IP Library Granted Patent US 9,966,544
Granted Patent B2
US 9,966,544 · App. 14/211,190 · Granted May 8, 2018

Phosphorescent metal complex compound radiation emitting component comprising a phosphorescent metal complex compound and method for production of a phosphorescent metal complex compound

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Quick Facts
Patent No.
US 9,966,544
App. No.
14/211,190
Granted
May 8, 2018
Kind
B2
Abstract

A phosphorescent metal complex is provided, which comprises a metallic central atom M and at least one ligand coordinated by the metallic central atom M, wherein the one metallic central atom M and the ligand form a six-membered metallacyclic ring. Additionally specified are a radiation-emitting component comprising a metal complex, and a process for preparing the metal complex.

Claims (56)

1. A phosphorescent polynuclear metal complex which comprises at least two metallic central atoms M, that are bonded to one another via at least one bridging bidentate ligand that coordinates by one bonding atom to one central atom and another bonding atom to another central atom, and at least one ligand coordinated by one metallic central atom M, wherein the at least one bridging bidentate ligand is 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine, wherein one of the metallic central atoms M and the ligand form a six-membered metallacyclic ring,

wherein the ligand which forms a six-membered metallacyclic ring with the metallic central atom has a tautomerizable unit in the uncoordinated state,

wherein the metallic central atom M is selected from a group consisting of Ir, Pt, Au, Re, Rh, Ru, Os, Pd, Ag, Zn, Al and lanthanoids, and

wherein the six-membered metallacyclic ring has the structural formula:

where:

n=1 to 3,

Y=C—H, N, P, As, Sb, C—R y , Si—R y , Ge—R y ,

X=N, O, P, As, Sb,

R 1 , R 2 , R y , R 4 and R 5 are each independently H, unbranched alkyl radicals, branched alkyl radicals, fused alkyl radicals, cyclic alkyl radicals, fully or partly substituted unbranched alkyl radicals, fully or partly substituted branched alkyl radicals, fully or partly substituted fused alkyl radicals, fully or partly substituted cyclic alkyl radicals, alkoxy groups, amines, amides, esters, carbonates, aromatics, fully or partly substituted aromatics, fused aromatics, fully or partly substituted fused aromatics, heterocycles, fully or partly substituted heterocycles, fused heterocycles, fully or partly substituted heterocycles, F and CN, and

R 1 and R 5 include a free electron pair when X is O.

2. The complex of claim 1 , wherein R 1 and/or R 5 is additionally coordinated to M.

3. The complex of claim 1 , wherein at least one of R 1 and R 2 , R 2 and R y , R y and R 4 , R 4 and R 5 are bridged to one another.

4. The complex of claim 3 , wherein the six-membered metallacyclic ring has a structural formula selected from a group consisting of compounds of the following structural formula:

where:

n=1 to 3,

Y=C—H, N, P, As, Sb, C—R y , Si—R y , Ge—R y ,

X=N, O, P, As, Sb,

X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 are each independently C or, when R 11 , R 12 , R 3 , R 14 , R 15 , R 6 , R 7 or R 8 includes a free electron pair, N, and

R y , R 11 , R 12 , R 3 , R 14 , R 15 , R 6 , R 7 and R 8 are each independently H, unbranched alkyl radicals, branched alkyl radicals, fused alkyl radicals, cyclic alkyl radicals, fully or partly substituted unbranched alkyl radicals, fully or partly substituted branched alkyl radicals, fully or partly substituted fused alkyl radicals, fully or partly substituted cyclic alkyl radicals, alkoxy groups, amines, amides, esters, carbonates, aromatics, fully or partly substituted aromatics, fused aromatics, fully or partly substituted fused aromatics, heterocycles, fully or partly substituted heterocycles, fused heterocycles, fully or partly substituted heterocycles, F and CN.

5. The complex of claim 4 , wherein X 1 ═X 5 , R 11 ═R 15 , X 2 ═X 6 , R 12 ═R 6 , X 3 ═X 7 , R 3 ═R 7 , X 4 ═X 8 and R 14 ═R 8 .

6. The complex of claim 4 , wherein at least one of R 11 and R 12 , R 12 and R 3 , R 3 and R 14 , R 14 and R y , R y and R 8 , R 15 and R 6 , R 6 and R 7 or R 7 and R 8 are bridged to one another.

7. The complex of claim 3 , wherein the six-membered metallacyclic ring has a structural formula selected from a group consisting of compounds of the following structural formula:

where:

n=1 to 3,

Y=C—H, N, P, As, Sb, C—R y , Si—R y , Ge—R y ,

X=N, O, P, As, Sb,

X 1 , X 2 , X 5 and X 6 are each independently C or, when R 11 , R 12 , R 15 or R 6 includes a free electron pair, N,

X 3 and X 7 are each S, and

R y , R 11 , R 12 , R 15 and R 6 are each independently H, unbranched alkyl radicals, branched alkyl radicals, fused alkyl radicals, cyclic alkyl radicals, fully or partly substituted unbranched alkyl radicals, fully or partly substituted branched alkyl radicals, fully or partly substituted fused alkyl radicals, fully or partly substituted cyclic alkyl radicals, alkoxy groups, amines, amides, esters, carbonates, aromatics, fully or partly substituted aromatics, fused aromatics, fully or partly substituted fused aromatics, heterocycles, fully or partly substituted heterocycles, fused heterocycles, fully or partly substituted heterocycles, F and CN.

8. The complex of claim 7 , wherein X 1 ═X 5 , R 11 ═R 15 , X 2 ═X 6 , R 12 ═R 6 , and X 3 ═X 7 .

9. The complex of claim 7 , wherein R 11 and R 12 and/or R 15 and R 6 are bridged to one another.

10. The complex of claim 3 , wherein the six-membered metallacyclic ring has a structural formula selected from a group consisting of compounds of the following structural formula:

where:

n=1 to 3,

Y=C—H, N, P, As, Sb, C—R y , Si—R y , Ge—R y ,

X 1 , X 2 , X 3 and X 4 are each independently C—R or N, and

R y and R are each independently H, unbranched alkyl radicals, branched alkyl radicals, fused alkyl radicals, cyclic alkyl radicals, fully or partly substituted unbranched alkyl radicals, fully or partly substituted branched alkyl radicals, fully or partly substituted fused alkyl radicals, fully or partly substituted cyclic alkyl radicals, alkoxy groups, amines, amides, esters, carbonates, aromatics, fully or partly substituted aromatics, fused aromatics, fully or partly substituted fused aromatics, heterocycles, fully or partly substituted heterocycles, fused heterocycles, fully or partly substituted heterocycles, F and CN.

11. The complex of claim 1 , wherein the tautomerizable unit has a structural unit which is selected from —C(H,R y )— or —N(H)—, and connects an electron-deficient and an electron-rich aromatic.

12. The complex of claim 1 , wherein the six-membered metallacyclic ring has a structural formula selected from a group consisting of compounds of the following structural formula:

where:

n=1 to 3,

Y=C—H, N, P, As, Sb, C—R y , Si—R y , or Ge—R y ,

X and X′ are each independently N, O, P, As or Sb,

R 1 , R 2 , R 4 , R y , R 5 are each independently selected from H, unbranched alkyl radicals, branched alkyl radicals, fused alkyl radicals, cyclic alkyl radicals, fully or partly substituted unbranched alkyl radicals, fully or partly substituted branched alkyl radicals, fully or partly substituted fused alkyl radicals, fully or partly substituted cyclic alkyl radicals, alkoxy groups, amines, amides, esters, carbonates, aromatics, fully or partly substituted aromatics, fused aromatics, fully or partly substituted fused aromatics, heterocycles, fully or partly substituted heterocycles, fused heterocycles, fully or partly substituted heterocycles, F and CN, and

R 1 together with R 2 and X═C, and R 4 together with R 5 and X′—C, form at least one aromatic ring each.

13. The complex of claim 12 , wherein one of the aromatic rings formed with R 5 and R 4 and R 1 and R 2 is electron-rich, and the other aromatic ring is electron-deficient.

14. The complex of claim 12 , wherein Y is C—R y , Si—R y , or Ge—R y , and wherein R 4 and R y and/or R y and R 2 are bridged.

15. A radiation-emitting component comprising:

a substrate;

a first electrode layer on the substrate;

at least one organic emitting layer on the first electrode layer; and

a second electrode layer on the organic emitting layer,

wherein the organic emitting layer comprises a phosphorescent metal complex of claim 1 .

16. The component of claim 15 , wherein the phosphorescent metal complex is present in a matrix material.

17. The component of claim 15 , which on application of a voltage emits light of a color selected from a group consisting of deep blue, light blue, blue-green and green.

18. The component of claim 15 , wherein the substrate and the first electrode layer are transparent.

Assignments (2)
MERGER Recorded Feb 17, 2026
From: OSRAM OLED GMBH
To: AMS-OSRAM INTERNATIONAL GMBH
Reel/Frame 074881/0104 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2016
From: OSRAM OPTO SEMICONDUCTORS GMBH
To: OSRAM OLED GMBH
Reel/Frame 037567/0993 →