A series of bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline end-capped oligoarylenes, BCPA-Ars, are synthesized by double palladium-catalyzed cross-coupling reactions. By using this bis(carbazol-9-yl)triphenylamine moiety as an end-cap, we are able to reduce the crystallization and retain the high-emission ability of these planar fluorescent oligoarylene cores in the solid state, as well as improve the amorphous stability and solubility of the materials. The results of optical and electrochemical studies show that their HOMOs, LUMOs, and energy gaps can be easily modified or fine-tuned by either varying the degree of π-conjugation or using electron affinities of the aryl cores which include fluorene, oligothiophenes, 2,1,3-benzothiadiazole, 4,7-diphenyl-4-yl-2,1,3-benzothiadiazole, and 4,7-dithien-2-yl-2,1,3-benzothiadiazole. As a result, their emission spectra measured in solution and thin films can cover the full UV-vis spectrum (426-644 nm). Remarkably, solution-processed nondoped BCPA-Ars-based OLEDs could show moderate to excellent device performance with emission colors spanning the whole visible spectrum (deep blue to red). Particularly, the RGB (red, green, blue) OLEDs exhibit good color purity close to the pure RGB colors. This report offers a practical approach for both decorating the highly efficient but planar fluorophores and tuning their emission colors to be suitable for applications in nondoped and solution-processable full-color emission OLEDs.
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http://dx.doi.org/10.1021/jo4008332 | DOI Listing |
J Org Chem
July 2013
Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, 34190 Thailand.
A series of bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline end-capped oligoarylenes, BCPA-Ars, are synthesized by double palladium-catalyzed cross-coupling reactions. By using this bis(carbazol-9-yl)triphenylamine moiety as an end-cap, we are able to reduce the crystallization and retain the high-emission ability of these planar fluorescent oligoarylene cores in the solid state, as well as improve the amorphous stability and solubility of the materials. The results of optical and electrochemical studies show that their HOMOs, LUMOs, and energy gaps can be easily modified or fine-tuned by either varying the degree of π-conjugation or using electron affinities of the aryl cores which include fluorene, oligothiophenes, 2,1,3-benzothiadiazole, 4,7-diphenyl-4-yl-2,1,3-benzothiadiazole, and 4,7-dithien-2-yl-2,1,3-benzothiadiazole.
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