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US 7,125,998 B2Granted
Rhodium and iridium complexes
AssigneeMerck Patent GmbH
InventorsPhilipp Stossel, Hubert Spreitzer, Heinrich Becker
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel organometallic compounds which are phosphorescence emitters. Compounds of this type can be used as active components (=functional materials) in a series of different types of, application which can be classed within the electronics industry in the broadest sense. The compounds according to the invention are described by the formulae (I), (Ia), (II), (IIa), (V), (VII), (IX), (XI), (XIII) and (XV).
Claims83
A compound of the formula (I) or (II)
- wherein
- M is Rh or lr,
- X is the same or different and is F, Cl, Br or I,
- Y is the same or different and is 0, S or Se,
- R is the same or different at each occurrence and is H, F, Cl, Br, NO2, CN, a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH2 groups is optionally replaced by —O—, —S—, —NR1— or —CONR2— and in which one or more hydrogen atoms in said alkoxy group is optionally replaced by F, or an aryl or heteroaryl group having from 4 to 14 carbon atoms which is optionally substituted by one or more nonaromatic R radicals;
- and
- a plurality of R substituents, either on the same ring or on the two different rings together in the same ligand in turn optionally encompasses a further monocyclic carbon ring system;
- R1 and R2 are the same or different and are each H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms,
- a is the same or different and is 0, 1, 2, 3 or 4,
- b is the same or different and is 0, 1, 2 or 3, and
- n is 1, 2 or 3.
8 more elements
A compound of the formula (Ia) or (IIa)
- wherein
- M is Rh or Ir,
- X is the same or different and is F, Cl, Br or I,
- Y is the same or different and is 0, S or Se,
- R is the same or different at each occurrence and is H, F, Cl, Br, NO2, CN, a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH2 groups is optionally replaced by —O—, —S—, —NP1— or —CONR2— and in which one or more hydrogen atoms in said alkoxy group is optionally replaced by F, or an aryl or heteroaryl group having from 4 to 14 carbon atoms which is optionally substituted by one or more nonaromatic R radicals;
- and a plurality of R substituents, either on the same ring or on the two different rings together in the same ligand in turn optionally encompasses a further monocyclic carbon ring system;
- R1 and R2 are the same or different and are each H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms,
- a is the same or different and is 0, 1, 2, 3 or 4,
- b is the same or different and is 0, 1, 2 or 3, and
- n is 1, 2 or 3.
7 more elements
A compound of the formula (V) or (VII)
- wherein
- M is Rh or Ir,
- X is F, Cl, Br or I,
- Y is O, S or Se,
- Z is F, Cl, Br, I, O—R1, S—R1 or N(R1)2,
- R is the same or different at each occurrence and is H, F, Cl, Br, NO2, CN, a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH2 groups is optionally replaced by —O—, —S—, —NR1— or —CONR2— and in which one or more hydrogen atoms in said alkoxy group is optionally replaced by F, or an aryl or heteroaryl group having from 4 to 14 carbon atoms which is optionally substituted by one or more nonaromatic R radicals;
- and
- a plurality of R substituents, either on the same ring or on the two different rings in the same ligand together in turn optionally encompasses a further monocyclic carbon ring system;
- R1 and R2 are the same or different and are each H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms,
- a is 0, 1, 2, 3 or 4,
- b is 0, 1, 2 or 3, and
- p is 1 or 2.
9 more elements
A compound of the formula (IX), (XI), (XIII) or (XV)
- wherein
- M is Rh or Ir,
- X is F, Cl, Br or I,
- Y is O, S or Se,
- R is the same or different at each occurrence and is H, F, Cl, Br, NO2, CN, a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH2 groups is optionally replaced by —O—, —S—, —NR1— or —CONR2— and in which one or more hydrogen atoms in said alkoxy group is optionally replaced by F, or an aryl or heteroaryl group having from 4 to 14 carbon atoms which is optionally substituted by one or more nonaromatic R radicals;
- and
- a plurality of R substituents, either on the same ring or on the two different rings in the same ligand together in turn optionally encompasses a further monocyclic carbon ring system;
- R1 and R2 are the same or different and are each H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms,
- L1 is a neutral, monodentate ligand,
- L2 is a monoanionic, monodentate ligand,
- L3 is a neutral or mono- or dianionic bidentate ligand,
- a is 0, 1, 2, 3 or 4,
- b is 0, 1, 2, or 3,
- m is 0, 1 or 2, and
- p is 1 or 2.
12 more elements
A conjugated or semiconjugated polymer containing one or more compounds of the formula (I) and/or (II)
- and/or of the formula (Ia) and/or (IIa)
- and/or of the formula (IX), (XI), (XIII) and/or (XV)
- where the symbols and indices are defined as follows:
- M is Rh or lr,
- Y is the same or different and is O, S or Se,
- R is the same or different at each occurrence and is H, F, Cl, Br, NO2, CN, a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH2 groups is optionally replaced by —O—, —S—, —NR1— or —CONR2— and in which one or more hydrogen atoms in said alkoxy group is optionally replaced by F, or an aryl or heteroaryl group having from 4 to 14 carbon atoms which is optionally substituted by one or more nonaromatic R radicals;
- and
- a plurality of R substituents, either on the same ring or on the two different rings together in the same ligand in turn optionally encompasses a further monocyclic carbon ring system;
- R1 and R2 are the same or different and are H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms,
- L1 is a neutral, monodentate ligand,
- L2 is a monoanionic, monodentate ligand,
- L3 is a neutral or mono- or dianionic bidentate ligand,
- a is the same or different and is 0, 1, 2, 3 or 4,
- b is the same or different and is 0, 1, 2 or 3,
- n is 1, 2 or 3,
- m is 0, 1 or 2,
- p is 1 or 2, and
- X is a bond to the conjugated or semiconjugated polymer.
15 more elements
A compound of the formula (II)
- wherein
- M is Rh or lr,
- X, is the same or different and is F, Cl, Br or I,
- Y is the same or different and is 0, S or Se,
- R is the same or different at each occurrence and is H, F, Cl, Br, NO2, CN, a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH2 groups is optionally replaced by —O—, —S—, —NR1— or —CONR2— and in which one or more hydrogen atoms in said alkyl or alkoxy group is optionally replaced by F, or an aryl or heteroaryl group having from 4 to 14 carbon atoms which is optionally substituted by one or more nonaromatic R radicals;
- and
- a plurality of R substituents, either on the same ring or on the two different rings in the same ligand together in turn optionally encompasses a further monocyclic carbon ring system;
- R1 and R2 are the same or different and are each H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms,
- a is the same or different and is 0, 1, 2, 3 or 4, and
- n is 1, 2 or 3.
7 more elements
Dependencies are inferred from the claim text.