CN101855201B - 肟酯化合物及含有该化合物的光聚合引发剂 - Google Patents
肟酯化合物及含有该化合物的光聚合引发剂 Download PDFInfo
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- CN101855201B CN101855201B CN2007801015233A CN200780101523A CN101855201B CN 101855201 B CN101855201 B CN 101855201B CN 2007801015233 A CN2007801015233 A CN 2007801015233A CN 200780101523 A CN200780101523 A CN 200780101523A CN 101855201 B CN101855201 B CN 101855201B
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- -1 Oxime esters Chemical class 0.000 title claims abstract description 140
- 239000003999 initiator Substances 0.000 title abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 101
- 239000002131 composite material Substances 0.000 claims description 63
- 239000003513 alkali Substances 0.000 claims description 33
- 239000011342 resin composition Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- 235000010755 mineral Nutrition 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
- 239000011572 manganese Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- VRWKTAYJTKRVCU-UHFFFAOYSA-N iron(6+);hexacyanide Chemical compound [Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] VRWKTAYJTKRVCU-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002734 clay mineral Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 229960001866 silicon dioxide Drugs 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- UTYXJYFJPBYDKY-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide;trihydrate Chemical compound O.O.O.[K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UTYXJYFJPBYDKY-UHFFFAOYSA-N 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000292 calcium oxide Substances 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- HTXDPTMKBJXEOW-UHFFFAOYSA-N dioxoiridium Chemical compound O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910000457 iridium oxide Inorganic materials 0.000 claims description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
- 229960001708 magnesium carbonate Drugs 0.000 claims description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 2
- 235000014380 magnesium carbonate Nutrition 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims description 2
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 claims description 2
- 229910001950 potassium oxide Inorganic materials 0.000 claims description 2
- 150000003346 selenoethers Chemical class 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 235000012222 talc Nutrition 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 16
- 230000035945 sensitivity Effects 0.000 abstract description 13
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052711 selenium Inorganic materials 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000031700 light absorption Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000011669 selenium Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 239000000049 pigment Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000975 dye Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 150000007518 monoprotic acids Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 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 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 235000013824 polyphenols Nutrition 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 229960001701 chloroform Drugs 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 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
- 229930185605 Bisphenol Natural products 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- 229920001577 copolymer Polymers 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 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
- 238000000926 separation method Methods 0.000 description 4
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
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- 125000001118 alkylidene group Chemical group 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
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- 229910052731 fluorine Inorganic materials 0.000 description 3
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- 229910052753 mercury Inorganic materials 0.000 description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 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
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- 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
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- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- 238000012719 thermal polymerization Methods 0.000 description 1
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- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
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Abstract
本发明的肟酯化合物以下述通式(I)表示,其作为光聚合引发剂是有用的。以该肟酯化合物为有效成分的光聚合引发剂高效地吸收405nm或365nm等长波长的光而活化,显示高感度。通式中,R1及R2表示R11、OR11、COR11、SR11、CONR12R13或CN,R11~R13表示氢原子、C1~20烷基、C6~30芳基、C7~30芳烷基或C2~20杂环基,R3及R4表示R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11、CN、卤原子或羟基,a及b为0~4,X表示氧原子、硫原子、硒原子、CR31R32、CO、NR33或PR34,R31~R34与R1相同。
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有用的新型肟酯化合物、以该肟酯化合物为有效成分的光聚合引发剂、以及在具有烯属不饱和键的聚合性化合物中含有该光聚合引发剂而成的感光性组合物。
背景技术
感光性组合物是在具有烯属不饱和键的聚合性化合物中添加光聚合引发剂而得到的组合物,由于通过对该感光性组合物照射405nm或365nm的光能够使其聚合固化,因此该组合物被用于光固化性油墨、感光性印刷版、各种光致抗蚀剂等中。
作为上述感光性组合物中使用的光聚合引发剂,下述专利文献1~8提出了具有咔唑基结构的O-酰基肟化合物。但是,这些公知的O-酰基肟化合物特别是在感度方面无法充分满足要求。
专利文献1:日本特开2001-302871号公报
专利文献2:日本特表2004-534797号公报
专利文献3:日本特开2005-25169号公报
专利文献4:日本特开2005-128483号公报
专利文献5:日本特开2005-242279号公报
专利文献6:日本特开2005-242280号公报
专利文献7:日本特开2006-16545号公报
专利文献8:日本专利第3754065号公报
发明内容
本发明所要解决的问题在于目前还没有具有令人满意的感度的光聚合引发剂。
因此,本发明的目的在于提供高效地吸收405nm或365nm等长波长的光而被活化的高感度的光聚合引发剂。
本发明通过提供下述通式(I)所示的肟酯化合物以及以该肟酯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及R2各自独立地表示R11、OR11、COR11、SR11、CONR12R13或CN,
R11、R12及R13各自独立地表示氢原子、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,这些烷基、芳基、芳烷基及杂环基的氢原子还可以进一步被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、羧基或环氧基取代,R21、R22及R23各自独立地表示氢原子、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及R23所示的取代基的亚烷基部分的亚甲基还可以被不饱和键、醚键、硫醚键、酯键、硫酯键、酰胺键或氨酯键中断1~5次,上述取代基的烷基部分可以是分支侧链、还可以是环状烷基,上述取代基的烷基末端可以是不饱和键,另外R12和R13以及R22和R23还可以分别一起形成环。
R3及R4各自独立地表示R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11、CN、卤原子或羟基,a及b各自独立地为0~4。
X表示氧原子、硫原子、硒原子、CR31R32、CO、NR33或PR34,R31、R32、R33及R34各自独立地表示R11、OR11、COR11、SR11、CONR12R13或CN,
当X为CR31R32时,R3及R4可以一起形成环,或者R3可以借助-X-与相邻苯环的一个碳原子键合形成环结构;
当X为氧原子、硫原子、硒原子或PR34时,R3可以借助-X-与相邻苯环的一个碳原子键合形成环结构,或者R3和R4可以一起形成环,R31、R32、R33及R34可以各自独立地与相邻的任一苯环一起形成环。)
另外,本发明提供含有上述光聚合引发剂及具有烯属不饱和键的聚合性化合物而成的感光性组合物。
另外,本发明还提供含有上述光聚合引发剂及具有烯属不饱和键的碱性显影性化合物而成的碱性显影性感光性树脂组合物。
另外,本发明还提供在上述碱性显影性感光性树脂组合物中进一步含有着色剂而成的着色碱性显影性感光性树脂组合物。
具体实施方式
以下详细地说明本发明的肟酯化合物及以该化合物为有效成分的光聚合引发剂。
上述通式(I)中,作为R11、R12、R13、R21、R22、R23、R31、R32、R33及R34所表示的烷基,例如可举出甲基、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、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、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1~8的烷基。
作为R11、R12、R13、R21、R22、R23、R31、R32、R33及R34所示的芳基,例如可举出苯基、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及R34所示的芳烷基,例如可优选地举出苄基、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及R34所示的杂环基,例如可优选地举出吡啶基、嘧啶基、呋喃基、噻嗯基、四氢呋喃基、二氧杂戊环基等5~7元杂环。
另外,作为R12和R13可一起形成的环、R22和R23可一起形成的环、R3和R4可以一起形成的环、R3可以借助-X-与相邻苯环的一个碳原子键合形成的环结构以及R31、R32、R33可以与相邻苯环一起形成的环,例如可优选地举出环戊烷环、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,作为可取代R11、R12、R13、R21、R22、R23、R31、R32、R33及R34的卤原子,可举出氟、氯、溴、碘。另外,作为可取代R11、R12、R13、R21、R22、R23、R31、R32、R33及R34的杂环基,例如可举出吡啶基、嘧啶基、呋喃基、苯并噁唑-2-基、四氢吡喃基、吡咯烷基、咪唑啉基、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及R4所示的卤原子,可举出氟、氯、溴、碘。
上述R11、R12、R13、R21、R22及R23所示的取代基的亚烷基部分的亚甲基可以被不饱和键、醚键、硫醚键、酯键、硫酯键、酰胺键或氨酯键中断1~5次,此时中断的键合基团可以是1种,也可以是2种以上,在为可连续中断的基团的情况下,可以是2个以上连续地中断。
另外,上述取代基的烷基部分可以是分支侧链,也可以是环状烷基,上述取代基的烷基末端可以是不饱和键。
本发明的肟酯化合物中,上述通式(I)中的X为硫原子时,由于溶解性优异,因此优选。另外,由于溶解性优异,因此还优选上述通式(I)中R1及R2为下述基团:可以被选自卤原子、OR21及COR21的1种以上取代的碳原子数为1~20的烷基(可以是分支侧链,也可以为环状烷基);可以被选自卤原子、OR21及COR21的1种以上取代的碳原子数为6~30的芳基;或者可以被选自卤原子、OR21及COR21的1种以上取代的碳原子数为7~30的芳烷基。
其中,由于合成容易、感度也高,因此优选X为硫原子或者R1及R2为下述基团:可以被选自卤原子取代的碳原子数为1~20的烷基(可以是分支侧链,也可以为环状烷基);可被卤原子取代的碳原子数为6~30的芳基;或者可被卤原子取代的碳原子数为7~30的芳烷基。特别优选的例子可举出R1为甲基或十一烷基的肟酯化合物、R2为甲基或苯基的肟酯化合物。
因此,作为上述通式(I)所示的本发明的肟酯化合物的优选具体例子,可举出以下的化合物No.1~No.25的化合物,但本发明并不限于以下化合物。
上述通式(I)所示的本发明的肟酯化合物的合成方法并无特别限定,例如X为硫原子的肟酯化合物可以按照下述的反应式利用以下方法来制造。首先,在氢氧化钠的存在下使对氯硝基苯1与苯硫酚2反应,获得硫醚化合物3,接着在氯化铝的存在下使硫醚化合物3与酰氯4反应,获得酰基化合物5。接着使酰基化合物5与盐酸羟胺反应,获得肟化合物6。然后使肟化合物6与酸酐7或者酰氯7’反应,获得上述通式(I)中的X为硫原子的本发明的肟酯化合物。另外,X为氧原子、硒原子、碳原子、N-R5及P-R12的肟酯化合物也可按照上述方法制造。
本发明的肟酯化合物作为具有烯属不饱和键的聚合性化合物的光聚合引发剂有用。
接着,说明本发明的感光性组合物。
本发明的感光性组合物含有以上述本发明的肟酯化合物为有效成分的光聚合引发剂及具有烯属不饱和键的聚合性化合物、以及根据需要使用的无机填充剂和/或着色剂、以及溶剂等任意成分。
作为上述具有烯属不饱和键的聚合性化合物,并无特别限定,可以使用以往在感光性组合物中使用的物质,例如可举出乙烯、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、乙烯基乙酸、烯丙基乙酸、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、羟乙基(甲基)丙烯酸酯·马来酸酯、羟丙基(甲基)丙烯酸酯·马来酸酯、二环戊二烯·马来酸酯或具有1个羧基和2个以上(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.26~No.29、(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)丙烯酸烯丙基酯、(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与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、苯撑二甲基双(甲基)丙烯酰胺、α-氯丙烯酰胺、N-2-羟基乙基(甲基)丙烯酰胺等不饱和一元酸及多元胺的酰胺;丙烯醛等不饱和醛;(甲基)丙烯腈、α-氯丙烯腈、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基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;烯丙基醇、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、烯丙基缩水甘油基醚等乙烯基醚;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、氯戊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、聚硅氧烷等在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、邻苯二甲酸二烯丙基酯、磷酸三烯丙基酯、异氰脲酸三烯丙基酯、乙烯基硫醚、乙烯基咪唑、乙烯基噁唑啉、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及聚异氰酸酯化合物的乙烯基氨酯化合物、含羟基的乙烯基单体及聚环氧化合物的乙烯基环氧化合物等。其中,优选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个羧基与2个以上(甲基)丙烯酰基的多官能(甲基)丙烯酸酯、不饱和一元酸与多元醇或多元酚的酯中以本发明的肟酯化合物为有效成分的光聚合引发剂。
这些聚合性化合物可以单独使用或者混合2种以上使用,当混合2种以上使用时,还可预先将它们共聚制成共聚物后使用。
化合物No.26
化合物No.27
化合物No.28
化合物No.29
另外,作为上述具有烯属不饱和键的聚合性化合物,还可以使用具有烯属不饱和键的碱性显影性化合物,将本发明的感光性组合物制成碱性显影性感光性树脂组合物。作为该具有烯属不饱和键的碱性显影性化合物,可以使用丙烯酸酯的共聚物、苯酚及/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、通过使不饱和一元酸、进而使多元酸酐作用于下述通式(II)所示的环氧化合物等环氧化合物而获得的树脂。其中,优选通过使不饱和一元酸、进而使多元酸酐作用于下述通式(II)所示的环氧化合物等环氧化合物而获得的树脂。
另外,上述具有烯属不饱和键的碱性显影性化合物优选含有0.2~1.0当量的不饱和基团。
(式中,X1表示直接键合、亚甲基、碳原子数为1~4的亚烷基(alkylidene)、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30]或[化学式31]所示的取代基,该亚烷基可以被卤原子取代,R41、R42、R43及R44各自独立地表示氢原子、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、烷氧基及链烯基可以被卤原子取代,m为0~10的整数。)
[化学式30]
(式中,Y1表示氢原子、或者可被碳原子数为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、烷氧基及链烯基可被卤原子取代,d为0~5的数。)
[化学式31]
作为作用于上述环氧化合物的上述不饱和一元酸,可举出丙烯酸、甲基丙烯酸、巴豆酸、肉桂酸、山梨酸、羟乙基甲基丙烯酸酯·马来酸酯、羟乙基丙烯酸酯·马来酸酯、羟丙基甲基丙烯酸酯·马来酸酯、羟丙基丙烯酸酯·马来酸酯、二环戊二烯·马来酸酯等。
另外,作为在作用了上述不饱和一元酸后作用的上述多元酸酐,可举出联(二)邻苯二甲酸二酐、四氢邻苯二甲酸酐、琥珀酸酐、联苯四甲酸酐、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、乙二醇双脱水偏苯三酸酯、甘油三脱水偏苯三酸酯、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、上述不饱和一元酸及上述多元酸酐的反应摩尔比优选如下。即,在具有相对于上述环氧化合物的1个环氧基以0.1~1.0个加成上述不饱和一元酸的羧基而获得的结构的环氧加成物中,优选达到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个的比例。
上述环氧化合物、上述不饱和一元酸及上述多元酸酐的反应可以按照常规方法进行。
为了进行酸值调整以改良本发明的(着色)碱性显影性感光性树脂组合物的显影性,可以将上述具有烯属不饱和键的碱性显影性化合物与单官能或多官能环氧化合物并用。上述具有烯属不饱和键的碱性显影性化合物优选固态成分的酸值为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方式来进行选择。
作为上述单官能环氧化合物,可举出甲基丙烯酸缩水甘油酯、甲基缩水甘油基醚、乙基缩水甘油基醚、丙基缩水甘油基醚、异丙基缩水甘油基醚、丁基缩水甘油基醚、异丁基缩水甘油基醚、叔丁基缩水甘油基醚、戊基缩水甘油基醚、己基缩水甘油基醚、庚基缩水甘油基醚、辛基缩水甘油基醚、壬基缩水甘油基醚、癸基缩水甘油基醚、十一烷基缩水甘油基醚、十二烷基缩水甘油基醚、十三烷基缩水甘油基醚、十四烷基缩水甘油基醚、十五烷基缩水甘油基醚、十六烷基缩水甘油基醚、2-乙基己基缩水甘油基醚、烯丙基缩水甘油基醚、炔丙基缩水甘油基醚、p-甲氧基乙基缩水甘油基醚、苯基缩水甘油基醚、p-甲氧基缩水甘油基醚、p-丁基苯酚缩水甘油基醚、甲苯基缩水甘油基醚、2-甲基甲苯基缩水甘油基醚、4-壬基苯基缩水甘油基醚、苄基缩水甘油基醚、p-枯烯基苯基缩水甘油基醚、三苯甲基缩水甘油基醚、甲基丙烯酸2,3-环氧基丙酯、环氧化大豆油、环氧化亚麻仁油、丁酸缩水甘油酯、乙烯基环己烷单氧化物、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.30、No.31等。
化合物No.30
化合物No.31
作为上述多官能环氧化合物,当使用选自双酚型环氧化合物及缩水甘油基醚类中的一种以上时,由于能够获得特性更为良好的(着色)碱性显影性感光性树脂组合物,因此优选。作为该双酚型环氧化合物,除了可以使用上述通式(II)所示的环氧化合物之外,例如还可以使用氢化双酚型环氧化合物等双酚型环氧化合物。另外,作为该缩水甘油基醚类,可举出乙二醇二缩水甘油基醚、丙二醇二缩水甘油基醚、1,4-丁二醇二缩水甘油基醚、1,6-己二醇二缩水甘油基醚、1,8-辛二醇二缩水甘油基醚、1,10-癸二醇二缩水甘油基醚、2,2-二甲基-1,3-丙二醇二缩水甘油基醚、二乙二醇二缩水甘油基醚、三乙二醇二缩水甘油基醚、四乙二醇二缩水甘油基醚、六乙二醇二缩水甘油基醚、1,4-环己烷二甲醇二缩水甘油基醚、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)甲烷等。
另外,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、四氢邻苯二甲酸二缩水甘油酯、二聚物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;二环戊二烯二氧化物等二氧化物化合物;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。
本发明的感光性组合物中,光聚合引发剂的添加量并无特别限定,但本发明的肟酯化合物的添加量相对于具有烯属不饱和键的上述聚合性化合物100质量份优选为1~70质量份、更优选为1~50质量份、最优选为5~30质量份。
特别是将本发明的感光性组合物制成(着色)碱性显影性感光性树脂组合物时,上述具有烯属不饱和键的碱性显影性化合物的含量在本发明的(着色)碱性显影型感光性树脂组合物中优选为1~20质量%、特别优选为3~12质量%。
本发明的感光性组合物中可以进一步加入溶剂。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及具有烯属不饱和键的聚合性化合物等)的溶剂,例如可举出甲乙酮、甲基戊基酮、二乙基酮、丙酮、甲基异丙基酮、甲基异丁基酮、环己酮等酮类;乙基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲基醚等醚系溶剂;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;乙二醇单甲基醚、乙二醇单乙基醚、丙二醇单甲基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、Swasol#310(COSMO松山石油株式会社)、Solvesso#100(EXXON化学株式会社)等石蜡系溶剂;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、三乙基胺、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、二甲基亚砜、水等,这些溶剂可单独使用1种,或者作为2种以上的混合溶剂使用。
其中,优选酮类、溶纤剂系溶剂等,特别优选丙二醇-1-单甲基醚-2-乙酸酯、环己酮等,其原因在于在感光性组合物中抗蚀剂与光聚合引发剂的相容性良好。
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,例如可举出氧化镍、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,无机化合物的含量相对于具有烯属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。
这些无机化合物例如可作为填充剂、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、疏油墨剂等使用。
另外,本发明的感光性组合物(特别是碱性显影性感光性树脂组合物)还可以进一步含有着色剂来制成着色感光性组合物。作为该着色剂,可举出颜料、染料、天然色素等。这些着色剂可单独使用或者混合2种以上使用。
作为上述颜料,例如可举出亚硝基化合物、硝基化合物、偶氮化合物、二偶氮化合物、呫吨化合物、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、紫环酮化合物、苝化合物、二酮吡咯并吡咯化合物、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、菁染料的金属配位化合物;色淀颜料;通过炉黑法、槽法、热裂法获得的炭黑、或者乙炔黑、科琴黑或灯黑等炭黑;对上述炭黑进行了酸性或碱性表面处理后的物质;石墨、石墨化炭黑、活性炭、碳纤维、碳纳米管、碳微螺旋、碳纳米角、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、普鲁士蓝、佛青、赛璐里安蓝、维利迪安颜料、翡翠绿、硫酸铅、铅黄、锌黄、氧化铁红(红色氧化铁(III))、镉红、合成铁黑、琥珀色等有机或无机颜料。这些颜料可单独使用或者混合多个使用。
上述颜料还可以使用市售的颜料,例如可举出颜料红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,可举出偶氮染料、蒽醌染料、靛类染料、三芳基甲烷染料、呫吨染料、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,这些染料可以混合多个使用。
本发明的感光性组合物中,上述着色剂的添加量相对于具有烯属不饱和键的上述聚合性化合物100质量份优选为50~350质量份、更优选为100~250质量份。
另外,通过与具有烯属不饱和键的上述聚合性化合物一起使用其他的有机聚合物,还可以改善固化物的特性。作为该有机聚合物,例如可举出聚苯乙烯、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、苯氧树脂、聚酰胺酰亚胺树脂、聚氨基酸树脂、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。
使用其它的有机聚合物时,其使用量相对于具有烯属不饱和键的上述聚合性化合物100质量份优选为10~500质量份。
本发明的感光性组合物中还可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二缩水甘油基醚(甲基)丙烯酸酯、双酚F二缩水甘油基醚(甲基)丙烯酸酯、双酚Z二缩水甘油基醚(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,可举出巯基乙酸、硫代苹果酸、硫代水扬酸、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-甲基硫代)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-巯基乙基胺、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获得的二硫化物、碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸、3-碘丙磺酸等碘代烷基化合物。
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,这些物质还可组合使用。
另外,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之外,还可根据需要并用其它的光聚合引发剂或增感剂,通过并用其它的光聚合引发剂,有时还可发挥显著的协同效果。
作为能够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,例如可举出二苯甲酮、苯基联苯基酮、1-羟基-1-苯甲酰基环己烷、苯偶姻、苄基二甲基缩酮、1-苄基-1-二甲基氨基-1-(4’-吗啉代苯甲酰基)丙烷、2-吗啉基-2-(4’-甲基巯基)苯甲酰基丙烷、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-苯甲酰基-4’-甲基二苯基硫化物、苯偶姻丁基醚、2-羟基-2-苯甲酰基丙烷、2-羟基-2-(4’-异丙基)苯甲酰基丙烷、4-丁基苯甲酰基三氯甲烷、4-苯氧基苯甲酰基二氯甲烷、苯甲酰基甲酸甲酯、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’-联二咪唑、4,4-偶氮二异丁腈、三苯基膦、樟脑醌、N-1414、N-1717、N-1919、PZ-408(艾迪科株式会社制)、IRGACURE369、IRGACURE907、IRGACUREOXE01、IRGACUREOXE02(Ciba Specialty Chemicals株式会社社制)、苯甲酰过氧化物、下述通式(III)~(V)所示的化合物等,这些光聚合引发剂可以使用1种或者组合2种以上使用。使用这些其他的光聚合引发剂时,其使用量优选为本发明的肟酯化合物的使用量的等量以下。
(式中、R1及R2与上述通式(I)中的定义相同,R6与R1相同,Y2表示卤原子或烷基,n为0~5。)
(式中,R1及R2与上述通式(I)中的定义相同,T6、Y2及n与上述通式(III)中的定义相同,R’1、R’2及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及R2与上述通式(I)中的定义相同,R6、Y2及n与上述通式(III)中的定义相同,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。)
另外,本发明的感光性组合物中还可根据需要添加对苯甲醚、氢醌、邻苯二酚、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;表面调节剂;抗氧化剂;紫外线吸收剂;分散辅助剂;防凝集剂;催化剂;效果促进剂;增感剂;交联剂;增粘剂等常用的添加剂。
本发明的感光性组合物中,除具有烯属不饱和键的上述聚合性化合物及本发明的肟酯化合物以外的任意成分(不包括上述其它的光聚合引发剂、无机填充剂、着色剂及溶剂)的使用量根据其使用目的适当选择,并无特别限定,优选相对于具有烯属不饱和键的上述聚合性化合物100质量份总计为50质量份以下。
本发明的感光性组合物可以通过旋涂、辊涂、棒涂、模涂、淋涂、各种印刷、浸渍等公知的方法适用于钠玻璃、石英玻璃、半导体基板、金属、纸、塑料等支撑基体上。另外,也可以暂时施加于薄膜等支撑基体上之后转印至其它的支撑基体上,其适用方法并无限定。
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、打印基板、或彩色电视机、PC监视器、便携信息末端、数码相机等彩色显示的液晶显示元件中的滤色器、等离子显示面板用的电极材料、粉末涂料、印刷油墨、印刷版、粘接剂、齿科用组合物、凝胶涂层、电子工学用的光致抗蚀剂、电镀抗蚀剂、蚀刻抗蚀剂、液状及干燥膜两者、焊锡抗蚀剂、用于制造各种显示用途用的滤色器的物质或者等离子显示面板、电发光显示装置及LCD制造工序中用于形成结构的抗蚀剂、用于封入电及电子部件的组合物、磁记录材料、微小机械零件、波导、光开关、镀覆用掩模、蚀刻掩模、彩色试验体系、玻璃纤维电缆涂布、丝网印刷用模板、用于通过立体平版印刷来制造三维物体的材料、全息照相记录用材料、图像记录材料、微细电子回路、脱色材料、用于图像记录材料的脱色材料、使用微胶囊的图像记录材料用的脱色材料、印刷配线板用光致抗蚀剂材料、UV及可见激光直接图像体系用的光致抗蚀剂材料、印刷电路基板的依次层叠中用于形成电介质层的光致抗蚀剂材料或者保护膜等各种用途中,其用途并无特别限定。
另外,作为使含有本发明的肟酯化合物的感光性组合物固化时所使用的活性光的光源,可以使用发出波长300~450nm的光的光源,例如可以使用超高压汞、水银蒸气弧、碳弧、氙弧等。
实施例
以下举出实施例等更加详细地说明本发明,但本发明并不限定于这些实施例。
〔实施例1-1〕化合物No.1的制造
<步骤1>硫醚化合物的制造
在氮气氛下加入对氯硝基苯15.8g(100mmol)、苯硫酚12.1g(110mmol)及二甲基乙酰胺69.4g,加入氢氧化钠12.5g(150mmol)并在50℃下搅拌1小时。冷却至室温,利用乙酸乙酯/水系进行油水分离。蒸馏除去溶剂,以黄色晶体的形式获得目标物硫醚化合物23.1g(收率为99%、HPLC纯度为99%)。
<步骤2>酰基体的制造
在氮气氛下加入氯化铝12.0g(90mmol)及二氯乙烷27.0g,在冰冷下慢慢滴加乙酰氯3.56g(45mmol)、接着慢慢滴加步骤1中获得的硫醚化合物5.78g(25mmol)及二氯乙烷27.0g,在5℃下搅拌30分钟。将反应液倒入冰水中进行油水分离。经过脱溶剂、从乙酸乙酯重结晶,以淡黄色晶体的形式获得目标物酰基体2.94g(收率为43%、HPLC纯度为96%)。
<步骤3>化合物No.1的制造
在氮气流下加入步骤2中获得的酰基体2.73g(10mmol)、盐酸羟胺1.04g(15mmol)、及二甲基乙酰胺5.8g,在80℃下搅拌1小时。冷却至室温后进行油水分离。蒸馏除去溶剂,在残留物中加入乙酸丁酯10.0g、接着加入乙酸酐1.23g(12mmol),在90℃下搅拌1小时,冷却至室温。利用5%氢氧化钠水溶液进行中和,经过油水分离、脱溶剂、从乙酸乙酯重结晶,获得淡黄色晶体2.41g(收率为73%、HPLC纯度为99%)。对该淡黄色晶体进行各种分析,结果确认该淡黄色晶体为目标物的化合物No.1。分析结果如下所示。
(分析结果)
(1)熔点:91.9℃
(2)1H-NMR测定:(ppm)
2.29(s:3H)、2.42(s:3H)、7.28(d:2H)、7.53(d:2H)、7.81(d:2H)、8.10(d:2H)
(3)IR测定:(cm-1)
1775、1592、1576、1519、1477、1393、1368、1342、1316、1203、1115、1085、1009、993、939、902、853、846、836、741、682、639
(4)UV光谱测定(氯仿)
λmax=346nm
(5)分解温度测定(氮气气氛下、升温速度为10℃/分钟、5%质量减少温度)
270℃
〔实施例1-2〕化合物No.23的制造
除了将实施例1-1的步骤2中使用的乙酰氯替换成十二烷酰氯之外,全部按照与实施例1-1相同的顺序制造化合物No.23。作为中间体的酰基体的收率为30%、HPLC纯度为99%。所得化合物No.23的收率为66%、HPLC纯度为99%。所得化合物No.23的分析结果如下所示。
(1)熔点:73.9℃
(2)1H-NMR测定:(ppm)
0.88(t:3H)、1.20~1.49(m:16H)、1.58(tt:2H)、2.28(s:3H)、2.86(t:2H)、7.25(d:2H)、7.54(d:2H)、7.77(d:2H)、8.10(d:2H)
(3)IR测定:(cm-1)
3095、2917、2851、1766、1598、1517、1471、1397、1365、1348、1284、1204、1083、1000、946、895、853、837、745、720、686
(4)UV光谱测定(氯仿)
λmax=341nm
(5)分解温度测定(氮气气氛下、升温速度为10℃/分钟、5%质量減少温度)
255℃
〔实施例1-3〕化合物No.24的制造
除了将实施例1-1的步骤2中使用的乙酰氯替换成十二烷酰氯、将实施例1-1的步骤3中使用的乙酸酐替换成苯甲酰氯及三乙基胺之外,全部按照与实施例1-1相同的顺序制造化合物No.24。作为中间体的酰基体的收率为30%、HPLC纯度为99%。所得化合物No.24的收率为64%、HPLC纯度为99%。所得化合物No.24的分析结果如下所示。
(1)熔点:92.0℃
(2)1H-NMR测定:(ppm)
0.87(t:3H)、1.20~1.49(m:16H)、1.69(tt:2H)、2.99(t:2H)、7.27(ddd:2H)、7.52(dd:2H)、7.57(ddd:2H)、7.64(tt:1H)、7.86(ddd:2H)、8.11(ddd:2H)、8.13(d:2H)
(3)IR测定:(cm-1)
2952、2918、2849、1749、1593、1575、1509、1470、1449、1340、1243、1177、1110、1082、1065、1022、919、884、846、784、744、722、707、680
(4)UV光谱测定(氯仿)
λmax=341nm
(5)分解温度测定(氮气气氛下、升温速度为10℃/分钟、5%质量減少温度)
245℃
〔实施例2〕感光性组合物No.1的制备
在丙烯酸系共聚物14.0g中加入三羟甲基丙烷三丙烯酸酯5.90g、2.70g实施例1-1中所得的化合物No.1及乙基溶纤剂79.0g,充分搅拌,获得感光性组合物No.1。
上述丙烯酸系共聚物如下获得:将甲基丙烯酸20质量份、甲基丙烯酸羟基乙酯15质量份、甲基丙烯酸甲酯10质量份及甲基丙烯酸丁酯55质量份溶解在乙基溶纤剂300质量份中,在氮气氛下加入偶氮二异丁腈0.75质量份,在70℃反应5小时,从而获得。
〔实施例3-1~3-3〕感光性组合物No.2-1~No.2-3的制备
混合二季戊四醇五丙烯酸酯15.0g、1,4-丁二醇二缩水甘油基醚3.74g,添加实施例1-1~1-3中获得的化合物No.1、化合物No.23及化合物No.24的任一者3.30g、以及乙基溶纤剂78g,充分搅拌,分别获得感光性组合物No.2-1~2-3。
〔实施例4-1~4-3〕作为碱性显影性感光性树脂组合物的感光性组合物No.3-1~No.3-3的制备
<步骤1>碱性显影性树脂组合物No.1的制备
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及丙二醇-1-单甲基醚-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-单甲基醚-2-乙酸酯7.18g、琥珀酸酐4.82g及四丁基乙酸铵0.25g,在100℃下搅拌5小时。然后,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及丙二醇-1-单甲基醚-2-乙酸酯2.18g,在120℃下搅拌12小时、80℃下搅拌2小时、40℃下搅拌2小时后,加入丙二醇-1-单甲基醚-2-乙酸酯13.1g,以丙二醇-1-单甲基醚-2-乙酸酯溶液的形式获得目标物碱性显影性树脂组合物No.1(Mw=4200、Mn=2100、酸值(固态成分)为55mgKOH/g)。
<步骤2>感光性组合物No.3-1~No.3-3的制备
混合2.68g步骤1中获得的碱性显影性树脂组合物No.1、三羟甲基丙烷三丙烯酸酯0.73g、丙二醇-1-单甲基醚-2-乙酸酯7.91g及环己酮5.18g,添加实施例1-1~1-3中获得的化合物No.1、化合物No.23及化合物No.24的任一者1.58g,充分搅拌,分别获得作为碱性显影性感光性树脂组合物的感光性组合物No.3-1~3-3。
〔实施例5〕作为碱性显影性感光性树脂组合物的感光性组合物No.4的制备
<步骤1>碱性显影性树脂组合物No.2的制备
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及丙二醇-1-单甲基醚-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-单甲基醚-2-乙酸酯35.0g、联苯四甲酸酐59.0g及四正丁基溴化铵0.24g,在120℃下搅拌4小时。然后加入四氢邻苯二甲酸酐20g,在120℃下搅拌4小时、100℃下搅拌3小时、80℃下搅拌4小时、60℃下搅拌6小时、40℃下搅拌11小时之后,加入丙二醇-1-单甲基醚-2-乙酸酯90.0g,以丙二醇-1-单甲基醚-2-乙酸酯溶液的形式获得目标物碱性显影性树脂组合物No.2(Mw=5000、Mn=2100、酸值(固态成分)为92.7mgKOH/g)。
<步骤2>感光性组合物No.4的制备
混合2.68g步骤1中获得的碱性显影性树脂组合物No.2、三羟甲基丙烷三丙烯酸酯0.73g、丙二醇-1-单甲基醚-2-乙酸酯7.91g及环己酮5.18g,添加实施例1-1中获得的化合物No.1的1.58g并充分搅拌,获得作为碱性显影性感光性树脂组合物的感光性组合物No.4。
〔实施例6〕作为着色碱性显影性感光性树脂组合物的感光性组合物No.5的制备
除了还进一步加入2.00g颜料蓝15之外,与实施例4-1~4-3同样地获得作为着色碱性显影性感光性树脂组合物的感光性组合物No.5-1~5-3。
〔实施例7〕作为着色碱性显影性感光性树脂组合物的感光性组合物No.6的制备
除了还进一步加入炭黑3.00g之外,与实施例5同样地获得作为着色碱性显影性感光性树脂组合物的感光性组合物No.6。
〔比较例1〕感光性组合物No.7的制备
除了使用3.30g下述所示的比较化合物1来代替3.30g实施例1-1中获得的化合物No.1之外,与实施例3-1同样地获得比较用的感光性组合物No.7。
〔比较例2〕感光性组合物No.8的制备
除了使用1.58g下述所示的比较化合物2来代替3.30g实施例1-1中获得的化合物No.1之外,与实施例3-1同样地获得比较用的感光性组合物No.8。
比较化合物2
〔比较例3〕作为碱性显影性感光性树脂组合物的感光性组合物No.9的制备
除了使用1.58g比较化合物1来代替1.58g实施例1-1中获得的化合物No.1之外,与实施例4-1同样地获得比较用的作为碱性显影性感光性树脂组合物的感光性组合物No.9。
〔比较例4〕作为碱性显影性感光性树脂组合物的感光性组合物No.10的制备
除了使用1.58g比较化合物2来代替1.58g实施例1-1中获得的化合物No.1之外,与实施例4-1同样地获得比较用的作为碱性显影性感光性树脂组合物的感光性组合物No.10。
〔实施例8〕感光性组合物No.11的制备
除了还进一步加入氧化钛4.52g之外,与实施例2同样地获得感光性组合物No.11。
对所得感光性组合物No.2-1~No.2-3及比较用的感光性组合物No.7、No.8如下进行硬度试验。试验结果示于表1。
另外,对作为碱性显影性感光性树脂组合物的感光性组合物No.3-1~No.3-3及比较用的感光性组合物No.9、No.10如下进行感度的评价。评价结果示于表2。
<硬度试验>
利用#3的棒涂器将感光性组合物涂布在厚度为50μm的聚对苯二甲酸乙二醇薄膜上。使用带有带式传送机的光照射装置对其照射80W/cm的高压汞灯的光以使其固化。从灯至带式传送机的距离为10cm、带式传送机的线速度为8cm/分钟。固化后室温放置24小时,然后使用铅笔硬度试验机以1kg的负荷测定铅笔硬度。
<感度>
使用#3棒涂器将碱性显影性感光性树脂组合物以约1μm的厚度涂布在铝基板上。在60℃下进行预烘焙15分钟后,通过日本分光株式会社制的分光照射装置CT-25CP,使用超高压汞灯作为光源来进行曝光,接着在25℃下浸渍于2.5质量%碳酸钠溶液中进行显影,充分水洗,分别测定365nm及405nm下的分光感度。感度如下评价:通过残留于铝基板上的固化膜段数和365nm及405nm各自的射出光量,求出在365nm及405nm的各个光下固化所需要的最小固化能量。
表1
感光性组合物 | 试验化合物 | 铅笔硬度 |
No.2-1(实施例3-1) | 化合物No.1 | 3H |
No.2-2(实施例3-2) | 化合物No.23 | 3H |
No.2-3(实施例3-3) | 化合物No.24 | 3H |
No.7(比较例1) | 比较化合物1 | 1H |
No.8(比较例2) | 比较化合物2 | 2H |
表2
由表1可知,实施例3-1~3-3的感光性组合物No.2-1~No.2-3的硬度较高,而比较例1的感光性组合物No.7及比较例2的感光性组合物No.8不具有充分的硬度。
另外,由表2可知,作为碱性显影性感光性树脂组合物的实施例4-1~4-3的感光性组合物No.3-1~No.3-3对于长波长的365nm及405nm的任一光的感度均优异。与此相对,比较例3的感光性组合物No.9对于365nm的光的感度很低,因此不得不增大曝光量,而对于405nm的光并未发生固化。另外,比较例4的感光性组合物No.10对于365nm的光具有充分的感度,但对于405nm的光的感度很低,因此不得不增大曝光量。
本发明的肟酯化合物的感光性优异,特别是对于长波长的365nm(i线)及405nm(h线)的辉线的感度优异,因此作为光聚合引发剂是有用的。
Claims (6)
2.一种光聚合引发剂,其以权利要求1所述的肟酯化合物为有效成分。
3.一种感光性组合物,其是含有权利要求2所述的光聚合引发剂及具有烯属不饱和键的聚合性化合物而成的。
4.根据权利要求3所述的感光性组合物,其还进一步含有无机化合物,该无机化合物选自氧化镍、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;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。
5.一种碱性显影性感光性树脂组合物,其是含有权利要求2所述的光聚合引发剂及具有烯属不饱和键的碱性显影性化合物而成的。
6.一种着色碱性显影性感光性树脂组合物,其是在权利要求5所述的碱性显影性感光性树脂组合物中进一步含有着色剂而成的。
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