JP5932787B2 - エレクトロクロミック素子 - Google Patents
エレクトロクロミック素子 Download PDFInfo
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- JP5932787B2 JP5932787B2 JP2013519346A JP2013519346A JP5932787B2 JP 5932787 B2 JP5932787 B2 JP 5932787B2 JP 2013519346 A JP2013519346 A JP 2013519346A JP 2013519346 A JP2013519346 A JP 2013519346A JP 5932787 B2 JP5932787 B2 JP 5932787B2
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- 150000002894 organic compounds Chemical class 0.000 claims description 75
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 34
- 238000010521 absorption reaction Methods 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 17
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 238000003384 imaging method Methods 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003792 electrolyte Substances 0.000 claims description 6
- 230000001747 exhibiting effect Effects 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005011 alkyl ether group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 75
- 230000002093 peripheral effect Effects 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 27
- 238000007254 oxidation reaction Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 230000003647 oxidation Effects 0.000 description 24
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 24
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 230000004044 response Effects 0.000 description 20
- 150000005839 radical cations Chemical class 0.000 description 19
- 238000005259 measurement Methods 0.000 description 16
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
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- 238000010992 reflux Methods 0.000 description 12
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 12
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- 239000012046 mixed solvent Substances 0.000 description 11
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- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical group C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 10
- ZAKDYROLNHVOEL-UHFFFAOYSA-N (2-methoxy-6-propan-2-yloxyphenyl)boronic acid Chemical compound COC1=CC=CC(OC(C)C)=C1B(O)O ZAKDYROLNHVOEL-UHFFFAOYSA-N 0.000 description 9
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 3
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 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
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- 229920006332 epoxy adhesive Polymers 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 229910021397 glassy carbon Inorganic materials 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ZGSVBKAINGAHED-UHFFFAOYSA-N 2,5-dibromo-2-thiophen-2-yl-3h-thiophene Chemical compound S1C(Br)=CCC1(Br)C1=CC=CS1 ZGSVBKAINGAHED-UHFFFAOYSA-N 0.000 description 1
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- UTKPZZGBROTDKR-UHFFFAOYSA-N 2,6-dibromodithieno[2,3-a:2',3'-d]thiophene Chemical compound C1=C(Br)SC2=C1SC1=C2SC(Br)=C1 UTKPZZGBROTDKR-UHFFFAOYSA-N 0.000 description 1
- FHMRWRBNAIDRAP-UHFFFAOYSA-N 5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=C(Br)SC(Br)=C21 FHMRWRBNAIDRAP-UHFFFAOYSA-N 0.000 description 1
- XGQICROVNIZXQH-UHFFFAOYSA-N BC1=C(C)C=C(C)C=C1C Chemical compound BC1=C(C)C=C(C)C=C1C XGQICROVNIZXQH-UHFFFAOYSA-N 0.000 description 1
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 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
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 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
- 238000001556 precipitation Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003077 quantum chemistry computational method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 230000000087 stabilizing effect Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 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
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Description
前記エレクトロクロミック性有機化合物は、エレクトロクロミック特性を示すエレクトロクロミック部位と、前記エレクトロクロミック部位と直接結合している芳香環とから構成され、
前記エレクトロクロミック部位は一つの共役面を形成し、
前記芳香環が有し、かつ前記エレクトロクロミック部位と結合している原子と隣り合う原子は、メチル基以上の体積を有する置換基を有しており、
前記一対の電極の電極間距離が150μm以下であることを特徴とするエレクトロクロミック素子を提供する。
前記エレクトロクロミック性有機化合物は、エレクトロクロミック特性を示すエレクトロクロミック部位と、前記エレクトロクロミック部位と直接結合している芳香環とから構成され、
前記エレクトロクロミック部位は一つの共役面を形成し、
前記芳香環が有し、かつ前記エレクトロクロミック部位と結合している原子と隣り合う原子は、メチル基以上の体積を有する置換基を有しており、
前記一対の電極の電極間距離が150μm以下であることを特徴とするエレクトロクロミック素子である。
* Gaussian 03, Revision D.01,M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria,M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven,K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi,V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega,G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota,R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao,H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross,V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann,O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski,P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg,V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain,O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari,J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford,J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz,I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al−Laham,C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill,
B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople,Gaussian, Inc., Wallingford CT, 2004.
<エレクトロクロミック特性>
合成例に示した化合物をクロロホルムに溶解し、この溶液について紫外可視分光光度計(日本分光株式会社製V−560)を用いて中性状態(消色状態)における吸収スペクトルを測定した。
<EC性有機化合物の酸化還元サイクルの耐久安定性−1>
本発明に係る有機EC性有機化合物A−1、A−7、A−10、および比較例1として公知の化合物Ref−1の酸化還元サイクルに対する耐久安定性を評価した。このRef−1の構造式を下記に示す。
<EC性有機化合物の酸化還元サイクルの耐久安定性−2>
本実施形態に係るEC性有機化合物A−7、A−10、A−12、B−1、B−6、B−10、B−16、B−18および比較例2として公知の化合物Ref−1、Ref−2、Ref−3の酸化還元サイクルに対する耐久安定性を評価した。Ref−2およびRef−3の構造式を下記に示す。
<EC素子の作製>
支持電解質として過塩素酸リチウムを0.1Mの濃度で炭酸プロピレンに溶解させ、次いで本発明に係るEC性有機化合物B−7を20.0mMの濃度で溶解させ、EC媒体を得た。
電極間距離が60μmの素子を用いて、そのエレクトロクロミック特性を評価した。作製直後の本EC素子は可視光領域全域にわたり、80%以上の透過率を示し、高い透明性を有していた。
<単極型素子のEC特性>
EC媒体に含まれるEC性有機化合物を、5.0mMのアノード性EC性有機化合物B−24とし、電極基板としてFTOを用いた以外は実施例4と同様に素子を作製し、電極間距離70μmの単極型素子とした。
<両極型素子のEC特性>
EC媒体に含まれるEC性有機化合物を、30.0mMのアノード性EC性有機化合物B−7と30.0mMのカソード性EC性有機化合物Ref−3とし、支持電解質を過塩素酸テトラブチルアンモニウム(0.1M)とし、電極基板としてFTOを用いた以外は実施例4と同様に素子を作製した。
<EC素子の酸化還元サイクルに対する耐久安定性>
EC媒体に含まれるEC性有機化合物を、6.0mMのアノード性EC性有機化合物A−12とした以外は実施例4と同様に素子を作製し、電極間距離150μmの単極型素子とした。この素子に電圧を2.3V印加すると、化合物A−12の酸化種に由来する吸収(498nm)を示し、着色した。
<EC素子の酸化還元サイクルに対する耐久安定性>
EC媒体に含まれるEC性有機化合物を、6.0mMのアノード性EC性有機化合物B−16を溶解させEC媒体とした以外は実施例4と同様に素子を作製し、電極間距離150μmの単極型素子とした。
<EC素子の酸化還元サイクルに対する耐久安定性>
EC媒体に含まれるEC性有機化合物を、6.0mMのアノード性EC性有機化合物A−12と、6.0mMのカソード性EC性有機化合物Ref−3とした以外は実施例4と同様に素子を作製し、電極間距離150μmの両極型素子とした。
<EC素子の消色応答速度>
実施例9で調製したEC媒体(アノード性EC性有機化合物:6.0mMのA−12/カソード性EC性有機化合物:6.0mMのRef−3)を用いて、3種の電極間距離(60μm、150μm、350μm)の両極型素子を作製し、消色時の応答時間を測定した。
11 透明電極
12 ECを含んだ組成物
13 スペーサー
Claims (14)
- 一対の電極と、前記一対の電極の間に配置されている電解質およびエレクトロクロミック性有機化合物を含んだ組成物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性有機化合物は、エレクトロクロミック特性を示すエレクトロクロミック部位と、前記エレクトロクロミック部位と直接結合しているベンゼン環とから構成され、
前記エレクトロクロミック部位は一つの共役面を形成し、
前記ベンゼン環が有し、かつ前記エレクトロクロミック部位と結合している原子と隣り合う原子は、いずれもメチル基以上の体積を有する置換基を有しており、
前記一対の電極の電極間距離が150μm以下であり、
前記エレクトロクロミック部位は下記構造式から選ばれることを特徴とするエレクトロクロミック素子。
構造式において、前記エレクトロクロミック部位は置換基を有してよく、前記置換基はアルキル基、アリール基、複素環基、アルキルエーテル基、アルコキシ基、アラルキル基から選ばれる。 - 前記エレクトロクロミック部位が有する置換基は、炭素原子数1以上10以下のアルキル基、炭素原子数1以上10以下のアルコキシ基、フェニル基から選ばれることを特徴とする請求項1に記載のエレクトロクロミック素子。
- 前記メチル基以上の体積を有する置換基は、炭素原子数1以上10以下のアルキル基、炭素原子数1以上10以下のアルコキシ基、フェニル基から選ばれることを特徴とする請求項1または2に記載のエレクトロクロミック素子。
- 前記エレクトロクロミック性有機化合物の他に、さらにカソード性エレクトロクロミック性有機化合物を有することを特徴とする請求項1乃至3のいずれか一項に記載のエレクトロクロミック素子。
- 前記エレクトロクロミック性有機化合物はアノード性エレクトロクロミック性有機化合物であることを特徴とする請求項1乃至4のいずれか一項に記載のエレクトロクロミック素子。
- 前記エレクトロクロミック部位の最長吸収波長が、前記ベンゼン環の最長吸収波長より長波長であることを特徴とする請求項1乃至5のいずれか一項に記載のエレクトロクロミック素子。
- 前記エレクトロクロミック部位のHOMOが前記置換基を有するベンゼン環のHOMOより高いことを特徴とする請求項1乃至6のいずれか一項に記載のエレクトロクロミック素子。
- 前記エレクトロクロミック部位がチオフェン環を含むことを特徴とする請求項1乃至7のいずれか一項に記載のエレクトロクロミック素子。
- 前記ベンゼン環が有する置換基は電子供与基であることを特徴とする請求項1乃至8のいずれか一項に記載のエレクトロクロミック素子。
- 前記ベンゼン環の前記電子供与基がアルコキシ基であることを特徴する請求項9に記載のエレクトロクロミック素子。
- 前記エレクトロクロミック性有機化合物はその酸化体が可視域に吸収を有するアノード性エレクトロクロミック性有機化合物であることを特徴とする請求項1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1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たTFTとを有することを特徴とする光学フィルタ。
- 請求項12に記載の光学フィルタと、撮像光学系とを有することを特徴とするレンズユニット。
- 撮像光学系と、請求項13に記載の光学フィルタと、前記光学フィルタを通して撮像する撮像素子とを有することを特徴とする撮像装置。
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