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Organic electroluminescent compound, organic electroluminescent material, and organic electroluminescent device comprising same

A technology of luminescence and compounds, which is applied in luminescent materials, organic chemistry, organic semiconductor devices, etc., can solve the problems of low glass transition temperature, no advantage in power efficiency, and shortened device life.

Active Publication Date: 2022-02-08
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although these materials provide good light-emitting properties, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade in vacuum during the high-temperature deposition process, and the lifetime of the device may be limited. shorten
Therefore, there is no advantage in terms of power efficiency (lm / W)
(3) In addition, the service life of organic electroluminescent devices is short, and the luminous efficiency still needs to be improved
Thermal stress significantly reduces the service life of the device
In addition, since the organic material used for the hole injection layer has extremely high hole mobility, the hole-electron charge balance may be broken and the quantum yield (cd / A) may decrease

Method used

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  • Organic electroluminescent compound, organic electroluminescent material, and organic electroluminescent device comprising same
  • Organic electroluminescent compound, organic electroluminescent material, and organic electroluminescent device comprising same
  • Organic electroluminescent compound, organic electroluminescent material, and organic electroluminescent device comprising same

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0091] Example 1 prepares compound C-73

[0092]

[0093] 1) Preparation of compound 1-1

[0094] In 20g compound A (81.2mmol), 26.8g two (pinacolate) diborane (105mmol), 2.8g two (triphenylphosphine) dichloride palladium (II) (4mmol), 16g potassium acetate ( 162 mmol) and 400 mL of 1,4-dioxane were introduced into the reaction vessel, and the mixture was stirred overnight at 140°C. After the reaction was completed, the reaction product was cooled to room temperature, and then extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. After that, the resulting product was purified by column chromatography to obtain 15.4 g of Compound 1-1 (77%).

[0095] 2) Preparation of compound 1-2

[0096] In 14g compound 1-1 (56.6mmol), 6.1mL 2-bromoaniline (54mmol), 2.6g tetrakis (triphenylphosphine) palladium (2.3mmol), 19.6g potassium carbonate (142mmol), 280mL toluene, 70mL ethanol After ...

example 2

[0106] Example 2: Preparation of Compound C-7

[0107]

[0108] After 3.1 g of compound 1-4 (9.3 mmol) prepared by the same method as in Example 1, 2.6 g of 3-bromo-1,1'-biphenyl (11.2 mmol), 256 mg of tris(dibenzylideneacetone) After dipalladium(0) (0.28 mmol), 227 mg of tris(o-tolyl)phosphine (0.74 mmol), 1.8 g of sodium tert-butoxide (18.6 mmol) and 93 mL of toluene were introduced into the reaction vessel, the mixture was stirred at 120 °C 3 hours. After the reaction was completed, the reaction product was cooled to room temperature, and then extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. After that, the resulting product was purified by column chromatography to obtain 2.8 g of Compound C-7 (62%).

[0109] MW UV PL M.P. C-7 484.6 307nm 395nm 274℃

example 3

[0110] Example 3: Preparation of Compound C-91

[0111]

[0112] After 3.5 g of compound 1-4 (10.5 mmol) prepared by the same method as in Example 1, 4.9 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5- Triazine (12.6mmol), 385mg tris(dibenzylideneacetone) dipalladium (0) (0.4mmol), 256mg tris(o-tolyl)phosphine (0.8mmol), 2.0g sodium tert-butoxide (21mmol) and 90mL After introducing toluene into the reaction vessel, the mixture was stirred at 130°C for 2 hours. After the reaction was completed, the reaction product was cooled to room temperature, and the solvent was removed with a rotary evaporator. After that, the resulting product was purified by column chromatography to obtain 2.4 g of Compound C-91 (36%).

[0113] MW UV PL M.P. C-91 640.10 308nm 428nm 198℃

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Abstract

The present disclosure relates to organic electroluminescent compounds, organic electroluminescent materials, and organic electroluminescent devices comprising the same. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having a low driving voltage and / or excellent current and / or power efficiency can be provided.

Description

technical field [0001] The present disclosure relates to organic electroluminescent compounds, organic electroluminescent materials, and organic electroluminescent devices comprising the same. Background technique [0002] Among display devices, an electroluminescent device (EL device) is a self-luminous display device, which has advantages in providing a wider viewing angle, a higher contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light emitting layer [Appl. Phys. Lett .) 51, 913, 1987]. [0003] The most important factor determining the luminous efficiency in an organic electroluminescent device is the luminescent material. Fluorescent materials have been widely used as light-emitting materials so far. However, from the viewpoint of electroluminescence mechanism, phosphorescent light emitting materials have been ext...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06C07D498/06C07D513/06C09K11/06H01L51/54
CPCC07D487/06C07D498/06C07D513/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C07D487/04H10K85/653H10K85/615H10K85/631H10K85/636H10K85/633H10K85/654H10K85/6576H10K85/657H10K85/6572H10K85/6574H10K85/342H10K50/11H10K50/166H10K50/165H10K50/18H10K2101/10H10K2101/90C07D209/82C07D307/91C07D333/76C09K2211/1018
Inventor 文斗铉梁正恩
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC