基于氰基化9-苯基芴衍生物的激基复合物发光与性质研究

doi:10.6023/A22070335

化学学报 ›› 2022, Vol. 80 ›› Issue (11): 1476-1484.DOI: 10.6023/A22070335 上一篇下一篇

研究论文

基于氰基化9-苯基芴衍生物的激基复合物发光与性质研究

曹洪涛, 侯鹏飞, 曹庆, 李延昂, 汪莎莎^*(), 解令海^*()

南京邮电大学材料科学与工程学院/化学与生命科学学院有机电子与信息显示国家重点实验室南京 210023

投稿日期:2022-07-27 发布日期:2022-08-29
通讯作者: 汪莎莎, 解令海
基金资助:
中国博士后科学基金面上项目(2022M711684); 江苏省高校自然科学研究面上项目(22KJB430036); 江苏省低维材料化学重点实验室2021年开放课题(JSKC20022); 南京邮电大学校级自然科学基金(NY221084); 南京邮电大学校级自然科学基金(NY221085)

Exciplex Emission and Property Investigation Based on Cyano-substituted 9-Phenylfluorene Derivative

Hongtao Cao, Pengfei Hou, Qing Cao, Yanang Li, Shasha Wang(), Linghai Xie()

State Key Laboratory of Organic Electronics and Information Displays, College of Materials Science and Engineering, College of Chemistry and Life Sciences, Nanjing University of Posts & Telecommunications (NUPT), Nanjing 210023, China

Received:2022-07-27 Published:2022-08-29
Contact: Shasha Wang, Linghai Xie
About author:
†These authors contributed equally to this work.
Supported by:
China Postdoctoral Science Foundation(2022M711684); Natural Science Foundation of the Jiangsu Higher Education Institutions(22KJB430036); Open Project from Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials at Huaiyin Normal University(JSKC20022); Natural Science Foundation of Nanjing University of Posts and Telecommunications(NY221084); Natural Science Foundation of Nanjing University of Posts and Telecommunications(NY221085)

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摘要/Abstract

激基复合物发光器件因给、受体材料掺杂比例易调且易实现小的单线态-三线态能隙差等优势, 在发展工艺简单、性能高效的有机发光二极管方面显示出很大的应用潜力. 针对目前激基复合物受体材料的种类仍较为匮乏, 器件性能仍需改善等问题, 本工作设计合成出新型基于9-苯基芴的电子受体材料(TCNDPFCz)用于构筑激基复合物发光器件. 实验表明, 受体分子TCNDPFCz与给体分子1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC)掺杂后(TAPC: TCNDPFCz)呈现明显的激基复合物发光, 其光致发光效率为54%, 电流效率为27.2 cd•A^‒1, 功率效率为32.9 lm•W^‒1, 外量子效率为12.5%. 经分析, 我们推测激基复合物TAPC:TCNDPFCz形成的过程得益于TCNDPFCz具有很强的吸电子能力. 本工作表明9-苯基芴可以作为骨架单元来构筑受体分子, 为开发新型电子受体材料提供了新策略.

关键词: 9-苯基芴, 激基复合物发光, 延迟荧光, 外量子效率, 氰基取代

Exciplex-thermally activated delayed fluorescence (exciplex-TADF) devices have displayed great application potential in developing organic light-emitting diodes (OLEDs) with simple-process and high-performance, because the doped ratio of electron donor and acceptor in exciplex device is easily controlled as well as repeated, and small singlet-triplet energy splitting (ΔE_ST) can be easily achieved for harvesting TADF. However, the current reported electron acceptors are still rare, which mainly focus on traditional electron-attracting structures, such as nitrogen-heterocycles, triarylboron, triazine- arenes and diphenylphosphine oxides, etc. Therefore, it is highly desirable to construct new acceptor structures for improving exciplex device performance. In this work, we design and synthesize a novel cyano-substituted 9-phenylfluorene derivative (TCNDPFCz) as an electron acceptor to form exciplex emission through adopting 1,1-bis[(di-4-tolylamino)phenyl]-cyclohexane (TAPC) as an electron donor. Our experimental results show that the mixed system (TAPC:TCNDPFCz) exhibits bright exciplex emission at 535 nm and a favourable photoluminescence quantum yield (PLQY) of 54%. Subsequently, temperature-dependent transient fluorescence decay experiment is carried out, which indicates that the TAPC:TCNDPFCz film possesses TADF feature. It is suggested that the satisfactory PLQY value benefits from the exciplex-TADF of TAPC:TCNDPFCz. The low-temperature fluorescence and phosphorescence measurements are also performed and show that the TAPC:TCNDPFCz film displays smaller ΔE_ST value of 0.05 eV. It is obvious that such small ΔE_ST value promotes the reverse intersystem crossing from non-radiative triplet state to radiative singlet state of TAPC:TCNDPFCz, thus achieving TADF process. Additionally, electrochemical measurement shows that the TAPC:TCNDPFCz system displays large driving force of 0.41 eV in its exciplex-formation processes, which implies that the exciplex-emission (TAPC:TCNDPFCz) can be realized easily. More than that, it indicates that the acceptor TCNDPFCz possesses strong electron-accepting ability through tetracyano-substitution. An exciplex-OLED using TAPC:TCNDPFCz as the emitting layer is then fabricated, which exhibits a low turn-on voltage of 2.6 V with a maximum current efficiency of 27.2 cd•A^‒1, power efficiency of 32.9 lm•W^‒1 and external quantum efficiency of 12.5%. Therefore, the favourable photoluminescence and electroluminescence efficiencies of TAPC:TCNDPFCz are related to the strong electron-acceptability of TCNDPFCz and large driving force in the exciplex emission process. Our work suggests the 9-phenylfluorene can be used as a molecular skeleton to design new electron acceptors for exciplex-TADF.

Key words: 9-phenylfluorene, exciplex emission, delayed fluorescence, external quantum efficiency, cyano-substitution

引用此文

曹洪涛, 侯鹏飞, 曹庆, 李延昂, 汪莎莎, 解令海. 基于氰基化9-苯基芴衍生物的激基复合物发光与性质研究[J]. 化学学报, 2022, 80(11): 1476-1484.

Hongtao Cao, Pengfei Hou, Qing Cao, Yanang Li, Shasha Wang, Linghai Xie. Exciplex Emission and Property Investigation Based on Cyano-substituted 9-Phenylfluorene Derivative[J]. Acta Chimica Sinica, 2022, 80(11): 1476-1484.

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图/表 6

图式1. 本工作的分子设计思路

Scheme 1. Molecular design strategy in this work

图式2. 化合物TCNDPFCz的合成路线

Scheme 2. Synthetic route of compound TCNDPFCz

图1. (a) TAPC和(b) TCNDPFCz的化学结构; (c) TAPC, TCNDPFCz和TAPC:TCNDPFCz在薄膜状态下的吸收光谱; (d) TAPC, TCNDPFCz和TAPC:TCNDPFCz在薄膜状态下的发射光谱

Figure 1. Chemical structures of (a) TAPC and (b) TCNDPFCz; (c) UV-vis absorption spectra of TAPC, TCNDPFCz, and TAPC:TCNDPFCz in the film-state; (d) PL spectra of TAPC, TCNDPFCz, and TAPC:TCNDPFCz in the film-state

图2. (a) TAPC和TCNDPFCz薄膜的室温荧光衰减曲线(激发波长分别为335、330 nm, 检测波长分别为388、462 nm); (b) TAPC:TCNDPFCz薄膜的室温荧光衰减曲线(激发波长为355 nm, 检测波长为535 nm); (c) TAPC:TCNDPFCz薄膜的变温荧光衰减曲线(激发波长为360 nm, 检测波长为538 nm); (d) 低温荧光和低温磷光光谱(激发波长分别为340、360 nm)

Figure 2. (a) Film-state fluorescence decays of TAPC (excitation: 335 nm, detection: 388 nm) and TCNDPFCz (excitation: 330 nm, detection: 462 nm) at 300 K; (b) film-state fluorescence decays of TAPC:TCNDPFCz (excitation: 355 nm, detection: 535 nm) at 300 K; (c) film-state temperature-dependent transient fluorescence decays of TAPC:TCNDPFCz (excitation: 360 nm, detection: 538 nm); (d) film-state fluorescence (excitation: 340 nm) and phosphorescence (excitation: 360 nm) spectra of TAPC:TCNDPFCz at 77 K

图3. (a) 器件A的一般结构组成示意图; (b) 器件A在10 V电压下的发光光谱; (c) 器件A的电流密度-电压-亮度曲线; (d) 器件A的外量子效率曲线

Figure 3. (a) The general structure, (b) EL spectra at 10 V, (c) current density-voltage-luminance and (d) external quantum efficiency characteristics for device A

Device	V_turn-on^a/V	L_max^b/(cd•m^-2)	η_c^b^,^c/(cd•A^-1)	η_p^b^,^c/(lm•W^-1)	η_ext^b^,^c/%	λ_EL^d/nm	CIE^d (x, y)
A	2.6	12468	27.2, 20.1	32.9, 15.8	12.5, 9.2	556	(0.42, 0.55)

表1. 器件A的电致发光性质数据

Table 1. The electroluminescent data of device A

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基于氰基化9-苯基芴衍生物的激基复合物发光与性质研究

Exciplex Emission and Property Investigation Based on Cyano-substituted 9-Phenylfluorene Derivative

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