Organic semiconducting compounds and related optoelectronic devices
AssigneeFlexterra, Inc.
InventorsAntonio Facchetti, Mark Seger, Ali Mohebbi
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Abstract
The present teachings relate to new organic semiconducting compounds and their use as active materials in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The present compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The present compounds can have good solubility in common solvents enabling device fabrication via solution processes.
Claims21
A polymer comprising a first repeating unit of the formula:
- wherein:
- pi-1 has a formula selected from the group consisting of:
- wherein:
- Y, at each occurrence, independently is selected from the group consisting of halogen, R1, and —(Ar1)p—R1;
- Ar1, at each occurrence, independently is an optionally substituted divalent C6-20 aryl or 5-20 membered heteroaryl group;
- R1, at each occurrence, independently is selected from the group consisting of H, —CN, —NO2, —OR, —SR, —C(O)OR, —C(O)R, —Si(R)3, and R;
- R8, at each occurrence, independently is H or R7;
- wherein R7 is selected from the group consisting of halogen, —CN, —NO2, —OR, —SR, —C(O)OR, —C(O)R, —Si(R)3, and R;
- wherein R is selected from the group consisting of a C1-40 alkyl group, a C1-40 haloalkyl group, a C2-40 alkenyl group, and a C2-40 alkynyl group;
- and
- p is 1, 2, 3 or 4;
- pi-2 is a covalent bond or an optionally substituted conjugated polycyclic moiety that is different from pi-1;
- and
- Sp1, Sp2, and Sp3 independently are a covalent bond or a conjugated spacer group comprising at least one of a conjugated linear linker and an optionally substituted conjugated monocyclic moiety.
A polymer comprising a first repeating unit of the formula:
- wherein:
- pi-1 has a formula selected from the group consisting of:
- wherein:
- Y, at each occurrence, independently is selected from the group consisting of halogen, R1, and —(Ar1)p—R1;
- Ar1, at each occurrence, independently is an optionally substituted divalent C6-20 aryl or 5-20 membered heteroaryl group;
- R1, at each occurrence, independently is selected from the group consisting of H, —CN, —NO2, —OR, —SR, —C(O)OR, —C(O)R, —Si(R)3, and R;
- wherein R is selected from the group consisting of a C1-40 alkyl group, a C1-40 haloalkyl group, a C2-40 alkenyl group, and a C2-40 alkynyl group;
- and
- p is 1, 2, 3 or 4;
- pi-2 is a covalent bond or an optionally substituted conjugated polycyclic moiety that is different from pi-1;
- and
- Sp1, Sp2, and Sp3 independently are a covalent bond or a conjugated spacer group comprising at least one of a conjugated linear linker and an optionally substituted conjugated monocyclic moiety;
- and
- wherein the polymer comprises a second repeating unit of the formula:
- wherein:
- pi-1′ has the formula:
- wherein:
- Y′, at each occurrence, independently is selected from the group consisting of halogen, R1′, and —(Ar1)p—R1′;
- Ar1′, at each occurrence, independently is an optionally substituted divalent C6-20 aryl or 5-20 membered heteroaryl group;
- R1′, at each occurrence, independently is selected from the group consisting of H, —C(O)OR4, —C(O)R4, —Si(R5)3, a C1-40 alkyl group, a C3-40 alkenyl group, a C3-40 alkynyl group, C1-40 haloalkyl group, a C1-40 alkoxy group, and a C1-40 thioalkyl group;
- wherein R4 is H or a C1-6 alkyl group;
- and R5 is a C1-6 alkyl group;
- and
- p′ is 1, 2, 3 or 4;
- pi-2′ is a covalent bond or an optionally substituted conjugated polycyclic moiety that is different from pi-1′;
- and
- each of Sp1′, Sp2′, and Sp3′ independently is a covalent bond or a conjugated spacer group having a formula selected from the group consisting of:
- wherein each Ar′ independently is an optionally substituted conjugated monocyclic moiety;
- Z′ is a conjugated linear linker;
- and m′ is 1, 2, 3 or 4;
- and
- provided the second repeating unit is different from the first repeating unit.
Dependencies are inferred from the claim text.