Abstract
Chirality is an important natural characteristic of organic molecules, and chiral organic molecules have shown extensive application in areas such as pharmaceutical development and material science. Benefiting from the ability to achieve circularly polarized luminescence (CPL), chiral luminescent materials have shown potential applications in anti-glare display, optical communication and, 3D display, etc. Due to the ability to harvest both singlet and triplet excitons by a fast reverse intersystem crossing process without involving noble metals, chiral thermally activated delayed fluorescence (TADF) materials with point chirality, axial chirality, planar chirality and helical chirality are regarded as the state-of-the-art materials for circularly polarized organic light-emitting diodes (CP-OLEDs). In recent years, the chiral TADF materials and CP-OLEDs have rapidly developed, but unfortunately, the dissymmetry factors (g) are far from the requirement of practical applications. The ideal emitters and devices should have both high efficiency and a g factor, or at least a balance between these two elements. This review gives an overview of recent progress in chiral TADF materials, with a particular focus on the chiral skeleton, CPL property and device performance. Furthermore, the molecular design concept, device structure and methods to improve the g factors of chiral materials and CP-OLEDs are also discussed.
References
Lin GQ, Li YM, Chan ASC. Principles and Applications of Asymmetric Synthesis. New York: Wiley & Sons, 2001
Gong ZL, Zhu X, Zhou Z, Zhang SW, Yang D, Zhao B, Zhang YP, Deng J, Cheng Y, Zheng YX, Zang SQ, Kuang H, Duan P, Yuan M, Chen CF, Zhao YS, Zhong YW, Tang BZ, Liu M. Sci China Chem, 2021, 64: 2060–2104
Yang X, Gao X, Zheng YX, Kuang H, Chen CF, Liu M, Duan P, Tang Z. CCS Chem, 2023, 5: 2760–2789
Zhao WL, Li M, Lu HY, Chen CF. Chem Commun, 2019, 55: 13793–13803
Sang Y, Han J, Zhao T, Duan P, Liu M. Adv Mater, 2020, 32: 1900110
Frédéric L, Desmarchelier A, Favereau L, Pieters G. Adv Funct Mater, 2021, 31: 2010281
Zhang DW, Li M, Chen CF. Chem Soc Rev, 2020, 49: 1331–1343
Han J, Guo S, Lu H, Liu S, Zhao Q, Huang W. Adv Opt Mater, 2018, 6: 1800538
Imagawa T, Hirata S, Totani K, Watanabe T, Vacha M. Chem Commun, 2015, 51: 13268–13271
Li M, Li S, Zhang D, Cai M, Duan L, Fung M, Chen C. Angew Chem Int Ed, 2018, 57: 2889–2893
Ni F, Huang CW, Tang Y, Chen Z, Wu Y, Xia S, Cao X, Hsu JH, Lee WK, Zheng K, Huang Z, Wu CC, Yang C. Mater Horiz, 2021, 8: 547–555
Yang Y, Li N, Miao J, Cao X, Ying A, Pan K, Lv X, Ni F, Huang Z, Gong S, Yang C. Angew Chem Int Ed, 2022, 61: e202202227
Wang Y, Li M, Teng J, Zhou H, Chen C. Adv Funct Mater, 2021, 31: 2106418
Wang Y, Li M, Teng J, Zhou H, Zhao W, Chen C. Angew Chem Int Ed, 2021, 60: 23619–23624
Yang SY, Wang YK, Peng CC, Wu ZG, Yuan S, Yu YJ, Li H, Wang TT, Li HC, Zheng YX, Jiang ZQ, Liao LS. J Am Chem Soc, 2020, 142: 17756–17765
Yang S, Feng Z, Fu Z, Zhang K, Chen S, Yu Y, Zou B, Wang K, Liao L, Jiang Z. Angew Chem Int Ed, 2022, 61: e202206861
Zhang Y, Liang X, Luo X, Song S, Li S, Wang Y, Mao Z, Xu W, Zheng Y, Zuo J, Pan Y. Angew Chem Int Ed, 2021, 60: 8435–8440
Zhang YP, Song SQ, Mao MX, Li CH, Zheng YX, Zuo JL. Sci China Chem, 2022, 65: 1347–1355
Luo X, Song S, Wu X, Yip C, Cai S, Zheng Y. Aggregate, 2023, e445
Feuillastre S, Pauton M, Gao L, Desmarchelier A, Riives AJ, Prim D, Tondelier D, Geffroy B, Muller G, Clavier G, Pieters G. J Am Chem Soc, 2016, 138: 3990–3993
Song F, Xu Z, Zhang Q, Zhao Z, Zhang H, Zhao W, Qiu Z, Qi C, Zhang H, Sung HHY, Williams ID, Lam JWY, Zhao Z, Qin A, Ma D, Tang BZ. Adv Funct Mater, 2018, 28: 1800051
Frédéric L, Desmarchelier A, Plais R, Lavnevich L, Muller G, Villafuerte C, Clavier G, Quesnel E, Racine B, Meunier-Della-Gatta S, Dognon J, Thuéry P, Crassous J, Favereau L, Pieters G. Adv Funct Mater, 2020, 30: 2004838
Xue P, Wang X, Wang W, Zhang J, Wang Z, Jin J, Zheng C, Li P, Xie G, Chen R. ACS Appl Mater Interfaces, 2021, 13: 47826–47834
Zhou L, Ni F, Li N, Wang K, Xie G, Yang C. Angew Chem Int Ed, 2022, 61: e202203844
Wu ZG, Han HB, Yan ZP, Luo XF, Wang Y, Zheng YX, Zuo JL, Pan Y. Adv Mater, 2019, 31: 1900524
Wu ZG, Yan ZP, Luo XF, Yuan L, Liang WQ, Wang Y, Zheng YX, Zuo JL, Pan Y. J Mater Chem C, 2019, 7: 7045–7052
Liu TT, Yan ZP, Hu JJ, Yuan L, Luo XF, Tu ZL, Zheng YX. ACS Appl Mater Interfaces, 2021, 13: 56413–56419
Xie F, Zhou J, Zeng X, An Z, Li Y, Han D, Duan P, Wu Z, Zheng Y, Tang J. Adv Opt Mater, 2021, 9: 2100017
Teng JM, Zhang DW, Wang YF, Chen CF. ACS Appl Mater Interfaces, 2022, 14: 1578–1586
Wang YF, Liu X, Zhu Y, Li M, Chen CF. J Mater Chem C, 2022, 10: 4805–4812
Sun BJ, Ding L, Wang XZ, Tu ZL, Fan J. Chem Eng J, 2023, 149: 146511
Xu Y, Wang Q, Cai X, Li C, Wang Y. Adv Mater, 2021, 33: 2100652
Yan ZP, Yuan L, Zhang Y, Mao MX, Liao XJ, Ni HX, Wang ZH, An Z, Zheng YX, Zuo JL. Adv Mater, 2022, 34: 2204253
Cho YJ, Jeon SK, Chin BD, Yu E, Lee JY. Angew Chem Int Ed, 2015, 54: 5201–5204
Wang Y, Zhang Y, Hu W, Quan Y, Li Y, Cheng Y. ACS Appl Mater Interfaces, 2019, 11: 26165–26173
Zhang Y, Li J, Quan Y, Ye S, Cheng Y. Chem Eur J, 2021, 27: 589–593
Zhao WL, Wang YF, Wan SP, Lu HY, Li M, Chen CF. CCS Chem, 2022, 4: 3540–3548
Qu L, Xiao H, Zhang B, Yang Q, Song J, Zhou X, Xu ZX, Xiang H. Chem Eng J, 2023, 471: 144709
Yan Z, Liu T, Wu R, Liang X, Li Z, Zhou L, Zheng Y, Zuo J. Adv Funct Mater, 2021, 31: 2103875
Li M, Wang Y, Zhang D, Duan L, Chen C. Angew Chem Int Ed, 2020, 59: 3500–3504
Tu Z, Yan Z, Liang X, Chen L, Wu Z, Wang Y, Zheng Y, Zuo J, Pan Y. Adv Sci, 2020, 7: 2000804
Tu Z, Lu J, Luo X, Hu J, Li S, Wang Y, Zheng Y, Zuo J, Pan Y. Adv Opt Mater, 2021, 9: 2100596
Wan SP, Zhao WL, Tan KK, Lu HY, Li M, Chen CF. Chem Eng J, 2023, 468: 143508
Sharma N, Spuling E, Mattern CM, Li W, Fuhr O, Tsuchiya Y, Adachi C, Bräse S, Samuel IDW, Zysman-Colman E. Chem Sci, 2019, 10: 6689–6696
Liao C, Zhang Y, Ye SH, Zheng WH. ACS Appl Mater Interfaces, 2021, 13: 25186–25192
Zhang DW, Teng JM, Wang YF, Han XN, Li M, Chen CF. Mater Horiz, 2021, 8: 3417–3423
Liao X, Pu D, Yuan L, Tong J, Xing S, Tu Z, Zuo J, Zheng W, Zheng Y. Angew Chem Int Ed, 2023, 62: e202217045
Wu X, Huang JW, Su BK, Wang S, Yuan L, Zheng WQ, Zhang H, Zheng YX, Zhu W, Chou PT. Adv Mater, 2022, 34: 2105080
Yang W, Li N, Miao J, Zhan L, Gong S, Huang Z, Yang C. CCS Chem, 2022, 4: 3463–3471
Wang Q, Yuan L, Qu C, Huang T, Song X, Xu Y, Zheng YX, Wang Y. AdvMater, 2023, 35: 2305125
Ye Z, Wu H, Xu Y, Hua T, Chen G, Chen Z, Yin X, Huang M, Xu K, Song X, Huang Z, Lv X, Miao J, Cao X, Yang C. AdvMater, 2024, 36: 2308314
Meng G, Zhou J, Han X, Zhao W, Zhang Y, Li M, Chen C, Zhang D, Duan L. Adv Mater, 2023, 35: 2307420
Yang SY, Zou SN, Kong FC, Liao XJ, Qu YK, Feng ZQ, Zheng YX, Jiang ZQ, Liao LS. Chem Commun, 2021, 57: 11041–11044
Yang SY, Tian QS, Liao XJ, Wu ZG, Shen WS, Yu YJ, Feng ZQ, Zheng YX, Jiang ZQ, Liao LS. J Mater Chem C, 2022, 10: 4393–4401
Qu C, Zhu Y, Liang L, Ye K, Zhang Y, Zhang H, Zhang Z, Duan L, Wang Y. Adv Opt Mater, 2023, 11: 2203030
Liang X, Liu T, Yan Z, Zhou Y, Su J, Luo X, Wu Z, Wang Y, Zheng Y, Zuo J. Angew Chem Int Ed, 2019, 58: 17220–17225
Lee DM, Song JW, Lee YJ, Yu CJ, Kim JH. Adv Mater, 2017, 29: 1700907
Wan L, Wade J, Salerno F, Arteaga O, Laidlaw B, Wang X, Penfold T, Fuchter MJ, Campbell AJ. ACS Nano, 2019, 13: 8099–8105
Qian G, Yang X, Wang X, Herod JD, Bruce DW, Wang S, Zhu W, Duan P, Wang Y. Adv Opt Mater, 2020, 8: 2000775
Chen Z, Zhong C, Han J, Miao J, Qi Y, Zou Y, Xie G, Gong S, Yang C. Adv Mater, 2022, 34: 2109147
Gu Q, Chen Z, Xie W, Qiu W, Peng X, Jiao Y, Li M, Liu Z, Sun G, Lu Y, Gan Y, Liu K, Zhao Z, Su S. Adv Opt Mater, 2022, 10: 2201793
Xu L, Liu H, Peng X, Shen P, Tang BZ, Zhao Z. Angew Chem Int Ed, 2023, 62: e202300492
Chen Z, Huang M, Zhong C, Cao X, Xie G, Gong S, Yang C. Adv Funct Mater, 2023, 33: 2215179
Zhao T, Han J, Duan P, Liu M. Acc Chem Res, 2020, 53: 1279–1292
Dong T, Wu Z, Li F, Wang J, Zheng Y, Yu L. Adv Opt Mater, 2022, 10: 2201105
Zinna F, Pasini M, Galeotti F, Botta C, Di Bari L, Giovanella U. Adv Funct Mater, 2017, 27: 1603719
Yan Z, Luo X, Liu W, Wu Z, Liang X, Liao K, Wang Y, Zheng Y, Zhou L, Zuo J, Pan Y, Zhang H. Chem Eur J, 2019, 25: 5672–5676
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This work was supported by the National Natural Science Foundation of China (92256304, U23A20593) and the Fundamental Research Funds for the Central Universities (020514380294).
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Yuan, L., Zhang, YP. & Zheng, YX. Chiral thermally activated delayed fluorescence materials for circularly polarized organic light-emitting diodes. Sci. China Chem. 67, 1097–1116 (2024). https://doi.org/10.1007/s11426-023-1910-1
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DOI: https://doi.org/10.1007/s11426-023-1910-1