TWI603147B - 光阻材料及圖案形成方法 - Google Patents
光阻材料及圖案形成方法 Download PDFInfo
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- TWI603147B TWI603147B TW105123506A TW105123506A TWI603147B TW I603147 B TWI603147 B TW I603147B TW 105123506 A TW105123506 A TW 105123506A TW 105123506 A TW105123506 A TW 105123506A TW I603147 B TWI603147 B TW I603147B
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- 238000000034 method Methods 0.000 title claims description 17
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- 230000008569 process Effects 0.000 title description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
- 239000000463 material Substances 0.000 claims description 67
- 229910052799 carbon Inorganic materials 0.000 claims description 49
- 229920000642 polymer Polymers 0.000 claims description 47
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 29
- 125000004122 cyclic group Chemical group 0.000 claims description 28
- 125000001033 ether group Chemical group 0.000 claims description 28
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- 125000003118 aryl group Chemical group 0.000 claims description 21
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
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- 159000000008 strontium salts Chemical class 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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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
- G03F7/004—Photosensitive materials
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/22—Esters containing nitrogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/38—Esters containing sulfur
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F224/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
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Description
本發明係關於光阻材料、及使用了該光阻材料之圖案形成方法。
伴隨LSI之高整合化與高速化,圖案規則的微細化急速進展。尤其,快閃記憶體市場的擴大與記憶容量之增大牽引著微細化。就最先進的微細化技術而言,利用ArF微影之65nm節點之器件的量產已在進行,下一世代之利用ArF浸潤微影之45nm節點之量產準備正進行中。就再下世代之32nm節點而言,組合比起水有更高折射率之液體、高折射率透鏡及高折射率光阻膜之利用超高NA透鏡所為之浸潤微影、波長13.5nm之極端紫外線(EUV)微影、ArF微影之雙重曝光(雙重圖案化微影)等為候選,已在進行研究。
電子束(EB)、X射線等波長非常短的高能射線,光阻材料使用之烴幾乎無吸收,主要係探討以烴構成之聚羥基苯乙烯系之光阻材料。
就遮罩製作用曝光裝置而言,為了提高線寬的精度,已將利用雷射束之曝光裝置替換成使用利用EB之曝光裝置。又,可藉由提高電子槍的加速電壓而更為微細化,故從10kV移到30kV,最近50kV為主流,也有人研究100kV。
在此,伴隨加速電壓之上昇,光阻膜之低感度化成為問題。加速電壓若上昇,前方散射在光阻膜內的影響減小,故電子描繪能量之對比度提高而解像度、尺寸控制性提高,但是因為電子以直接穿越光阻膜內的狀態通過,故光阻膜之感度降低。遮罩曝光機係以直描的一筆畫曝光,故光阻膜之感度降低造成生產性降低,並非理想。由於高感度化之要求,有人探討化學增幅光阻材料。
伴隨微細化的進行,因酸擴散所致圖像模糊成為問題。為了確保尺寸45nm以下之微細圖案的解像性,有人提出不只以往提出之溶解對比度之提高為重要,酸擴散之控制亦為重要(非專利文獻1)。但是化學增幅光阻材料因為酸擴散而提高感度與對比度,若欲縮短曝光後烘烤(PEB)溫度、時間而壓抑酸擴散到極限,感度與對比度會顯著降低。
感度、解像度及邊緣粗糙度處於三角取捨關係。在此,為了提高解像性,有必要壓抑酸擴散,但是若酸擴散距離縮短,感度會降低。
添加產生體積大的酸的酸產生劑而抑制酸擴散係為有效。有人提出使聚合物中含有來自作為酸產生劑之含聚合性不飽和鍵之鎓鹽的重複單元。專利文獻1
提出包含產生特定磺酸之含聚合性不飽和鍵之鋶鹽、錪鹽。專利文獻2提出磺酸直接鍵結於主鏈之鋶鹽。
也有人進行以體積大的酸產生劑以外之方法抑制酸擴散的研究。專利文獻3~8記載含有氮原子之密合性基。為了控制酸擴散,存在氮原子之電子對係為有效。但是氮原子不止防止酸擴散,有時也會抑制酸觸媒反應,於此情形,脫保護反應不進行、或即使進行其速度亦緩慢,故會發生對比度降低的問題。
[專利文獻1]日本特開2006-045311號公報
[專利文獻2]日本特開2006-178317號公報
[專利文獻3]日本特開2011-203656號公報
[專利文獻4]國際公開第2011/024953號
[專利文獻5]國際公開第2012/043102號
[專利文獻6]國際公開第2013/129342號
[專利文獻7]日本特開2012-62371號公報
[專利文獻8]日本特開2012-197382號公報
[非專利文獻1]SPIE Vol. 6520 65203L-1 (2007)
本發明有鑑於前述情事,目的為提供減少酸擴散且以比起習知光阻材料更高解像度,邊緣粗糙度(LER、LWR)小,給予良好圖案形狀之光阻材料,並提供使用該光阻材料之圖案形成方法。
本案發明人等為了獲得近年期待的高感度、高解像度及邊緣粗糙度小的光阻材料努力研究,結果發現:若將包括含有唑啶二酮(oxazolidinedione)、硫酮基唑烷酮(thioxooxazolidinone)、四氫噻唑二酮(thiazolidinedione)或硫酮基四氫噻唑烷酮(thioxothiazolidinone)結構之重複單元之聚合物當作光阻材料之基礎樹脂,尤其當作化學增幅光阻材料之基礎樹脂使用則極有效。
又,本案發明人等為了抑制酸擴散而使溶解對比度提高,將包括含有羧基之氫原子取代為酸不安定基而得之重複單元及/或苯酚性羥基之氫原子取代為酸不安定基而得之重複單元、及含有唑啶二酮(oxazolidinedione)、硫酮基唑烷酮(oxazolidinone)、四氫噻唑(thiazolidine)二酮或硫酮基四氫噻唑烷酮(thioxothiazolidinone)結構之預定之重複單元之聚合物作為光阻材料之基礎樹脂,尤其作為化學增幅光阻材料之基礎樹脂使用,藉此,獲得高感度、曝光前後之鹼溶解速度對比度非常高、抑制酸擴散成效高、有高解像性,且曝光後之
圖案形狀與邊緣粗糙度良好,尤其適合超LSI製造用或光罩之微細圖案形成用之光阻材料,尤其化學增幅光阻材料。
本發明之光阻材料,尤其是酸產生劑之分解效率可提高,故高感度、抑制酸擴散之效果高、有高解像性且邊緣粗糙度小,處理適應性優異,曝光後之圖案形狀良好。由於有該等優良特性,故實用性極高,作為超LSI用光阻材料及遮罩圖案形成材料非常有效。
亦即,本發明提供下列光阻材料及圖案形成方法。
1.一種光阻材料,包含基礎樹脂,該基礎樹脂包括含有下式(a)表示之重複單元與羧基之氫原子取代為酸不安定基而得之重複單元及/或苯酚性羥基之氫原子取代為酸不安定基而得之重複單元且重量平均分子量為1,000~500,000之範圍之聚合物;
式中,R1表示氫原子或甲基;R2及R3各自獨立地表示氫原子、或碳數1~6之直鏈狀、分支狀或環狀之烷基;X1表示單鍵;含有酯基、醚基或內酯環之碳數1~12之連結基;伸苯基;或伸萘基;X2及X3各自獨立地表示氧原子或硫原子;a表示符合0<a<1.0之正數。
2.如1.之光阻材料,其中,該羧基之氫原子取代為酸不安定基之而得之重複單元以下式(b1)表示,該苯酚性羥基之氫原子取代為酸不安定基而得之重複單元以下式(b2)表示;
式中,R4及R6各自獨立地表示氫原子或甲基;R5及R9各自獨立地表示酸不安定基;R7表示單鍵、或碳數1~6之直鏈狀或分支狀之伸烷基;R8表示氫原子、氟原子、三氟甲基、氰基、或碳數1~6之直鏈狀、分支狀或環狀之烷基、醯基、烷氧基、醯氧基或烷氧基羰基;p表示1或2;q表示0~4之整數;Y1表示單鍵;含有酯基、醚基或內酯環之碳數1~12之連結基;伸苯基;或伸萘基;Y2表示單鍵、-C(=O)-O-、或-C(=O)-NH-;b1及b2表示符合0≦b1<1.0、0≦b2<1.0、及0<b1+b2<1.0之正數。
3.如1.或2.之光阻材料,其中,該聚合物更包括含有選自羥基、羧基、內酯環、碳酸酯基、硫碳酸酯基、羰基、環狀縮醛基、醚基、酯基、磺酸酯基、氰基、醯胺基、及-O-C(=O)-G-(G為-S-或-NH-)中之密合性基之重複單元。
4.如1.至3.中任一項之光阻材料,其中,該聚合物更含有選自下式(d1)~(d3)中之至少1個重複單元;[化3]
式中,R20、R24及R28各自獨立地表示氫原子或甲基;R21表示單鍵、伸苯基、-O-RA-、或-C(=O)-Y0-RA-,Y0表示-O-或-NH-,RA表示也可以含有羰基、酯基、醚基或羥基之碳數1~6之直鏈狀、分支狀或環狀之伸烷基或碳數2~12之伸烯基、或伸苯基;R22、R23、R25、R26、R27、R29、R30及R31各自獨立地表示也可以含有羰基、酯基或醚基之碳數1~12之直鏈狀、分支狀或環狀之烷基、或碳數6~12之芳基、碳數7~20之芳烷基或巰基苯基;Z1表示單鍵、或也可以含有醚基、酯基或內酯環之碳數1~12之直鏈狀、分支狀或環狀之伸烷基、或碳數2~12之直鏈狀、分支狀或環狀之伸烯基、或碳數6~10之伸芳基;Z2表示單鍵、亞甲基、伸乙基、伸苯基、氟化之伸苯基、-O-R32-、或-C(=O)-Z3-R32-,Z3表示-O-或-NH-,R32表示也可以含有羰基、酯基、醚基或羥基之碳數1~12之直鏈狀、分支狀或環狀之、伸烷基或伸烯基、或伸苯基;M-表示非親核性相對離子;d1~d3表示符合0≦d1≦0.5、0≦d2≦0.5、0≦d3≦0.5、及0<d1+d2+d3≦0.5之正數。
5.如1.至4.中任一項之光阻材料,更含有酸產生劑及有機溶劑。
6.如5.之光阻材料,更含有鹼性化合物及/或界面活性劑。
7.一種圖案形成方法,包括以下步驟:將如1.至6.中任一項之光阻材料塗佈在基板上;
加熱處理後以高能射線曝光;及使用顯影液進行顯影。
8.如7.之圖案形成方法,其中,該高能射線係i射線、KrF準分子雷射、ArF準分子雷射、電子束、或波長3~15nm之範圍之軟X射線。
本發明之光阻材料,抑制酸擴散之效果高,有高解像性,且曝光後之圖案形狀及邊緣粗糙度為良好。因此尤其適合作為超LSI製造用或利用EB描繪所為之光罩之微細圖案形成用材料、i射線、KrF準分子雷射、ArF準分子雷射、EB或EUV曝光用之圖案形成材料。
又,本發明之光阻材料,尤其化學增幅光阻材料,不只可使用在例如半導體電路形成之微影,也可使用於遮罩電路圖案之形成、或微型機器、薄膜磁頭電路形成。
本發明之光阻材料中含有的基礎樹脂,包括含有下式(a)表示之重複單元(以下稱為重複單元a)、及羧基之氫原子取代為酸不安定基而得之重複單元及/或苯
酚性羥基之氫原子取代為酸不安定基而得之重複單元之聚合物(以下稱為基礎聚合物。)。
式中,R1表示氫原子或甲基。R2及R3各自獨立地表示氫原子、或碳數1~6之直鏈狀、分支狀或環狀之烷基。X1表示單鍵;含有酯基、醚基或內酯環之碳數1~12之連結基;伸苯基;或伸萘基。X2及X3各自獨立地表示氧原子或硫原子。a表示符合0<a<1.0之正數。
作為給予重複單元a之單體Ma可列舉下式(Ma)表示者。
式中,R1~R3及X1~X3同前述。
單體Ma,例如可利用下式(a1)表示之化合物與下式(a2)表示之化合物之醯胺化反應合成。
[化6]
式中,R1~R3及X1~X3同前述。X4表示氫原子、氯原子、溴原子等鹵素原子、或下式表示之基。
式中,R1及X1同前述。破折線代表鍵結手。
單體Ma可列舉如下但不限於此等。又,下式中,R1同前述。
[化10]
重複單元a之特徵為包括唑啶二酮(oxazolidinedione)、硫酮基唑烷酮(oxazolidinone)、四氫噻唑(thiazolidine)二酮或硫酮基四氫噻唑烷酮(thioxothiazolidinone)結構。包括氮原子及氧原子兩者的醯胺基、胺甲酸酯基抑制酸擴散之效果過高,有會抑制脫保護反應的缺點,但唑啶二酮、硫酮基唑烷酮(oxazolidinone)、四氫噻唑(thiazolidine)二酮或硫酮基四氫噻唑烷酮(thioxothiazolidinone)衍生物利用醯胺鍵鍵結於主鏈而得之重複單元a因為在氮原子周圍存在3個羰基或2個羰基與1個硫羰基,氮原子完全無鹼性,不會妨礙利用酸觸媒之脫保護反應。而利用之氮原子之孤對電子抑制酸擴散之效果高。利用3個羰基可確保密合性,利用氮原子之孤對電子可抑制酸擴散,藉此能減少圖案崩塌與邊緣粗糙度(LWR)。
就前述羧基之氫原子取代為酸不安定基而得之重複單元(以下稱為重複單元b1),宜為下式(b1)表示者較理想,就前述苯酚性羥基之氫原子取代為酸不安定基而得之重複單元(以下稱為重複單元b2)而言,式(b2)表示之者較佳。
式中,R4及R6各自獨立地表示氫原子或甲基。R5及R9各自獨立地表示酸不安定基。R7表示單鍵、或碳數1~6之直鏈狀或分支狀之伸烷基。R8表示氫原子、氟原子、三氟甲基、氰基、或碳數1~6之直鏈狀、分支狀或環狀之、烷基、醯基、烷氧基、醯氧基或烷氧基羰基。p表示1或2。q表示0~4之整數。Y1表示單鍵;含有酯基、醚基或內酯環之碳數1~12之連結基;伸苯基;或伸萘基。Y2表示單鍵、-C(=O)-O-、或-C(=O)-NH-。
作為給予重複單元b1之單體Mb1可列舉下式(Mb1)表示者。作為給予重複單元b2之單體Mb2可列舉下式(Mb2)表示者。
[化12]
式中,R4~R9、Y1、Y2、p及q同前述。
作為Y1表示之含內酯環之碳數1~12之連結基可列舉以下所示者等。
單體Mb1可列舉如下但不限於此等。又,下式中,R4及R5同前述。
[化15]
單體Mb2可列舉如下但不限於此等。又,下式中,R6及R9同前述。
[化16]
R5或R9表示之酸不安定基有各種可選擇,例如:下式(A-1)~(A-3)表示者。
[化18]
式(A-1)中,RL1為碳數4~20,較佳為4~15之3級烷基、各烷基各為碳數1~6之烷基三烷基矽基、碳數4~20之側氧基烷基、或式(A-3)表示之基。A1表示0~6之整數。
前述3級烷基可列舉第三丁基、第三戊基、1,1-二乙基丙基、1-乙基環戊基、1-丁基環戊基、1-乙基環己基、1-丁基環己基、1-乙基-2-環戊烯基、1-乙基-2-環己烯基、2-甲基-2-金剛烷基等。作為前述三烷基矽基,可列舉三甲基矽基、三乙基矽基、二甲基-第三丁基矽基等。作為前述側氧基烷基,可以列舉3-側氧基環己基、4-甲基-2-側氧基烷-4-基、5-甲基-2-側氧基四氫呋喃-5-基等。
作為式(A-1)表示之酸不安定基,可以列舉第三丁氧基羰基、第三丁氧基羰基甲基、第三戊氧基羰基、第三戊氧基羰基甲基、1,1-二乙基丙氧基羰基、1,1-二乙基丙氧基羰基甲基、1-乙基環戊氧基羰基、1-乙基環戊氧基羰基甲基、1-乙基-2-環戊烯氧基羰基、1-乙基-2-環戊烯氧基羰基甲基、1-乙氧基乙氧基羰基甲基、2-四氫哌喃氧羰基甲基、2-四氫呋喃氧基羰基甲基等。
又,作為式(A-1)表示之酸不安定基,下式(A-1)-1~(A-1)-10表示之基亦可理想地使用。
式中,RL8各自獨立地表示碳數1~10之直鏈狀、分支狀或環狀之烷基、或碳數6~20之芳基。RL9表示氫原子、或碳數1~10之直鏈狀、分支狀或環狀之烷基。RL10表示碳數2~10之直鏈狀、分支狀或環狀之烷基、或碳數6~20之芳基。A1同前述。
式(A-2)中,RL2及RL3各自獨立地表示氫原子、或碳數1~18,較佳為1~10之直鏈狀、分支狀或環狀之烷基。作為前述烷基可列舉甲基、乙基、丙基、異丙基、正丁基、第二丁基、第三丁基、環戊基、環己基、2-乙基己基、正辛基等。RL4表示也可以含有氧原子等雜原子之碳數1~18,較佳為1~10之1價烴基。作為前述1價烴基,可列舉直鏈狀、分支狀或環狀之烷基等,該等氫原子之一部分也可以取代為羥基、烷氧基、側氧基、胺基、烷胺基等。如此的取代烷基可列舉以下所示者等。
RL2與RL3、RL2與RL4、或RL3與RL4也可互相鍵結並和它們所鍵結之碳原子一起、或和碳原子與氧原子一起形成環,於此情形涉及環形成之RL2及RL3、RL2及RL4、或RL3及RL4各自獨立地表示碳數1~18,較佳為1~10之直鏈狀或分支狀之伸烷基。它們鍵結而獲得之環之碳數較佳為3~10,更佳為4~10。
式(A-2)表示之酸不安定基之中,直鏈狀或分支狀者可列舉下式(A-2)-1~(A-2)-69表示者,但不限定於此等。
[化21]
[化22]
[化23]
[化24]
式(A-2)表示之酸不安定基之中,環狀者可列舉四氫呋喃-2-基、2-甲基四氫呋喃-2-基、四氫哌喃-2-基、2-甲基四氫哌喃-2-基等。
又,酸不安定基可列舉下式(A-2a)或(A-2b)表示之基。也可利用前述酸不安定基將基礎聚合物進行分子間或分子內交聯。
式中,RL11及RL12各自獨立地表示氫原子、或碳數1~8之直鏈狀、分支狀或環狀之烷基。RL11與RL12亦可互相鍵結並和它們所鍵結之碳原子一起形成環,於此情形,RL11及RL12各自獨立地表示碳數1~8之直鏈狀或分支狀之伸烷基。RL13各自獨立地表示碳數1~10之直鏈狀、分支狀或環狀之伸烷基。B1及D1各自獨立地表示0~10之整數,較佳為0~5之整數,C1表示1~7之整數,較佳為1~3之整數。
A表示(C1+1)價之碳數1~50之脂肪族或脂環族飽和烴基、芳香族烴基、或雜環基。又,該等基之碳原子間也可以含有雜原子,或該等基之碳原子所鍵結之一部分氫原子也可取代為羥基、羧基、醯基或氟原子。就A而言,宜為直鏈狀、分支狀或環狀之伸烷基、烷基三基、烷基四基、碳數6~30之伸芳基等為較佳。B表示-CO-O-、-NHCO-O-或-NHCONH-。
式(A-2a)或(A-2b)表示之交聯型縮醛基可列舉下式(A-2)-70~(A-2)-77表示之基等。
[化26]
式(A-3)中,RL5、RL6及RL7各自獨立地表示碳數1~20之直鏈狀、分支狀或環狀之烷基或碳數2~20之直鏈狀、分支狀或環狀之烯基等1價烴基,也可以含有氧原子、硫原子、氮原子、氟原子等雜原子。又,RL5與RL6、RL5與RL7、或RL6與RL7也可以互相鍵結並和它們所鍵結之碳原子一起形成碳數3~20之脂環。
作為式(A-3)表示之3級烷基,可以列舉第三丁基、三乙基香芹基(carvyl)、1-乙基降莰基、1-甲基環己基、1-乙基環戊基、2-(2-甲基)金剛烷基、2-(2-乙基)金剛烷基、第三戊基等。
又,作為式(A-3)表示之3級烷基,也宜使用下式(A-3)-1~(A-3)-18表示之基。
式中,RL14各自獨立地表示碳數1~8之直鏈狀、分支狀或環狀之烷基、或碳數6~20之苯基等芳基。RL15及RL17各自獨立地表示氫原子、或碳數1~20之直鏈狀、分支狀或環狀之烷基。RL16表示碳數6~20之苯基等芳基。
又,酸不安定基可以列舉下式(A-3)-19或(A-3)-20表示之基。也可以利用前述酸不安定基將聚合物進行分子內或分子間交聯。
式中,RL14同前述。RL18表示碳數1~20之直鏈狀、分支狀或環狀之(E1+1)價之脂肪族烴基、或碳數6~20之2~4價之芳香族烴,也可以含有氧原子、硫原子、氮原子等雜原子。E1表示1~3之整數。
含有式(A-3)表示之酸不安定基之重複單元,例如下式(A-3)-21表示之來自包括外向體結構之(甲基)丙烯酸酯者。
[化29]
式中,R4同前述。RLc1表示碳數1~8之直鏈狀、分支狀或環狀之烷基、或也可經取代之碳數6~20之芳基。RLc2~RLc7、RLc10及RLc11各自獨立地表示氫原子、或碳數1~15之也可以含有雜原子之1價烴基。RLc8及RLc9表示氫原子。RLc2與RLc3、RLc4與RLc6、RLc4與RLc7、RLc5與RLc7、RLc5與RLc11、RLc6與RLc10、RLc8與RLc9或RLc9與RLc10也可互相鍵結並和它們所鍵結之碳原子一起形成環,於此情形涉及鍵結之基表示碳數1~15之也可以含有雜原子之2價烴基。又,RLc2與RLc11、RLc8與RLc11、或RLc4與RLc6也可鍵結於相鄰之碳者彼此直接鍵結並形成雙鍵。又,依本式也表示鏡像體。
在此,作為給予式(A-3)-21表示之重複單元之單體可列舉在日本特開2000-327633號公報記載者等。具體而言,可列舉如下但不限於此等。又,下式中,R4同前述。
[化30]
作為包括式(A-3)表示之酸不安定基之重複單元,亦可列舉下式(A-3)-22表示之來自含呋喃二基、四氫呋喃二基或氧雜降莰烷二基之(甲基)丙烯酸酯者。
式中,R4同前述。RLc12及RLc13各自獨立地表示碳數1~10之直鏈狀、分支狀或環狀之1價烴基。RLc12與RLc13也可以互相鍵結並和它們所鍵結之碳原子一起形成脂環。RLc14表示呋喃二基、四氫呋喃二基、或氧雜降莰烷二基。RLc15表示氫原子、或也可以含有雜原子之碳數1~10之直鏈狀、分支狀或環狀之1價烴基。
作為給予式(A-3)-22表示之重複單元之單體可列舉如下但不限於此等。又,下式中,R4同前述,Ac表示乙醯基,Me表示甲基。
[化33]
作為式(A-3)表示之酸不安定基亦可列舉下式(A-3)-23表示者。前述基礎聚合物含有此酸不安定基時,宜含有經該酸不安定基取代之重複單元b1較佳。
式中,RL100表示氫原子、鹵素原子、氰基、碳數1~4之烷基、碳數1~4之烷氧基、碳數2~5之醯基、碳數2~5之烷氧基羰基、或碳數6~10之芳基。k1表示1~4之整數。
作為給予含有式(A-3)-23表示之酸不安定基之重複單元之單體可列舉如下但不限於此等。又,下式中,R4同前述。
作為式(A-3)表示之酸不安定基亦可列舉下式(A-3)-24表示者。前述基礎聚合物含有此酸不安定基時,宜含經該酸不安定基取代之重複單元b1較佳。
[化36]
式中,RL101及RL102各自獨立地表示氫原子、鹵素原子、氰基、羥基、碳數1~4之烷基、碳數1~4之烷氧基、碳數2~5之醯基、碳數2~5之烷氧基羰基、或碳數6~10之芳基。R表示氫原子、或也可以含有氧原子或硫原子之碳數1~12之直鏈狀、分支狀或環狀之烷基、碳數2~12之烯基、碳數2~12之炔基、或碳數6~10之芳基。RL103、RL104、RL105及RL106表示氫原子,或RL103與RL104、RL104與RL105、或RL105與RL106亦可互相鍵結而形成苯環。k2及k3各自獨立地表示1~4之整數。
作為給予含有式(A-3)-24表示之酸不安定基之重複單元的單體,可列舉如下但不限於此等。又,下式中,R4同前述。
[化37]
[化38]
[化39]
作為式(A-3)表示之酸不安定基亦可列舉下式(A-3)-25表示者。前述基礎聚合物含有此酸不安定基時,宜含有經該酸不安定基取代之重複單元b1較佳。
式中,R同前述。RL107各自獨立地表示氫原子、或碳數1~6之直鏈狀、分支狀或環狀之烷基,k4為2以上時,RL107彼此也可以鍵結而形成碳數2~8之環。圓弧Z係連結碳原子CA與CB之2價基,表示伸乙基、伸丙基、伸丁基或伸戊基。RL108各自獨立地表示氫原子、羥基、硝基、鹵素原子、氰基、碳數1~4之烷基、碳數1~4之烷氧基、碳數2~5之醯基、碳數2~5之烷氧基羰基、或碳數6~10之芳基。Z為伸乙基或伸丙基時,RL107不為氫原子。k4及k5各自獨立地表示1~4之整數。
作為給予含有式(A-3)-25表示之酸不安定基之重複單元之單體,可列舉如下但不限於此等。又,下式中,R4同前述。
[化41]
[化42]
[化43]
[化44]
[化45]
作為式(A-3)表示之酸不安定基也可以列舉下式(A-3)-26表示者。前述基礎聚合物含有此酸不安定基時,宜含有經該酸不安定基取代之重複單元b1較佳。
[化46]
式中,R同前述。RL109及RL110各自獨立地表示氫原子、羥基、硝基、鹵素原子、氰基、碳數1~4之烷基、碳數1~4之烷氧基、碳數1~4之醯基、碳數2~5之烷氧基羰基、或碳數6~10之芳基。k6及k7各自獨立地表示1~4之整數。
作為給予含有式(A-3)-26表示之酸不安定基之重複單元之單體,可列舉如下但不限於此等。又,下式中,R4同前述。
[化47]
[化48]
作為式(A-3)表示之酸不安定基也可列舉下式(A-3)-27表示者。前述基礎聚合物含有此酸不安定基時,宜含有經該酸不安定基取代之重複單元b1較佳。
式中,R同前述。RL111及RL112各自獨立地表示氫原子、羥基、鹵素原子、氰基、碳數1~4之烷基、碳數1~4之烷氧基、碳數2~5之醯基、碳數2~5之烷氧基羰基、或碳數6~10之芳基。k8及k9各自獨立地表示1~4之整數。J表示亞甲基、伸乙基、伸乙烯基或-CH2-S-。
作為給予含有式(A-3)-27表示之酸不安定基之重複單元之單體可列舉如下但不限於此等。又,下式中,R4同前述。
[化50]
[化51]
[化52]
作為式(A-3)表示之酸不安定基也可列舉下式(A-3)-28表示者。前述基礎聚合物含有此酸不安定基時,宜含有經該酸不安定基取代之重複單元b1較佳。
式中,R同前述。RL113及RL114各自獨立地表示氫原子、羥基、鹵素原子、氰基、碳數1~4之烷基、碳數1~4之烷氧基、碳數2~5之醯基、碳數2~5之烷氧基
羰基、或碳數6~10之芳基。k10及k11各自獨立地表示1~4之整數。L表示羰基、醚基、硫醚基、-S(=O)-或-S(=O)2-。
作為給予含有式(A-3)-28表示之酸不安定基之重複單元之單體可列舉如下但不限於此等。又,下式中,R4同前述。
[化56]
[化57]
前述基礎聚合物也可以更含有包括選自羥基、羧基、內酯環、碳酸酯基、硫碳酸酯基、羰基、環狀縮醛基、醚基、酯基、磺酸酯基、氰基、醯胺基、及-O-C(=O)-G-(G為-S-或-NH-)中之密合性基之重複單元c。作為給予重複單元c之單體可列舉如下但不限於此等。
[化58]
[化59]
[化60]
[化63]
[化64]
[化65]
為含羥基之單體時,聚合時也可將羥基事先以乙氧基乙氧基等易以酸脫保護之縮醛基取代,於聚合後利用弱酸與水進行脫保護,也可事先以乙醯基、甲醯基、三甲基乙醯基等取代並於聚合後進行鹼水解。
前述基礎聚合物也可更含有下式(d1)~(d3)表示之來自鋶鹽之重複單元(以下各稱為重複單元d1~d3)。
式中,R20、R24及R28各自獨立地表示氫原子或甲基。R21表示單鍵、伸苯基、-O-RA-、或-C(=O)-Y0-RA-,Y0表示-O-或-NH-,RA表示也可以含有羰基、酯基、醚基或羥基之碳數1~6之直鏈狀、分支狀或環狀之伸烷基或碳數2~12之伸烯基、或伸苯基。R22、R23、R25、R26、R27、R29、R30及R31各自獨立地表示也可以含有羰基、酯基或醚基之碳數1~12之直鏈狀、分支狀或環狀之烷基、或碳數6~12之芳基、碳數7~20之芳烷基或巰基苯基。Z1表示單鍵、或也可以含有醚基、酯基或內酯環之碳數1~12之直鏈狀、分支狀或環狀之伸烷基、或碳數2~12之直鏈狀、分支狀或環狀之伸烯基、或碳數6~10之伸芳基。Z2表示單鍵、亞甲基、伸乙基、伸苯基、氟化之伸苯基、-O-R32-、或-C(=O)-Z3-R32-,Z3表示-O-或-NH-,R32表示也可以含有羰基、酯基、醚基或羥基之碳數1~12之直鏈狀、分支狀或環狀之伸烷基或伸烯基、或伸苯基。M-表示非親核性相對離子。
藉由使酸產生劑鍵結於聚合物主鏈可減小酸擴散,並防止酸擴散之模湖造成解像性降低。又,藉由使酸產生劑均勻分散可改善邊緣粗糙度(LER、LWR)。
作為M-表示之非親核性相對離子,可以列舉:氯化物離子、溴化物離子等鹵化物離子;三氟甲烷磺酸根、1,1,1-三氟乙烷磺酸根、九氟丁烷磺酸根等氟烷基磺酸根;甲苯磺酸根、苯磺酸根、4-氟苯磺酸根、1,2,3,4,5-五氟苯磺酸根等芳基磺酸根;甲磺酸根、丁烷磺酸根等烷基磺酸根;雙(三氟甲基磺醯基)醯亞胺、雙(全氟乙基磺醯基)醯亞胺、雙(全氟丁基磺醯基)醯亞胺等醯亞胺酸、參(三氟甲基磺醯基)甲基化物、參(全氟乙基磺醯基)甲基化物等甲基化酸。
又,作為M-表示之非親核性相對離子,可以列舉下式(K-1)表示之α位經氟取代之磺酸根、下式(K-2)表示之α及β位經氟取代之磺酸根。
式(K-1)中,R41表示氫原子、碳數1~20之直鏈狀、分支狀或環狀之烷基、碳數2~20之烯基、或碳數6~20之芳基,且也可以含有醚基、酯基、羰基、內酯環、或氟原子。
式(K-2)中,R42表示氫原子、碳數1~30之直鏈狀、分支狀或環狀之烷基、醯基、碳數2~20之烯基、碳數6~20之芳基、或芳氧基,且也可以含有醚基、酯基、羰基、或內酯環。
又,使用含有選自重複單元d1~d3中之至少1個重複單元之基礎聚合物時,可省去後述光酸產生劑之摻合。
前述基礎聚合物也可以更含有下式(e1)~(e5)表示之重複單元(以下各稱為重複單元e1~e5)。
式中,R110~R114各自獨立地表示氫原子、碳數1~30之烷基、碳原子所鍵結之一部分或全部氫原子取代為鹵素原子之碳數1~30之烷基、羥基、碳數1~30之烷氧基、碳數2~30之醯基、碳數2~30之烷氧基羰基、碳數6~10之芳基、鹵素原子、或1,1,1,3,3,3-六氟-2-丙醇基。X0表示亞甲基、醚基、或硫醚基。
前述基礎聚合物也可更含有來自苯乙烯、乙烯基萘、乙烯基蒽、乙烯基芘、亞甲基二氫茚等之重複單元f。
合成前述基礎聚合物之方法,例如將給予重複單元a~f之單體中之所望之單體於有機溶劑中,加入自由基聚合起始劑並進行加熱聚合之方法。
聚合時使用之有機溶劑可以列舉甲苯、苯、四氫呋喃、二乙醚、二烷、環己烷、環戊烷、甲乙酮、γ-丁內酯等。聚合起始劑可列舉2,2'-偶氮雙異丁腈(AIBN)、2,2'-偶氮雙(2,4-二甲基戊腈)、二甲基-2,2-偶氮雙(2-甲基丙酸酯)、過氧化苯甲醯、過氧化月桂醯等。反應溫度較佳為50~80℃,反應時間較佳為2~100小時,更佳為5~20小時。
當合成含有來自羥基苯乙烯、羥基乙烯基萘之重複單元之聚合物時,也可將羥基苯乙烯、羥基乙烯基萘替換為使用乙醯氧基苯乙烯、乙醯氧基乙烯基萘,於聚合後進行鹼水解而將乙醯氧基予以脫保護而成為羥基苯乙烯單元、羥基乙烯基萘單元。鹼水解時之鹼可使用氨水、三乙胺等。又,反應溫度較佳為-20~100℃,更佳為0~60℃,反應時間較佳為0.2~100小時,更佳為0.5~20小時。
前述基礎聚合物中,重複單元a及b之比例為0<a<1.0、0≦b1<1.0、0≦b2<1.0、0<b1+b2<1.0、0.1≦a+b1+b2≦1.0。重複單元c之比例為0≦c≦0.9,但含有重複單元c時,較佳為0<c≦0.9、0.2≦a+b1+b2+c≦1.0。於此情形更佳為0.02≦a≦0.8、0≦b1≦0.8、0≦b2≦0.8、0.1≦b1+b2≦0.8、0.1≦c≦0.88,又更佳為0.05≦a≦0.75、0≦b1≦0.7、0≦b2≦0.7、0.1≦b1+b2≦0.75、0.15≦c≦0.85,尤佳為0.07≦a≦0.7、0≦b1≦0.65、0≦b2≦0.65、0.1≦b1+b2≦0.7、
0.2≦c≦0.83。於此情形0.2≦a+b1+b2+c≦1.0,更佳為0.3≦a+b1+b2+c≦1.0,又更佳為0.4≦a+b1+b2+c≦1.0。
重複單元d1~d3之比例為0≦d1≦0.5、0≦d2≦0.5、0≦d3≦0.5、0≦d1+d2+d3≦0.5,但含有重複單元d1~d3時為0<d1+d2+d3≦0.5。於此情形,較佳為0≦d1≦0.4、0≦d2≦0.4、0≦d3≦0.4、0<d1+d2+d3≦0.4,更佳為0≦d1≦0.3、0≦d2≦0.3、0≦d3≦0.3、0<d1+d2+d3≦0.3,又更佳為0≦d1≦0.2、0≦d2≦0.2、0≦d3≦0.2、0<d1+d2+d3≦0.25。又,0.2≦a+b1+b2+c+d1+d2+d3≦1.0,但尤佳為0.4≦a+b1+b2+c+d1+d2+d3≦1.0。又,含有重複單元d1~d3時,較佳為0<d1+d2+d3≦0.5、
又,重複單元e1~e5之比例為0≦e1≦0.5、0≦e2≦0.5、0≦e3≦0.5、0≦e4≦0.5、0≦e5≦0.5、0≦e1+e2+e3+e4+e5≦0.5,但含有重複單元e1~e5時,0<e1+e2+e3+e4+e5≦0.5。於此情形,較佳為0≦e1≦0.4、0≦e2≦0.4、0≦e3≦0.4、0≦e4≦0.4、0≦e5≦0.4、0<e1+e2+e3+e4+e5≦0.4,更佳為0≦e1≦0.3、0≦e2≦0.3、0≦e3≦0.3、0≦e4≦0.3、0≦e5≦0.3、0<e1+e2+e3+e4+e5≦0.3。又,
重複單元f之比例為0≦f≦0.5,較佳為0≦f≦0.4,更佳為0≦f≦0.3。
又,a+b1+b2+c+d1+d2+d3+e1+e2+e3+e4+e5+f=1較佳。
前述基礎聚合物的重量平均分子量(Mw)為1,000~500,000,較佳為2,000~30,000。Mw若為1,000以上,光阻材料的耐熱性優異,若為500,000以下則鹼溶解性良好,圖案形成後無產生拖尾現象之虞。又,Mw係使用四氫呋喃(THF)作為溶劑之利用凝膠滲透層析(GPC)獲得之聚苯乙烯換算測定值。
前述基礎聚合物中,多成分共聚物之分子量分布(Mw/Mn)廣時,因存在低分子量、高分子量之聚合物,曝光後會在圖案上出現異物或圖案之形狀惡化。故隨著圖案規格微細化,分子量、分子量分布之影響增大,為了獲得適合微細圖案尺寸使用的光阻材料,使用之基礎聚合物之分子量分布為1.0~2.0,尤其1.0~1.5之窄分散較佳。
本發明之光阻材料中,基礎樹脂可含有前述基礎聚合物1種、含有組成比率、分子量分布、分子量等不同的2種以上之基礎聚合物掺混者、將前述基礎聚合物與不含重複單元a之聚合物予以掺混者。
本發明之光阻材料為了作為化學增幅光阻材料之作用,也可以含有酸產生劑。前述酸產生劑,例如感應活性光線或放射線而產生酸之化合物(光酸產生劑)。
前述光酸產生劑只要是因高能射線照射產酸之化合物即可任意使用。理想的光酸產生劑可列舉鋶鹽、錪鹽、磺醯基重氮甲烷、N-磺醯氧基醯亞胺、肟-O-
磺酸酯型酸產生劑等。如此的光酸產生劑之具體例可列舉日本特開2008-111103號公報之段落[0122]~[0142]記載者。
又,光酸產生劑也可理想地使用下式(1)或(2)表示者。
式(1)中,R101、R102及R103各自獨立地表示也可以含有雜原子之碳數1~20之直鏈狀、分支狀或環狀之1價烴基。又,R101、R102及R103中的任二者以上也可以互相鍵結並和它們所鍵結之硫原子一起形成環。
式(1)中,X-表示選自下式(1A)~(1D)之陰離子。
式(1A)中,Rfa表示氟原子、或也可以含有雜原子之碳數1~40之直鏈狀、分支狀或環狀之1價烴基。
式(1A)表示之陰離子宜為下式(1A')表示者較佳。
式(1A')中,R104表示氫原子或三氟甲基,較佳為三氟甲基。R105表示也可以含有雜原子之碳數1~38之直鏈狀、分支狀或環狀之1價烴基。前述雜原子宜為氧原子、氮原子、硫原子、鹵素原子等較理想,氧原子更理想。就前述1價烴基而言,考量在微細圖案形成獲得高解像性之觀點,尤其碳數6~30較佳。前述1價烴基可列舉甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、新戊基、環戊基、己基、環己基、3-環己烯基、庚基、2-乙基己基、壬基、十一基、十三基、十五基、十七基、1-金剛烷基、2-金剛烷基、1-金剛烷基甲基、降莰基、降莰基甲基、三環癸基、四環十二基、四環十二基甲基、二環己基甲基、二十基、烯丙基、苄基、二苯基甲基、四氫呋喃基、甲氧基甲基、乙氧基甲基、甲硫基甲基、乙醯胺甲基、三氟乙基、(2-甲氧基乙氧基)甲基、乙醯氧基甲基、2-羧基-1-環己基、2-側氧基丙基、4-側氧基-1-金剛烷基、3-側氧基環己基等。又,該等基之一部分氫原子也可取代為含有氧原子、硫原子、氮原子、鹵素原子等雜原子之基,或該等基之一部分碳原子間也可插入含氧原子、硫原子、
氮原子等雜原子之基,其結果也可含有羥基、氰基、羰基、醚基、酯基、磺酸酯基、碳酸酯基、內酯環、磺內酯環、羧酸酐、鹵烷基等。
關於合成含式(1A')表示之陰離子之鋶鹽詳見日本特開2007-145797號公報、日本特開2008-106045號公報、日本特開2009-7327號公報、日本特開2009-258695號公報等。又,日本特開2010-215608號公報、日本特開2012-41320號公報、日本特開2012-106986號公報、日本特開2012-153644號公報等記載之鋶鹽也可理想地使用。
作為含有式(1A)表示之陰離子之鋶鹽可列舉如下但不限於此等。又,下式中,Ac表示乙醯基、Ph表示苯基。
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式(1B)中,Rfb1及Rfb2各自獨立地表示氟原子、或也可以含有雜原子之碳數1~40之直鏈狀、分支狀或環狀之1價烴基。前述1價烴基可列舉和就前述R105之説明列舉者為同樣者。Rfb1及Rfb2較佳為氟原子或碳數1~4之直鏈狀氟化烷基。又,Rfb1與Rfb2也可彼此鍵結並和它們所鍵結之基(-CF2-SO2-N--SO2-CF2-)一起形成環,於此情形,Rfb1與Rfb2彼此鍵結而獲得之基宜為氟化伸乙基或氟化伸丙基較佳。
式(1C)中,Rfc1、Rfc2及Rfc3各自獨立地表示氟原子、或也可以含有雜原子之碳數1~40之直鏈狀、分支狀或環狀之1價烴基。前述1價烴基可列舉和就前述R105之説明列舉者為同樣者。Rfc1、Rfc2及Rfc3較佳為氟原子或碳數1~4之直鏈狀氟化烷基。又,Rfc1與Rfc2也可以互相鍵結並和它們所鍵結之基(-CF2-SO2-C--SO2-CF2-)一起形成環,於此情形,Rfc1與Rfc2互相鍵結合而獲得之基宜為氟化伸乙基或氟化伸丙基較佳。
式(1D)中,Rfd表示也可以含有雜原子之碳數1~40之直鏈狀、分支狀或環狀之1價烴基。前述1價烴基可列舉和就前述R105之説明列舉者為同樣者。
關於含式(1D)表示之陰離子之鋶鹽之合成詳見日本特開2010-215608號公報及特開2014-133723號公報。
作為含式(1D)表示之陰離子之鋶鹽可列舉如下但不限於此等。又,下式中,Ph表示苯基。
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又,含有式(1D)表示之陰離子之光酸產生劑,雖磺基之α位沒有氟但因為β位有2個三氟甲基,具有為了切斷光阻聚合物中之酸不安定基的充分酸性度。所以,可以作為光酸產生劑。
式(2)中,R201及R202各自獨立地表示也可以含有雜原子之碳數1~30之直鏈狀、分支狀或環狀之1價烴基。R203表示也可以含有雜原子之碳數1~30之直鏈狀、分支狀或環狀之2價烴基。又,R201、R202及R203中的任二者以上也可以互相鍵結並和它們所鍵結之硫原子一起形成環。LA表示單鍵、醚基、或也可以含有雜原子之碳數1~20之直鏈狀、分支狀或環狀之2價烴基。XA、XB、XC及XD各自獨立地表示氫原子、氟原子或三氟甲基。惟XA、XB、XC及XD中的至少一者表示氫原子以外之取代基。k表示0~3之整數。
前述1價烴基可列舉甲基、乙基、丙基、異丙基、正丁基、第二丁基、第三丁基、第三戊基、正戊基、正己基、正辛基、正壬基、正癸基、環戊基、環己基、2-乙基己基、環戊基甲基、環戊基乙基、環戊基丁基、環己基甲基、環己基乙基、環己基丁基、降莰基、氧雜降莰基、三環[5.2.1.02,6]癸基、金剛烷基、苯基、萘基、蒽基等。又,該等基之一部分氫原子也可取代為氧原子、硫原子、氮原子、鹵素原子等雜原子,或碳原子之一部分也可取代為氧原子、硫原子、氮原子等雜原子,其結果也可含有羥基、氰基、羰基、醚鍵、酯鍵、磺酸酯鍵、碳酸酯鍵、內酯環、磺內酯環、羧酸酐、鹵烷基等。
前述2價烴基可列舉亞甲基、伸乙基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基、庚烷-1,7-二基、辛烷-1,8-二基、壬烷-1,9-二基、癸烷-1,10-二基、十一烷-1,11-二基、十二烷-1,12-二基、十三烷-1,13-二基、十四烷-1,14-二基、十五烷-1,15-二基、十六烷-1,16-二基、十七烷-1,17-二基等直鏈狀烷二基;環戊烷二基、環己烷二基、降莰烷二基、金剛烷二基等飽和環狀2價烴基;伸苯基、伸萘基等不飽和環狀2價烴基等。又,該等基之一部分氫原子也可以取代為甲基、乙基、丙基、正丁基、第三丁基等烷基。又,該等基之一部分氫原子也可取代為含氧原子、硫原子、氮原子、鹵素原子等雜原子之基,或該等基之一部分之碳原子間也可插入含氧原子、硫原子、氮原子等雜原子之基,其結果也可以含有羥基、氰基、羰基、醚基、酯基、磺酸酯基、碳酸酯基、內酯環、磺內酯環、羧酸酐、鹵烷基等。前述雜原子宜為氧原子較佳。
式(2)表示之光酸產生劑宜為下式(2')表示者較佳。
式(2')中,LA同前述。LB表示氫原子或三氟甲基,較佳為三氟甲基。R301、R302及R303各自獨立地表示氫原子、或也可以含有雜原子之碳數1~20之直鏈狀、分支狀或環狀之1價烴基。前述1價烴基可列舉和就前述R105之説明列舉者為同樣者。x及y各自獨立地表示0~5之整數,z表示0~4之整數。
式(2)表示之光酸產生劑可列舉如下但不限於此等。又,下式中,LB同前述,Me表示甲基。
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[化80]
前述光酸產生劑之中,包括式(1A')或(1D)表示之陰離子者的酸擴散小且對於光阻溶劑之溶解性優良,特別理想。又,包括式(2')表示之陰離子者的酸擴散極小,特別理想。
酸產生劑之摻合量相對於基礎樹脂100質量份為0.01~100質量份較理想,0.1~80質量份更理想。酸產生劑可單獨使用1種或組合使用2種以上。
本發明之光阻材料也可以含有有機溶劑。前述有機溶劑可列舉日本特開2008-111103號公報之段落[0144]~[0145]記載之環己酮、甲基正戊酮等酮類;3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇、1-乙氧基-2-丙醇等醇類;丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇二甲醚、二乙二醇二甲醚等醚類;丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、乳酸乙
酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯等酯類;γ-丁內酯等內酯類等。該等溶劑可單獨使用1種也可混用2種以上。
有機溶劑之摻合量相對於基礎樹脂100質量份為50~10,000質量份較理想,100~5,000質量份更理想。
本發明之光阻材料也可以更含有鹼性化合物、溶解控制劑、界面活性劑、乙炔醇類等。
藉由於光阻材料摻合鹼性化合物,例如能抑制酸在光阻膜中之擴散速度且使解像度更提高。鹼性化合物可以列舉日本特開2008-111103號公報之段落[0146]~[0164]記載者。該等之中,1級、2級、3級胺化合物,尤其含有羥基、醚基、酯基、內酯環、氰基、磺酸酯基等之胺化合物較佳。鹼性化合物之摻合量相對於基礎樹脂100質量份為0~100質量份較理想,0.001~50質量份更理想。
藉由於光阻材料摻合界面活性劑,能更改善或控制光阻材料之塗佈性。界面活性劑可列舉日本特開2008-111103號公報之段落[0165]~[0166]記載者。界面活性劑之摻合量相對於基礎樹脂100質量份為0~10質量份較理想,0.0001~5質量份更理想。
藉由於光阻材料摻合溶解控制劑,能更加大曝光部與未曝光部之溶解速度之差距,能更提高解像度。溶解控制劑可以列舉日本特開2008-122932號公報之段落[0155]~[0178]記載者。溶解控制劑之摻合量相對於基礎樹脂100質量份為0~50質量份較理想,0~40質量份更理想。
乙炔醇類可以列舉段落[0179]~[0182]記載者。乙炔醇類之摻合量宜為光阻材料中之0~2質量%較理想,0.02~1質量%更理想。
本發明之光阻材料中,也可以摻合日本特開2008-239918號公報記載之聚合物型淬滅劑。其藉由配向在塗佈後之光阻表面,可提高圖案後之光阻之矩形性。聚合物型淬滅劑亦有防止當於光阻上使用保護膜時之圖案之膜損失、圖案頂部變圓之效果。含有前述聚合物型淬滅劑時,其摻合量可在不損及本發明效果之範圍內任意設定。
又,本發明之光阻材料中,也可以摻合下式(3)表示之α位未氟化之磺酸、或下式(4)表示之羧酸之鎓鹽作為淬滅劑。
式中,R151、R152及R153各自獨立地表示氫原子、不包括氟原子之鹵素原子、或也可以含有雜原子之碳數1~40之直鏈狀、分支狀或環狀之1價烴基。又,R151、R152及R153中之任二者以上也可以互相鍵結並和它們所鍵結之碳原子一起形成環。R154表示也可以含有雜原子之碳數1~40之直鏈狀、分支狀或環狀之1價烴基。M+表示鎓陽離子。
關於α位未氟化之磺酸之鎓鹽,詳見日本特開2008-158339號公報。產生α位未氟化之磺酸之光酸產生劑例如日本特開2010-155824號公報之段落[0019]~[0036]記載之化合物、日本特開2010-215608號公報之段落[0047]~[0082]記載之化合物。關於羧酸之鎓鹽詳見日本專利第3991462號公報。
式(3)或(4)中之陰離子為弱酸之共軛鹼。在此所指之弱酸,係無法使基礎樹脂使用之含酸不安定基之單元之酸不安定基脫保護之酸性度。式(3)或(4)表示之鎓鹽,當和具有如α位氟化之磺酸之強酸之共軛鹼作為相對陰離子之鎓鹽型光酸產生劑併用時,作為淬滅劑的作用。
亦即,當產生如α位氟化之磺酸之強酸的鎓鹽與產生如未經氟取代之磺酸、羧酸之弱酸之鎓鹽混用時,若因高能射線照射而從光酸產生劑產生之強酸和未反應之具弱酸陰離子之鎓鹽碰撞,會利用鹽交換放出弱酸,產生有強酸陰離子之鎓鹽。於此過程,強酸交換成催化能力較低的弱酸,故表觀上酸失活而可進行酸擴散之控制。
尤其,α位未氟化之磺酸及羧酸之鋶鹽及錪鹽因為有光分解性,光強度強之部分之淬滅能力降低且α位經氟化之磺酸、醯亞胺酸或甲基化酸之濃度增加。藉此,可以形成曝光部分之對比度提高,焦點深度(DOF)更改善之尺寸控制良好的圖案。
在此,產生強酸之光酸產生劑為鎓鹽時,可如前述,因高能射線照射產生之強酸交換為弱酸,但是據認為因高能射線照射產生之弱酸無法和未反應之產生強酸之鎓鹽碰撞並進行鹽交換。原因是鎓陽離子容易和較強酸之陰離子形成離子對的現象。
酸不安定基是對於酸特別敏感的縮醛時,為了使保護基脫離之酸不一定要是α位經氟化之磺酸、醯亞胺酸、甲基化酸,有時α位未氟化之磺酸也能進行脫保護反應。此時之淬滅劑無法使用磺酸之鎓鹽,如此的情形宜單獨使用羧酸之鎓鹽較佳。
作為α位未氟化之磺酸之鎓鹽、及羧酸之鎓鹽,各為下式(3')表示之磺酸之鎓鹽、及下式(4')表示之羧酸之鋶鹽為佳。
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式中,R251、R252及R253各自獨立地表示也可以含有雜原子之碳數1~20之直鏈狀、分支狀或環狀之1價烴基。又,R251、R252及R253中的任二者以上也可以互相鍵結並和它們所鍵結之原子及其間之原子一起形成環。R254表示也可以含有雜原子之碳數1~40之直鏈狀、分支狀或環狀之1價烴基。R255及R256各自獨立地表示氫原子或三氟甲基。R257及R258各自獨立地表示氫原子、氟原子或三氟甲基。R259表示氫原子、羥基、也可以含有雜原子之碳數1~35之直鏈狀、分支狀或環狀之1價烴基、或碳數6~30之取代或非取代之芳基。r表示1~3之整數。z1、z2及z3各自獨立地表示0~5之整數。
使用如此的鎓鹽作為淬滅劑時,可單獨使用1種或組合使用2種以上。其摻合量相對於基礎樹脂100質量份為0~50質量份較理想,0.001~50質量份更佳,0.01~20質量份更理想。藉由以前述範圍摻合如此的淬滅劑,容易調整光阻感度,此外,酸在光阻膜中之擴散速度受抑制,解像度提高,且可抑制曝光後之感度變化、或減少基板、環境依存性,能使曝光餘裕度、圖案輪廓等提升。又,藉由添加如此的淬滅劑,也可改善基板密合性。
本發明之光阻材料中,也可以摻合為了使旋塗後之光阻表面之撥水性提高的高分子化合物(撥水性改善劑)。撥水性改善劑可使用不使用面塗之浸潤微影使用者。撥水性改善劑宜為含有氟化烷基之高分子化合物、特定結構之含1,1,1,3,3,3-六氟-2-丙醇殘基之高分子化合物等較理想,列舉於日本特開2007-297590號公報、日本特開2008-111103號公報等。前述撥水性改善劑有必要溶於有機溶劑顯影液。前述特定之具1,1,1,3,3,3-六氟-2-丙醇殘基之撥水性改善劑對於顯影液之溶解性良好。就撥水性改善劑而言,將胺基、胺鹽作為重複單元而共聚合成的高分子化合物防止PEB中之酸蒸發而防止顯影後之孔圖案之開口不良之效果高。含有撥水性改善劑時,其摻合量相對於光阻材料之基礎樹脂100質量份為0.1~20質量份較理想,0.5~10質量份更理想。
藉由於含前述基礎聚合物之基礎樹脂中因應目的適當組合摻合酸產生劑、有機溶劑、溶解控制劑、鹼性化合物、界面活性劑等並構成光阻材料,於曝光部,前述基礎樹脂因觸媒反應而加快對於顯影液之溶解速度,故能成為極高感度之光阻材料。由本發明之光阻材料獲得之光阻膜之溶解對比度及解像性高,有曝光餘裕度,處理適應性優異、曝光後之圖案形狀良好且顯示更優良的蝕刻耐性,尤其能抑制酸擴散,故疏密尺寸差小,因而實用性高,作為超LSI用光阻材料非常有效。尤其,若摻合酸產生劑並製成利用了酸觸媒反應之化學增幅光阻材料,能成為更高感度,且各特性更優良,極為有用。
本發明之光阻材料,例如含前述基礎聚合物之基礎樹脂、酸產生劑、有機溶劑及鹼性化合物之化學增幅光阻材料,當使用在各種積體電路製造時,可採用公知之微影技術。
例如將本發明之光阻材料利用旋塗、輥塗、流塗、浸塗、噴塗、刮刀塗佈等適當塗佈方法塗佈在積體電路製造用之基板(Si、SiO2、SiN、SiON、TiN、WSi、BPSG、SOG、有機抗反射膜等)或遮罩電路製造用之基板(Cr、CrO、CrON、MoSi等)上,使塗佈膜厚成為0.1~2.0μm。將其於熱板上,較佳為60~150℃,進行10秒~30分鐘,更佳為80~120℃、30秒~20分鐘預烘。也可以在光阻膜上形成保護膜。保護膜宜可溶於鹼顯影液為較佳。顯影時進行光阻圖案之形成且同時進行保護膜之剝離。保護膜具有以下作用:減少來自光阻膜之散逸氣體之作用、作為遮斷從EUV雷射產生之13.5nm以外之波長140~300nm之頻外光(OOB)之濾器之作用、防止因環境影響而造成光阻之形狀變圓或膜損失之作用。其次,以選自紫外線、遠紫外線、EUV、EB、X射線、軟X射線、準分子雷射、γ線、同步加速放射線等高能射線中的光源將目的圖案通過預定遮罩曝光或直接曝光。曝光量以成為約1~200mJ/cm2,尤其約10~100mJ/cm2、或0.1~100μC/cm2,尤其約0.5~50μC/cm2的方式曝光較佳。然後,於熱板上進行60~150℃、10秒~30分鐘,較佳為80~120℃、30秒~20分鐘PEB。
又,使用0.1~10質量%,較佳為2~5質量%四甲基氫氧化銨(TMAH)、四乙基氫氧化銨(TEAH)、四丙基氫氧化銨(TPAH)、四丁基氫氧化銨(TBAH)等鹼水溶液之顯影液,進行3秒~3分鐘,較佳為5秒~2分鐘利用浸漬(dip)法、浸置(puddle)
法、噴霧(spray)法等常法的顯影,使已照光之部分溶於顯影液,未曝光之部分不溶解,而在基板上形成正型圖案。又,本發明之光阻材料,尤其在高能射線之中最適合利用EB、EUV、X射線、軟X射線、γ射線、同步加速放射線所為之微細圖案化。
比起一般廣泛使用之TMAH,烷基鏈加長的TEAH、TPAH、TBAH等有減少顯影中之膨潤而防止圖案崩塌的效果。日本專利第3429592號公報中,揭示為了將包括含有如甲基丙烯酸金剛烷酯之含脂環結構之重複單元與含如甲基丙烯酸第三丁酯之酸不安定基之重複單元,消除親水性基而撥水性高之聚合物之顯影,使用了TBAH水溶液之例。
TMAH顯影液最廣泛使用2.38質量%TMAH水溶液。其相當於0.26N,TEAH、TPAH、TBAH等水溶液亦為相同當量濃度較佳。成為0.26N之TEAH、TPAH及TBAH之質量各為3.84質量%、5.31質量%及6.78質量%。
於以EB或EUV解像之32nm以下之圖案中,會發生線扭轉、或線彼此纏結、或纏結的線崩塌的現象。據認為是因為顯影液中膨潤而膨大的線彼此巉結。膨潤的線含顯影液而像海綿般柔軟,容易因淋洗應力而崩塌。加長烷基鏈之顯影液有防止膨潤並防止圖案崩塌的效果。
也可以利用有機溶劑顯影獲得負型圖案。顯影液可以列舉2-辛酮、2-壬酮、2-庚酮、3-庚酮、4-庚酮、2-己酮、3-己酮、二異丁酮、甲基環己酮、苯乙酮、
甲基苯乙酮、乙酸丙酯、乙酸丁酯、乙酸異丁酯、乙酸戊酯、乙酸丁烯酯、乙酸異戊酯、甲酸丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊基、甲酸異戊酯、戊酸甲酯、戊烯酸甲酯、巴豆酸甲酯、巴豆酸乙酯、丙酸甲酯、丙酸乙酯、3-乙氧基丙酸乙酯、乳酸甲酯、乳酸乙酯、乳酸丙酯、乳酸丁酯、乳酸異丁酯、乳酸戊酯、乳酸異戊酯、2-羥基異丁酸甲酯、2-羥基異丁酸乙酯、苯甲酸甲酯、苯甲酸乙酯、乙酸苯酯、乙酸苄酯、苯基乙酸甲酯、甲酸苄酯、甲酸苯基乙酯、3-苯基丙酸甲酯、丙酸苄酯、苯基乙酸乙酯、乙酸2-苯基乙酯等。該等溶劑可以單獨使用1種或混用2種以上。
顯影結束時進行淋洗。淋洗液宜為和顯影液混溶且不使光阻膜溶解之溶劑較佳。如此的溶劑宜使用碳數3~10之醇、碳數8~12之醚化合物、碳數6~12之烷、烯、炔、芳香族系之溶劑較理想。
具體而言,碳數3~10之醇可列舉正丙醇、異丙醇、1-丁醇、2-丁醇、異丁醇、第三丁醇、1-戊醇、2-戊醇、3-戊醇、第三戊醇、新戊醇、2-甲基-1-丁醇、3-甲基-1-丁醇、3-甲基-3-戊醇、環戊醇、1-己醇、2-己醇、3-己醇、2,3-二甲基-2-丁醇、3,3-二甲基-1-丁醇、3,3-二甲基-2-丁醇、2-乙基-1-丁醇、2-甲基-1-戊醇、2-甲基-2-戊醇、2-甲基-3-戊醇、3-甲基-1-戊醇、3-甲基-2-戊醇、3-甲基-3-戊醇、4-甲基-1-戊醇、4-甲基-2-戊醇、4-甲基-3-戊醇、環己醇、1-辛醇等。
碳數8~12之醚化合物可以列舉二正丁醚、二異丁醚、二第二丁醚、二正戊醚、二異戊醚、二第二戊醚、二第三戊醚、二正己醚等。
作為碳數6~12之烷,可以列舉己烷、庚烷、辛烷、壬烷、癸烷、十一烷、十二烷、甲基環戊烷、二甲基環戊烷、環己烷、甲基環己烷、二甲基環己烷、環庚烷、環辛烷、環壬烷等。作為碳數6~12之烯,可以列舉己烯、庚烯、辛烯、環己烯、甲基環己烯、二甲基環己烯、環庚烯、環辛烯等。作為碳數6~12之炔,可以列舉、己炔、庚炔、辛炔等。
芳香族系之溶劑可列舉甲苯、二甲苯、乙苯、異丙苯、第三丁苯、均三甲苯等。
以下舉合成例、比較合成例、實施例及比較例對於本發明具體説明,但本發明不限於下列實施例。
[1]單體之合成
[合成例1]單體1之合成
將5,5-二甲基-2,4-唑啶二酮50g及4-(二甲胺基)吡啶3.7g溶解於THF500g,於冰冷下滴加甲基丙烯醯氯92.4g。於室溫攪拌5小時後加水並停止反應。通常之水系後處理後,利用矽膠管柱層析進行精製,獲得112g之單體1。
[化83]
[合成例2]單體2之合成
將2,4-四氫噻唑二酮45g及4-(二甲胺基)吡啶3.7g溶解於THF500g,於冰冷下滴加甲基丙烯醯氯92.4g。於室溫攪拌5小時後加水並停止反應。通常之水系後處理後,利用矽膠管柱層析進行精製,獲得110g之單體2。
[合成例3]單體3之合成
將玫瑰寧(Rhodanine)43g及4-(二甲胺基)吡啶3.7g溶於THF500g,於冰冷下滴加甲基丙烯醯氯92.4g。於室溫攪拌5小時後加水並停止反應。通常之水系後處理後,利用矽膠管柱層析進行精製,獲得106g之單體3。
[合成例4]單體4之合成
將5,5-二甲基-2-硫酮基-4-唑烷酮57g及4-(二甲胺基)吡啶3.7g溶於THF500g,於冰冷下滴加甲基丙烯醯氯92.4g。於室溫攪拌5小時後加水並停止反應。通常之水系後處理後,利用矽膠管柱層析進行精製,獲得114g之單體4。
[2]聚合物之合成
以下之合成例中,Mw係使用THF作為溶劑之凝膠滲透層析(GPC)獲得之聚苯乙烯換算測定值。又,以下之合成例使用之PAG單體1及2如下。
[合成例5]聚合物1之合成
於2L燒瓶中添加甲基丙烯酸1-異丙基外向四環[4.4.0.12,5.17,10]十二酯5.6g、甲基丙烯酸1-異丙基環戊酯3.9g、5.9g之單體1、甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯5.9g、及作為溶劑之THF 40g。將此反應容器於氮氣環境下冷卻到-70℃,重複3次減壓脫氣、吹氮。升溫到室溫後,添加作為聚合起始劑之AIBN 1.2g,升溫到60℃後使其進行15小時反應。將此反應溶液加到異丙醇1L,過濾沉澱的白色固體後,於60℃進行減壓乾燥,獲得白色聚合物(聚合物1)。
獲得之聚合物以13C-NMR、1H-NMR及GPC測定,獲得以下之分析結果。
‧共聚合組成比(莫耳比)
甲基丙烯酸1-異丙基外向四環[4.4.0.12,5.17,10]十二酯:甲基丙烯酸1-異丙基環戊酯:單體1:甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯=0.20:0.20:0.30:0.30
Mw=7,500
Mw/Mn=1.59
[合成例6]
於2L燒瓶中添加甲基丙烯酸1-異丙基外向四環[4.4.0.12,5.17,10]十二酯5.6g、甲基丙烯酸1-異丙基環戊酯3.9g、5.6g之單體2、甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯5.9g、及作為溶劑之THF 40g。將此反應容器於氮氣環境下冷卻到-70℃,重複3次減壓脫氣、吹氮。升溫到室溫後,添加作為聚合起始劑之AIBN 1.2g,升溫到60℃後進行15小時反應。將此反應溶液添加到異丙醇1L,過濾沉澱的白色固體後,於60℃進行減壓乾燥,獲得白色聚合物(聚合物2)。
將獲得之聚合物以13C-NMR、1H-NMR及GPC測定,獲得以下之分析結果。
‧共聚合組成比(莫耳比)
甲基丙烯酸1-異丙基外向四環[4.4.0.12,5.17,10]十二酯:甲基丙烯酸1-異丙基環戊酯:單體2:甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯=0.20:0.20:0.30:0.30
Mw=8,900
Mw/Mn=1.69
[合成例7]
於2L燒瓶中添加甲基丙烯酸1-乙基外向四環[4.4.0.12,5.17,10]十二酯5.5g、甲基丙烯酸1-第三丁基環戊酯4.2g、6.0g之單體3、甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯5.9g、及作為溶劑之THF 40g。將此反應容器於氮氣環境下冷卻到-70℃,重複3次減壓脫氣、吹氮。升溫到室溫後,添加作為聚合起始劑之AIBN 1.2g,升溫到60℃後,進行15小時反應。將此反應溶液添加到異丙醇1L,過濾沉澱之白色固體後,於60℃進行減壓乾燥,獲得白色聚合物(聚合物3)。
將獲得之聚合物以13C-NMR、1H-NMR及GPC測定,獲得以下之分析結果。
‧共聚合組成比(莫耳比)
甲基丙烯酸1-乙基外向四環[4.4.0.12,5.17,10]十二酯:甲基丙烯酸1-第三丁基環戊酯:單體3:甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯=0.20:0.20:0.30:0.30
Mw=8,600
Mw/Mn=1.81
[合成例8]
於2L燒瓶中添加甲基丙烯酸1-乙基外向四環[4.4.0.12,5.17,10]十二酯5.5g、甲基丙烯酸1-第三丁基環戊酯4.2g、6.4g之單體4、甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯5.9g、及作為溶劑之THF 40g。將此反應容器於氮氣環境下冷卻到-70℃,重複3次減壓脫氣、吹氮。升溫到室溫後,添加作為聚合起始劑之AIBN 1.2g,升溫到60℃後,進行15小時反應。將此反應溶液添加到異丙醇1L,過濾沉澱之白色固體後,於60℃進行減壓乾燥,獲得白色聚合物(聚合物4)。
將獲得之聚合物以13C-NMR、1H-NMR及GPC測定,獲得以下之分析結果。
‧共聚合組成比(莫耳比)
甲基丙烯酸1-乙基外向四環[4.4.0.12,5.17,10]十二酯:甲基丙烯酸1-第三丁基環戊酯:單體4:甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯=0.20:0.20:0.30:0.30
Mw=8,900
Mw/Mn=1.71
[合成例9]
於2L燒瓶中添加甲基丙烯酸1-(金剛烷-1-基)-1-甲基乙酯5.2g、4-(1-甲基環戊氧基)苯乙烯3.1g、5.9g之單體1、甲基丙烯酸4-羥基苯酯4.4g、11.0g之PAG單體1、及作為溶劑之THF 40g。將此反應容器於氮氣環境下冷卻到-70℃,重複3次減壓脫氣、吹氮。升溫到室溫後,添加作為聚合起始劑之AIBN 1.2g,升溫到60℃後,進行15小時反應。將此反應溶液添加到異丙醇1L,過濾沉澱之白色固體後,於60℃進行減壓乾燥,獲得白色聚合物(聚合物5)。
將獲得之聚合物以13C-NMR、1H-NMR及GPC測定,獲得以下之分析結果。
‧共聚合組成比(莫耳比)
甲基丙烯酸1-(金剛烷-1-基)-1-甲基乙酯:4-(1-甲基環戊氧基)苯乙烯:單體1:甲基丙烯酸4-羥基苯酯:PAG單體1=0.20:0.15:0.30:0.20:0.15
Mw=9,100
Mw/Mn=1.73
[合成例10]
於2L燒瓶中添加甲基丙烯酸4-(1-甲基環己氧基)苯酯10.9g、4.2g之單體2、甲基丙烯酸4-羥基苯酯3.6g、15.0g之PAG單體2、及作為溶劑之THF40g。將此反應容器於氮氣環境下冷卻到-70℃,重複3次減壓脫氣、吹氮。升溫到室溫後,添加作為聚合起始劑之AIBN 1.2g,升溫到60℃後,進行15小時反應。將此反應溶液添加到異丙醇1L,過濾沉澱之白色固體後,於60℃進行減壓乾燥,獲得白色聚合物(聚合物6)。
將獲得之聚合物以13C-NMR、1H-NMR及GPC測定,獲得以下之分析結果。
‧共聚合組成比(莫耳比)
甲基丙烯酸4-(1-甲基環己氧基)苯酯:單體2:甲基丙烯酸4-羥基苯酯:PAG單體2=0.40:0.20:0.20:0.20
Mw=8,300
Mw/Mn=1.83
[比較合成例1]
不使用單體1,除此以外依和合成例1同樣的方法合成比較聚合物1。
‧共聚合組成比(莫耳比)
甲基丙烯酸1-異丙基外向四環[4.4.0.12,5.17,10]十二酯:甲基丙烯酸1-異丙基環戊酯:甲基丙烯酸2-側氧基-4,5-二甲基四氫呋喃-4-酯=0.20:0.20:0.60
Mw=8,900
Mw/Mn=1.79
[比較合成例2]
將單體1替換為使用甲基丙烯酸2-側氧基四氫呋喃-3-酯,除此以外依和合成例9同樣的方法合成比較聚合物2。
‧共聚合組成比(莫耳比)
甲基丙烯酸1-(金剛烷-1-基)-1-甲基乙酯:4-(1-甲基環戊氧基)苯乙烯:甲基丙烯酸2-側氧基四氫呋喃-3-酯:甲基丙烯酸4-羥基苯酯:PAG單體1=0.20:0.15:0.30:0.20:0.15
Mw=9,100
Mw/Mn=1.78
[化95]
[3]ArF曝光圖案化評價
[實施例1-1~1-5、比較例1-1]
[3-1]光阻材料之製備
將於溶有100ppm之住友3M(股)製界面活性劑FC-4430之溶劑中以表1所示組成使各成分溶解而得之溶液以0.2μm尺寸之濾器過濾,製備成正型光阻材料(R-1~R-5)。
表1中之各組成如下。
有機溶劑:PGMEA(丙二醇單甲醚乙酸酯)GBL(γ-丁內酯)
酸產生劑:PAG1
淬滅劑:Quencher1
撥水性聚合物1:Mw=12,100、Mw/Mn=1.78
[化96]
[3-2]ArF曝光圖案化評價
將製備之光阻材料(R-1~R-5)旋塗於已在矽晶圓成膜信越化學工業(股)製旋塗式碳膜ODL-101(碳之含量為80質量%)160nm、於其上成膜含矽之旋塗式硬遮罩SHB-A940(矽之含量為43質量%)35nm的三層處理用之基板上,使用熱板於80℃進行60秒烘烤,製成厚度80nm之光阻膜。
將其使用ArF準分子雷射浸潤掃描曝光機(Nikon(股)製、NSR-610C、NA1.30、σ0.98/0.78、交叉極(crosspole)開口20度、Azimuthally偏光照明、6%半階調位相偏移遮罩、晶圓上尺寸節距90nm、線寬30nm之格子狀遮罩),邊使曝光
量變化邊曝光,曝光後,於表2所示溫度進行60秒PEB,邊使顯影噴嘴以30rpm旋轉邊噴出乙酸丁酯3秒,之後進行靜止浸置顯影27秒,旋乾獲得負型圖案。
以日立先端科技(股)製TDSEM(CG-4000)測定以溶劑顯影之圖像已反轉之孔圖案50處之尺寸,求出3σ之尺寸偏差。以日立先端科技(股)製電子顯微鏡S-4300觀察孔圖案之剖面形狀。結果如表2。
由表2所示結果可知本發明之光阻材料,有機溶劑顯影後之圖案之尺寸均勻性優異。
[4]EB描繪評價
[實施例2-1~2-2、比較例2-1]
[4-1]光阻材料之製備
將於溶有100ppm之住友3M(股)製界面活性劑FC-4430之溶劑中以表3所示組成使各成分溶解而得之溶液以0.2μm尺寸之濾器過濾,製備成正型光阻材料(R-6~R-8)。
表3中之各組成如下。
有機溶劑:PGMEA(丙二醇單甲醚乙酸酯)PGME(丙二醇單甲醚)CyH(環己酮)
鹼性化合物:Amine1
[4-2]EB描繪評價
將製備之正型光阻材料(R-6~R-8)使用Clean trackMark 5(東京威力科創(股)製)旋塗在直徑6吋φ之已蒸汽預處理六甲基二矽氮烷(HMDS)之Si基板上,於熱板上以110℃預烘60秒,製得厚度100nm之光阻膜。對其使用日立製作所(股)製HL-800D,以HV電壓50kV進行真空腔室內描繪。
描繪後立即使用Clean trackMark 5在熱板上,以表4記載之溫度進行60秒PEB,以2.38質量%之TMAH水溶液進行30秒浸置顯影,獲得正型圖案。
獲得之光阻圖案依如下方式評價。
定義100nm之線與間距以1:1解像之曝光量時之最小尺寸為解像力,以SEM測定100nmLS之邊緣粗糙度(LWR)。結果如表4。
Claims (8)
- 一種光阻材料,包含基礎樹脂,該基礎樹脂包括含有下式(a)表示之重複單元與羧基之氫原子取代為酸不安定基而得之重複單元及/或苯酚性羥基之氫原子取代為酸不安定基而得之重複單元且重量平均分子量為1,000~500,000之範圍之聚合物;
- 如申請專利範圍第1項之光阻材料,其中,該羧基之氫原子取代為酸不安定基而得之重複單元以下式(b1)表示,該苯酚性羥基之氫原子取代為酸不安定基而得之重複單元以下式(b2)表示;[化99]
- 如申請專利範圍第1或2項之光阻材料,其中,該聚合物更包括含有選自羥基、羧基、內酯環、碳酸酯基、硫碳酸酯基、羰基、環狀縮醛基、醚基、酯基、磺酸酯基、氰基、醯胺基、及-O-C(=O)-G-(G為-S-或-NH-)中之密合性基之重複單元。
- 如申請專利範圍第1或2項之光阻材料,其中,該聚合物更含有選自下式(d1)~(d3)中之至少1個重複單元;[化100]
- 如申請專利範圍第1或2項之光阻材料,更含有酸產生劑及有機溶劑。
- 如申請專利範圍第5項之光阻材料,更含有鹼性化合物及/或界面活性劑。
- 一種圖案形成方法,包括以下步驟:將如申請專利範圍第1至6項中任一項之光阻材料塗佈在基板上;加熱處理後以高能射線曝光;及使用顯影液進行顯影。
- 如申請專利範圍第7項之圖案形成方法,其中,該高能射線係i射線、KrF準分子雷射、ArF準分子雷射、電子束、或波長3~15nm之範圍之軟X射線。
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