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US 2023/0147279 A1Published application
Heterocyclic compounds for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorPhilipp STOESSEL
Life of this patent
Estimating the term…
Abstract
The invention relates to heterocyclic compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.
Claims20
-19. (canceled)
A compound including at least one structure of formula (I)
- where the rings Ara and Arb are the same or different at each instance and are an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R radicals, where the rings Ara and Arb together may form a ring system;
- and where the further symbols and indices used are as follows:
- Z1, Z2, Z3 is the same or different at each instance and is N or B;
- W1, W2 is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) groups or the carbon atom and the nitrogen atom of the C═N group are each parts of the ring Ara or Arb, where the carbon atom of the C═N group binds to the V1 or V4 group;
- V1, V2 is the same or different at each instance and is —N═, —B═, ═C(Ar)— or ═C(R)—, or the V1, V2 groups form a ring of the formula
- where the ring Arc is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R radicals, where the ring Arc may form a ring system together with an X1 group or the rings Ara and Arc together may form a ring system, where W3 binds to the W1 group and is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) group or the carbon atom and the nitrogen atom of the C═N group are each parts of the Arc ring, where the carbon atom of the C═N group binds to the W1 group and the dotted lines represent the bonds to the W1 or Z2 group;
- V3, V4 is the same or different at each instance and is —N═, —B═, (Ar)C═C(Ar) or (R)C═C(R), or the V3, V4 groups form a ring of the formula
- where the ring Ard is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R radicals, where the ring Ard may form a ring system together with an X1 group or the rings Arb and Ard together may form a ring system, where W4 binds to the W2 group and is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) group or the carbon atom and the nitrogen atom of the C═N group are each parts of the Ara or Arb ring, where the carbon atom of the C═N group binds to the W2 group and the dotted lines represent the bonds to the W2 or Z3 group;
- Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals;
- the Ar group here may form a ring system with at least one Ar, X1, R group or a further group;
- X1 is the same or different at each instance and is N, CR1 or C if a ring system is formed by a bond to one of the rings Arc, Ard or a further group, with the proviso that not more than two of the X1, X2 groups in one cycle are N;
- X2 is the same or different at each instance and is N or CRb, with the proviso that not more than two of the X1, X2 groups in one cycle are N;
- R, Ra, Rb is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar′)2, N(R1)2, C(═O)OAr′, C(═O)OR1, C(═O)N(Ar′)2, C(═O)N(R1)2, C(Ar′)3, C(R1)3, Si(Ar′)3, Si(R1)3, B(Ar′)2, B(R1)2, C(═O)Ar′, C(═O)R1, P(═O)(Ar′)2, P(═O)(R1)2, P(Ar′)2, P(R1)2, S(═O)Ar′, S(═O)R1, S(═O)2Ar′, S(═O)2R1, OSO2Ar′, OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, 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 R1C═CR1, C≡C, Si(R1)2, C═O, C═S, C═Se, C═NR1, —C(═O)O—, —C(═O)NR1—, NR1, p(═O)(R1), —O—, —S—, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals;
- at the same time, two R, Ra, Rb radicals may also form a ring system together or with a further group;
- Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals;
- at the same time, it is possible for two Ar′ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R1), C(R1)2, Si(R1)2, C═O, C═NR1, C═C(R1)2, O, S, S═O, SO2, N(R1), P(R1) and P(═O)R1;
- R1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, N(Ar″)2, N(R2)2, C(═O)OAr″, C(═O)OR2, C(═O)Ar″, C(═O)R2, P(═O)(Ar″)2, P(Ar″)2, B(Ar″)2, B(R2)2, C(Ar″)3, C(R2)3, Si(Ar″)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 or an alkenyl groups having 2 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by —R2C═CR2—, —C≡C, Si(R2)2, C═O, C═S, C═Se, C═NR2, —C(═O)O—, —C(═O)NR2—, NR2, P(═O)(R2), —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems;
- at the same time, two or more R1 radicals together may form a ring system;
- at the same time, one or more R1 radicals may form a ring system with a further part of the compound;
- Ar″ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R2 radicals;
- at the same time, it is possible for two Ar″ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge 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 the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms;
- at the same time, two or more substituents R2 together may form a ring system;
- where at least one V1, V2, W1, W3 group represents N or B and at least one V3, V4, W2, W4 group represents N or B.
21 more elements
The compound as claimed in claim 24, wherein Z1 is N and at least one of the Z2, Z3, Z4, Z5 groups is B.
Dependencies are inferred from the claim text.