Mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method

• US 5,653,913 A
• Filed: 04/05/1996
• Issued: 08/05/1997
• Est. Priority Date: 08/31/1993
• Status: Expired due to Fees

• Current Assignee: Canon Ayutthaya Limited (Canon Inc.)
• Original Assignee: Canon Ayutthaya Limited (Canon Inc.)
• Inventors: Nakamura, Shinichi, Takiguchi, Takao, Iwaki, Takashi, Togano, Takeshi, Kosaka, Yoko
• Primary Examiner(s): Kelly, C. H.
• Application Number:
  US08/628,446
• Time in Patent Office: 487 Days
• Field of Search: 252/299.01, 252/299.6, 252/299.61, 252/299.62, 252/299.63, 252/299.66, 252/299.67, 252/299.65
• US Class Current: 252/299.01
• CPC Class Codes: C07C 69/76 Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 277/66 with aromatic rings or ring systems directly attached in position 2
• CPC Class Codes: C07D 285/12 1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
• CPC Class Codes: C09K 19/04 characterised by the chemical structure of the liquid crystal components , e.g. by a specific unit
• CPC Class Codes: C09K 19/12 at least two benzene rings directly linked, e.g. biphenyls
• CPC Class Codes: C09K 19/126 Compounds containing at least one asymmetric carbon atom
• CPC Class Codes: C09K 19/14 linked by a carbon chain
• CPC Class Codes: C09K 19/18 the chain containing carbon-to-carbon triple bonds, e.g. tolans
• 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 19/32 containing condensed ring systems, i.e. fused, bridged or spiro ring systems
• CPC Class Codes: C09K 19/322 Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
• CPC Class Codes: C09K 19/3405 the heterocyclic ring being a five-membered ring
• CPC Class Codes: C09K 19/3444 the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
• CPC Class Codes: C09K 19/3452 Pyrazine
• CPC Class Codes: C09K 19/3455 Pyridazine
• 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 19/3466 Pyrimidine with at least another heterocycle in the chain
• CPC Class Codes: C09K 19/3469 Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
• CPC Class Codes: C09K 19/3477 : the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom
• CPC Class Codes: C09K 19/3491 : having sulfur as hetero atom
• CPC Class Codes: C09K 19/3497 : the heterocyclic ring containing sulfur and nitrogen atoms
• CPC Class Codes: C09K 19/46 : containing esters
• CPC Class Codes: C09K 2019/3422 : the heterocyclic ring being a six-membered ring

Abstract

A mesomorphic compound of the formula (I) according to claim 1 characterized by having at least one CF₂ group between CH₂ groups in a specific alkoxy alkyl terminal group is suitable as a component for a liquid crystal composition providing improved response characteristics and a high contrast. A liquid crystal device is constituted by disposing the liquid crystal composition between a pair of substrates. The liquid crystal device is used as a display panel constituting a liquid crystal apparatus providing good display characteristics.

Claims

1. A liquid crystal composition, said liquid crystal composition having a chiral smectic phase and comprising at least two different compounds, at least one of which is a mesomorphic compound represented by the following formula (I):

space="preserve" listing-type="equation">C.sub.m H.sub.2m+1 O(CH.sub.2).sub.n -(CF.sub.2).sub.p -(CH.sub.2).sub.q --Y.sup.1 --A.sup.1 --R.sup.1 (I)

wherein R¹ denotes H, halogen, CN, or a linear or branched alkyl group having 1-30 carbon atoms or cyclized alkyl group having at most 6 carbon atoms, said alkyl group being capable of including at least one --CH₂ -- group which can be replaced with --O--, --S--, --CO--, --CH(Cl)--, --CH(CN)--, --CCH₃ (CN)--, --CH═

CH-- or --C≡

C-- provided that heteroatoms are not adjacent to each other and capable of including at least one H which can be replaced with F;

m, n, p and q independently denote an integer of 1-16 provided that m+n+p+q≦

19;

Y¹ denotes a single bond, --O--, --CO--, --COO--, --OCO--, --CH═

CH-- or --C≡

C--;

A¹ denotes --A² --, --A² --X¹ --A³ -- or --A² --X¹ --A³ --X² --A⁴ in which

A², A³ and A⁴ independently denote a divalent cyclic group selected from 1,4-phenylene capable of having one or two substituents comprising F, Cl, Br, CH₃, CF₃ or CN;

pyridine-2,5-diyl;

pyrimidine-2,5-diyl;

pyrazine-2,5-diyl;

pyridazine-3,6-diyl;

1,4-cyclohexylene;

1,3-dioxane-2,5-diyl;

1,3-dithiane-2,5-diyl;

thiophene-2,5-diyl;

thiazole-2,5-diyl;

thiadiazole-2,5-diyl;

benzoxazole-2,5-diyl;

benzoxazole-2,6-diyl;

benzothiazole-2,5-diyl;

benzothiazole-2,6-diyl;

quinoxaline-2,6-diyl;

quinoline-2,6-diyl;

2,6-naphthylene;

indan-2,5-diyl;

2-alkylindan-2,5-diyl having a linear or branched alkyl group having 1-18 carbon atoms;

indanone-2,6-diyl;

2-alkylindanone-2,6-diyl having a linear or branched alkyl group having 1-18 carbon atoms;

coumaran-2,5-diyl; and

2-alkylcoumaran-2,5-diyl having a linear or branched alkyl group having 1-18 carbon atoms; and

X^l and X² independently denote a single bond --COO--, --OCO--, --CH₂ O--, --OCH₂ --, --CH₂ CH₂ --, --CH═

CH-- or --C≡

C.

2. A liquid crystal composition according to claim 1, which comprises 1-80 wt. % of a mesomorphic compound of the formula (I).

3. A liquid crystal composition according to claim 1, which comprises 1-60 wt. % of a mesomorphic compound of the formula (I).

4. A liquid crystal composition according to claim 1, which comprises 1-40 wt. % of a mesomorphic compound of the formula (I).

5. A liquid crystal device, comprising a pair of substrates and a liquid crystal composition according to claim 1 disposed between the substrates.

6. A device according to claim 5, which further comprises an alignment control layer.

7. A device according to claim 6, wherein the alignment control layer has been subjected to uniaxial alignment treatment.

8. A device according to claim 5, wherein the liquid crystal composition is disposed in a thickness suppressing formation of a helical structure of liquid crystal molecules between the substrates.

9. A liquid crystal apparatus comprising a liquid crystal device according to claim 5.

10. An apparatus according to claim 9, wherein the liquid crystal device is used as a display device.

11. An apparatus according to claim 9, which further comprises a drive circuit for the liquid crystal device.

12. An apparatus according to claim 10, which further comprises a light source.

13. A display method, comprising:

providing a liquid crystal composition according to claim 1; and

controlling the alignment direction of liquid crystal molecules to effect display.