ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

• US 20160072082A1
• Filed: 11/05/2015
• Published: 03/10/2016
• Est. Priority Date: 05/08/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: BROOKS, Jason, SZIGETHY, Geza, DJUROVICH, Peter I., MORELLO, Glenn, DENG, Jun, CHEN, Hsiao-Fan
• Granted Patent: US 10,256,419 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: C07D 221/18 Ring systems of four or more rings
• CPC Class Codes: C07D 231/54 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 403/02 containing two hetero rings
• CPC Class Codes: C07D 471/16 Peri-condensed systems
• CPC Class Codes: C07D 498/16 Peri-condensed systems
• CPC Class Codes: C07D 513/16 Peri-condensed systems
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• 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 50/11 : characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/81 : Anodes
• CPC Class Codes: H10K 50/82 : Cathodes
• CPC Class Codes: H10K 59/00 : Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/346 : comprising platinum
• CPC Class Codes: H10K 85/60 : Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Imidazophenanthridine ligands and metal complexes are provided. The compounds exhibit improved stability through a linking substitution that links a nitrogen bonded carbon of an imidizole ring to a carbon on the adjacent fused aryl ring. The compounds may be used in organic light emitting devices, particularly as emissive dopants, providing devices with improved efficiency, stability, and manufacturing. In particular, the compounds provided herein may be used in blue devices having high efficiency.

Claims

1. A compound having a structure (L_A)_nML_m according to Formula 1:

2. The compound of claim 1, wherein the linking group A is independently selected from the group consisting of —

CR¹R²—

CR³R⁴—

, —

CR¹R²—

CR³R⁴—

CR⁵R⁶—

, —

CR¹R²—

NR³—

, —

CR¹═

CR²—

CR³R⁴—

, —

O—

SiR¹R²—

, —

CR¹R²—

S—

, —

CR¹R²—

O—

, and —

C—

SiR¹R²—

, wherein each R¹ to R⁶ can be same or different, and are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;

wherein any adjacent R¹ to R⁶ are optionally connected to form a saturated five membered ring or a saturated six membered ring.

3. The compound of claim 1, wherein the compound has a triplet excited state and wherein the linking group stabilizes the bond between N² and C^1b from cleavage when the compound is in the triplet excited state.

7. The compound of claim 2, wherein the linking group is selected from the group consisting of:

8. The compound of claim 1, wherein A is a saturated group.

13. The compound of claim 1, wherein at least one of R^1a to R^1g is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and combinations thereof.

17. The compound of claim 1, wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au.

19. The compound of claim 1, wherein the ligand L_A is selected from the group consisting of:

20. The compound of claim 1, wherein the ligand L is selected from the group consisting of:

23. The compound of claim 20, wherein the ligand L is selected from the group consisting of:

24. The compound of claim 1, wherein ligand L is selected from the group consisting of:

27. The compound of claim 19, wherein the compound is Compound Ax having the formula Ir(L_Ai)₃;

wherein x=i, i is an integer from 1 to 2758.

28. The compound of claim 19, wherein the compound is Compound By having the formula Ir(L_Ai)(L_j)₂ or Compound Cz having the formula Ir(L_Ai)₂(L_j);

wherein y=39i+j−

39, i is an integer from 1 to 2758, and j is an integer from 1 to 39;

wherein z=39i+j−

39, i is an integer from 1 to 2758, and j is an integer from 1 to 39; and

wherein L₁ to L₃₉ have the following structure;

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

30. The compound of claim 1, wherein the compound has a structure of Formula 2:

39. The compound of claim 1, wherein the compound has Formula 3:

51. A formulation comprising a compound according to claim 1.

4-6. -6. (canceled)

9-12. -12. (canceled)

14-16. -16. (canceled)

18. (canceled)

21-22. -22. (canceled)

25-26. -26. (canceled)

31-38. -38. (canceled)

40-43. -43. (canceled)

44. An organic light emitting device (OLED) comprising:

an anode;

a cathode;

an organic layer disposed between the anode and the cathode, wherein the organic layer comprising a compound having a structure (L_A)_nML_m according to Formula 1;

45. The OLED of claim 44, wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.

48. The OLED of claim 44, wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

46-47. -47. (canceled)

49-50. -50. (canceled)

52-69. -69. (canceled)