Polymerizable compound and optically anisotropic body

Patent metadata

Field	Value
Publication number	US-11046889-B2
Application number	US-201616060265-A
Country	US
Kind code	B2
Filing date	Dec 1, 2016
Priority date	Dec 8, 2015
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

The polymerizable liquid crystal compound has reverse wavelength dispersion or low wavelength dispersion and has high solubility in various solvents. The polymerizable liquid crystal compound provides an optically anisotropic body having high adhesiveness to substrates (or alignment films), by adding the polymerizable liquid crystal compound to a polymerizable composition and polymerizing the polymerizable composition using ultraviolet light. The invention provides a polymerizable composition containing the polymerizable liquid crystal compound having reverse wavelength dispersion or low wavelength dispersion, a polymer obtained by polymerizing the polymerizable composition, and an optically anisotropic body using the polymer. The present invention provides a polymerizable low wavelength dispersion or polymerizable reverse wavelength dispersion compound having in the molecule a partial structure represented by the general formula (AO-1); and also provides a composition containing the compound, a polymer obtained by polymerizing the composition, and an optically anisotropic body and the like using the polymer.

First claim

The invention claimed is:

1. A polymerizable low wavelength dispersion or polymerizable reverse wavelength dispersion compound having a partial structure represented by the following general formula (AO-1) in a molecule:

wherein n 0 represents an integer of 2 or more; and R 0 represents a linear alkylene group having 2 to 20 carbon atoms, a branched alkylene group having 3 to 20 carbon atoms, an arbitrary hydrogen atom in the alkylene group may be substituted with a fluorine atom or a chlorine atom, and plural les may be the same or different,
wherein the compound has, in a molecule, at least one group represented by the following general formula (I-0-R):

wherein P 0 represents a polymerizable group; k 0 represents an integer of 1 to 10; Sp 0 represents a linear alkylene group having 1 to 30 carbon atoms, a branched alkylene group having 3 to 30 carbon atoms, or a single bond, one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other in the alkylene group may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C, and plural Sp 0 's, if any, may be the same or different; and (Sp 0 ) k0 may be a group having a partial structure represented by the general formula (AO-1), provided that P 0 —(Sp 0 ) k0 —contains no —O—O— bond,
wherein the compound is represented by the general formula (I):

wherein R 1 is the group represented by the general formula (I-0-R) in which)(Sp 0 ) k0 includes the partial structure represented by the general formula (AO-1), and
wherein R 2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted 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 —, —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—, or —CH═N—N═CH—;
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 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more substituents L's, L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl 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, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH— or —NH—CO—, and an arbitrary hydrogen atom in the alkyl group may be substituted with a fluorine atom, and plural L's in the compound, if any, may be the same or different;
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, plural Z 1 's, if any, may be the same or different, and plural Z 2 's, if any, may be the same or different;
G 1 represents a divalent group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heteroring, the number of π electrons contained in the aromatic ring(s) in the group represented by G 1 is 12 or more, and the group represented by G 1 may be unsubstituted or substituted with one or more substituents L G 's, L G represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl 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, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted 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—, and an arbitrary hydrogen atom in the alkyl group may be substituted with a fluorine atom, or L G may represent a group represented by P LG —(Sp LG —X LG ) kLG — where P LG represents a polymerizable group, Sp LG represents a linear alkylene group having 1 to 10 carbon atoms in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— or a single bond, plural Sp LG 's, if any, may be the same or different, X LG 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, plural X LG 's, if any, may be the same or different, and kLG represents an integer of 0 to 10, and plural L G 's in the compound, if any, may be the same or different; and
m1 and m2 each independently represent an integer of 0 to 6, provided that m1+m2 is an integer of 0 to 6;
provided that the general formula (I) contains no —O—O— bond,
wherein in the general formula (I), G 1 represents a group selected from the following general formulae (M-1) to (M-6):

wherein these groups may be unsubstituted or substituted with one or more substituents L G 's as described above; arbitrary (—CH═)'s may be each independently substituted with —N═; (—CH 2 —)'s each independently represent —O—, —S—, —NR T —, wherein R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, —CS—, or —CO—; T 1 represents a group selected from the following formulae (T1-1) to (T1-6):

wherein these groups may have a bonding at an arbitrary posi

Assignees

• Dainippon Ink & Chemicals

Inventors

• Saito Yoshitaka
• Yamazaki Tatsufumi
• Horiguchi Masahiro
• Mamiya Junichi
• Tsuruta Toru

Classifications

• C08F222/1035

  of aromatic trialcohols · CPC title

• C08F222/1025

  of aromatic dialcohols · CPC title

• C07D277/64

  with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• G02F1/133633

  using mesogenic materials · CPC title