Retardation film, composition, method of manufacturing retardation film, polarizing plate and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-2016109757-A1
Application number	US-201514886740-A
Country	US
Kind code	A1
Filing date	Oct 19, 2015
Priority date	Oct 20, 2014
Publication date	Apr 21, 2016
Grant date	—

Abstract

An object of the present invention is to provide a film capable of giving a necessary retardation without degrading the contrast. The present invention provides a retardation film formed from a composition which includes a polymer compound, a rod-like liquid crystal compound and a photo-reactive compound, wherein the polymer compound has a side chain which has one or more azo groups and/or cynnamate groups, and 3 or more and 10 or less arylene groups; the side chain further has an optionally substituted amino group, or a hydrocarbon group at the terminal; an absolute value of difference between an SP value of the polymer compound and an SP value of the photo-reactive compound is 1.1 or less; and an in-plane retardation of the film at wavelength of 550 nm is 10 nm or more and 200 nm or less.

First claim

1 . A retardation film formed from a composition which comprises a polymer compound, a rod-like liquid crystal compound and a photo-reactive compound, wherein the polymer compound has a side chain which has one or more azo groups and/or cynnamate groups, and 3 or more and 10 or less arylene groups; the side chain further has an optionally substituted amino group, or a hydrocarbon group at the terminal; an absolute value of difference between an SP value of the polymer compound and an SP value of the photo-reactive compound is 1.1 or less; and an in-plane retardation of the film at wavelength of 550 nm is 10 nm or more and 200 nm or less.

2 . The retardation film of claim 1 , wherein the polymer compound is represented by Formula IX:

in the formula, R 1 represents a hydrogen atom or methyl group, L represents a single bond, —(CH 2 )O— or —(CH 2 CH 2 O) y —, x is an integer of 2 to 10, y is an integer of 1 to 5, R 2 represents an optionally substituted amino group or hydrocarbon group, and M represents a structure represented by Formula X below:

in the formula, each * represents a bonding site with L or R 2 ; Y represents an azo group, —OCO—, —CO(═O)—, —OCO—CH═CH— or —CH═CH—CO 2 —, m represents an integer of 2 to 9, the plurality of (Y)s may be same or different; and Ar represents an optionally substituted arylene group.

3 . The retardation film of claim 1 , wherein a content of the rod-like liquid crystal compound, relative to 100 parts by mass of the polymer compound, is 0.1 to 40 parts by mass.

4 . The retardation film of claim 1 , wherein a content of the photo-reactive compound, relative to 100 parts by mass of the polymer compound, is 0.1 to 40 parts by mass.

5 . The retardation film of claim 1 , which is a single layered film.

6 . The retardation film of claim 1 , which has an Nz of 0.3 to 0.9, where Nz=(nx−nz)/(nx−ny), nx represents refractive index in in-plane slow axis direction, ny represents refractive index in the in-plane direction normal to nx, and nz represents refractive index in the direction normal to nx and ny.

7 . The retardation film of claim 1 , which has a thickness of 5 μm or less.

8 . A composition comprising a polymer compound, a rod-like liquid crystal compound and a photo-reactive compound, wherein the polymer compound has a side chain which has one or more azo groups and/or cynnamate groups, and 3 or more and 10 or less arylene groups; the side chain further has an optionally substituted amino group, or a hydrocarbon group at the terminal; and an absolute value of difference between an SP value of the polymer compound and an SP value of the photo-reactive compound is 1.1 or less.

9 . A method of manufacturing a retardation film of claim 1 , which comprises coating the composition of claim 8 on a substrate.

10 . The method of manufacturing a retardation film according to claim 9 , which further comprises heating the composition, having been coated on the substrate, at 40° C. or above, and photo-irradiating the composition after heating at a dose of 300 to 30000 mJ/cm 2 .

11 . A polarizing plate comprising a polarizer, and the retardation film of claim 1 .

12 . A liquid crystal display device comprising the retardation film of claim 1 .

13 . The liquid crystal display device of claim 12 , which is an IPS liquid crystal display device.

14 . A retardation film comprising a polymer compound and an alignment controlling agent, wherein the polymer compound has a side chain which has one or more azo groups and/or cynnamate groups and 3 or more and 10 or less of arylene group, the side chain further has an optionally substituted amino group, or a hydrocarbon group at the terminal, a content of the polymer compound in the retardation film is 71% by mass or more, and an in-plane retardation of the film at wavelength of 550 nm is 10 nm or more and 200 nm or less.

15 . The retardation film of claim 14 , wherein the polymer compound is a compound represented by Formula IX:

in the formula, R 1 represents a hydrogen atom or methyl group, L represents a single bond, —(CH 2 ) x O— or —(CH 2 CH 2 O) y —, x is an integer of 2 to 10, y is an integer of 1 to 5, R 2 represents an optionally substituted amino group or hydrocarbon group, and M represents a structure represented by Formula X below:

in the formula, each * represents a bonding site with L or R 2 ; Y represents an azo group, —OCO—, —CO(═O)—, —OCO—CH═CH— or —CH═CH—CO 2 —, m represents an integer of 2 to 9, the plurality of (Y)s may be same or different; and Ar represents an optionally substituted arylene group.

16 . The retardation film of claim 14 , wherein the alignment controlling agent is a compound represented by Formula I below:

in the formula, each R 201 independently represents an aromatic hydrocarbon ring or heterocycle having substituent(s) at least on any of the ortho, meta and para positions, each X 201 independently represents a single bond or —NR 202 —, each R 202 independently represents a hydrogen atom, or alkyl group, alkenyl group, aromatic hydrocarbon cyclic group or heterocyclic group, which may be substituted or unsubstituted.

17 . The retardation film of claim 14 , wherein a content of the alignment controlling agent, relative to 100 parts by mass of the polymer compound, is 0.1 to 20 parts by mass.

18 . The retardation film of claim 14 , which is a single layered film.

19 . The retardation film of claim 14 , which has an Nz value of −0.29 to 0.29;
where, Nz=(nx−nz)/(nx−ny), nx represents refractive index in in-plane slow axis direction, ny represents refractive index in an in-plane direction normal to nx, and nz represents refractive index normal to nx and ny.

20 . The retardation film of claim 14 , which has a thickness of 5 μm or less.

21 . A composition comprising a polymer compound and an alignment controlling agent, wherein the polymer compound has a side chain which has one or more azo groups and/or cynnamate groups, and 3 or more and 10 or less arylene groups; the side chain further has an optionally substituted amino group, or a hydrocarbon group at the terminal; and a content of the polymer compound in the composition is 71% by mass or more relative to the total solid content.

22 . A method of manufacturing a retardation film of claim 14 , which comprises coating the composition of claim 21 over a substrate.

23 . The method of manufacturing a retardation film according to claim 22 , which further comprises heating the composition, having been coated on the substrate, at 40° C. or above, and photo-irradiating the composition after heating at a dose of 300 to 30000 mJ/cm 2 .

24 . A polarizing plate comprising a polarizer, and the retardation film of claim 14 .

25 . A liquid crystal display device comprising the retardation film of claim 14 .

26 . The liquid crystal display device of claim 25 , which is an IPS liquid crystal displa

Assignees

• Fujifilm Corp

Inventors

• Ibaraki Jyunko

Classifications

• C09D4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 · CPC title

• G02B5/3016

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

• G02B5/3083 Primary

  Birefringent or phase retarding elements (G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001) · CPC title

• G02B5/305

  including organic materials, e.g. polymeric layers · CPC title

• C09K19/2007

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