Benzimidazole Acceptor (A)-π-Donor (D) Type Small Molecule Blue Purple Traditional Fluorescent Material

doi:10.6023/cjoc202501017

Abstract

Two acceptor (A)-π-donor (D) type pure organic blue purple traditional fluorescent materials with benzimidazole receptors were synthesized through C—N coupling reaction. The molecular structure of the material was confirmed using ¹H NMR, ¹³C NMR, and HRMS. The photophysical properties, thermal stability, and electrochemical properties of the material were systematically studied, and theoretical calculations were performed. The research results show that two traditional blue purple fluorescent materials with CIE_y<0.06 have been successfully synthesized, and both have good luminescence performance, thermal stability, and carrier transport characteristics. Specifically, these compounds emit strong blue purple light in solution with optical bandgap values (E_g) of 3.17 and 3.41 eV, respectively. The triplet states (T₁) energy level test are equal to 2.92 and 2.81 eV, and the absolute fluorescence quantum yields (PLQY) are 74.33% and 81.67%, respectively. The average fluorescence lifetime (τ) is as high as 2.2 ns, and the highest thermal decomposition temperature (T_d) can reach 436 ℃. The glass transition temperature (T_g) is equal to 92 ℃, and no crystallization temperature (T_c) is observed. The highest occupied molecular orbitals. The highest occupied molecular orbital (HOMO) energy levels are －5.49 and －5.71 eV, respectively. These data show that using these two materials as luminescent materials and host materials through vacuum evaporation method is expected to achieve high-performance organic light-emitting diode (OLED) devices with high efficiency and long lifespan.

Key words: benzimidazole, acceptor (A)-π-donor (D), pure organic small molecule blue purple traditional fluorescent material, luminescent properties, organic light-emitting diode (OLED)

Cite this article

Xiaomei Jiang, Haijun Tan, Liwen Ping, Zhenguang Hu. Benzimidazole Acceptor (A)-π-Donor (D) Type Small Molecule Blue Purple Traditional Fluorescent Material[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2896-2906.

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Fig. & Tab. 8

Scheme 1. Synthetic routes of target compounds TBPBI-DPA and TBPBI-Cz

Figure 1. (a) UV spectra (1.0×10－5 mol/L) of TBPBI-DPA and TBPBI-Cz in dichloromethane, as well as their PL spectra in dichloromethane (1.0×10－5 mol/L) and in the solid state, and (b) CIE chromaticity coordinates of compounds TBPBI-DPA and TBPBI-Cz in dichloromethane and solid state

Figure 2. PL spectra of (a) TBPBI-DPA and (b) TBPBI-Cz in different solvents (1.0×10－5 mol/L)

Figure 3. Fluorescence and phosphorescence spectra of TBPBI-DPA and TBPBI-Cz in (a) 2MeTHF (77 K, 1.0×10－5 mol/L) and DCM at room temperature (1.0×10－5 mol/L)

Compound	Ф_PLQY^a/%	τ^a/ns	K_r^b/s^－1	K_nr^b/s^－1
TBPBI-DPA	74.33	2.20	3.38×10⁸	1.17×10⁸
TBPBI-Cz	81.67	1.52	5.37×10⁸	1.21×10⁸

Table 1. Photophysical data of TBPBI-DPA and TBPBI-Cz

Figure 4. (a) TGA curves and (b) DSC curves of TBPBI-DPA and TBPBI-Cz

Figure 5. CV curves of TBPBI-DPA and TBPBI-Cz

Figure 6. HOMO and LUMO electron cloud distributions and corresponding energy levels of TBPBI-DPA and TBPBI-Cz

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苯并咪唑类受体(A)-π-供体(D)型小分子蓝紫色传统荧光材料