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Conjugated polymer containing difluoronaphthothiophenedione electron-withdrawing unit as well as synthesis method and application thereof

A technology of conjugated polymers and synthesis methods, applied in the field of polymers, can solve the problem of less materials, and achieve the effects of high mobility, good solution processing performance, and excellent photoelectric performance

Active Publication Date: 2019-05-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although there are many kinds of organic conjugated polymer materials, there are relatively few materials with wide absorption and high carrier mobility. In order to achieve more efficient photoelectric conversion efficiency, it is very important to develop new high-performance donor polymer materials. Significance

Method used

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  • Conjugated polymer containing difluoronaphthothiophenedione electron-withdrawing unit as well as synthesis method and application thereof
  • Conjugated polymer containing difluoronaphthothiophenedione electron-withdrawing unit as well as synthesis method and application thereof
  • Conjugated polymer containing difluoronaphthothiophenedione electron-withdrawing unit as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1,3-bis(2-ethylhexyl)-6,7-difluoro-5,8-bis(thiophen-2-yl)naphtho[2,3-c]thiophene-4,9-dione preparation:

[0035] (1) Under nitrogen protection, add 4,5-difluorophthalic acid 1 (4.04g, 20mmol) and a drop of N,N-dimethylformamide (DMF) into a 100mL two-necked round-bottomed flask, Oxalyl chloride (10 mL), and then add 20 mL of anhydrous dichloromethane as a solvent, and stir at room temperature for 12 hours. 2,5-bis(2-ethylhexyl)thiophene 2 (6.17 g, 20 mmol), AlCl 3 (10.67g, 80mmol), it was moved to 0°C under an ice-water bath and stirred for 30 minutes, then placed at room temperature and stirred for 3 hours. Post-processing: the reaction mixture was extracted with dilute hydrochloric acid aqueous solution and chloroform to obtain an organic phase, which was put into a one-port bottle and mixed with silica gel powder for rotary evaporation, and then purified with a silica gel column (petroleum ether: dichloromethane was selected as eluent). 4:1 (v / v)), the product 3 w...

Embodiment 2

[0042] 1,3-bis(2-ethylhexyl)-6,7-difluoro-5,8-bis(5-bromothien-2-yl)naphtho[2,3-c]thiophene-4,9 - Preparation of diketones (M1):

[0043] In a 100 mL single-necked bottle, compound 6 (0.69 g, 1 mmol) was dissolved in a mixed solvent of chloroform (30 mL) and acetic acid (30 mL), and the volume ratio of chloroform and acetic acid was 1:1. Then the one-necked flask was placed in an ice bath, and when the temperature of the reaction solution dropped to about 0°C, N-bromosuccinimide NBS (0.38 g, 2 mmol) was added batch by batch, and the reaction was stirred at room temperature for 8 hours. Post-processing: Pour the reaction solution into water, extract with dichloromethane, wash the organic layer with saturated aqueous sodium chloride solution, and dry over anhydrous magnesium sulfate. After distillation under reduced pressure, the crude product was purified by silica gel column (petroleum ether was selected as the eluent) to obtain the yellow solid product M1 (1,3-bis(2-ethylhex...

Embodiment 3

[0046] Preparation of PFPT-BDT

[0047] In the water-oxygen automatic control glove box, compound M1 (1,3-bis(2-ethylhexyl)-6,7-difluoro-5,8-bis(5-bromothiophen-2-yl)naphthol [2,3-c]thiophene-4,9-dione) (79.7mg, 0.10mmol), compound M2 (4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzene And[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethyltin) (90.5mg, 0.10mmol) and catalyst tetrakistriphenylphosphine palladium (5.86mg , 0.005mmol) was added to a 10mL microwave tube, anhydrous xylene (2.5mL) was added to dissolve, and the silica gel cap was sealed. Place the microwave tube in the microwave reactor, set the temperature program: 80°C for 2 minutes, 120°C for 2 minutes, 160°C for 2 minutes, and finally 200°C for 45 minutes. In 200mL methanol, carry out Soxhlet extraction successively with methanol, acetone, n-hexane, dichloromethane and chloroform, then add the aqueous solution of sodium diethyldithiocarbamate trihydrate (225mg, 1mmol , 100mL water), stirred at 60°C for 8 hours, remov...

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Abstract

The invention discloses a conjugated polymer containing a difluoronaphthothiophenedione electron-withdrawing unit as well as a synthesis method and application thereof, and belongs to the field of application of polymers to optoelectronic materials and devices. The conjugated polymer prepared by the method provided by the invention adopts a structure containing difluoro-substituted benzoheterocycle, and fluorine atoms and an electron donor unit form a non-bonding action, so that transmission of current carriers in a planar and rigid main chain structure is enhanced, and obtaining of high mobility is facilitated. Moreover, the conjugated polymer of this type has a wide optical band gap and is suitable for matching with a small molecular receptor with a narrow band gap to realize complementation of absorption spectra, so that the conjugated polymer can be used for manufacturing active layers of a polymer light-emitting diode device, a polymer field effect transistor and a polymer solar cell.

Description

technical field [0001] The invention relates to the field of polymers applied to optoelectronic materials and devices, in particular to a conjugated polymer containing difluoronaphthothiophenedione electron-withdrawing units. Background technique [0002] With the development of human society, the reserves of traditional non-renewable energy sources such as coal, oil and natural gas are decreasing day by day, and it is urgent to seek new energy sources for sustainable development. As a kind of green renewable energy, solar energy is inexhaustible and inexhaustible. As one of the important means to solve energy problems, organic solar cells have the advantages of easy-to-obtain materials, light weight, flexibility, and large-area preparation of thin-film devices, and have attracted widespread attention from scientists. There are many kinds of materials for the active layer of organic solar cells, their chemical structures are easy to modify, their preparation and purificatio...

Claims

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Application Information

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IPC IPC(8): C08G61/12
Inventor 应磊李康黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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