Mesogenic stabilizers

• US 8,349,210 B2
• Filed: 08/08/2011
• Issued: 01/08/2013
• Est. Priority Date: 06/27/2008
• Status: Active Grant

• Current Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Original Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Inventors: Xu, Ruisong, Dai, Xiao-Man, Kumar, Anil, He, Meng, Li, Chenguang, Yoest, Rachael L.
• Primary Examiner(s): Visconti, Geraldina
• Application Number:
  US13/204,835
• Publication Number:
  US 20120003401A1
• Time in Patent Office: 519 Days
• Field of Search: 252/299.01, 252/299.5, 252/299.6, 252/299.61, 252/299.62, 428/1.1, 428/1.3, 546/188, 546/222, 549/415, 549/416, 560/59, 560/61, 560/81, 349/1, 349/56, 349/182
• US Class Current: 252/299.01
• CPC Class Codes: C07D 211/48 having an acyclic carbon atom attached in position 4
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C09K 19/3483 the heterocyclic ring being a non-aromatic ring
• CPC Class Codes: C09K 19/54 Additives having no specific mesophase characterised by their chemical composition
• CPC Class Codes: C09K 19/60 Pleochroic dyes
• 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 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
• CPC Class Codes: C09K 2323/03 Viewing layer characterised by chemical composition

Abstract

The present invention relates to compounds represented by the following Formula I,

in which R¹-R⁶ can each independently be selected from hydrogen or hydrocarbyl (e.g., methyl); L¹ is a divalent linking group, such as a bond or —OC(O)—R⁸—C(O)O—, where R⁸ can be divalent hydrocarbyl (e.g., —CH₂CH₂—); each L² independently represents a flexible segment, such as divalent linear or branched C₁-C₂₅ alkyl; each L³ independently represents a rigid segment including, for example, optionally substituted phenylen-1,4-diyl groups; t is from 1 to 4; m and p are each independently from 0 to 4 for each t, provided that the sum of m and p is at least 1 for each t; and E can be hydrogen or hydrocarbyl. The present invention also relates to compositions, such as liquid crystal compositions, and articles, such as optical elements, that include the compound represented by Formula I.

Claims

1. A compound represented by the following Formula I,

2. The compound of claim 1, wherein,

R¹ is selected from hydrogen, linear or branched C₁-C₂₅ alkyl, linear or branched C₂-C₂₅ alkenyl, each optionally interrupted with a group selected from cyclohexylen-1,4-diyl, —

O—

, —

C(O)—

, and —

Si(CH₃)₂—

, and each optionally having at least one hydrogen replaced with F,

R², R³, R⁴ and R⁵ are each independently selected from linear or branched C₁-C₁₀ alkyl,

R⁶ is selected from hydrogen, linear or branched C₁-C₂₅ alkyl, linear or branched C₂-C₂₅ alkenyl, each optionally interrupted with a group selected from cyclohexylen-1,4-diyl, —

O—

, —

C(O)—

, and —

Si(CH₃)₂—

, and each optionally having at least one hydrogen replaced with F,

R⁷ and R⁸ of L¹ are each independently selected from divalent linear or branched C₁-C₂₅ alkyl, divalent linear or branched C₂-C₂₅ alkenyl, divalent C₃-C₁₂ cycloalkyl, divalent C₃-C₁₂ heterocycloalkyl, divalent aryl, and divalent heteroaryl,

m is at least 1 for at least one t,

L² is, independently for each m, selected from divalent linear or branched C₁-C₂₅ alkyl optionally interrupted with at least one of —

O—

, —

C(O)O—

, and —

OC(O)O—

,

p is at least 1 for at least one t,

Z is, independently for each v, selected from a bond, —

O— and

—

C(O)O—

,

the divalent rings,

3. The compound of claim 2, wherein,

R¹ is selected from hydrogen, or linear or branched C₁-C₈ alkyl,

R², R³, R⁴ and R⁵ are each independently selected from linear or branched C₁-C₆ alkyl,

R⁶ is selected from hydrogen, and linear or branched C₁-C₈ alkyl,

L¹ is selected from a bond or the divalent linking group represented by Formula IId, wherein R⁸ is divalent linear or branched C₁-C₆ alkyl,

L² is, independently for each m, selected from divalent linear or branched C₁-C₁₀ alkyl optionally interrupted with at least one of —

O—

, —

C(O)O—

, and —

OC(O)O—

, and

E is selected from hydrogen and linear or branched C₁-C₁₀ alkyl optionally interrupted with at least one of —

O— and

—

C(O)O—

.

4. The compound of claim 1, wherein L¹ is the divalent linking group represented by Formula IId, wherein R⁸ is divalent linear or branched C₁-C₆ alkyl.

5. The compound of claim 1, wherein E is substituted with at least one group represented by the following formula,

6. The compound of claim 1, wherein at least one of:

(i) E is substituted with at least one group selected from,

a group represented by the following Formula G,

7. The compound of claim 1, wherein E is substituted with at least one group represented by the following Formula H,

8. The compound of claim 3, wherein each L³ is independently selected from the following formulas,

9. The compound of claim 1, wherein said compound is selected from at least one compound represented by the following Formulas VIII(A) through VIII(N),

10. The compound of claim 1, wherein the compound is a mesogenic compound.

11. A liquid crystal composition comprising the compound of claim 1.

12. The liquid crystal composition of claim 11, further comprising at least one of a photochromic compound, a dichroic compound, and a photochromic-dichroic compound.

13. The liquid crystal composition of claim 12, wherein said photochromic compound or said photochromic-dichroic compound is selected from indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, diarylalkenylethenes, non-thermally reversible photochromic compounds, and mixtures thereof.

14. An article of manufacture comprising the compound of claim 1.

15. The article of manufacture of claim 14, wherein said article of manufacture is an optical element comprising:

a substrate; and

a layer on at least a portion of a surface of said substrate, wherein said layer comprises the compound of claim 1.

16. The optical element of claim 15, wherein said layer is at least partially aligned by exposing at least a portion of said layer to at least one of a magnetic field, an electric field, linearly polarized radiation, and shear force.

17. The optical element of claim 15, wherein said layer comprises a liquid crystal phase having at least one of a nematic phase, a smectic phase, or a chiral nematic phase.

18. The optical element of claim 15, wherein said optical element is selected from an ophthalmic element, a display element, a window, a mirror, and a liquid crystal cell element.

19. The ophthalmic element of claim 18, wherein said ophthalmic element is selected from a corrective lens, a non-corrective lens, a contact lens, an intra-ocular lens, a magnifying lens, a protective lens, and a visor.

20. The article of manufacture of claim 14, wherein said article of manufacture is a liquid crystal cell comprising:

a first substrate having a first surface;

a second substrate having a second surface, said first surface of said first substrate and said second surface of said second substrate being in spaced opposition from each other, and together defining a space there-between; and

a liquid crystal composition residing within at least a portion of said space, said liquid crystal composition comprising the compound of claim 1.

21. A method of forming an ophthalmic element comprising:

forming a liquid crystal composition comprising the compound of claim 1;

applying said liquid crystal composition to at least a portion of a substrate;

at least partially aligning at least a portion of the liquid crystal composition applied to said substrate, thereby forming an at least partially aligned liquid crystal composition; and

curing, at least partially, the aligned liquid crystal composition.