Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
A novel organometallic complex having high heat resistance is provided. The organometallic complex, which includes a structure represented by General Formula (G1), includes iridium and a ligand. The ligand has a pyrazine skeleton. Iridium is bonded to nitrogen at the 1-position of the pyrazine skeleton. A phenyl group that has an alkyl group as a substituent is bonded at each of the 2- and 3-positions of the pyrazine skeleton, and a phenyl group that has a cyano group as a substituent is bonded at the 5-position of the pyrazine skeleton. The ortho position of the phenyl group bonded at the 2-position of the pyrazine skeleton is bonded to iridium. In the formula, each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Each of R 1 to R 6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group. At least one of R 7 to R 11 represents a cyano group.
1. An organometallic complex comprising a structure represented by General Formula (G1):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein each of R 1 to R 6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group, and
wherein at least one of R 7 to R 11 represents a cyano group.
2. An organometallic complex comprising a structure represented by General Formula (G2):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein R 6 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R il independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or 10 unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group, and
wherein at least one of R 7 to R 11 represents a cyano group.
3. An organometallic complex represented by General Formula (G3):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein each of R 1 to R 6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group,
wherein at least one of R 7 to R 11 represents a cyano group, and
wherein L represents a monoanionic ligand.
4. An organometallic complex represented by General Formula (G4):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein R 6 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group,
wherein at least one of R 7 to R 11 represents a cyano group, and
wherein L represents a monoanionic ligand.
5. The organometallic complex according to claim 3 or 4 ,
wherein the monoanionic ligand is a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, a monoanionic bidentate chelate ligand in which two coordinating elements are both nitrogen, or an aromatic heterocyclic bidentate ligand which can form a metal-carbon bond with iridium by cyclometalation.
6. The organometallic complex according to claim 3 or 4 ,
wherein the monoanionic ligand is represented by any one of General Formulae (L1) to (L6),
wherein each of R 71 to R 94 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms,
wherein each of A 1 to A 3 independently represents nitrogen, sp 2 hybridized carbon bonded to hydrogen, or sp 2 hybridized carbon having a substituent,
wherein the substituent is an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group,
wherein each of B 1 to B 8 independently represents nitrogen or substituted or unsubstituted carbon, and
wherein the substituent is an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group.
7. An organometallic complex represented by General Formula (G5):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein each of R 1 to R 6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group, and
wherein at least one of R 7 to R 11 represents a cyano group.
8. An organometallic complex represented by General Formula (G6):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein R 6 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group, and
wherein at least one of R 7 to R 11 represents a cyano group.
9. An organometallic complex represented by General Formula (G7):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein each of R 1 to R 6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group, and
wherein at least one of R 7 to R 11 represents a cyano group.
10. An organometallic complex represented by General Formula (G8):
wherein each of A 1 to A 4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
wherein R 6 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,
wherein each of R 7 to R 11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group, and
wherein at least one of R 7 to R 11 represents a cyano group.
11. The organometallic complex according to any one of claims 1 - 4 and 7 - 10 ,
wherein at least one of R 7 to R 11 represents an alkyl group having 1 to 6 carbon atoms.
12. The organometallic complex according to any one of claims 1 - 4 and 7 - 10 ,
wherein at least one of R 7 and R 11 represents an alkyl group having 1 to 6 carbon atoms.
13. An organometallic complex represented by Structural Formula (100)
14. A light-emitting element comprising the organometallic complex according to any one of claims 1 - 4 , 7 - 10 , and 13 .