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Novel compounds for organic electronic material and organic electronic device using the same

A technology of organic electronic materials and compounds, applied in the fields of organic chemistry, compounds of group 4/14 elements of the periodic table, compounds of group 5/15 elements of the periodic table, etc., can solve problems such as unsatisfactory luminous efficiency

Inactive Publication Date: 2014-06-18
GRACEL DISPLAY INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, satisfactory properties are not obtained in durability of organic EL devices or luminous efficiency derived from hole injection / transport properties

Method used

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  • Novel compounds for organic electronic material and organic electronic device using the same
  • Novel compounds for organic electronic material and organic electronic device using the same
  • Novel compounds for organic electronic material and organic electronic device using the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0249] Preparation of Example 1 Compound (1)

[0250]

[0251] Preparation of compound (A)

[0252] Carbazole (20g, 119.6mmmol), methyl 2-iodobenzoate (26.4mL, 179.4mmol), K 2 CO 3 (21.5g, 155.5mmol), Cu (1.52g, 23.9mmol) and CuI (1.14g, 5.98mmol) were dissolved in dibutyl ether (500mL), and the solution was stirred at reflux for 48 hours under an argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with water (800 mL). The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography with hexane and ethyl acetate (4:1), and recrystallized from ethanol (300 mL) to obtain compound (A) (24.5 g, 68%).

[0253] Preparation of compound (B)

[0254] Compound (A) (15.0 g, 49.8 mmol) was dissolved in diethyl ether (100 mL), and the solution was frozen to -78°C. Methyl lithium (1.6M in diethyl ether, 78 mL, 124.4 mmol) was added thereto, and the mixture was stirred for 1 h...

preparation Embodiment 2

[0261] Preparation of Preparation Example 2 Compound (320)

[0262]

[0263] Preparation of compound (E)

[0264] Compound (C) (7 g, 24.7 mmol) was dissolved in dichloromethane (100 mL), and N-bromosuccinimide (10.5 g, 59.2 mmol) was added thereto at 0°C. Maintaining this temperature, the solution was stirred for 5 hours. Distilled water (150 mL) was added to terminate the reaction, the mixture was extracted with dichloromethane (100 mL), and the extract was evaporated under reduced pressure. Compound (E) (7.4 g, 68%) was obtained by recrystallization from ethanol / acetone (1:2 v / v).

[0265] Preparation of compound (320)

[0266] Compound (E) (5g, 13.8mmol), phenylboronic acid (3.8g, 30.36mmol) and Pd(PPh 3 ) 4 (1.6 g, 1.04 mmol) was dissolved in toluene (100 mL) and ethanol (50 mL), and 2M aqueous sodium carbonate solution (50 mL) was added thereto. After stirring under reflux at 120°C for 4 hours, the reaction mixture was cooled to 25°C, and distilled water (200 mL)...

preparation Embodiment 3

[0267] Preparation of Preparation Example 3 Compound (462)

[0268]

[0269] Preparation of compound (F)

[0270] Carbazole (20g, 119.6mmmol), methyl 5-bromo-2-iodobenzoate (26.4mL, 179.4mmol), K 2 CO 3 (21.5g, 155.5mmol), Cu (1.52g, 23.9mmol) and CuI (1.14g, 5.98mmol) were dissolved in dibutyl ether (500mL), and the solution was stirred at reflux for 48 hours under an argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with water (800 mL). The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography with hexane and ethyl acetate (4:1), and recrystallized from ethanol (300 mL) to obtain compound (F) (24.5 g, 58%).

[0271] Preparation of compound (G)

[0272] Compound (F) (15.0 g, 49.8 mmol) was dissolved in diethyl ether (100 mL), and the solution was frozen to -78°C. Methyl lithium (1.6M in diethyl ether, 78 mL, 124.4 mmol) was added thereto, and the compo...

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Abstract

Provided are novel compounds for organic electronic material, and organic electronic devices comprising the same. Specifically, the compounds for organic electronic material according to the invention are characterized in that they are represented by Chemical Formula (1) or (2): wherein, R 1 , R 2 and R 3 cannot be hydrogen all at the same time; excluding the case wherein or independently represents diphenylamino group.

Description

[0001] The patent application for this invention is the international application number PCT / KR2009 / 006350, the international application date is October 30, 2009, the application number entering the Chinese national phase is 200980143114.9, and the name is "New compounds for organic electronic materials and the use of the A divisional application of the invention patent application for "organic electronic devices of compounds". technical field [0002] The present invention relates to novel compounds for use in organic electronic materials and organic electronic devices using such compounds. More particularly, the present invention relates to novel compounds for organic electronic materials with high efficiency, and organic electronic devices comprising the compounds as phosphor hosts in hole transport layers or hole injection layers or electroluminescent layers. Background technique [0003] Among display devices, an electroluminescence device (EL device) is a self-luminou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16C07F7/10C07F9/6568C09K11/06H01L51/54H01L51/46
CPCC09K2211/185C09K2211/1033C09K2211/1092C09K2211/1044H01L51/0061C09K2211/1088H01L51/0072C09K2211/1007H01L51/5012C09K2211/1029C09K2211/1011Y02E10/549C09K11/06C07D471/06C07D471/16C07F7/0812C07F7/0816C07F9/65683H10K85/624H10K85/636H10K85/626H10K85/633H10K85/631H10K85/654H10K85/6574H10K85/6572H10K85/657H10K85/40H10K50/11C07D241/36C07D498/04C07D497/04
Inventor 阴盛镇赵英俊权赫柱金奉玉金圣珉尹胜洙
Owner GRACEL DISPLAY INC
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