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Diselenophenobenzodiindene conjugated polymer semiconductor materials and their applications

A technology of conjugated polymers and benzobisindene derivatives, which can be used in semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve problems such as limited mobility, and achieve improved photovoltaic performance and high hole mobility. , the effect of improving the mobility

Inactive Publication Date: 2015-09-30
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the mobility of TPT-containing polymers is still limited, and the absorption performance needs to be further improved.

Method used

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  • Diselenophenobenzodiindene conjugated polymer semiconductor materials and their applications
  • Diselenophenobenzodiindene conjugated polymer semiconductor materials and their applications
  • Diselenophenobenzodiindene conjugated polymer semiconductor materials and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] When R is a 2-ethylhexyl chain, the monomer M can be expressed as the monomer M 1 , with the following structure:

[0025]

[0026] The monomer M of the embodiment of the present invention 1 The synthetic route of is as follows:

[0027]

[0028] Compound 1

[0029] Add 16.2g of 2,5-dibromoterephthalic acid (50mmol) and 40ml of thionyl chloride (SOCl 2 ) was heated to reflux for 12h, and when the solution became clear, SOCl was removed by atmospheric distillation 2 , adding petroleum ether, cooling to precipitate a solid, and suction filtration to obtain 17.1 g of compound 1 with a yield of 95%. 1 H-NMR (400MHz, CDCl 3 , δppm): 8.21 (s, 2H).

[0030] Compound 2

[0031] Under ice bath, to 200ml CH containing 7.2g (20mmol) compound 1 2 Cl 2 Slowly add 6.8g of crushed AlCl to the solution 3 (51mmol) powder, to be AlCl 3 After dissolution, 25 ml of CH containing 15.6 g of 2-ethylhexylbenzene (82 mmol) was added 2 Cl 2 solution. Stir at room temperature an...

Embodiment 2

[0041] The structural formula and synthetic route of the conjugated polymer material P(SePSe-2,4-BT) of the embodiment of the present invention are as follows:

[0042]

[0043] N 2 Under the protection of , add 0.504g (0.35mmol) of monomer M in a 50ml single-necked bottle 1 And 0.103g (0.35mmol) monomer a and 20mg tetrakis (triphenylphosphine) palladium [abbreviated as Pd (PPh 3 ) 4 ], add 20ml of anhydrous toluene, after heating to reflux for 48h, the reaction mixture is poured into methanol (500mL) for coagulation, the precipitation is filtered to obtain the first product, and the first product is extracted with methanol, acetone, and n-hexane respectively with a Soxhlet extractor. After extracting for 24 hours, the soluble part was collected with chloroform and vacuum-dried to obtain 340 mg of polymer material P(SePSe-2,4-BT), with a yield of 78%. 1 H-NMR (400MHz, CDCl 3 , δppm): 8.2-7.9 (br, 2H), 7.9-7.6 (br, 2H), 7.6-7.4 (br, 2H), 7.4-7.2 (br, 8H), 7.1-6.9 (br, 8H...

Embodiment 3

[0046] The structural formula and synthetic route of the conjugated polymer material P(SePSe-2,4-DTDPP) of the embodiment of the present invention are as follows:

[0047]

[0048] N 2 Under protection, 0.432g (0.3mmol) of monomer M 1 and 0.272g (0.3mmol) of monomer b and 17mg of Pd (PPh 3 ) 4 Dissolve in 20ml of anhydrous toluene, heat and reflux for 48h, pour the reaction mixture into methanol (500mL) for coagulation and precipitation, the precipitate is filtered to obtain the primary product, and the primary product is extracted with methanol, acetone, and n-hexane with a Soxhlet extractor, respectively. After extracting for 24 hours, the soluble part was collected with chloroform and vacuum-dried to obtain 470 mg of polymer material P(SePSe-2,4-DTDPP), with a yield of 84%. 1 H-NMR (400MHz, CDCl 3 , δppm): 9.0-8.7 (br, 2H), 7.5-7.3 (br, 4H), 7.3-7.1 (br, 10H), 7.1-6.9 (br, 8H), 4.2-3.8 (br, 4H), 2.75 -2.25(br, 8H), 2.1-1.8(br, 2H), 1.7-1.5(br, 4H), 1.5-1.0(br, 80H),...

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Abstract

The invention belongs to the field of organic semiconductor material, and specifically relates to a diseleno indacene conjugated polymer semiconductor material and an application thereof in optoelectronic devices. The material has a structure represented by a general formula I. R is H, C1-C20 alkyl or alkoxy, n is polymerization degree and is any integer of 2-100. The invention further provides the application of the conjugated polymer material in organic solar cell devices, organic photovoltaic materials, organic field effect transistor devices, organic electroluminescent devices, organic optical memory devices, and organic laser devices. The conjugated polymer material has the advantages of controllable energy level structure, adjustable band gap, wide range of spectral absorption, and high hole mobility.

Description

technical field [0001] The invention belongs to the field of organic semiconductor materials, and in particular relates to a diselenophenobenzodiindene conjugated polymer semiconductor material and its application in photoelectric devices. Background technique [0002] The development of organic semiconductor materials with excellent photoelectric properties for the construction of low-cost optoelectronic devices is a very important development direction in recent years. These organic semiconductor materials can be widely used in optoelectronic devices such as organic field-effect transistors, organic light-emitting diodes, photodetectors, organic solar cells, sensors, memory elements, and logic circuits. Among them, organic solar cells are currently a hot area of ​​concern. [0003] Compared with inorganic solar cells, organic solar cells have the advantages of flexibility, light weight, low cost, and easy large-area processing. However, the low photoelectric conversion e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 肖生强蒋尊龙詹春芦露华
Owner WUHAN UNIV OF TECH
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