# US 8,771,844 B2 · Heterocyclic compound and organic light-emitting diode and flat display device including the heterocyclic compound

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- Number: US 8,771,844 B2
- Document ID: US8771844B2
- Status: Granted
- Kind: B2
- Application number: 13/312,002
- Filed: 2011-12-06
- Published: 2012-12-27
- Granted: 2014-07-08
- Earliest claimed: 2011-06-22
- Assignees: Samsung Display Co., Ltd.
- Applicants: Young-Kook Kim; Seok-Hwan Hwang; Hye-Jin Jung; Jin-O Lim; Sang-Hyun Han; Yoon-Hyun Kwak; Sun-Young Lee; Se-Jin Cho; Jong-Hyuk Lee; Sung-Chul Kim
- Inventors: Young-Kook Kim; Seok-Hwan Hwang; Hye-Jin Jung; Jin-O Lim; Sang-Hyun Han; Yoon-Hyun Kwak; Sun-Young Lee; Se-Jin Cho; Jong-Hyuk Lee; Sung-Chul Kim
- Web page: https://patentgrep.com/patent/US8771844B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 471/22: in which the condensed systems contains four or more hetero rings
- 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 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A heterocyclic compound, an organic light-emitting diode, and a flat display device, the heterocyclic compound being represented by Formula 1, below:

## Claims

### Claim 1

A heterocyclic compound represented by Formula 1 below:
wherein:
A1 and A2 are each independently a substituted or unsubstituted fused pyridine cycle,
R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cyclo alkyl group, a substituted or unsubstituted C3-C30 cyclo alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C3-C30 hetero aryl group, or a group represented by N(Q1)(Q2),
wherein Q1, and Q2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cyclo alkyl group, a substituted or unsubstituted C3-C30 cyclo alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, or a substituted or unsubstituted C3-C30 hetero aryl group,
L1 and L2 are each independently a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group, and
a and b are each independently an integer of 0 to 3.

### Claim 2 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein:
A1 and A2 are each independently a group represented by one of Formulae 2A to 2D, below:
R9 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cyclo alkyl group, a substituted or unsubstituted C3-C30 cyclo alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C3-C30 hetero aryl group, or a group represented by N(Q3)(Q4), in which Q3 and Q4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cyclo alkyl group, a substituted or unsubstituted C3-C30 cyclo alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, or a substituted or unsubstituted C3-C30 hetero aryl group,
p is an integer from 1 to 3, and
* and *′ are sites for fusing.

### Claim 3 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein:
A1 and A2 are each independently a group represented by one of Formulae 3AA to 3BB, below:
and
* and *′ are sites for fusing.

### Claim 4 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted non-phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted phenanthrollinyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorantenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chricenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pycenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted pyrido indolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted phthallazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted puranyl group, a substituted or unsubstituted benzopuranyl group, a substituted or unsubstituted dibenzopuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted isooxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted tetrazolyl group, or a group represented by N(Q1)(Q2),
wherein Q1, and Q2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted pyridinyl group.

### Claim 5 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyrido indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted puranyl group, a substituted or unsubstituted benzopuranyl group, a substituted or unsubstituted dibenzopuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted triazinyl group, or a group represented by N(Q1)(Q2),
wherein Q1, and Q2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted pyridinyl group.

### Claim 6 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein R1 and R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyrido indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted puranyl group, a substituted or unsubstituted benzopuranyl group, a substituted or unsubstituted dibenzopuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted triazinyl group, or a group represented by N(Q1)(Q2),
wherein Q1, and Q2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted pyridinyl group, and
R2, R3, R4, R5, R7, and R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, or a substituted or unsubstituted pentyl.

### Claim 7 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein:
R2, R3, R4, R6, R7, and R8 are hydrogen atoms,
R1 and R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted isobutyl group, or a group represented by one of Formulae 4AA to 4BK below:
Z1, Z2, Z3, Z4, and Z5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, or a substituted or unsubstituted pyridinyl group,
q is an integer of 1 to 5,
r and u are each independently an integer of 1 to 4,
s and x are each independently an integer of 1 to 3,
v is an integer of 1 or 2, and
* represents a binding site.

### Claim 8 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein L1 and L2 are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, or a substituted or unsubstituted oxadiazolylene group.

### Claim 9 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein:
L1 and L2 are each independently a group represented by one of Formulae 5A to 5I, below:
Z6, Z7, and Z8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, or a substituted or unsubstituted phenyl,
r′ and u′ are each independently an integer of 1 to 4,
s′ is an integer of 1 to 3,
v′ and y′ are each independently an integer of 1 to 2, and
* and *′ each represent a binding site.

### Claim 10 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein a and b are each independently an integer of 0 or 1.

### Claim 11 (depends on 1)

The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Formula 1 is represented by one of the following Compounds 7, 10, 21, 24, 25, 31, 41, and 57:

### Claim 12 (depends on 1)

An organic light-emitting diode, comprising:
a first electrode;
a second electrode facing the first electrode; and
a first layer between the first electrode and the second electrode, the first layer including the heterocyclic compound as claimed in claim 1 alone or in a mixed form with other materials.

### Claim 13 (depends on 12)

The organic light-emitting diode as claimed in claim 12, wherein the first layer includes at least one layer selected from the group of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transportation function, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a functional layer having an electron transportation function and an electron injection function.

### Claim 14 (depends on 12)

The organic light-emitting diode as claimed in claim 12, wherein the first layer includes an emission layer, the emission layer including at least one selected from the group of a fluorescent host, a phosphorescent host, a fluorescent dopant, and a phosphorescent dopant.

### Claim 15 (depends on 14)

The organic light-emitting diode as claimed in claim 14, wherein:
the emission layer includes the heterocyclic compound, and
i) the fluorescent host includes the heterocyclic compound,
ii) the fluorescent dopant includes the heterocyclic compound, or
iii) the fluorescent host and the fluorescent dopant each include the heterocyclic compound.

### Claim 16 (depends on 12)

The organic light-emitting diode as claimed in claim 12, wherein the first layer includes an emission layer, the emission layer including at least one selected from the group of an anthracene-based compound, an arylamine-based compound, and a styryl-based compound.

### Claim 17 (depends on 16)

The organic light-emitting diode as claimed in claim 16, wherein the emission layer includes the heterocyclic compound.

### Claim 18 (depends on 12)

The organic light-emitting diode as claimed in claim 12, wherein the first layer includes an electron transport layer, the electron transport layer including the heterocyclic compound.

### Claim 19 (depends on 12)

The organic light-emitting diode as claimed in claim 12, wherein the first layer includes an electron transport layer, the electron transport layer including a metal-containing compound.

### Claim 20 (depends on 19)

The organic light-emitting diode as claimed in claim 19, wherein the metal-containing compound includes a lithium (Li) complex.

### Claim 21 (depends on 12)

The organic light-emitting diode as claimed in claim 12, wherein the first layer includes an emission layer and an electron transport layer, each of the emission layer and the electron transport layer including the heterocyclic compound.

### Claim 22 (depends on 12)

The organic light-emitting diode as claimed in claim 12, wherein the first layer includes at least one layer selected from the group of a hole injection layer, a hole transport layer, and a functional layer having a hole injection function and a hole transportation function, the at least one layer selected from the group of the hole injection layer, the hole transport layer, and the functional layer having a hole injection function and a hole transportation function further including a charge generation material.

### Claim 23 (depends on 12)

A flat display device, comprising:
a transistor including a source, a drain, a gate, and an active layer; and
the organic light-emitting diode as claimed in claim 12,
wherein the source or the drain is electrically connected to the first electrode of the organic light-emitting diode.