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Oled device employing alkali metal cluster compounds

A compound and alkali metal salt technology, applied in the field of alkali metal cluster compounds, can solve problems such as performance limitations, and achieve the effects of improving efficiency, reducing device driving voltage, and improving working stability

Active Publication Date: 2010-11-03
GLOBAL OLED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although organic electroluminescent (EL) devices have been known for more than 20 years, their performance limitations have been an obstacle to many desired applications

Method used

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  • Oled device employing alkali metal cluster compounds
  • Oled device employing alkali metal cluster compounds
  • Oled device employing alkali metal cluster compounds

Examples

Experimental program
Comparison scheme
Effect test

experiment example

[0423] In process figure 1 The synthesis of 2-(1,10-phenanthrolin-2-yl)-phenol lithium (5), the raw material required for the preparation of Inv-1, is outlined in a diagram.

[0424] plan 1

[0425]

[0426]

[0427] 2-Chloro-1,10-phenanthroline (1):

[0428] 2-Chloro-1,10-phenanthroline was prepared from 1,10-phenanthroline according to the steps of BEHalcrow, Wm.O.Kermack, Journal of the Chemical Society (1946), 155-7, and satisfactorily The yield is isolated.

[0429] 2-(2-Methoxyphenyl)-1,10-phenanthroline hydrochloride (3):

[0430] Combine 2-chloro-1,10-phenanthroline (5.9g, 27.5mMole), 2-methoxyphenylboronic acid (2) (5g, 33mMole), tetrakis(triphenylphosphine)palladium (0)( 1g, 0.825mMole), 2M-Na 2 CO 3 (33mL, 66mMole) and ethanol (8mL) were suspended in toluene (70mL), heated to 100°C and fully stirred for 24 hours. At the end of this time, the reaction was cooled, diluted with ethyl acetate (200 mL), and the aqueous layer was removed. The organic layer was washed with water...

Embodiment 1

[0435] Example 1 (Route A)-Synthesis of compound Inv-1 of the present invention in solvent:

[0436]

[0437] Lithium quinolate (6) (3g, 19.86mMole) and 2-(1,10-phenanthrolin-2-yl)-lithium phenoxide (5) (2.76g, 9.92mMole) in o-dichlorobenzene ( The mixture in 50 mL) was slowly refluxed for 45 minutes. The pale yellow solution was cooled and crystallization was induced by scraping the walls of the flask. The Inv-1 crystals were filtered out, washed thoroughly with ether and dried. The yield of the product Inv-1 was 4.0 g. Before being used to manufacture devices, the Inv-1 is heated at 290℃ / 10 -3 mm Hg sublimation.

[0438] Example 1 (Route B):-Alternative synthesis of the compound of the present invention Inv-1 by direct sublimation:

[0439] Combine lithium quinolate (5) (1.5g, 9.93mMole) and 2-(1,10-phenanthrolin-2-yl)-phenol lithium (6) (1.4g, 4.96) in a mortar with a pestle. mMole) ground into a dense mixture. Then at 290℃ / 10 -3 mm Hg sublimed the material mixture to obtain...

Embodiment 2

[0440] Example 2 (Route B):-Synthesis of the compound of the invention Inv-5 by direct sublimation:

[0441] Grind lithium pentafluorophenolate (1g, 1.32mMole) and 2-(1,10-phenanthrolin-2-yl)-lithium phenolate (6) (0.37g, 0.66mMole) in a mortar with a pestle. Dense mixture. Then at 235℃ / 10 -3 mm Hg sublimed the material mixture to obtain 0.2 g of Inv-5.

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Abstract

The invention provides an OLED device containing certain alkali metal cluster compounds with mixed ligands, such compounds, and methods of making them. In particular, the cluster compound is a neutrally charged mixed cluster compound comprising first and second subunits with the first subunit comprising an alkali metal salt of a nitrogen containing a heterocyclic ligand bearing a anionic hydroxy group and the second subunit consisting of an organic alkali metal salt different than the first subunit.

Description

Technical field [0001] The present invention relates to novel and novel alkali metal cluster compounds with mixed ligands and their application in organic light emitting diode (OLED) electroluminescence (EL) devices. Background technique [0002] It is well known that alkali metal salts of aromatic phenols such as lithium and sodium can form discrete cluster compounds, in which multiple alkali metal atoms are coordinated in an orderly manner by multiple ligands. For example, see "Lithium Chemistry: A Theoretical and Experimental Overview", edited by AM. Sapse and P. Von Rague Schleyer, J. Wiley & Sons, NY, 1995, Chapters 7-9 and Kissling et al., J. Org. Chem, 66(26), 9006 (2001). [0003] The cluster compound is stable, the total charge is neutral, and can be formed spontaneously and reproducibly from the mixture. The number of the alkali metal atoms and ligands present in the cluster compound may vary according to the nature of the ligand. In the case of lithium, examples of clu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/54
CPCC09K11/06H01L51/5092H01L51/009H01L51/0077C07D215/30C07D215/14C07D221/16C07D233/64C07D235/18C07D471/04C07D207/333C07D277/66C07D213/30C07C39/44C09B19/02C09B23/105C09B23/148C09B48/00C09B57/00C09B57/008C09B57/02C09B57/10C09B1/00C09B3/14H10K85/30H10K85/361H10K50/171
Inventor 威廉·詹姆斯·贝格利曼尤·拉杰斯瓦兰图卡拉姆·姬珊·哈特瓦尔娜塔莎·安德里夫斯基
Owner GLOBAL OLED TECH
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