Organic semiconductors and devices incorporating same
View Patent ↗Disclosed are thionated fused-ring (aromatic) imides and diimides that can exhibit desirable electronic properties and can possess processing advantages including solution-processability and/or good stability at ambient conditions.
1. A compound having the formula:
wherein:
R 1 and R 2 independently are selected from H, a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, a C 1-40 haloalkyl group, and a C 3-40 cycloalkyl group, wherein the C 1-40 alkyl group and the C 1-40 haloalkyl group optionally can be substituted with 1-5 substituents independently selected from a —CN, NO 2 , —SO 3 H, —N(R 0 ) 3 + , —COR 0 , and —COOR 0 ; the C 2-40 alkenyl group and the C 2-40 alkynyl group optionally can be substituted with 1-5 substituents independently selected from a halogen, —CN, NO 2 , —SO 3 H, —N(R 0 ) 3 + , —COR 0 , and —COOR 0 ; and the C 3-40 cycloalkyl group optionally can be substituted with 1-5 substituents independently selected from a halogen, —CN, NO 2 , —SO 3 H, —N(R 0 ) 3 + , —COR 0 , —COOR 0 , a C 1-40 alkyl group and a C 1-40 haloalkyl group, wherein R 0 , at each occurrence, independently is H or a C 1-40 alkyl group;
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 , at each occurrence, independently is selected from H, F, Cl, Br, CN, NO 2 , and a C 1-6 haloalkyl group;
Z 1 , Z 2 , Z 3 , and Z 4 independently are selected from O, S, and Se, provided that at least one of Z 1 , Z 2 , Z 3 , and Z 4 is S or Se; and
m is 1.
2. The compound of claim 1 having a formula selected from:
wherein R 1 , R 2 , R 4 , R 5 , R 8 , and R 9 are as defined in claim 1 .
3. The compound of claim 2 , wherein:
each of R 4 , R 5 , R 8 , and R 9 is H;
two of R 4 , R 5 , R 8 , and R 9 are H, and the other two of R 4 , R 5 , R 8 , and R 9 are selected from F, Cl, Br, and CN; or
two of R 4 , R 5 , R 8 , and R 9 are CN, and the other two of R 4 , R 5 , R 8 , and R 9 are selected from F, Cl, and Br.
4. The compound of claim 1 having a formula selected from:
wherein R 1 , R 2 , R 4 , R 5 , and R 8 are as defined in claim 1 .
5. The compound of claim 1 having a formula selected from:
wherein R 1 and R 2 are as defined in claim 1 .
6. The compound of claim 1 having the formula:
wherein R 1 and R 2 are as defined in claim 1 .
7. The compound of claim 5 , wherein R 1 and R 2 are selected from a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, a C 1-40 haloalkyl group, and a C 3-8 -cycloalkyl group.
8. The compound of claim 7 , wherein R 1 and R 2 are selected from a linear C 1-40 alkyl group, a linear C 2-40 alkenyl group, a linear C 1-40 haloalkyl group, a branched C 3-40 alkyl group, a branched C 4-40 alkenyl group, and a branched C 3-40 haloalkyl group.
9. The compound of claim 1 having a formula selected from:
wherein R 1a , R 1b , R 2a and R 2b independently are a C 1-20 alkyl group or a C 1-20 haloalkyl group.
10. The compound of claim 9 , wherein R 1a and R 1b are different, and R 2a and R 2b are different.
11. The compound of claim 9 , wherein one of R 1a and R 1b is CH 3 , and one of R 2a and R 2b is CH 3 .
12. The compound of claim 9 , wherein one of R 1a and R 1b is —CH 2 CH 3 , and one of R 2a and R 2b is —CH 2 CH 3 .
13. A compound selected from:
14. A composition comprising one or more compounds of claim 1 dissolved or dispersed in a liquid medium.
15. A semiconductor material comprising one or more compounds of claim 1 .
16. A composite comprising a substrate and the semiconductor material of claim 15 deposited on the substrate.
17. An electronic, opto-electronic, or optical device comprising the semiconductor material of claim 15 .
18. The device of claim 17 , wherein the device is selected from an organic field-effect transistor, an organic light-emitting transistor, and an organic photovoltaic device.
19. An organic field-effect transistor or an organic light-emitting transistor comprising the semiconductor material of claim 15 and a dielectric material, wherein the dielectric material comprises an organic dielectric material, an inorganic dielectric material, or a hybrid organic/inorganic dielectric material.
20. An organic photovoltaic device comprising a p-type semiconductor material adjacent to the semiconductor material of claim 15 .