JP4397200B2 - レジスト組成物 - Google Patents
レジスト組成物 Download PDFInfo
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- JP4397200B2 JP4397200B2 JP2003325607A JP2003325607A JP4397200B2 JP 4397200 B2 JP4397200 B2 JP 4397200B2 JP 2003325607 A JP2003325607 A JP 2003325607A JP 2003325607 A JP2003325607 A JP 2003325607A JP 4397200 B2 JP4397200 B2 JP 4397200B2
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- Prior art keywords
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- acid
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- Prior art date
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 29
- 239000002253 acid Substances 0.000 claims description 68
- 229920000642 polymer Polymers 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- -1 2-methoxyethoxymethyl group Chemical group 0.000 description 218
- 125000004432 carbon atom Chemical group C* 0.000 description 43
- 125000001424 substituent group Chemical group 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 238000004090 dissolution Methods 0.000 description 20
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=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 YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 description 8
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 8
- 229960002317 succinimide Drugs 0.000 description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 8
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- LMJVDYDHTWAXDL-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-4-carboxylic acid Chemical compound C1CC2C=CC1(C(=O)O)C2 LMJVDYDHTWAXDL-UHFFFAOYSA-N 0.000 description 7
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- MFNBODQBPMDPPQ-UHFFFAOYSA-N (4-tert-butylphenyl)-diphenylsulfanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 MFNBODQBPMDPPQ-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 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 6
- RCOCMILJXXUEHU-UHFFFAOYSA-N (4-methylphenyl)-diphenylsulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 RCOCMILJXXUEHU-UHFFFAOYSA-N 0.000 description 5
- GFVFSRZJKWODDS-UHFFFAOYSA-N 2-phenylbut-1-en-1-one Chemical compound CCC(=C=O)C1=CC=CC=C1 GFVFSRZJKWODDS-UHFFFAOYSA-N 0.000 description 5
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000007514 bases Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 239000012953 triphenylsulfonium Substances 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- QVLLTVALUYGYIX-UHFFFAOYSA-N [4-[(2-methylpropan-2-yl)oxy]phenyl]-diphenylsulfanium Chemical compound C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 QVLLTVALUYGYIX-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003277 amino group Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 125000005395 methacrylic acid group Chemical group 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000005188 oxoalkyl group Chemical group 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- XNUYPROIFFCXAE-UHFFFAOYSA-N (4-cyclohexylphenyl)-diphenylsulfanium Chemical compound C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 XNUYPROIFFCXAE-UHFFFAOYSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KKDOXQYWUITYNG-UHFFFAOYSA-N 3,4-dimethylpyrrolidine-2,5-dione Chemical compound CC1C(C)C(=O)NC1=O KKDOXQYWUITYNG-UHFFFAOYSA-N 0.000 description 3
- GPIUUMROPXDNRH-UHFFFAOYSA-N 3647-74-3 Chemical compound C1C2C3C(=O)NC(=O)C3C1C=C2 GPIUUMROPXDNRH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BJUOQSZSDIHZNP-UHFFFAOYSA-N 1,4,7,10-tetraoxa-13-azacyclopentadecane Chemical compound C1COCCOCCOCCOCCN1 BJUOQSZSDIHZNP-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 2
- FVLTXCPGQRZFBQ-UHFFFAOYSA-N 1-butoxy-4-ethenylbenzene Chemical compound CCCCOC1=CC=C(C=C)C=C1 FVLTXCPGQRZFBQ-UHFFFAOYSA-N 0.000 description 2
- DTNCNFLLRLHPNJ-UHFFFAOYSA-N 1-ethenyl-4-(1-ethoxyethoxy)benzene Chemical compound CCOC(C)OC1=CC=C(C=C)C=C1 DTNCNFLLRLHPNJ-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 2
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 2
- NRTKFSQKHCMEMO-UHFFFAOYSA-N 2-(methoxymethoxy)-n,n-bis[2-(methoxymethoxy)ethyl]ethanamine Chemical compound COCOCCN(CCOCOC)CCOCOC NRTKFSQKHCMEMO-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- UCBGDYNJUOJESM-UHFFFAOYSA-N 4-ethenyl-2,3-difluorophenol Chemical compound OC1=CC=C(C=C)C(F)=C1F UCBGDYNJUOJESM-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 2
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- 239000007921 spray Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- HGPXXOYPYCIJMU-UHFFFAOYSA-N tert-butyl (3-ethenylphenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=CC(C=C)=C1 HGPXXOYPYCIJMU-UHFFFAOYSA-N 0.000 description 1
- RRFJMIZWYMSQAE-UHFFFAOYSA-N tert-butyl (4-formylphenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(C=O)C=C1 RRFJMIZWYMSQAE-UHFFFAOYSA-N 0.000 description 1
- MLJSCNMYWNQUAR-UHFFFAOYSA-N tert-butyl (4-prop-1-en-2-ylphenyl) carbonate Chemical compound CC(=C)C1=CC=C(OC(=O)OC(C)(C)C)C=C1 MLJSCNMYWNQUAR-UHFFFAOYSA-N 0.000 description 1
- AIBKTSSWLZGMLQ-UHFFFAOYSA-N tert-butyl 2-(4-ethenylphenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=C(C=C)C=C1 AIBKTSSWLZGMLQ-UHFFFAOYSA-N 0.000 description 1
- DCPZFEGEPVNZGG-UHFFFAOYSA-N tert-butyl [4-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]sulfinylphenyl] carbonate Chemical compound C1=CC(OC(=O)OC(C)(C)C)=CC=C1S(=O)C1=CC=C(OC(=O)OC(C)(C)C)C=C1 DCPZFEGEPVNZGG-UHFFFAOYSA-N 0.000 description 1
- BYOHIQHMSWKBJL-UHFFFAOYSA-N tert-butyl [4-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]sulfonylphenyl] carbonate Chemical compound C1=CC(OC(=O)OC(C)(C)C)=CC=C1S(=O)(=O)C1=CC=C(OC(=O)OC(C)(C)C)C=C1 BYOHIQHMSWKBJL-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- YUEMJCIBNHREMW-UHFFFAOYSA-N tert-butyl anthracene-9-carboxylate Chemical compound C1=CC=C2C(C(=O)OC(C)(C)C)=C(C=CC=C3)C3=CC2=C1 YUEMJCIBNHREMW-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-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
- 125000005580 triphenylene group Chemical group 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Description
(1)(A)酸との反応によりアルカリ可溶性となる重合体、(B)式(I)
(2)式(I)で表される化合物中、R1及びR2は、それぞれ独立にC1〜C20の炭化水素基、R3は、C1〜C20の炭化水素基、ヘテロ環基を表すことを特徴とする(1)に記載のレジスト組成物、
(3)式(I)で表される化合物中、R3が、式(II)
(4)式(I)で表される繰り返し単位を有する重合体の数平均分子量が、2,000〜50,000であることを特徴とする(1)〜(3)のいずれかに記載のレジスト組成物、
(5)式(I)で表される繰り返し単位を有する重合体の重量平均分子量(Mw)と数平均分子量(Mn)の比(Mw/Mn)が、1.01〜3.00の範囲であることを特徴とする(1)〜(4)のいずれかに記載のレジスト組成物、
(6)(A)酸との反応によりアルカリ可溶性となる重合体が、式(III)
(I)酸との反応によりアルカリ可溶性となる重合体
酸との反応によりアルカリ可溶性となる性質を有する重合体としては、ノボラック樹脂、フェノール樹脂、アクリル樹脂、それらの共重合体が用いられ、アルカリ溶解性を制御するために、フェノール性水酸基、またはカルボン酸等の全部または一部を酸により分解または脱離する有機基で保護して用いられるのが好ましい。特に好ましい重合体として、式(III)で表される繰り返し単位を有する重合体を例示することができる。
(II)式(I)で表される繰り返し単位を有する重合体。
メチルメタクリレート、エチルメタクリレート、プロピルメタクリレート、イソプロピルメタクリレート、アミルメタクリレート、ヘキシルメタクリレート、シクロヘキシルメタクリレート、ベンジルメタクリレート、クロルベンジルメタクリレート、オクチルメタクリレート、2−エトキシエチルメタクリレート、4−メトキシブチルメタクリレート、5−メトキシペンチルメタクリレート、2,2−ジメチル−3−エトキシプロピルメタクリレート、1−メトキシエチルメタクリレート、1−エトキシエチルメタクリレート、1−メトキシプロピルメタクリレート、1−メチル−1−メトキシエチルメタクリレート、1−(イソプロポキシ)エチルメタクリレート、フルフリルメタクリレート、テトラヒドロフルフリルメタクリレート等のメタクリル酸エステル類、クロトン酸メチル、クロトン酸エチル、クロトン酸プロピル、クロトン酸アミル、クロトン酸シクロヘキシル、クロトン酸エチルヘキシル、クロトン酸オクチル、クロトン酸−t−オクチル、クロルエチルクロトネート、2−エトキシエチルクロトネート、2,2−ジメチル−3−エトキシプロピルクロトネート、5−エトキシペンチルクロトネート、1−メトキシエチルクロトネート、1−エトキシエチルクロトネート、1−メトキシプロピルクロトネート、1−メチル−1−メトキシエチルクロトネート、1−(イソプロポキシ)エチルクロトネート、ベンジルクロトネート、メトキシベンジルクロトネート、フルフリルクロトネート、テトラヒドロフルフリルクロトネート等のクロトン酸エステル類、イタコン酸ジメチル、イタコン酸ジエチル、イタコン酸ジプロピル、イタコン酸ジアミル、イタコン酸ジシクロヘキシル、イタコン酸ビス(エチルヘキシル)、イタコン酸ジオクチル、イタコン酸−ジ−t−オクチル、ビス(クロルエチル)イタコネート、ビス(2−エトキシエチル)イタコネート、ビス(2,2−ジメチル−3−エトキシプロピル)イタコネート、ビス(5−エトキシペンチル)イタコネート、ビス(1−メトキシエチル)イタコネート、ビス(1−エトキシエチル)イタコネート、ビス(1−メトキシプロピル)イタコネート、ビス(1−メチル−1−メトキシエチル)イタコネート、ビス(1−(イソプロポキシ)エチル)イタコネート、ジベンジルイタコネート、ビス(メトキシベンジル)イタコネート、ジフルフリルイタコネート、ジテトラヒドロフルフリルイタコネート等のイタコン酸エステル類等から誘導される繰り返し単位を例示することができる。さらに、下記式で表される繰り返し単位を例示することができる。
(III)酸発生剤
本発明に用いられる酸発生剤としては、感放射線照射により酸を発生し得る化合物であってレジストパターン形成に悪影響を及ぼさないものであれば制限されないが、特に248.4 nm付近の光透過性が良好でレジスト組成物の高透明性を維持出来るか、露光により光透過性が高められレジスト組成物の高透明性を維持できるか、又は酸発生効率が高いため微量の添加で効果を発揮する酸発生剤が好ましくあげられる。特に好ましい酸発生剤としては、具体的には、下記式(XIV)、式(XV)、式(XVI)、式(XVII)、及び式(XVIII)で示される化合物等を例示することができる。
好ましい酸発生剤として具体的には、式(XIV)で示される酸発生剤としては、1−シクロヘキシルスルホニル−1−(1,1−ジメチルエチルスルホニル)ジアゾメタン、ビス(1,1−ジメチルエチルスルホニル)ジアゾメタン、ビス(1−メチルエチルスルホニル)ジアゾメタン、ビス(シクロヘキシルスルホニル)ジアゾメタン、1−シクロヘキシルスルホニル−1−シクロヘキシルカルボニルジアゾメタン、1−ジアゾ−1−シクロヘキシルスルホニル−3,3−ジメチルブタン−2−オン、1−ジアゾ−1−(1,1−ジメチルエチルスルホニル)−3,3−ジメチルブタン−2−オン等を例示することができる。
(D)有機溶剤
有機溶剤としては、(A)〜(C)成分等が溶解可能な有機溶媒であれば、特に制限されないが、具体的には、シクロヘキサノン、メチル−2−n−アミルケトン等のケトン類、3−メトキシブタノール、3−メチル−3−メトキシブタノール、1−メトキシ−2−プロパノール、1−エトキシ−2−プロパノール等のアルコール類、プロピレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル等のエーテル類、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、乳酸エチル、ピルビン酸エチル、酢酸ブチル、3−メトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、酢酸tert−ブチル、プロピオン酸tert−ブチル、プロピレングリコール−モノ−tert−ブチルエーテルアセテート等のエステル類等を例示することができ、これらの1種を単独で又は2種以上を混合して使用することができるが、これらに限定されるものではない。本発明では、これらの有機溶剤の中でもレジスト成分中の酸発生剤の溶解性が最も優れているジエチレングリコールジメチルエーテルや1−エトキシ−2−プロパノール、乳酸エチルの他、安全溶剤であるプロピレングリコールモノメチルエーテルアセテート及びその混合溶剤が好ましく使用される。
(E)塩基性化合物
塩基性化合物は、酸発生剤より発生する酸がレジスト膜中に拡散する際の拡散速度を抑制することができる化合物が適しており、このような塩基性化合物の配合により、レジスト膜中での酸の拡散速度が抑制されて解像度が向上し、露光後の感度変化を抑制したり、基板や環境依存性を少なくし、露光余裕度やパターンプロファイル等を向上することができる(特開平5−232706号、同5−249683号、同5−158239号、同5−249662号、同5−257282号、同5−289322号、同5−289340号公報等記載)。
(F)芳香族カルボン酸
本発明のレジスト組成物に分子内に≡C−COOHで示される基を有する芳香族化合物を加えることもできる。(F)成分の配合により、レジストのPED安定性を向上させ、窒化膜基板上でのエッジラフネスを改善することができる。そのような化合物として具体的には、下記式示す化合物を例示することができる。
(G)溶解制御剤
本発明のレジスト材料には、溶解速度調整用として溶解制御剤を添加することができ、これによりコントラストを向上させることができる。溶解制御剤としては、平均分子量が100〜1,000、好ましくは150〜800で、かつ分子内にフェノール性水酸基を2つ以上有する化合物の該フェノール性水酸基の水素原子を酸不安定基により全体として平均0〜100モル%の割合で置換した化合物を配合する。
(H)紫外線吸収剤
更に、本発明のレジスト材料には、紫外線吸収剤として波長248nmでのモル吸光率が10,000以下の化合物を配合することができる。これによって、反射率の異なる基板に対し、適切な透過率を有するレジストの設計・制御が可能となる。
参考例1
(1)エチルフェニルケテン(EPK)の合成
窒素雰囲気下において、トリエチルアミン 91g(0.9モル)のTHF混合液に、2−フェニルブチリルクロライド55g(0.3モル)のTHF溶液を滴下した。一時間後析出したトリエチルアミン・塩酸塩を濾過した後、濾液を減圧蒸留して、EPKを得た(60〜70℃/4mmHg)。収量 30g(収率70%)。
(2)4−(t−ブトキシカルボニルオキシ)ベンズアルデヒド(BOCBA)
窒素雰囲気下において、4−ヒドロキシベンズアルデヒド 24.4g(0.2モル)をTHF 200mlに溶解後、ジ−t−ブチルジカーボネート 52.4g(0.24モル)、N,N−ジメチルアミノピリジン 15mg(0.2ミリモル)を加え室温で一夜攪拌した。Na2CO3水溶液を加え中和後、分液し、上層をpH=7になるまで水洗した。MgSO4を加え脱水濾過後、濃縮しメタノールから再結晶してBOCBAを得た。収量35g(収率80%)。
(3)EPKとBOCBAの交互共重合
塩化リチウム 1.9g(45ミリモル)を加熱・真空乾燥後、窒素雰囲気下、THF100mlを加え、−40℃まで冷却した。更にBOCBA4.4g(32ミリモル)とEPK4.4g(30ミリモル)を添加した後、n−BuLiのヘキサン溶液 0.93ml(1.5ミリモル)を加え、−40℃で30分間反応を継続した。メタノールを加えて反応を停止した後、大量のメタノールに加えて再沈殿し、生じた沈殿を濾過、減圧乾燥することにより、白色粉末状のポリマー(a)を8.5g得た。ポリマー(a)をゲルパーミエーションクロマトグラフィー(以下、「GPC」と略す)により分析したところ、Mn=8000、Mw/Mn=1.18の単分散ポリマーであった。
参考例2
ポリ(p−ヒドロキシスチレン)[日本曹達社製VP−15000、Mn=18000、Mw/Mn=1.10]50gを窒素有雰囲気下で酢酸エチル200mlに溶解後、エチルビニルエーテル15gと濃塩酸0.3mlを加えて、室温で一日攪拌した。次いで反応液に水を加えて分液後、中性になるまで洗浄を繰り返した。濃縮後、大量のメタノール中に投入してポリマーを析出させ、濾過、洗浄後、真空乾燥してポリマー(b)を得た。ポリマー(b)をGPC分析したところ、Mn=21000、Mw/Mn=1.10であり、NMRにより測定したアセタール基保護率は42%であった。
比較例1
ポリマー(b)を単独で用いた以外は実施例と同様にして、溶解速度の測定し、露光量と溶解速度の関係をまとめて図1に示す。
Claims (3)
- (A)式(III)
(式中、R 7 は、水素原子、または、フッ素原子で置換されていてもよいC1〜C6アルキル基を表し、R 8 は、酸により分解または脱離する有機基を表し、R 9 は、フッ素原子、またはフッ素原子で置換されていてもよいC1〜C6炭化水素基を表し、rは1〜3のいずれかの整数を表し、sは0または1〜3のいずれかの整数を表し、r+s≦5を表し、rが2以上の場合、R 8 は、同一または相異なっていてもよく、sが2以上の場合、R 9 は同一または相異なっていてもよい。)で表される繰り返し単位を有する重合体である、酸との反応によりアルカリ可溶性となる重合体、
(B)式(I)
(式中、R1、R2はそれぞれ独立に、C1〜C20の炭化水素基を表し、R3は、式(II)
(式中、R 5 は、水素原子または酸で分解または脱離する基を表し、R 6 は、フッ素原子またはフッ素原子で置換されていてもよいC1〜C6の炭化水素基を表し、mは1〜3のいずれかの整数を表し、pは0または1〜3のいずれかの整数を表し、m+p≦5を表し、mが2以上の場合、R 5 は同一または相異なっていてもよく、pが2以上の場合、R 6 は同一または相異なっていてもよい。)で表される基を表す。)で表される繰り返し単位を有する重合体、及び
(C)酸発生剤、
を含有することを特徴とするレジスト組成物。 - 式(I)で表される繰り返し単位を有する重合体の数平均分子量が、2,000〜50,000であることを特徴とする請求項1に記載のレジスト組成物。
- 式(I)で表される繰り返し単位を有する重合体の重量平均分子量(Mw)と数平均分子量(Mn)の比(Mw/Mn)が、1.01〜3.00の範囲であることを特徴とする請求項1または2に記載のレジスト組成物。
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