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High-glass-transition-temperature hole injection material and preparation method and application thereof

A technology of hole injection material and transition temperature, which is applied in the preparation of organic compounds, preparation of amino hydroxyl compounds, organic chemistry, etc., can solve the problem of low glass transition temperature, high material solubility requirements, and insufficient thermal stability. OLED device application requirements and other issues, to achieve the effect of simple method, good solubility, and good hole transport ability

Active Publication Date: 2018-04-24
SOUTH CHINA UNIV OF TECH
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  • Application Information

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Problems solved by technology

[0003] The glass transition temperature (T g ≈67℃) is still relatively low, and the thermal stability cannot meet the application requirements of OLED devices
[0004] In addition, in perovskite solar cells, since perovskite solar cells are mainly prepared by solution processing spin coating method, not only good hole mobility and suitable HOMO energy level are required for hole transport materials, but also the material Therefore, there are few organic hole transport materials suitable for perovskite solar cells at present.

Method used

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  • High-glass-transition-temperature hole injection material and preparation method and application thereof

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Embodiment 1

[0054] The structural formula of the hole injection material of this embodiment is specifically as follows:

[0055]

[0056] The preparation method of the hole injection material XL1 with a high glass transition temperature in this embodiment includes the following steps:

[0057] Step 1: Preparation of 6-bromo-N,N-bis(4-methoxyphenyl)-2-naphthylamine (compound 1), the reaction equation is as follows:

[0058]

[0059] Dissolve p-iodoanisole (15g, 0.064mol) and 6-bromo-2-naphthylamine (3.3g, 0.015mol) in 120ml of anhydrous toluene, and quickly add CuI (0.89g, 4.67mmol) under nitrogen atmosphere, 1,10-Phenanthroline (1.232g, 6.83mmol) and sodium tert-butoxide (7g, 75mmol) were heated to 120°C, reacted for about 48h, concentrated to remove toluene, added dichloromethane and distilled water for extraction (dichloromethane and The volume ratio of distilled water is 1:1), the organic layer is dried over anhydrous magnesium sulfate, filtered, concentrated under reduced press...

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Abstract

The invention belongs to the technical field of photoelectric materials and discloses a high-glass-transition-temperature hole injection material and a preparation method and application thereof. Thestructure of the high-glass-transition-temperature hole injection material is as shown in formula I. The preparation method of the high-glass-transition-temperature hole injection material comprises:(1) subjecting paraiodoanisole and 6-bromine-2-naphthylamine to reaction to obtain a compound 6-bromine-N, N-di-(4-methoxyphenyl)-2-naphthylamine as shown in formula II; (2) subjecting the compound asshown in formula II and bis(pinacolato)diboron to reaction to obtain a compound as shown in formula III; (3) subjecting the compound as shown in formula II and the compound as shown in formula III toreaction to obtain the hole injection material. The high-glass-transition-temperature hole injection material is high in glass-transition temperature, decomposition temperature and HOMO (highest occupied molecular orbital) energy level, good in hole mobility and beneficial to hole injection and transportation. The high-glass-transition-temperature hole injection material has promising applicationprospect in photoelectric devices.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and relates to organic small molecule hole injection materials, in particular to a binaphthyl-based high glass transition temperature hole injection material and its preparation method and application in photoelectric devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have important application prospects in the fields of display and lighting. It is of great significance to develop organic functional materials with high glass transition temperature and high performance OLED. [0003] The glass transition temperature (T g ≈67°C) is still relatively low, and the thermal stability cannot meet the application requirements of OLED devices. [0004] In addition, in perovskite solar cells, since perovskite solar cells are mainly prepared by solution processing spin coating method, not only good hole mobility and suitable HOMO energy level are required for hole ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/08H01L51/50H01L51/54
CPCC07C217/84H10K85/631H10K85/626H10K85/633H10K50/17
Inventor 朱旭辉黄小兰彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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