# US 11,910,701 B2 · Organic electroluminescent materials and devices

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

- Number: US 11,910,701 B2
- Document ID: US11910701B2
- Status: Granted
- Kind: B2
- Application number: 18/180,664
- Filed: 2023-03-08
- Published: 2023-09-28
- Granted: 2024-02-20
- Earliest claimed: 2009-03-23
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Chuanjun Xia; Raymond C. Kwong; Suman Layek
- Web page: https://patentgrep.com/patent/US11910701B2

## CPC

- H10K 85/342: {comprising iridium}
- C07F 15/0033: {Iridium compounds}
- C09K 11/06: containing organic luminescent materials
- H05B 33/10: Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur 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 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Novel compounds comprising heteroleptic iridium complexes are provided. The compounds have a particular combination of ligands which includes a single pyridyl dibenzo-substituted ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants, to provide devices having improved efficiency, lifetime, and manufacturing.

## Claims

### Claim 1

A compound comprising a heteroleptic iridium complex having the formula:
wherein X is selected from the group consisting of NR, O, S, BR, and Se;
wherein R is selected from hydrogen and alkyl;
wherein R1, R2, R3, and R4 may represent mono, di, tri, or tetra substitutions;
wherein each of R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and aryl; and
wherein at least one R1, R2, R3, or R4 is aryl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 and R4 are independently selected from the group consisting of hydrogen and alkyl having four or fewer carbon atoms.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 and R4 are independently selected from the group consisting of hydrogen and methyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R2 and R3 are independently selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms and aryl with 6 or fewer atoms in the ring.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R2 and R3 are independently selected from the group consisting of hydrogen, methyl and phenyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein each R1, R2, R3, and R4 is independently selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms and aryl with 6 or fewer atoms in the ring; and
wherein at least one R1, R2, R3, or R4 is aryl with 6 or fewer atoms in the ring.

### Claim 7 (depends on 1)

The compound of claim 1, wherein each R1, R2, R3, and R4 is independently selected from the group consisting of hydrogen, methyl and phenyl; and
wherein at least one R1, R2, R3, or R4 is phenyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein X is NR and R has 4 or fewer carbon atoms.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound has the formula:

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound has the formula:

### Claim 11 (depends on 1)

The compound of claim 1, wherein the compound has the formula:

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

The compound of claim 1, wherein X is O.

### Claim 14 (depends on 1)

The compound of claim 1, wherein X is S.

### Claim 15 (depends on 1)

The compound of claim 1, wherein X is NR.

### Claim 16

A first device comprising an organic light emitting device, further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, the organic layer further comprising a compound comprising a heteroleptic iridium complex having the formula:
wherein X is selected from the group consisting of NR, O, S, BR, and Se;
wherein R is selected from hydrogen and alkyl;
wherein R1, R2, R3 and R4 may represent mono, di, tri, or tetra substitutions;
wherein each of R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, alkyl, and aryl; and
wherein at least one R1, R2, R3, or R4 is aryl.

### Claim 17 (depends on 16)

The device of claim 16, wherein the first device is a consumer product.

### Claim 18 (depends on 16)

The device of claim 16, wherein the compound is selected from the group consisting of:

### Claim 19 (depends on 16)

The device of claim 16, wherein the organic layer further comprises a host.

### Claim 20 (depends on 19)

The device of claim 19, wherein the host has the formula:
wherein R′1, R′2, R′3, R′4, R′5, and R′6 may represent mono, di, tri, or tetra substitutions; and
wherein each of R′1, R′2, R′3, R′4, R′5, and R′6 are independently selected from the group consisting of hydrogen, alkyl, and aryl.