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Thiophene-carbazole core four-arm hole transport material as well as preparation method and application thereof

A technology of hole transport material and carbazole core, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., and can solve the problem of unfavorable stability of battery devices, decreased stability of battery devices, and easy damage to perovskite layers, etc. problems, to achieve the effects of inhibiting interface electron recombination, mild reaction conditions, and high photoelectric conversion efficiency

Active Publication Date: 2020-05-15
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The hole mobility of such amorphous hole-transporting layer materials is generally low, among which Spiro-OMeTAD and PTAA require bis(trifluoromethylsulfonyl)lithium (Li-TFSI) and 4-tert-butylpyridine (TBP ) as p-type doping, such doping molecules will have a negative impact on the stability of the battery device; while PEDOT:PSS does not require doping, but the polyelectrolyte has strong hygroscopicity and is easy to damage the perovskite layer. On the other hand, the acidity of PEDOT:PSS will cause corrosion to the ITO glass, and it is easy to absorb moisture, resulting in a decrease in the stability of the battery device.

Method used

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  • Thiophene-carbazole core four-arm hole transport material as well as preparation method and application thereof
  • Thiophene-carbazole core four-arm hole transport material as well as preparation method and application thereof
  • Thiophene-carbazole core four-arm hole transport material as well as preparation method and application thereof

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Experimental program
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Embodiment

[0038] Example: Synthesis of thiophene-carbazole core four-arm hole transport material

[0039] Synthesis of Intermediate 5:

[0040]

[0041] Weigh p-iodoanisole (5.1 g, 21.78 mmol), p-bromoaniline (1.5 g, 8.71 mmol), cuprous chloride (165 mg, 1.66 mmol), potassium hydroxide (3.9 g, 69.51 mmol) and 1, 10-Phenanthroline (315 mg, 1.66 mmol) was placed in a 100 ml two-necked bottle, and the nitrogen gas was replaced by vacuum three times. Add 30 mL of toluene into the two-neck flask, stir and heat under reflux for about 10 hours. After the reaction was completed, it was extracted with dichloromethane, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography, using a mixed solvent with a volume ratio of dichloromethane:petroleum ether=1:10 as eluent to obtain the target compound, product 5 was a white solid, and the yield was 80%.

[0042] Synthesis of Intermediate 6:...

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Abstract

The invention discloses a thiophene-carbazole core four-arm hole transport material as well as a preparation method and application thereof; thiophene-carbazole is taken as a core, so that the HOMO energy level and LUMO energy level of the material are remarkably higher than those of mixed halogen perovskite, electrons can be prevented from jumping to a hole transport layer from a perovskite layer, and an interface electron recombination phenomenon is effectively inhibited. The preparation method comprises the following steps: carrying out a coupling reaction on p-iodoanisole and p-bromoaniline to generate an intermediate (5); carrying out substitution reaction on the intermediate (5) and bis(pinacolato)diboron to generate an intermediate (6); carrying out coupling reaction on the intermediate (6) and 2,3-dibromothiophene to generate an intermediate (7); carrying out bromination reaction on the intermediate (7) to generate an intermediate (8); carrying out coupling reaction on the intermediate (6) and 3,6-dibromocarbazole to generate an intermediate (9); and carrying out coupling reaction on the intermediate (9) and the intermediate (8) to generate a final product CZ-1. When the hole transport material provided by the invention is used for a perovskite solar cell, a cell device has relatively high photoelectric conversion efficiency.

Description

technical field [0001] The invention belongs to the technical field of perovskite solar cells, and relates to a doped hole transport material, in particular to a thiophene-carbazole core four-arm hole transport material and its preparation method and application. Background technique [0002] With the continuous development of the global economy and society, the demand for energy by human society is increasing, and traditional fossil energy is becoming more and more difficult to meet the needs of economic and social development. In addition, the extensive use of traditional fossil energy will cause serious damage to the natural environment and aggravate the extent of the greenhouse effect. Therefore, seeking new renewable and pollution-free energy has become the first problem that human society must face. Due to its renewable and non-polluting advantages, solar energy is inexhaustible, unlike traditional fossil energy, which has a very long formation cycle. Therefore, how ...

Claims

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Application Information

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IPC IPC(8): C07D409/04H01L51/46H01L51/42
CPCC07D409/04H10K85/655H10K85/631H10K30/10H10K85/6572Y02E10/549
Inventor 郑菲陈小燕宋鑫瑶徐晓楠包小春
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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