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Novel organic electroluminescent compounds and an organic electroluminescent device using the same

A compound and luminescent technology, applied in organic chemistry, electrical solid devices, electrical components, etc., can solve the problems of unrevealed carbazole skeleton, decomposition, inability to provide luminous efficiency, driving voltage and working life, etc.

Active Publication Date: 2014-04-30
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although these phosphorous-containing host materials provide excellent luminescent properties, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may decompose during high-temperature deposition in vacuum
Although an organic EL device containing a phosphorescent material provides higher current efficiency (cd / A) than an organic EL device containing a fluorescent material, a considerably higher driving voltage is required to be applied to the organic EL device, so its power efficiency (lm / W) Difference
(3) In addition, the operating life of organic EL devices is short, and there is still a need to improve luminous efficiency
However, this document does not disclose compounds whose carbazole skeleton contains both dibenzothiophene and nitrogen-containing aryl groups
In addition, organic EL devices containing the compound cannot provide satisfactory luminous efficiency, driving voltage and operating life

Method used

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  • Novel organic electroluminescent compounds and an organic electroluminescent device using the same
  • Novel organic electroluminescent compounds and an organic electroluminescent device using the same
  • Novel organic electroluminescent compounds and an organic electroluminescent device using the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0063] [Preparation Example 1]: Preparation of Compound C-31

[0064]

[0065] Preparation of Compound A-2

[0066] 20g (0.087mol) of compound A-1, 49.6g (0.175mol) of 4-bromoiodobenzene, 3.039g (0.0026mol) of Pd(PPh 3 ) 4 , 1M Na 2 CO 3 and 400mL of toluene were mixed and stirred at reflux. After 3 hours, the mixture was cooled to room temperature, and distilled water was added thereto. The mixture was extracted with EA and MgSO 4 to dry. The resulting solid was distilled under reduced pressure and purified by column chromatography to obtain compound A-2 (23 g, 0.065 mol, 75.6%).

[0067] Preparation of Compound A-3

[0068] 23 g (0.065 mol) of compound A-2 was dissolved in 700 mL of THF. To the mixture was slowly added 39 mL of n-BuLi (0.098 mol, 2.5 M in hexane) at -78 °C. After 1 hour, 30.2 mL (0.131 mol) of triisopropyl borate was added thereto. After stirring at room temperature for 12 hours and adding distilled water to it, the mixture was extracted wit...

preparation Embodiment 2

[0078] [Preparation Example 2]: Preparation of Compound C-41

[0079]

[0080] Preparation of Compound 2-2

[0081] 25g (0.126mol) compound 2-1, 89.3g (0.316mol) 4-bromoiodobenzene, 2.66g (0.0038mol) PdCl 2 (PPh 3 ) 2 , 150mL2M Na 2 CO 3 , 150 mL of toluene and 30 mL of ethanol were mixed, stirred at 110° C. for 3 hours, and then distilled water was added thereto. The mixture was extracted with EA and MgSO 4 Dry and distill under reduced pressure. Purification was performed by column chromatography to obtain 31 g of compound 2-2 (0.100 mol, 80%).

[0082] Preparation of compound 2-3

[0083] 31 g (0.100 mol) of compound 2-2 was dissolved in 750 mL of THF, then 60 mL of n-BuLi (0.150 mol, 2.5M dissolved in hexane) was slowly added at -78°C. After 1 hour, 46 mL (0.200 mol) of triisopropyl borate was added to the mixture. The mixture was stirred at room temperature for 12 hours, and distilled water was added thereto. Then, the mixture was extracted with EA and M...

preparation Embodiment 3

[0089] [Preparation Example 3]: Preparation of Compound C-53

[0090]

[0091] Preparation of Compound C-53

[0092] Compound 3-1, 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (5g, 14.58mmol) and compound A-5 (5.6g, 16.04 mmol) was dissolved in 100 mL DMF, then NaH (0.87 g, 60% in mineral oil, 21.87 mmol) was added thereto. The mixture was stirred at room temperature for 12 hours. After methanol was added, the mixture was filtered under reduced pressure. The obtained solid was purified by column chromatography to obtain compound C-53 (7 g, 10.67 mmol, 73.2%).

[0093] MS / FAB measured value 655.8; calculated value 655.21

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Abstract

An organic electroluminescent compound of formula 1 and an organic electroluminescent device comprising the same is disclosed. The organic electroluminescent compound provides an organic electroluminescent device which has high luminous efficiency and a long operation lifetime and requires a low driving voltage, to thereby have improved power efficiency and 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 greater contrast ratio, and 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 [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, from the perspective of electroluminescence mechanism, phosphorescent materials can theoretically exhibit four (4) times higher luminous efficiency than fluorescent mate...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D407/14H01L51/54C07D403/04C07D409/14C07D403/10H01L27/32
CPCC09K19/12C07D231/26H10K85/111H10K85/649H10K85/631
Inventor 金侈植梁绶晋金希淑朴景泰金承爱李暻周权赫柱金奉玉
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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