Bipolar polymer luminescent material based on diarylamine group as well as preparation method and application thereof

A diarylamine-based, luminescent material technology, applied in luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., to achieve the effects of improving device efficiency, enriching optical and electrical properties, and high fluorescence quantum yield

Inactive Publication Date: 2017-07-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a bipolar polymer light-emitting material based on diarylamine groups for the problems faced by the current polymer light-emitting diode (PLED).

Method used

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  • Bipolar polymer luminescent material based on diarylamine group as well as preparation method and application thereof
  • Bipolar polymer luminescent material based on diarylamine group as well as preparation method and application thereof
  • Bipolar polymer luminescent material based on diarylamine group as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Preparation of 2-bromofluorene

[0061]In a 250mL three-necked flask, add fluorene (16.6g, 0.1mol), iron powder (88mg, 1.57mmol), and 100mL of chloroform; cool in an ice-water bath, add bromine (17.6g, 0.1mol) / chloroform mixed solution dropwise 35mL, the temperature in the bottle does not exceed 5°C when adding dropwise. Reacted for 16 hours, filtered and recrystallized from chloroform to obtain 19.3 g of white solid with a yield of 84%. 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:

[0062]

Embodiment 2

[0064] Preparation of 2-bromo-9,9-dioctylfluorene

[0065] Add 2-bromofluorene (7.4g, 0.03mol), benzyltriethylammonium chloride (0.07g, 0.3mmol), dimethyl sulfoxide 90mL, 45mL sodium hydroxide aqueous solution (50wt%) in the three-necked flask, Stir at room temperature to form a suspension; add 1-bromo-n-octane (12.5 g, 65 mmol) dropwise, and continue stirring for 3 hours, then extract with ether; wash the ether phase with saturated aqueous sodium chloride and dry over anhydrous magnesium sulfate. The solvent was evaporated, and the product was purified by column chromatography using petroleum ether as the eluent to obtain a white solid. 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:

[0066]

Embodiment 3

[0068] Preparation of 2-boronate-9,9-dioctylfluorene

[0069] Under an argon atmosphere, 2-bromo-9,9-dioctylfluorene (5 g, 10.65 mmol) was dissolved in 180 mL of refined tetrahydrofuran (THF), and 1.6 mol.L was gradually added dropwise at -78 ° C -1 28mL of n-butyllithium, reacted for 2 hours, then added 25mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane, at -78°C The reaction was continued for 1 hour, and the temperature was 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 (petroleum ether / ethyl acetate=20 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid, the product rate of 70%. 1 H NMR, 13 CNMR, MS...

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Abstract

The invention discloses a bipolar polymer luminescent material based on a diarylamine group as well as a preparation method and an application thereof. The bipolar polymer luminescent material based on the diarylamine group is prepared by simultaneous induction of an electron-withdrawing electron-transporting unit dibenzothiophene dioxide and an electron-donating hole-transporting unit diarylamine group on a main chain of the polymer, and an end-capping reaction by using phenylboronic acid and bromobenzene in order. The polymer main chain simultaneously contains the electron-transporting unit and the hole-transporting unit, which benefits for carrier injection and transporting balance, and improves efficiency of devices. The bipolar polymer luminescent material based on the diarylamine group has good dissolvability, is suitable for carrying out solution processing and printing display, and is used for preparing a luminescent layer of an organic light-emitting diode; preparation of electroluminescent devices from the polymer does not need annealing processing, so that the preparation technology is simpler.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and specifically relates to a diarylamine group-based bipolar polymer luminescent material 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 electronics has attracted the attention of numerous research institutions and scientific research teams around the world. Among them, the development of new efficient and stable materials has become the key. [0003] However, the current organic light-emitting device technology h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/54
CPCC09K11/06C08G61/12C08G61/126C08G2261/411C08G2261/512C08G2261/514C08G2261/5222C08G2261/12C08G2261/3162C08G2261/3142C08G2261/3243C08G2261/1412C08G2261/1424C08G2261/148C08G2261/18C08G2261/95C09K2211/1458H10K85/113H10K85/151
Inventor 应磊赵森郭婷杨伟彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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