TWI823950B - 包含與縮水甘油酯化合物之反應產物的阻劑下層膜形成組成物 - Google Patents
包含與縮水甘油酯化合物之反應產物的阻劑下層膜形成組成物 Download PDFInfo
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- TWI823950B TWI823950B TW108121194A TW108121194A TWI823950B TW I823950 B TWI823950 B TW I823950B TW 108121194 A TW108121194 A TW 108121194A TW 108121194 A TW108121194 A TW 108121194A TW I823950 B TWI823950 B TW I823950B
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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
- GPHXJBZAVNFMKX-UHFFFAOYSA-M triethyl(phenyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)C1=CC=CC=C1 GPHXJBZAVNFMKX-UHFFFAOYSA-M 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
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 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
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- 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
- G03F7/094—Multilayer resist systems, e.g. planarising 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
- 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
- C08G59/26—Di-epoxy compounds heterocyclic
-
- 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
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- 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
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Abstract
本發明係提供特別是具有高乾蝕刻速度之阻劑下層膜、該阻劑下層膜形成組成物、阻劑圖型之形成方法及半導體裝置之製造方法。
一種阻劑下層膜形成組成物,其係包含藉由以下述式(1)表示之化合物、與環氧加成物(adduct)形成化合物之反應所得之環氧加成產物及溶劑。
Description
本發明係有關特別是具有高乾蝕刻速度之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。
將阻劑膜進行曝光時,反射波會對該阻劑膜有不良影響的情形。為了抑制此情形之目的所形成之阻劑下層膜,也稱為抗反射膜。
阻劑下層膜係藉由塗佈溶液狀之阻劑下層膜形成用組成物,使硬化可容易成膜而求得。因此,該組成物必須包含藉由加熱等容易硬化,同時對於特定溶劑之溶解性高的化合物(聚合物)。
於阻劑下層膜上所形成之阻劑圖型,較佳為對基板垂直方向之剖面形狀為矩形狀(並無所謂之底切(undercut)、摺邊(hemming)等之垂直的邊緣形狀)。例如,阻劑圖型成為底切形狀或摺邊形狀時,在阻劑圖型之倒塌、微影步驟時,會發生無法將被加工物(基板、絕緣膜等)加工成所期望的形狀或尺寸的問題。
又,阻劑下層膜被要求乾蝕刻速度大於上層之阻劑膜,亦即,乾蝕刻速度之選擇比較大。
專利文獻1揭示使用在主鏈上具有二硫醚鍵結之聚合物的阻劑下層膜形成組成物。專利文獻2揭示具有縮水甘油酯基之環氧化合物。專利文獻3揭示抗反射膜形成組成物,其係包含具有作為氮原子上之取代基之羥基烷基結構的三嗪三酮化合物、寡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]
半導體元件之製造時,仍然要求具有高乾蝕刻速度的阻劑下層膜。為了形成具有高乾蝕刻速度之阻劑下層膜時,使用在組成物之聚合物中包含雜原子者已為人知。
本案發明人精心檢討的結果,為了使阻劑下層膜中,以更高濃度含有雜原子時,而檢討各種化合物及其反應產物(寡聚物及聚合物)的結果,發現使具有縮水甘油酯基之含氮雜環化合物(異三聚氰酸等)與羧酸等之環氧加成物形成化合物反應的環氧加成產物使用於阻劑下層膜形成組成物時,可達成比以往技術更高蝕刻速率化。
本發明有鑑於這種課題解決,本發明之目的為提供具有特別是高乾蝕刻速度之阻劑下層膜形成組成物而完成者。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]
本發明包含以下者。
[1]一種下述式(1)表示之化合物。
(式(1)中,X為下述式(2)、式(3)或式(4)表示之2價之有機基,n1
、n2
各自獨立表示1至10之整數。)
(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之碳原子數1至10之烷基、可被氧原子或硫原子中斷之碳原子數2至10之烯基、可被氧原子或硫原子中斷之碳原子數2至10之炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6之烷基、鹵素原子、原子數1至10之烷氧基、硝基、氰基及碳原子數1至6之烷硫基所成群之至少1個之1價的官能基取代。
R3
表示氫原子、可被氧原子或硫原子中斷之碳原子數1至10之烷基、可被氧原子或硫原子中斷之碳原子數3至10之烯基、可被氧原子或硫原子中斷之碳原子數3至10之炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6之烷基、鹵素原子、碳原子數1至10之烷氧基、硝基、氰基、碳原子數1至6之烷硫基及下述式(5)表示之有機基所成群之至少1個之1價的官能基取代。)
(式(5)中,n3表示1至10之整數)。
[2]如[1]之化合物,其中前述式(1)中,X為式(4)表示。
[3]如[2]之化合物,其中前述式(1)中,n1及n2為1,R3
為可被氧原子中斷之碳原子數1至5之烷基或以式(5)表示。
[4]一種阻劑下層膜形成組成物,其係包含藉由如[1]至[3]中任一項之化合物、與環氧加成物形成化合物之反應所得之環氧加成產物及溶劑。
[5]如[4]之阻劑下層膜形成組成物,其中前述環氧加成物形成化合物為選自由含羧酸之化合物、含羧酸酐之化合物、含羥基之化合物、含硫醇基之化合物、含胺基之化合物及含醯亞胺基之化合物所成群之至少1種的化合物。
[6]如[4]或[5]之阻劑下層膜形成組成物,其中前述環氧加成物形成化合物為含羧酸之化合物或含硫醇基之化合物。
[7]如[6]之阻劑下層膜形成組成物,其中前述含羧酸之化合物為含有至少1個以上之硫原子的二羧酸。
[8]如[7]之阻劑下層膜形成組成物,其中前述有至少1個以上之硫原子的二羧酸為脂肪族二羧酸。
[9]如[4]至[8]中任一項之阻劑下層膜形成組成物,其係進一步含有交聯觸媒。
[10]如[4]至[9]中任一項之阻劑下層膜形成組成物,其係進一步含有交聯劑。
[11]如[4]至[10]中任一項之阻劑下層膜形成組成物,其係進一步含有界面活性劑。
[12]一種阻劑下層膜,其係由如[4]至[11]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。
[13]一種經圖型化之基板的製造方法,其係包含下步驟:
在半導體基板上塗佈如[4]至[11]中任一項之阻劑下層膜形成組成物,經烘烤形成阻劑下層膜的步驟,
在前述阻劑下層膜上塗佈阻劑,經烘烤形成阻劑膜的步驟,
將以前述阻劑下層膜與前述阻劑被覆之半導體基板進行曝光的步驟,及
將曝光後之前述阻劑膜顯影,進行圖型化的步驟。
[14]一種半導體裝置之製造方法,其係包含下步驟:
在半導體基板上形成如[4]至[11]中任一項之阻劑下層膜形成組成物所成之阻劑下層膜的步驟,
在前述阻劑下層膜上形成阻劑膜的步驟,
藉由對阻劑膜照射光或電子束與其後之顯影,形成阻劑圖型的步驟,
經由所形成之前述阻劑圖型,藉由蝕刻前述阻劑下層膜,形成經圖型化的阻劑下層膜的步驟,及
藉由經圖型化之前述阻劑下層膜,將半導體基板進行加工的步驟。
[發明效果]
本發明之阻劑下層膜形成組成物,具有高乾蝕刻速度,可解決因阻劑膜厚之薄膜化所致之各種的問題,達成更微細之半導體基板之微細加工。
[實施發明之形態]
<化合物>
本案使用的化合物,較佳為形成在阻劑下層膜形成組成物中所含有之環氧加成產物用的環氧化合物為下述式(1)表示之化合物。
(式(1)中,X為下述式(2)、式(3)或式(4)表示之2價之有機基,n1
、n2
各自獨立表示1至10之整數。)
(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之碳原子數1至10之烷基、可被氧原子或硫原子中斷之碳原子數2至10之烯基、可被氧原子或硫原子中斷之碳原子數2至10之炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6之烷基、鹵素原子、碳原子數1至6之烷氧基、硝基、氰基及碳原子數1至6之烷硫基所成群之至少1個之1價的官能基取代。
R3
表示氫原子、可被氧原子或硫原子中斷之碳原子數1至10之烷基、可被氧原子或硫原子中斷之碳原子數2至10之烯基、可被氧原子或硫原子中斷之碳原子數2至10之炔基、苄基或苯基,前述苯基可被選自由碳原子數1至6之烷基、鹵素原子、碳原子數1至6之烷氧基、硝基、氰基、碳原子數1至6之烷硫基及下述式(5)表示之有機基所成群之至少1個之1價的官能基取代。)
(式(5)中,n3表示1至10之整數)。
碳原子數1至10之烷基,可列舉甲基、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。
碳原子數2至10之烯基,可列舉乙烯基、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-伸甲基-環戊基、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-伸甲基-環戊基、1-環己烯基、2-環己烯基及3-環己烯基等。
碳原子數2至10之炔基,可列舉乙炔基、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。
可被氧原子或硫原子中斷係指例如上述烷基、烯基及炔基所包含之碳原子可被氧原子或硫原子取代。例如,烷基中,烯基中及炔基中之某碳原子被氧原子取代時,包含醚鍵,例如烷基中,烯基中及炔基中之某碳原子被硫原子取代時,包含硫醚鍵。
碳原子數1至6之烷基係上述碳原子數1至10之烷基之中,碳原子數為1至6之烷基。
鹵素原子可列舉氟、氯、溴及碘。
碳原子數1至10之烷氧基,可列舉甲氧基、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。
碳原子數1至6之烷硫基,可列舉乙硫基、丁硫基、己硫基等。
前述式(1)中,X以式(4)表示為佳。
前述式(1)中,X以式(4)表示,n1及n2為1,R3
為可被氧原子中斷之碳原子數1至5之烷基較佳。此時,碳原子數1至5之烷基之具體例係上述碳原子數1至10之烷基之中,碳原子數1至5之烷基。
前述式(1)中,X以式(4)表示,n1及n2為1,R3
為甲基、甲氧基甲基或以式(5)表示,n3為1之以下式(A-1)、式(A-7)或式(A-19)表示之化合物較佳。
本案之式(1)表示之化合物,例如可以下述式(A-1)至(A-21)例示,但是不限定於此等。
<環氧加成產物、環氧加成物形成化合物>
本案之環氧加成產物係含羧酸之化合物、含羧酸酐之化合物、含羥基之化合物、含硫醇基之化合物、含胺基之化合物及含醯亞胺基之化合物等之環氧加成物形成化合物以習知的方法加成於上述式(1)表示之環氧化合物所形成。
本案之環氧加成物形成化合物,例如可以下述式(B-1)至(B-53)例示,但是不限定於此等。
此等之環氧加成物形成化合物之中,較佳為含羧酸之化合物(例如上述式(B-1)至(B-25))或含硫醇基之化合物(例如上述式(B-7)、(B-10)、(B-34)至(B-41))。
前述含羧酸之化合物,較佳為包含至少1個以上之硫原子的二羧酸(例如上述式(B-7)、(B-11)~(B-17))。
前述包含至少1個以上之硫原子的二羧酸,較佳為脂肪族二羧酸,特佳為硫代二乙醇酸(Dithioglycolic Acid)(式(B-15))。
上述式(1)表示之化合物與、環氧加成物形成化合物之反應時之莫耳數的比例,例如為1:0.1~10。較佳為1:1~5,又更佳為1:1~3。
本案之環氧加成物之重量平均分子量,例如為1,000~100,000,或1,100~50,000,或1,200~30,000,或1,300~20,000。
[溶劑]
本發明之阻劑下層膜形成組成物,可藉由將上述各成分溶解於有機溶劑來製造,且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,只要可溶解上述化合物、或其反應產物的溶劑時,即無特別限制,皆可使用。特別是本發明之阻劑下層膜形成組成物係以均勻的溶液狀態使用者,故考慮其塗佈性能時,推薦併用在微影步驟通常使用的溶劑。
前述有機溶劑,可列舉例如乙二醇單甲醚、乙二醇單乙醚、甲基溶纖素乙酸酯、乙基溶纖素乙酸酯、二乙二醇單甲醚、二乙二醇單乙醚、丙二醇、丙二醇單甲醚、丙二醇單乙醚、丙二醇單甲醚乙酸酯、丙二醇丙醚乙酸酯、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-羥基異丁酸甲酯、2-羥基異丁酸乙基、乙氧基乙酸乙脂、乙酸2-羥基乙基、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。此等之溶劑,可單獨使用或組合2種以上使用。
此等溶劑之中,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。
[交聯觸媒]
本發明之阻劑下層膜形成組成物,為了促進交聯反應,可含有作為任意成分之交聯觸媒。該交聯觸媒除了酸性化合物、鹼性化合物外,可使用藉由熱產生酸或鹼的化合物。酸性化合物可使用磺酸化合物或羧酸化合物,藉由熱產生酸的化合物,可使用熱酸產生劑。
磺酸化合物或羧酸化合物,可列舉例如p-甲苯磺酸、三氟甲磺酸、吡啶鎓三氟甲烷磺酸鹽、吡啶鎓-p-甲苯磺酸鹽、水楊酸、樟腦磺酸、5-磺水楊酸、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。
熱酸產生劑可列舉例如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公司製)。
此等交聯觸媒,可使用1種或組合2種以上使用。又,鹼性化合物可使用胺化合物或氫氧化銨化合物,藉由熱產生鹼的化合物,可使用脲。
胺化合物可列舉例如三乙醇胺、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、十八烷基二乙醇胺、及二氮雙環辛烷等之三級胺、吡啶及4-二甲基胺基吡啶等之芳香族胺。又,苄基胺及正丁基胺等之一級胺、二乙基胺及二正丁基胺等之二級胺也可列舉作為胺化合物。此等之胺化合物可單獨使用或組合2種以上使用。
氫氧化銨化合物,可列舉例如氫氧化四甲銨、氫氧化四乙銨、氫氧化四丙銨、氫氧化四丁銨、氫氧化苄基三甲基銨、氫氧化苄基三乙基銨、氫氧化十六烷基三甲基銨、氫氧化苯基三甲基銨、氫氧化苯基三乙基銨。
又,藉由熱產生鹼的化合物,例如可使用具有如醯胺基、胺基甲酸酯基或氮丙啶基之熱不安定性基,藉由加熱生成胺的化合物。其他,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、膽鹼氯化物,也為藉由熱產生鹼的化合物。
前述阻劑下層膜形成組成物包含交聯觸媒時,其含量係相對於阻劑下層膜形成組成物之全固體成分,為0.0001~20質量%,較佳為0.01~15質量%,又更佳為0.1~10質量%。
上述之中,酸性化合物及/或藉由熱產生酸的化合物(交聯酸觸媒)為佳。
[交聯劑]
本發明之阻劑下層膜形成組成物可含有交聯劑成分。其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個之交聯形成取代基的交聯劑,例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、或甲氧基甲基化硫脲等之化合物。又,也可使用此等之化合物之縮合體。
又,上述交聯劑可使用耐熱性高的交聯劑。耐熱性高的交聯劑,可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(5-1)之部分結構的化合物或具有下述式(5-2)之重複單位的聚合物或寡聚物。
上述R11
、R12
、R13
、及R14
為氫原子或碳原子數1~10之烷基。m1、m2、m3及m4各自表示0~3之整數。碳原子數1~10之烷基,可列舉甲基、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。
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)之化合物、聚合物、寡聚物如以下所例示。
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(6-22)之化合物可以旭有機材工業(股)、商品名TMOM-BP取得。
交聯劑之添加量係因使用之塗佈溶劑、使用之基底基板、所要求之溶液黏度、所要求之膜形狀等而變動,但是相對於阻劑下層膜形成組成物之全固體成分,為0.001~80重量%,較佳為0.01~50重量%,又更佳為0.1~40重量%。此等交聯劑有藉由自行縮合產生交聯反應,但是本發明之上述聚合物中存在交聯性取代基時,可與彼等之交聯性取代基產生交聯反應。
[界面活性劑]
本發明之阻劑下層膜形成組成物,為了提高對半導體基板之塗佈性時,可含有作為任意成分之界面活性劑。前述界面活性劑,可列舉例如聚氧乙烯月桂醚、聚氧乙烯十八烷基醚、聚氧乙烯十六醚、聚氧乙烯油醚等之聚氧化乙烯烷醚類、聚氧乙烯辛基苯醚、聚氧乙烯壬基苯醚等之聚氧乙烯烷基芳醚類、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、EFTOP[註冊商標]EF301、同EF303、同EF352(三菱Materials電子化成股份公司製)、Megafac[註冊商標]F171、同F173、同R-30、同R-30N、同R-40、同R-40-LM(DIC股份公司製)、FluoradFC430、同FC431(住友3M股份公司製)、Asahiguard[註冊商標]AG710、Surflon[註冊商標]S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(旭硝子股份公司製)等之氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業股份公司製)。此等之界面活性劑,可單獨使用或組合2種以上使用。前述阻劑下層膜形成組成物包含界面活性劑時,其含量係相對於阻劑下層膜形成組成物之全固體成分,為0.0001~10重量%,較佳為0.01~5重量%。
本發明之阻劑下層膜形成組成物之固體成分,通常為0.1~70質量%,較佳為0.1~60質量%。固體成分係自阻劑下層膜形成組成物除去溶劑後之全成分的含有比例。固體成分中之本案化合物或反應產物之比例,依順序較佳為1~100質量%、1~99.9質量%、50~99.9質量%、50~95質量%、50~90質量%。
[其他的成分]
本發明之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。流變調整劑可有效地提高阻劑下層膜形成組成物之流動性。接著補助劑可有效地提高半導體基板或阻劑與下層膜之密著性。
吸光劑例如「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,可使用例如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,相對於阻劑下層膜形成組成物之全固體成分,通常以10質量%以下,較佳為以5質量%以下之比例來調配。
流變調整劑主要是提高阻劑下層膜形成組成物之流動性,特別是烘烤步驟中,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之目的而添加。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、馬來酸二正丁酯、馬來酸二乙酯、馬來酸二壬酯等之馬來酸衍生物、油酸甲酯、油酸丁酯、油酸四氫糠酯等之油酸衍生物、或硬脂酸正丁酯、硬脂酸甘油酯等之硬脂酸衍生物。此等之流變調整劑係相對於阻劑下層膜形成組成物之全固體成分,通常以未達30質量%之比例來調配。
接著補助劑主要是為了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之目的所添加的。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(三甲基矽基)脲、二甲基三甲基矽基胺、三甲基矽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、苯并三唑、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。此等之接著補助劑係相對於阻劑下層膜形成組成物之全固體成分,通常以未達5質量%,較佳為以未達2質量%之比例來調配。
[阻劑下層膜、經圖型化之基板之製造方法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所製造的阻劑下層膜、經圖型化之基板之製造方法及半導體裝置之製造方法。
(阻劑下層膜)
藉由將上述阻劑下層膜形成組成物塗佈於半導體基板上,經燒成可製造本發明之阻劑下層膜。
被塗佈本發明之阻劑下層膜形成組成物之半導體基板,可列舉例如矽晶圓、鍺晶圓、及砷化鎵、磷化銦、氮化鎵、氮化銦、氮化鋁等之化合物半導體晶圓。
使用表面形成有無機膜之半導體基板時,該無機膜可藉由例如ALD(原子層堆積)法、CVD(化學氣相堆積)法、反應性濺鍍法、離子被覆法、真空蒸鍍法、旋塗法(旋塗式玻璃:SOG)而形成。前述無機膜,可列舉例如多晶矽膜、氧化矽膜、氮化矽膜、BPSG(Boro-Phospho Silicate Glass)膜、氮化鈦膜、氮化氧化鈦膜、鎢膜、氮化鎵膜及砷化鎵膜。
這種半導體基板上藉由旋轉塗佈機、塗佈機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。然後,使用加熱板等之加熱手段,藉由烘烤形成阻劑下層膜。烘烤條件可自烘烤溫度100℃~400℃、烘烤時間0.3分鐘~60分鐘之中適宜選擇。較佳為烘烤溫度120℃~350℃、烘烤時間0.5分鐘~30分鐘,更佳為、烘烤溫度150℃~300℃、烘烤時間0.8分鐘~10分鐘。
所形成之阻劑下層膜之膜厚,例如0.001μm (1nm)~10μm,較佳為0.002μm(2nm)~1μm,更佳為0.005μm (5nm)~0.5μm(500nm)。烘烤時之溫度低於上述範圍時,變成交聯不充分。而烘烤時之溫度高於上述範圍時,有時阻劑下層膜因熱而分解。
(經圖型化之基板之製造方法)
經圖型化之基板之製造方法係經過以下的步驟。通常,在阻劑下層膜之上形成光阻層來製造。在阻劑下層膜上以習知的方法進行塗佈、燒成所形成的光阻,可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。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、由具有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的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的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JSR(股)製商品名V146G、Shipley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。
曝光係通過形成特定圖型用之遮罩(十字線)來進行,例如可使用i線、KrF準分子雷射、ArF準分子雷射、EUV(極紫外線)或EB(電子束)。顯影可使用鹼顯影液,可自顯影溫度5℃~50℃、顯影時間10秒~300秒來適宜選擇。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、氨水等之無機鹼類、乙基胺、n-丙基胺等之第一胺類、二乙基胺、二-n-丁基胺等之第二胺類、三乙基胺、甲基二乙基胺等之第三胺類、二甲基乙醇胺、三乙醇胺等之醇胺類、氫氧化四甲銨、氫氧化四乙銨、膽鹼等之第四級銨鹽、吡咯、哌啶等之環狀胺類等之鹼類的水溶液。此外,也可使用在上述鹼類之水溶液中適量添加異丙醇等之醇類、非離子系等之界面活性劑者。此等之中,較佳之顯影液為四級銨鹽,又更佳為氫氧化四甲銨及膽鹼。此外,此等之顯影液中也可加入界面活性劑等。也可取代鹼顯影液,以乙酸丁酯等之有機溶劑進行顯影,也可使用將光阻之未提昇鹼溶解速度的部分進行顯影的方法。經由上述步驟,可製造上述阻劑經圖型化的基板。
接著,以形成後的阻劑圖型作為遮罩,將前述阻劑下層膜進行乾蝕刻。此時,在使用之半導體基板表面形成前述無機膜時,使該無機膜之表面露出,在使用之半導體基板表面未形成前述無機膜時,使該半導體基板之表面露出。然後,經由將基板藉由習知的方法(乾蝕刻法等)對基板加工的步驟,可製造半導體裝置。
[實施例]
其次,舉實施例具體說明本發明之內容,但是本發明不限定於此等。
表示下述合成例所得之聚合物之重量平均分子量之測量用的裝置等。
裝置:東曹股份公司製HLC-8320GPC
GPC管柱:Shodex[註冊商標]・Asahipak[註冊商標](昭和電工(股))
管柱溫度:40℃
流量:0.35mL/分鐘
溶離液:四氫呋喃(THF)
標準試料:聚苯乙烯(東曹股份公司)
<合成例1>
投入依據專利公報(WO2017/208910)記載方法合成的甲基異三聚氰酸(Me-ICA)10.00g,碳酸鉀(關東化學(股)製)14.49g,烯丙基氯乙酸酯(Aldrich製)20.48g,N,N-二甲基甲醯胺(關東化學(股)製)40.00g,以60℃攪拌25小時。投入甲苯(關東化學(股)製)100.00g,然後進行過濾。於其中追加水100.00g,以50℃進行分液。對所得之有機層再追加水100.00g,以50℃進行分液。藉由將所得之有機層進行濃縮,得到式(М-1)表示之目的產物(甲基二烯丙乙酸酯異三聚氰酸:Me-DAAICA)20.51g、收率86.5%。確認此化合物之1
H NMR(500MHz,DMSO-d6
)為δ 5.92(m, 2H), 5.32(dd, 2H), 5.23(dd, 2H), 4.62(d, 4H), 4.66 (s, 4H), 3.23(s, 3H)。
<合成例2>
投入以合成例1所得之Me-DAAICA 20.51g、氯仿(關東化學(股)製)153.83g,於其中添加m-氯過苯甲酸(東京化成工業(股)製)38.52g。進行反應71小時,確認反應成為恆重(constant weight)。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,對所得之有機層中投入10重量%亞硫酸鈉(關東化學(股)製)205.10g。再度進行分液,對所得之有機層中投入5重量%碳酸氫鈉(關東化學(股)製)410.20g。然後,進行分液,對所得之有機層中加入水205.10g,進行2次洗淨。將有機層濃縮乾燥後,進行管柱純化,得到式(A-1)表示之目的產物(甲基二縮水甘油基乙酸酯異三聚氰酸:Me-DAGICA)10.46g、收率46.6%。測量此化合物之1
HNMR(500MHz,DMSO-d6
)為δ4.63(s, 4H), 4.49(dd, 2H), 3.94(dd, 2H), 3.23(m, 2H), 3.23(s, 3H), 2.79 (m, 2H), 2.65(m, 2H)。
<實施例1>
在合成例2所得之Me-DAGIA 4.00g、二硫代二乙酸(Dithiodiacetic Acid)2.40g、乙基三苯基溴化鏻0.20g中加入有丙二醇單甲醚26.42g之反應燒瓶中,在氮環境下,以100℃加熱攪拌24小時,得到相當於式(C-1)之反應產物。藉由GPC以聚苯乙烯換算所測量的重量平均分子量Mw為1800。又,式(C-1)中,a:b=100:120(莫耳比)。
加入相當於前述式(C-1)之反應產物溶液(固體成分為17.2重量%)5.59g、作為交聯酸觸媒之吡啶鎓三氟甲烷磺酸鹽0.04g、界面活性劑(DIC(股)製、品名:Megafac[商品名]R-40、氟系界面活性劑)0.001g、丙二醇單甲醚12.47g、丙二醇單甲醚乙酸酯1.90g,調製微影用阻劑下層膜形成組成物溶液。
<合成例3>
投入依據專利公報(WO2018/034323)記載方法合成的甲氧基甲基異三聚氰酸(MOM-ICA)27.50g,碳酸鉀(關東化學(股)製)32.93g,烯丙基氯乙酸酯(Aldrich製)46.55g,N,N-二甲基甲醯胺(關東化學(股)製)110.00g,以60℃攪拌4小時。因反應成為恆重,故投入甲苯(關東化學(股)製)257.00g進行過濾。於其中追加水257.00g,以50℃進行分液,藉由將所得之有機層進行濃縮,得到式(М-2)表示之目的產物(甲氧基甲基二烯丙乙酸酯異三聚氰酸:MOM-DAAICA)53.11g、收率90.5%。測量此化合物之1
H NMR(500MHz,DMSO-d6
)為δ5.91(m, 2H), 5.33(dd, 2H), 5.24(dd, 2H), 5.20(s, 2H), 4.65 (d, 4H), 4.64(s, 4H), 3.30(s, 3H)。
<合成例4>
投入以合成例3所得之MOM-DAAICA 53.11g、氯仿
(關東化學(股)製)398.33g,於其中添加m-氯過苯甲酸(東京化成工業(股)製)91.63g。進行反應76小時,確認反應成為恆重。反應結束後,追加氯仿(關東化學(股)製)531.10g、5重量%碳酸氫鈉(關東化學(股)製)1062.20g。進行分液,對所得之有機層中投入10重量%亞硫酸鈉(關東化學(股)製)531.10g。再度進行分液,對所得之有機層中投入5重量%碳酸氫鈉(關東化學(股)製)1062.20g。然後,進行分液,對所得之有機層中加入水531.11g,進行2次洗淨。將有機層濃縮乾燥後,進行管柱純化,得到式(A-7)表示之目的產物(甲氧基甲基二縮水甘油基乙酸酯異三聚氰酸:MOM-DAGICA)41.66g、收率72.2%。測量此化合物之1
H NMR(500MHz,DMSO-d6
)為δ5.20(s, 2H), 4.65(s, 4H), 4.49(dd, 2H), 3.95(dd, 2H), 3.31 (s, 3H), 3.22(m, 2H), 2.80(m, 2H), 2.66(m, 2H)。
<實施例2>
將在合成例4所得之MOM-DAGICA 5.50g、二硫代二乙酸2.90g、乙基三苯基溴化鏻0.25g中加入有丙二醇單甲醚8.69g之反應燒瓶中,在氮環境下,以70℃加熱攪拌24小時,得到相當於式(C-2)之反應產物。藉由GPC之聚苯乙烯換算所測量的重量平均分子量Mw為2300。又,式(C-2)中,a:b=100:120(莫耳比)。
加入相當於前述式(C-2)之反應產物溶液(固體成分為18.7重量%)5.13g、作為交聯酸觸媒之吡啶鎓三氟甲烷磺酸鹽0.04g、界面活性劑(DIC(股)製、品名:Megafac[商品名]R-40、氟系界面活性劑)0.001g、丙二醇單甲醚12.93g、丙二醇單甲醚乙酸酯1.90g,調製微影用阻劑下層膜形成組成物溶液。
<合成例5>
投入依據美國專利第3230220號說明書所記載方法合成的三羧基甲基異三聚氰酸(TAICA)38.70g、N-甲基-2-吡咯烷酮(關東化學(股)製)300.00g,烯丙基溴化物(東京化成工業(股)製)70.91g、碳酸鉀(關東化學(股)製)79.38g,昇溫至80-90℃。然後,反應2小時,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,以水580.50g水洗3次。將有機層濃縮乾燥後,投入乙醇(關東化學(股)製)387.00g,在20-30℃下攪拌30分鐘。攪拌結束後,進行過濾,將所得之結晶進行乾燥,得到式(М-3)表示之目的產物(三烯丙基乙酸酯異三聚氰酸:TAAICA)44.32g、收率85.2%。
<合成例6>
投入以合成例5合成之TAAICA 44.32g、氯仿(關東化學(股)製)443.20g,其中加入m-氯過苯甲酸(東京化成工業(股)製)125.06g。進行47小時反應。反應結束後,追加氯仿(關東化學(股)製)88.64g。再以5%碳酸氫鈉(關東化學(股)製)886.40g洗淨。接著,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洗淨,再以水443.20g洗淨2次。濃縮後進行管柱純化。管柱純化後,得到式(М-2)表示之目的產物(三縮水甘油基乙酸酯異三聚氰酸:TAGICA)41.31g、收率83.7%。
<實施例3>
在合成例6所得之TAGICA 9.00g、二硫代二乙酸6.99g、乙基三苯基溴化鏻0.53g中加入有丙二醇單甲醚66.11g之反應燒瓶中,在氮環境下,以70℃加熱攪拌23小時,得到相當於式(C-3)之反應產物。藉由GPC之聚苯乙烯換算所測量的重量平均分子量Mw為3000。又,式(C-3)中,a:b=100:200(莫耳比)。
加入相當於前述式(C-3)之反應產物溶液(固體成分為11.56重量%)8.31g、作為交聯酸觸媒之吡啶鎓三氟甲烷磺酸鹽0.04g、界面活性劑(DIC(股)製、品名:Megafac[商品名]R-40、氟系界面活性劑)0.001g、丙二醇單甲醚9.75g、丙二醇單甲醚乙酸酯1.90g,調製微影用阻劑下層膜形成組成物溶液。
<比較例1>
在單甲基二縮水甘油基異三聚氰酸(製品名:Me-DGIC、四國化成工業(股)製、50重量%丙二醇單甲醚溶液)12.00g、二硫代二乙酸5.26g、乙基三苯基溴化鏻0.45g中加入有丙二醇單甲醚1.80g之反應燒瓶中,在氮環境下,以70℃加熱攪拌21小時。所得之反應產物溶液中加入丙二醇單甲醚39.01g進行稀釋,得到相當於式(D-1)之反應產物。藉由GPC之聚苯乙烯換算所測量的重量平均分子量Mw為1700。又,式(D-1)中,a:b=100:120(莫耳比)。
加入相當於前述式(D-1)之反應產物溶液(固體成分為17.8重量%)5.41g、作為交聯酸觸媒之吡啶鎓三氟甲烷磺酸鹽0.04g、界面活性劑(DIC(股)製、品名:Megafac[商品名]R-40、氟系界面活性劑)0.001g、丙二醇單甲醚12.65g、丙二醇單甲醚乙酸酯1.90g,調製微影用阻劑下層膜形成組成物溶液。
<比較例2>
在1,3,5-三(2,3-環氧基丙基)異三聚氰酸(製品名:TEPIC-SS、日產化學工業(股)製)4.00g、二硫代二乙酸6.09g、乙基三苯基溴化鏻0.37g中加入有丙二醇單甲醚10.46g之反應燒瓶中,在氮環境下,以65℃加熱攪拌22小時。在所得之反應產物溶液中加入丙二醇單甲醚31.39g進行稀釋,得到相當於式(D-2)之反應產物。藉由GPC之聚苯乙烯換算所測量的重量平均分子量Mw為2800。又,式(D-2)中,a:b=100:250(莫耳比)。
加入相當於前述式(D-2)之反應產物溶液(固體成分為13.0重量%)7.40g、作為交聯酸觸媒之吡啶鎓三氟甲烷磺酸鹽0.04g、界面活性劑(DIC(股)製、品名:Megafac[商品名]R-40、氟系界面活性劑)0.001g、丙二醇單甲醚10.66g、丙二醇單甲醚乙酸酯1.90g,調製微影用阻劑下層膜形成組成物溶液。
[阻劑溶劑耐性之評價]
使用塗佈機、顯影機(coater developer)(CLEAN TRACK ACT-8,東京威力科創(股)製),在矽晶圓上塗佈(旋轉塗佈)以實施例1至實施例3及比較例1至比較例2所調製的微影用阻劑下層膜形成組成物使成為膜厚100nm左右,在烘烤單元中以215℃或250℃、60秒鐘進行烘烤(燒成)。其次,為了確認在晶圓上所製膜之阻劑下層膜的阻劑溶劑耐性,使用塗佈機、顯影機將OK73稀釋劑(東京應化工業(股)製、丙二醇單甲醚/丙二醇單甲醚乙酸酯=70/30混合溶劑)在成膜之阻劑下層膜上浸漬1分鐘,旋轉脫水(spin-dry)後,以100℃烘烤30秒鐘。使用光干涉式膜厚計(Lamda Ace VM-3210、(股)SCREEN製)測量浸漬混合溶劑之前後之阻劑下層膜的膜厚。
阻劑溶劑耐性之評價係由((溶劑浸漬前之膜厚)-(溶劑浸漬後之膜厚))÷(溶劑浸漬前之膜厚)×100之計算式,評價以溶劑浸漬所除去之阻劑下層膜的膜厚減少率(%)。又,膜厚減少率為約1%以下時,評價為具有充分的阻劑溶劑耐性。此阻劑下層膜之膜厚減少率(%)如[表1]所示。
由上述結果,實施例1至實施例3對於阻劑溶劑,展現充分的溶劑耐性,故適合作為阻劑下層膜。
[光學常數之評價]
藉由旋轉塗佈機,於矽晶圓上塗佈以實施例1至實施例3及比較例1至比較例2所調製的微影用阻劑下層膜形成組成物,使成為膜厚50nm左右,在加熱板上以215℃或250℃烘烤(燒成)60秒鐘。使用分光橢圓測厚儀(VUV-VASE、J.A.Woolam製)測量所得之阻劑下層膜在波長193nm下之n值(折射率)及k值(衰減係數(damping coefficient))其結果如表2所示。
[蝕刻選擇比之評價]
在矽晶圓上塗佈以實施例1至實施例3及比較例1至比較例2所調製的微影用阻劑下層膜形成組成物,使成為膜厚130nm左右,然後在加熱板上以215℃或250℃、烘烤(燒成)60秒鐘。將所得之阻劑下層膜使用乾蝕刻裝置(RIE-10NR、Samco(股)製),藉由氮氣之乾蝕刻進行60秒鐘,測量阻劑下層膜之乾蝕刻速度。
在矽晶圓上塗佈半導體微影用抗反射塗覆劑(製品名:DUV30J、日產化學工業(股)製),使成為膜厚150nm左右,然後在加熱板上,以215℃、烘烤(燒成)60秒鐘。將所得之被膜使用乾蝕刻裝置(RIE-10NR、Samco(股)製),藉由氮氣之乾蝕刻進行60秒鐘,測量阻劑下層膜之乾蝕刻速度。
以半導體微影用抗反射塗覆劑(DUV30J)之乾蝕刻速度作為1.00時,由實施例1至實施例3及比較例1至比較例2所調製的微影用阻劑下層膜形成組成物所得之阻劑下層膜之乾蝕刻速度之比(蝕刻選擇比)如[表2]所示。
由上述結果,因實施例1至實施例3具有對波長193nm之適度的n/k值,故作為微影用阻劑下層膜具有抑制由基底基板之反射之抗反射塗覆劑的機能。又,實施例1至實施例3,相較於比較例1至比較例2,具有充分高的蝕刻選擇比,故藉由本案發明所得之微影用阻劑下層膜形成組成物,可縮短阻劑下層膜之乾蝕刻時的蝕刻時間,以乾蝕刻除去阻劑下層膜時,可抑制阻劑膜厚減少之不佳的現象。此外,可縮短乾蝕刻時間,可降低阻劑下層膜對基底基板不佳的蝕刻受傷,因此可特別適合作為阻劑下層膜使用。
[產業上之可利用性]
本發明之阻劑下層膜形成組成物,特別是提供具有高乾蝕刻速度的阻劑下層膜。
Claims (14)
- 一種下述式(1)表示之化合物,
- 如請求項1之化合物,其中前述式(1)中,X為式(4)表示。
- 如請求項2之化合物,其中前述式(1)中,n1及n2為1,R3為可被氧原子中斷之碳原子數1至5之烷基或以式(5)表示。
- 一種阻劑下層膜形成組成物,其係包含藉由如下述式(1)表示之化合物
- 如請求項4之阻劑下層膜形成組成物,其中前述環氧加成物形成化合物為選自由含羧酸之化合物、含羧酸酐之化合物、含羥基之化合物、含硫醇基之化合物、含胺基之化合物及含醯亞胺基之化合物所成群之至少1種的化合物。
- 如請求項4之阻劑下層膜形成組成物,其中前述環氧加成物形成化合物為含羧酸之化合物或含硫醇基之化合物。
- 如請求項6之阻劑下層膜形成組成物,其中前述含羧酸之化合物為含有至少1個以上之硫原子的二羧酸。
- 如請求項7之阻劑下層膜形成組成物,其中前述有至少1個以上之硫原子的二羧酸為脂肪族二羧酸。
- 如請求項4至請求項8中任一項之阻劑下層膜形成組成物,其係進一步含有交聯觸媒。
- 如請求項4至請求項8中任一項之阻劑下層膜形成組成物,其係進一步含有交聯劑。
- 如請求項4至請求項8中任一項之阻劑下層膜形成組成物,其係進一步含有界面活性劑。
- 一種阻劑下層膜,其係由如請求項4至請求項11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。
- 一種經圖型化之基板的製造方法,其係包含下步驟:在半導體基板上塗佈如請求項4至請求項11中任一項之阻劑下層膜形成組成物,經烘烤形成阻劑下層膜的步驟,在前述阻劑下層膜上塗佈阻劑,經烘烤形成阻劑膜的步驟,將以前述阻劑下層膜與前述阻劑被覆之半導體基板進行曝光的步驟,及將曝光後之前述阻劑膜顯影,進行圖型化的步驟。
- 一種半導體裝置之製造方法,其係包含下步驟:在半導體基板上形成如請求項4至請求項11中任一項之阻劑下層膜形成組成物所成之阻劑下層膜的步驟,在前述阻劑下層膜上形成阻劑膜的步驟,藉由對阻劑膜照射光或電子束與其後之顯影,形成阻劑圖型的步驟,經由所形成之前述阻劑圖型,藉由蝕刻前述阻劑下層膜,形成經圖型化的阻劑下層膜的步驟,及藉由經圖型化之前述阻劑下層膜,將半導體基板進行加工的步驟。
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- 2019-06-18 JP JP2020527417A patent/JP7355012B2/ja active Active
- 2019-06-18 KR KR1020207035814A patent/KR20210024461A/ko not_active Application Discontinuation
- 2019-06-19 TW TW108121194A patent/TWI823950B/zh active
Patent Citations (2)
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US3787405A (en) * | 1970-11-18 | 1974-01-22 | Ciba Geigy Ag | Diglycidyl compounds containing a n-heterocyclic ring |
JPH0881461A (ja) * | 1994-09-12 | 1996-03-26 | Nissan Chem Ind Ltd | 新規エポキシ化合物及びその製造方法 |
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JPWO2020004122A1 (ja) | 2021-08-05 |
US20210271168A1 (en) | 2021-09-02 |
WO2020004122A1 (ja) | 2020-01-02 |
KR20210024461A (ko) | 2021-03-05 |
JP7355012B2 (ja) | 2023-10-03 |
CN112313226A (zh) | 2021-02-02 |
TW202012398A (zh) | 2020-04-01 |
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