JP5836815B2 - 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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- JP5836815B2 JP5836815B2 JP2012011300A JP2012011300A JP5836815B2 JP 5836815 B2 JP5836815 B2 JP 5836815B2 JP 2012011300 A JP2012011300 A JP 2012011300A JP 2012011300 A JP2012011300 A JP 2012011300A JP 5836815 B2 JP5836815 B2 JP 5836815B2
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- 150000002894 organic compounds Chemical class 0.000 title claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 230000003287 optical effect Effects 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 8
- 239000003792 electrolyte Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 56
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical group C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 35
- 230000003647 oxidation Effects 0.000 description 33
- 238000007254 oxidation reaction Methods 0.000 description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 31
- 238000010521 absorption reaction Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 230000035699 permeability 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
- 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
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000002468 redox effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 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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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Description
R4で表される置換基も一般式[2]と同様である。
<例示化合物B−2の合成>
1H−NMR(CDCl3)σ(ppm):7.42(d,4H),7.25−7.21(m,6H),7.18(t,2H),6.51(d,2H),6.50(d,2H),4.40(m,2H),3.61(s,6H),1.20−0.90(s(br),12H).
13C−NMR(CDCl3)σ(ppm):159.39,157.23,139.96,136.25,133.90,130.71,130.59,129.90,128.19,127,73,126.94,113.08,106.41,103.48,70.10,55.74,21.65.
<例示化合物B−1の合成>
1H−NMR(CDCl3)σ(ppm):7.41(d,4H),7.29−7.22(m,6H),7.19(t,2H),6.53(d,4H),3.59(s,12H).
13C−NMR(CDCl3)σ(ppm):159.03,140.28,136.09,134.11,130.75,130.19,130.08,128.15,127.66,127.01,112.13,104.12,55,79.
<酸化還元サイクルの安定性>
実施例1で得られた化合物B−2、実施例2で得られた化合物B−1、および比較例として本発明の置換基より立体障害が小さいtert−ブチル基を置換基としてDTT(ジチエノ[3,2−b:2’,3’−d]チオフェン)に導入した化合物(XX−4)について、酸化還元サイクル耐久性の測定を行った。
<酸化吸収スペクトルの測定(π−ダイマー形成の有無)>
実施例1で得られた化合物B−2、および実施例2で得られた化合物B−1について、酸化時の吸収スペクトルを測定し、π−ダイマー形成の有無の確認を行った。
<例示化合物D−11の合成>
1H−NMR(CDCl3)δ(ppm):7.94(d,4H),7.49(d,4H),7.25(t,2H),6.51(d,2H),6.50(d,2H),4.41(m,2H),3.88(s,6H),3.60(s,6H),1.20−0.90(s(br),12H).
13C−NMR(CDCl3)δ(ppm):167.01,159.17,157.09,140.92,139.47,132.86,132.40,130.99,130.31,129.66,128.44,127.60,112.39,106.29,103.45,70.15,55.70,52.04,21.65.
得られた化合物D−11の酸化吸収スペクトルの測定を、実施例4と同様にテトラブチルアンモニウム過塩素酸塩のジクロロメタン溶液(0.1mol/L)中、D−11を溶解(5.0×10−4mol/L)した溶液で行った。D−11の溶液は、酸化に伴い赤紫色に着色し541.5nmに光吸収ピークを示すとともに、透過率は36.3%まで低下した。この酸化着色状態は、還元により再度無色透明に戻り、酸化還元に伴うエレクトロクロミック特性が確認された。また、この酸化吸収ピークの形状や吸収波長は濃度により変化を示さなかったことから、実施例4と同様にπ−ダイマー形成が抑制されていることが示された。
2 フェニル基
Claims (8)
- 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]
一般式[1]において、A1乃至A4はそれぞれ独立に水素原子、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、アリール基から選ばれる。ただし、A1乃至A4の少なくともひとつは前記アルキル基または前記アルコキシ基または前記アリール基である。
前記アリール基は炭素原子数1以上4以下のアルキル基または炭素原子数1以上4以下のアルコキシ基を置換基として有してよい。
R1乃至R4はそれぞれ独立に水素原子、ハロゲン原子、または、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、炭素原子数1以上20以下のアルキルエステル基、アリール基、シアノ基を表す。
前記アリール基は炭素数1以上4以下のアルキル基を置換基として有してよい。 - 前記A1乃至A4の少なくともひとつは炭素原子数1以上20以下のアルコキシ基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A1乃至A4の少なくともひとつはメトキシ基またはイソプロポキシ基であることを特徴とする請求項2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および電解質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、請求項1乃至3のいずれか一項に記載の有機化合物を有す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および前記電解質層が溶液層であることを特徴とする請求項4に記載のエレクトロクロミック素子。
- 請求項4または5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スイッチング素子と、を有することを特徴とする光学フィルタ。
- 請求項6に記載の光学フィルタと、レンズとを有することを特徴とするレンズユニット。
- 請求項6に記載の光学フィルタと、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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