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A phthalocyanine derivative and its preparation method, a metal phthalocyanine derivative and its preparation method and application

A technology of metal phthalocyanine and derivatives, applied in the field of hole transport materials

Active Publication Date: 2021-11-02
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned phthalocyanine-based hole transport materials need to be doped to achieve high conversion efficiency.

Method used

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  • A phthalocyanine derivative and its preparation method, a metal phthalocyanine derivative and its preparation method and application
  • A phthalocyanine derivative and its preparation method, a metal phthalocyanine derivative and its preparation method and application
  • A phthalocyanine derivative and its preparation method, a metal phthalocyanine derivative and its preparation method and application

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preparation example Construction

[0032] The present invention also provides a method for preparing the phthalocyanine derivative described in the above technical scheme, comprising the following steps: in a protective atmosphere, 4-bromo-phthalonitrile and 4-boronic acid ester-4', 4'-dimethoxytriphenylamine undergoes a coupling reaction to obtain 4-phthalocyano-4',4'-dimethoxytriphenylamine. The reaction formula is shown in formula (1):

[0033]

[0034] In the present invention, the mass ratio of 4-bromo-phthalonitrile to 4-boronate-4',4'-dimethoxytriphenylamine is preferably 1:4-5.

[0035] In the present invention, the solvent of the coupling reaction is preferably a mixed solution of water and tetrahydrofuran, and the volume ratio of the water and tetrahydrofuran is preferably 3:50; the catalyst used in the coupling reaction is preferably tetrakis(triphenylphosphine ) palladium, the mass ratio of the catalyst to 4-bromo-phthalonitrile is preferably 1:0.5~0.7; the coupling reaction is preferably carrie...

Embodiment 1

[0070] 4-Bromo-phthalonitrile (0.414g), 4-boronate-4',4'-dimethoxytriphenylamine (1.725g), tetrakis(triphenylphosphine)palladium (0.231g) and Potassium carbonate (2.764g) was placed in a mixed solution of water (3mL) and tetrahydrofuran (50mL), and nitrogen was used as a protective gas, and inflated-degassed three times to obtain a nitrogen protective atmosphere, and then kept stirring at 80°C for 12h, and the reaction was completed Afterwards, the reaction solution was cooled to room temperature, and magnesium sulfate was added to remove water; the solution after water removal was spin-dried to obtain a solid product, and an eluent (petroleum ether: ethyl acetate: the volume ratio of dichloromethane was 20:1: 2) The obtained solid product is subjected to column chromatography; after the column chromatography is completed, the obtained solution is spin-dried to obtain an o-phthalocyanine derivative. According to nuclear magnetic analysis, its structure is shown in formula I, wh...

Embodiment 2

[0073]The phthalocyanine derivative (1g) obtained in Example 1 and anhydrous cuprous chloride (104mg) were mixed according to a molar ratio of 3:1 and placed in 5mL of n-hexanol, and 0.5mL of 1,8-diazabicyclo [5.4.0] Undec-7-ene, using nitrogen as a protective gas, inflated-degassed three times to obtain a protective gas atmosphere, and then kept stirring at 150 ° C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution after cooling is carried out column chromatography, uses eluent (the volume ratio of sherwood oil, ethyl acetate and methanol is 10:1:0.5) to carry out elution; The solution obtained by column chromatography is rotary evaporated to dryness, product Transfer to a Soxhlet extractor, use ethanol as a solvent, and wash at 120°C. After 20 hours, the color of the solvent turns yellow and dark, and the solvent is replaced for 3 to 5 times; the product of the previous step is placed in a mixed solution...

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Abstract

The invention provides a phthalocyanine derivative and belongs to the technical field of hole transport materials. The phthalocyanine derivative provided by the present invention is 4-phthalocyanine-4',4'-dimethoxytriphenylamine, which has the structure shown in formula I. The o-phthalocyanine derivatives provided by the present invention introduce 4',4'-dimethoxytriphenylamine groups, which improves the hole mobility of the corresponding metal phthalocyanine derivatives, and the o-phthalocyanine derivatives provided by the invention The metal phthalocyanine derivatives corresponding to phthalocyanine derivatives have excellent stability, which can significantly improve the stability and lifetime of perovskite solar cells. In addition, the introduction of 4',4'-dimethoxytriphenylamine groups improves the organic solubility of phthalocyanine derivatives to metal phthalocyanine derivatives, which is suitable for the preparation of thin films by cheap liquid phase processes, and has good film-forming properties. It can be directly prepared in a large area.

Description

technical field [0001] The invention relates to the technical field of hole transport materials, in particular to an o-phthalocyanine derivative and a preparation method thereof, a metal phthalocyanine derivative and a preparation method and application thereof. Background technique [0002] In recent years, a new type of solar cell using perovskites (Perovskites) as a light-absorbing material has developed rapidly. The research upsurge of organic-inorganic hybrid perovskite materials started from its outstanding application effect in photovoltaic solar cells. In 2009, the Miyasaka research group used CH for the first time 3 NH 3 PB 3 A solar cell with a sensitized structure was prepared, and a photoelectric conversion efficiency of 3.8% was obtained, setting off the curtain of research on perovskite materials and devices. In 2013, perovskite solar cells were rated as one of the top ten scientific breakthroughs of the year by the US magazine Science. So far, the highest...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/58C07C253/30C07D487/22H01L51/42H01L51/46
CPCC07C255/58C07D487/22H10K85/371H10K30/10H10K30/40Y02E10/549
Inventor 许宗祥冯垚淼胡启锟
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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