Organic light-emitting element

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 has an iridium complex represented by the following general formula [1] and a heterocycle-containing compound represented by the following general formula [5]:

in the formula [1]:

R 1 to R 8 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano 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;

a ring A represents a cyclic structure selected from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, and a 9,9-spirobifluorene 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 comprises any one of structures represented by the following general formulae [2] to [4]:

in the formulae [2] to [4]:

R 9 to R 23 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group,

in the formula [5]:

Z represents an oxygen atom or a sulfur atom;

a ring including Z is a five- or six-membered ring;

a ring B 1 and a ring B 2 each represent a cyclic structure selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a triphenylene ring, and a chrysene ring, and may be identical to or different from each other;

Y 1 and Y 2 each represent an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group;

a represents an integer of 0 to 4, and when a represents 2 or more, multiple Y 1 's may be identical to or different from each other;

b represents an integer of 0 to 4, provided that when the ring B 2 represents a benzene ring, b represents an integer of 0 to 3, and when b represents 2 or more, multiple Y 2 's may be identical to or different from each other;

Ar 1 represents a substituted or unsubstituted divalent aromatic hydrocarbon group;

Ar 2 represents a substituted or unsubstituted monovalent aromatic hydrocarbon group; and

p represents an integer of 0 to 4, and when p represents 2 or more, multiple Ar 1 's may be identical to or different from each other,

wherein when:

(a) both of B 1 and B 2 are benzene rings,

(b) Z is a sulfur atom, and

(c) the ring including Z is a five-membered ring, then

p is not 0, and

the Ar 1 is selected from the group consisting of a naphthalenediyl group, a phenanthrenediyl group, an anthracenediyl group, a benzo[a]anthracenediyl group, a fluorenediyl group, a benzo[a]fluorenediyl group, a benzo[b]fluorenediyl group, a benzo[c]fluorenediyl group, a dibenzo[a,c]fluorenediyl group, a dibenzo[b,h]fluorenediyl group, a dibenzo[c,g]fluorenediyl group, an acenaphthylenediyl group, a chrysenediyl group, a benzo[b]chrysenediyl group, a pyrenediyl group, a benzo[e]pyrenediyl group, a triphenylenediyl group, a benzo[a]triphenylenediyl group, a benzo[b]triphenylenediyl group, a picenediyl group, a fluoranthenediyl group, a benzo[a]fluoranthenediyl group, a benzo[b]fluoranthenediyl group, a benzo[j]fluoranthenediyl group, a benzo[k]fluoranthenediyl group, a perylenediyl group, and a naphthacenediyl group.

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

3. 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 [6]:

in the formula [6]:

R 24 to R 34 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano 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;

*1 represents a bond between the ring A and the Ir metal, and *2 represents a bond between the ring A and a carbon atom at a 4-position in the benzo[f]isoquinoline skeleton; and

the ring A comprises any one of structures represented by the following general formulae [7] to [11]:

in the formulae [7] to [11]:

R 35 to R 56 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heteroaromatic group; and

*1 represents a bonding position with the Ir metal and *2 represents a bonding position with the carbon atom at the 4-position in the benzo[f]isoquinoline skeleton.

4. The organic light-emitting element according to claim 3 , wherein the ring A comprises the structure represented by the general formula [7].

5. The organic light-emitting element according to claim 1 , wherein in the heterocycle-containing compound represented by the general formula [5], a heterocycle formed of Z, the ring B 1 , and the ring B 2 comprises any one of heterocycles represented by the following general formulae [12] to [19]:

in the formulae [12] to [19], Z represents an oxygen atom or a sulfur atom.

6. 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 [20]:

in the formula [20]:

Q 1 to Q 9 each represent 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.

7. The organic light-emitting element according to claim 1 , wherein the heterocycle-containing compound represented by the general formula [5] comprises a dibenzothiophene compound represented by the following general formula [21]:

in the formula [21], E 1 to E 3 each represent a hydrogen atom, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.

8. The organic light-emitting element according to claim 7 wherein in the heterocycle-containing compounds represented by the general formulae [21] to [25]:

the p represents 1;

the Ar 1 represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthalenediyl group, a substituted or unsubstituted fluorenediyl group, a substituted or unsubstituted phenanthrenediyl group, a substituted or unsubstituted chrysenediyl group, or a substituted or unsubstituted triphenylenediyl group; and

the Ar 2 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted chrysenyl group, or a substituted or unsubstituted triphenylenyl group.

9. The organic light-emitting element according to claim 1 , wherein the heterocycle-containing compound represented by the general formula [5] comprises a benzonaphthothiophene compound represented by the following general formula [22]:

in the formula [22], E 4 to E 7 each represent a hydrogen atom, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.

10. The organic light-emitting element according to claim 1 , wherein the heterocycle-containing compound represented by the general formula [5] comprises a benzophenanthrothiophene compound represented by the following general formula [23]:

in the formula [23], E 8 to E 10 each represent a hydrogen atom, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.

11. The organic light-emitting element according to claim 1 , wherein the heterocycle-containing compound represented by the general formula [5] comprises a dibenzoxanthene compound represented by the following general formula [24]:

in the formula [24], E 11 to E 16 each represent a hydrogen atom, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.

12. The organic light-emitting element according to claim 1 , wherein the heterocycle-containing compound represented by the general formula [5] comprises a dibenzoxanthene compound represented by the following general formula [25]:

in the formula [25], E 17 to E 22 each represent a hydrogen atom, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.

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

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

the host comprises the heterocycle-containing compound represented by the general formula [5].

14. The organic light-emitting element according to claim 13 , wherein the organic compound layer further includes an assist material different from the host and the guest.

15. The organic light-emitting element according to claim 14 , wherein the assist material comprises an iridium complex.

16. 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.

17. An information processing apparatus comprising:

a display portion for displaying an image; and

an input portion for inputting image information,

wherein the display portion comprises the display apparatus according to claim 16 .

18. A lighting apparatus comprising:

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

an AC/DC converter circuit connected to the organic light-emitting element.

19. An image-forming apparatus comprising:

a photosensitive member;

a charging unit for charging a surface of the photosensitive member;

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

a 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 .

20. An exposing apparatus for exposing a photosensitive member comprising a plurality of the organic light-emitting elements according to claim 1 , wherein the organic light-emitting elements are placed to form a line along a predetermined direction.