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US 12,071,405 B2Granted
Materials for electronic devices
AssigneeMerck Patent GmbH
InventorsElvira Montenegro, Teresa Mujica-Fernaud, Florian Maier-Flaig, Frank Voges
Life of this patent
Estimating the term…
Abstract
The present application relates to compounds of formula (I) containing a group selected from amino groups, bridged amino groups and carbazole groups, to processes for preparation thereof, and to the use thereof in electronic devices, and in particular OLEDs.
Claims21
A compound of the formula (I-1)
- where the compounds may each be substituted by an R3 or R6 radical at the unoccupied positions on the aromatic rings, and where the variables that occur are as follows:
- Z1 is the same or different at each instance and is selected from CR1 and CR3;
- X1 is the same or different at each instance and is a divalent group selected from —C(R4)2—, —C(R4)2—C(R4)2—, —CR4—CR4— and —Si(R4)2—;
- R1 is the same or different at each instance and is a group of the formula (N)
- ArL is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R5 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R5 radicals;
- Ar2 is the same or different at each instance and is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R5 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R5 radicals;
- E is a single bond or a divalent group selected from the group consisting of C(R5)2, Si(R5)2, N(R5), O, and S;
- R2 is selected from H, and D;
- R3 is the same or different at each instance and is selected from H, D, F, CN, Si(R7)3, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems may each be substituted by one or more R7 radicals;
- R5 is the same or different at each instance and is selected from H, D, F, C(═O)R7, CN, Si(R7)3, N(R7)2, P(═O)(R7)2, OR7, S(═O)R7, S(═O)2R7, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
- where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned may each be substituted by one or more R7 radicals;
- and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R7C═CR7—, —C═C—, Si(R7)2, C═O, C═NR7, —C(═O)O—, —C(═O)NR7—, NR7, P(═O)(R7), —O—, —S—, SO or SO2;
- R4 is the same or different at each instance and is selected from H, D, F, CN, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
- where said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems may each be substituted by one or more R7 radicals;
- R6 is the same or different at each instance and is selected from H, D, F, CN, Si(R7)3, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
- where said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems may each be substituted by one or more R7 radicals;
- R7 is the same or different at each instance and is selected from H, D, F, CN, Si(R8)3, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems may each be substituted by one or more R8 radicals;
- R8 is the same or different at each instance and is selected from H, D, F, CN, alkyl groups having 1 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms;
- where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by F or CN;
- k is 0 or 1, where, in the case that k=0, the ArL group is absent and the nitrogen atom of the group of the formula (N) constitutes the attachment position;
- m is 0 or 1, where, in the case that m=0, the E group is absent and the Ar2 groups are not bonded to one another;
- i is 0, which means that the R1 group marked with index i is absent;
- and
- where there is at least one Z1 group that is CR1.
21 more elements
Dependencies are inferred from the claim text.