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

Patent metadata

Field	Value
Publication number	US-2019292463-A1
Application number	US-201716306578-A
Country	US
Kind code	A1
Filing date	May 31, 2017
Priority date	Jun 3, 2016
Publication date	Sep 26, 2019
Grant date	—

Abstract

wherein, Sp4 and Sp5 are a single bond or alkylene having 1 to 10 carbons; S1 is >CH—, and S2 is >C<; and X is —OH.

First claim

1 . A compound, represented by formula (1):
R 1 -MES-Sp 1 -P 1   (1)
wherein, in formula (1),
R 1 is alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —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 piece of —CH 2 — may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, 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, and in the groups, at least one hydrogen is replaced by a group selected from groups represented by formula (1a), formula (1b), formula (1c) and formula (1 d);

wherein, in formula (1a), formula (1b), formula (1c) and formula (1d),
Sp 2 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, 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;
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;
R 2 is hydrogen or alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —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; and

in formula (1),
P 1 is a group selected from groups represented by formula (1e) and formula (1f);

wherein, in formula (1e) and (1f),
Sp 3 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, 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;
M 3 and M 4 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;
X 1 is —OH, —NH 2 , —OR 5 , —N(R 5 ) 2 , —COOH, —SH, —B(OH) 2 or —Si(R 5 ) 3 ; and
R 3 is a group selected from groups represented by formula (1g), formula (1h) and formula (1i);

wherein, in formula (1g), formula (1h) and formula (1i),
Sp 4 and Sp 5 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, 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;
S 1 is >CH— or >N—;
S 2 is >C< or >Si<;
X 1 is —OH, —NH 2 , —OR 5 , —N(R 5 ) 2 , —COOH, —SH, —B(OH) 2 or —Si(R 5 ) 3 ; and

in —OR 5 , —N(R 5 ) 2 and —Si(R 5 ) 3 ,
R 5 is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one piece of —CH 2 — may be replaced by —O—, and at least one piece of —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by halogen.

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

wherein, in formula (1-1),
R 1 is alkyl having 1 to 12 carbons, and in the alkyl, at least one piece of —CH 2 — may be replaced by —O—, 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 fluorine;
ring A 1 and ring A 2 are independently 1,4-cycloxylene, 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;
a is 0, 1, 2, 3 or 4;
Z 1 is a single bond or alkylene having 1 to 6 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, 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 fluorine or chlorine;
Sp 1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, 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 fluorine or chlorine, and in the groups, at least one hydrogen is replaced by a polymerizable group represented by formula (1a);

wherein, in formula (1a),
Sp 2 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, 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;
M 1 and M 2 are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine;
R 2 is hydrogen or alkylene having 1 to 15 carbons, and in the alkylene, at least one piece of —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 fluorine or chlorine; and

in formula (1-1),
P 1 is a group selected from groups represented by formula (1e) and formula (1f);

wherein, in formula (1e) and formula (1f),
Sp 3 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, 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 fluorine or chlorine;
M 3 and M 4 are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine;
X 1 is —OH, —NH 2 , —OR 5 , —N(R 5 ) 2 , —COOH, —SH or —Si(R 5 ) 3 ; and
R 3 is a group selected from groups represented by formula (1g) and formula (1h);

wherein, in formula (1g) and formula (1h),
Sp 4 and Sp 5 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH 2 — may be replaced by —O—, —NH—, —CO—, —COO—, —OCO—

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Yano Masakazu
• Kondou Fumitaka
• Ogita Kazuhiro

Classifications

• C09K2019/122

  Ph-Ph · CPC title

• C09K19/3003

  Compounds containing at least two rings in which the different rings are directly linked (covalent bond) · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K2019/3425

  Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title

• C09K2019/308

  Cy-Cy-COO-Ph-Ph · CPC title