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Tetraphenylethylene blue-fluorescence organic compound, preparation method thereof and blue organic electroluminescence device

An organic compound, blue fluorescence technology, applied in the field of materials, can solve the problems of unfavorable carrier injection and transmission, low device efficiency, etc., and achieve the effect of inhibiting exciton annihilation, good thermal stability, and strong fluorescence emission.

Inactive Publication Date: 2018-09-14
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the device efficiency of blue OLEDs is often lower than that of green and red OLEDs due to the high energy barrier of blue fluorescent materials that is not conducive to carrier injection and transport.

Method used

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  • Tetraphenylethylene blue-fluorescence organic compound, preparation method thereof and blue organic electroluminescence device
  • Tetraphenylethylene blue-fluorescence organic compound, preparation method thereof and blue organic electroluminescence device
  • Tetraphenylethylene blue-fluorescence organic compound, preparation method thereof and blue organic electroluminescence device

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preparation example Construction

[0040] The invention provides a preparation method of a tetraphenylethylene blue fluorescent organic compound, comprising:

[0041] One of 9-(1-naphthyl)-10-anthracene boronic acid and 9-(2-naphthyl)-10-anthracene boronic acid is reacted with triphenylbromoethylene to obtain structure shown in formula (I) compound;

[0042]

[0043] Wherein, Ar is naphthyl.

[0044] In the present invention, one of 9-(1-naphthyl)-10-anthraceneboronic acid and 9-(2-naphthyl)-10-anthraceneboronic acid is reacted with triphenylbromoethylene specifically as follows: 9 One of -(1-naphthyl)-10-anthraceneboronic acid and 9-(2-naphthyl)-10-anthraceneboronic acid is mixed with triphenylbromoethylene, catalyst and base, and heated under inert gas conditions The reaction was refluxed to obtain a solid product.

[0045] Wherein, the catalyst of the reaction is preferably tetrakis(triphenylphosphine) palladium; the base of the reaction is preferably potassium carbonate; the inert gas includes but not...

Embodiment 1

[0072] A: Preparation of compound (I-1)

[0073] Weigh 1.0g of 9-(1-naphthyl)-10-anthracenboronic acid, 1.25g of triphenylbromoethylene, 1.59g of potassium carbonate, 50mL of ethylene glycol dimethyl ether and 5mL of water into a 100mL two-necked flask. Stir to remove the air in the device and protect it with nitrogen, then add 99.6 mg of tetrakis(triphenylphosphine)palladium under nitrogen flow. Heated to 80°C, condensed and refluxed for 30 hours. As the reaction progressed, the solution turned from light yellow to orange-brown. The crude product solution was extracted with dichloromethane and water, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The crude product obtained after the filtrate was distilled under reduced pressure was separated with a silica gel column, and the eluent was a mixed solvent composed of dichloromethane and petroleum ether with a volume ratio of 1:8. The resulting pure product solution was distilled under reduced pr...

Embodiment 2

[0077] OLED device fabrication

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Abstract

The invention provides a tetraphenylethylene blue-fluorescence organic compound and a preparation method for an organic electroluminescence device thereof. A structure of the tetraphenylethylene blue-fluorescence organic compound is as shown in formula (I): wherein Ar is a naphthyl. The compound is capable of enabling the naphthyl and a triphenylethylene group to be connected with anthracene, using the anthracene as a fundamental luminescence group, and using triphenylethylene and naphthalene as modification for transforming a structure or a group of the anthracene, wherein the triphenylethylene and the anthracene form a structure similar to tetraphenyl ethylene. Because the tetraphenyl ethylene structure can produce an aggregation-induced emission (AIE) effect, a phenomenon of exciton annihilation can be effectively inhibited, so a molecule has the stronger fluorescence emission in a high-concentration aggregation state than that in a low-concentration. In addition, because a relativemolecular weight of the compound is larger, an aromatic structure and an ethylene structure have a conjugate condition, the finally prepared compound is good in heat stability, and has the high luminance brightness, and the prepared device is good in performance.

Description

technical field [0001] The invention relates to the technical field of materials, in particular to a tetraphenylethylene blue fluorescent organic compound, a preparation method thereof and a blue organic electroluminescent device. Background technique [0002] The first report of organic small molecule ultra-thin multi-layer electroluminescent diode was invented by C.Tang and VanSlyke in 1987, which triggered an upsurge in the research and development of organic light-emitting diodes (OLEDs) in academia and industry. Compared with traditional lighting and display devices, OLED has many advantages such as light weight, high flexibility, wide viewing angle and high luminous efficiency. It has great application potential in the fields of flat panel display, smart phone and solid-state lighting. [0003] In OLEDs, fluorescent materials are the key substances that undertake the luminous function, so their luminous efficiency, thermal stability, luminous chromaticity and other pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/60C07C1/32C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C1/321C07C15/60C09K2211/1011C09K2211/1007C07C2603/24H10K85/615H10K50/11
Inventor 黎家涛霍延平赖卓仪刘昊籍少敏杨庆旦许宗祥孙建伟余力
Owner GUANGDONG UNIV OF TECH
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