TWI748087B - 使用茀化合物之阻劑下層膜形成組成物 - Google Patents
使用茀化合物之阻劑下層膜形成組成物 Download PDFInfo
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- TWI748087B TWI748087B TW107113447A TW107113447A TWI748087B TW I748087 B TWI748087 B TW I748087B TW 107113447 A TW107113447 A TW 107113447A TW 107113447 A TW107113447 A TW 107113447A TW I748087 B TWI748087 B TW I748087B
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- 239000000203 mixture Substances 0.000 title claims abstract description 94
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- 235000021286 stilbenes Nutrition 0.000 title 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 3
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- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
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- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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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
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Abstract
本發明係提供兼具高蝕刻耐性、高耐熱性與良好塗佈性的阻劑下層膜形成組成物,使用該阻劑下層膜形成組成物之阻劑下層膜及其製造方法、阻劑圖型之形成方法、及半導體裝置之製造方法。 本發明之阻劑下層膜形成組成物,其特徵係包含 下述式(1) [式(1)中,表示單鍵或雙鍵,X1
表示-N(R1
)-、X2
表示-N(R2
)-、X3
表示-CH(R3
)-、X4
表示-CH(R4
)-等,R1
、R2
、R3
及R4
表示氫原子、C1~20之直鏈、支鏈或環狀之烷基等,R5
、R6
、R9
及R10
表示氫原子、羥基、烷基等,R7
及R8
表示苯環或萘環,n及o為0或1]表示之化合物或式(1)表示之化合物所衍生之聚合物。將該組成物塗佈於半導體基板上,進行燒成形成阻劑下層膜,其上任意選擇經由無機阻劑下層膜,形成阻劑膜,藉由光或電子束之照射與顯影,形成阻劑圖型,以阻劑圖型蝕刻下層膜,藉由圖型化後之下層膜,對半導體基板進行加工製造半導體裝置。
Description
本發明係有關兼具高蝕刻耐性、高耐熱性與良好塗佈性的阻劑下層膜形成組成物,使用該阻劑下層膜形成組成物之阻劑下層膜及其製造方法、阻劑圖型之形成方法、及半導體裝置之製造方法。
近年,作為阻劑下層膜之特性,被強力要求高蝕刻耐性或高耐熱性,由包含苯基萘基胺酚醛清漆樹脂之多層微影步驟用阻劑下層膜材料(專利文獻1)或由包含含有具伸芳基或雜環基之單位結構之聚合物的微影用阻劑下層膜形成組成物(專利文獻2)所製造的下層膜,具有其上以蒸鍍可形成硬遮罩之耐熱性,兼具作為抗反射膜之效果等的報告。 [先前技術文獻] [專利文獻]
[專利文獻1]WO2013/047516 [專利文獻2]WO2012/050064
[發明所欲解決之課題]
因伴隨阻劑圖型之微細化,所要求之阻劑層之薄膜化,而形成至少2層阻劑下層膜,以該阻劑下層膜作為遮罩材使用之微影步驟已為人知。此乃是在半導體基板上,設置至少一層之有機膜(下層有機膜)與、至少一層的無機下層膜,以形成於上層阻劑膜之阻劑圖型作為遮罩,將無機下層膜進行圖型化,以該圖型作為遮罩,進行下層有機膜之圖型化的方法,可形成高長寬比的圖型。作為前述形成至少2層的材料。可列舉有機樹脂(例如,丙烯酸樹脂、酚醛清漆樹脂)與無機系材料(矽樹脂(例如,有機聚矽氧烷)、無機矽化合物(例如,SiON、SiO2
)等)之組合。此外,近年,為了得到1個圖型時,廣泛使用進行2次微影與2次蝕刻之雙圖型化技術,在各自之步驟,使用了上述多層步驟。
此外,阻劑下層膜形成組成物,在半導體基板上,使用旋轉塗佈機塗佈、成膜,就生產性、經濟性的觀點為佳。這種塗佈型阻劑下層膜形成組成物,必須具有良好的塗佈性。
期待提供進一步改善上述較佳特性之阻劑下層膜的阻劑下層膜形成組成物。
本發明係基於這種課題解決而完成者,本發明之目的係提供兼具高蝕刻耐性、高耐熱性與良好塗佈性的阻劑下層膜形成組成物。又,本發明之目的係提供使用該阻劑下層膜形成組成物之阻劑下層膜及其製造方法、阻劑圖型之形成方法、及半導體裝置之製造方法。 [用以解決課題之手段]
本發明係提供包含賦予高蝕刻耐性、高耐熱性等之機能之新穎化合物的阻劑下層膜組成物,製作使用此組成物之阻劑下層膜,而達成上述的特性者。
本發明包含以下者。 [1]一種阻劑下層膜形成組成物,其係包含下述式(1)表示之化合物,[式(1)中,表示單鍵或雙鍵, X1
表示-N(R1
)-或-CH(R1
)-, X2
表示-N(R2
)-或-CH(R2
)-, X3
表示-N=、-CH=、-N(R3
)-或-CH(R3
)-, X4
表示-N=、-CH=、-N(R4
)-或-CH(R4
)-, R1
、R2
、R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可經C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1]。 [2]如[1]之阻劑下層膜形成組成物,其中式(1)之R1
、R2
、R3
或R4
為羥基或可被羥基取代,且可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基。 [3]一種阻劑下層膜形成組成物,其係包含含有1個單位以上之下述式(2)表示之重複單位a、b、c、d、e、f、g、h、i之1個或複數個的化合物, 式(2) [式(2)中,表示單鍵或雙鍵, X1
表示-N(R1
)-、-CH(R1
)-、-N<或-CH<, X2
表示-N(R2
)-、-CH(R2
)-、-N<或-CH<, X3
表示-N=、-CH=、-N(R3
)-、-CH(R3
)-、-N<或 -CH<, X4
表示-N=、-CH=、-N(R4
)-、-CH(R4
)-、-N<或 -CH<, R1
、R2
、R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可被C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1, B1
與B2
為相同或相異,各自表示氫原子、可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基或選自由C6~40之芳基及C6~40之雜環基所組成之群組之來自芳香族化合物之基,B1
與B2
可與此等所鍵結之碳原子一同形成環,前述來自芳香族化合物之基的氫原子,可被C1~20之烷基、苯基、縮合環基、雜環基、羥基、胺基、醚基、烷氧基、氰基、硝基或羧基取代]。 [4]一種阻劑下層膜形成組成物,其係包含含有1個單位以上之下述式(3)表示之重複單位j、k、l、m、r、s、t、u、v、w之1個或複數個的化合物, 式(3) [式(3)中,表示單鍵或雙鍵, X1
表示-N<或-CH<, X2
表示-N<或-CH<, X3
表示-N=、-CH=、-N(R3
)-或-CH(R3
)-, X4
表示-N=、-CH=、-N(R4
)-或-CH(R4
)-, R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可被C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基,可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1, p及q為0~20之整數, p個之伸甲基及q個之伸甲基為2個以上時,可被氧原子或硫原子中斷, B3
表示直接鍵結、或表示可被C1~20之烷基、苯基、縮合環基、雜環基、羥基、胺基、醚基、烷氧基、氰基、硝基或羧基取代之來自C6~40之芳香族化合物之基]。 [5]一種阻劑下層膜形成組成物,其係包含藉由下述式(1)之化合物與1種類以上之醛化合物之反應、下述式(1)之化合物與1種類以上之芳香族化合物之反應、或下述式(1)之化合物與1種類以上之芳香族化合物與1種類以上之醛化合物之反應所得的樹脂,[式(1)中,表示單鍵或雙鍵, X1
表示-N(R1
)-或-CH(R1
)-, X2
表示-N(R2
)-或-CH(R2
)-, X3
表示-N=、-CH=、-N(R3
)-或-CH(R3
)-, X4
表示-N=、-CH=、-N(R4
)-或-CH(R4
)-, R1
、R2
、R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可被C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1]。 [6]如[5]之阻劑下層膜形成組成物,其中式(1)之R1
、R2
、R3
或R4
為羥基或可被羥基取代,且可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基。 [7]如[1]至[6]中任一項之阻劑下層膜形成組成物,其係進一步包含交聯劑。 [8]如[1]至[7]中任一項之阻劑下層膜形成組成物,其係進一步包含酸及/或酸產生劑。 [9]一種阻劑下層膜之製造方法,其係包含將如[1]至[8]中任一項之阻劑下層膜形成組成物塗佈於半導體基板上,進行燒成的步驟。 [10]一種半導體裝置之製造方法,其係包含以下步驟, 在半導體基板上,藉由如[1]至[8]中任一項之阻劑下層膜形成組成物,形成阻劑下層膜的步驟;其上形成阻劑膜的步驟;藉由光或電子束之照射與顯影,形成阻劑圖型的步驟;藉由阻劑圖型蝕刻該下層膜的步驟;及藉由圖型化後之下層膜,對半導體基板進行加工的步驟。 [11]一種半導體裝置之製造方法,其係包含以下步驟, 在半導體基板上,藉由如[1]至[8]中任一項之阻劑下層膜形成組成物,形成阻劑下層膜的步驟;其上形成硬遮罩的步驟;再於其上形成阻劑膜的步驟;藉由光或電子束之照射與顯影,形成阻劑圖型的步驟;藉由阻劑圖型蝕刻硬遮罩的步驟;藉由圖型化後之硬遮罩蝕刻該下層膜的步驟;及藉由圖型化後之阻劑下層膜,對半導體基板進行加工的步驟。 [12]一種阻劑下層膜形成組成物用樹脂之製造方法,其係包含以下步驟, 使下述式(1)之化合物與1種類以上之醛化合物反應的步驟;使下述式(1)之化合物與1種類以上之芳香族化合物反應的步驟;或使下述式(1)之化合物與1種類以上之芳香族化合物與1種類以上之醛化合物之反應的步驟;[式(1)中,表示單鍵或雙鍵, X1
表示-N(R1
)-或-CH(R1
)-, X2
表示-N(R2
)-或-CH(R2
)-, X3
表示-N=、-CH=、-N(R3
)-或-CH(R3
)-, X4
表示-N=、-CH=、-N(R4
)-或-CH(R4
)-, R1
、R2
、R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可被C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1]。 [發明效果]
本發明之阻劑下層膜材料,不僅具有高蝕刻耐性、高耐熱性,且溶解性高,因此旋轉塗佈性優異,可達成更微細之基板加工。 特別是本發明之阻劑下層膜形成組成物,適合於形成至少2層以阻劑膜厚之薄膜化為目的之阻劑下層膜,以該阻劑下層膜作為蝕刻遮罩使用的微影步驟。 [實施發明之形態]
1.阻劑下層膜形成組成物 本發明之阻劑下層膜形成組成物係包含式(1)表示之化合物及/或式(1)表示之化合物所衍生之聚合物,較佳為進一步包含交聯劑、酸及/或酸產生劑、溶劑及其他的成分者。以下依序說明。
1.1.化合物(I)單體 本發明之阻劑下層膜形成組成物,可包含下述式(1)表示之化合物。[式(1)中,表示單鍵或雙鍵, X1
表示-N(R1
)-或-CH(R1
)-, X2
表示-N(R2
)-或-CH(R2
)-, X3
表示-N=、-CH=、-N(R3
)-或-CH(R3
)-, X4
表示-N=、-CH=、-N(R4
)-或-CH(R4
)-, -表示與鄰接之1個元素之鍵結鍵(單鍵),=表示與鄰接之1個元素之鍵結鍵(雙鍵), R1
、R2
、R3
及R4
為氫原子時,上述之N均為二級氮,C均為二級碳,R1
、R2
、R3
及R4
不為氫原子時,為-N=或 -CH=的情形時,上述之N均為三級氮,C均為三級碳, R1
、R2
、R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可經C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1]。
X1
、X2
、X3
、X4
之至少1個為包含氮原子為佳。
X1
較佳為表示-N(R1
)-。X2
較佳為表示 -N(R2
)-。X3
較佳為表示-CH=。X4
較佳為表示-CH=。
R1
、R2
、R3
、R4
、R5
、R6
、R9
及R10
中之C1~6之醯基,可列舉甲醯基、乙醯基、丙醯基、丁醯基、異丁醯基、戊醯基、異戊醯基等。 C1~6之烷氧基,可列舉甲氧基、乙氧基、n-丙氧基、異丙氧基、n-丁氧基、異丁氧基、tert-丁氧基、sec-丁氧基、n-戊氧基、新戊氧基、n-己氧基、異己氧基、3-甲基戊氧基等,較佳為甲氧基或乙氧基。 C1~6之烷氧基羰基,可列舉甲氧基羰基、乙氧基羰基、n-丙氧基羰基、i-丙氧基羰基、n-丁氧基羰基、i-丁氧基羰基、sec-丁氧基羰基、第三丁氧基羰基、n-戊氧基羰基、n-己氧基羰基等,較佳為甲氧基羰基或乙氧基羰基。
「可被胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基」及「C1~10之直鏈、支鏈或環狀之烷基」中之烷基,可列舉甲基、乙基、n-丙基、n-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等之直鏈烷基、異丙基、sec-丁基、tert-丁基、異戊基、新戊基、1-甲基戊基、異己基、1-丙基丁基、2-乙基己基、異壬基等之支鏈狀烷基、環丙基、環丁基、環戊基、環己基、p-tert-丁基環己基、金剛烷基等之環狀烷基等,較佳為甲基、乙基、n-丙基、n-丁基、異丙基、sec-丁基、tert-丁基,更佳為甲基、乙基、異丙基、sec-丁基、tert-丁基。
被氧原子或硫原子中斷之C1~20之烷基,可列舉例如包含結構單位-CH2
-O-、-CH2
-S-者。-O-、-S-在前述烷基中,可為一單位或二單位以上。被-O-、-S-單位中斷之C1~20之烷基之具體例為甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基等,尚有甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基或十八烷基,且各自被甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基等取代者。較佳為甲氧基、乙氧基、甲硫基、乙硫基,更佳為甲氧基、乙氧基。
C6~20之芳基,可列舉苯基、萘基、聯苯基、蒽基(anthracenyl)、菲基(phenanthryl)、芘基等,較佳為苯基、萘基或聯苯基。 C2~10或C2~20之烯基,可列舉乙烯基、丙烯基、丁烯基等,較佳為乙烯基。 C2~10之炔基,可列舉乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基、癸炔基、丁二炔基( butadiynyl)、戊二炔基、己二炔基、庚二炔基、辛二炔基、壬二炔基、癸二炔基等,較佳為乙炔基、丙炔基、丁炔基。
R1
、R2
、R3
及R4
較佳為羥基或經羥基取代,且可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基。較佳為羥基或可被羥基取代之C1~20之直鏈、支鏈或環狀之烷基。
1.2.化合物(II)聚合物 本發明之阻劑下層膜形成組成物,除式(1)表示之化合物外,或取代此化合物,可包含式(1)表示之化合物所衍生的聚合物。
式(1)表示之化合物所衍生之聚合物,可列舉含有1單位以上之下述式(2)表示之重複單位a、b、c、d、e、f、g、h、i之1個或複數個的化合物。 式(2) [式(2)中,表示單鍵或雙鍵, X1
表示-N(R1
)-、-CH(R1
)-、-N<或-CH<, X2
表示-N(R2
)-、-CH(R2
)-、-N<或-CH<, X3
表示-N=、-CH=、-N(R3
)-、-CH(R3
)-、-N<或 -CH<, X4
表示-N=、-CH=、-N(R4
)-、-CH(R4
)-、-N<或 -CH<, -表示與鄰接之1個元素之鍵結鍵(單鍵),=表示與鄰接之1個元素之鍵結鍵(雙鍵),<表示與鄰接之2個元素各自鍵結之2支鍵結鍵(2支單鍵), R1
、R2
、R3
及R4
為氫原子時,上述之N均為二級氮,C均為二級碳,R1
、R2
、R3
及R4
不為氫原子時,為-N=、 -CH=、-N<或-CH<的情形時,上述之N均為三級氮,C均為三級碳, R1
、R2
、R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可被C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1, B1
與B2
為相同或相異,各自表示氫原子、可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基或選自由C6~40之芳基及C6~40之雜環基所組成之群組之來自芳香族化合物之基,B1
與B2
可與此等所鍵結之碳原子一同形成環,前述來自芳香族化合物之基的氫原子,可被C1~20之烷基、苯基、縮合環基、雜環基、羥基、胺基、醚基、烷氧基、氰基、硝基或羧基取代]。
式(2)中之定義中較佳態樣或具體例,如上述。
B1
與B2
之定義中之C6~40之芳基及C6~40之雜環基係指可為(a)來自如苯之單環之基,也可為(b)來自如萘之縮合環之基,也可為(c)來自如呋喃、噻吩、吡啶之雜環之基,也可為(d)如聯苯基,以單鍵鍵結(a)~(c)之芳香族環之基,也可為(e)以-CH-、-(CH2
)n
-(n=1~20)、 -CH=CH-、-CH≡CH-、-N=N-、-NH-、-NHR-、-NHCO-、 -NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-所例示之間隔基(Spacer),連結有(a)~(d)之芳香族環的化合物。
較佳之芳香族環為苯環、噻吩環、呋喃環、吡啶環、嘧啶環、吡嗪環、吡咯環、噁唑環、噻唑環、咪唑環、萘環、蒽環、喹啉環、咔唑環、喹唑啉環、嘌呤環、吲哚嗪環、苯并噻吩環、苯并呋喃環、吲哚環、及吖啶環。
更佳之芳香族環為苯環、噻吩環、呋喃環、吡啶環、嘧啶環、吡咯環、噁唑環、噻唑環、咪唑環、及咔唑環。
以上的芳香族環,可藉由單鍵或間隔基連結。 間隔基之例,可列舉-CH-、-(CH2
)n
-(n=1~20)、 -CH=CH-、-CH≡CH-、-N=N-、-NH-、-NHR-、-NHCO-、 -NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-一種或二種以上的組合。此等的間隔基可連結2個以上。
縮合環基係指來自縮合環化合物之取代基,具體而言,可列舉苯基、萘基、蒽基、菲基、稠四苯基、聯三伸苯基(triphenylenyl)、芘基及基(chrysenyl),此等之中,較佳為苯基、萘基、蒽基及芘基。
雜環基係指來自雜環式化合物之取代基,具體而言,可列舉噻吩基、呋喃基、吡啶基、嘧啶基、吡嗪基、吡咯基、噁唑基、噻唑基、咪唑基、喹啉基、咔唑基、喹唑啉基、嘌呤基、吲哚嗪基、苯并噻吩基、苯并呋喃基、吲哚基、吖啶基、異吲哚基、苯并咪唑基、異喹啉基、喹喔啉基、噌啉基、蝶啶基、色原烯基(chromene)(苯并吡喃基)、異色原烯基(苯并吡喃基)、呫噸基、噻唑基、吡唑基、咪唑啉基、吖嗪基,此等之中,較佳為噻吩基、呋喃基、吡啶基、嘧啶基、吡嗪基、吡咯基、噁唑基、噻唑基、咪唑基、喹啉基、咔唑基、喹唑啉基、嘌呤基、吲哚嗪基、苯并噻吩基、苯并呋喃基、吲哚基及吖啶基,最佳為噻吩基、呋喃基、吡啶基、嘧啶基、吡咯基、噁唑基、噻唑基、咪唑基及咔唑基。
式(1)表示之化合物所衍生之聚合物,可列舉含有1單位以上之下述式(3)表示之重複單位j、k、l、m、r、s、t、u、v、w之1個或複數個的化合物。 式(3) [式(3)中,表示單鍵或雙鍵, X1
表示-N<或-CH<, X2
表示-N<或-CH<, X3
表示-N=、-CH=、-N(R3
)-或-CH(R3
)-, X4
表示-N=、-CH=、-N(R4
)-或-CH(R4
)-, R3
及R4
為相同或相異,各自表示氫原子、C1~20之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~10之烯基、C2~10之炔基、羧基或氰基,上述烷基及芳基可被C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、胺基、縮水甘油基或羥基取代,且可被氧原子或硫原子中斷, R5
、R6
、R9
及R10
為相同或相異,各自表示氫原子、羥基、C1~6之醯基、C1~6之烷氧基、C1~6之烷氧基羰基、C1~10之直鏈、支鏈或環狀之烷基、C6~20之芳基、C2~20之烯基或C2~10之炔基,上述醯基、烷氧基、烷氧基羰基、烷基、芳基、烯基及炔基,可具有1個或複數個選自由胺基、硝基、氰基、羥基、縮水甘油基及羧基所組成之群組之基, R7
及R8
為相同或相異,各自表示苯環或萘環, n及o為0或1, p及q為0~20之整數, p個之伸甲基及q個之伸甲基為2個以上時,可被氧原子或硫原子中斷, B3
表示直接鍵結、或表示可被C1~20之烷基、苯基、縮合環基、雜環基、羥基、胺基、醚基、烷氧基、氰基、硝基或羧基取代之來自C6~40之芳香族化合物之基]。
式(3)中之定義中較佳態樣或具體例,如上述。
1.3.聚合物之製造方法 本發明之阻劑下層膜形成組成物用樹脂,可藉由包含以下步驟的方法製造, 前述方法包含使上述式(1)之化合物與1種類以上之醛化合物反應的步驟;使上述式(1)之化合物與1種類以上之芳香族化合物反應的步驟;或使上述式(1)之化合物與1種類以上之芳香族化合物與1種類以上之醛化合物之反應的步驟。
醛化合物,可列舉甲醛、聚甲醛、乙醛、三聚甲醛、丙醛、丁醛、三甲基乙醛、丙烯醛、巴豆醛、環己烷醛、糠醛、呋喃基丙烯醛、苯甲醛、對苯二醛、苯基乙醛、α-苯基丙醛、β-苯基丙醛、o-羥基苯甲醛、m-羥基苯甲醛、p-羥基苯甲醛、o-甲基苯甲醛、m-甲基苯甲醛、p-甲基苯甲醛、o-氯苯甲醛、m-氯苯甲醛、p-氯苯甲醛、桂皮醛等。此等之醛化合物,可單獨使用或組合2種類以上使用,較佳為以3種以下,又更佳為以2種以下之組合使用。
芳香族化合物,較佳為衍生二價基 -C(B1
)(B2
)-、-B3
-之C6~40之芳香族化合物,且構成上述式(2)或(3)之聚合物用的一成分。此芳香族化合物,可為(a)如苯之單環化合物,也可為(b)如萘之縮合環化合物,也可為(c)如呋喃、噻吩、吡啶之雜環化合物,也可為(d)如聯苯,以單鍵鍵結(a)~(c)之芳香族環的化合物,也可為(e)以-CH-、-(CH2
)n
-(n=1~20)、-CH=CH-、-CH≡CH-、 -N=N-、-NH-、-NHR-、-NHCO-、-NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-所例示之間隔基,連結有(a)~(d)之芳香族環的化合物。
芳香族化合物,可列舉苯、噻吩、呋喃、吡啶、嘧啶、吡嗪、吡咯、噁唑、噻唑、咪唑、萘、蒽、喹啉、咔唑、喹唑啉、嘌呤、吲哚嗪、苯并噻吩、苯并呋喃、吲哚、吖啶等。
較佳為芳香族胺或含有酚性羥基的化合物。 芳香族胺,可列舉苯基吲哚、苯基萘基胺等。 含有酚性羥基的化合物,可列舉羥基苯、二羥基苯、三羥基苯、羥基萘、二羥基萘、三羥基萘、三(4-羥基苯基)甲烷、三(4-羥基苯基)乙烷、1,1,2,2-四(4-羥基苯基)乙烷等。
上述C6~40之芳香族化合物的氫原子,可被C1~20之烷基、苯基、縮合環基、雜環基、羥基、胺基、醚基、烷氧基、氰基、硝基或羧基取代。 較佳為上述二價基為C6~40之芳基胺化合物所衍生之二價基。
又,以上的芳香族化合物,可藉由單鍵或間隔基連結。 間隔基之例,可列舉-CH-、-(CH2
)n
-(n=1~20)、 -CH=CH-、-CH≡CH-、-N=N-、-NH-、-NHR-、-NHCO-、 -NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-之一種或二種以上之組合。此等之間隔基也可2個以上連結。
又,上述二價基可為胺基、羥基、或包含其兩者之芳香族化合物所衍生的二價基。此外,上述二價基可為芳基胺化合物、苯酚化合物、或包含其兩者之芳香族化合物所衍生的二價基。更具體而言。上述二價基可為苯胺、二苯基胺、苯基萘基胺、羥基聯苯胺、咔唑、苯酚、N,N’-二苯基乙二胺、N,N’-二苯基-1,4-苯二胺、或多環苯酚(polynuclear phenol)所衍生之二價基。
上述多環苯酚,可列舉二羥基苯、三羥基苯、羥基萘、二羥基萘、三羥基萘、三(4-羥基苯基)甲烷、三(4-羥基苯基)乙烷、2,2’-聯苯二酚、或1,1,2,2-四(4-羥基苯基)乙烷等。
此等之芳香族化合物,可單獨使用或組合2種類以上使用,較佳為以3種以下,又更佳為以2種以下之組合使用。
B1
、B2
、B3
可在上述範圍內任意選擇,但是以選擇提供所得之聚合物,充分地溶解於上述本發明所使用的溶劑中,通過口徑0.1μm之微過濾器之阻劑下層膜形成組成物為佳。
反應所使用之酸觸媒,可使用例如硫酸、磷酸、過氯酸等之礦酸類、p-甲苯磺酸、p-甲苯磺酸一水合物、甲磺酸等之有機磺酸類、甲酸、草酸等之羧酸類。酸觸媒之使用量,可藉由使用之酸類的種類來進行各種選擇。相對於芳香族化合物100質量份,通常為0.001至10000質量份,較佳為0.01至1000質量份,更佳為0.1至100質量份。
上述縮合反應與加成反應,也可在無溶劑下進行,通常使用溶劑進行。溶劑只要是不阻礙反應者時,皆可使用。可列舉例如1,2-二甲氧基乙烷、二乙二醇二甲醚、丙二醇單甲醚、四氫呋喃、二噁烷等之醚類。 反應溫度通常為40℃至200℃。反應時間係因反應溫度而有各種選擇,通常為30分鐘至50小時左右。 如以上所得之聚合物的重量平均分子量Mw,通常為500至2,000,000、或600至100,000、或700至10,000、或800至8,000、或900至6,000。 聚合反應的結果,除了可得到含有上述式(2)或上述式(3)表示之重複單位的聚合物外,也可得到式(1)之化合物、芳香族化合物、醛化合物複雜鍵結的聚合物混合物,故實際上不一定可以其結構直接限定。
1.4.交聯劑 本發明之阻劑下層膜形成組成物可包含交聯劑成分。特別是上述式(1)之化合物為單體時,該交聯劑成分可適合使用。該交聯劑,可列舉三聚氰胺系、取代脲系、或彼等之聚合物系等。較佳為具有至少2個交聯形成取代基的交聯劑,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(benzoguanamine)、丁氧基甲基化苯並胍胺、甲氧基甲基化脲、丁氧基甲基化脲、或甲氧基甲基化硫脲等之化合物。又,此等之化合物的縮合體也可使用。
又,作為上述交聯劑,也可使用耐熱性高的交聯劑。耐熱性高的交聯劑,較佳為使用分子內含有具有芳香族環(例如,苯環、萘環)之交聯形成取代基的化合物。
此化合物,可列舉具有下述式(4)之部分結構的化合物或、具有下述式(5)之重複單位的聚合物或寡聚物。上述R11
、R12
、R13
、及R14
為氫原子或碳數1至10之烷基,此等之烷基可使用上述例示。 n1及n2各自表示0~6之整數,n3及n4各自表示0~4之整數。
上述化合物可以旭有機材工業(股)、本州化學工業(股)之製品取得。例如上述交聯劑之中,式(4-23)的化合物,可以商品名TMOM-BP(本州化學工業(股)製)、式(4-24)之化合物,可以商品名TM-BIP-A(旭有機材工業(股)製)取得。 交聯劑之添加量係因使用的塗佈溶劑、使用的基底基板、要求的溶液黏度、要求的膜形狀等而改變,但是相對於全固體成分,一般為0.001至80質量%,較佳為0.01至50質量%,又更佳為0.05至40質量%。此等交聯劑也有藉由自行縮合產生交聯反應,但是本發明之上述的聚合物中存在著交聯性取代基時,可與彼等之交聯性取代基產生交聯反應。
1.5.酸及酸產生劑 本發明中,可添加作為促進上述交聯反應用觸媒之酸及/或酸產生劑。可調配例如,p-甲苯磺酸、三氟甲磺酸、吡啶鎓p-甲苯磺酸、水楊酸、5-磺基水楊酸、4-苯酚磺酸、樟腦磺酸、4-氯苯磺酸、苯二磺酸、1-萘磺酸、檸檬酸、苯甲酸、羥基苯甲酸、萘羧酸等之酸性化合物、及/或2,4,4,6-四溴環己二烯酮、苯偶因對甲苯磺酸酯、2-硝基苄基對甲苯磺酸酯、吡啶鎓p-羥基苯磺酸鹽、吡啶鎓p-甲苯磺酸鹽、吡啶鎓三氟甲烷磺酸鹽等之吡啶鎓鹽系化合物、其他的有機磺酸烷基酯等之熱酸產生劑。調配量係相對於全固體成分,一般為0.0001至20質量%,較佳為0.0005至10質量%,又更佳為0.01至3質量%。
本發明之阻劑下層膜形成組成物,可含有酸產生劑。 酸產生劑,可列舉熱酸產生劑或光酸產生劑。 光酸產生劑係在阻劑之曝光時產生酸。因此,可調整下層膜之酸性度。此乃是為了將下層膜之酸性度與上層之阻劑之酸性度配合用的一種方法。又,藉由下層膜之酸性度之調整,可調整形成於上層之阻劑的圖型形狀。 本發明之阻劑下層膜形成組成物所包含之光酸產生劑,可列舉鎓鹽化合物、磺醯亞胺化合物、及二磺醯基重偶氮甲烷化合物等。
鎓鹽化合物,可列舉二苯基錪六氟磷酸鹽、二苯基錪三氟甲磺酸鹽、二苯基錪九氟正丁烷磺酸鹽、二苯基錪全氟正辛烷磺酸鹽、二苯基錪樟腦磺酸鹽、雙(4-tert-丁基苯基)錪樟腦磺酸鹽及雙(4-tert-丁基苯基)錪三氟甲磺酸鹽等之錪氯化合物、及三苯基鋶六氟銻酸鹽、三苯基鋶九氟正丁烷磺酸鹽、三苯基鋶樟腦磺酸鹽及三苯基鋶三氟甲磺酸鹽等之鋶鹽化合物等。
磺醯亞胺化合物,可列舉例如N-(三氟甲烷磺醯氧基)丁二醯亞胺、N-(九氟正丁烷磺醯氧基)丁二醯亞胺、N-(樟腦磺醯氧基)丁二醯亞胺及N-(三氟甲烷磺醯氧基)萘醯亞胺等。
二磺醯基重氮甲烷化合物,可列舉例如、雙(三氟甲基磺醯基)重氮甲烷、雙(環己基磺醯基)重氮甲烷、雙(苯基磺醯基)重氮甲烷、雙(p-甲苯磺醯基)重氮甲烷、雙(2,4-二甲基苯磺醯基)重氮甲烷、及甲基磺醯基-p-甲苯磺醯基重氮甲烷等。
光酸產生劑可使用僅一種,或可組合二種以上使用。 使用光酸產生劑時,相對於阻劑下層膜形成組成物之固體成分100質量份,其比率為0.01至5質量份、或0.1至3質量份、或0.5至1質量份。
1.6.溶劑 本發明之阻劑下層膜形成組成物係藉由將下述各種聚合物溶解於特定的溶劑中來調製,可以均勻的溶液狀態使用。
本發明之阻劑下層膜形成組成物的溶劑,只要是可溶解上述聚合物的溶劑時,即無特別限定,皆可使用。特別是本發明之阻劑下層膜形成組成物可以均勻的溶液狀態使用,故考慮其塗佈性能時,建議與微影步驟一般使用之溶劑併用。
這種溶劑,可列舉例如甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、丙二醇、丙二醇單甲醚、丙二醇單***、甲基異丁基甲醇、丙二醇單丁醚、丙二醇單甲醚乙酸酯、丙二醇單***乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單丁醚乙酸酯、甲苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、乙氧基乙酸乙脂、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、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、乙二醇單甲醚、乙二醇單***、乙二醇單丙醚、乙二醇單丁醚、乙二醇單甲醚乙酸酯、乙二醇單***乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇二甲醚、二乙二醇二***、二乙二醇二丙醚、二乙二醇二丁醚丙二醇單甲醚、丙二醇二甲醚、丙二醇二***、丙二醇二丙醚、丙二醇二丁醚、乳酸乙酯、乳酸丙酯、乳酸異丙酯、乳酸丁酯、乳酸異丁酯、甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸異丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊酯、甲酸異戊酯、乙酸甲酯、乙酸乙酯、乙酸戊酯、乙酸異戊酯、乙酸己基、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、丙酸丁酯、丙酸異丁酯、丁酸甲酯、丁酸乙酯、丁酸丙酯、丁酸異丙酯、丁酸丁酯、丁酸異丁酯、羥基乙酸乙酯、2-羥基-2-甲基丙酸乙酯、3-甲氧基-2-甲基丙酸甲酯、2-羥基-3-甲基丁酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙脂、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲氧基丙基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基丙酸酯、3-甲基-3-甲氧基丁基丁酸酯、乙醯乙酸甲酯、甲苯、二甲苯、甲基乙基酮、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、環己酮、N、N-二甲基甲醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、4-甲基-2-戊醇、及γ-丁內酯等。此等之溶劑可單獨使用,或可以二種以上之組合使用。
此等之溶劑之中,較佳為丙二醇單甲醚、丙二醇單甲醚乙酸酯、乳酸乙酯、乳酸丁酯、及環己酮等。特別是以丙二醇單甲醚、丙二醇單甲醚乙酸酯為佳。
較佳為本發明之阻劑下層膜形成組成物係包含作為溶劑之式(6)表示之化合物。(式(6)中之R1
、R2
及R3
各自表示氫原子、可被氧原子、硫原子或醯胺鍵中斷之碳原子數1~20之烷基,彼此可相同相異,可彼此鍵結形成環結構)。 式(6)表示之化合物,只要是可與此化合物為相溶性,可溶解上述聚合物的溶劑時,可與上述溶劑併用。
碳原子數1~20之烷基,可列舉可具有取代基,也可不具有取代之具有直鏈或支鏈的烷基,可列舉例如,甲基、乙基、n-丙基、異丙基、n-丁基、sec-丁基、tert-丁基、n-戊基、異戊基、新戊基、n-己基、異己基、n-庚基、n-辛基、環己基、2-乙基己基、n-壬基、異壬基、p-tert-丁基環己基、n-癸基、n-十二烷基壬基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基及二十烷基等。較佳為碳原子數1~12之烷基,更佳為碳原子數1~8之烷基,又更佳為碳原子數1~4之烷基。
被氧原子、硫原子或醯胺鍵中斷之碳原子數1~20之烷基,可列舉例如,含有結構單位-CH2
-O-、 -CH2
-S-、-CH2
-NHCO-或-CH2
-CONH-者。-O-、-S-、 -NHCO-或-CONH-也可為前述烷基中,一單位或二單位以上。被-O-、-S-、-NHCO-或-CONH-單位中斷之碳原子數1~20之烷基的具體例為甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基胺基、乙基羰基胺基、丙基羰基胺基、丁基羰基胺基、甲基胺基羰基、乙基胺基羰基、丙基胺基羰基、丁基胺基羰基等,及甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基或十八烷基,各自被甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基胺基、乙基羰基胺基、甲基胺基羰基、乙基胺基羰基等取代者。較佳為甲氧基、乙氧基、甲硫基、乙硫基,更佳為甲氧基、乙氧基。
此等之溶劑為比較高沸點,故對阻劑下層膜形成組成物也可賦予高埋入性或高平坦化性。
上述式(6)表示之化合物,僅微量包含於阻劑下層膜形成組成物中,即可發揮效果,故其調配量無特別限制。較佳為式(6)表示之化合物,相對於本發明之阻劑下層膜形成組成物全體的重量,包含5重量%以上。又,較佳為式(6)表示之化合物,相對於本發明之阻劑下層膜形成組成物全體之重量,包含30重量%以下。
1.7.界面活性劑 本發明之阻劑下層膜材料中,為了不會發生針孔或條紋等,進一步提高對表面不均之塗佈性,可調配界面活性劑。界面活性劑,可列舉例如聚氧乙烯月桂醚、聚氧乙烯硬脂醚、聚氧乙烯十六醚、聚氧乙烯油醚等之聚氧化乙烯烷醚類、聚氧乙烯辛基酚醚、聚氧乙烯壬基酚醚等之聚氧乙烯烷基烯丙醚類、聚氧乙烯・聚氧丙烯嵌段共聚物類、山梨糖醇酐單月桂酸酯、山梨糖醇酐單棕櫚酸酯、山梨糖醇酐單硬脂酸酯、山梨糖醇酐單油酸酯、山梨糖醇酐三油酸酯、山梨糖醇酐三硬脂酸酯等之山梨糖醇酐脂肪酸酯類、聚氧乙烯山梨糖醇酐單月桂酸酯、聚氧乙烯山梨糖醇酐單棕櫚酸酯、聚氧乙烯山梨糖醇酐單硬脂酸酯、聚氧乙烯山梨糖醇酐三油酸酯、聚氧乙烯山梨糖醇酐三硬脂酸酯等之聚氧乙烯山梨糖醇酐脂肪酸酯類等之非離子系界面活性劑、EFTOPEF301、EF303、EF352((股)TOHKEM PRODUCTS製、商品名)、MegafacF171、F173、R-40、R-40N、R-40LM(DIC(株)製、商品名)、FluoradFC430、FC431(住友3M(股)製、商品名)、AsahiguardAG710、SurflonS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(股)製、商品名)等之氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業(股)製)等。此等之界面活性劑之調配量係相對於阻劑下層膜材料之全固體成分,通常為2.0質量%以下,較佳為1.0質量%以下。此等之界面活性劑可單獨使用,也可以二種以上之組合使用。使用界面活性劑時,相對於阻劑下層膜形成組成物之固體成分100質量份,其比率為0.0001至5質量份、或0.001至1質量份、或0.01至0.5質量份。
1.8.其他之成分 本發明之微影用阻劑下層膜材料中,可添加吸光劑、流變調整劑、接著補助劑等。流變調整劑可有效提高下層膜形成組成物之流動性。接著補助劑可有效提高半導體基板或阻劑與下層膜之密著性。
作為吸光劑,可使用例如「工業用色素之技術與市場」(CMC出版)或「染料便覽」(有機合成化學協會編)所記載之市售的吸光劑,例如C.I.Disperse Yellow 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.D isperse 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 Violet 43;C.I.Disperse Blue 96;C.I.Fluorescent Brightening Agent 112,135及163;C.I.Solvent Orange2及45;C.I.Solvent Red 1,3,8,23,24,25,27及49;C.I.Pigment Green 10;C.I.Pigment Brown 2等。上述吸光劑,相對於微影用阻劑下層膜材料之全固體成分,通常以10質量%以下,較佳為以5質量%以下之比率調配。
流變調整劑主要是提高阻劑下層膜形成組成物之流動性,特別是在烘烤步驟中,以提高阻劑下層膜之膜厚均勻性,或提高對孔內部之阻劑下層膜形成組成物之填充性為目的而添加。具體例,可列舉鄰苯二甲酸二甲酯、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之鄰苯二甲酸衍生物、己二酸二正丁酯、二異丁基己二酸酯、己二酸二異辛酯、己二酸辛基癸酯等之己二酸衍生物、二正丁基馬來酸酯、二乙基馬來酸酯、二壬基馬來酸酯等之馬來酸衍生物、油酸甲酯、油酸丁酯、四氫糠基油酸酯(tetrahydrofurfuryl oleate)等之油酸衍生物、或正丁基硬脂酸酯、甘油基硬脂酸酯等之硬脂酸衍生物。此等之流變調整劑,相對於微影用阻劑下層膜材料之全固體成分,通常以未達30質量%之比率調配。
接著補助劑主要提高基板或阻劑與阻劑下層膜形成組成物之密著性,特別是顯影時避免阻劑剝離為目的而添加。具體例,可列舉三甲基氯矽烷、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之氯矽烷類、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之烷氧基矽烷類、六甲基二矽氮烷、N,N’-雙(三甲基矽烷基)脲、二甲基三甲基矽烷基胺、三甲基矽烷基咪唑等之矽氮烷類、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-環氧丙氧基丙基三甲氧基矽烷等之矽烷類、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、硫脲嘧啶、巰基咪唑、巰基嘧啶等之雜環式化合物或、1,1-二甲基脲、1,3-二甲基脲等之脲、或硫脲化合物。此等之接著補助劑,相對於微影用阻劑下層膜材料之全固體成分,通常以未達5質量%,較佳為以未達2質量%之比率調配。
1.9.阻劑下層膜形成組成物 本發明之阻劑下層膜形成組成物之固體成分,通常為0.1至70質量%,較佳為0.1至60質量%。固體成分為自阻劑下層膜形成組成物除去溶劑後之全成分的含有比率。固體成分中之聚合物的比率為1至100質量%、1至99.9質量%、50至99.9質量%、50至95質量%、50至90質量%的順序為佳。
評價阻劑下層膜形成組成物為均勻的溶液狀態與否之尺度之一為觀察特定之微過濾器的通過性,但是本發明之阻劑下層膜形成組成物係通過口徑0.1μm的微過濾器,呈現均勻的溶液狀態。
上述微過濾器材質,可列舉PTFE(聚四氟乙烯)、PFA(四氟乙烯・全氟烷基乙烯醚共聚物)等之氟系樹脂、PE(聚乙烯)、UPE(超高分子量聚乙烯)、PP(聚丙烯)、PSF(聚碸)、PES(聚醚碸)、尼龍,但是以PTFE(聚四氟乙烯)製為佳。
2.阻劑下層膜及半導體裝置之製造方法 以下說明使用本發明之阻劑下層膜形成組成物之阻劑下層膜及半導體裝置之製造方法。
本發明之阻劑下層膜可藉由將上述阻劑下層膜形成組成物塗佈於半導體基板上,進行燒成來製造。 半導體裝置之製造所使用的基板(例如,矽晶圓基板、矽/二氧化矽被覆基板、氮化矽基板、玻璃基板、ITO基板、聚醯亞胺基板、及低介電常數材料(low-k材料)被覆基板等)之上,藉由旋轉塗佈機、塗佈器等之適當的塗佈方法,塗佈本發明之阻劑下層膜形成組成物後,以燒成形成阻劑下層膜。燒成之條件係自燒成溫度80℃至250℃、燒成時間0.3至60分鐘之中適宜選擇。較佳為燒成溫度150℃至250℃、燒成時間0.5至2分鐘。在此,形成之下層膜之膜厚,例如為10至1000nm,或20至500nm,或30至300nm,或50至300nm,或50至200nm。
又,在本發明之有機阻劑下層膜上,也可形成無機阻劑下層膜(硬遮罩)。例如,除了以旋轉塗佈形成WO2009/104552A1所記載之含有矽之阻劑下層膜(無機阻劑下層膜)形成組成物的方法外,可以CVD法等形成Si系之無機材料膜。
又,將本發明之阻劑下層膜形成組成物塗佈於具有段差之部分與不具有段差之部分的半導體基板(所謂的段差基板)上,藉由燒成可形成該具有段差之部分與不具有段差之部分之段差為3~50nm之範圍內的阻劑下層膜。
其次,在該阻劑下層膜之上形成例如光阻的層。光阻層之形成可藉由公知的方法,亦即,將光阻組成物溶液塗佈於下層膜上進行燒成來進行。光阻之膜厚,例如為50至10000nm,或100至2000nm,或200至1000nm。
形成於阻劑下層膜上之光阻,只要是對曝光所使用之光感光者時,即無特別限定。可使用負型光阻及正型光阻之任一。例如有由酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所成之正型光阻,由藉由酸分解提高鹼溶解速度之基的黏結劑與光酸產生劑所成之化學增強型光阻,由藉由酸分解提高光阻之鹼溶解速度之低分子化合物與鹼可溶性黏結劑與光酸產生劑所成之化學增強型光阻、及由具有藉由酸分解提高鹼溶解速度之基的黏結劑與藉由酸分解提高光阻之鹼溶解速度之低分子化合物與光酸產生劑所成之化學增強型光阻等。可列舉例如,Chypre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SEPR430等。又,可列舉例如Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)、或Proc.SPIE,Vol.3999,365-374(2000)所記載之含氟原子聚合物系光阻。
其次,通過特定之遮罩進行曝光。曝光可使用近紫外線、遠紫外線、或極紫外線(例如、EUV(波長13.5nm))等。具體而言,可使用KrF準分子雷射(波長248nm)、ArF準分子雷射(波長193nm)及F2
準分子雷射(波長157nm)等。此等之中,較佳為ArF準分子雷射(波長193nm)及EUV(波長13.5nm)。曝光後,必要時,也可進行曝光後加熱(post exposure bake)。曝光後加熱係適宜選自由加熱溫度70℃至150℃、加熱時間0.3至10分鐘的條件下進行。
又,本發明中,作為阻劑可取代光阻而使用電子束微影用阻劑。電子束阻劑,可使用負型、正型之任一者。例如有由酸產生劑與具有藉由酸分解改變鹼溶解速度之基的黏結劑所成之化學增強型阻劑、由鹼可溶性黏結劑與酸產生劑與藉由酸分解改變阻劑之鹼溶解速度的低分子化合物所成的化學增強型阻劑、由酸產生劑與具有藉由酸分解改變鹼溶解速度之基的黏結劑與藉由酸分解改變阻劑之鹼溶解速度之低分子化合物所成的化學增強型阻劑、由具有藉由電子束分解改變鹼溶解速度之基之黏結劑所成的非化學增強型阻劑、具有被電子束切斷,改變鹼溶解速度之部位的黏結劑所成的非化學增強型阻劑等。使用此等之電子束阻劑時,與照射源作為電子束,使用光阻的情形同樣,可形成阻劑圖型。
接著,以顯影液進行顯影。藉此,例如使用正型光阻時,曝光後之部分的光阻被除去,形成光阻圖型。 作為顯影液,可列舉例如氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物之水溶液、氫氧化四甲銨、氫氧化四乙銨、膽鹼等之氫氧化四級銨之水溶液、乙醇胺、丙基胺、乙二胺等之胺水溶液等之鹼性水溶液。此外,也可在此等之顯影液中添加界面活性劑等。顯影之條件可適宜選自溫度5至50℃、時間10至600秒。
又,以如此形成之光阻(上層)的圖型作為保護膜,除去無機下層膜(中間層),其次,以圖型化後之光阻及由無機下層膜(中間層)所成之膜作為保護膜,除去有機下層膜(下層)。最後,以圖型化後之無機下層膜(中間層)及有機下層膜(下層)作為保護膜,進行半導體基板加工。
首先,藉由乾蝕刻除去光阻被除去之部分的無機下層膜(中間層),使半導體基板露出。無機下層膜之乾蝕刻,可使用四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷、一氧化碳、氬、氧、氮、六氟化硫、二氟甲烷、三氟化氮及三氟化氯、氯、三氯硼烷及二氯硼烷等之氣體。無機下層膜之乾蝕刻以使用鹵素系氣體為佳,更佳為使用氟系氣體。氟系氣體,可列舉例如四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷、及二氟甲烷(CH2
F2
)等。
然後,以由圖型化後之光阻及無機下層膜所成之膜作為保護膜,除去有機下層膜。有機下層膜(下層)係藉由以氧系氣體之乾蝕刻來進行為佳。因含有許多矽原子之無機下層膜,藉由氧系氣體之乾蝕刻不易被除去的緣故。
最後,進行半導體基板加工。半導體基板之加工係藉由以氟系氣體之乾蝕刻來進行為佳。 氟系氣體,可列舉例如四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷、及二氟甲烷(CH2
F2
)等。
又,阻劑下層膜之上層,在光阻之形成前,可形成有機系的抗反射膜。該使用的抗反射膜組成物,無特別限定,可限制任意選擇使用目前為止在微影步驟慣用者,又,慣用的方法,例如可藉由旋轉塗佈機、塗佈機之塗佈及燒成,形成抗反射膜。
本發明中,可在基板上形成有機下層膜後,其上形成無機下層膜,再於其上被覆光阻。藉此,光阻之圖型寬度變窄,為了防止圖型倒塌,即使薄薄被覆光阻時,也可藉由選擇適當的蝕刻氣體,進行基板加工。例如,以對於光阻為十分快速蝕刻速度之氟系氣體作為蝕刻氣體,可對阻劑下層膜加工,又,以對無機下層膜為十分快速蝕刻速度之氟系氣體作為蝕刻氣體,可對基板加工,此外,以對有機下層膜為十分快速蝕刻速度之氧系氣體作為蝕刻氣體,可進行基板加工。
由阻劑下層膜形成組成物所形成之阻劑下層膜,因在微影步驟使用之光的波長,有時對於該光具有吸收的情形。又,這種的情形時,可作為具有防止自基板之反射光之效果的抗反射膜的功能。此外,本發明之阻劑下層膜形成組成物所形成的下層膜,也可作為硬遮罩產生功能者。本發明之下層膜,也可作為防止基板與光阻之相互作用的層、具有防止對光阻所使用之材料或光阻之曝光時所生成之物質對基板之不良作用之功能的層、具有防止加熱燒成時由基板生成之物質對上層光阻擴散之功能的層、及減少因半導體基板介電體層所致之光阻層之毒化(poisoning)效果用的阻隔層等使用。
又,由阻劑下層膜形成組成物所形成的下層膜,可作為使用於雙鑲嵌(Dual Damascene)製程使用之形成有導通孔之基板,可將孔以無間隙填充之埋入材使用。又,也可作為使具有凹凸之半導體基板之表面平坦化用的平坦化材使用。
[實施例]
以下參照實施例等,更詳細說明本發明,但是本發明不限定於下述的態樣者。
在100mL之二口燒瓶中,加入BINFL(旭有機材股份公司製)3.17g、1-芘羧基醛(Aldrich製)3.00g、N-甲基-2-吡咯烷酮(關東化學股份公司製)15.03g、丙二醇單甲醚乙酸酯15.03g、甲磺酸(東京化成工業股份公司製)0.25g。然後,加熱至150℃,迴流攪拌約15小時。反應終了後,使用環己酮25.24g稀釋。將此稀釋溶液滴下至甲醇溶液中,使再沉澱。將所得之沉澱物進行吸引過濾,過濾物以60℃減壓乾燥一晚。然後,得到粉末的樹脂4.85g。所得之聚合物相當於式(2-1)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為1,870。
在100mL之二口燒瓶中,加入BINFL(旭有機材股份公司製)5.45g、9-茀酮(東京化成工業股份公司製)4.00g、N-甲基-2-吡咯烷酮(關東化學股份公司製) 9.76g、丙二醇單甲醚乙酸酯9.76g、甲磺酸(東京化成工業股份公司製)1.07g。然後,加熱至150℃,迴流攪拌約19小時。反應終了後,使用環己酮17.19g稀釋。將此稀釋溶液滴下至甲醇溶液中,使再沉澱。將所得之沉澱物進行吸引過濾,過濾物以60℃減壓乾燥一晚。然後,得到粉末的樹脂8.35g。所得之聚合物相當於式(2-2)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為4,850。
100mL二口燒瓶中加入BINFL(旭有機材股份公司製)7.65g、2-乙基己醛(Hexanal)(東京化成工業股份公司製)4.00g、N-甲基-2-吡咯烷酮(關東化學股份公司製) 9.86g、丙二醇單甲醚乙酸酯9.86g、甲磺酸(東京化成工業股份公司製)1.50g。然後,加熱至150℃,迴流攪拌約19小時。反應終了後,使用環己酮5.96g稀釋。將此稀釋溶液滴下至甲醇溶液中,使再沉澱。將所得之沉澱物之上澄液進行傾析除去後,以60℃減壓乾燥一晚。然後,得到粉末的樹脂10.75g。所得之聚合物相當於式(2-3)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為1,130。
在100mL之二口燒瓶中加入DM-BINFL(旭有機材股份公司製)3.56g、咔唑(東京化成工業股份公司製)1.50g、N-甲基-2-吡咯烷酮(關東化學股份公司製) 4.18g、丙二醇單甲醚乙酸酯4.18g、甲磺酸(東京化成工業股份公司製)0.51g。然後,加熱至150℃,迴流攪拌約15小時。反應終了後,使用環己酮11.32g稀釋。將此稀釋溶液滴下至甲醇溶液中,使再沉澱。將所得之沉澱物進行吸引過濾後,將過濾物以60℃減壓乾燥一晚。然後,得到粉末的樹脂2.36g。所得之聚合物相當於式(3-1)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為1,840。
在100mL之二口燒瓶中加入DM-BINFL(旭有機材股份公司製)4.69g、二苯基胺(東京化成工業股份公司製)4.69g、N-甲基-2-吡咯烷酮(關東化學股份公司製) 5.52g、丙二醇單甲醚乙酸酯5.52g、甲磺酸(東京化成工業股份公司製)0.67g。然後,加熱至150℃,迴流攪拌約19小時。反應終了後,使用環己酮15.03g稀釋。將此稀釋溶液滴下至甲醇溶液中,使再沉澱。將所得之沉澱物進行吸引過濾後,將過濾物以60℃減壓乾燥一晚。然後,得到粉末的樹脂3.38g。所得之聚合物相當於式(3-2)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為2,860。
在100mL之二口燒瓶中,加入DM-BINFL(旭有機材股份公司製)5.18g、1,1,1-三(4-羥基苯基)乙烷(東京化成工業股份公司製)4.00g、N-甲基-2-吡咯烷酮(關東化學股份公司製)7.53g、丙二醇單甲醚乙酸酯7.53g、甲磺酸(東京化成工業股份公司製)0.87g。然後,加熱至150℃,迴流攪拌約19小時。反應終了後,使用環己酮5.47g稀釋。將此稀釋溶液滴下至甲醇溶液中,使再沉澱。將所得之沉澱物進行吸引過濾後,將過濾物以60℃減壓乾燥一晚。然後,得到粉末的樹脂5.18g。所得之聚合物相當於式(3-3)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為1,270。
(比較合成例1)在100mL二口燒瓶中加入9,9-雙(4-羥基)茀(東京化成工業股份公司製)8.00g、1-芘羧基醛(Aldrich製)5.30g、丙二醇單甲醚乙酸酯20.77g、甲磺酸(東京化成工業股份公司製)0.55g。然後,加熱至150℃,迴流攪拌約16.5小時。反應終了後,使用環己酮34.62g稀釋。將此稀釋溶液滴下至甲醇溶液中,使再沉澱。將所得之沉澱物進行吸引過濾後,將過濾物以60℃減壓乾燥一晚。然後,得到粉末的樹脂7.05g。所得之聚合物相當於式(1-1)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為2,260。
在100mL之二口燒瓶中加入9,9-雙(4-羥基)茀(東京化成工業股份公司製)8.00g、9-茀酮(東京化成工業股份公司製)4.11g、丙二醇單甲醚乙酸酯19.49g、甲磺酸(東京化成工業股份公司製)0.88g。然後,加熱至150℃,迴流攪拌約16.5小時。反應終了後,使用環己酮28.09g稀釋。將此稀釋溶液滴下至甲醇/水(80質量%/20質量%)溶液中,使再沉澱。將所得之沉澱物進行吸引過濾後,將過濾物以60℃減壓乾燥一晚。然後,得到粉末的樹脂6.49g。所得之聚合物相當於式(1-2)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為4,600。
在100mL之二口燒瓶中加入9,9-雙(4-羥基)茀(東京化成工業股份公司製)10.00g、2-乙基己醛(東京化成工業股份公司製)3.66g、丙二醇單甲醚乙酸酯22.13g、甲磺酸(東京化成工業股份公司製)1.10g。然後,加熱至150℃,迴流攪拌約16.5小時。反應終了後,使用丙二醇單甲醚乙酸酯8.64g稀釋。將此稀釋溶液滴下至甲醇/水(50質量%/50質量%)溶液中,使再沉澱。將所得之沉澱物之上澄液進行傾析除去後,以60℃減壓乾燥一晚。然後,得到粉末的樹脂14.21g。所得之聚合物相當於式(1-3)。藉由GPC以聚苯乙烯換算測量之重量平均分子量Mw為1,420。
(實施例1) 將合成例1所得之樹脂溶解於環己酮後,經過離子交換,得到樹脂溶液(固體成分為18.45質量%)。在此樹脂溶液5.50g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.20g、丙二醇單甲醚乙酸酯0.714g、環己酮3.75g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例2) 將合成例2所得之樹脂溶解於環己酮後,經過離子交換,得到樹脂溶液(固體成分為18.85質量%。在此樹脂溶液5.00g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.19g、丙二醇單甲醚乙酸酯0.895g、環己酮5.66g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例3) 將合成例3所得之樹脂溶解於丙二醇單甲醚乙酸酯後,經過離子交換,得到樹脂溶液(固體成分為16.50質量%)。在此樹脂溶液6.50g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.11g、丙二醇單甲醚乙酸酯1.23g、丙二醇單甲醚2.90g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例4) 將合成例4所得之樹脂溶解於環己酮後,經過離子交換,得到樹脂溶液(固體成分為16.45質量%)。在此樹脂溶液6.00g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.20g、丙二醇單甲醚乙酸酯0.695g、環己酮3.00g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例5) 將合成例5所得之樹脂溶解於環己酮後,經過離子交換,得到樹脂溶液(固體成分為19.70質量%)。在此樹脂溶液4.80g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.19g、丙二醇單甲醚乙酸酯0.901g、環己酮5.90g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例6) 將合成例6所得之樹脂溶解於丙二醇單甲醚後,經過離子交換,得到樹脂溶液(固體成分為17.40質量%)。在此樹脂溶液5.00g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.09g、丙二醇單甲醚乙酸酯2.91g、丙二醇單甲醚2.88g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例7) 使BINFL(旭有機材股份公司製)溶解於環己酮中,得到含有BINFL之環己酮溶液(固體成分為21.74質量%)。在此溶液1.45g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚0.06g、TMOM-BP(本州化學工業(股)製)0.09g、含有2%K-PURE TAG2689(King Industries公司製三氟甲磺酸系化合物)之丙二醇單甲醚0.47g、環己酮3.89g、丙二醇單甲醚0.03g,經充分攪拌後,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例8) 使DM-BINFL(旭有機材股份公司製)溶解於環己酮中,得到含有DM-BINFL之環己酮溶液(固體成分為18.63質量%)。此溶液1.69g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚0.06g、TMOM-BP(本州化學工業(股)製) 0.09g、含有2%K-PURE TAG2689(King Industries公司製三氟甲磺酸系化合物)之丙二醇單甲醚0.47g、環己酮3.64g、丙二醇單甲醚0.03g,充分攪拌後,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(實施例9) 將合成例1所得之樹脂溶解於環己酮後,經過離子交換,得到樹脂溶液(固體成分為18.45質量%)。在此樹脂溶液3.00g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚0.07g、TMOM-BP(本州化學工業(股)製) 0.21g、含有2%K-PURE TAG2689(King Industries公司製三氟甲磺酸系化合物)之丙二醇單甲醚1.06g、環己酮6.91g、丙二醇單甲醚0.51g,充分攪拌後,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(比較例1) 將比較合成例1所得之樹脂溶解於環己酮後,經過離子交換,得到樹脂溶液(固體成分為22.65質量%)。在此樹脂溶液5.50g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.11g、丙二醇單甲醚乙酸酯1.19g、環己酮7.87g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(比較例2) 將比較合成例2所得之樹脂溶解於丙二醇單甲醚乙酸酯後,經過離子交換,得到樹脂溶液(固體成分為21.95質量%)。此樹脂溶液6.50g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.14g、丙二醇單甲醚乙酸酯3.78g、丙二醇單甲醚3.86g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(比較例3) 將比較合成例3所得之樹脂溶解於丙二醇單甲醚乙酸酯後,經過離子交換,得到樹脂溶液(固體成分為20.67質量%)。在此樹脂溶液7.00g中加入含有1%界面活性劑(DIC(股)製、Megafac R-40)之丙二醇單甲醚乙酸酯0.14g、丙二醇單甲醚乙酸酯3.43g、丙二醇單甲醚3.91g,使用口徑0.1μm之聚四氟乙烯製微過濾器過濾,調製阻劑下層膜形成組成物溶液。
(對阻劑溶劑之溶出試驗) 將比較例1-3及實施例1-9調製之阻劑下層膜形成組成物的溶液分別使用旋轉塗佈機,塗佈於矽晶圓上,在加熱板上以400℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm)。又,比較例3從耐熱性的觀點,膜厚之維持困難,故以350℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm),而實施例7-9係以240℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm)。將此等阻劑下層膜浸漬於阻劑所使用之溶劑的乳酸乙酯、丙二醇單甲醚、丙二醇單甲醚乙酸酯、及環己酮。此等阻劑下層膜不溶於此等溶劑中。
(光學常數測量) 將比較例1-3及實施例1-9調製之阻劑下層膜形成組成物的溶液分別使用旋轉塗佈機,塗佈於矽晶圓上。在加熱板上以400℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.05μm)。又,比較例3從耐熱性的觀點,膜厚之維持困難,故以350℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm),而實施例7-9係以240℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm)。將此等之阻劑下層膜使用分光橢圓測厚儀,測量波長193nm、248nm下之折射率(n值)及光學吸光係數(k值、也稱為減衰係數)。結果如表1所示。
(乾蝕刻速度之測量) 乾蝕刻速度之測量用的蝕刻機(etcher)及蝕刻氣體為使用以下者。 RIE-10NR(Samco製):CF4
將比較例1-3及實施例1-9調製之阻劑下層膜形成組成物的溶液分別使用旋轉塗佈機,塗佈於矽晶圓上。在加熱板上以400℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm)。又,比較例3從耐熱性的觀點,膜厚之維持困難,故以350℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm),而實施例7-9係以240℃進行90秒鐘燒成,形成阻劑下層膜(膜厚0.20μm)。使用作為蝕刻氣體之CF4
氣體,測量乾蝕刻速度,將比較例1-3及實施例1-9之阻劑下層膜之乾蝕刻速度進行比較。結果如表3所示。乾蝕刻速度比為(阻劑下層膜)/(KrF光阻)之乾蝕刻速度比。
(阻劑下層膜之耐熱性試驗) 將比較例1-3及實施例1-6調製之阻劑下層膜形成組成物的溶液分別使用旋轉塗佈機,塗佈於矽晶圓上,在加熱板上以400℃進行1分30秒或以350℃進行1分30秒燒成,形成阻劑下層膜(膜厚0.20μm)。將所得之膜由室溫(約20℃),以每一分鐘10℃的比率昇溫加熱,在大氣中進行熱重量分析,追蹤重量減少之經過時間變化。結果如表3所示。
依據本發明時,可提供具有良好的塗佈性,且賦予高蝕刻耐性、高耐熱性等優異之阻劑下層膜的阻劑下層膜形成組成物。
Claims (12)
- 一種阻劑下層膜形成組成物,其係包含下述式(1)表示之化合物,
- 如請求項1之阻劑下層膜形成組成物,其中式(1)之R1、R2、R3或R4為羥基或可被羥基取代,且可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基。
- 一種阻劑下層膜形成組成物,其係包含含有1個單位以上之下述式(2)表示之重複單位a、b、c、d、e、f、g、h、i之1個或複數個的化合物,
- 一種阻劑下層膜形成組成物,其係包含含有1個單位以上之下述式(3)表示之重複單位j、k、l、m、r、s、t、u、v、w之1個或複數個的化合物,
- 一種阻劑下層膜形成組成物,其係包含藉由下述式(1)之化合物與1種類以上之醛化合物之反應、下述式(1)之化合物與1種類以上之芳香族化合物之反應、或下述式(1) 之化合物與1種類以上之芳香族化合物與1種類以上之醛化合物之反應所得的樹脂,
- 如請求項5之阻劑下層膜形成組成物,其中式(1)之R1、R2、R3或R4為羥基或可被羥基取代,且可被氧原子或硫原子中斷之C1~20之直鏈、支鏈或環狀之烷基。
- 如請求項1至請求項6中任一項之阻劑下層膜形成組成物,其係進一步包含交聯劑。
- 如請求項1至請求項6中任一項之阻劑下層膜形成組成物,其係進一步包含酸及/或酸產生劑。
- 一種阻劑下層膜之製造方法,其係包含將如請求項1至請求項8中任一項之阻劑下層膜形成組成物塗佈於半導體基板上,進行燒成的步驟。
- 一種半導體裝置之製造方法,其係包含以下步驟, 在半導體基板上,藉由如請求項1至請求項8中任一項之阻劑下層膜形成組成物,形成阻劑下層膜的步驟;其上形成阻劑膜的步驟;藉由光或電子束之照射與顯影,形成阻劑圖型的步驟;藉由阻劑圖型蝕刻該下層膜的步驟;及藉由圖型化後之下層膜,對半導體基板進行加工的步驟。
- 一種半導體裝置之製造方法,其係包含以下步驟,在半導體基板上,藉由如請求項1至請求項8中任一項之阻劑下層膜形成組成物,形成阻劑下層膜的步驟;其上形成硬遮罩的步驟;再於其上形成阻劑膜的步驟;藉由光或電子束之照射與顯影,形成阻劑圖型的步驟;藉由阻劑圖型蝕刻硬遮罩的步驟;藉由圖型化後之硬遮罩蝕刻該下層膜的步驟;及藉由圖型化後之阻劑下層膜,對半導體基板進行加工的步驟。
- 一種阻劑下層膜形成組成物用樹脂之製造方法,其係包含以下步驟,使下述式(1)之化合物與1種類以上之醛化合物反應的步驟;使下述式(1)之化合物與1種類以上之芳香族化合物反應的步驟;或使下述式(1)之化合物與1種類以上之芳香族化合物與1種類以上之醛化合物之反應的步驟;
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