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US 2011/0079773 A1Published application
Selectively Functionalized Rylene Imides and Diimides
OwnerMichael R. Wasielewski, Joseph E. Bullock +1inventors
InventorsMichael R. Wasielewski, Joseph E. Bullock, Michael T. Vagnini
Life of this patent
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Abstract
Disclosed are new selectively functionalized rylene imides and diimides that can exhibit desirable electronic properties and can possess processing advantages including solution-processability and/or good stability at ambient conditions.
Claims20
A compound of formula I:
- wherein:
- R1 and R2 independently are selected from H, a C1-40 alkyl group, a C2-40 alkenyl group, a C1-40 haloalkyl group, and an organic group comprising 1-4 cyclic moieties,
- wherein:
- each of the C1-40 alkyl group, the C2-40 alkenyl group, and the C1-40 haloalkyl group optionally is substituted with 1-10 substituents independently selected from a halogen, —CN, NO2, OH, —NH2, —NH(C1-40 alkyl), —N(C1-40 alkyl)2, —S(O)2OH, —CHO, —C(O)—C1-40 alkyl, —C(O)OH, —C(O)—OC1-40 alkyl, —C(O)NH2, —C(O)NH—C1-40 alkyl, —C(O)N(C1-40 alkyl)2, —OC1-40 alkyl, —SiH3, —SiH(C1-40 alkyl)2, —SiH2(C1-40 alkyl), and —Si(C1-40 alkyl)3;
- each of the C1-40 alkyl group, the C2-40 alkenyl group, the C1-40 haloalkyl group, and the organic group is bonded either directly or via an optional linker to the imide nitrogen;
- and
- each of the 1-4 cyclic moieties in the organic group is the same or different, is bonded either directly or via an optional linker to each other, and optionally is substituted with 1-5 substituents independently selected from a halogen, oxo, —CN, NO2, OH, ═C(CN)2, —NH2, —NH(C1-40 alkyl), —N(C1-40 alkyl)2, —S(O)2OH, —CHO, —C(O)OH, —C(O)—C1-40 alkyl, -sC(O)—OC1-40 alkyl, —C(O)NH2, —C(O)NH—C1-40 alkyl, —C(O)N(C1-40 alkyl)2, —SiH3, —SiH(C1-40 alkyl)2, —SiH2(C1-40 alkyl), —Si(C1-40 alkyl)3, —O—C1-40 alkyl, —O—C1-40 alkenyl, —O—C1-40 haloalkyl, a C1-40 alkyl group, a C1-40 alkenyl group, and a C1-40 haloalkyl group;
- and
- R3 is selected from SiR3, SiOR3, a C1-40 alkyl group, a C1-40 haloalkyl group, a C6-14 aryl group, a 5-14 membered heteroaryl group, a C3-14 cycloalkyl group, and a 3-14 membered cycloheteroalkyl group, wherein R, at each occurrence, independently is selected from a C1-40 alkyl group and a C1-40 haloalkyl group, and each of the C6-14 aryl group, the 5-14 membered heteroaryl group, the C3-14 cycloalkyl group, and the 3-14 membered cycloheteroalkyl group optionally is substituted with 1-10 substituents independently selected from a halogen, —CN, a C1-10 alkyl group, a C1-10 alkoxy group, and a C1-10 haloalkyl group;
- and
- n is 0, 1, or 2.
8 more elements
A compound of formula II:
- wherein:
- R7 and R8 independently are selected from H, halogen, —CN, a C1-10 alkyl group, a C1-10 alkoxy group, and a C1-10 haloalkyl group;
- or alternatively,
- R7 and R8 together can be:
- R10 is selected from SiR3, SiOR3, a C1-40 alkyl group, a C1-40 haloalkyl group, a C6-14 aryl group, a 5-14 membered heteroaryl group, a C3-14 cycloalkyl group, and a 3-14 membered cycloheteroalkyl group, wherein R, at each occurrence, independently is selected from a C1-40 alkyl group and a C1-40 haloalkyl group, and each of the C6-14 aryl group, the 5-14 membered heteroaryl group, the C3-14 cycloalkyl group, and the 3-14 membered cycloheteroalkyl group optionally can be substituted with 1-10 substituents independently selected from a halogen, —CN, a C1-10 alkyl group, a C1-10 alkoxy group, and a C1-10 haloalkyl group;
- R11 and R12 independently are selected from H, a C1-40 alkyl group, a C2-40 alkenyl group, a C1-40 haloalkyl group, and an organic group comprising 1-4 cyclic moieties,
- wherein:
- each of the C1-40 alkyl group, the C2-40 alkenyl group, and the C1-40 haloalkyl group optionally is substituted with 1-10 substituents independently selected from a halogen, —CN, NO2, OH, —NH2, —NH(C1-40 alkyl), —N(C1-40 alkyl)2, —S(O)2OH, —CHO, —C(O)—C1-40 alkyl, —C(O)OH, —C(O)—OC1-40 alkyl, —C(O)NH2, —C(O)NH—C1-40 alkyl, —C(O)N(C1-40 alkyl)2, —OC1-40 alkyl, —SiH3, —SiH(C1-40 alkyl)2, —SiH2(C1-40 alkyl), and —Si(C1-40 alkyl)3;
- each of the C1-40 alkyl group, the C2-40 alkenyl group, the C1-40 haloalkyl group, and the organic group is bonded either directly or via an optional linker to the imide nitrogen atom;
- and
- each of the 1-4 cyclic moieties in the organic group is the same or different, is bonded either directly or via an optional linker to each other, and optionally is substituted with 1-5 substituents independently selected from a halogen, oxo, —CN, NO2, OH, ═C(CN)2, —NH2, —NH(C1-40 alkyl), —N(C1-40 alkyl)2, —S(O)2OH, —CHO, —C(O)OH, —C(O)—C1-40 alkyl, —C(O)—OC1-40 alkyl, —C(O)NH2, —C(O)NH—C1-40 alkyl, —C(O)N(C1-40 alkyl)2, —SiH3, —SiH(C1-40 alkyl)2, —SiH2(C1-40 alkyl), —Si(C1-40 alkyl)3, —O—C1-40 alkyl, —O—C1-40 alkenyl, —O—C1-40 haloalkyl, a C1-40 alkyl group, a C1-40 alkenyl group, and a C1-40 haloalkyl group;
- R13 and R14 independently are selected from H, halogen, —CN, a C1-10 alkyl group, a C1-10 alkoxy group, and a C1-10 haloalkyl group;
- and
- m is 0, 1, 2, or 3.
11 more elements
Dependencies are inferred from the claim text.