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Hole transport material with interface passivation and hole transport functions as well as preparation method and application of hole transport material

A hole-transporting material and hole-transporting technology, applied in the field of low-cost dual-functional hole-transporting materials, can solve the problems of long-term stability of devices, limiting device performance, poor charge transport, etc., and achieve good photophysical properties and photovoltaic high performance, reduced preparation cost, low cost effect

Active Publication Date: 2021-07-09
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Currently, CsPbIBr 2 The device structure mainly adopts FTO / electron transport layer / CsPbIBr spin-coated void transport layer 2 / Hole transport layer / Metal or FTO without hole transport layer / Electron transport layer / CsPbIBr 2 / carbon structure, the hole transport material in the former device is mainly high-cost Spiro-OMeTAD, and it needs to add hygroscopic or corrosive additives (bistrifluoromethanesulfonylimide lithium or 4-tert-butylpyridine), the latter With the use of cheap carbon as a synergistic replacement for hole transport and electrodes, however, its poor charge transport and mismatched energy levels greatly limit the improvement of device performance.
In addition, CsPbIBr 2 Defects in the film itself also have a great impact on the long-term stability of the device

Method used

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  • Hole transport material with interface passivation and hole transport functions as well as preparation method and application of hole transport material
  • Hole transport material with interface passivation and hole transport functions as well as preparation method and application of hole transport material
  • Hole transport material with interface passivation and hole transport functions as well as preparation method and application of hole transport material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The synthetic route of the hole transport material SP-HTL1 is as follows:

[0050]

[0051] 1,4-Dibromo-2,5-difluorobenzene (compound 1, 2.7 g, 10 mmol), compound 2 (4.7 g, 20.5 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), P(o-tol) 3 (0.61 g, 2.0 mmol) and t-BuONa (0.22 g, 2.3 mmol) were placed in a 100 mL single-necked flask, vacuumed and filled with nitrogen for 3 to 4 times, and 30 mL of anhydrous toluene was added under nitrogen protection. Heat the reaction flask in an oil bath to 110 o C was stirred overnight. After the mixture was cooled to room temperature, the mixed liquid was poured into deionized water, and the aqueous phase was extracted with 3×30 mL of dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was spun off under reduced pressure. The compound SP-HTL1 was obtained by silica gel column chromatography (developing solvent: ethyl acetate / petroleum ether, volume ratio 1:5~1:4), 4.50 g o...

Embodiment 2

[0053] The synthesis route of the hole transport material SP-HTL2 is as follows:

[0054]

[0055] 1,4-Dibromobenzene (Compound 3, 2.1 g, 9 mmol), Compound 4 (4.7 g, 18.9 mmol), Pd 2 (dba) 3 (0.44 g, 0.48 mmol), P(o-tol) 3 (0.58 g, 1.9 mmol) and t-BuONa (0.21 g, 2.2 mmol) were placed in a 100 mL single-necked flask, vacuumed and filled with nitrogen for 3 to 4 times, and 30 mL of anhydrous toluene was added under nitrogen protection. Heat the reaction flask in an oil bath to 110 o C was stirred overnight. After the mixture was cooled to room temperature, the mixed liquid was poured into deionized water, and the aqueous phase was extracted with 3×30 mL of dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was spun off under reduced pressure. Compound SP-HTL2 was obtained by silica gel column chromatography (developing solvent: ethyl acetate / petroleum ether, volume ratio 1:5~1:4), white solid 3.53 g, yield...

Embodiment 3

[0057] The synthetic route of the hole transport material SP-HTL3 is as follows:

[0058]

[0059] 1,4-dibromo-2,5-dichlorobenzene (compound 5, 2.4g, 8 mmol), compound 6 (4.7 g, 17.0 mmol), Pd 2 (dba) 3 (0.38 g, 0.42 mmol), P(o-tol) 3 (0.52 g, 1.7 mmol) and t-BuONa (0.17 g, 1.8 mmol) were placed in a 100 mL single-necked flask, vacuumed and filled with nitrogen for 3 to 4 times, and 30 mL of anhydrous toluene was added under nitrogen protection. Heat the reaction flask in an oil bath to 110 o C was stirred overnight. After the mixture was cooled to room temperature, the mixed liquid was poured into deionized water, and the aqueous phase was extracted with 3×30 mL of dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was spun off under reduced pressure. The compound SP-HTL3 was obtained by silica gel column chromatography (developing solvent: ethyl acetate / petroleum ether, volume ratio 1:5~1:4), 4.30 g of...

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Abstract

The invention discloses a hole transport material with interface passivation and hole transport functions as well as a preparation method and application thereof. The molecular structural formula of the hole transport material SP-HTL is shown in the specification, wherein X and Y are H, Cl, F, or other multi-element fused ring units with electron donating capability. In addition, the series of hole transport materials SP-HTL designed and synthesized by the invention have relatively deep HOMO energy level, relatively narrow optical absorption and relatively strong interface passivation performance. Besides, the series of hole transport materials SP-HTL designed and synthesized in the patent of the invention have relatively low required concentration in a device preparation process, and can obtain better photoelectric conversion efficiency than Spiro-OMeTAD under the condition of not needing an additive.

Description

technical field [0001] The invention belongs to the field of organic synthesis and application of inorganic perovskite batteries, and in particular relates to a class of low-cost dual-functional hole transport material with both interface passivation and hole transport, its preparation method and its application. Background technique [0002] Organic-inorganic Hybrid Halide-lead Perovekite Solar Cells (Organic-inorganic Hybrid Halide-leadPerovekite Solar Cells, OiHl-PSCs) have good carrier transport properties, high film molar absorptivity, long excitation Many advantages such as sub-diffusion distance, small exciton binding energy and tunable optical bandgap have attracted the attention of researchers in industry and academia. What is even more interesting is that the efficiency of OiHl-PSCs cells has rapidly increased from 3.81% in 2009 to the current level through the efforts of researchers in perovskite composition adjustment, morphology improvement, interface optimizati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/92C07C213/08C07C213/10C07C323/37C07C319/20C07C319/28H01L51/54H01L51/50H01L51/52H01L51/56
CPCC07C217/92C07C213/08C07C213/10C07C323/37C07C319/20C07C319/28H10K50/15H10K50/84H10K71/00
Inventor 高跃岳何盛华尚陆文黄军意谭付瑞岳根田
Owner HENAN UNIVERSITY
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