Organic Semiconducting Polymers

A homopolymer or copolymer comprising a repeating unit M1 selected from:

• wherein:
• R1, at each occurrence, is independently selected from H, a C1-40 alkyl group, a C2-40 alkenyl group, a C2-40 alkynyl group, a C1-40 haloalkyl group, -L-Ra, -L-Ar1,
• -L-Ar1—Ar1, -L-Ar1—Ra,-L-Ar1—Ar1—Ra, -L-Cy1, -L-Cy1-Cy1, -L-Cy1-Ra, and -L-Cy1-Cy1-Ra;
• wherein:
• L, at each occurrence, is independently selected from —O—, —Y—O—Y—, —S—,
• —S(O)—, —Y—S—Y—, —C(O)—, —NRcC(O)—, —C(O)NRc—, —SiRc2—,
• —Y—[SiRc2]—Y—, a divalent C1-20 alkyl group, a divalent C1-20 alkenyl group, a divalent C1-20 haloalkyl group, and a covalent bond;
• Ar1, at each occurrence, is independently a C6-14 aryl group or a 5-14 membered heteroaryl group, each optionally substituted with 1-5 substituents independently selected from a halogen, —CN, oxo, ═C(CN)2, a C1-6 alkyl group, a C1-6 alkoxy group, and a C1-6 haloalkyl group;
• Cy1, at each occurrence, is independently a C3-14 cycloalkyl group or a 3-14 membered cycloheteroalkyl group, each optionally substituted with 1-5 substituents independently selected from a halogen, —CN, oxo, ═C(CN)2, a C1-6 alkyl group, a C1-6 alkoxy group, and a C1-6 haloalkyl group;
• and
• Ra, at each occurrence, is independently selected from a C1-40 alkyl group, a C2-40 alkenyl group, a C2-40 alkynyl group, a C1-40 haloalkyl group, a C1-40 alkoxy group, -L′-Rb, -L′-Ar2, -L′-Ar2—Ar2, -L′-AR2—Rb, -L′-Ar2—Ar2—Rb, -L′-Cy2, -L′-Cy2-Cy2, -L′-Cy2-Rb, -L′-Cy2-Cy2-Rb;
• wherein:
• L′, at each occurrence, is independently selected from —O—, —Y—O—Y—, —S—, —S(O)—, —Y—S—Y—, —C(O)—, —NRcC(O)—, —C(O)NRc—, —SiRc2—, —Y—[SiRc2]—Y—, a divalent C1-20 alkyl group, a divalent C1-20 alkenyl group, a divalent C1-20 haloalkyl group, and a covalent bond;
• Ar2, at each occurrence, is independently a C6-14 aryl group or a 5-14 membered heteroaryl group, each optionally substituted with 1-5 substituents independently selected from halogen, —CN, oxo, ═C(CN)2, a C1-6 alkyl group, a C1-6 alkoxy group, and a C1-6 haloalkyl group;
• Cy2, at each occurrence, is independently a C3-14 cycloalkyl group or a 3-14 membered cycloheteroalkyl group, each optionally substituted with 1-5 substituents independently selected from a halogen, —CN, oxo, ═C(CN)2, a C1-6 alkyl group, a C1-6 alkoxy group, and a C1-6 haloalkyl group;
• Rb, at each occurrence, is independently selected from a C1-40 alkyl group, a C2-40 alkenyl group, a C2-40 alkynyl group, a C1-40 haloalkyl group, and a C1-40 group;
• Rc, at each occurrence, is independently selected from H, a C1-6 alkyl group, and a —Y—C6-14 aryl group;
• and
• Y, at each occurrence, is independently selected from a divalent C1-6 alkyl group, a divalent C1-6 haloalkyl group, and a covalent bond;
• Rd, at each occurrence, is a) halogen, b) —CN, c) —NO2, d) oxo, e) ═C(Re)2, f) a C1-40 alkyl group, g) a C2-40 alkenyl group, h) a C2-40 alkynyl group, i) a C1-40 haloalkyl group, j) a —Y—C3-10 cycloalkyl group, k) a —Y—C6-14 aryl group, l) a —Y—C6-14 haloaryl group, m) a —Y-3-12 membered cycloheteroalkyl group, or n) a —Y-5-14 membered heteroaryl group, wherein each of the C1-40 alkyl group, the C2-40 alkenyl group, the C2-40 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the C6-14 haloaryl group, the 3-12 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4 Re groups;
• wherein:
• Re, at each occurrence, is selected from a) halogen, b) —CN, c) —NO2, d) oxo, e) —OH, f) —O—C1-20 alkyl, g) —O—C6-14 aryl, h) —NH2, i) —NH(C1-20 alkyl), j) —N(C1-20 alkyl)2, k) —N(C1-20 alkyl)—C6-14 aryl, l) —N(C6-14 aryl)2, m) —S(O)mH, n) —S(O)m—C1-20 alkyl, o) —S(O)2OH, p) —S(O)m—OC1-20 alkyl, q) —S(O)m—OC6-14 aryl, r) —CHO, s) —C(O)—C1-20 alkyl, t) —C(O)—C6-14 aryl, u) —C(O)OH, v) —C(O)—OC1-20 alkyl, w) —C(O)—OC6-14 aryl, x) —C(O)NH2, y) —C(O)NH—C1-20 alkyl, z) —C(O)N(C1-20 alkyl)2, aa) —C(O)NH—C6-14 aryl, ab) —C(O)N(C1-20 alkyl)—C6-14 aryl, ac) —C(O)N(C6-14 aryl)2, ad) —C(S)NH2, ae) —C(S)NH—C1-20 alkyl, af) —C(S)N(C1-20 alkyl)2, ag) —C(S)N(C6-14 aryl)2, ah) —C(S)N(C1-20 alkyl)—C6-14 aryl, ai) —C(S)NH—C6-14 aryl, aj) —S(O)mNH2, ak) —S(O)mNH(C1-20 alkyl), al) —S(O)mN(C1-20 alkyl)2, am) —S(O)mNH(C6-14 aryl), an) —S(O)mN(C1-20 alkyl)—C6-14 aryl, ao) —S(O)mN(C6-14 aryl)2, ap) —SiH3, aq) —SiH(C1-20 alkyl)2, ar) —SiH2(C1-20 alkyl), as) —Si(C1-20 alkyl)3, at) a C1-20 alkyl group, au) a C2-20 alkenyl group, av) a C2-20 alkynyl group, aw) a C1-20 alkylthio group, ax) a C1-20 haloalkyl group, ay) a C3-10 cycloalkyl group, az) a C6-14 aryl group, ba) a C6-14 haloaryl group, bb) a 3-12 membered cycloheteroalkyl group, and bc) a 5-14 membered heteroaryl group;
• and
• q is 0, 1, 2 or3;
• wherein the homopolymer or copolymer has a degree of polymerization (n) that is greater than 2.