Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-Diodes
New fluorescent D-A-D dyes containing 9-(<i>p</i>-tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a donor unit and 2,1,3-benzochalcogenadiazoles as an electron-withdrawing group were synthesized. The photoluminescent and electroluminescent properties of novel dyes for f...
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| Format: | Article |
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MDPI AG
2021-05-01
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| Online Access: | https://www.mdpi.com/1420-3049/26/10/2872 |
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| author | Vladislav M. Korshunov Maxim S. Mikhailov Timofey N. Chmovzh Andrey A. Vashchenko Nikita S. Gudim Lyudmila V. Mikhalchenko Ilya V. Taydakov Oleg A. Rakitin |
| author_facet | Vladislav M. Korshunov Maxim S. Mikhailov Timofey N. Chmovzh Andrey A. Vashchenko Nikita S. Gudim Lyudmila V. Mikhalchenko Ilya V. Taydakov Oleg A. Rakitin |
| author_sort | Vladislav M. Korshunov |
| collection | DOAJ |
| description | New fluorescent D-A-D dyes containing 9-(<i>p</i>-tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a donor unit and 2,1,3-benzochalcogenadiazoles as an electron-withdrawing group were synthesized. The photoluminescent and electroluminescent properties of novel dyes for fluorescent OLED application were investigated. It was demonstrated that the replacement of lightweight heteroatoms by heavier ones enables the fine tuning of the maximum emission without significantly reducing the luminescence quantum yield. The maximum quantum yield value of 62.6% for derivatives based on 2,1,3-benzoxadiazole (<b>1a</b>) in cyclohexane was achieved. Two devices with the architecture of glass/ITO/PEDOT-PSS/poly-TPD/EML/TPBi/LiF/Al (EML = emitting layer) were fabricated to check the suitability of the synthesized compounds as a single active emission layer in OLED. These OLEDs exhibited clear red electroluminescence of the dyes with the maximum current efficiency of 0.85 Cd/A. |
| first_indexed | 2024-03-10T11:28:56Z |
| format | Article |
| id | doaj.art-94f15e797da54a3e95b9786e76a1a513 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:28:56Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-94f15e797da54a3e95b9786e76a1a5132023-11-21T19:24:23ZengMDPI AGMolecules1420-30492021-05-012610287210.3390/molecules26102872Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-DiodesVladislav M. Korshunov0Maxim S. Mikhailov1Timofey N. Chmovzh2Andrey A. Vashchenko3Nikita S. Gudim4Lyudmila V. Mikhalchenko5Ilya V. Taydakov6Oleg A. Rakitin7P. N. Lebedev Physical Institute of the Russian Academy of Sciences, 53 Leninskiy Prospect, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 119991 Moscow, RussiaP. N. Lebedev Physical Institute of the Russian Academy of Sciences, 53 Leninskiy Prospect, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 119991 Moscow, RussiaP. N. Lebedev Physical Institute of the Russian Academy of Sciences, 53 Leninskiy Prospect, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 119991 Moscow, RussiaNew fluorescent D-A-D dyes containing 9-(<i>p</i>-tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a donor unit and 2,1,3-benzochalcogenadiazoles as an electron-withdrawing group were synthesized. The photoluminescent and electroluminescent properties of novel dyes for fluorescent OLED application were investigated. It was demonstrated that the replacement of lightweight heteroatoms by heavier ones enables the fine tuning of the maximum emission without significantly reducing the luminescence quantum yield. The maximum quantum yield value of 62.6% for derivatives based on 2,1,3-benzoxadiazole (<b>1a</b>) in cyclohexane was achieved. Two devices with the architecture of glass/ITO/PEDOT-PSS/poly-TPD/EML/TPBi/LiF/Al (EML = emitting layer) were fabricated to check the suitability of the synthesized compounds as a single active emission layer in OLED. These OLEDs exhibited clear red electroluminescence of the dyes with the maximum current efficiency of 0.85 Cd/A.https://www.mdpi.com/1420-3049/26/10/28722,1,3-benzochalcogenadiazoles2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazoleD-A-D dyesluminescenceOLEDs |
| spellingShingle | Vladislav M. Korshunov Maxim S. Mikhailov Timofey N. Chmovzh Andrey A. Vashchenko Nikita S. Gudim Lyudmila V. Mikhalchenko Ilya V. Taydakov Oleg A. Rakitin Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-Diodes Molecules 2,1,3-benzochalcogenadiazoles 2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole D-A-D dyes luminescence OLEDs |
| title | Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-Diodes |
| title_full | Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-Diodes |
| title_fullStr | Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-Diodes |
| title_full_unstemmed | Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-Diodes |
| title_short | Novel D-A-D Fluorescent Dyes Based on 9-(<i>p</i>-Tolyl)-2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole as a Donor Unit for Solution-Processed Organic Light-Emitting-Diodes |
| title_sort | novel d a d fluorescent dyes based on 9 i p i tolyl 2 3 4 4a 9 9a hexahydro 1 i h i carbazole as a donor unit for solution processed organic light emitting diodes |
| topic | 2,1,3-benzochalcogenadiazoles 2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole D-A-D dyes luminescence OLEDs |
| url | https://www.mdpi.com/1420-3049/26/10/2872 |
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