JP5660037B2 - 感放射線性樹脂組成物 - Google Patents
感放射線性樹脂組成物 Download PDFInfo
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- JP5660037B2 JP5660037B2 JP2011514394A JP2011514394A JP5660037B2 JP 5660037 B2 JP5660037 B2 JP 5660037B2 JP 2011514394 A JP2011514394 A JP 2011514394A JP 2011514394 A JP2011514394 A JP 2011514394A JP 5660037 B2 JP5660037 B2 JP 5660037B2
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003440 styrenes Chemical class 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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- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- HXINNZFJKZMJJJ-UHFFFAOYSA-N tert-butyl n-[12-[(2-methylpropan-2-yl)oxycarbonylamino]dodecyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCCCNC(=O)OC(C)(C)C HXINNZFJKZMJJJ-UHFFFAOYSA-N 0.000 description 1
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- NMEQKHOJGXGOIL-UHFFFAOYSA-N tert-butyl n-[7-[(2-methylpropan-2-yl)oxycarbonylamino]heptyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCNC(=O)OC(C)(C)C NMEQKHOJGXGOIL-UHFFFAOYSA-N 0.000 description 1
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- XSIWKTQGPJNJBV-UHFFFAOYSA-N tert-butyl n-[9-[(2-methylpropan-2-yl)oxycarbonylamino]nonyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCNC(=O)OC(C)(C)C XSIWKTQGPJNJBV-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 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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- 238000005406 washing Methods 0.000 description 1
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- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
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- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
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Description
本発明の感放射線性樹脂組成物は、樹脂(A)と、カルボン酸発生剤(C)と、を含有するものであり、酸発生剤(B)と、を更に含有するものであることが好ましい。
樹脂(A)は、酸解離性基を有する繰り返し単位を有し、通常、アルカリ不溶性又はアルカリ難溶性であり、酸の作用によりアルカリ易溶性となる樹脂である。尚、ここでいう「アルカリ不溶性又はアルカリ難溶性」とは、樹脂(A)を含有する感放射線性樹脂組成物を用いて形成し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樹脂(A)のみを用いた膜厚100nmの被膜を現像した場合に、被膜の初期膜厚の50%以上が現像後に残存する性質をいう。
樹脂(A)は、前記一般式(6)で表される繰り返し単位、及び一般式(7)で表される繰り返し単位のうちの少なくとも一の繰り返し単位(以下、「繰り返し単位(1)」ともいう)を有することが好ましい。
樹脂(A)の調製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行うことができる。また、繰り返し単位(2)〜(4)における側鎖のヒドロキシスチレン単位は、重合反応終了後、有機溶媒中で塩基又は酸の存在下でアセトキシ基等の加水分解を行なうことにより得ることもできる。
樹脂(A)の、ゲルパーミエーションクロマトグラフィー(GPC)で測定したポリスチレン換算の重量平均分子量(以下、「Mw」ともいう)は、3000〜100000であることが好ましく、3000〜40000であることがより好ましく、3000〜25000であることが更に好ましい。また、樹脂(A)のMwと、GPCで測定したポリスチレン換算の数平均分子量(以下、「Mn」ともいう)との比(Mw/Mn)は、通常、1〜5であり、1〜3であることが好ましく、1〜2.5であることが更に好ましい。
酸発生剤(B)は、リソグラフィープロセスにおいて、感放射線性樹脂組成物を用いて形成したレジスト被膜に電子線や放射線等を照射することによって、レジスト被膜内でpKaが2以下の酸を発生するものである。また、放射線の照射により発生する酸のpKaは、0以下であることが好ましい。なお、放射線の照射により発生する酸のpKaの下限値は特に限定されるものではないが、通常、−15以上である。
カルボン酸発生剤(C)は、通常、塩基性を示すが、リソグラフィープロセスにおいて、レジスト被膜に電子線や放射線等を照射することによって、レジスト被膜内でカルボン酸を発生し、塩基性を失う物質であり、前記一般式(1)で表される化合物である。
カルボン酸発生剤(C)の合成方法は特に限定されるものではないが、例えば、下記反応式で表されるように、一般式(13)で表される化合物を、水溶液中、炭酸ナトリウムと反応させることにより、一般式(14)で表される化合物とし、更に、所望のオニウムカチオンM+のハロゲン化物(例えば、M+Br−)と水溶液中にて反応させることにより合成することができる。
本発明の感放射線性樹脂組成物は、酸拡散制御剤(D)を更に含有することが好ましい。酸拡散制御剤(D)は、露光により酸発生剤(B)から生じる酸の、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ものである。
本発明の感放射線性樹脂組成物は、樹脂(A)、酸発生剤(B)、及びカルボン酸発生剤(C)を、溶剤に溶解させたものであることが好ましい。即ち、その他の成分として溶剤を更に含有することが好ましい。また、本発明の感放射線性樹脂組成物は、その他の成分として、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を更に含有させることができる。
本発明の感放射線性樹脂組成物は、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(B)から発生した酸の作用によって、樹脂(A)中の酸解離性基が脱離し、樹脂(A)がアルカリ可溶性となる。即ち、レジスト被膜に、アルカリ可溶性部位が生じる。このアルカリ可溶性部位は、レジストの露光部であり、この露光部はアルカリ現像液によって溶解、除去することができる。このようにして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。以下、具体的に説明する。
p−アセトキシスチレン56g、式(M−1)で表される化合物(以下、「化合物(M−1)」ともいう)44g、アゾビスイソブチロニトリル(以下、「AIBN」という)4g、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100g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、共重合体を凝固精製した。次いで、この共重合体に、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、更に、メタノール150g、トリエチルアミン35g、及び水7gを加えて、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、得られた共重合体をアセトン150g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。得られた共重合体は、Mwが11000であり、Mw/Mnが2.0であり、13C−NMR分析の結果、p−ヒドロキシスチレンに由来する繰り返し単位及び化合物(M−1)に由来する繰り返し単位の含有比(mol比)が65:35の共重合体であった。以下、この共重合体を、樹脂(A−1)とする。
p−アセトキシスチレン55g、式(M−2)で表される化合物(以下、「化合物(M−2)」ともいう)45g、AIBN4g、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100g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、共重合体を凝固精製した。次いで、この共重合体に、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、更に、メタノール150g、トリエチルアミン34g、及び水6gを加えて、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、得られた共重合体をアセトン150g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。得られた共重合体は、Mwが10000であり、Mw/Mnが2.1であり、13C−NMR分析の結果、p−ヒドロキシスチレンに由来する繰り返し単位及び化合物(M−2)に由来する繰り返し単位の含有比(mol比)が65:35の共重合体であった。以下、この共重合体を、樹脂(A−2)とする。
合成例1で調製した樹脂(A−1)100部、酸発生剤(B−1)15部、カルボン酸発生剤(C−1)5部、酸拡散制御剤(D−1)2部、溶剤(E−1)1100部、及び溶剤(E−2)2500部を混合し、得られた混合液を孔径200nmのメンブランフィルターでろ過することにより、感放射線性樹脂組成物の組成物溶液を調製した。
表1に示す仕込み量にて、樹脂(A)、酸発生剤(B)、カルボン酸発生剤(C)、酸拡散制御剤(D)、溶剤(E)を混合し、得られた混合液を孔径200nmのメンブランフィルターでろ過することにより、各感放射線性樹脂組成物の組成物溶液を調製した。
(B−1):式(B−1)で表される化合物
(B−2):式(B−2)で表される化合物
(C−1):式(C−1)で表される化合物
(C−2):式(C−2)で表される化合物
(C−3):式(C−3)で表される化合物
(D−1):トリ−n−オクチルアミン
(E−1):乳酸エチル
(E−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
半導体製造装置(東京エレクトロン社製のクリーントラックACT−8)内で、シリコンウエハー上に感放射線性樹脂組成物の組成物溶液をスピンコートした後、表2に示す条件でPB(加熱処理)を行い、膜厚50nmのレジスト被膜を形成した。その後、簡易型の電子線描画装置(日立製作所社製、型式「HL800D」、出力;50KeV、電流密度;5.0アンペア/cm2)を用いてレジスト被膜に電子線を照射した。電子線の照射後、表2に示す条件でPEBを行った。その後、2.38%テトラメチルアンモニウムヒドロキシド水溶液を用い、23℃で1分間、パドル法により現像した後、純水で水洗し、乾燥して、レジストパターンを形成した。このようにして形成したレジストパターンについて評価試験を行った。評価結果を表2に示す。
まず、前記式(M−3)で表される化合物(化合物(M−3))50.4g(50mol%)、前記式(M−6)で表される化合物(化合物(M−6))12.4g(15mol%)、及び前記式(M−1)で表される化合物(化合物(M−1))37.2g(35mol%)を、2−ブタノン200gに溶解して溶解溶液を得た。得られた溶解溶液にAIBN7.45gを投入して単量体溶液を得た。
表3に示す配合処方としたこと以外は合成例3と同様にして各共重合体を得た。なお、各共重合体の収量及び収率を表3に併せて記す。得られた共重合体をそれぞれ樹脂(A−4)〜(A−6)とし、各樹脂の物性値を表4に記す。
前記式(M−6)で表される化合物(化合物(M−6))31.6g(35mol%)、前記式(M−7)で表される化合物(化合物(M−7))6.5g(10mol%)、及び前記式(M−3)で表される化合物(化合物(M−3))45.83g(45mol%)を、2−ブタノン200gに溶解して溶解溶液を得た。得られた溶解溶液にAIBN8.1gを投入して単量体溶液を得た。
表3に示す配合処方としたこと以外は合成例3と同様にして共重合体を得た。なお、共重合体の収量及び収率を表3に併せて記す。得られた共重合体を樹脂(A−8)とし、その物性値を表4に記す。
表3に示す配合処方としたこと以外は合成例7と同様にして各共重合体を得た。なお、各共重合体の収量及び収率を表3に併せて記す。得られた各共重合体をそれぞれ樹脂(A−9)〜(A−10)とし、各樹脂の物性値を表4に記す。
表3に示す配合処方としたこと以外は合成例3と同様にして共重合体を得た。なお、共重合体の収量及び収率を表3に併せて記す。得られた共重合体を樹脂(A−8)とし、その物性値を表4に記す。
表3に示す配合処方としたこと以外は合成例7と同様にして各共重合体を得た。なお、各共重合体の収量及び収率を表3に併せて記す。得られた各共重合体をそれぞれ樹脂(A−12)〜(A−14)とし、各樹脂の物性値を表4に記す。
前記式(M−9)で表わされる化合物(化合物(M−9))37.4g(40mol%)、及び前記式(M−10)で表わされる化合物(化合物(M−10))62.6g(60mol%)を、2−ブタノン100gに溶解して溶解溶液を得た。得られた溶解溶液にジメチル−2,2’−アゾビスイソブチレート4.8gを投入して単量体溶液を準備した。
表5に示す配合量で調整した後、孔径0.05μmのフィルターでろ過して実施例6〜19及び比較例4〜6の感放射線性樹脂組成物を得た。得られた感放射線性樹脂組成物について各種評価を行った。評価結果を表6に示す。
(C−1):前記式(C−1)で表される化合物
(C−2):前記式(C−2)で表される化合物
(C−3):前記式(C−3)で表される化合物
(E−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
(E−3):式(E−3)で表される化合物(シクロヘキサノン)
(E−4):式(E−4)で表される化合物(γ−ブチロラクトン)
Claims (6)
- (B)放射線の照射によりpKaが2以下の酸を発生する感放射線性酸発生剤を更に含有する請求項1に記載の感放射線性樹脂組成物。
- 前記(B)感放射線性酸発生剤が、放射線の照射によりスルホン酸を発生するスルホン酸発生剤である請求項2に記載の感放射線性樹脂組成物。
- 前記(A)酸解離性基含有樹脂が、
下記一般式(3)で表される繰り返し単位、下記一般式(4)で表される繰り返し単位、及び下記一般式(5)で表される繰り返し単位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を有するものである請求項1〜3のいずれか一項に記載の感放射線性樹脂組成物。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62195324A (ja) * | 1985-11-29 | 1987-08-28 | ア−ル.ピ−.シエラ− コ−ポレイシヨン | 目標とする腸への投与システム |
JPH05181279A (ja) * | 1991-04-30 | 1993-07-23 | Toshiba Corp | パターン形成用レジストおよびパターン形成方法 |
JPH11125907A (ja) * | 1997-08-18 | 1999-05-11 | Jsr Corp | 感放射線性樹脂組成物 |
JP2005274647A (ja) * | 2004-03-23 | 2005-10-06 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3224148A1 (de) * | 1982-06-29 | 1983-12-29 | Hoechst Ag, 6230 Frankfurt | Quartaere ammoniumsalze und deren verwendung als stroemungsbeschleuniger |
US4910122A (en) | 1982-09-30 | 1990-03-20 | Brewer Science, Inc. | Anti-reflective coating |
JPH0612452B2 (ja) | 1982-09-30 | 1994-02-16 | ブリュ−ワ−・サイエンス・インコ−ポレイテッド | 集積回路素子の製造方法 |
US4822718A (en) | 1982-09-30 | 1989-04-18 | Brewer Science, Inc. | Light absorbing coating |
JPS59169889A (ja) * | 1983-03-16 | 1984-09-25 | Ricoh Co Ltd | 感熱記録材料 |
DE3345806A1 (de) * | 1983-12-17 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | Oxalkylierte quaternaere ammonium-verbindungen, verfahren zu deren herstellung und deren verwendung als stroemungsbeschleuniger |
US5674648A (en) | 1984-08-06 | 1997-10-07 | Brewer Science, Inc. | Anti-reflective coating |
US5403695A (en) | 1991-04-30 | 1995-04-04 | Kabushiki Kaisha Toshiba | Resist for forming patterns comprising an acid generating compound and a polymer having acid decomposable groups |
DE69214035T2 (de) | 1991-06-28 | 1997-04-10 | Ibm | Reflexionsverminderde Überzüge |
JPH05323590A (ja) * | 1992-05-20 | 1993-12-07 | Fujitsu Ltd | 化学増幅型レジスト組成物 |
KR100551653B1 (ko) | 1997-08-18 | 2006-05-25 | 제이에스알 가부시끼가이샤 | 감방사선성수지조성물 |
JP2001166478A (ja) * | 1999-12-03 | 2001-06-22 | Jsr Corp | 感放射線性樹脂組成物 |
ES2190373B1 (es) * | 2001-12-07 | 2004-10-16 | J. URIACH & CIA, S.A. | Uso del acido 2-hidroxi- o 2-acetiloxi-4-trifluorometilbenzoico como agente para el tratamiento y prevencion del deterioro cognitivo ligero. |
US20040047905A1 (en) * | 2002-09-06 | 2004-03-11 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Personal care towelette tablet |
JP2007297284A (ja) * | 2006-04-27 | 2007-11-15 | Jsr Corp | スルホニウム塩化合物および感放射線性樹脂組成物 |
JPWO2008066011A1 (ja) * | 2006-11-28 | 2010-03-04 | Jsr株式会社 | ポジ型感放射線性樹脂組成物およびパターン形成方法 |
-
2010
- 2010-05-14 KR KR1020117024507A patent/KR101716913B1/ko active IP Right Grant
- 2010-05-14 JP JP2011514394A patent/JP5660037B2/ja active Active
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-
2011
- 2011-11-04 US US13/288,963 patent/US8968980B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62195324A (ja) * | 1985-11-29 | 1987-08-28 | ア−ル.ピ−.シエラ− コ−ポレイシヨン | 目標とする腸への投与システム |
JPH05181279A (ja) * | 1991-04-30 | 1993-07-23 | Toshiba Corp | パターン形成用レジストおよびパターン形成方法 |
JPH11125907A (ja) * | 1997-08-18 | 1999-05-11 | Jsr Corp | 感放射線性樹脂組成物 |
JP2005274647A (ja) * | 2004-03-23 | 2005-10-06 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
Non-Patent Citations (1)
Title |
---|
JPN6014020279; Rixt T. Buwalda: 'Wormlike Micellar and Vesicular Phases in Aqueous Solutions of Single-Tailed Surfactants with Aromat' Langmuir 2000,16, 20000601, p6780-6786 * |
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