# US 2013/0157403 A1 · Compounds for photovoltaics

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- Number: US 2013/0157403 A1
- Document ID: US20130157403A1
- Status: Published application
- Kind: A1
- Application number: 13/820,508
- Filed: 2011-09-02
- Published: 2013-06-20
- Earliest claimed: 2010-09-03
- Assignees: Cambridge Display Technology Limited
- Inventors: Sheena Zuberi; Tania Zuberi
- Web page: https://patentgrep.com/patent/US20130157403A1

## CPC

- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers
- H10K 71/135: {using ink-jet printing}
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/151: {Copolymers}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
- C08G 2261/91: Photovoltaic applications
- C08L 2205/02: containing two or more polymers of the same C08L -group
- H10K 85/611: {Charge transfer complexes}
- H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A species for use, for example, in a charge transfer layer of a photovoltaic device, the species comprising an acceptor group to which is fused a tuning group. The species can be a small molecule, polymer or oligomer, and monomers for producing said polymer, photovoltaic devices comprising said species, and methods for producing said device, are also provided.

## Claims

### Claim 1

A species for use in a charge transfer layer of a photovoltaic device, the species comprising an acceptor group, wherein a tuning group is fused to the acceptor group.

### Claim 2 (depends on 1)

A species according to claim 1, wherein the acceptor group comprises at least one acceptor conjugated ring structure.

### Claim 3 (depends on 1)

A species according to claim 1, wherein the tuning group comprises at least one donor conjugated ring structure.

### Claim 4 (depends on 1)

A species according to claim 1, wherein the tuning group has a HOMO level, in isolation from the acceptor group, of at least 4.5 eV.

### Claim 5 (depends on 2)

A species according to claim 2, wherein the or an acceptor conjugated ring structure is fused to one or more tuning groups.

### Claim 6 (depends on 1)

A species according to claim 1, wherein the acceptor group comprises a structure selected from the group consisting of:
where X is S or O and where R1 and R2 are the same or different and comprise H or optionally substituted, straight, branched or cyclic alkyl or alkenyl chains with 1 to 20 carbon atoms, alkoxy, amino, amide, silyl, alkyl silyl or acyl groups, and where Y comprises halogen, nitrile or any electron withdrawing group (EWG).

### Claim 7 (depends on 1)

A species according to claim 1, wherein the tuning group comprises at least one thiophene ring.

### Claim 8 (depends on 7)

A species according to claim 7, wherein the thiophene ring is fused directly to the acceptor group or is fused to the acceptor group via one or more conjugated ring structures.

### Claim 9 (depends on 7)

A species according to claim 7, wherein the tuning group comprises two or more conjugated ring structures of which at least one is a thiophene ring.

### Claim 10 (depends on 7)

A species according to claim 7, wherein the tuning groups comprise a structure selected from the group consisting of:
and diastereoisomers thereof, where R1 comprises H or optionally substituted, straight, branched or cyclic alkyl or alkenyl chains with 1 to 20 carbon atoms, alkoxy, amino, amide, silyl, alkyl silyl or acyl groups.

### Claim 11 (depends on 1)

A species according to claim 1, wherein the tuning group is substituted at one or more available carbons.

### Claim 12 (depends on 11)

A species according to claim 11, wherein the tuning group is substituted by one or more groups, which may be the same or different, selected from the group consisting of optionally substituted straight branched or cyclic alkyl or alkenyl chains with 1 to 20 carbon atoms, alkoxy amino, amide, silyl, alkenyl, alkyl and alkyl silyl.

### Claim 13 (depends on 1)

A species according to claim 1, wherein the acceptor group is substituted at one or more available carbon atom.

### Claim 14 (depends on 1)

A species according to any of claim 1 comprising a structure selected from the group consisting of:
where X is S or O, where Y is F, CN or another electron withdrawing group and R3 to R26 are the same or different and comprise C1 to C20 optionally substituted, straight, branched or cyclic alkyl, alkenyl, alkynyl, aromatic, alkoxy, amino or amido groups.

### Claim 15 (depends on 1)

A species according to claim 1 where the species is a small molecule.

### Claim 16 (depends on 15)

A species according to claim 15 wherein the small molecule further comprises solvating groups.

### Claim 17 (depends on 1)

A species according to any of claim 1, wherein the species comprises a polymeric species.

### Claim 18 (depends on 17)

A species according to claim 17, wherein at least part of one or both of the tuning group and the acceptor group lie in the polymer backbone.

### Claim 19 (depends on 17)

A species according to claim 17, wherein the species is a copolymeric species.

### Claim 20 (depends on 19)

A species according to claim 19, wherein the copolymer comprises between 30 mol % and 70 mol % fluorene residues.

### Claim 21

A monomeric species comprising a residue comprising an acceptor group, wherein a tuning group is fused to the acceptor group, the species substituted with two or more reactive groups.

### Claim 22 (depends on 21)

A monomeric species according to claim 21, wherein the reactive groups comprise halogens and/or boronic esters.

### Claim 23 (depends on 21)

A monomeric species according to claim 21, wherein the reactive groups comprise halogens and/or organotin groups.

### Claim 24

A polymer for use in a charge transfer layer of a photovoltaic device, the polymer comprising a first repeat unit comprising an acceptor group, wherein a tuning group is fused to the acceptor group.

### Claim 25 (depends on 24)

A polymer according to claim 24, further comprising a second repeat unit comprising a fluorene residue.

### Claim 26 (depends on 25)

A polymer according to claim 25, wherein the molar ratio of first repeat unit to second repeat unit is between 30%:70% and 70%:30%.

### Claim 27 (depends on 25)

A polymer according to claim 25 comprising a third repeat unit and optionally a fourth and/or fifth and/or sixth repeat unit.

### Claim 28 (depends on 1)

A solution for forming a change transfer layer of a photovoltaic device, the solution having a solute comprising a species according to claim 1.

### Claim 29 (depends on 28)

A solution according to claim 28, further comprising a donor species.

### Claim 30 (depends on 28)

A method for forming a photovoltaic device, the method comprising applying the solution according to claim 28 to a substrate.

### Claim 31 (depends on 30)

A method according to claim 30, wherein the solution is applied to the substrate by inkjet printing or spin coating.

### Claim 32 (depends on 1)

A photovoltaic device comprising a charge transfer layer comprising a species according to claim 1.

### Claim 33 (depends on 32)

A photovoltaic device according to claim 32, wherein the charge transfer layer further comprises a donor species.

### Claim 34 (depends on 33)

A photovoltaic device according to claim 33, wherein the donor species comprises a donor polymer.

### Claim 35 (depends on 33)

A photovoltaic device according to claim 33, wherein the donor species comprises poly(3-hexylthiophene).

### Claim 36 (depends on 17)

A species according to claim 17, wherein the polymeric species is selected from the group consisting of a polymer, a dendrimer, and an oligomer.