Compound containing diphenyl sulfone skeleton and preparation method and application thereof

A technology of diphenyl sulfone and compound, which is applied in the application field of organic electroluminescent materials, can solve the problems of aggregation-induced quenching, low exciton utilization rate, etc., and achieves simple preparation method, high product yield and purity, and luminous efficiency. high effect

Active Publication Date: 2021-09-24
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In summary, TADF materials can make full use of singlet and triplet excitons to emit light, and have high exciton utilization efficiency. The disadvantage of this material is that it will produce aggregation-induced quenching (ACQ) effect; AIE materials have high Solid-state luminous efficiency, the disadvantage of this material is that it can only use singlet excitons to emit light, and the exciton utilization rate is low

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  • Compound containing diphenyl sulfone skeleton and preparation method and application thereof
  • Compound containing diphenyl sulfone skeleton and preparation method and application thereof
  • Compound containing diphenyl sulfone skeleton and preparation method and application thereof

Examples

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Embodiment 1

[0033] Example 1, 10-(4-((3,5-bis(9hydro-carbazol-9-yl)phenyl)sulfonyl)phenyl)-9,9-dimethyl-9,10-di The preparation of hydrogen acridine, step is as follows:

[0034] (1) Synthesis and Characterization of 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole)

[0035]Under nitrogen protection, 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole) (5.2g, 10.7mmol), 4-chloromercaptobenzene (1.55g, 10.7mmol ), potassium tert-butoxide (3.6g, 32.1mmol), bis[2-(diphenylphosphino)phenyl]ether (0.54mmol, 0.29g), tridibenzylideneacetone dipalladium (0.54mmol, 0.49 g) Dissolve in 130 mL of toluene. The mixture was refluxed at 125°C for 12 hours. It was then cooled to room temperature and the reaction was quenched with water. Extract with dichloromethane and wash the organic layer with brine. Thereafter, the solvent was spin-dried under reduced pressure, and the crude product was purified by silica gel column chromatography to obtain a white solid 9,9'-(5-((4-chlorophenyl)thio)-1,3-phenylene)bis( 9...

Embodiment 2

[0041] Embodiment 2, structure, preparation and performance of organic electroluminescence device:

[0042] A non-doped organic electroluminescent device A prepared by us, the structure of the device is: ITO / HATCN, thickness 30nm / TAPC, thickness 25nm / the compound containing diphenylsulfone skeleton described in claim 1, thickness 40nm / TmPyPB, thickness 40nm / LiF, thickness 1nm / Al, thickness 150nm;

[0043] A doped organic electroluminescence device B or C structure prepared is: ITO / HATCN, thickness 20nm / TAPC, thickness 25nm / mass fraction 10% or 20% compound CZ-DPS-DMAC:DPEPO, thickness 40nm / TmPyPB, thickness 40nm / LiF, thickness 1nm / Al, thickness 150nm. Among them, HATCN is used as a hole injection layer, and TAPC is used as a hole transport layer; 10-(4-((3,5-bis(9 hydrogen-carbazol-9-yl)phenyl)sulfonyl)phenyl)-9 ,9-Dimethyl-9,10-dihydroacridine was used as the light-emitting layer; TmPyPB was used as the electron-transporting layer.

[0044] Preparation steps of the devic...

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Abstract

The invention provides a compound containing diphenyl sulfone as a skeleton and a preparation method and application thereof, and the name of the compound is 10-(4-((3, 5-bis (9H-carbazole-9-yl) phenyl) sulfonyl) phenyl)-9, 9-dimethyl-9, 10-dihydroacridine. The preparation method comprises the following steps: carrying out a carbon-carbon coupling reaction on 9, 9'-(5-bromo-1, 3-phenylene) bis (9H-carbazole) and 4-chloro-1, 2-dimercaptobenzene to synthesize 9, 9'-(5-((4-chlorphenyl) sulfo)-1, 3-phenylene) bis (9H-carbazole); oxidizing the 9, 9'-(5-((4-chlorphenyl) sulfo)-1, 3-phenylene) bis (9H-carbazole) by using m-chloroperoxybenzoic acid to obtain 9, 9'-(5-((4-chlorphenyl) sulfonyl)-1, 3-phenylene) bis (9H-carbazole); finally, enabling the 9'-(5-((4-chlorphenyl) sulfonyl)-1, 3-phenylene) bis (9H-carbazole) and 9, 10-dihydro-9, 9-dimethyl acridine to be subjected to a Ullmann coupling reaction, and obtaining the target compound. The compound has excellent thermal stability, electrochemical stability, charge transfer performance and luminescence performance, and can be used as a blue organic electroluminescent material.

Description

technical field [0001] The present invention relates to heterocyclic compounds containing carbon, hydrogen, oxygen, nitrogen and sulfur, and specifically belongs to a compound with diphenyl sulfone as the skeleton and carbazole and 9,9-dimethyl-9,10-dihydroacridine as the donor A compound of a body group, a preparation method thereof, and an application of the compound as an organic electroluminescent material. Background technique [0002] Thermally Activated Delayed Fluorescence (TADF), which utilizes triplet excitons by other means, has a small singlet-triplet energy gap (ΔE ST ), under the action of ambient heat, the triplet excitons can be effectively upconverted to singlet excitons to emit light, so that the fluorescence internal quantum efficiency can reach 100%. This material can combine the advantages of fluorescent and phosphorescent materials at the same time, and is called the third-generation organic light-emitting material. In 2012, based on the study of pure...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09K11/06H01L51/54H01L51/50
CPCC07D401/14C09K11/06C09K2211/1029C09K2211/1014C09K2211/1007H10K85/6572H10K50/11
Inventor 霍晋楠施和平郑雅楠
Owner SHANXI UNIV
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