Organic compound, photovoltaic layer and organic photovoltaic device

Abstract

The present invention relates generally to the field of organic chemistry and particularly to the organic compound for organic photovoltaic devices. More specifically, the present invention is related to the organic compounds and the organic photovoltaic devices based on these compounds. In one preferred embodiment, this organic compound has the general structural formula where Het 1 is a predominantly planar polycyclic molecular system of first type; Het 2 is a predominantly planar polycyclic molecular system of second type; A is a bridging group providing a lateral bond of the molecular system Het 1 with the molecular system Het 2 via strong chemical bonds; n is 1, 2, 3, 4, 5, 6, 7 or 8; B1 and B2 are binding groups; i is 0, 1, 2, 3, 4, 5, 6, 7 or 8; j is 0, 1, 2, 3, 4, 5, 6, 7 or 8; S1 and S2 are groups providing solubility of the organic compound; k is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m is 0, 1, 2, 3, 4, 5, 6, 7 or 8; D1 and D2 are substituents independently selected from a list comprising —CH 3 , —C 2 H 5 , —NO 2 , —Cl, —Br, —F, —CF 3 , —CN, —OH, —OCH 3 , —OC 2 H 5 , —OCOCH 3 , —OCN, —SCN—NH 2 , —NHCOCH 3 , —C 2 Si(CH 3 ) 3 , and —CONH 2 ; y is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and z is 0, 1, 2, 3, 4, 5, 6, 7 or 8. Said organic compound absorbs electromagnetic radiation in at least one predetermined spectral subrange within a wavelength range from 400 to 3000 nm and is capable to form supramolecules. The molecular system Het 1 , the bridging group A, and the molecular system Het 2 are capable to form a donor-bridge-acceptor system providing dissociation of excited electron-hole pairs. A solution of the organic compound or its salt is capable of forming a solid photovoltaic layer on a substrate.

1 - 20 . (canceled) 
     
     
         21 . An organic photovoltaic device comprising a first and a second electrode and at least one solid organic photovoltaic layer, wherein said layer comprises at least one organic compound having the general structural formula II: 
       
         
           
           
               
               
           
         
         where Het 1  is a predominantly planar polycyclic molecular system of a first type;
 Het 2  is a predominantly planar polycyclic molecular system of a second type; 
 A is a bridging group providing a lateral bond of the molecular system Het 1  with the molecular system Het 2  via strong chemical bonds; 
 n is 2, 3, 4, 5, 6, 7 or 8; 
 B1 and B2 are binding groups; 
 i is 0, 1, 2, 3, 4, 5, 6, 7 or 8; 
 j is 0, 1, 2, 3, 4, 5, 6, 7 or 8; 
 S1 and S2 are groups providing solubility of the at least one organic compound; 
 k is 0, 1, 2, 3, 4, 5, 6, 7 or 8; 
 m is 0, 1, 2, 3, 4, 5, 6, 7 or 8; 
 wherein k+m≠0, 
 D1 and D2 are substituents independently selected from a list consisting of —CH 3 , —C 2 H 5 , —C 3 H 7 , —NO 2 , —Cl, —Br, —F, —CF 3 , —CN, —OH, —OCH 3 , —OC 2 H 5 , —OCOCH 3 , —OCN, —SCN, —NH 2 , —NHCOCH 3 , —C 2 Si(CH 3 ) 3 , and —CONH 2 ; and 
 y is 0, 1, 2, 3, 4, 5, 6, 7 or 8; 
 z is 0, 1, 2, 3, 4, 5, 6, 7 or 8; 
 X is a counterion selected from a list consisting of H + , Li + , Na + , K + , NH 4   + , Ba ++ , Zn ++ , Sr ++ , Ca ++ , Mg ++ , and any combination thereof; 
 t is the number of counterions providing for the electric neutrality of the at least one organic compound; 
 
         wherein the photovoltaic layer is formed of column-like or planar supramolecules, 
         wherein the photovoltaic layer has absorption of electromagnetic radiation in at least one predetermined spectral subrange within a wavelength range from 400 to 3000 nm, and 
         wherein the molecular system Het 1 , the bridging group A, and the molecular system Het 2  form a donor-bridge-acceptor system providing dissociation of excited electron-hole pairs. 
       
     
     
         22 . The organic photovoltaic device according to  claim 21 , wherein at least one of the predominantly planar polycyclic molecular systems Het 1  and Het 2  is a heterocyclic molecular system. 
     
     
         23 . The organic photovoltaic device according to  claim 21 , wherein the predominantly planar polycyclic molecular system of first type (Het 1 ) and at least one predominantly planar polycyclic molecular system of second type (Het 2 ) absorb electromagnetic radiation in different predetermined spectral subranges within a wavelength range from 400 to 3000 nm. 
     
     
         24 . The organic photovoltaic device according to  claim 21 , wherein the strong chemical bond is selected from the list consisting of covalent bond, coordination bond, ionic bond, and any combination thereof. 
     
     
         25 . The organic photovoltaic device according to  claim 21 , wherein the photovoltaic layer has column-like supramolecules formed by means of π-π-interaction of single-type polycyclic molecular systems and having longitudinal axes oriented predominantly in the layer plane, wherein the column-like supramolecules are positioned predominantly parallel to each other. 
     
     
         26 . The organic photovoltaic device according to claim  5 , wherein a number and a chain length of the substituents are selected to provide an electric isolation of the adjacent column-like supramolecules. 
     
     
         27 . The organic photovoltaic device according to  claim 21 , wherein the photovoltaic layer comprises photovoltaic fibers oriented predominantly parallel to each other in the layer plane. 
     
     
         28 . The organic photovoltaic device according to  claim 21 , comprising at least one woven photovoltaic layer comprising photovoltaic fibers, wherein the photovoltaic fibers are arranged predominantly parallel to each other. 
     
     
         29 . The organic photovoltaic device according to  claim 21 , wherein the photovoltaic layer has planar supramolecules having polycyclic molecular systems with planes oriented predominantly parallel to the layer plane due to lateral interaction of binding groups by means of strong and weak chemical bonds, wherein at least one of said planar supramolecules has the form selected from the list consisting of disk, plate, lamella, ribbon or any combination thereof, and wherein the weak chemical bond is selected from the list consisting of single hydrogen bond, dipole-dipole interaction, cation-π interaction, van der Waals interaction, π-π interaction, and any combination thereof. 
     
     
         30 . The organic photovoltaic device according to  claim 29 , wherein the planar supramolecules form molecular stacks by means of π-π-interaction of the single-type polycyclic molecular systems Het 1  and Het 2  providing different current-conducting-paths with electron and hole conductivity respectively, wherein said molecular stacks are electrically isolated among themselves due to the substituents or/and groups providing solubility of the organic compound, and wherein the molecular stacks are oriented predominantly perpendicular to the plane of the photovoltaic layer. 
     
     
         31 . The organic photovoltaic device according to  claim 21 , wherein the predetermined spectral subrange is from 400 to 700 nm. 
     
     
         32 . The organic photovoltaic device according to  claim 21 , wherein at least one of the predominantly planar polycyclic molecular systems Het 1  and Het 2  is partially or completely conjugated. 
     
     
         33 . The organic photovoltaic device according to claim  2 , wherein at least one of the predominantly planar polycyclic molecular systems Het 1  and Het 2  comprises the hetero-atoms selected from the list consisting of nitrogen, oxygen, sulfur, and any combination thereof. 
     
     
         34 . The organic photovoltaic device according to  claim 21 , wherein at least one of the bridging groups A is independently selected from the list consisting of an imidazole; perylene-3,4-dicarboximide; a series of p-phenylene (Ph P ) oligomers, where p is 1, 2, 3, 4 or 5; and a series of 2,7-oligofluorene (FL S ) oligomers, where s is 1, 2, 3, or 4. 
     
     
         35 . The organic photovoltaic device according to  claim 21 , wherein at least one of the predominantly planar polycyclic molecular systems Het 1  and Het 2  comprises tetrapirolic macrocyclic fragments and having a general structural formula selected from the group consisting of structures 1-6, where M denotes an atom of metal or two protons (2H): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         36 . The organic photovoltaic layer according to  claim 21 , wherein at least one of the predominantly planar polycyclic molecular systems Het 1  and Het 2  comprises rylene fragments and having a general structural formula selected from the group consisting of structures 7-27: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         37 . The organic photovoltaic layer according to  claim 21 , wherein at least one of the predominantly planar polycyclic molecular systems Het 1  and Het 2  comprises naphthalene fragments having a general structural formula selected from the group consisting of structures 28-29: 
       
         
           
           
               
               
           
         
       
     
     
         38 . The organic photovoltaic layer according to  claim 30 , wherein the molecular stacks are oriented predominantly perpendicular to the plane of the photovoltaic layer. 
     
     
         39 . The organic photovoltaic layer according to  claim 25 , comprising the parallel column-like supramolecules oriented predominantly in the plane of the photovoltaic layer. 
     
     
         40 . The organic photovoltaic layer according to  claim 27 , comprising the parallel photovoltaic fibers oriented predominantly in the plane of the photovoltaic layer.