Iridium complex compound, process for producing the compound, composition including the compound, organic electroluminescent element, display device, and illuminator

1. An iridium complex compound represented by the following formula (1):

Ir(L 1 ) m (L 2 ) n (L 3 ) 3-m-n   (1)

wherein in formula (1):

Ir represents an iridium atom;

L 1 to L 3 each independently represent an organic ligand bonded to the Ir, and the L 1 is selected from the group consisting of ligands represented by any of the following formula (2-1) to formula (2-3) or is a ligand represented by any of formula (2-1) to formula (2-3) which includes a partial structure represented by the following formula (4) and the L 2 is a ligand represented by the following formula (3-1) or is a ligand represented by formula (3-1) which includes a partial structure represented by the following formula (4);

m and n each are an integer of 1 or 2, and m+n is 3 or less;

the L 3 is not a ligand represented by any of formulae (2-1) to (2-3) or by formula (3-1); and

in the case where there are a plurality of moieties represented by any of L 1 to L 3 , these moieties may be the same or different:

wherein

X 1 and X 2 each independently represent a nitrogen atom or C—R 21 ; and R 1 to R 21 and R 31 to R 38 each independently represent a hydrogen atom, an alkyl group having 1-20 carbon atoms, a (hetero)aralkyl group having 7-40 carbon atoms, an alkoxy group having 1-20 carbon atoms, a (hetero)aryloxy group having 3-20 carbon atoms, an alkylsilyl group in which each alkyl group has 1-20 carbon atoms, a (hetero)arylsilyl group in which each aryl group has 6-20 carbon atoms, an alkylcarbonyl group having 2-20 carbon atoms, an arylcarbonyl group having 7-20 carbon atoms, an alkylamino group having 1-20 carbon atoms, a (hetero)arylamino group having 6-20 carbon atoms, or a (hetero)aryl group having 3-30 carbon atoms, and these groups may further have substituents,

R 1 to R 4 and R 31 to R 34 each may be bonded to any adjacent one of the R 1 to R 4 or of the R 31 to R 34 to form a ring, and the ring may further have one or more substituents,

X 3 represents an oxygen atom, a sulfur atom, or N—R 39 , and R 39 represents an alkyl group having 1-20 carbon atoms, a (hetero)aralkyl group having 7-40 carbon atoms, or a (hetero)aryl group having 3-20 carbon atoms;

wherein at least one of L 1 to L 3 in the formula (1) includes at least one partial structure represented by the following formula (4):

—Ar 1 —Z  (4)

wherein Ar 1 1 represents an arylene group having 6-20 carbon atoms, and Z represents an alkyl group having 5-20 carbon atoms, a (hetero)aralkyl group having 7-40 carbon atoms, an alkoxy group having 4-20 carbon atoms, a (hetero)aryloxy group having 3-20 carbon atoms, or a substituent represented by the following formula (4-1):

wherein R 41 to R 44 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1-20 carbon atoms, a (hetero)aralkyl group having 7-40 carbon atoms, an alkoxy group having 1-20 carbon atoms, a (hetero)aryloxy group having 3-20 carbon atoms, or a (hetero)aryl group having 3-20 carbon atoms; R 45 to R 49 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1-20 carbon atoms, a (hetero)aralkyl group having 7-40 carbon atoms, an alkoxy group having 1-20 carbon atoms, or a (hetero)aryloxy group having 3-20 carbon atoms; and p represents an integer of 1 to 4, and when p is 2 or larger, the multiple R 41 moieties to R 44 moieties each may be the same or different.

2. The iridium complex compound according to claim 1 , wherein n in the formula (1) is 2.

3. The iridium complex compound according to claim 1 , wherein X 3 in the formula (3-1) is a sulfur atom.

4. The iridium complex compound according to claim 1 , wherein X 1 and X 2 in the formula (2-1) and the formula (2-2) are each a nitrogen atom.

5. The iridium complex compound according to claim 1 , wherein L 2 , which is represented by the formula (3-1), includes the partial structure represented by the formula (4-1).

6. The iridium complex compound according to claim 1 , wherein R 1 to R 21 and R 31 to R 38 in the formulae (2-1) to (2-3) and the formula (3-1) each independently are a hydrogen atom, an alkyl group having 1-4 carbon atoms, an aryl group having 6-18 carbon atoms (the aryl group being not an aralkyl-substituted phenyl group), a phenyl group substituted with one or more aralkyl groups having 7-16 carbon atoms, or an arylamino group having 6-15 carbon atoms, or are bonded to any adjacent one of the R 1 to R 21 or of the R 31 to R 34 to form an aromatic heterocyclic group.

7. The iridium complex compound according to claim 1 , wherein at least two of R 1 to R 9 in the formula (2-1), at least two of R 1 to R 4 and R 10 to R 14 in the formula (2-2), and at least two of R 1 to R 4 and R 16 to R 20 in the formula (2-3) are a group other that a hydrogen atom, and at least one of R 31 to R 38 in the formula (3-1) is a group other than a hydrogen atom.

8. The iridium complex compound according to claim 7 , wherein at least one of the groups other than a hydrogen atom is a phenyl group substituted with one or more aralkyl groups having 7-16 carbon atoms.

9. The iridium complex compound according to claim 1 , wherein R 3 in the formulae (2-1) to (2-3) or R 33 in the formula (3-1) includes the substituent represented by the formula (4).

10. A process for producing the iridium complex compound according to claim 1 , comprising:

reacting an iridium complex compound represented by the following formula (5) with a compound corresponding to a ligand represented by the formula (3-1) or

reacting an iridium complex compound represented by the following formula (6) with a compound corresponding to a ligand represented by any of the formulae (2-1) to (2-3),

in the presence of a sliver salt:

wherein L 1 and L 2 respectively represent the same ligands as the L 1 and L 2 in the formula (1), and L 41 and L 42 represent an organic ligand, with the proviso that L 41 is not a ligand represented by the formula (3-1) and L 42 is not a ligand represented by any of the formulae (2-1) to (2-3).

11. The process for production according to claim 10 , wherein L 41 and L 42 in the formula (5) and the formula (6) are represented by the following formula (7-1) or formula (7-2):

wherein R 50 to R 56 each independently represent a hydrogen atom, an alkyl group which has 1-20 carbon atoms and may have been substituted with one or more fluorine atoms, a phenyl group which may have been substituted with one or more alkyl groups having 1-20 carbon atoms, or a halogen atom.

12. A composition which comprises the iridium complex compound according to claim 1 and a solvent.

13. An organic electroluminescent element which comprises an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein at least one of the organic layers comprises the iridium complex compound according to claim 1 .

14. A display device which employs the organic electroluminescent element according to claim 13 .

15. An illuminator which employs the organic electroluminescent element according to claim 13 .