# US 12,215,066 B2 · Organic photodetector and electronic device including the same

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- Number: US 12,215,066 B2
- Document ID: US12215066B2
- Status: Granted
- Kind: B2
- Application number: 17/674,751
- Filed: 2022-02-17
- Published: 2022-12-22
- Granted: 2025-02-04
- Earliest claimed: 2021-06-01
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Seokgyu Yoon; Dongkyu Seo; Junyong Shin; Byeongwook Yoo; Daeho Lee; Byungseok Lee
- Web page: https://patentgrep.com/patent/US12215066B2

## CPC

- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- C07C 209/86: Separation
- C07C 211/49: having at least two amino groups bound to the carbon skeleton
- C07C 211/57: having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- C07D 235/18: with aryl radicals directly attached in position 2
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 251/24: to three ring carbon atoms
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 471/04: Ortho-condensed systems
- C07D 487/14: Ortho-condensed systems
- C07F 5/069: {without C-aluminium linkages}
- H10K 30/81: Electrodes
- H10K 65/00: Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element and at least one organic radiation-sensitive element, e.g. organic opto-couplers (organic image sensors integrated with organic light-emitting devices H10K39/34; OLED displays integrated with photosensors H10K59/13)
- H10K 85/211: {Fullerenes, e.g. C60}
- H10K 85/322: {comprising boron}
- H10K 30/20: comprising organic-organic junctions, e.g. donor-acceptor junctions
- H10K 85/221: {Carbon nanotubes}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## 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.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 2)

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.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 7)

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,
L201 to L204 are each, independently from one another, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
L205 is *—O—*′, *—S—*′, *—N(Q201)-*′, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C2-C20 alkenylene group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xa1 to xa4 are each, independently from one another, an integer from 0 to 5,
xa5 is an integer from 1 to 10,
R201 to R204 and Q201 are each, independently from one another, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
R201 and R202 are optionally linked to each other, via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a,
R203 and R204 are optionally linked to each other, via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a,
na1 is an integer from 1 to 4, and
R10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 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 C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11),
—S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), wherein Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each, independently from one another: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy so group; or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

### Claim 9 (depends on 7)

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. %.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 12)

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.

### Claim 14 (depends on 1)

The organic photodetector of claim 1, wherein the organic photodetector has a dark current density of about 1×10−4 mA/cm2 or less when a reverse bias of −3V is applied.

### Claim 15 (depends on 1)

The organic photodetector of claim 1, wherein the organic photodetector does not comprise an electron blocking layer between the first electrode and the activation layer.

### Claim 16 (depends on 1)

The organic photodetector of claim 1, wherein the first electrode comprises an anode,
the second electrode comprises a cathode,
the organic photodetector further comprises an electron transport region between the activation layer and the second electrode, and
the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

### Claim 17 (depends on 16)

The organic photodetector of claim 16, wherein the electron transport region comprises the hole blocking layer, the electron transport layer, and the electron injection layer arranged sequentially from the activation layer.

### Claim 18 (depends on 1)

An electronic apparatus comprising the organic photodetector of claim 1.

### Claim 19 (depends on 18)

The electronic apparatus of claim 18, further comprising a light-emitting device.

### Claim 20

An electronic apparatus comprising:
a substrate comprising a light detection region and a light emission region;
an organic photodetector on the light detection region; and
a light-emitting device on the light emission region,
wherein the organic photodetector comprises: a first pixel electrode; a second electrode facing the first pixel electrode; and a hole injection layer, a hole transport layer, and an activation layer arranged sequentially between the first pixel electrode and the second electrode, 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,
the light-emitting device comprises: a second pixel electrode; the second electrode facing the second pixel electrode; and the hole injection layer, the second hole transport layer, and an emission layer arranged sequentially between the second pixel electrode and the second electrode,
the first pixel electrode, the first hole transport layer, and the activation layer at least partially overlap the light detection region,
the second pixel electrode and the emission layer at least partially overlap the light emission region, and
the hole injection layer, the second hole transport layer, and the counter electrode overlap substantially the entirety of the light detection region and the light emission region.