Polymerizable compound and optically anisotropic body

Patent metadata

Field	Value
Publication number	US-10919870-B2
Application number	US-201515772981-A
Country	US
Kind code	B2
Filing date	Nov 9, 2015
Priority date	Nov 9, 2015
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

There is provided a polymerizable composition, by which discoloration or alignment defects are less likely to occur when a filmy polymer, which is obtained by adding a polymerizable compound to the polymerizable composition and polymerizing this composition, is irradiated with ultraviolet light. There are also provided a polymer obtained by polymerizing the polymerizable composition, and an optically anisotropic body using the polymer. The present invention provides a polymerizable low-wavelength dispersive or polymerizable reverse-wavelength dispersive compound having a partial structure represented by Formula (Z-0). Further, the present invention provides a composition containing the compound; a polymer obtained by polymerizing the composition; and an optically anisotropic body obtained by using the polymer.

First claim

The invention claimed is:

1. A polymerizable low-wavelength dispersive or polymerizable reverse-wavelength dispersive compound,
wherein the polymerizable low-wavelength dispersive or polymerizable reverse-wavelength dispersive compound is a compound represented by Formula (I) below,
R 1 A 1 -z 1 m1 G 1 z 2 -A 2 m2 R 2   (I)

(in the formula, R 1 is represented by Formula (I-0-R) below,
P 0 Sp 0 -X 0 k0   (I-0-R)

(in the formula, P 0 represents a polymerizable group, Sp 0 represents a spacer group or a single bond, and if a plurality of Sp 0 's exist, they may be different from or identical to each other; X 0 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 a single bond, and if a plurality of X 0 's exist, they may be different from or identical to each other (provided that, P 0 -(Sp 0 -X 0 )k0-does not contain a —O—O— bond); and k0 represents an integer of 0 to 10),
R 2 represents a hydrogen atom, a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may be each independently substituted with —O—, —COO—, —OCO—, or —O—CO—O—,
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 these groups may be unsubstituted or may be substituted with one or more of substituent groups L, 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, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and if a plurality of L's exist in the compound, they may be different from or identical to each other;
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—, a single bond, or a group represented by —CR 0-1 R 0-2 O— or OCR 0-1 R 0-2 —(in the formulas, R 0-1 and R 0-2 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 —'s 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 any hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom; and two terminal groups in —CR 0-1 R 0-2 O— are connected to ring structures), if a plurality of Z 1 's exist, they may be different from or identical to each other, if a plurality of Z 2 's exist, they may be different from or identical to each other, and at least one of Z 1 and Z 2 represents a group represented by —CR 0-1 R 0-2 O— or —OCR 0-1 R 0-2 —;
G 1 represents a divalent group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings, the number of π electrons contained in the aromatic ring of the group represented by G 1 is 12 or more, and the group represented by G 1 may be unsubstituted or may be substituted with one or more of substituent groups L G ;
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, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and if a plurality of L G 's exist in the compound, they may be different from or identical to each other; and
m1 and m2 each independently represent an integer of 0 to 6, and m1+m2 represents an integer of 0 to 6).

2. The compound according to claim 1 ,
wherein P 0 in Formula (I-0-R) represents a group selected from Formulae (P-1) to (P-20) below:

3. The compound according to claim 1 ,
wherein Sp 0 's in Formula (I-0-R) each independently represent an alkylene group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may be each independently substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—.

4. The compound according to claim 1 ,
wherein G 1 in Formula (I) represents a group selected from Formulae (M-1) to (M-6) below:

(in the formulae, these groups may be unsubstituted or substituted with one or more of the aforementioned substituent groups L G , any —CH═'s may be each independently substituted with —N═, —CH 2 —'s may be each independently substituted with —O—, —S—, —NR T -(in the formula, R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS—, or —CO—, and T 1 represents a group selected from Formulae (T1-1) to (T1-6) below:

(in the formulae, each of these groups may have a bond at any position, any —CH═'s may be each independently substituted with —N═, —CH 2 —'s may be each independently substituted with —O—, —S—, —NR T -(in the formula, R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS—, or —CO—; and these groups may be unsubstituted or substituted with one or more of the aforementioned substituent groups L G )); or
a group selected from Formulae (M-7) to (M-14) below:

(in the formulae, these groups may be unsubstituted or substituted with one or more of the aforementioned substituent groups L G , any —CH═'s may be each independently substituted with —N═, —CH 2 —'s may be each independently substituted with —O—, —S—, —NR T -(in the formula, R T represents

Assignees

• Dainippon Ink & Chemicals

Inventors

• Horiguchi Masahiro
• Kadomoto Yutaka
• Koiso Akihiro
• Hayashi Masanao
• Saitou Yoshitaka
• Teng Yan
• Li Zhimin

Classifications

• C07C251/88

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

• C07C2602/40

  the bicyclo ring system containing six carbon atoms · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D339/06

  having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates · CPC title

• C07C2603/32

  Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes · CPC title