Asymmetrical thermal-activation-delayed aggregation-induced emission material based on diphenyl sulfone phenoxazine, as well as synthesis method and application of material

A technology of aggregation-induced luminescence and thermal activation delay, which can be used in luminescent materials, chemical instruments and methods, semiconductor devices, etc. Effects of simple transition temperature, synthesis method and purification process, and excellent luminescence properties

Active Publication Date: 2015-11-11
SUN YAT SEN UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

This doping method has many disadvantages, for example, it is difficult to control the ratio between the host and the guest during the vac

Method used

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  • Asymmetrical thermal-activation-delayed aggregation-induced emission material based on diphenyl sulfone phenoxazine, as well as synthesis method and application of material
  • Asymmetrical thermal-activation-delayed aggregation-induced emission material based on diphenyl sulfone phenoxazine, as well as synthesis method and application of material
  • Asymmetrical thermal-activation-delayed aggregation-induced emission material based on diphenyl sulfone phenoxazine, as well as synthesis method and application of material

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preparation example Construction

[0037] The synthesis method of thermally activated delayed fluorescent material of the present invention comprises the following steps:

[0038] (1) Connect fluorobenzene to 4-iodobenzenesulfonyl through Friedel-Crafts reaction to obtain the first intermediate 1-(4-fluorobenzenesulfonyl)-4-iodobenzene.

[0039] (2) connecting the phenoxazine to the first intermediate prepared in step (1) through a coupling reaction to obtain the second intermediate. Specifically, the coupling reaction for synthesizing the second intermediate is realized by the following method: the first intermediate is reacted with phenoxazine under the action of potassium tert-butoxide to synthesize the second intermediate.

[0040](3) Phenylboronic acid, carbazole, diphenylamine, phenothiazine, phenoxazine, dimethylacridine, 3,6-di-tert-butylcarbazole, triphenylamine borate, 4-(9-carbazolyl ) A kind of in phenylboronic acid or N-phenylcarbazole-3-boronic acid is connected on other carbazoles by coupling re...

Embodiment 1

[0045] Example 1: 10-(4-((4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)sulfonyl)phenyl)-10H-phen Synthesis of oxazines

[0046] (1) Synthesis of the first intermediate 1-(4-fluorobenzenesulfonyl)-4-iodobenzene:

[0047]

[0048] Add 4-iodobenzenesulfonyl chloride (5.91g, 19.53mmol) and fluorobenzene (2.81g, 29.30mmol) into a 250mL three-necked flask, add ferric chloride (7.91g, 48.83mmol) and heat the reaction solution to 40 ° C and stirred the reaction for 3h. The reaction solution was cooled to room temperature, 30 mL of dichloromethane and 50 mL of 1M dilute hydrochloric acid were added successively and stirred for 10 min, the mixed solution was poured into a separatory funnel, the organic layer solution was taken, dried with anhydrous sodium sulfate, and suction filtered, and the obtained filtrate was The solvent was spin-dried by the evaporator, and the remaining solid was vacuum-dried to obtain 6.72 g of yellow-white powder, with a yield of 95%.

[0049] (2) Synthesi...

Embodiment 2

[0055] Example 2: Synthesis of 10-(4-((4-(9H-[3,9'-dicarbazol]-9-yl)phenyl)sulfonyl)phenyl)-10H-phenoxazine

[0056] (1) Synthesis of intermediate 3-bromo-9-tosyl-9H-carbazole:

[0057]

[0058] Add 3-bromocarbazole (5.00g, 20.32mmol), potassium hydroxide (3.41g, 60.95mmol) and 50mL of acetone into a 250mL three-neck flask and stir for 10min, add p-toluenesulfonyl chloride (11.62g, 60.95mmol), and heat to reflux After 1 hour, a large amount of white solid was observed to be precipitated, which was filtered by suction. The solid was washed twice with a small amount of ethanol and dried in vacuo to obtain 7.48 g of white powder with a yield of 92%.

[0059] (2) Synthesis of intermediate 3-(9H-carbazol-9-yl)-9-tosyl-9H-carbazole:

[0060]

[0061] The intermediate 3-bromo-9-tosyl-9H-carbazole (1.00g, 2.50mmol), carbazole (0.63g, 3.75mmol), K 2 CO 3 (1.03g, 7.49mmol), 1,10-phenanthroline (0.10g), 18-crown-6 (0.10g), cuprous iodide (0.20g) and 30mL DMF were added to a 250m...

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Abstract

The invention discloses an asymmetrical thermal-activation-delayed aggregation-induced emission material based on a diphenyl sulfone phenoxazine, as well as a synthesis method and application of the material. A core structure of the material comprises a diphenyl sulfone unit and a phenoxazine group, and further comprises an electronic structure unit made from aryl heterocyclic groups except a phenoxazine substituent. The synthesis method and the purification process of the material are simple, the thermal performance, luminous performance and the like of an end product can be adjusted according to the connection of different groups, the obtained emission material has thermal-activation-delayed fluorescent and aggregation-induced emission performance at the same time, is good in heat stability, higher in glass transition temperature and excellent in luminous performance. A non-doped OLED device manufactured by using the emission material as the luminous layer is high in luminous brightness and good in stability, so that the luminous efficiency and the service life of the OLED device can meet the practical requirements.

Description

technical field [0001] The present invention relates to the field of thermally activated delayed fluorescent materials, in particular to a thermally activated delayed fluorescent (TADF) material with aggregation-induced emission (AIE) properties of asymmetric molecular structure, its synthesis method and the use of the asymmetric type with AIE properties Undoped OLED devices of TADF materials. Background technique [0002] Organic light-emitting diodes (OLEDs) have been highly valued by the scientific and industrial circles due to their advantages such as low driving voltage, fast response, rich colors, wide viewing angles, and flexibility. A generation of display technology with huge potential applications. [0003] However, at present, OLED technology has encountered many difficulties in the development process. For example, the luminous efficiency, service life of the device, and the preparation process required for industrial production are difficult to meet the practic...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D413/12C07D265/38C07D417/12C07D487/04C07D413/14C07D417/14H01L51/54
Inventor 许炳佳穆英啸毛竹谢宗良池振国张艺许家瑞金崇君
Owner SUN YAT SEN UNIV
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