Silole-based polymers and semiconductor materials prepared from the same

A polymer comprising a repeating unit of Formula II:

• wherein:
• Z is S or CR8=CR9;
• R1 and R2 independently are a) H, b) a C1-20 alkyl group, c) a C2-20 alkenyl group, d) a C2-20 alkynyl group, e) a C1-20 haloalkyl group, f) a —Y—C3-14 cycloalkyl group, g) a —Y—C6-14 aryl group, h) a —Y-3-14 membered cycloheteroalkyl group, or i) 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 C1-20 haloalkyl group, the C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4-Y—R10 groups;
• R3, R4, R5, and R6 independently are a) H, b) halogen, c) —CN, d) —NO2, e) —OH, f) —NH2, g) —SH, h) —C(O)OH, i) —C(O)NH2, j) —S(O)2OH, k) —OC1-20 alkyl, l) —NH—C1-20 alkyl, m) —N(C1-20 alkyl)2, n) —C(O)—C1-20 alkyl, o) —C(O)—OC1-20 alkyl, p) —C(O)NH—C1-20 alkyl, q) —C(O)N(C1-20 alkyl)2, r) —S(O)m—C1-20 alkyl, s) —S(O)m—OC1-20 alkyl, t) —S(O)m—NHC1-20alkyl, u) —S(O)m—N(C1-20 alkyl)2, v) a C1-20 alkyl group, w) a C2-20 alkenyl group, x) a C2-20 alkynyl group, y) a C1-20 haloalkyl group, z) a C3-14 cycloalkyl group, aa) a C6-14 aryl group, ab) a 3-14 membered cycloheteroalkyl group, or ac) a 5-14 membered heteroaryl group;
• wherein each of the C1-20 alkyl groups, the C2-20 alkenyl group, the C2-20 alkynyl group, the C1-20 haloalkyl group, the C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4-Y—R10 groups;
• R8 and R9 independently are a) H, b) halogen, c) —CN, d) —NO2, e) —OH, f) —NH2, g) —SH, h) —C(O)OH, i) —C(O)NH2, j) —S(O)2OH, k) —OC1-20 alkyl, l) —NH—C1-20 alkyl, m) —N(C1-20 alkyl)2, n) —C(O)—C1-20 alkyl, o) —C(O)—OC1-20 alkyl, p) —C(O)NH—C1-20 alkyl, q) —C(O)N(C1-20 alkyl)2, r) —S(O)m—C1-20 alkyl, s) —S(O)m—OC1-20 alkyl, t) —S(O)m—NHC1-20 alkyl, u) —S(O)m—N(C1-20 alkyl)2, v) a C1-20 alkyl group, w) a C2-20 alkenyl group, x) a C2-20 alkynyl group, y) a C1-20 haloalkyl group, z) a C3-14 cycloalkyl group, aa) a C6-14 aryl group, ab) a 3-14 membered cycloheteroalkyl group, or ac) a 5-14 membered heteroaryl group, wherein each of the C1-20 alkyl groups, the C2-20 alkenyl group, the C2-20 alkynyl group, the C1-20 haloalkyl group, the C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-4-Y—R10 groups;
• R10, at each occurrence, independently is a) halogen, b) —NO2, c) —CN, d) oxo, e) —OH, f) —NH2, g) —SH, h) —C(O)OH, i) —C(O)NH2, j) —S(O)2OH, k) —OC1-20 alkyl, l) —NH—C1-20 alkyl, m) —N(C1-20 alkyl)2, n) —C(O)—C1-20 alkyl, o) —C(O)—OC1-20 alkyl, p) —C(O)NH—C1-20 alkyl, q) —C(O)N(C1-20 alkyl)2, r) —S(O)m—C1-20 alkyl, s) —S(O)m—OC1-20 alkyl, t) —S(O)m—NHC1-20 alkyl, u) —S(O)m—N(C1-20 alkyl)2, v) a C1-20 alkyl group, w) a C2-20 alkenyl group, x) a C2-20 alkynyl group, y) a C1-20 haloalkyl group, z) a C3-14 cycloalkyl group, aa) a C6-14 aryl group, ab) a 3-14 membered cycloheteroalkyl group, or ac) a 5-14 membered heteroaryl group;
• Y, at each occurrence, independently is a) a divalent C1-20 alkyl group, b) a divalent C2-20 alkenyl group, c) a divalent C2-20 alkynyl group, d) a divalent C1-20 haloalkyl group, or e) a covalent bond;
• m, at each occurrence, independently is 0, 1, or 2;
• and
• x is 2, 3, 4, 5, 6, 7, 8, 9, or 10.