WO2003072614A2 - Thiol compound, photopolymerization initiator composition and photosensitive composition - Google Patents
Thiol compound, photopolymerization initiator composition and photosensitive composition Download PDFInfo
- Publication number
- WO2003072614A2 WO2003072614A2 PCT/JP2003/002219 JP0302219W WO03072614A2 WO 2003072614 A2 WO2003072614 A2 WO 2003072614A2 JP 0302219 W JP0302219 W JP 0302219W WO 03072614 A2 WO03072614 A2 WO 03072614A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- photopolymerization initiator
- thiol compound
- compound
- composition
- Prior art date
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- -1 Thiol compound Chemical class 0.000 title claims abstract description 147
- 239000000203 mixture Substances 0.000 title claims abstract description 141
- 239000003999 initiator Substances 0.000 title claims abstract description 86
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 61
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 37
- TXJZAWRTHMZECY-UHFFFAOYSA-N 2-(3-sulfanylbutanoyloxy)ethyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCOC(=O)CC(C)S TXJZAWRTHMZECY-UHFFFAOYSA-N 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- WQECNJBUYKDLGS-UHFFFAOYSA-N 2-(2-methyl-2-sulfanylpropanoyl)oxyethyl 2-methyl-2-sulfanylpropanoate Chemical compound CC(C)(S)C(=O)OCCOC(=O)C(C)(C)S WQECNJBUYKDLGS-UHFFFAOYSA-N 0.000 claims description 20
- HFGWEGUVPBZOEA-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyl-2-sulfanylpropanoic acid Chemical compound CC(C)(S)C(O)=O.CC(C)(S)C(O)=O.CC(C)(S)C(O)=O.CCC(CO)(CO)CO HFGWEGUVPBZOEA-UHFFFAOYSA-N 0.000 claims description 20
- WBEKRAXYEBAHQF-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O.CC(S)CC(O)=O.CC(S)CC(O)=O.CCC(CO)(CO)CO WBEKRAXYEBAHQF-UHFFFAOYSA-N 0.000 claims description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 18
- 239000000049 pigment Substances 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- ZUWFDHPIBGDTSU-UHFFFAOYSA-N 2-(2-methyl-2-sulfanylpropanoyl)oxypropyl 2-methyl-2-sulfanylpropanoate Chemical compound CC(S)(C)C(=O)OC(C)COC(=O)C(C)(C)S ZUWFDHPIBGDTSU-UHFFFAOYSA-N 0.000 claims description 9
- 229960004063 propylene glycol Drugs 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 229940083957 1,2-butanediol Drugs 0.000 claims description 7
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- 229940093476 ethylene glycol Drugs 0.000 claims description 5
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 4
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- UJCUIGVRXJDWNI-UHFFFAOYSA-N propane-1,2-diol;3-sulfanylbutanoic acid Chemical compound CC(O)CO.CC(S)CC(O)=O UJCUIGVRXJDWNI-UHFFFAOYSA-N 0.000 claims description 4
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 abstract description 15
- 238000003860 storage Methods 0.000 abstract description 14
- 230000009467 reduction Effects 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 22
- 239000000126 substance Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 238000004949 mass spectrometry Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- JTMBCYAUSCBSEY-UHFFFAOYSA-N 2-methyl-2-sulfanylpropanoic acid Chemical compound CC(C)(S)C(O)=O JTMBCYAUSCBSEY-UHFFFAOYSA-N 0.000 description 6
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 239000012156 elution solvent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- KQBUONNTLMDRIE-UHFFFAOYSA-N 2-(3-sulfanylbutanoyloxy)propyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(C)OC(=O)CC(C)S KQBUONNTLMDRIE-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 description 3
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 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
- 238000000034 method Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 230000007261 regionalization Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- ZOMLUNRKXJYKPD-UHFFFAOYSA-N 1,3,3-trimethyl-2-[2-(2-methylindol-3-ylidene)ethylidene]indole;hydrochloride Chemical compound [Cl-].C1=CC=C2C(C)(C)C(/C=C/C=3C4=CC=CC=C4NC=3C)=[N+](C)C2=C1 ZOMLUNRKXJYKPD-UHFFFAOYSA-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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 2
- VKGGNKFWLIUWRV-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-bis(3-methoxyphenyl)imidazol-2-yl]-4,5-bis(3-methoxyphenyl)imidazole Chemical compound COC1=CC=CC(C=2C(=NC(N=2)(C=2C(=CC=CC=2)Cl)N2C(=C(N=C2C=2C(=CC=CC=2)Cl)C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 VKGGNKFWLIUWRV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 2
- PTPQZNNAUUSACC-UHFFFAOYSA-N 3-sulfanylpentanoic acid Chemical compound CCC(S)CC(O)=O PTPQZNNAUUSACC-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- NEAFWRKPYYJETG-UHFFFAOYSA-N 4-sulfanylpentanoic acid Chemical compound CC(S)CCC(O)=O NEAFWRKPYYJETG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavine T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- GZBUMTPCIKCWFW-UHFFFAOYSA-N triethylcholine Chemical compound CC[N+](CC)(CC)CCO GZBUMTPCIKCWFW-UHFFFAOYSA-N 0.000 description 1
- 229940113165 trimethylolpropane Drugs 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C323/51—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 atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—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 atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/0275—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with dithiol or polysulfide compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F3/00—Colour separation; Correction of tonal value
- G03F3/10—Checking the colour or tonal value of separation negatives or positives
- G03F3/106—Checking the colour or tonal value of separation negatives or positives using non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, other than silicon containing compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/117—Free radical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/127—Spectral sensitizer containing
Definitions
- the present invention relates to a novel thiol compound, to a photopolymerization initiator composition containing the thiol compound having high sensitivity and excellent storage stability, and to a photosensitive composition containing the photopolymerization initiator composition.
- Thiol compounds such as trimethylolpropane tris(3- mercaptopropionate) and pentaerythritol tetrakis (3- mercaptopropionate) are used widely in various applications in every kind of industrial field. Among them, the most general one is use of them for photosensitive compositions.
- Photosensitive compositions are used in various fields including many fields such as printing plates, color proofs, color filters, solder resists, and photocuring ink.
- room temperature, fast-curing and solventlessness which are the most characteristic properties of photocuring, have received attention in various fields including these applications from the viewpoints of environmental pollution, energy saving, safety in working, production costs and the like and many studies and developments have been made on photosensitive compositions.
- studies on pigment dispersion type resist for color filters have been under way for the purpose of increasing productivity and achieving high precision.
- color proofs and printing plates development has been under way for the purpose of achieving high speed and high precision in plate making.
- solder resists for printed boards have been studied.
- Photosensitive compositions are mainly composed of a photopolymerization initiator composition, a compound having an ethylenically unsaturated bond which cures by a polymerization reaction and various kinds of additives, and the kinds of the components depend on use to which the photosensitive composition is applied.
- the photopolymerization initiator composition is meant a composition containing at least one compound which participates in the initiation reaction of photopolymerization, such as a compound that generates a radical, an anion, or a cation by light, a compound having a chain transfer action, or a compound having sensitization activity.
- the compounds which constitute the photopolymerization initiator composition are selected by their photosensitive wavelengths and polymerization initiating properties.
- the compound having an ethylenically unsaturated bond and the additives are selected by polymerizability and physical properties of a desired cured product. They are combined and used as a photosensitive composition.
- Laid-open No. Hei 10-253815 discloses a photopolymerizable composition containing a polyfunctional thiol and an initiator selected from a group consisting of a biimidazole compound, a titanocene compound, a triazine compound and an oxazole compound.
- Japanese Patent Application Laid-open No. 2000-249822 (EP 1031579A2, US Patent No .6,455,207) discloses a photopolymerization initiator containing a sensitizer, an organic boron complex and a compound having a mercapto group.
- the attempt of achieving high sensitivity by use of such a polyfunctional thiol compound causes a problem of costing the storage stability.
- the inventors of the present invention have found that in order to obtain a photosensitive composition which has high sensitivity and excellent photocurability as well as excellent storage stability, selection of a photopolymerization initiator composition is important; in particular, selection of a thiol compound used as one component of the photopolymerization initiator composition is important.
- an object of the present invention is to provide a photopolymerization initiator composition having high sensitivity and excellent storage stability, a photosensitive composition containing the photopolymerization initiator composition, and a novel thiol compound suitable for the photopolymerization initiator composition.
- the inventors of the present invention have found that the above-mentioned problems are solved by using a thiol compound having a structure in which carbon atom(s) at the ⁇ - and/or ⁇ -position with respect to the mercapto group have a substituent as one component of the photopolymerization initiator composition to be contained in a photosensitive composition, thereby achieving the present invention.
- polyfunctional thiols disclosed or used in the above-mentioned publications are all those whose carbon chain bonded to the mercapto group is a straight chain but those whose carbon chain have a branched structure as referred to in the present invention are not disclosed.
- the present invention relates to the following photopolymerization initiator compositions, to the following novel thiol compounds suitable for the composition, and to the following photosensitive compositions.
- a photopolymerization initiator composition comprising a thiol compound having a mercapto group- containing group that has at least one substituent on carbon atom(s) at the ⁇ - and/or ⁇ -position to the mercapto group and a photopolymerization initiator.
- R 1 and R 2 represent each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that at least one of R 1 and R 2 is an alkyl group, m is 0 or an integer of 1 to 2, and n is 0 or 1.
- the alkylene glycol is ethylene glycol, 1, 2-propylene glycol or 1, 2-butanediol .
- the thiol compound is a compound represented by formula (A)
- R 3 to R 6 represent each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and L is a group represented by formula (1)
- R 1 , R 2 , m and n have the same meanings as defined in 5 above .
- R 1 , R 2 , m and n have the same meanings as defined in 5 above .
- thiol compound having a mercapto group-containing group is a compound selected from ethylene glycol bis (3-mercaptobutyrate) , 1, 2-propylene glycol (3-mercaptobutyrate), trimethylolpropane tris(3- mercaptobutyrate) , ethylene glycol bis (2- mercaptoisobutyrate) , 1, 2-propylene glycol bis (2- mercaptoisobutyrate) , and trimethylolpropane tris(2- mercaptoisobutyrate) .
- photopolymerization initiator composition as described in 1 above, wherein the photopolymerization initiator is at least one photopolymerization initiator selected from a group consisting of ⁇ -hydroxyacetophenones, ⁇ -aminoacetophenones, and biimidazoles .
- composition as described in 1 above, wherein the composition further comprises a sensitizer.
- the photosensitive composition as described in 17 above wherein the composition contains a polymer compound and/or a compound having an ethylenically unsaturated bond. 19. The photosensitive composition as described in 18 above, wherein the polymer compound is soluble in a solvent or an aqueous alkali solution.
- a thiol compound which is an ester compound derived from a mercapto group-containing carboxylic acid represented by formula (2) and a polyfunctional alcohol
- R ⁇ wherein R 1 and R 2 represent each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that at least one of R 1 and R 2 is an alkyl group, m is 0 or an integer of 1 to 2, and n is 0 or 1. 22.
- R 3 to R 6 represent each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and L is a group represented by formula (1)
- R 1 , R 2 , m and n have the same meanings as defined in 21 above.
- L is a group represented by formula ( 1 )
- R 1 , R 2 , m and n have the same meanings as defined in 21 above.
- Fig. 1 and Fig.2 are diagrams showing a 1 H-NMR spectrum and 13 C-NMR spectrum of ethylene glycol bis (3- mercaptobutyrate) (EGMB) ;
- Fig. 3 and Fig. 4 are diagrams showing a X H-NMR spectrum and 13 C -NMR spectrum of 1, 2-propylene glycol bis (3- mercaptobutyrate) (PGMB) ;
- Fig.5 and Fig. 6 are diagrams showing a ⁇ "H-NMR spectrum and 13 C -NMR spectrum of trimethylolpropane tris (3- mercaptobutyrate) (TPMB) ;
- Fig.7 and Fig. 8 are diagrams showing a ⁇ I- MR spectrum and 13 C -NMR spectrum of ethylene glycol bis (2- mercaptoisobutyrate) (EGMIB) ;
- Fig.9 and Fig.10 are diagrams showing a ⁇ -NMR spectrum and 13 C -NMR spectrum of 1, 2-propylene glycol bis (2- mercaptoisobutyrate) (PGMIB) ; and
- Fig. 11 and Fig. 12 are diagrams showing a 1 H-NMR spectrum and 13 C -NMR spectrum of trimethylolpropane tris (2-mercaptoisobutyrate) (TPMIB) .
- TPMIB trimethylolpropane tris (2-mercaptoisobutyrate)
- the thiol compound of the present invention is a thiol compound having a specific mercapto group-containing group, characterized in that the mercapto group-containing group is of a structure having at least one substituent on carbon atom(s) at the ⁇ - and/or ⁇ -position with respect to the mercapto group. It is preferred that at least one of the substituents be an alkyl group.
- the structure in which carbon atom(s) at the ⁇ - and/or ⁇ -position with respect to the mercapto group have a substituent means a structure having a branching at the carbon atoms at the ⁇ - and/or ⁇ -position with respect to the mercapto group, in other words, a so-called branched structure in which the carbon atoms at the ⁇ - and/or ⁇ -position with respect to the mercapto group each combine with three or more atoms other than hydrogens.
- the case where at least one of the substituents is an alkyl group means that at least one of substituents at the ⁇ - and/or ⁇ -position with respect to the mercapto group other than main chain is an alkyl group.
- the main chain indicates the longest structure containing a mercapto group constituted by atoms other than hydrogens.
- mercapto group-containing group a group represented by the following formula (1) is preferred.
- R 1 and R 2 represent each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that at least one of R 1 and R 2 is an alkyl group. That is, both of R 1 and R 2 are not hydrogen atoms simultaneously. In the case where R 1 and R 2 are both alkyl groups, they may be the same or different.
- the alkyl groups having 1 to 10 carbon atoms represented by R 1 and R 2 may be of a straight chain or branched chain. Examples thereof include, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, an n-hexyl group, and an n-octyl group, preferably a methyl group and an ethyl group .
- thiol compound of the present invent in is preferably a polyfunctional thiol compound having two or more mercapto group-containing groups. Specifically, a polyfunctional thiol compound having two or more of the above-mentioned mercapto group-containing groups is more preferred.
- the thiol compound enables photopolymerization with even higher sensitivity as compared with monofunctional compounds.
- the thiol compound of the present invention is preferably one in which the mercapto group-containing group represented by the above-mentioned formula (1) assumes the structure of a carboxylic acid derivative as represented by the formula (3) below.
- Such a thiol compound of the present invention is preferably an ester of a mercapto group-containing carboxylic acid represented by formula (2) below and an alcohol.
- the alcohol is preferably a polyfunctional alcohol.
- Use of the polyfunctional alcohol can give rise to a polyfunctional thiol compound after an esterification reaction.
- polyfunctional alcohol examples include an alkylene glycol (provided that the alkylene group has 2 to 10 carbon atoms and may be branched) , diethylene glycol, glycerol, dipropylene glycol, trimethylolpropane, pentaerythritol, and dipentaerythritol .
- alkylene glycol examples include ethylene glycol trimethylene glycol, 1, 2-propylene glycol, 1, 2-butanediol, 1, 3-butanediol, 2, 3-butanediol, and tetramethylene glycol.
- Preferredpolyfunctional alcohols are alkylene glycols whose main chain has 2 carbon atoms, such as ethylene glycol,
- 2-mercaptoisobutyric acid, 3-mercaptoisobutyric acid, and the like may be exemplified.
- Specific examples of the thiol compound of the present invention having the structure of the formula (1) above include the following compounds.
- hydrocarbon dithiols 2, 5-hexanedithiol, 2,9- decanedithiol, 1, 4-bis (1-mercaptoethyl) benzene, and the like may be exemplified.
- di (1-mercaptoethyl) phthalate, di (2-mercaptopropyl) phthalate, di (3-mercaptobutyl) phthalate, di (3-mercapto- isobutyl) phthalate, and the like may be exemplified.
- Preferred examples thereof include ethylene glycol bis (3-mercaptobutyrate) , propylene glycol bis (3-mercaptobutyrate) , diethylene glycol bis (3-mercaptobutyrate) , butanediol bis (3-mercaptobutyrate) , octanediol bis (3-mercaptobutyrate) , trimethylolpropane tris (3-mercaptobutyrate) , pentaerythritol tetrakis (3-mercaptobutyrate) , dipentaerythritol hexakis (3-mercaptobutyrate) , ethylene glycol bis (2-mercaptopropionate) , propylene glycol bis (2-mercaptopropionate) , diethylene glycol bis (2-mercaptopropionate) , butanediol bis (2-mercaptopropionate) , octanediol bis (2-mercaptopropionate)
- the molecular weight of the thiol compound of the present invention is not particularly limited but is preferably 200 to 1,000.
- the production method for the thiol compound of the present invention is not particularly limited.
- the esters of a mercapto group-containing carboxylic acid and an alcohol can be obtained by reacting the mercapto group- containing carboxylic acid represented by the aforementioned formula (2) and an alcohol by a conventional method to form an ester.
- the conditions of the esterification reaction are not particularly limited and may be selected from a group consisting of the hitherto known reaction conditions appropriately.
- thiol compounds include thiol compounds (A) and (B) described below.
- R 3 to R 6 represent each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
- the alkyl group is preferably a straight chain or branched chain alkyl group having 1 to 3 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group, and more preferably a methyl group and an ethyl group. More preferably, R 3 is a hydrogen atom, a methyl group or an ethyl group, and R 4 to R 6 are hydrogen atoms . Lisa mercapto group-containing group represented by the aforementioned formula (1) .
- the thiol compound (A) is a compound having two mercapto group-containing groups obtained by using a diol whose main chain has 2 carbon atoms as a starting material polyfunctional alcohol. More preferred examples of the thiol compound (A) include those in which the mercapto group is of a secondary group (Al) and those in which the mercapto group is of a tertiary group (A2) .
- L is a mercapto group-containing group represented by the aforementioned formula (1) .
- the thiol compound (B) is a compound having three mercapto group- containing groups obtained by using trimethylolpropane as a starting material polyfunctional alcohol. More preferred examples of the thiol compound (B) include those in which the mercapto group is of a secondary group (B3) and those in which the mercapto group is of a tertiary group (B4) .
- novel thiol compound of the present invention include four kinds of thiol compounds (Al), (A2) , (B3) and (B4) .
- Al thiol compounds
- the diol having 2 carbon atoms in the main chain include ethylene glycol, 1, 2-propylene glycol, and 1, 2-butanediol.
- Preferred specific examples of such a thiol compound (Al) include ethylene glycol bis (3-mercaptobutyrate) , 1, 2-propylene glycol bis (3-mercaptobutyrate) , and 1, 2-butanediol bis (3- mercaptobutyrate) .
- A2 Thiol compound in which the mercapto group is of a tertiary group obtained using a diol having two carbon atoms as a starting material polyfunctional alcohol;
- Preferred specific examples of such a thiol compound (A2) include ethylene glycol bis (2-mercaptoisobutyrate) and 1, 2-propylene glycol bis (2-mercaptoisobutyrate) .
- B3 Thiol compound in which the mercapto group is of a secondary group obtained using a trimethylolpropane as a starting material polyfunctional alcohol;
- Preferred specific examples of such a thiol compound (B3) include trimethylolpropane tris (3-mercaptobutyrate) .
- B4 Thiol compound in which the mercapto group is of a tertiary group obtained using a trimethylolpropane as a starting material polyfunctional alcohol;
- This thiol compound is a thiol compound represented by the formula (B) above, wherein both of R 1 and R 2 in L (the mercapto group-containing group represented by the formula
- thiol compound (B4) include trimethylolpropane tris (2-mercaptoisobutyrate) .
- Photopolymeriza i n initiator composition and photosensitive composition containing the same (1) Photopolymerization initiator composition
- the photopolymerization initiator composition of the present invention contains a thiol compound as described above and a photopolymerization initiator.
- the thiol compound may be used singly or two or more of them may be used in combination.
- photopolymerization initiator general photopolymerization initiators may be used. Preferred examples thereof include ⁇ -hydroxyacetophenones, ⁇ - aminoacetophenones, and biimidazoles .
- Examples of the ⁇ -hydroxyacetophenones include 2-hydroxy-2-methyl-l-phenylpropan-l-one, 2-hydroxy-2-methyl-l-phenylbutan-l-one, 1- (4-methylphenyl) -2-hydroxy-2-methylpropan-l-one, 1- (4-isopropylphehyl) -2-methylpropan-l-one, 1- (4-butylphehyl) -2-hydroxy-2-methylpropan-l-one, 2-hydroxy-2-methyl-l- (4-octylphenyl) propan-1-one, 1- (4-dodecylphehyl) -2-methylpropan-l-one, 1- (4-methoxyphehyl) -2-methylpropan-l-one,
- ⁇ -aminoacetophenones include 2-dimethylamino-2-methyl-l-phenylpropan-l-one, 2-diethylamino-2-methyl-1-phenylpropan-l-one, 2-methyl-2-morpholino-l-phenylpropan-l-one, 2-dimethylamino-2-methyl-l- (4-methylphenyl) propan-1-one, 2-dimethylamino-l- (4-ethylphenyl) -2-methylpropan-l-one, 2-dimethylamino-l- (4-isopropylphenyl) -2-methylpropan-l- one,
- biimidazoles examples include 2, 2 ' -bis (2-chlorophenyl) -4, 4 ' , 5, 5' -tetraphenyl-1, 2 ' - biimidazol,
- benzoin methyl ether benzoin ethyl ether, benzoin isopropyl ether, benzyl methyl ketal, ⁇ - halogenoacetophenones, methyl phenyl glyoxylate, benzyl, anthraquinone, phenanthrenequinone, camphor quinone isophthalophenone, acylphosphine oxide and the like may be used.
- photopolymerization initiators may be used singly or two or more of them may be used in combination.
- the content of the thiol compound is preferably 10 to 90% by mass, and the content of the photopolymerization initiator is preferably 90 to 10% by mass.
- a sensitizer may be used.
- the sensitizer examples include cation dyes such as cyanine, xanthene, oxazine, thiazine, diarylmethane, triarylmethane, and pyrilium, neutral dyes such as merocyanine, coumarin, indigo, aromatic amines, phthalocyanine, azo, quinone, and thioxanthene sensitizing dyes, and compounds such as benzophenones, acetophenones, benzoins, thioxanthones, anthraquinones, imidazoles, biimidazoles, coumarins, ketocoumarins, triphenylpyriliums, triazines, and benzoic acids. Also, acylphosphine oxide, methyl phenyl glyoxylate, ⁇ -acyl oxime ester, benzyl, camphor quinones and the like compounds may be used.
- the counter anions in the case of cation dyes may be any anion, examples of which include halogen ions such as chlorine ion, bromine ion, and iodide ion, benzenesulfonate anion, p-toluenesulphonate anion, methanesulfonate anion, BF 4 anion, PF 6 anion, and perchlorate anion.
- halogen ions such as chlorine ion, bromine ion, and iodide ion
- benzenesulfonate anion p-toluenesulphonate anion
- methanesulfonate anion BF 4 anion
- PF 6 anion and perchlorate anion.
- These compounds may be used singly or two or more of them may be used in combination as the sensitizer. However, theymust be determined in consideration of the light emission pattern of the light source used.
- the cation dyes include cation dyes such as Crystal Violet (C. I. 42555), Methyl Violet (C. I. 42535), Malachite Green (C. I. 42000), Fuchsin (C. I. 42510), Crystal Violet (C. I. 42555), Methyl Violet (C. I. 42535), Malachite Green (C. I. 42000), Fuchsin (C. I. 42510), Crystal Violet (C. I. 42555), Methyl Violet (C. I. 42535), Malachite Green (C. I. 42000), Fuchsin (C. I. 42510), Crystal Violet (C. I. 42555), Methyl Violet (C. I. 42535), Malachite Green (C. I. 42000), Fuchsin (C. I. 42510), Crystal Violet (C. I. 42555), Methyl Violet (C. I. 42535), Malachite Green (C. I. 42000), Fuchsin (C.
- Crystal Violet p-toluenesulfonate, or naphthalene sulfonate Victoria Blue B p-toluenesulfonate or perchlorate, Basic Orange 21 p-toluenesulfonate or BF 4 salt, and Basic Red 5 naphthalenesulfonate or PF 6 salt.
- Electrically neutral dyes include 3-aryl-l-carboxymethyl-5- [2- (3-ethyl-2- (3H) -benzoxazolyl- idene) -2-thiohydantoin, 4- [2- (3-ethyl-2 (3H) -benzothiazolylidene) ethylidene] -3-3- phenyl-2-isooxazolin-5-one,
- 2-methylthioxanthone isopropylthioxanthone, anthraquinone, ethylanthraquinone, chloroanthraquinone, hydroxymethylanthraquinone, aminoanthraquinone, methylaminoanthraquinone, aceanthrenequinone, acenaphthenequinone,
- the compounding amount of the sensitizer in the photopolymerization initiator composition is 5 to 50 mass%.
- the photosensitive composition of the present invention may contain a compound having an ethylenically unsaturated bond and/or a transparent polymer compound, and the above-mentioned photopolymerization initiator composition, and optionally various additives such as a pigment and a solvent.
- photocuring by radical polymerization undergoes polymerization inhibition due to oxygen in the air at the interface with the air so that complete curing becomes difficult. Accordingly, generally photocuring is performed by providing an air-shielding layer such as a cover film lest oxygen should contact the surface or in the presence of an inert gas atmosphere such as argon gas or nitrogen.
- an air-shielding layer such as a cover film
- an inert gas atmosphere such as argon gas or nitrogen.
- the photosensitive composition of the present invention exhibits sufficient curability regardless of whether or not oxygen is present and thus can be used advantageously in application where use of oxygen-shielding membrane is undesirable, for example, as a photosensitive composition for forming color filters.
- the thiol compound of the present invention having a so-called branching structure at the ⁇ -position and/or ⁇ -position in combination with the already-existing photopolymerization initiator in a photosensitive composition, maintenance or improvement of high sensitivity and improvement of storage stability can be achieved mutually compatibly.
- the conventional straight chain type thiols (lauryl mercaptan, octanethiol, HSCH 2 CH 2 C00H derivatives, etc.) and aromatic thiols such as mercaptobenzothiazole, high sensitivity can be achieved but improvement of storage stability cannot be achieved sufficiently.
- the compound having an ethylenically unsaturated bond used in the present invention is a compound generally called monomer or oligomer, which can be cured by a radical polymerization (or crosslinking) reaction.
- specific examples thereof include various (meth) acrylates such as (meth) acrylic acid, methyl (meth) acrylate, butyl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate, ethylene glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, styrene, divinylbenzene, (meth) acrylamide, vinyl acetate, N-hydroxymethyl (meth) acrylamide, dipentaerythritol hexaacrylate, melamine acrylate, and epoxy acrylate prepolymer.
- Use of polyfunctional (meth) acrylic monomers
- ⁇ (meth) acryl means both “methacryl” and “acryl”.
- the polymer compound is capable of forming a uniform film having a thickness of 1 ⁇ m or more.
- it is a transparent polymer compound having a transmittance of 80% or more, more preferably 95% or more over the entire region of wavelength 400 to 700nm in the visible light range.
- the polymer compound which is soluble in developing solutions is preferred.
- the polymer compound include thermosetting resins, thermoplastic resins and photosensitive resins .
- polymers and/or copolymers of polyacrylates, poly- ⁇ -alkyl acrylates, polyamides, polyvinyl acetals, polyurethanes, polycarbonates, polystyrenes, polyvinyl esters, phenol resins, epoxy resins, novolak resins, alkyd resins, etc. may be used singly or two or more of them may be used as mixtures.
- the polymer compound may contain ethylenically unsaturated bonds that can be radically polymerized in order to accelerate curing reaction of the photosensitive composition of the present invention or improve the characteristics of cured product.
- the polymer compound of the present invention is compounded in an amount of generally 1 to 300 parts by mass, preferably 50 to 200 parts by mass, per 100 parts by mass of the compound having an ethylenically unsaturated bond.
- pigments the following may be mentioned. All of them are indicated by color index number. That is, C. I. Pigment Yellow 12, 13, 14, 17, 20, 24, 55, 83, 86, 93, 109, 110, 117, 125, 137, 139, 147, 148, 153, 154, 166, and 168, C.I. Pigment Orange 36, 43, 51, 55, 59, and 61, C.I. Pigment Red 9, 97, 122, 123, 149, 168, 177, 180, 192, 215, 216, 217, 220, 223, 224, 226, 227, 228, and 240, C. I. Pigment Violet 19, 23, 29, 30, 37, 40, and 50, C. I.
- Pigment Blue 15, 15:1, 15:4, 15:6, 22, 60, and 64, C. I. Pigment Green 7, 36, C. I. Pigment Brown 23, 25, and 26, C. I. Pigment Black 7, and Titanium Black, and the like may be exemplified. These pigments may be used singly or two or more of them may be used in combination.
- various additives may be added to the photosensitive composition of the present invention in order to impart viscosity operability, characteristics of cured product, and the like.
- volatile solvents may be added for the purpose of sufficient dispersibility of the components, improvement of operability and adhesion at the time of coating, and adjustment of viscosity.
- volatile solvents include alcohols, ketones and esters.
- they include methanol, ethanol, toluene, cyclohexane, isophorone, cellosolve acetate, diethylene glycol dimethyl ether, ethylene glycol diethyl ether, xylene, ethylbenzene, methyl cellosolve, ethyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, isoamyl acetate, ethyl lactate, methyl ethyl ketone, acetone, cyclohexanone and the like. These may be used singly or two or more of them may be used as mixtures.
- reactive solvents may be used.
- examples thereof include 2-hydroxyethyl (meth) acrylate, methyl (meth) acrylate, n-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, N,N- dimethylaminoethyl (meth) acrylate, N-acryloylmorpholine, N-acryloylpiperidine, N,N-dimethyl (meth) acrylamide, N- vinylpyrrolidone, and N-vinylacetamide. These may be used singly or two or more of themmay be used as mixtures .
- the photosensitive composition of the present invention may further contain fluorescent whiteners, surfactants, plasticizers, flame-retardants, antioxidants, UN absorbents, foaming agents, fungicides, antistatic agents, magnetic materials, electrically conductive materials, antimicrobial/bactericidal agents, porous adsorbents, perfumes, and the like, depending on the purpose.
- the photosensitive composition of the present invention may contain heat polymerization inhibitors in order to prevent polymerization during storage. Specific examples of the heat polymerization inhibitor include p-methoxyphenol, hydroquinone, catechol, tert-butylcatechol, phenothiazine, and methoquinone .
- polymerization inhibitors may be added.
- dispersant may be added as appropriate.
- the dispersant has the effects of helping pigments to be dispersed and of preventing reagllomeration after the dispersion.
- mechanical and physical characteristics of the cured product barium sulfate, calcium carbonate, silica, titania, alumina, aluminum powder and the like extender pigments may be added.
- the compounding ratio of each component in the photosensitive composition of the present invention is not generally prescribed but usually it is as follows.
- the compounding amount of the polymer compound is generally 1 to 300 parts by mass, preferably 50 to 200 parts by mass, per 100 parts by mass of the compound having an ethylenically unsaturated bond.
- the compounding amount of the photopolymerization initiator composition is generally 2 to 400 parts by mass, preferably 20 to 200 parts by mass, per 100 parts by mass of the compound having an ethylenically unsaturated bond.
- the components be compounded such that the thiol compound in the photopolymerization initiator composition is in an amount of generally 1 to 200 parts by weight, preferably 10 to 100 parts by mass, per 100 parts by mass of the compound having an ethylenically unsaturated bond. If the amount of thiol compound is too small, initiation of polymerization may in some cases proceed only inefficiently while if the amount is too large, no further improvement in polymerization initiation function is expected and in addition the thiol compound may give an adverse influence on the physical properties of the cured product, so that both the cases are not preferable.
- the components be compounded such that the sensitizer in the photopolymerization initiator composition is present in an amount of generally 1 to 60 parts by mass, preferably 2 to 30 parts by mass, per 100 parts by mass of the compound having an ethylenically unsaturated bond. If the amount of the sensitizer is too small, it may occur in some cases that no sensitizing effect is obtained while if the amount is too large, it may in some cases occur that the light transmission efficiency is decreased due to light absorption thereby and the polymerization initiation efficiency may be decreased, so that both the cases are not preferable.
- the compounding amount of the pigment is generally 100 to 2,000 parts by mass per 100 parts by mass of the compound having an ethylenically unsaturated bond.
- the photosensitive composition of the present invention can be produced by mixing the above-mentioned components by means of various kinds of dispersing means such as a three-roll mill, a two-roll mill, a sand mill, an attritor, a ball mill, a kneader, and a paint shaker.
- the monomer and photopolymerization initiator may be compounded after the pigment is dispersed.
- the photosensitive composition of the present invention may be coated on substrates, for example those made of glass, aluminum, or a film of polyester such as polyethylene terephthalate (PET) by a coating method such as spray coating, spinner coating, roll coating, screen coating, spread coating, dip coating, or calendar coating.
- a coating method such as spray coating, spinner coating, roll coating, screen coating, spread coating, dip coating, or calendar coating.
- a small amount of silicone- or fluorine-contained surfactant as a leveling agent or defoaming agent may be added to the photosensitive composition of the present invention.
- the coated photosensitive composition is dried by a hot-air oven or a hot plate generally under conditions of 60 to 100°C for 10 to 30 minutes to evaporate the volatile solvent.
- the dried coating film is exposed to light.
- exposure to UV light through a photomask having a pattern may be performed depending on the application.
- the light source generally super-highpressure mercury lamp, metal halide lamp, xenon lamp and the like are used.
- filters having a heat ray cutting property or wavelength selectivity may be used.
- the method of forming a pattern of a certain configuration with the photosensitive composition of the present invention is roughly classified into two types. One is a method of coating the photosensitive composition in a desired configuration and then curing it by irradiation of light. The other is a method of coating the photosensitive composition evenly on a substrate, irradiating light to the photosensitive composition so that the exposed portion forms a desired configuration to cure it, and then removing an unexposed portion by means such as washing, peeling, physical polishing, chemical polishing or the like to form a pattern with the photocured product.
- the pattern formed with the photosensitive composition of the present invention means a photocured product of the photosensitive composition formed on a substrate so as to have a certain configuration.
- the photosensitive composition of the present invention is particularly suitable for development-type resists that form precise patterns.
- inorganic materials such as glass and silicon, metallic materials such as aluminum, stainless steel, and copper, resin materials such as PET, polyester, polyi ide, epoxy resin, polyethylene, and polycarbonate and in addition, paper may be used.
- the surface of the substrates may be subjected to oxidation treatment, acid treatment, plasma treatment, discharge treatment or the like to improve adhesion of the photosensitive composition. Since the photosensitive composition is present on the surface of a substrate, the thickness of the substrate can be set optionally. A resin layer or the like that does not participate in the photoreaction may be provided between the photosensitive composition and the substrate.
- examples of the solvent for the developer include organic solvents such as N-methylpyrrolidone, methanol, ethanol, toluene, cyclohexane, isophorone, cellosolve acetate, diethylene glycol dimethyl ether, ethylene glycol diethyl ether, xylene, ethylbenzene, methyl cellosolve, ethyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, isoamyl acetate, ethyl lactate, methyl ethyl ketone, acetone, cyclohexanone, N,N-dimethylformamide, and acetonitrile as well as aqueous alkali solutions. These may be used singly or two or more of themmay be used in
- aqueous alkali solution aqueous solutions of inorganic salts such as, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate, aqueous solutions of organic salts such as hydroxytetramethylammonium and hydroxytetraethylammonium may be added. These may also be used singly or two or more of them may be used in combination.
- inorganic salts such as, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate
- organic salts such as hydroxytetramethylammonium and hydroxytetraethylammonium
- the reaction mixture was washed with deionized water three times, and then dehydrated and dried over anhydrous magnesium sulfate (manufactured by Junsei Chemicals Co., Ltd.). Then, the toluene was distilled off and the residue was subjected to column chromatography with silica gel to purify EGMB.
- the EGMB obtained by the purification was a colorless transparent liquid and the yield was 7.57 g (45%) .
- the EGMB had a compositional formula of C 10 H 18 O 4 S 2 and a molecular weight of 266.38.
- the PGMB obtained by the purification was a colorless transparent liquid and the yield was 2.80 g (25%) .
- the PGMB had a compositional formula of C 11 H 20 O 4 S 2 and a molecular weight of 280.41.
- the reaction mixture was left to cool and neutralized with 50 ml of an aqueous 5% sodium hydrogen carbonate solution. Further, the reaction mixture was washed with deionized water two times, and then dehydrated and dried over anhydrous magnesium sulfate . Then, the toluene was distilled off and the residue was subjected to column chromatography with silica gel to purify TPMB.
- the TPMB obtained by the purification was a colorless transparent liquid and the yield was 5.63 g (64%) .
- the TPMB had a compositional formula of C 1B H 32 0 6 S 3 and a molecular weight of 440.64.
- the toluene was distilled off and the residue was subjected to column chromatography with silica gel to purify EGMIB.
- the EGMIB obtained by the purification was a white crystal and the yield was 6.08 g (38%) .
- the EGMIB had a compositional formula of C 10 H 18 O 4 S 2 and a molecular weight of 266.38.
- the reaction mixture was neutralized with 200 ml of an aqueous 10% sodium hydrogen carbonate. Further, the reaction mixture was washed with deionized water three times, and then dehydrated and dried over anhydrous magnesium sulfate. Then, the methylene chloride was distilled off and the residue was subjected to column chromatography with silica gel to purify PGMIB.
- the PGMIB obtained by the purification was a colorless transparent liquid and the yield was 4.00 g (24%) .
- the PGMIB had a compositional formula of C 1:L H 20 O 4 S 2 and a molecular weight of 280.41.
- Synthetic Example 6 Synthesis of trimethylolpropane tris (2-mercaptoisobutyrate) (TPMIB)
- TPMIB trimethylolpropane tris (2-mercaptoisobutyrate)
- the reaction mixture was left to cool and neutralized with 50 ml of an aqueous 5% sodium hydrogen carbonate solution. Further, the reaction mixture was washed with deionized water two times, and then dehydrated and dried over anhydrous magnesium sulfate . Then, the toluene was distilled off and the residue was subjected to column chromatographywith silica gel to purify TPMIB.
- the TPMIB obtained by the purification was a white crystal and the yield was 4.50 g (51%) .
- the TPMIB had a compositional formula of C 1B H 32 0 6 S 3 and a molecular weight of 440.64.
- Fig. 1 shows a ⁇ -NMR chart of EGMB. Measurement by X H-NMR was performed in deuterated chloroform by using AMX400 manufactured by Bruker Co.
- 13 C-NMR Fig. 2 shows a 13 C-NMR chart of EGMB. Measurement by 13 C-NMR was performed in deuterated chloroform by using AMX400 manufactured by Bruker Co. and assignment of the peak of each chemical shift was performed. 2 2 ' 1 H 3 4 5 6 4 ' 3 ' H 1 '
- 6-methylene groups 170.7 ppm Carbon atoms of 7-, 7'-, and 7"-carbonyl groups
- Mass spectrometry For the mass spectrometry of TPMB, measurements were performed by using the same apparatus as that for EGMB. The peak corresponding to MH + was detected at the position of m/z
- Melting point was measured by using a melting point measuring apparatus type 510, manufactured by BUCHI Co. The melting point measured was 38°C.
- Mass spectrometry For the mass spectrometry of PGMIB, measurements were performed by using the same apparatus as that for EGMB. The peak corresponding to MH + was detected at the position of m/z
- Melting point was measured by using a melting point measuring apparatus type 510, manufactured by BUCHI Co. The melting point measured was 60°C.
- the photosensitive (colored) composition prepared in this example was called a resist for convenience' s sake .
- resist pattern formation with the alkali developable type resist in which a pigment was dispersed was performed by the following steps.
- First step the step of forming a photosensitive colored resin layer with the photosensitive composition of the present invention on a transparent substrate;
- Second step the step of performing pattern-wise exposure through a pattern mask having a predetermined pattern on the above-mentioned photosensitive colored resin layer;
- Third step the step of performing development treatment of the photosensitive colored resin layer after the above- mentioned pattern exposure to convert the photosensitive resin layer after the curing that remains on the above- mentioned transparent substrate in accordance with the predetermined pattern into a pixel layer;
- Fourth step the step of performing baking of the transparent substrate on which pixel layer is formed (post-baking) .
- the sensitizer having an absorption wavelength region of 250. to 500 nm was used.
- a resin solution 50 parts
- 5.7 part of Lionol Blue E manufactured by Toyo Ink Manufacturing Co. , Ltd.
- 0.3 part of a dispersant BYK-161, manufacturedby BYK Che ie Co .
- a paint conditioner manufactured Asada Iron Works Co., Ltd.
- 50 parts of the blue dispersion, 6.25 parts of trimethylolpropane triacrylate manufactured by Shinnakamura Chemical Industry Co., Ltd. ; trade name NK Ester ATMPT
- 30.75 parts of cyclohexanone were sufficiently mixed in a vessel to prepare a blue resist having about 29% of nonvolatile components (without initiator) .
- each of the resists Examples and Comparative Examples was coated on a 100 mm x 100 mm glass substrate to a dry film thickness of about 10 ⁇ m by using a spin coater and dried in a hot-air oven at 70°C for 20 minutes. This was set in a irradiation spectrophotometer (manufacturedby JASCO Corporation, CT-25CP type) and exposed with automatically varying the exposure time. As a light source, a super-high pressure mercury lamp was used. The substrate after the exposure was developed with an aqueous 0.5% sodium carbonate solution for about 40 seconds and subsequently rinsed with running water and heated at 220°C for 30 minutes to obtain spectrograms.
- Table 2 shows number of remaining development steps with i-line (365 nm) , h-line (405 nm) , and g-line (436 nm) .
- the relationship between the number of steps and exposure amount in the present experimental apparatus is as shown in Table 2. That is, the larger the number of steps, the higher the sensitivity.
- the photosensitive composition of the present invention has high sensitivity and excellent storage stability without forming an oxygen- shielding membrane and hence the present invention can provide a photosensitive composition that can reduce the number of production steps and makes it possible to reduce costs as a result of improvement of productivity.
- photopolymerization initiator composition containing the thiol compound of the present invention can give rise to a photosensitive composition having high sensitivity and excellent storage stability thereby enabling reduction in costs as a result of improvement of productivity.
- the photosensitive composition of the present invention is used advantageously in application fields such as resists for printing plates, color proofs, solder resists, etching resists, color filter resists, holograms, optical imaging, and UN ink.
- it is suitable as a development type resist for forming precise patterns.
Abstract
Description
Claims
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KR1020047013107A KR100976995B1 (en) | 2002-02-28 | 2003-02-27 | Thiol compound, photopolymerization initiator composition and photosensitive composition |
US10/505,778 US7341828B2 (en) | 2002-02-28 | 2003-02-27 | Thiol compound, photopolymerization initiator composition and photosensitive composition |
EP03720880.8A EP1478668B1 (en) | 2002-02-28 | 2003-02-27 | Thiol compound, photopolymerization initiator composition and photosensitive composition |
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- 2003-02-27 AU AU2003224454A patent/AU2003224454A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
WO2003072614A3 (en) | 2004-04-22 |
US7341828B2 (en) | 2008-03-11 |
KR100976995B1 (en) | 2010-08-19 |
CN100523008C (en) | 2009-08-05 |
JP4902608B2 (en) | 2012-03-21 |
KR20040101237A (en) | 2004-12-02 |
EP1478668A2 (en) | 2004-11-24 |
AU2003224454A1 (en) | 2003-09-09 |
US20050153231A1 (en) | 2005-07-14 |
AU2003224454A8 (en) | 2003-09-09 |
CN1656127A (en) | 2005-08-17 |
JP2009035555A (en) | 2009-02-19 |
EP1478668B1 (en) | 2013-04-10 |
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