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Epindolidiones-Versatile and Stable Hydrogen-Bonded Pigments for Organic Field-Effect Transistors and Light-Emitting Diodes

机译:用于有机场效应晶体管和发光二极管的依必多立酮通用且稳定的氢键结合颜料。

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摘要

Hydrogen-bonded pigments are remarkably stable high-crystal lattice energy organic solids. Here a lesser-known family of compounds, the epindolidiones, which demonstrates electronic transport with extraordinary stability, even in highly demanding aqueous environments, is reported. Hole mobilities in the range 0.05-1 cm~2 V~(-1) s~(-1) can be achieved, with lower electron mobilities of up to 0.1 cm~2 V~(-1)s~(-1). To help understand charge transport in epindolidiones, X-ray diffraction is used to solve the crystal structure of 2,8-difluoroepin-dolidione and 2,8-dichloroepindolidione. Both derivatives crystallize with a linear-chain H-bonding lattice featuring two-dimensional π-π stacking. Powder diffraction indicates that the unsubstituted epindolidione has very similar crystallinity. All types of epindolidiones measured here display strong low-energy optical emission originating from excimeric states, which coexists with higher-energy fluorescence. This can be exploited in light-emitting diodes, which show the same hybrid singlet and low-energy excimer electroluminescence. Low-voltage FETs are fabricated with epindolidione, which operate reliably under repeated cyclic tests in different ionic solutions within the pH range 3-10 without degradation. Finally, in order to overcome the insolubility of epindolidiones in organic solvents, a chemical procedure is devised to allow solution-processing via the introduction of suitable thermo-labile solubilizing groups. This work shows the versatile potential of epindolidione pigments for electronics applications.
机译:氢键合颜料是非常稳定的高晶格能量有机固体。在这里报道了一个鲜为人知的化合物家族,表皮二酮,即使在高要求的水性环境中也表现出非凡的电子传输稳定性。空穴迁移率可达到0.05-1 cm〜2 V〜(-1)s〜(-1),较低的电子迁移率可达0.1 cm〜2 V〜(-1)s〜(-1) 。为了帮助理解上皮二烯中的电荷传输,使用X射线衍射解决了2,8-二氟庚二酮-二碘和2,8-二氯庚二酮的晶体结构。两种衍生物均以具有二维π-π堆积的线性链H键晶格结晶。粉末衍射表明未取代的表皮二酮具有非常相似的结晶度。此处测量的所有类型的上皮二酮都显示出源自激发态的低能强光发射,并与高能荧光共存。可以在显示相同的混合单线态和低能量准分子电致发光的发光二极管中利用这一点。低压场效应晶体管用表皮二酮制造,在反复循环测试中,在3-10的pH范围内的不同离子溶液中可以可靠地运行而不会降解。最后,为了克服表皮二酮在有机溶剂中的不溶性,设计了一种化学方法以允许通过引入合适的对热不稳定的增溶基团进行溶液处理。这项工作表明了表烯二酮颜料在电子领域的多功能潜力。

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  • 来源
    《Advanced Functional Materials》 |2015年第5期|776-787|共12页
  • 作者单位

    Linz Institute for Organic Solar Cells (LIOS) Johannes Kepler University A-4040, Linz, Austria;

    Dipartimento di Ingegneria Civile Ambientale, del Territorio Edile e di Chimica (DICATECh) Politecnico di Bari, Via Orabona 4 70125, Bari, Italy;

    Linz Institute for Organic Solar Cells (LIOS) Johannes Kepler University A-4040, Linz, Austria,Department of Physics, Faculty of Arts and Sciences Yildiz Technical University, Davutpasa Campus Esenler 34210, Istanbul, Turkey;

    Linz Institute for Organic Solar Cells (LIOS) Johannes Kepler University A-4040, Linz, Austria;

    Institute of Inorganic Chemistry Johannes Kepler University A-4040, Linz, Austria;

    Linz Institute for Organic Solar Cells (LIOS) Johannes Kepler University A-4040, Linz, Austria;

    Institute of Physics, Montanuniversitaet Leoben Franz-Josef-Strasse, 18, 8700, Leoben, Austria;

    Institute of Physics, Montanuniversitaet Leoben Franz-Josef-Strasse, 18, 8700, Leoben, Austria;

    Elettra - Sincrotrone Trieste, S. S. 14 Km 163.5 in Area Science Park 34149, Basovizza, Trieste, Italy;

    Materialwissenschaften und Physik Abteilung fuer Mineralogie, Paris-Lodron Universitaet Salzburg Hellabrunner Str. 34 5020, Salzburg, Austria;

    Solar Energy Institute Ege University Izmir, Turkey;

    Dipartimento di Ingegneria Civile Ambientale, del Territorio Edile e di Chimica (DICATECh) Politecnico di Bari, Via Orabona 4 70125, Bari, Italy;

    Linz Institute for Organic Solar Cells (LIOS) Johannes Kepler University A-4040, Linz, Austria;

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