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US 8,859,111 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsAmir Hossain Parham, Susanne Heun, Esther Breuning
Life of this patent
Estimating the term…
Abstract
The present invention relates to 4,4′-substituted spirobifluorenes which are suitable, owing to excellent properties, as functional materials in organic electroluminescent devices. In addition, the present invention relates to a process for the preparation of 4,4′-substituted spirobifluorenes and to the use of these compounds in organic electroluminescent devices.
Claims19
A compound of formula I
- wherein
- R is selected on each occurrence, identically or differently, from the group consisting of F, CN, NO2, ArNAr2, NAr2, C(═O)Ar, C(═O)R2, P(═O)Ar2, S(═O)Ar, S(═O)2Ar, —CR2═C(R2)2 and a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more non-aromatic radicals R1;
- two radicals Ar which are bonded to the same nitrogen or phosphorus atom are optionally linked to one another by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C═O, C═NR2, C═C(R2)2, O, S, S═O, SO2, N(R2), P(R2) and P(═O)R2;
- R1 is selected, identically or differently on each occurrence, from the group consisting of H, D, F, OH, CN, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms and a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, C═O, C═S, C═NR2, P(═O)(R2), SO, SO2, NR2, O or S and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2;
- where, in addition, the respective R1 which is located in the vicinal position to the radical R, in the case where R is an aromatic or heteroaromatic ring system, is optionally a divalent unit which is linked to the group R;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R1;
- R2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN and an aliphatic, aromatic or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F, CN, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms;
- two or more adjacent substituents R2 may also be linked to one another by a covalent bond or also, in the case where the R2 involved are aromatic or heteroaromatic hydrocarbon radicals, by one or more divalent aliphatic hydrocarbon units.
5 more elements
Dependencies are inferred from the claim text.