Citation: Xiangyu Dong, Shaogang Shen, Yuanyuan Qin, Xiaoxiao Hu, Honglei Gao, Guanhao Liu, Teng Gao, Zhi Pang, Pengfei Wang, Ying Wang. Synthesis and properties of binaphthyl chiral thermally activated delayed fluorescence molecules using thioxanthone as acceptor[J]. Chinese Chemical Letters, ;2023, 34(12): 108311. doi: 10.1016/j.cclet.2023.108311 shu

Synthesis and properties of binaphthyl chiral thermally activated delayed fluorescence molecules using thioxanthone as acceptor

Xiangyu Dong ^{a, b} ,
Shaogang Shen ^{a, b} ,
Yuanyuan Qin ^{a, b} ,
Xiaoxiao Hu ^c ,
Honglei Gao ^{a, b} ,
Guanhao Liu ^{a, b} ,
Teng Gao ^{a, b} ,
Zhi Pang ^{a, b} ,
Pengfei Wang ^{a, b} ,
Ying Wang ^{a, b, *,}

a.
Key Laboratory of Photochemical Conversion and Optoelectronic Materials and CityU–CAS Joint Laboratory of Functional Materials and Devices, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
School of Chemistry and Chemical Engineering, Suzhou University, Suzhou 234000, China

wangy@mail.ipc.ac.cn

Received Date: 7 January 2023
Revised Date: 9 February 2023
Accepted Date: 6 March 2023
Available Online: 15 March 2023

Figures(6)

The currently reported axial chiral molecules based on the 3,3′-substitution of the binaphthyl skeleton are limited by intrinsic fluorescence properties, resulting in generally low device efficiencies (EQE < 5%) of related organic light emitting diodes (OLEDs). Herein, we designed and synthesized four pair of chiral binaphthyl enantiomers (R/S-1 − R/S-4) adopting acceptor-donor-donor-acceptor (ADDA) structure by introducing different thioxanthone modification groups on the 3,3′-position of 2,2′-dimethoxy-1,1′-binaphthalene. Among them, emitter R/S-2 and R/S-4 obtained by enhancing intramolecular charge transfer exhibited TADF characteristics due to relatively small ΔE_ST of 0.12 eV and 0.17 eV, and relatively moderate SOC matrix elements of 0.28 cm⁻¹ and 0.10 cm⁻¹ between the ¹CT and ³LE states. The CD spectra of these enantiomers in diluted solutions showed perfect mirror images and reasonable g_abs for small organic molecules (10⁻⁴–10⁻³). And the external quantum efficiencies (EQE) of 10.9% and 8.32% for device A and B based on emitter S-2 and S-4 were highest compared with currently reported axial chiral molecules based on the 3,3′-position substitution of binaphthyl skeleton, providing simple molecular design strategies to construct efficient CP-OLED device.
- Thermally activated delayed fluorescence,
- Organic light emitting diodes,
- Binaphthyl skeleton,
- Electronic circular dichroism,
- Circularly polarized luminescence,
- Thioxanthone
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