Granted Patent B2

US 8,937,301 · App. 13/128,961 · Granted Jan 20, 2015

Abstract

Claims (64)

1. 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:

R 1 and R 2 are independently selected from the group consisting of a) H, b) halogen, c) —CN, d) —NO 2 , e) —OR 4 , f) —N(R 4 ) 2 , g) —CHO, h) —C(O)R 4 , i) —C(O)OR 4 , j) —C(O)N(R 4 ) 2 , a C 1-20 alkyl group, l) a C 2-20 alkenyl group, m) a C 2-20 alkynyl group, n) a C 1-20 alkoxy group, o) a C 1-20 alkylthio group, p) a C 1-20 haloalkyl group, q) a —Y—C 3-14 cycloalkyl group, r) a —Y—C 6-14 aryl group, s) a —Y-3-14 membered cycloheteroalkyl group, and t) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 R 5 groups;

R 3 , at each occurrence, is independently selected from the group consisting of a) halogen, b) —CN, c) —NO 2 , d) —OR 4 , e) —N(R 4 ) 2 , f) —CHO, g) —C(O)R 4 , h) —C(O)OR 4 , i) —C(O)N(R 4 ) 2 , a C 1-20 alkyl group, k) a C 2-20 alkenyl group, l) a C 2-20 alkynyl group, m) a C 1-20 alkoxy group, n) a C 1-20 alkylthio group, o) a C 1-20 haloalkyl group, p) a —Y—C 3-14 cycloalkyl group, q) a —Y—C 6-14 aryl group, r) a —Y-3-14 membered cycloheteroalkyl group, and s) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 R 5 groups,

R 4 , at each occurrence, is independently selected from the group consisting of a) H, b) a C 1-20 alkyl group, c) a C 2-20 alkenyl group, d) a C 2-20 alkynyl group, e) a C 1-20 alkoxy group, f) a C 1-20 alkylthio group, g) a C 1-20 haloalkyl group, h) a —Y—C 3-14 cycloalkyl group, i) a —Y—C 6-14 aryl group, j) a —Y-3-14 membered cycloheteroalkyl group, and k) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-5 R 5 groups;

R 5 , at each occurrence, is independently selected from the group consisting of a) halogen, b) —CN, c) —NO 2 , d) —OH, e) —O—C 6-14 aryl, f) —NH 2 , g) —NH—C 1-10 alkyl, h) —N(C 1-10 alkyl) 2 , i) —NH—C 6-14 aryl, j) —N(C 1-10 alkyl)-C 6-14 aryl, k) —N(C 6-14 aryl) 2 , l) —CHO, m) —C(O)—C 1-10 alkyl, n) —C(O)—C 6-14 aryl, o) —C(O)OH, p) —C(O)—OC 1-10 alkyl, q) —C(O)—OC 6-14 aryl, r) —C(O)NH 2 , s) —C(O)NH—C 1-10 alkyl, t) —C(O)N(C 1-10 alkyl) 2 , u) —C(O)NH—C 6-14 aryl, v) —C(O)N(C 1-10 alkyl)-C 6-14 aryl, w) —C(O)N(C 6-14 aryl) 2 , x) a C 1-10 alkyl group, y) a C 2-10 alkenyl group, z) a C 2-10 alkynyl group, aa) a C 1-10 alkoxy group, ab) a C 1-10 alkylthio group, ac) a C 1-10 haloalkyl group, ad) a —Y—C 3-14 cycloalkyl group, ae) a —Y—C 6-14 aryl group, af) a —Y-3-14 membered cycloheteroalkyl group, and ag) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-10 alkyl group, the C 2-10 alkenyl group, the C 2-10 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 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 C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a —O—C 1-6 haloalkyl group, a —C(O)—C 1-6 alkyl group, a —C(O)—C 1-6 haloalkyl group, and a —C(O)—O—C 1-6 alkyl group;

Y, at each occurrence, is a divalent C 1-6 alkyl group, a divalent C 2-6 alkenyl group, a divalent C 2-6 alkynyl group, or a covalent bond; and

b is 0, 1, 2, or 3.

2. The device of claim 1 , wherein R 1 and R 2 independently are selected from the group consisting of H, F, —CN, and CF 3 .

3. The device of claim 1 , wherein R 3 , at each occurrence, is independently selected from the group consisting of a halogen, OH, —CN, a C 1-6 alkyl group, a C 1-6 haloalkyl group, and a C 1-6 alkoxyl group.

4. The device of claim 1 , wherein the polymer comprises at least one repeating unit of a formula selected from the group consisting of:

wherein:

Q is -(L″)-L′″-; and

R 6 , R 7 , and R 8 are independently selected from the group consisting of H, a halogen, a C 1-10 alkyl group, and a C 6-14 aryl group, wherein each of the C 1-10 alkyl group and the C 6-14 aryl group is optionally substituted with 1-5 R 5 groups;

L″, at each occurrence, is independently selected from the group consisting of —Y″—, —(Y″) m —O—, —Y″—NR 4 —, —Y″—C(NR 4 )—, —Y″—Si(R 4 ) 2 —, —O—Si(R 4 ) 2 —, and a covalent bond;

L″′ is linked to the coumarin moiety and is selected from the group consisting of —C(O)—, —C(O)—O—, —O—C(O)—, —C(O)—Y″′—O—, —O—Y″—C(O)—, —C(O)—NR 4 —, —NR 4 —C(O)—, —C(O)—Y″′—NR 4 —, —NR 4 —Y″′—C(O)— —O—S(O) k —, —O—Y″′—S(O) k —, and a covalent bond;

Y″, at each occurrence, is selected from the group consisting of a divalent C 1-6 alkyl group, a divalent C 2-6 alkenyl group, and a divalent C 6-14 aryl group, wherein each of the C 1-6 alkyl group, the C 2-6 alkenyl group, and the C 6-14 aryl group is optionally substituted with 1-5 R 5 groups;

Y″′ is selected from the group consisting of a divalent C 1-6 alkyl group, a divalent C 2-6 alkenyl group, and a divalent C 6-14 aryl group, wherein each of the C 1-6 alkyl group, the C 2-6 alkenyl group, and the C 6-14 aryl group is optionally substituted with 1-5 R 5 groups;

k is 0, 1, or 2;

m is 1, 2, 3, 4, 5, or 6;

p is an integer in a range from 0 to 10;

R 1 and R 2 are independently selected from the group consisting of a) H, b) halogen, c) —CN, d) —NO 2 , e) —OR 4 , f) —N(R 4 ) 2 , g) —CHO, h) —C(O)R 4 , i) —C(O)OR 4 , j) —C(O)N(R 4 ) 2 , a C 1-20 alkyl group, l) a C 2-20 alkenyl group, m) a C 2-20 alkynyl group, n) a C 1-20 alkoxy group, o) a C 1-20 alkylthio group, p) a C 1-20 haloalkyl group, q) a —Y—C 3-14 cycloalkyl group, r) a —Y—C 6-14 aryl group, s) a —Y-3-14 membered cycloheteroalkyl group, and t) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 R 5 groups;

R 3 , at each occurrence, is independently selected from the group consisting of a) halogen, b) —CN, c) —NO 2 , d) —OR 4 , e) —N(R 4 ) 2 , f) —CHO, g) —C(O)R 4 , h) —C(O)OR 4 , i) —C(O)N(R 4 ) 2 , a C 1-20 alkyl group, k) a C 2-20 alkenyl group, l) a C 2-20 alkynyl group, m) a C 1-20 alkoxy group, n) a C 1-20 alkylthio group, o) a C 1-20 haloalkyl group, p) a —Y—C 3-14 cycloalkyl group, q) a —Y—C 6-14 aryl group, r) a —Y-3-14 membered cycloheteroalkyl group, and s) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 R 5 groups,

R 4 , at each occurrence, is independently selected from the group consisting of a) H, b) a C 1-20 alkyl group, c) a C 2-20 alkenyl group, d) a C 2-20 alkynyl group, e) a C 1-20 alkoxy group, f) a C 1-20 alkylthio group, g) a C 1-20 haloalkyl group, h) a —Y—C 3-14 cycloalkyl group, i) a —Y—C 6-14 aryl group, j) a —Y-3-14 membered cycloheteroalkyl group, and k) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-5 R 5 groups;

R 5 , at each occurrence, is independently selected from the group consisting of a) halogen, b) —CN, c) —NO 2 , d) —OH, e) —O—C 6-14 aryl, f) —NH 2 , g) —NH—C 1-10 alkyl, h) —N(C 1-10 alkyl) 2 , i) —NH—C 6-14 aryl, j) —N(C 1-10 alkyl)-C 6-14 aryl, k) —N(C 6-14 aryl) 2 , l)—CHO, m) —C(O)—C 1-10 -alkyl, n) —C(O)—C 6-14 aryl, o) —C(O)OH, p) —C(O)—OC 1-10 alkyl, q) —C(O)—OC 6-14 aryl, r) —C(O)NH 2 , s) —C(O)NH—C 1-10 alkyl, t) —C(O)N(C 1-10 alkyl) 2 , u) —C(O)NH—C 6-14 aryl, v) —C(O)N(C 1-10 alkyl)-C 6-14 aryl, w) —C(O)N(C 6-14 aryl) 2 , x) a C 1-10 alkyl group, y) a C 2-10 alkenyl group, z) a C 2-10 alkynyl group, aa) a C 1-10 alkoxy group, ab) a C 1-10 alkylthio group, ac) a C 1-10 haloalkyl group, ad) a —Y—C 3-14 cycloalkyl group, ae) a —Y—C 6-14 aryl group, af) a —Y-3-14 membered cycloheteroalkyl group, and ag) a —Y-5-14 membered heteroaryl group, wherein each of the C 1-10 alkyl group, the C 2-10 alkenyl group, the C 2-10 alkynyl group, the C 3-14 cycloalkyl group, the C 6-14 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 C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a —O—C 1-6 haloalkyl group, a —C(O)—C 1-6 alkyl group, a —C(O)—C 1-6 haloalkyl group, and a —C(O)—O—C 1-6 alkyl group; and

b is 0, 1, 2, or 3.

5. The device of claim 1 , wherein the polymer comprises at least one repeating unit of a formula selected from the group consisting of:

6. The device of claim 1 , configured as a top-gate device structure and comprising an interlayer between the dielectric layer and the semiconductor layer.

7. 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, and

wherein the polymer is selected from the group consisting of a vinyl polymer, a siloxane polymer, polymaleimide, polyethylene amine, and at least one copolymer thereof, and comprises a repeating unit having a pendant group comprising an optionally substituted coumarin-6-yl moiety.

8. The device of claim 7 , wherein the polymer is a vinyl polymer selected from the group consisting of polystyrene, polyvinyl phenol, polyvinyl alcohol, polyvinyl acetate, polymethyl methacrylate, and at least one copolymer thereof, and comprises a repeating unit having a pendant group comprising an optionally substituted coumarin-6-yl moiety.

9. The device of claim 7 , configured as a top-gate device structure and comprising an interlayer between the dielectric layer and the semiconductor layer.

10. 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, and

wherein the polymer has at least one selected from the group consisting of:

a dielectric constant between about 1.1 and about 5.0;

a glass transition temperature (T g ) between about 100° C. and about 200° C.;

a solubility of greater than about 0.1 mg/mL in a solvent selected from the group consisting of anisole, xylene, cyclopentanone, cyclohexane and cyclohexanone;

a maximum absorbance wavelength in the range of about 250 nm and about 500 nm; and

a molecular weight between about 10,000 Da and about 100,000 Da.

11. The device of claim 10 , configured as a top-gate device structure and comprising an interlayer between the dielectric layer and the semiconductor layer.

Assignments (9)