Organic electroluminescent materials and devices

A compound comprising the formula Ir(LA)x(LB)y(LC)z, wherein:

• x and y are each independently 1 or 2;
• z is 0 or 1;
• x
• +
• y
• +
• z
• =
• 3
• ;
• ligand LA comprises a structure of Formula I,
• ligand LB comprises a structure of Formula II,
• ligand LC is a bidentate ligand;
• each of X1 to X14 is independently C or N;
• the one of X5 to X8 bonded to the ring comprising X3 and X4 is C;
• Y is selected from the group consisting of BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CR, CRR′, SiRR′, and GeRR′;
• each of RA, RB, RC, RD, and RE independently represents mono to the maximum allowable substitutions, or no substitutions;
• each R1, R2, R3, RD and RE is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryloxy, amino, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, silyl, germyl, and combinations thereof;
• each of R, R′, RA1, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
• two RB groups or two RC groups can be joined to form a fused carbocyclic or heterocyclic ring;
• R4 comprises a tertiary or secondary alkyl group and can further comprise one or more moieties where each moiety is independently selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryloxy, amino, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, silyl and germyl group, and combinations thereof;
• the dashed lines indicate coordination to Ir;
• and
• any two of R1, R2, R3, R4, R, R′, RA1, RA, RB, RC, RD and RE may be joined or fused to form a ring.

An organic light emitting device (OLED) comprising:

• an anode;
• a cathode;
• and
• an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising the formula Ir(LA)x(LB)y(LC)z, wherein:
• x and y are each independently 1 or 2,
• z is 0 or 1,
• x
• +
• y
• +
• z
• =
• 3
• ;
• ligand LA comprises a structure of Formula I,
• ligand LB comprises a structure of Formula II
• ligand LC is a bidentate ligand;
• each of X1 to X14 is independently C or N;
• the one of X5 to X8 bonded to the ring comprising X3 and X4 is C;
• Y is selected from the group consisting of BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CR, CRR′, SiRR′, and GeRR′;
• each of RA, RB, RC, RD, and RE independently represents mono to the maximum allowable substitutions, or no substitutions;
• each R1, R2, R3, RD and RE is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryloxy, amino, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, silyl, germyl, and combinations thereof;
• each of R, R′, RA1, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
• two RB groups or two RC groups can be joined to form a fused carbocyclic or heterocyclic ring;
• R4 comprises a tertiary or secondary alkyl group and can further comprise one or more moieties where each moiety is independently selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryloxy, amino, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, silyl and germyl group, and combinations thereof;
• the dashed lines indicate coordination to Ir;
• and
• any two of RI, R2, R3, R4, R, R′, RA1, RA, RB, RC, RD and RE may be joined or fused to form a ring.

A compound, or a neutral molecular form thereof, or a monovalent or polyvalent form thereof, or a monomeric or polymeric form thereof, or a macromolecular or supramolecular form thereof wherein the compound comprises the formula Ir(LA)x(LB)y(LC)z, wherein:

• x and y are each independently 1 or 2;
• z is 0 or 1;
• x
• +
• y
• +
• z
• =
• 3
• ;
• ligand LA comprises a structure of Formula I,
• ligand LB comprises a structure of Formula II,
• ligand LC is a bidentate ligand;
• each of X1 to X14 is independently C or N;
• the one of X5 to X8 bonded to the ring comprising X3 and X4 is C;
• Y is selected from the group consisting of BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CR, CRR′, SiRR′, and GeRR′;
• each of RA, RB, RC, RD, and RE independently represents mono to the maximum allowable substitutions, or no substitutions;
• each R1, R2, R3, RD and RE is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryloxy, amino, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, silyl, germyl, and combinations thereof;
• each of R, R′, RA1, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
• two RB groups or two RC groups can be joined to form a fused carbocyclic or heterocyclic ring;
• R4 comprises a tertiary or secondary alkyl group and can further comprise one or more moieties where each moiety is independently selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryloxy, amino, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, silyl and germyl group, and combinations thereof;
• the dashed lines indicate coordination to Ir;
• and
• any two of R1, R2, R3, R4, R, R′, RA1, RA, RB, RC, RD and RE may be joined or fused to form a ring.