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Organic electroluminescent compound and organic electroluminescent device comprising the same

An electroluminescence device and electroluminescence technology, which are applied in the fields of organic chemistry, light-emitting materials, chemical instruments and methods, etc., can solve the problem of high hole mobility, low glass transition temperature, and reduced hole-electron charge balance quantum yield. etc., to achieve the effect of high current efficiency

Inactive Publication Date: 2016-01-20
ROHM & HAAS ELECTRONIC MATERIALS LLC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although these materials provide good light emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur in vacuum during the high temperature deposition process, which leads to poor lifetime
Therefore, there is no advantage regarding power efficiency (lm / W)
(3) In addition, the lifetime of organic EL devices is short, and improvement in luminous efficiency is still required
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 and organic electroluminescent device comprising the same
  • Organic electroluminescent compound and organic electroluminescent device comprising the same
  • Organic electroluminescent compound and organic electroluminescent device comprising the same

Examples

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Effect test

example 1

[0105] Example 1: Preparation of Compound C-1

[0106]

[0107] Preparation of compound 1-1

[0108] In 5H-benzofuro[3,2-c]carbazole (30g, 117mmol), 4-bromo-1-fluoro-2-nitrobenzene (26g, 117mmol), cesium carbonate (46g, 140mmol) and After 300 mL of dimethyl sulfoxide was introduced into the reaction vessel, the mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed several times with water, and dried over anhydrous magnesium sulfate. The mixture was distilled under reduced pressure, and purified by column chromatography to obtain Compound 1-1 (45 g, 85%).

[0109] Preparation of Compound 1-2

[0110] After compound 1-1 (30 g, 66 mmol), tin(II) chloride hydrate (44.4 g, 200 mmol), and 700 mL of ethyl acetate were introduced into the reaction vessel, the mixture was refluxed for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with water several times, and dried over anhydrou...

example 2

[0116] Example 2: Preparation of Compound C-4

[0117]

[0118] Preparation of compound 2-1

[0119] In 5H-benzofuro[3,2-c]carbazole (30g, 117mmol), 1-bromo-3,5-dichlorobenzene (40g, 176mmol), copper(I) iodide (11g, 59mmol ), ethylenediamine (15 mL, 234 mmol), potassium phosphate (50 g, 234 mmol), and 600 mL of toluene were introduced into the reaction vessel, and the mixture was refluxed overnight. The mixture was diluted with ethyl acetate, washed several times with water, and dried over anhydrous magnesium sulfate. The mixture was distilled under reduced pressure, and purified by column chromatography to obtain compound 2-1 (28 g, 60%).

[0120] Preparation of compound 2-2

[0121] In compound 2-1 (14.3g, 35.5mmol), diphenylamine (6g, 35.5mmol), palladium (II) acetate (0.16g, 0.71mmol), S-Phos (2-bicyclic phosphino-2', After 6'-dimethoxyphenyl) (0.58 g, 1.42 mmol), sodium tert-butoxide (4 g, 43 mmol) and 350 mL of o-xylene were introduced into the reaction vess...

example 3

[0125] Example 3: Preparation of Compound C-12

[0126]

[0127] Compound 2-1 (7.5g, 18.5mmol), 4-(diphenylamino)phenylboronic acid (12.3g, 42.5mmol), palladium (II) acetate (0.35g, 1.5mmol), S-Phos ( 2-bicyclic phosphino-2',6'-dimethoxyphenyl) (0.9 g, 2.2 mmol), potassium phosphate (12 g, 55.5 mmol), 100 mL of toluene, 25 mL of 1,4-dioxane and 25 mL of distilled water After introduction into the reaction vessel, the mixture was refluxed overnight. After completing the reaction, the mixture was washed with distilled water, extracted with ethyl acetate, and dried over magnesium sulfate. After removing the solvent by a rotary evaporator, the mixture was purified by column chromatography to obtain compound C-12 (9.4 g, 62%).

[0128] Physical properties: Melting point 178°C, UV354nm (in toluene), PL396nm (in toluene), molecular weight 821.59[M+1]

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Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device showing excellent current efficiency can be provided.

Description

technical field [0001] The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the compound. Background technique [0002] An electroluminescent (EL) device is a self-luminous device that is advantageous in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The organic EL device was originally developed by Eastman Kodak by using an aromatic diamine small molecule and an aluminum complex as materials for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987]. [0003] The most important factor determining the luminous efficiency in an organic EL device is the luminescent material. Hitherto, fluorescent materials have been widely used as light-emitting materials. However, in view of the mechanism of electroluminescence, phosphorescent light-emitting materials have been extensively studied because phosphorescent materials theoretically enhance luminous eff...

Claims

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Application Information

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IPC IPC(8): C07D491/048C07D495/04C07D487/04C07D409/10C09K11/06H01L51/54H01L27/32
CPCC07D409/10C07D487/04C07D491/048C07D495/04C09K11/06H10K85/636H10K85/654H10K85/657H10K85/342H10K50/15H10K50/11H10K2101/10C07D491/04H10K85/649H10K85/653H10K85/655H10K85/631
Inventor S-J·杨H-C·安T-J·李C-S·金Y-J·曹K-J·李
Owner ROHM & HAAS ELECTRONIC MATERIALS LLC
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