Trianiline thiofluorene unit-based blue light conjugated polymer, and preparation method and application thereof

A conjugated polymer, triphenylamine technology, used in electrical components, semiconductor/solid-state device manufacturing, circuits, etc., to achieve the effect of improving device efficiency, good solubility, and balanced injection and transmission

Inactive Publication Date: 2019-05-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a blue light conjugated polymer based on triphenylamine thiooxyfluorene unit for the problems faced by current polymer light-emitting diodes (PLEDs).

Method used

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  • Trianiline thiofluorene unit-based blue light conjugated polymer, and preparation method and application thereof
  • Trianiline thiofluorene unit-based blue light conjugated polymer, and preparation method and application thereof
  • Trianiline thiofluorene unit-based blue light conjugated polymer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation of 4-octyl-N,N-diphenylamine

[0053] Under argon protection, in a 250mL two-necked flask, diphenylamine (7.90g, 46.66mmol), p-octylbromobenzene (12.56g, 46.66mmol) and sodium tert-butoxide (25.22g, 233.31mmol) were dissolved in 100mL of toluene , then added tri-tert-butylphosphine (472.03mg, 2.33mmol) and palladium acetate (209.52mg, 933.24umol), heated to 110°C, and reacted for 16 hours. Add aqueous solution to quench the reaction, rotary evaporate most of the solvent, the reaction mixture is poured into water, and extracted with dichloromethane, washed 5 times, the organic phase is separated, dried, filtered, and the crude product is analyzed by column chromatography after spin-drying the solvent. Purification, yield: 78%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:

[0054]

Embodiment 2

[0056] Preparation of 4-bromo-N-(4-octylbenzene)-N-aniline

[0057]Add 4-octyltriphenylamine (35.7g, 0.1mol) and 200mL dimethylformamide into a 500mL three-neck flask, stir until dissolved, dissolve NBS (17.8g, 0.1mol) in 150mL DMF, and cool to about 0°C in an ice bath , slowly add NBS solution dropwise, react in the dark, after the dropwise addition, let the temperature rise automatically, and react for 6 hours. The reaction solution was added dropwise to water to precipitate, and the crude product was extracted with dichloromethane. Dry over anhydrous magnesium sulfate, filter, and spin dry the solvent. The pure substance was separated by column chromatography to obtain a light yellow viscous solid, yield: 88%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:

[0058]

Embodiment 3

[0060] Preparation of Octyltriphenylamine Borate (M1)

[0061] Under an argon atmosphere, 4-bromo-N-(4-octylbenzene)-N-aniline (12.76 g, 29.24 mmol) was dissolved in 180 mL of refined THF, and 1.6 mol L of -1 20mL of n-butyllithium, reacted for 2 hours, then quickly added 20mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane, at -78℃ The reaction was continued for 1 hour, and the temperature was slowly raised to room temperature for 24 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a light yellow viscous crude product was obtained, which was purified by silica gel column chromatography. The product was placed in the refrigerator for a long time to obtain a white solid with a yield of 70%. 1 H NMR, 13 C NMR and GC-MASS tests showed that it was the target product.

[0062]

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Abstract

The invention discloses a trianiline thiofluorene unit-based blue light conjugated polymer, and a preparation method and application thereof. Thiofluorene has a large band gap, so that great reductionof the highest occupied molecular orbital energy level of a polymer is easily caused by introducing the thiofluorene into the polymer; therefore, the injection and transmission balance of holes in anelectroluminescent device are affected. In order to find a balance point in the two aspects of injection and transmission of electrons / holes, the trianiline thiofluorene unit is designed and prepared; the trianiline thiofluorene unit has good hole transmission performance, so that the problem caused by introducing a thiofluorene unit into the main chain of the polymer can be effectively solved. Moreover, a long alkyl chain exists on the trianiline thiofluorene unit, so that the trianiline thiofluorene unit has good solubility; the conjugated polymer which is prepared through a Suzuki polymerization reaction is suitable for performing solution processing and printing displaying. The trianiline thiofluorene unit-based blue light conjugated polymer disclosed by the invention can be used fora light-emitting layer of an organic light emitting diode.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a conjugated polymer based on a triphenylaminothiooxyfluorene unit and a preparation method and application thereof. Background technique [0002] In the past three decades, organic electronics and optoelectronics industries, including organic / polymer light-emitting diodes, organic field-effect transistors, organic solar cells, etc., have developed rapidly and gradually realized industrialization. Organic electronic products have the advantages of low price, light weight and portability. Make it have great market potential. Therefore, the development of market-attractive organic electronic products has attracted the attention of many research institutions and scientific research teams in the world, and among them, the development of new efficient and stable materials has become the key. [0003] The invention provides a triphenylaminothiooxyfluorene ba...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54
Inventor 郭婷应磊胡黎文曹镛
Owner SOUTH CHINA UNIV OF TECH
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