Tadf material based on large steric hindrance space charge transfer and its synthesis method and application

A technology of space charge and large steric resistance, which is applied in the direction of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of high preparation cost, high price, and efficiency roll-off, and achieve simple synthesis process, adjustable luminous color, The effect of high luminous efficiency

Active Publication Date: 2021-10-08
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, phosphorescent materials mainly use expensive noble metal (iridium, platinum) complexes, so the preparation cost of phosphorescent electroluminescent devices is relatively high.
In addition, phosphorescent electroluminescent materials also have unstable blue-light emitting properties, and the longest service life of electroluminescent devices is only about 1000 hours, which is far from meeting commercial applications; due to the high exciton concentration of phosphorescent electroluminescent materials And the life is longer, so there is a serious efficiency roll-off

Method used

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  • Tadf material based on large steric hindrance space charge transfer and its synthesis method and application
  • Tadf material based on large steric hindrance space charge transfer and its synthesis method and application
  • Tadf material based on large steric hindrance space charge transfer and its synthesis method and application

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preparation example Construction

[0032] The above-mentioned synthetic method based on the large steric hindrance space charge transfer TADF material is characterized in comprising the following steps:

[0033] method one:

[0034] (1) 2-bromobenzenesulfonyl chloride, 2-fluorobenzenesulfonyl chloride, 2-bromobenzoyl chloride or 2-fluorobenzoyl chloride and fluorobenzene or bromobenzene are obtained by Friedel-Crafts reaction of 2-substituted fluoro or Brominated intermediates;

[0035] (2) The intermediate obtained in step (1) and the corresponding boronic acid are subjected to a Sizuki reaction or a substitution reaction with the corresponding aromatic amine to obtain the final product.

[0036] Method Two:

[0037] (1) Reaction of brominated aromatic compound and diboronic acid pinacol ester through Suziki reaction to obtain corresponding boric acid ester intermediate;

[0038] (2) The intermediate obtained in step (1) and the corresponding brominated aromatic hydrocarbon are subjected to Sizuki reaction ...

Embodiment 1

[0043] (1) Synthesis of intermediate [2-bromo-4'-fluorodiphenyl sulfone]

[0044]

[0045]Put 10mmol of 2-bromobenzenesulfonyl chloride and 25mmol of fluorobenzene into a three-necked flask, stir and dissolve under a nitrogen atmosphere, add 13mmol of ferric chloride, and stir at 40°C for 70min. 50 mL of 2M hydrochloric acid was added to terminate the reaction. It was extracted three times with appropriate amount of dichloromethane, and the obtained organic phase was extracted three times with pure water. The organic phase was dried by adding anhydrous sodium sulfate, filtered, and rotary evaporated under reduced pressure to obtain 2-bromo-4'-fluorodiphenyl sulfone. Yield 90%.

[0046] (2) Synthesis of intermediate [2-bromo-4'-phenothiazine diphenyl sulfone]

[0047]

[0048] Under the protection of a nitrogen atmosphere, 10 mmol of phenothiazine was added into a three-necked flask, and 20 mL of N,N-dimethylformamide was added and stirred to dissolve it. Add 10 mmol ...

Embodiment 2

[0053] (1) Synthesis of intermediate [2-fluoro-4'-fluorodiphenylsulfone]

[0054]

[0055] Put 10 mmol of 2-fluorobenzenesulfonyl chloride and 25 mmol of fluorobenzene into a three-necked flask, stir and dissolve under a nitrogen atmosphere, add 13 mmol of ferric chloride, and stir at 40°C for 70 minutes. 50 mL of 2M hydrochloric acid was added to terminate the reaction. It was extracted three times with appropriate amount of dichloromethane, and the obtained organic phase was extracted three times with pure water. The organic phase was dried by adding anhydrous sodium sulfate, filtered, and rotary evaporated under reduced pressure to obtain 2-fluoro-4'-fluorodiphenyl sulfone. Yield 90%.

[0056] (2) Synthesis of intermediate [2-fluoro-4'-phenothiazine diphenyl sulfone]

[0057]

[0058] Under the protection of a nitrogen atmosphere, 10 mmol of phenothiazine was added into a three-necked flask, and 20 mL of N,N-dimethylformamide was added and stirred to dissolve it. ...

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Abstract

The invention discloses a TADF material based on large steric hindrance space charge transfer and its synthesis method and application. It can first obtain a 2-substituted fluorinated or brominated intermediate, and then pass the corresponding boric acid through Sizuki In the reaction, the final product can be obtained through substitution reaction with the corresponding aromatic amine; or the corresponding borate intermediate can be obtained first, and then the final product can be obtained through Sizuki reaction with the corresponding brominated aromatic hydrocarbon. The synthesis process of the present invention is simple, the purification is easy, and the synthesized TADF light-emitting material has the characteristics of high luminous efficiency and adjustable luminous color, and can be used as a light-emitting layer to prepare organic electroluminescence with high efficiency, low cost and good stability device.

Description

technical field [0001] The invention relates to the field of new materials, in particular to a thermally activated delayed fluorescent material based on large steric hindrance space charge transfer, a synthesis method and its application as a light-emitting layer material in organic electroluminescent devices. [0002] technical background [0003] Organic light-emitting diodes (Organic Light-Emitting Devices, OLEDs) have been reported for more than 20 years, and have achieved rapid development in material development and device fabrication processes. OLED is used in the display screens of mobile phones, digital cameras, computers, etc., especially in the field of TV display technology. Large-size, transparent, and bendable OLED screens are the current development direction. However, at present, organic light-emitting diodes still have a series of shortcomings such as low luminous efficiency, short service life, poor stability and high production costs, and large-scale commer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12C07D209/86C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/86C07D417/12C09K2211/1037C09K2211/1029C09K2211/1014C09K2211/1007H10K85/657H10K85/6572H10K50/11
Inventor 杨湛毛竹赵娟陈晓洁杨志涌于涛郑世昭刘四委张艺池振国许家瑞
Owner SUN YAT SEN UNIV
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