CN1636971A - 肟衍生物及其作为潜酸的用途 - Google Patents

Info

Publication number

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

Authority

CN

China

Prior art keywords

acid

phenyl

substituted

alkyl

compounds

Prior art date

1998-10-29

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.)

Pending

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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
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• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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