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US 8,852,756 B2Granted
Materials for organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsHorst Vestweber, Holger Heil, Philipp Stoessel, Arne Buesing, Amir Hossain Parham, Rocco Fortte
Life of this patent
Estimating the term…
Abstract
The present invention relates to the improvement of organic electroluminescent devices, in particular blue-emitting devices, by using compounds of the formula (1) as dopants in the emitting layer.
Claims21
A compound of the formula (1)
- wherein
- Y and Z are, identically or differently, N, P, P═O, PF2, P═S, As, As═O, As═S, Sb, Sb═O, Sb═S, C═O, O, S, Se, Te, S═O, SO2, Se═O, SeO2, Te═O or TeO2;
- Ar1, Ar2 and Ar3 are on each occurrence, identically or differently, a benzene, or pyridine;
- Ar4, Ar5, Ar6 and Ar7 are on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R1;
- E is on each occurrence, identically or differently, a single bond, N(R1), O,S, C(R1)2, Si(R1)2 or B(R1);
- R1 is on each occurrence, identically or differently, H, F, CN, NO2, 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, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is 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 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 40 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R1, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R1, or a combination of these systems;
- two or more substituents R1 optionally form a mono- or polycyclic ring system with one another;
- R2 is on each occurrence, identically or differently, H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 C atoms;
- X1 and X4 are on each occurrence, identically or differently, a bridge which, with Ar1 and Ar2, defines a cyclic system selected from C(R1)2, Si(R1)2, C═O, C═NR1, C═C(R1)2, O,S, S═O, SO2, N(R1), P(R1), P(═O)R1, P(═S)R1, B(R1) or a combination of two, three or four of these groups;
- X2 and X3 are on each occurrence, identically or differently, a bridge which, with Ar2 and Ar3, defines a cyclic ring system 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), P(═O)R1, P(═S)R1 or a combination of two, three or four of these groups;
- p=0;
- one of the two indices n and o is equal to 1, and the other of the two indices n and o is equal to 0;
- q and r are on each occurrence 1 if the corresponding central atom of the group Y or Z is an element from the 5th main group and on each occurrence are equal to 0 if the corresponding central atom of the group Y or Z is an element from the 4th or 6th main group;
- s is 1, 2 or 3;
- and
- t is on each occurrence, identically or differently, 0 or 1, where t=0 means that R1 radicals are bonded instead of the group E;
- furthermore, t=0 if q=0 and t=0, if r=0.
14 more elements
A compound selected from structures (1) to (104)
A conjugated, partially conjugated or non-conjugated polymer, oligomer or dendrimer comprising one or more compounds of the formula (1b)
- wherein
- Y and Z are, identically or differently, N, P, P═O, PF2, P═S, As, As═O, As═S, Sb, Sb═O, Sb═S, C═O, O, S, Se, Te, S═O, SO2, Se═O, SeO2, Te═O or TeO2;
- Ar4, Ar5, Ar6 and Ar7 are on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R1;
- E is on each occurrence, identically or differently, a single bond, N(R1), O, S, C(R1)2, Si(R1)2 or B(R1);
- R1 is on each occurrence, identically or differently, H, F, Cl, Br, I, CN, NO2, Si(R2)3, B(OR2)2, 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 is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is 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 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 40 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R1, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R1, or a combination of these systems;
- two or more substituents R1 optionally form a mono- or polycyclic ring system with one another;
- R2 is on each occurrence, identically or differently, H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 C atoms;
- X1 are on each occurrence, identically or differently, a bridge which, with Ar1 and Ar2, defines a cyclic system selected from C(R1)2, Si(R1)2, C═O, C═NR1, C═C(R1)2, O, S, S═O, SO2, N(R1), P(R1), P(═O)R1, P(═S)R1, B(R1) or a combination of two, three or four of these groups;
- X2 are on each occurrence, identically or differently, a bridge which, with Ar2 and Ar3, defines a cyclic ring system 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), P(═O)R1, P(═S)R1 or a combination of two, three or four of these groups;
- q and r are on each occurrence 1 if the corresponding central atom of the group Y or Z is an element from the 5th main group and on each occurrence are equal to 0 if the corresponding central atom of the group Y or Z is an element from the 4th or 6th main group;
- s is 1, 2 or 3;
- and
- t is on each occurrence, identically or differently, 0 or 1, where t=0 means that R1 radicals are bonded instead of the group E;
- furthermore, t=0 if q=0 and t=0, if r=0,
- wherein one or more radicals R1 in the compound of the formula (1b) represent a bond to the polymer, oligomer or dendrimer.
12 more elements
Dependencies are inferred from the claim text.