Method of doping organic semiconductors with quinone derivatives and 1, 3, 2 - dioxaborine derivatives

Abstract

The invention relates to the use of an organic mesomeric compound as organic dopant for doping an organic semiconducting matrix material for varying the electrical properties thereof. In order to be able to handle organic semiconductors more easily in the production process and to be able to produce electronic components with doped organic semiconductors more reproducibly, a quinone or quinone derivative or a 1,3,2-dioxaborine or a 1,3,2-dioxaborine derivative may be used as a mesomeric compound, which under like evaporation conditions has a lower volatility than tetrafluorotetracyanoquinonedimethane (F4TCNQ).

1 - 54 . (canceled)  
     
     
         55 . Dopand for doping an organic semiconducting matrix material, wherein the dopand is an organic, mesomeric quinon or quinon derivative compound selected from the group consisting of compounds having one of the following structures:  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein in structure (40) R 1 -R 4  is independently Cl, CN, aryl or heteroary, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , CF 3 , perfluoroalkyl, SO 3 R and halogen, wherein A and B are selected from  
       
         
           
           
               
               
           
         
       
       wherein in structure (41) R 1 -R 8  is independently Cl, F, CN, NO 2 , perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , NO, perfluoroalkyl, S0 3 R, and halogen; 
 wherein in structure (42) R 1 -R 6  is independently Cl, F, CN, NO 2 , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, SO 3 R and halogen, wherein A and B are selected from the group consisting of  
                     
 wherein in structure (43) R 1 -R 8  is independently Cl, F, perfluoroalkyl, CN, NO 2 , NO, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, SO 3 R and halogen;  
 wherein in structure (44) R 1 -R 6  is independently Cl, F, CN, NO 2 , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, SO 3 R and halogen;  
 wherein in structure (45) R 1 -R 4  is independently Cl, F, NO 2 , NO, perfluoroalkyl, aryl, or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, SO 3 R and halogen;  
 wherein in structure (46) R 1 -R 6  is independently Cl, F, CN, NO 2 , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, S0 3 R and halogen;  
 wherein in structure (47) R 1 -R 12  is independently Cl, F, CN, NO 2 , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, SO 3 R and halogen, or wherein R 1 , R 3 , R 9  and R 12  are hydrogen and R 2 , R 4 -R 8 , R 10  and R 11  is independently Cl, F, CN, NO 2 , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, SO 3 R and halogen;  
 wherein in structure (48) R 1 -R 12  is independently Cl, F, CN, NO 2 , NO, perfluoroalkyl, aryl or heteroaryl, wherein aryl and heteroaryl have one or more substituents selected from the group consisting of CN, NO 2 , perfluoroalkyl, SO 3 R and halogen;  
 and wherein the dopand, under like evaporation conditions, has a lower volatility than tetrafluorotetracyano-quinonedimethane (F 4 TCQ).  
 
     
     
         56 . Dopand according to  claim 55 , wherein the substituents A, B, C and D in structures (41), and (43) to (48) are the same or different and are selected from the group consisting of:  
       
         
           
           
               
               
           
         
       
     
     
         57 . Dopand according to  claim 55  or  56 , wherein perfluoroalkyl is CF 3 , and halogen is fluorine or chlorine.  
     
     
         58 . Dopand according to  claim 55 , wherein the dopand is a quinoid system having a quinoid ring and one, two or three annulated aromatic rings.  
     
     
         59 . Dopand according to  claim 58 , wherein the aromatic rings have one or more hetero atoms.