Fused bis-aryl fullerene derivatives

Patent metadata

Field	Value
Publication number	US-2017084841-A1
Application number	US-201515119968-A
Country	US
Kind code	A1
Filing date	Mar 5, 2015
Priority date	Mar 31, 2014
Publication date	Mar 23, 2017
Grant date	—

Abstract

The invention relates to novel fullerene derivatives, to methods for their preparation and educts or intermediates used therein, 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 organic electronic (OE) devices, especially organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising, or being prepared from, these fullerene derivatives, mixtures or formulations.

First claim

1 . A compound of formula I

wherein
C n is 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 C n with any connectivity,
m is 0, an integer≧1, or a non-integer>0,
o is an integer≧1,
R 1 , R 2 , denote, independently of each other, H, halogen, CN, R 5 , R 6 or R 7 ,
R 3 , R 4 independently of each other have one of the meanings of R 1 , or form a group Ar S2 together with the cyclohexadiene ring to which they are attached,
R 5 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 R 6 ,
R 6 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 CH 2 groups are optionally replaced by —O—, —S—, —C(═O)—, —C(═S)—, —C(═O)—O—, —O—C(═O)—, —NR 0 —, —C(═O)—NR 0 —, —NR 0 —C(═O)—, —SiR 0 R 00 —, —CF 2 —, —CHR 0 ═CR 00 —, —CY 1 ═CY 2 — 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,
R 7 denotes, on each occurrence identically or differently, a straight-chain, branched or cyclic alkyl group with 1 to 50 C atoms, in which one or more CH 2 or CH 3 groups are replaced by a cationic or anionic group,
Ar S1 , Ar S2 denote, independently of each other, an aryl or heteroaryl group with 5 to 20 ring atoms, which is mono- or polycyclic, and which is substituted by one or more identical or different substituents R 1 or R 2 ,
Y 1 and Y 2 denote, independently of each other, H, F, Cl or CN,
R 0 and R 00 denote, independently of each other, H or an optionally substituted carbyl or hydrocarbyl group with 1 to 40 C atoms,

excluding the following compounds, wherein R is C 1 -C 6 -alkyl and the fullerene is a C 60 fullerene:

2 . The compound of claim 1 , wherein n is 60 or 70.

3 . The compound of claim 1 , wherein C n is a carbon based fullerene or an endohedral fullerene.

4 . The compound of claim 3 , wherein C n is selected from (C 60-lh )[5,6]fullerene, (C 70-D5h )[5,6]fullerene, (C 76-D2 *)[5,6]fullerene, (C 84-D2 *)[5,6]fullerene, (C 84-D2d )[5,6]fullerene, La@C 60 , La@C 82 , Y@C 82 , Sc 3 N@C 80 , Y 3 N@C 80 , Sc 3 C 2 @C 80 or a mixture of two or more of the aforementioned fullerenes.

5 . The compound according to claim 1 , wherein m is 0 and o is 1.

6 . The compound according to claim 1 , wherein the fullerene C n is substituted at a [6,6] and/or [5,6] bond.

7 . The compound according to claim 1 , which is selected from the following subformulae:

wherein n, m, o, Ar S1 , Ar S2 , R 1 and R 2 have the meanings given in claim 1 .

8 . The compound according to claim 1 , wherein Ar S1 and Ar S2 are independently of each other selected from the following groups

which are optionally substituted by one or more groups R 1 , and wherein V is CH or N, and W is independently selected from the group consisting of S, O and Se.

9 . The compound according to claim 1 , wherein Ar S1 and Ar S2 are selected from the following groups

which are optionally substituted by one or more groups R 1 .

10 . The compound according to claim 1 , wherein R 1 and R 2 are independently of each other selected from H, straight-chain branched or cyclic alkyl with 1 to 30 C atoms, —O—, —COOR 000 , —COR 000 , CONR 0 R 000 , —F, —Cl, —NR 0 R 000 , wherein R 000 has one of the meanings of R 00 in claim 1 different from H.

11 . The compound according to claim 1 , wherein R 1 and R 2 are selected from alkyl, fluoroalkyl, alkoxy, thioalkyl, —COO-alkyl and —CO-alkyl having 1 to 30 C atoms.

12 . The compound according to claim 1 , wherein one or more of R 1 , R 2 , R 3 and R 4 denote R 7 , wherein R 7 is a straight-chain, branched or cyclic alkyl group with 1 to 50 C atoms, in which one or more CH 2 or CH 3 groups are replaced by a cationic or anionic group.

13 . The compound according to claim 1 , which is selected from the following subformulae:

wherein R 1 R 2 and C n are as defined in claim 1 .

14 . An electron acceptor or n-type semiconductor in a semiconducting material, organic electronic device or component of an organic electronic device, which comprises a compound of claim 1 .

15 . A composition comprising two or more fullerene derivatives, one or more of which is a compound of claim 1 .

16 . A composition comprising one or more compounds of claim 1 as electron acceptor or n-type semiconductor component, and further comprising one or more semiconducting compounds which have electron donor or p-type properties.

17 . A composition comprising one or more compounds of claim 1 and one or more p-type organic semiconductor compounds selected from conjugated organic polymers.

18 . A composition comprising one or more compounds of claim 1 and one or more compounds which are selected from compounds having one or more of a semiconducting, charge transport, hole transport, electron transport, hole blocking, electron blocking, electrically conducting, photoconducting, photoactive and light emitting property.

19 . A semiconducting, charge transport, electrically conducting, photoconducting, photoactive thermoelectric material or light emitting material, or an organic electronic (OE) device, or a component of such an OE device or an assembly comprising such an OE device or such a component, which comprises a compound of claim 1 .

20 . A semiconducting, charge transport, electrically conducting, photoconducting, photoactive, thermoelectric or light emitting material, which comprises a compound of claim 1 .

21 . A formulation comprising one or more compounds of claim 1 , and further comprising one or more organic solvents.

22 . An OE device, or a component thereof, or an assembly comprising the OE device, which is prepared using a formulation of claim 21 .

23 . An OE device, or a component thereof, or an assembly comprising the OE device, which comprises a compound of claim 1 .

24 . The OE device, or a component thereof, or an assembly comprising the OE device according to claim 22 , wherein the device is an optical, electrooptical, electronic, electroluminescent, photoluminescent, photoactive or thermoelectric device.

25 . The OE d

Assignees

• Merck Patent Gmbh
• Nano-C Inc

Inventors

• Blouin Nicolas
• Berny Stephane
• Jackson Edward A
• Richter Henning

Classifications

• C07C2604/00

  Fullerenes, e.g. C60 buckminsterfullerene or C70 · CPC title

• C07C43/21 Primary

  containing rings other than six-membered aromatic rings · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/215

  comprising substituents, e.g. PCBM · CPC title