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US 7,888,452 B2Granted
Low band gap semiconducting polymers
AssigneeNDSU Research Foundation
InventorsSeth C. Rasmussen, Jon P. Nietfeld
Life of this patent
Estimating the term…
Abstract
The invention provides a polymer of formula I: wherein A, B, D, E, R1, and R2 have any of the values defined in the specification, as well as electrical devices comprising such polymers.
Claims27
A polymer of formula (II):
- wherein:
- n is 2-100;
- A is a bond;
- and R1 is H, (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, (C1-C12)alkoxycarbonyl, cyano, halo, nitro, ReOSO2—, carboxy, trifluoromethyl, aryl, aryl(C1-C12)alkyl, —CH2CH2O(CH2CH2O)mCH3, or NRaRb;
- or A is O, S, or Se and R1 is H, (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C12)cycloalkyl, (C1-C12)alkanoyl, trifluoromethyl, aryl, or aryl(C1-C12)alkyl, or —CH2CH2O(CH2CH2O)mCH3;
- wherein each aryl is optionally substituted with one or more (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C1-C12)alkoxy, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, (C1-C12)alkanoyloxy, (C1-C12)alkoxycarbonyl, cyano, halo, nitro, carboxy, trifluoromethyl, trifluoromethoxy, or methylenedioxy;
- B is a bond;
- and R2 is H, (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, cyano, halo, nitro, ReOSO2—, carboxy, trifluoromethyl, aryl, aryl(C1-C12)alkyl, —CH2CH2O(CH2CH2O)mCH3, or NRcRd;
- or B is O, S, or Se and R2 is H, (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, trifluoromethyl, aryl, or aryl(C1-C12)alkyl, or —CH2CH2O(CH2CH2O)mCH3;
- wherein each aryl is optionally substituted with one or more (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C1-C12)alkoxy, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, (C1-C12)alkanoyloxy, (C1-C12)alkoxycarbonyl, cyano, halo, nitro, carboxy, trifluoromethyl, trifluoromethoxy, or methylenedioxy;
- Ra and Rb are each independently (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C1-C12)alkoxy, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, (C1-C12)alkanoyloxy, aryl, aryl(C1-C12)alkyl, —CH2CH2O(CH2CH2O)mCH3, or (C1-C12)alkoxycarbonyl;
- or Ra and Rb together with the nitrogen to which they are attached form a morpholino, thiomorpholino or pyrrolidino ring;
- Rc and Rd are each independently (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C1-C12)alkoxy, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, (C1-C12)alkanoyloxy, aryl, aryl(C1-C12)alkyl, —CH2CH2O(CH2CH2O)mCH3, or (C1-C12)alkoxycarbonyl;
- or Rc and Rd together with the nitrogen to which they are attached form a morpholino, thiomorpholino or pyrrolidino ring;
- Re is H or (C1-C12)alkyl;
- m is 0-5;
- D is absent or is phenyl, thienyl, bithienyl, terthienyl, quaterthienyl, or fluorenyl, which phenyl, thienyl, bithienyl, terthienyl, quaterthienyl, and fluorenyl is optionally substituted with one or more (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C1-C12)alkoxy, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, (C1-C12)alkanoyloxy, (C1-C12)alkoxycarbonyl, cyano, halo, nitro, carboxy, trifluoromethyl, trifluoromethoxy, or methylenedioxy;
- and
- E is absent or is phenyl, thienyl, bithienyl, terthienyl, quaterthienyl, or fluorenyl, which phenyl, thienyl, bithienyl, terthienyl, quaterthienyl, and fluorenyl is optionally substituted with one or more (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C1-C12)alkoxy, (C3-C8)cycloalkyl, (C1-C12)alkanoyl, (C1-C12)alkanoyloxy, (C1-C12)alkoxycarbonyl, cyano, halo, nitro, carboxy, trifluoromethyl, trifluoromethoxy, or methylenedioxy;
- or a salt thereof.
17 more elements
Dependencies are inferred from the claim text.