Phenanthro [1,10,9,8-c,d,e,f,g]carbazole polymers and their use as organic semiconductors
AssigneeMerck Patent GmbH
InventorsNicolas Blouin, William Mitchell, Changsheng Wang, Steven Tierney
Life of this patent
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Abstract
The invention relates to novel phenanthro[1,10,9,8-c,d,e,f,g]carbazole polymers, methods and materials for their preparation, their use as semiconductors in organic electronic (OE) devices, and to OE devices comprising these polymers.
Claims21
A conjugated polymer comprising one or more identical or different repeating units of formula I
- wherein
- R is on each occurrence identically or differently H, halogen, a 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—, —CR0═CR00— or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN, or R is an aryl, heteroaryl, aryloxy or heteroaryloxy group having 2 to 40 C atoms that is unsubstituted or substituted by one or more non-aromatic groups R1,
- R0 and R00 are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
- Ar is on each occurrence identically or differently an optionally substituted aryl or heteroaryl group, —CY1═CY2— or —C≡C—,
- Y1 and Y2 are independently of each other H, F, Cl or CN,
- 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 polymerisable group,
- Sp is a spacer group or a single bond,
- X0 is halogen,
- m is on each occurrence identically or differently 0, 1, 2 or 3,
- and wherein the benzene rings are optionally substituted with one or more groups R1.
A mixture or blend comprising one or more compounds or polymers selected from the group consisting of compounds and polymers having semiconducting, charge transport, hole/electron transport, hole/electron blocking, electrically conducting, photoconducting or light emitting properties and a conjugated polymer comprising one or more identical or different repeating units of formula I
- wherein
- R is on each occurrence identically or differently H, halogen, a 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—, —CR0═CR00— or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN, or R is an aryl, heteroaryl, aryloxy or heteroaryloxy group having 2 to 40 C atoms that is unsubstituted or substituted by one or more non-aromatic groups R1,
- R0 and R00 are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
- Ar is on each occurrence identically or differently an optionally substituted aryl or heteroaryl group, —CY1═CY2— or —C≡C—,
- Y1 and Y2 are independently of each other H, F, Cl or CN,
- 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 polymerisable group,
- Sp is a spacer group or a single bond,
- X0 is halogen,
- m is on each occurrence identically or differently 0, 1, 2 or 3,
- and wherein the benzene rings are optionally substituted with one or more groups R1.
An optical, electrooptical or electronic component or device, which is an OFET device or a bulk heterojunction OPV device, which comprises a conjugated polymer comprising one or more identical or different repeating units of formula I
- wherein
- R is on each occurrence identically or differently H, halogen, a 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—, —CR0═CR00— or —C≡C— and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN, or R is an aryl, heteroaryl, aryloxy or heteroaryloxy group having 2 to 40 C atoms that is unsubstituted or substituted by one or more non-aromatic groups R1,
- R0 and R00 are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
- Ar is on each occurrence identically or differently an optionally substituted aryl or heteroaryl group, —CY1═CY2— or —C≡C—,
- Y1 and Y2 are independently of each other H, F, Cl or CN,
- 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 polymerisable group,
- Sp is a spacer group or a single bond,
- X0 is halogen,
- m is on each occurrence identically or differently 0, 1, 2 or 3,
- and wherein the benzene rings are optionally substituted with one or more groups R1.
Dependencies are inferred from the claim text.