Mesogens

• US 7,238,831 B2
• Filed: 01/23/2002
• Issued: 07/03/2007
• Est. Priority Date: 01/23/2001
• Status: Expired due to Term

• Current Assignee: Southwest Research Institute
• Original Assignee: Southwest Research Institute
• Inventors: Hanson, Douglas P., Wellinghoff, Stephen T.
• Primary Examiner(s): OH, TAYLOR V
• Application Number:
  US10/056,121
• Publication Number:
  US 20020177727A1
• Time in Patent Office: 1,987 Days
• Field of Search: 560/109, 560/66, 560/19, 560/86, 428/1.1, 528/308
• US Class Current: 560/86
• CPC Class Codes: C09K 19/20 linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
• CPC Class Codes: C09K 19/2007 the chain containing -COO- or -OCO- groups
• CPC Class Codes: C09K 19/52 characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
• CPC Class Codes: C09K 2019/0448 the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
• CPC Class Codes: C09K 2019/2078 Ph-COO-Ph-COO-Ph
• CPC Class Codes: C09K 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
• CPC Class Codes: Y10S 585/935 Halogen-containing

Abstract

Novel platform mesogens, intermediates, and polymerizable mesogens made therefrom.

Claims

1. Mesogens having the following formula:

wherein

X is a polymerizable group,

Y consists essentially of an amino group;

R² is selected from the group consisting of hydrogen and a methyl group.

2. The mesogens of claim 1 wherein said polymerizable groups have polymerizable unsaturated carbon-carbon bond.

3. The mesogens of claim 1 wherein said polymerizable groups are selected from the group consisting of acryloyloxy alkoxy groups and methacryloyloxy alkoxy groups having alkyl moiety with from 2 to 12 carbon atoms.

4. The mesogens of claim 3 wherein said alkyl moiety consists essentially of from 2 to 12 carbons atoms and CH₂ groups optionally are substituted by groups selected from the group consisting of oxygen, sulfur, and ester groups;

provided that from 2 to 12 carbon atoms separate said oxygen from said ester groups.

5. The mesogens of claim 4, wherein said alkyl moiety consists essentially of a total of from 2 to 9 carbon atoms.

6. The mesogens of claim 4, wherein said alkyl moiety consists essentially of a total of from 2 to 6 carbon atoms.

7. The mesogens of claim 1 wherein X is cinnamoyloxy group.

8. Mesogens having the following formula

wherein

X is a polymerizable group selected from the group consisting of acryloyloxy alkoxy groups and methacryloyloxy alkoxy groups having alkyl moiety with from 2 to 12 carbon atoms;

Y consists essentially of an amino group;

R² is selected from the group consisting of alkyl groups having from about 1 to 6 carbon atoms and aryl groups; and

R¹ and R³are selected from hydrogen and a methyl group.

9. The mesogens of claim 8, wherein said alkyl moiety consists essentially of 2 to 12 carbons atoms and CH₂ groups optionally are substituted by groups selected from the group consisting of oxygen, sulfur, and ester groups;

provided that from 2 to 12 carbon atons separate said oxygen from said ester groups.

10. The mesogens of claim 9 wherein said alkyl moiety consists essentially of a total of from 2 to 9 carbon atoms.

11. The mesogens of claim 9 wherein said alkyl moiety consists essentially of a total of from 2 to 6 carbon atoms.

12. The mesogens of claim 8 wherein X is cinnamoyloxy group.

13. Mesogens having the following formula:

wherein X and Y independently are selected from the group consisting of spacer groups, polymerizable groups, and combinations thereof, wherein one or more members selected from the group consisting of X and Y have the following structure;

wherein Z is selected from the group consisting of spacer groups, terminal functionalities, polymerizable groups, and combinations thereof, said spacer groups being selected from the group consisting of H-(CH₂ )_n-O- groups, Cl(CH₂)_n-O- groups, Br(CH₂)_n-O- groups, wherein n is from about 2 to about 12 wherein the CH₂ groups independently can be substituted by oxygen, sulfur, or an ester group;

provided that from 2 to 12 carbons separate said oxygen or said ester group;

R² is selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms and aryl groups; and

R¹ to and R³ is selected from the group consisting of hydrogen and a methyl group.

14. The mesogens of claim 13 wherein n is from about 2 to 9.

15. The mesogens of claim 13 wherein n is from about 2 to 6.

16. The mesogens of claim 13 wherein said polymerizable groups have an alkyl moiety having a polymerizable unsaturated carbon-carbon bond.

17. The mesogens of claim 13 wherein said polymerizable groups have an alkyl moiety having a polymerizable unsaturated carbon-carbon bond.

18. The mesogens of claim 16 wherein said alkyl moiety has from 2 to 9 atoms.

19. The mesogens of claim 16 wherein said alkyl moiety has from 2 to 6 atoms.

20. The mesogens of claim 13 wherein R² is selected from the group consisting of methyl groups, t-butyl groups, isopropyl groups, secondary butyl groups, and phenyl groups.

21. The mesogens of claim 13 wherein R² is selected from the group consisting of methyl groups, t-butyl groups, isopropyl groups, secondary butyl groups, and phenyl groups.

22. The mesogens of claim 16 wherein R² is selected from the group consisting of methyl groups, t-butyl groups, isopropyl groups, secondary butyl groups, and phenyl groups.

23. The mesogens of claim 17 wherein R² is selected from the group consisting of methyl groups, t-butyl groups, isopropyl groups, secondary butyl groups, and phenyl groups.

24. The mesogens of claim 19 wherein R² is selected from the group consisting of methyl groups, secondary butyl groups, and phenyl groups.

25. The mesogens of claim 23 wherein R¹ and R³ are selected from the group consisting of hydrogen and a methyl group.

26. The mesogens of claim 24 wherein R¹ and R³ are selected from the group consisting of hydrogen and a methyl group.

27. The mesogens of claim 13 wherein one or more members selected from the group consisting of X and Y is a cinnamoyloxy group.

28. The mesogens of claim 20 wherein one or moreo members selected from the group consisting of X and Y is a cinnamoyloxy group.

29. The mesogens of claim 24 wherein one or more members selected from the group consisting of X and Y is a cinnamoyloxy group.