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Transition metal complex compound and organic electroluminescent device using same

A technology of coordination compounds and transition metals, applied in luminescent materials, organic chemistry, and compounds containing elements of Group 8/9/10/18 of the periodic table, etc., can solve energy efficiency, low external quantum efficiency, no inspiration, There is no mention of issues such as long-life luminescence

Inactive Publication Date: 2008-08-27
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the energy efficiency and external quantum efficiency are low, and there is no mention of a long life of the luminescent life.
[0013] On the other hand, in Patent Documents 21 and 22, as tris(2-phenylpyridine-N,C 2 ) The long-lived method of iridium coordination compound discloses to make 3 2-phenylpyridine-N, C 2 The method of cross-linking the base part, but only discloses a variety with a benzene ring skeleton in the 3-leg type cross-linking part, which cannot significantly increase the lifespan. In addition, it does not suggest that it can be used for cyan light emission.

Method used

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  • Transition metal complex compound and organic electroluminescent device using same
  • Transition metal complex compound and organic electroluminescent device using same
  • Transition metal complex compound and organic electroluminescent device using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0334] Embodiment 1 (synthesis of transition metal coordination compound 1)

[0335] (i) Synthesis of cross-linked ligand precursor (compound a)

[0336] The crosslinking ligand precursor (compound a) was synthesized by the following reaction procedure.

[0337] [chem 44]

[0338]

[0339] Add 100ml tetrahydrofuran (THF) to 5.00g N-phenylimidazole (molecular weight 144.18, 34.7 mmol) and 5.05 g of 1,4-diiodobutane (molecular weight 309.92, 16.3 mmol), stir at room temperature for 8 Hour. The resulting white solid (compound a) was filtered off, and the filtrate was stirred for 8 hours (this operation was repeated twice) to obtain a total of 5.50 g of compound a (yield 56%).

[0340] (ii) Synthesis of ligand precursor (compound b)

[0341] The ligand precursor (compound b) was synthesized by the following reaction procedure.

[0342] [chem 45]

[0343]

[0344] To 9.21 g of N-phenylo-phenylenediamine (molecular weight 184.24, 50 mmol) was added 100 ml of toluene, fol...

Embodiment 2

[0416] Embodiment 2 (synthesis of transition metal coordination compound 2)

[0417] (i) Synthesis of the crosslinking group site (compound e)

[0418] Synthesize 1.25 g of the following compound e ( Molecular weight 336.89, 3.71 mmol).

[0419] [Chemical 52]

[0420]

[0421] (ii) Synthesis of ligand (compound f)

[0422] The ligand (compound f) was synthesized by the following reaction procedure.

[0423] [Chemical 53]

[0424]

[0425] 40 ml of tetrahydrofuran was added to 1.93 g of N-phenylimidazole (molecular weight 144.18, 13.4 mmol) and 1.25 g of compound e (molecular weight 336.89, 3.71 mmol), and refluxed for 8 hours. The resulting white solid was filtered off to obtain 1.19 g of compound f (molecular weight 769.41, 1.54 mmol, yield 32%).

[0426] (ii) Synthesis of transition metal complex 2

[0427] Transition metal complex 2 was synthesized by the following reaction procedure.

[0428] [Chemical 54]

[0429]

[0430] The entire reaction was carried...

Embodiment 3

[0432] Embodiment 3 (synthesis of transition metal coordination compound 3)

[0433] The transition metal complex 3 was synthesized by the following reaction procedure.

[0434] [Chemical 55]

[0435]

[0436] The entire reaction was carried out under argon flow. 21 ml of 2-ethoxyethanol was added as a solvent to 0.140 g of compound c (molecular weight 671.70, 0.209 mmol), followed by 0.142 g of sodium ethoxide (molecular weight 68.05, 2.09 mmol), and stirred at room temperature for 1 hour. 0.157 g of compound g (molecular weight 376.19, 0.418 mmol) was added thereto, followed by 0.250 g of compound a (molecular weight of 598.26, 0.418 mmol), and the reaction was carried out under reflux for 2 hours. From the obtained reaction solution, 2-ethoxyethanol as a solvent was distilled off by heating under reduced pressure, and the obtained solid was purified by silica gel column chromatography (developing solvent: dichloromethane, Rf value about 0.8). As a result, 0.013 g of c...

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Abstract

Disclosed is a transition metal complex compound having a specific structure including a crosslinked stricture. Also disclosed is an organic electroluminescent device wherein an organic thin film, which is composed of one or more layers including at least a light-emitting layer, is sandwiched between a pair of electrodes. In this organic electroluminescent device, at least one layer of the organic thin film contains the transition metal complex compound.

Description

technical field [0001] The present invention relates to a transition metal coordination compound and an organic electroluminescent element using the compound, in particular to an organic electroluminescent element with high luminous efficiency and cyan light emission and a novel transition metal for realizing the organic electroluminescent element coordination compound. Background technique [0002] An organic electroluminescent element (EL) is a self-luminous element utilizing the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. C.W.Tang et al. from Eastman Kodak reported low-voltage drive organic EL elements based on stacked elements (C.W.Tang, S.A.Vanslyke, Applied Physics Letters, Vol. 51, Page 913, 1987, etc.) Since then, research on organic EL elements using organic materials as constituent materials is constantly on the rise. Tang et al. use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07D233/58C07D235/04C09K11/06H01L51/50
Inventor 渡边正美松浦正英长岛英明
Owner IDEMITSU KOSAN CO LTD
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