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

Patent metadata

Field	Value
Publication number	US-10494571-B2
Application number	US-201715795272-A
Country	US
Kind code	B2
Filing date	Oct 27, 2017
Priority date	Oct 28, 2016
Publication date	Dec 3, 2019
Grant date	Dec 3, 2019

Abstract

In Formula (1), for example, W1 is an alkoxycarbonyl group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, or a polymerizable functional group, A1 is independently 1,4-phenylene or naphthalene-2,6-diyl, Z1 is a linking group, m and n are independently an integer of 0 to 7, and satisfy 3≤m+n≤8, and P1 is a polymerizable functional group.

First claim

What is claimed is:

1. A polymerizable liquid crystal composition containing a compound represented by Formula (1),

in Formula (1),
W 1 is an alkoxycarbonyl group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms or a group represented by Formula (2), and at least one —CH 2 — in the alkoxycarbonyl may be replaced with —O—,
A 1 is independently 1,4-phenylene or naphthalene-2,6-diyl, and at least one hydrogen of the 1,4-phenylene and the naphthalene-2,6-diyl may be replaced with fluorine, chlorine, trifluoromethyl, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having 1 to 5 carbon atoms, or an alkanoyl group having 1 to 5 carbon atoms,
Z 1 is independently —CH 2 CH 2 —, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —OCH 2 CH 2 O—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —OCOCH 2 CH 2 —, —CH 2 CH 2 OCO—, or —COOCH 2 CH 2 —,
m and n are independently an integer of 0 to 7, and satisfy 3≤m+n≤8, and
P 1 is independently a group represented by Formula (2),

in Formula (2),
Y 1 is a single bond, —O—, —COO—, —OCO—, or —OCOO—,
Q 1 is a single bond or an alkylene group having 1 to 20 carbon atoms, and at least one —CH 2 — in the alkylene may be replaced with —O—, —COO—, or —OCO—, and
PG is a functional group represented by any one of Formula (PG-1) to Formula (PG-9),

in Formula (PG-1) to Formula (PG-9),
R 1 is independently hydrogen, halogen, methyl, ethyl, or trifluoromethyl.

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

3. The polymerizable liquid crystal composition according to claim 1 ,
wherein, in Formula (2), PG is a functional group represented by Formula (PG-1).

4. The polymerizable liquid crystal composition according to claim 1 ,
wherein Z 1 is independently —COO—, —OCO—, —CH 2 CH 2 COO—, or —OCOCH 2 CH 2 —, and at least one of Z 1 is —CH 2 CH 2 COO— or —OCOCH 2 CH 2 —.

5. The polymerizable liquid crystal composition according to claim 1 ,
wherein the compound represented by Formula (1) is contained in an amount of 1 to 50% by weight based on a total weight of the polymerizable liquid crystal composition.

6. The polymerizable liquid crystal composition according to claim 1 , further containing a compound represented by Formula (M1),

in Formula (M1),
A M is independently 1,4-phenylene, 1,4-cyclohexylene, or naphthalene-2,6-diyl, and at least one hydrogen in the 1,4-phenylene or the naphthalene-2,6-diyl may be replaced with fluorine, chlorine, cyano, formyl, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxycarbonyl group having 1 to 5 carbon atoms, an alkanoyl group having 1 to 5 carbon atoms, or a fluoroalkyl group having 1 to 5 carbon atoms,
Z M is independently a single bond, —CH 2 CH 2 —, —COO—, —OCO—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —OCOCH 2 CH 2 —, —CH 2 CH 2 OCO— or —COOCH 2 CH 2 —,
r and s are independently an integer of 1 to 3,
W M is independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a fluoroalkyl group having 1 to 10 carbon atoms,
Y M is independently a single bond, —O—, —COO—, —OCO—, or —OCOO—,
Q M is independently a single bond or an alkylene group having 1 to 20 carbon atoms, and at least one —CH 2 — in the alkylene may be replaced with —O—, —COO—, or —OCO—, and
PG M is independently a functional group represented by any one of Formula (PG-1) to Formula (PG-9),

in Formula (PG-1) to Formula (PG-9), R 1 is independently hydrogen, halogen, methyl, ethyl, or trifluoromethyl.

7. The polymerizable liquid crystal composition according to claim 6 ,
wherein the compound represented by Formula (1) is contained in an amount of 10 to 90% by weight based on a total weight of the compound represented by Formula (1) and the compound represented by Formula (M1).

8. The polymerizable liquid crystal composition according to claim 6 ,
wherein in Formula (M1), PG M is a functional group represented by Formula (PG-1).

9. A liquid crystal polymerized film obtained by polymerizing the polymerizable liquid crystal composition according to claim 1 .

10. The liquid crystal polymerized film according to claim 9 ,
wherein liquid crystal molecules are fixed in a state where the liquid crystal molecules are aligned by the photoalignment film.

11. A retardation film composed of the liquid crystal polymerized film according to claim 9 .

12. A polarizing plate having the liquid crystal polymerized film according to claim 9 .

13. A display device having the liquid crystal polymerized film according to claim 9 .

14. A polymerizable liquid crystal compound represented by Formula (1-1),

in Formula (1-1),
T 1 is an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms,
A 1 is independently 1,4-phenylene, and at least one hydrogen in the 1,4-phenylene may be replaced with fluorine, chlorine, trifluoromethyl, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having 1 to 5 carbon atoms, or an alkanoyl group having 1 to 5 carbon atoms,
Z 1 is independently —COO—, —OCO—, —CH 2 CH 2 COO—, or —OCOCH 2 CH 2 —,
m and n each are 2 or 3,
Y 1 is a single bond, —O—, —COO—, —OCO—, or —OCOO—,
Q 1 is a single bond or an alkylene group having 1 to 20 carbon atoms, and at least one —CH 2 — in the alkylene may be replaced with —O—, —COO—, or —OCO—, and
PG is a functional group represented by any one of Formula (PG-1) to Formula (PG-9),

in Formula (PG-1) to Formula (PG-9), R 1 is independently hydrogen, halogen, methyl, ethyl, or trifluoromethyl.

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Ootsuki Daisuke
• Miyagawa Nagahisa

Classifications

• C09K19/32

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

• C09K19/3852

  Poly(meth)acrylate derivatives · CPC title

• C09K19/3809 Primary

  Polyesters; Polyester derivatives, e.g. polyamides · CPC title

• C09K19/2007 Primary

  the chain containing -COO- or -OCO- groups · 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