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US 2019/0058133 A1Published application
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsAmir Hossain PARHAM, Tobias GROSSMANN, Jonas Valentin KROEBER
Life of this patent
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Abstract
The present invention relates to compounds comprising a heterocyclic group substituted with a fluoranthene group and a particular aromatic or heteroaromatic group. The compounds are suitable for use in electronic devices, in particular organic electroluminescent devices, comprising these compounds. In some embodiments, the compounds are used as matrix materials for phosphorescent or fluorescent emitters as well as a hole-blocking or an electron-transport layer.
Claims16
-14. (canceled)
A compound of the formula (1) or (2),
- where the following applies to the symbols and indices used:
- X is O or S;
- ArS is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case also be substituted by one or more radicals R3;
- Ar is a condensed aryl group having 10 to 40 aromatic ring atoms,
- which may in each case be substituted by one or more radicals R3
- or Ar is a group of formula (Ar-1),
- with the proviso that Ar is not a fluoranthene;
- and where the dashed line represents the bond to ArS or, if ArS is absent, to the phenyl group of the heterocycle comprising X as depicted in formula (1) or (2);
- E is O, S, C(R0)2;
- wherein when t is 0 then the divalent bridge E is absent;
- R0, R1, R2, R3 are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)Ar1, P(═O)(Ar1)2, S(═O)Ar1, S(═O)2Ar1, (R4)C═C(R4)Ar1, CN, NO2, N(R4)2, Si(R4)3, B(OR4)2, B(R4)2, B(N(R4)2)2, OSO2R4, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R4, where one or more, CH2 groups is optionally replaced by (R4)C═C(R4), C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, P(═O)(R4), SO, SO2, N(R4), O, S or CON(R4) 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 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R4, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R4;
- two adjacent substituents R0, two or more adjacent substituents R1, two or more adjacent substituents R2 and/or two or more adjacent substituents R3 may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system with one another;
- Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R4;
- R4 is on each occurrence, identically or differently selected from the group consisting of H, D, F, Cl, Br, I, CN, Si(R5)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl with 3-40 C-atoms which is optionally substituted by one or more radicals R5, wherein each one or more non-adjacent CH2 groups by is optionally replaced C(R5)═C(R5), Si(R5)2, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5 and where one or more H atoms is optionally replaced by D, F, Cl, Br or I, an aromatic or heteroaromatic ring system having 6 to 40 carbon atoms which is optionally substituted by one or more radicals R5, an aryloxy group having 5 to 40 aromatic ring atoms which is optionally substituted by one or more radicals R5, or an aralkyl group having 5 to 40 aromatic ring atoms which is optionally substituted by one or more radicals R5, where optionally two or more adjacent substituents R4 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
- R5 is selected from the group consisting of H, D, F, an aliphatic hydrocarbon radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 30 C atoms, wherein two or more adjacent substituents R5 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
- m, n, r, u are each, identically or differently, 0, 1, 2 or 3;
- p, t are each, identically or differently, 0 or 1;
- q, v are each, identically or differently, 0, 1, 2, 3 or 4;
- s is 0, 1 or 2.
16 more elements
Dependencies are inferred from the claim text.