CN1727997A - Novel sulfonium salt compound capable of being used as photosensitive acid generator and preparation method thereof - Google Patents
Novel sulfonium salt compound capable of being used as photosensitive acid generator and preparation method thereof Download PDFInfo
- Publication number
- CN1727997A CN1727997A CN 200510038661 CN200510038661A CN1727997A CN 1727997 A CN1727997 A CN 1727997A CN 200510038661 CN200510038661 CN 200510038661 CN 200510038661 A CN200510038661 A CN 200510038661A CN 1727997 A CN1727997 A CN 1727997A
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- CN
- China
- Prior art keywords
- alkyl
- oxo
- general formula
- compound
- methyl
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title abstract description 30
- -1 sulfonium salt compound Chemical class 0.000 title description 120
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 239000003795 chemical substances by application Substances 0.000 claims description 43
- 241001597008 Nomeidae Species 0.000 claims description 7
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 3
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 3
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 abstract description 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000003367 polycyclic group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000001259 photo etching Methods 0.000 description 22
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 19
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 206010034972 Photosensitivity reaction Diseases 0.000 description 11
- 238000004132 cross linking Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 230000036211 photosensitivity Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 238000001459 lithography Methods 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 230000003321 amplification Effects 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 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 5
- 150000002500 ions Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003199 nucleic acid amplification method Methods 0.000 description 5
- AZLIIAMTCHKNJJ-UHFFFAOYSA-N potassium;trifluoromethanesulfonic acid Chemical compound [K].OS(=O)(=O)C(F)(F)F AZLIIAMTCHKNJJ-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 4
- 125000004337 3-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 125000006431 methyl cyclopropyl group Chemical group 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
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- BQDDAGUCZIAAQI-UHFFFAOYSA-N trifluoromethanesulfonic acid;hydrochloride Chemical compound Cl.OS(=O)(=O)C(F)(F)F BQDDAGUCZIAAQI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 2
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 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 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 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 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- VDCOTRGOYNBXRU-UHFFFAOYSA-N 2,3-difluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(F)=C1F VDCOTRGOYNBXRU-UHFFFAOYSA-N 0.000 description 1
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
- RJFMDYQCCOOZHJ-UHFFFAOYSA-L 2-hydroxyethyl(trimethyl)azanium dihydroxide Chemical compound [OH-].[OH-].C[N+](C)(C)CCO.C[N+](C)(C)CCO RJFMDYQCCOOZHJ-UHFFFAOYSA-L 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- HUWROFPLFCTNEQ-UHFFFAOYSA-N 3-bromo-2-methylbut-1-ene Chemical group CC(Br)C(C)=C HUWROFPLFCTNEQ-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- UPXJFTFKYLSTDL-UHFFFAOYSA-N [K].C(CCC)S(=O)(=O)O.[F] Chemical compound [K].C(CCC)S(=O)(=O)O.[F] UPXJFTFKYLSTDL-UHFFFAOYSA-N 0.000 description 1
- KVXNKFYSHAUJIA-UHFFFAOYSA-N acetic acid;ethoxyethane Chemical class CC(O)=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940053198 antiepileptics succinimide derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940000489 arsenate Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MYMDYWSMEBELMC-UHFFFAOYSA-M hydroxymethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CO MYMDYWSMEBELMC-UHFFFAOYSA-M 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical class COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- RPMOERPGTQLCAT-UHFFFAOYSA-M triethyl(hydroxymethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CO RPMOERPGTQLCAT-UHFFFAOYSA-M 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention relates to a compound of a general formula I and a preparation method thereof. Wherein: r1，R2Independently is C1－12An alkyl group or a cyclic structure formed by an alkylene structure, and the alkyl group or the cycloalkyl group may or may not contain an oxygen complex structure; z1Is a substituent structure of a general formula II; z2，Z3Independently of hydrogen, C1－6Alkyl radical, C1－6Alkoxy radical, C3－7Cycloalkyl, halogen, C1－6Haloalkyl or equal to Z1(ii) a Wherein Z2，Z3Not simultaneously equal to hydrogen. R3，R4，R5Independently hydrogen, alkyl of linear, branched, monocyclic, polycyclic, crosslinked cyclic character, C1－10An unsaturated alkenyl or alkynyl group; y-represents a counter anion. The compound with the structure shown in the general formula I is suitable for being used as a photosensitive acid generator in a photoresist composition.
Description
Technical field: the present invention relates to new sulfosalt compound that has the alkenylene chain feature and preparation method thereof.It is used as photosensitive acid agent in photoetching compositions.Target compound of the present invention is particularly useful for the photosensitive acid agent of photoetching under the extreme ultraviolet wavelength, typically can be ArF excimer laser (wavelength: 193nm) in the photoetching occasion as exposure light source.
Background technology: in the VLSI (very large scale integrated circuit) semiconductor production, the chemical amplifying type photoresist is used in research in using as the photoresist process of KrF, ArF, VUV and EUV light source recently, obtains high sensitivity during with the fine image of formation on semiconductor devices.This photo-corrosion-resisting agent composition generally by with photosensitive acid agent with have a matrix resin polymer manufacture of acid-unstable group.In photoetching process, the resolution of image depends on used optical wavelength.Therefore, wavelength is short more, and resolution is high more, and promptly shorter wavelength can form more tiny image.Corresponding to≤0.15 μ m photoetching technique, be applicable to ArF excimer laser (wavelength: 193nm) and F
2(wavelength: 157nm) photoresist of exposure light source has developed into mainstream technology to excimer laser.Generality about 193nm wavelength ArF photoetching technique is described in Photopolymer Science andTechnology 5 (3) (1992), 8 (4) (1995), sets forth in 9 (3) (1996).Consider ArF and F
2In the excimer laser lasing time of gas very short, its desired corresponding photoresist need have good sensitivity.248nm and more will depend on the chemical amplification reaction principle during short wavelength's resist exposure.Adopt photosensitive acid agent (PAG) as the chemical amplification photoresist of photosensitizer by general use, its in use, the photon of absorption decomposes photosensitive acid agent (PAG), generates acid catalyst.
JP2-27660 has announced typical chemical amplification photoetching compositions, and its constituent is triphenyl sulfosalt hexafluoro arsenate and poly-(right-tert-butoxy carbonyl oxygen base-α-Jia Jibenyixi).Positive photoresist comprises three components at least: 1) photosensitive acid agent; 2) matrix resin that can acidolysis; 3) solvent.Negative photoresist comprises two classes, and a class is to need crosslinking chemical, the another kind of crosslinking chemical that then do not need.The former comprises four kinds of components at least: 1) photosensitive acid agent; 2) can with the matrix resin of crosslinking chemical phase reaction; 3) crosslinking chemical; 4) solvent.The latter comprises three kinds of components at least: 1) photosensitive acid agent; 2) contain the matrix resin of crosslinked group; 3) solvent.The selection of photosensitive acid agent is an extremely important link in the chemical amplification photoresist.
There has been number of research projects selection aspect at photosensitive acid agent.Concrete, Journal of the OrganicChemistry, 43 (15) (1978) have reported triphenyl sulfosalt derivant.JP7-28237 has reported the alkyl sulfide salt derivative, for example cyclohexyl methyl (the oxo cyclohexyl of 2-) sulfosalt trifluoromethyl sulfonic acid.Journal of the Polymer Science, 56 (1976) have reported diphenyl iodnium and succinimide derivatives.What typically, be widely used in the ArF excimer lithography is the sulfosalt compound.In the photoresist system in past, triphenyl sulfosalt derivant also is as the most frequently used photosensitive acid agent.Concrete, at Journal of Photopolymer Science and Technology, in 10 (4) (1997) and Journal of Photopolymer Science and Technology, 12 (4) (1999) relevant for the report of triphenyl sulfosalt derivant as photosensitive acid agent.
Important techniques main points are to need to have good optical transparency in the short-wavelength light lithography.The defective of optical transparency will cause the reduction and the image inclination of photoresist resolution.In the ArF excimer lithography, the triphenyl sulfosalt does not have desirable effect as photosensitive acid agent, mainly be to have in the triphenyl sulfosalt structure to have benzene ring structure, it has strong absorption in being no more than the far ultraviolet zone of 220nm, and its transparency under the 193nm wavelength is poor.
At above-mentioned technical essential, Proceeding of SPIE has reported two class alkyl sulfide salt compounds, concrete as: the oxo cyclohexyl-methyl of 2--(2-norborny) sulfosalt trifluoromethyl sulfonic acid (NEALS) and cyclohexyl methyl (the oxo cyclohexyl of 2-) sulfosalt trifluoromethyl sulfonic acid (ALS).It has the good transparency under the ArF excimer laser, not enough but it exists in photosensitivity with above the thermal stability.
The present invention relates to the novel sulfosalt compound of a class, it not only can be at ArF and F
2Have the good transparency in the excimer lithography system, also have excellent photosensitivity and thermal stability.
Summary of the invention:, also take all factors into consideration photosensitivity and thermal stability simultaneously in order to solve sulfosalt structure not enough problem of the transparency in 193nm and 157nm photoetching technique.The invention discloses a kind of novel sulfosalt compound that has the thiazolinyl feature structure with general formula I, its can as 193nm and more in the photoresist system under the short wavelength as photosensitive acid agent, and provide preparation method about this general formula I.
Wherein: R
1, R
2Independently be C
1-12Alkyl, or pass through alkylene base structure structure circlewise, abovementioned alkyl or naphthenic base can contain or not contain oxo structure; Z
1Substituent structure for general formula I I; Z
2, Z
3Independently be hydrogen, C
1-6Alkyl, C
1-6Alkoxy, C
3-7Naphthenic base, halogen, C
1-6Alkylhalide group or equal Z
1Z wherein
2, Z
3Do not equal hydrogen simultaneously.R
3, R
4, R
5Independently be hydrogen, the alkyl of straight chain, side chain, monocycle, many rings, crosslinked circular feature, C
1-10Ethylenic unsaturation alkyl or alkynes base; Y
-Representative pairing negative ion.
R in general formula I
1, R
2Circlewise under the situation of group, corresponding sulfosalt compound such as general formula III structure.R is an alkylene base, can have or not have oxo structure in the ring texture.Z
1, Z
2, Z
3, Y
-Define same general formula I.Wherein the cyclic substituents in the general formula III structure is preferably C
4～7Ring can contain or not contain oxo structure.
In the general formula I structure, preferred R
1, R
2Also can be C
1～12Alkyl can contain or not contain oxo structure.
Among the present invention, the pairing negative ion Y among general formula I and the III
-Has Z-SO
3 -, BF
4 -, AsF
6 -, SbF
6 -, ClO
4 -, Br
-, Cl
-, I
-Wherein Z is C
nF
2n+1(n=1～10), alkyl, alkyl replaces or does not have the aryl of alkyl replacement.
The present invention relates to simultaneously and contains general formula I and III positive photoresist composition and the negative photoresist composition as photosensitive acid agent.
The present invention relates to utilize general formula I and III as photosensitive acid agent in the use that is less than or equal under the 300nm wavelength, specifically comprise KrF, ArF, F
2The excimer lithography system.
Usually, formula of I of the present invention and III sulfosalt structural compounds go for the requirement of ArF excimer lithography technology, have excellent optical transparency, have good thermal stability under 150 ℃.
In the general formula I of the present invention, R
1, R
2Can be alkyl or the alkyl that has oxo structure, also can be corresponding ring-type alkylene or the ring-type alkylene that has oxo structure.
Alkyl described herein comprises methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, 2-methyl-butyl, 3-methyl-butyl, 3, the 3-dimethylbutyl, amyl group, 2-methyl amyl, 3-methyl amyl, the 4-methyl amyl, 4,4-dimethyl amyl group, 2-ethyl pentyl group, the 3-ethyl pentyl group, hexyl, 3-methyl hexyl, 4-methyl hexyl, heptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, the 5-methylheptyl, 6-methylheptyl, 6,6-dimethyl heptyl, 2-ethyl heptyl, 3-ethyl heptyl, 4-ethyl heptyl, 5-ethyl heptyl, the 2-propylheptyl, 3-propylheptyl, 4-propylheptyl, octyl group, the 2-Methyl Octyl, 3-Methyl Octyl, 4-Methyl Octyl, 5-Methyl Octyl, the 6-Methyl Octyl, 7-Methyl Octyl, 7,7-dimethyl octyl group, 2-ethyl octyl group, 3-ethyl octyl group, 4-ethyl octyl group, 5-ethyl octyl group, cyclopentyl, cyclohexyl, suberyl, cyclopropyl methyl, the methyl cyclopropyl, cyclohexyl methyl, norborny, three ring decyls (especially three encircle [5.2.1.0
2,6] decyl), adamantyl, bornyl, Fourth Ring dodecyl (Fourth Ring [4.4.0 especially
2,5.1
7,10] dodecyl).
The alkyl that has oxo structure described herein comprises the oxo propyl group of 2-, the oxo butyl of 2-, 2-is oxo-the 3-methyl butyl, 2-oxo-3, the 3-dimethylbutyl, the oxo amyl group of 2-, 2-is oxo-the 3-methyl amyl, 2-oxo-3,3-dimethyl amyl group, 2-is oxo-the 4-methyl amyl, 2-oxo-4,4-dimethyl amyl group, 2-is oxo-the 3-ethyl pentyl group, and 2-is oxo-3,3-diethyl amyl group, 2-is oxo-4-methyl-4-ethyl pentyl group, the oxo hexyl of 2-, 2-is oxo-3-methyl hexyl, 2-oxo-3,3-dimethyl hexyl, 2-is oxo-4,4-dimethyl hexyl, and 2-oxo-5,5-dimethyl hexyl, 2-is oxo-the 3-ethylhexyl, and 2-is oxo-the 4-ethylhexyl, the oxo heptyl of 2-, 2-is oxo-the 3-methylheptyl, 2-is oxo-the 4-methylheptyl, and 2-is oxo-the 5-methylheptyl, and 2-is oxo-the 6-methylheptyl, 2-oxo-6,6-dimethyl heptyl, 2-is oxo-3-ethyl heptyl, and 2-is oxo-4-ethyl heptyl, 2-is oxo-5-ethyl heptyl, 2-is oxo-the 3-propylheptyl, and 2-is oxo-the 4-propylheptyl, the oxo octyl group of 2-, 2-is oxo-the 3-Methyl Octyl, 2-is oxo-the 4-Methyl Octyl, and 2-is oxo-the 5-Methyl Octyl, and 2-is oxo-the 6-Methyl Octyl, 2-is oxo-the 7-Methyl Octyl, 2-is oxo-7,7-dimethyl octyl group, and 2-is oxo-3-ethyl octyl group, 2-is oxo-4-ethyl octyl group, 2-is oxo-5-ethyl octyl group, and the oxo cyclopentyl of 2-, the oxo cyclohexyl of 2-, the oxo suberyl of 2-, 2-is oxo-the cyclopropyl methyl, and 2-is oxo-the methyl cyclopropyl, and 2-is oxo-cyclohexyl methyl, the oxo norbornene of 2-, (especially 2-oxo-three encircles [5.2.1.0 to oxo-three ring decyls of 2-
2,6] decyl), 2-is oxo-the Fourth Ring dodecyl (especially 2-oxo-Fourth Ring [4.4.0.5.1
7,10] dodecyl), the oxo bornyl of 2-, 2-is oxo-2-cyclohexyl ethyl, and 2-is oxo-2-cyclopentyl ethyl.
Ring-type alkylene described here or the ring-type alkylene that has an oxo structure comprise trimethylene, fourth support, pentamethylene, hexamethylene, support in heptan, oxo trimethylene, the support of oxo fourth, oxo pentamethylene, oxo hexamethylene, support in oxo heptan.
In general formula I I, R
3, R
4, R
5Independently be hydrogen, the alkyl that is no more than 12 carbon of straight chain, side chain, monocycle, many rings, crosslinked circular feature, C
1-10Ethylenic unsaturation alkyl or alkynes base.Straight chain, side chain, monocycle, many rings, the alkyl that is no more than 12 carbon of crosslinked circular feature comprises methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, 2-methyl-butyl, 3-methyl-butyl, 3,3-dimethylbutyl, amyl group, the 2-methyl amyl, 3-methyl amyl, 4-methyl amyl, 4,4-dimethyl amyl group, 2-ethyl pentyl group, the 3-ethyl pentyl group, hexyl, 3-methyl hexyl, 4-methyl hexyl, heptyl, 2-methylheptyl, the 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, the 6-methylheptyl, 6,6-dimethyl heptyl, 2-ethyl heptyl, 3-ethyl heptyl, 4-ethyl heptyl, 5-ethyl heptyl, 2-propylheptyl, 3-propylheptyl, the 4-propylheptyl, octyl group, 2-Methyl Octyl, the 3-Methyl Octyl, 4-Methyl Octyl, 5-Methyl Octyl, the 6-Methyl Octyl, 7-Methyl Octyl, 7,7-dimethyl octyl group, 2-ethyl octyl group, 3-ethyl octyl group, 4-ethyl octyl group, 5-ethyl octyl group, cyclopentyl, cyclohexyl, suberyl, cyclopropyl methyl, the methyl cyclopropyl, cyclohexyl methyl, norborny, three ring decyls (especially three encircle [5.2.1.0
2,6] decyl), adamantyl, bornyl, Fourth Ring dodecyl (Fourth Ring [4.4.0 especially
2,5.1
7,10] dodecyl).
The corresponding pairing of Y-representative negative ion.Y-pairing negative ion comprises BF among the present invention
4 -AsF
6 -SbF
6 -Contain the sulfonic acid anion of fluorocarbon group, comprise CF
3SO
3 -, C
2F
5SO
3 -, C
3F
7SO
3 -, C
4F
9SO
3 -, C
5F
11SO
3 -, C
6F
13SO
3 -, C
7F
15SO
3 -, C
8F
17SO
3 -, C
9F
19SO
3 -, C
10F
21SO
3 -The alkyl sulfonic acid negative ion comprises CH
3SO
3 -, C
2H
5SO
3 -, C
3H
7SO
3 -, C
4H
9SO
3 -, C
5H
11SO
3 -, C
6H
13SO
3 -, C
7H
15SO
3 -, C
8H
17SO
3 -, cyclohexyl sulfonate radical, camphorsulfonic acid root; The sulfonic acid anion that has aromatic ring shape structure comprises the benzene sulfonic acid root, tosylate, naphthalene sulfonic acids root, fluorobenzene sulfonate radical, difluoro benzene sulfonic acid root, trifluoro-benzene sulfonate radical, chlorobenzenesulfonic acid root, dichloro benzosulfonic acid root, trichloro-benzenes sulfonate radical; ClO
4 -Cl
-Br
-I
-
The present invention relates to the preparation method of synthetic general formula I sulfosalt compound.General formula I sulfosalt compound passes through general formula I V sulfide:
R
1-S-R
2 IV
In general formula I V, R
1, R
2The same general formula I of definition.
General formula I V sulfide is dissolved in the acetonitrile, carries out condensation with the halogenated alkyl compounds of general formula V again.
In general formula V, Z
1, Z
2, Z
3The same general formula I of definition; X represents halogen, comprises iodine, bromine, chlorine.
After stirring 0.5～24 hour, react with general formula VI organometallics again.
Y
-W
+VI
In general formula VI, the same general formula I of the definition of Y; W is a metallic atom, comprises potassium, sodium and silver.
In course of reaction, halogen metal compound salt precipitation can remove by the method for filtering, and residue can obtain general formula I sulfosalt compound by the mode of solvent rinsing or recrystallization.
Formula of I sulfosalt compound of the present invention is a noval chemical compound, itself and known triphenyl sulfosalt trifluoromethyl sulfonic acid (abbreviation: TPS) compare, have lower light absorption in ArF excimer lithography system.To be that the extreme ultraviolet zone of representative often more in the ArF excimer laser have a very strong light absorption to known photosensitive acid agent (as TPS) at KrF excimer lithography system; Accordingly, there is obvious defects in its pairing photoresist transparency under the ArF situation.Compare with TPS, formula of I sulfosalt compound of the present invention as photosensitive acid agent in the ArF photoetching, have seldom light absorption and the high transparency, be applicable to the ArF photoresist.Simultaneously, compound of Formula I of the present invention is as photosensitive acid agent, and it is at KrF and F
2Also have the high transparency under the excimer laser situation, go for corresponding photoresist.
Compare and the oxo cyclohexyl-methyl of top 2--(2-norborny) sulfosalt trifluoromethyl sulfonic acid (NEALS) and cyclohexyl methyl (the oxo cyclohexyl of 2-) sulfosalt trifluoromethyl sulfonic acid (ALS), formula of I sulfosalt compound of the present invention has higher photosensitivity, higher thermal decomposition point and more excellent thermal stability.
According to the description of front, the chemical amplification photoetching compositions that relates among the present invention divides positive photoresist and negative photoresist.Positive photoresist comprises three components at least: 1) photosensitive acid agent; 2) matrix resin that can acidolysis; 3) solvent.Negative photoresist comprises two classes, and a class is to need crosslinking chemical, the another kind of crosslinking chemical that then do not need.The former comprises four kinds of components at least: 1) photosensitive acid agent; 2) can with the matrix resin of crosslinking chemical phase reaction; 3) crosslinking chemical; 4) solvent.The latter comprises three kinds of components at least: 1) photosensitive acid agent; 2) contain the matrix resin of crosslinked group; 3) solvent.
In the photoetching compositions that relates among the present invention, general formula I sulfosalt compound can use separately, or uses with two or more other photosensitive acid agent merging.In photoresist of the present invention, the content of general formula I sulfosalt compound in whole solid constituent is 0.1-40% (wt.), is preferably 1-25% (wt.).If content is lower than 0.1% (wt.), the photosensitivity of photoresist will descend, and photoetching process is difficult to realize; If content is higher than 40% (wt.), the formation difficulty of uniform coating forms residue and scum silica frost easily.
Among the present invention, in the photoetching compositions of extreme ultraviolet zone, can adopt the polymkeric substance of common report in the selection of matrix resin.In the positive photoresist composition, resin must have the good transparency under exposure wavelength, can make that its dissolubility obtains discharging by acid hydrolysis simultaneously in alkaline diffusant.In the photoresist combination does not have, remove in the component after desolvating, the content of resin is preferably 75-99% (wt.) at 60-99.8% (wt.).
Concrete resin can be as the general formula VII polymkeric substance of JP2000-26446 report.
Wherein: R
6, R
7, R
8, R
10Independently be hydrogen, methyl; R
9Be the acidolysis group, the C of acid decomposable
7-13Bridged cyclic hydrocarbon group; R
11Be hydrogen, C
1-12Alkyl has the C of carbonyl
7-13Bridged cyclic hydrocarbon group; X, y, z satisfies x+y+z=1,0＜x＜1,0＜y＜1,0≤z＜1; The mean molecular weight of polymkeric substance (wt) 2000～200000.
Another kind of resin can be the general formula VIII polymkeric substance of JP2856116 report.
Wherein: R
12, R
13, R
14Independently be hydrogen, methyl; M is the C of acid decomposable
7-13Bridged cyclic hydrocarbon group; R
15It is the acidolysis group; R
16Be hydrogen, C
1-12Alkyl; K, m, n satisfies x+y+z=1,0＜k＜1,0＜m＜1,0≤n＜1; The mean molecular weight of polymkeric substance (wt) 2000～200000.
A resinoid such as Journal of Photopolymer Science and Technology again, the general formula I X polymkeric substance of 10 (4) (1997) reports.
Wherein: R
17, R
18, R
19Independently be hydrogen, methyl; R
20It is a group with lactone structure; A, b satisfies a+b=1,0＜a＜1,0＜b＜1; The mean molecular weight of polymkeric substance (wt) 2000～200000.
One resinoid such as Journal of Photopolymer Science and Technology are arranged again, the general formula X polymkeric substance of 10 (3) (1997) reports.
Wherein: c, d, e satisfies c+d+e=1,0≤c＜1,0＜d＜1,0＜e＜1; The mean molecular weight of polymkeric substance (wt) 2000～200000.
In the negative photoresist composition, resin must have the good transparency under exposure wavelength among the present invention, can have insoluble characteristic by acid hydrolysis simultaneously in alkaline diffusant.In the photoresist combination does not have, remove in the component after desolvating, the content of resin is preferably 75-99% (wt.) at 60-99.8% (wt.).
Concrete resin can be Journal of Photopolymer Science and Technology, the general formula X I polymkeric substance of 12 (3) (1999) reports.
Wherein: i, j, k satisfies i+j+k=1,0≤i＜1,0＜j＜1,0＜k＜1; The mean molecular weight of polymkeric substance (wt) 2000～200000.Another kind of resin can general formula X II polymkeric substance.
Wherein: l, m, n satisfies l+m+n=1,0≤l＜1,0＜m＜1,0＜n＜1; Polymkeric substance mean molecular weight (wt) 2000～200000.
In the negative photoresist composition, need to use crosslinking chemical, preferred cross-linking agents can be urea-melamine system or multiple functional radical epoxy compound, for example HMMM, 1,3,4,6-four (methoxy) glycoluril, 1, two (methoxy) ureas of 3-.The selection of crosslinking chemical is not limited to above-mentioned kind, can be independent use, also can be that two or more merge use.
Polyvalent alcohol can comprise 2,3-dihydroxy-5-hydroxyl norcamphane, 1,4-cyclohexyl dimethanol, 3,4,8 (9)-trialkyl tristanes as the promoter of crosslinking chemical.
Being suitable for solvent of the present invention can be numerous species, and it is effective dissolubility that must improve the composition that comprises polymkeric substance and sulfosalt, and makes that final being honoured with can be in order to form uniform coating.Solvent can use separately, also can be that two or more merge use.Particularly, can comprise n-propanol, isopropyl alcohol, normal butyl alcohol, the tert-butyl alcohol, propyleneglycoles list ethylether acetic acid esters, methyl lactate, ethyl lactate, 2-methoxyl butylacetic acid ester, 2-ethoxyethyl group acetic acid esters, methyl pyruvate, ethyl acetone acid esters, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, N-Methyl pyrrolidone, cyclohexane, cyclopentanol, cyclohexanol, methyl ethyl ketone, 1, the 4-dioxane.Choice of Solvent is not limited to above-mentioned kind.
In the photoetching compositions, if necessary, can contain other component among the present invention, comprise surfactant, pigment, stabilizing agent, levelling agent and dyestuff.Diffusant can comprise appropriate organic solvent, the potpourri of organic solvent, water aqueous slkali or itself and the formed potpourri of organic solvent.Under the necessary situation, can consider in diffusant, to add surfactant.The volume solvent that is fit to comprises acetone, methyl ethyl ketone, methyl alcohol, ethanol, isopropyl alcohol, tetrahydrofuran, dioxane.Alkaline solution or aqueous solution can be inorganic bases, comprise NaOH, potassium hydroxide, sodium silicate and ammoniacal liquor; Can be organic base, comprise ethamine, propylamine, diethylamine, di-n-propylamine, trimethylamine, triethylamine; Can be organic ammonium salt also, comprise Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, trimethyl methylol ammonium hydroxide, triethyl methylol ammonium hydroxide, trimethyl hydroxyethylammoniumhydroxide hydroxide.The selection of above-mentioned solvent and alkaline solution is not limited to top category.
Following example will describe the present invention in detail, but in no case limit the scope of the invention.The preparation that instantiation is mainly concerned with general formula I sulfosalt derivant with and as the application of photosensitive acid agent in the photoresist system.
Embodiment:
Preparation embodiment one:
1, the preparation (target compound 1) of 2-dimethyl-2-propenyl-sulfo-cyclopentane salt trifluoromethyl sulfonic acid
Whole synthetic operation need carry out under yellow light.
In the reaction vessel that stirring, thermometer and reflux condensing tube are housed, the 2g thiophane is dissolved in the 40ml acetonitrile, under stirring condition, with 2.1g3-bromo-2,3-dimethyl-propylene is added drop-wise in the reaction system and goes then.After stirring 1 hour, add 3.6g trifluoromethane sulfonic acid potassium and 40ml acetonitrile.Continue to stir 3 hours, decompression removes solvent behind the filtering potassium bromide, and residue washs with ether, utilize acetone-ether system carry out crystallization handle white solid.After filtration, obtain target product 1.Productive rate 70%.
By
1HNMR,
13CNMR and MS test illustrate that target product meets 1, the architectural characteristic of 2-dimethyl-2-propenyl-sulfo-cyclopentane salt trifluoromethyl sulfonic acid.
Concrete ultimate analysis situation is as follows: measured value (calculated value) C39.11% (39.22%); H5.53% (5.55%); F18.59 (18.62%).
Preparation embodiment two:
1, the preparation (target compound 2) of 2-dimethyl-2-propenyl-sulfo-cyclohexane monohydrochloride trifluoromethyl sulfonic acid
1, the preparation of 2-dimethyl-2-propenyl-sulfo-cyclohexane monohydrochloride trifluoromethyl sulfonic acid is similar to preparation embodiment one, and initial feed is the thiophane in the alternative preparation example one of pentamethylene sulfide.This target compound 2 is a white solid.
By
1HNMR,
13CNMR and MS test illustrate that target product meets 1, the architectural characteristic of 2-dimethyl-2-propenyl-sulfo-cyclohexane monohydrochloride trifluoromethyl sulfonic acid.
Concrete ultimate analysis situation is as follows: measured value (calculated value) C41.18% (41.25%); H5.95% (5.94%); F17.75 (17.81%).
Preparation embodiment three:
1, the preparation (target compound 3) of 2-dimethyl-2-propenyl-sulfo-cyclopentane salt nine fluorine butyl sulfosalts
1, the preparation of 2-dimethyl-2-propenyl-sulfo-cyclopentane salt nine fluorine butyl sulfosalts is similar to preparation embodiment one, uses nine fluorine butyl sulfonic acid potassium instead and substitutes trifluoromethane sulfonic acid potassium.This target compound 3 is a white solid.
By
1HNMR,
13CNMR and MS test illustrate that target product meets 1, the architectural characteristic of 2-dimethyl-2-propenyl-sulfo-cyclopentane salt nine fluorine butyl sulfosalts.
Concrete ultimate analysis situation is as follows: measured value (calculated value) C34.01% (34.21%); H3.75% (3.73%); F37.68% (37.50%).
Preparation embodiment four:
The preparation (target compound 4) of 1-methyl-2-butene base-sulfo-cyclopentane salt trifluoromethyl sulfonic acid
In the reaction vessel that stirring, thermometer and reflux condensing tube are housed, the 2g thiophane is dissolved in the 40ml acetonitrile, then under stirring condition, 3g4-bromo-4-methyl-2-butene is added drop-wise in the reaction system goes.After stirring 1 hour, add 4g trifluoromethane sulfonic acid potassium and 40ml acetonitrile.Continue to stir 3 hours, decompression removes solvent behind the filtering potassium bromide, and residue washs with ether, utilize acetone-ether system carry out crystallization handle white solid.After filtration, obtain target product 4.Productive rate 71%.
By
1HNMR,
13CNMR and MS test illustrate that target product meets the architectural characteristic of 1-methyl-2-butene base-sulfo-cyclopentane salt trifluoromethyl sulfonic acid.
Concrete ultimate analysis situation is as follows: measured value (calculated value) C39.13% (39.22%); H5.58% (5.55%); F18.57 (18.62%).
Preparation embodiment five:
1, the preparation (target compound 5) of 3-dimethyl-2-butenyl group-sulfo-cyclopentane salt trifluoromethyl sulfonic acid
In the reaction vessel that stirring, thermometer and reflux condensing tube are housed, the 2g thiophane is dissolved in the 40ml acetonitrile, under stirring condition, with 3.2g4-bromo-2,4-dimethyl-2-butylene is added drop-wise in the reaction system and goes then.After stirring 1 hour, add 4.2g trifluoromethane sulfonic acid potassium and 40ml acetonitrile.Continue to stir 3 hours, decompression removes solvent behind the filtering potassium bromide, and residue washs with ether, utilize acetone-ether system carry out crystallization handle white solid.After filtration, obtain target product 5.Productive rate 72%.
By
1HNMR,
13CNMR and MS test illustrate that target product meets 1, the architectural characteristic of 3-dimethyl-2-butenyl group-sulfo-cyclopentane salt trifluoromethyl sulfonic acid.
Concrete ultimate analysis situation is as follows: measured value (calculated value) C41.21% (41.25%); H5.97% (5.94%); F17.78 (17.81%).
Preparation embodiment six:
1, the preparation (target compound 6) of 1-two (propylene-2-yl) methyl-sulfo-cyclopentane salt trifluoromethyl sulfonic acid
1, the preparation of 1-two (propylene-2-yl) methyl-sulfo-cyclopentane salt trifluoromethyl sulfonic acid is similar to be preparation embodiment one, uses 3-bromo-2 instead, 4-dimethyl-1, and the 4-cinene substitutes 3-bromo-2,3-dimethyl-propylene.This target compound 4 is a white solid.
By
1HNMR,
13CNMR and MS test illustrate that target product meets 1, the architectural characteristic of 1-two (propylene-2-yl) methyl-sulfo-cyclopentane salt trifluoromethyl sulfonic acid.
Concrete ultimate analysis situation is as follows: measured value (calculated value) C43.31% (43.37%); H5.75% (5.72%); F17.18% (17.17%).
Preparation embodiment seven:
1, the preparation (target compound 7) of 2-dimethyl-2-propenyl-diethyl sulfosalt trifluoromethyl sulfonic acid
In the reaction vessel that stirring, thermometer and reflux condensing tube are housed, the 1.5g diethyl sulfide is dissolved in the 40ml acetonitrile, under stirring condition, with 2.1g3-bromo-2,3-dimethyl-propylene is added drop-wise in the reaction system and goes then.After stirring 1 hour, add 3.8g trifluoromethane sulfonic acid potassium and 40ml acetonitrile.Continue to stir 3 hours, decompression removes solvent behind the filtering potassium bromide, and residue washs with ether, utilize acetone-ether system carry out crystallization handle white solid.After filtration, obtain target product 7.Productive rate 71%.
By
1HNMR,
13CNMR and MS test illustrate that target product meets 1, the architectural characteristic of 2-dimethyl-2-propenyl-diethyl sulfosalt trifluoromethyl sulfonic acid.
Concrete ultimate analysis situation is as follows: measured value (calculated value) C39.19% (39.22%); H5.54% (5.55%); F18.64 (18.62%).
The Application Example part:
Application Example 1: the thermal stability evaluation on the resinite coating
The photosensitive acid agent (preparation example 1-7 target compound) that will contain the polymkeric substance and 1% (wt.) of 40% methyl methacrylate+40% tert-butyl group methacrylate+20% methacrylic acid is made 0.4 μ m thin layer.Heating is 60 seconds in the well heater of predetermined temperature, rapidly behind the cool to room temperature, (Tetramethylammonium hydroxide TMAH) is immersed processing with the alkaline diffusant of 2.38% (wt.) again, as the result of assessment, the decomposition temperature of corresponding photosensitive acid agent as shown in Table 1.
The principle of its mensuration is: under certain specific decomposition temperature, photosensitive acid agent will cause it to be dissolved in diffusant to the acidolysis radical reaction in the resinous polymer after decomposing.
Should be with the mensuration of simultaneously the oxo cyclohexyl-methyl of 2-(2-norborny) sulfosalt trifluoromethyl sulfonic acid (NEALS) having been carried out comparative among the embodiment.
Table 1
| Photosensitive acid agent | The decomposition point temperature |
| Target compound 1 | 160℃ |
| Target compound 2 | 158℃ |
| Target compound 3 | 156℃ |
| Target compound 4 | 160℃ |
| Target compound 5 | 158℃ |
| Target compound 6 | 159℃ |
| Target compound 7 | 161℃ |
| NEALS | 125℃ |
Application Example 2: utilize sulfosalt among the present invention to make the positive photoresist Performance Evaluation of photosensitive acid agent
Containing the photoetching compositions of following component:
A) 2g has the resin of following paradigmatic structure
B) the photosensitive acid agent of 0.02g (according to the above-mentioned resulting target compound 1-7 of preparation embodiment 1-7)
C) 11.5g propenyl ethylene glycol monomethyl ether acetate
Said mixture prepares corresponding photoresist after filtering with 0.2 μ mTeflon filtrator.Coating was cured 1 minute at 130 ℃ on 4 o'clock silicon chips, formed the shallow layer of 0.4 μ m thickness.This wafer that has photoresist coating is placed in the contact-type exposure sources that is full of nitrogen reposefully.After covering the mask of layout on the piezoid, expose by the ArF excimer laser.In 110 ℃ of well heaters, cured 60 seconds behind the end exposure.Be immersed in 23 ℃ the alkaline diffusant of 2.38% (wt.) (Tetramethylammonium hydroxide, TMAH) in, used the pure water rinsing then 60 seconds.And then obtain corresponding positivity photoengraving pattern.
The mensuration of comparative has been carried out in experiment as a comparison to the oxo cyclohexyl-methyl of 2-(2-norborny) sulfosalt trifluoromethyl sulfonic acid (NEALS) and triphenyl sulfosalt trifluoromethyl sulfonic acid (TPS).
Table 2 has shown the result of photosensitivity and resolution.Can find out clearly that from table 2 the photosensitive acid agent of sulfosalt of the present invention is used for positive photoresist can have better resolution and photosensitivity.
Table 2
| Photoetching compositions | Resolution (μ mL/s) | Photosensitivity (mJ/cm 3) |
| The photoresist that contains target compound 1 | 0.17 | 7.9 |
| The photoresist that contains target compound 2 | 0.17 | 7.7 |
| The photoresist that contains target compound 3 | 0.17 | 7.8 |
| The photoresist that contains target compound 4 | 0.17 | 7.9 |
| The photoresist that contains target compound 5 | 0.17 | 8.0. |
| The photoresist that contains target compound 6 | 0.16 | 7.5 |
| The photoresist that contains target compound 7 | 0.17 | 8.5 |
| The photoresist that contains NEALS | 0.19 | 53 |
| The photoresist that contains TPS | 0.19 | 7.2 |
Application Example 3: utilize sulfosalt among the present invention to make the negative photoresist Performance Evaluation of photosensitive acid agent
Containing the photoetching compositions of following component:
A) 2g has the resin of following paradigmatic structure
B) the photosensitive acid agent of 0.04g (according to the above-mentioned resulting target compound 1-7 of preparation embodiment 1-7)
C) 0.3g2,3-dihydroxy-5-methylol norcamphane
D) 11.5g ethyl acetate
Said mixture prepares corresponding photoresist after filtering with 0.2 μ mTeflon filtrator.Coating was cured 1 minute at 80 ℃ on 4 o'clock silicon chips, formed the shallow layer of 0.4 μ m thickness.This wafer that has photoresist coating is placed in the contact-type exposure sources that is full of nitrogen reposefully.After covering the mask of layout on the piezoid, expose by the ArF excimer laser.In 130 ℃ of well heaters, cured 60 seconds behind the end exposure.Be immersed in 23 ℃ the alkaline diffusant of 2.38% (wt.) (Tetramethylammonium hydroxide, TMAH) in, used the pure water rinsing then 60 seconds.And then obtain corresponding negativity photoengraving pattern.
The mensuration of comparative has been carried out in experiment as a comparison to the oxo cyclohexyl-methyl of 2-(2-norborny) sulfosalt trifluoromethyl sulfonic acid (NEALS) and triphenyl sulfosalt trifluoromethyl sulfonic acid (TPS).
Table 3 has shown the result of photosensitivity and resolution.Can find out clearly that from table 3 the photosensitive acid agent of sulfosalt of the present invention is used for negative photoresist can have better resolution and photosensitivity.
Table 3
| Photoetching compositions | Resolution (μ mL/s) | Photosensitivity (mJ/cm 3) |
| The photoresist that contains target compound 1 | 0.18 | 7.8 |
| The photoresist that contains target compound 2 | 0.18 | 7.7 |
| The photoresist that contains target compound 3 | 0.18 | 7.6 |
| The photoresist that contains target compound 4 | 0.18 | 7.7 |
| The photoresist that contains target compound 5 | 0.18 | 7.9. |
| The photoresist that contains target compound 6 | 0.17 | 7.2 |
| The photoresist that contains target compound 7 | 0.18 | 8.2 |
| The photoresist that contains NEALS | 0.20 | 50 |
| The photoresist that contains TPS | 0.19 | 7.1 |
Commercial Application:
Pass through the above embodiments, according to sulfosalt target compound related among the present invention as photosensitive acid agent, corresponding photoetching compositions and the photoetching method that utilizes photoetching compositions to obtain, can have in the far ultraviolet zone excellent light transmission, be particularly useful in the photoetching technique of ArF PRK. Target compound of the present invention can obtain excellent resolution ratio as photosensitive acid agent simultaneously.
Claims (9)
1. sulfosalt derivant is characterized in that it is that general formula is the compound of I:
Wherein: R
1, R
2Independently be C
1-12Alkyl, or pass through alkylene base structure structure circlewise, abovementioned alkyl or naphthenic base can contain or not contain oxo structure; Z
1Substituent structure for general formula I I; Z
2, Z
3Independently be hydrogen, C
1-6Alkyl, C
1-6Alkoxy, C
3-7Naphthenic base, halogen, C
1-6Alkylhalide group or equal Z
1Z wherein
2, Z
3Do not equal hydrogen simultaneously.R
3, R
4, R
5Independently be hydrogen, the alkyl of straight chain, side chain, monocycle, many rings, crosslinked circular feature, C
1-10Ethylenic unsaturation alkyl or alkynes base; Y
-Representative pairing negative ion.
2. sulfosalt derivant is characterized in that it is that general formula is the compound of III:
Wherein: R is an alkylene base, can have or not have oxo structure in the ring texture.Z
1Substituent structure for general formula I I; Z
2, Z
3Independently be hydrogen, C
1-6Alkyl, C
1-6Alkoxy, C
3-7Naphthenic base, halogen, C
1-6Alkylhalide group or equal Z
1Z wherein
2, Z
3Do not equal hydrogen simultaneously.R
3, R
4, R
5Independently be hydrogen, the alkyl of straight chain, side chain, monocycle, many rings, crosslinked circular feature, C
1-10Ethylenic unsaturation alkyl or alkynes base; Y
-Representative pairing negative ion.
3. as claim 1 and 2, a kind of sulfosalt derivant is characterized by the pairing negative ion Y among general formula I and the III
-Has Z-SO
3 -, BF
4 -, AsF
6 -, SbF
6 -, ClO
4 -, Br
-, Cl
-, I
-Wherein Z is C
nF
2n+1(n=1～10), alkyl, alkyl replaces or does not have the aryl of alkyl replacement.
4. as claim 1 and 3, one positive photoresists, containing a kind of photosensitive acid agent at least is compound of Formula I.
5. as claim 1 and 3, one negative photoresists, containing a kind of photosensitive acid agent at least is compound of Formula I.
6. as claim 2 and 3, one positive photoresists, containing a kind of photosensitive acid agent at least is compound of formula III.
7. as claim 2 and 3, one negative photoresists, containing a kind of photosensitive acid agent at least is compound of formula III.
8. as claim 4,5,6 and 7, photoresist is applied to the occasion smaller or equal to the 300nm exposure wavelength.
9. as claim 4,5,6,7 and 8, photoresist is used in KrF, ArF, F
2The occasion of excimer laser exposure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510038661 CN1727997A (en) | 2005-04-01 | 2005-04-01 | Novel sulfonium salt compound capable of being used as photosensitive acid generator and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510038661 CN1727997A (en) | 2005-04-01 | 2005-04-01 | Novel sulfonium salt compound capable of being used as photosensitive acid generator and preparation method thereof |
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| Publication Number | Publication Date |
|---|---|
| CN1727997A true CN1727997A (en) | 2006-02-01 |
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ID=35927332
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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| Country | Link |
|---|---|
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011026300A (en) * | 2009-06-23 | 2011-02-10 | Sumitomo Chemical Co Ltd | Salt for acid generator of resist composition |
| CN103913950A (en) * | 2012-12-31 | 2014-07-09 | 东友精细化工有限公司 | Photosensitive resin composition and insulating layer manufactured from the same |
| CN104076601A (en) * | 2013-03-30 | 2014-10-01 | 罗门哈斯电子材料有限公司 | Acid generators and photoresists comprising same |
-
2005
- 2005-04-01 CN CN 200510038661 patent/CN1727997A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011026300A (en) * | 2009-06-23 | 2011-02-10 | Sumitomo Chemical Co Ltd | Salt for acid generator of resist composition |
| CN103913950A (en) * | 2012-12-31 | 2014-07-09 | 东友精细化工有限公司 | Photosensitive resin composition and insulating layer manufactured from the same |
| CN104076601A (en) * | 2013-03-30 | 2014-10-01 | 罗门哈斯电子材料有限公司 | Acid generators and photoresists comprising same |
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