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Chiral multiple-resonance thermally activated delayed fluorescence materials based on chiral spiro-axis skeleton for efficient circularly polarized electroluminescence

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Science China Chemistry 2024年第7期67卷 2257-2264页

作者： Shi-Quan Song Xiao Han Zhong-Zhong Huo Ching-Fai Yip Xian-Fang Hong Meng-Ning Ding You-Xuan Zheng State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China Key Laboratory of Mesoscopic Chemistry of Ministry of Education School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Chiral luminescence materials have potential applications in the field of three-dimensional displays due to their circularly polarized luminescence(CPL)***,the further development of circularly polarized organic light-emitting diodes(CP-OLEDs)needs to meet the requirements of high efficiency,high color purity,low cost,and high dissymmetry factor(gPLor gEL),chiral multiple resonance thermally activated delayed fluorescence(MR-TADF)materials are considered as candidates in these ***,based on a pair of chiral spirofluorene precursors,two pairs of high-performance chiral MR-TADF emitters((R/S)-p-Spiro-DtBuCzB and(R/S)-m-Spiro-DtBuCzB)are developed,which exhibit strong emissions peaking at 491 and 502 nm in toluene with full-width at half-maximum values of 25 and 33 nm,*** addition,small singlet–triplet energy gaps of 0.15 and 0.10 eV with high absolute photoluminescence efficiencies of 95.0%and 96.7%are observed for p-Spiro-DtBuCzB and m-Spiro-DtBuCzB molecules,*** based on p-Spiro-DtBuCzB and m-Spiro-DtBuCzB display high maximum external quantum efficiencies of 29.6%and 33.8%,*** importantly,CP-OLEDs present symmetric circularly polarized electroluminescence spectra with|gEL|factors of 3.36×10^(-4)and 7.66×10^(-4)for devices based on(R/S)-p-Spiro-DtBuCzB and(R/S)-m-Spiro-DtBuCzB enantiomers,respectively.

关键词： chiral spiro-axis skeleton-based material multiple resonance thermally activated delayed fluorescence circularly polarized electroluminescence dissymmetry factor external quantum efficiency

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Research Advances in Helicene Structure-Based Chiral Luminescent Materials and Their circularly polarized electroluminescence

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Chinese Journal of Structural Chemistry 2022年第12期41卷 70-79页

作者： Xu-Feng Luo Jie He Yang Wang Hong Dai Zheng-Guang Wu School of Chemistry and Chemical Engineering Nantong UniversityNantongJiangsu 226019China College of Material Science and Chemical Engineering Ningbo University of TechnologyNingboZhejiang 315211China

Benefited from direct generation of circularly polarized(CP) emission with tunable colors, high efficiencies and facile device architectures, CP organic light-emitting diodes(CP-OLEDs) have attracted great attention and are expected to meet industrial applications. Particularly, CP electroluminescence(CPEL) originated from CP-OLEDs has wide potential applications in 3D displays, optical information storage, quantum communication, and biological sensors. The diverse design strategies of chiral luminescent materials for CP-OLEDs, including small organic emitters, lanthanide and transition-metal complexes and conjugated polymers, have been extensively explored. Helicene with twisted extended π-conjugated molecular structure could exhibit special helical chirality and excellent circularly polarized luminescence properties, which has been employed as the ingenious chirality core for constructing efficient chiral luminescent materials. In addition, significant improvements have been made in terms of CP photoluminescence research, however, the development of CPEL with more application prospects in optoelectronic technology still lags behind. In this review, we systematically summarize the recent advances in chiral luminescent materials based on helicene structure and their CPEL properties, including helicene-based chiral fluorescence molecules, transition metal complexes and thermally activated delayed fluorescence molecules, and discuss current challenges and future perspectives for this hot research field. We believe this progress report will provide a promising perspective of OLEDs based on helicene emitters with CPEL properties for extensive researchers, including chemical, physical and material scientists in different disciplinary fields and attract them to this rapidly developing field.

关键词： helicene circularly polarized luminescence circularly polarized electroluminescence chiral luminescent material thermally activated delayed fluorescence

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Efficient circularly polarized photoluminescence and electroluminescence of chiral spiro-skeleton-based thermally activated delayed fluorescence molecules

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Science China Chemistry 2022年第7期65卷 1347-1355页

作者： Yi-Pin Zhang Shi-Quan Song Meng-Xi Mao Cheng-Hui Li You-Xuan Zheng Jing-Lin Zuo State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China MaAnShan High-Tech Research Institute of Nanjing University Maanshan 238200China

Chiral thermally activated delayed fluorescence(TADF) molecules showing circularly polarized luminescence(CPL) have great potential in 3D displays. However, the relationships among CPL property, device performance and molecule structure are still not clear. In this article, we develop a strategy to promote dissymmetry factors without sacrifice in device performance and study the impact of molecule structures towards CPL property. Three novel TADF enantiomers are synthesized and studied.(R/S)-SCN with diminutive cyano group as an acceptor shows dissymmetry factor |gPL| ≈ 1.4×10^(-3) and noticeable organic light-emitting diode(OLED) performances with a maximum external quantum efficiency(EQEmax) of 23.0%. For(R/S)-SPHCN, the prolonged electron withdrawing group benzonitrile enhances |gPL| up to 3.6×10^(-3) with decreased device EQEmaxof 15.4%. By further replacing benzonitrile with(trifluoromethyl)pyridine, the enantiomers of(R/S)-SCFPY show similar |gPL| factors of 3.5×10^(-3) and device EQE_(max)up to 23.3%, which represents the highest efficiency among sprio-type TADF materials based OLEDs. Furthermore, the OLEDs also show obvious circularly polarized electroluminescence with gELfactors of-1.4/1.8×10^(-3),-3.6/3.6×10^(-3) and-3.7/3.6×10^(-3), respectively. These results indecate by delicate functional group engineering, high g factor can be achieved while maintaining decent device performances. Besides,(R/S)-SCFPY represents an impressive TADF emitter, which shows promoted g factor and recorded high device EQE_(max)among similar molecules.

关键词： chiral spiro-skeleton thermally activated delayed fluorescence circularly polarized photoluminescence circularly polarized electroluminescence dissymmetry factor

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Recent Progress of circularly polarized Luminescence Materials from Chinese Perspectives

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CCS Chemistry 2023年第12期5卷 2760-2789页

作者： Xuefeng Yang Xiaoqing Gao You-Xuan Zheng Hua Kuang Chuan-Feng Chen Minghua Liu Pengfei Duan Zhiyong Tang CAS Key Laboratory of Nanosystem and Hierarchical Fabrication National Center for Nanoscience and Technology(NCNST)Beijing 100190 Wenzhou Key Laboratory of Biophysics Wenzhou InstituteUniversity of Chinese Academy of SciencesWenzhouZhejiang 325000 State Key Laboratory of Coordination Chemistry School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023 International Joint Research Laboratory for Biointerface and Biodetection State Key Lab of Food Science and TechnologySchool of Food Science and TechnologyJiangnan UniversityWuxi 214122 Beijing National Laboratory of Molecular Sciences and CAS Key Laboratory of Colloid Interface and ThermodynamicsInstitute of ChemistryChinese Academy of SciencesBeijing 100190

The research on circularly polarized luminescence(CPL)has garnered significant attention in recent years due to its many potential *** aspect of this research involves the pursuit of chiral materials that posess both high luminescence efficiency and dissymmetry *** investigation of CPL behavior is of paramount importance because the structural information of chiral luminescent systems in the excited state can be *** objective of this review is to offer a comprehensive overview of the latest advancements in the CPL research field,with a particular focus on the development of chiral emissive materials,including organic,inorganic,and hybrid ***,this review outlines the recent applications of these materials in areas such as displays,photoelectric devices,anticounterfeiting measures,and ***,we highlight the primary challenges and potential prospects of CPL *** aspiration is that this endeavor will contribute new perspectives and insights that further advancements in related research fields.

关键词： circularly polarized luminescence circularly polarized electroluminescence circular dichroism optoelectronic materials excited-state chirality chirality

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