ORGANIC LIGHT EMITTING DIODE INCLUDING ORGANIC LAYER COMPRISING ORGANIC METAL COMPLEX

• US 20080111476A1
• Filed: 04/13/2007
• Published: 05/15/2008
• Est. Priority Date: 11/09/2006
• Status: Active Grant

• Current Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Original Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Inventors: Lee, Kwan-Hee, Lim, Choon-Woo, Chun, Min-Seung, Choi, Kyung-Hoon
• Granted Patent: US 9,150,783 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/187 of the iron group metals, i.e. Fe, Co or Ni
• CPC Class Codes: C09K 2211/188 of other metals not provided for in one of the previous groups
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source

Abstract

Organic light emitting diodes (OLEds) are provided. In one embodiment, an OLED includes a first electrode, a second electrode and an organic layer positioned between the first and second electrodes. The organic layer comprises an organic metal complex represented by the formula [M(L)₂]_a, in which L is an anionic ligand, M is a metal that can be five-coordinated or six-coordinated with L, and a is an integer ranging from 2 to 4.

Claims

1. An organic light emitting diode comprising:

a first electrode;

a second electrode; and

an organic layer positioned between the first and second electrodes, wherein the organic layer comprises an organic metal complex represented by Formula 1;

[M(L)₂]_a  

 

Formula (1)

wherein L is an anionic ligand, M is a metal that can be five-coordinated or six-coordinated with L, and a is an integer ranging from 2 to 4.

2. The organic light emitting diode of claim 1, wherein M is selected from the group consisting of Zn, Ni, Co and Fe.

3. The organic light emitting diode of claim 1, wherein L is selected from the group consisting of ligands represented by Formulae 2 and 3:

wherein each of A, B, C and D is independently selected from the group consisting of aromatic rings having from 5 to 20 ring members, and heteroaromatic rings having from 5 to 20 ring members, wherein each of X₁, X₂, X₃ and X₄ is independently selected from the group consisting of C, N, O, S or P, and * is a site that binds M.

4. The organic light emitting diode of claim 3, wherein A and B are bound to each other, and C and D are bound to each other.

5. The organic light emitting diode of claim 3, wherein A and B are fused with each other, and C and D are fused with each other.

6. The organic light emitting diode of claim 1, wherein each of A, B, C and D is independently selected from the group consisting of benzene, pentalene, indene, naphthalene, azulene, heptalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, hecacene, pyrrole, imidazole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, indazole, purine, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, perimidine, phenanthroline, phenazine, phenothiazine, phenoxazine, benzothiazole, benzooxazole and benzoimidazole.

7. The organic light emitting diode of claim 3, wherein each of A and B is independently selected from the group consisting of benzene and naphthalene.

8. The organic light emitting diode of claim 3, wherein each of C and D is independently selected from the group consisting of pyridine, benzothiazole, benzooxazole, quinoline and benzoimidazole.

9. The organic light emitting diode of claim 1, wherein the organic metal complex represented by Formula 1 is selected from the group consisting of complexes represented by Formulae 4, 5 and 6:

10. The organic light emitting diode of claim 1, wherein the organic metal complex represented by Formula 1 is represented by Formula 7:

11. An organic light emitting diode comprising:

a first electrode;

a second electrode; and

an organic layer positioned between the first and second electrodes, wherein the organic layer comprises an emissive layer comprising an organic metal complex represented by Formula 1;

[M(L)₂]_a  

 

Formula (1)

wherein L is an anionic ligand, M is a metal that can be five-coordinated or six-coordinated with L, and a is an integer ranging from 2 to 4.

12. The organic light emitting diode of claim 11, wherein the emissive layer further comprises a phosphorescent dopant.

13. The organic light emitting diode of claim 12, wherein the phosphorescent dopant comprises an organic metal complex comprising a metal selected from the group consisting of Ir, Pt, Os, Re, Ti, Zr and Hf.

14. The organic light emitting diode of claim 12, wherein the phosphorescent dopant comprises an organic metal complex comprising a metal selected from the group consisting of Ir and Pt.

15. The organic light emitting diode of claim 12, wherein the phosphorescent dopant is selected from the group consisting of bisthienylpyridine acetylacetonate Iridium, bis(benzothienylpyridine)acetylacetonate Iridium, bis(2-phenylbenzothiazole)acetylacetonate Iridium, bis(1-phenylisoquinoline) Iridium acetylacetonate, tris(1-phenylisoquinoline) Iridium, tris(phenylpyridine) Iridium, tris(2-biphenylpyridine) Iridium, tris(3-biphenylpyridine) Iridium, tris(4-biphenylpyridine) Iridium, Ir(pq)₂(acac) represented by Formula 8 where pq is 2-phenylquinoline and acac is acetylacetone, Ir(ppy)₃ represented by Formula 9 where ppy is phenyl pyridine, platinum(II)octaethylporphyrin (PtOEP), compounds represented by Formula 10, Firpic represented by Formula 11, Ir(piq)₃ represented by Formula 12, Ir(piq)₂acac represented by Formula 13 where piq is phenylisoquinoline, compounds represented by Formula 14, compounds represented by Formula 15, compounds represented by Formula 16, compounds represented by Formula 17 and combinations thereof:

16. The organic light emitting diode of claim 11, wherein the emissive layer further comprises at least one host selected from the group consisting of CBP, Alq3, BAlq and Bebq.

17. The organic light emitting diode of claim 16, wherein the at least one host is present in an amount ranging from about 50 to about 150 parts by weight based on 100 parts by weight of the organic metal complex represented by Formula 1.

18. The organic light emitting diode of claim 11, wherein the organic layer further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer.