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,
• wherein the organic layer comprises a compound comprising a ligand LA comprising structures of both Formula I and Formula II:
• wherein:
• 1) Ring A or ring B of Formula I is fused with Formula II where indicated by the wavy lines to form a fused ring E;
• 2) Ring A or ring B of Formula I is fused to form a fused aromatic structure which is further fused with Formula II where indicated by the wavy lines to form a fused ring E;
• or
• 3) ring A or ring B forms a direct bond to an aromatic group which is fused with Formula II where indicated by the wavy lines to form a fused ring E,
• wherein:
• ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
• Z1 is carbene carbon or N;
• Z2 is C;
• K1 and K2 are each independently a direct bond, O, or S with at least one of them being a direct bond;
• R2 and R3 each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
• and
• RE independently represents mono, di, or up to the maximum allowed number of substitutions to its associated ring;
• each R2 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;
• each R3 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
• RE for each occurrence 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,
• n is 1 or 2,
• at least one of RE is an alkyl, cycloalkyl, aryl or heteroaryl;
• ring E has at least one ring carbon with two different RE substituents, wherein one of the RE substituents is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, arylalkyl, amino, silyl, alkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof, and the other RE substituent is selected from the group consisting of cycloalkyl, aryl, and heteroaryl;
• if condition 1) or condition 2) is true, then at least one RE that is adjacent to the wavy lines of Formula II is hydrogen or deuterium;
• if condition 1) is true and Formula II fuses to ring B, then at least one RE is a cyclic substituent;
• and
• if condition 1) or condition 2) is true and Formula II fuses to ring A,
• then n is 1;
• wherein two adjacent substituents can be joined or fused together to form a ring;
• wherein the ligand LA is coordinated to Ir through the two dashed lines;
• wherein Ir is coordinated to a second ligand;
• wherein the ligand LA can be linked with the other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
• wherein the second ligand is a bidentate ligand that is different from LA;
• wherein the second ligand is:
• i) a substituted or unsubstituted acetylacetonate ligand;
• or
• ii) a ligand having a first aromatic moiety having a first coordinating atom, wherein the first aromatic moiety is bonded to a second aromatic moiety having a second coordinating atom, wherein the rings of the first and second aromatic moieties that include the first and second coordinating atoms, respectively, are a substituted or unsubstituted 5-membered or 6-membered aryl or heteroaryl ring;
• wherein if the second ligand is option ii) and comprises deuterium, the deuterium is not directly bonded to the rings of the first and second aromatic moieties containing the first and second coordinating atoms, respectively;
• and
• if condition 3) is true and the aromatic group is a 6-membered ring, then Formula II fuses to the ring atoms of said 6-membered ring that are para and meta to the ring atom that bonds to ring A or ring B.

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,
• wherein the organic layer comprises a compound comprising a ligand LA comprising structures of both Formula I and Formula II:
• wherein:
• 1) Ring A or ring B of Formula I is fused with Formula II where indicated by the wavy lines to form a fused ring E;
• 2) Ring A or ring B of Formula I is fused to form a fused aromatic structure which is further fused with Formula II where indicated by the wavy lines to form a fused ring E;
• or
• 3) ring A or ring B forms a direct bond to an aromatic group which is fused with Formula II where indicated by the wavy lines to form a fused ring E,
• wherein:
• ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
• Z1 is carbene carbon or N;
• Z2 is C;
• K1 and K2 are each independently a direct bond, O, or S with at least one of them being a direct bond;
• R2 and R3 each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
• and
• RE independently represents mono, di, or up to the maximum allowed number of substitutions to its associated ring;
• each R2 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;
• each R3 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, germyl boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
• RE for each occurrence 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,
• n is 1 or 2,
• at least one of RE is an alkyl, cycloalkyl, aryl or heteroaryl;
• ring E has at least one ring carbon with two different RE substituents, wherein one of the RE substituents is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, arylalkyl, amino, silyl, alkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof, and the other RE substituent is selected from the group consisting of cycloalkyl, aryl, and heteroaryl;
• if condition 1) or condition 2) is true, then at least one RE that is adjacent to the wavy lines of Formula II is hydrogen or deuterium;
• if condition 1) is true and Formula II fuses to ring B, then at least one RE is a cyclic substituent;
• and
• if condition 1) or condition 2) is true and Formula II fuses to ring A,
• then n is 1;
• wherein two adjacent substituents can be joined or fused together to form a ring;
• wherein the ligand LA is coordinated to Ir through the two dashed lines;
• wherein Ir is coordinated to a second ligand;
• wherein the ligand LA can be linked with the other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
• wherein the second ligand is a bidentate ligand that is different from LA;
• wherein the second ligand is:
• i) a substituted or unsubstituted acetylacetonate ligand;
• or
• ii) a ligand having a first aromatic moiety having a first coordinating atom, wherein the first aromatic moiety is bonded to a second aromatic moiety having a second coordinating atom, wherein the rings of the first and second aromatic moieties that include the first and second coordinating atoms, respectively, are a substituted or unsubstituted 5-membered or 6-membered aryl or heteroaryl ring;
• wherein if the second ligand is option ii) and comprises deuterium, the deuterium is not directly bonded to the rings of the first and second aromatic moieties containing the first and second coordinating atoms, respectively;
• and
• if condition 3) is true and the aromatic group is a 6-membered ring, then Formula II fuses to the ring atoms of said 6-membered ring that are para and meta to the ring atom that bonds to ring A or ring B.