Organic light-emitting device and display apparatus

1. An organic light-emitting device comprising:

a pair of electrodes; and

an organic compound layer disposed between the pair of electrodes,

wherein the organic compound layer includes an iridium complex represented by the following general formula [1] and a hydrocarbon compound represented by the following general formula [5]; and

the hydrocarbon compound comprises a compound formed only of an SP 2 carbon atom and a hydrogen atom:

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, 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 x comprises 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 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;

Ar 1 -(Ar 2 ) p —(Ar 3 ) q —Ar 1   [5]

in the formula [5]:

p and q each represent 0 or 1, and p+q is equal to or more than 1;

Ar 1 represents any one of substituents represented in the following substituent group α; and

Ar 2 and Ar 3 each represent any one of substituents represented in the following substituent group β, and Ar 2 and Ar 3 may be identical to or different from each other

[Substituent group α]

[Substituent group β]

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

3. The organic light-emitting device according to claim 1 , wherein the iridium complex is represented by the following formula [11]:

in the formula [11]:

R 61 to R 71 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;

t represents an integer of 1 to 3 and u represents an integer of 0 to 2, provided that t+u 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 1-position in the benzo[f]isoquinoline skeleton; and

the ring A comprises any one of structures represented by the following general formulae [12] to [16]:

in the formulae [12] to [16]:

R 72 to R 93 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 1-position in the benzo[f]isoquinoline skeleton.

4. The organic light-emitting device according to claim 3 , wherein the ring A comprises the structure represented by the general formula [12].

5. The organic light-emitting device according to claim 1 , wherein the iridium complex comprises an iridium complex represented by the following general formula [17]:

in the formula [17]:

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.

6. The organic light-emitting device according to claim 1 , wherein the organic compound layer is formed of the iridium complex, the hydrocarbon compound, and a third component.

7. The organic light-emitting device according to claim 6 , wherein a highest occupied molecular orbital (HOMO) level of the third component is larger in energy than a HOMO of the hydrocarbon compound.

8. The organic light-emitting device according to claim 6 , wherein a lowest unoccupied molecular orbital (LUMO) level of the third component is smaller in energy than a LUMO of the hydrocarbon compound.

9. A display apparatus comprising multiple pixels, wherein each pixel has the organic light-emitting device according to claim 1 and a transistor connected to the organic light-emitting device.

10. The display apparatus according to claim 9 , wherein the transistor includes an electrode formed of a transparent oxide semiconductor.

11. The display apparatus according to claim 9 , further comprising a color filter.

12. An imaging apparatus comprising:

a display portion, the display portion comprising the display apparatus according to claim 9 .

13. A lighting apparatus comprising:

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

an AC/DC converter.

14. An organic light-emitting device comprising:

a pair of electrodes; and

an organic compound layer disposed between the pair of electrodes,

wherein the organic compound layer includes an iridium complex represented by the following general formula [6] and a hydrocarbon compound represented by the following general formula [10]:

in the formula [6]:

R 31 to R 38 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;

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

a ring A represents a cyclic structure selected from a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene 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 1 comprises any one of structures represented by the following general formulae [7] to [9]:

in the formulae [7] to [9]:

R 39 to R 53 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;

Ar 5 —(Ar 6 ) r —(Ar 7 ) s —Ar 8   [10]

in the formula [10]:

r and s each represent 0 or 1, and r+s is equal to or more than 1;

Ar 5 represents any one of substituents represented in the following substituent group α′;

Ar 6 and Ar 7 each represent any one of substituents represented in the following substituent group β′, and Ar 6 and Ar 7 may be identical to or different from each other; and

Ar 8 represents any one of substituents represented in the following substituent group γ′

[Substituent group α′]

[Substituent group β′]

[Substituent group γ′]

 provided that the hydrocarbon represented by general formula [10] is not

15. The organic light-emitting device according to claim 14 , wherein the hydrocarbon compound is formed only of an SP 2 carbon atom and a hydrogen atom.

16. An organic light-emitting device according to claim 14 , wherein the iridium complex is represented by the following formula [11]:

in the formula [11]:

R 61 to R 71 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;

t represents an integer of 1 to 3 and u represents an integer of 0 to 2, provided that t+u 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 1-position in the benzo[f]isoquinoline skeleton; and

the ring A comprises any one of structures represented by the following general formulae [12] to [16]:

in the formulae [12] to [16]:

R 72 to R 93 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 1-position in the benzo[f]isoquinoline skeleton.

17. The organic light-emitting device according to claim 16 , wherein the ring A comprises the structure represented by the general formula [12].

18. The organic light-emitting device according to claim 14 , wherein the iridium complex comprises an iridium complex represented by the following general formula [17]:

in the formula [17]:

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.

19. The organic light-emitting device according to claim 14 , wherein the organic compound layer is formed of the iridium complex, the hydrocarbon compound, and a third component.

20. The organic light-emitting device according to claim 19 , wherein a highest occupied molecular orbital (HOMO) level of the third component is higher than an HOMO of the hydrocarbon compound.

21. The organic light-emitting device according to claim 19 , wherein a lowest unoccupied molecular orbital (LUMO) level of the third component is higher than an LUMO of the hydrocarbon compound.

22. A display apparatus, comprising multiple pixels, wherein each pixel has the organic light-emitting device according to claim 14 and a transistor connected to the organic light-emitting device.

23. The display apparatus according to claim 22 , wherein the transistor includes an electrode formed of a transparent oxide semiconductor.

24. A display apparatus according to claim 22 , further comprising a color filter.

25. An imaging apparatus comprising:

a display portion, the display portion comprising the display apparatus according to claim 22 .

26. A lighting apparatus comprising:

the organic light-emitting device according to claim 14 ; and

an AC/DC converter.