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Heterocyclic compound and use thereof

A kind of technology of heterocyclic compound and heteroaryl, applied in the field of organic electroluminescent materials

Inactive Publication Date: 2019-06-11
AAC TECH NANJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, blue luminescent materials with good luminescence lifetime and emission efficiency have yet to be developed

Method used

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  • Heterocyclic compound and use thereof
  • Heterocyclic compound and use thereof
  • Heterocyclic compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0110] The specific embodiment of the present invention also provides the above-mentioned preparation method, which is synthesized through the following general synthetic route:

[0111]

[0112] The bromides of anthracene derivatives are chemically coupled with organoborides of dibenzofuran or dibenzothiophene derivatives according to the Suzuki-Miyaura reaction using tetrakis(triphenylphosphine)palladium(0) as a catalyst.

[0113] in,

[0114] Ar 1 selected from hydrogen atoms, substituted or unsubstituted C6-C30 aryl groups;

[0115] R 1 -R 8 each independently selected from a hydrogen atom, a deuterium atom, a C1-C8 alkyl group, a substituted or unsubstituted C6-C30 aryl group;

[0116] X is selected from O or S;

[0117] R 9 -R15 Each is independently selected from a hydrogen atom, a deuterium atom, a C1-C8 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group.

[0118] Synthetic example:

[0119] ...

Embodiment 1

[0121] The preparation of embodiment 1:L2

[0122]

[0123] After adding a certain amount of D2 and K2 into the three-necked flask, install a mechanical stirring bar, feed nitrogen for 20 minutes, and add catalyst Pd (PPh 3 ) 4 0.25-3mol%, 0.018mol of 2M alkali solution, heated to reflux, reacted for 5-10 hours, suction filtered after reaction, washed with toluene and ethanol. After recrystallization from xylene, a powder with a purity of more than 99% is obtained. In order to further improve the purity of L2, a vacuum sublimation apparatus is used to perform one or more sublimation, and an L2 product with a purity greater than 99.5% can be obtained.

[0124] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0125] 1H NMR (400MHZ, DMSO-d6):

[0126] 7.32ppm(12H,p), 7.38-7.41ppm(4H,t), 7.48ppm(2H,d), 7.54ppm(2H,d), 7.63-7.71ppm(14H,m).

Embodiment 2

[0127] The preparation of embodiment 2:L5

[0128]

[0129] After adding a certain amount of D5 and K5 into the three-necked flask, install a mechanical stirring bar, feed nitrogen for 20 minutes, and add catalyst Pd (PPh 3 ) 4 0.25-3mol%, 0.018mol of 2M alkali solution, heated to reflux, reacted for 5-10 hours, suction filtered after reaction, washed with toluene and ethanol. After recrystallization from xylene, a powder with a purity of more than 99% is obtained. In order to further improve the purity of L5, a vacuum sublimation apparatus is used to carry out one or more sublimation, and the L5 product with a purity greater than 99.5% can be obtained.

[0130] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0131] 1 H NMR (400MHZ, DMSO-d6):

[0132] 7.19-7.22ppm (4H, q), 7.32ppm (12H, t), 7.41-7.48ppm (8H,p), 7.67ppm (8H,p).

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Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses a heterocyclic compound and use thereof. The heterocyclic compound provided by the invention has a structure of a formula (B) and has the advantages of serving as a blue-light or dark-blue-light luminescent material for an organic electroluminescent device and overcoming the defects of an existing blue-lightluminescent material; and the compound, as a luminescent material, has a closely matched hole-electron transmission rate, which is conducive to improving the luminescence efficiency of the material and device stability. In addition, the compound has extremely high bond dissociation energy, which is conducive to prolonging the driving life of a display device. Moreover, the compound has an extremely high radiative transition rate constant, which is conducive to prolonging the driving life of an organic light-emitting diode device.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to a heterocyclic compound and its application. Background technique [0002] In recent years, organic light emitting diodes with electroluminescent properties have been intensively researched and developed. In the basic structure of an organic light emitting diode element, a thin film layer containing a luminescent material is disposed between a first electrode and a second electrode, and light emission is obtained from the luminescent material by applying a voltage to the element. [0003] Due to the above-mentioned autonomous light-emitting characteristics of organic light-emitting diode elements, compared with liquid crystal displays, they have the advantages of high pixel visibility and no need for backlight sources, so they are extremely suitable as flat-panel display elements. Lightweight and fast response are the advantages of organic light-emitting diode ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91C07D333/76C09K11/06H01L51/50H01L51/54
Inventor 谢再锋
Owner AAC TECH NANJING
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