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A compound for organic light-emitting and its application

A compound and organic technology, applied in the field of organic light-emitting compounds, can solve the problems that the service life of TADF devices does not meet the display application industry standard, the efficiency reduces the service life, and the display application is not expected, so as to achieve good industrialization prospects and improve thermal stability , Improve the effect of exciton utilization

Active Publication Date: 2022-04-12
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, most TADF emissive materials exhibit very broad emission spectra, making them undesirable for display applications
Additionally, the lifetime of TADF devices still does not meet industry standards for display applications
TADF devices also have serious efficiency reduction and lifetime issues at high brightness

Method used

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  • A compound for organic light-emitting and its application
  • A compound for organic light-emitting and its application
  • A compound for organic light-emitting and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0028] This embodiment provides the preparation method for the above-mentioned organic light-emitting compound.

[0029] ① Synthesis of intermediate A:

[0030]

[0031] Raw materials (10mmol), p-dibromobenzene (8mmol, log) were added to a 100mL two-necked flask, and copper iodide (0.6mmol), potassium carbonate (10mmol), 1,10-phenanthroline ( 0.6mmol), 50mL of DMF, reacted at 155°C for 48 hours; the mixture was extracted three times with ethyl acetate; the extract was washed with MgSO 4 Dried, filtered, concentrated and subjected to column chromatography (silica gel, from 100:1PE / CH 2 Cl 2 up to 5:1PE / CH 2 Cl 2 Gradient elution) to obtain a white solid, i.e. intermediate A, the yield is shown in the table below:

[0032] Table 1

[0033]

[0034] ②Synthesis of the target product:

[0035]

[0036] Add intermediate A (1mmol) and carbazole derivatives (2mmol) to the three-necked flask respectively, and dissolve them with toluene; add Pd in ​​turn 2 (dba) 3 (0.0...

specific Embodiment 1

[0038]

[0039] Add intermediate A to the three-necked flask 1 (1mmol), carbazole derivatives (2mmol), and dissolved with toluene; add Pd sequentially 2 (dba) 3 (0.02mmol), tri-tert-butylphosphine (0.02mmol), sodium tert-butoxide (2.2mmol); N 2 Bubbling for 10 minutes and under an inert atmosphere, the mixed solution of the above reactants was reacted at a reaction temperature of 95-110°C for 10-24 hours. After cooling, the mixture was extracted three times with ethyl acetate; the extract was washed with MgSO 4 Dried, filtered, concentrated and subjected to column chromatography (silica gel, from pure PE to 10:1PE / CH 2 Cl 2 Gradient elution) to obtain the target product.

[0040] Further purification using reverse phase column chromatography with acetonitrile as eluent gave a white solid whose structure was confirmed by mass spectrometry, HRMS Calcd for C 43 h 24 N 2 o 3 : 616.18, Found: 616.2. C 43 h 24 N 2 o 3 Theoretical value of elemental analysis: C, 83.75...

specific Embodiment 2

[0042]

[0043] Add intermediate A to the three-necked flask 2 (1mmol), carbazole derivatives (2mmol), and dissolved with toluene; add Pd sequentially 2 (dba) 3 (0.02mmol), tri-tert-butylphosphine (0.02mmol), sodium tert-butoxide (2.2mmol); N 2 Bubbling for 10 minutes and under an inert atmosphere, the mixed solution of the above reactants was reacted at a reaction temperature of 95-110°C for 10-24 hours. After cooling, the mixture was extracted three times with ethyl acetate; the extract was washed with MgSO 4 Dried, filtered, concentrated and subjected to column chromatography (silica gel, from pure PE to 10:1PE / CH 2 Cl 2 Gradient elution) to obtain the target product.

[0044] Further purification using reverse phase column chromatography with acetonitrile as eluent gave a white solid whose structure was confirmed by mass spectrometry, HRMS Calcd for C 38 h 24 N 2 O: 524.19, Found: 524.20. C 38 h 24 N 2 O element analysis theoretical value: C, 87.00; H, 4.61; ...

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Abstract

The present invention relates to a compound for organic luminescence, the structure of which is shown in formula (I): wherein, X is selected from one of carbonyl, oxygen atom or sulfur atom; said formula (I) is also passed The C-C bond is connected with a substituent group. The compound of the present invention destroys the crystallinity of molecules by linking different aromatic substituent groups, avoids the strong aggregation between molecules and improves the glass transition temperature of the material, and the good thermal stability of the material helps to improve the performance of the device. life. The compound of the invention has good application effect in OLED devices and has good industrialization prospect.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound for organic light emission and its application. Background technique [0002] Organic electroluminescence (OLED, Organic Light Emission Diodes) device technology can be used not only to manufacture new display products, but also to make new lighting products, and has a very broad application prospect. It generally consists of two opposing electrodes and at least one layer of organic light-emitting compound interposed between the two electrodes. Charges are injected into the organic layer formed between the anode and cathode to form pairs of electrons and holes, causing light emission from organic compounds having fluorescent or phosphorescent properties. [0003] Thermally activated delayed fluorescence (TADF) materials are the third-generation organic light-emitting materials developed after organic fluorescent materials and organic phosphorescent materials. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/10C07D413/10C07D417/10C07D491/153C09K11/06H01L51/54H01L51/50
CPCC07D413/10C07D491/153C07D417/10C07D401/10C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037H10K85/6572H10K85/657H10K50/11
Inventor 田帅
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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