Polymerizable polar compound, liquid crystal composition and liquid crystal display element

Patent metadata

Field	Value
Publication number	US-10759998-B2
Application number	US-201816215655-A
Country	US
Kind code	B2
Filing date	Dec 11, 2018
Priority date	Jun 26, 2018
Publication date	Sep 1, 2020
Grant date	Sep 1, 2020

Abstract

To provide a polar compound having high chemical stability, a high ability to align liquid crystal molecules, and high solubility in a liquid crystal composition, and a high voltage holding ratio of a liquid crystal display element.
A compound represented by Formula (1):

R 1 is a hydrogen atom or an alkyl group that may be substituted; a is 2 to 12; and R 2 is Formula (1-a), Formula (1-b), and Formula (1-c);

Sp 1 to Sp 3 are a single bond or an alkylene group that may be substituted; M 1 and M 2 are H, F, Cl, or an alkyl group that may be substituted; and X 1 is —OH, —NH 2 , —OR 3 , —N(R 3 ) 2 , —COOH, —SH or —Si(R 3 ) 3 .

First claim

What is claimed is:

1. A compound represented by Formula (1):

in Formula (1),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O— or —S—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by R 1 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
a is an integer of 2 to 12;
M 1 and M 2 are independently a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted with a fluorine atom or a chlorine atom; and
R 2 is a group selected from among groups represented by Formula (1-a), Formula (1-b), and Formula (1-c);

in Formula (1-a), Formula (1-b), and Formula (1-c),
Sp 2 and Sp 3 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 2 and Sp 3 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
R 3 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, or an alkoxyalkyl group having 1 to 9 carbon atoms;
X 1 is independently —OH, —NH 2 , —N(R 4 ) 2 , —COOH, —SH, or —Si(R 4 ) 3 ;
in —N(R 4 ) 2 , and —Si(R 4 ) 3 ,
R 4 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by R 4 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom,
in Formula (1),
Sp 1 is a single bond or an alkylene group having 1 to 15 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 1 , at least one hydrogen atom is optionally substituted with a fluorine atom, a chlorine atom, or a group represented by Formula (1-d);

in Formula (1-d),
Sp 4 is a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 4 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
M 3 and M 4 are independently a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted with a fluorine atom or a chlorine atom; and
R 5 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and at least one hydrogen atom is optionally substituted with a fluorine atom or a chlorine atom.

2. The compound according to claim 1 , wherein, in Formula (1), R 2 is a group represented by Formula (1-a) or Formula (1-b).

3. The compound according to claim 1 , wherein, in Formula (1), R 2 is a group represented by Formula (1-a) or Formula (1-b), and in Formula (1-a) and Formula (1-b), X 1 is independently —OH, —NH 2 , —COOH, or —SH.

4. The compound according to claim 1 , which is represented by any one of Formula (1-1) to Formula (1-6):

in Formula (1-1) to Formula (1-6),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by R 1 , at least one hydrogen atom is optionally substituted with a fluorine atom;
a is an integer of 2 to 8;
Sp 1 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 1 , Sp 2 , Sp 3 , and Sp 4 , at least one hydrogen atom is optionally substituted with a fluorine atom;
Sp 5 and Sp 6 are independently a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 5 and Sp 6 , at least one hydrogen atom is optionally substituted with a fluorine atom;
R 3 is a hydrogen, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxyalkyl group having 1 to 6 carbon atoms;
R 5 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

5. The compound according to claim 1 , which is represented by any one of Formula (1-7) to Formula (1-24):

in Formula (1-7) to Formula (1-24),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—;
a is an integer of 2 to 8;
Sp 1 is a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—; and
R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

6. The compound according to claim 1 , which is represented by any one of Formula (1-25) to Formula (1-48):

in Formula (1-25) to Formula (1-48),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—;
Sp 1 is a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—.

7. The compound according to claim 1 , which is represented by any one of Formula (1-49) to Formula (1-56):

in Formula (1-49) to Formula (1-56),
R 1 i

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Tanaka Hiroyuki

Classifications

• C09K19/3001 Primary

  Cyclohexane rings · CPC title

• G02F1/13712

  the liquid crystal having negative dielectric anisotropy · CPC title

• G02F1/13706

  the liquid crystal having positive dielectric anisotropy · CPC title

• G02F1/13775

  Polymer-stabilized liquid crystal layers · CPC title

• C09K2019/3009

  Cy-Ph · CPC title