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Pyrazine derivative and application thereof in organic electroluminescence device

A compound, C6-C60 technology, applied in the field of organic electroluminescence display

Inactive Publication Date: 2016-11-09
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported thermally activated delayed fluorescence materials can only be prepared by doping due to the aggregation fluorescence quenching effect in the solid state.

Method used

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  • Pyrazine derivative and application thereof in organic electroluminescence device
  • Pyrazine derivative and application thereof in organic electroluminescence device
  • Pyrazine derivative and application thereof in organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1, the preparation of compound SLC-1

[0074]

[0075] The first step: the preparation of intermediate Q-1

[0076]

[0077] 10g (46.9mmol) of 4-bromophenylacetone aldehyde was dissolved in 100ml of methanol-water, 5g (46.9mmol) of diaminomaleic cyanide was added, stirred at room temperature for 1 hour, 0.5g of potassium tert-butoxide was added, stirred Reacted for 24 hours, filtered, and the filtrate was concentrated to dryness under reduced pressure, separated and purified by silica gel column, and concentrated to dryness under reduced pressure to obtain 11.6 g of yellow solid with a yield of 87%.

[0078] The second step: the preparation of compound formula SLC-1

[0079]

[0080] Mix 10g (35mmol) of intermediate Q-1, 11g (38.6mmol) of 9-phenyl-3-carbazoleboronic acid, 7.4g (69.8mmol) of sodium carbonate, and then add 202mg (0.17mmol) of Pd(PPh 3 ) 4 Catalyst and 100mL of toluene, then add 20mL of ethanol and 20mL of water, under the protection...

Embodiment 2

[0081] Embodiment 2, the preparation of compound SLC-41

[0082]

[0083] The first step: the preparation of intermediate Q-1

[0084]

[0085] 10g (36mmol) of p-bromophenyl bromoethanone was dissolved in 80ml of dry tetrahydrofuran, and under nitrogen protection, 3.9g (36mmol) of o-phenylenediamine was added, and then 0.5ml of pyridine was added, stirred at room temperature for 24 hours, filtered, The filtrate was concentrated to dryness under reduced pressure, separated and purified by a silica gel column to obtain 9.4 g of a yellow solid with a yield of 92%.

[0086] The second step: the preparation of compound formula SLC-41

[0087]

[0088] Mix 5g (17.5mmol) of intermediate Q-1, 5.5g (19.3mmol) of 9-phenyl-3-carbazole boronic acid, and 3.7g (34.9mmol) of sodium carbonate, and then add 100mg (0.086mmol) of Pd (PPh 3 ) 4 Catalyst and 60mL of toluene, then add 20mL of ethanol and 20mL of water, under the protection of nitrogen, raise the temperature and reflux ...

Embodiment 3

[0089] Embodiment 3, the preparation of compound formula SLC-83

[0090]

[0091] The synthetic operation refers to the second step of Example 2, 5g (17.5mmol) of intermediate Q-1, 7.8g (19.3mmol) of intermediate FPC-1 replaces the 9-phenyl-3- Carbazole boronic acid was separated and purified on a silica gel column to obtain 8.5 g of a yellow solid with a yield of 86%. HRMS: C 41 h 29 N 3 , standard molecular weight 563.24, test result 564.26.

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Abstract

The invention discloses a pyrazine derivative and application thereof in an organic electroluminescence device. The structure of the material is as shown in formula I in the specification. By adopting the material, the start voltage of the organic electroluminescence device prepared from the material can be reduced, the current efficiency and the electroluminescence efficiency of the device can be improved, the service life of the device can be prolonged, and moreover, the material has the characteristics of being simple in synthesis and purification method, applicable to large-scale production and the like, and is an ideal option as a material of the organic electroluminescence device. As the light-emitting layer of an OLED (Organic Light-Emitting Diode) device made of the fluorescent material is high in fluorescence efficiency and good in stability, the fluorescence efficiency and the service life of the device can both meet the requirement of practical utilization.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent display, and relates to pyrazine derivatives and their application in organic electroluminescent devices. Background technique [0002] Organic electroluminescence (referred to as OLED) and related research As early as 1963, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display And other advantages, can be widely used in flat panel displays and surface light sources, so it has been wid...

Claims

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Application Information

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IPC IPC(8): C07D403/10C07D413/14C07D405/14C07D409/14C07D403/14C07D417/14C07D401/14C07D471/04C07D487/04C09K11/06H01L51/54
CPCC09K11/06C07D401/14C07D403/10C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14C07D471/04C07D487/04C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1048H10K85/6565H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/11H10K50/00
Inventor 曹建华王士波董梁华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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