一种π-桥三联蒽型深蓝光材料的合成与性能研究

doi:10.6023/cjoc202601001

有机化学 ›› 2026, Vol. 46 ›› Issue (6): 2415-2422.DOI: 10.6023/cjoc202601001 上一篇下一篇

研究论文

一种π-桥三联蒽型深蓝光材料的合成与性能研究

孙晓娟^a, 张明^b^,^*(), 田云飞^a, 王志强^a^,^*(), 郑才俊^c^,^*()

^a 洛阳师范学院化学化工学院洛阳市绿色合成与光功能材料重点实验室洛阳 471934
^b 陕西省计量科学研究院国家市场监管重点实验室(计量光学及应用) 西安 710100
^c 电子科技大学光电科学与工程学院成都 610054

收稿日期:2026-01-02 修回日期:2026-02-09 发布日期:2026-04-02
通讯作者: 张明, 王志强, 郑才俊
基金资助:
国家自然科学基金(22302088); 国家自然科学基金(62222503); 国家自然科学基金(62575056); 四川省自然科学基金(2024NSFSC0012); 四川省自然科学基金(2024NSFSC1446); 国家市场监督管理总局科技计划(2024MK126)

Synthesis and Properties of a Deep Blue Emitting Material Based on π-Bridged Teranthracene Derivative

Xiaojuan Sun^a, Ming Zhang^b^,^*(), Yunfei Tian^a, Zhiqiang Wang^a^,^*(), Caijun Zheng^c^,^*()

^a Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934
^b Key Laboratory of Metrological Optics and Application for Sate Market Regulation, Shanxi Institute Metrology Science, Xi'an 710100
^c School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China, Chengdu 610054

Received:2026-01-02 Revised:2026-02-09 Published:2026-04-02
Contact: Ming Zhang, Zhiqiang Wang, Caijun Zheng
Supported by:
National Natural Science Foundation of China(22302088); National Natural Science Foundation of China(62222503); National Natural Science Foundation of China(62575056); Sichuan Science and Technology Program(2024NSFSC0012); Sichuan Science and Technology Program(2024NSFSC1446); Technology Program of the State Administration for Market Regulation(2024MK126)

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摘要/Abstract

设计、合成了一种π-桥三联蒽型深蓝光电致发光材料2-叔丁基-9,10-二[4-(10-苯基蒽-9-基)苯基]蒽(PBTAn), 利用核磁共振氢谱和碳谱(¹H NMR和¹³C NMR)、高分辨质谱(HRMS)表征了材料结构. 理论计算显示, 该材料具有非平面的分子结构, 接近简并的电子占据轨道(HOMO, HOMO–1, HOMO–2)和电子未占轨道(LUMO, LUMO+1, LUMO+2)主要分布在三个蒽结构单元上. 材料PBTAn可发射高效率深蓝光, 在二氯甲烷溶液和掺杂薄膜中的绝对荧光量子产率分别为0.79和0.83. 该材料具有优异的热稳定性, 热分解温度和玻璃化转变温度分别达到了494和223 ℃. 利用PBTAn作为发光层材料制备了掺杂和非掺杂电致发光器件. 其中, 掺杂器件表现出了高效率的深蓝发射光, 发光峰位于440 nm, 国际照明委员会(CIE)色坐标为(0.15, 0.09), 最大外量子效率达到了4.1%. 而且, 器件效率滚降不明显, 在1000 cd•m^–2发光亮度下, 仍能保持3.8%的外量子效率.

关键词: 深蓝光材料, 蒽衍生物, 有机发光二极管, 电致发光

A deep blue electroluminescence material based on π-bridged teranthracene derivative 2-tert-butyl-9,10-bis(4-(10- phenylanthracen-9-yl)phenyl)anthracene (PBTAn) was synthesized and characterized by ¹H NMR, ¹³C NMR and HRMS. Theory calculation results show that PBTAn has a non-planar stereostructure, and the nearly degenerated highest occupied molecular orbital (HOMO, HOMO–1, HOMO–2) and lowest unoccupied molecular orbital (LUMO, LUMO+1, LUMO+2) are primarily located on the anthracene units. PBTAn shows efficient deep blue emissions both in CH₂Cl₂ solution (λ_max=424 nm) and doped film (λ_max=426 nm). The absolute photoluminescence quantum yields were measured to 0.79 and 0.83, respectively. The emission spectrum of neat PBTAn solid film (λ_max=439 nm) shows a larger red-shift compared to that acquired from CH₂Cl₂ solution and has two shoulder peaks at about 500 and 545 nm. The material PBTAn has excellent thermal stability, the decomposition temperature and glass transition temperature were measured to be 494 and 223 ℃ under N₂ atmosphere, respectively. Doped and non-doped electroluminescence devices were fabricated using PBTAn as emitter. The doped device based on PBTAn exhibits a deep blue emission at 440 nm with a CIE (Commission Internationale de l’Eclairage) coordinate of (0.15, 0.09). Meanwhile, the doped device shows high electroluminescence efficiency and low efficiency roll-off, the external quantum efficiency can reach to 4.1% and keep a higher value of 3.8% under the luminance 1000 cd•m^–2.

Key words: deep blue emitting material, anthracene derivative, organic light emitting diode, electroluminescence

引用此文

孙晓娟, 张明, 田云飞, 王志强, 郑才俊. 一种π-桥三联蒽型深蓝光材料的合成与性能研究[J]. 有机化学, 2026, 46(6): 2415-2422.

Xiaojuan Sun, Ming Zhang, Yunfei Tian, Zhiqiang Wang, Caijun Zheng. Synthesis and Properties of a Deep Blue Emitting Material Based on π-Bridged Teranthracene Derivative[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2415-2422.

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图/表 10

图式1. 材料PBTAn的合成路线

Scheme 1. Synthetic route of the material PBTAn

图1. 材料PBTAn的立体结构与分子轨道

Figure 1. Stereostructure and molecular orbitals of the material PBTAn

图2. 材料PBTAn的紫外-可见吸收和光致发光光谱

Figure 2. Normalized UV-Vis absorption and photoluminescence (PL) spectra of the material PBTAn

图3. 材料PBTAn的TGA和DSC(插图)曲线

Figure 3. TGA and DSC (inset) curves of the material PBTAn

图4. 材料PBTAn的循环伏安(CV)曲线

Figure 4. Cyclic voltammogram (CV) curve of the material PBTAn

图5. 非掺杂器件(a)和掺杂器件(b)的能级图及器件中所用材料的分子结构(c)

Figure 5. Energy level diagrams of non-doped device (a) and doped device (b), and molecular structures of materials used in devices (c)

Device	V_on^a/V	λ_max^b/nm	FWHM^b/nm	CIE (x, y)^b	L_max^c/(cd•m^–2)	EQE^d/% Max/1000	CE^d/(cd•A^–1) Max/1000	PE^d/(lm•W^–1) Max/1000
Non-doped	3.6	444	71	0.20, 0.21	3500	3.2/3.0	5.3/5.0	3.1/2.5
Doped	3.9	440	62	0.15, 0.09	2810	4.1/3.8	3.6/3.2	2.4/1.2

表1. 器件的主要电致发光性能数据

Table 1. Key electroluminescence performance data of the devices

图6. 器件的电致发光光谱

Figure 6. Electroluminescence spectra of the devices

图7. 器件的电流密度-电压-亮度特性曲线

Figure 7. Current density-voltage-luminance curves of the devices

图8. 器件的外量子效率-亮度曲线

Figure 8. External quantum efficiency-luminance curves of the devices

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一种π-桥三联蒽型深蓝光材料的合成与性能研究

Synthesis and Properties of a Deep Blue Emitting Material Based on π-Bridged Teranthracene Derivative

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