Soluble conjugated polymers

• US 8,309,672 B2
• Filed: 09/06/2005
• Issued: 11/13/2012
• Est. Priority Date: 09/03/2004
• Status: Expired due to Fees

• Current Assignee: Regents of the University of California (University of California)
• Original Assignee: Regents of the University of California (University of California)
• Inventors: Bazan, Guillermo C., Liu, Bin, Gong, Xiong, Heeger, Alan J., Ma, Wanli, Iyer, Parameswar K.
• Primary Examiner(s): MULLIS, JEFFREY C
• Application Number:
  US11/221,123
• Publication Number:
  US 20060079647A1
• Time in Patent Office: 2,625 Days
• Field of Search: 525/540, 525/7, 525/8, 525/397, 525/403, 525/405
• US Class Current: 528/7
• CPC Class Codes: C08F 257/00 Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
• CPC Class Codes: C08F 279/02 on to polymers of conjugated dienes
• CPC Class Codes: C08F 287/00 Macromolecular compounds obtained by polymerising monomers on to block polymers
• CPC Class Codes: C08F 289/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
• CPC Class Codes: C08F 291/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• CPC Class Codes: C08F 8/44 Preparation of metal salts or ammonium salts
• CPC Class Codes: C08G 61/02 Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
• CPC Class Codes: C08G 61/123 derived from five-membered heterocyclic compounds
• CPC Class Codes: C08G 61/124 with a five-membered ring containing one nitrogen atom in the ring
• CPC Class Codes: C08G 61/125 with a five-membered ring containing one oxygen atom in the ring
• CPC Class Codes: C08G 61/126 with a five-membered ring containing one sulfur atom in the ring
• CPC Class Codes: C08G 73/00 Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00 polycarbodiimides prepared from isocyanates C08G18/025, C08G18/797
• CPC Class Codes: C08G 73/06 Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
• CPC Class Codes: C08G 73/08 Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 51/006 grafted on to block copolymers containing at least one sequence of polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08L 51/04 grafted on to rubbers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/10 Organic polymers or oligomers
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/113 : Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/1135 : Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/114 : Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: H10K 85/115 : Polyfluorene; Derivatives thereof
• CPC Class Codes: H10K 85/151 : Copolymers

Abstract

Methods, compositions and articles of manufacture involving soluble conjugated polymers are provided. The conjugated polymers have a sufficient density of polar substituents to render them soluble in a polar medium, for example water and/or methanol. The conjugated polymer may desirably comprise monomers which alter its conductivity properties. In some embodiments, the inventors have provided cationic conjugated polymers (CCPs) comprising both solubilizing groups and conductive groups, resulting in conductive conjugated polymers soluble in polar media. The different solubility properties of these polymers allow their deposition in solution in multilayer formats with other conjugated polymers. Also provided are articles of manufacture comprising multiple layers of conjugated polymers having differing solubility characteristics. Embodiments of the invention are described further herein.

Claims

1. A conjugated polymer comprising:

a polymer backbone consisting essentially of a repeat unit of the formula (I)

2. The conjugated polymer of claim 1, wherein R₁ and R₂ are not present;

A, B, C and D are H; and

R₃ and R₄ are (N,N,N-trimethylammonium)hexyl.

3. The conjugated polymer of claim 1, wherein E, F, R′

₁ and R′

₂ are not present;

A₁ and B₁ are H; and

X is —

O—

.

4. The conjugated polymer of claim 1, wherein the polymer is poly {[9,9-bis(6′

-(N,N,N-trimethylammonium)hexyl)-fluorene-2,7-diyl]-alt-[2,5-bis(p-phenylene)-1,3,4-oxadiazole]}(“

PFON⁺(CH₃)₃I⁻

-PBD”

).

5. The conjugated polymer of claim 1, wherein the polymer is soluble in a predominantly aqueous medium.

6. The conjugated polymer of claim 1, wherein the polymer is soluble in water.

7. The conjugated polymer of claim 1, wherein the polymer is soluble in methanol.

8. The conjugated polymer of claim 1, wherein the polymer is purified.

9. The conjugated polymer of claim 1, wherein the polymer is synthesized through a Suzuki coupling reaction.

10. The conjugated polymer of claim 1, wherein the polymer is a copolymer.

11. The conjugated polymer of claim 1, wherein the polymer is purified.

12. A film comprising the conjugated polymer of claim 1.

13. The film of claim 12, wherein the film has a thickness of less than 200 nm.

14. A substrate comprising a layer of the conjugated polymer of claim 1.

15. A solution comprising the conjugated polymer of claim 1 and a solvent.

16. The solution of claim 15, wherein the solution further comprises a surfactant.

17. The solution of claim 15, wherein the solution comprises water.

18. The solution of claim 15, wherein the solution consists essentially of water as the solvent.

19. The solution of claim 15, wherein the solution comprises an alcohol.

20. The solution of claim 15, wherein the solution consists essentially of an alcohol as the solvent.

21. The solution of claim 15, wherein the solution comprises methanol.

22. The solution of claim 15, wherein the solution consists essentially of methanol as the solvent.

23. An inkjet cartridge comprising the solution of claim 15.

24. The conjugated polymer of claim 1, wherein X is —

O—

.