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US 11,530,224 B2Granted
Compounds with diazadibenzofurane or diazadibenzothiophene structures
AssigneeMerck Patent GmbH
InventorsAmir Parham, Thomas Eberle, Anja Jatsch, Tobias Grossmann, Jonas Kroeber
Life of this patent
Estimating the term…
Abstract
The present invention describes diazadibenzofuran or diazadibenzothiophene derivatives substituted by carbazole, fluorene, phenanthrene, benzofuran and/or benzothiophene groups, especially for use in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.
Claims52
A compound of formula (A):
- wherein
- Y1 is O or S;
- Y2 is C(R1)2, or —R1C═CR1—;
- W is the same or different in each instance and is N or CR1, with the proviso that not more than two W in one cycle are N, wherein the R1 radicals in the W groups do not form a fused heteroaromatic ring system;
- L1 is a bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more R1 radicals;
- A is the same or different in each instance and is N, CAra, or CArb, wherein exactly two A are N separated by at least one CAra or CArb group, with the proviso that A is CArb if two N are adjacent to this A;
- Ar is the same or different in each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more radicals R1;
- Ara is the same or different in each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more radicals R′;
- Arb is the same or different in each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more radicals R′;
- R1 is the same or different in each instance and is 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 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R2 radicals, wherein one or more nonadjacent CH2 groups are optionally replaced by —R2C═CR2—, Si(R2)2, C═O, C═S, C═NR2, —C(═O)O—, —C(═O)NR2—, NR2, P(═O)(R2), —O—, —S—, SO, or SO2, and wherein one or more hydrogen atoms are 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, each of which is optionally substituted by one or more R2 radicals, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms and which is optionally substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms and which is optionally substituted by one or more R2 radicals, or a combination of these systems;
- and wherein two or more R1 together optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- Ar1 is the same or different in each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more nonaromatic R2 radicals;
- and wherein two Ar1 bonded to the same silicon atom, nitrogen atom, phosphorus atom, or baron atom are optionally also joined together via 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;
- R2 is the same or different in each instance and is H, D, F, Cl, Br, I, CN, B(OR?3)2, CHO, C(═O)R3, CR3═C(R3)2, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, P(R3)2, B(R13)2, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R3 radicals, wherein one or more nonadjacent CH2 groups are optionally replaced by —R3C═CR3—, 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 wherein one or more hydrogen atoms are 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 and which is optionally substituted in each case by one or more R3 radicals, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms and which is optionally substituted by one or more R3 R3 radicals, or a combination of these systems;
- and wherein two or more adjacent R2 together optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- R3 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, wherein hydrogen atoms are also optionally replaced by F;
- and wherein two or more adjacent R3 together optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- n is 0, 1, 2, or 3.
15 more elements
A compound of formula (A):
- wherein
- Y1 is O or S;
- Y2 is N(Ar), O, C(R1)2, or —R1C═CR1—;
- W is the same or different in each instance and is N or CR1, with the proviso that not more than two W in one cycle are N, wherein the R1 radicals in the W groups do not form a fused heteroaromatic ring system;
- L1 is a bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more R1 radicals;
- A is the same or different in each instance and is N, CAra, or CArb, wherein exactly two A are N separated by at least one CAra or CArb group, with the proviso that A is CArb if two N are adjacent to this A;
- Ar is the same or different in each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more radicals R1;
- Ara is the same or different in each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more radicals R′;
- Arb is a group of formula (Arb-1):
- wherein
- L2 is a bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more R1 radicals;
- m is 0, 1, 2, 3, or 4;
- and
- the dotted line denotes the bond,
- R1 is the same or different in each instance and is 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 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R2 radicals, wherein one or more nonadjacent CH2 groups are optionally replaced by
- —R2C═CR2—, Si(R2)2, C═O, C═S, C═NR2, —C(═O)O—, —C(═O)NR2—, NR2, P(═O)(R2), —O—, —S—, SO, or SO2, and wherein one or more hydrogen atoms are 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, each of which is optionally substituted by one or more R2 radicals, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms and which is optionally substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms and which is optionally substituted by one or more R2 radicals, or a combination of these systems;
- and wherein two or more R1 together optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- Ar1 is the same or different in each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which is optionally substituted by one or more nonaromatic R2 radicals;
- and wherein two Ar1 bonded to the same silicon atom, nitrogen atom, phosphorus atom, or baron atom are optionally also joined together via 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;
- R2 is the same or different in each instance and is H, D, F, Cl, Br, I, CN, B(OR3)2, —CHO, C(═O)R3, CR3═C(R3)2, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, P(R3)2, B(R13)2, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R3 radicals, wherein one or more nonadjacent CH2 groups are optionally replaced by —R3C═CR3—, 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 wherein one or more hydrogen atoms are 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 and which is optionally substituted in each case by one or more R3 radicals, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms and which is optionally substituted by one or more R3 radicals, or a combination of these systems;
- and wherein two or more adjacent R2 together optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- R3 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, wherein hydrogen atoms are also optionally replaced by F;
- and wherein two or more adjacent R3 together optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- n is 0, 1, 2, or 3;
- with the proviso that,
- if Y2 is N(Ar) or O, Ara does not comprise any carbazole group, including any R1, R2, and R3 substituents bonded to Ara.
23 more elements
Dependencies are inferred from the claim text.