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US 8,361,638 B2Granted
Fluorine derivatives for organic electroluminescence devices
AssigneeMerck Patent GmbH
InventorsPhilipp Stoessel, Holger Heil, Dominik Joosten, Christof Pflumm, Anja Gerhard
Life of this patent
Estimating the term…
Abstract
The present invention relates to fluorine derivatives and organic electronic devices in which said compounds are used as a matrix material in the emitting layer and/or as a hole transport material, and/or as an electron blocking or exciton blocking material, and/or as an electron transport material.
Claims17
A compound of formula (1)
- wherein
- X is on each occurrence, identically or differently, CR1 or N, wherein a maximum of 3 X groups in each ring are N or wherein two directly adjacent X groups are a unit of formula (7)
- wherein the dashed bonds indicate the link of the unit of formula (7) to adjacent C or N atoms;
- Y is on each occurrence, identically or differently, a single bond or BR1, C(R1)2, C(═O), C(═NR1), C(═C(R1)2), Si(R1)2, P(═O)R1, O, S, S(═O), S(═O)2, C(R1)2—C(R1)2, C(R1)2—NR1, or CR1═CR1;
- is on each occurrence, identically or differently, CR1 or N, wherein a maximum of two Z in each ring are N;
- R is on each occurrence, identically or differently, NAr2, C(═O)Ar, P(═O)Ar2, or an aromatic or heteroaromatic ring system having from 5 to 30 aromatic ring atoms and is optionally substituted by one or more non-aromatic radicals R1;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having from 5 to 30 aromatic ring atoms and is optionally substituted by one or more non-aromatic radicals R1;
- wherein two Ar bonded to the same nitrogen or phosphorus atom are optionally linked to one another by a single bond or a bridge selected from the group consisting of 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 on each occurrence, identically or differently, H, F, Cl, Br, I, CHO, N(R2)2, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, CR2═CR2Ar, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group having from 1 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group having from 3 to 40 C atoms, wherein said straight-chain, branched, or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group is optionally substituted by one or more radicals R2, wherein one or more non-adjacent CH2 groups in said straight-chain, branched, or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S, or CONR2, and wherein one or more H atoms in said straight-chain, branched, or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thio-alkoxy group is optionally replaced by F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms and is optionally substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group haying from 5 to 60 aromatic ring atoms and is optionally substituted by one or more radicals R2, or a combination of these systems;
- and wherein two or more adjacent substituents R1 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R2 is on each occurrence, identically or differently, H, D, or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having from 1 to 20 C atoms, wherein H atoms of said aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical is optionally replaced by F;
- and wherein two or more adjacent substituents R2 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system with one another;
- n is 1 or 2;
- and
- with the proviso that said compound of formula (1) does not include the following compound:
12 more elements
Dependencies are inferred from the claim text.