Curable polymeric materials and related electronic devices
View Patent ↗Disclosed are curable linear polymers that can be used as active and/or passive organic materials in various electronic, optical, and optoelectronic devices. In some embodiments, the device can include an organic semiconductor layer and a dielectric layer prepared from such curable linear polymers. In some embodiments, the device can include a passivation layer prepared from the linear polymers described herein. The present linear polymers can be solution-processed, then cured thermally (particularly, at relatively low temperatures) and/or photochemically into various thin film materials with desirable properties.
1. An electronic device comprising a field-effect transistor having a semiconductor layer comprising a semiconducting electronic material, a dielectric layer comprising an insulating electronic material, and source, drain, and gate electrodes each comprising a conducting electronic material, wherein the field-effect transistor comprises:
an organic material comprising a linear polymer having a repeating unit of formula (A):
wherein:
X is selected from the group consisting of CH 2 , CHR, CR 2 , C(O), SiH 2 , SiHR, SiR 2 , NH, NR, O, and S;
Y is absent or selected from the group consisting of CH 2 , CHR, CR 2 , C(O), SiH 2 , SiHR, SiR 2 , NH, NR, O, and S;
Q 1 -Q 2 is CH═CH or
Q 3 -Q 4 is CR 1 ═CR 2 or
R is selected from the group consisting of a halogen, —OR 3 , —C(O)OR 3 , —OC(O)R 3 , —NR 4 R 5 , —C(O)NR 4 R 5 , —OC(O)NR 4 R 5 , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and an optionally substituted aryl or heteroaryl group;
R 1 and R 2 independently are selected from the group consisting of H, a halogen, —OR 3 , —C(O)OR 3 , —OC(O)R 3 , —NR 4 R 5 , —C(O)NR 4 R 5 , —OC(O)NR 4 R 5 , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and an optionally substituted aryl or heteroaryl group;
R 3 is a C 1-10 alkyl group or a —Si(C 1-10 alkyl) 3 group;
R 4 and R 5 independently are H or a C 1-10 alkyl group; and
m is 0, 1 or 2;
wherein either the dielectric layer comprises the organic material as the insulating electronic material or the organic material is in contact with at least one of the semiconducting electronic material, the insulating electronic material, and the conducting electronic material.
2. The electronic device of claim 1 , wherein the linear polymer comprises a repeating unit of formula (II):
wherein:
X is selected from the group consisting of CH 2 , CHR, CR 2 , C(O), and O;
Y is absent or selected from the group consisting of CH 2 , CHR, CR 2 , and C(O);
R is selected from the group consisting of a halogen, —OR 3 , —C(O)OR 3 , —OC(O)R 3 , —NR 4 R 5 , —C(O)NR 4 R 5 , —OC(O)NR 4 R 5 , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and an optionally substituted aryl or heteroaryl group, wherein R 3 is a C 1-10 alkyl group or a —Si(C 1-10 alkyl) 3 group, and R 4 and R 5 independently are H or a C 1-10 alkyl group;
R 1 and R 2 independently are selected from the group consisting of H, a halogen, —OR 3 , —C(O)OR 3 , —OC(O)R 3 , —NR 4 R 5 , —C(O)NR 4 R 5 , —OC(O)NR 4 R 5 , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and an optionally substituted aryl or heteroaryl group;
R 3 is a C 1-10 alkyl group or a —Si(C 1-10 alkyl) 3 group; and
R 4 and R 5 independently are H or a C 1-10 alkyl group.
3. The electronic device of claim 2 , wherein X and Y are CH 2 , and R 1 and R 2 are H.
4. The electronic device of claim 1 , wherein the linear polymer has a repeating unit of the formula:
5. The electronic device of claim 1 , wherein the linear polymer comprises a second repeating unit in addition to the repeating unit of formula (A), wherein the second repeating unit is selected to increase the dielectric constant of the linear polymer.
6. The electronic device of claim 1 , wherein the linear polymer is end-functionalized with a photocrosslinkable moiety selected from the group consisting of an acrylate group and a cinnamate group.
7. The electronic device of claim 1 , wherein the organic material comprising the linear polymer having a repeating unit of formula (A) is present in an organic layer coupled to the semiconductor layer, the gate electrode, or the source and drain electrodes, the organic layer functioning as a passivation layer or a surface-modifying layer.
8. The electronic device of claim 1 , wherein the organic material comprising the linear polymer having a repeating unit of formula (A) is present as an additive in the semiconductor layer.
9. The electronic device of claim 1 , wherein the field-effect transistor comprises a dielectric layer coupled to the semiconductor layer on one side and the gate electrode on another side, wherein the dielectric layer comprises the organic material comprising the linear polymer having a repeating unit of formula (A).
10. The electronic device of claim 9 , wherein the dielectric layer is in the form of a multi-layer laminate, and wherein at least one layer of the multi-layer laminate comprises the organic material comprising the linear polymer having a repeating unit of formula (A).
11. The electronic device of claim 10 , wherein the multi-layer laminate comprises at least one layer comprising a linear dielectric polymer that is different from the linear polymer having a repeating unit of formula (A).
12. The electronic device of claim 9 , wherein the dielectric layer comprises a crosslinked matrix of the linear polymer having a repeating unit of formula (A).
13. The electronic device of claim 9 , wherein the semiconductor layer comprises an organic semiconducting electronic material.
14. The electronic device of claim 9 , wherein the semiconductor layer comprises a metal oxide semiconducting electronic material.
15. The electronic device of claim 14 , wherein the metal oxide semiconducting electronic material comprises indium-gallium-zinc oxide.
16. The electronic device of claim 1 , wherein m is 0 or 1, Q 1 -Q 2 is CH═CH, Q 3 -Q 4 is CR 1 ═CR 2 , and R 1 and R 2 independently are selected from the group consisting of H, a halogen, —OR 3 , —C(O)OR 3 , —OC(O)R 3 , —NR 4 R 5 , —C(O)NR 4 R 5 , —OC(O)NR 4 R 5 , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and an optionally substituted aryl or heteroaryl group, wherein R 3 is a C 1-10 alkyl group or a —Si(C 1-10 alkyl) 3 group, and R 4 and R 5 independently are H or a C 1-10 alkyl group.
17. The electronic device of claim 2 , wherein X is selected from the group consisting of O, CH 2 , CHCF 3 , and C(O); Y is selected from the group consisting of CH 2 , C(O), CHOC(O)CH 3 , CHCH 3 , and CHCF 3 ; and R 1 and R 2 are H.
18. The electronic device of claim 2 , wherein X is O or CH 2 ; Y is absent; and R 1 and R 2 independently are selected from the group consisting of H, CF 3 , —C(O)OCH 3 , and a phenyl group.
19. The electronic device of claim 7 , wherein the passivation layer or the surface-modifying layer comprises a crosslinked matrix of the linear polymer having a repeating unit of formula (A).