像當 暴露於電子或離子環境時惡化之添加劑。意外地發現某些 添加劑可降低光阻圖像惡化情形（當於掃描式電子顯微鏡 1251122 (9) 藉光阻技藝中所用的任何已知方法（含浸潰 旋及旋轉塗佈），所製得的光阻組合物溶液 板。當例如旋轉塗佈時，可相對於固形物含量 整光阻溶液，俾提供具所需厚度之塗層（假使 設備及時間量容許進行旋轉法）。適合的基板g 聚合樹脂、二氧化矽、摻雜的二氧化矽、氮化/ 聚矽、陶瓷、鋁/銅混合物；砷化鎵及其他第 物。光阻亦可塗佈於抗反射層上。 藉所述之程序製得的光阻塗層特別適合應， 化矽晶圓（其係用於製造微處理器及其他小型 件）。亦可使用鋁/氧化鋁晶圓。基板亦可含有 脂，尤其是透明的聚合物，例如聚S旨類。 接著將光阻組合物溶液塗佈於基板上，並且 度為約70°C至約150°C在加熱板上處理約30秒至 於對流烘箱中處理15至約90分鐘。選擇此溫度 光阻中之殘餘溶劑濃度，而不會造成固體成分 裂解。一般而言，必須使溶劑的濃度減至最 度。進行處理直到幾乎所有溶劑蒸發以及光阻 (厚度約半微米）保留於基板上為止。在一個較 例中，溫度係為約95°C至約120°C。進行處理 除速率變為相當不明顯為止。溫度及時間選擇 用者所欲的光阻性質以及所用的設備及商業 佈時間。接著可以任何所欲的圖案（藉使用適 陰極、模板、樣板等製得）有關圖像轉移曝光 發明說明績頁 、噴淋、迴 可施敷至基 之百分比調 所用的旋轉 L含矽、鋁、 5夕、组、銅、 III/V族化合 雨於矽/二氧 積體電路元 許多聚合樹 使基板於溫 約180秒，或 處理以降低 大體上的熱 小及此初溫 溶液之薄層 佳具體實施 直到溶劑移 係取決於使 上所需的塗 合的罩幕、 於光化輻射 -14- 1251122 _ (13) 發明說明續頁 例1中所述的方法處理。於劑量28 mJ/cm2下得到0.14微米之 線解析度。 實例3 將0.01725克四曱氧基曱基甘脲溶解於30克比較例1中製 備的光阻中。使用0.2微米濾器過濾光阻溶液，並且以類 似比較例1中所述的方法處理。於劑量66 mJ/cm2下得到0.14 微米之線解析度。 實例4 將0.0135克9-蒽甲醛溶解於20克比較例2中製備的光阻 中。使用0.2微米遽器過濾、光阻溶液，並且以類似比較例2 中所述的方法處理。於劑量18.5 mJ/cm2下得到0.08微米之線 解析度。 實例5 將0.0237克1,4-二碘四氟苯溶解於20克比較例2中製備的 光阻中。使用0.2微米濾器過濾光阻溶液，並且以類似比 較例2中所述的方法處理。於劑量18 mJ/cm2下得到0.10微米 之線解析度。 實例6 將5.89克聚合物（製自100份馬來酸酐、35份5-正冰片烯-2 -羧酸第三丁基酯、1 0份5 -正冰片烯-2 -羧酸2 -羥乙基酯、 5份5 -正冰片烯-2 -羧酸、2 5份2 -曱基金剛烷基甲基丙烯酸 酯及25份甲基丙烯酸2 -甲羥戊酸内酯）、0.154克九氟丁烷 磺酸二苯基錤、2.80克1重量％三辛基胺之PGMEA(丙二醇 單甲基醚醋酸酯）溶液及0.054克10重量％界面活性劑之 1251122 發明說明讀頁 (15) 如表1所示，於CD SEM中30秒檢驗時間後，無添加劑之 光阻（如比較例1及2)展現超過1 0 %之臨界尺度減少率。然 而，當於相同條件下處理時，本發明新穎的光阻保留超過 9 1 %之臨界尺度。最小的臨界尺度減少率是較佳的。此臨 界尺度減少率較佳為小於1 0 %。
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Claims (1)

1251122 #091124341號專利申請案 中文申請專利範圍替換本(94年11月） 拾、申請專利範圍 1 . 一種光阻組合物，其適用於低於2 0 0毫微米下曝光且可 降低電子及離子對光阻惡化之影響，其係包含： a) —種不溶於鹼性水溶液且含有至少一個對酸不穩定 的基團之聚合物，並且該聚合物大體上為非芳香族 的； b) —種當輻射時可產生酸之化合物；及 c) 0.1至5重量％添加劑，其係選自由|昆類、經取代的酉昆 類、蒽、蒽曱醇、E甲醛、甘脲及經碘取代的芳香族 化合物組成之群。 2 .如申請專利範圍第1項之光阻組合物，其中該添加劑係 選自由蒽、蒽甲醇、蒽甲醛、氫醌、第三丁基氫醌、甘 脲及碘取代的苯所組成之群。 3 .如申請專利範圍第1項之光阻組合物，其中該添加劑係 選自由9-E甲醇、9_蒽甲醛、四曱氧基曱基甘脲及1，4-二蛾四氟苯所組成之群。 4 .如申請專利範圍第1項之光阻組合物，其中該聚合物含 有脂環族基團。 5 ·如申請專利範圍第4項之光阻組合物，其中該聚合物含 有具側脂環族基團之丙烯酸酯主鏈。 6 .如申請專利範圍第4項之光阻組合物，其中該聚合物具 有脂壤族基團之主鍵。 7 .如申請專利範圍第4項之光阻組合物，其中該聚合物係 為馬來酸酐與經取代及/或未經取代的脂環族單體之共 聚合物。
1251122 8。如申請專利範圍第1項之光阻組合物，其中該聚合物不 含芳香族基團。 9 · 一種形成光阻圖像之方法，其包含下列步驟： a) 於具如申請專利範圍第1項之光阻組合物之基板上形成 塗層，及於70°C至150°C烘烤該塗層歷時30秒至90分鐘； b) 使該光阻塗層於小於200毫微米之波長下進行有關圖 像轉移（imagewise)曝光；及 c) 以含氫氧化四甲基銨之水性鹼顯影劑使該光阻塗層 顯影。 10.如申請專利範圍第9項之方法，其中該有關圖像轉移曝 光係於波長193毫微米或157毫微米下進行。 1L如申請專利範圍第9項之方法，尚包含電子熟化步驟。 12.如申請專利範圍第9項之方法，尚包含於掃描式電子顯 微鏡中檢驗該光阻圖像。
TW091124341A 2001-11-07 2002-10-22 Photoresist composition for deep UV radiation containing an additive TWI251122B (en)

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EP (1) EP1444551B1 (zh)
JP (1) JP2005508527A (zh)
KR (1) KR20050056913A (zh)
CN (1) CN1306340C (zh)
AT (1) ATE299275T1 (zh)
DE (1) DE60204980T2 (zh)
MY (1) MY130283A (zh)
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WO (1) WO2003040826A1 (zh)

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