Granted Patent B2

US 11,121,328 · App. 17/008,762 · Granted Sep 14, 2021

Inventors: Jian Li (Tempe, AZ); Eric Turner (Phoenix, AZ)

Assignee: Arizona Board of Regents on behalf of Arizona State University

H01L51/0087C07F15/0086C09K11/06C09K2211/1044C09K2211/185H01L51/5016

Abstract

Claims (49)

1. A composition represented by the general formula:

wherein M is platinum or palladium;

Ar 1 is imidazole, pyrazole, pyridine, isoquinonline, or quinoline;

Ar 2 and Ar 3 are each independently phenyl or pyridine;

Ar 5 is phenyl;

Ar 6 is phenyl or is absent;

each of Ar 1 , Ar 2 , Ar 3 , Ar 5 , and Ar 6 independently is substituted or unsubstituted;

each of X 1 , X 2 and X 3 are individually coordinated to a platinum or palladium atom, and independently is a carbon or a nitrogen atom;

W is coordinated to the platinum or a palladium atom, and is a halogen atom, a nitrile group, an aryl group, a C 3 -C 6 alkynyl group, an alkenyl group, or a heteroaryl group; wherein W is optionally bonded directly or through an oxygen atom, sulfur atom, nitrogen atom, or phosphorous atom;

A represents nitrogen, carbon, boron, phosphorus, silicon, or a combination thereof, and wherein A is optionally substituted;

each of b 1 , b 2 , and b 3 individually represents a single bond, oxygen, sulfur, nitrogen, carbon, boron, phosphorus, silicon, or a combination thereof; when Ar 6 is absent, then b 2 and b 3 are not present.

2. The composition of claim 1 , wherein

represents one of the following structures:

n and I are each 1 or 0;

R 1 is H or C 1 -C 3 alkyl; and

R 3 is C 1 -C 3 alkyl.

3. The composition of claim 1 , wherein

each independently represent one of the following structures:

or a combination thereof;

wherein m is 1 or 0; and

R 2 is C 1 -C 3 alkyl.

4. The composition of claim 1 , wherein each of

independently represent the following structure:

5. The composition of claim 1 , wherein

is represented by one of the following structures:

wherein U is —C(R 2 ) 2 , —O— or —S—;

I is 0 or 1 ; and

each occurrence of R 1 , R 2 , R 4 , and R 5 is independently H or C 1 -C 3 alkyl.

6. The composition of claim 1 , wherein W is Cl, F, C 3 alkynyl, nitrile, quinazoline, isoquinoline, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.

7. The composition of claim 1 , wherein

is pyridine, isoquinoline, methylimidazole, or

8. The composition of claim 1 , wherein W is Cl, nitrile, phenyl, naphthyl or isoquinoline;

is isoquinoline, methylimidazole, or

is phenyl;

is pyridine; and

is phenyl.

9. The composition of claim 1 , wherein

represents

wherein IV is C 1 -C 3 alkyl.

10. The composition of claim 1 , wherein b 1 represents a single bond.

11. The composition of claim 1 , wherein b 2 is —S—,—S(R 1 ) 2 —, —C(R 2 ) 2 —, —O—, —NH— or —NR n —;

wherein each R 1 and R 2 is independently H or C 1 -C 3 alkyl; and

R n is C 1 -C 3 alkyl.

12. The composition of claim 1 , wherein M comprises platinum(II).

13. The composition of claim 1 , wherein M comprises palladium(II).

14. The composition of claim 1 , comprising

or a mixture thereof.

15. An organic light emitting device (OLED) comprising the compound of claim 1 .

16. A full color display comprising the OLED of claim 15 .

Assignments (1)

Continuity (5)

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