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A green phosphorescent host material and an OLED light-emitting device containing the material

A technology of host materials and light-emitting devices, applied in the direction of light-emitting materials, electric solid devices, semiconductor devices, etc., can solve the problems of unfavorable mass production of high-efficiency OLED devices, quenching device efficiency, high price, etc., and achieve an increase in glass transition temperature and thermal stability, improve stability and service life, reduce planarity and crystallinity

Active Publication Date: 2021-12-03
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the second generation of OLEDs based on phosphorescent materials still faces many problems: (1) transition metals such as Os, Ir, and Pt, which are often used in the light-emitting layer, are expensive, which is not conducive to mass production of high-efficiency OLED devices; The triplet-triplet excitons are prone to quenching phenomenon at high currents, which makes the device efficiency roll off seriously
Therefore, OLED light-emitting devices with high efficiency and long life are usually the result of the optimal combination of device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures

Method used

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  • A green phosphorescent host material and an OLED light-emitting device containing the material
  • A green phosphorescent host material and an OLED light-emitting device containing the material
  • A green phosphorescent host material and an OLED light-emitting device containing the material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] The synthesis method of green phosphorescence host material (1) comprises the following steps:

(1)

[0044]

[0045] Compound 1 ((Z)-N'-hydroxy-N-(pyridin-2-yl)carbamimidic chloride) (10g, 171g / mol, 1eq, 58.48mmol) was added to anhydrous THF (100g, the mass of compound 1 10 times), the temperature was lowered to 0°C under the protection of nitrogen, and trifluoroacetic anhydride (1.1eq, 210g / mol, 64.33mmol, 13.51g) was added dropwise and continued to stir for 30min, then slowly returned to room temperature, and continued to react for 3h. saturated NaHCO 3 (150g, 15 times the mass of compound 1) solution quenched, then extracted with methyl tert-butyl ether (150g, 15 times the mass of compound 1), dried over anhydrous sodium sulfate after separation, concentrated under reduced pressure and then column chromatography Purified to obtain compound 2 (2-chloro-[1,2,4]triazolo[1,5-a]pyridine) (6.82g, yield 76.2%), MS (EI): 153 (M + ).

(2)

[0046]

[0...

Embodiment 2

[0057]

[0058] The synthesis method of green phosphorescence host material (2) comprises the following steps:

[0059] Steps 1-4 are the same as in Example 1, and the steps are as follows:

(5)

[0060]

[0061] Compound 7 ((9-([1,2,4]triazolo[1,5-a]pyridin-2-yl)dibenzo[b,d]furan-4-yl)boronic acid) (5g, 329g / mol , 15.19mmol), compound 9 (9-(3-([1,1'-biphenyl]-3-yl)quinoxalin-2-yl)-3-bromo-9H-carbazole) (1eq, 7.97g, 525g / mol, 15.19mmol) and sodium carbonate (2eq, 3.22g, 105.99g / mol, 30.38mmol) were added to ethylene glycol diamine ether (100g, 20 times the mass of compound 7) and water (100g, 20 times the mass of compound 7 mass), stir and mix and then add three (o-tolyl) phosphine (3%eq, 0.14g, 304.37g / mol, 0.46mmol) and palladium (II) acetate (0.5%eq, 0.017g, 224.51g / mol, 0.075mmol), after heating up to reflux for 15h, the organic phase was separated, washed with water, concentrated under reduced pressure, and then subjected to column chromatography to obtain the ...

Embodiment 3

[0063]

[0064] The synthesis method of green phosphorescence host material (4) comprises the following steps:

[0065] Steps 1-4 are the same as in Example 1, and the steps are as follows:

(5)

[0066]

[0067] Compound 7 ((9-([1,2,4]triazolo[1,5-a]pyridin-2-yl)dibenzo[b,d]furan-4-yl)boronic acid) (5g, 329g / mol , 15.19mmol), Compound 10 (9-(3-([1,1'-biphenyl]-4-yl)quinoxalin-2-yl)-3-bromo-9H-carbazole) (1eq, 7.97g, 525g / mol, 15.19mmol) and sodium carbonate (2eq, 3.22g, 105.99g / mol, 30.38mmol) were added to ethylene glycol diamine ether (100g, 20 times the mass of compound 7) and water (100g, 20 times the mass of compound 7 mass), stir and mix and then add three (o-tolyl) phosphine (3%eq, 0.14g, 304.37g / mol, 0.46mmol) and palladium (II) acetate (0.5%eq, 0.017g, 224.51g / mol, 0.075mmol), after heating up to reflux for 15h, the organic phase was separated, washed with water, concentrated under reduced pressure, and then subjected to column chromatography to obtain the...

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Abstract

The invention discloses a green phosphorescent host material and an OLED light-emitting device containing the material. The general structural formula is as follows: the green phosphorescent host material of the invention can greatly reduce the driving voltage of the device and greatly reduce the consumption of electric energy , Significantly improved luminous efficiency. In addition, by reducing the driving voltage, the lifetime of the organic electroluminescent device is significantly improved.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a green phosphorescent host material and an OLED light-emitting device containing the material. 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] At present, research on OLEDs at home and abroad has made significant progress. The first-generation OLEDs based on the use of fluorescent materials in the light-emitting layer only use singlet excitons to emit light, and their internal quantum efficiency (IQE) is only 25%. The second-generation OLED of metal phosphorescent materials makes the radiation of triplet excitons possible through spin-orbit coupling, and the theoretical IQE can reach 100%. However, the second-generatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D405/14C07D409/14C09K11/06H01L51/50H01L51/54
CPCC07D471/04C07D405/14C07D409/14C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1011H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K50/11
Inventor 钱超许军
Owner NANJING TOPTO MATERIALS CO LTD
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