# US 9,437,827 B2 · Heterocyclic compound and organic light-emitting device including the same

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- Number: US 9,437,827 B2
- Document ID: US9437827B2
- Status: Granted
- Kind: B2
- Application number: 14/220,695
- Filed: 2014-03-20
- Published: 2015-01-01
- Granted: 2016-09-06
- Earliest claimed: 2013-06-26
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Seok-Hwan Hwang; Young-Kook Kim; Jun-Ha Park; Hye-Jin Jung; Jin-O Lim; Eun-Young Lee; Sang-Hyun Han; Eun-Jae Jeong; Soo-Yon Kim; Jong-Hyuk Lee
- Web page: https://patentgrep.com/patent/US9437827B2

## CPC

- C09K 11/06: containing organic luminescent materials
- H10K 50/15: Hole transporting layers
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1466: containing nitrogen as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/155: comprising dopants
- H10K 50/16: Electron transporting layers
- H10K 2101/10: Triplet emission
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A heterocyclic compound represented by Formula 1 below and an organic light-emitting device including the same,

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1, below:
wherein, in Formula 1, R1 to R8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group.

### Claim 2 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein R1 and R2 in Formula 1 are each independently a substituted or unsubstituted C1-C20 alkyl group, or a group represented by one of Formulae 2a to 2e, below:
wherein, in Formulae 2a to 2e,
Y1, Y2, and Y3 are each independently CH or N;
Q1 is a linker represented by —CR50R51— or —NR52—;
Z1, Z2, R50, R51, and R52 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, an amino group substituted with a C6-C20 aryl group or a C3-C20 heteroaryl group, a halogen group, a cyano group, a nitro group, a hydroxy group, or a carboxyl group; and
* indicates a binding site;
wherein, in Formulae 2b and 2c, p is an integer of 1 to 7; and
wherein, in Formulae 2d and 2e, p is an integer of 1 to 9.

### Claim 3 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein R3, R4, R7, and R8 in Formula 1 are each independently a hydrogen atom, a deuterium atom, or
wherein:
Z1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, an amino group substituted with a C6-C20 aryl group or a C3-C20 heteroaryl group, a halogen group, a cyano group, a nitro group, a hydroxy group, or a carboxyl group;
p is an integer from 1 to 5; and
* indicates a binding site.

### Claim 4 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein R5 and R6 in Formula 1 are each independently a hydrogen atom or a deuterium atom.

### Claim 5 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein R3, R4, R5, R6, R7, and R8 in Formula 1 are each independently a hydrogen atom or a deuterium atom.

### Claim 6 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Formula 1 is one of the following compounds:

### Claim 7 (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 includes the heterocyclic compound as claimed in claim 1.

### Claim 8 (depends on 7)

The organic light-emitting device as claimed in claim 7, wherein the organic layer is an emission layer or an electron transport layer.

### Claim 9 (depends on 7)

The organic light-emitting device as claimed in claim 7, wherein:
the organic layer includes an emission layer, and further includes at least one of an electron injection layer, an electron transport layer, a functional layer having both electron injection and transport capabilities, a hole injection layer, a hole transport layer, or a functional layer having both hole injection and transport capabilities, and
the emission layer includes an anthracene-based compound, an arylamine-based compound, or a styryl-based compound.

### Claim 10 (depends on 7)

The organic light-emitting device as claimed in claim 7, wherein:
the organic layer includes an emission layer, and further includes at least one of an electron injection layer, an electron transport layer, a functional layer having both electron injection and transport capabilities, a hole injection layer, a hole transport layer, or a functional layer having both hole injection and transport capabilities, and
the emission layer includes red, green, blue, and white emission layers, one of which includes a phosphorescent compound.

### Claim 11 (depends on 10)

The organic light-emitting device as claimed in claim 10, wherein:
the organic layer includes at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capabilities, and
the at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capabilities includes a charge-generating material.

### Claim 12 (depends on 11)

The organic light-emitting device as claimed in claim 11, wherein the charge-generating material is a p-type dopant.

### Claim 13 (depends on 12)

The organic light-emitting device as claimed in claim 12, wherein the p-type dopant is a quinone derivative.

### Claim 14 (depends on 12)

The organic light-emitting device as claimed in claim 12, wherein the p-type dopant is a metal oxide.

### Claim 15 (depends on 12)

The organic light-emitting device as claimed in claim 12, wherein the p-type dopant is a cyano group-containing compound.

### Claim 16 (depends on 7)

The organic light-emitting device as claimed in claim 7, wherein the organic layer includes an electron transport layer, the electron transport layer further including a metal-containing material.

### Claim 17 (depends on 16)

The organic light-emitting device as claimed in claim 16, wherein the metal-containing material is a Li complex.

### Claim 18 (depends on 16)

The organic light-emitting device as claimed in claim 16, wherein the metal-containing material includes one of lithium quinolate (LiQ) or Compound 203 below:

### Claim 19 (depends on 7)

The organic light-emitting device as claimed in claim 7, wherein the organic layer is formed of the heterocyclic compound by a wet process.

### Claim 20 (depends on 7)

A flat panel display device comprising the organic light-emitting device as claimed in claim 7, 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.