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 of formula (I)
• wherein
• M is a metal;
• ring B is a one of the following carbene ligands:
• wherein
• each X25 to X28 independently represents N or C;
• R3 represents mono to the maximum allowable substitution;
• each occurrence of R1 to R3 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof;
• wherein any two adjacent R1 to R3 are optionally joined or fused together to form a ring which is optionally substituted;
• and
• the dashed line inside the five-member ring represents zero or one double-bond;
• R represents mono to the maximum allowable substitution;
• each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof;
• wherein any two adjacent R are optionally joined or fused together to form a ring which is optionally substituted;
• provided that ring B is not
• and
• provided that when ring B is
• then R1 is not aryl substituted with aryl;
• ring A is an amide ligand selected from the group consisting of formula (Ai) and formula (Aii);
• wherein, in formula (Ai),
• the dashed line represents coordination to M;
• each X5, X6, X7, and X8 independently represents N or C;
• RA represents mono to the maximum allowable substitution;
• wherein at least one pair atoms selected from the group consisting of X5 and X6, X6 and X7, and X7 and X8 each represent C, wherein the respective adjacent groups RA together form a fused ring having the following formula:
• wherein each X1, X2, X3, and X4 independently represents N or C;
• n is 0 or 1;
• wherein when n is 0, then X3 binds directly to formula (Ai);
• RB represents mono to the maximum allowable substitution;
• each occurrence of RA and RB is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof;
• wherein at least two adjacent X1 to X4 represent C, wherein the respective adjacent RB are joined or fused together to form an aryl or heteroaryl ring, wherein the aryl or heteroaryl ring is optionally substituted and optionally comprises additional ring fusions;
• wherein any two adjacent RA are optionally joined or fused together to form a ring which is optionally substituted;
• wherein, in formula (Aii);
• each X11 to X18 independently represents N or C;
• RA and RB each represent mono to the maximum allowable substitution;
• and
• each occurrence of RA and RB is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof;
• wherein any two adjacent RA and RB are optionally joined or fused together to form a ring which is optionally substituted.

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 of formula (I):
• wherein
• M is a metal;
• ring B is one of the following carbene ligands:
• wherein
• each X25 to X28 independently represents N or C;
• R3 represents mono to the maximum allowable substitution;
• each occurrence of R1 to R3 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof;
• wherein any two adjacent R1 to R3 are optionally joined or fused together to form a ring which is optionally substituted;
• and
• the dashed line inside the five-member ring represents zero or one double-bond;
• R represents mono to the maximum allowable substitution;
• each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof;
• wherein any two adjacent R are optionally joined or fused together to form a ring which is optionally substituted;
• provided that ring B is not
• and
• provided that when ring B is
• then R1 is not aryl substituted with aryl;
• ring A is an amide ligand selected from the group consisting of formula (Ai) and formula (Aii);
• wherein, in formula (Ai),
• the dashed line represents coordination to M;
• each X5, X6, X7, and X8 independently represents N or C;
• RA represents mono to the maximum allowable substitution;
• wherein at least one pair atoms selected from the group consisting of X5 and X6, X6 and X7, and X7 and X8 each represent C, wherein the respective adjacent groups RA together form a fused ring having the following formula:
• wherein each X1, X2, X3, and X4 independently represents N or C;
• n is 0 or 1;
• wherein when n is 0, then X3 binds directly to formula (Ai);
• RB represents mono to the maximum allowable substitution;
• each occurrence of RA and RB is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof;
• wherein at least two adjacent X1 to X4 represent C, wherein the respective adjacent RB are joined or fused together to form an aryl or heteroaryl ring, wherein the aryl or heteroaryl ring is optionally substituted and optionally comprises additional ring fusions;
• wherein any two adjacent RA are optionally joined or fused together to form a ring which is optionally substituted;
• wherein, in formula (Aii);
• each X11 to X18 independently represents N or C;
• RA and RB each represent mono to the maximum allowable substitution;
• and
• each occurrence of RA and RB is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof;
• wherein any two adjacent RA and RB are optionally joined or fused together to form a ring which is optionally substituted.