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Fluorine-containing carbazole based conjugated polymer, preparation method and application thereof in organic optoelectronic devices

A technology of conjugated polymers and optoelectronic devices, which is applied in the direction of electric solid-state devices, electrical components, semiconductor devices, etc., and can solve problems such as high short-circuit current and fill factor, material aging, stability of materials and devices, and insufficient lifespan.

Inactive Publication Date: 2015-05-20
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these studies did not give an explanation for the higher short-circuit current and fill factor of the material in photovoltaic devices after the introduction of fluorine atoms.
Furthermore, the introduction of fluorine atoms is mostly on the acceptor units of these materials. It is true that this will enhance the electron-withdrawing ability of the acceptor units, thereby bringing about more effective intramolecular charge transfer. However, according to the molecular orbital hybridization theory, The HOMO energy level of the polymer depends on the HOMO energy level of the donor to a greater extent, and there is little research on the introduction of fluorine atoms into the donor unit
At the same time, the donor unit of the alternating copolymer of donor and acceptor is more likely to be oxidized and cause the aging of the material. The introduction of fluorine atoms on the donor should significantly improve the stability of the material, thereby prolonging the service life of the material. The research on device stability and lifetime is not deep enough

Method used

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  • Fluorine-containing carbazole based conjugated polymer, preparation method and application thereof in organic optoelectronic devices
  • Fluorine-containing carbazole based conjugated polymer, preparation method and application thereof in organic optoelectronic devices
  • Fluorine-containing carbazole based conjugated polymer, preparation method and application thereof in organic optoelectronic devices

Examples

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Embodiment 1

[0009] Example 1: The structure of the preparation formula is 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-difluoro -Synthesis of N-octylcarbazole (M2)

[0010] Add 0.30g of 2,7-dibromo-3,6-difluoro-N-octylcarbazole, 0.40g of pinacol diborate, 0.37g of potassium acetate into 20mL of DMF, and add 25.9mg of catalyst after filling and degassing carefully PdCl 2 (dppf), heated to 80° C. and stirred for three days under a nitrogen atmosphere. After the system was cooled, saturated brine and ethyl acetate were added to the system for extraction. Extracted three times with ethyl acetate, combined the organic phase, and washed the organic phase again with saturated brine, and finally washed with anhydrous Na 2 SO 4 The organic phase is dried. The solvent was removed by rotary evaporation under reduced pressure, and the obtained crude product was quickly separated by silica gel chromatography (petroleum ether 60-90° C. / ethyl acetate=4 / 1 volume ratio). A light yellow s...

Embodiment 2

[0011] Example 2: Preparation of poly[3,6-difluoro-N-octyl-2,7-carbazole-alternating-5,5-(4',7'-di-2-thienyl- 5',6'-dioctyloxy-2',1',3'-benzothiadiazole)]

[0012] 200.0 mg monomers M1 and 158.78 mg M2, 45 mL THF, 15 mL toluene, 4 mL water, and 0.4 g NaHCO 3 In a 100ML slit-gate flask of the mixture, add 3.6mg of Pd (PPh 3 ) 4 Before and after, the nitrogen gas was repeatedly filled and degassed, and then the system was stirred and refluxed for 72 hours under a nitrogen atmosphere. Then cool the system, add 10mg phenylboronic acid and 1.8mg Pd(PPh 3 ) 4 Raise the temperature and react for 4 hours, then cool down and add 100 μL of bromobenzene to raise the temperature and continue the reaction overnight to complete capping. After the system was cooled to room temperature, water and chlorobenzene were added; the organic layer was separated with a separatory funnel and washed three times with water. Then heat the organic phase to 100°C to dissolve part of the precipitated p...

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Abstract

The invention discloses a fluorine-containing carbazole based conjugated polymer, a preparation method and application thereof in organic optoelectronic devices. At present, in donor-acceptor alternating copolymers, a donor unit is more easily oxidized so as to result in material aging, and introduction of fluorine atoms into the donor unit is rarely studied yet. At the same time, introduction of fluorine atoms to the donor is supposed to significantly improve the material stability, thereby prolonging the service life of the material. The invention relates to the fluorine-containing carbazole based conjugated polymer, a preparation method and application thereof in organic optoelectronic devices. The general formula is shown as formula I. The fluorine-containing carbazole based conjugated polymer provided by the invention has very good planarity, low HOMO energy level, and excellent sun light capture ability and hole transmission capability. The conjugated polymer solution has good processability, thermal stability, charge transport, and light absorption, and is an ideal organic semiconductor material for organic electronic devices like solar cells, field-effect transistors and light-emitting diodes. The general formula is shown as the specification. (formula I).

Description

technical field [0001] The invention belongs to the fields of polymer solar cell material research and organic field effect transistor material research, and particularly relates to a class of fluorine-containing carbazole-based conjugated polymers, its preparation method and its application in organic optoelectronic devices. As a green and renewable energy utilization method, organic solar cells have the advantages of low price, light weight, and easy large-area flexible preparation, so they are favored by researchers. Bulk heterojunction solar cells based on organic conjugated materials have made great progress. A series of new materials have been synthesized and utilized, and the energy conversion efficiency has reached 12.0%, showing the broad application prospects of organic solar cells. Background technique [0002] In addition to improving the photoelectric conversion efficiency of organic solar cells, how to extend the life of organic solar cells will be a problem th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/54
Inventor 李翠红危和狄薄志山
Owner BEIJING NORMAL UNIVERSITY