# US 10,121,975 B2 · Organic electroluminescent materials and devices

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- Number: US 10,121,975 B2
- Document ID: US10121975B2
- Status: Granted
- Kind: B2
- Application number: 14/302,042
- Filed: 2014-06-11
- Published: 2015-01-08
- Granted: 2018-11-06
- Earliest claimed: 2013-07-03
- Assignees: Universal Display Corporation
- Applicants: University of Southern California
- Inventors: Mark E. Thompson; Yifei Liu; Peter I. Djurovich
- Web page: https://patentgrep.com/patent/US10121975B2

## CPC

- H10K 85/342: {comprising iridium}
- C07F 15/0033: {Iridium compounds}
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1096: containing other heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A compound comprising a ligand LA selected from: as well as, devices and formulations containing the compound are disclosed. In the compounds, independently X1-X6 are CH or N; Y1-Y12 are independently selected from CH, N, and C-APR1′R1″; when present, exactly one of Y1 through Y12 is C-APR1′R1″ in LA8; A is selected from a single bond, —CRARB—, —NRA—, —O—, —S— and —SiRARB—; and R, R1′, R1″, R2, R3, RA, and RB are each independently a substituent selected from hydrogen, deuterium, alkyl, cycloalkyl, aryl, and combinations thereof. The P-atom of the ligand LA is bonded to a metal M having an atomic weight of at least 40.

## Claims

### Claim 1

A compound comprising a metal and a ligand LA selected from the group of ligands consisting of:
wherein Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, and Y12 are independently selected from the group consisting of CH, C bonded to metal M, N, and C-APR1′R1″, and the ligand LA is bidentate with a first bond to the metal M formed with the P-atom of the C-APR1′R1″ and a second bond to the metal M formed with a ring carbon of ligand LA5, ligand LA6, ligand LA7, or ligand LA8; wherein the metal M has an atomic weight of at least 40;
wherein exactly one of Y1 through Y8 is C-APR1′R1″ in LA5 and LA6, and exactly one of Y1 through Y8 is the ring carbon bonded to the metal;
wherein exactly one of Y1 through Y10 is C-APR1′R1″ in LA7, and exactly one of Y1 through Y10 is the ring carbon bonded to the metal;
wherein exactly one of Y1 through Y12 is C-APR1′R1″ in LA8, and exactly one of Y1 through Y12 is the ring carbon bonded to the metal;
wherein A is selected from the group consisting of a single bond, —CRARB—, —NRA—, —O—, —S— and —SiRARB—;
wherein R, R1′, R1″, R2, R3, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and aryl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein M is a metal 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 R1′ and R1″ are each phenyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound has the formula M(LA)m(LB)n, wherein the ligand LB is a different ligand from the ligand LA;
wherein m is an integer from 1 to the maximum number of ligands that may be coordinated to the metal M; and m+n is the maximum number of ligands that may be coordinated to the metal M, and the ligand LB is selected from the group of ligands consisting of:
wherein:
X7, X8, X9, and X10 are independently selected from the group consisting of CH, and N;
X11, X12, and X13 are independently selected from the group consisting of CH, CR′, and N;
Ra, Rb, and Rc, may represent mono, di, tri, or tetra substitution, or no substitution;
Rd may represent mono, di, or tri substitution, or no substitution;
R′, Ra, Rb, Rc, Rd are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carboxylic acids, ester, nitrile, isonitrile, and phosphino; and
two adjacent substituents of Ra, Rb, Rc, and Rd are optionally joined to form a fused ring;
wherein dotted arcs of ligand LB28 and ligand LB29 represent optional fused rings, which can be cyclic, heterocyclic, aromatic, or heteroaromatic, and which can be further substituted; and
if present, each end of each dotted arc is fused to a carbon atom.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound is homoleptic.

### Claim 7 (depends on 6)

The compound of claim 6, wherein the compound has a facial configuration.

### Claim 8 (depends on 6)

The compound of claim 6, wherein the compound has a meridional configuration.

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 9)

The compound of claim 9, wherein the second bond between the metal and the ligand LA is formed by:
a carbon atom of Ring 2 of the ligands LA5-1 and LA6-1.

### Claim 11 (depends on 1)

The compound of claim 1, wherein the compound has the formula M(LA)m(LB)n, wherein the ligand LB is a different ligand from the ligand LA;
wherein m is an integer from 1 to the maximum number of ligands that may be coordinated to the metal M; and m+n is the maximum number of ligands that may be coordinated to the metal M, and the ligand LB is selected from the group of ligands consisting of:
wherein:
X7, X8, X9, and X10 are independently selected from the group consisting of CH, and N;
X11, X12, and X13 are independently selected from the group consisting of CH, CR′, and N;
Ra, Rb, and Rc, may represent mono, di, tri, or tetra substitution, or no substitution;
R′, Ra, Rb, and Rc are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carboxylic acids, ester, nitrile, isonitrile, and phosphino; and
two adjacent substituents of Ra, Rb, and Rc are optionally joined to form a fused ring;
wherein dotted arcs of ligand LB29 represent optional fused rings, which can be cyclic, heterocyclic, aromatic, or heteroaromatic, and which can be further substituted; and
if present, each end of each dotted arc is fused to a carbon atom.

### Claim 12 (depends on 11)

The compound of claim 11, where the compound is selected from the group consisting of:
wherein
is selected from the group consisting of LB1 through LB10, LB12 through LB25, and LB29,
wherein each R1 is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and aryl, and
wherein n=0, 1, or 2.

### Claim 13

A first device comprising an organic light emitting device, the organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising a metal and a ligand LA selected from the group of ligands consisting of:
wherein Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, and Y12 are independently selected from the group consisting of CH, C bonded to metal M, N, and C-APR1′R1″, and the ligand LA is bidentate with a first bond to the metal M formed with the P-atom of the C-APR1′R1″ and a second bond to the metal M formed with a ring carbon of ligand LA5, ligand LA6, ligand LA7, or ligand LA8; wherein the metal M has an atomic weight of at least 40;
wherein exactly one of Y1 through Y8 is C-APR1′R1″ in LA5 and LA6, and exactly one of Y1 through Y8 is the ring carbon bonded to the metal;
wherein exactly one of Y1 through Y10 is C-APR1′R1″ in LA7, and exactly one of Y1 through Y10 is the ring carbon bonded to the metal;
wherein exactly one of Y1 through Y12 is C-APR1′R1″ in LA8, and exactly one of Y1 through Y12 is the ring carbon bonded to the metal;
wherein A is selected from the group consisting of a single bond, —CRARB—, —NRA—, —O—, —S— and —SiRARB—;
wherein R, R1′, R1″, R2, R3, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and aryl.

### Claim 14 (depends on 13)

The first device of claim 13, wherein the first device is a consumer product.

### Claim 15 (depends on 13)

The first device of claim 13, wherein the first device is an organic light-emitting device.

### Claim 16 (depends on 13)

The first device of claim 13, wherein the first device comprises a lighting panel.

### Claim 17 (depends on 13)

The first device of claim 13, wherein the organic layer is an emissive layer comprising a host and the compound is a non-emissive dopant.

### Claim 18 (depends on 13)

The first device of claim 13, wherein the organic layer further comprises a host, and the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of CmH2m+1, OCmH2m+1, OAr1, N(CmH2m+1)2, N(Ar1)(Ar2), CH═CH—CmH2m+1, C═CCmH2m+1, Ar1, Ar1-Ar2, and CmH2m—Ar1;
wherein m is from 1 to 10; and
wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

### Claim 19 (depends on 13)

The first device of claim 13, wherein the organic layer further comprises a host, and the host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

### Claim 20 (depends on 13)

The first device of claim 13, wherein the organic layer further comprises a host, and the host is selected from the group consisting of:
and combinations thereof.

### Claim 21

A formulation comprising a compound comprising a metal and a ligand LA selected from the group of ligands consisting of:
wherein Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, and Y12 are independently selected from the group consisting of CH, C bonded to metal M, N, and C-APR1′R1″, and the ligand LA is bidentate with a first bond to the metal M formed with the P-atom of the C-APR1′R1″ and a second bond to the metal M formed with a ring carbon of ligand LA5, ligand LA6, ligand LA7, or ligand LA8;
wherein the metal M has an atomic weight of at least 40;
wherein exactly one of Y1 through Y8 is C-APR1′R1″ in LA5, and LA6, and exactly one of Y1 through Y8 is the ring carbon bonded to the metal;
wherein exactly one of Y1 through Y10 is C-APR1′R1″ in LA7, and exactly one of Y1 through Y10 is the ring carbon bonded to the metal;
wherein exactly one of Y1 through Y12 is C-APR1′R1″ in LA8, and exactly one of Y1 through Y12 is the ring carbon bonded to the metal;
wherein A is selected from the group consisting of a single bond, —CRARB—, —NRA—, —O—, —S— and —SiRARB—;
wherein R, R1′, R1″, R2, R3, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and aryl.