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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

Molecular self-induced configuration for improving dissymmetry factors in tetradentate platinum(Ⅱ) enantiomers cycloaddition

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Chinese Chemical Letters 2022年第3期33卷 1459-1462页

作者： Li Yuan Qian-Jun Ding Zhen-Long Tu Xiang-Ji Liao Xu-Feng Luo Zhi-Ping Yan Zheng-Guang Wu You-Xuan Zheng State Key Laboratory of Coordination Chemistry School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China Nantong Key Lab of Intelligent and New Energy Materials College of Chemistry and Chemical EngineeringNantong UniversityNantong 226019China

Two pairs of Pt(Ⅱ) enantiomers((RR)/(SS)-Py Pt,((RR)/(SS)-Py: N,N’-(1,2-diphenylethane-1,2-diyl)dipicolinamide;(RR)-P/M-QPt,((RR)/(SS)-Q: N,N’-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(quinoline-2-carboxamide)) were synthesized, respectively, with good circularly polarized luminescence(CPL) and tunable dissymmetry factors(g) by molecular self-induction with(RR)/(SS)-1,2-diphenylethane-1,2-diamine as carbon chiral sources. In the(RR)-P-QPt and(SS)-M-QPt, specific P-and M-configurations were effectively induced from intrinsic chiral carbon centres(R or S), ingeniously avoiding the racemic mixture formation and chiral separation. Furthermore, the chirality originating from both chiral carbon centres and helicene-like structure improves the g factor significantly, which provides a new molecular design strategy for chiral Pt(II) enantiomers with good CPL properties.

关键词： Pt(Ⅱ)enantiomer Circularly polarized luminescence dissymmetry factor Molecular self-induction Helicene-like structure

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