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Thermally activated delayed fluorescence material and organic light-emitting device

A technology of organic light-emitting devices and thermal activation delay, which is applied in the fields of light-emitting materials, organic chemistry, and electric solid-state devices. It can solve the problems of short life and scarcity of materials, and achieve high glass transition temperature, low driving voltage, and high thermal stability. Effect

Pending Publication Date: 2020-07-24
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the TADF materials constructed by this method still encounter many problems. Materials with high efficiency are still relatively scarce. The materials show high efficiency roll-off in devices, and their lifespan is short, which needs to be improved from the basis of molecular construction.

Method used

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  • Thermally activated delayed fluorescence material and organic light-emitting device
  • Thermally activated delayed fluorescence material and organic light-emitting device
  • Thermally activated delayed fluorescence material and organic light-emitting device

Examples

Experimental program
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Effect test

preparation example 1

[0237] Synthesis of the following compound 1

[0238]

[0239] Under nitrogen protection, 9-fluorenone-1-boronic acid (5.0g, 22.32mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.98g, 22.32mmol), Tetrakis(triphenylphosphine)palladium (773.39mg, 0.67mmol) and anhydrous potassium carbonate (6.16g, 44.64mmol) were placed in a 250ml round bottom flask, and 90ml of tetrahydrofuran and 22ml of distilled water were added. The above mixture was heated to reflux for 24 hours. After the reaction was completed, the temperature was lowered to room temperature, filtered with suction, washed with a large amount of distilled water, and purified by recrystallization with dichloromethane / ethanol to obtain intermediate 1 (7.89g, 19.20mmol yield about 86%), which was dried for later use. Under the protection of nitrogen, put 2-bromo-N-methyl-N-phenylaniline (5.03g, 19.20mmol) in a 250ml two-necked bottle, add 77ml of anhydrous tetrahydrofuran to dissolve, and then place it at minus 78 degrees...

preparation example 2

[0241] Synthesis of the following compound 2

[0242]

[0243] Under the protection of nitrogen, put 2-bromotriphenylamine (6.22g, 19.20mmol) in a 250ml two-necked bottle, add 77ml of anhydrous tetrahydrofuran to dissolve, then place it at minus 78 degrees Celsius, and add 2.4M concentration of n- Butyllithium solution (8.80ml, 21.12mmol) was stirred at minus 78 degrees Celsius for 1 hour, then Intermediate 1 (7.89g, 19.20mmol) was added, stirred overnight, and then quenched by adding 20ml of distilled water. Remove tetrahydrofuran from the reaction solution under reduced pressure, add 40ml of dichloromethane to extract 3 times, remove the dichloromethane under reduced pressure, add ethanol for recrystallization, place the solid obtained after suction filtration and drying in a 250ml flask, add 100ml of acetic acid and stir for 10 Minutes later, 3ml of concentrated hydrochloric acid was added and heated to reflux at 110°C for 3 hours. After the reaction was completed, the...

preparation example 3

[0245] Synthesis of the following compound 3

[0246]

[0247] Under nitrogen protection, 9-fluorenone-1-boronic acid (5.0g, 22.32mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (8.66 g, 22.32mmol), tetrakis(triphenylphosphine) palladium (773.39mg, 0.67mmol), anhydrous potassium carbonate (6.16g, 44.64mmol) were placed in a 250ml round bottom flask, and 90ml tetrahydrofuran and 22ml distilled water were added . The above mixture was heated to reflux for 24 hours. After the reaction was completed, the temperature was lowered to room temperature, filtered with suction, washed with a large amount of distilled water, and purified by recrystallization with dichloromethane / ethanol to obtain intermediate 2 (8.70 g, yield about 80%), which was dried for later use. Under the protection of nitrogen, put 2-bromo-triphenylamine (5.79g, 17.86mmol) in a 250ml two-necked bottle, add 77ml of anhydrous tetrahydrofuran to dissolve, then place it at minus 78 degrees Celsius, and add 2...

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Abstract

The invention relates to a thermally activated delayed fluorescence material and an organic light-emitting device. The thermally activated delayed fluorescence material comprises a compound represented by the general formula (1) shown in the specification, wherein R0, R1, R2 and R3 are each independently selected from hydrogen, deuterium, halogen groups, or any one of substituted or unsubstitutedC6-C30 aryl groups and C1-C20 fatty groups, R is selected from any one of substituted or unsubstituted C1-C10 aliphatic groups, C6-C30 aryl groups and C4-C30 heteroaryl groups, G is selected from anyone of a direct bond, or a substituted or unsubstituted arylene group of C6-C30, and a heteroarylene group of C4-C30; and A is a group having an electron-deficient property. The main functional elements of the thermally activated delayed fluorescence material are close in space, can realize a space nonconjugated charge transfer effect, have high thermal stability, high glass transition temperatureand excellent luminescence property, and can be used for an organic light-emitting device with a high effect.

Description

technical field [0001] The invention relates to a thermally activated delayed fluorescent material and an organic light-emitting device, belonging to the technical field of organic light-emitting. Background technique [0002] Organic Light Emitting Diode (OLED) is a current-driven light-emitting device that uses organic materials as active materials. Specifically, organic semiconductor materials and organic light-emitting materials are driven by electric fields through carrier injection and Composite technology that leads to luminescence. Unlike inorganic materials, organic materials have the characteristics of low synthesis cost, adjustable function, flexibility, and good film-forming properties. Moreover, devices based on organic materials are generally simple in fabrication process, easy to be prepared in large areas, and are environmentally friendly, and can adopt thin-film preparation methods with low operating temperature, so they have the advantages of low fabricati...

Claims

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Application Information

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IPC IPC(8): C07D221/20C07D401/04C07D401/10C07D401/14C07D405/04C07D409/04C07D409/14C07D411/04C07D411/14C07D417/04C07D417/10C07D471/06C07D471/14C07F5/02C07F9/576C07F9/6558C07F9/6568C07F9/6578C09K11/06H01L51/54H01L51/50
CPCC07D221/20C07D401/14C07D405/04C07D409/04C07D411/04C07D411/14C07D401/04C07D401/10C07D409/14C07D471/14C07D417/04C07D417/10C07F5/02C07D471/06C07F9/6578C07F9/65685C07F9/5765C07F9/65586C09K11/06C09K2211/1029C09K2211/1011C09K2211/1092C09K2211/1088C09K2211/1044C09K2211/1055C09K2211/1074C09K2211/1096C09K2211/1059C09K2211/1051H10K85/653H10K85/655H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/657H10K50/121H10K85/6572H10K50/11
Inventor 蒋佐权廖良生屈扬坤李虹成
Owner SUZHOU UNIV
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