Polymerizable compound having lateral substituent in terminal ring structure

Patent metadata

Field	Value
Publication number	US-9688787-B2
Application number	US-201514826630-A
Country	US
Kind code	B2
Filing date	Aug 14, 2015
Priority date	Apr 18, 2011
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

An object of the invention is to provide a polymerizable compound having small refractive index anisotropy and having high storage stability and high alignment properties when constituting a polymerizable liquid crystal composition, and provide a polymerizable liquid crystal composition containing the polymerizable compound. Further, the object is to provide a polymer produced by polymerizing the polymerizable liquid crystal composition and an optically anisotropic body including the polymer. The present invention provides a polymerizable compound represented by general formula (I), a polymerizable liquid crystal composition containing the compound as a constituent component, and further provides a polymer produced by polymerizing the polymerizable liquid crystal composition and an optically anisotropic body including the polymer.

First claim

The invention claimed is:

1. A polymerizable compound represented by general formula (I),

wherein P represents a substituent selected from polymerizable groups represented by formulae (P-1) to (P-15) below,

S 1 represents an alkylene group having 1 to 20 carbon atoms, in which one —CH 2 — or unadjacent two or more —CH 2 — may be each independently substituted by —O—, or a single bond, and when a plurality of S 1 is present, S 1 may be the same or different; 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 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF 2 CF 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—, —CY 1 ═CY 2 —, —C≡C—, or a single bond, wherein Y 1 and Y 2 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, or a cyano group, and when a plurality of X 1 is present, X 1 may be the same or different; n represents 0, 1, 2, 3, or 4; A 1 and A 2 each independently represent a 1,4-phenylene group, a naphthalene-2,6-diyl group, a 1,4-cyclohexylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a decahydronaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a pyridine-2,6-diyl group, a pyrimidine-2,5-diyl group, or a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted by a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkanoyl group having 1 to 7 carbon atoms; at least one hydrogen atom of the alkyl group, the alkoxy group, or the alkanoyl group may be substituted by a fluorine atom or chlorine atom, and when a plurality of A 1 is present, A 1 may be the same or different; A 3 represents a group selected from groups represented by formula (A 3 -1) to formula (A 3 -8) below,

wherein L 1 represents an alkyl group having 1 to 7 carbon atoms, in which at least one hydrogen atom may be substituted by a fluorine atom or a chlorine atom, one —CH═ or unadjacent two —CH═ in a group represented by the formula (A 3 -1) may be substituted by —N═, one —CH 2 — or unadjacent two —CH 2 — in groups represented by the formula (A 3 -2) and formula (A 3 -3) may be substituted by —O— or —S—, groups represented by the formula (A 3 -1) to the formula (A 3 -8) may be further substituted by a fluorine atom, a chlorine atom, a cyano group, a nitro group, or an alkyl group, alkoxy group, or alkanoyl group having 1 to 7 carbon atoms, in which at least one hydrogen atom may be substituted by a fluorine atom or chlorine atom; Z 1 and Z 2 each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF 2 CF 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 —, —COO—CH 2 —, —CH 2 —COO—, CH 2 —OCO—, —CY 3 ═CY 4 —, or a single bond wherein Y 3 and Y 4 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, or a cyano group, and when a plurality of Z 1 is present, Z 1 may be the same or different; R 1 represents a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having 1 to 12 carbon atoms, at least one hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom, or a cyano group; and m represents 0, 1, 2, 3, or 4,
wherein a polymer obtained by polymerizing the polymerizable compound has a haze value of 1.1 to 1.5.

2. The polymerizable compound according to claim 1 , wherein in the general formula (1), A 3 is represented by the formula (A 3 -1) or the formula (A 3 -5) in which L 1 represents a fluorine atom, a chlorine atom, or an alkyl group or alkoxy having 1 to 4 carbon atoms, and a hydrogen atom on a benzene ring or naphthalene ring may be substituted by a fluorine atom, a chlorine atom, or an alkyl group or alkoxy group having 1 to 4 carbon atoms.

3. The polymerizable compound according to claim 1 , wherein in the general formula (1), A 3 is represented by the formula (A 3 -1) or the formula (A 3 -5) in which L 1 represents a fluorine atom, a chlorine atom, a CH 3 group, or a CH 3 O group, and a hydrogen atom on a benzene ring or naphthalene ring may be substituted by a fluorine atom, a chlorine atom, a CH 3 group, or a CH 3 O group.

4. The polymerizable compound according to claim 1 , wherein in the general formula (1), Z 1 and Z 2 each independently represent —COO—, —OCO—, —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—, or —CH 2 —OCO—.

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

6. A polymer produced by polymerizing the polymerizable liquid crystal composition according to claim 5 .

7. The optically anisotropic body comprising the polymer according to claim 6 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Kusumoto Tetsuo
• Horiguchi Masahiro
• Matsumoto Takashi
• Aoki Yoshio
• Hayashi Masanao
• Iwakubo Masayuki

Classifications

• C07C69/78

  Benzoic acid esters · CPC title

• C09K2019/3416

  the heterocyclic ring being a four-membered ring, e.g. oxetane · CPC title

• C08F22/20 Primary

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• C09K2019/325

  containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin) · CPC title

• C07C69/92

  with etherified hydroxyl groups · CPC title