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An organic electroluminescent compound and an organic electroluminescent device comprising the same

A technology of luminescence and compounds, which is applied in the field of organic electroluminescent compounds, can solve the problems of reduced device life, non-disclosure of fluorene, poor thermal stability, etc., and achieve excellent current and power efficiency and long life.

Active Publication Date: 2016-05-11
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 light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade in vacuum during high-temperature deposition processes, and the lifetime of the device is reduced
(3) In addition, the lifetime of the organic EL device is short, and there is still a need to improve the luminous efficiency
However, the above references do not disclose compounds in which the 9-position of fluorene is substituted by diarylamine or heteroarylamine, and fluorene, dibenzothiophene or dibenzofuran

Method used

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  • An organic electroluminescent compound and an organic electroluminescent device comprising the same
  • An organic electroluminescent compound and an organic electroluminescent device comprising the same
  • An organic electroluminescent compound and an organic electroluminescent device comprising the same

Examples

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Effect test

example 1

[0107] Example 1: Preparation of Compound C-6

[0108]

[0109] Preparation of compound 1-1

[0110] After introducing dibenzofuran (30 g, 178 mmol) and 500 mL of tetrahydrofuran into the reaction vessel, the vessel was cooled to -78°C under nitrogen atmosphere. Then 71 mL of n-butyllithium (2.5M, 178 mmol) was slowly added dropwise to the mixture. After stirring the mixture at -78°C for 30 minutes, it was stirred at room temperature for 3 hours and cooled to -78°C. Thereafter, fluorenone (32 g, 178 mmol) dissolved in 500 mL of tetrahydrofuran was slowly added dropwise to the mixture. After the addition, the reaction temperature was allowed to warm slowly to room temperature, and the mixture was stirred for 16 hours. Aqueous ammonium chloride solution was then added to the reaction solution to complete the reaction, and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried using magnesium sulfate, and the solvent was remov...

example 2

[0118] Example 2: Preparation of Compound C-8

[0119]

[0120] Preparation of compound 2-2

[0121] After compound 2-1 (30 g, 86.1 mmol), 4-bromotriphenylamine (84 g, 259 mmol) and 600 mL of dichloromethane (MC) were introduced into the reaction vessel, the vessel was introduced into a nitrogen atmosphere. Thereafter, 3 mL of Eaton's reagent was slowly added dropwise to the mixture. After the mixture was stirred at room temperature for 2 hours, ethanol and distilled water were added thereto to complete the reaction, and the mixture was extracted with dichloromethane. The extracted organic layer was then dried using magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining material was then purified by column chromatography to obtain compound 2-2 (42 g, 74%).

[0122] Preparation of Compound C-8

[0123] Compound 2-2 (10g, 26.9mmol), 2-naphthylboronic acid (3.2g, 18.4mmol), tetrakis (triphenylphosphine) palladium (0.7g, 1.08mmol), pot...

example 3

[0125] Example 3: Preparation of Compound C-38

[0126]

[0127] Preparation of compound 3-1

[0128] After introducing 2-bromodibenzothiophene (27 g, 103 mmol) and 340 mL of tetrahydrofuran into the reaction vessel, the vessel was cooled to -78°C under nitrogen atmosphere. Then 33 mL of n-butyllithium (2.5M, 82 mmol) was slowly added dropwise to the mixture. After stirring the mixture at -78°C for 2 hours, 9H-fluoren-9-one (19 g, 103 mmol) dissolved in 340 mL of tetrahydrofuran was slowly added dropwise to the mixture. After the addition, the reaction temperature was allowed to warm slowly to room temperature, and the mixture was stirred for 30 minutes. Aqueous ammonium chloride solution was then added to the reaction solution to complete the reaction, and the mixture was extracted with ethyl acetate. The extracted organic layer was then dried using magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining material was then purified by...

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Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present invention has excellent thermal stability due to a high glass transition temperature. By using the organic electroluminescent compound according to the present invention, it is possible to produce an organic electroluminescent device having excellent current / power efficiency and long lifespan.

Description

technical field [0001] The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the compound. Background technique [0002] Electroluminescent devices (EL devices) are self-luminescent devices that are advantageous in that they provide a wider viewing angle, greater contrast ratio, and faster response time. The organic EL device was originally developed by Eastman Kodak by using small aromatic diamine molecules and aluminum complexes as materials for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987]. [0003] The most important factor determining the luminous efficiency in an organic EL device is the luminescent material. Fluorescent materials have been widely used as light-emitting materials so far. However, in view of the mechanism of electroluminescence, since phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared with fluorescent materials, the deve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D307/91C07D333/76C07C211/54C07C211/61C07D209/88C07D405/12C07D409/12H01L27/32H01L51/54
CPCC07D333/76C07C211/54C07C211/61C07D405/12C07D409/12C07D209/88C07D307/91C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1088C09K2211/1092C07C2603/18H10K85/633H10K85/615H10K85/631H10K85/6576H10K85/6574H10K50/11H10K2101/10H10K50/15H10K85/649
Inventor J-S·俊D-H·文H-C·安T-J·李C-S·金Y-J·曹K-J·李
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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