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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2019
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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. |
format | Online Article Text |
id | pubmed-6360153 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
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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