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Metal porphyrin-diazosulfide organic semiconductor material as well as preparation method and application thereof

A technology of benzothiadiazole and organic semiconductors, applied in semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., can solve the problems of limiting the application range of organic semiconductor materials, lack of literature and patent reports, etc., and achieve good thermal stability Enhanced performance and environmental stability, improved carrier mobility, and expanded application range

Inactive Publication Date: 2013-07-03
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

[0006] However, there are still no literature and patent reports on metalloporphyrin-benzothiadiazole organic semiconductor materials containing silfluorene, which greatly limits the application range of organic semiconductor materials.

Method used

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  • Metal porphyrin-diazosulfide organic semiconductor material as well as preparation method and application thereof
  • Metal porphyrin-diazosulfide organic semiconductor material as well as preparation method and application thereof
  • Metal porphyrin-diazosulfide organic semiconductor material as well as preparation method and application thereof

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preparation example Construction

[0043] The preparation method of metalloporphyrin-benzothiadiazole organic semiconductor material designed by the present invention, the steps are as follows:

[0044] Step S1: Dissolving dipyrromethane (a), the first silafluorene derivative (b) and the second silafluorene derivative (c) in a molar ratio i:j:k in the first organic compound containing the oxidizing agent and the first catalyst Solvent, at a temperature of 20-100°C, react for 1-24 hours to obtain a silfluorene porphyrin derivative (d); in the formula, R 1 , R 2 , R 3 , R 4 for H, C 1 -C 32 Alkyl, phenyl, containing one or more C 1 -C 32 Alkylbenzene or alkoxybenzene; the reaction formula is as follows:

[0045]

[0046] Wherein, i:j:k=1:1~100:1~100, and i=j+k, i≥j>0; the first catalyst is propionic acid, trifluoroacetic acid; the oxidizing agent is dichloro Dicyanobenzoquinone; the first organic solvent is one or both of chloroform and dichloromethane;

[0047] Step S2: Add the silicon fluorene porph...

Embodiment 1

[0065] This embodiment discloses a silicon fluorene zinc porphyrin-benzothiadiazole organic semiconductor material with the following structure

[0066]

[0067] In the above formula, n=78;

[0068] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0069] 1. Synthesis of 4,7-bis(tributyltin)-2,1,3-benzothiadiazole

[0070]

[0071] In a 500mL three-necked flask, add 1.21g of 4,7-dibromo-2,1,3-benzothiadiazole, 400mL of tetrahydrofuran, cool the system down to -30°C, add dropwise 3.5mL of n-butyllithium (2.5 M), then react at -30°C for 1h, and then add SnBu at one time 3Cl 2.68g, reacted at -30°C for 30min, then naturally warmed to room temperature, and stirred overnight. The reactant was poured into ice water, extracted with ether, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the product was separated by column chromatography with silica gel / petroleum ether (30-60° C.) to ...

Embodiment 2

[0090] This embodiment discloses a silicon fluorene iron porphyrin-benzothiadiazole organic semiconductor material with the following structure

[0091]

[0092] In the above formula, n=56;

[0093] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0094] 1. Synthesis of 4,7-bis(tributyltin)-2,1,3-benzothiadiazole

[0095] Its preparation sees embodiment 1 for details.

[0096] 2. Synthesis of 5-(9'-methyl-9'-hexadecyl)silafluorene-15-(9'-docosyl)silafluorene porphyrin

[0097]

[0098] Set up an anhydrous and oxygen-free device, weigh the intermediates 2-aldehyde-9-methyl-9-hexadecylsilafluorene (0.45g, 1mmol), 2-aldehyde-9-docosylsilafluorene ( 0.66g, 1mmol), dipyrromethane (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 dichlorodicyanobenzene Quinone (DDQ) (1.82g, 8mmol), continue stirring at room temp...

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Abstract

The invention belongs to the field of photoelectron materials, which discloses a metal porphyrin-diazosulfide organic semiconductor material as well as a preparation method and application thereof. The metal porphyrin-diazosulfide organic semiconductor material has a structural formula (P), wherein n is an integer from 1-100, R1, R2, R3 and R4 is H, the alkyl of C1-C32, phenyl and alkylbenzene oralkoxy benzene containing one or a plurality of C1-C32, and M is a metal ion. The metal porphyrin-diazosulfide organic semiconductor material provided by the invention has the advantages of good filmforming property, strong absorbance and wide light absorption range, and the use ratio of the metal porphyrin-diazosulfide organic semiconductor material on sunlight is improved. The metal porphyrin-diazosulfide organic semiconductor material has better thermal stability and environment stability. In addition, the preparation method has a simple technology and is easy to operate and control.

Description

technical field [0001] The invention relates to an organic semiconductor material, more specifically to a metalloporphyrin-benzothiadiazole organic semiconductor material. [0002] The invention also relates to the preparation method and application of the metalloporphyrin-benzothiadiazole organic semiconductor material. 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 good...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07F7/10C09K11/06H01L51/30H01L51/46H01L51/54H01S5/36
CPCY02E10/549
Inventor 周明杰黄杰刘贻锦
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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