Curable polymeric materials and their use for fabricating electronic devices
The present teachings relate to 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 transistor component 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 transistor component comprises:
an organic material comprising a linear polymer having a repeating unit of formula (A):
wherein:
X and Y independently are selected from the group consisting of CH 2 , CHR, CR 2 , C(O), SiH 2 , SiHR, SiR 2 , NH, NR, O, and S, wherein
R is selected from the group consisting of a halogen, —OR a , —C(O)OR a , —OC(O)R a , —NR b R c , —C(O)NR b R c , —OC(O)NR b R c , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and an optionally substituted aryl or heteroaryl group,
R a is a C 1-10 alkyl group or a —Si(C 1-10 alkyl) 3 group, and
R b and R c independently are H or a C 1-10 alkyl group;
W—Z is CH═CH or
R 1 , R 2 , R 3 , and R 4 independently are selected from the group consisting of H, —OR d , —C(O)OR d , —OC(O)OR d , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and L-Q, wherein
L is selected from the group consisting of —O—, —C(O), a divalent C 1-10 alkyl group, a divalent C 6-18 aryl group, a covalent bond, and combinations thereof,
Q is a crosslinkable group comprising, a —CH═CH 2 moiety, a —CH═CH—CH 3 moiety, a —CH═C(CH 3 ) 2 moiety, a —C(CH 3 )═CH 2 moiety, an ethynyl moiety, a dienyl moiety, an acrylate moiety, a coumarinyl moiety, an epoxy moiety, or a combination thereof, and
R d is H or a C 1-10 alkyl group,
provided that at least one of R 1 , R 2 , R 3 , and R 4 is L-Q; 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; and L-Q is selected from the group consisting of:
wherein R 1 is a H or C 1-20 alkyl group.
3. The electronic device of claim 2 , wherein X is CH 2 .
4. The electronic device of claim 1 , wherein the linear polymer having a repeat unit of formula (A) is derived from ring-opening metathesis polymerization of a monomer selected from the group consisting of:
wherein R′ is H or OCH 3 ; and n is an integer from 1 to 10.
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 represented by formula (C)
wherein:
X′ and Y′ independently are selected from the group consisting of CH 2 , CHR, CR 2 , C(O), SiH 2 , SiHR, SiR 2 , NH, NR, O, and S, wherein
R is selected from the group consisting of a halogen, —OR a , —C(O)OR a , —OC(O)R a , —NR b R c , —C(O)NR b R c , —OC(O)NR b R c , a C 1-10 alkyl group, a C 1-10 haloalkyl group, and an optionally substituted aryl or heteroaryl group,
R a is a C 1-10 alkyl group or a —Si(C 1-10 alkyl) 3 group, and
R b and R c independently are H or a C 1-10 alkyl group;
W′—Z′ is CH═CH or
R 6 , R 7 , R 8 , and R 9 independently are selected from the group consisting of H and -L-T, wherein
L′ is selected from the group consisting of —O—, —C(O)—, a divalent C 1-10 alkyl group, a divalent C 6-18 aryl group, a covalent bond, and combinations thereof; and
T is H, OH, a C 1-10 alkyl group, a C 1-10 haloalkyl group, a C 1-10 alkoxy group, an OC(O)(C 1-10 alkyl) group, a —Si(OC 1-10 alkyl) 3 group, and a phenyl group optionally substituted with 1-5 groups independently selected from halo, OH, a C 1-10 alkyl group, a C 1-10 haloalkyl group, and a C 1-10 alkoxy group; and
m′ is 0, 1 or 2.
6. 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 represented by
7. 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 represented by
wherein R 5 is selected from the group consisting of H, L′-T, and L′-Q, wherein
L is selected from the group consisting of —O—, —C(O)—, a divalent C 1-10 alkyl group, a divalent C 6-18 aryl group, a covalent bond, and combinations thereof;
L′ is selected from the group consisting of —O—, —C(O)—, a divalent C 1-10 alkyl group, a divalent C 6-18 aryl group, a covalent bond, and combinations thereof;
Q is a crosslinkable group comprising an ethenyl moiety, an ethynyl moiety, a dienyl moiety, an acrylate moiety, a coumarinyl moiety, an epoxy moiety, or a combination thereof; and
T is H, OH, a C 1-10 alkyl group, a C 1-10 haloalkyl group, a C 1-10 alkoxy group, an OC(O)(C 1-10 alkyl) group, a —Si(OC 1-10 alkyl) 3 group, and a phenyl group optionally substituted with 1-5 groups independently selected from halo, OH, a C 1-10 alkyl group, a C 1-10 haloalkyl group, and a C 1-10 alkoxy group.
8. The electronic device of claim 1 , wherein the linear polymer is partially hydrogenated.
9. The electronic device of claim 8 , wherein the linear polymer is partially hydrogenated such that no more than about 50% of the unsaturated bonds in the backbone of the linear polymer are hydrogenated.
10. 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.
11. The electronic device of claim 1 , wherein the organic material comprises a crosslinked matrix of the linear polymer.
12. 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.
13. The electronic device of claim 1 , wherein the organic material comprising the linear polymer having the repeating unit of formula (A) is present as an additive in the semiconductor layer.
14. 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).
15. The electronic device of claim 14 , 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).
16. The electronic device of claim 15 , 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).
17. The electronic device of claim 14 , wherein the dielectric layer comprises a crosslinked matrix of the linear polymer having a repeating unit of formula (A).
18. The electronic device of claim 14 , wherein the semiconductor layer comprises an organic semiconducting material.
19. The electronic device of claim 14 , wherein the semiconductor layer comprises a metal oxide semiconducting electronic material.
20. The electronic device of claim 19 , wherein the metal oxide semiconducting electronic material comprises indium-gallium-zinc oxide.
21. The electronic device of claim 1 , wherein Q is an epoxy moiety.
22. The electronic device of claim 1 , wherein X is CH 2 and m is 0.