6-mesitylene-6h-6-boron hetero benzo[cd]pyrene derivative containing substituted or non-substituted carbazolyl, and preparation method and application thereof, and luminescent device comprising same

A technology of -6H-6-, trimethylol, applied in the field of 6-mesityl-6H-6-borabenzo[cd]pyrene derivatives, can solve the problems of low transmission efficiency and the like

Active Publication Date: 2013-07-03
KUNSHAN VISIONOX DISPLAY TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] For this reason, the technical problem to be solved by the present invention lies in the shortcomings of the low transmission efficiency of organic light-emitting host materials applied to phosphorescence in the prior art, thereby providing a 6-

Method used

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  • 6-mesitylene-6h-6-boron hetero benzo[cd]pyrene derivative containing substituted or non-substituted carbazolyl, and preparation method and application thereof, and luminescent device comprising same
  • 6-mesitylene-6h-6-boron hetero benzo[cd]pyrene derivative containing substituted or non-substituted carbazolyl, and preparation method and application thereof, and luminescent device comprising same
  • 6-mesitylene-6h-6-boron hetero benzo[cd]pyrene derivative containing substituted or non-substituted carbazolyl, and preparation method and application thereof, and luminescent device comprising same

Examples

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preparation example Construction

[0088] Preparation examples of derivatives in the present invention

[0089] The preparation example of intermediate

[0090] (1) Preparation of carbazole derivatives

[0091] The synthesis of carbazole derivatives involved in the present invention is carried out by Cagogan reaction (j.Chem.Soc., 1965, 4831), that is, the co-heating of the adjacent aryl nitro functional group and trialkyl phosphite, the nitro group is reduced to Nitrogen, and then attack the ortho aromatic ring of the molecule to generate carbazole derivatives.

[0092] The general steps of its synthesis are as follows:

[0093]

[0094] Under the protection of inert gas, take 0.1mol o-nitroaromatic compound and 0.2-08mol triethyl phosphite, put them in a round bottom flask, reflux under magnetic stirring for 10-24h, and then distill off excess triethyl phosphite under reduced pressure , cooled to room temperature and filtered, the solid was subjected to H 2 O, ethanol, and petroleum ether were washed s...

Embodiment 1

[0107]

[0108] This example is the synthetic procedure of derivative (1): under the protection of nitrogen, add 25.7g (0.05mol) 2,10-dibromo-6-mesityl-6H-6-boron to a 250mL three-necked round-bottomed flask Heterobenzo[cd]pyrene, 20.1g (0.12mol) carbazole, 0.2g (2mol%) CuI, 20.7g (0.15mol) K 2 CO 3 , 0.8 g (6 mol%) 18-crown-6, 5 mL 1,3-dimethylpropylene urea (DMPU) and 50 mL o-dichlorobenzene. Reflux reaction under magnetic stirring for 12h, then cool, add 200mL CH 2 Cl 2 , washed 2-3 times with an appropriate amount of water, separated, and the organic phase was washed with anhydrous MgSO 4 After drying, the organic solvent was removed by rotary evaporation to obtain the crude product. After separation by silica gel column chromatography, 22.8 g of white crystals were obtained, with a yield of 66.6%. In this step the Ullmann condensation reaction takes place.

[0109] Derivative (1) product MS (m / z): 686; elemental analysis (C 51 h 35 BN 2 ): theoretical value C:...

Embodiment 2

[0111] The present embodiment is the synthetic steps of derivative (2):

[0112] (1) Synthesis of 2-phenyl-9H-carbazole

[0113]

[0114] Under nitrogen protection, 28.1g (0.1mol) 1,4-dibromo-2-nitrobenzene, 29.2g (0.24mol) phenylboronic acid, 2.31g (2mol%) Pd(PPh 3 ) 4 and 100mL of toluene and 100mL of ethanol mixture, add 75mL concentration of 2mol L -1 sodium carbonate solution, stirred and reacted in an oil bath at 100°C for 3h, cooled, separated the organic phase, washed the organic phase with water 2-3 times and washed with anhydrous MgSO 4 After drying, the organic solvent was removed by rotary evaporation to obtain the crude product. Recrystallized from absolute ethanol to obtain 22.6 g of Intermediate A. Yield 82.5%.

[0115] Under nitrogen protection, take 22.0g (0.08) mol of intermediate A, 66.4g (0.4mol) of triethyl phosphite, place in a 250mL three-neck round-bottomed flask, reflux under magnetic stirring for 12 hours, and then distill off excess phosphite...

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Abstract

The invention provides a 6-mesitylene-6H-6-boron hetero benzo[cd]pyrene derivative containing substituted or non-substituted carbazolyl. Due to the bipolar transmission characteristic, the derivative can effectively balance transmission of carriers and improve transmission efficiency, by using the derivative in phosphorescent organic light-emitting devices as a main material. The invention also provides an organic electroluminescent device that has increased current efficiency, reduced turn-on voltage and good stability, and solves the problems of low transmission efficiency or poor stability of phosphorescent organic light-emitting main materials in the prior art.

Description

technical field [0001] The invention relates to a 6-mesityl-6H-6-borabenzo[cd]pyrene derivative containing a substituted or unsubstituted carbazolyl group, and its application in the field of organic electroluminescence lighting and display technology application. Particularly, the 6-mesityl-6H-6-borabenzo[cd]pyrene derivative containing substituted or unsubstituted carbazolyl of the present invention can be used in the organic functional layer of an organic electroluminescent device. The phosphorescent host material enables organic electronic light-emitting devices to achieve improved brightness and luminous efficiency under low driving voltage. Background technique [0002] In 1998, Professor Ma Yuguang of Jilin University doped poly-N-vinylcarbazole (PVK) with an osmium complex [Os(CN) 2 (PPh 3 ) 2 bpy] prepared an electrophosphorescent device (Synthetic Metals, 1998, 94: 245-248). In the same year, Thomson and Forrest cooperated to dope the phosphorescent material p...

Claims

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Application Information

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IPC IPC(8): C07F5/02H01L51/54
Inventor 邱勇刘飞李银奎
Owner KUNSHAN VISIONOX DISPLAY TECH
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