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Novel organic electroluminescent compounds and organic electroluminescent device using the same

A technology of luminescence and compounds, applied in the field of organic electroluminescent devices, can solve the problems of reduced quantum yield and reduced device operating life

Inactive Publication Date: 2012-05-09
ROHM & HAAS ELECTRONIC MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thermal stress greatly reduces the operating lifetime of the device
In addition, since the organic material used for the hole injection layer has very high hole mobility, the hole-electron charge balance may be disrupted and the quantum yield (cd / A) may decrease

Method used

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  • Novel organic electroluminescent compounds and organic electroluminescent device using the same
  • Novel organic electroluminescent compounds and organic electroluminescent device using the same
  • Novel organic electroluminescent compounds and organic electroluminescent device using the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0065] [Preparation Example 1] Preparation of Compound 4

[0066]

[0067] Preparation of Compound A

[0068] 2-Naphthol (20.0g, 138.8mmol), NaHSO 3 (28.8g, 274.4mmol), distilled water (160mL) and 4-bromophenylhydrazine (31.2mL, 164.4mmol) were heated at 120°C. After 12 hours, distilled water was added and the resulting solid was filtered under reduced pressure. The solid thus obtained was added to aqueous HCl and heated to 100°C. One hour later, after extraction with dichloromethane, the product was washed with distilled water and aqueous NaOH. Column separation gave compound A (9.2 g, 31.0 mmol, 22.4%).

[0069] Preparation of Compound B

[0070] Compound A (9.2g, 31.0mmol), Cu (2.0g, 31.0mmol), 18-crown-6 (0.4g, 1.6mmol), K 2 CO 3 (12.8 g, 93.2 mmol) and 1,2-dichlorobenzene (100 mL) were mixed and stirred under reflux at 180° C. for 12 hours. After cooling to room temperature and distillation under reduced pressure, the product was extracted with dichloromethane ...

Embodiment 1

[0087] [Example 1] Manufacturing OLED devices using the organic electroluminescent compound of the present invention

[0088] OLED devices are fabricated using the organic electroluminescent compounds of the present invention.

[0089] First, the transparent electrode ITO film (15Ω / □) prepared from a glass substrate for OLED (Samsung Corning) was ultrasonically cleaned with trichlorethylene, acetone, ethanol and distilled water in sequence, and stored in isopropanol for future use.

[0090] Next, the ITO substrate was loaded into a substrate holder of a vacuum deposition apparatus. After adding 4,4',4"-three (N, N-(2-naphthyl)-phenylamino) triphenylamine (2-TNATA) in the chamber (cell) of vacuum deposition equipment, the pressure in the chamber dropped to 10 -6 support. Subsequently, 2-TNATA was evaporated by applying a current to the chamber to form a hole injection layer with a thickness of 60 nm on the ITO substrate.

[0091] Thereafter, after compound 1 was added in an...

Embodiment 2

[0106] [Example 2] Preparation of OLED devices using the organic electroluminescent compound of the present invention

[0107] Using the same method as in Example 1, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus. After injecting compound 12 into the chamber of vacuum deposition equipment, the pressure in the chamber dropped to 10 -6 support. Subsequently, a current was applied in the chamber to evaporate compound 12 to form a hole injection layer with a thickness of 60 nm on the ITO substrate.

[0108] Next, add N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) into another chamber of the vacuum deposition equipment, and apply a current in the chamber NPB was evaporated to form a hole transport layer with a thickness of 20 nm on the hole injection layer.

[0109]

[0110] Remaining process is identical with embodiment 1.

[0111] The fluorescence efficiency of the OLED device that embodiment 2 and comparative example 1 manu...

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Abstract

Disclosed are a novel organic electroluminescent compound and an organic electroluminescent device including the same. When included in a hole injection layer or a hole transport layer of an organic electroluminescent device, the disclosed organic electroluminescent compound can improve luminous efficiency while lowering driving voltage of the device.

Description

technical field [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the compound. The organic electroluminescent compound of the present invention may be included in a hole-transport layer or a hole-injection layer of an organic electroluminescent device. Background technique [0002] Among display devices, as a self-emissive display device, an electroluminescent (EL) device has the advantages of providing a wide viewing angle, excellent contrast and fast response rate. In 1987, Eastman Kodak first developed an organic EL device using a complex of low molecular weight aromatic diamine and aluminum as a material for forming an electroluminescent layer. (Applied Physics Letters, 1987, Issue 51, Page 913). [0003] In an organic EL device, when an electric charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), electrons...

Claims

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Application Information

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IPC IPC(8): C09K11/06
CPCH01L51/006H01L51/0085H01L51/0077H01L51/5048H01L51/0081H01L51/0059H01L51/5088H10K85/631H10K85/633H10K85/30H10K85/324H10K85/342H10K50/14H10K50/17C09K11/06
Inventor 金荣佶赵英俊权赫柱金奉玉金圣珉尹胜洙
Owner ROHM & HAAS ELECTRONIC MATERIALS LLC
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