Polymer containing DPP, thiophene and fluorothiophene structural units as well as preparation method and application of polymer

A technology of structural units and polymers, which is applied in the fields of electrical components, semiconductor/solid-state device manufacturing, and photovoltaic power generation. It can solve the problems of complex synthesis routes and raw materials, which need to be improved, and achieve strong promotion and application value, and a large molar absorptivity coefficient. , Optimize the effect of energy level

Inactive Publication Date: 2020-05-05
杭州奥得科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The light absorption, solubility and electrical properties of existing organic polymer materials need to be improved, and the synthesis route and raw materials are relatively complicated
Patent CN102844312B discloses a polymer of benzodithiophene and its use as an organic semiconductor, but there are certain problems in the solubility of the patent; therefore, further development of new organic polymers with superior light absorption, solubility and electrical properties And improving its preparation process has become the focus of current research and development

Method used

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  • Polymer containing DPP, thiophene and fluorothiophene structural units as well as preparation method and application of polymer
  • Polymer containing DPP, thiophene and fluorothiophene structural units as well as preparation method and application of polymer
  • Polymer containing DPP, thiophene and fluorothiophene structural units as well as preparation method and application of polymer

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Experimental program
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preparation example Construction

[0039] A preparation method of a polymer containing DPP, thiophene and fluorothiophene structural units, comprising the following steps:

[0040] Provide 2,5-dibromothiophene, 2,5-dibromo-3,4 difluorothiophene and compound DPP, the structural formula of compound DPP is:

[0041]

[0042] Among them, R is C 6 ~C 16 the alkyl group;

[0043] Under nitrogen protection conditions, according to the number of parts of the substance, (1.0 to 1.5) parts of compound R-DPP, a part of 2,5-dibromothiophene and b part of 2,5-dibromo-3,4 difluoro Add thiophene to an organic solvent, add a catalyst, and carry out a stille coupling reaction at 100°C to 130°C for 3 to 7 days; after separation and purification, a polymer containing DPP, thiophene and fluorothiophene structural units is obtained, and the DPP-containing The polymer of , thiophene and fluorothiophene structural unit is the polymer P with following general formula:

[0044]

[0045] Among them, 06 ~C 16 alkyl; n is an in...

Embodiment 1

[0056] Embodiment 1 2,5-dibromo-3, the synthesis of 4 difluorothiophene

[0057] Add LDA (273mmol) into a three-necked flask containing 150mL of anhydrous tetrahydrofuran to dissolve; after the solution is cooled to -78°C, slowly add nBuLi (273mmol), followed by 2,5-dibromothiophene (124mmol), The reaction was stirred for 2 h to obtain a yellow solution; after the reaction was completed, chlorotrimethylsilane (300 mmol) was added to the yellow solution within 1 h, then heated to room temperature and stirred overnight; the aqueous layer was removed with diethyl ether (100 mL), and the organic phase was It was dried over sodium sulfate, concentrated by filtration under reduced pressure, and vacuum distilled to obtain 3,4-dibromo-2,5-bis(trimethylsilyl)-thiophene with a yield of 90%.

[0058] Dissolve 3,4-dibromo-2,5-bis(trimethylsilyl)-thiophene (18mmol) in 80mL of anhydrous tetrahydrofuran, and after cooling to -78°C, add nBuLi (35mmol) and N-fluoro-N -(Benzenesulfonyl)benzene...

Embodiment 2

[0063] The synthesis of embodiment 2 polymer P1

[0064] 2,5-dibromothiophene (0.1mmol), 2,5-dibromo-3,4 difluorothiophene (0.1mmol) and compound C 6 h 13 -DPP (0.2mmol) was added to a 50ml flask, pumped and filled with nitrogen for 3 times, quickly added bistriphenylphosphine palladium dichloride (0.008mmol) catalyst in the state of bulging, and pumped and ventilated 3 times , add toluene solvent (40ml) and sodium carbonate (5ml), then the flask is heated to 120 ℃ to carry out Still coupling reaction 5 days, then cools down to stop polymerization reaction, then pours methanol (90ml) into the flask and settles, filters, and then Extracted with methanol and n-hexane for 24 hours, and finally extracted with chloroform, spin-dried, vacuum pumped and filtered overnight to obtain polymer P1 with a yield of 56%.

[0065] The specific synthetic route of polymer P1 is:

[0066]

[0067] After detection, the product polymer P1 Mn: 50.2kDa, PDI: 2.13.

[0068] The application of ...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a polymer containing DPP, thiophene and fluorothiophene structural units and a preparation method and application ofthe polymer. R in the three-component polymer is alkyl, the number of carbon atoms is 6-16, n is a natural number ranging from 1 to 100, and x is larger than 0 and smaller than 1. By adjusting the ratio of thiophene to fluorothiophene, the photoelectric material with excellent performance is obtained. Repetitive units in the polymer can enhance charge transfer in a compound and improve the sunlight capture capability and hole transport capability. The preparation method is simple and controllable, and has a good application prospect in the photoelectric fields of solar cell devices, organic electroluminescent devices, organic field effect transistors and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a polymer containing DPP, thiophene and fluorothiophene structural units, a preparation method and application thereof. Background technique [0002] In recent years, organic optoelectronic functional materials with high mobility have attracted extensive attention as an important part of organic integrated devices. Organic field-effect transistors are expected to replace traditional silicon-based field-effect transistors in many application fields due to their advantages of low cost, easy modulation and simple process, and have more potential application prospects in flexible devices such as wearable devices. As the core component of organic field effect transistors, organic semiconductor materials play a key role in the properties of devices. Therefore, the design and synthesis of high-performance organic semiconductor materials and functional materials have become th...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46H01L51/54
CPCC08G61/126C08G61/124C08G2261/122C08G2261/1412C08G2261/146C08G2261/3223C08G2261/3241C08G2261/354C08G2261/414C08G2261/514C08G2261/91C08G2261/95C08G2261/92H10K85/113H10K85/151Y02E10/549
Inventor 高立群刘江涛乔冠伟高建华马望京
Owner 杭州奥得科技有限公司
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