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Organic electroluminescent material with xanthene spiroazaanthrones, preparation method and application thereof

A technology of xanthene spiro azaxanthone and xanthene spiro azaxanthone is applied in the field of organic electroluminescence, which can solve the requirement and market demand that cannot meet the performance improvement of OLED devices, and increase the difficulty of high-efficiency TADF host materials , low device performance, etc., to achieve good industrialization prospects, inhibit quenching effect, and good photoelectric performance.

Active Publication Date: 2017-11-07
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In OLEDs devices, the TADF material is usually used as a guest and doped into the host as the light-emitting layer to overcome the low performance of the device due to concentration quenching.
Since TADF materials and their host materials are pure organic molecules, the high degree of similarity in molecular structure and properties can easily lead to the quenching effect between host and guest molecules, which further increases the difficulty of developing efficient TADF host materials.
In recent years, although many TADF host materials have appeared, they are far from meeting the requirements of OLED device performance improvement and market demand, so it is particularly important to develop TADF host materials with better performance

Method used

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  • Organic electroluminescent material with xanthene spiroazaanthrones, preparation method and application thereof
  • Organic electroluminescent material with xanthene spiroazaanthrones, preparation method and application thereof
  • Organic electroluminescent material with xanthene spiroazaanthrones, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthesis of embodiment 1 compound C01

[0033]

[0034] Under nitrogen protection, raw material II (1.53g, 2.5mmol), bromobenzene (0.86g, 5.5mmol), 80mL toluene and 20mL water were added to a 250mL three-necked flask, and then the catalyst tetrakis(triphenylphosphine) palladium (0.029 g, 0.025mmol), acid-binding agent potassium carbonate (1.04g, 7.5mmol). The temperature of the system was raised to reflux for 8 hours, the temperature was naturally lowered to 20-25° C., the liquid was separated, the solvent was removed, and the crude product was crystallized with toluene to obtain 1.12 g of the target product C01 with a yield of 87.5%.

[0035] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 37 h 23 NO 2 , the theoretical value is 513.173, and the test value is 513.173. Elemental analysis (C 37 h 23 NO 2 ), theoretical values ​​C: 86.53, H: 4.51, N: 2.73, O: 6.23. Found values ​​C: 86.53, H: 4.50, N: 2.74, O: 6.23.

Embodiment 2

[0036] The synthesis of embodiment 2 compound C05

[0037]

[0038] Referring to Example 1, the target product C05 was obtained with a yield of 76.6%.

[0039] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 43 h 26 N 2 o 2 , the theoretical value is 602.199, and the test value is 602.199. Elemental analysis (C 43 h 26 N 2 o 2 ), theoretical values ​​C: 85.69, H: 4.35, N: 4.65, O: 5.31. Found values ​​C: 85.70, H: 4.34, N: 4.65, O: 5.31.

Embodiment 3

[0040] The synthesis of embodiment 3 compound C08

[0041]

[0042] Referring to Example 1, the target product C08 was obtained with a yield of 76.1%.

[0043] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 41 h 25 NO 2 , the theoretical value is 563.189, and the test value is 563.181. Elemental analysis (C 41 h 25 NO 2 ), theoretical values ​​C: 87.37, H: 4.47, N: 2.49, O: ,5.68. Found values ​​C: 87.37, H: 4.47, N: 2.49, O: 5.68.

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Abstract

The invention belongs to the field of organic electroluminescence and particularly relates to an organic electroluminescent material with xanthene spiroazaanthrones, a preparation method and an application thereof. The organic electroluminescent material, the preparation method and the application have the advantages that xanthene rings are connected with azaanthrone rings by spirocarbon, the conjugation degree of the xanthene rings and the azaanthrone rings can be effectively reduced, and the HOMO and LUMO energy level is proper; by modification for the xanthene rings, the distorted structures of the xanthene and the azaanthrone rings can be further changed, and the rigidity and the asymmetry of molecules are enhanced; due to the rigid structure, the structure looseness can be effectively inhibited, the stability of the material can be enhanced and the photoelectric property can be improved; and due to the asymmetric structure, the molecular interaction can be greatly inhibited and a highly-disordered molecular stacking mode is formed in a solid-state thin film. The compound has good application effect in OLED (Organic Light-Emitting Diode) luminescent devices and has good industrial prospect.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and in particular relates to an organic electroluminescent material of xanthene spiroazanthone series, a preparation method and an application thereof. Background technique [0002] Since 1987, Organic Light-Emitting Diodes (OLEDs for short) have gradually become the industry-recognized next-generation flat panel display technology. Traditional organic fluorescent materials can only use 25% singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. Although phosphorescent materials enhance the intersystem crossing due to the strong spin-orbit coupling of heavy atom centers, they can effectively use the singlet excitons and triplet excitons formed by electrical excitation to emit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06H01L51/54
CPCC09K11/06C07D491/107C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1011C09K2211/1007H10K85/622H10K85/636H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657
Inventor 张成新李庆巨成良慈振华王崇王柏森
Owner VALIANT CO LTD
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