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Novel bipolar green phosphorescent host material and OLED light-emitting device containing same

A green phosphorescence, host material technology, applied in the field of OLED light-emitting devices, can solve the problems of quenching device efficiency, high price, roll-off, etc., and achieve the effect of improving efficiency and service life, and improving transmission capacity

Active Publication Date: 2021-02-02
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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  • Novel bipolar green phosphorescent host material and OLED light-emitting device containing same
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  • Novel bipolar green phosphorescent host material and OLED light-emitting device containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

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

[0044] (1)

[0045]

[0046] 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 NaHCO3 (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 liquid separation, and concentrated under reduced pressure Purified by chromatography to obtain compound 2 (2-chloro-[1,2,4]triazolo[1,5-a]pyridine) (6.82g, yield 76.2%), MS (EI): 153 (M + ).

...

Embodiment 2

[0063]

[0064] For the synthesis of the novel bipolar green phosphorescent host material (4), steps (1)-(4) are the same as in Example 1, and the rest of the steps are as follows:

[0065] (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 11(3-bromo-9-(4,6-di([1,1'-biphenyl]-4-yl)-1,3,5-triazin-2-yl)-9H- carbazole) (1eq, 9.54g, 628.13g / 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), stir and mix and then add three (o-tolyl) phosphine (3%eq, 0.14g, 304.37g / mol, 0.46mmol) and palladium (II ) (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 obtained a new type of bipolar green phosphorescence...

Embodiment 3

[0069]

[0070] For the synthesis of the novel bipolar green phosphorescent host material (20), steps (1)-(4) are the same as in Example 1, and the rest of the steps are as follows:

[0071] (5)

[0072]

[0073] 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 12 (9-(4-(anthracen-9-yl)-6-phenyl-1,3,5-triazin-2-yl)-3-bromo-9H-carbazole) (1eq, 8.75 g, 576g / 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, compound 20 times the mass of 7), 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, 0.017 g, 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 obtained a novel bipolar green phosphorescent h...

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Abstract

The invention discloses a novel bipolar green phosphorescent host material and an OLED light-emitting device containing the same. The structural general formula of the novel bipolar green phosphorescent host material is shown in the specification. The novel bipolar green phosphorescent host material can greatly reduce the driving voltage of the device, greatly reduce the consumption of electric energy and significantly improve the luminous efficiency. In addition, by reducing the driving voltage, the service life of the organic light-emitting device is remarkably prolonged.

Description

technical field [0001] The invention relates to the field of organic electroluminescence materials, and specifically relates to a novel bipolar green phosphorescence 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%. Ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/50H01L51/54
CPCC07D471/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088H10K85/615H10K85/654H10K85/6572H10K85/6574H10K50/12
Inventor 钱超许军
Owner NANJING TOPTO MATERIALS CO LTD