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Preparation method and application of a class of six-membered dinitroheterocyclic derivatives containing four identical substituents

A technology for bis-nitroheterocycles and derivatives, applied in the field of preparation of six-membered bis-aza-heterocycle derivatives

Inactive Publication Date: 2019-01-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The future trend is to transmit a large amount of information and images on a lightweight carrier, and today's flat-panel displays can no longer meet the demand

Method used

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  • Preparation method and application of a class of six-membered dinitroheterocyclic derivatives containing four identical substituents
  • Preparation method and application of a class of six-membered dinitroheterocyclic derivatives containing four identical substituents
  • Preparation method and application of a class of six-membered dinitroheterocyclic derivatives containing four identical substituents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of derivative M1

[0044]

[0045] Add 1.69g (10.10mmol) carbazole into a 250ml three-necked flask, then add 100mL N,N-dimethylformamide as a reaction solvent, and stir on a magnetic stirrer for 10min. Under the condition of ice bath, 0.49g (20.19mmol) NaH was added to the reaction flask in batches, and the stirring was continued for 1h. 0.50g (2.30mmol) of 3,4,5,6-tetrachloropyridazine was dissolved in 20ml of N,N-dimethylformamide, and added dropwise to the reaction system. After the addition was complete, under nitrogen protection, Reaction at 60°C for 15h. After the reaction is over, pour the reaction solution into 150ml of dilute hydrochloric acid with a concentration of 10% to quench, filter under reduced pressure, wash with water, and dry the crude product with petroleum ether and ethyl acetate (PE:EA=10:1) Perform column chromatography as the mobile phase to remove impurities, and then use pure dichloromethane (DCM) to flush the ...

Embodiment 2

[0046] Embodiment 2: the synthesis of derivative M2

[0047] method 1)

[0048]

[0049]Add 1.35g (8.08mmol) carbazole into a 250ml three-neck flask, then add 100mL N,N-dimethylformamide as a reaction solvent, and stir on a magnetic stirrer for 10min. Under the condition of ice bath, 0.39g (16.16mmol) NaH was added to the reaction flask in batches, and the stirring was continued for 1h. 0.40g (1.84mmol) of 2,3,5,6-tetrachloropyrazine was dissolved in 20ml of N,N-dimethylformamide, and added dropwise to the reaction system. After the addition, under nitrogen protection, 60 Reaction at ℃ for 15h. After the reaction is over, pour the reaction solution into 150ml of dilute hydrochloric acid with a concentration of 10% to quench, filter under reduced pressure, wash with water, and dry the crude product with petroleum ether and ethyl acetate (PE:EA=10:1) Perform column chromatography as the mobile phase to remove impurities, and then use pure dichloromethane (DCM) to flush the...

Embodiment 3

[0053] Both method (1) and method (2) in Example 3 can obtain the target product M2.

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Abstract

A class of preparation methods and applications containing four similar bases with the same replacement base, which belongs to the application technology field of light -emitting materials in the application technology of preparing mechanical electrical lighting devices.This derivative is an electronic receptor with pyrazine and pyrazine as a luminous material. It connects electronic supplies such as Kagazazo, Poinizine, 9,9‑ Trinomy ‑ 9,10‑ dihydrine.By adjusting the overlapping level of the cutting -edge orbit between HOMO and Lumo, it is expected to obtain some light -emitting materials with armal delayed fluorescent (TADF) nature.At room temperature, these derivatives can be seen strongly in the ultraviolet zone, and their dilute solution is launching strong fluorescence. The light emitting peak is between 450‑615 nanometer and belongs to the blue light ‑ orange light range.Device.For components M2, the opening voltage is 3.9 V, and when the voltage reaches 12V, it reaches a maximum brightness of 3846cdm‑2.When the current density is 0.06macm‑2 (4.5V), the device reaches the maximum luminous efficiency of 17.4cda‑1 and the maximum power efficiency of 12.2LMW‑1.

Description

technical field [0001] The invention relates to a preparation method and application of a class of six-membered dinitrogen heterocyclic derivatives containing four identical substituents, and belongs to the technical field of the application of light-emitting materials in the preparation of organic electroluminescent devices. Background technique [0002] After entering the 21st century of informatization, with the unprecedented prosperity of computer technology and network, the vigorous development of mobile communication and e-commerce, people need a new generation of flat panel displays with better performance and better meeting the needs of future life. The future trend is to transmit a large amount of information and images on a lightweight carrier, and today's flat-panel displays obviously cannot meet the demand. [0003] Organic Light-Emitting Diodes (OLEDs, Organic Light-Emitting Diodes) is a new type of flat panel display technology that has developed rapidly in rec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C07D413/14C07D401/14C09K11/06H01L51/54
CPCC09K11/06C07D401/14C07D403/14C07D413/14C09K2211/1029C09K2211/1044C09K2211/1033H10K85/654H10K85/657H10K85/6572
Inventor 刘迪隋凯
Owner DALIAN UNIV OF TECH
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