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N-type organic semiconductor material as well as preparation method and application thereof

A semiconductor and organic technology, applied in the field of organic optoelectronics, can solve the problems of low carrier splitting efficiency and large energy conversion efficiency gap, and achieve the effects of strong electron transport performance, high photoelectric conversion performance, and high absorption coefficient

Inactive Publication Date: 2021-02-19
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the carrier splitting efficiency of all-polymer solar cells is lower than that of organic solar cells based on n-type small molecule acceptors, resulting in a large gap in energy conversion efficiency.

Method used

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  • N-type organic semiconductor material as well as preparation method and application thereof
  • N-type organic semiconductor material as well as preparation method and application thereof
  • N-type organic semiconductor material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of Compound 10

[0041]

[0042] (1) Synthesis of compound 1

[0043] Under the protection of nitrogen, add 1-bromo-2-fluoro-4,5-xylene (10mmol) and sodium hydroxide (20mmol) into 50ml potassium permanganate aqueous solution, start stirring and heat to reflux at 100°C, and react for 10 hours . After the reaction, the product was extracted with ethyl acetate, washed three times with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the dried solution was filtered, and the solvent was spin-dried by a rotary evaporator to obtain a crude product. The crude product was separated and purified by silica gel chromatography, and the eluent was a mixed solvent of petroleum ether / ethyl acetate to obtain a solid product with a yield of 90%. 1 H NMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product.

[0044] (2) Synthesis of compound 2

[0045] Under the protection of nitrogen, compou...

Embodiment 2

[0063] Synthesis of Polymers P1~P4

[0064]

[0065]

[0066] (1) Synthesis of Polymer P1

[0067] Under nitrogen protection, compound 10 (1mmol), 2,5-bis(trimethyltin)thiophene (1mmol), tridibenzylideneacetone dipalladium (0.05mmol), tri-tert-butylphosphine (0.1mmol) were dissolved In 10 ml of chlorobenzene, react at 110° C. for 10 hours. After the reaction, the Soxhlet extraction method was used to extract with n-hexane, acetone, dichloromethane, and chloroform solvents in sequence, and finally, the solid product was obtained by chromatography in anhydrous methanol and filtered, with a yield of 90%. 1 H NMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product. figure 1 is the absorption spectrum of polymer P1, and P1 has absorption in a wide wavelength range from 300 to 900 nm.

[0068] (2) Synthesis of Polymer P2

[0069] Under nitrogen protection, compound 10 (1mmol), bis(trimethyltin)bithiophene (1mmol), t...

Embodiment 3

[0075] Synthesis of Polymer P5

[0076]

[0077] (1) Synthesis of Polymer P5

[0078] Under nitrogen protection, compound 10 (1mmol), bis-(1,5-cyclooctadiene) nickel (0.05mmol), and 2-bipyridine (0.5mmol) were dissolved in 10ml of anhydrous tetrahydrofuran, and at 80°C React for 10 hours. After the reaction, the Soxhlet extraction method was used to extract with n-hexane, acetone, dichloromethane, and chloroform in sequence, and finally, the solid product was obtained by chromatography in anhydrous methanol and filtration, with a yield of 89%. 1 H NMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product.

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Abstract

The invention discloses a halogenated n-type organic polymer semiconductor material as well as a preparation method and application thereof. Fluorine or chlorine atoms are introduced into brominated electron acceptor-electron donor- electron acceptor (A-D-A) type n-type small molecules, and the halogenated n-type organic polymer semiconductor material is further prepared through condensation polymerization. The introduction of halogen atoms can make the absorption spectrum to generate red shift, improve the absorption coefficient and electron mobility, and enable the material to have better photoelectric conversion efficiency. The halogenated n-type organic polymer semiconductor material can be applied to organic / polymer electronic devices such as organic / polymer photoelectric detectors and organic / polymer solar cells as an active layer.

Description

technical field [0001] The invention belongs to the field of organic optoelectronics, in particular to a class of halogenated n-type organic semiconductor materials and their synthesis and their application in organic / polymer electronic devices, especially in organic / polymer photodetectors and organic / polymer solar cells application. Background technique [0002] As a clean energy technology, all-polymer solar cells based on p-type polymer donors and n-type polymer acceptors have outstanding advantages such as flexibility, all-solid-state, low-cost solution processing, and translucency, as well as excellent Light, heat, and mechanical stability, showing great commercial value and application prospects. However, the carrier splitting efficiency of all-polymer solar cells is lower than that of organic solar cells based on n-type small molecule acceptors, resulting in a large gap in energy conversion efficiency. Therefore, the development of n-type polymer acceptor materials ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D513/00H01L51/30H01L51/46H01L51/54
CPCC08G61/126C07D513/00C08G2261/124C08G2261/1412C08G2261/146C08G2261/3223C08G2261/3243C08G2261/3241C08G2261/3246C08G2261/414C08G2261/514C08G2261/91C08G2261/92H10K85/113H10K85/151Y02E10/549
Inventor 应磊彭沣曹镛
Owner SOUTH CHINA UNIV OF TECH
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