Octahydro binaphthyl-based chiral compound-containing liquid-crystal composition and optical element

Patent metadata

Field	Value
Publication number	US-9458125-B2
Application number	US-201314649917-A
Country	US
Kind code	B2
Filing date	Dec 12, 2013
Priority date	Dec 17, 2012
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

A liquid-crystal composition is composed of at least one chiral compound represented by general formula (K1) or (K2) and at least one achiral liquid-crystal component:

(wherein, in formulas (K1) and (K2), R k1 is, for example, alkyl having 1 to 5 carbons, R k2 is, for example, alkyl having 1 to 20 carbons, ring A k1 is, for example, 1,4-phenylene, X k1 is, for example, a single bond, Y k1 is, for example, —(CH 2 ) n —, n is an integer from 0 to 20, Z k1 is, for example, a single bond, mk1 is, for example, an integer from 2 to 4, and nk1 and nk2 are, for example, an integer from 0 to 2).

First claim

What is claimed is:

1. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K1) or (K2) and at least one achiral liquid-crystal component:

wherein, in formulas (K1) and (K2),
R k1 is halogen, cyano, —SF 5 or alkyl having 1 to 5 carbons, at least one of —CH 2 — in R k1 may be replaced by —O—, and at least one of hydrogen in R k1 may be replaced by halogen;
R k2 is halogen, cyano, —SF 5 or alkyl having 1 to 20 carbons, at least one of —CH 2 — in R k2 may be replaced by —O—, and at least one of hydrogen in R k2 may be replaced by halogen;
ring A k1 is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, tetrahydropyran-3,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl or 1,4-bicyclo-(2,2,2)-octylene, and at least one of hydrogen in the rings may be replaced by halogen;
X k1 is a single bond, —O—, —CO—, —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH═CH—, —CF 2 CF 2 —, —CF═CF— or —C≡C—;
Y k1 is a single bond or —(CH 2 ) n —, and n is an integer from 1 to 20;
Z k1 is a single bond or alkylene having 1 to 10 carbons, at least one of —CH 2 — in Z k1 may be replaced by —O—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and at least one of hydrogen in Z k1 may be replaced by halogen;
mk1 is an integer from 2 to 4; nk1 and nk2 is an integer from 0 to 2; and

when a plurality of R k1 , R k2 , A k1 , A k2 , X k1 , Y k1 , Z k1 , mk1, nk1 or nk2 exist, the plurality may be identical or different each other.

2. A liquid-crystal composition, comprising at least one chiral compound selected from compounds represented by general formulas (K1-1) to (K1-6) and at least one achiral liquid-crystal component:

wherein, in formulas (K1-1) to (K1-6),
R k1 is halogen, cyano, —SF 5 or alkyl having 1 to 5 carbons, at least one of —CH 2 — in R k1 may be replaced by —O—, and at least one of hydrogen in R k1 may be replaced by halogen;
R k2 is halogen, cyano, —SF 5 or alkyl having 1 to 20 carbons, at least one of —CH 2 — in R k2 may be replaced by —O—, and at least one of hydrogen in R k2 may be replaced by halogen;
ring A k1 is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, tetrahydropyran-3,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl or 1,4-bicyclo-(2,2,2)-octylene, and at least one of hydrogen in the rings may be replaced by halogen;
Y k1 is a single bond or —(CH 2 ) n —, and n is an integer from 1 to 20;
Z k1 is a single bond or alkylene having 1 to 10 carbons, at least one of —CH 2 — in Z k1 may be replaced by —O—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C— and at least one of hydrogen in Z k1 may be replaced by halogen;
nk1 and nk2 are an integer from 0 to 2; and
when a plurality of R k1 , R k2 , A k1 , A k2 , Y k1 , Z k1 , nk1 or nk2 exist, the plurality may be identical or different each other.

3. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K2-1) or (K2-2) and at least one achiral liquid-crystal component:

wherein, in formulas (K2-1) to (K2-2),
R k1 is halogen, cyano, —SF 5 or alkyl having 1 to 5 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, and at least one of hydrogen in the alkyl may be replaced by halogen;
R k2 is halogen, cyano, —SF 5 or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, and at least one of hydrogen in the alkyl may be replaced by halogen;
ring A k1 is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, tetrahydropyran-3,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl or 1,4-bicyclo-(2,2,2)-octylene, and at least one of hydrogen in the rings may be replaced by halogen;
Y k1 is a single bond or —(CH 2 ) n —, and n is an integer from 1 to 20;
Z k1 is a single bond or alkylene having 1 to 10 carbons, at least one of —CH 2 — in the alkylene may be replaced by —O—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and at least one of hydrogen in the alkylene may be replaced by halogen;
nk1 or nk2 is an integer from 0 to 2; and

when a plurality of R k1 , R k2 , A k1 , A k2 , Y k1 , nk1 or nk2 exist, the plurality may be identical or different each other.

4. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K1-1-1), (K1-1-2), (K1-2-1), (K1-2-2), (K1-4-1), (K1-4-2), (K1-5-1) or (K1-5-2) and at least one achiral liquid-crystal component:

wherein, in the formulas,
R k1 is hydrogen, halogen, cyano or alkyl having 1 to 5 carbons, and at least one of hydrogen in the alkyl may be replaced by halogen;
R k2 is hydrogen, halogen, cyano or alkyl having 1 to 20 carbons, and at least one of hydrogen in the alkyl may be replaced by halogen;
ring A k1 is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, tetrahydropyran-3,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and at least one of hydrogen in the rings may be replaced by halogen;
n is an integer from 0 to 10;
Z k1 is a single bond, alkylene having 1 to 10 carbons, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—;
X k1 , X k2 , X k3 and X k4 are independently hydrogen or fluorine, wherein three or more fluorine cannot exist at the same time in X k1 , X k2 , X k3 and X k4 ;
nk1 or nk2 is an integer from 0 to 2; and

when a plurality of R k1 , R k2 , A k1 , Z k1 , nk1 or nk2 exist, the plurality may be identical or different each other.

5. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K2-1-1), (K2-1-2), (K2-2-1), (K2-2-2) or (K2-2-3) and at least one achiral liquid-crystal component:

wherein, in formulas (K2-1-1) to (K2-2-3),
R k1 is hydrogen, halogen, cyano or alkyl having 1 to 5 carbons, and at least one of hydrogen in the alkyl may be replaced by halogen;
R k2 is hydrogen, halogen, cyano or alkyl having 1 to 20 carbons, and at least one of hydrogen in the alkyl may be replaced by halogen;
ring A k1 is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, tetrahydropyran-3,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and at least one of hydrogen in the rings may be replaced by halogen;
n is an integer from 0 to 10;
Z k1 is a single bond, alkylene having 1 to 10 carbons, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—;
X k1 , X k2 , X k3 and X k4 are independently hydrogen or fluorine, wherein three or more fluorine cannot exist at the same time in X k1 , X k3 and X k4 ;
nk1 or nk2 is an integer from 0 to 2; and when

a plurality of R k1 , R k2 , A k1 , Z k1 , nk1 or nk2 exist, the plurality may be identical or different each other.

6. The liquid-crystal composition according to claim 1 , containing at least one compound represented by general formula (1-A) is contained in the achiral liquid-crystal component:

wherein, in genera

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Sago Koki
• Yamamoto Shin-Ichi

Classifications

• C07D319/06 Primary

  not condensed with other rings · CPC title

• C09K19/588

  Heterocyclic compounds · CPC title

• C09K19/20

  linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers} · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C09K2019/325

  containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin) · CPC title