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

A technology of electroluminescent devices and organic compounds, which is applied to organic compounds based on triazine and quinoxaline, and the application field of organic electroluminescent devices, which can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc. Achieve the effect of avoiding free rotation, high density and high Tg temperature

Inactive Publication Date: 2018-01-12
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, an...

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: the synthesis of intermediate I

[0051]

[0052] Under nitrogen atmosphere, weigh 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 pinacol borate;

[0053]

[0054] 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 a reaction temperature of 120-150°C for 5-15 hours; after the reaction ...

Embodiment 2

[0071] Embodiment 2: intermediate Synthesis

[0072] When R 2 or R 3 When expressed as a structure of general formula (2),

[0073]

[0074] (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;

[0075]

[0076] (2) Under a nitrogen atmosphere, weigh the intermediate M and dissolve it in N,N-dimethylformamide (DMF), then add bis(pinacolyl)diboron, (1,1'-bis(dip...

Embodiment 3

[0100] Embodiment 3: the synthesis of compound 1:

[0101]

[0102] In a 250mL three-necked flask, blow nitrogen gas, add 0.01mol of intermediate A1, 150ml of DMF, 0.03mol of intermediate B1, 0.0002mol of palladium acetate, stir, and then add 0.02mol of 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 99.2% and a yield of 64.3%.

[0103] Elemental analysis structure (molecular formula C 59 h 37 N 9 ): theoretical value C, 81.27; H, 4.28; N, 14.46; test value: C, 81.24; H, 4.26; N, 14.45. ESI-MS(m / z)(M + ): The theoretical value is 871.32, and the measured value is 872.01.

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Abstract

The invention relates to an organic compound based on triazine and quinoxaline and application thereof in an OLED (organic light emitting diode) device. The organic compound has the advantages that the glass transition temperature and the molecular thermal stability are higher; the absorbing rate is low and the reflectivity is high in the field of visible lights; after the organic compound is applied to a CPL (capping layer) layer of the OLED device, the light fetching-out efficiency of the OLED device can be effectively improved; the HOMO (highest occupied molecular orbital) energy level is deep, the electron transfer rate is high, the organic compound can be used as the cavity blocking/electron transmission layer material of the OLED device, the transferring of cavity or energy from thelight emitting layer to one side of the electron layer can be effectively blocked, the compounding efficiency of the cavity and the electron in the light emitting layer is improved, the light emittingefficiency 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 based on triazine and quinoxaline and its application in organic electroluminescent devices. 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 p...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D403/14C07D405/14C07D471/04C07D403/10H01L51/54H01L51/50
Inventor 王芳李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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