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

Patent metadata

Field	Value
Publication number	US-9678384-B2
Application number	US-201514886740-A
Country	US
Kind code	B2
Filing date	Oct 19, 2015
Priority date	Oct 20, 2014
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

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

The invention claimed is:

1. A retardation film formed from a composition which comprises:
a polymer compound,
wherein the polymer compound is represented by Formula IX or Formula XI:

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;

in the formula XI, R 1 represents a hydrogen atom or methyl group; L represent a single bond, —(CH 2 ) x O—, x is an integer of 2 to 10, or —(CH 2 CH 2 O) y —, y is an integer of 1 to 6; each of R 2 and R 3 independently represents a hydrogen atom, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 9 carbon atoms, or optionally substituted amino group; each of Y 1 and Y 2 independently represents an azo group, —OCO—CH═CH—, or —CH═CH—CO 2 —; and each of m1 and m2 independently represents an integer of 1 or 2, when m1 or m2 represents 2, the plurality of (Y 1 )s or (Y 2 )s may be same or different;
a rod-like liquid crystal compound,
wherein said rod-like liquid crystal compound is composed having a structure represented by Formula (I):
Q1-SP1-X1-M 1 -(Y1-L-Y2-M 2 ) n -X2-SP2-Q2,  Formula (I):

wherein
n is an integer of 0 to 3, which denotes the number of repetition of (Y1-L-Y2-M 2 ),
each of Q1 and Q2 represents a polymerizable group, and each of the polymerizable groups Q1 and Q2 is preferably one of an acryloyl group, methacryloyl group, radical polymerizable group or ring-opened polymerizable group,
each of SP1 and SP2 represents one of a straight-chain or branched alkylene group, or a group composed of a straight-chain or branched alkylene group combined with at least one of —O— and —C(═O)—, having a total number of carbon atoms of 2 to 8 in integer;
each of X1 and X2 represents a single bond or oxygen atom;
—Y1-L-Y2- represents one of a straight-chain alkylene group, or a group composed of straight-chain alkylene group and —O— and/or —C(═O)—, having a total number of carbon atoms of 3 to 18 in integer; and
each of M 1 and M 2 configures a mesogenic group, including a group having one of a rod-like or plate-like rigid structure,
M 1 is a group represented by one of —Ar1-COO—Ar2-COO—Ar3-COO— or —Ar1-COO—Ar2-COO—Ar3- or —Ar1-COO—Ar2-Ar3-;
M 2 is a group represented by one of —Ar3-OCO—Ar2-OCO—Ar1-OCO— or —Ar3-OCO—Ar2-OCO—Ar1- or —Ar3-OCO—Ar2-Ar1-; and
each of Ar1, Ar2 and Ar3 independently represents phenylene or biphenylene substituted by an arbitrary number of bromine atom(s), methyl group(s), or methoxy group(s), 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 ) 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.

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,
wherein the polymer compound is represented by Formula IX or Formula XI:

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;

in the formula XI, R 1 represents a hydrogen atom or methyl group; L represent a single bond, —(CH 2 ) x O—, x is an integer of 2 to 10, or —(CH 2 CH 2 O) y —, y is an integer of 1 to 6; each of R 2 and R 3 independently represents a hydrogen atom, alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 9 carbon atoms, or optionally substituted amino group; each of Y 1 and Y 2 independently represents an azo group, —OCO—CH═CH—, or —CH═CH—CO 2 —; and each of m1 and m2 independently represents an integer of 1 or 2, when m1 or m2 represents 2, the plurality of (Y 1 )s or (Y 2 )s may be same or different;
a rod-like liquid crystal compound and a photo-reactive compound,
wherein said rod-like liquid crystal compound is composed having a structure represented by Formula (I):
Q1-SP1-X1-M 1 -(Y1-L-Y2-M 2 ) n -X2-SP2-Q2,  Formula (I):

wherein
n is an integer of 0 to 3, which denotes the number of repetition of (Y1-L-Y2-M 2 ),
each of Q1 and Q2 represents a polyme

Assignees

• Fujifilm Corp

Inventors

• Ibaraki Jyunko

Classifications

• C09K19/3486

  the heterocyclic ring containing nitrogen and oxygen atoms · CPC title

• C09K19/56

  Aligning agents · CPC title

• Y10T428/1036

  Cross-Sectional Technologies · mapped topic

• Y10T428/10

  Cross-Sectional Technologies · mapped topic

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title