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一种基于萘并噻二唑作为发光体的深红色荧光团,具有杂化的局域和电荷转移以及双极性传输特性,用于电致发光器件。

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices.

作者信息

Arunlimsawat Suangsiri, Funchien Patteera, Chasing Pongsakorn, Saenubol Atthapon, Sudyoadsuk Taweesak, Promarak Vinich

机构信息

Department of Materials Science and Engineering, School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology, Wangchan, Rayong 21210, Thailand.

Frontier Research Center, Vidyasirimedhi Institute of Science and Technology, Wangchan, Rayong 21210, Thailand.

出版信息

Beilstein J Org Chem. 2023 Nov 3;19:1664-1676. doi: 10.3762/bjoc.19.122. eCollection 2023.

DOI:10.3762/bjoc.19.122
PMID:37942020
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10630680/
Abstract

Herein, we report the synthesis and characterization of an efficient ambipolar charge-carrier-transporting deep-red fluorophore () based on a donor-acceptor-donor (D-A-D)-type molecule and its application as a non-doped emitter in an organic light-emitting diode (OLED). The fluorophore contains naphtho[2,3-][1,2,5]thiadiazole (Nz) as a strong acceptor unit symmetrically functionalized with -(4-(1,2,2-triphenylvinyl)phenyl)carbazole as a donor and aggregation-induced emission (AIE) luminogen. The experimental (solvatochromic and emission in THF/water mixtures studies) and theoretical investigations prove that retains cooperative hybridized local and charge transfer (HLCT) and weak AIE features. Thanks to its D-A-D-type structure with a proper twist angle between the D and A units, a strong electron deficiency of the Nz unit, and electron-donating and hole-transporting natures of carbazole, exhibits a strong deep red emission (λ = 648 nm) with a high fluorescence quantum yield of 96%, outstanding thermal property ( = 236 °C), and ambipolar charge-carrier-transporting property with a decent balance of mobility of electrons (1.50 × 10 cm V s) and holes (4.42 × 10 cm V s). is successfully employed as a non-doped emitter in an OLED which displays deep red electroluminescent emission peaked at 659 nm with CIE coordinates of (0.664, 0.335)), an EQE of 3.32% and exciton utilization efficiency (EUE) of 47%.

摘要

在此,我们报道了一种基于供体-受体-供体(D-A-D)型分子的高效双极性电荷载流子传输深红色荧光团()的合成与表征,以及其作为非掺杂发光体在有机发光二极管(OLED)中的应用。该荧光团包含萘并[2,3-][1,2,5]噻二唑(Nz)作为强受体单元,对称地官能化有作为供体的-(4-(1,2,2-三苯基乙烯基)苯基)咔唑和聚集诱导发光(AIE)发光剂。实验(在四氢呋喃/水混合物中的溶剂化显色和发射研究)和理论研究证明,保留了协同杂化局域和电荷转移(HLCT)以及弱AIE特性。由于其D-A-D型结构,在D和A单元之间具有合适的扭曲角,Nz单元具有很强的电子缺欠性,以及咔唑的供电子和空穴传输性质,表现出强烈的深红色发射(λ = 648 nm),荧光量子产率高达96%,出色的热性能(= 236 °C),以及双极性电荷载流子传输性质,电子迁移率(1.50 × 10 cm V s)和空穴迁移率(4.42 × 10 cm V s)有良好的平衡。成功地用作OLED中的非掺杂发光体,该OLED显示出在659 nm处达到峰值的深红色电致发光发射,CIE坐标为(0.664, 0.335),外量子效率为3.32%,激子利用效率(EUE)为47%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/6cc1aed674ad/Beilstein_J_Org_Chem-19-1664-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/c61c04b66ca0/Beilstein_J_Org_Chem-19-1664-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/291be3fe12f9/Beilstein_J_Org_Chem-19-1664-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/43cd90cabe48/Beilstein_J_Org_Chem-19-1664-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/f2f089e7dafc/Beilstein_J_Org_Chem-19-1664-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/ff721e2d9249/Beilstein_J_Org_Chem-19-1664-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/26c6f5736aa8/Beilstein_J_Org_Chem-19-1664-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/760427ab6f54/Beilstein_J_Org_Chem-19-1664-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/6cc1aed674ad/Beilstein_J_Org_Chem-19-1664-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/c61c04b66ca0/Beilstein_J_Org_Chem-19-1664-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/291be3fe12f9/Beilstein_J_Org_Chem-19-1664-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/43cd90cabe48/Beilstein_J_Org_Chem-19-1664-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/f2f089e7dafc/Beilstein_J_Org_Chem-19-1664-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/ff721e2d9249/Beilstein_J_Org_Chem-19-1664-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/26c6f5736aa8/Beilstein_J_Org_Chem-19-1664-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/760427ab6f54/Beilstein_J_Org_Chem-19-1664-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edde/10630680/6cc1aed674ad/Beilstein_J_Org_Chem-19-1664-g008.jpg

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