Design and Synthesis of a Y-Type Thioxanthone-Carbazole for the Application in Blue and Yellow Organic Light-Emitting Diodes

doi:10.6023/cjoc202309026

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1210-1217.DOI: 10.6023/cjoc202309026 Previous Articles Next Articles

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一种Y型噻吨酮-咔唑分子的设计、合成及其蓝光和黄光有机发光二极管应用

孙静^a^,^b^,^*(), 樊志杰^a, 杜纪宽^a, 李硕^a, 苗艳勤^a^,^b^,^*(), 赵波^a, 董海亮^a^,^b, 王华^a^,^*()

a 太原理工大学新材料界面科学与工程教育部重点实验室太原 030024
b 山西浙大新材料与化工研究院太原 030024

收稿日期:2023-09-27 修回日期:2023-11-15 发布日期:2023-12-28
基金资助:
国家自然科学基金(62074109); 国家自然科学基金(6207031407); 国家自然科学基金委联合基金(U21A20492); 山西省科技创新人才队伍建设(202204051001013)

Design and Synthesis of a Y-Type Thioxanthone-Carbazole for the Application in Blue and Yellow Organic Light-Emitting Diodes

Jing Sun^a^,^b(), Zhijie Fan^a, Jikuan Du^a, Shuo Li^a, Yanqin Miao^a^,^b(), Bo Zhao^a, Hailiang Dong^a^,^b, Hua Wang^a()

a Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, Taiyuan University of Technology, Taiyuan 030024
b Shanxi-Zheda Institute of Advanced Materials and Chemical Engineering, Taiyuan, 030024

Received:2023-09-27 Revised:2023-11-15 Published:2023-12-28
Contact: * E-mail: sunjing@tyut.edu.cn;miaoyanqin@tyut.edu.cn;wanghua001@tyut.edu.cn
Supported by:
National Natural Science Foundation of China(62074109); National Natural Science Foundation of China(6207031407); Joint Funds of the National Natural Science Foundation of China(U21A20492); Science and Technology Innovation Talent Team Project of Shanxi Province(202204051001013)

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Abstract

A Y-shaped emitter, TX-Ph2Cz, was designed and synthesized, which uses a thioketone unit as the acceptor and 9,9'-(1,3-phenylene)bis-9H-carbazole as the donor. The compound exhibited blue emission at about 420 nm in diluted solution and a small change in the different solvents with various polarities. In the mixed tetrahydrofuran (THF)/H₂O solvents, emission bands had a red shift of 36 nm with the increased content of water. According to the single crystal structure, TX-Ph2Cz showed many intermolecular interaction and the π…π interaction between adjacent molecules would increase the intermolecular charge transfer. Critically, TX-Ph2Cz exhibited blue emission (440 nm) in the doped device, but yellow emission (540 nm) in the non-doped device was originated from the excimer of TX-Ph2Cz. Moreover, the maximum current efficiency and external quantum efficiency of non-doped device were 4.91 cd/A and 2.64%, respectively.

Key words: organic light-emitting diode (OLED), thioxanthone-carbazole derivatives, Y-type structure, excimer

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Jing Sun, Zhijie Fan, Jikuan Du, Shuo Li, Yanqin Miao, Bo Zhao, Hailiang Dong, Hua Wang. Design and Synthesis of a Y-Type Thioxanthone-Carbazole for the Application in Blue and Yellow Organic Light-Emitting Diodes[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1210-1217.

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Fig. & Tab. 10

Scheme 1. Synthesis route of the intermediates and TX-Ph2Cz

Figure 1. TGA curve and DSC curve of TX-Ph2Cz

Figure 2. CV curve of TX-Ph2Cz

Compound	λ_abs^a/nm	λ_PL/nm	T_d/℃	T_g/℃	HOMO/eV	LUMO/eV	τ^a/ns	Φ_PL^b/%	S₁/eV	T₁/eV	ΔE_ST/eV
TX-Ph2Cz	315, 339, 389	420^a/458^b	383	142	–5.13	–2.13	1.11	1.74	3.04	2.67	0.37

Table 1. Summary of thermal stability, electrochemical and photophysical properties

Figure 3. UV-vis absorption spectra (a) and PL spectra (b) of TX-Ph2Cz in different solvents (10–5 mol/L) with various polarities, PL spectrum and phosphorescence spectrum (c) at 77K in 2-methyltetrahydrofuran solution, and PL spectra (d) in the different THF/H2O solution (inset: photographs of TX-Ph2Cz)

Figure 4. Natural transition orbitals (NTO) for S0→S1 and S0→T1 transitions, TD-DFT calculated energy levels, and corresponding spin-orbit coupling constants of TX-Ph2Cz

Figure 5. Molecular structure (a) and molecular stacking (b) of TX-Ph2Cz

Figure 6. Device architecture and energy-level diagram of the functional materials (a) and PL spectra of the evaporated films (b)

Figure 7. Electroluminescent properties of TX-Ph2Cz: EL spectra at 5 V (a), J-V-L curve (b), CE-L-PE curve (c) and EQE-L curve (d)

Device	λ_EL/nm	V_on/V	L_max/(cd•m^–2)	CE_max/(cd•A^–1)	PE_max/(lm•W^–1)	EQE_max/%	FWHM/nm	CIE (x, y)
TX-Ph2Cz	540	4.5	1445	4.91	3.32	2.64	60	(0.340, 0.463)
3% TX-Ph2Cz	440	4.6	224.8	0.19	0.12	0.25	35	(0.169, 0.084)

Table 2. Summary of electroluminescent properties for TX-Ph2Cz

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一种Y型噻吨酮-咔唑分子的设计、合成及其蓝光和黄光有机发光二极管应用

Design and Synthesis of a Y-Type Thioxanthone-Carbazole for the Application in Blue and Yellow Organic Light-Emitting Diodes

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