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Novel organic electroluminescence compounds and organic electroluminescence device using the same

A compound and unsubstituted technology, applied in the field of organic electroluminescent devices, can solve the problems of no disclosure of carbazole compounds, low glass transition temperature, poor thermal stability, etc., and achieve improved current characteristics, low driving voltage, good layering sexual effect

Inactive Publication Date: 2014-05-28
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 materials provide good luminescence characteristics, they have the disadvantage that they may degrade during high temperature deposition in vacuum due to their low glass transition temperature and poor thermal stability
However, it does not disclose a carbazole compound fused at the nitrogen position, which is directly or indirectly attached to a heteroaryl substituted with a carbazolyl

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: the preparation of compound C-40

[0073]

[0074] Preparation of Compound 1-1

[0075] 2-Bromo-9,9-dimethyl-9H-fluorene (50 g, 183.0 mmol), 2-chloroaniline (38 mL, 366.1 mmol), Pd(OAc) 2 (1.2 g, 5.5 mmol), P(t-Bu) 3 (8.8 mL, 18.3 mmol), NaOt-Bu (35 g, 366.1 mmol) and toluene (180 mL) were mixed, and the reaction mixture was stirred at reflux for 2.5 hours. After terminating the reaction, the reaction mixture was filtered, and the filter cake was washed with dichloromethane. The resulting organic layer was washed with pure water and washed with MgSO 4 Dry and concentrate under reduced pressure. Then, the crude oil was filtered through silica gel, and the remaining solution was concentrated under reduced pressure to obtain Compound 1-1 (47 g, 80%).

[0076] Preparation of compound 1-2

[0077] Compound 1-1 (46 g, 143.8 mmol), Pd(OAc) 2 (968 mg, 4.3 mmol), di-tert-butyl(methyl)phosphorus tetrafluoroborate (2 g, 4.31 mmol) and DMAc (200 mL) wer...

Embodiment 2

[0083] Embodiment 2: the preparation of compound C-94

[0084]

[0085] Preparation of compound 2-1

[0086] 1-Bromo-2-nitrobenzene (85 g, 0.42 mol), dibenzo[b,d]thiophen-2-ylboronic acid (80 g, 0.35 mol), Pd(PPh 3 ) 4 (20g, 0.018mol), K 2 CO 3 (116 g, 1.0 mol), toluene (1700 mL), EtOH (440 mL), and distilled water (440 mL) were mixed, and the reaction mixture was stirred at 120° C. for 12 hours. After the reaction was terminated, the reaction mixture was extracted with EA. with MgSO 4 The resulting organic layer was dried, filtered, evaporated under reduced pressure to remove the solvent, and filtered through a column to obtain compound 2-1 (93 g, 87%).

[0087] Preparation of Compound 2-2

[0088] Compound 2-1 (88 g, 0.29 mol), P(OEt) 3 (960 mL, 0.4M) and triethyl phosphite (960 mL) were mixed, and the reaction mixture was stirred at 90° C. for 12 hours. After terminating the reaction, the reaction mixture was distilled to remove triethyl phosphite, and fil...

Embodiment 3

[0092] Embodiment 3: the preparation of compound C-105

[0093]

[0094] Preparation of compound 3-1

[0095] Carbazole (26 g, 155.49 mmol), 4-bromoiodobenzene (87 g, 310.9 mmol), CuI (14.8 g, 77.74 mmol), ethylenediamine (9.3 g, 155.49 mmol), K 3 PO 4 (99 g, 499.47 mmol) and toluene (1000 ml) were mixed, and the reaction mixture was stirred at reflux. After 15 h, the reaction mixture was cooled to room temperature and filtered under reduced pressure to remove CuI and K 3 PO 4 . The remaining solution was extracted with MC, washed with distilled water, and then filtered through a column to obtain Compound 3-1 (35 g, 70%).

[0096] Preparation of Compound 3-2

[0097] After compound 3-1 (35 g, 108.6 mmol) was dissolved in THF (600 mL), n-BuLi (52 mL, 130.35 mmol, 2.5 M in hexane) was added to the reaction mixture at -78 °C , and the reaction mixture was stirred for 1 h. The reaction mixture was stirred at room temperature for 12 hours and B(Oi-Pr) was slowly ad...

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Abstract

The present invention relates to a novel organic luminescent compound and an organic electroluminescence 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 which improves 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, higher contrast ratio and 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 [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 4 times. Irid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D495/04C07D491/04C07D403/04C07D409/14C07F7/02C09K11/06H01L51/54H01L27/32H05B33/14
CPCC07D403/14C07D409/14C07D487/04C07D491/048C07D495/04C07F7/0814C09K11/06C09K2211/1059C09K2211/1044C09K2211/1029C09K2211/1092C09K2211/1088H10K85/615H10K85/654H10K85/657H10K85/6576H10K85/40H10K85/6572C09K2211/1007C07B59/002C07D403/04C07D491/04C07F7/0812C09B57/00C09B57/10H10K85/6574H10K50/11H10K50/19
Inventor 梁绶晋黄守振李仙优金侈植李孝姃朴景秦赵英俊
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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