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Nitrogen-containing heterocyclic organic compound and application thereof

A technology of organic compounds and mixtures, applied in the field of electroluminescent materials, can solve the problems of device performance and lifespan that need to be improved, and achieve the effects of improving luminous efficiency and lifespan, improving electroluminescent efficiency and device lifespan, and reducing manufacturing costs.

Active Publication Date: 2021-04-30
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the obtained device performance and lifetime still need to be improved

Method used

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  • Nitrogen-containing heterocyclic organic compound and application thereof
  • Nitrogen-containing heterocyclic organic compound and application thereof
  • Nitrogen-containing heterocyclic organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0195]

[0196] Synthesis of Intermediate 1-3: Dissolve 1-1 (20.0g) and 1-2 (43.8g) in dry DMF, add cesium carbonate (38.46g), and react at 140°C for 8h. After cooling, most of the solvent was distilled off under reduced pressure, the residual reaction liquid was washed with water and extracted, and the organic phase was rotary evaporated to remove the solvent and then recrystallized to obtain intermediate 1-3.

[0197] Synthesis of Compound 1: Intermediate 1-3 (10.0g), Pd(PCy 3 ) 2 Cl 2 (CAS 78655-99-9, 1.2g), isovaleric acid (1.1g), and cesium carbonate (10.0g) were added to 100ml of dry DMAC, and stirred at 170°C for 6h under a nitrogen atmosphere. After cooling, most of the solvent was distilled off under reduced pressure, extracted and washed with water to separate the liquids, and the organic phase was rotary evaporated to remove the solvent and then recrystallized to obtain compound 1. MS (ASAP):602.

Embodiment 2

[0199]

[0200] Synthesis of Intermediate 2-3: Intermediate 2-1 (20.0g), 2-2 (16.6g), DMAP (3.17g) were dissolved in dry DMSO, and cesium carbonate (33.0g) was added, under nitrogen Under the atmosphere, it was heated to 100°C for 8h. After cooling, most of the solvent was distilled off under reduced pressure. The residual reactant was washed with water and extracted, and the organic phase was rotary evaporated to remove the solvent and then recrystallized to obtain intermediate 2-3.

[0201] The synthesis of material 2 refers to the synthesis of material 1 in Example 1, except that 1-3 is replaced by 2-3. MS (ASAP): 588.

Embodiment 3

[0203]

[0204] Synthesis of intermediate 3-2: 3-1 (15.0g), biboronic acid pinacol ester (9.3g), Pd(dppf)Cl 2 ([1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, 1.2g), potassium acetate (4.9g) were added to 1,4-dioxane, under nitrogen atmosphere, 100 ℃ reaction 8h. After cooling, most of the solvent was distilled off under reduced pressure, and the remaining reaction liquid was washed and extracted with water, and the organic phase was rotary evaporated to remove the solvent, and then recrystallized to obtain intermediate 3-2.

[0205] Synthesis of intermediate 3-4: 3-2 (10.0g), 3-3 (5.2g), Pd(PPh 3 ) 4 (Tetrakis(triphenylphosphine)palladium, 0.8g) and potassium carbonate (4.2g) were added to 1,4-dioxane, and an appropriate amount of water was added. The reaction was carried out at 100°C for 8h under nitrogen atmosphere. After cooling, most of the solvent was distilled off under reduced pressure, and the remaining reaction solution was washed and extracted wit...

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Abstract

The invention relates to the field of electroluminescence, in particular to a nitrogen heterocyclic ring-containing organic compound, a high polymer containing the nitrogen heterocyclic ring-containing organic compound, a mixture and a composition, and an application of the nitrogen heterocyclic ring-containing organic compound in organic electronic devices. The organic compound provided by the invention can be used as a host material to be applied to an electroluminescent device, especially an OLED device. The organic compound according to the present invention can be coordinated with a suitable object, particularly a phosphorescent object or a TADF light-emitting body, thereby improving the light-emitting efficiency and prolonging the service life of the organic compound as an electroluminescent device. The invention provides a solution of a light-emitting device which is low in manufacturing cost, high in efficiency, long in service life and low in roll-off.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on October 28, 2019, with the application number 201911029851.8 and the title of the invention "A nitrogen-containing heterocyclic organic compound and its application in organic electronic devices", The entire contents of which are incorporated by reference in this application. technical field [0002] The invention relates to the field of electroluminescent materials, in particular to a nitrogen-containing heterocyclic organic compound and its application. Background technique [0003] Organic optoelectronic materials have diverse synthesis, relatively low manufacturing cost, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential for applications in optoelectronic devices such as flat panel displays and lighting due to their advantages of wide viewing angle, fast response time, low operating volt...

Claims

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Application Information

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IPC IPC(8): C07D487/16C07D471/22C07D519/00C07D513/22C07D491/22C07D487/22C07D495/22C09K11/06H01L51/50H01L51/54
CPCC07D487/16C07D471/22C07D519/00C07D513/22C07D491/22C07D487/22C07D495/22C09K11/06C09K2211/1044C09K2211/1048C09K2211/1051C09K2211/1059C09K2211/1074C09K2211/1077C09K2211/1062C09K2211/1081C09K2211/1092C09K2211/1066C09K2211/1011H10K85/615H10K85/6576H10K85/657H10K85/6572H10K50/171H10K50/18H10K50/16H10K50/15H10K50/17H10K50/11Y02E10/549Y02P70/50
Inventor 张晨萧锡辉李灿楷
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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