Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
View Patent ↗A novel organometallic complex which can emit phosphorescence is provided. A light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency is provided. The organometallic complex having an aryl triazine derivative as a ligand is represented by General Formula (G1) below as a representative of the organometallic complex of the present invention.
1. An organometallic complex having a structure represented by Formula (G1),
wherein:
R 1 represents any of an unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, and an unsubstituted naphthyl group;
R 2 represents hydrogen or an unsubstituted alkyl group having 1 to 4 carbon atoms;
Ar 1 represents a substituted or unsubstituted 1,2-phenylene group, an unsubstituted 1,2-naphthalene-diyl group, or an unsubstituted 2,3-naphthalene-diyl group; and
M represents iridium (Ir).
2. The organometallic complex according to claim 1 ,
wherein:
the organometallic complex is represented by Formula (G2);
R 3 to R 6 separately represent any of hydrogen, an unsubstituted alkyl group having 1 to 4 carbon atoms, an unsubstituted alkoxy group having 1 to 4 carbon atoms, an unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, an unsubstituted haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, and an unsubstituted naphthyl group.
3. An organometallic complex represented by Formula (G3),
wherein:
L represents a monoanionic ligand;
R 1 represents any of an unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, and an unsubstituted naphthyl group;
R 2 represents hydrogen or an unsubstituted alkyl group having 1 to 4 carbon atoms;
Ar 1 represents a substituted or unsubstituted 1,2-phenylene group, an unsubstituted 1,2-naphthalene-diyl group, or an unsubstituted 2,3-naphthalene-diyl group;
M represents iridium (Ir);
n represents 2, and
the monoanionic ligand is any of a monoanionic bidentate chelate ligand having a beta-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, and a monoanionic bidentate chelate ligand in which two ligand elements are both nitrogen.
4. The organometallic complex according to claim 3 ,
wherein:
the monoanionic ligand is represented by any of Formulae (L1) to (L6);
R 11 to R 42 separately represent any of hydrogen, an unsubstituted alkyl group having 1 to 4 carbon atoms, a halogen group, a vinyl group, an unsubstituted haloalkyl group having 1 to 4 carbon atoms, an unsubstituted alkoxy group having 1 to 4 carbon atoms, and an unsubstituted alkylthio group having 1 to 4 carbon atoms; and
A 1 to A 3 separately represent any of nitrogen, sp 2 hybridized carbon bonded to hydrogen, and sp 2 hybridized carbon bonded to any of an alkyl group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a phenyl group.
5. The organometallic complex according to claim 3 ,
wherein:
the organometallic complex is represented by Formula (G4);
R 3 to R 6 separately represent any of hydrogen, an unsubstituted alkyl group having 1 to 4 carbon atoms, an unsubstituted alkoxy group having 1 to 4 carbon atoms, an unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, an unsubstituted haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, and an unsubstituted naphthyl group.
6. The organometallic complex according to claim 5 ,
wherein:
the monoanionic ligand is represented by any of Formulae (L1) to (L6);
R 11 to R 42 separately represent any of hydrogen, an unsubstituted alkyl group having 1 to 4 carbon atoms, a halogen group, a vinyl group, an unsubstituted haloalkyl group having 1 to 4 carbon atoms, an unsubstituted alkoxy group having 1 to 4 carbon atoms, and an unsubstituted alkylthio group having 1 to 4 carbon atoms; and
A 1 to A 3 separately represent any of nitrogen, sp 2 hybridized carbon bonded to hydrogen, and sp 2 hybridized carbon bonded to any of an alkyl group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a phenyl group.
7. An organometallic complex represented by Formula (G5),
wherein:
R 1 represents any of an unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, and an unsubstituted naphthyl group;
R 2 represents hydrogen or an unsubstituted alkyl group having 1 to 4 carbon atoms;
Ar 1 represents an unsubstituted arylene group having 6 to 10 carbon atoms;
M represents iridium (Ir); and
n represents 3.
8. The organometallic complex according to claim 7 ,
wherein:
the organometallic complex is represented by Formula (G6);
R 3 to R 6 separately represent any of hydrogen, an unsubstituted alkyl group having 1 to 4 carbon atoms, an unsubstituted alkoxy group having 1 to 4 carbon atoms, an unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, an unsubstituted haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, and an unsubstituted naphthyl group.
9. The organometallic complex according to claim 3 , wherein the organometallic complex is represented by Formula (100),
10. The organometallic complex according to claim 3 , wherein the organometallic complex is represented by any of Formulae (112), (113), (132), and (133)
11. The organometallic complex according to claim 1 ,
wherein, in the case where the phenyl group and the 1,2-phenylene group have substituent, the phenyl group and the 1,2-phenylene group are separately substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
12. The organometallic complex according to claim 2 ,
wherein, in the case where the phenyl group has substituent, the phenyl group is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
13. The organometallic complex according to claim 3 ,
wherein, in the case where the phenyl group and the 1,2-phenylene group have substituent, the phenyl group and the 1,2-phenylene group are separately substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
14. The organometallic complex according to claim 3 ,
wherein Ar 1 represents any of the unsubstituted 1,2-phenylene group, the unsubstituted 1,2-naphthalene-diyl group, and the unsubstituted 2,3-naphthalene-diyl group.
15. The organometallic complex according to claim 3 ,
R 1 represents any of the unsubstituted alkyl group having 1 to 4 carbon atoms, the unsubstituted phenyl group, and the unsubstituted naphthyl group, and
wherein Ar 1 represents any one of the unsubstituted 1,2-phenylene group, the unsubstituted 1,2-naphthalene-diyl group, and the unsubstituted 2,3-naphthalene-diyl group.
16. The organometallic complex according to claim 5 ,
wherein, in the case where the phenyl group has substituent, the phenyl group is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
17. The organometallic complex according to claim 5 ,
wherein R 3 to R 6 separately represent any of hydrogen, an unsubstituted alkyl group having 1 to 4 carbon atoms, an unsubstituted alkoxy group having 1 to 4 carbon atoms, an unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, an unsubstituted haloalkyl group having 1 to 4 carbon atoms, an unsubstituted phenyl group, and an unsubstituted naphthyl group.
18. The organometallic complex according to claim 7 ,
wherein, in the case where the phenyl group and the 1,2-phenylene group have substituent, the phenyl group and the 1,2-phenylene group are separately substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
19. The organometallic complex according to claim 8 ,
wherein, in the case where the phenyl group has substituent, the phenyl group is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.