# US 12,010,915 B2 · Organic light-emitting diode having long lifespan, low voltage, and high efficiency property

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,010,915 B2
- Document ID: US12010915B2
- Status: Granted
- Kind: B2
- Application number: 16/338,717
- Filed: 2017-09-14
- Published: 2021-09-16
- Granted: 2024-06-11
- Earliest claimed: 2016-10-05
- Assignees: Sfc Co., Ltd.
- Applicants: Sfc Co., Ltd.
- Inventors: Soon-Wook Cha; Sang-Woo Park; Jung-Ho Yoo; Ji-Hwan Kim; Sung Woo Kim; Hyeon Jun Jo; Young-Hwan Park
- Web page: https://patentgrep.com/patent/US12010915B2

## CPC

- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/10: linked by a carbon chain containing aromatic rings
- C07D 409/14: containing three or more hetero rings
- C09K 11/06: containing organic luminescent materials
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07C 2603/40: containing four condensed rings
- C07C 2603/52: containing five condensed rings
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1018: Heterocyclic compounds
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/623: {containing five rings, e.g. pentacene}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present disclosure relates to an organic light-emitting diode and, more particularly, to an organic-light-emitting diode comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer intercalated between the first electrode and the second electrode, wherein the light-emitting layer comprises at least one of the amine compounds represented by the following Chemical Formula A and at least one of the anthracene compounds represented by the following Chemical Formula B or C. The structures of Chemical Formulas A to C are the same as in the specification.

## Claims

### Claim 1

An organic light-emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer intercalated between the first electrode and the second electrode,
wherein the light-emitting layer comprises at least one of the amine compounds represented by the following Chemical Formula A and at least one of the anthracene compounds represented by the following Chemical Formula B:
wherein,
Z3 is a substituted or unsubstituted aromatic hydrocarbon ring, selected from between Structural Formula 11 and Structural Formula 15:
wherein
“-*” denotes a bonding site for forming a 5-membered ring containing the carbon atom connected to both R14 and R15,
R's are as defined below for R16 to R19, and
m is an integer of 1 to 8 wherein when m is 2 or more or when R is two or more, individual R's are same or different,
the substituents R14 and R15, which are the same or different, are each independently one selected from among a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, and a substituted or unsubstituted aryl of 6 to 50 carbon atoms,
R16 to R19, which are the same or different, are each independently one selected from among a hydrogen atom, a deuterium atom, with a proviso that one of the substituents R16 to R19 represents a single bond attached to the linker L in a Q moiety,
two adjacent carbon atoms within Z3 form a five-membered ring with the carbon atom having both the substituents R14 and R15 thereon, thus establishing a fused ring,
a carbon atom of the aromatic ring of Z3 which does not participate in forming the five-membered ring is bonded to the linker L in a Q moiety,
the linker L represents a single bond,
n is an integer of 1,
the respective moieties Q's which are bonded to Z3 and to one of R16 to R19 are same or different,
the substituents Ar1 and Ar2, which are same or different, are each independently one selected from among a substituted or unsubstituted aryl of 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms;
wherein,
R21 to R28, which are same or different, are each independently one selected from among a hydrogen atom, and a deuterium atom,
R31 to R37, which are same or different, are each independently one selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, and
the substituent Ar3 is a deuterium substituted or unsubstituted naphthyl or a substituent represented by the following Structural Formula C:
wherein R41 to R45 are same or different and are a hydrogen atom, a deuterium atom, or a deuterium substituted or unsubstituted aryl of 6 to 50 carbon atoms, or a deuterium substituted or unsubstituted alkyl of 1 to 30 carbon atoms,
wherein the term ‘substituted’ in the expression ‘substituted or unsubstituted’ means having at least one substituent selected from the group consisting of a deuterium, a halogen, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms and an alkylsilyl of 1 to 24 carbon atoms.

### Claim 2 (depends on 1)

The organic light-emitting diode of claim 1, wherein the light emitting-layer comprises a host and a dopant,
wherein the anthracene compound represented by Chemical Formula B is used as the host and the amine compound represented by Chemical Formula A is used as the dopant.

### Claim 3 (depends on 1)

The organic light-emitting diode of claim 1, wherein R14 and R15 are same or different and are each independently a substituted or unsubstituted aryl of 6 to 30 carbon atoms.

### Claim 4 (depends on 1)

The organic light-emitting diode of claim 1, wherein Ar1 and Ar2 are same or different and are each independently a substituted or unsubstituted aryl of 6 to 30 carbon atoms.

### Claim 5 (depends on 1)

The organic light-emitting diode of claim 1, wherein the anthracene compound represented by Chemical Formula B is one selected from among the following Compounds:

### Claim 6 (depends on 1)

The organic light-emitting diode of claim 1, wherein the amine compound represented by Chemical Formula A is one selected from among the following Chemical Formulas:

### Claim 7 (depends on 1)

The organic light-emitting diode of claim 1, further comprising at least one of a hole injection layer, a hole transport layer, a functional layer capable of both hole injection and hole transport, an electron transport layer, and an electron injection layer in addition to the light-emitting layer.

### Claim 8 (depends on 7)

The organic light-emitting diode of claim 7, wherein at least one selected from among the layers is deposited using a deposition process or a solution process.

### Claim 9 (depends on 1)

The organic light-emitting diode of claim 1, wherein the organic light-emitting diode is used for a device selected from among a flat display device, a flexible display device, a monochrome or grayscale flat illumination device, and a monochrome or grayscale flexible illumination device.