Synthesis of New Vat Dyes for Organic Electronics Applications

具有pi-共轭结构的还原染料作为制备各种有机电子应用的高效半导体材料的潜在构件正引起人们的极大关注。这些染料的最大优点之一是它们在可见光范围内的光学性能，使它们对有机太阳能电池(OSC)和染料敏化太阳能电池(DSC)以及有机发光二极管(OLED)应用都很有吸引力。此外，它们巨大的富含碳的刚性圆周率共轭结构使其具有优异的电荷传输特性，可用于有机场效应晶体管(OFET)和电池应用。其他值得注意的优点是，由于制备它们所需的几个廉价的合成步骤，它们在批量购买时成本非常低，它们具有高的环境、热稳定性和化学稳定性，并且可以进行化学转化来改变它们的性质。最近，许多研究人员对还原染料的化学进行了探索，最终将其作为有机电子应用中的活性成分。事实上，大多数还原染料都具有一个大的圆周率共轭体系，在可见光谱的低能区提供有效的光吸收，使它们成为制备有机半导体捕光材料的非常有趣的构件。此外，基于还原染料的小分子和聚合物非常有效地堆积在薄膜状态下，最大p重叠，这对电荷传输特性非常有利。这对场效应管的发展尤为重要，因为场效应管的效率强烈地依赖于薄膜的形貌。最后，基于还原染料的分子可以通过简单的衍生化得到高发射性，这使得它们成为有机发光二极管(OLED)应用的有趣候选者。在这个项目中，我们建议用还原橙1，一种非常常见的低成本还原染料制备有机半导体，并在有机电子器件中进行测试。虽然合成和基本物理表征将在Morin教授的实验室完成，但所有电子设备的测试，主要是场效应晶体管(OFET)，将在德国的Weitz教授实验室进行。

Vat dyes possessing a pi-conjugated structure are drawing considerable attention as potential building blocks for the preparation of highly efficient semiconducting materials for various organic electronic applications. One of the biggest advantages of these dyes is their optical properties in the visible range, making them attractive for both organic solar cells (OSCs) and dye-sensitized solar cells (DSSCs), and for organic light-emitting diode (OLED) applications. In addition, their large carbon-rich, rigid pi-conjugated structure allows for excellent charge transport properties that could be exploited in organic field-effect transistors (OFETs) and battery applications. Other noteworthy advantages are their very low cost when bought in bulk owing to the few, inexpensive synthetic steps required to prepare them, their high environmental, thermal and chemical stability, and the possibility of performing chemical trans- formation to change their properties. Recently, many researchers have explored the chemistry of vat dyes to eventually introduce them as the active component in organic electronic applications. In fact, most of the vat dyes possess a large pi-conjugated system that provides efficient light absorption in the low energy region of the visible spectrum, making them very interesting building blocks for the preparation of light-harvesting semiconductors for OSCs. Moreover, small molecules and polymers based on vat dyes packed very efficiently with a maximum p overlap in the thin-film state, which is highly beneficial to charge transport properties. This is particularly critical for the development of OFETs, whose efficiency strongly depends on the thin-film morphology. Finally, vat dye-based molecules can be made highly emissive by simple derivatization, which makes them interesting candidates for organic light-emitting diode (OLED) applications. In this project, we propose to prepare organic semiconductors made from vat orange 1, a very common and low-cost vat dye, and tests them in organic electronics devices. While the synthesis and basic physical characterization will be achieved in Prof. Morin's lab, all the testing in electronic devices, mostly field-effect transistors (OFETs), will be performed in Prof. Weitz lab in Germany.