Conjugated copolymers of dithienothiophene with vinylene or acetylene
AssigneeMerck Patent GmbH
InventorsMark Giles, Louise Diane Farrand, Martin Heeney, Maxim Shkunov, David Sparrowe, Steven Tierney, Marcus Thompson, Iain McCulloch
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Abstract
Conjugated copolymers of dithienothiophene with vinylene or acetylene are suitable for use as semiconductors or charge transport materials in optical, electrooptical or electronic devices including field effect transistors, electroluminescent, photovoltaic and sensor devices.
Claims44
A conjugated copolymer comprising at least one dithienothiophene recurring unit and at least one vinylene or acetylene (ethinylene) recurring unit,
- wherein the dithienothiophene is substituted by one or two R1 groups and the vinylene group is unsubstituted or substituted by one or two X1 groups,
- R1 is halogen, optionally substituted aryl, optionally substituted heteroaryl, 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, and wherein one or more non-adjacent CH2 groups can be replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —CO—, —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, and
- X1 is F, Cl or CN.
A conjugated copolymer comprising at least one dithienothiophene recurring unit and at least one vinylene or acetylene (ethinylene) recurring unit,
- wherein the dithienothiophene is unsubstituted or substituted by one or two R1 groups and the vinylene group is substituted by one or two X1 groups,
- R1 is halogen, optionally substituted aryl, optionally substituted heteroaryl, 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, and wherein one or more non-adjacent CH2 groups can be 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, and
- X1 is F or Cl.
A polymer having identical or different recurring units selected of formula Ia
- wherein
- R1 and R2 are independently of each other H, halogen, optionally substituted aryl, optionally substituted heteroaryl, 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, and wherein one or more non-adjacent CH2 groups can be 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.
A copolymer according to clam 17, wherein optionally substituted aryl is a mono-, bi- or tricyclic aromatic group with up to 25 C atoms, wherein the rings can be fused, and which is unsubstituted or substituted with one or more of F, Cl, Br, I, CN, and straight chain, branched or cyclic alkyl having 1 to 20 C atoms, which is unsubstituted, mono- or poly-substituted by F, Cl, Br, I, —CN or —OH, and in which one or more non-adjacent CH2 groups are optionally 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, and
- optionally substituted heteroaryl is a mono-, bi- or tricyclic heteroaromatic group with up to 25 C atoms containing groups contain at least one hetero ring atom selected from N, O and S, wherein the rings can be fused, and which is unsubstituted or substituted with one or more of F, Cl, Br, I, CN, and straight chain, branched or cyclic alkyl having 1 to 20 C atoms, which is unsubstituted, mono- or poly-substituted by F, Cl, Br, I, —CN or —OH, and in which one or more non-adjacent CH2 groups are optionally 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.
A conjugated copolymer comprising at least one dithienothiophene recurring unit and at least one vinylene or acetylene (ethinylene) recurring unit, wherein said copolymer has identical or different recurring units selected of formula I
- wherein
- R1 and R2 are independently of each other H, halogen, optionally substituted aryl, optionally substituted heteroaryl, 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, and wherein one or more non-adjacent CH2 groups can be 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,
- R0 and R00 are independently of each other H or alkyl with 1 to 12 C-atoms,
- A is —CX1═CX2— or —C≡C—, and
- X1 and X2 are independently of each other H, F. Cl or CN.
A copolymer according to at least one of clam 21, having a degree of polymerisation from 10 to 5000.
Dependencies are inferred from the claim text.