Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Compound containing aza-spirofluorene and nitrogen six-membered heterocycle and application of compound to OLED (Organic Light Emitting Diode)

A technology of six-membered heterocycles and organic compounds, which is applied in OLED applications, in the field of compounds containing azaspirofluorene and nitrogen-containing six-membered heterocycles, can solve different problems and achieve difficult aggregation, power efficiency and external quantum Efficiency improvement, good film-forming effect

Active Publication Date: 2017-08-08
JIANGSU SUNERA TECH CO LTD
View PDF3 Cites 27 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

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
  • Compound containing aza-spirofluorene and nitrogen six-membered heterocycle and application of compound to OLED (Organic Light Emitting Diode)
  • Compound containing aza-spirofluorene and nitrogen six-membered heterocycle and application of compound to OLED (Organic Light Emitting Diode)
  • Compound containing aza-spirofluorene and nitrogen six-membered heterocycle and application of compound to OLED (Organic Light Emitting Diode)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The synthesis of embodiment 1 intermediate A:

[0038]

[0039](1) Under a nitrogen atmosphere, weigh raw material B and dissolve it in tetrahydrofuran, then add raw material C and tetrakis(triphenylphosphine)palladium, stir the mixture, then add potassium carbonate aqueous solution, and mix the above-mentioned reactants at the reaction temperature At 70-90°C, heat to reflux for 5-20 hours. After the reaction, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, the obtained residue was purified by silica gel column to obtain intermediate I;

[0040] The molar ratio of raw material B to raw material C is 1:1.0~1.5, the molar ratio of tetrakis(triphenylphosphine) palladium to raw material B is 0.001~0.02:1, and the molar ratio of potassium carbonate to raw material B is 1.0~2.0 :1, the ratio of THF dosage to raw material B is 1g:10~30ml.

[004...

Embodiment 2

[0063] The synthesis of embodiment 2 compound 2:

[0064]

[0065] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol of raw material A1, 150ml of THF, 0.015mol of intermediate A1, 0.0001mol of tetrakis(triphenylphosphine) palladium were added, stirred, and then 0.02mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 15 hours, sampled and plated, 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 compound with a HPLC purity of 99.1% and a yield of 77.3%. Elemental analysis structure (molecular formula C 45 h 28 N 4 ): theoretical value C, 86.51; H, 4.52; N, 8.97; test value: C, 86.49; H, 4.53; N, 8.98. ESI-MS(m / z)(M + ): The theoretical value is 624.23, and the measured value is 624.58.

Embodiment 3

[0066] The synthesis of embodiment 3 compound 4:

[0067]

[0068] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol of raw material A2, 150ml of THF, 0.015mol of intermediate A2, 0.0001mol of tetrakis(triphenylphosphine) palladium were added, stirred, and then 0.02mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 15 hours, sampled and plated, 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 compound with an HPLC purity of 99.3% and a yield of 71.9%. Element analysis structure (molecular formula C 51 h 32 N 4 ): theoretical value C, 87.40; H, 4.60; N, 7.99; test value: C, 87.42; H, 4.61; N, 7.97. ESI-MS(m / z)(M + ): The theoretical value is 700.26, and the measured value is 700.63.

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

PropertyMeasurementUnit
Thicknessaaaaaaaaaa
Thicknessaaaaaaaaaa
Thicknessaaaaaaaaaa
Login to View More

Abstract

The invention discloses a compound containing aza-spirofluorene and nitrogen six-membered heterocycle and application of the compound to an OLED (Organic Light Emitting Diode). The compound contains an aza-spirofluorene structure and an aza-six-membered heterocyclic structure; in addition, at least one N is arranged on the spirofluorene structure; and both two groups are strong electron groups, have deep HOMO energy level and high electron mobility, and are suitably used as a hole-blocking material or an electron transport material. A structure containing a hole group of the compound disclosed by the invention can balance electrons and holes of the material, so that the material can be used as a main body material of a partially-electronic luminescent layer; besides, the compound disclosed by the invention has higher group rigidity and has the characteristics of low possibilities of intermolecular crystallization and aggregation and high film-forming property; the compound serving as an organic electroluminescence functional layer material is applies to an OLED device; current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; and besides, the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing azaspirofluorene and a nitrogen-containing six-membered heterocyclic ring, 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. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitt...

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): C07D221/20C07D401/04C07D401/10C07D401/14C07D403/14C07D405/14C07D413/14C07D471/04C07D471/10H01L51/54C09K11/06
CPCC09K11/06C07D221/20C07D401/04C07D401/10C07D401/14C07D403/14C07D405/14C07D413/14C07D471/04C07D471/10C09K2211/1059C09K2211/1088C09K2211/1029C09K2211/1044H10K85/654H10K85/657H10K85/6574H10K85/6572
Inventor 张兆超李崇吴英杰於哲峰
Owner JIANGSU SUNERA TECH CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com