Photoelectric conversion film, photoelectric conversion element and electronic device

Patent metadata

Field	Value
Publication number	US-10672994-B2
Application number	US-201515308174-A
Country	US
Kind code	B2
Filing date	Apr 8, 2015
Priority date	May 13, 2014
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

There is provided a photoelectric conversion film including a quinacridone derivative represented by the following General formula (1) and a subphthalocyanine derivative represented by the following General formula (2).

First claim

What is claimed is:

1. A photoelectric conversion film comprising:
a quinacridone derivative represented by General formula (1):

and
a subphthalocyanine derivative represented by General formula (2):

wherein the quinacridone derivative and the subphthalocyanine derivative form a bulk hetero mixed film,
wherein at least one of the quinacridone derivative and the subphthalocyanine derivative forming the bulk hetero mixed film is in a crystalline state,
wherein in General formula (1), R 1 to R 10 are each independently selected from the group consisting of hydrogen, a halogen, a hydroxy group, an alkoxy group, a cyano group, a nitro group, a silylalkyl group, a silylalkoxy group, an arylsilyl group, a thioalkyl group, a thioaryl group, a sulfonyl group, an arylsulfonyl group, an alkylsulfonyl group, an amino group, an alkylamino group, an arylamino group, an acyl group, an acylamino group, an acyloxy group, a carboxy group, a carboxamido group, a carboalkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and an aryl or heteroaryl group formed by condensing at least two of the R 1 to R 10 that are adjacent to one another,
wherein in General formula (2), R 11 to R 16 are each independently selected from the group consisting of hydrogen, a halogen, a hydroxy group, an alkoxy group, a cyano group, a nitro group, a silylalkyl group, a silylalkoxy group, an arylsilyl group, a thioalkyl group, a thioaryl group, a sulfonyl group, an arylsulfonyl group, an alkylsulfonyl group, an amino group, an alkylamino group, an arylamino group, an acyl group, an acylamino group, an acyloxy group, a carboxy group, a carboxamido group, a carboalkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group,
wherein X is selected from the group consisting of a halogen, a hydroxy group, a thiol group, an imide group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkylthio group, and a substituted or unsubstituted arylthio group, and
wherein at least one of R 11 to R 16 represents fluorine.

2. The photoelectric conversion film according to claim 1 , wherein both of the quinacridone derivative and the subphthalocyanine derivative forming the bulk hetero mixed film are in a crystalline state.

3. The photoelectric conversion film according to claim 1 , wherein the bulk hetero mixed film has a microstructure in which an amorphous layer uniformly covers a surface of crystal fine particles.

4. The photoelectric conversion film according to claim 1 , wherein the other of the quinacridone derivative and the subphthalocyanine derivative forming the bulk hetero mixed film is in an amorphous state.

5. The photoelectric conversion film according to claim 1 , wherein R 11 to R 16 are each fluorine.

6. The photoelectric conversion film according to claim 1 , wherein X is selected from the group consisting of a halogen, a hydroxy group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy group.

7. The photoelectric conversion film according to claim 1 , wherein a lowest unoccupied molecular orbital (LUMO) level of the subphthalocyanine derivative is deeper than a LUMO level of the quinacridone derivative, and a difference between the LUMO level of the subphthalocyanine derivative and the LUMO level of the quinacridone derivative is greater than or equal to 0.1 eV and less than or equal to 1.0 eV.

8. A photoelectric conversion film comprising:
a transparent compound that does not absorb visible light and that is represented by at least one of General formula (3) and General formula (4):

and
an organic dye compound;
wherein the transparent compound and the organic dye compound form a bulk hetero mixed film,
wherein at least one of the transparent compound and the organic dye compound forming the bulk hetero mixed film is in a crystalline state,
wherein in General formula (3), R 21 to R 32 are each independently selected from the group consisting of hydrogen, a halogen, a hydroxy group, an alkoxy group, a cyano group, a nitro group, a silylalkyl group, a silylalkoxy group, an arylsilyl group, a thioalkyl group, a thioaryl group, a sulfonyl group, an arylsulfonyl group, an alkylsulfonyl group, an amino group, an alkylamino group, an arylamino group, an acyl group, an acylamino group, an acyloxy group, a carboxy group, a carboxamido group, a carboalkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and an aryl or heteroaryl group formed by condensing at least two of the R 21 to R 32 that are adjacent to one another, and
wherein in General formula (4), R 41 to R 48 are each independently selected from the group consisting of hydrogen, a halogen, a hydroxy group, an alkoxy group, a cyano group, a nitro group, a silylalkyl group, a silylalkoxy group, an arylsilyl group, a thioalkyl group, a thioaryl group, a sulfonyl group, an arylsulfonyl group, an alkylsulfonyl group, an amino group, an alkylamino group, an arylamino group, an acyl group, an acylamino group, an acyloxy group, an imide group, a carboxy group, a carboxamido group, a carboalkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and an aryl or heteroaryl group formed by condensing at least two of the R 41 to R 48 that are adjacent to one another, and
wherein Ar 1 to Ar 4 are each independently one of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group.

9. The photoelectric conversion film according to claim 8 , wherein both of the transparent compound and the organic dye compound forming the bulk hetero mixed film are in a crystalline state.

10. The photoelectric conversion film according to claim 8 , wherein the bulk hetero mixed film has a microstructure in which an amorphous layer uniformly covers a surface of crystal fine particles.

11. The photoelectric conversion film according to claim 8 , wherein the other of the transparent compound and the organic dye compound forming the bulk hetero mixed film is in an amorphous state.

12. The photoelectric conversion film according to claim 8 , wherein the transparent compound is represented by at least General formula (3) and R 21 , R 24 , R 25 , R 28 , R 29 , and R 32 are each hydrogen in General formula (3).

13. The photoelectric conversion film according to claim 8 , wherein the transparent compound is represented by at least General formula (4) and at least one of Ar 1 to Ar 4 and R 41 to R 48 is an electron attracting group in General formula (4).

14. The photoelectric conversion film according to claim 13 , wherein the electron attracting group is selected from the

Assignees

• Sony Semiconductor Solutions Corp

Inventors

• Obana Yoshiaki
• Negishi Yuki
• Hasegawa Yuta
• Takemura Ichiro
• Enoki Osamu
• Mogi Hideaki
• Matsuzawa Nobuyuki

Classifications

• H01L51/4246

  Electricity · mapped topic

• H01L51/424

  Electricity · mapped topic

• Y02E10/549

  Organic PV cells · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C09B67/0033

  Blends of pigments; Mixtured crystals; Solid solutions · CPC title