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Non-fused electron acceptor material, preparation method and organic solar cell formed by non-fused electron acceptor material

An electron acceptor material, solar cell technology, applied in the fields of organic chemistry, electro-solid devices, semiconductor/solid-state device manufacturing, etc. Increase the cost of material synthesis and other issues to achieve the effect of low synthesis cost, suitable energy level and wide absorption range

Pending Publication Date: 2019-03-08
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(Nat.Mater.2018,17,119; Nat.Rev.Mater.2018,3,18003; Nat.Photon.2018,12,131.) However, the synthesis process of condensed ring molecules is cumbersome, which not only increases the cost of material synthesis, but is not conducive to Promoting its industrialization process has also caused certain obstacles to the in-depth study of the structure-activity relationship of non-fullerene acceptors

Method used

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  • Non-fused electron acceptor material, preparation method and organic solar cell formed by non-fused electron acceptor material
  • Non-fused electron acceptor material, preparation method and organic solar cell formed by non-fused electron acceptor material
  • Non-fused electron acceptor material, preparation method and organic solar cell formed by non-fused electron acceptor material

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Experimental program
Comparison scheme
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Embodiment 1

[0038] Using 1,4-dibromo-2,5-dihydroxybenzene as the initial raw material to synthesize PTIC, the reaction equation is:

[0039]

[0040] Among them, intermediate 1 was synthesized by the method reported in the literature Angewandte Chemie, International Edition, 2016, 55(2), 703-707; The synthetic steps of intermediate 2 and final product 3 are:

[0041] Under argon protection, intermediate 1 (395mg, 0.55mmol), 3-hexylthiophenecarbaldehyde (320mg, 1.64mmol), tricyclohexylphosphine fluoroborate (8.1mg, 0.022mmol), trimethylacetic acid (17mg , 0.17mmol), potassium carbonate (114mg, 0.83mmol), and toluene (20mL) were placed in a Schlenk vacuum-sealed bottle. After liquid nitrogen freezing, three cycles of evacuation and argon followed by addition of Pd(OAc) 2 (2.5mg, 0.011mmol), and then frozen for three times. Heat to reflux at 80°C for 24 hours. After the reaction, the reaction solution was extracted with dichloromethane, the organic phase was collected, washed with wat...

Embodiment 2

[0044] After the transparent conductive glass with strip-shaped ITO (cathode) etched on the surface is cleaned with cleaning agent, deionized water, acetone and isopropanol by ultrasonic oscillation, it is dried and treated with oxygen plasma for 15 minutes; Zinc oxide was spin-coated on the surface at a speed of 3000r / min, and dried at 150°C for 10 minutes; then, a mixed solution of PBDB-TF and PTIC was spin-coated on it at a speed of 3000r / min, and the total concentration of the solution was 15mg / mL. The solvent is chlorobenzene, the weight ratio of PBDB-TF and PTIC is 1:1.2, and the spin coating time is 40 seconds to obtain a blend film (active layer) of PBDB-TF and PTIC with a thickness of 100nm; annealing treatment at 120°C 10 minutes; then a layer of MoO was spin-coated on the active layer 3 , the rotating speed is 3000r / min, the concentration of the solution is 2mg / ml; finally, when the pressure is lower than 5×10 -4 A layer of Ag with a thickness of 100nm was evaporat...

Embodiment 3

[0048] Using 1,4-dibromo-2,5-dihydroxybenzene as the initial raw material to synthesize PTICH_H, the reaction equation is:

[0049]

[0050] Among them, intermediate 1 was synthesized by the method reported in the literature Angewandte Chemie, International Edition, 2016, 55(2), 703-707; The synthetic steps of intermediate 5 and target product 6 are:

[0051] 1 (395mg, 0.55mmol), K 2 CO 3 (114mg, 0.83mmol), palladium acetate (2.5mg, 0.011mmol), PCy 3 ·HBF 4 (8.1mg, 0.022mmol) and trimethylacetic acid (17mg, 0.17mmol) were added to a 50mL two-neck round bottom flask. Flasks connected N 2 Take three breaths. then in N 2 2-thiophenecarbaldehyde (185 mg, 1.65 mmol) and toluene (15 mL) were added under protection. Reaction solution in N 2 Heat to reflux at 80° C. for 16 hours under atmosphere. After the reaction, cool to room temperature, add saturated saline, and extract three times with dichloromethane, combine the organic layers, dry using anhydrous magnesium sulfate ...

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Abstract

The invention discloses a non-fused electron acceptor material, a preparation method and an organic solar cell formed by the non-fused electron acceptor material. The non-fused electron acceptor material comprises a lining, a negative pole, an electron transfer layer, an active layer, a positive pole modification layer and a positive pole, wherein the active layer is a blended membrane of a polymer donor and a novel receptor. The prepared organic solar cell has very high VOC (open-circuit voltage) (0.9-1.1V) and widened spectral response range (300-850nm), and the highest PCE (energy conversion efficiency) can exceed 10.00%.

Description

technical field [0001] The invention belongs to the field of energy materials, in particular to a non-condensed electron acceptor material and its application. Background technique [0002] Organic photovoltaic materials based on non-fullerene acceptors have developed rapidly in recent years. Among them, the highest efficiency of binary devices has exceeded 14% (Adv. Mater. 2018, 1800868), and the highest efficiency of stacked devices has exceeded 17% (ScienceDOI: 10.1126 / science.aat2612). However, most of the current high-efficiency non-fullerene acceptors belong to the class of fused ring materials. This can not only maintain the planarity of the material to ensure the effective progress of the intramolecular charge transfer process (ICT), but also use the side groups extended from the sp3 carbon atoms on the fused ring molecule to effectively avoid excessive accumulation of molecules to control the phase morphology. . (Nat.Mater.2018,17,119; Nat.Rev.Mater.2018,3,18003;...

Claims

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Application Information

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IPC IPC(8): C07D333/24C07D333/78H01L51/46
CPCC07D333/24C07D333/78H10K85/626H10K85/655H10K85/6576H10K30/00Y02E10/549
Inventor 李昌治余志鹏刘志玺秦冉陈红征
Owner ZHEJIANG UNIV