Compound with branching alkyl chains, method for preparing the same, and use thereof in photoelectric device

Abstract

The invention discloses a compound having branching alkyl chains, the method for preparing the same and use thereof in photoelectric devices. By applying the branching alkyl chains as the solubilizing group to the preparation of organic conjugated molecules (for example, organic conjugated polymers), the number of methylenes between the resultant alkyl side chains and the backbone, i.e., m>1, which can effectively reduce the effect of the alkyl chains on the backbone π-π stacking, thereby ensuring the solubility of the organic conjugated molecule while greatly increasing the mobility of their carriers. It is suitable for an organic semiconductor material in photoelectric devices such as organic solar cells, organic light emitting diodes and organic field effect transistors, etc.

1 . A Formula (I) compound: 
       
         
           
           
               
               
           
         
         in the structure of Formula (I), m is an integer from 3 to 18; R is a halogen atom, hydroxyl, amino, trifluoromethanesulfonate group, p-toluenesulfonate group, azide group, cyano, alkenyl, alkynyl or alkoxy; R 3  and R 4  are the same or different, independently selected from alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl and alkynyl; R 5  is hydrogen, hydroxyl, alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl or alkynyl. 
       
     
     
         2 . The Formula (I) compound according to  claim 1 , wherein m is an integer from 3 to 4. 
     
     
         3 . The Formula (I) compound according to  claim 1 , wherein the compound is selected from one of the following compounds: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The method for preparation the Formula (I) compound according to  claim 1  comprising the following steps:
 1) Starting from the diol as shown in Formula (a), protection by a protecting group is conducted to obtain the diol with one terminus protected as shown in Formula (b); 
 
       
         
           
           
               
               
           
         
         2) The diol with one terminus protected is oxidized to obtain the carboxylic acid as shown in Formula (c); 
       
       
         
           
           
               
               
           
         
         3) The carboxylic acid as shown in Formula (c) is subject to functional group transformation and nucleophilic substitution to introduce the R 3  and R 4  groups; 
       
       
         
           
           
               
               
           
         
         4) R 5  is introduced; 
       
       
         
           
           
               
               
           
         
         5) The protecting group is eliminated to generate the corresponding alcohol; 
       
       
         
           
           
               
               
           
         
         6) When the R in Formula (I) is not hydroxyl, a substitution is conducted on the hydroxyl in the Formula (k) compound to convert it to other functional group, obtaining the Formula (1) compound with R being the corresponding functional group, wherein m−1 is an integer of from 3 to 18 or from 3 to 4; R 3  and R 4  are the same or different, independently selected from alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl and alkynyl; R 5  is hydrogen, hydroxyl, alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl or alkynyl. 
       
     
     
         5 . The method of preparation according to  claim 4 , wherein the step 3) is conducted with the following method 3a) or 3b):
 3a) The carboxylic acid is reacted with an alcohol and converted into an ester, followed by a nucleophilic substitution to introduce the R 3  and R 4  groups:   
       
         
           
           
               
               
           
         
         wherein R 1  is alkyl; 
         3b) The carboxylic acid is converted to an acyl halide, then the nucleophilic substitution is conducted to introduce the R 3  and R 4  groups: 
       
       
         
           
           
               
               
           
         
         wherein X is halogen, 
         wherein m−1 is an integer of from 3 to 18 or from 3 to 4; R 3  and R 4  are the same or different, independently selected from alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl and alkynyl. 
       
     
     
         6 . The method of preparation according to  claim 4 , wherein the step 4) is conducted with the following method 4a), 4b) or 4c):
 4a) When R 5  is alkoxy, a strong alkaline is reacted with the alcohol hydroxyl of the Formula (e) compound to generate an oxygen anion, which is subsequently subject to a nucleophilic substutition by R 5 ′X to obtain the compound of Formula (g):   
       
         
           
           
               
               
           
         
         wherein OR 5 ′ is R 5 ; X is a halogen atom, trifluoromethanesulfonate group or p-toluenesulfonate group; and R 5 ′ is alkyl; 
         4b) When R 5  is alkyl, halogen substituted alkoxy, alkenyl or alkynyl, the Formula (e) compound is reacted with trifluoromethanesulfonyl chloride to generate trifluoromethanesulfonate group, and then a nucleophilic substitution is conducted to obtain the Formula (i) compound: 
       
       
         
           
           
               
               
           
         
         4c) When R 5  is hydrogen atom, the oxygen atom is removed under the conditions of triethylsilane and trifluoroacetic acid to form the Formula (j) compound, 
       
       
         
           
           
               
               
           
         
       
       wherein m−1 is an integer of from 3 to 18 or from 3 to 4; R 3  and R 4  are the same or different, independently selected from alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl and alkynyl. 
     
     
         7 . The method of preparation according to  claim 4 , wherein the step 6) is conducted using one of the following method 6a)˜6f) depending on different substituents of R:
 6a) When R is halogen, one of the following reactions is conducted to obtain the corresponding Formula (I) compound: 
 
       
         
           
           
               
               
           
         
         6b) When R is trifluoromethanesulfonate group or p-toluenesulfonate group, an alkaline is reacted with the alcohol hydroxyl to generate an oxygen anion, which is subsequently subject to a nucleophilic substutition by MsCl or TsCl to obtain the corresponding Formula (1) compound; 
       
       
         
           
           
               
               
           
         
         6c) When R is an azide group, the Formula (I) compound with R being an azide group is obtained by a nucleophilic substitution between sodium azide and halogen, trifluoromethanesulfonate group or p-toluenesulfonate group: 
       
       
         
           
           
               
               
           
         
         In the aforementioned reaction, X represents a halogen atom, trifluoromethanesulfonate group or p-toluenesulfonate group; 
         6d) When R is cyano, the Formula (I) compound with R being a cyano is obtained by a nucleophilic substitution between a cyanide and halogen, trifluoromethanesulfonate group or p-toluenesulfonate group: 
       
       
         
           
           
               
               
           
         
         In the aforementioned reaction, X represents a halogen atom, trifluoromethanesulfonate group or p-toluenesulfonate group; 
         6e) When R is amino, the Formula (I) compound with R being an amino is obtained by that the azide group or cyano is reduced to amino, or a Gabriel amine synthesis: 
       
       
         
           
           
               
               
           
         
         In the aforementioned reaction, X represents a halogen atom, trifluoromethanesulfonate group or p-toluenesulfonate group; 
         6f) When R is an alkenyl or alkynyl, the Formula (1) compound with R being alkenyl or alkynyl is obtained by a nucleophilic substitution of the Formula (I) compound with R being a halogen atom by a nucleophilic agent containing the alkenyl or alkynyl, 
         wherein m−1 is an integer of from 3 to 18 or from 3 to 4; R 3  and R 4  are the same or different, independently selected from alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl and alkynyl; R 5  is hydrogen, hydroxyl, alkyl, halogen substituted alkyl, alkoxy, halogen substituted alkoxy, alkenyl or alkynyl.