# US 11,306,060 B2 · Compound and organic electronic element comprising same

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- Number: US 11,306,060 B2
- Document ID: US11306060B2
- Status: Granted
- Kind: B2
- Application number: 16/085,547
- Filed: 2017-09-08
- Published: 2019-05-23
- Granted: 2022-04-19
- Earliest claimed: 2016-09-09
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Yongbum Cha; Sang Duk Suh; Jungbum Kim; Sung Kil Hong
- Web page: https://patentgrep.com/patent/US11306060B2

## CPC

- C07D 221/20: Spiro-condensed ring systems
- C07C 211/54: having amino groups bound to two or three six-membered aromatic rings
- C07D 219/02: with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 471/06: Peri-condensed systems
- C07D 471/10: Spiro-condensed systems
- C07F 7/0812: {comprising a heterocyclic ring}
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/171: {Electron injection layers}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- 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 85/657: {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 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- H10K 50/15: Hole transporting layers
- H10K 50/181: {Electron blocking layers}
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present specification relates to a compound and an organic electronic device comprising the same.

## Claims

### Claim 1

A compound represented by one of the following Chemical Formulae 2 to 8:
wherein, in Chemical Formulae 2 to 8,
R1 to R25 are hydrogen,
L101 and L102 are each independently a direct bond,
L1 to L4 are the same as or different from each other, and each independently a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a fluorenylene group; a divalent carbazole group; a divalent dibenzofuran group; or a divalent dibenzothiophene group, and
Ar1 to Ar4 are the same as or different from each other, and each independently a methyl group; an ethyl group; a tert-butyl group; a cyclopentyl group; a cyclohexyl group; a phenyl group unsubstituted or substituted with fluorine, a trimethylsilyl group, a nitrile group, trifluoromethyl group, or a methyl group; a biphenyl group; a naphthyl group; an N-phenyl carbazole group; or a dibenzofuran group unsubstituted or substituted with fluorine, a trimethylsilyl group, a nitrile group, trifluoromethyl group, or a methyl group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein any one or more of Ar1 and Ar2 are the following Chemical Formula 1A:
wherein, in Chemical Formula 1A,
X is O or NR,
R is a phenyl group; and R26 to R29 are hydrogen; with the proviso that when X is NR,
R26 to R29 are the same as or different from each other, and each independently hydrogen; fluorine; a nitrile group; a methyl group; a trifluoromethyl group; a trimethylsilyl group; with the proviso that when X is O, and
any one of R30 to R33 bonds to L1 or L2 of Chemical Formulae 2 to 8, and groups that do not bond to L1 or L2 of Chemical Formulae 2 to 8 among R30 to R33 are hydrogen.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

An organic electronic 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 one or more layers of the organic material layer comprise the compound of claim 1.

### Claim 5 (depends on 4)

The organic electronic device of claim 4, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound.

### Claim 6 (depends on 4)

The organic electronic device of claim 4, wherein the organic material layer comprises an electron injection layer, and the electron injection layer comprises the compound.

### Claim 7 (depends on 4)

The organic electronic device of claim 4, wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the compound.

### Claim 8 (depends on 4)

The organic electronic device of claim 4, wherein the organic material layer comprises a hole injection layer, a hole transfer layer, or a layer carrying out hole injection and transfer at the same time, and the hole injection layer, the hole transfer layer, or the layer carrying out hole injection and transfer at the same time comprises the compound.

### Claim 9 (depends on 4)

The organic electronic device of claim 4, further comprising one, two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer and an electron blocking layer.

### Claim 10 (depends on 4)

The organic electronic device of claim 4, 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.

### Claim 11

An organic electronic 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 one or more layers of the organic material layer comprise a compound represented by the following Chemical Formula 1,
wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound as a dopant material and comprises a compound represented by the following Chemical Formula 9 as a host material:
in Chemical Formula 1,
at least one of R1 to R25 is
L101, L1, and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group;
Ar1 and Ar2 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 silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
groups that are not
among R1 to R25 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bond to adjacent groups to form a substituted or unsubstituted ring; and
means a site bonding to other substituents or bonding sites,
in Chemical Formula 9,
Y is O or S,
G11 is a substituted or unsubstituted aryl group,
G12 to G15 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; 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 phosphine oxide group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
g12, g13 and g15 are each an integer of 1 to 4,
g14 is an integer of 1 to 3, and
when g12 to g15 are each 2 or greater, the two or more G12s to G15s are each the same as or different from each other.

### Claim 12 (depends on 11)

The organic electronic device of claim 11, wherein the compound represented by Chemical Formula 9 is any one selected from the following compounds: