Thermal activation delay fluorescent material and organic light-emitting display device comprising same

A technology of thermally activated delayed and fluorescent materials, applied in the fields of luminescent materials, organic chemistry, silicon organic compounds, etc., can solve the problems of single type of materials, unable to meet the development needs of OLED devices, etc., and achieve the effect of improving luminous efficiency and good stability

Active Publication Date: 2019-01-04
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still relatively little research on thermally activated delayed fluorescence materials, and the types of materials are still single, which cannot meet the development needs of OLED devices.

Method used

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  • Thermal activation delay fluorescent material and organic light-emitting display device comprising same
  • Thermal activation delay fluorescent material and organic light-emitting display device comprising same
  • Thermal activation delay fluorescent material and organic light-emitting display device comprising same

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0096] Compound P5 is synthesized according to the following route:

[0097]

[0098]Put S1 (10.5mmol), S2 (10mmol), (dibenzylideneacetone) dipalladium (0) (0.05mmol), sodium tert-butoxide (14mmol), tert-butylphosphine (0.2mmol) into a 100mL three-necked flask , while stirring, while rapidly repeating degassing and nitrogen replacement 3 times, 20 mL of toluene was added through a syringe. The mixture was heated to reflux for 12 hours under a stream of nitrogen. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain intermediate P5 (8.2 mmol, yield 82%).

[0099] Carry out elemental analysis structure to P5 (molecular formula C 28 h 29 NO 2 S): Calculated: C, 75.81; H, 6.59; N, 3.16; O, 7.21; S, 7.23; Found: C, 75.83; H, 6.61; N...

preparation example 2

[0101] Compound P8 is synthesized according to the following route:

[0102]

[0103] Specific steps: S3 (8.5mmol), S4 (8mmol), (dibenzylideneacetone) dipalladium (0) (0.06mmol), sodium tert-butoxide (12mmol), tert-butylphosphine (0.3mmol) into 100mL In the three-necked flask, while stirring, degassing and nitrogen replacement were repeated three times rapidly, and 20 mL of toluene was added through a syringe. The mixture was heated to reflux for 12 hours under a stream of nitrogen. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain product P8 (5.76 mmol, yield 72%).

[0104] Carry out elemental analysis structure to P8 (molecular formula C 39 h 26 N 2 o 2 S): Calculated: C, 79.84; H, 4.47; N, 4.77; O, 5.45; S, 5.47; Found:...

preparation example 3

[0106] Compound P14 is synthesized according to the following route:

[0107]

[0108] Specific steps: put S5 (6.0mmol), S6 (6.3mmol), (dibenzylideneacetone) dipalladium (0) (0.05mmol), sodium tert-butoxide (10mmol), tert-butylphosphine (0.25mmol) into In a 100mL three-neck flask, while stirring, degassing and nitrogen replacement were repeated 3 times rapidly, and 30mL of toluene was added through a syringe. The mixture was heated to reflux for 12 hours under a stream of nitrogen. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain the target product P14 (4.56 mmol, yield 76%).

[0109] Carry out elemental analysis structure to P14 (molecular formula C 32 h 23 NO 2 SSi): Calculated: C, 74.82; H, 4.51; N, 2.73; O, 6.23; S, 6....

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PUM

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Abstract

The invention relates to a thermal activation delay fluorescent material and an organic light-emitting display device comprising the same. The thermal activation delay fluorescent material is any oneor a combination of at least two of compounds with the structure in a formula (I). The organic light-emitting display device comprises an anode, a cathode and at least one organic film layer positioned between the anode and the cathode; and the organic film layer comprises a light-emitting layer as well as at least one or a combination of at least two of a cavity transportation layer, a cavity injection layer, an electron blocking layer, a cavity blocking layer, an electron transmission layer and an electron injection layer. In the thermal activation delay fluorescent material provided by theinvention, delta Est is less than or equal to 0.30 eV, and even the delta Est is less than or equal to 0.15 eV, so that the organic light-emitting display device comprising the thermal activation delay fluorescent material has high light-emitting efficiency.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a heat-activated delayed fluorescent material and an organic light-emitting display device comprising the same. Background technique [0002] Organic light-emitting diode (OLED) refers to a diode in which organic light-emitting materials emit light under the action of current or electric field, which can directly convert electrical energy into light energy. OLED technology has many advantages such as full solid state, active light emission, high contrast, ultra-thin, flexible display, low power consumption, wide viewing angle, fast response speed, wide operating temperature range, and easy realization of 3D display. Ordinary display” will become the most promising new display technology in the future. [0003] Of course, behind the rapid advancement of OLED technology, organic light-emitting materials play an important role. Organic light-emitting m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C07D471/10C07D401/14C07D409/14C07D495/04C07D413/14C07D417/14C07D333/54C07D491/048C07D471/04C07D487/04C07F7/08C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D333/54C07D401/14C07D409/04C07D409/14C07D413/14C07D417/14C07D471/04C07D471/10C07D487/04C07D491/048C07D495/04C07F7/0816C07F7/083C09K2211/1092C09K2211/1088C09K2211/1044C09K2211/104C09K2211/1037C09K2211/1033C09K2211/1029C09K2211/1007H10K85/6576H10K85/6572H10K85/657H10K85/40H10K50/11
Inventor 高威张磊朱晴牛晶华安平
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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