Azo compound and salt thereof, and dye-based polarizing film and polarizing plate containing the same

Patent metadata

Field	Value
Publication number	US-9244194-B2
Application number	US-201213983791-A
Country	US
Kind code	B2
Filing date	Feb 6, 2012
Priority date	Feb 7, 2011
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

Abstract

The present invention relates to an azo compound represented by the following formula (1) [wherein, A represents a naphthyl group having a substituent, R 1 to R 6 each independently represent a hydrogen atom, an alkyl group having a carbon atom number of 1 to 5, an alkoxy group having a carbon atom number of 1 to 5, a sulfo group, or an alkoxy group having a sulfo group and a carbon atom number of 1 to 5, and X represents a benzoylamino group having a substituent, a phenylamine group having a substituent, a phenylazo group having a substituent, or a naphthotriazole group having a substituent] and a salt thereof. A neutral color polarizing plate and a color polarizing plate for a liquid crystal projector being excellent in polarization performance and durability and having less color leakage in a visible light region can be provided.

First claim

The invention claimed is:

1. A dye-based polarizing film containing in a raw film for a polarizing film, an azo compound and/or a salt thereof, which is represented by the following formula (7):

in the formula (7), A represents a naphthyl group having a substituent; R 1 to R 6 each independently represent a hydrogen atom, an alkyl group having a carbon atom number of 1 to 5, an alkoxy group having a carbon atom number of 1 to 5, a sulfo group or an alkoxy group having a sulfo group and a carbon atom number of 1 to 5, X represents a phenylamino group, a phenylazo group, or a naphthotriazole group,
wherein A is a naphthyl group represented by the following formula (6):

in the formula (6), R 13 represents a hydrogen atom, a sulfo group, a hydroxy group, or an alkoxy group having a sulfo group and a carbon atom number of 1 to 5, and n represents 1 to 3;
wherein the phenylamino group is represented by the following formula (2):

in the formula (2), R 7 and R 8 each independently represent a hydrogen atom, a methyl group, a methoxy group, a sulfo group, an amino group or a substituted amino group;
wherein the phenylazo group is represented by the following formula (5):

in the formula (5), R 10 to R 12 each independently represent a hydrogen atom, a hydroxy group, an alkyl group having a carbon atom number of 1 to 5, an alkoxy group having a carbon atom number of 1 to 5, an amino group or a substituted amino group; and
wherein the naphthotriazole group is represented by the following formula (4):

in the formula (4), m represents 1 or 2.

2. The dye-based polarizing film containing the azo compound and/or a salt thereof according to claim 1 , wherein R 1 to R 6 are each independently a hydrogen atom, a methyl group, a methoxy group, or an alkoxy group having a sulfo group and a carbon atom number of 1 to 5.

3. The dye-based polarizing film containing the azo compound and/or a salt thereof according to claim 1 , wherein A is a naphthyl group substituted with 2 or 3 sulfo groups (m represents 2), or a naphthyl group substituted with a 3-sulfopropoxy group and a sulfo group (R 13 is a 3-sulfopropoxy group and n represents 1); R 1 , R 3 and R 5 are each independently a hydrogen atom, a methyl group, a methoxy group or a 3-sulfopropoxy group; R 2 , R 4 and R 6 are methyl groups; and X is any one group selected from the group consisting of an unsubstituted phenylamino group (R 7 and R 8 are hydrogen atoms), a phenylamino group substituted with a methoxy group (one of R 7 and R 8 is a methoxy group and the other is a hydrogen atom), or a naphthotriazole substituted with 2 sulfo groups (m=2).

4. The dye-based polarizing film containing at least one kind of the azo compound and/or a salt thereof according to claim 3 and one or more kinds of other dichroic organic dyes.

5. The dye-based polarizing film containing two or more kinds of the azo compound and/or a salt thereof according to claim 3 and one or more kinds of other dichroic organic dyes.

6. The dye-based polarizing film according to claim 3 , wherein the raw film for a polarizing film is a film comprising a polyvinyl alcohol resin, a vinyl alcohol copolymer resin or a modified form of a polyvinyl alcohol resin.

7. The dye-based polarizing film according to claim 6 , wherein the raw film for a polarizing film is a polyvinyl alcohol resin film.

8. A dye-based polarizing plate with a transparent protective film attached to at least one surface comprising the dye-based polarizing film according to claim 3 .

9. A liquid crystal display comprising the dye-based polarizing plate according to claim 8 .

10. The dye-based polarizing film containing at least one kind of the azo compound and/or a salt thereof according to claim 1 and at least one or more kinds of other dichroic organic dyes.

11. The dye-based polarizing film containing at least two or more kinds of the azo compound and/or a salt thereof according to claim 1 and one or more kinds of other dichroic organic dyes.

12. The dye-based polarizing film containing at least one kind of the azo compound and/or a salt thereof according to claim 1 is a color dye-based polarizing film.

13. The dye-based polarizing film according to claim 1 , wherein the raw film for a polarizing film is a film comprising a polyvinyl alcohol resin, a vinyl alcohol copolymer resin or a modified form of a polyvinyl alcohol resin.

14. The dye-based polarizing film according to claim 13 , wherein the raw film for a polarizing film is a polyvinyl alcohol resin film.

15. A dye-based polarizing plate with a transparent protective film attached to at least one surface comprising the dye-based polarizing film according to claim 1 .

16. A liquid crystal display comprising the dye-based polarizing plate according to claim 15 .

17. A liquid crystal projector comprising the dye-based polarizing film according to claim 1 or a dye-based polarizing plate with a transparent protective film attached to at least one surface of said dye-based polarizing film.

Assignees

• Higeta Takahiro
• Nishiguchi Takuto
• Nippon Kayaku Kk
• Polatechno Co Ltd

Inventors

• Higeta Takahiro
• Nishiguchi Takuto

Classifications

• C09B67/0046

  Mixtures of two or more azo dyes · CPC title

• Y10T428/1041

  Cross-Sectional Technologies · mapped topic

• C09B49/04

  from amino compounds of the benzene, naphthalene or anthracene series · CPC title

• G02F1/133533

  Colour selective polarisers (G02F1/1347 takes precedence) · CPC title

• G02B1/04 Primary

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title