POLYMERIZABLE COMPOUND AND OPTICALLY ANISOTROPIC BODY

Abstract

A problem of the present invention is to provide a polymerizable compound and a polymerizable composition which cause little decrease in retardation and discoloration when a film-shaped polymer produced by polymerization is irradiated with ultraviolet/visible light for a long time at high temperature. A further problem is to provide a polymer produced by polymerizing the polymerizable composition and an optically anisotropic body using the polymer. As a result, a compound useful as a component of a polymerizable composition was obtained. An optically anisotropic body using a polymerizable liquid crystal composition containing the compound of the present invention is useful for application to an optical film and the like.

Claims

1. A polymerizable liquid crystal compound, wherein when aligned on a horizontally-aligned substrate, an absorption maximum wavelength λomax in an in-plane direction perpendicular to an alignment direction lies at 320 nm to 420 nm.

2. The compound according to claim 1, wherein when aligned on a horizontally-aligned substrate, at the wavelength λomax, absorbance Ae in the direction parallel to the alignment direction and absorbance Ao in the in-plane direction perpendicular to the alignment direction satisfy a formula (Formula I) below.
Ao/Ae>1   (Formula I)

3. The compound according to claim 1, represented by general formula (I),
P.sup.1—S.sup.1—X.sup.1.sub.kA.sup.11-Z.sup.11.sub.m1M.sup.1Z.sup.12-A.sup.12.sub.m2R.sup.1   (I) (in the formula, P.sup.1 represents a polymerizable group; S.sup.1 represents a spacer group or a single bond, and when a plurality of S.sup.1 are present, they may be the same or different; X.sup.1 represents —O—, —S—, —OCH.sub.2—, —CH.sub.2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH.sub.2—, —CH.sub.2S—, —CF.sub.2O—, —OCF.sub.2—, —CF.sub.2S—, —SCF.sub.2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH.sub.2CH.sub.2—, —OCO—CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2—COO—, —CH.sub.2CH.sub.2—OCO—, —COO—CH.sub.2—, —OCO—CH2—, —CH.sub.2—COO—, —CH.sub.2—OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and when a plurality of X are present, they may be the same or different (wherein P.sup.1—(S.sup.1—X.sup.1).sub.k— does not contain an —O—O— bond); A.sup.11 and A.sup.12 each independently represent a 1,4-phenylene group, a 1,4-cyelohexylene group, a pyridine-2,5-diyl group, a pyrmidine-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, which may be unsubstituted or substituted by one or more L, and when a plurality of A.sup.11 and/or A.sup.12 are present, they may be the same or different; Z.sup.11 and Z.sup.12 each independently represent —O—, —S—, —OCH.sub.2—, —CH.sub.2O—, —CH.sub.2CH.sub.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.sub.2—, —CH.sub.2S—, —CF.sub.2O—, —OCF.sub.2—, —CF.sub.2S—, —SCF.sub.2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH.sub.2CH.sub.2—, —OCO—CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2—COO—, —CH.sub.2CH.sub.2—OCO—, —COO—CH.sub.2—, —OCO—CH.sub.2—, —CH.sub.2—COO—, —CH.sub.2—OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and when a plurality of Z.sup.11 and/or Z.sup.12 are present are present, they may be the same or different; R.sup.1 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, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH.sub.2— or two or more unadjacent —CH.sub.2— may be each independently substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, or —C≡C—, and any hydrogen atom in the alkyl group may be substituted by a fluorine atom, or R.sup.1 may represent a group represented by —(X.sup.R—S.sup.R).sub.kR—P.sup.R (wherein P.sup.R represents a polymerizable group; S.sup.R represents a spacer group or a single bond, and when a plurality of S.sup.R are present, they may be the same or different; X.sup.R represents —O—, —S—, —OCH.sub.2—, —CH.sub.2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH.sub.2—, —CH.sub.2S—, —CF.sub.2O—, —OCF.sub.2—, —CF.sub.2S—, —SCF.sub.2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH.sub.2CH.sub.2—, —OCO—CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2—COO—, —CH.sub.2CH.sub.2—OCO—, —COO—CH.sub.2—, —OCO—CH.sub.2—, —CH.sub.2—COO—, —CH.sub.2—OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and when a plurality of X.sup.R are present, they may be the same or different (wherein —(X.sup.R—S.sup.R).sub.kR—P.sup.R does not contain an —O—O— bond): and kR represents an integer of 0 to 8); M.sup.1 represents a divalent hydrocarbon group containing a conjugated system; 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 mereapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimetliylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH.sub.2— or two or more unadjacent —CH.sub.2— may be each independently substituted by —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 when a plurality of L are present, they may be the same or different, and any hydrogen atom in the alkyl group may be substituted by a fluorine atom, or L may represent a group represented by —(X.sup.L—S.sup.L).sub.kL—P.sup.L (wherein P.sup.L represents a polymerizable group; S.sup.L represents a spacer group or a single bond, and when a plurality of S are present, they may be the same or different; X.sup.L represents —O—, —S—, —OCH.sub.2—, —CH.sub.2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH.sub.2—, —CH.sub.2S—, —CF.sub.2O—, —OCF.sub.2—, —CF.sub.2S—, —SCF.sub.2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH.sub.2CH.sub.2—, —OCO—CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2—COO—, —CH.sub.2CH.sub.2—OCO—, —COO—CH.sub.2—, —OCO—CH.sub.2—, —CH.sub.2—COO—, —CH.sub.2—OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and when a plurality of X are present, they may be the same or different (wherein —(X.sup.L—S.sup.L).sub.kL—P.sup.L does not contain an —O—O— bond); and kL represents an integer of 0 to 8); k represents an integer of 0 to 8; m1 and m2 each independently represent an integer of 0 to 5, and m1+m2 represents an integer of 1 to 5).

4. The compound according to claim 3, wherein in the general formula (I), P.sup.1 represents a group selected from formula (P-1) to formula (P-20) below. ##STR00082## ##STR00083##

5. The compound according to claim 3, wherein in the general formula (I), S.sup.1 each independently represent an alkylene group having 1 to 20 carbon atoms in which one —CH.sub.2— or two or more unadjacent —CH.sub.2— may be each independently substituted by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—.

6. The compound according to claim 3, wherein in the general formula (I), the total number of π electrons contained in M.sup.1 is 4 to 50.

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

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

9. A polymer produced by polymerizing the composition according to claim 7.

10. An optically anisotropic body comprising the polymer according to claim 9.

11. The optically anisotropic body according to claim 10, wherein when aligned on a horizontally-aligned substrate, an absorption maximum wavelength λomax in an in-plane direction perpendicular to an alignment direction lies at 320 nm to 420 nm.

12. The optically anisotropic body according to claim 10, wherein when aligned on a horizontally-aligned substrate, at the wavelength λomax, absorbance Ae in the direction parallel to the alignment direction and absorbance Ao in the in-plane direction perpendicular to the alignment direction satisfy a formula (Formula I) below.
Ao/Ae>1   (Formula I)

13. A resin, a resin additive, an oil, a filter, an adhesive, a pressure-sensitive adhesive, oil and fat, an ink, a medical product, 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, a display element, an electronic device, a communication device, an automobile component, an aircraft component, a machine component, an agricultural chemical or food, or a product using the same, which uses the compound according to claim 1.

Description

BRIEF DESCRIPTION OF DRAWINGS

[0252] [FIG. 1] an arrangement of a film to be evaluated and a polarization plate, (a): a state in which the alignment direction of a film to be evaluated is parallel to the polarization direction of a polarization plate, (b): a state in which the alignment direction of a film to be evaluated is perpendicular to the polarization direction of a polarization plate, 1: polarization plate (an arrow represents the polarization direction of a polarization plate), 2: a film to be evaluated (an arrow represents the alignment direction), I.sub.0: incident light, I: transmitted light