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Phthalonitrile derivative, preparation method thereof, metal phthalocyanine derivative and preparation method and application thereof

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

Active Publication Date: 2019-04-19
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Phthalonitrile derivative, preparation method thereof, metal phthalocyanine derivative and preparation method and application thereof
  • Phthalonitrile derivative, preparation method thereof, metal phthalocyanine derivative and preparation method and application thereof
  • Phthalonitrile derivative, preparation method thereof, metal phthalocyanine derivative and preparation method and application thereof

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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 cooled reaction solution was subjected to column chromatography, and eluted using an eluent (the volume ratio of petroleum ether, ethyl acetate and methanol was 10:1:0.5); the solution obtained by column chromatography was evaporating to dryness, and the product Transfer to the Soxhlet extractor, use ethanol as the solvent, wash at 120°C, after 20 hours, the color of the solvent turns yellow and dark, replace the solvent and repeat the operation 3 to 5 times; place the product of the previous step in a mixed sol...

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Abstract

The invention provides a phthalonitrile derivative and belongs to the technical field of hole-transport materials. The provided phthalonitrile derivative is 4-phthalonitrile-4',4'-dimethoxy triphenylamine and has a structure shown as a formula I. A 4',4'-dimethoxy triphenylamine group is introduced into the provided phthalonitrile derivative, correspondingly the hole mobility of the correspondingmetal phthalocyanine derivative is improved, and the metal phthalocyanine derivative corresponding to the provided phthalonitrile derivative has excellent stability and can obviously improve the stability of a perovskite solar cell and prolong the service life of the perovskite solar cell. Additionally, the introduced 4',4'-dimethoxy triphenylamine group improves the organic solubility of the metal phthalocyanine derivative corresponding to the phthalonitrile derivative, is suitable for film preparation through a cheap liquid-phase process, has good film forming property and 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 Applications(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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