JP4225427B2 - 開環メタセシス重合体水素添加物、それを含有するレジスト材料及びパターン形成方法 - Google Patents
開環メタセシス重合体水素添加物、それを含有するレジスト材料及びパターン形成方法 Download PDFInfo
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- JP4225427B2 JP4225427B2 JP2006264264A JP2006264264A JP4225427B2 JP 4225427 B2 JP4225427 B2 JP 4225427B2 JP 2006264264 A JP2006264264 A JP 2006264264A JP 2006264264 A JP2006264264 A JP 2006264264A JP 4225427 B2 JP4225427 B2 JP 4225427B2
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Images
Classifications
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- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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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
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Description
特にArFエキシマレーザーはKrFエキシマレーザーの次世代の光源として、90nm〜45nmノードの先端半導体用フォトリソグラフィーに不可欠と広く認知されている。
ArFエキシマレーザーを光源としたフォトリソグラフィーにおいては、KrFエキシマレーザー光源世代のレジスト材料用樹脂の主役であったポリヒドロキシスチレン誘導体が波長193nmに不透明であるとの理由から適用困難であり、ベース樹脂の透明性の確保が不可欠となっている。
で表される構造単位[A]と、下記一般式[3]及び/又は[4]
から選ばれる構造単位[B]と、下記一般式[5]及び/又は[6]
から選ばれる構造単位[C]とから構成され、かつ、構造単位[A]の一般式[1]のX1、構造単位[B]の一般式[3]のX2、及び一般式[4]のX3のうち少なくとも1つが−O−であり、その構成モル比が[A]/([B]+[C])=20/80〜98/2、([A]+[B])/[C]=99/1〜50/50、([A]+[C])/[B]=99/1〜21/79を同時に満たす開環メタセシス重合体水素添加物。
(2)一般式[1]のR1〜R4のうち少なくとも一つとして選ばれる一般式[2]中のR6が、1−アルキルシクロペンチル基、2−アルキル−2−ノルボルニル基又は2−アルキル−2−アダマンチル基である(1)に記載の開環メタセシス重合体水素添加物。
(3)一般式[7]
で表される構造単位[D]を更に含む請求項1または2に記載の開環メタセシス重合体水素添加物。
(4)一般式[1]で表される構造単位[A]、一般式[3]及び/又は[4]で表される構造単位[B]、一般式[5]及び/又は[6]で表される構造単位[C]の合計と、一般式[7]で表される構造単位[D]との構成モル比が([A]+[B]+[C])/[D]=100/0〜20/80である(3)に記載の開環メタセシス重合体水素添加物。
(5)一般式[9]
で表される構造単位[E]を更に含む(1)ないし(4)のいずれかに記載の開環メタセシス重合体水素添加物。
(6)一般式[1]で表される構造単位[A]、一般式[3]及び/又は[4]で表される構造単位[B]、一般式[5]及び/又は[6]で表される構造単位[C]の合計と、一般式[9]で表される構造単位[E]との構成モル比が([A]+[B]+[C])/[E]=100/0〜40/60である(5)に記載の開環メタセシス重合体水素添加物。
(7)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数平均分子量が2,000〜200,000である(1)ないし(6)のいずれかに記載の開環メタセシス重合体水素添加物。
(8)GPCで測定したポリスチレン換算の数平均分子量が3,000〜50,000である(7)に記載の開環メタセシス重合体水素添加物。
(9)前記(1)ないし(8)のいずれかに記載の開環メタセシス重合体水素添加物をベース樹脂として含有するレジスト材料。
(10)前記(1)ないし(8)のいずれかに記載の開環メタセシス重合体水素添加物をベース樹脂として含有するレジスト材料を基板上に塗布する工程と、加熱処理後フォトマスクを介して高エネルギー線もしくは電子線で露光する工程と、必要に応じて加熱処理した後、現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
で表される1−アルキルシクロアルキル基、下記一般式[15]
で表される2−アルキル−2−ノルボルニル基、及び2−メチル−2−アダマンチル及び2−エチル−2−アダマンチル等の2−アルキル−2−アダマンチル基が挙げられる。
で表される構造単位[B−3−1]及び[B−3−2]及び/又は下記一般式[4−1]及び[4−2]
で表される構造単位[B−4−1]及び[B−4−2]と、一般式[5]及び/又は[6]で表される構造単位[C]から成る開環メタセシス重合体水素添加物とすることができる。
で表される構造単位[D]を更に構造単位として有していることが、基盤密着性及び現像液への親和性が更に向上するために好ましい。
で表される構造単位[E]を更に構造単位として有してもよい。
で表される構造単位[F]を更に構造単位として有してもよい。
i.下記一般式(P1a−1)、(P1a−2)又は(P1b)のオニウム塩、
ii.下記一般式(P2)のジアゾメタン誘導体、
iii.下記一般式(P3)のグリオキシム誘導体、
iv.下記一般式(P4)のビススルホン誘導体、
v.下記一般式(P5)のN−ヒドロキシイミド化合物のスルホン酸エステル、
vi.β−ケトスルホン酸誘導体、
vii.ジスルホン誘導体、
viii.ニトロベンジルスルホネート誘導体、
ix.スルホン酸エステル誘導体
等が挙げられる。
下記一般式(A1)〜(A10)で示される化合物のフェノール性水酸基の水素原子の一部又は全部を−R401−COOH(R401は炭素数1〜10の直鎖状又は分岐状のアルキレン基)により置換してなり、かつ分子中のフェノール性水酸基(C)と≡C−COOHで示される基(D)とのモル比率がC/(C+D)=0.1〜1.0である化合物。
下記一般式(A11)〜(A15)で示される化合物。
なお、ここで得られた重合体の物性値は、以下の方法により測定した。
500mlのオートクレーブに環状オレフィン単量体として8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(27.04g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(13.69g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(7.21g)をテトラヒドロフラン(以後THFと言う)250mlに溶解した。これに1,5−ヘキサジエン(1.47g)、重合触媒としてMo(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)2Me)2(343mg)を加えて50℃で1時間反応させた。その後、ブチルアルデヒド(100mg)を加え30分間攪拌し、反応を停止させた。
この開環メタセシス重合体溶液をメタノール中に加えて開環メタセシス重合体を析出させ、濾過、メタノール洗浄し、真空乾燥して46.8gの開環メタセシス重合体粉末を得た。
得られた開環メタセシス重合体水素添加物の1H−NMRスペクトルを図1に示す。
実施例1において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(20.22g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(17.02g)、ビシクロ[2.2.1]ヘプト−2−エン(4.20g)、1−オクテン(1.23g)に代えた以外は実施例1と同様に開環メタセシス重合を行い、40.4gの開環メタセシス重合体粉末を得た。
実施例1において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(13.52g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(17.04g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン、(10.73g)、1,6−ヘプタジエン(0.92g)、および重合触媒をW(N−2,6−Me2C6H3)(CHCMe2Ph)(OC(CF3)2Me)2(357mg)に代え、50℃で2時間反応させた以外は実施例1と同様に開環メタセシス重合を行い、40.01gの開環メタセシス重合体を得た。
窒素下で300mlのシュレンクフラスコに環状オレフィンモノマーとして8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(3.61g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(3.04g)、ヘキサシクロ[6.6.1.02,7.09,14.13,6.110,13]−4−ヘプタラデセン(1.81g)をTHF150mlに溶解した。これに開環メタセシス重合触蝶としてW(N−2,6−Me2C6H3)(CHCMe2Ph)(OC(CF3)2Me)2(2.00g)を加え室温で3時間反応させた。その後、ブチルアルデヒド(500mg)を加え30分間撹件し、反応を停止させた。
この開環メタセシス重合体溶液をメタノール中に加えて開環メタセシス重合体を析出させ、濾過、メタノール洗浄し、真空乾燥して8.0gの開環メタセシス重合体粉末を得た。
実施例4において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(3.61g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(3.04g)、テトラシクロ[4.3.0.12,5]−3−ノネン(1.07g)、および重合触媒をMo(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)3)2(1.06g)に代えた以外は実施例4と同様に開環メタセシス重合を行い7.3gの開環メタセシス重合体を得た。
実施例4において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(3.61g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(3.04g)、ペンタシクロ[7.4.4.0.32,5.37,13]−3−ペンタデセン(1.60g)、および重合触媒をMo(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)3)2(1.17g)に代えた以外は実施例4と同様に開環メタセシス重合を行い7.8gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(20.13g)、スピロ[ジヒドロフラン−3(2H),2'−[7]オキサビシクロ[2.2.1]ヘプタ−5−エン]−2−オン(18.69g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(7.21g)、1,5−ヘキサジエン(0.64g)、重合触媒をMo(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)2Me)2(343mg)に代えた以外は実施例1と同様に開環メタセシス重合を行い、44.3gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(20.13g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(10.19g)、4−オキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(6.76g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(7.21g)、1,6−ヘプタジエン(1.46g)、および重合触媒をW(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)3)2(431mg)に代え、50℃で2時間反応させた以外は実施例1と同様に開環メタセシス重合を行い、43.3gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(20.13g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(10.19g)、4−オキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(6.76g)、テトラシクロ[4.3.0.12,5]−3−ノネン(6.04g)、1,6−ヘプタジエン(1.59g)、および重合触媒をW(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)3)2(431mg)に代え、50℃で2時間反応させた以外は実施例1と同様に開環メタセシス重合を行い43.1gの開環メタセシス重合体を得た。
実施例4において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(3.61g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(1.83g)、スピロ[ジヒドロフラン−3(2H),2'−オキサビシクロ[2.2.1]ヘプタ−5−エン]−2−オン(1.31g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(1.28g)、および重合触媒をRu(P(C6H11)3)2(CHPh)Cl2(981mg)に代えた以外は実施例4と同様に開環メタセシス重合を行い、7.63gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−(1'−メチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(19.25g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(17.04g)、テトラシクロ[4.3.0.12,5]−3−ノネン(6.04g)、1−オクテン(1.24g)、および重合触媒をW(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)3)2(431mg)に代え、50℃で2時間反応させた以外は実施例1と同様に開環メタセシス重合を行い、41.3gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−tert−ブチルオキシカルボニル−テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(17.50g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(17.04g)、テトラシクロ[4.3.0.12,5]−3−ノネン(6.04g)、1,5−ヘキサジエン(1.29g)、および重合触媒をMo(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)Me2)2(295mg)に代えた以外は実施例1と同様に開環メタセシス重合を行い、39.7gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−(1'−メチル−1'−エチル−プロピルオキシカルボニル)−テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(19.32g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(17.04g)、テトラシクロ[4.3.0.12,5]−3−ノネン(6.04g)、1,5−ヘキサジエン(1.55g)、および重合触媒をMo(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)2Me)2(343mg)に代えた以外は実施例1と同様に開環メタセシス重合を行い、41.6gの開環メタセシス重合体を得た。
実施例4において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(4.81g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(2.43g)、テトラシクロ[4.3.0.12,5]−3−ノネン(1.07g)、および重合触媒をMo(N−2,6−Me2C6H3)(CHCMe2Ph)(OC(CF3)Me2)2(1.20g)に代えた以外は実施例4と同様に開環メタセシス重合を行い、7.9gの開環メタセシス重合体を得た。
実施例14において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(4.81g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(2.43g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン、(1.28g)、および重合触媒をMo(N−2,6−Me2C6H3)(CHCMe2Ph)(OC(CF3)Me2)2(925mg)に代えた以外は実施例14と同様に開環メタセシス重合を行い、8.1gの開環メタセシス重合体を得た。
実施例14において環状オレフィン単量体を8−(2'−エチルビシクロ[2.2.1]ヘプチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(5.22g)、4,10−ジオキサ−5,5−ジメチルトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(2.28g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン、(1.28g)、および重合触媒をRu(P(C6H11)3)2(CHPh)Cl2(1.15g)に代え室温で3時間反応させた以外は実施例14と同様に開環メタセシス重合を行い8.3gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を5−(1'−エチル−シクロペンチルオキシカルボニル)−ビシクロ[2.2.1]ヘプト−2−エン(21.00g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(13.69g)、テトラシクロ[4.3.0.12,5]−3−ノネン(6.04g)、1,5−ヘキサジエン(0.71g)、および重合触媒をMo(N−2,6−iPr2C6H3)(CHCMe2Ph)(OCMe3)2(246mg)に代えた以外は実施例1と同様に開環メタセシス重合を行い、39.3gの開環メタセシス重合体を得た。
実施例17において環状オレフィン単量体を5−(1'−エチル−シクロペンチルオキシカルボニル)−ビシクロ[2.2.1]ヘプト−2−エン(21.00g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(13.69g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン、(7.21g)、1,5−ヘキサジエン(0.70g)、および重合触媒をW(N−2,6−iPr2C6H3)(CHCMe2Ph)(OCMe3)2(286mg)に代え50℃で2時間反応させた以外は実施例17と同様に開環メタセシス重合を行い40.4gの開環メタセシス重合体を得た。
実施例14において環状オレフィン単量体を8−(1'−メチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(3.44g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(2.43g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン、(1.28g)、および重合触媒をRu(P(C6H11)3)2(CHPh)Cl2(934mg)に代えた以外は実施例14と同様に開環メタセシス重合を行い、6.79gの開環メタセシス重合体を得た。
実施例14において環状オレフィン単量体を8−(1'、1'−ジメチル−プロピルオキシカルボニル)−テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(3.29g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(2.43g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(1.28g)、および重合触媒をRu(P(C6H11)3)2(CHPh)Cl2(1.03g)に代えた以外は実施例14と同様に開環メタセシス重合を行い、6.65gの開環メタセシス重合体を得た。
実施例4において環状オレフィン単量体を5−(1'−エチル−シクロペンチルオキシカルボニル)−ビシクロ[2.2.1]ヘプト−2−エン(1.87g)、8−tert−ブチルオキシカルボニル−テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(2.08g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(2.43g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン、(1.28g)および重合触媒をRu(P(C6H11)3)2(CHPh)Cl2(456mg)に代えた以外は実施例4と同様に開環メタセシス重合を行い、7.28gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(13.52g)、5−(1'−エチル−シクロペンチルオキシカルボニル)−7−オキシビシクロ[2.2.1]ヘプト−2−エン(16.07g)、4−オキシトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(10.21g)、テトラシクロ[4.3.0.12,5]−3−ノネン(6.04g)、1,6−ヘプタジエン(0.80g)、および重合触媒をW(N−2,6−Me2C6H3)(CHCMe2Ph)(OC(CF3)2Me)2(357mg)に代え50℃で2時間反応させた以外は実施例1と同様に開環メタセシス重合を行い、44.2gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8−(1'−エチル−シクロペンチルオキシカルボキシメチル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(21.38g)、4,10−ジオキサトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(20.54g)、テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(3.69g)、1,6−ヘプタジエン(2.15g)、および重合触媒をW(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)3)2(431mg)に代え50℃で2時間反応させた以外は実施例1と同様に開環メタセシス重合を行い、45.6gの開環メタセシス重合体を得た。
実施例1において環状オレフィン単量体を8,9−ジ(1'−エチル−シクロペンチルオキシカルボニル)テトラシクロ[4.4.0.12,5.17,10]−3−ドデセン(29.96g)、4,10−ジオキサ−5,5−ジメチルトリシクロ[5.2.1.02,6]デカ−8−エン−3−オン(24.33g)、テトラシクロ[4.3.0.12,5]−3−ノネン(3.09g)、1,6−ヘプタジエン(1.23g)、および重合触媒をW(N−2,6−iPr2C6H3)(CHCMe2Ph)(OC(CF3)3)2(431mg)に代え50℃で2時間反応させた以外は実施例1と同様に開環メタセシス重合を行い、56.2gの開環メタセシス重合体を得た。
本発明の高分子化合物について、ベース樹脂としてレジスト材料に配合した際の解像性の評価、及び耐エッチング性の評価を行った。
上記式で示されるポリマー(Polymer1〜24)及び比較として下記式で示されるポリマー(Polymer25〜32)をベース樹脂とし、酸発生剤、塩基性化合物、及び溶剤を、表1に示す組成で混合した。次にそれらをテフロン(登録商標)製フィルター(孔径0.2μm)で濾過し、レジスト材料とした。
TPSNf:ノナフルオロブタンスルホン酸トリフェニルスルホニウム
TMMEA:トリスメトキシメトキシエチルアミン
CyHO:シクロヘキサノン
Claims (10)
- 少なくとも下記一般式[1]
で表される構造単位[A]と、下記一般式[3]及び/又は[4]
から選ばれる構造単位[B]と、下記一般式[5]及び/又は[6]
から選ばれる構造単位[C]とから構成され、かつ、構造単位[A]の一般式[1]のX1、構造単位[B]の一般式[3]のX2、及び一般式[4]のX3のうち少なくとも1つが−O−であり、その構成モル比が[A]/([B]+[C])=20/80〜98/2、([A]+[B])/[C]=99/1〜50/50、([A]+[C])/[B]=99/1〜21/79を同時に満たす開環メタセシス重合体水素添加物。 - 一般式[1]のR1〜R4のうち少なくとも一つとして選ばれる一般式[2]中のR6が、1−アルキルシクロペンチル基、2−アルキル−2−ノルボルニル基又は2−アルキル−2−アダマンチル基である請求項1に記載の開環メタセシス重合体水素添加物。
- 一般式[7]
で表される構造単位[D]を更に含む請求項1または2に記載の開環メタセシス重合体水素添加物。 - 一般式[1]で表される構造単位[A]、一般式[3]及び/又は[4]で表される構造単位[B]、一般式[5]及び/又は[6]で表される構造単位[C]の合計と、一般式[7]で表される構造単位[D]との構成モル比が([A]+[B]+[C])/[D]=100/0〜20/80である請求項3に記載の開環メタセシス重合体水素添加物。
- 一般式[9]
で表される構造単位[E]を更に含む請求項1ないし4のいずれかに記載の開環メタセシス重合体水素添加物。 - 一般式[1]で表される構造単位[A]、一般式[3]及び/又は[4]で表される構造単位[B]、一般式[5]及び/又は[6]で表される構造単位[C]の合計と、一般式[9]で表される構造単位[E]との構成モル比が([A]+[B]+[C])/[E]=100/0〜40/60である請求項5に記載の開環メタセシス重合体水素添加物。
- 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数平均分子量が2,000〜200,000である請求項1ないし6のいずれかに記載の開環メタセシス重合体水素添加物。
- GPCで測定したポリスチレン換算の数平均分子量が3,000〜50,000である請求項7に記載の開環メタセシス重合体水素添加物。
- 請求項1ないし8のいずれかに記載の開環メタセシス重合体水素添加物をベース樹脂として含有するレジスト材料。
- 請求項1ないし8のいずれかに記載の開環メタセシス重合体水素添加物をベース樹脂として含有するレジスト材料を基板上に塗布する工程と、加熱処理後フォトマスクを介して高エネルギー線もしくは電子線で露光する工程と、必要に応じて加熱処理した後、現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
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- 2007-09-27 KR KR1020070097339A patent/KR100905363B1/ko active IP Right Grant
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TWI386427B (zh) | 2013-02-21 |
TW200815495A (en) | 2008-04-01 |
KR20080030500A (ko) | 2008-04-04 |
US7794915B2 (en) | 2010-09-14 |
KR100905363B1 (ko) | 2009-07-01 |
US20080085470A1 (en) | 2008-04-10 |
JP2008081633A (ja) | 2008-04-10 |
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