# US 2014/0197381 A1 · Organic light-emitting diode comprising amine-based compounds and pyrene-based compounds

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- Number: US 2014/0197381 A1
- Document ID: US20140197381A1
- Status: Published application
- Kind: A1
- Application number: 13/940,195
- Filed: 2013-07-11
- Published: 2014-07-17
- Earliest claimed: 2013-01-11
- Assignees: Samsung Display Co., Ltd.; Seoul National University R&Db Foundation
- Inventors: Se-Hun Kim; Hwan-Hee Cho; Myoung-Ki Kim; Mi-Kyung Kim; Chang-Woong Chu; Jong-In Hong
- Web page: https://patentgrep.com/patent/US20140197381A1

## CPC

- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- C09K 11/06: containing organic luminescent materials
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/6565: {Oxadiazole compounds}
- C09K 2211/188: of other metals not provided for in one of the previous groups
- H10K 50/125: specially adapted for multicolour light emission, e.g. for emitting white light
- H10K 50/13: comprising stacked EL layers within one EL unit
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

An organic light-emitting diode includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode. The organic layer includes an emission layer. The organic layer also includes at least one amine-based compound and at least one pyrene-based compound. The organic layer may include a first emission layer and a second emission layer, and the amine-based compound may be in the first emission layer and the pyrene-based compound may be in the second emission layer.

## 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, wherein the organic layer comprises an emission layer comprising at least one amine-based compound represented by Formula 1 and at least one pyrene-based compound represented by Formula 2:
wherein, in Formula 1 and 2:
X1 to X4 are each independently a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 heteroarylene group;
n1 to n4 are each independently an integer of 0 to 5, and when n1 is an integer of 2 or more, the 2 or more X1 groups are the same or different, when n2 is an integer of 2 or more, the 2 or more X2 groups are the same or different, when n3 is an integer of 2 or more, the 2 or more X3 groups are the same or different, and when n4 is an integer of 2 or more, the 2 or more X4 groups are the same or different;
Y1 to Y4 are each independently a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;
Z1 and Z2 are each independently an electron transporting group and are each independently a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, or a substituted or unsubstituted C2-C60 heteroaryl group;
R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, or a substituted or unsubstituted C2-C60 heteroaryl group;
a1 to a4 are each independently an integer of 0 to 4, and when a1 is an integer of 2 or more, the 2 or more R1 groups are the same or different, when a2 is an integer of 2 or more, the 2 or more R2 groups are the same or different, when a3 is an integer of 2 or more, the 2 or more R3 groups are the same or different, and when a4 is an integer of 2 or more, the 2 or more R4 groups are the same or different; and
b1 and b2 are each independently an integer of 0 or 1.

### Claim 2 (depends on 1)

The organic light-emitting diode of claim 1, wherein X1 to X4 are each independently:
i) a phenylene group, a naphthylene group, an anthracenylene group, or a fluorenylene group; or
ii) a phenylene group, a naphthylene group, an anthracenylene group, or a fluorenylene group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a C1-C10 alkyl group; or
a C6-C16 aryl group or a C2-C16 heteroaryl group; or
a C6-C16 aryl group or a C2-C16 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C6-C16 aryl group, or a C2-C16 heteroaryl group.

### Claim 3 (depends on 3)

The organic light-emitting device of claim 3, wherein X1 to X4 are each independently:
i) a phenylene group or a naphthylene group; or
ii) a phenylene group or a naphthylene group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; an n-butyl group, an iso-butyl group, or a tert-butyl group; or
iii) a phenylene group or a naphthylene group substituted with at least one of a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; an n-butyl group, an iso-butyl group, or a tert-butyl group;
iv) a phenylene group or a naphthylene group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group; or
v) a phenylene group or a naphthylene group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, and a fluorenyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, a pyrrolyl group, an imidazolyl group, a triazolyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a benzoimidazolyl group, an oxazolyl group, an isooxazolyl group, an oxadiazolyl group, or a benzoxazolyl group.

### Claim 4 (depends on 1)

The organic light-emitting diode of claim 1, wherein X1 to X4 are each independently at least one group represented by one of Formulas 4a to 4d:
wherein, in Formulas 4a to 4d:
R41 to R44 are each independently a hydrogen atom, a deuterium atom, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group;
d1 is an integer of 0 to 4, and when d1 is a integer of 2 or more, the 2 or more R41 groups are the same or different;
d2 to d4 are each independently an integer of 0 to 6, and when d2 is an integer of 2 or more, the 2 or more R42 groups are the same or different, when d3 is an integer of 2 or more, the 2 or more R43 groups are the same or different, and when d4 is an integer of 2 or more, the 2 or more R44 groups are the same or different;
* is a bonding site to a pyrene ring; and
*′ is a bonding site to N, Z1 or Z2.

### Claim 5 (depends on 1)

The organic light-emitting diode of claim 1, wherein n1 to n4 are each 1.

### Claim 6 (depends on 1)

The organic light-emitting diode of claim 1, wherein Y1 to Y4 are each independently:
i) a phenyl group, a naphthyl group, an anthryl group, or a fluorenyl group; or
ii) a phenyl group, a naphthyl group, an anthryl group or a fluorenyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, or a C1-C10 alkyl group; or
a C1-C10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid or a salt thereof, or a phosphoric acid or a salt thereof; or
a C6-C16 aryl group or a C2-C16 heteroaryl group; or
a C6-C16 aryl group or a C2-C16 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a C6-C16 aryl group, or a C2-C16 heteroaryl group.

### Claim 7 (depends on 1)

The organic light-emitting device of claim 1, wherein Y1 to Y4 are each independently:
i) a phenyl group, a naphthyl group, or a fluorenyl group; or
ii) a phenyl group, a naphthyl group, or a fluorenyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; or
iii) a phenyl group, a naphthyl group, or a fluorenyl group substituted with a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group; or
iv) a phenyl group, a naphthyl group, or a fluorenyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group.

### Claim 8 (depends on 1)

The organic light-emitting diode of claim 1, wherein Y1 to Y4 are each independently:
i) a phenyl group, a naphthyl group, or a fluorenyl group; or
ii) a phenyl group, a naphthyl group, or a fluorenyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; or
iii) a phenyl group, naphthyl group, or a fluorenyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group.

### Claim 9 (depends on 1)

The organic light-emitting diode of claim 1, wherein Y1 to Y4 are each independently at least one group represented by one of Formulas 5a to 5f:
wherein, in Formulas 5a to 5f:
* is a bonding site to N, Z1 or Z2.

### Claim 10 (depends on 1)

The organic light-emitting diode of claim 1, wherein Z1 and Z2 are each independently:
i) a pyrrolyl group, an imidazolyl group, a triazolyl group, a pyridyl group, a triazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a benzoimidazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, or a benzoxazolyl group; or
ii) a pyrrolyl group, an imidazolyl group, a triazolyl group, a pyridyl group, a triazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a benzoimidazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, or a benzoxazolyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof, or a C1-C10 alkyl group; a C1-C10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof; a C6-C16 aryl group or a C2-C16 heteroaryl group; or a C6-C16 aryl group or a C2-C16 heteroaryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C6-C16 aryl group, or a C2-C16 heteroaryl group.

### Claim 11 (depends on 1)

The organic light-emitting diode of claim 1, wherein Z1 and Z2 are each independently:
i) a triazolyl group, a pyridyl group, a triazinyl group, a benzoimidazolyl group, or an oxadiazolyl group; or
ii) a triazolyl group, a pyridyl group, a triazinyl group, a benzoimidazolyl group, or an oxadiazolyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; or
iii) a triazolyl group, a pyridyl group, a triazinyl group, a benzoimidazolyl group, or an oxadiazolyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, or a triazolyl group; or
iv) a triazolyl group, a pyridyl group, a triazinyl group, a benzoimidazolyl group, and an oxadiazolyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, and a triazolyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, or an anthracenyl group.

### Claim 12 (depends on 1)

The organic light-emitting diode of claim 1, wherein Z1 and Z2 are each independently a group represented by one of Formulas 3a to 3i:
wherein, in Formulas 3a to 3i:
R31 to R39 are each independently a hydrogen atom, a deuterium atom, —F, a cyano group, a methyl group, an ethyl group, a phenyl group, a biphenyl group, or a naphthyl group;
c1 to c5 are each independently an integer of 0 to 4, and when c1 is an integer of 2 or more, the 2 or more R31 groups are the same or different, when c2 is an integer of 2 or more, the 2 or more R32 groups are the same or different, when c3 is an integer of 2 or more, the 2 or more R33 groups are the same or different, when c4 is an integer of 2 or more, the 2 or more R34 groups are the same or different, and when c5 is an integer of 2 or more, the 2 or more R35 groups are the same or different;
c6 to c8 are each independently an integer of 0 to 3, and when c6 is an integer of 2 or more, the 2 or more R36 groups are the same or different, when c7 is an integer of 2 or more, the 2 or more R37 groups are the same or different, and when c8 is an integer of 2 or more, the 2 or more R38 groups are the same or different; and
* is a bonding site to X3 or X4.

### Claim 13 (depends on 1)

The organic light-emitting diode of claim 1, wherein R1 to R4 are each independently:
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, or a C1-C10 alkyl group; or
a C1-C10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a phosphoric acid group or a salt thereof; or
a C6-C16 aryl group; or
a C6-C16 aryl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, or an anthryl group.

### Claim 14 (depends on 1)

The organic light-emitting diode of claim 1, wherein the amine-based compound is represented by Formula 1a and the pyrene-based compound is represented by Formula 2a:
wherein, in Formula 1a:
X1 is a phenylene group or a naphthylene group; or a phenylene group or a naphthylene group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; and
Y1 and Y2 are each independently:
i) a phenyl group, a naphthyl group, or a fluorenyl group; or
ii) a phenyl group, a naphthyl group, or a fluorenyl group substituted with at least one of a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; or
iii) a phenyl group, a naphthyl group, or a fluorenyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group;
wherein, in Formula 2a:
X3 is a phenylene group or a naphthylene group; or a phenylene group or a naphthylene group substituted with at least one of a deuterium atom ion, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, or a tert-butyl group; or
Z1 and Z2 are each independently at least one group represented by one of Formulas 3a to 3i:
wherein, in Formulas 3a to 3i:
R31 to R39 are each independently a hydrogen atom, a deuterium atom, —F, a cyano group, a methyl group, an ethyl group, a phenyl group, a biphenyl group, or a naphthyl group;
c1 to c5 are each independently an integer of 0 to 4, and when c1 is an integer of 2 or more, the 2 or more R31 groups are the same or different, when c2 is an integer of 2 or more, the 2 or more R32 groups are the same or different, when c3 is an integer of 2 or more, the 2 or more R33 groups are the same or different, when c4 is an integer of 2 or more, the 2 or more R34 groups are the same or different, and when c5 is an integer of 2 or more, the 2 or more R35 groups are the same or different;
c6 to c8 are each independently an integer of 0 to 3, and when c6 is an integer of 2 or more, the 2 or more R36 groups are the same or different, when c7 is an integer of 2 or more, the 2 or more R37 groups are the same or different, and when c8 is an integer of 2 or more, the 2 or more R38 groups are the same or different; and
* is a bonding site to X3 or X4.

### Claim 15 (depends on 1)

The organic light-emitting diode of claim 1, wherein the amine-based compound is at least one of compounds 1 to 14, and the pyrene-based compound is at least one of compounds 15 to 21:

### Claim 16 (depends on 1)

The organic light-emitting diode of claim 1, wherein the organic layer comprises:
a hole transport region between the first electrode and the emission layer and having at least one of a hole injection layer, a hole transport layer, a functional layer having both hole injection ability and hole transport ability, a buffer layer, and/or an electron blocking layer; and
an electron transport region between the emission layer and the second electrode and having at least one of a hole blocking layer, an electron transport layer, and/or an electron injection layer.

### Claim 17 (depends on 1)

The organic light-emitting diode of claim 1, wherein the emission layer comprises the amine-based compound and the pyrene-based compound.

### Claim 18 (depends on 17)

The organic light-emitting diode of claim 17, wherein the amine-based compound and the pyrene-based compound are co-deposited.

### Claim 19 (depends on 17)

The organic light-emitting diode of claim 17, wherein the emission layer comprises a first emission layer and a second emission layer, and the first emission layer comprises the amine-based compound, and the second emission layer comprises the pyrene-based compound.

### Claim 20 (depends on 19)

The organic light-emitting diode of claim 19, wherein the first emission layer is between the second emission layer and the first electrode.