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Nitrogen-containing organic compounds and application of compounds in organic light emission diodes

A technology of organic compounds and compounds, applied in organic chemistry, electrical solid devices, electrical components, etc., can solve different problems and achieve the effects of not being easy to gather, preventing energy loss, and good industrialization prospects

Inactive Publication Date: 2019-07-02
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Nitrogen-containing organic compounds and application of compounds in organic light emission diodes
  • Nitrogen-containing organic compounds and application of compounds in organic light emission diodes
  • Nitrogen-containing organic compounds and application of compounds in organic light emission diodes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The synthesis of embodiment 1 compound 1

[0051] The synthetic steps of compound are as follows:

[0052]

[0053] In a 500mL three-neck flask, under the protection of nitrogen, add 0.03mol raw material A-1, 0.03mol raw material B-1, 250mL toluene and stir to mix, then add 0.09mol potassium tert-butoxide, 0.0015mol Pd 2 (dba) 3 , heated to 110°C, reflux reaction for 24 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain compound 1. The HPLC purity was 99.3%, and the yield was 76.3%;

[0054] Elemental analysis structure (molecular formula C 41 h 23 N 3 O): theoretical value C, 85.84; H, 4.04; N, 7.33; found value: C, 85.82; H, 4.05; N, 7.34. MS m / z: 573.42[M+H] + , theoretical value: 573.65.

Embodiment 2

[0055] The synthesis of embodiment 2 compound 13

[0056] The synthetic steps of compound are as follows:

[0057]

[0058]

[0059] In a 500mL three-neck flask, under the protection of nitrogen, add 0.03mol raw material B-2, 0.03mol p-dibromobenzene, 250mL toluene and stir to mix, then add 0.09mol potassium tert-butoxide, 0.0015mol Pd 2 (dba) 3 , heated to 110°C, and refluxed for 24 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to reduced-pressure rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain intermediate C-1;

[0060] In a 250mL three-neck flask, under the protection of nitrogen, add 0.02mol of intermediate C-1, 0.03mol of pinacol diborate, 0.05mol of potassium carbonate, 0.002mol of Pd(PPh 3 ) 4 and 100ml of toluene / water (volume ratio=5:1), stir and mix, heat to 80°C, react for 24 hours, take a sample point plate, it shows that there is no intermediate C-1 remaining, and the re...

Embodiment 3

[0063] The synthesis of embodiment 3 compound 26

[0064] The synthetic steps of compound are as follows:

[0065]

[0066] In a 500mL three-neck flask, under the protection of nitrogen, add 0.03mol raw material A-1, 0.03mol raw material B-3, 250mL toluene and stir to mix, then add 0.09mol potassium tert-butoxide, 0.0015mol Pd 2 (dba) 3 , heated to 110°C, and refluxed for 24 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain compound 26. The HPLC purity was 99.3%, and the yield was 76.3%;

[0067] Elemental analysis structure (molecular formula C 41 h 23 N 3 O): theoretical value C, 85.84; H, 4.04; N, 7.33; found value: C, 85.82; H, 4.05; N, 7.34. MS m / z: 573.42[M+H] + , theoretical value: 573.65.

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Abstract

The invention discloses nitrogen-containing organic compounds and an application of the compounds in organic light emission diodes. The compounds provided by the invention use azaspirofluorene as a mother nucleus and have stronger rigidity, so that the compounds have the characteristics that molecules are not easy to crystallize or aggregate and the film forming performance is good; the azaspirofluorene mother nucleus has stronger electron-withdrawing ability, and the branch chains has electron-donating ability, so that the compounds have good bipolar transmission properties; in addition, thecompounds have a high triplet state energy level, so that the compounds can effectively block energy loss; therefore, after the compounds are applied to the organic light emission diodes, the currentefficiency, power efficiency and external quantum efficiency of the organic light emission diodes are greatly improved; and at the same time, the service life of the organic light emission diodes is obviously improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a nitrogen-containing organic compound and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, and the positive ...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D471/04C09K11/06H01L51/54
CPCC07D519/00C07D471/04C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1033C09K2211/1096C09K2211/1014H10K85/615H10K85/636H10K85/633H10K85/657H10K85/6574H10K85/6572
Inventor 叶中华李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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