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Electroluminescent polymer based on anthracene derivatives and preparation method and application thereof

A technology of anthracene derivatives and polymers, which is applied in the field of electroluminescent polymers and their preparation, can solve the problems of reducing the photoelectric performance of devices, restricting development, and not being easy to form amorphous films, and achieves increased solubility, simple preparation methods, and excellent The effect of thermal stability

Active Publication Date: 2018-10-26
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the small molecular material of anthracene is easy to crystallize, and it is not easy to form an amorphous film; and the planarity of the anthracene unit is prone to molecular stacking, resulting in fluorescence quenching, thereby reducing the optoelectronic performance of the device and limiting its further development in the optoelectronic field.
And there are few reports on the introduction of anthracene into the polymer main chain. Therefore, it is necessary to develop a class of efficient polymer materials of anthracene and its derivatives.

Method used

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  • Electroluminescent polymer based on anthracene derivatives and preparation method and application thereof
  • Electroluminescent polymer based on anthracene derivatives and preparation method and application thereof
  • Electroluminescent polymer based on anthracene derivatives and preparation method and application thereof

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preparation example Construction

[0050] Preparation of an anthracene derivative monomer M1

[0051] Preparation of ethylthiophene-3-carboxylate

[0052] In a 500mL three-neck flask, dissolve thiophene-3-carboxylic acid (12.8g, 0.1mol) in 200mL of methanol, and add 20mL of concentrated sulfuric acid (98wt%) dropwise to the reaction solution, stir at room temperature for 12 hours, and then stop the reaction , Quenched the reaction with water, extracted with dichloromethane and dried with anhydrous magnesium sulfate, the solution was concentrated to give a yellow liquid, purified by silica gel column chromatography, the mixed solvent of petroleum ether / dichloromethane (5 / 1, v / v) is eluent, and the yield is 73%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0053]

[0054] Preparation of ethyl 2-(tributyltin)thiophene-3-carboxylate

[0055] Under the protection of an ...

Embodiment 1

[0070] The preparation of embodiment 1 polymer P1

[0071] Under argon atmosphere, 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene ( 321 mg, 0.50 mmol), 2,7-dibromo-9,9-dioctylfluorene (246.8 mg, 0.45 mmol) and monomer M1 (2,9-dibromo-7,7,14,14-tetraxane Add 7,14-dihydroperylene[1,2-b:7,8-b']dithiophene) (37.4mg, 0.05mmol) into a 50ml two-necked bottle, then add 12ml refined toluene, and then add palladium acetate (2.80mg, 12.45μmol) and tricyclohexylphosphine (6.98mg, 24.90μmol), then add 3ml of tetraethylammonium hydroxide, raise the temperature to 80°C, and react for 24 hours; then add 20mg of phenylboronic acid for capping, 12 hours Afterwards, use 0.3ml bromobenzene to carry out capping again; After continuing to react for 12 hours, stop the reaction, wait until the temperature drops to room temperature, add the product dropwise in 300ml methanol for precipitation, filter, then dissolve the crude product in 20mL of toluene , with 200-300 mesh s...

Embodiment 2

[0078] The preparation of embodiment 2 polymer P5~P10

[0079] (1) Preparation of 4,7-dibromo-2,1,3-benzothiadiazole

[0080]Under dark conditions, add 2,1,3-benzothiadiazole (5.0g, 36.8mmol) and hydrobromic acid aqueous solution (100mL, 47wt%) into a 250mL three-necked flask, heat up to reflux, and then A mixture of hydrobromic acid solution and liquid bromine solution (4.8mL, 92mmol) (volume ratio 5:1) was slowly added dropwise into the dropping funnel. After 6 hours, add NaHSO 3 The aqueous solution was stirred until it was colorless to remove excess liquid bromine, and then suction-filtered with a Buchner funnel, and the filter cake was washed with deionized water and ethanol in turn. The solid was purified with a 100-200 mesh silica gel column, petroleum ether and dichloromethane at a ratio of 1 / 1 (volume ratio) as an eluent, and then further purified with chloroform solution to obtain 11.8 g of yellow needle-like crystals, yield: 80 %. 1 H NMR, 13 C NMR, MS and elem...

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Abstract

The invention discloses an electroluminescent polymer based on anthracene derivatives and a preparation method and application thereof. The electroluminescent polymer based on the anthracene derivatives are of a seven-membered fused ring structure, the good planarity is favorable for carrier injection and transport, and the photoelectric properties of a material are improved; a ring fused structure makes the anthracene derivatives have better rigidity, which is beneficial to improving the heat resistance of polymers and meeting the practical needs of the polymers. The polymer has good solubility, can be dissolved by using a common organic solvent, and adopts spin coating, inkjet printing or printing forming to obtain a light-emitting layer of a light-emitting diode.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a class of electroluminescent polymers based on anthracene derivatives and a preparation method and application thereof. Background technique [0002] Organic / polymer light-emitting diodes, organic field-effect transistors, organic solar cells and other electronic or optoelectronic industries have developed rapidly. Among them, products based on organic light-emitting diodes (OLEDs) have already come out, but because the current preparation of OLED devices uses vacuum evaporation process , expensive equipment. The material utilization rate is low (~20%), which makes the price of OLED products remain high. Solution processing technology can make up for the deficiency of vacuum evaporation, and gradually attracts the attention of scientific research institutions and companies. Polymers have the advantages of good film-forming properties and machinabili...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/54H01L51/56C09K11/06
CPCC09K11/06C08G61/02C08G61/123C08G61/126C08G2261/1434C08G2261/141C08G2261/124C08G2261/3243C08G2261/3142C08G2261/592C08G2261/5222C08G2261/411C08G2261/3246C08G2261/64C08G2261/92C08G2261/95C09K2211/1483C09K2211/1458C09K2211/1433C09K2211/1416H10K85/113H10K71/00
Inventor 应磊郭婷胡黎文彭俊彪
Owner SOUTH CHINA UNIV OF TECH
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