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Metal phthalocyanine compound and application thereof in solar cell

A metal phthalocyanine and compound technology, applied to metal phthalocyanine compounds and their application in solar cells, can solve problems such as poor stability and damage

Pending Publication Date: 2022-05-13
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the biggest problem facing the commercialization of perovskite solar cells is poor stability. Perovskite is easily damaged by water vapor and oxygen in the air.

Method used

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  • Metal phthalocyanine compound and application thereof in solar cell
  • Metal phthalocyanine compound and application thereof in solar cell
  • Metal phthalocyanine compound and application thereof in solar cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of embodiment 1 compound 1

[0041]

[0042] Potassium carbonate (2eq.), 0.05mol (1eq.) of 4-nitrophthalonitrile and (2eq.) was mixed in 25mlDMF, stirred at 60°C for 24 hours, and monitored by spot plate. After the reaction was completed, extracted with water / ethyl acetate, collected the ethyl acetate phase, removed the solvent by rotary evaporation, and separated by silica gel column chromatography (dichloro / ethyl acetate) Petroleum ether=1 / 1) to obtain ether-substituted phthalonitrile. Combine 0.05mol (1eq.) of ether-substituted phthalonitrile, DBU (1eq.) and 5ml of n-pentanol, and keep it under argon at 150°C for 48 hours. After the reaction is completed, the solvent is removed by distillation under reduced pressure, and evaporated to dryness to obtain The viscous material was diluted with ethanol, and a large amount of water was added to precipitate the solid, which was centrifuged and dried. Afterwards, metal-free phthalocyanine (Pc) was obtaine...

Embodiment 2-6

[0043] The synthesis of embodiment 2-6 compound 2-6

[0044]

[0045]

[0046] Compounds 2-6 were prepared respectively according to the method of Example 1, the only difference being that replace with Compound 2, MS calcd.forC 48 h 48 N 8 o 8 Cu m / z 922.29, found 923.24. Compound 3, MS calcd.for C 48 h 48 N 8 o 8 Cu m / z 922.29, found 923.42. Compound 4, MS calcd.for C 48 h 48 N 8 o 8 Cu m / z 922.29, found 923.36. Compound 5, MS calcd.for C 44 h 40 N 8 o 8 Cu m / z 871.23, found 872.34. Compound 6, MS calcd.forC 44 h 40 N 8 o 4 S 4 Cu m / z 935.14, found 936.50.

Embodiment 7-12

[0047] The synthesis of embodiment 7-12 compound 7-12

[0048]

[0049] Compounds 7-12 were prepared according to the method of Example 1, except that copper acetate was replaced by zinc acetate. Compound 7, by NMR: 1 H NMR (400MHz, DMSO-d) δ 7.45-8.54 (d, 3H), 4.01 (d, 1H), 1.89-2.35 (m, 2H), 1.24-2.01 (m, 6H). MS calcd.for C 48 h 48 N 8 o 8 Zn m / z 928.29, found 929.35. Compound 8, by NMR: 1 H NMR (400 MHz, DMSO-d) δ 7.65-8.86 (d, 3H), 3.58 (t, 1H), 1.99-2.86 (m, 2H), 1.11-1.65 (m, 6H). MS calcd.for C 48 h 50 N 8 o 8 Zn m / z 928.29, found 929.18. Compound 9, by NMR: 1 H NMR (400 MHz, DMSO-d) δ 7.58-8.87 (d, 3H), 3.87 (t, 2H), 1.99-2.57 (m, 4H), 1.26 (t, 3H). MS calcd.for C 48 h 50 N 8 o 8 Zn m / z 928.29, found 929.54. Compound 10, by NMR: 1 H NMR (400 MHz, DMSO-d) δ 7.87-8.74 (d, 3H), 3.89 (t, 2H), 2.24-2.61 (m, 2H), 1.51 (t, 3H). MScalcd.for C 44 h 40 N 8 o 8 Zn m / z 872.23, found 873.61. Compound 11, by NMR: 1 H NMR (400 MHz, DMSO-d) δ 7.12-7.82 (...

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Abstract

The invention relates to a metal phthalocyanine compound and application thereof in a solar cell. The phthalocyanine compound is shown as a formula I, R1, R2, R3 and R4 are respectively and independently hydrogen, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkylthio, amino, C1-C10 alkyl substituted amino, halogen or R5-G1-L-G2-, at least one of R1, R2, R3 and R4 is R5-G1-L-G2-, L is C1-C5 alkylene, R5 is C1-C5 alkyl, G1 and G2 are respectively and independently O, S or NR, and R1, R2, R3 and R4 are respectively and independently hydrogen, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkylthio, amino, C1-C10 alkyl substituted amino, halogen or R5-G1-L-G2-, and at least one of R1, R2, R3 and R4 is R5-G1-L-G2-. R is hydrogen, C1-C5 alkyl, C1-C5 alkoxy, C1-C5 alkylthio, C1-C5 alkyl substituted amino or R6-G3-L '-, R6 is C1-C5 alkyl, G3 is O or S, L' is C1-C5 alkylene, and M is copper or zinc.On the basis of maintaining the original stability of the phthalocyanine compound, the efficiency of the assembled perovskite solar cell is improved by adjusting the structure of the phthalocyanine compound.

Description

technical field [0001] The invention belongs to the field of batteries, and in particular relates to a metal phthalocyanine compound and its application in solar batteries. Background technique [0002] With the development of the times, it is difficult for limited fossil energy to meet people's growing production and living needs for a long time. There is a continuous source of sunlight, and it is a very promising way to use solar cells to obtain energy from it. [0003] The emerging perovskite solar cells are the new darling in the field of optoelectronics, with high photoelectric conversion efficiency, easy processing and low cost and other excellent features, and are the most potential substitutes for crystalline silicon solar cells. [0004] At present, the development of perovskite solar cells is very rapid, and the efficiency of small-area devices in the laboratory is close to the highest efficiency of silicon cells. However, the industrialization of perovskite solar...

Claims

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Application Information

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IPC IPC(8): C07D487/22H01L51/46H01L51/42
CPCC07D487/22H10K85/371H10K85/381H10K30/00Y02E10/549
Inventor 曹靖李春伶于泽峰
Owner LANZHOU UNIVERSITY