JPS62503202A - Films and new compounds for them - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Film bodies and new compounds for them It is an object of this invention to provide a substantially inert substrate or support surface and a Consisting of one or several film layers supported thereby, each film A conductive material whose layers are made of organic material that can impart certain electrical properties to the film. The present invention also provides novel chemistries useful for forming film layers in electrically conductive film bodies. It also relates to compounds and intermediates.

The film body according to the present invention can be used for microcircuits, photovoltaic cells, sensors, microphones, small A variety of different electronic applications such as shaped lasers, semiconductor lasers, electrical applications, electrochemistry It can be used for various applications and photochemical applications.

According to British Patent No. 1.572.181 and British Patent No. 1.572°182, A film consisting of several monolayers of organic substances, especially fatty acid derivatives, on top of a substrate. The mu body is well known. The single molecule has a hydrophilic site, a hydrophobic site, and a structure between them. and a cyclic group or acyclic group forming a two-dimensional π-electron system. these The conductive areas of the film body are formed by one single area of each layer. Yes.

Accordingly, the present invention more particularly provides for or by means of a substantially inert substrate surface. consisting of one or several monomolecular film layers of surface-active compounds supported on conductivity, even exhibiting superconductivity at operating temperatures of -40 to +80°C. Regarding a new type of film body whose properties can be selectively changed as desired Ru. The thickness of each film layer is only equivalent to one molecule, and typically 15 to 40 people be. The molecules forming the film layer are liquid crystals. In other words, the optical and electrical properties of the crystal It also indicates the mechanical properties of a liquid. These molecules have a strong tendency to organize Therefore, the degree of molecular orientation within the film layer is extremely high.

Each monomolecular film layer has several regions each parallel to and relative to the substrate surface. sand that is parallel to each other and corresponds to a given location of the organic molecules that form the film layer. It has a switch-shaped structure. The film layer on the one hand is a charge transfer complex (electronic gas generation) on the other hand, consists of a so-called charge transfer (CT) region with groups capable of producing electrically interacts with the charge transfer region of the Polarizable regions with polarizable groups separated by neutral spacer-shaped regions Consists of areas.

Basically, the basic units forming a single film layer are preferably or on the side of larger structural entities such as phosphoglycerol or phosphothreitol. The chain consists of derivatives of fatty acids, aliphatic alcohols, and aliphatic amides.

The film body according to the present invention is formed from phosphoglycerol or phosphothreitol. If two of the hydroxy groups in the glycerol moiety are All three hydroxy groups in the hydroxyl site are oxidized by the above basic aliphatic compound. Tellification, esterification or amidation. The basic aliphatic compound (acid, alcohol , amine) has the above-mentioned charge transfer group and/or polarizable group covalently bonded in the chain. It is a qualitatively aliphatic, long-chain hydrocarbon. two active groups, and by these Basic fatty acids with converted osphoglycerol and phosphothreitol, Alcohol and amine compounds likewise constitute an object of the present invention.

A cross section of the monomolecular film of the above type is shown in the attached FIG. 1.

According to the figure, the single film layer of the illustrated embodiment consists of single parallel regions 2-7. Ru. As mentioned above, each region corresponds to a predetermined site of molecules forming the film.

According to a preferred embodiment, all areas 2 to 7 of the film layers are integral parts. and starting from the support surface 1, in the illustrated embodiment the hydrophilic portion of the molecule It consists of the same organic molecules up to the opposite side, which is 7. According to another preferred similar embodiment If so, the single molecule extends only through regions 3-7 to j2. In this case, the following The surface of the support is pre-coated with a compound corresponding to 7-region 2, as described in detail in It is necessary to do so. Therefore, different molecules or “packed” parallel to each other (pλeked)” in the co-acting part of the side chain that is generally perpendicular to the substrate surface. Each region of the film layer is thus formed. The co-acting parts of different molecules/side chains are supported located substantially the same distance from opposite sides of the surface or molecule.

During the day, the illustrated specific embodiments of the present invention were applied to each molecule/side chain forming the film layer. will be explained while simultaneously referring to the corresponding molecular parts within.

Reference numeral 1 designates the support surface of the film body. The surface of this support is silicon or glass. , constructed of a substantially inert material such as a suitable plastic or metal, and It can be coated with one or several film layers.

The surface of the support is coated by a known method, which will be explained in detail below.

Adjacent to the support surface l is one (2) of so-called spacer regions. This area the chemical properties are substantially inert, and the number of carbon atoms is from 1 to 20, preferably from 4 to 20. 16 aliphatic or substantially aliphatic straight chains that can vary considerably in length or advantageously formed by side chain hydrocarbon groups. This hydrocarbon group is also a chain component It may also contain a heteroatom such as oxygen, nitrogen or sulfur. However, this The presence of such a heteroatom does not materially affect the relatively inert nature of the radical. Insofar as that is the case. Spacer region 2 is the hydrophobic end of the basic aliphatic unit , in a preferred embodiment formed by the outer end of the aliphatic side chain of the phosphatide molecule. be done. However, spacer region 2 is also the material used to precoat the substrate surface. It may also be formed from qualitatively aliphatic hydrocarbons. In order to obtain a more stable structure, this The molecular moiety forming the region exhibits polymerizability, e.g. in the form of double or triple bonds. You can do it like this. In this way, cross-linking with the corresponding part of the side chain of the same molecule or an adjacent molecule can be achieved. structure, for example a polyacetylene structure. Or if this part of the molecule is attached to a group that promotes the attachment of the child to the support surface, e.g. an aromatic (benzene) group. It may have a photoactivatable diazo group.

Region 2 of the film layer has a conductive region of the film adjacent to it in the direction away from the film. come into contact with Overall, this region includes polarizable region 3 (or 5), charge transfer region 5 (or 3) and a spacer region 4 separating them. in this area The extension distance may be 5 to 30 people.

The film layer does not contain polarizable regions and charge transfer regions, and these are spacer regions. The mutual position of these regions is not critical as long as they are separated by shape regions. . Spacer region 4 corresponds to the previously defined region 2 and contains the substance Generally speaking, aliphatic groups are thought to arise from interactions involving corresponding movements in adjacent chains. Ru. Alternatively, the polarizable region may form a kind of buffer region for the charge transfer region. good. Regardless of the reason for the excellent properties, the results from the viewpoint of conductivity are not optimal. , research has shown that it can exhibit superconductivity at high temperatures (300 degrees Fahrenheit).

The electrical properties of the film can be changed or adjusted at two levels. First, in the conductive area By appropriately selecting the groups used, the film can be “tailored” to its intended use. be able to. Second, the final film can be electrically charged, for example by light or an external electric field. Characteristics can be changed.

Adjacent to the conductive areas 3 to 5 of the film again spacer areas of the above type are provided. Ru. This region corresponds to regions 2 and 4 whose structure was defined earlier. against the support surface The outermost film region is a hydrophilic group, such as the phosphoryl group of a phosphatide molecule. Therefore, form. Alternatively, other Polar groups may also be used. Phosphate group on phosphoglycerol or phosphoreitol Depending on the groups contained in the alcohol used to esterify, e.g. The groups contained in the hydrophilic region may be modified so that they exhibit polymerizability in the form of bonds. heavy Typical alcohol esters that exhibit compatibility are polyamide structures with adjacent similar groups. It is serine that forms.

A suitable group or group for forming the molecular portion of the film layer and for use in the charge transfer region. The paired groups are known and can be covalently bonded to substantially aliphatic hydrocarbon groups. As such, any charge transfer pair can be used.

Generally, compounds (or groups) capable of forming charge transfer complexes include, for example, phenyl, naphyl, Bridged or fused aryl having 1 to 6 rings such as thyl, anthryl, and phenanthrene Conjugated cyclic groups and more complex aromatic systems such as pyrene, perylene, and triphenylene It can be characterized as containing a system (π-electrons). These groups or systems are Each can be substituted as appropriate to enhance donor or acceptor properties. suitable Examples of substituents include alkyl (preferably 1-3C), alkoxy (preferably (1-3G), cyano, hydroxy, oxo, amino, substituted amino (e.g. lower (alkyl substitution), thioether groups, etc. Aromatic ring can be any free (unsubstituted) A position can generally contain less than 4 substituents. The cyclic system is also carbazole , phenothiazine, pyrazine, acridine, thianthrene, oxanthrene, te As an integral part of the ring of trathiofulvarene, tetraselenofulvarene, etc. , usually less than 4 and generally up to 2 heteq atoms such as oxygen, silicon, sulfur, and/or or selenium, and metal atoms. According to the present invention, the above click Certain compounds that do not belong to the It has also been proven that A-vitamins that can be formed can also be used.

Typical examples of compounds that can be applied include quinone type groups; Particularly mentioned among these are benzoquinone-hydroquinone pair, and hydroquinone There are forms of anthracene and phenanthrene. Applicable pairs are acceptors and tetracyanobenzene as a donor and tetramethylbenzene as a donor. C Yet another example of a T pair is tetracyanoquinodimethane (TCNQ) and diacyl- and the oxygen of the ester- and ether bonds of the dialkyl-phospholipid. Ma For example, pyrene can also form charge transfer systems with other pyrene groups.

The chemical formulas described on the following pages indicate compounds suitable for use in the charge transfer region.

In some of the chemical formulas, possible attachment positions for the spacer chain are shown. . As already mentioned, the selection of suitable groups is within the skill of the art. Therefore, the present invention should not be considered limited to the groups specified.

le・ Polarizable groups are also known. In fact, applicable CT-groups and polarizable groups are not necessarily distinct. They cannot be separated, and both groups have π-electron and electron donor/acceptor properties. It is characterized by having . Therefore, for the purposes of the present invention, preferred CT-groups are The groups mentioned can also be considered as polarizable groups. Suitable polarizable group Since the selection of the polarizable groups is also within the scope of those skilled in the art, the present invention is not limited to the specified polarizable groups. should not be considered.

However, forming Fthymer and Excibrex, i.e. quantum mechanical waves Groups that share excited electrons are advantageous due to the energy exchange mechanism resulting from functional interactions. It is. Similarly, polarizable moieties include parinaric acid, vitamin A can be diphenyltetradiene and diphenylhexatriene. Ru.

Other groups suitable for the purposes of this invention include those that do not substantially affect the overall properties of the compound. It consists of two heteroatoms, which can be said to be an aromatic group. With these bases mentions in particular the pyrene and perylene groups.

According to one preferred embodiment of the invention, the different regions of the film layer optionally are molecular parts belonging to the same molecule, i.e. supporting film layers, except for the first spacer region. It corresponds to molecules extending from the support surface or conductive region to the outermost region. This embodiment In some cases, the surface of the support is coated with several similar layers to enhance the conductivity of the film body. If it is reversed, it is a smack, and it is also a yuri. Representative compounds used in this layer Examples are phosphoglycerol derivatives, whose substantially aliphatic ethers, amides Alternatively, the ester side chain may be attached at a predetermined distance from the outer end of the side chain (1 to 20C original), depending on the case. has a covalently bonded polarizable group, such as a pyrene group, and glycerol One of the aliphatic side chains of the charge transfer complex pair has a benzoquinone group on the other hand, and The other side chain has a corresponding hydroquinone group.

When the positions of the polarizable group and the charge transfer group in the side chain are reversed, the charge transfer of the above-mentioned strain is improved. The dynamic area can be brought closer to the support surface.

If desired, before coating the support surface, e.g. The surface of the support is treated to improve its surface properties as described in the 0102 specification. may be denatured. As mentioned earlier, such a pretreated surface is further subjected to a first step. A single molecule forming the pacer region may be coated. Additionally, used for pre-coating The conductive regions (3 to 5) of the film layer are formed on the outside of the compound, e.g. It is also possible to provide a covalent member of a cargo transfer pair or a polarizable group. In this embodiment is an aliphatic chain, such as the outermost substantially fatty acid in the aliphatic side chain of phosphoglycerol. an aliphatic hydrocarbon moiety and optionally further the second member of the charge transfer complex pair or Either or both of the polarizable groups may be present in the film to be applied to the surface of the pretreated support. Not present in the forming compound. The essential thing is that, regardless of the manufacturing method, the resulting In the lume layer, the different regions are homogeneous in structure and properties.

In many applications, active groups are added to all aliphatic chains to obtain the desired conductivity. does not have to be covalently included in one of the side chains of a phospholipid, for example. For example, a polarizable group can be included.

form each region necessary to achieve the desired electrical properties of the final film, and a polarizable group and/or a member of a charge transfer pair in a substantially aliphatic hydrocarbon group; A fatty acid, alcohol or amine containing a covalently bonded group can be represented by the following general formula: I can do it.

where the zigzag line has about 1 to 20 carbon atoms, preferably 4 to 16 carbon atoms, and Heterocarbyl groups may be used as long as they do not substantially affect the aliphatic nature of the hydrocarbyl group. Substantially aliphatic straight or branched chain that may contain nitrogen atoms (oxygen, nitrogen, sulfur) means a hydrocarbyl group, A means a member of a charge transfer pair, and B means a polarizable group. Meaning, n.

Bi and q mean O or 1, and Yo is a carboxy group -COOH, hydroxyl group. means a group -OH or an amine group -NH, and further a) n=m=1 and q is 0 or l, or b) n or m is O and q is 0 or is l. In the above definition, any functional derivative is included.

To the best of our knowledge, the above formulas (1a) and (I) containing two active groups (n=m=1) The compounds represented by b) are new and as such constitute the essential part of the invention.

As a compound forming a film layer, two hydroxy groups are of formula (Ia) or of formula Phosphoglycerol substituted with any compound represented by (Ib), or at least two hydroxy groups are represented by either formula (Ia) or formula (Ib) is substituted with a compound corresponding to compound (Ia) or (Ib). , ether or amide bonds are preferred. limits of knowledge In this case, these substituted compounds are novel and constitute an object of the present invention. Ru.

The phosphoglycerol of the present invention is schematically shown as follows.

From AE Engineering In the above formulas (Ila) and (“r’Ib)”, the zigzag line, n2m and The definition of q is the same as in formulas (Ia) and (Ib) above, and A and Ao are charge transfer complexes. B and Bo are the same or different polarizable groups, n'', m' and qo is 0 or l, and Y represents the group -0-1-C(=O)-0- and/or -NH-. To taste, X is hydrogen or an alcohol that forms an ester with a phosphoric acid group, especially lower alkanol, amino lower alkanol, serine, chlorine, l- or 3-glycyl It means the residue of serol. However, n+m and n'+m' are each independently l or 2, and q and qo are each independently 0 or l.

Thus, the compounds of formulas (IIi) and (Ilb) have 1.2 or three spacer groups and one or more active groups, i.e. charge transfer groups and polarizable groups. It has both of these groups, or it has either one of these groups.

If the side chain contains only one or two spacer groups, the pair the third by precoating the substrate surface with a corresponding substantially aliphatic hydrocarbon. A spacer region can be provided. In general formula (IIa), polarizable group B If one or both of and Bo does not exist (n', n=0), or In general formula (Ilb), either CT- group A or Ao is absent In the case (m, m' = O), the substrate is precoated in order to obtain a usable film. The above-mentioned compound to be reversed may not contain the corresponding group. But this The group is used as a mixture with the first described phospholipid with different substitutions. in the side chain with a group or, in some cases, together with the first mentioned phospholipid. The corresponding fatty acids, alcohols or alcohols of general formula (Ia) or (Ib) used themselves may be included in the amine.

The expression “substantially aliphatic°” means “substantially aliphatic” in general formula I and !■. Note that the spacer group may contain non-aliphatic groups as long as they are aliphatic. means. As mentioned earlier, the spacer group is a polymerizable double or triple bond. , and the terminal spacer group contains a contingency group that covalently bonds to the support surface. Good too.

In the different film bodies according to the invention mentioned above, the compounds according to the invention are e.g. For example, the following subclass is a) n=n' = m=m' = 1; q, q' =O or 1° Compounds (Ila) and (Ilb) according to the present invention have about 3 to 60 of substantially aliphatic carbon atoms (corresponding to three spacer groups), or about 2 to 40 Contains either substantially aliphatic carbon atoms (corresponding to the two spacer groups) Substantially aliphatic dialkyl-, diacyl-, diamide-, alkyl-amide- , acyl-amide- or alkyl-acyl-phosphoglycerol. each side chain contains one charge transfer group (A or Ao) and a polarizable group (B or B'). chain If only two spacer groups are present in the Qualitatively fat b) nl and/or n' = O, and m and/or m' = υ. however, n'+m'>0, and n+m>0゜Represented by the general formula (Ila) (Ilb) Each side chain of the compound contains at least one active group. To compound (Ila) and the polarizable group B or Bo, or the charge transfer group A or A in the compound (Ilb) If o is not in the side chain, substituted with polarizable group B° or B or required charge transfer group A° or A The surface of the support is pre-prepared with a compound having a substantially aliphatic chain having 1 to 20 carbon atoms. Can be covered. A mixture of phospholipids with appropriate substituents can be used to achieve the desired polarization. It is also possible to provide functional groups or charge transfer groups.

As already mentioned, the above film layer has at least two (possibly three) side chains. Similarly to the ester, ether or amide bonds of the phospholipids, thread Threito having the above fatty acid, alcohol or amine attached to an itol skeleton This is obtained by using a compound derivative.

The threitol derivative corresponds to the following formula.

0-χ・O-x H〇　-P　=　OEO-P　=　0 (Eng 1 a) (E Ib) In the above formulas (Jl r a) and (TIIb), the zigzag line, n, m, q , n', m', Q', A, A'.

The definitions of B, B', X and Y are the same as in general formulas (IIa) and (11b), n'', m' and q'' mean 0 or 1, A'' means a charge transfer group, and B ' means a polarizable group. However, n+m, n'+m' and n''+m' are Each is independently 1 or 2, but one of these sums must be 0, and q , q' and q'' are each independently 0 or I.

Like glycerol phospholipids, threitol phospholipids also have limited space requirements. It can be used with a precoated substrate that provides a charge transfer group and optionally polarizable or charge transfer groups. same Similarly, when forming the film, suitable e.g. Mixture of glycerophospholipids and/or threitolphospholipids with substituents things can be used. Also, under carefully controlled conditions, the necessary active groups can be a fatty acid, alcohol or amine represented by the general formula (Ia) or (Ib) with A method using glycerophospholipid or threitolphospholipid is also applicable. can.

The above compounds can be produced by methods known per se.

For example, with the desired charge transfer groups and/or polarizable groups, The acyl, amide and/or alkylmino chains can be combined with glycerol or D-mannitol. The compound can be produced by introducing the compound into (M, KateslMethods in Membrane Biolog y, Vol, I3.1977, Plenum Publ, Corp, 219-290). Then, for example, cleavage of substituted D-mannitol.

Reduce to the corresponding glycerol. The substituted glycerol is then placed in the free position. and esterification to introduce a desired phosphoryl group or its derivative.

One of the methods applied to produce 1.2-diacyl-5n-glycerol The method is disclosed in FI-Patent No. 60,700.

In order to introduce a phosphoryl-glycerol group into such compounds, triethylglyceride is used. 1.2 diane-glycerol and phosphorus oxychloride are reacted in the presence of amine. It's fine if you can. Next, the products 1-) to lytyl-s in the presence of triethylamine When reacted with n-glycerol, bospolyglycerol is liberated. Ej bl, H,, Proc.

Na11. Acad, Sci, (197g) p. 40-74, The preparation of sphoryl-ethanolamine and -chlorine is described.

The film body according to the invention can be coated using, for example, the Langmuir-Prodgett coating method. It can be manufactured using conventional methods. The basis of this technique is the surface on which the film is formed. The active compound, e.g. phospho- or sulfolibide, is added to the interface between two layers, e.g. At the interface between (water, glycerol, etc.) and air, argon, etc. The hydrophilic part of the molecule is oriented in the direction of the liquid, and the hydrophobic part is oriented in the direction of the liquid. The objective is to orient the lipophilic part in a direction away from the liquid. desired compound The substance or mixture of compounds may be dissolved in a suitable organic solvent or solvent mixture, such as chloroform or is dissolved in cyclohexane. For example, such The solvent evaporates rapidly from the film made from the solution. Formation on the surface of the support is fed through the interface, preferably at a constant speed, to form a monomolecular film on the surface of the support. Migrate as a layer. In this case, the film forms through the film in the direction from the air to the water. When the adult is delivered, the lipophilic part migrates towards the support surface and moves in the opposite direction, i.e. When the film-forming body is sent through the film in the direction from water to air, the hydrophilic part Migrate towards the support surface. In sending the film forming body several times through the film Thus, virtually any number of film layers can be coated on the surface of the support. Of course It is possible to coat a substrate with several layers of film, each consisting of a different organic material. Both are possible.

What you need to be careful about with regard to chemical structures is that the run at the liquid/gas interface Fatty acids, alcohol, The solubility of amines and their derivatives is often very low. To the present invention According to For example, when three chains are introduced into threitol, the resulting compound is e.g. Easily soluble in roform and thus easily as a monolayer on the water surface with controlled compaction It was discovered that it can be expanded to This is a Langmuir film on the surface of a solid substrate. This is a necessary condition for producing jet film.

The film body obtained by the present invention can be used as it is. or , for example using light or heat. Or even better, depending on the intended use. The surface of the support may be bonded in a suitable manner, either as a whole layer or in parts. You can also let After this, the unpolymerized or unbound portions are removed by a suitable method, e.g. by dissolution. Upon removal, a conductive region with a desired shape can be obtained. One suitable use is as an example An example is microlithography, which uses a laser or electron beam to print onto a film. loading the cyclocycle to promote polymerization and/or bonding to the surface, then removing the untreated portion. remove.

The best method for measuring the electrical conductivity of the compounds according to the invention in film bodies is the so-called four-point measurement system. This is the method used. According to this method, metal, A conductive electrode, eg gold, is eg vacuum deposited. The film is layered directly onto the substrate surface. can be done. Alternatively, by alkylation or in the applicant's international patent application By the method described in PCT/F185100102, the substrate surface may be made hydrophobic. In this case, a monolayer must be formed from one type of molecule. Bye. However, from the viewpoint of conductivity, the best option is to use a mixture of two different acids. Instead, these acids are linked together through a common glycerol structure, creating a type of It has a structure consisting of phospholipids. A voltage is applied between the outermost electrodes, and a voltage is applied between the outermost electrodes. Measure the conductivity of the film body as a flowing current. Typical examples of measured values are: For example, even when not doped with iodine vapor, 10S/cm=Iμs/am. be.

The frequency dependence of the current is determined depending on the composition of the film.

The energy band and energy conditions (state) of the film are tJV and visible region, and the absorption of electromagnetic radiation in the IR frequency range. Wear. For conduction measurements carried out in the optical and UV range, quartz is usually used as the substrate. There is a need to. In some cases, fluorescence emission, excitation spectra, and exciton Relationship of fluorescence emission to time to evaluate information, exciton to film It is also possible to obtain incidental information about the diffusion of ions and the influence of external electric fields.

The invention is illustrated by the following examples.

68 g of salt in a flask of l-hexadecanoyl-2,5-dimethylbenzene IQ hexadecanoyl, 41 m12 of p-xylene and 250 m12 of 1,2-di Added chloroethane. Cool the mixture in water and add about 2 g of 50 g of aluminum chloride. I added one. The mixture was mixed in a water bath for 1.5 hours and at room temperature for an additional 1.5 hours.

The reaction mixture was poured into a mixture of ice and hydrochloric acid. Separate the bottom layer in a funnel until neutral Washed with water, saturated sodium bicarbonate, and water. This was evaporated to dryness and 400m12 of ethanol and 400 m of 2-propanol I set it. 81 g (95% of theory) of crystals were obtained. Melting point: 47-50°C.

81 g of 1-hexadecyl-2,5-dimethylbenzene was added to the flask. Decanoyl-2,5-dimethylbenzene was dissolved in 250ml of acetic acid and 90ml of Added along with hydrochloric acid (37%). Warm the reaction mixture until dissolved and add 6.4 g of 85 g of zinc powder, which had been amalgamated with mercury chloride (11), was added. blend was boiled for 1 hour and cooled. Add 250m (!) of water and use a funnel to make 600m12 Extracted with toluene. The toluene solution was mixed with water and 100ml of 0.5M sodium bicarbonate. Washed with thorium solution and then with water. Sodium sulfate is dried and evaporated to dryness. , 90 g of residue was obtained. Thin layer chromatography (hexane/ether 1 9:1. It was pure according to Rf=0.84). Therefore, leave this as is It was used in the next step.

Methyl 4-hexadecyl-2,5-dimethylphenyl-6-kedohexanoate ether 120, m(!) of 1,2-dichlorobenzene with 1-hexadecyl-2,5-dimethyl Thilbenzene (70g) was dissolved. hexanoic diazid (hexan) oic diacid) methyl ester chloride to 100 m (1.2- Add to dichloroethane and while stirring in a water bath, add 42.3 g of aluminum chloride. was added little by little. Stir the mixture in a water bath for 1.5 hours and at room temperature for 1.5 hours. did. The reaction mixture was added to a mixture of 250 m12 ice and 110 mff 0.5M hydrochloric acid. I poured it. The mixture was extracted with 400ml dichloromethane, water, 160rrl of saturated sodium bicarbonate and water. Dry with sodium sulfate and evaporate the solvent. After evaporation, a residue was obtained which was recrystallized from 700 mQ of ethanol.

24 g of product with a melting point of 51 DEG -55 DEG C. were obtained. Thin layer chromatography (petroleum ether/acetone 9: 1. Rf=0.75), the product is pure. Ta.

4-Hexadecyl-2,5-dimethylphenyl-hexanoic acid methyl ester Add 4-hexane to 60 rrl of acetic acid and 25 ml of 37% hydrochloric acid solution with heating. Dissolve decyl-2,5-dimethylphenyl-6-kedohexanoic acid (24g) did.

21.6. amalgamated with 1.6 g of mercury chloride. of zinc powder was added. solution Boiled for 1.5 hours and then cooled. 70mQ of water and 400m12 of toluet added. Separate the toluene layer, add water, 50 m(!) 0.5 M sodium bicarbonate , and finally washed with water. The mixture was dried over sodium sulfate and evaporated to dryness. . Crystallized first from 150 mff of ethanol, then from 80 mf2 of ethanol. Then, 7.4 g of crystals with a melting point of 50 to 52°C were obtained. Confirmed by NMR , the product showed the desired structure. In the aromatic part, 6. Singlet in sppm 2 oxygen atoms and aromatic-bonded methyl appearing as a singlet at 2.2 ppm There is a base.

4-hexadecyl-2,5-dimethylphenyl-hexanoic acid While heating, diethylene glycol (5 The ester obtained in the above step was dissolved in 0 ml (0 ml). Heat the mixture in a water bath for 1 hour. It was hot. Pour the reaction mixture into a mixture containing 50 g of ice and 12 ml of concentrated hydrochloric acid. is. 160m12 of ether were added. Wash the ether layer until it becomes neutral and add sulfur. dried with sodium chloride. When crystallized from ethanol of 60m(!), the melting point is 7. 5.8 g of crystals with a temperature of 3-75°C were obtained. This acid is used to produce phospholipids. used.

In a 3Q flask, 207 g of 1,4-dimethoxybenzene, 290 ml of chloride Decanoyl and 1.2Q of 1,2-dichloroethane were weighed and charged. Stir with ice While stirring, 280 g of aluminum chloride was gradually added. 1. Pour the mixture in a water bath. Stirred for 5 hours and then at room temperature for 4 hours. Pour the reaction mixture into a mixture of ice and hydrochloric acid , IQ of dichloromethane was added. The organic layer was soaked in 500 mL of water until neutral. 0.5M of sodium oxide, 200M of 0.5M hydrochloric acid, and washed with water. did. The mixture was dried over sodium sulfate, evaporated to dryness and chromatographically analyzed. and purified. Silica was used in an amount of 3 kg and the eluent was petroleum ether/ethyl acetate. Tate 19:1. The obtained 350 g of oily product was directly used in the next step. used.

1. Into a flask of 4-dimeotoxy-2-decylbenzene 3Q, add 350 g of 1 ．． 4-dimethoxy-2-decanoyl-benzene, 800m+2 diethylene glycol Cole and 183 mg of hydrazine hydrate were added.

The mixture was heated slightly and 266 g of potassium hydroxide was added. Boil the mixture for 3 hours After that, hydrazine hydrate was distilled off. Stop distillation when the temperature reaches 196℃. , and the mixture was allowed to cool. Pour the reaction mixture into 1.512 g of water and add 350 mg of 37% Hydrochloric acid solution was added. The product was extracted with 1.8% ether. The product was extracted with silica 3 chromatography column. The eluent is petroleum ether/ethyl ether. Cetate was 98:2. According to NMR, 128 g of the obtained oily product was: This was the desired structure.

2Q 7 Lasconi, 128go) 1,4-dameoxy-2-decyl-benzene, 82g of hexanoic diacid-monomethyl ester-monochloride and 500 ml of 1,2-dichloroethane were added. While stirring in a water bath, 92g of aluminum chloride was added. Continue stirring for 1 hour in a water bath and 1 hour at room temperature. I got it. Add the reaction mixture to a mixture containing 650 g of ice and 20 m2 of 37% hydrochloric acid solution. I poured the mixture. For elution, 650 ml of dichloromethane were used. meta Wash the dichloromethane solution three times with 400 ml of a l:3 mixture of alcohol/water and sulfuric acid. Dried with sodium. Evaporate the solution to dryness and crystallize from 950mR methanol. It became. The 169 g of pure product obtained was of the correct structure according to NMR. Ta.

1.4-dimethoxy-2-decyl-phenylhexanoic acid In a 2Q flask, add the product obtained in the previous step (169 g), 800 m Ethylene glycol and 117 mff1 of hydrazine hydrate were added. Add a little solution The mixture was heated and 170 g of potassium hydroxide was added. Boil the mixture for 2 hours and then , until the temperature reached 196°C. After allowing the mixture to cool, add 950 g of ice and A mixture containing 37% hydrochloric acid solution and 225 m (2) was poured. The organic layer was extracted with water and washed with water until neutral. The product ``sodium sulfate'' Dry in a vacuum and evaporate to dryness. 1. When IQ is crystallized from methanol, the melting point is 5. 126 g of crystals with a temperature of 4-55°C were obtained.

This product is used to produce phospholipids and quinone-hexanoic acid derivatives. used.

Example 3 3-carbazole-6-kedohexanoic acid methyl ester 250m1! 10 g of N-(1-carbomethoxypentanoyl)- Added carbazole. 60 mN dichlorobenzene and 8.5 g aluminum chloride added nium. The mixture was heated at 120°C for 6 hours, allowed to cool slightly, and then heated to 120 m ff of methanol was added. Boil the mixture for 10 minutes, add 120 mff of water, 8 0 mQ of 2M hydrochloric acid solution and 300 mQ of ethyl acetate were added. The mixture was Washed with water, 0.05M sodium bicarbonate solution and water. ethyl acetate solution was concentrated to 100 mC and 100 m5 of petroleum ether was added. 6.8g of crystals This was mixed with 100mQ of trichlorethylene and 10m12 of methanol. It was recrystallized by dissolving it in a mixture containing: In the refrigerator, 3.7 g of product crystallized. This product is pure according to thin layer chromatography. (Rf=0.1; Eluent: petroleum ether/ethyl acetate 7: 3).

To a flask containing 500 mg of 3-carbazole-hexanoic acid ethyl ester, The product obtained in the process (3,7 g), amalgamated zinc [50 g zinc powder and 3 ．． 8g mercury(II) chloride, 80mN 37% hydrochloric acid solution and 80ml acetic acid was loaded. Boil for 0.5 hour and filter while hot. 200m12 ethyl Acetate was added and washed with water, 0.5M sodium bicarbonate and water.

After the mixture was evaporated to dryness, it was immediately added with ethanol (200 ml) and sulfuric acid (0, Esterification was carried out by boiling with 5mQ). Concentrate the ester mixture Then, 100 ml of toluene was added, washed with water, and dried over sodium sulfate. mixture chromatography using toluene/ethyl acetate 9:1 as eluent. The residue was purified by chromatography. The purified fractions were combined and crystallized from toluene. . 1.1 g of product having a melting point of IQ3-5° C. was obtained.

If desired, a second hydrocarbon chain may be added to the resulting compound at a symmetrical position.

In a 1e flask, add 100ml of dry toluene and 2g of lithium aluminum. Muhydride was added. While stirring, add 21.4 g of 12-pyrenyl-dodecane. The acid ethyl ester was dissolved in 100mj of toluene and 50mj of tetrahydrofuran. dissolved in a solution containing After the mixture was stirred at room temperature for 1.5 hours, a 30 m A mixture containing tylacetate and 60ml of toluene was added. 120m ( 2M hydrochloric acid was carefully added dropwise. Separate the organic layer and stir until neutral, 80 Washed with mQ of water, 60 mQ of 2M sodium hydroxide and water. Evaporate the mixture to dryness and using toluene/ethyl acetate 9:1 as eluent, 100. Siri It was rectified with Kakaram. The purified fraction was crystallized from 140 ml of toluene. melting point 80-1'C product 14.4. was gotten.

K Bukkaku 1 4-(5-carboxypentyl)-2,3,5,6-tetramethyl-6-ketohene Xanonic acid methyl ester 150ml! of 1,2-dichloroethane, 2,3, 5゜Methyl ethyl 6-titramethylphenylhexanoate (29g) and hexa Dissolve Neuc Diazid monomethyl ester monochloride (23g). Ta. Add aluminum chloride to 46.8 while stirring on ice. 1 hour Afterwards, the mixture was poured into a freeze/hydrochloric acid mixture and 1 g of ether was added. let the mixture stand Then I decanted it. Wash the ether solution with water and dry until neutral. , and evaporated. The residue was chromatographed (330 g silica, eluent TTR). (Ene/methanol 97:3) and crystallized from toluene. melting point is 1 11-. Pure product at 1°C 17.0. was gotten.

This product was converted to the acid chloride using oxalyl chloride and Friedel ・Using the Clach reaction, it was further bonded to an active group.

Example 6 4-(Carbomethoxypentanoyl)-2,4-dimethoxyphenyl-hexano acid 1 (into the flask of 2, add 32.5 g of 2.4-dimethoxyphenylhexanoic acid, 450m1! of 1,2-dichloroethane and 42.2 g of hexanoic dia. Gid's monomethyl ester chloride was added. While stirring on ice, 63 g of aluminum chloride was added and the mixture was stirred for 2.5 hours, then mixed with ice and water. Pour it on things. The organic layer was washed with water four times and evaporated in an evaporator. Residue at 8o.

g Purified using a silica column. Diisopropyl ether of 75m pure distillate (! It was crystallized from. 16.1 g of product with a melting point of 75-70 mm were obtained. Trichloro Using oxalyl chloride in ethylene solution (6 ml) at 70°C for 1 hour. The product was converted to the acid chloride by heating. Finally, evaporate the solvent and obtain The acid chloride obtained was used as received.

4-(pyrenyl-6-kedohexyl)-2,4-dimethoxyphenyl-6-keto Hexanoic acid methyl ester Acid chloride (18 g) from the previous step was added to 60 m (! 1° Dissolved in 2-dichloroethane. 12.0g pyrene, 23.7g salt in ice Aluminum chloride was added. Stir the mixture in ice for 0.5 h and at room temperature for 2 h. did. Pour this into a mixture containing i 80g water and 90m+2 2M hydrochloric acid, Add 120me dichloromethane, water, 0.5M sodium hydroxide, 0.5M Washed with hydrochloric acid and water.

silica using a 9:1 mixture of toluene/ethyl acetate as eluent. The mixture was rectified on a ram. Crystallized from the eluent in the refrigerator, 14.8 g The desired product was obtained.

4-(pyrenylhexyl)-2,4-dimethoxyphenyl-hexanoic acid The product obtained in the previous step (8.4 g) was reduced by the Wolf-Kishchi method. 3.6 g of product with a melting point of 118-118.5°C was obtained.

This product was used for the production of phospholipids, but dimethoxyphenylene oxidizes the quinone moiety to quinone, and then converts the quinone moiety to tetracyano-quinone dimethane. Converted.

The above acids and corresponding acids can be used, for example, in the production of the phospholipids described below. Wear.

1-(valmitoyl)-2-(4-pyrenylhexyl-2,4-dimethoxyphene) nyl-hexanoyl) sn-glycerol-3-phosphocholine 1-decylquinonehexanoyl-2-(4-pyrenylhexyl-2,4-dihyde Roxy-phenylhexanoyl-5n-glycerol-3-phosphocholine 1-( 4-decyltetracyanoquinone dimethanehexanoyl)-2-pyrene-tetrade Kanoyl-5n-glycerol-3-phosphocholine and -3°-glycerol 1 -(4-decyltetracyanoquinonedimethanehexanoyl)-2-tetramethyl -tetraselenofulvalenundecanoyl-5n-glycerol-3-phosphoco Phosphorus and =1'-glycerol and -3°-glycerol 1-pyrenyl octade Kanoyl-2-pyrenylhexylpyrenylhexanoyl-5n-glycerol- 3-phosphocholine 1-Valmitoyl-2-pyrenylhexanoyl-5n-glycerol-3-phos Ho-Io-glycerol and -3°-glycerol I-balmitoyl-2-pyrenyltetradecanoyl-5n-glycerol-3- Phospho-1'-glycerol and -3'-glycerol l-hexylanthracenehexanoyl-2-hexyltetracyanoquinone dimer Tan-sn-glycerol-3-phosphocholine l-Birenyldodecyl-2-decylquinonehexanoyl-5n-glycerol- 3-phosphocholine and -methanol I-pyrenyltetradecanoyl-2,3-di(pyrenylhexanoyl)-L-su Rayitol-4-phosphocholine and -methanol Production examples of the present invention will be explained below using Examples.

Example 7 1-pyrenyldodecanyl-2-decyl-quinonehexanoyl-3-triphenyl Methyl-5n-glycerol (pyrenyldodecanol mesylate and isopropylene) react denglycerol, hydrolyze the isopropylidene protecting group, and free (obtained by protecting the released primary hydroxyl group with a triphenylmethyl group) ! -pyrenyludecanyl-3-triphenylmethyl-5n-glycerol (6 ,0g), decylquinonehexanoic acid (3,7g) and dimethylaminopyridine (210mg) was dissolved in 50ml dichloromethane. 2.1g dicyclo Hexylcarpodiimide was added. The mixture was allowed to react at room temperature for 4 hours, and 50me hexane was added. Filter, add 0.5M hydrochloric acid, water, 0.5M sodium bicarbonate. Washed with thorium and water, dried over sodium sulphate and evaporated. He as an eluent 150g licash using xane/ethyl acetate 99:1 and 98:2 It was purified by chromatography method. Product 7.9 with melting point 35-9°C g was obtained.

1-pyrenyldodecyl-2-decyl-quinone-hexanoyl-5n-glycerol le The product obtained in the previous step (7.9 g) was dissolved in toluene and 150 g boric acid/silica In addition to Kakaram, 500m1! toluene and toluene/ethyl acetate 95 :5 and 90:10. The product was crystallized from ethanol. This is it Thus, 3.7 g of purified product (melting point: 80-1°C) was obtained. This purified product is purified by a known method. It was used to prepare phospholipids by introducing phosphoryl groups.

In a flask, add 4.6g of Shiichithreitol and 23.4g of triphenylmethylchloride. Weighed loride and 50ml of pyridine. Add 100 mff of water and make a water layer. was removed by decantation. Dissolve the mixture in 150ml of toluene , 70ml of 2M hydrochloric acid, water, 0.5M sodium bicarbonate and water. Generate The material was dried over sodium sulfate and evaporated. Toluene/ethyl 1acetate as eluent Tate 9:1 was used. Purified using a 120g silica column. raw obtained 12.9 g of the product was pure according to thin layer chromatography (Rf= 0°39; eluent hexane/acetone 7:3).

1,4-di(triphenylmethyl)-2,3-di(pyrenehexanoyl)-L- slaytall Using 15 m(!) of dichloromethane as the solvent, add 3.0 g of 1. 4-di(triphenylmethyl)-L-threitol and 4.75. Pirenheki of Sanonic acid and 60 mg dimethylaminopyridine were added. Stir the mixture at 30°C Then, 2.6 g of dicyclohexylcarbodiimide was added. 2 of the mixture Stir for 0 hours, filter and wash with 2M hydrochloric acid, water, 0.5M sodium bicarbonate and water. Purified. 100 using toluene/ethyl acetate 99:l as eluent. Purification was performed using g silica column. 2.1 g of the desired product was obtained, in addition to which monopi Lenhexanoyl compound was obtained in an amount of 1.1 g.

This compound can be used to make threitol phospholipids containing three different acids. Ru.

2.3-di(pyrenylhexanoyl)-L-threitol and 1-triphenyl Methyl-2,3-di(pyrenehexanoyl)-L-threitol The product obtained in the previous step (2.1 g) was dissolved in toluene and dissolved in boric acid/silica gel ( 21 g) was added to a chromatography column packed with 21 g). 100ml toluene Elution was performed gradually using Furthermore, toluene/ethyl acetate 95:5 and 90:10. 0.6 g of 2,3-di(pyrenehexyl) Sanoyl)-L-threitol (Rf=0.39: Eluent chloroform/2- propatool 9:l) and 0.34 g of 1-triphenyl-2,3-di(pyrene) hexanoyl)-L-threitol (Rf=0.81, eluent chloroform/ 2prop tool 9:1) was obtained. These compounds are made of glycerophospholipids. can be used to produce threitol phospholipid in a manner compatible with its production.

,,7 F Engineering G, 1 Copy and translation of the written amendment) submission form (calligraphy and painting pursuant to the provisions of Article 184-7, Paragraph 1 of the Patent Law) Commissioner of the Patent Office Black 1) Akio Hitoshi 1. Display of patent application PCT/FI 86100067 2゜Name of invention Film bodies and new compounds for them 3 Patent applicant Address: Republic of Finland, Helsinki Nisev, -00380゜Varimoti D.7 Name: KSB Chemicals Representative: Kinnunen, Paabo Nationality: Republic of Finland 4 agents Address: 752 Marunouchi Building, 2-4-1 Marunouchi, Chiyoda-ku, Tokyo 100 Ward December 1, 1986 AD 6 List of attached documents Amended patent claims 1. Substantially inert support surface supporting one or several monomolecular film layers In a conductive film body consisting of a surface, The film layer is made of a surface-active organic substance having liquid crystal properties, and the lume layer is made of a surface-active organic substance having liquid crystal properties. In the cross section of the film, there are at least the following continuous parallel regions: – Polymerizable, substantially inert to electrical properties and capable of bonding to support surfaces a spacer region (2) which can contain groups; One charge transfer region (3 or 5), polarizable region (5 or 3), and between these regions is substantially inert with respect to electrical properties and can contain a polymerizable group. Conductive regions (3 to 5) consisting of a pacer group (4), -corresponding to the above region (2), a spacer region (6) which may likewise contain polymerizable groups; and - a polymerizable group. having a sandwich structure comprising a hydrophilic region (7), which may include Features a film body.

2. The spacer region (2, 4 and/or 6) has 1 to 20 carbon atoms, preferably contains 4 to 16 substantially aliphatic straight-chain or branched hydrocarbon groups, the groups in parentheses being A patent characterized in that it can contain a double bond or triple bond as a polymerizable group The film body according to claim 1.

3. The charge transfer region (3 or 5) is a quinone derivative as a group forming a charge transfer complex. , especially benzoquinone or anthraquinone groups and the corresponding hydroquinone groups, or A patent claim characterized by containing a tracyanobenzene-tetramethylbenzene pair The film body according to item 1 or 2.

4. The polarizable group has an aromatic hydrocarbon group as a polymerizable group, preferably pyrene and/or According to any one of claims 1 to 3, characterized in that it contains a perylene group. The film body described.

5. The hydrophilic region (7) is a lower alkano group which can be appropriately substituted with a polymerizable group. alcohol, amino-lower alkanol, serine, chlorine or 1°- or 3'-glucanol Items 1 to 4, characterized in that they contain phosphoric acid suitably esterified with a lycerol group. The film body according to any one of the above.

6. Regions (7) to (2) or (3) are represented by the following general formula (IIL) or (Ib) [In the formula, the zigzag line has about 1 to 20 carbon atoms, preferably 4 to 16 carbon atoms, and Heteroatoms (acid Substantially aliphatic straight or branched chain hydrocarbons that can contain 1. Means carbyl group. A means a member of a charge transfer pair, B means a polarizable group , n, m and q mean 0 or 1, and Yo is a carboxy group -C0OH, droxy group -OH or amine group -NH, (where n=m=1, q is 0 or l ), and their functional derivatives]. The film body according to claim 1, characterized in that:

7. Regions (7) to (2) or (3) are represented by the following general formula (■a) or (Ib) [In the formula, the zigzag line has about 1 to 20 carbon atoms, preferably 4 to 16 carbon atoms, and Heteroatoms (acid Substantially aliphatic straight or branched chain hydrocarbons that can contain means a carbyl group, A means a member of a charge transfer pair, B means a polarizable group, n,! n and q mean 0 or l, and Yo is a carboxy group -COOH, Droxy group -OH or amine group -NHt (however, aln=m=1, q is 0 or or b) n or m is 0 and q is 0 or 1), and means a functional derivative], the compound represented by Phosphoglycero in which the xy group is esterified, etherified and/or amidated As set forth in claim 1, the material is made of threitol or -threitol. film body.

8. Phosphoglycerol has the following general formula [wherein the zigzag line, n, m and q are It has the same meaning as stated in claim 7, and A and A' are charge transfer pairs. and B and Bo are the same or different polarizable groups; n', m' and qo means 0 or l, Y is a group -o-, -c<=o)-o- and/or -NH- X means hydrogen, or an alcohol that forms an ester with a phosphoric acid group, especially lower alcohol, amino lower alkanol, serine, chloraine, 1- or 3 - refers to the residue of glycerol, where n+m and n'+m' are each independently 1 or 2, and q and qo are each independently 0 or 1]. The film body according to claim 7, characterized in that:

9. Phosphothreitol has the following general formula (% formula %) [In the formula, zigzag line, n, m, q, n', m', q'.

A, A', B, B', X and Y are the general formula % formula % and The meaning is the same as in Ilb, n"1m" and qo mean 0 or 1, and A ” means a charge transfer group, and B” means a polarizable group h(, n m, n' +m’ and qn “10m” are unrelated Z or 2 (however, these One of the total values may be O), and q, qo, and q'' are each independently 0. or 1, as set forth in claim 7. Lum body.

international search report &lI#l*++kyla*6-1+j+nllNa,FC'+1/FI861 000671″′@′M″eMI A teacher ka1m II″FCT/FI8610 0067

Claims (9)

[Claims] 1. a substantially inert support surface supporting one or several monomolecular film layers In a film body exhibiting conductivity, consisting of The film layer is made of a surface-active organic substance having liquid crystal properties, and the lume layer is made of a surface-active organic substance having liquid crystal properties. In the cross section of the film, at least the following continuous parallel regions: - polymerizable, substantially inert to electrical properties and capable of bonding to the support surface; a spacer region (2) which can contain groups; - Charge transfer region (3 or 5), polarizable region (5 or 3), and between these regions is substantially inert with respect to electrical properties and can contain a polymerizable group. Conductive regions (3 to 5) consisting of a pacer group (4), -corresponding to the above region (2), a spacer region (6) which may likewise contain polymerizable groups; and - a polymerizable group. having a sandwich structure comprising a hydrophilic region (7), which may include Features a film body. 2. The spacer region (2, 4 and/or 6) has from 1 to 20 carbon atoms, preferably contains 4 to 16 substantially aliphatic straight-chain or branched hydrocarbon groups, the groups in parentheses being A patent characterized in that it can contain a double bond or triple bond as a polymerizable group The film body according to claim 1. 3. The charge transfer region (3 or 5) is a quinone derivative as a group forming a charge transfer complex. , especially benzoquinone or anthraquinone groups and the corresponding hydroquinone groups, or A patent claim characterized by containing a tracyanobenzene-tetramethylbenzene pair The film body according to item 1 or 2. 4. The polarizable group is an aromatic hydrocarbon group, preferably pyrene and/or According to any one of claims 1 to 3, characterized in that it contains a perylene group. Film body as described. 5. The hydrophilic region (7) is a lower alkanoyl group that can be appropriately substituted with a polymerizable group. alcohol, amino-lower alkanol, serine, chloraine or 1'- or 3'-glycanol Items 1 to 4, characterized in that they contain phosphoric acid suitably esterified with a lycerol group. The film body according to any one of the above. 6. The general formula below ▲There are mathematical formulas, chemical formulas, tables, etc.▼(Ia)▲There are mathematical formulas, chemical formulas, tables, etc. (Ib) [wherein the zigzag line has about 1 to 20 carbon atoms, preferably 4 to 1 6, as long as it does not substantially affect the substantial fatty character of the hydrocarbyl group. Substantially aliphatic straight or branched chains that may contain teloatoms (oxygen, nitrogen, sulfur) refers to a branched hydrocarbyl group, A refers to a member of a charge transfer pair, and B refers to a polarizable group, n, m and q are 0 or 1, and Y' is a carboxy group -C OOH, hydroxyl group -OH or amine group -NH2 (however, n=m=1, q is O or 1), and functional derivatives thereof] . 7. One-stage formula (Ia) or (Ib) below ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( Ia) ▲Mathematical formulas, chemical formulas, tables, etc.▼(Ib) [In the formula, the zigzag line represents carbon The number of atoms is about 1 to 20, preferably 4 to 16, and the hydrocarbyl group is substantially fatty. May contain heteroatoms (oxygen, nitrogen, sulfur) unless they materially affect the properties. means a substantially aliphatic straight or branched hydrocarbyl group capable of means a member of a charge transfer pair, B means a polarizable group, n, m and q represent 0 or 1. and Y' is carboxy group -COOH, hydroxy group -OH or amine group -NH2 (provided that a) n=m=1 and q is 0 or 1, or b) n or means m is 0 and q is 0 or 1), and their functional derivatives] The compounds shown allow at least two hydroxy groups to be esterified, etherified, etc. from phosphoglycerol or -threitol, which is A surface-active phospholipid characterized by: 8. The general formula below ▲There are mathematical formulas, chemical formulas, tables, etc.▼IIa▲There are mathematical formulas, chemical formulas, tables, etc. ▼IIb [wherein, the zigzag line, n, m and q are as described in claim 7 The meaning is the same, A and A' mean a charge transfer pair, B and B' are the same or different polarizable groups, n', m' and q' mean 0 or 1, Y is a group -O -, -C(=O) -O- and/or -NH-, and X is hydrogen or Alcohols that form esters with acid groups, especially lower alcohols and amino lower alcohols. It means a residue of canol, serine, chloraine, 1- or 3-glycerol. , n+m and n'+m' are each independently 1 or 2, and q and q' are independently 0 or 1]. Glycerol phospholipid according to item 7. 9. The general formula below ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IIIa)▲There are mathematical formulas, chemical formulas, tables, etc. ▼(IIIb) [In the formula, zigzag line, n, m, q, n', m', q', A , A', B, B', X and Y are the general formulas IIa and IIb of claim 8. The meaning is the same as in A, where n'', m'' and q'' mean 0 or 1. '' means a charge transfer group, and B'' means polarizability, but n+m, n' +m′ and n′′+m″ are each independently 1 or 2 (however, these one of the sum values may be 0), and q, q′ and q′′ are each independent 0 or 1]. Do.