Organic photodetector and electronic device including the same

Patent metadata

Field	Value
Publication number	US-12215066-B2
Application number	US-202217674751-A
Country	US
Kind code	B2
Filing date	Feb 17, 2022
Priority date	Jun 1, 2021
Publication date	Feb 4, 2025
Grant date	Feb 4, 2025

Abstract

An organic photodetector includes: a first electrode; a second electrode facing the first electrode; an activation layer between the first electrode and the second electrode; a hole injection layer between the first electrode and the activation layer; and a hole transport layer between the hole injection layer and the activation layer, wherein the hole transport layer includes: a first hole transport layer including a p-dopant; and a second hole transport layer not including a p-dopant.

First claim

What is claimed is:

1. An organic photodetector comprising:
a first electrode;
a second electrode facing the first electrode;
an activation layer between the first electrode and the second electrode;
a hole injection layer between the first electrode and the activation layer; and
a hole transport layer between the hole injection layer and the activation layer,
wherein the hole transport layer comprises: a first hole transport layer including a p-dopant; and a second hole transport layer not including a p-dopant.

2. The organic photodetector of claim 1 , wherein the first hole transport layer is disposed in the middle of the second hole transport layer, and
a distance between a surface of the first electrode facing the second electrode and a surface of the first hole transport layer facing the first electrode is about 450 Å to about 1200 Å.

3. The organic photodetector of claim 2 , wherein the distance between the surface of the first electrode facing the second electrode and the surface of the first hole transport layer facing the first electrode is about 450 Å to about 650 Å, or about 900 Å to about 1200 Å.

4. The organic photodetector of claim 1 , wherein the first hole transport layer is between the hole injection layer and the second hole transport layer, and the hole injection layer and the second hole transport layer are in direct contact with each other.

5. The organic photodetector of claim 1 , wherein the first hole transport layer is between the second hole transport layer and the activation layer, and the second hole transport layer and the activation layer are in direct contact with each other.

6. The organic photodetector of claim 1 , wherein the p-dopant comprises a compound having a lowest unoccupied molecular orbital energy level of less than about −3.5 eV.

7. The organic photodetector of claim 1 , wherein the first hole transport layer further comprises a hole transport material.

8. The organic photodetector of claim 7 , wherein the hole transport material comprises a compound of Formula 202 or any combination of compounds of Formula 202:

wherein, in Formulae 201 and 202,
L 201 to L 204 are each, independently from one another, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
L 205 is *—O—*′, *—S—*′, *—N(Q 201 )-*′, a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 2 -C 20 alkenylene group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
xa1 to xa4 are each, independently from one another, an integer from 0 to 5,
xa5 is an integer from 1 to 10,
R 201 to R 204 and Q 201 are each, independently from one another, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
R 201 and R 202 are optionally linked to each other, via a single bond, a C 1 -C 5 alkylene group unsubstituted or substituted with at least one R 10a , or a C 2 -C 5 alkenylene group unsubstituted or substituted with at least one R 10a , to form a C 8 -C 60 polycyclic group unsubstituted or substituted with at least one R 10a ,
R 203 and R 204 are optionally linked to each other, via a single bond, a C 1 -C 5 alkylene group unsubstituted or substituted with at least one R 10a , or a C 2 -C 5 alkenylene group unsubstituted or substituted with at least one R 10a , to form a C 8 -C 60 polycyclic group unsubstituted or substituted with at least one R 10a ,
na1 is an integer from 1 to 4, and
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group each independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ),

—S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, or a C 2 -C 60 heteroaryl alkyl group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each, independently from one another: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy so group; or a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 7 -C 60 aryl alkyl group, or a C 2 -C 60 heteroaryl alkyl group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

9. The organic photodetector of claim 7 , wherein an amount of the p-dopant in the first hole transport layer is about 0.1 vol. % to about 10 vol. %.

10. The organic photodetector of claim 1 , wherein the first hole transport layer has a thickness of about 5 Å to about 150 Å.

11. The organic photodetector of claim 1 , wherein the activation layer comprises: a p-type semiconductor layer including a p-type organic semiconductor; and an n-type semiconductor layer including an n-type organic semiconductor, and
the p-type semiconductor layer and the n-type semiconductor layer form a PN junction.

12. The organic photodetector of claim 1 , wherein the activation layer comprises: a p-type semiconductor layer including a p-type organic semiconductor; and an n-type semiconductor layer including an n-type organic semiconductor, and
a mixed layer of the p-type organic semiconductor and the n-type organic semiconductor.

13. The organic photodetector of claim 12 , wherein
the p-type organic semiconductor comprises SubPc, CuPc, DBP, or any combination thereof, and
the n-type organic semiconductor comprises C60 fullerene, C70 fullerene, or any combination thereof.

14. The organic photodetector of claim 1 , wherein the organic photodetector has a dark current density of about 1×10 −4 mA/cm 2 or less when a reverse bias of −3V is applied.

15. The organic photodetector of claim 1 , wherein the organic photodetector does not comprise an electron blocking

Assignees

• Samsung Display Co Ltd

Inventors

• Yoon Seokgyu
• Seo Dongkyu
• Shin Junyong
• Yoo Byeongwook
• Lee Daeho
• Lee Byungseok

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07F5/069

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• C07D487/14

  Ortho-condensed systems · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D409/12

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