LIQUID CRYSTAL COMPOUND, LIQUID CRYSTAL COMPOSITION, COMPOSITE MATERIAL WITH ENCAPSULATED LIQUID CRYSTAL, AND LIQUID CRYSTAL DISPLAY DEVICE USING SAME

• US 20180051210A1
• Filed: 03/02/2016
• Published: 02/22/2018
• Est. Priority Date: 03/12/2015
• Status: Active Grant

• Current Assignee: JNC Corporation (Chisso Corporation), JNC Petrochemical Corporation (Chisso Corporation)
• Original Assignee: JNC Corporation (Chisso Corporation), JNC Petrochemical Corporation (Chisso Corporation)
• Inventors: SAWADA, Michiko, SASADA, Yasuyuki
• Granted Patent: US 10,570,334 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 13/28 Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
• CPC Class Codes: C07C 255/55 containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2602/44 the bicyclo ring system containing eight carbon atoms
• CPC Class Codes: C07C 313/16 having sulfur atoms of sulfenic groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 319/06 from sulfides, hydropolysulfides or polysulfides
• CPC Class Codes: C07C 331/28 having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 381/00 Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
• CPC Class Codes: C07C 43/225 containing halogen
• CPC Class Codes: C07C 43/23 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 43/315 containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
• CPC Class Codes: C07C 47/198 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07C 49/175 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07C 49/782 polycyclic
• CPC Class Codes: C07C 69/34 Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
• CPC Class Codes: C07C 69/593 Dicarboxylic acid esters having only one carbon-to-carbon double bond
• CPC Class Codes: C07C 69/757 having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
• 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: C07C 69/94 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 Class Codes: C07D 309/06 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 319/06 : not condensed with other rings
• CPC Class Codes: C09K 19/12 : at least two benzene rings directly linked, e.g. biphenyls
• 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 19/3003 : Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
• CPC Class Codes: C09K 19/3066 : in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
• CPC Class Codes: C09K 19/54 : Additives having no specific mesophase characterised by their chemical composition
• CPC Class Codes: C09K 19/586 : Optically active dopants; chiral dopants
• CPC Class Codes: C09K 2019/0444 : characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
• CPC Class Codes: C09K 2019/0448 : the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
• CPC Class Codes: C09K 2019/0466 : the linking chain being a -CF2O- chain
• CPC Class Codes: C09K 2019/122 : Ph-Ph
• CPC Class Codes: C09K 2019/123 : Ph-Ph-Ph
• CPC Class Codes: C09K 2019/3004 : Cy-Cy
• CPC Class Codes: C09K 2019/3009 : Cy-Ph
• CPC Class Codes: C09K 2019/301 : Cy-Cy-Ph
• CPC Class Codes: C09K 2019/3016 : Cy-Ph-Ph
• CPC Class Codes: C09K 2019/3027 : Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
• CPC Class Codes: C09K 2019/3422 : the heterocyclic ring being a six-membered ring
• CPC Class Codes: D01F 8/04 : from synthetic polymers
• CPC Class Codes: D01F 8/16 : with at least one other macromolecular compound obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds as constituent
• CPC Class Codes: G02F 1/13 : based on liquid crystals, e.g. single liquid crystal display cells

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.

MG¹-Z^a-Sp-Z^b-MG²  (1)

Claims

1. A compound, represented by formula (1):

MG¹-Z^a-Sp-Z^b-MG² 

 

(1)

wherein, in formula (1), MG¹ and MG² 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 —

CH₂—

may be replaced by —

O—

, —

S—

, —

CO—

or —

SiH₂—

, at least one piece of —

(CH₂)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 —

CH₂—

may be replaced by —

O—

, —

S—

, —

CO—

or —

SiH₂—

, at least one piece of —

(CH₂)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);

2. The compound according to claim 1, wherein, in formula (1), MG¹ and MG² are represented by formula (IV):



A¹-Z¹

_m

A²-Z²

_n

A³−

Z³

_q

A⁴−

Z⁴

_rRd 

 

(IV)

wherein, in formula (IV), Rd is independently —

CN, —

NCS, —

C≡

C—

CN, —

SF₅, fluorine, chlorine or straight-chain alkyl having 1 to 20 carbons, and in the Rd, at least one piece of —

CH₂—

may be replaced by —

O—

, —

S—

, —

CO—

or —

SiH₂—

, and at least one piece of —

(CH₂)₂—

may be replaced by —

CH═

CH—

or —

C≡

C—

;

A¹, A², A³ and A⁴ 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, one piece of —

CH₂—

may be replaced by —

O—

, —

S—

, —

CO—

or —

SiH₂—

, and at least one piece of —

(CH₂)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, —

CF₃, —

CHF₂, —

CH₂F, —

OCF₃, —

OCHF₂ or —

OCH₂F;

Z¹, Z², Z³ and Z⁴ are independently a single bond or alkylene having 1 to 4 carbons, and in the Z¹, the Z², the Z³ and the Z⁴, at least one piece of —

CH₂—

may be replaced by —

O—

, —

S—

, —

CO—

or —

SiH₂—

, at least one piece of —

(CH₂)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;

A¹, A², A³ and A⁴ 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, —

CF₃ or —

CHF₂; and

Z¹, Z² and Z⁴ are independently a single bond, —

(CH₂)₂—

, —

COO—

, —

OCO—

, —

CH₂O—

, —

OCH₂—

, —

CF₂O—

, —

OCF₂—

, —

CH═

CH—

, —

CF═

CF—

, —

C≡

C—

, —

CH₂CO—

, —

COCH₂—

, —

CH₂SiH₂—

, —

SiH₂CH₂—

, —

(CH₂)₂COO—

, —

OCO(CH₂)₂—

, —

(CH₂)₂CF₂O—

, —

OCF₂(CH₂)₂—

, —

(CH₂)₃O—

, —

O(CH₂)₃—

or —

(CH₂)₄—

.

4. The compound according to claim 1, wherein, in formula (1), Z^a and Z^b are independently a single bond, —

COO—

, —

OCO—

, —

CH₂O—

, —

OCH₂—

, —

CF₂O—

, —

OCF₂—

, —

CH═

CH—

, —

CF═

CF—

, —

C≡

C—

, —

CH₂CO—

, —

COCH₂—

, —

CH₂SiH₂—

or —

SiH₂CH₂—

;

in formula (sp-1), α

is straight-chain alkylene having 1 to 10 carbons, and in the α

, at least one piece of —

(CH₂)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—

, —

CH₂O—

, —

OCH₂—

, —

CF₂O—

, —

OCF₂—

, —

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), MG¹ and MG² are represented by formula (IV-1):

7. The compound according to claim 1, wherein, in formula (1), MG¹ and MG² are represented by formulas (IV-1-1-1) to (IV-1-1-55):

8. The compound according to claim 1, wherein, in formula (1), MG¹ and MG² are represented by formulas (IV-1-2-1) to (IV-1-2-30):

9. A liquid crystal composition, containing the compound according to claim 1.

10. The liquid crystal composition, containing at least two kinds of the compounds according to claim 1.

11. The liquid crystal composition according to claim 10, further containing a compound represented by formula (cp-1):

R³¹-MG³¹-Z^3a-Sp³-Z^3b-MG³²-R³² 

 

(cp-1)

wherein, R³¹ and R³² are each independently fluorine, chlorine, —

CN, —

NCS, —

SF₅ or alkyl having 1 to 20 carbons, and in the R³¹ and R³², at least one piece of —

CH₂—

may be replaced by —

O—

, —

S—

, —

CO—

or —

SiH₂—

, and at least one piece of —

(CH₂)₂—

may be replaced by —

CH═

CH—

or —

C≡

C—

;

MG³¹ and MG³² are each independently a mesogenic group;

Z^3a and Z^3b are each independently —

O—

, —

S—

, —

CO—

, —

COO—

, —

OCO—

, —

O—

CO—

O—

, —

CO—

NH—

, —

NH—

CO—

, —

CH₂CH₂—

, —

OCH₂—

, —

CH₂O—

, —

SCH₂—

, —

CH₂S—

, —

CH═

CH—

, —

CH═

CHCOO—

, —

OCO—

CH═

CH—

, —

C≡

C—

or a single bond; and

Sp³ is a straight-chain spacer group containing 4 to 40 carbons, and at least one piece of a —

CH₂ group may be replaced by —

O—

, —

S—

, —

NH—

, —

N(CH₃)—

, —

OCO—

, —

S—

CO—

, —

O—

COO—

, —

CO—

S—

, —

CO—

O—

, —

CH═

CH—

or —

C≡

C—

.

12. The liquid crystal composition according to claim 9, further containing at least one selected from an optically active compound and a polymerizable compound.

13. The liquid crystal composition according to claim 9, further containing at least one selected from an antioxidant and an ultraviolet light absorber.

14. Sheath-core conjugate fibers with an encapsulated liquid crystal, wherein the liquid crystal composition according to claim 9 is applied as a core component.

15. A fiber aggregate containing a liquid crystal, formed by uniaxially arranging the conjugate fibers with the encapsulated liquid crystal according to claim 14.

16. A fiber composite containing a liquid crystal, composed of the fiber aggregate containing the liquid crystal according to claim 15, and a binder.

17. A liquid crystal display device, including the liquid crystal composition according to claim 9.

18. The liquid crystal display device according to claim 17, wherein the device is a flexo-electric apparatus.

19. A liquid crystal display device, including the fiber composite containing the liquid crystal according to claim 16.

20. The liquid crystal display device according to claim 19, wherein the device is a flexo-electric apparatus.