# US 10,312,458 B2 · Organic electroluminescent materials and devices

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- Number: US 10,312,458 B2
- Document ID: US10312458B2
- Status: Granted
- Kind: B2
- Application number: 14/875,147
- Filed: 2015-10-05
- Published: 2016-04-07
- Granted: 2019-06-04
- Earliest claimed: 2009-03-23
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Gregg Kottas; Nasrin Ansari; Zeinab Elshenawy; Alan DeAngelis; Chuanjun Xia
- Web page: https://patentgrep.com/patent/US10312458B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 15/0033: {Iridium compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- 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 85/342: {comprising iridium}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/624: {containing six or more rings}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- 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 2211/1088: containing oxygen as the only heteroatom
- 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 50/12: comprising dopants
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

## Claims

### Claim 1

A compound having the formula:
wherein R1 and R2 are optionally linked;
wherein R1 and R2 are independently selected from the group consisting of hydrogen, deuterium, partially or fully deuterated alkyl, partially or fully deuterated cycloalkyl, and combinations thereof;
wherein the sum of the number of carbon atoms in R1 and R2 is at least 2;
wherein R3, R4, R5, R6 are optionally linked;
wherein Ra and Rb represent mono-, di-, tri- or tetra-substitution;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, S═O, SO2, SiRR′, and GeRR′;
wherein Ra, Rb, R, R′, R3, R4, R5, and R6 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein the compound is heteroleptic; and
wherein n is 1 or 2.

### Claim 2 (depends on 1)

The compound of claim 1, wherein X is O.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 is hydrogen and R2 is selected from the group consisting of partially or fully deuterated alkyl, partially or fully deuterated cycloalkyl, and combinations thereof.

### Claim 4

A compound having the formula:
wherein the sum of the number of carbon atoms in R1 is at least 2;
wherein R3, R4, R5, R6 are optionally linked;
wherein Ra and Rb represent mono-, di-, tri- or tetra-substitution;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein Ra, Rb, R, R′, R3, R4, R5, and R6 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, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein n is 1 or 2, and
wherein R1 is selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variations thereof, and combinations thereof and R2 is hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R1 and R2 are partially or fully deuterated alkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R1 or R2 are independently selected from the group consisting of partially or fully deuterated branched alkyl, partially or fully deuterated cyclic alkyl, partially or fully deuterated bicyclic alkyl, and partially or fully deuterated multicyclic alkyl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R1 or R2 is partially or fully deuterated iso-propyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R3, R4, R5 and R6 are independently selected from the group consisting of hydrogen, deuterium, alkyl, arylalkyl, and combinations thereof.

### Claim 9 (depends on 1)

The compound of claim 1, wherein at least one of R3, R4, R5 and R6 comprises a branched alkyl, cyclic alkyl, bicyclic alkyl, a multicyclic alkyl, or a partially or fully deuterated variant thereof.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R3, R4, R5 or R6 contain one or more deuterium atoms.

### Claim 11

A first device comprising a first organic light emitting device, comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:
wherein R1 and R2 are optionally linked;
wherein R1 and R2 are independently selected from the group consisting of hydrogen, deuterium, partially or fully deuterate alkyl, partially or fully deuterated cycloalkyl, and combinations thereof;
wherein the sum of the number of carbon atoms in R1 and R2 is at least 2;
wherein R3, R4, R5, R6 are optionally linked;
wherein Ra and Rb represent mono-, di-, tri- or tetra-substitution;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, S═O, SO2, SiRR′, and GeRR′;
wherein Ra, Rb, R, R′, R3, R4, R5, and R6 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein the compound is heteroleptic; and
wherein n is 1 or 2.

### Claim 12 (depends on 11)

The first device of claim 11, wherein the first device is selected from the group consisting of a consumer product, an organic light-emitting device, a lighting panel, and a combination thereof.

### Claim 13 (depends on 11)

The first device of claim 11, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

### Claim 14 (depends on 11)

The first device of claim 11, wherein the organic layer 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 CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡CCnH2n+1, Ar1, Ar1—Ar2, CnH2n—Ar1;
wherein n 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 15 (depends on 14)

The first device of claim 14, wherein the host has the formula:

### Claim 16 (depends on 11)

The first device of claim 11, wherein the organic layer comprises a host, and the host is selected from the group consisting of:
and combinations thereof.

### Claim 17 (depends on 1)

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

### Claim 18 (depends on 4)

The compound of claim 4, wherein the compound is selected from the group consisting of: