# US 12,193,319 B2 · Organic electroluminescent materials and devices

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- Number: US 12,193,319 B2
- Document ID: US12193319B2
- Status: Granted
- Kind: B2
- Application number: 18/353,347
- Filed: 2023-07-17
- Published: 2023-11-09
- Granted: 2025-01-07
- Earliest claimed: 2018-11-28
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Tyler Fleetham; Nicholas J. Thompson
- Web page: https://patentgrep.com/patent/US12193319B2

## CPC

- H10K 85/346: {comprising platinum}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- 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 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- 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 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

Provided are organometallic compounds. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize both a disclosed compound and a Pt complex compound.

## Claims

### Claim 1

A compound having the formula:
wherein X5-X20 are each independently C or N;
each of R6, R7, R8, R9 and R10 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein R10 is a substituted biphenyl;
wherein the substituted biphenyl is substituted with at least one carbazole.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the substituted biphenyl R10 is substituted with at least two carbazole moieties.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the substituted biphenyl R10 is substituted with an unsubstituted carbazole.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the substituted biphenyl R10 is a dicarbazole biphenyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein each phenyl of the substituted biphenyl R10 is substituted with at least one carbazole.

### Claim 6 (depends on 1)

The compound of claim 1, wherein at least one phenyl of the substituted biphenyl R10 is substituted with at least two carbazole moieties.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the substituted biphenyl R10 is [1,1′-biphenyl]-4-yl that is substituted with at least one carbazole.

### Claim 8 (depends on 1)

The compound of claim 1, wherein at least one carbazole is substituted ortho to the biphenyl bond.

### Claim 9 (depends on 1)

The compound of claim 1, wherein at least two carbazoles are substituted ortho to the biphenyl bond.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound comprises a 3,9 biscarbazole.

### Claim 11 (depends on 1)

The compound of claim 1, wherein the compound comprises at least four carbazole moieties.

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is partially or fully deuterated.

### Claim 13 (depends on 1)

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

### Claim 14

An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an emissive layer disposed between the anode and the cathode, the emissive layer comprising a host compound,
wherein the host compound has the formula of
wherein X5-X20 are each independently C or N;
each of R6, R7, R8, R9 and R10 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein R10 is a substituted biphenyl;
wherein the substituted biphenyl is substituted with at least one carbazole.

### Claim 15 (depends on 14)

The OLED of claim 14, wherein the host compound is selected from the group consisting of

### Claim 16 (depends on 14)

The OLED of claim 14, wherein the emissive layer comprises an additional compound, and the additional compound is also a co-host which comprises a chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, pyridine, pyrimidine, triazine, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

### Claim 17

A consumer product comprising an organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an emissive layer disposed between the anode and the cathode, the emissive layer comprising a host compound, wherein the host compound has the formula of
wherein X5-X20 are each independently C or N;
each of R6, R7, R8, R9 and R10 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein R10 is a substituted biphenyl;
wherein the substituted biphenyl is substituted with at least one carbazole.

### Claim 18 (depends on 17)

The consumer product of claim 17, wherein the host compound is selected from the group consisting of

### Claim 19 (depends on 17)

The consumer product of claim 17, wherein the consumer product is selected from the group consisting of a flat panel 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 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, a 3-D display, a virtual reality or augmented reality display, a vehicle, a large area wall, a theater or stadium screen, and a sign.

### Claim 20 (depends on 17)

The consumer product of claim 17, wherein the emissive layer of the OLED comprises an additional compound, and the additional compound is also a co-host which comprises a chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, pyridine, pyrimidine, triazine, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).