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Novel organic electroluminescent compounds and organic electroluminescent device using the same

A compound and luminescent technology, which is applied in the direction of electroluminescent light sources, silicon organic compounds, indium organic compounds, etc., can solve the problems of short working life, low glass transition temperature, and poor thermal stability of organic EL devices, and achieve improved current properties, good life properties, and the effects of good layering properties

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 materials provide good luminescent properties, they have some disadvantages as follows: (1) Because of their low glass transition temperature and poor thermal stability, they may degrade during high-temperature deposition in vacuum
However, it has a higher drive voltage, so it has less advantage in power efficiency (lm / W)
(3) In addition, the working life of organic EL devices is short, and its luminous efficiency still needs to be improved
However, this document does not disclose compounds formed by attaching a heteroaryl to a benzo[9,10]phenanthrenyl, wherein the heteroaryl is carbazole fused to a ring such as benzothiophene, indole , indene, benzofuran or silole, etc.

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Embodiment 1: the preparation of compound C-28

[0092]

[0093] Preparation of compound 1-1

[0094] 1,4-Dibromo-2-nitrobenzene (30g, 131mmol), dibenzo[b,d]thiophen-4-ylboronic acid (44g, 156.6mmol), Pd(PPh 3 ) 4 (7.6g, 6.58mmol) and Na 2 CO 3 (41.8 g, 394 mmol) was added to a mixture of toluene (500 mL), ethanol (100 mL) and purified water (100 mL), and the mixture was stirred at 120° C. for 3 hours. After the reaction was complete, the mixture was allowed to stand and the aqueous layer was removed. The obtained organic layer was concentrated, followed by purification through a silica column to obtain Compound 1-1 (40 g, 80%).

[0095] Preparation of compound 1-2

[0096] After the mixture 1-1 (40 g, 104 mmol) was dissolved in 1,2-dichlorobenzene (150 mL), triethoxyphosphine (150 mL) was added. The reaction mixture was stirred at 150°C for 20 hours. The reaction mixture was cooled to room temperature, followed by distillation under reduced pressure to ...

Embodiment 2

[0110] Embodiment 2: the preparation of compound C-47

[0111]

[0112] Preparation of compound 2-1

[0113] 2-Bromo-9,9-dimethyl-9H-fluorene (50.0 g, 183 mmol), 2-chloroaniline (28.4 mL, 274.5 mmol), Pd(OAc) 2 (1.64g, 7.32mmol), P(t-Bu) 3After (50%) (7.2 mL, 14.64 mmol) and NaOt-Bu (43.97 g, 457.5 mmol) were added to toluene (450 mL), the reaction mixture was stirred at reflux for 1 day. After the reaction was completed, the mixture was cooled to room temperature, followed by extraction with distilled water and ethyl acetate. The organic layer was distilled under reduced pressure, and then filtered through a column with dichloromethane (MC) and hexane to obtain compound 2-1 (46.7 g, 80%).

[0114] Preparation of compound 2-2

[0115] Compound 2-1 (46.7g, 14.6 mmol), Pd(OAc) 2 (1.64g, 7.3 mmol), di-tert-butyl (methyl) phosphine HBF 4 (di-t-butyl(methyl)phosphine·HBF 4 ) (3.62g, 14.6mmol), K 2 CO 3 (60.5 g, 438 mmol) and dimethylamide (DMA) (50 mL) were mixed,...

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Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device containing the same. Using the organic electroluminescent compounds of the present invention, it is possible to manufacture an OLED device with a long operating lifespan and high luminous efficiency. In addition, the compounds can improve the power efficiency of the device to reduce overall 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 [Appl. Phys. Lett. 51, 913, 1987] by using aromatic diamine small molecules and aluminum complexes as materials for forming a light-emitting layer. [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, from the viewpoint of electroluminescent mechanism, since phosphorescent materials can theoretically increase luminous efficiency by 4 times compared with fluorescent mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/54C07D209/58C07D491/02C07D495/02C07F7/02C07D409/04
CPCC07F7/0812C07D491/02H05B33/14C09K2211/1092C07D495/02C09K2211/1044C07D209/58H01L51/0085C09K2211/1088H01L51/0072C07D409/04C09K2211/1007H01L2251/308H01L51/0071H01L51/5016C09K11/06H01L51/0054C09K2211/1059C09K2211/1029C09K2211/1011H10K85/622H10K85/657H10K85/6572H10K85/342H10K50/11H10K2101/10H10K2102/103C07F15/0033
Inventor 尹石根李琇炫朴景秦金承爱权赫柱李暻周金奉玉
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC