Acene-based organic semiconductor materials and methods of preparing and using the same
View Patent ↗Acene-based compounds that can be used to prepare n-type semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including n-type semiconductor materials prepared from these compounds also are provided.
1. A field effect transistor device comprising a thin film semiconductor comprising a compound having the formula:
wherein:
R a is a straight chain C 1-10 alkyl group, a branched chain C 1-10 alkyl group, a straight chain C 1-10 haloalkyl group, a branched chain C 1-10 haloalkyl group, a straight chain C 2-10 alkenyl group, a branched chain C 2-10 alkenyl group, a C 3-10 cycloalkyl group, a C 6-14 aryl group, or a —C 1-6 alkyl-C 6-14 aryl group, wherein the C 6-14 aryl group is optionally substituted with 1-5 halogen groups;
R 9 and R 10 independently are CH or CR g ;
R g , at each occurrence, independently is Br, F, CN, or CF 3 ;
q and q′ independently are 0, 1, or 2; provided that the total number of R g groups is 1 to 6; and
wherein the field effect transistor device exhibits an on/off ratio of at least about 10 5 , and a field effect electron mobility greater than about 0.001 cm 2 /Vs.
2. The device of claim 1 , wherein R g is CN.
3. The device of claim 1 , wherein R 9 and R 10 are C(CN), and q and q′ are 0.
4. The device of claim 3 , wherein R a is a straight chain C 1-10 alkyl group or a branched chain C 1-10 alkyl group.
5. The device of claim 3 , wherein R a is a straight chain C 2-10 alkenyl group or a branched chain C 2-10 alkenyl group.
6. The device of claim 3 , wherein R a is a C 1-10 haloalkyl group or a phenyl group substituted with 1-5 halogen groups.
7. The device of claim 1 comprising a thin film semiconductor comprising a compound selected from:
8. A field effect transistor device comprising a thin film semiconductor comprising a compound having the formula:
wherein:
R a is a branched chain C 1-10 alkyl group, a branched chain C 1-10 haloalkyl group, or a branched chain C 2-10 alkenyl group;
R 9 and R 10 independently are CH or CR 9 ;
R 9 , at each occurrence, independently is Br, F, CN, or CF 3 ;
q and q′ independently are 0, 1, or 2; provided that the total number of R g groups is less than or equal to 6; and
wherein the field effect transistor device exhibits an on/off ratio of at least about 10 5 and a field effect electron mobility greater than about 0.001 cm 2 /Vs.
9. A field effect transistor device comprising a thin film semiconductor comprising a compound having the formula:
wherein:
R a is a C 3-10 cycloalkyl group, a C 6-14 aryl group, or a —C 1-6 alkyl-C 6-14 aryl group; wherein the C 6-14 aryl group is optionally substituted with 1-5 halogen groups;
R 9 and R 10 independently are CH or CR g ;
R g , at each occurrence, independently is Br, F, CN, or CF 3 ;
q and q′ independently are 0, 1, or 2; provided that the total number of R g groups is less than or equal to 6; and
wherein the field effect transistor device exhibits an on/off ratio of at least about 10 5 and a field effect electron mobility greater than about 0.001 cm 2 /Vs.
10. The device of claim 9 , wherein each R a is a perfluorophenyl group.