# US 11,910,702 B2 · Organic electroluminescent devices

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- Number: US 11,910,702 B2
- Document ID: US11910702B2
- Status: Granted
- Kind: B2
- Application number: 16/158,406
- Filed: 2018-10-12
- Published: 2019-05-09
- Granted: 2024-02-20
- Earliest claimed: 2017-11-07
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Eric A. Margulies; Zhiqiang Ji; Nicholas J. Thompson; Geza Szigethy; Michael S. Weaver; Jerald Feldman
- Web page: https://patentgrep.com/patent/US11910702B2

## CPC

- H10K 85/351: {Metal complexes comprising lanthanides or actinides, e.g. comprising europium}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/125: specially adapted for multicolour light emission, e.g. for emitting white light
- H10K 50/131: {with spacer layers between the electroluminescent layers}
- H10K 50/171: {Electron injection layers}
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- H10K 85/348: {comprising osmium}
- H10K 85/371: {Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver}
- 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: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An OLED structure including a first organic layer disposed between the anode and the cathode is disclosed. The first organic layer includes a primary phosphorescent emitter and a first host, and where one of the following conditions is true: (1) the first organic layer further includes a secondary emitter; or (2) the OLED further includes a second organic layer disposed between the anode and the cathode, wherein the second organic layer includes a secondary emitter. The phosphorescent emitter has a peak emission wavelength λmax that is ≥600 nm and ≤750 nm, the secondary emitter has a peak emission wavelength λmax that is ≥750 nm, and the first host has a lowest excited state triplet energy T1 that is at least 0.1 eV higher than that of the primary phosphorescent emitter.

## Claims

### Claim 1

An organic light emitting device (OLED) comprising:
an anode;
a cathode;
a first organic layer, disposed between the anode and the cathode;
wherein the first organic layer comprises a primary phosphorescent emitter and a first host;
wherein one of the following conditions is true:
(1) the first organic layer further comprises a secondary emitter; or
(2) the OLED device further comprises a second organic layer disposed between the anode and the cathode, wherein the second organic layer comprises a secondary emitter;
wherein the primary phosphorescent emitter has a formula of M1(LA)x(LB)y(LC)z;
wherein LA, LB and LC are each a bidentate ligand;
wherein M1 is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; and
wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M1;
wherein LA is selected from the group consisting of:
LB and LC are each independently selected from the group consisting of:
wherein,
each X1 to X10 are independently selected from the group consisting of C and N;
at least one of X1 to X10 is N;
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″;
R′ and R″ are optionally fused or joined to form a ring;
each Ra, Rb, and Rc represents from mono substitution to the maximum possible number of substitutions, or no substitution;
R′, R″, Ra, Rb, and Rc are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, benzonitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two adjacent substituents of Ra, Rb, and Rc can be fused or joined to form a ring or form a multidentate ligand;
wherein the primary phosphorescent emitter has a peak emission wavelength λmax that is ≥600 nm and ≤750 nm;
wherein the secondary emitter is a near-infrared emitter that has a peak emission wavelength λmax that is between 750 nm and 2500 nm;
wherein the first host has a lowest excited state triplet energy T1 that is at least 0.1 eV higher than that of the primary phosphorescent emitter;
wherein the secondary emitter is selected from the group consisting of: a fluorescent emitter, a thermally activated delayed fluorescence emitter, and an emitter containing an unpaired electron in its ground state,
whereby Dexter energy transfer from the primary emitter to the secondary emitter is minimized to prevent formation of fluorophore triplet excitons.

### Claim 2 (depends on 1)

The OLED of claim 1, wherein the condition (1) is true, and the first organic layer is the only layer containing the secondary emitter.

### Claim 3 (depends on 1)

The OLED of claim 1, wherein the condition (2) is true, and the second organic layer is the only layer containing the secondary emitter.

### Claim 4 (depends on 1)

The OLED of claim 1, wherein the secondary emitter has a peak absorption wavelength and the difference between the peak emission wavelength λmax of the primary phosphorescent emitter and the peak absorption wavelength λmax of the secondary emitter is less than 200 nm.

### Claim 5 (depends on 1)

The OLED of claim 1, wherein the first organic layer and the second organic layer are separated by one or more additional organic layers.

### Claim 6 (depends on 5)

The OLED of claim 5, wherein the separation between the first organic layer and the second organic layer is ≥1 nm.

### Claim 7 (depends on 1)

The OLED of claim 1, wherein the condition (1) is true, and wherein the concentration of the primary phosphorescent emitter and concentration of the secondary emitter in the first organic layer are different.

### Claim 8 (depends on 1)

The OLED of claim 1, wherein the condition (1) is true, and wherein the concentration of the primary phosphorescent emitter and the concentration of the secondary emitter in the first organic layer are each ≤10 wt. %.

### Claim 9 (depends on 1)

The OLED of claim 1, wherein the condition (1) is true, and wherein an average intermolecular distance between the primary phosphorescent emitter and the secondary emitter is ≥8 Å.

### Claim 10 (depends on 1)

The OLED of claim 1, wherein the condition (2) is true, whereby the primary emitter and the secondary emitter are spatially isolated to minimize any Dexter energy transfer and prevent formation of fluorophore triplet excitons.

### Claim 11 (depends on 10)

The OLED of claim 10, wherein the first organic layer and the second organic layer are separated by one or more layers of host or transport materials to achieve an interlayer separation distance of greater than 1 nm.

### Claim 12 (depends on 1)

The OLED of claim 1, wherein the condition (1) is true and the primary and secondary emitters are doped in the first organic layer at doping concentrations that result in donor-acceptor radius r, defined as the distance between the aromatic π-systems of the two emitters, being greater than 8 Å.

### Claim 13

A consumer product comprising an OLED comprising:
an anode;
a cathode; and
a first organic layer disposed between the anode and the cathode;
wherein the first organic layer comprises a primary phosphorescent emitter and a first host;
wherein one of the following conditions is true:
(1) the first organic layer further comprises a secondary emitter; or
(2) the OLED device further comprises a second organic layer disposed between the anode and the cathode, wherein the second organic layer comprises a secondary emitter;
wherein the primary phosphorescent emitter has a formula of M1(LA)x(LB)y(LC)z;
wherein LA, LB and LC are each a bidentate ligand;
wherein M1 is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; and
wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M1;
wherein LA is selected from the group consisting of:
LB and LC are each independently selected from the group consisting of:
wherein,
each X1 to X10 are independently selected from the group consisting of C and N;
at least one of X1 to X10 is N;
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″;
R′ and R″ are optionally fused or joined to form a ring;
each Ra, Rb, and Rc represents from mono substitution to the maximum possible number of substitutions, or no substitution;
R′, R″, Ra, Rb, and Rc are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, benzonitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two adjacent substituents of Ra, Rb, and Rc can be fused or joined to form a ring or form a multidentate ligand;
wherein the primary phosphorescent emitter has a peak emission wavelength λmax that is ≥600 nm and ≤750 nm;
wherein the secondary emitter is a near-infrared emitter that has a peak emission wavelength λmax that is between 750 nm and 2500 nm; and wherein the first host has a lowest excited state triplet energy T1 that is at least 0.1 eV higher than that of the primary phosphorescent emitter,
wherein the secondary emitter is selected from the group consisting of: a fluorescent emitter, a thermally activated delayed fluorescence emitter, and an emitter containing an unpaired electron in its ground state,
whereby Dexter energy transfer from the primary emitter to the secondary emitter is minimized to prevent formation of fluorophore triplet excitons,
wherein the consumer product is one 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 OLED, 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, a light therapy device, or a sign.