Liquid crystal medium, optical device and liquid crystal compound

Patent metadata

Field	Value
Publication number	US-9611429-B2
Application number	US-201414893073-A
Country	US
Kind code	B2
Filing date	May 22, 2014
Priority date	May 27, 2013
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

A liquid crystal medium has stability to heat, light and so forth, and significantly high dielectric anisotropy, and develops an optically isotropic liquid crystal phase. Moreover, various kinds of optical devices can be used in a wide temperature range and have a short response time, a large contrast ratio and low driving voltage.
A liquid crystal composition contains achiral component T containing at least one compound 1 represented by formula (1) and a chiral agent, and develops the optically isotropic liquid crystal phase.

In formula (1), for examples, R 1 is alkyl, L 1 and L 2 are each independently fluorine or hydrogen, and X 1 is halogen.

First claim

What is claimed is:

1. A liquid crystal composition that contains achiral component T containing at least one compound 1 represented by formula (1), and a chiral agent, and develops an optically isotropic liquid crystal phase:

wherein, in formula (1), R 1 is hydrogen or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, at least one of hydrogen in the alkyl or in a group in which —CH 2 — in the alkyl is replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C— may be replaced by halogen or alkyl having 1 to 3 carbons; and
L 1 and L 2 are each independently fluorine or hydrogen, and
X 1 is halogen, —CF 3 , —OCF 3 , —C≡N or —N═C═S.

2. The liquid crystal composition according to claim 1 , wherein compound 1 is a compound represented by formula (1-1):

wherein, in formula (1-1), R 1 is hydrogen or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, at least one of hydrogen in the alkyl or in a group in which —CH 2 — in the alkyl is replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C— may be replaced by halogen or alkyl having 1 to 3 carbons; and
X 1 is halogen, —CF 3 , —OCF 3 , —C≡N or —N═C═S.

3. The liquid crystal composition according to claim 1 , wherein, in formula (1) or formula (1-1), X 1 is fluorine or —CF 3 .

4. The liquid crystal composition according to claim 1 , further containing at least one compound selected from the group of compound 3 represented by formula (3) and compound 7 represented by formula (7):

wherein, in formula (3), R 3 is hydrogen or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, —S—, —COO— or —OCO—, at least one of —CH 2 —CH 2 — in the alkyl or in a group in which at least one of —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO— may be replaced by —CH═CH—, —CF═CF— or —C≡C—, at least one of hydrogen in the alkyl, in the group in which at least one of —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO—, or in a group in which at least one of —CH 2 —CH 2 — in the group in which at least one of —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO— may be replaced by fluorine or chlorine, in which, in R 3 , neither —O— and —CH═CH— nor —CO— and —CH═CH— are adjacent;
Z 31 , Z 32 and Z 33 are each independently a single bond, alkylene having 1 to 4 carbons, and at least one of —CH 2 — in the alkylene may be replaced by —O—, —COO— or —CF 2 O—;
L 31 , L 32 , L 33 , L 34 and L 35 are each independently hydrogen or fluorine;
X 3 is hydrogen, halogen, —SF 5 or alkyl having 1 to 10 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, —S—, —COO— or —OCO—, at least one of —CH 2 —CH 2 — in the alkyl and in a group in which —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO— may be replaced by —CH═CH—, —CF═CF— or —C≡C—, at least one of hydrogen in the alkyl, in the group in which —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO—, and in a group in which at least one of —CH 2 —CH 2 — is replaced by —CH═CH— or —C≡C— may be replaced by fluorine or chlorine, in which,
in X 3 , neither —O— and —CH═CH— nor —CO— and —CH═CH— are adjacent:

wherein, in formula (7), R 7 is alkyl having 1 to 20 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, —S—, —COO— or —OCO—, at least one of —CH 2 —CH 2 — in the alkyl may be replaced by —CH═CH—, —CF═CF— or —C≡C—, at least one of hydrogen in the alkyl, in a group in which at least one of —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO—, or in a group in which at least one of —CH 2 —CH 2 — in the group in which at least one of —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO— is replaced by —CH═CH— or —C≡C— may be replaced by fluorine or chlorine, in which, in R 7 , neither —O— and —CH═CH— nor —CO— and —CH═CH— are adjacent;
L 71 , L 72 , L 73 , L 74 , L 75 , L 76 , L 77 and L 78 are each independently hydrogen or fluorine;
Z 71 , Z 72 and Z 73 are each independently a single bond, —COO— or —CF 2 O—, but at least one of Z 71 , Z 72 and Z 73 is —COO— or —CF 2 O—;
n71 and n72 are each independently 0 or 1, and satisfies an expression: n71≧n72;
in which, when both L 71 and L 72 are fluorine, Z 71 is —CF 2 O— and n71 is 1, L 74 is hydrogen,
X 7 is hydrogen, halogen, —SF 5 or alkyl having 1 to 10 carbons, at least one of —CH 2 — in the alkyl may be replaced by —O—, —S—, —COO— or —OCO—, at least one of —CH 2 —CH 2 — in the alkyl and in a group in which —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO— may be replaced by —CH═CH—, —CF═CF— or —C≡C—, at least one of hydrogen in the alkyl, in the group in which —CH 2 — in the alkyl is replaced by —O—, —S—, —COO— or —OCO—, or in the group in which at least one of —CH 2 —CH 2 — in the alkyl is replaced by —CH═CH— or —C≡C— may be replaced by fluorine or chlorine, in which, in X 7 , neither —O— and —CH═CH— nor —CO— and —CH═CH— are adjacent.

5. The liquid crystal composition according to claim 1 , containing at least one compound selected from the group represented by formulas (1) and (7) in an amount of 1 to 32% by weight based on the total weight of achiral component T.

6. The liquid crystal composition according to claim 4 , wherein compound 3 is at least one selected from the group of compounds represented by formula (3-2) and formula (3-3):

(wherein, R 3A is each independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen may be replaced by fluorine;
L 31 , L 32 , L 33 , L 34 and L 35 are each independently hydrogen or fluorine; and
X 3A is fluorine, chlorine, —CF 3 or —OCF 3 ).

7. The liquid crystal composition according to claim 4 , wherein compound 7 is at least one selected from the group of compounds represented by formulas (7-1) to (7-8):

(wherein, R 7A is hydrogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 11 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine;
L 72 , L 74 , L 75 , L 76 , L 77 and L 78 are each independently hydrogen or fluorine;
in formulas (7-1) to (7-3) and (7-6) to (7-8), Z 71 and Z 72 are each independently a single bond, —COO— or —CF 2 O—, but at least one of Z 71 and Z 72 is —COO— or —CF 2 O—, in which, in formula (7-3), when both L 71 and L 72 are fluorine, Z 71 is —CF 2 O— and n71 is 1, L 74 is hydrogen, and in formulas (7-4) and (7-5), Z 71 is each independently —COO— or —CF 2 O—, and
X 7A is fluorine, chlorine, —CF 3 or —OCF 3 ).

8. The liquid crystal composition according to claim 4 , wherein compound 7 is at least one selected from the group of compounds represented by formulas (7-2-2-E), (7-2-5-E), (7-2-2-F) and (7-2-5-F):

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• TOBATA Hitoshi
• Sago Koki
• Yamamoto Shin-Ichi
• Haseba Yasuhiro

Classifications

• C07D319/06

  not condensed with other rings · CPC title

• C09K19/586

  Optically active dopants; chiral dopants · CPC title

• C09K19/3402 Primary

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C09K19/12

  at least two benzene rings directly linked, e.g. biphenyls · CPC title

• C09K2019/122

  Ph-Ph · CPC title