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Nitrogen heterocyclic compound and preparation method thereof, organic electroluminescent material containing nitrogen heterocyclic compound, luminescent layer and application of luminescent layer

A nitrogen heterocyclic compound and compound technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problem of OLED device performance and luminous efficiency decrease, affecting OLED device luminous efficiency, electron and hole transport imbalance and other problems, to achieve excellent hole transport performance and electron transport performance, improve performance and luminous efficiency, thermal stability and morphological stability.

Active Publication Date: 2020-04-17
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Abstract
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Problems solved by technology

[0003] Today's OLED devices include multiple layers of hole injection layer, hole transport layer, light emitting layer, hole blocking layer, electron transport layer and electron injection layer, and are matched with suitable electrodes. These layers are composed of the following materials : Hole injection material, hole transport material, luminescent material, hole blocking material, electron transport material, and electron injection material, wherein, the OLED light-emitting layer made by doping has advantages in the luminous efficiency of the device, so the luminous Layer materials are often formed by doping guest materials with host materials. Therefore, host materials are an important factor affecting the luminous efficiency and performance of OLED devices; currently, some widely used host materials have good hole transport properties, but as host materials When in use, due to the low glass transition temperature, it is easy to recrystallize, resulting in a decrease in the performance and luminous efficiency of OLED devices
On the other hand, the transport of electrons and holes is unbalanced, the recombination efficiency of excitons is low, the light-emitting area is not ideal, and the roll-off phenomenon of the device is serious during operation, which leads to the energy transfer from the host material to the guest material. low efficiency, reducing device efficiency

Method used

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  • Nitrogen heterocyclic compound and preparation method thereof, organic electroluminescent material containing nitrogen heterocyclic compound, luminescent layer and application of luminescent layer
  • Nitrogen heterocyclic compound and preparation method thereof, organic electroluminescent material containing nitrogen heterocyclic compound, luminescent layer and application of luminescent layer
  • Nitrogen heterocyclic compound and preparation method thereof, organic electroluminescent material containing nitrogen heterocyclic compound, luminescent layer and application of luminescent layer

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0055] This preparation example provides a nitrogen heterocyclic compound C1, which has the following structure:

[0056]

[0057] The preparation method is as follows:

[0058]

[0059] (1) Synthesis of intermediate A1:

[0060] Under nitrogen protection, add tetrabromothiophene (400g, 1.0mol), phenylboronic acid (254g, 2.1mol), potassium carbonate (276g, 2.0mol), toluene 2800mL, ethanol 1200mL into a 10.0L three-neck flask stirred by a thermometer. Mix with 1200mL of water, heat up to 60°C, add catalyst tetrakis(triphenylphosphine)palladium 2.31g (0.002mol), react at 70°C for 6 hours, cool down to room temperature, extract with dichloromethane, wash with water three times, anhydrous sodium sulfate Drying, rotary evaporation to remove most of the solvent, adding n-hexane for recrystallization, and drying to obtain 335g of the main ligand A1 (yield: 85%);

[0061] (2) Synthesis of intermediate B1:

[0062] Under nitrogen protection, in a 5L three-necked flask, add int...

preparation example 2

[0070] This preparation example provides a nitrogen heterocyclic compound C2, which has the following structure:

[0071]

[0072] The preparation method is as follows:

[0073] The difference from Preparation Example 1 is that step (4) is different, and bromobenzene is replaced by 2-bromonaphthalene (the molar weight is unchanged), and the yield is 81%.

[0074] Elemental analysis: (C 48 h 30 N 2 S) Theoretical value: C, 86.46; H, 4.53; N, 4.20; S, 4.81; Measured value: C, 86.47; H, 4.54; N, 4.22; S, 4.83;

[0075] HRMS(ESI)m / z(M + ): theoretical value: 666.84; measured value: 666.90.

preparation example 3

[0077] This preparation example provides a nitrogen heterocyclic compound C3, which has the following structure:

[0078]

[0079] The preparation method is as follows:

[0080] The difference from Preparation Example 1 is that the step (4) is different, and the bromobenzene is replaced by 4-bromobiphenyl (the molar weight is unchanged), and the yield is 83%.

[0081] Elemental analysis: (C 52 h 34 N 2 S) Theoretical value: C, 86.88; H, 4.77; N, 3.90; S, 4.46; Measured value: C, 86.89; H, 4.78; N, 3.92; S, 4.45;

[0082] HRMS(ESI)m / z(M + ): theoretical value: 718.92; measured value: 718.95.

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Abstract

The invention provides a nitrogen heterocyclic compound and a preparation method thereof, an organic electroluminescent material containing the nitrogen heterocyclic compound, a luminescent layer andan application of the luminescent layer . The nitrogen heterocyclic compound comprises a compound with a structure represented by a formula I. When the nitrogen heterocyclic compound provided by the invention is used as a host material, the nitrogen heterocyclic compound has relatively high luminous efficiency, and when the nitrogen heterocyclic compound is used for an OLED device, the overall performance of the device is improved.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting devices, and relates to a nitrogen heterocyclic compound and a preparation method thereof, an organic electroluminescence material containing the same, a light-emitting layer and applications. Background technique [0002] The application of organic light-emitting diodes (OLEDs) in flat panel displays and lighting such as mobile phones and televisions has attracted extensive attention from industry and academia. Compared with traditional light-emitting diodes and liquid crystal displays, it has the advantages of self-illumination, clear and bright, light and thin, fast response, wide viewing angle, low power consumption, wide applicable temperature range, and simple manufacturing process. In particular, the good flexibility can make it be folded, rolled, pasted, and hung like a fantasy display like wallpaper, which is expected to replace liquid crystal displays in the near future. ...

Claims

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Application Information

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IPC IPC(8): C07D491/147C07D495/14C09K11/06H01L51/54
CPCC07D495/14C07D491/147C09K11/06C09K2211/1051C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1048H10K85/626H10K85/615H10K85/654H10K85/657H10K85/6572
Inventor 张玉祥张恒龚明明冉小信丁欢达陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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