Fluorine-containing chiral smectic liquid crystals

• US 4,886,619 A
• Filed: 05/29/1987
• Issued: 12/12/1989
• Est. Priority Date: 06/30/1986
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Inventors: Janulis, Eugene P.
• Primary Examiner(s): Gron, Teddy S.
• Application Number:
  US07/053,551
• Time in Patent Office: 928 Days
• Field of Search: 252/299.01, 252/299.5, 252/299.65, 252/299.67, 252/299.6, 252/299.61, 252/299.62, 252/299.63, 252/299.64, 252/299.66, 252/299.68 , 252/299.1, 252/299.4, 350/350 R, 350/350 S, 350/349, 560/1, 560/65, 560/73, 560/100, 560/105, 560/106, 560/109, 560/125, 560/126, 560/8, 560/59, 560/102, 560/256, 560/257, 560/107, 560/108, 560/111, 560/60, 560/61, 560/62, 560/144 , 560/138, 560/8, 570/129, 546/326, 546/322, 546/315, 546/270, 546/272, 260/550, 568/328, 568/329, 568/331, 568/325, 568/632, 568/635, 568/642, 568/644, 568/659, 568/664, 544/240, 544/239, 544/335, 544/295, 544/296, 544/298, 544/315, 544/318
• US Class Current: 252/299.1
• CPC Class Codes: C07D 213/80 in position 3
• CPC Class Codes: C07D 237/14 Oxygen atoms
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• 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 19/22 linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
• CPC Class Codes: C09K 19/28 linked by a chain containing carbon and sulfur atoms as chain links, e.g. thioesters
• CPC Class Codes: C09K 19/322 Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
• CPC Class Codes: C09K 19/3441 having nitrogen as hetero atom
• CPC Class Codes: C09K 19/3463 Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
• CPC Class Codes: C09K 19/3469 Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
• CPC Class Codes: C09K 19/40 containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals

Abstract

Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.

Claims

1. Compounds comprising a fluorocarbon terminal portion represented by the formula -DC_q F_2q X where X is hydrogen or fluorine, q is 1 to 20, and D is ##STR95## --O--(CH₂)_r --, --(CH₂)_r --, --OSO₂ --, --SO₂ --, --SO₂ --(CH₂)_r --, --O(CH₂)_r --O(CH₂)_r'"'"' --, ##STR96## where r and r'"'"' are independently 1 to 20, and p is 0 to 4, and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture and said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.

2. The compounds of claim 1 wherein said compounds have a suppressed cholesteric phase.

4. The compound of claim 1 represented by the formula ##STR105##

5. A liquid crystal display device comprising two bounding plates, the inside surfaces of which have electrodes applied thereto and at least one of which is transparent, said device containing a compound of claim 1 between said bounding plates.

6. The device of claim 5 wherein said device is surface-stabilized.

7. The device of claim 5 wherein said device is non-surface-stabilized.

8. The device of claim 5 wherein said device is optically addressable.

9. The device of claim 5 further comprising at least one pleochroic dye in admixture with said compound.

10. A mixture of at least one compound of claim 1 and an additional liquid crystal material.

3. The chiral smectic or latent chiral smectic liquid crystal compounds represented by the formula ##STR97## where M, N, and P are each independently ##STR98## a, b, and c are each independently zero or an integer of from 1 to 3 with the proviso that the sum of a+b+c be at least 2;

each A and B are independently nil, ##STR99## --CH═

N--, --CH₂ --O--, ##STR100## --O--, --CH₂ CH₂ --, --CH═

CH--, or --C.tbd.C--;

each X, Y and Z are independently --H, --Cl, --F, --OCH₃, --CH₃, --NO₂, --OH, --Br, --I, or --CN;

each l, m, and n are independently zero or an integer of 1 to 4;

D is ##STR101## --O--(CH₂)_r --, --(CH₂)_r --, --OSO₂ --, --SO₂ --, --SO₂ --(CH₂)_r --, --O(CH₂)_r --O(CH₂)_r'"'"' --, ##STR102## where r and r'"'"' are independently 1 to 20, and p is 0 to 4;

R is --OC_q H_2q --OC_q, H_{2q'"'"'+1'"'"'} --C_q H_2q --O--C_q'"'"' H_2q'"'"'+1, --C_q H_2q --R'"'"', --O--C_q H_q H_2q --R'"'"', ##STR103## where R'"'"' is --Cl, --F, --CF₃, --NO₂, --CN, --H, ##STR104## and q and q'"'"' are independently 1 to 20 with the proviso that R is chiral;

R_f is --C_q F_2q --X or --C_q F_2q --O--C_q'"'"' F_2q'"'"' --X where X is H or F and q and q'"'"' are independently 1 to 20.