JP2002528550A - オキシム誘導体及び潜在性酸としてのその使用 - Google Patents
オキシム誘導体及び潜在性酸としてのその使用Info
- Publication number
- JP2002528550A JP2002528550A JP2000579607A JP2000579607A JP2002528550A JP 2002528550 A JP2002528550 A JP 2002528550A JP 2000579607 A JP2000579607 A JP 2000579607A JP 2000579607 A JP2000579607 A JP 2000579607A JP 2002528550 A JP2002528550 A JP 2002528550A
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- compound
- substituted
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000002253 acid Substances 0.000 title claims abstract description 74
- 150000007513 acids Chemical class 0.000 title claims abstract description 13
- 150000002923 oximes Chemical class 0.000 title description 39
- -1 anthracyl Chemical group 0.000 claims abstract description 138
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 69
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 11
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000006331 halo benzoyl group Chemical group 0.000 claims abstract description 7
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 93
- 238000000576 coating method Methods 0.000 claims description 44
- 239000011248 coating agent Substances 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 20
- 238000004132 cross linking Methods 0.000 claims description 17
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 15
- 238000007639 printing Methods 0.000 claims description 14
- 230000009471 action Effects 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 238000011161 development Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 10
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 230000001678 irradiating effect Effects 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 6
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 49
- 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 42
- 239000007787 solid Substances 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000005855 radiation Effects 0.000 description 20
- 239000011230 binding agent Substances 0.000 description 16
- 238000001723 curing Methods 0.000 description 16
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229920000877 Melamine resin Polymers 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 229920001225 polyester resin Polymers 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 239000004922 lacquer Substances 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- CEQPEKHLBZNDQM-UHFFFAOYSA-N 2-(4-hydroxyiminocyclohexa-2,5-dien-1-ylidene)-2-phenylacetonitrile Chemical compound C1=CC(=NO)C=CC1=C(C#N)C1=CC=CC=C1 CEQPEKHLBZNDQM-UHFFFAOYSA-N 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- 229920003180 amino resin Polymers 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
- 239000000460 chlorine Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 238000007171 acid catalysis Methods 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical class OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- 239000004642 Polyimide Substances 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 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
- 239000002585 base Substances 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
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- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- ZYCFSHNWYDMFPB-UHFFFAOYSA-N 2-phenyl-2-(4-triphenylsilyloxyiminocyclohexa-2,5-dien-1-ylidene)acetonitrile Chemical compound C=1C=CC=CC=1C(C#N)=C(C=C1)C=CC1=NO[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZYCFSHNWYDMFPB-UHFFFAOYSA-N 0.000 description 2
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- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSHQRDRGVZKEQP-UHFFFAOYSA-N tert-butyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(C)(C)OC(=O)C=C JSHQRDRGVZKEQP-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
- 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
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 230000007704 transition Effects 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-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
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98811084.7 | 1998-10-29 | ||
| EP98811084 | 1998-10-29 | ||
| PCT/EP1999/007876 WO2000026219A1 (en) | 1998-10-29 | 1999-10-18 | Oxime derivatives and the use thereof as latent acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002528550A true JP2002528550A (ja) | 2002-09-03 |
| JP2002528550A5 JP2002528550A5 (enExample) | 2006-11-30 |
Family
ID=8236416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000579607A Ceased JP2002528550A (ja) | 1998-10-29 | 1999-10-18 | オキシム誘導体及び潜在性酸としてのその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6485886B1 (enExample) |
| EP (1) | EP1124832B1 (enExample) |
| JP (1) | JP2002528550A (enExample) |
| KR (1) | KR100634037B1 (enExample) |
| CN (2) | CN1205215C (enExample) |
| AU (1) | AU6340899A (enExample) |
| DE (1) | DE69904073T2 (enExample) |
| WO (1) | WO2000026219A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100634037B1 (ko) * | 1998-10-29 | 2006-10-17 | 시바 스페셜티 케미칼스 홀딩 인크. | 옥심 유도체, 이의 제조방법 및 이를 포함하는 조성물 |
| NL1014545C2 (nl) * | 1999-03-31 | 2002-02-26 | Ciba Sc Holding Ag | Oxim-derivaten en de toepassing daarvan als latente zuren. |
| DK1392675T3 (da) * | 2001-06-01 | 2005-04-04 | Ciba Sc Holding Ag | Substituerede oximderivater og anvendelsen deraf som latente syrer |
| US7098463B2 (en) * | 2003-03-03 | 2006-08-29 | Heuris Pharma, Llc | Three-dimensional dosimeter for penetrating radiation and method of use |
| KR20060002751A (ko) * | 2003-03-11 | 2006-01-09 | 후지필름 일렉트로닉 머티리얼스 유.에스.에이., 아이엔씨. | 새로운 감광성 수지 조성물들 |
| US20070020793A1 (en) * | 2004-03-01 | 2007-01-25 | Adamovics John A | Three-dimensional shaped solid dosimeter and method of use |
| 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 |
| US20120043480A1 (en) | 2009-03-30 | 2012-02-23 | Basf Se | Uv-dose indicator films |
| JP5996430B2 (ja) * | 2009-09-18 | 2016-09-21 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | ホスホネート接合組成物 |
| 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 |
| US9145383B2 (en) | 2012-08-10 | 2015-09-29 | Hallstar Innovations Corp. | Compositions, apparatus, systems, and methods for resolving electronic excited states |
| US9867800B2 (en) | 2012-08-10 | 2018-01-16 | Hallstar Innovations Corp. | Method of quenching singlet and triplet excited states of pigments, such as porphyrin compounds, particularly protoporphyrin IX, with conjugated fused tricyclic compounds have electron withdrawing groups, to reduce generation of reactive oxygen species, particularly singlet oxygen |
| EP3149013B1 (en) | 2014-05-30 | 2018-10-24 | IGM Resins Italia S.r.l. | Multifunctional acylphosphine oxide photoinitiators |
| JP6812361B2 (ja) | 2015-04-29 | 2021-01-13 | ビーエスエヌ メディカル ゲーエムベーハー | 医療用入浴機器 |
| AU2016256186B2 (en) | 2015-04-29 | 2020-01-16 | Bsn Medical Gmbh | Multi-step process for no production |
| 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 |
| CN110325912B (zh) * | 2017-02-23 | 2023-07-14 | 艾曲迪微系统股份有限公司 | 感光性树脂组合物、图案的制造方法、固化物、层间绝缘膜、覆盖涂层、保护膜和电子部件 |
| 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 |
| CN112673012B (zh) | 2018-09-07 | 2024-05-24 | 意大利艾坚蒙树脂有限公司 | 多官能双酰基氧化膦光引发剂 |
| 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 |
| EP4273200A1 (en) | 2022-05-06 | 2023-11-08 | IGM Group B.V. | Photoinitiator package comprising specialised bisacylphosphine oxide photoinitiators and optical brightener sensitizers |
| US20250304727A1 (en) | 2022-05-06 | 2025-10-02 | Igm Group B. V. | Photoinitiator package comprising phosphine oxide photoinitiators, coumarin-based sensitizers and amine additives |
| EP4519377A1 (en) | 2022-05-06 | 2025-03-12 | IGM Group B.V. | Photoinitiator package comprising phosphine oxide photoinitiators, oxazole-based sensitizers and amine additives |
| 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 |
| CN120737322B (zh) * | 2025-09-02 | 2025-11-28 | 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2002508774A (ja) * | 1997-07-01 | 2002-03-19 | 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 | 新規なオキシムスルホナート類及び潜伏性スルホン酸としてのこれらの用途 |
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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 |
| EP0571330B1 (de) | 1992-05-22 | 1999-04-07 | Ciba SC Holding 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 |
| CA2263254A1 (en) | 1996-09-02 | 1998-03-12 | Ciba Specialty Chemicals Holding Inc. | Alkysulfonyloximes for high-resolution i-line photoresists of high sensitivity |
| 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 |
| KR100634037B1 (ko) * | 1998-10-29 | 2006-10-17 | 시바 스페셜티 케미칼스 홀딩 인크. | 옥심 유도체, 이의 제조방법 및 이를 포함하는 조성물 |
| WO2000053530A1 (en) * | 1999-03-05 | 2000-09-14 | Exxon Research And Engineering Company | Rare earth metal ion exchanged ferrierite |
-
1999
- 1999-10-18 KR KR1020017005334A patent/KR100634037B1/ko not_active Expired - Fee Related
- 1999-10-18 AU AU63408/99A patent/AU6340899A/en not_active Abandoned
- 1999-10-18 JP JP2000579607A patent/JP2002528550A/ja not_active Ceased
- 1999-10-18 EP EP99950753A patent/EP1124832B1/en not_active Expired - Lifetime
- 1999-10-18 WO PCT/EP1999/007876 patent/WO2000026219A1/en not_active Ceased
- 1999-10-18 DE DE69904073T patent/DE69904073T2/de not_active Expired - Lifetime
- 1999-10-18 US US09/830,248 patent/US6485886B1/en not_active Expired - Fee Related
- 1999-10-18 CN CNB99812849XA patent/CN1205215C/zh not_active Expired - Fee Related
- 1999-10-18 CN CNA2004100925757A patent/CN1636971A/zh active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002508774A (ja) * | 1997-07-01 | 2002-03-19 | 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 | 新規なオキシムスルホナート類及び潜伏性スルホン酸としてのこれらの用途 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69904073T2 (de) | 2003-07-17 |
| CN1205215C (zh) | 2005-06-08 |
| AU6340899A (en) | 2000-05-22 |
| CN1636971A (zh) | 2005-07-13 |
| WO2000026219A1 (en) | 2000-05-11 |
| CN1325401A (zh) | 2001-12-05 |
| KR100634037B1 (ko) | 2006-10-17 |
| DE69904073D1 (de) | 2003-01-02 |
| KR20010081100A (ko) | 2001-08-27 |
| EP1124832B1 (en) | 2002-11-20 |
| EP1124832A1 (en) | 2001-08-22 |
| US6485886B1 (en) | 2002-11-26 |
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