# US 2021/0242403 A1 · Light-emitting device including hole transport region containing group 11 metal chalcogenide compound

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- Number: US 2021/0242403 A1
- Document ID: US20210242403A1
- Status: Published application
- Kind: A1
- Application number: 16/997,770
- Filed: 2020-08-19
- Published: 2021-08-05
- Earliest claimed: 2020-01-31
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Hyunmi DOH; Jaehoon KIM; Jaehong PARK
- Web page: https://patentgrep.com/patent/US20210242403A1

## CPC

- C09K 11/70: containing phosphorus
- H10K 50/17: Carrier injection layers
- H10K 50/805: Electrodes
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 50/115: comprising active inorganic nanostructures, e.g. luminescent quantum dots
- H10K 50/15: Hole transporting layers
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 2102/00: Constructional details relating to the organic devices covered by this subclass
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an interlayer between the first electrode and the second electrode and including an emission layer, wherein the interlayer includes i) a hole transport region between the first electrode and the emission layer, and ii) an electron transport region between the emission layer and the second electrode, and the hole transport region includes a Group 11 metal chalcogenide compound including a Group 11 metal and a chalcogenide element with the proviso that oxygen is excluded from the chalcogenide element.

## Claims

### Claim 1

A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an interlayer between the first electrode and the second electrode and comprising an emission layer,
wherein the interlayer comprises:
i) a hole transport region between the first electrode and the emission layer, and
ii) an electron transport region the emission layer and the second electrode,
wherein the hole transport region comprises a Group 11 metal chalcogenide compound comprising a Group 11 metal and a chalcogenide element with the proviso oxygen is excluded from the chalcogenide element.

### Claim 2 (depends on 1)

The light-emitting device of claim 1, wherein:
the first electrode is an anode,
the second electrode is a cathode, and
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.

### Claim 3 (depends on 1)

The light-emitting device of claim 1, wherein:
the first electrode is an anode,
the second electrode is a cathode, and
the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

### Claim 4 (depends on 1)

The light-emitting device of claim 1, wherein the Group 11 metal is Cu.

### Claim 5 (depends on 1)

The light-emitting device of claim 1, wherein the Group 11 metal chalcogenide compound comprises Cu2S, CuS, Cu2Se, CuSe, Cu2Te, CuTe, or any combination thereof.

### Claim 6 (depends on 1)

The light-emitting device of claim 1, wherein the hole transport region comprises a hole injection layer and a hole transport layer, and
the hole injection layer comprises the Group 11 metal chalcogenide compound.

### Claim 7 (depends on 1)

The light-emitting device of claim 1, wherein the hole transport region comprises a hole injection layer and a hole transport layer, and
the hole transport layer comprises the Group 11 metal chalcogenide compound and a hole transport compound.

### Claim 8 (depends on 7)

The light-emitting device of claim 7, wherein the hole transport compound comprises a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
wherein, in Formulae 201 and 202,
L201 to L204 are each independently a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
L205 is *—O—*′, *—S—*′, *—N(Q201)-*′, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xa1 to xa4 are each independently 0, 1, 2, or 3,
xa5 is an integer from 1 to 10,
R201 to R204 and Q201 are each independently a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
at least one substituent selected from the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C1-C20 alkylene group, the substituted C2-C20 alkenylene group, the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted bivalent non-aromatic condensed polycyclic group, and the substituted bivalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

### Claim 9 (depends on 7)

The light-emitting device of claim 7, wherein the hole transport compound is at least one selected from the following compounds:

### Claim 10 (depends on 1)

The light-emitting device of claim 1, wherein the hole transport region comprises a hole transport layer and a charge generating layer,
the charge generating layer is between the emission layer and the hole transport layer, and
the charge generating layer comprises the Group 11 metal chalcogenide compound.

### Claim 11 (depends on 10)

The light-emitting device of claim 10, wherein the Group 11 metal chalcogenide compound comprises Cu2Se, CuSe, or any combination thereof.

### Claim 12 (depends on 1)

The light-emitting device of claim 1, wherein the Group 11 metal chalcogenide compound has a size of about 0.2 nm to about 100 nm.

### Claim 13 (depends on 1)

The light-emitting device of claim 1, wherein the emission layer comprises quantum dots.

### Claim 14 (depends on 1)

The light-emitting device of claim 1, wherein the emission layer comprises:
a Group III-VI semiconductor compound; a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.

### Claim 15 (depends on 14)

The light-emitting device of claim 14, wherein the Group III-VI semiconductor compound comprises In2S3, AgInS, AgInS2, CuInS, CuInS2, or any combination thereof.

### Claim 16 (depends on 14)

The light-emitting device of claim 14, wherein the Group II-VI semiconductor compound comprises CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, or any combination thereof.

### Claim 17 (depends on 14)

The light-emitting device of claim 14, wherein the Group III-V semiconductor compound comprises GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, or any combination thereof.

### Claim 18 (depends on 14)

The light-emitting device of claim 14, wherein the Group IV-VI semiconductor compound comprises SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, SnPbSTe, or any combination thereof.

### Claim 19 (depends on 14)

The light-emitting device of claim 14, wherein the Group IV element or compound comprises Si, Ge, SiC, SiGe, or any combination thereof.

### Claim 20 (depends on 1)

An electronic apparatus comprising a thin-film transistor and the light-emitting device of claim 1,
wherein the thin-film transistor comprises a source electrode, a drain electrode, an activation layer, and a gate electrode, and
the first electrode of the light-emitting device is in electrical contact with one of the source electrode and the drain electrode of the thin-film transistor.