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Thiazole-based organic electroluminescent material and preparation method thereof

An electroluminescent material and organic technology, applied in the direction of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of difficult to balance hole and electron transport efficiency, poor electroluminescence efficiency, etc.

Inactive Publication Date: 2020-08-21
胡金超
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention provides a thiazole-based organic electroluminescent material and a preparation method thereof, which solves the technical problem that existing organic electroluminescent materials are difficult to take into account the transport efficiency of holes and electrons, and the electroluminescent efficiency is poor

Method used

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  • Thiazole-based organic electroluminescent material and preparation method thereof
  • Thiazole-based organic electroluminescent material and preparation method thereof
  • Thiazole-based organic electroluminescent material and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Under nitrogen protection, 9,9-bis(4-tetrazolylphenyl)fluorene (1.5g, 3.3mmol) and 15mL pyridine were added to a 50ml two-necked flask, and 4-tert-butylbenzene was added dropwise to the mixed solution. Formyl chloride (2 mL, 10 mmol). The reaction mixture was heated at 130 °C for 4 hours. After the reaction was completed, the reaction solution was poured into a mixture of water and MeOH (150 mL, 1:3), dried, filtered, and the solvent was removed by a rotary evaporator. The crude product was subjected to silica gel column chromatography (the eluent was petroleum ether: ethyl acetate = 4:1), and in toluene / CHCl 3 Recrystallization in (5:1) yielded 5,5'-(((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(2-(4-(tert Butyl) phenyl)-1,3,4-oxadiazole) (2.3g, yield 90.3%), its reaction equation is as follows:

[0029]

Embodiment 2

[0031] Under a nitrogen atmosphere, add 5,5'-(((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(2-(4 -(tert-butyl)phenyl)-1,3,4-oxadiazole) (0.5g, 0.70mmol) and CHCl 3 (50mL), stir well and add trifluoroacetic acid (0.5g, 1.16mmol) and bromine (0.24gg, 1.50mmol) to the mixed solution. The reaction mixture was stirred at 50 °C for 48 h, then washed with 100 ml NaHCO 3 Wash with aqueous solution until the red color of bromine disappears. The organic layer was washed with Na 2 SO 4 Dry and remove solvent in vacuo. The residue passes through CH 2 Cl 2 / ethyl acetate (20:1) eluent was subjected to silica gel column chromatography to obtain 5,5'-(((2,7-dibromo9H-fluorene-9,9-diyl)bis(4, 1-phenylene))bis(2-(4-(tert-butyl)phenyl)-1,3,4-oxadiazole) (0.4g, yield 65.0%), the reaction equation is as follows:

[0032]

Embodiment 3

[0034] 5,5'-(((2,7-dibromo9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(2-(4-(tert-butyl)benzene base)-1,3,4-oxadiazole) (11.36g, 15mmol), 2-isopropyl-4,4',5,5'-tetramethyl-1,3,2-dioxaborin Put alkane (16.3mL, 80mmol) into a 250ml three-necked flask, dissolve it in 80mL toluene, stir and dissolve at room temperature in an argon atmosphere, and then raise the temperature to 80°C for 18h. Stop the reaction and pour the reaction solution into water to quench it. The reaction solution was concentrated and extracted with dichloromethane, purified by column chromatography, using 200-300 mesh silica gel as the stationary phase, and the eluent was petroleum ether / dichloromethane (2:1), to obtain 2-(3-( 3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-14H-bis(dibenzothiophene)pyrrole-5-benzene Base-1,3,4-oxadiazole (10.1g, yield 70%), its chemical reaction equation is:

[0035]

[0036] Example 3

[0037] Add 2-aminobenzaldehyde (4.8g, 40mmol) and 50mL of acetone into a 250mL ...

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PUM

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Abstract

The invention belongs to the technical field of photoelectric display devices, and particularly relates to a thiazole-based organic electroluminescent material and a preparation method thereof. The thiazole-based organic electroluminescent material provided by the invention has a structure as shown in a formula (I). The invention also provides a preparation method of the thiazole-based organic electroluminescent material. The method comprises the step of subjecting a compound as shown in the formula (II), 3,10-dibromo-14-(3-(5-phenyl-1,3,10-oxadiazol-2-yl)phenyl)-14H-bis(S,S-dioxo-dibenzothiophene)pyrrole and 2-(3-(3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-14H-bis(S,S-dioxo-dibenzothiophene)pyrrole-1, 5-phenyl-1,3,4-oxadiazole to a Suzuki coupling reaction so as to obtain a polymer as shown in a formula (I). The thiazole-based organic electroluminescent material and the preparation method thereof solve the technical problem that existing organic electroluminescent materialsare difficult to guarantee both hole and electron transport efficiency and are thus poor in electroluminescent efficiency.

Description

technical field [0001] The invention belongs to the technical field of photoelectric display devices, and in particular relates to a thiazole-based organic electroluminescence material and a preparation method thereof. Background technique [0002] The 21st century is called a brand-new "electronic information age". The development of the network has increased people's demand for information. Smart phones, watches, and (tablet) computers have become an indispensable part of people's lives. The advent of the information age has greatly promoted the development of display technology. People's pursuit of thinner and more energy-saving large-size, flexible displays has made organic electroluminescence become the mainstream of the market. Organic electroluminescent diodes have the advantages of low-voltage drive, pixel self-luminescence, fast response, wide viewing angle, and thin thickness. They are solid-state full-color displays that can be processed with flexible substrates a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/54H01L51/50
CPCC08G61/123C09K11/06C08G2261/122C08G2261/1412C08G2261/148C08G2261/149C08G2261/3245C08G2261/3142C08G2261/411C08G2261/5222C08G2261/95C09K2211/1475C09K2211/1483C09K2211/1416C09K2211/1425H10K85/113H10K85/151H10K50/11
Inventor 胡金超
Owner 胡金超
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