Organic photoelectric conversion element and solar cell using the same

1. An organic photoelectric conversion element comprising;

a first electrode,

a second electrode, and

a photoelectric conversion layer present between the first electrode and the second electrode, wherein

at least one of the first electrode and the second electrode is a transparent conductive film formed by laminating a ground layer comprising a nitrogen-containing organic compound and a metal thin film layer comprising a metal element of Group 11 of the periodic table and having a thickness of from 2 to 10 nm, and

the nitrogen-containing organic compound comprises a compound represented by the following Formula (1), or a polymer compound having a partial structure represented by the following Formula (2), or a polymer compound having a partial structure represented by the following Formula (3),

(A 1 ) n1 -Y 1   Formula (1)

in Formula (1), A 1 represents a monovalent nitrogen atom-containing group,

n1 represents an integer of 2 or more, and

Y 1 includes a group derived from a structure represented by the following Formula (4)

in Formula (4), Z represents —CR 1 R 2 —, —NR 3 —, —O—, —S—, or —SiR 4 R 5 —,

X 1 to X 8 each independently represent —CR 6 ═ or —N═,

R 1 , R 2 , R 4 , R 5 and R 6 each independently represent a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 1 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms, and

R 3 represents a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from, 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms,

A 2 -Y 2   Formula (2)

in Formula (2), A 2 represents a divalent group derived from a structure formed by two monovalent nitrogen atom-containing groups represented by any of the following structures N-1 to N-11 and N-39 to N-45 which are linked via a divalent linking group selected from the group consisting of a substituted or unsubstituted arylene group having from 6 to 18 carbon atoms, a substituted unsubstituted heteroarylene group having from 6 to 18 carbon atoms and amino group:

and

Y 2 represents a single bond (—),

in Formula (3), A 3 represents a monovalent nitrogen atom-containing group,

A 4 and A 5 each independently represent a divalent nitrogen atom-containing group,

n2 represents an integer of 1 or more,

n3 and n4 each independently represent an integer of 0 or 1, and

Y 3 represents an (n2+2)-valent organic group.

2. The organic photoelectric conversion element according to claim 1 , wherein A 1 or A 3 above comprises a dithiocarbamate group or an amino group.

3. The organic photoelectric conversion element according to claim 1 , wherein A 1 , A 2 , A 3 , A 4 or A 5 above comprises a pyridine ring-containing group.

4. The organic photoelectric conversion element according to claim 1 , wherein Y 3 above includes a group derived from a structure represented by the following Formula (4):

in Formula (4), Z represents —CR 1 R 2 —, —NR 3 —, —O—, —S—, or —SiR 4 R 5 —,

X 1 to X 8 each independently represent —CR 6 ═ or —N═, and

R 1 to R 6 each independently represent a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 1 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms.

5. The organic photoelectric conversion element according to claim 1 , wherein the nitrogen-containing organic compound comprises a compound represented by the Formula (1) and comprising 5 or more nitrogen atoms.

6. The organic photoelectric conversion element according to claim 1 , wherein the metal thin film layer consists of silver.

7. The organic photoelectric conversion element according to claim 1 , wherein the nitrogen compound has a weight average molecular weight of 3,000 or more.

8. The organic photoelectric conversion element according to claim 1 , wherein the ground layer is formed by a manufacturing method comprising a coating process using a solvent comprising a fluorine-containing alcohol.

9. The organic photoelectric conversion element according to claim 1 , wherein the second electrode is the transparent conductive film.

10. The organic photoelectric conversion element according to claim 1 , wherein a thickness of the ground layer is from 5 to 30 nm.

11. The organic photoelectric conversion element according to claim 1 , wherein the transparent conductive film further comprises a protective layer having a refractive index of from 1.5 to 1.8 on the metal thin film layer.

12. A solar cell comprising the organic photoelectric conversion element according to claim 1 .

13. A transparent conductive film comprising a ground layer comprising a nitrogen-containing organic compound and a metal thin film layer formed on the ground layer, the metal thin film layer comprising a transition metal element of Group 11 of the periodic table and having a thickness of from 2 to 10 nm, wherein

the nitrogen-containing organic compound comprises a polymer compound having a partial structure represented by the following Formula (2) or a polymer compound having a partial structure represented by the following Formula (3),

A 2 -Y 2   Formula (2)

in Formula (2), A 2 represents a divalent group derived from a structure formed by two monovalent nitrogen atom-containing groups represented by any of the following structures N-1 to N-11 and N-39 to N-45 which are linked via a divalent linking group selected from the group consisting of a substituted or unsubstituted arylene group having from 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having from 6 to 18 carbon atoms and imino group:

and Y 2 represents a single bond (—),

in Formula (3), A 3 represents a monovalent nitrogen atom-containing group,

A 4 and A 5 each independently represent a divalent nitrogen atom-containing group,

n2 represents an integer of 1 or more,

n3 and n4 each independently represent an integer of 0 or 1, and

Y 3 represents an (n2+2)-valent organic group.

14. A transparent conductive film comprising a ground layer comprising a nitrogen-containing organic compound and a metal thin film layer formed on the ground layer, the metal thin film layer comprising a transition metal element of Group 11 of the periodic table and having a thickness of from 2 to 10 nm, wherein

the nitrogen-containing organic compound comprises a compound comprising 5 or more nitrogen atoms and represented by the following Formula (1):

(A 1 ) n1 -Y 1   Formula (1)

in Formula (1), A 1 represents a monovalent nitrogen atom-containing group,

n1 represents an integer of 2 or more, and

Y 1 includes a group derived from a structure represented by the following Formula (4)

in Formula (4), Z represents —CR 1 R 2 —, —NR 3 —, —O—, —S—, or —SiR 4 R 5 —,

X 1 to X 3 each independently represent —CR 6 ═ or —N═,

R 1 , R 2 , R 4 , R 5 and R 6 each independently represent a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 1 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms, and

R 3 represents a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms.

15. A transparent conductive film comprising a ground layer comprising a nitrogen-containing organic compound and a metal thin film layer formed on the ground layer, the metal thin film layer comprising a transition metal element of Group 11 of the periodic table and having a thickness of from 10 to 30 nm, wherein

the nitrogen-containing organic compound comprises a compound comprising 5 or more nitrogen atoms and represented by the following Formula (1), or a polymer compound having a partial structure represented by the following Formula or a polymer compound having a partial structure represented by the following Formula (3),

(A 1 ) n1 -Y 1   Formula (1)

in Formula (1), A 1 represents a monovalent nitrogen atom-containing group,

n1 represents an integer of 2 or more, and

Y 1 includes a group derived from a structure represented by the following Formula (4)

in Formula (4), Z represents —CR 1 R 2 —, —NR 3 —, —O—, —S—, or —SiR 4 R 5 —,

X 1 to X 8 each independently represent —CR 6 ═ or —N═,

R 1 , R 2 , R 4 , R 5 and R 6 each independently represent a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 1 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms, and

R 3 represents a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms,

A 2 -Y 2   Formula (2)

in Formula (2), A 2 represents a divalent group derived from a structure formed by two monovalent nitrogen atom-containing groups represented by any of the following structures N-1 to N-11 and N-39 to N-45 which are linked via a divalent linking group selected from the group consisting of a substituted or unsubstituted arylene group having from 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having from 6 to 13 carbon atoms and imino group:

and

Y 2 represents a single bond (—),

in Formula (3), A 3 represents a monovalent nitrogen atom-containing group,

A 4 and A 5 each independently represent a divalent nitrogen atom-containing group,

n2 represents an integer of 1 or more,

n3 and n4 each independently represent an integer of 0 or 1, and

Y 3 represents an (n2+2)-valent organic group.

16. A method of manufacturing a transparent conductive film comprising;

forming a ground layer by forming a film of a nitrogen-containing organic compound, and

forming a metal thin film layer comprising a transition metal element of Group 11 of the periodic table and having a thickness of from 2 to 10 nm or from 10 to 30 nm on the ground layer,

wherein the nitrogen-containing organic compound comprises a compound represented by the following Formula (1), or a polymer compound having a partial structure represented by the following Formula (2), or a polymer compound having a partial structure represented by the following Formula (3),

(A 1 ) n1 -Y 1   Formula (1)

in Formula (1), A 1 represents a monovalent nitrogen atom-containing group,

n1 represents an integer of 2 or more, and

Y 1 includes a group derived from a structure represented by the following Formula (4)

in Formula (4), Z represents —CR 1 R 2 —, —NR 3 —, —O—, —S—, or —SiR 4 R 5 —,

X 1 to X 8 each independently represent —CR 6 ═ or —N═,

R 1 , R 2 , R 4 , R 5 and R 6 each independently represent a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 1 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms, and

R 3 represents a single bond (—), a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, or a substituted or unsubstituted alkyloxy group having from 1 to 20 carbon atoms,

A 2 -Y 2   Formula (2)

in Formula (2), A 2 represents a divalent group derived from a structure formed by two monovalent nitrogen atom-containing groups represented by any of the following structures N-1 to N-11 and N-39 to N-45 which are linked via a divalent linking group selected from the group consisting of a substituted or unsubstituted arylene group having from 6 to 18 carbon atoms, a substituted unsubstituted heteroarylene group having from 6 to 18 carbon atoms and imino group:

and

Y 2 represents a single bond (—),

in Formula (3), A 3 represents a monovalent nitrogen atom-containing group,

A 4 and A 5 each independently represent a divalent nitrogen atom-containing group,

n2 represents an integer of 1 or more,

n3 and n4 each independently represent an integer of 0 or 1, and

Y 3 represents an (n2+2)-valent organic group.