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Phenazine group-substituted polycyclic aromatic hydrocarbon derivative and application thereof

A fused-ring aromatic hydrocarbon and phenazine-based technology, which is applied in the field of organic electroluminescence, can solve the problems of reducing OLED costs, disadvantages, and increasing the complexity of device manufacturing processes, etc., to improve luminous efficiency, reduce operating voltage, and good ability to accept electrons Effect

Active Publication Date: 2017-04-05
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The device based on this hybrid electron transport layer improves the device efficiency, but increases the complexity of the device manufacturing process, which is not conducive to reducing the cost of OLED

Method used

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  • Phenazine group-substituted polycyclic aromatic hydrocarbon derivative and application thereof
  • Phenazine group-substituted polycyclic aromatic hydrocarbon derivative and application thereof
  • Phenazine group-substituted polycyclic aromatic hydrocarbon derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The synthesis of embodiment 1 2-bromophenazine

[0065]

[0066] Add 3.91 grams of 4-bromo-o-phenylenediamine (molecular weight 186, 0.021 mol), 2.27 grams of o-benzoquinone (molecular weight 108, 0.021 mol), and ethanol (40 ml) into a 250 ml three-necked flask. 0.2 gram of vitriol oil (concentration is 98%), reacted 4 hours at 65 ℃, after reaction finishes, be cooled to room temperature, filter, wash with ethanol, sherwood oil successively, obtain intermediate compound 2-bromophenazine 5.02 grams (molecular weight 258), yield 92.6%.

Embodiment 2

[0068] Synthesis of compound shown in formula (16)

[0069]

[0070] 1000 ml three-necked flask equipped with magnetic stirring and nitrogen protection, add 5.16 g of 2-bromophenazine (molecular weight 258, 0.02 mol), 11.0 g of 9,10-bis(naphthalene-2-yl)anthracene-2-boronic acid (molecular weight 474 , 0.022mol), tetrakis ((triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M sodium carbonate aqueous solution 80ml, toluene 80ml, ethanol 80ml. After argon replacement, reflux, use thin-layer chromatography ( TLC) method monitoring reaction, after 4.5 hours, TLC finds that raw material bromide reaction is complete, only product point.Lowering temperature, separates organic layer, evaporates to dryness, column chromatography, ethyl acetate / petroleum ether washing, obtains 9.94g formula (12 ), the molecular weight is 608, and the yield is 81.7%.

[0071] Product MS (m / e): 608, elemental analysis (C 46 h 28 N 2 ): theoretical value C: 90.76%, H: 4.64%, N:...

Embodiment 3

[0073] Synthesis of compound shown in formula (17)

[0074] The synthesis procedure is the same as in Example 2, except that 9,10-two (naphthalene-2-yl) anthracene-2-boronic acid is changed to 9-(naphthalene-2-yl)-10-(p-(naphthalene-2-yl ) phenyl) anthracene-2-boronic acid, and other reagents remain unchanged, the compound shown in formula (17) is obtained.

[0075] Product MS (m / e): 684, elemental analysis (C 52 h 32 N 2 ): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; measured value C: 91.23%, H: 4.72%, N: 4.05%.

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Abstract

The invention relates to a phenazine group-substituted polycyclic aromatic hydrocarbon derivative, which has a structure shown in a formula (I). The phenazine group-substituted polycyclic aromatic hydrocarbon derivative is suitable for an electroluminescent display as an ETL material. The usage of the material reduces the turn-on voltage of the electroluminescent display, increases the luminescence efficiency of the device, and increases the usage life of the device.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and specifically relates to a condensed-ring aromatic hydrocarbon derivative substituted by a phenazine group, an intermediate thereof, a preparation method thereof, and an application thereof in electron transport materials. Background technique [0002] The electron transport material traditionally used in electroluminescent devices is Alq 3 , but Alq 3 The electron mobility is relatively low (about 10 -6 cm 2 / Vs). In order to improve the electron transport performance of electroluminescent devices, researchers have done a lot of exploratory research work. [0003] LG Chem reported a series of pyrene derivatives in the patent specification CN 101003508A in China, which are used as electron transport and injection materials in electroluminescent devices to improve the luminous efficiency of the devices. Cao Yong and others synthesized FFF-Blm4 (J.Am.Chem.Soc.; (Communication); 20...

Claims

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Application Information

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IPC IPC(8): C07D241/46H01L51/54
CPCC07D241/46H10K85/6572
Inventor 范洪涛李银奎邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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