Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
A novel light-emitting material is provided. A novel orgnometallic complex is provided. An orgnometallic complex having a high carrier-transport property is provided. An orgnometallic complex having a deep HOMO level and/or a deep LUMO level is provided. An orgnometallic complex having a high charge-injection property is provided. Another object is to provide an organometallic complex that can exhibit yellow to blue phosphorescence. An organometallic complex that has a high carrier-transport property and exhibits green to blue phosphorescence is provided. An organometallic complex including a ligand having a structure of 5-(2-pyridinyl)-5H-benzimidazo[1,2-a]benzimidazole and a light-emitting material including the organometallic complex are provided.
1. A compound having a structure represented by a formula (G1)
M represents a Group 9 element or a Group 10 element, and
R 1 to R 11 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group.
2. The compound according to claim 1 , wherein:
the compound is represented by a formula (G2)
M represents a Group 9 element or a Group 10 element,
R 1 to R 11 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group,
L represents an aromatic heterocyclic bidentate ligand to form a metal-carbon bonding by cyclometalation or a monoanionic chelate ligand, and
when M is the Group 9 element, n represents 0, 1 or 2, m represents 1, 2 or 3, and n +m =3, and when M is the Group 10 element, n represents 0 or 1, m represents 1 or 2, and n +m =2.
3. The compound according to claim 2 , wherein L is bonded to one or more of R 1 to R 11 , directly or by cross-linking through any of carbon, silicon, oxygen, sulfur, and nitrogen.
4. The compound according to claim 2 , wherein:
M is platinum, and n represents 0 or 1, m represents 1 or 2, and n +m =2.
5. The compound according to claim 2 , wherein:
M is iridium, and
n represents 0, 1 or 2, m represents 1, 2 or 3, and n +m =3.
6. The compound according to claim 2 , wherein:
L is represented by one or more of formulae (L1) to (L12)
R 29 to R 32 and R 71 to R 102 each independently represent any one of 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, and a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms,
Ar represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
A 1 to A 3 each independently represent nitrogen, sp 2 hybridized carbon bonded to hydrogen, or sp 2 carbon bonded to a substituent R; A 4 to A 11 each independently represent nitrogen or sp 2 carbon bonded to a substituent R; and the substituent R is an alkyl group having 1to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group,
X 1 , Y 1 , Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each independently represent a nitrogen atom or a carbon atom,
when two or three of X 1 , Y 1 , and Z 1 each represent a carbon atom, the carbon atom has a substituent or no substituent,
in each of combinations of X 2 and Z 2 , Y 3 and Z 3 , and X 4 and Y 4 , when one represents a nitrogen atom, the other represents a carbon atom, and
when X 1 , Y 1 , Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each represent a carbon atom, the carbon atom has a substituent or no substituent.
7. A compound represented by a formula (G5)
wherein:
R 1 to R 11 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group,
A represents a five-membered heteroaromatic skeleton including two or three nitrogen atoms, and
Ar represents a divalent arylene group having 6 to 14 carbon atoms or a divalent heteroarylene group having 3 to 15 carbon atoms and 1 to 5 heteroatoms.
8. The compound according to claim 7 , wherein any one of carbon atoms bonded to R 1 to R 11 is bonded to any of elements in Ar, directly or by cross-linking through any of carbon, silicon, oxygen, sulfur, and nitrogen.
9. The compound according to claim 7 , wherein:
A represents any one of skeletons represented by formulae (p1) to (p4)
R 29 to R 31 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group,
X 1 , Y 1 , Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each independently represent a nitrogen atom or a carbon atom,
when two or three of X 1 , Y 1 , and Z 1 each represent a carbon atom, the carbon atom has a substituent or no substituent,
in each of combinations of X 2 and Z 2 , Y 3 and Z 3 , and X 4 and Y 4 , when one represents a nitrogen atom, the other represents a carbon atom, and
when X 1 , Y 1 , Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each represent a carbon atom, the carbon atom has a substituent or no substituent.
10. The compound according to claim 7 , wherein:
the compound is represented by a formula (G51)
and
R 25 to R 28 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group.
11. The compound according to claim 10 , wherein:
A represents any one of skeletons represented by formulae (p1) to (p4)
R 29 to R 31 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group,
X 1 , Y 1 , Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each independently represent a nitrogen atom or a carbon atom,
when two or three of X 1 , Y 1 , and Z 1 each represent a carbon atom, the carbon atom has a substituent or no substituent,
in each of combinations of X 2 and Z 2 , Y 3 and Z 3 , and X 4 and Y 4 , when one represents a nitrogen atom, the other represents a carbon atom, and
when X 1 , Y 1 , Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each represent a carbon atom, the carbon atom has a substituent or no substituent.
12. The compound according to claim 10 , wherein:
the compound is represented by a formula (G52)
and
R 33 to R 35 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group.
13. A compound represented by a formula (G53)
wherein:
R 1 to R 10 and R 25 to R 27 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group,
A represents a five-membered heteroaromatic skeleton including two or three nitrogen atoms,
Q represents any one of a single bond, a carbon atom, a silicon atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and
when Q represents a carbon atom or a silicon atom, Q has a substituent or no substituent.
14. The compound according to claim 13 , wherein:
A represents any one of skeletons represented by formulae (p1) to (p4)
R 29 to R 31 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group,
X 1 ,Y 1 ,Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each independently represent a nitrogen atom or a carbon atom,
when two or three of X 1 , Y 1 , and Z 1 each represent a carbon atom, the carbon atom has a substituent or no substituent,
in each of combinations of X 2 and Z 2 , Y 3 and Z 3 , and X 4 and Y 4 , when one represents a nitrogen atom, the other represents a carbon atom, and
when X 1 ,Y 1 , Z 1 , X 2 , Z 2 , Y 3 , Z 3 , X 4 , and Y 4 each represent a carbon atom, the carbon atom has a substituent or no substituent.
15. The compound according to claim 13 , wherein:
the compound is represented by a formula (G54)
and
R 33 to R 35 each independently represent any one of 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, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group.
16. The compound according to claim 13 , wherein the compound is represented by a formula (100)
17. The compound according to claim 7 , wherein R 1 to R 4 and R 6 to R 10 are each hydrogen, and R 5 is a methyl group.
18. The compound according to claim 13 , wherein R 1 to R 4 and R 6 to R 10 are each hydrogen, and R 5 is a methyl group.
19. The compound according to claim 10 , wherein R 25 to R 27 are each hydrogen.
20. The compound according to claim 13 , wherein R 25 to R 27 are each hydrogen.
21. The compound according to claim 12 , wherein R 33 to R 35 are each hydrogen.
22. The compound according to claim 15 , wherein R 33 to R 35 are each hydrogen.
23. The compound according to claim 7 , wherein the compound exhibits blue light.
24. The compound according to claim 13 , wherein the compound exhibits blue light.
25. A light-emitting material comprising the compound according to claim 7 .
26. A light-emitting material comprising the compound according to claim 13 .
27. A light-emitting element comprising the compound according to claim 1 .
28. A light-emitting element comprising the light-emitting material according to claim 25 .
29. A light-emitting element comprising the light-emitting material according to claim 26 .
30. A light-emitting device comprising the light-emitting element according to claim 27 .
31. A light-emitting device comprising the light-emitting element according to claim 28 .
32. A light-emitting device comprising the light-emitting element according to claim 29 .
33. An electronic device comprising the light-emitting device according to claim 30 .
34. An electronic device comprising the light-emitting device according to claim 31 .
35. An electronic device comprising the light-emitting device according to claim 32 .
36. A lighting device comprising the light-emitting device according to claim 30 .
37. A lighting device comprising the light-emitting device according to claim 31 .
38. A lighting device comprising the light-emitting device according to claim 32 .