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Thiophene organic semiconductor material and preparation method and application thereof

An organic semiconductor and thiophene technology, applied in the field of organic semiconductor materials, can solve the problems of low conversion efficiency of inorganic solar cells, low collection efficiency of carrier electrodes, and ineffective use of the red light region, achieving excellent electrochemical reduction properties, The effect of high electron transport properties and good environmental stability

Active Publication Date: 2012-03-14
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

At present, the research on polymer solar cells mainly focuses on the blending system of donor and acceptor, using PTB7 and PC 71 The energy conversion efficiency of the BM blend system has reached about 7%, but it is still much lower than that of inorganic solar cells.
The main constraints limiting performance improvements are: relatively low carrier mobility of organic semiconductor devices, mismatch of the spectral response of the device with the solar radiation spectrum, inefficient use of the red region of high photon flux, and the lack of carrier mobility. Electrode collection efficiency is low, etc.

Method used

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  • Thiophene organic semiconductor material and preparation method and application thereof
  • Thiophene organic semiconductor material and preparation method and application thereof
  • Thiophene organic semiconductor material and preparation method and application thereof

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Experimental program
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Effect test

preparation example Construction

[0042] The present invention also provides a method for preparing a class of thiophene organic semiconductor materials, comprising the following steps:

[0043] Step S1, the preparation of 5,8-dibromo-2,3-disubstituted-quinoxaline

[0044] Mix and react 3,6-dibromo-o-phenylenediamine and alkyl ethylene dione to obtain 5,8-dibromo-2,3-disubstituted-quinoxaline; the reaction formula is as follows:

[0045]

[0046] Step S2, the preparation of 5,8-bis-(4-alkyl-2-thienyl)-2,3-disubstituted-quinoxaline

[0047] In an oxygen-free environment, the 5,8-dibromo-2,3-disubstituted-quinoxaline, 3-alkyl-2-boronic acid thiophene and anhydrous sodium carbonate were added to the second organic compound containing the second catalyst. In a solvent, the reaction produces 5,8-bis-(4-alkyl-2-thienyl)-2,3-disubstituted-quinoxaline; wherein, the second catalyst is organic palladium or organic palladium and organic palladium A mixture of phosphorus ligands; the second organic solvent is at leas...

Embodiment 1

[0066] Embodiment 1 The structural formula of a class of thiophene organic semiconductor materials in this embodiment is as follows:

[0067]

[0068] In the formula, R 1 , R 4 , R 2 , R 3 for C 1 -C 20 The alkyl group; Its preparation process is as follows:

[0069] 1. 5,8-di-(5-bromo-4-substituted-2-thienyl)-2,3-dialkyl-quinoxaline, the structural formula is as follows:

[0070]

[0071] Now take 5,8-bis-(5-bromo-2-(4-dodecyl)thienyl)-2,3-dioctyl-quinoxaline as an example for illustration.

[0072] 1), 5,8-dibromo 2,3-dioctyl-quinoxaline, the structural formula is as follows:

[0073]

[0074] Take the preparation of 5,8-dibromo-2,3-dioctylquinoxaline as an example to illustrate, and the preparation process is as follows:

[0075]

[0076] 3,6-Dibromo-o-phenylenediamine (0.5 g, 1.85 mmol) was added to a solution of the compound dioctylethylenedione (0.28 g, 1 mmol) in acetic acid (30 mL) at 120°C. Reflux overnight, pour the reaction solution into water, ...

Embodiment 2

[0114] Embodiment 2 The structural formula of a class of thiophene organic semiconductor materials in this embodiment is as follows:

[0115]

[0116] In the formula, R 1 , R 4 is an alkyl group, R 2 , R 3 for C 1 -C 20 Alkyl substituted phenyl; Its preparation process is as follows:

[0117] 1. 5,8-bis-(5-bromo-2-thienyl)-2,3-diphenyl-quinoxaline

[0118]

[0119] The preparation of 5,8-bis-(5-bromo-4-n-eicosyl-2-thienyl)-2,3-diphenyl-quinoxaline will now be described as an example. The preparation process is as follows:

[0120]

[0121] Under nitrogen atmosphere, NBS (0.6g, 3.3mmol) was added to 5,8-di(4-n-dodecyl-2-thienyl)-2,3-dioctyl-quinoxaline (1.2 g, 1.53mmol) in tetrahydrofuran (THF 50mL) and stirred overnight at room temperature. The reaction solution was spin-dried and the crude product was obtained by column chromatography with a yield of 73%. MS (MALDI) m / z: 941 (M + )

[0122] Among them, the preparation of 4,4-dialkyl-2,6-bistrimethyltin-cy...

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Abstract

The invention belongs to the field of photoelectronic materials, and discloses a thiophene organic semiconductor material and a preparation method and application thereof. The copolymer has a general formula (P), wherein in the formula, x+y is equal to 2; x is more than or equal to 1, and y is more than 0 and is less than 1; n is more than 1 and is less than or equal to 100; R1 and R4 are alkyl having 1 to 20 carbon atoms; and R2 and R3 are hydrogen and alkyl having 1 to 20 carbon atoms or phenyl substituted by alkyl having 1 to 20 carbon atoms or alkoxy having 1 to 20 carbon atoms or are thephenyl. Compared with the prior art, the invention has the advantages that: the organic semiconductor material is prepared by polymerizing a cyclopentadiene [2,1-b:3,4-b'] bithiophene unit, a thiophene unit and a quinoxaline unit, so the carrier mobility of the organic semiconductor material is increased, spectral response is broadened, and the organic semiconductor material has high carrier transmission property and electrochemical property; and the alkyl and the like can be introduced by a simple and convenient method to improve solubility. The preparation process of the semiconductor material is simple and easy to operate and control, and is suitable for industrial production.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to a class of thiophene organic semiconductor materials. The invention also relates to a preparation method and application of a class of thiophene organic semiconductor materials. Background technique [0002] 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. Silicon solar cells currently used on the ground are limited in application due to complex production processes and high costs. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. If the energy conversion efficiency can be imp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/30H01L51/46H01L51/54H01S5/36
CPCY02E10/549
Inventor 周明杰黄杰许二建
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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