Liquid crystal composition, method for manufacturing the same, and film

Patent metadata

Field	Value
Publication number	US-9464228-B2
Application number	US-201514661771-A
Country	US
Kind code	B2
Filing date	Mar 18, 2015
Priority date	Sep 25, 2012
Publication date	Oct 11, 2016
Grant date	Oct 11, 2016

Abstract

A method for manufacturing a liquid crystal composition, the method including concurrently obtaining a liquid crystal compound represented by the formula (I) and a liquid crystal compound represented by the formula (II), by allowing a compound represented by the formula (III) to react with a carboxylic acid represented by the formula (IV) and a carboxylic acid represented by the formula (V), wherein P 1 represents a polymerizable group; Sp 1 represents a C 3-12 divalent aliphatic group, etc; T 1 represents a 1,4-phenylene group; T 2 represents a divalent group having a single bond or cyclic structure; A 1 represents —COO—, etc; A 2 and A 3 represents —OCO—, etc; X represents a hydrogen atom, C 1-12 alkyl group, etc; Y 1 and Y 2 represents O, NR 1 or S; R 1 represents a hydrogen atom or methyl group; Formula (I) P 1 -Sp 1 -T 1 -A 1 -B-A 2 -T 1 -Sp 1 -P 1 ; Formula (II) P 1 -Sp 1 -T 1 -A 1 -B-A 3 -T 2 -X; Formula (III) being HY 1 —B—Y 2 H; Formula (IV) P 1 -Sp 1 -T 1 -COOH; Formula (V) X-T 2 -COOH.

First claim

What is claimed is:

1. A method for manufacturing a liquid crystal composition, the method comprising concurrently obtaining a liquid crystal compound represented by the formula (I) below and a liquid crystal compound represented by the formula (II) below, by allowing a compound represented by the formula (III) below to react with a carboxylic acid represented by the formula (IV) below and a carboxylic acid represented by the formula (V) below;
P 1 -Sp 1 -T 1 -A 1 -B-A 2 -T 1 -Sp 1 -P 1   Formula (I)

P 1 -Sp 1 -T 1 -A 1 -B-A 3 -T 2 -X   Formula (II)

HY 1 —B—Y 2 H   Formula (III)

P 1 -Sp 1 -T 1 -COOH   Formula (IV)

X-T 2 -COOH   Formula (V)

wherein,
P 1 represents a polymerizable group;
Sp 1 represents a C 3-12 divalent aliphatic group which may have a substituent, and one CH 2 or two or more non-adjacent (CH 2 )s in the aliphatic group may be substituted by —O—, —S—, —OCO—, —COO— or —OCOO—;
T 1 represents a 1,4-phenylene group;
T 2 represents a divalent group having a single bond or cyclic structure;
A 1 represents —COO—, —CONR 1 — or —COS—, wherein R 1 represents a hydrogen atom or methyl group;
each of A 2 and A 3 independently represents —OCO—, —NR 1 CO— or —SCO—; wherein R 1 represents a hydrogen atom or methyl group;
B represents a divalent group having a cyclic structure which may have a substituent;
X represents a hydrogen atom, branched or straight-chain C 1-12 alkyl group, branched or straight-chain C 1-12 alkoxy group, phenyl group, cyano group, halogen atom, nitro group, acetyl group, vinyl group, formyl group, —OC(═O)R, wherein R represents a C 1-12 alkyl group, N-acetylamide group, acryloylamino group, N,N-dimethylamino group, N-maleimide group, methacryloylamino group, aryloxy group, N-alkyloxycarbamoyl group having a C 1-4 alkyl group, allyloxycarbamoyl group, N-(2-methacryloyloxyethyl)carbamoyloxy group, N-(2-acryloyloxyethyl)carbamoyloxy group or a structure represented by the Formula (V-I) below;
each of Y 1 and Y 2 independently represents O, NR 1 , wherein R 1 represents a hydrogen atom or methyl group, or S;
-A 4 -T 4 -Sp 2 -P 2   Formula (V-I)

wherein, P 2 represents a polymerizable group or hydrogen atom, and each of A 4 , T 4 and Sp 2 are independently the same as A 2 , T 2 and Sp 1 .

2. The method for manufacturing a liquid crystal composition of claim 1 , wherein in the formulae (I) to (V), X represents a hydrogen atom, branched or straight-chain C 1-12 alkyl group, branched or straight-chain C 1-12 alkoxy group, phenyl group, cyano group, halogen atom, nitro group, acetyl group or vinyl group.

3. The method for manufacturing a liquid crystal composition of claim 1 , further comprising;
activating the carboxylic acid represented by the formula (IV) and the carboxylic acid represented by the formula (V), by converting the carboxylic acids into a mixed acid anhydride or acid halide, wherein
subsequent to the activating, the compound represented by the formula (III) is allowed to react with the activated carboxylic acid represented by the formula (IV) and the activated carboxylic acid represented by the formula (V), in the presence of a base.

4. The method for manufacturing a liquid crystal composition of claim 1 ,
wherein feed ratio by mole of the carboxylic acid represented by the formula (IV) and the carboxylic acid represented by the formula (V) falls in the range from 75:25 to 99:1.

5. The method for manufacturing a liquid crystal composition of claim 1 ,
wherein production ratio by mole of the compound represented by the formula (I) and the compound represented by the formula (II) falls in the range from 50:50 to 98:2.

6. The method for manufacturing a liquid crystal composition of claim 1 ,
wherein compositional ratio by mass of the compound represented by the formula (I) and the compound represented by the formula (II), in the liquid crystal composition, falls in the range from 50:50 to 95:5.

7. The method for manufacturing a liquid crystal composition of claim 1 , wherein B represents any one linking group selected from the group (VI) consisting of the linking groups below;

wherein, each of R 2 to R 10 independently represents a hydrogen atom, branched or straight-chain C 1-4 alkyl group, branched or straight-chain C 1-4 alkoxy group, halogen atom, or, C 1-3 alkoxycarbonyl group.

8. The method for manufacturing a liquid crystal composition of claim 1 , wherein T 2 represents any one linking group selected from the group (VII) consisting of the linking groups below;

9. The method for manufacturing a liquid crystal composition of claim 1 , wherein B represents any one linking group selected from the group (VIII) consisting of the linking groups below;

wherein Me is methyl group.

10. The method for manufacturing a liquid crystal composition of claim 1 , wherein X represents a branched or straight-chain C 1-4 alkyl group, straight-chain C 1 or C 2 alkoxy group, or, phenyl group.

11. The method for manufacturing a liquid crystal composition of claim 1 , wherein
each of Y 1 and Y 2 represents O,
A 1 represents —COO—, and
each of A 2 and A 3 represents —OCO—.

Assignees

• Fujifilm Corp

Inventors

• Katoh Shunya
• Matsuyama Hiroshi
• Yoshikawa Masaru

Classifications

• C09K2019/044

  the specific unit being a perfluoro chain used as an end group · CPC title

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• C09K19/54 Primary

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

• C09K19/2007 Primary

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

• C09K19/3444

  the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine · CPC title