MATERIALS WITH AZA-DIBENZOTHIOPHENE OR AZA-DIBENZOFURAN CORE FOR PHOLED

• US 20100187984A1
• Filed: 12/28/2009
• Published: 07/29/2010
• Est. Priority Date: 01/16/2009
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Yonggang, Wu, Ma, Bin, Kwong, Raymond, Lin, Chun, Dyatkin, Alexey Borisovich, Elshenawy, Zeinab M.
• Granted Patent: US 9,067,947 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• 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 for making an aza-dibenzothiophene compound or an aza-dibenzofuran compound, comprising:

treating an acetic acid solution of an amino-arylthio pyridine 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.

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 and the amino-arylthio pyridine intermediate is treated with H₂SO₄ prior to treatment with ^tBuONO.

10. The process of claim 1, wherein the yield of

is greater than 50%.

11. A compound having the formula:

wherein X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ are independently selected from the group consisting of a carbon atom and a nitrogen atom;

wherein at least one of X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ is a nitrogen atom;

wherein Y is S or O;

wherein R₁ and R₂ may represent mono, di, tri, or tetra substitutions;

wherein R₁ and R₂ are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and

wherein at least one of R₁ and R₂ is selected from the group consisting of;

wherein R′

₁, R^′

₂, R′

₃, and R′

₄ may represent mono, di, tri, tetra or penta substitutions; and

wherein R′

₁, R′

₂, R′

₃, and R′

₄ are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.

12. The compound of claim 11, wherein the compound has the formula:

wherein X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ are independently selected from the group consisting of a carbon atom and a nitrogen atom;

wherein at least one of X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ is a nitrogen atom;

wherein Y is S or O;

wherein R₁ and R₂ may represent mono, di, tri, or tetra substitutions;

wherein R₁ and R₂ are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and

wherein at least one of R₁ and R₂ is selected from the group consisting of;

wherein R′

₁, R′

₂, R′

₃, and R′

₄ may represent mono, di, tri, tetra or penta substitutions; and

wherein R′

₁, R′

₂, R′

₃, and R′

₄ are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.

13. The compound of claim 12, wherein m and n are 0, 1, 2, 3, or 4;

and wherein m+n is equal to or greater than 2 and m+n is equal to or less than 6.

14. The compound of claim 11, wherein the compound is selected from the group consisting of:

15. The compound of claim 11, wherein the compound is selected from the group consisting of:

16. A first device comprising an organic light emitting device, further comprising:

an anode;

a cathode;

an organic layer disposed between the anode and the cathode, the organic layer further comprising a compound having the formula;

wherein X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ are independently selected from the group consisting of a carbon atom and a nitrogen atom;

wherein at least one of X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ is a nitrogen atom;

wherein Y is S or O;

wherein R₁ and R₂ may represent mono, di, tri, or tetra substitutions;

wherein R₁ and R₂ are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and

wherein at least one of R₁ and R₂ is selected from the group consisting of;

wherein R′

₁, R′

₂, R′

₃, and R′

₄ may represent mono, di, tri, tetra or penta substitutions; and

wherein R′

₁, R′

₂, R′

₃, and R′

₄ are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.

18. The device of claim 16, comprising:

an anode;

a cathode;

an organic layer disposed between the anode and the cathode, the organic layer further comprising a compound having the formula;

wherein X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ are independently selected from the group consisting of a carbon atom and a nitrogen atom;

wherein at least one of X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ is a nitrogen atom;

wherein Y is S or O;

wherein R₁ and R₂ may represent mono, di, tri, or tetra substitutions;

wherein R₁ and R₂ are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and

wherein at least one of R₁ and R₂ is selected from the group consisting of;

wherein R′

₁, R′

₂, R′

₃, and R′

₄ may represent mono, di, tri, tetra or penta substitutions; and

wherein R′

₁, R′

₂, R′

₃, and R′

₄ are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.

19. The device of claim 16, wherein the organic layer is an emissive layer and the compound having the formula

is a host.

20. The device of claim 16, wherein the organic layer further comprises an emissive dopant and the emissive dopant has the formula:

wherein R₁ and R₂ are each independently selected from the group consisting of hydrogen, alkyl, and aryl.

17. The device of claim 17, wherein the first device is a consume product.