Chiral Organic Optoelectronic Materials and Circularly Polarized Light Luminescence and Detection

doi:10.6023/A22030123

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (7): 970-992.DOI: 10.6023/A22030123 Previous Articles Next Articles

Review

手性有机光电功能材料及其圆偏振光发射与探测

刘丽萱^a^,^b, 杨扬^a, 魏志祥^a^,^b^,^*()

a 国家纳米科学中心中国科学院纳米科学卓越中心中国科学院纳米系统与多级次制造重点实验室北京 100190
b 中国科学院大学未来技术学院北京 100049

投稿日期:2022-03-21 发布日期:2022-05-31
通讯作者: 魏志祥

作者简介:

刘丽萱, 中国科学院国家纳米科学中心在读博士生. 2017年9月进入国家纳米中心物理化学专业攻读博士研究生, 师从魏志祥研究员. 主要从事手性有机半导体材料的合成及器件制备等研究.

杨扬, 博士, 中国科学院国家纳米科学中心特别研究助理. 2018年在国家纳米中心获得理学博士学位, 导师魏志祥研究员. 主要从事超分子手性有机导电和半导体材料自组装以及相应光电功能器件的制备及性能研究.

魏志祥, 中国科学院国家纳米科学中心研究员、博士生导师. 主要从事有机光电材料的自组装与柔性器件. 通过研究自组装过程中非共价相互作用的作用机制, 调节多种弱相互作用协同组装的过程, 制备结构和性能可控的有机光电功能纳米材料, 阐明从分子结构到微纳米结构, 再到宏观结构中结构和性能的传递规律; 开展自组装微纳米结构在太阳能电池、储能器件和传感器件等柔性电子器件中的应用基础研究.

基金资助:
中国科学技术部(2021YFA1200303); 国家自然科学基金(21721002); 国家自然科学基金(52003065); 国家自然科学基金(51673049); 国家自然科学基金(21975059); 中国科学院(XDB36010200); 中国博士后科学基金(2019M660584)

Chiral Organic Optoelectronic Materials and Circularly Polarized Light Luminescence and Detection

Lixuan Liu^a^,^b, Yang Yang^a, Zhixiang Wei^a^,^b()

a CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing 100190, China
b School of Future Technology, University of Chinese Academy of Sciences, Beijing 100049, China

Received:2022-03-21 Published:2022-05-31
Contact: Zhixiang Wei
Supported by:
Ministry of Science and Technology of China(2021YFA1200303); National Natural Science Foundation of China(21721002); National Natural Science Foundation of China(52003065); National Natural Science Foundation of China(51673049); National Natural Science Foundation of China(21975059); Strategic Priority Research Program of Chinese Academy of Sciences(XDB36010200); China Postdoctoral Science Foundation(2019M660584)

Chiral organic semiconductors have stimulated extensive research interests in the field of organic optoelectronics due to their fascinating properties. The incorporation of chirality into organic semiconducting materials can not only control their aggregation states by virtue of the unique non-covalent interactions among chiral molecules to regulate electronic/ optoelectronic properties, but also facilitates the emergence and development of circularly polarized light direct luminescence and detection. The interactions between chiral materials and circularly polarized light allow them to show broad application prospects in the field of three-dimensional display, quantum communications, information storage and processing, and so forth. This review summarizes the research progress of chiral organic optoelectronic materials and devices in recent years. It mainly reviews the influence of chirality on material properties and device performance, focusing on the applications of circularly polarized light luminescence and detection using chiral organic semiconductors, and aiming to promote the development of relevant research in the field of chiral optoelectronics.

Key words: chiral optoelectronics, chiral organic semiconductor, circularly polarized light luminescence, circularly polarized light detection

Cite this article

Lixuan Liu, Yang Yang, Zhixiang Wei. Chiral Organic Optoelectronic Materials and Circularly Polarized Light Luminescence and Detection[J]. Acta Chimica Sinica, 2022, 80(7): 970-992.

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Fig. & Tab. 25

Figure 1. The main research content of chiral organic optoelectronic materials and devices[9]

Figure 2. (a) Chemical structure of chiral small molecule 1; (b) typical output characteristics of thin-film OFETs of (R,R)-1, (S,S)-1, (R,S)-1; (c) single-crystal structures of isolated stereoisomers (R,R)-1, (S,S)-1, (R,S)-1 and as-synthesized 1; (d) chemical structure of chiral small molecule 2; (e) single-crystal structures of mesomer (R,S)-2, pure enantiomer (S,S)-2, and racemate n[(S,S)-2]∶n[(R,R)-2]=1∶1[9b,16]

Figure 3. Chemical structures of chiral small molecule 3 and 4[11a,18]

Figure 4. Chemical structures of chiral small molecule 5 and 6[20-21]

Figure 5. Chemical structures of chiral small-molecule donor 7 and chiral polymer donor 8[22-23]

Figure 6. Chemical structures of chiral fullerene derivative acceptor 9, 10, chiral polymer donor 11, and chiral non-fullerene acceptor 12[24⇓-26]

Figure 7. The schematic diagram of device architecture of circular polarized electroluminescence[27]

Figure 8. Chemical structures of chiral polymer 13, achiral polymer 14, 15, and chiral solvent 16[30⇓-32]

Figure 9. Chemical structures of chiral small molecule 17~22 [34⇓⇓⇓⇓-39]

Figure 10. Classification of the circular polarized electroluminescence materials: (a) polymers with chiral side chains; (b) achiral polymers with chiral dopants; (c) chiral transition metal complexes; (d) chiral emissive small molecules[27,42]

Figure 11. Chemical structures of polymer with chiral side chain 23~26, chiral AIE polymer 27, and chiral TADF polymer 28[15,43⇓⇓-46]

Figure 12. (a) Direct CPEL device based on achiral polymer 29 doped with chiral helicene 30; (b~d) the dependence of (b) gabs, (c) gPL, (d) gEL on active layer thickness; (e) device configuration of the OLED consisting a hole-blocking layer 31; (f) the chemical structure of hole-blocking layer 31; (g) schematic diagram of the moving the emission zone with the layer thickness of 31[47⇓-49]

Figure 13. Chemical structures of chiral-metal complex 32~34[27,42a,50]

Figure 14. Chemical structures of chiral fluorescent small molecule 35, 36, and chiral TADF small molecule 37~39[51⇓⇓⇓-55]

参数	单位	公式	备注
响应度R	A•W^-1	R=J_ph/L_light	J_ph: 光电流 L_light: 光强
外量子效率EQE	%	EQE=J_phhc/(L_ineλ)×100	h: 普朗克常量 c: 光速, e: 元电荷 λ: 波长
噪声等效功率NEP	W•Hz^-1/2	NEP=(I_N/B^1/2)/R	I_N: 噪音电流 B: 带宽
比探测率D*	Jones	D=A^1/2/NEP* =R(AB)^1/2/I_N	A: 器件面积
线性动态范围LDR	dB	LDR=20log(L_max/L_min)	L_max, L_min: 最大, 最小光强

Table 1. Photodetector metrics of performance

Figure 15. (a) The direct CPL detection based on OFETs containing chiral helicene 40; (b, c) response of P-40 (b)/M-40 (c) OFETs to l-and r-CPL[58]; (d) the OFET containing single-handed fullerene derivate 41 for direct CPL detection; (e) the switching characteristics of OFETs under the illumination of l- and r-CPL[59]

Figure 16. (a) The direct CPL detection based on chiral small molecule 42; (b) the gabs of solutions, films and nanowires of S-/R-42; (c) response of S-/R-42 nanowires- and films-based OFETs to l-and r-CPL; (d) the direct CPL detection based on chiral small molecule 43[60-61]

Figure 17. (a) The molecular structures of P-44 and M-44; (b) the gabs of P-44 and M-44 thin films with varied thickness. Circles and triangles mean gabs values at 740 and 635 nm, respectively; (c) the switching characteristics of P-/M-44-based OFETs under CPL irradiations (λ=730 nm) and the corresponding dissymmetry factor of responsivity[62]

Figure 18. (a) Opposite chirality of M-/P-45 induced by l-/r-CPL; (b) CD spectra of pristine films, and pristine films irradiated with l- and r-CPL, respectively; (c) photoresponse of M-/P-45 based OFETs to l- and r-CPL; (d) the gph of l-/r-CPL induced OFETs[63]

Figure 19. The direct CPL detection based on thin-film OFETs including an NIR-absorbing small-bandgap π-conjugated polymer (PODTPPD-BT) 46 and NIR-reflecting cholesteric liquid crystal network films[64]

Figure 20. (a) The direct CPL detection based on chiral polymer 47 OSCs; (b) the dependence of gabs on the film thickness of chiral polymer 47; (c) optical model for this bilayer OSC. The incoming l-CPL changes to r-CPL upon reflection at the aluminum electrode; (d) the dependence of gsc on film thickness[65]

Figure 21. (a) The direct CPL detection based on chiral squaraine 48 OSCs; (b) reflection-calibrated gabs with varying active layer thicknesses at 545 nm; (c) the gsc with varying active layer thicknesses[66]

Figure 22. (a) The chemical structures of achiral polymer 49 and chiral small molecule 50; (b) CD spectra of 49/R-50 and 49/S-50 hybrid films; (c) variation of maximum photocurrent of 49/R-50 and 49/S-50 hybrid devices illuminated with alternating l-/r-CPL; (d) photocurrent of chiral polythiophene nanowires illuminated with alternating l-/r-CPL; (e) the setup of CPL detection; (f) diagram of electron excitation and recombination under the effect of chirality generated orbital angular momentum[67-68]

Figure 23. The direct CPL detection based on bilayer photodiode, in which achiral polymer 51 dopped with chiral helicene P-/M-40 is used as electron donor and achiral C60 is used as electron acceptor[69]

Figure 24. (a) The direct CPL detection based on chiral DPP6T:PC61BM OSCs; (b) thickness-normalized CD spectra of S-/R-52 neat and their blended films with PC61BM; (c) reflection-calibrated gabs of S-/R-52:PC61BM blended films; (d) gsc of the S-/R-52:PC61BM OSCs coupled to the supramolecular chirality of the active layers; (e) thickness-dependent gsc under 606 nm l- and r-CPL illumination of S-/R-52:PC61BM OSCs. The black data points represent the simulated gsc, and the black line is the fitting trend based on the simulated gsc[70]

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手性有机光电功能材料及其圆偏振光发射与探测

Chiral Organic Optoelectronic Materials and Circularly Polarized Light Luminescence and Detection

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