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US 9,287,504 B2Granted
Semiconducting polymers
AssigneeMerck Patent GmbH
InventorsNicolas Blouin, Steven Tierney, William Mitchell, Miguel Carrasco-Orozco, Frank Egon Meyer
Life of this patent
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Abstract
The invention relates to novel polymers containing repeating units based on benzodifuran, benzodipyrrole or benzodithiophene, monomers and methods for their preparation, their use as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers.
Claims16
A polymer comprising in said polymer identical or different repeating units of formula I
- wherein the asterisks indicate a link to neighboring groups, and the polymer is a conjugated polymer,
- X is O, S or NRx,
- R is, on each occurrence identically or differently, H, F, Cl, Br, I, CN, or straight-chain, branched or cyclic alkyl with 1 to 35 C atoms, in which one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —CR0═CR00— or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN, or denote aryl, heteroaryl, aryloxy, heteroaryloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy, heteroarylcarbonyloxy, aryloxycarbonyl or heteroaryloxycarbonyl having 4 to 30 ring atoms that is unsubstituted or substituted by one or more non-aromatic groups R1,
- Rx is on each occurrence identically or differently straight-chain, branched or cyclic alkyl with 1 to 30 C atoms, in which one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, O—CO—O—, —CR0═CR00— or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN,
- R0 and R00 are independently of each other H or optionally substituted carbyl or hydrocarbyl optionally comprising one or more hetero atoms,
- R1 is on each occurrence identically or differently H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(═O)NR0R00, —C(═O)X0, —C(═O)R0, —NH2, —NR0R00, —SH, —SR0, —SO3H, —SO2R0, —OH, —NO2, —CF3, —SF5, optionally substituted silyl, carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, or P-Sp-,
- P is a polymerizable or crosslinkable group,
- Sp is a spacer group or a single bond,
- X0 is halogen.
6 more elements
A monomer of formula Ia
- R2—U—R3 Ia
- wherein U is a unit of formula
- I
- wherein the asterisks indicate a link to neighboring groups,
- X is O, S or NRx,
- R is, on each occurrence identically or differently, H, F, Cl, Br, I, CN, or straight-chain, branched or cyclic alkyl with 1 to 35 C atoms, in which one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —CR0═CR00— or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN, or denote aryl, heteroaryl, aryloxy, heteroaryloxy, arylcarbonyl, heteroarylcarbonyl, arylcarbonyloxy, heteroarylcarbonyloxy, aryloxycarbonyl or heteroaryloxycarbonyl having 4 to 30 ring atoms that is unsubstituted or substituted by one or more non-aromatic groups R1,
- Rx is on each occurrence identically or differently straight-chain, branched or cyclic alkyl with 1 to 30 C atoms, in which one or more non-adjacent C atoms are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, O—CO—O—, —CR0═CR00— or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN,
- R0 and R00 are independently of each other H or optionally substituted carbyl or hydrocarbyl optionally comprising one or more hetero atoms,
- R1 is on each occurrence identically or differently H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(═O)NR0R00, —C(═O)X0, —C(═O)R0, —NH2, —NR0R00, —SH, —SR0, —SO3H, —SO2R0, —OH, —NO2, —CF3, —SF5, optionally substituted silyl, carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, or P-Sp-,
- P is a polymerizable or crosslinkable group,
- Sp is a spacer group or a single bond,
- X0 is halogen, and
- R2 and R3 are, independently of each other, Cl, Br, I, O-tosylate, O-triflate, O-mesylate, O-nonaflate, —SiMe2F, —SiMeF2, —O—SO2Z1, —B(OZ2)2, —CZ3═C(Z3)2, —C≡CH or —Sn(Z4)3, wherein Z1-4 are alkyl or aryl, each being optionally substituted, and two groups Z2 may also form a cyclic group.
10 more elements
Dependencies are inferred from the claim text.