Self-assembled monolayer for electrode modification and device comprising such self-assembled monolayer

Abstract

The present application relates to a self-assembled monolayer suitable for the modification of electrodes comprised in electronic devices as well as to such electronic devices. The present application also relates to a method for depositing such self-assembled monolayer onto an electrode as well as to the manufacturing of the corresponding devices.

1 .- 14 . (canceled) 
     
     
         15 . An organic electronic device comprising an electrode, a self-assembled monolayer on said electrode and an organic semiconducting layer on said self-assembled monolayer, wherein said self-assembled monolayer is formed by depositing the reaction product of a compound of the following formula (I
   R 1 —SiX 3   (I)
   
       and an alcohol of formula R 2 —OH onto said electrode, 
       with
 R 1  being at each occurrence independently alkyl having from 1 to 10 carbon atoms, said alkyl being substituted with at least one electron-withdrawing group R A , or aryl having from 6 to 30 aromatic carbon ring atoms, said aryl being substituted with at least one electron-withdrawing group; 
 R 2  being an alkyl group having from 1 to 10 carbon atoms; and 
 X being at each occurrence independently halogen or alkoxy having from 1 to 10 carbon atoms. 
 
     
     
         16 . The organic electronic device according to  claim 15 , wherein the self-assembled monolayer is formed by depositing the formulation comprising the compound of formula (I) and the alcohol of formula R 2 —OH onto the electrode. 
     
     
         17 . The organic electronic device according to  claim 15 , wherein R 1  is at each occurrence independently a group select of any of the following formulae (II-a) or (II-b) 
       
         
           
           
               
               
           
         
       
       wherein
 b is at each occurrence independently an integer of at least 1 and of at most 10; 
 c is at each occurrence an integer of at least 1 and at most 2b+1; 
 d is at each occurrence an integer of at least 0 and at most 2b; 
 with the provision that the sum of c and d is 2b+1; and 
 e is at each occurrence independently an integer of at least 1 and of at most 5. 
 
     
     
         18 . The organic electronic device according to  claim 17 , wherein c is 2b+1. 
     
     
         19 . The organic electronic device according to  claim 17 , wherein e is 5. 
     
     
         20 . The organic electronic device according to  claim 15 , wherein R A  is at each occurrence independently selected from the group consisting of —NO 2 , —CN, —F, —Cl, —Br, —I, —OAr 2 , —OR 3 , —COR 3 , —SH, —SR 3 , —OH, —C≡CR 3 , —CH═CR 3   2 , and alkyl having from 1 to 10 carbon atoms, wherein one or more, preferably all, hydrogen atoms are replaced by F, with Ar 2  being at each occurrence independently an aryl having from 6 to 30 carbon atoms, and R 3  being at each occurrence independently an alkyl having from 1 to 10 carbon atoms or an alkyl having from 1 to 10 carbon atoms wherein one or more hydrogen atom is replaced by F. 
     
     
         21 . The organic electronic device according to  claim 15 , wherein R A  is F. 
     
     
         22 . The organic electronic device according to  claim 15 , wherein the compound of formula (I) is selected from the group consisting of the following formulae (I-1) to (I-11) 
       
         
           
           
               
               
           
         
       
       wherein e is an integer of at least 1 and at most 10. 
     
     
         23 . The organic electronic device according to  claim 15 , wherein the electrode is an indium tin oxide electrode. 
     
     
         24 . The organic electronic device according to  claim 15 , wherein R 2  is an alkyl having from 1 to 5 carbon atoms. 
     
     
         25 . The organic electronic device according to  claim 15 , wherein R 2  is iso-propyl. 
     
     
         26 . The organic electronic device according to  claim 15 , said organic electronic device being selected from the group consisting of organic field effect transistors (OFET), organic thin film transistors (OTFT), organic light emitting diodes (OLED), organic light emitting transistors (OLET), organic photovoltaic devices (OPV), organic photodetectors (OPD), organic solar cells, laser diodes, Schottky diodes, photoconductors and photodetectors. 
     
     
         27 . The organic electronic device according to  claim 15 , said organic electronic device being an organic field effect transistor (PFET) or an organic thin film transistor (OTFT). 
     
     
         28 . A method of producing the organic electronic device of  claim 15 , said method comprising the steps of
 (a) providing an electrode, optionally on a substrate;   (b) depositing onto said electrode a formulation comprising a compound of formula (I)
   R 1 —SiX 3   (I)
 
 and an alcohol of formula R 2 —OH, 
   with
 R 1  being at each occurrence independently alkyl having from 1 to 10 carbon atoms, said alkyl being substituted with at least one electron-withdrawing group R A , or aryl having from 6 to 30 aromatic carbon ring atoms, said aryl being substituted with at least one electron-withdrawing group R A ; 
 R 2  being an alkyl group having from 1 to 10 carbon atoms; and 
 X being at each occurrence independently halogen or alkoxy having from 1 to 10 carbon atoms, 
 to obtain a self-assembled monolayer; and 
   (c) depositing onto said self-assembled monolayer an organic semiconducting material to obtain an organic semiconducting layer.   
     
     
         29 . The method according to  claim 28 , wherein R 1  is at each occurrence independently a group select of any of the following formulae (II-a) or (II-b) 
       
         
           
           
               
               
           
         
       
       wherein
 b is at each occurrence independently an integer of at least 1 and of at most 10; 
 c is at each occurrence an integer of at least 1 and at most 2b+1; 
 d is at each occurrence an integer of at least 0 and at most 2b; 
 with the provision that the sum of c and d is 2b+1; and 
 e is at each occurrence independently an integer of at least 1 and of at most 5; 
 wherein R 2  in the alcohol R 2 —OH is an alkyl having from 1 to 5 carbon atoms; and the electrode is an indium tin oxide electrode.