Hole transport material and preparation method thereof, application of hole transport material, and perovskite solar cell containing hole transport material

A technology for hole transport materials and solar cells, applied in the field of solar cells, can solve the problems of poor solubility of hole transport materials, reduce stability, raise the HOMO energy level of polymers, etc., and achieve controllable optoelectronic properties and good film morphology. , the effect of high photoelectric conversion efficiency and external quantum efficiency

Active Publication Date: 2019-08-20
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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AI Technical Summary

Problems solved by technology

However, the electron-rich nature of the π-bridge will raise the HOMO energy level of the molecule and reduce its intrinsic stability
[0004] Application research of acceptor-donor-acceptor (A-D-A) configuration non-doped hole transport materials in high-efficiency perovskite solar cells (The Fifth Symposium on New Solar Cells, Ding Xingdong; Chen Cheng; Cheng Ming Li Huaming), which provides a class of ionic hole transport materials with A-D-A configuration, the introduction of terminal ionic electron-withdrawing material can effectively improve the hole mobility and conductivity of the material, but its preparation method is relatively Complex, and the final hole transport material has poor solubility, which is not conducive to application

Method used

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  • Hole transport material and preparation method thereof, application of hole transport material, and perovskite solar cell containing hole transport material
  • Hole transport material and preparation method thereof, application of hole transport material, and perovskite solar cell containing hole transport material
  • Hole transport material and preparation method thereof, application of hole transport material, and perovskite solar cell containing hole transport material

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0077] A hole transport material has the following structure:

[0078]

[0079] The preparation method is as follows:

[0080]

[0081] (1) Synthesis of compound 1: 4,4'-dimethoxydiphenylamine (458mg, 2.0mmol), p-bromoiodobenzene (848mg, 3.0mmol), Pd 2 (dba) 3 (92mg, 0.1mmol), dppf (54mg, 0.085mmol), sodium tert-butoxide (952mg, 10mmol), placed in a two-necked bottle; after pumping argon three times, add anhydrous toluene 20mL; react under argon protection After heating to reflux for 24 hours, the reaction system was cooled to room temperature, the solvent was spun out, and the initial product was further purified through a column to obtain compound 1 with a mass of 380 mg and a yield of 50%.

[0082] 1 H NMR (400MHz, CDCl 3 )δ: 7.26(d, J=8.9Hz, 2H), 7.05(d, J=8.9Hz, 4H), 6.84(d, J=8.9Hz, 4H), 6.81(d, J=8.9Hz, 2H) ,3.81(s,6H).

[0083] (2) Synthesis of Compound 2: Compound 1 (3.84g, 10mmol), bis(pinacolate) diboron (3.81g, 15mmol), Pd(dppf)Cl 2 (365mg, 0.5mmol), p...

preparation example 2

[0095] A hole transport material has the following structure:

[0096]

[0097] The preparation method is as follows:

[0098]

[0099] (1) Synthesis of compound 8: the synthetic steps refer to compound 4, and the yield is 82%.

[0100] 1 H NMR (400MHz, CDCl 3 ): δ7.63(d, J=5.3Hz, 2H), 7.30(d, J=5.4Hz, 2H), 4.43-4.36(m, 2H), 1.85-1.78(m, 2H), 1.51-1.28( m,18H),0.90(t,J=6.8Hz,3H).

[0101] (2) Synthesis of Compound 9: Compound 8 (200mg, 0.38mmol), N-bromosuccinimide (208mg, 1.16mmol) were placed in a two-necked flask; 7mL of anhydrous chloroform and anhydrous N were added, N'-dimethylformamide 2mL; After reacting at room temperature for 12 hours, pour it into water, extract with chloroform, combine the organic phases, dry with anhydrous sodium sulfate, spin out the solvent, and the initial product is further purified by column to obtain compound 9, mass It was 204 mg, and the yield was 80%.

[0102] 1 H NMR (400MHz, CDCl 3):δ7.22(s,2H),4.32-4.29(m,2H),1.80-1.72(m,...

preparation example 3

[0109] A hole transport material has the following structure:

[0110]

[0111] The preparation method is as follows:

[0112]

[0113] (1) Compound 12 was synthesized according to the method for compound 1 in Preparation Example 1, and the yield was 50%.

[0114] 1 H NMR (400MHz, CD 2 Cl 2 ):δ7.29-6.87(m,28H),3.81(s,12H).

[0115] (2) Compound 13 was synthesized according to the method for synthesizing Compound 2 in Preparation Example 1, with a yield of 61%.

[0116] 1 H NMR (400MHz, CDCl 3 ):δ7.64(br,2H),7.08-7.06(m,8H),6.97(br,6H),6.88-6.83(m,12H),3.81(s,12H),1.34(s,12H).

[0117] (3) Compound C was synthesized according to the method for compound A in Preparation Example 1, and the yield was 70%.

[0118] 1 H NMR (400MHz, CDCl 3 ): δ7.83(s, 2H), 7.45(d, J=8.7Hz, 4H), 7.09(d, J=8.9Hz, 16H), 7.03-6.99(m, 12H), 6.90(d, J= 8.9Hz,8H),6.86(d,J=8.9Hz,16H),4.26-4.22(m,2H),3.82(s,24H),1.76-1.72(m,2H),1.45-1.30(m,18H ), (t,J=7.0Hz,3H).

[0119] 13 C NMR (400MHz,...

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Abstract

The invention provides a hole transport material and a preparation method thereof, application of a hole transport material, and a perovskite solar cell containing a hole transport material. The holetransport material has structures shown in the formula I and/or the formula II. The hole transport material provided by the invention has excellent solubility and a good hole transport performance, can obtain a better film morphology, has adjustable photoelectric performance, and can be applied to perovskite solar cells.

Description

technical field [0001] The invention belongs to the technical field of solar cells, and relates to a hole transport material, a preparation method and application thereof, and a perovskite solar cell containing the same. Background technique [0002] In recent years, perovskite solar cells using organic-inorganic hybrid perovskite materials as "light harvesting agents" have achieved rapid development, which can convert solar energy into electrical energy at a lower cost, and have been favored by the global scientific research circle. Favored by the industrial circle, its energy conversion efficiency has also gradually increased, and has recently exceeded 24%. In perovskite solar cells, in addition to the active layer perovskite, the hole transport material is also very critical; the hole transport material can not only extract holes, but also transport holes, which is very important for improving the performance of the device. At present, most of the reported high-efficienc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/42H01L51/46
CPCH10K85/00H10K30/10H10K30/00Y02E10/549
Inventor 郭旭岗王漾何祝兵陈伟
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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