# US 11,299,466 B2 · Compound, and organic electronic element comprising same

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- Number: US 11,299,466 B2
- Document ID: US11299466B2
- Status: Granted
- Kind: B2
- Application number: 16/090,681
- Filed: 2017-04-11
- Published: 2020-01-09
- Granted: 2022-04-12
- Earliest claimed: 2016-04-12
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Min Woo Jung; Dong Hoon Lee; Tae Yoon Park; Jungoh Huh; Boonjae Jang; Seongmi Cho; Minyoung Kang; Dong Uk Heo; Miyeon Han; Jungha Lee
- Web page: https://patentgrep.com/patent/US11299466B2

## CPC

- C07D 251/24: to three ring carbon atoms
- C07D 235/06: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 263/57: Aryl or substituted aryl radicals
- C07D 277/66: with aromatic rings or ring systems directly attached in position 2
- C09K 11/06: containing organic luminescent materials
- H10K 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/649: {Aromatic compounds comprising a hetero atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- 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}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- H10K 50/165: comprising dopants
- H10K 50/18: Carrier blocking layers
- H10K 50/181: {Electron blocking layers}
- 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 compound of Chemical Formula 1 and an organic electronic device comprising the same.

## Claims

### Claim 1

A compound represented by the following Chemical Formula 1:
wherein, in Chemical Formula 1,
X is a substituted phenyl group; a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridine group, or a substituted or unsubstituted isoquinoline group;
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
Y is selected from among the following structural formulae;
two or more of Z1 to Z3 are N, and the rest are N or CR;
Ar1 to Ar3 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
R and R1 to R4 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl 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 alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
a is an integer of 5;
b is an integer of 4;
c is an integer of 3;
d is an integer of 4;
a plurality of R1s are the same as or different from each other;
a plurality of R2s are the same as or different from each other;
a plurality of R3s are the same as or different from each other; and
a plurality of R4s are the same as or different from each other,
provided that
when Y is
and X is the substituted phenyl group, then the substituent of the phenyl group for X is not an unsubstituted alkoxy group, an unsubstituted methyl group, an unsubstituted phenyl group, or a group comprising a substituted or unsubstituted arylamine group,
when Y is
and X is the substituted biphenyl group, then the substituent of the biphenyl group for X is not a substituted or unsubstituted arylamine group,
when Y is
and X is the substituted anthracenyl group, then the substituent of the anthracenyl group for X is deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amide group; an alkoxy group; an alkyl group; a cycloalkyl group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an alkenyl group; a silyl group; a boron group; an amine group; a phosphine oxide group; an arylamine group; a phenyl, a naphthyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, an anthracenyl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a perylenyl group, a chrysenyl group, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, or a dibenzofuranyl group, each of which is unsubstituted, and
when Y is
and X is the substituted phenyl group, then the substituent of the phenyl group for X is not a substituted or unsubstituted arylamine group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
and X are different from each other.

### Claim 3 (depends on 1)

The compound of claim 1, wherein L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R and R1 to R4 are hydrogen.

### Claim 6 (depends on 1)

The compound of claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formulae 2 to 4:
wherein Chemical Formulae 2 to 4,
definitions of X, Y, L1, R, R1 to R3 and a to c are the same as in Chemical Formula 1.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Chemical Formula 1 is any one selected from among the following compounds:

### Claim 8 (depends on 1)

An organic electronic device comprising:
a first electrode;
a second electrode provided opposite to the first electrode; and
one or more organic material layers provided between the first electrode and the second electrode,
wherein the one or more organic material layers comprise the compound of claim 1.

### Claim 9 (depends on 8)

The organic electronic device of claim 8, wherein the one or more organic material layers comprise an electron injection layer, an electron transfer layer or a layer carrying out electron injection and electron transfer at the same time, and the electron transfer layer, the electron injection layer or the layer carrying out electron injection and electron transfer at the same time comprises the compound.

### Claim 10 (depends on 8)

The organic electronic device of claim 8, wherein the one or more organic material layers comprise an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound.

### Claim 11 (depends on 8)

The organic electronic device of claim 8, which is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photo conductor (OPC) and an organic transistor.