Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir

A compound, having the structure:

• wherein
• M is a metal having an atomic weight greater than 40;
• (C—N) is a substituted or unsubstituted cyclometallated ligand;
• each of R8 and R11 to R14 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
• Z is selected from —CH2, —CRR, —NH, —NR, —O, —S, and —SiR;
• optionally, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with substituent R or CN;
• X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, CO2R, C(O)R, NR2, NO2, OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
• n has a value of at least 1;
• and
• m+n is the maximum number of ligands that may be attached to the metal.

An organic light emitting device, comprising:

• an anode;
• a cathode;
• and
• an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having the structure
• wherein
• M is a metal having an atomic weight greater than 40;
• (C—N) is a substituted or unsubstituted cyclometallated ligand, and (C—N) is different from at least one other ligand attached to the metal;
• each of R8 to R14 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group, wherein at least one of R8 to R14 is phenyl or substituted phenyl, and/or at least two of R8 to R14 that are adjacent are part of a fluorenyl group;
• n has a value of at least 1, wherein, when n is 3, none of R8 to R14 is a cyano group;
• and
• m+n is the maximum number of ligands that may be attached to the metal;
• and,
• optionally, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with substituent R.

An organic light emitting device, comprising:

• an anode;
• a cathode;
• and
• an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having the structure:
• wherein
• M is a metal having an atomic weight greater than 40;
• each of R8 to R14 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group, wherein at least one of R8 to R14 is phenyl or substituted phenyl, and/or at least two of R8 to R14 that are adjacent are part of a fluorenyl group;
• and,
• optionally, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with substituent R and CN.

An organic light emitting device, comprising:

• an anode;
• a cathode;
• and
• an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having a ligand with the structure:
• wherein
• each R is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group, wherein at least one of R8 to R14 is phenyl or substituted phenyl, and/or at least two of R8 to R14 that are adjacent are part of a fluorenyl group;
• and
• optionally, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with substituent R.