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organic electroluminescent element

An electroluminescent element and electroluminescent technology, applied in electroluminescent light sources, electrical components, electrical light sources, etc., can solve the problems of resource exhaustion and high price

Inactive Publication Date: 2011-12-21
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In particular, iridium exists as a resource in the earth's crust in a very small amount, so there is a possibility of resource depletion, so the price is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0174]

[0175] Under an argon atmosphere, copper(I) chloride (500 mg, 5.1 mmol) was added to 2,6-lutidine (5 mL), and heated and stirred at 100° C. to obtain a homogeneous solution. The solution was left to cool to room temperature, as a result, colorless crystals precipitated. The crystals were separated by filtration, washed with acetone, and then vacuum-dried at 50° C. for 5 hours to obtain a metal complex ((Cu + ) 1 (2,6-Lutidine) 1 (Cl - ) 1 ) (702 mg, 68% yield).

[0176] Elemental analysis Found (%) C: 40.69, H: 4.30, N: 6.89, Cl: 16.50, Calcd for C 7 h 9 NCuCl (%) C: 40.78, H: 4.40, N: 6.79, Cl: 17.20

[0177] The luminescence peak wavelength (excitation lifetime) of the powder sample is 446nm (4.7μs).

[0178]

[0179] On a glass substrate on which a 150 nm-thick ITO film was formed by sputtering, a solution of poly(ethylenedioxythiophene) / polystyrenesulfonic acid (Bayer, trade name: Baytron P) was used to form a 65 nm thick film by spin coating. Thick f...

Embodiment 2

[0185]

[0186] The synthesis of poly(4-vinyl-2,6-lutidine) was carried out according to the following scheme.

[0187]

[0188] In a 4-neck flask with a capacity of 500 mL replaced with nitrogen, 4-bromo-2,6-lutidine (FOCUS company, 9.80 g, 52.7 mmol), Pd(PPh 3 ) 4 (6.09g, 5.27mmol), dehydrated toluene (260mL), nitrogen bubbling for 15 minutes, tributylvinyltin (20.04g, 63.21mmol) was added, and the temperature was raised to reflux temperature (105-107°C). Under a nitrogen atmosphere, after keeping warm for 17 hours, it was cooled and concentrated by an evaporator to obtain 30.29 g of a black liquid.

[0189] Petroleum ether (100 mL) was added to the obtained liquid, and after filtration with celite, the solvent was evaporated. The residue was purified by silica gel column chromatography (developing solvent: hexane: ethyl acetate = 3:1) to obtain 3.0 g (43%) of 4-vinyl-2,6-lutidine.

[0190] 1 H NMR (400MHz, CDCl 3 ): δ6.95(s, 2H), 6.60(m, 1H), 5.92(d, J=17.6Hz, 1H)...

Embodiment 3

[0207]

[0208] Under argon atmosphere, copper(I) iodide (400mg, 2.1mmol) and 1,2,4,5-tetramethylimidazole (1g, 8.1mmol) were heated in dehydrated acetone (10mL) at 50°C Stir and make a homogeneous solution. The solution was left to cool to room temperature, and colorless crystals precipitated out. The crystals were separated by filtration, washed with acetone, and then vacuum-dried at 50° C. for 5 hours to obtain a metal complex ((Cu + ) 1 (1,2,4,5-Tetramethylimidazole) 2(I - ) 1 ) (674 mg, 73% yield).

[0209] Elemental analysis Found (%) C: 38.54, H: 5.44, N: 12.84, I: 28.17, Cu: 13.3, Calcd for C 14 h 12 N 2 CuI(%)C: 38.32, H: 5.51, N: 12.77, I: 28.92, Cu: 14.5

[0210] The luminescence peak wavelength of the powder sample is 425nm.

[0211]

[0212] An organic electroluminescent element was produced in the same manner as in the production example of the organic electroluminescent element of Example 1, and electroluminescence was obtained by applying a voltage...

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Abstract

The present invention provides an organic electroluminescence element, which sandwiches an organic layer containing a metal coordination compound represented by the following formula (1) between a pair of electrodes composed of an anode and a cathode, in the MLaXb (1) formula, M is a metal ion of Group 11 of the periodic table, L is a ligand represented by the following formula (2), X is an anion, and a and b are as defined in the description; in the formula, A is from the following formula (3) or Formula (4) is a divalent group after removing 2 hydrogen atoms, D1, k1, m1, A, D1, Q1 and Q2 are as defined in the description; in the formula, X1, X2, X3, X4, X5, R1, R5, R6 and R9 are as defined in the specification.

Description

【Technical field】 [0001] The present invention relates to an organic electroluminescence element (hereinafter, sometimes referred to as an organic electroluminescence element or an organic EL element) using a metal complex as a light-emitting material. 【Background technique】 [0002] Metal complexes that are luminescent materials that utilize luminescence from triplet excited states (phosphorescence) have an upper limit of internal quantum yield of 100%, so in principle they can achieve luminous efficiency four times that of luminescent materials that utilize fluorescence. Metal complexes using platinum group elements represented by iridium as metals are often used as metal complexes used in organic electroluminescent devices. [0003] In particular, iridium exists in a very small amount as a resource in the earth's crust, so there is a possibility that the resource will be exhausted, so the price is high. [0004] Therefore, various metal complexes using cheaper metals, wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07D213/18C07D233/58C08G61/00C09K11/06
CPCH01L51/0037C08G2261/5242H01L51/0035C09K11/06C08G2261/312C08G2261/3162H01L51/5012H01L51/004C08G2261/3142C09K2211/188C07D233/58C09K2211/1029C09K2211/1466C08G61/12C09K2211/1044C07D213/18C08G61/10C08G61/02H05B33/14H01L51/0091H10K85/141H10K85/111H10K85/1135H10K85/371H10K50/11H10K85/633
Inventor 仓持悠辅小林宪史东村秀之
Owner SUMITOMO CHEM CO LTD