# US 9,040,171 B2 · Organic light-emitting device

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- Number: US 9,040,171 B2
- Document ID: US9040171B2
- Status: Granted
- Kind: B2
- Application number: 13/103,863
- Filed: 2011-05-09
- Published: 2011-12-08
- Granted: 2015-05-26
- Earliest claimed: 2010-06-03
- Assignees: Samsung Display Co., Ltd.
- Applicants: Yoon-Hyun Kwak; Seok-Hwan Hwang; Young-Kook Kim; Hye-Jin Jung; Jong-Hyuk Lee; Hyung-Jun Song
- Inventors: Yoon-Hyun Kwak; Seok-Hwan Hwang; Young-Kook Kim; Hye-Jin Jung; Jong-Hyuk Lee; Hyung-Jun Song
- Web page: https://patentgrep.com/patent/US9040171B2

## CPC

- C07D 209/58: [b]- or [c]-condensed
- C07D 401/14: containing three or more hetero rings
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 417/10: linked by a carbon chain containing aromatic rings
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1037: with sulfur
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- H01L 51/0054
- H01L 51/0059
- H01L 51/0064
- H01L 51/0072
- H01L 51/0081
- H01L 51/0085
- H01L 51/0087
- H01L 51/5012
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H01L
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL

## Abstract

A heterocyclic compound represented by Formula 1 or Formula 2 below and an organic light-emitting device including the heterocyclic compound: wherein X1, X2, and R1 through R16 are defined as in the specification.

## Claims

### Claim 1

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode,
the organic layer comprising a first layer including a heterocyclic compound represented by Formula 1 below:
wherein X1 is a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C5-C50 arylthio group, a substituted or unsubstituted C5-C60 aryl group, a substituted amino group with a C5-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group; and R1 and R2 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 alkoxy group, a substituted or unsubstituted C5-C50 aryloxy group, a substituted or unsubstituted C5-C50 arylthio group, a substituted or unsubstituted C5-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group,
R5 is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; an unsubstituted C3-C60 heteroaryl group; a unsubstituted C5-C50 arylamine group; a substituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group which are substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; a substituted C3-C60 heteroaryl group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; or a substituted C5-C50 arylamine group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group and a halogen group,
R3, R4, and R6 -R8 are each independently a hydrogen atom or a heavy hydrogen atom.

### Claim 2

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode,
the organic layer comprising a first layer including a heterocyclic compound represented by Formula 2 below:
wherein X2 is a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C5-C50 arylthio group, a substituted or unsubstituted C5-C60 aryl group, a substituted amino group with a C5-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group; and R9 and R10 are each independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 alkoxy group, a substituted or unsubstituted C5-C50 aryloxy group, a substituted or unsubstituted C5-C50 arylthio group, a substituted or unsubstituted C5-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group,
R11, R12, and R14-R16 are each independently a hydrogen atom or a heavy hydrogen atom;
R13 is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; an unsubstituted C3-C60 heteroaryl group; a unsubstituted C5-C50 arylamine group; a substituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group which are substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; a substituted C3-C60 heteroaryl group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; or a substituted C5-C50 arylamine group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group and a halogen group.

### Claim 3 (depends on 1)

The organic light-emitting device of claim 1, wherein R1 and R2 are each independently a substituted or unsubstituted C6-C60 aryl group.

### Claim 4 (depends on 2)

The organic light-emitting device of claim 2, wherein R9 and R10 are each independently a substituted or unsubstituted C6-C60 aryl group.

### Claim 5 (depends on 1)

The organic light-emitting device of claim 1, wherein at least one of R1, R2 or R5 is a unsubstituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; an unsubstituted C3-C60 heteroaryl group; a unsubstituted C5-C50 arylamine group; a substituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group which are substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; a substituted C3-C60 heteroaryl group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; or a substituted C5-C50 arylamine group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group and a halogen group.

### Claim 6 (depends on 2)

The organic light-emitting device of claim 2, wherein at least one of R9, R10 or R13 is a unsubstituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; an unsubstituted C3-C60 heteroaryl group; a unsubstituted C5-C50 arylamine group; a substituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group which are substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; a substituted C3-C60 heteroaryl group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group or a halogen group; or a substituted C5-C50 arylamine group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group and a halogen group.

### Claim 7 (depends on 1)

The organic light-emitting device of claim 1, wherein X1 is a unsubstituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; an unsubstituted C3-C60 heteroaryl group; a substituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group which are substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group, a halogen group, or a C3-C10 heteroaryl group; or a substituted C3-C60 heteroaryl group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group, a halogen group or a C3-C10 heteroaryl group.

### Claim 8 (depends on 2)

The organic light-emitting device of claim 2, wherein X2 is a unsubstituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; an unsubstituted C3-C60 heteroaryl group; a substituted monocyclic to tetracyclic aryl group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group which are substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group, a halogen group, or a C3-C10 heteroaryl group; or a substituted C3-C60 heteroaryl group which is substituted with a C1-C5 alkyl group, a C1-C5 alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group, a halogen group or a C3-C10 heteroaryl group.

### Claim 9 (depends on 1)

The organic light-emitting device of claim 1, wherein R1 and R2, are each independently a methyl group or a phenyl group.

### Claim 10 (depends on 2)

The organic light-emitting device of claim 2, wherein R9 and R10 are each independently a methyl group or a phenyl group.

### Claim 11 (depends on 1)

The organic light-emitting device of claim 1, comprising one of the compounds below:

### Claim 12 (depends on 2)

The organic light-emitting device of claim 2, comprising one of the compounds below:

### Claim 13 (depends on 1)

The organic light-emitting device of claim 1, wherein the first layer comprises an electron injection layer, an electron transport layer a single film having both an electron injection function and an electron transport function, or an emission layer.

### Claim 14 (depends on 2)

The organic light-emitting device of claim 2, wherein the first layer comprises an electron injection layer, an electron transport layer a single film having both an electron injection function and an electron transport function, or an emission layer.

### Claim 15 (depends on 1)

The organic light-emitting device of claim 1, wherein the first layer comprises an emission layer, and the heterocyclic compound is used as a host or dopant for a fluorescent or phosphorescent device.

### Claim 16 (depends on 2)

The organic light-emitting device of claim 2, wherein the first layer comprises an emission layer, and the heterocyclic compound is used as a host or dopant for a fluorescent or phosphorescent device.

### Claim 17 (depends on 1)

The organic light-emitting device of claim 1, wherein the first layer comprises at least one of an emission layer, an electron injection layer or an electron transport layer, and wherein the emission layer comprises an anthracene compound, an arylamine compound, or a styryl compound.

### Claim 18 (depends on 2)

The organic light-emitting device of claim 2, wherein the first layer comprises an emission layer, an electron injection layer or an electron transport layer, and the emission layer comprises an anthracene compound, an arylamine compound, or a styryl compound.

### Claim 19 (depends on 1)

The organic light-emitting device of claim 1, wherein the first layer comprises at least of one of an emission layer, an electron injection layer or an electron transport layer, and wherein the emission layer comprises a red emission layer, a green emission layer, a blue emission layer or a white emission layer that comprises a phosphorescent compound.

### Claim 20 (depends on 2)

The organic light-emitting device of claim 2, wherein the first layer comprises an emission layer, an electron injection layer or an electron transport layer, and the emission layer comprises a red emission layer, a green emission layer, a blue emission layer or a white emission layer that comprises a phosphorescent compound.

### Claim 21 (depends on 1)

The organic light-emitting device of claim 1, wherein the organic layer further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a functional layer having both hole injection and transport functions, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer and a combination of at least two of these layers.

### Claim 22 (depends on 21)

The organic light-emitting device of claim 21, wherein at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and transport functions further comprises a charge-generating material.

### Claim 23 (depends on 21)

The organic light-emitting device of claim 21, wherein the electron transport layer comprises an electron transporting organic material and a metal-containing material.

### Claim 24 (depends on 23)

The organic light-emitting device of claim 23, wherein the metal-containing material comprises a lithium complex.

### Claim 25 (depends on 2)

The organic light-emitting device of claim 2, wherein the organic layer further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a functional layer having both hole injection and transport functions, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer and a combination of at least two of these layers.

### Claim 26 (depends on 25)

The organic light-emitting device of claim 25, wherein at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and transport functions further comprises a charge-generating material.

### Claim 27 (depends on 25)

The organic light-emitting device of claim 25, wherein the electron transport layer comprises an electron transporting organic material and a metal-containing material.

### Claim 28 (depends on 27)

The organic light-emitting device of claim 27, wherein the metal-containing material comprises a lithium complex.

### Claim 29 (depends on 21)

The organic light-emitting device of claim 21, having a first electrode/hole injection layer/emission layer/second electrode structure, a first electrode/hole injection layer/hole transport layer/emission layer/electron transport layer/second electrode structure, or a first electrode/hole injection layer/hole transport layer/emission layer/electron transport structure layer/electron injection layer/second electrode structure.

### Claim 30 (depends on 25)

The organic light-emitting device of claim 25, having a first electrode/hole injection layer/emission layer/second electrode structure, a first electrode/hole injection layer/hole transport layer/emission layer/electron transport layer/second electrode structure, or a first electrode/hole injection layer/hole transport layer/emission layer/electron transport structure layer/electron injection layer/second electrode structure.

### Claim 31 (depends on 1)

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, wherein the organic layer comprises at least one layer comprising the heterocyclic compound of claim 1, the at least one layer being formed using a wet process.

### Claim 32 (depends on 2)

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, wherein the organic layer comprises at least one layer comprising the heterocyclic compound of claim 2, the at least one layer being formed using a wet process.

### Claim 33 (depends on 1)

A flat panel display device comprising the organic light-emitting device of claim 1, wherein the first electrode of the organic light-emitting device is electrically connected to a source electrode or a drain electrode of a thin-film transistor.

### Claim 34 (depends on 2)

A flat panel display device comprising the organic light-emitting device of claim 2, wherein the first electrode of the organic light-emitting device is electrically connected to a source electrode or a drain electrode of a thin-film transistor.