The development of high-performance n-type organic semiconductors with herringbone molecular assembly

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In this fiscal year, my research focused on the molecular designs for effective solid-state packing structures with strong and balanced intermolecular orbital overlaps and resilience towards dynamic disorders in high-performance n-type organic semiconductors. The electron-deficient benzo[de]isoquinolino[1,8-gh]quinolinetetracarboxylic diimide (BQQDI) π-electron system is continuously used as the molecular design template and various substituents are incorporated to fine-tune the molecular assembly. With the use of bulky substituents on the BQQDI π-electron system, we achieved a two-dimensional isotropic packing motif and an isotropic charge transport for electron carriers. We demonstrated for the first time that the isotropic electron-carrier transport provides resilience to dynamic disorders and it is extremely beneficial for achieving high electron-carrier mobilities. We experimentally confirmed the isotropic charge transport and obtained an excellent air-stable electron mobility up to 3.0 cm2/Vs using four-probe field-effect transistors. In addition to this study, we also developed a synthetically and functionally versatile electron-deficient benzo[de]isoquinolino[1,8-gh]quinoline Diamide π-electron system that can access a wide range of orbital energies for various organic electronic applications including organic field-effect transistors and organic photovoltaics.