CN1636971A - 肟衍生物及其作为潜酸的用途 - Google Patents
肟衍生物及其作为潜酸的用途 Download PDFInfo
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- CN1636971A CN1636971A CNA2004100925757A CN200410092575A CN1636971A CN 1636971 A CN1636971 A CN 1636971A CN A2004100925757 A CNA2004100925757 A CN A2004100925757A CN 200410092575 A CN200410092575 A CN 200410092575A CN 1636971 A CN1636971 A CN 1636971A
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- CN
- China
- Prior art keywords
- acid
- phenyl
- substituted
- alkyl
- compounds
- Prior art date
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- 150000002923 oximes Chemical class 0.000 title claims abstract description 44
- 239000002253 acid Substances 0.000 title abstract description 63
- 150000007513 acids Chemical class 0.000 title abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 43
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000006331 halo benzoyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 5
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical compound [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 claims 1
- -1 anthracyl Chemical group 0.000 abstract description 132
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 36
- 239000001257 hydrogen Substances 0.000 abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 8
- 125000004957 naphthylene group Chemical group 0.000 abstract description 5
- 125000005561 phenanthryl group Chemical group 0.000 abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 89
- 150000001875 compounds Chemical class 0.000 description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000000576 coating method Methods 0.000 description 39
- 150000003254 radicals Chemical class 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- 239000011248 coating agent Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 25
- 239000011347 resin Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006467 substitution reaction Methods 0.000 description 18
- 239000011230 binding agent Substances 0.000 description 16
- 238000001723 curing Methods 0.000 description 16
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 16
- 230000005855 radiation Effects 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000004132 cross linking Methods 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 150000002367 halogens Chemical class 0.000 description 13
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 229920000877 Melamine resin Polymers 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 230000001678 irradiating effect Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 7
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 7
- 229920000178 Acrylic resin Polymers 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- 229920001225 polyester resin Polymers 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 229920001568 phenolic resin Polymers 0.000 description 6
- 239000011780 sodium chloride 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
- 239000004925 Acrylic resin Substances 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000004645 polyester resin Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SIBMDYHEOZTGEU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-2-(4-hydroxyiminocyclohexa-2,5-dien-1-ylidene)acetonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C(C#N)=C1C=CC(=NO)C=C1 SIBMDYHEOZTGEU-UHFFFAOYSA-N 0.000 description 4
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 238000007171 acid catalysis Methods 0.000 description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 3
- KGENPKAWPRUNIG-UHFFFAOYSA-N 1-[chloro(ethyl)phosphoryl]ethane Chemical compound CCP(Cl)(=O)CC KGENPKAWPRUNIG-UHFFFAOYSA-N 0.000 description 3
- FFMCLBWUYMDFEE-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-(4-hydroxyiminocyclohexa-2,5-dien-1-ylidene)acetonitrile Chemical compound C1=CC(=NO)C=CC1=C(C#N)C1=CC=C(Cl)C=C1Cl FFMCLBWUYMDFEE-UHFFFAOYSA-N 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
- 238000004679 31P NMR spectroscopy Methods 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 239000004642 Polyimide Substances 0.000 description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
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- 150000001412 amines Chemical class 0.000 description 3
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
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- 150000002978 peroxides Chemical class 0.000 description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
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- 239000002243 precursor Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
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- JMUOXOJMXILBTE-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 JMUOXOJMXILBTE-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
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- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
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- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
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- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GJWMYLFHBXEWNZ-UHFFFAOYSA-N tert-butyl (4-ethenylphenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(C=C)C=C1 GJWMYLFHBXEWNZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
- C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- 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
- Y10S430/114—Initiator 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
- Y10S430/114—Initiator containing
- Y10S430/117—Free radical
-
- 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
- Y10S430/114—Initiator containing
- Y10S430/12—Nitrogen compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98811084 | 1998-10-29 | ||
| EP98811084.7 | 1998-10-29 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB99812849XA Division CN1205215C (zh) | 1998-10-29 | 1999-10-18 | 肟衍生物及其作为潜酸的用途 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1636971A true CN1636971A (zh) | 2005-07-13 |
Family
ID=8236416
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2004100925757A Pending CN1636971A (zh) | 1998-10-29 | 1999-10-18 | 肟衍生物及其作为潜酸的用途 |
| CNB99812849XA Expired - Fee Related CN1205215C (zh) | 1998-10-29 | 1999-10-18 | 肟衍生物及其作为潜酸的用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB99812849XA Expired - Fee Related CN1205215C (zh) | 1998-10-29 | 1999-10-18 | 肟衍生物及其作为潜酸的用途 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6485886B1 (enExample) |
| EP (1) | EP1124832B1 (enExample) |
| JP (1) | JP2002528550A (enExample) |
| KR (1) | KR100634037B1 (enExample) |
| CN (2) | CN1636971A (enExample) |
| AU (1) | AU6340899A (enExample) |
| DE (1) | DE69904073T2 (enExample) |
| WO (1) | WO2000026219A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN120737322A (zh) * | 2025-09-02 | 2025-10-03 | 西北工业大学 | 一种基于手性主链的液晶聚合物及其制备方法和应用 |
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|---|---|---|---|---|
| EP1124832B1 (en) * | 1998-10-29 | 2002-11-20 | Ciba SC Holding AG | Oxime derivatives and the use thereof as latent acids |
| NL1014545C2 (nl) * | 1999-03-31 | 2002-02-26 | Ciba Sc Holding Ag | Oxim-derivaten en de toepassing daarvan als latente zuren. |
| ATE288907T1 (de) * | 2001-06-01 | 2005-02-15 | Ciba Sc Holding Ag | Substituierte oxim-derivate und ihre verwendung als latente säuren |
| US7098463B2 (en) * | 2003-03-03 | 2006-08-29 | Heuris Pharma, Llc | Three-dimensional dosimeter for penetrating radiation and method of use |
| WO2004081664A2 (en) * | 2003-03-11 | 2004-09-23 | Arch Specialty Chemicals, Inc. | Novel photosensitive resin compositions |
| US20070020793A1 (en) * | 2004-03-01 | 2007-01-25 | Adamovics John A | Three-dimensional shaped solid dosimeter and method of use |
| JP2008506826A (ja) * | 2004-07-21 | 2008-03-06 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 光活性化方法及び逆転した２段階工程による触媒の使用 |
| JP4548617B2 (ja) * | 2006-06-09 | 2010-09-22 | 信越化学工業株式会社 | 化学増幅レジスト材料用光酸発生剤、及び該光酸発生剤を含有するレジスト材料、並びにこれを用いたパターン形成方法 |
| US8466096B2 (en) * | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
| GB2450975B (en) | 2007-07-12 | 2010-02-24 | Ciba Holding Inc | Yellow radiation curing inks |
| JP2012522084A (ja) | 2009-03-30 | 2012-09-20 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｕｖ線量インジケータフィルム |
| WO2011032998A1 (en) * | 2009-09-18 | 2011-03-24 | Loctite (R&D) Limited | Phosphonate bonding compositions |
| US9145383B2 (en) | 2012-08-10 | 2015-09-29 | Hallstar Innovations Corp. | Compositions, apparatus, systems, and methods for resolving electronic excited states |
| WO2014025370A1 (en) | 2012-08-10 | 2014-02-13 | Hallstar Innovations Corp. | Tricyclic energy quencher compounds for reducing singlet oxygen generation |
| US9125829B2 (en) | 2012-08-17 | 2015-09-08 | Hallstar Innovations Corp. | Method of photostabilizing UV absorbers, particularly dibenzyolmethane derivatives, e.g., Avobenzone, with cyano-containing fused tricyclic compounds |
| JP6599446B2 (ja) | 2014-05-30 | 2019-10-30 | アイジーエム レシンス イタリア ソチエタ レスポンサビリタ リミタータ | 多官能性アシルホスフィンオキシド光重合開始剤 |
| MX375374B (es) | 2015-04-29 | 2025-03-06 | Bsn Medical Gmbh | Dispositivo de baño médico. |
| CA2984044A1 (en) | 2015-04-29 | 2016-11-03 | Bsn Medical Gmbh | Steady-state no production via ph control |
| DE102016111590A1 (de) | 2016-06-24 | 2017-12-28 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Einkomponentenmasse auf Basis von Alkoxysilanen und Verfahren zum Fügen oder Vergießen von Bauteilen unter Verwendung der Masse |
| WO2018155547A1 (ja) * | 2017-02-23 | 2018-08-30 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性樹脂組成物、硬化パターンの製造方法、硬化物、層間絶縁膜、カバーコート層、表面保護膜、及び電子部品 |
| DE102017126215A1 (de) | 2017-11-09 | 2019-05-09 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Verfahren zur Erzeugung opaker Beschichtungen, Verklebungen und Vergüsse sowie härtbare Masse zur Verwendung in dem Verfahren |
| WO2020031240A1 (ja) | 2018-08-06 | 2020-02-13 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性樹脂組成物、パターン硬化膜の製造方法、硬化膜、層間絶縁膜、カバーコート層、表面保護膜及び電子部品 |
| WO2020049378A1 (en) | 2018-09-07 | 2020-03-12 | Igm Resins Italia S.R.L. | Multifunctional bisacylphosphine oxide photoinitiators |
| DE102018127854A1 (de) | 2018-11-08 | 2020-05-14 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Feuchtigkeitshärtbare Einkomponentenmasse und Verfahren zum Fügen, Vergießen und Beschichten unter Verwendung der Masse |
| CN113518805B (zh) | 2018-12-28 | 2023-08-08 | 意大利艾坚蒙树脂有限公司 | 光引发剂 |
| WO2021070152A1 (en) | 2019-10-11 | 2021-04-15 | Igm Resins Italia S.R.L. | Coumarin glyoxylates for led photocuring |
| IT202000023815A1 (it) | 2020-10-09 | 2022-04-09 | Igm Resins Italia Srl | Ketoquinolones as photonitiators |
| IT202100014885A1 (it) | 2021-06-08 | 2022-12-08 | Igm Resins Italia Srl | Fotoiniziatori a base di silicio bifunzionali |
| IT202100025868A1 (it) | 2021-10-08 | 2023-04-08 | Igm Resins Italia Srl | Nuovi fotoiniziatori |
| WO2023161049A1 (en) | 2022-02-24 | 2023-08-31 | Igm Resins Italia S.R.L. | Photoinitiators |
| DE102022106647A1 (de) | 2022-03-22 | 2023-09-28 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Niedertemperaturhärtende Massen auf Basis von Glycidylethern |
| CN119137224A (zh) | 2022-05-06 | 2024-12-13 | Igm集团公司 | 包含氧化膦光引发剂、基于香豆素的敏化剂和胺添加剂的光引发剂包 |
| EP4519377A1 (en) | 2022-05-06 | 2025-03-12 | IGM Group B.V. | Photoinitiator package comprising phosphine oxide photoinitiators, oxazole-based sensitizers and amine additives |
| EP4273200A1 (en) | 2022-05-06 | 2023-11-08 | IGM Group B.V. | Photoinitiator package comprising specialised bisacylphosphine oxide photoinitiators and optical brightener sensitizers |
| EP4598967A1 (en) | 2022-10-05 | 2025-08-13 | IGM Resins Italia S.r.l. | Polymeric (meth)acrylate photoinitiators |
| IT202300004737A1 (it) | 2023-03-14 | 2024-09-14 | Igm Resins Italia Srl | Uso di fotoiniziatori specifici in un processo di fotopolimerizzazione utilizzando lunghezze d’onda combinate di luce a led |
| WO2025027517A1 (en) | 2023-08-03 | 2025-02-06 | Igm Resins Italia S.R.L. | 10,11 -dihydro-5h-dibenzo[b,f]azepine derivatives as photoinitiatiors in photopolymerisation for use in photocurable compositions |
| EP4534614A1 (en) | 2023-10-02 | 2025-04-09 | IGM Group B.V. | Photoinitiator package comprising specialised bisacylphosphine oxide photoinitiators, further acylphosphine oxide photoinitiators and optical brightener sensitizers |
| WO2025140854A2 (en) | 2023-12-28 | 2025-07-03 | Igm Resins Italia S.R.L. | NOVEL SOLID FORM OF BIS(2,4,6-TRIMETHYLBENZOYL)-n-OCTYL-PHOSPHINE OXIDE |
| EP4579344A1 (en) | 2023-12-29 | 2025-07-02 | IGM Group B.V. | Thioalkylcoumarin photosensitizers for photopolymerization |
| EP4578918A1 (en) | 2023-12-29 | 2025-07-02 | IGM Group B.V. | Photosensitizers for photopolymerization |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4540598A (en) | 1983-08-17 | 1985-09-10 | Ciba-Geigy Corporation | Process for curing acid-curable finishes |
| JPH04362647A (ja) * | 1991-06-10 | 1992-12-15 | Konica Corp | 感光性組成物 |
| DE59309494D1 (de) | 1992-05-22 | 1999-05-12 | Ciba Geigy Ag | Hochauflösender I-Linien Photoresist mit höherer Empfindlichkeit |
| JPH0990627A (ja) * | 1995-09-27 | 1997-04-04 | Toray Ind Inc | 感光性ポリイミド前駆体組成物 |
| JP3830183B2 (ja) * | 1995-09-29 | 2006-10-04 | 東京応化工業株式会社 | オキシムスルホネート化合物及びレジスト用酸発生剤 |
| MY117352A (en) | 1995-10-31 | 2004-06-30 | Ciba Sc Holding Ag | Oximesulfonic acid esters and the use thereof as latent sulfonic acids. |
| JP3591743B2 (ja) * | 1996-02-02 | 2004-11-24 | 東京応化工業株式会社 | 化学増幅型レジスト組成物 |
| DE69721019T2 (de) | 1996-09-02 | 2003-12-24 | Ciba Speciality Chemicals Holding Inc., Basel | Alkylsulfonyloxime für i-line-photoresists hoher auflösung und empfindlichkeit |
| JP3655030B2 (ja) | 1996-12-10 | 2005-06-02 | 東京応化工業株式会社 | ネガ型化学増幅型レジスト組成物 |
| TW550439B (en) * | 1997-07-01 | 2003-09-01 | Ciba Sc Holding Ag | New oxime sulfonates as latent acids and compositions and photoresists comprising said oxime sulfonates |
| EP1124832B1 (en) * | 1998-10-29 | 2002-11-20 | Ciba SC Holding AG | Oxime derivatives and the use thereof as latent acids |
| EP1192106B1 (en) * | 1999-03-05 | 2003-06-11 | ExxonMobil Research and Engineering Company | Rare earth metal ion exchanged ferrierite |
-
1999
- 1999-10-18 EP EP99950753A patent/EP1124832B1/en not_active Expired - Lifetime
- 1999-10-18 JP JP2000579607A patent/JP2002528550A/ja not_active Ceased
- 1999-10-18 KR KR1020017005334A patent/KR100634037B1/ko not_active Expired - Fee Related
- 1999-10-18 DE DE69904073T patent/DE69904073T2/de not_active Expired - Lifetime
- 1999-10-18 AU AU63408/99A patent/AU6340899A/en not_active Abandoned
- 1999-10-18 CN CNA2004100925757A patent/CN1636971A/zh active Pending
- 1999-10-18 CN CNB99812849XA patent/CN1205215C/zh not_active Expired - Fee Related
- 1999-10-18 WO PCT/EP1999/007876 patent/WO2000026219A1/en not_active Ceased
- 1999-10-18 US US09/830,248 patent/US6485886B1/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN120737322A (zh) * | 2025-09-02 | 2025-10-03 | 西北工业大学 | 一种基于手性主链的液晶聚合物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1325401A (zh) | 2001-12-05 |
| AU6340899A (en) | 2000-05-22 |
| EP1124832B1 (en) | 2002-11-20 |
| EP1124832A1 (en) | 2001-08-22 |
| WO2000026219A1 (en) | 2000-05-11 |
| DE69904073T2 (de) | 2003-07-17 |
| DE69904073D1 (de) | 2003-01-02 |
| KR20010081100A (ko) | 2001-08-27 |
| KR100634037B1 (ko) | 2006-10-17 |
| JP2002528550A (ja) | 2002-09-03 |
| CN1205215C (zh) | 2005-06-08 |
| US6485886B1 (en) | 2002-11-26 |
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