Compounds Having Semiconducting Properties and Related Compositions and Devices

Abstract

Disclosed are new compounds having semiconducting properties. Such compounds can be processed in solution-phase at a temperature of less than about 50° C. into thin film semiconductors that exhibit high carrier mobility and/or good current modulation characteristics.

1 - 24 . (canceled) 
     
     
         25 . A compound having formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         X is selected from S, O, and CH═CH; 
         Y is selected from S, O, and CH═CH; 
         Z is H or CHR 1 R 1 ′; 
         R′, R 1 ′, R 2 , and R 2 ′ independently are selected from a linear C 1-40  alkyl group, a linear C 2-40  alkenyl group, and a linear C 1-40  haloalkyl group; and 
         m, at each occurrence, independently is selected from 0, 1, 2, 3, and 4. 
       
     
     
         26 . The compound of  claim 25 , wherein the compound has the formula II: 
       
         
           
           
               
               
           
         
         wherein Z, R 2 , R 2 ′, and m are as defined in  claim 25 . 
       
     
     
         27 . The compound of  claim 25 , wherein the compound has the formula III: 
       
         
           
           
               
               
           
         
         wherein Z, R 2 , R 2 ′, and m are as defined in  claim 25 . 
       
     
     
         28 . The compound of  claim 25 , wherein the compound has the formula IV: 
       
         
           
           
               
               
           
         
         wherein Z, R 2 , R 2 ′, and m are as defined in  claim 25 . 
       
     
     
         29 . The compound of  claim 25 , wherein Z is CHR 1 R 1 ′, and each m independently is selected from 1, 2, and 3. 
     
     
         30 . The compound of  claim 29 , wherein R 1  and R 2  independently are selected from a linear C 3-40  alkyl group, a linear C 3-40  alkenyl group, and a linear C 3-40  haloalkyl group; and 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 . 
     
     
         31 . The compound of  claim 25 , wherein the compound has the formula IIa, IIIa, or IVa: 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  independently are selected from C 2 H 5 , n-C 3 H 7 , n-C 4 H 9 , n-C 5 H 11 , n-C 6 H 13 , n-C 7 H 15 , n-C 8 H 17 , n-C 9 H 19 , n-C 10 H 21 , n-C 11 H 23 , and n-C 12 H 25 ; and m 1  and m 2  independently are selected from 0, 1, and 2. 
     
     
         32 . The compound of  claim 25 , wherein the compound has the formula IIb, IIIb, IVb, IIc, IIIc, or IVc: 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  independently are selected from C 2 H 5 , n-C 3 H 7 , n-C 4 H 9 , n-C 5 H 11 , n-C 6 H 13 , n-C 7 H 15 , n-C 8 H 17 , n-C 9 H 19 , n-C 10 H 21 , n-C 11 H 23 , and n-C 12 H 25 ; and m 1  and m 2  independently are selected from 0, 1, and 2. 
     
     
         33 . The compound of  claim 25 , wherein the compound has the formula V, VI, or VII: 
       
         
           
           
               
               
           
         
       
       wherein R 2  is selected from a linear C 3-40  alkyl group, a linear C 3-40  alkenyl group, and a linear C 3-40  haloalkyl group; R 2 ′ is selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; and m 1  and m 2  independently are selected from 0, 1, and 2. 
     
     
         34 . The compound of  claim 25 , wherein the compound has the formula Va, VIa, VIIa, Vb, VIb, or VIIb: 
       
         
           
           
               
               
           
         
       
       wherein R 2  is selected from a linear C 3-40  alkyl group, a linear C 3-40  alkenyl group, and a linear C 3-40  haloalkyl group; R 2 ′ is selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; and m 1  and m 2  independently are selected from 0, 1, and 2. 
     
     
         35 . A thin film semiconductor comprising a compound of  claim 25 . 
     
     
         36 . An electronic device, an optical device, or an optoelectronic device comprising the thin film semiconductor of  claim 35 . 
     
     
         37 . A field effect transistor device comprising a source electrode, a drain electrode, a gate electrode, and the thin film semiconductor of  claim 35  in contact with a dielectric material. 
     
     
         38 . The field effect transistor device of  claim 37 , 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. 
     
     
         39 . The field effect transistor device of  claim 37 , wherein the dielectric material comprises an organic dielectric material. 
     
     
         40 . The field effect transistor device of  claim 37 , wherein the dielectric material comprises an inorganic dielectric material or a hybrid organic/inorganic dielectric material. 
     
     
         41 . A light emitting transistor device comprising a source electrode, a drain electrode, a gate electrode, a dielectric material, and a photoactive component comprising a compound of  claim 25 , wherein the photoactive component is in contact with the dielectric material. 
     
     
         42 . The light emitting transistor device of  claim 41 , wherein the photoactive component comprises a laminate of two or more layers. 
     
     
         43 . The light emitting transistor device of  claim 42 , wherein the laminate comprises a light emitting layer and one or more organic charge transport layers. 
     
     
         44 . The light emitting transistor device of  claim 41 , wherein the compound of  claim 25  is present in a blend material.