Polymer luminescent material, preparation method and use thereof

A technology of luminescent materials and polymers, applied in the direction of luminescent materials, chemical instruments and methods, etc., to achieve the effect of improving photophysical properties, high fluorescence quantum efficiency and device efficiency

Active Publication Date: 2018-11-23
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Overall, the currently known polymer thermally excited delayed fluorescence materials are still less selected, and it is still necessary to synthesize new solution-processable polymer thermally excited delayed fluorescent materials

Method used

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  • Polymer luminescent material, preparation method and use thereof
  • Polymer luminescent material, preparation method and use thereof
  • Polymer luminescent material, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0082] Preparation Example 1: Synthesis of 2-(2-ethylhexyl)-8-phenothiazine dibenzothiophene sulfone

[0083] 1) Synthesis of 2-bromodibenzothiophene

[0084]

[0085] Under ice-water bath conditions, dibenzothiophene (0.1 mol) was dissolved in 100 ml of anhydrous CHCl in the reactor 3 , then use 20ml of anhydrous CHCl 3 Dissolve 5.4ml of liquid bromine in a constant pressure funnel and add it dropwise to the reactor. React at room temperature for three days. Add 30ml saturated NaHSO 3 solution, stirred until the solution was white, and the organic layer was extracted. Then the reaction solution was poured into a separatory funnel, extracted 3 times with dichloromethane, and washed 3 times with saturated NaCl aqueous solution. The organic layer was dried with anhydrous sodium sulfate, filtered, spin-dried, and recrystallized from ethanol to obtain 25.2 g of a white solid with a yield of 96%.

[0086] 2) Synthesis of 2-(2-ethylhexanoyl)-8-bromo-dibenzothiophene

[0...

preparation example 2

[0095] Preparation Example 2: Synthesis of N-heptylcarbazole

[0096] Carbazole (50mmol) was dissolved in N,N-dimethylformamide DMF (100mL), and 60wt% NaH (75mmol) dispersed in kerosene was slowly added at 0°C and stirred for 3h. After the temperature naturally rose to room temperature, a solution of 1-bromo-n-heptane (55 mmol) in DMF (20 mL) was slowly dropped into the reaction system, and the reaction was continued for 12 h. After the reaction was completed, water was added to quench the reaction, and the organic phase was extracted with dichlorohexane. After spin-drying, the mixture of dichloromethane and n-hexane with a volume ratio of 1:5 was used as the eluent for column chromatography to obtain 11.8 g of a yellow solid with a yield of 89%. 1 H NMR (400MHz, Acetone-d6): δ8.11 (d, J = 7.8Hz, 2H), 7.50 (d, J = 8.2Hz, 2H), 7.48-7.36 (m, 2H), 7.18 (t, J =7.4Hz, 2H), 4.34 (t, J = 7.2Hz, 2H), 1.37-1.13 (m, 10H), 0.83 (dt, J = 13.7, 6.8Hz, 3H).

[0097]

Embodiment 1

[0099] (1) Synthesis of 2-(2-ethylhexyl)-8-(3,7-dibromophenothiazine) dibenzothiophene sulfone (terminal brominated monomer A)

[0100]

[0101]2-(2-Ethylhexyl)-8-phenothiazinedibenzothiophene sulfone (4 mmol) was dissolved in 50 mL of dry dichloromethane. In an ice-water bath and protected from light, a solution of NBS (8.4 mmol) in dry dichloromethane was slowly added dropwise thereto. After stirring at room temperature for 20 h, the reaction liquid was added into water to terminate the reaction. Afterwards, the organic phase was extracted with dichloromethane, dried over magnesium sulfate, and spin-dried. Using a mixture of n-hexane and dichloromethane (the volume ratio of the two is 1:1) as the eluent for column chromatography to obtain 2.5 g of light yellow solid with a yield of 91%. 1 H NMR (400MHz, DMSO-d6): δ8.32(s, 1H), 8.22(d, J=8.1Hz, 1H), 8.10(s, 1H), 8.41-7.68(m, 8H), 7.92(d ,J=7.9Hz,1H),7.65(d,J=8.1Hz,1H),7.48(d,J=7.9Hz,1H),7.43(s,2H),7.18(d,J=8.8Hz,2H ),6...

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Abstract

The invention discloses a polymer luminescent material, a preparation method and use thereof. The polymer luminescent material with a regulable physical property is synthesized by copolymerizing suitable thermally excited delayed fluorescent unit alkyl-substituted phenothiazine-dibenzothiophene sulfone with a host unit. The material can obtain high fluorescence quantum efficiency and device efficiency, and is suitable for being used as a light-emitting layer material in a solution processing type organic electroluminescence device.

Description

technical field [0001] The invention relates to a polymer luminescent material and its preparation method and application, in particular to a preparation method and application of an adjustable polymer luminescent material with thermally excited delayed fluorescence. Background technique [0002] Organic light-emitting diodes (OLEDs) were discovered in the laboratory by Chinese-American professor Ching W. Tang in 1979. In view of the advantages of OLED display technology, such as self-illumination, wide viewing angle, low driving voltage, high contrast ratio, and fast response, more and more people pay more and more attention to it. However, conventional OLED devices are limited by electron spin prohibition, and the highest internal quantum efficiency (IQE) is only 25%. [0003] Subsequently, people have developed organic phosphorescent materials that use the atomic effect of heavy metals to break the spin-forbidden limitation, so that the IQE is close to 100%. Due to the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06
CPCC08G61/122C08G61/126C08G2261/122C08G2261/124C08G2261/1412C08G2261/145C08G2261/18C08G2261/3241C08G2261/3246C08G2261/411C08G2261/5222C08G2261/95C09K11/06C09K2211/1416C09K2211/1458C09K2211/1466C09K2211/1483
Inventor 任忠杰刘玉超闫寿科孙晓丽李慧慧
Owner BEIJING UNIV OF CHEM TECH
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