# US 10,770,664 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 10,770,664 B2
- Document ID: US10770664B2
- Status: Granted
- Kind: B2
- Application number: 15/248,317
- Filed: 2016-08-26
- Published: 2017-03-23
- Granted: 2020-09-08
- Earliest claimed: 2015-09-21
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Jui-Yi Tsai; Chuanjun Xia; Pierre-Luc T Boudreault; Ana M. Lopez; Ainhoa San Torcuato; Enrique Oñate; Miguel A. Esteruelas
- Web page: https://patentgrep.com/patent/US10770664B2

## CPC

- H10K 85/342: {comprising iridium}
- C07F 15/0033: {Iridium compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- 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 2101/10: Triplet emission
- 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

## Abstract

This invention discloses iridium complexes containing one tetradentate ligand and one bidentate ligand. The heteroleptic iridium complexes showed desired properties such as good EQE, LT, and CIE.

## Claims

### Claim 1

A compound having a formula Ir(LA)(LB)(LC);
wherein the ligand LA, LB, and LC are each a mono-anionic bidentate ligand coordinated to Ir forming a 5-member cyclometalated ring;
wherein LA and LB are covalently linked by a linking group and are each independently selected from the group consisting of:
wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′ and R″ are each 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 Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein one of Ra, Rb, Rc, and Rd in ligand LA is joined with one of Ra, Rb, Rc, and Rd in ligand LB;
wherein LC is not linked to LA and LB, and is selected from the group consisting of:
wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution; and
wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein LC is selected from the group consisting of:
wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution; and
wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

### Claim 3 (depends on 1)

The compound of claim 1, wherein LC is selected from the group consisting of:
wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution; and
wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
wherein LC is selected from the group consisting of:
wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
wherein each R1 to R7, Ra, Rb, and Rc may represent from mono substitution to the possible maximum number of substitution, or no substitution; and
wherein R1 to R7, Ra, Rb, and Rc are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

### Claim 6 (depends on 1)

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

### Claim 7

An organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula Ir(LA)(LB)(LC);
wherein the ligand LA, LB, and LC are each a mono-anionic bidentate ligand coordinated to Ir forming a 5-member cyclometalated ring;
wherein LA and LB are covalently linked by a linking group and are each independently selected from the group consisting of:
wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′ and R″ are each 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 Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein one of Ra, Rb, Rc, and Rd in ligand LA is joined with one of Ra, Rb, Rc, and Rd in ligand LB;
wherein LC is not linked to LA and LB, and is selected from the group consisting of:
wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution; and
wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

### Claim 8 (depends on 7)

The OLED of claim 7, wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.

### Claim 9 (depends on 7)

The OLED of claim 7, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

### Claim 10 (depends on 7)

The OLED of claim 7, wherein the organic layer further comprises a host,
wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡CCnH2n+1, Ar1, Ar1—Ar2, CnH2n—Ar1, or no substitution;
wherein n is from 1 to 10; and
wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

### Claim 11 (depends on 7)

The OLED of claim 7, wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

### Claim 12 (depends on 7)

The OLED of claim 7, wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
and combinations thereof.

### Claim 13 (depends on 7)

The OLED of claim 7, wherein the organic layer further comprises a host, wherein the host comprises a metal complex.

### Claim 14

A formulation comprising a compound having a formula Ir(LA)(LB)(LC);
wherein the ligand LA, LB, and LC are each a mono-anionic bidentate ligand coordinated to Ir forming a 5-member cyclometalated ring;
wherein LA and LB are covalently linked by a linking group and are each independently selected from the group consisting of:
wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′ and R″ are each 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 Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein one of Ra, Rb, Rc, and Rd in ligand LA is joined with one of Ra, Rb, Rc, and Rd in ligand LB;
wherein LC is not linked to LA and LB, and is selected from the group consisting of:
wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution; and
wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.