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Triphenyl-based organic compound, organic electroluminescent material and device

An organic compound, triphenylene technology, applied in luminescent materials, organic chemistry, electro-solid devices, etc., can solve the problems of short service life, low luminous efficiency, high starting voltage, and achieve improved efficiency, high electron mobility, reduced Effect of driving voltage

Active Publication Date: 2021-05-28
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The selection and use of organic electroluminescent materials for each layer plays a decisive role in the performance of OLED devices. At present, OLED devices still have many defects such as high starting voltage, low luminous efficiency, and short service life. Looking for organic electroluminescent materials with better performance Luminescent materials have become the top priority at present. The rational use of organic electroluminescent materials can greatly improve the performance of OLED devices and improve the application prospects.

Method used

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  • Triphenyl-based organic compound, organic electroluminescent material and device
  • Triphenyl-based organic compound, organic electroluminescent material and device
  • Triphenyl-based organic compound, organic electroluminescent material and device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]

[0045] The synthetic method of organic compound (1) is as follows:

[0046] S1:

[0047]

[0048] Compound 1-a (5g, 317.76g / mol, 15.89mmol), compound 1-b (1.1eq, 2.57g, 146.94g / mol, 17.47mmol) and sodium carbonate (2eq, 3.37g, 105.99g / mol, 31.77mmol) was added to ethylene glycol diamine ether (100g, 20 times the quality of compound 1-a) and water (100g, 20 times the quality of compound 1-a), stirred and mixed and then added three (o-toluene Base) phosphine (5%eq, 0.24g, 304.37g / mol, 0.79mmol) and palladium (II) acetate (1%eq, 0.04g, 224.51g / mol, 0.16mmol), after warming up to reflux for 15h, the The organic phase was separated, washed with water, and concentrated under reduced pressure to obtain a crude product, which was subjected to column chromatography to obtain compound 1-c (4.96 g, yield 91.8%), MS (EI): 339 (M+).

[0049] S2:

[0050]

[0051] Compound 1-c (4g, 339.97g / mol, 11.84mmol), compound 1-d (1.1eq, 4.53g,

[0052] 348.20g / mol, 13.02mmol) an...

Embodiment 2

[0057]

[0058] The synthetic method of organic compound (6) is as follows:

[0059]

[0060] Compound 2-a (4g, 563.45g / mol, 7.12mmol), compound 2-b (1.1eq, 1.39g, 178.04g / mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g / mol, 14.23mmol) into ethylene glycol diamine ether (80g, 20 times the quality of compound 2-a) and water (80g, 20 times the quality of compound 2-a), stir and mix and then add tri(o-toluene Base) phosphine (5%eq, 0.11g, 304.37g / mol, 0.36mmol) and palladium (II) acetate (1%eq, 0.02g, 224.51g / mol, 0.07mmol), after warming up to reflux for 15h, the The organic phase was separated, washed with water, and concentrated under reduced pressure to obtain a crude product, which was subjected to column chromatography to obtain an organic electroluminescent material (6) (3.79 g, yield 86.5%), MS (EI): 616 (M+).

Embodiment 3

[0062]

[0063] The synthetic method of organic compound (7) is as follows:

[0064]

[0065] Compound 3-a (4g, 563.45g / mol, 7.12mmol), compound 3-b (1.1eq, 1.55g, 198.03g / mol, 7.83mmol) and sodium carbonate (2eq, 1.51g, 105.99g / mol, 14.23mmol) into ethylene glycol diamine ether (80g, 20 times the quality of compound 3-a) and water (80g, 20 times the quality of compound 3-a), stir and mix and then add tri(o-toluene Base) phosphine (5%eq, 0.11g, 304.37g / mol, 0.36mmol) and palladium (II) acetate (1%eq, 0.02g, 224.51g / mol, 0.07mmol), after warming up to reflux for 15h, the The organic phase was separated, washed with water, and concentrated under reduced pressure to obtain a crude product, which was subjected to column chromatography to obtain an organic electroluminescent material (7) (3.9 g, yield 86.1%), MS (EI): 636 (M+).

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Abstract

The invention discloses a triphenyl-based organic compound, an organic electroluminescent material and a device, the structural formula of the triphenyl-based organic compound is shown in the following formula (I): R is any one of hydrogen, deuterium, halogen atom, cyano, substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C30 aromatic group, and substituted or unsubstituted C5-C30 heteroaromatic group; X, Y and Z are respectively and independently CH or N, and at least one of X, Y and Z is N; m, s and n are respectively and independently 0 or 1; the organic compound is used as the electron transport layer so that the driving voltage of the device can be greatly reduced, the consumption of electric energy is greatly reduced, the luminous efficiency is remarkably improved, and in addition, the service life of the organic light-emitting device is remarkably prolonged by reducing the driving voltage.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a triphenylene-based organic compound, an organic electroluminescence material and a device. Background technique [0002] Organic light emitting diode (OLED) was first discovered in the laboratory by Chinese-American professor Deng Qingyun. Since then, people have launched the development and research of OLED. OLEDs have two major application areas: lighting and displays. [0003] OLED is a current-type organic light-emitting device, which is a phenomenon of luminescence caused by injection and recombination of carriers, and the luminous intensity is proportional to the injected current. Under the action of an electric field in the OLED, the holes generated by the anode and the electrons generated by the cathode will move, inject into the hole transport layer and the electron transport layer respectively, and migrate to the light emitting layer. When the tw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/24C07D405/10C07D409/10C07D403/10C07D239/26C09K11/06H01L51/50H01L51/54
CPCC07D405/10C07D409/10C07D403/10C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092C07D251/24C09K2211/1059H10K85/615H10K85/624H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/16Y02E10/549
Inventor 钱超许军
Owner NANJING TOPTO MATERIALS CO LTD
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