KR102653345B1 - 전기변색 화합물 및 이를 함유하는 광학 물품 - Google Patents
전기변색 화합물 및 이를 함유하는 광학 물품 Download PDFInfo
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- KR102653345B1 KR102653345B1 KR1020187003637A KR20187003637A KR102653345B1 KR 102653345 B1 KR102653345 B1 KR 102653345B1 KR 1020187003637 A KR1020187003637 A KR 1020187003637A KR 20187003637 A KR20187003637 A KR 20187003637A KR 102653345 B1 KR102653345 B1 KR 102653345B1
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- radical
- branched
- tetrafluoroborate
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 94
- 230000003287 optical effect Effects 0.000 title claims abstract description 17
- -1 pyridinediyl radical Chemical class 0.000 claims description 198
- 239000000203 mixture Substances 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000002441 reversible effect Effects 0.000 claims description 5
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 4
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000002222 fluorine compounds Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 238000006479 redox reaction Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 14
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 213
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
- 239000000243 solution Substances 0.000 description 74
- 239000002904 solvent Substances 0.000 description 70
- 239000002244 precipitate Substances 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000843 powder Substances 0.000 description 56
- 238000003756 stirring Methods 0.000 description 55
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- 238000010992 reflux Methods 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
- 229910020808 NaBF Inorganic materials 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 29
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 238000001914 filtration Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 19
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 19
- 239000007983 Tris buffer Substances 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- NLTIETZTDSJANS-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=NC=C1 NLTIETZTDSJANS-UHFFFAOYSA-N 0.000 description 12
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229960004979 fampridine Drugs 0.000 description 10
- AMKUSFIBHAUBIJ-UHFFFAOYSA-N 1-hexylpyridin-1-ium Chemical group CCCCCC[N+]1=CC=CC=C1 AMKUSFIBHAUBIJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 7
- 125000004957 naphthylene group Chemical group 0.000 description 7
- 150000003222 pyridines Chemical class 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- NQXDAKVRYHXNPE-UHFFFAOYSA-N (2,4-dinitrophenyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O NQXDAKVRYHXNPE-UHFFFAOYSA-N 0.000 description 6
- MCNUBLFKORCVGA-UHFFFAOYSA-N 1-(2,4-dinitrophenyl)pyridin-1-ium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1[N+]1=CC=CC=C1 MCNUBLFKORCVGA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- JBQATDIMBVLPRB-UHFFFAOYSA-N isoliquiritigenin Natural products OC1=CC(O)=CC=C1C1OC2=CC(O)=CC=C2C(=O)C1 JBQATDIMBVLPRB-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PBSCYQUOCOZNHE-QPJJXVBHSA-N (e)-1-(4-methylphenyl)-3-pyridin-4-ylprop-2-en-1-one Chemical compound C1=CC(C)=CC=C1C(=O)\C=C\C1=CC=NC=C1 PBSCYQUOCOZNHE-QPJJXVBHSA-N 0.000 description 4
- VBEAFJMJDDWBDP-UHFFFAOYSA-N 4-(2-pyridin-4-ylphenyl)pyridine Chemical compound C=1C=NC=CC=1C1=CC=CC=C1C1=CC=NC=C1 VBEAFJMJDDWBDP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000033116 oxidation-reduction process Effects 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- 229940032159 propylene carbonate Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OIHZGFWAMWHYPA-UHFFFAOYSA-N xanthylium Chemical class C1=CC=CC2=CC3=CC=CC=C3[O+]=C21 OIHZGFWAMWHYPA-UHFFFAOYSA-N 0.000 description 4
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 3
- MAWKLXRVKVOYLR-UHFFFAOYSA-N 4-(4-pyridin-4-ylphenyl)pyridine Chemical compound C1=NC=CC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=C1 MAWKLXRVKVOYLR-UHFFFAOYSA-N 0.000 description 3
- LJFCQYVWDOGEPV-UHFFFAOYSA-N 4-(6-pyridin-4-ylnaphthalen-2-yl)pyridine Chemical compound C1=NC=CC(C=2C=C3C=CC(=CC3=CC=2)C=2C=CN=CC=2)=C1 LJFCQYVWDOGEPV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical class [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 2
- QCKHVNQHBOGZER-UHFFFAOYSA-N 1,2,4,5-tetrabromobenzene Chemical compound BrC1=CC(Br)=C(Br)C=C1Br QCKHVNQHBOGZER-UHFFFAOYSA-N 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical class BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- FCPNSKVNCMNPIB-UHFFFAOYSA-N 1,3-bis(4-methylphenyl)-5-pyridin-4-ylpentane-1,5-dione Chemical compound N1=CC=C(C=C1)C(CC(CC(=O)C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)=O FCPNSKVNCMNPIB-UHFFFAOYSA-N 0.000 description 2
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 2
- QXBUYALKJGBACG-UHFFFAOYSA-N 10-methylphenothiazine Chemical compound C1=CC=C2N(C)C3=CC=CC=C3SC2=C1 QXBUYALKJGBACG-UHFFFAOYSA-N 0.000 description 2
- SLMHHOVQRSSRCV-UHFFFAOYSA-N 2,3-dibromopyridine Chemical class BrC1=CC=CN=C1Br SLMHHOVQRSSRCV-UHFFFAOYSA-N 0.000 description 2
- JDNKIBDIVWNOTI-UHFFFAOYSA-L 2,5-bis(1-hexylpyridin-1-ium-4-yl)pyridine diiodide Chemical compound [I-].[I-].C(CCCCC)[N+]1=CC=C(C=C1)C1=NC=C(C=C1)C1=CC=[N+](C=C1)CCCCCC JDNKIBDIVWNOTI-UHFFFAOYSA-L 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- ZUZVABZAGDVLSC-UHFFFAOYSA-N 4-(2,3,5,6-tetrafluoro-4-pyridin-4-ylphenyl)pyridine Chemical compound FC=1C(F)=C(C=2C=CN=CC=2)C(F)=C(F)C=1C1=CC=NC=C1 ZUZVABZAGDVLSC-UHFFFAOYSA-N 0.000 description 2
- ZNALFCQVQALKNH-UHFFFAOYSA-N 4-(2,4,5-tripyridin-4-ylphenyl)pyridine Chemical compound C1=NC=CC(C=2C(=CC(=C(C=3C=CN=CC=3)C=2)C=2C=CN=CC=2)C=2C=CN=CC=2)=C1 ZNALFCQVQALKNH-UHFFFAOYSA-N 0.000 description 2
- MBJXDIYHLGBQOT-UHFFFAOYSA-N 4-pyridin-4-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=NC=C1 MBJXDIYHLGBQOT-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- BEIVJADRZCTXEJ-UHFFFAOYSA-N [6-(trifluoromethylsulfonyloxy)naphthalen-2-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=CC2=CC(OS(=O)(=O)C(F)(F)F)=CC=C21 BEIVJADRZCTXEJ-UHFFFAOYSA-N 0.000 description 2
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- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
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- 125000003944 tolyl group Chemical group 0.000 description 2
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
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- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- DTEBZGKINVACPT-FMIVXFBMSA-N (e)-1,3-bis(4-methylphenyl)prop-2-en-1-one Chemical compound C1=CC(C)=CC=C1\C=C\C(=O)C1=CC=C(C)C=C1 DTEBZGKINVACPT-FMIVXFBMSA-N 0.000 description 1
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/1503—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/153—Constructional details
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- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2202/00—Materials and properties
- G02F2202/02—Materials and properties organic material
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- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Eyeglasses (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Plural Heterocyclic Compounds (AREA)
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| EP15306123.9A EP3115433B1 (en) | 2015-07-08 | 2015-07-08 | Electrochromic compounds and optical articles containing them |
| EP15306123.9 | 2015-07-08 | ||
| PCT/EP2016/066052 WO2017005824A1 (en) | 2015-07-08 | 2016-07-06 | Electrochromic compounds and optical articles containing them |
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| KR20180040131A KR20180040131A (ko) | 2018-04-19 |
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| JP6728628B2 (ja) * | 2015-03-13 | 2020-07-22 | 株式会社リコー | エレクトロクロミック化合物、エレクトロクロミック組成物、並びにエレクトロクロミック素子及びエレクトロクロミック調光素子 |
| CN107924098A (zh) | 2015-07-10 | 2018-04-17 | 依视路国际公司 | 具有改善的振幅变化单元的眼科装置 |
| CN106916582A (zh) * | 2015-12-25 | 2017-07-04 | 宁波祢若电子科技有限公司 | 一种阴极电致变色化合物和相关介质与装置 |
| US10310350B2 (en) * | 2016-05-12 | 2019-06-04 | Canon Kabushiki Kaisha | Organic compound, electrochromic compound, and electrochromic element, optical filter, lens unit, imaging device, and window component having same |
| JP6991731B2 (ja) * | 2016-05-12 | 2022-01-12 | キヤノン株式会社 | 有機化合物、エレクトロクロミック化合物、及びそれを有するエレクトロクロミック素子、光学フィルタ、レンズユニット、撮像装置、窓材 |
| EP3345981B1 (en) * | 2017-01-09 | 2020-09-09 | Essilor International | Electrochromic compounds and optical articles containing them |
| JP7030552B2 (ja) * | 2017-02-20 | 2022-03-07 | キヤノン株式会社 | 有機化合物、エレクトロクロミック素子、光学フィルタ、レンズユニット、撮像装置および窓材 |
| EP3367160B1 (en) | 2017-02-22 | 2020-12-16 | Essilor International | Spectacle lens comprising an activable optical filter |
| CN110526861A (zh) * | 2018-05-09 | 2019-12-03 | 中国科学技术大学 | 紫精衍生物、其制备方法与电致变色器件 |
| JP7446719B2 (ja) * | 2018-06-28 | 2024-03-11 | キヤノン株式会社 | 有機化合物およびそれを有するエレクトロクロミック素子、光学フィルタ、レンズユニット、撮像素子及び窓 |
| WO2020004085A1 (ja) * | 2018-06-28 | 2020-01-02 | キヤノン株式会社 | 有機化合物およびそれを有するエレクトロクロミック素子、光学フィルタ、レンズユニット、撮像素子及び窓 |
| EP3923064B1 (en) | 2020-06-12 | 2025-05-21 | Essilor International | Electrochromic solution |
| EP3985046A1 (en) | 2020-10-15 | 2022-04-20 | Essilor International | Crosslinked gel formulation |
| EP4016178A1 (en) | 2020-12-16 | 2022-06-22 | Essilor International | Multilayer structure, electrochromic cell and ophthalmic device incorporating it, and methods for manufacturing the same |
| EP4020066A1 (en) | 2020-12-23 | 2022-06-29 | Essilor International | Optical device forming an electrochromic ophthalmic lens, spectacle glasses incorporating it and method for manufacturing the same |
| EP4194935A1 (en) | 2021-12-10 | 2023-06-14 | Essilor International | Electro-active ophthalmic device satisfying a prescription for power correction(s), manufacturing method and use of a semi-finished hybrid lens |
| CN114524764B (zh) * | 2022-02-18 | 2023-08-18 | 南京邮电大学 | 一类新型不对称紫精化合物及其制备方法与应用 |
| CN117050004A (zh) * | 2022-05-06 | 2023-11-14 | 南京林业大学 | 一类四臂型共轭紫罗精电致变色材料的制备及应用 |
| CN115057867B (zh) * | 2022-06-08 | 2023-09-15 | 吉林大学 | 一种电致变色化合物、器件及其制备方法和应用 |
| CN115651190B (zh) * | 2022-11-07 | 2025-03-28 | 浙江大学衢州研究院 | 一种可显示绿色的三联吡啶类电致变色化合物膜的制备方法和应用 |
| EP4485053A1 (en) | 2023-06-26 | 2025-01-01 | Essilor International | Ophthalmic article |
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| JP2010116483A (ja) * | 2008-11-13 | 2010-05-27 | Ricoh Co Ltd | エレクトロクロミック化合物とこれを担持したエレクトロクロミック組成物およびこれらを有する表示素子 |
| DE102012201673A1 (de) * | 2012-02-06 | 2013-08-08 | Siemens Aktiengesellschaft | Elektrochrome Redoxmaterialien |
| JP2014111710A (ja) * | 2012-11-01 | 2014-06-19 | Ricoh Co Ltd | エレクトロクロミック化合物、エレクトロクロミック組成物及び表示素子 |
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| JPS55139481A (en) * | 1979-04-18 | 1980-10-31 | Hitachi Ltd | Photochromic material |
| US4841021A (en) * | 1987-11-30 | 1989-06-20 | Minnesota Mining And Manufacturing Company | Polypyridinium |
| JPH05170738A (ja) * | 1991-12-25 | 1993-07-09 | Sony Corp | ビオロゲン化合物 |
| EP1763699B1 (fr) | 2004-07-02 | 2011-08-10 | Essilor International (Compagnie Generale D'optique) | Procede de realisation d'un element optique transparent, composant optique intervenant dans ce procede et element optique ainsi obtenu |
| JP4816069B2 (ja) * | 2005-12-26 | 2011-11-16 | ソニー株式会社 | エレクトロクロミック装置 |
| JP5024592B2 (ja) * | 2006-05-09 | 2012-09-12 | ソニー株式会社 | エレクトロクロミック装置 |
| JP2009048141A (ja) * | 2007-08-23 | 2009-03-05 | Sony Corp | エレクトロクロミック化合物、中間体化合物、及び、それらの製造方法、並びに、エレクトロクロミック化合物を用いた光学装置 |
| JP5294301B2 (ja) * | 2008-03-18 | 2013-09-18 | 独立行政法人物質・材料研究機構 | 表示素子 |
| FR2937154B1 (fr) | 2008-10-09 | 2010-11-19 | Essilor Int | Systeme electroactif transparent |
| FR2950710B1 (fr) | 2009-09-28 | 2012-03-16 | Essilor Int | Systemes electrochromes transparents a plusieurs electrodes de polarisation |
| JP5617597B2 (ja) * | 2010-12-17 | 2014-11-05 | 株式会社リコー | エレクトロクロミック化合物、エレクトロクロミック組成物及び表示素子 |
| JP5949012B2 (ja) * | 2012-03-21 | 2016-07-06 | 株式会社リコー | エレクトロクロミック化合物、エレクトロクロミック組成物及び表示素子 |
| JP6213080B2 (ja) * | 2013-09-09 | 2017-10-18 | 株式会社リコー | エレクトロクロミック材料、エレクトロクロミック組成物及びエレクトロクロミック表示素子 |
| EP2848668B1 (en) | 2013-09-17 | 2019-01-09 | Essilor International | Electrochromic two-core viologen derivatives and optical articles containing them |
| JP6399535B2 (ja) * | 2013-12-25 | 2018-10-03 | 株式会社リコー | エレクトロクロミック化合物、エレクトロクロミック組成物、およびこれを用いた表示素子並びに調光素子 |
| JP6728628B2 (ja) * | 2015-03-13 | 2020-07-22 | 株式会社リコー | エレクトロクロミック化合物、エレクトロクロミック組成物、並びにエレクトロクロミック素子及びエレクトロクロミック調光素子 |
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- 2016-07-06 KR KR1020187003637A patent/KR102653345B1/ko active Active
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010116483A (ja) * | 2008-11-13 | 2010-05-27 | Ricoh Co Ltd | エレクトロクロミック化合物とこれを担持したエレクトロクロミック組成物およびこれらを有する表示素子 |
| DE102012201673A1 (de) * | 2012-02-06 | 2013-08-08 | Siemens Aktiengesellschaft | Elektrochrome Redoxmaterialien |
| JP2014111710A (ja) * | 2012-11-01 | 2014-06-19 | Ricoh Co Ltd | エレクトロクロミック化合物、エレクトロクロミック組成物及び表示素子 |
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| WO2017005824A1 (en) | 2017-01-12 |
| US20180194995A1 (en) | 2018-07-12 |
| JP6912462B2 (ja) | 2021-08-04 |
| EP3115433A1 (en) | 2017-01-11 |
| CN107922830B (zh) | 2021-08-20 |
| US10563120B2 (en) | 2020-02-18 |
| JP2018529754A (ja) | 2018-10-11 |
| EP3115433B1 (en) | 2018-10-03 |
| KR20180040131A (ko) | 2018-04-19 |
| CN107922830A (zh) | 2018-04-17 |
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