Liquid crystalline material

• US 5,560,864 A
• Filed: 02/22/1995
• Issued: 10/01/1996
• Est. Priority Date: 02/23/1994
• Status: Expired due to Term

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Goulding, Mark
• Primary Examiner(s): WU, SHEAN CHIU
• Application Number:
  US08/392,349
• Time in Patent Office: 587 Days
• Field of Search: 252/299.01, 252/299.61, 252/299.66, 252/299.63, 252/299.67, 252/299.64, 252/299.65, 359/103, 359/106, 526/318.1, 526/319
• US Class Current: 252/299.01
• CPC Class Codes: C07C 43/215 having unsaturation outside the six-membered aromatic rings
• CPC Class Codes: C07C 43/225 containing halogen
• CPC Class Codes: C07C 69/92 with etherified hydroxyl groups
• CPC Class Codes: C07D 303/22 with monohydroxy compounds
• CPC Class Codes: C08G 59/22 Di-epoxy compounds
• CPC Class Codes: C09K 13/00 Etching, surface-brightening or pickling compositions for glass C03C15/00, C03C25/66; for mortars, concrete, artificial or natural stone or ceramics C04B41/5338 ; for metallic material C23F, C23G1/00, C25F1/00; for semi-conductors H01L
• CPC Class Codes: C09K 19/126 Compounds containing at least one asymmetric carbon atom
• CPC Class Codes: C09K 19/2021 Compounds containing at least one asymmetric carbon atom
• CPC Class Codes: C09K 19/2028 containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3
• CPC Class Codes: C09K 19/42 Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40

Abstract

A liquid crystalline material in the form of an anisotropic gel containing a polymerized monotropic or enantiotropic liquid crystalline material and a low-molecular weight liquid crystalline material, wherein the polymerized material a) forms a permanently oriented network in the low-molecular weight liquid crystalline material b), wherein a) is obtained by (co)-polymerization of a chiral polymerizable compound, and a display cell with such a material. Also, novel bifunctional reactive chiral compounds, novel chiral vinylethers and (co)-polymerizable precursor materials.

Claims

1. A copolymerizable precursor material comprising at least one bifunctional reactive achiral compound of formula VI

View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)

2. A copolymerizable precursor material according to claim 1, wherein in at least one reactive chiral compound of formula I

3. A copolymerizable precursor material according to claim 1, wherein in at least one compound of formula I R⁴ is a vinyl ether radical of formula CH₂ ═

CH--O--.

4. A copolymerizable precursor of claim 1, wherein the monoreactive chiral compound is selected from one of the formulae III to V ##STR56## wherein R⁴, X, P, R⁵ and u have the meaning given, A³ and A⁴ are each independently optionally fluorinated 1,4-phenylene in which one or two CH groups may be replaced by N or 1,4-cyclohexylene in which one or two non-adjacent CH₂ groups may be replaced by O,

Z² is --CO--O, --O--CO--, --OCH₂ --, --CH₂ O--, --CH₂ CH₂ --, --C≡

C--, --C≡

C--C≡

C-- or a single bond, and

p is 0, 1 or 2,

R⁰ is CH₃, C₆ H₅, F, Cl, CN or CF₃,

Q¹ and Q² are each, independently, CO or a single bond,

n is 0, 1 or 2, and

m is an integer of 1 to 10.

5. A cholesteric film obtained by the steps comprising

a) ordering the copolyermizable precursor material of claim 1 in the monomeric state in the presence of a UV initiator and optionally an additive, and

b) in situ UV polymerizing the resulting ordered precursor material.

6. The copolymerizable precursor of claim 4, wherein R^o is CH₃ or C₆ H₅.

7. The copolymerizable precursor of claim 1, wherein, in the chiral compound of formula I, C* is a group selected from one of the following formulae:

##STR57## wherein R^o is CH₃, C₆ H₅, F, Cl, CN or CF₃,

Q¹ and Q² are each, independently CO or a single bond,

n is 0, 1 or 2,

m is an integer from 1 to 10,

o is 1, 2 or 3, and

* denotes a chiral center.

8. The copolymerizable precursor of claim 7, wherein C* is a group of formula (2) or (4).

9. The copolymerizable precursor of claim 1, wherein, in the achiral compound of formula VI and the chiral compound of formula I, MG¹ and MG² are, independently, selected from groups of the following formulae:

##STR58## wherein X is CN or F and r is 0, 1 or 2.

10. The copolymerizable precursor of claim 4, wherein the chiral compound is of the formula (III), wherein n is 1, m is 2 and R^o is CH₃.

11. The copolymerizable precursor of claim 1, wherein the chiral compound is present in a quantity of 1-50% by weight.

12. The copolymerizable precursor of claim 1, wherein the chiral compound is present in a quantity of 2-10% by weight.

13. A monofunctional reactive compound of formula IIIa ##STR59## in which R⁴ is CH₂ ═

CW--COO--, ##STR60## HWN--, CH₂ ═

CH--, CH₂ ═

CH--O-- or HS--CH₂ --(CH₂)_m --COO-- with W being H, Cl or alkyl with 1-5 C atoms and m being 1-7,

P is alkylene with 1 to 12 C atoms, optionally, with one or more non-adjacent CH₂ groups replaced by --O--,

X is --O--, --S--, --COO--, --OCO-- or a single bond,

u is 0 or 1,

A³ is optionally fluorinated 1,4-phenylene in which one or two CH groups may be replaced by N or 1,4-cyclohexylene in which one or two non-adjacent CH₂ groups may be replaced by O,

Z² is --CO--O--, --O--CO--, --OCH₂ --, --CH₂ O--, --CH₂ CH₂ --, --C≡

C--, --C≡

C--C≡

C--, or a single bond,

n is 0 or an integer of 1 to 20,

p is 1 or 2, and

m is an integer of from 2 to 10.

14. The monofunctional reactive compound of claim 13, in which n is 1 and m is 2.