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Nitrogen-doped diimide compound, and organic light-emitting display device

A technology of azadiimide and heterodiimide, which is applied in the field of organic electroluminescent materials, and can solve problems such as the difficulty in developing heavy metal doped materials

Inactive Publication Date: 2018-12-14
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 doped materials is mature, and it is difficult to develop alternative heavy metal doped materials

Method used

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  • Nitrogen-doped diimide compound, and organic light-emitting display device
  • Nitrogen-doped diimide compound, and organic light-emitting display device
  • Nitrogen-doped diimide compound, and organic light-emitting display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091]

[0092] In a 250ml round bottom flask, 9,9-dimethylacridine borate (0.01mol), 1-bromo-3-chlorobenzene (0.012mol) and tetrakis(triphenylphosphine)palladium (0.0006mol) Add 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 M1.

[0093] In a 250ml round bottom flask, add intermediate product M1 (0.01mol), intermediate reactant A1 (0.015mol), 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 fo...

Embodiment 2

[0096]

[0097] In a 250 ml round bottom flask, phenoxazine borate (0.01 mol), 1-bromo-3-chlorobenzene (0.012 mol) and tetrakis(triphenylphosphine)palladium (0.0006 mol) were added to 15 ml of tetrahydrofuran THF, Add 10ml of 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.

[0098] In a 250ml round bottom flask, add intermediate product M5 (0.01mol), intermediate reactant A5 (0.012mol), K 2 CO 3 (0.076mol) and dimethyl sulfoxide (20ml), stirred at a certain speed, fed with nitrogen, and heated to reflux...

Embodiment 3

[0101]

[0102] In a 250ml round bottom flask, carbazole borate (0.02mol), 2-chloro-4,6-dibromobenzene (0.012mol) and tetrakis(triphenylphosphine) palladium (0.0006mol) were added to 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 M14.

[0103] In a 250ml round bottom flask, add intermediate product M14 (0.02mol), intermediate reactant A14 (0.025mol), K 2 CO 3 (0.076mol) and dimethyl sulfoxide (20ml), stirred at a certain speed, fed with nitrogen, and heated to reflux at ...

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Abstract

The invention relates to a nitrogen-doped diimide compound. The compound is provided with a structure as shown in Formula (I), wherein X<1>, X<2>, X<3> and X<4> are carbon or nitrogen atoms, and at least one is a nitrogen atom; L is a linker or linkers, and D is a donor or donors; m is the number of the linker(s) L, n is the number of the donor(s) D, m is 0, 1 or 2, and n is 1 or 2; R is preferredto be a substituted or unsubstituted C6-C40 aryl group, or a substituted or unsubstituted C5-C40 heteroaryl group; and L is preferred to be a substituted or unsubstituted C3-C20 heterocyclic group (groups), a substituted or unsubstituted C6-C40 aryl group (groups), or a substituted or unsubstituted C5-C40 heteroaryl group (groups). The nitrogen-doped diimide compound provided by the invention isused as a principal material or a CPL layer material of an electroluminescent device, achieves a higher triplet energy level E<T>, a larger molecular density, a higher glass transition temperature andhigher molecular heat stability, and can effectively improve balance migration of carriers, expand the exciton recombination domain, effectively improve the optical extraction efficiency, enhance thelight-emitting efficiency of the device, and prolong the service life of the device. The invention further 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 azadiimide luminescent host material and the application of the material in organic electroluminescent 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 luminescent mechanism, organic electroluminescent materials can be divided into two types: electroluminescent luminescent materials and electrophosphorescent luminescent materials. emitted light. According to the spin quantum statistical theory, the format...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D487/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C07D487/04C09K2211/1037C09K2211/1033C09K2211/1044C09K2211/1007C09K2211/1029H10K85/654H10K85/657H10K85/6572
Inventor 张磊王湘成高威牛晶华卢艳范昌煊黄高军安平
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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