Acceptor material based on benzoxadiazole and preparation method and application of acceptor material

A technology of benzoxo group and acceptor materials, which is applied in the manufacture of semiconductor/solid-state devices, electric solid-state devices, semiconductor devices, etc., can solve the problem of polydispersity of molecular weight distribution and poor repeatability between batches, difficulty in energy level regulation, and invariable Stability and other issues, to achieve the effect of improving photoelectric conversion efficiency, narrow optical bandgap, and good solubility

Active Publication Date: 2020-04-07
深圳睿迅有机太阳能有限公司
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Problems solved by technology

However, fullerene derivatives have problems such as instability, high cost, weak absorption in the visible light region, difficulty in energy level regulation, polydispersity of molecular weight distribution and poor repeatability between batches, so scientists began to look for alternatives to them. of photovoltaic materials to suit practical production applications

Method used

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  • Acceptor material based on benzoxadiazole and preparation method and application of acceptor material
  • Acceptor material based on benzoxadiazole and preparation method and application of acceptor material
  • Acceptor material based on benzoxadiazole and preparation method and application of acceptor material

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preparation example Construction

[0061] The embodiment of the present invention also provides a preparation method of a benzoxadiazole-based acceptor material, comprising the following steps:

[0062] S10. Obtaining aldehyde compounds and electron-withdrawing compounds containing benzoxadiazole units;

[0063] S20. Obtain a weakly basic catalyst, dissolve the catalyst, the aldehyde compound and the electron-withdrawing compound in an organic solvent, and reflux at 60°C to 70°C for 12 to 24 hours to obtain a benzene-based Acceptor materials for oxadiazoles;

[0064] Wherein, the aldehyde compound containing benzoxadiazole unit is:

[0065]

[0066] The electron-withdrawing compound is selected from any one of the following compounds:

[0067]

[0068] Among them, A is selected from oxygen group elements, R 1 from C 16 ~C 30 branched chain alkyl, and the C 16 ~C 30 In the branched chain alkyl group, a branch is formed on at least one of the first three carbons adjacent to the N atom, R 2 Selected ...

Embodiment 1

[0119] A kind of preparation method of acceptor material based on benzothiadiazole, as attached figure 1 The synthetic route is shown as:

[0120] S10. to Aldehyde compounds containing benzothiadiazole units were synthesized as starting compound 1.

[0121] ①Dissolve compound 1 (5.0g, 12.4mmol) in 100mL of tetrahydrofuran, stir at room temperature, add N-bromosuccinimide (2.21g, 12.4mmol) in batches, stir and react at room temperature for 12 hours, then add 40 mL of saturated sodium sulfite solution was extracted three times with dichloromethane, and then dried over anhydrous sodium sulfate. Purify with silica gel column, use petroleum ether as eluent, and concentrate in vacuo to obtain a light yellow liquid, namely compound 2, with a yield of 90.4%. MS (EI, m / z) 481.2;

[0122] ② Dissolve compound 2 (4.0g, 8.3mmol) in 60mL of tetrahydrofuran, then cool down to -78°C, stir, and gradually add 2M lithium diisopropylamide solution 4.35mL (8.7mmol) dropwise, react at -78°C A...

Embodiment 2

[0133] A kind of preparation method of acceptor material based on benzoselenadiazole, as attached figure 2 The synthetic route is shown as:

[0134] S10. to Aldehyde compounds containing benzoselenadiazole units were synthesized as starting material compound 1.

[0135] ①Dissolve compound 1 (5.0g, 12.4mmol) in 100mL of tetrahydrofuran, stir at room temperature, add N-bromosuccinimide (2.21g, 12.4mmol) in batches, stir and react at room temperature for 12 hours, then add 40 mL of saturated sodium sulfite solution was extracted three times with dichloromethane, and then dried over anhydrous sodium sulfate. Purify with silica gel column, use petroleum ether as eluent, and concentrate in vacuo to obtain a light yellow liquid, namely compound 2, with a yield of 90.4%. MS (EI, m / z) 481.2;

[0136] ② Dissolve compound 2 (4.0g, 8.3mmol) in 60mL of tetrahydrofuran, then cool down to -78°C, stir, and gradually add 2M lithium diisopropylamide solution 4.35mL (8.7mmol) dropwise, rea...

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Abstract

The invention belongs to the technical field of organic solar cells, and in particular, relates to an acceptor material based on benzoxadiazole; a unit containing benzoxadiazole is used as an electrondonating unit, strong electron withdrawing groups rich in cyano groups are introduced to two ends of the electron donating unit to be used as electron withdrawing units, and an organic small moleculeacceptor material with an A-D-A conjugated structure is formed. The acceptor material based on benzoxadiazole and provided by the invention has wide ultraviolet visible light spectrum absorption band(350-1150 nm), narrow optical band gap (1.08 eV), strong light absorption capability, and good sunlight capturing capability; meanwhile, the acceptor material has relatively good solubility, is easily dissolved in a common organic solvent, and is applied to an organic solar cell device, so that the device has relatively high short-circuit current (9.16 mA / cm<2>), relatively high open-circuit voltage (0.74 V) and relatively high photoelectric conversion efficiency (4.41%), and the application prospect is wide.

Description

technical field [0001] The invention belongs to the technical field of organic solar cells, and in particular relates to a benzoxadiazole-based acceptor material and a preparation method thereof, and the application of the acceptor material in organic solar cells. Background technique [0002] With the increasingly serious energy problems, it is imminent to develop new energy sources, and solar energy has great development prospects due to 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 (OPV), which use organic conjugated molecules as active materials, have many advantages such as light weight, flexibility, wide source of raw materials, low cost, solution processing and large-area preparation, and are widely accepted in the global academic and industrial circles. focus on. Among them, the photosensitive active layer material is the main material that con...

Claims

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Application Information

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IPC IPC(8): C07D513/22C07D517/22H01L51/54
CPCC07D513/22C07D517/22H10K85/626H10K85/6572H10K85/657Y02E10/549
Inventor 黄佳乐艮文娟史胜斌
Owner 深圳睿迅有机太阳能有限公司
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