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

An organic semiconductor and metalloporphyrin technology, which is used in the manufacture of semiconductor/solid-state devices, semiconductor devices, light-emitting materials, etc., can solve the problems of limiting the application scope of organic semiconductor materials, no literature and patent reports, etc., and achieves good thermal stability and Environmental stability, improved carrier mobility, good film-forming effects

Active Publication Date: 2013-11-27
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

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

Method used

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

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preparation example Construction

[0040] The preparation method of metalloporphyrin-thienothiadiazole organic semiconductor material designed by the present invention, the steps are as follows:

[0041] Step S1. Dissolve 5,7-dibromothieno[3,4-c][1,2,5]thiadiazole (s) in the first organic solvent, and cool down to - with liquid nitrogen / isopropanol 78°C, then add n-butyllithium (n-BuLi) dropwise, and react at -78°C for 1-5 hours, then add 2-isopropoxy-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane (x) or the structural formula is The bis-pinacolate diboron, continued to react at -78 ° C for 0.5-5 hours, then naturally warmed to room temperature, and reacted for 1-48 hours to obtain 5,7-bis(4,4,5,5-tetramethyl Base-1,3,2-dioxaborolane)ylthieno[3,4-c][1,2,5]thiadiazole (g); wherein, the first organic solvent is tetrahydrofuran , ether or at least one of dioxane; the molar ratio of 4,7-bis(tributyltin)-2,1,3-thienothiadiazole to tri-n-butyltin chloride is 1:1 ~10; the reaction formula is as follows:

[0042]

[...

Embodiment 1

[0058]This embodiment discloses a silicon fluorene zinc porphyrin-thienothiadiazole organic semiconductor material with the following structure

[0059]

[0060] In the above formula, n=40;

[0061] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0062] 1. 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) thieno[3,4-c][1,2,5] Synthesis of Thiadiazoles

[0063]

[0064] Under the protection of nitrogen, add p-5,7-dibromothieno[3,4-c][1,2,5]thiadiazole (8.8g, 0.03mol) into the three-necked flask, add 200ml of tetrahydrofuran solvent , slowly inject n-butyllithium (25.2mL, 2.5M, 0.06mol) with a syringe at -78°C, continue to stir the reaction for 2h, inject 2-isopropoxy-4 with a syringe at -78°C , 4,5,5-tetramethyl-1,3,2-dioxaborolane (13mL, 0.06mol), stirred overnight at room temperature. Saturated aqueous sodium chloride (30ml) was added to terminate the reaction, extracted with chloroform, dried over anhydrous sodium sulfat...

Embodiment 2

[0082] This embodiment discloses a silicon fluorene iron porphyrin-thienothiadiazole organic semiconductor material with the following structure

[0083]

[0084] In the above formula, n=56;

[0085] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0086] 1. 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) thieno[3,4-c][1,2,5] Synthesis of Thiadiazoles

[0087] Its preparation sees embodiment 1 for details.

[0088] 2. Synthesis of 5-(9'-methyl-9'-hexadecyl)silafluorene-15-(9'-docosyl)silafluorene porphyrin

[0089]

[0090] 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) (1.82...

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Abstract

The invention belongs to the field of optoelectronic materials and discloses a metalloporphyrin-thienothiadiazole organic semiconductor material and a preparation method and application thereof. The metalloporphyrin-thienothiadiazole organic semiconductor material has a structural formula (P) shown in the specification, wherein in the formula, n is an integer from 1 to 100; R1, R2, R3 and R4 are H, C1-C32 alkyl, phenyl and alkylbenzene or alkoxy benzene containing one or more C1-C32; and M is a metal ion. The metalloporphyrin-thienothiadiazole organic semiconductor material has good film-forming property, strong absorbance and wide light absorption range, thus improving the sunlight use ratio of the material. The material also has better heat stability and environmental stability. Besides, the preparation method is simple in process and easy to operate and control.

Description

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

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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