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Metal complexes comprising condensed heteroaromatic rings

A heteroaromatic ring and aromatic ring technology, applied in the field of new organometallic complexes, can solve the problems of rare emitters

Active Publication Date: 2015-02-04
UDC IRELAND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These illuminants are currently rare and do not meet the above requirements

Method used

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  • Metal complexes comprising condensed heteroaromatic rings
  • Metal complexes comprising condensed heteroaromatic rings
  • Metal complexes comprising condensed heteroaromatic rings

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0214] Synthesis of 2-(Dibenzo[b,d]furan-4-yl)quinoline (dbfqH)

[0215]

[0216] To 2-chloroisoquinoline (1.73g, 10.5mmol) and Pd(PPh 3 ) 4 (403 mg, 0.349 mmol) in 1,2-dimethoxyethane (50 mL), add dibenzofuran-4-ylboronic acid (2.30 g, 10.9 mmol) in degassed ethanol (50 mL) solution, followed by the addition of 2.6M aqueous sodium carbonate (50 mL). The mixture was then heated at reflux for 19 hours under an inert atmosphere. After cooling, ethyl acetate (50 mL) and water (100 mL) were added, and insoluble materials were removed by filtration. The filtrate was worked up with standard aqueous work-up. The solvent was removed and the residue was purified by column chromatography to give a yellow solid. Recrystallization from chloroform / hexane gave the title compound dbfqH (2.62 g, 8.87 mmol) in 84% yield as a white crystalline solid.

Embodiment 2

[0218] Synthetic Ligands L1 to L44

[0219] Similar to the preparation of (dbfqh) according to Example 1, various analogous compounds such as compounds eg L1 to L44 can be prepared using the Suzuki coupling reaction. The general preparation method is as follows:

[0220] To the halogen compound (10.5mmol; educt 2) and Pd(PPh 3 ) 4 (0.35mmol, 1 / 30 equiv) in 1,2-dimethoxyethane (50mL) was added a solution of boric acid (11mmol; educt 1) in degassed ethanol (50mL), followed by 2.6M aqueous sodium carbonate solution (50 mL). Then, the mixture was heated at reflux for 20 hours under an inert atmosphere. After cooling, ethyl acetate (50 mL) and water (100 mL) were added, and insoluble materials were removed by filtration. The filtrate was worked up with standard aqueous work-up. The solvent was removed and the residue was purified by column chromatography. Recrystallization from chloroform / hexane afforded the compound as a white crystalline solid in about 65 to 90% yield.

...

Embodiment 3

[0231] Synthesis of 2-(3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridine (fppzH) and 2-(3-(perfluorobutyl)-1H-pyrazol-5-yl)pyridine ( hppzH)

[0232]

[0233] The concentrations used in the reactions are provided for both fppzH and hppzH in the description below.

[0234] NaOEt (in case of fppzH: 1.82 g, 26.8 mmol; in case of hppzH: 1.23 g, 18.0 mmol) was dispersed in 50 mL of dry tetrahydrofuran (THF). To this solution was slowly added ethyl trifluoroacetate (3.2 mL, 26.8 mmol) for fppzH or ethyl nonafluoropentanoate (3.0 mL, 15.1 mmol) for hppzH at 0 °C . The mixture was stirred at 0° C. for 2 hours, followed by the addition of 2-acetylpyridine (in case of fppzH: 2.0 mL, 17.9 mmol; in case of hppzH: 1.87 mL, 16.7 mmol). The reaction was then heated to 50 °C for 4 hours. Removal of the solvent gave a brown oily residue which was dispersed in deionized water (50 mL). with 2N HCl (水 溶液) The mixture was neutralized (pH = 4), followed by extraction with ethyl acetate (3 x 50 m...

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Abstract

The present invention relates inter alia to a new class of heteroleptic metal complexes comprising condensed aromatic heterocyclic rings, their preparation and use.

Description

technical field [0001] The present invention relates to novel organometallic complexes, formulations and compositions comprising them, their use in electronic devices and their preparation. Background technique [0002] The structure of organic electroluminescent devices (OLEDs) in which organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. Luminescent materials used for this purpose are increasingly usually organometallic complexes which exhibit phosphorescence rather than fluorescence (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6). For quantum-mechanical reasons, it is possible to achieve up to a four-fold increase in energy and power efficiency using organometallic compounds as phosphorescent emitters. According to the prior art, triplet emitters in phosphorescent OLEDs are in particular iridium and platinum complexes, which are usually cyclometallated. Currently available illumina...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/00A61N5/06C07F15/00C09K11/06H01L51/50H10K99/00
CPCH05B33/10C09K2211/1011A61N5/0616C09K2211/1029C09K2211/1092A61N2005/0663C09K2211/185C07F15/0033H01L51/0085C09K2211/1007C09K11/06A61N5/062C09K2211/1088C09K2211/1059C09K2211/1044A61N2005/0653H01L51/5016Y02E10/549H10K85/342H10K50/11H10K2101/10Y02P70/50C07F15/00A61N5/06Y02E10/542H10K50/00A61N2005/065
Inventor 苏珊·霍伊恩尼尔斯·克嫩杨承翰路伊萨·德科拉
Owner UDC IRELAND
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