# US 9,437,828 B2 · Electroluminescent device using azomethine-lithium-complex as electron injection layer

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- Number: US 9,437,828 B2
- Document ID: US9437828B2
- Status: Granted
- Kind: B2
- Application number: 14/510,526
- Filed: 2014-10-09
- Published: 2015-03-05
- Granted: 2016-09-06
- Earliest claimed: 2006-12-29
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Poopathy Kathirgamanathan; Yun Fu Chan
- Web page: https://patentgrep.com/patent/US9437828B2

## CPC

- H10K 85/30: Coordination compounds
- C07C 251/24: having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
- C07C 255/61: containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- 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 2211/1037: with sulfur
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- C09K 2211/181: of the alkali metals and alkaline earth metals
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/171: {Electron injection layers}
- H10K 85/60: Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence)
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- Y10S 428/917: Electroluminescent
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

In OLEDs, improved efficiency is obtained by compounds which can form inter alia electron injection layers of the formula (I) wherein R1 is a 1-5 ring aryl (including polycyclic), aralkyl or heteroaryl group which is optionally substituted with one or more C1-C4 alkyl, alkoxy or cyano; R2 and R3 together form a 1-5 ring aryl (including polycyclic), aralkyl or heteroaryl group which is optionally substituted with C1-C4 alkyl, alkoxy or cyano; R4 is hydrogen, C1-C4 alkyl or aryl; and Ar is monocyclic, bicyclic or tricyclic aryl or heteroaryl which is optionally substituted with one or more C1-C4-alkyl or alkoxy groups, or an oligomer thereof.

## Claims

### Claim 1

A compound of the formula
wherein
R1 is a 1-5 ring aryl, aralkyl or heteroaryl group which is optionally substituted with one or more C1-C4 alkyl, alkoxy or cyano;
R2 and R3 together form a 1-5 ring aryl, aralkyl or heteroaryl group which is optionally substituted with C1-C4 alkyl, alkoxy or cyano;
R4 is hydrogen, C1-C4 alkyl or aryl; and
Ar is monocyclic, bicyclic or tricyclic aryl or heteroaryl which is optionally substituted with one or more C1-C4-alkyl or alkoxy groups.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 is phenyl or substituted phenyl and R2 and R3 together form phenyl or substituted phenyl.

### Claim 3 (depends on 1)

The compound of claim 1, which is of formula
wherein R1 is phenyl or phenyl substituted with one or more C1-C4 alkyl groups and R2 and R3 together form phenyl or phenyl substituted by one or more C1-C4 alkyl groups, and R4 is hydrogen, C1-C4 alkyl or aryl.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R1 and/or R2 and R3 represent phenyl substituted with one or more methyl groups.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound is selected from the following:

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound is