TWI510862B - 抗反射塗層組合物及其方法 - Google Patents
抗反射塗層組合物及其方法 Download PDFInfo
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- TWI510862B TWI510862B TW099143805A TW99143805A TWI510862B TW I510862 B TWI510862 B TW I510862B TW 099143805 A TW099143805 A TW 099143805A TW 99143805 A TW99143805 A TW 99143805A TW I510862 B TWI510862 B TW I510862B
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Classifications
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- 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
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
- H01L21/0276—Photolithographic processes using an anti-reflective coating
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
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- 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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- C08G2261/10—Definition of the polymer structure
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- C08G2261/141—Side-chains having aliphatic units
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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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- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
- C08G2261/1422—Side-chains containing oxygen containing OH groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/42—Non-organometallic coupling reactions, e.g. Gilch-type or Wessling-Zimmermann type
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- C08G2261/50—Physical properties
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- Condensed Matter Physics & Semiconductors (AREA)
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- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Architecture (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Materials For Photolithography (AREA)
- Paints Or Removers (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
本發明係關於一種包括聚合物之吸收硬遮罩抗反射塗層組合物,其中該聚合物包括在該聚合物主鏈中之至少一種苯基單元及至少一種經取代或未經取代之芳族稠合環,及一種利用該抗反射塗層組合物形成影像之方法。該方法尤其適用於利用在深及極紫外(uv)區域中輻射使光阻劑成像。
光阻劑組合物係用於製造小型化電子組件之微蝕刻製程中,諸如在製造電腦晶片及積體電路中。一般而言,在此等製程中,首先係將光阻劑組合物的薄膜之薄層施加至基板材料上,諸如用於製造積體電路之以矽為主之晶圓。隨後將經塗佈之基板烘烤以蒸發該光阻劑組合物中之任何溶劑及使該塗層固定於該基板上。繼而對該基板之經烘烤塗佈之表面施以成像輻射暴露。
此輻射暴露在經塗佈表面之暴露區域中引起化學轉變。可見光、紫外(UV)光、電子束及X-射線輻射能係目前用於微蝕刻製程中之常見輻射類型。在此成像暴露之後,將經塗佈之基板用顯影劑溶液處理以溶解及移除光阻劑之經輻射暴露或未經暴露區域。
半導體裝置之小型化趨勢已導致使用對愈來愈低波長的輻射敏感之新穎光阻劑,及亦已導致使用多級精密系統,以克服與該小型化相關之困難。
在微影中吸收抗反射塗層及底層係用來減少自高反射基板之光的背反射所產生之問題。背反射率之兩個主要的缺點在於薄膜干涉效應及反射刻痕。薄膜干涉或駐波會造成臨界線寬度尺寸變化,其係由隨著光阻劑厚度變化而造成光阻劑薄膜中總光強度之變化引起,或反射及入射暴露輻射之干涉可引起扭曲通過該厚度之輻射均勻性之駐波效應。當光阻劑係於包含表面構形之反射基板上圖案化時反射刻痕變得嚴重,其散射光通過光阻劑薄膜從而導致線寬度變化,且在極端的情況下,形成光阻劑完全損失之區域。塗佈在光阻劑以下及反射基板以上之抗反射塗層可在光阻劑蝕刻性能中提供顯著改良。通常係將底部抗反射塗層施加至基板及隨後將光阻劑層施加至該抗反射塗層之上。抗反射塗層經固化以防止該抗反射塗層與該光阻劑之間的混合。光阻劑經暴露成像及顯影。隨後通常利用不同的蝕刻氣體使經暴露區域中之抗反射塗層經乾式蝕刻,因此將光阻劑圖案轉移至基板。多層抗反射層及底層係用於新蝕刻技術。在光阻劑並不提供充分的抗乾式蝕刻性的情況中,以充當硬遮罩及在基板蝕刻期間具有高度抗蝕刻性的光阻劑之底層或抗反射塗層較佳,且已發現一種將矽併入有機光阻劑層下方之層中之方法。此外,另一高含碳量之抗反射或遮罩層係經添加至矽抗反射層下方,其係用於改善成像製程之蝕刻性能。該矽層可經旋塗或藉由化學氣相沈積法沈積。矽在使用O2
蝕刻之製程中係高度抗蝕刻的,且藉由在矽抗反射層下方提供具有高含碳量之有機遮罩層可獲得相當大的縱橫比。因此,有機高碳遮罩層可比其上之光阻劑或矽層厚很多。有機遮罩層可用作比起初光阻劑更厚的薄膜及可提供更好的基板蝕刻遮罩。
本發明係關於一種具有高含碳量之新穎有機旋塗抗反射塗層組合物或有機遮罩底層,且其可在光阻劑層與該基板之間用作多層之一者之單層。通常,該新穎組合物可用於形成一位於基本上抗蝕刻之抗反射塗層下方之層,諸如矽抗反射塗層。該新穎抗反射塗層(亦稱為碳硬遮罩底層)中之高含碳量可提供具有高縱橫比之高解析度影像轉移。該新穎組合物係用於使光阻劑成像,及亦係用於蝕刻該基板。該新穎組合物能夠自該光阻劑很好地影像轉移至該基板,且亦減少反射及增強圖案轉移。此外,該抗反射塗層與其上塗佈之薄膜之間大體上不出現混合。該抗反射塗層亦具有良好的溶液穩定性並形成具有良好的塗佈品質之薄膜,後者對蝕刻技術特別有利。
本發明係關於一種包括交聯劑及能夠藉由該交聯劑交聯之可交聯聚合物之抗反射塗層組合物,其中該可交聯聚合物包括由結構(1)表示之單元:
其中A係稠合芳族環及B具有結構(2),
其中R1
係C1
-C4
烷基及R2
係C1
-C4
烷基。
本發明進一步係關於一種利用該組合物形成影像之方法。
本發明係關於一種包括交聯劑及能夠經由該交聯劑交聯之可交聯聚合物之吸收抗反射塗層組合物,其中該聚合物包括在該聚合物主鏈中之至少一種含苯基之單元及在該聚合物主鏈中之至少一種稠合芳族單元。本發明亦係關於一種使經塗佈於新穎抗反射塗層上之光阻劑層成像之方法。
本發明之新穎抗反射組合物包括能夠交聯的具有高含碳量之新穎聚合物,以使得交聯之後自該組合物所形成之塗層變得不可溶於經塗佈於其上之材料的溶劑中。該新穎塗層組合物能夠自身交聯或可另外包括能夠與該聚合物交聯之交聯化合物。該組合物可另外包括其他添加劑,諸如有機酸、酯、熱酸產生劑、光酸產生劑、界面活性劑、其他高含碳量聚合物等。該組合物可包括其他聚合物,尤其係彼等具有高含碳量者。新穎組合物之固體組分係經溶於包含一或多種有機溶劑之有機塗層溶劑組合物中。該新穎聚合物可溶於有機塗層溶劑中。
新穎組合物之聚合物在該聚合物主鏈中包括至少一種稠合芳族基團單元及至少一種含苯基基團之單元。該聚合物可由結構1表示:
其中A係稠合芳族環基團及B具有結構(2),
其中R1
係C1
-C4
烷基及R2
係C1
-C4
烷基。該稠合芳族基團包括2或更多個稠合在一起之芳族單元。該稠合芳族基團可包括2至8個芳族環或2至6個芳族環或3至5個芳族環或3至4個芳族環。該稠合芳族環可包括3個芳族環。該稠合芳族環可為蒽基。
該新穎聚合物可在酸觸媒的存在下,藉由含苯基基團之單體與含稠合芳族基團之單體之縮合反應獲得。該聚合物中稠合芳族基團包括經取代或未經取代之稠合芳族環。該聚合物之稠合芳族環可包括2至8員芳族環。稠合芳族基團之實例係以下結構3至14。
儘管該單元可係如結構3至14所示,但稠合環可在該芳族結構中任何位置上形成聚合物之主鏈且附接位置可在該聚合物內變化。該稠合環結構可具有形成分支寡聚物或分支聚合物之2個以上的附接點。在該聚合物之一實施例中,該稠合芳族單元係經連接至另一芳族碳基團或另一稠合芳族單元。可形成稠合芳族單元之嵌段物且該等嵌段物可藉由諸如亞甲基之飽和脂族碳單元分離。
聚合物之稠合芳族環可未經取代或經一或多種有機成份取代,諸如烷基、經取代之烷基、芳基、經取代之芳基、烷基芳基及鹵烷基、羥基、胺基、胺基烷基、烷氧基,諸如甲基、胺基甲基、溴甲基、及氯甲基基團。可存在多達4個取代基。芳族環上之取代基可有助於提高聚合物在塗層溶劑中之溶解度。稠合芳族結構上之某些取代基亦可在固化期間熱分解,以使得其等不會殘留於固化塗層中並因此在蝕刻製程期間提供有用的高含碳量。
該聚合物可包括一種以上類型的文中所述之稠合芳族結構。在一實施例中,該稠合芳族基團係未經取代。在一實施例中,該稠合芳族基團不含羥基或烷氧基基團。在另一實施例中,該稠合芳族基團A及苯基基團B係未經取代,其僅經氫取代。
除稠合環單元外,新穎抗反射塗層之聚合物進一步包括含苯基之至少一種單元B(顯示於結構1中)。該單元B可衍生自包括2個不飽和基團之單體,諸如烷基經取代或未經取代之二乙烯基苯。該聚合物包括單元-(A)-及-(B)-,其中A係先前所述之任何稠合芳族單元,其可為直鏈或分支鏈、經取代或未經取代且其中B係苯基基團,其係經由飽和碳連接至A,如結構2中所示。
芳基或芳族基團包含6至24個碳原子,其包括苯基、甲苯基、二甲苯基、萘基、蒽基、聯苯基、雙-苯基、參-苯基及類似物。此等芳基基團可進一步經任何適宜的取代基取代,例如上文中所提及之烷基、烷氧基、醯基或芳基。同樣地,所希望之適宜的多價芳基基團可用於本發明中。二價芳基之代表性實例包括伸苯基、苯二甲基、伸萘基、聯伸苯基及類似物。烷氧基意指具有1至20個碳原子之直鏈或分支鏈烷氧基且包括(例如):甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第三丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基、癸氧基、4-甲基己氧基、2-丙基庚氧基、及2-乙基辛氧基。芳烷基意指具有附接的取代基之芳基。該等取代基可為任何取代基,諸如烷基、烷氧基、醯基等。具有7至24個碳原子之單價芳烷基之實例包括苯甲基、苯乙基、二苯甲基、1,1-或1,2-二苯乙基、1,1-、1,2-、2,2-、或1,3-二苯丙基及類似物。如文中所述具有所希望化合價之經取代之芳烷基之適宜組合物可用作多價芳烷基基團。
在一實施例中,該新穎聚合物係不含任何脂族環狀或多環基團,諸如環己基、金鋼烷基、冰片基等。在另一實施例中,該新穎聚合物係不含任何脂族環狀或多環基團、羥基或烷氧基基團。在一實施例中,該組合物中無聚合物包括脂族多環基團,諸如等環己基、金鋼烷基、冰片基等。
本發明新穎組合物之聚合物可藉由在酸觸媒的存在下使以下物質反應而合成:a)至少一種芳族化合物,其包括2或更多種能夠進行親電子取代之稠合芳族環,以使得該等稠合環形成聚合物之主鏈,與b)至少一種芳族單元,其具有兩個可形成碳陽離子之活性位置。該芳族化合物可選自提供所希望之芳族單元之單體,更特定言之以上所示之結構或等效物,及可另外選自諸如蒽、菲、芘、螢蒽、三伸苯基蔻、蒽甲醇、甲基甲氧基蒽等之化合物。該等稠合芳族環提供至少2個可用於親電子取代之反應位置。
用於形成新穎聚合物中的單元B之單體包括苯基單元,其具有能夠在酸的存在下形成碳陽離子之兩個反應位置,及可選自諸如二乙烯基苯之化合物。該反應係在強酸(諸如磺酸)的存在下催化。可使用任何磺酸,其實例為三氟甲磺酸、九氟丁磺酸、雙全氟烷基醯亞胺、參全氟烷基碳化物、或其他強非親核性酸。該反應可用或不用溶劑實施。若使用溶劑,則可使用能夠溶解固體組分之任何溶劑,尤其係彼等不與強酸反應者;可使用諸如氯仿、雙(2-甲氧基乙基醚)、硝基苯、二氯甲烷、及二乙二醇二甲醚、三乙二醇二甲醚、二(乙二醇)二甲基醚、二(乙二醇)二乙基醚、二(丙二醇)二甲基醚、二(丙二醇)二乙基醚、丙二醇單甲基醚醋酸酯(PGMEA)、丙二醇單甲基醚(PGME)之溶劑。可在適宜的溫度下將反應混合一段適宜的時間,直至形成聚合物為止。反應時間可在約3小時至約24小時的範圍內,及反應溫度可在約80℃至約180℃的範圍內。在適宜的溶劑(諸如甲醇、己烷、庚烷)中經由沉澱及沖洗以將聚合物隔離及純化。該新穎聚合物可經分餾以獲得具有所希望分子量之餾分。將該聚合物溶於溶劑中,例如四氫呋喃(THF);將非溶劑添加至溶液中,諸如烷烴;及形成沉澱物並將其過濾。可在室溫下進行分餾製程。可將聚合物進一步純化。通常移除低分子量部份。可利用先前已知之反應、隔離及純化該聚合物之技術。該聚合物之重量平均分子量可在約1200至約5,000,或約1300至約3,000或約1,500至約2,600的範圍內。
聚合物之折射係數,n(折射率)及k(吸收率),在所用暴露波長處(諸如193 nm),折射率可在約1.3至約2.0的範圍內且吸收率可在約0.05至約1.0的範圍內。該聚合物或組合物的含碳量係藉由對固體組合物進行元素分析而測定。組合物或聚合物之含碳量可在基板上形成塗層及使薄膜乾燥之後測量。對固體塗層或乾燥聚合物進行元素分析可提供以重量%計之含碳量。根據元素分析測定,聚合物或組合物在交聯之後的含碳量係大於80重量%,或大於85重量%,或大於90重量%。在一實施例中,聚合物在交聯之後的含碳量係在80至95重量%的範圍內。
本發明新穎組合物之聚合物可具有如結構(15)中所示之結構單元,其中R1
及R2
係如先前所述。
本發明之新穎組合物包括聚合物及進一步可包括交聯劑。通常,該交聯劑係一種能充當親電子劑之化合物且可單獨或在酸的存在下形成碳陽離子。因此,包含諸如醇、醚、酯、烯烴、甲氧基甲基胺基、甲氧基甲基苯基及包含多個親電子位置之其他分子之基團之化合物能夠與該聚合物交聯。可使用聚合物交聯劑,諸如甘脲、三聚氰胺等之聚合物。可作為交聯劑之化合物之實例係1,3-金剛烷二醇、1,3,5-金剛烷三醇、多官能反應性苄基化合物、結構(16)之四甲氧基甲基-雙酚(TMOM-BP)、胺基樹脂交聯劑、甘脲、Cymel、Powderlink等。
包含該聚合物之新穎組合物亦可包括酸產生劑及視需要包括交聯劑。該酸產生劑可為能夠在加熱時產生強酸之熱酸產生劑。用於本發明中之熱酸產生劑(TAG)可為在加熱時產生酸之任何一或多種熱酸產生劑,該酸可與聚合物反應並增長本發明中所存在之該聚合物之交聯,其特別佳係一種諸如磺酸之強酸。較佳地,熱酸產生劑係在90℃以上活化,較佳在120℃以上,及甚至更佳在150℃以上。熱酸產生劑之實例係不含金屬之鋶鹽及碘鎓鹽,諸如強非親核性酸之三芳基鋶、二烷基芳基鋶、及二芳基烷基鋶鹽;強非親核性酸之烷基芳基碘鎓、二芳基碘鎓鹽;及強非親核性酸之銨、烷基銨、二烷基銨、三烷基銨、四烷基銨鹽。同樣,亦可將共價熱酸產生劑作為有用的添加劑,例如烷基或芳基磺酸之2-硝基苄基酯及可經熱分解得到游離磺酸之磺酸之其他酯。實例係二芳基碘鎓全氟烷基磺酸酯、二芳基碘鎓參(氟烷基磺醯基)甲基化物、二芳基碘鎓雙(氟烷基磺醯基)甲基化物、二芳基碘鎓雙(氟烷基磺醯基)醯亞胺、二芳基碘鎓四級銨全氟烷基磺酸酯。不穩定酯之實例係:甲苯磺酸2-硝基苄酯、甲苯磺酸2,4-二硝基苄酯、甲苯磺酸2,6-二硝基苄酯、甲苯磺酸4-硝基苄酯;苯磺酸酯,諸如2-三氟甲基-6-硝基苄基4-氯苯磺酸酯、2-三氟甲基-6-硝基苄基4-硝基苯磺酸酯;酚系磺酸酯,諸如苯基、4-甲氧基苯磺酸酯;四級銨參(氟烷基磺醯基)甲基化物、及四級烷基銨雙(氟烷基磺醯基)醯亞胺、有機酸之烷基銨鹽,諸如10-樟腦磺酸之三乙銨鹽。各種芳族(蒽、萘或苯衍生物)磺酸胺鹽可用作TAG,其包括彼等美國專利第3,474,054號、第4,200,729號、第4,251,665號及第5,187,019號中所揭示者。TAG較佳在170至220℃之間的溫度下具有極低的揮發性。TAG之實例係由King Industries以Nacure及CDX商品名售出者。該等TAG係Nacure 5225、及CDX-2168E,其係來自King Industries,Norwalk,Conn. 06852,USA之以丙二醇甲基醚中25-30%活性提供之十二烷基苯磺酸胺鹽。
該新穎組合物可進一步包含至少一種已知光酸產生劑,其實例係(但不限於)鎓鹽、磺酸酯化合物、硝基苄基酯、三嗪等。較佳的光酸產生劑係羥基醯亞胺之鎓鹽及磺酸酯,特定言之係二苯基碘鎓鹽、三苯基鋶鹽、二烷基碘鎓鹽、三烷基鋶鹽、及其混合物。此等光酸產生劑未必經光解而是經熱分解以形成酸。
本發明之抗反射塗層組合物可包含佔該組合物中總固體之1重量%至約30重量%的新穎稠合芳族聚合物,及較佳為4重量%至約15重量%。當用於組合物中時,交聯劑可以佔總固體之約1重量%至約30重量%。熱酸產生劑可併入約0.1至約10重量%範圍內的抗反射塗層組合物之總固體,較佳為0.3至5重量%的固體,及更佳為0.5至2.5重量%的固體。
該新穎組合物可進一步包括第二聚合物。該第二聚合物可為亦具有含碳量大於75重量%,或大於80重量%者。該第二聚合物可包括文中所述之含稠合芳族環之單元A、苯基基團B、及選自具有大於2個芳族環之經取代之稠合芳族環之第三單元。第三單元可選自經羥基取代之稠合芳族單元。第三單元可選自羥基蒽基基團、羥基苯基基團、羥基萘基基團、羥基芘基基團、C1
-C4
烷氧基蒽基基團、C1
-C4
烷基苯基基團、C1
-C4
烷基萘基基團、C1
-C4
烷基芘基基團等。第三單元可選自羥基苯基、羥基萘基、羥基菲基、羥基蒽基等。第三單元可為羥基萘基。第二聚合物可以該組合物中1重量%至20重量%範圍內的總聚合物濃度,或1重量%至10重量%範圍內之總聚合物濃度添加至該組合物中。在一實施例中,第二聚合物不含任何脂族環狀多環基團。在另一實施例中,第二聚合物係不含任何脂族環狀多環基團及第三單元係羥基萘基基團。
在一實施例中,該新穎組合物包括新穎聚合物、文中所述之第二聚合物、交聯劑、熱酸產生劑、視需要之界面活性劑及溶劑。
抗反射塗層組合物之固體組分係與溶解該抗反射塗層之固體組分之溶劑或溶劑之混合物混合。適用於抗反射塗層組合物之溶劑可包括(例如)二醇醚衍生物,諸如乙氧乙醇、甲氧乙醇、丙二醇單甲基醚、二乙二醇單甲基醚、二乙二醇單乙基醚、二丙二醇二甲基醚、丙二醇正丙基醚、或二乙二醇二甲基醚;二醇醚酯衍生物,諸如醋酸乙氧乙酯、醋酸甲氧乙酯或丙二醇單甲基醚醋酸酯;羧酸酯,諸如醋酸乙酯、醋酸正丁酯及醋酸戊酯;二鹽基酸之羧酸酯,諸如二乙氧基酯及二乙基丙二酸酯;二醇之二羧酸酯,諸如乙二醇二醋酸酯及丙二醇二醋酸酯;及羥基羧酸酯,諸如乳酸甲酯、乳酸乙酯、乙基乙二醇酯及乙基-3-羥基丙酸酯;酮酯,諸如丙酮酸甲酯或丙酮酸乙酯;烷氧基羧酸酯,諸如3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、或甲基乙氧基丙酸酯;酮衍生物,諸如甲基乙基酮、乙醯基丙酮、環戊酮、環己酮或2-庚酮;酮醚衍生物,諸如二丙酮醇甲基醚;酮醇衍生物,諸如丙酮醇或二丙酮醇;內酯,諸如丁內酯;及醯胺衍生物,諸如二甲基乙醯胺或二甲基甲醯胺、苯甲醚及其混合物。
該抗反射塗層組合物可包括其他組分以增強該塗層之性能,例如單體染料、低碳醇(C1
-C6
醇)、表面均染劑、黏著促進劑、消泡劑等。
由於抗反射薄膜係塗佈於基板之上且亦受乾式蝕刻,因此可假定該薄膜具有不負面影響半導體裝置性質之足夠低的金屬離子濃度及足夠的純度。處理(諸如使聚合物溶液通過離子交換管柱、過濾及萃取製程)可用於降低金屬離子濃度及減少顆粒。
新穎組合物之吸收參數(k)得自橢圓偏光測量在暴露波長處係在約0.05至約1.0的範圍內,較佳為約0.1至約0.8。在一實施例中,該組合物在暴露波長處具有約0.2至約0..5範圍內之k值。該抗反射塗層之折射率(n)亦係經最佳化且可在約1.3至約2.0的範圍內,較佳為1.5至約1.8。可使用橢圓偏光計,諸如J. A. Woollam WVASE VU-32TM
橢圓偏光計計算n及k值。k及n的最佳範圍之確切值係取決於所用暴露波長及應用類型。通常,對於193 nm,k之較佳範圍係約0.05至約0.75,及對於248 nm,k之較佳範圍係約0.15至約0.8。
根據自組合物所製造之乾燥薄膜之元素分析測定,新穎抗反射塗層組合物之含碳量係大於80重量%或大於85重量%。甚至在來自該新穎組合物之薄膜已經加熱至高達400℃的溫度長達120秒後,自該組合物衍生之薄膜的含碳量係保持在80重量%或大於80重量%的含量。
使用熟悉此項技術者所熟知之技術(諸如浸塗、旋塗或噴塗)將抗反射塗層組合物塗佈於基板上。該抗反射塗層之薄膜厚度係在約15 nm至約400 nm的範圍內。該塗層可於熱板或對流烘箱上進一步加熱充分長的時間,以移除任何殘餘的溶劑及誘發交聯,並藉此使該抗反射塗層不能溶解,從而防止抗反射塗層與待塗佈於其上之層之間的混合。溫度的較佳範圍係約90℃至約280℃。
可將其他類型的抗反射塗層塗佈於本發明之塗層上。通常,使用具有高抗氧蝕刻性之抗反射塗層(諸如含矽基者,諸如矽烷、官能性矽氧烷、半矽氧烷或減少蝕刻速率之其他基團等),以使得該塗層可充當圖案轉移之硬遮罩。該矽塗層可經旋塗或化學氣相沉積。在一實施例中,基板8係經本發明之新穎組合物之第一薄膜(新穎高碳底層,6)塗佈及含矽之另一抗反射塗層之第二塗層(矽底抗反射塗層,4)係經塗佈於該第一薄膜上。第二塗層可具有約0.05至0.5範圍內之吸收(k)值。隨後將光阻劑2之薄膜塗佈於第二塗層上。成像製程係如圖1所例示。
將光阻劑薄膜塗佈於抗反射塗層最上層之上並經烘烤以大體上移除光阻劑溶劑。在塗佈步驟之後可施加邊緣珠粒移除劑,以使用技藝中熟知方法清潔基板之邊緣。
基板(抗反射塗層係形成於其上)可為彼等通常用於半導體工業中之任意者。適宜的基板包括(但不限於)低介電常數材料、矽、經金屬表面塗佈之矽基板、經銅塗佈之矽晶圓、銅、鋁、聚合物樹脂、二氧化矽、金屬、經摻雜之二氧化矽、氮化矽、鉭、多晶矽、陶瓷、鋁/銅混合物;砷化鎵及其他此等第III/V族化合物。該基板可包括自上述材料所製造之任何數量的層。
光阻劑可為用於半導體工業中之任何類型,只要光阻劑中光活性化合物及抗反射塗層在用於成像製程之暴露波長處大體上吸收即可。
迄今為止,有若干在小型化中提供明顯進展及248 nm、193 nm、157 nm及13.5 nm之此等輻射之主要深紫外(uv)暴露技術。用於248 nm之光阻劑通常係基於經取代之多羥基苯乙烯及其共聚物/鎓鹽,諸如彼等US 4,491,628及US 5,350,660中所述者。另一方面,用於暴露在193 nm及157 nm處之光阻劑需要非芳族聚合物,因為芳族化合物在此波長處係不透明的。US 5,843,624及US 6,866,984揭示用於193 nm暴露之光阻劑。一般而言,包含脂環烴之聚合物係用於暴露在200 nm以下之光阻劑。由於許多原因,應將脂環烴併入該聚合物中,主要係因為其等具有可改善耐蝕刻性之相對高的碳對氫比率,其亦可在低波長處提供透明性及其等具有相對高的玻璃轉變溫度。US 5,843,624揭示用於光阻劑之聚合物,其係藉由馬來酸酐與不飽和環狀單體之自由基聚合作用獲得。可使用任何已知類型的193 nm光阻劑,諸如彼等US 6,447,980及US 6,723,488中所述者,及其等係以引用的方式併入本文中。已知在157 nm處敏感且係基於含側鏈氟醇基團之氟化聚合物的兩種基本類型之光阻劑在該波長處大體上係透明的。一類157 nm氟醇光阻劑係衍生自包含諸如氟化降冰片烯之基團之聚合物及係使用金屬催化或自由基聚合作用與其他透明單體(諸如四氟乙烯(US 6,790,587及US 6,849,377))均聚合或共聚合。一般而言,此等材料可提供更高的吸收率,但因其高脂環族含量而具有良好的耐電漿蝕刻性。最近,有闡述一類157 nm氟醇聚合物,其中該聚合物主鏈係衍生自不對稱二烯(諸如1,1,2,3,3-五氟-4-三氟甲基-4-羥基-1,6-庚二烯)之環聚合作用(US 6,818,258)或氟二烯與烯烴之共聚合作用(US 6,916,590)。此等材料在157 nm處提供可接受的吸收性,但因其脂環族含量比氟-降冰片烯聚合物低而具有較低的耐電漿蝕刻性。通常可混合此等兩類聚合物以在第一聚合物類型之高耐蝕刻性與第二聚合物類型之157 nm處高透明性之間提供平衡。吸收13.5 nm之極紫外輻射(EUV)之光阻劑亦有用及係技術中已知的。該新穎塗層亦可用於奈米印模及電子束微影術中。
在塗佈製程之後,將光阻劑以遮罩成像暴露。該暴露可利用典型的暴露設備完成。暴露波長源之實例係248 nm及193 nm,但可使用任何來源。隨後將經暴露之光阻劑於水性顯影劑中顯影以移除經處理之光阻劑。該顯影劑較佳為水性鹼性溶液,其包括(例如)四甲基氫氧化銨(TMAH)。顯影劑之實例係0.26N水性四甲基氫氧化銨(TMAH)溶液。該顯影劑可進一步包括界面活性劑。可視需要在顯影之前及暴露之後將加熱步驟併入該製程中。
將光阻劑塗佈及成像之製程係熟悉此項技術者熟知及係對於所用特定類型的光阻劑最佳。隨後可在適宜的蝕刻室中將圖案化基板以剩餘的光阻劑充當蝕刻遮罩用蝕刻氣體或氣體之混合物乾式蝕刻,以移除該抗反射薄膜或多層之抗反射塗層之暴露部份。各種蝕刻氣體係技藝中已知用於蝕刻有機抗反射塗層,諸如彼等包括O2
、CF4
、CHF3
、Cl2
、HBr、SO2
、CO等者。
以上各參考文獻之全文係針對所有目的以引用的方式併入本文中。以下特定實例可提供製造及利用本發明組合物之方法的詳細闡述。然而,此等實例並不以任何方式限制或限定本發明之範疇且不應視為提供唯一必需利用之條件、參數或值來實行本發明。
以下實例中之碳硬遮罩抗反射塗層之折射率(n)及吸收率(k)值係於J. A. Woollam VASE32橢圓偏光計上測量。
聚合物之莫耳重量係於凝膠滲透層析儀上測量。
將9-蒽甲醇(52.06 g~0.25莫耳)、二乙烯苯(16.3 g~0.125莫耳)置於裝備有攪拌器、冷凝器、熱力表及氮氣清掃之2升四頸圓底燒瓶中。添加213 g二(乙二醇)二甲基醚(二乙二醇二甲醚)及60 g環戊基甲基醚(CPME)及使其在氮氣下混合10分鐘。添加2.05 g三氟甲磺酸並使其混合10分鐘。將燒瓶加熱至140℃並回流三小時。在反應之後,將燒瓶冷卻並添加500 ml CPME。將反應混合物轉移至具有底部出口閥之5 L燒瓶中。添加300 mL去離子(DI)水,使其混合及靜置以形成分離水層。使聚合物溶液與5 L己烷混合。將沉澱物濾出,用己烷沖洗及在真空下乾燥。將粗聚合物(46.0 g)溶於四氫呋喃(THF)(400 ml)中。將該溶液添加至4升己烷中並形成沉澱物。將該聚合物之沉澱物過濾並用己烷沖洗,及在真空下乾燥以獲得54%的產率、1898的GPC Mw及1.77的多分散性(Pd)。所獲得之聚合物根據元素分析具有碳-92.29重量%,氫-5.91重量%,氧-1.8重量%。
將來自實例1之7.0 g聚合物、0.70 g四甲氧基甲基-雙酚(TMOM-BP)、2.80 g三乙胺與十二烷基苯磺酸作為鹽之含於環己酮/PGMEA(70/30)中之10%溶液及89.5 g環己酮/PGMEA(70/30)混合。在完成混合之後,將調配物經由0.04 μm過濾器過濾。
將來自實例2之經過濾溶液以1500 rpm旋塗於8"矽晶圓上。將經塗佈之晶圓於230℃加熱板上烘烤60秒。將經塗佈之薄材料藉由刀片自晶圓表面刮掉並完成元素分析。結果顯示於表1中。將另一矽晶圓用來自實例2之經過濾溶液以1500 rpm旋塗及將經塗佈之晶圓在400℃下烘烤120秒。將經烘烤之材料藉由刀片自晶圓表面刮掉並完成元素分析。結果顯示於表1中。
比較例1:
用二羥基甲基苯替代二乙烯苯來重複進行實例2。所獲得之聚合物提供60%產率、1374的GPC Mw及1.79的Pd,元素分析:碳-90.60重量%,氫-5.15重量%,氧-2.53重量%。
比較例2:
用來自比較例1之聚合物重複進行實例2。
比較例3:
用來自比較例2之材料重複進行實例3及結果顯示於以下表2中。
比較組合物2在加熱至400℃之後可得到比實例2之組合物更低的含碳量,其中希望在烘烤之後得到更高的含碳量,尤其係大於80重量%。
比較例4:
用二甲氧基甲基苯替代二乙烯苯來重複進行實例1。
所獲得之聚合物可提供1374的Mw、1.79的Pd。該聚合物自元素分析可得出碳-90.60重量%,氫-5.15重量%,及氧-4.25重量%。
比較例5:
用來自比較例4之聚合物重複進行比較例2。
比較例6:用來自比較例5之溶液重複進行比較例3,及結果顯示於以下表3中。
比較組合物5在加熱至400℃之後得到比實例2組合物更低的含碳量,其中希望在烘烤之後得到更高的含碳量。
n及k測量:將來自實例2之調配物用環己酮調節至1.25重量%固體,及將該混合物混合直至所有的材料變得可溶解為止。將均質溶液經由0.2 μm薄膜過濾器過濾。將此經過濾之溶液以2000 rpm旋塗於4"矽晶圓上。將經塗佈之晶圓於230℃加熱板上烘烤60秒。隨後,用由J. A. Woollam Co. Inc.製造之VASE橢圓偏光計測量n及k值。薄膜之光學常數n及k在193 nm輻射時係n=1.47,k=0.56。
將來自實例2之均質溶液用0.2 μm薄膜過濾器過濾。將此經過濾之溶液以1500 rpm旋塗於6"矽晶圓上。將經塗佈之晶圓在230℃加熱板上烘烤60秒。在烘烤之後,將晶圓冷卻至室溫且部份浸入PGME中30秒。該塗層係無缺陷的。檢測晶圓之浸入及未浸入區域的薄膜厚度變化。由於經烘烤薄膜之有效交聯,故在浸入區域中未觀察到薄膜損耗。
來自實例1之聚合物之等溫熱重量分析TGA係使用Perkin Elmer TGA 7在空氣中、400℃下測量120分鐘,及結果顯示該聚合物之重量損失係2.27%,因此表明該新穎聚合物具有極低的重量損失。
抗反射塗層之總蝕刻速率係使用表4中所概述之氧化(富含氧)及富含氟碳之蝕刻條件於NE-5000 N(ULVAC)上測量。將來自實例2及比較例2之具有約250 nm厚度的調配物之抗反射塗層薄膜分別塗佈於8"矽晶圓上及在230℃下烘烤1分鐘。在蝕刻20秒之前及之後使用得自薄膜之VASE分析及5點檢查之Cauchy's材料依賴性常數於Nanospec 8000上進行個別之薄膜厚度測量程序。繼而藉由將薄膜厚度差除以蝕刻時間來計算蝕刻速率。蝕刻速率遮罩能力係顯示於表5及表6之蝕刻速率數據中。比較例2提供比實例2更高的蝕刻速率,其中希望蝕刻速率更低。
板溫度:20℃;RF功率:500 W,50 W偏壓。
將8英吋晶圓用來自實例2之組合物以1500 rpm塗佈,從而得到200 nm薄膜厚度並在350℃下烘烤120秒。將含矽之底部抗反射塗層AZEXP ArF S24H(購自AZElectronic Materials USA Corps,Somerville,NJ之矽抗反射塗層)塗佈於其上,以得到31 nm薄膜厚度並在230℃下烘烤60秒。隨後將AZArF2110P光阻劑(購自AZElectronic Materials USA Corps,Somerville,NJ之193 nm光阻劑)塗佈於抗反射塗層上,以得到125 nm薄膜厚度並將其在100℃下軟烘烤60秒。使用193 nm暴露工具(Nikon NSR-306D:NA=0.85,偶極0.82/0.43)將光阻劑暴露成像,將其在110℃下烘烤60秒,隨後於0.26 N水性四甲基氫氧化銨(TMAH)溶液中顯影。隨後經掃描電子顯微鏡觀察到線及空間圖案並分析具有臨界尺寸50 nm、1:2間距之圖案。該光阻劑具有48.0 mJ/cm2
的光敏度。該光阻劑圖案具有良好的圖案輪廓,其在光阻劑圖案之底部無基腳或浮渣。該光阻劑圖案未顯示自基板至圖案中最低反射率之駐波。該光阻劑圖案可使用先前所述之蝕刻條件或其他最佳條件轉移至基板。將圖案樣本使用CF4
氣體蝕刻,其後使用O2
移除所有剩餘的有機材料。隨後將基板用CF4
氣體蝕刻。藉由掃描電子顯微鏡(SEM)觀察圖案之橫截面。
將9-蒽甲醇(166.6 g~0.80莫耳)、二乙烯苯(16.3 g~0.125莫耳)添加至裝備有攪拌器、冷凝器、熱力表及氮氣清掃之2升四頸圓底燒瓶中。添加500 g二(乙二醇)二甲基醚(二乙二醇二甲醚)及150 g環戊基甲基醚及使其在氮氣下混合10分鐘。添加6.5 g三氟甲磺酸並使其混合10分鐘。將燒瓶加熱至140℃並回流三小時。在反應之後,將燒瓶冷卻並添加500 ml CPME。添加400 mL去離子(DI)水,使其混合及靜置以形成分離水層。移除水層。使聚合物溶液與8 L己烷混合。將沉澱物濾出,用己烷沖洗及在真空下乾燥。將粗聚合物(154 g)溶於四氫呋喃(1386 g)中。將824 g己烷邊攪拌地慢慢添加至溶液中並形成沉澱物。將沉澱物過濾及用己烷沖洗,並在真空下乾燥以獲得經分餾聚合物之38%的產率、2162的GPC Mw及1.83的多分散性(Pd)。
用來自實例13之聚合物重複進行實例2。
用來自實例14之組合物重複進行實例3及結果顯示於表8中。
將9-蒽甲醇(26 g~0.125莫耳)、二乙烯苯(16.25 g~0.125莫耳)、及1-萘酚(18 g,0.125莫耳)添加至裝備有攪拌器、冷凝器、熱力表及氮氣清掃之2升四頸圓底燒瓶中。添加210 g二乙二醇二甲醚及60 g環戊基甲基醚,在氮氣下混合10分鐘。添加1.81 g三氟甲磺酸並使其混合10分鐘。將燒瓶加熱至140℃及回流三小時。在反應之後,將燒瓶冷卻至約80℃並添加500 ml CPME及1.3 g三乙胺。將反應混合物轉移至具有底部出口閥之5 L燒瓶中。添加300 mL DI水,使其混合及靜置,並形成分離水層。將該聚合物溶液添加至3 L己烷中。將聚合物沉澱物濾出,用己烷沖洗及在真空下乾燥。將聚合物(70.0 g)溶於THF(200 ml)中。將溶液添加至3.0升之第三丁基甲基醚中並形成沉澱。將該沉澱物過濾及用己烷沖洗,並在真空下乾燥。該聚合物產率為33%,GPC Mw為5561及Pd為2.04,元素分析:碳-87.11重量%,氫-5.95重量%,氧-6.95重量%。
將來自實例13之7.35 g經分餾聚合物添加至瓶中,添加來自實例16之1.84 g聚合物,添加0.37 g TMOM-BP,添加含於環己酮/PGMEA(70/30)中之2.94 g DBSA 10%溶液,添加含於70/30環己酮/PGMEA中為1%之0.50 g FC-4430(購自3M Company,MN)及86.9 g環己酮/PGMEA(70/30)。在混合之後,將調配物經由0.04 μm過濾器過濾。將經過濾之溶液以1500 rpm旋塗於8"矽晶圓上。將經塗佈之晶圓於230℃加熱板上烘烤60秒並檢查缺陷。該塗層完全無缺陷。
比較例18:
在無來自實例17的聚合物下重複進行實例17並在檢查之後發現該塗層具有塗層缺陷。
2...光阻劑
4...矽底抗反射塗層
6...新穎高碳底層
8...基板
圖1闡述一種三層之成像方法。
2...光阻劑
4...矽底抗反射塗層
6...新穎高碳底層
8...基板
Claims (17)
- 一種抗反射塗層組合物,其包括交聯劑及能夠藉由該交聯劑交聯之可交聯聚合物,其中該可交聯聚合物包括由結構(1)表示之單元:
- 如請求項1之組合物,其中該組合物中之該聚合物不含脂族多環基團。
- 如請求項1之組合物,其中R1 係甲基及R2 係甲基。
- 如請求項1之組合物,其中該稠合芳族環具有3或4個芳族環。
- 如請求項1之組合物,其中該酸產生劑係熱酸產生劑。
- 如請求項1之組合物,其中該聚合物具有1,200至10,000 的重量平均分子量。
- 如請求項1之組合物,其進一步包括界面活性劑。
- 如請求項1之組合物,其進一步包括第二聚合物,其中該第二聚合物包括羥基芳族基團。
- 如請求項1之組合物,其進一步包括第二聚合物,其中該第二聚合物包括羥基芳族基團且不含脂族多環。
- 如請求項1之組合物,其具有大於80重量%的固體含量之含碳量。
- 如請求項1之組合物,其中結構1中之A係選自由以下所組成之群:
- 一種製造微電子裝置之方法,其包括:a)對基板提供來自請求項1之抗反射塗層組合物之第一層;b)視需要在該第一抗反射塗層組合物層上提供至少一層第二抗反射塗層;c)將光阻劑層塗佈至該抗反射塗層上;d)將該光阻劑層成像暴露;e)用水性鹼性顯影溶液將該光阻劑層顯影。
- 如請求項12之方法,其中該第一抗反射塗層組合物層具 有介於約0.05至約1.0範圍內之得自橢圓偏光測量之吸收參數(k)值。
- 如請求項12之方法,其中該第二抗反射塗層包含矽。
- 如請求項12之方法,其中該第二抗反射塗層具有介於約0.05至約0.5範圍內之得自橢圓偏光測量之吸收參數(k)值。
- 如請求項12之方法,其中該光阻劑層可用約240nm至約12nm之輻射成像。
- 如請求項12之方法,其中該顯影溶液係一種包含氫氧化物鹼之水溶液。
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Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
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US8017296B2 (en) | 2007-05-22 | 2011-09-13 | Az Electronic Materials Usa Corp. | Antireflective coating composition comprising fused aromatic rings |
US20100119979A1 (en) * | 2008-11-13 | 2010-05-13 | Rahman M Dalil | Antireflective Coating Composition Comprising Fused Aromatic Rings |
US20100119980A1 (en) * | 2008-11-13 | 2010-05-13 | Rahman M Dalil | Antireflective Coating Composition Comprising Fused Aromatic Rings |
US20100316949A1 (en) * | 2009-06-10 | 2010-12-16 | Rahman M Dalil | Spin On Organic Antireflective Coating Composition Comprising Polymer with Fused Aromatic Rings |
KR101411737B1 (ko) * | 2009-09-29 | 2014-06-25 | 제이에스알 가부시끼가이샤 | 패턴 형성 방법 및 레지스트 하층막 형성용 조성물 |
KR101432605B1 (ko) * | 2010-12-16 | 2014-08-21 | 제일모직주식회사 | 하드마스크 조성물, 이를 사용한 패턴 형성 방법 및 상기 패턴을 포함하는 반도체 집적회로 디바이스 |
US8906590B2 (en) * | 2011-03-30 | 2014-12-09 | Az Electronic Materials Usa Corp. | Antireflective coating composition and process thereof |
KR101413069B1 (ko) | 2011-12-30 | 2014-07-02 | 제일모직 주식회사 | 하드마스크 조성물용 모노머, 상기 모노머를 포함하는 하드마스크 조성물 및 상기 하드마스크 조성물을 사용하는 패턴형성방법 |
US8906592B2 (en) | 2012-08-01 | 2014-12-09 | Az Electronic Materials (Luxembourg) S.A.R.L. | Antireflective coating composition and process thereof |
KR101599961B1 (ko) | 2012-12-26 | 2016-03-04 | 제일모직 주식회사 | 모노머, 상기 모노머를 포함하는 하드마스크 조성물 및 상기 하드마스크 조성물을 사용하는 패턴형성방법 |
US9152051B2 (en) | 2013-06-13 | 2015-10-06 | Az Electronics Materials (Luxembourg) S.A.R.L. | Antireflective coating composition and process thereof |
TWI541611B (zh) | 2013-06-26 | 2016-07-11 | 第一毛織股份有限公司 | 用於硬罩幕組合物的單體、包括該單體的硬罩幕組合物及使用該硬罩幕組合物形成圖案的方法 |
KR20160029308A (ko) | 2014-09-05 | 2016-03-15 | 전남대학교산학협력단 | 염증질환 또는 면역질환 치료제로서의 식물유래 GA733-2-Fc 단백질 및 이의 제조방법 |
US9908990B2 (en) * | 2015-04-17 | 2018-03-06 | Samsung Sdi Co., Ltd. | Organic layer composition, organic layer, and method of forming patterns |
US11500291B2 (en) * | 2017-10-31 | 2022-11-15 | Rohm And Haas Electronic Materials Korea Ltd. | Underlying coating compositions for use with photoresists |
US11069570B2 (en) * | 2018-10-31 | 2021-07-20 | Taiwan Semiconductor Manufacturing Co., Ltd. | Method for forming an interconnect structure |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08301980A (ja) * | 1995-05-01 | 1996-11-19 | Nippon Steel Chem Co Ltd | 新規エポキシ樹脂、中間体及び製造法、並びにこれを用いたエポキシ樹脂組成物及びその硬化物 |
TW200801818A (en) * | 2006-03-14 | 2008-01-01 | Jsr Corp | Composition for forming under film and method for forming pattern |
JP2009014816A (ja) * | 2007-07-02 | 2009-01-22 | Jsr Corp | レジスト下層膜形成用組成物及びパターン形成方法 |
Family Cites Families (92)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US316949A (en) * | 1885-05-05 | Potato-digger | ||
US3474058A (en) * | 1966-01-19 | 1969-10-21 | Nat Distillers Chem Corp | Compositions comprising ethylene-vinyl acetate copolymer,fatty acid salt and fatty acid amide |
US3474054A (en) * | 1966-09-13 | 1969-10-21 | Permalac Corp The | Surface coating compositions containing pyridine salts or aromatic sulfonic acids |
US4200729A (en) * | 1978-05-22 | 1980-04-29 | King Industries, Inc | Curing amino resins with aromatic sulfonic acid oxa-azacyclopentane adducts |
US4251665A (en) * | 1978-05-22 | 1981-02-17 | King Industries, Inc. | Aromatic sulfonic acid oxa-azacyclopentane adducts |
US4463162A (en) * | 1980-12-09 | 1984-07-31 | Asahi-Dow Limited | Polynuclear fused aromatic ring type polymer and preparation thereof |
US4491628A (en) * | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
US4758653A (en) * | 1985-02-18 | 1988-07-19 | Fuji Standard Research Inc. | Thermosetting composition, method of producing fusible thermosetting resin using same, and process for the production of condensed, polynuclear aromatic hydrocarbon resin using same |
JPH0618861B2 (ja) | 1986-03-31 | 1994-03-16 | 住金化工株式会社 | 熱硬化性樹脂組成物 |
US4719166A (en) * | 1986-07-29 | 1988-01-12 | Eastman Kodak Company | Positive-working photoresist elements containing anti-reflective butadienyl dyes which are thermally stable at temperatures of at least 200° C. |
JPS6351419A (ja) | 1986-08-21 | 1988-03-04 | Sugiro Otani | 熱硬化性炭化水素樹脂の製造方法 |
EP0440374B1 (en) * | 1990-01-30 | 1997-04-16 | Wako Pure Chemical Industries Ltd | Chemical amplified resist material |
US5187019A (en) * | 1991-09-06 | 1993-02-16 | King Industries, Inc. | Latent catalysts |
US5294680A (en) | 1992-07-24 | 1994-03-15 | International Business Machines Corporation | Polymeric dyes for antireflective coatings |
US5607824A (en) * | 1994-07-27 | 1997-03-04 | International Business Machines Corporation | Antireflective coating for microlithography |
JPH0873570A (ja) | 1994-09-12 | 1996-03-19 | Dainippon Ink & Chem Inc | フェノールアラルキル型樹脂の製造方法および硬化性エポキシ樹脂組成物 |
US5747599A (en) | 1994-12-12 | 1998-05-05 | Kansai Paint Company, Limited | Thermosetting coating composition |
BR9610547A (pt) * | 1995-09-12 | 1999-07-06 | Dow Chemical Co | Compostos aromáticos substituídos com etinila síntese polímeros e usos dos mesmos |
US5843624A (en) * | 1996-03-08 | 1998-12-01 | Lucent Technologies Inc. | Energy-sensitive resist material and a process for device fabrication using an energy-sensitive resist material |
WO1997048749A1 (fr) | 1996-06-17 | 1997-12-24 | Daicel Chemical Industries, Ltd. | Polyene epoxyde, composition de resine epoxy et produit resultant de son durcissement, et materiau de revetement pulverulent |
US5688598A (en) * | 1996-06-28 | 1997-11-18 | Morton International, Inc. | Non-blistering thick film coating compositions and method for providing non-blistering thick film coatings on metal surfaces |
US5965679A (en) * | 1996-09-10 | 1999-10-12 | The Dow Chemical Company | Polyphenylene oligomers and polymers |
US6228552B1 (en) * | 1996-09-13 | 2001-05-08 | Kabushiki Kaisha Toshiba | Photo-sensitive material, method of forming a resist pattern and manufacturing an electronic parts using photo-sensitive material |
DE69707635T2 (de) * | 1996-12-24 | 2002-08-08 | Fuji Photo Film Co Ltd | Zusammensetzung für Antireflexunterschichten und Verfahren zur Herstellung eines Resistmusters damit |
US6808859B1 (en) * | 1996-12-31 | 2004-10-26 | Hyundai Electronics Industries Co., Ltd. | ArF photoresist copolymers |
TW473475B (en) | 1997-03-04 | 2002-01-21 | Kyowa Yuka Kk | Diglycidyl ether, composition containing thereof, curing process of epoxy resin and cured product |
JP4110589B2 (ja) | 1997-03-31 | 2008-07-02 | 日立化成工業株式会社 | 回路用接続部材及び回路板の製造法 |
US5981145A (en) | 1997-04-30 | 1999-11-09 | Clariant Finance (Bvi) Limited | Light absorbing polymers |
TW473653B (en) * | 1997-05-27 | 2002-01-21 | Clariant Japan Kk | Composition for anti-reflective film or photo absorption film and compound used therein |
US6468718B1 (en) * | 1999-02-04 | 2002-10-22 | Clariant Finance (Bvi) Limited | Radiation absorbing polymer, composition for radiation absorbing coating, radiation absorbing coating and application thereof as anti-reflective coating |
US5935760A (en) | 1997-10-20 | 1999-08-10 | Brewer Science Inc. | Thermosetting polyester anti-reflective coatings for multilayer photoresist processes |
CA2243727A1 (en) | 1998-01-30 | 1999-07-30 | James J. Briguglio | Positive-tone photoimageable crosslinkable coating |
JPH11249311A (ja) | 1998-03-03 | 1999-09-17 | Jsr Corp | 反射防止膜形成用組成物 |
US20010006759A1 (en) * | 1998-09-08 | 2001-07-05 | Charles R. Shipley Jr. | Radiation sensitive compositions |
JP3542931B2 (ja) | 1998-09-08 | 2004-07-14 | 雅夫 鬼澤 | イソプレン・イソブチレンゴムの架橋方法およびその方法によって架橋して得られるゴム製品 |
US6849377B2 (en) * | 1998-09-23 | 2005-02-01 | E. I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
US6316165B1 (en) * | 1999-03-08 | 2001-11-13 | Shipley Company, L.L.C. | Planarizing antireflective coating compositions |
US6323287B1 (en) * | 1999-03-12 | 2001-11-27 | Arch Specialty Chemicals, Inc. | Hydroxy-amino thermally cured undercoat for 193 NM lithography |
US6790587B1 (en) * | 1999-05-04 | 2004-09-14 | E. I. Du Pont De Nemours And Company | Fluorinated polymers, photoresists and processes for microlithography |
US6440642B1 (en) | 1999-09-15 | 2002-08-27 | Shipley Company, L.L.C. | Dielectric composition |
US6268072B1 (en) * | 1999-10-01 | 2001-07-31 | Eastman Kodak Company | Electroluminescent devices having phenylanthracene-based polymers |
WO2001040865A1 (en) * | 1999-11-30 | 2001-06-07 | Brewer Science, Inc. | Non-aromatic chromophores for use in polymer anti-reflective coatings |
EP1302813A4 (en) * | 2000-06-21 | 2005-02-23 | Asahi Glass Co Ltd | RESIST COMPOSITION |
JP3971088B2 (ja) | 2000-06-30 | 2007-09-05 | 株式会社東芝 | パターン形成方法 |
US6447980B1 (en) * | 2000-07-19 | 2002-09-10 | Clariant Finance (Bvi) Limited | Photoresist composition for deep UV and process thereof |
TW583503B (en) * | 2000-12-01 | 2004-04-11 | Kansai Paint Co Ltd | Method of forming conductive pattern |
WO2002065212A1 (fr) * | 2001-02-09 | 2002-08-22 | Asahi Glass Company, Limited | Composition de reserve |
US6410208B1 (en) * | 2001-04-18 | 2002-06-25 | Gary Ganghui Teng | Lithographic printing plates having a thermo-deactivatable photosensitive layer |
TW576859B (en) * | 2001-05-11 | 2004-02-21 | Shipley Co Llc | Antireflective coating compositions |
JP2003082070A (ja) | 2001-09-07 | 2003-03-19 | Sumitomo Metal Ind Ltd | 縮合多環芳香族樹脂とその製造方法 |
TW591341B (en) * | 2001-09-26 | 2004-06-11 | Shipley Co Llc | Coating compositions for use with an overcoated photoresist |
US6723488B2 (en) * | 2001-11-07 | 2004-04-20 | Clariant Finance (Bvi) Ltd | Photoresist composition for deep UV radiation containing an additive |
CN1606713B (zh) * | 2001-11-15 | 2011-07-06 | 霍尼韦尔国际公司 | 用于照相平版印刷术的旋涂抗反射涂料 |
US6730454B2 (en) * | 2002-04-16 | 2004-05-04 | International Business Machines Corporation | Antireflective SiO-containing compositions for hardmask layer |
US7264913B2 (en) * | 2002-11-21 | 2007-09-04 | Az Electronic Materials Usa Corp. | Antireflective compositions for photoresists |
JP4013058B2 (ja) | 2002-12-24 | 2007-11-28 | 信越化学工業株式会社 | パターン形成方法及び下層膜形成材料 |
JP4069025B2 (ja) | 2003-06-18 | 2008-03-26 | 信越化学工業株式会社 | レジスト下層膜材料ならびにパターン形成方法 |
GB2404284B (en) * | 2003-07-10 | 2007-02-21 | Dainippon Printing Co Ltd | Organic electroluminescent element |
JP4206851B2 (ja) | 2003-07-23 | 2009-01-14 | Jsr株式会社 | 反射防止膜形成組成物及び反射防止膜の形成方法 |
JP4235698B2 (ja) * | 2003-08-21 | 2009-03-11 | 旭化成ケミカルズ株式会社 | 感光性組成物およびその硬化物 |
US7303855B2 (en) * | 2003-10-03 | 2007-12-04 | Shin-Etsu Chemical Co., Ltd. | Photoresist undercoat-forming material and patterning process |
TWI274771B (en) | 2003-11-05 | 2007-03-01 | Mitsui Chemicals Inc | Resin composition, prepreg and laminate using the same |
US6899963B1 (en) * | 2004-02-25 | 2005-05-31 | Eastman Kodak Company | Electroluminescent devices having pendant naphthylanthracene-based polymers |
US20050186444A1 (en) * | 2004-02-25 | 2005-08-25 | Eastman Kodak Company | Electroluminescent devices having conjugated arylamine polymers |
US7427464B2 (en) * | 2004-06-22 | 2008-09-23 | Shin-Etsu Chemical Co., Ltd. | Patterning process and undercoat-forming material |
KR100757861B1 (ko) * | 2004-07-21 | 2007-09-11 | 삼성전자주식회사 | 잉크젯 헤드 기판, 잉크젯 헤드 및 잉크젯 헤드 기판의제조방법. |
EP1785441B1 (en) * | 2004-09-01 | 2011-06-08 | DIC Corporation | Epoxy resin composition, products of curing thereof, material for the encapsulation of semiconductors, novel phenol resin, novel epoxy resin, process for production of novel phenol resin and process for production of novel epoxy resin |
EP1691238A3 (en) * | 2005-02-05 | 2009-01-21 | Rohm and Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
US7816071B2 (en) * | 2005-02-10 | 2010-10-19 | Az Electronic Materials Usa Corp. | Process of imaging a photoresist with multiple antireflective coatings |
TWI338816B (en) * | 2005-03-11 | 2011-03-11 | Shinetsu Chemical Co | Photoresist undercoat-forming material and patterning process |
EP1705519B1 (en) | 2005-03-20 | 2016-07-06 | Rohm and Haas Electronic Materials, L.L.C. | Method of treating a microelectronic substrate |
JP4575220B2 (ja) * | 2005-04-14 | 2010-11-04 | 信越化学工業株式会社 | レジスト下層膜材料およびパターン形成方法 |
EP1762895B1 (en) * | 2005-08-29 | 2016-02-24 | Rohm and Haas Electronic Materials, L.L.C. | Antireflective Hard Mask Compositions |
JP4666166B2 (ja) * | 2005-11-28 | 2011-04-06 | 信越化学工業株式会社 | レジスト下層膜材料及びパターン形成方法 |
EP1829942B1 (en) | 2006-02-28 | 2012-09-26 | Rohm and Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
JP5112733B2 (ja) | 2006-04-11 | 2013-01-09 | ローム・アンド・ハース・エレクトロニック・マテリアルズ,エル.エル.シー. | フォトリソグラフィ用コーティング組成物 |
CN100425630C (zh) | 2006-04-19 | 2008-10-15 | 苏州市成技新材料开发有限公司 | 含硅偶联剂共聚物成膜树脂及其有机防反射涂膜 |
JP5362176B2 (ja) * | 2006-06-12 | 2013-12-11 | ルネサスエレクトロニクス株式会社 | 半導体装置の製造方法 |
JP4727567B2 (ja) | 2006-12-27 | 2011-07-20 | Azエレクトロニックマテリアルズ株式会社 | 反射防止膜形成用組成物およびそれを用いたパターン形成方法 |
KR100896451B1 (ko) * | 2006-12-30 | 2009-05-14 | 제일모직주식회사 | 카본 함량이 개선된 고 내에칭성 반사방지 하드마스크조성물, 이를 이용한 패턴화된 재료 형상의 제조방법 |
CN101641390B (zh) | 2007-04-02 | 2013-05-01 | 第一毛织株式会社 | 具有抗反射性能的硬掩模组合物及用其图案化材料的方法 |
US8017296B2 (en) * | 2007-05-22 | 2011-09-13 | Az Electronic Materials Usa Corp. | Antireflective coating composition comprising fused aromatic rings |
US20080292987A1 (en) * | 2007-05-22 | 2008-11-27 | Francis Houlihan | Antireflective Coating Composition Comprising Fused Aromatic Rings |
KR100908601B1 (ko) * | 2007-06-05 | 2009-07-21 | 제일모직주식회사 | 반사방지 하드마스크 조성물 및 이를 이용한 기판상 재료의패턴화 방법 |
JP4993139B2 (ja) * | 2007-09-28 | 2012-08-08 | 信越化学工業株式会社 | 反射防止膜形成材料、反射防止膜及びこれを用いたパターン形成方法 |
KR100930673B1 (ko) * | 2007-12-24 | 2009-12-09 | 제일모직주식회사 | 반사방지 하드마스크 조성물 및 이를 이용한재료의 패턴화 방법 |
US7989144B2 (en) * | 2008-04-01 | 2011-08-02 | Az Electronic Materials Usa Corp | Antireflective coating composition |
US7932018B2 (en) * | 2008-05-06 | 2011-04-26 | Az Electronic Materials Usa Corp. | Antireflective coating composition |
US20100119980A1 (en) | 2008-11-13 | 2010-05-13 | Rahman M Dalil | Antireflective Coating Composition Comprising Fused Aromatic Rings |
US20100119979A1 (en) | 2008-11-13 | 2010-05-13 | Rahman M Dalil | Antireflective Coating Composition Comprising Fused Aromatic Rings |
US20100151392A1 (en) | 2008-12-11 | 2010-06-17 | Rahman M Dalil | Antireflective coating compositions |
US20100316949A1 (en) | 2009-06-10 | 2010-12-16 | Rahman M Dalil | Spin On Organic Antireflective Coating Composition Comprising Polymer with Fused Aromatic Rings |
-
2009
- 2009-12-23 US US12/646,191 patent/US8486609B2/en active Active
-
2010
- 2010-12-14 TW TW099143805A patent/TWI510862B/zh active
- 2010-12-23 EP EP10813006.3A patent/EP2516566B1/en active Active
- 2010-12-23 JP JP2012545468A patent/JP5822358B2/ja active Active
- 2010-12-23 KR KR1020127013194A patent/KR101833075B1/ko active IP Right Grant
- 2010-12-23 WO PCT/IB2010/003373 patent/WO2011077241A2/en active Application Filing
- 2010-12-23 CN CN201080054063.5A patent/CN102630246B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08301980A (ja) * | 1995-05-01 | 1996-11-19 | Nippon Steel Chem Co Ltd | 新規エポキシ樹脂、中間体及び製造法、並びにこれを用いたエポキシ樹脂組成物及びその硬化物 |
TW200801818A (en) * | 2006-03-14 | 2008-01-01 | Jsr Corp | Composition for forming under film and method for forming pattern |
JP2009014816A (ja) * | 2007-07-02 | 2009-01-22 | Jsr Corp | レジスト下層膜形成用組成物及びパターン形成方法 |
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EP2516566A2 (en) | 2012-10-31 |
US20110151376A1 (en) | 2011-06-23 |
WO2011077241A8 (en) | 2012-02-16 |
TW201140250A (en) | 2011-11-16 |
KR20120102646A (ko) | 2012-09-18 |
US8486609B2 (en) | 2013-07-16 |
CN102630246A (zh) | 2012-08-08 |
WO2011077241A2 (en) | 2011-06-30 |
WO2011077241A3 (en) | 2011-08-18 |
JP5822358B2 (ja) | 2015-11-24 |
JP2013515972A (ja) | 2013-05-09 |
KR101833075B1 (ko) | 2018-02-27 |
EP2516566B1 (en) | 2018-07-18 |
CN102630246B (zh) | 2016-05-11 |
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