Diimide-based semiconductor materials and methods of preparing and using the same

A compound having the formula:

• wherein:
• Q is a fused ring moiety optionally substituted with 1-4 Ra groups;
• wherein:
• Ra, at each occurrence, is independently a) a halogen, b) —CN, c) —NO2, d) oxo, e) —OH, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C1-20 alkylthio group, k) a C1-20 haloalkyl group, l) —Y-a C3-10 cycloalkyl group, m) —Y-a C6-14 aryl group, n) a —Y-3-12 membered cycloheteroalkyl group, or o) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4 Rb groups;
• Rb, at each occurrence, is independently a) a halogen, b) —CN, c) —NO2, d) oxo, e) —OH, f) —NH2, g) —NH(C1-20 alkyl), h) —N(C1-20 alkyl)2, i) —N(C1-20 alkyl)-Y—C6-14 aryl, j) —N(—Y—C6-14 aryl)2, k) —S(O)mH, l) —S(O)m—C1-20 alkyl, m) —S(O)2OH, n) —S(O)m—OC1-20 alkyl, o) —S(O)m—O—Y—C6-14 aryl, p) —CHO, q) —C(O) —C1-20 alkyl, r) —C(O)—Y—C6-14 aryl, s) —C(O)OH, t) —C(O) —OC1-20 alkyl, u) —C(O)—O—Y—C6-14 aryl, v) —C(O)NH2, w) —C(O)NH—C1-20 alkyl, x) —C(O)N(C1-20 alkyl)2, y) —C(O)NH—Y—C6-14 aryl, z) —C(O)N(C1-20 alkyl)-Y—C6-14 aryl, aa) —C(O)N(—Y—C6-14 aryl)2, ab) —C(S)NH2, ac) —C(S)NH—C1-20 alkyl, ad) —C(S)N(C1-20 alkyl)2, ae)-C(S)N(—Y—C6-14 aryl)2, af) —C(S)N(C1-20 alkyl)-Y—C6-14 aryl, ag) —C(S)NH—Y—C6-14 aryl, ah) —S(O)mNH2, ai) —S(O)mNH(C1-20 alkyl), aj) —S(O)mN(C1-20 alkyl)2, ak) —S(O)mNH(—Y—C6-14 aryl), al) —S(O)mN(C1-20 alkyl)-Y—C6-14 aryl, am) —S(O)mN(—Y—C6-14 aryl)2, an) —SiH3, ao) —SiH(C1-20 alkyl)2, ap) —SiH2(C1-20 alkyl), ar) —Si(C1-20 alkyl)3, as) a C1-20 alkyl group, at) a C2-20 alkenyl group, au) a C2-20 alkynyl group, av) a C1-20 alkoxy group, aw) a C1-20 alkylthio group, ax) a C1-20 haloalkyl group, ay) a —Y—C3-10 cycloalkyl group, az) a —Y—C6-14 aryl group, ba) a —Y-3-12 membered cycloheteroalkyl group, or bb) a —Y-5-14 membered heteroaryl group;
• Y, at each occurrence, is independently a divalent C1-6 alkyl group, a divalent C1-6 haloalkyl group, or a covalent bond;
• and
• m is 0, 1 or 2;
• and
• R1, at each occurrence, is independently a branched C3-20 alkyl group, a branched C3-20 alkenyl group, a branched C3-20 haloalkyl group, -L-Ar1—R2, or -L-Ar1—Ar1—R2;
• wherein:
• L, at each occurrence, is —Y—O—Y—, —Y—S—Y—, —Y—S(O)—Y—, —Y—C(O)—Y—, —Y—O—C(O)—Y—, —Y—NRcC(O)—Y—, —Y—C(O)NRc—Y—, —Y—NRc—Y—, —Y—[SiRC2]—Y—, a divalent C1-20 alkyl group, a divalent C1-20 haloalkyl group, or a covalent bond;
• wherein:
• Rc, at each occurrence, is H, a C1-6 alkyl group, or a —Y—C6-14 aryl group;
• Ar1, at each occurrence, is independently a C6-14 aryl group or a 5-14 membered heteroaryl group, each optionally substituted with 1-4 Rd groups;
• wherein:
• Rd, at each occurrence, is independently selected from a halogen, —CN, a C1-6 alkyl group, a C1-6 alkoxy group, and a C1-6 haloalkyl group;
• and
• R2, at each occurrence, is H, a halogen, a C1-20 alkyl group, a C2-20 alkenyl group, a C1-20 haloalkyl group, a C1-20 alkoxy group, -L′-Ar2—R3, or -L′-Ar2—Ar2—R3;
• wherein:
• L′, at each occurrence, is —Y—O—Y—, —Y—S—Y—, —Y—S(O)—Y—, —Y—C(O)—Y—, —Y—O—C(O)—Y—, —Y—NRcC(O)—Y—, —Y—C(O)NRc—Y—, —Y—NRc—Y—, —Y—[SiR2c]—Y—, a divalent C1-20 alkyl group, a divalent C1-20 haloalkyl group, or 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 1-4 Rd groups;
• and
• R3, at each occurrence, is H, a halogen, a C1-20 alkyl group, a C2-20 alkenyl group, a C1-20 haloalkyl group, or a C1-20 alkoxy group.