# US 10,873,038 B2 · Organic electroluminescent materials and devices

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- Number: US 10,873,038 B2
- Document ID: US10873038B2
- Status: Granted
- Kind: B2
- Application number: 15/949,601
- Filed: 2018-04-10
- Published: 2019-04-11
- Granted: 2020-12-22
- Earliest claimed: 2011-03-08
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Yonggang Wu; Chuanjun Xia; James Fiordeliso; Suman Layek; Bert Alleyne; Alexey Borisovich Dyatkin; Nasrin Ansari; Scott Beers; Edward Barron; Jason Brooks
- Web page: https://patentgrep.com/patent/US10873038B2

## 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
- H10K 50/11: characterised by the electroluminescent [EL] layers
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- Y10S 428/917: Electroluminescent
- 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
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters.

## Claims

### Claim 1

A compound comprising a ligand L having the formula:
wherein A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R2 and RA may represent mono, di, tri or tetra substitutions;
wherein each of R1, R2 and RA 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 two adjacent substituents of R2 and RA are optionally joined to form a fused ring;
wherein each of X1, X2, X3 and X4 are independently selected from the group consisting of C and N;
wherein at least two of X1, X2, X3 and X4 are N;
wherein the ligand L is coordinated to a metal M having an atomic number greater than 40;
wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand; and
wherein the compound is heteroleptic; and
wherein at least one of the following is true:
(i) R1 is selected from the group consisting of halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, combinations thereof, and partially or fully deuterated variations thereof, and
(ii) RA is an electron donating group with a Hammett sigma constant less than 0.

### Claim 2 (depends on 1)

The compound of claim 1, wherein A is benzene.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1 is alkyl or cycloalkyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R1 is aryl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein RA is an electron donating group with a Hammett sigma constant less than 0.

### Claim 7 (depends on 6)

The compound of claim 6, wherein RA is selected from the group consisting of alkyl, arylamino, alkylamino, aryloxyl, and alkyloxyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the ligand L is selected from the group consisting of:
wherein R3 may represent mono, di, tri or tetra substitutions;
wherein R3 is 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; and
wherein two adjacent substituents of R3 are optionally joined to form a fused ring.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound has a formula selected from the group consisting of:
wherein L′ is a different ligand; and
wherein m is 1, or 2.

### Claim 10 (depends on 9)

The compound of claim 9, wherein L′ is a monoanionic bidentate ligand.

### Claim 11 (depends on 9)

The compound of claim 9, wherein L′ is selected from the group consisting of:
wherein Ra, Rb, and Rc may represent mono, di, tri or tetra substitutions;
wherein Ra, Rb, and Rc 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; and
wherein two adjacent substituents of Ra, Rb, and Rc are optionally joined to form a fused ring.

### Claim 12

A compound selected from the group consisting of:

### Claim 13

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, wherein the organic layer further comprises a compound comprising a ligand L having the formula:
wherein A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R2 and RA may represent mono, di, tri or tetra substitutions;
wherein each of R1, R2 and RA 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 two adjacent substituents of R2 and RA are optionally joined to form a fused ring;
wherein each of X1, X2, X3 and X4 are independently selected from the group consisting of C and N;
wherein at least two of X1, X2, X3 and X4 are N;
wherein the ligand L is coordinated to a metal M having an atomic number greater than 40;
wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand; and
wherein the compound is heteroleptic; and
wherein at least one of the following is true:
(i) R1 is selected from the group consisting of halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, combinations thereof, and partially or fully deuterated variations thereof, and
(ii) RA is an electron donating group with a Hammett sigma constant less than 0.

### Claim 14 (depends on 13)

The first device of claim 13, wherein the organic layer is an emissive layer and the compound comprising the ligand L is an emissive dopant.

### Claim 15 (depends on 14)

The first device of claim 14, wherein the organic layer further comprises a host, comprising at least one of the chemical groups selected from the group consisting of:
wherein each of R′″1 and R′″2 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;
wherein k is an integer from 0 to 20; and
wherein each of X1, X2, X3, X4, X5, X6, X7 and X8 are independently selected from the group consisting of CH and N.

### Claim 16 (depends on 13)

The first device of claim 13, wherein the first device is selected from the group consisting of an organic light emitting device and a consumer product.

### Claim 17

A first device comprising an organic light emitting device, comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound selected from the group consisting of: