TWI610955B - 二芳基胺酚醛清漆樹脂 - Google Patents
二芳基胺酚醛清漆樹脂 Download PDFInfo
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- TWI610955B TWI610955B TW101135906A TW101135906A TWI610955B TW I610955 B TWI610955 B TW I610955B TW 101135906 A TW101135906 A TW 101135906A TW 101135906 A TW101135906 A TW 101135906A TW I610955 B TWI610955 B TW I610955B
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
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- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
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- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
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- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
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- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
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- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
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- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
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- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
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- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- 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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Description
本發明係關於苯基萘基胺酚醛清漆樹脂等之二芳基胺酚醛清漆樹脂者。進而關於可用於使用苯基萘基胺酚醛清漆樹脂等之二芳基胺酚醛清漆樹脂、使半導體基板加工時之微影術用阻劑底層膜形成組成物、以及使用該阻劑底層膜形成組成物的阻劑圖型形成法、及半導體裝置之製造方法者。又,關於使用苯基萘基胺酚醛清漆樹脂的在可見光區域之透明性的高折射率膜者。
以往的半導體裝置之製造中、進行使用光阻劑組成物的微影術之微細加工。前述微細加工係在矽晶圓等之被加工基板上,形成光阻劑組成物的薄膜,於其上透過描繪有半導體裝置圖型的遮罩圖型,照射紫外線等之活性光線,顯影使得到的光阻劑圖型作為保護膜將矽晶圓等之被加工基板進行蝕刻處理之加工法。然而,近年、半導體裝置的高積體度化進展、使用的活性光線亦有至KrF準分子雷射(248nm)~ArF準分子雷射(193nm)短波長化的傾向。伴隨此,活性光線來自基板之漫反射或駐波的影響為大問題。因此,變得廣為探討在光阻劑與被加工基板間設置防反射膜(Bottom Anti-Reflective Coating、BARC)之方法。
今後、若阻劑圖型之微細化進展,產生解像度之問題
或阻劑圖型在顯影後倒塌之問題,期望阻劑的薄膜化。因此,在基板加工難以得到充分的阻劑圖型膜厚,不僅阻劑圖型,在阻劑與加工之半導體基板間作成的阻劑底層膜亦變得需要使具有作為基板加工時的遮罩機能之製程。作為如此之製程用的阻劑底層膜,與以往高蝕刻速度性(蝕刻速度快)阻劑底層膜相異,要求具有與阻劑接近的乾蝕刻速度之選擇比之微影術用阻劑底層膜、具有比阻劑小的乾蝕刻速度之選擇比之微影術用阻劑底層膜或比半導體基板小的乾蝕刻速度之選擇比之微影術用阻劑底層膜。
上述阻劑底層膜用的聚合物,可舉例如以下者。
如使用聚乙烯基咔唑的阻劑底層膜形成組成物(專利文獻1、專利文獻2、及專利文獻3做為參考)。
揭示使用芴酚酚醛清漆樹脂的阻劑底層膜形成組成物(例如專利文獻4做為參考)。
揭示使用芴萘酚酚醛清漆樹脂的阻劑底層膜形成組成物(例如專利文獻5做為參考)。
揭示含有以芴酚與芳基伸烷基為重複單位的樹脂之阻劑底層膜形成組成物(例如專利文獻6、專利文獻7做為參考)。
揭示使用苯基萘基胺與乙醛的酚醛清漆樹脂(專利文獻8做為參考)。
〔專利文獻1〕日本特開平2-293850號公報
〔專利文獻2〕日本特開平1-154050號公報
〔專利文獻3〕日本特開平2-22657號公報
〔專利文獻4〕日本特開2005-128509號公報
〔專利文獻5〕日本特開2007-199653號公報
〔專利文獻6〕日本特開2007-178974號公報
〔專利文獻7〕美國專利第7378217號說明書
〔專利文獻8〕日本特開2007-297540號公報
本發明提供新穎苯基萘基胺酚醛清漆樹脂等之二芳基胺酚醛清漆樹脂。進而本發明提供用於使用苯基萘基胺酚醛清漆樹脂等之二芳基胺酚醛清漆樹脂的半導體裝置製造的微影術製程用的阻劑底層膜形成組成物。又本發明提供不與阻劑層互混,可得到優異阻劑圖型,具有與阻劑接近的乾蝕刻速度之選擇比的微影術用阻劑底層膜、具有比阻劑小的乾蝕刻速度之選擇比的微影術用阻劑底層膜或具有比半導體基板小的乾蝕刻速度之選擇比的微影術用阻劑底層膜。又本發明可賦予248nm、193nm、157nm等之波長的照射光用於微細加工時,有效吸收來自基板的反射光之性能。進而、本發明提供使用阻劑底層膜形成組成物的阻劑圖型之形成法。接著、提供亦兼具耐熱性的形成阻劑底層膜用之阻劑底層膜形成組成物。
又,提供使用苯基萘基胺酚醛清漆樹脂的特異性質、
在可見光區域之透明性高折射率膜及使用其之電子裝置。
本發明,第1觀點為含有下述式(1):
(式(1)中,Ar1、及Ar2各自表示苯環、或萘環,R1及R2各自為此等環上的氫原子之取代基,表示鹵素基、硝基、胺基、羥基、碳原子數1乃至10之烷基、碳原子數2乃至10之烯基、碳原子數6乃至40之芳基、及彼等之組合所成群中選出、且該烷基、該烯基及該芳基為可含有醚鍵結、酮鍵結、或者酯鍵結的有機基,R3為氫原子、碳原子數1乃至10之烷基、碳原子數2乃至10之烯基、碳原子數6乃至40之芳基、及彼等之組合所成群中選出、且該烷基、該烯基及芳基為可含有醚鍵結、酮鍵結、或者酯鍵結的有機基,R4為碳原子數6乃至40之芳基及雜環基所成群中選出、且該芳基及該雜環基為可以鹵素基、硝基、胺基、碳原子數1乃至10之烷基、碳原子數1乃至10之烷氧基、碳原子數6乃至40之芳基、甲醯基、羧基、或羥基取代
的有機基,R5為氫原子、碳原子數1乃至10之烷基、碳原子數6乃至40之芳基、及雜環基所成群中選出、且該烷基、該芳基及該雜環基為可以鹵素基、硝基、胺基、或者羥基取代的有機基,接著R4與R5可與彼等鍵結的碳原子一起形成環。n1及n2各自為0乃至3之整數。)所表示的單位構造(A)之聚合物、第2觀點,上述式(1)的R5為氫原子,R4為可經取代的苯基、萘基、蒽基、或芘基之第1觀點記載之聚合物、第3觀點,上述式(1)的R3為氫原子或苯基之第1觀點或第2觀點記載之聚合物、第4觀點,上述單位構造(A)中,含有Ar1與Ar2中任一者為苯環,另一者為萘環之單位構造(a1)的第1觀點乃至第3觀點中任一記載之聚合物、第5觀點,上述單位構造(A)中,含有Ar1與Ar2皆為苯環的單位構造(a2)的第1觀點乃至第3觀點中任一記載之聚合物、第6觀點,含有第4觀點記載之單位構造(a1)與第5觀點記載之單位構造(a2)之共聚合物的聚合物、第7觀點,含有第1觀點記載之式(1)之單位構造(A)與下述式(2)之單位構造(B):
(式(2)中,R6為碳原子數6乃至40之芳基及雜環基所成群中選出、且該芳基及該雜環基為可以鹵素基、硝基、胺基、碳原子數1乃至10之烷基、碳原子數1乃至10之烷氧基、碳原子數6乃至40之芳基、甲醯基、羧基、或羥基取代的有機基,R7為氫原子、碳原子數1乃至10之烷基、碳原子數6乃至40之芳基、及雜環基所成群中選出、且該烷基、該芳基及該雜環基為可以鹵素基、硝基、胺基、或者羥基取代的有機基,接著R6與R7可與彼等鍵結的碳原子一起形成環。)之共聚合物的聚合物、第8觀點,含有第4觀點記載之單位構造(a1)與第7觀點記載之單位構造(B)之共聚合物的聚合物、第9觀點,含有第1觀點乃至第8觀點中任一記載之聚合物之微影術用阻劑底層膜形成組成物、第10觀點,再含有交聯劑的第9觀點記載之阻劑底層膜形成組成物、第11觀點,再含有酸及/或酸產生劑的第9觀點或第10觀點記載之阻劑底層膜形成組成物、第12觀點,將第9觀點乃至第11觀點中任一記載之
阻劑底層膜形成組成物塗佈於半導體基板上並進行燒成而得到的阻劑底層膜、第13觀點,包含在半導體基板上以第9觀點乃至第11觀點中任一記載之阻劑底層膜形成組成物形成底層膜之步驟、於其上形成阻劑膜之步驟、經光或電子線之照射與顯影形成阻劑圖型之步驟、經該阻劑圖型使該底層膜進行蝕刻之步驟、及透過經圖型化的該底層膜加工半導體基板之步驟的半導體裝置之製造方法、及、第14觀點,包含在半導體基板以第9觀點乃至第11觀點中任一記載之阻劑底層膜形成組成物形成底層膜之步驟、於其上形成硬遮罩之步驟、再於其上形成阻劑膜之步驟、經光或電子線之照射與顯影形成阻劑圖型之步驟、經該阻劑圖型蝕刻該硬遮罩之步驟、透過經圖型化的該硬遮罩蝕刻該底層膜之步驟、及透過經圖型化的該底層膜加工半導體基板之步驟的半導體裝置之製造方法。
藉由本發明的阻劑底層膜形成組成物,阻劑底層膜的上層部與被覆於其上之層不產生互混、可形成良好的阻劑的圖型形狀。
本發明的阻劑底層膜形成組成物,亦可賦予有效抑制來自基板之反射的性能、亦一併具有作為曝光光之防反射膜的效果。
藉由本發明的阻劑底層膜形成組成物,可提供具有與
阻劑接近的乾蝕刻速度之選擇比、比阻劑小的乾蝕刻速度之選擇比或比半導體基板小的乾蝕刻速度之選擇比之優異阻劑底層膜。
伴隨阻劑圖型之微細化,防止阻劑圖型在顯影後倒塌而進行阻劑的薄膜化。在如此的薄膜阻劑,有使阻劑圖型在蝕刻製程轉印至該底層膜、將該底層膜作為遮罩進行基板加工之製程、或使阻劑圖型在蝕刻製程轉印至該底層膜、進而重複將轉印至底層膜的圖型以不同氣體組成轉印至該底層膜的行程、最終進行基板加工的製程。本發明的阻劑底層膜及其形成組成物在該製程有效,使用本發明的阻劑底層膜加工基板時,為對加工基板(例如基板上的熱氧化矽膜、氮化矽膜、聚矽膜等)具有充分蝕刻耐性者。
接著、本發明的阻劑底層膜可用作為平坦化膜、阻劑底層膜、阻劑層的污染防止膜、具有乾蝕刻選擇性的膜。藉由此,變得可使半導體製造的微影術製程中阻劑圖型形成容易、且高精度地進行。
有使本發明的阻劑底層膜形成組成物之阻劑底層膜形成於基板上、於其上形成硬遮罩、於其上形成阻劑膜,藉由曝光與顯影形成阻劑圖型,使阻劑圖型轉印於硬遮罩,將轉印於硬遮罩的阻劑圖型轉印至阻劑底層膜,以該阻劑底層膜進行半導體基板加工之製程。在該製程,有硬遮罩為含有有機聚合物或無機聚合物與溶劑的塗佈型之組成物進行的情形、與以無機物的真空蒸鍍進行之情形。在無機物(例如氮化氧化矽)之真空蒸鍍,蒸鍍物在阻劑底層膜
表面堆積,但此時,阻劑底層膜表面的溫度上升至400℃左右。因在本發明使用的聚合物為含有苯基萘基胺酚醛清漆等之二芳基胺酚醛清漆系之單位構造的聚合物,耐熱性極高、即使蒸鍍物的堆積亦不產生熱劣化。
又本發明的苯基萘基胺酚醛清漆樹脂,除上述目的外,在可視光區域的透明性與耐熱性優異、具有高折射率,且對種種溶劑之溶解性優異。利用此等之特性,可應用在液晶顯示元件的保護膜、TFT陣列平坦化膜、彩色濾光片等之保護膜、間隔件材、EL顯示器之光取出提升膜、攝影元件之光攝入提升層、LED元件中光取出提升層等廣泛的光學構件。
本發明為含有式(1)所示之單位構造(A)之聚合物。
本發明使用的聚合物,重量平均分子量為600乃至1000000、或600乃至200000。
本發明使用的聚合物為含有式(1)所示之重複單位構造(A)。
式(1)中,Ar1、及Ar2各自表示苯環、萘環,R1及R2各自為此等環上的氫原子之取代基,表示鹵素基、硝基、胺基、羥基、碳原子數1乃至10之烷基、碳原子數2乃至10之烯基、碳原子數6乃至40之芳基、及彼等之組合所成群中選出、且該烷基、該烯基及該芳基為可含有醚
鍵結、酮鍵結、或者酯鍵結的有機基,R3為氫原子、碳原子數1乃至10之烷基、碳原子數2乃至10之烯基、碳原子數6乃至40之芳基、及彼等之組合所成群中選出、且該烷基、該烯基及該芳基為可含有醚鍵結、酮鍵結、或者酯鍵結的有機基,R4為碳原子數6乃至40之芳基及雜環基所成群中選出、且該芳基及該雜環基為可以鹵素基、硝基、胺基、碳原子數1乃至10之烷基、碳原子數1乃至10之烷氧基、碳原子數6乃至40之芳基、甲醯基、羧基、或羥基取代的有機基,R5為氫原子、碳原子數1乃至10之烷基、碳原子數6乃至40之芳基、及雜環基所成群中選出、且該烷基、該芳基及該雜環基為可以鹵素基、硝基、胺基、或者羥基取代的有機基,接著R4與R5可與彼等鍵結的碳原子一起形成環。n1及n2各自為0乃至3之整數。
上述鹵素基,可舉例如氟原子、氯原子、溴原子、碘原子。
碳原子數1乃至10之烷基,可舉例如甲基、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乃至10之烯基,可舉例如乙烯基、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、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。
上述碳原子數1乃至10之烷氧基,例如甲氧基、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-己基氧基、1-甲基-n-戊基氧基、2-甲基-n-戊基氧基、3-甲基-n-戊基氧基、4-甲基-n-戊基氧基、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。
上述碳原子數6乃至40之芳基,可舉例如苯基、o-甲基苯基、m-甲基苯基、p-甲基苯基、o-氯苯基、m-氯苯基、p-氯苯基、o-氟苯基、p-氟苯基、o-甲氧基苯基、p-甲氧基苯基、p-硝基苯基、p-氰苯基、α-萘基、β-萘基、o-聯苯基、m-聯苯基、p-聯苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基及9-菲基、芘基等。
上述雜環基以由含有氮、硫、氧之5乃至6員環之雜
環所成的有機基為佳,例如吡咯基、呋喃基、噻吩基、咪唑基、噁唑基、噻唑基、吡唑基、異噁唑基、異噻唑基、吡啶基等。
其中以用於高折射率材料的含硫雜環基較佳。
上述式(1)所表示的單位構造(A)可為R5為氫原子,R4為可經取代的苯基、萘基、蒽基、或芘基。
又,上述式(1)所表示的單位構造(A)可為R3為氫原子或苯基。
在本發明上述單位構造(A)中,可使用Ar1與Ar2中任一者為苯環,另一者為萘環之單位構造(a1)。又,上述單位構造(A)中,可使用Ar1與Ar2皆為苯環的單位構造(a2)。
本發明的聚合物可為含上述單位構造(a1)與上述單位構造(a2)之共聚合物的聚合物。
接著可為含式(1)所示之單位構造(A)與式(2)所示之單位構造(B)之共聚合物。
上述單位構造(B)中,R6為碳原子數6乃至40之芳基及雜環基所成群中選出、且該芳基及該雜環基為可以鹵素基、硝基、胺基、碳原子數1乃至10之烷基、碳原子數1乃至10之烷氧基、碳原子數6乃至40之芳基、甲醯基、羧基、或羥基取代的有機基,R7為氫原子、碳原子數1乃至10之烷基、碳原子數6乃至40之芳基、及雜環基所成群中選出、且該烷基、該芳基及該雜環基為可以鹵素基、硝基、胺基、或者羥基取代的有機基,接著R6與
R7可與彼等鍵結的碳原子一起形成環。
此等之取代基或烷基、芳基、雜環基可使用上述例示。
本發明的聚合物可為含上述單位構造(a1)與上述單位構造(B)之共聚合物。
本發明使用的聚合物,例如以下例示。
本發明中使用咔唑類之場合,例如咔唑、N-甲基咔唑、N-乙基咔唑、1,3,6,8-四硝基咔唑、3,6-二胺基咔唑、
3,6-二溴-9-乙基咔唑、3,6-二溴-9-苯基咔唑、3,6-二溴咔唑、3,6-二氯咔唑、3-胺基-9-乙基咔唑、3-溴-9-乙基咔唑、4,4’-雙(9H-咔唑-9-基)聯苯基、4-環氧丙基咔唑、4-羥基咔唑、9-(1H-苯並三唑-1-基甲基)-9H-咔唑、9-乙醯基-3,6-二碘咔唑、9-苯甲醯基咔唑、9-苯甲醯基咔唑-6-二羧基醛、9-苄基咔唑-3-羧基醛、9-甲基咔唑、9-苯基咔唑、9-乙烯基咔唑、咔唑鉀、咔唑-N-羰基氯化物、N-乙基咔唑-3-羧基醛、N-((9-乙基咔唑-3-基)亞甲基)-2-甲基-1-吲哚啉基胺等,此等可單獨使用或2種以上組合使用。
在本發明使用三苯基胺類之場合,例如三苯基胺或取代三苯基胺,取代基,可舉例如上述鹵素基、硝基、胺基、羥基、碳原子數1乃至10之烷基、碳原子數2乃至10之烯基、碳原子數6乃至40之芳基、或亦可含醚鍵結、酮鍵結、或者酯鍵結的彼等之組合。
本發明的聚合物的製造使用的醛類,可舉例如甲醛、多聚甲醛、乙醛、丙基醛、丁基醛、異丁基醛、戊醛、已醛、2-甲基丁基醛、己基醛、十一烷醛、7-甲氧基-3、7-二甲基辛基醛、環己烷醛、3-甲基-2-丁基醛、乙二醛、丙二醛、丁二醛、戊二醛、戊二醛、己二醛等之飽和脂肪族醛類、丙烯醛、甲基丙烯醛等之不飽和脂肪族醛類、呋喃甲醛、吡啶醛、噻吩醛等之雜環式醛類、苯甲醛、萘並醛、蒽羧基醛、苯基苯甲醛、大茴香醛、對苯二甲醛、芘羧基醛、菲基醛、水楊醛、苯基乙醛、3-苯基丙醛、甲苯
基醛、(N,N-二甲基胺基)苯甲醛、乙醯氧基苯甲醛等之芳香族醛類等。尤以使用芳香族醛為佳。
又,作為本發明的聚合物的製造使用的酮類,為二芳基酮類,可舉例如二苯基酮、苯基萘基酮、二萘基酮、苯基甲苯基酮、二甲苯基酮、9-芴酮等。
本發明使用的聚合物為二芳基胺等之胺類與醛類或酮類進行縮合得到的酚醛清漆樹脂(相當式(1))。
在該縮合反應,相對二芳基胺等之胺類的苯基1當量,醛類或酮類可以0.1乃至10當量的比例使用。
上述縮合反應可使用的酸觸媒,例如使用硫酸、磷酸、過氯酸等之礦酸類、p-甲苯磺酸、p-甲苯磺酸一水合物等之有機磺酸類、甲酸、草酸等之羧酸類。酸觸媒之使用量因使用酸類的種類而有種種選擇。通常相對咔唑類、或咔唑類與三苯基胺類之合計100質量份為0.001乃至10000質量份、較佳為0.01乃至1000質量份、更佳為0.1乃至100質量份。
上述縮合反應雖亦可以無溶劑進行,但通常使用溶劑進行。作為溶劑,不阻礙反應者皆可使用。例如四氫呋喃、二噁烷等之環狀醚類。又,使用之酸觸媒為例如甲酸般液狀者則亦可兼具作為溶劑之角色。
縮合時的反應溫度,通常為40℃乃至200℃。反應時間因反應溫度而有種種選擇,但通常為30分鐘乃至50小時左右。
如以上般得到的聚合物的重量平均分子量Mw通常為
600乃至1000000、或600乃至200000。
本發明為含上述聚合物之微影術用阻劑底層膜、及可用作為形成該底層膜用之微影術用阻劑底層膜形成組成物。
本發明中微影術用阻劑底層膜形成組成物為含有上述聚合物與溶劑。接著、可含有交聯劑與酸、因應必要可含有酸產生劑、界面活性劑等之添加劑。該組成物的固形分為0.1乃至70質量%、或0.1乃至60質量%。固形分為由阻劑底層膜形成組成物除去溶劑的全成分之含有比例。固形分中可含有上述聚合物1乃至100質量%、或1乃至99.9質量%、或50乃至99.9質量%之比例。
上述聚合物可以其他聚合物在全聚合物中混合30質量%以內使用。
彼等聚合物,可舉例如聚丙烯酸酯化合物、聚甲基丙烯酸酯化合物、聚丙烯醯胺化合物、聚甲基丙烯基醯胺化合物、聚乙烯基化合物、聚苯乙烯化合物、聚馬來醯亞胺化合物、聚馬來酸酐、及聚丙烯腈化合物。
聚丙烯酸酯化合物的原料單體,可舉例如甲基丙烯酸酯、乙基丙烯酸酯、異丙基丙烯酸酯、苄基丙烯酸酯、萘基丙烯酸酯、蒽基丙烯酸酯、蒽基甲基丙烯酸酯、苯基丙烯酸酯、2-羥基乙基丙烯酸酯、2-羥基丙基丙烯酸酯、2,2,2-三氟乙基丙烯酸酯、4-羥基丁基丙烯酸酯、異丁基丙烯酸酯、tert-丁基丙烯酸酯、環己基丙烯酸酯、異冰片基丙烯酸酯、2-甲氧基乙基丙烯酸酯、甲氧基三乙二醇丙
烯酸酯、2-乙氧基乙基丙烯酸酯、四氫糠基丙烯酸酯、3-甲氧基丁基丙烯酸酯、2-甲基-2-金剛烷基丙烯酸酯、2-乙基-2-金剛烷基丙烯酸酯、2-丙基-2-金剛烷基丙烯酸酯、2-甲氧基丁基-2-金剛烷基丙烯酸酯、8-甲基-8-三環癸基丙烯酸酯、8-乙基-8-三環癸基丙烯酸酯、及5-丙烯醯基氧基-6-羥基降冰片烯-2-羧酸-6-內酯等。
聚甲基丙烯酸酯化合物的原料單體,可舉例如乙基甲基丙烯酸酯、正丙基甲基丙烯酸酯、正戊基甲基丙烯酸酯、環己基甲基丙烯酸酯、苄基甲基丙烯酸酯、萘基甲基丙烯酸酯、蒽基甲基丙烯酸酯、蒽基甲基甲基丙烯酸酯、苯基甲基丙烯酸酯、2-苯基乙基甲基丙烯酸酯、2-羥基乙基甲基丙烯酸酯、2-羥基丙基甲基丙烯酸酯、2,2,2-三氟乙基甲基丙烯酸酯、2,2,2-三氯乙基甲基丙烯酸酯、甲基丙烯酸酯、異丁基甲基丙烯酸酯、2-乙基己基甲基丙烯酸酯、異癸基甲基丙烯酸酯、正月桂基甲基丙烯酸酯、正硬脂醯基甲基丙烯酸酯、甲氧基二乙二醇甲基丙烯酸酯、甲氧基聚乙二醇甲基丙烯酸酯、四氫糠基甲基丙烯酸酯、異冰片基甲基丙烯酸酯、tert-丁基甲基丙烯酸酯、異硬脂醯基甲基丙烯酸酯、正丁氧基乙基甲基丙烯酸酯、3-氯-2-羥基丙基甲基丙烯酸酯、2-甲基-2-金剛烷基甲基丙烯酸酯、2-乙基-2-金剛烷基甲基丙烯酸酯、2-丙基-2-金剛烷基甲基丙烯酸酯、2-甲氧基丁基-2-金剛烷基甲基丙烯酸酯、8-甲基-8-三環癸基甲基丙烯酸酯、8-乙基-8-三環癸基甲基丙烯酸酯、5-甲基丙烯醯基氧基-6-羥基降冰片烯-2-羧酸-
6-內酯、及2,2,3,3,4,4,4-七氟丁基甲基丙烯酸酯等。
丙烯醯胺化合物,可舉例如丙烯醯胺、N-甲基丙烯醯胺、N-乙基丙烯醯胺、N-苄基丙烯醯胺、N-苯基丙烯醯胺、及N,N-二甲基丙烯醯胺等。
聚甲基丙烯酸醯胺化合物的原料單體,可舉例如甲基丙烯基醯胺、N-甲基甲基丙烯基醯胺、N-乙基甲基丙烯基醯胺、N-苄基甲基丙烯基醯胺、N-苯基甲基丙烯基醯胺、及N,N-二甲基甲基丙烯基醯胺等。
聚乙烯基化合物的原料單體,可舉例如乙烯基醚、甲基乙烯基醚、苄基乙烯基醚、2-羥基乙基乙烯基醚、苯基乙烯基醚、及丙基乙烯基醚等。
聚苯乙烯化合物的原料單體,可舉例如苯乙烯、甲基苯乙烯、氯苯乙烯、溴苯乙烯、及羥基苯乙烯等。
聚馬來醯亞胺化合物的原料單體,可舉例如馬來醯亞胺、N-甲基馬來醯亞胺、N-苯基馬來醯亞胺、及N-環己基馬來醯亞胺等。
此等聚合物的製造,可藉由在有機溶劑中溶解加成聚合性單體及因應必要添加的鏈移動劑(相對單體之質量在10%以下)後、添加聚合起始劑進行聚合反應,之後,添加聚合停止劑而製造。聚合起始劑的添加量,相對單體之質量為1乃至10%,聚合停止劑的添加量為0.01乃至0.2質量%。作為使用的有機溶劑,可舉例如丙二醇單甲基醚、丙二醇單丙基醚、乳酸乙酯、環己酮、甲基乙基酮、及二甲基甲醯胺等,鏈移動劑,可舉例如十二烷硫醇及十
二烷基硫醇等,聚合起始劑,可舉例如偶氮雙異丁腈及偶氮雙環己烷甲腈等,接著、聚合停止劑,可舉例如4-甲氧基酚等。反應溫度為30乃至100℃、反應時間為由1乃至48小時中適宜選擇。
本發明的阻劑底層膜形成組成物可含有交聯劑成分。該交聯劑,可舉例如三聚氰胺系、取代尿素系、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,為甲氧基甲基化甘脲、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、甲氧基甲基化尿素、丁氧基甲基化尿素、甲氧基甲基化硫基尿素、或甲氧基甲基化硫基尿素等之化合物。又,亦可使用此等之化合物的縮合體。
又,作為上述交聯劑,可使用耐熱性高的交聯劑。作為耐熱性高的交聯劑,宜使用含有分子內具有芳香族環(例如苯環、萘環)之交聯形成取代基的化合物。
此化合物可舉例如具有下述式(4)之部分構造的化合物、或具有下述式(5)之重複單位的聚合物或寡聚物。
式(4)中,R9及R10各自為氫原子、碳原子數1乃至10之烷基、或碳原子數6乃至20之芳基、n6為1乃至4之整數,n7為1乃至(5-n6)之整數,(n6+n7)為2乃至5之整數。
式(5)中,R11為氫原子或碳原子數1乃至10之烷
基,R12為碳原子數1乃至10之烷基,n8為1乃至4之整數,n9為0乃至(4-n8),(n8+n9)為1乃至4之整數。寡聚物及聚合物可在重複單位構造的數為2乃至100、或2乃至50之範圍使用。
此等之烷基及芳基可舉例如上述烷基及芳基。
式(4)、式(5)之化合物、聚合物、寡聚物如下例示。
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。例如上述交聯劑中,可使用式(4-21)之化合物(旭有機材工業(股)、商品名TM-BIP-A)、式(4-22)之化合物(本州化學工業(股)、商品名TMOM-BP)。
交聯劑的添加量雖因使用的塗佈溶劑、使用的底層基板、要求的溶液黏度、要求的膜形狀等而變動,相對全固形分為0.001乃至80質量%、較佳為0.01乃至50質量%、進而較佳為0.05乃至40質量%。此等交聯劑雖亦有因自我縮合產生交聯反應之情形,但本發明的上述聚合物中
存在交聯性取代基之場合,可與彼等之交聯性取代基產生交聯反應。
在本發明作為促進上述交聯反應用的觸媒,可搭配p-甲苯磺酸、三氟甲烷磺酸、吡啶鎓p-甲苯磺酸、水楊酸、磺水楊酸、檸檬酸、安息香酸、羥基安息香酸、萘羧酸等之酸性化合物或/及2,4,4,6-四溴環己二烯酮、安息香對甲苯磺酸酯、2-硝基苄基對甲苯磺酸酯、其他有機磺酸烷基酯等之熱酸產生劑。搭配量相對全固形分為0.0001乃至20質量%、較佳為0.0005乃至10質量%、較佳為0.01乃至3質量%。
本發明的微影術用塗佈型底層膜形成組成物,為了使與在微影術步驟,上層所被覆的光阻劑之酸性度一致,可添加光酸產生劑。較佳光酸產生劑,例如雙(4-t-丁基苯基)錪三氟甲烷磺酸酯、三苯基鋶三氟甲烷磺酸酯等之鎓鹽系光酸產生劑類、苯基-雙(三氯甲基)-s-三嗪等之含鹵素化合物系光酸產生劑類、安息香對甲苯磺酸酯、N-羥基琥珀醯亞胺三氟甲烷磺酸酯等之磺酸系光酸產生劑類等。上述光酸產生劑相對全固形分為0.2乃至10質量%、較佳為0.4乃至5質量%。
本發明的微影術用阻劑底層膜材料中,除上述以外,因應必要可更添加吸光劑、流變學調整劑、接著輔助劑、界面活性劑等。
更而吸光劑,可舉例如「工業用色素之技術與市場」(CMC出版)或「染料便覧」(有機合成化學協會編)記
載之市售吸光劑、例如宜使用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.Disperse Orangel,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,通常,相對微影術用阻劑底層膜材料之全固形分為10質量%以下、較佳為5質量%以下的比例搭配。
流變學調整劑,主係以提升阻劑底層膜形成組成物的流動性、尤其在烘烤步驟中、阻劑底層膜的膜厚均一性的提升或提高對孔洞內部之阻劑底層膜形成組成物的充填性為目的而添加。具體例,可舉例如二甲基苯二甲酸酯、二乙基苯二甲酸酯、二異丁基苯二甲酸酯、二己基苯二甲酸酯、丁基異癸基苯二甲酸酯等之苯二甲酸衍生物、二正丁基己二酸酯、二異丁基己二酸酯、二異辛基己二酸酯、辛基癸基己二酸酯等之己二酸衍生物、二正丁基蘋果酸酯、二乙基蘋果酸酯、二壬基蘋果酸酯等之馬來酸衍生物、甲基油酸酯、丁基油酸酯、四氫糠基油酸酯等之油酸衍生物、或正丁基硬脂酸酯、甘油基硬脂酸酯等之硬脂酸衍生
物。此等之流變學調整劑,相對微影術用阻劑底層膜材料之全固形分,通常以未達30質量%之比例搭配。
接著輔助劑,主要以提升基板或阻劑與阻劑底層膜形成組成物的密著性、尤其顯影中阻劑不剝離的目的添加。具體例,可舉例如三甲基氯矽烷、二甲基乙烯基氯矽烷、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、二甲基乙烯基乙氧基矽烷、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、乙烯基三氯矽烷、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、苯並三唑、苯咪唑、吲唑、咪唑、2-巰基苯咪唑、2-巰基苯並噻唑、2-巰基苯並噁唑、脲唑、硫基尿嘧啶、巰基咪唑、巰基嘧啶等之雜環式化合物、或1,1-二甲基脲、1,3-二甲基脲等之尿素、或硫基尿素化合物。此等之接著輔助劑,相對微影術用阻劑底層膜材料之全固形分通常為未達5質量%、較佳為未達2質量%之比例搭配。
在本發明的微影術用阻劑底層膜材料,為了在不產生針孔或變形等、進而提升對表面不均之塗佈性,可搭配界面活性劑。界面活性劑,可舉例如聚氧化乙烯月桂基醚、聚氧化乙烯硬脂醯基醚、聚氧化乙烯十六基醚、聚氧化乙烯油基醚等之聚氧化乙烯烷基醚類、聚氧化乙烯辛基酚
醚、聚氧化乙烯壬基酚醚等之聚氧化乙烯烷基芳基醚類、聚氧化乙烯‧聚氧化丙烯嵌段共聚物類、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、聚氧化乙烯山梨糖醇酐單月桂酸酯、聚氧化乙烯山梨糖醇酐單棕櫚酸酯、聚氧化乙烯山梨糖醇酐單硬脂酸酯、聚氧化乙烯山梨糖醇酐三油酸酯、聚氧化乙烯山梨糖醇酐三硬脂酸酯等之聚氧化乙烯山梨糖醇酐脂肪酸酯類等之非離子系界面活性劑、F-Top EF301、EF303、EF352((股)Thochem Products.製、商品名)、MEGAFACEF171、F173、R-30(大日本油墨(股)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。此等之界面活性劑的搭配量,相對本發明的微影術用阻劑底層膜材料之全固形分,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添加、或以2種以上的組合添加。
在本發明,作為溶解上述聚合物及交聯劑成分、交聯觸媒等之溶劑,可使用乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丁基醚、乙二醇單異丙基醚、乙二醇甲基醚乙酸酯、乙二醇乙基醚乙酸酯、甲基溶纖劑乙酸酯、乙基
溶纖劑乙酸酯、二乙二醇、二乙二醇單甲基醚、二乙二醇單乙基醚、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇單乙基醚乙酸酯、丙二醇、丙二醇單甲基醚、丙二醇單丁基醚、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚、丙二醇單乙基醚乙酸酯、丙二醇丙基醚乙酸酯、二丙二醇單甲基醚、二丙二醇單乙基醚、三乙二醇二甲基醚、甲苯、二甲苯、苯乙烯、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、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁烷酸甲酯、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、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯、1-辛醇、乙二醇、己二醇、三亞甲基二醇、1-甲氧基-2-丁醇、環己醇、二丙酮醇、糠基醇、四氫糠基醇、苄基醇、1,3-丁烷二醇、1,4-丁烷二醇、2,3-丁烷二醇、γ-丁基內酯、丙酮、甲基異丙基酮、二乙基酮、甲基異丁基酮、甲基正丁基酮、乙酸異丙基酮、乙酸正丙酯、乙酸異丁酯、甲醇、乙醇、異丙醇、tert-丁醇、烯丙基醇、正丙醇、2-甲基-2-丁醇、異丁醇、正丁醇、2-甲基-1-丁醇、1-戊醇、2-甲基-1-戊醇、2-乙基己醇、異丙基醚、1,4-二噁烷、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑啉酮、二甲基亞碸、N-環己基-2-吡咯烷酮等。此等之有機溶劑可單獨、或2種以上組合使用。
進而可混合丙二醇單丁基醚、丙二醇單丁基醚乙酸酯
等之高沸點溶劑使用。此等之溶劑中,丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、丙二醇單丁基醚、乳酸乙酯、乳酸丁酯、及環己酮等對平坦性的提升觀點為佳。
本發明可使用的阻劑為光阻劑或電子線阻劑。
作為本發明中微影術用阻劑底層膜的上部所塗佈的光阻劑,可使用負型、或正型,有由酚醛清漆樹脂與1,2-二疊氮基萘醌磺酸酯所成的正型光阻劑、由具有因酸分解而使鹼溶解速度上昇的基之黏著劑與光酸產生劑所成的化學增幅型光阻劑、由鹼可溶性黏著劑與因酸分解而使光阻劑的鹼溶解速度上昇的低分子化合物與光酸產生劑所成的化學增幅型光阻劑、具有因酸分解而使鹼溶解速度上昇的基之黏著劑與因酸分解而使光阻劑的鹼溶解速度上昇的低分子化合物與光酸產生劑所成的化學增幅型光阻劑、骨架具有Si原子的光阻劑等,例如Rohm and Haas公司製、商品名APEX-E。
又本發明中微影術用阻劑底層膜的上部所塗佈的電子線阻劑,可舉例如主鏈含有Si-Si鍵結、末端含有芳香族環之樹脂與經電子線照射而產生酸的酸產生劑所構成的組成物、或羥基以含N-羧基胺的有機基所取代的聚(p-羥基苯乙烯)與經電子線照射而產生酸的酸產生劑所構成的組成物等。在後者之電子線阻劑組成物,因電子線照射由酸產生劑所生成的酸與聚合物側鏈的N-羧基胺氧基反應,聚合物側鏈分解為羥基,顯示鹼可溶性,溶解於鹼顯影液,形成阻劑圖型。該經電子線照射而產生酸的酸產生劑
可舉例為1,1-雙(p-氯苯基)-2,2,2-三氯乙烷、1,1-雙(p-甲氧基苯基)-2,2,2-三氯乙烷、1,1-雙(p-氯苯基)-2,2-二氯乙烷、2-氯-6-(三氯甲基)吡啶等之鹵素化有機化合物、三苯基硫鎓鹽、二苯基錪鹽等之鎓鹽、硝基苄基對甲苯磺酸酯、二硝基苄基對甲苯磺酸酯等之磺酸酯。
作為具有使用本發明的微影術用阻劑底層膜材料形成的阻劑底層膜之阻劑的顯影液,可使用氫氧化鈉、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、四甲基氫氧化銨、四乙基氫氧化銨、膽鹼等之第4級銨鹽、吡咯、哌啶等之環狀胺類等之鹼類的水溶液。進而、在上述鹼類的水溶液亦可適當添加異丙基醇等之醇類、非離子系等之界面活性劑來使用。此等之中較佳顯影液為第四級銨鹽、進而較佳為四甲基氫氧化銨及膽鹼。
接著說明本發明的阻劑圖型形成法,係在精密積體電路元件之製造使用的基板(例如矽/二氧化矽被覆、玻璃基板、ITO基板等之透明基板)上,以旋轉器、塗佈器等之適當的塗佈方法塗佈阻劑底層膜形成組成物後、烘烤使硬化,製成塗佈型底層膜。在此、阻劑底層膜的膜厚以0.01乃至3.0μm為較佳。又塗佈後烘烤條件為80乃至350℃、0.5乃至120分鐘。之後在阻劑底層膜上直接、或因應必要使1層乃至數層的塗膜材料於塗佈型底層膜上成
膜後、塗佈阻劑,通過特定遮罩,進行光或電子線之照射,並進行顯影、洗滌、乾燥,可得到良好的阻劑圖型。因應必要亦可進行光或電子線之照射後加熱(PEB:Post Exposure Bake)。接著、將阻劑在前述步驟被顯影除去部分之阻劑底層膜以乾蝕刻除去,可使期望圖型形成於基板上。
在上述光阻劑的曝光光為近紫外線、遠紫外線、或極端紫外線(例如EUV、波長13.5nm)等之化學線,例如可使用248nm(KrF雷射光)、193nm(ArF雷射光)、157nm(F2雷射光)等之波長的光。光照射為可由光酸產生劑產生酸之方法即可,則無特別限制而可使用,曝光量為1乃至2000mJ/cm2、或10乃至1500mJ/cm2、或50乃至1000mJ/cm2。
又電子線阻劑的電子線照射,例如可使用電子線照射裝置進行照射。
在本發明,經在半導體基板以阻劑底層膜形成組成物形成該阻劑底層膜的步驟、於其上形成阻劑膜之步驟、藉由光或電子線照射與顯影形成阻劑圖型的步驟、藉由阻劑圖型蝕刻該阻劑底層膜的步驟、及藉由經圖型化的阻劑底層膜加工半導體基板之步驟,而可製造半導體裝置。
今後、伴隨阻劑圖型之微細化進展,產生解像度之問題或阻劑圖型在顯影後倒塌之問題,期望阻劑的薄膜化。因此,在基板加工難以得到充分的阻劑圖型膜厚、變得需要不僅阻劑圖型、需要使在阻劑與加工之半導體基板間作
成的阻劑底層膜具備作為基板加工時的遮罩機能之製程。如此之製程用的阻劑底層膜與以往高蝕刻速度性阻劑底層膜相異,要求具有與阻劑接近的乾蝕刻速度之選擇比的微影術用阻劑底層膜、具有比阻劑小的乾蝕刻速度之選擇比的微影術用阻劑底層膜或具有比半導體基板小的乾蝕刻速度之選擇比的微影術用阻劑底層膜。又,如此之阻劑底層膜亦可賦予防反射能力,可兼具以往防反射膜的機能。
一方面、為了得到微細的阻劑圖型,在阻劑底層膜乾蝕刻時使阻劑圖型與阻劑底層膜比阻劑顯影時的圖型寬更細的製程亦開始使用。如此之製程用的阻劑底層膜與以往高蝕刻速度性防反射膜相異,要求具有與阻劑接近的乾蝕刻速度之選擇比之阻劑底層膜。又,如此之阻劑底層膜,亦可賦予防反射能力、可兼具以往防反射膜的機能。
在本發明基板上,可使本發明的阻劑底層膜成膜後、在阻劑底層膜上直接、或因應必要將1層乃至數層的塗膜材料於阻劑底層膜上成膜後、塗佈阻劑。藉由此即使阻劑的圖型寬變窄、為了防止圖型倒塌而薄薄被覆阻劑之場合,藉由選擇適當蝕刻氣體,可進行基板之加工。
亦即,經由在半導體基板以阻劑底層膜形成組成物形成該阻劑底層膜的步驟、於其上以含矽成分等之塗膜材料形成硬遮罩或以蒸鍍形成硬遮罩(例如氮化氧化矽)之步驟、再於其上形成阻劑膜之步驟、經光或電子線之照射與顯影形成阻劑圖型之步驟、藉由阻劑圖型將硬遮罩以鹵素系氣體蝕刻之步驟、以經圖型化的硬遮罩將該阻劑底層膜
以氧系氣體或氫系氣體蝕刻之步驟、及藉由經圖型化的阻劑底層膜以鹵素系氣體加工半導體基板之步驟可製造半導體裝置。
本發明的微影術用阻劑底層膜形成組成物,考量作為防反射膜之效果的場合,因光吸收部位被包入骨架,加熱乾燥時無至光阻劑中的擴散物,又,因光吸收部位具有夠大的吸光性能,防止反射光效果高。
在本發明的微影術用阻劑底層膜形成組成物,為熱安定性高、可防止燒成時因分解物造成上層膜之污染,又,在燒成步驟之溫度裕度可使具有餘裕者。
進而、本發明的微影術用阻劑底層膜材料,因製程條件,可用作為具有防止光之反射之機能、進而防止基板與光阻劑之相互作用或防止光阻劑使用的材料或對光阻劑曝光時生成物質對基板之負面影響的機能之膜。
又,根據本發明,與上述阻劑底層膜不同用途,可提供不使用金屬氧化物、單獨達成高耐熱性、高透明性、高折射率、高溶解性之含三苯基胺環聚合物及含咔唑環聚合物。
亦即,可得到含有含上述式(1)所示之單位構造之聚合物(例如苯基萘基胺酚醛清漆樹脂)的高折射率膜形成組成物。接著塗佈上述高折射率膜形成組成物可得到高折射率膜,可得到含彼等之高折射率膜的電子裝置。該用途使用的聚合物的重量平均分子量為1000乃至2000000之高分支聚合物或線性聚合物。
為了得到高折射率膜之高折射率膜形成組成物,為含有聚合物及溶劑,固形分濃度在不影響保存安定性範圍,則不特別限定,因應目的膜的厚度適宜設定即可。具體上,由溶解性及保存安定性的觀點,固形分濃度以0.1乃至50質量%為佳、更佳為0.1乃至20質量%。溶劑可舉例如上述溶劑。
上述固形分中,上述聚合物(例如苯基萘基胺酚醛清漆樹脂)可以1乃至100質量%、或1乃至99.9質量%、或50乃至99.9質量%之比例含有。在不損及本發明的效果下,可含有聚合物及溶劑以外的其他成分、例如上述平坦劑、界面活性劑、交聯劑等。
藉由為本發明的聚合物骨架,可維持高耐熱性、高透明性,即使在使用目前為止被認為有損害耐熱性及透明性之虞的單體單位的場合,僅將聚合物骨架變更為本發明的部分構造而可控制物性。
進而,雖然為高分子量之化合物,因溶解在溶劑時為低黏度,操作性優異。
接著,因不含金屬氧化物,且聚合物單獨可表現高折射率,即使經蝕刻或灰化等之乾製程的場合,蝕刻速度成為一定,可得到均勻膜厚的被膜,製作裝置時的製程裕度擴大。
又,本發明的含三苯基胺環聚合物及含咔唑環聚合物,藉由變更合成時的起始原料之單體種類,可控制諸物性。
又,本發明的含苯基萘基胺之聚合物可用作為高耐熱性絕緣材料。
使用具有以上般高耐熱性、高透明性、高折射率、高溶解性、及低體積收縮等之特性的本發明的含苯基萘基胺之聚合物製作的膜,可利用在製作液晶顯示器、有機電致發光(EL)顯示器、光半導體(LED)元件、固體攝影元件、有機薄膜太陽電池、色素增感太陽電池、有機薄膜電晶體(TFT)等之電子裝置時的一構件。
本發明亦關於利用於彼等用途的前述聚合物與其他聚合物(熱可塑性樹脂或熱可塑性樹脂組成物)之組成物。
聚合物的具體例,無特別限制,可舉例如聚乙烯樹脂、聚丙烯樹脂、聚苯乙烯樹脂、丙烯腈/丁二烯/苯乙烯樹脂(ABS)、聚碳酸酯樹脂、聚乙烯對苯二甲酸酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、(甲基)丙烯酸樹脂、聚酯樹脂(包含聚乙烯對苯二甲酸酯)、聚降冰片烯樹脂、聚乳酸樹脂、聚胺基甲酸酯樹脂、聚醚樹脂、聚醚碸樹脂、聚醚酮樹脂、聚硫基醚樹脂、酚樹脂、尿素樹脂、三聚氰胺樹脂、不飽和聚酯樹脂、環氧樹脂等。該樹脂,相對前述聚合物100質量份,以在1乃至10,000質量份的範圍使用為佳、更佳為1乃至1,000質量份的範圍。
例如為與(甲基)丙烯酸樹脂之組成物的場合,可藉由(甲基)丙烯酸酯化合物與前述聚合物混合,使該(甲基)丙烯酸酯化合物聚合而得。
(甲基)丙烯酸酯化合物的例,可舉例如甲基(甲
基)丙烯酸酯、乙基(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、1,4-丁烷二醇二(甲基)丙烯酸酯、1,6-己烷二醇二(甲基)丙烯酸酯、新戊基二醇二(甲基)丙烯酸酯、三羥甲基丙烷三氧基乙基(甲基)丙烯酸酯、三環癸烷二甲醇二(甲基)丙烯酸酯、三環癸基二(甲基)丙烯酸酯、三羥甲基丙烷三氧基丙基(甲基)丙烯酸酯、參-2-羥基乙基異氰脲酸酯三(甲基)丙烯酸酯、參-2-羥基乙基異氰脲酸酯二(甲基)丙烯酸酯、1,9-壬烷二醇二(甲基)丙烯酸酯、季戊四醇二(甲基)丙烯酸酯、甘油甲基丙烯酸酯丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三羥甲基丙烷三甲基丙烯酸酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸乙烯酯、環氧(甲基)丙烯酸酯、聚酯(甲基)丙烯酸酯及胺基甲酸酯(甲基)丙烯酸酯等。
此等之(甲基)丙烯酸酯化合物的聚合,可藉由在光自由基起始劑或熱自由基起始劑的存在下、光照射或加熱進行。
光自由基聚合起始劑,例如苯乙酮類、二苯甲酮類、米氏的苯甲醯基苯甲酸酯、醯胺肟酯、四甲基秋蘭姆單硫化物及噻噸酮類等。
尤以光分裂型之光自由基聚合起始劑為佳。光分裂型之光自由基聚合起始劑,記載於最新UV硬化技術(159
頁、(股)技術情報協會、1991年發行)。
市售光自由基聚合起始劑,可舉例如Ciba Japan(股)製 商品名:IRGACURE 184、369、651、500、819、907、784、2959、CGI1700、CGI1750、CGI1850、CG24-61、AROCUR 1116、1173、BASF公司製 商品名:ucirin TPO、UCB公司製 商品名:Ubecryl P36、Fratelli Lamberti公司製 商品名:Esacure KIP150、KIP65LT、KIP100F、KT37、KT55、KTO46、KIP75/B等。
光聚合起始劑,相對於(甲基)丙烯酸酯化合物100質量份,以在0.1乃至15質量份的範圍使用為佳、更佳為1乃至10質量份的範圍。
聚合時使用的溶劑,可使用前述膜形成用組成物中記載的溶劑。
在100mL四口燒瓶中,加入N-苯基-1-萘基胺(8.00g、0.036mol、東京化成工業(股)製)、苯甲醛(3.87g、0.036mol、東京化成工業(股)製)、對甲苯磺酸一水合物(0.727g、0.0036mol、關東化學(股)製),加入甲苯(37.92g、關東化學(股)製)並攪拌,升溫至110℃使溶解,並開始聚合。12小時後放冷至60℃後,在
甲醇(400g、關東化學(股)製)中再沈澱。過濾得到的沈澱物,以減壓乾燥機在50℃、10小時、進而120℃、24小時進行乾燥,得到目的聚合物(式(3-13))、以下簡稱pNPNA-BA)8.5g。
pNPNA-BA之GPC的聚苯乙烯換算所測定的重量平均分子量Mw為11000、多分散度Mw/Mn為7.3。接著、pNPNA-BA的NMR圖譜如圖1所示。
在100mL四口燒瓶中,加入N-苯基-1-萘基胺(10.00g、0.046mol、東京化成工業(股)製)、1-萘並醛(7.12g、0.046mol、東京化成工業(股)製)、對甲苯磺酸一水合物(0.908g、0.0046mol、關東化學(股)製),加入1,4-二噁烷(21.03g、關東化學(股)製)並攪拌,升溫至110℃使溶解,並開始聚合。12小時後放冷至室溫後、在甲醇(400g、關東化學(股)製)中再沈澱。過濾得到的沈澱物,以減壓乾燥機在50℃、10小時、進而120℃、24小時進行乾燥,得到目的聚合物(式(3-14))、以下簡稱pNPNA-NA)11.6g。
pNPNA-NA之GPC的聚苯乙烯換算所測定的重量平均分子量Mw為1400、多分散度Mw/Mn為1.62。接著、pNPNA-NA的NMR圖譜如圖2所示。
在100mL四口燒瓶中,加入N-苯基-1-萘基胺(8.00g、0.036mol、東京化成工業(股)製)、9-蒽羧基醛(7.52g、0.036mol、東京化成工業(股)製)、對甲苯磺酸一水合物(0.727g、0.0036mol、關東化學(股)製),加入甲苯(37.92g、關東化學(股)製)並攪拌,升溫至110℃使溶解,並開始聚合。12小時後放冷至60℃後,在甲醇(400g、關東化學(股)製)中再沈澱。過濾得到的沈澱物,以減壓乾燥機在50℃、10小時、進而120℃、24小時進行乾燥,得到目的聚合物(式(3-15)、以下簡稱pNPNA-AA)8.5g。
pNPNA-AA之GPC的聚苯乙烯換算所測定的重量平均分子量Mw為1400、多分散度Mw/Mn為1.63。接著、pNPNA-AA的NMR圖譜如圖3所示。
在100mL四口燒瓶中,加入N-苯基-1-萘基胺(8.00g、0.036mol、東京化成工業(股)製)、1-芘羧基醛(8.39g、0.036mol、東京化成工業(股)製)、對甲苯磺酸一水合物(0.727g、0.0036mol、關東化學(股)製),加入1,4-二噁烷(21.03g、關東化學(股)製)並攪拌,升溫至110℃使溶解,並開始聚合。12小時後放冷至室溫後、在甲醇(400g、關東化學(股)製)中再沈澱。過濾得到的沈澱物,以減壓乾燥機在50℃、10小時、進而120℃、24小時進行乾燥,得到目的聚合物(式
(3-16))、以下簡稱pNPNA-Py)8.4g。
pNPNA-Py之GPC的聚苯乙烯換算所測定的重量平均分子量Mw為1000、多分散度Mw/Mn為1.62。接著、pNPNA-Py的NMR圖譜如圖4所示。
在100mL四口燒瓶中,加入N-苯基-1-萘基胺(6.56g、0.030mol、東京化成工業(股)製)、咔唑(5.00g、0.030mol、東京化成工業(股)製)、1-萘並醛(9.35g、0.060mol、東京化成工業(股)製)、對甲苯磺酸一水合物(1.19g、0.0060mol、關東化學(股)製),加入1,4-二噁烷(51.57g、關東化學(股)製)並攪拌,升溫至110℃使溶解,並開始聚合。12小時後放冷至室溫後、在甲醇(400g、關東化學(股)製)中再沈澱。過濾得到的沈澱物,以減壓乾燥機在50℃、10小時、進而120℃、24小時進行乾燥,得到目的聚合物(式(3-19))、以下簡稱pNPNA-Cz-NA)8.4g。
pNPNA-Cz-NA之GPC的聚苯乙烯換算所測定的重量平均分子量Mw為1400、多分散度Mw/Mn為1.37。
在100mL四口燒瓶中,加入N-苯基-1-萘基胺(6.56g、0.030mol、東京化成工業(股)製)、咔唑(5.00g、0.030mol、東京化成工業(股)製)、1-萘並醛
(4.67g、0.030mol、東京化成工業(股)製)、4-甲基苯甲醛(3.60g、0.030mol、東京化成工業(股)製)、對甲苯磺酸一水合物(1.19g、0.0060mol、關東化學(股)製),加入1,4-二噁烷(49.02g、關東化學(股)製)並攪拌,升溫至110℃使溶解,並開始聚合。12小時後放冷至室溫後、在甲醇(400g、關東化學(股)製)中再沈澱。過濾得到的沈澱物,以減壓乾燥機在50℃、10小時、進而120℃、24小時進行乾燥,得到目的聚合物(式(3-21))、以下簡稱pNPNA-Cz-NA-MBA)8.4g。
pNPNA-Cz-NA-MBA之GPC的聚苯乙烯換算所測定的重量平均分子量Mw為1400、多分散度Mw/Mn為1.37。
在100mL四口燒瓶中,加入N-苯基-1-萘基胺(10.43g、0.048mol、東京化成工業(股)製)、三苯基胺(5.00g、0.020mol、東京化成工業(股)製)、1-芘羧基醛(15.63g、0.068mol、東京化成工業(股)製)、對甲苯磺酸一水合物(1.35g、0.0068mol、關東化學(股)製),加入1,4-二噁烷(75.62g、關東化學(股)製)並攪拌,升溫至110℃使溶解,並開始聚合。12小時後放冷至室溫後、在甲醇(400g、關東化學(股)製)中再沈澱。過濾得到的沈澱物,以減壓乾燥機在50℃、10小時、進而120℃、24小時進行乾燥,得到目的聚合物(式
(3-20))、以下簡稱pNPA-TPA-Py)8.4g。
pNPNA-TPA-Py之GPC的聚苯乙烯換算所測定的重量平均分子量Mw為1400、多分散度Mw/Mn為1.39。
在合成例1得到的樹脂20g,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g、作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程用的阻劑底層膜形成組成物的溶液。
在合成例2得到的樹脂20g中,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g、作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,並溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程用的阻劑底層膜形成組成物的溶液。
在合成例3得到的樹脂20g中,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g、作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程用的阻劑底層膜形成組成物的溶液。
合成例4得到的樹脂20g中,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g、作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程用的阻劑底層膜形成組成物的溶液。
合成例5得到的樹脂20g中,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g、作為界面活性劑的
MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程用的阻劑底層膜形成組成物的溶液。
合成例6得到的樹脂20g中,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程用的阻劑底層膜形成組成物的溶液。
合成例7得到的樹脂20g中,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g、作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微
影術製程用的阻劑底層膜形成組成物的溶液。
在市售酚酚醛清漆樹脂(使用酚與甲醛得到的酚醛清漆樹脂、重量平均分子量為Mw2000)20g中,混合作為交聯劑的TMOM-BP(本州化學工業(股)製、商品名)4.0g、作為觸媒的吡啶鎓對甲苯磺酸酯0.60g、作為界面活性劑的MEGAFACER-30(大日本油墨化學(股)製、商品名)0.06g,溶解於環己酮283.59g作成溶液。之後,使用孔徑0.10μm之聚乙烯製微過濾器進行過濾,再使用孔徑0.05μm之聚乙烯製微過濾器進行過濾,調製多層膜之微影術製程用的阻劑底層膜形成組成物的溶液。
將實施例1乃至7調製的阻劑底層膜溶液分別使用旋轉塗佈器在矽晶圓上塗佈。在加熱板上進行240℃、1分鐘、或400℃、2分鐘燒成,形成阻劑底層膜(膜厚0.25μm)。將此等之阻劑底層膜使用分光橢圓偏光儀,測定在波長248nm及在波長193nm之折射率(n值)及光學吸光係數(k值、亦稱衰減係數)。結果如表1所示。
將實施例1乃至7及比較例1所調製的阻劑底層膜形成組成物的溶液,分別使用旋轉塗佈器,在矽晶圓上塗佈。加熱板上進行400℃、2分鐘燒成,形成阻劑底層膜(膜厚0.25μm)。將該阻劑底層膜浸漬於阻劑使用之溶劑,例如乳酸乙酯、以及丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、環己酮,確認於該溶劑為不溶。
乾蝕刻速度的測定使用的刻蝕機及蝕刻氣體為使用以下者。
ES401(Nippon Scientific Co.,Ltd.製):CF4
將實施例1乃至7及比較例1所調製的阻劑底層膜形成組成物的溶液,分別使用旋轉塗佈器,在矽晶圓上塗佈。加熱板上進行240℃ 1分鐘、或400℃ 2分鐘燒成,形成阻劑底層膜(膜厚0.25μm)。蝕刻氣體使用CF4氣體測定乾蝕刻速度。
塗佈比較例1所調製的阻劑底層膜形成組成物,進行在240℃進行1分鐘燒成而得到的樹脂膜(膜厚0.25μm)之蝕刻速度為1.00時的實施例1乃至7及比較例1之阻劑底層膜的乾蝕刻速度的比較。結果如表2所示。速度比為(阻劑底層膜)/(比較例1之樹脂膜)之乾蝕刻速度比。
各自對實施例1乃至7所得到的酚醛清漆樹脂薄膜,測定膜厚、以及波長550nm及633nm中之折射率。結果如表3所示。
如表3所示般,可知本發明的苯基萘基胺酚醛清漆樹脂,波長550nm中折射率為1.75乃至1.80、波長633nm中折射率為1.68乃至1.78,即使為樹脂單體亦為非常高折射率。
本發明的多層膜之微影術製程中使用的阻劑底層膜材料,可提供與以往高蝕刻速度性防反射膜相異,具有與光阻劑相近或比光阻劑小的乾蝕刻速度之選擇比、比半導體基板小的乾蝕刻速度之選擇比,進而亦可兼具作為防反射膜之效果之阻劑底層膜。又,可知本發明的底層膜材料具有可在上層以蒸鍍形成硬遮罩的耐熱性。
又本發明的苯基萘基胺酚醛清漆樹脂,因在可視域之透明性與耐熱性優異、具有高折射率,且對種種溶劑之溶
解性優異,可廣泛應用在液晶顯示元件的保護膜、TFT陣列平坦化膜、彩色濾光片等之保護膜、間隔件材、EL顯示器之光取出提升膜、攝影元件之光攝入提升層、LED元件中取光提升層等光學構件。
〔圖1〕合成例1所得到的聚合物的1H-NMR圖譜。
〔圖2〕合成例2所得到的聚合物的1H-NMR圖譜。
〔圖3〕合成例3所得到的聚合物的1H-NMR圖譜。
〔圖4〕合成例4所得到的聚合物的1H-NMR圖譜。
Claims (14)
- 一種聚合物,其特徵係含有下述式(1):
- 如請求項1記載之聚合物,其中,上述式(1)的R5為氫原子,R4為可經取代的苯基、萘基、蒽基、或芘基。
- 如請求項1或請求項2記載之聚合物,其中,上述式(1)的R3為氫原子或苯基。
- 如請求項1或請求項2記載之聚合物,其中,上述重複單位構造(A)中,含有Ar1與Ar2中任一者為苯環,另一者為萘環之單位構造(a1)。
- 如請求項1或請求項2記載之聚合物,其中,上述重複單位構造(A)中,含有Ar1與Ar2皆為苯環的單位構造(a2)。
- 一種聚合物,其特徵係含有請求項4記載之單位構造(a1)與請求項5記載之單位構造(a2)的共聚合物。
- 一種聚合物,其特徵係含有請求項1記載之式(1)之重複單位構造(A)與下述式(2)之單位構造(B):
- 一種聚合物,其特徵係該聚合物為含有請求項4記載之單位構造(a1)與請求項7記載之單位構造(B)之共聚合物。
- 一種微影術用阻劑底層膜形成組成物,其特徵係含有請求項1乃至請求項8中任1項記載之聚合物。
- 如請求項9記載之阻劑底層膜形成組成物,其更含有交聯劑。
- 如請求項9或請求項10記載之阻劑底層膜形成組成物,其更含有酸及/或酸產生劑。
- 一種阻劑底層膜,其特徵係藉由將請求項9或請求項10記載之阻劑底層膜形成組成物塗佈於半導體基板上並進行燒成而得到。
- 一種半導體裝置之製造方法,其特徵係包含在半導體基板上以請求項9或請求項10記載之阻劑底層膜形成組成物形成底層膜之步驟、於其上形成阻劑膜之步驟、經光或電子線之照射與顯影形成阻劑圖型之步驟、經該阻劑圖型使該底層膜進行蝕刻之步驟、及透過經圖型化的該底層膜加工半導體基板之步驟。
- 一種半導體裝置之製造方法,其特徵係包含在半導體基板以請求項9乃至請求項11之中任1項記載之阻劑底層膜形成組成物形成底層膜之步驟、於其上形成硬遮罩之步驟、再於其上形成阻劑膜之步驟、經光或電子線之照射與顯影形成阻劑圖型之步驟、經該阻劑圖型蝕刻該硬遮罩之步驟、透過經圖型化的該硬遮罩蝕刻該底層膜之步驟、及透過經圖型化的該底層膜加工半導體基板之步驟。
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US9263286B2 (en) | 2016-02-16 |
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CN103827159A (zh) | 2014-05-28 |
JPWO2013047516A1 (ja) | 2015-03-26 |
JP6066092B2 (ja) | 2017-01-25 |
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