Photocurable polymeric dielectrics containing 6-substituted coumarin moieties and methods of preparation and use thereof

A thin film transistor device, comprising:

• a dielectric layer;
• a semiconductor layer;
• a gate electrode;
• a source electrode;
• and
• a drain electrode;
• wherein the dielectric layer is disposed between the semiconductor layer and the gate electrode;
• wherein the source electrode and the drain electrode are in contact with the semiconductor layer,
• wherein the dielectric layer comprises a polymeric film, the polymeric film comprising a polymer comprising a repeating unit having a pendant group comprising an optionally substituted coumarin-6-yl moiety, wherein the optionally substituted coumarin-6-yl moiety has a formula:
• wherein:
• R1 and R2 are independently selected from the group consisting of a) H, b) halogen, c) —CN, d) —NO2, e) —OR4, f) —N(R4)2, g) —CHO, h) —C(O)R4, i) —C(O)OR4, j) —C(O)N(R4)2, a C1-20 alkyl group, l) a C2-20 alkenyl group, m) a C2-20 alkynyl group, n) a C1-20 alkoxy group, o) a C1-20 alkylthio group, p) a C1-20 haloalkyl group, q) a —Y—C3-14 cycloalkyl group, r) a —Y—C6-14 aryl group, s) a —Y-3-14 membered cycloheteroalkyl group, and t) 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 C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 R5 groups;
• R3, at each occurrence, is independently selected from the group consisting of a) halogen, b) —CN, c) —NO2, d) —OR4, e) —N(R4)2, f) —CHO, g) —C(O)R4, h) —C(O)OR4, i) —C(O)N(R4)2, a C1-20 alkyl group, k) a C2-20 alkenyl group, l) a C2-20 alkynyl group, m) a C1-20 alkoxy group, n) a C1-20 alkylthio group, o) a C1-20 haloalkyl group, p) a —Y—C3-14 cycloalkyl group, q) a —Y—C6-14 aryl group, r) a —Y-3-14 membered cycloheteroalkyl group, and s) 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 C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 R5 groups,
• R4, at each occurrence, is independently selected from the group consisting of a) H, b) a C1-20 alkyl group, c) a C2-20 alkenyl group, d) a C2-20 alkynyl group, e) a C1-20 alkoxy group, f) a C1-20 alkylthio group, g) a C1-20 haloalkyl group, h) a —Y—C3-14 cycloalkyl group, i) a —Y—C6-14 aryl group, j) a —Y-3-14 membered cycloheteroalkyl group, and k) 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 C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-5 R5 groups;
• R5, at each occurrence, is independently selected from the group consisting of a) halogen, b) —CN, c) —NO2, d) —OH, e) —O—C6-14 aryl, f) —NH2, g) —NH—C1-10 alkyl, h) —N(C1-10 alkyl)2, i) —NH—C6-14 aryl, j) —N(C1-10 alkyl)-C6-14 aryl, k) —N(C6-14 aryl)2, l) —CHO, m) —C(O)—C1-10 alkyl, n) —C(O)—C6-14 aryl, o) —C(O)OH, p) —C(O)—OC1-10 alkyl, q) —C(O)—OC6-14 aryl, r) —C(O)NH2, s) —C(O)NH—C1-10 alkyl, t) —C(O)N(C1-10 alkyl)2, u) —C(O)NH—C6-14 aryl, v) —C(O)N(C1-10 alkyl)-C6-14 aryl, w) —C(O)N(C6-14 aryl)2, x) a C1-10 alkyl group, y) a C2-10 alkenyl group, z) a C2-10 alkynyl group, aa) a C1-10 alkoxy group, ab) a C1-10 alkylthio group, ac) a C1-10 haloalkyl group, ad) a —Y—C3-14 cycloalkyl group, ae) a —Y—C6-14 aryl group, af) a —Y-3-14 membered cycloheteroalkyl group, and ag) a —Y-5-14 membered heteroaryl group, wherein each of the C1-10 alkyl group, the C2-10 alkenyl group, the C2-10 alkynyl group, the C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 substituents independently selected from the group consisting of a halogen, CN, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a —O—C1-6 haloalkyl group, a —C(O)—C1-6 alkyl group, a —C(O)—C1-6 haloalkyl group, and a —C(O)—O—C1-6 alkyl group;
• Y, at each occurrence, is a divalent C1-6 alkyl group, a divalent C2-6 alkenyl group, a divalent C2-6 alkynyl group, or a covalent bond;
• and
• b is 0, 1, 2, or 3.