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Organic compound, and electron transport material and applications thereof

An organic compound, selected technology, applied in the field of organic compounds and electron transport materials, can solve problems such as low electron mobility, unbalanced electron transport and hole transport, and failure to meet the performance requirements of electroluminescent devices, and achieve the purpose of inhibiting molecular The increase of the gravitational force, the improvement of luminous efficiency and working life, and the effect of improving the drift voltage rise

Pending Publication Date: 2020-04-14
XIAMEN TIANMA MICRO ELECTRONICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Alq 3 The electron mobility is relatively low, about l0 -6 cm 2 / Vs, which makes the electron transport and hole transport of the device unbalanced. With the development of OLED devices towards commercialization and practicality, Alq 3 It has been unable to meet the performance requirements of electroluminescent devices

Method used

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  • Organic compound, and electron transport material and applications thereof
  • Organic compound, and electron transport material and applications thereof
  • Organic compound, and electron transport material and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] This embodiment provides an organic compound with the following structure:

[0132]

[0133] The preparation method of the organic compound M16 comprises the following steps:

[0134] (1)

[0135] In a 100mL three-neck flask, first dissolve S1 (10mmol, wherein TMS is trimethylsilyl) in 20mL of concentrated sulfuric acid, and use an ice-water bath to control the temperature; after stirring evenly at a certain speed, add concentrated nitric acid to the reaction system (15mmol) to react for 2h; under ice-water bath, adjust the reaction solution to neutral with NaOH aqueous solution; after the reaction, extract with ether, dry the obtained organic phase with anhydrous sodium sulfate, distill off the solvent, and use column Purified by analytical method to obtain intermediate S2 (9.5 mmol, yield 95%).

[0136] Test the structure of intermediate S2: MALDI-TOFMS (m / z) obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: C 12 h 13 C...

Embodiment 2

[0158] This embodiment provides an organic compound with the following structure:

[0159]

[0160] The preparation method of the organic compound M19 comprises the following steps:

[0161] Obtain intermediate S10 according to the method of steps (1) to (6) in Example 1;

[0162] (7)

[0163] Intermediate S10 (1mmol) and tetramethylethylenediamine (2.5mmol) were added to 90mL THF, the temperature was lowered to -78°C in an ethanol bath, and tert-butyllithium (t-BuLi, 2.5mmol) was added within 15min Dropwise into the reaction system, stirred at low temperature for 1h. Add S12 (2.5 mmol) at low temperature, stir at low temperature for 1 h, then return to room temperature naturally, and stir overnight. After the reaction, extract with water and ethyl acetate, the organic phase was washed with anhydrous Na 2 SO 4 dry. The crude product was purified by silica gel column chromatography, using a mixed solvent of n-hexane and chloroform at a volume ratio of 5:1 as the elue...

Embodiment 3

[0168] This embodiment provides an organic compound with the following structure:

[0169]

[0170] The preparation method of the organic compound M2 comprises the following steps:

[0171] Obtain intermediate S10 according to the method of steps (1) to (6) in Example 1;

[0172] (7)

[0173] Dissolve intermediates S10 (2mmol) and S13 (1mmol) in 30mL toluene under nitrogen protection, add Pd(PPh 3 ) 4 (0.1mmol) as a catalyst, add 4mL potassium carbonate aqueous solution (2mol / L), and reflux for 12h. After the reaction, it was extracted three times with saturated brine and ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. All the solvent was distilled off under reduced pressure, and the crude product was collected. The crude product was purified by silica gel column chromatography, using a mixed solvent of n-hexane and chloroform at a volume ratio of 5:2 as the eluent, and finally purified to obtain the solid target product M...

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Abstract

The invention provides an organic compound, and an electron transport material and applications thereof, wherein the organic compound has a structure represented by a formula I. According to the invention, through the special design of a molecular structure and a substituent group, tridentate coordination or tetradentate coordination can be generated between the organic compound and a metal, so that the organic compound can be stably and firmly combined with the metal, the organic compound has high stability and long service life when being used as an electron transmission material, and the problem of drift voltage rise is effectively improved; the organic compound has large rigid distortion, so that the increase of intermolecular attraction can be inhibited, and the excessive intermolecular attraction caused by formation of a planar structure can be avoided; and the organic compound used as an electron transport material can be applied to an electron transport layer and / or an electroninjection layer of an OLED device, so that the luminous efficiency of the device can be effectively improved, the service life of the device can be effectively prolonged, and the turn-on voltage canbe reduced.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound, an electron transport material and applications thereof. Background technique [0002] Organic electroluminescent technology is an emerging technology in the field of optoelectronics. Compared with traditional inorganic electroluminescent devices, organic electroluminescent devices (Organic LightEmitting Diode, OLED) have self-illumination, wide viewing angle, ultra-thin, fast response, and luminescence. With the advantages of high efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption, it has been widely used in industries such as flat panel display, flexible display, solid-state lighting, and vehicle display. At present, OLED has entered the stage of industrialization, and the growing display demand has driven the rapid development of OLED devices and org...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C09K11/06H01L51/54H01L51/50
CPCC07F7/0812C07F7/0814C09K11/06C09K2211/1044C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/6576H10K85/6574H10K85/40H10K85/6572H10K50/16H10K50/171H10K85/654H10K50/166
Inventor 牛晶华戴铭志高威李侠
Owner XIAMEN TIANMA MICRO ELECTRONICS
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