| 254 | 0 | 67 |
| 下载次数 | 被引频次 | 阅读次数 |
圆偏振有机发光二极管(circularly polarized organic light-emitting diodes,CP-OLEDs)因其可直接产生圆偏振电致发光的本征特性，在三维显示、光学信息加密等领域展现出重大应用价值。然而，如何兼顾高器件效率和高不对称因子(gEL)是目前的领域挑战和研究热点。近年来，随着手性超分子组装策略的快速发展，研究者们发现该体系可通过精准调控π-π堆积、氢键等分子间相互作用，构建长程有序的螺旋纳米结构，实现较高的gEL，且保持较好的器件效率。因此，手性超分子组装体系成为实现兼具高器件效率和高gELCP-OLEDs的最有效策略之一。此外，手性自组装或共组装过程通常伴随着手性传递、手性诱导和分子间Förster共振能量转移，这有利于诱导非手性染料实现圆偏振电致发光，有效降低手性发光材料的合成难度。本文从手性超分子自组装和手性超分子共组装2个方面，分析了分子间作用力对手性超分子组装过程的影响，探讨了高阶有序的螺旋结构对手性传递、诱导和放大机制的作用，并总结了其在CP-OLEDs中的最新研究进展：通过精准调控π-π堆积、氢键等分子间相互作用，手性分子可自组装形成螺旋纳米结构，或与非手性发光体共组装实现手性诱导。实验结果表明，手性液晶材料的层状序构和能量转移协同作用可显著提升器件效率，且可通过外场动态调控螺旋周期与偏振方向。本综述为未来开发兼具高gEL值与高效率的CP-OLEDs提供了理论指导。
Abstract：Circularly polarized organic light-emitting diodes(CP-OLEDs) have demonstrated significant application potential in areas such as 3D displays and optical information encryption, owing to their intrinsic capability to directly generate circularly polarized electroluminescence. However, achieving both high device efficiency and a high electroluminescent dissymmetry factor(gEL) remains a major challenge and a focal research topic in this field. Recent advances in chiral supramolecular assembly demonstrate that this system can construct long-range ordered helical nanostructures by precisely regulating intermolecular interactions, such as π-π stacking and hydrogen bonding. This approach facilitates the attainment of a high gELvalue while maintaining favorable device efficiency. Consequently, chiral supramolecular assembly systems have emerged as one of the most effective strategies for realizing CP-OLEDs featuring both high device efficiency and elevated gELvalues. Furthermore, the processes of chiral self-assembly or co-assembly frequently involve chiral transfer, chiral induction, and intermolecular Förster resonance energy transfer. These processes are advantageous for inducing achiral dyes to achieve circularly polarized electroluminescence, thereby effectively reducing the synthetic complexity of chiral luminescent materials. This paper analyzes the influence of intermolecular forces on the chiral supramolecular assembly process from two perspectives: Chiral supramolecular self-assembly and chiral supramolecular co-assembly. It investigates the role of highly ordered helical structures in the mechanisms of chirality transfer, chirality induction, and chirality amplification. Additionally, it summarizes the most recent research advancements in CP-OLEDs: Through precise regulation of intermolecular interactions such as π-π stacking and hydrogen bonding, chiral molecules can self-assemble into helical nanostructures or co-assemble with achiral luminophores to achieve chirality induction. Experiments demonstrate that the synergistic effect of lamellar ordering and energy transfer in chiral liquid crystal materials can significantly enhance device efficiency, allowing external fields to dynamically tune the helical pitch and polarization direction. This review provides theoretical guidance for the future development of CP-OLEDs with both high gELvalues and high efficiency.
[1] HUCK N P M, JAGER W F, de LANGE B, et al. Dynamic control and amplification of molecular chirality by circular polarized light[J]. Science, 1996, 273(5282):1686-1688.
[2] ZHANG Y F, SCHUSTER G B. Photoresolution of an axially chiral bicyclo[3.2.1] octan-3-one:phototriggers for a liquid crystal-based optical switch[J]. The Journal of Organic Chemistry, 1995, 60(22):7192-7197.
[3] FARSHCHI R, RAMSTEINER M, HERFORT J, et al.Optical communication of spin information between light emitting diodes[J]. Applied Physics Letters, 2011, 98(16):162508.
[4] YE Z Y, WU H, XU Y L, et al. Deep-blue narrowband hetero[6]helicenes showing circularly polarized thermally activated delayed fluorescence toward high-performance OLEDs[J]. Advanced Materials, 2024, 36(1):2308314.
[5] GONG M H, YUAN L, ZHENG Y X, et al. Planar chiral thermally activated delayed fluorescence materials based on di[2.2]paracyclophane for circularly polarized electroluminescence[J]. Advanced Functional Materials, 2024, 34(47):2314205.
[6] WANG X Z, XING S, XIAO X, et al. Axial chiral biphenyl MR-TADF enantiomers for efficient narrowband circularly polarized electroluminescence[J]. Advanced Functional Materials, 2025, 35(1):2412044.
[7] GUO W C, ZHAO W L, TAN K K, et al. B, N-embedded hetero[9] helicene toward highly efficient circularly polarized electroluminescence[J]. Angewandte Chemie International Edition, 2024, 63(18):e202401835.
[8] MENG G Y, ZHOU J P, HAN X S, et al. B-N covalent bond embedded double Hetero-[n]helicenes for pure red narrowband circularly polarized electroluminescence with high efficiency and stability[J]. Advanced Materials, 2024,36(5):2307420.
[9] SANG Y T, HAN J L, ZHAO T H, et al. Circularly polarized luminescence in nanoassemblies:generation, amplification, and application[J]. Advanced Materials, 2020, 32(41):1900110.
[10] HUANG T T, YUAN L, LU X Y, et al. Efficient circularly polarized multiple resonance thermally activated delayed fluorescence from B, N-embedded hetero[8] helicene enantiomers[J]. Chemical Science, 2024, 15(37):15170-15177.
[11] ZHAO P, GUO W C, LI M, et al. Single-molecule white circularly polarized photoluminescence and electroluminescence from dual-emission enantiomers[J]. Angewandte Chemie International Edition, 2024, 63(36):e202409020.
[12] RICHARDSON F S, RIEHL J P. Circularly polarized luminescence spectroscopy[J]. Chemical Reviews, 1977, 77(6):773-792.
[13] SÁNCHEZ-CARNERERO E M, AGARRABEITIA A R,MORENO F, et al. Circularly polarized luminescence from simple organic molecules[J]. Chemistry-A European Journal, 2015, 21(39):13488-13500.
[14] ONIKI J, MORIUCHI T, KAMOCHI K, et al. Linear[3]spirobifluorenylene:an S-shaped molecular geometry of poligophenyls[J]. Journal of the American Chemical Society,2019, 141(45):18238-18245.
[15] LUO X F, HAN H B, YAN Z P, et al. Multicolor circularly polarized photoluminescence and electroluminescence with 1,2-diaminecyclohexane enantiomers[J]. ACS Applied Materials&Interfaces, 2020, 12(20):23172-23180.
[16] WANG Y, ZHAO W L, GAO Z W, et al. Switchable topologically chiral[2]catenane as multiple resonance thermally activated delayed fluorescence emitter for efficient circularly polarized electroluminescence[J]. Angewandte Chemie, 2025, 64(5):e202417458.
[17] ZHAO J J, ZENG K, DOU W T, et al. Boosted circularly polarized luminescence of a chiral metallacage through coassembly in confined microfluidic environments[J]. Advanced Functional Materials, 2025, 35(3):2413920.
[18] DING X Y, SHI L X, WANG J Y, et al. Doping copper(I)in Ag7cluster for circularly polarized OLEDs with external quantum efficiency of 26.7%[J]. Angewandte Chemie International Edition, 2025, 64(5):e202417934.
[19] DAVYDOVA M P, XU T, AGAFONTSEV A M, et al. Toward rhenium-based circularly polarized OLEDs using tailored chiral Re(CO)3emitters[J]. Angewandte Chemie International Edition, 2025, 64(7):e202419788.
[20] YAN H W, HE Y L, WANG D, et al. Aggregation-induced emission polymer systems with circularly polarized luminescence[J]. Aggregate, 2023, 4(4):e331.
[21] WANG Y F, LI M, TENG J M, et al. Chiral TADF-active polymers for high-efficiency circularly polarized organic light-emitting diodes[J]. Angewandte Chemie International Edition, 2021, 60(44):23619-23624.
[22] LEE D M, SONG J W, LEE Y J, et al. Control of circularly polarized electroluminescence in induced twist structure of conjugate polymer[J]. Advanced Materials, 2017,29(29):1700907.
[23] ZHANG Y X, YU W T, LI H, et al. Induced CPL-active materials based on chiral supramolecular co-assemblies[J].Chemistry-A European Journal, 2023, 29(22):e202204039.
[24] YUAN Y X, JIA J H, SONG Y P, et al. Fluorescent TPE macrocycle relayed light-harvesting system for bright customized-color circularly polarized luminescence[J]. Journal of the American Chemical Society, 2022, 144(12):5389-5399.
[25] SONG I, AHN J, AHN H, et al. Helical polymers for dissymmetric circularly polarized light imaging[J]. Nature,2023, 617(7959):92-99.
[26] WU Y, LI M Q, ZHENG Z G, et al. Liquid crystal assembly for ultra-dissymmetric circularly polarized luminescence and beyond[J]. Journal of the American Chemical Society, 2023, 145(24):12951-12966.
[27] ZHONG H, GAO X B, ZHAO B, et al.″Matching rule″for generation, modulation and amplification of circularly polarized luminescence[J]. Accounts of Chemical Research,2024, 57(8):1188-1201.
[28] GUO C H, ZHANG Y W, ZHAO W L, et al. Chiral coassembly with narrowband multi-resonance characteristics for high-performance circularly polarized organic lightemitting diodes[J]. Advanced Materials, 2024, 36(38):2406550.
[29] ZHANG Y, LI D, LI Q H, et al. High comprehensive circularly polarized electroluminescence performance improved by chiral coassembled host materials[J]. Advanced Functional Materials, 2023, 33(44):2309133.
[30] TAN K K, GUO W C, ZHAO W L, et al. Self-assembled chiral polymers exhibiting amplified circularly polarized electroluminescence[J]. Angewandte Chemie International Edition, 2024:e202412283.
[31] AKAGI K, PIAO G, KANEKO S, et al. Helical polya-cetylene synthesized with a chiral nematic reaction field[J].Science, 1998, 282(5394):1683-1686.
[32] ZHANG Y X, LI H, GENG Z X, et al. Inverted circularly polarized luminescence behavior induced by helical nanofibers through chiral co-assem bly from achiral liquid crystal polymers and chiral inducers[J]. ACS Nano, 2022,16(2):3173-3181.
[33] ZHANG X, XU Y Y, VALENZUELA C, et al. Liquid crystal-templated chiral nanomaterials:from chiral plasmonics to circularly polarized luminescence[J]. Light:Science and Applications, 2022, 11:223.
[34] ZHOU M D, LU P, XU Z P, et al. Circularly polarized luminescent liquid crystal copolymers constructed by tripletsinglet Förster-resonance energy transfer:achieving large glumvalues, long lifetime, and high photoluminescence quantum yield[J]. Advanced Optical Materials, 2024, 12(28):2401208.
[35] CHEN Y H, ZHANG Y X, LI H, et al. Dynamic circularly polarized luminescence with tunable handedness and intensity enabled by achiral dichroic dyes in cholesteric liquid crystal medium[J]. Advanced Materials, 2022, 34(28):2202309.
[36] ZOU G, JIANG Z H, LI D, et al. Efficient helical columnar emitters of chiral homoleptic Pt （Ⅱ） metallomesogens for circularly polarized electroluminescence[J]. Chemical Science, 2024, 15(44):18534-18542.
[37] HAN D X, YANG X F, HAN J L, et al. Sequentially amplified circularly polarized ultraviolet luminescence for enantioselective photopolymerization[J]. Nature Communications, 2020, 11(1):5659.
[38] ZHANG H Y, CHANG X Y, MA C Y, et al. Two cholesterol-containing pyrene derivatives:subtle spacer difference, diverse stimuli-responsive luminescence, chirality,and self-assembly behaviors[J]. ACS Applied Materials&Interfaces, 2022, 14(38):43926-43936.
[39] WANG Y F, LIAO Y W, CABRY C P, et al. Highly efficient blueish-green fluorescent OLEDs based on AIE liquid crystal molecules:from ingenious molecular design to multifunction materials[J]. Journal of Materials Chemistry C, 2017, 5(16):3999-4008.
[40] DE J, ABDUL HASEEB M M, YADAV R A K, et al.AIE-active mechanoluminescent discotic liquid crystals for applications in OLEDs and bio-imaging[J]. Chemical Communications, 2020, 56(91):14279-14282.
[41] LI Q H, ZOU G, LI D, et al. Strong circularly polarized phosphorescence of achiral Pt(II)metallomesogen induced by using a chiral co-assembly strategy[J]. Advanced Optical Materials, 2024, 12(16):2303185.
[42] WANG Y F, FAN J, SHI J W, et al. Influence of integrated alkyl-chain length on the mesogenic and photophysical properties of platinum-based metallomesogens and their application for polarized white OLEDs[J]. Dyes and Pigments, 2016, 133:238-247.
[43] TAUCHI D, KOIDA T, NOJIMA Y, et al. Aggregationinduced circularly polarized phosphorescence of Pt(II)complexes with an axially chiral BINOL ligand[J]. Chemical Communications, 2023, 59(27):4004-4007.
[44] QIAN G W, YANG X F, WANG X B, et al. Chiral platinum-based metallomesogens with highly efficient circularly polarized electroluminescence in solution-processed organic light-emitting diodes[J]. Advanced Optical Materials,2020, 8(20):2000775.
[45] FAN P, FANG Z, WANG S Y, et al. High-efficiency circularly polarized emission from liquid-crystalline platinum complexes[J]. Chinese Chemical Letters, 2023, 34(6):107934.
[46] LAI X Y, ZHONG Q H, XIAO C, et al. Liquid-crystalline circularly polarised fluorescent emitters with a high luminescence dissymmetry factor[J]. Chemical Communications, 2024, 60(15):2026-2029.
[47] HE B H, ZHONG Q H, DONG Q W, et al. Liquid-crystalline circularly polarised TADF emitters for high-efficiency, solution-processable organic light-emitting diodes[J]. Materials Horizons, 2024, 11(5):1251-1260.
[48] XIA Y R, DUAN H D, HAO A Y, et al. Photoresponsive supramolecular chiral composites based on hydrogenbonded coassembly[J]. The Journal of Physical Chemistry C, 2021, 125(51):28108-28114.
[49] ZHENG S Y, HAN J L, JIN X, et al. Halogen bonded chiral emitters:generation of chiral fractal architecture with amplified circularly polarized luminescence[J]. Angewandte Chemie International Edition, 2021, 60(42):22711-22716.
[50] ALBANO G, PESCITELLI G, di BARI L. Chiroptical properties in thin films ofπ-conjugated systems[J]. Chemical Reviews, 2020, 120(18):10145-10243.
[51] WAN L, WADE J, SALERNO F, et al. Inverting the handedness of circularly polarized luminescence from light-emitting polymers using film thickness[J]. ACS Nano,2019, 13(7):8099-8105.
[52] YANG Y, da COSTA R C, SMILGIES D M, et al. Induction of circularly polarized electroluminescence from an achiral light-emitting polymer via a chiral small-molecule dopant[J]. Advanced Materials, 2013, 25(18):2624-2628.
[53] WAN L, WADE J, SHI X Y, et al. Highly efficient inverted circularly polarized organic light-emitting diodes[J].ACS Applied Materials&Interfaces, 2020, 12(35):39471-39478.
[54] WAN L, WADE J, WANG X H, et al. Engineering the sign of circularly polarized emission in achiral polymerchiral small molecule blends as a function of blend ratio[J].Journal of Materials Chemistry C, 2022, 10(13):5168-5172.
[55] WARD M D, WADE J, SHI X Y, et al. Highly selective high-speed circularly polarized photodiodes based onπ-conjugated polymers[J]. Advanced Optical Materials, 2022,10(2):2101044.
[56] WAN L, SHI X Y, WADE J, et al. Strongly circularly polarized crystalline and β-phase emission from poly(9,9-dioctylfluorene)-based deep-blue light-emitting diodes[J]. Advanced Optical Materials, 2021, 9(19):2100066.
[57] YAN H, WADE J, WAN L, et al. Enhancing hole carrier injection via low electrochemical doping on circularly polarized polymer light-emitting diodes[J]. Journal of Materials Chemistry C, 2022, 10(25):9512-9520.
[58] ZHANG X Y, XU Z R, ZHANG Y, et al. High brightness circularly polarized electroluminescence from conjugated polymer F8BT induced by chiral binaphthyl-pyrene[J].Journal of Materials Chemistry C, 2020, 8(44):15669-15676.
[59] ZHANG X Y, XU Z R, ZHANG Y, et al. Controllable circularly polarized electroluminescence performance improved by the dihedral angle of chiral-bridged binaphthyltype dopant inducers[J]. ACS Applied Materials&Interfaces, 2021, 13(46):55420-55427.
[60] GENG Z X, ZHANG Y X, ZHANG Y, et al. Circularly polarized electroluminescence from an achiral fluorophore induced by co-assembly with chiral polymers[J]. Journal of Materials Chemistry C, 2021, 9(36):12141-12147.
[61] GENG Z X, ZHANG Y X, ZHANG Y, et al. Amplified circularly polarized electroluminescence behavior triggered by helical nanofibers from chiral co-assembly polymers[J].Angewandte Chemie International Edition, 2022, 61(23):e202202718.
[62] GENG Z X, LIU Z, LI H, et al. Inverted and amplified CP-EL behavior promoted by AIE-active chiral co-assembled helical nanofibers[J]. Advanced Materials, 2023, 35(8):2209495.
[63] LI H, LI D, FU C Y, et al. Strong circularly polarized electroluminescence promoted by using chiral co-assembled liquid crystal polymers[J]. Advanced Optical Materials, 2025, 13(5):2402426.
[64] LI D, JIANG Z H, ZHENG S W, et al. Tunable circularly polarized electroluminescence behaviors from chiral co-assembled conjugated liquid crystal polymers[J]. Journal of Colloid and Interface Science, 2025, 678:1213-1222.
[65] ZHANG Y, LI Y P, QUAN Y W, et al. Remarkable white circularly polarized electroluminescence based on chiral co-assembled helix nanofiber emitters[J]. Angewandte Chemie International Edition, 2023, 62(1):e202214424.
[66] MORENO-NARANJO J M, FURLAN F, WANG J X, et al. Enhancing circularly polarized electroluminescence through energy transfer within a chiral polymer host[J].Advanced Materials, 2024, 36(33):2402194.
基本信息:
DOI：10.12194/j.ntu.20250220001
中图分类号:TN383.1;O641.3
引用信息:
[1]楚欣鹏,张雨霞,马云.基于手性超分子组装策略的圆偏振有机发光二极管[J].南通大学学报(自然科学版),2026,25(02):1-13.DOI:10.12194/j.ntu.20250220001.
基金信息:
国家重点研发计划项目(2022YFA1204404); 国家自然科学基金青年科学基金项目(62305172); 江苏省高校自然科学基金项目(23KJB430026); 南京邮电大学引进人才科研启动基金项目(NY223052)
2025-06-18
2025-06-18
2025-06-18