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US 11,456,421 B2Granted
Anthracene derivatives, luminescent materials and organic electroluminescent devices
AssigneeIdemitsu Kosan Co., Ltd.
InventorsMasahiro Kawamura, Mitsunori Ito
Life of this patent
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Abstract
Anthracene derivatives each having a structure including an anthracene skeleton, a phenanthrene skeleton selected from among various phenanthrene skeletons different in bonding site which is bonded to the 9-position of the anthracene skeleton and a group selected from among various aryl groups and so on which is bonded to the 10-position of the anthracene skeleton. Organic EL devices made by using the derivatives exhibit high light emission efficiency and a long life.
Claims33
An anthracene derivative, comprising a phenanthryl group, the anthracene derivative being represented by formula (1-1):
- wherein:
- L1 represents a single bond;
- Ar1 represents a group represented by formula (2):
- a substituted or unsubstituted fused aromatic ring group having 10 to 50 ring-forming carbon atoms, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that
- when Ar1 represents a group other than a group represented by formula (2), and a 1-position of the phenanthryl group is bonded to an anthracene skeleton, Ar1 is not an unsubstituted 1-phenanthryl group,
- when Ar1 represents a group other than a group represented by formula (2), and a 2-position of the phenanthryl group is bonded to the anthracene skeleton, Ar1 is not a substituted or unsubstituted 2-phenanthryl group, and
- when Ar1 represents a group other than a group represented by formula (2), and a 3-position of the phenanthryl group is bonded to the anthracene skeleton, Ar1 is not an unsubstituted 3-phenanthryl group;
- substituents Rx, Ra, and Rb each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted cycloakyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group having 6 to 50 ring-forming carbon atoms;
- “p” represents an integer of 1 to 8;
- “q” represents an integer of 0 to 9;
- and “y” represents an integer of 0 to 4;
- when “p” represents 2 to 8, “q” represents 2 to 9, or “v” represents 2 to 4, a plurality of Rx's, a plurality of Ra's, or a plurality of Rh's are identical to or different from each other, provided that a case where all Rx, Ra, and Rb each represent an anthracenyl group is excluded;
- and
- Arz represents a substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzofluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzochrysenyl group, and a substituted or unsubstituted heterocycle comprising group having 3 to 50 nucleus forming atoms,
- when Arz has a plurality of substituents, a plurality of adjacent substituents are optionally bonded to each other to form a saturated or unsaturated divalent group that completes a ring, when a phenanthrene skeleton is bonded at its 1- or 2-position to the anthracene skeleton, Arz represents a group except an unsubstituted phenyl group, and when the phenanthrene skeleton is bonded at its 3-position to the anthracene skeleton, Rx and Arz each represent a group except an unsubstituted carbazolyl group.
12 more elements
Dependencies are inferred from the claim text.