TWI686381B - 光阻劑組合物及方法 - Google Patents
光阻劑組合物及方法 Download PDFInfo
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- TWI686381B TWI686381B TW107147704A TW107147704A TWI686381B TW I686381 B TWI686381 B TW I686381B TW 107147704 A TW107147704 A TW 107147704A TW 107147704 A TW107147704 A TW 107147704A TW I686381 B TWI686381 B TW I686381B
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 170
- 239000000203 mixture Substances 0.000 title claims abstract description 141
- 238000000034 method Methods 0.000 title claims description 38
- 229920000642 polymer Polymers 0.000 claims abstract description 126
- 239000000654 additive Substances 0.000 claims abstract description 39
- 230000000996 additive effect Effects 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000011159 matrix material Substances 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000000758 substrate Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 230000005855 radiation Effects 0.000 claims description 13
- 230000003213 activating effect Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 5
- 239000008199 coating composition Substances 0.000 claims description 4
- 229920002313 fluoropolymer Polymers 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 84
- 239000000463 material Substances 0.000 description 24
- -1 1-methylcyclopentyl Chemical group 0.000 description 21
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 20
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- 229910052731 fluorine Inorganic materials 0.000 description 16
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- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 7
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- 239000011593 sulfur Substances 0.000 description 5
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
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- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
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Classifications
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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
- G03F7/11—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
- G03F7/004—Photosensitive materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
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Abstract
提供適用於各種應用之新型光阻劑及面塗層組合物。在一個態樣中,提供新型光阻劑組合物,其包括:(a)第一基質聚合物;(b)一或多種酸產生劑;及(c)一或多種式(I)及/或式(II)之添加劑化合物。
Description
本發明一般係關於電子器件之製造。更具體而言,本發明係關於光阻劑及面塗層組合物,且關於允許形成精細圖案之光微影製程。本發明組合物尤其適用於浸沒式微影製程以形成半導體器件。
光阻劑為用於將影像轉移至基板之感光膜。在基板上形成光阻劑塗層且隨後光阻劑層經由光遮罩暴露於活化輻射源。在曝光之後,使光阻劑顯影,以得到允許選擇性處理基板之凸紋影像。
已經做出了相當大的努力來擴展正型光阻劑顯影,包含浸沒式微影之實際解析能力。一個此類實例涉及傳統上正型的化學增幅型光阻劑之負型顯影(negative tone development,NTD),其係經由使用特定顯影劑,典型地,有機顯影劑,諸如酮、酯或醚,留下由不溶性曝光區域產生的圖案。舉例而言,參見U.S. 6790579。
已採用某些添加劑來嘗試改良光阻劑解析度。參見JPH11337722A;US2007190451;EP1702962B1;US20060172149;US20130177853;US20130344436;US20140038102;US6132931;US20120077120;US6391521;US9563123。
在浸沒式微影中,浸液與光阻劑層之間的直接接觸可引起光阻劑之組分浸入至浸液中。此浸入可造成光學透鏡之污染且引起浸液之有效折射率及透射性質發生改變。為了改善這個問題,已經提出在光阻劑層上使用面塗層作為浸液與下伏光阻劑層之間的屏障。然而,在浸沒式微影中使用面塗層存在各種挑戰。視諸如面塗層折射率、厚度、酸度、與光阻劑之化學相互相用及浸泡時間而定,面塗層可影響例如製程窗口、臨界尺寸(critical dimension,CD)變化及光阻劑輪廓。另外,例如,由於阻止恰當光阻劑圖案形成的微橋接缺陷,使用面塗層會不利地影響器件良率。
為了改良面塗層材料之效能,已經例如在以下中提出使用自隔離面塗層組合物以形成分級面塗層:《用於浸沒式微影的自分離材料(Self-segregating Materials for Immersion Lithography
)》, Daniel P. Sanders等人, 《光阻劑材料及處理技術進展XXV(Advances in Resist Materials and Processing Technology XXV)》, 《SPIE會議論文集(Proceedings of the SPIE)》, 第6923卷, 第692309-1至692309-12頁 (2008)。亦參見US20120264053。
電子器件製造商致力於不斷提高圖案化光阻劑影像之解析度。期望有一種可提供增強之成像能力的新型組合物。
現提供適用於光微影應用,包含浸沒式微影製程之新型組合物。
在較佳實施例中,本發明組合物可表現出提高的儲存壽命,包含在長期儲存時組合物之降解相對減少。舉例而言,參見以下實例中闡述之比較資料。
更確切而言,在第一態樣中,提供光阻劑組合物,其包括:(a)第一基質聚合物;(b)一或多種酸產生劑;及(c)一或多種具有下式(I)或式(II)結構之添加劑化合物:其中在所述式(I)及式(2)中之每一者中,R1
及R2
各自為相同或不同的非氫取代基,諸如視情況取代之烷基、視情況取代之烷氧基、視情況取代之硫烷基、視情況取代之碳環芳基或視情況取代之雜芳族基團, 或R1
或R2
可經由基團Z連接,其中Z為單鍵或選自以下之基團:C=O、S(O)、S(O)2、-C(=O)O-、-C(=O)NH-、-C(=O)-C(=O)-、-O-、CHOH、CH2
、S、-B-; 各式中之X為下列中之一者:其中R3
為非氫取代基;及 各n為1至5之正整數。R1
及R2
之較佳的視情況之取代包含例如經-OY、-NO2
、-CF3
-、-C(=O)NHY、-C(=O)-C(=O)-Y、CHOY、CH2
Y、-SY、-B(Y)n、-NHC(=O)Y、-(C=O)OY取代(其中Y為直鏈或分支鏈、飽和或不飽和烷基;氟烷烴或烯烴或炔烴;或碳環芳基或雜芳族基團)。
在較佳態樣中,光阻劑組合物將含有不同於第一聚合物之第二聚合物。較佳地,此類第二聚合物將包括氟取代,諸如一或多個氟C1-12
烷基。在特定態樣中,第二聚合物可包括下式(3)之重複單元:其中在式(3)中,R4
及R5
各自獨立地為氫、鹵素、C1-8
烷基或C1-8
鹵烷基,諸如氟C1-8
烷基,且L為視情況取代之多價連接基團,諸如-(CH2
)q-,其中q為1、2、3、4、5或6。
在較佳態樣中,添加劑化合物包括一或多個酸酐部分。較佳的添加劑化合物亦可為鹵化的添加劑化合物,尤其氟化的添加劑化合物。較佳的添加劑化合物亦可包括磺酸酯基。
在又一態樣中,提供用於光阻劑層上之面塗層組合物,較佳的面塗層組合物可包括(a)第一基質聚合物;(b)不同於第一聚合物之第二聚合物;及(c)一或多種具有下式(I)或式(II)結構之添加劑化合物:其中,在所述式(I)及式(2)中之每一者中,R1
、R2
、X及R3
以及n與以上定義相同。
較佳地,面塗層組合物之第二聚合物將包括氟取代,諸如一或多個氟C1-12
烷基。在特定態樣中,第二聚合物可包括下式(3)之重複單元:其中在式(3)中,R4
及R5
各自獨立地為氫、鹵素、C1-8
烷基或C1-8
鹵烷基,諸如氟C1-8烷基,且L為視情況取代之多價連接基團,諸如-(CH2
)q-,其中q為1、2、3、4、5或6。
在較佳態樣中,添加劑化合物包括一或多個酸酐部分。較佳的添加劑化合物亦可為鹵化的添加劑化合物,尤其氟化的添加劑化合物。較佳的添加劑化合物亦可包括磺酸酯基。
根據又一態樣,提供經塗覆之基板。經塗覆之基板包括基板及在基板表面上的本發明之光阻劑組合物層。亦提供包括基板及本發明之面塗層組合物層的經塗覆之基板。
面塗層組合物典型地將塗覆在光阻劑組合物層上,其可為本發明之光阻劑組合物。
根據再一態樣,提供形成光微影圖案之方法。所述方法宜包括:(a)提供包括一或多個待在基板表面上圖案化之層的基板;(b)在待圖案化之一或多個層上施加一層本發明之光阻劑組合物;(c)以圖案方式將光阻劑組合物層暴露於活化輻射;及(d)將顯影劑施加至光阻劑組合物層上,從而產生光阻劑凸紋影像。適當地,在顯影之前,在曝光後烘烤過程中對曝光之光阻劑組合物層進行熱處理。
在一較佳態樣中,藉由顯影劑移除光阻劑層之未曝光部分,在一或多個待圖案化之層上留下光阻劑圖案。以圖案方式曝光可藉由浸沒式微影或者使用乾式曝光技術來進行。在某些態樣中,植入及EUV微影製程亦為較佳的。
另外提供之方法包含形成光微影圖案,其包括:(a)提供包括一或多個待在基板表面上圖案化之層的基板;(b)在待圖案化之一或多個層上施加一層光阻劑組合物;(c)在光阻劑組合物層之上或上方施加一層本發明之面塗層組合物;(d)以圖案方式將面塗層組合物層及光阻劑組合物層兩者暴露於活化輻射;及(e)將顯影劑施加至成像的經塗覆之基板上,從而產生光阻劑凸紋影像。適當地,在顯影之前,在曝光後烘烤過程中對曝光之光阻劑組合物層及面塗層組合物層進行熱處理。在各個態樣中,以圖案方式曝光可藉由浸沒式微影或者使用乾式曝光技術來進行。在某些態樣中,植入及EUV微影製程亦為較佳的。
本發明亦包含聚合物,其包括與聚合物主鏈間隔開之反應性含氮部分,其中含氮部分在光阻劑組合物之微影處理期間產生鹼性裂解產物。
亦提供由所揭示之方法形成的電子器件。
以下揭示本發明之其他態樣。
用於光阻劑及面塗層組合物的較佳添加劑化合物可為聚合的或非聚合的,其中非聚合添加劑化合物對於許多應用而言為較佳的。較佳的添加劑化合物之分子量相對較低,例如分子量小於或等於3000,更佳≤ 2500、≤ 2000、≤ 1500、≤ 1000、≤ 800或甚至更佳≤ 500。
較佳的添加劑化合物在有機光阻劑溶劑,諸如乳酸乙酯、丙二醇甲醚乙酸酯(propylene glycol methyl ether acetate,PGMEA)、環己酮及其混合物中表現出良好之溶解度。
在一個態樣中,包括封端或掩蔽之酸基團,諸如酸酐基團的添加劑化合物為較佳的。
適用於本發明之添加劑化合物通常可商購獲得或可易於合成。舉例而言,參見以下實例。
按光阻劑或面塗層組合物之總固體重量計(總固體為除溶劑外之所有組合物組分),本發明之光阻劑及面塗層組合物可宜包括一或多種添加劑化合物,其量在寬範圍內,諸如0.005至20重量%,更佳地,按組合物之總固體總重量計,量為0.01、0.05、0.1、0.02、0.3、0.4、0.5或1至1、2、3、4、5或10重量%,且更典型地,量為0.01、0.05、0.1、0.02、0.3、0.4、0.05或1至5、6、7、8、9或10重量%。
在較佳組合物中,在塗覆光阻劑組合物期間,第一聚合物可朝向光阻劑塗層之上表面遷移。在某些系統中,此可形成實質上由第一聚合物製成的表面層。不受任何理論的束縛,咸信第一聚合物之氮(鹼性)部分有助於控制散射光或漫射光,從而使得可減少圖案化缺陷,諸如線及溝槽圖案形成之情況下的缺失接觸孔及微橋接缺陷。在曝光及曝光後烘烤(post exposure bake,PEB)之後,可使光阻劑塗層顯影,其包含在包括有機溶劑之顯影劑中。有機顯影劑移除光阻劑層之未曝光區域及曝光區域之表面層。當在乾式微影或浸沒式微影製程中使用所述組合物時,可達成本發明光阻劑組合物之益處。當用於浸沒式微影時,較佳的光阻劑組合物可進一步表現出光阻劑材料向浸液中的遷移(浸入)減少,其亦為添加劑聚合物遷移至光阻劑表面的結果。值得注意的是,此可在不於光阻劑上使用面塗層之情況下達成。
光阻劑可在各種輻射波長下使用,例如,小於400 nm、小於300或小於200 nm之波長,或較佳248 nm、193 nm及EUV(例如,13.5 nm)曝光波長。所述組合物可進一步用於電子束(electron beam/E-beam)曝光過程。
本發明之光阻劑組合物較佳為化學增幅型材料。在較佳實施例中,光阻劑組合物包括一或多種第二或基質聚合物(其不同於第一聚合物),其包括酸不穩定基團。酸不穩定基團為在酸存在下易於經歷去保護反應的化學部分。作為光阻劑組合物層之一部分的第二或基質聚合物在本文所述之顯影劑中經歷溶解度之變化,此係由於在微影處理期間,尤其在軟烘烤、暴露於活化輻射及曝光後烘烤後,與光酸(photoacid)及/或熱酸產生劑所產生的酸反應。此係由光酸誘導的酸不穩定基團之裂解引起的,導致第二聚合物之極性發生變化。舉例而言,酸不穩定基團可選自碳酸第三烷酯、第三烷基酯、第三烷基醚、縮醛及縮酮。較佳地,酸不穩定基團為酯基,其含有共價連接至第二基質聚合物的酯的羧基氧的第三非環狀烷基碳或第三脂環族碳。此類酸不穩定基團之裂解導致羧酸基團的形成。合適的含有酸不穩定基團之單元包含例如酸不穩定(烷基)丙烯酸酯單元,諸如(甲基)丙烯酸第三丁酯、(甲基)丙烯酸1-甲基環戊酯、(甲基)丙烯酸1-乙基環戊酯、(甲基)丙烯酸1-異丙基環戊酯、(甲基)丙烯酸1-丙基環戊酯、(甲基)丙烯酸1-甲基環己酯、(甲基)丙烯酸1-乙基環己酯、(甲基)丙烯酸1-異丙基環己酯、(甲基)丙烯酸1-丙基環己酯、甲基金剛烷基(甲基)丙烯酸第三丁酯(t-butyl methyladamantyl(meth)acrylate)、(甲基)丙烯酸乙基葑酯及類似者,及其他環狀(包含脂環族)及非環狀(烷基)丙烯酸酯。縮醛及縮酮酸不穩定基團可在鹼溶性基團,諸如羧基或羥基的末端處經氫原子取代,以便與氧原子鍵合。當產生酸時,酸裂解縮醛或縮酮基團與縮醛型可酸解離的溶解抑制基團所鍵合的氧原子之間的鍵。例示性的此類酸不穩定基團例如描述於美國專利第US6057083號、第US6136501號及第US8206886號及歐洲專利公開案第EP01008913A1號及第EP00930542A1號中。縮醛及縮酮基團作為糖衍生物結構之一部分亦為合適的,其裂解將引起羥基之形成,例如,美國專利申請案第US2012/0064456A1號中描述的彼等者。
對於在200 nm或大於200 nm,諸如248 nm之波長下成像,合適的樹脂材料(包含用作本發明光阻劑組合物之第二聚合物)包含例如含有酸不穩定基團的酚醛樹脂。尤其較佳的此類樹脂包含:(i)含有乙烯基苯酚及如上所述的酸不穩定(烷基)丙烯酸酯的聚合單元的聚合物,諸如美國專利第6,042,997號及第5,492,793號中所述之聚合物;(ii)含有乙烯基苯酚、不含羥基或羧基環取代基的視情況取代之乙烯基苯基(例如苯乙烯)及如上所述的酸不穩定(烷基)丙烯酸酯的聚合單元的聚合物,諸如美國專利第6,042,997號中所述之聚合物;(iii)含有重複單元(其包括將與光酸反應的縮醛或縮酮部分)及視情況選用之芳族重複單元,諸如苯基或酚基的聚合物,此類聚合物描述於美國專利第5,929,176號及第6,090,526號中;及(i)及/或(ii)及/或(iii)之共混物。
對於在某些小於200 nm波長,諸如193 nm下成像,第二或基質聚合物典型地實質上不含(例如小於15莫耳%),較佳完全不含苯基、苯甲基或其他芳族基團,其中此類基團為高輻射吸收型。實質上或完全不含芳族基團的合適聚合物揭示於歐洲專利公開案第EP930542A1號及美國專利第6,692,888號及第6,680,159號中。
其他合適的第二或基質聚合物包含例如含有非芳族環烯烴(內環雙鍵),諸如視情況取代之降冰片烯的聚合單元的彼等者,例如,美國專利第5,843,624號及第6,048,664號中所述之聚合物。再其他合適的基質聚合物包含含有聚合酸酐單元,尤其聚合順丁烯二酸酐及/或衣康酸酐單元之聚合物,諸如歐洲公開申請案EP01008913A1及美國專利第6,048,662號中所揭示。
含有含雜原子,尤其氧及/或硫之重複單元(但酸酐除外,亦即所述單元不含酮環原子)的樹脂亦適用作第二或基質聚合物。雜脂環單元可稠合至聚合物主鏈,且可包括諸如藉由聚合降冰片烯基團得到的稠合碳脂環單元及/或諸如藉由聚合順丁烯二酸酐或衣康酸酐得到的酸酐單元。此類聚合物揭示於國際公開案第WO0186353A1號及美國專利第6,306,554號中。其他合適的含有雜原子基團的基質聚合物包含含有經一或多個含雜原子(例如氧或硫)的基團例,例如羥基萘基取代的聚合碳環芳基單元的聚合物,諸如美國專利第7,244,542號中所揭示。
在小於200 nm波長,諸如193 nm及EUV(例如13.5 nm)之情況下,第二或基質聚合物可包含含有內酯部分之單元,以控制第二基質聚合物及光阻劑組合物之溶解速率。適用於含有內酯部分之第二或基質聚合物的單體包含例如以下:
第二或基質聚合物可包含一或多種上述類型之額外單元。典型地,第二或基質聚合物之額外單元將包含與用於單體(其用來形成聚合物之其他單元)的彼等可聚合基團相同或類似的可聚合基團,但是在相同的聚合物主鏈中可包含其他不同的可聚合基團。
在較佳態樣中,第二或基質聚合物與下文所述第一或添加劑聚合物相比具有較高之表面能,且應實質上不可與第二聚合物混溶。由於表面能之差異,第二聚合物與第一聚合物之分離可在旋塗期間發生。第二或基質聚合物之合適表面能典型地為20至50 mN/m,較佳30至40 mN/m。
如所論述,在較佳態樣中,第二聚合物可具有鹵素取代,諸如氟取代,包含氟烷基,例如具有六氟丙醇取代的聚合物。
適用於本發明之光阻劑組合物的第二或基質聚合物可商購獲得且可由本領域中熟習此項技術者容易地製得。第二聚合物以足以使光阻劑之曝光塗層可在合適之顯影劑溶液中顯影的量存在於光阻劑組合物中。通常,按光阻劑組合物之總固體計,第二聚合物以50至95重量%的量存在於組合物中。第二聚合物之重量平均分子量Mw
典型地小於100,000,例如3000至100,000,更典型地,3000至15,000。上述第二聚合物中之兩者或多於兩者的共混物可宜用於本發明之光阻劑組合物中。
第一或添加劑聚合物較佳為具有比第二聚合物之表面能要低的表面能的材料,且應實質上不與第二聚合物混溶。以此方式,促進第一聚合物在塗覆過程中向所施加之光阻劑層之頂部或上部的分離或遷移。儘管第一聚合物之所需表面能將視特定第二聚合物及其表面能而定,但第一聚合物表面能典型地為18至40 mN/m、較佳20至35 mN/m且更佳29至33 mN/m。當第一聚合物在塗覆過程中遷移至光阻劑層之上表面時,可較佳地,第一聚合物與在光阻劑層表面正下方之第二或基質聚合物之間存在一些互混。咸信此類互混有助於藉由減少或消除由於漫射光而在第二或基質聚合物附近的暗區中產生的酸來降低光阻劑層的表面抑制。互混程度將視例如第二或基質聚合物(matrix polymer,MP)與第一或添加劑聚合物(additive polymer,AP)之間的表面能(surface energy,SE)的差(ΔSE = SEMP
- SEAP
)而定。對於給定的第一或基質及第二或添加劑聚合物,互混程度可隨著ΔSE之減小而增加。ΔSE典型地為2至32 mN/m,較佳5至15 mN/m。
如所論述,適用於光阻劑組合物之第一或添加劑聚合物為具有複數個不同重複單元,例如兩個、三個或四個不同重複單元之共聚物。
第一聚合物較佳不含矽。在某些蝕刻劑中,含矽聚合物表現出比有機光阻劑聚合物低得多的蝕刻速率。因此,含矽第一聚合物在基於有機第二聚合物的光阻劑層的表面處聚集會在蝕刻過程中引起錐形缺陷。第一聚合物可含有氟或可不含氟。較佳第一聚合物在用於調配光阻劑組合物的相同有機溶劑中為可溶的。較佳第一聚合物在用於負型顯影過程的有機顯影劑中亦將為可溶的或在曝光後烘烤(例如120℃持續60秒)之後變得可溶。
如所論述,較佳第一聚合物可含有由對應於下式(I)之一或多種單體形成的單元: X1
-R1
-X2
-R2
-X3
(I) 其中X1
為可聚合官能基,諸如丙烯酸酯或烷基丙烯酸酯,諸如甲基丙烯酸酯;R1
可為視情況取代之直鏈、分支鏈或環狀脂族基團或芳族基團,宜為C1-15
烷基且視情況經氟化;X2
為鹼性部分,諸如氮,且可為R1
的組分或與R1
一起使用(例如R1
及X2
可組合形成哌啶基部分);R2
為酸不穩定基團;且X3
可為視情況取代之直鏈、分支鏈或環狀脂族基團或芳族基團。
例如,可聚合官能基X1
可選自下列通式(P-1)、通式(P-2)及通式(P-3):其中R2
選自氫、氟以及氟化及非氟化的C1至C3烷基;且X為氧或硫;其中R3
選自氫、氟以及氟化及非氟化的C1至C3烷基;及其中m為0至3之整數。
例示性的合適單體如下所述,但不限於此等結構。
較佳地,第一聚合物亦包括一或多種由對應於下列通式(I-1)之單體形成的額外不同單元(第二單元):其中:R2
選自氫、氟以及氟化及非氟化的C1至C3烷基;且X為氧或硫;且R4
選自取代及未取代之C1至C20直鏈、分支鏈及環狀烴,較佳氟化及非氟化的C1至C15烷基,更佳氟化及非氟化的C3至C8烷基且最佳氟化及非氟化的C4至C5烷基,其中當用於浸沒式微影時,較佳R4
為分支鏈的以提供較大的水後退接觸角(water receding contact angle),且鹵烷基及鹵醇,諸如氟烷基及氟醇的R4
取代為合適的。
如所論述,單體、聚合物及其他材料的各個部分可視情況經取代(或陳述為「取代或未取代」)。「取代的」取代基可在一或多個可用位置,典型地,1、2或3個位置處經一或多個合適的基團取代,諸如鹵素(尤其F、Cl或Br);氰基;硝基;C1-8
烷基;C1-8
烷氧基;C1-8
烷基硫基;C1-8
烷基磺醯基;C2-8
烯基;C2-8
炔基;羥基;硝基;烷醯基,諸如C1-6
烷醯基,例如醯基;鹵烷基,尤其C1-8
鹵烷基,諸如CF3
;-CONHR、-CONRR',其中R及R'為視情況取代之C1-8
烷基;-COOH、COC、>C=O及類似者。
光阻劑組合物宜包含單一第一聚合物,但可視情況包含一或多種額外的第一聚合物。適用於光阻劑組合物的聚合物及單體可商購獲得及/或可由本領域中熟習此項技術者容易地製得。
第一聚合物典型地以相對較少的量,例如以按光阻劑組合物之總固體計,0.1至10重量%,較佳0.5至5重量%,更佳1至3重量%的量存在於光阻劑組合物中。例如,第一或添加劑聚合物之含量將視光阻劑層中酸產生劑之含量、第一聚合物中含氮基團之含量以及微影為乾式還是浸沒型製程而定。例如,浸沒式微影之第一聚合物下限通常由防止光阻劑組分浸入的需要來決定。過高的第一聚合物含量典型地會導致圖案劣化。添加劑聚合物之重量平均分子量通常小於400,000,較佳3000至50,000,更佳3000至25,000。適用於製備用於本發明之光阻劑組合物的第一聚合物的第一聚合物及單體可商購獲得及/或可由本領域中熟習此項技術者製得。
較佳光阻劑組合物可包括一或多種光酸產生劑(PAG),其以足以在暴露於活化輻射後在光阻劑組合物的塗層中產生潛影的量採用。例如,按光阻劑組合物之總固體計,光酸產生劑將宜以約1至20重量%的量存在。通常,較少量的光活性組分將適合於化學增幅型光阻劑。
面塗層組合物亦可包括一或多種酸產生劑化合物,其包含一或多種光酸產生劑化合物及/或一或多種熱酸產生劑化合物。本文揭示之PAG以及其用於光阻劑組合物的量適合於面塗層組合物。相對較少量的PAG通常適合於面塗層組合物。
合適的PAG為化學增幅型光阻劑領域中已知的且包含例如:鎓鹽,例如三苯基鋶三氟甲烷磺酸鹽、(對第三丁氧基苯基)二苯基鋶三氟甲烷磺酸鹽、三(對第三丁氧基苯基)鋶三氟甲烷磺酸鹽、三苯基鋶對甲苯磺酸鹽;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;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。可使用此類PAG中之一或多者。
適合於本發明的光阻劑及面塗層組合物的溶劑包含例如:二醇醚,諸如2-甲氧基乙基醚(二乙二醇二甲醚(diglyme))、乙二醇單甲醚及丙二醇單甲醚;丙二醇單甲醚乙酸酯;乳酸酯,諸如乳酸甲酯及乳酸乙酯;丙酸酯,諸如丙酸甲酯、丙酸乙酯、乙氧基丙酸乙酯及甲基-2-羥基異丁酸酯;溶纖劑酯,諸如溶纖劑乙酸甲酯;芳族烴,諸如甲苯及二甲苯;及酮,諸如甲基乙基酮、環己酮及2-庚酮。溶劑之共混物,諸如上述溶劑中之兩者、三者或大於三者的共混物亦為合適的。按光阻劑組合物之總重量計,溶劑典型地以90至99重量%,更典型地為95至98重量%的量存在於組合物中。
舉例而言,用於光阻劑組合物的其他視情況選用之添加劑包含光化及對比染料、抗條紋劑、增塑劑、增速劑、敏化劑及類似者。按光阻劑組合物之總固體計,此類視情況選用之添加劑(若使用)通常以較少量,諸如0.1至10重量%存在於組合物中,但按光阻劑組合物之總固體計,填料及染料可以相對較大的濃度,例如5至30重量%存在。
本發明之光阻劑組合物的較佳的視情況選用之添加劑為添加的鹼,其可增強所顯影的光阻劑凸紋影像的解析度。合適的鹼性淬滅劑包含例如直鏈及環狀醯胺及其衍生物,諸如N,N-雙(2-羥乙基)特戊醯胺(pivalamide)、N,N-二乙基乙醯胺、N1,N1,N3,N3-四丁基丙二醯胺、1-甲基氮雜環庚烷-2-酮、1-烯丙基氮雜環庚烷-2-酮及1,3-二羥基-2-(羥甲基)丙醯-2-基胺基甲酸第三丁酯;芳族胺,諸如吡啶及二第三丁基吡啶;脂族胺,諸如三異丙醇胺、正第三丁基二乙醇胺、三(2-乙醯氧基-乙基)胺、2,2',2'',2'''-(乙烷-1,2-二基雙(氮烷三基))四乙醇及2-(二丁胺基)乙醇、2,2',2''-次氮基三乙醇;環狀脂族胺,諸如1-(第三丁氧基羰基)-4-羥基哌啶、1-吡咯啶甲酸第三丁酯、2-乙基-1H-咪唑-1-甲酸第三丁酯、哌嗪-1,4-二甲酸二第三丁酯及N (2-乙醯氧基-乙基)嗎啉。在此等鹼性淬滅劑中,較佳1-(第三丁氧基羰基)-4-羥基哌啶及三異丙醇胺。添加的鹼適合以相對較少的量使用,例如,相對於PAG為1至20重量%,更通常地相對於PAG為5至15重量%。
可根據本發明使用的光阻劑及面塗層組合物通常按照已知程序來製備。例如,本發明之光阻劑可藉由將光阻劑之組分溶解於合適之溶劑中而製備為塗層組合物,所述溶劑例如為以下中之一或多者:二醇醚,諸如2-甲氧基乙基醚(二乙二醇二甲醚)、乙二醇單甲醚、丙二醇單甲醚;丙二醇單甲醚乙酸酯;乳酸酯,諸如乳酸乙酯或乳酸甲酯,其中乳酸乙酯為較佳的;丙酸酯,尤其丙酸甲酯、丙酸乙酯及乙氧基丙酸乙酯;溶纖劑酯,諸如溶纖劑乙酸甲酯;芳族烴,諸如甲苯或二甲苯;或酮,諸如甲基乙基酮、環己酮及2-庚酮。光阻劑之所需總固體含量將視如組合物中的特定聚合物、最終層厚及曝光波長之因素而定。按光阻劑組合物之總重量計,光阻劑之固體含量通常在1至10重量%、更通常為2至5重量%之間變化。
本發明進一步提供使用本發明之光阻劑形成光阻劑凸紋影像及製造電子器件之方法。本發明亦提供包括塗有本發明之光阻劑組合物的基板的新穎製品。
在微影處理中,可將光阻劑組合物施加在各種基板上。基板可為諸如半導體的材料,諸如矽或化合物半導體(例如III-V或II-VI)、玻璃、石英、陶瓷、銅及類似者。典型地,基板為半導體晶圓,諸如單晶矽或化合物半導體晶圓,且可具有形成於其表面上的一或多個層及圖案化特徵。可在基板上提供一或多個待圖案化的層。例如,當期望在基板材料中形成溝槽時,視情況地,底層基板材料自身可經圖案化。在圖案化基礎基板材料自身之情況下,圖案應視為形成在基板層中。
所述層可包含例如一或多個導電層,諸如鋁、銅、鉬、鉭、鈦、鎢、合金、此類金屬的氮化物或矽化物、摻雜非晶矽或摻雜多晶矽的層;一或多種介電層,諸如氧化矽、氮化矽、氮氧化矽或金屬氧化物的層;半導體層,諸如單晶矽,及其組合。待蝕刻的層可藉由各種技術形成,例如化學氣相沈積(chemical vapor deposition,CVD),諸如電漿增強型CVD、低壓CVD或磊晶生長(epitaxial growth);物理氣相沈積(physical vapor deposition,PVD),諸如濺射或蒸發;或電鍍。待蝕刻的一或多個層102的特定厚度將視材料及形成的特定器件而變化。
視待蝕刻的特定層、膜厚及待使用的光微影材料及製程而定,可能需要在所述層上安置硬遮罩層及/或底部抗反射塗層(bottom antireflective coating,BARC),在其上塗覆光阻劑層。例如,在極薄光阻劑層之情況下,其中待蝕刻的層需要顯著之蝕刻深度,及/或其中特定蝕刻劑具有不良的光阻劑選擇性,可能期望使用硬遮罩層。當使用硬遮罩層時,待形成之光阻劑圖案可轉移至硬遮罩層,其轉而可用作蝕刻底層之遮罩。合適的硬遮罩材料及形成方法在此項技術中已知。典型的材料包含例如鎢、鈦、氮化鈦、氧化鈦、氧化鋯、氧化鋁、氧氮化鋁、氧化鉿、非晶碳、氮氧化矽及氮化矽。硬遮罩層可包含單層或複數個不同材料之層。例如,可藉由化學或物理氣相沈積技術形成硬遮罩層。
在基板及/或底層將在光阻劑曝光期間另外反射大量的入射輻射使得所形成的圖案的品質將受到不利影響之情況下,底部抗反射塗層可為所期望的。此類塗層可改良聚焦深度、曝光寬容度、線寬均勻性及CD控制。典型地,當光阻劑暴露於深紫外光(300 nm或小於300 nm),例如KrF準分子雷射(248 nm)或ArF準分子雷射(193 nm)時,使用抗反射塗層。抗反射塗層可包括單層或複數個不同層。合適的抗反射材料及形成方法在此項技術中已知。抗反射材料可商購獲得,例如,由羅門哈斯電子材料LLC(Rohm and Haas Electronic Materials LLC)(美國馬薩諸塞州馬波羅(Marlborough, MA USA))以AR™商標出售的彼等者,諸如AR™40A及AR™124抗反射材料。
將由如上所述的本發明之組合物形成的光阻劑層施加至基板上。通常藉由旋塗將光阻劑組合物施加至基板上。在旋塗期間,在包括如本文揭示的第一及第二聚合物兩者的光阻劑組合物中,光阻劑中的第一聚合物分離至所形成的光阻劑層的上表面,所述第一聚合物通常具有與上表面正下方區域中的第二聚合物的互混。可基於所利用的特定塗覆設備、溶液之黏度、塗覆工具之速度及允許旋轉之時間量來調節塗層溶液之固體含量以提供所需膜厚。光阻劑層之典型厚度為約500至3000 Å。
光阻劑層可接著經軟烘烤以使層中之溶劑含量降至最低,從而形成無黏性塗層且改良層與基板之黏附。軟烘烤可在加熱板上或在烘箱中進行,其中加熱板為典型的加熱板。例如,軟烘烤溫度及時間將視光阻劑之特定材料及厚度而定。典型的軟烘烤在約90至150℃之溫度下進行,且時間為約30至90秒。
面塗層組合物可根據已知程序來利用且塗覆在所施加的光阻劑上。關於可用於本發明面塗層組合物的使用面塗層組合物之程序,參見US20170090287。面塗層組合物宜用於浸沒式曝光方案之情況。
光阻劑層接著宜經由光遮罩暴露於活化輻射,以在曝光區域與未曝光區域之間產生溶解度差異。此處提及將光阻劑組合物暴露於對組合物起活化作用的輻射指示輻射能夠在光阻劑組合物中形成潛影。光遮罩具有對應於光阻劑層的區域的光學透明區域及光學不透明區域,以在隨後的顯影步驟中分別加以保留及移除。曝光波長通常為小於400 nm、小於300 nm或小於200 nm,其中典型的為248 nm、193 nm及EUV波長。光阻劑材料可進一步用於電子束曝光之情況。所述方法可用於浸沒式或乾式(非浸沒式)微影技術。曝光能量典型地為約10至80 mJ/cm2
,其視曝光工具及感光組合物之組分而定。
在光阻劑層曝光之後,進行曝光後烘烤(post-exposure bake,PEB)。PEB可例如在加熱板上或在烘箱中進行。PEB之條件將視例如特定的光阻劑組合物及層厚而定。PEB典型地在約80至150℃之溫度下進行,且時間為約30至90秒。在光阻劑中形成由極性切換區域與非切換區域(分別對應於曝光區域及未曝光區域)之間的邊界(虛線)限定的潛影。咸信在曝光後烘烤期間去保護的第一聚合物的鹼性部分(例如胺)防止光阻劑層的可能存在漫射光或散射光的暗區的極性切換,產生具有豎直壁的潛影。這係由PAG在暗區中產生的酸的中和的結果。因此,可實質上防止彼等區域中酸不穩定基團發生裂解。
接著宜使曝光的光阻劑層顯影以移除光阻劑層之未曝光區域。如所論述,顯影劑可為有機顯影劑,例如選自酮、酯、醚、烴及其混合物之溶劑。合適的酮溶劑包含例如丙酮、2-己酮、5-甲基-2-己酮、2-庚酮、4-庚酮、1-辛酮、2-辛酮、1-壬酮、2-壬酮、二異丁基酮、環己酮、甲基環己酮、苯基丙酮、甲基乙基酮及甲基異丁基酮。合適的酯溶劑包含例如乙酸甲酯、乙酸丁酯、乙酸乙酯、乙酸異丙酯、乙酸戊酯、丙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、二乙二醇單乙醚乙酸酯、3-乙氧基丙酸乙酯、乙酸3-甲氧基丁酯、乙酸3-甲基-3-甲氧基丁酯、甲酸甲酯、甲酸乙酯、甲酸丁酯、甲酸丙酯、乳酸乙酯、乳酸丁酯及乳酸丙酯。合適的醚溶劑包含例如二噁烷、四氫呋喃及二醇醚溶劑,例如,乙二醇單甲醚、丙二醇單甲醚、乙二醇單乙醚、丙二醇單乙醚、二乙二醇單甲醚、三乙二醇單乙醚及甲氧基甲基丁醇。合適的醯胺溶劑包含例如N-甲基-2-吡咯啶酮、N,N-二甲基乙醯胺及N,N-二甲基甲醯胺。合適的烴溶劑包含例如芳族烴溶劑,諸如甲苯及二甲苯。另外,可使用此等溶劑之混合物、或與除上文所述的彼等溶劑以外的溶劑混合或與水混合的所列溶劑中中一或多者。其他合適的溶劑包含用於光阻劑組合物中之彼等者。顯影劑較佳為2-庚酮或乙酸丁酯,諸如乙酸正丁酯。
有機溶劑之混合物可用作顯影劑,例如第一及第二有機溶劑之混合物。第一有機溶劑可選自羥烷基酯,諸如2-羥基異丁酸甲酯及乳酸乙酯;以及乙酸直鏈或分支鏈C5
至C6
烷氧基烷酯,諸如丙二醇單甲醚乙酸酯(PGMEA)。在第一有機溶劑中,較佳2-庚酮及5-甲基-2-己酮。第二有機溶劑可選自直鏈或分支鏈未取代之C6
至C8
烷基酯,諸如乙酸正丁酯、乙酸正戊酯、丙酸正丁酯、乙酸正己酯、丁酸正丁酯及丁酸異丁酯;以及直鏈或分支鏈C8
至C9
酮,諸如4-辛酮、2,5-二甲基-4-己酮及2,6-二甲基-4-庚酮。在第二有機溶劑中,較佳乙酸正丁酯、丙酸正丁酯及2,6-二甲基-4-庚酮。第一及第二有機溶劑之較佳組合包含2-庚酮/丙酸正丁酯、環己酮/丙酸正丁酯、PGMEA/丙酸正丁酯、5-甲基-2-己酮/丙酸正丁酯、2-庚酮/2,6-二甲基-4-庚酮及2-庚酮/乙酸正丁酯。其中,2-庚酮/乙酸正丁酯及2-庚酮/丙酸正丁酯尤其較佳。
按顯影劑之總重量計,有機溶劑通常以90重量%至100重量%,更通常大於95重量%、大於98重量%、大於99重量%或100重量%的組合量存在於顯影劑中。
顯影劑亦可為含水鹼性組合物,諸如TMAH組合物。含水鹼性顯影劑可商購獲得。
顯影劑材料可包含視情況選用之添加劑,例如,諸如上關於光阻劑所述的界面活性劑。按顯影劑之總重量計,此類視情況選用之添加劑通常將以較小的濃度,例如以約0.01至5重量%的量存在。
通常藉由旋塗將顯影劑施加至基板上。顯影時間為可有效移除光阻劑的未曝光區域的時段,其中典型的時間為5至30秒。顯影通常在室溫下進行。可進行顯影過程而無需在顯影後使用清洗漂洗。就此而言,已發現顯影過程可產生無殘餘物的晶圓表面,使得無需此類附加的漂洗步驟。
使用光阻劑圖案作為蝕刻遮罩,對BARC層(若存在)進行選擇性蝕刻,暴露下面的硬遮罩層。接著再次使用光阻劑圖案作為蝕刻遮罩,對硬遮罩層進行選擇性蝕刻,產生圖案化BARC及硬遮罩層。用於蝕刻BARC層及硬遮罩層的合適的蝕刻技術及化學物質在此項技術中已知,且將視例如此等層之特定材料而定。乾式蝕刻過程,諸如反應性離子蝕刻為典型的。接著使用已知技術,例如氧電漿灰化,自基板中移除光阻劑圖案及圖案化的BARC層。
以下非限制性實例說明本發明。 實例 分子量測定:
在以下實例中,在配備有折射率偵測器之Waters alliance System上藉由凝膠滲透層析法(gel permeation chromatography,GPC)量測聚合物之數量平均分子量及重量平均分子量Mn及Mw以及多分散性(PDI)值(Mw/Mn)。將樣品溶解於約1 mg/mL濃度之HPCL級THF中,且經由四個Shodex管柱(KF805、KF804、KF803及KF802)注入。維持1毫升/分鐘流速及35℃溫度。用窄分子量PS標準品(EasiCal PS-2,Polymer Laboratories, Inc.)校準所述管柱。 實例1至實例2:樹脂製備
藉由合併139.5 g丙二醇單甲醚乙酸酯(PGMEA)、150.0 g單體M1及30.0 g單體M2來製備單體進料溶液。藉由合併59.0 g PGMEA及4.45 g V-601製備引發劑進料溶液。攪拌混合物以溶解組分。將167.5 g PGMEA引入反應容器中且用氮氣吹掃容器30分鐘。接著在攪拌下將反應容器加熱至80℃。隨後將單體進料溶液引入反應容器中且經2小時的時段進料,且同時經3小時的時段將引發劑進料溶液進料至反應容器中。在攪拌下使反應容器在80℃下再維持七小時,且隨後使其冷卻至室溫。用500 mL四氫呋喃稀釋反應混合物,隨後藉由將反應混合物滴加至10 L 4/1甲醇/水(體積/體積)中使聚合物沈澱。藉由過濾收集固體聚合物,且在真空中乾燥。得到呈白色固體粉末狀之聚合物B1[產量:143 g,Mw = 34.3 kDa,PDI = 2.4]。 實例2:聚合物B2合成:
藉由合併89.1 g丙二醇單甲醚乙酸酯(PGMEA)、188.0 g單體M1及12.0 g單體M3來製備單體進料溶液。藉由合併80.9 g PGMEA及10.0 g V-601來製備引發劑進料溶液。攪拌混合物以溶解組分。將120.0 g PGMEA引入反應容器中且用氮氣吹掃容器30分鐘。接著在攪拌下將反應容器加熱至90℃。隨後將單體進料溶液引入反應容器中且經2小時的時段進料,且同時經3小時的時段將引發劑進料溶液進料至反應容器中。在攪拌下使反應容器在90℃下再維持七小時,且隨後使其冷卻至室溫。用500 mL四氫呋喃稀釋反應混合物,隨後藉由將反應混合物滴加至10 L 4/1甲醇/水(體積/體積)中使聚合物沈澱。藉由過濾收集固體聚合物,且在真空中乾燥。得到呈白色固體粉末狀之聚合物B2[產量:170 g,Mw = 10.3 kDa,PDI = 2.2]。 實例3:光阻劑組合物製備 光阻劑組分:
藉由以表1中所述的量,將上述組分添加至包括按重量計1/1的丙二醇單甲醚乙酸酯(PGMEA)及2-羥基丁酸甲酯(HBM)的溶劑體系中來調配光阻劑組合物。使各混合物過濾通過0.2 μm PTFE盤。 表1. 實例及比較光阻劑組合物.
CR =比較實例;S1 = 1/1 PGMEA/HBM。 實例4:光阻劑評估NMR 實驗:
將光阻劑組合物在35℃下儲存指定的時間,隨後用d6
-丙酮稀釋一半,且收集19
F NMR光譜以測定含氟聚合物B之降解百分比。此藉由比較對應於聚合物的氟峰(fluorine peak)及對應於降解產物的氟峰的積分來完成。在26℃下在具有5 mm SMARTProbeTM
之Bruker AVANCE III HD 600 MHz光譜儀上獲得19
FNMR光譜。使用MestReNova 6.2.1處理所有NMR光譜。將來自分析之資料彙總於表2。 表2.來自實例及比較光阻劑組合物之NMR分析的降解資料. 儲存壽命穩定性實驗:
將光阻劑組合物在35℃下儲存指定的時間,隨後測試其後退接觸角及微影效能。後退接觸角( RCA )量測:
在TEL ACT-8 track上,在120℃下用六甲基二矽氮烷(HMDS)對200 mm矽晶圓進行底塗持續30秒。使用85℃的軟烘烤將光阻劑組合物塗覆至1,000 Å之厚度持續60秒。使用Kruss接觸角測角儀使用去離子的密理博(Millipore)過濾水量測後退水接觸角。對於後退接觸角量測,DI水之液滴大小為50 μl,且晶圓台傾斜速率為1度/秒。微影處理:
如下藉由微影評估光阻劑組合物。200 mm晶圓首先經XU080538AA底層旋塗且在240℃下烘烤60秒以形成135 nm膜。隨後將SiARC旋塗在頂部且在240℃下烘烤60秒以形成22 nm膜。最後,將光阻劑組合物旋塗在頂部以形成100 nm之膜且在85℃下軟烘烤60秒。隨後在習知照射下使用ArF曝光裝置ASML-1100,NA = 0.75,經由具有緻密空間的遮罩圖案,用ArF準分子雷射器(193 nm)對塗覆的晶圓進行曝光。此後,將晶圓在95℃下烘烤60秒,接著用0.26N四甲基氫氧化銨(TMAH)水溶液顯影,且隨後用水洗滌。藉由使用日立(Hitachi)9380 CD-SEM,在800伏特(V)加速電壓、8.0微微安(pA)探針電流下操作,使用200 K×放大率對所捕捉的影像進行自上向下的掃描電子顯微鏡術(scanning electron microscopy,SEM)處理來測定臨界尺寸(CD)。利用100 nm及200 nm間距的遮罩CD靶向100 nm緻密溝槽。針對CD測定對63個位點進行平均化。 表3. 實例及比較光阻劑組合物之效能資料.
實例5:面塗層組合物
藉由混合下列組分:IBIB中之5.14 g聚合物-B溶液(20%),IBIB中之2.21 g淬滅劑-A(Quencher-A)溶液(1%)及92.7 g IBIB,且隨後用0.2微米耐綸(Nylon)過濾器過濾此混合物來製備本發明之外塗層或面塗層組合物。 實例6:浸沒式微影
用ARTM26N(羅門哈斯電子材料)旋塗300 mm HMDS底塗之矽晶圓,以在TEL CLEAN TRACLITHIUSi+上形成第一底部抗反射塗層(bottom anti-reflective coating,BARC),接著在205℃下烘烤處理60秒。
在BARC層上旋塗實例3之光阻劑組合物(光阻劑R2)之塗層。將實例5之面塗層組合物旋塗至具有實例3之光阻劑組合物(光阻劑R2)塗層的矽晶圓上。
隨後使用如下照射條件經由尼康(Nikon)S306CArF浸沒式掃描儀上的遮罩曝光所製造之膜:1.3 NA,具有XY偏振之環形,δ0.64-0.8。曝光劑量i在23.0 mJ/cm2
至47.0 mJ/cm2
之間按1 mJ/cm2
變化。隨後將曝光之膜在90℃下曝光後烘烤60秒,接著用0.26N TMAH含水顯影劑進行顯影。
Claims (9)
- 如申請專利範圍第1項所述的光阻劑組合物,其進一步包括不同於所述第一聚合物之50至95重量%的第二聚合物。
- 如申請專利範圍第2項所述的光阻劑組合物,其中所述第二聚合物為氟化聚合物。
- 如申請專利範圍第5項所述的面塗層組合物,其中所述第二聚合物為氟化聚合物。
- 一種形成光微影圖案之方法,其包括:(a)在基板上施加一層如申請專利範圍第1項至第4項中任一項所述的光阻劑組合物;(b)以圖案方式將所述光阻劑組合物層暴露於活化輻射;及(c)使曝光之所述光阻劑組合物層顯影,以得到光阻劑凸紋影像。
- 一種處理光阻劑組合物之方法,其包括:(a)在基板上施加一層光阻劑組合物;(b)在所述光阻劑組合物層之上方,施加一層如申請專利範圍第5項至第7項中任一項所述的組合物,以形成面塗層;(c)以圖案方式將所述面塗層及光阻劑層暴露於活化輻射;及(d)使曝光之所述光阻劑組合物層顯影,以得到光阻劑凸紋影像。
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