IP Library Granted Patent US 10,930,865
Granted Patent B2
US 10,930,865 · App. 16/199,682 · Granted Feb 23, 2021

Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof

Inventors: Jian Li (Tempe, AZ); Zhi-Qiang Zhu (Mesa, AZ)
Assignee: Arizona Board of Regents on behalf of Arizona State University
H01L51/0087C07F15/0086C09K11/06H01L51/0093C09K2211/1022C09K2211/1029C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 10,930,865
App. No.
16/199,682
Granted
Feb 23, 2021
Kind
B2
Abstract

The complexes disclosed herein are cyclometalated metal complexes of Formula (I) that are useful for full color displays and lighting applications.

Claims (37)

1. A complex of Formula I:

wherein:

M is Pt or Pd;

ring A and ring B each independently represents substituted or unsubstituted 5 or 6-membered aryl, or substituted or unsubstituted 5 or 6-membered heteroaryl having one or more U heteroatoms or one or more U1 heteroatoms, wherein U and U1 are each independently selected from N, P, As, O, S, and Se;

Y 1a , Y 1b and Y 1c each independently represents O, S, S(O), S(O) 2 , Se, Se(O), Se(O) 2 , N, NR 5a , P, PR 5a , As, AsR 5a , O═NR 5a , O═PR 5a , O═AsR 5a , B, BR 5a , SiR 5a , SiR 5b R 5c , CR 5a , or CR 5b R 5c ;

Y 2a , Y 2b , Y 2c and Y 2d each independently represents C or N;

Y 3a , Y 3b , Y 3c , Y 3d Y 4a , Y 4b , Y 4c , and Y 4d each independently represents C, N, Si, O, or S;

R 1 , R 2 , R 3 , and R 4 each independently represents hydrogen, halogen, hydroxy, amino, nitro, thiol, Si(C 1 -C 4 alkyl) 3 , substituted or unsubstituted C 1 -C 4 alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocycloalkyl;

R 5a , R 5b , and R 5c each independently represents hydrogen, substituted or unsubstituted C 1 -C 4 alkyl, or substituted or unsubstituted aryl;

each of L 1 , L 2 , L 3 , L 4 , L 5 and L 6 independently is absent, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl,

is independently

is independently

is independently

wherein X 1 , X 2 , X 3 , X 4 , X 5 and X 6 each independently is absent or represents a bond, O, S, S(O), S(O) 2 , Se, Se(O), Se(O) 2 , NR 7a , P, PR 7a , As, AsR 7a , O═NR 7a , O═PR 7a , O═AsR 7a , B, BR 7a , SiR 7a R 7b , or CR 7a R 7b ;

R 7a and R 7b each independently represents hydrogen, substituted or unsubstituted C 1 -C 4 alkyl, or substituted or unsubstituted aryl;

R 5 , R 6 and R 7 each independently represents hydrogen, halogen, hydroxy, amino, nitro, thiol, Si(C 1 -C 4 alkyl) 3 , substituted or unsubstituted C 1 -C 4 alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocycloalkyl;

m, n, o, and p each independently represents 1, 2, or 3; and

t, u, and v each independently represents 1, 2, 3, 4, or 5.

2. The complex of claim 1 having a formula selected from:

3. The complex of claim 1 having Formula IIa:

4. The complex of claim 1 having Formula IIIa:

5. The complex of claim 1 having Formula IIb:

6. The complex of claim 1 having Formula IIIb:

7. The complex of claim 1 having Formula IVb:

8. The complex of claim 1 , wherein M is Pt.

9. The complex of claim 1 , wherein R 1 , R 2 , R 3 and R 4 each independently represents hydrogen, halogen, hydroxy, amino, substituted or unsubstituted C 1 -C 4 alkyl, or substituted or unsubstituted alkoxy.

10. The complex of claim 1 , wherein R 3 and R 4 are each independently substituted or unsubstituted C 1 -C 4 alkyl.

11. The complex of claim 1 , wherein R 1 and R 2 are hydrogen.

12. The complex of claim 1 , wherein R 5 , R 6 , and R 7 each independently represents hydrogen, halogen, hydroxy, amino, substituted or unsubstituted C 1 -C 4 alkyl, or substituted or unsubstituted alkoxy.

13. The complex of claim 1 , wherein R 5 , R 6 , and R 7 are hydrogen.

14. The complex of claim 1 , wherein Y 1a is O.

15. The complex of claim 1 , wherein Y 1b is N.

16. The complex of claim 1 , wherein Y 1c is N.

17. The complex of claim 1 , wherein Y 2a , Y 2c , Y 2b , and Y 2d are C.

18. The complex of claim 1 , wherein Y 3d and Y 4d are N, and Y 3c and Y 4c are C.

19. A complex which is

20. A light emitting device comprising the complex of claim 1 .

Continuity (3)
Continuation 15228401 · Aug 4, 2016
Provisional Application 62200960 · Aug 4, 2015
Related Publication 20190259963A1 · Aug 22, 2019
Cited By (9)
US 12,193,327 US 12,302,745 US 12,312,366 US 12,448,405 US 12,503,644 US 12,534,462 US 12,545,678 US 12,565,486 US 12,643,919