Conjugated polymers based on diaromatic heterocyclic-3,7-S,S-dioxodibenzothiophene units as well as preparation method and application of conjugated polymers

A kind of technology of dioxydibenzothiophene and conjugated polymer, which is applied in the field of conjugated polymer and its preparation

Inactive Publication Date: 2017-06-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a conjugated polymer based on diaromatic heterocyclic -3,7-S, S-dioxodibenzothiophene units for the problems faced by the current polymer light-emitting diode (PLED)

Method used

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  • Conjugated polymers based on diaromatic heterocyclic-3,7-S,S-dioxodibenzothiophene units as well as preparation method and application of conjugated polymers
  • Conjugated polymers based on diaromatic heterocyclic-3,7-S,S-dioxodibenzothiophene units as well as preparation method and application of conjugated polymers
  • Conjugated polymers based on diaromatic heterocyclic-3,7-S,S-dioxodibenzothiophene units as well as preparation method and application of conjugated polymers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Methyl 1-bromo-2-quinoxalinecarboxylate

[0063] Under an argon atmosphere, add 1-bromo-2-quinoxalinecarboxylic acid (10g, 37.83mmol) into a two-necked flask, then 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 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:

[0064]

Embodiment 2

[0066] Methyl 1-boronate-2-quinoxalinecarboxylate

[0067] 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

[0070] Preparation of 3,7-dibromo-S,S-thiofluorene dioxide

[0071] (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, and washed with water. Dry over anhydrous magnesium sulfate, evaporate the solvent, and recrystallize from petroleum ether. 5.65 g of white solid was obtained, yield 75%.

[0072] (2) In a 150mL three-neck flask, add 20g of 4,4'-dibromobiphenyl, 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 recrystalli...

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Abstract

The invention discloses conjugated polymers based on diaromatic heterocyclic-3,7-S,S-dioxodibenzothiophene units as well as a preparation method and an application of the conjugated polymers. The conjugated polymers based on the diaromatic heterocyclic-3,7-S,S-dioxodibenzothiophene units are obtained through a Suzuki polymerization reaction and have better solubility, films are formed through spin-coating, ink-jet printing or printing after the polymers are dissolved with a common organic solvent, and a luminescent layer of a light emitting diode is prepared. The luminescent layer based on the polymers does not require annealing treatment during preparation of a luminescent device, 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 a diaryl heterocyclo-3,7-S,S-dioxodibenzothiophene unit, 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 light-emitting materials has become the key. [0003] However, the current organ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/54
CPCC08G61/124C08G61/126C08G2261/3142C08G2261/314C08G2261/3221C08G2261/3223C08G2261/124C08G2261/64C08G2261/512C08G2261/514C08G2261/52C08G2261/5222C08G2261/411H10K85/151
Inventor 应磊赵森郭婷杨伟彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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