TWI532785B - 硬罩幕組成物、形成圖案的方法以及半導體積體電路裝置 - Google Patents
硬罩幕組成物、形成圖案的方法以及半導體積體電路裝置 Download PDFInfo
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- TWI532785B TWI532785B TW103142270A TW103142270A TWI532785B TW I532785 B TWI532785 B TW I532785B TW 103142270 A TW103142270 A TW 103142270A TW 103142270 A TW103142270 A TW 103142270A TW I532785 B TWI532785 B TW I532785B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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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- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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- C—CHEMISTRY; METALLURGY
- 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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- G—PHYSICS
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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
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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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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- 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
- H01L21/02104—Forming layers
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Description
本申請案主張2013年12月31日在韓國智慧財產局提出的韓國專利申請案第10-2013-0169260號的優先權和權益,所述專利申請案的全部內容以引用的方式併入本文中。
公開一種硬罩幕組成物、一種使用所述硬罩幕組成物形成圖案的方法以及一種包含所述圖案的半導體積體電路裝置。
最近,半導體行業已發展到具有幾奈米到幾十奈米尺寸的圖案的超精細技術。這種超精細技術主要需要有效的光微影技術。典型的光微影技術包含:在半導體基底上提供材料層;在材料層上塗佈光阻層;曝光且顯影光阻層以提供光阻圖案;以及使用光阻圖案作為罩幕來蝕刻材料層。如今,由於待形成的圖案尺寸較小,僅僅通過上述典型的光微影技術難以得到具有極佳輪廓
的精細圖案。因此,可在材料層與光阻層之間形成被稱作硬罩幕層的層來得到精細圖案。硬罩幕層起到中間層的作用,用於通過選擇性蝕刻製程將光阻的精細圖案轉移到材料層。因此,需要硬罩幕層具有例如耐熱性和抗蝕刻性等特徵以使其在多種蝕刻製程期間耐受。另一方面,最近已提出通過以旋塗法代替化學氣相沉積來形成硬罩幕層。旋塗法易於執行並且還可改良間隙填充特徵和平坦化特徵。旋塗法可使用對於溶劑具有可溶性的硬罩幕組成物。然而,硬罩幕層所需的以上特徵與可溶性相抵觸,因此需要滿足這兩者的硬罩幕組成物。
一個實施例提供了在確保對於溶劑具有可溶性、間隙填充特徵以及平坦化特徵的同時滿足耐熱性和抗蝕刻性的一種硬罩幕組成物。
另一實施例提供了一種使用所述硬罩幕組成物形成圖案的方法。
另一實施例提供了一種包含通過所述方法形成的圖案的半導體積體電路裝置。
根據一個實施例,提供了一種硬罩幕組成物,其包含:聚合物,所述聚合物包含由以下化學式1a到化學式1c中的一者表示的部分;由以下化學式2表示的單體;以及溶劑。
[化學式1a]
在上述化學式1a、化學式1b、化學式1c和化學式2中,R1a和R1b獨立地為通過在選自以下族群1的一種化合物中取代兩個氫原子所形成的鍵聯基團;R4a和R4b獨立地為通過在選自以下族群1的一種化合物中取代一個氫原子所形成的取代基;R2a、R2b、R5a和R5b獨立地為選自氫、羥基、胺基、經取代或未經取代的C1到C10烷基、經取代或未經取代的C6到C10芳基、經取代或未經取代的C1到C10烯丙基和鹵素的一者;以及R3選自以下族群2。
在族群1中:M1和M2獨立地為氫、羥基、亞硫醯基、硫醇基、氰基、經取代或未經取代的氨基、鹵素、含鹵素的基團、經取代或未經取代的C1到C30烷氧基或其組合。
在族群1中,每個環的每個鍵聯位置是不受特定限制的。
聚合物可進一步包含由以下化學式3表示的部分。
[化學式3]
*-R6-R7-*
在上述化學式3中,R6為選自族群1的一者;以及R7為選自族群2的一者。
聚合物可具有約1,000到約200,000的重量平均分子量。
聚合物與單體的重量比可為聚合物:單體=約9:1到約1:9。
以100重量份溶劑計,聚合物和單體的量可占約5重量份到約100重量份。
溶劑可包含選自丙二醇單甲基醚乙酸酯(propylene glycol monomethyl ether acetate,PGMEA)、丙二醇單甲基醚(propylene glycol monomethylether,PGME)、環己酮和乳酸乙酯的至少一者。
硬罩幕組成物可進一步包含交聯劑。
根據另一實施例,形成圖案的方法包含:在基底上提供材料層;在材料層上塗覆硬罩幕組成物以形成硬罩幕層;熱處理硬罩幕組成物以形成硬罩幕層;在硬罩幕層上形成含矽薄層;在含矽薄層上形成光阻層;曝光且顯影光阻層以形成光阻圖案;使用光阻圖案選擇性地去除含矽薄層和硬罩幕層以暴露材料層的一部分;以及蝕刻材料層的暴露部分。
可使用旋塗法來塗覆硬罩幕組成物。
形成硬罩幕層的製程可包含約100℃到約500℃的熱處理。
所述方法可進一步包含在含矽薄層上形成底部抗反射塗
層(bottom antireflective coating,BARC)。
含矽薄層可包含氮氧化矽(silicon oxynitride,SiON)、氮化矽(silicon nitride,Si3N4)或其組合。
根據另一實施例,提供了包含多個通過所述形成圖案的方法所形成的圖案的半導體積體電路裝置。
可改良硬罩幕層所需的特徵,例如耐熱性、抗蝕刻性、平坦化特徵和間隙填充特徵。
h1、h2‧‧‧高度
圖1為表明平坦化特徵的高度h1與高度h2之間的差異的剖面圖。。
下文將詳細描述本發明的例示性實施例,且其可由具有相關技術常識的人員容易地執行。然而,本發明可用多種不同形式實施,且不應理解為受限於本文所闡述的例示性實施例。
未另外提供定義時,如本文所使用,術語‘經取代’可指經選自以下的取代基代替化合物的氫原子者:鹵素原子(F、Br、Cl或I)、羥基、烷氧基、硝基、氰基、氨基、疊氮基、甲脒基、肼基、亞肼基、羰基、氨甲醯基、硫醇基、酯基、羧基或其鹽、磺酸基或其鹽、磷酸基或其鹽、C1到C20烷基、C2到C20烯基、C2到C20炔基、C6到C30芳基、C7到C30芳烷基、經取代或未經取代的C1到C20烷基硼烷基、經取代或未經取代的C6到C30
芳基硼烷基、C1到C4烷氧基、C1到C20雜烷基、C3到C20雜芳基烷基、C3到C30環烷基、C3到C15環烯基、C6到C15環炔基、C2到C30雜環烷基以及其組合。
未另外提供定義時,如本文所使用,術語‘雜’是指包含1到3個選自B、N、O、S和P的雜原子者。
未另外提供定義時,如本文所使用,*可表示化合物中用以鍵連的點。
下文描述了根據一個實施例的硬罩幕組成物。
根據一個實施例的硬罩幕組成物包含:聚合物,所述聚合物包含由以下化學式1a到化學式1c中的一者表示的部分;由以下化學式2表示的單體;以及溶劑。
[化學式2]
在上述化學式1a、化學式1b、化學式1c和化學式2中,R1a和R1b獨立地為通過在選自以下族群1的一種化合物中取代兩個氫原子所形成的鍵聯基團;R4a和R4b獨立地為通過在選自以下族群1的一種化合物中取代一個氫原子所形成的取代基;R2a、R2b、R5a和R5b獨立地為選自氫(-H)、羥基(-OH)、胺基(-NH2)、經取代或未經取代的C1到C10烷基、經取代或未經取代的C6到C10芳基、經取代或未經取代的C1到C10烯丙基和鹵素的一者;以及R3選自以下族群2。
在族群1中,M1和M2獨立地為氫、羥基、亞硫醯基、硫醇基、氰基、經取代或未經取代的氨基、鹵素、含鹵素的基團、經
取代或未經取代的C1到C30烷氧基或其組合。
在族群1中,每個環的每個鍵聯位置是不受特定限制的。
由上述化學式1a到化學式1c中的一者表示的部分具有芳香環,且硬罩幕組成物包含具有所述部分的聚合物並且因此可確保剛性特徵。
硬罩幕組成物包含通過摻合包含由上述化學式1a到化學式1c中的一者表示的部分的聚合物與由上述化學式2表示的單體所獲得的化合物。因此,硬罩幕組成物可具有令人滿意的耐熱性與抗蝕刻性以及穩定的可溶性、間隙填充特徵和平坦化特徵。
由上述化學式1a到化學式1c中的一者表示的部分和由上述化學式2表示的單體均具有芴主鏈。換句話說,硬罩幕組成物包含通過摻合彼此具有類似結構的聚合物與單體所獲得的化合物。因此,所述化合物可減弱聚合物與單體之間的排斥力和差異感且幫助聚合物和單體很好地分散在組成物中,並且因此彌補每個部分的缺點且確保極佳的間隙填充特徵和平坦化特徵。此外,摻合以這種方式具有類似結構的聚合物和單體,且因此可將歸因
於聚合物和單體固有特徵的摻合材料的特徵變化降到最小。
在上述化學式1a到化學式1c以及化學式2中,R2a、R2b、R5a和R5b表示在芴主鏈中取代的取代基。取代基的位置和數目無限制,且可適當地調整取代基的位置和數目以控制特性。
如上所述,聚合物可包含多個由上述化學式1a到化學式1c中的一者表示的部分,所述多個部分可具有相同結構或不同結構。舉例來說,聚合物可包含由上述化學式1a和化學式1b表示的部分。舉例來說,聚合物可包含兩個不同的由上述化學式1a表示的部分。
聚合物可進一步包含由以下化學式3表示的部分。
[化學式3]*-R6-R7-*
在上述化學式3中:R6為選自族群1的一者;以及R7為選自族群2的一者。
當聚合物包含由上述化學式3表示的部分時,由上述化學式1a到化學式1c中的一者以及上述化學式3表示的部分在它們的排列順序和重量比方面無特定限制。
舉例來說,可按在所要的聚合物重量平均分子量範圍內的適當莫爾比來使用聚合物中由上述化學式1a到化學式1c中的一者表示的部分和由上述化學式3表示的部分。舉例來說,聚合物可具有約1,000到約200,000的重量平均分子量。
聚合物可包含多個由上述化學式3表示的部分,且所述部分可具有相同結構或不同結構。
另一方面,可例如以約9:1到約1:9且具體地說以約7:3到約3:7的重量比來使用聚合物和單體,但重量比不限於此。
硬罩幕組成物中的溶劑可為足夠溶解或分散單體和聚合物的任何物質,且可為例如選自丙二醇(propylene glycol)、丙二醇二乙酸酯(propylene glycol diacetate)、甲氧基丙二醇(methoxy propanediol)、二乙二醇(diethylene glycol)、二乙二醇丁基醚(diethylene glycol butylether)、三(乙二醇)單甲基醚(tri(ethylene glycol)monomethylether)、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、環己酮、乳酸乙酯、γ-丁內酯(gamma-butyrolactone)、甲基吡咯烷酮(methyl pyrrolidone)和乙醯丙酮(acetylacetone)的至少一者。
以100重量份所述溶劑計,聚合物和單體的量可占約5重量份到約100重量份。當包含在上述範圍內的聚合物和單體時,可獲得所要的經塗佈薄膜厚度。
硬罩幕組成物可進一步包含表面活性劑。
表面活性劑可包含例如烷基苯磺酸鹽(alkylbenzene sulfonate salt)、烷基吡啶鎓鹽(alkyl pyridinium salt)、聚乙二醇(polyethylene glycol)或季銨鹽(quaternary ammonium salt),但不限於此。
以100重量份硬罩幕組成物計,表面活性劑的量可占約0.001重量份到約3重量份。在所述量的範圍內,可確保硬罩幕組成物的溶解性同時不改變其光學特性。
硬罩幕組成物可進一步包含交聯劑。
交聯劑可包含選自氨基樹脂、甘脲(glycoluril)化合物、
雙環氧化合物、三聚氰胺化合物和三聚氰胺衍生物的至少一者。
以100重量份硬罩幕組成物計,交聯劑的量可占約0.001重量份到約3重量份。
下文描述了一種通過使用硬罩幕組成物來形成圖案的方法。
根據一個實施例,形成圖案的方法包含:在基底上提供材料層;在材料層上塗覆包含聚合物、單體和溶劑的硬罩幕組成物;熱處理硬罩幕組成物以形成硬罩幕層;在硬罩幕層上形成含矽薄層;在含矽薄層上形成光阻層;曝光且顯影光阻層以形成光阻圖案;使用光阻圖案選擇性地去除含矽薄層和硬罩幕層以暴露材料層的一部分;以及蝕刻材料層的暴露部分。
基底可為例如矽晶圓、玻璃基底或聚合物基底。
材料層為待最終圖案化的材料,例如比如鋁層和銅層等金屬層、例如矽層等半導體層或例如氧化矽層和氮化矽層等絕緣層。材料層可通過例如化學氣相沉積(chemical vapor deposition,CVD)製程等方法形成。
硬罩幕組成物可呈溶液的形式通過旋塗法塗覆。在這裡,硬罩幕組成物的厚度是不受特定限制的,但可為例如約100埃到約10,000埃。
可在例如約100℃到約500℃下對硬罩幕組成物進行熱處理,持續約10秒到10分鐘。在熱處理期間,化合物可引起自交聯和/或相互交聯反應。
含矽薄層可由例如氮化矽、氧化矽或氮氧化矽(SiON)構成。
所述方法可進一步包含在含矽薄層上形成底部抗反射塗層(BARC)。舉例來說,可在硬罩幕層上形成含氮氧化矽的薄層,接著形成底部抗反射塗層,且隨後在底部抗反射塗層上形成光阻層。
可使用例如ArF、KrF或遠紫外光(extreme ultraviolet,EUV)進行光阻層曝光。曝光後,可在約100℃到約500℃下進行熱處理。
可通過使用蝕刻氣體的乾式蝕刻製程對材料層暴露部分進行蝕刻製程,且蝕刻氣體可為例如(但不限於)CHF3、CF4、Cl2、BCl3和其混合氣體。
可按多個圖案形成經蝕刻的材料層,且所述多個圖案可為金屬圖案、半導體圖案、絕緣圖案等,例如半導體積體電路裝置的不同圖案。
半導體積體電路裝置中包含的圖案可為例如金屬線;半導體圖案;包含接觸孔、偏壓孔、鑲嵌溝槽在內的絕緣層等。
下文參考實例對本發明進行更詳細的說明。然而,這些實例只是例示性的,且本發明不限於此。
單體和聚合物的合成
聚合反應實例1
將20克(0.044莫爾)6,6'-(9H-芴-9,9-二基)雙(萘-2-醇)(6,6'-(9H-fluoren-9,9-diyl)bis(naphthalen-2-ol))和7.4克(0.044莫爾)1,4-雙(甲氧基甲基)苯(1,4-bis(methoxymethyl)benzene)相繼放置在燒瓶中,且使其溶解在43克丙二醇單甲基醚乙酸酯(PGMEA)中。接著,向其中添加0.12克(0.0008莫爾)硫酸二
乙酯(diethyl sulfate),並在90℃到120℃下攪拌混合物10小時到15小時。當每一小時從反應物獲取的樣本的重量平均分子量在3,200到4,500的範圍時,終止反應。
反應終止時,使反應產物冷卻到室溫且靜置。從其中去除上清液後,將剩餘在那裡的沉澱溶解在80克丙二醇單甲基醚乙酸酯(PGMEA)中,使用40克己烷、40克甲醇和40克蒸餾水來攪拌溶液,並將反應產物靜置(第一製程)。在這裡,再次去除獲得的上清液,將剩餘在那裡的沉澱溶解在40克丙二醇單甲基醚乙酸酯(PGMEA)中,將溶液添加到40克蒸餾水和400克甲醇中,並強力攪拌混合物,接著將混合物靜置(第二製程)。第一製程和第二製程被視為一個精製製程,且這種精製製程重複三次。將精製的聚合物溶解在80克丙二醇單甲基醚乙酸酯(PGMEA)中,並在減壓下去除溶液中剩餘的甲醇和蒸餾水,獲得由以下化學式4表示的化合物。
聚合反應實例2
將20克(0.044莫爾)6,6'-(9H-芴-9,9-二基)雙(萘-2-醇)和1克(0.033莫爾)多聚甲醛(paraform aldehyde)相繼放置在燒瓶中,且溶解在43克丙二醇單甲基醚乙酸酯(PGMEA)中。接著,向其中添加0.12克(0.0006莫爾)對甲苯磺酸(p-toluene
sulfonic acid,PTSA),並在90℃到120℃下攪拌混合物約5小時到10小時。當每一小時從反應物獲取的樣本具有3,000到4,200的重量平均分子量時,終止反應。
反應終止時,使反應產物冷卻到室溫且添加到40克蒸餾水和400克甲醇中,並強力攪拌混合物,接著將混合物靜置。從其中去除上清液後,將剩餘在那裡的沉澱溶解在80克丙二醇單甲基醚乙酸酯(PGMEA)中,將溶液添加到40克己烷、40克甲醇和40克蒸餾水中,並強力攪拌混合物,接著將混合物靜置(第一製程)。在這裡,再次從中去除上清液,將剩餘在那裡的沉澱溶解在40克丙二醇單甲基醚乙酸酯(PGMEA)中(第二製程)。第一製程和第二製程被視為一個精製製程,且所述精製製程總共重複三次。將精製的聚合物溶解在80克丙二醇單甲基醚乙酸酯(PGMEA)中,並在減壓下去除溶液中的甲醇和蒸餾水,獲得由以下化學式5表示的化合物。
聚合反應實例3
將20克(0.057莫爾)9,9-雙(4-羥基苯基)芴(9,9-bis(4-hydroxyphenyl)fluorene)和9.6克(0.057莫爾)1,4-雙(甲氧基甲基)苯相繼放置在燒瓶中,且溶解在51克丙二醇單甲基醚乙酸酯(PGMEA)中。接著,向其中添加0.15克(0.001莫爾)
亞硫酸二乙酯(diethyl sulfite),並在90℃到120℃下攪拌混合物5小時到12小時。當每一小時從反應物獲取的樣本具有3,500到4,200的重量平均分子量時,終止反應。
反應終止時,使反應產物冷卻到室溫且添加到40克蒸餾水和400克甲醇中,並強力攪拌混合物,接著將混合物靜置。從其中去除上清液後,將剩餘在那裡的沉澱溶解在80克丙二醇單甲基醚乙酸酯(PGMEA)中,將溶液添加到40克甲醇和40克蒸餾水中,並強力攪拌混合物,接著將混合物靜置(第一製程)。在這裡,去除從中獲得的上清液,並將剩餘在那裡的沉澱溶解在40克丙二醇單甲基醚乙酸酯(PGMEA)中(第二製程)。第一製程和第二製程被視為一個精製製程,且這種精製製程總共重複三次。將精製的聚合物溶解在80克丙二醇單甲基醚乙酸酯(PGMEA)中,並在減壓下去除溶液中剩餘的甲醇和蒸餾水,獲得由以下化學式6表示的化合物。
合成比較例1
第一步驟:取代基的引入反應(弗瑞德-克拉夫茨醯化,Friedel-Craft Acylation)
將1,4-環己烷二羰基二氯化物(1,4-cyclohexanedicarbonyl dichloride)(28.0克,0.1345莫爾)、甲氧基芘(methoxypyrene)(62.4克,0.269莫爾)和1,2-二氯乙烷(1,2-dichloroethane)(496
克)放置在燒瓶中以製備溶液。接著,將氯化鋁(17.9克,0.1345莫爾)緩慢添加到溶液中,並在室溫下攪拌混合物12小時。反應終止時,向其中添加甲醇,並過濾在其中形成的沉澱且對沉澱進行乾燥。
第二步驟:去甲基化反應
將所述化合物(6.00克,0.01001莫爾)、1-十二烷硫醇(1-dodecanethiol)(10.13克,0.05005莫爾)、氫氧化鉀(3.37克,0.06006莫爾)和N,N-二甲基甲醯胺(N,N-dimethylformamide)(30.3克)放置在燒瓶中且在120℃下攪拌8小時。冷卻反應混合物且用5%的鹽酸溶液將其中和到約pH 6到pH 7,並且過濾在其中形成的沉澱且對沉澱進行乾燥。
第三步驟:還原反應
將去甲基化的化合物(4.00克,0.00699莫爾)和四氫呋喃(tetrahydrofuran)(28.5克)放置在燒瓶中以製備溶液。接著,將硼氫化鈉(5.29克,0.1398莫爾)水溶液緩慢添加到所述溶液中,並在室溫下攪拌混合物24小時。反應終止時,用5%的鹽酸溶液將反應產物中和到約pH 7,接著用乙酸乙酯萃取,且對從中獲得的萃取物進行乾燥,獲得由化學式7表示的化合物。
硬罩幕組成物的製備
實例1
將根據聚合反應實例1的聚合物和6,6'-(9H-芴-9,9-二基)
雙(萘-2-醇)(FBN)以7:3的重量比溶解在通過以7:3(體積/體積)的比率混合丙二醇單甲基醚乙酸酯(PGMEA)和環己酮所獲得的混合溶劑中。隨後,過濾溶液,製備硬罩幕組成物。視所要厚度而定,基於硬罩幕組成物的全部重量調整聚合物和FBN的重量。
實例2
除使用根據聚合反應實例2的聚合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例3
除使用根據聚合反應實例3的聚合物以外,根據與實例1相同的方法製備硬罩幕組成物。
比較例1
將根據聚合反應實例1的聚合物溶解在通過以7:3(體積/體積)的比率混合丙二醇單甲基醚乙酸酯(PGMEA)和環己酮而製備的混合溶劑中。隨後,過濾溶液,製備硬罩幕組成物。視所要厚度而調整聚合物的量。
比較例2
除使用根據合成比較例1的化合物代替6,6'-(9H-芴-9,9-二基)雙(萘-2-醇)(FBN)以外,根據與實例1相同的方法製備硬罩幕組成物。
評估
評估1:間隙填充特徵和平坦化特徵
在經圖案化的矽晶圓上將根據實例1到實例3以及比較例1和比較例2的硬罩幕組成物分別旋塗到約2200埃厚。隨後,在熱板上在400℃下熱處理經塗佈的矽晶圓120秒,並且使用場發
射掃描電子顯微鏡(field emission scanning electronic microscope,FE-SEM)檢查間隙填充特徵和平坦化特徵。
通過觀測圖案的截面是否具有空隙來評估間隙填充特徵,並根據以下計算公式1來數字化平坦化特徵。由於高度h1與高度h2之間的差異越小表明平坦化特徵越佳,因此上述平坦化特徵是極佳的。
結果提供在表1中。
參看表1,與根據比較例1和比較例2的硬罩幕組成物相比,根據實例1到實例3的硬罩幕組成物展示出極佳的平坦化特徵並且還無空隙,因此所述組成物具有極佳的間隙填充特徵。
評估2:耐熱性
分別旋塗根據實例1到實例3以及比較例2的硬罩幕組成物(化合物含量:10.0重量%)以形成各個薄膜。隨後,在熱板
上在240℃下烘烤薄膜1分鐘,並測量其厚度。接著,再次在400℃下烘烤薄膜2分鐘,並再次測量其厚度。根據計算公式2,使用兩個厚度測量結果來計算硬罩幕薄膜的厚度減小率並數字化相對耐熱性。
[計算公式2](240℃下烘烤後的薄膜厚度-400℃下烘烤後的薄膜厚度)/240℃下烘烤後的薄膜厚度×100(%)
結果提供在表2中。
參看表2,與根據比較例2的硬罩幕組成物相比,由根據實例1到實例3的硬罩幕組成物形成的薄膜展示出較低的厚度減小率。因此,與根據比較例2的硬罩幕組成物相比,實例1到實例3的硬罩幕組成物展示出較高的耐熱性。
雖然已結合目前視為實用的例示性實施例來描述本發明,但應瞭解本發明不限於所公開的實施例,正相反,本發明意圖涵蓋包含在所附申請專利範圍的精神和範圍內的各種修改和同等配置。
h1、h2‧‧‧高度
Claims (12)
- 一種硬罩幕組成物,包括:聚合物,所述聚合物包含由以下化學式1a到化學式1c中的一者表示的部分;由以下化學式2表示的單體;以及溶劑:
- 如申請專利範圍第1項所述之硬罩幕組成物,其中所述聚合物進一步包括由以下化學式3表示的部分:[化學式3]*-R6-R7-*其中,在上述化學式3中,R6為選自所述族群1的一者;R7為選自所述族群2的一者。
- 如申請專利範圍第1項所述之硬罩幕組成物,其中所述聚合物具有1,000到200,000的重量平均分子量。
- 如申請專利範圍第1項所述之硬罩幕組成物,其中以100重量份所述溶劑計,所述聚合物和所述單體的量占5重量份到100重量份。
- 如申請專利範圍第1項所述之硬罩幕組成物,其中所述溶劑包括選自丙二醇單甲基醚乙酸酯、丙二醇單甲基醚、環己酮以及乳酸乙酯的至少一者。
- 如申請專利範圍第1項所述之硬罩幕組成物,其中所述硬罩幕組成物進一步包括交聯劑。
- 一種形成圖案的方法,包括:在基底上提供材料層;在所述材料層上塗覆如申請專利範圍第1項所述的硬罩幕組成物;熱處理所述硬罩幕組成物以形成硬罩幕層;在所述硬罩幕層上形成含矽薄層;在所述含矽薄層上形成光阻層;曝光且顯影所述光阻層以形成光阻圖案;使用所述光阻圖案選擇性地去除所述含矽薄層和所述硬罩幕層以暴露所述材料層的一部分;以及蝕刻所述材料層的暴露部分。
- 如申請專利範圍第7項所述之形成圖案的方法,其中使用旋塗法塗覆所述硬罩幕組成物。
- 如申請專利範圍第7項所述之形成圖案的方法,其中形成所述硬罩幕層的製程包括100℃到500℃下的熱處理。
- 如申請專利範圍第7項所述之形成圖案的方法,其進一步包括在所述含矽薄層上形成底部抗反射塗層。
- 如申請專利範圍第7項所述之形成圖案的方法,其中所述含矽薄層包括氮氧化矽、氮化矽或其組合。
- 一種半導體積體電路裝置,包括多個通過如申請專利範圍第7項所述之形成圖案的方法所形成的圖案。
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WO2013100409A1 (ko) * | 2011-12-30 | 2013-07-04 | 제일모직 주식회사 | 하드마스크 조성물용 모노머, 상기 모노머를 포함하는 하드마스크 조성물 및 상기 하드마스크 조성물을 사용하는 패턴형성방법 |
JP6652747B2 (ja) * | 2014-11-04 | 2020-02-26 | 日産化学株式会社 | アリーレン基を有するポリマーを含むレジスト下層膜形成組成物 |
KR101884447B1 (ko) | 2015-07-06 | 2018-08-01 | 삼성에스디아이 주식회사 | 모노머, 유기막 조성물, 유기막, 및 패턴형성방법 |
JP6712188B2 (ja) * | 2015-07-13 | 2020-06-17 | 信越化学工業株式会社 | レジスト下層膜形成用組成物及びこれを用いたパターン形成方法 |
KR101926023B1 (ko) | 2015-10-23 | 2018-12-06 | 삼성에스디아이 주식회사 | 막 구조물 제조 방법 및 패턴형성방법 |
WO2017115978A1 (ko) * | 2015-12-29 | 2017-07-06 | 삼성에스디아이 주식회사 | 유기막 조성물 및 패턴형성방법 |
KR101770749B1 (ko) | 2016-01-11 | 2017-08-23 | 최상준 | 반사방지용 하드마스크 조성물 |
KR102402748B1 (ko) * | 2017-11-10 | 2022-05-26 | 동우 화인켐 주식회사 | 하드마스크용 조성물 |
KR102397179B1 (ko) * | 2018-12-21 | 2022-05-11 | 삼성에스디아이 주식회사 | 하드마스크 조성물, 하드마스크 층 및 패턴 형성 방법 |
KR102230039B1 (ko) * | 2019-03-22 | 2021-03-19 | (주)코이즈 | 반사방지용 하드마스크 조성물 |
CN110041286B (zh) * | 2019-05-10 | 2021-03-19 | 福建泓光半导体材料有限公司 | 一种硬掩膜单体和组合物及图案形成方法 |
KR102296459B1 (ko) * | 2019-06-04 | 2021-09-02 | 에스케이하이닉스 주식회사 | 하드마스크용 화합물, 상기 화합물을 포함하는 하드마스크 조성물 및 이를 이용한 반도체 소자의 미세 패턴 형성 방법 |
CN113960880B (zh) * | 2021-11-02 | 2024-03-15 | 厦门恒坤新材料科技股份有限公司 | 一种硬掩膜组合物及其制备方法、形成图案的方法 |
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KR100655064B1 (ko) * | 2005-05-27 | 2006-12-06 | 제일모직주식회사 | 반사방지성을 갖는 하드마스크 조성물 |
KR100665758B1 (ko) * | 2005-09-15 | 2007-01-09 | 제일모직주식회사 | 반사방지성을 갖는 하드마스크 조성물 |
JP4659678B2 (ja) * | 2005-12-27 | 2011-03-30 | 信越化学工業株式会社 | フォトレジスト下層膜形成材料及びパターン形成方法 |
JP4662063B2 (ja) * | 2006-05-25 | 2011-03-30 | 信越化学工業株式会社 | フォトレジスト下層膜形成材料及びパターン形成方法 |
US7745104B2 (en) * | 2006-08-10 | 2010-06-29 | Shin-Etsu Chemical Co., Ltd. | Bottom resist layer composition and patterning process using the same |
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 |
KR100908601B1 (ko) * | 2007-06-05 | 2009-07-21 | 제일모직주식회사 | 반사방지 하드마스크 조성물 및 이를 이용한 기판상 재료의패턴화 방법 |
KR100930673B1 (ko) * | 2007-12-24 | 2009-12-09 | 제일모직주식회사 | 반사방지 하드마스크 조성물 및 이를 이용한재료의 패턴화 방법 |
JP5336306B2 (ja) * | 2008-10-20 | 2013-11-06 | 信越化学工業株式会社 | レジスト下層膜形成方法、これを用いたパターン形成方法、及びレジスト下層膜材料 |
TWI400575B (zh) * | 2008-10-28 | 2013-07-01 | Shinetsu Chemical Co | 光阻劑下層膜形成材料及圖案形成方法 |
JP5229278B2 (ja) * | 2010-06-21 | 2013-07-03 | 信越化学工業株式会社 | ナフタレン誘導体、レジスト下層膜材料、レジスト下層膜形成方法及びパターン形成方法 |
JP5556773B2 (ja) * | 2010-09-10 | 2014-07-23 | 信越化学工業株式会社 | ナフタレン誘導体及びその製造方法、レジスト下層膜材料、レジスト下層膜形成方法及びパターン形成方法 |
FI20115628L (fi) * | 2011-06-20 | 2012-12-21 | Silecs Oy | Uusi polymeerikoostumus ja menetelmä sen valmistamiseksi |
KR101655394B1 (ko) * | 2013-04-25 | 2016-09-07 | 제일모직 주식회사 | 레지스트 하층막용 조성물, 이를 사용한 패턴 형성 방법 및 상기 패턴을 포함하는 반도체 집적회로 디바이스 |
US9152051B2 (en) * | 2013-06-13 | 2015-10-06 | Az Electronics Materials (Luxembourg) S.A.R.L. | Antireflective coating composition and process thereof |
CN104253024B (zh) * | 2013-06-27 | 2017-07-28 | 第一毛织株式会社 | 硬掩模组合物、使用其形成图案的方法以及包括该图案的半导体集成电路装置 |
-
2013
- 2013-12-31 KR KR1020130169260A patent/KR20150079199A/ko not_active Application Discontinuation
-
2014
- 2014-11-05 US US14/533,200 patent/US20150187566A1/en not_active Abandoned
- 2014-11-27 CN CN201410705160.6A patent/CN104749886B/zh active Active
- 2014-12-05 TW TW103142270A patent/TWI532785B/zh active
Also Published As
Publication number | Publication date |
---|---|
KR20150079199A (ko) | 2015-07-08 |
US20150187566A1 (en) | 2015-07-02 |
CN104749886A (zh) | 2015-07-01 |
CN104749886B (zh) | 2020-04-21 |
TW201525057A (zh) | 2015-07-01 |
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