# US 10,374,173 B2 · Organic electroluminescent materials and devices

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- Number: US 10,374,173 B2
- Document ID: US10374173B2
- Status: Granted
- Kind: B2
- Application number: 15/452,994
- Filed: 2017-03-08
- Published: 2017-06-22
- Granted: 2019-08-06
- Earliest claimed: 2009-04-28
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Chuanjun Xia; James Fiordeliso; Raymond Kwong
- Web page: https://patentgrep.com/patent/US10374173B2

## CPC

- H10K 85/342: {comprising iridium}
- C07F 15/0033: {Iridium compounds}
- C07F 15/0086: {Platinum compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 85/346: {comprising platinum}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as 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
- Y02E 10/549: Organic PV cells
- 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
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Novel organic compounds comprising ligands with deuterium substitution are provided. In particular, the compound is an iridium complex comprising methyl-d3 substituted ligands. The compounds may be used in organic light emitting devices to provide devices having improved color, efficiency and lifetime.

## Claims

### Claim 1

A compound comprising a ligand having the structure:
wherein A and B may independently represent a 5-membered or 6-membered aromatic ring;
wherein A1, A2, B1, and B2 are independently C or N;
wherein RA and RB may represent mono, di, or tri substitutions;
wherein XA and XB are independently C or a heteroatom;
wherein RA, RB, R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl;
wherein at least one of RA, RB, R1 and R2 includes CD, CD2 or CD3, wherein the deuterium atoms are provided within an alkyl chain or at the end of an alkyl chain;
wherein RA, RB, R1 and R2 may be linked;
wherein RA, RB, R1 and R2 may be fused;
wherein the ligand is coordinated to Pt; and
at least one of the following is true:
(i) ring A is a 5-membered aromatic ring and A2=N,
(ii) ring A is a 6-membered ring, A2=N, and R1 and RA are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl,
(iii) A2=N, XA=N, and R1 is aryl, and
(iv) R1 and R2 are linked or fused to each other.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the ligand has the structure:

### Claim 3 (depends on 2)

The compound of claim 2, wherein at least one of RA, RB, R1 and R2 includes CD3.

### Claim 4 (depends on 1)

The compound of claim 1, wherein at least one of the substituents of RA and RB is CD3 attached directly to ring A, ring B, or a ring that is conjugated or fused to ring A or ring B.

### Claim 5 (depends on 1)

The compound of claim 1, wherein XA and XB are independently C or N and when XA is N, R1 is aryl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein XA and XB are independently C or N and when XA is N, R1 is phenyl further substituted with a substituent selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl and wherein the substituent includes at least one of CD, CD2 or CD3.

### Claim 7 (depends on 1)

The compound of claim 1, wherein A is selected from the group consisting of imidazole, pyrazole, triazole, oxazole, oxadiazole, pyridine, pyridazine, pyrimidine, pyrazine, and triazine.

### Claim 8 (depends on 1)

The compound of claim 1, wherein B is selected from the group consisting of benzene, pyridine, furan, pyrrole, and thiophene.

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is a heteroleptic compound.

### Claim 11

An organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand having the structure:
wherein A and B may independently represent a 5-membered or 6-membered aromatic ring;
wherein A1, A2, B1, and B2 are independently C or N;
wherein RA and RB may represent mono, di, or tri substitutions;
wherein XA and XB are independently C or a heteroatom;
wherein RA, RB, R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl;
wherein at least one of RA, RB, R1 and R2 includes CD, CD2 or CD3, wherein the deuterium atoms are provided within an alkyl chain or at the end of an alkyl chain;
wherein RA, RB, R1 and R2 may be linked;
wherein RA, RB, R1 and R2 may be fused;
wherein the ligand is coordinated to Pt; and
at least one of the following is true:
(i) ring A is a 5-membered aromatic ring and A2=N,
(ii) ring A is a 6-membered ring, A2=N, and R1 and RA are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl,
(iii) A2=N, XA=N, and R1 is aryl, and
(iv) R1 and R2 are linked or fused to each other.

### Claim 12 (depends on 11)

The device of claim 11, wherein the organic layer is an emissive layer and the compound is an emitting dopant.

### Claim 13 (depends on 12)

The device of claim 12, wherein the organic layer further comprises a host.

### Claim 14

A consumer product comprising a device, the device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand having the structure:
wherein A and B may independently represent a 5-membered or 6-membered aromatic ring;
wherein A1, A2, B1, and B2 are independently C or N;
wherein RA and RB may represent mono, di, or tri substitutions;
wherein XA and XB are independently C or a heteroatom;
wherein RA, RB, R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl;
wherein at least one of RA, RB, R1 and R2 includes CD, CD2 or CD3, wherein the deuterium atoms are provided within an alkyl chain or at the end of an alkyl chain;
wherein RA, RB, R1 and R2 may be linked;
wherein RA, RB, R1 and R2 may be fused;
wherein the ligand is coordinated to Pt; and
at least one of the following is true:
(i) ring A is a 5-membered aromatic ring and A2=N,
(ii) ring A is a 6-membered ring, A2=N, and R1 and RA are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl,
(iii) A2=N, XA=N, and R1 is aryl, and
(iv) R1 and R2 are linked or fused to each other.

### Claim 15 (depends on 14)

The consumer product of claim 14, wherein the consumer product is selected from the group consisting of flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, vehicles, a wall, theater or stadium screen, and a sign.

### Claim 16 (depends on 1)

The compound of claim 1, wherein ring A is 5-membered aromatic ring and A2=N.

### Claim 17 (depends on 1)

The compound of claim 1, wherein ring A is a 6-membered ring,
wherein A2=N; and
wherein R1 and RA are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl.

### Claim 18 (depends on 1)

The compound of claim 1, wherein A2=N, XA=N, and R1 is aryl.

### Claim 19 (depends on 1)

The compound of claim 1, wherein R1 and R2 are linked or fused to each other.