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US 11,649,249 B2Granted
Compounds for electronic devices
AssigneeMerck Patent GmbH
InventorsAmir Parham, Jonas Kroeber, Dominik Joosten, Aurélie Ludemann, Tobias Grossmann
Life of this patent
Estimating the term…
Abstract
The present application relates to bridged triarylamines conforming to a defined formula. These compounds are suitable for use in electronic devices. The present application further relates to processes for preparing the compounds, and to electronic devices comprising the compounds.
Claims18
A compound of formula (I)
- where the variables that occur are as follows:
- Y is the same or different at each instance and is selected from a single bond, O and S, where there is at least one Y group selected from O and S;
- Z1 is the same or different at each instance and is CR1, N or C, where a Z1 group is C in the specific case when a Y group is bonded to it;
- Ar1 is the same or different at each instance and is an aromatic ring system which has 6 to 24 aromatic ring atoms and may be substituted by one or more R2 radicals;
- Cbz is a divalent group of the formula (Cbz)
- substituted at each of its unoccupied positions by an R3 radical, where one of the two bonds of the divalent group to the rest of the compound is the dotted bond on the nitrogen atom of the formula (Cbz),
- where the second of these two bonds may be at any unoccupied position in the group, and where
- Z2 is the same or different at each instance and is selected from C and N;
- Ar2 is selected from the formulae
- where the variables that occur are defined as follows:
- V is the same or different at each instance and is N or CR4, where at least one V group in each of formulae (Ar2-A), (Ar2-D) and (Ar2-E) is N;
- W is the same or different at each instance and is N or CR4;
- U is NR4;
- where at least one group selected from W and V groups in formula (Ar2—B) is N;
- and
- where one R4 group per formula is replaced by the bond to the Ar1 group or Cbz;
- R1, R2, R4 are the same or different at each instance and are selected from H, D, F, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, 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 two or more R1 or R2 or R3 or R4 radicals may be joined to one another and may form a ring;
- 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 R5 radicals;
- and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R5C═CR5—, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5—, NR5, P(═O)(R5), —O—, —S—, SO, SO2;
- R3 are the same or different at each instance and are selected from H, D, F, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, 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, and aromatic ring systems having 6 to 40 aromatic ring atoms;
- where two or more or R3 or R4 radicals may be joined to one another and may form a ring;
- where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems;
- and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R5C═CR5—, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5—, NR, P(═O)(R5), —O—, —S—, SO, SO2;
- R5 is the same or different at each instance and is selected from H, D, F, C(═O)R6, CN, Si(R6)3, N(R6)2, P(═O)(R6)2, S(═OR6, S(═O)R6, S(═O)2R6, 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 two or more R5 radicals may be joined to one another and may form a ring;
- 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 R6 radicals;
- and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R6C═CR6—, —C≡C—, Si(R6)2, C═O, C═NR6, —C(═O)O—, —C(═O)NR6—, NR6, P(═O)(R6), —O—, —S—, SO, or SO2;
- R6 is the same or different at each instance and is selected from H, D, F, CN, alkyl or alkoxy groups having 1 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 two or more R6 radicals may be joined to one another and may form a ring;
- and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by F or CN;
- i is the same or different at each instance and is 0 or 1, where at least two indices i in formula (I) are 1, and where the Y group in question is absent when the corresponding index i=0;
- n is 0, 1, 2, 3 or 4;
- and
- m is 0, 1, 2, 3 or 4.
32 more elements
A compound of formula (I)
- where the variables that occur are as follows:
- Y is the same or different at each instance and is selected from a single bond, O and S, where there is at least one Y group selected from O and S;
- Z1 is the same or different at each instance and is CR1, N or C, where a Z1 group is C in the specific case when a Y group is bonded to it;
- Ar1 is the same or different at each instance and is an aromatic ring system which has 6 to 24 aromatic ring atoms and may be substituted by one or more R2 radicals;
- Cbz is a divalent group of the formula (Cbz)
- substituted at each of its unoccupied positions by an R3 radical, where one of the two bonds of the divalent group to the rest of the compound is the dotted bond on the nitrogen atom of the formula (Cbz),
- where the second of these two bonds may be at any unoccupied position in the group, and where Z2 is the same or different at each instance and is selected from C and N;
- Ar2 is selected from triazine and quinazoline that may each be substituted by one or more R4 radicals;
- R1, R2, R4 are the same or different at each instance and are selected from H, D, F, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, 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 two or more R1 or R2 or R3 or R4 radicals may be joined to one another and may form a ring;
- 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 R5 radicals;
- and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R5C═CR5—, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5—, NR5, P(═O)(R5), —O—, —S—, SO, SO2;
- R3 are the same or different at each instance and are selected from H, D, F, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, 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, and aromatic ring systems having 6 to 40 aromatic ring atoms;
- where two or more or R3 or R4 radicals may be joined to one another and may form a ring;
- where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems;
- and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R5C═CR5—, —C≡C—, Si(R5)2, C═O, C═NR5, —C(═O)O—, —C(═O)NR5—, NR5, P(═O)(R5), —O—, —S—, SO, SO2;
- R5 is the same or different at each instance and is selected from H, D, F, C(═O)R6, CN, Si(R6)3, N(R6)2, P(═O)(R6)2, OR6, S(═O)R6, S(═O)2R6, 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 two or more R5 radicals may be joined to one another and may form a ring;
- 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 R6 radicals;
- and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R6C═CR6—, —C≡C—, Si(R6)2, C═O, C═NR6, —C(═O)O—, —C(═O)NR6—, NR6, P(═O)(R6), —O—, —S—, SO, or SO2;
- R6 is the same or different at each instance and is selected from H, D, F, CN, alkyl or alkoxy groups having 1 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 two or more R6 radicals may be joined to one another and may form a ring;
- and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by F or CN;
- is the same or different at each instance and is 0 or 1, where at least two indices i in formula (I) are 1, and where the Y group in question is absent when the corresponding index i=0;
- n is 0, 1, 2, 3 or 4;
- and
- m is 0, 1, 2, 3 or 4.
24 more elements
Dependencies are inferred from the claim text.