N and P active materials for organic photoelectric conversion layers in organic photodiodes

Patent metadata

Field	Value
Publication number	US-11968895-B2
Application number	US-202016943385-A
Country	US
Kind code	B2
Filing date	Jul 30, 2020
Priority date	Mar 31, 2015
Publication date	Apr 23, 2024
Grant date	Apr 23, 2024

Abstract

The field of the DISCLOSURE lies in active materials for organic image sensors. The present disclosure relates to transparent N materials and/or to transparent P materials and their use in absorption layer(s), photoelectric conversion layer(s) and/or an organic image sensor and methods for their synthesis. The present disclosure also relates to photoelectric conversion layer(s) including an active material according to the present disclosure, to a device, including active material(s) according to the present disclosure or photoelectric conversion layer(s) according to the present disclosure. Moreover, the present disclosure relates to an organic image sensor including photoelectric conversion layer(s) according to the present disclosure.

First claim

The invention claimed is:

1. An organic image sensor, comprising:
a substrate;
a first electrode;
a second electrode; and
an organic photoelectric conversion unit positioned between the first electrode and the second electrode,
wherein the organic photoelectric conversion unit includes a naphthalene dimide based material of formula IIIa,

wherein R is, at each occurrence, independently selected from the group consisting of

—(CF 2 ) 5 CF 3 , —(CH 2 ) 5 CH 3 , —CH 2 —(CF 2 ) 3 —CF 3 ,

2. The organic image sensor according to claim 1 , wherein the naphthalene dimide based material dissociates excitons created on colored N or a mixture of colored N materials (N1:N2) or of another colored P or mixture of colored P and N materials (P2:N or P2:N1:N2) via a process of HOMO dissociation in a P:N heterojunction or P:N bilayer or multilayer junction, where colored refers to an absorption coefficient of more than about 60,000 cm −1 in the visible wavelength range in the region from about 400 nm to about 700 nm.

3. The organic image sensor according to claim 2 , wherein the naphthalene dimide based material has an absorption coefficient of less than about 60,000 cm −1 in the visible wavelength range in the region from about 400 nm to about 700 nm, or an extinction coefficient of less than about 60,000 M −1 cm −1 in toluene, and is forming homogenous films formed by a deposition method.

4. The organic image sensor according to claim 2 , wherein the naphthalene dimide based material is selected from the group consisting of

5. The organic image sensor according to claim 2 , wherein the organic photoelectric conversion unit comprises a photoelectric conversion layer comprising the naphthalene dimide based material and a P material.

6. The organic image sensor according to claim 5 , further comprising:
metal wiring; and
at least one insulating layer,

wherein the substrate is a CMOS substrate.

7. The organic image sensor according to claim 5 , further comprising:
a Si based photoelectric conversion unit;
metal wiring; and
at least one insulating layer,

wherein the substrate is a CMOS substrate.

8. The organic image sensor according to claim 1 , wherein the naphthalene dimide based material has an absorption coefficient of less than about 60,000 cm −1 in the visible wavelength range in the region from about 400 to about 700 nm, or an extinction coefficient of less than about 60,000 M −1 cm −1 in toluene, and is forming homogenous films formed by a deposition method.

9. The organic image sensor according to claim 8 , wherein the naphthalene dimide based material is selected from the group consisting of

10. The organic image sensor according to claim 8 , wherein the organic photoelectric conversion unit comprises a photoelectric conversion layer comprising the naphthalene dimide based material and a P material.

11. The organic image sensor according to claim 10 , further comprising:
metal wiring; and
at least one insulating layer,

wherein the substrate is a CMOS substrate.

12. The organic image sensor according to claim 10 , further comprising:
a Si based photoelectric conversion unit;
metal wiring; and
at least one insulating layer,

wherein the substrate is a CMOS substrate.

13. The organic image sensor according to claim 1 , wherein the naphthalene dimide based material is selected from the group consisting of

14. The organic image sensor according to claim 1 , wherein the organic photoelectric conversion unit comprises a photoelectric conversion layer comprising the naphthalene dimide based material and a P material.

15. The organic image sensor according to claim 14 , further comprising:
metal wiring; and
at least one insulating layer,

wherein the substrate is a CMOS substrate.

16. The organic image sensor according to claim 14 , further comprising:
a Si based photoelectric conversion unit;
metal wiring; and
at least one insulating layer,

wherein the substrate is a CMOS substrate.

17. An organic image sensor, comprising:
a substrate;
a first electrode;
a second electrode; and
an organic photoelectric conversion unit positioned between the first electrode and the second electrode and comprising a photoelectric conversion layer,
wherein the photoelectric conversion layer of the organic photoelectric conversion unit includes a naphthalene dimide based material of formula IIIa,

wherein R is, at each occurrence, independently selected from the group consisting of

—(CF 2 ) 5 CF 3 , —(CH 2 ) 5 CH 3 , —CH 2 —(CF 2 ) 3 —CF 3 ,

18. The organic image sensor according to claim 17 , wherein the naphthalene dimide based material dissociates excitons created on colored N or a mixture of colored N materials (N1:N2) or of another colored P or mixture of colored P and N materials (P2:N or P2:N1:N2) via a process of HOMO dissociation in a P:N heterojunction or P:N bilayer or multilayer junction, where colored refers to an absorption coefficient of more than about 60,000 cm −1 in the visible wavelength range in the region from about 400 nm to about 700 nm.

19. The organic image sensor according to claim 17 , wherein the naphthalene dimide based material has an absorption coefficient of less than about 60,000 cm −1 in the visible wavelength range in the region from about 400 nm to about 700 nm, or an extinction coefficient of less than about 60,000 M −1 cm −1 in toluene, and is forming homogenous films formed by a deposition method.

20. The organic image sensor according to claim 17 , wherein the naphthalene dimide based material is selected from the group consisting of

Assignees

• Sony Corp

Inventors

• Rosselli Silvia
• Danner David
• Miteva Tzenka
• Nelles Gabriele
• Deichmann Vitor
• Ford William E
• Chercka Dennis
• Yakutkin Vladimir
• Scheller Lars Peter
• Knorr Nikolaus

Classifications

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D221/14 Primary

  Aza-phenalenes, e.g. 1,8-naphthalimide · CPC title

• H10F77/122

  comprising only Group IV materials · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D471/06

  Peri-condensed systems · CPC title