TW202128671A - 包含雜環化合物之阻劑下層膜形成組成物 - Google Patents
包含雜環化合物之阻劑下層膜形成組成物 Download PDFInfo
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- TW202128671A TW202128671A TW109134709A TW109134709A TW202128671A TW 202128671 A TW202128671 A TW 202128671A TW 109134709 A TW109134709 A TW 109134709A TW 109134709 A TW109134709 A TW 109134709A TW 202128671 A TW202128671 A TW 202128671A
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- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
提供一種具有特別高的乾式蝕刻速度的阻劑下層膜、該阻劑下層膜形成組成物、阻劑圖型形成方法及半導體裝置的製造方法。一種阻劑下層膜形成組成物,包含:含環氧基的化合物與雜環化合物的反應生成物、及溶劑,其中,該雜環化合物包含一個與環氧基具有反應性的部位。上述雜環化合物中所包含的雜環係以選自呋喃、吡咯、吡喃、咪唑、吡唑、噁唑、噻吩、噻唑、噻二唑、咪唑啶、噻唑烷、咪唑啉、二噁烷、嗎福啉、二嗪、噻嗪、***、四唑、二氧戊環、噠嗪、嘧啶、吡嗪、哌啶、哌嗪、吲哚、嘌呤、喹啉、異喹啉、
Description
本發明為關於一種具有特別高的乾式蝕刻速度的阻劑下層膜形成組成物、使用該阻劑下層膜形成組成物的阻劑下層膜及其製造方法、阻劑圖型的形成方法及半導體裝置的製造方法。
將阻劑膜進行曝光之際,反射波會有對該阻劑膜帶來不良影響之情形。為了抑制此情形之目的而所形成的阻劑下層膜亦被稱為抗反射膜。
阻劑下層膜係要求著,藉由塗佈溶液狀的阻劑下層膜形成用組成物、並使其硬化,而可容易地進行成膜。因此,該組成物必需含有藉由加熱等而可容易硬化之同時,對指定溶劑之溶解性為高的化合物(聚合物)。
形成於阻劑下層膜上的阻劑圖型,係以與基板垂直的方向的剖面形狀為矩形狀(即,無底切(undercut)、底部拉引等的直線(straight)的底部形狀)為宜。例如,若阻劑圖型成為底切形狀或底部拉引形狀時,會產生阻劑圖型的崩壞,於微影步驟之際,無法將被加工物(基板、絕緣膜等)加工成所期望的形狀或尺寸之類的問題。
又,對阻劑下層膜要求著,乾式蝕刻速度大於上層的阻劑膜(亦即,乾式蝕刻速度的選擇比較大)。
專利文獻1中揭示一種阻劑下層膜形成組成物,其使用主鏈中具有二硫鍵(disu1fide bond)的聚合物。專利文獻2中揭示一種具有縮水甘油酯基的環氧化合物。專利文獻3中揭示一種抗反射膜形成組成物,其特徵為包含:具有羥烷基構造作為氮原子上的取代基的三嗪三酮化合物、低聚物化合物或高分子化合物。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本再表2009-096340號公報
[專利文獻2]日本特開平8-81461號公報
[專利文獻3]日本再表2004-034148號公報
[發明所欲解決之課題]
於半導體元件的製造中,仍然要求著具有高乾式蝕刻速度的阻劑下層膜。為了製成具有高乾式蝕刻速度的阻劑下層膜,已知有將包含雜原子者適用於組成物的聚合物中之情形。
本申請案的發明人經深入研究之結果發現,將含環氧基的化合物與雜環化合物的反應生成物適用於阻劑下層膜形成組成物中時,將可達成相較於以往技術為更高的蝕刻速率化,其中,該含環氧基的化合物較佳為含縮水甘油酯基的化合物、較佳為具有縮水甘油酯基的含氮雜環化合物(異三聚氰酸(isocyanuric acid)等),該雜環化合物包含一個與環氧基具有反應性的部位。
本發明為有鑑於解決如此般之課題而完成的發明,目的為提供一種具有特別高的乾式蝕刻速度的阻劑下層膜形成組成物。又,本發明的目的亦為提供使用該阻劑下層膜形成組成物的阻劑下層膜及其製造方法、阻劑圖型的形成方法、及半導體裝置的製造方法。
[解決課題之手段]
本發明包含以下之內容。
[1].
一種阻劑下層膜形成組成物,包含:含環氧基的化合物與雜環化合物的反應生成物、及溶劑,其中,該雜環化合物包含一個與環氧基具有反應性的部位。
[2].
如[1]之阻劑下層膜形成組成物,其中,上述雜環化合物中所包含的雜環係選自呋喃、吡咯、吡喃、咪唑、吡唑、噁唑、噻吩、噻唑、噻二唑、咪唑啶、噻唑烷(thiazolidine)、咪唑啉、二噁烷、嗎福啉、二嗪、噻嗪、***、四唑、二氧戊環(dioxolane)、噠嗪、嘧啶、吡嗪、哌啶、哌嗪、吲哚、嘌呤、喹啉、異喹啉、啶、苯并吡喃、噻蒽、吩噻嗪(phenothiazine)、吩噁嗪(phenoxazine)、呫噸、吖啶、吩嗪(phenazine)及咔唑。
[3].
如[1]或[2]之阻劑下層膜形成組成物,其中,與環氧基具有反應性的部位係選自羥基、硫醇基、胺基、醯亞胺基及羧基。
[4].
如請求項1~3中任一項之阻劑下層膜形成組成物,其中,上述含環氧基的化合物係下述式(1)所表示的化合物。
(式(1)中,X為下述式(2)、式(3)或式(4)所表示的二價有機基,n1
、n2
各自獨立表示1至10的整數)
(式(2)、式(3)及式(4)中,
R1
及R2
各自獨立表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數2至10的烯基、可被氧原子或硫原子中斷的碳原子數2至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基及碳原子數1至6的烷硫基所成之群組之至少1個的一價官能基所取代。
R3
表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數3至10的烯基、可被氧原子或硫原子中斷的碳原子數3至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基、碳原子數1至6的烷硫基及下述式(5)所表示的有機基所成之群組之至少1個的一價官能基所取代)
(式(5)中,n3表示1至10的整數)。
[5].
如[1]~[4]中任一之阻劑下層膜形成組成物,其中,進而包含選自由交聯劑、交聯觸媒及界面活性劑所成之群組之至少一種。
[6].
一種阻劑下層膜,特徵在於,其係含有如[1]~[5]中任一項之阻劑下層膜形成組成物所成之塗佈膜的燒成物。
[7].
一種經圖型化的基板的製造方法,包含下述之步驟:
將如[1]~[5]中任一項之阻劑下層膜形成組成物塗佈在半導體基板上並進行烘烤來形成阻劑下層膜之步驟;
將阻劑塗佈在前述阻劑下層膜上並進行烘烤來形成阻劑膜之步驟;
將被覆有前述阻劑下層膜與前述阻劑的半導體基板進行曝光之步驟;
將曝光後的前述阻劑膜進行顯影並圖型化之步驟。
[8].
一種半導體裝置的製造方法,其特徵為包含下述之步驟:
在半導體基板上形成含有如[1]~[5]中任一項之阻劑下層膜形成組成物所成之阻劑下層膜之步驟;
在前述阻劑下層膜之上形成阻劑膜之步驟;
藉由對於阻劑膜照射光或電子線及之後的顯影來形成阻劑圖型之步驟;
藉由隔著所形成的前述阻劑圖型將前述阻劑下層膜進行蝕刻,來形成經圖型化的阻劑下層膜之步驟;及
藉由經圖型化的前述阻劑下層膜來加工半導體基板之步驟。
[9].
一種下述式(1)所表示的化合物與雜環化合物的反應生成物,其中,該雜環化合物包含一個與環氧基具有反應性的部位。
(式(1)中,X為下述式(2)、式(3)或式(4)所表示的二價有機基,n1
、n2
各自獨立表示1至10的整數)
(式(2)、式(3)及式(4)中,
R1
及R2
各自獨立表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數2至10的烯基、可被氧原子或硫原子中斷的碳原子數2至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基及碳原子數1至6的烷硫基所成之群組之至少1個的一價官能基所取代。
R3
表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數3至10的烯基、可被氧原子或硫原子中斷的碳原子數3至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基、碳原子數1至6的烷硫基及下述式(5)所表示的有機基所成之群組之至少1個的一價官能基所取代)
(式(5)中,n3表示1至10的整數)。
[發明的效果]
本發明的阻劑下層膜形成組成物,具有高的乾式蝕刻速度,故可解決因阻劑膜厚的薄膜化所造成的各種問題,而可達成更微細的半導體基板的微細加工。
[實施發明之最佳形態]
<阻劑下層膜形成組成物、含環氧基的化合物、包含一個與環氧基具有反應性的部位的雜環化合物、該含環氧基的化合物與雜環化合物的反應生成物>
本申請案的阻劑下層膜形成組成物,包含:含環氧基的化合物與雜環化合物的反應生成物、及溶劑,其中,該雜環化合物包含一個與環氧基具有反應性的部位。
上述含環氧基的化合物,只要是能達成上述目的之化合物即可並無限定,較佳為含縮水甘油酯基的化合物、較佳為具有縮水甘油酯基的含氮雜環化合物(異三聚氰酸等)。
上述含環氧基的化合物,可以是例如碳原子數6~40的包含芳香環構造的化合物、包含三嗪酮(triazineone)的化合物、包含三嗪二酮(triazinedione)的化合物或包含三嗪三酮(triazinetrione)的化合物,以包含三嗪三酮的化合物為較佳。
上述含環氧基的化合物係以下述式(1)所表示的化合物為較佳。
(式(1)中,X為下述式(2)、式(3)或式(4)所表示的二價有機基,n1
、n2
各自獨立表示1至10的整數)
(式(2)、式(3)及式(4)中,
R1
及R2
各自獨立表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數2至10的烯基、可被氧原子或硫原子中斷的碳原子數2至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基及碳原子數1至6的烷硫基所成之群組之至少1個的一價官能基所取代。
R3
表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數3至10的烯基、可被氧原子或硫原子中斷的碳原子數3至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基、碳原子數1至6的烷硫基及下述式(5)所表示的有機基所成之群組之至少1個的一價官能基所取代)
(式(5)中,n3表示1至10的整數)。
作為碳原子數1至10的烷基,可舉出甲基、乙基、n-丙基、i-丙基、環丙基、n-丁基、i-丁基、s-丁基、t-丁基、環丁基、1-甲基-環丙基、2-甲基-環丙基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、環戊基、1-甲基-環丁基、2-甲基-環丁基、3-甲基-環丁基、1,2-二甲基-環丙基、2,3-二甲基-環丙基、1-乙基-環丙基、2-乙基-環丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基、1-乙基-2-甲基-n-丙基、環己基、1-甲基-環戊基、2-甲基-環戊基、3-甲基-環戊基、1-乙基-環丁基、2-乙基-環丁基、3-乙基-環丁基、1,2-二甲基-環丁基、1,3-二甲基-環丁基、2,2-二甲基-環丁基、2,3-二甲基-環丁基、2,4-二甲基-環丁基、3,3-二甲基-環丁基、1-n-丙基-環丙基、2-n-丙基-環丙基、1-i-丙基-環丙基、2-i-丙基-環丙基、1,2,2-三甲基-環丙基、1,2,3-三甲基-環丙基、2,2,3-三甲基-環丙基、1-乙基-2-甲基-環丙基、2-乙基-1-甲基-環丙基、2-乙基-2-甲基-環丙基及2-乙基-3-甲基-環丙基等。
作為碳原子數2至10的烯基,可舉出乙烯基、1-丙烯基、2-丙烯基、1-甲基-1-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-n-丙基乙烯基、1-甲基-1-丁烯基、1-甲基-2-丁烯基、1-甲基-3-丁烯基、2-乙基-2-丙烯基、2-甲基-1-丁烯基、2-甲基-2-丁烯基、2-甲基-3-丁烯基、3-甲基-1-丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1-i-丙基乙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-環戊烯基、2-環戊烯基、3-環戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、1-甲基-2-戊烯基、1-甲基-3-戊烯基、1-甲基-4-戊烯基、1-n-丁基乙烯基、2-甲基-1-戊烯基、2-甲基-2-戊烯基、2-甲基-3-戊烯基、2-甲基-4-戊烯基、2-n-丙基-2-丙烯基、3-甲基-1-戊烯基、3-甲基-2-戊烯基、3-甲基-3-戊烯基、3-甲基-4-戊烯基、3-乙基-3-丁烯基、4-甲基-1-戊烯基、4-甲基-2-戊烯基、4-甲基-3-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1-甲基-2-乙基-2-丙烯基、1-s-丁基乙烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、1-i-丁基乙烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、2-i-丙基-2-丙烯基、3,3-二甲基-1-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、1-n-丙基-1-丙烯基、1-n-丙基-2-丙烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-t-丁基乙烯基、1-甲基-1-乙基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基、1-i-丙基-1-丙烯基、1-i-丙基-2-丙烯基、1-甲基-2-環戊烯基、1-甲基-3-環戊烯基、2-甲基-1-環戊烯基、2-甲基-2-環戊烯基、2-甲基-3-環戊烯基、2-甲基-4-環戊烯基、2-甲基-5-環戊烯基、2-亞甲基-環戊基(2-methylene-cyclopentyl group)、3-甲基-1-環戊烯基、3-甲基-2-環戊烯基、3-甲基-3-環戊烯基、3-甲基-4-環戊烯基、3-甲基-5-環戊烯基、3-亞甲基-環戊基、1-環己烯基、2-環己烯基及3-環己烯基等。
作為碳原子數2至10的炔基,可舉出乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、4-甲基-1-戊炔基、3-甲基-1-戊炔基。
所謂的「可被氧原子或硫原子中斷」,係指例如上述烷基、烯基及炔基中所包含的碳原子被氧原子或硫原子取代之涵義。例如,當烷基中、烯基中及炔基中的某碳原子被氧原子取代時,將變成包含醚鍵;例如,當烷基中、烯基中及炔基中的某碳原子被硫原子取代時,則變成包含硫醚鍵。
作為碳原子數1至6的烷基,係上述碳原子數1至10的烷基中的「碳原子數為1至6的烷基」。
作為鹵素原子,可舉出氟、氯、溴、及碘。
作為碳原子數1至10的烷氧基,可舉出甲氧基、乙氧基、n-丙氧基、i-丙氧基、n-丁氧基、i-丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、1-甲基-n-丁氧基、2-甲基-n-丁氧基、3-甲基-n-丁氧基、1,1-二甲基-n-丙氧基、1,2-二甲基-n-丙氧基、2,2-二甲基-n-丙氧基、1-乙基-n-丙氧基、n-己氧基、1-甲基-n-戊氧基、2-甲基-n-戊氧基、3-甲基-n-戊氧基、4-甲基-n-戊氧基、1,1-二甲基-n-丁氧基、1,2-二甲基-n-丁氧基、1,3-二甲基-n-丁氧基、2,2-二甲基-n-丁氧基、2,3-二甲基-n-丁氧基、3,3-二甲基-n-丁氧基、1-乙基-n-丁氧基、2-乙基-n-丁氧基、1,1,2-三甲基-n-丙氧基、1,2,2,-三甲基-n-丙氧基、1-乙基-1-甲基-n-丙氧基、及1-乙基-2-甲基-n-丙氧基等。
作為碳原子數1至6的烷硫基,可舉出乙硫基、丁硫基、己硫基等。
前述式(1)中,X係較佳以式(4)所表示。
前述式(1)中較佳如下:X以式(4)所表示,n1及n2為1,R3
為可被氧原子中斷的碳原子數1至5的烷基。此情形時,作為碳原子數1至5的烷基之具體例,係上述碳原子數1至10的烷基中的「碳原子數為1至5的烷基」。
前述式(1)中較佳為下述式(A-1)、式(A-7)或式(A-19)所表示的化合物:X以式(4)所表示,n1及n2為1,R3
為甲基、甲氧基甲基或以式(5)所表示,n3為1。
本申請案的式(1)所表示的化合物,可示例例如下述式(A-1)至(A-21),但並非被限定於該等。
上述含環氧基的化合物,可選自下述的化合物(a)~(s)。於式(o)中,R0
表示碳原子數1~10的伸烷基。
又,作為含環氧基的化合物,亦可以是下述所表示的包含三個以上的環氧基的化合物。作為具體例,可舉出縮水甘油醚化合物、縮水甘油酯化合物、縮水甘油胺化合物、含縮水甘油基的三聚異氰酸酯(isocyanurate)。作為使用於本申請案發明的含環氧基的化合物,可示例下述式(A0-1)~(A0-13)。
式(A0-1)係能以日產化學(股)製、商品名TEPIC-G、TEPIC-S、TEPIC-SS、TEPIC-HP、TEPIC-L(皆為異三聚氰酸1,3,5-參(2,3-環氧丙基)酯)來取得。
式(A0-2)係能以日產化學(股)製、商品名TEPIC-VL來取得。
式(A0-3)係能以日產化學(股)製、商品名TEPIC-FL來取得。
式(A0-4)係能以日產化學(股)製、商品名TEPIC-UC來取得。
式(A0-5)係能以Nagasechemtex(股)製、商品名Denaco1 EX-411來取得。
式(A0-6)係能以Nagasechemtex(股)製、商品名Denaco1 EX-521來取得。
式(A0-7)係能以Mitsubishi Gas Chemical(股)製、商品名TETRAD-X來取得。
式(A0-8)係能以昭和電工(股)製、商品名BATG來取得。
式(A0-9)係能以新日鐵住金化學(股)製、商品名YH-434L來取得。
式(A0-10)係能以旭有機材工業(股)製、商品名TEP-G來取得。
式(A0-11)係能以DIC(股)製、商品名EPICLON HP-4700來取得。
式(A0-12)係能以DAICEL(股)製、商品名EPOLEAD GT401來取得。尚,a、b、c、d係各別為0或1,a+b+c+d=1。
亦可使用以下的環氧化合物。
上述含環氧基的化合物、與雜環化合物(其包含一個與環氧基具有反應性的部位)的反應,可採用其本身習知的方法來進行。
上述雜環化合物係包含下述中記載的雜環的化合物。
上述雜環係以選自呋喃、吡咯、吡喃、咪唑、吡唑、噁唑、噻吩、噻唑、噻二唑、咪唑啶、噻唑烷、咪唑啉、二噁烷、嗎福啉、二嗪、噻嗪、***、四唑、二氧戊環、噠嗪、嘧啶、吡嗪、哌啶、哌嗪、吲哚、嘌呤、喹啉、異喹啉、啶、苯并吡喃、噻蒽、吩噻嗪、吩噁嗪、呫噸、吖啶、吩嗪及咔唑為較佳。
上述雜環的一部分的元素可被例如碳原子數1至5烷基、甲硫基等的取代基所取代。
該等之中,特別以選自可增加阻劑下層膜的乾式蝕刻速度的噻吩、四唑、噻唑及噻二唑之中為較佳。
上述與環氧基具有反應性的部位,較佳為選自羥基、硫醇基、胺基、醯亞胺基及羧基。
該等之中,特別以可增加阻劑下層膜的乾式蝕刻速度的羧基及硫醇基為較佳。
作為包含一個與環氧基具有反應性的部位的雜環化合物之具體例,可舉出下述所記載的化合物。
上述式(1)所表示的化合物的環氧基、與雜環化合物(其包含一個與環氧基具有反應性的部位)反應時,莫耳數的比例(即,前者:後者)為例如(0.1~1):1。較佳為(0.5~1):1。
等量反應以外的(剩餘的)環氧基,可與上述包含一個與環氧基具有反應性的部位的雜環化合物以外的化合物(例如,包含與環氧基具有反應性的部位的芳香族及/或脂肪族(芳香族羧酸、芳香族硫醇、脂肪族羧酸、芳香族硫醇、包含二個以上與環氧基具有反應性的部位的雜環化合物等))來進行反應。
上述包含與環氧基具有反應性的部位的化合物係可示例下述式(B-1)至(B-62),但並非被限定於該等。
本申請案的反應生成物的重量平均分子量(Mw)係例如300~4,000,400~3,000,或500~2,000。
[溶媒]
本發明的阻劑下層膜形成組成物係可藉由將上述各成分溶解於有機溶劑中來製造,並以均勻的溶液狀態來使用。
作為本發明相關的阻劑下層膜形成組成物的溶媒,只要是可溶解上述化合物、或該反應生成物的溶媒即可,可無特別限制地使用。特別是因為本發明相關的阻劑下層膜形成組成物係以均勻的溶液狀態來使用,若考慮其塗佈性能時,建議與於微影步驟中一般所使用的溶媒合併使用。
作為前述有機溶劑,可舉出例如乙二醇單甲基醚、乙二醇單乙基醚、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、二乙二醇單甲基醚、二乙二醇單乙基醚、丙二醇、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單甲基醚乙酸酯、丙二醇丙基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、甲基異丁基酮、環戊酮、環己酮、環庚酮、4-甲基-2-戊醇、2-羥基異酪酸甲酯、2-羥基異酪酸乙酯、乙氧基乙酸乙酯、乙酸2-羥基乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯、丙酮酸甲酯、丙酮酸乙酯、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯、2-庚酮、甲氧基環戊烷、苯甲醚、γ-丁內酯、N-甲基吡咯烷酮、N,N-二甲基甲醯胺、及N,N-二甲基乙醯胺。該等的溶劑係可單獨或可組合2種以上來使用。
該等的溶媒之中,以丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、乳酸乙酯、乳酸丁酯、及環己酮等為較佳。特別是以丙二醇單甲基醚、丙二醇單甲基醚乙酸酯為較佳。
[交聯觸媒]
為了促進交聯反應,本發明的阻劑下層膜形成組成物能夠含有交聯觸媒來作為任意成分。作為該交聯觸媒,除了酸性化合物、鹼性化合物之外,可使用藉由熱而產生酸或鹼的化合物。作為酸性化合物係可使用磺酸化合物或羧酸化合物,作為藉由熱而產生酸的化合物係可使用熱酸產生劑。
作為磺酸化合物或羧酸化合物,可舉出例如苯酚磺酸、p-甲苯磺酸、三氟甲烷磺酸、吡啶鎓三氟甲烷磺酸酯、吡啶鎓-p-甲苯磺酸酯(吡啶鎓-p-苯酚磺酸)、水楊酸、樟腦磺酸、5-磺柳酸、4-氯苯磺酸、4-羥基苯磺酸、吡啶鎓-4-羥基苯磺酸、苯二磺酸、1-萘磺酸、4-硝基苯磺酸、檸檬酸、苯甲酸、羥基苯甲酸。
作為熱酸產生劑,可舉出例如K-PURE[註冊商標]CXC-1612、同CXC-1614、同TAG-2172、同TAG-2179、同TAG-2678、同TAG2689(以上為King Industries公司製)、及SI-45、SI-60、SI-80、SI-100、SI-110、SI-150(以上為三新化學工業股份有限公司製)。
該等交聯觸媒係可組合1種或2種以上來使用。又,作為鹼性化合物係可使用胺化合物或氫氧化銨化合物,作為藉由熱而產生鹼的化合物係可使用脲。
作為胺化合物,可舉出例如三乙醇胺、三丁醇胺、三甲基胺、三乙基胺、三正丙基胺、三異丙基胺、三正丁基胺、三-tert-丁基胺、三正辛基胺、三異丙醇胺、苯基二乙醇胺、硬脂基二乙醇胺、及二氮雜雙環辛烷等的第3級胺、吡啶及4-二甲胺基吡啶等的芳香族胺。又,作為胺化合物,亦可舉出苄胺及正丁基胺等的第1級胺、二乙基胺及二正丁基胺等的第2級胺。該等的胺化合物係可單獨或組合二種以上來使用。
作為氫氧化銨化合物,可舉出例如氫氧化四甲基銨、氫氧化四乙基銨、氫氧化四丙基銨、氫氧化四丁基銨、氫氧化苄基三甲基銨、氫氧化苄基三乙基銨、氫氧化乙醯基三甲基銨、氫氧化苯基三甲基銨、氫氧化苯基三乙基銨。
又,作為藉由熱而產生鹼的化合物,可使用例如具有醯胺基、胺基甲酸酯基或氮丙啶基之類的熱不穩定性基,且藉由加熱而生成胺的化合物。作為藉由熱而產生鹼的化合物,其他亦可舉出脲、苄基三甲基氯化銨、苄基三乙基氯化銨、苄基二甲基苯基氯化銨、苄基十二烷基二甲基氯化銨、苄基三丁基氯化銨、氯化膽鹼。
當前述阻劑下層膜形成組成物包含交聯觸媒時,相對於阻劑下層膜形成組成物的全體固體成分,該含有量為0.0001~20質量%,較佳為0.01~15質量%,更佳為0.1~10質量%。
上述之中,以酸性化合物及/或藉由熱而產生酸的化合物(交聯酸觸媒)為較佳。
[交聯劑]
本發明的阻劑下層膜形成組成物可包含交聯劑成分。作為該交聯劑,可舉出三聚氰胺系、取代脲系、或此等的聚合物系等。較佳為具有至少2個交聯形成取代基的交聯劑,如有甲氧基甲基化甘脲(glycoluril)(例如四甲氧基甲基甘脲)、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、或甲氧基甲基化硫脲等的化合物。又,亦可使用該等的化合物的縮合體。
該等之中,以甲氧基甲基化甘脲(例如四甲氧基甲基甘脲)為較佳。
又,作為上述交聯劑,可使用耐熱性為高的交聯劑。作為耐熱性為高的交聯劑,可使用分子內包含具有芳香族環(例如苯環、萘環)的交聯形成取代基的化合物。
該化合物係可舉出具有下述式(5-1)的部分構造的化合物、或具有下述式(5-2)的重複單位的聚合物或低聚物。
上述R11
、R12
、R13
、及R14
為氫原子或碳原子數1~10的烷基。m1、m2、m3及m4分別代表0~3的整數。作為碳原子數1~10的烷基,可舉出甲基、乙基、n-丙基、i-丙基、環丙基、n-丁基、i-丁基、s-丁基、t-丁基、環丁基、1-甲基-環丙基、2-甲基-環丙基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、環戊基、1-甲基-環丁基、2-甲基-環丁基、3-甲基-環丁基、1,2-二甲基-環丙基、2,3-二甲基-環丙基、1-乙基-環丙基、2-乙基-環丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基、1-乙基-2-甲基-n-丙基、環己基、1-甲基-環戊基、2-甲基-環戊基、3-甲基-環戊基、1-乙基-環丁基、2-乙基-環丁基、3-乙基-環丁基、1,2-二甲基-環丁基、1,3-二甲基-環丁基、2,2-二甲基-環丁基、2,3-二甲基-環丁基、2,4-二甲基-環丁基、3,3-二甲基-環丁基、1-n-丙基-環丙基、2-n-丙基-環丙基、1-i-丙基-環丙基、2-i-丙基-環丙基、1,2,2-三甲基-環丙基、1,2,3-三甲基-環丙基、2,2,3-三甲基-環丙基、1-乙基-2-甲基-環丙基、2-乙基-1-甲基-環丙基、2-乙基-2-甲基-環丙基及2-乙基-3-甲基-環丙基等。
分別滿足m1為1≦m1≦6-m2,m2為1≦m2≦5,m3為1≦m3≦4-m2,m4為1≦m4≦3。
式(5-1)及式(5-2)的化合物、聚合物、低聚物,可示例如下述。
上述化合物係能以旭有機材工業(股)、本州化學工業(股)的製品來取得。例如上述交聯劑之中,式(6-22)的化合物係能以旭有機材工業(股)、商品名TMOM-BP來取得。
依照使用的塗佈溶劑、使用的基底基板、要求的溶液黏度、要求的膜形狀等,而交聯劑的添加量會有所變動,相對於阻劑下層膜形成組成物的全體固體成分,交聯劑的添加量為0.001~80質量%,較佳為0.01~50質量%,更佳為0.1~40質量%。該等交聯劑亦有因為自縮合而引起交聯反應之情形,當本發明的上述的聚合物中存在交聯性取代基時,則能夠引起與此等的交聯性取代基的交聯反應。
[界面活性劑]
為了提升對於半導體基板的塗佈性,本發明的阻劑下層膜形成組成物可含有界面活性劑來作為任意成分。作為前述界面活性劑,可舉出例如聚氧乙烯月桂醚、聚氧乙烯硬脂基醚、聚氧乙烯鯨蠟醚、聚氧乙烯油基醚等的聚氧乙烯烷基醚類、聚氧乙烯辛基苯基醚、聚氧乙烯壬基苯基醚等的聚氧乙烯烷基芳基醚類、聚氧乙烯·聚氧丙烯嵌段共聚合物類、去水山梨醇單月桂酸酯、去水山梨醇單棕櫚酸酯、去水山梨醇單硬脂酸酯、去水山梨醇單油酸酯、去水山梨醇三油酸酯、去水山梨醇三硬脂酸酯等的去水山梨醇脂肪酸酯類、聚氧乙烯去水山梨醇單月桂酸酯、聚氧乙烯去水山梨醇單棕櫚酸酯、聚氧乙烯去水山梨醇單硬脂酸酯、聚氧乙烯去水山梨醇三油酸酯、聚氧乙烯去水山梨醇三硬脂酸酯等的聚氧乙烯去水山梨醇脂肪酸酯類等的非離子系界面活性劑、F-Top[註冊商標]EF301、同EF303、同EF352(Mitsubishi Materials E1ectronic Chemicals股份有限公司製)、MEGAFACE[註冊商標]F171、同F173、同R-30、同R-30N、同R-40、同R-40-LM(DIC股份有限公司製)、F1uorad FC430、同FC431(住友3M股份有限公司製)、AashiGuard[註冊商標]AG710、Surf1on[註冊商標]S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(旭硝子股份有限公司製)等的氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業股份有限公司製)。該等的界面活性劑係可單獨或組合二種以上來使用。當前述阻劑下層膜形成組成物包含界面活性劑時,相對於阻劑下層膜形成組成物的全體固體成分,該含有量為0.0001~10質量%,較佳為0.01~5質量%。
本發明相關的阻劑下層膜形成組成物的固體成分,通常為0.1~70質量%,較佳設為0.1~60質量%。固體成分係從阻劑下層膜形成組成物中去除溶媒後而得的全成分的含有比例。固體成分中的本申請案的化合物或反應生成物的比例,以1~100質量%、1~99.9質量%、50~99.9質量%、50~95質量%、50~90質量%之順序為較佳。
[其他的成分]
本發明的阻劑下層膜形成組成物中可添加吸光劑、流變調整劑、接著補助劑等。流變調整劑對於提升阻劑下層膜形成組成物的流動性為有效。接著補助劑對於提升半導體基板或阻劑與下層膜的密著性為有效。
作為吸光劑係可適合使用例如「工業用色素的技術與市場」(CMC出版)或「染料便覽」(有機合成化學協會編)記載的市售的吸光劑、例如C.I.Disperse Ye11ow 1, 3,4,5,7,8,13,23,31,49,50,51,54,60,64,66,68,79,82,88,90,93, 102,114及124;C.I.Disperse Orange1, 5,13,25,29,30,31,44, 57,72及73;C.I.Disperse Red 1,5,7,13,17,19,43,50,54,58, 65,72,73,88,117,137,143,199及210;C.I.Disperse Vio1et 43;C.I.Disperse B1ue 96;C.I.F1uorescent Brightening Agent 112,135及163;C.I.So1vent Orange2及45;C.I. So1vent Red 1,3,8,23,24,25,27及49;C.I.Pigment Green 10;C.I.Pigment Brown 2等。相對於阻劑下層膜形成組成物的全體固體成分,上述吸光劑通常為10質量%以下,較佳以5質量%以下的比例來進行調配。
主要是提升阻劑下層膜形成組成物的流動性,特別是於烘烤步驟中,為了提升阻劑下層膜的膜厚均勻性或提高阻劑下層膜形成組成物對孔洞內部的填充性之目的下,而添加流變調整劑。作為具體例,可舉出鄰苯二甲酸二甲酯、鄰苯二甲酸二乙酯、鄰苯二甲酸二異丁酯、鄰苯二甲酸二己酯、鄰苯二甲酸丁基異癸酯等的鄰苯二甲酸衍生物、己二酸二正丁酯、己二酸二異丁酯、己二酸二異辛酯、己二酸辛癸酯等的己二酸衍生物、馬來酸二正丁酯、馬來酸二乙酯、馬來酸二壬酯等的馬來酸衍生物、油酸甲酯、油酸丁酯、油酸四氫呋喃酯等的油酸衍生物、或硬脂酸正丁酯、硬脂酸甘油酯等的硬脂酸衍生物。相對於阻劑下層膜形成組成物的全體固體成分,該等的流變調整劑係通常以未滿30質量%的比例來進行調配。
主要是提升基板或阻劑與阻劑下層膜形成組成物的密著性,特別是於顯影時,以防止阻劑的剝離之目的下,而添加接著補助劑。作為具體例,可舉出三甲基氯矽烷、二甲基羥甲基氯矽烷、甲基二苯基氯矽烷、氯甲基二甲基氯矽烷等的氯矽烷類、三甲基甲氧基矽烷、二甲基二乙氧基矽烷、甲基二甲氧基矽烷、二甲基羥甲基乙氧基矽烷、二苯基二甲氧基矽烷、苯基三乙氧基矽烷等的烷氧基矽烷類、六甲基二矽氮烷、N,N’-雙(三甲基矽基)脲、二甲基三甲基矽基胺、三甲基矽基咪唑等的矽氮烷類、羥甲基三氯矽烷、γ-氯丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三甲氧基矽烷等的矽烷類、苯并***、苯并咪唑、吲唑、咪唑、2-巰基苯并咪唑、2-巰基苯并噻唑、2-巰基苯并噁唑、脲唑、硫尿嘧啶、巰基咪唑、巰基嘧啶等的雜環式化合物或、1,1-二甲基脲、1,3-二甲基脲等的脲、或硫脲化合物。相對於阻劑下層膜形成組成物的全體固體成分,該等的接著補助劑通常為未滿5質量%,較佳以未滿2質量%的比例來進行調配。
[阻劑下層膜、經圖型化的基板的製造方法及半導體裝置的製造方法]
以下,對於使用本發明相關的阻劑下層膜形成組成物所製造的阻劑下層膜、經圖型化的基板的製造方法及半導體裝置的製造方法來進行說明。
(阻劑下層膜)
本發明相關的阻劑下層膜,可藉由將上述的阻劑下層膜形成組成物塗佈至半導體基板上並進行燒成來製造。
作為塗佈本發明的阻劑下層膜形成組成物的半導體基板,可舉出例如矽晶圓、鍺晶圓、及砷化鎵、磷化銦、氮化鎵、氮化銦、氮化鋁等的化合物半導體晶圓。
當使用在表面上形成有無機膜的半導體基板時,該無機膜係可藉由例如ALD(原子層沉積)法、CVD(化學氣相沉積)法、反應性濺鍍法、離子蒸鍍法、真空蒸鍍法、旋轉塗佈法(旋塗玻璃:SOG)來形成。作為前述無機膜,可舉出例如多晶矽膜(po1ysi1icon)、氧化矽膜、氮化矽膜、BPSG(Boro-Phospho Si1icate G1ass)膜、氮化鈦膜、氮化氧化鈦膜、鎢膜、氮化鎵膜、及砷化鎵膜。
藉由旋轉器、塗佈機等的適當的塗佈方法,在如此般的半導體基板上塗佈本發明的阻劑下層膜形成組成物。之後,藉由使用加熱板等的加熱方法進行烘烤來形成阻劑下層膜。作為烘烤條件,可從烘烤溫度100℃~400℃、烘烤時間0.3分鐘~60分鐘之中來適當地選擇。較佳為烘烤溫度120℃~350℃、烘烤時間0.5分鐘~30分鐘,又較佳為烘烤溫度150℃~300℃、烘烤時間0.8分鐘~10分鐘。
作為所形成的阻劑下層膜的膜厚,例如為0.001μm(1nm)~10μm,較佳為0.002μm(2nm)~1μm,又較佳為0.005μm(5nm)~0.5μm(500nm)。當烘烤時的溫度低於上述範圍的話,交聯會變得不足。另一方面,當烘烤時的溫度高於上述範圍的話,阻劑下層膜會有因熱而被分解之情形。
(經圖型化的基板的製造方法)
經圖型化的基板的製造方法為經過以下的步驟。通常是在阻劑下層膜之上形成並製造光阻劑層。作為採用其本身習知的方法在阻劑下層膜之上進行塗佈、燒成所形成的光阻劑,只要是對用於曝光時的光為能夠感光者即可,並無特別限定。負型光阻劑及正型光阻劑皆可使用。例如:含有酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所成之正型光阻劑;含有具有藉由酸分解而使鹼溶解速度上昇的基的黏合劑與光酸產生劑所成之化學增幅型光阻劑;含有具有藉由酸分解而使光阻劑的鹼溶解速度上昇的低分子化合物、鹼可溶性黏合劑與光酸產生劑所成之化學增幅型光阻劑;及含有具有藉由酸分解而使鹼溶解速度上昇的基的黏合劑、藉由酸分解而使光阻劑的鹼溶解速度的低分子化合物與光酸產生劑所成之化學增幅型光阻劑等。可舉出例如JSR(股)製商品名V146G、Ship1ey公司製商品名APEX-E、住友化學工業(股)製商品名PAR710、及信越化學工業(股)製商品名AR2772、SEPR430等。又,可舉出例如Proc.SPIE,Vo1.3999,330-334(2000)、Proc.SPIE,Vo1.3999, 357-364(2000)、或Proc.SPIE,Vo1.3999,365-374(2000)所記載般的含氟原子聚合物系光阻劑。
曝光係通過用來形成指定圖型的遮罩(網線)來進行,可使用例如i線、KrF準分子雷射、ArF準分子雷射、EUV(極端紫外線)或EB(電子線)。顯影係使用鹼顯影液,可從顯影溫度5℃~50℃、顯影時間10秒鐘~300秒鐘來適當地選擇。作為鹼顯影液,可使用例如氫氧化鈉、氫氧化鉀、碳酸鈉、矽酸鈉、偏矽酸鈉、氨水等的無機鹼類、乙基胺、n-丙基胺等的第一胺類、二乙基胺、二-n-丁基胺等的第二胺類、三乙基胺、甲基二乙基胺等的第三胺類、二甲基乙醇胺、三乙醇胺等的醇胺類、氫氧化四甲基銨、氫氧化四乙基銨、膽鹼等的第4級銨鹽、吡咯、哌啶等的環狀胺類等的鹼類的水溶液。進而亦可添加適當量的異丙醇等的醇類、非離子系等的界面活性劑至上述鹼類的水溶液中來使用。該等之中,較佳的顯影液為第四級銨鹽,更佳為氫氧化四甲基銨及膽鹼。進而亦可加入界面活性劑等至該等的顯影液中。亦可使用下述之方法:利用乙酸丁酯等的有機溶媒取代鹼顯影液來進行顯影,以將光阻劑的鹼溶解速度未被提升的部分進行顯影。經由上述步驟,可製造出上述阻劑為經圖型化的基板。
接下來,將形成的阻劑圖型作為遮罩,並進行前述阻劑下層膜的乾式蝕刻。此時,當使用的半導體基板的表面上形成有前述無機膜時,使該無機膜的表面露出,當使用的半導體基板的表面上未形成有前述無機膜時,則使該半導體基板的表面露出。之後,經過藉由基板其本身習知的方法(乾式蝕刻法等)來加工基板之步驟,而能夠製造半導體裝置。
[實施例]
本說明書之下述合成例中所表示的聚合物的重量平均分子量(Mw)係藉由凝膠滲透層析法(以下簡稱為GPC)之測量結果。測量係使用Tosoh(股)製GPC裝置,測量條件等係如同下述。
GPC管柱:Shodex[註冊商標]·Asahipak[註冊商標](昭和電工(股))
管柱溫度:40℃
溶媒:四氫呋喃(THF)
流量:0.35m1/min
標準樣品:聚苯乙烯(Tosoh(股))
(原料單體的合成)
<合成例1>
裝入根據美國專利第3230220號說明書的方法所合成的異三聚氰酸三羧基甲基酯(TAICA)38.70g、N-甲基-2-吡咯烷酮(關東化學(股)製)300.00g,烯丙基溴(東京化成工業(股)製)70.91g、碳酸鉀(關東化學(股)製)79.38g,並升溫至80-90℃。之後,進行反應2小時,並確認反應成為恆重。反應結束後,追加甲苯(關東化學(股)製)580.50g。進行過濾,並以水580.50g進行水洗3次。將有機層濃縮乾燥後,裝入乙醇(關東化學(股)製)387.00g,並以20-30℃攪拌30分鐘。攪拌結束後,進行過濾並乾燥所得到的結晶,以收率85.2%得到44.32g的式(A1-1)所表示的目標生成物(異三聚氰酸三烯丙基乙酸酯(triallyl acetate isocyanuric acid):TAAICA)。
<合成例2>
裝入合成例1所合成的TAAICA44.32g、氯仿(關東化學(股)製)443.20g,並加入m-氯過苯甲酸(東京化成工業(股)製)125.06g至其中。進行反應47小時。反應結束後,追加氯仿(關東化學(股)製)88.64g。進而,以5%碳酸氫鈉(關東化學(股)製)886.40g來進行洗淨。繼續以10%亞硫酸鈉(關東化學(股)製)443.20g、5%碳酸氫鈉(關東化學(股)製)886.40g來進行洗淨,進而以水443.20g進行洗淨2次。濃縮後,進行管柱純化。管柱純化後,以收率83.7%得到41.31g的式(A1-2)所表示的目標生成物(異三聚氰酸三縮水甘油基乙酸酯(triglycidyl acetate isocyanuric acid):
TAGICA)。
<合成例3>
將丙二醇單甲基醚42.05g加入至具有合成例2所得到的TAGICA5.00g、2-巰基-5-甲硫基-1,3,4-噻二唑5.22g、乙基三苯基溴化鏻0.41g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌23小時,得到相當於式(A1-3)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為1000。
<合成例4>
將丙二醇單甲基醚36.91g加入至具有合成例2所得到的TAGICA5.00g、2-巰基-1,3,4-噻二唑3.82g、乙基三苯基溴化鏻0.41g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌4小時,得到相當於式(A1-4)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為850。
<合成例5>
將丙二醇單甲基醚38.42g加入至具有合成例2所得到的TAGICA5.00g、2-巰基-5-甲基-1,3,4-噻二唑4.20g、乙基三苯基溴化鏻0.41g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌22小時,得到相當於式(A1-5)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為800。
<合成例6>
將丙二醇單甲基醚36.37g加入至具有合成例2所得到的TAGICA5.00g、5-巰基-1-甲基四唑3.69g、乙基三苯基溴化鏻0.41g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌24小時,得到相當於式(A1-6)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為800。
<合成例7>
將丙二醇單甲基醚37.89g加入至具有合成例2所得到的TAGICA5.00g、1H-四唑-1-乙酸4.07g、乙基三苯基溴化鏻0.41g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌24小時,得到相當於式(A1-7)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為850。
<合成例8>
裝入根據專利公報(WO2017/208910)記載的方法所合成的異三聚氰酸甲基酯(methylisocyanuric acid;Me-ICA)10.00g、碳酸鉀(關東化學(股)製)14.49g、氯乙酸烯丙酯(allyl chloroacetate;A1drich製)20.48g、N,N-二甲基甲醯胺(關東化學(股)製)40.00g,並以60℃攪拌25小時。裝入甲苯(關東化學(股)製)100.00g並進行過濾。將水100.00g加入至其中並以50℃進行分液。進而追加水100.00g至所得到的有機層中,並以50℃進行分液。藉由將所得到的有機層進行濃縮,以收率86.5%得到20.51g的式(B1-1)所表示的目標生成物(異三聚氰酸甲基二烯丙基乙酸酯(methyl diallyl acetate isocyanuric acid):Me-DAAICA)。
<合成例9>
裝入合成例8所得到的Me-DAAICA20.51g、氯仿(關東化學(股)製)153.83g,並添加m-氯過苯甲酸(東京化成工業(股)製)38.52g至其中。進行反應71小時,並確認反應成為恆重。反應結束後,追加氯仿(關東化學(股)製)205.10g、5重量%碳酸氫鈉(關東化學(股)製)410.20g。進行分液,並裝入10重量%亞硫酸鈉(關東化學(股)製)205.10g至所得到的有機層中。再次進行分液,並裝入5重量%碳酸氫鈉(關東化學(股)製)410.20g至所得到的有機層中。之後,進行分液,加入水205.10g至所得到的有機層中,並進行洗淨2次。將有機層濃縮乾燥後進行管柱純化,以收率46.6%得到10.46g的式(B1-2)所表示的目標生成物(異三聚氰酸甲基二縮水甘油基乙酸酯(methyl diglycidyl acetate isocyanuric acid):Me-DAGICA)。
<合成例10>
將丙二醇單甲基醚38.91g加入至具有合成例9所得到的Me-DAGICA5.00g、2-巰基-5-甲硫基-1,3,4-噻二唑4.60g、乙基三苯基溴化鏻0.13g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌23小時,得到相當於式(B1-3)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為600。
<合成例11>
將丙二醇單甲基醚38.02g加入至具有合成例2所得到的TAGICA5.00g、噻唑-4-羧酸4.10g、乙基三苯基溴化鏻0.41g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌24小時,得到相當於式(A1-8)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為1200。
<合成例12>
將丙二醇單甲基醚36.50g加入至具有合成例2所得到的TAGICA5.00g、2-巰基噻唑3.72g、乙基三苯基溴化鏻0.41g的反應燒瓶中,在氮環境下以105℃進行加熱攪拌24小時,得到相當於式(A1-9)的反應生成物。藉由GPC測量的以聚苯乙烯換算的重量平均分子量Mw為760。
(組成物調製)
[實施例1]
在包含合成例3所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[實施例2]
在包含合成例4所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[實施例3]
在包含合成例5所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[實施例4]
在包含合成例6所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[實施例5]
在包含合成例7所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[實施例6]
在包含合成例10所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[實施例7]
在包含合成例11所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[實施例8]
在包含合成例12所得到的反應生成物0.23g的溶液1.23g中,加入丙二醇單甲基醚29.70g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.06g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.001g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
[比較例1]
在包含根據WO2009/096340的合成例1記載的方法所得到的反應生成物0.72g的溶液3.58g中,加入丙二醇單甲基醚88.43g、丙二醇單甲基醚乙酸酯9.90g、四甲氧基甲基甘脲(日本Cytec Industries(股)、商品名:POWDERLINK[註冊商標]1174)0.18g、苯酚磺酸(東京化成工業(股))0.01g、及界面活性劑(DIC(股)、商品名:R-40)0.01g,來製成溶液。之後,使用孔徑0.02μm的聚乙烯製微濾器來進行過濾,並調製成阻劑下層膜形成用組成物。
(乾式蝕刻速度的測量)
藉由旋轉器,將實施例1~8及比較例1所調製的阻劑下層膜形成用組成物分別塗佈至矽晶圓上,在加熱板上以205℃烘烤1分鐘,形成各別膜厚100nm的阻劑下層膜。將該等使用Samco(股)製乾式蝕刻裝置(RIE-10NR),以使用CF4
作為乾式蝕刻氣體之條件下來測量乾式蝕刻速度(每單位時間的膜厚的減少量)。將由比較例1所得到的阻劑下層膜的蝕刻選擇比設為1.00時的各下層膜的蝕刻選擇比表示於表1。
由上述之結果可得知,相較於比較例1,實施例1~8具有充分高的蝕刻選擇性。其結果,藉由本發明所得到的阻劑下層膜形成用組成物係可縮短將阻劑下層膜進行乾式蝕刻時的蝕刻時間,於以乾式蝕刻去除阻劑下層膜之際,可抑制阻劑膜厚減少的不佳的現象。進而,可縮短乾式蝕刻時間,係指可抑制對於阻劑下層膜的基底基板為不佳的蝕刻損傷,故在作為阻劑下層膜為特別有用的。
(光學參數的評估)
旋轉塗佈機,將本說明書記載的實施例1~8及比較例1所調製的阻劑下層膜形成組成物分別塗佈(旋轉塗佈)至矽晶圓上。將塗佈後的矽晶圓在加熱板上以205℃、加熱1分鐘,形成阻劑下層膜形成組成物(膜厚30nm)。又,將該等的阻劑下層膜形成組成物使用分光橢圓偏光計(製品名:VUV-VASE VU-302、J.A.Woollam公司製),測量在波長193nm下的n值(折射率)及k值(衰減係數或吸光係數)。將光學參數的測量結果表示於表4。
本發明相關的阻劑下層膜形成組成物係提供具有特別高的乾式蝕刻速度的阻劑下層膜。
Claims (9)
- 一種阻劑下層膜形成組成物,包含:含環氧基的化合物與雜環化合物的反應生成物、及溶劑,其中,該雜環化合物包含一個與環氧基具有反應性的部位。
- 如請求項1或2之阻劑下層膜形成組成物,其中,與環氧基具有反應性的部位係選自羥基、硫醇基、胺基、醯亞胺基及羧基。
- 如請求項1~3中任一項之阻劑下層膜形成組成物,其中,上述含環氧基的化合物係下述式(1)所表示的化合物, (式(1)中,X為下述式(2)、式(3)或式(4)所表示的二價有機基,n1 、n2 各自獨立表示1至10的整數) (式(2)、式(3)及式(4)中, R1 及R2 各自獨立表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數2至10的烯基、可被氧原子或硫原子中斷的碳原子數2至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基及碳原子數1至6的烷硫基所成之群組之至少1個的一價官能基所取代, R3 表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數3至10的烯基、可被氧原子或硫原子中斷的碳原子數3至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基、碳原子數1至6的烷硫基及下述式(5)所表示的有機基所成之群組之至少1個的一價官能基所取代) (式(5)中,n3表示1至10的整數)。
- 如請求項1~4中任一項之阻劑下層膜形成組成物,其中,進而包含選自由交聯劑、交聯觸媒及界面活性劑所成之群組之至少一種。
- 一種阻劑下層膜,特徵在於,其係含有如請求項1~請求項5中任一項之阻劑下層膜形成組成物所成之塗佈膜的燒成物。
- 一種經圖型化的基板的製造方法,包含下述之步驟: 將如請求項1~請求項5中任一項之阻劑下層膜形成組成物塗佈在半導體基板上並進行烘烤來形成阻劑下層膜之步驟; 將阻劑塗佈在前述阻劑下層膜上並進行烘烤來形成阻劑膜之步驟; 將被覆有前述阻劑下層膜與前述阻劑的半導體基板進行曝光之步驟; 將曝光後的前述阻劑膜進行顯影並圖型化之步驟。
- 一種半導體裝置的製造方法,其特徵為包含下述之步驟: 在半導體基板上形成含有如請求項1~請求項5中任一項之阻劑下層膜形成組成物所成之阻劑下層膜之步驟; 在前述阻劑下層膜之上形成阻劑膜之步驟; 藉由對於阻劑膜照射光或電子線及之後的顯影來形成阻劑圖型之步驟; 藉由隔著所形成的前述阻劑圖型將前述阻劑下層膜進行蝕刻,來形成經圖型化的阻劑下層膜之步驟;及 藉由經圖型化的前述阻劑下層膜來加工半導體基板之步驟。
- 一種下述式(1)所表示的化合物與雜環化合物的反應生成物,其中,該雜環化合物包含一個與環氧基具有反應性的部位, (式(1)中,X為下述式(2)、式(3)或式(4)所表示的二價有機基,n1 、n2 各自獨立表示1至10的整數) (式(2)、式(3)及式(4)中, R1 及R2 各自獨立表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數2至10的烯基、可被氧原子或硫原子中斷的碳原子數2至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基及碳原子數1至6的烷硫基所成之群組之至少1個的一價官能基所取代, R3 表示氫原子、可被氧原子或硫原子中斷的碳原子數1至10的烷基、可被氧原子或硫原子中斷的碳原子數3至10的烯基、可被氧原子或硫原子中斷的碳原子數3至10的炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6的烷基、鹵素原子、碳原子數1至10的烷氧基、硝基、氰基、碳原子數1至6的烷硫基及下述式(5)所表示的有機基所成之群組之至少1個的一價官能基所取代) (式(5)中,n3表示1至10的整數)。
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