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Preparation method and applications of hexatomic dinitrogen heterocyclic derivatives containing four identical substituent groups

A technology for diazoheterocycles and derivatives, applied in the field of preparation of six-membered dizazaheterocycle derivatives

Inactive Publication Date: 2016-12-21
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 applications of hexatomic dinitrogen heterocyclic derivatives containing four identical substituent groups
  • Preparation method and applications of hexatomic dinitrogen heterocyclic derivatives containing four identical substituent groups
  • Preparation method and applications of hexatomic dinitrogen heterocyclic derivatives containing four identical substituent groups

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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PUM

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Abstract

The invention discloses a preparation method and applications of hexatomic dinitrogen heterocyclic derivatives containing four identical substituent groups, and belongs to the field of application technology of luminescent materials in preparation of organic light-emitting devices. According to the preparation method, pyrazine and pyridazine are taken as electron acceptors of luminescent materials; the periphery of the electron acceptors is connected with electron donors such as carbazole, phenoxazine, and 9,9-dimethyl-9,10-dihydracridine; frontal orbital overlapping degree of HOMO and LUMO is adjusted, so that luminescent materials with thermally activated delayed fluorescence (TADF) characteristics are obtained. At room temperature, the hexatomic dinitrogen heterocyclic derivatives possess strong absorption at ultraviolet-visible region, a dilute solution of the hexatomic dinitrogen heterocyclic derivatives is capable of emitting strong fluorescence, the wavelength of emission peaks ranges from 450 to 615nm in the blue light-orange light range, the hexatomic dinitrogen heterocyclic derivatives can be applied to organic light-emitting devices as luminescent materials. According to devices based on compound M2, turn-on voltage is 3.9V, the maximum brightness 3846cdm<2> is achieved at a voltage of 12V; and the maximum luminous efficiency 17.4cdA<1> and the maximum power efficiency 12.21mW<1> are achieved when electric current density is 0.06mAcm<2>(4.5V).

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 Applications(China)
IPC IPC(8): C07D403/14C07D413/14C07D401/14C09K11/06H01L51/54
CPCC09K11/06C07D401/14C07D403/14C07D413/14C09K2211/1029C09K2211/1044C09K2211/1033H10K85/654H10K85/657H10K85/6572
Inventor 李久艳隋凯刘迪
Owner DALIAN UNIV OF TECH
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