JPH0762337A - Liquid crystalline polymer photochromic material - Google Patents

Abstract

(57) [Summary] [Structure] At least the following formula (A): [In the formula, R ¹ represents hydrogen or a methyl group. X represents a substituent having a spirooxazine skeleton. ] And a monomer represented by the following formula (B): [In the formula, R ² represents hydrogen or a methyl group. Y represents a mesogen group. ] A liquid crystalline polymer photochromic material obtained by copolymerizing a monomer represented by [Effect] A liquid crystalline polymer photochromic material having sufficient durability can be provided.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal photochromic material, which is particularly useful for printing, optical equipment, information recording materials, display materials, light control materials, clothing, decorative materials, and light. It is preferably used as an element.

[0002]

2. Description of the Related Art Heretofore, some examples have been known as liquid crystal polymer photochromic materials. For example, Ange
wandte Chemie International
alEdition in English, Vol. 26 (No. 11), page 1178 (1987) and the same magazine 3.
Volume 0 (No. 1), page 76 (1991), shows an example of a liquid crystalline polymer photochromic material having a liquid crystal molecule and a photochromic molecule in the side chain of the polymer.

[0003]

However, the conventional liquid crystal polymer photochromic material has insufficient durability.

An object of the present invention is to provide a liquid crystalline polymer photochromic material having sufficient durability.

[0005]

In order to solve the above problems, the liquid crystalline polymer photochromic material of the present invention is
It has the following configuration.

"At least the following formula (A)

[Chemical 5] [In the formula, R ¹ represents hydrogen or a methyl group.

X represents a substituent having a spirooxazine skeleton. ] And the following formula (B)

[Chemical 6] [In the formula, R ² represents hydrogen or a methyl group.

Y represents a mesogenic group. ] A liquid crystalline polymer photochromic material obtained by copolymerizing a monomer represented by In the formula (A), R ¹ represents hydrogen or a methyl group.

X can be used without particular limitation as long as it is a substituent having a spirooxazine skeleton, and is preferably a compound represented by the following formula (C):

[Chemical 7] [In formula, (alpha) ring and (beta) ring represent a C5-C22 aromatic ring.

R ³ and R ⁴ represent a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms.

R ⁵ represents a substituent selected from an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms and Z ¹ .

R ^{6 to} R ¹² are hydrogen, hydroxyl group, alkoxy group having 1 to 20 carbon atoms, aralkoxy group having 7 to 15 carbon atoms, aryloxy group having 6 to 14 carbon atoms, and 1 carbon atom.
˜20 acyloxy group, C 1-20 alkyl group, C 7-15 aralkyl group, C 6-14 aryl group, halo group, carboxyl group, C 2-20
Alkoxycarbonyl group, C8-20 aralkoxycarbonyl group, C7-20 aryloxycarbonyl group, C1-20 carbamoyl group, C1
To carbamoyloxy group, C1 to C20 acyl group, C0 to C10 amino group, nitro group and Z ²
Represents a substituent selected from

Z ¹ is the following formula

[Chemical 8] {M represents an integer of 1 to 10. } Represents a divalent substituent selected from.

Z ² is the following formula

[Chemical 9] {N represents an integer of 1 to 10. } Represents a divalent substituent selected from.

One of R ^{6 to} R ¹² is Z ¹ or Z ^2.
Represents ] The substituent shown by these is used.

In the formula (C), the α ring and the β ring have 5 carbon atoms.
The aromatic ring represented by formula 22 is represented by the following formula.

[Chemical 10] The specific examples of the β ring are shown below.

[Chemical 11] The items shown in are listed.

R ³ and R ⁴ represent a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms. Specific examples thereof include a methyl group and an ethyl group. , Propyl group, hexyl group, octadecyl group, icosyl group, isopropyl group, tert-butyl group, 2
Examples thereof include an alkyl group such as an ethylhexyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group; and an aralkyl group such as a benzyl group, a phenethyl group, and a naphthylmethyl group.

R ⁵ represents a substituent selected from an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms and Z ² , and specific examples thereof include a methyl group,
Ethyl group, propyl group, hexyl group, octadecyl group,
Icosyl group, isopropyl group, tert-butyl group, 2-ethylhexyl group, cyclohexyl group, norbornyl group,
Examples thereof include an alkyl group such as an adamantyl group; an aralkyl group such as a benzyl group, a phenethyl group, and a naphthylmethyl group; Z ^{2 and the} like.

R ^{6 to} R ¹² are hydrogen, hydroxyl group, alkoxy group having 1 to 20 carbon atoms, aralkoxy group having 7 to 15 carbon atoms, aryloxy group having 6 to 14 carbon atoms, and 1 carbon atom.
˜20 acyloxy group, C 1-20 alkyl group, C 7-15 aralkyl group, C 6-14 aryl group, halo group, carboxyl group, C 2-20
Alkoxycarbonyl group, C8-20 aralkoxycarbonyl group, C7-20 aryloxycarbonyl group, C1-20 carbamoyl group, C1
To carbamoyloxy group, C1 to C20 acyl group, C0 to C10 amino group, nitro group and Z ²
And a specific example thereof is hydrogen; a hydroxyl group; a methoxy group, an ethoxy group,
Propoxy group, hexyloxy group, octadecyloxy group,
Alkoxy groups such as icosyloxy group, isopropoxy group, tert-butoxy group, vinyloxy group, allyloxy group and glycidyloxy group; aralkoxy groups such as benzyloxy group, phenethyloxy group and naphthylmethyloxy group;
Aryloxy groups such as phenoxy group and naphthyloxy group;
Formyloxy group, acetoxy group, propionyloxy group, valeryloxy group, hexanoyloxy group, lauroyloxy group, palmitoyloxy group, stearoyloxy group, cyclohexanecarbonyloxy group, benzoyloxy group, nicotinoyloxy group, anisoyloxy group, vera Acyloxy groups such as troyloxy group, naphthoyloxy group and (meth) acryloyloxy group; methyl group, ethyl group, propyl group, hexyl group, octyl group, octadecyl group, isopropyl group, tert-butyl group, 2-ethylhexyl group Group, vinyl group, allyl group, cyclopentyl group, cyclohexyl group, norbornyl group, adamantyl group and other alkyl groups; benzyl group, phenethyl group, naphthylmethyl group and other aralkyl groups; phenyl group, naphthyl group, etc. Group; halo group such as fluoro group, chloro group, bromo group, iodo group; carboxyl group; methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, hexyloxycarbonyl group, isopropoxycarbonyl group, vinyloxycarbonyl group, allyl Alkoxycarbonyl groups such as oxycarbonyl group, (2,2,6,6-tetramethyl-4-piperidyl) oxycarbonyl group and glycidyloxycarbonyl group; Aralkoxycarbonyl groups such as benzyloxycarbonyl group and phenethyloxycarbonyl group Group; aryloxycarbonyl group such as phenoxycarbonyl group and naphthyloxycarbonyl group; carbamoyl group, N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-hexylcarbamoyl group, -Carbamoyl group such as benzylcarbamoyl group and N-phenylcarbamoyl group; carbamoyloxy group, N-methylcarbamoyloxy group, N-ethylcarbamoyloxy group, N-propylcarbamoyloxy group, N-hexylcarbamoyloxy group, N-octadecyl group Carbamoyloxy group, N-isopropylcarbamoyloxy group,
N-benzylcarbamoyloxy group, N-phenylcarbamoyloxy group, N-naphthylcarbamoyloxy group, N-methacryloylcarbamoyloxy group, N-
(Methacryloyloxyethyl) carbamoyloxy group such as carbamoyloxy group; formyl group, acetyl group, propionyl group, acyl group such as (meth) acryloyl group; amino group, piperidino group, 1-pyrrolidyl group,
Examples thereof include amino groups such as morpholino group, dimethylamino group and diethylamino group; and nitro group.

A more preferred specific example of X is the following formula (D):

[Chemical 12] [In the formula, A ¹ represents a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms.

A ^{2 to} A ⁶ are hydrogen, hydroxyl group, alkoxy group having 1 to 20 carbon atoms, aralkoxy group having 7 to 15 carbon atoms, aryloxy group having 6 to 14 carbon atoms, and 1 carbon atom.
˜20 acyloxy group, C 1-20 alkyl group, C 7-15 aralkyl group, C 6-14 aryl group, halo group, carboxyl group, C 2-20
Alkoxycarbonyl group, C8-20 aralkoxycarbonyl group, C7-20 aryloxycarbonyl group, C1-20 carbamoyl group, C1
Represents a substituent selected from a carbamoyloxy group having 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an amino group having 0 to 10 carbon atoms, and a nitro group. ] And a substituent represented by the following formula (E)

[Chemical 13] [In the formula, A ⁷ represents a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms.

A ^{8 to} A ¹² are hydrogen, hydroxyl group, alkoxy group having 1 to 20 carbon atoms, aralkoxy group having 7 to 15 carbon atoms, aryloxy group having 6 to 14 carbon atoms, and 1 carbon atom.
˜20 acyloxy group, C 1-20 alkyl group, C 7-15 aralkyl group, C 6-14 aryl group, halo group, carboxyl group, C 2-20
Alkoxycarbonyl group, C8-20 aralkoxycarbonyl group, C7-20 aryloxycarbonyl group, C1-20 carbamoyl group, C1
Represents a substituent selected from a carbamoyloxy group having 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an amino group having 0 to 10 carbon atoms, and a nitro group. ] The substituent represented by these can be mentioned.

In the formulas (D) and (E), A ¹ and A ⁷
Is an alkyl group having 1 to 20 carbon atoms and 7 to 20 carbon atoms
Represents a substituent selected from the aralkyl groups of, and specific examples thereof include a methyl group, an ethyl group, a propyl group,
Alkyl groups such as hexyl group, octadecyl group, icosyl group, isopropyl group, tert-butyl group, 2-ethylhexyl group, cyclohexyl group, norbornyl group, adamantyl group; aralkyl groups such as benzyl group, phenethyl group, naphthylmethyl group, etc. Can be mentioned.

A ^{2 to} A ⁶ and A ^{8 to} A ¹² are hydrogen, hydroxyl group, alkoxy group having 1 to 20 carbon atoms, aralkoxy group having 7 to 15 carbon atoms, aryloxy group having 6 to 14 carbon atoms, and carbon number. 1-20 acyloxy groups, 1-carbon
An alkyl group having 20 carbon atoms, an aralkyl group having 7 to 15 carbon atoms, an aryl group having 6 to 14 carbon atoms, a halo group, a carboxyl group,
C2-C20 alkoxycarbonyl group, C8-
20 aralkoxycarbonyl group, C7-20 aryloxycarbonyl group, C1-20 carbamoyl group, C1-20 carbamoyloxy group, C1-20 acyl group, C0 10 represents a substituent selected from an amino group and a nitro group, and specific examples thereof include hydrogen; a hydroxyl group; a methoxy group, an ethoxy group, a propoxy group, a hexyloxy group, an octadecyloxy group, an icosyloxy group. , Alkoxy groups such as isopropoxy group, tert-butoxy group, vinyloxy group, allyloxy group and glycidyloxy group; aralkoxy groups such as benzyloxy group, phenethyloxy group, naphthylmethyloxy group; aryloxy groups such as phenoxy group and naphthyloxy group; formyl Oxy group, acetoxy group, propionyloxy group, valeryl Oxy group, hexanoyloxy group,
Lauroyloxy group, palmitoyloxy group, stearoyloxy group, cyclohexanecarbonyloxy group, benzoyloxy group, nicotinoyloxy group, anisoyloxy group, veratroyloxy group, naphthoyloxy group,
An acyloxy group such as a (meth) acryloyloxy group;
Methyl group, ethyl group, propyl group, hexyl group, octyl group, octadecyl group, isopropyl group, tert-butyl group, 2-ethylhexyl group, vinyl group, allyl group, cyclopentyl group, cyclohexyl group, norbornyl group, adamantyl group, etc. Alkyl group; aralkyl group such as benzyl group, phenethyl group, naphthylmethyl group; aryl group such as phenyl group, naphthyl group; halo group such as fluoro group, chloro group, bromo group, iodo group; carboxyl group; methoxycarbonyl group, Ethoxycarbonyl group, propoxycarbonyl group, hexyloxycarbonyl group, isopropoxycarbonyl group, vinyloxycarbonyl group, allyloxycarbonyl group, (2,2,6,6-tetramethyl-4-piperidyl) oxycarbonyl group, glycidyloxy Carboni Groups such as alkoxycarbonyl groups; benzyloxycarbonyl groups, phenethyloxycarbonyl groups and other aralkoxycarbonyl groups; phenoxycarbonyl groups, naphthyloxycarbonyl groups, and other aryloxycarbonyl groups; carbamoyl groups, N-methylcarbamoyl groups, N A carbamoyl group such as an ethylcarbamoyl group, an N-propylcarbamoyl group, an N-hexylcarbamoyl group, an N-benzylcarbamoyl group and an N-phenylcarbamoyl group; a carbamoyloxy group, an N-methylcarbamoyloxy group, an N-ethylcarbamoyloxy group , N-propylcarbamoyloxy group, N-hexylcarbamoyloxy group, N-octadecylcarbamoyloxy group, N-isopropylcarbamoyloxy group,
N-benzylcarbamoyloxy group, N-phenylcarbamoyloxy group, N-naphthylcarbamoyloxy group, N-methacryloylcarbamoyloxy group, N-
(Methacryloyloxyethyl) carbamoyloxy group such as carbamoyloxy group; formyl group, acetyl group, propionyl group, acyl group such as (meth) acryloyl group; amino group, piperidino group, 1-pyrrolidyl group,
Examples thereof include amino groups such as morpholino group, dimethylamino group and diethylamino group; and nitro group.

In the formula (B), R ² represents hydrogen or a methyl group.

Y represents a mesogenic group, and the mesogenic group can be used without particular limitation as long as it is a substituent capable of imparting liquid crystallinity to the material. Specific examples include the following formulas.

[Chemical 14] [Wherein W ¹ and W ² are respectively the following formulas:

[Chemical 15] Represents a substituent selected from

R ²⁰ is an alkoxy group, an aralkoxy group,
Aryloxy group, halo group, cyano group, carboxyl group,
Alkoxycarbonyl group, aralkoxycarbonyl group,
It represents a substituent selected from an aryloxycarbonyl group and an alkyl group.

K represents an integer of 1 to 5. When k is 2 or more, each R ²⁰ may be the same or different. ] The substituent shown by these can be mentioned.

The liquid crystalline polymer photochromic material of the present invention may be in any of copolymerization forms such as random, block, graft and alternating.

The random copolymer can be obtained by polymerizing in the presence of each of the copolymerizable monomers and the polymerization initiator using a conventional radical polymerization method. in this case,
As the polymerization initiator, an azo initiator is preferably used from the viewpoint of preventing modification and deterioration of the photochromic compound portion.

In addition to this, polymer photochromic materials having various copolymerization forms can be obtained by using known polymerization methods such as ionic polymerization, photopolymerization, radiation polymerization and iniferter polymerization.

In the liquid crystalline polymer photochromic material of the present invention, the content of the monomer of the general formula (A) is preferably 0.1% by weight to 50% by weight as a monomer unit, more preferably 1% by weight. Is about 20% by weight. When the content of the monomer of the general formula (A) is less than 0.1% by weight, it is difficult to obtain sufficient photochromic properties, and when it is more than 50% by weight, the liquid crystallinity tends to decrease.

The molecular weight of the liquid crystalline polymer photochromic material of the present invention is 1,000 to 1,000 in terms of weight average molecular weight.
The range of 50,000 is preferable, and the range of 5,000 to 100,000 is more preferable from the viewpoint of film-forming property as a polymer.

The liquid crystalline polymer photochromic material of the present invention may have a monomer other than the monomer of the general formula (A) and the monomer of the general formula (B) as a copolymerization component. The monomer in that case may be a compound having a polymerizable substituent, and may be a compound having two or more polymerizable substituents in one molecule. Specific examples thereof include acrylic acid. Acrylic monomers such as acid, methacrylic acid, acrylic acid ester, methacrylic acid ester, acrylic acid amide, methacrylic acid amide, acrylonitrile, methacrylonitrile, ethylene glycol dimethacrylate; styrene, divinylbenzene,
Styrene-based monomers such as α-methylstyrene; vinyl acetate-based monomers; olefin-based monomers such as ethylene, propylene, butadiene, vinyl chloride, and vinylidene chloride; silane-based compounds having organic polymerizable functional groups; organic polymerizable functional groups Spirooxazine compounds having; spiropyran compounds having organic polymerizable functional groups; diarylethene compounds having organic polymerizable functional groups; fulgide compounds having organic polymerizable functional groups; chromene compounds having organic polymerizable functional groups, etc. Is mentioned.

The liquid crystalline polymer photochromic material of the present invention can be formed on a part or all of various substrates by applying a coating method or various printing methods. As the coating method, various methods such as a dip coating method, a spin coating method, a roll coating method and a bar coating method can be adopted.

Further, the liquid crystal polymer photochromic material of the present invention can be used as a bulk molding or as a film.

From the viewpoint of improving the repeated durability of the liquid crystalline photochromic material of the present invention, it is particularly effective to block oxygen and water during use. Further, known additives for the purpose of improving durability, for example, singlet oxygen quencher typified by nickel salt, nitroxy radical compound, antioxidant represented by hindered amine compound or polymer thereof, ultraviolet absorber, A triplet quencher or the like can be used.

Applications of the liquid crystalline polymer photochromic material of the present invention include inks, printed materials, sunglasses lenses, various goggles, protective eyeglass lenses, camera light control filters, helmet shields, information recording materials, displays,
Display materials that can be repeatedly erased, windshields, automobile windows such as sunroofs, curtains, window blinds, light control film, light control laminated glass, change in light intensity, refractive index, electrical resistance, light transmittance, Optical elements that convert to changes in absorbance, clothes, toys, cosmetics,
A suitable example is a writing instrument. In particular, the liquid crystalline polymer photochromic material of the present invention is preferably used as an information recording material that is rewritable and has excellent thermal stability of information.

[0039]

EXAMPLES The present invention will now be described with reference to examples, but the present invention is not limited thereto. Synthesis Example 1 [1] 2,3,3-Trimethyl-5-methoxyindolenine (51 g) and methyl iodide (213 g)
Was reacted at reflux temperature for 12 hours. After the reaction, the produced solid was washed with acetone to obtain 1,2,3,3-tetramethyl-5-methoxyindolenium iodide. Next, this 1,2,3,3-tetramethyl-5-methoxyindolenium iodide (27 g) was added to 400
It was suspended in ml of methylene chloride, and ice-cooled with stirring. A solution of boron tribromide (21 g) in methylene chloride (50 ml) was added dropwise to this suspension over 1 hour. Then, the temperature of the reaction solution was raised to room temperature, and stirring was continued at room temperature for 3 days. Next, water (300
ml), and the mixture is stirred for 30 minutes, 2M aqueous sodium hydroxide solution (100 ml) is further added, and the mixture is stirred at 50 ° C. for 1 hour.
Stir for hours. After that, 1 M hydrochloric acid was added to neutralize the liquid, and then extraction was performed with ethyl acetate. Anhydrous sodium sulfate was added to the extract to remove water. After removing sodium sulfate by filtration, ethyl acetate was distilled off to obtain 1,3,3-trimethyl-2-methylene-5-hydroxyindoline.

[2] 1,3,3-Trimethyl-2-methylene-5-hydroxyindoline (2.9 g) and 1-nitroso-2-naphthol (1.9 g) in anhydrous ethanol (35 ml) at reflux temperature. And reacted for 9 hours.
Next, the solvent is distilled off from the reaction mixture, and then the product is separated and purified by silica gel column chromatography (developing solvent; ethyl acetate / hexane mixed solvent) to give the compound of formula (1)

[Chemical 16] A crystal of the compound of was obtained.

[3] the compound of the formula (1) (3.0 g),
Triethylamine (6.6 g) and methylene chloride (8
(0 ml) was stirred at room temperature, and a solution of methacrylic acid chloride (3.6 g) and methylene chloride (20 ml) was added dropwise over 20 minutes. After the dropping was completed, stirring was continued for another 30 minutes.
After completion of the reaction, the solvent was distilled off, and the residue was purified by silica gel column chromatography (developing solvent; ethyl acetate / hexane mixed solvent) to give the compound of formula (2).

[Chemical 17] Was obtained.

Synthesis Example 2 [1] 1,3,3-Trimethyl-2-methyleneindoline (9.2 g) and 1-nitroso-2,7-dihydroxynaphthalene (10 g) were mixed with absolute ethanol (100 g).
ml) at reflux temperature for 3 hours. Next, the solvent was distilled off from the reaction mixture, followed by separation and purification by silica gel column chromatography (developing solvent; ethyl acetate / hexane mixed solvent) to give a compound of formula (3)

[Chemical 18] A crystal of the compound of was obtained.

[3] The compound of the formula (3) (1.5 g),
Triethylamine (4.0 g) and methylene chloride (5
(0 ml) was stirred at room temperature, and a solution of methacrylic acid chloride (1.0 g) and methylene chloride (10 ml) was added dropwise over 20 minutes. After the dropping was completed, stirring was continued for another 30 minutes.
After completion of the reaction, the solvent was distilled off, followed by separation and purification by silica gel column chromatography (developing solvent; ethyl acetate / hexane mixed solvent) to give a compound of formula (4)

[Chemical 19] Was obtained.

Example 1 The following formula (5)

[Chemical 20] And a compound of formula (2) (0.1 g) obtained in Synthesis Example 1 with tetrahydrofuran (3 g).
ml), and azobisisobutyronitrile (4 mg) was added as a polymerization initiator, followed by polymerization at reflux temperature for 24 hours in a nitrogen atmosphere. After completion of the polymerization, reprecipitation and purification were carried out three times using ethanol, and then dried to obtain a liquid crystal polymer photochromic material. The liquid crystalline photochromic material exhibited an interference color peculiar to liquid crystals at a temperature of 70 ° C. when observed under a polarizing microscope.

Example 2 The following formula (6)

[Chemical 21] (1.0 g), a compound of formula (4) (0.05 g) obtained in Synthesis Example 2, tetrahydrofuran (3 ml) and azobisisobutyronitrile (2 m
g) was placed in a glass ampoule, oxygen was removed by freeze deaeration, and then the ampoule was sealed. Polymerization was carried out at 80 ° C. for 24 hours. The solution was taken out from the ampoule, reprecipitated and purified using ethanol three times, and then dried to obtain a liquid crystalline polymer photochromic material. The liquid crystalline photochromic copolymer showed an interference color peculiar to liquid crystals at a temperature of 70 ° C. when observed under a polarizing microscope.

Claims (3)

[Claims] 1. At least the following formula (A): [In the formula, R ¹ represents hydrogen or a methyl group. X represents a substituent having a spirooxazine skeleton. ] And a monomer represented by the following formula (B): [In the formula, R ² represents hydrogen or a methyl group. Y represents a mesogen group. ] A liquid crystalline polymer photochromic material obtained by copolymerizing a monomer represented by 2. X is the following formula (D): [In the formula, A ¹ represents a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms. A ^{2 to} A ⁶ are hydrogen, a hydroxyl group, and a carbon number of 1 to
20 alkoxy group, C 7-15 aralkoxy group, C 6-14 aryloxy group, C 1-20
Acyloxy group, C1-20 alkyl group, C7-15 aralkyl group, C6-14 aryl group, halo group, carboxyl group, C2-20 alkoxycarbonyl group, C8 To aralkoxycarbonyl group, C7 to C20 aryloxycarbonyl group, C1 to C20 carbamoyl group, and C1 to C20
A carbamoyloxy group, an acyl group having 1 to 20 carbon atoms,
It represents a substituent selected from an amino group and a nitro group having 0 to 10 carbon atoms. ] Or a substituent represented by the following formula (E): [In the formula, A ⁷ represents a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms. A ^{8 to} A ¹² are hydrogen, a hydroxyl group, and 1 to ¹² carbon atoms.
20 alkoxy group, C 7-15 aralkoxy group, C 6-14 aryloxy group, C 1-20
Acyloxy group, C1-20 alkyl group, C7-15 aralkyl group, C6-14 aryl group, halo group, carboxyl group, C2-20 alkoxycarbonyl group, C8 To aralkoxycarbonyl group, C7 to C20 aryloxycarbonyl group, C1 to C20 carbamoyl group, and C1 to C20
A carbamoyloxy group, an acyl group having 1 to 20 carbon atoms,
It represents a substituent selected from an amino group and a nitro group having 0 to 10 carbon atoms. ] The liquid crystal polymer photochromic material according to claim 1, which is a substituent represented by the following formula. 3. An information recording material comprising the liquid crystalline polymer photochromic material according to claim 1.