Organic light-emitting element and display apparatus

1. An organic light-emitting element comprising:

a pair of electrodes; and

an organic compound layer placed between the pair of electrodes,

wherein the organic compound layer comprising an iridium complex represented by the following general formula [1] and a metal complex compound represented by the following general formula [5]:

in the formula [1]:

R 1 to R 8 each represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group;

m represents an integer of 1 to 3 and n represents an integer of 0 to 2, provided that m+n equals 3;

ring A represents a cyclic structure selected from the group consisting of a benzene ring, a naphthalene ring, a phenanthrene ring, a fluorene ring, a 9,9-spirobifluorene ring and a chrysene ring, and is covalently bonded to the benzo[f]isoquinoline skeleton and Ir metal, and the ring A may further have a substituent;

X represents a bidentate ligand; and

a partial structure IrX n is selected from any one of structures represented by the following general formulae [2] to [4]:

in the formulae [2] to [4]:

R 10 to R 24 each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a cyano group, an aryloxy group, an aralkyl group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group, and when n represents 2, multiple substituents represented by any one of R 10 to R 24 may be identical to or different from each other;

ML 2   [5]

in the formula [5]:

M represents a divalent metal atom selected from the group consisting of beryllium, magnesium and zinc;

L represents a bidentate ligand; and

the partial structure ML comprises any one of the structures represented by the following general formulae [6] to [7]

in the formulae [6] to [7]:

R 30 to R 43 each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group.

2. The organic light-emitting element according to claim 1 , wherein R 30 to R 43 each represents a hydrogen atom, an alkyl group, or a phenyl group that may be substituted with an alkyl group.

3. The organic light-emitting element according to claim 1 , wherein m represents 2 and n represents 1.

4. The organic light-emitting element according to claim 1 , wherein the iridium complex represented by the general formula [1] comprises a compound represented by the following general formula [15]:

in the formula [15]:

R 80 to R 90 each represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group;

m represents an integer of 1 to 3 and n represents an integer of 0 to 2, provided that m+n equals 3;

*3 represents a bond between the ring A and the Ir metal, and *4 represents a bond between the ring A and a carbon atom at a 1-position in the benzo[f]isoquinoline skeleton; and

the ring A comprises any one of structures represented by the following general formulae [16] to [20]:

in the formulae [16] to [20]:

R 91 to R 112 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group; and

*3 represents a bonding position with the Ir metal and *4 represents a bonding position with the carbon atom at the 1-position in the benzo[f]isoquinoline skeleton.

5. The organic light-emitting element according to claim 4 , wherein the ring A comprises the structure represented by the general formula [16].

6. The organic light-emitting element according to claim 4 , wherein R 80 to R 90 , and R 91 to R 112 each represents a hydrogen atom, an alkyl group, or a phenyl group that may be substituted with an alkyl group.

7. The organic light-emitting element according to claim 1 , wherein the iridium complex represented by the general formula [1] comprises an iridium complex represented by the following general formula [21]:

in the formula [21]:

Q 1 to Q 9 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, or a cyano group; and

G represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, or a substituted or unsubstituted phenyl group.

8. The organic light-emitting element according to claim 7 , wherein Q 1 to Q 9 each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group that may be substituted with an alkyl group having 1 to 4 carbon atoms.

9. The organic light-emitting element according to claim 1 , wherein the organic compound layer comprises an emission layer including a host and a guest;

the guest comprises the iridium complex represented by the general formula [1]; and

the host comprises the metal complex compound represented by the general formula [5].

10. The organic light-emitting element according to claim 9 , wherein the organic compound layer further comprises an assist material different from the host and the guest.

11. The organic light-emitting element according to claim 10 , wherein the assist material comprises an iridium complex.

12. The organic light-emitting element according to claim 1 , wherein the organic light-emitting element emits red light.

13. The organic light-emitting element according to claim 1 , further comprising an active element connected to the organic light-emitting element.

14. The organic light-emitting element according to claim 1 , further comprising a substrate and other organic light-emitting elements on the substrate.

15. A display apparatus comprising multiple pixels, wherein each pixel has the organic light-emitting element according to claim 1 and an active element connected to the organic light-emitting element.

16. The display apparatus according to claim 15 , wherein an electrode of the active element is formed of a transparent oxide semiconductor.

17. A lighting apparatus comprising:

the organic light-emitting element according to claim 1 ; and

a circuit connected to the organic light-emitting element.

18. An image-forming apparatus comprising:

a photosensitive member;

charging unit for charging a surface of the photosensitive member;

exposing unit for exposing the photosensitive member to form an electrostatic latent image; and

developing unit for developing the electrostatic latent image formed on the surface of the photosensitive member,

wherein the exposing unit includes the organic light-emitting element according to claim 1 .

19. An ink comprising an iridium complex represented by the following general formula [1] and a metal complex compound represented by the following general formula [5]:

in the formula [1]:

R 1 to R 8 each represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group;

m represents an integer of 1 to 3 and n represents an integer of 0 to 2, provided that m+n equals 3;

ring A represents a cyclic structure selected from the group consisting of a benzene ring, a naphthalene ring, a phenanthrene ring, a fluorene ring, a 9,9-spirobifluorene ring and a chrysene ring, and is covalently bonded to a benzo[f]isoquinoline skeleton and an Ir metal, and the ring A may further have a substituent;

X represents a bidentate ligand; and

a partial structure IrX n is selected from any one of structures represented by the following general formulae [2] to [4]:

in the formulae [2] to [4]:

R 10 to R 24 each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aryloxy group, an aralkyl group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group, and when n represents 2, multiple substituents represented by any one of R 10 to R 24 may be identical to or different from each other;

ML 2   [5]

in the formula [5]:

M represents a divalent metal atom selected from the group consisting of beryllium, magnesium and zinc;

L represents a bidentate ligand; and

when M represents beryllium or magnesium, a partial structure ML comprises any one of structures represented by the following general formulae [6] to [7], and when M represents zinc, the partial structure ML comprises any one of the structures represented by the following general formulae [6] to [7]

in the formulae [6] to [7]:

R 30 to R 57 each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a substituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group.

20. The ink according to claim 19 , further comprising a solvent.