Compounds with arylamine structures
AssigneeMerck Patent GmbH
InventorsAmir PARHAM, Dominik JOOSTEN, Aurélie LUDEMANN, Tobias GROSSMANN, Jonas KROEBER
Life of this patent
Estimating the term…
Abstract
The present invention describes arylamine derivatives which are substituted by diazanaphthalene groups, in particular for use in electronic devices. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to electronic devices containing same.
Claims21
-19. (canceled)
A compound containing at least one structure of the formula (I),
- where the following applies to the symbols used:
- is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R1;
- Z1, Z2, Z3, Z4 are X or C;
- Y1 is BR1, Si(R1)2, NR1, O, S, S═O or S(═O)2;
- Y2, Y3 are on each occurrence, identically or differently, BR1, Si(R1)2, C(R1)2, NR1, O, S, S═O or S(═O)2;
- X is on each occurrence, identically or differently, N or CR1, preferably CR1, or C if a radical Ara is bonded to X;
- X1 is on each occurrence, identically or differently, N or CR1;
- m, n, o, p are 0 or 1;
- Ara is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R1, where the radical Ara does not contain a carbazole group or form a carbazole group with the aryl or heteroaryl group to which Ara is bonded, including substituents R1, R2 and R3 which is optionally bonded to the radical Ara;
- Arb is an aromatic or heteroaromatic ring system having 5 to 45 aromatic ring atoms, which is optionally substituted by one or more radicals R1;
- R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R2)2, C(═O)Ar1, C(═O)R2, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R2)3, 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 or an alkenyl group having 2 to 40 C atoms, which may in each case be 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, —C(═O)O—, —C(═O)NR2—, NR2, P(50 O)(R2), —O—, —S—, SO or SO2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of these systems;
- two or more substituents R1 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R2;
- two radicals Ar1 which are bonded to the same Si atom, N atom, P atom or B atom may also be bridged 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;
- R2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, B(OR3)2, NO2, C(═O)R3, CR3═C(R3)2, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, P(R3)2, B(R3)2, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, a straight-chain alkyl, alkoxy or thio-alkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, C═O, C═S, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO or SO2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R3, or a combination of these systems;
- two or more substituents R2 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R3 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN and which is optionally substituted by one or more alkyl groups, each having 1 to 4 carbon atoms;
- two or more substituents R3 may form a mono- or polycyclic, aliphatic ring system with one another;
- with the proviso that at least two groups X1 in formula (I) stand for N, where, in the case where p=1, Z1, Z2 represent C and, in the case where n=1, Z3 represents C, and, in the case where o=1, Z4 represents C, and
- with the proviso that compounds of the formula (A)
- are excluded, where the symbols X, Arb and R1 used have the meaning given above and k is 0 or 1.
A process for the preparation of the compound according to Claim which comprises coupling a diarylaniine compound to a compound containing at least one diazanaphthyl group in a coupling reaction.
Dependencies are inferred from the claim text.