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US 9,040,172 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsAmir Hossain Parham, Christof Pflumm, Teresa Mujica-Fernaud, Arne Buesing, Holger Heil
Life of this patent
Estimating the term…
Abstract
The present invention describes novel indenofluorene derivatives which can preferably be employed as matrix materials for phosphorescent dopants or as electron-transport materials, in particular for use in the emission and/or charge-transport layer of electroluminescent devices. The invention furthermore relates to polymers which comprise these compounds as structural units and to a process for the preparation of the compounds according to the invention and to electronic devices which comprise same.
Claims16
A compound of formula (I):
- wherein
- W is, identically or differently on each occurrence, N or CR1;
- Y is, identically or differently on each occurrence, N or CR2;
- E is either a single covalent bond or a divalent unit selected from the group consisting of N(R3), C(R3)2, Si(R3)2, C═O, C═NR3, C═C(R3)2, S, S═O, SO2, P(R3) and P(═O)R3;
- X is, identically or differently on each occurrence, a divalent unit selected from the group consisting of C(R3)2, N(R3), Si(R3)2, C═O, C═NR3, C═C(R3)2, S, O, S═O, SO2, P(R3) and P(═O)R3, with the proviso that, if E is a single covalent bond, X is a divalent unit selected from the group consisting of C(R3)2, Si(R3)2, C═O, C═NR3, C═C(R3)2, S, O, S═O, SO2, P(R3) and P(═O)R3;
- n and m
- are, independently of one another, 0 or 1, with the proviso that the sum of n and m is equal to 1 or 2;
- Ar is a divalent or trivalent, mono- or polycyclic aromatic or heteroaromatic unit having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R4a;
- Ar1 is a mono- or polycyclic heteroaromatic group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R4b;
- L is either a single covalent bond or represents a divalent unit selected from the group consisting of —C(O)—, —Ar2—C(O)— and —Ar2—, where, in the case where the divalent unit is —Ar2—C(O)—, the group Ar2 is bonded to N and C(O) is bonded to the group Ar1;
- Ar2 is a divalent mono- or polycyclic aromatic or heteroaromatic unit having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R4a or R4b;
- R1 and R2
- are selected, identically or differently on each occurrence, from the group consisting of H, D, F, Cl, Br, I, N(Ar3)2, C(═O)Ar3, P(═O)(Ar3)2, S(═O)Ar3, S(═O)2Ar3, CN, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R5 and where in each case one or more non-adjacent CH2 groups are optionally replaced by R5C═CR5, C≡C, C═O, C═S, P(═O)(R5), SO, SO2, NR5, O, S, or CONR5 and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO2, or a mono- or polycyclic aromatic ring system having 5 to 40 aromatic ring atoms, which in each case are optionally substituted by one or more radicals R6, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R5, or a combination of these systems;
- wherein two or more adjacent substituents R1 and/or R2 are optionally linked to one another via a single covalent bond or a divalent group Z;
- R3 is selected, identically or differently on each occurrence, from the group consisting of H, D, F, Cl, Br, I, N(Ar3)2, C(═O)Ar3, P(═O)(Ar3)2, S(═O)Ar3, S(═O)2Ar3, CR5═CR5Ar3, CN, NO2, Si(R5)3, B(OR5)2, OSO2R5, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R5 and where in each case one or more non-adjacent CH2 groups is optionally replaced by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, 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, I, CN, or NO2, or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R6, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R5, or a combination of these systems;
- wherein two or more adjacent substituents R3 are optionally linked to one another via a single covalent bond or a divalent group Z;
- R4a
- is selected, from the group consisting of D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R5 and where in each case one or more non-adjacent CH2 groups is optionally replaced by R5C═CR5, C≡C, C═O, C═S, 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, I, CN or NO2, or a mono- or polycyclic aromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R6, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R5, or a combination of these systems;
- wherein two or more adjacent substituents R4a or R4b are optionally linked to one another via a single covalent bond or a divalent group Z;
- R4b
- is selected from the group consisting of D, F, Cl, Br, I, N(Ar3)2, C(═O)Ar3, P(═O)(Ar3)2, S(═O)Ar3, S(═O)2Ar3, CN, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R5 and where in each case one or more non-adjacent CH2 groups is optionally replaced by R5C═CR5, C≡C, C═C, C═O, C═S, 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, I, CN or NO2, or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R6, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R5, or a combination of these systems;
- wherein two or more adjacent substituents R4a or R4b are optionally linked to one another via a single covalent bond or a divalent group Z;
- Ar3 is a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R6;
- R5 is, identically or differently on each occurrence, H, D, a straight-chain alkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups are optionally replaced by NH, O or S and where one or more H atoms are optionally replaced by F, or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R6;
- wherein two or more substituents R5 are optionally linked to one another via a single covalent bond or a divalent group Z;
- R6 is, identically or differently on each occurrence, H, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups are optionally replaced by NH, O or S and where one or more H atoms are optionally replaced by F;
- wherein two or more substituents R6 are optionally linked to one another via a single covalent bond or a divalent group Z;
- Z is a divalent group —(CH2)q—, wherein q is equal to 1, 2, 3, 4, or 5.
25 more elements
Dependencies are inferred from the claim text.