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An organic electroluminescent material and an organic electroluminescent device comprising the same

An electroluminescent material and luminescent technology, applied in luminescent materials, electric solid devices, organic chemistry, etc., can solve the problems of easy crystallization and performance degradation of light-emitting devices, and achieve optimal hole transport rate adjustment and high luminous efficiency and service life, the effect of low driving voltage

Active Publication Date: 2020-06-30
SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the commonly used hole transport material is NPD. Although NPD has excellent hole transport properties, its glass transition temperature (Tg) is only 96°C, which leads to easy crystallization of organic electroluminescent devices at high temperatures. thereby reducing performance

Method used

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  • An organic electroluminescent material and an organic electroluminescent device comprising the same
  • An organic electroluminescent material and an organic electroluminescent device comprising the same
  • An organic electroluminescent material and an organic electroluminescent device comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0041] Synthesis of compound 1

[0042]

[0043] Add 1-adamantanol (50.0g, 328.4mmol), bromobenzene (51.6g, 328.4mmol), dichloromethane (500mL) into a round bottom flask, cool down to -5-0°C under nitrogen protection, and dropwise add Trifluoromethanesulfonic acid (73.9g, 492.6mmol), keep stirring for 3h; add deionized water (300mL) to the reaction solution and wash to pH=7, add dichloromethane (100mL) for extraction, combine the organic phases, use Dry over magnesium sulfate, filter, and remove the solvent under reduced pressure; the resulting crude product is purified by silica gel column chromatography using n-heptane as the mobile phase to obtain white solid intermediate I-A-1 (53.1 g, 55.4%).

[0044]

[0045] Intermediate I-A-1 (7.0g, 24.04mmol), aniline (2.69g, 28.84mmol), tris(dibenzylideneacetone) dipalladium (0.22g, 0.24mmol), 2-dicyclohexylphosphorus-2' , 4',6'-triisopropylbiphenyl (0.23g, 0.48mmol) and sodium tert-butoxide (3.46g, 36.05mmol) were added to to...

Synthetic example 2

[0051] Synthesis of Compound 2

[0052]

[0053] N-phenyl-4-benzidine (5.00g, 20.38mmol), 4-bromo-4'-iodobiphenyl (9.15g, 25.48mmol), tris(dibenzylideneacetone)dipalladium (0.19g, 0.20mmol), tri-tert-butylphosphine (0.08g, 0.41mmol) and sodium tert-butoxide (2.94g, 30.57mmol) were added to toluene (80mL), heated to 108°C under nitrogen protection, stirred for 16h; then cooled to room temperature , the reaction solution was washed with water and dried by adding magnesium sulfate. After filtration, the filtrate was desolventized under reduced pressure; using n-heptane as the mobile phase for silica gel column chromatography to obtain intermediate II-B (5.55g, 57.16%).

[0054]

[0055] Intermediate I-A (4.70g, 15.49mmol), intermediate II-B (5.55g, 15.49mmol), tris(dibenzylideneacetone)dipalladium (0.14g, 0.15mmol), 2 -Dicyclohexylphosphonium-2', 6'-dimethoxybiphenyl (0.13g, 0.31mmol) and sodium tert-butoxide (2.23g, 23.23mmol) were added to toluene (50mL), and heated to 1...

Synthetic example 3

[0057] Synthesis of Compound 3

[0058]

[0059] 3-Bromodibenzofuran (10.0g, 40.47mmol), aniline (4.15g, 44.52mmol), tris(dibenzylideneacetone) dipalladium (0.37g, 0.40mmol), 2-dicyclohexylphosphine- 2,4,6-Triisopropylbiphenyl (0.39g, 0.81mmol) and sodium tert-butoxide (5.84g, 60.71mmol) were added to toluene (100mL), heated to 108°C under nitrogen protection, and stirred for 1h; then Cool to room temperature, wash the reaction solution with water, add magnesium sulfate to dry, filter and pass the filtrate through a short silica gel column, and remove the solvent after passing through the column under reduced pressure; use dichloromethane / n-heptane system to recrystallize and purify the crude product to obtain a gray solid Intermediate II-C-1 (8.2 g, 78.17%).

[0060]

[0061] 3-Bromo-4'chloro-1,1'-biphenyl (8.00g, 29.90mmol), intermediate II-C-1 (5.17g, 19.93mmol), tris(dibenzylideneacetone)dipalladium ( 0.18g, 0.20mmol), tri-tert-butylphosphine (0.10g, 0.40mmol) and ...

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Abstract

The invention provides an organic electroluminescent material and an organic light-emitting device comprising the organic electroluminescent material. The structural formula of the organic electroluminescent material is: compared with the monoamine structure containing an adamantyl group, the present invention contains The diamine structure has higher HOMO energy and hole mobility, which can show higher efficiency and lifetime than monoamine materials. The organic light-emitting device comprising the organic electroluminescent material has lower driving voltage, higher luminous efficiency and service life.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescence material and an organic electroluminescence device comprising the material. Background technique [0002] In recent years, an organic electroluminescent device (OLED, Organic electroluminescent device) as a new generation display technology has gradually entered people's field of vision. A common organic electroluminescent device is composed of an anode, a cathode, and more than one organic layer arranged between the cathode and the anode. When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the light-emitting layer, and the holes on the anode side also move to the light-emitting layer. The two combine to form excitons in the light-emitting layer. It releases energy in the excited state, and emits light...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/54C07C211/58C07D307/91C07D209/86C07C211/61C07D333/76C07D209/88C09K11/06H01L51/54H01L51/50
CPCC07C211/54C07C211/58C07D307/91C07D209/86C07C211/61C07D333/76C07D209/88C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/615H10K85/631H10K85/636H10K85/626H10K85/633H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/181C07D409/12C07C2603/18C07C2603/74H10K50/18
Inventor 马天天聂齐齐冯震李红燕沙荀姗孙占义王亚龙
Owner SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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