Photoelectric conversion film, photoelectric conversion element and electronic device

Patent metadata

Field	Value
Publication number	US-11018308-B2
Application number	US-201916687275-A
Country	US
Kind code	B2
Filing date	Nov 18, 2019
Priority date	May 13, 2014
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

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

First claim

The invention claimed is:

1. A light detecting device, comprising:
a first electrode and a second electrode;
a photoelectric conversion film that selectively absorbs light of a specific wavelength and disposed between the first electrode and the second electrode;
wherein the photoelectric conversion film includes a first compound and a second compound, and the first compound and the second compound are formed as a bulk hetero mixed film,
wherein the first compound is a subphthalocyanine derivative represented by a general formula:

wherein 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, and wherein at least one of R 11 to R 16 is fluorine,
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,
wherein the second compound is configured to transport a hole or an electron,
and
wherein the photoelectric conversion film has a microstructure in which one of the first compound and the second compound is in a crystal fine particle state or in an amorphous state.

2. The light detecting device according to claim 1 , wherein the photoelectric conversion film has a microstructure in which one of the first compound and the second compound is in a crystal fine particle state and the other of the first compound or the second compound is in an amorphous state or a crystal fine particle state.

3. The light detecting device according to claim 1 , wherein the photoelectric conversion film has a microstructure in which the first compound is in a crystal fine particle state and the second compound is in an amorphous state.

4. The light detecting device according to claim 1 , wherein the photoelectric conversion film has a microstructure in which the first compound is in an amorphous state and the second compound is in a crystal fine particle state.

5. The light detecting device according to claim 1 , wherein each of R 11 to R 16 is fluorine.

6. The light detecting device according to claim 1 , wherein at least one of R 11 and R 12 is fluorine, at least one of R 13 and R 14 is fluorine, and at least one of R 15 and R 16 is fluorine.

7. The light detecting device 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.

8. The light detecting according to claim 1 , wherein the first compound is represented by one of the following formulas:

9. The light detecting device according to claim 1 , wherein the first compound is represented by one of the following formulas:

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.

10. The light device according to claim 1 , further comprising a third compound to transport a hole or an electron.

11. The light detecting device according to claim 1 , further comprising a third compound to block a hole from being introduced by the first electrode to the photoelectric conversion film.

12. The light detecting device according to claim 11 , wherein the third compound is an electron accepting material selected from the group consisting of fullerene, carbon nanotubes, oxadiazole, a triazole compound, anthraquinodimethane, diphenylquinone, distyrylarylene, and a silole compound.

13. The light detecting device according to claim 11 , wherein the third compound is fullerene.

14. The light detecting device according to claim 1 , wherein the first compound absorbs green light having a wavelength band of greater than or equal to approximately 450 nm and less than or equal to approximately 600 nm.

15. The light detecting device according to claim 1 , further comprising;
a semiconductor substrate disposed below the photoelectric conversion film,
wherein the semiconductor substrate includes a first photodiode and a second photodiode disposed below the first photodiode, and
wherein the first photodiode absorbs blue light, the second photodiode absorbs red light, and the first photodiode and the second photodiode perform photoelectric conversion.

16. The light detecting device according to claim 1 , further comprising
a semiconductor substrate disposed below the photoelectric conversion film, wherein the semiconductor substrate includes a photoelectric conversion region.

17. The light detecting device according to claim 1 , wherein the first compound has a lowest unoccupied molecular orbital (LUMO) level of greater than or equal to −4.8 eV and less than or equal to −3.5 eV.

18. The light detecting device according to claim 1 , wherein the first compound has a highest occupied molecular orbital (HOMO) level of greater than or equal to −7.0 eV and less than or equal to −5.5 eV.

19. The light detecting device according to claim 1 , wherein a lowest unoccupied molecular orbital (LUMO) level of the first compound is deeper than a LUMO level of the second compound, and a difference between the LUMO level of the first compound and the LUMO level of the second compound is greater than or equal to 0.1 eV and less than or equal to 1.0 eV.

20. The light detecting device according to claim 1 , wherein the light detecting device is a solid-state image sensor.

21. A light detecting device, comprising:
a first electrode;
a second electrode; and
an organic region comprising a first material and a second material, the first material comprises a subphthalocyanine derivative represented by a general formula:

wherein R 11 to R 16 are each 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,

Assignees

• Sony Semiconductor Solutions Corp

Inventors

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

Classifications

• H10K85/311

  Phthalocyanine · CPC title

• C09B47/00 Primary

  Porphines; Azaporphines {(non-dyeing compounds C07D487/22)} · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C09B48/00

  Quinacridones · CPC title