[5]-helicene and dibenzofluorene materials for use in organic light emitting devices
AssigneeCanon Kabushiki Kaisha
InventorJian Ping Chen
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Abstract
Organic materials based on [5] helicenes or dibenzofluorenes are shown to have excellent properties for use in electroluminescent devices, including high stability and efficiency and low excimer formation. The materials may advantageously be adapted to have hole transport or electron transport capabilities in addition to emissive properties.
Claims24
An electroluminescent device, comprising:
- a transparent anode;
- a cathode;
- and
- a layer of emissive [5] helicene material between the anode and the cathode.
A method of making substituted [5] helicenes having hole transport ability in an EL device comprising the step of:
- aminating a dibromo [5] helicene in the presence of a phoshorous ligand and Pd(0) catalyst in basic conditions.
An electroluminescent device, comprising:
- a transparent anode;
- a cathode;
- and
- a layer of emissive dibenzofluorene material between the anode and the cathode.
A light emissive compound having hole transport capability, and having the following structure (I) or (II):
- 16
- wherein Ar and Ar′ are independently substituted or unsubstituted aromatic groups and said N atoms are bonded to two of carbon atoms 1-14 in structure (I) or carbon atoms 1-13 in structure (II), respectively, and
- wherein said carbons atoms 1-14 in structure (I) or 1-13 in structure (II) not bonded to said N atoms are unsubstituted or substituted with halogen atom, alkyl group, substituted alkyl group, alkoxy group, substituted alkoxy group, thioalkoxy group, substituted thioalkoxy group, cyano group, amino group, mono- or disubstituted amino group, hydroxyl group, mercapto group, aryloxy group, substituted aryloxy group, arylthio group, substituted arylthio group, carbocyclic aromatic group, substituted carbocyclic aromatic group, heterocyclic aromatic group, substituted heterocyclic aromatic group, heterocyclic group or a substituted heterocyclic group.
A light emissive compound having electron withdrawing groups bonded to a [5] helicene or dibenzofluorene core having the following structure (III) or (IV):
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- wherein X is oxygen, sulfur or substituted or unsubstituted nitrogen, and R is H or hydrocarbon
- wherein said electron withdrawing groups are bonded to two of carbon atoms 1-14 in structure (I) or carbon atoms 1-13 in structure (II), respectively, and wherein said carbon atoms 1-14 in structure (I) or 1-13 in structure (II) not bonded to said N atoms are unsubstituted or substituted with halogen atom, alkyl group, substituted alkyl group, alkoxy group, substituted alkoxy group, thioalkoxy group, substituted thioalkoxy group, cyano group, amino group, mono- or disubstituted amino group, hydroxyl group, mercapto group, aryloxy group, substituted aryloxy group, arylthio group, substituted arylthio group, carbocyclic aromatic group, substituted carbocyclic aromatic group, heterocyclic aromatic group, substituted heterocyclic aromatic group, heterocyclic group or a substituted heterocyclic group.
Dependencies are inferred from the claim text.