Compound, surface treatment agent, and surface treatment method

Abstract

To provide a novel compound suitably used for introducing multiple kinds of different functional groups to a base material in a more convenient manner, a surface treatment agent comprising such a compound, and a surface treatment method.SOLUTION: The invention provides a compound represented by formula (I) in the figure. (In the formula, R1 to R4 are each independently a carboxy group, amino group, or the like; R5 is H or a halogen atom-substituted / unsubstituted C1-6 alkyl group; X is -OCONH-, -OCOS-, or the like; and R6 is an alkylene group if X is not -OCO-, and is a single bond or alkylene group if X is -OCO-.)SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention relates to a compound, a surface treatment agent, and a surface treatment method.

Background Art

[0002] Conventionally, surface treatment agents have been developed that can impart various properties to the surface of a substrate by performing surface treatment by chemical modification.

[0003] In particular, the technique of introducing a functional group at an arbitrary position on a substrate is useful for use as a reaction field in the micro region and for patterning such as color filters and conductive inks. As a technique for introducing a functional group into a substrate, for example, a combination of a self-assembled monolayer (SAM) and photolithography, a microcontact printing method, or the like is used.

[0004] By the way, when constructing an electronic device such as an organic thin film transistor, a technique for forming patterns of a plurality of functional groups is important when producing electrode wiring or performing surface treatment on a portion where a transistor is to be applied. Also, when manufacturing a multifunctional biosensor, it is very useful when introducing a plurality of different functional groups for each portion of the substrate and fixing a plurality of sensor materials using the plurality of functional groups. This is necessary. In order to introduce a plurality of different functional groups for each portion of the substrate in this way, a method of repeating the technique of introducing a functional group into the substrate described above can be mentioned (for example, see Non-Patent Document 1).

Prior Art Documents

Patent Documents

[0005]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] However, in a method of introducing a plurality of different functional groups into a substrate by repeatedly using a technique for introducing a functional group represented by Non-Patent Document 1, the number of processing steps increases, etc., the processing becomes complicated, and the processing time and cost tend to increase.

[0007] The present invention has been made in view of the above circumstances, and an object thereof is to provide a novel compound suitable for use in introducing a plurality of different functional groups into a substrate by a simpler method, a surface treatment agent comprising such a compound, and a surface treatment method.

Means for Solving the Problems

[0008] The present inventors have intensively studied to solve the above-described problems. As a result, they have found that a compound having a predetermined structure can form a stable SAM when used as a surface treatment agent, and have completed the present invention. More specifically, the present invention provides the following.

[0009] (1) A compound represented by the following formula (I).

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[0010] (2) The compound according to (1), wherein R5 is an isopropyl group.

[0011] (3) The compound according to (1) or (2), wherein the functional group generated by light irradiation is not the same as the carboxy group, amino group, hydroxy group or thiol group present in R1 to R4.

[0012] (4) A compound represented by the following formula (Ia).

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[0013] (5) A surface treatment agent containing the compound according to any one of (1) to (3).

[0014] (6) A surface treatment method having at least a surface modification step of forming a chemical bond and modifying at least a part of the surface of a substrate using the phosphate group of the compound according to any one of (1) to (3).

[0015] (7) The surface treatment method according to (6), further having a light irradiation step of irradiating a part of the portion of the substrate modified with the compound with light having a wavelength of 100 nm or more and 400 nm or less after the surface modification step. [Advantages of the Invention]

[0016] According to the present invention, it is possible to provide a novel compound suitable for use in introducing a plurality of different functional functional groups into a substrate by a simpler method, a surface treatment agent composed of such a compound, and a surface treatment method. [Brief Description of the Drawings]

[0017]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Mode for Carrying Out the Invention

[0018] Hereinafter, embodiments of the present invention will be described, but the present invention is not particularly limited thereto.

[0019] ≪Compound≫ The compound of this embodiment is represented by the following formula (I).

Chemical formula

[0020] In formulas (II) to (IX), the left side of the paper is bonded to the benzene ring. In formulas (X) to (XVI), the right side of the paper is bonded to the R6 site, and the left side of the paper is bonded to the C atom of the CHR5 site, respectively.

[0021]

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[0022]

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[0023]

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[0024]

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[0025]

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[0026]

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[0027]

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[0035]

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[0036] The compound represented by formula (I) in this embodiment binds to the substrate through the terminal phosphate group (the terminal on the right side of the paper). On the other hand, the compound represented by formula (I) has a nitrobenzyl group as a functional group (protecting group) that is deprotected by photolysis at the phosphate group and the other end (the terminal on the left side of the paper). Therefore, it functions as a photocleavable coupling agent. In a substrate surface-modified with such a photocleavable coupling material, deprotection occurs only in the portion irradiated with light, and a reactive functional group is exposed at its terminal (the side opposite to the phosphate group bound to the substrate). Specifically, the reactive functional group is an amino group (H2N-) when X in formula (I) is represented by formula (X) or formula (XIII), a thiol group (HS-) when X is represented by formula (XI) or formula (XIV), a hydroxy group (HO-) when X is represented by formula (XII) or formula (XV), and a carboxy group (HOOC-) when X is represented by formula (XVI).

[0037] On the other hand, since deprotection does not occur in the portion not irradiated with light, the nitrobenzyl group remains. And on this nitrobenzyl group, there is a carboxy group, an amino group, a hydroxy group or a thiol group having reactivity different from that of the deprotected terminal, or a group represented by any of formulas (II) to (IX).

[0038] In this way, by modifying the substrate using the compound represented by formula (I), due to having different reactive functional groups in the portion irradiated with light and the portion not irradiated with light by masking etc., a plurality of different functional groups can be easily introduced into the substrate with only one light irradiation. The details of such a process will be described later.

[0039] Further, the compound represented by formula (I) in this embodiment is a phosphonic acid derivative. When used as a surface treatment agent, since the R6 site is an alkylene group, the structure of the compound becomes dense and a stable SAM can be formed, so it has high stability.

[0040] In formula (I), at least one of R1 to R4 is each independently a carboxy group, an amino group, a hydroxy group, a thiol group, or a group represented by any one of formulas (II) to (IX), and the number of such groups can be any one of 1, 2, 3, and 4. Further, when a carboxy group, an amino group, a hydroxy group, a thiol group, or a group represented by any one of formulas (II) to (IX) is present at two or more positions among R1 to R4, the positions where they are present can be any combination among R1 to R4, and they can be the same functional group or different functional groups. Further, when 1 to 3 of R1 to R4 are a carboxy group, an amino group, a hydroxy group, a thiol group, or a group represented by any one of formulas (II) to (IX), the remainder are each independently a hydrogen atom, an alkyl group, a perfluoroalkyl group, or an alkoxy group which may have a perfluoroalkyl group as a substituent, and are not particularly limited as long as they can appropriately adjust the light absorption wavelength of the compound represented by formula (I). These can be appropriately selected to adjust the light absorption wavelength of the compound represented by formula (I).

[0041] Among R1 to R4, among the functional groups other than a carboxy group, an amino group, a hydroxy group, a thiol group, or a group represented by any of the following formulas (II) to (IX), the alkyl group or perfluoroalkyl group may be linear or branched. Also, the number of carbon atoms of the alkyl group is not particularly limited, but when the compound represented by formula (I) is used as a surface treatment agent, if the alkyl group or perfluoroalkyl group is too long, the interaction between the compounds becomes strong and the structure of the SAM becomes dense and stabilized, but conversely, the sensitivity to light irradiation may decrease. That is, from the viewpoint of the balance between the stabilization of the SAM and the improvement of the sensitivity to light irradiation, the alkyl group or perfluoroalkyl group that may be arranged at R1 to R4 is preferably somewhat short. More specifically, the number of carbon atoms of the alkyl group or perfluoroalkyl group that may be arranged at R1 to R4 is preferably 25 or less, more preferably 20 or less, still more preferably 15 or less, even more preferably 12 or less, and most preferably 6 or less. Also, the lower limit of the number of carbon atoms of the alkyl group or perfluoroalkyl group that may be arranged at R1 to R4 is not particularly limited, and may be, for example, 1 or more (2 or more, 4 or more, 8 or more, 10 or more, 15 or more, etc.).

[0042] The alkoxy group as R1 to R4 other than an amino group, a hydroxy group, a thiol group, or a group represented by any of the following formulas (II) to (IX) may or may not have a perfluoroalkyl group as a substituent, as described above. That is, in the present specification, the "alkoxy group that may have a perfluoroalkyl group as a substituent" means that it may be either an alkoxy group having a perfluoroalkyl group as a substituent or an unsubstituted alkoxy group.

[0043] The number of carbon atoms of the alkoxy group as R1 to R4 other than an amino group, a hydroxy group or a thiol group, or a group represented by any of the following formulas (II) to (IX) is not particularly limited. For example, depending on whether the alkoxy group has a perfluoroalkyl group or the number of carbon atoms of the perfluoroalkyl group when it has a perfluoroalkyl group, etc., it can be appropriately set. For example, it may be 1 or more (2 or more, 4 or more, 6 or more, 8 or more, 10 or more, etc.), or may be 25 or less (20 or less, 18 or less, 15 or less, 10 or less, 8 or less, 4 or less, etc.). Further, the carbon chain of the alkoxy group may be linear or branched, but is preferably linear.

[0044] The number of carbon atoms of the perfluoroalkyl group that the alkoxy group as R1 to R4 other than an amino group, a hydroxy group or a thiol group, or a group represented by any of the following formulas (II) to (IX) may have is not particularly limited. For example, depending on the number of carbon atoms of the above alkoxy group, etc., it can be appropriately set. For example, it may be 1 or more (2 or more, 4 or more, 6 or more, 8 or more, 10 or more, etc.), or may be 20 or less (18 or less, 14 or less, 10 or less, 8 or less, 6 or less, 4 or less, etc.).

[0045] When the compound represented by the formula (I) is used as a surface treatment agent, if the perfluoroalkyl group is too long, the interaction between the compounds becomes strong, the structure of the SAM becomes dense and stabilized, but conversely, the sensitivity to light irradiation may decrease. Therefore, from the viewpoint of the balance between the stabilization of the SAM and the improvement of the sensitivity to light irradiation, it is preferable that the total length of the alkoxy groups of R1 to R4 and the perfluoroalkyl group possessed by the alkoxy group is somewhat shorter. More specifically, the total number of carbon atoms of the alkoxy groups of R1 to R4 and the perfluoroalkyl group possessed by the alkoxy group is preferably 25 or less, more preferably 20 or less, still more preferably 15 or less, even more preferably 12 or less, and most preferably 6 or less. Further, the lower limit of the total number of carbon atoms of the alkoxy groups of R1 to R4 and the perfluoroalkyl group possessed by the alkoxy group is not particularly limited, and may be, for example, 1 or more (2 or more, 4 or more, 8 or more, 10 or more, 15 or more, etc.). In addition, the carbon chain of the perfluoroalkyl group that the alkoxy group may have may be linear or branched, but is preferably linear.

[0046] R5 is not particularly limited as long as it is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom as a substituent. However, when the compound represented by formula (I) is used as a surface treatment agent, since it has high stability, when R5 is an alkyl group, if the number of carbon atoms is in the range of 1 to 6, the number of carbon atoms may be appropriately changed according to the purpose. For example, it may be 2 or more (3 or more, 4 or more, 5 or more, etc.), or it may be 5 or less (4 or less, 3 or less, 2 or less, etc.). Further, when R5 is an alkyl group, it may be linear or branched, but when the compound represented by formula (I) is used as a surface treatment agent, since the sensitivity to light irradiation is high, it is preferably branched. When R5 is an alkyl group, it is most preferably an isopropyl group or a t-butyl group. Further, the halogen atom which R5 may have is not particularly limited, and may be, for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. Further, the number of halogen atoms to be substituted is not particularly limited, and the hydrogen atom bonded to the primary carbon may be substituted with 1, 2 or 3 halogen atoms, or the hydrogen atom bonded to the secondary carbon may be substituted with 1 or 2 halogen atoms.

[0047] R6 is an alkylene group when X is a group represented by any of formulas (X) to (XV), and is a single bond or an alkylene group when X is a group represented by formula (XVI).

[0048] The alkylene group in R6 is not particularly limited. For example, the number of carbon atoms may be 1 to 50. However, when the compound represented by formula (I) is used as a surface treatment agent, the longer the alkylene group, the larger the surface area of the alkylene group, the stronger the interaction between the compounds, the shorter the distance between the molecules, and as a result, the compounds can form a denser structure and a highly stable SAM. Therefore, the larger the number of carbon atoms in the alkylene group, the more preferable it is. More specifically, it is preferably 5 or more, more preferably 8 or more, still more preferably 12 or more, and most preferably 16 or more. On the other hand, from another perspective, if the alkylene group is too long, the hydrophobicity becomes strong. Therefore, when a high hydrophilicity is required when used as a surface treatment agent, a shorter one is preferable. For example, the number of carbon atoms in the alkylene group is preferably 40 or less, more preferably 30 or less, and most preferably 20 or less. Also, R6 may be linear or branched, but when the compound represented by formula (I) is used as a surface treatment agent, since the surface area of the alkylene group becomes larger and as a result, it can have higher stability, it is preferably linear.

[0049] X is cleaved by light irradiation to form a reactive functional group. It is preferable that the functional group generated by light irradiation is not the same as the carboxy group, amino group, hydroxy group or thiol group present in R1 to R4. Note that "present in R1 to R4" includes not only the case where R1 to R4 are a carboxy group, amino group, hydroxy group or thiol group, but also the case where Z in formulas (II) to (IX) is a carboxy group, amino group, hydroxy group or thiol group.

[0050] When X is a group represented by formula (XVI), since a carbon atom can be directly bonded to the phosphonic acid, R6 may be a single bond.

[0051] X is not particularly limited as long as it is a group represented by any of formulas (X) to (XVI), and the functional groups of formulas (X) to (XVI) can be selectively used according to the use and purpose.

[0052] In addition, R1 to R4, R5, R6, X, Y, Z, and W in the formulas other than formula (I) in the present specification are the same as R1 to R4, R5, R6, X, Y, Z, and W in formula (I) above.

[0053] ≪Method for Producing Compound≫ [Method for Adding Phosphate Group] The method for producing the compound represented by the above formula (I) of the present embodiment is not particularly limited. For example, after synthesizing the compound represented by formula (5) by the following step (A) or (B), the phosphonate ester moiety in the compound represented by formula (5) is decomposed by step (C) to produce the compound represented by formula (I). The synthesis process is shown below.

[0054]

Chemical Formula

[0055] R8 to R in formulas (2), (4), and (5) 11 are each a carboxy group, an amino group, a hydroxy group, or a thiol group as R1 to R4, or a group represented by any of formulas (II) to (IX), or a carboxy group, an amino group, a hydroxy group, or a thiol group as R1 to R4, or a group represented by any of the following formulas (II) to (IX) that is protected by a protecting group, or a group that is converted into a carboxy group, an amino group, a hydroxy group, or a thiol group as R1 to R4, or a group represented by any of the following formulas (II) to (IX) by treatment such as acid treatment or an organic synthesis process. When R8 to R 11 is a group protected by a protecting group, at least one step of adding a protecting group and a step of removing the protecting group may be provided at an appropriate time before and after (A), (B), and (C). Further, when R8 to R 11 is a group that is converted into R1 to R4 by treatment such as acid treatment or an organic synthesis process, at least one step of converting them at an appropriate time before and after (A), (B), and (C) may be provided. In the following formulas, for the sake of convenience, each functional group on the nitrobenzyl group is denoted as R1 to R4.

[0056] As R7 in formulas (1), (3), and (5), for example, a methyl group, an ethyl group, a trimethylsilyl group, a t-butyl group, or other alkyl groups can be mentioned. These can be appropriately selected as desired. For example, from the viewpoint of facilitating the synthesis of the compound represented by formula (5), R7 is preferably an ethyl group. On the other hand, when obtaining the compound represented by formula (I) finally obtained, since it can be hydrolyzed with a weak acid, it is preferably a t-butyl group, or since it can be hydrolyzed or alcoholyzed under neutral conditions, it is preferably a trimethylsilyl group. Note that R7 in other formulas in this specification is the same as R7 in the above formulas (1), (3), and (5).

[0057] X in formula (3) is any one of a primary amino group, a thiol group, a hydroxy group, or a carboxy group. When X in the finally obtained compound represented by formula (I) is a group represented by formula (X) and formula (XIII), X in formula (3) is a primary amino group. When X in the compound represented by formula (I) is a group represented by formula (XI) and formula (XIV), X in formula (3) is a thiol group. When X in the compound represented by formula (I) is a group represented by formula (XII) and formula (XV), X in formula (3) is a hydroxy group. When X in the compound represented by formula (I) is a group represented by formula (XVI), X in formula (3) is a carboxy group.

[0058] V in formula (4) is either a group represented by the following formula (XVII) or a hydroxy group. When X in formula (3) is any one of a primary amino group, a thiol group, or a hydroxy group, it is preferable to use a group represented by formula (XVII) as V. When X in formula (3) is a carboxy group, V is preferably a hydroxy group.

[0059]

Chemical formula

[0060] The more specific production method of the compound represented by formula (I) of the present embodiment will be described below.

[0061] (Step (A)) In the synthesis method of step (A), for example, after synthesizing a bromide (compound represented by formula (2)) protected in advance with a nitrobenzyl group, a phosphonic acid ester (compound represented by formula (5)) can be synthesized by an Arbuzov reaction (P-C bond formation reaction). Using the compound represented by this formula (5), the compound represented by formula (I) can be produced by step (C).

[0062] As a specific operation of step (A), an operation that causes an Arbuzov reaction (P-C bond formation reaction) can be used. For example, it can be carried out by heating a trialkyl phosphite (trimethyl phosphite, triethyl phosphite, tris(trimethylsilyl) phosphite, etc.), which is a compound represented by formula (1), and the compound represented by formula (2).

[0063] When X is a group represented by formula (X) to (XII), before step (A), for example, by the following steps, a compound represented by formula (2-1) can be synthesized, and using this, a compound represented by formula (5) (in the following steps, a compound represented by formula (5-1)) can be produced.

[0064]

Chemical formula

[0065] The step (a) is an operation for nitrating an aromatic ring, and the specific method can be carried out, for example, by allowing concentrated nitric acid (for example, 70% nitric acid, etc.) to act on the compound represented by formula (6).

[0066] The step (b) is an operation of converting the nitro compound obtained in step (a) into an alcohol by reducing the carbonyl group thereof to synthesize the compound represented by formula (7), and the specific method can be carried out, for example, by sodium borohydride. Further, as the solvent, methanol, THF (tetrahydrofuran), etc. may be used.

[0067] The step (c) is an operation of synthesizing the active carbonate represented by formula (8), and the specific method can be carried out, for example, by reacting the compound represented by formula (7) with di-N-succinimidyl carbonate. Further, as the solvent, TEA (triethylamine), dry acetonitrile, etc. may be used.

[0068] The step (d) is an operation of performing a reaction for synthesizing the compound represented by formula (2-1) having a bromo group at the terminal, and the specific method can be carried out, for example, by reacting the bromide represented by formula (9) with the active carbonate represented by formula (8) using a dried solvent (e.g., dried THF (tetrahydrofuran), etc.) in the presence of triethylamine as a base.

[0069] When X is a group represented by formula (XVI), for example, the compound represented by formula (5) (in the following steps, the compound represented by formula (5-2)) can be produced by the following steps.

[0070]

Chemical formula

[0071] The step (e) is an operation of performing a dehydration condensation reaction between the bromocarboxylic acid represented by formula (9-1) and the alcohol represented by formula (10), and the specific method can be carried out, for example, by using a water-soluble carbodiimide (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, EDC·HCl) as a dehydration condensing agent and N,N-diethylaminopyridine (DMAP) as a base.

[0072] (Step (B)) The synthesis method of Step (B) is not particularly limited. After synthesizing a phosphonate ester (a compound represented by formula (3)) having a functional group of a primary amine, alcohol, thiol, or carboxylic acid at the terminal, a nitrobenzyl group can be introduced into this compound using the compound represented by formula (4), thereby synthesizing the compound represented by formula (5). Using the compound represented by formula (5), the compound represented by formula (I) can be produced by Step (C).

[0073] For the operation of Step (B), an operation of introducing a nitrobenzyl group into the compound represented by formula (3) using the compound represented by formula (4) can be used. Specifically, for example, in the same manner as (d) above, for example, in the presence of triethylamine as a base, the reaction between the compound represented by formula (3) and the compound represented by formula (4) can be carried out using a dried solvent (for example, dried THF (tetrahydrofuran), etc.).

[0074] When X is a group represented by formula (X), including Step (B), for example, the compound represented by formula (I) can be produced by the following method. Also, this synthesis step is the synthesis step when the compound represented by formula (I) is specifically the compound represented by formula (I-1), that is, the synthesis step when R7 is a t-butyl group. When R7 is a t-butyl group, the compound represented by formula (I) which is the final target can be obtained particularly efficiently, so this synthesis step is preferable. The compound represented by formula (4-1) is a compound when V in the compound represented by formula (4) is a group represented by formula (XVII). Note that step (j) in the following method is one step of Step (C) (details will be described later).

[0075] [Chemical formula]

[0076] The step (f) is an operation of performing a reaction to form phosphonic acid by the Arbuzov reaction, similar to the above-mentioned step (A). The specific method can be carried out, for example, by heating triethyl phosphite represented by the formula (1-1) and bromide represented by the formula (11).

[0077] The step (g) is an operation of converting diethyl phosphonate represented by the formula (12) to phosphonic acid represented by the formula (13). The specific method can be carried out, for example, by reacting trimethylbromosilane to convert it to trimethylsilyl ester once, and then by methanolysis.

[0078] The step (h) is an operation of converting phosphonic acid represented by the formula (13) obtained in the step (g) to t-butyl ester represented by the formula (14). The specific method can be carried out, for example, by reacting t-butyl 2,2,2-trichloroacetimidate. As the solvent, for example, dichloromethane or the like can be used.

[0079] The step (i) is an operation of converting phthalimide, which is an intermediate of Gabriel synthesis represented by the formula (14), to amine represented by the formula (3-1). The specific method can be carried out, for example, by hydrazine decomposition of phthalimide. Also, as the solvent, for example, ethanol or the like can be used.

[0080] For the step (j), the method of step (C) described below can be used. For example, dilute hydrochloric acid decomposition can be used. As the solvent, for example, methanol or the like may be used.

[0081] When X is a group represented by the formula (XI), for example, the compound represented by the formula (5) (in the following steps, the compound represented by the formula (5-4)) can be synthesized by the following method.

[0082]

Chemical formula

[0083] For the step (k), the same method as that of the aforementioned step (A) can be used. That is, for the step (k), an operation that causes an Arbuzov reaction (P-C bond formation reaction) can be used. For example, it can be carried out by heating a trialkyl phosphite (trimethyl phosphite, triethyl phosphite, tris(trimethylsilyl) phosphite, etc.) and a compound represented by the formula (9-2).

[0084] When X is a group represented by the formula (XII), for example, the compound represented by the formula (5) (in the following steps, the compound represented by the formula (5-5)) can be synthesized by the following method.

[0085]

Chemical formula

[0086] The step (l) is an operation of introducing a protecting group into the alcohol represented by the formula (9-3) to synthesize the tetrahydropyranyl ether which is the compound represented by the formula (15). The specific method can be carried out, for example, by allowing dihydropyran to act in the presence of an acid catalyst.

[0087] For the step (m), the same method as that of the aforementioned step (A) can be used. That is, for the step (m), an operation that causes an Arbuzov reaction (P-C bond formation reaction) can be used. For example, it can be carried out by heating a trialkyl phosphite (trimethyl phosphite, triethyl phosphite, tris(trimethylsilyl) phosphite, etc.) and a compound represented by the formula (15).

[0088] The step (n) is an operation of removing the tetrahydropyranyl ether which is the protecting group of the compound represented by the formula (16). The specific method can be carried out, for example, by hydrolysis with acetic acid using tetrahydrofuran-water as a solvent.

[0089] When X is a group represented by formula (XIII), (XIV), or (XV), the compound represented by formula (5) can be produced by introducing a nitrobenzyl group into the compound represented by formula (3) in the same manner as in step (B) described above. However, when X is a group represented by formula (XIV), formula (XV), or (XVI), the compound represented by formula (4’) can be used instead of the compound represented by formula (4) described above. The compound represented by formula (4’) is obtained by replacing V in the compound represented by formula (4) with V2. Also, step (o) or step (p) may be performed before step (B). The reaction schemes for producing the compound represented by formula (5) (in the following steps, the compounds represented by formula (5-6), (5-7), or (5-8)) using the specific embodiments of step (B) in this case, namely step (B-1), (B-2), and (B-3), and the pre-steps of these, namely step (o) and step (p), are shown below.

[0090]

Chemical formula

[0091] The above steps (o) and (p) are steps for leading the compound represented by formula (7) to an intermediate (for example, a chloride, bromide, p-toluenesulfonate, etc. such as the compound represented by formula (4’)) for reacting with an amine compound (the compound represented by formula (3-1)), a thiol compound (the compound represented by formula (3-2)), or an alcohol compound (the compound represented by formula (3-3)). More specifically, in step (o), for example, the compound represented by formula (4’-1) can be obtained by reacting the compound represented by formula (7) with phosphorus trichloride or phosphorus tribromide. In step (p), for example, an intermediate represented by formula (4’-2) can be obtained by reacting the compound represented by formula (7) with p-toluenesulfonyl chloride (the compound represented by formula (17)). TsO, which is one of V2, is a group represented by the following formula (XVIII).

[0092]

Chemical formula

[0093] Step (B-1) is an operation of synthesizing a compound represented by formula (5-6) by coupling an amine compound represented by formula (3-1) and a compound represented by formula (4'). The specific method is, for example, after converting the compound of formula (3-2) into sodium amide with sodium hydride, reacting it with the compound represented by formula (4') to obtain the compound represented by formula (5-6).

[0094] Step (B-2) is an operation of synthesizing a compound represented by formula (5-7) by coupling a thiol compound represented by formula (3-2) and a compound represented by formula (4'). The specific method is, for example, after converting the compound of formula (3-2) into sodium thiolate with sodium hydride, reacting it with the compound represented by formula (4') to obtain the compound represented by formula (5-7).

[0095] Step (B-3) is an operation of synthesizing a compound represented by formula (5-8) by coupling an alcohol compound represented by formula (3-3) and an intermediate represented by formula (4'). The specific method is, after converting the compound represented by formula (3-3) into sodium alcoholate with sodium hydride, reacting it with the compound represented by formula (4') to obtain the compound represented by formula (5-8).

[0096] When X is a group represented by formula (XVI), for example, a compound represented by formula (5) (in the following steps, the compound represented by formula (5-2)) can be synthesized by the following method.

[0097]

Chemical formula

[0098] The step (q) is an operation of hydrolyzing the carboxylic acid ethyl ester represented by the formula (18), and the specific method can be carried out, for example, with an aqueous alkali solution in tetrahydrofuran. Thereafter, by passing through step (B), the compound represented by the formula (5) can be synthesized.

[0099] (Step (C)) Step (C) is a method of decomposing the phosphonate ester moiety in the compound represented by the formula (5) to obtain the formula (I), and can be appropriately selected according to the type of R7.

[0100] The step (C) is not particularly limited as long as it is an operation of decomposing the phosphonate ester moiety in the compound represented by the formula (5) to obtain the compound represented by the formula (I), and can be carried out, for example, by acid hydrolysis or alcoholysis after conversion to a silyl ester. From among these methods, an appropriate method can be selected according to the materials used in the synthesis and the properties of the target compound.

[0101] When R7 in the formula (5) is an ethyl group (the compound represented by the formula (5-a) in the following steps), as step (C), the compound represented by the formula (I) can be synthesized by the following step (C-1).

[0102] [Chemical formula]

[0103] The step (C-1) can use the step (C), but is preferably carried out with chlorotrimethylsilane (TMS-Cl) and an alkali metal iodide or bromotrimethylsilane. Also, as the solvent, for example, methanol or the like may be used.

[0104] When R7 in the formula (5) is a trimethylsilyl group (the compound represented by the formula (5-b) in the following steps), as step (C), the compound represented by the formula (I) can be synthesized by the following step (C-2).

[0105]

Chem.

[0106] For the step (C-2) above, the step (C) above can be used, but it is preferably carried out by methanol treatment.

[0107] When R7 in formula (5) is a t-butyl group (the compound represented by formula (5-c) in the following steps), the compound represented by formula (I) can be synthesized by the following steps. Also, if necessary, as shown below, the compound represented by the following formula (5-c) may be synthesized through step (r) and the above-mentioned step (B).

[0108]

Chem.

[0109] The step (r) above is an operation for converting the compound represented by formula (19) into its di-t-butyl ester, and the specific method can be carried out, for example, by treatment with t-butyl 2,2,2-trichloroacetimidate. Also, as the solvent, for example, dichloromethane or the like may be used.

[0110] For the step (C-3) above, the step (C) above can be used, but it is preferably carried out by dilute hydrochloric acid treatment. Also, as the solvent, for example, methanol or the like may be used.

[0111] (Step (D)) Step D is for R8 to R of the compound represented by formula (I) 11When at least one of them is a carboxy group, amino group, hydroxy group or thiol group as R1 to R4, or a group represented by any of formulas (II) to (IX) and the group is protected by a protecting group, deprotection is carried out according to the protecting group. Further, when it is a group that is converted into a carboxy group, amino group, hydroxy group or thiol group as R1 to R4, or a group represented by any of formulas (II) to (IX) by treatment such as acid treatment or an organic synthesis process, a treatment for conversion into R1 to R4 is carried out. Regarding this step, since R1 to R4 are a carboxy group, amino group, hydroxy group or thiol group, or a group represented by any of formulas (II) to (IX), and these functional groups have reactivity, they may be converted into other functional groups by the above steps (A) to (C). In order to prevent this, the reaction route may be appropriately designed, and means such as protecting R1 to R4 or forming the target R1 to R4 after the steps of (A) to (C) may be taken. Hereinafter, specific examples will be described.

[0112] [When R1 to R4 react during the process of terminal phosphorylation] When R1 to R4 react in the steps of (A) to (C) (terminal phosphorylation), as described above, R8 to R in formulas (2), (4), (5) 11 As R1 to R4, a carboxy group, amino group, hydroxy group or thiol group as R1 to R4, or a group represented by any of formulas (II) to (IX) and the group is protected by a protecting group, or a group that is converted into a carboxy group, amino group, hydroxy group or thiol group as R1 to R4, or a group represented by any of formulas (II) to (IX) by treatment such as acid treatment or an organic synthesis process is used. When R8 to R 11 is a group protected by a protecting group, at least one step of adding a protecting group and a step of eliminating the protecting group are provided at an appropriate time before and after (A), (B) and (C). Further, when R8 to R 11 is a group that is converted into R1 to R4 by treatment such as acid treatment or an organic synthesis process, at least one step of converting them at an appropriate time before and after (A), (B) and (C) is provided. More specifically, hereinafter, a method for producing a compound represented by formula (5-9) will be described as an example. [Chemical formula]

[0113] The above step (s) involves treating the compound 1-(4,5-dimethoxy-2-nitrophenyl)-2-methylpropan-1-one represented by formula (20) with lithium chloride to convert the methoxy group at the 5-position of the phenyl group into a hydroxyl group, thereby synthesizing the compound 1-(5-hydroxy-4-methoxy-2-nitrophenyl)-2-methylpropan-1-one represented by formula (21). Also, as the solvent, DMF (N,N-dimethylformamide) or the like may be used.

[0114] The above step (t) involves treating the compound represented by formula (21) with tert-butyl 2-bromoacetate represented by formula (22) in the presence of potassium carbonate to protect the hydroxyl group at the 5-position of the phenyl group, thereby synthesizing the compound tert-butyl 2-(5-isobutyryl-2-methoxy-4-nitrophenoxy)acetate represented by formula (23). Also, as the solvent, DMF (N,N-dimethylformamide) or the like may be used.

[0115] The above step (u) involves reducing the compound represented by formula (23) using sodium borohydride (NaBH4) to convert the isobutyryl group into a 1-hydroxy-2-methylpropyl group, thereby synthesizing the compound tert-butyl 2-(5-(1-hydroxy-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate represented by formula (24). Also, as the solvent, methanol or the like may be used.

[0116] In the step (v) above, the compound represented by formula (24) is treated with N,N'-disuccinimidyl carbonate represented by formula (25) and triethylamine to protect the 1-hydroxy-2-methylpropyl group, thereby synthesizing the compound tert-butyl 2-(5-(1-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate represented by formula (26). As the solvent, acetonitrile or the like may be used.

[0117] In the step (w) above, the compound represented by formula (26) is treated with di-tert-butyl(3-aminopropyl)phosphonate represented by formula (27) and triethylamine to form an amide bond, thereby synthesizing the compound tert-butyl 2-(5-(1-(((3-(di-tert-butoxyphosphoryl)propyl)carbamoyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate represented by formula (28). As the solvent, THF (tetrahydrofuran) or the like may be used.

[0118] In the step (x) above, the compound represented by formula (28) is treated with hydrochloric acid and dioxane to convert the tert-butyl group to a hydroxyl group and the tert-butoxycarbonyl group to a carboxyl group respectively, thereby synthesizing the compound 2-(2-methoxy-5-(2-methyl-1-(((3-phosphonopropyl)carbamoyl)oxy)propyl)-4-nitrophenoxy)acetic acid represented by formula (5-9). As the solvent, acetic acid or the like may be used.

[0119] [Specific Examples of the Method for Producing Compounds] A compound having a carboxyl group at the end of the functional group on the benzene ring can be synthesized, for example, by the following route. [Chemical formula] [Chemical formula]

[0120] A compound having an amino group at the end of a functional group on a benzene ring can be synthesized, for example, by the following route. [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula]

[0121] A compound having a thiol group at the end of a functional group on a benzene ring can be synthesized, for example, by the following route. [Chemical formula] [Chemical formula]

[0122] A compound having a hydroxy group at the end of a functional group on a benzene ring can be synthesized, for example, by the following route. [Chemical formula] [Chemical formula]

[0123] In addition, in each synthesis, each agent used to add a phosphate ester group to a compound can be synthesized, for example, by a reaction route represented by the following reaction formula. [Chemical formula]

[0124] The wavelength of the irradiation light necessary for cleaving sites X' and X'' of such a compound varies depending on the species of R1' to R4' and R1'' to R4''. For example, when the only group other than the carboxy group, amino group, hydroxy group or thiol group, and the group represented by any of formulas (II) to (IX) among R1' to R4' and R1'' to R4'' is a hydrogen atom, deprotection (for example, cleavage at site X') is effected with light having a wavelength of less than 200 nm to 300 nm, but deprotection does not occur with light having a wavelength of 300 nm to 400 nm. On the other hand, for example, when an ether bond (an alkoxy group such as a methoxy group or an ethoxy group) is present as the group other than the carboxy group, amino group, hydroxy group or thiol group, and the group represented by any of formulas (II) to (IX) among R1' to R4' and R1'' to R4'', deprotection is effected not only with light having a wavelength of less than 200 nm to 300 nm, but also with light having a wavelength of 300 nm to 400 nm. Thus, by utilizing the difference in the wavelength of the light necessary for deprotection due to the difference in the functional groups on the benzene ring, the presence or absence of deprotection can be controlled. In this way, if site X' is made not to be cleaved with light having a wavelength of 300 nm to 400 nm, while site X'' is made to be cleaved with light having a wavelength of 300 nm to 400 nm, both X' and X'' are deprotected with light having a wavelength of less than 200 nm to 300 nm, but only X'' is deprotected with light having a wavelength of 300 nm to 400 nm. If light irradiation with a wavelength of less than 200 nm to 300 nm and light irradiation with a wavelength of 300 nm to 400 nm are performed using masks with different patterns, there will be three types of modified forms on the substrate: a location where both X' and X'' are deprotected, a location where only X'' is deprotected, and a location where neither X' nor X'' is deprotected.

[0125] ≪Surface treatment agent≫ The surface treatment agent according to this embodiment contains the compound represented by the above-described formula (I). Since R6 in formula (I) is an alkylene group, a stable SAM can be formed.

[0126] The surface treatment agent according to this embodiment is not particularly limited in its use as long as it is used to treat and modify the surface of a substrate as an object to be treated. For example, as will be described later, it can be used to form a chemical bond by dehydration condensation between the phosphonic acid group in the compound represented by the above formula (I) and the hydroxy group on the surface of the substrate to modify the surface.

[0127] ≪Surface treatment method≫ The surface treatment method according to this embodiment includes at least a surface modification step of forming a chemical bond and modifying at least a part of the surface of a substrate using the compound represented by the above formula (I) with the phosphate group the compound has. Further, this surface modification method may have a light irradiation step after the surface modification step.

[0128] FIG. 1 is a schematic diagram for explaining the surface treatment method according to this embodiment. In FIG. 1, as an example of the compound represented by formula (I), the compound represented by the above formula (5-9) is used. Hereinafter, in this section, the compound represented by formula (5-9) is referred to as a "surface modification compound".

[0129] First, a surface modification compound is applied to the surface of the substrate 1, and dehydration condensation is carried out between the hydroxyl group of the substrate and the phosphate group of the surface modification compound to bond the two and form a surface modification compound layer 2 (S1). At this point, the carboxyl group that the surface modification compound has is exposed on the surface of the surface modification compound layer 2 of the substrate.

[0130] In this way, light is irradiated onto a part of the surface of the surface modification compound layer 2 using a photomask or the like (S2). As described above, in the light irradiation part 22, since the surface modification compound has a nitrobenzyl group, deprotection occurs and an amino group is exposed on the surface. On the other hand, in the non-light irradiation part 21, the carboxyl group that the surface modification compound has is exposed in the same manner as the surface modification compound layer 2. In this way, a plurality of different functional groups can be introduced onto one substrate with only one light irradiation.

[0131] Hereinafter, each step will be described in detail.

[0132] [Surface modification process] The surface modification process is a process of forming a chemical bond and modifying at least a part of the surface of a substrate using the phosphoric acid group of the compound represented by the above formula (I).

[0133] The surface of the substrate is modified by performing, for example, a dehydration condensation reaction or the like between the phosphonic acid group in the above formula (I). Specifically, examples of the group that undergoes a dehydration condensation reaction with the phosphonic acid group in the above formula (I) include a hydroxy group and the like.

[0134] The substrate is not particularly limited and may be, for example, an inorganic material or an organic material, but an inorganic material is preferred. The inorganic material is not particularly limited, and examples thereof include metals (by reaction with the oxide layer on the surface) and metal oxides, such as ITO (Indium Tin Oxide), silicon, silica gel, glass, alumina, titanium oxide, zirconium oxide, mica, and the like. Examples of the organic material include polyester, polycarbonate, polyimide, carbon nanotube, graphene, and the like.

[0135] The method for treating the surface of the object to be treated is not particularly limited. The compound represented by the above formula (I) may be directly applied to the surface of the object to be treated, or may be applied to the surface of the substrate in a state dissolved in a solvent (for example, ethanol, 2-propanol, tetrahydrofuran, etc.) in which the compound is soluble. Further, after the surface of the substrate is modified by directly applying the compound represented by the above formula (I) to the surface of the substrate, light irradiation may be performed on the surface to desorb a photodegradable group from the surface and introduce a functional group onto the surface. Furthermore, a group capable of reacting with the functional group may be reacted with the functional group introduced onto the surface to further modify the surface.

[0136] The shape of the substrate surface is not particularly limited and may be planar, spherical, or may include any part of these.

[0137] [Light irradiation step] The light irradiation step is a step of irradiating, with light having a wavelength of less than 200 to 300 nm or 200 nm or more and 400 nm or less for a compound having absorption at 300 to 400 nm, a part of the substrate where the portion modified with the compound represented by the formula (I) is located, after the surface modification step described above.

[0138] The method of irradiating light is not particularly limited, and examples thereof include a method of performing pattern exposure using a photomask or the like.

[0139] [Other steps] The surface treatment method of the present embodiment may or may not include conventional known steps other than the above surface treatment steps.

[0140] For example, before the above surface treatment step, there may be a step of performing pretreatment such as cleaning (cleaning with a liquid, ultrasonic cleaning, etc.), drying, and UV irradiation on the object to be treated.

[0141] [When introducing three or more kinds of functional groups] Above, mainly, the method for introducing two kinds of functional groups into the substrate has been described. However, by using the compound of the present embodiment, three or more kinds of functional groups can be introduced into the substrate more simply than the conventional method. For example, prepare two kinds of compounds in which both the functional group at the end of the functional group on the benzene ring and the functional group formed when deprotected (the site X is cleaved) are different, apply or print each on the substrate, and appropriately irradiate with light for patterning. Thereby, it is possible to introduce a total of four kinds of functional groups on the substrate by two applications or printings. That is, by combining the compounds of the present embodiment, the number of applications or printings can be reduced to 1 / 2.

[0142] ≪Modification examples of the compound≫ The compound of the present embodiment is represented by the following formula (Ia). [Chemical formula] (At least one of R1’ to R4’ and R1’’ to R4’’ is each independently a carboxy group, an amino group, a hydroxy group or a thiol group, or a group represented by any of the following formulas (II) to (IX), and the rest are each independently a hydrogen atom, an alkyl group, a perfluoroalkyl group or an alkoxy group which may have a perfluoroalkyl group as a substituent. R5’ and R5’’ are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom as a substituent. X’ and X’’ are each independently a group represented by any of the following formulas (X) to (XVI). R6’ has at least an alkylene group having 1 to 50 carbon atoms which may have a branched chain and a cyclic structure at the X’-side end and the P-side end, and further has an alkylene group having 1 to 50 carbon atoms, a perfluoroalkylene group having 1 to 50 carbon atoms which may have a branched chain and a cyclic structure, an aromatic ring, an ether group, a carbonyl group, and an aromatic ring which may be substituted with one or more of them, and may include a combination of two or more of these groups, and further they may be groups which may be substituted with a carboxy group, an amino group, a hydroxy group or a thiol group.)

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chem.

Chem.

Chem.

Chem.

[0143] R1’ to R4’ and R1’’ to R4’’ can use the same ones as the above R1 to R4, R5’ and R5’’ can use the same ones as the above R5, and X’ and X’’ can use the same ones as the above X.

[0144] R6’ has at least an alkylene group with 1 to 50 carbon atoms which may have a branched chain and a cyclic structure at the X’ side end and the P side end, and further has an alkylene group with 1 to 50 carbon atoms, a perfluoroalkylene group with 1 to 50 carbon atoms which may have a branched chain and a cyclic structure, an aromatic ring, an ether group, a carbonyl group, and an aromatic ring which may be substituted with one or more of them, and may include a combination of two or more of these groups. Furthermore, it is a group which may be substituted with a carboxy group, an amino group, a hydroxy group or a thiol group. Note that R6’ has an alkylene group with 1 to 25 carbon atoms, and may contain a plurality (of parts) of a perfluoroalkylene group with 1 to 25 carbon atoms which may have a branched chain and a cyclic structure, an aromatic ring, an ether group or a carbonyl group respectively.

[0145] The compounds as described above can be synthesized by the synthetic route shown below.

Chem.

Examples

[0146] Hereinafter, the present invention will be described in more detail by showing examples, but the present invention is not limited to the following examples at all.

[0147] (Example 1) (Synthesis of the compound used as the surface treatment agent) The compound represented by the formula (5-9) was synthesized according to the formula shown below. Each reaction will be described below. [Chemical formula]

[0148] [Step(s)] Synthesis of 1-(5-hydroxy-4-methoxy-2-nitrophenyl)-2-methylpropan-1-one [Chemical formula]

[0149] 1-(4,5-Dimethoxy-2-nitrophenyl)-2-methylpropan-1-one (5.00 g, 19.7 mmol, 1.0 eq.), lithium chloride (17.2 g, 0.406 mol, 21 eq.), and DMF (30 mL) were added to a two-necked eggplant flask at room temperature. After stirring at 165 °C for 2 hours, DMF was removed by distillation under reduced pressure. AcOEt (200 mL) and an acidic aqueous solution (80 mL of pure water + 20 mL of 2N HCl) were added to the residue, and the insoluble solid was removed by suction filtration. After transferring the filtrate to a separatory funnel, the aqueous layer was removed. The organic layer was washed with an acidic aqueous solution (90 mL of pure water + 20 mL of 2N HCl), pure water (100 mL), and sat. NaCl aq. (100 mL), dried (MgSO4), filtered, and concentrated. The obtained crude product was purified by silica gel column chromatography (AcOEt / hexane = 1 / 1) to obtain a yellow solid (1.16 g, 4.85 mmol, 25%). 11H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.68 (s, 1H), 6.81 (s, 1H), 6.25 (br, 1H), 4.03 (s, 3H), 2.90 (sept., J = 7.0 Hz, 1H), 1.22 (d, J = 6.8 Hz, 6H). 13 13C NMR (100 MHz, CDCl3, TMS): δ (ppm) 206.9, 151.1, 146.6, 138.1, 133.3, 113.3, 106.9, 56.71, 41.39, 18.59. HR-MS (ESI) m / z: Calcd for C 11 H 13 N1Na1O5 [M + Na] + = 262.0691; Found 262.0692. FT-IR (KBr): 3335 cm -1 (OH), 1692 cm -1 (C=O), 1518 cm -1 , 1330 cm -1 (NO2).

[0150] [Engineering (t)] Synthesis of tert-butyl 2-(5-isobutyryl-2-methoxy-4-nitrophenoxy)acetate

Chemical Structure

[0151] Into a nitrogen-substituted two-necked eggplant flask, 1-(5-hydroxy-4-methoxy-2-nitrophenyl)-2-methylpropan-1-one (1.00 g, 4.18 mmol, 1.0 eq.), potassium carbonate (1.73 g, 12.5 mmol, 3.0 eq.), and DMF (15 mL) were added, and the mixture was stirred at room temperature for 3 hours. tert-Butyl 2-bromoacetate (1.22 g, 6.25 mmol, 1.5 eq.) was added, and the mixture was stirred at 70 °C for 3 hours, then returned to room temperature and EtOAc (100 mL) was added. The organic layer was washed with pure water (2 × 50 mL) and sat. NaClaq. (3 × 50 mL), dried (MgSO4), filtered, and concentrated. The obtained crude product was purified by silica gel column chromatography (AcOEt / hexane = 1 / 4) to obtain a yellow solid (1.45 g, 4.10 mmol, 98%). 1 1H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.68 (s, 1H), 6.56 (s, 1H), 4.69 (s, 2H), 4.00 (s, 3H), 2.89 (sept., J = 6.9 Hz, 1H), 1.47 (s, 9H), 1.19 (d, J = 6.8 Hz, 6H). 13 13C NMR (100 MHz, CDCl3, TMS): δ (ppm) 206.9, 166.3, 152.0, 149.7, 139.2, 131.8, 111.1, 107.4, 83.38, 66.10, 56.63, 41.47, 27.99, 18.71. HR-MS (ESI) m / z: Calcd for C 17 H 23 14N1Na1O7 [M+Na] + = 376.1372; Found 376.1355. FT-IR (KBr): 1746 cm -1 , 1695 cm -1 (C=O), 1537 cm -1 (NO2), 1335 cm -1 (NO2).

[0152] [Step (u)] Synthesis of tert-butyl 2-(5-(1-hydroxy-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate [Chemical]

[0153] tert-butyl 2-(5-isobutyryl-2-methoxy-4-nitrophenoxy)acetate (504 mg, 1.43 mmol, 1.0 eq.) and MeOH (8 mL) were added to a one-neck eggplant flask and dissolved. Then, NaBH4 (70.1 mg, 1.85 mmol, 1.3 eq.) was added at room temperature. After stirring for 2 hours, it was diluted with EtOAc (100 mL), and the organic layer was washed with acidic aqueous solution (50 mL of pure water + 2 mL of 2N HCl), pure water (50 mL), 5% NaHCO3 (50 mL), and sat. NaCl aq. (50 mL), dried (MgSO4), filtered, and concentrated. The obtained crude product was purified by silica gel column chromatography (AcOEt / hexane = 1 / 3) to obtain a yellow viscous solid (459 mg, 1.29 mmol, 90%). 1 H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.58 (s, 1H), 7.09 (s, 1H), 5.25 (t, J = 6.8 Hz, 1H), 4.70 (s, 2H), 3.95 (s, 3H), 2.19 (br, 1H), 2.03 - 1.92 (m, 1H), 1.49 (s, 9H), 0.954 and 0.904 (d, J = 7.0 Hz, 6H). 13 C NMR (100 MHz, CDCl3, TMS): δ (ppm) 166.7, 151.3, 147.8, 140.9, 134.3, 111.3, 108.3, 83.02, 73.45, 65.81, 56.39, 34.29, 28.02, 19.90, 16.49. HR-MS (ESI) m / z: Calcd for C 17 H 25 N1Na1O7 [M + Na] + = 378.1529; Found 378.1516. FT-IR (KBr): 3539 cm -1 (OH), 1752 cm -1 (C=O), 1519 cm -1 (NO2), 1334 cm -1 (NO2).

[0154] [Engineering (v)] Synthesis of tert-butyl 2-(5-(1-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate

Chem.

[0155] To a nitrogen-substituted two-necked test tube, tert-butyl 2-(5-(1-hydroxy-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate (419 mg, 1.18 mmol, 1.0 eq.), N,N’-disuccinimidyl carbonate (610 mg, 2.4 mmol, 2.02 eq.), CH3CN (5 mL), and Et3N (480 μL, 3.46 mmol, 2.9 eq.) were added, and the mixture was stirred at room temperature for 24 hours. The reaction solution was diluted with EtOAc (150 mL), and the organic layer was washed with acidic aqueous solution (50 mL of pure water + 2 mL of 2N HCl), pure water (50 mL), and sat. NaClaq. (50 mL), dried (MgSO4), filtered, and concentrated. The obtained crude product was purified by silica gel column chromatography (AcOEt / hexane = 3 / 7) to obtain a yellow solid (459 mg, 0.925 mmol, 78%). 1 H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.68 (s, 1H), 6.85 (s, 1H), 6.38 (d, J = 4.8 Hz, 1H), 4.80 (s, 2H), 3.96 (s, 3H), 2.80 (s, 1H), 2.30 - 1.92 (m, 1H), 1.49 (s, 9H), 1.09 and 1.00 (d, J = 7.0 Hz, 6H). 13 C NMR (100 MHz, CDCl3, TMS): δ (ppm) 168.5, 166.8, 151.9, 151.6, 148.7, 128.3, 110.1, 108.7, 83.19, 82.98, 66.03, 56.44, 33.53, 28.02, 25.41, 19.35, 16.41. HR-MS (ESI) m / z: Calcd for C22 H 28 N2Na1O 11 [M+Na] + =519.1591; Found 519.1593. FT-IR(KBr): 1814 cm -1 , 1790 cm -1 , 1744 cm -1 (C=O), 1524 cm -1 , 1338 cm -1 (NO2).

[0156] Synthesis of tert-butyl 2-(5-(1-(((3-(di-tert-butoxyphosphoryl)propyl)carbamoyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate

Chem.

[0157] Into a nitrogen-substituted two-necked test tube, tert-butyl 2-(5-(1-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate (120 mg, 0.242 mmol, 1.0 eq.), di-tert-butyl (3-aminopropyl) phosphonate (72.2 mg, 0.287 mmol, 1.2 eq.), THF (1.0 mL), and Et3N (50.0 μL, 0.361 mmol, 1.5 eq.) were added, and the mixture was stirred at room temperature for 24 hours. The resulting reaction solution was concentrated, and the crude product was purified by silica gel column chromatography (MeOH / CH2Cl2 = 5 / 95) to obtain a yellow viscous solid (148 mg, 0.234 mmol, 97%). 11H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.60 (s, 1H), 6.84 (s, 1H), 6.19 (d, J = 5.6 Hz, 1H), 5.25 (t, J = 6.0 Hz, 1H), 4.66 (s, 2H), 3.94 (s, 3H), 3.32 - 3.07 (m, 2H), 2.15 - 2.04 (m, 1H), 1.82 - 1.70 (m, 2H), 1.68 - 1.56 (2H (predicted) overlapped with water’s peak), 1.49 (s, 9H), 1.48 and 1.47 (s, 18H), 0.97 and 0.95 (d, J = 6.8 Hz, 6H). 13 13C NMR (100 MHz, CDCl3, TMS): δ (ppm) 166.8, 155.7, 151.1, 148.1, 141.6, 131.4, 111.2, 108.4, 82.93, 81.85 (d, J = 8.6 Hz), 81.81 (d, J = 8.6 Hz), 75.38, 66.22, 56.38, 41.15 (d, J = 14.8 Hz), 33.43, 30.44 (d, J = 3.6 Hz), 30.42 (d, J = 3.6 Hz), 28.02, 27.47 (d, J = 145 Hz), 23.69 (d, J = 5.8 Hz), 19.31, 17.29. 31 31P{ 1 1H} NMR (160 MHz, CDCl3, H3PO4) δ (ppm) 23.6. ESI-MS m / z: Calcd for C 29 25 50 H 11 4 + N2Na1O -1 3 -1 P [M + Na] -1 = 655.2972; Found 655.2951. FT-IR (KBr): 1750 cm -1 -1

[0158] [Engineering (x)] Synthesis of 2-(2-methoxy-5-(2-methyl-1-(((3-phosphonopropyl)carbamoyl)oxy)propyl)-4-nitrophenoxy)acetic acid [Chem.]

[0159] tert-butyl 2-(5-(1-(((3-(di-tert-butoxyphosphoryl)propyl)carbamoyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate (64.0 mg, 0.101 mmol) and AcOH (6 mL) were added to a one-neck eggplant flask and dissolved. Then, 4N HCl / dioxane (1.5 mL) was slowly added dropwise. After stirring overnight at room temperature, the reaction solution was diluted with pure water (50 mL). The aqueous layer was washed with chloroform (3 × 50 mL), and then the aqueous layer in which the target product was dissolved was extracted with AcOEt (3 × 50 mL). The collected organic layer was dried, filtered, concentrated, and dried under vacuum to obtain a yellow solid (40.0 mg, 86.1 μmol, 85%). 1 H NMR (400 MHz, CD3OD): δ (ppm) 7.68 (s, 1H), 6.99 (s, 1H), 6.12 (d, J = 5.2 Hz, 1H), 4.81 (d, J = 3.6 Hz, 2H), 3.93 (s, 3H), 3.17 - 3.05 (m, 2), 2.16 - 2.08 (m, 1H), 1.78 - 1.61 (m, 4H), 1.49 (s, 9H), 0.99 and 0.97 (d, J = 6.8 Hz, 6H). 13 C NMR (100 MHz, CD3OD): δ (ppm) 171.8, 158.4, 153.0, 149.8, 142.6, 132.5, 112.5, 109.7, 76.5, 66.6, 56.9, 42.2 (d, J = 19.1 Hz), 34.6, 25.6 (d, J = 138 Hz), 24.6 (d, J = 3.8 Hz), 19.8, 17.3. 31 P{ 1 H}NMR (160 MHz, CD3OD, H3PO4, 308K) δ (ppm) 30.6. HR-MS (ESI) m / z: Calcd for C 17 H 25 N2Na1O 11 P [M+Na] + = 487.7094; Found 487.7055. FT-IR (KBr): 1522 cm -1, 1334 cm -1 (NO2), 1279 (P=O).

[0160] <Deprotection reaction in the solution of the compound> 3 mL of a 0.1 mM ethanol solution of the compound represented by the formula (5-9) was placed in a quartz cell with Teflon (registered trademark), and irradiated with light having a wavelength of 365 nm and an illuminance of 25 mW / cm 2 for 60 seconds using an ultra-high pressure mercury lamp. Every 10 seconds of irradiation time, a UV-vis spectrum in the range of wavelengths from 240 nm to 450 nm was measured using a V-730 manufactured by JASCO Corporation. Figure 2 is the UV-vis spectrum after light irradiation of the ethanol solution of the compound represented by the formula (5-9).

[0161] The photodegradation reaction of the compound represented by the formula (5-9) is represented by the following formula. According to Figure 2, it was found that the peaks of the carbonyl group and the nitroso group derived from the compound represented by the formula (30) generated by photodegradation increased with time.

[0162] Electrospray ionization mass spectrometry (ESI-MS) of the compound represented by the formula (5-9) was performed. Figure 3(a) is the mass spectrum before irradiating the compound represented by the formula (5-9) with light, and (b) is the mass spectrum after irradiating the compound represented by the formula (5-9) with light for 30 seconds. In the mass spectrum after irradiating with light for 30 seconds, a peak of m / z = 281 derived from the compound represented by the formula (30) was confirmed.

[0163] <Surface treatment of indium-doped tin oxide (ITO) substrate> After subjecting the ITO substrate to ultrasonic cleaning, UV / O3 treatment was performed on its surface to hydrophilize the surface. Subsequently, it was immersed in a 0.1 mM ethanol solution of the compound represented by the formula (5-9) for 24 hours and annealed at 100 °C for 3 hours to obtain a surface-modified ITO substrate sample modified with the compound represented by the formula (5-9).

[0164] <Deprotection reaction by light irradiation of the ITO substrate sample> The surface-modified ITO substrate sample obtained as described above was immersed in acetone, and irradiated with light having a wavelength of 365 nm and an illuminance of 25 mW / cm 2 for 180 seconds using an ultra-high pressure mercury lamp. Table 1 shows the water contact angle and the intensity of the XPS spectrum of the surface-modified ITO substrate sample before and after light irradiation. It was found that the peak (N(1s), 407 eV) derived from the nitro group among the deprotected groups disappeared. On the other hand, the peak of phosphorus (P(2p), 134 eV) derived from the phosphate group for bonding to the ITO substrate was confirmed to remain.

[0165] <Formation of Pattern with Fluorescent Particles> The surface-modified ITO substrate sample obtained as described above was irradiated with light having an illuminance of 25 mW·cm -2 and a wavelength of 365 nm for 180 seconds through a photomask (line width: 20 μm, L / S = 1:1). Fig. 4 is an optical microscope image of the photomask used in this example. After irradiation, ultrasonic cleaning was performed with acetone for 2 minutes and dried with a nitrogen stream. The patterning of the carboxy group was obtained by immersing in an aqueous solution of 30 μm / 10 mL of an amine-modified fluorescent particle solution (particle size: 0.2 μm, Ex / Em: 505 / 515, manufactured by Thermo Fisher Scientific) for 5 minutes and then rinsing with pure water. The patterning of the amino group was obtained by immersing the substrate in a 0.1 M hydrochloric acid aqueous solution for 10 seconds, then drop-casting a carboxylate-modified fluorescent particle solution (particle size: 0.5 μm, Ex / Em: 580 / 605, manufactured by Thermo Fisher Scientific), rinsing with pure water, and drying with a nitrogen stream. The fluorescent particle pattern was observed with a fluorescence microscope (IX70, manufactured by Olympus).

[0166] Fig. 5 is a fluorescence microscope image of the surface-modified ITO substrate sample after binding amine-modified fluorescent particles. In Fig. 5, it was confirmed that the lightly contrasted portions emit green light.

[0167] Fig. 6 is a fluorescence microscope image of the surface-modified ITO substrate sample after binding carboxylate-modified fluorescent particles. In Fig. 6, it was confirmed that the lightly contrasted portions emit red light.

[0168] Furthermore, silver nanoparticle ink was dropped onto the surface-modified ITO substrate sample that had been subjected to light irradiation in the same manner. The silver nanoparticles adhere to the amino groups on the surface of the portion irradiated with light. FIG. 7 is an optical microscope image of the surface-modified ITO substrate sample after binding the silver nanoparticles. In FIG. 7, it was confirmed that silver adhered to the lightly contrasted portions.

[0169] Also, the same operation was performed with a different photomask for patterning. FIG. 8 is an optical microscope image of the surface-modified ITO substrate sample after binding silver nanoparticles to the patterned areas. It was confirmed that fine patterning is also possible by using the compound of this embodiment as a surface treatment agent.

[0170] (Example 2) Except that the following steps (w) and (x) were performed instead of steps (w) and (x) of Example 1 to synthesize the compound represented by formula (42), the same procedure as in Example 1 was carried out.

[0171] [Step (w)] Synthesis of tert-butyl 2-(5-(1-(((3-(di-tert-butoxyphosphoryl)propoxy)carbonyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate [Chemical formula]

[0172] In a nitrogen-substituted two-necked test tube, tert-butyl 2-(5-(1-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)-2-methylpropyl)-2-methoxy‐4‐nitrophenoxy)acetate (400 mg, 0.807 mmol, 1.0 eq.), di-tert-butyl(3-hydroxypropyl)phosphonate (300 mg, 1.21 mmol, 1.5 eq.), THF (8.0 mL), and dimethylaminopyridine (200 mg, 1.65 mmol, 2.1 eq.) were added. After stirring at 70 °C for 72 hours, the mixture was returned to room temperature and EtOAc (100 mL) was added. The organic layer was washed with sat. NaHCO3 aq. (2 × 50 mL) and sat. NaCl aq. (3 × 50 mL), dried (MgSO4), filtered, and concentrated. The crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 1 / 1) to obtain a yellow viscous solid (291 mg, 0.460 mmol, 57%). 1 H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.60 (s, 1H), 6.85 (s, 1H), 6.18 (d, J = 6.2 Hz, 1H), 4.68 (s, 2H), 4.19 - 4.01 (m, 2H), 3.95 (s, 3H), 2.20 - 2.12 (m, 1H), 1.95 - 1.85 (m, 2H), 1.70 - 1.62 (m, 2H), 1.49 (s, 18H), 1.48 (s, 9H), 1.01 and 0.97 (d, J = 6.7 Hz, 6H). 31 P{ 1 H}NMR (160 MHz, CDCl3, H3PO4) δ (ppm) 22.4.

[0173] [Step (x)] Synthesis of 2-(2-methoxy-5-(2-methyl-1-(((3-phosphonopropoxy)carbonyl)oxy)propyl)-4-nitrophenoxy)acetic acid

Chemical Structure

[0174] tert-Butyl 2-(5-(1-(((3-(di-tert-butoxyphosphoryl)propoxy)carbonyl)oxy)-2-methylpropyl)-2-methoxy-4-nitrophenoxy)acetate (193 mg, 0.305 mmol) and MeOH (3 mL) were added to a one-necked eggplant flask and dissolved. Then, 4N HCl / dioxane (1.5 mL) was slowly added dropwise. After stirring at room temperature for 48 hours, the reaction solution was diluted with pure water (50 mL), and then sat. NaHCO3 aq. was added to make the solution basic. The aqueous layer was washed with chloroform (3 × 50 mL). 2N HCl aq. was added to the aqueous layer in which the target product was dissolved to make the solution acidic, and then it was extracted with AcOEt (3 × 50 mL). The collected organic layer was dried, filtered, concentrated, and dried under vacuum to obtain a yellow solid (95.1 mg, 0.210 mmol, 69%). 1 1H NMR (400 MHz, CDCl3): δ (ppm) 7.61 (s, 1H), 6.86 (s, 1H), 6.14 (d, J = 5.9 Hz, 1H), 4.79 (s, 2H), 4.15 - 4.01 (m, 2H), 3.95 (s, 3H), 2.20 - 2.12 (m, 1H), 1.98 - 1.88 (m, 2H), 1.83 - 1.74 (m, 2H), 1.00 and 0.99 (d, J = 6.7 Hz, 6H). 31 P{ 1 1H} NMR (160 MHz, CDCl3, H3PO4) δ (ppm) 35.4.

[0175] (Example 3) (Synthesis of the compound used as the surface treatment agent) The compound represented by formula (55) was synthesized according to the formula shown below. Each reaction will be described below. [Chemical formula]

[0176] Synthesis of tert-butyl(3-(5-(1-hydroxy-2-methylpropyl)-2-methoxy-4-nitrophenoxy)propyl)carbamate

Chem.

[0177] Under a nitrogen atmosphere, 5-(1-hydroxy-2-methylpropyl)-2-methoxy-4-nitrophenol (1.00 g, 4.16 mmol, 1.0 eq.), K2CO3 (1.23 g, 8.90 mmol, 2.1 eq.) and CH3CN (6.0 mL) were added to a two-necked eggplant flask and stirred for 1 hour. Then, tert-Butyl(3-bromopropyl)carbamate (1.48 g, 6.27 mmol, 1.5 eq.) was added, and the mixture was refluxed at 80 °C, concentrated, diluted with AcOEt (100 mL), washed with water (100 mL × 3) and sat. NaCl aq. (100 mL × 2), dried (MgSO4), filtered, and concentrated. The obtained crude product was purified by silica gel column chromatography (AcOEt / hexane = 1 / 1) to obtain a yellow viscous solid (1.35 g, 3.38 mmol, 81%). 1 1H NMR (600 MHz, CDCl3, TMS): δ (ppm) 7.55 (s, 1H), 7.19 (s, 1H), 5.33 (br, 1H), 5.26 (d, J = 5.3 Hz, 1H), 4.24 - 4.17 (m, 2H), 3.94 (s, 3H), 3.38 (q, J = 4.7 Hz, 2H), 2.24 (br, 1H), 1.46 (s, 9H), 0.95 and 0.94 (d, J = 6.5 Hz, 6H).

[0178] Synthesis of 1-(5-(3-((tert-butoxycarbonyl)amino)propoxy)-4-methoxy-2-nitrophenyl)-2-methylpropyl-3-(diethoxyphosphoryl)propanoate

Chem.

[0179] Under a nitrogen atmosphere in a Schlenk tube, tert-butyl(3―(5-(1-hydroxy-2-methylpropyl)-2-methoxy-4-nitrophenoxy)propyl)carbamate (1.06 g, 2.66 mmol, 1.0 eq), phosphonic acid (1.32 g, 6.28 mmol, 2.4 eq), EDC·HCl (610 mg, 3.19 mmol, 1.2 eq), DMAP (651 mg, 5.32 mmol, 2.0 eq) and 20 mL of dry THF were added under an ice bath and stirred for 30 minutes. Then the ice bath was removed, and after stirring at room temperature for 24 hours, phosphonic acid (660 mg, 3.14 mmol, 1.2 eq) and 0.611 g (3.19 mmol, 1.2 eq) of EDC·HCl were added, and the mixture was stirred at room temperature for 24 hours. Then, it was concentrated, diluted with 150 mL of AcOEt, washed with sat. NaHCO3 (20 mL × 3), water (100 mL × 3) and set. NaCl aq. (100 mL × 2), dried (MgSO4), filtered, concentrated, and purified by silica column chromatography (hexane / AcOEt = 1 / 2 → AcOEt) to obtain a yellow viscous solid (451 mg, 0.764 mmol). 1 1H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.57 (s, 1H), 6.87 (s, 1H), 6.32 (d, J = 3.2 Hz, 1H), 5.54 (br, 1H), 4.02 - 4.18 (m, 6H), 3.93 (s, 3H), 3.35 - 3.39 (m, 2H), 2.56 - 2.68 (m, 2H), 2.17 - 2.19 (m, 1H), 1.98 - 2.12 (m, 4H), 1.45 (s, 8H), 1.24 - 1.34 (m, 8H), 1.00 (d, J = 6.8 Hz, 3H) and 0.97 (d, J = 7.2 Hz, 3H) 31 P{ 1 1H} NMR (160 MHz, CDCl3, H3PO4) δ (ppm) 30.1.

[0180] Synthesis of [Chem.]

[0181] In a eggplant flask, 1-(5-(3-((tert-butoxycarbonyl)amino)propoxy)-4-methoxy-2-nitrophenyl)-2-methylpropyl-3-(diethoxyphosphoryl)propanoate (40 mg, 0.0677 mmol, 1.0 eq.), 3 mL of CH3CN and 34 μL of Me3SiBr (405 mg, 0.265 mmol, 3.0 eq.) were added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 26 hours. Then, 5 mL of MeOH was added and the mixture was stirred for 3 hours to obtain a yellow viscous substance (40 mg, 92 mmol). 1 1H NMR (400 MHz, CDCl3, TMS): δ (ppm) 7.57 (s, 1H), 7.00 (s, 1H), 6.25 (m, 1H), 4.13 - 4.38 (m, 2H), 3.93 (s, 1H), 2.48 - 2.96 (m, 2H), 2.35 (m, 3H), 2.17 - 2.22 (m, 4H), 1.19 - 1.44 (m, 6H), 0.97 - 1.04 (m, 4H). 31 31P{ 1 1H} NMR (160 MHz, CDCl3, H3PO4) δ (ppm) 37.7.

[0182] Note that by forming a semiconductor layer on the carboxyl group side of such a surface-modified ITO substrate sample and using silver nanoparticles as electrodes, it is considered that a fine semiconductor device can be formed.

[0183] As described above, it was found that by using the compound of the present embodiment as a surface treatment agent, two kinds of functional groups with different properties can be introduced onto the substrate.

Explanation of Symbols

[0184] 1 Substrate 2 Surface modification compound layer 21 Non-light-irradiated part 22 Light-irradiated part

Claims

1. A compound represented by the following formula (I). 【Chemical 1】 (R １ ~R ４ at least one of which is independently a carboxy group, an amino group, a hydroxy group or a thiol group, or a group represented by any one of the following formulas (II) to (IX), and the rest are each independently a hydrogen atom, an alkyl group, a perfluoroalkyl group or an alkoxy group which may have a perfluoroalkyl group as a substituent, R ５ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom as a substituent, X is a group represented by any one of the following formulas (X), (XII), and (XVI), R ６ is an alkylene group when X is a group represented by any of the following formulas (X) and (XII), and is a single bond or an alkylene group when X is a group represented by the following formula (XVI).) 【Chemical 2】 (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, and n is an integer of 1 to 25.) 【Chemical Formula 3】 (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, and n is an integer of 1 to 25.) 【Chemical 4】 (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, and n is an integer of 1 to 25.) [Chemical Formula 5] (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, and n is an integer of 1 to 25.) 【Chemical Formula 6】 (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, and n is an integer of 1 to 25.) 【Chemical Formula 7】 (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, and n is an integer of 1 to 25.) 【Chemical Formula 8】 (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, W is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 25 carbon atoms, and n is an integer of 1 to 25.) 【Chemical Formula 9】 (Y is a hydrogen atom or a halogen atom, Z is a carboxy group, an amino group, a hydroxy group, or a thiol group, W is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 25 carbon atoms, and n is an integer of 1 to 25.) 【Chemical 10】 【Chemical 11】 【Chemical Formula 12】

2. The aforementioned R ５ The compound according to claim 1, wherein R is an isopropyl group.

3. The functional group generated by light irradiation is R １ ~R ４ The compound according to claim 1 or 2, which is not the same as the carboxy group, amino group, hydroxy group or thiol group present in

4. A surface treatment agent containing the compound according to any one of Claims 1 to 3.

5. A surface treatment method having at least a surface modification step of forming a chemical bond and modifying at least a part of the surface of a substrate using the phosphate group of the compound according to any one of Claims 1 to 3.

6. The surface treatment method according to Claim 5, further having a light irradiation step of irradiating a part of the portion of the substrate modified with the compound with light having a wavelength of 200 nm or more and 400 nm or less after the surface modification step.

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