TWI667286B - 抗蝕劑墊層組成物和使用所述組成物形成圖案的方法 - Google Patents
抗蝕劑墊層組成物和使用所述組成物形成圖案的方法 Download PDFInfo
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- TWI667286B TWI667286B TW107102419A TW107102419A TWI667286B TW I667286 B TWI667286 B TW I667286B TW 107102419 A TW107102419 A TW 107102419A TW 107102419 A TW107102419 A TW 107102419A TW I667286 B TWI667286 B TW I667286B
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Classifications
-
- 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
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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Abstract
本發明揭露一種抗蝕劑墊層組成物,其包含包括由化學
式1和化學式2表示的部分的聚合物和溶劑,且本發明另揭露一種使用所述抗蝕劑墊層組成物形成圖案的方法。
Description
[相關申請的交叉引用]
本發明要求2017年2月3日在韓國智慧財產權局提交的韓國專利申請第10-2017-0015750號的優先權和權益,其全部內容以引用的方式併入本文中。
本發明揭露一種抗蝕劑墊層組成物和一種使用其形成圖案的方法。更具體來說,本發明揭露一種光阻墊層組成物,其用於在半導體基底和光阻層之間形成的墊層,以及涉及一種使用所述墊層形成光阻圖案的方法。
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。這類超精細技術主要需要有效的光刻技術。
典型光刻技術包含在半導體基底上塗布光阻膜並且通過曝光和顯影光阻膜形成光阻圖案。光阻是一種用於轉移基底上的圖像的感光膜。
在形成光阻圖案期間進行曝光是獲得具有高解析度的光阻圖像的重要因素之一。
通過使用啟動的輻射進行光阻的曝光,啟動的輻射通常經反射並且因此限制光阻層中經圖案化的圖像的解析度,並且具體來說,當輻射在基底和光阻層之間的介面上或在夾層硬遮罩上反射時,啟動的輻射散射到光阻區域中,光阻線寬可能變得不均勻並且可能遮擋圖案形式。
另外,光阻墊層組成物應吸收經反射的輻射並且同時具有光阻的高蝕刻選擇性並且在經熱固化之後的後續工藝中需要針對溶劑的耐化學性和到光阻的優良粘附來說明光阻進行圖案化。
為了減少經反射的輻射,已經通過在基底和光阻層之間安置有機層(即所謂的抗蝕劑墊層)來嘗試吸收穿過光阻的光並且同時提高蝕刻選擇性、耐化學性和到光阻的粘附。
本發明的一個實施例提供一種抗蝕劑墊層組成物,其具有平坦化特徵和快速蝕刻速率,並且同時具有預定波長中的吸收特性。
本發明的另一實施例提供一種使用抗蝕劑墊層組成物形成圖案的方法。
根據一個實施例,抗蝕劑墊層組成物包含包括由化學式1和化學式2表示的部分的聚合物和溶劑。
在化學式1中,B是由化學式Z表示的二價基團、氧、經取代或未經取代的C1到C30亞烷基、經取代或未經取代的C1到C30亞雜烷基、經取代或未經取代的C3到C30亞環烷基或其組合,Y和Y'獨立地是單鍵、氧、羰基、-(CH2)O-、-(CH2)S-、-(CH2)NH-或其組合,R2到R9獨立地是氫、羥基、鹵素、經取代或未經取代的乙烯基、經取代或未經取代的C1到C10烷氧基、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C1到C30雜烷基、經取代或未經取代的C2到C30雜芳基或其組合,a、b、c以及d獨立地是0到100範圍內的整數,其限制條件是a和b的總和大於或等於1以及c和d的總和大於或等於1,且*是連接點,[化學式Z]
在化學式Z中,A是經取代或未經取代的芳香族環基團、經取代或未經取代的脂肪族環基團、經取代或未經取代的雜芳香族環基團、經取代或未經取代的雜脂肪族環基團或其組合,X是氫、羥基、經取代或未經取代的C1到C10烷氧基、鹵素、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C6到C30雜芳基、經取代或未經取代的乙烯基或其組合,且*是連接點,
在化學式2中,R1是經取代或未經取代的C1到C30亞烷基、經取代或未經取代的C1到C30亞雜烷基、經取代或未經取代的C3到C30亞環烷基、經取代或未經取代的C6到C30亞芳基、經取代或未經取代的C2到C30亞雜芳基、-((CmH2m)O)n-(m和n中的每一個獨立地是1到10的整數)或其組合,且*是連接點。
在化學式Z中,X可以是經取代或未經取代的C1到C10烷基、經取代或未經取代的C2到C30烯基或經取代或未經取代
的C2到C30炔基。
在化學式Z中,A可以是包含至少一個雜原子的芳香族基團或脂肪族環基團。
在化學式Z中,X可以與A中所包含的雜原子鍵聯。
聚合物的重量平均分子量是1,000到100,000。
抗蝕劑墊層組成物可以更包含具有兩個或更多個交聯位點的交聯劑。
抗蝕劑墊層組成物可以更包含添加劑,所述添加劑為表面活性劑、熱酸產生劑以及塑化劑或其組合。
根據另一實施例,形成圖案的方法包含在基底上形成蝕刻物件層,在蝕刻物件層上塗布抗蝕劑墊層組成物來形成抗蝕劑墊層,在抗蝕劑墊層上形成光阻圖案,並且使用光阻圖案作為蝕刻遮罩依序蝕刻抗蝕劑墊層和蝕刻對象層。
形成光阻圖案可以包含在抗蝕劑墊層上形成光阻層,曝光光阻層並且使光阻層顯影。
在塗布抗蝕劑墊層組成物之後,形成抗蝕劑墊層可以更包含在100℃到500℃的溫度下對抗蝕劑墊層組成物進行熱處理。
因此,可以提供在預定波長中具有吸收特性並且同時具有優良塗料特性的抗蝕劑墊層組成物。
100‧‧‧基底
102‧‧‧薄膜
104‧‧‧抗蝕劑墊層
106‧‧‧光阻層
106a‧‧‧非曝光區域
106b‧‧‧曝光區域
108‧‧‧光阻圖案
110‧‧‧曝光遮罩
112‧‧‧有機層圖案
114‧‧‧薄膜圖案
圖1到圖5是解釋使用根據一個實施例的抗蝕劑墊層組成物形成圖案的方法的橫截面視圖。
本發明的示範性實施例將在下文中進行詳細描述,並且容易被所屬領域的技術人員執行。然而,本發明可以許多不同形式實施,並且不應理解為限於本文所闡述的示範性實施例。
在圖式中,為清楚起見可以放大層、膜、面板、區域等的厚度,並且在整個說明書中相同參考編號表示相同元件。應理解,當如層、膜、區域或基底等元件被稱為在另一元件“上”時,其可以直接在另一元件上或還可以存在***元件。相比之下,當元件被稱為“直接在”另一元件“上”時,不存在***元件。
如本文所用,當未另外提供定義時,術語‘經取代的’可以指化合物的氫原子通過選自以下的取代基置換: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、胺甲醯基、硫醇基、酯基、羧基或其鹽、磺酸基或其鹽、磷酸或其鹽、乙烯基、C1到C20烷基、C2到C20烯基、C2到C20炔基、C6到C30芳基、C7到C30芳基烷基、C6到C30烯丙基、C1到C30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、C3到C30雜環烷基以及其組合。
如本文所用,當未另外提供定義時,術語‘雜’是指包含
1到3個選自N、O、S以及P的雜原子的化合物。
如本文所用,當未另外提供定義時,‘*’指示化合物或化合物部分的連接點。
下文描述根據一個實施例的抗蝕劑墊層組成物。
根據一個實施例的抗蝕劑墊層組成物包含包括由化學式1和化學式2表示的部分的聚合物和溶劑。
在化學式1中,B是由化學式Z表示的二價基團、氧、經取代或未經取代的C1到C30亞烷基、經取代或未經取代的C1到C30亞雜烷基、經取代或未經取代的C3到C30亞環烷基或其組合,Y和Y'獨立地是單鍵、氧、羰基、-(CH2)O-、-(CH2)S-、-(CH2)NH-或其組合,R2到R9獨立地是氫、羥基、鹵素、經取代或未經取代的乙烯基、經取代或未經取代的C1到C10烷氧基、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C1到C30雜烷基、經取代或未經取代的C2到C30雜芳基或其組合,
a、b、c以及d獨立地是0到100範圍內的整數,其限制條件是a和b的總和大於或等於1以及c和d的總和大於或等於1,且*是連接點,
在化學式Z中,A是經取代或未經取代的芳香族環基團、經取代或未經取代的脂肪族環基團、經取代或未經取代的雜芳香族環基團、經取代或未經取代的雜脂肪族環基團或其組合,X是氫、羥基、經取代或未經取代的C1到C10烷氧基、鹵素、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C6到C30雜芳基、經取代或未經取代的乙烯基或其組合,且*是連接點,
其中在化學式2中,R1是經取代或未經取代的C1到C30亞烷基、經取代或未經取代的C1到C30亞雜烷基、經取代或未經取
代的C3到C30亞環烷基、經取代或未經取代的C6到C30亞芳基、經取代或未經取代的C2到C30亞雜芳基、-((CmH2m)O)n-(m和n中的每一個獨立地是1到10的整數)或其組合,且*是連接點。
在化學式1中,B可以是包含由化學式Z表示的環基團的基團、氧、預定線性基團(經取代或未經取代的C1到C30亞烷基、經取代或未經取代的C1到C30亞雜烷基或經取代或未經取代的C3到C30亞環烷基)或其組合。
舉例來說,在化學式1中,B可以是經取代或未經取代的C1到C30亞烷基與氧的組合。舉例來說,在化學式1中,B可以由(但不限於)化學式A表示。
舉例來說,在化學式2中,R1可以由(但不限於)化學式B表示。
在化學式B中,G和G'獨立地是羥基、經取代或未經取代的C1到C10烷氧基、鹵素、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的
C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C6到C30雜芳基、經取代或未經取代的乙烯基或其組合,m和n中的每一個獨立地是1到10範圍內的整數,且*是連接點。
舉例來說,在化學式2中,G和G'可以是(但不限於)羥基。
根據一個實施例,由化學式1表示的部分包含是芳香族環基團或雜芳香族環基團的核(A)和從核的兩側延伸的線性有機基團。
芳香族環基團可以是例如C6到C30並且雜芳香族環基團可以是例如(但不限於)C2到C30。
舉例來說,在化學式1中,由B表示的核可以是例如包含至少一個雜原子的芳香族基團或脂肪族環基團。
舉例來說,在化學式Z中,由A表示的核與由X表示的官能團鍵聯,並且X可以是例如(但不限於)經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基或經取代或未經取代的C2到C30炔基。
舉例來說,在化學式Z中,由X表示的官能團與核(A)的雜原子鍵聯。
舉例來說,可以通過包含兩個或更多個乙烯基的單分子(a)和包含兩個或更多個硫醇基的單分子(b)的化學反應獲得聚合物。
包含兩個或更多個乙烯基的單分子(a)可以包含例如(但不限於)群組1的部分。
抗蝕劑墊層組成物包含具有分別由化學式1和化學式2表示的部分的聚合物,並且因此具有預定折射率(n)和消光係數(k)。因此,當組成物例如用作光阻墊層材料時,經蝕刻的層關於光源可以具有優良吸收,並且因此可以抑制關於光源的光干擾作用。
另外,因為聚合物對有機溶劑和熱穩定,所以當包含化合物的抗蝕劑墊層組成物例如用作光阻墊層材料時,光阻圖案形成
期間由溶劑或熱或產生副產物(如化學材料)等引起的分層以及光阻溶劑引起的頂部厚度損失可以降到最低。另外,化合物具有優良可溶性並且因此可以形成具有優良塗布均勻性的抗蝕劑墊層。
另外,聚合物是高度疏水性的並且因此可以具有到光阻的極佳粘附,並且主鏈中還包含硫(S),並且因此可以實現高折射率並且具有快速蝕刻速率。
另外,聚合物可以是除了上述部分之外包含至少一個來源於另一單分子的第二部分的共聚物。
聚合物的重量平均分子量可以是1,000到100,000。更具體來說,聚合物的重量平均分子量可以是1,000到50,000或1,000到20,000。當聚合物的重量平均分子量在所述範圍內時,包含聚合物的抗蝕劑墊層組成物可以通過調整碳含量和在溶劑中的溶解度來優化。
當聚合物用作抗蝕劑墊層的材料時,不僅可以在烘烤工藝期間在不形成針孔和空隙或使厚度分佈劣化的情況下形成均勻的薄層,而且也可以在下部基底(或層)中具有梯級或形成圖案時獲得優良的間隙填充和平坦化特徵。
溶劑可以是具有足夠可溶性或分散度或聚合物的任一溶劑並且可以包含例如從以下選出的至少一個:丙二醇、丙二醇二乙酸酯、甲氧基丙二醇、二乙二醇、二乙二醇丁基醚、三(乙二醇)單甲基醚、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、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、甲基吡
咯烷酮、甲基吡咯烷酮、乙醯丙酮以及3-乙氧基丙酸乙酯。
按抗蝕劑墊層組成物的總量計,聚合物可以0.1重量%到50重量%、0.1重量%到30重量%或0.1重量%到15重量%的量包含在內。當包含所述範圍內的聚合物時,可以控制抗蝕劑墊層的厚度、表面粗糙度和平坦化。
抗蝕劑墊層組成物可以更包含交聯劑。
交聯劑可以是例如三聚氰胺類、經取代的脲類或聚合物類交聯劑。優選地,其可以是具有至少兩個交聯形成取代基的交聯劑,例如以下化合物,如甲氧基甲基化甘脲、丁氧基甲基化甘脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯並胍胺、丁氧基甲基化苯並胍胺、甲氧基甲基化脲、丁氧基甲基化脲、甲氧基甲基化硫脲或丁氧基甲基化硫脲等。
交聯劑可以是具有高耐熱性的交聯劑,並且可以是例如包含分子中包含芳香族環(例如苯環或萘環)的交聯取代基的化合物。交聯劑可以具有例如兩個或更多個交聯位點。
另外,除了包含由化學式1和化學式2表示的部分的聚合物之外,抗蝕劑墊層組成物可以更包含(但不限於)至少一種其它聚合物:丙烯酸類樹脂、環氧類樹脂、酚醛清漆樹脂、甘脲類樹脂以及三聚氰胺類樹脂。
抗蝕劑墊層組成物可以更包含添加劑,所述添加劑為表面活性劑、熱酸產生劑、塑化劑或其組合。
表面活性劑可以包含例如(但不限於)烷基苯磺酸鹽、烷
基吡啶鎓鹽、聚乙二醇或季銨鹽。
熱酸產生劑可以是例如酸性化合物,如(但不限於)對甲苯磺酸、三氟甲烷磺酸、對甲苯磺酸吡啶鎓、水楊酸、磺基水楊酸、檸檬酸、苯甲酸、羥基苯甲酸、萘碳酸等或/和2,4,4,6-四溴環己二烯酮、安息香甲苯磺酸酯、2-硝基苯甲基甲苯磺酸酯、其它有機磺酸烷基酯等。
按100重量份抗蝕劑墊層組成物計,添加劑可以0.001重量份到40重量份的量存在。在所述範圍內,可以改良溶解度同時不改變抗蝕劑墊層組成物的光學特性。
根據另一實施例,提供使用抗蝕劑墊層組成物製造的抗蝕劑墊層。抗蝕劑墊層可以是在例如基底上塗布抗蝕劑墊層組成物之後,通過熱處理固化的形式。抗蝕劑墊層可以是例如抗反射塗層。
下文中,參看圖1到圖5描述使用抗蝕劑墊層組成物形成圖案的方法。
圖1到圖5是解釋使用根據一個實施例的抗蝕劑墊層組成物形成圖案的方法的橫截面視圖。
參看圖1,製備用於蝕刻的對象。蝕刻物件可以是在半導體基底100上形成的薄膜102。下文中,蝕刻對象限於薄膜102。洗滌薄膜102的整個表面以去除上面殘留的雜質等。薄膜102可以是例如氮化矽層、多晶矽層或氧化矽層。
隨後,將包含包括羥基的丙烯酸酯類樹脂、具有由化學式
1和化學式2表示的部分的聚合物以及溶劑的抗蝕劑墊層組成物旋塗於洗滌過的薄膜102的表面上。
接著,塗布的組成物經乾燥和烘烤,在薄膜102上形成抗蝕劑墊層104。可以在100℃到500℃下進行烘烤,例如在100℃到300℃下進行烘烤。具體來說,抗蝕劑墊層組成物在上文中詳細描述並且因此將省略。
參看圖2,通過在抗蝕劑墊層104上塗布光阻來形成光阻層106。
光阻的實例可以是含有二疊氮萘醌化合物和酚醛清漆樹脂的正型光阻、含有能夠通過曝光解離酸的酸產生劑的化學增幅型正型光阻、在酸存在下分解並且在鹼性水溶液中的可溶性提高的化合物以及堿溶性樹脂、能夠施加提高鹼性水溶液中的可溶性的樹脂的含有堿溶性樹脂的化學增幅型正型光阻等。
隨後,初次烘烤具有光阻層106的基底100。初次烘烤可以在90℃到120℃下進行。
參看圖3,可以選擇性地曝光光阻層106。
光阻層106的曝光可以例如通過在曝光設備的遮罩臺上放置具有預定圖案的曝光遮罩並且在光阻層106上對準曝光遮罩110來進行。隨後,通過向曝光遮罩110中照射光,使基底100上形成的光阻層106的預定區域選擇性地與穿過曝光遮罩的光反應。曝光期間使用的光的實例可以是波長是約193奈米和約248奈米的ArF鐳射(ArF的鐳射),波長是約13.5奈米的FUV(遠紫外
光)等。
光阻層106的曝光區域106b與光阻層106的非曝光區域106a相比是相對親水性的。因此,光阻層106的曝光區域106b和非曝光區域106a可以具有彼此不同的溶解度。
隨後,二次烘烤基底100。二次烘烤可以在90℃到150℃下進行。光阻層的曝光區域106b由於二次烘烤變得容易被預定溶劑溶解。
參看圖4,光阻層的曝光區域106b被顯影溶液溶解和去除,形成光阻圖案108。具體來說,通過使用顯影溶液(如四甲基氫氧化銨(TMAH)等)溶解和去除光阻層的曝光區域106b,精製光阻圖案108。
隨後,使用光阻圖案108作為蝕刻遮罩來蝕刻抗蝕劑墊層。通過上述蝕刻,形成有機層圖案112。
蝕刻可以是例如使用蝕刻氣體的幹式蝕刻,並且蝕刻氣體可以是例如CHF3、CF4、Cl2、BCl3以及其混合氣體。
參看圖5,施加光阻圖案108作為蝕刻遮罩來蝕刻經曝光的薄膜102。因此,薄膜形成薄膜圖案114。
下文中,經關於聚合物合成和包含其的抗蝕劑墊層組成物的製備的實例更詳細描述本發明。然而,本發明技術上不受以下示範性實施例限制。
合成實例
合成實例1
將30克異氰尿酸1,3-二烯丙基-5-(2-羥乙基)酯、11.16克1,2-乙烷二硫醇、0.389克AIBN以及166克二甲基甲醯胺置於500毫升2頸圓形燒瓶中,並且將冷凝器連接到燒瓶。溫度升高到80℃並且反應進行2.5小時之後,將獲得的反應溶液冷卻到室溫。隨後,將反應溶液移到1升廣口瓶,用己烷洗滌三次,接著用***和純水依序洗滌。將獲得的膠狀物狀態的樹脂完全溶解於80克THF中,並且將溶液緩慢添加到正在攪拌的700克甲苯中。將其中的溶劑排出之後,通過使用真空泵去除其中仍剩餘的溶劑,獲得包含由化學式1-1表示的結構單元的聚合物(Mw=5,100)。
合成實例2
將14.96克氰尿酸三烯丙酯、3.81克EDT(乙烷二硫醇)、0.2克AIBN以及25克二甲基甲醯胺置於500毫升2頸圓形燒瓶中,並且將冷凝器連接到燒瓶。溫度升高到80℃並且反應進行2.5小時之後,將獲得的反應溶液冷卻到室溫。隨後,將反應溶液移到1升廣口瓶並且用純水和甲苯依序洗滌。將膠狀物狀態的樹脂完全溶解於80克THF中,並且將溶液以逐滴方式緩慢添加到正在攪
拌的700克己烷中。將溶劑排出之後,通過使用真空泵去除其中仍剩餘的溶劑,獲得包含由化學式1-2表示的結構單元的聚合物(Mw=17,000)。
(其中,在化學式中,m=70摩爾%且n=30摩爾%)
合成實例3
根據與合成實例2相同的方法獲得包含由化學式1-3表示的結構單元的聚合物(Mw=2,700),但向500毫升2頸圓形燒瓶中放入32.1克二烯丙基醚、20.7克二硫蘇糖醇、0.5克AIBN以及210克DMF。
合成實例4
根據與合成實例2相同的方法獲得包含由化學式1-4表示的結構單元的聚合物(Mw=8,400),但向500毫升2頸圓形燒瓶
中放入32.1克1,6-己二醇二丙烯酸酯、20.7克二硫蘇糖醇、0.5克AIBN以及210克DMF。
合成實例5
根據與合成實例2相同的方法獲得包含由化學式1-5表示的結構單元的聚合物(Mw=2,900),但向500毫升2頸圓形燒瓶中放入30.4克三乙二醇二乙烯醚、20.7克二硫蘇糖醇、0.5克AIBN以及206克DMF。
合成實例6
根據與合成實例2相同的方法獲得包含由化學式1-6表示的結構單元的聚合物(Mw=3,200),但向500毫升2頸圓形燒瓶中放入29.4克1,4-環己烷二甲醇二乙烯醚、20.7克二硫蘇糖醇、0.5克AIBN以及206克DMF。
[化學式1-6]
合成實例7
根據與合成實例2相同的方法獲得包含由化學式1-7表示的結構單元的聚合物(Mw=4,500),但向500毫升2頸圓形燒瓶中放入23.7克二(乙二醇)二乙烯醚、20.7克二硫蘇糖醇、0.5克AIBN以及206克DMF。
合成實例8
根據與合成實例2相同的方法獲得包含由化學式1-8表示的結構單元的聚合物(Mw=4,200),但向500毫升2頸圓形燒瓶中放入23.7克對苯二甲酸二烯丙酯、20.4克二硫蘇糖醇、0.5克AIBN以及206克DMF。
合成比較例1
將40克甲基丙烯酸甲酯、52.1克2-羥基丙烯酸酯、70.4
克丙烯酸苯甲酯、2克AIBN以及306克二噁烷置於500毫升2頸圓形燒瓶中,並且將冷凝器連接到燒瓶。溫度升高到80℃並且反應進行2.5小時之後,將獲得的反應溶液冷卻到室溫。將反應溶液移到3L廣口瓶並且用己烷洗滌。獲得的樹脂在30℃真空烘箱中乾燥以去除剩餘的溶劑,並且獲得包含由化學式2表示的結構單元的聚合物(Mw=12,000)。
製備抗蝕劑墊層組成物
實例1到實例8以及比較例1
將合成實例1的聚合物和PD1174(硬化劑,TCI,按100重量份聚合物計的15重量份)和對甲苯磺酸吡啶鎓(按100重量份聚合物計的1重量份)溶解於丙二醇單甲基醚和乳酸乙酯的混合溶劑(混合重量比=1:1)中,並且攪拌溶液6小時來製備抗蝕劑墊層組成物。
測定混合溶劑的量,其中按抗蝕劑墊層組成物的總重量計,包含1重量%固體含量的聚合物。
實例2到實例8
抗蝕劑墊層組成物中的每一個根據與實例1相同的方法
製備,但使用根據合成實例2到合成實例8的各聚合物。
比較例1
根據與實例1相同的方法製備抗蝕劑墊層組成物,但使用根據合成比較例1的聚合物。
評估光學特性
分別取用2毫升根據實例1到實例8和比較例1的組成物,施加在4英寸晶片上,並且使用旋塗器(三笠株式會社(Mikasa Co.,Ltd.))在1,500rpm下旋塗20秒。隨後,在210℃下固化塗布的組成物持續90秒,形成各30奈米厚的薄膜。在300 A的條件下,通過使用VASE橢偏儀(J.A.伍拉姆公司(J.A.Woollam Co.))測量各薄膜的折射率(n)和消光係數(k)。結果示於表1中。
參看表1,使用分別包含由化學式1表示的結構單元的聚合物的組成物(實例1到實例8)製造的抗蝕劑底層顯示優良折射率(n)和消光係數(k),並且因此在使用短波長的光形成光阻圖案期間有效吸收反射的光並且提供具有令人滿意的形狀的圖案。
雖然已經結合目前視為實用示範性實施例的內容來描述本發明,但應理解本發明不限於所披露的實施例,而是相反,本發明旨在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等效配置。
Claims (10)
- 一種抗蝕劑墊層組成物,包括:包含由化學式1和化學式2表示的部分的聚合物;以及溶劑,其中,在化學式1中,B是由化學式Z表示的二價基團、氧、經取代或未經取代的C1到C30亞烷基、經取代或未經取代的C1到C30亞雜烷基、經取代或未經取代的C3到C30亞環烷基或其組合,Y和Y'獨立地是單鍵、氧、羰基、-(CH2)O-、-(CH2)S-、-(CH2)NH-或其組合,R2、R3、R8以及R9獨立地是氫、鹵素、經取代或未經取代的乙烯基、經取代或未經取代的C1到C10烷氧基、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C1到C30雜烷基、經取代或未經取代的C2到C30雜芳基或其組合,R4到R7獨立地是氫、羥基、鹵素、經取代或未經取代的乙烯基、經取代或未經取代的C1到C10烷氧基、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C1到C30雜烷基、經取代或未經取代的C2到C30雜芳基或其組合,a、b、c以及d獨立地是0到100範圍內的整數,其限制條件是a和b的總和大於或等於1以及c和d的總和大於或等於1,且*是連接點,其中在化學式Z中,A是經取代或未經取代的芳香族環基團、經取代或未經取代的脂肪族環基團、經取代或未經取代的雜芳香族環基團、經取代或未經取代的雜脂肪族環基團或其組合,X是氫、羥基、經取代或未經取代的C1到C10烷氧基、鹵素、經取代或未經取代的C1到C30烷基、經取代或未經取代的C2到C30烯基、經取代或未經取代的C2到C30炔基、經取代或未經取代的C6到C30芳基、經取代或未經取代的C6到C30雜芳基、經取代或未經取代的乙烯基或其組合,且*是連接點:[化學式2]其中在化學式2中,R1是經取代或未經取代的C1到C30亞烷基、經取代或未經取代的C1到C30亞雜烷基、經取代或未經取代的C3到C30亞環烷基、經取代或未經取代的C6到C30亞芳基、經取代或未經取代的C2到C30亞雜芳基、-((CmH2m)O)n-或其組合,其中m和n中的每一個獨立地是1到10的整數,且*是連接點,上述的術語“經取代的”意指化合物基團的氫原子經選自以下的取代基置換:羥基、羰基、硫醇基、乙烯基、C1到C20烷基、C2到C20烯基、C1到C30烷氧基、C1到C20雜烷基以及其組合。
- 如申請專利範圍第1項所述的抗蝕劑墊層組成物,其中在化學式Z中,X是經取代或未經取代的C1到C10烷基、經取代或未經取代的C2到C30烯基或經取代或未經取代的C2到C30炔基。
- 如申請專利範圍第1項所述的抗蝕劑墊層組成物,其中在化學式Z中,A是包含至少一個雜原子的芳香族基團或脂肪族環基團。
- 如申請專利範圍第3項所述的抗蝕劑墊層組成物,其中在化學式Z中,X與A中所包含的雜原子鍵結。
- 如申請專利範圍第1項所述的抗蝕劑墊層組成物,其中所述聚合物的重量平均分子量是1,000到100,000。
- 如申請專利範圍第1項所述的抗蝕劑墊層組成物,其中所述抗蝕劑墊層組成物更包含具有兩個或更多個交聯位點的交聯劑。
- 如申請專利範圍第1項所述的抗蝕劑墊層組成物,其中所述抗蝕劑墊層組成物更包含添加劑,所述添加劑為表面活性劑、熱酸產生劑和塑化劑或其組合。
- 一種形成圖案的方法,包括:在基底上形成蝕刻物件層;在所述蝕刻物件層上塗布如申請專利範圍第1項所述的抗蝕劑墊層組成物以形成抗蝕劑墊層;在所述抗蝕劑墊層上形成光阻圖案;以及使用所述光阻圖案作為蝕刻遮罩以依序蝕刻所述抗蝕劑墊層和所述蝕刻對象層。
- 如申請專利範圍第8項所述的形成圖案的方法,其中形成所述光阻圖案包含:在所述抗蝕劑墊層上形成光阻層;曝光所述光阻層;以及顯影所述光阻層。
- 如申請專利範圍第8項所述的形成圖案的方法,其中在塗布所述抗蝕劑墊層組成物之後,形成所述抗蝕劑墊層更包含在100℃到500℃的溫度下對所述抗蝕劑墊層組成物進行熱處理。
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