JP2016044157A - N−アシルカルバモイル基及びラクトン骨格を含む単量体、及び高分子化合物 - Google Patents
N−アシルカルバモイル基及びラクトン骨格を含む単量体、及び高分子化合物 Download PDFInfo
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- JP2016044157A JP2016044157A JP2014171090A JP2014171090A JP2016044157A JP 2016044157 A JP2016044157 A JP 2016044157A JP 2014171090 A JP2014171090 A JP 2014171090A JP 2014171090 A JP2014171090 A JP 2014171090A JP 2016044157 A JP2016044157 A JP 2016044157A
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- 239000000178 monomer Substances 0.000 title claims abstract description 144
- 229920000642 polymer Polymers 0.000 title claims abstract description 74
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- 125000000686 lactone group Chemical group 0.000 title claims abstract description 7
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- 125000005843 halogen group Chemical group 0.000 claims abstract description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 40
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
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- 239000007788 liquid Substances 0.000 description 8
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- 239000002585 base Substances 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 238000011161 development Methods 0.000 description 7
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- 239000003505 polymerization initiator Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- WLZMKZGLQVILBX-UHFFFAOYSA-N 2-(1-adamantyl)propan-2-yl 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(C(C)(C)OC(=O)C(=C)C)C3 WLZMKZGLQVILBX-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 239000003377 acid catalyst Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
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- MZVABYGYVXBZDP-UHFFFAOYSA-N 1-adamantyl 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C(=C)C)C3 MZVABYGYVXBZDP-UHFFFAOYSA-N 0.000 description 5
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- WKOARXCZOFTJEB-UHFFFAOYSA-N hexahydro-2h-3,5-methanocyclopenta[b]furan Chemical group C1C2COC3C2CC1C3 WKOARXCZOFTJEB-UHFFFAOYSA-N 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 125000002347 octyl 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])[H] 0.000 description 5
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000003997 cyclic ketones Chemical group 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 1
- GRCAXSKSTZXYIK-UHFFFAOYSA-N cyclopentanecarbonyl cyclopentanecarboxylate Chemical compound C1CCCC1C(=O)OC(=O)C1CCCC1 GRCAXSKSTZXYIK-UHFFFAOYSA-N 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000002792 delta-lactamyl group Chemical group 0.000 description 1
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- BLZKAXUWWPHZCN-UHFFFAOYSA-N dodecane-5,8-dione Chemical compound CCCCC(=O)CCC(=O)CCCC BLZKAXUWWPHZCN-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000001965 gamma-lactamyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OCUXHFVNHQTZKR-UHFFFAOYSA-M methanesulfonate;triphenylsulfanium Chemical compound CS([O-])(=O)=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 OCUXHFVNHQTZKR-UHFFFAOYSA-M 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- CMUWMQXDTPDEDU-UHFFFAOYSA-N tert-butyl 5-oxo-1-prop-2-enoyloxy-4-oxatricyclo[4.2.1.03,7]nonane-9-carboxylate Chemical compound C(C=C)(=O)OC12CC3OC(C(C3C1)C2C(=O)OC(C)(C)C)=O CMUWMQXDTPDEDU-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Furan Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
【解決手段】下記式(1)で表されるN−アシルカルバモイル基及びラクトン骨格を含む単量体。
(Raは水素原子、炭素数1〜6のアルキル基等;R1はハロゲン原子、ハロゲン原子を有していてもよい炭素数1〜6のアルキル基等を示す。Aは炭素数1〜6のアルキレン基、O、S又は非結合;mは0〜8の整数;Xは特定のN−アシルカルバモイル基;nは1〜9の整数;Yは炭素数1〜6の2価の有機基)
【選択図】なし
Description
で表されるN−アシルカルバモイル基を示す。nは環に結合しているXの個数であって1〜9の整数を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表されるN−アシルカルバモイル基及びラクトン骨格を含む単量体を提供する。
で表されるN−アシルカルバモイル基を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表される化合物が含まれる。
で表されるN−アシルカルバモイル基を示す。nは環に結合しているXの個数であって1〜9の整数を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表されるモノマー単位を少なくとも有する高分子化合物を提供する。
で表されるN−アシルカルバモイル基を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表されるモノマー単位が含まれる。
から選ばれるモノマー単位であってもよい。
から選ばれるモノマー単位が含まれる。
本発明のN−アシルカルバモイル基及びラクトン骨格を含む単量体(化合物)(6−オキサビシクロ[3.2.11,5]オクタン−7−オン誘導体及び3−オキサトリシクロ[4.2.1.04,8]ノナン−2−オン誘導体等)は前記式(1)で表される。式(1)中、Raは水素原子、ハロゲン原子、又は置換基を有していてもよい炭素数1〜6のアルキル基を示し、R1は環[6−オキサビシクロ[3.2.11,5]オクタン環(Aが非結合の場合)、3−オキサトリシクロ[4.2.1.04,8]ノナン環(Aがメチレン基の場合)等]に結合している置換基であって、ハロゲン原子、ハロゲン原子を有していてもよい炭素数1〜6のアルキル基、ヒドロキシル基部分が保護基で保護されていてもよく且つハロゲン原子を有していてもよい炭素数1〜6のヒドロキシアルキル基、塩を形成していてもよいカルボキシル基、又は置換オキシカルボニル基を示す。Aは炭素数1〜6のアルキレン基、酸素原子、硫黄原子又は非結合を示す。mはR1の個数であって0〜8の整数を示す。Xは前記式(2)で表されるN−アシルカルバモイル基を示す。nは環[6−オキサビシクロ[3.2.11,5]オクタン環(Aが非結合の場合)、3−オキサトリシクロ[4.2.1.04,8]ノナン環(Aがメチレン基の場合)等]に結合しているXの個数であって1〜9の整数を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい。
で表されるシアノ基及びラクトン骨格を有する化合物に、酸の存在下、下記式(7)
(Rb−CO)2O (7)
(式中、Rbは前記に同じ)
で表される酸無水物を反応させ、次いで加水分解する。この方法により、式(1)において、Xが−CO−NH−CORbである化合物が得られる。
で表されるカルバモイル基及びラクトン骨格を有する化合物を得、この化合物に、下記式(8)
Rb−COZ (8)
(式中、Rbは前記に同じ。Zはハロゲン原子を示す)
で表される酸ハロゲン化物を反応させる。この方法により、式(1)において、Xが−CO−NH−CORbである化合物が得られる。
RcOH (9)
[Rcは前記に同じ(但し、水素原子を除く)]
で表されるアルコールと反応させて、下記式(4b)
で表されるN−アルキル置換カルバモイル基及びラクトン骨格を有する化合物を得、この化合物に、前記式(8)で表される酸ハロゲン化物を反応させる。この方法により、式(1)において、Xが−CO−NRc−CORbである化合物が得られる。
本発明の高分子化合物は上記式(1)で表されるN−アシルカルバモイル基及びラクトン骨格を含む単量体に対応する(由来する)モノマー単位(繰り返し単位)、すなわち前記式(I)で表されるモノマー単位を含んでいる。該モノマー単位は1種又は2種以上含んでいてもよい。このような高分子化合物は、上記式(1)で表されるN−アシルカルバモイル基及びラクトン骨格を含む単量体を重合に付すことにより得ることができる。
高分子化合物の重量平均分子量(Mw)は、例えば1000〜500000程度、好ましくは3000〜50000程度であり、分子量分布(Mw/Mn)は、例えば1.5〜2.5程度である。なお、前記Mnは数平均分子量を示し、Mn、Mwともにポリスチレン換算の値である。
1H−NMR(DMSO−d6)δ:7.58(1H,brs),7.37(1H,brs),6.07(1H,s),5.72(1H,s),4.65(1H,d),4.56(1H,s),3.48(1H,d),2.51−2.54(1H,m),2.44(1H,dd),1.92(1H,d),1.89(3H,s),1.76(1H,dd),1.59(1H,d)
1H−NMR(CDCl3)δ:9.72(1H,brs),6.12(1H,m),5.64(1H,m),4.67(1H,m),4.65(1H,m),3.49(1H,m),2.70(1H,m),2.42(3H,s),2.29−2.33(1H,m),2.09−2.15(3H,m),1.95(3H,s)
1H−NMR(CDCl3)δ:9.68(1H,brs),6.23(1H,m),5.69(1H,m),4.62−4.70(4H,m),3.48(1H,m),2.69(1H,m),2.42(3H,s),2.28−2.32(1H,m),2.05−2.15(3H,m),1.99(3H,s)
下記構造の高分子化合物(共重合体)の合成
実施例9
下記構造の高分子化合物(共重合体)の合成
実施例及び比較例で得られた各フォトレジスト用ポリマー樹脂にプロピレングリコールモノメチルエーテルアセテート(PGMEA)を添加して、ポリマー濃度20重量%のPGMEA溶液となるように、樹脂を溶解した。得られた各フォトレジスト用ポリマー溶液に、ポリマー100重量部に対して10重量部のトリフェニルスルホニウムヘキサフルオロアンチモネートを加え、さらにPGMEAを加えてポリマー濃度15重量% に調整し、孔径0.02μmのフィルターで濾過することによりフォトレジスト組成物を調製した。
このフォトレジスト組成物をシリコンウエハーにスピンコーティング法により塗布し、厚み0.7μmの感光層を形成した。ホットプレート上で温度100℃で150秒間プリベークした後、波長193nmのArFエキシマレーザーを用い、マスクを介して、照射量30mJ/cm2で露光した後、100℃の温度で60秒間ポストベークした。次いで、2.38Mのテトラメチルアンモニウムヒドロキシド水溶液により60秒間現像し、超純水でリンスした。実施例及び比較例の何れのフォトレジスト用ポリマー溶液を用いた場合にも、0.25μmのライン・アンド・スペースパターンは得られたが、実施例は比較例と比べ明らかに鮮明でかつ欠陥が少なかった。
Claims (10)
- 下記式(1)
で表されるN−アシルカルバモイル基を示す。nは環に結合しているXの個数であって1〜9の整数を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表されるN−アシルカルバモイル基及びラクトン骨格を含む単量体。 - 下記式(1a)
で表されるN−アシルカルバモイル基を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表される化合物である請求項1記載のN−アシルカルバモイル基及びラクトン骨格を含む単量体。 - 下記式(I)
で表されるN−アシルカルバモイル基を示す。nは環に結合しているXの個数であって1〜9の整数を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表されるモノマー単位を少なくとも有する高分子化合物。 - 前記式(I)で表されるモノマー単位が、下記式(Ia)
で表されるN−アシルカルバモイル基を示す。Yは炭素数1〜6の2価の有機基を示す。kは0又は1を示す。CH2=C(Ra)CO−(O−Y−CO)k−O−基の立体的な位置はエンド、エキソの何れであってもよい]
で表されるモノマー単位である請求項3記載の高分子化合物。 - 式(I)で表されるモノマー単位に加えて、さらに、酸の作用により脱離してアルカリ可溶となるモノマー単位を少なくとも有する請求項3又は4記載の高分子化合物。
- 酸の作用により脱離してアルカリ可溶となるモノマー単位が、下記式(Va)〜(Vd)
から選ばれるモノマー単位である請求項5記載の高分子化合物。 - 式(I)で表されるモノマー単位に加えて、さらに、少なくとも1つの置換基を有する脂環式骨格を含有するモノマー単位を少なくとも有する請求項3〜6の何れかの項に記載の高分子化合物。
- 少なくとも1つの置換基を有する脂環式骨格を含有するモノマー単位が、下記式(VI)
から選ばれるモノマー単位である請求項7記載の高分子化合物。 - 式(I)で表されるモノマー単位と、酸の作用により脱離してアルカリ可溶となるモノマー単位と、ヒドロキシル基及びヒドロキシメチル基から選択された置換基を少なくとも1つ有する脂環式骨格を含有するモノマー単位とを少なくとも有する請求項5又は6記載の高分子化合物。
- 式(I)で表されるモノマー単位に加えて、さらに、前記式(I)で表されるモノマー単位以外のラクトン骨格を有するモノマー単位を少なくとも有する請求項3〜9の何れかの項に記載の高分子化合物。
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JP2016044158A (ja) * | 2014-08-26 | 2016-04-04 | 株式会社ダイセル | N−アシルカルバモイル基及びラクトン骨格を含む化合物の製造方法 |
US10437147B2 (en) | 2016-03-31 | 2019-10-08 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method for forming resist pattern |
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