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2021 , Vol. 79 >Issue 11: 1401 - 1408

DOI: https://doi.org/10.6023/A21070355

研究论文

基于八氢联萘酚的大位阻手性发光材料构建及光电性质研究

  • 梁志鹏 ,
  • 唐瑞 ,
  • 邱雨晨 ,
  • 王阳 ,
  • 陆洪彬 ,
  • 吴正光
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  • 南通大学化学化工学院 南通 226019

收稿日期: 2021-07-31

  网络出版日期: 2021-09-13

基金资助

项目受国家自然科学基金(22005158); 项目受国家自然科学基金(22072068)

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Construction and Properties of Octahydrobinaphthol-based Chiral Luminescent Materials with Large Steric Hindrance

  • Zhi-Peng Liang ,
  • Rui Tang ,
  • Yu-Chen Qiu ,
  • Yang Wang ,
  • Hongbin Lu ,
  • Zheng-Guang Wu
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  • School of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China
* E-mail: ;
* E-mail: ;

Received date: 2021-07-31

  Online published: 2021-09-13

Supported by

National Natural Science Foundation of China(22005158); National Natural Science Foundation of China(22072068)

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摘要

以手性发光材料为发光中心制备能够直接发射出圆偏振电致发光(circularly polarized electroluminescence, CPEL)的器件, 即CP-organic light-emitting diode (CP-OLED), 在3D显示领域有极大的应用前景. 本工作设计了基于八氢联萘酚的手性热激活延迟荧光材料(S/R)-OBN-tBuCz, 八氢联萘酚作为有效的手性源, 而叔丁基咔唑取代的氰基苯作为高效发光部分. 八氢联萘酚外围较多的氢原子以及较大的叔丁基可以有效增加手性发光分子的空间位阻, 降低堆积效应, 抑制浓度淬灭, 有效提升器件的发光效率. 所合成的手性发光材料展现出明亮的绿光发射(523 nm)、高的荧光量子产率(85.2%)、较小的单线态-三线态能级差ΔEST (0.05 eV)和优秀的热稳定性. 圆二色(CD)与圆偏振发光(CPL)光谱显示出明显的对称圆偏振发光信号, 且溶液中的gPL为+8.6×10-4和–6.5×10-4. 基于(S/R)-OBN-tBuCz的电致发光器件表现出优异性能: 起亮电压为3.9 V, 最大亮度为27709 cd•m-2, 最大电流效率为43.8 cd•A-1, 最大功率效率为33.5 lm•W-1, 最大外量子效率为12.4%, 效率滚降很低, 并显示出明显的圆偏振电致发光信号, gEL分别为+1.57×10-3和–0.90×10-3. 大位阻手性发光材料的设计有助于实现高效的CP-OLED, 该研究能促进手性发光材料及圆偏振电致发光器件等相关研究领域的发展.

关键词： 手性发光材料; 圆偏振发光; 八氢联萘酚; 大位阻; 圆偏振有机发光二极管

本文引用格式

梁志鹏 , 唐瑞 , 邱雨晨 , 王阳 , 陆洪彬 , 吴正光 . 基于八氢联萘酚的大位阻手性发光材料构建及光电性质研究[J]. 化学学报, 2021 , 79(11) : 1401 -1408 . DOI: 10.6023/A21070355

Abstract

Using chiral luminescent material as the emitting core in organic light-emitting diodes (OLEDs) would make these devices possess circularly polarized electroluminescence (CPEL) performance, namely CP-OLEDs, which are of great value for facilitating the development of the next generation of display technologies, especially for implementing real 3D display. In this study, a pair of octahydrobinaphthol (OBN)-based thermally activated delayed fluorescence (TADF) materials, (S/R)-OBN-tBuCz, are developed by ingeniously merging a chiral source (OBN) and a luminophore skeleton (tert-butylcarbazole cyanobenzene). The peripheral sixteen hydrogen atoms in cyclohexane part of OBN unit and the larger tertiary butyl group could effectively increase the steric hindrance of chiral luminescence molecules, reduce the intermolecular stacking effect and inhibit concentration quenching, for effectively improving the luminescence efficiency of the devices. The synthesized chiral luminescent materials exhibit bright green light emission (523 nm), high photoluminescence quantum yield (85.2%), a small ΔEST of 0.05 eV with TADF property as well as excellent thermal stability. The chiroptical properties of (S/R)-OBN-tBuCz enantiomers in the ground and excited states are investigated by circular dichroism (CD) and circularly polarized luminescence (CPL) spectra, and the strong symmetrically circularly polarized luminescent signals with gPL of +8.6×10-4 and –6.5×10-4 in toluene solution are observed for (S)-OBN-tBuCz and (R)-OBN-tBuCz, respectively, indicating that the chirality is successfully induced into the TADF skeleton through chirality transmitting of OBN unit. Considering the efficient TADF and CPL properties, the enantiomers are employed as chiral emitters for fabricating CP-OLEDs. The electroluminescent devices based on (S/R)-OBN-tBuCz exhibit decent performances with the turn-on voltage of 3.9 V, the maximum brightness of 27709 cd•m-2, the maximum current efficiency of 43.8 cd•A-1, the maximum power efficiency of 33.5 lm•W-1, the maximum external quantum efficiency of 12.4% and low efficiency roll-off as well as obvious circularly polarized electroluminescence signals with gEL of +1.57×10-3 and –0.90×10-3, respectively. The design strategy of rationally merging chiral source and TADF skeleton can promote the development of chiral luminescent materials and circularly polarized electroluminescent devices.

Key words： chiral luminescent material; circularly polarized luminescence; octahydrobinaphthol; large steric hindrance; circularly polarized organic light-emitting diodes

参考文献

[1]
(a) Trung T. Q.; Lee N. E. Adv. Mater. 2017, 29, 1603167.
[1]
(b) Chen S.; Dai J.; Zhou K.; Luo Y.; Su S.; Pu X.; Huang Y.; Lu Z. Acta Chim. Sinica 2017, 75, 367. (in Chinese)
[1]
( 陈仕琦, 代军, 周凯峰, 罗艳菊, 苏仕健, 蒲雪梅, 黄艳, 卢志云, 化学学报, 2017, 75, 367.)
[1]
(c) Kim J. H.; Yun J. H.; Lee J. Y. Adv. Opt. Mater. 2018, 6, 1800255.
[1]
(d) Lin D.; Song S.; Chen Z.; Guo P.; Chen J.; Shi H.; Mai Y.; Song H. Chin. J. Org. Chem. 2018, 38, 103. (in Chinese)
[1]
林丹燕, 宋森川, 陈智勇, 郭鹏然, 陈江韩, 史华红, 麦裕良, 宋化灿, 有机化学, 2018, 38, 103).
[1]
(e) Zhou W.; Liu Z.; Wang Z.; Hu S.; Liang A. Chin. J. Org. Chem. 2019, 39, 1214. (in Chinese)
[1]
周文静, 刘志谦, 王志平, 胡斯帆, 梁爱辉, 有机化学, 2019, 39, 1214).
[1]
(f) He X.; Xiao Y.; Yuan X.; Ye S.; Jiang H. Chin. J. Org. Chem. 2019, 39, 761. (in Chinese)
[1]
何煦, 肖燏萍, 袁鑫磊, 叶尚辉, 姜鸿基, 有机化学, 2019, 39, 761).
[1]
(g) Godumala M.; Choi S.; Cho M. J.; Choi D. H. J. Mater. Chem. C 2019, 7, 2172.
[1]
(h) Wu Z.-G.; Yang B.; Qiu Y.-C.; Wang Y.; Dai H.; Zheng Y.-X.; Wang Y.; Hu L.; Pan Y. Dalton Trans. 2021, 50, 3887.
[1]
(i) Tang M.-C.; Chan M.-Y.; Yam V. W.-. W. Chem. Rev. 2021, 121, 7249.
[1]
(j) Cao L.; Zhu Z.-Q.; Klimes K.; Li J. Adv. Mater. 2021, 33, 2101423.
[1]
(k) Chen Y.-K.; Jayakumar J.; Hsieh C.-M.; Wu T.-L.; Liao C.-C.; Pandidurai J.; Ko C.-L.; Hung W.-Y.; Cheng C.-H. Adv. Mater. 2021, 2008032.
[2]
(a) Schadt M. Liq. Cryst. 1989, 5, 57.
[2]
(b) Zhang Y.; Schuster G. B. J. Org. Chem. 1995, 60, 7192.
[2]
(c) Jager W. F.; Lange B. D.; Feringa B. L. Science 1996, 273, 1686.
[2]
(d) Wang C.; Fei H.; Qiu Y.; Yang Y.; Wei Z.; Tian Y.; Chen Y.; Zhao Y. Appl. Phys. Lett. 1999, 74, 19.
[2]
(e) Sherson J.; Krauter H.; Olsson R.; Julasgaard B.; Hammerer K.; Cirac I.; Polzik E. Nature 2006, 443, 557.
[2]
(f) Relaix S.; Bourgerette C.; Mitov M. Appl. Phys. Lett. 2006, 89, 251907.
[2]
(g) Farshchi R.; Ramsteiner M.; Herfort J.; Tahraoui A.; Grahn H. T. Appl. Phys. Lett. 2011, 98, 162508.
[2]
(h) Heffern M. C.; Matosziuk L. M.; Meade T. J. Chem. Rev. 2014, 114, 4496.
[2]
(i) Sánchez-Carnerero E.; Agarrabeitia A.; Moreno F.; Maroto B.; Muller G.; Ortiz M.; de la Moya S. Chem. Eur. J. 2015, 21, 13488.
[2]
(j) Kumar J.; Nakashima T.; Kawai T. J. Phys. Chem. Lett. 2015, 6, 3445.
[2]
(k) Yan J.; Ota F.; San Jose B. A.; Akagi K. Adv. Funct. Mater. 2017, 27, 1604529.
[2]
(l) Chen N.; Yan B. Molecules 2018, 23, 3376.
[2]
(m) Ma J.-L.; Peng Q.; Zhao C.-H. Chem. Eur. J. 2019, 25, 15441.
[2]
(n) Sang Y.; Han J.; Zhao T.; Duan P.; Liu M. Adv. Mater. 2019, 1900110.
[2]
(o) Zhao W.-L.; Li M.; Lu H.-Y.; Chen C.-F. Chem. Commun. 2019, 55, 13793.
[2]
(p) Song F.; Zhao Z.; Liu Z.; Lam J. W. Y.; Tang B. Z. J. Mater. Chem. C 2020, 8, 3284.
[3]
(a) Han J.; Guo S.; Lu H.; Liu S.; Zhao Q.; Huang W. Adv. Optical Mater. 2018, 6, 1800538.
[3]
(b) Zhang D.-W.; Li M.; Chen C.-F. Chem. Soc. Rev. 2020, 49, 1331.
[3]
(c) Frédéric L.; Desmarchelier A.; Favereau L.; Pieters G. Adv. Funct. Mater. 2021, 31, 2010281.
[3]
(d) Li X.; Xie Y.; Li Z. Adv. Photonics Res. 2021, 2, 2000136.
[4]
(a) Peeters E.; Christiaans M.; Janssen R.; Schoo H.; Dekkers H.; Meijer E. W. J. Am. Chem. Soc. 1997, 119, 9909.
[4]
(b) Oda M.; Nothofer H.-G.; Lieser G.; Scherf U.; Meskers S. C. J.; Neher D. Adv. Mater. 2000, 12, 362.
[4]
(c) Oda M.; Nothofer H.-G.; Scherf U.; Sunjic V.; Richter D.; Regenstein W.; Neher D. Macromolecules 2002, 35, 6792.
[4]
(d) Geng Y.; Trajkovska A.; Culligan S. W.; Ou J. J.; Philip Chen H. M.; Katsis D.; Chen S. H. J. Am. Chem. Soc. 2003, 125, 14032.
[4]
(e) Yang Y.; Costa R. C. D.; Smilgies D. M.; Campbell A. J.; Fuchter M. J. Adv. Mater. 2013, 25, 2624.
[4]
(f) Lee D. M.; Song J. W.; Lee Y. J.; Yu C. J.; Kim J. H. Adv. Mater. 2017, 29, 1700907.
[4]
(g) Nuzzo D. D.; Kulkarni C.; Zhao B.; Smolinsky E.; Tassinari F.; Meskers S. C. J.; Naaman R.; Meijer E. W.; Friend R. H. ACS Nano 2017, 11, 12713.
[4]
(h) Yang L.; Zhang Y.; Zhang X.; Li N.; Quan Y.; Cheng Y. Chem. Commun. 2018, 54, 9663.
[4]
(i) Kulkarni C.; van Son M. H. C.; Nuzzo D. D.; Meskers S. C. J.; Palmans A. R. A.; Meijer E. W. Chem. Mater. 2019, 31, 6633.
[5]
(a) Lunkley J. L.; Shirotani D.; Yamanar K.; Kaizaki S.; Muller G. Inorg. Chem. 2011, 50, 12724.
[5]
(b) Zinna F.; Bari L. D. Chirality 2015, 27, 1.
[5]
(c) Zinna F.; Giovanella U.; Bari L. D. Adv. Mater. 2015, 27, 1791.
[5]
(d) Zinna F.; Pasini M.; Galeotti F.; Botta C.; Bari L. D.; Giovanella U. Adv. Funct. Mater. 2017, 27, 1603719.
[5]
(e) Li T. Y.; Jing Y. M.; Liu X.; Zhao Y.; Shi L.; Tang Z.; Zheng Y. X.; Zuo J. L. Sci. Rep. 2015, 5, 14912.
[5]
(f) Brandt J.; Wang X.; Yang Y.; Campbell A.; Fuchter M. J. Am. Chem. Soc. 2016, 138, 9743.
[5]
(g) Han J.; Guo S.; Wang J.; Wei L.; Zhuang Y.; Liu S.; Zhao Q.; Zhang X.; Huang W. Adv. Opt. Mater. 2017, 5, 1700359.
[5]
(h) Yan Z.-P.; Luo X.-F.; Liao K.; Lin Z.-X.; Wu Z.-G.; Zhou Y.-H.; Zheng Y.-X. Dalton Trans. 2018, 47, 4045.
[5]
(i) Chen Y.; Li X.; Li N.; Quan Y.; Cheng Y.; Tang Y. Mater. Chem. Front. 2019, 3, 867.
[5]
(j) Fu G.; He Y.; Li W.; Wang B.; Lü X.; He H.; Wong W.-Y. J. Mater. Chem. C 2019, 7, 13743.
[5]
(k) Lu J.-J.; Tu Z.-L.; Luo X.-F.; Zhang Y.-P.; Qu Z.-Z.; Liang X.; Wu Z.-G.; Zheng Y.-X. J. Mater. Chem. C 2021, 9, 5244.
[5]
(l) Lu G.; Wu Z.-G.; Wu R.; Cao X.; Zhou L.; Zheng Y.-X.; Yang C.-L. Adv. Funct. Mater. 2021, 2102898.
[6]
(a) Imagawa T.; Hirata S.; Totani K.; Watanabe T.; Vacha M. Chem. Commun. 2015, 51, 13268.
[6]
(b) Feuillastre S.; Pauton M.; Gao L.; Desmarchelier A.; Riives A. J.; Prim D.; Tondelier D.; Ge?roy B.; Muller G.; Clavier G.; Pieters G. J. Am. Chem. Soc. 2016, 138, 3990.
[6]
(c) Li M.; Li S.-H.; Zhang D.; Cai M.; Duan L.; Fung M.-K.; Chen C.-F. Angew. Chem. Int. Ed. 2018, 57, 1.
[6]
(d) Song F.; Xu Z.; Zhang Q.; Zhao Z.; Zhang H.; Zhao W.; Qiu Z.; Qi C.; Zhang H.; Sung H. H. Y.; Williams I. D.; Lam J. W. Y.; Zhao Z.; Qin A.; Ma D.; Tang B. Z. Adv. Funct. Mater. 2018, 1800051.
[6]
(e) Zhang X.; Zhang Y.; Zhang H.; Quan Y.; Li Y.; Cheng Y.; Ye S. Org. Lett. 2019, 21, 439.
[6]
(f) Zhang Y.; Zhang X.; Zhang H.; Xiao Y.; Quan Y.; Ye S.; Cheng Y. J. Phys. Chem. C 2019, 123, 24746.
[6]
(g) Sun S.; Wang J.; Chen L.; Chen R.; Jin J.; Chen C.; Chen S.; Xie G.; Zheng C.; Huang W. J. Mater. Chem. C 2019, 7, 14511.
[6]
(h) Wang Y.; Zhang Y.; Hu W.; Quan Y.; Li Y.; Cheng Y. ACS Appl. Mater. Interfaces 2019, 11, 26165.
[6]
(i) Wu Z.-G.; Han H.-B.; Yan Z.-P.; Luo X.-F.; Wang Y.; Zheng Y.-X.; Zuo J.-L.; Pan Y. Adv. Mater. 2019, 1900524.
[6]
(j) Li M.; Wang Y.-F.; Zhang D.; Duan L.; Chen C. -F Angew. Chem. Int. Ed. 2020, 59, 3500.
[6]
(k) Yang S.-Y.; Wang Y.-K.; Peng C.-C.; Wu Z.-G.; Yuan S.; Yu Y.-J.; Li H.; Wang T.-T.; Li H.-C.; Zheng Y.-X.; Jiang Z.-Q.; Liao L.-S. J. Am. Chem. Soc. 2020, 142, 17756.
[6]
(l) Xu Y.; Wang Q.; Cai X.; Li C.; Wang Y. Adv. Mater. 2021, 2100652.
[6]
(m) Ni F.; Huang C.-W.; Tang Y.; Chen Z.; Wu Y.; Xia S.; Cao X.; Hsu J.-H.; Lee W.-K.; Zheng K.; Huang Z.; Wu C.-C.; Yang C. Mater. Horiz. 2021, 8, 547.
[6]
(n) Yan Z.-P.; Liu T.-T.; Wu R.; Liang X.; Li Z.-Q.; Zhou L.; Zheng Y.-X.; Zuo J.-L. Adv. Funct. Mater. 2021, 2103875.
[7]
(a) Uoyama H.; Goushi K.; Shizu K.; Nomura H.; Adachi C. Nature 2012, 492, 234.
[7]
(b) Tao Y.; Yuan K.; Chen T.; Xu P.; Li H.; Chen R.; Zheng C.; Zhang L.; Huang W. Adv. Mater. 2014, 26, 7931.
[7]
(c) Wong M. Y.; Zysman-Colman E. Adv. Mater. 2017, 29, 1605444.
[7]
(d) Im Y.; Kim M.; Cho Y. J.; Seo J.-A.; Yook K. S.; Lee J. Y. Chem. Mater. 2017, 29, 1946.
[7]
(e) Yang Z.; Mao Z.; Xie Z.; Zhang Y.; Liu S.; Zhao J.; Xu J.; Chi Z.; Aldred M. P. Chem. Soc. Rev. 2017, 46, 915.
[7]
(f) Cai X.; Su S.-J. Adv. Funct. Mater. 2018, 1802558.
[7]
(g) Zou Y.; Gong S.; Xie G.; Yang C. Adv. Optical Mater. 2018, 1800568.
[7]
(h) Liang X.; Tu Z.-L.; Zheng Y.-X. Chem. Eur. J. 2019, 25, 5623.
[7]
(i) Qiu Z.; Tan J.; Cai N.; Wang K.; Ji S.; Huo Y. Chin. J. Org. Chem. 2019, 39, 679. (in Chinese)
[7]
邱志鹏, 谭继华, 蔡宁, 王凯, 籍少敏, 霍延平, 有机化学, 2019, 39, 679).
[7]
(j) Wang T.; Hua X.; Yu Y.; Yuan Y.; Feng M.; Jiang Z. Chin. J. Org. Chem. 2019, 39, 1436. (in Chinese)
[7]
王彤彤, 华晓晨, 郁友军, 袁熠, 冯敏强, 蒋佐权, 有机化学, 2019, 39, 1436).
[7]
(k) Yu J.; Xiao Y.; Chen J. Chin. J. Org. Chem. 2019, 39, 3460. (in Chinese)
[7]
俞佳, 肖雅方, 陈嘉雄, 有机化学, 2019, 39, 3460).
[7]
(l) Cao H.; Li B.; Wan J.; Yu T.; Xie L.; Sun C.; Liu Y.; Wang J.; Huang W. Acta Chim. Sinica 2020, 78, 680. (in Chinese)
[7]
曹洪涛, 李波, 万俊, 余涛, 解令海, 孙辰, 刘玉玉, 王锦, 黄维, 化学学报, 2020, 78, 680).
[7]
(m) Zhou T.; Qian Y.; Wang H.; Feng Q.; Xie L.; Huang W. Acta Chim. Sinica 2021, 79, 557. (in Chinese)
[7]
周涛, 钱越, 王宏健, 冯全友, 解令海, 黄维, 化学学报, 2021, 79, 557).
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