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Organic compound based on triazine and benzimidazole and application thereof to organic light-emitting diode (OLED) device

An organic compound, benzimidazole technology, applied to the application of organic electroluminescent devices, in the field of organic compounds, can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc., to achieve reduced deformation effects, high density, and improved The effect of stability

Active Publication Date: 2017-07-14
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure is complicated to manufacture, and the process of using a surface covering layer is simple, and the luminous efficiency is increased by more than 30%, which is particularly concerned by people.

Method used

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  • Organic compound based on triazine and benzimidazole and application thereof to organic light-emitting diode (OLED) device
  • Organic compound based on triazine and benzimidazole and application thereof to organic light-emitting diode (OLED) device
  • Organic compound based on triazine and benzimidazole and application thereof to organic light-emitting diode (OLED) device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of Intermediate I

[0048]

[0049] Weigh under nitrogen atmosphere The bromide is dissolved in tetrahydrofuran (THF), then bis(pinacol radical) diboron, (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II) and potassium acetate are added, The mixture is stirred, and the mixed solution of the above reactants is heated to reflux at a reaction temperature of 70-90° C. for 5-10 hours; after the reaction is completed, water is added to cool, and the mixture is filtered and dried in a vacuum oven. The obtained residue was separated and purified by silica gel column to obtain Pinacol borate;

[0050]

[0051] Under a nitrogen atmosphere, weigh the raw material A and dissolve it in N,N-dimethylformamide, namely DMF, and then Add palladium acetate and palladium acetate, stir the mixture, then add potassium phosphate aqueous solution, and heat the mixed solution of the above reactants to reflux at a reaction temperature of 120-150°C for 5-15 hours; afte...

Embodiment 2

[0067] Example 2: Intermediate Synthesis

[0068] When R 2 Or R 3 When expressed as the structure of general formula (2),

[0069]

[0070] (1) In a 250mL three-necked flask, pass nitrogen into it, add 0.02mol of raw material 2-bromo-benzimidazole, 0.03mol I-Ar 4 , 0.04mol sodium hydride, 0.004mol cuprous iodide and 0.01mol o-phenanthroline were dissolved in 100ml 1,3-dimethyl-2-imidazolinone, stirred and reacted for 20-30h. After the reaction, add water and use two Extract with methyl chloride, dry the organic layer with anhydrous sodium sulfate, rinse with a mixture of petroleum ether and ethyl acetate as the eluent, the volume ratio of petroleum ether to ethyl acetate in the eluent is 1:100, and purify by column chromatography , Get intermediate M;

[0071]

[0072] (2) Under nitrogen atmosphere, weigh the intermediate M and dissolve it in tetrahydrofuran, and then dissolve the Br-Ar 2 -B(OH) 2 And tetrakis (triphenylphosphine) palladium, stir the mixture, and then add saturated...

Embodiment 3

[0102] Example 3: Synthesis of Compound 1:

[0103]

[0104] In a 250mL three-necked flask, add nitrogen, add 0.01mol intermediate A1, 150ml DMF, 0.03mol intermediate B1, 0.0002mol palladium acetate, stir, and then add 0.02mol K 3 PO 4 The aqueous solution was heated to 150°C, and the reaction was refluxed for 24 hours. The sample was spotted and the reaction was complete. Naturally cooled, extracted with 200 ml of dichloromethane, separated into layers, the extract was dried with anhydrous sodium sulfate, filtered, the filtrate was rotary evaporated, and purified by silica gel column to obtain the target product with an HPLC purity of 99.2% and a yield of 64.3%.

[0105] Elemental analysis structure (molecular formula C 57 H 37 N 9 ): Theoretical value C, 80.74; H, 4.40; N, 14.87; Test value: C, 80.74; H, 4.41; N, 14.85. ESI-MS(m / z)(M + ): The theoretical value is 847.32, and the measured value is 847.70.

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Abstract

The invention relates to an organic compound based on triazine and benzimidazole and application thereof to an organic light-emitting diode (OLED) device. The compound disclosed by the invention has a high vitrification temperature and high molecular thermal stability; the compound has a low absorption rate and a high refraction rate in the field of visible light, and can be applied to a CPL (Circular-Polarizing Filter) layer of the OLED device to effectively increase the light output efficiency of the OLED device; the compound also has a deep HOMO (Highest Occupied Molecular Orbital) energy level and a high electron mobility, can be taken as a hole-blocking / electron transport layer material of the OLED device, and can effectively block holes or prevent energy from being transported from a light-emitting layer to one side of an electron layer, so that the compound efficiency of the holes and electrons on the light-emitting layer is increased, and the light-emitting efficiency and the service life of the OLED device are increased and prolonged.

Description

Technical field [0001] The present invention relates to the field of semiconductor technology, in particular to an organic compound with triazine and benzimidazole as the core and its application in organic electroluminescence devices. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products as well as new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a broad application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various different functional materials are superimposed on each other according to their uses to form an OLED light-emitting device. The OLED light-emitting device is a current device. When a voltage is applied to the electrodes at its two ends an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D403/10C07D403/14C07D405/14H01L51/54
CPCC07D401/14C07D403/10C07D403/14C07D405/14H10K85/626H10K85/654H10K85/6574H10K85/6572H10K50/00
Inventor 张兆超唐丹丹李崇
Owner JIANGSU SUNERA TECH CO LTD
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