Metal complexes
View Patent ↗The present invention relates to new types of metal complexes. Such compounds can be used as active components (=functional materials) in a series of different types of applications which can be classed within the electronics industry in the widest sense. The inventive compounds are described by the structure 1 and the formulae (1) to (60).
1. A compound of the structure 1,
containing at least one metal Met, wherein Met is a transition metal, Group III metal or f-block metal, coordinated to a polypodal ligand Lig of the structure 2,
where V is a bridging unit, characterized in that the three part-ligands L1, L2 and L3 which may be the same or different at each instance are covalently bonded to one another, and where V is CR, COH, COR 1 , CF, CCl, CBr, C—I, CN(R 1 ) 2 , RC(CR 2 ) 3 , RC(SiR 2 ) 3 ;
R is the same or different at each instance and is H, F, Cl, Br, I, NO 2 , CN, a straight-chain or branched or cyclic alkyl or alkoxy group having from 1 to 20 carbon atoms, in which one or more nonadjacent CH 2 groups may be replaced by —R 1 C═CR 1 —, —C≡C—, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , —O—, —S—, —NR 1 — or —CONR 1 —, and in which one or more hydrogen atoms may be replaced by F, or an aryl or heteroaryl group which has from 1 to 14 carbon atoms and may be substituted by one or more nonaromatic R radicals, where a plurality of substituents R, both on the same ring and on the two different rings, together may in turn form a further mono- or polycyclic, aliphatic or aromatic ring system;
R 1 is the same or different at each instance and is an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms;
and where the three part-ligands L1, L2 and L3 satisfy the structure 3
where Cy1 is a substituted or unsubstituted 2-pyridyl connected to V and Cy2 are the same or different at each instance and correspond to substituted or unsubstituted aromatic homocycles of carbon or substituted or unsubstituted aromatic heterocycles, which are each bonded ionically, covalently or coordinatively to the metal via a ring atom or via an atom bonded exocyclically to the homo- or heterocycle,
the zig-zag line is a direct bond linkage between Cy1 to Cy2,
and that the compounds of the structure 1 are uncharged.
2. The compound as claimed in claim 1 , wherein L1=L2=L3.
3. The compound as claimed in claim 1 , wherein the polypodal ligand Lig of the structure 4 generates facial coordination geometry on the metal Met
4. A metal complex which comprises the compound as claimed in claim 1 , selected from the compounds (1) 1 and (2) 1 ,
where the symbols and indices are each defined as follows:
M is Al, Ga, In, Tt, P, As, Sb, Bi, Sc, Y, La, V, Nb, Ta, Cr, Mo, W, Fe, Ru, Os, Co, Rh, Ir, Cu, Au, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb or Lu;
X is the same or different at each instance and is CR, N or P;
Y is the same or different at each instance and is NR 1 , O, S, Se, Te, SO, SeO, TeO, SO 2 , SeO 2 or TeO 2 ;
Z is the same as defined for V
R is the same or different at each instance and is H, F, Cl, Br, I, NO 2 , CN, a straight-chain or branched or cyclic alkyl or alkoxy group having from 1 to 20 carbon atoms, in which one or more nonadjacent CH 2 groups may be replaced by —R 1 C═CR 1 —, —C≡C—, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , —O—, —S—, —NR 1 — or —CONR 1 —, and in which one or more hydrogen atoms may be replaced by F, or an aryl or heteroaryl group which has from 1 to 14 carbon atoms and may be substituted by one or more nonaromatic R radicals, where a plurality of substituents R, both on the same ring and on the two different rings, together may in turn form a further mono- or polycyclic, aliphatic or aromatic ring system; and
R 1 is the same or different at each instance and is an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms and
c is the same or different at each instance and is 0 or 1.
5. The metal complex as claimed in claim 4 , wherein the symbol M=Al, Ga, In, Sc, Y, La, Ru, Os, Rh, Ir or Au.
6. The metal complex as claimed in claim 4 , wherein the symbol X═CR.
7. The metal complex as claimed in claim 4 , wherein the symbol Y═O or S.
8. The metal complex as claimed in claim 4 , wherein the symbol R═H, F, Cl, Br, I, CN, a straight-chain or branched or cyclic alkyl or alkoxy group having from 1 to 6 carbon atoms or an aryl or heteroaryl group which has from 3 to 8 carbon atoms and may be substituted by one or more nonaromatic R radicals, in which a plurality of substituents R, either on the same ring or on the two different rings, together may in turn form a further mono- or polycyclic, aliphatic or aromatic ring system.
9. The compound as claimed in claim 1 , wherein the compound has a purity (determined by means of 1 H NMR and/or HPLC) is more than 99%.
10. Conjugated, semiconjugated or nonconjugated polymers or dendrimers containing one or more compounds of the structure (1) as claimed in claim 1 .
11. Conjugated, semiconjugated or nonconjugated polymers or dendrimers as claimed in claim 10 , in which one or more of the R radicals is a bond to the polymer or dendrimer and
R is the same or different at each instance and is H, F, Cl, Br, I, NO 2 , CN, a straight-chain or branched or cyclic alkyl or alkoxy group having from 1 to 20 carbon atoms, in which one or more nonadjacent CH 2 groups may be replaced by —R 1 C═CR 1 —, —C≡C—, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , —O—, —S—, —NR 1 — or —CONR 1 —, and in which one or more hydrogen atoms may be replaced by F, or an aryl or heteroaryl group which has from 1 to 14 carbon atoms and may be substituted by one or more nonaromatic R radicals, where a plurality of substituents R, both on the same ring and on the two different rings, together may in turn form a further mono- or polycyclic, aliphatic or aromatic ring system; and
R 1 is the same or different at each instance and is an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms.
12. Polymers as claimed in claim 10 , characterized in that the polymer is selected from the group of polyfluorenes, poly-spiro-bifluorenes, poly-para-phenylenes, polycarbazoles, polyvinylcarbazoles, polythiophenes, or else from copolymers which have a plurality of the units specified here.
13. Polymers as claimed in claim 10 , characterized in that the polymer is soluble in organic solvents.
14. An electronic component comprising at least one compound as claimed in claim 1 .
15. The electronic component as claimed in claim 14 , characterized in that it is an organic light-emitting diode (OLED), organic integrated circuit (O-IC), organic field-effect transistor (OFET), organic thin-film transistor (OTFT), organic solar cell (O-SC) or organic laser diode (O-laser).
16. An electronic component comprising a polymer or dendrimer as claimed in claim 10 .