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 of Formula R1R2R3M-L-M′;
• wherein
• M is Si or Ge;
• L is selected from the group consisting of a direct bond, or selected from the group consisting of O, S, Se, BR, BRR′, PR, CR, NR, C═O, C═S, C═NR, C═CRR′, CRR′, SO, SO2, SiRR′, GeRR′, and P(O)R;
• when L is a direct bond, M′ is SiR4R5R6 or GeR4R5R6;
• when L is not a direct bond, M′ is SiR4R5R6, GeR4R5R6, or one or more hydrocarbon groups provided that at least one of the one or more hydrocarbon groups is a carbocyclic group;
• each R1, R2, R3, R4, R5, and R6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, boryl, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
• any two substituents can be joined or fused to form a ring;
• at least one of R1, R2, and R3 comprises a structure selected from the group consisting of triphenylene, tetraphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, dibenzofluorene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), indolocarbazole, indolodibenzothiophene, indolodibenzofuran, indodibenzoselenophene, indolodibenzofluorene, naphthalene, boryl, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazole, benzimidazole, and aza variants thereof;
• with the proviso that:
• if L is a direct bond, and both M and M′ comprise Si, then at least one of R1, R2, and R3 comprises benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim) or boryl, or R1, R2, and R3 collectively comprise two structures selected from the group consisting of triphenylene, tetraphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, dibenzofluorene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), indolocarbazole, indolodibenzothiophene, indolodibenzofuran, indodibenzoselenophene, indolodibenzofluorene, naphthalene, boryl, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazole, benzimidazole, and aza variants thereof, with the additional proviso that the same R1, R2, and R3 does not comprise a bicarbazole;
• if M is Si, then at least two of R1, R2, and R3 are a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings, which can be further substituted;
• if M′ is SiR4R5R6, then at least two of R4, R5, and R6 are a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings, which can be further substituted;
• and
• the compound does not comprise a non-ring N atom.

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 of Formula R1R2R3M-L-M′;
• wherein
• M is Si or Ge;
• L is selected from the group consisting of a direct bond, or selected from the group consisting of O, S, Se, BR, BRR′, PR, CR, NR, C═O, C═S, C═NR, C═CRR′, CRR′, SO, SO2, SiRR′, GeRR′, and P(O)R;
• when L is a direct bond, M′ is SiR4R5R6 or GeR4R5R6;
• when L is not a direct bond, M′ is SiR4R5R6, GeR4R5R6, or one or more hydrocarbon groups provided that at least one of the one or more hydrocarbon groups is a carbocyclic group;
• each R1, R2, R3, R4, R5, and R6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, boryl, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfonyl, sulfonyl, phosphino, selenyl, and combinations thereof;
• any two substituents can be joined or fused to form a ring;
• at least one of R1, R2, and R3 comprises a structure selected from the group consisting of triphenylene, tetraphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, dibenzofluorene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), indolocarbazole, indolodibenzothiophene, indolodibenzofuran, indodibenzoselenophene, indolodibenzofluorene, naphthalene, boryl, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazole, benzimidazole, and aza variants thereof;
• with the proviso that:
• if L is a direct bond, and both M and M′ comprise Si, then at least one of R1, R2, and R3 comprises benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim) or boryl, or R1, R2, and R3 collectively comprise two structures selected from the group consisting of triphenylene, tetraphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, dibenzofluorene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), indolocarbazole, indolodibenzothiophene, indolodibenzofuran, indodibenzoselenophene, indolodibenzofluorene, naphthalene, boryl, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazole, benzimidazole, and aza variants thereof, with the additional proviso that the same R1, R2, and R3 does not comprise a bicarbazole;
• if M is Si, then at least two of R1, R2, and R3 are a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings, which can be further substituted;
• if M′ is SiR4R5R6, then at least two of R4, R5, and R6 are a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings, which can be further substituted;
• and
• the compound does not comprise a non-ring N atom.