Broad-band gap polymer donor material based on benzodithiazole electron-deficient unit and preparation method and application thereof

A benzobithiazole and wide-bandgap technology, which is applied in the field of wide-bandgap polymer donor materials and its preparation, can solve the problems of low carrier mobility, low absorption strength, and poor crystallinity, and achieve reduced steric hindrance, Improves absorption and improves crystallinity

Active Publication Date: 2021-08-13
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned deficiencies or defects, the object of the present invention is to provide a wide bandgap polymer donor material based on benzobithiazole electron-deficient units and its preparation method and application, which can effectively solve the problem of existing wide bandgap polymer donor materials. The existing problems of low absorption intensity, poor crystallinity and low carrier mobility

Method used

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  • Broad-band gap polymer donor material based on benzodithiazole electron-deficient unit and preparation method and application thereof
  • Broad-band gap polymer donor material based on benzodithiazole electron-deficient unit and preparation method and application thereof
  • Broad-band gap polymer donor material based on benzodithiazole electron-deficient unit and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A monomer BBT-Br based on a benzobithiazole electron-deficient unit containing a thiophene π bridge, the synthesis route is as follows:

[0043]

[0044] Synthesis of compound 3: 2,5-diamino-1,4-benzenedithiol dihydrochloride (2.50g, 10.2mmol) and o-dichlorobenzene (20mL) were added to a 100mL round-bottomed flask, ice Cool in a water bath to 0°C, under the protection of argon, add trimethylsilyl polyphosphate (3.5mL, 27.5mmol) and compound 3 (5.44g, 23.5mmol) in sequence, after the addition is complete, heat to 150°C and react for 24 hours , cooled to room temperature, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, suction filtered, and the dichloromethane solvent was removed by rotary evaporation, and the crude product was separated and purified by column chromatography (silica gel, eluent: petroleum ether / dichloromethane=1 / 1, v / v) to obtain 2.47 g of a colorless light yellow oily liquid with a yield of 46%. 1 H NMR (4...

Embodiment 2

[0049] A polymer donor material called PBDTF-BBT, the synthesis route is as follows:

[0050]

[0051] Synthesis of polymer PBDTF-BBT: BBT-Br (0.31g, 0.36mmol) and BDTF-Sn (0.34g, 0.36mmol) were added to a 25mL two-necked bottle, 5.5mL of degassed chlorobenzene was added, and argon protection Add tris(dibenzylideneacetone)dipalladium (6.67mg, 7.29μmol) and tris(o-methylphenyl)phosphine (8.87mg, 29.14μmol) quickly, pump and exchange gas 3 times, and react at 110°C for 6 hours , cooled to room temperature, the reaction solution was dispersed in a beaker with 300mL of methanol, and suction filtered to obtain a red solid, which was extracted by Soxhlet extraction with methanol, n-hexane, acetone, and dichloromethane to remove the catalyst and low-molecular-weight polymers. Soxhlet extraction with chloroform was used to obtain a dark red residual solid, which was placed in a beaker containing 200 mL of methanol, stirred for 30 minutes, left to stand for 2 hours, and filtered wit...

Embodiment 3

[0053] A polymer donor material called PBDTCl-BBT, the synthesis route is as follows:

[0054]

[0055] Synthesis of polymer PBDTCl-BBT: BBT-Br (0.28g, 0.33mmol) and BDTCl-Sn (0.3206g, 0.3290mmol) were added to a 25mL two-necked bottle, 5.5mL of degassed chlorobenzene was added, and argon protection Add tris(dibenzylideneacetone)dipalladium (6.03mg, 6.58μmol) and tris(o-methylphenyl)phosphine (8.01mg, 26.32μmol) rapidly, pump and exchange gas 3 times, and react at 110°C for 6 hours , cooled to room temperature, the reaction system was dispersed in a beaker with 300mL of methanol, and suction filtered to obtain a red solid, which was extracted by Soxhlet extraction with methanol, n-hexane, acetone, and dichloromethane to remove the catalyst and low-molecular-weight polymers. Soxhlet extraction with chloroform was used to obtain a deep red residual solid, which was placed in a beaker containing 200 mL of methanol, stirred for 30 minutes, left to stand for 2 hours, and filtere...

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Abstract

The invention discloses a broad-band gap polymer donor material based on a benzodithiazole electron-deficient unit and a preparation method and application thereof, and belongs to the technical field of organic optoelectronics. Benzo [1, 2-d: 4, 5-d'] dithiazole perpendicular to a polymer main chain is used as an acceptor unit and is copolymerized with a series of donor units, and a batch of high-performance wide-band gap polymer donor materials are obtained; according to the present invention, with the application of the polymer organic solar cell, the open-circuit voltage of 0.85 V, the short-circuit current density of 25.86 mA cm<-2>, the fill factor of 67.4% and the photoelectric conversion efficiency of 14.86% can be obtained without deep optimization. The broad-band gap polymer donor material has the characteristics of good crystallinity and high absorption and migration rate, and has practical application value in organic solar cells.

Description

technical field [0001] The invention relates to the field of organic photoelectric technology, in particular to a wide bandgap polymer donor material based on a benzobithiazole electron-deficient unit and its preparation method and application. Background technique [0002] The depletion of fossil energy and the environmental pollution caused by its use make the sustainable development of human beings face great challenges. The development and utilization of renewable energy has become an urgent problem to be solved. Therefore, people pay more and more attention to the development and utilization of new energy. Solar energy has the characteristics of being widely distributed, inexhaustible, clean and pollution-free, and has broad development prospects. In today's society with the rapid development of global electrification, using solar cells to convert solar energy into electrical energy is a very potential utilization method. Polymer solar cells are one of a new generati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/126C08G2261/124C08G2261/1412C08G2261/146C08G2261/149C08G2261/3223C08G2261/3243C08G2261/3246C08G2261/414C08G2261/91H10K85/113H10K85/151Y02E10/549
Inventor 彭强徐小鹏段玉伟
Owner SICHUAN UNIV
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