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Cyano quinoxaline red light thermal excitation delayed fluorescence material, synthesis method and application thereof

A technology of cyanoquinoxalines and delayed fluorescence, which is applied in the field of electroluminescent materials, can solve the problems of enhanced intermolecular interaction, concentration quenching, and increased polarity, and achieve the purpose of inhibiting intermolecular interaction and inhibiting quenching. The effect of destroying and improving the transmission ability

Pending Publication Date: 2021-08-03
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In order to realize red-light TADF materials, it is usually necessary to further enhance the interaction between the donor and the acceptor, and a stronger interaction tends to increase the polarity of the material and enhance the intermolecular interaction, resulting in serious concentration quenching. off

Method used

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  • Cyano quinoxaline red light thermal excitation delayed fluorescence material, synthesis method and application thereof
  • Cyano quinoxaline red light thermal excitation delayed fluorescence material, synthesis method and application thereof
  • Cyano quinoxaline red light thermal excitation delayed fluorescence material, synthesis method and application thereof

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preparation example Construction

[0081] In the present invention, a preparation method of the cyanoquinoxaline-based red-light thermally excited delayed fluorescence material is also provided, and the material is prepared from raw materials including halogenated aromatic ketone compounds and diaminophthalonitrile compounds , preferably, the method comprises the following steps:

[0082] Step 1. Add the halogenated aromatic ketone compound and the reactant I into the solvent, stir and react to obtain the intermediate I.

[0083] The halogenated aromatic ketones are selected from halogenated phenyl monoketones or halogenated phenyl diketones, preferably 1-halogenated phenyl-2-halogenated alkan-1-ones or halogenated phenyl- 1,2-Diketone, more preferably 1-halophenyl-2-haloethan-1-one or halophenylethanedione, such as 2-bromo-1-(4-bromophenyl)ethyl -1-one, 1,2-bis(4-bromophenyl)ethane-1,2-dione.

[0084] The reactant I is a diaminophthalonitrile compound or an aromatic amine compound I. When the reactant I is ...

Embodiment 1

[0184] 10mmol of 4,5-diaminophthalonitrile, 10mmol of 2-bromo-1-(4-bromophenyl)ethan-1-one, 50ml of water and 0.9g of hexadecyltrimethyl ammonium bromide, stirred and reacted at 100°C for 12 hours, then poured into ice water, filtered with suction, and washed the resulting solid with absolute ethanol to obtain 2-(4-bromophenyl)quinoxaline-6,7- Dicarbonitrile.

[0185] Mix 2mmol 2-(4-bromophenyl)quinoxaline-6,7-dicarbonitrile with 2.5mmol diphenylamine, 0.06mmol tridibenzylideneacetone dipalladium, 6mmol cesium carbonate, 0.3mmol tri-tert-butylphosphine Mix, add 10mL xylene as a solvent, reflux reaction at 135°C for 12h, and then pour into ice water. Extract with water and dichloromethane (the volume ratio of the two is 1:1), combine the organic layers, and remove the organic solvent after drying to obtain a crude product, which is purified by column chromatography with a mixed solvent of petroleum ether and dichloromethane as eluent (The volume ratio of the two is 1:2), to o...

Embodiment 2

[0204] According to the synthesis method of compound 1 in Example 1, compound 2 was prepared. The only difference is: 4,5-diaminophthalonitrile is replaced by 2,3-diaminoterephthalonitrile.

[0205] The compound 2 that obtains is carried out proton nuclear magnetic resonance spectrum analysis, test data is: 1 H NMR (TMS, CDCl 3 ,400MHz): δ=9.54(s,1H),8.24(d,J=8.9Hz,2H),8.16(d,J=7.6Hz,1H),8.07(d,J=7.6Hz,1H),7.37 (t,J=7.9Hz,4H),7.25–7.21(m,4H),7.21–7.16(m,4H).

[0206] The obtained compound IV was subjected to thermogravimetric analysis, and the test data were as follows: Figure 4 shown by Figure 4 It was found that the cracking temperature of the obtained compound was 422°C.

[0207] According to the preparation method of the electroluminescent red light device in Example 1, the mixture of compound 2 and CBP (wherein the mass fraction of compound 2 is 20%) was used as the light-emitting layer material to prepare the electroluminescent red light device.

[0208] The stru...

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Abstract

The invention provides a cyano quinoxaline red light thermal excitation delayed fluorescence material. The efficient red light TADF material is prepared by designing a molecular structure, modifying molecules with aromatic amine groups or aromatic phosphine oxide groups, improving the carrier transmission capability and inhibiting the intermolecular interaction on the premise of not influencing the emission wavelength of the material and adjusting the molecular configuration, electrical properties and the like of the material. Therefore, the electro-red light device with excellent comprehensive performance is obtained.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, in particular to a thermally excited delayed fluorescent material based on dicyanoquinoxaline compounds. Background technique [0002] Organic light-emitting diodes (Organic Light Emitting Diodes, OLEDs) are favored for their outstanding advantages such as ultra-light and ultra-thin, flexible and flexible, fast response, energy saving and environmental protection, and have become a new generation of flat panel display technology and lighting field. stand out. The traditional first-generation organic electroluminescent materials are fluorescent materials, because they only use singlet excitons to emit light, so the internal quantum efficiency can only reach 25% in theory. Phosphorescent materials based on heavy metal complexes can simultaneously utilize singlet and triplet excitons to achieve 100% internal quantum efficiency and become the second generation of electroluminesc...

Claims

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Application Information

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IPC IPC(8): C07D241/42C07F9/6509C09K11/06H01L51/50H01L51/54
CPCC07D241/42C07F9/650994C09K11/06C09K2211/1044C09K2211/1007C09K2211/1014Y02B20/00
Inventor 韩春苗李哲许辉
Owner HEILONGJIANG UNIV
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