JPS62177543A - Optical recording method - Google Patents

Abstract

PURPOSE:To enable light writing using semiconductor laser beams by irradiating infrared rays on the optical recording medium having a monomolecular film of a diacetylene derivative or its built-up molecular films and a recording layer containing a specified compound, and then, irradiating ultraviolet rays to develop a latent image. CONSTITUTION:The optical recording medium has the monomolecular film or its built-up molecular films of the diacetylene derivative having at least both of hydrophilic parts and hydrophobic parts, and the recording layer containing at least one of the compounds represented by formula (1) and (2) in which each of R<1>-R<3> is, independently, optionally substituted aryl; each of R<4> and R<5> is an optionally substituted arylene forming conjugated double bonds with its 2 adjacent -CH=CH- groups; R<6> is H or optionally substituted aryl; and A is an anion residue, thus permitting light writing to be executed by using a compact semiconductor laser device light in weight and high-speed recording to be achieved.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention relates to an optical recording method on an optical recording medium containing a diacetylene derivative compound, and in particular to an optical recording method using an 800-900 nm infrared laser as an optical writing means. Regarding recording methods.

[Conventional technology]

Recently, optical discs have been attracting attention as a central player in office automation. Optical discs can store large amounts of documents, literature, etc. on a single disc, so
Organize and manage documents, etc. in the office efficiently. Various types of recording media are being considered for this optical disc, and those using organic materials are attracting attention because of their cost and ease of manufacture.

Diacetylene derivative compounds are known as organic materials for such recording media. Focusing on the thermochromic properties of these compounds, a recording technology for use as laser recording media was disclosed in Japanese Patent Application Laid-Open No. 147807/1983. There is. However, this specification does not include any description of what kind of laser was used or should be used, and merely states that recording was performed using a laser.

The present inventors investigated laser recording of this diacetylene derivative compound using various lasers, and found that although thermochromic recording is possible using a large, high-output laser such as an argon laser, a small and relatively It has been confirmed that laser recording cannot be performed when a low-output semiconductor laser (wavelength: 800 to 900 nm) is used. However, for practical recording media such as optical discs, it is required that optical writing be possible using a small, low-output semiconductor laser.

Furthermore, since the conventional recording layer made of a diacetylene derivative compound as described above is formed using microcrystalline powder of the diacetylene derivative compound, the distribution of diacetylene derivative compound molecules within the recording layer is It is random, and therefore has disadvantages such as the transmittance and reflectivity of light differing depending on the location, and the degree of chemical reaction.1 It cannot be said that it is necessarily suitable for high-quality, high-density recording.

On the other hand, JP-A Nos. 59-40848, 40849, and 40850 disclose organic coatings containing polymethylene compounds with a specific structure with good thermal stability. It is disclosed that since radiation in the radiation wavelength range is absorbed and heat is generated, so-called heat mode recording in which pits are formed using laser energy can be performed. However, when recording is performed by forming physical bits on the surface of a recording medium, it is necessary to ensure that the initial surface of the recording medium is sufficiently smooth and at the same time that the surface of the recording medium is not scratched even after recording. In addition to requiring sufficient care, it has been relatively difficult to perform high-density, high-sensitivity, and high-speed recording.

[Problem that the invention seeks to solve]

The present invention has been made to solve the problems of the prior art, and an object of the present invention is to enable optical writing using a small and light semiconductor laser, and to first write recorded information onto a recording medium. An object of the present invention is to provide an optical recording method in which information is recorded as a latent image, and then the recorded information is visualized and read as needed.

Another object of the present invention is to provide an optical recording method capable of high-density, high-sensitivity, and high-speed recording.

Still another object of the present invention is to provide an optical recording method that has excellent stability and can obtain high-quality optically recorded images.

[Means for solving problems]

That is, the optical recording method of the present invention comprises a monomolecular film or a cumulative film of a diacetylene derivative compound having at least a hydrophilic site and a hydrophobic site, and a compound represented by the following general formula (1) or (2). 800 to 900 JII to an optical recording medium having a recording layer containing one or more types of
A step of irradiating I+ infrared rays according to recorded information to form a latent image; and a step of irradiating an optical recording medium on which the latent image is formed with ultraviolet rays to visualize the HPr image. It is characterized by

General formula (1) % formula % () General formula (2) , center R1-C''-CH=CH-R4-C:H=CH-R3(
2)■ (In the formula, R1, R2, and R3 each independently represent an aryl group that may have a substituent, and R4 and R5 are conjugated with two adjacent -C)I=CH- groups. It represents an arylene group which may have a substituent forming a double bond system, R6 represents hydrogen or an aryl group which may have a substituent, and A represents an anion residue. ) The diacetylene derivative compound having both a hydrophilic site and a hydrophobic site (hereinafter abbreviated as OA compound) used in the present invention is defined as CEC-(j It is a compound capable of addition polymerization reaction, and typically has the following general formula 8%) (wherein, X is a hydrophilic group forming a hydrophilic site,
m and n represent integers. ) Compounds represented by:

Examples of the hydrophilic group X in the DA compound described above include a carboxyl group, an amine group, and a hydroxy group.

Examples include nitrile group, thioalcohol group, imino group, sulfonic acid group, sulfinilph, (or metal or amine salt thereof. H(CH2)I forming a hydrophobic site)
The number of carbon atoms for the alkyl group represented by ll- is
1 to 30 long chain alkyl groups are preferred. Further, n+m is preferably an integer of 1 to 30.

On the other hand, the compound represented by the general formula (1) or (2) (hereinafter referred to as a polymethylene compound) used in the present invention has an absorption peak in a wavelength range of 800 nm or more,
It is a compound that generates heat when exposed to infrared light of this wavelength.

To explain this polymethylene compound more specifically, in general formulas (1) and (2), R1, R2 and R3
are each independently a phenyl group which may have a substituent,
Represents an aryl group such as a naphthyl group.

Here, the substituents include 7 substituted amine groups such as dimethylamine, diethylamino, dipropylamino, dibutylamino, diphenylamino, phenylbenzylamino, and phenylethylamino, 7 cyclic amine groups such as morpholino, piperidinyl, and pyrrolidino, methoxy, and ethoxy. and alkoxy groups such as butoxy. R4 and R5 are two adjacent -C groups such as p-phenylene, 1,4-naphthylene, etc.
Represents an arylene group which may have a substituent that forms a conjugated double bond system with the H=CH- group. Examples of the substituent include halogen atoms such as chlorine, bromine, and iodine, alkyl groups such as methyl and ethyl, and alkoxy groups such as methoxy and nidoxy. R6 represents hydrogen or an aryl group such as a phenyl group or a naphthyl group which may have a substituent. Examples of the substituents in R1 to R3 include those similar to those exemplified.A is atE+
e [Yes] e An ionic residue, such as BFa, ClO4, CF3C
00, PF6, ('4 (→ (d)
(d)
(d) Halogen atoms such as C1, B+', ClSO3, CH3SO3, ρ e e
(→ θc2H5so3-1C3H7S
03, C4H9503, C,, H,, so3', C6
Alkyl sulfonic acid compounds such as H13SO3, θ ICH2S03, sulfonic acid compounds, '-o3sCH,,so? , LT′0
3SCH20H2S.

〈:) Kai (CH2) 6 hoe, %: +5CH2, CH20-CH2
CH2SO'P.

Alkyldisulfonic acid compounds such as You can learn about Zensysulfone positive compounds.

Specific compound examples are listed below.

Three Basada 8
Takashi Sko
5 flash work C) CJ 1d tsu Φ3
5 Sa
9 pieces
9 11W
ε8g3
SaS δ 8 6g3
2 YuC 9 0 6
9 2λ The optical recording medium used in the present invention comprises a monomolecular film or a monomolecular cumulative film of the OA compound and the polymethylene compound, and may have a one-layer mixed system, a two-layer system, or a multilayer multilayer system. good.

Here, D
A multi-layer laminated system is one in which a layer containing A compound and a layer containing a polymethylene compound are laminated.
It refers to a structure that does not include the two-layer separation system, in which one or more layers containing a compound and one or more layers containing a polymethylene compound are laminated on a substrate in a predetermined total number and order.

A typical configuration of an optical recording medium used in the present invention is shown in FIGS. 1 and 2.

In FIG. 1, a single-layer mixed recording layer 2 is provided on a substrate 1, and in FIG.
The structure in which a mixed monomolecular film of A compound 8 and polymethylene compound 7 was formed, FIG. 1(B) shows DA compound 8.
It has a structure in which a mixed monomolecular cumulative film of and polymethylene compound 7 is formed.

On the other hand, in FIG. 2, a two-layer separated recording layer 2 is provided on the substrate 1, and in FIG. A structure in which layer 2a consisting of a monomolecular film of compound 8 is laminated, the second
Figure (B) shows OA on layer 2b containing a polymethylene compound.
It has a structure in which a layer 2a made of a monomolecular cumulative film of Compound 8 is formed.

The layer 2b containing a polymethylene compound may be formed as a monomolecular film or a cumulative film thereof by a method described later.

As the substrate 1 of the optical recording medium used in the present invention, glass,
Various supporting materials such as plastic plates such as acrylic resin, plastic films such as polyester, paper, and metal can be used, but when recording by irradiating radiation from the substrate side, recording radiation of a specific wavelength is used. Use something that allows the lines to pass through.

OA previously formed on substrate l or on substrate 1
In order to form the above-mentioned superposition, 1,112 or monomolecular accumulation on the layer containing the compound or polymethylene compound, for example, 1. The Langmuir-Blodgett method (hereinafter abbreviated as LB method) developed by Lang+Wuir et al. is used. The LB method uses parent wood groups and hydrophobic groups in the molecule.
(In a molecule with a structure of This method creates a monomolecular film or an accumulated film of monomolecular layers.The monomolecular layer on the water surface has the characteristics of a two-dimensional system.When the molecules are sparsely dispersed, the area per molecule is Two-dimensional ideal gas equation between A and surface pressure n, nA=k
T holds true, resulting in a "gas film".Here, k is Portzmann's constant and T is the absolute temperature.If A is made sufficiently small, the intermolecular interaction becomes strong, resulting in "condensation q" of a two-dimensional solid (or solid membrane) to become ゛. The condensed film can be transferred layer by layer to the surface of a substrate such as glass.

In addition, a so-called mixed monomolecular film or mixed monomolecular cumulative film made of double-layered compounds can also be obtained by the same method as described above. At this time, it is sufficient that at least one of the double-layered compounds constituting the mixed monomolecular film or the mixed monomolecular cumulative film has both a hydrophilic site and a hydrophobic site,
Not all compounds are required to have both a hydrophilic site and a hydrophobic group; in other words, if at least one compound maintains a balance of amphipathic properties, a single molecule will be present on the water surface. A layer is formed, and the other compound is sandwiched between the amphiphilic compounds, eventually forming a monolayer with molecular order as a whole.

A typical method for forming the recording layer 2 will be described below.

The one-layer mixed recording layer 2 shown in FIG.
It can be obtained by forming a mixed monomolecular film of compound A and a polymethylene compound or a cumulative film thereof.

That is, first, an OA compound and a polymethylene compound are dissolved in a solvent such as chloroform, and this is developed in an aqueous phase to form a developed layer in which these compounds are developed in the form of a film. Next, to prevent this spread layer from spreading freely on the water phase and spreading too much, dividers (or floats) are used to limit the area of the spread layer and control the aggregation state of these compounds. Obtain a surface pressure ■ proportional to the state. By moving this partition plate, it is possible to reduce the developed area and control the state of aggregation of the film material, gradually increasing the surface pressure (1) and setting the surface pressure (2) suitable for producing a cumulative film. By gently vertically moving the clean substrate up and down while maintaining this surface pressure, a mixed monomolecular film of an OA compound and a polymethylene compound is transferred onto the substrate. A mixed monomolecular layer is produced in this manner, and a mixed monomolecular layer cumulative IQ having a desired degree of accumulation is formed by repeating the above operations.

To transfer the monomolecular film onto the substrate, in addition to the above-mentioned vertical dipping method, methods such as the horizontal blade method and the one-turn cylinder method can be employed. The horizontal deposition method is a method in which the substrate is brought into horizontal contact with the water surface and transferred, and the rotating cylinder method is a method in which a cylindrical substrate is rotated on the water surface to transfer a monomolecular layer onto the surface of the substrate. In the vertical immersion method described above, when a substrate with a hydrophilic surface is pulled out of water in a direction across the water surface, a monomolecular layer of the first layer of the DA compound with the parent group facing the substrate is formed on the substrate. It is formed.

As the substrate is moved up and down, one layer of mixed monomolecular film is deposited with each step. Since the direction of the film-forming molecules is reversed between the pulling process and the dipping process, according to this method, a Y-shaped film is formed in which hydrophilic groups and hydrophilic groups and hydrophobic groups face each other between each layer.

On the other hand, the horizontal deposition method is a method in which the substrate is brought into horizontal contact with the water surface and transferred, and a monomolecular layer with the hydrophobic group of the OA compound facing the substrate is formed on the substrate. In this method, there is no change in the orientation of the OA compound molecules even if they are accumulated, and an X-type film is formed in which the hydrophobic groups face the substrate in all layers.On the contrary, in all layers the parent groups are The cumulative film facing the substrate side is called a Z-type film.

The rotating cylinder method is a method in which a cylindrical substrate is rotated on the water surface to transfer a monomolecular layer onto the surface of the substrate.

The method of transferring the monolayer onto the substrate is not limited to these, but when using a large area substrate.

(A method such as extruding the substrate from a plate roll into an aqueous phase can also be used.Also, the orientation of the parent wood groups and hydrophobic groups to the substrate described above is a general rule, and can be changed by surface treatment of the substrate, etc.) .

The details of the operation for transferring these single molecules 10 are already known and are described in, for example, [New Experimental Chemistry Course 18 Interface and Colo 411, pp. 498-50, published by Maruzen.

In this way, the mixed monomolecular film and its cumulative film formed on the substrate have a high density and a high degree of order, so variations in light absorption depending on location are extremely small. Therefore, by configuring the recording layer with such a film, it is possible to achieve high-density, high-resolution recording functions such as optical recording and thermal recording, depending on the functions of the A compound and the polymethylene compound. A medium is obtained.

In addition, when forming the recording layer 2 of a two-layer separation type or a multilayer laminated type, 11! It is sufficient to laminate 1-, 1-, and 1 and more layers of the layer 2b containing a polymethylene compound on the substrate 1 in a predetermined number and order.

Layer 2a consisting of a monomolecular film of an OA compound or a cumulative film thereof
can be formed on the substrate 1 or on other layers already formed on the substrate 1 by preparing a developing solution containing a DA compound (without a polymethylene compound) and using the LB method described above.

The layer 2b containing a polymethylene compound is formed by applying a coating solution prepared by dissolving or dispersing a polymethylene compound in a suitable volatile solution onto the substrate 1 or other layers already formed on the substrate 1, and drying it in a predetermined manner. It can be formed by coating the film to a desired thickness and then drying it. Alternatively, the LB method described above can be carried out by using an organic polymer with an appropriately balanced amphipathic property, such as a polymeric fatty acid such as stearic acid or alaxic acid, as a carrier molecule in a polymethylene compound. , it can also be formed as a monomolecular film or a cumulative film thereof. Furthermore, if a long-chain alkyl group or the like is introduced into a polymethylene compound, a monomolecular film or a monomolecular cumulative film thereof can be formed with good ease of formation.

When the layer 2b containing a polymethylene compound is formed by a coating method, the solvent for forming the coating solution includes alcohols such as methanol, ethanol, and impropatul; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; N, N; - Amides such as dimethylformamide and N,N-dimethylacetamide; Sulfoxides such as dimethyl sulfoxide; Ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether; Esters such as methyl acetate, ethyl acetate, and butyl acetate; Chloroform, Examples include aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethylene, carbon tetrachloride, and trichlorethylene; and aromatics such as benzene, toluene, xylene, ligroin, and monochlorobenzene.

Incidentally, a binder made of a natural or synthetic polymer may be appropriately added to the coating liquid in order to improve the adhesion to the substrate 1 or to other layers.

Coating of such a coating liquid onto the substrate l can be carried out by a spinner rotation coating method, a dip coating method, a spray coating method,
Techniques such as a bead coating method, a Y-p-y<-coach ink method, a blade coating method, a roller coating method, and a curtain coating method are used.

If the recording layer 2 is of a single-layer mixed type, its film thickness is as follows.

Approximately 200-200 mm is suitable, especially 400-500 mm.
A range to 0 is preferred. In addition, in the case of a two-layer separation system, the suitable thickness of each layer is about 100 to 100 mm, especially 200 mm to 100 mm.
A range of 0 to 5000 A is preferred. Furthermore, in the case of a multilayer laminated system, the sum of the film thicknesses of the layers containing the individual OA compounds and the sum of the film thicknesses of the layers containing the individual polymethylene compounds are preferably about 100 A to 1 μs, particularly about 200 A to 1 μs.
The range from 5000 to 5000 is preferred.

The mixing ratio of the IIA compound and the polymethylene compound in the recording layer 2 is preferably about 1/15 to 15/l, and optimally about 1/10 to 10/l.

Note that various protective layers may be provided on the recording layer 2 configured as described above, if necessary. Further, the method of the present invention can be carried out regardless of the order in which the layers are stacked in the case of a two-layer separated system or a multi-layered system.

Furthermore, when forming the recording layer 2, its stability,
Various additives may be added to this to improve quality.

The optical recording method of the present invention can be carried out using an optical recording medium configured in this manner.

In this optical recording medium, by adding ultraviolet rays to the OA compound, the absorption wavelength of the recording layer changes and the apparent color changes. That is, the DA compound is initially almost colorless and transparent, but upon irradiation with ultraviolet rays, it polymerizes and changes into a polydiacetylene derivative compound. This polymerization occurs only by irradiation with ultraviolet light and not by the application of other physical energy such as heat. As a result of this polymerization, 620~
It has a maximum absorption wavelength of 660 nm and changes from blue to dark color. This change in hue due to polymerization is an irreversible change, and once the recording layer changes from blue to dark, it does not return to a colorless transparent film.

In addition, when this polydiacetylene derivative compound that has changed to blue or dark color is heated to about 50°C or higher, it becomes about 54°C.
It has a maximum absorption wavelength at On11 and changes to a red film. This change is also an irreversible change.

On the other hand, the inventors of the present invention have conducted various studies on the recording layer having the above-mentioned structure, and found that it is possible to heat the recording layer at an appropriate temperature that does not destroy it or change its shape, and then heat it to a molten state. It has been found that even if the recording layer is irradiated with ultraviolet rays as described above, the recording layer does not change in color from blue to dark.

In other words, this means that the change to a blue or dark film as a result of the polymerization of the DA compound due to this ultraviolet irradiation is mainly caused by O.
This is obtained by the highly ordered molecular orientation of the A compound, and when the orientation order of the OA compound within the layer is disturbed by heating the recording layer to melt the layer containing the OA compound as described above. This is thought to be due to a significant decrease in the number of molecules of OA compounds in a reactive positional relationship at the molecular arrangement level.

The optical recording method of the present invention performs recording by utilizing the characteristics of such an OA compound and the function obtained by combining it with a polymethylene compound.

An example of this recording method will be described in detail below.

First, recorded information is converted into an optical signal by a semiconductor laser via a suitable control circuit. This optical signal passes through an optical system and is placed, for example, on an optical recording medium mounting means, and is placed at a predetermined position on a disc-shaped optical recording medium having a synchronously rotating single-layer mixed recording layer as shown in FIG. The image is formed as shown in A),
Optical writing of recording information is performed using a semiconductor laser.

The semiconductor laser used at this time has an output wavelength of 80
Particular preference is given to using a 0-850 nIIl GaAs junction laser.

At this time, there is no apparent change such as discoloration at the imaging point (light irradiation area) 3, but the polymethylene compound in this area absorbs the light and generates heat, and this heat generation causes the light irradiation area 3 to change. The recording layer melts and the highly ordered orientation of the constituent molecules in this region is disturbed. As a result, the highly ordered orientation of the DA compound in the light irradiation site 3 is disturbed, and the light irradiation site 3 becomes a portion that does not change color in the later development process.

Note that the irradiation conditions of the laser beam 4 during this writing may be appropriately selected depending on the configuration of the optical recording medium used, but at least the temperature of the light irradiation area 3 melts the recording layer and changes the orientation of the constituent molecules. It is necessary to maintain a temperature that is sufficient to disrupt the order and not destroy the recording layer or deform its shape.

In this way, due to the difference in the state of the molecular orientation level in the recording layer, in other words, the light irradiation caused by the formation in the portion 5b where the highly ordered orientation of the OA compound that was not irradiated with light is maintained. A latent image consisting of a portion 5a in which the highly ordered orientation of the OA compound is disturbed is formed, and recording information is written.

Note that OA compounds are not sensitive to the semiconductor laser described above, and such optical writing has not been possible with conventional optical recording media made only of OA compounds.

Here, as described above, since no recorded information is recorded in the recording layer 2 as an optically detectable image, the written recorded information cannot be read at this stage.

Therefore, if it is desired to read recorded information, it is necessary to visualize the latent image formed on the recording layer 2.

This latent image is visualized by uniformly irradiating the optical recording medium with ultraviolet light.

This ultraviolet irradiation maintains highly ordered orientation in the recording layer. That is, the OA compound in the portion 5b that was not irradiated with light during the previous writing polymerizes and changes into a polydiacetylene derivative compound, and this portion of the recording layer has a maximum concentration of 620 to 880 nn+ as shown in FIG. 3(C). The color changes to a blue or dark-colored film 6b having an absorption wavelength. On the other hand, in the part 5a that was irradiated with infrared rays during the previous optical writing, the highly ordered orientation of the DA compound is disturbed, so the polymerization reaction of the OA compound is difficult to occur, and in this part, the non-irradiated The color change to a blue or dark film as in the area 5b does not occur. Therefore, the latent image area 5a formed during the previous writing remains the color of the original recording layer, which is almost colorless and transparent, and is changed to a blue or dark color by this ultraviolet irradiation treatment. It remains in the darkened film 6b and is visualized as a white part 6a that can be optically distinguished from the blue or dark-colored film 6b.

Note that after the treatment by ultraviolet irradiation is completed, if the recording layer 2 is heated to about 50° C. or higher as necessary,
Since the polydiacetylene derivative compound in the blue or dark-colored film 6b changes color to red as described above, the recorded information written on the recording layer 2 as a latent image is transferred to the white part 6 in the red film.
It can be visualized as a.

For this heating treatment of the recording layer, a heating means such as a heater is used, or since the recording layer contains a polymethylene compound that absorbs radiation and generates heat, the recording layer is irradiated with radiation such as infrared rays. It can be implemented as follows.

Hereinafter, the optical recording method of the present invention using an optical recording medium having a single-layer mixed recording layer has been explained.
When using a recording medium having a two-layer separated recording layer as shown in the figure, the laser beam focal point 3 is the fourth
Layer 2b containing a polymethylene compound as shown in Figure (A)
It is said that When the laser beam 4 is irradiated in this manner, the polymethylene compound contained in the layer 2b absorbs the laser beam 4 and generates heat, and this heat generation melts the portion of the layer 2a containing the OA compound above the imaging point 3. Then, according to the process described above, a latent image 5a is formed as shown in FIG. 4(B). This latent image is formed by the above-mentioned ultraviolet ray irradiation treatment and by further heat treatment as required, to produce a blue, dark color, or red li [fb
This can be visualized as an optically distinguishable white part 6a.

In the above example, a disk-shaped disk (optical disk) was used as the optical recording medium, but of course, depending on the type of substrate that supports the recording layer containing the OA compound and the polymethylene compound, it may be possible to use an optical tape, an optical card, etc. etc. can also be used.

〔Effect of the invention〕

The effects of the optical recording method of the present invention are listed below.

(1) Since a combination of a polymethylene compound and a diacetylene derivative compound is used in the recording layer, optical writing is possible using a small and lightweight semiconductor laser;
High-speed recording is possible.

Moreover, the recorded information is recorded as a latent image on the recording medium, and then the recorded information can be visualized and read as desired.

(2) At least the diacetylene derivative compound is a single molecule n
Because the recording layer is composed of λ or its cumulative film, the constituent components of the recording layer have a high density and a high degree of order.
The recording layer is formed uniformly and with good surface properties. As a result, high-quality optical recording with excellent stability at high density and high sensitivity can be performed.

(3) Optical recording using an inexpensive recording medium having a highly homogeneous, large-area recording layer becomes possible.

〔Example〕

Hereinafter, the present invention will be explained in more detail based on examples.

Example 1 - General formula C, 2H257C=C-C=C-C3H16-0
1 part by weight of the diacetylene derivative compound represented by 008 and 15 parts by weight of the polymethylene compound represented by Compound No. 3 above were mixed in chloroform at 3X10-3 mol/j!
The solution having a concentration 't' dissolved therein was developed on an aqueous phase having a pH of 6.5 and a cadmium chloride concentration of 1X10-3 mol/l. After removing the solvent chloroform, while keeping the surface pressure constant, the glass substrate whose surface had been sufficiently cleaned was gently moved up and down in the direction across the water surface at a vertical speed of 1.0 cm/min to remove the DA compound. The mixed monomolecular film and the mixed monomolecular cumulative films of 5 layers, 21 layers, 41 layers, 101 layers, and 201 layers were formed on the substrate by transferring a mixed monomolecular film of and a polymethylene compound onto a substrate. Created a recording medium.

Using the optical recording medium thus obtained, the optical recording method of the present invention was carried out as follows.

First, each of the above optical recording media is irradiated with a semiconductor laser (laser beam diameter: 1 scale, irradiation time: 200 ns/1 dot, output 5 mW) with a wavelength of 830 layers according to the recorded information to form a latent image. Formed. that time,
No apparent change was observed in the light irradiated area of each optical recording medium.

Next, after writing with this semiconductor laser was completed, each optical recording medium was uniformly and sufficiently irradiated with ultraviolet rays having a wavelength of 254 layers. Then, the area other than the area irradiated with the semiconductor laser during writing at the end of the recording layer of each optical recording medium changes color to blue, and the latent image formed earlier, that is, the negative where the area irradiated with the semiconductor laser is white, becomes blue. The image was made visible.

The evaluation of the recorded results is shown in Table 1A. The evaluation was based on a comprehensive evaluation of the sensitivity, image resolution, and contrast between the white area and the surrounding area. Particularly good results were evaluated as ■, and cases in which O1 recording was not possible or poor were evaluated as ×.

Example 2 Example 1 except that the amount of the diacetylene derivative compound was 1 part by weight and the mold of the polymethylene compound was 10 parts by weight.
An optical recording medium was prepared in the same manner as described above.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with 54n11 ultraviolet rays, and this was evaluated. The results are shown in Table 1A.

Example 3 An optical recording medium was prepared in the same manner as in Example 1 except that the amount of the diacetylene derivative compound was 1 part by weight and the amount of the polymethylene compound was 5 FIIffi parts.

for each of the optical recording media thus obtained.

After performing optical recording in the same manner as in Example 1, each optical recording medium was uniformly and sufficiently irradiated with 254 nm ultraviolet rays to visualize a negative image, and this was evaluated. The results are shown in Table 1A.

Example 4 An optical recording medium was prepared in the same manner as in Example 1 except that the amount of the diacetylene derivative compound was 1 part by weight and the amount of the polymethylene compound was 1 part by weight.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with 54 nm ultraviolet rays, and this was evaluated. The results are shown in Table 1A.

Example 5 An optical recording medium was prepared in the same manner as in Example 1 except that the amount of the diacetylene derivative compound was 5 parts by weight and the amount of the polymethylene compound was 1 part by weight.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with 54 nm ultraviolet rays, and this was evaluated. The results are shown in Table 1B.

Example 6 An optical recording medium was prepared in the same manner as in Example 1 except that the amount of the diacetylene derivative compound was 10 parts by weight and the amount of the polymethylene compound was 1 part by weight.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with 54 nm ultraviolet rays, and this was evaluated. The results are shown in Table 1B.

Example 7 An optical recording medium was prepared in the same manner as in Example 1 except that the amount of the diacetylene derivative compound was 15 parts by weight and the amount of the polymethylene compound was 1 part by weight.

for each of the optical recording media thus obtained.

After performing optical recording in the same manner as in Example 1, each optical recording medium was uniformly and sufficiently irradiated with 254 nm ultraviolet rays to visualize a negative image, and this was evaluated. The results are shown in Table 1B.

;1r] [Blind R1shi;j;; Examples 8 to 14 After optical recording and visualization of negative images were carried out in the same manner as in Examples 1 to 7, each optical recording medium was heated at approximately 80°. C
A negative image was obtained in which the blue background changed to red. The results of evaluating this negative image using the same criteria as in Example 1 are shown in Tables 2A and 2B.

Example 15 General formula “+2H2s-C=C-C=C-C:8[(,6
Instead of the diacetylene derivative compound represented by -C0OH, general formula C, H, -C=C-C=C-C2H4-C
An optical recording medium was prepared in the same manner as in Example 4 except that the compound represented by 00)I was used.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with ultraviolet rays of 54 r+m, and was evaluated. The results are shown in Table 3A.

Examples IB-20 Example I except that instead of the polymethylene compound represented by Compound No. 3, the polymethylene compounds represented by Compound No. 9.17.23.27 and 33 were used individually.
An optical recording medium was prepared in the same manner as in S.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with 54n- ultraviolet rays, and was evaluated. The results are shown in Table 3A and 3.
It is shown in Table B.

Example 21 A coating solution was prepared by dissolving 10 parts by weight of a polymethylene compound represented by /12 in 20 parts by weight of methylene chloride.

Next, a glass disk substrate (thickness 1.5 mm).

(diameter 200 mID) was attached to a spinner coater, and after first dropping a small amount of the above coating liquid onto the center of the disk substrate,
The coating was applied by rotating a spinner at a predetermined rotation speed for a predetermined time, and dried at room temperature to form a layer containing a polymethylene compound on the substrate.

After forming a layer containing a polymethylene compound in this way, Cl2H2S-CmiC-CMC-CoH+6
- A solution of an OA compound represented by C0OH in chloroform at a concentration of 3X10-3 mol/l is prepared at a pH of 6.5 and a cadmium chloride concentration of 1X10-3 mol/l.
was developed on the aqueous phase. After removing the solvent chloroform, while keeping the surface pressure constant, the glass substrate on which the layer containing the polymethylene compound, whose surface had been thoroughly cleaned, was formed was moved at a vertical speed of 1.0 cm/min in the direction across the water surface. Transfer the monomolecular film of the OA compound to the surface of the layer containing the polymethylene compound by gently moving it up and down. An optical recording medium formed on the above was prepared.

The thickness of the layer containing the polymethylene compound and the cumulative number of monolayers were varied as shown in Table 4A.
Twenty-five types of optical recording media, samples N621-1 to 21-25, were obtained.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with 54 nm ultraviolet rays, and was evaluated. The results are shown in Table 4B.

Example 22 General formula C'12H2S-Cmi c-c= C-Cs Hl
In place of the diacetylene derivative compound represented by G-0008, the general formula (o H+ q-CEC-CHC-c
Sample acids 22-1 to 22-25-2 as shown in Table 5A were prepared in the same manner as in Example 21, except that a diacetylene derivative compound represented by 2H4-COOH was used.
Five types of optical recording media were obtained.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
A negative image was visualized by uniformly and sufficiently irradiating it with 54 ns ultraviolet rays, and this was evaluated. The results are shown in Table 5B.

Example 23 In the coating liquid for forming a layer containing a polymethylene compound, instead of the polymethylene compound represented by Compound 2,
Twenty-five types of optical recording media, sample acids 23-1 to 23-25 as shown in Table 6A, were obtained in the same manner as in Example 22, except that the polymethylene compound represented by Compound 5 was used. .

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with ultraviolet rays of 54 r+m, and was evaluated. The results are shown in Table 6B.

Example 24 The same method as in Example 22 except that the polymethylene compound represented by Compound 10 was used instead of the polymethylene compound represented by Compound 2 in the coating solution for forming a layer containing a polymethylene compound. Accordingly, 25 kinds of optical recording media of sample compounds 24-1 to 24-25 as shown in Table 7A were obtained.

Example 1 was applied to each of the optical recording media thus obtained.
After performing optical recording in the same manner as above, two
The negative image was visualized by uniformly and sufficiently irradiating it with 54 nm ultraviolet rays, and this was evaluated. The results are shown in Table 7B.

[Brief explanation of drawings]

FIG. 1(A), FIG. 1(B), FIG. 2(A), and FIG. 2(B) are schematic cross-sectional views illustrating one aspect of the structure of an optical recording medium used in the method of the present invention, respectively; Figure 3 (A) - 3rd
FIG. 4(C) and FIGS. 4(A) to 4(C) are schematic cross-sectional views of an optical recording medium showing the optical recording process of the present invention, respectively. 12 substrate 2: Recording layer 2a: [] Layer containing compound A 2b: Layer 3 containing polymethylene compound: Light irradiation area 4: Laser beam 5a: Latent image 5b: Non-irradiation area 6d: White area 6b: Discoloration area 7: Polymethylene compound 8: Mouth A compound

Claims (1)

[Scope of Claims] 1) A monomolecular film or a cumulative film of a diacetylene derivative compound having at least a hydrophilic site and a hydrophobic site, and one or more compounds represented by the following general formula (1) or (2). A step of irradiating an optical recording medium having a recording layer containing the above with infrared rays of 800 to 900 nm according to recorded information to form a latent image; An optical recording method comprising the step of irradiating the latent image to visualize the latent image. General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) General formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (In the formula, R^1, R^2, R^ 3 represents an aryl group that may each independently have a substituent, and R^4 and R^5 are substituents that form a conjugated double bond system with two adjacent -CH=CH- groups. (R6 represents an arylene group which may have hydrogen or a substituent, and A represents an anion residue.) 2) Ultraviolet irradiation treatment of the optical recording medium 2. The optical recording method according to claim 1, further comprising a step of heating the optical recording medium after the step.