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US 9,126,970 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsChristof Pflumm, Arne Buesing, Amir Hossain Parham, Teresa Mujica-Fernaud, Holger Heil, Philipp Stoessel
Life of this patent
Estimating the term…
Abstract
The present invention describes indenocarbazole derivatives having electron- and hole-transporting properties, in particular for use in the emission and/or charge-transport layer of electroluminescent devices or as matrix material. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to electronic devices comprising same.
Claims15
A compound of formula (1) or formula (1′):
- wherein
- Y is C if a group X2 is bonded to the group Y, or is on each occurrence, identically or differently, CR or N if no group X2 is bonded to the group Y;
- E is on each occurrence, identically or differently, a covalent single bond or a divalent bridge selected from N(R1), B(R1), C(R1)2, O, Si(R1)2, C═NR1, C═C(R1)2, S, S═O, SO2, P(R1) and P(═O)R1;
- X1 is on each occurrence, identically or differently, a divalent bridge selected from N(R11), Si(R1)2, P(R1) and P(═O)R;
- X2 is on each occurrence, identically or differently, a divalent bridge selected from B(R1), C(R1)2, Si(R1)2, P(R1) and P(═O)R1;
- X3 is on each occurrence, identically or differently, a divalent bridge selected from N, B, C(R1), Si(R1), P and P(═O);
- L is a divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R1;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system optionally substituted by one or more radicals R1;
- m is 0;
- n is 1;
- q is 1, 2, 3, 4, 5 or 6;
- R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(Ar)2, C(═O)Ar, P(═O)Ar2, S(═O)Ar, S(═O)2Ar, CR2═CR2Ar, CN, NO2, Si(R2)3, B(OR2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R2, wherein 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, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aryl or heteroaryl group having 5 to 40 ring atoms, which in each case are optionally substituted by one or more radicals R2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case be are optionally substituted by one or ore radicals R2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R2, or a combination of these systems;
- and wherein two or more substituents R, together with the atoms to which they are bonded, optionally define a mono- or polycyclic aliphatic or aromatic ring system with one another or, if they are bonded to Ar, with Ar;
- R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, NO2, CF3, B(OR2)2, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or 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 R2, wherein 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, C═NR2, —O—, —S—, —COO— or —CONR2— and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN or NO2, or arylamines, or substituted or unsubstituted carbazoles, which in each case are optionally substituted by one or more radicals R2, or an aryl or heteroaryl group having 5 to 40 ring atoms, which are optionally substituted by one or more aromatic, heteroaromatic or non-aromatic radicals R2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of these systems;
- and wherein two or more substituents R1 optionally define a mono- or polycyclic aliphatic or aromatic ring system with one another together with the atoms to which they are bonded;
- R11 is a heteroaryl group having 5 to 40 ring atoms, which may be substituted by one or more aromatic, heteroaromatic or non-aromatic radicals R2, or a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R2;
- R2 is on each occurrence, identically or differently, H, D or an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aryl or heteroaryl group having 5 to 40 ring atoms, or a combination of these groups;
- and
- with the proviso that when
- when X1 is N(R11) then X2 is for C(R1)2
- and
- wherein the following compound is excluded:
19 more elements
A compound selected from the group consisting of compounds of formulae (3g) to (3n):
- wherein
- X2 is on each occurrence, identically or differently, a divalent bridge selected from N(R1), B(R1), Si(R1)2, C═O, C═NR1, C═C(R1)2, S, S═O, SO2, CR1—CR1, P(R1) and P(═O)R1;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system optionally substituted by one or more radicals R1;
- R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(Ar)2, C(═O)Ar, P(═O)Ar2, S(═O)Ar, S(═O)2Ar, CR2═CR2Ar, CN, NO2, Si(R2)3, B(OR2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R2, wherein 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, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aryl or heteroaryl group having 5 to 40 ring atoms, which in each case are optionally substituted by one or more radicals R2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case be are optionally substituted by one or ore radicals R2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R2, or a combination of these systems;
- and wherein two or more substituents R, together with the atoms to which they are bonded, optionally define a mono- or polycyclic aliphatic or aromatic ring system with one another or, if they are bonded to Ar, with Ar;
- R1 is on each occurrence, identically or differently is a heteroaryl group having 5 to 40 ring atoms, which may be substituted by one or more aromatic, heteroaromatic or non-aromatic radicals R2, or a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R2;
- and
- R2 is on each occurrence, identically or differently, H, D or an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aryl or heteroaryl group having 5 to 40 ring atoms, or a combination of these groups.
5 more elements
Dependencies are inferred from the claim text.