# US 10,870,668 B2 · Organic electroluminescent materials and devices

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- Number: US 10,870,668 B2
- Document ID: US10870668B2
- Status: Granted
- Kind: B2
- Application number: 15/948,433
- Filed: 2018-04-09
- Published: 2018-11-08
- Granted: 2020-12-22
- Earliest claimed: 2017-05-05
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Zhiqiang Ji; Chun Lin; Jui-Yi Tsai
- Web page: https://patentgrep.com/patent/US10870668B2

## CPC

- C07F 15/0033: {Iridium compounds}
- C07F 15/0086: {Platinum compounds}
- H10K 50/12: comprising dopants
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 85/342: {comprising iridium}
- H10K 85/344: {comprising ruthenium}
- H10K 85/346: {comprising platinum}
- H10K 85/348: {comprising osmium}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A compound comprising a first ligand LA having the formula Formula I, is disclosed. In Formula I, ring A is a five- or six-membered carbocyclic or heterocyclic ring; Y1 is selected from carbon and nitrogen; each of X1 to X4 is C or N; at least two adjacent R2s of ring B form a fused structure having the following formula: ring C is fused to ring B and the wavy lines are bonds attached to ring B; ring D and ring E are either a 5-membered aromatic ring or a 6-membered aromatic ring; each R1, R2, R3, RA, RB, RC, and RD is independently selected from a variety of substituents; ligand LA is coordinated to a metal M and, optionally, linked with other ligands; and M is optionally coordinated to other ligands. Organic light emitting devices and consumer products containing the compounds are also disclosed.

## Claims

### Claim 1

A compound comprising a first ligand LA having the formula:
Formula I;
wherein ring A is a five- or six-membered carbocyclic or heterocyclic ring;
wherein Y1 is selected from the group consisting of carbon and nitrogen;
wherein X1 to X4 are each independently a C or N;
wherein R1 represents from no substitution up to a maximum possible number of substitutions;
wherein R2 represents from two substitutions up to a maximum possible number of substitutions;
wherein at least two adjacent R2s of ring B form a fused structure having the following formula:
wherein ring C is fused to ring B and the wavy lines are bonds attached to ring B;
wherein ring D and ring E are each independently a 5-membered aromatic ring or a 6-membered aromatic ring;
wherein ring D is fused to ring C, and ring E is fused to ring D;
wherein R3 represents from no substitution up to a maximum possible number of substitutions;
wherein each R1, R2, R3, RA, RB, RC, and RD is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any substituents are optionally joined to form into a ring;
wherein the ligand LA is coordinated to a metal M;
wherein LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.

### 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 ring D and ring E are benzene.

### Claim 4 (depends on 1)

The compound of claim 1, wherein one of ring D and ring E is benzene and the other one of ring D and ring E is pyridine.

### Claim 5 (depends on 1)

The compound of claim 1, wherein ring A is selected from the group consisting of pyridine, pyrimidine, imidazole, pyrazole, and imidazole derived carbene.

### Claim 6 (depends on 1)

The compound of claim 1, wherein each R1, R2, R3, RA, RB, RC, and RD is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the ligand LA is selected from the group consisting of:
wherein X5 to X18 are each independently selected from the group consisting of nitrogen and carbon;
wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, CR′R″, and NR′;
wherein RE, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any substituents are optionally joined to form into a ring.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the ligand LA is selected from the group consisting of:
LA231 to LA235 having the following structure:
wherein, in LA231, Y═O;
in LA232, Y═S;
in LA233, Y═C(CH3)2;
in LA234, Y═Se; and
in LA235, Y═N(CH3);
LA236 to LA240 having the following structure:
wherein, in LA236, Y═O;
in LA237, Y═S;
in LA238, Y═C(CH3)2;
in LA239, Y═Se; and
in LA240, Y═N(CH3);
LA241 to LA245 having the following structure:
wherein, in LA241, Y═O;
in LA242, Y═S;
in LA243, Y═C(CH3)2;
in LA244, Y═Se; and
in LA245, Y═N(CH3);
LA246 to LA250 having the following structure:
wherein, in LA246, Y═O;
in LA247, Y═S;
in LA248, Y═C(CH3)2;
in LA249, Y═Se; and
in LA250, Y═N(CH3);
LA251 to LA255 having the following structure:
wherein, in LA251, Y═O;
in LA252, Y═S;
in LA253, Y═C(CH3)2;
in LA254, Y═Se; and
in LA255, Y═N(CH3),
LA256 to LA260 having the following structure:
wherein, in LA256, Y═O;
in LA257, Y═S;
in LA258, Y═C(CH3)2;
in LA259, Y═Se; and
in LA260, Y═N(CH3),
and

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound has a formula of M(LA)x(LB)y(LC)z;
wherein LB and LC are each a bidentate ligand; and
wherein x is 1, 2, or 3; y is 1 or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.

### Claim 10 (depends on 9)

The compound of claim 9, wherein the compound has a formula selected from the group consisting of Ir(LA)3, Ir(LA)(LB)2, Ir(LA)2(LB), and Ir(LA)(LB)(LC); and
wherein LA, LB, and LC are different from each other.

### Claim 11 (depends on 9)

The compound of claim 9, wherein the compound has a formula of Pt(LA)(LB); and wherein LA and LB can be same or different.

### Claim 12 (depends on 9)

The compound of claim 9, wherein LB and LC are each independently selected from the group consisting of:
wherein each Y1 to Y13 is 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 represents from mono substitution to a maximum possible number of substitutions, or no substitution;
wherein each of R′, R″, Ra, Rb, Rc, and Rd is 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 13 (depends on 8)

The compound of claim 8, wherein the compound is selected from the group consisting of Compound x having the formula Ir(LAi)(LBk)2;
wherein x is an integer defined by x=3001+k−300; wherein i is an integer from 1 to 260, and k is an integer from 1 to 300; and
wherein LB1 through LB300 have the following structures:

### Claim 14

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 the formula:
Formula I;
wherein ring A is a five- or six-membered carbocyclic or heterocyclic ring;
wherein Y1 is selected from the group consisting of carbon and nitrogen;
wherein X1 to X4 are each independently a C or N;
wherein R1 represents from no substitution up to a maximum possible number of substitutions;
wherein R2 represents from two substitutions up to a maximum possible number of substitutions;
wherein at least two adjacent R2s of ring B form a fused structure having the following formula:
wherein ring C is fused to ring B and the wavy lines are bonds attached to ring B;
wherein ring D and ring E are each independently a 5-membered aromatic ring or a 6-membered aromatic ring;
wherein ring D is fused to ring C, and ring E is fused to ring D;
wherein R3 represents from no substitution up to a maximum possible number of substitutions;
wherein each R1, R2, R3, RA, RB, RC, and RD is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any substituents are optionally joined to form into a ring;
wherein the ligand LA is coordinated to a metal M;
wherein LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.

### Claim 15 (depends on 14)

The OLED of claim 14, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

### Claim 16 (depends on 14)

The OLED of claim 14, wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

### Claim 17 (depends on 14)

The OLED of claim 14, wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
and combinations thereof.

### Claim 18

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 comprising a first ligand LA having the formula:
Formula I;
wherein ring A is a five- or six-membered carbocyclic or heterocyclic ring;
wherein Y1 is selected from the group consisting of carbon and nitrogen;
wherein X1 to X4 are each independently a C or N;
wherein R1 represents from no substitution up to a maximum possible number of substitutions;
wherein R2 represents from two substitutions up to a maximum possible number of substitutions;
wherein at least two adjacent R2s of ring B form a fused structure having the following formula:
wherein ring C is fused to ring B and the wavy lines are bonds attached to ring B;
wherein ring D and ring E are each independently a 5-membered aromatic ring or a 6-membered aromatic ring;
wherein ring D is fused to ring C, and ring E is fused to ring D;
wherein R3 represents from no substitution up to a maximum possible number of substitutions;
wherein each R1, R2, R3, RA, RB, RC, and RD is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any substituents are optionally joined to form into a ring;
wherein the ligand LA is coordinated to a metal M;
wherein LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.

### Claim 19 (depends on 18)

The consumer product of claim 18, 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 that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video walls comprising multiple displays tiled together, a theater or stadium screen, and a sign.

### Claim 20 (depends on 1)

A formulation comprising the compound of claim 1.