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US 9,312,495 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsChristof Pflumm, Amir Hossain Parham, Constanze Brocke, Elvira Montenegro, Frank Voges, Holger Heil, Arne Buesing
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.
Claims21
A compound of the formula (1),
- where the following applies to the symbols and indices used:
- Ar is, identically or differently on each occurrence, an aromatic ring system selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, each of which is optionally substituted by one or more radicals R1;
- Ar1 and Ar2 are, identically or differently on each occurrence, selected from the groups of the formulae (5) to (28),
- where the dashed bond indicates the position of the bond to the nitrogen;
- R is on each occurrence, identically or differently, and are H, D, F, Cl, Br, I, CN, Si(R2)3, 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, each of which is optionally substituted by one or more radicals R2, where in each case one or more non-adjacent CH2 groups is optionally replaced by Si(R2)2, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 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 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, which may in each case be substituted by one or more radicals R2, or a combination of two, three, four or five of these groups, which may in each case be identical or different, an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, where two or more adjacent substituents R or two or more adjacent substituents R1 may optionally form a mono- or polycyclic, aliphatic ring system, which is optionally substituted by one or more radicals R2;
- R1 are on each occurrence, identically or differently, and are H, D, F, CN, a straight-chain alkyl having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, or an aromatic or heteroaromatic ring system having 6 to 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, dibenzofuran and dibenzothiophene, or a combination of two, three, four or five of these groups, which may in each case be identical or different;
- R2 is on each occurrence, identically or differently, is H, D, F, Cl, Br, I, Si(R3)3, 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, each of which is optionally substituted by one or more radicals R3, where one or more non-adjacent CH2 groups is optionally replaced by Si(R3)2, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms is optionally replaced by D, F, Cl, Br or I, an aromatic ring system having 6 to 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene or a combination of two, three, four or five of these groups, which may in each case be identical or different, which may in each case be substituted by one or more radicals R3, an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, or an aralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, where two or more adjacent substituents R2 may optionally form a mono- or polycyclic, aliphatic ring system, which is optionally substituted by one or more radicals R3;
- R3 is selected from the group consisting of H, D, F, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic ring system having 6 to 30 C atoms, in which one or more H atoms is optionally replaced by D or F, where two or more adjacent substituents R3 may form a mono- or polycyclic, aliphatic ring system with one another;
- m is 0, 1, 2 or 3;
- n is on each occurrence, identically or differently, 0, 1, 2, 3 or 4;
- p is 0, 1 or 2;
- the following compounds are excluded from the invention:
9 more elements
A compound of the formula (1),
- where the following applies to the symbols and indices used:
- Ar is, identically or differently on each occurrence, an aromatic ring system selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, each of which is optionally substituted by one or more radicals R1;
- the group —NAr1Ar2 has the structure of one of the formulae (29), (30), (31) or (32) or in that the group —Ar—NAr1Ar2 has the structure of one of the formulae (33), (34), (35) or (36),
- and the dashed bond indicates the bond to the spirobifluorene or to Ar;
- and the dashed bond indicates the bond to the spirobifluorene;
- where
- R is on each occurrence, identically or differently, and are H, D, F, Cl, Br, I, CN, Si(R2)3, 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, each of which is optionally substituted by one or more radicals R2, where in each case one or more non-adjacent CH, groups is optionally replaced by Si(R2)2, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 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 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, which may in each case be substituted by one or more radicals R2, or a combination of two, three, four or five of these groups, which may in each case be identical or different, an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, where two or more adjacent substituents R or two or more adjacent substituents R1 may optionally form a mono- or polycyclic, aliphatic ring system, which is optionally substituted by one or more radicals R2;
- R1 are on each occurrence, identically or differently, and are H, D, F, CN, a straight-chain alkyl having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, or an aromatic or heteroaromatic ring system having 6 to 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, dibenzofuran and dibenzothiophene, or a combination of two, three, four or five of these groups, which may in each case be identical or different;
- R2 is on each occurrence, identically or differently, is H, D, F, Cl, Br, I, Si(R3)3, 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, each of which is optionally substituted by one or more radicals R3, where one or more non-adjacent CH2 groups is optionally replaced by Si(R3)2, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms is optionally replaced by D, F, Cl, Br or I, an aromatic ring system having 6 to 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene or a combination of two, three, four or five of these groups, which may in each case be identical or different, which may in each case be substituted by one or more radicals R3, an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, or an aralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, where two or more adjacent substituents R2 may optionally form a mono- or polycyclic, aliphatic ring system, which is optionally substituted by one or more radicals R3;
- R3 is selected from the group consisting of H, D, F, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic ring system having 6 to 30 C atoms, in which one or more H atoms is optionally replaced by D or F, where two or more adjacent substituents R3 may form a mono- or polycyclic, aliphatic ring system with one another;
- m is 0, 1, 2 or 3;
- n is on each occurrence, identically or differently, 0, 1, 2, 3 or 4;
- p is 0, 1 or 2;
- and
- the following compounds are excluded from the invention:
12 more elements
Dependencies are inferred from the claim text.