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Organic electroluminescent compounds and organic light emitting diode using the same

A compound, electroluminescence technology, applied in the direction of organic chemistry, compounds of elements of Group 4/14 of the periodic table, luminescent materials, etc., can solve problems such as hindering power consumption, small improvement of operating voltage, deterioration and so on

Inactive Publication Date: 2010-06-09
GRACEL DISPLAY INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] It is particularly noteworthy that conventional electron-transporting materials show only small improvements in operating voltage compared to reported materials, or show a large decrease in device operating lifetime.
In addition, the material shows various adverse effects such as deviation of lifetime of the device for various colors and deterioration of thermal stability
To date, these adverse effects have prevented the achievement of goals such as reasonable power consumption and increased brightness, which have been problems in the manufacture of large-sized OLED panels.

Method used

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  • Organic electroluminescent compounds and organic light emitting diode using the same
  • Organic electroluminescent compounds and organic light emitting diode using the same
  • Organic electroluminescent compounds and organic light emitting diode using the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0110] [Preparation Example 1] Preparation of Compound (102)

[0111]

[0112] Preparation of compound (201)

[0113] Add 1,2-dibromobenzene (100.0 g, 423.9 mmol), 2-naphthaleneboronic acid (80.2 g, 466.3 mmol), toluene (1000 ml) and tetrakis(triphenylphosphine) palladium (Pd( PPh 3 ) 4 ) (24.5 g, 21.2 mmol), and the mixture was stirred under an argon atmosphere. Aqueous potassium carbonate solution (300 ml) was then added dropwise to the mixture, and the resulting mixture was heated under reflux with stirring for 4 hours. The reaction was quenched by adding distilled water (2000 mL), and the reaction mixture was extracted with ethyl acetate (1000 mL). The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (ethyl acetate:hexane=1:50) gave 1-bromo-2-(2-naphthyl)benzene (63.59 g, 224.7 mmol, yield: 53.0%).

[0114] 1-Bromo-2-(2-naphthyl)benzene (42.0 g, 148.5 mm...

preparation example 2

[0125] [Preparation Example 2] Preparation of Compound (103)

[0126]

[0127] Preparation of compound (206)

[0128] Add 1,2-dibromobenzene (100 g, 423.9 mmol), 2-(9,9′-dimethyl)fluoreneboronic acid (111.0 g, 466.3 mmol), toluene (1000 ml) and tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ) (24.5 g, 21.2 mmol), and the mixture was stirred under an argon atmosphere. Aqueous potassium carbonate solution (300 ml) was then added dropwise to the mixture, and the resulting mixture was heated under reflux with stirring for 4 hours. When the reaction was completed, distilled water (1500 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (800 mL). The obtained organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (ethyl acetate: hexane = 1:30) afforded the product, 1-bromo-2-(9,9'-dimethyl)fluorenylbenzene (75.52 g, 217.0 mmol, yield :...

preparation example 3

[0140] [Preparation Example 3] Preparation of Compound (110)

[0141]

[0142] Preparation of compound (211)

[0143] Add compound (210) (43.90 g, 92.62 mmol) and tetrahydrofuran (1000 ml) in a 500 ml round bottom flask, add n-BuLi (1.6M hexane solution) (55.57 ml, 138.9 ml) dropwise to the flask at -78°C Millimoles). The mixture was stirred at the same temperature for 1 hour, triphenylsilyl chloride (40.95 g, 138.9 mmol) was added dropwise to the reaction mixture, and the temperature was raised to room temperature. The reaction mixture was stirred for 12 hours, and when the reaction was complete, distilled water (1000 ml) was added thereto. The obtained organic extract was extracted with ethyl acetate (800 ml), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane:hexane=1:25) gave compound (211) (34.22 g, 52.33 mmol, yield: 56.5%).

[0144] Preparation of compound...

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PUM

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Abstract

The present invention relates to novel organic electroluminescent compounds and organic light emitting diodes comprising the same. Since the organic electrolumescent compounds according to the invention have good luminous efficiency and life property as an electroluminescent material, OLED's having very good operation lifetime can be produced.

Description

technical field [0001] The present invention relates to novel organic electroluminescent compounds and organic light-emitting diodes comprising the compounds. Background technique [0002] As modern society enters an information-oriented era, the importance of displays, which function as an interface between electronic information devices and humans, is increasing. As a novel flat display technology, OLED has been actively researched worldwide since its excellent display performance as a self-emitting device, and it is easy to manufacture because of its simple device mechanism, enabling the manufacture of ultra-thin and ultra-light monitor. [0003] OLED devices generally comprise a plurality of thin layers of organic compounds between a cathode and an anode composed of metal. Electrons and holes injected through the cathode and anode pass through the electron injection layer and the electron transport layer, respectively, and the hole injection layer and the hole transpor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
CPCC09K2211/1011C09K2211/1007H01L51/5048C09K2211/1014H01L51/0094C09K11/06H01L51/0058H10K85/626H10K85/40H10K50/14C07F7/0805C09K2211/188H10K50/00
Inventor 李美爱权赫柱赵英俊金奉玉金圣珉尹胜洙
Owner GRACEL DISPLAY INC
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