IP Library Granted Patent US 9,376,623
Granted Patent B2
US 9,376,623 · App. 12/312,259 · Granted Jun 28, 2016

Compositions including polymers aligned via interchain interactions

Inventors: Timothy M. Swager (Newton, MA); Johan T. V. Hoogboom (Deventer, NL)
Assignee: Massachusetts Institute of Technology
C09K19/542C08G81/00C08L65/00C08L101/12C08G2261/148C08G2261/3422G02F2001/13345
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Quick Facts
Patent No.
US 9,376,623
App. No.
12/312,259
Granted
Jun 28, 2016
Kind
B2
Abstract

The present invention provides compositions, devices and methods related to the alignment of materials including polymers. In some cases, the present invention comprises the assembly of molecules (e.g., polymers) via intermolecular interactions to produce extended networks, which may have enhanced properties relative to the individual molecules. Such networks may be advantageous for use in electronics, photovoltaics, sensor applications, and the like. In some embodiments, the present invention may enhance the performance of certain optical devices, such as liquid crystal displays (e.g., color liquid crystal displays) by providing enhanced contrast ratio, faster response times, and/or lower operating voltage.

Claims (66)

1. A composition, comprising:

a polymeric network comprising the assembly of a plurality of polymer molecules, wherein each polymer molecule has the structure:

wherein n is at least 1, A and C are optionally substituted aromatic groups; B and D are absent, alkene, alkyne, heteroalkene, or heteroalkyne; and E 1 and E 2 can be the same or different and are intermolecular interacting groups,

wherein at least 50% of the polymer molecules are connected to an adjacent polymer molecule via at least one of the intermolecular interacting groups, and

wherein the polymeric network has a greater dichroic ratio than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

2. A composition as in claim 1 , wherein the polymer molecules are connected to an adjacent polymer molecule via a non-covalent bond.

3. A composition as in claim 2 , wherein the non-covalent bond is a hydrogen bond, ionic bond, dative bond, or Van der Waals interaction.

4. A composition as in claim 2 , wherein the non-covalent bond is a hydrogen bond.

5. A composition as in claim 1 , wherein the polymer molecules are connected to an adjacent polymer molecule via a covalent bond.

6. A composition as in claim 1 , wherein the polymer molecule is a polymer having a substantially rigid polymer backbone.

7. A composition as in claim 1 , wherein the polymer molecule is a poly(arylene), poly(arylenevinylene), poly(aryleneethylnylene), or substituted derivatives thereof.

8. A composition as in claim 1 , wherein the polymer molecule is poly(aryleneethylnylene).

9. A composition as in claim 1 , wherein E 1 and E 2 are groups capable of forming hydrogen bonds with an adjacent polymer molecule.

10. A composition as in claim 1 , wherein the polymer has the structure,

wherein R 1 and R 2 are 2-ethylhexyl, and R 3 is butyl.

11. A composition as in claim 1 , wherein at least 60% of the polymer molecules are connected to an adjacent polymer molecule via the at least one interacting group.

12. A composition as in claim 1 , wherein at least 70% of the polymer molecules are connected to an adjacent polymer molecule via the at least one interacting group.

13. A composition as in claim 1 , wherein at least 80% of the polymer molecules are connected to an adjacent polymer molecule via the at least one interacting group.

14. A composition as in claim 1 , wherein at least 90% of the polymer molecules are connected to an adjacent polymer molecule via the at least one interacting group.

15. A composition as in claim 1 , further comprising a host material with which the polymer network is mixed.

16. A composition as in claim 15 , wherein the host material comprises a liquid crystal.

17. A composition as in claim 1 , wherein the polymeric network has a dichroic ratio that is at least 10% greater than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

18. A composition as in claim 1 , wherein the polymeric network has a dichroic ratio that is at least 20% greater than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

19. A composition as in claim 1 , wherein the polymeric network has a dichroic ratio that is at least 30% greater than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

20. A composition as in claim 1 , wherein the polymeric network has a dichroic ratio that is at least 40% greater than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

21. A composition as in claim 1 , wherein the polymeric network has a dichroic ratio that is at least 50% greater than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

22. A composition as in claim 1 , wherein the polymeric network has a dichroic ratio that is at least 60% greater than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

23. A composition as in claim 1 , wherein the polymeric network has a dichroic ratio that is at least 70% greater than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

24. A composition, comprising:

a polymer having a substantially rigid polymer backbone; and

at least one intermolecular interacting group attached at or near a terminal end of the polymer, wherein the polymer has the structure,

wherein n is at least 1, A and C are optionally substituted aromatic groups; B and D are absent, alkene, alkyne, heteroalkene, or heteroalkyne; and E 1 and E 2 can the be the same or different and are interacting groups.

25. A composition as in claim 24 , wherein the polymer has the structure,

wherein R 1 and R 2 can be the same or different and are alkyl, heteroalkyl, aryl, heteroaryl, or substituted derivatives thereof.

26. A composition as in claim 25 , wherein the polymer has the structure,

wherein R 1 and R 2 are 2-ethylhexyl, and R 3 is butyl.

27. A method for increasing the dichroic ratio of a polymer molecule, comprising:

providing a host material and a plurality of polymer molecules with which the host material is mixed, wherein each polymer molecule comprises at least one intermolecular interacting group attached at or near a terminal end of the polymer molecule; and

allowing the at least one interacting group to interact with an adjacent polymer molecule to form a polymeric network, wherein the polymeric network has a greater dichroic ratio than the dichroic ratio of a polymer molecule essentially identical, but lacking the interacting group, under essentially identical conditions, and wherein the polymer molecule has the structure,

wherein n is at least 1, A and C are optionally substituted aromatic groups; B and D are absent, alkene, alkyne, heteroalkene, or heteroalkyne; and E 1 and E 2 can the be the same or different and are interacting groups.

28. A method as in claim 27 , wherein E 1 and E 2 are groups capable of forming hydrogen bonds with an adjacent polymer molecule.

29. A method as in claim 27 , wherein the polymer molecule has the structure,

wherein R 1 and R 2 can be the same or different and are alkyl, heteroalkyl, aryl, heteroaryl, or substituted derivatives thereof.

30. A method as in claim 27 , wherein the polymer has the structure,

wherein R 1 and R 2 are 2-ethylhexyl, and R 3 is butyl.

31. A composition as in claim 1 wherein the polymer molecule comprises the structure,

wherein G, H, I, and J are aromatic groups, d=1, 2, and d 1 =0, 1, such that when d 1 =0, d 2 =0 and when d 1 =1, d 2 =0, 1.

32. A composition as in claim 31 , wherein G and H can be the same or different and are:

optionally substituted, I and J may be the same or different and are:

optionally substituted,

wherein each Z 1 can be the same or different and Z 1 is O, S or NR, wherein R is hydrogen, alkyl, heteroalkyl, aryl, or heteroaryl, optionally substituted, and each Z 2 can be the same or different and Z 2 is halide, alkyl, heteroalkyl, aryl, or heteroaryl, optionally substituted.

33. A composition as in claim 1 , wherein the polymer has the structure,

wherein R 1 and R 2 are alkyl.

34. A method as in claim 27 , wherein the polymer has the structure,

wherein R 1 and R 2 are alkyl.

35. A composition, comprising:

a polymeric network comprising the assembly of a plurality of polymer molecules, wherein each polymer molecule comprises at least one intermolecular interacting group positioned at a terminal end of the polymer molecule,

wherein at least 50% of the polymer molecules are connected to an adjacent polymer molecule via the at least one intermolecular interacting group,

wherein the polymeric network has a greater dichroic ratio than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions, and

wherein the polymer molecules comprise the structure:

optionally substituted.

36. A composition, comprising:

a polymeric network comprising the assembly of a plurality of polymer molecules, wherein each polymer molecule has the structure:

wherein R 1 and R 2 can be the same or different and are alkyl, heteroalkyl, aryl, heteroaryl, or substituted derivatives thereof, n is at least 1, and E 1 and E 2 can be the same or different and are intermolecular interacting groups,

wherein at least 50% of the polymer molecules are connected to an adjacent polymer molecule via at least one of the intermolecular interacting group, and

wherein the polymeric network has a greater dichroic ratio than a dichroic ratio of an individual polymer molecule of the polymeric network, when the polymeric network and the individual polymer molecule are placed under essentially identical conditions.

Assignments (2)
CONFIRMATORY LICENSE Recorded Aug 6, 2012
From: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 028727/0421 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2009
From: SWAGER, TIMOTHY M.; HOOGBOOM, JOHAN T.V.
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 023256/0287 →
Continuity (3)
Provisional Application 60855966 · Nov 1, 2006
Provisional Application 61207859 · Dec 18, 2006
Related Publication 20100025630A1 · Feb 4, 2010