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9H-carbazole compounds and electroluminescent devices involving them

A compound, C6-C30 technology, applied in the field of organic electroluminescent devices, can solve the problems of short working life of organic EL devices, no disclosure of carbazole compounds, low glass transition temperature, etc., and achieve improved current characteristics and low driving voltage. , the effect of long working life

Inactive Publication Date: 2014-09-10
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although these phosphorescent host materials provide good luminescence characteristics, they have the following disadvantages: (1) they may degrade during high temperature deposition in vacuum due to their low glass transition temperature and poor thermal stability
Therefore, there is no advantage in terms of power efficiency (lm / W) for EL devices using conventional phosphorescent materials
(3) In addition, the operating life of organic EL devices is short, and there is still a need to improve luminous efficiency
However, it does not disclose a carbazole compound substituted at the 3-position of carbazole with a heterocycloalkyl group or a cycloalkyl group fused to an aromatic ring, and this carbazole compound is directly or indirectly linked to a substituted or unsubstituted Heteroaryl

Method used

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  • 9H-carbazole compounds and electroluminescent devices involving them
  • 9H-carbazole compounds and electroluminescent devices involving them
  • 9H-carbazole compounds and electroluminescent devices involving them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the preparation of compound C-52

[0062]

[0063] Preparation of compound 1-1

[0064] Dibenzo[b,d]thiophen-4-ylboronic acid (14 g, 61 mmol), 3-bromo-9H-carbazole (10 g, 41 mmol) and K 2 CO 3 Pd(PPh 3 ) 4 (2.3 g, 2 mmol). The reaction mixture was stirred at 120°C for 5 hours, cooled to room temperature, and extracted with EA (800 mL). The resulting organic layer was washed with distilled water (200 mL), and distilled under reduced pressure to remove the organic solvent. The resulting solid was washed with methanol, filtered, dried, separated and recrystallized with a silica gel column to obtain compound 1-1 (10 g, 71%).

[0065] Preparation of compound 1-2

[0066] Diphenyl-4-ylboronic acid (50 g, 250 mmol), 1,3-dibromobenzene (46 ml, 380 mmol) and Na 2 CO 3 (66 g, 630 mmol) was dissolved in a mixed solvent of toluene (700 ml) / EtOH (320 ml) / distilled water (320 ml), and Pd(PPh 3 ) 2 Cl 2 (5.6 g, 8 mmol). The reaction mixture was stirr...

Embodiment 2

[0073] Embodiment 2: the preparation of compound C-54

[0074]

[0075] Preparation of compound 2-1

[0076] Carbazole (25 g, 149.5 mmol), 1,3-dibromobenzene (57 mL, 448.5 mmol), CuI (14.2 g, 74.7 mmol), ethylenediamine (5 mL, 74.7 mmol) and K 3 PO 4 (95 g, 448.5 mmol) was dissolved in toluene (450 mL), and the reaction mixture was stirred at reflux at 120° C. for 24 hours. After the reaction was terminated, the reaction mixture was extracted with EA. with anhydrous MgSO 4 The obtained organic layer was dried to remove residual moisture, distilled under reduced pressure to remove the solvent, and filtered through a column to obtain compound 2-1 (42 g, 85%).

[0077] Preparation of compound 2-2

[0078] After compound 2-1 (42 g, 130.3 mmol) was dissolved in THF (500 mL), the reaction mixture was cooled to -78°C. After 10 min, n-BuLi (67 mL, 169.4 mmol, 2.5M in hexane) was added slowly, and the reaction mixture was stirred for 1 h. Then, slowly add B(OMe) 3(23 ...

Embodiment 3

[0083] Embodiment 3: the preparation of compound C-56

[0084]

[0085] Preparation of compound 3-1

[0086] 2,4,6-trichloropyrimidine (10 g, 54.51 mmol), phenylboronic acid (16.6 g, 136.29 mmol), Pd(PPh 3 ) 4 (3.15 g, 2.72 mmol), 2M K 2 CO 3 (50 mL), toluene (100 mL) and ethanol (30 mL) were mixed, and the reaction mixture was stirred at reflux. After 4 hours, the reaction mixture was cooled to room temperature, and distilled water was added. The reaction mixture was extracted with EA. with anhydrous MgSO 4 The obtained organic layer was dried to remove residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to obtain compound 3-1 (7 g, 48%).

[0087] Preparation of compound C-56

[0088] After dissolving NaH (875 mg, 21.8 mmol) in DMF, the solution was stirred. After compound 1-1 (5.1 g, 14.5 mmol) was dissolved in DMF, the solution was added to NaH solution and stirred for 1 hour. After compound 3-1 (4.7 g, 17....

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Abstract

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device containing the same. The compounds according to the present invention have high luminous efficiency and long operation lifetime. Therefore, they can produce an organic electroluminescent device having an improved power consumption.

Description

technical field [0001] The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices using the compounds. Background technique [0002] An electroluminescence (EL) device is a self-luminous device, and its advantages over other types of display devices are that it provides a wider viewing angle, a higher contrast ratio, and has a faster response time. Eastman Kodak first developed an organic EL device by using a small molecule (aromatic diamine) and an aluminum complex as a material for forming a light-emitting layer [Acta Appl. Phys. Lett. 51, 913, 1987]. [0003] The most important factor determining luminous efficiency in an organic EL device is a luminescent material. Hitherto, fluorescent materials have been widely used as light emitting materials. However, based on the mechanism of electroluminescence, developing phosphorescent materials is one of the best ways to theoretically increase the luminous efficiency by ...

Claims

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Application Information

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IPC IPC(8): C07D407/14C07D409/14C07D403/04C07D403/10C07D403/14C07D401/04C07F7/10
CPCC09K11/06C07D401/04C07D403/04C07D403/10C07D403/14C07D407/14C07D409/14C07D487/04C07D491/04C07D495/04C07F7/0812C09K2211/1059C09K2211/1044C09K2211/1088C09K2211/1092H10K85/654H10K85/6572H10K85/657H10K85/40H10K85/636H10K85/649H10K85/633H10K85/615H10K85/631
Inventor 金侈植金希淑李孝姃金慧美文斗铉黄守振李仙优梁绶晋李琇炫李暻周慎孝壬朴景秦赵英俊权赫柱金奉玉
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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