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US 11,365,167 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsRouven Linge, Lara-Isabel Rodriguez, Sebastian Meyer, Holger Heil, Miriam Engel, Aaron Lackner
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.
Claims20
A compound of formula (1):
- wherein
- Ar1 is on each occurrence, identically or differently, an aryl or heteroaryl group having 6 to 18 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R1, wherein at least one Ar1 has 10 or more aromatic ring atoms;
- Ar2 is on each occurrence, identically or differently, an aryl or heteroaryl group having 6 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R1;
- Ar3 and Ar4
- are on each occurrence, identically or differently, an aromatic or heteroaromatic ring systems having 5 to 25 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R1;
- wherein at least one Ar3 is a group of formula (Ar3-2) and/or at least one Ar4 is a group of formula (Ar4-2):
- wherein
- the dashed bonds in the group of formula (Ar3-2) indicate the bonding to Ar1 and to a group Ar3 or Ar4;
- the dashed bond in the group of formula (Ar4-2) indicates the bonding to Ar3;
- E1 stands for —C(R0)2;
- and
- the groups of formulae (Ar3-2) and (Ar4-2) are optionally substituted at each free position by a group R1;
- E is identically or differently on each occurrence, selected from the group consisting of —BR0—, —C(R0)2—, —C(R0)2—C(R0)2—, —C(R0)2—O—, C(R0)2—S—, —R0C═CR0—, —R0C═N—, —Si(R0)2—, —Si(R0)2—Si(R0)2—, —C(═O)—, —C(═NR0)—, —C(═C(R0)2—, —O—, —S—, —S(═O)—, —SO2—, —N(R0)—, —P(R0)—, and —P((═O)R0)—, wherein two groups E are optionally in a cis or trans position relative to each other;
- R0 and R1
- are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar5)2, C(═O)Ar5, P(═O)(Ar5)2, S(═O)Ar5, S(═O)2Ar5, NO2, Si(R2)3, B(OR2)2, OSO2R2, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, wherein in each case one or more non-adjacent CH2 groups are optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, P(═O)(R2), SO, SO2, O, S, or CONR2 and wherein one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R2, or an aryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, and wherein two adjacent substituents R0 and/or two adjacent substituents R1 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R2;
- R2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar5)2, C(═O)Ar5, P(═O)(Ar5)2, S(═O)Ar5, S(═O)2Ar5, NO2, Si(R3)3, B(OR3)2, OSO2R3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R3, wherein in each case one or more non adjacent CH2 groups is optionally replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, P(═O)(R3), SO, SO2, O, S, or CONR3 and wherein one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R3, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, and where two adjacent substituents R2 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R3;
- R3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, wherein in each case one or more non adjacent CH2 groups is optionally replaced by SO, SO2, O, or S and wherein one or more H atoms is optionally replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms;
- Ar5 is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R3;
- n is an integer from 2 to 20.
16 more elements
Dependencies are inferred from the claim text.