Iridium complex compound, and composition, organic electroluminescent element, display device, and lighting device each containing the compound

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

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

wherein:

Ir represents an iridium atom;

L 1 to L 3 each represent an organic ligand and are bonded to the Ir;

m is an integer of 1 to 2;

n is an integer of 1 to 2, m+n being 3;

if at least one of L 1 to L 3 is present in plural number, these may be the same or different;

at least one partial structure represented by formula (2) is present in at least one of L 1 to L 3 :

Ar 1 —X  (2);

L 1 represents a ligand represented by formula (3-1) or (3-2);

R 1 to R 5 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, an alkylsilyl group in which the alkyl group has 1-20 carbon atoms, an arylsilyl group in which the 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 2-20 carbon atoms, an arylamino group having 6-20 carbon atoms, or a (hetero)aryl group having 3-12 ring carbon atoms, wherein the heteroaryl ring does not include a phosphorus atom; the groups may be further substituted with at least one group selected from the group consisting of 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, an alkylsilyl group in which the alkyl group has 1-20 carbon atoms, an arylsilyl group in which the 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 2-20 carbon atoms, an arylamino group having 6-20 carbon atoms, and a (hetero)aryl group having 3-20 carbon atoms;

R 8 to R 11 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1-20 carbon atoms, an alkoxy group having 1-20 carbon atoms, a (hetero)aryloxy group having 3-20 carbon atoms, an alkylsilyl group in which the alkyl group has 1-20 carbon atoms, an arylsilyl group in which the aryl group has 6-20 carbon atoms, an alkylcarbonyl group having 2-20 carbon atoms, or an alkylamino group having 2-20 carbon atoms, such that the groups may be further substituted with at least one group selected from the group consisting of 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, an alkylsilyl group in which the alkyl group has 1-20 carbon atoms, an arylsilyl group in which the 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 2-20 carbon atoms, an arylamino group having 6-20 carbon atoms, and a (hetero)aryl group having 3-20 carbon atoms;

L 2 in formula (1) comprises at least one of the partial structure represented by the formula (2);

Ar 1 represents a phenyl group;

in at least one of the partial structure represented by formula (2), X represents an alkyl group substituted with an aryl group having 7-40 carbon atoms;

L 2 in formula (1) is a ligand represented by the following formula (4-1):

R 12 to R 19 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, such that the groups may be further substituted with at least one group selected from the group consisting of 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, an alkylsilyl group in which the alkyl group has 1-20 carbon atoms, an arylsilyl group in which the 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 2-20 carbon atoms, and a (hetero)aryl group having 3-20 carbon atoms; and

the R 12 to R 15 each may be bonded to any adjacent one of the R 12 to R 15 and the R 16 to R 19 each may be bonded to any adjacent one of the R 16 to R 19 , through an alkylene group having 3-12 carbon atoms or alkenylene group having 3-12 carbon atoms to form a ring; the R 15 and the R 16 may be bonded to each other through an alkylene group having 3-12 carbon atoms or alkenylene group having 3-12 carbon atoms to form a ring, such that these rings may be substituted with at least one group selected from the group consisting of 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, an alkylsilyl group in which the alkyl group has 1-20 carbon atoms, an arylsilyl group in which the 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 2-20 carbon atoms, and a (hetero)aryl group having 3-20 carbon atoms; and

R 17 includes the partial structure represented by formula (2).

2. The iridium complex compound according to claim 1 , wherein the R 1 represents a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted (hetero)aralkyl group having 7-40 carbon atoms, a substituted or unsubstituted alkylamino group having 2-20 carbon atoms, a substituted or unsubstituted arylamino group having 6-20 carbon atoms, or a substituted or unsubstituted (hetero)aryl group having 3-12 ring carbon atoms, wherein the heteroaryl ring does not include a phosphorus atom.

3. The iridium complex compound according to claim 1 , wherein the R 5 represents a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted (hetero)aralkyl group having 7-40 carbon atoms, a substituted or unsubstituted alkylamino group having 2-20 carbon atoms, a substituted or unsubstituted arylamino group having 6-20 carbon atoms, or a substituted or unsubstituted(hetero)aryl group having 3-12 ring carbon atoms, wherein the heteroaryl ring does not include a phosphorus atom.

4. A composition, comprising the iridium complex compound of claim 1 and a solvent.

5. The iridium complex according to claim 1 , wherein L 1 represents a ligand represented by formula (3-1).

6. The iridium complex compound according to claim 5 , wherein the R 1 represents a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted (hetero)aralkyl group having 7-40 carbon atoms, a substituted or unsubstituted alkylamino group having 2-20 carbon atoms, a substituted or unsubstituted arylamino group having 6-20 carbon atoms, or a substituted or unsubstituted (hetero)aryl group having 3-12 ring carbon atoms, wherein the heteroaryl ring does not include a phosphorus atom.

7. The iridium complex compound according to claim 5 , wherein the R 5 represents a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted (hetero)aralkyl group having 7-40 carbon atoms, a substituted or unsubstituted alkylamino group having 2-20 carbon atoms, a substituted or unsubstituted arylamino group having 6-20 carbon atoms, or a substituted or unsubstituted(hetero)aryl group having 3-12 ring carbon atoms, wherein the heteroaryl ring does not include a phosphorus atom.

8. The iridium complex according to claim 1 , wherein L 1 represents a ligand represented by formula (3-2).

9. The iridium complex compound according to claim 8 , wherein the R 1 represents a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted (hetero)aralkyl group having 7-40 carbon atoms, a substituted or unsubstituted alkylamino group having 2-20 carbon atoms, a substituted or unsubstituted arylamino group having 6-20 carbon atoms, or a substituted or unsubstituted (hetero)aryl group having 3-12 ring carbon atoms, wherein the heteroaryl ring does not include a phosphorus atom.

10. The iridium complex compound according to claim 8 , wherein the R 5 represents a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted (hetero)aralkyl group having 7-40 carbon atoms, a substituted or unsubstituted alkylamino group having 2-20 carbon atoms, a substituted or unsubstituted arylamino group having 6-20 carbon atoms, or a substituted or unsubstituted(hetero)aryl group having 3-12 ring carbon atoms, wherein the heteroaryl ring does not include a phosphorus atom.

11. An organic electroluminescent element, comprising:

an anode;

a cathode; and

at least one organic layer disposed between the anode and the cathode,

wherein at least one of the organic layer comprises the iridium complex compound of claim 1 .

12. The organic electroluminescent element according to claim 11 , wherein the organic layer comprising the iridium complex compound is a layer formed using a composition comprising the iridium complex compound.

13. A display device, comprising the organic electroluminescent element according to claim 11 .

14. A lighting device, comprising the organic electroluminescent element according to claim 11 .