9H-Quinolino[3,2,1-k]phenothiazine: A New Electron-Rich Fragment for Organic Electronics

Abstract : A new electron-rich fragment, namely the qui-nolinophenothiazine (QPTZ) is reported. TheQ PTZ fragment incorporated in spiroconfigured materials leads to higher performance in blue Phosphorescent OLEDs than structurally related phenylacridine and indoloacridine based materials (increasing the HOMO energy level,m od-ulating the spin-orbit coupling, etc.) and leads to highly efficient blue phosphorescent organic light emitting diodes, indicatingt he strongp otential of this new molecular fragment in organic electronics. Over the last 30 years,t he fantastic emergence of organic electronics is assignable to the design,t he synthesis and the study of thousands of organic semiconductors (OSCs) with specific properties fitting with the different electronic devices. [1–4] Since the discoveryo ft he " host/guest concept " in phosphorescent organic light-emitting diodes (PhOLEDs), [5] the designo fO SCs usable as host materials for blue-emitting phosphors has been an intense research field worldwide. [4] In addition to its high thermal/morphological stabilitya nd its high triplet energy (E T), an ideal host should also possess ab ipolar character,w ith HOMO and LUMO energy levels adapted to the Fermi levels of the electrodes. [6–9] However,t here is ac ertaina ntinomy between ah igh E T (essential to insure efficient energy transfers) and as hort HOMO/LUMO gap (essential to insure efficient charge injection) and the best trade-off should be found for the ideal host. If the nature of the linkage [10] between the electron rich and the electron-poor units is of key importance to control the E T as well as the HOMO/LUMO gap, their intrinsic properties remainn everthelesst he most important characteristics. In this context, the widely known electron-rich carbazole fragment has led to impressive breakthroughs and is nowadays an important buildingb lock in organic electronics. [11, 12] Around the molecular structure of carbazole, many other car-bazole-like fragments have been developed in the recent years sometimes surpassing the performance of the carbazole fragment in electronics. Thus, indolocarbazole (IC), [13] phenylacri-dine (PA) [14–16] and more recentlyi ndoloacridine (IA) [17] are nowadays key building blocks, widely used in all organic electronic devices (Scheme 1). As the future of organic electronics strongly relies on the discoveryo fn ovel elementarym olecular fragments, such as the new bithiophenesulfonamide building block recently reported by Marks,F acchettie ta l., [19] we wish to report herein an ew promising electron-rich core, namely the quinolinophe-Scheme1.Phenylacridine (PA, left), [14, 18] indoloacridine(IA, middle) [17] and quinolinophenothiazine (QPTZ,r ight) based semiconductors.
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Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22, pp.17930 - 17935. 〈10.1002/chem.201603659〉
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Cyril Poriel, Joëlle Rault-Berthelot, Sébastien Thiery, Cassandre Quinton, Olivier Jeannin, et al.. 9H-Quinolino[3,2,1-k]phenothiazine: A New Electron-Rich Fragment for Organic Electronics. Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22, pp.17930 - 17935. 〈10.1002/chem.201603659〉. 〈cea-01414714〉

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