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US 2016/0260911 A1Published application
Materials for electronic devices
AssigneeMerck Patent GmbH
InventorsPhilipp Stoessel, Arne Buesing, Dominik Joosten
Life of this patent
Estimating the term…
Abstract
The present invention relates to an electronic device comprising anode, cathode and at least one organic layer which comprises a compound of the formula (I) to (IV). The invention furthermore encompasses the use of compounds of the formula (I) to (IV) in an electronic device and to a compound of the formula (Ic) to (IVc).
Claims21
1-15. (canceled)
An electronic device comprising anode, cathode and at least one organic layer, wherein the organic layer comprises at least one compound of the following formulae (I) to (IV)
- where the following applies to the symbols occurring:
- X is a single bond;
- L is a divalent, or in the case of k=3, 4, 5 or 6 a tri-, tetra-, penta- or hexavalent group respectively, selected from C═O, C═NR1, Si(R1)2, P(═O)(R1), SO, SO2, alkylene groups having 1 to 20 C atoms, alkenylene or alkynylene groups having 2 to 20 C atoms, where, in the case of the groups mentioned, one or more CH2 groups is optionally replaced by Si(R1)2, O, S, C═O, C═NR1, C═O—O, C═O—NR1, NR1, P(═O)(R1), SO or SO2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO2, aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R1, and any desired combinations of 1, 2, 3, 4 or 5 identical or different groups selected from the above-mentioned groups;
- or L is a single bond, where k in this case must be equal to 2;
- R0 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R1, OSO2R1, COOR1, CON(R1)2, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R1 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, —O—, —S—, —COO— or —CONR1— and where one or more H atoms in the above-mentioned groups 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 R1, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R1, or a combination of these systems, furthermore, two or more adjacent radicals R0 is optionally linked to one another here and form an aliphatic or aromatic ring, or a radical R0 is optionally linked to an adjacent radical R via a single bond or a divalent group Y and form an aliphatic or aromatic ring;
- R is equal to C(═O)R1, OSO2R1, COOR1, CON(R1)2, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R1 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, —O—, —S—, —COO— or —CONR1— and where one or more H atoms in the above-mentioned groups 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 R1, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R1, or a combination of these systems, where furthermore the radical R is optionally linked to one or more adjacent radicals R0 via a single bond or a divalent group Y;
- Y is on each occurrence, identically or differently, a divalent group selected from C═O, C═S, C═NR1, C(R1)2, Si(R1)2, NR1, PR1, P(═O)R1, O, S, SO and SO2;
- R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, CN, NO2, Si(R2)3, B(OR2)2, OSO2R2, OH, COOR2, CON(R2)2, 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R2 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by 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—, —COO— or —CONR2— and where one or more H atoms in the above-mentioned groups 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of these systems, where two or more radicals R1 is optionally linked to one another and may form an aliphatic or aromatic ring;
- R2 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F;
- two or more substituents R2 here may also be linked to one another and form an aliphatic or aromatic ring;
- and
- k is equal to 2, 3, 4, 5 or 6.
9 more elements
A compound of one of the formulae (Ic) to (IVc)
- wherein
- Ar1 and Ar2 are, identically or differently, an aryl group containing 6 to 60 aromatic ring atoms or a heteroaryl group containing 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R1;
- and
- R is an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, or an aralkyl or heteroaralkyl group having 5 to 20 aromatic ring atoms, may be substituted by one or more radicals R1, where the radical R may furthermore be linked to an adjacent group Ar1 or Ar2 via a single bond or via a divalent group Y;
- X is a single bond;
- L is a divalent, or in the case of k=3, 4, 5 or 6 a tri-, tetra-, penta- or hexavalent group respectively, selected from C═O, C═NR1, Si(R1)2, P(═O)(R1), SO, SO2, alkylene groups having 1 to 20 C atoms, alkenylene or alkynylene groups having 2 to 20 C atoms, where, in the case of the groups mentioned, one or more CH2 groups is optionally replaced by Si(R1)2, O, S, C═O, C═NR1, C═O—O, C═O—NR1, NR1, P(═O)(R1), SO or SO2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO2, aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R1, and any desired combinations of 1, 2, 3, 4 or 5 identical or different groups selected from the above-mentioned groups;
- or L is a single bond, where k in this case must be equal to 2;
- Y is on each occurrence, identically or differently, a divalent group selected from C═O, C═S, C═NR1, C(R1)2, Si(R1)2, NR1, PR1, P(═O)R1, O, S, SO and SO2;
- R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, CN, NO2, Si(R2)3, B(OR2)2, OSO2R2, OH, COOR2, CON(R2)2, 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R2 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by 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—, —COO— or —CONR2— and where one or more H atoms in the above-mentioned groups 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of these systems, where two or more radicals R1 is optionally linked to one another and may form an aliphatic or aromatic ring;
- R2 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F;
- two or more substituents R2 here may also be linked to one another and form an aliphatic or aromatic ring;
- and
- k is equal to 2, 3, 4, 5 or 6.
10 more elements
Dependencies are inferred from the claim text.