# US 11,910,708 B2 · Organic electroluminescent materials and devices

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- Number: US 11,910,708 B2
- Document ID: US11910708B2
- Status: Granted
- Kind: B2
- Application number: 17/713,357
- Filed: 2022-04-05
- Published: 2022-07-28
- Granted: 2024-02-20
- Earliest claimed: 2018-02-09
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Jui-Yi Tsai; Alexey Borisovich Dyatkin; Zhiqiang Ji
- Web page: https://patentgrep.com/patent/US11910708B2

## CPC

- H10K 85/342: {comprising iridium}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/17: Carrier injection layers
- H10K 50/18: Carrier blocking layers
- H10K 50/82: Cathodes
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K 2102/321: {Inverted OLED, i.e. having cathode between substrate and anode}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A compound including a first ligand LA selected from the following group: is disclosed.

## Claims

### Claim 1

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 of M(LA)2(LC);
wherein ligand LA is selected from the group consisting of:
wherein A is a 5- or 6-membered aromatic ring;
wherein Y1-Y9 are each independently selected from the group consisting of C and N;
wherein Z is C or N;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein RA, RB, RC, and RD represent mono to a maximum possible number of substitutions, or no substitution;
wherein each RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RD is fluorine;
wherein any two RA substituents can be joined or fused together to form a ring;
wherein the organic layer is an emissive layer and the compound is an emissive dopant;
wherein the organic layer further comprises a host;
wherein the host comprises at least one chemical group selected from the group consisting of naphthalene, triazine, carbazole, dibenzofuran, and dibenzothiophene; and
wherein LC has the structure
wherein Ra, Rb, and Rc are each independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

### Claim 2 (depends on 1)

The OLED of claim 1, wherein RA, RB, RC, and RD are each a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

### Claim 3 (depends on 1)

The OLED of claim 1, wherein Y1 to Y9 are each C.

### Claim 4 (depends on 1)

The OLED of claim 1, wherein at least one of Y1 to Y9 is N; or one of Y1 to Y3 is N.

### Claim 5 (depends on 1)

The OLED of claim 1, wherein Z is N, Y1 is C.

### Claim 6 (depends on 1)

The OLED of claim 1, wherein A is selected from the group consisting of pyridine, pyrimidine, imidazole, pyrazole, and N-heterocyclic carbene.

### Claim 7 (depends on 1)

The OLED of claim 1, wherein LA is selected from the group consisting of:
wherein RE is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combination thereof.

### Claim 8

An emissive layer comprising:
a host comprising at least one chemical group selected from the group consisting of naphthalene, triazine, carbazole, dibenzofuran, and dibenzothiophene; and
an emissive dopant;
wherein the emissive dopant is a compound having a formula of M(LA)2(LC);
wherein ligand LA is selected from the group consisting of:
wherein A is a 5- or 6-membered aromatic ring;
wherein Y1-Y9 are each independently selected from the group consisting of C and N;
wherein Z is C or N;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein RA, RB, RC, and RD represent mono to a maximum possible number of substitutions, or no substitution;
wherein each RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RD is fluorine;
wherein any two RA substituents can be joined or fused together to form a ring;
wherein the organic layer is an emissive layer and the compound is an emissive dopant;
wherein the organic layer further comprises a host;
wherein the host comprises at least one chemical group selected from the group consisting of naphthalene, triazine, carbazole, dibenzofuran, and dibenzothiophene; and
wherein LC has the structure
wherein Ra, Rb, and Rc are each independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

### Claim 9 (depends on 8)

The emissive layer of claim 8, wherein the host is selected from the group consisting of:
and combinations thereof.

### Claim 10

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 formula of M(LA)2(LC);
wherein ligand LA is selected from the group consisting of:
wherein A is a 5- or 6-membered aromatic ring;
wherein Y1-Y9 are each independently selected from the group consisting of C and N;
wherein Z is C or N;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein RA, RB, RC, and RD represent mono to a maximum possible number of substitutions, or no substitution;
wherein each RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RD is fluorine;
wherein any two RA substituents can be joined or fused together to form a ring;
wherein the organic layer is an emissive layer and the compound is an emissive dopant;
wherein the organic layer further comprises a host;
wherein the host comprises at least one chemical group selected from the group consisting of naphthalene, triazine, carbazole, dibenzofuran, and dibenzothiophene; and
wherein LC has the structure
wherein Ra, Rb, and Rc are each independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

### Claim 11 (depends on 10)

The consumer product of claim 10, wherein the consumer product is one 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 mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display (displays that are 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, a light therapy device, and a sign.