Organic electroluminescent materials and devices

A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:

• an anode;
• a cathode;
• and
• an organic layer, disposed between the anode and the cathode, comprising a compound having a formula M(LA)x(LB)y(LC)z:
• wherein the ligand LA is
• wherein the ligand LB is
• wherein the ligand LC is
• wherein M is a metal having an atomic number greater than 40;
• wherein x is 1, or 2;
• wherein y is 0, 1, or 2;
• wherein z is 0, 1, or 2;
• wherein x+y+z is the oxidation state of the metal M;
• wherein A1, A2, A3, A4, A5, A6, A7, and A8 are carbon or nitrogen;
• wherein ring B is bonded to ring A through a C—C bond;
• wherein M is bonded to ring A through a M-C bond;
• wherein X is selected from the group consisting of O, S, Se, CRR′, and NR1;
• wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
• wherein R3 represents mono, or di-substitution, or no substitution;
• wherein R2, RC, and RD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
• wherein R4 represents mono, di, tri, or tetra-substitution;
• wherein at least one R4 is a five-membered or six-membered heterocyclic ring which can be further substituted by RE;
• wherein RE represents mono, di, tri, or tetra-substitutions, or no substitutions;
• wherein each of R, R′, R1, R2, R3, R4, RC, RD, RX, RY, RZ and RE 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 any adjacent substituents of R, R′, RX, RY, and RZ are optionally joined to form a ring;
• and any two adjacent R1, R2, R3, R4, RC, RD, and RE are optionally joined to form an aromatic ring;
• and
• wherein at least one of the following is true:
• (i) one of A2, A3, or A4 is bonded to ring B, and the R3 bonded to A1 is selected from the group consisting of 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, partially or fully deuterated variants thereof, and combinations thereof;
• (ii) at least one of A5 to A8 is N;
• (iii) R4 is a 5-membered or 6-membered heterocycloalkyl ring;
• or
• (iv) A5 is N and the R2 bonded to A6 is selected from the group consisting of 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, partially or fully deuterated variants thereof, and combinations thereof.

A formulation comprising a compound having a formula M(LA)x(LB)y(LC)2:

• wherein the ligand LA is
• wherein the ligand LB is
• wherein the ligand LC is
• wherein M is a metal having an atomic number greater than 40;
• wherein x is 1, or 2;
• wherein y is 0, 1, or 2;
• wherein z is 0, 1, or 2;
• wherein x+y+z is the oxidation state of the metal M;
• wherein A1, A2, A3, A4, A5, A6, A7, and A8 are carbon or nitrogen;
• wherein ring B is bonded to ring A through a C—C bond;
• wherein M is bonded to ring A through a M-C bond;
• wherein X is selected from the group consisting of O, S, Se, CRR′, and NR1;
• wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
• wherein R3 represents mono, or di-substitution, or no substitution;
• wherein R2, RC, and RD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
• wherein R4 represents mono, di, tri, or tetra-substitution;
• wherein at least one R4 is a five-membered or six-membered heterocyclic ring which can be further substituted by RE;
• wherein RE represents mono, di, tri, or tetra-substitutions, or no substitutions;
• wherein each of R, R′, R1, R2, R3, R4, RC, RD, RX, RY, RZ and RE 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 any adjacent substituents of R, R′, RX, RY, and RZ are optionally joined to form a ring;
• and any two adjacent R1, R2, R3, R4, RC, RD, and RE are optionally joined to form an aromatic ring;
• and
• wherein at least one of the following is true:
• (i) one of A2, A3, or A4 is bonded to ring B, and the R3 bonded to A1 is selected from the group consisting of 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, partially or fully deuterated variants thereof, and combinations thereof;
• (ii) at least one of A5 to A8 is N;
• (iii) R4 is a 5-membered or 6-membered heterocycloalkyl ring;
• or
• (iv) A5 is N and the R2 bonded to A6 is selected from the group consisting of 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, partially or fully deuterated variants thereof, and combinations thereof.