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US 9,595,681 B2Granted
Compounds and organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsTeresa Mujica-Fernaud, Elvira Montenegro, Amir Hossain Parham, Arne Buesing, Frank Voges
Life of this patent
Estimating the term…
Abstract
The present invention concerns particular fluorenes, the use of the compound in an electronic device, and an electronic device containing at least one of these compounds. The present invention further concerns a method for producing the compound and a formulation and composition containing one or more of the compounds.
Claims14
An electroluminescent device comprising at least one compound of the general formula (2)
- where the following applies to the symbols and indices used:
- p, q, r, s
- are 0 or 1, where p+q+r+s=1;
- Za0, Zb0, Zc0, Zd0
- are, identically or differently on each occurrence, equal to R4
- Za1, Zb1, Zc1, Zd1 are equal to
- B
- is a single bond, a divalent aryl group having 6 to 30 ring atoms or a divalent heteroaryl group having 5 to 30 ring atoms, each of which is optionally substituted by one or more radicals R6, where, if B is a single bond, the nitrogen atom is bonded directly to the fluorene;
- Ar1 and Ar2 are selected, identically or differently on each occurrence, from the following groups of the formulae (42) to (107), (119)-(121) and (123)-(142)
- where the dashed line denotes the linking position to the nitrogen atom;
- R2, R4, and R5
- are H, D, F, Cl, Br, I, C(═O )R6, CN, Si(R6)3, NO2, N(R6)2, P(═O )(R6)2, S(═O )R6, S(═O )2R6, 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 or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R6 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by —R6C═CR6—, —C≡C—, Si(R6)2, C═O, C═S, C═NR6, —C(═O)O—, —C(═O)NR6—, P(═O)(R6), —O—, —S—, 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, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R6, or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R6;
- R1
- is H, D, F, Cl, Br, I, C(═O)R6, CN, Si(R6)3, NO2, N(R6)2, P(═O)(R6)2, S(═O)R6, S(═O)2R6, a straight-chain alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkoxy or thioalkyl group having 3 to 20 C atoms or an alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R6 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by —R6C═CR6, —C≡C—, Si(R6)2, C═O, C═S, C═NR6, —C(═O)O—, —C(═O)NR6—, P(═O)(R6), —O—, —S—, 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, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R6, or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, where the radicals R1 and R2 cannot be identical and the radicals R3 to R5 may on each occurrence be identical or different, but is optionally identical to either R1or to R2;
- R3 is H;
- R6
- is on each occurrence, identically or differently, H, D, F, Br, I, C(═O)R7, CN, Si(R7)3, NO2, P(═O)(R7)2, S(═O)R7, S(═O)2R7, N(R7)2, 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 or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R7 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by —R7C═CR7—, —C≡C—, Si(R7)2, C═O, C═S, C═NR7, —C(═O)O—, —C(═O)NR7—, P(═O)(R7), —O—, —S—, 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, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R7, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R7, where two or more adjacent substituents R6 may form a mono- or polycyclic ring system with one another;
- R7
- is selected from the group consisting of H, D, F, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 C atoms, in which one or more H atoms is optionally replaced by D or F, where two or more adjacent substituents R7 may form a mono- or polycyclic ring system with one another, and
- wherein the compound of formula (2) is a monoamine compound.
17 more elements
A compound of the general formula (2)
- where the following applies to the symbols and indices used:
- p, q, r, s
- are 0 or 1, where p+q+r+s=1;
- Za0, Zb0, Zc0, Zd0
- are, identically or differently on each occurrence, equal to R4
- Za1,Zb1, Zc1, Zd1 are equal to
- B
- is a single bond, a divalent aryl group having 6 to 30 ring atoms or a divalent heteroaryl group having 5 to 30 ring atoms, each of which is optionally substituted by one or more radicals R6, where, if B is a single bond, the nitrogen atom is bonded directly to the fluorene;
- Ar1 and Ar2 are selected, identically or differently on each occurrence, from the following groups of the formulae (42) to (107) (119)-(121) and (123)-(142)
- where the dashed line denotes the linking position to the nitrogen atom;
- R2 and R4
- are H, D, F, Cl, Br, I, C(═O)R6, CN, Si(R6)3, NO2, N(R6)2, P(═O)(R6)2, S(═O)R6, S(═O)2R6, 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 or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R6 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by —R6C═CR6—, —C≡C—, Si(R6)2, C═O, C═S, C═NR6, —C(═O)O—, —C(═O)NR6—, P(═O)(R6), —O—, —S—, 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, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R6, or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R6,
- and where at least one of the radicals from R1 and R2 represents an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R6;
- R1
- is H, D, F, Cl, Br, I, C(═O)R6, CN, Si(R6)3, NO2, N(R6)2, P(═O)(R6)2, S(═O)R6, S(═O)2R6, a straight-chain alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkoxy or thioalkyl group having 3 to 20 C atoms or an alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R6 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by —R6C═CR6—, —C≡C—, Si(R6)2, C═O, C═S, C═NR6, —C(═O)O—, —C(═O)NR6—, P(═O)(R6), —O—, —S—, 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, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R6, or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, where the radicals R1 and R2 cannot be identical and the radicals R3 to R5 may on each occurrence be identical or different, but is optionally identical to either R1 or to R2;
- R3 is H;
- R5
- is H, D, C(═O)R6, CN, Si(R6)3, NO2, N(R6)2, P(═O)(R6)2, S(═O)R6, S(═O)2R6, 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 or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R6 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by —R6C═CR6—, —C≡C—, Si(R6)2, C═O, C═S, C═NR6, —C(═O)O—, —C(═O)NR6—, P(═O)(R6), —O—, —S—, 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, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R6, or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R6,
- R6
- is on each occurrence, identically or differently, H, D, F, Br, I, C(═O)R7, CN, Si(R7)3, NO2, P(═O)(R7)2, S(═O)R7, S(═O)2R7, N(R7)2, 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 or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R7 and where one or more CH2 groups in the above-mentioned groups is optionally replaced by —R7C═CR7—, —C≡C—, Si(R7)2, C═O, C═S, C═NR7, —C(═O)O—, —C(═O)NR7—, P(═O)(R7), —O—, —S—, 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, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R7, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R7, where two or more adjacent substituents R6 may form a mono- or polycyclic ring system with one another;
- R7
- is selected from the group consisting of H, D, F, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 C atoms, in which one or more H atoms is optionally replaced by D or F, where two or more adjacent substituents R7 may form a mono—or polycyclic ring system with one another;
- and
- wherein the compound of formula (2) is a monoamine compound.
21 more elements
Dependencies are inferred from the claim text.