Biscarbazole derivative and organic electroluminescent element using same
A biscarbazole derivative having a specific group, which is represented by formula (1): and an organic electroluminescence device in which a plurality of organic thin-film layers including a light emitting layer are disposed between a cathode and an anode, and at least one of the organic thin-film layers include the biscarbazole derivative. The organic electroluminescence device exhibits high emission efficiency and has a long lifetime. In formula (1), each of A 1 and A 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; each of Y 1 to Y 16 independently represents C(R) or a nitrogen atom; each of R groups independently represents a hydrogen atom, etc.; and each of L 1 and L 2 independently represents a single bond, etc.; provided that at least one of A 1 , A 2 and R represents a substituted or unsubstituted fluoranthenyl group, etc.
1. A biscarbazole derivative represented by formula (2), (3), or (4):
wherein:
-L 1 -A 1 and -L 2 -A 2 are different from each other
A 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms;
A 1 represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted dibenzotriphenylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted benzo[b]fluoranthenyl group, a substituted or unsubstituted binaphthyl group, a substituted or unsubstituted dibenzophenanthrenyl group, a substituted or unsubstituted naphthotriphenylenyl group, or a substituted or unsubstituted benzofluorenyl group;
each of Y 1 to Y 16 independently represents C(R) and each of R groups independently represents a hydrogen atom, a substituent, or a valence bonded to a carbazole skeleton; and
each of L 1 and L 2 independently represents a single bond or a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
2. A material for an organic electroluminescence device, comprising:
the biscarbazole derivative according to claim 1 .
3. An organic electroluminescence device, comprising:
a plurality of organic thin-film layers between a cathode and an anode,
wherein the plurality of organic thin-film layers comprise a light emitting layer and at least one layer of the organic thin-film layers comprises the biscarbazole derivative according to claim 1 .
4. The organic electroluminescence device according to claim 3 ,
wherein the light emitting layer comprises the biscarbazole derivative as a host material.
5. The organic electroluminescence device according to claim 4 ,
wherein the light emitting layer comprises a phosphorescent material.
6. The organic electroluminescence device according to claim 5 ,
wherein the light emitting layer comprises the host material and the phosphorescent material which is an ortho-metallated complex of a metal atom selected from the group consisting of iridium (Ir), osmium (Os), and platinum (Pt).
7. The organic electroluminescence device according to claim 3 , further comprising:
a hole transporting layer between the anode and the light emitting layer,
wherein the hole transporting layer comprises the biscarbazole derivative.
8. A lighting device, comprising:
the organic electroluminescence device according to claim 3 .
9. A display device, comprising:
the organic electroluminescence device according to claim 3 .
10. The biscarbazole derivative according to claim 1 ,
wherein A 1 represents a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzophenanthrenyl group, or a substituted or unsubstituted benzotriphenylenyl group.
11. The biscarbazole derivative according to claim 10 ,
wherein A 1 represents an unsubstituted fluoranthenyl group, an unsubstituted benzophenanthrenyl group, or an unsubstituted benzotriphenylenyl group;
A 2 represents an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, or an unsubstituted naphthyl group;
at least one of L 1 and L 2 represents an unsubstituted, divalent phenyl group, an unsubstituted, divalent naphthyl group, or an unsubstituted, divalent phenanthrenyl group; and
each of Y 1 to Y 16 represents C(R) wherein each of R groups independently represents a hydrogen atom, or a valence bonded to a carbazole skeleton.
12. The biscarbazole derivative according to claim 10 ,
wherein A 1 represents an unsubstituted fluoranthenyl group, an unsubstituted benzophenanthrenyl group, or an unsubstituted benzotriphenylenyl group;
A 2 represents an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, or an unsubstituted naphthyl group;
L 1 and L 2 represent a single bond; and
each of Y 1 to Y 16 represents C(R) wherein each of R groups independently represents a hydrogen atom, or a valence bonded to a carbazole skeleton.
13. The biscarbazole derivative according to claim 1 ,
wherein A 2 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.
14. The biscarbazole derivative according to claim 1 ,
wherein at least one of L 1 and L 2 represents a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
15. The biscarbazole derivative according to claim 1 ,
wherein at least one of L 1 and L 2 represents a single bond.
16. The biscarbazole derivative according to claim 14 ,
wherein at least one of L 1 and L 2 represents a substituted or unsubstituted, divalent phenyl group, a substituted or unsubstituted, divalent naphthyl group, or a substituted or unsubstituted, divalent phenanthrenyl group.
17. The biscarbazole derivative according to claim 1 ,
wherein each of Y 1 to Y 16 represents C(R) wherein each of R groups independently represents a hydrogen atom, or a valence bonded to a carbazole skeleton.
18. The biscarbazole derivative according to claim 1 ,
wherein at least one of R groups represents a substituent and the substituent represents a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, and when a plurality of R groups represents the substituents, the plurality of R groups may be the same or different from each other.
19. The biscarbazole derivative according to claim 18 ,
wherein the substituent represents a methyl group, an ethyl group, a propyl group, or an isopropyl group, each being a substituted or unsubstituted.
20. The biscarbazole derivative according to claim 1 ,
wherein
when A 1 and A 2 have a substituent, the substituent represents a fluorine atom, a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted, linear, branched, or cyclic alkylsilyl group having 1 to 10 carbon atoms.
21. The biscarbazole derivative according to claim 20 ,
wherein the substituent represents a fluorine atom, an unsubstituted alkyl groups selected from methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, and n-octyl group, or an unsubstituted trimethylsilyl group.