手性有机光电功能材料及其圆偏振光发射与探测

doi:10.6023/A22030123

化学学报 ›› 2022, Vol. 80 ›› Issue (7): 970-992.DOI: 10.6023/A22030123 上一篇下一篇

综述

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)

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摘要/Abstract

手性有机半导体由于其新颖的性质引起了有机光电领域极大的研究兴趣. 将手性引入有机半导体材料不仅可以调控聚集态结构影响载流子输运进而影响光电器件的性能, 而且催生了圆偏振光直接发射与探测材料与器件的产生与发展. 手性材料与圆偏振光之间的相互作用使得其在3D显示、量子通讯、信息存储与处理等领域展示出广泛的应用前景. 本综述总结近年来手性有机光电材料及器件的研究进展, 主要围绕手性对有机半导体材料性质与器件性能的影响展开, 聚焦于手性有机半导体的圆偏振光直接发射与探测等研究, 旨在进一步为手性有机光电子领域的发展提供系统的认识.

关键词: 手性光电子, 手性有机半导体, 圆偏振光发射, 圆偏振光探测

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

引用此文

刘丽萱, 杨扬, 魏志祥. 手性有机光电功能材料及其圆偏振光发射与探测[J]. 化学学报, 2022, 80(7): 970-992.

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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图/表 25

图1. 手性有机光电材料与器件研究的主要内容[9]

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

图2. (a)手性小分子1的化学结构; (b)基于(R,R)-1,(S,S)-1,(R,S)-1薄膜场效应晶体管的输出曲线; (c)单一立体异构体(R,R)-1,(S,S)-1,(R,S)-1及其混合物的单晶结构; (d)手性小分子2的化学结构; (e)内消旋分子(R,S)-2, 单一手性分子(S,S)-2和外消旋体n[(S,S)-2]∶n[(R,R)-2]=1∶1单晶结构的堆积排列[9b,16]

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]

图3. 手性小分子3和4的化学结构[11a,18]

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

图4. 手性小分子5和6的化学结构[20-21]

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

图5. 手性小分子给体7和手性聚合物给体8的化学结构[22-23]

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

图6. 手性富勒烯衍生物受体9, 10, 手性聚合物给体11, 手性非富勒烯小分子受体12的化学结构[24⇓-26]

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

图7. 电致圆偏振光直接发射器件工作原理[27]

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

图8. 手性聚合物13, 非手性聚合物14、15和手性溶剂16化学结构[30⇓-32]

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

图9. 手性小分子17~22的化学结构[34⇓⇓⇓⇓-39]

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

图10. 电致圆偏振发光材料分类: (a)手性共轭聚合物; (b)手性小分子掺杂的非手性共轭聚合物; (c)手性过渡金属配合物; (d)手性发光小分子[27,42]

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]

图11. 带手性侧链的聚合物23~26, 手性AIE聚合物27和手性TADF聚合物28[15,43⇓⇓-46]

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

图12. (a)基于手性螺烯小分子30掺杂的非手性聚合物29的电致圆偏振发光器件; (b~d)厚度依赖的(b) gabs, (c) gPL, (d) gEL; (e)含空穴阻挡层31的OLED器件结构; (f)空穴阻挡层31的化学结构; (g)随层31厚度变化发射区域移动的示意图[47⇓-49]

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]

图13. 手性过渡金属配合物32~34的化学结构[27,42a,50]

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

图14. 手性荧光小分子35, 36和手性TADF小分子37~39[51⇓⇓⇓-55]

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

表1. 光电探测器的基本参数

Table 1. Photodetector metrics of performance

图15. (a)基于手性小分子螺烯40有机场效应晶体管实现直接圆偏振光探测 (b, c)基于P-40(b)/M-40(c)的有机场效应晶体管在左右旋圆偏光下的响应[58]; (d)基于单一手性的富勒烯衍生物41构筑的有机场效应晶体管实现圆偏振光直接探测; (e)有机场效应晶体管在左右旋圆偏光下的开关响应[59]

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]

图16. (a)基于手性小分子42有机场效应晶体管实现圆偏振光探测; (b)手性小分子42溶液、薄膜、纳米线的gabs; (c)基于手性小分子42纳米线及薄膜的有机场效应晶体管在左右旋圆偏光下的响应; (d)基于手性小分子43的单晶有机场效应晶体管实现圆偏振光探测[60-61]

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]

图17. (a)手性PDI双-[7]杂螺烯P-44和M-44的分子结构; (b)不同厚度P-44和M-44薄膜在740 nm(圆圈)和635 nm(三角形)的gabs; (c)基于P-44和M-44的薄膜有机场效应晶体管在730 nm左右旋圆偏光下的开关响应及相应的响应度的不对称因子[62]

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]

图18. (a)左右旋圆偏光诱导分子相反的手性M-/P-45; (b)未经处理的薄膜及左右旋圆偏振光辐射诱导后的薄膜的CD光谱; (c)基于M-/P-45有机场效应晶体管在左右旋圆偏光下的响应; (d)左右旋圆偏光诱导的有机场效应晶体管的gph[63]

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]

图19. 基于近红外吸光的窄带系π-共轭聚合物46和近红外反射胆甾相液晶网络薄膜的直接圆偏振光探测器[64]

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]

图20. (a)基于手性聚芴衍生物47有机太阳能电池的直接圆偏振光探测器; (b)手性聚芴衍生物47薄膜的gabs与厚度的关系; (c)双层有机太阳能电池的光学模型, 入射的l-CPL经Al电极反射后反转为r-CPL; (d)不同厚度下器件的gsc[65]

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]

图21. (a)基于手性方酸衍生物48有机太阳能电池的直接圆偏振光探测器; (b)不同厚度薄膜在545 nm处吸收校准的gabs; (c)不同厚度下器件的gsc[66]

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]

图22. (a)非手性聚噻吩衍生物P3CT 49和手性小分子1,1'-联萘BN 50的化学结构; (b) 49/R-50和49/S-50的CD吸收光谱; (c) 49/R-50和49/S-50异质结器件在左右旋圆偏光辐照下的最大光电流的变化; (d)手性聚噻吩纳米线在左右旋圆偏光下的光电流; (e) CPL探测的装置示意图; (f)手性产生的轨道角动量作用下的电子激发与复合的示意图[67-68]

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]

图23. 手性螺烯P-/M-40掺杂的F8T2 51为电子给体, 非手性C60为受体的双层平面异质结有机光电二极管器件[69]

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]

图24. (a)基于手性DPP6T衍生物:PC61BM OSCs的直接圆偏振光探测; (b) S-/R-52纯膜及其与PC61BM共混膜厚度归一化的CD光谱; (c) S-/R-52:PC61BM共混膜吸收校准的gabs; (d)基于S-/R-52:PC61BM OSCs在不同波长下的gsc与活性层的超分子手性耦合; (e)不同活性层厚度的S-/R-52:PC61BM OSCs在606 nm的gsc . 黑点和黑线代表模拟计算得到的数据及其拟合曲线[70]

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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