Poly(benzodithiophenes)
AssigneeMerck Patent GmbH
InventorsMartin Heeney, Clare Bailey, Steven Tierney, Weimin Zhang, Iain McCulloch
Life of this patent
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Abstract
Disclosed are novel poly(benzodithiophenes), their use as semiconductors or charge transport materials in optical, electro-optical or electronic devices, for example, liquid crystal displays, optical films, organic field effect transistors (FET or OFET) for thin film transistor liquid crystal displays and integrated circuit devices such as RFID tags, electroluminescent devices in flat panel displays, and in photovoltaic and sensor devices, and to a field effect transistor, light emitting device or ID tag.
Claims24
An oligo- or polymer comprising in its backbone 3 to 5000 identical or different recurring benzodithiophene-2,6-diyl groups, which are, each independently, substituted in 3- and 7- position and/or in 4- and 8-position, with the proviso that oligo- and poly(4,8-bisalkoxybenzodithiophenes) are excluded.
An oligo- or polymer, comprising in its backbone 3 to 5000 identical or different recurring units of formula I
- wherein
- R1 to R4 are, independently of each other, H, halogen or straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which is unsubstituted, mono- or poly-substituted by F, Cl, Br, I or CN, in which optionally one or more non-adjacent CH2 groups are replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CH═CH— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, or optionally substituted aryl or heteroaryl, or P-Sp-,
- P is a polymerizable or reactive group,
- Sp is a spacer group or a single bond,
- R0 and R00 are, independently of each other, H or alkyl with 1 to 12 C-atoms,
- Ar1 and Ar2 are, independently of each other, —CX1═CX2—, —C≡C—, an arylene or heteroarylene group that is optionally substituted with one or more groups R1 , or a single bond,
- X1 and X2 are, independently of each other, H, F, Cl or CN,
- with the provisos that
- a) in at least one recurring unit R1 to R2 are different from H and/or R3 and R4 are different from H, and
- b) R1 to R2 do not at the same time denote alkoxy groups.
An oligo- or polymer, comprising in its backbone a unit of formula I1
- wherein
- n is 3 to 5000, whereby 3 to 5000 recurring units of the structure in the brackets are present in a unit of formula I1 in the backbone of the oligo- or polymer, and wherein said 3 to 5000 recurring units may be identical or different,
- R1 to R4 are, independently of each other, H, haloaen or straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which is unsubstituted, mono- or poly-substituted by F, Cl, Br, I or CN, in which optionally one or more non-adjacent CH2 groups are replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CH═CH— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, or optionally substituted aryl or heteroaryt, or P-Sp-,
- P is a polymerizable or reactive group,
- Sp is a spacer group or a single bond,
- R0 and R00 are, independently of each other, H or alkyl with 1 to 12 C-atoms,
- Ar1 and Ar2 are, independently of each other, —CX1═CX2—, —C≡C—, an arylene or heteroarylene group that is optionally substituted with one or more groups R1 , or a single bond,
- X1 and X2 are, independently of each other, H, F, Cl or CN,
- with the provisos that
- a) in at least one recurring unit R1 to R2 are different from H and/or R3 and R4 are different from H, and
- b) R1 to R2 do not at the same time denote alkoxy groups.
An oligo- or polymer of formula I1a
- wherein
- n is 3 to 5000, whereby 3 to 5000 recurring units of the structure in the brackets are present in the oligo- or polymer of formula I1a, and wherein said 3 to 5000 recurring units may be identical or different,
- R5 and R6 are, independently of each other, H, halogen, —Sn(R0)3, —B(OR′)(OR″), —CH2Cl, —CHO, —CH═CH2, —SiR0R00R000, optionally substituted aryl or heteroaryl or P-Sp-, or alkyl with 1 to 12 C-atoms,
- R0, R00 and R000 are, independently of each other, H or alkyl with 1 to 12 C-atoms,
- R′ and R″ are, independently of each other, H or alkyl with 1 to 12 C-atoms, or
- OR′ and OR″ together with the boron atom form a cyclic group having 2 to 20 C atoms,
- P is a polymerizable or reactive group,
- Sp is a spacer group or a single bond,
- R1 to R4 are, independently of each other, H, halogen or straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which is unsubstituted, mono- or poly-substituted substituted by F, Cl, Br, I or CN, in which optionally one or more non-adjacent CH2 groups are replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CH═CH— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, or optionally substituted aryl or heteroaryl, or P-Sp-,
- Ar1 and Ar2 are, independently of each other, —CX1═CX2—, —C≡C—, an arylene or heteroarylene group that is optionally substituted with one or more groups R1 , or a single bond, and
- X1 and X2 are, independently of each other, H, F, Cl or CN,
- with the provisos that
- a) in at least one recurring unit R1 to R2 are different from H and/or R3 and R4 are different from H, and
- b) R1 to R2 do not at the same time denote alkoxy groups.
Dependencies are inferred from the claim text.