TWI751336B - 用於化學增幅抗蝕劑組成物之含碘聚合物 - Google Patents
用於化學增幅抗蝕劑組成物之含碘聚合物 Download PDFInfo
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- TWI751336B TWI751336B TW107116738A TW107116738A TWI751336B TW I751336 B TWI751336 B TW I751336B TW 107116738 A TW107116738 A TW 107116738A TW 107116738 A TW107116738 A TW 107116738A TW I751336 B TWI751336 B TW I751336B
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- 125000002950 monocyclic group Chemical group 0.000 claims description 18
- 125000003367 polycyclic group Chemical group 0.000 claims description 17
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
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- 230000000052 comparative effect Effects 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
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- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 5
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- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000008027 tertiary esters Chemical group 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
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Abstract
一種單體,具有式(I):
Description
本發明大體上係關於包含光酸產生劑之聚合物組成物。特定言之,本發明提供來源於含碘單體之共聚物。
極紫外光微影技術(「EUVL」)為替代光學光微影技術之主要技術選擇之一,以用於特徵尺寸<20 nm之體積半導體製造。極短之波長(13.4 nm)為多代技術所需高解析度之關鍵促進因素。此外,整個系統概念-掃描曝光、投影光學、掩模格式及抗蝕技術-與當前光學技術所使用非常相似。與前幾代光微影一樣,EUVL由抗蝕技術、曝光工具技術及掩膜技術組成。主要挑戰為EUV源功率及吞吐量。EUV電源之任何改進皆將直接影響目前嚴格的抗蝕劑敏感度規格。事實上,EUVL顯影中之一個主要問題為抗蝕劑敏感度,敏感度越低,所需源功率越大或者需要使抗蝕劑完全曝光之曝光時間越長。功率水平越低,噪音對印刷線之線邊緣粗糙度(「LER」)影響越大。
提高極紫外(「EUV」)之敏感度為關鍵促進因素。已證實,EUV光吸收截面及二次電子產生率為EUV敏感度之關鍵因素。一種增加EUV光致抗蝕劑敏感度之方法為增加其在13.5 nm下之吸收截面,所述吸收截面為可使用已知原子吸收在理論上計算之材料之原子特性。構成抗蝕劑材料之典型原子(如碳、氧、氫及氮)在13.5 nm下具有非常弱的吸收。氟原子之吸收稍高,且已用於尋找高EUV吸收光致抗蝕劑。
碘在EUV輻射下具有非常高的吸收截面。最近專利申請案JP 2015-161823揭示可用於光微影加工之含碘單體及相應聚合物。然而,此等單體皆未考慮延伸鏈來改良含碘單體之結合。仍需要富含碘之單體及相應聚合物,其具有良好的溶解性且在EUV曝光下賦予改良之敏感度。
一個實施例提供具有式(I)之單體:(I) 其中在式(I)中: W為-(C=O)O-、-O(C=O)-、-O(SO2
)-、-(SO2
)O-、-NH(SO2
)-、-(SO2
)NH-、-NH(CO)-、-(CO)NH-、-SO2
-、-SO-, Ra
為H、F、-CN、C1-10
烷基或C1-10
氟烷基; L為選自以下之連接基團:未經取代或經取代之C1-20
伸烷基、未經取代或經取代之C3-20
伸環烷基、未經取代或經取代之C6-20
伸芳基及未經取代或經取代之C7-20
伸芳烷基;表示單環或多環未經取代或經取代之C6-30伸芳基或單環或多環未經取代或經取代之C3-30伸雜芳基,其中「*」表示與相鄰基團或原子之連接點;「I」表示碘;X選自-F、-Cl、-Br、羥基、氰基、硝基、胺基、脒基、肼基、腙基、羧酸基或其鹽、磺酸基或其鹽、磷酸基或其鹽、未經取代或經取代之C1-30烷基、未經取代或經取代之C2-30烯基、未經取代或經取代之C2-30炔基、未經取代或經取代之C1-30烷氧基、未經取代或經取代之C3-30環烷基、未經取代或經取代之C1-30雜環烷基、未經取代或經取代之C3-30環烯基、未經取代或經取代之C1-30雜環烯基、未經取代或經取代之C6-30芳基、未經取代或經取代之C6-30芳氧基、未經取代或經取代之C6-30芳硫基、未經取代或經取代之C7-30芳烷基、未經取代或經取代之C1-30雜芳基、未經取代或經取代之C2-30雜芳氧基、未經取代或經取代之C2-30雜芳硫基或未經取代或經取代之C3-30雜芳烷基,其中X視情況包含酯基或-C(CF3)2OH;m為0或更大之整數,其限制條件為當m為2或更大之整數時,兩個相鄰之基團X視情況形成環;且n為1或更大之整數。
另一實施例提供包含上述單體及酸可脫保護單體之聚合產物之共聚物。
另一實施例提供包含上述聚合物之光致抗蝕劑組成物及包含光致抗蝕劑組成物層之塗覆基板。
另一實施例提供一種形成電子裝置之方法,包含:(a)在基板表面上塗覆根據技術方案11至13中任一項之光致抗蝕劑組成物之層; (b)將光致抗蝕劑組成物層逐圖案地暴露於活化輻射;及 (c)使暴露之光致抗蝕劑組成物層顯影,以提供抗蝕劑凸紋影像。
現將詳細參考例示性實施例,其實例在附圖中示出,其中相同附圖標記始終指相同元件。就此而言,本發明之例示性實施例可具有不同形式,且不應解釋為限於本文闡述之說明。因此,以下僅藉由參考附圖來描述例示性實施例,以解釋本說明書之各個態樣。如本文所使用,術語「及/或」包含一或多個相關所列項目中之任一個及所有組合。如「……中之至少一者」之表述當在元件列表之前時修飾元件之整個列表而不修飾列表之個別元件。
將理解,當元件稱為在另一元件「上」時,其可直接與其他元件接觸或其間可存在中間元件。相比之下,當元件稱為「直接在另一元件上」時,不存在插入元件。
將理解,儘管本文中可使用術語第一、第二、第三等來描述各種元件、組件、區域、層及/或部分,但此等元件、組件、區域、層及/或部分不應受此等術語限制。此等術語僅用以區分一個元件、組件、區域、層或部分與另一個元件、組件、區域、層、部分或部分。因此,在不偏離本發明實施例之教示內容之情況下,下文所論述之第一元件、組件、區域、層或部分可稱為第二元件、組件、區域、層或部分。
本文中所使用之術語僅出於描述特定實施例之目的,且不意欲為限制性。如本文中所使用,除非上下文另外清楚地指示,否則單數形式「一(a/an)」及「所述」意欲亦包含複數形式。
將進一步理解,術語「包括(comprises/comprising)」或「包含(includes/including)」當用於本說明書中時,指定所陳述特徵、區域、整數、步驟、操作、元件及/或組件之存在,但不排除一或多個其他特徵、區域、整數、步驟、操作、元件、組件及/或其群組之存在或添加。
如本文所使用,「約」或「大致」包含所述值且意謂在偏差之可接受範圍內,對於特定值,如由一般熟習此項技術者所確定,考慮相關量測及與特定數量之量測相關之誤差(即量測系統之侷限性)。舉例而言,「約」可意謂在一或多種標準差內,或在所述值之± 30%、20%、10%、5%內。
除非另外定義,否則本文所用之所有術語(包含技術及科學術語)具有與熟習本發明一般熟習此項技術者通常理解之相同含義。將進一步理解,術語(如在常用詞典中所定義之術語)應解釋為具有與其在相關技術及本發明之上下文中之含義一致之含義,且除非本文中明確地定義,否則將不會以理想化或過分正式意義進行解釋。
如本文中所使用,當未另外提供定義時,術語「烷基」指來源於具有指定碳原子數目且具有至少一種價態之直鏈或分支鏈飽和脂族烴之基團。
如本文中所使用,當未另外提供定義時,術語「氟烷基」指一或多個氫原子經氟原子置換之烷基。
如本文中所使用,當未另外提供定義時,術語「烷氧基」指「烷基-O-」,其中術語「烷基」具有與上文所描述之含義相同之含義。
如本文中所使用,當未另外提供定義時,術語「氟烷氧基」指一或多個氫原子經氟原子置換之烷氧基。
如本文中所使用,當未另外提供定義時,術語「環烷基」指具有一或多個飽和環(其中所有環成員為碳)之單價基團。
如本文所用,當未另外提供定義時,術語「烯基」指具有至少一個碳-碳雙鍵之直鏈或分支鏈之一價烴基。
如本文所用,當未另外提供定義時,術語「鏈烯基烷基」指「鏈烯基-烷基-」,其中術語「鏈烯基」及「烷基」具有與上述相同之含義。
如本文所用,當未另外提供定義時,術語「炔基」指具有至少一個碳-碳參鍵之直鏈或分支鏈,一價烴基。
如本文所用,當未另外提供定義時,術語「炔基烷基」指「炔基-烷基-」,其中術語「炔基」及「烷基」具有與上述相同之含義。
如本文中所使用,當未另外提供定義時,單獨或以組合形式使用之術語「芳基」指含有至少一個環且具有規定碳原子數目的芳族烴或雜芳族烴。術語「芳基」可解釋為包含具有稠合至至少一個環烷基環或雜環烷基環之芳環或雜芳環之基團。「芳基」基團可包含一或多個獨立地選自氮(N)、氧(O)、P(磷)及硫(S)之雜原子。
如本文中所使用,當未另外提供定義時,術語「芳氧基」指「芳基-O-」,其中術語「芳基」具有與上文所描述之含義相同之含義。
如本文中所使用,當未另外提供定義時,術語「芳烷基」指共價連接至烷基(連接至化合物)之經取代或未經取代之芳基。
如本文中所使用,當未另外提供定義時,術語「伸烷基」指直鏈或分支鏈飽和脂族烴基,其具有至少兩種價態,視情況經一或多個所指示取代基取代,其限制條件為不超過伸烷基之價態。
如本文中所使用,當未另外提供定義時,術語「伸環烷基」指環烴基,其具有至少兩種價態,視情況經一或多個所指示取代基取代,其限制條件為不超過伸環烷基之價態。
如本文中所使用,當未另外提供定義時,術語「伸芳基」指官能基,其具有至少兩種價態,藉由移除芳環中之兩個氫得到,視情況經一或多個所指示取代基取代,其限制條件為不超過伸芳基之價態。
如本文中所使用,當未另外提供定義時,術語「伸芳烷基」指官能基,其具有至少兩種價態,藉由自經烷基取代之芳族化合物中移除兩個氫得到,視情況經一或多個所指示取代基取代,其限制條件為不超過伸芳烷基之價態。
如本文中所使用,當未另外提供定義時,術語「伸雜芳基」指官能基,其具有至少兩種價態,藉由移除雜芳環中之兩個氫得到,視情況經一或多個所指示取代基取代,其限制條件為不超過伸雜芳基之價態。
如上所述,提高EUV光微影技術敏感度之一種方法為增大抗蝕劑組成物在13.5 nm下之吸收截面。在EUV波長下增強化學增幅抗蝕劑吸收需要結合高度吸收元素。在元素之EUV下之原子吸收截面在文獻中為已知的(參見例如:Fallica R.等人《SPIE先進光微影技術(SPIE Advanced Lithography)》,977612, 2016)以及其中引用之參考文獻)。用於有機化學增幅抗蝕劑之分子及聚合物之元素組成主要限於碳、氫、氧及氮。此等元素在13.5 nm下之吸收極低。與氧原子相比,氟原子在13.5 nm下之吸收稍高。Christianson等人探索將氟原子結合至聚合物主鏈(參見Christianson等人,《SPIE先進光微影技術》 868216, 2013)。碘原子在EUV下具有顯著更高之吸收截面。本申請案之發明人發現含碘樹脂及相應之抗蝕劑組成物,其在EUV下具有改良之光致抗蝕劑敏感度。藉由將碘原子結合至抗蝕劑樹脂來實現敏感度之提高,而含碘單體之延伸鏈改良其在樹脂中之結合。
在式(I)中:W為-(C=O)O-、-O(C=O)-、-O(SO2)-、-(SO2)O-、-NH(SO2)-、-(SO2)NH-、-NH(CO)-、-(CO)NH-、-SO2-、-SO-,Ra可為H、F、-CN、C1-10烷基或C1-10氟烷基;L可為選自未經取代或經取代之C1-20伸烷基,未經取代或經取代之C3-20伸環烷基,未經取代或經取代之C6-20伸芳基及未經取代或經取代之C7-20伸芳烷基之連接基團;
表示單環或多環未經取代或經取代之C6-30伸芳基或單環或多環未經取代或經取代之C3-30伸雜芳基,其中「*」表示與相鄰基團或原子之連接點;「I」表示碘;X可選自-F,-Cl,-Br,羥基,氰基,硝基,胺基,脒基,肼基,腙基,羧酸基或其鹽,磺酸基或其鹽,磷酸基或其鹽,未經取代或經取代之C1-30烷基,未經取代或經取代之C2-30
烯基,未經取代或經取代之C2-30
炔基,未經取代或經取代之C1-30
烷氧基,未經取代或經取代之C3-30
環烷基,未經取代或經取代之C1-30
雜環烷基,未經取代或經取代之C3-30
環烯基,未經取代或經取代之C1-30
雜環烯基,未經取代或經取代之C6-30
芳基,未經取代或經取代之C6-30
芳氧基,未經取代或經取代之C6-30
芳硫基,未經取代或經取代之C7-30
芳基烷基,未經取代或經取代之C1-30
雜芳基,未經取代或經取代之C2-30
雜芳基氧基,未經取代或經取代之C2-30
雜芳基硫基或未經取代或經取代之C3-30
雜芳基烷基, 其中X視情況包含酯基或-C(CF3
)2
OH; m可為0或更大之整數,其限制條件為當m為2或更大之整數時,兩個相鄰之基團X可視情況形成環;且 n可為1或更大之整數。
在上述單體中,C6-30
伸芳基可為單環C6-30
伸芳基、稠合雙環C6-30
伸芳基或單鍵鍵結之C6-30
伸芳基。C6-30
伸芳基可為1,2-伸苯基,例如1,2-伸苯基、1,3-伸苯基及1,4-伸苯基。稠合之雙環C6-30
伸芳基可為經雙取代之萘基、經雙取代之蒽基或經雙取代之菲基。單鍵鍵結之C6-30
伸芳基可為經雙取代之伸聯苯基或經雙取代之伸三聯苯基。C3-30
伸雜芳基可為單環C3-30
伸雜芳基、稠合雙環C3-30
伸雜芳基或單鍵鍵結之C3-30
伸雜芳基。
連接基團L可為未經取代之C1-20
伸烷基或經-F取代之C1-20
伸烷基、羥基或C1-10
烷基。
在一個實施例中,X可為羥基。X亦可為未經取代或經取代之C1-30
烷基、未經取代或經取代之C2-30
烯基、未經取代或經取代之C2-30
炔基、未經取代或經取代之C1-30
烷氧基、未經取代或經取代之C3-30
環烷基、未經取代或經取代之C1-30
雜環烷基、未經取代或經取代之C3-30
環烯基、未經取代或經取代之C1-30
雜環烯基、未經取代或經取代之C6-30
芳基、未經取代或經取代之C6-30
芳氧基、未經取代或經取代之C6-30
芳硫基、未經取代或經取代之C7-30
芳烷基、未經取代或經取代之C1-30
雜芳基、未經取代或經取代之C2-30
雜芳氧基、未經取代或經取代之C2-30
雜芳硫基或未經取代或經取代之C3-30
雜芳烷基。此等基團中之每一個可視情況包含酸可裂解基團,如第三酯基或縮醛基。
另外,在式(I)中,變數m表示連接至三價基團之取代基X之數目。取代基X之數目可以視此基團之性質而變,且可為1或更大之整數,例如1、2、3、4、5、6、7、8或9。在一個實施例中,m可為1、2或3。當m為2或更大之整數時,兩個相鄰之基團X可視情況形成環。
在式(II)中,Rb
可獨立地為H、未經取代或經取代之C1-20
烷基、未經取代或經取代之C3-20
環烷基、未經取代或經取代之C6-20
芳基或未經取代或經取代之C7-20
芳烷基,且每個Rb
可為分開的,或者至少一個Rb
可與相鄰Rb
鍵結以形成環狀結構。在一個實施例中,式(IV)中包含Rb
之第三基團可為第三丁基。在另一個實施例中,式(IV)可包含環烷基結構,其結合兩個或更多個Rb
基團,如1-甲基環戊基、1-乙基環戊基及1-甲基環己基及其類似基團。
聚合產物亦可包含來源於鹼溶性單體、含內酯之單體或其組合之重複單元。
在式(III)中,Q1
可為選自以下之含酯或不含酯基團:未經取代或經取代之C1-20
烷基、未經取代或經取代之C3-20
環烷基、未經取代或經取代之C6-20
芳基及未經取代或經取代之C7-20
芳烷基。在一個實施例中,當包含酯時,酯在Q1
與雙鍵之連接點之間形成連接鍵。以此方式,當Q1
為酯基時,式(III)可為(甲基)丙烯酸酯單體。在另一個實施例中,當不包含酯時,Q1
可為芳族的,從而使得式(III)可為例如苯乙烯類單體或乙烯基萘甲酸單體。Q1
可經氟化或未經氟化。此外,在式(III)中,a可為1至3之整數,例如,a可為1或2。
同樣在式(III)中,W可為包括選自以下中之至少一者之鹼反應性基團:-C(=O)-OH;-C(CF3
)2
OH;NH-SO2
-Y1
,其中Y1
可為F或C1-4
全氟烷基;-OH;以及任何前述物質與乙烯基醚之加合物。在一個實施例中,當Q為非芳族時(例如,當式(II)包含具有酯連接之烷基或環烷基Q之(甲基)丙烯酸酯結構時),W可為-C(CF3
)2
OH。在另一實施例中,當Q為芳族時(例如,當Q為酯連接之或非酯連接之且為芳族基團(如苯基或萘基)時),W可為OH或-C(CF3
)2
OH。預期任何鹼反應性基團可進一步受酸可分解縮醛離去基團(例如,具有通式結構-O-CH(R')-O-R」,其中R'可為甲基、乙基或其他烷基)保護。此類基團為乙烯基醚(例如乙基乙烯基醚、丙基乙烯基醚、第三丁基乙烯基醚、環己基乙烯基醚、1-金剛烷羧酸之2-乙烯氧基乙基酯、2-萘甲醯基乙基乙烯基醚或其他此類乙烯基醚)之加合物。
在式(IV)中,L可為單環、多環或稠合多環C4-20
含內酯基團。可包含此類內酯基團以不僅改良聚合物對基板之黏著性,且調節聚合物在鹼顯影劑中之溶解。在一個實施例中,L可為經由單環碳連接至(甲基)丙烯酸酯部分之單環C4-6
內酯;或L可為基於降莰烷型結構之C6-10
稠合多環內酯。
應瞭解,在式(IVa)中,R可為分開的或可連接至內酯環及/或一或多個R基團,且甲基丙烯酸脂部分可直接或經由R間接連接至內酯環。
在式(VI)中, X可為S或I, 各Rc
可經鹵代或未經鹵代,且獨立地為C1-30
烷基;多環或單環C3-30
環烷基;多環或單環C4-30
芳基, 其中當X為S時,一個Rc
基團視情況藉由單鍵連接至一個相鄰Rc
基團,且z為2或3,且 其中當X為I時,z為2,或當X為S時,z為3。
其中X為I或S,Rh、Ri、Rj及Rk未經取代或經取代,且各自獨立地為羥基、腈、鹵素、C1-30烷基、C1-30氟烷基、C3-30環烷基、C1-30氟環烷基、C1-30烷氧基、C3-30烷氧基羰基烷基、C3-30烷氧基羰基烷氧基、C3-30環烷氧基、C5-30環烷氧基羰基烷基、C5-30環烷氧基羰基烷氧基、C1-30氟烷氧基、C3-30氟烷氧基羰基烷基、C3-30氟烷氧基羰基烷氧基、C3-30氟環烷氧基、C5-30氟環烷氧基羰基烷基、C5-30氟環烷氧基羰基烷氧基、C6-30芳基、C6-30氟芳基、C6-30芳氧基或C6-30氟芳氧基,其各自未經取代或經取代;Rc如上所定義;Ar1及Ar2獨立地為C10-30稠合或單鍵鍵結之多環芳基;p為2或3之整數;其中當X為I時,p為2,且其中當X為S時,p為3,q及r各自獨立地為0至5之整數,u為0至1之整數,其中當u為0時,X為I,且其中當u為1時,X為S,且s及t各自獨立地為0至4之整數。
在式(VII)、(VIII)或(IX)中,Rh、Ri、Rj及Rk中之至少一個可為酸可裂解基團。在一個實施例中、酸可裂解基團可為(i)第三C1-30
烷氧基(例如第三丁氧基)、第三C3-30
環烷氧基、第三C1-30
氟烷氧基,(ii)第三C3-30
烷氧基羰基烷基、第三C5-30
環烷氧基羰基烷基、第三C3-30
氟烷氧基羰基烷基,(iii)第三C3-30
烷氧基羰基烷氧基、第三C5-30
環烷氧基羰基烷氧基、第三C3-30
氟烷氧基羰基烷氧基,或(iv)包含-O-C(R11
R12
)-O-部分之C2-30
縮醛基(其中R11
R12
各自獨立地為氫或C1-30
烷基)。
包含本文揭示之共聚物及不可聚合之光酸產生劑之光致抗蝕劑組成物可用於提供包含光致抗蝕劑之層。經塗佈之基板可由光致抗蝕劑組成物形成。此類經塗佈之基板包含:(a)在其表面上具有一或多個待圖案化之層之基板;及(b)在一或多個待圖案化之層上方之光致抗蝕劑組成物之層。
基板可為任何尺寸及形狀,且較佳為適用於光微影之基板,如矽、二氧化矽、絕緣體上矽(silicon-on-insulator,SOI)、應變矽、砷化鎵;經塗佈之基板,包含用氮化矽、氮氧化矽、氮化鈦、氮化鉭塗佈之基板;超薄柵極氧化物,如氧化鉿;金屬或經金屬塗佈之基板,包含用鈦、鉭、銅、鋁、鎢、其合金塗佈之基板;以及其組合。較佳地,本文中之基板表面包含待圖案化之臨界尺寸層,包含例如一或多個柵極層或基板上用於半導體製造之其他臨界尺寸層。此類基板較佳可包含矽、SOI、應變矽及其他此類基板材料,形成為具有例如20 cm、30 cm或更大直徑之尺寸或適用於晶片製造生產之其他尺寸之圓形晶片。
另外,一種形成電子裝置之方法包含(a)將以上光致抗蝕劑組成物層塗覆(鑄造)於基板表面上;(b)將光致抗蝕劑組成物層逐圖案地暴露於活化輻射;及(c)使暴露之光致抗蝕劑組成物層顯影,從而得到抗蝕劑凸紋影像。
塗覆可藉由任何適合的方法來實現,包含旋塗、噴塗、浸塗、刀片刮抹或其類似方法。塗覆光致抗蝕劑層較佳藉由使用塗佈軌旋塗含光致抗蝕劑之溶劑來實現,其中光致抗蝕劑施配於旋轉晶片上。在施配期間,晶片可以高達4,000 rpm,較佳約200至3,000 rpm且更佳1,000至2,500 rpm之速度旋轉。旋轉所塗佈之晶圓以移除溶劑,且在加熱板上烘烤以自膜中移除殘餘溶劑及自由體積來使其密度均勻。
鑄造溶劑可為一般熟習此項技術者已知之任何適合的溶劑。舉例而言,鑄造溶劑可為脂族烴(如己烷、庚烷及其類似物)、芳族烴(如甲苯、茬及其類似物)、鹵代烴(如二氯甲烷、1,2-二氯乙烷、1-氯己烷及其類似物)、醇(如甲醇、乙醇、1-丙醇、異丙醇、第三丁醇、2-甲基-2-丁醇、4-甲基-2-戊醇及其類似物)、水、醚(如乙醚、四氫呋喃、1,4-二噁烷、茴香醚及其類似物)、酮(如丙酮、甲基乙基酮、甲基異丁基酮、2-庚酮、環己酮及其類似物)、酯(如乙酸乙酯、乙酸正丁酯、丙二醇單甲基醚乙酸酯(「PGMEA」)、乳酸乙酯、乙醯乙酸乙酯及其類似物)、內酯(如 -丁內酯、 -己內酯及其類似物)、腈(如乙腈、丙腈及其類似物)、非質子雙極性溶劑(如二甲伸碸、二甲基甲醯胺及其類似物),或其組合。鑄造溶劑之選擇取決於特定光致抗蝕劑組成物且可以由一般熟習此項技術者基於知識及經驗來容易地進行。
接著使用曝光工具(例如步進器)來進行逐圖案曝光,其中膜經由圖案遮罩照射且藉此逐圖案曝光。所述方法較佳使用先進曝光工具,其在能夠具有高解析度之波長(包含EUV或電子束輻射)下產生活化輻射。應瞭解,使用活化輻射之曝光在曝光區中分解PAG,且產生酸及分解副產物,且隨後酸或副產物實現聚合物及奈米粒子中之化學變化(使酸敏性基團去阻斷來產生鹼溶性基團,或替代地催化在曝光區中之交聯反應)。此類曝光工具之解析度可小於30 nm。
隨後,曝光之光致抗蝕劑層之顯影藉由用能夠選擇性地移除曝光膜部分(其中光致抗蝕劑為正型)或移除未曝光膜部分(其中光致抗蝕劑在曝光區域中可交聯,亦即,為負型)之合適顯影劑處理曝光層來實現。較佳地,光致抗蝕劑為負型,基於具有側接及/或游離之酸基團或副產物之聚合物(來源於照射後之結合或游離PAG)抑制奈米粒子之溶解,且顯影劑較佳為基於溶劑的。藉由顯影形成圖案。溶劑顯影劑可為此項技術中已知之任何適合的顯影劑。舉例而言,溶劑顯影劑可為脂族烴(如己烷、庚烷及其類似物)、芳族烴(如甲苯、茬及其類似物)、鹵代烴(如二氯甲烷、1,2-二氯乙烷、1-氯己烷及其類似物)、醇(如甲醇、乙醇、1-丙醇、異丙醇、第三丁醇、2-甲基-2-丁醇、4-甲基-2-戊醇及其類似物)、水、醚(如乙醚、四氫呋喃、1,4-二噁烷、茴香醚及其類似物)、酮(如丙酮、甲基乙基酮、甲基異丁基酮、2-庚酮、環己酮及其類似物)、酯(如乙酸乙酯、乙酸正丁酯、丙二醇單甲基醚乙酸酯(「PGMEA」)、乳酸乙酯、乙醯乙酸乙酯及其類似物)、內酯(如 -丁內酯、 -己內酯及其類似物)、腈(如乙腈、丙腈及其類似物)、非質子雙極性溶劑(如二甲伸碸、二甲基甲醯胺及其類似物),或其組合。在一個實施例中,溶劑顯影劑可為溶劑之可混溶混合物,例如醇(異丙醇)與酮(丙酮)之混合物。顯影劑溶劑之選擇取決於特定光致抗蝕劑組成物,且可以由一般熟習此項技術者基於知識及經驗容易地進行。
當用於一或多種此類圖案形成方法中時,光致抗蝕劑可用於製造電子及光電子裝置,如記憶體裝置、處理器晶片(CPU)、圖形晶片以及其他此類裝置。
聚合產物可進一步包含來源於包括光酸產生劑之單體之重複單元。
在式(V)中,各Ra
可獨立地為H、F、C1-10
烷基或C1-10
氟烷基。如本說明書通篇所使用,「氟」或「氟化」意指一或多個氟基團連接至關聯基團。舉例而言,藉由此定義且除非另外規定,否則「氟烷基」涵蓋單氟烷基、二氟烷基及其類似基團,以及烷基之基本上所有碳原子經氟原子取代之全氟烷基;類似地,「氟芳基」意指單氟芳基、全氟芳基及其類似基團。在此情形中,「基本上所有」意指大於或等於90%,較佳大於或等於95%且更佳大於或等於98%之所有連接至碳的原子為氟原子。
在式(V)中,Q2
為單鍵或含酯或不含酯之氟化或未氟化基團,其選自C1-20
烷基、C3-20
環烷基、C6-20
芳基及C7-20
芳烷基。舉例而言,當包含酯時,酯可在Q2
與雙鍵之連接點之間形成連接鍵。以此方式,當Q2
為酯基時,式(V)可為(甲基)丙烯酸酯單體。當不包含酯時,Q2
可為芳族的,從而使得式(V)可為例如苯乙烯類單體或乙烯基萘甲酸單體。
同樣,在式(V)中,A為選自C1-20
烷基、C3-20
環烷基、C6-20
芳基或C7-20
芳烷基之含酯或不含酯、氟化或未氟化之基團。適用的A基團可包含氟化之芳族部分、直鏈氟烷基或分支鏈氟烷基酯。舉例而言,A可為-[(C(Re
)2
)x
(=O)O]c
-(C(Rf
)2
)y
(CF2
)z
-基團,或經鄰、間或對取代之-C6
Rg 4
-基團,其中各Re
、Rf
及Rg
各自獨立地為H、F、C1-6
氟烷基或C1-6
烷基,c可為0或1,x可為1至10之整數,y及z可獨立地為0至10之整數,且y+z之總和可至少為1。
同樣,在式(V)中,Z-
可為包含磺酸根(-SO3 -
)之陰離子基團、磺醯胺(-SO2
(N-
)R'之陰離子,其中R'可為C1-10
烷基或C6-20
芳基,或磺醯亞胺之陰離子。當Z-
為磺醯亞胺時,磺醯亞胺可為具有通式結構A-SO2
-(N-
)-SO2
-Y2
之不對稱磺醯亞胺,其中A如上文所描述,且Y2
為直鏈或分支鏈C1-10
氟烷基。舉例而言,Y2
基團可為C1-4
全氟烷基,其可來源於相應全氟烷磺酸,如三氟甲磺酸或全氟丁磺酸。
另一實施例提供包含以上共聚物及經塗佈之基板之光致抗蝕劑組成物,所述經塗佈之基板包含:(a)在其表面上具有一或多個待圖案化之層之基板;及(b)在一或多個待圖案化之層上方之上述光致抗蝕劑組成物之層。
另一實施例提供一種形成電子裝置之方法,包含: (a)在基板表面上塗覆上述光致抗蝕劑組成物之層; (b)將所述光致抗蝕劑組成物層逐圖案地暴露於活化輻射;及 (c)使所述暴露之光致抗蝕劑組成物層顯影,以提供抗蝕劑凸紋影像。
在下文中,參考實例更詳細地說明本發明。然而,此等實例為例示性,且本發明不限於此。 實例
此等實例中使用之單體之首字母縮略詞及化學結構列於表1中。根據文獻程序(《生物大分子(Biomacromolecules
)》, 4(3), 793-798;2003)製備TIPEMA單體。PPMA單體購自ENF Co., Ltd.,且DiHFA單體購自Central Glass Co., Ltd.。單體ECPPDBT ADMA-TFPS之合成描述於2016年4月18日提交之美國專利申請案第15/131,135號。 表
共聚物合成
此實例描述三種本發明之共聚物及一種比較共聚物之合成。表2彙總每種聚合物合成中使用之單體及相應之莫耳比。
共聚物1由單體PPMA、α-GBLMA、TIPEMA以39/49/12之莫耳進料比製備。藉由在16.38 g茴香醚中溶解PPMA(5.52 g,27.0 mmol)、α-GBLMA(6.03 g,35.0 mmol)及TIPEMA(4.31 g,7.8 mmol)來製備進料溶液。藉由在12.63 g茴香醚中溶解2.10 g偶氮引發劑二甲基2,2'-偶氮雙(2-甲基丙酸酯)(由及光純藥工業株式會社(Wako Pure Chemical Industries, Ltd.)以V-601獲得)製備引發劑溶液。聚合反應在裝有水冷凝器及溫度計之三頸圓底燒瓶中進行,以監測燒瓶中之反應。向反應器中加入PPMA(0.47 g,1.42 mmol)、α-GBLMA(0.30 g,2.0 mmol),TIPEMA(0.68 g,1.0 mmol)及17.50 g茴香醚,且將內含物加熱至80℃。使用注射泵將進料溶液及引發劑溶液在4小時內加入反應器中。隨後將內含物再攪拌2小時。將內含物冷卻至室溫,用四氫呋喃(「THF」)稀釋至25重量%,且沈澱成10倍(重量)之甲醇。過濾分離所得共聚物1,且在50℃下真空乾燥24小時。
共聚物 2 由單體PPMA、α-GBLMA、DiHFA、TIPEMA以35/45/10/10之莫耳進料比製備。藉由在17.5 g乙腈及8.8 g四氫呋喃中溶解PPMA(4.41 g,22.0 mmol)、α-GBLMA(4.73 g,28 mmol)、DiHFA(3.09 g,6.0 mmol)及TIPEMA(3.78 g,6.00 mmol)製備單體溶液。聚合反應在裝有水冷凝器及溫度計之三頸圓底燒瓶中進行,以監測燒瓶中之反應。向燒瓶中加入8.5 g單體溶液且加熱至70℃。向剩餘之單體溶液中添加1.53 g引發劑2,2'-偶氮雙(2,4-二甲基戊腈)(由及光純藥工業株式會社以V-65獲得),且使用注射泵將混合物在4小時內加入反應燒瓶中,同時將溫度保持為70℃。然後在相同溫度下再攪拌聚合反應混合物2小時。將內含物冷卻至室溫,且沈澱成10倍(重量)之甲基第三丁基醚。過濾分離所得共聚物2,且在50℃下真空乾燥24小時。
除了使用表2中規定之單體類型及莫耳進料比外,使用用於製備共聚物2之類似程序製備共聚物3。
含有共聚物1及比較聚合物4之光致抗蝕劑組成物各自獨立配製,如表4中所概述。表4中之組分量按總固體計,不包含溶劑。淬滅劑及界面活性劑與光致抗蝕劑1及2中之相同。非聚合物光酸產生劑為DTBPI PFBuS,其具有以下化學結構:
表3及表4中之所有配製物使用丙二醇單甲醚乙酸酯作為溶劑。抗蝕劑在110℃之軟烘烤下加工90秒且在100℃之曝光後基礎下加工60秒。藉由在厚的有機抗反射層上塗覆抗蝕劑產生248奈米之對比曲線。Canon TELACT工具上之抗蝕劑在248奈米下曝光。在曝光後烘烤後,使用0.26 N四甲基氫氧化銨溶液將抗蝕劑顯影60秒。使用KLA Tencore OPTIPROBE™ 7341熱波工具量測膜厚度值。所述評估之結果展示於表5中,其中「248 nm E0
」為以毫焦耳/公分2
為單位表示之248奈米曝光劑量清除。
使用LithoTech Japan EUVES-9000泛光曝光工具獲得EUV曝光源(13.5 nm)之對比曲線量測值。將抗蝕劑旋塗至有機底層或矽晶片上,且在110℃下烘烤90秒以形成40-50 nm厚之光致抗蝕劑膜。抗蝕劑以逐步方式暴露於逐漸增加劑量之13.5 nm輻射,在100℃下曝光後烘烤60秒,且用0.26 N氫氧化四甲基銨水溶液顯影60秒,以形成曝光區及未曝光區之凸紋影像圖案。使用KLA Thermawave-7橢圓計量測每個曝光區之厚度且對劑量繪圖。在10%或更少殘餘之膜厚度下計算劑量清除值(E0
)。所述評估之結果展示於表5中,其中「EUV E」為以毫焦耳/公分2
為單位表示之13.5奈米曝光劑量清除。可看出,與包括無碘三元共聚物之比較光致抗蝕劑2相比,含有含碘TIPEMA重複單元之三元共聚物之光致抗蝕劑1在EUV曝光下具有更高之感光速度。藉由使用不同之光酸產生劑進一步驗證感光速度優勢,因此,與包括無碘聚合物之光致抗蝕劑4相比,含有含碘TIPEMA之三元共聚物之光致抗蝕劑3具有更快的EUV感光速度。 表5
含有本發明共聚物2及3之光致抗蝕劑組成物各自獨立地配製,如表6中所概述。使用LithoTech Japan EUVES-9000泛光曝光工具獲得EUV曝光源(13.5 nm)之對比曲線量測值。將抗蝕劑旋塗至有機底層或矽晶片上,且在110℃下烘烤90秒以形成40-50 nm厚的光致抗蝕劑膜。抗蝕劑以逐步方式暴露於逐漸增加劑量之13.5 nm輻射,在100℃下曝光後烘烤60秒,且用0.26 N氫氧化四甲基銨水溶液顯影60秒,以形成曝光區及未曝光區之凸紋影像圖案。使用KLA Thermawave-7橢圓計量測每個曝光區之厚度且對劑量繪圖。在10%或更少殘餘之膜厚度下計算劑量清除值(E0
)。所述評估之結果展示於表6中,其中「EUV E」為以毫焦耳/公分2
為單位表示之13.5奈米曝光劑量清除。光致抗蝕劑組成物5(其包括含碘四元共聚物)及光致抗蝕劑組成物6(其包括含碘聚合物結合之光酸產生劑)在EUV曝光下展示出優異的敏感度,證明含碘聚合物在光微影圖案化中之廣泛範圍及實用性。 表6
儘管已結合目前視為實用之例示性實施例之內容來描述本發明,但應理解本發明不限於所揭示之實施例,正相反,本發明意欲涵蓋包含在隨附申請專利範圍之精神及範疇內之各種修改及等效安排。
Claims (8)
- 一種共聚物,包括酸可脫保護單體及具有式(I)之單體之聚合產物:
- 如申請專利範圍第1項之共聚物,進一步包括鹼溶性單體、含內酯單體、光酸產生劑或其組合之聚合產物。
- 如申請專利範圍第2項之共聚物,其中所述酸可脫保護單體由式(II)表示,所述鹼溶性單體由式(III)表示,所述含內酯單體由式(IV)表示,且所述光酸產生劑由式(V)表示:
- 一種光致抗蝕劑組成物,包括如申請專利範圍第1項至第3項中任一項之共聚物。
- 如申請專利範圍第5項之光致抗蝕劑組成物,其中G+具有式(VII)、(VIII)或(IX):
- 一種經塗佈之基板,包括:(a)在其表面上具有一或多個待圖案化之層之基板;及(b)在所述一或多個待圖案化之層上方之如申請專利範圍第4項至第6項中任一項之光致抗蝕劑組成物之層。
- 一種形成電子裝置之方法,包括:(a)在所述基板之表面上塗覆如申請專利範圍第4項至第6項中任一項之 光致抗蝕劑組成物之層;(b)將所述光致抗蝕劑組成物層逐圖案地暴露於活化輻射;且(c)使所述暴露之光致抗蝕劑組成物層顯影,以提供抗蝕劑凸紋影像。
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JP6963979B2 (ja) * | 2016-12-14 | 2021-11-10 | 住友化学株式会社 | 樹脂、レジスト組成物及びレジストパターンの製造方法 |
JP7044011B2 (ja) * | 2017-09-13 | 2022-03-30 | 信越化学工業株式会社 | 重合性単量体、重合体、レジスト材料、及びパターン形成方法 |
JP7264020B2 (ja) * | 2018-12-27 | 2023-04-25 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
JP7351256B2 (ja) * | 2019-06-17 | 2023-09-27 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
TWI837443B (zh) * | 2019-12-31 | 2024-04-01 | 南韓商羅門哈斯電子材料韓國公司 | 塗料組成物、經塗覆的基底及形成電子裝置的方法 |
JP7509071B2 (ja) * | 2020-04-28 | 2024-07-02 | 信越化学工業株式会社 | ヨウ素化芳香族カルボン酸型ペンダント基含有ポリマー、レジスト材料及びパターン形成方法 |
US20210341837A1 (en) * | 2020-04-30 | 2021-11-04 | Taiwan Semiconductor Manufacturing Co., Ltd. | Resin, photoresist composition, and method of manufacturing semiconductor device |
JP2021188040A (ja) * | 2020-06-01 | 2021-12-13 | 住友化学株式会社 | 化合物、樹脂、レジスト組成物及びレジストパターンの製造方法 |
JP2021188041A (ja) * | 2020-06-01 | 2021-12-13 | 住友化学株式会社 | 化合物、樹脂、レジスト組成物及びレジストパターンの製造方法 |
JP2022008152A (ja) * | 2020-06-25 | 2022-01-13 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
JP7375697B2 (ja) | 2020-07-17 | 2023-11-08 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
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WO2024142556A1 (ja) * | 2022-12-26 | 2024-07-04 | Jsr株式会社 | 感放射線性樹脂組成物及びパターン形成方法 |
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JP6913055B2 (ja) | 2021-08-04 |
KR20180136887A (ko) | 2018-12-26 |
US20180362752A1 (en) | 2018-12-20 |
US10901316B2 (en) | 2021-01-26 |
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