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US 9,871,213 B2Granted
Organic electroluminescent device
AssigneeMerck Patent GmbH
InventorsPhilipp Stoessel, Esther Breuning, Arne Buesing, Amir Hossain Parham, Holger Heil, Horst Vestweber
Life of this patent
Estimating the term…
Abstract
The present invention relates to the use of aromatic boronic acid or borinic acid derivatives in organic electronic devices, in particular electroluminescent devices.
Claims2
A compound of formulae (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), or (26)
- wherein said compounds of formulae (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), or (26) are optionally substituted by R1, wherein
- B is a boron atom;
- X is, identically or differently on each occurrence, OR2, SR2, N(R2)2, NHR2, or OBAr2;
- Y is, identically or differently on each occurrence, Ar or X;
- R1 is, identically or differently on each occurrence, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkoxy chain having up to 40 C atoms optionally substituted by R3, or a branched or cyclic alkyl, alkoxy, or thioalkoxy chain having 3 to 40 C atoms, optionally substituted by R3, wherein one or more non-adjacent C atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by N—R3, O, S, CO, O—CO—O, CO—O, —CR3═CR3—, or —C≡C—and wherein one or more H atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more R3, or a combination of two, three or four of these systems;
- and wherein two or more R1 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms.
- Ar1 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, which may be substituted by R1;
- G is, identically or differently on each occurrence, C—H, C—R1, C—BXY, or N;
- J is, identically or differently on each occurrence, C—H, C—R1, or C—BXY;
- v is, identically or differently on each occurrence, 0 or 1;
- R2 is, identically or differently on each occurrence, a straight-chain alkyl chain having up to 40 C atoms optionally substituted by R3 or a branched or cyclic alkyl chain having 3 to 40 C atoms optionally substituted by R3;
- wherein one or more non-adjacent C atoms is optionally replaced by N—R3, O, S, CO, O—CO—O, CO—O, —CR3═CR3—, or —C≡C—, with the proviso that a heteroatom is not bonded directly to the oxygen or sulfur or nitrogen of the group X or Y;
- and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R3, or a combination of two, three or four of these systems;
- and wherein two or more radicals R2 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- with the proviso when X is OR2 and Y is OR2 in formulae (24) and (25), the two R2 define an aromatic ring system, and with the proviso that the following compounds are excluded:
13 more elements
A compound of formulae (27), (27a), or (28)
- wherein
- B is a boron atom;
- X is, identically or differently on each occurrence, OR2, SR2, N(R2)2, NHR2, or OBAr2;
- Y is, identically or differently on each occurrence, Ar or X;
- Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more R1;
- Ar1 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, which may be substituted by R1;
- R1 is, identically or differently on each occurrence, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkoxy chain having up to 40 C atoms optionally substituted by R3, or a branched or cyclic alkyl, alkoxy, or thioalkoxy chain having 3 to 40 C atoms, optionally substituted by R3, wherein one or more non-adjacent C atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by N—R3, O, S, CO, O—CO—O,CO—O, —CR3═CR3—, or —C≡C—and wherein one or more H atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more R3, or a combination of two, three or four of these systems;
- and wherein two or more R1 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms.
- v is, identically or differently on each occurrence, 0 or 1;
- Z is, identically or differently on each occurrence, O, S, NR2, or NH;
- L is, identically or differently on each occurrence, an organic group having 4 to 60 C atoms, to which at least four groups Z are bonded in such a way that they are able, with the boron atom, to form a cyclic system;
- R2 is, identically or differently on each occurrence, a straight-chain alkyl chain having up to 40 C atoms optionally substituted by R3 or a branched or cyclic alkyl chain having 3 to 40 C atoms optionally substituted by R3;
- wherein one or more non-adjacent C atoms is optionally replaced by N—R3, O, S, CO, O—CO—O, CO—O, —CR3═CR3—, or —C≡C—with the proviso that a heteroatom is not bonded directly to the oxygen or sulfur or nitrogen of the group X or Y;
- and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R3, or a combination of two, three or four of these systems;
- and wherein two or more radicals R2 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
- Ar2 is, identically or differently on each occurence, a fused aryl or heteroaryl group having 9 to 20 C atoms;
- Ar3 is, identically or differently on each occurence, a flourene or spirobiflourene group optionally substituted by R1;
- Q is, identically or differently on each occurrence, a divalent unit selected from Ar, O, S, SO, SO2, Se, SeO, SeO2, Te, TeO, TeO2, NAr, PAr, P(═O)Ar, AsAr, As(═O)Ar, SbAr, Sb(═O)Ar, C(R1)2, C═O, Si(R1)2, and O—BAr—O;
- p is, identically or differently on each occurrence, 1, 2, 3, 4, 5, or 6;
- is 0 or 1;
- t is 1, 2, 3, 4, or 5;
- w is, identically or differently on each occurrence, 1, 2, 3, 4, 5, or 6;
- with the proviso that Ar2 in formula (27) is not naphthyl on each occurrence if all p equal 1 and at the same time s equals 0 and t equals 1, and with the proviso that boronic acid esters of formula (28) formed with pinacol, 1,2-ethanediol, 2,2-dimethyl-1,3-propanediol, 2,3-butanediol, and isopropanol are excluded.
21 more elements
Dependencies are inferred from the claim text.