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Compound with spirofluorene as core, preparation method thereof, and application of compound in organic light-emitting device

A compound and luminescence technology, applied in the fields of electric solid-state devices, electrical components, organic chemistry, etc., can solve different problems and achieve the effects of polymer thermal stability, good photoelectric performance, and high glass transition temperature

Inactive Publication Date: 2019-09-24
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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  • Compound with spirofluorene as core, preparation method thereof, and application of compound in organic light-emitting device
  • Compound with spirofluorene as core, preparation method thereof, and application of compound in organic light-emitting device
  • Compound with spirofluorene as core, preparation method thereof, and application of compound in organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Embodiment 1 is the preparation of the compound taking spirofluorene as core

Embodiment 1-1

[0100] The preparation of embodiment 1-1 compound 3

[0101]

[0102] Step 1: Infuse nitrogen into a 250mL three-necked flask, add 0.01mol raw material A1, 0.015mol raw material B1, dissolve in a mixed solvent (90mL toluene, 45mL ethanol), and then add 0.03mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4 , heated to reflux for 15 hours, sampling point plate, natural cooling after the reaction was complete, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate C1 with a HPLC purity of 94.1% and a yield of 76.6%;

[0103] Step 2: Introduce nitrogen into a 250mL three-necked flask, add 0.01mol intermediate C1, 0.015mol raw material B2, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150mL toluene, heated to 95°C, refluxed for 24 hours, sampled and spotted on the plate, cooled naturally after the reaction was complete, ...

Embodiment 1-2

[0105] The preparation of embodiment 1-2 compound 5

[0106]

[0107] Step 1: Infuse nitrogen into a 250mL three-neck flask, add 0.01mol raw material A2, 0.015mol raw material B1, dissolve with a mixed solvent (90mL toluene, 45mL ethanol), and then add 0.03mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4 , heated to reflux for 15 hours, sampling point plate, natural cooling after the reaction was complete, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate C2 with a HPLC purity of 95.4% and a yield of 73.0%;

[0108] Step 2: Introduce nitrogen into a 250mL three-necked flask, add 0.01mol intermediate C2, 0.015mol raw material B2, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150ml toluene, heated to 95°C, refluxed for 24 hours, sampled and spotted on the plate, cooled naturally after the reaction was complete...

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Abstract

The invention relates to a compound with spirofluorene as a core, a preparation method thereof, and an application of the compound in an organic light-emitting device. The spirofluorene is adopted as the core of the compound, and is connected with an electron-donating group and an electron-withdrawing group in order to easily achieve electron blocking, so the high efficiency of the device can be easily obtained. The compound provided by the invention has a high glass transition temperature, a high molecular thermal stability, a suitable HOMO emerge level and a suitable LUMO energy level, and can effectively improve the photoelectric performances of the OLED and the lifetime of the OLEs by device structure optimization.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with spirofluorene as the core, its preparation method and its application in organic electroluminescent devices. Background technique [0002] Organic Light Emission Diodes (OLED) device technology can be used not only to manufacture new display products, but also to make new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] 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 positi...

Claims

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Application Information

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IPC IPC(8): C07D213/38C07D215/12C07D217/02C07D235/18C07D241/42C07D251/24C07D263/57C07D401/10C07D403/10C07D405/10C07D405/12C07D409/10C07D413/10C07D421/10C07D471/04H01L51/54
CPCC07D239/26C07D251/24C07D241/42C07D471/04C07D263/57C07D213/38C07D215/12C07D401/10C07D413/10C07D405/10C07D409/10C07D421/10C07D403/10C07D235/18C07D217/02C07D405/12H10K85/622H10K85/624H10K85/633H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 庞羽佳李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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