Polymerizable compound and optically anisotropic body

Patent metadata

Field	Value
Publication number	US-10723952-B2
Application number	US-201515517441-A
Country	US
Kind code	B2
Filing date	Oct 6, 2015
Priority date	Oct 9, 2014
Publication date	Jul 28, 2020
Grant date	Jul 28, 2020

Abstract

The present invention provides a polymerizable compound that reduces, for example, the likelihood of crystals precipitating in a polymerizable composition including the polymerizable compound and enables the polymerizable composition to have high preservation stability and a polymerizable composition including the polymerizable compound which reduces the likelihood of inconsistencies being formed in a film-like polymer produced by polymerizing the polymerizable composition. Also provided are a polymer produced by polymerizing the polymerizable composition and an optically anisotropic body including the polymer. The present invention provides the compound represented by General Formula (I), a composition including the compound, a polymer produced by polymerizing the composition, and an optically anisotropic body including the polymer.

First claim

The invention claimed is:

1. A compound represented by General Formula (I) below,

wherein, P represents a polymerizable group selected from the group consisting of groups represented by Formulae (P-1) to (P-20) below,

S represents an alkylene group having 1 to 20 carbon atoms and 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 —COO—, —OCO—, —OCO—O—, —CO—NH— or —NH—CO;
X 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 —, —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—, —N═N—, —CH═N—N═CH—, or a single bond and, when a plurality of X groups are present, they may be identical to or different from one another in which P—(S—X) k — does not include an —O—O— bond;
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, the above groups may be optionally substituted with one or more L substituents, and, when a plurality of A 1 groups and/or a plurality of A 2 groups are present, they may be identical to or different from one another;
L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro 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—, when a plurality of L substituents are present, they may be identical to or different from one another, and some hydrogen atoms included in the alkyl group may be replaced with fluorine atoms;
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 —, —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—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, or a single bond, and, when a plurality of Z 1 groups and/or a plurality of Z 2 groups are present, they may be identical to or different from one another;
M represents a group selected from Formulae (M-1) to (M-8) below,

the above groups may be optionally substituted with one or more L M substituents, L M 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—, some hydrogen atoms included in the alkyl group may be replaced with fluorine atoms, and, when a plurality of L M substituents are present, they may be identical to or different from one another;
R 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a cyano group, a nitro group, an isocyano 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—, and some hydrogen atoms included in the alkyl group may be replaced with fluorine atoms;
G represents a group selected from Formulae (G-1) and (G-2) below,

wherein, R 2 represents a hydrogen atom 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—, or —NH—CO—, and some hydrogen atoms included in the alkyl group may be replaced with fluorine atoms;
W 1 represents a group having 2 to 30 carbon atoms, the group including at least one aromatic group, the group may be optionally substituted with one or more L W substituents, L W 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 —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, or —NH—CO—, some hydrogen atoms included in the alkyl group may be replaced with fluorine atoms, and, when a plurality of L W substituents are present, they may be identical to or different from one another;
W 2 represents a linear or branched alkyl group having 1 to 20 carbon atoms, the group may be optionally substituted with one or more L W substituents; and
k represents an integer of 0 or 1, m1 and m2 each independently represent an integer of 0 to 4, and m1+m2 is an integer of 1 to 5.

2. The compound according to claim 1 , wherein, in General Formula (I), S independently 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—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, or —C≡C—.

3. The compound according to claim 1 , wherein, in General Formula (I), a total number of π electrons included in W 1 and W 2 is 4 to 24.

4. The compound according to claim 1 , wherein, in General Formula (I), the group represented by W 1 is a group represented by any one of Formulae (W-1) to (W-19) below,

wherein, the above groups may have a bond at any position;
Q 1 represents —O—, —S—, —NR 3 — (where R 3 represents a hydrogen atom o

Assignees

• Dainippon Ink & Chemicals

Inventors

• Horiguchi Masahiro
• Kadomoto Yutaka
• Kusumoto Tetsuo

Classifications

• C07C251/88

  having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines · CPC title

• C07D277/50

  Nitrogen atoms bound to hetero atoms · CPC title

• C07C251/86

  having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C255/55

  containing cyano groups and esterified hydroxy groups bound to the carbon skeleton · CPC title

• A61K8/4966

  Triazines or their condensed derivatives · CPC title