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Electron-deficient heterocyclic core small-molecule electron donor material as well as preparation and application thereof

An electron donor material and core small molecule technology, applied in the field of solar cells, can solve problems such as scarcity of optimizeable sites and modifiable units, single structure of oligothiophene, and few optimization strategies, and achieve excellent photoelectric conversion efficiency and synthetic route Less, avoid complex effects

Active Publication Date: 2022-08-09
CHONGQING INST OF GREEN & INTELLIGENT TECH CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the single structure of oligothiophene, the scarcity of optimized sites and modifiable units, its optimization strategies in structure design are rare, which restricts its development in small molecule electron donor materials.

Method used

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  • Electron-deficient heterocyclic core small-molecule electron donor material as well as preparation and application thereof
  • Electron-deficient heterocyclic core small-molecule electron donor material as well as preparation and application thereof
  • Electron-deficient heterocyclic core small-molecule electron donor material as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] like figure 1 As shown, the preparation process of the electron-deficient heterocyclic core small molecule electron donor material in this embodiment is as follows:

[0083] 1. Synthesis of compound 2

[0084] Compound 1 (1.0 equiv. purchased from Anaiji) and octylthiophene tin reagent (2.4 equiv. purchased from Gea) were dissolved in 50 ml of anhydrous toluene, and then Pd(PPh3)4 (tetrakistriphenylphosphine palladium) 150 mg. The reaction was stirred at 130°C for 48 hours. Then the solvent was removed under reduced pressure, separated by silica gel column chromatography, the eluent was chloroform / petroleum ether (by volume, chloroform:petroleum ether=1:6), the product (compound 2) was a pale yellow oil (the yield was the theoretical yield) 65%).

[0085] Characterization data for compound 2: 1H NMR (400 MHz, Acetone, δppm): 7.72 (d, J=5.2 Hz, 1H), 7.39 (d, J=4.8 Hz, 1H), 7.20 (d, J=5.2 Hz, 1H) ),7.04(d,J=5.2Hz,1H),3.97(s,3H),3.18(t,J=7.6Hz,2H),2.85-2.81(m,3H),1.73...

Embodiment 2

[0095] like figure 1 As shown, the preparation process of the electron-deficient heterocyclic core small molecule electron donor material in this embodiment is as follows:

[0096] 1. Synthesis of compound 2

[0097] Dihalogenated isothiadiazoles (1.0 equiv. purchased from Anaiji) and octylthiophene tin reagent (2.4 equiv. purchased from Gea) were dissolved in 50 ml of anhydrous toluene, and then Pd(PPh3)4 (tetratriphenylene) was added phosphine palladium) 150 mg. The reaction was stirred at 130°C for 48 hours. Then the solvent was removed under reduced pressure, separated by silica gel column chromatography, the eluent was chloroform / petroleum ether (by volume, chloroform:petroleum ether=1:6), and the product (compound 2) was a pale yellow oil (the yield was the theoretical yield 40%).

[0098] Characterization data of compound 2: 1H NMR (400MHz, CDCl3, δppm): 7.45 (d, J=4.8Hz, 1H), 7.32 (d, J=5.2Hz, 1H), 7.03 (d, J=5.2Hz, 1H) ),6.99(d,J=4.8Hz,1H),3.23(t,J=7.6Hz,2H),2.91...

Embodiment 3

[0108] The electron-deficient heterocyclic core small molecule electron donor material (ie figure 1 3N6T) as shown in the preparation of an all-small-molecule organic solar cell, the specific preparation process is as follows:

[0109] The substrate composed of transparent glass and transparent conductive electrode ITO was ultrasonically cleaned with cleaning solution, deionized water, acetone and isopropanol respectively, and dried with nitrogen after cleaning; the substrate was placed in an ozone cleaning machine for 15min. , the hole transport layer material PEDOT:PSS was spin-coated in air (4000rpm, 20s, film thickness 30nm), followed by thermal annealing in air (120°C, 10min), and then the samples were transferred into a nitrogen-filled glove box , the active layer (3N6T:BTP-eC9-4F=2:1, 40mg / ml, active layer thickness: ≈ 200nm) was prepared by spin coating on the PEDOT:PSS hole transport layer, and the obtained active layer thin film Solvent annealing treatment (CF, 30 s...

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Abstract

The invention belongs to the technical field of solar cells, and particularly discloses an electron-deficient heterocyclic core micromolecule electron donor material and preparation and application thereof. The micromolecular electron donor material with an A-D-A '-D-A type skeleton structure is prepared by taking a brand-new electron-deficient heterocyclic ring unit which is never applied to an organic solar cell as a core unit, and the molecular structure of the micromolecular electron donor material is shown as a formula (I). The small-molecule electron donor material has good solubility, stability, photoelectric property and solution processability, and the full-small-molecule organic solar cell prepared from the small-molecule electron donor material has excellent photoelectric conversion efficiency. The invention provides a brand-new and simple synthetic route for the structural design of a small-molecule electron donor material, and has huge application potential and value in organic solar cells and related photovoltaic fields.

Description

technical field [0001] The invention relates to the technical field of solar cells, in particular to an electron-deficient heterocyclic core small molecule electron donor material and its preparation and application. Background technique [0002] As a kind of flexible and printable solar cells, organic solar cells are composed of organic semiconductor materials to form the core part of solar cells. They have the advantages of wide source of raw materials, good flexibility, solution processing, and printability. In recent years, organic solar cells have become one of the research hotspots in the industry. In the past two years, organic solar cells have developed rapidly. The photoelectric conversion efficiency of all-small-molecule organic photovoltaic devices using non-fullerene as acceptor material has exceeded 16%. However, the price of non-fullerene electron acceptor materials is higher than that of fullerenes. Expensive and non-Fuller-system organic solar cells are sens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14H01L51/46H01L51/42
CPCC07D417/14H10K85/656H10K85/6565H10K85/655H10K85/654H10K30/00Y02E10/549C07D495/04C07D409/14H10K30/30
Inventor 陈骞骞胡定琴陆仕荣段泰男
Owner CHONGQING INST OF GREEN & INTELLIGENT TECH CHINESE ACADEMY OF SCI
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