JP2001515120A - 対になったｒｅｄ−ｏｘ系および特定アニオンを有するエレクトロクロミック系 - Google Patents
対になったｒｅｄ−ｏｘ系および特定アニオンを有するエレクトロクロミック系Info
- Publication number
- JP2001515120A JP2001515120A JP2000509781A JP2000509781A JP2001515120A JP 2001515120 A JP2001515120 A JP 2001515120A JP 2000509781 A JP2000509781 A JP 2000509781A JP 2000509781 A JP2000509781 A JP 2000509781A JP 2001515120 A JP2001515120 A JP 2001515120A
- Authority
- JP
- Japan
- Prior art keywords
- independently
- bridge
- alkyl
- hydrogen
- electrochromic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001450 anions Chemical class 0.000 title claims description 51
- 239000000126 substance Substances 0.000 claims abstract description 30
- 238000004132 cross linking Methods 0.000 claims abstract description 6
- 239000012476 oxidizable substance Substances 0.000 claims abstract description 6
- -1 alkane sulfonates Chemical class 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 239000012530 fluid Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 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 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- RIOSJKSGNLGONI-UHFFFAOYSA-N 2-phenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 RIOSJKSGNLGONI-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 230000002441 reversible effect Effects 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
- 239000004033 plastic Substances 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- 238000001228 spectrum Methods 0.000 claims description 7
- 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 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 5
- 229940077388 benzenesulfonate Drugs 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical group C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 5
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 claims description 5
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 4
- ZOZQXFASVITJFG-UHFFFAOYSA-N 3-nitrobenzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1S(O)(=O)=O ZOZQXFASVITJFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000005425 toluyl group Chemical group 0.000 claims description 4
- 238000001075 voltammogram Methods 0.000 claims description 4
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 claims description 3
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000011067 equilibration Methods 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical compound C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 claims description 2
- XNKFCDGEFCOQOM-UHFFFAOYSA-N 1,2-dinitronaphthalene Chemical compound C1=CC=CC2=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C21 XNKFCDGEFCOQOM-UHFFFAOYSA-N 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- IORISFYTXJVNFE-UHFFFAOYSA-N 2,3-dinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O IORISFYTXJVNFE-UHFFFAOYSA-N 0.000 claims description 2
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 claims description 2
- SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- WOWFGZLCKNNPIV-UHFFFAOYSA-N 3-phenylbenzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=2C=CC=CC=2)=C1S(O)(=O)=O WOWFGZLCKNNPIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- WCFUGSZVYJXCNK-UHFFFAOYSA-N amino naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)ON)=CC=CC2=C1 WCFUGSZVYJXCNK-UHFFFAOYSA-N 0.000 claims description 2
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 claims description 2
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229960002903 benzyl benzoate Drugs 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000005487 naphthalate group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- UJJUJHTVDYXQON-UHFFFAOYSA-N nitro benzenesulfonate Chemical compound [O-][N+](=O)OS(=O)(=O)C1=CC=CC=C1 UJJUJHTVDYXQON-UHFFFAOYSA-N 0.000 claims description 2
- GVMDZMPQYYHMSV-UHFFFAOYSA-N octyl benzenesulfonate Chemical compound CCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVMDZMPQYYHMSV-UHFFFAOYSA-N 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 claims 1
- 229930192627 Naphthoquinone Natural products 0.000 claims 1
- UFBYHYOCLXJCEA-UHFFFAOYSA-N benzoyl 2-chlorobenzoate Chemical group ClC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1 UFBYHYOCLXJCEA-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000005357 flat glass Substances 0.000 claims 1
- 150000002791 naphthoquinones Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 238000007789 sealing Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 5
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000004020 conductor Substances 0.000 description 5
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- 239000012038 nucleophile Substances 0.000 description 5
- 238000005204 segregation Methods 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
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- 241001074085 Scophthalmus aquosus Species 0.000 description 3
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- 239000007788 liquid Substances 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
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- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
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- 150000001298 alcohols Chemical class 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
-
- 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
- G02F1/1514—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 characterised by the electrochromic material, e.g. by the electrodeposited material
- G02F1/1516—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 characterised by the electrochromic material, e.g. by the electrodeposited material comprising organic material
-
- 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
- G02F2001/1502—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 complementary cell
-
- 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
- G02F1/1514—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 characterised by the electrochromic material, e.g. by the electrodeposited material
- G02F2001/15145—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 characterised by the electrochromic material, e.g. by the electrodeposited material the electrochromic layer comprises a mixture of anodic and cathodic compounds
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19735733A DE19735733A1 (de) | 1997-08-18 | 1997-08-18 | Elektrochromes System mit gekoppeltem RED-OX-System und speziellen Anionen |
| DE19735733.4 | 1997-08-18 | ||
| PCT/EP1998/004909 WO1999009111A1 (de) | 1997-08-18 | 1998-08-06 | Elektrochromes system mit gekoppeltem red-ox-system und speziellen anionen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001515120A true JP2001515120A (ja) | 2001-09-18 |
| JP2001515120A5 JP2001515120A5 (https=) | 2006-01-05 |
Family
ID=7839290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000509781A Pending JP2001515120A (ja) | 1997-08-18 | 1998-08-06 | 対になったｒｅｄ−ｏｘ系および特定アニオンを有するエレクトロクロミック系 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6417951B1 (https=) |
| EP (1) | EP1015524A1 (https=) |
| JP (1) | JP2001515120A (https=) |
| KR (1) | KR20010022994A (https=) |
| AU (1) | AU733812B2 (https=) |
| CA (1) | CA2300131A1 (https=) |
| DE (1) | DE19735733A1 (https=) |
| WO (1) | WO1999009111A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007503477A (ja) * | 2003-08-21 | 2007-02-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料 |
| JP2019204079A (ja) * | 2018-05-18 | 2019-11-28 | キヤノン株式会社 | エレクトロクロミック素子及びこれを用いた撮像装置、透過率可変窓 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19914304A1 (de) * | 1999-03-29 | 2000-10-05 | Bayer Ag | Elektrochrome Kontrastplatte |
| DE10249054A1 (de) * | 2001-10-26 | 2003-05-08 | Bayer Ag | Elektrochrome Vorrichtung und neue elektrochrome Verbindungen |
| EP2014659A1 (en) * | 2007-06-07 | 2009-01-14 | Universität Osnabrück | New hybrid compounds of nucleobases and organic redox molecules and their use |
| US8593714B2 (en) * | 2008-05-19 | 2013-11-26 | Ajjer, Llc | Composite electrode and electrolytes comprising nanoparticles and resulting devices |
| US20100291706A1 (en) * | 2009-05-15 | 2010-11-18 | Millipore Corporation | Dye conjugates and methods of use |
| DE102009023309A1 (de) * | 2009-05-29 | 2010-12-16 | Siemens Aktiengesellschaft | Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement |
| CN102311729B (zh) * | 2010-06-29 | 2014-04-02 | 比亚迪股份有限公司 | 一种电致变色材料及其制备方法、及防眩目汽车后视镜 |
| US8867116B1 (en) | 2013-03-15 | 2014-10-21 | Gentex Corporation | Distate electrochromic device |
| JP6679564B2 (ja) | 2014-07-18 | 2020-04-15 | ボード オブ トラスティーズ オブ ミシガン ステイト ユニバーシティＢｏａｒｄ Ｏｆ Ｔｒｕｓｔｅｅｓ Ｏｆ Ｍｉｃｈｉｇａｎ Ｓｔａｔｅ Ｕｎｉｖｅｒｓｉｔｙ | レドックスシャトルを含む再充電可能なリチウムイオンセル |
| CN104496888B (zh) * | 2014-12-12 | 2018-03-30 | 宁波祢若电子科技有限公司 | 一种阴极电致变色材料化合物及其电致变色器件 |
| JP7089295B2 (ja) | 2016-11-22 | 2022-06-22 | ボード オブ トラスティーズ オブ ミシガン ステイト ユニバーシティ | 充電式電気化学セルおよび酸化還元フロー電池 |
| AU2018302335B2 (en) * | 2017-07-20 | 2020-07-16 | Board Of Trustees Of Michigan State University | Redox flow battery |
| US12438189B2 (en) | 2018-07-16 | 2025-10-07 | Polyceed Inc. | Polymeric ion-conductive electrolyte sheet |
| US12547040B2 (en) | 2018-07-16 | 2026-02-10 | Polyceed Inc. | Insulated glass unit utilizing electrochromic elements with multipe low-e coatings |
| WO2020018410A1 (en) | 2018-07-16 | 2020-01-23 | Polyceed Inc. | Polymeric compositions for use in variable transmission and electrochemical devices |
| US12509625B2 (en) | 2019-07-30 | 2025-12-30 | Polyceed Inc. | Electrochromic devices using non-halogenated anions |
| WO2021021725A1 (en) | 2019-07-30 | 2021-02-04 | Polyceed Inc. | Electrochromic dyes and their use in electrochromic devices |
| CN116178410B (zh) * | 2023-02-09 | 2024-11-15 | 平湖市浙江工业大学新材料研究院 | 一种硼基电致变色材料及其制备方法和应用 |
| EP4461783A1 (en) * | 2023-05-10 | 2024-11-13 | Essilor International | Electrochromic compounds, compositions and optical articles containing them |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3280701A (en) | 1961-09-05 | 1966-10-25 | Donnelly Mirrors Inc | Optically variable one-way mirror |
| US4902108A (en) | 1986-03-31 | 1990-02-20 | Gentex Corporation | Single-compartment, self-erasing, solution-phase electrochromic devices, solutions for use therein, and uses thereof |
| US5151816A (en) | 1989-12-29 | 1992-09-29 | Donnelly Corporation | Method for reducing current leakage and enhancing uv stability in electrochemichromic solutions and devices |
| JP2523224B2 (ja) * | 1989-12-05 | 1996-08-07 | インターナシヨナル・ビジネス・マシーンズ・コーポレーシヨン | 電荷移動塩及びそれらの使用 |
| US5334333A (en) * | 1990-12-17 | 1994-08-02 | Elf Atochem North America, Inc. | Electroactive compounds, compositions and devices and methods of making the same |
| EP0612826B1 (en) * | 1993-02-26 | 2000-10-04 | Donnelly Corporation | Electrochromic polymeric solid films, manufacturing electrochromic devices using such solid films, and processing for making such solid films and devices |
| WO1996002017A1 (en) * | 1994-07-11 | 1996-01-25 | Moskowskoe Nauchno-Proizvodstvennoe Obiedinenie 'niopik' | Electrochromic compound |
| DE19605451A1 (de) * | 1996-02-15 | 1997-08-21 | Bayer Ag | Elektrochromes System |
| DE19631728A1 (de) * | 1996-08-06 | 1998-02-12 | Bayer Ag | Elektrochrome Anzeigevorrichtung |
| DE19631729A1 (de) * | 1996-08-06 | 1998-02-12 | Bayer Ag | Elektrochromes System |
| DE19735732A1 (de) * | 1997-08-18 | 1999-02-25 | Bayer Ag | UV-geschützte elektrochrome Lösung |
| DE19914304A1 (de) * | 1999-03-29 | 2000-10-05 | Bayer Ag | Elektrochrome Kontrastplatte |
| DE10023765A1 (de) * | 2000-05-15 | 2001-11-22 | Bayer Ag | Elektrochrome Vorrichtung |
-
1997
- 1997-08-18 DE DE19735733A patent/DE19735733A1/de not_active Withdrawn
-
1998
- 1998-08-06 CA CA002300131A patent/CA2300131A1/en not_active Abandoned
- 1998-08-06 KR KR1020007001602A patent/KR20010022994A/ko not_active Withdrawn
- 1998-08-06 EP EP98946284A patent/EP1015524A1/de not_active Withdrawn
- 1998-08-06 JP JP2000509781A patent/JP2001515120A/ja active Pending
- 1998-08-06 WO PCT/EP1998/004909 patent/WO1999009111A1/de not_active Ceased
- 1998-08-06 AU AU93393/98A patent/AU733812B2/en not_active Ceased
- 1998-08-06 US US09/485,758 patent/US6417951B1/en not_active Expired - Fee Related
-
2002
- 2002-05-17 US US10/150,335 patent/US6767481B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007503477A (ja) * | 2003-08-21 | 2007-02-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料 |
| JP4937742B2 (ja) * | 2003-08-21 | 2012-05-23 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料 |
| JP2019204079A (ja) * | 2018-05-18 | 2019-11-28 | キヤノン株式会社 | エレクトロクロミック素子及びこれを用いた撮像装置、透過率可変窓 |
| JP7289692B2 (ja) | 2018-05-18 | 2023-06-12 | キヤノン株式会社 | エレクトロクロミック素子及びこれを用いた撮像装置、透過率可変窓 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010022994A (ko) | 2001-03-26 |
| US6767481B2 (en) | 2004-07-27 |
| DE19735733A1 (de) | 1999-02-25 |
| CA2300131A1 (en) | 1999-02-25 |
| US6417951B1 (en) | 2002-07-09 |
| US20020197486A1 (en) | 2002-12-26 |
| AU733812B2 (en) | 2001-05-24 |
| EP1015524A1 (de) | 2000-07-05 |
| WO1999009111A1 (de) | 1999-02-25 |
| AU9339398A (en) | 1999-03-08 |
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