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. A light-emitting element comprising:
a pair of electrodes,
a layer between the pair of electrodes,
wherein the layer comprises a π-electron deficient heteroaromatic compound, a π-electron rich heteroaromatic compound, and an organometallic complex 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. The light-emitting element according to claim 1 ,
wherein the π-electron deficient heteroaromatic compound is a nitrogen-containing heteroaromatic compound or a metal complex, and
wherein the π-electron rich heteroaromatic compound is an aromatic amine compound.
3. The light-emitting element according to claim 1 ,
wherein the organometallic complex comprising a structure represented by General Formula (G2):
4. A light-emitting device comprising:
the light-emitting element according to claim 1 ; and
a transistor or a substrate.
5. An electronic device comprising:
the light-emitting device according to claim 4 ; and
a microphone, a camera, an operation button, an external connection portion, or a speaker.
6. An electronic device comprising:
the light-emitting device according to claim 4 ; and
a housing or a touch sensor.
7. A light-emitting element comprising:
a pair of electrodes,
a layer between the pair of electrodes,
wherein the layer comprises a t-electron deficient heteroaromatic compound, a π-electron rich heteroaromatic compound, and 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.
8. The light-emitting element according to claim 7 ,
wherein the π-electron deficient heteroaromatic compound is a nitrogen-containing heteroaromatic compound or a metal complex, and
wherein the π-electron rich heteroaromatic compound is an aromatic amine compound.
9. The light-emitting element according to claim 7 ,
wherein the organometallic complex represented by General Formula (G4):
10. The light-emitting element according to claim 7 ,
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.
11. The light-emitting element according to claim 7 ,
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.
12. A light-emitting device comprising:
the light-emitting element according to claim 7 ; and
a transistor or a substrate.
13. An electronic device comprising:
the light-emitting device according to claim 12 ; and
a microphone, a camera, an operation button, an external connection portion, or a speaker.
14. An electronic device comprising:
the light-emitting device according to claim 12 ; and
a housing or a touch sensor.
15. A light-emitting element comprising:
a pair of electrodes,
a layer between the pair of electrodes,
wherein the layer comprises an organometallic complex represented by Structural Formula (108)
16. The light-emitting element according to claim 15 :
wherein the layer comprises a π-electron deficient heteroaromatic compound, a π-electron rich heteroaromatic compound.
17. The light-emitting element according to claim 15 ,
wherein the π-electron deficient heteroaromatic compound is a nitrogen-containing heteroaromatic compound or a metal complex, and
wherein the π-electron rich heteroaromatic compound is an aromatic amine compound.
18. A light-emitting device comprising:
the light-emitting element according to claim 15 ; and
a transistor or a substrate.
19. An electronic device comprising:
the light-emitting device according to claim 18 ; and
a microphone, a camera, an operation button, an external connection portion, or a speaker.