Iridium complex compound, organic electroluminescent element material, organic electroluminescent element, illumination device and display device

An iridium complex compound represented by a following general formula (2):

• [wherein in the general formula (2), Ar represents an aromatic hydrocarbon ring, an aromatic heterocyclic ring, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic ring;
• independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of each other, Ra and Rc represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]

An iridium complex compound represented by a following general formula (3):

• [wherein in the general formula (3), independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of one another, Ra, Rc and Ra3 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2;
• nR3 represents an integer of 1 to 5;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]

An organic electroluminescent element material represented by a following general formula (1):

• [wherein in the general formula (1), each of a ring Am, a ring An, a ring Bm and a ring Bn represents a five-membered or six-membered aromatic hydrocarbon ring or aromatic heterocyclic ring;
• Ar represents an aromatic hydrocarbon ring, an aromatic heterocyclic ring, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic ring;
• independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of one another, each of Ra, Rb and Rc represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2, and nb represents an integer of 1 to 4;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• and note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]

An organic electroluminescent element material represented by a following general formula (2):

• [wherein in the general formula (2), Ar represents an aromatic hydrocarbon ring, an aromatic heterocyclic ring, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic ring;
• independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of each other, Ra and Rc represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]

An organic electroluminescent element material represented by a following general formula (3):

• [wherein in the general formula (3), independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of one another, Ra, Rc and Ra3 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2;
• nR3 represents an integer of 1 to 5;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]

An organic electroluminescent element in which at least one organic layer including a light emitting layer is sandwiched between an anode and a cathode,

• wherein the at least one organic layer comprises an iridium complex compound represented by a following general formula (1):
• [wherein in the general formula (1), each of a ring Am, a ring An, a ring Bm and a ring Bn represents a five-membered or six-membered aromatic hydrocarbon ring or aromatic heterocyclic ring;
• Ar represents an aromatic hydrocarbon ring, an aromatic heterocyclic ring, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic ring;
• independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of one another, each of Ra, Rb and Rc represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2, and nb represents an integer of 1 to 4;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• and note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]

An organic electroluminescent element in which at least one organic layer including a light emitting layer is sandwiched between an anode and a cathode,

• wherein the at least one organic layer comprises an iridium complex compound represented by a following general formula (2):
• [wherein in the general formula (2), Ar represents an aromatic hydrocarbon ring, an aromatic heterocyclic ring, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic ring;
• independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of each other, Ra and Rc represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]

An organic electroluminescent element in which at least one organic layer including a light emitting layer is sandwiched between an anode and a cathode,

• wherein the at least one organic layer comprises an iridium complex compound represented by a following general formula (3):
• [wherein in the general formula (3), independently of one another, each of R1m, R2m, R1n and R2n represents an alkyl group with a carbon number of 2 or more, an aromatic hydrocarbon ring group, an aromatic heterocyclic ring group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and moreover, may have a substituent;
• independently of one another, Ra, Rc and Ra3 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, the non-aromatic hydrocarbon ring group or the non-aromatic heterocyclic ring group, and may further have a substituent;
• each of na and nc represents 1 or 2;
• nR3 represents an integer of 1 to 5;
• m represents 1 or 2, n represents 1 or 2, and m+n is 3;
• note that a state where structures of three ligands arranged in Ir are entirely same does not occur.]