# US 12,180,230 B2 · Carbene compounds and organic electroluminescent devices

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- Number: US 12,180,230 B2
- Document ID: US12180230B2
- Status: Granted
- Kind: B2
- Application number: 16/191,604
- Filed: 2018-11-15
- Published: 2019-05-30
- Granted: 2024-12-31
- Earliest claimed: 2017-11-28
- Assignees: University of Southern California
- Applicants: University of Southern California
- Inventors: Mark E. Thompson; Peter I. Djurovich; Rasha Hamze; Shuyang Shi; Moon Chul Jung
- Web page: https://patentgrep.com/patent/US12180230B2

## CPC

- C07F 1/10: Silver compounds
- C07F 1/08: Copper compounds
- C07F 1/12: Gold compounds
- C09B 57/10: Metal complexes of organic compounds not being dyes in uncomplexed form
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/371: {Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver}
- H10K 2101/10: Triplet emission
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A compound selected from the group consisting of Formula I, Formula II, and Formula III, wherein ring A, ring B, and ring C are independently a five-membered or six-membered, carbocyclic or heterocyclic ring, each of which is optionally aromatic; ring W of Formula I is a 6-membered heterocyclic ring, and ring W of Formula II or Formula III is a 5-membered or 6-membered heterocyclic ring; L is a monodentate ligand with a metal coordinating member selected from the group consisting of C, N, O, S, and P; and M is a metal selected from the group consisting of Cu, Au, and Ag.

## Claims

### Claim 1

A compound selected from the group consisting of Formula I and Formula III,
wherein
L is a monodentate anionic ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
M is a metal selected from the group consisting of Cu, Au, and Ag;
each of R1 and R2 is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, cycloalkenyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; each of which is optionally substituted;
wherein R1 and R2 are further joined to form a single carbocyclic ring with an optional heteroatom, wherein the carbocyclic ring does not include an unsubstituted cyclohexyl ring or an adamantyl ring;
each of RA and RB independently represent mono to the maximum allowable substitution, or no substitution, and
each RA and RB is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
or optionally, any two adjacent RA or RB can join to form a ring, which is optionally substituted;
one of Y1 and Y2 is C═O and the other of Y1 and Y2 is CRR′ or C═O, wherein R and R′ are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof, or optionally, R and R′ can be joined to form a ring, which is optionally substituted;
L is selected from the group consisting of: NRXRY, PRXRY, CRXRYRZ, phenyl, substituted phenyl, ORX, and SRX,
wherein RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, each of which is optionally substituted, or optionally, RX and RY can join to form five-membered or six-membered, carbocyclic or heterocyclic ring, which is optionally substituted; and
wherein in Formula I, when L is a substituted phenyl, the substitution is not two methyl groups at both ortho positions, and
in Formula III, when L is ORX, RX is not butyl; and when L is CRXRYRZ, RX, RY, and RZ are not methyl.

### Claim 2 (depends on 1)

The compound of claim 1, selected from the group consisting of Formula 1A and Formula 1B

### Claim 3 (depends on 1)

The compound of claim 1, wherein L is NRXRY and is selected from the group consisting of:
an optionally substituted carbazolyl, or an aza-derivative thereof;
an optionally substituted diphenylamino, or an aza-derivative thereof,
wherein RX′, RY′, and RN are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof; and
Rk and Rl are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, and combinations thereof.

### Claim 4 (depends on 1)

The compound of claim 1, wherein RX and/or RY is selected from the group consisting of:
an aryl, optionally substituted with deuterium, alkyl, or an electron donating substituent group,
a heteroaryl, optionally substituted with deuterium, alkyl, or an electron donating substituent group, and
an alkyl, optionally substituted with one or more deuterium atoms.

### Claim 5 (depends on 1)

The compound of claim 1 with an emission lifetime of 0.05 μs to 10 μs, as measured as a polystyrene film at 23° C.

### Claim 6 (depends on 1)

The compound of claim 1 with an energy separation (ΔE) of the lowest excited singlet state and triplet states is from 10 meV and 150 meV as determined by temperature dependent emission lifetime measurement.

### Claim 7 (depends on 1)

The compound of claim 1, with an emission spectra spanning from 390 nm to 850 nm as measured as a polystyrene film at 23° C.

### Claim 8 (depends on 1)

The compound of claim 1, with maximum emission wavelength (λmax) of from 432 nm to 666 nm as measured as a polystyrene film at 23° C.

### Claim 9 (depends on 1)

The compound of claim 1 being an E-type delayed fluorescent emitter.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the metal is Au(I).

### Claim 11

An organic electroluminescent device (OLED) that includes an anode, a cathode, and an organic layer comprising a compound selected from the group consisting of Formula I and Formula III,
wherein
L is a monodentate anionic ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
M is a metal selected from the group consisting of Cu, Au, and Ag;
each of R1 and R2 is independently selected from the group consisting of hydrogen,
deuterium, fluorine, alkyl, cycloalkyl, cycloalkenyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; each of which is optionally substituted;
wherein R1 and R2 are further joined to form a single carbocyclic ring with an optional heteroatom, wherein the carbocyclic ring does not include an unsubstituted cyclohexyl ring or an adamantyl ring;
each of RA and RB independently represent mono to the maximum allowable substitution, or no substitution, and
each RA and RB is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
or optionally, any two adjacent RA or RB can join to form a ring, which is optionally substituted;
one of Y1 and Y2 is C═O and the other of Y1 and Y2 is CRR′ or C═O, wherein R and R′ are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof, or optionally, R and R′ can be joined to form a ring, which is optionally substituted;
L is selected from the group consisting of: NRXRY, PRXRY, CRXRYRZ, phenyl, substituted phenyl, ORX, and SRX,
wherein RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; each of which is optionally substituted, or optionally, RX and RY can join to form five-membered or six-membered, carbocyclic or heterocyclic ring, which is optionally substituted; and
wherein in Formula I, when L is a substituted phenyl, the substitution is not two methyl groups at both ortho positions, and in Formula III, when L is ORX, RX is not butyl; and when L is CRXRYRZ, RX, RY, and RZ are not methyl.

### Claim 12 (depends on 11)

The OLED of claim 11, wherein the device emits a luminescent radiation at room temperature when a voltage is applied across the organic light emitting device, and the luminescent radiation comprises a first radiation component that arises from a delayed fluorescent process or triplet exciton harvesting process.

### Claim 13 (depends on 11)

The OLED of claim 11, wherein the organic layer further comprises a host, wherein the 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 14 (depends on 11)

The OLED of claim 11, wherein the OLED further comprises a host, and the host is selected from the group consisting of:
and combinations thereof.

### Claim 15

A consumer product comprising an organic light-emitting device (OLED), the OLED including an anode, a cathode, and an organic layer comprising a compound selected from the group consisting of Formula I and Formula III,
wherein
L is a monodentate anionic ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
M is a metal selected from the group consisting of Cu, Au, and Ag;
each of R1 and R2 is independently selected from the group consisting of hydrogen,
deuterium, fluorine, alkyl, cycloalkyl, cycloalkenyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; each of which is optionally substituted;
wherein R1 and R2 are further joined to form a single carbocyclic ring with an optional heteroatom, wherein the carbocyclic ring does not include an unsubstituted cyclohexyl ring or an adamantyl ring;
each of RA and RB independently represent mono to the maximum allowable substitution, or no substitution, and
each RA and RB is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
or optionally, any two adjacent RA or RB can join to form a ring, which is optionally substituted;
one of Y1 and Y2 is C═O and the other of Y1 and Y2 is CRR′ or C═O, wherein R and R′ are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof, or optionally, R and R′ can be joined to form a ring, which is optionally substituted;
L is selected from the group consisting of: NRXRY, PRXRY, CRXRYRZ, phenyl, substituted phenyl, ORX, and SRX,
wherein RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; each of which is optionally substituted, or optionally, RX and RY can join to form five-membered or six-membered, carbocyclic or heterocyclic ring, which is optionally substituted; and
wherein in Formula I, when L is a substituted phenyl, the substitution is not two methyl groups at both ortho positions, and in Formula III, when L is ORX, RX is not butyl; and when L is CRXRYRZ, RX, RY, and RZ are not methyl;
wherein the compounds of Formula I and Formula III are vapor deposited with a host material to provide the organic layer; and
wherein the consumer product is selected from the group consisting 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, 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, and a sign.

### Claim 16 (depends on 1)

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