JP6429575B2 - 新規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 - Google Patents
新規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 Download PDFInfo
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- JP6429575B2 JP6429575B2 JP2014206014A JP2014206014A JP6429575B2 JP 6429575 B2 JP6429575 B2 JP 6429575B2 JP 2014206014 A JP2014206014 A JP 2014206014A JP 2014206014 A JP2014206014 A JP 2014206014A JP 6429575 B2 JP6429575 B2 JP 6429575B2
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- 150000002894 organic compounds Chemical class 0.000 title claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 230000003287 optical effect Effects 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 238000002834 transmittance Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000004040 coloring Methods 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 239000003792 electrolyte Substances 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 230000031700 light absorption Effects 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- -1 WO 3 is known Chemical class 0.000 description 27
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000004185 ester group Chemical group 0.000 description 10
- 238000000034 method Methods 0.000 description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 238000005859 coupling reaction Methods 0.000 description 4
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 4
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
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- 150000005839 radical cations Chemical class 0.000 description 4
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- 125000006850 spacer group Chemical group 0.000 description 4
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
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- 239000007864 aqueous solution Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 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 3
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl 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 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
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- 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 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 2
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- 239000000853 adhesive Substances 0.000 description 2
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- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 239000010949 copper Substances 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical group C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- G02F1/1503—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
[1]
[2]
[4]
[6]
[1]
[2]
[3]
[4]
[5]
[6]
本発明に係る有機化合物は例えば、以下の方法で合成することができる。合成法としては、1)メタ位にハロゲン置換基を有するフェニル基とEC部位であるチオフェン化合物とをカップリング反応させた後、ハロゲン原子とピリジル基を反応させた後ピリジル基をピリジニウム塩に変換する方法、2)ピリジル基が置換されたフェニル基と、EC部位であるチオフェン誘導体とを各々合成した後、両者をカップリング反応で連結した後にピリジル基をピリジニウム塩に変換する方法等が挙げられる。
<例示化合物A−1の合成>
1H−NMR(THF−d8)δ(ppm):9.14(d,2H),8.57(d,2H),8.45(s,1H),8.39(s,1H),8.02−7.97(m,2H),7.73(t,1H),7.66(d,2H),7.55−7.47(m,3H),7.21(s,1H),7.03(s,1H),5.94(s,2H),2.38(s,3H),2.26(s,6H).
<例示化合物B−1の合成>
1H−NMR(THF−d8)δ(ppm):9.09(d,4H),8.57(d,4H),8.19(s,2H),8.04(d,2H),7.83(d,2H),7.76(t,2H),7.64(d,4H),7.54−7.49(m,6H),5.93(s,4H),2.37(s,6H).
<炭酸プロピレンへの溶解度>
実施例1で得られた化合物A−1、実施例2で得られた化合物B−1、および比較例として化合物A−1のピリジニウム塩前駆体Ref−1の3つの化合物について、EC素子溶媒である炭酸プロピレンへの溶解度を測定した。
電解質として過塩素酸テトラブチルアンモニウムを0.1Mの濃度で炭酸プロピレンに溶解させ、次いで実施例1の有機化合物A−1を40.0mMの濃度で溶解させ、EC媒体を得た。
11 透明電極
12 EC化合物を含んだ組成物
13 スペーサー
Claims (15)
- 下記一般式[1]で示されることを特徴とする有機化合物。
[1]
式中、A1乃至A6は水素原子、炭素原子数1以上20以下のアルキル基、炭素原子数1以上20以下のアルコキシ基、アリール基からそれぞれ独立に選ばれる置換基を表す。
前記アリール基は置換基を有してもよい。前記アリール基が置換基を有する場合、前記置換基はハロゲン原子、炭素原子数1以上4以下のアルキル基、炭素原子数1以上4以下のアルコキシ基、アリール基、アラルキル基、置換アミノ基、置換シリル基から選ばれる。
nは1以上4以下の整数である。
式中、Bは水素原子または一般式[2]で表わされる置換基である。複数のBは同じであっても異なっていてもよい。ただし、前記複数のBのうち少なくとも1つは一般式[2]で表わされる置換基である。
一般式[2]中のX−は陰イオンを表す。
R2は炭素原子数1以上20以下の置換基を有していてもよいアルキル基または置換基を有していてもよいアリール基を表わす。
[2]
一般式[1]におけるYは、一般式[4]または[6]の構造である。nが2以上の場合、複数のYは下記一般式[4]または[6]よりそれぞれ独立に選ばれる。
[4]
[6]
式中、R 4 及びR 5 、R 8 及びR9は水素原子、ハロゲン原子、炭素原子数1以上20以下のアルキル基、炭素原子数1以上20以下のアルコキシ基、置換基を有していてもよいアリール基、炭素原子数1以上20以下アルキルエステル基、置換基を有していてもよいアミノ基、またはシアノ基からそれぞれ独立に選ばれる。 - 一般式[1]における前記Yは、一般式[6]で表される構造であることを特徴とする請求項1に記載の有機化合物。
- 前記X−が、PF6 −、ClO4 −、BF4 −、AsF6 −、SbF6 −、CF3SO3 −、(CF3SO2)2N−、Br−、Cl−、I−のいずれかである請求項1または2に記載の有機化合物。
- 前記X−が、PF6 −、ClO4 −、BF4 −、(CF3SO2)2N−のいずれかである請求項1乃至3のいずれか一項に記載の有機化合物。
- 前記R2が、ベンジル基である請求項1乃至4のいずれか一項に記載の有機化合物。
- 前記A1乃至前記A4の少なくとも一つが前記アルキル基、前記アルコキシ基または前記置換基を有してもよいアリール基のいずれかである請求項1乃至5のいずれか一項に記載の有機化合物。
- 一対の電極と、前記一対の電極の間に配置されているエレクトロクロミック層を有するエレクトロクロミック素子であって、
前記エレクトロクロミック層は、エレクトロクロミック化合物および電解質を有し、前記エレクトロクロミック化合物は請求項1乃至6のいずれか一項に記載の有機化合物であることを特徴とするエレクトロクロミック素子。 - 前記エレクトロクロミック層は前記有機化合物とは、別種の第2のエレクトロクロミック化合物をさらに有する請求項7に記載のエレクトロクロミック素子。
- 前記第2のエレクトロクロミック化合物は、還元状態における可視光の透過率が酸化状態における可視光の透過率よりも低い化合物である請求項8に記載のエレクトロクロミック素子。
- 着色時における可視光の吸収率の最大値と、着色時における可視光の吸収率の最小値との差が34%以下である請求項7乃至9のいずれか一項に記載のエレクトロクロミック素子。
- 着色時における可視光の吸収率の最大値と、着色時における可視光の吸収率の最小値との差が10%以下である請求項7乃至10のいずれか一項に記載のエレクトロクロミック素子。
- 請求項7乃至11のいずれか一項に記載のエレクトロクロミック素子と、前記エレクトロクロミック素子に接続されている能動素子とを有することを特徴とする光学フィルタ。
- 複数のレンズと、請求項12に記載の光学フィルタとを有することを特徴とするレンズユニット。
- 請求項12に記載の光学フィルタと、前記光学フィルタを通過した光を受光する受光素子とを有することを特徴とする撮像装置。
- 一対の透明基板と、前記一対の基板の間に配置されている請求項7乃至11のいずれか一項に記載のエレクトロクロミック素子と、前記エレクトロクロミック素子に接続されている能動素子とを有することを特徴とする窓材。
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US14/557,283 US9310660B2 (en) | 2013-12-03 | 2014-12-01 | Organic compound and electrochromic element including the same |
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US10344208B2 (en) | 2014-06-09 | 2019-07-09 | iGlass Technology, Inc. | Electrochromic device and method for manufacturing electrochromic device |
US10294415B2 (en) | 2014-06-09 | 2019-05-21 | iGlass Technology, Inc. | Electrochromic composition and electrochromic device using same |
JP6672611B2 (ja) * | 2014-07-03 | 2020-03-25 | 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及び調光素子 |
JP6991738B2 (ja) | 2016-07-23 | 2022-01-13 | キヤノン株式会社 | エレクトロクロミック装置、光学フィルタ、レンズユニット、撮像装置、窓材、及び駆動方法 |
WO2019143401A2 (en) * | 2017-11-20 | 2019-07-25 | Georgia Tech Research Corporation | Anodically coloring electrochromic molecules, materials, and devices, and methods of making and use thereof |
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