Electronic device comprising an organic semiconducting material

Abstract

The present invention relates to an electronic device comprising at least one organic semiconducting material according to the following formula (I): wherein R 1-4 are independently selected from H, halogen, CN, substituted or unsubstituted C 1 -C 20 -alkyl or heteroalkyl, C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, C 1 -C 20 -alkoxy or C 6 -C 20 -aryloxy, Ar is selected from substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, and R5 is selected from substituted or unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, H, F or formula (II).

The invention claimed is: 
     
       1. An electronic device comprising at least one organic semiconducting material according to formula (I): 
       
         
           
           
               
               
           
         
         wherein R 1-4  are independently selected from H, halogen, CN, C 1 -C 20 -alkyl, C 1 -C 20 -heteroalkyl, C 6 -C 20 -aryl, C 5 -C 20 -heteroaryl, C 1 -C 20 -alkoxy, or C 6 -C 20 -aryloxy, wherein each C 1 -C 20 -alkyl, C 1 -C 20 -heteroalkyl, C 6 -C 20 -aryl, C 5 -C 20 -heteroaryl, C 1 -C 20  alkoxy, or C 6 -C 20 -aryloxy is unsubstituted or substituted, 
         wherein Ar is selected from, substituted or unsubstituted, C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, and 
         R 5  is selected from substituted or unsubstituted C 6 -C 20 -aryl, substituted or unsubstituted C 5 -C 20 -heteroaryl, H, F, or 
       
       
         
           
           
               
               
           
         
         wherein R 1-4 , are as previously defined; 
         wherein the device has a layered structure and at least one layer comprises at least one compound according to formula (I). 
       
     
     
       2. The electronic device according to  claim 1 , wherein Ar and R 1-4  are independently selected from C 6 -C 20  aryl or C 5 -C 20 -heteroaryl. 
     
     
       3. The electronic device according to  claim 1 , wherein R 5  is H or F, and R 5  and Ar are a moiety selected from 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       4. The electronic device according to  claim 1 , wherein Ar is selected from 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       5. The electronic device according to  claim 1 , wherein the organic semiconducting material is doped by an n-dopant. 
     
     
       6. The electronic device according to  claim 5 , wherein the organic semiconducting material is doped by an organic n-dopant having a HOMO energy level which is more positive than −3.3 eV. 
     
     
       7. The electronic device according to  claim 1 , wherein the device is an electronic, optoelectronic or electroluminescent device having an electronically functionally effective region, wherein the electronically effective region comprises at least one compound according to formula (I). 
     
     
       8. The electronic device according to  claim 1 , wherein the device is an organic light-emitting diode, a field-effect transistor, a sensor, a photodetector, an organic thin-film transistor, an organic integrated circuit, an organic light-emitting transistor, a light-emitting electrochemical cell, or an organic laser diode. 
     
     
       9. A compound according to formula (I): 
       
         
           
           
               
               
           
         
         wherein R 1-4  are independently selected from H, halogen, CN, C 1 -C 20 -alkyl, C 1 -C 12 20-heteroalkyl, C 6 -C 20 -aryl, C 5 -C 20 -heteroaryl, C 1 -C 20 -alkoxy, or C 6 -C 20 aryloxy, wherein each C 1 -C 20 -alkyl, C 1 -C 20 -heteroalkyl, C 1 -C 20 -aryl, C 5 -C 20 -heteroaryl, C 1 -C 20 -alkoxy, or C 6 -C 20 -aryloxy is unsubstituted or substituted, 
         wherein R 5  is H, and Ar is 
       
       
         
           
           
               
               
           
         
       
       
        
         wherein Ar is selected from unsubstituted C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, and 
         wherein R 5  is selected from F, substituted or unsubstituted C 6 -C 20 -aryl, substituted or unsubstituted C 5 -C 20 -heteroaryl in which one or two carbon atoms is substituted by N or S, 
       
       
         
           
           
               
               
           
         
         wherein R 1 -R 4  are as previously defined, 
       
       
         
           
           
               
               
           
         
        
       
     
     
       10. A compound according to formula (I): 
       
         
           
           
               
               
           
         
         wherein R 1-4  are independently selected from H, halogen, CN, C 1 -C 20 -alkyl, C 1 -C 20 -heteroalkyl, C 6 -C 20 -aryl, C 5 -C 20 -heteroaryl, C 1 -C 20 -alkoxy, or C 6 -C 20 -aryloxy, wherein each C 1 -C 20 -alkyl, C 1 -C 20 -heteroalkyl, C 6 -C 20 -aryl, C 5 -C 20 -heteroaryl, C 1 -C 20 -alkoxy, or C 6 -C 20 -aryloxy is unsubstituted or substituted, 
         wherein Ar is selected from, substituted or unsubstituted, C 6 -C 20 -aryl or C 5 -C 20 -heteroaryl, and 
         wherein R 5  is H or F and combines with Ar to a moiety selected from 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
        
       
     
     
       11. A compound having one of the following structures: