Fluorescent, semi-conductive polymers, and devices comprising them

• US 7,700,366 B2
• Filed: 12/06/2004
• Issued: 04/20/2010
• Est. Priority Date: 12/04/2003
• Status: Expired due to Fees

• Current Assignee: Massachusetts Institute of Technology
• Original Assignee: Massachusetts Institute of Technology
• Inventors: Kim, Youngmi, Swager, Timothy M.
• Primary Examiner(s): Griffin; Walter D
• Assistant Examiner(s): Ramdhanie; Bobby
• Application Number:
  US11/005,634
• Publication Number:
  US 20050196775A1
• Time in Patent Office: 1,961 Days
• Field of Search: 436/72
• US Class Current: 436/172
• 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 61/06 prepared by ring-opening of carbocyclic compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1425 Non-condensed systems
• CPC Class Codes: G01N 33/582 with fluorescent label
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/114 Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

The present invention relates to fluorescent, semiconductive polymers comprising electron withdrawing groups bonded to the polymer. The invention also relates to a method of detecting analytes comprising contacting the analyte with the fluorescent, semiconductive polymers of the present invention. The invention also relates to light emitting devices, photovoltaic devices, and sensors comprising the fluorescent, semiconductive polymers of the present invention.

Claims

1. A fluorescent, semiconductive polymer comprising a conjugated backbone and electron withdrawing groups bonded to the polymer, wherein the fluorescent, semiconductive polymer is represented by formula Ia, Ib, Ic or Id:

2. The fluorescent, semiconductive polymer of claim 1, wherein R is an ester or a perhalogenated alkyl group.

3. The fluorescent, semiconductive polymer of claim 1, wherein R is an ester.

4. The fluorescent, semiconductive polymer of claim 1, wherein R is —

CO₂CH₃ or —

CO₂C(CH₃)₃.

5. The fluorescent, semiconductive polymer of claim 1, wherein R is a perfluorinated alkyl group.

6. The fluorescent, semiconductive polymer of claim 1, wherein R is a perfluorinated C_1-12 alkyl group.

7. The fluorescent, semiconductive polymer of claim 1, wherein R₁ is —

CF₃, —

C₄F₉, C₈F₁₇, or —

C₁₀F₂₁.

8. The fluorescent, semiconductive polymer of claim 1, wherein R₁ is —

CF₃.

9. The fluorescent, semiconductive polymer of claim 1, wherein R₁ is —

C₄F₉.

10. The fluorescent, semiconductive polymer of claim 1, wherein R₁ is —

C₈F₁₇.

11. The fluorescent, semiconductive polymer of claim 1, wherein R₁ is —

C₁₀F₂₁.

12. The fluorescent, semiconductive polymer of claim 1, wherein R₁ is H.

13. The fluorescent, semiconductive polymer of claim 1, wherein A is a fused benzene ring.

14. The fluorescent, semiconductive polymer of claim 1, wherein n is greater than about 10, 100, or 1000.

15. The fluorescent, semiconductive polymer of claim 1, wherein R is —

CO₂Me, R₁ is H, A is a fused benzene ring, and n is greater than about 10, 100, or 1000.

16. The fluorescent, semiconductive polymer of claim 1, wherein R is —

CF₃, R₁ is H, A is a fused benzene ring, and n is greater than about 10, 100, or 1000.

17. A fluorescent, semiconductive polymer comprising a conjugated backbone and electron withdrawing groups bonded to the polymer, wherein the fluorescent, semiconductive polymer comprises formula II:

18. The fluorescent, semiconductive polymer of claim 17, wherein B is a double bond.

19. The fluorescent, semiconductive polymer of claim 17, wherein B is a triple bond.

20. The fluorescent, semiconductive polymer of claim 17, wherein B is aryl.

21. The fluorescent, semiconductive polymer of claim 17, wherein R is a perhalogenated alkyl.

22. The fluorescent, semiconductive polymer of claim 17, wherein R is a perfluorinated alkyl.

23. The fluorescent, semiconductive polymer of claim 17, wherein R is an ester.

24. The fluorescent, semiconductive polymer of claim 17, wherein R is —

CO₂CH₃ or —

CO₂C(CH₃)₃.

25. The fluorescent, semiconductive polymer of claim 17, wherein R is —

CF₃, —

C₄F₉, —

C₈F₁₇, or —

C₁₀F₂₁.

26. The fluorescent, semiconductive polymer of claim 17, wherein R is —

CF₃.

27. The fluorescent, semiconductive polymer of claim 17, wherein R is —

C₄F₉.

28. The fluorescent, semiconductive polymer of claim 17, wherein R is —

C₈F₁₇.

29. The fluorescent, semiconductive polymer of claim 17, wherein R is —

C₁₀F₂₁.

30. The fluorescent, semiconductive polymer of claim 17, wherein at least one R¹ is a perfluorinated C_1-12 alkyl.

31. The fluorescent, semiconductive polymer of claim 17, wherein two R¹ are perfluorinated C_1-12 alkyls.

32. The fluorescent, semiconductive polymer of claim 17, wherein at least one R¹ is a C_1-12 alkoxy group.

33. The fluorescent, semiconductive polymer of claim 17, wherein two R¹ are C_1-12 alkoxy groups.

34. The fluorescent, semiconductive polymer of claim 17, wherein a is 2.

35. The fluorescent, semiconductive polymer of claim 17, wherein m and n are greater than about 10, 100, or 1000.

36. The fluorescent, semiconductive polymer of claim 17, wherein two sets of adjacent R¹ each form a monocyclic ring.

37. The fluorescent, semiconductive polymer of claim 17, wherein two sets of adjacent R¹ each form a bicyclic ring.

38. The fluorescent, semiconductive polymer of claim 17, wherein two sets of adjacent R¹ each form a tricyclic ring.

39. The fluorescent, semiconductive polymer of claim 17, wherein two sets of adjacent R¹ each form a tetracyclic ring.

40. The fluorescent, semiconductive polymer of claim 17, wherein two sets of adjacent R¹ each form either a monocyclic, bicyclic, tricyclic, or tetracyclic structure.

41. The fluorescent, semiconductive polymer of claim 17, wherein two sets of R¹ are each independently selected from the group consisting of