# US 9,518,063 B2 · Organic electroluminescent materials and devices

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- Number: US 9,518,063 B2
- Document ID: US9518063B2
- Status: Granted
- Kind: B2
- Application number: 14/735,589
- Filed: 2015-06-10
- Published: 2015-10-01
- Granted: 2016-12-13
- Earliest claimed: 2009-01-16
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Chun Lin; Bin Ma; Raymond Kwong; Alexey Borisovich Dyatkin; Yonggang Wu; Zeinab M. Elshenawy
- Web page: https://patentgrep.com/patent/US9518063B2

## CPC

- C07D 491/04: Ortho-condensed systems
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H05B 33/20: characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/155: comprising dopants
- H10K 50/156: {comprising a multilayered structure}
- H10K 50/157: {between the light-emitting layer and the cathode}
- H10K 50/171: {Electron injection layers}
- H10K 59/32: Stacked devices having two or more layers, each emitting at different wavelengths
- H10K 85/342: {comprising iridium}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/17: Carrier injection layers
- H10K 50/18: Carrier blocking layers
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A new class of compounds containing aza-dibenzothiophene or aza-dibenzofuran are provided. The compounds may be used in organic light emitting devices giving improved stability, improved efficiency, long lifetime and low operational voltage. In particular, the compounds may be used as the host material of an emissive layer having a host and an emissive dopant, or as a material in an enhancement layer.

## Claims

### Claim 1

A process comprising:
treating an acetic acid solution of an intermediate having the formula
wherein one of X1 and X2 is nitrogen and the other of X1 and X2 is carbon and wherein Y is S or O, with tBuONO to produce an aza complex having the formula
wherein R1 and R2 may represent mono, di, tri, or tetra substitutions;
wherein R1 is selected from the group consisting of hydrogen, alkyl, aryl, heteroaryl and halide; and
wherein R2 is selected from the group consisting of hydrogen, alkyl, aryl and halide.

### Claim 2 (depends on 1)

The process of claim 1, wherein Y is S.

### Claim 3 (depends on 1)

The process of claim 1, wherein Y is O.

### Claim 4 (depends on 1)

The process of claim 1, wherein X1 is nitrogen and X2 is carbon.

### Claim 5 (depends on 1)

The process of claim 1, wherein X1 is carbon and X2 is nitrogen.

### Claim 6 (depends on 1)

The process of claim 1, wherein R1 is halide.

### Claim 7 (depends on 1)

The process of claim 1, wherein R2 includes at least one halide.

### Claim 8 (depends on 1)

The process of claim 1, wherein R2 includes only halide substituents.

### Claim 9 (depends on 1)

The process of claim 1, wherein R2 is not halide, Y is S, and the amino-arylthio pyridine intermediate is treated with H2SO4 prior to treatment with tBuONO.

### Claim 10 (depends on 1)

The process of claim 1, wherein Y is S and the yield of
is greater than 50%.