Polymerizable liquid crystal composition and optically anisotropic substance having twist alignment

Patent metadata

Field	Value
Publication number	US-9505980-B2
Application number	US-201414491674-A
Country	US
Kind code	B2
Filing date	Sep 19, 2014
Priority date	Oct 31, 2013
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

A subject is to provide a polymerizable liquid crystal composition from which an optically anisotropic substance having twist alignment that is excellent in chemical strength (chemical resistance) and has only a small amount of alignment defects can be obtained. A solution is a polymerizable liquid crystal composition containing an optically active compound having a binaphthol moiety, an achiral polymerizable liquid crystal compound and a photopolymerization initiator having oxime ester.

First claim

What is claimed is:

1. A polymerizable liquid crystal composition, containing an optically active compound having a binaphthol moiety, an achiral polymerizable liquid crystal compound and a photopolymerization initiator (C) having oxime ester,
wherein an absorption maximum wavelength of a mixture including the achiral polymerizable liquid crystal compound and the optically active compound having the binaphthol moiety is in the range of 220 to 400 nanometers, and the absorption maximum wavelength is different from an absorption maximum wavelength of the photopolymerization initiator having oxime ester by 50 nanometers or more, and
wherein the achiral polymerizable liquid crystal compound is component (A) being at least one compound represented by formula (1-1), and the optically active compound having the binaphthol moiety is component (B) being at least one compound represented by formula (2-2):

wherein, in formula (1-1),
X′ is independently hydrogen, methyl, fluorine or trifluoromethyl;
W 11 is independently hydrogen or methyl;
W 12 is independently hydrogen, halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons; and
n 11 is independently an integer from 2 to 10;
in formula (2-2),
Y 2 is independently a group represented by formula (2-1);
in formula (2-1),
R 1 is independently halogen, cyano, alkenyl having 2 to 20 carbons or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the group may be replaced by —O—, excluding a case where —O— is adjacent, at least one of hydrogen in the group may be replaced by halogen, and one of hydrogen in the group may be replaced by acryloyloxy, methacryloyloxy or trifluoromethylacryloyloxy;
A 2 is independently 1,4-cyclohexylene, 1,4-phenylene, 4,4′-biphenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one of hydrogen is replaced by halogen;
Z 1 is independently a single bond, —O—, —COO—, —OCO—, —OCF 2 — or —(CH 2 ) p —, and one of —CH 2 — in —(CH 2 ) p — may be replaced by —O—;
p is independently an integer from 1 to 20; and
r is independently an integer from 1 to 3.

2. The polymerizable liquid crystal composition according to claim 1 , wherein in formula (1-1),
X 1 is independently hydrogen or methyl;
W 12 is independently hydrogen, halogen, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons;
in formula (2-2),
Y 2 is independently a group represented by formula (2-1);
in formula (2-1),
R 1 is independently alkenyl having 2 to 20 carbons or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the group may be replaced by —O—, excluding a case where —O— is adjacent, at least one of hydrogen in the group may be replaced by halogen, and one of hydrogen in the group may be replaced by acryloyloxy, methacryloyloxy or trifluoromethylacryloyloxy;
Z 1 is independently a single bond, —O—, —COO—, —OCO— or —(CH 2 ) p —, and one of —CH 2 — in —(CH 2 ) p — may be replaced by —O—; and
p is independently an integer from 1 to 10.

3. The polymerizable liquid crystal composition according to claim 1 , wherein in formula (1-1),
X 1 is independently hydrogen or methyl;
W 12 is independently hydrogen, fluorine, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons;
in formula (2-2),
Y 2 is independently a group represented by formula (2-1);
in formula (2-1),
R 1 is independently alkenyl having 2 to 20 carbons or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the group may be replaced by —O—, excluding a case where —O— is adjacent, at least one of hydrogen in the group may be replaced by halogen, and one of hydrogen in the group may be replaced by acryloyloxy, methacryloyloxy or trifluoromethylacryloyloxy;
Z 1 is independently a single bond, —O—, —COO—, —OCO— or —(CH 2 ) p —, and one of —CH 2 — in —(CH 2 ) p — may be replaced by —O—; and
p is independently an integer from 1 to 3.

4. The polymerizable liquid crystal composition according to claim 1 , further containing at least one compound represented by formula (3-1) and formula (3-2) as component (D):

wherein, in formula (3-1),
X 31 is independently hydrogen, methyl or trifluoromethyl;
Y 31 is independently alkylene having 1 to 20 carbons, and in the alkylene, at least one of hydrogen may be replaced by fluorine or chlorine, and at least one of —CH 2 — may be replaced by —O—, —S—, —COO—, —OCO—, —OCOO—, —CH═CH— or —C≡C—;
W 31 is independently hydrogen, fluorine, chlorine, methyl or ethyl, and at least one of hydrogen in the methyl and the ethyl may be replaced by halogen;
W 32 is independently hydrogen, halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons;
in formula (3-2),
W 31 is independently hydrogen, fluorine, chlorine, methyl or ethyl, and at least one of hydrogen in the methyl and the ethyl may be replaced by halogen;
W 32 is independently hydrogen, halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons;
X 32 is independently hydrogen, methyl or trifluoromethyl; and
Y 32 is independently alkylene having 1 to 20 carbons, and in the alkylene, at least one of hydrogen may be replaced by fluorine or chlorine, and at least one of —CH 2 — may be replaced by —O—, —S—, —COO—, —OCO—, —OCOO—, —CH═CH— or —C≡C—.

5. The polymerizable liquid crystal composition according to claim 1 , further containing at least one compound represented by formula (4) as component (E):

wherein, in formula (4),
X 4 is independently hydrogen, methyl, fluorine or trifluoromethyl;
W 42 is independently hydrogen, halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons, and in the alkyl and the alkoxy, at least one of hydrogen may be replaced by fluorine;
W 41 is independently halogen, nitro, cyano, phenyl, benzyl, alkyl having 1 to 7 carbons, alkoxy having 1 to 7 carbons, alkoxycarbonyl (—COOR a ; R a is straight-chain alkyl having 1 to 7 carbons) or alkylcarbonyl (—COR b ; R b is straight-chain alkyl having 1 to 16 carbons), and in the alkyl and the alkoxy, at least one of hydrogen may be replaced by fluorine;
s is an integer from 0 to 4;
n 41 is independently an integer from 2 to 10;
n 42 is an integer from 1 to 3;
Z 41 is independently a single bond, —O—, —CO—, —CH═CH—, —COO—, —COO—, —OCO—CH═CH—COO— or —OCOO—; and
Z 42 is independently a single bond, —CH 2 CH 2 — or —CH═CH—.

6. The polymerizable liquid crystal composition according to claim 1 , further containing at least one compound represented by formula (5) as component (F):

wherein, in formula (5),
X 51 is hydrogen, methyl or trifluoromethyl;
R 5 is cyano, trifluoromethoxy, alkyl having 1 to 20 carbons, alkyl ester having 1 to 20 carbons (—COOR c , —OCOR c or —CH═CH—COORS; R c is straight-chain alkyl having 1 to 20 carbons) or alkoxy having 1 to 20 carbons, and in the alkyl and the alkoxy, at least one of hydrogen may be replaced by fluorine;
ring A 51 is 1,4-phenylene or 1,4-cyclohexylene;
W 51 and W 52 are independently hydrogen, halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons, and in the alkyl and the alkoxy, at least one of hydrogen may be replaced by fluorine;
Z 51 is a single bond, —O—,

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Hirai Yoshiharu
• Miyagawa Nagahisa
• Ootsuki Daisuke

Classifications

• C09K19/322 Primary

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

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K19/54

  Additives having no specific mesophase {characterised by their chemical composition} · CPC title

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title