# US 10,770,663 B2 · Germanium-centered dendrimer compound, and organic optoelectric element comprising same

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- Number: US 10,770,663 B2
- Document ID: US10770663B2
- Status: Granted
- Kind: B2
- Application number: 14/904,109
- Filed: 2014-07-09
- Published: 2016-05-19
- Granted: 2020-09-08
- Earliest claimed: 2013-07-09
- Assignees: Chung Ang University Industry Academic Cooperation Foundation
- Applicants: Chung-Ang University Industry—Academic Cooperation Foundation
- Inventors: Kwang Yong Park; Ho Jun Shon; Tae Won Lee
- Web page: https://patentgrep.com/patent/US10770663B2

## CPC

- C07F 7/30: Germanium compounds
- C09K 11/06: containing organic luminescent materials
- H10K 85/30: Coordination compounds
- 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 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07F 7/02: Silicon compounds
- C07F 7/22: Tin compounds
- C07F 7/24: Lead compounds
- 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
- C09K 2211/188: of other metals not provided for in one of the previous groups
- H10K 30/20: comprising organic-organic junctions, e.g. donor-acceptor junctions
- H10K 30/50: Photovoltaic [PV] devices
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10W 72/923: {Bond pads having multiple stacked layers}
- H10W 72/952: {comprising metals or metalloids, e.g. PbSn, Ag or Cu}
- Y02E 10/549: Organic PV cells
- 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
- H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Germanium-centered dendrimer compounds and organic optoelectronic devices comprising the same are provided. The organic optoelectronic device comprising the compound is capable of implementing high light-emitting ability and light-emitting efficiency, and improving thermal stability (heat resistance) of the organic optoelectronic devices, thereby increasing the lifetime thereof.

## Claims

### Claim 1

A germanium-centered dendrimer compound having the following structure of Formula 1:
wherein:
R1, R2, R3 and R4 are each independently attached at the respective para position and represented by Formula 5:
R5 is hydrogen,
R6 is an aryl group having to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
R7 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms, and
one or more hydrogens in R1 to R4 and R6 to R7 are each independently a compound substituted or not substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heterocyclic group having 3 to 30 carbon atoms, an acyl group having 1 to 30 carbon atoms, an acyloxy group having 6 to 30 carbon atoms, a dialkylamino group having 2 to 30 carbon atoms, a diarylamino group having 12 to 30 carbon atoms, an alkylarylamino group having 7 to 30 carbon atoms, a dialkylphosphino group having 2 to 30 carbon atoms, a diarylphosphino group having 12 to 30 carbon atoms, an alkylarylphosphino group having 7 to 30 carbon atoms, an amine group, a halogen group, a cyano group, a nitro group, a hydroxyl group and a carboxyl group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
the compound of Formula 1 is a germanium-centered symmetrical structure.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound of Formula 1 is one or more selected from the group consisting of Formulae 12 and 14 to 18:

### Claim 4 (depends on 1)

An optoelectronic device comprising the compound of claim 1.

### Claim 5 (depends on 4)

The device of claim 4, wherein the optoelectronic device is an organic light-emitting device, an organic solar cell or an organic semiconductor.

### Claim 6 (depends on 4)

The device of claim 4, wherein the optoelectronic device is an organic light-emitting device, which comprises a first electrode, an organic layer and a second electrode, wherein the organic layer includes one or more of a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and one or more of the layers constituting the organic layer includes said compound.