Tridentate platinum (II) complexes

• US 8,389,725 B2
• Filed: 02/27/2009
• Issued: 03/05/2013
• Est. Priority Date: 02/29/2008
• Status: Active Grant

• Current Assignee: Arizona Board of Regents (University of Arizona)
• Original Assignee: Arizona Board of Regents (University of Arizona)
• Inventors: Li, Jian, Wang, Zixing, Turner, Eric
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US12/919,899
• Publication Number:
  US 20110028723A1
• Time in Patent Office: 1,467 Days
• Field of Search: 546/2, 546/10, 428/690, 313/504
• US Class Current: 546/2
• CPC Class Codes: C07F 15/00 Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/00 Organic light-emitting devices integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/346 comprising platinum

Abstract

A platinum (II) complex of general formula (II)

in which Ar1, Ar2, and Ar3 are each independently aryl, heteroaryl, or heterocyclic. Ar1, Ar2, and Ar3 together form a tridentate ligand coordinated to the platinum through atoms X, Y, and Z, respectively, and X, Y, and Z are independently carbon or nitrogen. V is a bridging group, and W is an anion. The complexes emit in the UV to near IR range and are useful as emitters for organic light emitting devices.

Claims

1. A platinum (II) complex of the formula

2. The complex of claim 1, wherein each of Ar1, Ar2, and Ar3 is independently unsubstituted or substituted with one more R groups, wherein each R group independently represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.

3. A phosphorescent emitter comprising the complex of claim 1.

4. An organic light emitting device comprising the complex of claim 1.

5. The complex of claim 1, wherein W is chlorine.

6. The complex of claim 1, wherein —

W is —

C≡

C—

R, and R represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.

7. The complex of claim 1, wherein —

W is —

C═

C—

R, and R represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.

8. The complex of claim 1, wherein —

W is —

O—

R, and R represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.

9. The complex of claim 1, wherein —

W is —

S—

R, and R represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.

10. The complex of claim 1, wherein —

W is —

NR₂, and each R independently represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.

11. The complex of claim 1, wherein —

W is —

PR₂, and each R independently represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.

12. The complex of claim 1, wherein W is an unsubstituted aryl or heteroaryl group.

13. The complex of claim 1, wherein W is an aryl or heteroaryl group substituted with one or more R groups, wherein each R group independently represents an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, an ureido group, a phosphoramide group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, or a polymerizable group.