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CN-121974929-A - Lipoic acid in-situ crosslinking receptor material for organic solar cell and preparation method and application thereof

CN121974929ACN 121974929 ACN121974929 ACN 121974929ACN-121974929-A

Abstract

The invention provides an organic solar cell receptor material containing a octanoic acid group, a preparation method and application thereof. The chemical structural formula of the acceptor material is as follows: Wherein AK is selected from one of saturated alkyl chain, ether chain or siloxane chain with 1-20 carbon atoms, X, Y is independently selected from H, I, F or Cl. According to the invention, the cross-linking group lipoic acid is introduced into the organic solar cell receptor material for the first time, and the disulfide bonds of the material can realize dynamic ring opening under the conditions of ultraviolet irradiation and heating, so that the material can improve the microcosmic appearance of an active layer film in an organic solar cell device, the stability of the photovoltaic device is improved, the mechanical property of the device is enhanced, and the balance problem between the mechanical durability and the photoelectric property of the photovoltaic device is improved.

Inventors

  • CHEN ZHENYU
  • HU YONGCHAO
  • QIN SHANSHAN
  • SHI JINRONG

Assignees

  • 福建师范大学

Dates

Publication Date
20260505
Application Date
20260120

Claims (10)

  1. 1. An in situ crosslinking acceptor material, characterized by the following chemical structural formula: , Wherein AK is selected from one of saturated alkyl chain, ether chain or siloxane chain with 1-20 carbon atoms, X, Y is independently selected from hydrogen atom, I, F or Cl.
  2. 2. A method of preparing an in situ cross-linked acceptor material according to claim 1 comprising the steps of: 1) Dissolving conjugated organic molecules and zinc powder in an organic solvent, heating to 110 ℃ under the protection of inert gas, reacting for 60-90 min ℃, filtering to remove the zinc powder after the reaction is finished, adding methylene dichloride, uniformly mixing, extracting, and drying to obtain a crude product; 2) Dissolving the crude product obtained in the step 1) and 4, 4-dihydroxybenzil in an organic solvent, reacting at room temperature under the protection of inert gas for 12h, and extracting, drying, separating and purifying by column chromatography after the reaction is finished to obtain a compound with a quinoxaline center core; 3) Under the protection of inert gas, dissolving the compound with the quinoxaline center core prepared in the step 2) in an organic solvent, then dropwise adding lithium diisopropylamide at the temperature of minus 78 ℃ and reacting for 30min, then dropwise adding N, N-dimethylformamide, reacting for 30-90 min at room temperature, and extracting, drying, separating and purifying by column chromatography after the reaction is finished to obtain a dialdehyde compound; 4) Dissolving the dialdehyde compound obtained in the step 3) with 4-dimethylaminopyridine and thiooctanoic acid in an organic solvent, reacting at normal temperature under the protection of inert gas for 5-10 min, dropwise adding 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide dissolved in the organic solvent, reacting at normal temperature for 12: 12 h, extracting, drying, and separating and purifying by column chromatography after the reaction is finished to obtain a compound containing a sulfuric octanoic acid group; 5) Dissolving the compound containing the octanoic acid group obtained in the step 4) and halogenated cyano indenone in an organic solvent, dripping a catalyst under the protection of inert gas, reacting at room temperature for 12h, pouring the reaction system into methanol after the reaction is finished, filtering to obtain a crude product, and separating and purifying by column chromatography to obtain a final product.
  3. 3. The process of claim 2, wherein the molar ratio of conjugated organic molecules to zinc powder used in step 1) is 1 (4-5), and the conjugated organic molecules have the chemical structural formula Wherein AK is selected from one of saturated alkyl, ether chain or siloxane chain with 1-20 carbon atoms.
  4. 4. The process according to claim 2, wherein the molar ratio of the crude product used in step 2) to 4, 4-dihydroxybenzil is 1:2.
  5. 5. The process according to claim 2, wherein the molar ratio of the compound having a quinoxaline central core used in step 3) to lithium diisopropylamide, N-dimethylformamide is1 (4-5): 100-120.
  6. 6. The process according to claim 2, wherein the molar ratio of the dialdehyde compound, 4-dimethylaminopyridine, lipoic acid to 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide used in step 4) is 1:5:5:5.
  7. 7. The process according to claim 2, wherein the molar ratio of the compound having a octanoic acid group, the halocyanoindanone and the catalyst used in step 5) is 1 (3-4): 0.1-0.3, and the catalyst is pyridine.
  8. 8. The preparation method according to claim 2, wherein the organic solvent used in the operation is any one of chloroform, tetrahydrofuran and acetic acid.
  9. 9. Use of the in situ crosslinking acceptor material of claim 1 for the preparation of an organic solar cell.
  10. 10. Use according to claim 9, characterized in that the in-situ cross-linked acceptor material is used as an active layer acceptor material, mixed with a donor material for the preparation of photoactive layers of organic solar cells.

Description

Lipoic acid in-situ crosslinking receptor material for organic solar cell and preparation method and application thereof Technical Field The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an organic solar cell receptor material containing a octanoic acid group, a preparation method and application thereof. Background Along with the serious and serious problems of environmental pollution, exhaustion of fossil energy and the like, the search for developing a novel green sustainable development energy becomes an important issue for the development of human society. In recent years, solar energy among many renewable energy sources has been receiving attention from society because of its advantages of green, easy availability and inexhaustible use. However, the conventional silicon-based solar cell has high cost, poor cell flexibility and complex preparation process. Therefore, developing a flexible, low-cost, green solar cell is of great importance. Organic solar cells (Organic Solar Cells, OSCs) are widely used in the fields of wearable equipment, photovoltaic building integration and the like due to the advantages of flexibility, low cost, expandable manufacturing, simple manufacturing process and the like. With the high-speed development of the field of organic solar cells and the continuous research on photoelectric conversion mechanisms, the photoelectric conversion efficiency (Power Conversion Efficiency, PCE) of the organic solar cells has broken through 20% at present, and has great application potential. However, the organic solar cell still has limited industrialization due to the problem of balancing thermal stability, mechanical durability and photoelectric properties. At present, two main modes for improving the thermal stability and the flexibility of an organic solar cell are provided, namely, a functional group is introduced to construct non-covalent interaction among molecules, a hydrogen bond is utilized to realize chemical crosslinking among the donor/acceptors, and a crosslinking group is introduced to a chemical skeleton of the modification of the donor/acceptors to realize in-situ crosslinking among the molecules. The lipoic acid has dynamic disulfide bond, can be dynamically opened under the conditions of heating and ultraviolet irradiation, and in addition, research shows that the disulfide bond can be healed independently at room temperature, so that the lipoic acid has a profound application prospect in a scalable organic solar cell device. The cross-linking group lipoic acid is applied to the organic solar cell small molecule acceptor material for the first time, and the cross-linking group lipoic acid shows excellent device performance in a photovoltaic device. Disclosure of Invention The invention aims to provide a lipoic acid in-situ crosslinking acceptor material for an organic solar cell, a preparation method and application thereof, wherein the material connects a crosslinking group lipoic acid into acceptor small molecules for the first time, disulfide bonds in lipoic acid can be broken by ultraviolet irradiation or heating so as to generate in-situ crosslinking, and further the stability and flexibility of the photoelectric functional device can be improved. In order to achieve the above purpose, the invention adopts the following technical scheme: One of the purposes of the present invention is to protect an in situ crosslinking acceptor material, the chemical structural formula of which is as follows: , Wherein AK is selected from one of saturated alkyl chain, ether chain or siloxane chain with 1-20 carbon atoms, X, Y is independently selected from hydrogen atom, I, F or Cl. Preferably, AK in the chemical formula is specifically one of n-undecane (-C 11H24), 2-ethylhexyl (-C 8H16) or 2-butyloctyl (-C 11H24). The second purpose of the invention is to protect the preparation method of the in-situ crosslinking acceptor material, which comprises the following reaction flow: ; the preparation method comprises the following steps: 1) Dissolving conjugated organic molecules (a) and zinc powder in an organic solvent, heating to 110 ℃ under the protection of inert gas, reacting for 60-90 min ℃, filtering to remove the zinc powder after the reaction is finished, adding methylene dichloride, mixing uniformly, extracting an organic phase with distilled water for 3 times, then merging the organic phases, adding a drying agent for drying, and performing reduced pressure distillation to spin-dry the organic phase to obtain a crude product; 2) Dissolving the crude product obtained in the step 1) and 4, 4-dihydroxybenzil (b) in an organic solvent, reacting at room temperature under the protection of inert gas for 12 h times, adding distilled water to extract an organic phase for 3 times after the reaction is finished, then merging the organic phases, adding a drying agent to dry, performing reduced pressure distillation to spin-dry th