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Metalloporphyrin-thienopyrazine organic semiconductor material, preparation method thereof and application thereof

A technology of organic semiconductors and metalloporphyrins, applied in semiconductor/solid-state device manufacturing, semiconductor devices, luminescent materials, 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 and Effects of environmental stability, improvement of carrier mobility, and expansion of application range

Active Publication Date: 2012-05-16
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

[0007] However, there are still no literature and patent reports on metalloporphyrin-thienopyrazine organic semiconductor materials containing silfluorene, which greatly limits the application range of organic semiconductor materials.

Method used

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  • Metalloporphyrin-thienopyrazine organic semiconductor material, preparation method thereof and application thereof
  • Metalloporphyrin-thienopyrazine organic semiconductor material, preparation method thereof and application thereof
  • Metalloporphyrin-thienopyrazine organic semiconductor material, preparation method thereof and application thereof

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preparation example Construction

[0044] The preparation method of metalloporphyrin-thienopyrazine organic semiconductor material designed by the present invention, the steps are as follows:

[0045] 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 In the solvent, add an oxidizing agent and a first catalyst to the first organic solvent, and react at 20-100° C. for 1-24 hours to obtain a silicon fluorene porphyrin derivative (D), wherein, i:j:k= 1: 1~100: 1~100, and i=j+k, i≥j>0; the first catalyst adopts organic acid, as propionic acid, trifluoroacetic acid; Oxidant can adopt dichlorodicyanobenzoquinone (DDQ ), the first organic solvent can be one or both in chloroform or dichloromethane; Reaction formula is as follows:

[0046]

[0047] Step S2: Dissolve the silicon fluorene porphyrin derivative (D) obtained in step S1 and the br...

Embodiment 1

[0066] This embodiment discloses a silicon fluorene zinc porphyrin-thienopyrazine organic semiconductor material with the following structure

[0067]

[0068] In the above formula, n=10;

[0069] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0070] 1. Synthesis of 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) base thieno[3,4-b]pyrazine

[0071]

[0072] Under the protection of argon, add p-5,7-dibromothieno[3,4-b]pyrazine (8.8g, 0.03mol) into the three-necked flask, add 200ml of tetrahydrofuran solvent, and at -78°C Slowly inject n-butyllithium (25.2mL, 2.5M, 0.06mol) with a syringe, continue to stir the reaction for 2h, inject 2-isopropoxy-4,4,5,5- Tetramethyl-1,3,2-dioxaborolane (13 mL, 0.06 mol), stirred overnight at room temperature. 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...

Embodiment 2

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

[0091]

[0092] In the above formula, n=28;

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

[0094] 1. Synthesis of 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) base thieno[3,4-b]pyrazine

[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, helium gas for 30min, add 2ml of trifluoroacetic acid into the syringe, stir at 100°C for 1h, then add dichlorodicyano Benzoquinone (DDQ) (1.82g, 8mmol), continued to ...

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Abstract

The invention which belongs to the photoelectron material field discloses a metalloporphyrin-thienopyrazine organic semiconductor material, a preparation method thereof and an application thereof. The structural formula of the metalloporphyrin-thienopyrazine organic semiconductor material is represented by formula (I). In the formula (I), n is an integer between 1 and 100; R1, R2, R3 and R4 are H, C1-C32 alkyl, phenyl and alkylbenzene or alkoxybenzene containing one or more C1-C32 respectively; and M is a metallic ion. The metalloporphyrin-thienopyrazine organic semiconductor material provided in the invention, which has a wide light absorption range, allows the utilization rate to sunlight to be improved and has the advantages of good thermal stability and good environment stability. In addition, the preparation method of the material has the advantages of simple process, easy operation and easy control.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to a metalloporphyrin-thienopyrazine organic semiconductor material. [0002] The invention also relates to the preparation method and application of the metal porphyrin-thienopyrazine 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 photovol...

Claims

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Application Information

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