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A thermally activated delayed fluorescence conjugated polymer luminescent material containing a sulfone group in the side chain, its preparation method and application

A technology of conjugated polymers and thermal activation delay, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc. It can solve the problems of lower performance than small molecule materials and less materials, and achieve large molecular weight and stability Good performance and improved performance

Active Publication Date: 2019-04-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the high-efficiency red, green, and blue thermally activated delayed fluorescent materials reported in the literature are all small molecule materials, and the thermally activated delayed fluorescent polymer materials reported in the literature are few, and their performance is far lower than that of small molecule materials.

Method used

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  • A thermally activated delayed fluorescence conjugated polymer luminescent material containing a sulfone group in the side chain, its preparation method and application
  • A thermally activated delayed fluorescence conjugated polymer luminescent material containing a sulfone group in the side chain, its preparation method and application
  • A thermally activated delayed fluorescence conjugated polymer luminescent material containing a sulfone group in the side chain, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Preparation of 2,7-dibromofluorene

[0062] In a 1000mL three-neck flask, add fluorene (60g, 301mmol), iron powder (0.84g, 15mmol) and chloroform (400mL), and put liquid bromine (35mL, 753mmol) and 115mL chloroform The mixed solution was slowly added dropwise into the reaction solution, and after the addition was completed, the reaction was vigorously stirred at room temperature for 12 hours. Add 200 mL of a saturated aqueous solution of sodium bisulfite to the reaction flask to quench the reaction. The reaction mixture was suction filtered, and the filter residue was washed three times successively with saturated aqueous sodium bisulfite solution, water and ethanol. After the filter residue was dried, it was washed with CHCl 3 Purification was carried out by recrystallization to obtain 77.8 g of white crystals, yield: 80%. 1 H NMR (300MHz, CDCl 3 ) (ppm): 7.54 (d, 2H), 7.44 (d, 2H), 7.31 (d, 2H), 3.86 (m, 2H). 13 C NMR (75MHz, CDCl 3 ) (ppm): 152.91, 144.49, 134.8...

Embodiment 2

[0065] Preparation of 2,7-dibromo-9,9-dioctylfluorene (M-1)

[0066] Under the protection of argon, in a 500mL three-necked flask, add 2,7-dibromofluorene (32.4g, 100mmol) and dimethyl sulfoxide (250mL), under vigorous stirring, add tetrabutylammonium bromide (1.61g , 5mmol), and then slowly dropwise added sodium hydroxide (40g, 1000mmol) 50wt% aqueous solution, after the addition was completed, reacted for 2 hours, and then injected 1-bromooctane (57.9g, 300mmol) in one go. After continuing to react for 10 hours, stop the reaction, pour the reaction solution into water, add aqueous hydrochloric acid for neutralization, extract with dichloromethane, wash 7 times with saturated brine, dry, spin dry the solvent, and use column chromatography to analyze the crude The product was purified by using silica gel as a fixation and petroleum ether as a fluidity. After purification, 43.8 g of a white solid was obtained with a yield of about 80%. 1 H NMR (300MHz, CDCl 3 )(ppm): 7.53(d, ...

Embodiment 3

[0069] Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (M-2)

[0070] Under the protection of argon, add 2,7-dibromo-9,9-dioctylfluorene (21.9g, 40mmol) and 250mL of anhydrous tetrahydrofuran into a 500mL three-neck flask, and cool the reaction liquid to -78°C with liquid nitrogen. ℃, slowly drop n-butyllithium in n-hexane solution (48mL, 2.5M, 120mmol), keep stirring at -78℃ for 2 hours, inject 2-isopropyl-4,4,5,5-tetra Methyl-1,3,2-dioxaborane (26g, 140mmol), let it rise to room temperature naturally, and continue to react for 20h. Add ammonium chloride 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 spin-dried the solvent, and the crude product is analyzed by column chromatography. The product was purified by using silica gel as a fixation and petroleum ether...

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Abstract

The invention discloses a thermally activated delayed fluorescence (TADF) conjugated polymer luminescent material containing a sulfone group in the side chain, a preparation method and an application thereof. The main feature of the material is that the side chain of the polymer contains sulfone groups, and the preparation method mainly includes the synthesis of TADF units containing sulfone groups and the synthesis of TADF conjugated polymers by Suzuki coupling polymerization. The TADF emission of the polymer is realized by adjusting the content of TADF units containing sulfone groups in the polymer and the molar ratio of the copolymerized units. The synthesized TADF conjugated polymer containing sulfone groups in the side chain has a relatively large molecular weight and good solubility, thereby obtaining a new type of high-efficiency TADF polymer luminescent material with a new structure.

Description

technical field [0001] The invention belongs to the technical field of organic macromolecule electroluminescence, in particular to a thermally activated delayed fluorescence (TADF) conjugated polymer luminescent material containing a sulfone group in a side chain, a preparation method and an application thereof. Background technique [0002] The luminous brightness and efficiency of polymer devices are lower than those of organic small molecule devices, but they have excellent electrical and thermal stability, can be made into flexible devices, have good mechanical processing characteristics, and can be formed into films by spin coating or inkjet printing. As well as the advantages of changing the emission wavelength by changing and modifying its molecular chain. Polymer light-emitting diodes (PLEDs) have received extensive attention due to their promising applications in large-area flat-panel displays. At present, the research on organic / polymer light-emitting materials an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/54C09K11/06
CPCC09K11/06C08G61/12C08G61/122C08G61/124C08G61/126C08G2261/344C08G2261/1412C08G2261/145C08G2261/122C08G2261/3142C08G2261/148C08G2261/149C08G2261/3241C08G2261/95C08G2261/522C08G2261/411H10K85/113
Inventor 郭婷杨伟应磊胡黎文曹镛
Owner SOUTH CHINA UNIV OF TECH
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