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

A technology of organic semiconductors and metalloporphyrins, 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 and Environmental stability, good electronic buffering and optoelectronic magnetism, effect of expanding 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-anthracene organic semiconductor materials containing silfluorene, which greatly limits the application range of organic semiconductor materials.

Method used

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

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preparation example Construction

[0050] The preparation method of metalloporphyrin-anthracene organic semiconductor material designed by the present invention, the steps are as follows:

[0051] In step S1, under the condition that the oxidizing agent and the first catalyst exist, the structural formula is The dipyrromethane, the structural formula is The first silafluorene derivative and the structural formula are The second silfluorene derivative is dissolved in the first organic solvent, and reacted for 1-24 hours at a temperature of 20-100° C. to obtain the structural formula: The silicon fluorene porphyrin derivatives; 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:

[0052]

[0053] Step S2, adding the silicon fluorene porphyrin derivative and brominating agent obtained in step S1 into the second organic solvent, and reacting at 0-120° C. for 1-72 hours to obtain the...

Embodiment 1

[0079] This embodiment discloses a silicon fluorene zinc porphyrin-anthracene organic semiconductor material with the following structure

[0080]

[0081] In the above formula, n=78;

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

[0083] 1. Synthesis of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) anthracene

[0084]

[0085] in N 2 Under the protection of the three-necked flask, add 10 g of p-9,10-dibromoanthracene, add 250 ml of tetrahydrofuran (THF, the same below) solvent, and slowly inject n-butyllithium (n- BuLi, the same below) 25.2mL (2.5M), continue to stir the reaction for 2 hours, inject 2-isopropoxy-4,4,5,5-tetramethyl-1,3 with a syringe at -78°C, 13 mL of 2-dioxaborane was stirred overnight at room temperature. The reaction was terminated by adding saturated aqueous sodium chloride solution, extracted with chloroform, dried over anhydrous sodium sulfate, and the filtrate was collected after suc...

Embodiment 2

[0104] This embodiment discloses a silicon fluorene iron porphyrin-anthracene organic semiconductor material with the following structure

[0105]

[0106] In the above formula, n=56;

[0107] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0108] 1. Synthesis of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) anthracene

[0109] Its preparation sees embodiment 1 for details.

[0110] 2. Synthesis of 5-(9'-methyl-9'-hexadecyl)silafluorene-15-(9'-docosyl)silafluorene porphyrin

[0111]

[0112] 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 a...

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Abstract

The invention belongs to the field of photoelectron materials, which discloses a metal porphyrin-anthracene organic semiconductor material as well as a preparation method and application thereof. The metal porphyrin-anthracene organic semiconductor material has a structural formula (I), wherein n is an integer from 1-100, R1, R2, R3 and R4 is H, the alkyl of C1-C32, phenyl and alkylbenzene or alkoxy benzene containing one or a plurality of C1-C32 respectively, and M is a metal ion. The metal porphyrin-anthracene organic semiconductor material provided by the invention has the advantages of good film forming property, high current carrier migration rate, strong absorbance and wide light absorption range, and the use ratio of the porphyrin-anthracene organic semiconductor material on sunlight is improved. 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, in particular to a metalloporphyrin-anthracene organic semiconductor material. [0002] The invention also relates to the preparation method and application of the metal porphyrin-anthracene 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 eff...

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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