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Fluorescent material containing beta-diketone structure as well as preparation method and application thereof

A fluorescent material and diketone technology, applied in the field of fluorescent materials and OLED devices, can solve the problems of poor effect and low solid-state quantum yield, and achieve the effect of overcoming short fluorescence lifetime, high solid-state quantum yield, and long fluorescence lifetime

Active Publication Date: 2017-12-08
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is because the traditional ESIPT fluorescent material has a low solid-state quantum yield and can only utilize 25% of the singlet excited state excitons.
In order to improve the luminescent properties of ESIPT fluorescent molecules, researchers have tried various methods to improve the structure of ESIPT molecules, see Seki, et.al., Chem.Soc.Rev., Vol 45, (2016), but the results are not good

Method used

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  • Fluorescent material containing beta-diketone structure as well as preparation method and application thereof
  • Fluorescent material containing beta-diketone structure as well as preparation method and application thereof
  • Fluorescent material containing beta-diketone structure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The preparation of 1,3-bis(4-(10H-phenoxazin-10-yl)phenyl)-3-hydroxyprop-2-en-1-one, the reaction process is as follows:

[0060]

[0061] 1.3 g of 1,3-bis(4-bromophenyl)-3-hydroxyprop-2-en-1-one, 1.3 g of phenoxazine, 68 mg of palladium acetate, 270 mg of tri-tert-butylphosphinetetrafluoroboron Acid salt, 670 mg of sodium tert-butoxide and 50 ml of redistilled toluene were added to a 100 ml single-necked round-bottom flask, refluxed for 48 hours under the protection of argon, cooled to room temperature, quenched with saturated brine, extracted with dichloromethane, The organic phase was dried over anhydrous sodium sulfate, filtered and spin-dried. The product was passed through the column at a volume ratio of n-hexane: dichloromethane 1:1 to obtain 1.5 g of the product. Brown-red solid, yield 72%.

[0062] Obtained molecular weight: 586.4.

[0063] Elemental analysis results: C 79.95%, H 4.48%, N 4.78%.

Embodiment 2

[0065] The preparation of 1-(4-(10H-phenoxazin-10-yl)phenyl)-3-hydroxy-3-phenylprop-2-en-1-one, the reaction process is as follows:

[0066]

[0067] 2.1 g of 1-(4-bromophenyl)-3-hydroxy-3-phenylprop-2-en-1-one, 1.3 g of phenoxazine, 68 mg of palladium acetate, 270 mg of tri-tert-butylphosphine tetrafluoro Add borate, 670 mg of sodium tert-butoxide and 50 ml of redistilled toluene into a 100 ml single-necked round-bottom flask, reflux for 48 hours under the protection of argon, cool to room temperature, quench with saturated saline, and extract with dichloromethane , dried the organic phase with anhydrous sodium sulfate, filtered, and spin-dried. 2.3 g of the product was obtained by passing through the column with n-hexane:dichloromethane at a volume ratio of 1:1. Brown-red solid, yield 81%.

[0068] The molecular weight obtained by mass spectrometry: 405.3.

[0069] Elemental analysis results: C 79.99%, H 4.75%, N 3.45%.

Embodiment 3

[0071] The preparation of 1,3-bis(4-(9,9-dimethylacridin-10(9H)-yl)phenyl)-3-hydroxyprop-2-en-1-one, the reaction process is as follows:

[0072]

[0073] 1.3 g of 1,3-bis(4-bromophenyl)-3-hydroxyprop-2-en-1-one, 1.5 g of 9,9-dimethylacridine, 68 mg of palladium acetate, 270 mg of tritert Add butylphosphine tetrafluoroborate, 670 mg sodium tert-butoxide and 50 ml redistilled toluene into a 100 ml single-necked round bottom flask, reflux for 48 hours under argon protection, cool to room temperature, and quench with saturated saline , extracted with dichloromethane, dried the organic phase with anhydrous sodium sulfate, filtered, and spin-dried. The product was passed through the column at a volume ratio of n-hexane: dichloromethane of 1:1 to obtain 1.7 g of the product. Yellow solid, yield 78%.

[0074] Obtained molecular weight: 638.4.

[0075] Elemental analysis results: C 84.75%, H 6.08%, N 4.46%.

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PUM

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Abstract

The invention relates to a fluorescent material which has thermal activation delayed fluorescence and an excited state proton transfer property simultaneously. A D-pi-A-pi-D type strong charge transfer state compound is formed by taking beta-diketone or a derivative thereof with the excited state proton transfer property as a strong pull electron central nucleus (Acceptor), an amine derivative (Donor, D) with a strong electron donating ability as an electron donor and a benzene ring or other aromatic rings as a bridging group. The fluorescent material provided by the invention is simple to prepare and suitable for wide application. Therefore, the organic compound prepared by the invention can replace a conventional thermal activation delayed fluorescent material and an excited state proton transfer material and has important application value and wide prospect in the fields of fluorescence imaging, biosensing, ultraviolent adsorbents, light-emitting apparatuses and the like.

Description

technical field [0001] The invention relates to a fluorescent material and an OLED device prepared by using the fluorescent material. In particular, it relates to a fluorescent material using β-diketone or its derivatives as acceptors and an OLED device prepared by using the fluorescent material. technical background [0002] The biggest feature of excited state proton transfer (ESIPT) molecules is its four-step proton cycle process and large Stokes shift, which has a good application prospect in organic electroluminescence, bioimaging, molecular logic valves, etc. However, traditional ESIPT fluorescent materials generally have the disadvantages of short fluorescence lifetime, low solid-state quantum yield, complex luminescent mechanism and easy environmental influence, which greatly limits their development and application. Organic light-emitting diodes (OLEDs) prepared using ESIPT fluorescent molecules as light-emitting materials generally have a low external quantum effi...

Claims

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Application Information

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IPC IPC(8): C07D265/38C07D279/22C07D219/02C07F7/08C07F7/10C09K11/06H01L51/54
CPCC09K11/06C07D219/02C07D265/38C07D279/22C07F7/0816C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104H10K85/657H10K85/6572H10K85/40
Inventor 杨楚罗吴凯龙龚少龙詹丽思王子安
Owner WUHAN UNIV
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