论文总字数：25285字

摘 要

有机发光二极管（OLED）又称为有机发光半导体。其原理是有机发光材料通过电场作用，使电能转化为光能的过程。近年来，人们对于显示器等设备的要求越来越高，高质量和便携成为显示器的主要研发方向。而OLED材料由于所具有的高发光效率、低能耗、快响应与轻薄等优越特性取代了LCD等材料成为了新的研究热点。

热活化延迟荧光材料（TADF材料）又叫做E型延迟荧光材料。不同于传统的荧光、磷光，TADF发光存在着两种不同的发光机理：即时荧光（PF）以及延迟荧光（DF）。即时荧光机制中，TADF材料被激发，单线态激子立即开始从S1到S0态的快速衰减，从而发出荧光；延迟荧光机制中，电激发（直接）或光激发后通过系间窜越（间接）形成的三线态激子转化为单线态激子，由于增加了这一过程使发光延迟。TADF最主要的突破在激子的利用上，25%的单线态激子发出即时荧光，75%的三线态激子发出延迟荧光，达到了100%的激子利用。除此之外，TADF材料在分子设计、合成以及成本上的优势使之成为最具潜力的有机发光材料。

本项目通过Ullmann偶联反应合成了一种二苯甲酮衍生物的树枝状TADF材料，系统地表征了二苯甲酮衍生物的光学、电化学和热性质。据文献方法以咔唑为起始原料合成了中间体3,6-二叔丁基咔唑（3）和3,6-二（3,6-二叔丁基咔唑基）-咔唑（5）。随后，4,4'-二溴二苯甲酮和3,6-二（3,6-二叔丁基咔唑基）-咔唑（5）经C-N Ullmann 偶联反应合成出最终产物t-BuTCz2BP，收率42.54%。最后，通过硅胶柱色谱法纯化产物。

关键词：TADF、非掺杂溶液处理、有机发光二极管（OLED）、二苯甲酮、发射

ABSTRACT

Organic light emitting diode (OLED) is also referred to as an organic light emitting semiconductor. The principle is that the organic luminescent material converts electrical energy into light energy through the action of an electric field. In recent years, people have been more and more demanding for devices such as displays, and high quality and portability have become the main research and development directions of displays. The superior characteristics of high luminous efficiency, low energy consumption, fast response and light weight of OLED materials have made it replace traditional materials such as LCDs.

Thermally activated delayed fluorescent materials (TADF materials) are also known as E-type delayed fluorescent materials. Unlike traditional fluorescence and phosphorescence, TADF luminescence has two different luminescence mechanisms: prompt fluorescence (PF) and delayed fluorescence (DF). In the prompt fluorescence mechanism, the TADF material is excited, and the singlet excitons immediately begin to decay rapidly from the S1 to S0 state, thereby fluorescing; in the delayed fluorescence mechanism, after electrical excitation (direct) or photoexcitation, the intersystem crossing is indirectly (indirect The formed triplet excitons are converted into singlet excitons, which are delayed by the addition of this process. The main breakthrough of TADF is the use of excitons. 25% of singlet excitons emit real-time fluorescence, and 75% of triplet excitons emit delayed fluorescence, achieving 100% exciton utilization. In addition, the molecular design, synthesis and cost advantages of TADF materials make it the most promising organic luminescent material.

In this project, a dendritic TADF material of benzophenone derivative was synthesized by Ullmann coupling reaction, and the optical, electrochemical and thermal properties of benzophenone derivatives were systematically characterized. The intermediates 3,6-di-tert-butylcarbazole (3) and 3,6-bis(3,6-di-tert-butylcarbazolyl)-carbazole were synthesized according to literature method using carbazole as starting material. Subsequently, 4,4'-dibromobenzophenone and 3,6-bis(3,6-di-tert-butylcarbazolyl)-oxazole (5) were synthesized by CN Ullmann coupling reaction to obtain the final product t- BuTCz2BP, yield 42.54%. Finally, the product was purified by silica gel column chromatography.

Key words: TADF; non-doped solution treatment; Organic light emitting diode (OLED); benzophenone; emission.

目 录

摘要 I

ABSTRACT II

第一章 绪论 1

1.1. 引言 1

1.2. 有机发光二极管 2

1.2.1. OLED的发展历史 2

1.2.2. OLED的结构 3

1.2.3. OLED的工作原理 7

1.3. 热活化延迟荧光材料 8

1.4. 设计TADF分子 9

1.4.1. 给-受体型 9

1.4.2. 激基复合物 10

1.5. 论文研究思路及内容 10

第二章 实验方法和技术 12

2.1. 有机电致发光材料表征 12

2.1.1. 光物理性能表征 12

2.1.2. 结构、形貌表征 13

2.1.3. 热重分析 13

2.1.4. 电化学性能表征 13

2.2. 器件的制备 14

2.2.1. 制备ITO基片 14

2.2.2. 制备金属电极及有机功能薄膜 14

2.2.3. 器件的封装 16

第三章 材料的合成及性质表征 17

3.1. 前言·实验技术路线 17

3.2. 实验部分 18

3.2.1. 实验仪器与试剂 18

3.2.2. 合成与讨论 20

3.3. 结果与讨论 23

第四章 结构与表征 25

4.1. 核磁图谱表征 25

4.2. 紫外-可见光谱表征 26

4.3. 荧光（PL）光谱表征 26

参考文献 28

致 谢 30

第一章 绪论

1.1. 引言

发光材料由于外加电场的作用，受到电场和电流的激发下发光的现象，称为电致发光（EL）。它可以直接进行电能向光能的转化。早期的电致发光材料通常基于无机材料，且已经在光电及显示等电子器材上有了广泛的应用，如仪器显示屏、电子广告板等。但是，由于其制作成本高昂，制备操作困难，效率很低，因此很难实现大面积高分辨率的平板显示。人们开始发掘更具潜力和优势的材料来取代无机材料。

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