High-performance hole transport material and preparation method and application thereof

A hole transport material, high-performance technology, applied in the field of organic small molecule optoelectronic materials, can solve the problems of not meeting the requirements of thermal stability and film-forming properties of materials, affecting the life of OLEDs, low glass transition temperature, etc. The effect of enhanced morphology stability, improved film morphology stability, and increased glass transition temperature

Active Publication Date: 2020-06-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the common organic small molecule hole transport materials in OLEDs are TPD (T g ≈58℃), TAPC(T g ≈79℃) and NPB(T g ≈98℃), etc. However, the common problem of these materials is that the glass transition temperature is low, which affects the life of OLEDs, and cannot meet the industrial requirements for thermal stability and film formation of materials, thus limiting its industrialization. application
Designing and synthesizing small organic molecule hole-transporting materials with both high glass transition temperature and good hole mobility is challenging
[0004] In addition, in perovskite solar cells, commonly used hole transport materials are PTAA and spiro-OMeTAD, but the cost of the two materials is relatively high, and the price is relatively expensive, so it is necessary to further develop low-cost and high-efficiency perovskite holes. hole transport material

Method used

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  • High-performance hole transport material and preparation method and application thereof
  • High-performance hole transport material and preparation method and application thereof
  • High-performance hole transport material and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0056] The structural formula of the small organic molecule hole transport material of the present embodiment is specifically as follows:

[0057]

[0058] The preparation method of the hole transport material A-1 with a high glass transition temperature in this embodiment comprises the following steps:

[0059] Step 1: Preparation of 6-bromo-N-phenyl-2-naphthylamine (compound II), reaction equation:

[0060]

[0061] P-toluenesulfonic acid (1.7g, 9mmol), aniline (12.6g, 0.135mol) and 6-bromo-2-naphthol (10.0g, 0.045mol) were dissolved in 10ml of p-xylene, heated to React at 190°C for 7 hours, then lower the temperature to 70°C, add an appropriate amount of sodium acetate (just to make the reaction system alkaline) and 100ml of ethanol and continue stirring for 10 minutes, then distill the reaction solution under reduced pressure to remove the solvent, then add warm water to stir, Suction filtration was then carried out, and the filter cake was reflux washed with ethano...

Embodiment 2

[0088] The structural formula of the small organic molecule hole transport material of the present embodiment is as follows:

[0089]

[0090] The preparation method of the small organic molecule hole transport material A-2 of this embodiment:

[0091] Step 1: Preparation of 6-bromo-N-phenyl-2-naphthylamine (II), reaction equation:

[0092]

[0093] Step (1) is exactly the same as step (1) in embodiment 1, no longer repeat them;

[0094] Step 2: Preparation of N-(6-bromonaphthalene-2-yl)-9-methyl-N-phenyl-9H-carbazol-3-amine (5), reaction equation:

[0095]

[0096] The difference between the operation process of step (2) and step (2) of embodiment 1 is that one of the reactants 2-iodo-9,9-dimethyl-9H-fluorene of step (2) in embodiment 1 uses 3 -Iodine-9-methyl-9H-carbazole instead, the column chromatography separation developer initially uses petroleum ether, after the unreacted 3-iodo-9-methyl-9H-carbazole is removed, the developer Change to a mixed solvent of pe...

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Abstract

The invention belongs to the technical field of small organic molecule photoelectric materials, and discloses a high-performance hole transport material and a preparation method and application thereof. The structure of the hole transport material is shown as a formula I, and Ar1 and Ar2 are independently an unsubstituted or substituted carbazole unit, a fluorene unit, a dibenzopyran unit and a dibenzothiophene unit, and the substituted substituent group is alkyl, alkoxy or alkylthio with the carbon atom number of 1-6. The hole transport material provided by the invention has the advantages ofhigh glass transition temperature, low HOMO energy level and good hole mobility. The invention also discloses a preparation method of the hole transport material. The method is simple and low in cost. The hole transport material provided by the invention is used for preparing photoelectric devices, especially such as OLED devices and solar cell devices.

Description

technical field [0001] The invention belongs to the technical field of organic small molecule optoelectronic materials, relates to organic small molecule hole transport materials, in particular to a low-cost, low HOMO, high glass transition temperature hole transport material and its preparation method and application in optoelectronic devices . Background technique [0002] Organic small molecule hole transport materials play an important role in the field of optoelectronic devices. Organic light-emitting diodes (OLEDs) have important application prospects in the fields of display and lighting. Solar cells are one of the research hotspots, especially perovskite solar cells, whose photoelectric conversion efficiency has exceeded 23%. [0003] At present, the common organic small molecule hole transport materials in OLEDs are TPD (T g ≈58℃), TAPC(T g ≈79℃) and NPB(T g ≈98℃), etc. However, the common problem of these materials is that the glass transition temperature is l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/68C07D209/88C07D307/91C07D333/76C07D409/12C07D405/12H01L51/00H01L51/50H01L51/54H01L51/42H01L51/46
CPCC07C211/61C07C209/68C07F5/025C07C209/10C07C209/18C07D209/88C07D307/91C07D333/76C07D409/12C07D405/12C07C2603/18H10K85/636H10K85/633H10K85/615H10K85/6576H10K85/6574H10K30/00H10K85/6572H10K50/15Y02E10/549Y02P70/50
Inventor 朱旭辉黄小兰彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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