# US 11,114,624 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 11,114,624 B2
- Document ID: US11114624B2
- Status: Granted
- Kind: B2
- Application number: 16/821,297
- Filed: 2020-03-17
- Published: 2020-09-24
- Granted: 2021-09-07
- Earliest claimed: 2016-06-20
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Mingjuan Su; Walter Yeager; Alan Deangelis; Bin Ma; Jui-Yi Tsai; Lichang Zeng; Chuanjun Xia
- Web page: https://patentgrep.com/patent/US11114624B2

## CPC

- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- C07F 15/0033: {Iridium compounds}
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/655: {comprising only sulfur as heteroatom}
- C07D 209/82: Carbazoles; Hydrogenated carbazoles
- C07D 239/70: condensed with carbocyclic rings or ring systems
- C07D 333/76: Dibenzothiophenes
- 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 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention includes a new series of benzofused heterocyclic ligands for metal complexes. These complexes show promising photophysical performance when incorporated into OLEDs.

## Claims

### Claim 1

A compound comprising a first ligand LA having Formula I:
wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein RB represents mono to the possible maximum number of substitution, or no substitution;
wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
wherein A1, A2, A3, and A4 are each independently CR or N;
wherein ring C is a 5 or 6-membered aromatic ring;
n is 0 or 1;
wherein when n is 0, A8 is not present, and A5, A6, and A7 are each independently selected from the group consisting of CR, NR′, O, S, and Se;
wherein when n is 1, A5, A6, A7, and A8 are each independently CR or N, and at least two adjacent A1, A2, A3, A4, A5, A6, A7, and A8 are CR and the Rs are joined together to form a six-membered ring fused to ring A or ring C;
wherein, if (i) n=0, (ii) at least two adjacent A5, A6, and A7, are CR and the Rs are joined together to form a six-membered ring fused to ring C, and (iii) ring B is imidazole, then Z1 is carbene carbon;
wherein each R and R′ in CR or NR′ can be the same or different;
wherein X is O, S, or Se;
wherein R, R′ 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, 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 into a ring;
wherein the ligand LA is coordinated to a metal M;
wherein the metal M is bonded to ring A through a M-C bond;
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 M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

### 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 n is 1, and each A1, A2, A3, A4, A5, A6, A7, and A8 is independently a CR.

### Claim 5 (depends on 1)

The compound of claim 1, wherein n is 1, and at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is N.

### Claim 6 (depends on 1)

The compound of claim 1, wherein n is 1, and at least two adjacent A1, A2, A3, A4, A5, A6, A7, and A8 are CR and the Rs are joined together to form a phenyl ring fused to ring A or ring C.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the ligand LA is selected from the group consisting of:
wherein Y is selected from the group consisting of O, S, Se, and NR′; and
wherein RA and RC have the same definition as RB.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound has the formula of M(LA)x(LB)y(LC)z;
wherein LB is a second ligand, and LC is a third ligand, and LB and LC can be the same or different;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein the second ligand LB and the third ligand Lc are each independently selected from the group consisting of:
wherein X1 to X13 are each 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′, R″, 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, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.

### Claim 9 (depends on 8)

The compound of claim 8, wherein the ligand LA is selected from the group consisting of:

### Claim 10 (depends on 9)

The compound of claim 9, wherein the compound is the Compound A-x having the formula Ir(LAi)(LBj)2;
wherein x=300i+j−300; i is an integer from 1 to 860, and j is an integer from 1 to 300; and
wherein the ligand LB is selected from the group consisting of:

### Claim 11 (depends on 8)

The compound of claim 8, wherein the compound has the formula of Ir(LA)n(LB)3-n or Ir(LA)(LB)(LC); wherein n is 1, 2, or 3.

### Claim 12 (depends on 8)

The compound of claim 8, wherein the ligand LB is selected from the group consisting of:

### Claim 13 (depends on 8)

The compound of claim 8, wherein the compound has formula of Ir(LA)2(Lc);
wherein the ligand Lc is selected from the group consisting of:

### Claim 14 (depends on 1)

A formulation comprising a compound of claim 1.

### Claim 15

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 comprising a first ligand LA having Formula I:
wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein RB represents mono to the possible maximum number of substitution, or no substitution;
wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
wherein A1, A2, A3, and A4 are each independently CR or N;
wherein ring C is a 5 or 6-membered aromatic ring;
n is 0 or 1;
wherein when n is 0, A8 is not present, and A5, A6, and A7 are each independently selected from the group consisting of CR, NR′, O, S, and Se;
wherein when n is 1, A5, A6, A7, and A8 are each independently a CR or N, and at least two adjacent A1, A2, A3, A4, A5, A6, A7, and A8 are CR and the Rs are joined together to form a six-membered ring fused to ring A or ring C;
wherein, if (i) n=0, (ii) at least two adjacent A5, A6, and A7, are CR and the Rs are joined together to form a six-membered ring fused to ring C, and (iii) ring B is imidazole, then Z1 is carbene carbon;
wherein each R and R′ in CR or NR′ can be the same or different;
wherein X is O, S, or Se;
wherein R, R′ 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, 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 into a ring;
wherein the ligand LA is coordinated to a metal M;
wherein the metal M is bonded to ring A through a M-C bond;
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 16 (depends on 15)

The OLED of claim 15, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

### Claim 17 (depends on 15)

The OLED of claim 15, 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, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

### Claim 18 (depends on 15)

The OLED of claim 15, wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
and combinations thereof.

### Claim 19

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 compound having a ligand of Formula I:
wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein RB represents mono to the possible maximum number of substitution, or no substitution;
wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
wherein A1, A2, A3, and A4 are each independently CR or N;
wherein ring C is a 5 or 6-membered aromatic ring;
n is 0 or 1;
wherein when n is 0, A8 is not present, and A5, A6, and A7 are each independently selected from the group consisting of CR, NR′, O, S, and Se;
wherein when n is 1, A5, A6, A7, and A8 are each independently CR or N, and at least two adjacent A1, A2, A3, A4, A5, A6, A7, and A8 are CR and the Rs are joined together to form a six-membered ring fused to ring A or ring C;
wherein, if (i) n=0, (ii) at least two adjacent A5, A6, and A7, are CR and the Rs are joined together to form a six-membered ring fused to ring C, and (iii) ring B is imidazole, then Z1 is carbene carbon;
wherein each R and R′ in CR or NR′ can be the same or different;
wherein X is O, S, or Se;
wherein R, R′ 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, 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 into a ring;
wherein the ligand LA is coordinated to a metal M;
wherein the metal M is bonded to ring A through a M-C bond;
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 20 (depends on 19)

The consumer product of claim 19, wherein the consumer product is one of a flat panel display, a computer monitor, a medical monitors 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 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 wall comprising multiple displays tiled together, a theater or stadium screen, and a sign.