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

doi:10.6023/A22070335

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (11): 1476-1484.DOI: 10.6023/A22070335 Previous Articles Next Articles

Article

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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Abstract

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

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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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Fig. & Tab. 6

Scheme 1. Molecular design strategy in this work

Scheme 2. Synthetic route of compound TCNDPFCz

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

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

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)

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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