# US 10,319,923 B2 · Compound for organic electronic element, organic electronic element comprising the same and electronic device thereof

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

- Number: US 10,319,923 B2
- Document ID: US10319923B2
- Status: Granted
- Kind: B2
- Application number: 15/977,344
- Filed: 2018-05-11
- Published: 2018-10-04
- Granted: 2019-06-11
- Earliest claimed: 2014-10-06
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Bumsung Lee; Sun-hee Lee; Daesung Kim; Yun Suk Lee; Gyumin Lee
- Web page: https://patentgrep.com/patent/US10319923B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 209/82: Carbazoles; Hydrogenated carbazoles
- C07D 409/14: containing three or more hetero rings
- H10K 50/171: {Electron injection layers}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 77/10: Substrates, e.g. flexible substrates
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Provided are a compound of Formula 1 and an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and electronic device comprising the organic electric element, wherein the luminous efficiency and life span can be improved and the driving voltage of the organic electronic device can be lowered by comprising the compound represented by Formula 1 in the organic material layer.

## Claims

### Claim 1

A compound of Formula 1:
wherein
A and B are each independently Formula 1-2 or Formula 1-3, with the proviso that the case where A and B are simultaneously Formula 1-3 is excluded:
Ar1 and Ar4 are each independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; -L′-N(Ra)(Rb); and a combination thereof,
L2 and L3 are each independently selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and the combination thereof,
R1 to R16 are each independently i) selected from the group consisting of hydrogen; deuterium; halogen; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; a C6-C30 aryloxy group; -L′-N(Ra)(Rb); and the combination thereof, or ii) neighboring groups of R1s to R16s may be linked to each other to form a ring together with a benzene ring to which they are bonded, and wherein R1s to R16s not forming a ring are each the same as defined in the above i),
L′ is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P,
Ra and Rb are each independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring; and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and
the above aryl group, fluorenyl group, heterocyclic group, fused ring, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group and fluorenylene group may be each substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C1-C20 alkylthio group; a C1-C20 alkoxy group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C6-C20 aryl group; a C6-C20 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a C3-C20 cycloalkyl group; a C7-C20 arylalkyl group; and a C8-C20 arylalkenyl group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Formula 1 is represented by one of Formulas 6, 7, and 9 below:
wherein Ar1 and Ar4, L2 and L3 and R1 to R16 are each the same as defined in claim 1.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Formula 1 is any one of the compounds below:

### Claim 4 (depends on 1)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of claim 1.

### Claim 5 (depends on 4)

The organic electric element of claim 4, wherein at least one of a hole injection layer, a hole transport layer, an emission-auxiliary layer and an light emitting layer of the organic material layer comprises one kind or two or more kinds of compounds represented by Formula 1.

### Claim 6 (depends on 4)

The organic electric element of claim 4, wherein the organic electric element further including at least one layer to improve luminous efficiency which is formed on at least one of the sides the first and second electrodes, which is opposite to the organic material layer.

### Claim 7 (depends on 4)

The organic electric element of claim 4, wherein the organic material layer is formed by any one of the processes of spin coating, nozzle printing, inkjet printing, slot coating, dip coating and roll-to-roll.

### Claim 8 (depends on 1)

An electronic device comprising:
a display device comprising the organic electric element of claim 1; and
a control unit for driving the display device.

### Claim 9 (depends on 8)

The electronic device of claim 8, wherein the organic electric element comprises at least one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination.