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Triphenylamine polymers containing oligoether side chains and their application in solution-based preparation of organic optoelectronic devices

A technology of triphenylamine and oligopolyether, which is applied to triphenylamine polymers and its application field in the preparation of organic optoelectronic devices by solution method, can solve the problems of solvent erosion, large material loss and high energy consumption of the active layer, and achieves high efficiency. Effect of hole mobility, ease of synthesis, high hole transport ability

Active Publication Date: 2019-10-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional triphenylamine-based P-type materials are mostly processed by evaporation, and evaporation-type materials have disadvantages such as easy crystallization, large material loss, and high energy consumption.
A small number of solution-processed triphenylamine P-type materials are only processed with weak polar solvents such as toluene and chlorobenzene, which is related to the problem of solvent erosion in the active layer.

Method used

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  • Triphenylamine polymers containing oligoether side chains and their application in solution-based preparation of organic optoelectronic devices
  • Triphenylamine polymers containing oligoether side chains and their application in solution-based preparation of organic optoelectronic devices
  • Triphenylamine polymers containing oligoether side chains and their application in solution-based preparation of organic optoelectronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 4,4'-dibromo-4"(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-triphenylamine (2)

[0030]

[0031] (1) Synthesis of 4,4'-dibromo-4"-hydroxytriphenylamine (1): Under nitrogen protection, 4,4'-dibromo-4"-methoxytriphenylamine (4.33g, 10mmol) Dissolved in 50ml of anhydrous dichloromethane, then slowly dropwise added in the solution of boron tribromide (5g, 20mmol) dissolved in 10ml of anhydrous dichloromethane at room temperature, when the boron tribromide solution was added dropwise , continue to react at room temperature for 8 hours; stop the reaction, pour the reaction solution into ice water, extract three times with dichloromethane, then wash three times with saturated aqueous sodium chloride solution and water, dry in anhydrous magnesium sulfate, filter, The dichloromethane solution was removed by rotary evaporation under reduced pressure, and the crude product was purified by column chromatography. The eluent was petroleum ether:dichloromethane=1:3, and a gra...

Embodiment 2

[0034] 4,4'-Di-(4,4,5,5-1,3,2-dioxaborolane-diyl)-4”-(2-(2-(2-methoxyethoxy) Synthesis of Ethoxy) Ethoxy)-Triphenylamine (3)

[0035]

[0036] Under nitrogen atmosphere, 4,4'-dibromo-4"-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-triphenylamine (5.65 g, 10 mmol) was dissolved In 100mL of anhydrous tetrahydrofuran (THF) solution, cool down to -78°C, slowly add 2.5mol / L n-BuLi (14mL, 35mmol) dropwise, keep stirring at this temperature for 2 hours, and quickly dissolve 2-isopropyl Base-4,4,5,5-tetramethyl-1,3,2-dioxaborane (7.44g, 40mmol) was added, naturally raised to room temperature, stirred for 24h, quenched with 5ml of distilled water, and evaporated THF was removed, the product was extracted with dichloromethane, washed with saturated sodium chloride water three times, dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. The crude product was recrystallized in a methanol / tetrahydrofuran mixed solution to obtain a white solid, the product ...

Embodiment 3

[0038] Synthesis of 4,4'-dibromo-4"-((methoxymethoxy)methoxy)triphenylamine (5)

[0039]

[0040] (1) Synthesis of (methoxymethoxy)methoxy-4-methylbenzenesulfonate (4): under nitrogen protection, (methoxymethoxy)methanol (0.92g, 10mmol), three Ethylamine (1.01g, 10mmol) was dissolved in 20ml of anhydrous dichloromethane, cooled to 0°C in an ice bath, and then 10ml of anhydrous dichloromethane solution dissolved with p-toluenesulfonyl chloride (1.90g, 10mmol) was dropped Add it into the reaction bottle, after the dropwise addition is completed, let it rise to room temperature and react for 8 hours; extract with dichloromethane, wash with saturated sodium chloride solution for 3 times, dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and purify the crude product by column chromatography , the eluent was petroleum ether:ethyl acetate=5:1, and a colorless liquid was obtained with a yield of 82%. (Mass Spec - APCI: 246.4).

[0041] (2) Synthesis ...

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Abstract

The invention discloses a triphenylamine polymer containing an oligoether side chain and its application in the preparation of an organic photoelectric device by a solution method. The polymer of the present invention has simple structure and is easy to synthesize. The planar triphenylamine unit obtained by triphenylamine through bridging reaction is the main chain, which is conducive to improving the hole mobility and making the polymer have higher hole transport ability, which is very good. Hole injection / transport / generation materials; the HOMO / LUMO energy level of the polymer can be adjusted, triphenylamine can be polymerized with different Ar units to obtain polymer materials with different energy levels, and the oligomeric ether side chain of the polymer makes the polymerization The polymer has good solubility in medium polar solvents containing oxygen cycloalkane, but poor solubility in strong polar solvents, so that polymers have more solvent orthogonal choices in multilayer solution processing devices. The triphenylamine polymer containing oligoether side chains of the invention is applied to the preparation of organic photoelectric devices by a solution method.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to triphenylamine polymers containing oligoether side chains and their application in the preparation of organic photoelectric devices by a solution method. Background technique [0002] Organic / polymer light-emitting diodes (O / PLEDs) are a class of light-emitting diodes based on small organic molecules and polymer materials. It has the advantages of light weight, active light emission, wide viewing angle, low cost, low energy consumption, easy fabrication of flexible and large-size panels, etc., and has broad application prospects in the fields of organic flat panel display and white light lighting. Organic solar cell materials are a new class of sustainable renewable low-cost green energy materials, and are easy to prepare large-area flexible batteries, so they have great application potential. Organic field-effect transistors are transistor devices that use organic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54
CPCC08G61/12C08G61/122C08G61/124C08G61/126C08G2261/92C08G2261/5222C08G2261/512C08G2261/411C08G2261/344C08G2261/91C08G2261/1424C08G2261/122C08G2261/11C08G2261/124C08G2261/3223C08G2261/3162C08G2261/3241C08G2261/3142C08G2261/312H10K85/111H10K85/113H10K50/00H10K2102/00H10K2102/301Y02E10/549
Inventor 杨伟彭沣应磊郭婷何锐锋彭俊彪
Owner SOUTH CHINA UNIV OF TECH
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