IP Library › Granted Patent US 8,703,301

Granted Patent B2

US 8,703,301 · App. 12/435,762 · Granted Apr 22, 2014

Organic light emitting device comprising layer comprising organic-metal complex and method of preparing the same

Inventors: O-hyun Kwon (Seoul, KR); Sang-hoon Park (Seongnam-si, KR); Byoung-ki Choi (Hwaseong-si, KR); Dong-woo Shin (Seoul, KR)

Assignee: Samsung Display Co., Ltd.

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Quick Facts

Patent No.: US 8,703,301
App. No.: 12/435,762
Granted: Apr 22, 2014
Kind: B2

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Abstract

Provided are an organic light emitting device including a substrate; a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a first layer including an organic-metal complex represented by Formula 1 below, and a method of preparing the same: wherein Formula 1 is described in the description of the invention.

Claims (121)

1. An organic light emitting device comprising:

a substrate;

a first electrode;

a second electrode; and

an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises a first layer consisting essentially of an organic-metal complex wherein the organic-metal complex of the first layer is a compound selected from the group consisting of:

M(quinolato)(4-[4-(9,10-di-phenyl-2-yl-anthracene-2-yl)-phenyl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3,5-diphenyl-4-[4-(6-phenyl-anthracene-2-yl)-phenyl]-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-phenyl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-thiophene-2-yl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-furan-2-yl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-pyrrole-2-yl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-diphenyl-anthracene-2-yl)-phenyl]-3,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-phenyl]-3,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-di-naphthalene-anthracene-2-yl)-phenyl]-3,5-di-naphthalene-1-yl-4H-[1,2,4]triazole),

M(quinolato)(2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-5-(3,5-diphenyl-[1,2,4]triazole-4-yl)-pyridine),

M(quinolato)(3-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-6-(3,5-diphenyl-[1,2,4]triazole-4-yl)-pyridine),

M(quinolato)(5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-2-(3,5-diphenyl-[1,2,4]triazole-4-yl)-pyrimidine),

M(quinolato)(3-[4-(9,10-di-phenyl-2-yl-anthracene-2-yl)-phenyl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4,5-diphenyl-4-[4-(6-phenyl-anthracene-2-yl)-phenyl]-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-phenyl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-thiophene-2-yl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-furan-2-yl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-pyrrole-2-yl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-diphenyl-anthracene-2-yl)-phenyl]-4,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-phenyl]-4,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-di-naphthalene-anthracene-2-yl)-phenyl]-4,5-di-naphthalene-1-yl-4H-[1,2,4]triazole),

M(quinolato)(2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-5-(4,5-diphenyl-[1,2,4]triazole-3-yl)-pyridine),

M(quinolato)(3-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-6-(4,5-diphenyl-[1,2,4]triazole-3-yl)-pyridine),

M(quinolato)(5-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-2-(4,5-diphenyl-[1,2,4 ]triazole-3-yl)-pyrimidine),

M(quinolato)(4-[4-(4,9-diphenyl-pyrene-2-yl)-phenyl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3,5-diphenyl-4-[4-(6-phenyl-pyrene-2-yl)-phenyl]-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-phenyl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-thiophene-2-yl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-furan-2-yl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-pyrrole-2-yl]-3,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-diphenyl-pyrene-2-yl)-phenyl]-3,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-phenyl]-3,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(4-[4-(9,10-di-naphthalene-pyrene-2-yl)-phenyl]-3,5-di-naphthalene-1-yl-4H-[1,2,4]triazole),

M(quinolato)(2-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-5-(3,5-diphenyl-[1,2,4]triazole-4-yl)-pyridine),

M(quinolato)(3-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-6-(3,5-diphenyl-[1,2,4]triazole-4-yl)-pyridine),

M(quinolato)(5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-2-(3,5-diphenyl-[1,2,4]triazole-4-yl)-pyrimidine),

M(quinolato)(3-[4-(9,10-di-phenyl-2-yl-pyrene-2-yl)-phenyl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(4,5-diphenyl-4-[4-(6-phenyl-pyrene-2-yl)-phenyl]-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-phenyl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-thiophene-2-yl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-furan-2-yl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-pyrrole-2-yl]-4,5-diphenyl-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-diphenyl-pyrene-2-yl)-phenyl]-4,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-phenyl]-4,5-di-naphthalene-2-yl-4H-[1,2,4]triazole),

M(quinolato)(3-[4-(9,10-di-naphthalene-pyrene-2-yl)-phenyl]-4,5-di-naphthalene-1-yl-4H-[1,2,4]triazole),

M(quinolato)(2-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-5-(4,5-diphenyl-[1,2,4]triazole-3-yl)-pyridine),

M(quinolato)(3-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-6-(4,5-diphenyl-[1,2,4]triazole-3-yl)-pyridine), and

M(quinolato)(5-(9,10-di-naphthalene-2-yl-pyrene-2-yl)-2-(4,5-diphenyl-[1,2,4]triazole-3-yl)-pyrimidine),

and wherein M is an alkali metal.

2. The organic light emitting device of claim 1 , wherein M is Li or Na.

3. The organic light emitting device of claim 1 , wherein the first layer is one of an electron transport layer or a hole blocking layer.

4. A method of preparing an organic light emitting device, the method comprising:

forming a first electrode on a substrate;

forming an organic layer comprising a first layer consisting essentially of an organic-metal complex on the first electrode; and

forming a second electrode on the organic layer, wherein the organic-metal complex of the first layer is a compound selected from the group consisting of: