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Organic compound, light emitting diode including same and organic light emitting diode display

A technology of organic compounds and light-emitting diodes, applied in the direction of diodes, organic chemistry, electroluminescent light sources, etc., can solve the problems of reduced LED life, reduced injection efficiency, and deteriorated LED characteristics

Active Publication Date: 2018-06-29
LG DISPLAY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the injection efficiency of electrons generated at the interface between the P-type charge generation layer and the hole injection layer or the hole transport layer is injected into the N-type charge generation layer decreases.
Since electrons are not injected from the N-type charge generation layer into the adjacent electron transport layer, the characteristics of the LED are deteriorated, and the lifetime of the LED is reduced

Method used

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  • Organic compound, light emitting diode including same and organic light emitting diode display
  • Organic compound, light emitting diode including same and organic light emitting diode display
  • Organic compound, light emitting diode including same and organic light emitting diode display

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0154] Synthesis Example 1: Synthesis of Compound EN-016

[0155]

[0156] By adding 4,4,5,5-tetramethyl-2-(1-(phenanthrene-10-yl)naphthalene-4-yl)-1,3,2-dioxaborolane ( 6.0g, 13.94mmol), 2-bromo-9-phenyl-1,10-phenanthroline (4.20g, 12.57mmol), tetrakis-triphenylphosphine palladium (0) (Pd(PPh 3 ) 4 ) (0.50 g, 0.70 mmol), 4M potassium carbonate aqueous solution (10 mL), toluene 30 mL, and ethanol (EtOH) 10 mL were dissolved to form a mixture, and the mixture was refluxed and stirred for 12 hours. After the reaction was complete, H was added to the mixture 2 O 50 mL, the mixture was stirred for 3 hours and vacuum filtered. After the mixture was separated by column chromatography using dichloromethane (MC) and n-hexane as eluents, the mixture was recrystallized using MC to obtain compound EN-016 (6.25 g, migration number 80.3%).

Synthetic example 2

[0160] Synthesis Example 2: Synthesis of Compound EN-145

[0161]

[0162] By adding 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9-phenyl- 1,10-phenanthroline (5.0g, 10.91mmol), 4-(4-bromophenyl)-2,6-diphenylpyrimidine (4.80g, 12.40mmol), tetrakis-triphenylphosphine palladium (0)(Pd(PPh 3 ) 4 ) (0.63g, 0.55mmol), 4M potassium carbonate aqueous solution (10mL), toluene 30mL, ethanol (EtOH) 10mL were dissolved to form a mixture, the mixture was refluxed and stirred for 12 hours. After the reaction was complete, H was added to the mixture 2 O 50 mL, the mixture was stirred for 3 hours and vacuum filtered. After the mixture was separated by column chromatography using dichloromethane (MC) and n-hexane as eluents, the mixture was recrystallized using MC to obtain compound EN-145 (5.01 g, migration number 72.3%).

Synthetic example 3

[0166] Synthesis Example 3: Synthesis of Compound EN-160

[0167]

[0168] By adding 2-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-4-yl)-9- Phenyl-1,10-phenanthroline (5.5g, 10.82mmol), 4-(4-bromophenyl)-2,6-diphenylpyrimidine (4.50g, 11.63mmol), tetrakis-triphenyl Phosphine palladium (0) (Pd (PPh 3 ) 4 ) (0.63g, 0.54mmol), 4M potassium carbonate aqueous solution (10mL), toluene 30mL, ethanol (EtOH) 10mL were dissolved to form a mixture, the mixture was refluxed and stirred for 12 hours. After the reaction was complete, H was added to the mixture 2 O 50 mL, the mixture was stirred for 3 hours and vacuum filtered. After the mixture was separated by column chromatography using dichloromethane (MC) and n-hexane as eluents, the mixture was recrystallized using MC to obtain compound EN-160 (5.03 g, migration number 72.8%).

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Abstract

The present disclosure relates to an organic compound, a light emitting diode, and an organic light emitting diode display device using the same. The organic compound is represented by a following chemical formula 1. This organic compound has the advantages in the electron transmitting property and the thermal stability and forms a stable gap state with an alkali metal and an alkali earth metal. The driving voltage of the light emitting diode is reduced and the emission efficiency and the lifetime of the light emitting diode are improved by applying the organic compound to the charge generation layer and / or the electron transporting layer of the light emitting diode of the tandem structure.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of Korean Patent Application No. 10-2016-0168918 filed in the Korean Intellectual Property Office on December 12, 2016, which is incorporated herein by reference in its entirety. technical field [0003] The present disclosure relates to an organic compound, and more particularly, to an organic compound having improved driving voltage and luminous efficiency, and a light emitting diode and an organic light emitting diode display device including the organic compound. Background technique [0004] As display devices expand, demand for flat panel displays with smaller footprints increases. Among various flat panel displays, organic light emitting diode (OLED) display devices including light emitting diodes (LEDs), which may be referred to as organic electroluminescent display (OELD) devices, have been the subject of recent research. [0005] An LED is an element in which holes and ele...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06H01L51/50H01L51/52H01L51/54H05B44/00
CPCC07D471/04C09K11/06C09K2211/1011C09K2211/1007C09K2211/1059C09K2211/1044H10K85/624H10K85/622H10K85/626H10K85/615H10K85/6572H10K50/16H10K50/19C07D401/14H10K85/654H10K59/38H10K59/123H10K59/1213H10K71/30H10K50/131H10K50/17H05B45/60H10K50/171H10K59/32H10K85/111H10K50/125
Inventor 申智徹朱性壎刘璇根尹丞希
Owner LG DISPLAY CO LTD
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