TWI553038B - 聚合物、有機層組成物、有機層以及形成圖案的方法 - Google Patents
聚合物、有機層組成物、有機層以及形成圖案的方法 Download PDFInfo
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- TWI553038B TWI553038B TW104124533A TW104124533A TWI553038B TW I553038 B TWI553038 B TW I553038B TW 104124533 A TW104124533 A TW 104124533A TW 104124533 A TW104124533 A TW 104124533A TW I553038 B TWI553038 B TW I553038B
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- 230000003746 surface roughness Effects 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 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
Classifications
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Description
本申請案主張2014年9月30日在韓國智慧財產局提申的韓國專利申請案第10-2014-0131589號的優先權和權益,所述申請案的全部內容以引用的方式併入本文中。
揭露一種聚合物、一種包含所述聚合物的有機層組成物、一種由所述有機層組成物製成的有機層以及一種使用所述有機層組成物形成圖案的方法。
最近,半導體行業已經研發出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微影技術。典型的微影技術包含:在半導體基底上提供材料層;在所述材料層上塗布光阻層;使所述光阻層曝光並且顯影以提供光阻圖案;以及使用所述光阻圖案作為罩幕來蝕刻所述材料層。現如今,
根據待形成的圖案的小型化,僅僅藉由上述典型微影技術難以提供具有極佳輪廓的精細圖案。因此,可以在材料層與光阻層之間形成被稱為硬罩幕層的有機層來提供精細圖案。硬罩幕層起到中間層的作用,用於藉由選擇性蝕刻製程來將光阻的精細圖案轉移到材料層。因此,需要硬罩幕層具有如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,最近已經提出了藉由旋塗法代替化學氣相沈積來形成硬罩幕層。旋塗法易於進行並且還可以改良間隙填充特徵和平面化特徵。需要用薄膜填充圖案的間隙填充特徵,因為多個圖案對於獲得精細圖案而言是必需的。此外,當作為塗層基底的晶圓具有凸塊或具有較稠密圖案區和無圖案區時,需要使薄膜表面平面化的平面化特徵。需要研發滿足硬罩幕層特徵的有機層材料。
本發明是關於一種聚合物、包含所述聚合物的有機層組成物、藉由固化所述有機層組成物形成的有機層以及使用有機層組成物形成圖案的方法。所述聚合物同時確保抗蝕刻性和平面化特徵。
根據一個實施例,提供包含由以下化學式1表示的部分的聚合物。
在化學式1中,A1和A2獨立地是衍生自以下族群1所列化合物中的一者的二價基團,A3是以下族群2所列基團中的一者,以及m是0或1。
在族群1中,R1、R2和R3獨立地是氫(-H)、羥基(-OH)、氧(O)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基或其組合,Z1到Z6獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷胺基(alkylamine group)、經取代或未經取代的C7到C20芳烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,以及a、b、c、d、e以及f獨立地是0到2的整數。
在族群2中,X1和X2獨立地是經取代或未經取代的C6到C50伸芳基、經取代或未經取代的C1到C10含環氧烷的基團或其組合,Y1和Y2獨立地是經取代或未經取代的C6到C30芳基,
Z7到Z10獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷胺基、經取代或未經取代的C7到C20芳烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,以及g、h、i以及j獨立地是0到2的整數。
根據一個實施例,在族群2中,X1和X2可以獨立地是衍生自以下族群3所列化合物中的一者的二價基團。
根據一個實施例,在族群2中,Y1和Y2可以獨立地是衍生自以下族群3所列化合物中的一者的單價基團。
根據一個實施例,在族群2中,X2、Y1和Y2中的至少一者可以是衍生自經取代或未經取代的苯、經取代或未經取代的
萘、經取代或未經取代的聯苯、經取代或未經取代的芘(pyrene)、經取代或未經取代的苝(perylene)、經取代或未經取代的苯並苝(benzoperylene)、經取代或未經取代的蔻(coronene)或其組合的基團。
根據一個實施例,在族群1中,R1、R2和R3可以獨立地是氫(-H)或經取代或未經取代的苯基。
根據一個實施例,聚合物可以由以下化學式2-1到化學式2-10中的一者表示。
在化學式2-1到化學式2-10中,R4和R5獨立地是氫(-H)、氧(O)、甲氧基(-OCH3)、乙氧基(-OC2H5)、羥基(-OH)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基或其組合,Z11到Z22獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經
取代的C1到C20烷胺基、經取代或未經取代的C7到C20芳烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,k、l、m、n、o、p、q、r、s、t、u以及v獨立地是0到2的整數,以及n0、n1以及n2是2到300的整數。
根據一個實施例,聚合物的重量平均分子量可以是約1,000到約200,000。
根據另一實施例,提供一種包含聚合物和溶劑的有機層組成物。
根據一個實施例,以有機層組成物的總量計,聚合物可以以約0.1重量%到約30重量%的量被包含在內。
根據又一實施例,提供藉由固化有機層組成物形成的有機層。
根據另一實施例,一種形成圖案的方法包含:在基底上提供材料層,在所述材料層上塗覆有機層組成物,熱處理所述有機層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,使所述光阻層曝光並且顯影以形成光阻圖案,使用所述光阻圖案選擇性地移除所述含矽薄層和所述硬罩幕層以使一部分所述材料層暴露,以及蝕刻所述材料層的
暴露部分。
根據一個實施例,有機層組成物可以使用旋塗法塗覆。
根據一個實施例,形成有機層的製程可以包含約100℃到約500℃下的熱處理。
根據一個實施例,所述方法可以進一步包含在形成光阻層之前形成底部抗反射塗層(bottom antireflective coating,BARC)。
可以提供同時確保抗蝕刻性和平面化特徵的有機層。
圖1繪示用於評估平面化特徵的計算方程式2。
下文將詳細地描述本發明的例示性實施例,並且於相關領域中具通常知識者可以容易地執行所述例示性實施例。然而,本發明可以用多種不同形式實施,並且不應解釋為受限於本文所闡述的例示性實施例。
如本文所用,當未另外提供定義時,術語‘經取代的’可以指被由以下各項中選出的取代基取代而代替化合物的氫原子的一類:鹵素原子(F、Br、Cl或I)、羥基、烷氧基、硝基、氰基、氨基、疊氮基、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、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個由B、N、O、S和P中選出的雜原子的一類。
如本文所用,當未另外提供定義時,‘*’表示化合物或化合物部分的鍵聯點。
此外,衍生自A化合物的‘單價基團’是指在A化合物中取代一個氫的單價基團。舉例來說,衍生自苯族群的單價基團變成苯基。此外,衍生自A化合物的‘二價基團’是指在A化合物中取代兩個氫以形成兩個鍵聯點的二價基團。舉例來說,衍生自苯族群的二價基團變成伸苯基。
下文描述根據一個實施例的聚合物。
根據一個實施例的聚合物包含由以下化學式1表示的部分。
在化學式1中,A1和A2獨立地是衍生自以下族群1所列化合物中的一者的二
價基團,A3是以下族群2所列基團中的一者,以及m是0或1。
在族群1中,R1、R2和R3獨立地是氫(-H)、羥基(-OH)、氧(O)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取
代或未經取代的C6到C30芳基或其組合,Z1到Z6獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷胺基、經取代或未經取代的C7到C20芳烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,以及a、b、c、d、e以及f獨立地是0到2的整數。
在族群2中,X1和X2獨立地是經取代或未經取代的C6到C50伸芳基、經取代或未經取代的C1到C10含環氧烷的基團或其組合,Y1和Y2獨立地是經取代或未經取代的C6到C30芳基,Z7到Z10獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經
取代的C1到C20烷胺基、經取代或未經取代的C7到C20芳烷基、經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,以及g、h、i以及j獨立地是0到2的整數。
聚合物具有使苯甲基氫(benzylic hydrogen)達到最少而環參數達到最大的結構,並且可以確保極佳的抗蝕刻性。
此外,聚合物在其單體結構中包含叔碳(tertiary carbon)與季碳(quaternary carbon)中的至少任一者。在本說明書中,叔碳表示與將鍵結於所述碳的全部四個氫中的三個氫取代的三個其他基團鍵結的碳,而季碳表示與將全部四個氫取代的四個其他基團鍵結的碳。
當包含這些碳原子的聚合物被包含在有機層組成物內時,硬罩幕層的溶解經改良,並且因此,可以容易地應用旋塗法。包含叔碳或季碳的化合物的部分與族群2中所示的相同。
聚合物可以包含至少一個由化學式1表示的部分,並且多個部分可以具有相同結構或彼此不同的結構。
舉例來說,在族群2中,X1和X2可以是衍生自以下族群3所列化合物中的一者的二價基團。
族群3中提供的芳香族環基可以是經取代或未經取代的基團。
舉例來說,族群2中X1與X2中的至少任一者的結構可以包含類似以下鍵聯基團A的環氧烷基。
在鍵聯基團A中,n和m獨立地是1到10範圍內的整數。
舉例來說,在族群2中,Y1和Y2可以獨立地是衍生自以下族群3所列化合物中的一者的單價基團。
另一方面,聚合物可以在由化學式1表示的部分中包含至少一個多環芳香族環基。因此,可以確保聚合物的光學特性並且同時可以進一步改良抗蝕刻性。
舉例來說,在族群2中,X2、Y1和Y2中的至少一者可以是例如衍生自經取代或未經取代的苯、經取代或未經取代的萘、
經取代或未經取代的聯苯、經取代或未經取代的芘、經取代或未經取代的苝、經取代或未經取代的苯並苝、經取代或未經取代的蔻或其組合的基團,但是不限於此。
聚合物的特性可以藉由選擇Z1到Z10的類別和數量來容易地調節,所述Z1到Z10表示在環基中經取代的官能基。
舉例來說,表示在化學式1中鍵結到氮(N)原子的官能基的R1、R2和R3獨立地是氫(-H)或經取代或未經取代的苯基,但是不限於此。
聚合物可以例如由以下化學式2-1到化學式2-10中的一者表示。
在化學式2-1到化學式2-10中,R4和R5獨立地是氫(-H)、羥基(-OH)、氧、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基或其組合,Z11到Z22獨立地是羥基(-OH)、甲氧基(-OCH3)、乙氧基(-OC2H5)、鹵素(-F、-Cl、-Br、-I)、經取代或未經取代的C6到C30芳基、經取代或未經取代的C3到C30環烯基、經取代或未經取代的C1到C20烷胺基、經取代或未經取代的C7到C20芳烷基、
經取代或未經取代的C1到C20雜烷基、經取代或未經取代的C2到C30雜環烷基、經取代或未經取代的C2到C30雜芳基、經取代或未經取代的C1到C4烷基醚基、經取代或未經取代的C7到C20芳基伸烷基醚基、經取代或未經取代的C1到C30鹵烷基或其組合,k、l、m、n、o、p、q、r、s、t、u以及v獨立地是0到2的整數,以及n0、n1以及n2是2到300的整數。
聚合物的重量平均分子量可以是約1,000到約200,000。當聚合物的重量平均分子量在所述範圍內時,可以調節並且因此優化包含聚合物的有機層組成物(例如硬罩幕組成物)的碳量和溶解度。
根據另一實施例,提供一種包含聚合物和溶劑的有機層組成物。
溶劑可以是足以溶解或分散聚合物的任一者,並且可以是例如由以下各項中選出的至少一者:丙二醇、丙二醇二乙酸酯、甲氧基丙二醇、二甘醇、二甘醇丁基醚、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、甲基吡咯烷酮以及乙醯丙酮。
以有機層組成物的總量計,聚合物可以以約0.1重量%到約30重量%的量被包含在內。當聚合物在所述範圍內被包含時,可以控制有機層的厚度、表面粗糙度和平面化。
有機層組成物可以進一步包含表面活性劑、交聯劑、熱酸產生劑、塑化劑等添加劑。
表面活性劑可以包含例如烷基苯磺酸鹽、烷基吡啶鎓鹽、聚乙二醇或季銨鹽,但是不限於此。
交聯劑可以是例如其三聚氰胺類、經取代的脲類或聚合物類的試劑。較佳地,具有至少兩種交聯形成性取代基的交聯劑可以是例如以下化合物,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、甲氧基甲基化苯胍胺、丁氧基甲基化苯胍胺、甲氧基甲基化脲、丁氧基甲基化脲、甲氧基甲基化硫脲等。
熱酸產生劑可以是例如酸性化合物,如對甲苯磺酸、三氟甲磺酸、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、甲苯磺酸安息香酯、甲苯磺酸2-硝基苯甲酯、其他有機磺酸烷基酯等,但是不限於此。
以有機層組成物的100重量份計,添加劑可以以約0.001重量份到40重量份的量被包含在內。當添加劑在所述範圍內被包含時,可以在不改變有機層組成物的光學特性的情況下提高溶解度。
根據另一實施例,提供一種使用有機層組成物製造的有機層。有機層可以例如藉由在基底上塗布有機層組成物並且對其熱進行處理以固化來形成,並且可以包含例如硬罩幕層、平面化
層、犧牲層、填充物等以用於電子裝置。
下文描述一種藉由使用有機層組成物來形成圖案的方法。
根據另一實施例的形成圖案的方法包含:在基底上提供材料層,在所述材料層上塗覆包含聚合物和溶劑的有機層組成物,熱處理所述有機層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,使所述光阻層曝光並且顯影以形成光阻圖案,使用所述光阻圖案選擇性地移除所述含矽薄層和所述硬罩幕層以使一部分所述材料層暴露,以及蝕刻所述材料層的暴露部分。
基底可以是例如矽晶圓、玻璃基底或聚合物基底。
材料層是待最終圖案化的材料,例如金屬層,如鋁層和銅層;半導體層,如矽層;或絕緣層,如氧化矽層和氮化矽層。材料層可以藉由如化學氣相沈積(chemical vapor deposition,CVD)製程的方法形成。
有機層組成物與上文所述的相同,並且可以以溶液形式藉由旋塗法來塗覆。本文中,有機層組成物的厚度是不受特定限制的,但可以是例如約50埃到約10,000埃。
可以在例如約100℃到約500℃下對有機層組成物進行熱處理持續約10秒到1小時。
含矽薄層可以由例如以下材料形成:如SiCN、SiOC、SiON、SiOCN、SiC和/或SiN等。
所述方法可進一步包含在形成光阻層之前形成底部抗反射塗層(BARC)。
光阻層的曝光可以使用例如ArF、KrF或EUV進行。曝光之後,可以在約100℃到約500℃下進行熱處理。
可以使用蝕刻氣體藉由乾式蝕刻製程進行材料層的暴露部分的蝕刻製程,並且蝕刻氣體可以是例如(但不限於)CHF3、CF4、Cl2、BCl3以及其混合氣體。
可以以多個圖案形成經蝕刻的材料層,並且這多個圖案可以是金屬圖案、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。
下文參考實例更詳細地說明本發明。然而,這些實例是例示性的,並且本發明不限於此。
合成實例
合成比較例1
將21.6克(0.057莫耳)9,9-雙(4-甲氧苯基)-9H-茀和9.6克(0.057莫耳)1,4-雙(甲氧基甲基)苯連續放入配備有溫度計、冷凝器和機械攪拌器的500毫升燒瓶中,並且隨後溶解於51克丙二醇單甲基醚乙酸酯(propylene glycol monomethyl ether acetate,PGMEA)中。隨後,向其中添加0.15克(0.001莫耳)亞硫酸二乙酯,並且在90℃到120℃下攪拌混合物5小時到10小時。當每一小時從聚合反應的反應物採集的樣本的重量平均分子量是1,800到2,300時,終止反應。
當聚合反應終止時,接著將反應物冷卻到室溫,並且隨後添加到40克蒸餾水和400克甲醇中並劇烈攪拌混合物,並且使其靜置。隨後,將在從其中移除上清液之後獲得的沉澱溶解於80克丙二醇單甲基醚乙酸酯(PGMEA)中,藉由使用40克甲醇和40克水劇烈攪拌溶液,並且隨後使其靜置(第一製程)。隨後,將在從其中移除上清液之後獲得的沉澱再次溶解於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純化製程,並且此純化製程總計進行三次。將經純化的聚合物溶解於80克丙二醇單甲基醚乙酸酯(PGMEA)中,在減壓下移除溶液中剩餘的甲醇和蒸餾水,獲得由以下化學式A表示的聚合物(重量平均分子量(weight average molecular weight,Mw)=2500)。
合成比較例2
根據與合成比較例1相同的方法,藉由使用23.2克(0.1莫耳)4-甲氧基芘、33.2克(0.2莫耳)1,4-雙(甲氧基甲基)苯、15.8克(0.1莫耳)1-甲氧基萘、72.2克丙二醇單甲基醚乙酸酯(PGMEA)以及0.62克(4毫莫耳)硫酸二乙酯,獲得由以下化學式B表示的聚合物(重量平均分子量(Mw)=2500)。
合成比較例3
將30.0克(0.1莫耳)蔻和34克(0.2莫耳)2-萘甲醯氯放入配備有機械攪拌器和冷卻套管的500毫升二頸燒瓶中並且溶解於300克1,2-二氯乙烷中。十五分鐘後,向其中緩慢添加15克(0.11莫耳)三氯鋁,並且隨後在室溫下使反應溶液反應5小時。當反應終止時,用水處理所得物以移除三氯鋁,並且用蒸發器濃縮殘餘物。緊接著,將160克四氫呋喃添加到所得化合物中,獲得溶液。隨後,將16克(0.42莫耳)硼氫化鈉水溶液緩慢添加到溶液中,並且在室溫下攪拌混合物12小時。當反應終止時,用7%氯化氫溶液將所得物酸化到最多pH 5,並用乙酸乙酯萃取,並且使有機溶劑減壓,獲得由以下化學式C表示的化合物。
合成比較例4
將40.4克(0.2莫耳)芘和20克(0.1莫耳)對酞醯氯放入配備有機械攪拌器和冷卻套管的500毫升二頸燒瓶中並且溶解於300克1,2-二氯乙烷中。15分鐘之後,向其中緩慢添加15克(0.11莫耳)三氯鋁,並且在室溫下使所得反應溶液反應5小時。當反
應終止時,使用水從其中移除三氯鋁,並且用蒸發器濃縮殘餘物。隨後,將160克四氫呋喃添加到所得化合物中,獲得溶液。緊接著,將16克(0.42莫耳)硼氫化鈉水溶液緩慢添加到溶液中,並且在室溫下攪拌混合物12小時。當反應終止時,用7%氯化氫溶液將所得物酸化到最多pH 5,並用乙酸乙酯萃取,並且使其中的有機溶劑減壓,獲得由以下化學式D表示的化合物。
合成比較例5
除了使用苝代替蔻以及苯甲醯氯代替2-萘甲醯氯以外,根據與合成比較例3相同的方法獲得由以下化學式E表示的化合物。
合成實例1
將11.7克(0.1莫耳)1H-吲哚、18克(0.1莫耳)9-芴酮、9.5克(0.05莫耳)對甲苯磺酸水合物以及91克1,4-二氧雜環放入燒瓶中並且在100℃下攪拌。當每一小時結束時從聚合反應的反應物採集的樣本的重量平均分子量達到2000到3000時,終止反應。當反應終止時,向其中添加100克己烷以萃取1,4-二氧雜環,
過濾藉由向其中添加甲醇而獲得的沉澱,並且藉由使用甲醇移除其中剩餘的單體,獲得由以下化學式1aa表示的聚合物(重量平均分子量(Mw)=2500)。
合成實例2
除了使用19.3克(0.1莫耳)2-苯基-1H-吲哚、18克(0.1莫耳)9-芴酮、9.5克(0.05莫耳)對甲苯磺酸水合物以及91克1,4-二氧雜環以外,根據與合成實例1相同的方法獲得由以下化學式1bb表示的聚合物(重量平均分子量(Mw)=2300)。
合成實例3
將1克(3.2毫莫耳)4,4'-二溴聯苯溶解於20毫升四氫呋喃中,並且在-78℃下向其中以逐滴方式緩慢添加3毫升2.5M n-BuLi(於己烷中)。30分鐘之後,向其中以逐滴方式緩慢添加溶解於THF中的1.2克(6.4毫莫耳)9-芴酮,並且在室溫下攪拌混合物15小時。藉由使用1N鹽酸將所得反應溶液設定成pH=7並用EtOAc萃取,並且移除其中的溶劑。藉由柱色譜法分離其中的產品,獲得化合物S1(合成化學式S1)。
接著,根據與合成實例1相同的方法,藉由使用5.9克(50毫莫耳)1H-吲哚、25.7克(50毫莫耳)化合物S1、4.7克(25毫莫耳)對甲苯磺酸水合物以及85克1,4-二氧雜環,獲得由化學式1cc表示的聚合物(重量平均分子量(Mw)=2900)。
合成實例4
根據與合成實例1相同的方法,藉由使用8.0克(30毫莫耳)9H-二苯並[a,c]哢唑、15.4克(30毫莫耳)化合物S1、5.7克(30毫莫耳)對甲苯磺酸水合物以及117克1,4-二氧雜環,獲得由化學式1dd表示的聚合物(重量平均分子量(Mw)=2800)。
合成實例5
將6.08克(0.01莫耳)由化學式C表示的化合物、1.93克(0.01莫耳)N-苯基吲哚、1.9克(0.01莫耳)對甲苯磺酸水合物以及
25克1,4-二氧雜環放入燒瓶中並且在100℃下攪拌。當每一小時從聚合反應的反應物採集的樣本的重量平均分子量是2500到3500時,終止反應。當反應終止時,向其中添加100克己烷以萃取1,4-二氧雜環,向其中添加水和甲醇,過濾其中的沉澱,並且藉由使用甲醇移除其中剩餘的單體,獲得由以下化學式1ee表示的聚合物(重量平均分子量(MW)=3300)。
合成實例6
除了使用由化學式D表示的化合物代替由化學式C表示的化合物以及5,7-二氫-吲哚[2,3-b]哢唑代替N-苯基吲哚以外,根據合成實例5獲得由以下化學式1ff表示的聚合物(重量平均分子量(MW)=3100)。
合成實例7
除了使用由化學式E表示的化合物代替由化學式C表示的化
合物以及2,3'-二吲哚代替N-苯基吲哚以外,根據與合成實例5相同的方法獲得由以下化學式1gg表示的聚合物(重量平均分子量(MW)=3200)。
合成實例8
除了使用16.7克(0.1莫耳)哢唑、18克(0.1莫耳)9-芴酮、19克(0.1莫耳)對甲苯磺酸單水合物以及46克1,4-二氧雜環以外,根據與合成實例1相同的方法獲得由以下化學式1hh表示的聚合物(重量平均分子量(Mw)=2300)。
合成實例9
除了使用16.7克(0.1莫耳)哢唑、53克(0.1莫耳)由化學式D表示的化合物、19克(0.1莫耳)對甲苯磺酸單水合物以及55克1,4-二氧雜環以外,根據與合成實例5相同的方法獲得由以下化學式1ii表示的聚合物(重量平均分子量(Mw)=2100)。
合成實例10
除了使用8.3克(0.05莫耳)哢唑、9.7克(0.05莫耳)2-苯基-1H-吲哚、18克(0.1莫耳)9-芴酮、19克(0.1莫耳)對甲苯磺酸單水合物以及46克1,4-二氧雜環以外,根據與合成實例5相同的方法獲得由以下化學式1jj表示的聚合物(重量平均分子量(Mw)=2300)。
製備硬罩幕組成物
實例1
將合成實例1的化合物溶解於丙二醇單甲基醚乙酸酯(PGMEA)與環己酮(7:3(體積/體積))的混合溶劑中,並且過濾溶液,製備硬罩幕組成物。以取決於所要厚度的硬罩幕組成物總重量計,將化合物的量調節在3重量%到15重量%的範圍內。
實例2
除了使用合成實例2的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例3
除了使用合成實例3的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例4
除了使用合成實例4的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例5
除了使用合成實例5的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例6
除了使用合成實例6的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例7
除了使用合成實例7的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例8
除了使用合成實例8的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例9
除了使用合成實例9的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
實例10
除了使用合成實例10的化合物代替合成實例1的化合物以
外,根據與實例1相同的方法製備硬罩幕組成物。
比較例1
除了使用合成比較例1的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
比較例2
除了使用合成比較例2的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
比較例3
除了使用合成比較例3的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
比較例4
除了使用合成比較例4的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
比較例5
除了使用合成比較例5的化合物代替合成實例1的化合物以外,根據與實例1相同的方法製備硬罩幕組成物。
評估
評估1:抗蝕刻性
在矽晶圓上將實例1到實例10以及比較例1到比較例5的每種硬罩幕組成物(化合物含量:12重量%到15重量%)旋塗到4,000埃厚,並且於400℃下在熱板上熱處理2分鐘,形成薄膜。
接著,測量薄膜的厚度。隨後,在分別用CHF3/CF4混合氣體以及N2/O2混合氣體乾式蝕刻薄膜100秒以及60秒之後,再
次測量薄膜的厚度。使用乾式蝕刻之前與之後薄膜的厚度以及其蝕刻時間,根據以下計算方程式1,計算塊體蝕刻速率(bulk etch rate,BER)。
[計算方程式1]
(初始薄膜厚度-蝕刻後的薄膜厚度)/蝕刻時間(埃/秒)
結果提供於表1中。
參考表1,分別由根據實例1到實例10的硬罩幕組成物形成的薄膜對蝕刻氣體具有足夠的抗蝕刻性,並且與分別由根據
比較例1到比較例5的硬罩幕組成物形成的薄膜相比,顯示改良的塊體蝕刻特徵。
評估2:平面化特徵和間隙填充特徵
在經圖案化的矽晶圓上將根據實例1到實例10以及比較例1到比較例5的每種硬罩幕組成物旋塗到2000埃厚,並且在400℃下烘烤120秒,形成薄膜。
藉由用場發射掃描電子顯微鏡(field emission scanning electron microscope,FE-SEM)檢查圖案的截面上是否存在空隙,評估間隙填充特徵。藉由用由K-MAC製造的薄膜厚度計測量圖案周圍的薄膜的厚度來評估平面化特徵,並且隨後根據圖1中所示的計算方程式2計算平面化特徵。本文中,h1與h2之間的較大差值表示較佳的平面化。
結果提供於表2中。
參考表2,與分別由根據比較例1到比較例5的硬罩幕組成物形成的薄膜相比,分別由根據實例1到實例10的硬罩幕組成物形成的薄膜顯示改良的間隙填充和平面化特徵。
雖然已經結合目前視為實用例示性實施例的內容來描述本發明,但應理解本發明不限於所揭露的實施例,而是相反,本發明意欲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佈置。
Claims (15)
- 一種聚合物,包括由以下化學式1表示的部分:
- 如申請專利範圍第1項所述的聚合物,其中在所述族群2中,X1以及X2獨立地是衍生自以下族群3所列化合物中的一者的二價基團:
- 如申請專利範圍第1項所述的聚合物,其中在所述族群2中,Y1以及Y2獨立地是衍生自以下族群3所列化合物中的一者的單價基團:
- 如申請專利範圍第1項所述的聚合物,其中在所述族群2中,X2、Y1以及Y2中的至少一者是衍生自經取代或未經取代的苯、經取代或未經取代的萘、經取代或未經取代的聯苯、經取代或未經取代的芘、經取代或未經取代的苝、經取代或未經取代的苯並苝、經取代或未經取代的蔻或其組合的基團。
- 如申請專利範圍第1項所述的聚合物,其中在所述族群1中,R1、R2以及R3獨立地是氫或經取代或未經取代的苯基。
- 如申請專利範圍第1項所述的聚合物,所述聚合物是由以下化學式2-1到化學式2-7以及化學式2-9中的一者表示:
- 如申請專利範圍第1項所述的聚合物,其重量平均分子量是1,000到200,000。
- 一種有機層組成物,包括如申請專利範圍第1到7項中的一項所述的聚合物,以及溶劑。
- 如申請專利範圍第8項所述的有機層組成物,其中以所述有機層組成物的總量計,所述聚合物以0.1重量%到30重量%的量被包含在內。
- 一種有機層,藉由固化如申請專利範圍第8項所述的有機層組成物而形成。
- 如申請專利範圍第10項所述的有機層,其中所述有機層包括硬罩幕層。
- 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8項所述的有機層組成物,熱處理所述有機層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,使所述光阻層曝光並且顯影以形成光阻圖案,使用所述光阻圖案選擇性地移除所述含矽薄層以及所述硬罩幕層以使一部分所述材料層暴露,以及蝕刻所述材料層的暴露部分。
- 如申請專利範圍第12項所述的形成圖案的方法,其中使用旋塗法塗覆所述有機層組成物。
- 如申請專利範圍第12項所述的形成圖案的方法,其中形成所述有機層的製程包括100℃到500℃下的熱處理。
- 如申請專利範圍第12項所述的形成圖案的方法,其進一步包括在形成所述光阻層之前形成底部抗反射塗層。
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