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A kind of star conjugated structure polymer and its preparation method and application

A conjugated structure and polymer technology, applied in the field of star-shaped conjugated structure polymers and their preparation, can solve the problems of low electrical performance of field effect transistor devices, and achieve good application prospects, simple synthesis routes, and strong practicability. Effect

Active Publication Date: 2021-05-07
杭州奥得科技有限公司
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  • Description
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Problems solved by technology

Patent CN102844312B discloses a polymer of benzodithiophene and its use as an organic semiconductor. However, the polymer of this patent is a linear polymer, and there are certain problems in solubility; Star-based silicon-containing polymer and its preparation method and application, although the solubility is improved, but the electrical performance of the field effect transistor device prepared by the polymer is relatively low

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  • A kind of star conjugated structure polymer and its preparation method and application
  • A kind of star conjugated structure polymer and its preparation method and application
  • A kind of star conjugated structure polymer and its preparation method and application

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preparation example Construction

[0041] Another object of the present invention is to provide the preparation method of above-mentioned polymer, comprises the following steps:

[0042] Step S1, under anhydrous and oxygen-free conditions, reflux reaction of 2,5-diamino-1,4-benzenedithiol dihydrochloride and 3-RS-2-thiophenecarbaldehyde under piperidine conditions, One-step method to obtain 2,2'-bis-(3-RS-thiophene)-benzobithiazole;

[0043] Step S2, reacting the 2,2'-bis-(3-RS-thiophene)-benzobithiazole obtained in step S1 with butyllithium (1.6M) at -78°C under anhydrous and oxygen-free conditions , to obtain a lithium compound, and then react with trimethyltin chloride to obtain a bistin-substituted 2,2'-bis-(3-RS-thiophene)-benzobithiazole as a polymerization precursor ①;

[0044] Step S3, combining the bistin-substituted 2,2'-bis-(3-RS-thiophene)-benzobithiazole and tribromotrithienoacene and / or tribromotrithiophene obtained in step S2 Biphenyl (polymerization precursor 2.) carries out Stille coupling re...

Embodiment 1

[0057] Embodiment 1, the synthesis of 2,2'-two-(3-dodecylthio-thiophene)-benzobithiazole

[0058] In a 100mL round bottom flask, add 3-dodecylthio-2-thiophenecarbaldehyde (50mmol, 14.0g) and 2,5-diamino-1,4-benzenedithiol dihydrochloride (20mmol, 2.8 g), add 50mL of anhydrous tetrahydrofuran after filling with nitrogen, then add 10mL of piperidine, heat and reflux for 24 hours, cool to room temperature, pour into water, filter the precipitated solid, wash with water, and wash with methanol. The obtained crude product was purified by silica gel column, petroleum ether: ethyl acetate was used as eluent, and the solvent was spin-dried to obtain brown yellow solid 2,2'-bis-(3-dodecyl-thiophene)-benzobis Thiazole, the yield was 48.6%.

[0059] The brownish yellow solid was detected by mass spectrometry and nuclear magnetic resonance: MS (Maldi-TOF) m / z: 756 (M+); 1 H NMR (400MHz, CD 2 Cl 2 ppm): δ=8.20(s,2H), 7.18(d,2H), 6.68(d,2H), 2.57(t,24H), 1.63(m,4H), 1.34-1.26(m,36H), 0...

Embodiment 2

[0060] Example 2, the synthesis of 2,2'-two-(3-dodecylsulfanyl-5-(trimethyltin)-thiophene)-benzobithiazole

[0061] In a 250mL three-necked flask, add 2,2'-bis-(3-dodecylthio-thiophene)-benzobithiazole (5mmol, 3.78g) under a nitrogen atmosphere, add 80mL of dry tetrahydrofuran, and Slowly add butyl lithium (12mmol, 2.5M, 4.8mL) dropwise, continue to stir for 1 hour, add trimethyltin chloride (14mmol, 1M, 14mL), gradually rise to room temperature and react overnight, add saturated ammonium chloride solution, Extract with ether, wash with water, combine the organic phases, dry over anhydrous magnesium sulfate, filter and spin off the solvent. The obtained crude product was purified by a neutral alumina column, petroleum ether: ethyl acetate was used as eluent, and the solvent was spin-dried to obtain a light yellow solid 2,2'-bis-(3-dodecylthio-5- (Trimethyltin)-thiophene)-benzobithiazole, the yield was 62.6%.

[0062] The light yellow solid was detected by mass spectrometry, ...

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Abstract

The present invention uses benzobithiazole, trithienoacene and trithiophene biphenyl as copolymerization structural units, and obtains a star-shaped conjugated structure polymer through chemical copolymerization, and the polymer utilizes the higher electron affinity of benzobithiazole , can reduce the energy level of the lowest unoccupied orbital of the polymer, the introduction of the alkylthio group can not only improve the solubility of the compound, but also improve the stability of the compound. Trithienoacene has good planarity and conjugation, and can be simultaneously Adjusting the energy level, solubility and electrical properties of materials has good application prospects in organic photoelectric devices such as organic solar cells, organic field effect transistors and organic light-emitting diodes, as well as organic thermoelectric devices. It has strong practicability and strong promotion and application value. .

Description

【Technical field】 [0001] The invention belongs to the technical field of chemical production, and in particular relates to a polymer with a star-shaped conjugated structure and a preparation method and application thereof. 【Background technique】 [0002] Compared with inorganic semiconductors, organic semiconductors have obvious advantages. Not only can the structure be tailored and the performance can be adjusted, but also it has the characteristics of low cost, low processing temperature, solution processability, and flexibility. Organic semiconductors can be between insulators and semiconductors in terms of conductivity. The research on organic semiconductors mainly focuses on the research of materials and devices, among which organic field effect transistors (Organic Field Effect Transistors, OFETs), organic light-emitting diodes (Organic Light-Emitting Diode, OLED), organic solar photovoltaic cells (Organic Photovoltaic cells) Voltaic SolarCell, OPV) and other fields h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12
CPCC08G61/126C08G2261/124C08G2261/145C08G2261/18C08G2261/3223C08G2261/3243C08G2261/3246C08G2261/414C08G2261/95
Inventor 高建华
Owner 杭州奥得科技有限公司
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