# US 2025/0098535 A1 · Organic electroluminescence device and amine compound for organic electroluminescence device

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- Number: US 2025/0098535 A1
- Document ID: US20250098535A1
- Status: Published application
- Kind: A1
- Application number: 18/960,958
- Filed: 2024-11-26
- Published: 2025-03-20
- Earliest claimed: 2020-01-15
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Taku IMAIZUMI
- Web page: https://patentgrep.com/patent/US20250098535A1

## CPC

- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C07D 493/04: Ortho-condensed systems
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- 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 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 50/15: Hole transporting layers
- H10K 50/156: {comprising a multilayered structure}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

An organic electroluminescence device of an embodiment includes a first electrode, a second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one layer among the plurality of organic layers includes an amine compound represented by Formula 1, and the device thereby shows high emission efficiency and improved life span characteristics:

## Claims

### Claim 1

An organic electroluminescence device, comprising:
a first electrode;
a second electrode opposite to the first electrode; and
a plurality of organic layers between the first electrode and the second electrode, wherein at least one functional layer selected from among the plurality of organic layers comprises an amine compound represented by any one of Formula 3-1 to Formula 3-3:
wherein in Formula 3-1,
X is O or S,
Y is O or S, where at least one of X or Y is O,
R1 and R2 are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
at least one of R1 or R2 comprises a substituted or unsubstituted cyclohexyl group or a substituted or unsubstituted adamantyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted naphthobenzofuran, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted dibenzothiophene group, a phenyl group substituted with a deuterium atom, a halogen atom, an oxy group, a naphthalene group, or a pyridine,
wherein in Formulae 3-2 and 3-3,
X is O or S,
Y is O or S, where one of X and Y is S and the other is O,
R1 and R2 are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, and
wherein in Formulae 3-1 to 3-3,
R3 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, excluding a carbazolyl group,
L is a direct linkage, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
“m” is an integer of 0 to 4, and
“n” is an integer of 0 to 4.

### Claim 2 (depends on 1)

The organic electroluminescence device of claim 1, wherein the amine compound is a monoamine compound.

### Claim 3 (depends on 1)

The organic electroluminescence device of claim 1, wherein in Formulae 3-2 and 3-3, R1 and R2 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.

### Claim 4 (depends on 1)

The organic electroluminescence device of claim 1, wherein R1 and R2 are each independently a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group,
provided that in Formula 3-1, at least one of R1 or R2 comprises a substituted or unsubstituted cyclohexyl group or a substituted or unsubstituted adamantyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted naphthobenzofuran, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted dibenzothiophene group, a phenyl group substituted with a deuterium atom, a halogen atom, an oxy group, a naphthalene group, or a pyridine.

### Claim 5 (depends on 1)

The organic electroluminescence device of claim 1, wherein L is a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.

### Claim 6 (depends on 1)

The organic electroluminescence device of claim 1, wherein R4 and R5 are each independently a hydrogen atom, a deuterium atom, or a phenyl group.

### Claim 7 (depends on 1)

The organic electroluminescence device of claim 1, wherein the amine compound is represented by any one of Formula 4-2 and Formula 4-4 to Formula 4-9:
and
wherein in Formula 4-2 and Formula 4-4 to Formula 4-9,
R1 to R5, L, “m” and “n” are each independently as defined in Formula 3-1 to Formula 3-3,
provided that in Formulae 4-2, 4-6, and 4-7, at least one of R1 or R2 comprises a substituted or unsubstituted cyclohexyl group or a substituted or unsubstituted adamantyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted naphthobenzofuran, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted dibenzothiophene group, a phenyl group substituted with a deuterium atom, a halogen atom, an oxy group, a naphthalene group, or a pyridine.

### Claim 8 (depends on 1)

The organic electroluminescence device of claim 1, wherein the plurality of organic layers comprise a hole transport region, an emission layer, and an electron transport region, and
the hole transport region comprises the amine compound.

### Claim 9 (depends on 8)

The organic electroluminescence device of claim 8, wherein the hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer, and
the hole transport layer comprises the amine compound.

### Claim 10 (depends on 1)

The organic electroluminescence device of claim 1, wherein the amine compound is at least one compound of Compound Group A to Compound Group F:

### Claim 11

An amine compound represented by any one of Formula 3-1 to Formula 3-3:
wherein in Formula 3-1,
X is O or S,
Y is O or S, where at least one of X or Y is O,
R1 and R2 are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
at least one of R1 or R2 comprises a substituted or unsubstituted cyclohexyl group or a substituted or unsubstituted adamantyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted naphthobenzofuran, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted dibenzothiophene group, a phenyl group substituted with a deuterium atom, a halogen atom, an oxy group, a naphthalene group, or a pyridine,
wherein in Formulae 3-2 and 3-3,
X is O or S,
Y is O or S, where one of X and Y is S and the other is O,
R1 and R2 are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, and
wherein in Formulae 3-1 to 3-3,
R3 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, excluding a carbazolyl group,
L is a direct linkage, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
“m” is an integer of 0 to 4, and
“n” is an integer of 0 to 4.

### Claim 12 (depends on 11)

The amine compound of claim 11, wherein the amine compound is a monoamine compound.

### Claim 13 (depends on 11)

The amine compound of claim 11, wherein in Formulae 3-2 and 3-3, R1 and R2 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.

### Claim 14 (depends on 11)

The amine compound of claim 11, wherein R1 and R2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted fluorenyl group,
provided that in Formula 3-1, at least one of R1 or R2 comprises a substituted or unsubstituted cyclohexyl group or a substituted or unsubstituted adamantyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted naphthobenzofuran, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted dibenzothiophene group, a phenyl group substituted with a deuterium atom, a halogen atom, an oxy group, a naphthalene group, or a pyridine.

### Claim 15 (depends on 11)

The amine compound of claim 11, wherein L is a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.

### Claim 16 (depends on 11)

The amine compound of claim 11, wherein the amine compound is represented by any one of Formula 4-2 and Formula 4-4 to Formula 4-9:
and
wherein in Formula 4-2 and Formula 4-4 to Formula 4-9,
R1 to R5, L, “m” and “n” are each independently as defined in Formula 3-1 to Formula 3-3,
provided that in Formulae 4-2, 4-6, and 4-7, at least one of R1 or R2 comprises a substituted or unsubstituted cyclohexyl group or a substituted or unsubstituted adamantyl group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted naphthobenzofuran, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted dibenzothiophene group, a phenyl group substituted with a deuterium atom, a halogen atom, an oxy group, a naphthalene group, or a pyridine.

### Claim 17

An amine compound comprising at least one compound of Compound Group A to Compound Group F: