JP2005091807A - Resist composition - Google Patents
Resist composition Download PDFInfo
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- JP2005091807A JP2005091807A JP2003325607A JP2003325607A JP2005091807A JP 2005091807 A JP2005091807 A JP 2005091807A JP 2003325607 A JP2003325607 A JP 2003325607A JP 2003325607 A JP2003325607 A JP 2003325607A JP 2005091807 A JP2005091807 A JP 2005091807A
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- formula
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- atom
- hydrocarbon
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- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 71
- 229920000642 polymer Polymers 0.000 claims abstract description 53
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 32
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 229910052745 lead Inorganic materials 0.000 claims abstract description 4
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical group [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052718 tin Inorganic materials 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 238000010894 electron beam technology Methods 0.000 abstract description 6
- 125000003277 amino group Chemical group 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 2
- -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
- 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
- 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
- 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
- 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
- 230000000694 effects Effects 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
- 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
- 239000007864 aqueous solution Substances 0.000 description 4
- 229920001577 copolymer Polymers 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
- 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
- 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
- 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
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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
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- 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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Abstract
Description
本発明は、遠紫外線、電子線、X線などの高エネルギー線に対して高い感度を有し、アルカリ水溶液で現像することによりパターン形成できる、微細加工技術に適したレジスト組成物に関する。 The present invention relates to a resist composition suitable for microfabrication technology, which has high sensitivity to high energy rays such as deep ultraviolet rays, electron beams, and X-rays, and can be patterned by developing with an alkaline aqueous solution.
レジストの溶解特性を制御し、パターニング特性を向上させるには、溶解性阻止剤を添加するのが有効であることが知られている。溶解阻止剤には、(1)露光光に対する高透明性(2)エッチング耐性(3)酸の作用によりアルカリ現像液への溶解性が著しく変化する特性が必要とされ、低分子化合物及び高分子化合物が用いられ、高分子化合物とし具体的には、p−ブトキシスチレンとtert−ブチルアクリレートのコポリマーやp−ブトキシスチレンと無水マレイン酸のコポリマー等を例示することができる。(特許文献1を参照)
しかし、従来知られている高分子の溶解阻止剤を用いても、コントラスト性能を向上させるには限界があるという問題があった。 However, there is a problem that there is a limit to improving the contrast performance even when a conventionally known polymer dissolution inhibitor is used.
本発明は、遠紫外線、電子線、X線などの高エネルギー線に対して高い感度を有し、アルカリ水溶液で現像することによりコントラストの優れたパターンを形成できるレジスト組成物を提供することを目的とする。 An object of the present invention is to provide a resist composition that has high sensitivity to high energy rays such as deep ultraviolet rays, electron beams, and X-rays, and can form a pattern with excellent contrast by developing with an alkaline aqueous solution. And
本発明者らは、上記課題を解決すべく鋭意検討した結果、溶解阻止剤として酸により容易に主鎖が開裂する特殊な構造を有するポリマーを用いることにより上記課題を解決することができ、本発明を完成するに到った。 As a result of intensive studies to solve the above problems, the present inventors can solve the above problems by using a polymer having a special structure in which the main chain is easily cleaved by an acid as a dissolution inhibitor. The invention has been completed.
即ち、本発明は、
(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)
That is, the present invention
(1) (A) a polymer that becomes alkali-soluble by reaction with an acid, (B) formula (I)
(式中、R1、R2はそれぞれ独立に、水素原子、ハロゲン原子、C1〜C20の炭化水素基、ヘテロ環基、シアノ基、ニトロ基、C(=O)R4基、S(O)nR4基、P(=O)(R4)2基、M(R4)3基を表し、R3は、C1〜C20の炭化水素基、ヘテロ環基を表し、R4はC1〜C20の炭化水素オキシ基、C1〜C20の炭化水素基、C1〜C20の炭化水素チオ基、モノもしくはジC1〜C20の炭化水素アミノ基を表し、Mは、ケイ素原子、ゲルマニウム原子、スズ原子、鉛原子を表し、nは0、1、または2のいずれかを表す。)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に関し、
(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)
(Wherein R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a C1-C20 hydrocarbon group, a heterocyclic group, a cyano group, a nitro group, a C (═O) R 4 group, S (O ) N R 4 group, P (═O) (R 4 ) 2 group, M (R 4 ) 3 group, R 3 represents a C1-C20 hydrocarbon group or heterocyclic group, and R 4 represents C1 -C20 hydrocarbon oxy group, C1-C20 hydrocarbon group, C1-C20 hydrocarbon thio group, mono- or di-C1-C20 hydrocarbon amino group, M is silicon atom, germanium atom, tin atom A polymer containing a repeating unit represented by the formula: and a lead atom, wherein n represents 0, 1, or 2; and (C) an acid generator. Regarding
(2) In the compound represented by formula (I), R 1 and R 2 each independently represent a C1-C20 hydrocarbon group, and R 3 represents a C1-C20 hydrocarbon group or heterocyclic group. The resist composition as described in (1),
(3) In the compound represented by the formula (I), R 3 represents the formula (II)
(式中、R5は、水素原子、酸で分解または脱離する基を表し、R6は、フッ素原子、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、R5は同一または相異なっていてもよく、pが2以上の場合、R6は同一または相異なっていてもよい。)で表される置換基であることを特徴とする(1)または(2)に記載のレジスト組成物、
(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)
(In the formula, R 5 represents a hydrogen atom or a group that decomposes or leaves with an acid, R 6 represents a fluorine atom or a C1-C6 hydrocarbon group that may be substituted with a fluorine atom, and m represents 1 represents an integer of 1 to 3, p represents an integer of 0 or 1 to 3, represents m + p ≦ 5, and when m is 2 or more, R 5 may be the same or different. , P is 2 or more, R 6 may be the same or different.) The resist composition according to (1) or (2),
(4) The number average molecular weight of the polymer having a repeating unit represented by formula (I) is 2,000 to 50,000, according to any one of (1) to (3) Resist composition,
(5) The ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the polymer having a repeating unit represented by the formula (I) is in the range of 1.01 to 3.00. The resist composition according to any one of (1) to (4),
(6) (A) A polymer that becomes alkali-soluble by reaction with an acid is represented by the formula (III)
(式中、R7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、R8は、酸により分解または脱離する有機基を表し、R9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、R8は、同一または相異なっていてもよく、sが2以上の場合、R9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ことを特徴とする請求項1〜5のいずれかに記載のレジスト組成物に関する。 (Wherein R 7 represents a hydrogen atom or a C1-C6 alkyl group optionally substituted with a fluorine atom, R 8 represents an organic group which is decomposed or eliminated by an acid, and R 9 represents A fluorine atom, or a C1-C6 hydrocarbon group optionally substituted with a fluorine atom, r represents an integer of 1 to 3, s represents an integer of 0 or 1 to 3, r + s ≦ 5, and when r is 2 or more, R 8 may be the same or different, and when s is 2 or more, R 9 may be the same or different. It is a polymer which has a repeating unit, It is related with the resist composition in any one of Claims 1-5 characterized by the above-mentioned.
本発明の組成物を用いることにより、遠紫外線、電子線、X線などの高エネルギー線に対して高い感度を有し、アルカリ水溶液で現像することによりコントラストの優れたパターンを形成でき、産業上の利用価値は高いといえる。 By using the composition of the present invention, it has high sensitivity to high energy rays such as deep ultraviolet rays, electron beams, and X-rays, and it can form a pattern with excellent contrast by developing with an alkaline aqueous solution. Can be said to have high utility value.
本発明の組成物は、(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)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。
(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。
The composition of the present invention contains (A) a polymer that becomes alkali-soluble upon reaction with an acid, (B) a polymer having a repeating unit represented by formula (I), and (C) an acid generator. It is characterized by that.
(I) Polymer that becomes alkali-soluble by reaction with acid As a polymer that has the property of becoming alkali-soluble by reaction with acid, novolac resin, phenol resin, acrylic resin, and copolymers thereof are used. In order to control the solubility, the phenolic hydroxyl group or the carboxylic acid or the like is preferably used by protecting all or a part thereof with an organic group that is decomposed or eliminated by an acid. As a particularly preferred polymer, a polymer having a repeating unit represented by the formula (III) can be exemplified.
式(III)中、R7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、R8は、酸により分解または脱離する有機基を表し、R9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、R8は、同一または相異なっていてもよく、sが2以上の場合、R9は同一または相異なっていてもよい。 In formula (III), R 7 represents a hydrogen atom or a C1-C6 alkyl group optionally substituted with a fluorine atom, R 8 represents an organic group that decomposes or leaves with an acid, and R 9 Represents a fluorine atom or a C1-C6 hydrocarbon group which may be substituted with a fluorine atom, r represents an integer of 1 to 3, and s represents an integer of 0 or 1 to 3. R + s ≦ 5 and when r is 2 or more, R 8 may be the same or different, and when s is 2 or more, R 9 may be the same or different.
R7、及びR9のフッ素原子で置換されていてもよいC1〜C6炭化水素基として具体的には、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、s−ブチル基、イソブチル基、t−ブチル基、n−ペンチル基、トリフルオロメチル基、ジフルオロメチル基、2−フルオロエチル基等を例示することができる。 Specific examples of the C1-C6 hydrocarbon group which may be substituted with a fluorine atom represented by R 7 and R 9 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and an s-butyl group. Group, isobutyl group, t-butyl group, n-pentyl group, trifluoromethyl group, difluoromethyl group, 2-fluoroethyl group and the like can be exemplified.
R8として、具体的には、メトキシメチル基、2−メトキシエトキシメチル基、テトラヒドロピラニル基、4−メトキシテトラヒドロピラニル基、テトラヒドロフラニル基、トリフェニルメチル基、トリメチルシリル基、2−(トリメチルシリル)エトキシメチル基、t−ブチルジメチルシリル基、トリメチルシリルメチル基、又は下式に示すような置換基を例示することができる。 Specific examples of R 8 include methoxymethyl group, 2-methoxyethoxymethyl group, tetrahydropyranyl group, 4-methoxytetrahydropyranyl group, tetrahydrofuranyl group, triphenylmethyl group, trimethylsilyl group, 2- (trimethylsilyl) Examples thereof include an ethoxymethyl group, a t-butyldimethylsilyl group, a trimethylsilylmethyl group, and a substituent as shown in the following formula.
(式中、kは0又は1を表す。)。さらに、下式 (Wherein k represents 0 or 1). Furthermore, the following formula
(式中、R14はC1〜C20の無置換又はアルコキシ置換のアルキル基、C5〜C10のシクロアルキル基、又はC6〜C20の無置換又はアルコキシ置換のアリール基を表し、R15は、水素又はC1〜C3のアルキル基を表し、R16は水素、C1〜C6のアルキル基、又はC1〜C6のアルコキシ基を表す。)で表される基を例示することができ、このような置換基として具体的には、1−メトキシエチル基、1−エトキシエチル基、1−メトキシプロピル基、1−メチル−1−メトキシエチル基、1−(イソプロポキシ)エチル基等を例示することができる。水酸基、またはアルコキシ基(OR8基)の置換位置は特に制限されないが、メタ位又はパラ位が好ましい。 Wherein R 14 represents a C1-C20 unsubstituted or alkoxy-substituted alkyl group, a C5-C10 cycloalkyl group, or a C6-C20 unsubstituted or alkoxy-substituted aryl group, and R 15 represents hydrogen or A C1-C3 alkyl group, and R 16 represents a hydrogen, a C1-C6 alkyl group, or a C1-C6 alkoxy group). Specific examples include 1-methoxyethyl group, 1-ethoxyethyl group, 1-methoxypropyl group, 1-methyl-1-methoxyethyl group, 1- (isopropoxy) ethyl group and the like. The substitution position of the hydroxyl group or alkoxy group (OR 8 group) is not particularly limited, but the meta position or para position is preferred.
酸によりアルカリ可溶性となる重合体として、具体的には、下記単量体を用いた単独重合体及び共重合体を例示することができる。 Specific examples of the polymer that becomes alkali-soluble by an acid include homopolymers and copolymers using the following monomers.
4−ヒドロキシスチレン、3−ヒドロキシスチレン、4−ヒドロキシ−α−メチルスチレン、4−t−ブトキシスチレン、3−t−ブトキシスチレン、4−t−ブトキシ−α−メチルスチレン、4−(1’−エトキシ−エトキシ)スチレン、3−(1’−エトキシ−エトキシ)スチレン、4−(1’−エトキシ−エトキシ)−α−メチルスチレン、4−(1’−エトキシ−プロポキシ)スチレン、3−(1’−エトキシ−プロポキシ)スチレン、4−(1’−エトキシ−プロポキシ)−α−メチルスチレン、4−(1’−シクロヘキシル−エトキシ)スチレン、3−(1’−シクロヘキシル−エトキシ)スチレン、4−(1’−シクロヘキシル−エトキシ)−α−メチルスチレン、4−(1’−ブトキシ−エトキシ)スチレン、3−(1’−ブトキシ−エトキシ)スチレン、4−(1’−ブトキシ−エトキシ)−α−メチルスチレン、4−t−ブトキシカルボニルオキシスチレン、3−t−ブトキシカルボニルオキシスチレン、4−t−ブトキシカルボニルオキシ−α−メチルスチレン、4−テトラヒドロピラニルスチレン、3−テトラヒドロピラニルスチレン、4−テトラヒドロピラニル−α−メチルスチレン、4−テトラヒドロフラニルスチレン、3−テトラヒドロフラニルスチレン、4−テトラヒドロフラニル−α−メチルスチレン、アクリル酸、メタクリル酸、イタコン酸、アクリル酸−t−ブチル、メタクリル酸−t−ブチル、イタコン酸ジ−t−ブチル、アクリル酸−t−アミル、メタクリル酸−t−アミル、イタコン酸ジ−t−アミル、アクリル酸−1−アルキルシクロペンチル、メタクリル酸−1−アルキルシクロペンチル、イタコン酸ジ−1−アルキルシクロペンチル、アクリル酸−1−アルキルシクロヘキシル、メタクリル酸−1−アルキルシクロヘキシル、イタコン酸ジ−1−アルキルシクロヘキシル、アクリル酸−1−アルキルシクロペンテニル、メタクリル酸−1−アルキルシクロペンテニル、イタコン酸ジ−1−アルキルシクロペンテニル、アクリル酸−1−アルキルシクロヘキセニル、メタクリル酸−1−アルキルシクロヘキセニル、イタコン酸ジ−1−アルキルシクロヘキセニル、アクリル酸アルキルアダマンチル、メタクリル酸アルキルアダマンチル、ノルボルネンカルボン酸−t−ブチル、ノルボルネンカルボン酸−t−アミル、ノルボルネンカルボン酸−1−アルキルシクロペンチル、ノルボルネンカルボン酸−1−アルキルシクロヘキシル、ノルボルネンカルボン酸−t−アミル、ノルボルネンカルボン酸−1−アルキルシクロペンチル、ノルボルネンカルボン酸−1−アルキルシクロヘキシル、ノルボルネンカルボン酸−1−アルキルシクロペンテニル、ノルボルネンカルボン酸−1−アルキルシクロヘキセニル等。 4-hydroxystyrene, 3-hydroxystyrene, 4-hydroxy-α-methylstyrene, 4-t-butoxystyrene, 3-t-butoxystyrene, 4-t-butoxy-α-methylstyrene, 4- (1′- Ethoxy-ethoxy) styrene, 3- (1′-ethoxy-ethoxy) styrene, 4- (1′-ethoxy-ethoxy) -α-methylstyrene, 4- (1′-ethoxy-propoxy) styrene, 3- (1 '-Ethoxy-propoxy) styrene, 4- (1'-ethoxy-propoxy) -α-methylstyrene, 4- (1'-cyclohexyl-ethoxy) styrene, 3- (1'-cyclohexyl-ethoxy) styrene, 4- (1′-cyclohexyl-ethoxy) -α-methylstyrene, 4- (1′-butoxy-ethoxy) styrene, 3- (1′-buto X-ethoxy) styrene, 4- (1′-butoxy-ethoxy) -α-methylstyrene, 4-t-butoxycarbonyloxystyrene, 3-t-butoxycarbonyloxystyrene, 4-t-butoxycarbonyloxy-α- Methyl styrene, 4-tetrahydropyranyl styrene, 3-tetrahydropyranyl styrene, 4-tetrahydropyranyl-α-methyl styrene, 4-tetrahydrofuranyl styrene, 3-tetrahydrofuranyl styrene, 4-tetrahydrofuranyl-α-methyl styrene, Acrylic acid, methacrylic acid, itaconic acid, acrylic acid-t-butyl, methacrylic acid-t-butyl, itaconic acid di-t-butyl, acrylic acid-t-amyl, methacrylic acid-t-amyl, itaconic acid di-t -Amyl, acrylic acid-1-alkylcyclope Til, methacrylic acid-1-alkylcyclopentyl, di-1-alkylcyclopentyl itaconate, acrylic acid-1-alkylcyclohexyl, methacrylic acid-1-alkylcyclohexyl, itaconic acid di-1-alkylcyclohexyl, acrylic acid-1-alkyl Cyclopentenyl, methacrylate-1-alkylcyclopentenyl, di-1-alkylcyclopentenyl itaconate, -1-alkylcyclohexenyl acrylate, -1-alkylcyclohexenyl methacrylate, di-1-alkylcyclohexenyl itaconate, Alkyl adamantyl acrylate, alkyl adamantyl methacrylate, norbornenecarboxylic acid-t-butyl, norbornenecarboxylic acid-t-amyl, norbornenecarboxylic acid-1-alkylcyclopentyl, Rubornenecarboxylic acid-1-alkylcyclohexyl, norbornenecarboxylic acid-t-amyl, norbornenecarboxylic acid-1-alkylcyclopentyl, norbornenecarboxylic acid-1-alkylcyclohexyl, norbornenecarboxylic acid-1-alkylcyclopentenyl, norbornenecarboxylic acid -1-alkylcyclohexenyl and the like.
上記単量体から製造される重合体中、酸分解性または脱離性保護基により保護されたフェノール類又は酸分解性または脱離性保護基により保護されたカルボン酸類と保護されていないフェノール類又はカルボン酸類を含むのが好ましい。酸分解性または脱離性保護基により保護された単量体と、保護されていない単量体から製造される共重合体において、保護基の置換度はOH基の5〜50モル%、好ましくは10〜30モル%が好ましい。5モル%以上では、レジスト膜の膜べりが小さくなり、50モル%以下の場合、解像力が低下することが少ない。また、その重量平均分子量は5,000〜100,000とすることが好ましい。 In polymers produced from the above monomers, phenols protected by acid-decomposable or detachable protecting groups or carboxylic acids protected by acid-decomposable or detachable protecting groups and unprotected phenols Or it is preferable that carboxylic acids are included. In a copolymer produced from a monomer protected with an acid-decomposable or detachable protecting group and an unprotected monomer, the degree of substitution of the protecting group is preferably 5 to 50 mol% of the OH group, preferably Is preferably 10 to 30 mol%. When the amount is 5 mol% or more, the resist film is less rubbed, and when the amount is 50 mol% or less, the resolving power hardly decreases. Moreover, it is preferable that the weight average molecular weight shall be 5,000-100,000.
また、必要に応じてその他の性質、即ち基盤密着性や耐エッチング性等を持たせるための、酸による溶解速度変化には関与しない単量体、又は酸との反応に関与しない単量体を一緒に用いることができる。そのような単量体として、具体的には、スチレン、メトキシスチレン、エトキシスチレン、プロポキシスチレン、イソプロポキシスチレン等のアルコキシスチレン類、メチルカルボキシスチレン、エチルカルボキシスチレン、プロポキシカルボキシスチレン、イソプロポキシカルボキシスチレン等のアルコキシカルボキシスチレン類、2−ヒドロキシエトキシスチレン、2−ヒドロキシプロポキシスチレン等のヒドロキシアルコキシスチレン類、無水マレイン酸、ノルボルネン、ヒドロキシノルボルネン、ジヒドロキシノルボルネン等のノルボルネン誘導体等が例示することができ、これらの単量体は単独でも2種以上を混合して用いることもできる。
(II)式(I)で表される繰り返し単位を有する重合体。
Further, if necessary, a monomer that does not participate in a change in dissolution rate due to an acid or a monomer that does not participate in a reaction with an acid in order to provide other properties, that is, adhesion to the substrate, etching resistance, etc. Can be used together. Specific examples of such monomers include alkoxystyrenes such as styrene, methoxystyrene, ethoxystyrene, propoxystyrene, and isopropoxystyrene, methylcarboxystyrene, ethylcarboxystyrene, propoxycarboxystyrene, and isopropoxycarboxystyrene. Examples thereof include hydroxycarboxystyrenes such as 2-hydroxyethoxystyrene and 2-hydroxypropoxystyrene, and norbornene derivatives such as maleic anhydride, norbornene, hydroxynorbornene and dihydroxynorbornene. The monomers can be used alone or in admixture of two or more.
(II) A polymer having a repeating unit represented by the formula (I).
本発明に用いられる式(I)で表される繰り返し単位中、R1、R2はそれぞれ独立に、水素原子、フッ素原子、C1〜C20の炭化水素基、ヘテロ環基、シアノ基、ニトロ基、C(=O)R4基、S(O)nR4基、P(=O)(R4)2基、M(R4)3基を表し、R4はC1〜C20の炭化水素オキシ基、C1〜C20の炭化水素基、C1〜C20の炭化水素チオ基、モノもしくはジC1〜C20の炭化水素置換アミノ基を表し、Mは、ケイ素原子、ゲルマニウム原子、スズ原子、鉛原子を表し、nは0、1、または2を表す。R1、R2として具体的には、水素原子、フッ素原子、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、t−ブチル基、s−ブチル基、イソブチル基、n−ペンチル基、s−ペンチル基、イソペンチル基、ネオペンチル基、n−ヘキシル基、s−ヘキシル基、1,1−ジメチル−n−ヘキシル基、n−ヘプチル基、n−デシル基、n−ドデシル基等C1〜C20のアルキル基、ビニル基、アリル基、2−ブテニル基、1−メチル−2−プロペニル基、4−オクテニル基等のC2〜C20のアルキニル基、エチニル基、プロパルギル基、1−メチル−プロピニル基等のC2〜C20のアルキニル基、シクロプロピル基、シクロブチル基、シクロペンチル基、1−メチルシクロペンチル基、1−メチルシクロヘキシル基、1−アダマンチル基、1−メチルアダマンチル基、2−アダマンチル基、2−メチル−2−アダマンチル基、ノルボルニル基等のC3〜C20の脂環式炭化水素基、フェニル基、1−ナフチル基、9−アントラセニル基等のC6〜C20の芳香族炭化水素基、2−ピリジル基、3―ピリジル基、4−ピリジル基、2−フラニル基、2−チエニル基、3−チエニル基、1−ピロロ基、2−オキサゾリル基、3−イソオキサゾリル基、2−チアゾリル基、3−イソチアゾリル基、1−ピラゾリル基、4−ピラゾリル基、2−イミダゾリル基、1,3,4−オキサジアゾール−2−イル、1,2,4−オキサジアゾール−5−イル、1,3,4−チアジアゾール−2−イル、1,2,4−チアジアゾール−5−イル、1,3,4−トリアゾール−2−イル、1,2,3−チアジアゾール−5−イル、1,2,3−トリアゾール−4−イル、1,2,3,4−テトラゾール−5−イル、ピリミジン−2−イル、ピリミジン−4−イル、ピラジン−2−イル、ピリダジン−3−イル、1,2,4−トリアジン−6−イル、1,3,5−トリアジン−2−イル、1−ピロリジニル基、1−ピペリジル基、4−モルホリニル基、2−テトラヒドロフラニル基、4−テトラヒドロピラニル基等のヘテロ環基、メトキシカルボニル基、エトキシカルボニル基、n−プロポキシカルボニル基、イソプロポキシカルボニル基、n−ブトキシカルボニル基、t−ブトキシカルボニル基等のC1〜C20のアルコキシカルボニル基、メチルチオカルボニル基等のC1〜C20アルキルチオカルボニル基、N,N−ジメチルカルバモイル基等の置換または無置換カルバモイル基、メチルスルフェニル基、フェニルスルフェニル基、メチルスルフィニル基、フェニルスルフェニル基、メチルスルホニル基、フェニルスルホニル基、メチルスルフリル基、N、N−ジメチルスルファモイル基等の置換または無置換スルファモイル基、ジメチルホスホニル基、ビスメチルチオホスホニル基、テトラメチルアミノホスホニル基等のホスホニル基、トリメチルシリル基、t−ブチルジメチルシリル基、フェニルジメチルシリル基、トリメチルスタンニル基、トリフェニルプランバンニル基等を例示することができる。 In the repeating unit represented by the formula (I) used in the present invention, R 1 and R 2 are each independently a hydrogen atom, a fluorine atom, a C1-C20 hydrocarbon group, a heterocyclic group, a cyano group, or a nitro group. , C (═O) R 4 group, S (O) n R 4 group, P (═O) (R 4 ) 2 group, M (R 4 ) 3 group, and R 4 is a C1-C20 hydrocarbon. Represents an oxy group, a C1-C20 hydrocarbon group, a C1-C20 hydrocarbon thio group, a mono- or di-C1-C20 hydrocarbon-substituted amino group, and M represents a silicon atom, a germanium atom, a tin atom, or a lead atom. N represents 0, 1, or 2. Specific examples of R 1 and R 2 include hydrogen atom, fluorine atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, s-butyl group, isobutyl group, n -Pentyl group, s-pentyl group, isopentyl group, neopentyl group, n-hexyl group, s-hexyl group, 1,1-dimethyl-n-hexyl group, n-heptyl group, n-decyl group, n-dodecyl group C1-C20 alkyl group, vinyl group, allyl group, 2-butenyl group, 1-methyl-2-propenyl group, 4-octenyl group, etc. C2-C20 alkynyl group, ethynyl group, propargyl group, 1-methyl -C2-C20 alkynyl group such as propynyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, 1-methylcyclopentyl group, 1-methylcyclohexyl group, -C3-C20 alicyclic hydrocarbon group such as adamantyl group, 1-methyladamantyl group, 2-adamantyl group, 2-methyl-2-adamantyl group, norbornyl group, phenyl group, 1-naphthyl group, 9-anthracenyl C6-C20 aromatic hydrocarbon group such as a group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-furanyl group, 2-thienyl group, 3-thienyl group, 1-pyrrolo group, 2- Oxazolyl group, 3-isoxazolyl group, 2-thiazolyl group, 3-isothiazolyl group, 1-pyrazolyl group, 4-pyrazolyl group, 2-imidazolyl group, 1,3,4-oxadiazol-2-yl, 1,2 , 4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-triazol-2-yl Yl, 1,2,3-thiadiazol-5-yl, 1,2,3-triazol-4-yl, 1,2,3,4-tetrazol-5-yl, pyrimidin-2-yl, pyrimidine-4- Yl, pyrazin-2-yl, pyridazin-3-yl, 1,2,4-triazin-6-yl, 1,3,5-triazin-2-yl, 1-pyrrolidinyl group, 1-piperidyl group, 4- Heterocyclic groups such as morpholinyl group, 2-tetrahydrofuranyl group, 4-tetrahydropyranyl group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl C1-C20 alkoxycarbonyl group such as a group, C1-C20 alkylthiocarbonyl group such as methylthiocarbonyl group, N, N- Substituted or unsubstituted carbamoyl groups such as methylcarbamoyl group, methylsulfenyl group, phenylsulfenyl group, methylsulfinyl group, phenylsulfenyl group, methylsulfonyl group, phenylsulfonyl group, methylsulfuryl group, N, N-dimethylsulfa Substituted or unsubstituted sulfamoyl group such as moyl group, phosphonyl group such as dimethylphosphonyl group, bismethylthiophosphonyl group, tetramethylaminophosphonyl group, trimethylsilyl group, t-butyldimethylsilyl group, phenyldimethylsilyl group, trimethylstane Examples thereof include a nyl group and a triphenylplanvanyl group.
また、R3は、C1〜C20の炭化水素基、ヘテロ環基を表し、具体的には、R1、R2で例示したのと同様の置換基を例示することができる。 R 3 represents a C1 to C20 hydrocarbon group or heterocyclic group, and specific examples thereof include the same substituents as exemplified for R 1 and R 2 .
以上のように示したR1〜R3の置換基各々は、適当な炭素上の位置にさらに置換基を有することができる。その置換基としては、フッ素原子、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、t−ブチル基、n−ヘキシル基、フルオロメチル基、ジフロロメチル基、トリフルオロメチル基、パーフルオロエチル基、シクロプロプル基、シクロヘキシル基、ビニル基、アリル基、フェニル基、4−クロロフェニル基、4−メトキシフェニル基、3,4−ジメチルフェニル基等の置換フェニル基、プロパルギル基、2−ヒドロキシ−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル基、2−(エトキシメトキシ)−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル基等の炭化水素基、メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、s−ブトキシ基、イソブトキシ基、t−ブトキシ基、フルオロメトキシ基、ジフオロメトキシ基、トリフルオロメトキシ基、フェノキシ基、4−クロロフェノキシ基、ベンジルオキシ基、フェネチルオキシ基、t−ブトキシカルボニルオキシ基、テトラヒドロピラニルオキシ基、フェノキシエトキシ基、エトキシエトキシ基、トリメチルシリルオキシ基、t−ブトキシカルボニルメトキシ基等のアルコキシ基、アミノ基、メチルアミノ基、ジメチルアミノ基、t−ブトキシカルボニルアミノ基等のアミノ基、メチルチオ基、フェニルチオ基、2−ピリジルチオ基、メチルスルフィニル基、メチルスルホニル基等のアルキル、アリール、もしくはヘテロ環チオ基またはその酸化体、メトキシカルボニル基、エトキシカルボニル基、n−プロポキシカルボニル基、イソプロポキシカルボニル基、n−ブトキシカルボニル基、t−ブトキシカルボニル基等のC1〜C20のアルコキシカルボニル基、アセチル基、プロパノイル基、ベンゾイル基、2−ピリジルカルボニル基等のC2〜C20のアシル基、シアノ基、ニトロ基等を例示することができる。 Each of the substituents R 1 to R 3 shown above can further have a substituent at an appropriate carbon position. As the substituent, fluorine atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, n-hexyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, Perfluoroethyl group, cyclopropyl group, cyclohexyl group, vinyl group, allyl group, phenyl group, 4-chlorophenyl group, 4-methoxyphenyl group, substituted phenyl group such as 3,4-dimethylphenyl group, propargyl group, 2-hydroxy Carbonization of -1,1,1,3,3,3-hexafluoro-2-propyl group, 2- (ethoxymethoxy) -1,1,1,3,3,3-hexafluoro-2-propyl group, etc. Hydrogen group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, s-butoxy group, isobutoxy group, t-butyl group Xyl group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, phenoxy group, 4-chlorophenoxy group, benzyloxy group, phenethyloxy group, t-butoxycarbonyloxy group, tetrahydropyranyloxy group, phenoxyethoxy group, ethoxy Alkoxy groups such as ethoxy group, trimethylsilyloxy group, t-butoxycarbonylmethoxy group, amino group, methylamino group, dimethylamino group, amino group such as t-butoxycarbonylamino group, methylthio group, phenylthio group, 2-pyridylthio group Alkyl, aryl, or heterocyclic thio group such as methylsulfinyl group and methylsulfonyl group or its oxidant, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group Group, C1-C20 alkoxycarbonyl group such as n-butoxycarbonyl group, t-butoxycarbonyl group, C2-C20 acyl group such as acetyl group, propanoyl group, benzoyl group, 2-pyridylcarbonyl group, cyano group, nitro group Examples include groups.
これら置換基を有するR1〜R3の具体例としては、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、2,2,2−トリフルオロエチル基、ペンタフルオロエチル基、3,3,3−トリフルオロプロピル基、1,1,2,3,3,3−ヘキサフルオロプロピル基等のハロアルキル基、テトラフルオロエテニル基、2,2−ジフロロエテニル基等のハロアルケニル基、メトキシメチル基、メトキシエチル基、フェノキシメチル等のアルコキシアルキル基、メチルチオメチル基、フェニルチオメチル基等のアルキルチオアルキル基またはアリールチオアルキル基、ベンジル基、ジフェニルメチル基、トリチル基、フェネチル基等のアラルキル基、ベンゾイルメチル基、アセチルメチル基等のアシルアルキル基、シアノメチル基等を例示することができる。 Specific examples of R 1 to R 3 having these substituents include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, 3, 3, 3 -Haloalkyl groups such as trifluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, haloalkenyl groups such as tetrafluoroethenyl group, 2,2-difluoroethenyl group, methoxymethyl group, methoxy Alkylalkyl group such as ethyl group, phenoxymethyl, alkylthioalkyl group such as methylthiomethyl group, phenylthiomethyl group or arylthioalkyl group, benzyl group, diphenylmethyl group, trityl group, phenethyl group, aralkyl group, benzoylmethyl group , Acylalkyl groups such as acetylmethyl group, cyanomethyl groups, etc. It can be exemplified.
また、R3として特に、式(II)で表される置換基を好ましく例示することができる。式(II)で表される置換基中、R5は、水素原子、酸により分解または脱離する基を表し、mは1〜3のいずれかの整数を表し、mが2以上の場合、R5は、同一または相異なっていてもよい。ここで、酸により分解または脱離する基として、具体的には、R8で例示したものと同様の置換基を例示することができる。 Further, as R 3 , a substituent represented by the formula (II) can be preferably exemplified. In the substituent represented by the formula (II), R 5 represents a hydrogen atom, a group that decomposes or leaves with an acid, m represents an integer of 1 to 3, and when m is 2 or more, R 5 may be the same or different. Here, specific examples of the group that can be decomposed or eliminated by an acid include the same substituents as those exemplified for R 8 .
また、R6は、フッ素原子、またはC1〜C20の炭化水素基を表し、具体的には、R1、R2で例示した置換基のうち該当する例示と同様の置換基を例示することができ、その置換位置は特に制限されない。pは、0または1〜3のいずれかの整数を表し、m+p≦5の関係を有し、pが2以上の場合、R6は、同一または相異なっていてもよい。 R 6 represents a fluorine atom or a C1-C20 hydrocarbon group. Specifically, among the substituents exemplified for R 1 and R 2 , the same substituents as the corresponding examples may be exemplified. The substitution position is not particularly limited. p represents an integer of 0 or 1 to 3, and has a relationship of m + p ≦ 5. When p is 2 or more, R 6 may be the same or different.
式(II)で表される置換基として具体的には、4−ヒドロキシフェニル基、4−ヒドロキシ−3−メチルフェニル基、4−t−ブトキシフェニル基、4−テトラヒドロピラニルオキシフェニル基、4−フェノキシエトキシフェニル基、4−トリメチルシリルオキシフェニル基、4−t−ブトキシカルボニルオキシフェニル基、4−t−ブトキシカルボニルメトキシフェニル基、2,3−ジフルオロ−4−ヒドロキシフェニル基、2,3−ジフルオロ−4−t−ブトキシフェニル基、2,6−ジフルオロ−4−ヒドロキシフェニル基、2,6−ジフルオロ−4−t−ブトキシフェニル基、3,5−ジフルオロ−4−ヒドロキシフェニル基、3,5−ジフルオロ−4−t−ブトキシフェニル基、2,3,5,6−テトラフルオロ−4−ヒドロキシフェニル基、2,3,5,6−テトラフルオロ−4−t−ブトキシフェニル基、2−トリフルオロメチル−4−ヒドロキシフェニル基、2−トリフルオロメチル−4−t−ブトキシフェニル基、2−トリフルオロメチル−6−フルオロ−4−ヒドロキシフェニル基、2−トリフルオロメチル−6−フルオロ−4−t−ブトキシフェニル基、3−トリフルオロメチル−5−フロロ−4−ヒドロキシフェニル基、3−トリフルオロメチル−5−フロロ−4−t−ブトキシフェニル基、4−(1−エトキシエトキシ)フェニル基、4−(2−ヒドロキシ−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル)フェニル基、4−(2−エトキシメトキシ−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル)フェニル基等を例示することができる。 Specific examples of the substituent represented by the formula (II) include 4-hydroxyphenyl group, 4-hydroxy-3-methylphenyl group, 4-t-butoxyphenyl group, 4-tetrahydropyranyloxyphenyl group, 4 -Phenoxyethoxyphenyl group, 4-trimethylsilyloxyphenyl group, 4-t-butoxycarbonyloxyphenyl group, 4-t-butoxycarbonylmethoxyphenyl group, 2,3-difluoro-4-hydroxyphenyl group, 2,3-difluoro -4-t-butoxyphenyl group, 2,6-difluoro-4-hydroxyphenyl group, 2,6-difluoro-4-t-butoxyphenyl group, 3,5-difluoro-4-hydroxyphenyl group, 3,5 -Difluoro-4-t-butoxyphenyl group, 2,3,5,6-tetrafluoro-4-hydroxy Phenyl group, 2,3,5,6-tetrafluoro-4-t-butoxyphenyl group, 2-trifluoromethyl-4-hydroxyphenyl group, 2-trifluoromethyl-4-t-butoxyphenyl group, 2- Trifluoromethyl-6-fluoro-4-hydroxyphenyl group, 2-trifluoromethyl-6-fluoro-4-t-butoxyphenyl group, 3-trifluoromethyl-5-fluoro-4-hydroxyphenyl group, 3- Trifluoromethyl-5-fluoro-4-t-butoxyphenyl group, 4- (1-ethoxyethoxy) phenyl group, 4- (2-hydroxy-1,1,1,3,3,3-hexafluoro-2 -Propyl) phenyl group, 4- (2-ethoxymethoxy-1,1,1,3,3,3-hexafluoro-2-propyl) phenyl group and the like. Can.
また、R3の好ましい態様として例示した式(II)で表される置換基は、さらにR1、R2の置換基としても好ましく例示することができる。 Further, the substituent represented by the formula (II) exemplified as a preferred embodiment of R 3 can be preferably exemplified as the substituent of R 1 and R 2 .
また、R1〜R3で表される各置換基は、式(I)で表される各繰り返し単位全てにおいて同一である必要はなく、適宜2種以上を混合して用いることができる。例えば、R3の置換基として、p−メトキシフェニル基とp−(1−エトキシエトキシ)フェニル基をモル比で1/99〜99/1の比率で混合して用いることができる。 In addition, the substituents represented by R 1 to R 3 do not have to be the same in all the repeating units represented by the formula (I), and two or more kinds can be appropriately mixed and used. For example, as a substituent for R 3 , a p-methoxyphenyl group and a p- (1-ethoxyethoxy) phenyl group can be mixed at a molar ratio of 1/99 to 99/1.
本発明における式(I)で表される繰り返し単位を有する重合体とは、式(I)で表される繰り返し単位のみからなる重合体、並びに式(I)で表される繰り返し単位及び式(I)で表される繰り返し単位以外の繰り返し単位からなる重合体を意味する。 The polymer having a repeating unit represented by the formula (I) in the present invention includes a polymer consisting only of the repeating unit represented by the formula (I), and the repeating unit represented by the formula (I) and the formula (I The polymer which consists of repeating units other than the repeating unit represented by I) is meant.
式(I)で表される繰り返し単位以外の繰り返し単位として、具体的には、式(IV)で表される繰り返し単位等を例示することができる。 Specific examples of the repeating unit other than the repeating unit represented by the formula (I) include a repeating unit represented by the formula (IV).
式(IV)中、R31、R32、R33は、それぞれ独立に、水素原子、フッ素原子、C1〜20直線状、分岐状、もしくは環状のアルキル基または、フッ素化されたアルキル基を表し、R34は、水酸基、またはアルコキシ基で置換されていてもよいC6〜20の芳香族炭化水素基、またはCO2R35基を表し、R35は、C1〜C20炭化水素基を表し、好ましくは酸不安定基を表す。 In the formula (IV), R 31 , R 32 and R 33 each independently represents a hydrogen atom, a fluorine atom, a C1-20 linear, branched or cyclic alkyl group or a fluorinated alkyl group. , R 34 represents a hydroxyl group or a C 6-20 aromatic hydrocarbon group which may be substituted with an alkoxy group, or a CO 2 R 35 group, and R 35 represents a C 1 to C 20 hydrocarbon group, preferably Represents an acid labile group.
この場合、炭素数1〜20の直鎖状、分岐状もしくは環状のアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基、シクロペンチル基、シクロヘキシル基、2−エチルヘキシル基、n−オクチル基等を例示でき、特に炭素数1〜12、とりわけ炭素数1〜10のものが好ましい。なお、フッ素化されたアルキル基は、上記アルキル基の水素原子の一部又は全部がフッ素原子で置換されたものであり、トリフルオロメチル基、2,2,2−トリフルオロエチル基、3,3,3−トリフルオロプロピル基、1,1,2,3,3,3−ヘキサフルオロプロピル基などが挙げられる。 In this case, as the linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, A cyclopentyl group, a cyclohexyl group, a 2-ethylhexyl group, an n-octyl group and the like can be exemplified, and those having 1 to 12 carbon atoms, particularly 1 to 10 carbon atoms are preferable. The fluorinated alkyl group is one in which part or all of the hydrogen atoms of the alkyl group are substituted with fluorine atoms, and includes a trifluoromethyl group, a 2,2,2-trifluoroethyl group, 3, Examples include 3,3-trifluoropropyl group and 1,1,2,3,3,3-hexafluoropropyl group.
R34における水酸基または水素原子が置換された水酸基で置換されていてもよいC6〜20の芳香族炭化水素基として、具体的には、下記式(V)で表される置換基を例示することができる。 As the aromatic hydrocarbon group C6~20 hydroxyl group or a hydrogen atom may be substituted with a hydroxyl group which is substituted in R 34, specifically, to illustrate the substituent represented by the following formula (V) Can do.
式中、R40は炭素数1〜14の直鎖状、分岐状もしくは環状のアルキル基又はフッ素化されたアルキル基を示し、その具体例は、上記R31で例示した具体例と同様の置換基を例示することができ、Xはフッ素原子、R41は、C1〜C20炭化水素基を表し、好ましくは酸不安定基を表す。a、b、c、dはそれぞれ0または1〜5のいずれかの整数を表し、a+b+c+dは0〜5のいずれかである。 In the formula, R 40 represents a linear, branched or cyclic alkyl group having 1 to 14 carbon atoms or a fluorinated alkyl group, and specific examples thereof are the same substitutions as the specific examples illustrated for R 31 above. Examples of the group include X, a fluorine atom, and R 41 a C1-C20 hydrocarbon group, preferably an acid labile group. a, b, c, and d each represent an integer of 0 or 1 to 5, and a + b + c + d is any of 0 to 5.
R41中、C1〜C20の炭化水素基としては、R1で例示した置換基と同様の置換基を例示することができる、また、酸不安定基としては、種々選定されるが、具体的には下記式(VI)、(VII)、もしくは(VIII)で表される基、各アルキル基の炭素数1〜6のトリアルキルシリル基、炭素数4〜20のオキソアルキル基等を例示することができる。 In R 41 , the C1-C20 hydrocarbon group can be exemplified by the same substituents as those exemplified for R 1 , and various acid labile groups can be selected. Examples include groups represented by the following formula (VI), (VII), or (VIII), trialkylsilyl groups having 1 to 6 carbon atoms, oxoalkyl groups having 4 to 20 carbon atoms, and the like of each alkyl group. be able to.
式(VI)、(VII)においてR51、R54は炭素数1〜20の直鎖状、分岐状もしくは環状のアルキル基等の1価炭化水素基であり、酸素原子、硫黄原子、窒素原子、フッ素原子等のヘテロ原子を含んでもよい。 In the formulas (VI) and (VII), R 51 and R 54 are monovalent hydrocarbon groups such as linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, oxygen atoms, sulfur atoms, nitrogen atoms And may contain a hetero atom such as a fluorine atom.
R52、R53は水素原子又は炭素数1〜20の直鎖状、分岐状もしくは環状のアルキル基であり、酸素原子、硫黄原子、窒素原子、フッ素原子などのヘテロ原子を含んでもよい。また、R52とR53、R52とR54、R53とR54はそれぞれ結合して環を形成してもよい。hは0または1〜10のいずれかの整数を表す。 R 52 and R 53 are a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, and may contain a hetero atom such as an oxygen atom, a sulfur atom, a nitrogen atom or a fluorine atom. R 52 and R 53 , R 52 and R 54 , and R 53 and R 54 may be bonded to each other to form a ring. h represents 0 or an integer of 1 to 10.
より好ましくは、R51〜R54は下記の基であることがよい。R51は炭素数4〜20、好ましくは4〜15の三級アルキル基、各アルキル基がそれぞれ炭素数1〜6のトリアルキルシリル基、炭素数4〜20のオキソアルキル基又は上記式(VIII)で示される基を示し、三級アルキル基として具体的には、tert−ブチル基、tert−アミル基、1,1−ジエチルプロピル基、1−エチルシクロペンチル基、1−ブチルシクロペンチル基、1−エチルシクロヘキシル基、1−ブチルシクロヘキシル基、1−エチル−2−シクロペンテニル基、1−エチル−2−シクロヘキセニル基、2−メチル−2−アダマンチル基等が挙げられ、トリアルキルシリル基として具体的には、トリメチルシリル基、トリエチルシリル基、ジメチル−tert−ブチルシリル基等が挙げられ、オキソアルキル基として具体的には、3−オキソシクロヘキシル基、4−メチル−2−オキソオキサン−4−イル基、5−メチル−5−オキソオキソラン−4−イル基等が挙げられる。 More preferably, R 51 to R 54 are the following groups. R 51 is a tertiary alkyl group having 4 to 20 carbon atoms, preferably 4 to 15 carbon atoms, each alkyl group is a trialkylsilyl group having 1 to 6 carbon atoms, an oxoalkyl group having 4 to 20 carbon atoms, or the above formula (VIII And a tertiary alkyl group specifically includes a tert-butyl group, a tert-amyl group, a 1,1-diethylpropyl group, a 1-ethylcyclopentyl group, a 1-butylcyclopentyl group, 1- Specific examples of the trialkylsilyl group include an ethylcyclohexyl group, 1-butylcyclohexyl group, 1-ethyl-2-cyclopentenyl group, 1-ethyl-2-cyclohexenyl group, and 2-methyl-2-adamantyl group. Include trimethylsilyl group, triethylsilyl group, dimethyl-tert-butylsilyl group, etc. The body, the 3-oxo-cyclohexyl group, 4-methyl-2-oxooxan-4-yl group, and 5-methyl-5-oxo-dioxolane-4-yl group.
R52、R53は水素原子又は炭素数1〜18、好ましくは1〜10の直鎖状、分岐状又は環状のアルキル基を示し、具体的にはメチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基、シクロペンチル基、シクロヘキシル基、2−エチルヘキシル基、n−オクチル基等を例示できる。R54は炭素数1〜18、好ましくは1〜10の酸素原子等のヘテロ原子を有してもよい1価の炭化水素基を示し、直鎖状、分岐状、環状のアルキル基、これらの水素原子の一部が水酸基、アルコキシ基、オキソ基、アミノ基、アルキルアミノ基等に置換されたものを挙げることができ、具体的には、4−ヒドロキシブチル基、2−ブトキシエチル基、4−ヒドロキシメチル−1−シクロヘキシルメチル基、2−ヒドロキシエトキシ−2−エチル基、6−ヒドロキシヘキシル基、1,3−ジオキソラン−2−オン−4−メチル基等の置換アルキル基等が例示できる。 R 52 and R 53 each represent a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, specifically a methyl group, an ethyl group, a propyl group or an isopropyl group. N-butyl group, sec-butyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, 2-ethylhexyl group, n-octyl group and the like. R 54 represents a monovalent hydrocarbon group which may have a hetero atom such as an oxygen atom having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, a linear, branched, or cyclic alkyl group, Examples include those in which a part of hydrogen atoms are substituted with a hydroxyl group, an alkoxy group, an oxo group, an amino group, an alkylamino group, and the like. Specifically, a 4-hydroxybutyl group, a 2-butoxyethyl group, 4 Examples thereof include substituted alkyl groups such as -hydroxymethyl-1-cyclohexylmethyl group, 2-hydroxyethoxy-2-ethyl group, 6-hydroxyhexyl group and 1,3-dioxolan-2-one-4-methyl group.
R52とR53、R52とR54、R53とR54とは環を形成してもよく、環を形成する場合にはR52、R53、R54はそれぞれ炭素数1〜18、好ましくは1〜10の直鎖状又は分岐状のアルキレン基を表す。 R 52 and R 53 , R 52 and R 54 , R 53 and R 54 may form a ring, and in the case of forming a ring, R 52 , R 53 and R 54 each have 1 to 18 carbon atoms, Preferably it represents 1-10 linear or branched alkylene groups.
上記式(VI)としては、具体的にはt−ブトキシカルボニル基、t−ブトキシカルボニルメチル基、t−アミロキシカルボニル基、t−アミロキシカルボニルメチル基、1,1−ジエチルプロピルオキシカルボニル基、1,1−ジエチルプロピルオキシカルボニルメチル基、1−エチルシクロペンチルオキシカルボニル基、1−エチルシクロペンチルオキシカルボニルメチル基、1−エチル−2−シクロペンテニルオキシカルボニル基、1−エチル−2−シクロペンテニルオキシカルボニルメチル基、1−エトキシエトキシカルボニルメチル基、2−テトラヒドロピラニルオキシカルボニルメチル基、2−テトラヒドロフラニルオキシカルボニルメチル基等が例示できる。 Specific examples of the formula (VI) include a t-butoxycarbonyl group, a t-butoxycarbonylmethyl group, a t-amyloxycarbonyl group, a t-amyloxycarbonylmethyl group, a 1,1-diethylpropyloxycarbonyl group, 1,1-diethylpropyloxycarbonylmethyl group, 1-ethylcyclopentyloxycarbonyl group, 1-ethylcyclopentyloxycarbonylmethyl group, 1-ethyl-2-cyclopentenyloxycarbonyl group, 1-ethyl-2-cyclopentenyloxycarbonyl Examples thereof include a methyl group, 1-ethoxyethoxycarbonylmethyl group, 2-tetrahydropyranyloxycarbonylmethyl group, 2-tetrahydrofuranyloxycarbonylmethyl group and the like.
上記式(VII)で示される酸不安定基のうち直鎖状又は分岐状のものとしては、具体的には、メトキシメチル基、エトキシメチル基、n−プロポキシメチル基、n−ブトキシメチル基、イソプロポキシメチル基、t−ブトキシメチル基、1−メトキシ−エチル基、1−エトキシ−エチル基、1−メトキシ−プロピル基、1−メトキシ−ブチル基、1−エトキシ−プロピル基、1−エトキシ−プロピル基、1−n−プロポキシエチル基、1−n−プロポキシエチル基、1−n−プロポキシ−プロピル基、1−n―ブトキシ−ブチル基、1−n−プロポキシ−ブチル基、1−シクロペンチルオキシ−エチル基、1−シクロヘキシルオキシ−エチル基、2−メトキシ−2−プロピル基、2−エトキシ−2−プロピル基等を例示することができる。 Among the acid labile groups represented by the above formula (VII), as linear or branched ones, specifically, a methoxymethyl group, an ethoxymethyl group, an n-propoxymethyl group, an n-butoxymethyl group, Isopropoxymethyl group, t-butoxymethyl group, 1-methoxy-ethyl group, 1-ethoxy-ethyl group, 1-methoxy-propyl group, 1-methoxy-butyl group, 1-ethoxy-propyl group, 1-ethoxy- Propyl group, 1-n-propoxyethyl group, 1-n-propoxyethyl group, 1-n-propoxy-propyl group, 1-n-butoxy-butyl group, 1-n-propoxy-butyl group, 1-cyclopentyloxy -Ethyl group, 1-cyclohexyloxy-ethyl group, 2-methoxy-2-propyl group, 2-ethoxy-2-propyl group and the like can be exemplified.
上記式(VIII)で示される酸不安定基のうち環状のものとしては、具体的にはテトラヒドロフラン−2−イル基、2−メチルテトラヒドロフラン−2−イル基、テトラヒドロピラン−2−イル基、2−メチルテトラヒドロピラン−2−イル基等が例示できる。式(4)としては、1−エトキシ−エチル基、1−n−ブトキシ−エチル基、1−エトキシ−n−プロピル基が好ましい。 Specific examples of the acid labile group represented by the above formula (VIII) include cyclic tetrahydrofuran-2-yl group, 2-methyltetrahydrofuran-2-yl group, tetrahydropyran-2-yl group, 2 -A methyltetrahydropyran-2-yl group etc. can be illustrated. As the formula (4), a 1-ethoxy-ethyl group, a 1-n-butoxy-ethyl group, and a 1-ethoxy-n-propyl group are preferable.
式(VIII)においてR55、R56、R57は炭素数1〜20の直鎖状、分岐状もしくは環状のアルキル基等の1価炭化水素基であり、酸素原子、硫黄原子、窒素原子等のヘテロ原子、フッ素原子等を含んでもよく、R55とR56、R55とR57、R56とR57とは互いに結合して環を結合してもよい。 In the formula (VIII), R 55 , R 56 , and R 57 are monovalent hydrocarbon groups such as a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, such as an oxygen atom, a sulfur atom, and a nitrogen atom. Hetero atoms, fluorine atoms and the like, and R 55 and R 56 , R 55 and R 57 , and R 56 and R 57 may be bonded to each other to form a ring.
式(VIII)に示される三級アルキル基としては、t−ブチル基、1,1−ジエチル−n−プロピル基、1−エチルノルボニル基、1−メチルシクロヘキシル基、1−エチルシクロペンチル基、2−(2−メチル)アダマンチル基、2−(2−エチル)アダマンチル基、tert−アミル基等を挙げることができる。 The tertiary alkyl group represented by the formula (VIII) includes t-butyl group, 1,1-diethyl-n-propyl group, 1-ethylnorbornyl group, 1-methylcyclohexyl group, 1-ethylcyclopentyl group, 2 -(2-Methyl) adamantyl group, 2- (2-ethyl) adamantyl group, tert-amyl group and the like can be mentioned.
また、式(VII)で表される三級アルキル基としては、下記に示す官能基を具体的に例示することができる。 Moreover, as a tertiary alkyl group represented by Formula (VII), the functional group shown below can be illustrated concretely.
ここで、R61、R64は炭素数1〜6の直鎖状、分岐状又は環状のアルキル基を示し、具体的にはメチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、n−ペンチル基、n−ヘキシル基、シクロプロピル基、シクロプロピルメチル基等を例示できる。R62は水素原子、炭素数1〜6のヘテロ原子を含んでもよい1価炭化水素基、又は炭素数1〜6のヘテロ原子を介してもよいアルキル基等の1価炭化水素基を示す。ヘテロ原子としては、酸素原子、硫黄原子、窒素原子を挙げることができ、−OH、−OR(Rは炭素数1〜20、特に1〜16のアルキル基、以下同じ)、−O−、−S−、−S(=O)−、−NH2、−NHR、−NR2、−NH−、−NR−として含有又は介在することができる。 Here, R 61 and R 64 represent a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, specifically a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, Examples include sec-butyl group, n-pentyl group, n-hexyl group, cyclopropyl group, cyclopropylmethyl group and the like. R 62 is a monovalent hydrocarbon radical such as a hydrogen atom, it contains a heteroatom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, or an alkyl group which may through a hetero atom having 1 to 6 carbon atoms. Examples of the hetero atom include an oxygen atom, a sulfur atom, and a nitrogen atom, and —OH, —OR (R is an alkyl group having 1 to 20 carbon atoms, particularly 1 to 16 carbon atoms, the same applies hereinafter), —O—, — S -, - S (= O ) -, - NH 2, -NHR, -NR 2, -NH -, - can contain or intervening as NR-.
R63としては、水素原子、又は炭素数1〜20、特に1〜16のアルキル基、ヒドロキシアルキル基、アルコキシアルキル基、アルコキシ基又はアルコキシアルキル基などを挙げることができ、これらは直鎖状、分岐状、環状のいずれでもい。具体的には、メチル基、ヒドロキシメチル基、エチル基、ヒドロキシエチル基、プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、n−ペンチル基、n−ヘキシル基、メトキシ基、メトキシメトキシ基、エトキシ基、tert−ブトキシ基等を例示できる。 Examples of R 63 include a hydrogen atom, or an alkyl group having 1 to 20 carbon atoms, particularly 1 to 16 carbon atoms, a hydroxyalkyl group, an alkoxyalkyl group, an alkoxy group, or an alkoxyalkyl group. It can be either branched or annular. Specifically, methyl group, hydroxymethyl group, ethyl group, hydroxyethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, n-pentyl group, n-hexyl group, methoxy group, methoxymethoxy Group, ethoxy group, tert-butoxy group and the like.
また、R41の酸不安定基として用いられる各アルキル基がそれぞれ炭素数1〜6のトリアルキルシリル基としてはトリメチルシリル基、トリエチルシリル基、tert−ブチルジメチルシリル基等が挙げられる。 Examples of the trialkylsilyl group in which each alkyl group used as the acid labile group of R 41 has 1 to 6 carbon atoms include a trimethylsilyl group, a triethylsilyl group, and a tert-butyldimethylsilyl group.
R41の酸不安定基として用いられる炭素数4〜20のオキソアルキル基としては、3−オキソシクロヘキシル基、下記式で示される基が挙げられる。 Examples of the oxoalkyl group having 4 to 20 carbon atoms used as the acid labile group for R 41 include a 3-oxocyclohexyl group and a group represented by the following formula.
更に、上記R41の酸不安定基は、下記式(IX)又は(X)で表されるアセタール架橋基であってもよい。 Furthermore, the acid labile group of R 41 may be an acetal bridging group represented by the following formula (IX) or (X).
式中、R71、R72は水素原子又は炭素数1〜8の直鎖状、分岐状もしくは環状のアルキル基を示す。又は、R71とR72は結合して環を形成してもよく、環を形成する場合にはR71、R72は炭素数1〜8の直鎖状又は分岐状のアルキレン基を示す。R73は炭素数1〜10の直鎖状、分岐状又は環状のアルキレン基、eは1〜7の整数、f、gは0又は1〜10の整数である。Aは、(e+1)価の炭素数1〜50の脂肪族もしくは脂環式飽和炭化水素基、芳香族炭化水素基又はヘテロ環基を示し、これらの基はヘテロ原子を介在してもよく、又はその炭素原子に結合する水素原子の一部が水酸基、カルボキシル基、カルボニル基又はフッ素原子によって置換されていてもよい。Bは−CO−O−、−NHCO−O−又は−NHCONH−を示す。 In formula, R71 , R72 shows a hydrogen atom or a C1-C8 linear, branched or cyclic alkyl group. Alternatively, R 71 and R 72 may be bonded to form a ring, and when forming a ring, R 71 and R 72 represent a linear or branched alkylene group having 1 to 8 carbon atoms. R 73 is a linear, branched or cyclic alkylene group having 1 to 10 carbon atoms, e is an integer of 1 to 7, and f and g are 0 or an integer of 1 to 10. A represents an (e + 1) -valent aliphatic or alicyclic saturated hydrocarbon group having 1 to 50 carbon atoms, an aromatic hydrocarbon group or a heterocyclic group, and these groups may intervene a hetero atom, Alternatively, a part of hydrogen atoms bonded to the carbon atom may be substituted with a hydroxyl group, a carboxyl group, a carbonyl group, or a fluorine atom. B represents —CO—O—, —NHCO—O— or —NHCONH—.
式(IX)、(X)に示される架橋型アセタールは、具体的には下記式のものを例示することができる。 Specific examples of the crosslinked acetal represented by the formulas (IX) and (X) include the following formulas.
式(V)で表される官能基を有する繰り返し単位(IV)として、具体的には、下記単量体を重合して得られる繰り返し単位を例示することができる。 Specific examples of the repeating unit (IV) having a functional group represented by the formula (V) include repeating units obtained by polymerizing the following monomers.
スチレン、α−メチルスチレン、フルオロスチレン、1,1−ジフェニルエチレン、スチルベン、4−ヒドロキシスチレン、4−ヒドロキシ−α−メチルスチレン、4−ヒドロキシ−3−メチル−スチレン、4−t−ブトキシ−スチレン、4−テトラヒドロピラニルオキシ−スチレン、4−フェノキシエトキシ−スチレン、4−トリメチルシリルオキシ−スチレン、4−t−ブトキシカルボニルオキシ−スチレン、4−t−ブトキシカルボニルメトキシ−スチレン、2,3−ジフルオロ−4−ヒドロキシスチレン、2,3−ジフルオロ−4−t−ブトキシ−スチレン、2,6−ジフルオロ−4−ヒドロキシ−スチレン、2,6−ジフルオロ−4−t−ブトキシ−スチレン、3,5−ジフルオロ−4−ヒドロキシ−スチレン、3,5−ジフルオロ−4−t−ブトキシ−スチレン、2,3,5,6−テトラフルオロ−4−ヒドロキシ−スチレン、2,3,5,6−テトラフルオロ−4−t−ブトキシ−スチレン、2−トリフルオロメチル−4−ヒドロキシ−スチレン、2−トリフルオロメチル−4−t−ブトキシ−スチレン、2−トリフルオロメチル−6−フロロ−4−ヒドロキシ−スチレン、2−トリフルオロメチル−6−フロロ−4−t−ブトキシ−スチレン、3−トリフルオロメチル−5−フロロ−4−ヒドロキシ−スチレン、3−トリフルオロメチル−5−フロロ−4−t−ブトキシ−スチレン、4−(1−エトキシエトキシ)−スチレン、4−(2−ヒドロキシ−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル)−スチレン、4−(2−エトキシメトキシ−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル)−スチレン、2,3−ジフルオロ−4−ヒドロキシスチレン、2,3−ジフルオロ−4−t−ブトキシ−α−フルオロ−スチレン、2,6−ジフルオロ−4−ヒドロキシ−α−フルオロ−スチレン、2,6−ジフルオロ−4−t−ブトキシ−α−フルオロ−スチレン、3,5−ジフルオロ−4−ヒドロキシ−α−フルオロ−スチレン、3,5−ジフルオロ−4−t−ブトキシ−α−フルオロ−スチレン、2,3,5,6−テトラフルオロ−4−ヒドロキシ−α−フルオロ−スチレン、2,3,5,6−テトラフルオロ−4−t−ブトキシ−α−フルオロ−スチレン、2−トリフルオロメチル−4−ヒドロキシ−α−フルオロ−スチレン、2−トリフルオロメチル−4−t−ブトキシ−α−フルオロ−スチレン、2−トリフルオロメチル−6−フルオロ−4−ヒドロキシ−α−フルオロ−スチレン、2−トリフルオロメチル−6−フルオロ−4−t−ブトキシ−α−フルオロ−スチレン、3−トリフルオロメチル−5−フルオロ−4−ヒドロキシ−α−フルオロ−スチレン、3−トリフルオロメチル−5−フルオロ−4−t−ブトキシ−α−フルオロ−スチレン、4−(1−エトキシエトキシ)−α−メチル−スチレン、4−(2−ヒドロキシ−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル)−α−フルオロ−スチレン、4−(2−エトキシメトキシ−1,1,1,3,3,3−ヘキサフルオロ−2−プロピル)−α−フルオロ−スチレン等。 Styrene, α-methylstyrene, fluorostyrene, 1,1-diphenylethylene, stilbene, 4-hydroxystyrene, 4-hydroxy-α-methylstyrene, 4-hydroxy-3-methyl-styrene, 4-t-butoxy-styrene 4-tetrahydropyranyloxy-styrene, 4-phenoxyethoxy-styrene, 4-trimethylsilyloxy-styrene, 4-t-butoxycarbonyloxy-styrene, 4-t-butoxycarbonylmethoxy-styrene, 2,3-difluoro- 4-hydroxystyrene, 2,3-difluoro-4-t-butoxy-styrene, 2,6-difluoro-4-hydroxy-styrene, 2,6-difluoro-4-t-butoxy-styrene, 3,5-difluoro -4-hydroxy-styrene, 3,5-difluoro -4-tert-butoxy-styrene, 2,3,5,6-tetrafluoro-4-hydroxy-styrene, 2,3,5,6-tetrafluoro-4-tert-butoxy-styrene, 2-trifluoromethyl -4-hydroxy-styrene, 2-trifluoromethyl-4-t-butoxy-styrene, 2-trifluoromethyl-6-fluoro-4-hydroxy-styrene, 2-trifluoromethyl-6-fluoro-4-t -Butoxy-styrene, 3-trifluoromethyl-5-fluoro-4-hydroxy-styrene, 3-trifluoromethyl-5-fluoro-4-tert-butoxy-styrene, 4- (1-ethoxyethoxy) -styrene, 4- (2-hydroxy-1,1,1,3,3,3-hexafluoro-2-propyl) -styrene, 4- (2-ethoxymethoxy-1,1, , 3,3,3-hexafluoro-2-propyl) -styrene, 2,3-difluoro-4-hydroxystyrene, 2,3-difluoro-4-tert-butoxy-α-fluoro-styrene, 2,6- Difluoro-4-hydroxy-α-fluoro-styrene, 2,6-difluoro-4-t-butoxy-α-fluoro-styrene, 3,5-difluoro-4-hydroxy-α-fluoro-styrene, 3,5- Difluoro-4-t-butoxy-α-fluoro-styrene, 2,3,5,6-tetrafluoro-4-hydroxy-α-fluoro-styrene, 2,3,5,6-tetrafluoro-4-t- Butoxy-α-fluoro-styrene, 2-trifluoromethyl-4-hydroxy-α-fluoro-styrene, 2-trifluoromethyl-4-t-butoxy-α-fluoro Styrene, 2-trifluoromethyl-6-fluoro-4-hydroxy-α-fluoro-styrene, 2-trifluoromethyl-6-fluoro-4-tert-butoxy-α-fluoro-styrene, 3-trifluoromethyl- 5-fluoro-4-hydroxy-α-fluoro-styrene, 3-trifluoromethyl-5-fluoro-4-t-butoxy-α-fluoro-styrene, 4- (1-ethoxyethoxy) -α-methyl-styrene 4- (2-hydroxy-1,1,1,3,3,3-hexafluoro-2-propyl) -α-fluoro-styrene, 4- (2-ethoxymethoxy-1,1,1,3, 3,3-hexafluoro-2-propyl) -α-fluoro-styrene and the like.
さらに、R34が、CO2R35基の場合において、R35は、R4で例示した置換基と同様の置換基を例示することができる。また、この場合、R31〜R33の組み合わせてとして、下記式に示すような組み合わせを好ましく用いることができる。(下記化合物を重合したとき得られ繰り返し単位を表す。) Furthermore, when R 34 is a CO 2 R 35 group, R 35 can be exemplified by the same substituents as those exemplified for R 4 . In this case, as a combination of R 31 to R 33, a combination as shown in the following formula can be preferably used. (Repeated unit obtained when polymerizing the following compounds.)
CO2R35基を有する繰り返し単位として、具体的には、アクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸アミル、アクリル酸シクロヘキシル、アクリル酸エチルヘキシル、アクリル酸オクチル、アクリル酸−t−オクチル、クロルエチルアクリレート、2−エトキシエチルアクリレート、2,2−ジメチル−3−エトキシプロピルアクリレート、5−エトキシペンチルアクリレート、1−メトキシエチルアクリレート、1−エトキシエチルアクリレート、1−メトキシプロピルアクリレート、1−メチル−1−メトキシエチルアクリレート、1−(イソプロポキシ)エチルアクリレート、ベンジルアクリレート、メトキシベンジルアクリレート、フルフリルアクリレート、テトラヒドロフルフリルアクリレート等のアクリル酸エステル類、
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。
Specific examples of the repeating unit having a CO 2 R 35 group include methyl acrylate, ethyl acrylate, propyl acrylate, amyl acrylate, cyclohexyl acrylate, ethyl hexyl acrylate, octyl acrylate, and tert-octyl acrylate. , Chloroethyl acrylate, 2-ethoxyethyl acrylate, 2,2-dimethyl-3-ethoxypropyl acrylate, 5-ethoxypentyl acrylate, 1-methoxyethyl acrylate, 1-ethoxyethyl acrylate, 1-methoxypropyl acrylate, 1-methyl -1-methoxyethyl acrylate, 1- (isopropoxy) ethyl acrylate, benzyl acrylate, methoxybenzyl acrylate, furfuryl acrylate, tetrahydrofurfuryl acrylate, etc. Acrylic acid esters,
Methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, amyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, chlorobenzyl methacrylate, octyl methacrylate, 2-ethoxyethyl methacrylate, 4-methoxybutyl methacrylate, 5-methoxypentyl methacrylate, 2 , 2-dimethyl-3-ethoxypropyl methacrylate, 1-methoxyethyl methacrylate, 1-ethoxyethyl methacrylate, 1-methoxypropyl methacrylate, 1-methyl-1-methoxyethyl methacrylate, 1- (isopropoxy) ethyl methacrylate, furfuryl Methacrylate, tetrahydrofurfuryl methacrylate, etc. Methacrylic acid esters, methyl crotonate, ethyl crotonate, propyl crotonate, amyl crotonate, cyclohexyl crotonate, ethyl hexyl crotonate, octyl crotonate, crotonic acid-t-octyl, chloroethyl crotonate, 2-ethoxyethyl crotonate 2,2-dimethyl-3-ethoxypropyl crotonate, 5-ethoxypentyl crotonate, 1-methoxyethyl crotonate, 1-ethoxyethyl crotonate, 1-methoxypropyl crotonate, 1-methyl-1-methoxy Crotonic acid esters such as ethyl crotonate, 1- (isopropoxy) ethyl crotonate, benzyl crotonate, methoxybenzyl crotonate, furfuryl crotonate, tetrahydrofurfuryl crotonate, etc. Dimethyl citrate, diethyl itaconate, dipropyl itaconate, diamyl itaconate, dicyclohexyl itaconate, bis (ethylhexyl) itaconate, dioctyl itaconate, di-t-octyl itaconate, bis (chloroethyl) itaconate, bis (2- Ethoxyethyl) itaconate, bis (2,2-dimethyl-3-ethoxypropyl) itaconate, bis (5-ethoxypentyl) itaconate, bis (1-methoxyethyl) itaconate, bis (1-ethoxyethyl) itaconate, bis (1 -Methoxypropyl) itaconate, bis (1-methyl-1-methoxyethyl) itaconate, bis (1- (isopropoxy) ethyl) itaconate, dibenzylitaconate, bis (methoxybenzyl) itaconate, diflufuryl Examples thereof include repeating units derived from itaconic acid esters such as taconate and ditetrahydrofurfururitaconate. Furthermore, the repeating unit represented by a following formula can be illustrated.
さらに式(I)で表される繰り返し単位以外のくり返し単位として、式(XI)で表される化合物を例示することができる。 Furthermore, as a repeating unit other than the repeating unit represented by the formula (I), a compound represented by the formula (XI) can be exemplified.
式(XI)中、R81、及びR82はそれぞれ独立に、水素原子、フッ素原子、C1〜C20の炭化水素基、ヘテロ環基、シアノ基、ニトロ基、C(=O)R4基、S(O)nR4基、P(=O)(R4)2基、M(R4)3基を表し、具体的には、R1で例示した置換基と同様の置換基を例示することができる。 In the formula (XI), R 81 and R 82 each independently represent a hydrogen atom, a fluorine atom, a C1-C20 hydrocarbon group, a heterocyclic group, a cyano group, a nitro group, a C (═O) R 4 group, Represents an S (O) nR 4 group, a P (═O) (R 4 ) 2 group, and an M (R 4 ) 3 group. Specifically, the same substituents as those exemplified for R 1 are exemplified. be able to.
本発明における式(I)で表される繰り返し単位を有する重合体は、先に記載したように、式(I)で表される繰り返し単位のみからなる重合体、並びに式(I)で表される繰り返し単位及び式(I)で表される繰り返し単位以外の繰り返し単位からなる重合体を意味しており、式(I)で表され繰り返し単位とそれ以外の繰り返し単位の重合形式は特に限定されず、ランダム重合形式、ブロック重合形式、部分ブロック重合形式、交互重合形式のいずれの形式をもとることができる。 The polymer having the repeating unit represented by the formula (I) in the present invention is represented by the polymer consisting only of the repeating unit represented by the formula (I) and the formula (I) as described above. Means a polymer comprising a repeating unit other than the repeating unit represented by formula (I), and the polymerization mode of the repeating unit represented by formula (I) and the other repeating unit is particularly limited. Any of random polymerization, block polymerization, partial block polymerization, and alternating polymerization can be used.
また、式(I)で表され繰り返し単位とそれ以外の繰り返し単位の混合比率は特に限定されず、モル比で、99/1〜1/99の範囲で任意に設定することができる。 Moreover, the mixing ratio of the repeating unit represented by the formula (I) and the other repeating units is not particularly limited, and can be arbitrarily set in a molar ratio of 99/1 to 1/99.
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は、特に制限されないが、レジスト等に用いる場合に耐エッチング性、アルカリ溶解性等を考慮すると、2,000〜50,000の範囲が好ましい。また重量平均分子量(Mw)と数平均分子量(Mn)の比である分子量分布も、特に制限はされないが、レジスト等の微細加工を行う上では1.01〜3.00の範囲、さらには1.01〜1.50の範囲が好ましい。 The number average molecular weight of the polymer having a repeating unit represented by the formula (I) is not particularly limited. However, when used for a resist or the like, in consideration of etching resistance, alkali solubility, etc., 2,000 to 50,000 The range of is preferable. The molecular weight distribution, which is the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn), is not particularly limited, but is in the range of 1.01 to 3.00, 1 A range of .01 to 1.50 is preferred.
式(I)で表される繰り返し単位を有する重合体の製造方法として、具体的には、下記式(XII)で表されるケテンおよび式(XIII)で表されるアルデヒドを、アニオン重合開始剤存在下、アニオン重合を行う方法を例示することができる。 As a method for producing a polymer having a repeating unit represented by the formula (I), specifically, a ketene represented by the following formula (XII) and an aldehyde represented by the formula (XIII) are converted into an anionic polymerization initiator. A method for anionic polymerization in the presence can be exemplified.
式中、R91はR1、R92はR2、R93はR3にそれぞれ対応しており、アニオン重合を行う上で、障害となる置換基、例えば、活性水素原子を有する置換基、アニオン重合開始剤と反応性を有する置換基等を除外した置換基を表す。 In the formula, R 91 corresponds to R 1 , R 92 corresponds to R 2 , and R 93 corresponds to R 3 , respectively, and a substituent that hinders anionic polymerization, such as a substituent having an active hydrogen atom, The substituent which excluded the substituent etc. which are reactive with an anionic polymerization initiator is represented.
アニオン重合に用いられる溶媒は、重合反応に関与せず、かつ重合体と相溶性のある極性溶媒であれば、特に制限されず、具体的には、n−ヘキサン、n−ヘプタン等の脂肪族炭化水素類、シクロヘキサン、シクロペンタン等の脂環族炭化水素類、ベンゼン、トルエン等の芳香族炭化水素類、ジエチルエーテル、テトラヒドロフラン(THF)、ジオキサン等のエーテル類の他、アニソール、ヘキサメチルホスホルアミド等のアニオン重合において通常使用される有機溶媒を挙げることができる。また、これらの溶媒は、1種単独で、または2種以上の混合溶媒として用いることができる。 The solvent used for anionic polymerization is not particularly limited as long as it is a polar solvent that does not participate in the polymerization reaction and is compatible with the polymer. Specifically, aliphatic solvents such as n-hexane and n-heptane are used. Hydrocarbons, alicyclic hydrocarbons such as cyclohexane and cyclopentane, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether, tetrahydrofuran (THF) and dioxane, as well as anisole and hexamethyl phosphor The organic solvent normally used in anionic polymerization, such as amide, can be mentioned. Moreover, these solvent can be used individually by 1 type or as a 2 or more types of mixed solvent.
アニオン重合開始剤として、アルカリ金属又は有機アルカリ金属を例示することができ、アルカリ金属としては、リチウム、ナトリウム、カリウム、セシウム、ナトリウム−カリウム合金等を例示することができ、有機アルカリ金属としては、上記アルカリ金属のアルキル化物、アリル化物、アリール化物等を使用することができ、具体的には、エチルリチウム、n−ブチルリチウム、sec−ブチルリチウム、t−ブチルリチウム、エチルナトリウム、リチウムビフェニル、リチウムナフタレン、リチウムトリフェニル、ナトリウムナフタレン、カリウムナフタレン、α−メチルスチレンナトリウムジアニオン、1,1−ジフェニルヘキシルリチウム、1,1−ジフェニル−3−メチルペンチルリチウム、1,1−ジフェニルメチルカリウム、1,4−ジリチオ−2−ブテン、1,6−ジリチオヘキサン、ポリスチリルリチウム、クミルカリウム、クミルセシウム等を挙げることができ、これらの化合物は、1種単独で、または2種以上を混合して用いることができる。 Examples of the anionic polymerization initiator include alkali metals or organic alkali metals. Examples of the alkali metals include lithium, sodium, potassium, cesium, sodium-potassium alloys, and the like. Alkylated products, allylated products, arylated products and the like of the above alkali metals can be used. Specifically, ethyllithium, n-butyllithium, sec-butyllithium, t-butyllithium, ethylsodium, lithium biphenyl, lithium Naphthalene, lithium triphenyl, sodium naphthalene, potassium naphthalene, α-methylstyrene sodium dianion, 1,1-diphenylhexyl lithium, 1,1-diphenyl-3-methylpentyl lithium, 1,1-diphenylmethyl potassium 1,4-dilithio-2-butene, 1,6-dilithiohexane, polystyryllithium, cumylpotassium, cumylcesium and the like. These compounds may be used alone or in combination of two or more. Can be used.
反応は、通常、アニオン重合開始剤に、式(XII)および(XIII)で表される化合物を添加し、アニオンリビング重合を行う。これらの一連の反応は、アルゴンまたは窒素等の不活性ガス下、もしくは高真空下、−100〜0℃、好ましくは、−70〜−20℃の範囲で行われる。用いる式(XII)で表されるケテンと式(XIII)で表されるアルデヒドのモル比は特に制限されないが、99/1〜50/50の範囲で用いるのが好ましい。また、先にも述べたように、式(XII)で表されるケテンおよび式(XIII)で表されるアルデヒドは、それぞれ1種単独で、または2種以上を混合して用いることができる。 In the reaction, compounds represented by the formulas (XII) and (XIII) are usually added to an anionic polymerization initiator, and anionic living polymerization is performed. These series of reactions are carried out in the range of −100 to 0 ° C., preferably −70 to −20 ° C. under an inert gas such as argon or nitrogen, or under high vacuum. The molar ratio of the ketene represented by the formula (XII) to be used and the aldehyde represented by the formula (XIII) is not particularly limited, but is preferably in the range of 99/1 to 50/50. Further, as described above, the ketene represented by the formula (XII) and the aldehyde represented by the formula (XIII) can be used singly or in combination of two or more.
また、R3が式(II)で表される置換基である重合体中、R5が水素原子である化合物は、水素原子以外の官能基を有する化合物で重合を行い、その官能基を脱離させることにより得ることができ、その際、反応を制御することにより、前記官能基の一部のみを脱離させることもできる。例えば、酸に対して不安定なフェノール性水酸基の保護基を一部また全部脱離させる反応は、前記重合反応で例示した溶媒の他、メタノール、エタノール等のアルコール類、アセトン、メチルエチルケトン等のケトン類、メチルセロソルブ、エチルセロソルブ等の多価アルコール誘導体類、水などの一種単独又は二種以上の混合溶媒の存在下、塩酸、硫酸、塩化水素ガス、臭化水素酸、p−トルエンスルホン酸、トリフロロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸、一般式 XHSO4(式中、XはLi、Na、K等のアルカリ金属を表す)で示される重硫酸塩などの酸性試剤を触媒として、通常、室温〜150℃の温度で行われる。また、保護基としてシリル基を用いた場合には、四級アンモニウムフルオリド等のフッ素アニオン化合物をも用いることができる。 In the polymer in which R 3 is a substituent represented by the formula (II), a compound in which R 5 is a hydrogen atom is polymerized with a compound having a functional group other than a hydrogen atom, and the functional group is removed. In this case, only part of the functional group can be eliminated by controlling the reaction. For example, the reaction for partially or completely removing the protecting group of the phenolic hydroxyl group that is unstable to acids includes the solvents exemplified in the polymerization reaction, alcohols such as methanol and ethanol, and ketones such as acetone and methyl ethyl ketone. , Polyhydric alcohol derivatives such as methyl cellosolve, ethyl cellosolve, one or more kinds of mixed solvents such as water, hydrochloric acid, sulfuric acid, hydrogen chloride gas, hydrobromic acid, p-toluenesulfonic acid, Trichloroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, general formula XHSO 4 (wherein X represents an alkali metal such as Li, Na, K, etc.) and an acid reagent such as bisulfate are usually used as catalysts. It is carried out at a temperature between room temperature and 150 ° C. Further, when a silyl group is used as a protecting group, a fluorine anion compound such as quaternary ammonium fluoride can also be used.
用いる酸性試剤の量は、触媒量で十分であるが、通常各ユニットのモル分率、各ユニットの分子量よりポリマー全体の平均分子量を求め、ポリマーの全重量、平均分子量、及びモル分率より各ユニットのモル数を求め、アルコキシ基(OR5基)のモル数に対して0.1〜3当量、好ましくは0.1〜1当量の範囲である。 The amount of the acidic reagent to be used is sufficient as the catalyst amount, but usually the average molecular weight of the whole polymer is obtained from the molar fraction of each unit and the molecular weight of each unit, and each of the total weight, average molecular weight, and molar fraction of each polymer is determined. The number of moles of the unit is determined, and is in the range of 0.1 to 3 equivalents, preferably 0.1 to 1 equivalents relative to the number of moles of the alkoxy group (OR 5 group).
また、上記のようにして得られた水酸基部分に別の官能基を導入することもできる。前記した操作は、R3の置換基を例としてしてあげて説明したが、R1、R2上のOR5と同様の置換基においても行うことができる。 Moreover, another functional group can also be introduce | transduced into the hydroxyl part obtained as mentioned above. The above-described operation has been described by taking the substituent of R 3 as an example, but it can also be performed on the same substituent as OR 5 on R 1 and R 2 .
式(I)で表される繰り返し単位を有する重合体は、実施例において述べるように酸により容易に主鎖が開裂する性質を有する。本発明における組成物においては、アルカリ可溶性樹脂と混合して用いることにより、コントラストを鮮明にするための溶解阻止剤として用いることができる。 The polymer having a repeating unit represented by the formula (I) has a property that the main chain is easily cleaved by an acid as described in Examples. In the composition in this invention, it can be used as a dissolution inhibitor for making contrast clear by mixing with alkali-soluble resin.
式(I)で表される繰り返し単位を有する重合体の配合量は、アルカリ可溶性重合体100部(重量部、以下同じ)に対して0〜50部、好ましくは5〜50部、より好ましくは10〜30部であり、単独又は2種以上を混合して使用できる。配合量が5部に満たないと解像性の向上がない場合があり、50部を超えるとパターンの膜減りが生じ、解像度が低下する場合がある。
(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。
The blending amount of the polymer having a repeating unit represented by formula (I) is 0 to 50 parts, preferably 5 to 50 parts, more preferably 100 parts by weight of alkali-soluble polymer (parts by weight, hereinafter the same). It is 10-30 parts, and can be used individually or in mixture of 2 or more types. If the blending amount is less than 5 parts, the resolution may not be improved, and if it exceeds 50 parts, the film thickness of the pattern may be reduced and the resolution may be lowered.
(III) Acid generator The acid generator used in the present invention is not limited as long as it is a compound capable of generating an acid upon irradiation with radiation and does not adversely affect the formation of a resist pattern, but particularly around 248.4 nm. The light transmittance of the resist composition is high and the transparency of the resist composition can be maintained, or the light transparency is increased by exposure and the transparency of the resist composition can be maintained, or the acid generation efficiency is high, so a small amount can be added. An acid generator that exhibits an effect is preferred. Specific examples of particularly preferable acid generators include compounds represented by the following formula (XIV), formula (XV), formula (XVI), formula (XVII), and formula (XVIII). .
(式中、R100及びR101は夫々独立して炭素数1〜6の直鎖状、分枝状又は環状のアルキル基、又はアラルキル基を表し、Wはスルホニル基又はカルボニル基を表す。) (Wherein R 100 and R 101 each independently represents a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, or an aralkyl group, and W represents a sulfonyl group or a carbonyl group.)
(式中、R103及びR104は夫々独立して水素原子、ハロゲン原子又は炭素数1〜4のアルキル基を表し、R105は炭素数1〜6の直鎖状、分枝状又は環状のアルキル基、アラルキル基、又は置換されていても良いフェニル基を表し、Vはスルホニル基又はカルボニル基を表す。) (In the formula, R 103 and R 104 each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms, and R 105 represents a linear, branched or cyclic group having 1 to 6 carbon atoms. Represents an alkyl group, an aralkyl group, or an optionally substituted phenyl group, and V represents a sulfonyl group or a carbonyl group.)
(式中、R106、R107及びR108は夫々独立して水素原子、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、又はt-ブトキシカルボニルオキシ基を表し、R109は炭素数1〜8の含フッ素アルキル基、置換されていても良いフェニル基、又は10−カンファー基を表し、Yは硫黄原子またはヨウ素原子を表し、Yがヨウ素原子の場合、zは0を表し、硫黄原子の場合、zは1を表す。) (Wherein, R 106, R 107 and R 108 are independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a t- butoxycarbonyl group, R 109 Represents a fluorine-containing alkyl group having 1 to 8 carbon atoms, an optionally substituted phenyl group, or a 10-camphor group, Y represents a sulfur atom or an iodine atom, and when Y is an iodine atom, z represents 0. And z represents 1 in the case of a sulfur atom.)
(式中、R110は炭素数1〜6のアルキル基、炭素数1〜8の含フッ素アルキル基、置換されていても良いフェニル基、又は10−カンファー基を表す。) (In the formula, R 110 represents an alkyl group having 1 to 6 carbon atoms, a fluorine-containing alkyl group having 1 to 8 carbon atoms, an optionally substituted phenyl group, or a 10-camphor group.)
(式中、R111及びR112は夫々独立して水素原子、メチル基、エチル基を表し、又、R111とR112とで芳香環基又は不飽和結合を有する有橋脂環炭化水素基を形成しても良く、R113は炭素数1〜6のアルキル基、炭素数1〜8の含フッ素アルキル基、置換されていても良いフェニル基、又は10−カンファー基を表す。)
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。
(In the formula, R 111 and R 112 each independently represent a hydrogen atom, a methyl group, or an ethyl group, and R 111 and R 112 have an aromatic ring group or a bridged alicyclic hydrocarbon group having an unsaturated bond. R 113 represents an alkyl group having 1 to 6 carbon atoms, a fluorine-containing alkyl group having 1 to 8 carbon atoms, an optionally substituted phenyl group, or a 10-camphor group.)
Specifically, preferred acid generators include those represented by formula (XIV) such as 1-cyclohexylsulfonyl-1- (1,1-dimethylethylsulfonyl) diazomethane, bis (1,1-dimethylethylsulfonyl). ) Diazomethane, bis (1-methylethylsulfonyl) diazomethane, bis (cyclohexylsulfonyl) diazomethane, 1-cyclohexylsulfonyl-1-cyclohexylcarbonyldiazomethane, 1-diazo-1-cyclohexylsulfonyl-3,3-dimethylbutan-2-one 1-diazo-1- (1,1-dimethylethylsulfonyl) -3,3-dimethylbutan-2-one and the like.
式(XV)で示される酸発生剤として具体的には、ビス(p−トルエンスルホニル)ジアゾメタン、ビス(2,4−ジメチルベンゼンスルホニル)ジアゾメタン、ビス(p−tert−ブチルフェニルスルホニル)ジアゾメタン、ビス(p-クロルベンゼンスルホニル)ジアゾメタン、メチルスルホニル−p−トルエンスルホニルジアゾメタン、シクロヘキシルスルホニル−p−トルエンスルホニルジアゾメタン、1−p−トルエンスルホニル−1−シクロヘキシルカルボニルジアゾメタン、1−ジアゾ−1−(p−トルエンスルホニル)−3,3−ジメチルブタン−2−オン等を例示することができる。 Specific examples of the acid generator represented by the formula (XV) include bis (p-toluenesulfonyl) diazomethane, bis (2,4-dimethylbenzenesulfonyl) diazomethane, bis (p-tert-butylphenylsulfonyl) diazomethane, bis (P-chlorobenzenesulfonyl) diazomethane, methylsulfonyl-p-toluenesulfonyldiazomethane, cyclohexylsulfonyl-p-toluenesulfonyldiazomethane, 1-p-toluenesulfonyl-1-cyclohexylcarbonyldiazomethane, 1-diazo-1- (p-toluene) Examples include sulfonyl) -3,3-dimethylbutan-2-one and the like.
式(XVI)で示される酸発生剤として具体的には、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、トリフェニルスルホニウム・パーフルオロブタンスルホネート、トリフェニルスルホニウム・パーフルオロオクタンスルホネート、トリフェニルスルホニウム・p−トルエンスルホネート、トリフェニルスルホニウム・10−カンファースルホネート、ジフェニル−p−トリルスルホニウム・トリフルオロメタンスルホネート、ジフェニル-p-トリルスルホニウム・パーフルオロブタンスルホネート、ジフェニル−p−トリルスルホニウム・パーフルオロオクタンスルホネート、ジフェニル−p−トリルスルホニウム・p-トルエンスルホネート、ジフェニル−p−トリルスルホニウム・10−カンファースルホネート、ジフェニル−p−tert−ブチル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、ジフェニル−p−tert−ブチルフェニルスルホニウム・パーフルオロブタンスルホネート、ジフェニル−p−tert−ブチルフェニルスルホニウム・パーフルオロオクタンスルホネート、ジフェニル−p−tert−ブチルフェニルスルホニウム・p−トルエンスルホネート、ジフェニル−p−tert−ブチルフェニルスルホニウム・10−カンファースルホネート、ジフェニル−p−tert−ブチルフェニルスルホニウム・p−フルオロベンゼンスルホネート、ジフェニル−p−シクロヘキシル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、ジフェニル−p−シクロヘキシルフェニルスルホニウム・パーフルオロブタンスルホネート、ジフェニル−p−シクロヘキシルフェニルスルホニウム・パーフルオロオクタンスルホネート、ジフェニル−p−シクロヘキシルフェニルスルホニウム・p−トルエンスルホネート、ジフェニル−p−tert−ブトキシ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、ジフェニル−p−tert−ブトキシフェニルスルホニウム・パーフルオロブタンスルホネート、ジフェニル−p−tert−ブトキシフェニルスルホニウム・パーフルオロオクタンスルホネート、ジフェニル−p−tert−ブトキシフェニルスルホニウム・p−トルエンスルホネート、ジフェニル−p−tert−ブトキシカルボニルオキシフェニルスルホニウム・パーフルオロオクタンスルホネート、ジフェニル−p−tert−ブトキシカルボニルオキシフェニルスルホニウム・10−カンファースルホネート、ジフェニル−p−tert−ブトキシカルボニルオキシフェニルスルホニウム・p−トルエンスルホネート、4,4’−ジ−tert−ブチルジフェニルヨードニウム・10−カンファースルホネート等を例示することができる。 Specific examples of the acid generator represented by the formula (XVI) include triphenylsulfonium / trifluoromethanesulfonate, triphenylsulfonium / perfluorobutanesulfonate, triphenylsulfonium / perfluorooctanesulfonate, triphenylsulfonium / p-toluenesulfonate. , Triphenylsulfonium ・ 10-camphorsulfonate, diphenyl-p-tolylsulfonium ・ trifluoromethanesulfonate, diphenyl-p-tolylsulfonium ・ perfluorobutanesulfonate, diphenyl-p-tolylsulfonium ・ perfluorooctanesulfonate, diphenyl-p-tolyl Sulfonium ・ p-toluenesulfonate, diphenyl-p-tolylsulfonium ・ 10-camphorsulfonate, diphenyl-p-tert- Butylphenylsulfonium / trifluoromethanesulfonate, diphenyl-p-tert-butylphenylsulfonium / perfluorobutanesulfonate, diphenyl-p-tert-butylphenylsulfonium / perfluorooctanesulfonate, diphenyl-p-tert-butylphenylsulfonium / p- Toluenesulfonate, diphenyl-p-tert-butylphenylsulfonium · 10-camphorsulfonate, diphenyl-p-tert-butylphenylsulfonium · p-fluorobenzenesulfonate, diphenyl-p-cyclohexylphenylsulfonium · trifluoromethanesulfonate, diphenyl-p- Cyclohexylphenylsulfonium perfluorobutanesulfonate, diphenyl-p-cyclohexylphenylsulfonium Fluorooctanesulfonate, diphenyl-p-cyclohexylphenylsulfonium / p-toluenesulfonate, diphenyl-p-tert-butoxyphenylsulfonium / trifluoromethanesulfonate, diphenyl-p-tert-butoxyphenylsulfonium / perfluorobutanesulfonate, diphenyl-p- tert-butoxyphenylsulfonium / perfluorooctanesulfonate, diphenyl-p-tert-butoxyphenylsulfonium / p-toluenesulfonate, diphenyl-p-tert-butoxycarbonyloxyphenylsulfonium / perfluorooctanesulfonate, diphenyl-p-tert-butoxy Carbonyloxyphenylsulfonium ・ 10-camphorsulfonate, diphenyl-p-tert-butoxycarbonyloxyphene Rusuruhoniumu-p-toluenesulfonate can be exemplified 4,4'--tert- butyl diphenyl iodonium-10-camphorsulfonate, and the like.
式(XVII)で示される酸発生剤として具体的には、1,2,3−トリス−メタンスルホニルオキシベンゼン、1,2,3−トリス−トリフルオロメタンスルホニルオキシベンゼン、1,2,3−トリス−パーフルオロオクタンスルホニルオキシベンゼン、1,2,3−トリス−パーフルオロブタンスルホニルオキシベンゼン、1,2,3−トリス−p−トルエンスルホニルオキシベンゼン、1,2,3−トリス−10−カンファースルホニルオキシベンゼン、1,2,3−トリス−トリフルオロアセチルオキシベンゼン、1,2,4−トリス−メタンスルホニルオキシベンゼン、1,2,4−トリス−トリフルオロメタンスルホニルオキシベンゼン、1,2,4−トリス−3−トリス−パーフルオロオクタンスルホニルオキシベンゼン、1,2,4−トリス− p−トルエンスルホニルオキシベンゼン、1,2,4−トリス−パーフルオロブタンスルホニルオキシベンゼン等を例示することができる。 Specific examples of the acid generator represented by the formula (XVII) include 1,2,3-tris-methanesulfonyloxybenzene, 1,2,3-tris-trifluoromethanesulfonyloxybenzene, 1,2,3-tris. -Perfluorooctanesulfonyloxybenzene, 1,2,3-tris-perfluorobutanesulfonyloxybenzene, 1,2,3-tris-p-toluenesulfonyloxybenzene, 1,2,3-tris-10-camphorsulfonyl Oxybenzene, 1,2,3-tris-trifluoroacetyloxybenzene, 1,2,4-tris-methanesulfonyloxybenzene, 1,2,4-tris-trifluoromethanesulfonyloxybenzene, 1,2,4- Tris-3-tris-perfluorooctanesulfonyloxybenzene, 1,2,4-tris-p-toluenesulfonyloxybenzene, 1,2,4-tris-perful It can be exemplified Rob Tan sulfonyloxy benzene.
式(XVIII)で示される酸発生剤としては、例えばコハク酸イミド・トリフルオロメタンスルホネート、コハク酸イミド・パーフルオロブタンスルホネート、コハク酸イミド・パーフルオロオクタンスルホネート、コハク酸イミド・p−トルエンスルホネート、コハク酸イミド・10−カンファースルホネート、コハク酸イミド・メタンスルホネート、コハク酸イミド・1−メチルエタンスルホネート、コハク酸イミド・ベンゼンスルホネート、ジメチルコハク酸イミド・トリフルオロメタンスルホネート、ジメチルコハク酸イミド・パーフルオロオクタンスルホネート、ジメチルコハク酸イミド・p−トルエンスルホネート、フタル酸イミド・トリフルオロメタンスルホネート、フタル酸イミド・パーフルオロブタンスルホネート、フタル酸イミド・パーフルオロオクタンスルホネート、フタル酸イミド・p−トルエンスルホネート、フタル酸イミド・10−カンファースルホネート、フタル酸イミド・メタンスルホネート、フタル酸イミド・ベンゼンスルホネート、5−ノルボルネン−2,3−ジカルボキシイミド・トリフルオロメタンスルホネート、5−ノルボルネン−2,3−ジカルボキシイミド・パーフルオロブタンスルホネート、5−ノルボルネン−2,3-ジカルボキシイミド・パーフルオロオクタンスルホネート、5−ノルボルネン−2,3−ジカルボキシイミド・ p-トルエンスルホネート、5−ノルボルネン−2,3−ジカルボキシイミド・10−カンファースルホネート、5−ノルボルネン−2,3−ジカルボキシイミド・メタンスルホネート等を例示することができる。 Examples of the acid generator represented by the formula (XVIII) include succinimide / trifluoromethanesulfonate, succinimide / perfluorobutanesulfonate, succinimide / perfluorooctanesulfonate, succinimide / p-toluenesulfonate, succinate. Acid imide, 10-camphor sulfonate, succinimide, methane sulfonate, succinimide, 1-methylethane sulfonate, succinimide, benzene sulfonate, dimethyl succinimide, trifluoromethane sulfonate, dimethyl succinimide, perfluorooctane sulfonate , Dimethyl succinimide / p-toluene sulfonate, phthalic imide / trifluoromethane sulfonate, phthalic imide / perfluorobutane sulfonate, phthalic acid Imido perfluorooctane sulfonate, phthalic imide p-toluene sulfonate, phthalic imide 10-camphor sulfonate, phthalic imide methane sulfonate, phthalic imide benzene sulfonate, 5-norbornene-2,3-dicarboximide Trifluoromethanesulfonate, 5-norbornene-2,3-dicarboximidePerfluorobutanesulfonate, 5-norbornene-2,3-dicarboximidePerfluorooctanesulfonate, 5-norbornene-2,3-dicarboximide Examples include p-toluenesulfonate, 5-norbornene-2,3-dicarboximide, 10-camphorsulfonate, 5-norbornene-2,3-dicarboximide, methanesulfonate, and the like.
レジスト用組成物として用いる場合、式(I)で表される繰返し単位を有する重合体を1種以上と、アルカリ可溶性重合体を混合し、式(XIV)〜(XVIII)で表される酸発生剤から選ばれる1種又は任意の2種以上を組み合わせて用いるのが好ましい。酸発生剤を2種以上組み合わせて使用する場合の好ましい例としては、光透過性が良好でレジスト組成物の高透明性が維持出来、露光後の加熱処理(PEB)温度依存性が少なく、かつ露光により弱酸を発生する式(XIV)で示される酸発生剤と、一定の露光量に対して酸発生効率が高い、又は強酸を発生する式(XV)、式(XVI)、式(XVII)又は式(XVIII)で示される酸発生剤とを組み合わせて使用することがパターンの裾部の形状改善及びスカム除去の点から好ましく、この中でも、式(XIV)で示される酸発生剤と、式(XV)又は/及び式(XVI)で示される酸発生剤とを組み合わせて使用するのが特に好ましい。 When used as a resist composition, one or more polymers having a repeating unit represented by formula (I) and an alkali-soluble polymer are mixed to generate an acid represented by formulas (XIV) to (XVIII). It is preferable to use 1 type selected from an agent or 2 or more types in combination. As a preferable example in the case of using two or more kinds of acid generators in combination, the light transmittance is good, the high transparency of the resist composition can be maintained, the heat treatment (PEB) temperature dependency after exposure is small, and An acid generator represented by the formula (XIV) that generates a weak acid by exposure, and a formula (XV), a formula (XVI), or a formula (XVII) that has a high acid generation efficiency or generates a strong acid for a certain exposure amount. Or it is preferable to use in combination with the acid generator represented by the formula (XVIII) from the viewpoint of improving the shape of the skirt of the pattern and removing the scum, and among them, the acid generator represented by the formula (XIV) and the formula It is particularly preferable to use in combination with an acid generator represented by (XV) or / and formula (XVI).
また、2種以上の酸発生剤を併用する場合の酸発生剤の構成比率としては、式(XIV)で示される酸発生剤100重量部に対して式(XV)、式(XVI)又は式(XVII)で示される酸発生剤は1〜70重量部、好ましくは10〜50重量部が挙げられる。 Moreover, as a constituent ratio of the acid generator when two or more acid generators are used in combination, the formula (XV), the formula (XVI), or the formula with respect to 100 parts by weight of the acid generator represented by the formula (XIV) The acid generator represented by (XVII) is 1 to 70 parts by weight, preferably 10 to 50 parts by weight.
また、従来から用いられている種々のトリフェニルスルホニウム塩及びジフェニルヨードニウム塩(これ等のオニウム塩の陰イオンとして、PF6 -、AsF6 -、BF4 -等が挙げられる。)及びトリス(トリクロロメチル)−s−トリアジン/トリエタノールアミン、トリス(トリクロロメチル)−s−トリアジン/アセトアミド等を単独もしくは2種以上混合して、または前記した式(XIV)〜(XVIII)で表される化合物と混合して用いることができる。 In addition, various triphenylsulfonium salts and diphenyliodonium salts conventionally used (anions of these onium salts include PF 6 − , AsF 6 − , BF 4 − and the like) and tris (trichloro). Methyl) -s-triazine / triethanolamine, tris (trichloromethyl) -s-triazine / acetamide and the like, or a compound represented by the above formulas (XIV) to (XVIII) It can be used by mixing.
酸発生剤の配合量は、全ベース樹脂100部(重量部、以下同じ)に対して0.2〜15部、特に0.5〜8部とすることが好ましく、0.2部に満たないと露光時の酸発生量が少なく、感度及び解像力が劣る場合があり、15部を超えるとレジストの透過率が低下し、解像力が劣る場合がある。 The blending amount of the acid generator is preferably 0.2 to 15 parts, more preferably 0.5 to 8 parts, and less than 0.2 parts with respect to 100 parts of the total base resin (parts by weight, the same applies hereinafter). The amount of acid generated during exposure is small, and the sensitivity and resolution may be inferior. If the amount exceeds 15 parts, the transmittance of the resist may be lowered and the resolution may be inferior.
本発明の組成物は、(A)〜(C)成分以外に必要に応じて以下の成分を含有することができる。
(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)。
The composition of this invention can contain the following components as needed other than (A)-(C) component.
(D) Organic solvent The organic solvent is not particularly limited as long as it is an organic solvent in which the components (A) to (C) can be dissolved. Specifically, cyclohexanone, methyl-2-n-amyl ketone, etc. Ketones, alcohols such as 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol mono Ethers such as ethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, lactic acid ester Examples include esters such as chill, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, tert-butyl acetate, tert-butyl propionate, propylene glycol mono-tert-butyl ether acetate These can be used alone or in admixture of two or more, but are not limited thereto. In the present invention, among these organic solvents, diethylene glycol dimethyl ether, 1-ethoxy-2-propanol, and ethyl lactate, which are most excellent in solubility of the acid generator in the resist component, as well as propylene glycol monomethyl ether acetate, which is a safety solvent, are used. And mixed solvents thereof are preferably used.
(E) Basic compound As the basic compound, a compound capable of suppressing the diffusion rate when the acid generated from the acid generator diffuses into the resist film is suitable. By mixing such a basic compound, , The acid diffusion rate in the resist film is suppressed, resolution is improved, sensitivity change after exposure is suppressed, substrate and environment dependency is reduced, exposure margin, pattern profile, etc. can be improved (JP-A-5-232706, JP-A-5-249683, JP-A-5-158239, JP-A-5-24962, JP-A-5-257282, JP-A-5-289322, JP-A-5-289340, etc.).
このような塩基性化合物としては、第一級、第二級、第三級の脂肪族アミン類、混成アミン類、芳香族アミン類、複素環アミン類、カルボキシ基を有する含窒素化合物、スルホニル基を有する含窒素化合物、ヒドロキシ基を有する含窒素化合物、ヒドロキシフェニル基を有する含窒素化合物、アルコール性含窒素化合物、アミド誘導体、イミド誘導体等が挙げられるが、特に脂肪族アミンが好適に用いられる。 Examples of such basic compounds include primary, secondary, and tertiary aliphatic amines, hybrid amines, aromatic amines, heterocyclic amines, nitrogen-containing compounds having a carboxy group, and sulfonyl groups. A nitrogen-containing compound having a hydroxy group, a nitrogen-containing compound having a hydroxy group, a nitrogen-containing compound having a hydroxyphenyl group, an alcoholic nitrogen-containing compound, an amide derivative, an imide derivative, and the like. Particularly, an aliphatic amine is preferably used.
具体的には、第一級の脂肪族アミン類として、アンモニア、メチルアミン、エチルアミン、n−プロピルアミン、イソプロピルアミン、n−ブチルアミン、イソブチルアミン、sec−ブチルアミン、tert−ブチルアミン、ペンチルアミン、tert−アミルアミン、シクロペンチルアミン、ヘキシルアミン、シクロヘキシルアミン、ヘプチルアミン、オクチルアミン、ノニルアミン、デシルアミン、ドデシルアミン、セチルアミン、メチレンジアミン、エチレンジアミン、テトラエチレンペンタミン等が例示され、第二級の脂肪族アミン類として、ジメチルアミン、ジエチルアミン、ジ−n−プロピルアミン、ジイソプロピルアミン、ジ−n−ブチルアミン、ジイソブチルアミン、ジ−sec−ブチルアミン、ジペンチルアミン、ジシクロペンチルアミン、ジヘキシルアミン、ジシクロヘキシルアミン、ジヘプチルアミン、ジオクチルアミン、ジノニルアミン、ジデシルアミン、ジドデシルアミン、ジセチルアミン、N,N−ジメチルメチレンジアミン、N,N−ジメチルエチレンジアミン、N,N−ジメチルテトラエチレンペンタミン等が例示され、第三級の脂肪族アミン類として、トリメチルアミン、トリエチルアミン、トリ−n−プロピルアミン、トリイソプロピルアミン、トリ−n−ブチルアミン、トリイソブチルアミン、トリ−sec−ブチルアミン、トリペンチルアミン、トリシクロペンチルアミン、トリヘキシルアミン、トリシクロヘキシルアミン、トリヘプチルアミン、トリオクチルアミン、トリノニルアミン、トリデシルアミン、トリドデシルアミン、トリセチルアミン、N,N,N’,N’−テトラメチルメチレンジアミン、N,N,N’,N’−テトラメチルエチレンジアミン、N,N,N’,N’−テトラメチルテトラエチレンペンタミン等が例示される。 Specifically, primary aliphatic amines include ammonia, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine, pentylamine, tert- Amylamine, cyclopentylamine, hexylamine, cyclohexylamine, heptylamine, octylamine, nonylamine, decylamine, dodecylamine, cetylamine, methylenediamine, ethylenediamine, tetraethylenepentamine, etc. are exemplified as secondary aliphatic amines. Dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, diisobutylamine, di-sec-butylamine, dipentylamine, disi Lopentylamine, dihexylamine, dicyclohexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, didodecylamine, dicetylamine, N, N-dimethylmethylenediamine, N, N-dimethylethylenediamine, N, N-dimethyltetraethylenepenta Examples of tertiary aliphatic amines include trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, and tripentylamine. , Tricyclopentylamine, trihexylamine, tricyclohexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, tridodecylamine, Examples include cetylamine, N, N, N ′, N′-tetramethylmethylenediamine, N, N, N ′, N′-tetramethylethylenediamine, N, N, N ′, N′-tetramethyltetraethylenepentamine and the like. Is done.
また、混成アミン類としては、例えばジメチルエチルアミン、メチルエチルプロピルアミン、ベンジルアミン、フェネチルアミン、ベンジルジメチルアミン等が例示される。芳香族アミン類及び複素環アミン類の具体例としては、アニリン誘導体(例えばアニリン、N−メチルアニリン、N−エチルアニリン、N−プロピルアニリン、N,N−ジメチルアニリン、2−メチルアニリン、3−メチルアニリン、4−メチルアニリン、エチルアニリン、プロピルアニリン、トリメチルアニリン、2−ニトロアニリン、3−ニトロアニリン、4−ニトロアニリン、2,4−ジニトロアニリン、2,6−ジニトロアニリン、3,5−ジニトロアニリン、N,N−ジメチルトルイジン等)、ジフェニル(p−トリル)アミン、メチルジフェニルアミン、トリフェニルアミン、フェニレンジアミン、ナフチルアミン、ジアミノナフタレン、ピロール誘導体(例えばピロール、2H−ピロール、1−メチルピロール、2,4−ジメチルピロール、2,5−ジメチルピロール、N−メチルピロール等)、オキサゾール誘導体(例えばオキサゾール、イソオキサゾール等)、チアゾール誘導体(例えばチアゾール、イソチアゾール等)、イミダゾール誘導体(例えばイミダゾール、4−メチルイミダゾール、4−メチル−2−フェニルイミダゾール等)、ピラゾール誘導体、フラザン誘導体、ピロリン誘導体(例えばピロリン、2−メチル−1−ピロリン等)、ピロリジン誘導体(例えばピロリジン、N−メチルピロリジン、ピロリジノン、N−メチルピロリドン等)、イミダゾリン誘導体、イミダゾリジン誘導体、ピリジン誘導体(例えばピリジン、メチルピリジン、エチルピリジン、プロピルピリジン、ブチルピリジン、4−(1−ブチルペンチル)ピリジン、ジメチルピリジン、トリメチルピリジン、トリエチルピリジン、フェニルピリジン、3−メチル−2−フェニルピリジン、4−tert−ブチルピリジン、ジフェニルピリジン、ベンジルピリジン、メトキシピリジン、ブトキシピリジン、ジメトキシピリジン、1−メチル−2−ピリドン、4−ピロリジノピリジン、1−メチル−4−フェニルピリジン、2−(1−エチルプロピル)ピリジン、アミノピリジン、ジメチルアミノピリジン等)、ピリダジン誘導体、ピリミジン誘導体、ピラジン誘導体、ピラゾリン誘導体、ピラゾリジン誘導体、ピペリジン誘導体、ピペラジン誘導体、モルホリン誘導体、インドール誘導体、イソインドール誘導体、1H−インダゾール誘導体、インドリン誘導体、キノリン誘導体(例えばキノリン、3−キノリンカルボニトリル等)、イソキノリン誘導体、シンノリン誘導体、キナゾリン誘導体、キノキサリン誘導体、フタラジン誘導体、プリン誘導体、プテリジン誘導体、カルバゾール誘導体、フェナントリジン誘導体、アクリジン誘導体、フェナジン誘導体、1,10−フェナントロリン誘導体、アデニン誘導体、アデノシン誘導体、グアニン誘導体、グアノシン誘導体、ウラシル誘導体、ウリジン誘導体等が例示される。 Examples of hybrid amines include dimethylethylamine, methylethylpropylamine, benzylamine, phenethylamine, and benzyldimethylamine. Specific examples of aromatic amines and heterocyclic amines include aniline derivatives (eg, aniline, N-methylaniline, N-ethylaniline, N-propylaniline, N, N-dimethylaniline, 2-methylaniline, 3- Methylaniline, 4-methylaniline, ethylaniline, propylaniline, trimethylaniline, 2-nitroaniline, 3-nitroaniline, 4-nitroaniline, 2,4-dinitroaniline, 2,6-dinitroaniline, 3,5- Dinitroaniline, N, N-dimethyltoluidine, etc.), diphenyl (p-tolyl) amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, pyrrole derivatives (eg pyrrole, 2H-pyrrole, 1-methylpyrrole, 2,4-dim Lupyrrole, 2,5-dimethylpyrrole, N-methylpyrrole, etc.), oxazole derivatives (eg oxazole, isoxazole etc.), thiazole derivatives (eg thiazole, isothiazole etc.), imidazole derivatives (eg imidazole, 4-methylimidazole, 4 -Methyl-2-phenylimidazole, etc.), pyrazole derivatives, furazane derivatives, pyrroline derivatives (eg pyrroline, 2-methyl-1-pyrroline etc.), pyrrolidine derivatives (eg pyrrolidine, N-methylpyrrolidine, pyrrolidinone, N-methylpyrrolidone etc.) ), Imidazoline derivatives, imidazolidine derivatives, pyridine derivatives (eg pyridine, methylpyridine, ethylpyridine, propylpyridine, butylpyridine, 4- (1-butylpentyl) pyridine, dimethyl) Lysine, trimethylpyridine, triethylpyridine, phenylpyridine, 3-methyl-2-phenylpyridine, 4-tert-butylpyridine, diphenylpyridine, benzylpyridine, methoxypyridine, butoxypyridine, dimethoxypyridine, 1-methyl-2-pyridone, 4-pyrrolidinopyridine, 1-methyl-4-phenylpyridine, 2- (1-ethylpropyl) pyridine, aminopyridine, dimethylaminopyridine, etc.), pyridazine derivatives, pyrimidine derivatives, pyrazine derivatives, pyrazoline derivatives, pyrazolidine derivatives, piperidine Derivatives, piperazine derivatives, morpholine derivatives, indole derivatives, isoindole derivatives, 1H-indazole derivatives, indoline derivatives, quinoline derivatives (eg quinoline, 3-quinoline carbo Nitriles), isoquinoline derivatives, cinnoline derivatives, quinazoline derivatives, quinoxaline derivatives, phthalazine derivatives, purine derivatives, pteridine derivatives, carbazole derivatives, phenanthridine derivatives, acridine derivatives, phenazine derivatives, 1,10-phenanthroline derivatives, adenine derivatives, adenosine Examples include derivatives, guanine derivatives, guanosine derivatives, uracil derivatives, uridine derivatives and the like.
更に、カルボキシ基を有する含窒素化合物としては、例えばアミノ安息香酸、インドールカルボン酸、アミノ酸誘導体(例えばニコチン酸、アラニン、アルギニン、アスパラギン酸、グルタミン酸、グリシン、ヒスチジン、イソロイシン、グリシルロイシン、ロイシン、メチオニン、フェニルアラニン、スレオニン、リジン、3−アミノピラジン−2−カルボン酸、メトキシアラニン)等が例示され、スルホニル基を有する含窒素化合物として3−ピリジンスルホン酸、p−トルエンスルホン酸ピリジニウム等が例示され、ヒドロキシ基を有する含窒素化合物、ヒドロキシフェニル基を有する含窒素化合物、アルコール性含窒素化合物としては、2−ヒドロキシピリジン、アミノクレゾール、2,4−キノリンジオール、3−インドールメタノールヒドレート、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、N−エチルジエタノールアミン、N,N−ジエチルエタノールアミン、トリイソプロパノールアミン、2,2’−イミノジエタノール、2−アミノエタノ−ル、3−アミノ−1−プロパノール、4−アミノ−1−ブタノール、4−(2−ヒドロキシエチル)モルホリン、2−(2−ヒドロキシエチル)ピリジン、1−(2−ヒドロキシエチル)ピペラジン、1−[2−(2−ヒドロキシエトキシ)エチル]ピペラジン、ピペリジンエタノール、1−(2−ヒドロキシエチル)ピロリジン、1−(2−ヒドロキシエチル)−2−ピロリジノン、3−ピペリジノ−1,2−プロパンジオール、3−ピロリジノ−1,2−プロパンジオール、8−ヒドロキシユロリジン、3−クイヌクリジノール、3−トロパノール、1−メチル−2−ピロリジンエタノール、1−アジリジンエタノール、N−(2−ヒドロキシエチル)フタルイミド、N−(2−ヒドロキシエチル)イソニコチンアミド等が例示される。アミド誘導体としては、ホルムアミド、N−メチルホルムアミド、N,N−ジメチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、プロピオンアミド、ベンズアミド等が例示される。イミド誘導体としては、フタルイミド、サクシンイミド、マレイミド、トリス{2−(メトキシメトキシ)エチル}アミン、トリス{2−(メトキシエトキシ)エチル}アミン、トリス[2−{(2−メトキシエトキシ)メトキシ}エチル]アミン、トリス{2−(2−メトキシエトキシ)エチル}アミン、トリス{2−(1−メトキシエトキシ)エチル}アミン、トリス{2−(1−エトキシエトキシ)エチル}アミン、トリス{2−(1−エトキシプロポキシ)エチル}アミン、トリス[2−{(2−ヒドロキシエトキシ)エトキシ}エチル]アミン、4,7,13,16,21,24−ヘキサオキサ−1,10−ジアザビシクロ[8.8.8]ヘキサコサン、4,7,13,18−テトラオキサ−1,10−ジアザビシクロ[8.5.5]エイコサン、1,4,10,13−テトラオキサ−7,16−ジアザビシクロオクタデカン、1−アザ−12−クラウン−4、1−アザ−15−クラウン−5、1−アザ−18−クラウン−6等を例示することができる。 Furthermore, examples of the nitrogen-containing compound having a carboxy group include aminobenzoic acid, indolecarboxylic acid, amino acid derivatives (for example, nicotinic acid, alanine, arginine, aspartic acid, glutamic acid, glycine, histidine, isoleucine, glycylleucine, leucine, methionine. , Phenylalanine, threonine, lysine, 3-aminopyrazine-2-carboxylic acid, methoxyalanine) and the like, and examples of the nitrogen-containing compound having a sulfonyl group include 3-pyridinesulfonic acid, pyridinium p-toluenesulfonate, and the like. Nitrogen-containing compounds having a hydroxy group, nitrogen-containing compounds having a hydroxyphenyl group, and alcoholic nitrogen-containing compounds include 2-hydroxypyridine, aminocresol, 2,4-quinolinediol, 3-indolemeta Hydrate, monoethanolamine, diethanolamine, triethanolamine, N-ethyldiethanolamine, N, N-diethylethanolamine, triisopropanolamine, 2,2'-iminodiethanol, 2-aminoethanol, 3-amino-1-propanol 4-amino-1-butanol, 4- (2-hydroxyethyl) morpholine, 2- (2-hydroxyethyl) pyridine, 1- (2-hydroxyethyl) piperazine, 1- [2- (2-hydroxyethoxy) Ethyl] piperazine, piperidineethanol, 1- (2-hydroxyethyl) pyrrolidine, 1- (2-hydroxyethyl) -2-pyrrolidinone, 3-piperidino-1,2-propanediol, 3-pyrrolidino-1,2-propane Diol, 8-hydroxy Loridine, 3-cuincridinol, 3-tropanol, 1-methyl-2-pyrrolidine ethanol, 1-aziridine ethanol, N- (2-hydroxyethyl) phthalimide, N- (2-hydroxyethyl) isonicotinamide, etc. Illustrated. Examples of amide derivatives include formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, propionamide, benzamide and the like. Examples of the imide derivative include phthalimide, succinimide, maleimide, tris {2- (methoxymethoxy) ethyl} amine, tris {2- (methoxyethoxy) ethyl} amine, tris [2-{(2-methoxyethoxy) methoxy} ethyl]. Amine, tris {2- (2-methoxyethoxy) ethyl} amine, tris {2- (1-methoxyethoxy) ethyl} amine, tris {2- (1-ethoxyethoxy) ethyl} amine, tris {2- (1 -Ethoxypropoxy) ethyl} amine, tris [2-{(2-hydroxyethoxy) ethoxy} ethyl] amine, 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo [8.8.8] ] Hexacosane, 4,7,13,18-tetraoxa-1,10-diazabicyclo [8.5. ] Eicosane, 1,4,10,13-tetraoxa-7,16-diazabicyclooctadecane, 1-aza-12-crown-4, 1-aza-15-crown-5, 1-aza-18-crown- 6 etc. can be illustrated.
特に第三級アミン、アニリン誘導体、ピロリジン誘導体、ピリジン誘導体、キノリン誘導体、アミノ酸誘導体、ヒドロキシ基を有する含窒素化合物、ヒドロキシフェニル基を有する含窒素化合物、アルコール性含窒素化合物、アミド誘導体、イミド誘導体、トリス{2−(メトキシメトキシ)エチル}アミン、トリス{(2−(2−メトキシエトキシ)エチル}アミン、トリス[2−{(2−メトキシエトキシ)メチル}エチル]アミン、1−アザ−15−クラウン−5等が好ましい。 Especially tertiary amines, aniline derivatives, pyrrolidine derivatives, pyridine derivatives, quinoline derivatives, amino acid derivatives, nitrogen-containing compounds having a hydroxy group, nitrogen-containing compounds having a hydroxyphenyl group, alcoholic nitrogen-containing compounds, amide derivatives, imide derivatives, Tris {2- (methoxymethoxy) ethyl} amine, tris {(2- (2-methoxyethoxy) ethyl} amine, tris [2-{(2-methoxyethoxy) methyl} ethyl] amine, 1-aza-15- Crown-5 and the like are preferable.
なお、上記塩基性化合物は1種を単独で又は2種以上を組み合わせて用いることができ、その配合量は全ベース樹脂100部に対して2部以下、好ましくは0.01〜2部、特に0.01〜1部が好適である。配合量が0.01部より少ないと配合効果がなく、2部を超えると感度が低下しすぎる場合がある。
(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。
In addition, the said basic compound can be used individually by 1 type or in combination of 2 or more types, The compounding quantity is 2 parts or less with respect to 100 parts of all base resins, Preferably it is 0.01-2 parts, Especially. 0.01-1 part is preferred. If the blending amount is less than 0.01 part, there is no blending effect, and if it exceeds 2 parts, the sensitivity may be too low.
(F) Aromatic carboxylic acid An aromatic compound having a group represented by ≡C—COOH in the molecule can be added to the resist composition of the present invention. By blending the component (F), the PED stability of the resist can be improved, and the edge roughness on the nitride film substrate can be improved. Specific examples of such a compound include compounds represented by the following formulae.
なお、上記分子内に≡C−COOHで示される基を有する芳香族化合物は、1種を単独で又は2種以上を組み合わせて用いることができる。 The aromatic compound having a group represented by ≡C—COOH in the molecule can be used alone or in combination of two or more.
上記分子内に≡C−COOHで示される基を有する芳香族化合物の添加量は、ベース樹脂100部に対して5部以下、好ましくは0.1〜5部、より好ましくは1〜3部である。0.1部より少ないと窒化膜基板上での裾引き及びPEDの改善効果が十分に得られない場合があり、5部より多いとレジスト材料の解像性が低下する場合がある。
(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。
The amount of the aromatic compound having a group represented by ≡C—COOH in the molecule is 5 parts or less, preferably 0.1 to 5 parts, more preferably 1 to 3 parts relative to 100 parts of the base resin. is there. If the amount is less than 0.1 part, the tailing on the nitride film substrate and the effect of improving PED may not be sufficiently obtained. If the amount is more than 5 parts, the resolution of the resist material may be lowered.
(G) Dissolution Control Agent A dissolution control agent can be added to the resist material of the present invention for adjusting the dissolution rate, thereby improving the contrast. As a dissolution controller, an average molecular weight of 100 to 1,000, preferably 150 to 800, and a compound having two or more phenolic hydroxyl groups in the molecule, the entire hydrogen atom of the phenolic hydroxyl group is converted to an acid labile group. As an average, 0 to 100 mol% of the substituted compound is blended.
なお、フェノール性水酸基の水素原子の酸不安定基による置換率は、平均でフェノール性水酸基全体の0モル%以上、好ましくは30モル%以上であり、また、その上限は100モル%、より好ましくは80モル%である。 The substitution rate of the hydrogen atom of the phenolic hydroxyl group by an acid labile group is on average 0 mol% or more, preferably 30 mol% or more of the entire phenolic hydroxyl group, and the upper limit is more preferably 100 mol%. Is 80 mol%.
この場合、かかるフェノール性水酸基を2つ以上有する化合物としては、下記に示す化合物を例示することができる。 In this case, examples of the compound having two or more phenolic hydroxyl groups include the compounds shown below.
ここで、溶解制御剤の酸不安定基としては、炭素数4〜20の三級アルキル基、各アルキル基がそれぞれ炭素数1〜6のトリアルキルシリル基、炭素数4〜20のオキソアルキル基等が挙げられる。 Here, as the acid labile group of the dissolution controller, a tertiary alkyl group having 4 to 20 carbon atoms, a trialkylsilyl group having 1 to 6 carbon atoms, and an oxoalkyl group having 4 to 20 carbon atoms, respectively. Etc.
上記フェノール性水酸基を酸不安定基で部分置換した化合物(溶解制御剤)の配合量は、ベース樹脂100部に対し、0〜50部、好ましくは5〜50部、より好ましくは10〜30部であり、単独又は2種以上を混合して使用できる。配合量が5部に満たないと解像性の向上がない場合があり、50部を超えるとパターンの膜減りが生じ、解像度が低下する場合がある。 The compounding amount of the compound in which the phenolic hydroxyl group is partially substituted with an acid labile group (dissolution control agent) is 0 to 50 parts, preferably 5 to 50 parts, more preferably 10 to 30 parts relative to 100 parts of the base resin. It can be used alone or in admixture of two or more. If the blending amount is less than 5 parts, the resolution may not be improved, and if it exceeds 50 parts, the film thickness of the pattern may be reduced and the resolution may be lowered.
なお、上記のような溶解制御剤は、フェノール性水酸基を有する化合物にベース樹脂と同様に酸不安定基を化学反応させることにより合成することができる。
(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。
The dissolution control agent as described above can be synthesized by chemically reacting an acid labile group with a compound having a phenolic hydroxyl group in the same manner as the base resin.
(H) Ultraviolet Absorber Further, the resist material of the present invention may contain a compound having a molar absorbance at a wavelength of 248 nm of 10,000 or less as an ultraviolet absorber. This makes it possible to design and control a resist having an appropriate transmittance for substrates having different reflectivities.
具体的には、ペンタレン、インデン、ナフタレン、アズレン、ペプタレン、ビフェニレン、インダセン、フルオレン、フェナレン、フェナントレン、アントラセン、フルオランテン、アセフェナントリレン、アセアントリレン、トリフェニレン、ピレン、クリセン、ナフタレン、プレイアデン、ピセン、ペリレン、ペンタフェン、ペンタセン、ベンゾフェナントレン、アントラキノン、アントロンベンズアントロン、2,7−ジメトキシナフタレン、2−エチル−9,10−ジメトキシアントセラン、9,10−ジメチルアントラセン、9−エトキシアントラセン、1,2−ナフトキノン、9−フルオレン等の縮合多環炭化水素誘導体、チオキサンテン−9−オン、チアントレン、ジベンゾチオフェン等の縮合複素環誘導体、2,3,4−トリビトロキシベンゾフェノン、2,3,4,4’−テトラヒドロキシベンゾフェノン、2,4−ジヒドロキシベンゾフェノン、3,5−ジヒドロキシベンゾフェノン、4,4’−ジヒドロキシベンゾフェノン、4,4’−ビス(ジメチルアミノ)ベンゾフェノン等のベンゾフェノン誘導体、スクエアル酸、ジメチルスクエアレート等のスクエアル酸誘導体等が挙げられる。 Specifically, pentalene, indene, naphthalene, azulene, peptalene, biphenylene, indacene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, pyrene, chrysene, naphthalene, preaden, picene Perylene, pentaphene, pentacene, benzophenanthrene, anthraquinone, anthrone benzanthrone, 2,7-dimethoxynaphthalene, 2-ethyl-9,10-dimethoxyanthcerane, 9,10-dimethylanthracene, 9-ethoxyanthracene, 1,2 -Condensed polycyclic hydrocarbon derivatives such as naphthoquinone and 9-fluorene, condensed heterocyclic derivatives such as thioxanthen-9-one, thianthrene and dibenzothiophene, 2,3,4-to Vitroxybenzophenone, 2,3,4,4′-tetrahydroxybenzophenone, 2,4-dihydroxybenzophenone, 3,5-dihydroxybenzophenone, 4,4′-dihydroxybenzophenone, 4,4′-bis (dimethylamino) benzophenone And benzophenone derivatives such as squaric acid derivatives such as squaric acid and dimethyl squarate.
また、紫外線吸収剤としては、ビス(4−ヒドロキシフェニル)スルホキシド、ビス(4−tert−ブトキシフェニル)スルホキシド、ビス(4−tert−ブトキシカルボニルオキシフェニル)スルホキシド、ビス[4−(1−エトキシエトキシ)フェニル]スルホキシド等のジアリールスルホキシド誘導体、ビス(4−ヒドロキシフェニル)スルホン、ビス(4−tert−ブトキシフェニル)スルホン、ビス(4−tert−ブトキシカルボニルオキシフェニル)スルホン、ビス[4−(1−エトキシエトキシ)フェニル]スルホン、ビス[4−(1−エトキシプロポキシ)フェニル]スルホン等のジアリールスルホン誘導体、ベンゾキノンジアジド、ナフトキノンジアジド、アントラキノンジアジド、ジアゾフルオレン、ジアゾテトラロン、ジアゾフェナントロン等のジアゾ化合物、ナフトキノン−1,2−ジアジド−5−スルホン酸クロリドと2,3,4−トリヒドロキシベンゾフェノンとの完全もしくは部分エステル化合物、ナフトキノン−1,2−ジアジド−4−スルホン酸クロリドと2,4,4’−トリヒドロキシベンゾフェノンとの完全もしくは部分エステル化合物等のキノンジアジド基含有化合物等を用いることもできる。 Examples of the ultraviolet absorber include bis (4-hydroxyphenyl) sulfoxide, bis (4-tert-butoxyphenyl) sulfoxide, bis (4-tert-butoxycarbonyloxyphenyl) sulfoxide, and bis [4- (1-ethoxyethoxy). ) Phenyl] sulfoxide derivatives such as diaryl sulfoxide derivatives, bis (4-hydroxyphenyl) sulfone, bis (4-tert-butoxyphenyl) sulfone, bis (4-tert-butoxycarbonyloxyphenyl) sulfone, bis [4- (1- Diarylsulfone derivatives such as ethoxyethoxy) phenyl] sulfone, bis [4- (1-ethoxypropoxy) phenyl] sulfone, benzoquinonediazide, naphthoquinonediazide, anthraquinonediazide, diazofluorene, diazote Diazo compounds such as laron and diazophenantrone, naphthoquinone-1,2-diazide-5-sulfonic acid chloride and 2,3,4-trihydroxybenzophenone complete or partial ester compound, naphthoquinone-1,2-diazide- A quinonediazide group-containing compound such as a complete or partial ester compound of 4-sulfonic acid chloride and 2,4,4′-trihydroxybenzophenone can also be used.
紫外線吸収剤として好ましくは、9−アントラセンカルボン酸tert−ブチル、9−アントラセンカルボン酸tert−アミル、9−アントラセンカルボン酸tert−メトキシメチル、9−アントラセンカルボン酸tert−エトキシエチル、9−アントラセンカルボン酸tert−テトラヒドロピラニル、9−アントラセンカルボン酸tert−テトラヒドロフラニル、ナフトキノン−1,2−ジアジド−5−スルホン酸クロリドと2,3,4−トリヒドロキシベンゾフェノンとの部分エステル化合物等を挙げることができる。 As the UV absorber, tert-butyl 9-anthracenecarboxylate, tert-amyl 9-anthracenecarboxylate, tert-methoxymethyl 9-anthracenecarboxylate, tert-ethoxyethyl 9-anthracenecarboxylate, 9-anthracenecarboxylic acid tert-tetrahydropyranyl, 9-anthracenecarboxylic acid tert-tetrahydrofuranyl, naphthoquinone-1,2-diazide-5-sulfonic acid chloride and partial ester compound of 2,3,4-trihydroxybenzophenone .
上記紫外線吸収剤の配合量は、ベース樹脂100部に対して0〜10部、より好ましくは0.5〜10部、更に好ましくは1〜5部であることが好ましい。 The blending amount of the ultraviolet absorber is preferably 0 to 10 parts, more preferably 0.5 to 10 parts, and still more preferably 1 to 5 parts with respect to 100 parts of the base resin.
その他の添加剤 更に、本発明のレジスト組成物にはアセチレンアルコール誘導体を配合することができ、これにより保存安定性を向上させることができる。具体的には、 サーフィノール61、サーフィノール82、サーフィノール104、サーフィノール104E、サーフィノール104H、サーフィノール104A、サーフィノールTG、サーフィノールPC、サーフィノール440、サーフィノール465、サーフィノール485(Air Products and Chemicals Inc.製)、サーフィノールE1004(日信化学工業(株)製)等を例示することができる。 Other additives Furthermore, an acetylene alcohol derivative can be mix | blended with the resist composition of this invention, and, thereby, storage stability can be improved. Specifically, Surfinol 61, Surfinol 82, Surfinol 104, Surfinol 104E, Surfinol 104H, Surfinol 104A, Surfinol TG, Surfinol PC, Surfinol 440, Surfinol 465, Surfinol 485 (Air) Products and Chemicals Inc.), Surfynol E1004 (Nisshin Chemical Industry Co., Ltd.) and the like can be exemplified.
上記アセチレンアルコール誘導体の添加量は、レジスト組成物100重量%中2重量%以下、好ましくは0.01〜2重量%、より好ましくは0.02〜1重量%である。0.01重量%より少ないと塗布性及び保存安定性の改善効果が十分に得られない場合があり、2重量%より多いとレジスト材料の解像性が低下する場合がある。 The amount of the acetylene alcohol derivative added is 2% by weight or less, preferably 0.01 to 2% by weight, more preferably 0.02 to 1% by weight in 100% by weight of the resist composition. When the amount is less than 0.01% by weight, the effect of improving the coating property and storage stability may not be sufficiently obtained. When the amount is more than 2% by weight, the resolution of the resist material may be lowered.
界面活性剤 本発明のレジスト材料には、上記成分以外に任意成分として塗布性を向上させるために慣用されている界面活性剤を添加することができる。なお、任意成分の添加量は、本発明の効果を妨げない範囲で通常量とすることができる。 Surfactant To the resist material of the present invention, a surfactant conventionally used for improving coatability can be added as an optional component in addition to the above components. In addition, the addition amount of an arbitrary component can be made into a normal amount in the range which does not inhibit the effect of this invention.
ここで、界面活性剤としては非イオン性のものが好ましく、パーフルオロアルキルポリオキシエチレンエタノール、フッ素化アルキルエステル、パーフルオロアルキルアミンオキサイド、含フッ素オルガノシロキサン系化合物等が挙げられる。例えばフロラード「FC−430」、「FC−431」(いずれも住友スリーエム(株)製)、サーフロン「S−381」、「S−383」(いずれも旭硝子(株)製)、ユニダイン「DS−401」、「DS−403」、「DS−451」(いずれもダイキン工業(株)製)、メガファック「F−171」「F−172」「F−173」「F−177」(大日本インキ工業(株)製)、「X−70−092」、「X−70−093」(いずれも信越化学工業(株)製)等を挙げることができる。好ましくは、フロラード「FC−430」(住友スリーエム(株)製)、「X−70−093」(信越化学工業(株)製)が挙げられる。 Here, the surfactant is preferably nonionic, and examples thereof include perfluoroalkyl polyoxyethylene ethanol, fluorinated alkyl ester, perfluoroalkylamine oxide, and fluorinated organosiloxane compound. For example, Florard “FC-430”, “FC-431” (all manufactured by Sumitomo 3M Limited), Surflon “S-381”, “S-383” (all manufactured by Asahi Glass Co., Ltd.), Unidyne “DS- 401 ”,“ DS-403 ”,“ DS-451 ”(all manufactured by Daikin Industries, Ltd.), MegaFuck“ F-171 ”“ F-172 ”“ F-173 ”“ F-177 ”(Dainippon) Ink Industry Co., Ltd.), “X-70-092”, “X-70-093” (all manufactured by Shin-Etsu Chemical Co., Ltd.), and the like. Preferably, Florard “FC-430” (manufactured by Sumitomo 3M Co., Ltd.), “X-70-093” (manufactured by Shin-Etsu Chemical Co., Ltd.) can be used.
本発明のレジスト組成物を使用してパターンを形成するには、公知のリソグラフィー技術を採用して行うことができ、例えばシリコンウェハー等の基板上にスピンコーティング等の手法で膜厚が0.5〜2.0μmとなるように塗布し、これをホットプレート上で60〜150℃、1〜10分間、好ましくは80〜120℃、1〜5分間プリベークする。次いで目的のパターンを形成するためのマスクを上記のレジスト膜上にかざし、波長300nm以下の遠紫外線、エキシマレーザー、X線等の高エネルギー線もしくは電子線を露光量1〜200mJ/cm2程度、好ましくは10〜100mJ/cm2程度となるように照射した後、ホットプレート上で60〜150℃、1〜5分間、好ましくは80〜120℃、1〜3分間ポストエクスポージャベーク(PEB)する。更に、0.1〜5%、好ましくは2〜3%テトラメチルアンモニウムハイドロオキサイド(TMAH)等のアルカリ水溶液の現像液を用い、0.1〜3分間、好ましくは0.5〜2分間、浸漬(dip)法、パドル(puddle)法、スプレー(spray)法等の常法により現像することにより基板上に目的のパターンが形成される。なお、本発明材料は、特に高エネルギー線の中でも254〜193nmの遠紫外線又はエキシマレーザー、X線及び電子線による微細パターンニングに最適である。また、上記範囲を上限及び下限から外れる場合は、目的のパターンを得ることができない場合がある。 In order to form a pattern using the resist composition of the present invention, a known lithography technique can be employed. For example, a film thickness of 0.5 can be formed on a substrate such as a silicon wafer by spin coating or the like. It is applied to a thickness of ˜2.0 μm and prebaked on a hot plate at 60 to 150 ° C. for 1 to 10 minutes, preferably 80 to 120 ° C. for 1 to 5 minutes. Next, a mask for forming a target pattern is placed over the resist film, and a high-energy ray such as far ultraviolet ray having a wavelength of 300 nm or less, an excimer laser, an X-ray, or an electron beam is applied in an exposure amount of about 1 to 200 mJ / cm2, preferably Is irradiated at a temperature of about 10 to 100 mJ / cm 2 and then post-exposure baking (PEB) on a hot plate at 60 to 150 ° C. for 1 to 5 minutes, preferably 80 to 120 ° C. for 1 to 3 minutes. Further, 0.1-5%, preferably 2-3% tetramethylammonium hydroxide (TMAH) or other alkaline aqueous developer is used for 0.1-3 minutes, preferably 0.5-2 minutes. A target pattern is formed on the substrate by developing by a conventional method such as a (dip) method, a paddle method, or a spray method. The material of the present invention is particularly suitable for fine patterning using deep ultraviolet rays of 254 to 193 nm or excimer laser, X-rays and electron beams among high energy rays. In addition, when the above range deviates from the upper limit and the lower limit, the target pattern may not be obtained.
以下、実施例を用いて、本発明をさらに詳細に説明するが、本発明は実施例に限定されるものではない。
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。
EXAMPLES Hereinafter, although this invention is demonstrated further in detail using an Example, this invention is not limited to an Example.
Reference example 1
(1) Synthesis of ethylphenylketene (EPK) In a nitrogen atmosphere, a THF solution of 55 g (0.3 mol) of 2-phenylbutyryl chloride was added dropwise to a THF mixed solution of 91 g (0.9 mol) of triethylamine. One hour later, the precipitated triethylamine hydrochloride was filtered, and the filtrate was distilled under reduced pressure to obtain EPK (60 to 70 ° C./4 mmHg). Yield 30 g (70% yield).
(2) 4- (t-Butoxycarbonyloxy) benzaldehyde (BOCBA)
In a nitrogen atmosphere, 24.4 g (0.2 mol) of 4-hydroxybenzaldehyde was dissolved in 200 ml of THF, 52.4 g (0.24 mol) of di-t-butyl dicarbonate, and 15 mg of N, N-dimethylaminopyridine. (0.2 mmol) was added and stirred at room temperature overnight. After neutralization by adding an aqueous Na 2 CO 3 solution, the solution was separated, and the upper layer was washed with water until pH = 7. MgSO 4 was added, dehydrated and filtered, concentrated and recrystallized from methanol to obtain BOCBA. Yield 35 g (80% yield).
(3) Alternating copolymerization of EPK and BOCBA Lithium chloride (1.9 g, 45 mmol) was heated and vacuum dried, and then added with 100 ml of THF in a nitrogen atmosphere and cooled to -40 ° C. Further, 4.4 g (32 mmol) of BOCBA and 4.4 g (30 mmol) of EPK were added, and then 0.93 ml (1.5 mmol) of n-BuLi in hexane was added, and the reaction was continued at −40 ° C. for 30 minutes. After stopping the reaction by adding methanol, the mixture was added to a large amount of methanol for reprecipitation, and the resulting precipitate was filtered and dried under reduced pressure to obtain 8.5 g of white powdery polymer (a). When the polymer (a) was analyzed by gel permeation chromatography (hereinafter abbreviated as “GPC”), it was a monodisperse polymer with Mn = 8000 and Mw / Mn = 1.18.
Reference example 2
After dissolving 50 g of poly (p-hydroxystyrene) [Nippon Soda Co., Ltd. VP-15000, Mn = 18000, Mw / Mn = 1.10] in 200 ml of ethyl acetate under nitrogen atmosphere, 15 g of ethyl vinyl ether and 0. 3 ml was added and stirred at room temperature for one day. Next, water was added to the reaction solution for separation, and washing was repeated until neutrality. After concentration, the polymer was precipitated by pouring it into a large amount of methanol, filtered, washed and then vacuum dried to obtain polymer (b). When GPC analysis of the polymer (b) was carried out, it was Mn = 21000, Mw / Mn = 1.10, and the acetal group protection rate measured by NMR was 42%.
ポリマー(b)70重量部にポリマー(a)30重量部を混合して樹脂固形分濃度12%になるようにプロピレングリコルモノメチルエーテルアセテート(PGMEA)に溶解し、さらに、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を樹脂固形分に対して1.0重量%になるように添加し、レジスト溶液を調整した。スピンコーターで上記レジスト溶液を用いてシリコンウエハー上に成膜し、ホットプレート上で90℃60秒間加熱し、膜厚400nmの薄膜を得た。超高圧水銀灯(365nmで照度10mW)の光で露光後、ホットプレート110℃、90秒間加熱した後、2.38%テトラメチルアンモニウムヒドロオキシド水溶液を用いて溶解速度を測定した。露光量と溶解速度の関係をまとめて図1に示す。
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。
30 parts by weight of polymer (a) is mixed with 70 parts by weight of polymer (b) and dissolved in propylene glycol monomethyl ether acetate (PGMEA) so as to have a resin solid content concentration of 12%. Further, triphenylsulfonium trifluoromethanesulfonate Was added so that it might become 1.0 weight% with respect to resin solid content, and the resist solution was adjusted. A film was formed on a silicon wafer using the resist solution by a spin coater and heated on a hot plate at 90 ° C. for 60 seconds to obtain a thin film having a thickness of 400 nm. After exposure with light from an ultra high pressure mercury lamp (illuminance of 10 mW at 365 nm), the plate was heated at 110 ° C. for 90 seconds, and then the dissolution rate was measured using a 2.38% tetramethylammonium hydroxide aqueous solution. The relationship between exposure dose and dissolution rate is summarized in FIG.
Comparative Example 1
Except that the polymer (b) was used alone, the dissolution rate was measured in the same manner as in the Examples, and the relationship between the exposure amount and the dissolution rate is summarized in FIG.
図1より、本発明の組成物は、式(I)で表される繰り返し単位を有する重合体を含まない比較例1に比して、低露光量において溶解を制御できることがわかった。高露光量においては溶解速度が急激に上昇することから、本発明の組成物を用いることで、コントラストの優れたパターンを形成できることがわかった。 From FIG. 1, it was found that the composition of the present invention can control dissolution at a low exposure amount as compared with Comparative Example 1 that does not include a polymer having a repeating unit represented by formula (I). Since the dissolution rate rapidly increased at a high exposure amount, it was found that a pattern having excellent contrast can be formed by using the composition of the present invention.
Claims (6)
(A) A polymer that becomes alkali-soluble upon reaction with an acid is represented by the formula (III)
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2006206648A (en) * | 2005-01-25 | 2006-08-10 | Nippon Soda Co Ltd | Resin composition |
JP2006206650A (en) * | 2005-01-25 | 2006-08-10 | Nippon Soda Co Ltd | Heat-decomposable resin containing ketene and aldehyde copolymer |
WO2014034541A1 (en) * | 2012-08-30 | 2014-03-06 | セントラル硝子株式会社 | Photosensitive resin composition and pattern formation method using same |
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JP2006206651A (en) * | 2005-01-25 | 2006-08-10 | Nippon Soda Co Ltd | Decomposable resin composition comprising ketene-aldehyde copolymer |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006206648A (en) * | 2005-01-25 | 2006-08-10 | Nippon Soda Co Ltd | Resin composition |
JP2006206650A (en) * | 2005-01-25 | 2006-08-10 | Nippon Soda Co Ltd | Heat-decomposable resin containing ketene and aldehyde copolymer |
WO2014034541A1 (en) * | 2012-08-30 | 2014-03-06 | セントラル硝子株式会社 | Photosensitive resin composition and pattern formation method using same |
JP2014063148A (en) * | 2012-08-30 | 2014-04-10 | Central Glass Co Ltd | Photosensitive resin composition and pattern formation method using the same |
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