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Electroluminescent polymer based on thiodibenzofuran-bithiophene unit and preparation method and application thereof

A technology of thiophene unit and luminescence, which is applied in the direction of circuits, electrical components, electric solid devices, etc., can solve the problems of difficult to obtain polymers and poor solubility, and achieve improved solubility, good thermal stability, and strong heat resistance Effect

Active Publication Date: 2019-05-31
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of S, S-dioxy-dibenzothiophene units is poor, and it is difficult to obtain polymers with high content; "Polymer" (Polymer) reported The color coordinates of the green light unit polymer of the triphenylamine unit are (0.27,0.56), which is different from the standard green light, and it is slightly insufficient as a full-color display material

Method used

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  • Electroluminescent polymer based on thiodibenzofuran-bithiophene unit and preparation method and application thereof
  • Electroluminescent polymer based on thiodibenzofuran-bithiophene unit and preparation method and application thereof
  • Electroluminescent polymer based on thiodibenzofuran-bithiophene unit and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: the synthesis of compound M1

[0053] Preparation of ethylthiophene-3-carboxylate

[0054] In a 500mL three-necked flask, thiophene-3-carboxylic acid (12.8g, 0.1mol) was dissolved in 200mL of methanol, and 20mL of concentrated sulfuric acid was added dropwise to the reaction solution, and after stirring at room temperature for 12 hours, the reaction was stopped, and the reaction was quenched with water , extracted with dichloromethane and dried with anhydrous magnesium sulfate, the solution was concentrated to obtain a yellow liquid, which was purified by silica gel column chromatography, and the mixed solvent of petroleum ether / dichloromethane (5 / 1, v / v) was eluting agent, yield 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:

[0055]

Embodiment 2

[0056] Embodiment 2: the synthesis of compound M2

[0057] Preparation of ethyl 2-(tributyltin)thiophene-3-carboxylate

[0058] Under the protection of an inert gas, ethylthiophene-3-carboxylate (11.9 g, 75.3 mmol) was dissolved in 250 mL of anhydrous tetrahydrofuran, and lithium diisopropylamide (LDA) with a concentration of 1.0 mol / L was slowly added dropwise Tetrahydrofuran solution (82.8mL, 82.8mmol), stirred at room temperature for 1 hour, added tributyltin chloride (26.6mL, 97.9mmol) to the reaction system, stopped the reaction, quenched the reaction with water, carried out with dichloromethane After extraction and drying with anhydrous magnesium sulfate, the solution was concentrated to obtain a khaki liquid, which was purified by silica gel column chromatography, and the mixed solvent of petroleum ether / dichloromethane (5 / 1, v / v) was used as the eluent to obtain a colorless Liquid, 95% yield. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained...

Embodiment 3

[0060] Embodiment 3: the synthesis of compound M3

[0061] Preparation of Diethyl 2,2'-(5,5-Dioxydibenzo[b,d]thienyl-3,7-yl)bis(thiophene-3-carboxylate)

[0062] Under argon atmosphere, to a 500mL three-necked flask, add ethyl 2-(tributyltin)thiophene-3-carboxylate (9.5g, 30.4mmol), 2,7-dibromo-S,S-dioxodi Benzothiophene (20.0g, 45.6mmol), tetrabutylammonium bromide (0.49g, 1.52mmol), catalyst triphenylphosphine palladium dichloride (1.76g, 1.52mmol) and 200mL toluene, stirring and heating, until temperature When stabilized at 110°C, add organic base (20mL) and K 2 CO 3 (41.95g, 0.30mol) aqueous solution 42mL, reacted for 12h. After the reaction solution was concentrated, it was purified by silica gel column chromatography, using a mixed solvent of petroleum ether and dichloromethane (3 / 1, v / v) as eluent, to obtain a light yellow solid with a yield of 60%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the ch...

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Abstract

The invention belongs to the field of organic photoelectric devices and discloses an electroluminescent polymer based on a thiodibenzofuran-bithiophene unit and a preparation method and application thereof. The thiodibenzofuran-bithiophene unit in the electroluminescent polymer is of seven-membered polycyclic structure, having good planarity, thereby facilitating injection and transport of carriers and improving photoelectric properties of the material herein; the fused ring structure imparts good rigidity to the thiodibenzofuran-bithiophene unit, heat resistance of the material can be improved, and the practical requirement on the material is met; a strongly electrically negative group-sulfone group imparts high electron-absorbing capacity to the thiodibenzofuran-bithiophene unit, and intramolecular charge transfer occurs between the strongly electrically negative group-sulfone group and an adjacent group, spectral red shift is caused, and a luminescent material with expected color coordinates is attained. The electroluminescent polymer based the thiodibenzofuran-bithiophene unit prepared by Suzuki polymerization has good solubility, can be dissolved with common organic solvents,and can be made into a light-emitting diode light-emitting layer through spin coating, inkjet printing or film printing.

Description

technical field [0001] The invention belongs to the field of organic photoelectric devices, and in particular relates to a class of electroluminescent polymers based on thiooxyfluorenothiophene units, as well as their preparation method and application. 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 mac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54H01L51/05H01L51/30
Inventor 应磊胡黎文黄飞曹镛
Owner 东莞伏安光电科技有限公司
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