Liquid crystal compound, liquid crystal composition, composite material with encapsulated liquid crystal, and liquid crystal display device using same

Patent metadata

Field	Value
Publication number	US-10570334-B2
Application number	US-201615557798-A
Country	US
Kind code	B2
Filing date	Mar 2, 2016
Priority date	Mar 12, 2015
Publication date	Feb 25, 2020
Grant date	Feb 25, 2020

Abstract

Shown is a bimesogenic compound having high solubility in a liquid crystal compound, a liquid crystal composition, a chiral dopant, an additive including an antioxidant or an ultraviolet light absorber, and a polymerizable liquid crystal compound, each of which is used in other bimesogenic compounds or a liquid crystal display device, while maintaining desired physical properties.
A compound is represented by formula (1), a liquid crystal composition contains the compound, conjugate fibers with an encapsulated liquid crystal obtained from the liquid crystal composition, and a liquid crystal display device is obtained from the conjugate fibers with the encapsulated liquid crystal.

MG 1 -Z a -Sp-Z b -MG 2   (1)

First claim

What is claimed is:

1. A compound, represented by formula (1):
MG 1 -Z a -Sp-Z b -MG 2   (1)

wherein, in formula (1), MG 1 and MG 2 are each independently a mesogenic group;
Z a and Z b are independently a single bond or alkylene having 1 to 4 carbons, and in the Z a and the Z b , at least one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and at least one piece of hydrogen may be replaced by fluorine;
Sp has an achiral structure represented by formula (sp-1):
-α-X-α-  (sp-1)

wherein, in formula (sp-1), α is each independently straight-chain alkylene having 1 to 20 carbons, and in the α, at least one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and at least one piece of hydrogen may be replaced by fluorine;
X is represented by formula (I), formula (II) or formula (III):

wherein, in formula (I), Ra is a hydroxyl group or alkyl having 1 to 10 carbons, and in the Ra, at least one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and at least one piece of hydrogen may be replaced by fluorine;
in formula (II), Rb and Rc are each independently fluorine, chlorine or alkyl having 1 to 10 carbons, and in the Rb and the Rc, at least one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one piece of —(CH 2 ) 2 — may be replace by —CH═CH— or —C≡C—, and at least one piece of hydrogen may be replaced by fluorine; and
in formula (III), Q is an oxygen atom, a sulfur atom or alkylidene having 1 to 10 carbons, and in the Q, at least one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and at least one piece of hydrogen may be replaced by fluorine.

2. The compound according to claim 1 , wherein, in formula (1), MG 1 and MG 2 are represented by formula (IV):
A 1 -Z 1 m A 2 -Z 2 n A 3 -Z 3 q A 4 -Z 4 r -Rd  (IV)

wherein, in formula (IV), Rd is independently —CN, —NCS, —C≡C—CN, —SF 5 , fluorine, chlorine or straight-chain alkyl having 1 to 20 carbons, and in the Rd, at least one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, and at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—; A 1 , A 2 , A 3 and A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, cyclohexene-1,4-diyl, naphthalene-2,6-diyl, and in the rings, one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, and at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —CH═N—, and in the rings, at least one piece of hydrogen may be replaced by fluorine, chlorine, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F;
Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond or alkylene having 1 to 4 carbons, and in the Z 1 , the Z 2 , the Z 3 and the Z 4 , at least one piece of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and at least one piece of hydrogen may be replaced by fluorine; and
m, n, q and r are independently 0 or 1, and a sum of m, n, q and r is 2, 3 or 4.

3. The compound according to claim 2 , wherein, in formula (IV), Rd is fluorine, chlorine or straight-chain alkyl having 1 to 10 carbons, straight-chain alkenyl having 2 to 10 carbons, straight-chain alkoxy having 1 to 9 carbons, straight-chain alkoxyalkyl having 2 to 9 carbons, straight-chain alkenyloxy having 3 to 9 carbons, straight-chain polyfluoroalkyl having 1 to 10 carbons, straight-chain polyfluoroalkoxy having 1 to 9 carbons or straight-chain polyfluoroalkenyl having 2 to 10 carbons;
A 1 , A 2 , A 3 and A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, cyclohexene-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or naphthalene-2,6-diyl, and in the rings, at least one piece of hydrogen may be replaced by fluorine, chlorine, —CF 3 or —CHF 2 ; and
Z 1 , Z 2 and Z 4 are independently a single bond, —(CH 2 ) 2 —, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH—CH—, —CF—CF—, —C≡C—, —CH 2 CO—, —COCH 2 —, —CH 2 SiH 2 —, —SiH 2 CH 2 —, —(CH 2 ) 2 COO—, —OCO(CH 2 ) 2 —, —(CH 2 ) 2 CF 2 O—, —OCF 2 (CH 2 ) 2 —, —(CH 2 ) 3 O—, —O(CH 2 ) 3 — or —(CH 2 ) 4 —.

4. The compound according to claim 1 , wherein, in formula (1), Z a and Z b are independently a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CF═CF—, —CH 2 CO—, —C≡C—, —COCH 2 —, —CH 2 SiH 2 — or —SiH 2 CH 2 —;
in formula (sp-1), α is straight-chain alkylene having 1 to 10 carbons, and in the α, at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and at least one piece of hydrogen may be replaced by fluorine;
in formula (I), Ra is a hydroxyl group, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, alkoxy having 1 to 4 carbons, alkoxyalkyl having 2 to 4 carbons, alkenyloxy having 3 to 4 carbons, polyfluoroalkyl having 1 to 5 carbons, polyfluoroalkoxy having 1 to 4 carbons or polyfluoroalkenyl having 2 to 5 carbons;
in formula (II), Rb and Rc are each independently fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, alkoxy having 1 to 4 carbons, alkoxyalkyl having 2 to 4 carbons, alkenyloxy having 3 to 4 carbons, polyfluoroalkyl having 1 to 5 carbons, polyfluoroalkoxy having 1 to 4 carbons or polyfluoroalkenyl having 2 to 5 carbons; and
in formula (III), Q is an oxygen atom or alkylidene having 1 to 5 carbons.

5. The compound according to claim 4 , wherein, in formula (1), Z a and Z b are independently a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH═CH—, —CF═CF— or —C≡C—; and
in formula (sp-1), α is straight-chain alkylene having 1 to 10 carbons;
in formula (I), Ra is alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons or polyfluoroalkyl having 1 to 5 carbons;
in formula (II), Rb and Rc are each independently fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons or polyfluoroalkyl having 1 to 5 carbons; and
in formula (III), Q is an oxygen atom or alkylidene having 1 to 3 carbons.

6. The compound according to claim 1 , wherein, in formula (1), MG 1 and MG 2 are represented by formula (IV-1):

wherein, Rd is independently —CN, —NCS, —C≡C—CN, —SF 5 , fluorine, chlorine, straight-chain alkyl having 1 to 6 carbons, straight-chain alkenyl having 2 to 6 carbons, straight-chain alkoxy having 1 to 5 carbons, straight-chain polyfluoroalkyl having 1 to 6 carbons, straight-chain polyfluoroalkoxy having 1 to 5 carbons or straight-chain polyfluoroalkenyl having 2 to 6 carbons;
A 11 and A 31 are 1,4-cyclohexylene or 1,4-phenylene;
Y 21 , Y 22 , Y 23 , Y 41 , Y 42 and Y 43 are independently hydrogen, fluorine, —CF 3 or —CF 2 H;
Z 11 , Z 21 , Z 31 and Z 41 are independently a single bond, —(CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH═CH—, —CF═CF—, or —C≡C—; and
s, t, u and v are independently 0, 1 or 2, and a sum of s, t and u is 2, 3 or 4, in which t is 1 without exception, and when any one of s, t, u and v is 2, a plurality of ring structures may be an identical group or a different group, and a plurality of Z 11 , Z 21 , Z 31 and Z 41 may be an identical group or a different group.

7. The compound according to claim 1 , wherein, in formula (1), MG 1 and MG 2 are represented by formulas (IV-1-1-1) to

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Sawada Michiko
• Sasada Yasuyuki

Classifications

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title

• C09K19/54

  Additives having no specific mesophase {characterised by their chemical composition} · CPC title

• C07C2602/44

  the bicyclo ring system containing eight carbon atoms · CPC title

• C07C69/94

  of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings · CPC title

• C09K2019/122

  Ph-Ph · CPC title