Cyclometallated Tetradentate Pt (II) Complexes

• US 20130048963A1
• Filed: 08/13/2012
• Published: 02/28/2013
• Est. Priority Date: 08/31/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Beers, Scott, Xia, Chuanjun, Brooks, Jason, Kottas, Gregg
• Granted Patent: US 9,493,698 B2
• Time in Patent Office: Days
• US Class Current: 257/40
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/18 characterised by the nature or concentration of the activator
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/346 comprising platinum

Abstract

Novel phosphorescent tetradentate platinum (II) compounds are provided. The compounds contain an isoimidazole moiety, optionally further substituted with a twisted aryl. These compounds may be advantageously used in OLEDs.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein R₅ is a substituted aryl.

3. The compound of claim 1, wherein R₅ is a 2,6-disubstituted aryl.

4. The compound of claim 1, wherein R₅ is

wherein R′

₁ and R′

₂ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one of R′

₁ and R′

₂ is not hydrogen or deuterium;

wherein D is 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted with R′

₃; and

wherein R′

₃ is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

6. The compound of claim 4, wherein at least one of R′

₁ and R′

₂ is an alkyl.

7. The compound of claim 4, wherein each of R′

₁ and R′

₂ is an alkyl.

8. The compound of claim 4, wherein at least one of R′

₁ and R′

₂ is an alkyl containing at least 2 carbons.

9. The compound of claim 4, wherein at least one of R′

₁ and R′

₂ is an aryl.

10. The compound of claim 4, wherein each of R′

₁ and R′

₂ is an aryl.

36. The compound of claim 1, wherein the compound has the formula:

37. The compound of claim 1, wherein the compound has the formula:

38. The compound of claim 1, wherein the compound has the formula:

39. The compound of claim 1, wherein the compound has the formula:

40. The compound of claim 1, wherein the compound has the formula:

41. The compound of claim 1, wherein the compound has the formula:

42. The compound of claim 1, wherein L₁ or L₃ is selected from the group consisting of O, S, CH₂, CR′

₂, NR′

, SiR′

₂ or BR; and

wherein R′

is alkyl or aryl.

43. The compound of claim 1, wherein L₂ is selected from the group consisting of O, S, CH₂, CR′

₂, NR′

, and SiR′

₂;

wherein R′

is alkyl or aryl; and

wherein R′

is optionally bonded to B or C.

44. The compound of claim 1, wherein R₁, R₂, R₃ and R₄ are each independently selected from the group consisting of hydrogen, deuterium, alkyl, aryl, cyclic alkyl, branched alkyl, heteroaryl, and fused aryl.

45. The compound of claim 1, wherein the compound is selected from the group consisting of

5. (canceled)

11-35. -35. (canceled)

46. A first device comprising a first organic light emitting device, further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula;