Organic semiconductor materials and methods of preparing and use thereof
View Patent ↗Solution-processable organic n-type semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including the organic n-type semiconductor materials also are provided.
1. A dimeric compound having the formula:
wherein:
L is a divalent C 1-20 alkyl group; and
Q and Q′ have the formula:
wherein:
Z is NR b , wherein R b is a C 1-20 alkyl group, a C 1-20 haloalkyl group, a C 2-20 alkenyl group, a C 3-10 cycloalkyl group, or a —Y—C 6-14 aryl group optionally substituted with 1-4 groups independently selected from a halogen, a C 1-20 alkyl group, and a C 1-20 alkoxy group, wherein Y is a divalent C 1-20 alkyl group;
each of a and b is CR m , wherein R m is —CN, —OR i , a halogen, a C 1-20 haloalkyl group, or a 3-12 membered cycloheteroalkyl group, wherein R i is a C 1-20 alkyl group or a phenyl group optionally substituted with 1-4 C 1-20 alkyl groups; and
each of c, d, e, f, g and h is CH.
2. The dimeric compound of claim 1 , wherein the dimeric compound has the formula:
wherein Q and Q′ are as defined in claim 1 .
3. The dimeric compound of claim 1 , wherein R m is Br, Cl, —CN, CF 3 , N-pyrrolidine, or a 3,5-di-tert-butylphenoxy group.
4. The dimeric compound of claim 1 , wherein Q and Q′ have the formula:
wherein Z is as defined in claim 1 .
5. The dimeric compound of claim 1 , wherein Z is NR b and R b is a straight chain C 1-20 alkyl group, a branched C 3-20 alkyl group, a branched C 4-20 alkenyl group, a C 1-20 fluoroalkyl group, or a C 3-10 cycloalkyl group.
6. The dimeric compound of claim 1 , wherein Z is NR b and R b is —C 8 H 17 , —C 12 H 25 , —CH(C 6 H 13 ) 2 , —CH(C 11 H 23 ) 2 , —CH 2 C 3 F 7 , or —CH 2 C 7 F 15 .
7. The dimeric compound of claim 1 , wherein Z is NR b and R b is a cyclohexyl group, a benzyl group, a 4-butyl benzyl group, a 2,3,4,5,6-pentafluorophenyl group, or a 3,4,5-tris(dodecyloxy)phenyl group.
8. A composition comprising the dimeric compound of claim 1 dissolved in an organic solvent.
9. A thin film semiconductor comprising the dimeric compound of claim 1 .
10. A composite comprising a substrate and the thin film semiconductor of claim 9 deposited on the substrate.
11. An organic field effect transistor device comprising the composite of claim 10 .