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Acceptor material based on benzoimide, and preparation method and application of acceptor material

A technology of benzimide and acceptor materials, which is applied in semiconductor/solid-state device manufacturing, electric solid-state devices, semiconductor devices, etc., can solve the problems of narrow absorption band, wide optical bandgap, weak absorption, etc., and increase space Twisting, reducing the optical bandgap, reducing the effect of aggregation

Active Publication Date: 2020-04-07
深圳睿迅有机太阳能有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of acceptor material based on benzimide, aiming at solving the technical problems such as the narrow absorption band of ultraviolet-visible light spectrum of existing acceptor material used in organic solar cells, weak absorption, wide optical band gap, etc.

Method used

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  • Acceptor material based on benzoimide, and preparation method and application of acceptor material
  • Acceptor material based on benzoimide, and preparation method and application of acceptor material
  • Acceptor material based on benzoimide, and preparation method and application of acceptor material

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preparation example Construction

[0062] The embodiment of the present invention also provides a preparation method of a benzimide-based acceptor molecule, comprising the following steps:

[0063] S10. Obtaining an aldehyde compound and an electron-withdrawing compound based on benzimide;

[0064] S20. Obtain a weakly basic catalyst, dissolve the catalyst, the aldehyde compound based on benzimide, and the electron-withdrawing compound in an organic solvent, and reflux for 12 under the condition of 60° C. to 70° C. ~24 hours, get the acceptor molecule based on benzimide;

[0065]Wherein, the aldehyde compound based on benzimide is selected from:

[0066] Compound BH or compound NH

[0067] The electron-withdrawing compound is selected from any one of the following compounds:

[0068]

[0069] Among them, R 1 , R 2 , R 3 are independently selected from C 6 ~C 30 The alkyl chain of, Y is selected from sulfur or selenium, R 4 selected from any one of hydrogen, fluorine, chlorine, cyano, methoxy, su...

Embodiment 1

[0129] A kind of preparation method of acceptor molecule BH-CN based on benzimide, as attached figure 1 The synthetic route is shown as:

[0130] S10. Compound A 1 Synthesis of aldehyde compound BH based on benzimide as starting material.

[0131] ①Compound A 1 (4.3g, 10.3mmol) was dissolved in concentrated sulfuric acid / fuming nitric acid (30mL / 75mL), refluxed at 90°C for 15 hours, then cooled to room temperature, and then gradually poured into ice water. Sodium hydroxide was added to the solution. Afterwards, the precipitate was filtered out, and then purified with a silica gel column (mobile phase: petroleum ether and dichloromethane) to obtain a white solid B 1 (3.4 g, 65.1%), MS (EI, m / z) 506.9.

[0132] ②Compound B 1 (3.4 g, 6.7 mmol) and trimethyl-(6-octylthienoselenophene)tin (11.1 g, 24.0 mmol) were dissolved in 100 mL of anhydrous toluene. Ar 2 Under protection, the Pd(PPh 3 ) 4 (0.8g, 0.69mmol) was added to the reaction solution, and stirred at reflux at...

Embodiment 2

[0140] A kind of preparation method of acceptor molecule NH-CN based on benzimide, as attached figure 2 The synthetic route is shown as:

[0141] S10. Compound A 2 Synthesis of aldehyde compound NH based on benzimide as starting material.

[0142] ①Compound A 2 (4.1g, 6.3mmol) was dissolved in concentrated sulfuric acid / fuming nitric acid (30mL / 75mL), refluxed at 90°C for 15 hours, then cooled to room temperature, and then gradually poured into ice water. Sodium hydroxide was added to the solution. Afterwards, the precipitate was filtered out, and then purified with a silica gel column (mobile phase: petroleum ether and dichloromethane) to obtain compound B as a white solid 2 (3.4 g, 4.6 mmol, 73.0%), MS (EI, m / z) 736.1.

[0143] ②Compound B 2 (3.4 g, 4.6 mmol) and trimethyl-(6-octylthienothiophene)tin (10.5 g, 22.7 mmol) were dissolved in 100 mL of anhydrous toluene. Ar 2 Under protection, the Pd(PPh 3 ) 4 (0.8g, 0.69mmol) was added to the reaction solution, and ...

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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 benzoimide. A preparation method comprises the steps: taking a unit containing benzoimide or dibenzoimide as an electron donating unit D, taking a group rich in cyano groups and ketone groups as an electron withdrawing unit A, and simultaneously connecting the electron withdrawing unit A to two ends of the central electron donating unit D to form a benzoimide polycyclic receptor micromolecule with an A-D-A conjugated structure. The benzoimide-based acceptor materialdisclosed by the invention has relatively strong light absorption in an ultraviolet-visible light region (600-1000 nm) and a narrow optical band gap (1.07 eV), has more matched energy level and highercarrier migration rate compared with an existing wide band gap donor material, and is easy to dissolve in a common organic solvent. When the material is applied to organic solar cells, high short-circuit current (12.75 mA / cm<2>) and energy conversion efficiency (5.85%) can be achieved, and the material has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic solar cells, and in particular relates to a benzimide-based acceptor material and a preparation method thereof, as well as 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 c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D517/22H01L51/42H01L51/46
CPCC07D517/22H10K85/626H10K85/657H10K30/00Y02E10/549
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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