Optically anisotropic layer, method of manufacturing the same, laminate, method of manufacturing the same, polarizing plate, liquid crystal display device, and organic EL display device

Patent metadata

Field	Value
Publication number	US-10048416-B2
Application number	US-201414482292-A
Country	US
Kind code	B2
Filing date	Sep 10, 2014
Priority date	Sep 11, 2013
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

To suppress a phenomenon where an optical axis of the optically anisotropic layer is tilted when the optically anisotropic layer is produced by using a liquid crystalline compound showing smectic phase as a materials showing a higher level of orderliness. An optically anisotropic layer wherein a polymerizable composition, containing one or more polymerizable rod-like liquid crystal compound showing a smectic phase, is fixed in a state of smectic phase, and a direction of maximum refractive index of the optically anisotropic layer is inclined at 10° or smaller to the surface of the optically anisotropic layer, a method for manufacturing the same, a laminate and a method for manufacturing the same, a polarizing plate, a liquid crystal display device, and an organic EL display device.

First claim

What is claimed is:

1. An optically anisotropic layer wherein a polymerizable composition, containing one or more polymerizable rod-like liquid crystal compound showing a smectic phase, is fixed in a state of smectic phase, and a direction of maximum refractive index of said optically anisotropic layer is inclined at 10° or smaller to the surface of said optically anisotropic layer,
wherein the polymerizable rod-like liquid crystal compound is a compound represented by the formula (II);
L 1 -G 1 -D 1 -Ar-D 2 -G 2 -L 2   Formula (II):

where, Ar represents a divalent aromatic ring group represented by the formulae (II-1), (II-2), (II-3) or (II-4) below;
each of D 1 and D 2 independently represents —CO—O—, —O—CO—, —C(═S)O—, —O—C(═OS)—, —CR 1 R 2 —, —CR 1 R 2 —CR 3 R 4 —, —O—CR 1 R 2 —O—, —CR 1 R 2 —O—CR 3 R 4 —, —CR 1 R 2 —O—CO—, —O—CO—CR 1 R 2 —, —CR 1 R 2 —O—CO—CR 3 R 4 —, —CR 1 R 2 —CO—O—CR 3 R 4 —, —NR 1 —CR 2 R 3 —, —CR 1 R 2 —NR 3 —, —CO—NR 2 —, or —NR 1 —CO—; each of R 1 , R 2 , R 3 and R 4 independently represents a hydrogen atom, halogen atom, or C 1-4 alkyl group;
each of G 1 and G 2 independently represents a C 5-8 divalent alicyclic hydrocarbon group, a methylene group contained in the alicyclic hydrocarbon group may be substituted by —O—, —S—, —NH— or —N(R)—;
each of L 1 and L 2 independently represents a monovalent organic group, and at least one selected from the group consisting of L 1 and L 2 represents a monovalent group having a polymerizable group,

in the formula (II-1), Q 1 represents —S—, —O— or —NR 11 —, where R 11 represents a hydrogen atom or C 1-6 alkyl group;
Y 1 represents a C 6-12 aromatic hydrocarbon group, or, C 3-12 aromatic heterocyclic group;
each of Z 1 and Z 2 independently represents a hydrogen atom or C 1-20 aliphatic hydrocarbon group, C 3-20 alicyclic hydrocarbon group, monovalent C 6-20 aromatic hydrocarbon group, halogen atom, cyano group, nitro group, —NR 12 R 13 or —SR 12 , Z 1 and Z 2 may combine with each other to form an aromatic ring or aromatic heterocycle, each of R 12 and R 13 independently represents a hydrogen atom or C 1-6 alkyl group;
in the formula (II-2), each of A 1 and A 2 independently represents a group selected from the group consisting of —O—, —NR—, —S— and —CO—, where R represents a hydrogen atom or substituent;
X represents a Group-XIV to XVI nonmetal atom, where, X may have a hydrogen atom or substituent bound thereto, and each of Z 1 and Z 2 independently represents a substituent;
in the formula (II-3) and the formula (II-4), Ax represents an C 2-30 organic group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and aromatic heterocycle, Ay represents a hydrogen atom, a C 1-6 alkyl group which may have a substituent, or, a C 2-30 organic group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and aromatic heterocycle; the aromatic ring contained in Ax and Ay may have a substituent; Ax and Ay may combine together to form a ring;
each of Z 1 , Z 2 and Z 3 independently represents a hydrogen atom or substituent; and
Q 2 represents a hydrogen atom, or, C 1-6 alkyl group which may have a substituent, and
wherein the polymerizable composition comprises two or more different polymerizable rod-like liquid crystal compounds represented by the formula (II).

2. The optically anisotropic layer of claim 1 , wherein the optically anisotropic layer has a thickness d of 1000 to 5000 nm, Re(550) of 10 to 400 nm, Re(550)/d of 0.01 to 0.1 where both of d and Re(550) are given in nm, and a contrast of 100,000 or larger and 200,000 or smaller.

3. The optically anisotropic layer of claim 1 , wherein a ratio of the polymerizable rod-like liquid crystal compound which remains unpolymerized is 5% by mass or less.

4. The optically anisotropic layer of claim 1 , wherein the polymerizable rod-like liquid crystal compound has a molecular weight of 1300 or smaller.

5. The optically anisotropic layer of claim 1 , wherein the direction of maximum refractive index of the optically anisotropic layer is inclined at 0° or larger and 3° or smaller to the surface of the optically anisotropic layer.

6. A method of manufacturing the optically anisotropic layer of claim 1 , which comprises steps of heating a layer which is provided on a support and is composed of a polymerizable composition which contains a polymerizable rod-like liquid crystal compound, up to or above the phase transition temperature between the smectic liquid crystal phase and the nematic liquid crystal phase, and cooling the layer to a temperature 5° C. or more lower than the phase transition temperature, followed by polymerization.

7. An organic EL display device comprising the optically anisotropic layer of claim 1 .

8. The optically anisotropic layer of claim 1 , wherein the polymerizable rod-like liquid crystal compound is a compound represented by the formula (I):
Q 1 -SP 1 —X 1 -M 1 -(Y 1 -L-Y 2 -M 2 ) n -X 2 —SP 2 -Q 2   Formula (I):

where, n is an integer representing the number of repetition of (Y 1 -L-Y 2 -M 2 ) which is 0 or more,
each of Q 1 and Q 2 represents a polymerizable group,
each of SP 1 and SP 2 represents a straight-chain or branched alkylene group, or a group composed of a combination of straight-chain or branched alkylene, with at least either of —O— and —C(═O)—, having 2 to 8 carbon atoms in total;
each of X 1 and X 2 represents a single bond or oxygen atom;
—Y 1 -L-Y 2 — represents a straight-chain alkylene group, or, a group composed of a combination of straight-chain alkylene group with —O— and/or —C(═O)—, having 3 to 18 carbon atoms in total;
M 1 is a group represented by
—Ar 1 —COO—Ar 2 —COO—Ar 3 —COO—

or
—Ar 1 —COO—Ar 2 —COO—Ar 3 —

or
—Ar 1 —COO—Ar 2 —Ar 3 —;

M 2 is a group represented by
—Ar 3 —OCO—Ar 2 —OCO—Ar 1 —OCO—

or
—Ar 3 —OCO—Ar 2 —OCO—Ar 1 —

or
—Ar 3 —OCO—Ar 2 —Ar 1 —; and

each of Ar 1 , Ar 2 and Ar 3 independently represents phenylene or biphenylene.

9. The optically anisotropic layer of claim 8 , wherein the polymerizable rod-like liquid crystal compound represented by the formula (1) satisfies at least any one of a to c below:
a: At least either one of Q 1 and Q 2 represents a ring-opening polymerizable group,
b: Each of SP 1 and SP 2 contains an alkylene oxide unit,
c: n is 1 or larger.

10. The optically anisotropic layer of claim 1 , wherein a polymerizable composition, containing two or more polymerizable rod-like liquid crystal compounds represented by the formula (II), is fixed, and a transition temperature from the smectic phase to the nematic phase of the composition is 80° C. or lower.

11. The optically anisotropic layer of claim 10 , wherein a polymerizable composition, containing one or more polymerizable rod-like liquid crystal compound, is fixed in a state of nematic phase, and a direction of maximum refractive index of said optically anisotropic layer is inclined at 10° or smaller to the surface of the optically anisotropic layer.

12. The optically anisotropic layer of claim 1 , wherein the polymerizable composition further contains 1% by mass or more and 50% by mass or less of a polymerizable rod-like compound represented by the formula (2);
Q 3 -SP 3 —X 3 -M 3 -(Y 3 -L-Y 4 -M 4 ) m -X 4 —SP 4 -Q 4   Formula (2):

where, m is an integer representing the number of repetition of (Y 3 -L-Y 4 -M 4 ) whic

Assignees

• Fujifilm Corp

Inventors

• Muramatsu Ayako
• Sakai Shinnosuke
• Niori Teruki
• Morishima Shinichi

Classifications

• C09K19/2007

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

• C09K2019/3077

  Cy-Cy-COO-Ph · CPC title

• C09K19/3497

  the heterocyclic ring containing sulfur and nitrogen atoms · CPC title

• C09K19/24

  linked by a chain containing nitrogen-to-nitrogen bonds · CPC title

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title