WO2004017071A2 - Procede pour relier des surfaces, semi-conducteur a surfaces reliees, biopuce et biocapteur - Google Patents

Procede pour relier des surfaces, semi-conducteur a surfaces reliees, biopuce et biocapteur Download PDF

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Publication number
WO2004017071A2
WO2004017071A2 PCT/EP2003/008955 EP0308955W WO2004017071A2 WO 2004017071 A2 WO2004017071 A2 WO 2004017071A2 EP 0308955 W EP0308955 W EP 0308955W WO 2004017071 A2 WO2004017071 A2 WO 2004017071A2
Authority
WO
WIPO (PCT)
Prior art keywords
monoreactive
substance
reactive
carrier
semiconductor
Prior art date
Application number
PCT/EP2003/008955
Other languages
German (de)
English (en)
Other versions
WO2004017071A3 (fr
Inventor
Holger Klapproth
Original Assignee
Micronas Holding Gmbh
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 Micronas Holding Gmbh filed Critical Micronas Holding Gmbh
Priority to AU2003266280A priority Critical patent/AU2003266280A1/en
Publication of WO2004017071A2 publication Critical patent/WO2004017071A2/fr
Publication of WO2004017071A3 publication Critical patent/WO2004017071A3/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/04—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving separate application of adhesive ingredients to the different surfaces to be joined
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
    • H01L24/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L25/00—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
    • H01L25/50—Multistep manufacturing processes of assemblies consisting of devices, each device being of a type provided for in group H01L27/00 or H01L29/00
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
    • H01L2224/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/701—Organic molecular electronic devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/761—Biomolecules or bio-macromolecules, e.g. proteins, chlorophyl, lipids or enzymes

Definitions

  • the present invention relates to a method for connecting surfaces, a semiconductor whose surfaces are connected to the surface of a second semiconductor and a bio-chip or bio-sensor comprising such a semiconductor.
  • biochips For the qualitative and quantitative detection of substances in a sample to be analyzed, planar systems are used, which are referred to as biochips or biosensors.
  • the biochips form a carrier, on the surface of which a large number of grid-like detection areas are formed. The individual areas differ from each other in their specificity towards a substance to be detected. Since biological systems in particular are based on interactions of biologically active macromolecules, biochips are particularly suitable for the detection of biologically active molecules such as nucleic acids (DNA or RNA), oligo- and polypeptides, proteins, antibodies as well as receptors and ligands.
  • DNA or RNA nucleic acids
  • oligo- and polypeptides proteins
  • antibodies as well as receptors and ligands.
  • biochips were produced that are based on solid-phase technologies with self-organizing monolayers ("seif-assembled monolayers", "SAM”) of bifunctional molecules.
  • SAM self-organizing monolayers
  • the bifunctional molecules bind on one side to the surface of the solid support and on the other side to macromolecules that are present in a sample to be examined. A certain interaction is detected with the aid of suitable labels, for example radioactive labeling or chemo- or bioluminescence.
  • suitable labels for example radioactive labeling or chemo- or bioluminescence.
  • surfaces made of metal or semimetal oxides, such as aluminum oxide, quartz glass or glass are immersed in a solution of bifunctional molecules ("liner").
  • the solution contains a halosilane or alkoxysilane group for coupling to the support surface, so that a self-organizing monolayer can form.
  • the linkers are coupled to the macromolecules to be detected from the sample to be tested via suitable further functional groups, such as amino or epoxy groups.
  • WO 02/10752 A2 describes a sensor chip with a carrier surface made of metal oxide or semimetal oxide, to which a homogeneous polysiloxane layer is applied.
  • the sensor chip is immersed in a solution of a bifunctional silane and pulled out at a defined speed in the range from 0.1 to 10 mm / s.
  • the bifunctional silane is present in a solvent with a boiling temperature between 50 and 150 ° C, a concentration of 0.1 to 50% by weight and a temperature of 20 to 100 ° C.
  • the layer of bifunctional silane is formed by crosslinking, forming a polysiloxane multilayer on the surface of the sensor chip.
  • WO 00/43539 A2 describes a layer ("monolayer") which is composed of a polyfunctional polymer.
  • Polymer chains are arranged on a surface and each polymer chain comprises many identical or different units, which in turn carry functional groups. An interaction between the polymer and a molecule from a sample to be tested is possible via these functional groups.
  • the polyfunctional polymer chains are also called “polymer brush” because they protrude from the surface like brushes.
  • the present invention relates to a method for connecting surfaces, which can also be referred to as molecular bonding of surfaces. The process therefore provides a new connection technology for two surfaces. For this purpose, the surface of a first carrier is coated with at least one monoreactive substance.
  • the monoreactive substance is then immobilized on the surface of the first support and thus permanently attached.
  • the first coated carrier produced in this way is brought into spatial proximity with a second carrier coated with a monoreactive substance, so that the coated surfaces face one another.
  • the contact between the two coated surfaces causes the monoreactive substances to react chemically with one another so that a permanent, permanent connection is created.
  • the surfaces of the two supports can be coated simultaneously with the same reactive substance.
  • different reactive substances can be used to coat the two surfaces of the first and the second carrier.
  • polymers with identical monomers form after the chemical bond, while when different reactive substances are used, polymers form from different monomers.
  • both the first and the second carrier can be coated not only with one but also with two or more identical or different reactive substances. In this way, any polymers can be assembled from a wide variety of monomer units.
  • a substance for crosslinking can additionally be applied to one or both coated supports.
  • This cross-linking substance is a bireactive molecule, a polymer brush (WO 00/43539 A2), a so-called “surface attached network” (EP 0 210 578) or a coating made of a thin polymer film.
  • the surfaces of the first and second carriers can be coated with an epoxy, so that crosslinking by means of polyethylglycol is possible.
  • an epoxy is shown by way of example in FIG. 3.
  • the carrier used in the process is a semiconductor or a related substance.
  • the surface of the semiconductor consists of silicon, semimetal oxides, especially silicon oxide (SiO x ), aluminum oxide or silicon nitride.
  • the monoreactive substance can be applied to the surface of the semiconductor in one layer in the form of a monolayer.
  • FIG. 4 shows an example of a monolayer of an aminosilane.
  • the reactive substance can also be applied to the surface in several layers as reactive layers. These reactive layers are collectively referred to as a poly layer, which forms a gel-like structure.
  • the gel structure has the particular advantage that unevenness in the surface structure can be effectively compensated for.
  • a layer thickness of the monoreactive substance of approximately 2 nm is particularly suitable.
  • the monoreactive substance can in particular be a reactive silane.
  • Silane has only one silane group as a reactive group.
  • the organic group is then, for example, a saturated aliphatic hydrocarbon.
  • a chemical link to these groups can be established by means of radical formers, but the silane itself is not reactive.
  • the compound is extremely stable since it has no other reactive groups. The binding to a reactive substance leads to a reaction product that is final, so that the binding cannot be broken apart from extreme violence.
  • silanes are chlorosilanes and alkoxysilanes, although thiols or disulfide groups can also be used.
  • the following substances are particularly suitable as starting silanes, the structural formulas of which are given in FIG. 1:
  • 4,4'-azobis (4-cyano-petanoic acid (3'-chlorodimethylsilyl) propyl ester); represented as compound 1 in FIG. 1, the corresponding di- and trichloro or mono-, di- and trialkoxysilane analogs are also suitable;
  • glycidoxypropyltrimethoxysilane for coating the surface of the first support and aminopropyltrimethoxysilane for coating the surface of the second support is particularly preferred. If an azosilane is used to coat the first support and a propyl-trichlorosilane is used to coat the second support, the chemical connection between the two silanes can take place via thermally induced radical formation.
  • the monoreactive substances can be applied by various processes such as spin coating, gas phase deposition, condensation or spraying.
  • immersing the substrates to be coated in liquids with reactive substance is particularly suitable. This coating is referred to as dip coating.
  • the chemical bond that occurs between the monoreactive substances on the surfaces of the two supports is a covalent bond. Examples of such connections are shown in FIGS. 2, 3 and 5, the two supports, which are provided with the reference numerals 1 and 2, also being shown schematically in FIG. 5.
  • the type of molecular bond on which the covalent bond between the monoreactive substances is based is a nucleophilic or electrophilic addition or substitution.
  • the functional groups are selected from the prior art literature taking into account the class of molecules to be immobilized. The conditions of the reaction time, the temperature and the pH value are also decisive for the selection. A number of examples can be found in the publication by GT Hermanson, "Bioconjugate Techniques", Academic Press 1996.
  • Active or reactive esters such as N-hydroxysuccinimides (NHS esters) and amines, aliphatics, epoxies, thiols, isothiocyanates, isocyanates, azides, carboxyl groups or maleimides are particularly suitable.
  • spacers can be arranged between the functional groups mentioned above and the actual silane.
  • spacers in particular acrylic and methacrylic esters or amides of C 2 0 -C ⁇ Alkohohlen or C2 - Cio amines in question.
  • the alcohols or amines carry additional functional groups at the end that does not form the ester or amide bond. This functional group is either required directly for the interaction with the other reactive silane, or it is formed in a further step by the action of another functional group.
  • the spacers can also be formed from individual monomers such as, for example, acrylic chlorides or methacrylic acid and their derivatives or reactive esters such as N-hydroxysuccinimides or other monomers, for example maleic anhydride.
  • the preferred reactive monomers can form covalent bonds with the bifunctional alcohols or amines used as spacers.
  • the monoreactive substance can form a cross-linked polymer with reactive side groups on the surface of the support. This creates a particularly strong connection between the two semiconductors.
  • the polymer preferably has a melting point of below 150 ° C., so that the polymer can be converted into the liquid state when the semiconductors are connected.
  • a spacer with a photolabile group is activated by exposure, so that the reactive group from the Si long group is separated. This prevents a connection at this point.
  • any sil system can be destroyed by using hard UV light, so that the specific reactivity no longer exists at this point.
  • the invention also relates to a semiconductor, the surface of which is connected to the surface of a second semiconductor by the method described, and a biochip or biosensor which has such a semiconductor.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Mathematical Physics (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Theoretical Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Pressure Sensors (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

Abstract

L'invention concerne un procédé pour coller des surfaces ainsi que des semi-conducteurs présentant des surfaces ainsi reliées. L'invention concerne également des biopuces et des biocapteurs comprenant ledit semi-conducteur.
PCT/EP2003/008955 2002-08-14 2003-08-12 Procede pour relier des surfaces, semi-conducteur a surfaces reliees, biopuce et biocapteur WO2004017071A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003266280A AU2003266280A1 (en) 2002-08-14 2003-08-12 Method for joining surfaces, semiconductor with joined surfaces, bio-chip and bio-sensor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10237280A DE10237280A1 (de) 2002-08-14 2002-08-14 Verfahren zum Verbinden von Oberflächen, Halbleiter mit verbundenen Oberflächen sowie Bio-Chip und Bio-Sensor
DE10237280.2 2002-08-14

Publications (2)

Publication Number Publication Date
WO2004017071A2 true WO2004017071A2 (fr) 2004-02-26
WO2004017071A3 WO2004017071A3 (fr) 2004-05-27

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AU (1) AU2003266280A1 (fr)
DE (1) DE10237280A1 (fr)
WO (1) WO2004017071A2 (fr)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2008032128A1 (fr) * 2006-09-15 2008-03-20 National Center Of Scientific Research ''demokritos'' Technique d'assemblage

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FR2887244A1 (fr) * 2005-06-15 2006-12-22 Commissariat Energie Atomique Composes permettant de placer des objets par auto-assemblage et applications
US8557351B2 (en) * 2005-07-22 2013-10-15 Molecular Imprints, Inc. Method for adhering materials together
US8808808B2 (en) 2005-07-22 2014-08-19 Molecular Imprints, Inc. Method for imprint lithography utilizing an adhesion primer layer
US8846195B2 (en) 2005-07-22 2014-09-30 Canon Nanotechnologies, Inc. Ultra-thin polymeric adhesion layer

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US5693172A (en) * 1992-10-07 1997-12-02 Zeldin; Martel Methods and compositions for interfacially bonding mineral surfaces and the like
US6190778B1 (en) * 1998-04-28 2001-02-20 Degussa-Huls Aktiengesellschaft Process for joining two solid bodies and the resultant structural element

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US5304582A (en) * 1988-04-28 1994-04-19 Matsushita Electric Industrial Co., Ltd. Process for producing polyacetylene or polyacene type long conjugated polymers
DE3832666A1 (de) * 1988-09-27 1990-04-05 Telefunken Electronic Gmbh Hochfrequenzsender, insbesondere fuer sicherungseinrichtungen
DE4234423C2 (de) * 1992-10-13 1996-10-10 Inst Mikrotechnik Mainz Gmbh Mit einem Resist beschichtete Metall- oder Halbleitersubstrate und Verfahren zur Erzielung einer stabilen Resist-Substrat-Haftung
DE19752412A1 (de) * 1996-11-27 1998-05-28 Max Planck Gesellschaft Verfahren zur Verbindung zweier Festkörper sowie ein Bauelement und ein Verfahren zur Trennung der zwei Festkörper
EP1176422B1 (fr) * 2000-07-27 2004-10-06 Micronas Holding GmbH Puces détectrices à multicouches composées de polysiloxanes
ATE355525T1 (de) * 2000-07-27 2006-03-15 Micronas Holding Gmbh Auf einer oberfläche befestigte multifunktionelle polymere-netzwerke für sensorchips
DE10137376A1 (de) * 2001-07-31 2003-02-27 Infineon Technologies Ag Geklebte Chip- und Waferstapel

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5693172A (en) * 1992-10-07 1997-12-02 Zeldin; Martel Methods and compositions for interfacially bonding mineral surfaces and the like
US6190778B1 (en) * 1998-04-28 2001-02-20 Degussa-Huls Aktiengesellschaft Process for joining two solid bodies and the resultant structural element

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
STEINKIRCHNER J ET AL: "SILICON WAFER BONDING VIA DESIGNED MONOLAYERS" ADVANCED MATERIALS, VCH VERLAGSGESELLSCHAFT, WEINHEIM, DE, Bd. 7, Nr. 7, 1. Juli 1995 (1995-07-01), Seiten 662-665, XP000520485 ISSN: 0935-9648 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008032128A1 (fr) * 2006-09-15 2008-03-20 National Center Of Scientific Research ''demokritos'' Technique d'assemblage
GR20060100518A (el) * 2006-09-15 2008-04-15 Εθνικο Κεντρο Ερευνας Φυσικων Επιστημων (Εκεφε) "Δημοκριτος" Μεθοδος συγκολλησης

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Publication number Publication date
WO2004017071A3 (fr) 2004-05-27
DE10237280A1 (de) 2004-03-11
AU2003266280A1 (en) 2004-03-03

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