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Benzazole derivative having heteroaryl group and organic light emitting diode device including the same

A technology for benzoxazole and derivatives, applied in the field of benzoxazole derivatives with heteroaryl groups and organic electroluminescent devices containing them, can solve the problems of insufficient organic materials and achieve excellent durability and excellent electron transport ability, the effect of improving luminous efficiency and lifetime characteristics

Active Publication Date: 2020-01-14
LG DISPLAY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of stable and efficient organic materials for organic electroluminescent devices is not enough

Method used

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  • Benzazole derivative having heteroaryl group and organic light emitting diode device including the same
  • Benzazole derivative having heteroaryl group and organic light emitting diode device including the same
  • Benzazole derivative having heteroaryl group and organic light emitting diode device including the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] Intermediate Synthesis Example 1: Intermediate 3 Synthesis

[0132]

[0133] (Synthesis of Intermediate 2)

[0134] 30.0 g (0.16 mol) of 2-amino-4-bromophenol, 16.2 mL (0.16 mol) of benzaldehyde and 200 mL of ethanol were added to a 2L single-necked flask. The mixture was stirred at room temperature for 12 hours. After the reaction was completed, the reaction product was distilled under reduced pressure to remove the solvent from the reaction product to obtain Intermediate 1. Then, Intermediate 1 was dissolved in 800 mL of dichloromethane, followed by slowly adding 36.0 g (0.176 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone at room temperature (DDQ). Then, the mixed solution was stirred at room temperature for 2 hours. After the reaction was completed, the reaction product was purified using short silica gel column chromatography (dichloromethane), and then the purified product was solidified with methanol to obtain 41.0 g of a solid compound (Intermediate ...

Embodiment 3

[0141] Intermediate Synthesis Example 3: Synthesis of Intermediate 5

[0142]

[0143] (Synthesis of intermediate 5)

[0144] 15.0 g (32.4 mmol) of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 12.3 g (48.6 mmol) of bis(pinacolyl)diboron, Pd(dppf)Cl 2 ·CH 2 Cl 2 529 mg (0.647 mmol), 9.53 g (97.1 mmol) of potassium acetate (KOAc), and 323 mL of dioxane were added to a single-necked 500 mL flask to obtain a mixture. Then, the mixture was refluxed and stirred at 90°C for 12 hours. After the reaction was completed, the reaction product was distilled under reduced pressure to remove the solvent from the reaction product. The resulting solid was dissolved in dichloromethane and filtered using celite and washed with dichloromethane. The resulting product was crystallized with methanol to obtain 16.0 g of a solid compound (Intermediate 5) (yield: 96.8%).

[0145] Intermediate Synthesis Example 4: Synthesis of Intermediate 8

[0146]

[0147] (Synthesis of intermedi...

Embodiment 10

[0185] Intermediate Synthesis Example 10: Synthesis of Intermediate 21

[0186]

[0187] (synthesis of intermediate 21)

[0188] Mg0.97g (40.1mmol), I20.184g (0.73mmol) and anhydrous tetrahydrofuran (THF) 10mL were added to a three-necked 250mL flask to obtain a mixture. The mixture was stirred and refluxed for 1 hour. Then, the solution, which was the intermediate 210 g (36.5 mmol), was dissolved in 10 mL of tetrahydrofuran (THF), slowly added dropwise to the mixture, and then refluxed and stirred for 2 hours. Then, the reaction product was cooled to 0°C. Then, the solution, which was the compound 2,4,6-trichloro-1,3,5-triazine (6.7 g, 36.5 mmol) dissolved in 16 mL of tetrahydrofuran (THF), was slowly added dropwise to the cooled reaction product to form a mixed solution. Then, the temperature was slowly raised to room temperature. The mixed solution was then stirred for 12 hours. Then, the reaction product was cooled to 0° C., and distilled water was slowly added dr...

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Abstract

The present invention discloses a benzazole derivative having a heteroaryl group, wherein the benzazole derivative having the heteroaryl group is represented by Chemical Formula 1. Also disclosed is an organic clectroluminescence device including an organic layer containing the benzazole derivative having the heteroaryl group as shown in the description, wherein, each ofZ1, X1, X2, X3, Arl, Ar2, Ar3, ml, m2 and q is the same as defined in the specification.

Description

[0001] Cross References to Related Applications [0002] This application claims priority from Korean Patent Application No. 10-2018-0078289 filed with the Korean Intellectual Property Office on July 5, 2018, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The present disclosure relates to a benzoxazole derivative having a heteroaryl group and an organic electroluminescent device comprising the same. Background technique [0004] An organic electroluminescent device is a self-luminous device that uses organic materials to convert electrical energy into light energy. Generally, in an organic electroluminescent device, a layer of organic material is disposed between an anode and a cathode. [0005] When a voltage is applied between the anode and the cathode, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. Excitons are formed wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04C07D413/10C07D413/14C07D417/04C07D417/10C07D417/14C09K11/06H01L51/50H01L51/54
CPCC07D413/04C07D413/10C07D413/14C07D417/04C07D417/10C07D417/14H10K85/615H10K85/657H10K85/6572H10K50/16H10K50/11H10K50/15H10K50/17H10K50/171H10K50/18H10K85/654C07D263/57C07D277/66H10K85/656H10K50/00C09K2211/1074C09K2211/1081C09K2211/1062C09K2211/1066C09K2211/1077C09K2211/1048C09K2211/1051C09K11/06C09K2211/1033H10K2101/10
Inventor 柳大元金度汉姜慧承韩尙陪文星植金奎植
Owner LG DISPLAY CO LTD
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