CN101528682A - 肟酯化合物和含有该化合物的光聚合引发剂 - Google Patents
肟酯化合物和含有该化合物的光聚合引发剂 Download PDFInfo
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- CN101528682A CN101528682A CNA2007800403335A CN200780040333A CN101528682A CN 101528682 A CN101528682 A CN 101528682A CN A2007800403335 A CNA2007800403335 A CN A2007800403335A CN 200780040333 A CN200780040333 A CN 200780040333A CN 101528682 A CN101528682 A CN 101528682A
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- Prior art keywords
- compound
- methyl
- carbonatoms
- acid
- alkyl
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- -1 Oxime ester compound Chemical class 0.000 title claims abstract description 132
- 150000001875 compounds Chemical class 0.000 title claims description 85
- 239000003999 initiator Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 239000002131 composite material Substances 0.000 claims description 54
- 229920005989 resin Polymers 0.000 claims description 43
- 239000011347 resin Substances 0.000 claims description 43
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000003086 colorant Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 239000004593 Epoxy Substances 0.000 description 38
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000035945 sensitivity Effects 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 150000007518 monoprotic acids Chemical class 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 235000013824 polyphenols Nutrition 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 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 6
- 229940043232 butyl acetate Drugs 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical class CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- 239000006229 carbon black Substances 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229940049920 malate Drugs 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical class CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 229940042596 viscoat Drugs 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- NQBWNECTZUOWID-UHFFFAOYSA-N (E)-cinnamyl (E)-cinnamate Natural products C=1C=CC=CC=1C=CC(=O)OCC=CC1=CC=CC=C1 NQBWNECTZUOWID-UHFFFAOYSA-N 0.000 description 2
- 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
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
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- JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-UHFFFAOYSA-N 0.000 description 2
- IQCASZIDTNHBIW-UHFFFAOYSA-N 2-(pentoxymethyl)oxirane Chemical compound CCCCCOCC1CO1 IQCASZIDTNHBIW-UHFFFAOYSA-N 0.000 description 2
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 2
- UGFIPXHCRZOKEF-UHFFFAOYSA-N 2-benzofuran-1,3-dione;furan-2,5-dione Chemical compound O=C1OC(=O)C=C1.C1=CC=C2C(=O)OC(=O)C2=C1 UGFIPXHCRZOKEF-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
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- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/63—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
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- 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
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- C07D209/82—Carbazoles; Hydrogenated carbazoles
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Abstract
一种由右述通式(I)表示的肟酯化合物,式中,R1和R2分别独立地表示R11、OR11、COR11、SR11、CONR12R13或CN,R11、R12和R13分别独立地表示氢原子、碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳烷基或碳原子数为2~20的杂环基,R3和R4分别独立地表示R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11、CN、卤原子或羟基,a和b分别独立地为0~4;X表示氧原子、硫原子、硒原子、CR31R32、CO、NR33或PR34,R31、R32、R33和R34分别独立地表示R11、OR11、COR11、SR11、CONR12R13或CN。
Description
技术领域
本发明涉及作为感光性组合物中使用的光聚合引发剂而有用的新型肟酯化合物、以该化合物作为有效成分的光聚合引发剂、以及在具有烯键式不饱和键的聚合性化合物中含有该光聚合引发剂而形成的感光性组合物。
背景技术
感光性组合物是在具有烯键式不饱和键的聚合性化合物中加入光聚合引发剂而得到的,通过对该感光性组合物照射405nm或365nm的光,可以使其聚合固化,因而可用于光固化性油墨、感光性印刷版、各种光致抗蚀剂等。
作为用于上述感光性组合物的光聚合引发剂,在下述专利文献1~8中提出了使用具有咔唑基结构的O-酰基肟化合物的技术。但是这些公知的O-酰基肟化合物在特别是灵敏度方面还不能充分满足。
专利文献1:日本特开2001-302871号说明书
专利文献2:日本特表2004-534797号说明书
专利文献3:日本特开2005-25169号说明书
专利文献4:日本特开2005-128483号说明书
专利文献5:日本特开2005-242279号说明书
专利文献6:日本特开2005-242280号说明书
专利文献7:日本特开2006-16545号说明书
专利文献8:日本特许3754065号说明书
发明内容
本发明要解决的问题是到目前为止还没有具有能够满足的灵敏度的光聚合引发剂。
因此,本发明的目的是提供一种能高效地吸收405nm或365nm等长波长的光而活化的高灵敏度的光聚合引发剂。
本发明通过提供下述通式(I)表示的肟酯化合物和以该化合物作为有效成分的光聚合引发剂,实现了上述目的。
(式中,R1和R2分别独立地表示R11、OR11、COR11、SR11、CONR12R13或CN,R11、R12和R13分别独立地表示氢原子、碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳烷基或碳原子数为2~20的杂环基,烷基、芳基、芳烷基和杂环基的氢原子进而还可以被OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、CN、卤原子、-CR21=CR22R23、-CO-CR21=CR22R23、羧基、环氧基取代,R21、R22和R23分别独立地表示氢原子、碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳烷基或碳原子数为2~20的杂环基,上述R11、R12、R13、R21、R22和R23表示的取代基的亚烷基部分的亚甲基也可以被不饱和键、醚键、硫醚键、酯键、硫酯键、酰胺键或氨基甲酸酯键中断1~5次,上述取代基的烷基部分可以具有分支侧链,也可以是环状烷基,上述取代基的烷基末端也可以是不饱和键,而且,R12和R13、以及R22和R23也可以分别一起形成环,R3和R4分别独立地表示R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11、CN、卤原子或羟基,a和b分别独立地为0~4,X表示氧原子、硫原子、硒原子、CR31R32、CO、NR33或PR34,R31、R32、R33和R34分别独立地表示R11、OR11、COR11、SR11、CONR12R13或CN,R3也可以通过-X-与邻接的苯环的一个碳原子结合而形成环结构,或者R3和R4也可以一起形成环,R31、R33和R34也可以分别独立地与邻接的任何一个苯环一起形成环。)
另外,本发明提供一种感光性组合物,其含有上述光聚合引发剂和具有烯键式不饱和键的聚合性化合物。
另外,本发明提供一种碱显影性感光性树脂组合物,其含有上述光聚合引发剂和具有烯键式不饱和键的碱显影性化合物。
另外,本发明提供一种着色碱显影性感光性树脂组合物,其是在上述碱显影性感光性树脂组合物中进一步含有色料而形成的。
具体实施方式
下面,对本发明的肟酯化合物和以该化合物作为有效成分的光聚合引发剂进行详细说明。
上述通式(I)中,作为R11、R12、R13、R21、R22、R23、R31、R32、R33和R34表示的烷基,可以列举出例如甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、叔戊基、己基、庚基、辛基、异辛基、2-乙基己基、叔辛基、壬基、异壬基、癸基、异癸基、十一烷基、十二烷基、环戊基、环己基、乙烯基、烯丙基、丁烯基、乙炔基、丙炔基、甲氧基乙基、乙氧基乙基、丙氧基乙基、戊氧基乙基、辛氧基乙基、甲氧基乙氧基乙基、乙氧基乙氧基乙基、丙氧基乙氧基乙基、甲氧基丙基、2-(苯并噁唑-2’-基)乙烯基等,其中优选碳原子数为3~8的烷基。作为R11、R12、R13、R21、R22、R23、R31、R32、R33和R34表示的芳基,可以列举出例如苯基、甲苯基、二甲苯基、乙基苯基、氯苯基、萘基、蒽基、菲基等,其中优选碳原子数为6~12的芳基。作为R11、R12、R13、R21、R22、R23、R31、R32、R33和R34表示的芳烷基,可以优选列举出例如苄基、氯苄基、α-甲基苄基、α,α-二甲基苄基、苯基乙基、苯基乙烯基等碳原子数为7~13的芳烷基。作为R11、R12、R13、R21、R22、R23、R31、R32、R33和R34表示的杂环基,可以优选列举出例如吡啶基、嘧啶基、呋喃基、噻嗯基、四氢呋喃基、二氧杂环戊基等5~7元杂环。此外,作为R12和R13可以一起形成的环、R22和R23可以一起形成的环、R3和R4可以一起形成的环、R3可以通过-X-与邻接的苯环的一个碳原子结合而形成的环结构、以及R31、R33、R34可以与邻接的苯环一起形成的环,可以优选列举出例如环戊烷环、环己烷环、环戊烯环、苯环、哌啶环、吗啉环、内酯环、内酰胺环等5~7元环。
另外,作为可以取代R11、R12、R13、R21、R22、R23、R31、R32、R33和R34的卤原子,可以列举出氟、氯、溴、碘。作为可以取代R11、R12、R13、R21、R22、R23、R31、R32、R33和R34的杂环基,可以列举出例如吡啶基、嘧啶基、呋喃基、苯并噁唑-2-基、四氢吡喃基、吡咯烷基、咪唑烷基、吡唑烷基、噻唑烷基、异噻唑烷基、噁唑烷基、异噁唑烷基、哌啶基、哌嗪基、吗啉基等5~7元杂环基。另外,作为R3和R4表示的卤原子,可以列举出氟、氯、溴、碘。
上述取代基的亚烷基部分的亚甲基也可以被不饱和键、醚键、硫醚键、酯键、硫酯键、酰胺键或氨基甲酸酯键中断1~5次,此时中断的连结基团(linking group)也可以是1种或2种以上的基团,在为能够连续中断的基团的情况下,也可以2个以上的连结基团连续地中断。另外,上述取代基的烷基部分可以具有分支侧链,也可以是环状烷基,上述取代基的烷基末端也可以是不饱和键。
本发明的肟酯化合物中,优选的是,上述通式(I)中,R1是可以被卤原子取代的碳原子数为6~30的芳基、特别是苯基的肟酯化合物;R2是也可以为环状烷基、也可以被卤原子取代的碳原子数为1~20的烷基、特别是甲基的肟酯化合物;X是硫原子或NR33,并且R33是可以具有分支侧链、可以为环状烷基、且可以被卤原子取代的碳原子数为1~20的烷基、特别是辛基的肟酯化合物;由于这些肟酯化合物容易合成且灵敏度也高,所以是优选的。
本发明的肟酯化合物还可以如下述[化学式2]所示那样,通过R1而二聚化。
[化学式2]
因此,作为上述通式(I)表示的本发明的肟酯化合物的优选的具体例子,可以列举出以下的化合物No.1~No.24的化合物。但是,本发明不受以下化合物的任何限制。
上述通式(I)表示的本发明的肟酯化合物的合成方法没有特别限定,例如X是硫原子的肟酯化合物可以按照下述[化学式27]的反应式通过以下的方法来制备。首先,在氢氧化钠的存在下使对氯硝基苯1和苯硫酚2反应,得到硫化物3,然后,在氯化铝的存在下使硫化物3和酰氯4反应,得到酰基化合物5。接着,使酰基化合物5和亚硝酸烷基酯6,然后和酸酐7或酰氯7’反应,得到上述通式(I)中的X是硫原子的本发明的肟酯化合物。而且,X是氧原子、硒原子、CR33R34、N-R33或P-R34的肟酯化合物也可以按照上述方法来制造。
[化学式27]
本发明的肟酯化合物作为具有烯键式不饱和键的聚合性化合物的光聚合引发剂是有用的。
下面,对本发明的感光性组合物进行说明。
本发明的感光性组合物含有以上述的本发明的肟酯化合物作为有效成分的光聚合引发剂及具有烯键式不饱和键的聚合性化合物、以及根据需要添加的无机填充剂和/或色料、还有溶剂等任意成分。
作为上述具有烯键式不饱和键的聚合性化合物,没有特别限定,可以使用以往用于感光性组合物的化合物,可以列举出例如乙烯、丙烯、丁烯、异丁烯、氯乙烯、偏氯乙烯、偏氟乙烯、四氟乙烯等不饱和脂肪族烃;(甲基)丙烯酸、α-氯代丙烯酸、衣康酸、马来酸、柠康酸、富马酸、纳迪克酸、巴豆酸、异巴豆酸、乙酸乙烯酯、乙酸烯丙酯、肉桂酸、山梨酸、中康酸、偏苯三酸、均苯四酸、2,2’-3,3’-二苯甲酮四羧酸、3,3’-4,4’-二苯甲酮四羧酸、琥珀酸单[2-(甲基)丙烯酰氧基乙基]酯、邻苯二甲酸单[2-(甲基)丙烯酰氧基乙基]酯、ω-羧基聚己内酯单(甲基)丙烯酸酯等在两末端具有羧基和羟基的聚合物的单(甲基)丙烯酸酯、羟基乙基(甲基)丙烯酸酯-苹果酸酯、羟基丙基(甲基)丙烯酸酯-苹果酸酯、二环戊二烯-苹果酸酯或具有1个羧基和2个以上的(甲基)丙烯酰基的多官能(甲基)丙烯酸酯等不饱和多元酸;(甲基)丙烯酸-2-羟基乙酯、(甲基)丙烯酸-2-羟基丙酯、(甲基)丙烯酸缩水甘油酯、下述化合物No.25~No.28、(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸异壬酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸二甲基氨基甲酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸氨基丙酯、(甲基)丙烯酸二甲基氨基丙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸聚(乙氧基)乙酯、(甲基)丙烯酸丁氧基乙氧基乙酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸四氢呋喃酯、(甲基)丙烯酸乙烯基酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸苄酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三羟甲基乙烷三(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、季戊四醇五(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三环癸烷二羟甲基二(甲基)丙烯酸酯、三[(甲基)丙烯酰基乙基]异氰脲酸酯、聚酯(甲基)丙烯酸酯低聚物等不饱和一元酸和多元醇或多元酚的酯;(甲基)丙烯酸锌、(甲基)丙烯酸镁等不饱和多元酸的金属盐;马来酸酐、衣康酸酐、柠康酸酐、甲基四氢邻苯二甲酸酐、四氢邻苯二甲酸酐、三烷基四氢邻苯二甲酸酐、5-(2,5-二氧代四氢呋喃基)-3-甲基-3-环己烯-1,2-二羧酸酐、三烷基四氢邻苯二甲酸酐-马来酸酐加成物、十二碳烯基琥珀酸酐、甲基纳迪克酸酐等不饱和多元酸的酸酐;(甲基)丙烯酰胺、亚甲基双(甲基)丙烯酰胺、二乙三胺三(甲基)丙烯酰胺、苯二甲基双(甲基)丙烯酰胺、α-氯代丙烯酰胺、N-2-羟基乙基(甲基)丙烯酰胺等不饱和一元酸和多元胺的酰胺;丙烯醛等不饱和醛;(甲基)丙烯腈、α-氯代丙烯腈、偏二氰乙烯、烯丙基氰等不饱和腈;苯乙烯、4-甲基苯乙烯、4-乙基苯乙烯、4-甲氧基苯乙烯、4-羟基苯乙烯、4-氯苯乙烯、二乙烯基苯、乙烯基甲苯、乙烯基苯甲酸、乙烯基苯酚、乙烯基磺酸、4-乙烯基苯磺酸、乙烯基苄基甲基醚、乙烯基苄基缩水甘油醚等不饱和芳香族化合物;甲基乙烯基酮等不饱和酮;乙烯基胺、烯丙基胺、N-乙烯基吡咯烷酮、乙烯基哌啶等不饱和胺化合物;烯丙醇、巴豆醇等乙烯基醇;乙烯基甲基醚、乙烯基乙基醚、正丁基乙烯基醚、异丁基乙烯基醚、烯丙基缩水甘油醚等乙烯基醚;马来酰亚胺、N-苯基马来酰亚胺、N-环己基马来酰亚胺等不饱和酰亚胺类;茚、1-甲基茚等茚类;1,3-丁二烯、异戊二烯、氯丁二烯等脂肪族共轭二烯类;聚苯乙烯、聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸正丁酯、在聚硅氧烷等聚合物分子链的末端具有单(甲基)丙烯酰基的大分子单体类;氯乙烯、偏氯乙烯、琥珀酸二乙烯基酯、邻苯二甲酸二烯丙酯、磷酸三烯丙酯、三烯丙基异氰脲酸酯、乙烯基硫醚、乙烯基咪唑、乙烯基噁唑、乙烯基咔唑、乙烯基吡咯烷酮、乙烯基吡啶、含羟基的乙烯基单体和聚异氰酸酯化合物的乙烯基尿烷化合物、含羟基的乙烯基单体和聚环氧化合物的乙烯基环氧化合物。其中,对于在两末端具有羧基和羟基的聚合物的单(甲基)丙烯酸酯、具有1个羧基和2个以上的(甲基)丙烯酰基的多官能(甲基)丙烯酸酯、不饱和一元酸和多元醇或多元酚的酯来说,以本发明的肟酯化合物作为有效成分的光聚合引发剂是适合的。这些聚合性化合物可以单独使用或2种以上混合使用,而且当2种以上混合使用时,可以预先将它们共聚而作为共聚物来使用。
另外,作为上述具有烯键式不饱和键的聚合性化合物,也可以使用具有烯键式不饱和键的碱显影性化合物,将本发明的感光性组合物制成碱显影性感光性树脂组合物。作为该具有烯键式不饱和键的碱显影性化合物,可以使用丙烯酸酯的共聚物、苯酚和/或甲酚酚醛清漆环氧树脂、具有多官能环氧基的聚苯基甲烷型环氧树脂、以及使不饱和一元酸与下述通式(II)表示的环氧化合物等环氧化合物作用、进而使多元酸酐与其作用得到的树脂。其中,优选的是,使不饱和一元酸与下述通式(II)表示的环氧化合物等环氧化合物作用、进而使多元酸酐与其作用得到的树脂。
另外,上述具有烯键式不饱和键的碱显影性化合物优选含有0.2~1.0当量的不饱和基。
(式中,X1表示直接键合、亚甲基、碳原子数为1~4的烷叉基(亚烷基)、碳原子数为3~20的脂环式烃基、O、S、SO2、SS、SO、CO、OCO或下述[化学式33]或[化学式34]表示的取代基,该烷叉基(亚烷基)也可以被卤原子取代,R41、R42、R43和R44分别独立地表示氢原子、碳原子数为1~5的烷基、碳原子数为1~8的烷氧基、碳原子数为2~5的链烯基或卤原子,烷基、烷氧基和链烯基也可以被卤原子取代,m为0~10的整数。)
[化学式33]
(式中,Y1表示氢原子、也可以被碳原子数为1~10的烷基或烷氧基取代的苯基、或碳原子数为3~10的环烷基,Z1表示碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基或卤原子,烷基、烷氧基和链烯基也可以被卤原子取代,d为0~5的整数。)
[化学式34]
作为与上述环氧化合物作用的上述不饱和一元酸,可以列举出丙烯酸、甲基丙烯酸、巴豆酸、肉桂酸、山梨酸、羟基乙基甲基丙烯酸酯-苹果酸酯等。并可以列举出羟基乙基丙烯酸酯-苹果酸酯、羟基丙基甲基丙烯酸酯-苹果酸酯、羟基丙基丙烯酸酯-苹果酸酯、二环戊二烯-苹果酸酯等。
另外,作为在使上述不饱和一元酸作用后使其作用的上述多元酸酐,可以列举出联苯基四羧酸二酐、四氢邻苯二甲酸酐、琥珀酸酐、联苯四甲酸二酐、马来酸酐、偏苯三酸酐、均苯四酸酐、2,2’-3,3’-二苯甲酮四羧酸酐、乙二醇双偏苯三酸酐、丙三醇三偏苯三酸酐、六氢邻苯二甲酸酐、甲基四氢邻苯二甲酸酐、纳迪克酸酐、甲基纳迪克酸酐、三烷基四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、5-(2,5-二氧代四氢呋喃基)-3-甲基-3-环己烯-1,2-二羧酸酐、三烷基四氢邻苯二甲酸酐-马来酸酐加成物、十二碳烯基琥珀酸酐、甲基纳迪克酸酐等。
上述环氧化合物、上述不饱和一元酸和上述多元酸酐的反应摩尔比优选如下设定。即,相对于上述环氧化合物的1个环氧基,上述不饱和一元酸的羧基为0.1~1.0个,在具有以该比例加成后的结构的环氧加成物中,优选达到下述比例,相对于该环氧加成物的1个羟基,上述多元酸酐的酸酐结构为0.1~1.0个。
上述环氧化合物、上述不饱和一元酸和上述多元酸酐的反应可以按照常规方法来进行。
为了调整酸值以改善本发明的(着色)碱显影性感光性树脂组合物的显影性,与上述具有烯键式不饱和键的碱显影性化合物一起还可以使用单官能或多官能环氧化合物。上述具有烯键式不饱和键的碱显影性化合物的固体成分的酸值优选为5~120mgKOH/g的范围,单官能或多官能环氧化合物的使用量优选按照满足上述酸值的量来选择。
作为上述单官能环氧化合物,可以列举出甲基丙烯酸缩水甘油酯、甲基缩水甘油醚、乙基缩水甘油醚、丙基缩水甘油醚、异丙基缩水甘油醚、丁基缩水甘油醚、异丁基缩水甘油醚、叔丁基缩水甘油醚、戊基缩水甘油醚、己基缩水甘油醚、庚基缩水甘油醚、辛基缩水甘油醚、壬基缩水甘油醚、癸基缩水甘油醚、十一烷基缩水甘油醚、十二烷基缩水甘油醚、十三烷基缩水甘油醚、十四烷基缩水甘油醚、十五烷基缩水甘油醚、十六烷基缩水甘油醚、2-乙基己基缩水甘油醚、烯丙基缩水甘油醚、炔丙基缩水甘油醚、对甲氧基乙基缩水甘油醚、苯基缩水甘油醚、对甲氧基缩水甘油醚、对丁基苯酚缩水甘油醚、甲苯基缩水甘油醚、2-甲基甲苯基缩水甘油醚、4-壬基苯基缩水甘油醚、苄基缩水甘油醚、对枯基苯基缩水甘油醚、三苯甲基缩水甘油醚、甲基丙烯酸2,3-环氧丙酯、环氧化大豆油、环氧化亚麻仁油、丁酸缩水甘油酯、乙烯基环己烷一氧化物、1,2-环氧-4-乙烯基环己烷、氧化苯乙烯、氧化蒎烯、氧化甲基苯乙烯、氧化环己烯、氧化丙烯、下述化合物No.29、No.30等。
作为上述多官能环氧化合物,如果使用选自双酚型环氧化合物和缩水甘油醚类之中的一种以上,则可以得到特性更好的着色碱显影性感光性树脂组合物,因而优选。作为该双酚型环氧化合物,除了可以使用上述通式(II)表示的环氧化合物之外,还可以使用例如加氢双酚型环氧化合物等双酚型环氧化合物。作为该缩水甘油醚类,可以列举出乙二醇二缩水甘油醚、丙二醇二缩水甘油醚、1,4-丁二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、1,8-辛二醇二缩水甘油醚、1,10-癸二醇二缩水甘油醚、2,2-二甲基-1,3-丙二醇二缩水甘油醚、二乙二醇二缩水甘油醚、三乙二醇二缩水甘油醚、四乙二醇二缩水甘油醚、六乙二醇二缩水甘油醚、1,4-环己烷二甲醇二缩水甘油醚、1,1,1-三(缩水甘油氧基甲基)丙烷、1,1,1-三(缩水甘油氧基甲基)乙烷、1,1,1-三(缩水甘油氧基甲基)甲烷、1,1,1,1-四(缩水甘油氧基甲基)甲烷。
除此之外,还可以使用苯酚酚醛清漆型环氧化合物、联苯酚醛清漆型环氧化合物、甲酚酚醛清漆型环氧化合物、双酚A酚醛清漆型环氧化合物、二环戊二烯酚醛清漆型环氧化合物等酚醛清漆型环氧化合物;3,4-环氧-6-甲基环己基甲基-3,4-环氧-6-甲基环己烷羧酸酯、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、1-环氧乙基-3,4-环氧环己烷等脂环式环氧化合物;邻苯二甲酸二缩水甘油酯、四氢化邻苯二甲酸二缩水甘油酯、二聚酸缩水甘油酯等缩水甘油酯类;四缩水甘油基二氨基二苯基甲烷、三缩水甘油基对氨基苯酚、N,N-二缩水甘油基苯胺等缩水甘油基胺类;1,3-二缩水甘油基-5,5-二甲基乙内酰脲、三缩水甘油基异氰脲酸酯等杂环式环氧化合物;二氧化二环戊二烯等二氧化物;萘型环氧化合物、三苯基甲烷型环氧化合物、二环戊二烯型环氧化合物等。
在本发明的感光性组合物中,光聚合引发剂的添加量没有特别限定,本发明的肟酯化合物的添加量为,相对于100质量份的具有烯键式不饱和键的上述聚合性化合物,优选为1~70质量份,更优选为1~50质量份,最优选为5~30质量份。
特别是在将本发明的感光性组合物制成(着色)碱显影性感光性树脂组合物的情况下,具有烯键式不饱和键的上述碱显影性化合物的含量为,优选在本发明的(着色)碱显影性感光性树脂组合物中为1~20质量%,特别优选为3~12质量%。
本发明的感光性组合物中还可以进一步添加溶剂。作为该溶剂,通常是能够根据需要溶解或分散上述各成分(本发明的肟酯化合物和具有烯键式不饱和键的聚合性化合物等)的溶剂,可以列举出例如甲乙酮、甲基戊基酮、二乙酮、丙酮、甲基异丙基酮、甲基异丁基酮、环己酮等酮类;乙醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲醚等醚系溶剂;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯等酯系溶剂;乙二醇单甲醚、乙二醇单乙醚、丙二醇单甲醚乙酸酯等溶纤剂系溶剂;甲醇、乙醇、异或正丙醇、异或正丁醇、戊醇等醇系溶剂;乙二醇单甲基乙酸酯、乙二醇单乙基乙酸酯、丙二醇甲基乙酸酯等醚酯系溶剂;苯、甲苯、二甲苯等BTX系溶剂;己烷、庚烷、辛烷、环己烷等脂肪族烃系溶剂;松节油、D-柠檬烯、蒎烯等萜烯系烃油;矿油精、Swazol#310(Cosmo松山石油株式会社)、Solvesso#100(Exxon化学株式会社)等链烷烃系溶剂;四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等卤代脂肪族烃系溶剂;氯苯等卤代芳香族烃系溶剂;卡必醇系溶剂、苯胺、三乙胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲亚砜、水等,这些溶剂可以使用1种,也可以使用2种以上的混合溶剂。
其中酮类、溶纤剂系溶剂等特别是丙二醇-1-单甲醚-2-乙酸酯、环己酮等使得在感光性组合物中抗蚀剂和光聚合引发剂的相容性良好,因而优选。
本发明的感光性组合物中还可以进一步含有无机化合物。作为该无机化合物,可以列举出例如氧化镍、氧化铁、氧化铱、氧化钛、氧化锌、氧化镁、氧化钙、氧化钾、二氧化硅、氧化铝等金属氧化物;层状粘土矿物、米洛丽蓝、碳酸钙、碳酸镁、钴系、锰系、玻璃粉末、云母、滑石、高岭土、亚铁氰化物、各种金属硫酸盐、硫化物、硒化物、硅酸铝、硅酸钙、氢氧化铝、铂、金、银、铜等,其中,优选氧化钛、二氧化硅、层状粘土矿物、银等。本发明的感光性组合物中,无机化合物的含量是,相对于具有烯键式不饱和键的上述聚合性化合物100质量份优选为0.1~50质量份,更优选为0.5~20质量份,这些无机化合物可以使用1种或2种以上。
上述无机化合物可以用作例如填充剂、防反射剂、导电剂、稳定剂、阻燃剂、机械强度提高剂、特殊波长吸收剂、防油墨剂等。
另外,本发明的感光性组合物(特别是碱显影性感光性树脂组合物)中可以进一步含有色料而成为着色感光性组合物。作为该色料,可以列举出颜料、染料、天然色素等。这些色料可以单独使用或者2种以上混合使用。
作为上述颜料,可以使用例如亚硝基化合物、硝基化合物、偶氮化合物、重氮化合物、氧杂蒽化合物、喹啉化合物、蒽醌化合物、香豆素化合物、酞菁化合物、异吲哚啉酮化合物、异吲哚啉化合物、喹吖酮化合物、二并蒽酮化合物、紫环酮(perynone)化合物、二萘嵌苯化合物、二氧代吡咯并吡咯化合物、硫靛化合物、二噁嗪化合物、三苯基甲烷化合物、喹酞酮化合物、萘四羧酸;偶氮染料、菁染料的金属络合物;色淀颜料;用炉法、槽法、热裂解法得到的炭黑、或乙炔黑、科琴黑或灯黑等炭黑;将上述炭黑进行酸性或碱性表面处理而得到的物质;石墨、石墨化炭黑、活性炭、碳纤维、碳纳米管、螺旋状碳纤维、碳纳米突、碳气凝胶、富勒烯、苯胺黑、颜料黑7、钛黑;疏水性树脂、氧化铬绿、米洛丽蓝、钴绿、钴蓝、锰系、亚铁氰化物、磷酸盐群青、普鲁土蓝、群青、钴天蓝、浓绿色颜料、翡翠绿、硫酸铅、铬黄、锌黄、氧化铁(红色氧化铁(III))、镉红、合成铁黑、棕土(amber)等有机或无机颜料。这些颜料可以单独使用或多种混合使用。
作为上述颜料,还可以使用市售的颜料,可以列举出例如颜料红1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、228、240、254;颜料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;颜料黄1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180、185;颜料绿7、10、36;颜料蓝15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;颜料紫1、19、23、27、29、30、32、37、40、50等。
作为上述染料,可以列举出偶氮染料、蒽醌染料、靛类染料、三芳基甲烷染料、氧杂蒽染料、茜素染料、吖啶染料、茋染料、噻唑染料、萘酚染料、喹啉染料、硝基染料、吲达胺染料、噁嗪染料、酞菁染料、菁染料等染料等,它们也可以多种混合使用。
在本发明的感光性组合物中,上述色料的添加量是,相对于100质量份的具有烯键式不饱和键的上述聚合性化合物优选为50~350质量份,更优选为100~250质量份。
此外,通过在使用具有烯键式不饱和键的上述聚合性化合物的同时,使用其它的有机聚合物,还可以改善固化物的特性。作为该有机聚合物,可以列举出例如聚苯乙烯、聚甲基丙烯酸甲酯、甲基丙烯酸甲酯-丙烯酸乙酯共聚物、聚(甲基)丙烯酸、苯乙烯-(甲基)丙烯酸共聚物、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、乙烯-氯乙烯共聚物、乙烯-乙烯基共聚物、聚氯乙烯树脂、ABS树脂、尼龙6、尼龙66、尼龙12、聚氨酯树脂、聚碳酸酯聚乙烯醇缩丁醛、纤维素酯、聚丙烯酰胺、饱和聚酯、酚醛树脂、苯氧基树脂、聚酰胺酰亚胺树脂、聚酰胺酸树脂、环氧树脂等,其中优选聚苯乙烯、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、环氧树脂。
在使用其它有机聚合物时,其用量相对于100质量份的具有烯键式不饱和键的上述聚合性化合物,优选为10~500质量份。
本发明的感光性组合物中可以进一步并用具有不饱和键的单体、链转移剂、表面活性剂等。
作为上述具有不饱和键的单体,可以列举出丙烯酸-2-羟基乙酯、丙烯酸-2-羟基丙酯、丙烯酸异丁酯、丙烯酸正辛酯、丙烯酸异辛酯、丙烯酸异壬酯、丙烯酸硬脂酯、丙烯酸甲氧基乙酯、丙烯酸二甲基氨基乙酯、丙烯酸锌、1,6-己二醇二丙烯酸酯、三羟甲基丙烷三丙烯酸酯、甲基丙烯酸-2-羟基乙酯、甲基丙烯酸-2-羟基丙酯、甲基丙烯酸丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸环己酯、三羟甲基丙烷三甲基丙烯酸酯、二季戊四醇五丙烯酸酯、二季戊四醇六丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三丙烯酸酯、双酚A二缩水甘油醚(甲基)丙烯酸酯、双酚F二缩水甘油醚(甲基)丙烯酸酯、双酚Z二缩水甘油醚(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯等。
作为上述链转移剂,可以列举出巯基乙酸、硫代苹果酸、邻巯基苯甲酸、2-巯基丙酸、3-巯基丙酸、3-巯基丁酸、N-(2-巯基丙酰基)甘氨酸、2-巯基烟酸、3-[N-(2-巯基乙基)氨基甲酰基]丙酸、3-[N-(2-巯基乙基)氨基]丙酸、N-(3-巯基丙酰基)丙氨酸、2-巯基乙磺酸、3-巯基丙磺酸、4-巯基丁磺酸、十二烷基(4-甲硫基)苯基醚、2-巯基乙醇、3-巯基-1,2-丙二醇、1-巯基-2-丙醇、3-巯基-2-丁醇、巯基苯酚、2-巯基乙胺、2-巯基咪唑、2-巯基-3-吡啶酚、2-巯基苯并噻唑、巯基乙酸、三羟甲基丙烷三(3-巯基丙酸酯)、季戊四醇四(3-巯基丙酸酯)等巯基化合物、将该巯基化合物氧化而得到的二硫化物、碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸、3-碘丙磺酸等碘化烷基化合物。
作为上述表面活性剂,可以使用全氟烷基磷酸酯、全氟烷基羧酸盐等含氟表面活性剂、高级脂肪酸碱盐、烷基磺酸盐、烷基硫酸盐等阴离子系表面活性剂;高级胺卤代酸盐、季铵盐等阳离子系表面活性剂;聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨糖醇酐脂肪酸酯、脂肪酸单甘油酯等非离子表面活性剂;两性表面活性剂;硅酮系表面活性剂等表面活性剂,它们也可以组合起来使用。
此外,本发明的感光性组合物中,作为光聚合引发剂,除了本发明的肟酯化合物以外,根据需要还可以并用其它的光聚合引发剂或增感剂,有时通过并用其它光聚合引发剂可以起到显著的协同效应。
作为可以与本发明的肟酯化合物并用的光聚合引发剂,可以使用以往已知的化合物,可以列举出例如二苯甲酮、苯基联苯酮、1-羟基-1-苯酰基环己烷、苯偶姻、苯偶酰双甲醚、1-苄基-1-二甲胺基-1-(4’-吗啉代苯酰基)丙烷、2-吗啉基-2-(4’-甲基巯基)苯酰基丙烷、噻吨酮、1-氯-4-丙氧基噻吨酮、异丙基噻吨酮、二乙基噻吨酮、乙基蒽醌、4-苯酰基-4’-甲基二苯基硫化物、苯偶姻丁醚、2-羟基-2-苯酰基丙烷、2-羟基-2-(4’-异丙基)苯酰基丙烷、4-丁基苯酰基三氯甲烷、4-苯氧基苯酰基二氯甲烷、苯酰基甲酸甲酯、1,7-双(9’-吖啶基)庚烷、9-正丁基-3,6-双(2’-吗啉代异丁酰基)咔唑、2-甲基-4,6-双(三氯甲基)-s-三嗪、2-苯基-4,6-双(三氯甲基)-s-三嗪、2-萘基-4,6-双(三氯甲基)-s-三嗪、2,2-双(2-氯苯基)-4,5,4’,5’-四苯基-1-2’-联咪唑、4,4-偶氮二异丁腈、三苯基膦、樟脑醌、N-1414、N-1717、N-1919、PZ-408(ADEKA株式会社制造)、IRGACURE369、IRGACURE907、IRGACURE OXE 01、IRGACURE OXE 02(Ciba SpecialtyChemicals株式会社制造)、过氧化苯甲酰、下述通式(III)~(V)表示的化合物等,这些光聚合引发剂可以使用1种或组合2种以上使用。在使用这些其它的光聚合引发剂时,其使用量优选设定为本发明的肟酯化合物的使用量的1质量倍以下。
(式中,R1和R2的定义与上述通式(I)相同,R6与R1相同,Y2表示卤原子或烷基,n为0~5。)
(式中,R1和R2的定义与上述通式(I)相同,R6、Y2和n的定义与上述通式(III)相同,R’1、R’2和R’6与R1相同,Y’2与Y2相同,R7表示二醇残基或二硫醇残基,Z2表示氧原子或硫原子。)
(式中,R1和R2的定义与上述通式(I)相同,R6、Y2和n的定义与上述通式(III)相同,Z3表示氧原子、硫原子或硒原子,A表示杂环基,p为0~5的整数,q为0或1。)
此外,在本发明的感光性组合物中,根据需要可以加入对苯甲醚、氢醌、焦儿茶酚、叔丁基儿茶酚、吩噻嗪等热聚合抑制剂;增塑剂;粘接促进剂;填充剂;消泡剂;流平剂;表面调整剂;抗氧化剂;紫外线吸收剂;分散助剂;抗凝剂;催化剂;效果促进剂;增感剂;交联剂;增粘剂等惯用的添加物。
本发明的感光性组合物中,具有烯键式不饱和键的上述聚合性化合物和本发明的肟酯化合物以外的任意成分(但是上述的其它光聚合引发剂、无机填充剂、色料以及溶剂除外)的使用量可以根据其使用目的而适当地选择,并没有特别限制,但优选相对于100质量份的具有烯键式不饱和键的上述聚合性化合物,合计为50质量份以下。
本发明的感光性组合物可以通过旋涂器、辊涂器、棒涂器、模涂器、帘式涂布器、各种印刷、浸渍等公知的手段应用于钠玻璃、石英玻璃、半导体基板、金属、纸、塑料等支撑基体上。此外,也可以暂时在薄膜等支撑基体上实施后,转印到其它支撑基体上,其应用方法没有限制。
本发明的感光性组合物可以用于光固化性涂料或清漆、光固化性粘接剂、印制电路板或彩色电视机、PC监视器、便携信息终端、数码相机等彩色显示的液晶显示元件中的滤色器、等离子体显示面板用的电极材料、粉末涂料、印刷油墨、印刷版、粘接剂、牙科用组合物、凝胶涂层、电子工程学用的光致抗蚀剂、电镀抗蚀剂、蚀刻抗蚀剂、液状和干燥膜这两者、焊锡抗蚀剂、用于制造各种显示用途用的滤色器或在等离子体显示面板、电发光显示装置以及LCD的制造工序中用于形成结构的抗蚀剂、用于密封电气或电子部件的组合物、磁记录材料、微小机械部件、波导、光学开关、镀覆用掩模、蚀刻掩模、显色试验系、玻璃纤维电缆涂层、丝网印刷用模版、用于通过立体平版印刷制造三维物体的材料、全息照相记录用材料、图像记录材料、微细电路、脱色材料、用于图像记录材料的脱色材料、使用微囊的图像记录材料用的脱色材料、印制电路板用光致抗蚀剂材料、UV和可见激光直接图像系用的光致抗蚀剂材料、用于形成印制电路基板的逐次叠层中的电介体层的光致抗蚀剂材料或保护膜等各种用途中,其用途并没有特别限制。
此外,作为使含有本发明的肟酯化合物的感光性组合物进行硬化时所使用的活性光的光源,可以使用发出波长为300~450nm的光的光源,例如可以使用超高压汞、汞蒸汽弧、碳弧、氙弧等。
实施例
下面通过列举实施例等对本发明进行更详细的说明,但是本发明并不限定于这些实施例。
[实施例1]化合物No.1的制造。
<步骤1>硫化物的制造
在氮气氛下加入对氯硝基苯31.6g(200毫摩尔)、苯硫酚24.2g(220毫摩尔)和二甲基乙酰胺139g,加入氢氧化钠25.0g(300毫摩尔)后在50℃下搅拌1小时。冷却至室温,用乙酸乙酯/水系进行油水分离。馏去溶剂,得到黄色晶体46.2g(收率99%、HPLC纯度99%)。
<步骤2>酰基体的制造
在氮气氛下加入氯化铝64.0g(480毫摩尔)和二氯乙烷186g,在冰冷下缓慢滴加苯基乙酰氯27.8g(180毫摩尔),然后缓慢滴加实施例1的步骤1得到硫化物34.7g(150毫摩尔)和二氯乙烷186g,在5℃下搅拌30分钟。将反应液倒入至冰水中,进行油水分离。经过脱溶剂、从氯仿/甲醇混合溶剂中的再结晶后得到淡褐色晶体12.0g(收率19%、HPLC纯度98%)。
<步骤3>化合物No.1的制造
在氮气流下加入实施例1的步骤2得到的酰基体11.5g(33毫摩尔)以及二甲基甲酰胺6.24g,滴加甲醇钠3.18g(16.5毫摩尔),在水浴下于10℃滴加亚硝酸异戊酯3.13g(36.3毫摩尔),在10~20℃下搅拌1小时。加入乙酸丁酯和5%盐酸进行油水分离。馏去溶剂,在剩下的部分中加入乙酸丁酯42.0g、然后加入乙酸酐3.71g(36.3毫摩尔),在90℃下搅拌1小时,冷却至室温。用5%氢氧化钠水溶液进行中和,经过油水分离、脱溶剂、从乙酸丁酯/二丁基醚混合溶剂中的再结晶后得到淡黄色晶体6.11g(收率44%、HPLC纯度99%)。对该淡黄色晶体进行了各种分析,结果确认了该淡黄色晶体是目标物的化合物No.1。分析结果如下所示。
(分析结果)
(1)熔点:92.3℃
(2)1H-NMR测定:(ppm)
2.21(s:3H)、7.43-7.51(m:7H)、7.59(d:1H)、7.60(d:1H)、8.12(d:2H)、8.17(d:2H)
(3)IR测定:(cm-1)
3433、3060、1779、1676、1586、1518、1475、1446、1405、1340、1276、1215、1179、1080、1012、902、850、776、742、692、663
(4)UV光谱测定(氯仿)
λmax=346nm
(5)分解温度测定(在氮气气氛下,升温速度为10℃/分钟,重量减少5%时的温度)
241.4℃
[实施例1B]化合物No.15的制造
<步骤1>酰基体的制造
在氮气氛下加入氯化铝3.52g(26.4毫摩尔)和二氯乙烷16g,在冰冷下缓慢滴加苯基乙酰氯2.041g(13.2毫摩尔),然后缓慢滴加3-硝基-N-辛基咔唑3.893g(12毫摩尔)和二氯乙烷16g,在5℃下搅拌30分钟。将反应液倒入至冰水中,进行油水分离。经过脱溶剂、从氯仿/甲醇混合溶剂中的再结晶后得到黄色晶体3.889g(收率73%、HPLC纯度99%)。
<步骤2>化合物No.15的制造
在氮气流下加入实施例1B的步骤1得到的酰基体3.762g(8.5毫摩尔)以及二甲基甲酰胺6.24g,滴加甲醇钠0.820g(4.25毫摩尔),在水浴下于10℃滴加亚硝酸异戊酯0.806g(9.35毫摩尔),在10~20℃下搅拌1小时。加入乙酸丁酯和5%盐酸进行油水分离。馏去溶剂,在剩下的部分中加入乙酸丁酯13.0g、然后加入乙酸酐0.955g(9.35毫摩尔),在90℃下搅拌1小时,冷却至室温。用5%氢氧化钠水溶液进行中和,经过油水分离、脱溶剂、从乙酸丁酯/二丁基醚混合溶剂中的再结晶后得到无色晶体1.725g(收率40%、HPLC纯度99%)。对该无色晶体进行了各种分析,结果确认了该无色晶体是目标物的化合物No.15。分析结果如下所示。
(分析结果)
(1)熔点:145.2℃
(2)1H-NMR测定:(ppm)
0.86(t:3H)、1.18-1.43(m:10H)、1.91(tt:2H)、2.01(s:3H)、4.39(t:2H)、7.43(ddd:2H)、7.50(d:1H)、7.51(dddd:1H)、7.56(d:1H)、7.82(ddd:2H)、8.19(dd:1H)、8.45(dd:1H)、8.73(s:1H)、9.04(s:1H)
(3)IR测定:(cm-1)
3436、2927、1787、1669、1628、1596、1520、1482、1334、1234、1179、1146、1128、1092、912、889、826、759、727、696、658
(4)UV光谱测定(氯仿)
λmax=364nm
(5)分解温度测定(在氮气气氛下,升温速度为10℃/分钟,重量减少5%时的温度)
269.2℃
[实施例2]感光性组合物No.1的调制
在丙烯酸系共聚物14.0g中加入5.90g三羟甲基丙烷三丙烯酸酯、2.70g实施例1得到的化合物No.1以及79.0g乙基溶纤剂,充分搅拌,得到感光性组合物No.1。
另外,上述丙烯酸系共聚物通过如下方法得到:将20质量份甲基丙烯酸、15质量份甲基丙烯酸羟基乙酯、10质量份甲基丙烯酸甲酯和55质量份甲基丙烯酸丁酯溶解于300质量份乙基溶纤剂中,在氮气氛下加入0.75质量份偶氮二异丁腈后在70℃下反应5小时,由此得到上述丙烯酸系共聚物。
[实施例3]感光性组合物No.2的调制
将15.0g二季戊四醇五丙烯酸酯和3.74g 1,4-丁二醇二缩水甘油醚进行混合,添加3.30g实施例1得到的化合物No.1和78g乙基溶纤剂,充分搅拌,得到感光性组合物No.2。
[实施例4]作为碱显影性感光性树脂组合物的感光性组合物No.3的调制
<步骤1>碱显影性树脂组合物No.3的调制
加入1,1-双(4’-环氧丙氧基苯基)-1-(1”-联苯基)-1-环己基甲烷17.0g、丙烯酸4.43g、2,6-二叔丁基-对甲酚0.06g、四丁基乙酸铵0.11g和丙二醇-1-单甲醚-2-乙酸酯14.3g,在120℃下搅拌16小时。冷却至室温,加入丙二醇-1-单甲醚-2-乙酸酯7.18g、琥珀酸酐4.82g和四丁基乙酸铵0.25g,在100℃下搅拌5小时。进而,加入1,1-双(4’-环氧丙氧基苯基)-1-(1”-联苯基)-1-环己基甲烷5.08g和丙二醇-1-单甲醚-2-乙酸酯2.18g,在120℃下搅拌12小时,在80℃下搅拌2小时,在40℃下搅拌2小时后,加入丙二醇-1-单甲醚-2-乙酸酯13.1g,作为丙二醇-1-单甲醚-2-乙酸酯溶液,得到目标物的碱显影性树脂组合物No.3(Mw=4200、Mn=2100、酸值(固体成分)55mgKOH/g)。
<步骤2>感光性组合物No.3的调制
将2.68g实施例4的步骤1得到的碱显影性树脂组合物No.3、0.73g三羟甲基丙烷三丙烯酸酯、7.91g丙二醇-1-单甲醚-2-乙酸酯和5.18g环己酮进行混合,添加1.58g实施例1得到的化合物No.1,充分搅拌,得到作为碱显影性感光性树脂组合物的感光性组合物No.3。
[实施例5]作为碱显影性感光性树脂组合物的感光性组合物No.4的调制
<步骤1>碱显影性树脂组合物No.4的调制
加入双酚芴型环氧树脂(环氧当量为231)184g、丙烯酸58.0g、2,6-二叔丁基-对甲酚0.26g、四丁基乙酸铵0.11g和丙二醇-1-单甲醚-2-乙酸酯23.0g,在120℃下搅拌16小时。冷却至室温,加入丙二醇-1-单甲醚-2-乙酸酯35.0g、联苯四甲酸二酐59.0g和四正丁基溴化铵0.24g,在120℃下搅拌4小时。进而,加入四氢邻苯二甲酸酐20g,在120℃下搅拌4小时,在100℃下搅拌3小时,在80℃下搅拌4小时,在60℃下搅拌6小时,在40℃下搅拌11小时后,加入丙二醇-1-单甲醚-2-乙酸酯90.0g,作为丙二醇-1-单甲醚-2-乙酸酯溶液,得到目标物的碱显影性树脂组合物No.4(Mw=5000、Mn=2100、酸值(固体成分)92.7mgKOH/g)。
<步骤2>感光性组合物No.4的调制
将2.68g实施例5的步骤1得到的碱显影性树脂组合物No.4、0.73g三羟甲基丙烷三丙烯酸酯、7.91g丙二醇-1-单甲醚-2-乙酸酯和5.18g环己酮进行混合,添加1.58g实施例1得到的化合物No.1,充分搅拌,得到作为碱显影性感光性树脂组合物的感光性组合物No.4。
[实施例6]作为着色碱显影性感光性树脂组合物的感光性组合物No.5的调制
除了进一步加入2.00g颜料蓝15之外,与实施例4同样地得到作为着色碱显影性感光性树脂组合物的感光性组合物No.5。
[实施例7]作为着色碱显影性感光性树脂组合物的感光性组合物No.6的调制
除了进一步加入3.00g炭黑之外,与实施例5同样地得到作为着色碱显影性感光性树脂组合物的感光性组合物No.6。
[实施例8]感光性组合物No.9的调制
除了进一步加入4.52g氧化钛之外,与实施例2同样地得到感光性组合物No.9。
[比较例1]感光性组合物No.7的制造
代替实施例1得到的化合物No.1,使用3.30g下述[化学式40]所示的比较化合物1,除此以外,与实施例3同样地得到比较用的感光性组合物No.7。
[化学式40]
[比较例2]作为碱显影性感光性树脂组合物的感光性组合物No.8的制造
除了使用1.58g比较化合物1代替1.58g实施例1得到的化合物No.1之外,与实施例4同样地得到作为比较用的碱显影性感光性树脂组合物的感光性组合物No.8。
对得到的感光性组合物No.2和比较用的感光性组合物No.7如下地进行硬度试验。试验结果示于表1中。
另外,对作为碱显影性感光性树脂组合物的感光性组合物No.3和作为比较用的碱显影性感光性树脂组合物的感光性树脂组合物No.8如下地进行灵敏度评价。试验结果示于表2中。
<硬度试验>
用#3的棒涂器将感光性组合物涂布于厚度为50μm的聚对苯二甲酸乙二醇酯薄膜上。使用带有带式传输机的光照射装置对其照射80W/cm的高压汞灯的光。从灯至带式传输机的距离设为10cm,带式传输机的线速度设为8cm/分钟。固化后在室温下放置24小时,然后使用铅笔硬度试验机测定负荷为1kg时的铅笔硬度。
<灵敏度>
用#3的棒涂器将碱显影性感光性树脂组合物以大约1μm的厚度涂布于铝基板上。在60℃下预烘焙15分钟后,利用日本分光株式会社制造的分光照射装置CT-25CP并使用超高压汞灯作为光源进行曝光,然后在25℃下浸渍于2.5质量%碳酸钠溶液中进行显影,充分水洗,测定365nm和405nm的分光灵敏度。灵敏度是指,由铝板上残留的固化膜层数和365nm及405nm的射出光量求出的在365nm及405nm的光下固化所需的最小固化能量。
表1
感光性组合物 | 铅笔硬度 |
No.2(实施例3) | 3H |
No.7(比较例1) | 1H |
表2
实施例3的感光性组合物No.2的硬度较高,但比较例1的感光性组合物No.7不能得到充分的硬度。
另外,实施例4的碱显影性感光性树脂组合物No.3对于长波长的365nm和405nm的光具有优良的灵敏度,但比较例2的碱显影性感光性树脂组合物No.8由于对365nm和405nm的光的灵敏度低,所以不得不加大曝光量。
本发明的肟酯化合物由于具有优良的感光性,特别是对长波长的365nm(i线)和405nm(h线)的亮线具有优良的灵敏度,所以作为光聚合引发剂是有用的。
Claims (8)
1、一种由下述通式(I)表示的肟酯化合物,
式中,R1和R2分别独立地表示R11、OR11、COR11、SR11、CONR12R13或CN,R11、R12和R13分别独立地表示氢原子、碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳烷基或碳原子数为2~20的杂环基,烷基、芳基、芳烷基和杂环基的氢原子进而还可以被OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、CN、卤原子、-CR21=CR22R23、-CO-CR21=CR22R23、羧基、环氧基取代,R21、R22和R23分别独立地表示氢原子、碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳烷基或碳原子数为2~20的杂环基,所述R11、R12、R13、R21、R22和R23表示的取代基的亚烷基部分的亚甲基也可以被不饱和键、醚键、硫醚键、酯键、硫酯键、酰胺键或氨基甲酸酯键中断1~5次,所述取代基的烷基部分可以具有分支侧链,也可以是环状烷基,所述取代基的烷基末端也可以是不饱和键,而且,R12和R13、以及R22和R23也可以分别一起形成环,R3和R4分别独立地表示R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11、CN、卤原子或羟基,a和b分别独立地为0~4,X表示氧原子、硫原子、硒原子、CR31R32、CO、NR33或PR34,R31、R32、R33和R34分别独立地表示R11、OR11、COR11、SR11、CONR12R13或CN,R3也可以通过-X-与邻接的苯环的一个碳原子结合而形成环结构,或者R3和R4也可以一起形成环,R31、R33和R34也可以分别独立地与邻接的任何一个苯环一起形成环。
2、根据权利要求1所述的肟酯化合物,其中,所述通式(I)中的X是硫原子或NR33;R33可以具有分支侧链,也可以是环状烷基,且是也可以被卤原子取代的碳原子数为1~20的烷基。
3、根据权利要求1或2所述的肟酯化合物,其中,所述通式(I)中的R1是也可以被卤原子取代的碳原子数为6~30的芳基;R2也可以是环状烷基,且是也可以被卤原子取代的碳原子数为1~20的烷基。
4、一种光聚合引发剂,其以权利要求1~3中任一项所述的肟酯化合物作为有效成分。
5、一种感光性组合物,其含有权利要求4所述的光聚合引发剂和具有烯键式不饱和键的聚合性化合物。
6、根据权利要求5所述的感光性组合物,其进一步含有无机化合物。
7、一种碱显影性感光性树脂组合物,其含有权利要求4所述的光聚合引发剂和具有烯键式不饱和键的碱显影性化合物。
8、一种着色碱显影性感光性树脂组合物,其是在权利要求7所述的碱显影性感光性树脂组合物中进一步含有色料而形成的。
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