# US 11,910,700 B2 · Heteroleptic iridium complexes as dopants

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- Number: US 11,910,700 B2
- Document ID: US11910700B2
- Status: Granted
- Kind: B2
- Application number: 17/746,351
- Filed: 2022-05-17
- Published: 2022-09-22
- Granted: 2024-02-20
- Earliest claimed: 2009-03-23
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Gregg Kottas; Nasrin Ansari; Zeinab Elshenawy; Alan DeAngelis; Chuanjun Xia
- Web page: https://patentgrep.com/patent/US11910700B2

## CPC

- 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}
- C07F 15/0033: {Iridium compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- 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 50/12: comprising dopants
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- 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

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

## Claims

### Claim 1

A compound having the formula:
wherein R1 and R2 are optionally linked;
wherein the sum of the number of carbon atoms in R1 and R2 is at least 2;
wherein any two R3, R4, R5, or R6 are optionally linked;
wherein Ra and Rb represent mono-, di-, tri- or tetra-substitution;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein Ra, Rb, R, R′, R1, R2, R3, R4, R5, and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
at least one of R1 or R2 comprises a silyl group comprising and at least one moiety selected from the group consisting of cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and
wherein n is 1 or 2.

### Claim 2 (depends on 1)

The compound of claim 1, wherein n is 2.

### Claim 3 (depends on 1)

The compound of claim 1, wherein X is O.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1 is hydrogen and R2 comprises a silyl group comprising at least one moiety selected from the group consisting of cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R1 comprises a silyl group comprising at least one moiety selected from the group consisting of cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and R2 is hydrogen.

### Claim 6 (depends on 1)

The compound of claim 1, wherein each of R1 and R2 independently comprises a silyl group comprising at least one moiety selected from the group consisting of cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R1 or R2 are independently selected from the group consisting of branched alkyl, cyclic alkyl, bicyclic alkyl, and multicyclic alkyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R1 or R2 is iso-propyl.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R1 or R2 contain one or more deuterium atoms.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R1 and R2 contain one or more deuterium atoms.

### Claim 11 (depends on 1)

The compound of claim 1, wherein R3, R4, R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, alkyl, aryl, and combinations thereof.

### Claim 12 (depends on 1)

The compound of claim 1, wherein at least one of R1 and R2 comprises a silyl group comprising at least one aryl or heteroaryl.

### Claim 13 (depends on 1)

The compound of claim 1, wherein R3, R4, R5 or R6 contain one or more deuterium atoms.

### Claim 14

A first device comprising a first organic light emitting device, further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:
wherein R1 and R2 are optionally linked;
wherein the sum of the number of carbon atoms in R1 and R2 is at least 2;
wherein any two R3, R4, R5, or R6 are optionally linked;
wherein Ra and Rb represent mono-, di-, tri- or tetra-substitution;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein Ra, Rb, R, R′, R1, R2, R3, R4, R5, and R6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
at least one of R1 or R2 comprises a silyl group comprising at least one moiety selected from the group consisting of cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and
wherein n is 1 or 2.

### Claim 15 (depends on 14)

The first device of claim 14, wherein the first device is a consumer product.

### Claim 16 (depends on 14)

The first device of claim 14, wherein the first device is an organic light-emitting device.

### Claim 17 (depends on 14)

The first device of claim 14, wherein the first device comprises a lighting panel.

### Claim 18 (depends on 14)

The first device of claim 14, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

### Claim 19 (depends on 14)

The first device of claim 14, wherein the organic layer further comprises a host having the formula:

### Claim 20 (depends on 14)

The first device of claim 14, wherein the organic layer further comprises a host selected from the group consisting of:
and combinations thereof.