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Anthraquinone organic electroluminescent material and application thereof

An organic layer, selected technology, applied in the fields of luminescent materials, organic dyes, organic chemistry, etc., can solve problems such as efficiency roll-off, achieve the effect of improving device life, avoiding aggregation, and improving RISC rate

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, the main problem of TADF materials is the serious efficiency roll-off of doped devices at high current densities. 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. 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
Comparison scheme
Effect test

preparation example Construction

[0054] Preparation of intermediate M1:

[0055] In a 500mL three-necked flask, add 2-fluoro-4-bromobenzonitrile (10g, 50mmol), thiophenol (5.78g, 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 13.5g.

[0056] Preparation of intermediate M2:

[0057] Intermediate M1 (66.4g, 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 aqueou...

Embodiment approach

[0115] 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.

[0116] The substrate is a substrate used in organic light emitting displays, such as glass, polymer materials, glass and polymer materials with TFT components, and the like.

[0117] 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.

[0118] 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 combinatio...

Embodiment 1

[0141] The fabrication process of organic electroluminescent devices is as follows:

[0142] 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;

[0143] Place the above-mentioned glass substrate with the anode in a vacuum chamber, and evacuate to 1×10 -5 ~9×10 -3 Pa, HI-2 is vacuum-deposited on the above-mentioned anode layer film as a hole injection layer, the evaporation rate is 0.1nm / s, and the evaporation film thickness is 10nm;

[0144] 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;

[0145] On top of t...

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PUM

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Abstract

The invention discloses an anthraquinone general formula compound and application thereof. The general formula compound is shown in a formula (1) in the specification, and in the formula (1), n is aninteger of 1-2; when n is 2, two L groups in the formula (1) can be different, and two Ar groups in the formula (1) can be different; X1-X8 are independently selected from C, CR or N, when any one ortwo of X1-X8 represent C, the C atom is connected with L, and R is selected from a hydrogen atom, alkyl of C1-C10, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; the Ar is selected from substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; and the L is selected from single bonds, substituted or unsubstituted C6-C20 arylidene, or substituted or unsubstituted C3-C20 heterocyclic arylidene. The compound shows excellent device performance and stability when serving as a main body material in a light-emitting layerof an organic light-emitting device (OLED), and meanwhile the OLED adopting the general formula compound is within the scope of right protection.

Description

[0001] The invention relates to an organic compound which can be used as a luminescent material of an organic electroluminescent device; the invention also relates to the application of the compound in the organic electroluminescent device. Background technique [0002] The earliest dyes used in OLEDs are pure organic small molecule light-emitting materials. Devices based on such materials have long life 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. Currently, most phosphorescent dyes are based on Ir complexes. The hexahedral configur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/10C07D409/14C07D335/16C07D495/04C07D519/00C07D413/14C07D417/14C07D491/048C07D487/04C07D495/14C07D409/12C09B57/00C09K11/06H01L51/50H01L51/54
CPCC07D409/10C07D409/14C07D335/16C07D495/04C07D519/00C07D413/14C07D417/14C07D491/048C07D487/04C07D495/14C07D409/12C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1092C09K2211/1088C09K2211/1011C09K2211/1033C09K2211/1037H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 高文正杜倩张春雨任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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