Photoelectric Conversion Devices

Abstract

Materials for photoelectric conversion devices, consisting of polyacene derivatives represented by general formula (I) below; and photoelectric conversion devices made by using the materials. The materials for photoelectric conversion devices have excellent workability and productivity, exhibit low toxicity, are easily flexibilized, and have high photoelectric conversion efficiencies. In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A 1 , A 2 , A 3 , and A 4 are independent from each other, either the same or different, and each represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, or the like. n is an integer of 1 or more.

1 - 8 . (canceled) 
     
     
         9 . A photoelectric conversion device comprising, between two electrodes at least one of which is light-transmitting, a layer containing one or more kind of the material for photoelectric conversion devices, wherein the material is composed a polyacene derivative represented by general formula (I) below: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are independent from each other, either the same or different, and each represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted alkoxy group having 1 to 40 carbon atoms, an optionally substituted aryloxy group having 6 to 40 carbon atoms, an optionally substituted amino group, a hydroxyl group, or an optionally substituted silyl group;
 A 1 , A 2 , A 3 , and A 4  are independent from each other, either the same or different, and each represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted alkoxy group having 1 to 40 carbon atoms, an optionally substituted aryloxy group having 6 to 40 carbon atoms, an optionally substituted alkylaryloxy group having 7 to 40 carbon atoms, an optionally substituted alkoxycarbonyl group having 2 to 40 carbon atoms, an optionally substituted aryloxycarbonyl group having 7 to 40 carbon atoms, a cyano group  ˜ (CN), a carbamoyl group  ˜ (C(═O)NH 2 ), a haloformyl group  ˜ (C(═O) ˜ X, wherein X represents a halogen atom), a formyl group  ˜ (C(═O) ˜ H), an isocyano group, an isocyanato group, a thiocyanato group, or a thioisocyanato group; or for each of the pair A 1  and A 2  and the pair A 3  and A 4 , the groups may link to each other to form a ring represented by  ˜ C(═O) ˜ B ˜ C(═O) ˜ , wherein B is an oxygen atom or a group represented by  ˜ N(B 1 ) ˜ , B 1  being a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms or a halogen atom; and A 3  and A 4  may link to each other to form a saturated or unsaturated ring having 4 to 40 carbon atoms, the saturated or unsaturated ring being optionally interrupted by an oxygen atom, a sulfur atom, or a group represented by  ˜ N(R 11 ) ˜ , wherein R 11  is a hydrogen atom or a hydrocarbon group, the saturated or unsaturated ring optionally having a substituent(s); and 
 n is an integer of 1 or more. 
 
     
     
         10 . A photoelectric conversion device comprising a layer containing an organic semiconductor disposed between two electrodes at least one of which is light-transmitting, wherein the layer containing the organic semiconductor contains one or more kinds of the material for photoelectric conversion devices, the material being composed of the polyacene derivative represented by general formula (I) described in  claim 9 . 
     
     
         11 . A photoelectric conversion device which performs photoelectric conversion comprising a layer containing semiconductor fine particles on which a pigment is absorbed and a p-type organic semiconductor working as a hole-transporting layer disposed between two electrodes at least one of which is light-transmitting, wherein the hole-transporting layer contains one or more kinds of the material for photoelectric conversion devices, the material being composed of the polyacene derivative represented by general formula (I) described in  claim 9 . 
     
     
         12 . A photoelectric conversion device comprising a semiconductor layer(s) disposed between two electrodes at least one of which is light-transmitting, which performs photoelectric conversion based on an organic semiconductor/metal junction, an organic semiconductor/inorganic semiconductor junction, or an organic semiconductor/organic semiconductor junction, wherein the organic semiconductor layer contains one or more kinds of the material for photoelectric conversion devices, the material being composed of the polyacene derivative represented by general formula (I) described in  claim 9 . 
     
     
         13 . The photoelectric conversion devices according to  claim 9 , wherein the polyacene derivative represented by general formula (I) is a polyacene derivative in which at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A 1 , A 2 , A 3 , and A 4  is not a hydrogen atom. 
     
     
         14 . The photoelectric conversion device according to  claim 9 , wherein the polyacene derivative represented by general formula (I) is a p-type organic semiconductor. 
     
     
         15 . The photoelectric conversion device according to  claim 9 , wherein the polyacene derivative represented by general formula (I) is an n-type organic semiconductor. 
     
     
         16 . The photoelectric conversion devices according to  claim 10 , wherein the polyacene derivative represented by general formula (I) is a polyacene derivative in which at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A 1 , A 2 , A 3 , and A 4  is not a hydrogen atom. 
     
     
         17 . The photoelectric conversion devices according to  claim 11 , wherein the polyacene derivative represented by general formula (I) is a polyacene derivative in which at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A 1 , A 2 , A 3 , and A 4  is not a hydrogen atom. 
     
     
         18 . The photoelectric conversion devices according to  claim 12 , wherein the polyacene derivative represented by general formula (I) is a polyacene derivative in which at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A 1 , A 2 , A 3 , and A 4  is not a hydrogen atom. 
     
     
         19 . The photoelectric conversion device according to  claim 10 , wherein the polyacene derivative represented by general formula (I) is a p-type organic semiconductor. 
     
     
         20 . The photoelectric conversion device according to  claim 11 , wherein the polyacene derivative represented by general formula (I) is a p-type organic semiconductor. 
     
     
         21 . The photoelectric conversion device according to  claim 12 , wherein the polyacene derivative represented by general formula (I) is a p-type organic semiconductor. 
     
     
         22 . The photoelectric conversion device according to  claim 10 , wherein the polyacene derivative represented by general formula (I) is an n-type organic semiconductor. 
     
     
         23 . The photoelectric conversion device according to  claim 11 , wherein the polyacene derivative represented by general formula (I) is an n-type organic semiconductor. 
     
     
         24 . The photoelectric conversion device according to  claim 12 , wherein the polyacene derivative represented by general formula (I) is an n-type organic semiconductor.