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6H-naphtho[2,1,8,7-klmn]acridine derivative and application thereof

A derivative, acridine technology, applied in the field of new organic materials, can solve the problems of difficult luminescent color, difficult flat panel display, and restricting the development of inorganic EL devices.

Active Publication Date: 2018-02-06
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the production cost of inorganic EL devices is high, the processing is difficult, the efficiency is low, the luminous color is not easy to meet, it is difficult to realize full-color display, and it is difficult to realize large-area flat panel display, which further limits the development of inorganic EL devices.

Method used

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  • 6H-naphtho[2,1,8,7-klmn]acridine derivative and application thereof
  • 6H-naphtho[2,1,8,7-klmn]acridine derivative and application thereof
  • 6H-naphtho[2,1,8,7-klmn]acridine derivative and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Present embodiment prepares formula according to following circuit (M 0 ) intermediate of the structure shown:

[0048]

[0049] This embodiment is synthesized according to the following steps with reference to the method shown in Chinese patent CN103570620A:

[0050] (1) Synthesis of P1

[0051] In a 500ml three-necked flask, add 1-bromo-2-methylnaphthalene, concentrated sulfuric acid, and 1,2-dichloroethane to mix well, control the temperature below 0°C, slowly add nitric acid dropwise while stirring, and keep 0- Stir at 5°C for 2 hours, slowly pour into ice water, separate the layers and wash the organic layer with water, dry and separate by silica gel column chromatography, and elute with ethyl acetate-petroleum ether eluent with a volume ratio of 1:2 , to obtain light yellow product P1;

[0052] (2) Synthesis of P2

[0053] In a 500 ml three-necked flask, add P1, carbon tetrachloride, N-bromosuccinimide and a small amount of benzoyl peroxide prepared in step...

Embodiment 2

[0062] This embodiment prepares the compound shown in formula M1 according to the following synthetic route:

[0063]

[0064] Under nitrogen protection, DMPU (1,3-dimethylpropylene urea) was added to the three-necked flask, and the intermediate M prepared in Example 1 0 , 7-iodo-N,N-p-toluenetriphenylene-2-amine, potassium carbonate, cuprous iodide, and 18-crown-6, mix well, heat the oil bath to reflux for 2 hours, cool down and pour the reaction solution into distilled water , extracted with dichloromethane, dried over magnesium sulfate, concentrated to dryness, and crystallized with a mixed solvent of ethanol and toluene to obtain a yellowish solid M1.

Embodiment 3

[0066] The preparation method of compound M2 in this example is the same as in Example 2, the only difference is that the raw material 7-iodo-N,N-p-toluenetriphenylene-2-amine is replaced by 6,6,9,12,12-penta Methyl-biphenyl-6,12-[1,2-b]N,N-p-tolyltriphenylene-2-amine, other raw materials and preparation methods are the same.

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Abstract

The invention relates to a novel organic material, in particular to a 6H-naphtho[2,1,8,7-klmn]acridine derivative of an organic electroluminescence device and an application of the derivative in the technical field of organic electroluminescence display. The 6H-naphtho[2,1,8,7-klmn]acridine derivative is twisted to a certain extent in the space and the film forming property of the derivative is improved; besides, molecules have large enough conjugated systems, so that the charge migration rate of the material is substantially improved. Device evaluation data fully prove that the compound material has higher hole transfer or hole injection performance and is used for a hole injection or hole transfer material, and the prepared organic electroluminescence device can effectively reduce brightening voltage and improve current efficiency.

Description

technical field [0001] The present invention relates to a novel organic material, in particular to a 6H-naphtho[2,1,8,7-klmn]acridine derivative used in an organic electroluminescence device and its application in the field of organic electroluminescence display technology in the application. Background technique [0002] Electroluminescence (EL) refers to the phenomenon that luminescent materials emit light under the action of an electric field and are excited by current and electric field. It is a luminescence process that directly converts electrical energy into light energy. There are many solid materials that can produce electroluminescence, and those that have been studied more and can reach the level of use are mainly inorganic semiconductor materials. However, the production cost of inorganic EL devices is high, the processing is difficult, the efficiency is low, the luminous color is not easy to meet, it is difficult to realize full-color display, and it is difficu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C07D401/04C07D401/10C07D401/12C07D401/14C07D405/04C07D405/12C07D405/14C07D409/04C07D409/12C07D409/14C07D487/04C07D495/04H01L51/54
CPCC07D221/18C07D401/04C07D401/10C07D401/12C07D401/14C07D405/04C07D405/12C07D405/14C07D409/04C07D409/12C07D409/14C07D487/04C07D495/04H10K85/649H10K85/636H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K85/657
Inventor 范洪涛邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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