Polycyclic benzothiadiazole non-fullerene acceptor material, preparation method thereof and application of material

A benzothiadiazole non-fullerene and benzothiadiazole-based technology, which is applied in the field of organic solar cell material preparation, can solve the problems of low photoelectric conversion efficiency and achieve strong visible and near-infrared light absorption performance, high photoelectricity Conversion efficiency, the effect of broadening absorption

Active Publication Date: 2019-01-04
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In view of the low photoelectric conversion efficiency of organic acceptor materials in existing organic solar cells, the first purpose of the present invention is to provide a fused-ring benzothiadiazolyl with good film-forming properties and high photoelectric conversion efficiency. Non-Fullerene Acceptor Materials

Method used

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  • Polycyclic benzothiadiazole non-fullerene acceptor material, preparation method thereof and application of material
  • Polycyclic benzothiadiazole non-fullerene acceptor material, preparation method thereof and application of material
  • Polycyclic benzothiadiazole non-fullerene acceptor material, preparation method thereof and application of material

Examples

Experimental program
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Effect test

Embodiment 1

[0080] R as mentioned above 1 for Ar for R 3 for EG is When , the preparation of the acceptor material is as follows:

[0081] (1) 4,7-dibromo-5,6-dinitrobenzothiadiazole and compound A obtain compound B through stille coupling reaction:

[0082]

[0083] Synthesis of Compound B: In a 250ml round bottom flask, weigh 4,7-dibromo-5,6-dinitrobenzothiadiazole (7.68g, 20mmol) and tributyl (6-undecylthiophene And[3,2-b]thiophen-2-yl)stannane (25.68g, 44mmol) was dissolved in 100ml of tetrahydrofuran, under the protection of argon, bistriphenylphosphine palladium dichloride (0.62g, 0.88mmol) was added in the system. The mixture was refluxed at 80°C for 20 hours. Cooled to room temperature, spin-dried THF, extracted with dichloromethane, spin-dried the solvent to obtain a crude product, separated and purified by silica gel column chromatography to obtain a red solid (10.54 g), which was compound B;

[0084] (2) Compound B, triethyl phosphite and o-dichlorobenzene carry...

Embodiment 2

[0110] R as mentioned above 1 for Ar for R 3 for EG is , the preparation of the acceptor material is as follows: (1) The experimental procedure is basically the same as that of Example 1, and Compound E is prepared according to the experimental procedure of Example 1; (2) Compound E and 5,6-difluoro-3- (Dicyanomethylene) indoketone is obtained ZYQ4 acceptor material by Knoevenagel reaction:

[0111]

[0112] Synthesis of acceptor material ZYQ4: in a 250ml round bottom flask, compound E (0.154g, 0.15mmol) and 3-(dicyanomethylene) indoketone 0.345g, 1.50mmol) were dissolved in 45ml chloroform, added 1ml of pyridine, the mixed solution was refluxed for 12 hours under the protection of argon, cooled to room temperature, poured into 200ml of anhydrous methanol, and suction filtered to obtain the crude product, which was separated and purified by silica gel column chromatography to obtain a dark blue solid (0.140g). That is, the acceptor material ZYQ4.

[0113] The yie...

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Abstract

The invention discloses a polycyclic benzothiadiazole non-fullerene acceptor material, a preparation method thereof and an application of the material. The polycyclic benzothiadiazole non-fullerene acceptor material comprises a polycyclic benzothiadiazole center core and electrophilic end groups, the polycyclic benzothiadiazole center core is of a nitrogen bridge trapezoidal polycyclic structure,the electrophilic end groups are connected to two ends of the center core, 4, 7-dibromo-5, 6-binitro benzothiadiazole serves as a raw material in the preparation process, Stille coupling and Vilsmeier-Haack reaction are sequentially performed to obtain the polycyclic benzothiadiazole center core, and end-group structures are introduced by Knoevenagel reaction to obtain the polycyclic benzothiadiazole non-fullerene acceptor material. The acceptor material is good in solubility and easily processed into a film, has a good photoelectric conversion function and is used for preparing an organic solar battery device, and photoelectric conversion efficiency reaches nearly 16% of single battery conversion efficiency.

Description

technical field [0001] The invention relates to an acceptor material for organic solar cells, in particular to a fused-ring benzothiadiazolyl non-fullerene acceptor material, and also relates to its preparation method and application in organic solar cells, belonging to organic solar cells The field of material preparation technology. Background technique [0002] With the increasingly serious energy problems, it is imminent to develop new energy sources, and solar energy has great development prospects because of its clean, non-polluting, inexhaustible and inexhaustible advantages. How to make better use of solar energy is a key solution to the energy crisis. Organic solar cells have attracted widespread attention from researchers because of their flexibility and low cost, which can be prepared at low cost. After more than 20 years of development, the current efficiency of single-layer heterojunction organic solar cells has reached 14%, and it is likely to replace traditi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/22H01L51/46
CPCC07D513/22H10K85/626H10K85/657Y02E10/549
Inventor 邹应萍张云强袁俊周流洋彭红建
Owner CENT SOUTH UNIV
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