Metal complexes
The present invention describes novel ionic metal complexes. Compounds of this type can be employed as functional materials in a number of different applications which can be ascribed to the electronics industry in the broadest sense. The compounds according to the invention are described by the formulae (1) and (1a).
1. An ionic compound of formula (1)
[M(L) t+/t− n (L′) m (L″) o ][ion] t−/t+ n (1)
wherein sub-structure M(L) t+/t− n , as cation or anion, is of formula (2a)
wherein
M is iridium or platinum;
D is N;
X is, CR 1 ;
X 1 is CR 1 or N;
Q is, identically or differently on each occurrence, a; a charged substituent selected from positively charged substituents selected from heterocyclic compounds based on pyridine, imidazole, thiazole, isothiazole, oxazole, isoxazole, quinoline, isoquinoline, pyridazine, rimidine razine urine. henazine or mixtures thereof, or said charged heterocyclic group is optionally substituted with one or more radicals R 1 or
—N + (R) 3 , —P + (R) 3 , —As + (R) 3 , —Sb + (R) 3 , or
wherein
w is an integer 1, 2, 3, 4, or 5;
X is defined above; and
R is, identically or differently on each occurrence, H, deuterium, F, CN, a straight-chain alkyl or alkoxy group having up to 40 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms, where one or more non-adjacent CH 2 groups of said straight-chain alkyl or alkoxy group and said branched or cyclic alkyl or alkoxy group is optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , —O—, —S—, —NR 2 —, —(C═O)—, —(C═NR 2 )—, —P═O(R 2 )—, or —CONR 2 —, and wherein one or more H atoms is optionally replaced by F,
or
an aromatic or aryloxy system having 6 to 30 C atoms or a heteroaromatic or heteroaryloxy system having 2 to 30 C atoms, wherein said aromatic or aryloxy system and said heteroaromatic or heteroaryloxy system are optionally substituted by one or more radicals R 1 ; and wherein two or more radicals R on the same ring or on different rings optionally define a further aliphatic or aromatic ring system with one another,
or alternatively selected from negatively charged substituents selected from the group consisting of —R—O − , —R—COO − , —R—SO 3 − , —COO − , —O − , —S − , —SO 2 − , —SO 3 − , —SO 4 2− , —PO 2 2− , —PO 3 2− , —PO 4 2− ;
wherein
R is defined above,
R 1 is, identically or differently on each occurrence, H, deuterium, F, Cl, Br, I, OH, NO 2 , CN, N(R 2 ) 2 , B(OH) 2 , B(OR 2 ) 2 , a straight-chain alkyl or alkoxy group having up to 40 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms, wherein one or more non-adjacent CH 2 groups in said straight-chain alkyl or alkoxy groups and said branched or cyclic alkyl or alkoxy group are optionally replaced by —R 2 C═CR 2 —,—C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , —O—, —S—, —NR 2 —, —(C═O)—, —(C═NR 1 )—, —P═O(R 2 )—, —COOR 2 —, or —CONR 2 —, and wherein one or more H atoms are optionally replaced by F,
or
an aromatic or aryloxy system having 6 to 30 C atoms, a heteroaromatic or heteroaryloxy system having 2 to 30 C atoms, wherein said aromatic, aryloxy, heteroaromatic, and heteroaryloxy systems are optionally substituted by one or more non-aromatic radicals R 1 , wherein a plurality of R 1 , either on the same ring or on different rings, optionally define a further mono- or polycyclic, aliphatic or aromatic ring system;
R 2 is, identically or differently on each occurrence, H, an aliphatic hydrocarbon radical having up to 20 C atoms, an aromatic hydrocarbon radical having 6 to 20 C atoms, or a heteroaromatic hydrocarbon radical having 2 to 30 C atoms;
k is, identically or differently on each occurrence, 0, 1, 2, 3, or 4, wherein at least one k is not equal to 0;
n is 1, 2 or 3;
t is 1, 2, or 3, wherein the ligand itself carries the charge; and
wherein ligands L′ and L″ are monoanionic ligands which chelate in a bidentate manner;
m and o are, identically or differently on each occurrence, 0, 1, or 2; wherein at least one group Q is present on the structure of formula (2a); and an ion which acts as counterion to the complex ion [M(L) t+/t− n (L′) m (L″) o ].
2. The ionic compound of claim 1 , wherein said compound has the formula (1a)
[M(L) t+/t− n (L′) m (L″) o ][ion] t−/t+ n (1a)
wherein sub-structure M(L) t+/t− n is of formula (2b)
and optionally comprises sub-structure M(L′) m of formula (3)
wherein
X is, CR 1 ;
X 1 is CR 1 or N;
A is, identically or differently on each occurrence, —CR 1 —, —N═CR 1 —, —P═CR 1 —, —N═N—, —P═N—, NR 1 , O, or.
3. The ionic compound of claim 1 , wherein said ionic compound is in the form of a mixed salt.
4. The ionic compound of claim 3 , wherein said ionic compound of formula (1) comprises a sub-structure M(L) t+ n with a cationic ligand and the anion is formed from a sub-structure M(L) t− n with an anionic ligand as counterion.
5. The ionic compound of claim 1 , wherein Q is a charged heterocyclic group based on pyridine, imidazole, thiazole, isothiazole, oxazole, isoxazole, quinoline, isoquinoline, pyridazine, pyrimidine, pyrazine, purine, phenazine, or mixtures thereof, wherein said charged heterocyclic group is optionally substituted with one or more radicals R 1 .
6. The ionic compound of claim 1 , wherein Q is, identically or differently on each occurrence, —N + (R) 3 , —P + (R) 3 , —As + (R) 3 , —Sb + (R) 3 , —Bi + (R) 3 , —S + (R) 2 , —Se + (R) 2 , —Te + (R) 2 , or
wherein
w is an integer 1, 2, 3, 4, or 5;
X is, CR 1 , and
R is, identically or differently on each occurrence, H, deuterium, F, CN, a straight-chain alkyl or alkoxy group having up to 40 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms, where one or more non-adjacent CH 2 groups of said straight-chain alkyl or alkoxy group and said branched or cyclic alkyl or alkoxy group is optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , —O—, —S—, —NR 2 —, —(C═O)—, —(C═NR 2 )—, —P═O(R 2 )—, or —CONR 2 —, and wherein one or more H atoms is optionally replaced by F,
or
an aromatic or aryloxy system having 6 to 30 C atoms or a heteroaromatic or heteroaryloxy system having 2 to 30 C atoms, wherein said aromatic or aryloxy system and said heteroaromatic or heteroaryloxy system are optionally substituted by one or more radicals R 1 ; and wherein two or more radicals R on the same ring or on different rings optionally define a further aliphatic or aromatic ring system with one another.
7. The ionic compound of claim 1 , wherein Q is, identically or differently on each occurrence, —B − (R) 3 , —Al − (R) 3 , —Ga − (R) 3 , —In − (R) 3 , —Tl − (R) 3 , —Si 2− (R) 5 , —Ge 2− (R) 5 , —Sn 2− (R) 5 , —Pb 2− (R) 5 , —R—O − , —R—S − , —R—COO − , —R—CSS − , —R—SO 3 − , —COO − , —CSS − , —O − , —S − , —Se − , —Te − , —SO 2 − , —SO 3 − , —SO 4 2− , —PO 2 2− , —PO 3 2− , —PO 4 2− , [PHal 5 ] − , [AsHal 5 ] − , [SbHal 5 ] − , AuCl 3 − , PtCl 5 2− , Fe(CN) 5 2−/3− , polyelectrolytes, or ion exchanger resins;
wherein
Hal is chlorine, bromine, iodine, fluorine, or pseudohalides; and
R is, identically or differently on each occurrence, H, deuterium, F, CN, a straight-chain alkyl or alkoxy group having up to 40 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms, where one or more non-adjacent CH 2 groups of said straight-chain alkyl or alkoxy group and said branched or cyclic alkyl or alkoxy group is optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , —O—, —S—, —NR 2 —, —(C═O)—, —(C═NR 2 )—, —P═O(R 2 )—, or —CONR 2 —, and wherein one or more H atoms is optionally replaced by F,
or
an aromatic or aryloxy system having 6 to 30 C atoms or a heteroaromatic or heteroaryloxy system having 2 to 30 C atoms, wherein said aromatic or aryloxy system and said heteroaromatic or heteroaryloxy system are optionally substituted by one or more radicals R 1 ; and wherein two or more radicals R on the same ring or on different rings optionally define a further aliphatic or aromatic ring system with one another.
8. The ionic compound of claim 1 , wherein Q is bonded in the para-position to the bond to the metal M.
9. The ionic compound of claim 1 , wherein a plurality of radicals R 1 , either on the same ring or on different rings, define one or more aromatic or aliphatic ring systems.
10. The ionic compound of claim 1 , wherein R 1 is, identically or differently on each occurrence, H, F, CN, methyl, tert-butyl, phenyl, CF 3 , or a fused cyclic alkoxy group having 1 to 4 C atoms.
11. The ionic compound of claim 1 , wherein at least one of R 1 is an alkyl and/or alkoxy chain having at least four C atoms and/or Q is substituted with one or more long-chain radicals R 1 having at least four C atoms.
12. A conjugated, partially conjugated, or non-conjugated oligomer, polymer, or dendrimer comprising one or more of the ionic compounds of claim 1 .
13. A solution comprising the ionic compound of claim 1 or oligomers, polymers, or dendrimers thereof.
14. An organic electronic component comprising the ionic compound of claim 1 or oligomers, polymers, and/or dendrimers thereof.
15. The organic electronic device comprising the ionic compound of claim 1 , or oligomers, polymers, and/or dendrimers thereof, wherein said device is selected from the group consisting of organic light-emitting diodes, polymeric light-emitting diodes, organic organic integrated circuits, organic solar cells, organic fields-quench devices, and organic laser diodes.