JP5256953B2 - 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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- JP5256953B2 JP5256953B2 JP2008235209A JP2008235209A JP5256953B2 JP 5256953 B2 JP5256953 B2 JP 5256953B2 JP 2008235209 A JP2008235209 A JP 2008235209A JP 2008235209 A JP2008235209 A JP 2008235209A JP 5256953 B2 JP5256953 B2 JP 5256953B2
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- BQTNXOJCCVWLCN-UHFFFAOYSA-M diphenyl-(2,4,6-trimethylphenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC1=CC(C)=CC(C)=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 BQTNXOJCCVWLCN-UHFFFAOYSA-M 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- FDXCBBBNMIJMLF-UHFFFAOYSA-M diphenyliodanium;octane-1-sulfonate Chemical compound CCCCCCCCS([O-])(=O)=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 FDXCBBBNMIJMLF-UHFFFAOYSA-M 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- QSVAYRBPFFOQMK-UHFFFAOYSA-N ditert-butyl hexanedioate Chemical compound CC(C)(C)OC(=O)CCCCC(=O)OC(C)(C)C QSVAYRBPFFOQMK-UHFFFAOYSA-N 0.000 description 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XMWSUKJNPRAXAU-UHFFFAOYSA-N fluoro benzenesulfonate Chemical compound FOS(=O)(=O)C1=CC=CC=C1 XMWSUKJNPRAXAU-UHFFFAOYSA-N 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000004031 fumaroyl group Chemical group C(\C=C\C(=O)*)(=O)* 0.000 description 1
- 229940100608 glycol distearate Drugs 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- 125000003651 hexanedioyl group Chemical group C(CCCCC(=O)*)(=O)* 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
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- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- CNMFHDIDIMZHKY-UHFFFAOYSA-N methyl 2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)C CNMFHDIDIMZHKY-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 1
- HEPOEAALKWFVLE-UHFFFAOYSA-N n -((perfluorooctanesulfonyl)oxy)-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C1=O HEPOEAALKWFVLE-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
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- POVITWJTUUJBNK-UHFFFAOYSA-N n-(4-hydroxyphenyl)prop-2-enamide Chemical compound OC1=CC=C(NC(=O)C=C)C=C1 POVITWJTUUJBNK-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- LABYRQOOPPZWDG-UHFFFAOYSA-M naphthalene-1-sulfonate;triphenylsulfanium Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 LABYRQOOPPZWDG-UHFFFAOYSA-M 0.000 description 1
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- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000005485 noradamantyl group Chemical group 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- AUBNVERMHFAAKM-UHFFFAOYSA-M octane-1-sulfonate;triphenylsulfanium Chemical compound CCCCCCCCS([O-])(=O)=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 AUBNVERMHFAAKM-UHFFFAOYSA-M 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([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 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 1
- 125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003220 pyrenes 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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- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 1
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- 230000005469 synchrotron radiation Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- MAOCPIDAEMTJLK-UHFFFAOYSA-N tris(4-fluorophenyl)sulfanium Chemical compound C1=CC(F)=CC=C1[S+](C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 MAOCPIDAEMTJLK-UHFFFAOYSA-N 0.000 description 1
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
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- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Description
[2]前記感光性塩基性化合物(C)が、下記一般式(9−1)又は(9−2)で表される化合物である前記[1]に記載の感放射線性組成物。
[5]前記露光が、電子線、EUV又はX線による露光である前記[3]又は[4]に記載のパターン形成方法。
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は、感光性塩基性化合物(C)を含有するものである。感光性塩基性化合物(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。このような感光性塩基性化合物(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)及び感光性塩基性化合物(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2〜4、参考例1〜2、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 (5)
- 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)と、感光性塩基性化合物(C)と、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って、下記(iii)で表される繰り返し単位の割合が、重合体(A)に含まれる全ての繰り返し単位の合計を100mol%とした場合に、20〜40mol%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又は2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3に記載のパターン形成方法。
- 前記露光が、電子線、EUV又はX線による露光である請求項3又は4に記載のパターン形成方法。
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