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Synthesis and properties of quinazoline-based versatile exciplex-forming compounds.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-05-28 , DOI: 10.3762/bjoc.16.101
Rasa Keruckiene 1 , Simona Vekteryte 1 , Ervinas Urbonas 1 , Matas Guzauskas 1 , Eigirdas Skuodis 1 , Dmytro Volyniuk 1 , Juozas V Grazulevicius 1
Affiliation  

Three compounds, bearing a quinazoline unit as the acceptor core and carbazole, dimethyldihydroacridine, or phenothiazine donor moieties, were designed and synthesized in two steps including a facile copper-catalyzed cyclization and a nucleophilic aromatic substitution reaction. The photophysical properties of the compounds, based on theoretical calculations and experimental measurements, as well as the electrochemical and thermal properties, are discussed. The synthesized compounds form glasses with glass-transition temperatures ranging from 116 °C to 123 °C. The ionization potentials estimated by cyclic voltammetry of the derivatives were in the range of 5.22–5.87 eV. The 3,6-di-tert-butylcarbazole-substituted quinazoline-based compound forms a sky-blue emitting exciplex in solid mixture with the acceptor 2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine as well as an orange emitting exciplex with the donor 4,4′,4″-tris[3-methylphenyl(phenyl)amino]triphenylamine. A white OLED based on these versatile exciplex systems with a relatively high maximum brightness of 3030 cd/m2 and an external quantum efficiency of 0.5% was fabricated.

中文翻译:


基于喹唑啉的多功能激基复合物形成化合物的合成和性能。



设计并分两步合成了三种带有喹唑啉单元作为受体核心和咔唑、二甲基二氢吖啶或吩噻嗪供体部分的化合物,包括简单的铜催化环化和亲核芳香族取代反应。基于理论计算和实验测量,讨论了化合物的光物理性质以及电化学和热性质。合成的化合物形成玻璃化转变温度为 116 °C 至 123 °C 的玻璃。通过循环伏安法估计衍生物的电离势在 5.22-5.87 eV 范围内。 3,6-二叔丁基咔唑取代的喹唑啉基化合物与受体2,4,6-三[3-(二苯基次膦基)苯基]-1,3,5在固体混合物中形成天蓝色发射激基复合物-三嗪以及带有供体 4,4',4"-三[3-甲基苯基(苯基)氨基]三苯胺的橙色发射激基复合物。基于这些通用激基复合物系统的白色OLED被制造出来,具有相对较高的最大亮度3030cd/m 2和0.5%的外量子效率。
更新日期:2020-05-28
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