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Organic electroluminescent material and application thereof

An electroluminescent device, an organic technology, applied in organic chemistry, circuits, electrical components, etc., can solve the problems of restricting full-color OLED, easy crystallization, small stock displacement, etc., and achieve the effect of high efficiency and high color purity

Inactive Publication Date: 2008-03-19
TSINGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, in the development of OLEDs, red light materials and green light materials have obtained better luminous efficiency and color purity, but the luminous efficiency and color purity of blue light materials have a large gap compared with red light and green light materials. The development of full-color OLED is restricted, so the research of blue light materials has become the focus of current research
[0004] Traditionally, the representative blue light-emitting host structure is condensed-ring aromatic compounds, but the high symmetry of these compounds makes it easy to compile into activated doublets during the evaporation process, making the emission peak red-shifted, resulting in a significant drop in luminous efficiency
The blue-light dye 2,5,8,11-tetra-tert-butylperylene, which was developed earlier, has a hard planar structure, which makes its stock displacement relatively small, and its emission wavelength is relatively blue, but it is easy to crystallize and precipitate, resulting in concentration quenching
Idemitsu's DSA series material 1,4(4-(N,N-diphenylaminophenyl)vinyl)benzene has high luminous efficiency, but due to the small conjugated surface, the luminous range is in the light blue color

Method used

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  • Organic electroluminescent material and application thereof
  • Organic electroluminescent material and application thereof
  • Organic electroluminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment one compound 1:

[0058] Reaction formula:

[0059]

[0060] process:

[0061] Under nitrogen protection, in a 1000ml three-necked flask, dissolve 26.5g of methyl 6-bromo-2-naphthoate in tetrahydrofuran, and cool to below 5°C. Add 14.5g lithium aluminum hydride tetrahydrofuran solution, stir, dropwise add in 15 minutes, and react at 0-5°C for 3 hours. Acidify the reaction solution with dilute hydrochloric acid until the pH value is about 5, filter with suction, separate the liquid to separate the organic layer, extract the aqueous layer with ethyl acetate, combine all the organic layers, wash with water until neutral, dry with anhydrous magnesium sulfate, spin dry, 21.7 g of 6-bromo-2-tetramethanol was obtained. Yield 91.5%

[0062] Under nitrogen protection, 20 g of 6-bromo-2-naphthalenemethanol was dissolved in chloroform to form a white suspension. Dissolve 24g of phosphorus tribromide in chloroform, slowly drop into the reactor, and stir for 2h af...

Embodiment 2

[0067] Example two compound 3:

[0068] Reaction formula:

[0069]

[0070]

[0071] process:

[0072] The implementation process of 6-bromo-2-bromomethylnaphthalene is as described in Example 1

[0073] Put 30g of 6-bromo-2-bromomethylnaphthalene in a 250ml round bottom flask, add 40ml of trimethyl phosphite, and install a condensation drying device. , reflux for 3 hours. After the reaction, the temperature was lowered to 80° C., and the remaining trimethyl phosphite was removed under reduced pressure. A colorless viscous liquid was obtained.

[0074] Add 20 g of benzophenone and sodium hydride to the reaction flask containing the colorless viscous liquid obtained in the previous step, and carefully add 20 ml of chloroform. Heat to reflux and stir, and install a drier on the condenser. Reflux for 3 hours. Pour the product into a 100ml beaker, add 300ml petroleum ether and 300ml water, and separate the liquids. The aqueous phase was extracted with petroleum ether...

Embodiment 3

[0078] Example 3 Compound 4:

[0079]

[0080]

[0081] In a 1000ml three-necked flask equipped with a nitrogen protection device and a magnetic stirrer, 2096-bromo-2-naphthalenemethanol was dissolved in dichloromethane at room temperature, and 40g of pyridinium chlorochromate was added in one go. After reacting for 30 minutes, diethyl ether was added. The product was separated by a column to obtain 18.9 g of 6-bromo-2-naphthaldehyde. Yield 95%

[0082] In the 250ml three-necked flask equipped with magnetic stirrer and nitrogen protection device, put 4.7g6-bromo-2-naphthaldehyde, 4.38g2-naphthaleneboronic acid, 0.136g palladium acetate, 0.32g triphenylphosphine, 5.3g sodium carbonate, pump N 2 5 times. Add 100ml of toluene, then pump N 2 5 times. Heated to reflux for 24h. There is faint blue fluorescence in the solution. The product was separated by a column, the washing liquid was collected, spin-dried, and dried in vacuum at 50°C for 2h. 3.39 g of 6-formyl-2,2...

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Abstract

The invention relates to a new compound and an organic electroluminescent device containing the compound. The structural formula of the compound is shown as below, Ar1 and Ar2 are respectively and independently selected from substituted or unsubstituted aromatic group, aromatic ethylene group, polycyclic aromatic group, polycyclic aromatic ethylene group, aromatic amine group and a polycyclic compound containing nitrogen atoms or a heterocyclic compound containing nitrogen atoms. The invention resolves the problems existing in the colorimetric purity, luminescent efficiency, etc. of the currently used luminescent materials. The material of the invention can be used as a luminescent material, and the electroluminescent device prepared of the material of the invention has the predominant performances of high colorimetric purity, high brightness and high efficiency.

Description

technical field [0001] The invention relates to a novel material and its application in electroluminescent devices, belonging to the technical field of organic electroluminescence display. Background technique [0002] Organic electroluminescence (hereinafter referred to as OLED) and corresponding research began as early as the 1960s. In 1963, p.pope and others first discovered the electroluminescence phenomenon of organic single crystal anthracene, but due to the limitation of technical conditions, its driving voltage was as high as 400V, which failed to attract widespread attention. In 1987, C.W.Tang et al. of Kodak Corporation of the United States used evaporation Alq 3 Made an amorphous film type device with HTM-2, and the driving voltage was reduced to less than 20V, and OLED attracted the attention of the world (US4356429). Due to the advantages of high brightness, wide viewing angle, fast photoelectric response, low voltage, low power consumption, rich colors, high ...

Claims

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Application Information

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IPC IPC(8): C07C211/57C07C15/58C07C251/80C07C245/10C07D209/82C07D413/10C07D215/06C07D213/06C07D471/06C07D219/06C07D251/24H01L51/50H01L51/54
Inventor 邱勇陈瀚李银奎
Owner TSINGHUA UNIV
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