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Organic compound based on pyridine and quinoxaline and application of organic compound to OLED (organic light emission diode) device

An organic compound, azabenzene technology, applied in the field of organic compounds and its application in OLED, can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc.

Inactive Publication Date: 2018-01-19
VALIANT 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, but the process of using the surface covering layer is simple, and the luminous efficiency can be increased by more than 30%, which is particularly concerned by people.

Method used

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  • Organic compound based on pyridine and quinoxaline and application of organic compound to OLED (organic light emission diode) device
  • Organic compound based on pyridine and quinoxaline and application of organic compound to OLED (organic light emission diode) device
  • Organic compound based on pyridine and quinoxaline and application of organic compound to OLED (organic light emission diode) device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1: the synthesis of intermediate I

[0074] When azabenzene and Ar 1 When connected by C-C bond,

[0075]

[0076] Under nitrogen atmosphere, weigh Ar 1 The bromide was dissolved in tetrahydrofuran (THF), and then bis(pinacolyl)diboron, (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and potassium acetate were 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 Ar 1 pinacol borate;

[0077]

[0078] Under a nitrogen atmosphere, weigh raw material A and dissolve it in N,N-dimethylformamide (DMF), and then and palladium acetate, stir the mixture, then add aqueous potassium phosphate solution, heat the mixed solution of the above reactants to reflux at...

Embodiment 2

[0100] Embodiment 2: intermediate or Synthesis

[0101] When R 1 or R 2 When expressed as a structure of general formula (6),

[0102]

[0103] (1) Under a nitrogen atmosphere, weigh 2,3-dibromoquinoxaline and dissolve it in tetrahydrofuran, and then Ar 4 -B(OH) 2 And tetrakis (triphenylphosphine) palladium is added, the mixture is stirred, and then saturated potassium carbonate aqueous solution is added, and the mixed solution of the above reactants is heated and refluxed at a reaction temperature of 70-90°C for 10-20 hours; after the reaction is completed, cool and mix The liquid was extracted with dichloromethane, the extract was dried with anhydrous sodium sulfate, and concentrated under reduced pressure, and the concentrated solid was purified by silica gel column to obtain compound intermediate M;

[0104]

[0105] (2) Under a nitrogen atmosphere, weigh the intermediate M and dissolve it in N,N-dimethylformamide (DMF), then add bis(pinacolyl)diboron, (1,1'-...

Embodiment 3

[0131] Embodiment 3: the synthesis of compound 3:

[0132]

[0133] In a 250mL three-neck flask, blow 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, refluxed for 24 hours, sampled and plated, and the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target product with a HPLC purity of 99.4% and a yield of 64.7%.

[0134] Elemental analysis structure (molecular formula C 57 h 37 N 5 ): theoretical value C, 86.45; H, 4.71; N, 8.84; test value: C, 86.46; H, 4.75; N, 8.90. ESI-MS(m / z)(M + ): The theoretical value is 791.30, and the measured value is 791.96.

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Abstract

The invention relates to an organic compound based on pyridine and quinoxaline and an application of the organic compound to an OLED (organic light emission diode) device. The compound has higher glass transition temperature and molecular heat stability, and is low in absorption and high in refractive index in the field of visible light, and light extraction efficiency of the OLED device can be effectively improved after the organic compound is applied to a CPL layer of the OLED device; the compound further has high HOMO energy level and high electron mobility and can be taken as a hole-blocking / electron transfer layer of the OLED device and can effectively prevent holes or energy from being transferred to one side of the electron layer from a luminous layer, so that composite efficiency of the holes and electrons in the luminous layer is improved, the luminous efficiency of the OLED device is improved, and the service life of the OLED device is prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with azabenzene and quinoxaline as its core and its application in OLEDs. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide 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 functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive and negativ...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D401/10C07D405/14C07D405/10C07D403/14C07D403/10C07D471/04C07D519/00C09K11/06H01L51/50H01L51/54
Inventor 王芳张兆超李崇张小庆
Owner VALIANT CO LTD
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