Polycyclic aromatic molecular semiconductors and related compositions and devices
View Patent ↗Disclosed are new semiconductor materials prepared from polycyclic aromatic compounds. Such compounds can exhibit high carrier mobility and/or good current modulation characteristics. In addition, the compounds of the present teachings can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.
1. A compound having formula IA or IB:
wherein:
W 1 and W 2 independently are —(CR a R b ) m ;
Z 1 and Z 2 independently are selected from the group consisting of O, S, and a covalent bond;
L, at each occurrence, independently is an electron-withdrawing group;
R a and R b , at each occurrence, independently are selected from the group consisting of H, a C 1-20 alkyl group, and a C 1-20 haloalkyl group;
R 1 , R 1′ , R 1″ , R 2 , R 2′ , and R 2″ independently are selected from the group consisting of H, a C 1-20 alkyl group, a C 2-20 alkenyl group, and a C 1-20 haloalkyl group, wherein at least two of R 1 , R 1′ , and R 1″ and at least two of R 2 , R 2′ , and R 2″ are selected from a C 1-20 alkyl group, a C 2-20 alkenyl group, and a C 1-20 haloalkyl group;
m, at each occurrence, independently is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and
n is 0, 1, 2, 3, 4, 5, 6, 7 or 8.
2. The compound of claim 1 , wherein the compound has formula IIA or IIB:
wherein L, R 1 , R 1′ , R 1″ , R 2 , R 2′ , R 2″ , Z 1 , Z 2 , m and n are as defined in claim 1 .
3. The compound of claim 1 , wherein the compound has formula IIIA or IIIB:
wherein L, R 1 , R 1′ , R 1″ , R 2 , R 2″ , R 2″ , m and n are as defined in claim 1 .
4. The compound of claim 1 , wherein the compound has formula VA or VB:
wherein L, R 1 , R 1′ , R 1″ , R 2 , R 2′ , R 2″ , m and n are as defined in claim 1 .
5. The compound of claim 1 , wherein each m independently is 1 or 2.
6. The compound of claim 5 , wherein R 1 , R 1′ , R 2 , and R 2′ independently are selected from the group consisting of a linear C 1-20 alkyl group, a linear C 2-20 alkenyl group, and a linear C 1-20 haloalkyl group; and R 1″ and R 2″ are H.
7. The compound of claim 6 , wherein L, at each occurrence, independently is selected from the group consisting of Br, CN, and NO 2 ; and n is 1, 2, 3, 4, 5, 6, 7 or 8.
8. The compound of claim 1 , wherein the compound has formula IIAa:
wherein R 1 and R 2 independently are selected from the group consisting of a linear C 3-20 alkyl group, a linear C 4-20 alkenyl group, and a linear C 3-20 haloalkyl group; R 1′ and R 2′ independently are selected from the group consisting of CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; and Z 1 , Z 2 , and m are as defined in claim 1 .
9. The compound of claim 8 , wherein the compound has formula IIAb or IIAc:
wherein R 1 , R 1′ , R 2 , R 2′ , Z 1 , Z 2 , and m are as defined in claim 8 .
10. The compound of claim 1 , wherein the compound has formula IIIAa or VAa:
wherein R 1 and R 2 independently are selected from the group consisting of a linear C 3-20 alkyl group, a linear C 4-20 alkenyl group, and a linear C 3-20 haloalkyl group; R 1′ and R 2′ independently are selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; and each m independently is selected from 0, 1, and 2.
11. The compound of claim 10 , wherein the compound has formula IIIAb, IIIAc, VAb, or VAc:
wherein R 1 , R 1′ , R 2 , R 2′ , and m are as defined in claim 10 .
12. A thin film semiconductor comprising a compound of claim 1 .
13. A composite comprising a substrate and the thin film semiconductor of claim 12 deposited on the substrate.
14. An electronic device, an optical device, or an optoelectronic device comprising the thin film semiconductor 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 12 in contact with a dielectric material, wherein the dielectric material comprises an organic dielectric material, an inorganic dielectric material, or a hybrid organic/inorganic dielectric material.
16. The field effect transistor device of claim 15 , wherein the field effect transistor has a structure selected from top-gate bottom-contact structure, bottom-gate top-contact structure, top-gate top-contact structure, and bottom-gate bottom-contact structure.
17. The compound of claim 1 , wherein the compound is
18. The compound of claim 1 , wherein the compound is
19. The compound of claim 1 , wherein the compound is
20. The compound of claim 1 , wherein the compound is