# US 10,873,035 B2 · Heterocyclic compound and organic light emitting diode containing same

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

- Number: US 10,873,035 B2
- Document ID: US10873035B2
- Status: Granted
- Kind: B2
- Application number: 15/761,657
- Filed: 2017-02-23
- Published: 2018-12-06
- Granted: 2020-12-22
- Earliest claimed: 2016-02-23
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Yongbum Cha; Seongmi Cho; Jungbum Kim; Sung Kil Hong; Jiwon Kwak
- Web page: https://patentgrep.com/patent/US10873035B2

## CPC

- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 307/93: condensed with a ring other than six-membered
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 407/04: directly linked by a ring-member-to-ring-member bond
- C07D 407/12: linked by a chain containing hetero atoms as chain links
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C09K 11/06: containing organic luminescent materials
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/622: {containing four rings, e.g. pyrene}
- 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 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1088: containing oxygen as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/181: {Electron blocking layers}
- H10K 71/164: {using vacuum deposition}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 2101/10: Triplet emission
- H10K 2102/351: {Thickness}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present specification relates to a hetero-cyclic compound and an organic light emitting device including the same.

## Claims

### Claim 1

A hetero-cyclic compound represented by the following Chemical Formula 1:
in Chemical Formula 1,
R1 to R3 and R5 are the same as or different from each other, and are each independently hydrogen; deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
R4 is hydrogen; deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; an unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, wherein the arylene group in L1 is not an anthracenylene group,
Ar1 is a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, wherein the aryl group in Ar1 is not an anthracenyl group,
r1 and r2 are each an integer from 1 to 5,
r3 is an integer from 1 to 4,
r4 is 1 or 2,
r5 is an integer from 1 to 3, and
when r1 to r5 are each present in a plural number, a plurality of structures in the parenthesis is the same as or different from each other.

### Claim 2 (depends on 1)

The hetero-cyclic compound of claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulae 2 to 5:
in Chemical Formulae 2 to 5,
the definitions of R1 to R5, r1 to r5, L1, and Ar1 are the same as those in Chemical Formula 1.

### Claim 3 (depends on 1)

The hetero-cyclic compound of claim 1, wherein L1 is a direct bond; an unsubstituted arylene group; or an unsubstituted heteroarylene group.

### Claim 4 (depends on 1)

The hetero-cyclic compound of claim 1, wherein Ar1 is an arylamine group which is unsubstituted or substituted with an alkyl group or a heteroaryl group; an N-arylheteroarylamine group which is unsubstituted or substituted with an aryl group; a phosphine oxide group which is substituted with an aryl group; an aryl group which is unsubstituted or substituted with an alkyl group or an aryl group; or a heteroaryl group which is unsubstituted or substituted with an aryl group.

### Claim 5 (depends on 1)

An organic light emitting device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein the one or more layers of the organic material layer comprise the hetero-cyclic compound of claim 1.

### Claim 6 (depends on 5)

The organic light emitting device of claim 5, wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the hetero-cyclic compound.

### Claim 7 (depends on 5)

The organic light emitting device of claim 5, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the hetero-cyclic compound.

### Claim 8 (depends on 5)

The organic light emitting device of claim 5, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the hetero-cyclic compound as a host of the light emitting layer.

### Claim 9 (depends on 5)

The organic light emitting device of claim 5, wherein the organic material layer comprises an electron transporting layer, and the electron transporting layer comprises the hetero-cyclic compound.

### Claim 10

An organic light emitting device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein the organic material layer comprises at least one of a hole transporting layer, an electron blocking layer, or an electron transporting layer, and the at least one of the hole transporting layer the electron blocking layer, or the electron transporting layer comprises a hetero-cyclic compound represented by the following Chemical Formula 1:
in Chemical Formula 1,
R1 to R5 are the same as or different from each other, and are each independently hydrogen;
deuterium; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar1 is a substituted or unsubstituted amine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
r1 and r2 are each an integer from 1 to 5,
r3 is an integer from 1 to 4,
r4 is 1 or 2,
r5 is an integer from 1 to 3, and
when r1 to r5 are each present in a plural number, a plurality of structures in the parenthesis is the same as or different from each other.

### Claim 11

A hetero-cyclic compound selected from the following compounds:

### Claim 12 (depends on 5)

The organic light emitting device of claim 5, wherein the organic material layer comprises a hole transporting layer, and the hole transporting layer comprises the hetero-cyclic compound.

### Claim 13 (depends on 10)

The organic light emitting device of claim 10, wherein the organic material layer comprises a hole transporting layer, and the hole transporting layer comprises the hetero-cyclic compound.

### Claim 14 (depends on 10)

The organic light emitting device of claim 10, wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the hetero-cyclic compound.

### Claim 15 (depends on 10)

The organic light emitting device of claim 10, wherein the organic material layer comprises an electron transporting layer, and the electron transporting layer comprises the hetero-cyclic compound.