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US 12,108,665 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck KGaA
InventorsAmir Parham, Philipp Stoessel, Christian Ehrenreich
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.
Claims14
An electronic device comprising at least one compound of formula (1)
- wherein
- Z is the same or different at each instance and is O or S;
- A is R or Z;
- Rb is Ar or a free electron pair;
- where, when A=Z, the oxygen or sulfur atom represented by Z is bonded to the carbon atom via a double bond, and Rb is Ar;
- in addition, Rb is a free electron pair when A=R, and there is a double bond between the carbon atom to which A is bonded and the nitrogen atom to which Rb is bonded;
- Ra is the same or different and is R, or the two Ra groups together with the nitrogen atom and the carbon atom to which they bind form a group of one of the formulae (2), (3) and (4);
- R radical is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and which may be substituted by one or more R1 radicals;
- where the dotted bond in each case indicates the linkage within formula (1);
- X is the same or different at each instance and is CR or N;
- or two adjacent X groups are a group of the formula (5) or (6)
- where the dotted bonds indicate the linkage of this group in the formula (2), formula (3) or formula (4);
- Y is the same or different at each instance and is CR or N;
- W is the same or different at each instance and is NAr, O, S or C(R)2;
- Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals;
- R is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar′)2, N(R1)2, OAr′, Sar′, CN, NO2, OR1, SR1, COOR1, C(═O)N(R1)2, Si(R1)3, B(OR1)2, C(═O)R1,P═(O)(R1)2, S(═O)R1, S(═O)2R1, OSO2R1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2, groups may be replaced by Si(R1)2, C═O, NR1, O, S or CONR1, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and may be substituted in each case by one or more R1 radicals;
- at the same time, two R radicals together may also form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
- Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R1 radicals;
- R1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN NO2, OR2, SR2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by Si(R2)2, C═O, NR2, O, S or CONR2 and where one or more hydrogen atoms in the alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R2 radicals;
- at the same time, two or more R1 radicals together may form an aliphatic ring system;
- R2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F.
18 more elements
Dependencies are inferred from the claim text.