JPS62176885A - Optical recording method - Google Patents

Abstract

PURPOSE:To make it possible to record a high density and high sensitivity pit at a high speed by irradiation with low output semiconductive laser beam, by containing a specific diene compound salt and a polydiacetylene derivative in the recording layer of an optical recording medium in combination. CONSTITUTION:An optical recording medium having a recording layer 2 containing a polydiacetylene derivative and one or more of a diene compound salt represented by general formula I or II is formed. Next, recording information is converted to an optical signal by a semiconductive laser beam through a control circuit to be formed into an image on the recording layer 2 of the optical recording medium. The diene compound salt present at the image forming point (area) 3 absorbs this laser beam 4 to generate heat and the recording layer 2 is melted to form a pit consisting of a recessed part 5.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an optical recording method using an optical recording medium, and in particular, to a high-density, high-sensitivity, high-speed pit recording even when using a low-output semiconductor laser. The present invention relates to an optical recording method that is advantageous in terms of energy saving and that enables the following.

(Prior Art) Recently, optical recording media such as optical disks, optical tapes, and optical cards (hereinafter collectively referred to as optical disks) have been attracting attention as central players in office automation.For example, optical disks are A large amount of documents, documents, etc. can be recorded and stored in the .
It has the advantage that management can be carried out efficiently.

The recording layer used in such optical disk technology can store high-density information by forming optically detectable small dots (for example, IIAJn size) in the form of spiral or circular tracks.

For example, the disc used in this optical disc technology has a recording layer made of a material sensitive to laser.
(A typical configuration is a disk with a structure installed on a plate. To write information on this disk, a laser focused on the laser sensitive layer (recording layer) is scanned, and dots are created only on the surface that is irradiated with this laser beam. Depending on the recorded information, the dots are formed in the form of spirals or circular tracks, ie the laser-sensitive layer is capable of absorbing laser energy to form optically detectable dots.

For example, in the heat mode recording method, the laser sensitive layer absorbs thermal energy and can form dots consisting of small pits due to evaporation or melting at that location. In another beat mode recording method, absorption of the applied laser energy can form a dot of optically detectable discoloration at that location.

Information recorded on this optical disk is detected by scanning a laser along a track and reading optical changes in areas where dots are formed and areas where dots are not formed. For example, when using a disk with a recording layer provided on the reflective surface of a ζ plate, a laser is scanned along a track, and the energy reflected by the disk is monitored by a photodetector. In the case of pit recording, the output of the photodetector decreases in areas where pits are not formed, while in areas where bits are formed, the laser beam is sufficiently reflected by the underlying reflective surface and the photodetector is The output of the detector becomes larger.

The recording layer of such optical discs has conventionally been made of a variety of materials, including metal thin films such as aluminum evaporated films, bismuth thin films, tellurium oxide films, and chalcogenide amorphous glass films mainly using inorganic materials. However, due to the cost and ease of manufacture, there is interest in using organic materials.

As organic materials used for optical recording media, Japanese Patent Application Laid-Open No. 59-8
No. 4248 and JP-A-59-84249 disclose an organic liquid 11 containing a diene compound having a specific structure with good thermal stability.
! It is known that a percussion film containing these compounds absorbs radiation in the semiconductor laser radiation wavelength range and generates heat, so that so-called heat sword recording in which pits are formed using laser energy can be performed. ing.

(Problem to be solved by the invention) However, although the conventional pit recording method has the advantage of clear recording, that is, good contrast, compared to a set of recording nozzles that form dots due to discoloration, However, recording requires more energy and the recording speed is slower.Historically, since physical pits are formed on the surface of the recording medium, the initial surface of the recording medium was not sufficiently smooth. At the same time, sufficient care must be taken not to damage the surface of the recording medium even after recording, and it has been difficult to perform recording with high density and high sensitivity.

For example, when the recording layer of an optical recording medium is formed from the above-mentioned diene compounds, these compounds absorb semiconductor laser beams (infrared rays) and generate heat, and as a result of the heat generation, they self-melt. Pit can be formed in an optical recording medium. However, it requires a large amount of energy to form pits, has low sensitivity, and requires a relatively long constant exposure (light irradiation) time. Therefore, it was not possible to shorten the exposure time and recording at higher speeds was not possible.

The present invention has been made in order to solve the problems of the prior art, and the present inventors have proposed a method of forming a recording layer of an optical recording medium by combining a planar diene compound and a diacetylene conductor compound. They found that the pit formation rate under light irradiation was significantly accelerated even when a low-power semiconductor laser was used, and the present invention was completed.

An object of the present invention is to provide an optical recording method that enables optical writing using a small, light-weight, and low-output semiconductor laser, and also enables high-speed recording.

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

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

[Means for solving problems]

4-That is, the optical recording method of the present invention provides an optical recording medium having a recording layer containing a polydiacetylene derivative compound and one or more compounds represented by the following general formula (1) or (2). The method is characterized by comprising a step of irradiating light in accordance with recorded information to form a pit consisting of four parts in the recording layer.

General formula (+) ♀ General formula (2) (wherein, R1 represents an alkyl group, a substituent together with phenyl or styryl group, R2 and R
h is two adjacent −(:11 = (:ll −J
, L and "arylene which may have a substitution JJj forming a bond system", L, and RA and R7 are substituted J, a phenyl group which may be substituted with L, or naphthyl J, L , R4 represents an alkoxy group, R represents an alkyl group, and A represents an anionic residue.)
The 4T diacetylene derivative compound (hereinafter abbreviated as 〇he compound) contained in the optical recording medium used in the method of the present invention has the following general formula % formula % (: (where R and R' are polar ", L: Alkyl which may be substituted with a polar group, t, saturated aliphatic hydrogen such as a cyclohexyl group" J:: An alkyl group which may be substituted with a polar group, such as a vinyl group or a propenyl group. An olefinic hydrocarbon group; or an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, or an alkylphenyl group, which may be substituted with a polar group; , (or metal or amine salts thereof,
sulfonic acid group or its metal or amine salt, sulfamide group, amide group, amino group, imino group, hydroxy group, oxyamino group, diazonium group, guanidine'',
c, hydrazine group, phosphoric acid group, silicic acid group, aluminate group, nitrile group, thioalcohol group, nitro group and halogen atom. ) and their polymers.

Furthermore, as will be described later, when the recording layer is formed from a monomolecular film or a cumulative film of Cli molecules, the crystalline compound has a 1°4-
Compounds capable of 1-1 addition reaction, typically represented by the general formula % (%) (wherein, x is the xylophilicity J, t, which forms a hydrophilic site, m, (n represents an integer.) Compounds represented by these are included.

In this case, wood-philicity (x) is, for example, a carboxyl group, an amino group, a hydroxyl group, a nitrile J1c
, thioalcohol group, imino group, sulfonic acid, (, sulfinyl), (or its metal or amine salt.The alkyl group represented by 11 (C112) which forms a hydrophobic site has a carbon atom number of A long chain alkyl group of 1 to 30 is preferable. Also, n+m is 1
An integer of ˜30 is preferred.

On the other hand, the general formula (+) or (+iif) used in the present invention is
The compound represented by 2) (hereinafter referred to as diene compound salt) has an absorption peak in the wavelength range of 750 nm or more.
1-C is a compound that generates heat when exposed to infrared light of this wavelength.

To explain this diene compound salt more concretely,
In general formulas (1) and (2), R1 is methyl, ethyl,
Represents an alkyl group such as propyl, isopropyl, butyl, hexyl, phenyl which may have a substituent, ζ or styryl, +, t, 4-0 Substituted here 1L is methoxy, ethoxy, butoxy, etc. alkoxy group, halogen atom such as chlorine, bromine, iodine, alkyl such as methyl, ethyl, propyl, isopropyl, (, nitro)1
t, can be given. R2 and Hb are two adjacent -(:1l=
Represents an arylene group which may have a substituent that forms a conjugated double bond system with the C11 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 ethoxy.

R3 and R7 represent a phenyl group or a naphthyl group which may have a substituent. Examples of substituents include substituted amino groups such as dimethylamino, diethylamino, dipropylamino, dibutylamino, diphenylamino, phenylamino, phenylbenzylamino, and phenylethylamino, cyclic amino groups such as morpholino, piperidinyl, and pyrrolidino, methoxy, ethoxy, Examples include alkoxy groups such as butoxy. R4 represents an alkoxy group such as methoxy, ethoxy or butoxy. R″ represents an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, hexyl, etc. A is an anionic residue, such as [IF?, co2.
cF3eta, PF? , hunting i, P, cosop, CI
+3Snu, C7H5S02C3H7SO2C4H9SO
? C3H3IS02C6H,3so3, (:H:
IsO: 1. C1(:II, CH25o
3, CH,>Cll-503, ICH, SO3, Book C11, Material CH:.

c + -<”'a-c++, s9, CXc112(1
: H2S03, θ0. ．． S(:H, sop, θ.35
CH2(:11.S2.

eo3scH, co-co, hoe, θ03SC)l, C
Il, CH25op, C1(3 C035C)12co, CH2(:lI, CH2(:1
1. Hoe, θ03SCH, CI+, -0-ell, C
H, 503, Sun◇.

Specific examples of this diene compound are illustrated below.

A typical configuration of the optical recording medium used in the present invention is shown in FIG. In this example, a recording layer 2 containing the aforementioned 〇 crystal compound and a diene compound salt is provided on a substrate 1.

The recording layer 2 of the optical recording medium used in the present invention contains the above compound and the diene compound salt. Create a coating liquid by mixing 7 parts with the solvent and apply this coating liquid to the substrate, or deposit a mixed monomolecular film or a mixed monomolecular film stack of the crystal compound and diene compound salt on the substrate. It can be obtained by a method such as forming.

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

Add the crystal compound and diene compound salt to the substrate!
4. Apply a coating solution prepared by mixing with a volatile solvent of 1″11.
When forming the recording layer 2 by the method of
In order to improve the adhesion between the first liquid and the substrate 1,
A binder made of a natural or synthetic polymer may be added as appropriate. Furthermore, various additives may be added to improve the stability and quality of the recording layer 2.

The solvent used for coating is appropriately selected depending on the type of binder used and the type of D-formula compound and diene compound salt, but in general, alcohols such as methanol, ethanol, isopropanol, acetone, methyl ether, etc. Ketones fi, N, N, such as ketones and cyclohexanone
- Ketones such as dimethylformamide, ■, N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide; Needles such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether; Esters such as methyl acetate, ethyl acetate, and butyl acetate: Aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, trichloroethylene, etc.; and 100% hydrocarbons such as henzene, toluene, xylene, monochlorobenzene, dichlorobenzene, etc.

l like this? Applying the cloth liquid to the plate 1 is performed using a spinner spin coating method, a dip coating method, a spray coating method, a bead coating method, a wire bar coating method, a blade coating method, a roller coating method, a curtain coating method, etc. method is used.

In this case, the number of membranes for the recording layer 2 is 500 to 2
A number of approximately μ is suitable, and a range of 1,000 to 5,000 people is particularly preferred. The blending ratio of the D formula compound and the diene compound salt in the recording layer 2 is preferably about 1715 to 1071,
Optimally, it is 1710-5/I.

On the other hand, a typical structure of an optical recording medium used in the method of the present invention in which the recording layer 2 is formed from a monomolecular film or a monomolecular cumulative film is illustrated in FIGS. 4 and 5. In the example shown in FIG. 4, a recording layer 2 made of a mixed monomolecular film of a compound 7 and the diene compound salt 6 is formed on a substrate 1, and a fifth layer is formed on the substrate 1.
The figure shows a mixed monomolecular cumulative film of these.

In order to form the recording layer 2 made of such a monomolecular film or a monomolecular cumulative film on the substrate 1, for example, I, Lan
The Langmuir-Prodgett method (hereinafter abbreviated as LB method) developed by Gmuir et al. is used.

The LB method uses a molecule with a structure that has a parent wood group and a hydrophobic group in one molecule, and when the balance between the two (balance of amphiphilicity) is maintained moderately, this molecule forms a hydrophilic J &
This is a method of creating a monomolecular film or an accumulated film of monomolecular layers by utilizing the fact that the monomolecular layer is turned downward. A monolayer on the water surface has the characteristics of a two-dimensional system. When the molecules are sparsely dispersed, the two-dimensional ideal gas equation, nA=kT, holds between the area A per molecule and the surface pressure n, resulting in a gas film. Here, k is Boltzmann's constant and T is absolute temperature. If A is made small enough, an intermolecular phase t7. The action becomes stronger and becomes a two-dimensional solid °°condensed film (or solid film)′°. Condensation films are made of glass, etc.
, can be transferred layer by layer to the surface of the L plate.

Also, a so-called mixed monomolecular film or mixed monomolecular cumulative film composed of two or more compounds can be obtained by the same method as described above. At this time, it is sufficient that at least one of the two to seven compounds constituting the mixed monomolecular film or mixed monomolecular cumulative film has both a hydrophilic site and a hydrophobic site,
Not all compounds are necessarily required to have both a hydrophilic part and a hydrophobic group in a hydrophobic part. In other words, if the amphipathic balance of at least one compound is maintained, a monomolecular layer will be formed on the water surface, and the other compounds will be sandwiched between the amphipathic compounds, resulting in a well-ordered molecular layer as a whole. A monolayer is formed.

Using this method, a mixed monomolecular film or mixed monomolecular stack of a DA compound and a diene compound salt constituting the recording layer of the present invention is produced, for example, as follows. First D
A compound of the formula and a diene compound salt are dissolved in a solvent such as chloroform, and this is added to the aqueous phase -L to form a developed layer in which these compounds are developed in the form of a film. A partition plate (
or 11) is provided to limit the area of the developed layer to control the state of aggregation of these compounds, and to obtain a surface pressure n proportional to the state of aggregation. By moving this partition plate, the developed area can be reduced to control the agglomeration state of the membrane material, and the surface pressure can be gradually increased to set a surface pressure n suitable for cumulative production. By gently moving the clean substrate vertically up and down while maintaining this surface pressure, a mixed q1-molecule film of the compound of formula ○ and the diene compound salt is transferred onto the substrate.

The mixed monolayer is thus f! A: A mixed monomolecular layer cumulative film having a desired degree of accumulation can be formed by repeating the +if operation.

In order to transfer the molecule film to the substrate, other than the above-mentioned vertical immersion 6°1 method, methods such as the horizontal adhesion method and the rotating 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, a substrate with a hydrophilic surface is pulled out of the water in a direction across the water surface. - Geroto, one layer] Is 1 a hydrophilic group of the compound of formula ○?Is lil facing the L plate side, a molecular layer?
, (It is formed into a plate. When the substrate is lowered, 8 molecules + 1rA are stacked one layer at each step. Therefore, according to this method, a Y-type film is formed between each layer in which the parent wood group and the hydrophilic group, Xl (, hydrophobic group), L and hydrophobic group J and c face each other.

On the other hand, the horizontal adhesion method is a method in which the J, t-plate is brought into contact with the water surface and transferred, and the hydrophobicity of the DA compound is transferred.
A lit molecular layer is formed on the substrate with : facing the J and L plates. In this method, there is no change in the orientation of the D-crystal compound molecules even if they are accumulated, and an X-type compound with the hydrophobic layer facing the substrate is formed in all layers. On the other hand, a cumulative film in which all the layers are hydrophilic and faces toward the substrate 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 monomolecular layer onto the substrate is not limited to these methods, and when using a large-area substrate, a method of extruding the substrate from a substrate roll into an aqueous phase may also be used.

Furthermore, the orientation of the multiple parent wood groups and hydrophobic groups toward the substrate is a general rule, and can be changed by surface treatment of the substrate, etc.

Details of these monomolecular film transfer operations are already known and are described, for example, in "New Experimental Chemistry Course 18 Interfaces and Colloids", pages 498-507, 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, depending on the functions of the D crystal compound and the diene compound salt,
A recording medium having a high-density, high-resolution recording function capable of optical recording and thermal recording can be obtained.

In this case, the thickness of the recording layer (cumulative number of single molecules) is:
A range of 5 to 400 is suitable, and a range of 20 to +70 is particularly preferred. The compounding ratio of the compound of formula ○ and the diene compound salt in the recording layer is the same as in the case of the coating method described above.

Note that various protective layers may be provided on the recording layer configured in this way depending on safety.

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 applying light to the D crystal compound (excluding the polymer), the absorption wavelength of the recording layer changes and the apparent color changes. That is, the DA compound (excluding the polymer) is initially almost colorless and transparent, but upon irradiation with ultraviolet rays, it undergoes 1n combination and changes into a polydiacetylene derivative compound. This 1-r coupling 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, it has a maximum absorption wavelength between 620 and 660 m, and changes from blue to dark in color. The change in hue due to this polymerization is an irreversible change, and once +? A recording layer that has changed color or dark color will not return to a colorless transparent film.

Furthermore, when a semiconductor laser is irradiated onto the recording layer containing the polydiacetylene derivative compound and the diene compound salt which has changed color from blue to U6, the diene compound salt absorbs the light and generates heat, and the heat causes the light in the recording layer to The irradiated area melts. The energy required for melting at this time is significantly smaller than when the recording layer is formed using diene compound salt alone.

The optical recording method of the present invention performs recording by utilizing the characteristics obtained by the combination of a compound and a diene compound salt. This recording method will be explained in detail below.

As the semiconductor laser used in the method of the present invention, it is particularly suitable to use a GaAs junction laser with an output wavelength of 800 to 850 nm.

When carrying out the optical recording method of the present invention, when using an optical recording medium having an optical recording layer containing an OA compound (excluding ff1 combination) and a diene compound salt, first, The entire recording layer is irradiated with ultraviolet light.

By irradiating this ultraviolet ray, the D in the recording layer is
The ^compounds (excluding the ff1 combination) are fused and changed into polydiacetylene derivative compounds, and the recording layer changes color to 11 colors to a dark color film.

(Of course, polydiacetylene directly as an OA compound,
This operation is not required for 4T recording layers using derivative compounds. )−h′, the recorded information is
It passes through a control circuit and is converted into an optical signal by a semiconductor laser. This optical signal passes through an optical system, is placed on, for example, an optical recording medium mounting means, and is imaged at a predetermined position on a synchronously rotating disc-shaped optical recording medium, as shown in FIG. The imaging position is the recording layer 2 of the optical recording medium.

The diene compound salt present at the imaging point (site) 3 absorbs this laser beam 4 and generates heat. The heat generated by the diene compound salt melts the recording layer 2 at the imaging point 3, and a bit consisting of a recess 5 is formed as shown in FIG. that time,
The recording layer 2 of the recording medium used in the present invention is composed of a combination of a diene compound salt and a polydiacetylene derivative compound as described above. The above-mentioned bit formation is greatly promoted.In other words, compared to pit formation in a recording layer composed of diene compound salt alone, it is highly sensitive to semiconductor lasers, and when using a semiconductor laser with the same output power. In some cases, the exposure time using the laser beam may be shorter.

In this way, optical recording is performed by forming pits in the recording layer according to manual information.

In the above example, the optical recording medium is a disc-shaped disk (
An optical disc) was used, which of course supports a recording layer containing a crystal compound and a diene compound salt.
4 Depending on the type of board, optical tape, optical cards, 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 the recording layer contains a combination of a diene compound salt and a polydiacetylene derivative compound, high-sensitivity and high-speed recording can be carried out even when a small, light, high-speed conductor laser is used.

(2) Since the recording layer is formed uniformly and with good surface properties, stable and high-quality optical recording can be carried out. Historically, when the recording layer is formed of a mixed molecular film of a compound and a diene compound salt or a cumulative 11q thereof, the recording layer has a higher density and a higher degree of order, and therefore Higher density and more homogeneous recording is possible.

(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 2C,,H,5-(j[kneeC=(kneeC,,H,
6-(:00+1 1 ylth part of a fine crystalline powder of a diacetylene derivative compound and 15 parts by weight of a diene compound salt represented by the above compound 7Ll were mixed with methylene chloride:
The solution was added to 10 parts by weight and thoroughly stirred to prepare a coating solution.

Next, a glass disk substrate (thickness 1.5 mm, diameter 200 mm) was mounted on a spinner coating machine, and a small drop of the coating solution was applied to the center of the disk substrate, and then the spinner coating was applied at a predetermined rotation speed. Rotate the time spinner and paint
Optical recording media were prepared by drying L/, at room temperature, and having coating film thicknesses of 500, 1,000, and 2,000 after drying on the board, respectively.

Each of the optical recording media obtained in this way was first given 25
The recording layer was uniformly and sufficiently irradiated with 4 nm ultraviolet rays to turn the recording layer into a blue film.

Next, this blue II! Optical recording was performed on each optical recording medium having a binary recording layer under the following recording conditions, except that the laser beam irradiation time per pit was varied from 400 ns to 5 μs.

Semiconductor laser wavelength: 830 r+m Laser beam diameter: 1 IAj+ Laser output: After recording under conditions of 3 mW or more, the recording results on the external light recording medium were observed using a microscope.

We investigated the laser beam irradiation time required to form pits consisting of clear concavities in the laser beam irradiation area.

The results are shown in Table 1.

Next, the optical recording media recorded with an irradiation time of 900 ns/1 pit were comprehensively evaluated in terms of resolution and contrast ratio between pit and non-pit areas. Items that could not be completed or were defective were marked with an X. The results are shown in Table 1.

Example 2 The amount of diacetylene derivative compound is l m! Example 1 A mixed solution containing iL part, l0fi'ii: part of diene compound salt 117, and 20 parts by weight of methylene chloride was used as the coating liquid. An optical recording medium was prepared in the same manner as described above.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating the recording layer with 4 nm ultraviolet rays to turn the recording layer into a blue film, optical recording was carried out in the same manner as in Example 1, and this was evaluated. Table 1 shows the evaluation of the recorded results.

Example 3 A mixed solution containing 1 part of diacetylene derivative compound, 5 parts by weight of diene compound salt, and 12 parts by weight of methylene chloride was used as the coating solution, and the same method as in Example 1 was carried out. An optical recording medium was created.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating the recording layer with 4 nm ultraviolet rays to turn the recording layer into a blue film, optical recording was carried out in the same manner as in Example 1, and this was evaluated. Table 1 shows the evaluation of the recorded results.

Example 4 The same method as in Example 1 was carried out using a mixed solution containing 1 part by weight of the diacetylene derivative compound, 1 part by weight of the diene compound salt, and 4 parts by weight of methylene chloride as the coating liquid. An optical recording medium was created.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating the recording layer with 4 nm ultraviolet rays to make the recording layer blue +11A, optical recording was carried out in the same manner as in Example 1, and this was evaluated. Table 1 shows the evaluation of the recorded results.

Example 5 5 parts by weight of 1 il of diacetylene derivative compound, ! of diene compound salt! An optical recording medium was prepared in the same manner as Example 1 using a mixed solution containing 1 part by weight of [[] and 127 parts of methylene chloride fat as a coating liquid.

for each of the optical recording media thus obtained.

First, the recording layer was uniformly and sufficiently irradiated with 254 nm ultraviolet rays to make the recording layer blue +1Q, and then optical recording was performed in the same manner as in Example 1, and this was evaluated. The recorded results are shown in Table 1.

Example 6 The total amount of diacetylene derivative compound was 1 part of Ior[iH, 1 part of itt of jlt of diene compound salt, 20 parts of fi+1 of methylene chloride! An optical recording medium was prepared in the same manner as in Example 1 using a mixed solution of 11 parts as a coating liquid.

Each of the optical recording media obtained in this way was first given 25
The recording layer was irradiated uniformly with 4 nm ultraviolet light for 1 minute.
After forming a renal color membrane, optical recording was performed in the same manner as in Example 1, and the results were evaluated. Table 1 shows the evaluation of the recorded results.

Example 7 151 parts of the diacetylene derivative compound and 1 part of the diene compound salt! 11 parts, I+1 of methylene chloride a o +9. An optical recording medium was prepared in the same manner as in Example 1, using the lu solution as the itt part as a coating liquid.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating 4 nm ultraviolet rays to make the recording layer a blue film, optical recording was performed in the same manner as in Example 1.
Shi, I rated this. Table 1 shows the evaluation of the recorded results.

Comparative Example 1 An optical recording medium was prepared in the same manner as in Example 1, without using a diene compound salt, but using a solution prepared by adding one part of a diacetylene derivative compound to two parts of methylene chloride as a coating liquid. Created.

Each of the optical recording media obtained in this way was first given 25
After uniformly irradiating 4 nm ultraviolet light for 1 minute to turn the recording layer into a blue film, optical recording was carried out in the same manner as in Example 1, and this was evaluated. Table 1 shows the evaluation of the recorded results.

Comparative Example 2 Optical recording was carried out in the same manner as in Example 1, without using a diacetylene derivative compound, but using a solution prepared by dissolving one part of diene compound salt 11i, '+ in one part of methylene chloride double h as a coating liquid. Created media.

Each of the optical recording media thus obtained was directly irradiated with a semiconductor laser beam under the same conditions as in Example 1 according to manual information, without performing ultraviolet irradiation, to perform recording. Table 1 shows the evaluation of the recording results.

Example 8 I llj ll +1+ of diacetylene derivative compound
A mixed solution containing 1 part of diene compound salt, 1 part of diene compound salt, 4 parts of methylene chloride, and 1 part of nitrocellulose as a binder was applied. Example 1
An optical recording medium with a recording layer thickness of 3,000 layers was prepared in the same manner as described above.

This optical recording medium was uniformly and sufficiently irradiated with 254 nm ultraviolet rays to make the recording layer h-color 11Q, and then recording was performed under the following recording conditions according to manual information. In addition,
Laser beam irradiation time per pit is 400ns
Various changes were made between ~5 μs.

Semiconductor laser wavelength: 840nm Laser beam diameter: ! Scale laser output crab 3 mW Comparative example 3 A solution prepared by dissolving 2 parts by weight of a diene compound salt and 2 parts by weight of nitrocellulose in 4 parts of methylene chloride was used as a coating solution without using a diacetylene derivative compound. An optical recording medium with a recording layer thickness of 3,000 layers was prepared by the same method as in Example 1.

This optical recording medium was directly irradiated with a semiconductor laser beam under the same conditions as in Example 8 using human power ++'im, without performing ultraviolet irradiation, to perform recording.

Regarding the optical recording medium of Example 8, as a result of microscopic observation, good recording was performed when the irradiation time was 1000 ns/1 pit or more, but for the optical recording medium of Comparative Example 3, 18 to clearly form two pits
An irradiation time of 0.00 s and 71 pits or more was required.

Example 9 General formula Cl2H2h-Cmic-c=c-coH,6-c
o Instead of the diacetylene derivative compound represented by
An optical recording medium was prepared in the same manner as in Example 3 except that the compound represented by 011 was used.

The optical recording medium thus obtained was first uniformly and sufficiently irradiated with 254 nm ultraviolet rays to form an eight-color recording layer, and then recording was carried out under the same recording conditions as in Example 1, with clear pits. The light irradiation time required for the formation of , the resolution, and the contrast ratio between pits and non-pits were evaluated. The results are shown in Table 2.

Examples 10 to 14 Example 9 except that the diene compound salts represented by the aforementioned compounds Makoto 3, 8.12.15 and 2o were used in place of the diene compound salt represented by Compound A I, respectively. An optical recording medium was prepared in the same manner as described above. Each of these optical recording media was first uniformly irradiated with 254 nm ultraviolet light for 1 minute to turn the recording layer into a blue film, and then Example 1
Optical recording was carried out in the same manner as above and evaluated. The 2f values of the recorded results are shown in Table 2.

Table 2 Actual hfi example 15 = General formula C,, H, 5-Ci C-CE (nee C,,
A solution in which 1jl'i parts of a diacetylene derivative compound represented by H,b-coon and 171 parts of a diene compound salt +5ili represented by compound A1 of 11η are dissolved in chloroform at a concentration of 1XlO = mol/l. of,
It was developed in an aqueous phase having a pH of 6.5 and a cadmium chloride concentration of 1X10-j mol/l. After removing the solvent chloroform, while keeping the surface pressure constant, the glass substrate whose surface had been thoroughly cleaned was gently lowered in a direction across the water surface at a vertical speed of 1.0 cm/min. Optical recording in which a mixed ili molecular film of a 0^ compound and a diene compound salt is transferred onto a substrate, and a mixed polymer 1' film and a mixed monomolecular cumulative film accumulated in the 21st, 41st, or former layers are formed on the substrate. Created media.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating 4 parts m of ultraviolet light to make the recording layer a six-color film, optical recording was carried out in the same manner as in Example 1, and this was evaluated. Table 3 shows the evaluation of the recorded results.

Example 16 An optical recording medium was prepared in the same manner as in Example 15, except that the diacetylene derivative compound was used as a single Jit part for the diene compound salt r o Hl jy part.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating 4 parts m of ultraviolet light to turn the recording layer into a blue film, optical recording was carried out in the same manner as in Example 1, and this was evaluated. Table 3 shows the evaluation of the recorded results.

Example 17 An optical recording medium was prepared in the same manner as in Example 15, except that 1 part by weight of the diacetylene derivative compound was used for 5 parts by weight of the diene compound salt.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating 4 parts m of ultraviolet light to turn the recording layer into a blue film, optical recording was carried out in the same manner as in Example 1, and this was evaluated. Table 3 shows the evaluation of the recorded results.

Example 18 An optical recording medium was prepared in the same manner as in Example 15, except that the diacetylene derivative compound was used in an amount of 411 parts I+lt per 1 ffl part of the diene compound salt.

for each of the optical recording media thus obtained.

First, the recording layer was uniformly and sufficiently irradiated with 254 parts of ultraviolet rays to form a blue film, and then optical recording was carried out in the same manner as in Example 1, and the resultant f value was determined. Table 3 shows the 1.1 value of the recorded results.

Comparative Example 4 An optical recording medium was produced in the same manner as in Example 15, except that only a diacetylene derivative compound was used without using a diene compound salt.

Each of the optical recording media obtained in this way was first given 25
The recording layer was irradiated uniformly with 4 m of ultraviolet light for 11 minutes, and the recording layer was
After forming a one-color film, optical recording was performed in the same manner as in Example 1, and the results were evaluated. The 1if values of the recorded results are shown in Table 3.

Table 3 Example 19 General 2C,,H,, -C=(knee(jC-C1IH,,
(In place of the diacetylene derivative compound represented by :0 leaves, the general formula Co) It 7- (:=C-CmiC-C
, H, -COO11 was used, but an optical recording medium was prepared in the same manner as in Example 17.

Each of the optical recording media obtained in this way was first given 25
After uniformly and sufficiently irradiating the recording layer with 4 nm ultraviolet rays to make the recording layer completely blue, optical recording was performed in the same manner as in Example 1,
This was evaluated. Table 4 shows the evaluation of the recorded results.

Examples 20 to 24 Instead of the diene compound salt represented by compound AIILI,
Example 1 except that diene compound salts represented by compounds A3, 11.12.15 and 20 were used, respectively.
An optical recording medium was prepared in the same manner as in Example 9. Each of these optical recording media was first uniformly and sufficiently irradiated with 254 nm ultraviolet rays to form a blue film in the recording layer, and then optical recording was performed in the same manner as in Example 1 and evaluated. Table 4 shows the evaluation of the recorded results.

[Brief explanation of drawings]

FIG. 1 is a schematic cross-sectional view illustrating one aspect of the structure of an optical recording medium used in the method of the present invention, FIGS. 2 and 3 are schematic cross-sectional views of the optical recording medium illustrating the optical recording process of the present invention, FIG. 4 is a schematic cross-sectional view illustrating one embodiment of the structure of an optical recording medium used in the method of the present invention in which the recording layer is formed of a monomolecular film;
The figure is a schematic cross-sectional view illustrating an embodiment of the structure of an optical recording medium in which a recording layer is formed of a monolayer cumulative film. l:''^ board 2: recording layer 3: light irradiation (recording) part 4: laser beam 5: bit 6: diene compound salt 7: diacetylene derivative compound

Claims (1)

[Scope of Claims] 1) A polydiacetylene derivative compound and the following general formula (1)
) or (2) and a step of irradiating an optical recording medium having a recording layer containing one or more of the compounds represented by (2) with light according to recorded information to form pits consisting of concave portions in the recording layer. An optical recording method characterized by comprising: 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 represents an alkyl group or a substituent. Represents a phenyl group or styryl group that may have R^2 and R^
6 represents an arylene group which may have a substituent that forms a conjugated double bond system with two adjacent -CH=CH- groups, and R^3 and R^7 have a substituent. R^4 represents an alkoxy group, R^5 represents an alkyl group, and A represents an anionic residue. )