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Nitrogen heterocyclic compound and organic light-emitting display device

A nitrogen heterocyclic compound and a six-membered heterocyclic technology are applied in the field of organic electroluminescent materials, which can solve the problems of difficulty in developing doping materials, poor molecular thermal stability, low triplet energy level, etc. The effect of macromolecular density, luminous efficiency and lifetime improvement

Active Publication Date: 2018-11-23
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current research status, the commercialization of heavy metal doping materials is mature, and it is difficult to develop alternative doping materials
At the same time, the existing phosphorescent host materials have disadvantages such as low triplet energy level, low molecular density, low glass transition temperature, and poor molecular thermal stability.

Method used

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  • Nitrogen heterocyclic compound and organic light-emitting display device
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  • Nitrogen heterocyclic compound and organic light-emitting display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069]

[0070] In a 250ml round bottom flask, add 2,6-difluoropyridineboronic acid (0.01mol), 3,6-dibromopyrazine (0.012mol) and tetrakis(triphenylphosphine)palladium (0.0006mol) into 15ml tetrahydrofuran THF , add 10ml 2M K 2 CO 3 solution, stirred at a certain speed, and the resulting mixed solution reactant was heated to reflux at a reaction temperature of 80°C for 18 hours; after the reaction was completed, it was cooled to room temperature and 100ml of water was added, and the resulting mixture was filtered and washed three times in 25ml of dichloroethane , and finally dried over anhydrous magnesium sulfate. The resulting residue was further separated and purified through a silica gel column to obtain an intermediate product M2.

[0071] In a 250ml round bottom flask, add intermediate product M2 (0.01mol), dimethylacridine (0.035mol), K 2 CO 3 (0.076mol) and dimethyl sulfoxide (20ml), stirred at a certain speed, fed with nitrogen, and heated to reflux at 150°C for...

Embodiment 2

[0074]

[0075] In a 250ml round bottom flask, add 2,6-difluoropyridineboronic acid (0.02mol), 3,6-dibromopyrazine (0.012mol) and tetrakis(triphenylphosphine)palladium (0.0006mol) into 15ml tetrahydrofuran THF , add 10ml 2M K 2 CO 3 solution, stirred at a certain speed, and the resulting mixed solution reactant was heated to reflux at a reaction temperature of 80°C for 18 hours; after the reaction was completed, it was cooled to room temperature and 100ml of water was added, and the resulting mixture was filtered and washed three times in 25ml of dichloroethane , and finally dried over anhydrous magnesium sulfate. The resulting residue was further separated and purified by a silica gel column to obtain an intermediate product M3.

[0076] In a 250ml round bottom flask, add intermediate product M3 (0.01mol), diphenylamine (0.045mol), K 2 CO 3 (0.076mol) and dimethyl sulfoxide (20ml), stirred at a certain speed, fed with nitrogen, and heated to reflux at 150°C for 12h. A...

Embodiment 3

[0079]

[0080]

[0081] In a 250ml round bottom flask, 2-phenyl, 6-fluoropyridineboronic acid (0.02mol), 3,6-dibromo, 5-phenylpyrazine (0.012mol) and tetrakis (triphenylphosphine) palladium ( 0.0006mol) into 15ml tetrahydrofuran THF, add 10ml 2M K 2 CO 3 solution, stirred at a certain speed, and the resulting mixed solution reactant was heated to reflux at a reaction temperature of 80°C for 18 hours; after the reaction was completed, it was cooled to room temperature and 100ml of water was added, and the resulting mixture was filtered and washed three times in 25ml of dichloroethane , and finally dried over anhydrous magnesium sulfate. The resulting residue was further separated and purified through a silica gel column to obtain an intermediate product M5.

[0082] In a 250ml round bottom flask, add intermediate product M5 (0.01mol), dimethylacridine (0.025mol), K 2 CO 3 (0.076mol) and dimethyl sulfoxide (20ml), stirred at a certain speed, fed with nitrogen, and hea...

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Abstract

The invention relates to a nitrogen heterocyclic compound, which has a structure shown in a formula (I), wherein X1-X5 are C atoms or N atoms, and at least two of X2-X4 are N atoms; m and n are respectively and independently selected from 0, 1 or 2, and the sum of the m and the n greater than or equal to 1; R1-R5 are the same or different, and R1-R5 are respectively and independently selected fromsubstituted or unsubstituted C6-C60 aryls, substituted or unsubstituted C10-C60 fused aryls, substituted or unsubstituted C4-C60 five-membered heterocyclic rings, substituted or unsubstituted C6-C60six-membered heterocyclic rings. The nitrogen heterocyclic compound, as a main material or a CPL layer material in an electroluminescent device, has a higher triplet state energy level ET and a largermolecular density as well as higher glass transition temperature and molecular thermal stability, effectively improves the balanced migration of carriers, widens an exciton recombination region, effectively improves the light extraction efficiency, and greatly improves the luminous efficiency and service life of the device, thus being better applied in the technical field of electroluminescent devices. The invention also provides an organic light emitting display device.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a novel nitrogen-heterocyclic compound light-emitting host material and the application of the material in organic light-emitting display devices. Background technique [0002] As a new generation of display technology, organic electroluminescent materials (OLED) have the advantages of ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. It has been widely used in industries such as flat panel display, flexible display, solid state lighting and vehicle display. [0003] According to the luminescence mechanism, it can be divided into two types: electrofluorescence and electrophosphorescence. Fluorescence is the radiation decay transition of singlet excitons, and phosphorescence is the light emitted by triplet excitons deca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D413/14C07D487/04C07D417/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C07D413/14C07D417/14C07D487/04C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1059H10K85/6572H10K85/657H10K50/12H10K50/00
Inventor 张磊王湘成高威牛晶华刘营邓东阳罗学强安平
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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