Photoelectric conversion element, image pickup element, laminated image pickup element, and solid-state image pickup device

Abstract

An image pickup element is constituted by laminating at least a first electrode, an organic photoelectric conversion layer, and a second electrode in order, and the organic photoelectric conversion layer includes a first organic semiconductor material having the following structural formula (1).

What is claimed is: 
     
         1 . An image pickup element constituted by laminating at least a first electrode, an organic photoelectric conversion layer, and a second electrode in order, the organic photoelectric conversion layer including a first organic semiconductor material having the following structural formula (1): 
       
         
           
           
               
               
           
         
         where R 1  and R 2  are each groups independently selected from hydrogen, an aromatic hydrocarbon group, a heterocyclic group, a halogenated aromatic group, or a fused heterocyclic group, and have an optional substituent;
 the aromatic hydrocarbon group is an aromatic hydrocarbon group selected from the group consisting of a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, and a benzopyrenyl group; 
 the heterocyclic group is a heterocyclic group selected from the group consisting of a pyridyl group, a pyradyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, a pyrrolyl group, an indolenyl group, an imidazolyl group; a thienyl group, a furyl group, a pyranyl group, and a pyridonyl group; 
 the halogenated aromatic group is a halogenated aromatic group selected from the group consisting of a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, and a benzopyrenyl group; and 
 the fused heterocyclic group is a fused heterocyclic group selected from the group consisting of a benzoquinolyl group, an anthraquinolyl group, and a benzothienyl group. 
 
       
     
     
         2 . An image pickup element constituted by laminating at least a first electrode, an organic photoelectric conversion layer, and a second electrode in order,
 the organic photoelectric conversion layer including a first organic semiconductor material having the following structural formula (2):   
       
         
           
           
               
               
           
         
       
     
     
         3 . The image pickup element according to  claim 1 , wherein the organic photoelectric conversion layer further includes a second organic semiconductor material, the second organic semiconductor material includes either fullerene or a fullerene derivative. 
     
     
         4 . The image pickup element according to  claim 1 , wherein the organic photoelectric conversion layer further includes a second organic semiconductor material and a third organic semiconductor material;
 the second organic semiconductor material includes either fullerene or a fullerene derivative; and   a value μ 3  of a line absorption coefficient in a local maximum optical absorption wavelength of a visible light region of the third organic semiconductor material is larger than a value μ 1  of a line absorption coefficient in a local maximum optical absorption wavelength of a visible light region of the first organic semiconductor material, and is larger than a value μ 2  of a line absorption coefficient in a local maximum optical absorption wavelength of a visible light region of the second organic semiconductor material.   
     
     
         5 . The image pickup element according to  claim 4 , wherein an exciton generated by optical absorption of the third organic semiconductor material is subjected to exciton separation in both interfaces of the organic semiconductor materials selected from two of the first organic semiconductor material, the second organic semiconductor material, and the third organic semiconductor material, or an exciton generated by optical absorption of the third organic semiconductor material is subjected to exciton separation in an interface of one kind of organic semiconductor material selected from the first organic semiconductor material, the second organic semiconductor material, and the third organic semiconductor material. 
     
     
         6 . The image pickup element according to  claim 5 , wherein an exciton charge separation rate at which the exciton is subjected to the exciton separation is 1×10 10  s −1  or more. 
     
     
         7 . The image pickup element according to  claim 4 , wherein the organic photoelectric conversion layer has a local maximum optical absorption wavelength in the range of 450 nm or more to 650 nm or less. 
     
     
         8 . The image pickup element according to  claim 4 , wherein the third organic semiconductor material includes a sub-phthalocyanine system derivative. 
     
     
         9 . The image pickup element according to  claim 4 , wherein the organic photoelectric conversion layer further includes a fourth organic semiconductor material; and
 the fourth organic semiconductor material includes a mother skeleton similar to that of the first organic semiconductor material, or has the same mother skeleton as that of either the second organic semiconductor material or the third organic semiconductor material, and includes a different substituent.   
     
     
         10 . The image pickup element according to  claim 1 , wherein the organic photoelectric conversion layer further includes a second organic semiconductor material and a third organic semiconductor material; and
 an area in a portion in which an energy distribution state density of highest occupied molecular orbital or lowest unoccupied molecular orbital of the second organic semiconductor material, and the an energy distribution state density of highest occupied molecular orbital or lowest unoccupied molecular orbital of the third organic semiconductor material overlap each other is 15 meV or more.   
     
     
         11 . The image pickup element according to  claim 10 , wherein an energy distribution a of the third organic semiconductor material or an energy distribution a of the second organic semiconductor material is 70 meV or less. 
     
     
         12 . The image pickup element according to  claim 1 , wherein hole mobility of the first organic semiconductor material is 1×10 −5  cm 2 /V·s or more. 
     
     
         13 . The image pickup element according to  claim 1 , wherein the first electrode and the second electrode include a transparent conductive material. 
     
     
         14 . The image pickup element according to  claim 1 , wherein one of the first electrode and the second electrode includes a transparent conductive material, and the other includes a metallic material. 
     
     
         15 . A laminated image pickup element constituted by laminating at least two image pickup elements according to  claim 1 . 
     
     
         16 . A solid-state image pickup device comprising a plurality of image pickup elements according to  claim 1 . 
     
     
         17 . A solid-state image pickup device comprising a plurality of laminated image pickup elements according to  claim 15 . 
     
     
         18 . A photoelectric conversion element constituted by laminating at least a first electrode, an organic photoelectric conversion layer, and a second electrode in order, the organic photoelectric conversion layer including a first organic semiconductor material having the following structural formula (1): 
       
         
           
           
               
               
           
         
         where R 1  and R 2  are each groups independently selected from hydrogen, an aromatic hydrocarbon group, a heterocyclic group, a halogenated aromatic group, or a fused heterocyclic group, and have an optional substituent;
 the aromatic hydrocarbon group is an aromatic hydrocarbon group selected from the group consisting of a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, and a benzopyrenyl group; 
 the heterocyclic group is a heterocyclic group selected from the group consisting of a pyridyl group, a pyradyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, a pyrrolyl group, an indolenyl group, an imidazolyl group, a thienyl group, a furyl group, a pyranyl group, and a pyridonyl group; 
 the halogenated aromatic group is a halogenated aromatic group selected from the group consisting of a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, and a benzopyrenyl group; and 
 the fused heterocyclic group is a fused heterocyclic group selected from the group consisting of a benzoquinolyl group, an anthraquinolyl group, and a benzothienyl group. 
 
       
     
     
         19 . A photoelectric conversion element constituted by laminating at least a first electrode, an organic photoelectric conversion layer, and a second electrode in order, the organic photoelectric conversion layer including a first organic semiconductor material having the following structural formula (2): 
       
         
           
           
               
               
           
         
       
     
     
         20 . The photoelectric conversion element according to  claim 18 , wherein the organic photoelectric conversion layer further includes a second organic semiconductor material; and
 the second organic semiconductor material includes either fullerene or a fullerene derivative.   
     
     
         21 . The photoelectric conversion element according to  claim 18 , wherein the organic photoelectric conversion layer further includes a second organic semiconductor material and a third organic semiconductor material;
 the second organic semiconductor material is constituted by either fullerene or a fullerene derivative; and   a value μ 3  of a line absorption coefficient in a local maximum optical absorption wavelength of a visible light region of the third organic semiconductor material is larger than a value μ 1  of a line absorption coefficient in a local maximum optical absorption wavelength of a visible light region of the first organic semiconductor material, and is larger than a value μ 2  of a line absorption coefficient in a local maximum optical absorption wavelength of a visible light region of the second organic semiconductor material.