基于三嗪的热激活延迟荧光材料的合成及性能研究

论文总字数：35731字

摘 要

近年来目前，OLED 是有机光电子领域的研究热点，由于其自发射性能强，响应时间短，视角广，高对比度，质量轻等优点，在下一代平板显示和固体照明技术中，具有广阔的应用前景。而用热激活延迟荧光（TADF） 材料代替有机贵金属配合物，可以大大降低有机电致发光器件的成本。因此设计并合成出具有高效率的热激活延迟荧光（TADF） 材料具有十分重要的意义。

咔唑分子由于其高的三线态能级，良好的空穴载流子传输性能和较好的结构可修饰性，是发光材料中常用的发光基团，三嗪和苯氰基团是典型的缺电子基团，具有电子传输性能，在环上引入空穴传输基

团咔唑，就能得到分子内电荷转移(ICT)的双极分子。

本文是以1,3,5-三嗪和苯氰为电子传输基团，通过在1,3,5-三嗪的2,4,6位引入空穴传输基团N-苯基咔唑基团和苯嗪的2,3,4位引入苯基基团，设计并合成出四个基于苯嗪和三嗪的衍生物，并通过核磁共振氢谱对其结构进行了表征。且这四个目标化合物均未见文献报道。

以咔唑、3-溴苯腈、苯基咔唑、苯嗪为起始原料，经过溴代、酯化、Suzuki 交叉偶联、环合等得目标产物。利用紫外分光光度法（UV）、荧光分光光度法（PL）研究了化合物的光物理性质。目标化合物在有机溶剂中溶解度好，可用作OLED器件发光材料。

关键词：OLED；热激活延迟荧光；咔唑；三嗪；Suzuki 交叉偶联；

Synthesis , Properties of Thermal Activation On Triazine and Triazine group Delayed Fluorescence Material

Abstract

Recently , OLED is a hot topic in the field of organic optoelectronics, due to its strong performance since launch, short response time, wide viewing angle, high contrast, light weight, etc., in the next generation of flat panel displays and solid-state lighting technology, has broad application prospects. The thermally activated delayed fluorescence (TADF) material instead of the organic precious metal complex, can greatly reduce the cost of organic electroluminescent devices. Therefore, a highly efficient synthesis of heat-activated delayed fluorescence (TADF) material is a focus of this paper.

Carbazole molecule due to its high triplet energy level, good hole carrier transport properties and good structure can be modified, and is commonly used in light-emitting material luminescent groups, triazine and benzene piperazine groups are typical electron deficient group having electron transport properties, the introduction of the hole transport groups on the carbazole ring, you can get intramolecular charge transfer (ICT) bipolar molecules.

This article is based on 1,3,5-triazine and benzene piperazine basis for the design, by introducing a 1,3,5-triazine 2,4,6 site for electronic N- phenylcarbazole triazine group and benzene 2,3,4-positions phenylcarbazole groups, based on the design and synthesis of four benzene and triazine derivatives, and by proton nuclear magnetic resonance spectroscopy, infrared spectroscopy and its structure was characterized. And this four goals compounds were not reported.

Carbazole, 3 bromoxynil, phenylcarbazole, benzene hydrochloride as a starting material, after phenyl-substituted, brominated, esterification and cyclization to give the desired product. By ultraviolet spectrophotometry (UV), fluorescence spectrophotometry (PL) studied the photophysical properties of the compounds. The results show that the maximum absorption wavelength of these compounds by UV at 250nm, maximum fluorescence emission wavelength of 360-450nm, the title compound solubility in an organic solvent, and can be used as a light emitting device OLED material.

Keywords: OLED； TADF；carbazole；triazine；Suzuki reaction ；

目录

摘要 I

Abstract II

第一章 引言 1

1.1 研究背景 1

1.2 文献综述： 1

1.3 当前存在的问题： 5

1.4 论文研究内容 5

第二章 基于氰基的的双极磷光主体材料的合成及性能研究 7

2.1 引言 7

2.2实验部分 7

2.2.1试剂和仪器 7

2.2.2氰基衍生物的合成 8

2.3 结果与讨论 10

2.3.1 材料的合成及表征 10

2.3.2 荧光发射光谱 10

2.3.3紫外-可见(UV-vis)吸收光谱 13

2.3.4电化学测试 13

2.3.5理论计算 15

2.4 结论 16

第三章 基于三嗪的热激活延迟荧光材料的合成及性能研究 17

3.1 引言 17

3.2 实验部分 17

3.2.1试剂和仪器 17

3.2.2 2,4,6-三苯基-1,3,5-三嗪衍生物衍生物的合成 18

3.3 结果与讨论 22

3.3.1 化合物的合成及表征 22

3.3.2理论计算 22

3.3.3热力学性质 24

3.3.4 电化学测试 24

3.3.5 紫外-可见(UV-vis)吸收光谱 25

3.3.6 荧光发射光谱和磷光发射光谱的测定 26

3.3.7 延迟荧光性能 28

3.4结论 30

第四章 结论和展望 32

4.1 研究结论 32

4.2 研究展望 32

本科阶段取得的成果 33

致谢 34

参考文献 35

附录 化合物的结构表征图 39

1. 引言

1.1 研究背景

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