JP5579624B2 - 光学フィルタ - Google Patents
光学フィルタ Download PDFInfo
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- JP5579624B2 JP5579624B2 JP2010548964A JP2010548964A JP5579624B2 JP 5579624 B2 JP5579624 B2 JP 5579624B2 JP 2010548964 A JP2010548964 A JP 2010548964A JP 2010548964 A JP2010548964 A JP 2010548964A JP 5579624 B2 JP5579624 B2 JP 5579624B2
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- carbon atoms
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- 230000003287 optical effect Effects 0.000 title claims description 109
- 238000006243 chemical reaction Methods 0.000 claims description 138
- GPYLCFQEKPUWLD-UHFFFAOYSA-N 1h-benzo[cd]indol-2-one Chemical class C1=CC(C(=O)N2)=C3C2=CC=CC3=C1 GPYLCFQEKPUWLD-UHFFFAOYSA-N 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 133
- -1 triethylsilyl group Chemical group 0.000 description 94
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- 238000004519 manufacturing process Methods 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 230000001050 lubricating effect Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000010419 fine particle Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000031700 light absorption Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000007754 air knife coating Methods 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000007756 gravure coating Methods 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- 239000002491 polymer binding agent Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- 125000005504 styryl group Chemical group 0.000 description 2
- 150000004763 sulfides Chemical class 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
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- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- YKXIWKSEELONES-UHFFFAOYSA-N 1,3,3,5-tetrabromocyclohexa-1,4-diene Chemical compound BrC1=CC(Br)(Br)C=C(Br)C1 YKXIWKSEELONES-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 description 1
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- AEKZEKVVJXLCSI-UHFFFAOYSA-N 1-naphthalen-1-ylsulfonylnaphthalene Chemical compound C1=CC=C2C(S(=O)(C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 AEKZEKVVJXLCSI-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical group C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- UPZFLZYXYGBAPL-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-dioxolane Chemical compound CCC1(C)OCCO1 UPZFLZYXYGBAPL-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/06—Naphtholactam dyes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/054—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
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Description
R1〜R6及びYは、各々独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、カルボキシル基、水酸基、−NRR’、有機シリル基、置換されていてもよい炭素原子数1〜30のアルキル基、置換されていてもよい炭素原子数6〜30のアリール基、又は置換されていてもよい炭素原子数7〜30のアリールアルキル基を表し、該アルキル基及び該アリールアルキル基中のメチレン基及び該アリール基とナフトラクタム構造との結合は、−O−、−S−、−SO2−、−CO−、−OCO−又は−COO−で中断されていても良く、該メチレン基中の連続したメチレン基は、−CH=CH−又は−C≡C−を表しても良い。
R及びR’は、各々独立して、水素原子、置換されていてもよい炭素原子数1〜30のアルキル基、又は置換されていてもよい炭素原子数6〜30のアリール基を表す。)
上記一般式(I)におけるR1〜R6、Yで表される有機シリル基としては、トリメチルシリル基、トリエチルシリル基、t−ブチルジメチルシリル基、トリイソプロピルシリル基、t−ブチルジフェニルシリル基等が挙げられる。
高い波長変換能を有する色変換フィルタとするためには、R1〜R3及びR5が水素原子であり、R4が上記に好ましいものとして挙げた原子又は基であり、R6が水素原子又はハロゲン原子であることがさらに好ましく、R1〜R6が全て水素原子であるか、又は、R1〜R3及びR5が水素原子であり、R4がハロゲン原子であり、R6が水素原子若しくはハロゲン原子であることが最も好ましい。
また、本発明の光学フィルタを波長変換能を有する色変換フィルタとして用いる上で、上記一般式(I)において、Xは酸素原子であることが好ましい。
波長変換能の観点から好ましいものとして以上に挙げたR1〜R6、X及びYは、耐光性の観点からも好ましいものである。
また、耐光性の観点から特に好ましいYとしては、水素原子又は置換されていてもよい炭素原子数1〜30のアルキル基も挙げられる。
上記ナフトラクタム誘導体は、化学構造によって、波長変換能を有するものと有しないものがある。上記ナフトラクタム誘導体が波長変換能を有するものである場合は、本発明の光学フィルタは、波長変換能を有する色変換フィルタとして用いることができる。波長変換能を有する色変換フィルタである本発明の光学フィルタ(以下、本発明の色変換フィルタともいう)は、例えば、300〜500nmの範囲の光を吸収し、400〜700nmの範囲の光に変換して放出する色変換フィルタとして用いることができる。
上記ナフトラクタム誘導体が波長変換能を有しないものである場合は、本発明の光学フィルタは、例えば300〜700nmの範囲の光を吸収する光吸収フィルタとして用いることができる。
本発明の光学フィルタが波長変換能を有しない場合、本発明の光学フィルタは、例えば上記画像表示装置において色調補正用として用いることができる。
上記一般式(I)で表されるナフトラクタム誘導体を含有する光学機能層120又は光学機能支持体105は、ナフトラクタム誘導体が波長変換能を有しない場合は光吸収層として機能し、ナフトラクタム誘導体が波長変換能を有する場合は色変換層(光吸収層を兼ねる)として機能する。
また、本発明の色変換発光デバイスにおいて、カラーフィルタ層を設けずに、例えば色変換部として図1に示される光学フィルタ(カラーフィルタ層を持たない)を用いる場合、発光部は光学フィルタのいずれかの側に配置されてもよく、また該光学フィルタは光源の表面に直接積層してもよい。
無水1,8−ナフタル酸(0.3mol)、ヒドロキシルアミン塩酸塩(0.3mol)、ピリジン(330.64g)を仕込み、撹拌しながら昇温した。還流下で1時間反応させた後、80℃まで冷却した。そこにp−トルエンスルホン酸クロリド(0.6mol)を粉体で仕込んだ。仕込み終わった後、昇温して還流下で1時間反応した後冷却した。反応液を水1.25L中に加え、30分撹拌して得られた結晶をろ過した。結晶をビーカーに移し、炭酸水素ナトリウム水溶液(1L)、イオン交換水(1L)の順で洗浄し、ろ過、イオン交換水洗浄、乾燥して中間体(収率81.1%)を得た。得られた中間体全量、エタノール(175ml)、水(200ml)を仕込み撹拌した。そこに2.70mol/L水酸化ナトリウム水溶液(325ml)を滴下した。滴下終了後、昇温して還流下でエタノールを留去しながら3時間反応した。反応終了後、75℃まで冷却し、濃塩酸(105ml)を滴下した。滴下途中、60℃で結晶が析出した。滴下終了後、さらに冷却して得られた結晶をろ過し、イオン交換水洗浄、乾燥して目的物38.67g(収率94.0%)を得た。
化合物No.1(0.08mol)、炭酸カリウム(0.40mol)、ジメチルホルムアミド(73.28g)を仕込み、そこにヨウ化メチル(0.096mol)を滴下し、95℃まで昇温した。3時間撹拌後、70℃まで冷却し、イオン交換水(100ml)、酢酸エチル50mlを加え、室温まで戻した。酢酸エチルで抽出後、有機層を水洗、脱溶媒して、目的物11.12g(収率75.7%)を得た。
化合物No.2(0.05mol)のジクロロメタン(131.06g)溶液を−30℃まで冷却し、2,4,4,6−テトラブロモ−2,5−シクロヘキサンジエン(0.055mol)を滴下した。3時間後、室温まで戻しさらに1晩撹拌した。氷浴で冷やしながら、0.85mol/L水酸化ナトリウム水溶液(100ml)を滴下した。これをクロロホルムで抽出後、有機層を水洗、脱溶媒した。得られた抽出物をシリカゲルカラムクロマトグラフィーにて精製し、化合物No.3(9.96g)及び化合物No.4(1.54g)を得た。
化合物No.3(1.00mmol)、ジフェニルアミン(1.05mmol)、ナトリウム−t−ブトキシド(1.40mmol)、トルエン(3ml)を仕込み、アルゴン雰囲気下とした。そこにPd2(dba)3(0.15mmol)、ビフェニル−2−イル−ジ−t−ブチルホスフィン(0.50mmol)を加え、100℃で17時間撹拌した。その後、トルエン抽出し、有機層を水洗、脱溶媒した。得られた抽出物をシリカクロマトグラフィーにて精製し、目的物0.03g(収率8.3%)を得た。
アルゴン雰囲気下、酢酸エチル(2.00mmol)、28%ナトリウムメトキシド/メタノール溶液(2.90g)、化合物No.3(5.00mmol)、ヨウ化銅(0.70mol)を仕込み、8時間還流した。酢酸エチルで抽出後、有機層を水洗、脱溶媒した。得られた抽出物をシリカカラムクロマトグラフィーにて精製し、目的物0.62g(収率58.2%)を得た。
化合物No.3(2.00mmol)、ジフェニルアミン(4.00mmol)、ナトリウム−t−ブトキシド(2.80mmol)、トルエン(6ml)を仕込み、アルゴン雰囲気下とした。そこにPd(OAc)2(0.30mmol)、トリ−t−ブチルホスフィン(0.10mmol)を加え、100℃で8時間撹拌した。その後、トルエン抽出し、有機層を水洗、脱溶媒した。得られた抽出物をシリカクロマトグラフィーにて精製し、目的物0.06g(収率9.7%)を得た。
化合物No.1(5.00mmol)、水酸化カリウム(10.00mmol)、臭化テトラブチルアンモニウム塩(0.20mmol)、テトラヒドロフラン(9.6g)を仕込み、そこに1−ブロモメチル−2,3,4,5,6−ペンタフルオロベンゼン(6.00mmol)を撹拌させながら滴下し、80℃まで昇温した。1時間撹拌後、60℃まで冷却し、イオン交換水(50ml)、酢酸エチル(50ml)を加えた後、室温まで冷却した。酢酸エチルで抽出後、有機相を水洗し、脱溶媒した。得られた抽出物をシリカゲルカラムクロマトグラフィーにて精製し、目的物1.16g(収率66.3%)を得た。
あらかじめ調製した20wt%ポリメチルメタクリレートのトルエン溶液に、λmaxにおける吸光度が0.5となるように、上記[製造例1〜7]で得たナフトラクタム誘導体(化合物No.1〜No.7及び化合物No.172)並びに下記比較化合物No.1〜No.2のいずれかを溶解し、ワイヤーバー(RDS30 R.D.S. Webster,N.Y.)にて100μmポリエチレンテレフタレート(PET)フィルム基板へ塗工後、100℃の条件下10分間オーブンで加熱して本発明の光学フィルタを得た。
得られた光学フィルタについて、吸収スペクトルを日立ハイテクノロジーズ社製分光光度計U−3010を用いて、蛍光スペクトルを日立ハイテクノロジーズ社製分光蛍光光度計F4500を用いて各フィルムのλmaxを励起光として測定した。量子効率は日立ハイテクノロジーズ社製分光蛍光光度計F4500とΦ60積分球ユニットを用いて各フィルムのλmax付近を励起光として測定し、面積比率から算出した。結果を下記[表3]に示す。
実施例1〜8及び比較例1〜2で得られた本発明の光学フィルタに、キセノン耐光性試験機(テーブルサン、スガ試験機(株)社製)にて光を24時間照射し耐光性を評価した。評価においては、光照射前後の各光学フィルタの吸収極大波長λmaxにおける吸光度及び蛍光極大波長FLmaxにおける蛍光強度を測定し、初期値(光照射前)を100として光照射後の相対値(保持率)を算出し、耐光性を比較した。結果を[表4]に示す。
10G 緑色フィルタ層
10B 青色フィルタ層
20R 赤色変換層
20G 緑色変換層
20B 青色変換層
30 ブラックマスク
40 発光層
50 支持体
100 支持体
105 光学機能支持体
110 下塗り層
120 光学機能層
130 反射防止層
140 ハードコート層
150 潤滑層
200 表面シート層
210 透明基板
220 充填剤層
230 集光フィルム
240 光電変換素子
250 バックシート層
Claims (3)
- 下記一般式(I)で表されるナフトラクタム誘導体を少なくとも一種含み、波長変換能を有する色変換フィルタである光学フィルタ。
R1〜R6及びYは、各々独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、カルボキシル基、水酸基、−NRR'、有機シリル基、置換されていてもよい炭素原子数1〜30のアルキル基、置換されていてもよい炭素原子数6〜30のアリール基、又は置換されていてもよい炭素原子数7〜30のアリールアルキル基を表し、
該アルキル基及び該アリールアルキル基中のメチレン基及び該アリール基とナフトラクタム構造との結合は、−O−、−S−、−SO2−、−CO−、−OCO−又は−COO−で中断されていても良く、該メチレン基中の連続したメチレン基は、−CH=CH−又は−C≡C−を表しても良い。
R及びR'は、各々独立して、水素原子、置換されていてもよい炭素原子数1〜30のアルキル基、又は置換されていてもよい炭素原子数6〜30のアリール基を表す。) - 発光部と、請求項1に記載の光学フィルタとを含む色変換発光デバイス。
- 光電変換素子と、請求項1に記載の光学フィルタとを含む光電変換デバイス。
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JP2004335415A (ja) * | 2003-05-12 | 2004-11-25 | Mitsubishi Chemicals Corp | 電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
US20080076188A1 (en) * | 2006-06-19 | 2008-03-27 | Patsenker Leonid D | Luminescent compounds |
JP2009221266A (ja) * | 2008-03-13 | 2009-10-01 | Fujifilm Corp | 顔料微粒子の製造方法 |
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US7332257B2 (en) * | 2003-07-11 | 2008-02-19 | Asahi Glass Company, Limited | Composition for optical film, and optical film |
DE102004006142A1 (de) * | 2004-02-07 | 2005-08-25 | Wella Ag | Neutrale und kationische Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern |
JP2005323590A (ja) | 2004-04-12 | 2005-11-24 | Tokyo Univ Of Science | 鳥獣防止用成形体 |
US7796327B2 (en) * | 2005-03-15 | 2010-09-14 | Fujifilm Corporation | Light transmitting electromagnetic wave shielding film, optical filter and plasma display panel |
JP2006303033A (ja) | 2005-04-18 | 2006-11-02 | National Institute Of Advanced Industrial & Technology | 太陽電池モジュール |
BRPI0617199A2 (pt) * | 2005-10-12 | 2011-07-19 | Ciba Sc Holding Ag | pigmentos luminescentes encapsulados |
JP5321871B2 (ja) | 2005-10-19 | 2013-10-23 | 学校法人東京理科大学 | 農作物栽培用資材及びそれを用いた農作物栽培方法 |
JP4950600B2 (ja) * | 2006-09-05 | 2012-06-13 | 日本電信電話株式会社 | 音響モデル作成装置、その装置を用いた音声認識装置、これらの方法、これらのプログラム、およびこれらの記録媒体 |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5024269A (ja) * | 1972-07-11 | 1975-03-15 | ||
JPS5257167A (en) * | 1975-10-30 | 1977-05-11 | Ciba Geigy Ag | Novel naphtholactamm44 carboxylic acid and derivatives thereof and preparation of the same |
JP2004335415A (ja) * | 2003-05-12 | 2004-11-25 | Mitsubishi Chemicals Corp | 電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
US20080076188A1 (en) * | 2006-06-19 | 2008-03-27 | Patsenker Leonid D | Luminescent compounds |
JP2009221266A (ja) * | 2008-03-13 | 2009-10-01 | Fujifilm Corp | 顔料微粒子の製造方法 |
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US8350054B2 (en) | 2013-01-08 |
US20110152538A1 (en) | 2011-06-23 |
EP2458941A4 (en) | 2013-05-29 |
TWI471310B (zh) | 2015-02-01 |
WO2011010537A1 (ja) | 2011-01-27 |
EP2458941A1 (en) | 2012-05-30 |
TW201116511A (en) | 2011-05-16 |
JPWO2011010537A1 (ja) | 2012-12-27 |
CN102124816A (zh) | 2011-07-13 |
CN102124816B (zh) | 2014-08-06 |
KR20120036786A (ko) | 2012-04-18 |
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