Photoelectric conversion element, two-dimensional sensor, image sensor, and image pickup device

Patent metadata

Field	Value
Publication number	US-10947212-B2
Application number	US-201816203298-A
Country	US
Kind code	B2
Filing date	Nov 28, 2018
Priority date	May 31, 2016
Publication date	Mar 16, 2021
Grant date	Mar 16, 2021

Abstract

The present invention provides an organic compound represented by general formula [1] described in claims. In general formula [1], Ar 1 and Ar 2 are each independently selected from an aryl group and a heteroaryl group. In general formula [1], R 1 to R 3 are each a hydrogen atom or a substituent. R 4 is an electron-withdrawing substituent. X 1 is oxygen or sulfur. Y 1 to Y 3 are each independently selected from a carbon atom and a nitrogen atom.

First claim

The invention claimed is:

1. An organic compound represented by general formula [1]:

where in general formula [1], Ar 1 and Ar 2 are each independently selected from the group consisting of an aryl group and a heteroaryl group,
Ar 1 and Ar 2 each optionally have a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group as a substituent, the substituent optionally further has a halogen atom, a cyano group, an alkyl group, or an alkoxy group as a substituent, Ar 1 and Ar 2 are optionally combined with each other to form a ring,
wherein in general formula [1], R 1 and R 2 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, and a hetero aryl group, the alkyl group optionally has a halogen atom as a substituent,
each of the aryl group and the heteroaryl group each denoted by R 1 or R 2 optionally further has a halogen atom, a cyano group, an alkyl group, or an alkoxy group as a substituent, R 1 and R 2 are optionally combined with each other to form a ring,
wherein in general formula [1], R 3 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, and an alkyl group, the alkyl group optionally has a halogen atom as a substituent,
wherein in general formula [1], X 1 is oxygen or sulfur,
wherein in general formula [1], each of Y 1 to Y 3 is a carbon atom or a nitrogen atom, and Y 1 to Y 3 optionally is the same or different,
wherein when at least one of Y 1 to Y 3 is a carbon atom, the carbon atom optionally has a hydrogen atom, a halogen atom, a cyano group, or an alkyl group as a substituent, the alkyl group optionally has a halogen atom as a substituent,
wherein in general formula [1], R 4 is represented by general formula [1-1] or general formula [1-2], each * indicates a bonding position,

where in general formulae [1-1] and [1-2], R 5 to R 10 are each independently selected from the group consisting of a hydrogen atom, a cyano group, an amino group, an amide group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group and a hetero aryl group, R 5 and R 7 are optionally combined with each other to form a ring, R 8 and R 9 are optionally combined with each other to form a ring, n is an integer of 0 to 2, and
wherein in general formula [1-2], Z 1 and Z 2 are each independently selected from the group consisting of structures illustrated below, and each * indicates a bonding position,

2. The organic compound according to claim 1 , wherein R 3 is a hydrogen atom.

3. The organic compound according to claim 1 , wherein the organic compound is represented by general formula [4]:

where in general formula [4], X 1 is oxygen or sulfur,
wherein in general formula [4], each of Y 1 to Y 3 is a carbon atom or a nitrogen atom and is optionally the same or different, and wherein when one of Y 1 to Y 3 is a carbon atom, the carbon atom optionally has a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, and an alkyl group, and the alkyl group optionally has a halogen atom as a substituent.

4. The organic compound according to claim 1 , wherein in general formula [1], Y 1 to Y 3 are each a carbon atom.

5. The organic compound according to claim 1 , wherein in general formula [1], the at least one of Y 1 to Y 3 is a nitrogen atom.

6. The organic compound according to claim 5 , wherein Z 1 in formula [1-2] is a carbonyl group.

7. An organic electronic element comprising a pair of electrodes and an organic compound layer disposed between the pair of electrodes, wherein the organic compound layer contains the organic compound according to claim 1 .

8. A photoelectric conversion element comprising an electron-collecting electrode, a hole-collecting electrode, an organic compound layer disposed between the electron-collecting electrode and the hole-collecting electrode, wherein the organic compound layer contains the organic compound according to claim 1 .

9. The photoelectric conversion element according to claim 8 , wherein the organic compound layer includes a photoelectric conversion layer, and wherein the photoelectric conversion layer contains an organic n-type compound.

10. The photoelectric conversion element according to claim 9 , further comprising a second organic compound layer disposed between the hole-collecting electrode and the photoelectric conversion layer.

11. An image pickup element comprising a photoelectric conversion element according to claim 8 , a readout circuit connected to the photoelectric conversion element, and a signal processing circuit connected to the readout circuit.

12. The image pickup element according to claim 11 , wherein the photoelectric conversion element includes a second photoelectric conversion layer, and wherein the second photoelectric conversion layer photoelectrically converts light having a different wavelength from that of light photoelectrically converted by the photoelectric conversion layer.

13. An imaging device comprising: an imaging optical system and an imaging element that receives light passing through the image pickup optical system, wherein the imaging element is the imaging element according to claim 11 .

14. The imaging device according to claim 13 , further comprising a receiving unit that receives a signal from the outside, wherein the signal is a signal to control at least one of the imaging range, the start of an imaging operation, and the end of the imaging operation of the imaging device.

15. The imaging device according to claim 13 , further comprising a transmitting unit that transmits an acquired image to the outside.

16. An imaging device comprising the imaging element according to claim 11 and a housing that accommodates the imaging element, wherein the housing includes a connection portion that is connectable to an imaging optical system.

17. An organic compound represented by general formula [2]:

where in general formula [2], Ar 1 and Ar 2 are each independently selected from the group consisting of an aryl group and a heteroaryl group,
Ar 1 and Ar 2 each optionally have a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group as a substituent, the substituent optionally further has a halogen atom, a cyano group, an alkyl group, or an alkoxy group as a substituent, Ar 1 and Ar 2 are optionally combined with each other to form a ring,
wherein in general formula [2], R 1 and R 2 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, and a hetero aryl group, the alkyl group optionally has a halogen atom as a substituent,
each of the aryl group and the heteroaryl group each denoted by R 1 or R 2 optionally further has a halogen atom, a cyano group, an alkyl group, or an alkoxy group as a substituent, R 1 and R 2 are optionally combined with each other to form a ring,
where in general formula

Assignees

• Canon Kk

Inventors

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

Classifications

• C07D307/93

  condensed with a ring other than six-membered · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D333/78 Primary

  condensed with rings other than six-membered or with ring systems containing such rings · CPC title