Solution processable doped triarylamine hole injection materials

• US 8,963,132 B2
• Filed: 03/25/2010
• Issued: 02/24/2015
• Est. Priority Date: 03/25/2010
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Cheon, Kwang Ohk
• Primary Examiner(s): Ho, Anthony
• Application Number:
  US13/583,539
• Publication Number:
  US 20130112951A1
• Time in Patent Office: 1,797 Days
• Field of Search: 257/40, 257/E51.001
• US Class Current: 257/40
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/155 comprising dopants
• CPC Class Codes: H10K 50/17 Carrier 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 71/30 Doping active layers, e.g. electron transporting layers
• CPC Class Codes: H10K 71/40 Thermal treatment, e.g. annealing in the presence of a solvent vapour
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/649 Aromatic compounds comprising a hetero atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

Methods for fabricating a solution-processed OLED are provided. The methods include depositing an organic layer comprising mixture of an organic electron acceptor and an organic electron donor to form a layer that is insoluble to a non-polar solvent. Devices containing the organic layer may demonstrate improved lifetime and have a lower operating voltage while maintaining good luminous efficiency.

Claims

1. A method of fabricating an organic light emitting device, the method comprising:

providing an electrode;

depositing a first organic layer in contact with the electrode by a solution process, wherein the first organic layer comprises an organic electron acceptor; and

an organic electron donor having the formula;

2. The method of claim 1, wherein the non-polar solvent is selected from the group consisting of benzene, carbon tetrachloride, cyclohexane, 1,2-dichloroethane, dichloromethane, di-ethyl ether, heptane, hexane, methyl-t-butyl ether, pentane, di-iso-propyl ether, toluene, and xylene.

3. The method of claim 1, wherein the non-polar solvent is toluene.

4. The method of claim 1, wherein the organic electron donor has the formula:

5. The method of claim 1, wherein the organic electron donor has the formula:

6. The method of claim 1, wherein the organic electron donor has the formula:

7. The method of claim 1, wherein the electrode is an anode, and the first organic layer is deposited in contact with the anode.

8. The method of claim 1, wherein a second organic layer containing a non-polar solvent is deposited over the first organic layer, and the first organic layer is insoluble to the non-polar solvent in the second organic layer.

9. The method of claim 1, wherein the first organic layer is a hole injection layer.

10. The method of claim 1, wherein the second organic layer is a hole transporting layer, a hole blocking layer, an electron transporting layer, an electron injection layer, or an emissive layer.

11. The method of claim 1, wherein the organic electron acceptor is selected from the group of compounds having the formulas:

12. The method of claim 1, wherein the organic electron acceptor is:

13. The method of claim 1, wherein the organic electron donor is selected from the group consisting of:

14. The method of claim 1, wherein the organic electron acceptor is:

15. The method of claim 14, wherein the organic electron donor is:

16. The method of claim 1, wherein the solution process is spin coating or inkjet printing.

17. The method of claim 1, wherein the organic electron acceptor and the organic electron donor are mixed at a mole ratio of 1:

1 or 2;

1.

18. The device of claim 1, wherein the insoluble organic layer forms when the composition is heated at a temperature no less than about 100°

C. and no more than about 250°

C.

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

an anode;

a cathode; and

a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises an organic electron acceptor; and

an organic electron donor having the formula;

20. The device of claim 19, wherein the organic electron acceptor and the organic electron donor form a layer that is insoluble in a non-polar solvent.