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Aromatic amine compound containing 9, 9'-spirobifluorene and dibenzofuran and organic electroluminescent device thereof

A technology of benzofuran and spirobifluorene, which is applied in the field of organic photoelectric materials, can solve the problems of shortened lifespan, color purity and low efficiency of organic electrical components, and achieve charge balance, hole transport ability and stability improvement, The effect of lowering the driving voltage

Inactive Publication Date: 2018-10-23
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the case of emitting light at the interface of the hole transport layer, the color purity and efficiency of the organic electrical device will be lowered and the lifetime will be shortened.

Method used

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  • Aromatic amine compound containing 9, 9'-spirobifluorene and dibenzofuran and organic electroluminescent device thereof
  • Aromatic amine compound containing 9, 9'-spirobifluorene and dibenzofuran and organic electroluminescent device thereof
  • Aromatic amine compound containing 9, 9'-spirobifluorene and dibenzofuran and organic electroluminescent device thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the preparation of bromide B

[0061]

[0062]

[0063] Preparation of Bromide B-1:

[0064]

[0065] a) Under nitrogen atmosphere, dissolve methyl 2-iodo-3-bromobenzoate (10.0g, 30mmol), phenylboronic acid (3.66g, 30mmol) and tetrakis(triphenylphosphine)palladium (1.7g, 1.46mmol) In 100ml of THF, stirred for 30 minutes, then added dropwise 50ml of potassium carbonate aqueous solution (1.63g, 11.18mmol) within 20 minutes, refluxed overnight, washed with water, extracted with dichloromethane, evaporated the organic solvent; b) the resulting solid (8.5 g, 255.0mmol) and sodium hydroxide (1.2g, 30mmol) were dissolved in 100ml ethanol, refluxed for 6 hours, cooled to room temperature, neutralized with 2M hydrochloric acid, filtered, and the resulting solid was recrystallized in ethanol; c) obtained Crystals (10g, 30mmol) were dissolved in 300ml methanesulfonic acid, stirred at 30°C for 24 hours, poured into ice water, filtered, washed with water, dri...

Embodiment 2

[0071] Embodiment 2: the preparation of bromide C

[0072]

[0073] Preparation of Bromide C-1:

[0074]

[0075] a) 1-bromo-2-methoxynaphthalene (4.74g, 20mmol), pinacol diboronate (6.22g, 24mmol), 1,1'-bis(diphenylphosphine)-ferrocene- Palladium dichloride (II) dichloromethane complex (0.49g, 0.6mmol), potassium acetate (5.90g, 60mmol) and 79ml of toluene were reacted under reflux for 16 hours, cooled, added 26ml of water, stirred for 30 minutes, separated The organic phase was filtered through a short celite bed, and then the organic solvent was evaporated, and the resulting crude product was recrystallized in heptane / toluene; the solid (4.26 g, 15 mmol) obtained in the previous step, 1-bromo-2-fluoro- 3-iodobenzene (4.05g, 14.3mmol), tetrakis(triphenylphosphine)palladium (0.35g, 0.3mmol), toluene (43ml), 2M aqueous sodium carbonate solution (21ml) were added to the flask, and the reaction was refluxed for 8 hours. Cool to room temperature, extract with toluene, was...

Embodiment 3

[0081] Embodiment 3: the preparation of aromatic amine compound A

[0082]

[0083] Preparation of Compound A-1:

[0084]

[0085] Add bromobenzene (4.71g, 30mmol), cuprous iodide (0.06g, 0.3mmol), and 45ml of liquid ammonia into the flask, react at 100°C for 18 hours, filter, the liquid is extracted, washed, dried, and the organic solvent is removed , and finally obtain compound A-1.

[0086] Compounds A-2 to A-31 can all be prepared by the above methods.

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Abstract

The invention provides an aromatic amine compound containing 9, 9'-spirobifluorene and dibenzofuran and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The preparation method of the compound is simple, the raw material is easy to obtain, the aromatic amine compound has the highest occupied molecular orbital energy level, a high T1 value and a high refractive index, has good hole transporting ability, thermal stability and film forming properties, is applied to the OLED device, can significantly improve the luminous efficiency, heat resistance and service life of the device and can effectively reduce the driving voltage of the device.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound containing 9,9'-spirobifluorene and dibenzofuran and an organic electroluminescence device thereof. Background technique [0002] Organic light-emitting diode (Organic Light-Emitting Diode, OLED), also known as organic electro-laser display, is the third-generation display technology after CRT (Cathode Ray Tube, cathode ray tube) and LCD (Liquid Crystal Display, liquid crystal display) , has the advantages of high brightness, high contrast, high definition, wide viewing angle, wide color gamut, ultra-thin, ultra-light, low power consumption, wide temperature, self-illumination, high luminous efficiency, short response time, transparency, and flexibility. The basic structure is like a sandwich structure, which is composed of an indium tin oxide anode, a metal cathode and an organic layer between the two. It is a double-injection l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/77C07D307/91C07D405/12C07D409/12C09K11/06H01L51/54
CPCC09K11/06C07D307/77C07D307/91C07D405/12C07D409/12C09K2211/1029C09K2211/1011C09K2211/1092C09K2211/1088H10K85/625H10K85/624H10K85/636H10K85/633H10K85/6576H10K85/6574H10K85/6572
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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