# US 11,114,626 B2 · Metal compounds, methods, and uses thereof

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- Number: US 11,114,626 B2
- Document ID: US11114626B2
- Status: Granted
- Kind: B2
- Application number: 16/834,229
- Filed: 2020-03-30
- Published: 2020-07-16
- Granted: 2021-09-07
- Earliest claimed: 2012-09-24
- Assignees: Arizona Board of Regents on behalf of Arizona State University
- Applicants: Arizona Board of Regents On Behalf of Arizona State University
- Inventors: Jian Li; Guijie Li
- Web page: https://patentgrep.com/patent/US11114626B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 15/0086: {Platinum compounds}
- H10K 85/346: {comprising platinum}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1037: with sulfur
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/125: specially adapted for multicolour light emission, e.g. for emitting white light
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Disclosed herein are metal compounds useful in devices, such as, for example, OLEDs.

## Claims

### Claim 1

A compound having the formula
wherein each of L1, L2, L3, and L4 independently is a substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, carbene, or N-heterocyclic carbene;
wherein each of Z1, Z2, and Z3 independently is present or absent, and if present each of Z1, Z2, and Z3 independently is A, A1, or A2;
wherein each of A, A1, or A2 independently is O, S, S═O, SO2, Se, NR3, PR3, RP═O, CR1R2, C═O, SiR1R2, GeR1R2, BH, P(O)H, PH, NH, CR1H, CH2, SiH2, SiHR1, BH, or BR3;
wherein M is Pt, Pd, Au, Ir, Rh, Ru, Fe, Co, Ni, Cu, Zn, Ag, Hg, Cd, or Zr;
wherein at least one of L1, L2, L3, or L4 comprises
wherein m and n independently is an integer from 0 to 4;
wherein each of V, X, and Y independently is V1, V2, V3, V4, O, S, S═O, SO2, Se, N, NR3, PR3, R1P═O, CR1R2, C═O, SiR1R2, GeR1R2, BH, P(O)H, PH, NH, CR1H, CH2, SiH2, SiHR1, BH, or BR3, or any one of
wherein at least one of V, X, or Y is V1, V2, V3, or V4;
wherein m and n independently is an integer from 0 to 4;
wherein each of V1, V2, V3, and V4 independently is coordinated to M;
wherein each of V1, V2, V3, and V4 independently is N, C, CH, P, B, SiH, or Si; and
wherein each of R, R1, R2, R3, and R4, independently is hydrogen, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, deuterium, halogen, hydroxyl , thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, substituted silyl, or polymerizable, or any conjugate or combination thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein one of Z1, Z2, or Z3 is present and two of Z1, Z2, and Z3 is not present.

### Claim 3 (depends on 1)

The compound of claim 1, wherein two of Z1, Z2, and Z3 is present and one of Z1, Z2, or Z3 is not present.

### Claim 4 (depends on 1)

The compound of claim 1, wherein each of Z1, Z2, and Z3 independently is absent.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound has the structure

### Claim 6 (depends on 1)

The compound of claim 1, wherein at least one of L1, L2, L3, or L4, together with V1, V2, V3, and V4, respectively, comprises one or more of the following structures:

### Claim 7 (depends on 1)

The compound of claim 1, wherein
has the structure

### Claim 8 (depends on 1)

The compound of claim 1, wherein
has the structure

### Claim 9 (depends on 1)

The compound of claim 1, wherein at least one of V1, V2, V3, or V4 is N.

### Claim 10 (depends on 1)

The compound of claim 1, wherein at least one of V1, V2, V3, or V4 is C.

### Claim 11 (depends on 1)

The compound of claim 1, wherein M is Pt or Pd.

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is represented by one of the following structures:

### Claim 13 (depends on 12)

An organic light emitting device comprising one or more compounds of claim 12.

### Claim 14 (depends on 13)

A full color display comprising one or more light emitting devices of claim 13.

### Claim 15 (depends on 1)

An organic light emitting device comprising one or more compounds of claim 1.

### Claim 16 (depends on 15)

A full color display comprising one or more light emitting devices of claim 15.