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

A technology of dibenzothiophene and spirobifluorene, which is applied in the field of organic photoelectric materials, can solve the problems of low color purity, low efficiency, and short life of organic electrical components, and achieve good hole transport ability, stability, and excellent performance , Improve the effect of luminous efficiency

Inactive Publication Date: 2018-10-16
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 dibenzothiophene and organic electroluminescent device thereof
  • Aromatic amine compound containing 9,9'-spirobifluorene and dibenzothiophene and organic electroluminescent device thereof
  • Aromatic amine compound containing 9,9'-spirobifluorene and dibenzothiophene and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: the preparation of bromide B

[0060]

[0061]

[0062] The preparation of bromide B-1:

[0063]

[0064] 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,...

Embodiment 2

[0070] Embodiment 2: the preparation of aromatic amine compound A

[0071]

[0072]

[0073] Preparation of Compound A-1:

[0074]

[0075] 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.

[0076] Compounds A-2 to A-36 can all be prepared by the above methods.

Embodiment 3

[0077] Embodiment 3: the preparation of intermediate M

[0078]

[0079]

[0080]

[0081] Preparation of intermediate M-1: under argon atmosphere, bromide B-1 (5.93g, 15mmol), aromatic amine compound A-1 (1.40g, 15mmol), sodium tert-butoxide (2.88g, 30mmol) were added to In 150ml of dehydrated toluene, add palladium acetate (0.07g, 0.3mmol) and tri-tert-butylphosphine (0.06g, 0.3mmol) under stirring, and react at 80°C for 8 hours. After cooling, it was filtered through a diatomaceous earth / silica gel funnel, and the filtrate was distilled under reduced pressure to remove the organic solvent. The resulting residue was recrystallized in toluene, and the obtained solid was collected by filtration and dried to obtain intermediate M-1.

[0082] Intermediates M-2 to M-124 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 dibenzothiophene and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The compound has a simple preparation method, easily available raw materials, good hole transport capability and stability, can realize charge balance in a light-emitting layer, has a suitable highest occupied molecular orbital energy level, a high T1 value and a high refractive index, can remarkably improve the light emitting efficiency, the heat resistance and the servicelife of the device when applied to an OLED device, and can also effectively reduce the driving voltage of the device, thereby being an OLED material with excellent performance.

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 dibenzothiophene and an organic electroluminescence device thereof. Background technique [0002] Organic Light-Emitting Diode (OLED) is the third-generation display technology after CRT (Cathode Ray Tube, cathode ray tube) and LCD (Liquid Crystal Display, liquid crystal display), with high brightness, high contrast, high-definition High degree, wide viewing angle, wide color gamut, low power consumption, wide temperature, high luminous efficiency, short reaction time, transparency, flexibility, etc. The basic structure is composed of an indium tin oxide anode, a metal cathode and an organic layer between the two , is a double-injection light-emitting device, which directly converts electrical energy into light energy of organic semiconductor material molecules. It uses the physical mechanism o...

Claims

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Application Information

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IPC IPC(8): C07D333/50C07D409/12C07D333/76C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D333/50C07D333/76C07D409/12C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1022C09K2211/1014C09K2211/1011C09K2211/1007H10K85/624H10K85/636H10K85/626H10K85/633H10K85/631H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K50/15H10K50/11
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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