Polymerizable liquid crystal composition, optically anisotropic film, optical film, polarizing plate, image display device, and organic electroluminescent display device

Patent metadata

Field	Value
Publication number	US-11279880-B2
Application number	US-201916423619-A
Country	US
Kind code	B2
Filing date	May 28, 2019
Priority date	Nov 29, 2016
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

A polymerizable liquid crystal composition capable of manufacturing an optically anisotropic film having excellent light fastness; and an optically anisotropic film, an optical film, a polarizing plate, an image display device, and an organic electroluminescent display device, each of which uses the polymerizable liquid crystal composition. The polymerizable liquid crystal composition of an embodiment of the present invention contains a polymerizable liquid crystal compound having reverse-wavelength dispersion properties and an aromatic polyether-based compound.

First claim

What is claimed is:

1. A polymerizable liquid crystal composition comprising:
a polymerizable liquid crystal compound having reverse-wavelength dispersion properties; and
an aromatic polyether compound,
wherein the aromatic polyether compound includes at least one compound selected from the group consisting of Formula (B), Formula (C) and Formula (D), and
wherein the compound represented by Formula (B) is a compound represented by Formula (E) or Formula (F),

in Formula (B), R 1B and R 4B each independently represent a monovalent organic group, R 2B , R 3B , R 5B , and R 6B each independently represent a hydrogen atom or a monovalent substituent, and R 1B and R 2B , R 2B and R 3B , R 3B and R 4B , R 4B and R 5B , R 5B and R 6B , or R 6B and R 1B may be bonded to each other to form a ring,
in Formula (C), R 1C , R 2C , R 6C , and R 7C each independently represent a monovalent organic group, R 3C , R 5C , R 8C and R 11C each independently represent a hydrogen atom or a monovalent substituent, and R 4C , R 9C and R 10C each independently represent a hydrogen atom or a monovalent organic group,
in Formula (D), R 1D represents an alkylene group having 1 to 3 carbon atoms, R 2D , R 3D R 4D , and R 5D each independently represent a hydrogen atom or a monovalent substituent, and R 2D and R 3D , or R 3D and R 4D may be bonded to each other to form a ring,

in Formula (E), R 1E , R 2E , R 3E , R 4E , R 5E , and R 6E each independently represent a hydrogen atom or a monovalent organic group, R 7E , R 9E , and R 10E each independently represent a hydrogen atom or a monovalent substituent, R 8E represents a monovalent organic group, and R 1E and R 2E , or R 3E and R 4E may be bonded to each other to form a ring, and
in Formula (F), R 1F and R 4F each independently represent a monovalent organic group, and R 2F , R 3F , R 5F , and R 6F each independently represent a hydrogen atom or a monovalent substituent.

2. The polymerizable liquid crystal composition according to claim 1 ,
wherein the polymerizable liquid crystal compound is a liquid crystal compound represented by Formula (I),
L 1 -SP 1 -A 1 -D 3 -G 1 -D 1 -Ar-D 2 -G 2 -D 4 -A 2 -SP 2 -L 2   (I)

in Formula (I), D 1 , D 2 , D 3 , and D 4 each independently represent a single bond, —CO—O—, —C(═S)O—, —CR 1 R 2 —, —CR 1 R 2 —CR 3 R 4 —, —O—CR 1 R 2 —, —CR 1 R 2 —O—CR 3 R 4 —, —CO—O—CR 1 R 2 —, —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 —, or —CO—NR 1 —, and R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms,
G 1 and G 2 each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and one or more of —CH 2 —'s constituting the alicyclic hydrocarbon group may be substituted with —O—, —S—, or —NH—,
A 1 and A 2 each independently represent an aromatic ring having 6 or more carbon atoms or a cycloalkylene ring having 6 or more carbon atoms,
SP 1 and SP 2 each independently represent a single bond, a linear alkylene group having 1 to 12 carbon atoms, a branched alkylene group having 3 to 12 carbon atoms, or a divalent linking group in which one or more of —CH 2 —'s constituting the linear alkylene group having 1 to 12 carbon atoms or the branched alkylene group having 3 to 12 carbon atoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—, and Q represents a substituent,
L 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 or L 2 represents a polymerizable group, provided that in a case where Ar is an aromatic ring represented by Formula (Ar-3), at least one of L 1 , L 2 , or L 3 or L 4 in Formula (Ar-3) represents a polymerizable group,
Ar represents any one aromatic ring selected from the group consisting of groups represented by Formulae (Ar-1) to (Ar-5),

here, in Formulae (Ar-1) to (Ar-5), *1 represents a bonding position with D 1 and *2 represents a bonding position with D 2 ,
Q 1 represents N or CH,
Q 2 represents —S—, —O—, or —N(R 5 )—, and R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent,
Z 1 , Z 2 , and Z 3 each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, —NR 6 R 7 , or —SR 8 , R 6 to R 8 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 may be bonded to each other to form an aromatic ring,
A 3 and A 4 each independently represent a group selected from the group consisting of —O—, —N(R 9 )—, —S—, and —CO—, and R 9 represents a hydrogen atom or a substituent,
X represents a hydrogen atom or a non-metal atom of Groups 14 to 16 to which a substituent may be bonded,
D 5 and D 6 each independently represent a single bond, —CO—O—, —C(═S)O—, —CR 1 R 2 —, —CR 1 R 2 —CR 3 R 4 —, —O—CR 1 R 2 —, —CR 1 R 2 —O—CR 3 R 4 —, —CO—O—CR 1 R 2 —, —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 —, or —CO—NR 1 —, and R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms,
SP 3 and SP 4 each independently represent a single bond, a linear alkylene group having 1 to 12 carbon atoms, a branched alkylene group having 3 to 12 carbon atoms, or a divalent linking group in which one or more of —CH 2 —'s constituting the linear alkylene group having 1 to 12 carbon atoms or the branched alkylene group having 3 to 12 carbon atoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—, and Q represents a substituent,
L 3 and L 4 each independently represent a monovalent organic group, and at least one of L 3 , L 4 , or L 1 or L 2 in Formula (I) represents a polymerizable group,
Ax represents an organic group having 2 to 30 carbon atoms, which has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring,
Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms, which has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring,
the aromatic rings in Ax and Ay may have a substituent, and Ax and Ay may be bonded to each other to form a ring, and
Q 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.

3. The polymerizable liquid crystal composition according to claim 2 ,
wherein a compound used for forming the aromatic rings represented by Formulae (Ar-1) to (Ar-5) represented by Ar in Formula (I) is a compound that contains a phenolic structure in which *1 and *2 in Formulae (Ar-1) to (Ar-5) represent hydroxyl groups, and a pKa of the is 5.8 to 10.0.

4. The polymerizable liquid crystal composition according to claim 1 ,
wherein a content of the aromatic polyether compound is 0.1 to 50 parts

Assignees

• Fujifilm Corp

Inventors

• Takahashi Keita
• Nojiri Mayumi
• Muramatsu Ayako

Classifications

• H10K59/8791

  Arrangements for improving contrast, e.g. preventing reflection of ambient light · CPC title

• C09K19/3814 Primary

  Polyethers · CPC title

• C09K19/3086 Primary

  in which at least two rings are linked by a chain containing nitrogen atoms · CPC title

• C07D311/72

  3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols · CPC title

• C07D317/54

  Radicals substituted by oxygen atoms · CPC title