# US 10,121,973 B2 · Compound for organic optoelectronic device, organic light-emitting diode including same, and display device including organic light-emitting diode

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- Number: US 10,121,973 B2
- Document ID: US10121973B2
- Status: Granted
- Kind: B2
- Application number: 15/704,102
- Filed: 2017-09-14
- Published: 2018-01-04
- Granted: 2018-11-06
- Earliest claimed: 2011-12-30
- Assignees: Cheil Industries Inc.
- Applicants: Cheil Industries, Inc.
- Inventors: Jin-Seok Hong; Young-Kyoung Jo; Dong-Wan Ryu; Nam-Heon Lee; Han-Ill Lee; Sung-Hyun Jung; Mi-Young Chae; Dal-Ho Huh
- Web page: https://patentgrep.com/patent/US10121973B2

## CPC

- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- 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 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/14: Carrier transporting layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- H10K 50/18: Carrier blocking layers
- H10K 85/623: {containing five rings, e.g. pentacene}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Disclosed are a compound for an organic optoelectronic device, an organic light emitting diode including the same, and a display device including the organic light emitting diode. The compound for an organic optoelectronic device represented by a combination of the following Chemical Formula 1 and Chemical Formula 2 provides an organic light emitting diode having life-span characteristics due to excellent electrochemical and thermal stability, and high luminous efficiency at a low driving voltage.

## Claims

### Claim 1

A compound for an organic optoelectronic device represented by a combination of the following Chemical Formula 1 and Chemical Formula 2:
wherein, in the above Chemical Formulae 1 and 2,
X is —O—, —S—,
Ar1 to Ar4 are independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
L1 and L2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
m1 and m2 are independently integers of 0 or 1, one of m1 and m2 is 1,
n1 and n2 are independently integers ranging from 0 to 1,
R1 to R7 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and
two *s of the above Chemical Formula 2 are bonded with the adjacent two *s of the above Chemical Formula 1 to form a fused ring.

### Claim 2 (depends on 1)

The compound for an organic optoelectronic device of claim 1, wherein the above Chemical Formula 1 is represented by the following Chemical Formula 3:
wherein, in the above Chemical Formula 3,
Ar3 and Ar4 are independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
L2 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
m2 is 1,
n2 is an integer ranging from 0 to 1,
R1 to R3, R6 or R7 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and
two *s of the above Chemical Formula 2 are bonded with the adjacent two *s of the above Chemical Formula 3 to form a fused ring.

### Claim 3 (depends on 1)

The compound for an organic optoelectronic device of claim 1, wherein the compound for an organic optoelectronic device is represented by the following Chemical Formula 4:
wherein, in the above Chemical Formula 4,
X is —O—, —S—, —S(O)—, or —S(O)2—,
Ar1 to Ar4 are independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
L1 and L2 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
m1 and m2 are independently integers of 0 or 1, one of m1 and m2 is 1,
n1 and n2 are independently integers ranging from 0 to 1, and
R1 to R7 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

### Claim 4 (depends on 1)

The compound for an organic optoelectronic device of claim 1, wherein the compound for an organic optoelectronic device is represented by the following Chemical Formula 5:
wherein, in the above Chemical Formula 5,
Ar3 and Ar4 are independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
L2 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
m2 is 1,
n2 is an integer ranging from 0 to 1, and
R1 to R7 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

### Claim 5 (depends on 1)

The compound for an organic optoelectronic device of claim 1, wherein the Ar1 to Ar4 are independently substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiopheneyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiopheneyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, or a combination thereof.

### Claim 6 (depends on 1)

The compound for an organic optoelectronic device of claim 1, wherein the compound for an organic optoelectronic device has triplet exciton energy (T1) of greater than or equal to about 2.0 eV.

### Claim 7 (depends on 1)

The compound for an organic optoelectronic device of claim 1, wherein the organic optoelectronic device is organic optoelectronic device is selected from an organic photoelectric device, an organic light emitting diode.

### Claim 8 (depends on 1)

An organic light emitting diode, comprising
an anode, a cathode, and at least one organic thin layer interposed between the anode and cathode,
wherein at least one of the organic thin layers comprises the above compound for an organic optoelectronic device of claim 1.

### Claim 9 (depends on 8)

The organic light emitting diode of claim 8, wherein the organic thin layer is selected from an emission layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a combination thereof.

### Claim 10 (depends on 9)

The organic light emitting diode of claim 9, wherein the compound for an organic optoelectronic device is included in a hole transport layer (HTL) or a hole injection layer (HIL).

### Claim 11 (depends on 9)

The organic light emitting diode of claim 9, wherein the compound for an organic optoelectronic device is included in an emission layer.

### Claim 12 (depends on 11)

The organic light emitting diode of claim 11, wherein the compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in an emission layer.

### Claim 13 (depends on 8)

The organic light emitting diode as claimed in claim 8, wherein the compound for an organic optoelectronic device is represented by one of the following Chemical Formulae A-1 to A-72:

### Claim 14 (depends on 8)

The organic light emitting diode as claimed in claim 8, wherein the compound for an organic optoelectronic device is represented by one of the following Chemical Formulae B-1 to B-40:

### Claim 15 (depends on 8)

A display device comprising the above organic light emitting diode of claim 8.