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Compound containing triazine and carbazole structure and organic electroluminescent device

A compound, carbazole technology, applied in the field of organic electroluminescence, can solve the problems that restrict the development and application of OLED, and achieve the effect of good luminous efficiency and lifespan

Active Publication Date: 2021-10-08
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Total reflection will occur at the interface between the ITO film and the glass substrate and the interface between the glass substrate and the air, and the light emitted to the front of the OLED device to the external space accounts for about 20% of the total EL of the organic material film, and the remaining about 80% of the light Mainly in the form of guided waves, it is limited to organic material thin films, ITO thin films and glass substrates, which seriously restricts the development and application of OLEDs. How to reduce the total reflection effect in OLED devices and increase the proportion of light coupled to the external space before the device , and then improving the performance of the device has attracted widespread attention

Method used

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  • Compound containing triazine and carbazole structure and organic electroluminescent device
  • Compound containing triazine and carbazole structure and organic electroluminescent device
  • Compound containing triazine and carbazole structure and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0148]

[0149] The synthetic method of compound 1 is as follows:

[0150]

[0151] Under nitrogen protection, 1-a (50g, 127mmol, 1eq), 1-b (39.2g, 134mmol, 1.05eq), potassium carbonate (44g, 318mmol, 2.5eq), Pd(PPd3 )4 (2.94g, 2.54mmol, 0.02eq), 400mL of toluene, 200mL of ethanol, and 120mL of water. After the addition, the temperature was raised to 105°C and the reaction was stirred. The reaction progress was monitored by HPLC. When the compound 1-a ≤ 1%, the reaction was stopped. Add 200mL of water, cool down and stir to crystallize. After cooling down to room temperature, suction filter to obtain a filter cake. The filter cake is air-dried at 85°C for 12 hours to obtain 46.3g of gray solid 1-c, ESI-MS (m / z) (M+): theoretical value 409.48, measured value 409.12, elemental analysis results (molecular formula C30H19NO): theoretical value C, 88.00; H, 4.68; N, 3.42; O, 3.91; measured value C, 87.91; H, 4.69; N, 3.50; O, 3.90.

[0152]Under the protection of nitrogen, 1...

Embodiment 2

[0154]

[0155] The synthetic method of compound 2 is as follows:

[0156]

[0157] The preparation method is basically the same as in Example 1, the only difference is that 1-c in Example 1 is replaced by 2-c to obtain the final target product compound 2 with a yield of 46.4%, ESI-MS (m / z) (M+) : theoretical value 645.76, measured value 645.31, elemental analysis results (molecular formula C45H23D5N4O): theoretical value C, 83.70; H, 5.15; N, 8.68; O, 2.48; measured value C, 83.78; H, 5.09; N, 8.57; O , 2.56.

Embodiment 3

[0159]

[0160] The synthetic method of compound 3 is as follows:

[0161]

[0162]

[0163] Under nitrogen protection, in a 2L three-necked flask, 3-a (60g, 244mmol, 1eq), 3-b (42g, 269mmol, 1.1eq), tetrakistriphenylphosphine palladium (4.2g, 3.6mmol, 0.015 eq), potassium carbonate (85g, 615mmol, 2.75eq), 500mL toluene, 125mL ethanol and 125mL water, after the addition, the temperature was raised to 85°C and the reaction was stirred, and the reaction progress was monitored by HPLC. When the compound 3-a ≤ 1%, the reaction was stopped , after the reaction solution was naturally cooled to room temperature, 200mL of water was added, stirred for 10min, filtered with suction, washed with water, rinsed with ethanol, and dried at 85°C for 12 hours to obtain 62.9g of intermediate 3-c with a yield of 93%, ESI- MS (m / z) (M+): theoretical value 277.75, measured value 277.52, elemental analysis results (molecular formula C18H12ClN): theoretical value C, 77.84; H, 4.35; N, 5.04; ...

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Abstract

The invention discloses a compound containing a triazine and carbazole structure and an organic electroluminescent device, and relates to the technical field of organic electroluminescence. According to the invention, carbazole and a carbazole derivative are directly connected with triazine in a single bond mode, and the connection mode has the advantages that the electron withdrawing characteristic of triazine is good, the electron cloud density of carbazole and carbazole derivatives connected with the triazine is directly reduced, so that the chemical stability and the thermal stability of material molecules are further improved, and the luminous efficiency and the service life of a device are further improved. Meanwhile, phenyl or deuterated phenyl is used for protecting part of active positions of dibenzofuran, so that the chemical stability and the thermal stability of the material are improved, the luminous efficiency of a device is improved, and the service life of the device is prolonged.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound containing triazine and carbazole structures and an organic electroluminescence device. Background technique [0002] Organic light-emitting devices (Organic Light-emitting Devices, OLED) are spontaneous light-emitting devices using the following principle: when an electric field is applied, fluorescent substances emit light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and is ultra-thin, and can be fabricated on flexible panels. It is widely used in mobile phones, tablet computers, TVs, lighting, etc. and other fields. [0003] Compared with the crystal layer of LED (light-emitting diode) or LCD (liquid crystal display...

Claims

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Application Information

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IPC IPC(8): C07D405/14C09K11/06H01L51/50H01L51/54
CPCC07D405/14C09K11/06C09K2211/1029C09K2211/1074C09K2211/1088C09K2211/1007H10K85/6574H10K85/6572H10K50/11
Inventor 钱超许军朱东林黄明辉
Owner NANJING TOPTO MATERIALS CO LTD
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