Polymerizable liquid crystal compound, polymerizable liquid crystal composition and liquid crystal polymerized film

Patent metadata

Field	Value
Publication number	US-10844283-B2
Application number	US-201815896019-A
Country	US
Kind code	B2
Filing date	Feb 13, 2018
Priority date	Feb 17, 2017
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

A polymerizable liquid crystal compound represented by formula (1). In formula (1), A 1 is 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, pyridine-2,5-diyl, 1,3-dioxane-2,5-diyl or naphthalene-2,6-diyl, Z 1 is a connecting group, m and n are independently an integer from 0 to 5, in which an expression: 1≤m+n≤8 holds, X 1 is alkylene having 1 to 5 carbons, in which an atom thereof may be replaced by a hetero atom, and at least one of R 1 is a polymerizable functional group.

First claim

What is claimed is:

1. A polymerizable liquid crystal compound, represented by formula (1):

wherein, in formula (1),
A 1 is independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, pyridine-2,5-diyl, 1,3-dioxane-2,5-diyl or naphthalene-2,6-diyl, and in the 1,4-phenylene or naphthalene-2,6-diyl, at least one hydrogen may be replaced by fluorine, chlorine, trifluoromethyl, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 10 carbons, alkoxycarbonyl having 1 to 10 carbons, alkylester having 1 to 10 carbons, alkanoyl having 1 to 10 carbons or a polymerizable functional group,
Z 1 is independently a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —OCH 2 CH 2 O—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —OCOCH 2 CH 2 —, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —CH═CH—, —N═C(CH 3 )—, —C(CH 3 )═N—, —N═N—, —C═C— or —CH═N—N═CH—,
m and n are independently an integer from 0 to 5, in which an expression: 1≤m+n≤8 holds,
X 1 is alkylene having 1 to 5 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —CO—, —S—, —O— or —NH—, and at least one —CH 2 —CH 2 — may be replaced by —CH═CH—,
at least one hydrogen in —CH 2 —, —CH═ or —NH— described above may be replaced by fluorine, chlorine, trifluoromethyl, alkyl having 1 to 10 carbons or alkanoyl having 1 to 10 carbons,
one of R 1 is a polymerizable functional group, and
the other of R 1 is a polymerizable functional group, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, cyano, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkylester having 1 to 12 carbons or alkoxycarbonyl having 1 to 12 carbons.

2. The polymerizable liquid crystal compound according to claim 1 , wherein the polymerizable functional group is independently represented by formula (2):

wherein, in formula (2),
Y 1 is a single bond, —O—, —COO—, —OCO— or —OCOO—, and
Q 1 is a single bond or alkylene having 1 to 20 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —COO— or —OCO—, and PG is a polymerizable group represented by any one of formula (PG-1) to formula (PG-9):

wherein, in formula (PG-1) to formula (PG-9), R 3 is each independently hydrogen, fluorine, methyl, ethyl or trifluoromethyl.

3. The polymerizable liquid crystal compound according to claim 1 , wherein Z 1 is independently a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CH 2 CH 2 —, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO— or —OCOCH 2 CH 2 —.

4. The polymerizable liquid crystal compound according to claim 2 , wherein both of R 1 are a group represented by formula (2).

5. The polymerizable liquid crystal compound according to claim 1 , wherein X 1 is alkylene having 2 to 4 carbons, and in the alkylene, —CH 2 — may be replaced by —CO—, —S—, —O— or —NH—, and at least one hydrogen may be replaced by fluorine, chlorine, trifluoromethyl, alkyl having 1 to 5 carbons or alkanoyl having 1 to 5 carbons.

6. The polymerizable liquid crystal compound according to claim 2 , wherein both of R 1 are a group represented by formula (2), and PG is a polymerizable group represented by formula (PG-1).

7. The polymerizable liquid crystal compound according to claim 1 , wherein m and n are independently 1, 2 or 3.

8. A polymerizable liquid crystal composition, containing the polymerizable liquid crystal compound according to claim 1 .

9. A polymerizable liquid crystal composition, containing 10 to 100% by weight of the polymerizable liquid crystal compound according to claim 1 based on the total weight of the polymerizable liquid crystal compound.

10. A liquid crystal polymerized film, wherein the polymerizable liquid crystal composition according to claim 8 is polymerized.

11. A liquid crystal polymerized film comprising a substrate-embedded liquid crystal polymer, and the liquid crystal polymerized film having an alignment film on a substrate, wherein a polymerizable liquid crystal compound in the polymerizable liquid crystal composition according to claim 8 is aligned by the alignment film and polymerized.

12. The liquid crystal polymerized film according to claim 11 , wherein the polymerizable liquid crystal compound in the polymerizable liquid crystal composition is immobilized in a state of homogeneous alignment.

13. A phase difference film comprising the liquid crystal polymerized film according to claim 10 .

14. A polarizing plate having the liquid crystal polymerized film according to claim 10 .

15. A display device having the liquid crystal polymerized film according to claim 10 .

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Ootsuki Daisuke

Classifications

• C07C69/757 Primary

  having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety · CPC title

• C07C69/78

  Benzoic acid esters · CPC title

• C09K2019/0448

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

• C08F22/20

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• C08F122/1006

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title