JPH0482895A - Dithiolene type organic metal complex, preparation thereof, benzoin compound and benzyl compound - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (one of R<1>, R<2> is octadecyloxy, the other is H, halogen, alkyl, alkoxy; one of R<3>, R<4> is octadecyloxy, the other is H, halogen, alkyl, alkoxy; M is Ni, Pd, Pt). EXAMPLE:Bis(4-n-octadecyloxy-4'-chloro-dithiobenzyl)nickel. USE:A recording material for recording media. PREPARATION:A benzoin compound of formula II (one of R<5>, R<6> is octadecyloxy, the other is H, halogen, alkyl, alkoxy) or a benzyl compound of formula III (one of R<7>, R<8> is octadecyloxy, the other is H, halogen, alkyl, alkoxy) is reacted with a phosphorus sulfide and subsequently with the halide of a metal such as nickel, palladium or platinum or a potassium metallic acid halide.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a dithiolene-type organometallic complex, a method for producing the same, a benzoin compound, and a benzyl compound.

[Conventional technology]

Conventionally, dithiolene-type organometallic complex derivatives include bis(4-dimethylamino-dithiobenzyl)nickel, bis(4-diethylamino-dithiobenzyl)nickel,
Bis(4-dimethoxy-dithiobenzyl)nickel, bis(It2-dithiopher-1-)nickelute 1-ra n-butylammonium, bis(4-methyl-1,2
-dithioferrate)nickel-tetra-n-butylammonium, bis(3,4,5,6-tetramethyl-
to 1,2-dithiophel-1) nickel-tetra-n-
Butylammonium-11, bis(3,4,5゜6-tetrachloro-1,2-dithioferto)nickel-tetra-〇-butylammonium, etc. are known, and these absorb in the oscillation wavelength region of semiconductor lasers. Because of this, it is used as an organic recording material for optical disks (Japanese Patent Application Laid-Open No. 57195336, etc.). In addition, since this complex acts as a -heavyt oxygen quencher, it is used as an additive to improve the light resistance of recording materials with poor stability such as cyanine dyes (JP-A-59-1
85694, etc.). In recording media using these organometallic complexes, recording was performed using a hole punching method using the Hee I mode, but in order to support faster recording speeds, recording media with even higher sensitivity are desired. It will be done.

[Problem to be solved by the invention]

When using the conventionally known dithiolene-type organometallic complex for recording by the above-mentioned hole punching method, it is conceivable to make the recording layer containing the complex thinner in order to increase the sensitivity. , the absorbance or reflectance decreases,
A sufficient S/N ratio cannot be obtained during reading.

In contrast, the present inventors have discovered a novel dithiolene-type organometallic complex whose association state or orientation state changes with heat, thereby changing the absorption spectrum or reflection spectrum of the film. We believe that this will solve the above problems.

Therefore, the present invention provides such a novel dithiolene-type organometallic complex, a method for producing the same, and a benzoin compound and a benzyl compound as raw materials thereof.

[Means to solve the problem]

The dithiolene-type organometallic complex in the present invention has -formation (
I) (In the formula, one of R1 and R2 represents an octadecyloxy group, the other represents hydrogen, halogen, an alkyl group, or an alkoxy group, and one of R3 and R4 represents an octadecyloxy group, The other is hydrogen, halogen, alkyl group or alkoxy group, M is Ni, Pd or pt).

Such dithiolene-type organometallic complexes include bis(
4,4'-di-n-octadecyloxy-dithiobenzyl)nickel, bis(4-n-octadecyloxy-dithiobenzyl)nickel, bis(4-n-octadecyloxy-4'-chloro-dithiobenzyl) ) Nickel, screws (4
-n-octadecyloxy-4'-methyl-dithiobenzyl)nickel, bis(4,4'-di-n-octadecyloxy-dithiobenzyl)palladium, bis(4n-octadecyloxy-dithiobenzyl)palladium, Screw (4
-n-octadecyloxy-4'chloro-dithiobenzyl)palladium\, bis(4-n-octadecyloxy-4
'-Methyl-dithiobenzyl)palladium, bis(4,
4'-di-n-octadecyloxy-dithiobenzyl) platinum, bis(4-n-octadecyloxy-dithiobenzyl) platinum, bis(4-n-octadecyloxy-4'talorodithiobenzyl) platinum, Examples include bis(4-n-octadecyloxy-4'-methyl-dithiobenzyl)platinum.

The dithiolene-type organometallic complex can be produced by reacting a benzoin compound or a benzyl compound with phosphorus sulfide and then reacting a metal halide of nickel, palladium, or platinum or a potassium metal halide.

The above-mentioned benzoin compound has the general formula (ff) H○ (Onaka, one of R5 and RG represents an octadecyloxy group, and the other represents hydrogen or a halogen.

This is a compound represented by an alkyl group or an alkoxy group).

The above benzoin compounds include 4,4'-di-octadecyloxybenzoin, 4-n-octadecyloxybenzoin, 4-n-octadecyloxy-47-chlorobenzoin, 4-n-octadecyloxy-4' -Methylbenzoin, etc.

Further, the above-mentioned benzyl compound is a compound represented by the general formula (I (in the formula, R5 and R6 are the same as in the general formula (II)).

The above benzyl compounds include 4,4'-di-octadecyloxybenzoindecyloxybenzyl, 4-n-octadecyloxy4'-
Examples include chlorobenzyl, 4-n-octadecyloxy-4'-methylbenzyl, and the like.

The dithiolene type organometallic complex is described in the Journal of
The American Chemical Society (Jouna)
], of the American Chemistry
al, 5ociety) Volume 87, 3583-3592
Schroutzer (I965)
It can be manufactured according to the method of Auzer et al.

That is, the benzoin compound represented by the general formula (n) or the benzyl compound represented by the general formula (III) is added to an excess amount (particularly about 1.5 times the mole of the compound) of p2.
s.

After refluxing in an organic solvent such as dioxane with (N H4)2 S○7I as necessary to produce a thiophosphoric acid ester corresponding to the above compound, about 1/2 of the above compound O○ A dithiolene type organometallic complex can be obtained by adding molar amount of a metal halide or potassium metal halide and refluxing the mixture.

As the metal halide compound, nickel chloride (NI
CQ2), palladium chloride (P d CQ2).

There are metal chlorides such as platinum chloride (PtCQ2), and the potassium metal halides include potassium chloroplatinate (K2P t c R4), potassium chloride nickelate (K2N i CQ4), and potassium chloride palladate (K2PclCQ). , ), etc., and such metal halides or potassium metal halides may be hydrates.

The dithiolene type organometallic complex obtained in this way is
After the reaction, a precipitate is produced, which can be purified by washing with acetone or the like and recrystallizing it from ethyl acetate or the like.

The benzoin compound represented by the general formula (II) can be obtained by subjecting a benzaldehyde compound to benzoin condensation in the presence of an alkali cyanide.

As the benzaldehyde compound having the following structure, 4-octadecyloxybenzaldehyde and other benzaldehyde compounds are used in combination. In the general formula (TI), when producing a benzoin compound in which only one of R" and R"' is an octadecyloxy group, it is recommended to use approximately equal moles of p-octadecyloxybenzaldehyde and other benzaldehyde compounds. preferable. In general formula (I1), when producing a benzoin compound (4,4'-di-octadecyloxybenzoin) in which both R5 and R6 are octadecyloxy groups, P-octadecyloxybenzaldehyde and other benzyl Preferably, the amphipathic compounds are reacted at a molar ratio of 90/10 to about 5015°C. In this case, if only 4-octadecyloxybenzaldehyde is used as a raw material, the reaction will not proceed.
Concomitant use of other benzaldehyde compounds is essential. Other benzaldehyde compounds include benzaldehyde,
4-Halobenzaldehyde such as 4-chlorobenzaldehyde, 4-bromobenzaldehyde, 4]O methylbenzaldehyde, 4-ethylbenzaldehyde, 4-propylbenzaldehyde, 4-butylbenzaldehyde, 4-pentylbenzaldehyde, 4-octylbenzaldehyde, 4-decyl Benzaldehyde, 4
-4-alkylbenzaldehyde such as dodecylbenzaldehyde, 4-methyl-xybenzaldehyde, 4-ethylbenzaldehyde, etc.
4-Alkoxy other than 4-octadecyloxybenzaldehyde, such as oxybenzaldehyde, 4-propoxybenzaldehyde, 4-butylhexybenzaldehyde, 4-octyloxybenzaldehyde, 4-decyloxybenzaldehyde, 4-dobutyloxybenzaldehyde, etc. Among benzaldehydes, 4-alkylbenzaldehyde and 4-alkoxybenzaldehyde are preferably those in which the alkyl group or the alkyl group in the alkoxy group is a lower alkyl group, and as the alkyl group becomes larger, benzoin condensation becomes difficult to proceed. It is preferable to use other benzaldehyde compounds together.

As a benzaldehyde compound, two or more types as mentioned above.
Since two or more products are used in combination, two or more types of products will be contained in the reaction solution, but the target compound can be isolated by appropriate purification means. For example, 4,4'-di-octadecyloxybenzoin can be precipitated and separated by cooling the reaction solution, and 4,4'-di-octadecyloxybenzoin precipitated from this reaction solution can be separated. After concentrating or drying the remaining liquid, by recrystallizing from ethanol etc., R5 and R
A benzoin compound in which only one of 6 is an octadecyloxy group can be separated.

In addition, the reaction solution was poured into a saturated l-lium chloride aqueous solution, and the precipitated solid was recrystallized from ethanol etc. (first recrystallization) to separate the precipitated 4,4' di-octadecyloxybenzoin. By concentrating or drying the remaining liquid and recrystallizing it from ethanol or the like, it is possible to separate a benzoin compound in general formula (II) in which only the - side of R5 and R6 is an octadecyloxy group. In addition, by subjecting the concentrated substance of the reaction liquid or the solid that precipitates when the reaction liquid is poured into a saturated aqueous solution of chloride to column chromatography using a packing material such as silica gel,
The desired product can be fractionated.

In the above benzoin condensation, the alkali cyanide includes potassium cyanide, sodium cyanide, etc., and is used in a catalytic amount, preferably in an equimolar or approximately equimolar amount to the benzaldehyde compound. Also, the reaction is
The reaction is preferably carried out in a polar solvent such as N,N-dimethylformamide, N,N-dimethylace1-amide, dimethylsulfoxide, methanol, or ethanol, and water may be added if necessary. The reaction temperature is 40-1.00
°C is preferred.

The benzyl compound represented by the general formula (III) can be produced by oxidizing the benzoin compound represented by the -formation (II). The oxidation method is a method of heating the above-mentioned benzoin compound in a pyridine solution of copper sulfate (the amount of copper sulfate used is preferably equal to or more than 2 times the mole of the benzoin compound, and particularly preferably about 2 times the mole).
, a method of heating in the presence of nitric acid (the amount of nitric acid used is preferably equal to or more than the mole of the benzoin compound, particularly preferably about 3 times the mole), a method of heating in the presence of ammonium nitrate (use of ammonium nitric acid) The amount is preferably equal to or more than the mole of the benzoin compound, particularly preferably about 3 times the mole.Also, it is preferable that a small amount of copper acetate be present as a catalyst), a method of stirring in a dimethyl sulfoxide-acetic acid mixed solvent at around room temperature. etc. In these methods, the product can be purified by methods such as recrystallization.

Furthermore, in - formation (TIT), a benzyl compound in which R5 and RG are alkoxy groups can be produced by a method characterized by reacting an alkali metal salt of 4,4'-dihydroxybenzyl with an alkyl halide. can.

The alkali metal salt of 4,4'-dihydroxybenzyl has the structure 4,4'-dihydroxybenzyl and 3. ,
Alkali metals such as Na, K, ■, jH, Na
H.

Alkali metal hydrides such as KH, LjOH.

It can be obtained by reacting with an alkali metal hydroxide such as NaOH or KOI-I. It is preferable to use the alkali metal, its hydride, or its hydroxide in an amount of at least twice the mole of 4,4' dihydroxybenzyl. As the alkyl halide, octadecyl halides such as octadecyl chloride, octadecyl bromide, and octadecyl iodide are used as an essential component, and other alkyl halides are used in combination as necessary. Other alkyl halides are preferably used in an amount of 50 mol % or less based on the total amount of alkyl halides. Furthermore, when two or more types of alkyl halides are used in combination, the order of addition is arbitrary. The alkyl halide is preferably used in equimolar or approximately equimolar amounts relative to 4,4' dihydroxybenzyl. The above reaction is N.

The reaction is preferably carried out in a polar solvent such as N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, and the reaction temperature is preferably 40 to 70°C. The desired product can be purified by a method such as recrystallization, or can be fractionated and purified by column chromatography using a packing material such as silica gel.

The dithiolene-type organometallic complex described above is formed into a film on a substrate by various methods, and when thermal energy such as laser light is applied to the film of the complex, the association state or orientation state of the complex in that part changes, causing light absorption. The spectrum changes. Utilizing this phenomenon, a film of the above complex can be used as a recording material.

Methods for forming a film from the above complex include a method in which a solution of the complex and, if necessary, a polymer is dissolved in an organic solvent is spin-coated, a vacuum evaporation method, a Langmuir-Prodgett method (L
Method B) etc.

Among these methods, if the Langmuir-Blodgett method (LB method) is used to form a film, a homogeneous film without defects such as pinholes can be obtained, which is advantageous for thinning the film, and furthermore, it is possible to control the orientation state of molecules to some extent. .

As the substrate, inorganic glasses such as quartz glass and silicate glass, and plastics such as polymethyl methacrylate resin, polycarbonate resin, and epoxy resin are used. It is preferable to form a group on the board in advance for the 1-ranking servo. In addition to the above substrate and recording film, a reflective layer and a protective layer are added as necessary.

A heat insulating layer or the like may be provided. Furthermore, if the recording film is sandwiched between substrates having transparent electrodes and, if necessary, an alignment film, it becomes possible to control the orientation of the recording film using an electric field, and it also becomes possible to erase the recording.

The polymer used as necessary in spin coating may be any polymer that is compatible with the dithiolene type organometallic complex, and specifically, polymethyl methacrylate, polymethyl methacrylate,
Polybutyl methacrylate-1, polycyclohexyl methacrylate-1, polystyrene, polyvinyltoluene, poly tert-butylstyrene, and the like can be mentioned. The mixing ratio of the dithiolene-type organometallic complex and the polymer is desirably as low as possible in order to suppress a decrease in optical density due to dilution.

When forming an LB film of a dithiolene type organometallic complex, an amphiphilic film-forming substance having a long-chain alkyl group having about 10 to 24 carbon atoms may be used in combination. Examples of the film-forming substance include fatty acids such as stearic acid, aliphatic alcohols such as stearyl alcohol, and fatty acid esters such as methyl stearate. The mixing ratio of the dithiolene type organometallic complex and the film-forming substance is 1 to 1 in terms of molar ratio of the former to the latter.
:20, but in order to suppress the decrease in optical density due to dilution, it is desirable to use as little amount of the film-forming substance as possible.

〔Example〕

The present invention will be explained in more detail with reference to Examples below.

Example 1 4-Hydroxybenzaldehyde”-6g.

5.7 g of NaOH and 50 g of iodo-n-octadecane were added to N,N-dimethylformamide (hereinafter referred to as DM).
35 g of 4-n-octadecyloxybenzaldehyde was obtained by reacting in 300 mQ (abbreviated as F) at 60° C. for 2 hours. The obtained 4n-octadecyloxybenzaldehyde 25 g (0,065 mol), 4-chlorobenzaldehyde 9.4 g (0,065 mol) and K
Using 3.9 g of CN and 250 mM of DMF as a solvent, the reaction was carried out at 90° C. for 3 hours. Then, the reaction solution was cooled and the precipitated crystals were filtered off, and the crystals were recrystallized from ethanol to obtain 2 g of 4,4'-di-n-octadecyloxybenzoin. The 'H-NMR spectrum and IR spectrum (KBr method) of this are shown in Figures 1 and 2, respectively.
As shown in the figure.

Example 2 7.0 g of 4.4'-di-octadecyloxybenzoin
, P2S, 3.1g and (NH4)2S041.9g
was added to 150 mQ of dioxane and refluxed for 2 hours.

After cooling the reaction solution, excess P2S was filtered off, and the filtrate was injected with N j
A solution of 3 g of CQ2.6H203 dissolved in 50 mQ of water was added and the mixture was refluxed for 2 hours. Cool the reaction solution,
The deposited precipitate was filtered, washed with acetone, and then recrystallized from ethyl acetate to obtain brownish white crystals of the following formula (a
1.5 g of bis(4,,4'-zirooctadecyloxy-dithiobenzyl)nickel of ) was obtained. The thermal decomposition temperature of this is about 250 DEG C., and the H-NMR spectrum and IR spectrum (KBr method) are shown in FIGS. 3 and 4, respectively.

Example 3 20 g (0,053 mol) of 4-n-octadecyloxybenzaltehyde obtained in the same manner as in Example 1 and 5.7 g (0,053 mol) of benzaldehyde were added to KCN3.
DM F in the presence of 1 g in 250 m fl.

The reaction was carried out at 60°C for 3 hours. After the reaction, the reaction solution was saturated with N
a Cω aqueous solution and cooled. The precipitated solid was filtered off and recrystallized from ethanol. The precipitated crystals were separated by filtration, and the filtrate was dried.

The residue was recrystallized from ethanol to obtain 7.3 g of 4-n-octadecyloxybenzoin. iH-NMR of this
The spectrum and IR spectrum (KBr method) are shown in FIGS. 5 and 6, respectively.

Example 4 5.0 g of 4-n-octadecyloxybenzoin.

P2S, 3.5g and (NH4)2SO42, 1g
was added to 150 mR of dioxane and refluxed for 2 hours. After the reaction, excess p2s was filtered off, and the filtrate was added with N i CΩ2.
A solution of 203.7 g of -6H dissolved in 55 mn of water was added and refluxed for 2 hours. The reaction solution was cooled, the generated precipitate was filtered, and the precipitate was washed with acetone, and then filtered with silica gel.
Bis(4-octadecyloxydithiobenzyl)nickel of the following formula (b), which is a greenish-white crystal, is purified by column chroma 1 using a mixed solvent of hexane/chloroform-8/2 (volume ratio)]. 1.1g was obtained. The thermal decomposition temperature of this is about 260°C, and 1H-NM
The R spectrum and IR spectrum (KBr method) are shown in FIGS. 7 and 8, respectively.

(However, in the formula, one of the two X's is hydrogen and the other is an n-octadecyloxy group, and one of the two X's is hydrogen and the other is an n-octadecyloxy group.) Example 5 4-n-
Octadesyloxy-4'-chlorobenzoin 7.7g
I got it. This's ``I-I-NMR Spec 1 HEL and IR
The spectra (KBr method) are shown in FIGS. 9 and 10, respectively.

Example 6 4-n-octadecyloxy-4'-chlorobenzoin 5
．． 0 g, P2S53.3 g and (NH4),
5O42,0g was added to 50 m fl of dioxanco and refluxed for 2 hours. After cooling the reaction solution, remove excess P2S by filtration, and add 203,6 g of NJ, CQ, .6H to the filtrate and 55 g of water
A solution dissolved in mQ was added and the mixture was refluxed for 2 hours. After the reaction, the reaction solution is cooled, the generated precipitate is filtered, and the precipitate is
After washing with hexane, silica gel column chromatography [eluent: hexane/chloroform-7/3 (volume ratio)
0.8 g of his(4-n-octadecyloxy-4'-chloro-dithiobenzyl)nickel of the following formula (c) as green-white crystals was obtained.

The thermal decomposition temperature of this is about 260 DEG C., and the 1H-NMR spectra and TR spectra (KBr method) are shown in FIGS. 11 and 12, respectively.

(However, in the formula, one of the two X3s is chlorine and the other is n-
In the octadecyloxy group, one of the two X4's is chlorine and the other is n-octadecyloxy group. ) Test Example 1 Toluene solution of bis(4,4'-di-n-octadecyloxy-dithiobenzyl)nickel (ImmoQ/Q)
was dropped onto a heat-resistant glass substrate and spin coated. The coating conditions were 400 rpm for 20 seconds, then] 2 Q Orp
+n for 30 seconds. The absorption spectrum of the obtained film is shown as a graph in FIG.

When the obtained film was heated to 80'C in air and then cooled to room temperature in air, the thickest absorption shifted slightly to the longer wavelength side and the absorbance also slightly decreased, as shown in graph 2 in Figure 13. Rose.

When this film was further heated to 125 DEG C. and then cooled to room temperature in air, the absorption maximum shifted to the shorter wavelength side by about 50 nm, as shown in graph 3 in FIG.

Test Example 2 In Test Example 1, bis(4-n-octadecyloxy-dithiobenzyl) obtained in Example 4 was used instead of bis(4,,4,'-di-n-octadecyloxy-dithiobenzyl)nickel.
A spin-coating film was prepared under the same conditions as Test Example 1 except that dithiobenzyl) nickel was used. The absorption spectra 1 to 1 of the obtained film are shown as graph 4 in FIG. When the obtained film was heated in air to 70'C and then cooled to room temperature in air, the absorbance increased and the absorption maximum shifted to the shorter wavelength side by about 50 nm, as shown in graph 5 in Figure 14. 1-Shit. When this film was further heated to 125° C. and then cooled to room temperature in air, the absorption maximum shifted to the longer wavelength side by about 55 nm, as shown in graph 6 in FIG.

Test Example 3 In Test Example 1, bis(4-octadecyloxy-4-chloro-dithiobenzyl) obtained in Example 6 was used instead of bis(4,4'-di-n-octadecyloxy-dithiobenzyl)nickel. ) Test Example 1 except that nickel was used.
A spin coating film was prepared under the same conditions as above. The absorption spectrum of the obtained film is shown as graph 7 in FIG. When the obtained film was heated to 125° C. in air and then cooled to room temperature in air, the absorption maximum shifted to the shorter wavelength side by about 60 nm, as shown in graph 8 in FIG.

Comparative Test Example 1 Test Example 1 except that bis(dithiobenzyl)nickel was used instead of bis(4,4'-di-n-octadecyloxy-dithiobenzyl)nickel in Test Example 1.
A spin coating film was prepared under the same conditions as above. The obtained film was subjected to the same heat treatment as in Test Example 1, but no shift in absorption maximum was observed and no change in absorbance was observed. Furthermore, progress of crystallization was observed as the heating temperature increased.

Example 7 2.0 g of 4.4'-dihydroxybenzyl in DM
Dissolved in F50rnQ, gradually added 0.5 g of helium hydride (containing about 55% liquid paraffin), then added 9.4 g of iodo-ro-octadecane, and heated at 60°C.
The mixture was allowed to react for 2 hours. The solid obtained by cooling the reaction solution was filtered and recrystallized from ethanol to obtain 4,4'-n-octadecyloxybenzyl 2.
．． 2g was obtained. 'I-■-N MR spectra 1 to IR spectra) to IR spectra (KBr method) are shown in FIGS. 16 and 17, respectively.

Obtained 4, 4. 2.0 g of '-di-n-octadecyloxy6-benzyl was used in place of 7.0 g of 4,4'-di-n-octadecyloxybenzoin, and p
z s s , (NH4) SO4 and N i
The amount of Cfl, , 6H20 used is 0.89g each.
, 0.53 g and 0.95 g, and in the same manner, bis(4,,4'-di-n-octadecyloxy-dithiobenzyl)nickel 0
．． 65 g was obtained.

〔Effect of the invention〕

The dithiolene-type metal complex in Claim] is novel, and its association state or arrangement state changes with heat, and its absorption spectrum changes, making it useful as a recording material for a recording medium.

Both the benzoin compound in claim 2 and the benzyl compound in claim 3 are new and useful as raw materials for the dithiolene metal complex.

According to the method according to claim 4, the dithiolene metal complex can be easily produced.

[Brief explanation of the drawing]

Figure 1 shows the 11-I-NMR spectra of 4,4'-di-n-octadecyloxybenzoin obtained in Example 1, Figure 2 shows the IR spectrum of the compound, and Figure 3 shows the IR spectrum of the compound. is 1H-N M of bis(4,4'-di-n-octadecyloxy-dithiobenzyl)nickel obtained in Example 2.
4 is the IR spectrum of the complex, FIG. 5 is the J(-NMR spectrum of 4-n-octadecyloxybenzoin obtained in Example 3, and FIG. 6 is the IR spectrum of the compound. , Figure 7 shows the 'H-N M of bis(4-n-octadecyloxy-dithiobenzyl)nickel.
R spectrum, Figure 8 is the IR spectrum of the complex, Figure 9 is the 1H-NMR spectrum of 4-n-octadecyloxy-4'-chlorobenzene, and Figure 10 is the IR spectrum of the compound. , Fig. 11 shows the 'F(-NMR spectrum of bis(4-n-octadecyloxy-4'-chloro-dithiobenzyl)nickel), Fig. 12 shows the IR spectrum of the complex, and Fig. 13 shows the bis(-NMR spectrum of bis(4-n-octadecyloxy-4'-chloro-dithiobenzyl)nickel). 4゜4'-J-n
-octadecyloxy-dithiobenzyl) nickel absorption spectrum, Figure 14 is the absorption spectrum of bis(4-n-octadecyloxy-dithiobenzyl) nickel, Figure 1
Figure 5 shows the absorption spectra of bis(4r)-octadecyloxy-4'-chloro-dithiobenzyl)nickel, 1st
Figure 6 shows the 1H-NMR spectrum of 4,4'-di-n-octadecyloxybenzyl obtained in Example 7. Figure 17 shows the IR spectrum of the compound. ,.4..7...Absorption spectrum before heat treatment, 2,5
Absorption spectrum after heat treatment at 70"C, 3.6°8...
Absorption spectrum after heat treatment at 125°C. ■

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (However, in the formula, one of R^1 and R^2 represents an octadecyloxy group, The other represents hydrogen, halogen, an alkyl group, or an alkoxy group, one of R^3 and R^4 represents an octadecyloxy group, and the other represents hydrogen, halogen,
A dithiolene-type organometallic complex represented by an alkyl group or an alkoxy group, and M represents Ni, Pd or pt. 2. General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (However, in the formula, one of R^5 and R^6 represents an octadecyloxy group, and the other represents hydrogen, halogen, A benzoin compound represented by an alkyl group or an alkoxy group. 3. General formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) (However, in the formula, one of R^7 and R^8 is an octadecyloxy group, and the other is hydrogen, halogen, alkyl or an alkoxy group). 4. After reacting the benzoin compound represented by the general formula (II) according to claim 2 or the benzyl compound represented by the general formula (III) according to claim 3 with phosphorus sulfide, nickel, palladium or platinum is added. 2. The method for producing a dithiolene type organometallic complex represented by the general formula (I) according to claim 1, which comprises reacting a metal halide or a potassium metal halide.