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US 8,986,852 B2Granted
Benzanthracene derivatives for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsPhilipp Stoessel, Arne Buesing, Holger Heil
Life of this patent
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Abstract
The present invention relates to the compounds of the formula (1) and to organic electroluminescent devices, in particular blue-emitting devices, in which these compounds are used as host material or dopant in the emitting layer and/or as hole-transport material and/or as electron-transport material.
Claims17
An uncharged compound of the formula (1)
- wherein the group Ar or Y is bonded via one of positions 2, 3, 4, 5 or 6 of the benz[a]anthracene and correspondingly no radical R is bonded at this position and where the following applies to the symbols and indices:
- Ar is on each occurrence, identically or differently, a divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R;
- Y is a selected from the formula (25)-(31)
- wherein
- R is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(Ar1)2, N(R1)2, C(═O)Ar1, P(Ar1)2, P(═O)(Ar1)2, S(═O)Ar1, S(═O)2Ar1, CR1═CR1Ar1, CN, NO2, Si(R1)3, B(OAr1)2, B(OR1)2, OSO2R1, OH, a straight-chain alkyl or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkoxy group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more non-adjacent CH2 groups is optionally replaced by R1C═CR1, C≡C, 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 or CONR1 and where one or more H atoms is optionally replaced by F, Cl, Br, I, CN or NO2, 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 R, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R, or a combination of these systems;
- two or more adjacent substituents R here optionally form a mono- or polycyclic aliphatic ring system with one another;
- wherein R in positions 7 and 12 of the benzanthracene is hydrogen;
- Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R;
- two radicals Ar1 which are bonded to the same nitrogen or phosphorus atom is optionally linked to one another here by a single bond or by a bridge selected from B(R1), C(R1)2, Si(R1)2, C═O, C═NR1, C═C(R1)2, O, S, S═O, SO2, N(R1), P(R1) and P(═O)R1;
- R1 is on each occurrence, identically or differently, H or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F;
- two or more adjacent substituents R1 here optionally form a mono- or polycyclic aliphatic or aromatic ring system with one another;
- Ar2 is an aryl or heteroaryl group having 5 to 16 aromatic ring atoms, each of which is optionally substituted by one or more radicals R1, or in formula (25) a group of the formula (32) or (33)
- Ar3 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 20 aromatic ring atoms or a triarylamine group having 15 to 30 aromatic ring atoms, each of which is optionally substituted by one or more radicals R1;
- E stands for a single bond, O, S, N(R1) or C(R1)2, where the two radicals R1 optionally forms a Spiro system through ring formation;
- q is 1, 2 or 3;
- s is on each occurrence, identically or differently, 0 or 1;
- m is on each occurrence, identically or differently 0 or 1;
- and
- n is 0;
- p is 0.
17 more elements
A compound of the formula (34)
- wherein
- R is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(Ar1)2, N(R1)2, C(═O)Ar1, P(Ar1)2, P(═O)(Ar1)2, S(═O)Ar1, S(═O)2Ar1, CR1═CR1Ar1, CN, NO2, Si(R1)3, B(OAr1)2, B(OR1)2, OSO2R1, OH, a straight-chain alkyl or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkoxy group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more non-adjacent CH2 groups is optionally replaced by R1C═CR1, C≡C, 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 or CONR1 and where one or more H atoms is optionally replaced by F, Cl, Br, I, CN or NO2, 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 R, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R, or a combination of these systems;
- two or more adjacent substituents R here optionally form a mono- or polycyclic aliphatic ring system with one another;
- Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R;
- two radicals Ar1 which are bonded to the same nitrogen or phosphorus atom is optionally linked to one another here by a single bond or by a bridge selected from B(R1), C(R1)2, Si(R1)2, CO═O, C═NR1, C═C(R1)2, O, S, S═O, SO2, N(R1), P(R1) and P(═O)R1;
- R1 is on each occurrence, identically or differently, H or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F;
- two or more adjacent substituents R1 here optionally form a mono- or polycyclic aliphatic or aromatic ring system with one another;
- and R2 is bonded in position 2, 3, 4, 5 or 6 of the benz[a]anthracene and correspondingly no group R is bonded at this position, and furthermore:
- R2 stands for B(OR1)2 or B(OAr1)2.
6 more elements
Dependencies are inferred from the claim text.