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

Patent metadata

Field	Value
Publication number	US-10392339-B2
Application number	US-201615541038-A
Country	US
Kind code	B2
Filing date	Feb 4, 2016
Priority date	Feb 9, 2015
Publication date	Aug 27, 2019
Grant date	Aug 27, 2019

Abstract

Provided is a polar compound having high chemical stability, high capability of aligning liquid crystal molecules, high solubility in a liquid crystal composition, and a large voltage holding ratio when used in a liquid crystal display device. The compound is represented by formula (1):

in which, for example, R 1 is alkyl having 1 to 15 carbons; MES is a mesogen group having at least one ring; Sp 1 is a single bond or alkylene having 1 to 10 carbons; M 1 and M 2 are hydrogen; and R 2 is a group represented by formulas (1a) to (1c):

in which, Sp 2 and Sp 3 are a single bond or alkylene having 1 to 10 carbons; S 1 is >CH—; S 2 is >C<; and X 1 is —OH.

First claim

What is claimed is:

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

wherein, in formula (1),
R 1 is alkyl having 1 to 15 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C, and in the groups, at least one hydrogen may be replaced by halogen;
MES is a mesogen group having at least one ring;
Sp 1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, and at least one (CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen;
M 1 and M 2 are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen; and
R 2 is a group represented by formula (1a), formula (1b) or formula (1c):

wherein, in formula (1a), formula (1b) and formula (1c),
Sp 2 and Sp 3 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C— and in the groups, at least one hydrogen may be replaced by halogen;
S 1 is >CH— or >N—;
S 2 is >C< or >Si<; and
X 1 is a group represented by —OH, —NH 2 , —OR 3 , —N(R 3 ) 2 , formula (x1), —COOH, —SH, —B(OH) 2 or —Si(R 3 ) 3 , in which R 3 is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one CH 2 — may be replaced by —O—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by halogen, and w in formula (x1) is 1, 2, 3 or 4:

2. The compound according to claim 1 , represented by formula (1-1):

wherein, in formula (1-1),
R 1 is alkyl having 1 to 15 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C, and in the groups, at least one hydrogen may be replaced by halogen;
ring A 1 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine;
Z 1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen;
Sp 1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C— and in the groups, at least one hydrogen may be replaced by halogen;
M 1 and M 2 are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen;
a is 0, 1, 2, 3 or 4; and
R 2 is a group represented by formula (1a) or formula (1b):

wherein, in formula (1a) and formula (1b),
Sp 2 and Sp 3 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C— and in the groups, at least one hydrogen may be replaced by halogen;
S 1 is >CH— or >N—; and
X 1 is a group represented by —OH, —NH 2 , —OR 3 , —N(R 3 ) 2 , formula (x1), —COOH, —SH, —B(OH) 2 or —Si(R 3 ) 3 , in which R 3 is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one CH 2 — may be replaced by —O—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by halogen, and w in formula (x1) is 1, 2, 3 or 4:

3. The compound according to claim 1 , represented by formula (1-2):

wherein, in formula (1-2),
R 1 is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 1 to 14 carbons or alkenyloxy having 2 to 14 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine;
ring A 1 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine;
Z 1 is a single bond, —(CH 2 ) 2 —, —CH═CH—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 — or —CF═CF—;
Sp 1 and Sp 2 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —COO— or —OCO—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine;
M 1 and M 2 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
X 1 is a group represented by —OH, —NH 2 , —OR 3 , —N(R 3 ) 2 , formula (x1), —COOH, —SH, —B(OH) 2 or —Si(R 3 ) 3 , in which R 3 is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine, and w in formula (x1) is 1, 2, 3 or 4; and

wherein, a is 0, 1, 2, 3 or 4.

4. The compound according to claim 1 , represented by any one of formula (1-3) to formula (1-6):

wherein, in formula (1-3) to formula (1-6),
R 1 is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 1 to 14 carbons or alkenyloxy having 2 to 14 carbons, and in the groups, at least one hydrogen may be repla

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Tanaka Hiroyuki
• Yano Masakazu
• Kondou Fumitaka
• Ogita Kazuhiro

Classifications

• C09K2019/3077

  Cy-Cy-COO-Ph · CPC title

• C09K2019/3015

  Cy-Cy-Ph-Cy · CPC title

• C09K2019/3006

  Cy-Cy-Cy · CPC title

• C09K2019/181

  Ph-C≡C-Ph · CPC title

• C09K2019/0444

  characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group · CPC title