Polymeric, phosphorescent, organically semi-conductive emitter materials based on perarylated boranes, method for their production and use thereof
AssigneeOSRAM Opto Semiconductors GmbH
InventorsAndreas Kanitz, Wolfgang Rogler, Wolfgang Roth, Thomas Sonnabend, Jasmin Woerle
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Abstract
The invention relates to luminescent compounds with semi-conducting properties, as well as their production and their use in organic light-emitting diodes (OLEDs). The compounds are copolymers comprising a metal complex with a central atom from subgroup 8 of the periodic table of elements.
Claims13
A phosphorescent copolyaryl borane of type K,
- wherein:
- x, y and z are molar parts and add up to 1 and the molar parts y and z each are >0,
- hydrogen atoms are bonded at the ends,
- M, HT and TE each represent a type of arylene component,
- M is a matrix structure comprising an arylene structure, the arylene structure being any bivalently linking single- or multi-nucleic aromatic and/or heteroaromatic structure,
- HT is a substituted 2-amino-thiophene or 2-amino-thiazole structure with hole-transport capability,
- TE is a bivalent, phosphorescent organo-metallic complex of the following structure:
- wherein Me denotes a metal of group 8, 9 or 10, Ar5 is an arylene ligand that can form a complex with the metal Me and simultaneously is capable of polymeric linking,
- TE does not have the ligand (L-X) if the metal Me is platinum, and for all other Me L-X is a complex-forming ligand, and
- Ar is a carbocyclic or heterocyclic aryl moiety of which 0, 1 or more of the hydrogen atoms are each substituted by branched or linear aryl moieties or alkoxy moieties (C1 to C10), phenyl moieties or diphenyl or naphthylphenyl-amino groups.
A method for producing a phosphorescent copolyaryl borane of type K
- wherein x, y and z are molar parts and add up to 1 and the molar parts y and z each are >0,
- hydrogen atoms are bonded at the ends,
- M, HT and TE each represent a type of arylene component,
- M is a matrix structure comprising an arylene structure, the arylene structure being any bivalently linking single- or multi-nucleic aromatic and/or heteroaromatic structure,
- HT is a substituted 2-amino-thiophene or 2-amino-thiazole structure with hole-transport capability,
- TE is a bivalent, phosphorescent organo-metallic complex of the following structure:
- wherein Me denotes a metal of group 8, 9 or 10, Ar5 is an arylene ligand that can form a complex with the metal Me and simultaneously is capable of polymeric linking,
- TE does not have the ligand (L-X) if the metal Me is platinum, and for all other Me L-X is a complex-forming ligand, and
- Ar is a carbocyclic or heterocyclic aryl moiety of which 0, 1 or more of the hydrogen atoms are each substituted by branched or linear aryl moieties or alkoxy moieties (C1to C10), phenyl moieties or diphenyl or naphthylphenyl-amino groups
- in accordance with the general synthesis scheme:
- wherein the starting point is the bromo-substituted arylene component M, the hole transport component HT and the bromo-substituted phosphorescent organo-metallic complex TE, the method comprising:
- reversing the polarity of the component M, the component HT and the complex TE, either by way of a Grignard reaction or by lithiation to produce a magnesium halide compound or a lithiated compound;
- after the reversing, substituting the magnesium or lithium of the magnesium halide compound or the lithiated compound with boron using a boron trihalide to form products H;
- and
- in the products H of the substituting, substituting the halogens X on the boron with organic moieties Ar via a Grignard reagent or via a corresponding lithiated reagent.
A mixture of at least two different phosphorescing polyaryl boranes of type K, wherein in each individual component polymer two of the aspect ratio variables x, y or z have the value zero, wherein K has the following structure:
- wherein:
- hydrogen atoms are bonded at the ends,
- M, HT and TE each represent a type of arylene component,
- M is a matrix structure comprising an arylene structure, the arylene structure being any bivalently linking single- or multi-nucleic aromatic and/or heteroaromatic structure,
- HT is a substituted 2-amino-thiophene or 2-amino-thiazole structure with hole-transport capability,
- TE is a bivalent, phosphorescent organo-metallic complex of the following structure:
- wherein Me denotes a metal of group 8, 9 or 10, Ar5 is an arylene ligand that can form a complex with the metal Me and simultaneously is capable of polymeric linking,
- TE does not have the ligand (L-X) if the metal Me is platinum, and for all other Me L-X is a complex-forming ligand, and
- Ar is a carbocyclic or heterocyclic aryl moiety of which 0, 1 or more of the hydrogen atoms are each substituted by branched or linear aryl moieties or alkoxy moieties (C1 to C10), phenyl moieties or diphenyl or naphthylphenyl-amino groups
- wherein the mixture is one of:
- a homopolymer containing M and a homopolymer containing HT;
- a homopolymer containg HT and a homopolymer containing TE;
- a homopolymer containing M and a homopolymer containing TE;
- or
- a homopolymer containing M, a homopolymer containing HT and a homopolymer containing TE.
Dependencies are inferred from the claim text.