Porphyrin-pyrrolopyrrole copolymer containing carbazole, preparation method thereof and application thereof

A technology of pyrrolopyrrole copolymer and bromophenylpyrrolopyrrole diketone, which is applied in the field of copolymers, can solve the problems of lack of literature and patent reports, limit the scope of application, etc., achieve improved solubility, expand the scope of application, and mild reaction conditions Effect

Inactive Publication Date: 2012-02-08
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, there are still no literature and patent reports on porphyrin-pyrrolopyrrole copolymerized organic semiconductor materials containing carbazole, which greatly limits their application range.

Method used

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  • Porphyrin-pyrrolopyrrole copolymer containing carbazole, preparation method thereof and application thereof
  • Porphyrin-pyrrolopyrrole copolymer containing carbazole, preparation method thereof and application thereof
  • Porphyrin-pyrrolopyrrole copolymer containing carbazole, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0048] A preparation method of carbazole-containing porphyrin-pyrrolopyrrole copolymer, comprising the steps of:

[0049] The preparation method of the carbazole-containing porphyrin-pyrrolopyrrole copolymer designed by the present invention, the steps are as follows:

[0050] Step S1, providing 5,15-dibromo-10,20-alkylcarbazole porphyrin of structural formula (A) and (4,4,5,5-tetramethyl-1,3,2 - dioxaborolane) substituted 3,6-di-p-bromophenylpyrrolopyrrole diketopes:

[0051]

[0052] In the formula: n is an integer between 1-100, R 1 , R 2 , R 3 , R 4 Hydrogen or C 1 -C 32 Alkyl, phenyl, C 1 -C 32 Alkylbenzene or alkoxybenzene.

[0053] Step S2, in an oxygen-free environment (in the present invention, the oxygen-free environment is composed of nitrogen and / or inert gas), under the condition that the first catalyst and the first organic solvent exist, the 5,15-dibromo- 10,20-alkylcarbazole porphyrin and (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) substituted 3,6-tw...

Embodiment 1

[0072] This example discloses a 10,20-bis(9'-octylcarbazole)porphyrin-3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dioctyl with the following structure Diketone-based organic semiconductor materials (n=10)

[0073]

[0074] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0075] 1. Synthesis of 5,15-two (9'-octylcarbazole) porphyrin

[0076]

[0077]Set up an anhydrous and oxygen-free device, weigh the intermediate 2-aldehyde-9-octylcarbazole (0.31g, 1mmol) and dipyrromethane (0.15g, 1mmol), dissolve it in 250ml of dichloromethane, and pass it into nitrogen 30min, add 1ml of propionic acid into the syringe, stir at 20°C for 24h, then add dichlorodicyanobenzoquinone (DDQ) (0.91g, 4mmol), continue stirring at room temperature for 30min, then add 1ml of triethylamine to quench the reaction, Concentrate the solvent, filter, collect the filtrate and spin dry the solvent, rinse quickly with dichloromethane on the silica gel column, spin ...

Embodiment 2

[0095] This example discloses a 10-(9'-methylcarbazole)-20-(9'-docosylcarbazole)porphyrin-3,6-diphenylpyrrolo[3, 4-c] Pyrrole-1-octyl-4-hexadecyldione organic semiconductor material (n=56)

[0096]

[0097] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0098] One, the synthesis of 5-(9'-methylcarbazole)-15-(9'-docosylcarbazole) porphyrin

[0099]

[0100] Set up an anhydrous and oxygen-free device, weigh the intermediate 2-aldehyde-9-methylcarbazole (0.21g, 1mmol), 2-aldehyde-9-docosylcarbazole (0.65g, 1mmol), di Pyrromethane (0.30g, 2mmol), dissolved in 250ml of dichloromethane, blown nitrogen for 30min, added 2ml of trifluoroacetic acid into the syringe, stirred at 100°C for 1h, then added dichlorodicyanobenzoquinone (DDQ) (1.82g , 8mmol), continue to stir at room temperature for 30min, then add 2ml of pyridine to quench the reaction, concentrate the solvent, filter, collect the filtrate and spin-dry the solvent, use di...

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Abstract

The invention which belongs to the field of photoelectronic materials discloses a porphyrin-pyrrolopyrrole copolymer containing carbazole, a preparation method thereof and an application thereof. The structural formula of the copolymer is represented by formula (I); and in the formula (I), n is an integer between 1 and 100, and R1, R2, R3, and R4 are hydrogen, C1-C32 alkyl, phenyl, or C1-C32 alkylphenyl or alkyloxyphenyl. Groups which allow the solubility to be increased, such as alkyl, are introduced to a porphyrin-thiophenethiadiazole copolymer containing carbazole provided in the inventionat the 2-position and the 5-position to improve the solubility and the film forming ability of a material (the porphyrin-thiophenethiadiazole copolymer), and substituents at the 3-position and the 6-position are changed to regulate the light absorption range of pyrrolopyrrole dione, so the application range of the porphyrin-thiophenethiadiazole copolymer and pyrrolopyrrole dione in fields of organic solar cells and the like is enlarged; and simultaneously long chain alkyl is introduced to improve the solubility of the material.

Description

technical field [0001] The invention relates to a copolymer, more specifically to a carbazole-containing porphyrin-pyrrolopyrrole copolymer that can be used as a semiconductor material. [0002] The invention also relates to the preparation method and application of the carbazole-containing porphyrin-pyrrolopyrrole copolymer. Background technique [0003] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. Due to the complex production process and high cost of silicon cells currently used on the ground, their application is limited. In order to reduce the cost of batteries and expand the application range, people have been looking for new solar cell materials for a long time. Organic semiconductor materials have attracted much attention due to the advantages of readily available raw materials, low cost, simple preparation process, good environmental stability, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D487/22C07F5/02C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰黄杰刘贻锦
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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