Tetraphenylethylene-containing organic semiconductor material, and preparation method and application thereof

An organic semiconductor, tetraphenylethylene technology, applied in the field of organic photoelectric materials, can solve the problems of non-luminescence and unfavorable fluorescence emission, etc., and achieve the effect of simple storage, excellent photoelectric performance and stable material structure

Active Publication Date: 2014-09-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most conventional luminescent materials do not emit light in the solid state due to intermolecular interactions leading to non-radiative energy conversion or the formation of species unfavorable for fluorescence emission.

Method used

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  • Tetraphenylethylene-containing organic semiconductor material, and preparation method and application thereof
  • Tetraphenylethylene-containing organic semiconductor material, and preparation method and application thereof
  • Tetraphenylethylene-containing organic semiconductor material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: Preparation of organic semiconductor material (TPE-NB) containing tetraphenylethylene

[0038]

[0039] Reaction equation (1):

[0040]

[0041](1) Intermediate 1 was prepared according to the method disclosed in the literature (J. Am. Chem. Soc. 1954, 76, 3502). The raw materials 4-bromobenzophenone and dimethyl boron fluoride were ordered directly from TCI Corporation.

[0042] (2) 4-bromobenzophenone (3.92g, 15mmol), intermediate 1 (1.75g, 5mmol) and zinc powder (1.30g, 20mmol) were added to the reaction flask, and the gas was changed three times. Inject THF (80mL) down, cool to -78°C, add TiCl dropwise 4 (1.90g, 10mmol), after the dropwise addition was completed, the reaction system was returned to room temperature, and heated under reflux at 70°C for 12h. Saturated sodium carbonate solution was added until a large amount of solids were precipitated, filtered, the filtrate was extracted with dichloromethane, concentrated and powdered, and wash...

Embodiment 2

[0044] Embodiment 2: Preparation of organic semiconductor material (TPE-PNPB) containing tetraphenylethylene

[0045]

[0046] Reaction equation (2):

[0047]

[0048] (1) Intermediate 3 was prepared according to the method disclosed in the literature (Chem.Commun.2011, 47, 6924); Intermediate 5 was prepared according to the method disclosed in the literature (Chem.Eur.J.2014, 10, 994). 4-Bromobenzophenone was ordered directly from TCI Corporation.

[0049] (2) Add 4-bromobenzophenone (3.92g, 15mmol), intermediate 3 (2.06g, 5mmol) and zinc powder (1.30g, 20mmol) into the reaction flask, pump and change gas three times, and Inject THF (80mL) down, cool to -78°C, add TiCl dropwise 4 (1.90g, 10mmol), after the dropwise addition was completed, the reaction system was returned to room temperature, and then heated under reflux at 80°C for 12h. Saturated sodium carbonate solution was added until a large amount of solids were precipitated, filtered, the filtrate was extracted...

Embodiment 3

[0052] Embodiment 3: Preparation of organic semiconductor material (TPE-DB) containing tetraphenylethylene

[0053]

[0054] Reaction equation (3):

[0055]

[0056] (1) Intermediate 6 (4,4'-dibromotetraphenylethylene) was prepared according to the method disclosed in the literature (J. Mater. Chem. 2012, 22, 232).

[0057] (2) Intermediate 6 (980mg, 2mmol) was added to the reaction flask, pumped and ventilated three times, THF (60mL) was injected under nitrogen protection, cooled to -78°C, and n-BuLi (1.6M, 2.8 mL, 4.4mmol), reacted at this temperature for 2 hours, dissolved dimethyl boron fluoride (1.18g, 4.4mmol) in THF (20mL) and added to the reaction system, and continued to react at -78°C for 1 hours, then returned to room temperature and stirred overnight. After concentrating, it was made into a powder, and was passed through a column with an eluent (petroleum ether / dichloromethane=10 / 1) to obtain the final product TPE-DB with a yield of 90%.

[0058] 1 H NMR ...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a tetraphenylethylene-containing organic semiconductor material and a preparation method thereof, and application of the material in organic photoelectric devices. The tetraphenylethylene-containing organic semiconductor material is disclosed as Formula I or II, wherein R1, R2, R3, R4 and R5 can be identical or different aromatic ring derivative groups. Different modification groups can be connected to the tetraphenylethylene to regulate the electronic or hole transmission performance of the tetraphenylethylene derivatives, so that the organic semiconductor material not only can be used as a luminescent layer, but also can be used as a luminescent layer and current carrier transmission layer, thereby obtaining the electroluminescent devices with favorable photoelectric properties, simple structure and low cost; and the organic semiconductor material has wide application prospects in the fields of organic electroluminescence, organic field-effect transistors, organic solar cells and other organic electronics.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to an organic semiconductor material containing tetraphenylethylene, a preparation method thereof and an application in organic photoelectric devices. Background technique [0002] With the rise and vigorous development of the organic electronics industry, organic optoelectronic materials have become the focus of scientific research at home and abroad because of their broad application prospects in the fields of organic electroluminescent diodes, organic solar cells, organic field effect transistors, organic lasers, and chemical sensors. And one of the hotspots of product development. However, most conventional luminescent materials do not emit light in the solid state due to intermolecular interactions leading to non-radiative energy conversion or the formation of species unfavorable for fluorescence emission. [0003] The molecular structure of tetraphenyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54H01L51/46H01L51/30
CPCY02E10/549
Inventor 唐本忠陈龙赵祖金秦安军胡蓉蓉
Owner SOUTH CHINA UNIV OF TECH
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