Composition, optical film including composition, and method of producing optical film

Patent metadata

Field	Value
Publication number	US-10557978-B2
Application number	US-201615215754-A
Country	US
Kind code	B2
Filing date	Jul 21, 2016
Priority date	Jul 24, 2015
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

Abstract

The present invention provides, as a composition containing a smectic liquid crystal compound which can be used for production of a homogeneous optical film at a temperature around room temperature, a composition containing a smectic liquid crystal compound having a 1,4-cyclohexyl group, which smectic liquid crystal compound having the 1,4-cyclohexyl group contains (i) 100 parts by mass of a smectic liquid crystal compound having a trans-1,4-cyclohexyl group and (ii) 0.1 parts by mass to 10 parts by mass of a smectic liquid crystal compound having a cis-1,4-cyclohexyl group.

First claim

The invention claimed is:

1. A composition comprising smectic liquid crystal compounds, each having a 1,4-cyclohexyl group,
wherein the composition contains 0.1 parts by mass to 10 parts by mass of a smectic liquid crystal compound having a cis-1,4-cyclohexyl group relative to 100 parts by mass of a smectic liquid crystal compound having a trans-1,4-cyclohexyl group,
the smectic liquid crystal compound having the trans-1,4-cyclohexyl group and the smectic liquid crystal compound having the cis-1,4-cyclohexyl group are represented by the following formula (1-1) and formula (2-1), respectively:
P 1 -F 1 -B 1 -CyH-G 1 -E 1 -G 2 -E 2 -B 2 -F 2 -P 2   (1-1)

P 1 -F 1 -B 1 -CyH′-G 1 -E 1 -G 2 -E 2 -B 2 -F 2 -P 2   (2-1)

wherein in each of the formulas (1-1) and (2-1):
P 1 and P 2 each independently represent a polymerizable group, P 1 in the formula (1-1) and P 1 in the formula (2-1) are identical groups, and P 2 in the formula (1-1) and P 2 in the formula (2-1) are identical groups;
at least one of F 1 and F 2 represents a C6-C12 linear alkanediyl group, a hydrogen atom contained in the alkanediyl group can be substituted by a halogen atom, and —CH 2 — contained in the alkanediyl group can be substituted by —O—, F 1 in the formula (1-1) and F 1 in the formula (2-1) are identical groups, and F 2 in the formula (1-1) and F 2 in the formula (2-1) are identical groups;
B 1 and B 2 each independently represent a single bond or a bivalent linking group, B 1 in the formula (1-1) and B 1 in the formula (2-1) are identical groups, and B 2 in the formula (1-1) and B 2 in the formula (2-1) are identical groups;
CyH represents a substituted or unsubstituted trans-1,4-cyclohexyl group;
CyH' represents a substituted or unsubstituted cis-1,4-cyclohexyl group;
G 1 and G 2 each independently represent a single bond or a bivalent linking group, G 1 in the formula (1-1) and G 1 in the formula (2-1) are identical groups, and G 2 in the formula ( 1-1) and G 2 in the formula (2-1) are identical groups; and
E 1 and E 2 each independently represent a group selected from a substituted 1,4-phenyl group, an unsubstituted 1,4-phenyl group, a substituted trans-1,4-cyclohexyl group, and an unsubstituted trans-1,4-cyclohexyl group, E 1 in the formula (1-1) and E 1 in the formula (2-1) are identical groups, and E 2 in the formula (1-1) and E 2 in the formula (2-1) are identical groups.

2. The composition as set forth in claim 1 , wherein the smectic liquid crystal compound represented by the formula (1-1) and the compound represented by the formula (2-1) are represented by the following formula (1-2) and formula (2-2), respectively:
P 1 -F 1 -B 1 -CyH-G 1 Ph-G 2 -Ph-B 2 -F 2 -P 2   (1-2)

P 1 -F 1 -B 1 -CyH′-G 1 Ph-G 2 -Ph-B 2 -F 2 -P 2   (2-2)

wherein in each of the formulas (1-2) and (2-2):
P 1 , P 2 , F 1 ,F 2 ,B 1 ,B 2 ,CyH, CyH′, G 1 , and G 2 represent respective groups identical to corresponding ones of the groups representing P 1 , P 2 , F 1 , F 2 , B 2 , B 2 , CyH, CyH′, G 1 , and G 2 in the formulas (1-1) and (2-1); and
Ph represents a substituted or unsubstituted 1,4-phenyl group.

3. The composition as set forth in claim 1 , wherein
B 1 and B 2 each independently represent a single bond or a bivalent linking group represented by —O—; and
G 1 and G 2 each independently represent a bivalent linking group represented by —C(═O)—O—.

4. The composition as set forth in claim 1 , wherein
P 1 and P 2 each independently represent an acryloyloxy group.

5. The composition as set forth in claim 1 , further comprising a dichroic dye.

6. The composition as set forth in claim 5 , wherein
the dichroic dye is a compound represented by the following formula (3-1):
K 1 -L 1 -Ar 1 —N═N—Ar 2 —(N═N—Ar 3 ) p -L 2 -K 2   (3-1):

wherein:
K 1 and K 2 each independently represent a functional group selected from the group consisting of a C1-C12 chain alkyl group, a C5-C6 cyclic alkyl group, an N-piperidinyl group, an N-piperazinyl group, an N-pyrrolidinyl group, an N-morpholinyl group, an N,N-diethylamino group, a cyano group, and a sulfonylmethyl group;
L 1 and L 2 each independently represent a single bond or a bivalent linking group;
Ar 1 through Ar 3 each independently represent (i) a substituted or unsubstituted 1,4-phenylene group, (ii) a substituted or unsubstituted naphthalene-1,4-diyl group, or (iii) a bivalent heterocyclic group which can have a substituent; and
p represents an integer selected from 0 to 2.

7. The composition as set forth in claim 6 , wherein the compound represented by the formula (3-1) is a compound represented by the following formula (3-2):
K 1 -L 1 -Ar 1 —N═N—Ar 2 —N═N—Ar 3 -L 2 -K 2   (3-2)

wherein K 1 ,K 2 ,L 1 ,L 2 ,Ar 1 , Ar 2 ,Ar 3 are same as those of the formula (3-1).

8. The composition as set forth in claim 1 , wherein the composition is a raw material of an optical film.

9. An optical film comprising the composition as set forth in claim 1 , the optical film having a dichroic ratio of equal to or more than 30.

10. An optical film comprising (i) a polymer of the smectic liquid crystal compound having the trans-1,4-cyclohexyl group which is a smectic liquid crystal compound having the trans-1,4-cyclohexyl group contained in the composition as set forth in claim 1 and (ii) a polymer of the smectic liquid crystal compound having the cis-1,4-cyclohexyl group which is a smectic liquid crystal compound having the cis-1,4-cyclohexyl group contained in the composition as set forth in claim 1 ,
the optical film having a dichroic ratio of equal to or more than 30.

11. A method of producing an optical film, comprising the steps of:
(1) applying the composition as set forth in claim 1 to a resin base material so as to shape the composition into a form of a film;
(2) heating the composition which has been thus shaped into the form of a film; and
(3) cooling the composition, which has been thus heated, to a temperature equal to or less than 30° C. so as to subject the composition to smectic liquid crystal alignment.

Assignees

• Sumitomo Chemical Co

Inventors

• Hatanaka Nobuyuki
• Okawa Haruki

Classifications

• C09K19/3068

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

• C09K19/04 Primary

  characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} · CPC title

• C09K19/3086

  in which at least two rings are linked by a chain containing nitrogen atoms · CPC title

• G02B5/3016 Primary

  involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528) · CPC title

• C09D7/41

  Organic pigments; Organic dyes · CPC title