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

Patent metadata

Field	Value
Publication number	US-9966544-B2
Application number	US-201414211190-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	May 21, 2007
Publication date	May 8, 2018
Grant date	May 8, 2018

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.

First claim

The invention claimed is:

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.

Assignees

• Osram Opto Semiconductors Gmbh
• Osram Oled Gmbh

Inventors

• Adler Jürgen
• Kanitz Andreas
• Schmid Günter
• Freydenzon Oksana
• Maltenberger Anna

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09B57/10

  Metal complexes of organic compounds not being dyes in uncomplexed form · CPC title

• C09B57/007

  Squaraine dyes · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B55/009

  Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image) · CPC title