Unlock instant, AI-driven research and patent intelligence for your innovation.

Aromatic amine compound containing phenanthroline and organic electroluminescent device thereof

An o-phenanthroline and aromatic amine technology, applied in the field of organic optoelectronic materials, can solve problems such as poor hole mobility, and achieve the effects of improving luminous efficiency, reducing driving voltage and excellent performance.

Inactive Publication Date: 2018-10-16
CHANGCHUN HYPERIONS TECH CO LTD
View PDF13 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the compounds used as the hole transport layer are mostly arylamine compounds containing fluorene, carbazole, dibenzofuran, dibenzothiophene, other aryl or heteroaryl groups, but the hole mobility of these compounds is insufficient. Good, requires development of compounds with higher hole mobility

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Aromatic amine compound containing phenanthroline and organic electroluminescent device thereof
  • Aromatic amine compound containing phenanthroline and organic electroluminescent device thereof
  • Aromatic amine compound containing phenanthroline and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the preparation of intermediate A

[0062] 12.96g (50mmol) 4-bromo-1,10-phenanthroline (Y1), 15.24g (60mmol) biboronic acid pinacol ester, 1.10g (1.5mmol) [1,1'-bis(diphenyl Phosphino) ferrocene] palladium dichloride and 14.72g

[0063] (150mmol) Potassium acetate was dissolved in 328ml of toluene, under an argon atmosphere, refluxed for 12 hours, cooled to room temperature, passed through a diatomaceous earth funnel, removed the solvent, and the residue was recrystallized in heptane to obtain intermediate A

[0064] (13.17 g, 43 mmol).

Embodiment 2

[0065] Embodiment 2: the preparation of intermediate M

[0066]

[0067] Preparation of intermediate M-1: 12.25g (40mmol) intermediate A, 11.33g (40mmol) p-bromoiodobenzene, 0.62g (0.53mmol) tetrakis (triphenylphosphine) palladium, 115ml toluene and 56ml aqueous sodium carbonate (2M) was dropped into a flask, refluxed for 8 hours, cooled to room temperature, extracted with toluene, the organic phase was washed with saturated brine, dried, and purified by column chromatography to finally obtain intermediate M-1 (10.59g, 31.6mmol ).

[0068] Intermediate M-2 to intermediate M-7 can all be prepared by the above methods.

Embodiment 3

[0069] Embodiment 3: the preparation of compound HT1

[0070]

[0071] Under an argon atmosphere, dissolve 10.06g (30mmol) of intermediate M-1, 5.08g (30mmol) of diphenylamine, and 5.77g (60mmol) of sodium tert-butoxide in 300ml of dehydrated toluene, and add 0.13g (0.6mmol) of acetic acid under stirring Palladium and 0.16 g (0.6 mmol) of triphenylphosphine were reacted 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 dried to obtain 11.44 g (27 mmol) of compound HT1 with a yield of 90%. Mass Spectrum m / z: 423.89 (calculated: 423.52). Theoretical element content (%)C 30 h 21 N 3 : C, 85.08; H, 5.00; N, 9.92. Measured element content (%): C, 85.06; H, 5.02; N, 9.88. The above results confirmed that the obtained product was the target product.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides an aromatic amine compound containing phenanthroline and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. Thecompound has a simple preparation method, easily available raw materials, good thermal stability and chemical stability, high hole mobility, good stability and film-forming property, as well as a suitable highest occupied molecular orbital energy level, a high T1 value and a high refractive index, can be applied to an OLED device as a light-emitting auxiliary layer and a hole transport layer, andcan realize charge balance in a light-emitting layer, thereby remarkably improving the light-emitting efficiency, the heat resistance and the service life of the device, simultaneously reducing the driving voltage of the device, and 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 o-phenanthroline and an organic electroluminescence device thereof. Background technique [0002] Typically, an organic electroluminescence (OLED) device is composed of an anode, a cathode, and one or more organic thin film layers between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side into the light-emitting region, holes are injected into the light-emitting region from the anode side, and the two recombine in the light-emitting region to become an excited state, and emit light when the excited state returns to the ground state. Therefore, it is important to develop a compound that efficiently transports electrons or holes to the light-emitting region and facilitates recombination of electrons and holes to obtain a high-efficiency OLED device. ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D471/04C09K11/06C07B59/00H01L51/50H01L51/54
CPCC09K11/06C07B59/002C07D471/04C07B2200/05C09K2211/1092C09K2211/1088C09K2211/1014C09K2211/1011C09K2211/1007C09K2211/1029H10K85/624H10K85/636H10K85/626H10K85/633H10K85/631H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/15H10K50/11
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD