Organic electroluminescent materials and devices

• US 9,518,063 B2
• Filed: 06/10/2015
• Issued: 12/13/2016
• Est. Priority Date: 01/16/2009
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Lin, Chun, Ma, Bin, Kwong, Raymond, Dyatkin, Alexey Borisovich, Wu, Yonggang, Elshenawy, Zeinab M.
• Primary Examiner(s): Otton, Alicia L
• Application Number:
  US14/735,589
• Publication Number:
  US 20150274749A1
• Time in Patent Office: 552 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07D 491/04 Ortho-condensed systems
• CPC Class Codes: C07D 491/048 the oxygen-containing ring being five-membered
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: 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
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/20 characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/155 comprising dopants
• CPC Class Codes: H10K 50/156 comprising a multilayered structure
• CPC Class Codes: H10K 50/157 between the light-emitting layer and the cathode
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 59/00 Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
• CPC Class Codes: H10K 59/32 Stacked devices having two or more layers, each emitting at different wavelengths
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/622 : containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 : containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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

1. A process comprising:

treating an acetic acid solution of an intermediate having the formula

2. The process of claim 1, wherein Y is S.

3. The process of claim 1, wherein Y is O.

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

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

6. The process of claim 1, wherein R₁ is halide.

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

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

9. 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.

10. The process of claim 1, wherein Y is S and the yield of