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Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs

Three novel small organic heterocyclic compounds: 2-(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound A), 1,3-di(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound B), and 1,3,6,8-tetra(1,2-diphenyl)-1H-benzimidazolepyrene (compound C) were synthesized and characterized for possi...

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Autores principales: De Silva, Thenahandi Prasanthi Deepthika, Youm, Sang Gil, Fronczek, Frank R., Sahasrabudhe, Girija, Nesterov, Evgueni E., Warner, Isiah M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588490/
https://www.ncbi.nlm.nih.gov/pubmed/34770936
http://dx.doi.org/10.3390/molecules26216523
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author De Silva, Thenahandi Prasanthi Deepthika
Youm, Sang Gil
Fronczek, Frank R.
Sahasrabudhe, Girija
Nesterov, Evgueni E.
Warner, Isiah M.
author_facet De Silva, Thenahandi Prasanthi Deepthika
Youm, Sang Gil
Fronczek, Frank R.
Sahasrabudhe, Girija
Nesterov, Evgueni E.
Warner, Isiah M.
author_sort De Silva, Thenahandi Prasanthi Deepthika
collection PubMed
description Three novel small organic heterocyclic compounds: 2-(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound A), 1,3-di(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound B), and 1,3,6,8-tetra(1,2-diphenyl)-1H-benzimidazolepyrene (compound C) were synthesized and characterized for possible applications as blue OLED emitters. The specific molecular design targeted decreasing intermolecular aggregation and disrupting crystallinity in the solid-state, in order to reduce dye aggregation, and thus obtain efficient pure blue photo- and electroluminescence. Accordingly, the new compounds displayed reasonably high spectral purity in both solution- and solid-states with average CIE coordinates of (0.160 ± 0.005, 0.029 ± 0.009) in solution and (0.152 ± 0.007, 0.126 ± 0.005) in solid-state. These compounds showed a systematic decrease in degree of crystallinity and intermolecular aggregation due to increasing steric hindrance, as revealed using powder X-ray diffraction analysis and spectroscopic studies. An organic light-emitting diode (OLED) prototype fabricated using compound B as the non-doped emissive layer displayed an external quantum efficiency (EQE) of 0.35 (±0.04)% and luminance 100 (±6) cd m(−2) at 5.5 V with an essentially pure blue electroluminescence corresponding to CIE coordinates of (0.1482, 0.1300). The highest EQE observed from this OLED prototype was 4.3 (±0.3)% at 3.5 V, and the highest luminance of 290 (±10) cd m(−2) at 7.5 V. These values were found comparable to characteristics of the best pure blue OLED devices based on simple fluorescent small-molecule organic chromophores.
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spelling pubmed-85884902021-11-13 Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs De Silva, Thenahandi Prasanthi Deepthika Youm, Sang Gil Fronczek, Frank R. Sahasrabudhe, Girija Nesterov, Evgueni E. Warner, Isiah M. Molecules Article Three novel small organic heterocyclic compounds: 2-(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound A), 1,3-di(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound B), and 1,3,6,8-tetra(1,2-diphenyl)-1H-benzimidazolepyrene (compound C) were synthesized and characterized for possible applications as blue OLED emitters. The specific molecular design targeted decreasing intermolecular aggregation and disrupting crystallinity in the solid-state, in order to reduce dye aggregation, and thus obtain efficient pure blue photo- and electroluminescence. Accordingly, the new compounds displayed reasonably high spectral purity in both solution- and solid-states with average CIE coordinates of (0.160 ± 0.005, 0.029 ± 0.009) in solution and (0.152 ± 0.007, 0.126 ± 0.005) in solid-state. These compounds showed a systematic decrease in degree of crystallinity and intermolecular aggregation due to increasing steric hindrance, as revealed using powder X-ray diffraction analysis and spectroscopic studies. An organic light-emitting diode (OLED) prototype fabricated using compound B as the non-doped emissive layer displayed an external quantum efficiency (EQE) of 0.35 (±0.04)% and luminance 100 (±6) cd m(−2) at 5.5 V with an essentially pure blue electroluminescence corresponding to CIE coordinates of (0.1482, 0.1300). The highest EQE observed from this OLED prototype was 4.3 (±0.3)% at 3.5 V, and the highest luminance of 290 (±10) cd m(−2) at 7.5 V. These values were found comparable to characteristics of the best pure blue OLED devices based on simple fluorescent small-molecule organic chromophores. MDPI 2021-10-28 /pmc/articles/PMC8588490/ /pubmed/34770936 http://dx.doi.org/10.3390/molecules26216523 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
De Silva, Thenahandi Prasanthi Deepthika
Youm, Sang Gil
Fronczek, Frank R.
Sahasrabudhe, Girija
Nesterov, Evgueni E.
Warner, Isiah M.
Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs
title Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs
title_full Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs
title_fullStr Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs
title_full_unstemmed Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs
title_short Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs
title_sort pyrene-benzimidazole derivatives as novel blue emitters for oleds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588490/
https://www.ncbi.nlm.nih.gov/pubmed/34770936
http://dx.doi.org/10.3390/molecules26216523
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