Diketopyrrolopyrrole polymers for use in organic field effect transistors

Abstract

The present invention relates to polymers comprising a repeating unit of the formula I, or III and their use as organic semiconductor in organic devices, especially an organic field effect transistor (OFET), or a device containing a diode and/or an organic field effect transistor. The polymers according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers according to the invention are used in organic field effect transistors.

1 .- 16 . (canceled) 
     
     
         17 . A copolymer comprising repeating units of formula (VII) 
       
         
           
           
               
               
           
         
         wherein 
         A is a group of formula 
       
       
         
           
           
               
               
           
         
         COM 1  is a group of formula 
       
       
         
           
           
               
               
           
         
         a is an integer of 1 to 5, 
         n is number which results in a molecular weight of 4,000 to 2,000,000 Daltons, 
         Ar 1  and Ar 1′  are a group of formula 
       
       
         
           
           
               
               
           
         
         Ar 2  is a group of formula 
       
       
         
           
           
               
               
           
         
         one of X 1  and X 2  is N and the other is CH, and 
         R 1  and R 2  are the same or different and are selected from H or a C 1 -C 100 alkyl group. 
       
     
     
         18 . The copolymer according to  claim 17 , wherein a is an integer of 1 to 3. 
     
     
         19 . The copolymer according to  claim 17 , wherein R 1  and R 2  are a C 1 -C 100 alkyl group. 
     
     
         20 . The copolymer according to  claim 19 , wherein R 1  and R 2  are a C 8 -C 36 alkyl group. 
     
     
         21 . The copolymer according to  claim 17 , wherein Ar 2  is a group of formula 
       
         
           
           
               
               
           
         
       
     
     
         22 . A copolymer comprising repeating units of formula (IIa′) or (IIi) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are the same or different and are selected from a C 8 -C 36 alkyl group. 
       
     
     
         23 . The copolymer according to  claim 17 , which has a weight average molecular weight of 10,000 to 1,000,000 Daltons. 
     
     
         24 . The copolymer according to  claim 23 , which has a weight average molecular weight of 10,000 to 100,000 Daltons. 
     
     
         25 . A semiconductor device comprising the copolymer according to  claim 17 . 
     
     
         26 . The semiconductor device according to  claim 25  is an organic field effect transistor. 
     
     
         27 . A process for preparing an organic semiconductor device, the process comprising:
 applying a solution and/or dispersion comprising the copolymer according to  claim 17  in an organic solvent to a substrate; and   removing the solvent.   
     
     
         28 . An integrated circuit comprising the organic field effect transistor according to  claim 26 . 
     
     
         29 . A process for preparing the copolymer of  claim 17  comprising:
 reacting a dihalogenide X 10 -A-X 10  with an equimolar amount of a diboronic acid or diboronate corresponding to formula 
 
       
         
           
           
               
               
           
         
       
       or
 reacting a dihalogenide of formula 
 
       
         
           
           
               
               
           
         
       
       with an equimolar amount of a diboronic acid or diboronate corresponding to formula X 11 -A-X 11 ,
 wherein X 10  is halogen, and 
 X 11  is independently in each occurrence —B(OH) 2 , —B(OY 1 ) 2 , 
 
       
         
           
           
               
               
           
         
       
       —BF 3 Na, —BF 3 N(Y 15 ) 4 , or —BF 3 K, wherein Y 1  is independently in each occurrence a C 1 -C 10 alkyl group and Y 2  is independently in each occurrence a C 2 -C 10 alkylene group, Y 13  and Y 14  are independently of each other hydrogen, or a C 1 -C 10 alkyl group, Y 15  is H, or a C 1 -C 25 alkyl group, which may optionally be interrupted by —O—, in a solvent and in the presence of a catalyst; or
 reacting a dihalogenide of formula X 10 -A-X 10  with an equimolar amount of an organo tin compound corresponding to formula or 
 
       
         
           
           
               
               
           
         
       
       or
 reacting a dihalogenide of formula 
 
       
         
           
           
               
               
           
         
       
       with an equimolar amount of an organo tin compound corresponding to formula X 11′ -A-X 11′ , wherein 
       X 11′  is independently in each occurrence —SnR 207 R 208 R 209 , wherein R 207 , R 208  and R 209  are identical or different and are H or C 1 -C 6 alkyl, or two of the groups R 207 R 208  and R 209  form a ring and these groups are optionally branched. 
     
     
         30 . The process according to  claim 29 , wherein X 10  is Br.