Polymerisable thieno[3,2-b]thiophenes
AssigneeMerck Patent GmbH
InventorsMartin Heeney, Weimin Zhang, Iain McCulloch
Life of this patent
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Abstract
The invention relates to novel polymerisable thieno[3,2-b]thiophenes, to their use as semiconductors or charge transport materials, in optical, electro-optical or electronic devices like 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 field effect transistors, light emitting devices or ID tags comprising the novel compounds.
Claims26
A compound of formula I
- R3-(A)a-(B)b-(C)c-(D)d-(E)e-R4
- wherein
- A, B, C, D and E are independently of each other a TT group of formula II
- or are selected from phenylene-1,4-diyl that is optionally substituted by one or two R1 groups that are different than H, thiophene-2,5-diyl that is optionally substituted by one or two R1 groups that are different than H, selenophene-2,5-diyl that is optionally substituted by one or two R1 groups that are different than H, and naphthalene-2,6-diyl that is optionally substituted by one or two R1 groups that are different than H,
- R1 and R2 independently of each other are each H, halogen, P-Sp-, P*-Sp, or straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which may be unsubstituted, mono- or polysubstituted by F, Cl, Br, I or CN, and wherein one or more non-adjacent CH2 groups are each independently optionally replaced by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —O—CO—O—, —S—CO—, —CO—S—, —CX1═CX2— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
- R3 and R4 are independently of each other P-Sp-, P*-Sp-, H, halogen, or straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which may be unsubstituted, mono- or polysubstituted by F, Cl, Br, I or CN, and wherein one or more non-adjacent CH2 groups are each independently optionally replaced by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —O—CO—O—, —S—CO—, —CO—S—, —CX1═CX2— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, with at least one of R3 and R4 being P-Sp- or P*Sp—,
- X1 and X2 are independently of each other H, F, Cl or CN,
- P is CH2═CH—COO—, CH2═C(CH3)—COO—, CH2═CH—, CH2═CH—O—, (CH2═CH)2CH—OCO—, (CH2═CH)2CH—O—,
- k1 is 0 or 1,
- P* is —OH or —O—Si—R0R00R000,
- Sp is a spacer group or a single bond,
- R0, R00 and R000 are independently of each other H, alkyl with 1 to 12 C-atoms or aryl, and
- a, b, c and d are independently of each other 0, 1, 2 or 3, with a+b+c+d >0;
- wherein the compound comprises two or three TT groups, or the compound comprises one, two or three TT groups and one, two, three or four groups selected from phenylene-1,4-diyl, thiophene-2,5-diyl, selenophene-2,5-diyl, and naphthalene-2,6-diyl which in each case is optionally substituted by one or two R1 groups that are different than H.
A compound of formula I
- R3-(A)a-(B)b-(C)c-(D)d-(E)e-R4 I
- wherein
- A, B, C, D and E are independently of each other a TT group of formula II
- or are selected from phenylene-1,4-diyl that is optionally substituted by one or two R1 groups that are different than H, thiophene-2,5-diyl that is optionally substituted by one or two R1 groups that are different than H, selenophene-2,5-diyl that is optionally substituted by one or two R1 groups that are different than H, and naphthalene-2,6-diyl that is optionally substituted by one or two R1 groups that are different than H,
- R1 and R2 independently of each other are each H, halogen, P-Sp-, P*-Sp, or straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which may be unsubstituted, mono- or polysubstituted by F, Cl, Br, I or CN, and wherein one or more non-adjacent CH2 groups are each independently optionally replaced by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —O—CO—O—, —S—CO—,—CO—S—, —CX1═CX2— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
- R3 and R4 are independently of each other P-Sp-, P*-Sp-, H, halogen, or straight chain, branched or cyclic alkyl with 1 to 20 C-atoms, which may be unsubstituted, mono- or polysubstituted by F, Cl, Br, I or CN, and wherein one or more non-adjacent CH2 groups are each independently optionally replaced by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —O—CO—O—, —S—CO—, —CO—S—, —CX1═CX2— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, with at least one of R3 and R4 being P-Sp- or P*-Sp-,
- X1 and X2 are independently of each other H, F, Cl or CN,
- P is CH2═CH—COO—, CH2═C(CH3)—COO—, CH2═CH—, CH2═CH—O—, (CH2═CH)2CH—OCO—, (CH2═CH)2CH—O—
- k1 is 0 or 1,
- P* is —OH or —O—Si—R0R00R000,
- Sp is a spacer group or a single bond,
- R0, R00 and R000 are independently of each other H, alkyl with 1 to 12 C-atoms or aryl, and
- a, b, c and d are independently of each other 0, 1, 2 or 3, with a+b+c+d >0;
- wherein the compound comprises two or three TT groups, or the compounds comprise one, two or three TT groups and one, two, three or four groups selected from phenylene-1,4-diyl, thiophene-2,5-diyl, selenophene-2,5-diyl, and naphthalene-2,6-diyl which in each case is optionally substituted by one or two R1 groups that are different than H, and
- wherein said compound is oxidatively or reductively doped to form a conducting ionic species.
Dependencies are inferred from the claim text.