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Conjugated polymer based on aryl heterocyclic-3-S,S-dioxodibenzothiophene unit as well as preparation method and application of conjugated polymer

A technology of dioxydibenzothiophene and conjugated polymer is applied in the field of conjugated polymer and its preparation, which can solve the problems such as the luminous efficiency and service life of light-emitting devices cannot meet practical requirements, and the development of OLED technology is limited.

Inactive Publication Date: 2017-06-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the current organic light-emitting device technology has encountered a bottleneck problem in the development process, that is, the luminous efficiency and service life of the light-emitting device cannot meet the practical requirements, which greatly limits the development of OLED technology. conducting exploratory research

Method used

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  • Conjugated polymer based on aryl heterocyclic-3-S,S-dioxodibenzothiophene unit as well as preparation method and application of conjugated polymer
  • Conjugated polymer based on aryl heterocyclic-3-S,S-dioxodibenzothiophene unit as well as preparation method and application of conjugated polymer
  • Conjugated polymer based on aryl heterocyclic-3-S,S-dioxodibenzothiophene unit as well as preparation method and application of conjugated polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Methyl 1-bromo-2-quinoxalinecarboxylate

[0065] Under an argon atmosphere, add 1-bromo-2-quinoxalinecarboxylic acid (10g, 39.83mmol) into a two-necked flask, add 100mL of methanol, then add concentrated sulfuric acid (39.06mg, 398.29umol) dropwise, and heat to 110 °C, reacted for 18h. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=3 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid with a yield of 85%. . 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product. The chemical reaction equation is as follows:

[0066]

Embodiment 2

[0068] Methyl 1-boronate-2-quinoxalinecarboxylate

[0069] Under argon atmosphere, the compound 1-bromo-2-quinoxalinecarboxylic acid methyl ester (10g, 37.72mmol) was dissolved in anhydrous tetrahydrofuran (THF), stirred at -78°C for 20 minutes, then added n-butyl Lithium (21.05g, 113.16mmol), stirred at -78°C for 2 hours, then added isopropoxy pinacol ester (9.66g, 150.88mmol), stirred at -78°C for 1 hour, and reacted at room temperature for 16 hours . The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=2 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid with a yield of 75%. . 1 H NMR, 13 CNMR, MS and elemental analysis results ...

Embodiment 3

[0072] Preparation of 3-bromo-S,S-thiofluorene dioxide

[0073] (1) In a 150 mL round bottom flask, 5 g of biphenyl was dissolved in 80 mL of dichloromethane, 11.8 g of bromosuccinimide was added at room temperature, and then reacted at room temperature for 48 hours. After the reaction, the reactant was poured into water, extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent, and then recrystallized with petroleum ether. 5.65 g of white solid was obtained, yield 75%.

[0074] (2) Add 20g of 4,4'-dibromobiphenyl to a 150mL three-necked flask, dissolve it in 50mL of chloroform, add 11.4mL of chlorosulfonic acid dropwise, keep the reaction system below 50°C, and react for 3 hours. After the reaction, the reactant was poured into 500mL of crushed ice, and the ice was melted with Na 2 CO 3 The solution was adjusted to be neutral, and the insoluble matter was filtered out, washed with water and dried, and then ...

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Abstract

The invention discloses a conjugated polymer based on an aryl heterocyclic-3-S,S-dioxodibenzothiophene unit as well as a preparation method and application of the conjugated polymer. The conjugated polymer based on the aryl heterocyclic-3-S,S-dioxodibenzothiophene unit is obtained through Suzuki polymerization reaction. The conjugated polymer based on the aryl heterocyclic-3-S,S-dioxodibenzothiophene unit, provided by the invention, has relatively good solubility; after the conjugated polymer is dissolved with a common organic solvent, the conjugated polymer is subjected to spin-coating, inkjet printing or printing to form a film, and a light emitting layer of a light emitting diode is prepared. When the light emitting layer based on the polymer is used for preparing a light emitting device, annealing treatment is not carried out, so that a preparation process is simpler.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a conjugated polymer based on aromatic heterocyclic-3-S,S-dioxodibenzothiophene units, a preparation method and application thereof. Background technique [0002] In the past three decades, organic electronics and optoelectronics industries, including organic / polymer light-emitting diodes, organic field-effect transistors, organic solar cells, etc., have developed rapidly and gradually realized industrialization. Organic electronic products have the advantages of low price, light weight and portability. Make it have great market potential. Therefore, the development of market-attractive organic electronic products has attracted the attention of many research institutions and scientific research teams in the world, and among them, the development of new efficient and stable materials has become the key. [0003] However, the current organic light-emitti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/54
CPCC09K11/06C08G61/122C08G61/124C08G61/126C08G2261/411C08G2261/5222C08G2261/52C08G2261/124C08G2261/1412C08G2261/18C08G2261/3241C08G2261/3243C08G2261/3142C08G2261/95H10K85/113
Inventor 应磊赵森郭婷杨伟彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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