Metalloporphyrin-quinoxaline organic semiconductor material and preparation method and application thereof

An organic semiconductor, metalloporphyrin technology, applied in semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., can solve the problems of limiting the application scope of organic semiconductor materials, no literature and patent reports, etc., to achieve good thermal stability and Environmental stability, improved carrier mobility, and improved utilization effects

Active Publication Date: 2012-05-09
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-quinoxaline organic semiconduc

Method used

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  • Metalloporphyrin-quinoxaline organic semiconductor material and preparation method and application thereof
  • Metalloporphyrin-quinoxaline organic semiconductor material and preparation method and application thereof
  • Metalloporphyrin-quinoxaline organic semiconductor material and preparation method and application thereof

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preparation example Construction

[0045] The preparation method of metalloporphyrin-quinoxaline organic semiconductor material designed by the present invention, the steps are as follows:

[0046] 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 silfluorene porphyrin derivative (D), the reaction formula is as follows:

[0047]

[0048] Wherein, i:j:k=1:1~100:1~100, and i=j+k, i≥j>0; the first catalyst adopts organic acid, such as propionic acid, trifluoroacetic acid; the oxidizing agent can adopt two Chlorodicyanobenzoquinone (DDQ), the first organic solvent can be one or both in chloroform or dichloromethane;

[0049] Step S2: Dissolve the silicon fluorene porphyrin derivative (D) obtained i...

Embodiment 1

[0069] This embodiment discloses a silicon fluorene zinc porphyrin-quinoxaline organic semiconductor material with the following structure

[0070]

[0071] In the above formula, n=10;

[0072] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0073] 1. Synthesis of 5,8-dibromo-2,3-bis(phenyl)quinoxaline

[0074]

[0075]3,6-Dibromo-o-phenylenediamine (1.01 g, 3.7 mmol) was added to a solution of the compound diphenylethanedione (0.39 g, 1.8 mmol) in 20 ml of acetic acid at 120°C. Reflux overnight, pour the reaction solution into water, and neutralize to neutral with sodium bicarbonate. Extracted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the crude product was obtained by column chromatography as a white solid. Then recrystallized from chloroform / n-hexane to obtain a white solid powder with a yield of 86%.

[0076] GC-MS (EI-m / z)...

Embodiment 2

[0097] This embodiment discloses a silicon fluorene iron porphyrin-quinoxaline organic semiconductor material with the following structure

[0098]

[0099] In the above formula, n=28;

[0100] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0101] One, the synthesis of 5,8-bis(tributyltin)-2,3-bis(phenyl)quinoxaline

[0102] Its preparation sees embodiment 1 for details.

[0103] 2. Synthesis of 5-(9'-methyl-9'-hexadecyl)silafluorene-15-(9'-docosyl)silafluorene porphyrin

[0104]

[0105] 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...

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Abstract

The invention belongs to the field of an optoelectronic material, and discloses a metalloporphyrin-quinoxaline organic semiconductor material and a preparation method and an application thereof. The metalloporphyrin-quinoxaline organic semiconductor material is shown in Formula (I), wherein n is an integer between 1 and 100, R1, R2, R3 and R4 are H, C1-C32 alkyl, phenyl and alkyl benzene or alkoxy benzene containing one or more C1-C32, and M is a metal ion. The metalloporphyrin-quinoxaline organic semiconductor material has a broad scope of light absorption, and the rate of utilization of sunlight can be increased. The metalloporphyrin-quinoxaline organic semiconductor material also has better thermal stability and environmental stability. In addition, the process of the preparation method is simple and is easy to operate and control.

Description

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

Claims

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Application Information

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