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Heterocyclic compound, synthetic method thereof and organic light-emitting diode containing compound

A technology of heterocyclic compounds and synthesis methods, which is applied in the field of organic electroluminescent elements, can solve problems affecting the application of OLED devices, accelerate device attenuation, and reduce device efficiency, so as to increase charge transfer efficiency, prevent crystallization, and operate at low voltage. Effect

Active Publication Date: 2019-09-27
SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In traditional double-layer or multilayer structure devices, the existing hole-transporting material N,N'-di-(1-naphthyl)-N,N'-diphenyl-1,1-biphenyl- The hole transport ability of 4,4-diamine (NPB) is 10-1000 times stronger than the electron transport ability, which will lead to a decrease in the efficiency and lifetime of the device
On the other hand, currently commonly used hole transport materials usually have poor thermal stability, such as N,N'-bis-(1-naphthyl)-N,N'-diphenyl-1,1-biphenyl The glass transition temperature Tg of -4,4-diamine (NPB) is 96°C. The above-mentioned unfavorable factors will accelerate the attenuation of the device and shorten the service life, thus affecting the application of OLED devices in the industry.

Method used

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  • Heterocyclic compound, synthetic method thereof and organic light-emitting diode containing compound
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  • Heterocyclic compound, synthetic method thereof and organic light-emitting diode containing compound

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preparation example Construction

[0050] Synthetic method of the present invention comprises the steps:

[0051] (1) Dissolve raw material Ia and raw material Ib in toluene / ethanol mixed solution (V ethanol: V toluene=20%-40%), add a certain amount of potassium carbonate, tetrabutylammonium bromide, tetratriphenyl Phosphine palladium, the reaction temperature is 50-100°C, the reaction time is 1-10 hours, follow the reaction of the raw materials, add 5-6 times (ml / mmol) of the theoretical amount of raw material Ia toluene for extraction, wash with water until neutral, and dry it in Distill under reduced pressure (pressure -0.08~-0.06MPa) at 30°C~60°C to concentrate to a small amount of solvent and recrystallize to obtain the first step product;

[0052]

[0053] (2) Dissolving the intermediate I in dichloroethane, adding a certain amount of cesium carbonate, the reaction temperature is 40°C-90°C, and the reaction time is 2-8 hours. The reaction solution was extracted with dichloroethane, washed with water u...

Embodiment 1

[0066] Embodiment 1: Compound 1 and its synthetic method

[0067] The structure of compound 1 is as follows:

[0068]

[0069] The synthetic method of above-mentioned compound 1, comprises the steps:

[0070] (1) Dissolve 10mmol of raw material 1a and 10mmol of raw material 1b in 50ml of toluene / ethanol mixed solution (V ethanol:V toluene=20%), under stirring, add 20mmol of potassium carbonate, 0.5mmol of tetrabutylammonium bromide, 0.02mmol of tetra Triphenylphosphine palladium, the reaction temperature is 50 DEG C, and the reaction time is 1 hour. After the reaction of the raw materials is completed, 50 ml of toluene is added for extraction, 100 ml of water is washed to neutrality, and after 10 g of anhydrous sodium sulfate is dried for 30 min, it is distilled under reduced pressure at 45 DEG C ( Pressure -0.06~-0.08MPa) concentrated to a small amount of solvent remaining and then recrystallized to obtain intermediate 11, the reaction equation is as follows:

[0071] ...

Embodiment 2

[0079] Embodiment 2: Compound 2 and its synthetic method

[0080] The structure of compound 2 is as follows:

[0081]

[0082] The synthetic method of above-mentioned compound 2, comprises the steps:

[0083] (1) Dissolve 10mmol of raw material 2a and 10mmol of raw material 2b in 70ml of toluene / ethanol mixed solution (V ethanol:V toluene=30%), under stirring, add 20mmol of potassium carbonate, 1mmol of tetrabutylammonium bromide, 0.02mmol of tetrathree Phenylphosphine palladium, the reaction temperature is 80°C, the reaction time is 3 hours, follow the reaction of the raw materials, add 50ml of toluene to extract, wash with 100ml of water until neutral, dry 30min with 10g of anhydrous sodium sulfate, and distill under reduced pressure at 45°C (pressure -0.06~-0.08MPa) concentrated to the remaining small amount of solvent and recrystallized to obtain intermediate 21, the reaction equation is as follows:

[0084]

[0085] (2) Dissolve 10 mmol of intermediate 21 in 50 ml...

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Abstract

The invention relates to a heterocyclic compound, a synthetic method thereof and an organic light-emitting diode containing the compound. The structural formula of the heterocyclic compound is as shown in the figure I in the specification. According to the heterocyclic compound, the disubstituted pyridino-heterocyclic compound is obtained by introducing oxygen and a sulfur heterocyclic ring such as benzofuran and benzothiophene into a material, the HOMO energy level of the material is improved by the plane structures, the charge transfer efficiency is improved, and the thermodynamic stability of the material is improved; and meanwhile, the triplet-state energy level accords with the exciton binding requirement by virtue of special ortho-substitution connection, and the heterocyclic compound is applied to the organic light-emitting diode, so that the organic light-emitting diode (OLED) has the advantages of being high in efficiency, low in operating voltage and long in service life.

Description

technical field [0001] The invention relates to the field of photoelectric conversion materials and devices, in particular to a heterocyclic compound, a synthesis method thereof and an organic electroluminescent element containing the compound. Background technique [0002] An organic light emitting diode (OLED) is a self-emitting device, has advantages such as a wide viewing angle, excellent contrast, fast response, high brightness, and excellent driving voltage characteristics, and can provide color images. [0003] Such organic light emitting devices can be roughly classified into inorganic light emitting devices and organic light emitting devices. [0004] A general OLED has a structure including a substrate and an anode, a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and a cathode sequentially stacked on the substrate. In this regard, HTL, EML, and ETL are organic thin films formed of organic compounds. [0005] Heterocyclic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07F7/08C09K11/06H01L51/54
CPCC07D491/048C07D495/04C07F7/0814C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1059C09K2211/1044C09K2211/1011C09K2211/1007H10K85/624H10K85/615H10K85/657
Inventor 王亚龙李红燕唐聪薛震王金平陈志伟杨凯凯赵宇
Owner SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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