Light or heat-responsive cleavage molecular layer

Abstract

To provide: a cleavage molecular layer in which adhesion and peeling can be controlled through stimuli other than heat by using a change in bonding in a molecular layer; and a compound which constitutes the same.SOLUTION: Provided is a compound in which reversible cleavage and bonding are possible with light or heat. In one embodiment, the compound has a dimerized structure derived from an anthracene structure.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a photo- or thermo-responsive cleavage molecular layer and a compound for forming the same. In particular, the present invention relates to a surface treatment technique for a substrate using a photo- or thermo-responsive cleavage molecular layer.

Background Art

[0002] Methods for adhering substrates to each other or materials to each other using a substrate surface treatment technique have been reported so far. Patent Documents 1 and 2 disclose a surface modifier for a material using a novel compound and a bonding method using the same. Patent Documents 1 and 2 disclose a method of adsorbing a compound having a triazine ring on the material surface as a surface modifier to make the surfaces of different materials the same state and facilitate the processing of the materials. Examples of substrates to which the surface modifiers described in Patent Documents 1 and 2 can be applied include metals, ceramics, organic polymers, inorganic polymers, etc., and can be applied to various materials. It is also described that this surface modifier has the effect of improving the strength of adhesion between different materials. On the other hand, in the bonding method using the surface modifiers described in Patent Documents 1 and 2, the disassemblability between the bonded materials is not mentioned.

[0003] Further, Patent Document 3 describes a technique for bonding a resin member and a metal member, and provides a resin-metal composite material for the purpose of weight reduction of automobiles and aircraft, utilizing the property that an ester bond is cleaved by heating and recombines when returned to room temperature. In the resin-metal composite described in Patent Document 3, the ester bond portion contained in the resin is cleaved by heating, and a chemical bond is formed with the hydroxyl group on the metal surface, so that the resin and the metal are firmly adhered. Furthermore, it is described that when a blade is inserted into the bonding interface and peeled immediately after heating the composite material, it can be easily peeled off because the ester bond is cleaved. Patent Document 3 proposes an adhesion method that not only provides strong adhesion of the resin-metal composite but also imparts disassemblability in view of recycling.

[0004] On the one hand, for example, Patent Document 4 discloses a method for controlling the lyophilicity / lyophobicity of a substrate surface using two types of compounds: a compound having a group capable of undergoing a photo-dimerization reaction (e.g., anthracene) and a lyophilic group (e.g., silyl group), and a compound having a group capable of undergoing a photo-dimerization reaction (e.g., anthracene) and a lyophobic group (a fluorine-containing group). After depositing the compounds described in Patent Document 4 on the substrate surface, light irradiation through a photomask can limit the portions where the photo-dimerization reaction proceeds, enabling the patterning of lyophilicity / lyophobicity. Note that Patent Document 4 only discloses a method for controlling the properties of the substrate surface, and does not describe the use of the compound for adhesion between substrates or the disassembly using the cleavage reaction of the dimerized product.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Summary of the Invention

Problems to be Solved by the Invention

[0006] In the adhesion methods described in Patent Documents 1 and 2, 1) there is no report on the disassembly mechanism utilizing the bonding and dissociation in a specific structure in the molecular layer. On the other hand, in the adhesion methods referring to 2) disassembly properties as in Patent Document 3, there are operational restrictions such as peeling immediately after heating. Also, 3) the operation of disassembly by heating is difficult to apply to substrates where it is difficult to apply heat, and there is a problem that the substrate selection is limited. In view of the above problems, an object of the present invention is to provide a cleavage molecular layer capable of controlling adhesion and peeling by stimuli other than heat, and a compound constituting the same.

Means for Solving the Problems

[0007] In order to solve the above problems, the present inventors focused on the dimerization and cleavage mechanism of anthracene capable of cleavage and dimerization by applying stimuli such as heat and light, and conceived using the mechanism as a molecular layer for adhesion between materials. As a result of intensive studies, the present inventors have reached the solution of the above problems by utilizing the dimerization reaction and cleavage reaction in the molecular layer by light or heat stimuli. The present invention is an invention completed based on the above findings and includes the following aspects: One aspect of the present invention is 〔1〕A photo- or heat-responsive cleavage substrate having a first substrate and a cleavage molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, wherein the cleavage molecular layer is formed of a compound represented by any of the following formulas (I) to (VII), and relates to a photo- or heat-responsive cleavage substrate.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0008] Here, one embodiment of the photo- or thermoresponsive cleavage base material of the present invention is 〔2〕The photo- or thermoresponsive cleavage base material according to the above 〔1〕, characterized in that the compound is not a compound represented by the following formula (VIII).

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0009] Also, another aspect of the present invention is 〔8〕A method for cleaving the cleavage molecular layer in the photo- or thermo-responsive cleavage substrate according to the above 〔1〕 to 〔7〕, which includes a step of applying light or heat to the cleavage molecular layer. Also, another aspect of the present invention is 〔9〕A method for bonding the cleavage molecular layer cleaved by the method according to the above 〔8〕, which includes a step of applying light to the cleaved cleavage molecular layer.

Advantages of the Invention

[0010] According to the compound of the present invention, a cleavage molecular layer composed of the compound can be formed on a substrate. The cleavage molecular layer enables repeated control of adhesion and peeling by utilizing bond changes in the cleavage molecular layer. In addition, the cleavage molecular layer can maintain a state where it is easily peeled even after a lapse of time after stimulation by using a cleavage reaction caused by stimulation application, and can solve operational constraints. Furthermore, the cleavage molecular layer can utilize a photodissociation mechanism in addition to stimulation by heat. Also, the compound of the present invention can select a functional group according to the substrate for the purpose of forming a molecular layer, and can ensure diversity in substrate selection.

Brief Description of Drawings

[0011]

Figure 1

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[0012] One aspect of the present invention provides a photo- or thermoresponsive cleaved substrate having a first substrate and a cleaved molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, wherein the cleaved molecular layer is formed from a specific compound. Compounds having a structure similar to the specific compound forming the cleaved molecular layer and methods for producing the same are disclosed, for example, in Patent Document 4 and International Publication No. 2004-000853, and a part of the disclosure of these documents is incorporated herein by reference and the compounds are described herein. (Definition) Hereinafter, terms commonly used in this specification will be described. Unless otherwise specified, each term is used in the meaning described below.

[0013] The alkyl group means an unsubstituted alkyl group and an alkyl group substituted with a halogen atom, an amino group, a mercapto group, etc., and includes both a linear alkyl group and a cyclic alkyl group (cycloalkyl group). The alkyl group may have a branch. The number of carbon atoms of the alkyl group is usually 1 to 20, preferably 1 to 15, more preferably about 1 to 10. Specifically, methyl group, ethyl group, propyl group, i-propyl group, butyl group, i-butyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, lauryl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, trifluoropropyl group, tridecafluoro-1,1,2,2-tetrahydrooctyl group, heptadecafluoro-1,1,2,2-tetrahydrodecyl group, aminopropyl group, aminooctyl group, aminodecyl group, mercaptopropyl group, mercaptooctyl group, mercapto decyl group, etc. are exemplified. Examples of the C1-C12 alkyl group include, for example, methyl group, ethyl group, propyl group, i-propyl group, butyl group, i-butyl group, s-butyl group, t-butyl group, pentyl group, isoamyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, etc.

[0014] The alkoxy group means an unsubstituted alkoxy group and an alkoxy group substituted with a halogen atom, an alkoxy group, etc., and includes both a linear alkoxy group and a cyclic alkoxy group (cycloalkoxy group). The alkoxy group may have a branch. The number of carbon atoms in the alkoxy group is usually from 1 to 20, preferably from 1 to 15, more preferably about 1 to 10. Specifically, methoxy group, ethoxy group, propyloxy group, i-propyloxy group, butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyloxy group, perfluorooctyloxy group, methoxymethyloxy group, 2-methoxyethyloxy group, etc. are exemplified. Examples of the C1-C12 alkoxy group include, for example, methoxy group, ethoxy group, propyloxy group, i-propyloxy group, butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, etc.

[0015] The acyl group means an unsubstituted acyl group and an acyl group substituted with a halogen atom, etc. The number of carbon atoms in the acyl group is usually from 1 to 20, preferably from 2 to 18, more preferably about 2 to 16. Examples of the acyl group include, for example, formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group, benzoyl group, trifluoroacetyl group, pentafluorobenzoyl group, etc.

[0016] The acyloxy group means an unsubstituted acyloxy group and an acyloxy group substituted with a halogen atom or the like. The number of carbon atoms of the acyloxy group is usually 1 to 20, preferably 2 to 18, more preferably about 2 to 16. Examples of the acyloxy group include a formyloxy group, an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, a pentafluorobenzoyloxy group, and the like.

[0017] The amide group means an unsubstituted amide group and an amide group substituted with a halogen atom or the like. The number of carbon atoms of the amide group is usually 2 to 20, preferably 2 to 18, more preferably about 2 to 16. Examples of the amide group include a formamide group, an acetamide group, a propioamide group, a butyramide group, a benzamide group, a trifluoroacetamide group, a pentafluorobenzamide group, a diformamide group, a diacetamide group, a dipropioamide group, a dibutyramide group, a dibenzamide group, a ditrifluoroacetamide group, a dipentafluorobenzamide group, and the like.

[0018] The alkenyl group is an alkenyl group having 2 to carbon atoms, and examples thereof include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 1-octenyl group, and the like.

[0019] The alkynyl group is an alkynyl group having 2 to carbon atoms, and examples thereof include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 1-hexynyl group, a 2-hexynyl group, a 1-octynyl group, and the like.

[0020] The alkylthio group means an unsubstituted alkylthio group and an alkylthio group substituted with a halogen atom or the like, and includes both a linear alkylthio group and a cyclic alkylthio group (cycloalkylthio group). The alkylthio group may have a branch. The number of carbon atoms of the alkylthio group is usually from 1 to 20, preferably from 1 to 15, more preferably about 1 to 10. Specifically, methylthio group, ethylthio group, propylthio group, i-propylthio group, butylthio group, i-butylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, laurylthio group, trifluoromethylthio group and the like can be exemplified. Examples of the C1-C12 alkylthio group include, for example, methylthio group, ethylthio group, propylthio group, i-propylthio group, butylthio group, i-butylthio group, s-butylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, laurylthio group and the like.

[0021] The aryl group is a group remaining after removing one hydrogen atom bonded to a carbon atom constituting an aromatic ring from an aromatic hydrocarbon, and means an unsubstituted aryl group and an aryl group substituted with a halogen atom, an alkoxy group, an alkyl group or the like. The aryl group includes those having a benzene ring, those having a condensed ring, and those in which two or more independent benzene rings or condensed rings are bonded via a single bond or a divalent group such as an alkenylene group such as a vinylene group. The number of carbon atoms of the aryl group is usually from 6 to 60, preferably from 7 to 48, more preferably about 7 to 30. Examples of the aryl group include phenyl group, C1-C12 alkoxyphenyl group, C1-C12 alkylphenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, pentafluorophenyl group and the like, and C1-C12 alkoxyphenyl group and C1-C12 alkylphenyl group are preferred.

[0022] Specific examples of the C1-C12 alkoxyphenyl group include a methoxyphenyl group, an ethoxyphenyl group, a propyloxyphenyl group, an i-propyloxyphenyl group, a butoxyphenyl group, an i-butoxyphenyl group, an s-butoxyphenyl group, a t-butoxyphenyl group, a pentyloxyphenyl group, a hexyloxyphenyl group, a cyclohexyloxyphenyl group, a heptyloxyphenyl group, an octyloxyphenyl group, a 2-ethylhexyloxyphenyl group, a nonyloxyphenyl group, a decyloxyphenyl group, a 3,7-dimethyloctyloxyphenyl group, a lauryloxyphenyl group, and the like.

[0023] Specific examples of the C1-C12 alkylphenyl group include a methylphenyl group, an ethylphenyl group, a dimethylphenyl group, a propylphenyl group, a mesityl group, a methylethylphenyl group, an i-propylphenyl group, a butylphenyl group, an i-butylphenyl group, an s-butylphenyl group, a t-butylphenyl group, a pentylphenyl group, an isoamylphenyl group, a hexylphenyl group, a heptylphenyl group, an octylphenyl group, a nonylphenyl group, a decylphenyl group, a dodecylphenyl group, and the like.

[0024] The aryloxy group means an unsubstituted aryloxy group and an aryloxy group substituted with a halogen atom, an alkoxy group, an alkyl group, etc. The number of carbon atoms of the aryloxy group is usually 6 to 60, preferably 7 to 48, more preferably about 7 to 30. Specific examples thereof include a phenoxy group, a C1-C12 alkoxyphenoxy group, a C1-C12 alkylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a pentafluorophenyloxy group, etc., and a C1-C12 alkoxyphenoxy group and a C1-C12 alkylphenoxy group are preferred.

[0025] Specific examples of the C1-C12 alkoxyphenoxy group include a methoxyphenoxy group, an ethoxyphenoxy group, a propyloxyphenoxy group, an i-propyloxyphenoxy group, a butoxyphenoxy group, an i-butoxyphenoxy group, an s-butoxyphenoxy group, a t-butoxyphenoxy group, a pentyloxyphenoxy group, a hexyloxyphenoxy group, a cyclohexyloxyphenoxy group, a heptyloxyphenoxy group, an octyloxyphenoxy group, a 2-ethylhexyloxyphenoxy group, a nonyloxyphenoxy group, a decyloxyphenoxy group, a 3,7-dimethyloctyloxyphenoxy group, a lauryloxyphenoxy group, and the like.

[0026] Specific examples of the C1-C12 alkylphenoxy group include a methylphenoxy group, an ethylphenoxy group, a dimethylphenoxy group, a propylphenoxy group, a 1,3,5-trimethylphenoxy group, a methylethylphenoxy group, an i-propylphenoxy group, a butylphenoxy group, an i-butylphenoxy group, an s-butylphenoxy group, a t-butylphenoxy group, a pentylphenoxy group, an isoamylphenoxy group, a hexylphenoxy group, a heptylphenoxy group, an octylphenoxy group, a nonylphenoxy group, a decylphenoxy group, a dodecylphenoxy group, and the like.

[0027] The arylthio group means an unsubstituted arylthio group and an arylthio group substituted with a halogen atom, an alkoxy group, an alkyl group, or the like. The number of carbon atoms of the arylthio group is usually 6 to 60, preferably 7 to 48, and more preferably about 7 to 30. Specific examples include a phenylthio group, a C1-C12 alkoxyphenylthio group, a C1-C12 alkylphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a pentafluorophenylthio group, and the like.

[0028] The arylalkyl group means an unsubstituted arylalkyl group and an arylalkyl group substituted with a halogen atom, an alkoxy group, an alkyl group, or the like. The number of carbon atoms of the arylalkyl group is usually 7 to 60, preferably 7 to 48, and more preferably about 7 to 30. Specifically, examples include phenyl-C1-C12 alkyl groups, C1-C12 alkoxyphenyl-C1-C12 alkyl groups, C1-C12 alkylphenyl-C1-C12 alkyl groups, 1-naphthyl-C1-C12 alkyl groups, 2-naphthyl-C1-C12 alkyl groups, and the like.

[0029] The arylalkoxy group means an unsubstituted arylalkoxy group and an arylalkoxy group substituted with a halogen atom, an alkoxy group, an alkyl group, or the like. The number of carbon atoms in the arylalkoxy group is usually 7 to 60, preferably 7 to 48, more preferably about 7 to 30. Specifically, examples include phenyl-C1-C12 alkoxy groups, C1-C12 alkoxyphenyl-C1-C12 alkoxy groups, C1-C12 alkylphenyl-C1-C12 alkoxy groups, 1-naphthyl-C1-C12 alkoxy groups, 2-naphthyl-C1-C12 alkoxy groups, and the like.

[0030] The arylalkylthio group means an unsubstituted arylalkylthio group and an arylalkylthio group substituted with a halogen atom, an alkoxy group, an alkyl group, or the like. The number of carbon atoms in the arylalkylthio group is usually 7 to 60, preferably 7 to 48, more preferably about 7 to 30. Specifically, examples include phenyl-C1-C12 alkylthio groups, C1-C12 alkoxyphenyl-C1-C12 alkylthio groups, C1-C12 alkylphenyl-C1-C12 alkylthio groups, 1-naphthyl-C1-C12 alkylthio groups, 2-naphthyl-C1-C12 alkylthio groups, and the like.

[0031] The arylalkenyl group means an unsubstituted arylalkenyl group and an arylalkenyl group substituted with a halogen atom, an alkoxy group, an alkyl group, etc. The number of carbon atoms of the arylalkenyl group is usually 8 to 60, preferably 8 to 48, more preferably about 8 to 30. Specific examples thereof include phenyl-C2-C12 alkenyl group, C1-C12 alkoxyphenyl-C2-C12 alkenyl group, C1-C12 alkylphenyl-C2-C12 alkenyl group, 1-naphthyl-C2-C12 alkenyl group, 2-naphthyl-C2-C12 alkenyl group, etc., and C1-C12 alkoxyphenyl-C2-C12 alkenyl group and C2-C12 alkylphenyl-C2-C12 alkenyl group are preferred.

[0032] Examples of the C2-C12 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 1-pentenyl group, 2-pentenyl group, 1-hexenyl group, 2-hexenyl group, 1-octenyl group, etc.

[0033] The arylalkynyl group means an unsubstituted arylalkynyl group and an arylalkynyl group substituted with a halogen atom, an alkoxy group, an alkyl group, etc. The number of carbon atoms of the arylalkynyl group is usually 8 to 60, preferably 8 to 48, more preferably about 8 to 30. Specific examples thereof include phenyl-C2-C12 alkynyl group, C1-C12 alkoxyphenyl-C2-C12 alkynyl group, C1-C12 alkylphenyl-C2-C12 alkynyl group, 1-naphthyl-C2-C12 alkynyl group, 2-naphthyl-C2-C12 alkynyl group, etc., and C1-C12 alkoxyphenyl-C2-C12 alkynyl group and C1-C12 alkylphenyl-C2-C12 alkynyl group are preferred.

[0034] Examples of the C2-C12 alkynyl group include an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 1-pentynyl group, 2-pentynyl group, 1-hexynyl group, 2-hexynyl group, 1-octynyl group, etc.

[0035] The monovalent heterocyclic group refers to the remaining atomic group obtained by removing one hydrogen atom from a heterocyclic compound, and means an unsubstituted monovalent heterocyclic group and a monovalent heterocyclic group substituted with a substituent such as an alkyl group. The number of carbon atoms in the monovalent heterocyclic group, excluding the number of carbon atoms in the substituent, is usually about 3 to 60, preferably 3 to 30, more preferably 3 to 20. Here, the heterocyclic compound refers to an organic compound having a cyclic structure, among which, as the elements constituting the ring, not only carbon atoms but also heteroatoms such as oxygen atoms, sulfur atoms, nitrogen atoms, phosphorus atoms, boron atoms, silicon atoms, selenium atoms, tellurium atoms, and arsenic atoms are included. Among the monovalent heterocyclic groups, a monovalent aromatic heterocyclic group is preferred. Examples of the monovalent heterocyclic group include a thienyl group, a C1-C12 alkylthienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a C1-C12 alkylpyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a pyrrolidyl group, a piperidyl group, a quinolyl group, an isoquinolyl group, etc. Among them, a thienyl group, a C1-C12 alkylthienyl group, a pyridyl group, and a C1-C12 alkylpyridyl group are preferred.

[0036] The heterocyclic thio group means a group in which the hydrogen atom of the mercapto group is substituted with a monovalent heterocyclic group. Examples of the heterocyclic thio group include heteroarylthio groups such as a pyridylthio group, a pyridazinylthio group, a pyrimidinylthio group, a pyrazinylthio group, and a triazinylthio group.

[0037] The amino group means an unsubstituted amino group and an amino group substituted with one or two substituents selected from an alkyl group, an aryl group, an arylalkyl group, and a monovalent heterocyclic group (hereinafter referred to as a substituted amino group). The substituent may further have a substituent (hereinafter sometimes referred to as a secondary substituent). The number of carbon atoms of the substituted amino group, excluding the number of carbon atoms of the secondary substituent, is usually 1 to 60, preferably 2 to 48, more preferably about 2 to 40. Examples of the substituted amino group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a propylamino group, a dipropylamino group, an isopropylamino group, a diisopropylamino group, a butylamino group, an isobutylamino group, an s-butylamino group, a t-butylamino group, a pentylamino group, a hexylamino group, a heptylamino group, an octylamino group, a 2-ethylhexylamino group, a nonylamino group, a decylamino group, a 3,7-dimethyloctylamino group, a dodecylamino group, a cyclopentylamino group, a dicyclopentylamino group, a cyclohexylamino group, a dicyclohexylamino group, a ditrifluoromethylamino group, a phenylamino group, a diphenylamino group, a C1-C12 alkoxyphenylamino group, a di(C1-C12 alkoxyphenyl)amino group, a C1-C12 alkylphenylamino group, a di(C1-C12 alkylphenyl)amino group, a 1-naphthylamino group, a 2-naphthylamino group, a pentafluorophenylamino group, a pyridylamino group, a pyridazinylamino group, a pyrimidylamino group, a pyrazinylamino group, a triazinylamino group, a phenyl-C1-C12 alkylamino group, a C1-C12 alkoxyphenyl-C1-C12 alkylamino group, a di(C1-C12 alkoxyphenyl-C1-C12 alkyl)amino group, a C1-C12 alkylphenyl-C1-C12 alkylamino group, a di(C1-C12 alkylphenyl-C1-C12 alkyl)amino group, a 1-naphthyl-C1-C12 alkylamino group, a 2-naphthyl-C1-C12 alkylamino group, and the like.

[0038] The silyl group means an unsubstituted silyl group and a silyl group substituted with one, two or three substituents selected from an alkyl group, an aryl group, an arylalkyl group and a monovalent heterocyclic group (hereinafter referred to as a substituted silyl group). The substituent may have a secondary substituent. The number of carbon atoms of the substituted silyl group, excluding the number of carbon atoms of the secondary substituent, is usually 1 to 60, preferably 3 to 48, more preferably about 3 to 40. Examples of the substituted silyl group include a trimethylsilyl group, a triethylsilyl group, a tripropylsilyl group, a tri-isopropylsilyl group, a dimethyl-isopropylsilyl group, a diethyl-isopropylsilyl group, a t-butylsilyldimethylsilyl group, a pentyldimethylsilyl group, a hexyldimethylsilyl group, a heptyldimethylsilyl group, an octyldimethylsilyl group, a 2-ethylhexyl-dimethylsilyl group, a nonyldimethylsilyl group, a decyldimethylsilyl group, a 3,7-dimethyloctyl-dimethylsilyl group, a dodecyldimethylsilyl group, a phenyl-C1-C12 alkylsilyl group, a C1-C12 alkoxyphenyl-C1-C12 alkylsilyl group, a C1-C12 alkylphenyl-C1-C12 alkylsilyl group, a 1-naphthyl-C1-C12 alkylsilyl group, a 2-naphthyl-C1-C12 alkylsilyl group, a phenyl-C1-C12 alkyldimethylsilyl group, a triphenylsilyl group, a tri-p-xylylsilyl group, a tribenzylsilyl group, a diphenylmethylsilyl group, a t-butyldiphenylsilyl group, a dimethylphenylsilyl group and the like.

[0039] The acyl group means an unsubstituted acyl group and an acyl group substituted with a halogen atom or the like. The number of carbon atoms of the acyl group is usually 1 to 20, preferably 2 to 18, more preferably about 2 to 16. Examples of the acyl group include a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, a benzoyl group, a trifluoroacetyl group, a pentafluorobenzoyl group and the like.

[0040] The acyloxy group means an unsubstituted acyloxy group and an acyloxy group substituted with a halogen atom or the like. The number of carbon atoms in the acyloxy group is usually from 1 to 20, preferably from 2 to 18, more preferably about 2 to 16. Examples of the acyloxy group include a formyloxy group, an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, a pentafluorobenzoyloxy group and the like.

[0041] The imine residue means a residue obtained by removing one hydrogen atom from the structure in an imine compound having a structure represented by at least one of the formula: H-N=C< and the formula: -N=CH-. Examples of such imine compounds include aldimines, ketimines, and compounds in which the hydrogen atom bonded to the nitrogen atom in the aldimine is substituted with an alkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, an arylalkynyl group or the like. The number of carbon atoms in the imine residue is usually from 2 to 20, preferably from 2 to 18, more preferably about 2 to 16. Examples of the imine residue include a group represented by the general formula: -CR’=N-R’’ or the general formula: -N=C(R’’)2 (wherein R’ represents a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, an arylalkynyl group, and R’’ are the same or different and represent an alkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, an arylalkynyl group, provided that when two R’’ are present, the two R’’ are bonded to each other to form a divalent group, for example, an alkylene group having 2 to 18 carbon atoms such as an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, etc. to form a ring).

[0042] The acid imide group means a residue obtained by removing the hydrogen atom bonded to the nitrogen atom from the acid imide. The number of carbon atoms in the acid imide group is usually from 4 to 20, preferably from 4 to 18, more preferably about 4 to 16.

[0043] The carboxy group means an unsubstituted carboxy group and a carboxyl group substituted with a substituent such as an alkyl group, an aryl group, an arylalkyl group, or a monovalent heterocyclic group (hereinafter referred to as a substituted carboxy group). The substituent may have a secondary substituent. The number of carbon atoms of the substituted carboxy group, excluding the number of carbon atoms of the secondary substituent, is usually 1 to 60, preferably 2 to 48, more preferably about 2 to 45. Examples of the substituted carboxy group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, an s-butoxycarbonyl group, a t-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a cyclohexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a 3,7-dimethyloctyloxycarbonyl group, a dodecyloxycarbonyl group, a trifluoromethoxycarbonyl group, a pentafluoroethoxycarbonyl group, a perfluorobutoxycarbonyl group, a perfluorohexyloxycarbonyl group, a perfluorooctyloxycarbonyl group, a phenoxycarbonyl group, a naphthoxycarbonyl group, a pyridyloxycarbonyl group, and the like.

[0044] The aromatic hydrocarbon group of X valence means an atomic group formed by removing X hydrogen atoms from an aromatic hydrocarbon, and includes those having an independent benzene ring or condensed ring. The aromatic hydrocarbon group usually has about 6 to 60 carbon atoms, preferably 6 to 48 carbon atoms, more preferably 6 to 30 carbon atoms, and still more preferably 6 to 18 carbon atoms. The number of carbon atoms does not include the carbon atoms of the substituent. Specific examples of the aromatic hydrocarbon group include, for example, in the case of a divalent aromatic hydrocarbon group (arylene group), unsubstituted or substituted phenylene groups such as 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, etc.; unsubstituted or substituted naphthalenediyl groups such as 1,4-naphthalenediyl group, 1,5-naphthalenediyl group, 2,6-naphthalenediyl group, etc.; unsubstituted or substituted anthracenediyl groups such as 1,4-anthracenediyl group, 1,5-anthracenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, etc.; unsubstituted or substituted phenanthrenediyl groups such as 2,7-phenanthrenediyl group, etc.; unsubstituted or substituted naphthacenediyl groups such as 1,7-naphthacenediyl group, 2,8-naphthacenediyl group, 5,12-naphthacenediyl group, etc.; unsubstituted or substituted fluorenediyl groups such as 2,7-fluorenediyl group, 3,6-fluorenediyl group, etc.; unsubstituted or substituted pyrenediyl groups such as 1,6-pyrenediyl group, 1,8-pyrenediyl group, 2,7-pyrenediyl group, 4,9-pyrenediyl group, etc.; unsubstituted or substituted perylenediyl groups such as 3,9-perylenediyl group, 3,10-perylenediyl group, etc. Among them, preferably, they are unsubstituted or substituted phenylene groups and unsubstituted or substituted fluorenediyl groups.

[0045] The polyvalent heterocyclic group of X valence refers to the remaining atomic group obtained by removing X hydrogen atoms from a heterocyclic compound, and the number of carbon atoms is usually about 4 to 60, preferably 4 to 30, and particularly preferably 6 or more. The number of carbon atoms does not include the carbon atoms of the substituent. Specific examples of the polyvalent heterocyclic group of X valence include, for example, in the case of a divalent heterocyclic group, unsubstituted or substituted pyridinediyl groups such as 2,5-pyridinediyl group and 2,6-pyridinediyl group; unsubstituted or substituted thiophenediyl groups such as 2,5-thiophenediyl group; unsubstituted or substituted furandiyl groups such as 2,5-furandiyl group; unsubstituted or substituted quinolinediyl groups such as 2,6-quinolinediyl group; unsubstituted or substituted isoquinolinediyl groups such as 1,4-isoquinolinediyl group and 1,5-isoquinolinediyl group; unsubstituted or substituted quinoxalinediyl groups such as 5,8-quinoxalinediyl group; unsubstituted or substituted benz[1,2,5]thiadiazolediy groups such as 4,7-benz[1,2,5]thiadiazolediy group; unsubstituted or substituted benzothiazolediy groups such as 4,7-benzothiazolediy group; unsubstituted or substituted carbazolediy groups such as 2,7-carbazolediy group and 3,6-carbazolediy group; unsubstituted or substituted phenoxazinediyl groups such as 3,7-phenoxazinediyl group; unsubstituted or substituted phenothiazinediyl groups such as 3,7-phenothiazinediyl group; unsubstituted or substituted dibenzosilolediyl groups such as 2,7-dibenzosilolediyl group, etc. are mentioned, and preferably, unsubstituted or substituted benz[1,2,5]thiadiazolediy group, unsubstituted or substituted phenoxazinediyl group, unsubstituted or substituted phenothiazinediyl group.

[0046] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0047] (Photo- or thermoresponsive cleavage substrate) One aspect of the present invention relates to a photo- or thermoresponsive cleavage substrate having a first substrate and a cleavage molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, wherein the cleavage molecular layer is formed from a compound represented by any one of formulas (I) to (VII). The cleavage molecular layer contains a compound represented by any of the following formulas (I) to (VII): [Chemical formula] [Chemical formula] (In formulas (I) to (VII), Ra represents a group represented by the following formula (A), a group capable of forming an acid-base interaction with the group represented by the following formula (A), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Ra may be the same or different. Also, adjacent Ra may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Ra is a group represented by the following formula (A), a carboxy group, a sulfonyl group, or an amino group).

[0048] In a preferred embodiment, in formulas (I) to (VII), Ra is preferably a non-bulky group that does not inhibit the cleavage reaction and the subsequent dimerization reaction, and specifically, a hydrogen atom, a methyl group, or an ethyl group can be mentioned. Also, when Ra is a group represented by the following formula (A), its position is not limited, and a preferred position can be selected according to the use and the desired properties.

[0049] When Ra of the compound represented by any one of formulas (I) to (VII) has a group represented by the following formula (A), it can be bonded to the first substrate through the group represented by the formula (A). When Ra of the compound represented by any one of formulas (I) to (VII) has a group capable of forming an acid-base interaction such as a carboxy group, a sulfonyl group, or an amino group, it can be bonded to the first substrate through the acid-base interaction between the group capable of forming the acid-base interaction and the molecules on the surface of the first substrate. As the group capable of forming the acid-base interaction, a basic group can be employed when an acidic group is present on the first substrate, and an acidic group can be employed when a basic group is present on the first substrate. When the group capable of forming the acid-base interaction is an acidic group, a carboxy group or a sulfonyl group is preferable, and when it is a basic group, an amino group is preferable.

Chemical formula

[0050] In a preferred embodiment, in formula (A), Z is -C(=O)N(Rz)-, -N(Rz)C(=O)-. Ry1 is a halogen atom, a hydroxy group, an alkoxy group. Ry2 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms. Ak is an alkylene group having 1 to 6 carbon atoms. la is 1, and na is an integer of 1 to 3.)

[0051] In formulas (I) to (VII), Rb is a group represented by the following formula (B), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group, or an acrylate group. A plurality of Rb's may be the same or different. Adjacent Rb's may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocyclic ring, and these rings may have substituents. However, at least one of Rb's is a group represented by the following formula (B), an amino group, a carboxy group, or a sulfonyl group.

[0052] In a preferred embodiment, in formulas (I) to (VII), Rb is preferably a bulky group that does not inhibit the cleavage reaction and the subsequent dimerization reaction, and specifically, a hydrogen atom, a methyl group, or an ethyl group can be mentioned. When Rb is a group represented by the following formula (B), its position is not limited, and a preferred position can be selected according to the use and the desired properties.

[0053] In another embodiment, when Rb of the compound represented by any of formulas (I) to (VII) has a group represented by the following formula (B), it can be bonded to a second substrate or a material layer through the group represented by formula (B). When Rb of the compound represented by any of formulas (I) to (VII) has a group capable of forming an acid-base interaction such as a carboxy group, a sulfonyl group, or an amino group, it can be bonded to the second substrate through the acid-base interaction between the group capable of forming an acid-base interaction and the molecules on the surface of the second substrate. As the group capable of forming an acid-base interaction, a basic group can be employed when an acidic group is present on the second substrate, and an acidic group can be employed when a basic group is present on the second substrate. When the group capable of forming an acid-base interaction is an acidic group, a carboxy group or a sulfonyl group is preferred, and when it is a basic group, an amino group is preferred.

Chemical formula

[0054] In a preferred embodiment, in formula (B), -C(=O)O- and -OC(=O)- are preferred as Z. A halogen atom, a hydroxy group and an alkoxy group are preferred as Ry1. An alkylene group having 1 to 6 carbon atoms is preferred as Ak. 1 is preferred as la. An integer of 1 to 3 is preferred as na.)

[0055] Here, in one embodiment of the photo- or thermo-responsive cleavage base material of the present invention, Ra and Rb in the formula do not have a water-repellent group. In such an embodiment, Ra and Rb in the formula do not contain a fluorine atom.)

[0056] In another embodiment of the photo- or thermo-responsive cleavage substrate of the present invention, the compound forming the cleavage molecular layer can be a compound having an anthracene structure represented by the following formula (I). [Chemical formula] (Ra and Rb in the formula represent the same as those defined above.)

[0057] In a more preferred embodiment of the photo- or thermo-responsive cleavage substrate of the present invention, the compound having a cleavage molecular layer is a compound represented by the following formula (I-a) or (I-b). [Chemical formula] [Chemical formula]

[0058] The "first substrate" that can be used in the present invention is not particularly limited as long as it can have a cleavage molecular layer on the substrate surface. Examples of the first substrate include metal substrates such as glass, silicon wafers, and aluminum.

[0059] The "photo- or thermo-responsive cleavage substrate" according to the present invention has a cleavage molecular layer on a part or the whole of the surface of the first substrate. The "photo- or thermo-responsive cleavage substrate" has a cleavage molecular layer that can reversibly perform cleavage and bonding in response to light or heat stimuli.

[0060] The photo- or thermo-responsive cleavage substrate having a cleavage molecular layer can be produced, for example, as follows. One embodiment of the method for producing a photo- or thermo-responsive cleavage substrate is to form a molecular layer containing a compound (i) represented by the following formula (i) on the surface of the first substrate, and then subject the compound (i) represented by the following formula (i) and the compound (ii) represented by the following formula (ii) to a dimerization reaction on the surface of the first substrate. [Chemical formula] (In formula (i), Ra is the same as the definition of Ra in formulas (I) to (VII). n1 represents an integer of 0 or more.) [Chemical formula] (In formula (ii), Rb is the same as the definition of Rb in formulas (I) to (VII). n2 represents an integer of 0 or more.) Note that n1 and n2 in formulas (i) and (ii) are preferably integers from 0 to 4.

[0061] As the functional group used for dimerization, a group having a double bond capable of undergoing a photo-dimerization reaction or an aromatic condensed ring having a site capable of undergoing a photo-dimerization reaction is preferably used. Among them, the aromatic condensed ring group is more preferably used because it absorbs light with relatively low energy. Specific examples of the preferably used functional groups include a group having a cinnamic acid ester structure, a group having a chalcone structure, a group having a styrylpyridinium structure, a group having an α-phenylmaleimide structure, an anthryl group, a group having a coumarin structure, and the like.

[0062] Further, as another embodiment of the method for producing a photo- or thermo-responsive cleavage base material, compound (i) represented by the following formula (i) and compound (ii) represented by the following formula (ii) may be dimerized in advance, and a cleavage molecular layer may be formed on the surface of the first base material using the dimerized compound.

[0063] The method of the dimerization reaction can be carried out by irradiation with light. The light used for light irradiation is not particularly limited as long as it is in the wavelength region where the compound absorbs the light energy and causes a dimerization reaction. For example, light having a wavelength of 200 nm or more and around 400 nm is preferable. Since light of less than 200 nm has very strong energy, it may cause decomposition of the base material or the compound. In particular, light in the vicinity of 300 to 410 nm, which is effective for many glasses and transparent plastics with expected transparency, is effective. The irradiation time is appropriately changed according to the wavelength of the light, the intensity of the light, the type of the light source, the type of the compound, and the like.

[0064] Examples of the light source include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, LED lamps, xenon lamps, sodium lamps, gas lasers such as nitrogen, liquid lasers of organic dye solutions, solid lasers containing rare earth ions in inorganic single crystals, and the like. Further, as a light source other than a laser that can obtain monochromatic light, light of a specific wavelength extracted using an optical filter such as a band-pass filter or a cut-off filter for a broadband line spectrum or a continuous spectrum may be used. Since a large area can be irradiated at once, a high-pressure mercury lamp or an ultra-high-pressure mercury lamp is preferable as the light source.

[0065] In one embodiment, the light or heat-responsive cleavage substrate of the present invention further includes a first material layer. The light or heat-responsive cleavage substrate of the present invention can further include a first material layer preferable according to its use. The first material layer can be formed on the cleavage molecular layer. Thereby, by promoting the cleavage reaction in the cleavage molecular layer, it is possible to separate the first substrate and the first material layer via the cleavage molecular layer. The material for forming the first material layer is not limited as long as the material layer can be formed on the cleavage molecular layer, and examples thereof include adhesives, inks, plastic films, metal substrates, and the like. As a method for forming the material layer on the cleavage molecular layer, a known preferable method can be appropriately adopted according to the material used.

[0066] In one embodiment, the light or heat-responsive cleavage substrate of the present invention includes a first material layer on the cleavage molecular layer, the first material layer is an adhesive layer containing an adhesive, and further has a second substrate on the adhesive layer. The "second substrate" that can be used in the present invention is not limited as long as it can be combined with the adhesive layer to form a light or heat-responsive cleavage substrate. Examples of the second substrate include metal substrates such as glass, silicon wafers, and aluminum.

[0067] In another aspect of the present invention, there is provided a method for cleaving the cleavage molecular layer in a photo- or thermo-responsive cleavage substrate, the method comprising the step of applying light or heat to the cleavage molecular layer. By cleavage of the cleavage molecular layer, a part of the first substrate and the cleavage molecular layer can be dissociated. In an embodiment having a first adhesive layer or a second substrate on the cleavage molecular layer, cleavage of the cleavage molecular layer can dissociate the first substrate and the first adhesive layer and / or the second substrate. The light used for light irradiation for cleavage of the cleavage molecular layer is not particularly limited as long as it is in a wavelength range in which the cleavage molecular layer absorbs the light energy and causes a cleavage reaction. For example, light having a wavelength of 200 nm or more and 300 nm or less is preferable. Since light having a wavelength of less than 200 nm has very strong energy, it may cause decomposition of the substrate or compound. Also, light having a wavelength longer than 300 nm is likely to be light in a region that the compound does not absorb. The irradiation time is appropriately changed according to the wavelength of the light, the intensity of the light, the type of light source, the type of the compound, and the like. As the light source, a light source that can be used for the dimerization reaction can be similarly adopted.

[0068] When performing the cleavage reaction by heating, it is not particularly limited as long as it is the amount of heat that the cleavage molecular layer absorbs the heat energy and causes the cleavage reaction. For example, the conditions can be 120 to 180 °C for 5 minutes to 3 hours. The heating time is appropriately changed according to temperature conditions and the like. The apparatus that can be used for heating is also not limited as long as it can promote cleavage of the cleavage molecular layer. For example, there are a method of warming the whole by heat conduction using a hot stage and a method of local heating using electromagnetic waves such as infrared rays, microwaves, and white light.

[0069] Another aspect of the present invention provides a method for adhering a cleaved cleavage molecular layer, the method comprising the step of applying light to the cleaved cleavage molecular layer. Specifically, by performing light irradiation for dimerization in a state where the compound (i) represented by the above formula (i) that formed the cleavage molecular layer and the compound (ii) represented by the above formula (ii) are in contact, a cleaved cleavage molecular layer composed of the compound (i) and the compound (ii) can be formed again. Thereby, by reforming the cleavage molecular layer, a part of the first substrate and the cleavage molecular layer can be bonded. In an embodiment having the first adhesive layer or the second substrate on the cleavage molecular layer, by reforming the cleavage molecular layer, the first substrate can be bonded to the first adhesive layer and / or the second substrate. The conditions for light irradiation for dimerization can be the same as the conditions for light irradiation for dimerization in the method for producing the above-mentioned light or heat-responsive cleavage substrate.

[0070] Hereinafter, the present invention will be described in detail using specific examples, but the present invention is not limited to the following embodiments.

Example

[0071] (Example 1-1. Formation of a cleavage molecular layer containing a photo-dimerization structure 1) In this example, the preparation of a dimerization compound composed of the compound (Compound 1) represented by the following formula (i-i) and the compound (Compound 2) represented by the following formula (ii-i) and the thermal decomposition of the dimerization compound were confirmed.

Chemical formula

[0072] A glass substrate having a molecular layer composed of the above Compound 1 on its surface was prepared as follows. First, the glass substrate was ultrasonically cleaned with a cleaning solution (Extran 2% aqueous solution) for 3 hours. Then, the glass substrate was ultrasonically cleaned with ultrapure water for 20 minutes 4 times. After cleaning, the glass substrate was immersed in a 10% ethanol solution of potassium hydroxide overnight. After immersion, the glass substrate was ultrasonically cleaned with ultrapure water for 20 minutes 4 times. Then, the glass substrate was dried under reduced pressure for 1 hour.

[0073] Next, Compound 1 shown in the above formula (i) was dissolved in an equal - volume mixed solvent of dehydrated dichloroethylene and dehydrated toluene to a concentration of 4 mmol / L. The washed glass substrate was immersed in the obtained solution for 1 hour. Thereafter, the glass substrate was taken out and dried in an oven set at 110 °C for 30 minutes. After drying, the operation of immersing the glass substrate in a chloroform solution was repeated 3 times to remove the excess Compound 1, and a molecular layer containing Compound 1 was formed on the glass substrate. The formation of the molecular layer containing Compound 1 was confirmed from the absorption peak derived from anthracene monomer by ultraviolet - visible absorption spectrum measurement (Figure 1).

[0074] Compound 2 was dissolved in a chloroform solution to a concentration of 1 mmol / L. The glass substrate having a molecular layer containing Compound 1 on its surface was immersed in the obtained solution, and shaken in a shaking bath set at 40 °C for 30 minutes. Thereafter, the glass substrate was taken out and dried in an oven set at 80 °C for 30 minutes. In this way, a molecular layer containing Compound 2 was formed on the molecular layer containing Compound 1.

[0075] Next, light with a wavelength of 405 nm was irradiated onto this substrate at an intensity of 5 mW / cm 2 for 20 minutes to dimerize and bond the anthracene structure of Compound 1 and the anthracene structure of Compound 2. After irradiation, the operation of immersing the glass substrate in a chloroform solution was repeated 3 times to remove the excess Compound 2. In the light - irradiated part, due to the photo - dimerization reaction of Compound 1 and Compound 2, a molecular layer composed of the compound shown in the following formula (I - a) (Compound 3) was formed on the glass substrate.

Chemical formula

[0076] (Example 1 - 2. Thermal decomposition of the cleavage molecular layer 1) A glass substrate having a molecular layer composed of Compound 3 obtained in Example 1-1 was allowed to stand on a hot plate at 160 °C for 30 minutes to thermally decompose the dimer of Compound 3 on the glass substrate and dissociate it into Compound 1 and Compound 2. After the heating step, since the absorption peak derived from anthracene monomer increased in the ultraviolet-visible absorption spectrum measurement, the progress of the thermal decomposition reaction was confirmed. Fig. 3 shows the change in the absorption spectrum before and after heating. Fig. 4 is a diagram schematically showing the cleavage of the dimer of Compound 1 and Compound 2 constituting the molecular layer into monomers by heating.

[0077] (Example 1-3. Thermal Decomposition 2 of Cleaved Molecular Layer) The thermal decomposition of the molecular layer was carried out in the same manner as in Example 2 except that the temperature condition for the thermal decomposition of the molecular layer in Example 1-2 was in the range of 100 to 180 °C, and its progress was measured. As a result, it was confirmed that the thermal decomposition of the molecular layer composed of Compound 3 proceeds at a temperature of 120 °C or higher.

[0078] (Example 1-4. Repeated Photo-Dimerization and Thermal Decomposition of Molecular Layer) In this example, it was confirmed whether the photo-dimerization and thermal decomposition of the molecular layer can be repeated. Specifically, under the same conditions as in Example 1-1, a layer composed of Compound 3 was formed on a glass substrate. Then, the thermal decomposition by heating and the photo-dimerization by light irradiation with a wavelength of 405 nm were repeatedly carried out under the same conditions as in Example 1-1 and Example 1-2. As a result, it was found that the photo-dimerization and thermal decomposition proceed repeatedly three or more times.

[0079] (Example 2-1. Formation 2 of Cleaved Molecular Layer Containing Photo-Dimerized Structure) The glass substrate was cleaned under the same conditions as in Example 1-1. The cleaned glass substrate was immersed in a solution in which Compound 4 represented by the following formula (iii) was dissolved to a concentration of 1 wt% with respect to dehydrated toluene for 1 hour. [Chemical formula]

[0080] Thereafter, the glass substrate was taken out and the operation of immersing it in a toluene solution was repeated three times to remove excess Compound 4, and then it was dried in an oven set at 120 °C for 30 minutes. Thereafter, the glass substrate was ultrasonically washed in the toluene solution for 1 minute to form a molecular layer composed of Compound 4 on the glass substrate.

[0081] Next, a dimer of Compound (Compound 5) represented by the following formula (iv) (represented by the following formula (v); Compound 6) was synthesized by a photo-dimerization reaction. Specifically, a solution in which Compound 5 was dissolved at a concentration of 50 g / L in tetrahydrofuran was irradiated with ultraviolet light having a wavelength of 365 nm at an intensity of 50 mW / cm 2 for 12 hours under a nitrogen atmosphere. The generated white crystals were collected by filtration. It was confirmed by 1H NMR that Compound 6 was generated by the photo-dimerization reaction. 1H NMR (DMSO-d6): δ = 6.89 (m, 4H), 6.82 (m, 8H), 6.77 (m, 4H), 5.63 (s, 2H)

Chemical formula

Chemical formula

[0082] Next, Compound 3 was bonded to the molecular layer on this glass substrate. Specifically, Compound 3 was dissolved in a toluene solution to a concentration of 0.1 mmol / L, the obtained solution was immersed with the glass substrate, and shaken in a shaking bath set at 40 °C for 30 minutes. Then, the glass substrate was taken out and dried in an oven set at 80 °C for 30 minutes. In this way, a molecular layer containing a compound in which Compound 3 is bonded to Compound 7 (the compound shown in Formula (I-b): Compound 8) was formed on the glass substrate. Compound 8 is a compound in any of the three bonding modes of the compound shown in Formula (I-b). Compound 8 includes a compound in at least one of the three forms of the compound shown in Formula (I-b). By this operation, since a layer containing Compound 3 having a silyl group exists on the substrate surface, it becomes a reactive surface. [Chemical formula]

[0083] (Example 2-2. Thermal decomposition of the cleavage molecular layer) In the glass substrate having the molecular layer composed of Compound 8 obtained in Example 2-1, thermal decomposition of the dimerized anthracene structure portion in Compound 8 was performed. Specifically, the thermal decomposition of the dimerized anthracene structure was carried out by leaving this glass substrate standing on a hot plate at 160 °C for 1 hour. From the increase in the absorption peak derived from anthracene monomer in the ultraviolet-visible absorption spectrum measurement, the progress of the thermal decomposition reaction was confirmed (Figure 5).

[0084] (Example 3-1. Photodissociation of the cleavage molecular layer) Using a glass substrate having a molecular layer composed of Compound 3, the photodissociation of the dimerized anthracene structure in Compound 3 was examined. Specifically, with respect to the glass substrate having the molecular layer composed of Compound 3 obtained in Example 1-1, light with a wavelength of 245 nm was irradiated at 0.5 mW / cm 2Irradiate at the intensity of for 2 minutes to photolyze the dimerized anthracene structure in Compound 3 and dissociate it into Compound 1 and Compound 2. After the photolysis operation, since the absorption peak derived from the anthracene monomer increased in the ultraviolet-visible absorption spectrum measurement, the progress of the photolysis reaction was confirmed. Fig. 6 shows the change in the absorption spectrum before and after irradiation with light of wavelength 254 nm.

[0085] (Example 3-2. Repetition of Photodimerization and Photolysis of Cleavable Molecular Layers) In this example, it was confirmed whether the photodimerization and thermal decomposition of the molecular layer could be repeated. Specifically, under the same conditions as in Example 1-1, a molecular layer composed of Compound 3 was formed on a glass substrate. Then, photolysis by irradiation with light of wavelength 245 nm and photodimerization by irradiation with light of wavelength 405 nm were repeatedly performed under the same conditions as in Example 1-1 and Example 3-1. As a result, it was found that photodimerization and photolysis proceeded repeatedly three or more times.

[0086] (Example 4-1. Measurement of Adhesion Strength of Cleavable Molecular Layers) In this example, the adhesion strength when the cleavable molecular layer of the present invention was formed between a base material and an adhesive layer was verified. As the compound for forming the cleavable molecular layer, the compound (Compound 9) represented by the following formula (I-c) was used. The compound represented by the following formula (I-c) was synthesized by the photodimerization reaction of Compound 1. Specifically, ultraviolet light of wavelength 405 nm was irradiated at an intensity of 50 mW / cm 2 to a solution in which Compound 1 was dissolved at a concentration of 95 g / L in tetrahydrofuran for 24 hours under a nitrogen atmosphere. The solvent in the filtrate collected by filtration was distilled off under reduced pressure. It was fractionated by column chromatography (silica gel, developing solvent: a mixed solvent of chloroform:ethyl acetate = 9:1). The formation of the following Compound 9 by the photodimerization reaction was confirmed by 1H NMR. 1H NMR (CDC l3): δ = 7.03 (m, 4H), 6.80 (m, 12H), 6.01 (s, 2H), 5.53 (s, 2H), 3.73 (m, 12H), 3.47 (m, 4H), 1.68 (m, 4H), 1.14 (m, 18H), 0.57 (t, 4H)

Chem.

[0087] As a result of the peeling test, the cleavage substrate having the cleavage molecular layer had a stronger adhesive strength than the substrate without the cleavage molecular layer (Figure 8). Further, when the substrate after the peeling test was observed, In the glass cleaning substrate without the cleavage molecular layer, peeling was observed at the interface between the glass substrate and the adhesive layer, and the adhesive layer did not remain on the glass cleaning substrate. On the other hand, in the substrate having the cleavage molecular layer, cohesive peeling occurred in the adhesive layer, and the adhesive layer was observed on both the substrate side and the polyester film layer side (Figure 9). Thus, the cleavage molecular layer of the present invention was able to enhance the adhesive strength in the adhesion between the base materials.

[0088] (Example 4-2. Measurement of Adhesive Strength of Cleavage Molecular Layer Subjected to Pyrolysis) In the cleavage substrate having the molecular layer composed of Compound 9 obtained in Example 4-1, pyrolysis of the dimerized anthracene structural part in Compound 9 was carried out. Specifically, pyrolysis of the dimerized anthracene structure was carried out by allowing a glass substrate with a polyester film attached via an adhesive layer to stand on a hot plate at 180 °C for 1 minute. Regarding the progress of the pyrolysis reaction under these conditions, it was confirmed by ultraviolet-visible absorption spectrum measurement when a cleavage substrate having a molecular layer composed of Compound 9 was heated under the same conditions that the absorption peak derived from anthracene monomer increased (Figure 10). The cleavage substrate subjected to pyrolysis was adhered to a slide glass in the same manner as in Example 4-1 to prepare a test piece for the peeling test. As a control without the cleavage molecular layer, a glass cleaning substrate was prepared by performing ultrasonic cleaning (3 hours) using a cleaning solution (Extran 2% aqueous solution) and ultrasonic cleaning in ultrapure water for 20 minutes four times, and after heat treatment under the same conditions, a peeling test was carried out.

[0089] As a result of the peeling test, the cleavage substrate having a heated cleavage molecular layer had a reduced adhesive strength compared to the unheated cleavage substrate. On the other hand, in the case of the heated substrate without a cleavage molecular layer, the adhesive strength was comparable to that in the unheated case (Figure 8). When the substrate after the peeling test was observed, peeling was observed at the interface between the glass substrate and the adhesive layer in the substrate having the heated cleavage molecular layer, and no adhesive layer remained on the substrate. In the substrate without a molecular layer, peeling was observed at the interface between the glass substrate and the adhesive layer, and the adhesive layer did not remain on the glass-washed substrate, as in the unheated case (Figure 9).

[0090] (Example 4-3. Measurement of Adhesive Strength of Cleavage Molecular Layer Subjected to Photodissociation) In the cleavage substrate having a molecular layer composed of Compound 9 obtained in Example 4-1, photodissociation of the dimerized anthracene structural portion in Compound 9 was performed. Specifically, light with a wavelength of 245 nm was irradiated onto a glass substrate to which a polyester film was attached via an adhesive layer at an intensity of 0.5 mW / cm 2 for 1 minute to perform photodissociation of the dimerized anthracene structure. When ultraviolet-visible absorption spectrum measurement was performed on the cleavage substrate having a molecular layer composed of Compound 9 when irradiated with light under the same conditions, an increase in the absorption peak derived from anthracene monomer was observed, confirming the progress of photodissociation (Figure 11). The cleavage substrate subjected to photodissociation was adhered to a slide glass in the same manner as in Example 4-1 to prepare a test piece for the peeling test. As a control without a cleavage molecular layer, a glass-washed substrate was prepared by performing ultrasonic cleaning (3 hours) using a cleaning solution (Extran 2% aqueous solution) and ultrasonic cleaning in ultrapure water for 20 minutes four times, irradiated with light under the same conditions, and then subjected to a peeling test.

[0091] As a result of the peeling test, the cleavage substrate having a cleavage molecular layer irradiated with light had a reduced adhesive strength compared to the cleavage substrate of Example 4-1. On the other hand, in the substrate without a cleavage molecular layer, the adhesive strength was comparable to that in the case of Example 4-1 (Figure 8). When the substrate after the peeling test was observed, peeling was observed at the interface between the glass substrate and the adhesive layer regardless of the presence or absence of the cleavage molecular layer, and the adhesive layer did not remain on the glass-washed substrate (Figure 9).

Claims

1. A photo- or thermo-responsive cleavage substrate having a first substrate and a cleavage molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, and forming an adhesive layer on the surface of the cleavage molecular layer, wherein the cleavage molecular layer is formed of a compound represented by any one of the following formulas (I) to (VII), the photo- or thermo-responsive cleavage substrate. 【Chemical 1】 [Chemical Formula 2] (In formulas (I) to (VII), Ra is a group represented by the following formula (A), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Ra may be the same or different. Also, adjacent Ra may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Ra is a group represented by the following formula (A), an amino group, a carboxy group, or a sulfonyl group.) 【Chemical Formula 3】 In formula (A), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-. Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. Y represents -Si(Ry1) 3 , -PO(ORy2) 2 , -OP(=O)(ORy2) 2 , -OP(=S)(ORy2) 2 , -SP(=O)(ORy2) 2 , -SP(=S)(ORy2) 2 , -NHP(=O)(Ry2) 2 , -NHP(=S)(ORy2) 2 . A plurality of Ry1 may be the same or different and represent a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group or an alkyl group. A plurality of Ry2 may be the same or different and represent a hydrogen atom, a metal atom or an alkyl group. Ara represents a (1 + na)-valent aromatic hydrocarbon group or a (1 + na)-valent heterocyclic group, Ak represents an alkylene group having 1 to 12 carbon atoms, and when there are a plurality of Ak, they may be the same or different. la represents 0 or 1, ma represents 0 or 1, and na represents an integer of 1 or more. Also, in formulas (I) to (VII), Rb is a group represented by the following formula (B), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Rb may be the same or different. Also, adjacent Rb may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Rb is a group represented by the following formula (B), an amino group, a carboxy group, or a sulfonyl group.) 【Chemical Formula 4】 In formula (B), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-, Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. When there are a plurality of Rb1, they may be the same or different and represent an alkoxysilyl group, an epoxy group, an amino group, a hydroxy group, a carbonyl group, an acrylyl group, a methacrylyl group, a vinyl group, an isocyanate group, a ureido group, a mercapto group or a halogen atom. Arb represents a (1 + nb)-valent aromatic hydrocarbon group or a (1 + nb)-valent heterocyclic group, Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. lb represents 0 or 1, mb represents 0 or 1, and nb represents an integer of 1 or more.

2. The photo- or thermo-responsive cleavage base material according to claim 1, wherein the compound is not a compound represented by the following formula (VIII), the photo- or thermo-responsive cleavage base material. [Chemical Formula 5]

3. The photo- or thermo-responsive cleavage base material according to claim 1, wherein the compound is a compound having an anthracene structure represented by the following formula (I), the photo- or thermo-responsive cleavage base material. 【Chemical Formula 6】 In formula (I), Ra is a group represented by the following formula (A), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Ra may be the same or different. Adjacent Ra may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Ra is a group represented by the following formula (A), an amino group, a carboxy group, or a sulfonyl group. 【Chemical Formula 7】 In formula (A), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-. Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. Y represents -Si(Ry1) 3 , -PO(ORy2) 2 , -OP(=O)(ORy2) 2 , -OP(=S)(ORy2) 2 , -SP(=O)(ORy2) 2 , -SP(=S)(ORy2) 2 , -NHP(=O)(Ry2) 2 , -NHP(=S)(ORy2) 2 . A plurality of Ry1 may be the same or different and represent a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group or an alkyl group. A plurality of Ry2 may be the same or different and represent a hydrogen atom, a metal atom or an alkyl group. Ara represents a (1 + na)-valent aromatic hydrocarbon group or a (1 + na)-valent heterocyclic group. Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. la represents 0 or 1, ma represents 0 or 1, and na represents an integer of 1 or more. In addition, in formula (I), Rb is a group represented by the following formula (B), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Rb may be the same or different. Adjacent Rb may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Rb is a group represented by the following formula (B), an amino group, a carboxy group, or a sulfonyl group. 【Chemical Formula 8】 In formula (B), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-, Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. When there are a plurality of Rb1, they may be the same or different and represent an alkoxysilyl group, an epoxy group, an amino group, a hydroxy group, a carbonyl group, an acrylic group, a methacrylic group, a vinyl group, an isocyanate group, a ureido group, a mercapto group or a halogen atom. Arb represents a (1 + nb)-valent aromatic hydrocarbon group or a (1 + nb)-valent heterocyclic group, Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. lb represents 0 or 1, mb represents 0 or 1, and nb represents an integer of 1 or more.)

4. A photo- or thermo-responsive cleavage substrate having a first substrate and a cleavage molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, The photo- or thermo-responsive cleavage substrate, wherein the cleavage molecular layer is formed from a compound represented by the following formula (I-a) or (I-b). 【Chemical Formula 9】 【Chemical Formula 10】

5. A photo- or thermo-responsive cleavage substrate having a first substrate, a cleavage molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, and a material layer on the cleavage molecular layer, The material layer contains at least one material selected from an adhesive, a plastic film, and a metal substrate, The photo- or thermo-responsive cleavage substrate, wherein the cleavage molecular layer is formed from a compound represented by any one of the following formulas (I) to (VII). 【Chemical Formula 1】 【Chemical 2】 In formulas (I) to (VII), Ra is a group represented by the following formula (A), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Ra's may be the same or different. Adjacent Ra's may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Ra's is a group represented by the following formula (A), an amino group, a carboxy group or a sulfonyl group. [Chemical Formula 3] In formula (A), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-. Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. Y represents -Si(Ry1) 3 , -PO(ORy2) 2 , -OP(=O)(ORy2) 2 , -OP(=S)(ORy2) 2 , -SP(=O)(ORy2) 2 , -SP(=S)(ORy2) 2 , -NHP(=O)(Ry2) 2 , -NHP(=S)(ORy2) 2 . A plurality of Ry1 may be the same or different and represent a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group or an alkyl group. A plurality of Ry2 may be the same or different and represent a hydrogen atom, a metal atom or an alkyl group. Ara represents a (1 + na)-valent aromatic hydrocarbon group or a (1 + na)-valent heterocyclic group. Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. la represents 0 or 1, ma represents 0 or 1, and na represents an integer of 1 or more. In addition, in formulas (I) to (VII), Rb is a group represented by the following formula (B), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Rb's may be the same or different. Adjacent Rb's may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Rb's is a group represented by the following formula (B), an amino group, a carboxy group or a sulfonyl group. 【Chemical Formula 4】 In formula (B), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-, Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. When there are a plurality of Rb1, they may be the same or different and represent an alkoxysilyl group, an epoxy group, an amino group, a hydroxy group, a carbonyl group, an acrylic group, a methacrylic group, a vinyl group, an isocyanate group, a ureido group, a mercapto group or a halogen atom. Arb represents a (1 + nb)-valent aromatic hydrocarbon group or a (1 + nb)-valent heterocyclic group, Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. lb represents 0 or 1, mb represents 0 or 1, and nb represents an integer of 1 or more.

6. A photo- or thermo-responsive cleavage substrate having a first substrate, a cleavage molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, a material layer on the cleavage molecular layer, and a second substrate on the material layer, wherein the material layer is an adhesive layer containing an adhesive, and the cleavage molecular layer is formed from a compound represented by any of the following formulas (I) to (VII), a photo- or thermo-responsive cleavage substrate. 【Chemical 1】 【Chemical Formula 2】 In formulas (I) to (VII), Ra is a group represented by the following formula (A), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group, or an acrylate group. A plurality of Ra may be the same or different. Also, adjacent Ra may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocyclic ring, and these rings may have substituents. However, at least one of Ra is a group represented by the following formula (A), an amino group, a carboxy group, or a sulfonyl group. 【Chemical Formula 3】 In formula (A), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-. Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. Y represents -Si(Ry1) 3 , -PO(ORy2) 2 , -OP(=O)(ORy2) 2 , -OP(=S)(ORy2) 2 , -SP(=O)(ORy2) 2 , -SP(=S)(ORy2) 2 , -NHP(=O)(Ry2) 2 , -NHP(=S)(ORy2) 2 . A plurality of Ry1 may be the same or different and represent a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group or an alkyl group. A plurality of Ry2 may be the same or different and represent a hydrogen atom, a metal atom or an alkyl group. Ara represents a (1 + na)-valent aromatic hydrocarbon group or a (1 + na)-valent heterocyclic group. Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. la represents 0 or 1, ma represents 0 or 1, and na represents an integer of 1 or more. In formulas (I) to (VII), Rb is a group represented by the following formula (B), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group, or an acrylate group. A plurality of Rb may be the same or different. Also, adjacent Rb may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocyclic ring, and these rings may have substituents. However, at least one of Rb is a group represented by the following formula (B), an amino group, a carboxy group, or a sulfonyl group. 【Chemical Formula 4】 In formula (B), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-, Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. When there are a plurality of Rb1, they may be the same or different and represent an alkoxysilyl group, an epoxy group, an amino group, a hydroxy group, a carbonyl group, an acrylic group, a methacrylic group, a vinyl group, an isocyanate group, a ureido group, a mercapto group or a halogen atom. Arb represents a (1 + nb)-valent aromatic hydrocarbon group or a (1 + nb)-valent heterocyclic group, Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. lb represents 0 or 1, mb represents 0 or 1, and nb represents an integer of 1 or more.

7. A photo- or thermo-responsive cleavage substrate having a first substrate and a cleavage molecular layer capable of reversible cleavage and adhesion by light or heat on the surface of the first substrate, The photo- or thermo-responsive cleavage substrate, wherein the cleavage molecular layer is formed from a compound represented by any one of the following formulas (I) to (VII). 【Chemical 1】 [Chemical 2] In formulas (I) to (VII), Ra is a group represented by the following formula (A), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group, or an acrylate group. A plurality of Ra may be the same or different. Also, adjacent Ra may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocyclic ring, and these rings may have substituents. However, at least one of Ra is a group represented by the following formula (A). [Chemical Formula 3] In formula (A), Z represents -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S-, or -Ak-. Rz represents a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group, or an acrylate group. When there are a plurality of Rz, they may be the same or different. Y represents -Si(Ry1)3. A plurality of Ry1 may be the same or different and represent an alkoxy group. Ara represents a (1 + na)-valent aromatic hydrocarbon group or a (1 + na)-valent heterocyclic group. Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. la represents 0 or 1, ma represents 0 or 1, and na represents an integer of 1 or more. In formulas (I) to (VII), Rb is a group represented by the following formula (B), or a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an acyl group, an acyloxy group, an amide group, a carboxy group, a sulfonyl group, an alkenyl group, an alkynyl group or an acrylate group. A plurality of Rb may be the same or different. Adjacent Rb may be linked to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring, and these rings may have substituents. However, at least one of Rb is a group represented by the following formula (B). 【Chemical Formula 4】 In formula (B), Z is -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)-, -N(Rz)-, -C(=O)N(Rz)-, -N(Rz)C(=O)-, -N(Rz)C(=O)N(Rz)-, -Ak-C(=O)O, -Ak-N(Rz)-, -Ak-C(=O)N(Rz)-, -Ak-N(Rz)C(=O)-, -Ak-N(Rz)C(=O)N(Rz)-, -O-, -S- or -Ak-, Rz is a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a monovalent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxy group, a hydroxy group, an alkenyl group, an alkynyl group or an acrylate group. When there are a plurality of Rz, they may be the same or different. Rb1 represents an alkoxysilyl group. Arb represents a (1 + nb)-valent aromatic hydrocarbon group or a (1 + nb)-valent heterocyclic group, Ak represents an alkylene group having 1 to 12 carbon atoms. When there are a plurality of Ak, they may be the same or different. lb represents 0 or 1, mb represents 0 or 1, and nb represents an integer of 1 or more. The group represented by the following (AA) in formula (A) and the group represented by the following (BB) in formula (B) are the same. [Chemical 3-2] 【Chemical Formula 4-2】 ）

8. A method for cleaving the cleavage molecular layer in the photo- or thermo-responsive cleavage base material according to claims 1 to 7, comprising the step of applying light or heat to the cleavage molecular layer.

9. A method for adhering the cleavage molecular layer cleaved by the method according to claim 8, A method comprising the step of applying light to the cracked cracked molecular layer.

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