IP Library Granted Patent US 9,634,261
Granted Patent B2
US 9,634,261 · App. 13/805,832 · Granted Apr 25, 2017

Organic photoelectric conversion element and solar cell using same

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Quick Facts
Patent No.
US 9,634,261
App. No.
13/805,832
Granted
Apr 25, 2017
Kind
B2
Abstract

Disclosed is an organic photoelectric conversion element which has a reverse layer structure wherein at least a first electrode, a photoelectric conversion layer and a second electrode are arranged on a substrate in this order. The organic photoelectric conversion element is characterized in that: the photoelectric conversion layer is a bulk heterojunction layer that is composed of a p-type organic semiconductor material and an n-type organic semiconductor material; and a compound that has a linear or branched fluorinated alkyl group having 6-20 carbon atoms is contained as the p-type organic semiconductor material.

Claims (59)

1. An organic photoelectric conversion element having a reverse layer structure comprising a substrate having thereon at least a first electrode, a photoelectric conversion layer and a second electrode in this order,

wherein the photoelectric conversion layer is a bulk heterojunction layer comprising a p-type organic semiconductor material and a n-type organic semiconductor material, and the p-type organic semiconductor material comprises a compound that has a linear or branched fluorinated alkyl group having 6 to 20 carbon atoms; and

the fluorinated alkyl group is represented by Formula (1)

wherein p, q, r, s=0 to 20, m=1 to 3, n=0 to 2, 2≦m+n≦3, and p, q, r, s, m and n each represent an integer.

2. The organic photoelectric conversion element of claim 1 , wherein the fluorinated alkyl group has 8 to 20 carbon atoms.

3. The organic photoelectric conversion element of claim 1 , wherein Formula (1) meets m≧1 and n≧1.

4. The organic photoelectric conversion element of claim 1 , wherein the compound having the fluorinated alkyl group has a substructure represented by Formula (2):

wherein Rf represents the linear or branched fluorinated alkyl group having 6 to 20 carbon atoms, X represents an atom selected from CH and N, and L represents a single bond or a divalent connecting group.

5. The organic photoelectric conversion element of claim 4 , wherein, in Formula (2), L represents a carbonyl group, an ester group or an amide group.

6. The organic photoelectric conversion element of claim 4 wherein, in Formula (2), L represents an ester group.

7. The organic photoelectric conversion element of claim 1 , wherein at least one fluorinated alkyl group has 7 to 17 fluorine atoms.

8. The organic photoelectric conversion element of claim 1 , wherein the compound having the fluorinated alkyl group is a copolymer of a monomer having the fluorinated alkyl group and a monomer having a common mother moiety with the monomer having the fluorinated alkyl group and having no fluorinated alkyl group.

9. The organic photoelectric conversion element of claim 1 , wherein the bulk heterojunction layer is formed via a wet process.

10. A solar cell comprising the organic photoelectric conversion element of claim 1 .

11. An organic photoelectric conversion element having a reverse layer structure comprising a substrate having thereon at least a first electrode, a photoelectric conversion layer and a second electrode in this order,

wherein the photoelectric conversion layer is a bulk heterojunction layer comprising a p-type organic semiconductor material and an n-type organic semiconductor material, and

the p-type organic semiconductor material comprises a compound that has a linear or branched fluorinated alkyl group having 8 to 20 carbon atoms; and

the fluorinated alkyl group is represented by Formula (1)

wherein p, q, r, s=0 to 20, m=1 to 3, n=0 to 2, and p, q, r and s each represent an integer;

the p-type organic semiconductor material is composed of a mixture of:

the p-type organic semiconductor compound having the fluorinated alkyl group,

and a p-type organic semiconductor compound without a fluorinated alkyl group,

provided that a ratio of the two compounds is between 1:99 to 30:70; and

wherein Formula (1) meets 3≧m+n≧2.

12. The organic photoelectric conversion element of claim 11 , wherein at least one fluorinated alkyl group has 7 to 17 fluorine atoms.

13. The organic photoelectric conversion element of claim 11 , wherein the compound having the fluorinated alkyl group is a copolymer of a monomer having the fluorinated alkyl group and a monomer having a common mother moiety with the monomer having the fluorinated alkyl group and having no fluorinated alkyl group.

14. The organic photoelectric conversion element of claim 11 , wherein the bulk heterojunction layer is formed via a wet process.

15. A solar cell comprising the organic photoelectric conversion element of claim 11 .

16. An organic photoelectric conversion element having a reverse layer structure comprising a substrate having thereon at least a first electrode, a photoelectric conversion layer and a second electrode in this order,

wherein the photoelectric conversion layer is a bulk heterojunction layer comprising a p-type organic semiconductor material and an n-type organic semiconductor material, and

the p-type organic semiconductor material comprises a compound that has a linear or branched fluorinated alkyl group having 8 to 20 carbon atoms; and

the fluorinated alkyl group is represented by Formula (1)

wherein p, q, r, s=0 to 20, m=1 to 3, n=0 to 2, 1≦m+n≦3, and p, q, r and s each represent an integer;

the p-type organic semiconductor material is composed of a mixture of:

the p-type organic semiconductor compound having the fluorinated alkyl group,

and a p-type organic semiconductor compound without a fluorinated alkyl group,

provided that a ratio of the two compounds is between 1:99 to 30:70; and

wherein Formula (1) meets m≧1 and n≧1.

17. The organic photoelectric conversion element of claim 16 , wherein at least one fluorinated alkyl group has 7 to 17 fluorine atoms.

18. The organic photoelectric conversion element of claim 16 , wherein the compound having the fluorinated alkyl group is a copolymer of a monomer having the fluorinated alkyl group and a monomer having a common mother moiety with the monomer having the fluorinated alkyl group and having no fluorinated alkyl group.

19. The organic photoelectric conversion element of claim 16 , wherein the bulk heterojunction layer is formed via a wet process.

20. A solar cell comprising the organic photoelectric conversion element of claim 16 .

21. An organic photoelectric conversion element having a reverse layer structure comprising a substrate having thereon at least a first electrode, a photoelectric conversion layer and a second electrode in this order,

wherein the photoelectric conversion layer is a bulk heterojunction layer comprising a p-type organic semiconductor material and an n-type organic semiconductor material, and

the p-type organic semiconductor material comprises a compound that has a linear or branched fluorinated alkyl group having 8 to 20 carbon atoms; and

the fluorinated alkyl group is represented by Formula (1)

wherein p, q, r, s=0 to 20, m=1 to 3, n=0 to 2, 1≦m+n≦3, and p, q, r and s each represent an integer;

the p-type organic semiconductor material is composed of a mixture of:

the p-type organic semiconductor compound having the fluorinated alkyl group,

and a p-type organic semiconductor compound without a fluorinated alkyl group,

provided that a ratio of the two compounds is between 1:99 to 30:70; and

wherein the compound having the fluorinated alkyl group has a substructure represented by Formula (2):

wherein Rf represents the linear or branched fluorinated alkyl group having 6 to 20 carbon atoms, X represents an atom selected from CH and N, and L represents a single bond or a divalent connecting group.

22. The organic photoelectric conversion element of claim 21 , wherein in Formula (2), L represents a carbonyl group, an ester group or an amide group.

23. The organic photoelectric conversion element of claim 21 , wherein in Formula (2), L represents an ester group.

24. The organic photoelectric conversion element of claim 21 , wherein at least one fluorinated alkyl group has 7 to 17 fluorine atoms.

25. The organic photoelectric conversion element of claim 21 , wherein the compound having the fluorinated alkyl group is a copolymer of a monomer having the fluorinated alkyl group and a monomer having a common mother moiety with the monomer having the fluorinated alkyl group and having no fluorinated alkyl group.

26. The organic photoelectric conversion element of claim 21 , wherein the bulk heterojunction layer is formed via a wet process.

27. A solar cell comprising the organic photoelectric conversion element of claim 21 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2020
From: KONICA MINOLTA, INC.
To: SONY SEMICONDUCTOR SOLUTIONS CORPORATION
Reel/Frame 051922/0959 →
MERGER Recorded Mar 10, 2017
From: KONICA MINOLTA HOLDINGS, INC.
To: KONICA MINOLTA, INC.
Reel/Frame 041540/0922 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 20, 2012
From: OKUBO, YASUSHI; TANI, KUNIO
To: KONICA MINOLTA HOLDINGS, INC.
Reel/Frame 029509/0775 →