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US 8,709,290 B2Granted
Polymers derived from benzobis(silolothiophene) and their use as organic semiconductors
AssigneeMerck Patent GmbH
InventorsSteven Tierney, Clare Bailey, William Mitchell, Nicolas Blouin
Life of this patent
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Abstract
The invention relates to conjugated polymers comprising benzo-bis(silolothiophene) units or derivatives thereof, to methods of their preparation, to novel monomer units used therein, to the use of the polymers in organic electronic (OE) devices, and to OE devices comprising the polymers.
Claims19
Conjugated polymer comprising one or more identical or different repeating units of formula I
- wherein
- one of A1 and A2 is a single bond and the other is SiR1R2,
- one of A3 and A4 is a single bond and the other is SiR3R4,
- one of U1 and U2 is —CH═ or ═CH— and the other is —X—,
- one of U3 and U4 is —CH═ or ═CH— and the other is —X—,
- X is in each occurrence independently selected from —S— and —Se—,
- R1-4 are independently of each other identical or different groups selected from 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, P-Sp-, optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms,
- P is a polymerisable group,
- Sp is a spacer group or a single bond,
- X0 is halogen,
- R0 and R00 are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms,
- Ar1 and Ar2 are independently of each other 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,
- m1 and m2 are independently of each other 0 or 1, 2, 3 or 4.
11 more elements
Polymer comprising one or more identical or different repeating units selected from the following subformulae:
- wherein R1-4 are independently of each other identical or different groups selected from 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, P-Sp-, optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, n is an integer >1, and Ar an optionally substituted aryl or heteroaryl group, —CY1═CY2— or —C≡C
- P is a polymerisable group,
- Sp is a spacer group or a single bond,
- X0 is halogen,
- R0 and R00 are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms, and
- Y1 and Y2 are independently of each other H, F, Cl or CN.
3 more elements
A polymer formula Ib1:
- R5-(MU)n-R6 Ib1
- wherein R5 and R6 are R1, H, halogen, —CH2Cl, —CHO, —CH═CH2—SiR′R″R″′, —SnR′R″R″′, —BR′R″, —B(OR′)(OR″), —B(OH)2, or P-Sp, R′, R″ and R′″ are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms and R′ and R″ may also form a ring together with the hetero atom to which the are attached
- P is a polymerisable group,
- Sp is a spacer group or a single bond,
- X0 is halogen,
- and n is an integer >1, and “MU” is a monomeric repeating unit selected from subformulae I1-I32
- wherein R1-4 are independently of each other identical or different groups selected from 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, P-Sp-, optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, n is an integer >1 and Ar is a single bond, SiR1R2, or an optionally substituted aryl or heteroaryl group, —CY1═CY2— or —C≡C—
- P is a polymerisable group,
- Sp is a spacer group or a single bond,
- X0 is halogen,
- R0 and R00 are independently of each other H or an optionally substituted carbyl or hydrocarbyl group optionally comprising one or more hetero atoms, and
- Y1 and Y2 are independently of each other H, F, Cl or CN.
9 more elements
Dependencies are inferred from the claim text.