Dichroic dye compound, polarizing film, and uses thereof

Patent metadata

Field	Value
Publication number	US-10160734-B2
Application number	US-201515519250-A
Country	US
Kind code	B2
Filing date	Oct 14, 2015
Priority date	Oct 17, 2014
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

A compound having a maximum absorption in a wavelength range of 350 nm to 550 nm that functions as a dichroic dye is provided. In particular, a compound represented by formula (1) is provided. In the compound of formula (1), R 1 represents an alkyl group having 1 to 20 carbon atoms or the like; R 2 represents an acyl group having 1 to 20 carbon atoms or the like; R 3 represents a hydrogen atom or the like; and Y represents a group of formula (Y1). In the formula (Y1), * represents a bonding site with N, or a group of formula (Y2). In the formula (Y2), * represents a bonding site with N; P 1 and P 2 each independently represent —S— or the like; and Q 1 and Q 2 each independently represent ═N— or the like.

First claim

The invention claimed is:

1. A composition comprising a polymerizable liquid crystal compound and a compound represented by formula (1):

wherein R 1 represents an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms, or —N(R 10 )(R 11 ), wherein R 10 represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, or an arylsulfonyl group having 6 to 20 carbon atoms, R 11 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, R 10 and R 11 are optionally joined together to form a ring containing —N—CO— or —N—SO 2 — together with the nitrogen atom to which they are bonded, at least one hydrogen atom constituting the alkyl group, the alkoxy group, the acyl group, the alkoxycarbonyl group, the acyloxy group, the alkylsulfonyl group, and the arylsulfonyl group is optionally replaced by a halogen atom, a hydroxy group, an amino group, or an amino group having a substituent, and —O— or —NR 20 — is optionally inserted between carbon atoms constituting the alkyl group and the alkoxy group, wherein R 20 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;
R 7 and R 8 are substituents other than a hydrogen atom, each independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, or a cyano group, at least one hydrogen atom constituting the alkyl group having 1 to 4 carbon atoms and the alkoxy group having 1 to 4 carbon atoms is optionally substituted with a halogen atom or a hydroxy group, p and q are each independently an integer from 0 to 2;
R 2 represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, or an arylsulfonyl group having 6 to 20 carbon atoms; R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, R 2 and R 3 are optionally joined together to form a ring containing —N—CO— or —N—SO 2 — together with the nitrogen atom to which they are bonded, at least one hydrogen atom constituting the acyl group, the alkylsulfonyl group, and the arylsulfonyl group is optionally replaced by a halogen atom, a hydroxy group, an amino group, or an amino group having a substituent, and —O— or —NR 21 — is optionally inserted between carbon atoms constituting the alkyl group and the alkoxy group, wherein R 21 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; and
Y represents a group of formula (Y1):

wherein * represents a bonding site with N; R 9 is a substituent other than a hydrogen atom, and independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, or a cyano group, at least one hydrogen atom constituting the alkyl group having 1 to 4 carbon atoms and the alkoxy group having 1 to 4 carbon atoms is optionally substituted with a halogen atom or a hydroxy group; r is an integer from 0 to 2,
or a group of formula (Y2):

wherein * represents a bonding site with N; P 1 and P 2 each independently represent —S—, —O—, or —N(R 12 )—, wherein R 12 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and Q 1 and Q 2 each independently represent ═N— or ═CH—.

2. The composition according to claim 1 , wherein p, q, and r are 0.

3. The composition according to claim 1 , wherein the polymerizable liquid crystal compound exhibits a smectic liquid crystal phase.

4. The composition according to claim 1 , further comprising a polymerization initiator.

5. A polarizing film comprising a compound represented by formula (1):

wherein R 1 represents an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms, or —N(R 10 )(R 11 ), wherein R 10 represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, or an arylsulfonyl group having 6 to 20 carbon atoms, R 11 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, R 10 and R 11 are optionally joined together to form a ring containing —N—CO— or —N—SO 2 — together with the nitrogen atom to which they are bonded, at least one hydrogen atom constituting the alkyl group, the alkoxy group, the acyl group, the alkoxycarbonyl group, the acyloxy group, the alkylsulfonyl group, and the arylsulfonyl group is optionally replaced by a halogen atom, a hydroxy group, an amino group, or an amino group having a substituent, and —O— or —NR 20 — is optionally inserted between carbon atoms constituting the alkyl group and the alkoxy group, wherein R 20 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;
R 7 and R 8 are substituents other than a hydrogen atom, each independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, or a cyano group, at least one hydrogen atom constituting the alkyl group having 1 to 4 carbon atoms and the alkoxy group having 1 to 4 carbon atoms is optionally substituted with a halogen atom or a hydroxy group, p and q are each independently an integer from 0 to 2;
R 2 represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, or an arylsulfonyl group having 6 to 20 carbon atoms; R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, R 2 and R 3 are optionally joined together to form a ring containing —N—CO— or —N—SO 2 — together with the nitrogen atom to which they are bonded, at least one hydrogen atom constituting the acyl group, the alkylsulfonyl group, and the arylsulfonyl group is optionally replaced by a halogen atom, a hydroxy group, an amino group, or an amino group having a substituent, and —O— or —NR 21 — is optionally inserted between carbon atoms constituting the alkyl group and the alkoxy group, wherein R 21 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; and
Y represents a group of formula (Y1):

wherein * represents a bonding site with N; R 9 is a substituent other than a hydrogen atom, and independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, or a cyano group, at least one hydrogen atom constituting the alkyl group having 1 to 4 carbon atoms and the alkoxy group having 1 to 4 carbon atoms is optionally substituted with a halogen atom or a hydroxy group; r is an integer from 0 to 2,
or a group of formula (Y2):

wherein * represents a bonding site with N; P 1 and P 2 each independently represent —S—, —O—, or —N(R 12 )—, wherein R 12 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and Q 1 and Q 2 each independently represent ═N— or ═CH—.

6. A polarizing film formed of the composition according to claim 1 .

7. The

Assignees

• Sumitomo Chemical Co

Inventors

• Hida Noriyuki
• Okawa Haruki

Classifications

• C08K5/55

  Boron-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C07D277/60 Primary

  condensed with carbocyclic rings or ring systems · CPC title

• G02F1/133528

  Polarisers · CPC title

• G02F2202/022

  polymeric · CPC title

• C08K5/23

  Azo-compounds · CPC title