Dichroic dye compound, polarizing film, and uses thereof

Patent metadata

Field	Value
Publication number	US-10514484-B2
Application number	US-201515519346-A
Country	US
Kind code	B2
Filing date	Oct 14, 2015
Priority date	Oct 17, 2014
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

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 a hydrogen atom or the like; R 2 represents a hydrogen atom or the like; R 3 represents a hydrogen atom or the like; Z represents —CO— or the like; and Y represents a group of formula (Y1). In the group of formula (Y1), * represents a bonding site with N, or a group of formula (Y2); and in the group of 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 a hydrogen atom, 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 may be joined together to form a ring containing -N-CO- or -N-SO 2 - together with the nitrogen atom to which they are bond, 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 may be replaced by a halogen atom, a hydroxy group, an amino group, or an amino group having a substituent, -O- or -NR 20 - may be 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 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;
R 3 represents a hydrogen atom, 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 12 )(R 13 ); R 12 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 13 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, R 12 and R 13 may be 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 may be replaced by a halogen atom, a hydroxy group, an amino group, or an amino group having a substituent, -O- or -NR 30 - may be inserted between carbon atoms constituting the alkyl group and the alkoxy group, wherein R 30 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;
Z represents -CO- or -SO 2 -;
Y represents a group of formula (Y1):

wherein * represents a bonding site with N, or a group of formula (Y2):

wherein * represents a bonding site with N; P 1 and P 2 each independently represent -S-, - 0 -, or -N(R 14 )-, wherein R 14 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 the polymerizable liquid crystal compound exhibits a smectic liquid crystal phase.

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

4. A polarizing film comprising the composition according to claim 1 .

5. The polarizing film according to claim 4 , wherein a maximum absorption wavelength (λ max1 ) of the polarizing film is longer than a maximum absorption wavelength (λ max2 ) of the compound represented by formula (1).

6. The polarizing film according to claim 5 , wherein a difference between λ max1 and λ max2 is not less than 10 nm.

7. The polarizing film according to claim 4 , wherein a Bragg peak is exhibited in X-ray diffractometry.

8. A liquid crystal display device comprising the polarizing film according to claim 4 .

9. A liquid crystal cell comprising the polarizing film according to claim 4 , a liquid crystal layer, and a base.

10. The liquid crystal cell according to claim 9 , wherein the polarizing film is disposed between the base and the liquid crystal layer.

11. The liquid crystal cell according to claim 10 , wherein a color filter is further disposed between the base and the liquid crystal layer.

12. A circularly polarizing plate comprising the polarizing film according to claim 4 and a ¼ wavelength plate.

13. An organic EL display device comprising the polarizing film according to claim 4 and an organic EL element.

14. An organic EL display device comprising the circularly polarizing plate according to claim 12 and an organic EL element.

Assignees

• Sumitomo Chemical Co

Inventors

• Hida Noriyuki
• Okawa Haruki

Classifications

• G02F2202/043

  pleochroic · CPC title

• G02F1/13475

  in which at least one liquid crystal cell or layer is doped with a pleochroic dye, e.g. GH-LC cell (G02F1/13476 takes precedence) · CPC title

• C09B43/32

  by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines · CPC title

• C09K19/3852

  Poly(meth)acrylate derivatives · CPC title

• G02B5/3033

  in the form of a thin sheet or foil, e.g. Polaroid · CPC title