Anthraquinone organic electroluminescent material and application thereof

An organic layer, selected technology, applied in the direction of light-emitting materials, organic chemistry, circuits, etc., can solve the problems of light color deviation, unsuitable for display applications, and short life of blue PHOLEDs

Inactive Publication Date: 2019-11-05
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, various types of materials have been reported, among which reports on xanthraquinone compounds can also be seen. In Patent Document 3, a luminescent material about a compound having a diarylamine group introduced into the xanthraquinone skeleton is described. However, the compound compound is a sky-blue light material, which is not suitable for display applications
[0005] At present, the wide band gap of blue phosphorescent materials leads to a short lifespan of blue PHOLEDs, which is one of the reasons that have restricted the further industrialization of PHOLEDs. TADF materials are expected to make breakthroughs in blue light materials, but there are currently blue light devices using doped devices. The problem of serious efficiency roll-off and light color deviation at high current density
Therefore, there is still much room for improvement in the luminescence performance of existing organic electroluminescent materials, and the industry urgently needs to develop new organic electroluminescent materials.

Method used

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  • Anthraquinone organic electroluminescent material and application thereof
  • Anthraquinone organic electroluminescent material and application thereof
  • Anthraquinone organic electroluminescent material and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0061] Preparation of intermediate M1:

[0062] In a 500mL three-necked flask, add 2-fluoro-4-bromobenzonitrile (10g, 50mmol), phenol (4.94g, 52.5mmol) and K 2 CO 3 (13.8g, 100mmol) and DMF (120mL), heated at 140°C for 4 hours under the protection of nitrogen. TLC monitored the reaction to completion. The reaction solution was cooled to room temperature, diluted with toluene (100mL), washed with water (50mL*2), separated to remove the water phase, and the organic phase was dried with anhydrous sodium sulfate and concentrated to a small volume. White solid, filtered to obtain intermediate M1 13.2g.

[0063] Preparation of intermediate M2:

[0064] Intermediate M1 (63g, 229mmol) was dissolved in EtOH (500mL), NaOH (27g, 689mmol) was added, heated to 100°C under nitrogen protection, and refluxed for 5h. TLC monitored until the reaction was complete. After cooling down, filter to obtain a solid. Adjust the system to PH=1 with hydrochloric acid (1N), extract the aqueous phas...

Embodiment approach

[0117] The organic light emitting diode includes a first electrode and a second electrode on the substrate, and an organic material between the electrodes, and a hole transport layer, a light-emitting layer, and an electron transport layer are included between the first electrode and the second electrode.

[0118] The substrate is the substrate used in organic light emitting displays, such as glass, polymer materials, and glass and polymer materials with TFT components.

[0119] The anode material can be indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and other transparent conductive materials, also metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT, and multilayer structures of the above materials.

[0120] The device can also include a hole injection layer positioned between the hole transport layer and the anode, including but not limited to one or more combinations of HI...

Embodiment 1

[0143] The fabrication process of organic electroluminescent devices is as follows:

[0144] The glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent, baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light. Light and ozone cleaning, and bombardment of the surface with a beam of low-energy cations;

[0145] Place the above-mentioned glass substrate with the anode in a vacuum chamber, and evacuate to 1×10 -5 ~9×10 -3 Pa, on the above-mentioned anode layer film vacuum evaporation HI-2 is used as the hole injection layer, the evaporation rate is 0.1nm / s, and the evaporation film thickness is 10nm;

[0146] Vacuum-deposit HT-2 on the hole injection layer as the hole transport layer of the device, the evaporation rate is 0.1nm / s, and the total film thickness is 40nm;

[0147] Va...

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PUM

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Abstract

The invention discloses an anthraquinone organic electroluminescent material and application thereof. A general formula compound is shown in a formula (1) in the specification, and in the formula (1),Z is selected from O or S; X1-X8 are independently selected from CR1 or N, wherein R1 is selected from a structure shown in a formula (2) in the specification, or selected from hydrogen, alkyl, arylor heterocyclic aryl, adjacent R1 groups can form a ring, and at least one of R1 groups is selected from the structure (2) shown in the formula (2); in the formula (2), Y1-Y8 are independently selected from CR2 or N, and at least one of the Y1-Y8 is selected from N; R2 is selected from hydrogen, alkyl, aryl or heterocyclic aryl, and adjacent R2 groups can form a ring; L is selected from single bonds, arylidene or heterocyclic arylidene; and when two or more R1 groups are selected from the formula (2), the selected L groups in the formula (2) are not single bonds at the same time. The compoundshows excellent device performance and stability when serving as the light-emitting material in an organic light-emitting device (OLED), and meanwhile the OLED adopting the general formula compound iswithin the scope of right protection.

Description

[0001] The invention relates to an organic compound, which can be used as a luminescent material for an organic electroluminescent device; the invention also relates to the application of the compound in an organic electroluminescent device. Background technique [0002] The earliest dyes used in OLEDs are pure organic small molecule light-emitting materials. Devices based on these materials have long lifetimes and low efficiency roll-off. However, the material can only use 25% of S1 to emit light, and 75% of T1 can only be lost through non-radiative transitions due to spin prohibition. In 1998, Forrest et al. from Princeton University reported for the first time PHOLEDs based on T1 emission. Utilizing the spin-orbit coupling effect caused by the heavy metal Pt atoms, T1 can emit light effectively at room temperature, so that the internal quantum efficiency of 100% can be theoretically achieved. However, also because of the presence of heavy metals, the phosphorescent dyes a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D487/04C07D519/00C07D491/147C09K11/06H01L51/54
CPCC07D471/04C07D487/04C07D519/00C07D491/147C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1037C09K2211/1044H10K85/653H10K85/615H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/6572
Inventor 高文正杜倩张春雨任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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