# US 2014/0151650 A1 · Heterocyclic compound and organic light-emitting device including the same

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- Number: US 2014/0151650 A1
- Document ID: US20140151650A1
- Status: Published application
- Kind: A1
- Application number: 14/012,545
- Filed: 2013-08-28
- Published: 2014-06-05
- Earliest claimed: 2012-12-04
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Jung-Sub Lee
- Web page: https://patentgrep.com/patent/US20140151650A1

## CPC

- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- C07D 471/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07F 7/0812: {comprising a heterocyclic ring}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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)

## Abstract

A heterocyclic compound represented by Formula 1 below and an organic light-emitting device including the heterocyclic compound are described. In Formula 1, R1 to R4 may be each independently one of a hydrogen atom, a deuterium atom, C5-C60 alkyl, C5-C60 aryl and C6-C60 condensed polycyclic; L1 and L2 may be each independently one of a single bond, C5-C60 aryl, C3-C60 heteroaryl and C6-C60 condensed polycyclic; Ar1 and Ar2 may be each independently one of C5-C60 aryl, C3-C60 heteroaryl and C6-C60 condensed polycyclic; A, B, C and D may be each independently one of —CH═ and —N═, excluding that all A, B, C and D are —CH═; and m and n may be each independently an integer of 0 to 3, excluding that all m and n are zero, wherein any of the above alkyl groups, aryl groups, condensed polycyclic groups and heteroaryl groups may be substituted or unsubstituted.

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1 below:
R1 to R4 in Formula 1 being each independently one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C5-C60 alkyl group, a substituted or unsubstituted C5-C60 aryl group and a substituted or unsubstituted C6-C60 condensed polycyclic group;
L1 and L2 in Formula 1 being each independently one of a single bond, a substituted or unsubstituted C5-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group and a substituted or unsubstituted C6-C60 condensed polycyclic group;
Ar1 and Ar2 in Formula 1 being each independently a substituted or unsubstituted C5-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group and a substituted or unsubstituted C6-C60 condensed polycyclic group;
A, B, C, and D in Formula 1 being each independently one of —CH═ and —N═, excluding that all A, B, C, and D are —CH═; and
m and n in Formula 1 being each independently an integer of 0 to 3, excluding that all m and n are zero.

### Claim 2 (depends on 1)

The heterocyclic compound of claim 1, R1 to R4 in Formula 1 each being independently one of a hydrogen atom and a deuterium atom.

### Claim 3 (depends on 1)

The heterocyclic compound of claim 1, L1 and L2 in Formula 1 each being independently one of a single bond and a group represented by one of Formulae 2a to 2c below:
Q1 in Formula 2c being —CR30R31;
R30 and R31 being each independently one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, halogen group, a cyano group, a nitro group, a hydroxy group and a carboxy group; and
* indicates a binding site.

### Claim 4 (depends on 1)

The heterocyclic compound of claim 1, Ar1 and Ar2 in Formula 1 being each independently a group represented by one of Formulae 3a to 3j below:
Q2 to Q5 in Formulae 3a to 3j being each independently one of —CR30R31—, —NR32—, —S— and —O—;
Z1, Z2, R30, R31, and R32 in Formulae 3a to 3j being each independently one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-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 C3-C20 heteroaryl group or a C5-C20 aryl group, a halogen group, a cyano group, a nitro group, a hydroxy group, —Si(R40)3 and a carboxy group;
R40 being one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group and a substituted or unsubstituted C6-C20 condensed polycyclic group;
Y1, Y2, and Y3 being each independently one of —CH═ and —N═;
p in Formulae 3a and 3c-3f being an integer of 1 to 9; and
* indicating a binding site.

### Claim 5 (depends on 1)

The heterocyclic compound of claim 1, A and D in Formula 1 all being —N═; and B and C all being —CH═.

### Claim 6 (depends on 1)

The heterocyclic compound of claim 1, the heterocyclic compound of Formula 1 being one of Compounds 1 to 30 below:

### 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, the organic layer comprising the heterocyclic compound of claim 1.

### Claim 8 (depends on 7)

The organic light-emitting device of claim 7, the organic layer comprising an emission layer.

### Claim 9 (depends on 7)

The organic light-emitting device of claim 7, the organic light-emitting device comprising: an emission layer; at least one of an electron injection layer, an electron transport layer and a functional layer having both electron injection and transport capabilities; and at least one of a hole injection layer, a hole transport layer and a functional layer having both hole injection and transport capabilities,
the emission layer comprising the heterocyclic compound, the emission layer further comprising at least one of an anthracene-based compound, an arylamine-based compound and a styryl-based compound.

### Claim 10 (depends on 7)

The organic light-emitting device of claim 7, the organic light-emitting device comprising: an emission layer; at least one of an electron injection layer, an electron transport layer and a functional layer having both electron injection and transport capabilities; and at least one of a hole injection layer, a hole transport layer and a functional layer having both hole injection and transport capabilities,
the emission layer comprising the heterocyclic compound,
the emission layer comprising red, green, blue, and white emission layers, one of which comprises a phosphorescent compound.

### Claim 11 (depends on 10)

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

### Claim 12 (depends on 11)

The organic light-emitting device of claim 11, the charge-generating material being a p-dopant.

### Claim 13 (depends on 12)

The organic light-emitting device of claim 12, the p-dopant being a quinone derivative.

### Claim 14 (depends on 12)

The organic light-emitting device of claim 12, the p-dopant being a metal oxide.

### Claim 15 (depends on 12)

The organic light-emitting device of claim 12, the p-dopant being a cyano group-containing compound.

### Claim 16 (depends on 7)

The organic light-emitting device of claim 7, the organic layer comprising an electron transport layer, the electron transport layer comprising a metal complex.

### Claim 17 (depends on 16)

The organic light-emitting device of claim 16, the metal complex being a Li complex.

### Claim 18 (depends on 16)

The organic light-emitting device of claim 16, the metal complex being compound 203 below:

### Claim 19 (depends on 7)

The organic light-emitting device of claim 7, the organic layer being formed from the heterocyclic compound using a wet process.

### Claim 20 (depends on 7)

A flat panel display device comprising the organic light-emitting device of claim 7, the first electrode of the organic light-emitting device being electrically connected to one of a source electrode and a drain electrode of a thin-film transistor.