Organic semiconductor material, organic semiconductor thin film and organic semiconductor device

Abstract

An organic semiconductor material is provided. The organic semiconductor material includes a polyacene derivative expressed by the following general formula (1): where each of R 1 to R 10 may be independently the same substituents or different substituents but all of R 1 , R 4 , R 5 , R 6 , R 9 and R 10 may never be hydrogen atoms at the same time, and where each of R 1 to R 10 is at least one kind of substituent selected from the group consisting of an aliphatic hydrocarbon group having a substituent and of which number of carbon atoms ranges of from 1 to 20, an aromatic hydrocarbon group having a substituent, a complex aromatic group having a substituent, a carboxyl group, a hydride, an ester group, a cyano group, a hydroxyl group, a halogen atom and a hydrogen atom. The organic semiconductor material can be dissolved into an organic solvent at low temperature (for example, room temperature) and is suitable for use with a coating process.

1 . An organic semiconductor material consisting of a polyacene derivative expressed by the following general formula (1): 
       
         
           
           
               
               
           
         
       
       wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9  and R 10  may be independently the same substituents or different substituents but all of R 1 , R 4 , R 5 , R 6  and R 10  may never be hydrogen atoms at the same time; and
 wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9  and R 10  is at least one kind of substituent selected from the group consisting of an aliphatic hydrocarbon group having a substituent and of which number of carbon atoms ranges from 1 to 20, an aromatic hydrocarbon group having a substituent, a complex aromatic group having a substituent, a carboxyl group, a hydride, an ester group, a cyano group, a hydroxyl group, a thiocarboxyl group, a dithiocarboxyl group, a sulfonic acid group, a sulfinic acid group, a sulfenic acid group, a sulfonyl group, a sulfinyl group, an acyl halide group, a carbamoyl group, a hydrazide group, an imide group, an amide group, an amidino group, an isocyano group, a cyanic acid ester group, an isocyanic acid ester group, a thiocyanic acid ester group, an isothiocyanic acid ester group, a formyl group, a thioformyl group, an acyl group, a thiol group, an amino group, an imino group, a hydrazino group, an alkoxy group, an arlyoxy group, an ether group, a sulfide group, a disulfide group, a silyl group, a germyl group, a stannyl group, a phosphino group, a boryl group, a halogen atom and a hydrogen atom. 
 
     
     
         2 . An organic semiconductor material according to  claim 1 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9  and R 10  is at least one kind of substituent selected from the group consisting of: an aliphatic hydrocarbon group having a substituent and of which number of carbon atoms ranges from 1 to 20, an aromatic hydrocarbon group having a substituent, a complex aromatic group, a carboxyl group, a hydride, an ester group, a cyano group, a hydroxyl group, a halogen atom and a hydrogen atom. 
     
     
         3 . An organic semiconductor material according to  claim 2 , wherein a substituent at a part of acene bone is an alkyl group having greater than 3 carbon atoms. 
     
     
         4 . An organic semiconductor material consisting of a polyacene derivative expressed by the following general formula (2): 
       
         
           
           
               
               
           
         
       
       wherein n is an integer ranging of from 0 to 20;
 wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  may be independently the same substituents or different substituents, when n is greater than 2, a plurality of R 5  existing the general formula (2) may be the same substituents or different substituents, a plurality of R 8  existing in the general formula (2) may be the same substituents or different substituents and R 1 , R 4 , R 5  and R 8  may never be hydrogen atoms at the same time; and 
 wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  in the (condition-B1) is at least one kind of substituent selected from the group consisting of an aliphatic hydrocarbon group having a substituent and of which number of carbon atoms ranges from 1 to 20, an aromatic hydrocarbon group having a substituent, a complex aromatic group having a substituent, a carboxyl group, a hydride, an ester group, a cyano group, a hydroxyl group, a thiocarboxyl group, a dithiocarboxyl group, a sulfonic acid group, a sulfinic acid group, a sulfenic acid group, a sulfonyl group, a sulfinyl group, an acyl halide group, a carbamoyl group, a hydrazide group, an imide group, an amide group, an amidino group, an isocyano group, a cyanic acid ester group, an isocyanic acid ester group, a thiocyanic acid ester group, an isothiocyanic acid ester group, a formyl group, a thioformyl group, an acyl group, a thiol group, an amino group, an imino group, a hydrazino group, an alkoxy group, an arlyoxy group, an ether group, a sulfide group, a disulfide group, a silyl group, a germyl group, a stannyl group, a phosphino group, a boryl group, a halogen atom and a hydrogen atom. 
 
     
     
         5 . An organic semiconductor material according to  claim 4 , wherein each of R 1r  R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  is at least one kind of substituent selected from the group consisting of an aliphatic hydrocarbon group having a substituent and of which number of carbon atoms ranges from 1 to 20, an aromatic hydrocarbon group having a substituent, a complex aromatic group having a substituent, a carboxyl group, a hydride, an ester group, a cyano group, a hydroxyl group, a halogen atom and a hydrogen atom. 
     
     
         6 . An organic semiconductor material according to  claim 5 , wherein n is greater than 5 and a substituent at a part of an acene bone is an alkyl group having greater than 3 carbon atoms. 
     
     
         7 . An organic semiconductor material consisting of a polyacene derivative expressed by the following general formula (3): 
       
         
           
           
               
               
           
         
       
       wherein each of R 1 , R 2 , R 3 , R 4 , R 5  and R 6  may be independently the same substituents or different substituents but all of R 1 , R 4 , R 5  and R 6  may never be hydrogen atoms at the same time; and
 wherein each of R 1 , R 2 , R 3 , R 4 , R 5  and R 6  is at least one kind of substituent selected from the group consisting of an aliphatic hydrocarbon group having a substituent and of which number of carbon atoms ranges from 1 to 20, an aromatic hydrocarbon group having a substituent, a complex aromatic group having a substituent, a carboxyl group, a hydride, an ester group, a cyano group, a hydroxyl group, a thiocarboxyl group, a dithiocarboxyl group, a sulfonic acid group, a sulfinic acid group, a sulfenic acid group, a sulfonyl group, a sulfinyl group, an acyl halide group, a carbamoyl group, a hydrazide group, an imide group, an amide group, an amidino group, an isocyano group, a cyanic acid ester group, an isocyanic acid ester group, a thiocyanic acid ester group, an isothiocyanic acid ester group, a formyl group, a thioformyl group, an acyl group, a thiol group, an amino group, an imino group, a hydrazino group, an alkoxy group, an arlyoxy group, an ether group, a sulfide group, a disulfide group, a silyl group, a germyl group, a stannyl group, a phosphino group, a boryl group, a halogen atom and a hydrogen atom. 
 
     
     
         8 . An organic semiconductor thin film made of an organic semiconductor material according to  claim 1 , said organic semiconductor thin film having crystallinity. 
     
     
         9 . An organic semiconductor thin film according to  claim 8 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl group of which number of carbon atoms is greater than 3. 
     
     
         10 . An organic semiconductor thin film according to  claim 9 , having a stack structure. 
     
     
         11 . An organic semiconductor thin film made of an organic semiconductor material according to  claim 2 , said organic semiconductor thin film having crystallinity. 
     
     
         12 . An organic semiconductor thin film according to  claim 11 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl group of which number of carbon atoms is greater than 3. 
     
     
         13 . An organic semiconductor thin film according to  claim 12 , having a stack structure. 
     
     
         14 . An organic semiconductor thin film made of an organic semiconductor material according to  claim 4 , said organic semiconductor thin film having crystallinity. 
     
     
         15 . An organic semiconductor thin film according to  claim 14 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl group having greater than 3 carbon atoms. 
     
     
         16 . An organic semiconductor thin film according to  claim 15 , having a stack structure. 
     
     
         17 . An organic semiconductor thin film made of an organic semiconductor material according to  claim 5 , said organic semiconductor thin film having crystallinity. 
     
     
         18 . An organic semiconductor thin film according to  claim 17 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl group of which number of carbon atoms is greater than 3. 
     
     
         19 . An organic semiconductor thin film according to  claim 18 , having a stack structure. 
     
     
         20 . An organic semiconductor thin film made of an organic semiconductor material according to  claim 7 , said organic semiconductor thin film having crystallinity. 
     
     
         21 . An organic semiconductor device including an organic semiconductor thin film made of the organic semiconductor material according to  claim 1 , said organic semiconductor thin film having crystallinity. 
     
     
         22 . An organic semiconductor device according to  claim 21 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl group having greater than 3 carbon atoms. 
     
     
         23 . An organic semiconductor device according to  claim 22 , wherein the organic semiconductor thin film has a stack structure. 
     
     
         24 . An organic semiconductor device including an organic semiconductor thin film made of the organic semiconductor material according to  claim 2 , said organic semiconductor thin film having crystallinity. 
     
     
         25 . An organic semiconductor device according to  claim 24 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl group having greater than 3 carbon atoms. 
     
     
         26 . An organic semiconductor device according to  claim 25 , wherein the organic semiconductor thin film has a stack structure. 
     
     
         27 . An organic semiconductor device according to  claim 21 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         28 . An organic semiconductor device according to  claim 22 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         29 . An organic semiconductor device according to  claim 23 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         30 . An organic semiconductor device according to  claim 24 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         31 . An organic semiconductor device according to  claim 25 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         32 . An organic semiconductor device according to  claim 26 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         33 . An organic semiconductor device including an organic semiconductor thin film made of an organic semiconductor material according to  claim 4 , said organic semiconductor thin film having crystallinity. 
     
     
         34 . An organic semiconductor device according to  claim 33 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl having greater than 3 carbon atoms. 
     
     
         35 . An organic semiconductor device according to  claim 34 , wherein said organic semiconductor thin film has a stack structure. 
     
     
         36 . An organic semiconductor device including an organic semiconductor thin film made of an organic semiconductor material according to  claim 5 , said organic semiconductor thin film having crystallinity. 
     
     
         37 . An organic semiconductor device according to  claim 36 , wherein a substituent at a part of an acene bone in the organic semiconductor material is an alkyl having greater than 3 carbon atoms. 
     
     
         38 . An organic semiconductor device according to  claim 37 , wherein said organic semiconductor thin film has a stack structure. 
     
     
         39 . An organic semiconductor device according to  claim 33 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         40 . An organic semiconductor device according to  claim 34 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         41 . An organic semiconductor device according to  claim 35 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         42 . An organic semiconductor device according to  claim 36 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         43 . An organic semiconductor device according to  claim 37 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         44 . An organic semiconductor device according to  claim 38 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film. 
     
     
         45 . An organic semiconductor device including an organic semiconductor thin film made of the organic semiconductor material according to  claim 7 , said organic semiconductor thin film having crystallinity. 
     
     
         46 . An organic semiconductor device according to  claim 45 , wherein said organic semiconductor device comprises a source/drain electrode, a channel forming region sandwiched between a source/drain electrode and a source/drain electrode, a gate insulating layer and a gate electrode opposed to said channel forming region through said gate insulating layer, said channel forming region being composed of the organic semiconductor thin film.