Organic light-emitting devices

• US 9,647,221 B2
• Filed: 04/24/2015
• Issued: 05/09/2017
• Est. Priority Date: 07/14/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Xia, Chuanjun, Harikrishna Mohan, Siddharth, Cheon, Kwang-Ohk, Brooks, Jason
• Primary Examiner(s): VETERE, ROBERT A
• Application Number:
  US14/695,833
• Publication Number:
  US 20150255738A1
• Time in Patent Office: 746 Days
• Field of Search: None
• CPC Class Codes: C07F 11/005 compounds without a metal-carbon linkage
• CPC Class Codes: C07F 7/025 without C-silicon linkages
• CPC Class Codes: C07F 7/28 Titanium compounds
• CPC Class Codes: C07F 9/005 Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2102/00 Constructional details relating to the organic devices covered by this subclass
• CPC Class Codes: H10K 2102/351 Thickness
• 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 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 71/00 Manufacture or treatment specially adapted for the organic devices covered by this subclass
• CPC Class Codes: H10K 71/12 using liquid deposition, e.g. spin coating
• CPC Class Codes: H10K 85/00 Organic materials used in the body or electrodes of devices covered by this subclass
• CPC Class Codes: H10K 85/341 Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/611 Charge transfer complexes
• 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 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: Y10T 428/31678 : Of metal

Abstract

Organic electronic devices comprising a covalently bonded organic/inorganic composite layer. The composite layer may be formed by the reaction of a metal alkoxide with a charge transport compound having one or more hydroxyl groups. Examples of metal alkoxides that can be used include vanadium alkoxides, molybdenum alkoxides, titanium alkoxides, or silicon alkoxides. This composite layer can be used for any of the various charge conducting layers in an organic electronic device, including the hole injection layer.

Claims

1. An organic electronic device comprising:

a first electrode;

a second electrode; and

a covalently bonded composite organic/inorganic layer between the first and second electrodes, wherein the covalently bonded composite organic/inorganic layer comprising a metal-organic material comprising a metal alkoxide bonded to a triarylamine moiety having a hydroxyl group by stable coordination bonds, wherein in the metal-organic material, all stable coordination bonds with the metal atom of the metal alkoxide compound are covalent metal-oxygen-carbon bonds.

2. The device of claim 1, wherein the charge transport compound is a hole transport compound and the composite layer is a hole injection layer.

3. The device of claim 2, wherein the metal alkoxide is a vanadium alkoxide, a molybdenum alkoxide, or a titanium alkoxide.

4. The device of claim 1, wherein the charge transport compound is an electron transport compound and the composite layer is an electron injection layer.

5. The device of claim 1, wherein the composite layer is a hole injection layer directly adjacent the first electrode.

6. The device of claim 5, wherein the hole injection layer has a thickness of 50-750 Å

.

7. The device of claim 1, wherein the device is an organic light-emitting device.

8. The device of claim 7, further comprising an emissive layer between the composite layer and the second electrode.

9. The device of claim 8, wherein the composite layer is a hole injection layer directly adjacent the first electrode.

10. The device of claim 8, wherein the emissive layer comprises a phosphorescent emitting dopant.

11. The device of claim 8, wherein the emissive layer comprises a fluorescent emitting compound.

12. The device of claim 8, further comprising a hole blocking layer between the emissive layer and the second electrode.

13. The device of claim 1, wherein the metal alkoxide is a vanadium alkoxide or a molybdenum alkoxide.

14. A covalently bonded composite organic/inorganic layer comprising a metal-organic material comprising a metal alkoxide bonded to a triarylamine moiety having a hydroxyl group by stable coordination bonds, wherein in the metal-organic material, all stable coordination bonds with the metal atom of the metal alkoxide compound are covalent metal-oxygen-carbon bonds.

15. The covalently bonded composite organic/inorganic layer of claim 14, wherein the metal alkoxide is a vanadium alkoxide or a molybdenum alkoxide.

16. The composite layer of claim 14, wherein the charge transport compound includes a triarylamine moiety.