Organic semiconductor compositions

Abstract

The present invention relates to organic semiconductor compositions and organic semiconductor layers and devices comprising such organic semiconductor compositions. The invention is also concerned with methods of preparing such organic semiconductor compositions and layers and uses thereof. The invention has application particularly in the field of displays such as organic field effect transistors (OFETS), integrated circuits, organic light emitting diodes (OLEDS), photodetectors, organic photovoltaic (OPV) cells, sensors, lasers, memory elements and logic circuits.

1 . An organic semiconductor composition comprising a polyacene compound and an organic binder,
 wherein said polyacene compound is selected from those of Formulae (4) and (5):   
       
         
           
           
               
               
           
         
         
           wherein R 25 , R 26  and R 27  are independently selected from the group consisting of methyl, ethyl and isopropyl; and R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , R 10  and R 11  are independently selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy and C 6 -C 20  aryloxy, and wherein said organic binder is a semiconducting binder comprising a unit of Formula (6): 
         
       
       
         
           
           
               
               
           
         
         
           wherein Ar 1 , Ar 2  and Ar 3 , which may be the same or different, each represent, independently if in different repeat units, an optionally substituted C 6-40  aromatic group (mononuclear or polynuclear), wherein at least one of Ar 1 , Ar 2  and Ar 3  is substituted with at least one polar or more polarizing group, and n=1 to 20, and said organic binder has a permittivity at 1000 Hz of between 3.4 and 8.0, 
           with the proviso that the composition is not a composition containing components (a) and (b), wherein (a) is a 2,4-dimethoxy polytriarylamine polymer having a Mn of 3471 g/mol, in which n is 11.5, said polymer having a dielectric constant of 3.9 and a polydispersity of 2.6; and wherein (b) is 1,4,8,11-tetramethyl bis-triethylsilvylethynvylpentacene; wherein (a) and (b) are in a ratio of 2:1 in bromobenzene at 2% by weight total solids content. 
         
       
     
     
         2 . The composition according  claim 1 , wherein said binder has a permittivity at 1000 Hz of between 4.0 and 6.0. 
     
     
         3 . The composition according  claim 1 , wherein said binder has a permittivity at 1000 Hz of between 3.4 and 4.5. 
     
     
         4 - 16 . (canceled) 
     
     
         17 . The composition according to  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , R 10  and R 11  are independently selected from methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, methoxy, ethoxy, propyloxy and butyloxy groups. 
     
     
         18 . The composition according to  claim 1 , wherein R 1 , R 4 , R 8  and R 11  are the same and are methyl or methoxy groups and R 25 , R 26  and R 27  are the same and are ethyl or isopropyl groups. 
     
     
         19 . The composition according to  claim 18 , wherein R 1 , R 4 , R 8  and R 11  are methyl groups and R 25 , R 26  and R 27  are ethyl groups. 
     
     
         20 . The composition according to  claim 18 , wherein R 1 , R 4 , R 8  and R 11  are methyl groups and R 25 , R 26  and R 27  are isopropyl groups. 
     
     
         21 . The composition according to  claim 18 , wherein R 1 , R 4 , R 8  and R 11  are methoxy groups and R 25 , R 26  and R 27  are ethyl groups. 
     
     
         22 . The composition according to  claim 18 , wherein R 1 , R 4 , R 8  and R 11  are methoxy groups and R 25 , R 26  and R 27  are isopropyl groups. 
     
     
         23 . The composition according to  1 , wherein R 2 , R 3 , R 9  and R 10  are the same and are methyl or methoxy groups and R 25 , R 26  and R 27  are the same and are ethyl or isopropyl groups. 
     
     
         24 . The composition according to  claim 23 , wherein R 2 , R 3 , R 9  and R 10  are methyl groups and R 25 , R 26  and R 27  are ethyl groups. 
     
     
         25 . The composition according to  claim 23 , wherein R 2 , R 3 , R 9  and R 10  are methyl groups and R 25 , R 26  and R 27  are isopropyl groups. 
     
     
         26 . The composition according to  claim 23 , wherein R 2 , R 3 , R 9  and R 10  are methoxy groups and R 25 , R 26  and R 27  are ethyl groups. 
     
     
         27 . The composition according to  claim 23 , wherein R 2 , R 3 , R 9  and R 10  are methoxy groups and R 25 , R 26  and R 27  are isopropyl groups. 
     
     
         28 - 29 . (canceled) 
     
     
         30 . The composition according to  claim 1 , wherein said one or more polar or polarising group(s) on the organic binder is independently selected from the group consisting of nitro group, nitrile group, C 1-40  alkyl group substituted with a nitro group, a nitrile group, a cyanate group, an isocyanate group, a thiocyanate group or a thioisocyanate group; C 1-40  alkoxy group optionally substituted with a nitro group, a nitrile group, a cyanate group, an isocyanate group, a thiocyanate group or a thioisocyanate group; C 1-40  carboxylic acid group optionally substituted with a nitro group, a nitrile group, a cyanate group, an isocyanate group, a thiocyanate group or a thioisocyanate group; C 2-40  carboxylic acid ester optionally substituted with a nitro group, a nitrile group, a cyanate group, an isocyanate group, a thiocyanate group or a thioisocyanate group; sulfonic acid optionally substituted with a nitro group, a nitrile group, a cyanate group, an isocyanate group, a thiocyanate group or a thioisocyanate group; sulfonic acid ester optionally substituted with a nitro group, a nitrile group, a cyanate group, an isocyanate group, a thiocyanate group or a thioisocyanate group; cyanate group, isocyanate group, thiocyanate group, thioisocyanate group; and an amino group optionally substituted with a nitro group, a nitrile group, a cyanate group, an isocyanate group, a thiocyanate group or a thioisocyanate group; and combinations thereof. 
     
     
         31 . The composition according to  claim 1 , wherein said one or more polar or polarising group(s) is independently is selected from the group consisting of C 1-4  cyanoalkyl group, C 1-10  alkoxy group, nitrile group, amino group and combinations thereof. 
     
     
         32 . The composition according to  claim 1 , wherein the polar or polarizing group is selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, cyanomethyl, cyanoethyl, nitrile, NH 2  and combinations thereof. 
     
     
         33 . The composition according to any of  claim 1 , wherein Ar 1 , Ar 2  and Ar 3 , are independently selected from the group consisting of C 6-10  aryl, C 7-12  aralkyl and C 7-12  alkaryl, any of which may be substituted with 1, 2, or 3 groups independently selected from C 1-2  alkoxy, C 1-3  cyanoalkyl, CN and mixtures thereof, and n=1 to 10. 
     
     
         34 . The composition according to any of  claim 1 , wherein Ar 1 , Ar 2  and Ar 3  are all phenyl which may be independently substituted with 1 or 2 groups selected from methoxy, cyanomethyl and CN and mixtures thereof, and n=1 to 10. 
     
     
         35 . (canceled) 
     
     
         36 . The composition according to  claim 1 , wherein said organic binder comprises at least one unit selected from the following structures (G) to (J): 
       
         
           
           
               
               
           
         
       
     
     
         37 - 40 . (canceled) 
     
     
         41 . The composition according to  claim 1 , wherein said composition has a charge mobility value of at least 0.5 cm V −1  s −1 . 
     
     
         42 . The composition according to  claim 41 , wherein said composition has a charge mobility value of between 1.5 and 8.0 cm V −1  s −1 . 
     
     
         43 - 45 . (canceled) 
     
     
         46 . A method of forming the organic semiconductor layer according to  claim 1 , comprising the steps of:
 a. Mixing the organic semiconductor composition according to the present invention with a solvent to form a semiconductor layer formulation;   b. Depositing said formulation onto a substrate; and   c. Optionally removing the solvent to form an organic semiconductor layer.   
     
     
         47 - 51 . (canceled) 
     
     
         52 . An electronic device comprising the organic semiconductor composition or layer according to any of  claim 1 . 
     
     
         53 . The electronic device according to  claim 52 , wherein said device is selected from the group consisting of organic field effect transistors (OFETS), integrated circuits, organic light emitting diodes (OLEDS), photodetectors, organic photovoltaic (OPV) cells, sensors, lasers, memory elements and logic circuits. 
     
     
         54 . (canceled)