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Thiophene-bridged pyrenetetramine hole-transport material and application of same to perovskite solar cell

A hole-transporting material and hole-transporting layer technology, used in circuits, photovoltaic power generation, electrical components, etc., can solve the problems of high price, many synthesis steps, and difficult purification, and achieve improved performance, convenient purification, and good holes. The effect of transmission performance

Active Publication Date: 2018-09-04
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the hole transport material spiro-OMeTAD has shown good performance in perovskite solar cells, its disadvantages are many synthesis steps, difficult purification, and high price.

Method used

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  • Thiophene-bridged pyrenetetramine hole-transport material and application of same to perovskite solar cell
  • Thiophene-bridged pyrenetetramine hole-transport material and application of same to perovskite solar cell
  • Thiophene-bridged pyrenetetramine hole-transport material and application of same to perovskite solar cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1 Synthesis of a thiophene-bridged tetraaminepyrene hole transport material having a structural unit of formula II.

[0077] Its synthetic route is as follows figure 1 shown.

[0078]

[0079] Synthesis of intermediate (1):

[0080] Dissolve 1g of 4-iodoanisole, 300mg of p-bromoaniline, 40mg of 1,1'-bisdiphenylphosphinoferrocene, 20mg of palladium acetate and 200mg of sodium tert-butoxide in 20mL of toluene, and heat to reflux under the protection of nitrogen 12 hours. After cooling, the solvent was spin-dried, extracted three times with dichloromethane, and the organic phase was dried with anhydrous sodium sulfate. After the solvent was removed by rotary evaporation, column chromatography was separated and purified (eluent: petroleum ether / ethyl acetate 15 / 1, v / v) Intermediate (1) was obtained in 70% yield.

[0081] Synthesis of intermediate (2):

[0082] 100 mg of compound 1, 40 mg of 2-thiophene boronic acid, 4 mg of bistriphenylphosphine palladium d...

Embodiment 2

[0087] Example 2 Synthesis of a thiophene-bridged tetraaminepyrene hole transport material having a structural unit of formula III.

[0088] Its synthetic route is as follows figure 2 shown.

[0089]

[0090]

[0091] Synthesis of intermediate (4):

[0092] Dissolve 1g of 4-iodothioanisole, 300mg of p-bromoaniline, 28mg of 1,1'-bisdiphenylphosphinoferrocene, 17mg of palladium acetate and 200mg of sodium tert-butoxide in 20mL of toluene, and heat to reflux under nitrogen protection 12 hours. After cooling, the solvent was spin-dried, extracted three times with dichloromethane, and the organic phase was dried with anhydrous sodium sulfate. After the solvent was removed by rotary evaporation, column chromatography was separated and purified (eluent: petroleum ether / ethyl acetate 15 / 1, v / v) Intermediate (4) was obtained in 62% yield.

[0093] Synthesis of intermediate (5):

[0094] 100 mg of compound 4, 40 mg of 2-thiophene boronic acid, 4 mg of bistriphenylphosphine ...

Embodiment 3

[0099] Example 3 Synthesis of a thiophene-bridged tetraaminepyrene hole-transporting material having a structural unit of formula IV.

[0100] Its synthetic route is as follows image 3 shown.

[0101]

[0102] Synthesis of intermediate (7):

[0103] Dissolve 300mg of 1-ethyl-4-iodobenzene, 100mg of p-bromoaniline, 11mg of 1,1'-bisdiphenylphosphinoferrocene, 10mg of palladium acetate and 200mg of sodium tert-butoxide in 20mL of toluene. Heating under reflux for 12 hours. After cooling, the solvent was spin-dried, extracted three times with dichloromethane, and the organic phase was dried with anhydrous sodium sulfate. After the solvent was removed by rotary evaporation, column chromatography was separated and purified (eluent: petroleum ether / ethyl acetate 15 / 1, v / v) Intermediate (7) was obtained with a yield of 75%.

[0104] Synthesis of intermediate (8):

[0105] 204 mg of compound 7, 70 mg of 2-thiophene boronic acid, 7 mg of bistriphenylphosphine palladium dichlorid...

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Abstract

The invention discloses a thiophene-bridged pyrenetetramine hole-transport material and application of the same to a perovskite solar cell. The thiophene-bridged pyrenetetramine hole-transport material has a structural formula as shown in a formula I which is described in the specification. The hole-transport material has a thiophene-bridged triarylated amine unit which presents good dissolvability and good film forming ability in an organic solvent, a large conjugate plane structure is beneficial for effective improvement of the hole mobility of the material, and preparation cost is low. Thetesting results of physical properties, electrochemical performance and heat stability prove that the hole-transport material has good heat stability and can match with the energy level of perovskite.When the hole-transport material is applied to the perovskite solar cell as a hole-transport layer, good photoelectric conversion efficiency is obtained.

Description

technical field [0001] The invention relates to a thiophene-bridged tetraaminepyrene hole transport material and its application in perovskite solar cells. Background technique [0002] With the gradual aggravation of energy crisis and environmental pollution, people urgently need to find new alternative energy sources. Solar energy is the most abundant renewable and clean energy on the earth. The solar energy absorbed by the earth's surface every minute can meet the energy needs of human beings for a year. Therefore, the preparation of high-efficiency photoelectric conversion devices is undoubtedly one of the important methods to solve the problems of energy crisis and environmental pollution. Perovskite materials possess superior charge transport properties, long carrier diffusion distances, full-spectrum absorption, and high light absorption coefficients. This allows the material to efficiently absorb sunlight and efficiently generate photogenerated carriers while reduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/20H01L51/42H01L51/46
CPCC07D333/20H10K85/622H10K85/655H10K85/631H10K30/10Y02E10/549
Inventor 钟羽武邵将洋胡劲松葛倩庆
Owner INST OF CHEM CHINESE ACAD OF SCI
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