Polymerizable compound and optically anisotropic body

Patent metadata

Field	Value
Publication number	US-10647662-B2
Application number	US-201615542552-A
Country	US
Kind code	B2
Filing date	Jan 7, 2016
Priority date	Jan 16, 2015
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

In light of requests to reduce or reverse the wavelength dispersion of the birefringence of a phase-retardation film in order to increase the viewing angle of a liquid crystal display, 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. Another object of the present invention is to provide a polymer produced by polymerizing the polymerizable 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 A 1 and A 2 each independently represent a 1,4-phenylene group, or a 1,4-cyclohexylene group; the above groups may be optionally substituted with one or more L substituents; 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, 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 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, they may be identical to or different from one another,
wherein Z 1 and Z 2 each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, 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,
wherein m1 and m2 each independently represent an integer of 0 to 5; and m1+m2 is an integer of 1 to 5, wherein M represents a group selected from Formulae (M-1) to (M-2) below;

the above groups may have a bond at any position; 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—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or where a hydrogen atom included in the alkyl group may be replaced with a fluorine atom; and, when a plurality of L M substituents are present, they may be identical to or different from one another,
wherein G represents a group selected from Formulae (G-1) and (G-2) below;

(wherein in formulae (G-1) and (G-2), W2 corresponds to R4 in Formula (I), Y represents a hydrogen atom;
W 1 represents,

W 2 represents R 4 ;
wherein R 1 represents a group represented by P 1 -(Sp 1 -X 1 ) k1 — (where 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—, —OCF 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 —OCO—, —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— bond); and k1 represents an integer of 0 to 10),
wherein R 2 represents a group represented by P 2 —(Sp 2 -X 2 ) k2 — (where 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 —OCO—, —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— bond); and k2 represents an integer of 0 to 10),
wherein R 3 represents a hydrogen atom,
wherein R 4 represents a group represented by P 4 —(Sp 4 -X 4 ) k4 — (where P 4 represents a polymerizable group; Sp 4 represents a spacer group and, when a plurality of Sp 4 groups are present, they may be identical to or different from one another; except for X 4 connected to N in the formula (G-1), X 4 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—, or —C≡C—; in case when X 4 is connected to N in the formula (G-1), X 4 represents a single bond; in case X 4 in the formula (G-2), X 4 represents a single bond, —O—, —S—, —CH 2 O—, —CO—, —COO—, —CO—S—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —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 —OCO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —CH═N—N═CH—, —CF═CF— or —C≡C—; and, when a plurality of X 4 groups are present, they may be identical to or different from one another (P 4 —(Sp 4 -X 4 ) k4 — does not include an —O—O— bond); and k4 represents an integer of 2 to 10),
wherein each of the polymerizable group of P 1 , P 2 and P 4 represents one of formulae (P-1) or (P-2),

2. The compound according to claim 1 , wherein Sp 1 , Sp 2 , and Sp 4 that are present in General Formula (I) each independently represent 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—, —CH═CH—, or —C≡C—.

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

4. A composition comprising the compound according to claim 1 .

5. A liquid crystal composition comprising the compound according to claim 1 .

6. A resin, a resin additive, an oil, a filter, a bonding agent, an adhesive, a fat, an ink, a drug, a cosmetic, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, an automotive component, an aircraft component, a machine component, an agricultural chemical, or a food that comprises the compound according to claim 1 , or a product including one or more selected from the resin, the resin additive, the oil, the filter, the bonding agent, the adhesive, the fat, the ink, the drug, the cosmetic, the detergent, the building material, the

Assignees

• Dainippon Ink & Chemicals

Inventors

• Kadomoto Yutaka
• Horiguchi Masahiro
• Koiso Akihiro

Classifications

• C07D277/82 Primary

  Nitrogen atoms · CPC title

• C09K19/3444

  the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine · CPC title

• C09K19/2014

  containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n- · CPC title

• C09K2019/0485

  Phenylene substituted in ortho position · CPC title

• C09K19/38

  Polymers · CPC title