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 comprising a ligand LA having a structure of:
• wherein:
• ring A is a 6-membered aromatic ring;
• ring D is a monocyclic or multicyclic fused ring system comprising one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
• K is selected from the group consisting of a direct bond, 0, and S;
• RA represents zero, mono, or up to a maximum allowable substitution to its associated ring;
• RD represents di or up to a maximum allowable substitution to its associated ring;
• at least two adjacent RD form a structure of Formula II fused to D;
• Z1 is selected from the group consisting of O, S, Se, NR, and SiRR′;
• Z2 is N;
• if ring D is benzene, then neither Z1 nor Z2 are fused to D at the carbon ring atom adjacent to the carbon ring atom that bonds to K;
• each RA, RB, RD, R, and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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;
• the ligand LA complexes to a metal M through the dashed lines to form a 5-membered chelate ring;
• M is Ir;
• M can be coordinated to other ligands;
• LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
• any two of RA, RB, RD, R, and R′ can be joined or fused to form a ring;
• at least one of the following is true:
• (1) ring D is a multicyclic fused ring system wherein the ring of said multicyclic fused ring system that is directly coordinated to M is a 6-membered carbocyclic ring, and wherein Formula II is directly fused to a 6-membered ring of said multicyclic fused ring structure that is not directly coordinated to M,
• (2) ring D is benzene, and a Z1 or Z2 is bonded to an atom ortho to the bond with ring A,
• (3) ring D is benzene, and Z1 or Z2 is bonded para to the bond with metal M,
• (4) at least one RA or RB comprises a moiety selected from at least two rings that are not fused together, partially or fully deuterated alkyl, or partially or fully deuterated cycloalkyl, or
• (5) K is O or S;
• and
• if condition (1), condition (2), condition (3), or condition (4) is true, then the compound has a formula selected from the group consisting of Ir(LA)(LB)2, Ir(LA)2(LB), and Ir(LA)(LB)(LC), wherein LC is a bidentate ligand, wherein LA, LB, and LC are different from each other, and wherein LB is selected from the group consisting of
• wherein:
• T is B, Al, Ga, or In;
• each of Y1 to Y13 is independently selected from the group consisting of C and N;
• Y′ is selected from the group consisting of BRe, NRe, PRe, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf;
• each Ra, Rb, Rc, and Rd independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
• each of Ra1, Rb1, Rc1, Rd1, Ra, Rb, Rc, Rd, Re and Rf is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• the general substituents defined herein;
• and
• any two adjacent Ra, Rb, Rc, Rd, Re and Rf can be fused or joined to form a ring or form a multidentate ligand.

A consumer product comprising an organic light emitting device comprising:

• an anode;
• a cathode;
• and
• an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand LA having a structure of Formula I:
• wherein:
• ring A is a 6-membered aromatic ring;
• ring D is a monocyclic or multicyclic fused ring system comprising one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
• K is selected from the group consisting of a direct bond, 0, and S;
• RA represents zero, mono, or up to a maximum allowable substitution to its associated ring;
• RD represents di or up to a maximum allowable substitution to its associated ring;
• at least two adjacent RD form a structure of Formula II fused to D;
• Z1 is selected from the group consisting of O, S, Se, NR, and SiRR′;
• Z2 is N;
• if ring D is benzene, then neither Z1 nor Z2 are fused to D at the carbon ring atom adjacent to the carbon ring atom that bonds to K;
• each RA, RB, RD, R, and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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;
• the ligand LA complexes to a metal M through the dashed lines to form a 5-membered chelate ring;
• M is Ir;
• M can be coordinated to other ligands;
• LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
• any two of RA, RB, RD, R, and R′ can be joined or fused to form a ring;
• at least one of the following is true:
• (1) ring D is a multicyclic fused ring system wherein the ring of said multicyclic fused ring system that is directly coordinated to M is a 6-membered carbocyclic ring, and wherein Formula II is directly fused to a 6-membered ring of said multicyclic fused ring structure that is not directly coordinated to M,
• (2) ring D is benzene, and a Z1 or Z2 is bonded to an atom ortho to the bond with ring A,
• (3) ring D is benzene, and Z1 or Z2 is bonded para to the bond with metal M,
• (4) at least one RA or RB comprises a moiety selected from at least two rings that are not fused together, partially or fully deuterated alkyl, or partially or fully deuterated cycloalkyl, or
• (5) K is O or S;
• and
• if condition (1), condition (2), condition (3), or condition (4) is true, then the compound has a formula selected from the group consisting of Ir(LA)(LB)2, Ir(LA)2(LB), and Ir(LA)(LB)(LC), wherein LC is a bidentate ligand, wherein LA, LB, and LC are different from each other, and wherein LB is selected from the group consisting of
• wherein:
• T is B, Al, Ga, or In;
• each of Y1 to Y13 is independently selected from the group consisting of C and N;
• Y′ is selected from the group consisting of BRe, NRe, PRe, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf;
• each Ra, Rb, Rc, and Rd independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
• each of Ra1, Rb1, Rc1, Rd1, Ra, Rb, Rc, Rd, Re and Rf is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, the general substituents defined herein;
• and
• any two adjacent Ra, Rb, Rc, Rd, Re and Rf can be fused or joined to form a ring or form a multidentate ligand.