TWI351396B - Halogenated oxime derivatives and the use thereof - Google Patents
Halogenated oxime derivatives and the use thereof Download PDFInfo
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- TWI351396B TWI351396B TW93103971A TW93103971A TWI351396B TW I351396 B TWI351396 B TW I351396B TW 93103971 A TW93103971 A TW 93103971A TW 93103971 A TW93103971 A TW 93103971A TW I351396 B TWI351396 B TW I351396B
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- Prior art keywords
- acid
- compound
- phenyl
- group
- formula
- Prior art date
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- 150000002923 oximes Chemical class 0.000 title claims description 4
- -1 biphenylyl Chemical group 0.000 claims description 134
- 239000002253 acid Substances 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000003112 inhibitor Substances 0.000 claims description 21
- 238000000576 coating method Methods 0.000 claims description 20
- 229920002120 photoresistant polymer Polymers 0.000 claims description 19
- 239000011248 coating agent Substances 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- 230000007797 corrosion Effects 0.000 claims description 13
- 238000005260 corrosion Methods 0.000 claims description 13
- 239000004305 biphenyl Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 238000004132 cross linking Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000011161 development Methods 0.000 claims description 7
- 230000018109 developmental process Effects 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 3
- 238000003709 image segmentation Methods 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 230000036211 photosensitivity Effects 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 101100241454 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nuc-2 gene Proteins 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 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 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 48
- 229920000642 polymer Polymers 0.000 description 36
- 238000009472 formulation Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 12
- 239000011976 maleic acid Substances 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 229960003742 phenol Drugs 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000012964 benzotriazole Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 10
- 238000004293 19F NMR spectroscopy Methods 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000010894 electron beam technology Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- 239000003504 photosensitizing agent Substances 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000234282 Allium Species 0.000 description 7
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000002466 imines Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 230000003321 amplification Effects 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 229920001038 ethylene copolymer Polymers 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 238000003199 nucleic acid amplification method Methods 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 238000003971 tillage Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 3
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241000220317 Rosa Species 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 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
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 2
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 2
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical group NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- MBGGFXOXUIDRJD-UHFFFAOYSA-N 4-Butoxyphenol Chemical compound CCCCOC1=CC=C(O)C=C1 MBGGFXOXUIDRJD-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 241000208140 Acer Species 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
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- 150000004678 hydrides Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl 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])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
- 238000003860 storage Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BGKZULDOBMANRY-UHFFFAOYSA-N sulfanyl prop-2-enoate Chemical compound SOC(=O)C=C BGKZULDOBMANRY-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002345 surface coating layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- ZYSDERHSJJEJDS-UHFFFAOYSA-M tetrakis-decylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[N+](CCCCCCCCCC)(CCCCCCCCCC)CCCCCCCCCC ZYSDERHSJJEJDS-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- IROUUJMLXUIGMV-UHFFFAOYSA-N trifluoromethyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(F)(F)F IROUUJMLXUIGMV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/20—Acenaphthenes; Hydrogenated acenaphthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials For Photolithography (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03405103 | 2003-02-19 | ||
| EP03405130 | 2003-02-27 | ||
| EP03405432 | 2003-06-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200428147A TW200428147A (en) | 2004-12-16 |
| TWI351396B true TWI351396B (en) | 2011-11-01 |
Family
ID=32912624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW93103971A TWI351396B (en) | 2003-02-19 | 2004-02-18 | Halogenated oxime derivatives and the use thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7399577B2 (enExample) |
| EP (1) | EP1595182B1 (enExample) |
| JP (1) | JP4560507B2 (enExample) |
| KR (1) | KR101043905B1 (enExample) |
| CN (1) | CN105541659A (enExample) |
| BR (1) | BRPI0407605A (enExample) |
| CA (1) | CA2511979A1 (enExample) |
| MX (1) | MXPA05008118A (enExample) |
| TW (1) | TWI351396B (enExample) |
| WO (1) | WO2004074242A2 (enExample) |
Families Citing this family (283)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI272451B (en) * | 2000-09-25 | 2007-02-01 | Ciba Sc Holding Ag | Chemically amplified photoresist composition, process for preparation of a photoresist, and use of said chemically amplified photoresist composition |
| WO2006008250A2 (en) * | 2004-07-20 | 2006-01-26 | Ciba Specialty Chemicals Holding Inc. | Oxime derivatives and the use therof as latent acids |
| US7459261B2 (en) | 2005-01-06 | 2008-12-02 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process using the same |
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| US7387969B2 (en) * | 2005-03-18 | 2008-06-17 | Taiwan Semiconductor Manufacturing Co., Ltd. | Top patterned hardmask and method for patterning |
| TWI332122B (en) | 2005-04-06 | 2010-10-21 | Shinetsu Chemical Co | Novel sulfonate salts and derivatives, photoacid generators, resist compositions and patterning process |
| JP4732046B2 (ja) | 2005-07-20 | 2011-07-27 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
| JP4762630B2 (ja) | 2005-08-03 | 2011-08-31 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
| JP4536622B2 (ja) | 2005-08-23 | 2010-09-01 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
| JP4979915B2 (ja) | 2005-09-09 | 2012-07-18 | 東京応化工業株式会社 | 高分子化合物、ネガ型レジスト組成物およびレジストパターン形成方法 |
| WO2007034719A1 (ja) | 2005-09-20 | 2007-03-29 | Tokyo Ohka Kogyo Co., Ltd. | 化合物およびその製造方法、ポジ型レジスト組成物およびレジストパターン形成方法 |
| JP4574507B2 (ja) * | 2005-09-28 | 2010-11-04 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
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| EP1780198B1 (en) | 2005-10-31 | 2011-10-05 | Shin-Etsu Chemical Co., Ltd. | Novel fluorosulfonyloxyalkyl sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process |
| EP1780199B1 (en) | 2005-10-31 | 2012-02-01 | Shin-Etsu Chemical Co., Ltd. | Novel fluorohydroxyalkyl sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process |
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| JP7495897B2 (ja) | 2021-03-23 | 2024-06-05 | 信越化学工業株式会社 | ポジ型感光性樹脂組成物、ポジ型感光性ドライフィルム、ポジ型感光性ドライフィルムの製造方法、パターン形成方法、硬化被膜形成方法、層間絶縁膜、表面保護膜、及び電子部品 |
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|---|---|---|---|---|
| US4566901A (en) * | 1982-05-06 | 1986-01-28 | Ciba-Geigy Corporation | Novel oxime ethers, the preparation thereof, compositions containing them and the use thereof |
| US4540598A (en) | 1983-08-17 | 1985-09-10 | Ciba-Geigy Corporation | Process for curing acid-curable finishes |
| DE3660255D1 (en) | 1985-04-12 | 1988-07-07 | Ciba Geigy Ag | Oxime sulphonates containing reactive groups |
| DE59309494D1 (de) | 1992-05-22 | 1999-05-12 | Ciba Geigy Ag | Hochauflösender I-Linien Photoresist mit höherer Empfindlichkeit |
| 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. |
| US20010037037A1 (en) * | 1995-10-31 | 2001-11-01 | Kurt Dietliker | Oximesulfonic acid esters and the use thereof as latent sulfonic acids |
| JP3879139B2 (ja) * | 1996-05-08 | 2007-02-07 | 住友化学株式会社 | グリオキシム系エステル、その製法および用途 |
| AU734489B2 (en) * | 1997-06-03 | 2001-06-14 | Novartis Ag | Fluoroalkenecarboxylic acid derivatives, processes for their preparation and insecticidal compositions comprising them |
| TW575792B (en) * | 1998-08-19 | 2004-02-11 | Ciba Sc Holding Ag | New unsaturated oxime derivatives and the use thereof as latent acids |
| WO2000052530A1 (en) * | 1999-03-03 | 2000-09-08 | Ciba Specialty Chemicals Holding Inc. | Oxime derivatives and the use thereof as photoinitiators |
| SG78412A1 (en) * | 1999-03-31 | 2001-02-20 | 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. |
| TWI272451B (en) | 2000-09-25 | 2007-02-01 | Ciba Sc Holding Ag | Chemically amplified photoresist composition, process for preparation of a photoresist, and use of said chemically amplified photoresist composition |
| JP4225699B2 (ja) * | 2001-03-12 | 2009-02-18 | 富士フイルム株式会社 | ポジ型感光性組成物 |
| JP4210439B2 (ja) * | 2001-04-05 | 2009-01-21 | 富士フイルム株式会社 | ポジ型フォトレジスト組成物 |
| ATE288907T1 (de) | 2001-06-01 | 2005-02-15 | Ciba Sc Holding Ag | Substituierte oxim-derivate und ihre verwendung als latente säuren |
| WO2002100903A1 (en) * | 2001-06-11 | 2002-12-19 | Ciba Specialty Chemicals Holding Inc. | Oxime ester photoinitiators having a combined structure |
| CA2474532A1 (en) | 2002-02-06 | 2003-08-14 | Peter Murer | Sulfonate derivatives and the use therof as latent acids |
| JP2003307838A (ja) * | 2002-04-15 | 2003-10-31 | Fuji Photo Film Co Ltd | ポジ型感光性組成物 |
| WO2006008250A2 (en) * | 2004-07-20 | 2006-01-26 | Ciba Specialty Chemicals Holding Inc. | Oxime derivatives and the use therof as latent acids |
-
2004
- 2004-02-09 MX MXPA05008118A patent/MXPA05008118A/es unknown
- 2004-02-09 JP JP2006502011A patent/JP4560507B2/ja not_active Expired - Fee Related
- 2004-02-09 CN CN201510923408.0A patent/CN105541659A/zh active Pending
- 2004-02-09 EP EP04709242.4A patent/EP1595182B1/en not_active Expired - Lifetime
- 2004-02-09 BR BRPI0407605-2A patent/BRPI0407605A/pt not_active Application Discontinuation
- 2004-02-09 WO PCT/EP2004/050096 patent/WO2004074242A2/en not_active Ceased
- 2004-02-09 KR KR20057015430A patent/KR101043905B1/ko not_active Expired - Fee Related
- 2004-02-09 US US10/543,429 patent/US7399577B2/en not_active Expired - Lifetime
- 2004-02-09 CA CA002511979A patent/CA2511979A1/en not_active Abandoned
- 2004-02-18 TW TW93103971A patent/TWI351396B/zh not_active IP Right Cessation
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2008
- 2008-05-22 US US12/154,333 patent/US8241822B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TW200428147A (en) | 2004-12-16 |
| US20060246377A1 (en) | 2006-11-02 |
| MXPA05008118A (es) | 2005-09-30 |
| WO2004074242A3 (en) | 2005-02-03 |
| EP1595182A2 (en) | 2005-11-16 |
| JP4560507B2 (ja) | 2010-10-13 |
| CA2511979A1 (en) | 2004-09-02 |
| EP1595182B1 (en) | 2015-09-30 |
| JP2006517950A (ja) | 2006-08-03 |
| WO2004074242A2 (en) | 2004-09-02 |
| US20090042114A1 (en) | 2009-02-12 |
| KR20050115863A (ko) | 2005-12-08 |
| BRPI0407605A (pt) | 2006-02-14 |
| CN105541659A (zh) | 2016-05-04 |
| KR101043905B1 (ko) | 2011-06-29 |
| US8241822B2 (en) | 2012-08-14 |
| US7399577B2 (en) | 2008-07-15 |
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