JP4371206B2 - エステル化合物、高分子化合物、レジスト材料、及びパターン形成方法 - Google Patents
エステル化合物、高分子化合物、レジスト材料、及びパターン形成方法 Download PDFInfo
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- JP4371206B2 JP4371206B2 JP2003330904A JP2003330904A JP4371206B2 JP 4371206 B2 JP4371206 B2 JP 4371206B2 JP 2003330904 A JP2003330904 A JP 2003330904A JP 2003330904 A JP2003330904 A JP 2003330904A JP 4371206 B2 JP4371206 B2 JP 4371206B2
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- -1 Ester compound Chemical class 0.000 title claims description 410
- 150000001875 compounds Chemical class 0.000 title claims description 64
- 239000000463 material Substances 0.000 title claims description 41
- 229920000642 polymer Polymers 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 157
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 74
- 150000002430 hydrocarbons Chemical group 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 33
- 125000004122 cyclic group Chemical group 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 17
- 150000003949 imides Chemical class 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 17
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 16
- 150000002170 ethers Chemical class 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 15
- 150000001299 aldehydes Chemical class 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 238000010894 electron beam technology Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 3
- JLVDVIXDYDGVLS-UHFFFAOYSA-N 3-oxabicyclo[2.2.1]heptane Chemical compound C1C2CCC1OC2 JLVDVIXDYDGVLS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 239000000178 monomer Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 239000007983 Tris buffer Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 125000002524 organometallic group Chemical group 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 150000007514 bases Chemical class 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 125000005188 oxoalkyl group Chemical group 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 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 6
- 239000003960 organic solvent Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 5
- VINRTVDNUHIWCB-UHFFFAOYSA-N 2,2,2-trifluoro-1-(2,4,6-trimethylphenyl)ethanone Chemical compound CC1=CC(C)=C(C(=O)C(F)(F)F)C(C)=C1 VINRTVDNUHIWCB-UHFFFAOYSA-N 0.000 description 5
- NCJZVRPXSSYDBG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1 NCJZVRPXSSYDBG-UHFFFAOYSA-N 0.000 description 5
- DYILUJUELMWXAL-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C=C1 DYILUJUELMWXAL-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- 0 CCNC(OC(P*)=O)(P)ICC Chemical compound CCNC(OC(P*)=O)(P)ICC 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 5
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 238000005935 nucleophilic addition reaction Methods 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
- 150000003839 salts Chemical class 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KYXIHKXHBSORRJ-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-2,2,2-trifluoroethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C(C)=C1 KYXIHKXHBSORRJ-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
- KJXSTIJHXKFZKV-UHFFFAOYSA-N 2-(cyclohexylmethylsulfanyl)cyclohexan-1-one;trifluoromethanesulfonic acid Chemical compound [O-]S(=O)(=O)C(F)(F)F.O=C1CCCCC1[SH+]CC1CCCCC1 KJXSTIJHXKFZKV-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
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- 238000006467 substitution reaction Methods 0.000 description 3
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 description 2
- VLLPVDKADBYKLM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;triphenylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VLLPVDKADBYKLM-UHFFFAOYSA-M 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- YFISYXOGMSGFRE-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-2,2,2-trifluoroethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1OC YFISYXOGMSGFRE-UHFFFAOYSA-N 0.000 description 2
- SCKJMHAZRHWHTP-UHFFFAOYSA-N 1-(4-benzylphenyl)-2,2,2-trifluoroethanone Chemical compound C1=CC(C(=O)C(F)(F)F)=CC=C1CC1=CC=CC=C1 SCKJMHAZRHWHTP-UHFFFAOYSA-N 0.000 description 2
- OXOLZTWHBOKBRB-UHFFFAOYSA-N 1-(7-oxabicyclo[2.2.1]heptan-3-yl)cyclopentan-1-ol Chemical compound C1C(O2)CCC2C1C1(O)CCCC1 OXOLZTWHBOKBRB-UHFFFAOYSA-N 0.000 description 2
- YRFBNNUJAYITGP-UHFFFAOYSA-N 1-(oxolan-2-yl)cyclopentan-1-ol Chemical compound C1CCOC1C1(O)CCCC1 YRFBNNUJAYITGP-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
- WNQSKPOIYILBMI-UHFFFAOYSA-N 1-[butylsulfonyl(diazo)methyl]sulfonylbutane Chemical compound CCCCS(=O)(=O)C(=[N+]=[N-])S(=O)(=O)CCCC WNQSKPOIYILBMI-UHFFFAOYSA-N 0.000 description 2
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 2
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- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- UPWIJTYOHJOEOX-UHFFFAOYSA-M trifluoromethanesulfonate;trinaphthalen-1-ylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2C([S+](C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 UPWIJTYOHJOEOX-UHFFFAOYSA-M 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000000233 ultraviolet lithography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0395—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having a backbone with alicyclic moieties
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
Description
(I)下記一般式(1)で示されるエステル化合物。
(II)下記一般式(2)で示されるエステル化合物。
(III)下記一般式(3)で示されるエステル化合物。
(IV)下記一般式(1a)で示される繰り返し単位を含有することを特徴とする高分子化合物。
(V)下記一般式(1b)及び(1c)で示されるいずれかの繰り返し単位を含有することを特徴とする高分子化合物。
(VI)更に、下記一般式(M1)〜(M13)で示されるいずれかの繰り返し単位を含有する(IV)又は(V)記載の高分子化合物。
(VII)上記(IV)、(V)又は(VI)に記載の高分子化合物をベース樹脂として含有することを特徴とするレジスト材料。
(VIII)上記(VII)に記載のレジスト材料を基板上に塗布する工程と、加熱処理後フォトマスクを介して高エネルギー線もしくは電子線で露光する工程と、必要に応じて加熱処理した後、現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
i)第一の方法としては、有機金属試薬(4)のケトン化合物(5)への求核付加反応により中間体アルコール化合物(11)を合成できる。
有機金属試薬(4)の使用量は、ケトン化合物(5)1モルに対して、0.5〜2.0モル、特に0.9〜1.2モルとすることが望ましい。溶媒としてテトラヒドロフラン、ジエチルエーテル、ジ−n−ブチルエーテル、1,4−ジオキサン等のエーテル類、n−ヘキサン、n−ヘプタン、ベンゼン、トルエン、キシレン、クメン等の炭化水素類が好ましく、これらの溶媒を単独もしくは混合して使用することができる。反応温度、反応時間は、条件により種々異なるが、例えば、有機金属試薬としてGrignard試薬{式(4)において、MがMgPの場合}を用いる場合は、反応温度を−20〜80℃、好ましくは0〜50℃で行う。反応時間はガスクロマトグラフィー(GC)やシリカゲル薄層クロマトグラフィー(TLC)で反応を追跡して反応を完結させることが収率の点で望ましいが、通常0.5〜10時間程度である。反応混合物から通常の水系後処理(aqueous work−up)により中間体アルコール化合物(11)を得ることができ、必要があれば蒸留、クロマトグラフィー等の常法に従って精製することができる。
有機金属試薬(6)の使用量は、ケトン化合物(7)1モルに対して、1.0〜3.0モル、特に1.1〜1.5モルとすることが望ましい。溶媒としてテトラヒドロフラン、ジエチルエーテル、ジ−n−ブチルエーテル、1,4−ジオキサン等のエーテル類、n−ヘキサン、n−ヘプタン、ベンゼン、トルエン、キシレン、クメン等の炭化水素類が好ましく、これらの溶媒を単独もしくは混合して使用することができる。反応温度、反応時間は、条件により種々異なるが、例えば、有機金属試薬としてGrignard試薬{式(6)において、MがMgPの場合}を用いる場合は、反応温度を−20〜80℃、好ましくは0〜50℃で行う。反応時間はガスクロマトグラフィー(GC)やシリカゲル薄層クロマトグラフィー(TLC)で反応を追跡して反応を完結させることが収率の点で望ましいが、通常0.5〜10時間程度である。反応混合物から通常の水系後処理(aqueous work−up)により中間体アルコール化合物(11)を得ることができ、必要があれば蒸留、クロマトグラフィー等の常法に従って精製することができる。
有機金属試薬(6)及び(8)の使用量は、カルボニル化合物(9)1モルに対して、2.0〜5.0モル、特に2.0〜3.0モルとすることが望ましい。溶媒としてテトラヒドロフラン、ジエチルエーテル、ジ−n−ブチルエーテル、1,4−ジオキサン等のエーテル類、n−ヘキサン、n−ヘプタン、ベンゼン、トルエン、キシレン、クメン等の炭化水素類が好ましく、これらの溶媒を単独もしくは混合して使用することができる。反応温度、反応時間は、条件により種々異なるが、例えば、有機金属試薬としてGrignard試薬{式(6)及び(8)において、MがMgPの場合}を用いる場合は、反応温度を0〜100℃、好ましくは20〜70℃で行う。反応時間はガスクロマトグラフィー(GC)やシリカゲル薄層クロマトグラフィー(TLC)で反応を追跡して反応を完結させることが収率の点で望ましいが、通常0.5〜10時間程度である。反応混合物から通常の水系後処理(aqueous work−up)により中間体アルコール化合物(11)を得ることができ、必要があれば蒸留、クロマトグラフィー等の常法に従って精製することができる。
一般式(1)で示されるエステル化合物から得られる繰り返し単位として、具体的には下記式(1a)〜(1c)を挙げることができる。
(式中、A 2 、R 3 、及びk 1 は上記と同様である。R 1 、R 2 は互いに結合してこれらが結合する炭素原子と共に脂肪族炭化水素環を形成する。)
上記式(L4)の酸不安定基としては、具体的には下記の基が例示できる。
(I)上記式(1)の単量体に基づく式(1a)〜(1c)で示される構成単位の1種又は2種以上を0モル%を超え100モル%、好ましくは10〜80モル%、より好ましくは20〜60モル%含有し、
(II)上記式(M1)〜(M13)で示される構成単位の1種又は2種以上を0モル%以上、100モル%未満、好ましくは1〜95モル%、より好ましくは40〜80モル%含有し、必要に応じ、
(III)その他の単量体に基づく構成単位の1種又は2種以上を0〜80モル%、好ましくは0〜70モル%、より好ましくは0〜50モル%含有することができる。
本発明の高分子化合物を製造する共重合反応は種々例示することができるが、好ましくはラジカル重合、アニオン重合又は配位重合である。
i.下記一般式(P1a−1)、(P1a−2)又は(P1b)のオニウム塩、
ii.下記一般式(P2)のジアゾメタン誘導体、
iii.下記一般式(P3)のグリオキシム誘導体、
iv.下記一般式(P4)のビススルホン誘導体、
v.下記一般式(P5)のN−ヒドロキシイミド化合物のスルホン酸エステル、
vi.β−ケトスルホン酸誘導体、
vii.ジスルホン誘導体、
viii.ニトロベンジルスルホネート誘導体、
ix.スルホン酸エステル誘導体
x.オキシムスルホン酸エステル
等が挙げられる。
p−トルエンスルホン酸2,6−ジニトロベンジル、p−トルエンスルホン酸2,4−ジニトロベンジル等のニトロベンジルスルホネート誘導体。
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(p−トルエンスルホニルオキシ)ベンゼン等のスルホン酸エステル誘導体。
なお、上記のような溶解阻止剤は、フェノール性水酸基又はカルボキシ基を有する化合物に対し、有機化学的処方を用いて酸不安定基を導入することにより合成される。
塩基性化合物としては、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いる。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。
N(X)n(Y)3-n (B)−1
式中、n=1、2又は3である。側鎖Xは同一でも異なっていてもよく、下記一般式(X)−1〜(X)−3で表すことができる。側鎖Yは同一又は異種の、水素原子もしくは直鎖状、分岐状又は環状の炭素数1〜20のアルキル基を示し、エーテル基もしくはヒドロキシル基を含んでもよい。また、X同士が結合して環を形成してもよい。
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−(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、トリス(2−フォルミルオキシエチル)アミン、トリス(2−ホルミルオキシエチル)アミン、トリス(2−アセトキシエチル)アミン、トリス(2−プロピオニルオキシエチル)アミン、トリス(2−ブチリルオキシエチル)アミン、トリス(2−イソブチリルオキシエチル)アミン、トリス(2−バレリルオキシエチル)アミン、トリス(2−ピバロイルオキシエチル)アミン、N,N−ビス(2−アセトキシエチル)2−(アセトキシアセトキシ)エチルアミン、トリス(2−メトキシカルボニルオキシエチル)アミン、トリス(2−tert−ブトキシカルボニルオキシエチル)アミン、トリス[2−(2−オキソプロポキシ)エチル]アミン、トリス[2−(メトキシカルボニルメチル)オキシエチル]アミン、トリス[2−(tert−ブトキシカルボニルメチルオキシ)エチル]アミン、トリス[2−(シクロヘキシルオキシカルボニルメチルオキシ)エチル]アミン、トリス(2−メトキシカルボニルエチル)アミン、トリス(2−エトキシカルボニルエチル)アミン、N,N−ビス(2−ヒドロキシエチル)2−(メトキシカルボニル)エチルアミン、N,N−ビス(2−アセトキシエチル)2−(メトキシカルボニル)エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−(エトキシカルボニル)エチルアミン、N,N−ビス(2−アセトキシエチル)2−(エトキシカルボニル)エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−(2−メトキシエトキシカルボニル)エチルアミン、N,N−ビス(2−アセトキシエチル)2−(2−メトキシエトキシカルボニル)エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−(2−ヒドロキシエトキシカルボニル)エチルアミン、N,N−ビス(2−アセトキシエチル)2−(2−アセトキシエトキシカルボニル)エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−[(メトキシカルボニル)メトキシカルボニル]エチルアミン、N,N−ビス(2−アセトキシエチル)2−[(メトキシカルボニル)メトキシカルボニル]エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−(2−オキソプロポキシカルボニル)エチルアミン、N,N−ビス(2−アセトキシエチル)2−(2−オキソプロポキシカルボニル)エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−(テトラヒドロフルフリルオキシカルボニル)エチルアミン、N,N−ビス(2−アセトキシエチル)2−(テトラヒドロフルフリルオキシカルボニル)エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−[(2−オキソテトラヒドロフラン−3−イル)オキシカルボニル]エチルアミン、N,N−ビス(2−アセトキシエチル)2−[(2−オキソテトラヒドロフラン−3−イル)オキシカルボニル]エチルアミン、N,N−ビス(2−ヒドロキシエチル)2−(4−ヒドロキシブトキシカルボニル)エチルアミン、N,N−ビス(2−ホルミルオキシエチル)2−(4−ホルミルオキシブトキシカルボニル)エチルアミン、N,N−ビス(2−ホルミルオキシエチル)2−(2−ホルミルオキシエトキシカルボニル)エチルアミン、N,N−ビス(2−メトキシエチル)2−(メトキシカルボニル)エチルアミン、N−(2−ヒドロキシエチル)ビス[2−(メトキシカルボニル)エチル]アミン、N−(2−アセトキシエチル)ビス[2−(メトキシカルボニル)エチル]アミン、N−(2−ヒドロキシエチル)ビス[2−(エトキシカルボニル)エチル]アミン、N−(2−アセトキシエチル)ビス[2−(エトキシカルボニル)エチル]アミン、N−(3−ヒドロキシ−1−プロピル)ビス[2−(メトキシカルボニル)エチル]アミン、N−(3−アセトキシ−1−プロピル)ビス[2−(メトキシカルボニル)エチル]アミン、N−(2−メトキシエチル)ビス[2−(メトキシカルボニル)エチル]アミン、N−ブチルビス[2−(メトキシカルボニル)エチル]アミン、N−ブチルビス[2−(2−メトキシエトキシカルボニル)エチル]アミン、N−メチルビス(2−アセトキシエチル)アミン、N−エチルビス(2−アセトキシエチル)アミン、N−メチルビス(2−ピバロイルオキシエチル)アミン、N−エチルビス[2−(メトキシカルボニルオキシ)エチル]アミン、N−エチルビス[2−(tert−ブトキシカルボニルオキシ)エチル]アミン、トリス(メトキシカルボニルメチル)アミン、トリス(エトキシカルボニルメチル)アミン、N−ブチルビス(メトキシカルボニルメチル)アミン、N−ヘキシルビス(メトキシカルボニルメチル)アミン、β−(ジエチルアミノ)−δ−バレロラクトンを例示できるが、これらに制限されない。
分子内に≡C−COOHで示される基を有する化合物としては、例えば下記[I群]及び[II群]から選ばれる1種又は2種以上の化合物を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。本成分の配合により、レジストのPED安定性が向上し、窒化膜基板上でのエッジラフネスが改善されるのである。
[I群]
下記一般式(A1)〜(A10)で示される化合物のフェノール性水酸基の水素原子の一部又は全部を−R401−COOH(R401は炭素数1〜10の直鎖状又は分岐状のアルキレン基)により置換してなり、かつ分子中のフェノール性水酸基(C)と≡C−COOHで示される基(D)とのモル比率がC/(C+D)=0.1〜1.0である化合物。
[II群]
下記一般式(A11)〜(A15)で示される化合物。
アセチレンアルコール誘導体としては、下記一般式(S1)、(S2)で示されるものを好適に使用することができる。
本発明のエステル化合物を以下に示す処方で合成した。
[合成例1−1]monomer1の合成
マグネシウム13.6gとテトラヒドロフラン300mlをフラスコに収め、1,4−ジブロモブタン60.3gを50℃にて滴下した。滴下終了後、60℃にて1時間撹拌した後、40℃以下にて、テトラヒドロフランカルボン酸エチル31.0gを滴下した。室温で1時間撹拌した後、塩化アンモニウム水溶液を加え、加水分解した。通常の後処理操作を行い、30.2gの1−(2−テトラヒドロフラニル)シクロペンタノールが得られた。
1−(2−テトラヒドロフラニル)シクロペンタノール16.8g、トリエチルアミン13.1g、4−(N,N−ジメチルアミノ)ピリジン0.5gをトルエン80mlに溶解した。50℃にてアクリル酸クロリド10.7gを加え、そのままの温度で1時間撹拌した。水50mlを30℃以下で加え、通常の後処理操作を行った。減圧蒸留を行い、アクリル酸1−(2−テトラヒドロフラニル)シクロペンチル18.1gを得た(二工程収率80%)。
沸点:84−86℃/86Pa
IR(薄膜):ν=2954,2871,1720,1635,1619,1450,1402,1298,1207,1170,1074,1049,983,811cm-1
1H−NMR(300MHz in CDCl3):δ=1.49−2.25(12H,m),3.70−3.92(2H,m),4.57(1H,t),5.72(1H,dd),6.04(1H,dd),6.29(1H,dd)ppm
1Mメチルマグネシウムクロリドのテトラヒドロフラン溶液240mlをフラスコに収め、40℃以下にて、7−オキサ−2−ノルボルナンカルボン酸メチル15.6gを滴下した。室温で1時間撹拌した後、塩化アンモニウム水溶液を加え、加水分解した。通常の後処理操作を行い、14.8gの2−(7−オキサノルボルナン−2−イル)−2−プロパノールが得られた。
2−(7−オキサノルボルナン−2−イル)−2−プロパノール12.5g、トリエチルアミン12.1g、4−(N,N−ジメチルアミノ)ピリジン0.4gをトルエン80mlに溶解した。50℃にてアクリル酸クロリド9.1gを加え、そのままの温度で1時間撹拌した。水50mlを30℃以下で加え、通常の後処理操作を行った。減圧蒸留を行い、アクリル酸2−(7−オキサノルボルナン−2−イル)−2−プロピル13.8gを得た(二工程収率82%)。
沸点:86−88℃/40Pa
IR(薄膜):ν=2978,2950,2873,1720,1635,1467,1452,1402,1367,1299,1232,1207,1166,1136,1045,998,930,887,847,811,777cm-1
主要異性体の1H−NMR(300MHz in CDCl3):δ=1.41−1.93{1.53(3H,s)及び1.61(3H,s)を含む11H,m},2.07−2.18(2H,m),4.47(1H,t),4.58(1H,t),5.75(1H,dd),6.03(1H,dd),6.31(1H,dd)ppm
アクリル酸クロリドの替わりにメタクリル酸クロリドを使用した以外は合成例1−2と同様な方法でメタクリル酸2−(7−オキサノルボルナン−2−イル)−2−プロピルを得た(二工程収率76%)。
沸点:87−88/27Pa
IR(薄膜):ν=2977,2952,2910,2873,1712,1637,1469,1452,1400,1384,1367,1326,1305,1240,1207,1180,1159,1133,1029,1000,973,931,887,848,815,783,777cm-1
主要異性体の1H−NMR(300MHz in CDCl3):δ=1.46−1.68{1.52(3H,s)及び1.62(3H,s)を含む9H,m},1.69−1.82(1H,m),1.83−1.93(4H,m),2.08−2.18(2H,m),4.48(1H,t),4.58(1H,t),5.50(1H,m),5.99(1H,m)ppm
マグネシウム14.6gとテトラヒドロフラン270mlをフラスコに収め、1,4−ジブロモブタン64.8gを50℃にて滴下した。滴下終了後、60℃にて1時間撹拌した後、40℃以下にて、7−オキサ−2−ノルボルナンカルボン酸メチル39.0gを滴下した。室温で1時間撹拌した後、塩化アンモニウム水溶液を加え、加水分解した。通常の後処理操作を行い、43.7gの1−(7−オキサノルボルナン−2−イル)シクロペンタノールが得られた。
1−(7−オキサノルボルナン−2−イル)シクロペンタノール18.2g、トリエチルアミン15.2g、4−(N,N−ジメチルアミノ)ピリジン0.5gをトルエン80mlに溶解した。50℃にてアクリル酸クロリド12.5gを加え、そのままの温度で1時間撹拌した。水50mlを30℃以下で加え、通常の後処理操作を行った。減圧蒸留を行い、アクリル酸1−(7−オキサノルボルナン−2−イル)シクロペンチル19.7gを得た(二工程収率84%)。
沸点:95−98/29Pa
IR(薄膜):ν=2960,2873,1720,1633,1619,1469,1450,1402,1332,1297,1280,1197,1168,1120,1045,998,985,962,944,881,811cm-1
主要異性体の1H−NMR(600MHz in CDCl3):δ=1.31(1H,dd),1.41−1.48(1H,m),1.52−1.93(9H,m),1.99−2.05(1H,m),2.22−2.26(1H,m),2.35−2.43(1H,m),2.75−2.81(1H,m),4.39(1H,t),4.57(1H,t),5.75(1H,dd),6.04(1H,dd),6.31(1H,dd)ppm
アクリル酸クロリドの替わりにメタクリル酸クロリドを使用した以外は合成例1−4と同様な方法でメタクリル酸1−(7−オキサノルボルナン−2−イル)シクロペンチルを得た(二工程収率73%)。
沸点:94−96/13Pa
IR(薄膜):ν=2975,2956,2873,1712,1637,1469,1450,1400,1376,1328,1303,1270,1180,1159,1002,987,939,883,848,815cm-1
主要異性体の1H−NMR(300MHz in CDCl3):δ=1.30(1H,dd),1.41−1.50(1H,m),1.52−2.07(13H,m),2.16−2.18(1H,m),2.35−2.47(1H,m),2.78−2.89(1H,m),4.38(1H,t),4.57(1H,t),5.49(1H,m),5.99(1H,m)ppm
29.5gのmonomer1をトルエン30mlに溶解し、30℃以下でシクロペンタジエン11.6gを滴下した。50℃にて10時間撹拌し、減圧蒸留により、5−ノルボルネン−2−カルボン酸1−(2−テトラヒドロフラニル)シクロペンチル37.1gを得た(収率96%)。
沸点:116−118/33Pa
IR(薄膜):ν=2971,2871,1727,1448,1336,1270,1232,1203,1167,1108,1072,1024,995,937,865,839,711cm-1
主要異性体の1H−NMR(300MHz in CDCl3):δ=1.20−2.25(17H,m),2.81−2.94(2H,m),3.16(1H,s),3.68−3.89(2H,m),4.47(1H,t),5.86−5.97(1H,m),6.14−6.22(1H,m)ppm
monomer1の替わりにmonomer2を使用した以外は合成例1−6と同様な方法で5−ノルボルネン−2−カルボン酸2−(7−オキサノルボルナン−2−イル)−2−プロピルを得た(収率95%)。
沸点:120−122/13Pa
IR(薄膜):ν=3060,2973,2946,2871,1727,1463,1450,1382,1365,1336,1301,1272,1253,1230,1205,1187,1164,1133,1108,1027,998,973,931,917,887,838,815,709cm-1
主要異性体の1H−NMR(600MHz in CDCl3):δ=1.27(1H,t),1.35−1.67(11H,m),1.72−1.91(3H,m),2.05−2.24(2H,m),2.88−2.91(2H,m),3.18(1H,s),4.46(1H,t),4.57−4.61(1H,m),5.88−5.95(1H,m),6.18−6.21(1H,m)ppm
monomer1の替わりにmonomer4を使用した以外は合成例1−6と同様な方法で5−ノルボルネン−2−カルボン酸1−(7−オキサノルボルナン−2−イル)シクロペンチルを得た(収率93%)。
沸点:132−135/13Pa
IR(薄膜):ν=3060,2973,2871,1725,1471,1448,1334,1270,1230,1191,1164,1132,1108,1022,1000,941,883,838,815,709cm-1
主要異性体の1H−NMR(600MHz in CDCl3) :δ=1.24−1.33(4H,m),1.47−1.69(6H,m),1.74−1.92(5H,m),2.01−2.19(2H,m),2.23−2.33(1H,m),2.66−2.71(1H,m),2.87−2.91(2H,m),3.17(1H,s),4.36−4.40(1H,m),4.54−4.59(1H,m),5.90−5.95(1H,m),6.17−6.21(1H,m)ppm
本発明の高分子化合物を以下に示す処方で合成した。
[合成例2−1]Polymer1の合成
78.5gのmonomer1、70.9gのメタクリル酸ヒドロキシアダマンチル、77.8gのメタクリル酸4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン−2−イル及び1500gのテトラヒドロフランを混合した。この反応混合物を60℃まで加熱し、6.4gの2,2’−アゾビス(2,4−ジメチルバレロニトリル)を加え、60℃を保ちながら15時間撹拌した。室温まで冷却した後、反応液を、9Lのメタノールに激しく撹拌しながら滴下した。生じた固形物を濾過して取り、40℃で15時間真空乾燥したところ、下記式Polymer1で示される白色粉末固体状の高分子化合物が得られた。収量は209g、収率は92%であった。なお、Mwは、ポリスチレン換算でのGPCを用いて測定した重量平均分子量を表す。
上記と同様にして、又は公知の処方で、Polymer2〜7を合成した。
本発明の高分子化合物について、ベース樹脂としてレジスト材料に配合した際の疎密依存性及び解像性の評価を行った。
[実施例1−1〜7及び比較例1−1,2]
上記式で示されるポリマー(Polymer1〜7)及び比較として下記式で示されるポリマー(Polymer8,9)をベース樹脂とし、酸発生剤、塩基性化合物、及び溶剤を、表1に示す組成で混合した。次にそれらをテフロン(登録商標)製フィルター(孔径0.2μm)で濾過し、レジスト材料とした。
TPSNf:ノナフルオロブタンスルホン酸トリフェニルスルホニウム
TMMEA:トリスメトキシメトキシエチルアミン
PGMEA:プロピレングリコールモノメチルエーテルアセテート
Claims (8)
- 更に、下記一般式(M1)〜(M13)で示されるいずれかの繰り返し単位を含有する請求項4又は5記載の高分子化合物。
- 請求項4、5又は6に記載の高分子化合物をベース樹脂として含有することを特徴とするレジスト材料。
- 請求項7に記載のレジスト材料を基板上に塗布する工程と、加熱処理後フォトマスクを介して高エネルギー線もしくは電子線で露光する工程と、必要に応じて加熱処理した後、現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
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US7232638B2 (en) * | 2002-05-02 | 2007-06-19 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
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- 2003-09-26 EP EP03256075.7A patent/EP1403295B1/en not_active Expired - Lifetime
- 2003-09-29 TW TW092126885A patent/TWI301832B/zh not_active IP Right Cessation
- 2003-09-29 US US10/671,948 patent/US7132215B2/en not_active Expired - Lifetime
- 2003-09-29 KR KR1020030067258A patent/KR100809819B1/ko active IP Right Grant
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US7132215B2 (en) | 2006-11-07 |
EP1403295B1 (en) | 2014-10-22 |
EP1403295A3 (en) | 2004-04-14 |
JP2004143153A (ja) | 2004-05-20 |
EP1403295A2 (en) | 2004-03-31 |
KR20040028553A (ko) | 2004-04-03 |
KR100809819B1 (ko) | 2008-03-04 |
US20060234160A1 (en) | 2006-10-19 |
TWI301832B (en) | 2008-10-11 |
US20040068124A1 (en) | 2004-04-08 |
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