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

Patent metadata

Field	Value
Publication number	US-11299675-B2
Application number	US-201816650852-A
Country	US
Kind code	B2
Filing date	Jul 13, 2018
Priority date	Sep 26, 2017
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

Abstract

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 the compound is used in a liquid crystal display device; and a composition containing the compound. The compound is represented by formula (1). In formula (1), for example, P1 is a group represented by any one of formulas (1b) to (1i), P2 is a group represented by formula (1d), Sp1 and Sp2 are a single bond, Z1, Z2, Z3, Z4 and Z5 are —COO—, and ring A1, ring A2, ring A3 and ring A4 are 1,4-phenylene:

First claim

What is claimed is:

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

wherein, in formula (1),
a and b are independently 0, 1 or 2, wherein 0≤a+b≤3,
ring A 1 , ring A 2 , ring A 3 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, and when a is 2, two of ring A 1 may be different, and when b is 2, two of ring A 4 may be different;
Z 1 , Z 2 , Z 3 , Z 4 and Z 5 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—, —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, in which at least one in Z 2 , Z 3 or Z 4 is —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, and when a is 2, two Z*s may be different, and two Z 5 s may be different;
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—, —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;
P 1 is a group represented by any one of formulas (1b) to (1i); and
P 2 is a group represented by formula (1d);

wherein, in formulas (1b) to (1i),
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, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one —CH 2 — may be replaced by —O—; and
R 3 , R 4 and R 5 are independently hydrogen or 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.

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

wherein, in formula (1),
a and b are independently 0, 1 or 2, wherein 0≤a+b≤2;
ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohex enylene, 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, and when a is 2, two of ring A 1 may be different, and when b is 2, two of ring A 4 may be different;
Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently a single bond, —(CH 2 ) 2 —, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CF═CF—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, in which at least one in Z 2 , Z 3 or Z 4 is —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, and when a is 2, two Z's may be different, and two Z 5 s may be different;
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; and
P 1 is a group represented by any one of formulas (1b) to (1i), and P 2 is a group represented by formula (1d);

wherein, in formulas (1b) to (1i),
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, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one —CH 2 — may be replaced by —O—; and
R 3 , R 4 and R 5 are independently hydrogen or 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.

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

wherein, in formulas (1-1) to (1-3),
R 5 is hydrogen or 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 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl or anthracene-2,6-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 2 , Z 3 and Z 4 are independently a single bond, —(CH 2 ) 2 —, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CF═CF—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, in which at least one in Z 2 , Z 3 and Z 4 is —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCHCH—;
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—, —OCOO— 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; and
P 1 is a group represented by any one of formulas (1b) to (1i);

wherein
M1 and M2 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, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one —CH 2 — may be replaced by —O—; and
R 3 , R 4 and R 5 are independently hydrogen or straight-chain, branched-chain or cycl

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Yano Tomohiro
• Kondo Fumitaka
• SAGO Hiroki

Classifications

• C09K19/12

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

• C07C69/94

  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 title

• C09K19/56

  Aligning agents · CPC title

• C09K19/2028

  containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3 · CPC title

• C09K2019/2035

  Ph-COO-Ph · CPC title