Organic electroluminescent materials and devices

An organic light emitting device (OLED) comprising:

• an anode;
• a cathode;
• and
• an organic layer, disposed between the anode and the cathode, comprising a compound having a structure selected from the group consisting of:
• wherein X1 to X20 are each independently selected from the group consisting of carbon and nitrogen;
• wherein in Formula I, rings A, B, and C are each independently a 5- or 6-membered aromatic ring, and all are fused to ring D and form a first ligand having an 18-π electronic system;
• wherein one of the rings A, B, and C is a 5-membered aromatic ring, and the remaining rings A, B, and C are each independently a 6-membered aromatic ring;
• wherein in Formula II, ring E is a 5-membered aromatic ring, ring F is a 5- or 6-membered aromatic ring, the structure formed by ring E and ring F connected together forms a first ligand in Formula II;
• wherein RA, RB, RC, RE, and RF each independently represents none to a maximum possible number of substitutions;
• wherein RA, RB, RC, RE, RF, and L2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• wherein any substitutions in RA, RB, RC, RE, and RF are optionally joined or fused into a ring;
• wherein M1 is a metal having atomic weight greater than 40;
• wherein M2 is selected from the group consisting of B, Al, Ga, Si, Ge, Sn, Zn, Cd, Pd, Pt, Co, Rh, Ir, Re, Ru, Os, Cu, Ag, and Au;
• wherein M1 and M2 are different;
• wherein in Formula I, M2 coordinates to at least one of X10 and X11, and in Formula II, M2 coordinates to at least one of X16 and X20;
• wherein when the compound has the structure of Formula I and M2 is B, L2 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• wherein m and n have a value of at least 1 and m+n is the maximum possible number of ligands that are attached to M1;
• wherein k has a value of at least 1 and is the maximum possible number of ligands L2 that can be attached to M2;
• wherein each L1 is a bidentate ligand;
• and
• wherein the first ligand is optionally linked with L1 to comprise a mutidentate ligand.

A consumer product comprising an organic light-emitting device (OLED) comprising:

• an anode;
• a cathode;
• and
• an organic layer, disposed between the anode and the cathode, comprising a compound having a structure selected from the group consisting of:
• wherein X1 to X20 are each independently selected from the group consisting of carbon and nitrogen;
• wherein in Formula I, rings A, B, and C are each independently a 5- or 6-membered aromatic ring, and all are fused to ring D and form a first ligand having an 18-π electronic system;
• wherein one of the rings A, B, and C is a 5-membered aromatic ring, and the remaining rings A, B, and C are each independently a 6-membered aromatic ring;
• wherein in Formula II, ring E is a 5-membered aromatic ring, ring F is a 5- or 6-membered aromatic ring, the structure formed by ring E and ring F connected together forms a first ligand in Formula II;
• wherein RA, RB, RC, RE, and RF each independently represents none to a maximum possible number of substitutions;
• wherein RA, RB, RC, RE, RF, and L2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• wherein any substitutions in RA, RB, RC, RE, and RF are optionally joined or fused into a ring;
• wherein M1 is a metal having atomic weight greater than 40;
• wherein M2 is selected from the group consisting of B, Al, Ga, Si, Ge, Sn, Zn, Cd, Pd, Pt, Co, Rh, Ir, Re, Ru, Os, Cu, Ag, and Au;
• wherein M1 and M2 are different;
• wherein in Formula I, M2 coordinates to at least one of X10 and X11, and in Formula II, M2 coordinates to at least one of X16 and X20;
• wherein when the compound has the structure of Formula I and M2 is B, L2 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• wherein m and n have a value of at least 1 and m+n is the maximum possible number of ligands that are attached to M1;
• wherein k has a value of at least 1;
• wherein each L1 is a bidentate ligand;
• wherein the first ligand is optionally linked with L1 to comprise a mutidentate ligand;
• and
• wherein the consumer product is one of flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, and a sign.