Preparation method for organic compound by using seven-element ring as core structure and application thereof on OLED

A technology of organic compounds and core structures, applied in the field of organic optoelectronic materials, can solve the problems of shifting emission wavelengths, unsuitable for large-scale production, and difficult to guarantee the stability of devices, and achieve the effect of high luminous efficiency

Inactive Publication Date: 2019-04-23
烟台九目化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, small molecular compounds are easy to crystallize after forming a film, and sometimes even form exciplexes with other organic materials. For this reason, in the initial research, the method of doping is often used, but the slight change of doping concentration will lead to luminescence. The shift of the wavelength makes it difficult to guarantee the stability of the device, and the doping method is not suitable for large-scale production. Therefore, the research on the improvement of the molecular structure of the compound has begun, and an organic compound with superior luminous efficiency has been developed. It has also become an urgent problem to be solved

Method used

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  • Preparation method for organic compound by using seven-element ring as core structure and application thereof on OLED
  • Preparation method for organic compound by using seven-element ring as core structure and application thereof on OLED
  • Preparation method for organic compound by using seven-element ring as core structure and application thereof on OLED

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of compound 1

[0025]

[0026] The specific synthetic route of compound 1:

[0027]

[0028] Under the protection of nitrogen, to a 500ml three-necked flask, add 27.9g compound A (100mmol), 17.3g compound B (110mmol), 3.8g cuprous iodide (20mmol), 42.4g tripotassium phosphate (200mmol), 200g di Toluene was heated to reflux for 7 hours, and no compound A was traced by TLC. After the reaction is complete, cool down to 30°C, filter, rinse with 40ml*3 xylene, wash the filtrate with water 150g*4 to pH=7, and pass through a silica gel column under normal pressure after drying. After passing through the column, wash the silica gel column with 40ml*2 xylene. After rinsing, combine the eluent and the passing liquid to remove the solvent under reduced pressure. Afterwards, 21.8 g of compound 1 was obtained, yield: 63.6%, HPLC: 99.25%.

[0029] HPLC-MS: The theoretical molecular weight of compound 1 is 355.4, and the actual detection result mo...

Embodiment 2

[0030] Embodiment 2: the synthesis of compound 5

[0031]

[0032] Synthetic route of compound 5

[0033]

[0034] Under the protection of nitrogen, to a 500ml three-necked flask, add 27.9g compound A (100mmol), 22.8g compound C (110mmol), 2.9g cuprous bromide (20mmol), 42.4g tripotassium phosphate (200mmol), 200g di Toluene was heated to reflux for 6 hours, and no compound A was traced by TLC. After the reaction is complete, cool down to 30°C, filter, rinse with 40ml*3 xylene, wash the filtrate with water 150g*4 to pH=7, and pass through a silica gel column under normal pressure after drying. After passing through the column, rinse the silica gel column with 40ml*2 xylene. After rinsing, combine the eluent and the column liquid to remove the solvent under reduced pressure. After removing the solvent, add 180g of toluene and 150g of ethanol to recrystallize three times 31.7 g of compound 1 was obtained, yield: 78.0%, HPLC: 99.78%.

[0035] HPLC-MS: The theoretical mol...

Embodiment 3

[0036] Embodiment 3: the synthesis of compound 22

[0037]

[0038] Synthetic route of compound 22

[0039]

[0040] Under the protection of nitrogen, to a 500ml three-necked flask, add 27.9g compound A (100mmol), 30.9g compound D (110mmol), 7.6g cuprous iodide (40mmol), 27.6g potassium carbonate (200mmol), 200g o-di Chlorobenzene, heated to reflux for 6 hours, traced by TLC to no compound A. After the reaction is complete, cool down to 30°C, filter, rinse with 40ml*3 toluene, wash the filtrate with 150g*3 water until pH=7, remove the solvent, add 250g toluene to dissolve, pass through a silica gel column under normal pressure, and pass through the column, 50ml toluene *2 Rinse the silica gel column. After rinsing, combine the eluent and the column solution to remove the solvent under reduced pressure. After desolventization, add 230g ethyl acetate and 230g petroleum ether to recrystallize twice. After drying, 33.5g of compound 22 is obtained. , Yield: 69.7%, HPLC: 99....

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PUM

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Abstract

The invention relates to a preparation method for an organic compound by using a seven-element ring as a core structure and an application thereof on an OLED, and belongs to the technical field of organic photoelectric materials. The organic compound has better molecular stability. A prepared OLED device has excellent luminous efficiency, and is capable of meeting requirements of a device manufacturer well.

Description

technical field [0001] The invention relates to the preparation of an organic compound with a seven-membered ring as the core structure and its application in OLEDs, belonging to the technical field of organic photoelectric materials. Background technique [0002] Organic Light Emitting Diode (OLED) is referred to as OLED display. Compared with traditional liquid crystal display, OLED display has high brightness, fast response, low power consumption, high contrast, wide viewing angle, full color, wide operating temperature range, etc. , has been applied to mobile phone screens, TV screens, etc., with superior performance, highlighting very superior application prospects in the fields of display and lighting. [0003] When the OLED device is at an appropriate voltage, the positive holes from the hole transport layer and the cathode charges from the electron transport layer will combine in the light-emitting layer to produce OLED electroluminescence. According to different ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/56C07D405/04C07D409/04C07D209/86C07D209/88C07D403/04H01L51/50H01L51/54
CPCC07D209/56C07D209/86C07D209/88C07D403/04C07D405/04C07D409/04H10K85/622H10K85/615H10K85/654H10K85/6576H10K85/6572H10K85/6574H10K50/11H10K50/16
Inventor 鞠亮李海艳李特周继忠于晓艺徐立
Owner 烟台九目化学股份有限公司
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