Perylene-based semiconductors and methods of preparation and use thereof
View Patent ↗Provided are semiconductors prepared from an enantiomerically enriched mixture of a nitrogen-functionalized rylene bis(dicarboximide) compound. Specifically, the enantiomerically enriched mixture has unexpected electron-transport efficiency compared to the racemate or either of the enantiomers in optically pure form.
1. A thin film semiconductor comprising an enantiomerically enriched mixture of a compound of formula I:
wherein:
R 1 and R 2 are identical or substantially identical and are selected from the group consisting of a branched C 4-40 alkyl group, a branched C 4-40 alkenyl group, and a branched C 4-40 haloalkyl group; wherein the branched C 4-40 alkyl group, the branched C 4-40 alkenyl group, and the branched C 4-40 haloalkyl group have a formula selected from the group consisting of:
wherein R′ is a C 1-20 alkyl group or a C 1-20 haloalkyl group; R″ is different from R′ and is selected from the group consisting of a C 1-20 alkyl group, a C 2-20 alkenyl group, and a C 1-20 haloalkyl group; and an asterisk (*) denotes a stereogenic center such that R 1 and R 2 have either an R- or S-configuration; and
wherein a ratio of (R,R)-stereoisomers:(S,S)-stereoisomers or a ratio of (S,S)-stereoisomers:(R,R)-stereoisomers of the compound of formula I in the enantiomerically enriched mixture is between about 0.8:0.2 and about 0.98:0.02.
2. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein R′ is a C 1-6 alkyl group or a C 1-6 haloalkyl group; and R″ is different from R′ and is selected from the group consisting of a C 3-20 alkyl group, a C 3-20 alkenyl group, and a C 3-20 haloalkyl group; and a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
3. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein R′ is a C 1-6 alkyl group or a C 1-6 haloalkyl group; and R″ is different from R′ and is selected from the group consisting of a C 3-20 alkyl group, a C 3-20 alkenyl group, and a C 3-20 haloalkyl group; and a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
4. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein R′ is a C 1-6 alkyl group or a C 1-6 haloalkyl group; and R″ is different from R′ and is selected from the group consisting of a C 3-20 alkyl group, a C 3-20 alkenyl group, and a C 3-20 haloalkyl group; and a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
5. The thin film semiconductor of claim 2 , wherein R′ is selected from the group consisting of CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , and C 2 F 5 .
6. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
7. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
8. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
9. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
10. The thin film semiconductor of claim 1 , wherein the enantiomerically enriched mixture comprises two stereoisomers:
wherein a relative ratio of the two stereoisomers is between about 0.8:0.2 and about 0.98:0.02.
11. The thin film semiconductor of any one of claim 1 , wherein the ratio of (R,R)-stereoisomers:(S,S)-stereoisomers or the ratio of (S,S)- stereoisomers: (R,R)-stereoisomers is between about 0.90:0.10 and about 95:0.05.
12. A composite comprising a substrate and the thin film semiconductor of claim 1 deposited on the substrate.
13. An electronic device, an optical device, or an optoelectronic device comprising the thin film semiconductor of claim 1 .
14. An electronic device, an optical device, or an optoelectronic device comprising the composite of claim 12 .
15. A field effect transistor device comprising a source electrode, a drain electrode, a gate electrode, and the thin film semiconductor of claim 1 in contact with a dielectric material.
16. The field effect transistor device of claim 15 , wherein the field effect transistor has a structure selected from the group consisting of a top-gate bottom-contact structure, a bottom-gate top-contact structure, a top-gate top-contact structure, and a bottom-gate bottom-contact structure.
17. The field effect transistor device of claim 15 , wherein the dielectric material comprises an organic dielectric material, an inorganic dielectric material, or a hybrid organic/inorganic dielectric material.
18. The field effect transistor device of claim 15 , wherein the field effect transistor device exhibits a field effect mobility that is at least twice as high as an otherwise identical field effect transistor device comprising a thin film semiconductor comprising a 1:1 mixture of the (R,R)-stereoisomers and the (S,S)-stereoisomers of the compound of formula I.
19. The thin film semiconductor of claim 3 , wherein R′ is selected from the group consisting of CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , and C 2 F 5 .
20. The thin film semiconductor of claim 4 , wherein R′ is selected from the group consisting of CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , and C 2 F 5 .