Modified electrodes using functional organic materials and electronic devices therefrom

• US 20060234059A1
• Filed: 04/15/2005
• Published: 10/19/2006
• Est. Priority Date: 04/15/2005
• Status: Active Grant

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Liu, Jie, Cella, James Anthony, Anton Heller, Christian Maria
• Granted Patent: US 8,741,442 B2
• Time in Patent Office: Days
• US Class Current: 428/411.100
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 85/141 comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
• 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: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31507 Of polycarbonate
• CPC Class Codes: Y10T 428/31678 Of metal
• CPC Class Codes: Y10T 428/31692 Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31721 Of polyimide
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers

Abstract

A surface modified electrode, included in an electronic device comprises an electrode layer, and a functional organic material. The functional organic material comprises an amine-substituted polymeric material which is on the surface of and in contact with the electrode layer. Such surface modified electrodes are useful for producing electronic devices.

Claims

1. A surface modified electrode comprising:

an electrode layer; and

a functional organic material disposed on the electrode layer;

wherein the functional organic material comprises an amine-substituted polymeric material, and is on the surface of and in contact with the electrode layer and wherein the surface modified electrode is included in an electronic device.

2. The surface modified electrode of claim 1, wherein the electrode layer comprises at least one metal or alloys thereof.

3. The surface modified electrode of claim 1, wherein the electrode layer comprises indium tin oxide.

4. The surface modified electrode of claim 1, wherein the amine-substituted polymeric material comprises a poly(alpha-olefin), poly(alkenylaromatic), polyphenylene, polyfluorene, polycarbonates, polyimides, polyesters, copolymers thereof, or blends thereof.

5. The surface modified electrode of claim 1, wherein the amine-substituted polymeric material comprises one or more crosslinkable group comprising a vinyl group, an allyl group, a styryl group, an organosilicon group, or an alkynyl group, or any combination thereof.

6. The surface modified electrode of claim 1, wherein the amine-substituted polymeric material comprises a repeat unit having a structure (II):

wherein [A] comprises a carbocyclic, [B] comprises a single bond or a spacer group, R¹ and R² comprise independently of each other hydrogen atom, C₁-C₃₀ aliphatic radicals, C₃-C₃₀ cycloaliphatic groups, C₃-C₃₀ aromatic radicals, or any combination thereof, and “

p”

comprises an integer from 1 to the maximum number of positions available for substitution on [A].

7. The surface modified electrode of claim 6, wherein [A] comprises substituted phenylene, unsubstituted phenylene, naphthylene, anthracenylene, fluorenylene, or any combination thereof.

8. The surface modified electrode of claim 6, wherein the amine-substituted polymeric material comprises dialkylamino groups, monoalkylamino groups, NH₂ groups, or any combination thereof.

9. The surface modified electrode of claim 8, wherein [A] comprises a phenylene, a naphthylene, an anthracenylene, or any combinations thereof.

10. The surface modified electrode of claim 9, wherein [B] comprises a methylene group.

11. The surface modified electrode of claim 1, wherein the amine-substituted polymeric material comrises a member having a structure (IV):

wherein [B] comprises a single bond or a spacer group, or combination thereof, and R¹ and R² comprise independently of each other hydrogen atoms, C₁-C₃₀ aliphatic radicals, C₃-C₃₀ cycloaliphatic radicals, C₃-C₃₀ aromatic radicals, or any combination thereof.

12. The surface modified electrode of claim 11, wherein the electrode layer comprises indium tin oxide.

13. The surface modified electrode of claim 11, wherein the amine-substituted polymeric material comprises at least one of poly[(N,N-dibutylaminomethyl)styrene], poly[(N,N-dimethylaminomethyl)styrene], poly[(N,N-dipropylaminomethyl)styrene], poly[(N,N-ethylmethylaminomethyl)styrene], or poly[(N,N-diethylaminomethyl)styrene].

14. An electronic device comprising:

a first conductive layer;

a second conductive layer; and

an electro-active material layer disposed between the first and second conductive layers;

wherein at least one of the first and second conductive layers is modified by a functional organic material, the functional organic material comprising an amine-substituted polymeric material.

15. The electronic device of claim 14, wherein the electro-active material layer comprises the amine-substituted polymeric material.

16. The electronic device of claim 14, wherein at least one of the first and second conductive layers is substantially transparent.

17. The electronic device of claim 14, comprising at least one of a charge transporting material, a charge injection material, or a hole transport material.

18. The electronic device of claim 14, wherein the electronic device is selected from the group consisting of an organic photovoltaic device, a photodetector, a display device, an organic light emitting device, a sensor, an electrochromic device, and a field effect transistor.

19. The electronic device of claim 14, wherein the electro-active material layer comprises at least one of a fluorescent dye or a phosphorescent dye.

20. The electronic device of claim 14, wherein the amine-substituted polymeric material further includes at least one matrix polymeric material.

21. A method for fabricating an electronic device, the method comprising:

disposing a layer of a functional organic material material on the surface of the and in contact with a first conductive layer to form a surface modified electrode; and

disposing an electro-active material layer between the surface modified electrode and a second conductive layer;

wherein the functional organic material comprises an amine-substituted polymeric material.

22. The method of claim 21, wherein said disposing comprises spin casting, drop casting, ink-jet printing, or gravure coating techniques, physical vapor deposition, or any combination thereof.

23. A device comprising:

a display unit, the display unit comprising a plurality of electronic devices, wherein at least one of the electronic devices comprises;

a first conductive layer;

a second conductive layer; and

an electro-active material layer disposed between the first and second conductive layers,

wherein at least one of the first and second conductive layers is modified by a functional organic material, the functional organic material comprising an amine-substituted polymeric material; and

further wherein the functional organic material is on the surface of and in contact with at least one of the first and second conductive layers.

24. A method of operating an electronic device, the method comprising:

applying an electrical field or light energy to the electronic device to convert between electrical energy and light energy, wherein the electronic device comprises;

a first conductive layer;

a second conductive layer; and

an electro-active material layer disposed between the first and second conductive layers,

wherein at least one of the first and second conductive layers is modified by a functional organic material, the functional organic material comprising an amine-substituted polymeric material; and

further wherein the functional organic material is on the surface of and in contact with at least one of the first and second conductive layers.