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Organic electroluminescent compound containing phenanthrene and application thereof

An electroluminescent device and luminescent technology, which is applied in organic chemistry, luminescent materials, circuits, etc., can solve the problems of unbalanced number of electrons and holes in the luminescent layer, low electron mobility, low electron mobility, etc., and achieve high thermal And the effects of chemical stability, high carrier mobility, and improved transfer and delivery capabilities

Pending Publication Date: 2022-04-15
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In OLED materials, since most organic electroluminescent materials transport holes faster than electrons, it is easy to cause an imbalance in the number of electrons and holes in the light-emitting layer, so that the efficiency of the device is relatively low.
Tris(8-hydroxyquinoline)aluminum (Alq 3 ) has been widely studied since its invention, but its electron mobility as an electron transport material is still very low, and due to its inherent characteristics of degradation, there will be a voltage drop in devices using it as an electron transport layer At the same time, due to the lower electron mobility, a large number of holes enter the Alq 3 In the layer, the excess holes radiate energy in a non-luminescent form, and when used as an electron-transporting material, its application is limited due to its green-emitting properties.

Method used

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  • Organic electroluminescent compound containing phenanthrene and application thereof
  • Organic electroluminescent compound containing phenanthrene and application thereof
  • Organic electroluminescent compound containing phenanthrene and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0024] Step ①:

[0025]

[0026]

[0027] Under a nitrogen atmosphere, weigh 5 mmol of raw material A and dissolve it in 80 mL of tetrahydrofuran, then add 5 mmol of raw material B and 0.1 mmol of tetrakis(triphenylphosphine) palladium, stir the mixture, then add 40 mL of an aqueous solution containing 10 mmol of potassium carbonate, The mixed solution of the above reactants is heated to reflux at a reaction temperature of 70-90°C for 5-20 hours. After the reaction, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, the obtained residue was purified by silica gel column to obtain Intermediate A;

[0028] Step ②:

[0029]

[0030] Under a nitrogen atmosphere, weigh 5 mmol of intermediate A and dissolve it in 80 mL of tetrahydrofuran, then add 5 mmol of raw material C and 0.2 mmol of tetrakis(triphenylphosphine) palladium, stir the mixture, and ...

specific Embodiment 1

[0038]

[0039] 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 48 h 33 N 3 S: 683.24, Found: 683.20. C 48 h 33 N 3 S element analysis theoretical value: C, 84.30; H, 4.86; N, 6.14. Elemental analysis found values: C, 84.33; H, 4.88; N, 6.20.

specific Embodiment 2

[0041]

[0042] 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 46 h 31 N 5 O: 669.25, Found: 669.3. C 46 h 31 N 5O element analysis theoretical value: C, 82.49; H, 4.67; N, 10.46. Elemental analysis found values: C, 82.50; H, 4.72; N, 10.41.

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PUM

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Abstract

The invention relates to an organic electroluminescent compound containing phenanthrene. The structure of the organic electroluminescent compound is shown as a formula (I). Wherein Ar1 is selected from a substituted or unsubstituted arylene group of C6 to C30; ar2 is selected from hydrogen, a substituted or unsubstituted aryl group of C6-C30 or a substituted or unsubstituted heteroaryl group of C6-C30; z1-Z5 are respectively and independently selected from N or CH; and X is selected from O, S, N-CH3 or N-Ph. The phenanthrene-containing organic electroluminescent compound is used for an organic electroluminescent device, the efficiency and the service life are greatly improved compared with those of a known OLED material, particularly, the driving voltage of the device is remarkably reduced, and the phenanthrene-containing organic electroluminescent compound is an electron transport material with excellent performance. As mentioned above, the compound provided by the invention has high thermal stability, and the prepared organic electroluminescent device has long service life.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to an organic electroluminescent compound containing phenanthrene and its application. Background technique [0002] Organic electroluminescence (OLED, Organic Light Emission Diodes) device technology has the advantages of thinness, self-luminescence, wide viewing angle, low energy consumption, high efficiency, rich colors, fast response speed, wide application temperature, low driving voltage, flexible and bendable and It has unique advantages such as transparent display panels and environmental friendliness, and has a wide range of application prospects. Generally composed of two opposing electrodes and at least one layer of organic electroluminescent compound interposed between the two electrodes, charges are injected into the organic layer formed between the anode and cathode to form electrons and holes Yes, causing light emission from organic compounds with fluoresce...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07D403/04C07D405/14C07D409/14C07D401/14C09K11/06H01L51/50H01L51/54
Inventor 田帅孙加宝
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD