Phenoxy-benzothiadiazole dyes: Synthesis,photophysical properties and preliminary application in OLEDs |
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Authors: | Alessandra Pazini Luis Maqueira Harold C. Avila Felipe M. Valente Rian E. Aderne Davi Back Ricardo Q. Aucélio Marco Cremona Jones Limberger |
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Affiliation: | 1. Department of Chemistry, Pontifical Catholic University of Rio de Janeiro, Rua Marquês de São Vicente, 225, Gávea, 22451-900 Rio de Janeiro, RJ, Brazil;2. Department of Physics, Pontifical Catholic University of Rio de Janeiro, Rua Marquês de São Vicente, 225, Gávea, 22451-900 Rio de Janeiro, RJ, Brazil;3. Laboratory of Inorganic Materials, Department of Chemistry – UFSM, Av. Roraima 1000, 97105-900 Santa Maria, RS, Brazil |
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Abstract: | The synthesis of a phenoxy-benzothiadiazole (BTD) derivative is reported for the first time. This derivative was employed as an intermediate in the obtention of two novel highly fluorescent aryl-phenoxy-BTD dyes. Their photophysical properties were evaluated in solution and the results indicate a strong intramolecular charge transfer (ICT) character in the excited state. The luminophore 3a, possessing a donor-BTD-phenoxide architecture, exhibits superior fluorescence quantum yield (0.67) than the designed acceptor-BTD-phenoxide dye (0.06). After electrochemical and photoluminescence characterization of thin films of 3a, an OLED with the configuration ITO/PEDOT:PSS/3a/TPBi/LiF/Al was constructed. This device displayed a green emission centered at 547?nm, with CIE coordinates of (0.40, 0.55). For comparison, an OLED using a previously reported luminescent BTD-pyridyl derivative was also constructed. The OLED made with the phenoxy-BTD derivative operated using less current density and led to higher irradiance and electrical stability, indicating the high potential of ArO-BTD dyes for future application in electroluminescent devices. |
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Keywords: | Benzothiadiazole Fluorescence OLED Cross-coupling Phenoxy |
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