Conductive copolymer, conductive copolymer composition, film and opto-electronic device using the same

• US 7,875,208 B2
• Filed: 11/08/2007
• Issued: 01/25/2011
• Est. Priority Date: 11/08/2006
• Status: Active Grant

• Current Assignee: Cheil Industries Incorporated
• Original Assignee: Cheil Industries Incorporated
• Inventors: Huh, Dal Ho, Lee, Jeong Woo, Chae, Mi Young, Lee, Tae Woo
• Primary Examiner(s): Kopec; Mark
• Assistant Examiner(s): Thomas; Jaison P
• Application Number:
  US11/936,843
• Publication Number:
  US 20080105854A1
• Time in Patent Office: 1,174 Days
• Field of Search: 252/500, 526/251, 528/373, 528/422, 528/423
• US Class Current: 252/500
• CPC Class Codes: H01B 1/125 comprising aliphatic main chains, e.g. polyactylenes
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof

Abstract

Disclosed herein is a conductive copolymer. The conductive copolymer can prevent water-absorbance, lower the concentration of polyacid contained in a molecule and exhibit superior film characteristics and excellent storage stability via a reduction in aggregation between molecules, as well as impart improved efficiency and lifetime to optoelectronic devices. The conductive copolymer includes a conductive polymer doped with a polyacid copolymer represented by Formula 1 below:

Further disclosed are a conductive copolymer composition, a conductive copolymer composition film and an organic optoelectronic device, each including the conductive copolymer.

Claims

1. A conductive copolymer comprising a conductive polymer doped with a polyacid copolymer represented by Formula 1 below:

2. The conductive copolymer according to claim 1, wherein said cation is selected from the group consisting of metal ions and organic ions.

3. The conductive copolymer according to claim 2, wherein said metal ions are selected from the group consisting of Na⁺, K⁺, Li⁺, Mg²⁺, Zn²⁺and Al³⁺;

and said organic ions, are selected from the group consisting of H⁺, NH₃⁺and CH₃(—

CH₂—

)_n, wherein n is an integer from 1 to 50.

4. The conductive copolymer according to claim 1, wherein said anion is selected from the group consisting of PO₃⁻

, SO₃⁻

, COO⁻

, I⁻

and CH₃COO⁻

.

5. The conductive copolymer according to claim 1, wherein said cation is H⁺ and said anion is SO₃⁻

.

6. The conductive copolymer according to claim 1, wherein A is a substituted or unsubstituted C₆-C₃₀ aryl group.

7. The conductive copolymer according to claim 6, wherein A is phenyl.

8. The conductive copolymer according to claim 1, wherein said polyacid copolymer of Formula 1 comprises a compound of Formula (19) below

9. The conductive copolymer according to claim 8, wherein the conductive polymer comprises at least two monomers selected from pyrrole or thiophene represented by the following Formula 4, and derivatives thereof;

10. The conductive copolymer according to claim 1, wherein the conductive polymer comprises at least two monomers selected from the group consisting of polyphenylene, polyphenylenevinylene, polyaniline represented by the following Formula 3 and derivatives thereof;

pyrrole or thiophene represented by the following Formula 4, and derivatives thereof; and

cyclic compounds represented by the following Formula 5 and derivatives thereof;

11. The conductive copolymer according to claim 1, wherein said conductive polymer comprises 3,4-ethylenedioxythiophene (EDOT).

12. A conductive copolymer composition comprising:

a conductive copolymer comprising a conductive polymer doped with a polyacid copolymer according to claim 1; and

a physical or chemical crosslinking agent.

13. The conductive copolymer composition according to claim 12, wherein the conductive polymer comprises at least two monomers selected from the group consisting of polyphenylene, polyphenylenevinylene, polyaniline represented by the following Formula 3 and derivatives thereof;

pyrrole or thiophene represented by the following Formula 4 and derivatives thereof; and

cyclic compounds represented by the following Formula 5 and derivatives thereof;

14. The conductive copolymer composition according to claim 12, comprising said physical crosslinking agent in an amount of about 0.001 to about 5 parts by weight, based on 100 parts by weight of the conductive copolymer composition.

15. The conductive copolymer composition according to claim 12, comprising said chemical crosslinking agent in an amount of about 0.001 to about 50 parts by weight, based on 100 parts by weight of the conductive copolymer composition.

16. The conductive copolymer composition according to claim 12, wherein the physical crosslinking agent is selected from the group consisting of glycerol, butanol, polyvinyl alcohol, polyethyleneglycol, polyethylenimine and polyvinylpyrolidone.

17. The conductive copolymer composition according to claim 12, wherein the chemical crosslinking agent is selected from the group consisting of tetraethyloxysilane (TEOS), polyaziridine, melamine polymers and epoxy polymers.

18. The conductive copolymer composition according to claim 12, further comprising a solvent.

19. The conductive copolymer composition according to claim 18, wherein said solvent comprises at least one solvent selected from the group consisting of water, alcohol, dimethylformamide (DMF), dimethylsulfoxide (DMSO), toluene, xylene and chlorobenzene.

20. A conductive copolymer composition film for an organic opto-electronic device prepared from a conductive copolymer composition according to claim 12.

21. An organic opto-electronic device comprising a conductive copolymer composition film according to claim 20.

22. The conductive copolymer according to claim 1, wherein:

A is substituted or unsubstituted C₆-C₃₀ aryl group; and

B is SO₃H.