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Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole

Carbazole (Cz) is the one of the most popular electron donors to develop thermally activated delayed fluorescence (TADF) emitters, but additional groups are generally required in the molecules to enhance the steric hindrance between Cz and electron acceptor segments. To address this issue, we replac...

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Autores principales: Cai, Jia-Lin, Liu, Wei, Wang, Kai, Chen, Jia-Xiong, Shi, Yi-Zhong, Zhang, Ming, Zheng, Cai-Jun, Tao, Si-Lu, Zhang, Xiao-Hong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6360153/
https://www.ncbi.nlm.nih.gov/pubmed/30746361
http://dx.doi.org/10.3389/fchem.2019.00017
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author Cai, Jia-Lin
Liu, Wei
Wang, Kai
Chen, Jia-Xiong
Shi, Yi-Zhong
Zhang, Ming
Zheng, Cai-Jun
Tao, Si-Lu
Zhang, Xiao-Hong
author_facet Cai, Jia-Lin
Liu, Wei
Wang, Kai
Chen, Jia-Xiong
Shi, Yi-Zhong
Zhang, Ming
Zheng, Cai-Jun
Tao, Si-Lu
Zhang, Xiao-Hong
author_sort Cai, Jia-Lin
collection PubMed
description Carbazole (Cz) is the one of the most popular electron donors to develop thermally activated delayed fluorescence (TADF) emitters, but additional groups are generally required in the molecules to enhance the steric hindrance between Cz and electron acceptor segments. To address this issue, we replaced Cz with its derivative 1,3,6,8-tetramethyl-carbazole (tMCz) to develop TADF emitters. Two novel compounds, 6-(4-(carbazol-9-yl)phenyl)-2,4-diphenylnicotinonitrile (CzPN) and 2,4-diphenyl-6-(4- (1,3,6,8-tetramethyl-carbazol-9-yl)phenyl) nicotinonitrile (tMCzPN) were designed and synthesized accordingly. With the same and simple molecular framework, tMCzPN successfully exhibits TADF behavior, while CzPN is a non-TADF fluorophor, as the additional steric hindrance of methyl groups leads to a more twisted structure of tMCzPN. In the organic light-emitting diodes (OLEDs), tMCzPN exhibits extremely high forward-viewing maximum external quantum efficiency of 26.0%, without any light out-coupling enhancement, which is significantly higher than that of 5.3% for CzPN. These results indicate that tMCzPN is an excellent TADF emitter and proves that tMCz is a more appropriate candidate than Cz to develop TADF emitters.
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spelling pubmed-63601532019-02-11 Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole Cai, Jia-Lin Liu, Wei Wang, Kai Chen, Jia-Xiong Shi, Yi-Zhong Zhang, Ming Zheng, Cai-Jun Tao, Si-Lu Zhang, Xiao-Hong Front Chem Chemistry Carbazole (Cz) is the one of the most popular electron donors to develop thermally activated delayed fluorescence (TADF) emitters, but additional groups are generally required in the molecules to enhance the steric hindrance between Cz and electron acceptor segments. To address this issue, we replaced Cz with its derivative 1,3,6,8-tetramethyl-carbazole (tMCz) to develop TADF emitters. Two novel compounds, 6-(4-(carbazol-9-yl)phenyl)-2,4-diphenylnicotinonitrile (CzPN) and 2,4-diphenyl-6-(4- (1,3,6,8-tetramethyl-carbazol-9-yl)phenyl) nicotinonitrile (tMCzPN) were designed and synthesized accordingly. With the same and simple molecular framework, tMCzPN successfully exhibits TADF behavior, while CzPN is a non-TADF fluorophor, as the additional steric hindrance of methyl groups leads to a more twisted structure of tMCzPN. In the organic light-emitting diodes (OLEDs), tMCzPN exhibits extremely high forward-viewing maximum external quantum efficiency of 26.0%, without any light out-coupling enhancement, which is significantly higher than that of 5.3% for CzPN. These results indicate that tMCzPN is an excellent TADF emitter and proves that tMCz is a more appropriate candidate than Cz to develop TADF emitters. Frontiers Media S.A. 2019-01-28 /pmc/articles/PMC6360153/ /pubmed/30746361 http://dx.doi.org/10.3389/fchem.2019.00017 Text en Copyright © 2019 Cai, Liu, Wang, Chen, Shi, Zhang, Zheng, Tao and Zhang. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Cai, Jia-Lin
Liu, Wei
Wang, Kai
Chen, Jia-Xiong
Shi, Yi-Zhong
Zhang, Ming
Zheng, Cai-Jun
Tao, Si-Lu
Zhang, Xiao-Hong
Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole
title Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole
title_full Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole
title_fullStr Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole
title_full_unstemmed Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole
title_short Highly Efficient Thermally Activated Delayed Fluorescence Emitter Developed by Replacing Carbazole With 1,3,6,8-Tetramethyl-Carbazole
title_sort highly efficient thermally activated delayed fluorescence emitter developed by replacing carbazole with 1,3,6,8-tetramethyl-carbazole
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6360153/
https://www.ncbi.nlm.nih.gov/pubmed/30746361
http://dx.doi.org/10.3389/fchem.2019.00017
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