Synthesis and Exciplex Emission of a Tricyano-substituted 9-Phenylfluorene Compound

doi:10.6023/cjoc202401024

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2595-2602.DOI: 10.6023/cjoc202401024 Previous Articles Next Articles

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一种三氰基取代的9-苯基芴化合物的合成及其激基复合物发光

曹洪涛^a, 曹庆^a, 胡杨军^a, 余梓萌^a, 解鑫淼^a, 常永正^a^,^*(), 侯鹏飞^a^,^*(), 汪莎莎^a, 解令海^a^,^b^,^*()

a 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
b 河南大学柔性电子学院/河南省柔性电子产业技术研究院郑州 450046

收稿日期:2024-01-18 修回日期:2024-03-24 发布日期:2024-04-24
基金资助:
国家自然科学基金(62288102); 国家自然科学基金(22275098); 中国博士后科学基金面上项目(2022M711684); 国家留学基金(202008320051); 江苏省高等学校基础科学(自然科学)研究面上项目(22KJB430036); 及南京邮电大学校级自然科学基金(NY221084); 及南京邮电大学校级自然科学基金(NY221085); 及南京邮电大学校级自然科学基金(NY222157)

Synthesis and Exciplex Emission of a Tricyano-substituted 9-Phenylfluorene Compound

Hongtao Cao^a, Qing Cao^a, Yangjun Hu^a, Zimeng Yu^a, Xinmiao Xie^a, Yongzheng Chang^a(), Pengfei Hou^a(), Shasha Wang^a, Linghai Xie^a^,^b()

a 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, Nanjing 210023
b School of Flexible Electronics and Henan Institute of Flexible Electronics, Henan University, Zhengzhou 450046

Received:2024-01-18 Revised:2024-03-24 Published:2024-04-24
Contact: *E-mail: iamyzchang@njupt.edu.cn; 52274300048@stu.ecnu.edu.cn; iamlhxie@njupt.edu.cn
Supported by:
National Natural Science Foundation of China(62288102); National Natural Science Foundation of China(22275098); China Postdoctoral Science Foundation(2022M711684); State Scholarship Fund of China Scholarship Council(202008320051); Natural Science Foundation of the Jiangsu Higher Education Institutions(22KJB430036); Natural Science Foundation of Nanjing University of Posts and Telecommunications(NY221084); Natural Science Foundation of Nanjing University of Posts and Telecommunications(NY221085); Natural Science Foundation of Nanjing University of Posts and Telecommunications(NY222157)

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Abstract

Exciplex-emitters are attractive due to their distinct feature of easily achieving small singlet-triplet energy splitting for thermally activated delayed fluorescence (TADF), but face with challenges in convenient design of electron acceptors. New 9-phenylfluorene-based acceptor 9-[6-(2-cyano-7-isocyano-9-phenyl-9H-fluoren-9-yl)-9-ethyl-9H-carbazol-3-yl]-9-phenyl- 9H-fluorene-2,7-dicarbonitrile (TriCNDPFCz) was designed and synthesized through tricyano-substitution. By mixing TriCNDPFCz with conventional donor 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), bright exciplex-TADF was obtained with a maximum current efficiency of 46.7 cd•A^－1, power efficiency of 52.3 lm•W^－1 and external quantum efficiency of 14.5%. The experimental characterizations indicate that tricyano-substitution in 9-phenylfluorene skeleton can form strong electron-accepting ability, which is useful and convenient for constructing electron acceptor in exciplex emission.

Key words: 9-phenylfluorene, cyano-substitution, asymmetric modification, exciplex emission

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Hongtao Cao, Qing Cao, Yangjun Hu, Zimeng Yu, Xinmiao Xie, Yongzheng Chang, Pengfei Hou, Shasha Wang, Linghai Xie. Synthesis and Exciplex Emission of a Tricyano-substituted 9-Phenylfluorene Compound[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2595-2602.

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Fig. & Tab. 7

Scheme 1. Molecular design strategy in this work

Scheme 2. Synthetic routes of compound TriCNDPFCz Reagents and conditions: (a) 2-bromo-9-phenyl-9H-fluorene-9-ol, BF3? OEt2, CH2Cl2, 30 ℃, 5 h; (b) K4Fe(CN)6?3H2O, Pd(dppf)Cl2, Na2CO3, TBAB, DMF, 150 ℃, 24 h

Figure 1. Chemical structures of (a) TAPC, and (b) UV-Vis ab- sorption and (c) PL spectra of TAPC, TriCNDPFCz and TAPC: TriCNDPFCz in the film-state

Figure 2. (a) Fluorescence decays of TAPC (excitation: 335 nm, detection: 388 nm) and TriCNDPFCz (excitation: 375 nm, detection: 463 nm) and (b) fluorescence decay of TAPC:TriCNDPFCz (excitation: 375 nm, detection: 535 nm) in film-state at 300 K, (c) temperature-dependent transient fluorescence decays of TAPC:TriCNDPFCz (excitation: 375 nm, detection: 535 nm) in film-state and (d) fluorescence (excitation: 350 nm) and phosphorescence (excitation: 350 nm) spectra of TAPC:TCNDPFCz in film-state at 77 K

Emitter	λ_PL,max^a/nm	Φ_p^a/%	S₁^b/eV	T₁^b/eV	ΔE_ST/eV	Decay time^a
Emitter	λ_PL,max^a/nm	Φ_p^a/%	S₁^b/eV	T₁^b/eV	ΔE_ST/eV	τ/ns	χ²
TAPC	388	12	4.05	3.11	0.94	0.9 (45%), 4.0 (55%)	0.959
TriCNDPFCz	463	22	3.15	2.51	0.64	35.7 (100%)	0.984
TAPC:TriCNDPFCz	535	59	2.63	2.60	0.03	42.0 (40%), 230.9 (60%)	0.998

Table 1. Photophysical properties of the deposited films of TAPC, TriCNDPFCz and TAPC:TriCNDPFCz

Figure 3. (a) General structure, (b) EL spectra at 10 V, (c) current density-voltage-luminance and (d) current efficiency-luminance-power efficiency characteristics of device I

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_p^b^,^c/%	λ_El^d/nm	CIE^d
I	2.5	20363	46.7, 33.5	52.3, 32.1	14.5, 10.4	544	(0.41, 0.55)

Table 2. Summary of electroluminescence performance for device I

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一种三氰基取代的9-苯基芴化合物的合成及其激基复合物发光

Synthesis and Exciplex Emission of a Tricyano-substituted 9-Phenylfluorene Compound

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