Organic compound and organic photoelectric conversion element including the same

Patent metadata

Field	Value
Publication number	US-10978644-B2
Application number	US-201916243500-A
Country	US
Kind code	B2
Filing date	Jan 9, 2019
Priority date	Jul 21, 2016
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

In General Formula 1, a partial structure Z1 represents a condensed polycyclic group that may include a nitrogen atom in a skeleton, and that includes at least one of a five-membered ring and a six-membered ring. The partial structure Z1 may include, as a substituent, a carbonyl group, a dicyanovinylidene group, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aromatic heterocyclic group, or an aryl group. R1 and R2 represent an alkyl group, aryl group, an aromatic heterocyclic group, a halogen group, or a cyano group. Ar1 represents an arylene group or a divalent aromatic heterocyclic group, and Ar2 and Ar3 represent an aryl group or an aromatic heterocyclic group. n represents an integer of 1 to 4.

First claim

What is claimed is:

1. An organic photoelectric conversion element comprising:
an anode;
a cathode; and
a photoelectric conversion unit disposed between the anode and the cathode,
wherein the photoelectric conversion unit includes an organic compound layer including at least an organic compound expressed by general formula 1:

wherein:
a partial structure Z1 represents a condensed polycyclic group that may include a nitrogen atom in a skeleton, and that includes at least one of a five-membered ring and a six-membered ring, and the partial structure Z1 may include, as a substituent, a carbonyl group, a dicyanovinylidene group, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aromatic heterocyclic group, and/or an aryl group;
R 1 and R 2 represent a hydrogen atom, an alkyl group, aryl group, an aromatic heterocyclic group, a halogen group, or a cyano group, Ar 1 represents a phenylene group, a biphenylene group, or a naphthylene group, and Ar 2 and Ar 3 independently represent any one of a phenyl group, a biphenyl group, and a naphthyl group, and Ar 1 to Ar 3 may include, as a substituent, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aromatic heterocyclic group, and/or an aryl group; and
n represents an integer of 1 to 4.

2. The organic photoelectric conversion element according to claim 1 , wherein the organic compound layer includes an organic n-type semiconductor.

3. The organic photoelectric conversion element according to claim 2 , wherein the organic n-type semiconductor is fullerene or a fullerene derivative.

4. An optical area sensor comprising a plurality of organic photoelectric conversion elements, wherein:
each organic photoelectric conversion element is the organic photoelectric conversion element according to claim 1 ; and
the organic photoelectric conversion elements are arranged two-dimensionally in an in-plane direction.

5. An organic photoelectric conversion apparatus comprising a plurality of organic photoelectric conversion elements that have different reception light wavelengths,
wherein:
at least one organic photoelectric conversion element among the plurality of organic photoelectric conversion elements is the organic photoelectric conversion element according to claim 1 ; and
the plurality of organic photoelectric conversion elements are stacked.

6. An optical area sensor comprising a plurality of photoelectric conversion apparatuses, wherein:
each photoelectric conversion apparatus is the photoelectric conversion apparatus according to claim 5 ; and
the photoelectric conversion apparatuses are arranged two-dimensionally in an in-plane direction.

7. An image pickup element comprising a plurality of organic photoelectric conversion elements, and transistors each connected to each of the organic photoelectric conversion elements, wherein:
the organic photoelectric conversion element is the organic photoelectric conversion element according to claim 1 ; and
each of the organic photoelectric conversion elements is a light receiving pixel.

8. The image pickup element according to claim 7 , comprising an optical filter for the light receiving pixel.

9. The image pickup element according to claim 8 , wherein the optical filter is one of a long pass filter that transmits wavelengths more than or equal to an infrared ray, and a low pass filter that transmits wavelengths of less than or equal to an ultraviolet ray.

10. The image pickup element according to claim 7 , further comprising an optical member disposed in accordance with each of the light receiving pixels.

11. An image pickup apparatus comprising an image pickup optical system, and an image pickup element that receives light having passed the image pickup optical system, wherein the image pickup element is the image pickup element according to claim 7 .

12. The image pickup apparatus according to claim 11 , further comprising a joint unit that can be jointed with the image pickup optical system.

13. The image pickup apparatus according to claim 11 , wherein the image pickup apparatus is a digital camera or a digital still camera.

14. The image pickup apparatus according to claim 11 , further comprising a reception unit that receives a signal from outside, wherein the signal is a signal controlling any of an image pickup range, a start of image pickup, and an end of image pickup.

15. The image pickup apparatus according to claim 11 , further comprising a transmission unit that transmits an obtained image to outside.

16. The organic compound according to claim 1 , wherein the partial structure Z1 may include, as the substituent, a dicyanovinylidene group, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aromatic heterocyclic group, and/or an aryl group.

17. The organic compound according to claim 16 , wherein, in the general formula 1, the partial structure Z1 is a structure expressed by any one of general formulae 11 to 19:

wherein R 21 to R 62 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group.

18. An organic photoelectric conversion element comprising:
an anode;
a cathode; and
a photoelectric conversion unit disposed between the anode and the cathode,
wherein the photoelectric conversion unit includes an organic compound layer including at least an organic compound expressed by general formula 1:

wherein:
a partial structure Z1 represents a condensed polycyclic group that may include a nitrogen atom in a skeleton, and that includes at least one of a five-membered ring and a six-membered ring, and the partial structure Z1 may include, as a substituent, a carbonyl group, a dicyanovinylidene group, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aromatic heterocyclic group, and/or an aryl group;
R 1 and R 2 represent an alkyl group, aryl group, an aromatic heterocyclic group, a halogen group, or a cyano group, Ar 1 represents an arylene group or a divalent aromatic heterocyclic group, and Ar 2 and Ar 3 represent an aryl group or an aromatic heterocyclic group, and Ar 1 to Ar 3 may include, as a substituent, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aromatic heterocyclic group, and/or an aryl group;
n represents an integer of 1 to 4; and
the partial structure Z1 is a structure expressed by any one of general formulae 11 to 19:

wherein R 21 to R 62 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aromatic heterocyclic group, and an aryl group.

19. The organic photoelectric conversion element according to claim 18 , wherein in the general formula 1, Ar 1 represents a phenylene group, a biphenylene group, or a naphthylene group, and Ar 2 and Ar 3 independently represent any one of a phen

Assignees

• Canon Kk

Inventors

• Yamada Naoki
• Kamatani Jun
• Ohrui Hiroki
• Iwawaki Hironobu
• Itabashi Masumi
• Nishide Yosuke
• Miyashita Hirokazu
• Shiobara Satoru
• Yamaguchi Tomona
• Takahashi Tetsuo

Classifications

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D333/20 Primary

  by nitrogen atoms (nitro, nitroso radicals C07D333/12) · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D333/22

  Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom · CPC title