# US 2014/0197383 A1 · Organic Light-Emitting Diode Comprising Amine-Based Compounds and Anthracene-Based Compounds

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- Number: US 2014/0197383 A1
- Document ID: US20140197383A1
- Status: Published application
- Kind: A1
- Application number: 13/942,641
- Filed: 2013-07-15
- Published: 2014-07-17
- Earliest claimed: 2013-01-11
- Assignees: Samsung Display Co., Ltd.; Seoul National University R&Db Foundation
- Inventors: Hwan-Hee Cho; Mi-Kyung Kim; Se-Hun Kim; Chang-Woong Chu; Myoung-Ki Kim; Jong-In Hong
- Web page: https://patentgrep.com/patent/US20140197383A1

## CPC

- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- C09K 11/06: containing organic luminescent materials
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- C09K 2211/1011: Condensed systems
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/30: Coordination compounds
- 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 anthracene-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 anthracene-based compound may be in the second emission layer.

## Claims

### Claim 1

An organic light-emitting diode comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode and including an emission layer, the organic layer comprising at least one amine-based compound represented by Formula 1 and at least one anthracene-based compound represented by Formula 2:
wherein in Formulas 1 and 2:
X1 and X2 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 and n2 are each independently an integer from 0 to 5, and when n1 is an integer of 2 or more, the 2 or more X1 groups are the same or different, and when n2 is an integer of 2 or more, the 2 or more X2 groups are the same or different;
Y1 and Y2 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-C30 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl 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-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;
Z1 is an electron transporting group and is 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 and R2 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 and a2 are each independently an integer from 0 to 9, and when a1 is an integer of 2 or more, the 2 or more R1 groups are the same or different, and when a2 is an integer of 2 or more, the 2 or more R2 groups are the same or different; and
b1 and b2 are each independently an integer of 1 or 2.

### Claim 2 (depends on 1)

The organic light-emitting diode of claim 1, wherein X1 and X2 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; 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; 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 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 C2-C16 heteroaryl group.

### Claim 3 (depends on 1)

The organic light-emitting diode of claim 1, wherein X1 and X2 are each independently:
i) a phenylene group, a naphthylene group, or an anthracenylene group; or
ii) a phenylene group, a naphthylene group, or an anthracenylene 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 phenylene group, a naphthylene group, or an anthracenylene 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; or
iv) a phenylene group, a naphthylene group, or an anthracenylene 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, 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 pyrrolyl group, an imidazolyl group, pyrazolyl group, a triazolyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a benzoimidazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, or a benzoxazolyl group.

### Claim 4 (depends on 1)

The organic light-emitting diode of claim 1, wherein X1 and X2 are each independently a group represented by Formula 4a:
wherein in Formula 4a:
R41 is 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 integer of 0 to 4, and when d1 is an integer of 2 or more, the 2 or more R41 groups are the same or different;
* is a bonding site to an anthracene ring; and
*′ is a binding site to N or Z.

### Claim 5 (depends on 1)

The organic light-emitting diode of claim 1, wherein n1 and n2 are both 1.

### Claim 6 (depends on 1)

The organic light-emitting diode of claim 1, wherein Y1 and Y2 are each independently:
i) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a furanyl group, a benzofuranyl group, or a dibenzofuranyl group; or
ii) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a furanyl group, a benzofuranyl group, or a dibenzofuranyl 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, 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 or a salt thereof, a phosphoric acid 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 7 (depends on 1)

The organic light-emitting diode of claim 1, wherein Y1 and Y2 are each independently:
i) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a furanyl group, a benzofuranyl group, or a dibenzofuranyl group; or
ii) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a furanyl group, a benzofuranyl group, or a dibenzofuranyl 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, an anthryl group, a fluorenyl group, a furanyl group, a benzofuranyl group, or a dibenzofuranyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group; or
iv) a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a furanyl group, a benzofuranyl group, or a dibenzofuranyl 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 pyrrolyl group, a imidazolyl group, a pyrazolyl group, a triazolyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a benzoimidazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, or a benzoxazolyl group.

### Claim 8 (depends on 1)

The organic light-emitting diode of claim 1, wherein Y1 and Y2 are each independently:
i) a phenyl group, a fluorenyl group, or a dibenzofuranyl group; or
ii) a phenyl group, a fluorenyl group, or a dibenzofuranyl 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, or an iso-butyl group; or
iii) a phenyl group, a fluorenyl group, or a dibenzofuranyl 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 and Y2 are each independently at least one group represented by one of Formulas 5a to 5e:
wherein in Formulas 5a to 5e, * is a bonding site to N.

### Claim 10 (depends on 1)

The organic light-emitting diode of claim 1, wherein Z1 is:
i) a pyrrolyl group, an imidazolyl group, a pyrazolyl 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; or
ii) a pyrrolyl group, an imidazolyl group, a pyrazolyl 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 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; 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 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 11 (depends on 1)

The organic light-emitting diode of claim 1, wherein Z1 is:
i) an oxazolyl group, an isoxazolyl group, or an oxadiazolyl group; or
ii) an oxazolyl group or an isoxazolyl 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) an oxazolyl group or an isoxazolyl 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) an oxazolyl group or an isoxazolyl 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 substituted with 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, 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 is at least one group represented by one of Formulas 3a to 3e:
wherein, in Formulas 3a to 3e:
R31 to R35 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 and c2 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, and when c2 is an integer of 2 or more, the 2 or more R32 groups are the same or different; and
* is a bonding site to X2.

### Claim 13 (depends on 1)

The organic light-emitting diode of claim 1, wherein R1 and R2 are each independently a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, and 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 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 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 anthracene-based compound is represented by Formula 2a:
wherein in Formula 1a:
X1 is a phenylene group; or a phenylene 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, or a phenyl group; and
Y1 and Y2 are each independently:
i) a phenyl group, a fluorenyl group, or a dibenzofuranyl group;
ii) a phenyl group, a fluorenyl group, or a dibenzofuranyl 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;
iii) a phenyl group, a fluorenyl group, or a dibenzofuranyl 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, or a nitro group; or
iv) a phenyl group, a fluorenyl group, or a dibenzofuranyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a fluorenyl group, and
wherein in Formula 2a:
X2 is a phenylene group; or a phenylene 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, or a phenyl group; and
Z1 is at least one group represented by one of Formulas 3a to 3e:
wherein in Formulas 3a to 3e:
R31 to R35 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 and c2 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, and when c2 is an integer of 2 or more, the 2 or more R32 groups are the same or different; and
* is a bonding site to X2.

### Claim 15 (depends on 1)

The organic light-emitting diode of claim 1, wherein the amine-based compound is one of Compounds 1 to 5, and the anthracene-based compound is one of Compounds 6 to 11:

### 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 further comprising 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 further comprising at least one of an electron transport layer, and an electron injection layer.

### Claim 17 (depends on 1)

The organic light-emitting diode of claim 1, wherein the amine-based compound and the anthracene-based compound are included in the emission layer.

### Claim 18 (depends on 17)

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

### Claim 19 (depends on 17)

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