JP2009258598A - 感放射線性組成物及びパターン形成方法 - Google Patents
感放射線性組成物及びパターン形成方法 Download PDFInfo
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- JP2009258598A JP2009258598A JP2008235209A JP2008235209A JP2009258598A JP 2009258598 A JP2009258598 A JP 2009258598A JP 2008235209 A JP2008235209 A JP 2008235209A JP 2008235209 A JP2008235209 A JP 2008235209A JP 2009258598 A JP2009258598 A JP 2009258598A
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Images
Abstract
【解決手段】酸解離性基が解離することでアルカリ可溶性となるアルカリ不溶性又は難溶性の重合体(A)を含有する感放射線性樹脂組成物であり、重合体(A)の、波長13.5nmにおける吸収係数が1.7μm−1以上であり、重合体(A)が、フッ素原子を含有しないフェノール構造の繰り返し単位を含むものである。
【選択図】なし
Description
本発明の感放射線性組成物は、化学増幅型ポジ型レジスト膜を成膜可能な材料として有用である。化学増幅型ポジ型レジスト膜においては、露光により酸発生剤から発生した酸の作用によって、重合体(A)中の酸解離性基が脱離し、重合体(A)がアルカリ可溶性となる。即ち、レジスト膜にアルカリ可溶性部位が形成される。このアルカリ可溶性部位はレジストの露光部であり、アルカリ現像液によって溶解及び除去することができるので、所望の形状のポジ型のレジストパターンを形成することができる。
(i):フッ素を含有しない、前記一般式(1)〜(3)からなる群より選択される少なくとも一の繰り返し単位(以下、「繰り返し単位(i)」ともいう)
(ii):前記一般式(4)で表される繰り返し単位(以下、「繰り返し単位(ii)」ともいう)
(iii):前記一般式(5)で表される繰り返し単位(但し、前記一般式(2)で表されるものを除く)(以下、「繰り返し単位(iii)」ともいう)
重合体(A)は、酸解離性基を有するものであり、それ自体はアルカリ不溶性又は難溶性の重合体である。この重合体(A)は、酸の作用により酸解離性基が解離して、アルカリ易溶性となる重合体である。なお、ここでいう「アルカリ不溶性又は難溶性」とは、重合体(A)を含有する感放射線性組成物から形成されたレジスト被膜からレジストパターンを形成する際に採用されるアルカリ現像条件下で、レジスト被膜の代わりに重合体(A)のみを用いた膜厚100nmの被膜を現像した場合に、この被膜の初期膜厚の50%以上が現像後に残存する性質を意味する。
重合体(A)の吸収係数=Σ{μa×(N0×ρ/A)} (X)
μa:原子の吸収係数
N0:アボガドロ定数(6.02×1023)
ρ:重合体の密度
A:原子量
(但し、原子の吸収係数μaは、Henkeらによって報告された値(Atomic Data and Nuclear Tables 54,(1993)181)を使用し、重合体の密度ρは、1.0g/cm3とする)
重合体(A)に含まれる繰り返し単位(i)は、一般式(1)〜(3)からなる群より選択される少なくとも一の繰り返し単位であり、フッ素を含有しない繰り返し単位である。
重合体(A)に含まれる繰り返し単位(ii)は、一般式(4)で表される繰り返し単位である。
重合体(A)に含まれる繰り返し単位(iii)は、一般式(5)で表される繰り返し単位である(但し、一般式(2)で表されるものを除く)。
重合体(A)には、前述の繰り返し単位(i)〜(iii)以外の、非酸解離性化合物に由来する繰り返し単位(以下、「繰り返し単位(iv)」ともいう)をその構造中に含むものであってもよい。
重合体(A)の合成方法は特に限定されないが、例えば、公知のラジカル重合又はアニオン重合により合成することができる。また、繰り返し単位(i)における側鎖中の水酸基は、加水分解されて水酸基を形成可能な基(例えば、アセトキシ基等)を有する重合体(A)前駆体を、有機溶媒中、塩基又は酸の存在下で加水分解することにより形成することができる。
本発明の感放射線性組成物には、前述の重合体(A)に加えて、通常、感放射線性酸発生剤(B)(以下、単に「酸発生剤(B)」ともいう)が更に含有される。この酸発生剤(B)は、リソグラフィープロセスにおいて照射される電子線や放射線等の作用により、感放射線性組成物内で酸を発生する物質である。そして、酸発生剤(B)から発生した酸の作用によって、重合体(A)中の酸解離性基が解離することになる。
本発明の感放射線性組成物には、酸拡散制御剤(C)を更に含有させることが好ましい。酸拡散制御剤(C)は、露光により酸発生剤(B)から生じる酸の、レジスト膜(レジスト被膜)中における拡散現象を制御し、非露光領域における好ましくない化学反応を抑制する作用を有する成分である。このような酸拡散制御剤(C)を含有させることにより、得られる感放射線性組成物の貯蔵安定性が向上し、また、形成したレジスト膜の解像度が更に向上するとともに、露光後から露光後の加熱処理までの引き置き時間(PED)の変動に起因するレジストパターンの線幅変化を抑えることができ、プロセス安定性に極めて優れた感放射線性組成物を得ることができる。
本発明の感放射線性組成物は、重合体(A)、並びに必要に応じて含有される酸発生剤(B)及び酸拡散制御剤(C)等の成分を、溶剤に溶解させたものであることが好ましい。溶剤は、直鎖状又は分岐状のケトン類、環状のケトン類、プロピレングリコールモノアルキルエーテルアセテート類、2−ヒドロキシプロピオン酸アルキル類、3−アルコキシプロピオン酸アルキル類、及びγ−ブチロラクトン等からなる群より選択される少なくとも一種が好ましい。
本発明の感放射線性組成物には、必要に応じて、界面活性剤、増感剤、脂肪族添加剤等の各種の添加剤(その他の成分)を更に含有させることができる。
本発明のパターン形成方法は、本発明の感放射線性組成物を基板上に塗布して、その膜厚が70nm以下のレジスト被膜を形成し、形成したレジスト被膜を露光した後、現像することを含む方法である。基板としては、シリコンウエハー、アルミニウムで被覆されたウェハー等を用いることができる。また、感放射線性組成物の潜在能力を最大限に引き出すため、例えば、特公平6−12452号公報(特開昭59−93448号公報)等に開示されているように、使用される基板上に有機系又は無機系の反射防止膜を形成することもできる。また、環境雰囲気中に含まれる塩基性不純物等の影響を防止するため、例えば、特開平5−188598号公報等に開示されているように、レジスト被膜上に保護膜を設けることもできる。なお、これらの技術は併用することもできる。
重合体(A)の吸収係数=Σ{μa×(N0×ρ/A)} (X)
μa:原子の吸収係数
N0:アボガドロ定数(6.02×1023)
ρ:重合体の密度
A:原子量
(但し、原子の吸収係数μaは、Henkeらによって報告された値(Atomic Data and Nuclear Tables 54,(1993)181)を使用し、重合体の密度ρは、1.0g/cm3とする)
3−メチル−1,3−ブタンジオール18.8g、1−アダマンタンカルボニルクロリド23.8g、及びピリジン11.1gをテトラヒドロフラン150gに溶解させた後、室温で6時間反応させた。反応終了後、反応母液に酢酸エチルを加え、有機層を水で洗浄した。その後、酢酸エチル/n−ヘキサン=1/1(体積比)の混合溶媒を展開溶媒として用いてシリカゲルカラムクロマトグラフィーを行なうことにより、アダマンタン残基を有する三級アルコール化合物を得た(収率:80%)。得られた三級アルコール化合物の構造確認を、1H−NMR(型番「JNM−ECA−400型」、日本電子社製)で行った。結果を以下に示す。
1H−NMR(400MHz、溶媒:DMSO−d6、内部標準:TMS):δ(ppm)=1.00〜1.10(s,6.0H)、1.50〜1.70(8.0H)、1.70〜1.80(6.0H)、1.85〜2.00(3.0H)、4.00〜4.10(t,2.0H)、2.25〜2.30(s,1.0H)
1H−NMR(400MHz、溶媒:DMSO−d6、内部標準:TMS):δ(ppm)=1.35〜1.50(s,6.0H)、1.50〜1.69(6.0H)、1.69〜1.85(9.0H)、1.85〜2.00(3.0H)、2.00〜2.15(t,2.0H)、4.00〜4.10(t,2.0H)、5.60〜6.00(2.0H)
p−アセトキシスチレン140g、単量体(M−1−1)80g、アゾビスイソブチロニトリル(AIBN)8g、及びt−ドデシルメルカプタン1gを、プロピレングリコールモノメチルエーテル200gに溶解した後、窒素雰囲気下、反応温度を70℃に保持して、16時間重合させた。重合後、反応溶液を1000gのn−ヘキサン中に滴下して、生成した重合体を凝固精製した。この重合体に、再度プロピレングリコールモノメチルエーテル150gを加えた後、メタノール300g、トリエチルアミン80g及び水15gを加え、沸点にて還流させながら8時間加水分解反応を行なった。反応後、溶剤及びトリエチルアミンを減圧留去し、得られた重合体をアセトンに溶解した後、2000gの水中に滴下して凝固させ、生成した白色粉末をろ過して、減圧下、50℃で一晩乾燥した。
4−アセトキシスチレン10.25g、1,1,1,3,3,3−ヘキサフルオロ−2−(4−ビニルフェニル)プロパン−2−オン17.06g、2−エチルアダマンチルアクリレート12.69g、AIBN1.186g、及びt−ドデシルメルカプタン0.474gを、プロピレングリコールモノメチルエーテル40gに溶解した後、窒素雰囲気下、70℃で3時間、75℃で3時間、95℃で1時間撹拌することにより重合させた。重合後、反応溶液を1000gのヘキサン中に滴下して、生成した重合体を凝固精製した。乾燥した重合体30gに、40gのプロピレングリコールモノメチルエーテルを再度加えた後、更にメタノール70g、トリエチルアミン6.5g、及び水1.2gを加え、沸点にて還流させながら、8時間加水分解反応を行なった。加水分解反応後、溶剤及びトリエチルアミンを減圧留去して重合体を得た。得られた重合体を、固形分濃度が20%となるように酢酸エチルに溶解した後、1000gのヘキサンに滴下して凝固させた。生成した白色粉末をろ過して、減圧下50℃で一晩乾燥することにより最終生成物である重合体(A−2)を得た。
4−アセトキシスチレン123.6g、2−エチルアダマンチルアクリレート56.4g、AIBN6.59g、及びt−ドデシルメルカプタン2.17gを、プロピレングリコールモノメチルエーテル180gに溶解した後、窒素雰囲気下、70℃で3時間、75℃で3時間、95℃で1時間撹拌することにより重合させた。重合後、反応溶液を4000gのヘキサン中に滴下して、生成した重合体を凝固精製した。乾燥した重合体140gに、180gのプロピレングリコールモノメチルエーテルを再度加えた後、更にメタノール300g、トリエチルアミン30g、及び水5.4gを加え、沸点にて還流させながら、8時間加水分解反応を行なった。加水分解反応後、溶剤及びトリエチルアミンを減圧留去して重合体を得た。得られた重合体を、固形分濃度が20%となるように酢酸エチルに溶解した後、4000gのヘキサンに滴下して凝固させた。生成した白色粉末をろ過して、減圧下50℃で一晩乾燥することにより最終生成物である重合体(A−3)を得た。
4−アセトキシスチレン9.02g、1,1,1,3,3,3−ヘキサフルオロ−2−(4−ビニルフェニル)プロパン−2−オン15.03g、単量体(M−1−1)15.95g、AIBN1.044g、及びt−ドデシルメルカプタン0.319gを、プロピレングリコールモノメチルエーテル40gに溶解した後、窒素雰囲気下、70℃で3時間、75℃で3時間、95℃で1時間撹拌することにより重合させた。重合後、反応溶液を1000gのヘキサン中に滴下して、生成した重合体を凝固精製した。乾燥した重合体30gに、40gのプロピレングリコールモノメチルエーテルを再度加えた後、更にメタノール70g、トリエチルアミン6.5g、及び水1.2gを加え、沸点にて還流させながら、8時間加水分解反応を行なった。加水分解反応後、溶剤及びトリエチルアミンを減圧留去して重合体を得た。得られた重合体を、固形分濃度が20%となるように酢酸エチルに溶解した後、1000gのヘキサンに滴下して凝固させた。生成した白色粉末をろ過して、減圧下50℃で一晩乾燥することにより最終生成物である重合体(A−4)を得た。
4−アセトキシスチレン11.97g、1,1,1,3,3,3−ヘキサフルオロ−2−(4−ビニルフェニル)プロパン−2−オン19.93g、tert−ブチルアクリレート8.11g、AIBN1.385g、及びt−ドデシルメルカプタン0.319gを、プロピレングリコールモノメチルエーテル40gに溶解した後、窒素雰囲気下、70℃で3時間、75℃で3時間、95℃で1時間撹拌することにより重合させた。重合後、反応溶液を1000gのヘキサン中に滴下して、生成した重合体を凝固精製した。乾燥した重合体30gに、40gのプロピレングリコールモノメチルエーテルを再度加えた後、更にメタノール70g、トリエチルアミン6.5g、及び水1.2gを加え、沸点にて還流させながら、8時間加水分解反応を行なった。加水分解反応後、溶剤及びトリエチルアミンを減圧留去して重合体を得た。得られた重合体を、固形分濃度が20%となるように酢酸エチルに溶解した後、1000gのヘキサンに滴下して凝固させた。生成した白色粉末をろ過して、減圧下50℃で一晩乾燥することにより最終生成物である重合体(A−5)を得た。
重合体(A−2)100部、酸発生剤(B−1)9部、酸拡散制御剤(C−2)2.6部、溶剤(D−1)2300部、及び溶剤(D−2)1000部を混合して得た溶液を、孔径200nmのメンブランフィルターで濾過して、感放射線性組成物(実施例1)を調製した。調製した感放射線性組成物を用いてレジストパターンを形成した。なお、レジスト被膜の膜厚は60nmとした。レジストパターンを形成する際の感度(最適露光量)は22mJ/cm2であり、レジストパターンのΔCDは8nmであった。
表1に示す配合処方としたこと及びレジスト被膜の膜厚としたこと以外は、前述の実施例1と同様の操作により感放射線性組成物(実施例2〜6、比較例1〜6)を調製した。調製した感放射線性組成物の感度(最適露光量)及びΔCDの測定結果を表1に示す。なお、感放射線性組成物の調製に際して使用した各成分の詳細を以下に示す。
(B−1):トリフェニルスルホニウムトリフルオロメタンスルホネート
(C−1):トリ−n−オクチルアミン
(C−2):トリフェニルスルホニウムサリチレート
(D−1):乳酸エチル
(D−2):プロピレングリコールモノメチルエーテルアセテート
Claims (3)
- 酸解離性基を有し、前記酸解離性基が解離することでアルカリ可溶性となるアルカリ不溶性又は難溶性の重合体(A)を含有し、
前記重合体(A)の、波長13.5nmにおける吸収係数が1.7μm−1以上であり、
前記重合体(A)が、下記(i)〜(iii)の繰り返し単位を含むものである感放射線性組成物。
(i):フッ素を含有しない、下記一般式(1)〜(3)からなる群より選択される少なくとも一の繰り返し単位
(ii):下記一般式(4)で表される繰り返し単位
(iii):下記一般式(5)で表される繰り返し単位(但し、前記一般式(2)で表されるものを除く)
- 請求項1に記載の感放射線性組成物を基板上に塗布して、その膜厚が70nm以下のレジスト被膜を形成し、形成した前記レジスト被膜を露光した後、現像することを含むパターン形成方法。
- その膜厚が5〜20nmの前記レジスト被膜を形成する請求項2に記載のパターン形成方法。
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TWI650310B (zh) * | 2014-02-14 | 2019-02-11 | 日商三菱瓦斯化學股份有限公司 | 新穎脂環式酯化合物之製造方法、新穎脂環式酯化合物、該化合物所聚合而成之(甲基)丙烯酸酯共聚物、及含該共聚物之感光性樹脂組成物 |
JP2015219246A (ja) * | 2014-05-13 | 2015-12-07 | Jsr株式会社 | パターン形成方法 |
JP2017181928A (ja) * | 2016-03-31 | 2017-10-05 | Jsr株式会社 | ポジ型感放射線性樹脂組成物、層間絶縁膜、層間絶縁膜の形成方法、半導体素子及び表示素子 |
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