JP4049762B2 - レジスト用重合体の製造方法 - Google Patents
レジスト用重合体の製造方法 Download PDFInfo
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- JP4049762B2 JP4049762B2 JP2004139853A JP2004139853A JP4049762B2 JP 4049762 B2 JP4049762 B2 JP 4049762B2 JP 2004139853 A JP2004139853 A JP 2004139853A JP 2004139853 A JP2004139853 A JP 2004139853A JP 4049762 B2 JP4049762 B2 JP 4049762B2
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- 229920000642 polymer Polymers 0.000 title claims description 277
- 238000004519 manufacturing process Methods 0.000 title claims description 35
- 239000002904 solvent Substances 0.000 claims description 153
- 239000000178 monomer Substances 0.000 claims description 120
- 238000001226 reprecipitation Methods 0.000 claims description 87
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- 238000006116 polymerization reaction Methods 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 113
- 125000004432 carbon atom Chemical group C* 0.000 description 98
- 238000006243 chemical reaction Methods 0.000 description 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 52
- 238000003756 stirring Methods 0.000 description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
- 125000000217 alkyl group Chemical group 0.000 description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 31
- 239000000203 mixture Substances 0.000 description 31
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- UJKWLAZYSLJTKA-UHFFFAOYSA-N edma Chemical compound O1CCOC2=CC(CC(C)NC)=CC=C21 UJKWLAZYSLJTKA-UHFFFAOYSA-N 0.000 description 22
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- 125000003277 amino group Chemical group 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 15
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- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
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- 125000002723 alicyclic group Chemical group 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 150000001875 compounds Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- 125000006823 (C1-C6) acyl group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- LYGKSUOGJYYSOI-UHFFFAOYSA-N 2-methoxybuta-1,3-diene Chemical compound COC(=C)C=C LYGKSUOGJYYSOI-UHFFFAOYSA-N 0.000 description 2
- XJLDYKIEURAVBW-UHFFFAOYSA-N 3-decanone Chemical compound CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- 238000007259 addition reaction Methods 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
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Description
水とメタノールからなる再沈殿溶媒に前記重合体を含む溶液を滴下し、滴下終了時の全溶媒のSP値が30〜35[MPa1/2]である再沈殿工程と
を有するレジスト用重合体の製造方法に関する。
混合溶媒のSP値=(溶媒AのSP値×溶媒Aのモル比+溶媒BのSP値×溶媒Bのモル比+・・)
のようにして算出する。すなわち、
混合溶媒のSP値=Σ(混合溶媒を構成する成分iのSP値×混合溶媒中の成分i
のモル分率)
とする。
Re=nd2ρ/μ
(式中、nは攪拌翼の回転数[s-1]、dは攪拌翼径[m]、ρは液体の密度[kg・m-3]、μは液体の粘度[Pa・s]を表す。)
で定義される無次元数である。
ここで、乾燥後の質量とは、溶剤を含んでいる当該レジスト用重合体を0.1torrの減圧下、80℃で36時間以上真空乾燥した後の質量をいう。
なお、式(3−1−1)、式(3−2−1)および式(3−3−1)において、X1、X2およびX3で置換される位置は、環状構造のどの位置であってもよい。
酸脱離性基を有する構成単位を重合体に導入するためには、酸脱離性基を有する単量体を重合(共重合も含む)すればよい。酸脱離性基を有する単量体は、1種、あるいは、必要に応じて2種以上を組み合わせて使用することができる。
なお、式(4−1)、式(4−2)、式(4−3)、式(4−4)、式(4−5)および式(4−6)において、X5、X6、X7、X8、X9およびX10で置換される位置は、環状構造のどの位置であってもよい。
前記式(1)で表される構成単位を重合体に導入するためには、下記式(5)で表されるシアノ基を有する(メタ)アクリル酸エステル誘導体を含むモノマー組成物を共重合すればよい。下記式(5)で表される(メタ)アクリル酸エステル誘導体は、1種、あるいは、必要に応じて2種以上を組み合わせて使用することができる。
なお、「(メタ)アクリル酸」は、アクリル酸とメタクリル酸の総称である。
前記式(1−1)で表される構成単位を重合体に導入するためには、下記式(5−1)で表されるシアノ基を有する(メタ)アクリル酸エステル誘導体を含むモノマー組成物を共重合すればよい。下記式(5−1)で表される(メタ)アクリル酸エステル誘導体は、1種、あるいは、必要に応じて2種以上を組み合わせて使用することができる。
式(5−1)中、R03は水素原子または炭素数1〜6の直鎖もしくは分岐アルキル基を表す。R03としては、他の単量体との共重合性に優れる点から、エチル基、メチル基、水素原子が好ましく、メチル基がより好ましい。
マレイン酸、無水マレイン酸、イタコン酸、無水イタコン酸等の不飽和カルボン酸およびカルボン酸無水物;
エチレン、プロピレン、ノルボルネン、テトラフルオロエチレン、アクリルアミド、N−メチルアクリルアミド、N,N−ジメチルアクリルアミド、塩化ビニル、エチレン、フッ化ビニル、フッ化ビニリデン、テトラフルオロエチレン、ビニルピロリドン等
が挙げられる。これらの単量体は、必要に応じて1種または2種以上を組み合わせて使用することができる。
反応装置として、羽径13cmの平羽根を設置した3Lの反応釜を使用した。
再沈殿溶媒をメタノール1900gとした以外は実施例1と同様にして重合反応、再沈殿を行い、重合体80gを得た。再沈殿溶媒のSP値は29.7[MPa1/2]である。再沈殿工程において、反応液の滴下完了時の溶液のSP値は28.5であり、また、反応液の滴下開始時の再沈殿溶媒の攪拌レイノルズ数(Re)は63000であった。また、再沈殿工程において、反応液の滴下終了後、攪拌を続けていたところ、徐々にスラリー物が塊状になっていくのが確認された。この塊状物は、塊状になった後、攪拌数を700rpmまで上げても元の状態には戻らなかった。
反応装置として、羽径13cmの平羽根を設置した3Lの反応釜を使用した。
再沈殿溶媒をメタノール1000gおよび水333gの混合溶液とした以外は実施例2と同様にして重合反応、再沈殿を行い、重合体160gを得た。再沈殿溶媒のSP値は36.5[MPa1/2]である。再沈殿工程において、反応液の滴下完了時の溶液のSP値は35.6であった。
Claims (6)
- 重合することにより目的とする重合体の構成単位となる単量体を溶剤中で溶液重合して、目的とする重合体を含む溶液を得る重合工程と、
水とメタノールからなる再沈殿溶媒に前記重合体を含む溶液を滴下し、滴下終了時の全溶媒のSP値が30〜35[MPa1/2]である再沈殿工程と
を有するレジスト用重合体の製造方法。 - 前記再沈殿工程において、前記重合体を含む溶液の滴下開始時に、前記反応器内の再沈殿溶媒が、攪拌レイノルズ数が1000〜1000000の範囲になるように攪拌されている請求項1に記載のレジスト用重合体の製造方法。
- 製造される重合体が、親水性基を有する構成単位を含有するレジスト用重合体である請求項1または2に記載のレジスト用重合体の製造方法。
- 製造される重合体が、酸脱離性基を有する構成単位と、ラクトン骨格を有する構成単位とを含有する化学増幅型レジスト用重合体である請求項1または2に記載のレジスト用重合体の製造方法。
- 製造される重合体が、親水性基を有する構成単位を含有する請求項4に記載のレジスト
用重合体の製造方法。 - 製造される重合体が、シアノ基を有する構成単位を含有する請求項4に記載のレジスト
用重合体の製造方法。
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