Organic semiconductor material

Abstract

Novel compounds useful as organic semiconductor material are described. Semiconductor devices containing said organic semiconductor material are also described.

1 . A compound having formula selected in the group consisting of formula (I), formula (II), formula (III) and formula (IV): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1 , R 2 , R 2′  independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40  linear or branched alkyl groups, C 1 -C 40  linear or branched heteroalkyl groups, C 3 -C 40  linear or branched cycloalkyl groups, C 1 -C 40  linear or branched hydroxyalkyl groups, C 1 -C 40  linear or branched alkoxyl groups, C 1 -C 40  linear or branched alkylcarboxylic groups, C 1 -C 40  linear or branched alkylcarboxyamide groups, C 1 -C 40  linear or branched alkylsulphonic groups, and C 1 -C 40  linear or branched nitrile groups; 
 Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups; 
 Ar′, Ar″, independently of each other, are selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups; 
 n, r, independently of each other, are integers between 1 and 50; and 
 p is an integer between 0 and 5; 
 
       with the exception of compounds of formula A: 
       
         
           
           
               
               
           
         
         wherein R 4  is selected in the group consisting of C 1 -C 4  alkyls; and R 5  is selected in the group consisting of monocyclic aryl groups and substituted monocyclic aryl groups; 
         with the exception of the compound of formula 132: 
       
       
         
           
           
               
               
           
         
         and with the exception of compounds of formula B: 
       
       
         
           
           
               
               
           
         
         wherein R 6  is selected in the group consisting of isopropyl, cyclopropyl and terbutyl groups and R 7  is selected in the group consisting of phenyl, 2-fluorphenyl, 3-fluorphenyl, 4-fluorphenyl, 2-chlorphenyl, 3-chlorphenyl, 4-chlorphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl. 
       
     
     
         2 . The compound according to  claim 1 , wherein when p is 0, n is between 2 and 50. 
     
     
         3 . The compound according to  claim 1 , having formula selected in the group consisting of formula (Ia), formula (IIa), formula (IIIa) and formula (IVa) 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1 , R 2 , independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40  linear or branched alkyl groups, C 1 -C 40  linear or branched heteroalkyl groups, C 3 -C 40  linear or branched cycloalkyl groups, C 1 -C 40  linear or branched hydroxyalkyl groups, C 1 -C 40  linear or branched alkoxyl groups, C 1 -C 40  linear or branched alkylcarboxylic groups, C 1 -C 40  linear or branched alkylcarboxyamide groups, C 1 -C 40  linear or branched alkylsulphonic groups, and C 1 -C 40  linear or branched nitrile groups; 
 Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl group and polycyclic heteroaryl group; 
 Ar′ is a moiety selected in the group consisting of a monocyclic aryl group, polycyclic aryl group, monocyclic heteroaryl group and polycyclic heteroaryl group. 
 
     
     
         4 . The compound according to  claim 3 , wherein Ar is selected in the group consisting of the following rings (f), (g), (h), (i), (l), (m), (n), (o), (p): 
       
         
           
           
               
               
           
         
       
       wherein X is selected in the group consisting of S, O, Si, Se, NR 3 ,
 R 3  being selected in the group consisting of C 1 -C 12  linear or branched alkyl groups, C 1 -C 12  linear or branched halogenoalkyl groups, C 3 -C 12  linear or branched cycloalkyl groups, C 1 -C 12  linear or branched hydroxyalkyl groups, C 1 -C 12  linear or branched alkoxyl groups, C 1 -C 12  linear or branched alkylcarboxylic groups, C 1 -C 12  linear or branched alkylcarboxyamide groups, C 1 -C 12  linear or branched alkylsulphonic groups, and C 1 -C 12  linear or branched nitrile groups. 
 
     
     
         5 . The compound according to  claim 1 , wherein R 1 , R 2 , independently of each other, are selected in the group consisting of C 1 -C 12  linear or branched alkyl groups, C 1 -C 12  linear or branched heteroalkyl groups, C 3 -C 12  linear or branched cycloalkyl groups, C 1 -C 12  linear or branched hydroxyalkyl groups, C 1 -C 12  linear or branched alkoxyl groups, C 1 -C 12  linear or branched alkylcarboxylic groups, C 1 -C 12  linear or branched alkylcarboxyamide groups, C 1 -C 12  linear or branched alkylsulphonic groups, and C 1 -C 12  linear or branched nitrile groups. 
     
     
         6 . The compound according to  claim 1 , wherein Ar′ is a unit selected in the group consisting of the following units (a), (b), (c): 
       
         
           
           
               
               
           
         
       
       wherein W is selected in the group consisting of S, SO and SO 2 ;
 Y is selected in the group consisting of S, O, NR 8 ; and 
 R 6 , R 7 , and R 8  independently of each other, are selected in the group consisting of hydrogen, C 1 -C 12  linear or branched alkyl groups, C 1 -C 12  linear or branched halogenoalkyl groups, C 3 -C 12  linear or branched cycloalkyl groups, C 1 -C 12  linear or branched hydroxyalkyl groups, C 1 -C 12  linear or branched alkoxyl groups, C 1 -C 12  linear or branched alkylcarboxylic groups, C 1 -C 12  linear or branched alkylcarboxyamide groups, C 1 -C 12  linear or branched alkylsulphonic groups, and C 1 -C 12  linear or branched nitrile groups. 
 
     
     
         7 . The compound according to  claim 1  having the following formula (V): 
       
         
           
           
               
               
           
         
       
       wherein R 4 , R 5 , independently of each other, are selected in the group consisting of C 1 -C 8  linear or branched saturated alkyl groups, C 1 -C 8  linear or branched fluoroalkyl groups, C 1 -C 8  linear or branched heteroalkyl groups comprising a heteroatom selected among O, S, N; and 
       m is an integer between 1 and 30. 
     
     
         8 . The compound according to  claim 7 , having formula (VI): 
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound according to  claim 1 , having the following formula (VII): 
       
         
           
           
               
               
           
         
         wherein R 4 , R 5 , independently of each other, are selected in the group consisting of C 1 -C 8  linear or branched saturated alkyl groups, C 1 -C 8  linear or branched fluoroalkyl groups, C 1 -C 8  linear or branched heteroalkyl groups comprising a heteroatom selected among O, S, N. 
       
     
     
         10 . A process for the preparation of the compound according to  claim 1 , comprising:
 subjecting a reaction mixture comprising a reaction medium and an halogenated aromatic halide to:
 a Stille coupling reaction with an organotin compound; or 
 to a Suzuki coupling reaction with an organoboron compound. 
   
     
     
         11 . A method comprising:
 using a compound having formula selected in the group consisting of formula (I), formula (II), formula (III) and formula (IV):   
       
         
           
           
               
               
           
         
       
       wherein:
 R 1 , R 2 , R 2′  independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40  linear or branched alkyl groups, C 1 -C 40  linear or branched heteroalkyl groups, C 3 -C 40  linear or branched cycloalkyl groups, C 1 -C 40  linear or branched hydroxyalkyl groups, C 1 -C 40  linear or branched alkoxyl groups, C 1 -C 40  linear or branched alkylcarboxylic groups, C 1 -C 40  linear or branched alkylcarboxyamide groups, C 1 -C 40  linear or branched alkylsulphonic groups, and C 1 -C 40  linear or branched nitrile groups; 
 Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups; 
 Ar′, Ar″, independently of each other, are selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups;
 n, r, independently of each other, are integers between 1 and 50; and 
 p is an integer between 0 and 5; 
 
 
       as an organic semiconductor material in an electronic device. 
     
     
         12 . A method comprising:
 using the compound according to  claim 2  as an organic semiconductor material in an electronic device.   
     
     
         13 . The method according to  claim 11 , wherein the organic semiconductor material is an n-type organic semiconductor material. 
     
     
         14 . An electronic device comprising a semiconductor layer in contact with a number of electrodes, wherein the semiconductor layer includes at least one compound having formula selected in the group consisting of formula (I), formula (II), formula (III) and formula (IV): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1 , R 2 , R 2′  independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40  linear or branched alkyl groups, C 1 -C 40  linear or branched heteroalkyl groups, C 3 -C 40  linear or branched cycloalkyl groups, C 1 -C 40  linear or branched hydroxyalkyl groups, C 1 -C 40  linear or branched alkoxyl groups, C 1 -C 40  linear or branched alkylcarboxylic groups, C 1 -C 40  linear or branched alkylcarboxyamide groups, C 1 -C 40  linear or branched alkylsulphonic groups, and C 1 -C 40  linear or branched nitrile groups; 
 Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups; 
 Ar′, Ar″, independently of each other, are selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups; 
 n, r, independently of each other, are integers between 1 and 50; and 
 p is an integer between 0 and 5. 
 
     
     
         15 . An electronic device comprising a semiconductor layer in contact with a number of electrodes, wherein the semiconductor layer includes at least one compound according to  claim 2 .