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Isoindigo-based narrow band gap donor material and preparation method thereof

A narrow band gap and donor technology, applied in the field of organic solar cell materials, can solve the problems of low solubility of poly-3-hexylthiophene, unfavorable processing of organic solar cells, etc., and achieve excellent short-circuit current and good solubility.

Inactive Publication Date: 2016-09-21
NINGBO XIAYUAN TECH
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0006] However, the commonly used donor material poly-3-hexylthiophene reported in the prior art has low solubility, which is not conducive to the processing of organic solar cells

Method used

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  • Isoindigo-based narrow band gap donor material and preparation method thereof
  • Isoindigo-based narrow band gap donor material and preparation method thereof
  • Isoindigo-based narrow band gap donor material and preparation method thereof

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preparation example Construction

[0030] Correspondingly, the present invention also provides a preparation method of a narrow bandgap donor material based on isoindigo, comprising the following steps: step a1) under the protection of nitrogen, the first compound shown in formula 3, the second compound shown in formula 4 Mix the two compounds, tetrakis(triphenylphosphine)palladium and toluene, heat to 80-120°C and stir for 20-30 hours, cool,

[0031]

[0032] Step a2) filtering and drying the organic phase obtained in step a1 to obtain a narrow band gap donor material.

[0033] As a preferred version, the molar ratio of the first compound, the second compound and tetrakis (triphenylphosphine) palladium is preferably 85-90:40-45:4-6, more preferably 86-90:40-44: 5~6. In step a1, the heating temperature is preferably 100°C, and the stirring time is preferably 24 hours.

[0034] As a preferred solution, the step a2 is: filter the organic phase obtained in the step a1 through diatomaceous earth, dry the filtr...

Embodiment 1

[0056] Embodiment 1: Preparation of narrow bandgap donor material based on isoindigo

[0057] Step 1): Preparation of the third compound

[0058] To the reaction vessel was added 5-hexyl-2,2-dithiophene (1.17 g, 4.7 mmol), followed by 20 mL of anhydrous diethyl ether. The reaction system was placed in liquid nitrogen and cooled to -78°C. At -78°C, n-butyl lithium in n-hexane (2.5 mol / L, 2.8 mL, 6.9 mmol) was added to the reaction system. Then, the reaction system was stirred at -78°C for 1 hour. Add 5 mL of a diethyl ether solution of tributyltin chloride (1.4 g, 6.9 mmol) into the reaction system. Subsequently, the reaction system was stirred at room temperature for 12 hours. After the reaction, the organic phase was repeatedly washed with deionized water, dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum rotary evaporation to obtain the third compound, a total of 1.9 g, with a yield of 99%.

[0059] 1 H NMR (CDCl 3 , 300MHz, 298K) δ7.22(d, ...

Embodiment 2

[0075] Example 2: Preparation of organic solar cells and device performance measurement

[0076] Poly-3-hexylthiophene is a commonly used donor material in organic solar cells, and it is used as a reference material in device performance testing. The isoindigo-based narrow bandgap material and poly-3-hexylthiophene prepared in Example 1 are respectively used as donor materials, and [6,6]-phenyl-carbon 61-butyric acid methyl ester (PC61BM) is used as acceptor materials, Group A and Group B organic solar cells were prepared.

[0077] Place an ITO (indium tin oxide) conductive glass sheet in a glove box, and spin-coat an active layer film with a thickness of 100 nm. In the active layer, the blending mass ratio of the donor material and PC61BM is 1:1, and chloroform is selected as the solvent. The ITO glass sheet with the active layer spin-coated was transferred to an evaporation chamber, and a layer of Al with a thickness of 60 nm was evaporated to prepare an organic solar cell...

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Abstract

The invention discloses an isoindigo-based narrow band gap donor material and a preparation method thereof. The method comprises the following steps: 1, mixing a first compound, a second compound, tetrakis(triphenylphosphine)palladium and toluene under the protection of nitrogen, heating the obtained mixture to 80-120DEG C, stirring the heated mixture for 20-30h, and cooling the stirred mixture; and 2, filtering an organic phase obtained in step 1, and drying the filtered organic phase to obtain the narrow band gap donor material. Compared with narrow band gap donor materials in the prior art, the narrow band gap donor material prepared in the invention contains isoindigo and thiophene units, and has excellent short circuit current, photoelectric conversion efficiency and external quantum efficiency when applied to organic solar batteries. The narrow band gap donor material prepared in the invention is a low molecular material, has good dissolvability, can be easily dissolved in organic solvents and coated, and is suitable for processing technologies of the organic solar batteries.

Description

technical field [0001] The invention relates to the technical field of organic solar cell materials, in particular to an isoindigo-based narrow bandgap donor material and a preparation method thereof. Background technique [0002] With the development of industry, energy consumption has increased sharply, and solar cells use sunlight as an infinite energy source, which has great application value. Most of the solar cells currently used are monocrystalline silicon and polycrystalline silicon type inorganic solar cells, however, inorganic silicon solar cells have the disadvantages of complicated manufacturing process and high cost. [0003] The active layer of organic solar cells adopts organic optoelectronic materials that are light, flexible, cheap, designable and synthetic, and can be processed by solution. It is expected to greatly reduce the cost of solar power generation, and it is also easy to realize large-area and flexible devices. However, compared with inorganic so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10H01L51/46
CPCC07F7/0816H10K85/40Y02E10/549
Inventor 魏亮
Owner NINGBO XIAYUAN TECH
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