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Novel organic electroluminescent compounds and organic electroluminescent device using the same

An electroluminescence and compound technology, applied in electroluminescence light sources, silicon organic compounds, indium organic compounds, etc., can solve the problems of high driving voltage, unsatisfactory life of OLED devices, and no obvious advantages in power efficiency.

Inactive Publication Date: 2013-07-31
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when existing materials such as BAlq, CBP, etc. are used as hosts for phosphorescent materials, there is no significant advantage in power efficiency (lm / W) compared to OLEDs using fluorescent materials because of higher driving voltages
In addition, the lifetime of OLED devices using such materials is not satisfactory, so there is a need to develop a more stable host material with higher performance

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 example 1

[0078] [Preparation Example 1] Preparation of Compound 1

[0079]

[0080] Preparation of Compound 1-1

[0081] At 100°C, p-2-iodobenzene (30 g, 120.4 mmol), 4-bromophenylboronic acid (26 g, 132.5 mmol), Pd (PPh 3 ) 4 (6.9 g, 6.02 mmol), 150 ml 2M Na 2 CO 3 and 500 ml of toluene for heating. After 4 hours, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), washed with distilled water, washed with anhydrous MgSO 4 Drying, distillation under reduced pressure, and column separation gave compound 1-1 (28 g, 100.68 mmol, 83, 33%).

[0082] Preparation of compound 1-2

[0083] Compound 1-1 (28 g, 100.68 mmol) was mixed with 300 mL of triethyl phosphite, and stirred at 150° C. for 6 hours. The mixture was cooled to room temperature, distilled under reduced pressure, extracted with EA, and washed with distilled water. Subsequently, with anhydrous MgSO 4 Drying, distillation under reduced pressure, and column separation gave compound 1-2 (11 g, 4...

preparation example 2

[0099] [Preparation Example 2] Preparation of Compound 10

[0100]

[0101] Preparation of compound 2-1

[0102] Dibenzo[b,d]thiophen-4-ylboronic acid (10 g, 43.84 mmol), bromonitrobenzene (8.85 g, 43.84 mmol), 70 mL of 2M Na 2 CO 3 The aqueous solution, 200 ml of toluene and 70 ml of ethanol were mixed and stirred under reflux. After 5 hours, the mixture was cooled to room temperature, extracted with EA, washed with distilled water, washed with anhydrous MgSO 4 Dry and distill under reduced pressure. Subsequently, column separation was performed to obtain compound 2-1 (10 g, 32.74 mmol, 74.68%).

[0103] Preparation of Compound 2-2

[0104] Compound 2-1 (10 g, 32.74 mmol) was mixed with 100 mL of triethyl phosphite, and stirred at 150° C. for 7 hours. The mixture was cooled to room temperature, and distilled under reduced pressure. Subsequently, recrystallization was performed using EA to obtain compound 2-2 (7 g, 25.60 mmol, 78.19%).

[0105] Preparation of compou...

preparation example 3

[0112] [Preparation Example 3] Preparation of Compound 19

[0113]

[0114] Preparation of compound 3-1

[0115] 2-(Phenylamino)benzoic acid (50 g, 0.23 mol) was dissolved in 1 L of MeOH, placed in an ice bath, and stirred at 0° C. for 10 minutes. Slowly add SOCl at 0 °C 2 (60 mL, 0.58 mol), and the mixture was stirred at 90° C. under reflux for 12 hours. After the reaction was terminated, the mixture was washed with distilled water and extracted with EA. with anhydrous MgSO 4 The organic layer was dried and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was performed using EA as a developer to obtain compound 3-1 (47 g, 92%).

[0116] Preparation of compound 3-2

[0117] Compound 3-1 (90 g, 0.3 mol) was added to 1.5 L of THF, MeMgBr (3.0 M) (462 mL, 1.38 mol) was added slowly, and the mixture was stirred at room temperature for 12 hours. After the reaction was terminated, the mixture was neutralized with distilled...

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Abstract

Organic electroluminescent compounds comprising a triphenylene conjugated to a five-ring fused heterocyclic system, as depicted in formula 1 are provided. Also provided is an organic electroluminescent device comprising these compounds. The organic electroluminescent compounds disclosed herein exhibit good luminous efficiency and excellent material life. They can be used to manufacture OLED devices very superior in terms of operating life and which consume less power due to improved power efficiency.

Description

technical field [0001] The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. technical background [0002] Among display devices, electroluminescent (EL) devices of self-emissive display devices are preferred because they provide wide viewing angles, excellent contrast, and fast response rates. Eastman Kodak first developed an organic EL device in 1987, which used low-molecular-weight aromatic diamines and aluminum complexes as materials for forming the electroluminescent layer [Appl.Phys.Lett. 51, 913, 1987]. [0003] The most important factor determining the luminous efficiency of an organic light-emitting diode (OLED) is the electroluminescent material. Although fluorescent materials have been widely used as electroluminescent materials so far, from the perspective of electroluminescence mechanism, developing phosphorescent materials is one of the best ways to theoretically increase the lu...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D209/94C07D401/04C07D403/04C07D471/04C07D487/04C07D491/048C07F7/08C09K11/06H01L27/32H01L51/54H05B33/14
CPCY02B20/181C07F15/0033C09K2211/185Y02B20/00H10K85/342H10K85/6572
Inventor 安熙春李琇炫梁绶晋慎孝壬文斗铉金荣佶李孝姃赵英俊权赫柱李暻周金奉玉
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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