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Novel conductive polymer and preparation method and application thereof

A conductive polymer and polymer technology, applied in the field of new conductive polymers and their preparation, can solve problems such as difficulty in preparation, difficult synthesis routes, and poor solubility, and achieve solubility optimization, strong promotion and application value, and improved solubility Effect

Inactive Publication Date: 2021-02-19
SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Factors such as poor stability, low mobility, and difficult synthesis routes make OFET materials far from the goal of industrialization
Among them, the disadvantage of poor solubility makes it difficult for OFET materials to use low-cost solution methods to prepare transistor devices.

Method used

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  • Novel conductive polymer and preparation method and application thereof
  • Novel conductive polymer and preparation method and application thereof
  • Novel conductive polymer and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0039] On the other hand, the embodiment of the present application also provides a preparation method of a novel conductive polymer, comprising the following steps:

[0040] 3,6-bis(bromodithiophen-2-yl)-2,5-diRpyrrole[3,4-c]pyrrole-1,4-dione and bistanno(E)-1, 2-bis(3-R'-thiophen-2-yl)ethylene is added to the organic solvent to obtain a mixed solution;

[0041] A catalyst is added to the mixed solution, and the mixed solution is subjected to a Stille coupling reaction at a set reaction temperature and a set reaction time to obtain the polymer.

[0042] In the examples of the present application, the 3,6-bis(bromodithiophen-2-yl)-2,5-diR pyrrole[3,4-c]pyrrole-1,4-dione has the following formula II structure:

[0043]

[0044]The bistin generation (E)-1,2-bis(3-R'-thiophen-2-yl)ethylene has the following structure of formula III:

[0045]

[0046] Wherein, the R' is a sulfanyl group and / or an oxyalkyl group, and the number of carbon atoms of the R' is 6-16.

[0047] ...

Embodiment 1

[0056] Example 1: Synthesis of (E)-1,2-two (3-bromo-2-thiophene) ethylene

[0057] See figure 1 , figure 1 It is a synthetic route diagram of (E)-1,2-bis(3-bromo-2-thiophene) ethylene (TVT) in the embodiment of the application, and the E)-1,2-bis(3 The specific preparation process of -bromo-2-thiophene) base ethylene is as follows:

[0058] At 0°C, under anhydrous and oxygen-free conditions, add 3-bromothiophene (100mmol), dry THF (100ml) and strong base LDA (120mmol) into the flask, react for 1h, then add dry DMF (120mmol), and react 0.5h, after the reaction was finished, it was lowered to room temperature, overnight, after-treatment to obtain a brown liquid, which was the intermediate product 4-bromothiophene-2-carbaldehyde, and the yield was 52%; the above-mentioned brown liquid was detected by nuclear magnetic resonance: 1H NMR (300MHz , d-DMSO ppm): δ=7.28 (s, H), 7.37 (s, H), 9.41 (s, H).

[0059] TiCl4 (20mmol) was added dropwise to a flask equipped with dry THF (30...

Embodiment 2

[0060] Example 2: Synthesis of Polymer P1

[0061] A preparation method of a novel conductive polymer, the polymer P1 has the following general formula:

[0062]

[0063] The method comprises the following steps: 3,6-bis(dithiophen-2-yl)-2,5-dihydropyrrole[3,4-c]pyrrole-1,4-dione (BT-DPP)( 200mmol), K2CO3 (8.0mmol), DMF (1000ml) were added to a 5L three-necked flask, replaced with nitrogen twice, the temperature was raised to 120°C, the phase transfer catalyst 18-crown-6 was added, and 9-(bromomethylene) was added dropwise Nonadecane (600mmol), after dropping, heated up to 130°C, reacted for 48h, after the end, cooled down to room temperature, extracted, separated, dried to obtain 2,5-bis(2-octyldodecyl)- BT-DPP. Add the obtained 2,5-bis(2-octyldodecyl)-BT-DPP (80mmol), NBS (80mmol), and DCM (dry 400ml) into a 700mL three-necked flask, and replace it with nitrogen twice. Temperature 15℃~20℃, react for 37h, after the reaction, hydrolyze, wash with water, and dry to obtain...

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Abstract

The invention provides a novel conductive polymer as well as a preparation method and an application thereof, and the novel conductive polymer is a polymer with a structure as shown in the following formula I, wherein R is C6-C18 alkyl; R'is a sulfanyl group or an oxyalkyl group of C6-C16; and n is an integer between 1 and 100. According to the polymer, on the basis of introduction of a thiophenecompound, flexible alkyl chain modification is further carried out on the structure of the thiophene compound, and a C=C bond is introduced, so that the solubility of the polymer is greatly improved,and the molecular mobility can be well improved; meanwhile, by introducing a bithiophene (BT) and sulfanyl oxyalkyl structure, the energy level, solubility, electrical properties and the like of the material can be optimized, so that the polymer has the advantages of excellent performance, good light absorption, high thermal stability and the like.

Description

technical field [0001] The application relates to the technical field of organic synthesis, in particular to a new conductive polymer containing DPP-dithiophene and 1,2-bis(thiophen-2-yl)ethylene structural units and its preparation method and application. Background technique [0002] Since the beginning of the 21st century, with the improvement of human's demand for electronic technology, various high-tech products have emerged, among which organic photoelectric functional materials and devices have developed rapidly in this process. Organic photoelectric functional materials have photoelectric activity and can realize photoelectric conversion under the action of external fields (light, magnetism, heat, electricity, etc.), so they are widely used in many fields such as organic transistors, organic solar cells, and organic light-emitting diodes. Among them, Organic Field Effect Transistors (OFETs) are widely used in flexible devices such as wearable devices due to their adv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/126C08G2261/124C08G2261/414C08G2261/1412C08G2261/145C08G2261/1424C08G2261/1428C08G2261/3241C08G2261/3243C08G2261/3327C08G2261/91C08G2261/5222C08G2261/51
Inventor 宋健李铁
Owner SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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