Polymerizable composition and optically anisotropic body produced using the same

Patent metadata

Field	Value
Publication number	US-10927263-B2
Application number	US-201716317963-A
Country	US
Kind code	B2
Filing date	Jul 13, 2017
Priority date	Jul 15, 2016
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

An object of the present invention is to provide a polymerizable composition with which a polymer having a high degree of hardness can be produced. Another object is to provide, for example, an optically anisotropic body, a phase retardation film, an optical compensation film, an antireflection film, a lens, and a lens sheet that are composed of the polymerizable composition and a liquid crystal display element, an organic light-emitting display element, a lighting element, an optical component, a coloring agent, a security marker, a laser emission member, a polarizing film, a coloring material, and a printed item that are produced using the polymerizable composition. The present invention provides a polymerizable composition including a polymerizable compound represented by General Formula (IA) which has a specific structure including a plurality of polymerizable groups.

First claim

The invention claimed is:

1. A polymerizable composition comprising a compound represented by Formula (IA) below:

in Formula (IA), P 3 represents a polymerizable group selected from Formulae (P-1) to (P-3) below:

Sp 3 represents a spacer group and, when a plurality of Sp 3 groups are present, they may be identical to or different from one another,
wherein Sp 3 represents an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — group or two or more —CH 2 — groups that are not adjacent to one another may be each independently replaced with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—;
X 3 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond and, when a plurality of X 3 groups are present, they may be identical to or different from one another, P 3 -(Sp 3 -X 3 ) k3 — does not include an —O—O— linkage;
k3 represents an integer of 1 to 10;
A 1 and A 2 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, and the above groups may be optionally substituted with one or more L substituents;
L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — group or two or more —CH 2 — groups that are not adjacent to one another may be each independently replaced with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, where a hydrogen atom included in the alkyl group may be replaced with a fluorine atom, and, when a plurality of L substituents are present in the compound, they may be identical to or different from one another;
Z 1 and Z 2 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, when a plurality of Z 1 groups are present, they may be identical to or different from one another, and, when a plurality of Z 2 groups are present, they may be identical to or different from one another; m1 and m2 each independently represent an integer of 0 to 6, and m1+m2 is an integer of 0 to 6;
Y represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — group or two or more —CH 2 — groups that are not adjacent to one another may be each independently replaced with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, or where a hydrogen atom included in the alkyl group may be replaced with a fluorine atom;
R 1 represents a group represented by P 1 -(Sp 1 -X 1 ) k1 — wherein, P 1 represents a polymerizable group; Sp 1 represents a spacer group and, when a plurality of Sp 1 groups are present, they may be identical to or different from one another; X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond and, when a plurality of X 1 groups are present, they may be identical to or different from one another, P 1 -(Sp 1 -X 1 ) k1 — does not include an —O—O— linkage; and k1 represents an integer of 0 to 10; and
R 2 represents a group represented by P 2 -(Sp 2 -X 2 ) k2 — wherein, P 2 represents a polymerizable group; Sp 2 represents a spacer group and, when a plurality of Sp 2 groups are present, they may be identical to or different from one another; X 2 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond and, when a plurality of X 2 groups are present, they may be identical to or different from one another, P 2 -(Sp 2 -X 2 ) k2 — does not include an —O—O— linkage; and k2 represents an integer of 0 to 10,
the polymerizable composition further comprising a polymerizable compound represented by Formula (1-1) below which includes one polymerizable group and/or a polymerizable compound represented by Formula (2-1) below which includes two polymerizable groups:

in Formula (1-1),
P 11 represents a polymerizable group;
S 11 represents a spacer group or a single bond and, when a plurality of S 11 groups are present, they may be identical to or different from one another;
X 11 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond and, when a plurality of X 11 groups are present, they may be identical to or different from one another, P 11 —(S 11 —X 11 ) m11 — does not include an —O—O—; m11 represents an integer of 0 to 8;
MG 11 represents Formula (1-a) below:

in Formula (1-a), A 11 an

Assignees

• Dainippon Ink & Chemicals

Inventors

• Endo Kouichi
• Kuwana Yasuhiro
• TAKASAKI Mika

Classifications

• H10K50/86

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

• C07D277/82 Primary

  Nitrogen atoms · CPC title

• C08F220/365

  containing further carboxylic moieties · CPC title

• C09D4/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08F20/38 Primary

  Esters containing sulfur · CPC title