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 carbene ligand;
• 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;
• ring A is an amide ligand selected from the group consisting of formula (A-1) and formula (A-2);
• wherein, in formula (A-1),
• the dashed line represents coordination to M;
• each X3, X6, X7, and X8 independently represents N or C;
• RA represents mono to the maximum allowable substitution;
• wherein any two adjacent groups RA may optionally 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 (A-1);
• 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 any two RB are optionally joined or fused together to form a ring which is optionally substituted;
• wherein, in formula (A-2);
• 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, 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 a carbene ligand;
• 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;
• ring A is an amide ligand selected from the group consisting of formula (A-1) and formula (A-2);
• wherein, in formula (A-1),
• the dashed line represents coordination to M;
• each X3, X6, X7, and X8 independently represents N or C;
• RA represents mono to the maximum allowable substitution;
• wherein any two adjacent groups RA may optionally 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 (A-1);
• 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 any two RB are optionally joined or fused together to form a ring which is optionally substituted;
• wherein, in formula (A-2);
• 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, 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.