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US 6,806,374 B2Granted
Mono-, oligo- and poly-3-(1,1-difluoroalkyl)thiophenes and their use as charge transport materials
AssigneeMerck Patent GmbH
InventorsMartin Heeney, Louise Farrand, Mark Giles, Marcus Thompson, Steven Tierney, Maxim Shkunov, David Sparrowe, Iain McCulloch
Life of this patent
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Abstract
Mono-, oligo- and polymers comprising one or more identical or different recurring units of formula I —[(Y)a—(D)b—(Z)c]— I wherein D is a 3-(1,1-difluoroalkyl)thiophene group of formula II, wherein Y, Z, R1, R2, a, b and c have the meanings defined herein, are useful as semiconductors and charge transport materials.
Claims51
A monmeric, oligomeric, or polymeric [3-(1,1-difluoroalkyl)thiophene] compound comprising one or more identical or different recurring units of formula I
- —[(Y)a—(D)b—(Z)c]— I
- wherein
- D is a 3-(1,1-difluoroalkyl)thiophene group of formula II
- R1 is H, straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which is unsubstituted, mono- or partially-substituted by F, Cl, Br, I, —CN or —OH, wherein optionally one or more non-adjacent CH2 groups is 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 optionally substituted heteroaryl,
- R2 is H, F, straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which is unsubstituted, mono- or poly-substituted by F, Cl, Br, I, —CN or —OH, wherein optionally one or more non-adjacent CH2 groups is replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —OCO—O—, —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 optionally substituted heteroaryl,
- R0 and R00 are independently of each other H or alkyl with 1 to 12 C-atoms,
- Y and Z are independently of each other —CX1═CX2—, —C≡C—, or optionally substituted arylene or heteroarylene,
- X1 and X2 are independently of each other H, F, Cl or CN, and
- a, b and c are independently of each other 0 or 1, with a+b+c>0, and wherein in at least one recurring unit b is 1,
- wherein if n and b both equal 1 and a and c both equal 0, then at least one of the terminal groups of the compound is not H.
7 more elements
Dependencies are inferred from the claim text.