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Copolymer material containing carbazole porphyrin-triphenylamine and preparation method and application thereof

A technology of carbazole porphyrin and triphenylamine, which is applied in the field of carbazole porphyrin-triphenylamine-containing copolymer material and its preparation, and can solve the problem of low conversion efficiency of inorganic solar cells, mismatched spectral response, and low carrier electrodes. Collection efficiency and other issues

Inactive Publication Date: 2013-03-27
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since 1992, N.S.Sariciftci etc. reported the light-induced electron transfer phenomenon between conjugated polymers and C60 on SCIENCE (N.S Sariciftci, L.Smilowitz, A.J.Heeger, et al.Science, 1992,258,1474), people in A lot of research has been invested in polymer solar cells and rapid development has been achieved, but the conversion efficiency of polymer solar cells is still much lower than that of inorganic solar cells
The main constraints that limit the improvement of performance are: the spectral response of organic semiconductor materials does not match the spectrum of solar radiation, the relatively low carrier mobility of organic semiconductors, and the low electrode collection efficiency of carriers, etc.

Method used

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  • Copolymer material containing carbazole porphyrin-triphenylamine and preparation method and application thereof
  • Copolymer material containing carbazole porphyrin-triphenylamine and preparation method and application thereof
  • Copolymer material containing carbazole porphyrin-triphenylamine and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] This embodiment discloses a 10,20-di(9-octylcarbazole) porphyrin-triphenylamine copolymer material (n=52) with the following structure:

[0050]

[0051] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0052] One, the synthesis of 4,4'-two (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) triphenylamine:

[0053]

[0054] Under the protection of nitrogen, add p-4,4'-dibromotriphenylamine (8.0g, 0.02mol) into the three-necked flask, then add 150ml of tetrahydrofuran solvent, and slowly inject n-butyl Lithium (16.8mL, 2.5M, 0.04mol), continue to stir the reaction for 2h, inject 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2 - Dioxaborolane (8.7mL, 0.04mol), stirred at room temperature for 6h-16h. Saturated aqueous sodium chloride (30ml) was added to terminate the reaction, extracted with chloroform, dried over anhydrous sodium sulfate, and filtered, the filtrate was collected and the solvent was evaporated off. Finally, the crude pro...

Embodiment 2

[0065] This embodiment discloses a 10-(9-methylcarbazole)-20-(9-dodecylcarbazole) porphyrin triphenylamine copolymer material (n=9) with the following structure:

[0066]

[0067] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0068] One, the synthesis of 4,4'-two (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) triphenylamine:

[0069] Its preparation sees embodiment 1 for details.

[0070] Two, the synthesis of 5-(9-methylcarbazole)-15-(9-docosylcarbazole) porphyrin:

[0071]

[0072] 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...

Embodiment 3

[0080] This embodiment discloses a 10-carbazole-20-(9-hexadecylcarbazole) porphyrin triphenylamine copolymer material (n=100) with the following structure:

[0081]

[0082] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0083]One, the synthesis of 4,4'-two (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) triphenylamine:

[0084] Its preparation sees embodiment 1 for details.

[0085] Two, the synthesis of 5-carbazole-15-(9-hexadecylcarbazole) porphyrin:

[0086]

[0087] Set up an anhydrous and oxygen-free device, weigh intermediate 2-aldehyde carbazole (0.20g, 1mmol), 2-aldehyde-9-hexadecylcarbazole (0.42g, 1mmol), dipyrromethane (0.30g, 2mmol ), dissolved in 300ml of dichloromethane, fed nitrogen for 30min, added 2ml of trifluoroacetic acid into a syringe, stirred at room temperature for 3h, then added dichlorodicyanobenzoquinone (DDQ) (1.82g, 8mmol), and continued to Stir for 30min, then add 2ml triethylamine to quench the r...

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Abstract

The invention relates to a copolymer material containing carbazole porphyrin-triphenylamine and a preparation method and application thereof. The copolymer material has a structural formula (III) shown in the specification, wherein n is an integral number of between 1 and 100; R1 and R2 are H or alkyl groups having 1 to 32 carbon atoms. In the copolymer material with the structural formula, the advantages of carbazole, porphyrin and triphenylamine compounds are fully utilized, so the copolymer material has the high energy conversion efficiency, and can be widely applied to fields of organic semiconductor materials, polymer solar cells, organic electrofluorescence, organic field effect transistors, organic laser storage, organic non-linear materials, organic laser and the like.

Description

【Technical field】 [0001] The invention relates to the field of organic semiconductor materials, in particular to a carbazole-containing porphyrin-triphenylamine copolymer material and its preparation method and application. 【Background technique】 [0002] 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 traditional silicon cells used for the ground, its 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 good photovoltaic effect. Since 1992, N.S.Sariciftci etc. reported the light-induced electron transf...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/54H01L51/30H01L51/46
CPCY02E10/50Y02E10/549
Inventor 周明杰黄杰刘贻锦
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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