# US 10,873,037 B2 · Organic electroluminescent materials and devices

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- Number: US 10,873,037 B2
- Document ID: US10873037B2
- Status: Granted
- Kind: B2
- Application number: 15/925,959
- Filed: 2018-03-20
- Published: 2018-10-04
- Granted: 2020-12-22
- Earliest claimed: 2017-03-28
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Scott Joseph; Pierre-Luc T. Boudreault
- Web page: https://patentgrep.com/patent/US10873037B2

## CPC

- C07F 15/0033: {Iridium compounds}
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- C09K 2211/1029: containing one nitrogen atom as the 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 50/155: comprising dopants
- H10K 50/165: comprising dopants
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- H10K 50/18: Carrier blocking layers
- H10K 50/181: {Electron blocking layers}
- H10K 2101/10: Triplet emission
- 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

## Abstract

This invention relates to novel ligands for metal complexes used in OLED devices. These ligands comprise an aryl ketone or aldehyde and lead to improved device properties including increased efficiency of dopants, increased lifetimes, and the ability to tune emission colors.

## Claims

### Claim 1

A heteroleptic compound having a formula M(LA)n(LB)3−n:
wherein the ligand LA is
wherein the ligand LB is
wherein n is 1 or 2;
wherein rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein RA, RB, and RC each independently represents mono to the maximum possible number of substitution, or no substitution;
wherein X1 represents a carbon, X2 represents a nitrogen, and X3 and X4 each independently represents a carbon or nitrogen;
wherein each R, RA, RB, and RC is 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;
wherein any adjacent substituents are optionally joined or fused to form a ring;
wherein at least one of RB is not hydrogen or deuterium;
wherein the ligand LA is coordinated to a metal M;
wherein the metal M can be coordinated to other ligands; and
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

### Claim 2 (depends on 1)

The compound of claim 1, wherein each R, RA, RB, and RC is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

### Claim 3 (depends on 1)

The compound of claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

The compound of claim 1, wherein rings A and C are benzene.

### Claim 6 (depends on 1)

The compound of claim 1, wherein ring B is selected from the group consisting of pyridine, pyrimidine, triazine, imidazole, pyrazole, oxazole, thiazole, and imidazole derived carbene.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 8)

The compound of claim 8, wherein the compound is the Compound x having the formula Ir(LAi)2(LBj);
wherein x=74i+j−74; i is an integer from 1 to 126, and j is an integer from 1 to 74;
wherein LBj has the following formula:

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

A formulation comprising a compound according to claim 1.

### Claim 12 (depends on 1)

The compound of claim 1, wherein M is Ir.

### Claim 13

An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a heteroleptic compound having a formula M(LA)n(LB)3−n:
wherein the ligand LA is
wherein the ligand LB is
wherein n is 1 or 2;
wherein rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein RA, RB, and RC each independently represents mono to the maximum possible number of substitution, or no substitution;
wherein X1 represents a carbon, X2 represents a nitrogen, and X3 and X4 each independently represents a carbon or nitrogen;
wherein X1 is an anionic donor atom, and X2 is a neutral donor atom;
wherein each R, RA, RB, and RC is 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;
wherein any adjacent substituents are optionally joined or fused to form a ring;
wherein at least one of RB is not hydrogen or deuterium;
wherein the ligand LA is coordinated to a metal M;
wherein the metal M can be coordinated to other ligands; and
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

### Claim 14 (depends on 13)

The OLED of claim 13, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

### Claim 15 (depends on 13)

The OLED of claim 13, wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

### Claim 16 (depends on 13)

The OLED of claim 13, wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
and combinations thereof.

### Claim 17 (depends on 13)

The OLED of claim 13, wherein the organic layer further comprises a host, wherein the host comprises a metal complex.

### Claim 18

A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a heteroleptic compound having a formula M(LA)n(LB)3−n:
wherein the ligand LA is
wherein the ligand LB is
wherein n is 1 or 2;
wherein rings A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;
wherein each RA, RB, and RC independently represents mono to the maximum possible number of substitution, or no substitution;
wherein X1 represents a carbon, X2 represents a nitrogen, and X3 and X4 each independently represents a carbon or nitrogen;
wherein each R, RA, RB, and RC is 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;
wherein any adjacent substituents are optionally joined or fused to form a ring;
wherein at least one of RB is not hydrogen or deuterium;
wherein the ligand LA is coordinated to a metal M;
wherein the metal M can be coordinated to other ligands; and
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

### Claim 19 (depends on 18)

The consumer product of claim 18, wherein the consumer product is selected from the group consisting of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video walls comprising multiple displays tiled together, a theater or stadium screen, and a sign.