A kind of organic electroluminescent material of xanthene spiroazanthone, its preparation method and application

A technology of xanthene spiroazanthone and xanthene spiroazanthone, which is applied in the field of organic electroluminescence, can solve the problem of not meeting the performance improvement requirements of OLED devices and market demand, and increasing the difficulty of high-efficiency TADF main materials , low device performance and other issues, to achieve good industrialization prospects, suppress quenching effects, and good photoelectric performance

Active Publication Date: 2020-05-05
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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  • A kind of organic electroluminescent material of xanthene spiroazanthone, its preparation method and application
  • A kind of organic electroluminescent material of xanthene spiroazanthone, its preparation method and application
  • A kind of organic electroluminescent material of xanthene spiroazanthone, its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The synthesis of embodiment 1 compound C01

[0035]

[0036] 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%.

[0037] 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

[0038] The synthesis of embodiment 2 compound C05

[0039]

[0040] Referring to Example 1, the target product C05 was obtained with a yield of 76.6%.

[0041] 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

[0042] The synthesis of embodiment 3 compound C08

[0043]

[0044] Referring to Example 1, the target product C08 was obtained with a yield of 76.1%.

[0045] 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 in particular relates to an organic electroluminescent material of xanthene spiroazanthone series, a preparation method and an application thereof. In the present invention, the xanthene ring and the azanthone ring are connected through a spiro carbon, which can effectively reduce the degree of conjugation between the xanthene ring and the azanthone ring, so that it has suitable HOMO and LUMO energy levels; The modification of the xanthene ring can further change the distorted structure of the xanthene ring and the azaxanthone ring, enhance the molecular rigidity and asymmetry, and the rigid structure can effectively inhibit the structural relaxation, enhance the stability of the material, and improve the photoelectric performance ; the asymmetric structure can greatly suppress the intermolecular interactions and form a highly disordered molecular packing pattern in its solid-state film. The compound of the invention has a good application effect in OLED light-emitting devices and has a good industrialization 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 Patents(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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