OLEDs containing thermally stable glassy organic hole transporting materials

• US 6,150,043 A
• Filed: 04/10/1998
• Issued: 11/21/2000
• Est. Priority Date: 04/10/1998
• Status: Expired due to Term

• Current Assignee: Princeton University, University of Southern California
• Original Assignee: The Trustees of Princeton University (Princeton University), University of Southern California
• Inventors: O'Brien, Diarmuid, Forrest, Stephen R., Thompson, Mark E., Koene, Bryan E., Douglas, Loy
• Primary Examiner(s): Higel, Floyd D.
• Assistant Examiner(s): SACKEY, EBENEZER O
• Application Number:
  US09/058,305
• Time in Patent Office: 956 Days
• Field of Search: 252/307.17, 428/917, 428/690, 540/543, 313/504, 313/506
• US Class Current: 428/690
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: C09K 2211/186 of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg
• CPC Class Codes: H05B 33/28 of translucent electrodes
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2102/3031 Two-side emission, e.g. transparent OLEDs [TOLED]
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/321 Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

The present invention is directed to organic light emitting devices comprising a heterostructure for producing electroluminescence having a hole transporting layer with a glass structure. The hole transporting layer comprises a compound having a symmetric molecular structure. The end groups of the symmetric molecule are hole transporting amine moieties having an unsaturated linkage between two arenes.

Claims

1. An organic light emitting device comprising a heterostructure for producing electroluminescence, wherein the heterostructure comprises a hole transporting layer having a glass structure, and wherein the hole transporting layer comprises a compound having the formula:

##STR15## wherein A consists of one or two phenyl groups and R₁ and R₂ are, independently of one another, selected from the group consisting of hydrogen, an alkyl group, a phenyl group, a substituted alkyl group and a substituted phenyl group, and wherein R₁ and R₂ may be bridged.

2. The organic light emitting device of claim 1, wherein the compound has the formula:

##STR16##

3. The organic light emitting device of claim 1, wherein the compound has the formula:

4. The organic light emitting device of claim 1, wherein the compound has the formula:

5. The organic light emitting device of claim 1, wherein R₁ and R₂ are the same.

6. The organic light emitting device of claim 1, wherein R₁ and R₂ are different.

7. The organic light emitting device of claim 1, wherein the compound has the formula:

8. The organic light emitting device of claim 1, wherein the compound is the predominant component in the hole transporting layer.

9. The organic light emitting device of claim 1, wherein the compound is present as a dopant in the hole transporting layer.

10. The organic light emitting device of claim 1 wherein the heterostructure for producing electroluminescense comprises, in sequence, a substrate, a cathode layer, an electron transporting layer, the hole transporting layer and an anode layer.

11. The organic light emitting device of claim 1 wherein the heterostructure for producing electroluminescense comprises, in sequence, a substrate, a cathode layer, an electron transporting layer, the hole transporting layer, a hole injector layer and an anode layer.

12. The organic light emitting device of claim 1 wherein the heterostructure for producing electroluminescense comprises, in sequence, a substrate, a cathode layer, an electron transporting layer, an emissive layer, the hole transporting layer and an anode layer.

13. The organic light emitting device of claim 1 wherein the heterostructure for producing electroluminescense comprises, in sequence, a substrate, a cathode layer, an electron transporting layer, the hole transporting layer, an emissive layer, a hole injector layer and an anode layer.

14. The organic light emitting device of claim 1 wherein the heterostructure for producing electroluminescense comprises, in sequence, a substrate, an anode layer, the hole transporting layer, an electron transporting layer, and a cathode layer.

15. The device of claim 1, wherein the device is incorporated into a display.

16. The device of claim 1, wherein the device is incorporated into a vehicle.

17. The device of claim 1, wherein the device is incorporated into a computer.

18. The device of claim 1, wherein the device is incorporated into a television.

19. The device of claim 1, wherein the device is incorporated into a printer.

20. The device of claim 1, wherein the device is incorporated into a wall, theater or stadium screen.

21. The device of claim 1, wherein the device is incorporated into a billboard or a sign.

22. The organic light emitting device of claim 1 wherein said compound has the formula: