Organic semiconductor material containing fluorene, anthracene and thienothiophene units, preparation method and application thereof

A technology of organic semiconductors and thiophene units, which is applied in the field of preparation and organic semiconductor materials, can solve the problems of low photoelectric conversion efficiency of organic solar cells, achieve excellent charge transport performance, improve transport speed and efficiency, and facilitate film-forming processing

Inactive Publication Date: 2011-12-21
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

[0003] The technical problem to be solved by the present invention is to provide an organic sola...

Method used

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  • Organic semiconductor material containing fluorene, anthracene and thienothiophene units, preparation method and application thereof
  • Organic semiconductor material containing fluorene, anthracene and thienothiophene units, preparation method and application thereof
  • Organic semiconductor material containing fluorene, anthracene and thienothiophene units, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 This example discloses polymers P1 and P2 with the following structures, wherein n=10 in polymer P1 and n=45 in polymer P2:

[0038]

[0039] Polymer P1 x=0.1, y=0.9

[0040] P2 x=0.5, y=0.5

[0041] The preparation steps of P1 and P2 are as follows:

[0042] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dioctylfluorene:

[0043]

[0044] Tetrahydrofuran refining: add tetrahydrofuran solvent that has been dried with KOH for several days into a 1000ml single-necked bottle, then cut into sodium block and add benzophenone, keep stirring and reflux until the system turns dark purple, distill out the refined THF for later use.

[0045] Set up an anhydrous and anaerobic reaction device, stirring and N 2 Under the protection of the three-necked flask, add 9.0mmol of white 2,7-dibromo-9,9-dioctylfluorene, inject 150ml of the above-mentioned refined tetrahydrofuran solvent with a syringe, and then use a syringe to slowly Inj...

Embodiment 2

[0055] Example 2 This example discloses polymers P3 and P4 with the following structures, wherein n=13 in polymer P3 and n=18 in polymer P4:

[0056]

[0057] Polymer P3 x=0.8, y=0.2

[0058] P4 x=0.2, y=0.8

[0059] The preparation steps of P3 and P4 are as follows:

[0060] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dioctylfluorene:

[0061] For the preparation process, see Step 1 in Example 1.

[0062] Step 2, preparation of P3 and P4:

[0063]

[0064] Polymer P3 x=0.8, y=0.2

[0065] P4 x=0.2, y=0.8

[0066] Add 1mmol 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dioctylfluorene, 0.8mmol 9,10-dibromo-2,6-bis(2-octyldecyl)anthracene (see Klaus Mullen et al. Macromol.Chem.Phys.2006, 207, 1107-1115 for the synthesis method of this compound), 0.2mmol2, 5-dibromothieno[3,2-b]thiophene, 0.02mmol tetrakistriphenylphosphine palladium, 10ml Na with a concentration of 2mol / L 2 CO 3 Aqueous solution and 40ml toluene s...

Embodiment 3

[0070] Example 3 This example discloses polymers P5 and P6 with the following structures, wherein n=20 in polymer P5 and n=28 in polymer P6:

[0071]

[0072] Polymer P5 x=0.2, y=0.8

[0073] P6 x=0.5, y=0.5

[0074] The preparation steps of P5 and P6 are as follows:

[0075] Step 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dioctylfluorene:

[0076] For the preparation process, see Step 1 in Example 1.

[0077] Step 2, preparation of P5 and P6:

[0078]

[0079] Polymer P5 x=0.2, y=0.8

[0080] P6 x=0.5, y=0.5

[0081] Add 1mmol 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dioctylfluorene, 0.2mmol 9,10-dibromo-2,6-bis(2-octyldecyl)anthracene, 0.8mmol 3,6-dihexyl-2,5-dibromothieno[3,2-b]thiophene (the compound The synthesis of see document He, Y.; Wu, W.; Macromolecules 2008,41,9760 of Zhao, G. etc.), 0.022mmol tetrakistriphenylphosphine palladium, 10ml concentration is the Na of 2mol / L 2 CO 3 Aqueous solution and 40ml t...

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Abstract

The invention discloses an organic semiconductor material containing fluorene, anthracene and thiophene bithiophene, a preparation method thereof and an application thereof. The organic semiconductor material is a substance with the following general formula: the preparation method comprises the following steps of: reacting 2,7-dibromo-9,9-dialkyl fluoryl, n-butyllithium and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxolane borane or bis(pinacolato)diboron to obtain an intermediate product at -70 to -85 DEG C under the condition without water and oxygen; and (2) carrying out Suzuki reaction onthe intermediate product and 9,10-dibromoanthracene or derivative as well as thieno[3,2-b] thiophene or derivative under the condition without oxygen so as to obtain the final product. The product has the advantages of good light and heat stability, good film forming property and high photoelectric conversion efficiency. The preparation method has the advantages of simple route and low technical requirement. The material disclosed by the invention is applied to the aspects like organic solar cell devices, organic field effect transistors, organic electroluminescent devices and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to a polymer, a preparation method and its application, and more specifically relates to an organic semiconductor material containing fluorene, anthracene and thienothiophene units, a preparation method and its application. Organic semiconductor materials containing fluorene, anthracene and thienothiophene units are specifically applied in the fields of organic solar cells, organic field effect transistors, organic electroluminescence, organic optical storage, organic nonlinear materials and organic lasers. Background technique [0002] At present, high-efficiency solar cells are usually silicon solar cells made of inorganic semiconductors. However, due to the complex production process, serious pollution, high energy consumption, and high cost of silicon solar cells, the development of commercial applications has been inhibited. Organic solar cells are a new type of solar c...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/00H01S5/36
Inventor 周明杰黄杰黄佳乐
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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