Back to results
US 10,374,162 B2Granted
Fullerene derivatives
AssigneesMerck Patent GmbH, Nano-C, Inc.
InventorsNicolas Blouin, Stephane Berny, Edward A. Jackson, Henning Richter
Life of this patent
Estimating the term…
Abstract
The invention relates to fullerene derivatives of formula I, to mixtures and formulations containing them, to the use of the fullerene derivatives, mixtures and formulations as organic semiconductors in, or for the preparation of electronic devices, especially organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to electronic devices comprising, or being prepared from, these fullerene derivatives, mixtures or formulations.
Claims30
A compound of formula I
- wherein
- Cn denotes a fullerene composed of n carbon atoms, optionally with one or more atoms trapped inside,
- Adduct is a secondary adduct, or a combination of secondary adducts, appended to the fullerene Cn with any connectivity,
- m is 0, an integer>1, or a non-integer>0,
- o is an integer≥1,
- ArS1 denotes an aryl or heteroaryl group with 5 to 20, preferably 5 to 15, ring atoms, which is mono- or polycyclic,
- R1 to R6 denote, independently of each other, H, halogen, CN, R7, R8 or R9,
- R7 denotes, on each occurrence identically or differently, a saturated or unsaturated, non-aromatic carbo- or heterocyclic group, or an aryl, heteroaryl, aryloxy or heteroaryloxy group, wherein each of the aforementioned groups has 3 to 20 ring atoms, is mono- or polycyclic, does optionally contain fused rings, and is optionally substituted by one or more halogen atoms or CN groups, or by one or more identical or different groups R8 or R9,
- R8 denotes, on each occurrence identically or differently, an alkyl group with 1 to 30 C atoms, which is straight-chain, branched or cyclic, and in which one or more CH2 groups are optionally replaced by —O—, —S—, —C(═O)—, —C(═S)—, —C(═O)—O—, —O—C(═O)—, —NR0—, —C(═O)NR0—, —NR0—C(═O)—, —SiR0R00—, —CF2—, —CHR0═CR00—, —CY1═CY2— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN,
- R9 denotes, on each occurrence identically or differently, a straight-chain, branched or cyclic alkyl group with 1 to 50, preferably 2 to 50, more preferably 2 to 25, most preferably 2 to 12, C atoms, in which one or more CH2 or CH3 groups are replaced by a cationic or anionic group,
- Y1 and Y2 denote, independently of each other, H, F, Cl or CN,
- R0 and R00 denote, independently of each other, H or an optionally substituted carbyl or hydrocarbyl group having 1 to 40 C atoms,
- with the provisos that
- a) at least one of R1, R2, R3 and R4 is different from H, and
- b) if n=70, then R1 is different from —C(═O)—O—CH3 if R2 is H, and R2 is different from —C(═O)—O—CH3 if R1 is H, and
- wherein when R1 , R2, R3 and R4 are different from H, they are selected from the following formulae
- wherein
- ArS2 denotes R7 or has one of the meanings of ArS1,
- i is 0 or an integer from 1 to 9,
- k is 0 or an integer from 1 to 9.
17 more elements
Dependencies are inferred from the claim text.