Solution-processable donor−acceptor molecules consisting of triphenylamine core and 1,8-naphthalimide arms were designed and synthesized by palladium-catalyzed Heck reaction. Dilute solutions of the synthesized compounds show strong absorption peaks in the visible wavelength range from 400 to 550 nm, which can be ascribed to the intramolecular charge transfer. Fluorescence quantum yields of dilute solutions of the synthesized materials range from 0.45 to 0.70, while those of the solid samples are in the range of 0.09−0.18. The synthesized molecules exhibit high thermal stability with the thermal degradation onset temperatures ranging from 431 to 448 °C. The compounds form glasses with glass-transition temperatures of 55−107 °C. DFT calculations show that HOMO and LUMO orbitals are almost entirely localized on the donor and acceptor moieties, respectively. Consequently, the frontier orbital energies for the three synthesized compounds are similar and practically do not depend on the number of 1,8-naphthalimide moieties. Ionization potentials of the solid samples (5.75− 5.80 eV) are comparable. The charge-transporting properties of the synthesized materials were studied using xerographic time-offlight method. Hole mobilities in the layers of the compounds having one and two 1,8-naphthalimide moieties exceed 10 −3 cm 2 •V −1 •s −1 at high electric fields at room temperature. The differences on the hole mobilities between the three synthesized compounds are discussed in the frame of Marcus theory by comparing the reorganization energy and electronic coupling parameters.

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Triplet–triplet annihilation (TTA) is an attractive way to boost the efficiency of conventional fluorescent organic light-emitting diodes (OLEDs). TTA-active anthracene derivatives are often considered as state-of-the-art emitters due to the proper energy level alignment. In this work, TTA properties of a series of highly fluorescent nonsymmetrical anthracene compounds bearing 9-(4-arylphenyl) moiety and 10-(4-hexylphenyl) fragments were assessed. Two different methods to enhance the TTA efficiency are demonstrated. First, the intensity of TTA-based delayed fluorescence directly depended on the intersystem crossing (ISC) rate. This ISC rate can be significantly enhanced in more conjugated compounds due to the resonant alignment of S1 and T2 energy levels. While enhanced ISC rate slightly quenches the intensity of prompt fluorescence, the rise of the triplet population boosts the intensity of resultant delayed fluorescence. Second, the triplet annihilation rate can be significantly enhanced by optimization of triplet exciton diffusion regime in the films of anthracene derivatives. We show that the proper layer preparation technology has a crucial influence on uniformity and energetic disorder of the film. This enhances the nondispersive triplet diffusion and increases the resulting delayed fluorescence intensity.