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WO2008152743A1 - Procédé de liaison, puce biochimique et pièce optique obtenues par le procédé - Google Patents

Procédé de liaison, puce biochimique et pièce optique obtenues par le procédé Download PDF

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Publication number
WO2008152743A1
WO2008152743A1 PCT/JP2007/062545 JP2007062545W WO2008152743A1 WO 2008152743 A1 WO2008152743 A1 WO 2008152743A1 JP 2007062545 W JP2007062545 W JP 2007062545W WO 2008152743 A1 WO2008152743 A1 WO 2008152743A1
Authority
WO
WIPO (PCT)
Prior art keywords
covalently bonded
group
members
biochemical chip
organic film
Prior art date
Application number
PCT/JP2007/062545
Other languages
English (en)
Inventor
Kazufumi Ogawa
Original Assignee
Kazufumi Ogawa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kazufumi Ogawa filed Critical Kazufumi Ogawa
Priority to PCT/JP2007/062545 priority Critical patent/WO2008152743A1/fr
Publication of WO2008152743A1 publication Critical patent/WO2008152743A1/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00Additional features of adhesives in the form of films or foils
    • C09J2301/40Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to a bonding method of two members, and a biochemical chip and an optical part, which are produced using the bonding method.
  • the present invention relates to a biochemical chip produced by facing and bonding a pair of biochemical chip substrates processed to have a fine flow path or hole on the surface thereof, and a production method thereof, where the biochemical substrates are bonded without damaging the flow path or hole.
  • the biochemical chip includes a chemical chip, a biochip, a biochemical electrophoresis chip, a biochemical reactor, a biochemical fluidic system, a DAN chip and the like, which are used for a chemical experiment, a bio-experiment, medical diagnosis and the like.
  • the present invention relates to an optical part produced by facing and bonding a pair of optical members having flatness on the surface and optical characteristics on the bonding face, and a production method thereof, where the optical members are bonded without damaging the flatness and optical characteristics.
  • the optical part includes a lens, a prism, an optical fiber, an optical recording medium and the like.
  • An objective of the present invention is to provide a bonding method of a pair of biochemical chip substrates of which at least one is processed to have a fine hole and groove in a micron level, without damaging the fine hole and groove, that is, without covering those and having gaps, and to provide a biochemical chip without a defect produced using the bonding method with low cost.
  • a bonding method comprising: a step for producing a first and second members in which a organic thin film having a photo-reactive functional group is pre-formed; and a step for bonding the first and second members through the organic thin films by irradiating light while contacting the first and second members.
  • a 2nd invention is the bonding method in the 1st invention, in which at least the photo-reactive functional group is a chalconyl group or a diacetylene group.
  • a 3rd invention is the bonding method in the 2nd invention, the method comprising, a step for contacting and reacting a member with a chemisorption liquid produced by mixing a chlorosilane compound, which contains the chalconyl group or the diacetylene group as the photo-reactive functional group, and a non-aqueous organic solvent; and producing the first and second members having an organic thin film or a chemisorption monomolecular film which contains the chalconyl group or the diacetylene group, or a step for contacting and reacting a member with a chemisorption liquid produced by mixing an alkoxysilane compound containing the chalconyl group or the diacetylene group, a silanol condensing catalyst, and a non-aqueous organic solvent; and producing the first and second members having an organic thin film or a chemisorption monomolecular film which contains the chalconyl group or the diacetylene group.
  • a 4th invention is the bonding method in the 1st invention, in which at least one of the contacting end faces of the first and second members and the first and second members has transparency with respect to light, and the light is irradiated from the transparent member side so as to bond the first and second members.
  • a 5th invention is a biochemical chip, in which a first biochemical chip substrate and a second biochemical chip substrate are bonded by a covalent bond through at least an organic film covalently bonded to the surface of the first biochemical chip substrate and an organic film covalently bonded to the surface of the second biochemical chip substrate.
  • a 6th invention is the biochemical chip in the 5th invention, in which at least the organic film covalently bonded to the surface of the first biochemical chip substrate and the organic film covalently bonded to the surface of the second biochemical chip substrate contain the same photo-reactive functional group.
  • a 7th invention is the biochemical chip in the 5th invention, in which at least the organic film covalently bonded to the surface of the first biochemical chip substrate and the organic film covalently bonded to the surface of the second biochemical chip substrate are a monomolecular film respectively.
  • a 8th invention is an optical part, in which a first optical member and a second optical member are bonded by a covalent bond through at least an organic film covalently bonded to the surface of the first optical member and an organic film covalently bonded to the surface of the second optical member.
  • a 9th invention is the optical part in the 8th invention, in which at least the organic film covalently bonded to the surface of the first optical member and the organic film covalently bonded to the surface of the second optical member contain the same photo-reactive functional group.
  • a 10th invention is the optical part in the 8th invention, in which at least the organic film covalently bonded to the surface of the first optical member and the organic film covalently bonded to the surface of the second optical member are a monomolecular film respectively.
  • An objective of the present invention is to provide a biochemical chip produced by a step for producing a first and second members in which a organic thin film having a photo-reactive functional group is pre-formed; and a step for bonding the first and second members through the organic thin films by irradiating light while contacting the first and second members.
  • the biochemical chip has a first biochemical chip substrate and a second biochemical chip substrate, which are covalently bonded through an organic film covalently bonded to the surface of the first biochemical chip substrate and an organic film covalently bonded to the surface of the second biochemical chip substrate.
  • an objective of the present invention is to provide an optical part having a first optical part and a second optical part, which are bonded by a covalent bond through an organic film covalently bonded to the surface of the first optical part and an organic film covalently bonded to the surface of the second optical part.
  • the photo-reactive functional group is a chalconyl group or a diacetylene group
  • the covalent bond is generated by a photo-addition reaction, so that it is preferable to obtain adhesive strength.
  • the first and second members are produced by contacting and reacting a member with a chemisorption liquid produced by mixing a chlorosilane compound, which contains the chalconyl group or the diacetylene group as the photo-reactive functional group, and a non-aqueous organic solvent, so as to have an organic thin film or a chemisorption monomolecular film which contains the chalconyl group or the diacetylene group.
  • the first and second members are produced by contacting and reacting a member with the chemisorption liquid produced by mixing an alkoxysilane compound containing the chalconyl group or the diacetylene group, a silanol condensing catalyst, and a non-aqueous organic solvent, so as to have the organic thin film or the chemisorption monomolecular film which contains the chalconyl group or the diacetylene group.
  • the chalconyl group or the diacetylene group is exposed to the member surfaces, so that it is preferable to bond the members.
  • At least one of the contacting end faces of the first and second members and the first and second members has transparency with respect to light, and the light is irradiated from the transparent member side so as to bond the first and second members.
  • a matching deviation between the members can be decreased, so that it is preferable to increase accuracy.
  • the biochemical chip and the optical part can be produced by bonding the both members with the covalent bond through the each organic film.
  • the organic film covalently bonded to the surface of the first optical member and the organic film covalently bonded to the surface of the second optical member are monomolecular films respectively, the uniform bonding face can be obtained, so that it is preferable to bond the biochemical chip or the optical part.
  • the present invention has an effect to bond a pair of biochemical chip substrates of which at least one is processed to have a fine hole and groove in a micron level without damaging the fine hole and groove, that is, without covering those by adhesive, and without having gaps, and to provide a biochemical chip without a defect with the high yield. Further, there is the effect to bond without damaging optical characteristics on the bonding face, and to provide an optical part having high characteristics with the high yield.
  • FIG.1 is a schematic view for explaining a process for bonding a pair of glass biochemical chip substrates in Example 1 of the present invention, where the process is expanded to the molecular level
  • 1A is a view of the surface of a first glass substrate before the reaction
  • 1 B is a view after forming a monomolecular film containing a chalconyl group
  • 1C is a cross sectional view in which the first and second glass substrates are bonded.
  • the present invention is to produce and provide a biochemical chip and an optical member by a step for producing a first and second members in which a monomolecular film-shaped organic thin film having a photo-reactive functional group is pre-formed; and a step for bonding the first and second members through the organic thin films by irradiating light while contacting the first and second members. Therefore, by using the method of the present invention, a pair of biochemical chip substrates of which at least one is processed to have a fine hole and groove in a micron level can be bonded without damaging the fine hole and groove, that is, without covering those, and without having gaps, and a biochemical chip without a defect can be provided with low cost. Further, the optical part can be bonded to have uniform thickness without damaging optical characteristics on the bonding face, and the optical part having high characteristics can be provided with low cost.
  • the biochemical chip according to the present invention includes a chemical chip, a biochemical electrophoresis chip, a biochemical reactor, a biochemical fluidic system, a DAN chip and the like, which are used for a chemical experiment, a bio-experiment, medical diagnosis and the like.
  • the optical part includes a lens, a prism, an optical fiber, an optical recording medium and the like.
  • the present invention will be described using a chemical chip and a lens as representative examples. [Example 1]
  • a pair of processed glass biochemical chip substrates 1 used for a chemical chip was prepared, well washed and dried (a plastic substrate such as an acrylic resin or the like might be used, and when the plastic substrate was used, it could be used like the glass substrate by thinly oxidizing the surface by corona treatment, excimer treatment, plasma treatment or the like so as to have hydrophilicity).
  • a plastic substrate such as an acrylic resin or the like might be used, and when the plastic substrate was used, it could be used like the glass substrate by thinly oxidizing the surface by corona treatment, excimer treatment, plasma treatment or the like so as to have hydrophilicity).
  • the chemisorption liquid (it is said to as the adsorbent solution) was prepared by solving a chemical adsorbent, which includes a photo-reactive functional group to a functional part, in a non-aqueous solvent (for example, dehydrated nonane) at the concentration of about 0.1 w.t.%, where the photo-reactive functional group was the chemicals including, for example, a chalconyl group ((C 5 H 5 )CO(CH) 2 (C 5 H 5 )-) at one end and an chlorosilyl group (an active portion) at another end, that is, for example, (C 6 H 5 )(CH)2CO(C 6 H4)O(CH 2 )6OSiCl3.
  • a chemical adsorbent which includes a photo-reactive functional group to a functional part
  • a non-aqueous solvent for example, dehydrated nonane
  • the photo-reactive functional group was the chemicals including, for example, a chalconyl group ((C
  • the chip substrate was dipped in the adsorbent solution in a dry atmosphere (a relative humidity was preferably 30% or less), and stirred and reacted.
  • a relative humidity was preferably 30% or less
  • V the chlorosilyl group (SiCI) of the chemical adsorbent was reacted with the hydroxyl groups (OH) of the chip substrates, and thereby, dehydrochlorinatin reaction occurred so as to form a bond shown in the following chemical formula (1) on the whole surface of the chip substrate.
  • a chip substrate covered with a monomolecular film 3, 3' including the chemical adsorbent was obtained.
  • the thickness of the glass was not changed, and the flow path and hole which were pre-processed were not damaged.
  • the chalconyl group in the monomolecular film on the surface of the chip substrate has photo-reactivity within the range of 250 to 400 nm.
  • the oppositely contacted chalconyl groups shown in the following chemical formula (2) were added, so as to obtain a biochemical chip 5 in which two glass biochemical chip substrates were bonded through the covalent bond between the two monomolecular films (FIG.1C).
  • a bond 4 was generated by an addition-reaction of the chalconyl groups.
  • the substrate was opaque, the light might be irradiated from the end face.
  • a pair of processed glass biochemical chip substrates 1 used for a chemical chip was prepared, well washed and dried (a plastic substrate such as an acrylic resin or the like might be used, and when the plastic substrate was used, it could be used like the glass substrate by thinly oxidizing the surface by corona treatment, excimer treatment, plasma treatment or the like so as to have hydrophilicity), like Example 1.
  • a plastic substrate such as an acrylic resin or the like might be used, and when the plastic substrate was used, it could be used like the glass substrate by thinly oxidizing the surface by corona treatment, excimer treatment, plasma treatment or the like so as to have hydrophilicity
  • the chemisorption liquid was prepared by the steps of: weighing 99 wt.% of chemicals including a photo-reactive functional group to a functional part as a chemical adsorbent, where the reactive functional group was the chemicals including, for example, the diacetylene group at one end and an alkoxysilyl group at another end, that is, for example, the chemicals shown in the following formula (3); weighing 1 wt.% of dibutyl-tin-acetylacetonate as the silanol condensing catalyst; and solving the above-described weighed chemical materials in a silicone solvent, for example, a hexamethyldisiloxane solvent so as to have the total concentration of about 1 wt.% (the concentration of the chemical adsorbent was preferably about 0.5 to 3%).
  • a silicone solvent for example, a hexamethyldisiloxane solvent
  • the chemisorption liquid was coated on the surfaces of the glass substrates, and reacted at a normal atmosphere (a relative humidity was 45%) for 2 hours.
  • a -Si(OCH 3 ) group of the chemical adsrobent and the hydroxyl groups were dealcoholation-reacted (in this case, deCH 3 OH-reacted) under the existence of the silanol condensing catalyst, so as to from a bond shown in the following formula (4), like Example 1.
  • a chemisorption monomolecular film containing the diacetylene group was formed to have the film thickness of about 1 nm, where the film 3 was chemically bonded to the whole surfaces of the glass substrates.
  • the film thickness was only the length of 1 molecule (about 1 nm), the thickness of the glass was not changed, and the flow path and hole which were pre-processed were not damaged.
  • the solvent was vaporized and the chemical adsorbent remained on the surface of the glass substrate was reacted with moisture in the atmosphere, so as to form a remarkable-thin organic film (the polymer film in this case) including the chemical adsorbent on the surface thereof.
  • the film thickness was thick a little, reactivity at the time of bonding was hardly changed.
  • the chip substrate has photo-reactivity within the range of 30 to 400 nm.
  • the chip substrate faced to be pressed and contacted with a substrate which was similarly processed, and ultraviolet radiation was irradiated from the glass substrate side, and thereby, the oppositely contacted diacetylene group shown in the following chemical formula (5) were added, so as to obtain a biochemical chip in which two glass biochemical chip substrates were bonded through the covalent bond between the two monomolecular films.
  • the total thickness of the film of the formed bonding layer was about 1 nm, so that transparency on the bonding face was not damaged at all. Further, the bonding thickness was remarkably thinner than the wavelength of visible light, there were no loss of the light on the bonding interface.
  • (C 6 H 5 ) CO(CH) 2 (C 6 H 4 ) shows the chalconyl group.
  • a metal carboxylate, a metal carboxylate ester, a metal carboxylate polymer, a metal carboxylate chelate, a titanic acid ester, a titanic acid ester chelate and the like can be used as the silanol condensing catalyst.
  • stannous acetic acid dibutyltin dilaurate, dibutyltin dioctanoate, dibutyltin diacetate, dioctyltin dilaurate, dioctyltin dioctanoate, dioctyltin diacetate, stannous dioctanate, lead naphthenate, cobalt naphthenate, 2-iron ethylhexenoate, a dioctyltin bisoctylthioglycolate ester, a dioctyltin maleate ester, a dibutyltin maleate polymer, a dimethyltin mercapto propionate polymer, dibutyltin bisacetyl acetate, dioctyltin bisacetyl laurate, tetrabutyl titanate, tetranony
  • a solvent of the film forming solution an organic chlorine-based solvent not including aqueous, a hydrocarbon-based solvent, a carbon fluoride-based solvent, or a silicone-based solvent can be used.
  • a boiling point of the solvent is about 50°to 250 0 C.
  • non-aqueous petroleum naphtha, solvent naphtha, petroleum ether, petroleum benzine, isoparaffin, normalparaffin, decalin, industrial gasoline, nonane, deccan, kerosene, dimethylsilicone, phenylsilicone, alkyl-modified silicone, polyether silicone, and the like can be used.
  • an alcohol-based solvent such as methanol, ethanol or the like, or dimethylformamide can be used in addition to the above-described solvents.
  • a carbon fluoride based solvent a chlorofluocarbon-based solvent
  • Fluorinate produced by 3M Corporation
  • Afroude produced by Asahi Aluminum Corporation
  • these solvent can be used independently or used by mixing two or more kinds if those enable to be mixed.
  • the organic chlorine-based solvent such as chloroform can be added.
  • silanol condensing solvent instead of the above-described silanol condensing solvent, when the ketimine compound, an organic acid, the aldimine compound, the enamine compound, the oxazolidine compound, the aminoalkylalkoxy silane compound were used, the processing time could be shortened to about 1/2 to 2/3 although having the same concentration.
  • the silanol condensing catalyst when used by mixing with the ketimine compound, the organic acid, the aldimine compound, the enamine compound, the oxazolidine compound, or the aminoalkylalkoxy silane compound (although the mixing rate could be within the range of 1 :9 to 9:1 , the range of about 1 :1 was ordinary preferable), the processing time could be shortened more several times, and the time for forming the film could be shortened to one / several.
  • the ketimine compound, the organic acid, the aldimine compound, the enamine compound, the oxazolidine compound, and the aminoalkylalkoxy silane compound had higher activity than the silanol condensing catalyst.
  • the silanol condensing catalyst was used by mixing with one of the ketimine compound, the organic acid, the aldimine compound, the enamine compound, the oxazolidine compound, and the aminoalkylalkoxy silane compound, the reactivity became further higher.
  • the ketimine compound used in the present invention was not limited especially.
  • the followings could be used, that is, 2,5,8- triaza-1 ,8-nonadien, 3, 1 i-dimethyl-4,7, 10-triaza-3, 10-tridecadien, 2,10-dimethyl-3,6,9-triaza-2,9-undecadien,
  • organic acid used in the present invention was not limited especially.
  • formic acid, acetic acid, propionic acid, butyric acid, malonic acid or the like could be used, and approximately similar results could be obtained.

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Abstract

La présente invention porte sur une puce biochimique munie d'un premier substrat de puce biochimique et d'un second substrat de puce biochimique. Les deux substrats sont liés par une liaison covalente par l'intermédiaire d'un film organique lié de façon covalente à la surface du premier substrat de puce biochimique et d'un film organique lié de façon covalente à la surface du second substrat de puce biochimique. L'invention porte également sur une pièce optique munie d'un premier élément optique et d'un second élément optique lies par une liaison covalente par l'intermédiaire d'un film organique lié de façon covalente à la surface du premier élément optique et d'un film organique lié de façon covalente à la surface du second élément optique.
PCT/JP2007/062545 2007-06-15 2007-06-15 Procédé de liaison, puce biochimique et pièce optique obtenues par le procédé WO2008152743A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/JP2007/062545 WO2008152743A1 (fr) 2007-06-15 2007-06-15 Procédé de liaison, puce biochimique et pièce optique obtenues par le procédé

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PCT/JP2007/062545 WO2008152743A1 (fr) 2007-06-15 2007-06-15 Procédé de liaison, puce biochimique et pièce optique obtenues par le procédé

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WO2008152743A1 true WO2008152743A1 (fr) 2008-12-18

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112687605A (zh) * 2020-12-28 2021-04-20 华东师范大学 一种减少芯片电子辐射损伤的方法和受电子辐射损伤较小的芯片

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0425142A (ja) * 1990-05-21 1992-01-28 Matsushita Electric Ind Co Ltd 半導体素子の実装方法
JPH076938A (ja) * 1993-04-23 1995-01-10 Canon Inc 固相接合法
JPH10325956A (ja) * 1997-05-26 1998-12-08 Matsushita Electric Ind Co Ltd 液晶配向膜とその製造方法およびその配向膜を用いた液晶表示装置
JP2001138434A (ja) * 1998-09-16 2001-05-22 Matsushita Electric Ind Co Ltd 機能性膜及びその製造方法、並びにそれを用いた液晶表示素子及びその製造方法
JP2003246971A (ja) * 2002-02-25 2003-09-05 Kansai Tlo Kk 箔状ないし膜状物体の接着方法及びその方法によって得られた衝撃波速度計測用ターゲット
WO2004043853A1 (fr) * 2002-11-13 2004-05-27 Nippon Soda Co., Ltd. Dispersoïde à liaison métal-oxygène, film d'oxyde métallique et film monomoléculaire
JP2007033167A (ja) * 2005-07-26 2007-02-08 Kagawa Univ バイオケミカルチップとその製造方法
JP2007161913A (ja) * 2005-12-15 2007-06-28 Kagawa Univ 接着方法とそれを用いたバイオケミカルチップと光学部品

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0425142A (ja) * 1990-05-21 1992-01-28 Matsushita Electric Ind Co Ltd 半導体素子の実装方法
JPH076938A (ja) * 1993-04-23 1995-01-10 Canon Inc 固相接合法
JPH10325956A (ja) * 1997-05-26 1998-12-08 Matsushita Electric Ind Co Ltd 液晶配向膜とその製造方法およびその配向膜を用いた液晶表示装置
JP2001138434A (ja) * 1998-09-16 2001-05-22 Matsushita Electric Ind Co Ltd 機能性膜及びその製造方法、並びにそれを用いた液晶表示素子及びその製造方法
JP2003246971A (ja) * 2002-02-25 2003-09-05 Kansai Tlo Kk 箔状ないし膜状物体の接着方法及びその方法によって得られた衝撃波速度計測用ターゲット
WO2004043853A1 (fr) * 2002-11-13 2004-05-27 Nippon Soda Co., Ltd. Dispersoïde à liaison métal-oxygène, film d'oxyde métallique et film monomoléculaire
JP2007033167A (ja) * 2005-07-26 2007-02-08 Kagawa Univ バイオケミカルチップとその製造方法
JP2007161913A (ja) * 2005-12-15 2007-06-28 Kagawa Univ 接着方法とそれを用いたバイオケミカルチップと光学部品

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112687605A (zh) * 2020-12-28 2021-04-20 华东师范大学 一种减少芯片电子辐射损伤的方法和受电子辐射损伤较小的芯片
CN112687605B (zh) * 2020-12-28 2022-07-29 华东师范大学 一种减少电子辐射损伤的方法和芯片

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