JP3384086B2 - Photochromic optical recording material - Google Patents

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a photochromic optical recording material containing an ethylene derivative into which a substituent having a π-conjugated chain is introduced.

[0002]

2. Description of the Related Art A photochromic material is a material containing a molecule or a molecular assembly which reversibly produces two isomers having different states by the action of light. When using a photochromic material as an optical recording medium, various performances are required, one of which is long wavelength sensitivity. That is, since the light source used for optical recording is a semiconductor laser, it is required to have sensitivity in the semiconductor laser region (650 to 850 nm).

[0003]

However, most of the conventionally proposed photochromic molecules do not have long-wavelength region sensitivity, and those having long-wavelength region sensitivity have poor thermal stability or low sensitivity. Had a drawback such as.

Two methods can be considered for imparting long-wavelength region sensitivity to the photochromic material. One is to introduce an intramolecular charge transfer functional group, and the other is to introduce a long π-conjugated chain into the molecule.

As the former method, it has been attempted to introduce a strong electron donating group and an electron accepting group into the same molecule,
A diarylethene molecule having a sensitivity at a wavelength of 828 nm has been reported (SLGilat, SHKawai, JM.Lehn, Chem.
Commun. 1439 (1993)). However, the ring-closed body of this molecule is thermally unstable and has the drawback of returning to the original ring-opened body in the dark, and cannot be used as an optical recording medium.

On the other hand, the present inventors have found that the latter having a long π-conjugated chain in a molecule is effective in having sensitivity in a long wavelength region without impairing thermal stability. Found.

The present invention has been made in view of the above conventional circumstances, and an object of the present invention is to provide a photochromic optical recording material which is thermally stable and has long-range sensitivity.

[0008]

The photochromic optical recording material according to claim 1 contains an ethylene derivative in which a substituent having a π-conjugated chain is introduced into the carbon at the 1-position and the carbon at the 2-position of the ethylene bond. A photochromic optical recording material, wherein the π-conjugated chain is a hetero 5-membered ring chain, and at least one of the substituent at the 1-position carbon and the substituent at the 2-position carbon is hetero 5. It is characterized by having two or more member rings.

The photochromic optical recording material of claim 2 is the same as the photochromic optical recording material of claim 1.
The hetero 5-membered ring is optionally substituted pyrrole, thiophene, furan, selenophene or benzo (c) thiophene.

A photochromic optical recording material according to a third aspect is the photochromic optical recording material according to the first or second aspect, wherein the ethylene derivative is represented by the following general formula [I].

[0011]

[Chemical 2]

(In the formula, ring A represents a perfluorocycloalkyl group, an acid anhydride or an optionally substituted maleimide group, and R ¹ and R ² are an alkyl group, an alkoxy group, a halogen atom or a dialkylamino group. or it represents a trifluoromethyl ^{group, R 3, R 4, R} 5, R 6, R 7, R
⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a trifluoromethyl group, a cyano group, a nitro group, a dialkylamino group or an aryl group which may be substituted. , M and n are 1 to 5
Represents However, at least one of m and n represents 2 or more. The present invention will be described in detail below.

In the present invention, the π-conjugated chain formed in the ethylene-based derivative constituting the photochromic optical recording material is a plurality of 5-membered heterocyclic rings such as pyrrole, thiophene, furan, selenophene or benzo (c) thiophene. It is composed of a 5-membered heterocyclic chain. That is, in the present invention, a substituent having a π-conjugated chain introduced at the 1-position carbon and the 2-position carbon of the ethylene bond of the ethylene derivative (hereinafter, may be referred to as “π-conjugated substituent”).
Is a poly-hetero 5-membered ring group in which one hetero 5-membered ring group or two or more hetero 5-membered rings are linked. However, at least one of the π-conjugated substituents bonded to the ethylene bond of the ethylene derivative is a polyhetero 5-membered ring group in which two or more hetero 5-membered rings are linked. The hetero 5-membered ring chain formed of such a substituent constitutes a very preferable π-conjugated chain from the viewpoint of oxidation resistance and flexibility of the obtained photochromic optical recording material.

The length of the 5-membered heterocyclic ring constituting the π-conjugated chain, that is, the number of linked 5-membered heterocyclic rings can be freely controlled, but in view of easiness of synthesis and reactivity. Each π
1 or 2 to 5 as the number of hetero 5-membered rings of the conjugated substituent,
That is, 3 to 10 as the number of hetero 5-membered rings constituting the π-conjugated chain
It is desirable to make it individual.

A long π consisting of such a 5-membered heterocyclic chain
-By introducing a conjugated chain into the ethylene derivative, a closed ring of the ethylene derivative forms a π-conjugated system spread over the entire molecule, the absorption wavelength shifts to the long wavelength side, and the sensitivity to the semiconductor laser is increased. To have.

In the present invention, the type and number of the hetero 5-membered ring of the π-conjugated substituent introduced at the 1-position carbon of the ethylene derivative and the hetero 5 of the π-conjugated substituent introduced at the 2-position carbon. The type and number of member rings may be the same or different, but as described above, the number of hetero 5-membered rings of at least one π-conjugated substituent is 2 or more.

In the present invention, the π-conjugated substituent preferably includes those represented by the following formulas (1) to (6).

[0018]

[Chemical 3]

Here, R ¹¹ and R ¹⁴ are an alkyl group having 1 to 8 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group and a tert-butyl group; a methoxy group. , Ethoxy group, n-propoxy group, is
an alkoxy group having 1 to 6 carbon atoms such as an o-propoxy group and an n-butoxy group; a dialkylamino group such as a dimethylamino group and a diethylamino group; R ¹² is a hydrogen atom; a methyl group, an ethyl group, an n-propyl group , An iso-propyl group,
an alkyl group having 1 to 6 carbon atoms such as n-butyl group and tert-butyl group; an alkoxy group having 1 to 6 carbon atoms such as methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, and n-butoxy group A dialkylamino group such as a dimethylamino group and a diethylamino group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a cyano group; a nitro group; or a lower alkyl group, a lower alkoxy group, a lower alkylamino group, a lower Dialkylamino group,
6 carbon atoms such as phenyl group, tolyl group and naphthyl group which may be substituted with amino group, halogen atom, cyano group, etc.
Represents an aryl group of -12.

R ¹³ and R ¹⁵ are the same as R ¹² or represent a hetero 5-membered ring system π-conjugated chain represented by the following general formulas (7) to (15).

[0021]

[Chemical 4]

R ¹² and R ¹³ are connected to each other to form a carbon ring such as an alkylene ring having 3 to 5 carbon atoms, a benzene ring, a naphthalene ring or a pyridine ring, a pyrazine ring, a pyrimidine ring,
Heterocycles such as a pyridazine ring, a pyran ring, a furan ring and a thiophene ring may be formed.

R ¹⁶ is a hydrogen atom, or a methyl group, an ethyl group, or an n-group, each of which may have a substituent such as a halogen atom, a lower alkoxy group, a hydroxyl group, a cyano group, an amino group or a nitro group. Carbon number 1 such as propyl group, iso-propyl group, n-butyl group, tert-butyl group
An alkyl group having 6 to 6; an aryl group having 6 to 12 carbon atoms such as phenyl group, tolyl group and naphthyl group; or a cycloalkyl group having 3 to 8 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group. Represent

When R ¹² and R ^{13 shown above} are linked to form a carbocycle or a heterocycle, specifically, they are a benzofuran ring, a benzothiophene ring, an indole ring, a benzoxazole ring, a benzothiazole ring. When forming an indazole ring or the like, the ring may have one or more substituents. Examples of such a substituent include a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; a hydroxyl group;
C1-C6 alkyl groups such as methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group; methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group. An alkoxy group having 1 to 6 carbon atoms such as a group; a cyano group; a nitro group; a methoxycarbonyl group,
Ethoxycarbonyl group, n-propoxycarbonyl group,
C2-C7 alkoxycarbonyl group such as iso-propoxycarbonyl group; C1-C6 haloalkyl group such as trifluoromethyl group; C6-C12 aryl group such as phenyl group, tolyl group and naphthyl group A cycloalkyl group having 3 to 8 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; aryloxycarbonyl group having 7 to 13 carbon atoms such as phenoxycarbonyl group, naphthyloxycarbonyl group; methylaminocarbonyl group , C2-C7 monoalkylaminocarbonyl groups such as ethylaminocarbonyl group and propylaminocarbonyl group; N, N-dimethylaminocarbonyl group, N, N-diethylaminocarbonyl group, N, N-
C3-C9 dialkylaminocarbonyl group such as methylethylaminocarbonyl group; C2-C8 alkylcarbonyloxy group such as acetyloxy group, propionyloxy group, butyryloxy group, isobutyryloxy group; benzoyloxy group An arylcarbonyloxy group having 7 to 13 carbon atoms such as toluoyloxy group and naphthoyloxy group; an aryloxy group having 6 to 12 carbon atoms such as phenoxy group and naphthyloxy group; methoxycarbonyloxy group, ethoxycarbonyloxy group , An n-propoxycarbonyloxy group, an iso-propoxycarbonyloxy group and the like, an alkoxycarbonyloxy group having 2 to 8 carbon atoms; a phenoxycarbonyloxy group, a naphthyloxycarbonyloxy group, and the like, an aryloxycarbonyloxy group having 7 to 13 carbon atoms or Like 5-membered ring group represented by the general formula (7) to (9) below.

In the present invention, particularly preferred ethylene derivatives include those represented by the following general formula [I].

[0026]

[Chemical 5]

(In the formula, ring A represents a perfluorocycloalkyl group, an acid anhydride or an optionally substituted maleimide group, and R ¹ and R ² are an alkyl group, an alkoxy group, a halogen atom or a dialkylamino group. or it represents a trifluoromethyl ^{group, R 3, R 4, R} 5, R 6, R 7, R
⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a trifluoromethyl group, a cyano group, a nitro group, a dialkylamino group or an aryl group which may be substituted. , M and n are 1 to 5
Represents However, at least one of m and n represents 2 or more. In the present invention, the ring A in the general formula [I] is substituted with a perfluorocycloalkyl group such as (16) below, an acid anhydride group such as (17) below, or a substituent such as (18) below. Examples of the maleimide group are also preferred, and here, as the substituent R of the maleimide group, a halogen atom, a lower alkoxy group,
Methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, tert-butyl group which may have a substituent such as hydroxyl group, cyano group, amino group, nitro group and phenyl group. An alkyl group having 1 to 5 carbon atoms, such as a halogen atom, a lower alkoxy group, a hydroxyl group, a cyano group, an amino group, a nitro group, a phenyl group which may have a substituent such as a phenyl group, a tolyl group, and a naphthyl group. An aryl group having 6 to 12 carbon atoms such as a group; or a halogen atom, a lower alkoxy group, a hydroxyl group, a cyano group,
A cycloalkyl group having 3 to 8 carbon atoms such as a cyclopropyl group which may have a substituent such as an amino group, a nitro group and a phenyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group is preferable.

[0028]

[Chemical 6]

Specific examples of the ethylene derivative according to the present invention include those represented by the following (A) to (L).

[0030]

[Chemical 7]

[0031]

[Chemical 8]

[0032]

[Chemical 9]

The photochromic optical recording material of the present invention having a recording layer containing such an ethylene derivative is:
It can be easily obtained according to a known method.

For example, the photochromic optical recording material of the present invention can be manufactured by forming a recording layer according to the following method (i) or (ii).

(I) A polyester resin, polystyrene resin, polyvinyl butyral resin, polyvinylidene chloride, polyvinyl chloride, polymethyl methacrylate, polyvinyl acetate, cellulose acetate, epoxy resin, or an ethylene resin, if necessary. With a binder such as a phenolic resin, dispersed or dissolved in a solvent such as carbon tetrachloride, benzene, cyclohexane, methyl ethyl ketone, tetrachloroethane, etc., and applied on a suitable substrate, or
The recording layer is formed on the substrate by, for example, vapor deposition on an appropriate substrate by a known vapor deposition method or a co-evaporation method with another compound.

(Ii) The ethylene derivative is dissolved in the above-mentioned solvent and sealed in a glass cell or the like.

In the method (i), the substrate used may be transparent or opaque to the light used. Examples of the material of the substrate material include supports for general recording materials such as glass, plastic, paper, plate-shaped or foil-shaped metal, and among these, plastic is preferable from various points. Examples of the plastic include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin, polycarbonate resin, polyimide resin, polysulfone resin and the like.

The thickness of the recording layer formed on such a substrate is 100 Å to 100 μm, particularly 1000 Å to 10 μm.
Is preferred.

Further, as a film forming method, a commonly used thin film forming method such as a vacuum vapor deposition method, a sputtering method, a doctor blade method, a casting method, a spinner method and a dipping method can be adopted.

When a binder is used for film formation,
It is desirable that the amount of the ethylene derivative according to the present invention is 5% or more by weight.

In the case of film formation by the spinner method, the rotation speed is preferably 500 to 5000 rpm, and after spin coating, treatment such as heating or applying to solvent vapor may be performed depending on the case.

When the recording layer is formed by a coating method such as a doctor blade method, a casting method, a spinner method, a dipping method, or a spinner method, the coating solvent is bromoform,
Boiling point of dibromoethane, ethyl cellosolve, xylene, chlorobenzene, cyclohexanone, etc.
Those of are preferably used.

In the present invention, a transition metal chelate compound (for example, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-) is used as a singlet oxygen quencher in the recording layer in order to improve its stability and light resistance. (alpha-diketone etc.) or a tertiary amine compound may be contained.

The recording layer of the photochromic optical recording material of the present invention may be provided on both sides of the substrate or on only one side.

Recording on the photochromic optical recording material of the present invention obtained as described above is performed by irradiating the recording layer provided on both sides or one side of the substrate or the recording layer in the cell with light focused to about 1 to 10 μm. By. Then, the light-irradiated portion undergoes a color change due to absorption of light energy. The recorded information can be reproduced by reading the difference in reflectance or absorbance between the portion where the color change due to light has occurred and the portion where the color change due to light has not occurred.

[0046]

In the ethylene derivative according to the present invention, a relatively long π-conjugated chain formed by a polyhetero five-membered ring chain is spread over the entire molecule, so that the absorption wavelength shifts to the long wavelength side and the semiconductor laser becomes It becomes sensitive.

[0047]

EXAMPLES Next, the present invention will be described more specifically with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples unless it exceeds the gist.

Example 1 [Synthesis of ethylene derivative] Compound (1-7) was synthesized by the following synthetic route. In the following, "Me"
Represents a "-CH _3".

[0049]

[Chemical 10]

Synthesis of compound (1-2) Compound (1-1) (5 g, 44.6 mmol) was added to acetic acid (50).
Dissolve in 1 ml and cool to 0 ° C, then add 5 ml of bromine (98 mmo
1) was added, and the mixture was stirred overnight while returning to room temperature. Aqueous sodium thiosulfate solution was added to this solution, extracted with ether, and dried over magnesium sulfate (yield: 7.8).
g, yield: 65%).

Synthesis of compound (1-3) 2.17 g (8.05 mmol) of compound (1-2) was dissolved in 50 ml of anhydrous ether under a nitrogen atmosphere at -60 ° C.
Cooled to. To this, 5.6 ml (8.86 mmol) of n-butyllithium hexane solution was slowly added dropwise,
Stir for 1.5 hours. Tributyl boric acid 6.5m
1 (24.2 mmol) was slowly added dropwise, and the mixture was stirred at -60 ° C for 1.5 hours. The reaction was stopped by adding water, extracted with ether, and dried over magnesium sulfate (yield:
1.1 g, yield: 71%).

Synthesis of compound (1-4) To 70 mg (0.06 mmol) of tetrakistriphenylphosphine palladium (O) in a flask was added 50 ml of dimethoxyethane under a nitrogen atmosphere, and after stirring for 3 minutes, 321 mg of 2-bromothiophene was added. (2.0 mmo
l) was added. Compound (1-3) 445mg
(2.2 mmol) and aqueous sodium carbonate solution (413 m
g / 5 ml) was added and the mixture was stirred for 5 hours and then stirred overnight.
After the solvent was distilled off, water was added and the mixture was extracted with ether and dried over magnesium sulfate (yield: 124 mg, yield: 23).
%).

Synthesis of compound (1-5) 600 mg (2.2 mmol) of compound (1-4) was dissolved in anhydrous tetrahydrofuran under a nitrogen atmosphere at -60 ° C.
Cooled to. To this, 2.0 ml (3.2 mmol) of n-butyllithium hexane solution was slowly added dropwise and stirred for 1 hour, 0.08 ml of perfluorocyclopentene was added and stirred for 3 hours, and then 0.05 ml of perfluorocyclopentene (total 0) was added. .13 ml, 1.0 mmol) was added. After stirring at -60 ° C for 3 hours, water was poured and the mixture was extracted with ether and dried over magnesium sulfate (yield: 82 m).
g (crude), yield: 13%).

Synthesis of Compound (1-6) Compound (1-5) (crude) 50 mg (0.09 m
mol) carbon tetrachloride 5 ml, acetic acid 5 ml, iodic acid 7
mg (0.04 mmol) aqueous solution was added, and after heating to 50 ° C., iodine 32 mg (0.13 mmol) was added,
The mixture was heated and stirred for 3 hours. Aqueous magnesium thiosulfate solution was added, extracted with chloroform, and dried over magnesium sulfate (yield: 43 mg, yield: 59%).

Synthesis of Compound (1-7) 256 mg of 2-methoxythiophene under nitrogen atmosphere
(2.24 mmol) was dissolved in 2 ml of anhydrous ether, and 0.39 ml (2.7 mmol) of N, N, N ′, N′-tetramethylethylenediamine and 1.68 ml (2.7 mmol) of n-butyllithium hexane solution were added. ,
Stir at room temperature for 2 hours. 1 ml of anhydrous tetrahydrofuran and 2.8 ml of zinc chloride ether solution (2.7 mm)
ol) was added and the mixture was further stirred at room temperature for 3 hours to prepare a reagent. In a separate flask, under nitrogen atmosphere, tetrakis (triphenylphosphine) palladium (O) 2.3 mg (0.
002 mmol) and compound (1-6) 23 mg (0.0
(28 mmol) was dissolved in 5 ml of anhydrous tetrahydrofuran, 2.9 ml of the above-prepared reagent was added, and the mixture was heated with stirring for 1 hour. Water and hydrochloric acid were added, the mixture was extracted with ether and dried over magnesium sulfate (yield: 10 mg, yield: 45%).

The NMR spectrum data and Mass spectrum data of the obtained compound (1-7) are as follows.

[0057]

[Chemical 11]

[Preparation of Recording Material] Compound (1-7) 10
mg and polymethylmethacrylate 1 g, toluene 2 m
It was dissolved in 1 and a thin film was formed on a glass substrate by spin coating. 366 nm wavelength from mercury lamp to the thin film
When irradiated with the light of, the color of the thin film is green (λmax: 662n
The color changed to m). This green color faded due to a semiconductor laser beam having a wavelength of 680 nm, became colorless again, and recording / erasing was confirmed.

FIG. 1 shows the state of this recording / erasing 366n.
the absorption spectrum of the ring-closed body after irradiation with m of a mercury lamp,
The absorption spectrum of the ring-opened product after fading with a semiconductor laser beam of 680 nm is shown.

Comparative Example 1 [Synthesis of Ethene Compound] Compound (1-11) was synthesized by the following synthetic route.

[0061]

[Chemical 12]

Synthesis of compound (1-8) 2.85 g (10.1 mmol) of compound (1-2) was dissolved in 25 ml of anhydrous ether and cooled to -60 ° C.
Add 10 ml of n-butyllithium hexane solution (1
(5.8 mol) was slowly added dropwise, and the mixture was stirred for 2 hours. Water was added to this to stop the reaction, which was extracted with ether and dried over magnesium sulfate (yield: 1.76 g, yield: 88).
%).

Synthesis of Compound (1-9) 1.09 g (5.74 mmol) of Compound (1-8) was dissolved in anhydrous tetrahydrofuran under a nitrogen atmosphere to produce -60.
Cooled to ° C. 4.3 ml (6.88 mmol) of n-butyllithium hexane solution was slowly added dropwise to this,
Stir for 1.5 hours, then perfluorocyclopentene 0.2
After adding 3 ml and stirring for 3 hours, 0.15 ml of perfluorocyclopentene was added again (total 0.35 ml, 2.58 mmo
l) was added. After stirring at -60 ° C for 3 hours, water and hydrochloric acid were added, the mixture was extracted with ether, and dried over magnesium sulfate (yield: 580 mg, yield: 51%).

Synthesis of Compound (1-10) Compound (1-9) (280 mg, 0.71 mmol) was added to carbon tetrachloride (10 ml), acetic acid (10 ml), and iodic acid (63 mg).
An aqueous solution of (0.36 mmol) was added, and after heating to 50 ° C., 179 mg (0.71 mmol) of iodine was added, and 3
The mixture was heated and stirred for an hour. Aqueous magnesium thiosulfate solution was added, extracted with chloroform, and dried over magnesium sulfate (yield: 380 mg, yield: 82%).

Synthesis of Compound (1-11 ) 1.13 g (5.85 mmol) of a methanol solution of sodium methylate (28%) was placed in a flask under a nitrogen atmosphere.
Then, 31 mg (0.39 mmol) of cupric oxide and 2 mg of potassium iodide were added, and the compound (1-10) 250
A methanol solution of mg (0.39 mmol) was added dropwise, and the mixture was heated with stirring for 48 hours. After the reaction was completed, water was added to the mixture, extracted with chloroform, and dried with magnesium sulfate (yield:
30 mg, yield: 17%).

The NMR spectrum data and Mass spectrum data of the obtained compound (1-11) are as follows.

[0067]

[Chemical 13]

[Preparation of Recording Material] Example 1 except that the compound (1-11) was used in place of the compound (1-7).
In the same manner as above, a thin film was prepared by dispersing it in polymethylmethacrylate. The change in the absorption spectrum when the thin film is irradiated with light having a wavelength of 280 nm is shown as a closed ring after irradiation with the light having a wavelength of 280 nm and as an open ring before irradiation. As is clear from FIG. 2, the absorption position of the ring-closed body was at a wavelength of 600 nm or less, and showed no semiconductor laser sensitivity.

[0069]

As described above in detail, the photochromic optical recording material of the present invention provides a good optical recording medium having thermal stability and sensitivity in the long wavelength region.

According to claims 2 and 3, there is provided a photochromic optical recording material having further excellent characteristics.

[Brief description of drawings]

FIG. 1 is an absorption spectrum diagram of compound (1-7) obtained in Example 1.

FIG. 2 is an absorption spectrum diagram of compound (1-11) obtained in Comparative Example 1.

─────────────────────────────────────────────────── ─── Continuation of front page (56) Reference JP-A-63-24245 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) G03C 1/73 503

Claims (3)

(57) [Claims] 1. A photochromic optical recording material comprising an ethylene derivative in which a substituent having a π-conjugated chain is introduced into the 1-position carbon and the 2-position carbon of an ethylene bond, wherein the π-conjugated chain is A photochromic light beam comprising a hetero 5-membered ring chain, wherein at least one substituent of the substituent at the 1-position carbon and the substituent at the 2-position carbon has two or more hetero 5-membered rings. Recording material. 2. The photochromic optical recording material according to claim 1, wherein the hetero five-membered ring is pyrrole, thiophene, furan, selenophene or benzo (c) thiophene, which may be substituted. Recording material. 3. The photochromic optical recording material according to claim 1 or 2, wherein the ethylene derivative is represented by the following general formula [I]:
A photochromic optical recording material, characterized in that [Chemical 1] (In the formula, ring A represents a perfluorocycloalkyl group, an acid anhydride or an optionally substituted maleimide group, and R
¹ and R ² represent an alkyl group, an alkoxy group, a halogen atom, a dialkylamino group or a trifluoromethyl group, and R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R
¹⁰ are each independently a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a trifluoromethyl group, a cyano group,
It represents a nitro group, a dialkylamino group or an optionally substituted aryl group, and m and n represent 1 to 5. However, at least one of m and n represents 2 or more. )