CN1919953A - 在管芯粘结胶粘剂中作为助粘剂的羟基喹啉和羟基喹啉衍生物 - Google Patents

在管芯粘结胶粘剂中作为助粘剂的羟基喹啉和羟基喹啉衍生物 Download PDF

Info

Publication number
CN1919953A
CN1919953A CNA2006101265039A CN200610126503A CN1919953A CN 1919953 A CN1919953 A CN 1919953A CN A2006101265039 A CNA2006101265039 A CN A2006101265039A CN 200610126503 A CN200610126503 A CN 200610126503A CN 1919953 A CN1919953 A CN 1919953A
Authority
CN
China
Prior art keywords
resin
hydroxyquinoline
weight
die attach
composition
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
CNA2006101265039A
Other languages
English (en)
Inventor
O·M·穆扎
H·R·库德尔
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
National Starch and Chemical Investment Holding Corp
Original Assignee
National Starch and Chemical Investment Holding Corp
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 National Starch and Chemical Investment Holding Corp filed Critical National Starch and Chemical Investment Holding Corp
Publication of CN1919953A publication Critical patent/CN1919953A/zh
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C09J139/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Adhesives based on derivatives of such polymers
    • C09J139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • 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
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • C09J139/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Adhesives based on derivatives of such polymers
    • 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
    • H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/291—Material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29101—Material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of less than 400°C
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/2919—Material with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29199—Material of the matrix
    • H01L2224/2929—Material of the matrix with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29317—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than or equal to 400°C and less than 950°C
    • H01L2224/29324—Aluminium [Al] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29338—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than or equal to 950°C and less than 1550°C
    • H01L2224/29339—Silver [Ag] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29338—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than or equal to 950°C and less than 1550°C
    • H01L2224/29344—Gold [Au] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29338—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than or equal to 950°C and less than 1550°C
    • H01L2224/29347—Copper [Cu] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29338—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than or equal to 950°C and less than 1550°C
    • H01L2224/29355—Nickel [Ni] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29363—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than 1550°C
    • H01L2224/29364—Palladium [Pd] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29363—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than 1550°C
    • H01L2224/29369—Platinum [Pt] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29363—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than 1550°C
    • H01L2224/2937—Zirconium [Zr] as principal constituent
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/29386—Base material with a principal constituent of the material being a non metallic, non metalloid inorganic material
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/29386—Base material with a principal constituent of the material being a non metallic, non metalloid inorganic material
    • H01L2224/29388—Glasses, e.g. amorphous oxides, nitrides or fluorides
    • 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
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/29393—Base material with a principal constituent of the material being a solid not provided for in groups H01L2224/293 - H01L2224/29391, e.g. allotropes of carbon, fullerene, graphite, carbon-nanotubes, diamond
    • 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
    • H01L2224/838—Bonding techniques
    • H01L2224/8385—Bonding techniques using a polymer adhesive, e.g. an adhesive based on silicone, epoxy, polyimide, polyester
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/00013—Fully indexed content
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01004—Beryllium [Be]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01005—Boron [B]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01006—Carbon [C]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01013—Aluminum [Al]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01015—Phosphorus [P]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/0102—Calcium [Ca]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01024—Chromium [Cr]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01025—Manganese [Mn]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01027—Cobalt [Co]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01029—Copper [Cu]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/0103—Zinc [Zn]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01033—Arsenic [As]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/0104—Zirconium [Zr]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01046—Palladium [Pd]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01047—Silver [Ag]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/0105—Tin [Sn]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01056—Barium [Ba]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01059—Praseodymium [Pr]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01068—Erbium [Er]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01078—Platinum [Pt]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01079—Gold [Au]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01082—Lead [Pb]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/013—Alloys
    • H01L2924/0133—Ternary Alloys
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/013—Alloys
    • H01L2924/014—Solder alloys
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/049—Nitrides composed of metals from groups of the periodic table
    • H01L2924/0495—5th Group
    • H01L2924/04953—TaN
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/06—Polymers
    • H01L2924/0665—Epoxy resin
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/06—Polymers
    • H01L2924/078—Adhesive characteristics other than chemical
    • H01L2924/07802—Adhesive characteristics other than chemical not being an ohmic electrical conductor
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/102—Material of the semiconductor or solid state bodies
    • H01L2924/1025—Semiconducting materials
    • H01L2924/10251—Elemental semiconductors, i.e. Group IV
    • H01L2924/10253—Silicon [Si]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/11—Device type
    • H01L2924/14—Integrated circuits
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/181—Encapsulation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Die Bonding (AREA)

Abstract

管芯粘结胶粘组合物包括作为助粘剂的羟基喹啉或羟基喹啉衍生物。一种示范性的羟基喹啉衍生物的结构式如图。

Description

在管芯粘结胶粘剂中作为助粘剂的羟基喹啉和羟基喹啉衍生物
技术领域
[0001]本发明涉及含有作为助粘剂(adhension promoters)的羟基喹啉和羟基喹啉衍生物的管芯粘结胶粘剂(die attach adhesives)。
背景技术
[0002]在半导体封装的制造和装配中，集成电路芯片(chip)或管芯(die)用胶粘剂和丝焊粘结在引线框上，芯片和内部引线框组装件被封装在模塑树脂中。封装之后，引线框的外侧引线被粘结到印制电路板或其它外部设备。引线框或印制线路板上的任何暴露的铜表面由于暴露于空气而遭受氧化，常规地涂覆以抗氧化剂。然而，怀疑抗氧化剂的存在会干扰在半导体封装的制造以及其与印制电路板连接中的管芯粘结、丝焊(wire bonding)、封装和最终焊接操作期间的胶接工艺。
发明概述
[0003]本发明是管芯粘结胶粘剂组合物，其包括可固化树脂，可选的树脂固化剂，填料，和羟基喹啉或羟基喹啉衍生物。这些组合物中的羟基喹啉或羟基喹啉衍生物(下文称为羟基喹啉)起到助粘剂的作用。如此处所用，术语“羟基喹啉(quinolinol)”与“羟基喹啉(hydroxyquinoline)”同义。
发明详述
[0004]本发明的助粘剂是羟基喹啉化合物或衍生于羟基喹啉的化合物(下文称为羟基喹啉衍生物)，羟基喹啉衍生物是指含有羟基喹啉部分的化合物。示例性羟基喹啉化合物是：
Figure A20061012650300061
[0005]示例性羟基喹啉衍生物是那些具有下面的双-羟基喹啉结构的物质：
Figure A20061012650300062
其可以通过羟基官能化的喹啉与选择的二酸经由费歇尔酯化反应来制备。在羟基喹啉官能团之间的桥接的属性是由酸的结构确定的。通过选择适当的二酸可以控制性质诸如熔点和溶解度。
[0006]所述反应可以通过此处的反应方案来示范，其中R是任意有机部分：
具体的合适化合物包括那些其中R是烷基的化合物，特别地，R是戊基、己基、庚基或辛基基团的那些化合物。其它化合物包括那些其中R是有机基团的化合物。由于它们具有增加的分子量，这些化合物具有降低的挥发性。
[0007]其它羟基喹啉衍生物由下面的化合物示范，它们含有可聚合的官能团并且在固化期间被反应进入管芯粘结组合物；结果，在增加的温度下它们不会挥发，它们的使用减少了空隙形成。例子包括下列：
化合物A                     化合物B                 和化合物C
Figure A20061012650300071
[0008]在上面的化合物A、B和C中的反应活性官能团分别是丙烯酸酯、苯乙烯和马来酰亚胺官能团。其它合适的反应活性官能团包括环氧化物、氧杂环丁烷、苯并三唑、肉桂基化合物、苯乙烯化合物和乙烯基醚。
[0009]这些化合物和类似化合物的合成在有机合成领域技术人员的专业之内；化合物A、B和C的合成方案被显示在此：：
Figure A20061012650300072
本领域技术人员应当理解，其它的官能团可以通过类似的反应而被构建到这些化合物中。
[0010]在一种实施方案中，可固化树脂存在的量将是10％重量至99.5％重量；固化剂将以有效量存在，典型地是多达30％重量；填料如果存在的话，其存在量将是可多达90％重量；助粘剂将以有效量存在，可以是多达30％重量。在典型的实施方案中，助粘剂以低水平存在，更通常地是0.1％重量至10％重量。
[0011]用于组合物的合适的可固化树脂包括热固性聚合物和热塑性聚合物，特别是选自环氧化物、马来酰亚胺(包括双马来酰亚胺)、丙烯酸酯和甲基丙烯酸酯以及氰酸酯。其它有用的树脂包括乙烯基醚、乙烯基硅烷、硫醇-烯(thiol-enes)，和含有与芳香环连接并与该芳香环中的不饱和共轭的碳碳双键(如衍生于肉桂基的化合物和苯乙烯起始化合物)的树脂，以及延胡索酸酯和马来酸酯。
[0012]其它示例性聚合物包括聚酰胺、苯氧基化合物、苯并嗪、聚苯并嗪、聚醚砜、聚酰亚胺、硅化烯烃(siliconized olefin)、聚烯烃、聚酯、聚苯乙烯、聚碳酸酯、聚丙烯、聚氯乙烯、聚异丁烯、聚丙烯腈、聚乙酸乙烯酯、聚(2-乙烯吡啶)、顺-1，4-聚异戊二烯、3，4-聚氯丁二烯、乙烯基共聚物、聚环氧乙烷、聚乙二醇、聚甲醛、聚乙醛、聚(b-丙醇酸内酯)(poly(b-propiolacetone))、聚(10-癸酸酯)、聚对苯二甲酸乙二酯、聚己内酰胺、聚(11-十一酰胺)(poly(11-undecanoamide))、聚对苯二甲酰间苯二胺、聚四亚甲基间苯磺酰胺(poly(tetramethylene-m-benzenesulfonamide))、聚酯型聚芳基化合物、聚苯醚、聚苯硫醚、聚砜、聚醚酮、聚醚酰亚胺、氟化聚酰亚胺、聚酰亚胺硅氧烷(polyimide siloxane)、聚异吲哚并喹唑啉二酮(poly-isoindolo-quinazolinedione)、聚硫醚酰亚胺(polythioetherimide)聚苯基喹喔啉、聚喹喔酮(polyquinixalone)、酰亚胺-芳基醚苯基喹喔啉共聚物、聚喹喔啉、聚苯并咪唑、聚苯并唑、聚降冰片烯、聚芳撑醚(poly(arylene ether))、聚硅烷、聚对二甲苯、苯并环丁烯、羟基-(苯并唑)共聚物和poly(silarylene siloxanes)。
[0013]合适的氰酸酯树脂包括那些具有一般结构
Figure A20061012650300081
的树脂，其中n是1或更大，X是烃基团。示例性的X实体包括但不限于双酚A、双酚F、双酚S、双酚E、双酚O、苯酚或甲酚线型酚醛、二环聚戊二烯、聚丁二烯、聚碳酸酯、聚氨酯、聚醚或聚酯。商业上可获得的氰酸酯材料包括：AroCy L-10、AroCy XU366、AroCy XU371、AroCyXU378、XU71787.02L和XU71787.07L，供应自Huntsman LLC；PrimasetPT30、Primaset PT30 S75、Primaset PT60、Primaset PT60S、PrimasetBADCY、Primaset DA230S、Primaset MethylCy和Primaset LECY，供应自Lonza Group Limited；2-烯丙基苯酚氰酸酯、4-甲氧基苯酚氰酸酯、2，2-双(4-氰氧基苯酚)-1，1，1，3，3，3-六氟丙烷、双酚A氰酸酯、二烯丙基双酚A氰酸酯、4-苯基苯酚氰酸酯、1，1，1-三(4-氰氧基苯基)-乙烷、4-枯基酚氰酸酯、1，1-双(4-氰氧基-苯基)乙烷、2，2，3，4，4，5，5，6，6，7，7-十一氟-辛二醇二氰酸酯和4，4′-双酚氰酸酯，供应自Oakwood Products，Inc.。
[0014]其它合适的氰酸酯包括具有结构
Figure A20061012650300091
的氰酸酯，其中R1至R4独立为氢、C1-C10烷基、C3-C8环烷基、C1-C10烷氧基、卤素、苯基、苯氧基和部分或完全氟化的烷基或芳基基团(例子为1，3-苯二氰酸酯(phenylene-1，3-dicyanate))；
[0015]氰酸酯，具有结构：
Figure A20061012650300092
其中R1至R5独立为氢、C1-C10烷基、C3-C8环烷基、C1-C10烷氧基、卤素、苯基、苯氧基和部分或完全氟化的烷基或芳基基团；
[0016]氰酸酯，具有结构：
其中R1至R4独立为氢、C1-C10烷基、C3-C8环烷基、C1-C10烷氧基、卤素、苯基、苯氧基和部分或完全氟化的烷基或芳基基团；Z为化学键或SO2、CF2、CH2、CHF、CHCH3、异丙基、六氟异丙基、C1-C10烷基、O、N＝N、R8C＝CR8(其中R8是H、C1-C10烷基、或芳基)、R8COO、R8C＝N、R8C＝N-C(R8)＝N、C1-C10烷氧基、S、Si(CH3)2或下列结构之一：
Figure A20061012650300101
(例子是来自Vantico的商业名称为AroCy L-10的4，4′亚乙基双亚苯基氰酸酯)；
[0017]氰酸酯，具有结构：
Figure A20061012650300102
其中R6是氢或C1-C10烷基，X是CH2或下列结构之一：
Figure A20061012650300103
n是从0至20的数(例子包括来自Vantico的商业产品XU366和XU71787.07)；
[0018]具有结构：N≡C-O-R7-O-C≡N的氰酸酯，和
[0019]氰酸酯，其具有结构：N≡C-O-R7，其中R7是具有3至12个碳原子的非芳香烃链，所述烃链可以任选地被部分或完全氟化。
[0020]合适的环氧树脂包括双酚型、萘型和脂族型环氧。可以经商业途径得到的材料包括双酚型环氧树脂(Epiclon 830LVP，830CRP，835LV，850CRP)，可以从Dainippon Ink & Chemicals，Inc.得到；萘型环氧(Epiclon HP4032)，可以从Dainippon Ink & Chemicals，Inc.得到；脂族型环氧树脂(Araldite CY179，184，192，175，179)，可以从CibaSpecialty Chemicals得到，(Epoxy 1234，249，206)，可以从DowCorporation得到，和(EHPE-3150)，可以从Daicel Chemical Industries，Ltd.得到。
[0021]其它合适的环氧树脂包括脂环系环氧树脂、双酚-A型环氧树脂、双酚-F型环氧树脂、环氧-线型酚醛树脂、联苯型环氧树脂、萘型环氧树脂和二环聚戊二烯酚(dicyclopentadienephenol)型环氧树脂。
[0022]合适的马来酰亚胺树脂包括那些具有一般结构
Figure A20061012650300111
的树脂，其中n是1至3，X1是脂族或芳族基团。示例性X1实体包括聚丁二烯、聚碳酸酯、聚氨酯、聚醚、聚酯、简单烃和含有诸如羰基、羧基、酰胺、氨基甲酸酯、脲、酯或醚的官能团的简单烃。这些类型的树脂是商业可得的，例如可以从Dainippon Ink and Chemicals，Inc.获得。
[0023]另外的合适的马来酰亚胺树脂包括但不限于固体芳族双马来酰亚胺(BMI)树脂，特别是那些具有结构
Figure A20061012650300112
的树脂，其中Q是芳香基团。示例性芳基包括：
Figure A20061012650300113
Figure A20061012650300121
Figure A20061012650300122
其中n为1-3，
具有这些Q桥连基团的双马来酰亚胺树脂是商业可得的，例如可以从Sartomer(美国)或HOS-Technic GmbH(奥地利)获得。
[0024]其它合适的马来酰亚胺树脂包括下列：
其中C36表示具有36个碳原子的直链或分支烃链(具有或没有环部分)；
Figure A20061012650300125
[0025]合适的丙烯酸酯和甲基丙烯酸酯树脂包括那些具有一般结构
Figure A20061012650300131
的树脂，其中n为1至6，R1是-H或-CH3。X2是芳基或脂族基团。示例性X2实体包括聚丁二烯、聚碳酸酯、聚氨酯、聚醚、聚酯、简单烃和含有诸如羰基、羧基、酰胺、氨基甲酸酯、脲、酯或醚的官能团的简单烃。商业可得的材料包括(甲基)丙烯酸丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸异癸酯、(甲基)丙烯酸n-月桂酯、(甲基)丙烯酸烷基酯、(甲基)丙烯酸十三烷酯、(甲基)丙烯酸n-硬脂醇酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸四氢糠酯、(甲基)丙烯酸2-苯氧乙酯、(甲基)丙烯酸异冰片酯、1，4-丁二醇二(甲基)丙烯酸酯、1，6-己二醇二(甲基)丙烯酸酯、1，9-壬二醇二(甲基)丙烯酸酯(1，9-nonandiol di(meth)acrylate)、(甲基)丙烯酸全氟辛基乙酯(perfluorooctylethyl(meth)acrylate)、1，10-癸二醇二(甲基)丙烯酸酯(1，10-decandiol di(meth)acrylate)、壬基苯酚聚丙氧基化(甲基)丙烯酸酯(nonylphenol polypropoxylate(meth)acrylate)以及polypentoxylatetetrahydrofurfuryl acrylate，供应自Kyoeisha Chemcial Co.，LTD；聚丁二烯氨基甲酸酯二甲基丙烯酸酯(CN302、NTX6513)和聚丁二烯二甲基丙烯酸酯(CN301、NTX6039、PRO6270)，供应自Sartomer Company，Inc.；聚碳酸酯氨基甲酸酯二丙烯酸酯(ArtResin UN9200A)，供应自Negami Chemical Industries Co.，LTD；丙烯酸酯化脂族氨基甲酸酯低聚物(acrylated aliphatic urethane oligomer)(Ebecryl 230、264、265、270、284、4830、4833、4834、4835、4866、4881、4883、8402、8800-20R、8803、8804)，供应自Radcure Specialities Inc.；聚酯丙烯酸酯低聚物(Ebecryl 657、770、810、830、1657、1810、1830)，供应自RadcureSpecialities，Inc.；和环氧丙烯酸酯树脂(CN104、111、112、115、116、117、118、119、120、124、136)，供应自Sartomer Company，Inc.。在一个实施方案中，丙烯酸酯树脂选自丙烯酸异冰片酯、甲基丙烯酸异冰片酯、丙烯酸月桂酯、甲基丙烯酸月桂酯、带有丙烯酸酯官能团的聚丁二烯以及带有甲基丙烯酸酯官能团的聚丁二烯。
[0026]合适的乙烯基醚树脂是含有乙烯基醚官能团的任何树脂，包括聚丁二烯、聚碳酸酯、聚氨酯、聚醚、聚酯、简单烃和含有诸如羰基、羧基、酰胺、氨基甲酸酯、脲、酯或醚的官能团的简单烃。商业可得的树脂包括环己烷二甲醇二乙烯基醚(cyclohenanedimethanoldivinylehter)、十二烷基乙烯基醚(dodecylvinylether)、环己基乙烯基醚(cyclohexyl vinylether)、2-乙基己基乙烯基醚、双丙二醇二乙烯基醚(dipropyleneglycol divinylether)、己二醇二乙烯基醚(hexanedioldivinylether)、十八烷基乙烯基醚(octadecylvinylether)和丁二醇二乙烯基醚，供应自International Speciality Products(ISP)；Vectomer 4010、4020、4030、4040、4051、4210、4220、4230、4060、5015，供应自Sigma-Aldrich，Inc。
[0027]固化剂可以是自由基引发剂或离子型引发剂(阳离子或阴离子)，取决于选择的是自由基固化树脂还是离子固化树脂，并且将以有效量存在。对于自由基固化剂而言，有效量按重量计算一般为有机化合物(不包括任何填料)的0.1％至10％，但是可以高达按重量计算30％。对于离子型固化剂或引发剂而言，有效量按重量计算一般为有机化合物(不包括任何填料)的0.1％至10％，但是可以高达按重量计算30％。固化剂的例子包括咪唑、叔胺、有机金属盐、胺盐和改性咪唑化合物、无机金属盐、酚类、酸酐和其它这样的化合物。
[0028]示例性咪唑包括但不限于：2-甲基-咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-乙基4-甲基-咪唑、1-苄基-2-甲基咪唑、1-丙基-2-甲基-咪唑、1-氰基-乙基-2-甲基咪唑、1-氰基乙基-2-乙基-4-甲基咪唑、1-氰基乙基-2-十一烷基咪唑、1-氰基乙基-2-苯基咪唑、1-胍氨乙基-2-甲基咪唑和咪唑与偏苯三酸的加成产物。
[0029]示例性叔胺包括但不限于：N，N-二甲基苄胺、N，N-二甲基苯胺、N，N-二甲基甲苯胺、N，N-二甲基对甲氧基苯胺、对-卤代-N，N-二甲基苯胺、2-N-乙基苯胺基乙醇、三正丁胺、吡啶、喹啉、N-甲基吗啉、三乙醇胺、三亚乙基二胺、N，N，N′，N′-四甲基丁烷二胺、N-甲基哌啶。其它合适的含氮化合物包括双氰胺、二烯丙基三聚氰胺、二氨基顺丁烯二腈、胺盐和改性咪唑化合物。
[0030]示例性酚类包括但不限于：苯酚、甲酚、二甲苯酚、间苯二酚、线性酚醛树脂和间苯三酚。
[0031]示例性有机金属盐包括但不限于：环烷酸铅、硬脂酸铅、环烷酸锌、辛酸锌、油酸锡、顺丁烯二酸二丁基锡、环烷酸锰、环烷酸钴和乙酰丙酮铁(acetyl aceton iron)。其它合适的金属化合物包括但不限于：金属乙酰丙酮酸盐(metal acetoacetonate)、金属辛酸盐、金属乙酸盐、金属卤化物、金属咪唑络合物、Co(II)(乙酰丙酮酸)(Co(II)(acetoacetonate))、Cu(II)(乙酰丙酮酸)(Cu(II)(acetoacetonate))、Mn(II)(乙酰丙酮酸)(Mn(II)(acetoacetonate))、Ti(乙酰丙酮酸)(Ti(acetoacetonate))和Fe(II)(乙酰丙酮酸)(Fe(II)(acetoacetonate))。示例性无机金属盐包括但不限于：氯化锡、氯化锌和氯化铝。
[0032]示例性过氧化物包括但不限于：过氧化苯甲酰、月桂酰过氧化物、辛酰过氧化物(octanoyl peroxide)、过辛酸丁酯(butyl peroctoate)、过氧化二枯基、过氧化乙酰、对氯过氧化苯甲酰和二-叔丁基邻羧酸过苯二甲酸酯(di-t-butyl diperphthalate)；
[0033]示例性酸酐包括但不限于：马来酸酐、邻苯二甲酸酐、月桂酸酐、1，2，4，5-苯四酸酐、1，2，4-苯三酸酐、六氢邻苯二甲酸酐、六氢均苯四酸酐(hexahydropyromellitic anhydride)和六氢偏苯三酸酐(hexahydrotrimellitic anhydride)。
[0034]示例性偶氮化合物包括但不限于：偶氮异丁腈、2，2′-偶氮二丙烷、2，2′-偶氮双(2-甲基丁腈)、m，m′-偶氮氧化苯乙烯(m，m′-azoxystyrene)。其它合适的化合物包括腙(hydrozones)、己二酸二酰肼和BF3-胺络合物。
[0035]在一些情况下，使用不止一种类型的固化可能是被期望的。例如，阳离子和自由基引发可能都是期望的，在该情况下，自由基固化和离子固化树脂可以被用在组合物中。例如，这样的组合物将允许例如，固化过程通过使用紫外光照射的阳离子引发而开始，并且在后来的处理步骤中，通过施加热的自由基引发而结束。
[0036]在一些系统中，除了固化剂，固化促进剂可以被用于优化固化速率。固化促进剂包括但不限于金属环烷酸盐、金属乙酰丙酮酸盐(螯合物)、金属辛酸盐、金属乙酸盐、金属卤化物、金属咪唑络合物、金属胺络合物、三苯膦、烷基取代的咪唑、咪唑盐及硼酸盐(oniumborate)。
[0037]取决于最终应用，一种或多种填料可以被包括在组合物中，并且通常被加入是用于改进流变性质和减小应力。合适的不导电填料的例子包括氧化铝、氢氧化铝、二氧化硅、熔融二氧化硅、热解二氧化硅、蛭石、云母、硅灰石、碳酸钙、二氧化钛、沙子、玻璃、硫酸钡、锆、炭黑、有机填料和卤化乙烯聚合物，例如四氟乙烯、三氟乙烯、偏二氟乙烯、乙烯基氟、偏二氯乙烯和乙烯基氯。合适的导电填料包含炭黑、石墨、金、银、铜、铂、钯、镍、铝、碳化硅、氮化硼、金刚石和氧化铝。
[0038]填料颗粒可以是任何合适的尺寸，从纳米级至数毫米范围。用于任何具体最终用途的此类尺寸的选择在本领域技术人员的专业范围之内。填料可以以按总组合物的重量计算从10％至90％的量存在。在组合物中可以使用不止一种填料，并且填料可以进行或没有进行表面处理。适合的填料尺寸可以被实践者确定，但是一般而言，在20纳米至100微米的范围内。
                            实施例
[0039]实施例1.双-羟基喹啉的制备
Figure A20061012650300161
根据The Journal of Organic Chemistry，Volume 26，number 10，October 24，1961，第4078至4083页的Donald.S.Noyce and Lloyd J.Dolby，Amino-and Chloromethylation of 8-Quinlinol.Mechanism of Preponderant orthoSubstitution in Phenols under Mannich Conditions所述的步骤，通过8-羟基喹啉与过量甲醛在盐酸水溶液中的反应制备双-羟基喹啉。在配有磁搅棒、回流冷凝器和热油浴的250mL四颈圆底烧瓶中，混合8-羟基喹啉(29.0克，0.2000mol)和盐酸(37％，85mL)。起初，在混合这些试剂之后，观察到～25℃的放热量。然后加入甲醛(37％，9mL)，这导致清澈的黄色溶液变为金色溶液。混合物在回流下被加热90分钟。在该段时间期间，浓重的酸性烟雾产生。回流混合15分钟之后，结晶黄色固体从溶液中沉淀。回流之后，将混合物冷却至室温，并使其放置过夜。
[0040]14小时后，观察到，更多的固体已经结晶，并且此刻烧瓶被沉淀塞满。从清澈的金色母液中过滤黄色固体，并将其溶解在～850mL的水中。所形成的黄色溶液的pH经测量在0至1之间。浓氢氧化铵被缓慢加入以中和溶液。在pH在3和4之间时，清澈的黄色溶液转为不透明，在pH为5时，细粒开始形成。加入更多氢氧化铵，至pH为10.02。加入在90分钟内完成，并且在该时间期间，反应溶液/混合物的温度不超过27℃。
[0041]反应被混合70分钟，形成细粒大小的乳白混合物。反应的最终pH为10.08。浅灰色粉饼从混合物中被过滤出来，留下清澈的金色液体。将滤饼加入到300mL二甲基甲酰胺中，并剧烈混合30分钟。过滤之后，收集白色滤饼；滤液为浅紫色液体。接下来，将滤饼湿加到300mL丙酮中，混合30分钟，过滤。然后重复洗涤，留下白色滤饼和清澈无色滤液。将白色滤饼风干，磨成白色粉末，在真空下于50℃进一步过夜干燥。从该反应中获得36％的收率。
[0042]该物质的结构经1HNMR证实，其具有与在文献中公开的相同的峰，纯度为大约95％，双-羟基喹啉的DSC结果表明，mp为285℃，其值与在文献中找到的熔点匹配。TGA结果表明，在200℃的重量损失仅为1.2％。
[0043]实施例2.羟基喹啉/哌啶的制备
羟基喹啉可以是挥发性的，在本实施例中，羟基喹啉/哌啶衍生物被制备，目的是增加体积并降低羟基喹啉的挥发性。该衍生物的不对称性促成了比所发现的双-羟基喹啉熔点低的熔点。羟基喹啉/哌啶是通过等摩尔量的8-羟基喹啉、哌啶和低聚甲醛的反应在熔融状态被制备的。
[0044]将8-羟基喹啉(29.0克，0.2000mol)、哌啶(17.0克，0.2000mol)和低聚甲醛(6.0克，0.2000mol)加入配有机械混合器、温度计和回流冷凝器的100mL三颈圆底烧瓶中。随着混合，固体部分地溶解为不透明的金色液体，并且反应温度在5分钟之内从室温升至71℃。继续混合直到反应温度降至～60℃。此刻，将烧瓶放置在预热至100℃的热油浴中。反应在油浴中被混合～3.5小时，在该时间期间，反应温度在80与90℃之间变化。
[0045]在反应结束时，产物为深琥珀色浆体。在85℃，通过Kugelrohr设备将残留的原材料从浆中去除。将所形成的清澈的金色粘性液体(33克)与33mL石油醚组合并研磨。从而，从浆中形成了暗象牙色粉末。将该粉末在石油醚中再洗两次，并且在真空炉中于70℃干燥两天。该物质的结构经1HNMR和GC/MS证实，结果符合那些发现于文献中的结果。从该反应获得了41％的收率。116℃的DSC熔点与在文献中发现的熔点匹配(Donald.S.Noyce and Lloyd J.Dolby，Amino-andChloromethylation of 8-Quinlinol.Mechanism of Preponderant orthoSubstitution in Phenols under Mannich Conditions，The Journal of OrganicChemistry，Volume 26，number 10，October 24，1961，4078-4083)。
[0046]实施例3.羟基官能化羟基喹啉的制备
通过等摩尔量的8-羟基喹啉与甲醛在盐酸水溶液中反应，制备羟基官能化羟基喹啉中间体。(注意，羟基喹啉被类似地制备，但是相对于8-羟基喹啉，使用摩尔过量的甲醛)。该反应的产物显示了相比双-羟基喹啉改进的溶解度，并且更容易被表征。合成方法获自Donald.S.Noyceand Lloyd J.Dolby，Amino-and Chloromethylation of 8-Quinlinol.Mechanism of Preponderant ortho Substitution in Phenols under MannichConditions，The Journal of Organic Chemistry，Volume 26，number 10，October 24，1961，4078-4083。
[0047]在配有磁搅棒、温度计、回流冷凝器和热油浴的1升的四颈圆底烧瓶中，混合8-羟基喹啉(120.0克，0.8267mol)、盐酸(37％，352mL)和甲醛(37％，67.7克)。混合这些试剂之后，观察到～20℃的放热量。反应变为清澈的金色溶液。接下来，在125℃的油浴中加热反应，黄色固体几乎立刻从溶液中沉淀出来。在回流下(95至111℃)继续加热～65分钟。然后将嫩黄色反应混合物冷却至室温。
[0048]从清澈的黄色母液中过滤固体，并将其溶解在～800mL水中。所形成的深黄色溶液的pH经测量在0至1之间。浓氢氧化铵被缓慢加入以中和溶液。在pH在3和4之间时，清澈的黄色溶液转为不透明的桔红色。在pH为5时，细粒开始形成且反应变稠。加入更多氢氧化铵，至pH为10.0。加入在50分钟内完成，并且在该时间期间，反应溶液/混合物的温度不超过35℃。反应被混合60分钟，形成细粒大小的黄浆。然后它被混合过夜，反应的最终pH为10.15。
[0049]茶色粉饼从混合物中被过滤出来，留下深琥珀色液体。将滤饼加入到500mL二甲基甲酰胺中，并剧烈混合30分钟。过滤之后，收集白色滤饼；滤液为清澈的浅金色液体。然后重复用水洗涤。将白色滤饼风干，磨成粉末，在真空下于45℃进一步干燥过夜。从该反应获得了42％的收率。经1HNMR和GC/MS证实该物质的结构。另外，进行DSC扫描，得出137℃的熔点，这与发现于上述参考文献中的138-139℃的熔点非常接近。
[0050]实施例4：作为助粘剂的性能。
测试来自实施例1的双-羟基喹啉(bis-Q)作为管芯粘结胶粘剂中的助粘剂的效果，所述管芯粘结胶粘剂被制备为含有30份重量的双马来酰亚胺树脂、70份重量的丙烯酸酯树脂，和17.1份重量的聚丁二烯。以15％重量将此树脂制剂与85％重量的银片(silver flake)混合，用作对照组合物。
[0051]制备两个另外的样品，其中一个含有14.5％重量的树脂制剂、0.5％重量的来自实施例1的bis-Q和85％重量的银片，第二个含有14％重量的树脂制剂、1.0％重量的来自实施例1的bis-Q和85％重量的银片。用Dage管芯抗切强度测试机(Dage Die Shear Tester)测试这些组合物的胶粘强度。将每一组合物布置在5×5密耳的硅管芯和涂覆有铜的引线框之间，达10密耳厚度，并根据此处描述的固化方案使其固化，其中Cu是铜，Ag是银，PPF是含有Ni/Pd/Au合金的预电镀引线框，HW是热/湿，DSS是管芯抗切强度。
[0052]Cu-HW-DSS：30分钟内从25℃上升至175℃，在175℃保持15分钟，在240℃保持1分钟(丝焊仿真(wire bond simulation))，在175℃保持4小时(模塑后烘干仿真(post mold bake stimulation))，在121℃/100％相对湿度下保持16小时(压力锅实验环境)。
[0053]Cu-HW-DSS+5分钟270℃：30分钟内从25℃上升至175℃，在175℃保持15分钟，在240℃保持1分钟(丝焊仿真)，在175℃保持4小时(模塑后烘干仿真)，在121℃/100％相对湿度下保持16小时(压力锅实验环境)，在270℃保持5分钟。
[0054]测试每一样品的管芯抗切强度并且对每一样品的每种测试进行4次。收集结果并取其平均，管芯抗切强度(DSS)在表A中以千克力(Kgforce)表示。结果表明，双-羟基喹啉的添加改进了粘合。
               表A.管芯抗切强度，以千克力表示
  Cu-HW-DSS   Cu-HW-DSS+5分钟270℃
  实施例4的组合物   0.5   0.8
  实施例4的组合物加0.5％Bis-Q   1.12   2.3
  实施例4的组合物加1.0％Bis-Q   1.0   1.5
[0055]实施例5：作为助粘剂的性能。
测试来自实施例1的双-羟基喹啉(bis-Q)作为管芯粘结胶粘剂中的助粘剂的效果，所述管芯粘结胶粘剂被制备为含有6.5份重量的双马来酰亚胺树脂、93.5份重量的丙烯酸酯树脂，和4.0份重量的环氧树脂。将20％重量的此树脂制剂与80％重量的银片混合，用作对照组合物。对于每一涂覆有银的引线框和PPF引线框，制备两个另外的样品，其中一个含有19.5％重量的树脂制剂、0.5％重量的来自实施例1的bis-Q和80％重量的银片，第二个含有19％重量的树脂制剂、1.0％重量的来自实施例1的bis-Q和80％重量的银片。用Dage管芯抗切强度测试机测试这些组合物的粘合强度。将每一组合物布置在5×5密耳的硅管芯和涂覆有银(Ag)的引线框或涂覆有Ni/Pd/Au合金的引线框(PPF)之间，达到10密耳厚度，并根据此处描述的固化方案使其固化。
[0056]Ag-HW-DSS：30分钟内从25℃上升至175℃，在175℃保持15分钟，在240℃保持1分钟(丝焊仿真)，在175℃保持4小时(模塑后烘干仿真)，在121℃/100％相对湿度下保持16小时。
[0057]Ag-HW-DSS+5分钟270℃：30分钟内从25℃上升至175℃，在175℃保持15分钟，在240℃保持1分钟(丝焊仿真)，在175℃保持4小时(模塑后烘干仿真)，在121℃/100％相对湿度下保持16小时，在270℃保持5分钟。
[0058]PPF-HW-DSS：30分钟内从25℃上升至175℃，在175℃保持15分钟，在240℃保持1分钟(丝焊仿真)，在175℃保持4小时(模塑后烘干仿真)，在121℃/100％相对湿度下保持16小时。
[0059]PPF-HW-DSS+5分钟270℃：30分钟内从25℃上升至175℃，在175℃保持15分钟，在240℃保持1分钟(丝焊仿真)，在175℃保持4小时(模塑后烘干仿真)，在121℃/100％相对湿度下保持16小时，在270℃保持5分钟。
[0060]测试每一样品的管芯抗切强度(DSS)并且对每一样品的每种测试进行4次。收集结果并取其平均，在表B中以千克力表示。结果表明，双-羟基喹啉的添加改进了粘合。
                   表B.管芯抗切强度，以千克力表示
  AG HWDSS   AG HWDSS+5分钟270℃   PPF HWDSS   PPF HWDSS+5分钟270℃
实施例5的组合物   1.9   2.5   3.1   3.0
实施例5的组合物加0.5％Bis-Q   4.5   5.9   6.4   6.0
实施例5的组合物加1.0％Bis-Q   5.2   7.2   5.5   8.3
[0061]实施例6：作为助粘剂的性能。
测试来自实施例1的双-羟基喹啉(bis-Q)作为管芯粘结胶粘剂中的助粘剂的效力，所述管芯粘结胶粘剂被制备为含有100份重量的双马来酰亚胺树脂、7.5份重量的聚丁二烯、10份重量的肉桂基化合物，和10份重量的三乙烯基环已烯。将23％重量的此树脂配方与77％重量的银片混合并用作对照组合物。制备两个另外的样品，其中一个含有22％重量的树脂配方、1.0％重量的来自实施例1的bis-Q和77％重量的银片，第二个含有20.5％重量的树脂配方，2.5％重量的来自实施例1的bis-Q和77％重量的银片。
[0062]将每一组合物布置在5×5密耳的硅管芯和涂覆有银(Ag)的引线框或涂覆有PPF的引线框之间，达到10密耳厚度，并根据本说明书段落[0056]至[0059]中提出的固化方案将其固化。测试每一样品的管芯抗切强度并且每一样品的每种测试进行4次。收集结果并将其平均，剪切强度(DSS)结果在表C中以千克力表示。结果表明，双-羟基喹啉的添加改进了粘合。
[0063]
                   表C.管芯抗切强度，以千克力表示
  AG HWDSS   AG HWDSS+5分钟270℃   PPF HWDSS   PPF HW DSS+5分钟270℃
实施例6的组合物   2.8   0.9   0.6   0.7
实施例6的组合物加0.5％Bis-Q   5.4   3.4   1.6   1.4
实施例6的组合物加1.0％Bis-Q   4.1   2.7   1.9   1.7
[0064]实施例7：作为助粘剂的性能。
测试来自实施例3的羟基官能化羟基喹啉(OH-Q)作为管芯粘结胶粘剂中的助粘剂的效力，所述管芯粘结胶粘剂被制备为含有63.5份重量的丙烯酸酯树脂、6.5份重量的双马来酰亚胺树脂、30份重量的聚丁二烯、4份重量的烯丙基官能化环氧化合物，和1.74份重量的硫化硅烷(sulfidesilane)，和少量的过氧化物和咪唑作为固化剂。将20％重量的此树脂配方与80％重量的银片混合并用作对照组合物。对于银(Ag)和PPF引线框，为每一类型的引线框制备两个另外的样品，其中一个含有19.5％重量的树脂配方、0.5％重量的来自实施例3的OH-Q和80％重量的银片，第二个含有19％重量的树脂配方、1.0％重量的来自实施例3的OH-Q和80％重量的银片。
[0065]将每一组合物布置在5×5密耳的硅管芯和引线框之间，达到10密耳厚度，并根据本说明书段落[0056]至[0059]中提出的固化方案将其固化，并测试管芯抗切强度。每一样品的每种测试进行4次，收集结果并将其平均。剪切强度(DSS)结果在表D中以千克力表示，结果表明，羟基官能化羟基喹啉的添加改进了粘合。
[0066]
                   表D.管芯抗切强度，以千克力表示
  AG HWDSS   AG HWDSS+5分钟270℃   PPF HWDSS PPF HWDSS+5分钟270℃
实施例7的组合物   2.5   3.5   2.6 3.0
实施例7的组合物加0.5％OH-Q   8.1   8.5   8.0 10.2
实施例7的组合物加1.0％OH-Q   7.2   8.0   6.0 8.0
[0067]实施例8：作为助粘剂的性能。
测试0.5％重量水平(不包含银填料)的来自实施例2的哌啶-羟基喹啉(Pr-Q)在根据实施例7制备的对照管芯粘结胶粘剂中作为助粘剂的效力。如上述实施例，测试在银引线框和PPF引线框上的(硅管芯)管芯抗切强度。结果在表E中表示，结果表明，哌啶-羟基喹啉的添加改进了粘合。
[0068]
          表E.管芯抗切强度，以千克力表示
  AG HW DSS+5分钟270℃   PPF HW DSS+5分钟270℃
  实施例8的组合物   3.5   3.0
  实施例8的组合物加0.5％PR-Q   6.0   5.2
[0069]实施例9：作为助粘剂的性能。
测试0.5％和1.0％重量水平(不包含银填料)8-羟基喹啉(8-HQ)在根据实施例7制备的管芯粘结胶粘剂中作为助粘剂的效力。如上述实施例，测试在银引线框和PPF引线框上的(硅管芯)管芯抗切强度。结果在表F中表示，结果表明，8-羟基喹啉的添加改进了粘合。
[0070]
         表F.管芯抗切强度，以千克力表示
  AG HW DSS   PPF HW DSS
  实施例9的组合物   2.5   2.6
  实施例9的组合物加0.5％8-HQ   7.9   9.1
  实施例9的组合物加1.0％8-HQ   10.0   5.4

Claims (8)

1.具有改进粘合性的管芯粘结组合物，所述管芯粘结组合物包括可固化树脂、填料，以及可选地所述树脂的固化剂，其中所述组合物还包括作为助粘剂的羟基喹啉或羟基喹啉衍生物。
2.根据权利要求1的管芯粘结组合物，其中所述羟基喹啉或羟基喹啉衍生物选自：
Figure A2006101265030002C1
和
Figure A2006101265030003C1
其中R是任意有机部分。
3.根据权利要求1的管芯粘结组合物，其中所述羟基喹啉或羟基喹啉衍生物选自：
Figure A2006101265030003C2
4.根据权利要求1、2或3的管芯粘结组合物，其中所述可固化树脂是马来酰亚胺树脂、丙烯酸酯或甲基丙烯酸酯树脂、环氧树脂或氰酸酯树脂。
5.改进管芯粘结胶粘剂的粘合性的方法，所述管芯粘结胶粘剂包括可固化树脂、填料以及可选的树脂固化剂，所述方法包括：向该组合物中添加羟基喹啉或羟基喹啉衍生物。
6.根据权利要求5的方法，其中所述羟基喹啉或羟基喹啉衍生物选自下列：
Figure A2006101265030004C1
其中R是烷基。
7.根据权利要求5的方法，其中所述羟基喹啉或羟基喹啉衍生物选自：
8.根据权利要求5的方法，其中所述可固化树脂是马来酰亚胺树脂、丙烯酸酯或甲基丙烯酸酯树脂、环氧树脂或氰酸酯树脂。
CNA2006101265039A 2005-08-25 2006-08-22 在管芯粘结胶粘剂中作为助粘剂的羟基喹啉和羟基喹啉衍生物 Pending CN1919953A (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/211,920 2005-08-25
US11/211,920 US20070049665A1 (en) 2005-08-25 2005-08-25 Quinolinols and quinolinol derivatives as adhesion promoters in die attach adhesives

Publications (1)

Publication Number Publication Date
CN1919953A true CN1919953A (zh) 2007-02-28

Family

ID=37478757

Family Applications (1)

Application Number Title Priority Date Filing Date
CNA2006101265039A Pending CN1919953A (zh) 2005-08-25 2006-08-22 在管芯粘结胶粘剂中作为助粘剂的羟基喹啉和羟基喹啉衍生物

Country Status (10)

Country Link
US (1) US20070049665A1 (zh)
EP (1) EP1758164B1 (zh)
JP (1) JP4823809B2 (zh)
KR (1) KR101233224B1 (zh)
CN (1) CN1919953A (zh)
AT (1) ATE411614T1 (zh)
DE (1) DE602006003151D1 (zh)
PT (1) PT1758164E (zh)
SG (1) SG130162A1 (zh)
TW (1) TWI415886B (zh)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8120153B1 (en) * 2005-09-16 2012-02-21 University Of Central Florida Research Foundation, Inc. High-temperature, wirebondless, injection-molded, ultra-compact hybrid power module
US7468407B2 (en) * 2005-09-26 2008-12-23 National Starch And Chemical Investment Holding Copporation Metal salts of quinolinols and quinolinol derivatives in curable compositions
KR100918345B1 (ko) * 2007-11-23 2009-09-22 제일모직주식회사 이방 전도성 필름용　조성물　및 이를 이용한 이방 전도성필름
CN107709418B (zh) 2015-05-08 2021-04-27 汉高知识产权控股有限责任公司 可烧结的膜和膏及其使用方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2874080A (en) * 1953-07-18 1959-02-17 Deutsch Goldund Silber Scheide Self-hardening surface coating compositions
JPH05125118A (ja) * 1991-11-02 1993-05-21 Nippon Oil & Fats Co Ltd 紫外線吸収性ポリマー
JPH05247220A (ja) * 1992-02-28 1993-09-24 Nippon Steel Chem Co Ltd ８−ヒドロキシキノリン骨格を有する重合体及びその製造方法
US6482503B1 (en) * 1993-03-19 2002-11-19 Xerox Corporation Recording sheets containing pyrrole, pyrrolidine, pyridine, piperidine, homopiperidine, quinoline, isoquinoline, quinuclidine, indole, and indazole compounds
US5744533A (en) * 1997-06-04 1998-04-28 Johnson Matthey, Inc. Adhesive composition for bonding a semiconductor device
US6124374A (en) * 1998-05-29 2000-09-26 Block Drug Company, Inc. Antimicrobial denture adhesive and cleanser compositions
US6344157B1 (en) * 1999-02-12 2002-02-05 National Starch And Chemical Investment Holding Corporation Conductive and resistive materials with electrical stability for use in electronics devices
JP3816697B2 (ja) * 1999-07-07 2006-08-30 大日精化工業株式会社 重合体が結合した機能剤、その製造方法、それらの使用方法及びそれらを使用した物品
US6583201B2 (en) * 2001-04-25 2003-06-24 National Starch And Chemical Investment Holding Corporation Conductive materials with electrical stability for use in electronics devices
US20030111519A1 (en) * 2001-09-04 2003-06-19 3M Innovative Properties Company Fluxing compositions
US7108806B2 (en) * 2003-02-28 2006-09-19 National Starch And Chemical Investment Holding Corporation Conductive materials with electrical stability and good impact resistance for use in electronics devices
JP4295047B2 (ja) * 2003-06-02 2009-07-15 日本軽金属株式会社 発光性有機高分子金属錯体及び湿式製膜可能な発光性有機高分子金属錯体組成物並びにその製造方法
CN1246368C (zh) * 2004-06-18 2006-03-22 中国科学院广州化学研究所 含有8－羟基喹啉金属配合物的交联高聚物及其制法和用途

Also Published As

Publication number Publication date
DE602006003151D1 (de) 2008-11-27
EP1758164B1 (en) 2008-10-15
TWI415886B (zh) 2013-11-21
PT1758164E (pt) 2008-11-26
EP1758164A1 (en) 2007-02-28
ATE411614T1 (de) 2008-10-15
SG130162A1 (en) 2007-03-20
TW200722470A (en) 2007-06-16
JP4823809B2 (ja) 2011-11-24
KR101233224B1 (ko) 2013-02-14
KR20070024403A (ko) 2007-03-02
JP2007056265A (ja) 2007-03-08
US20070049665A1 (en) 2007-03-01

Similar Documents

Publication Publication Date Title
US7517925B2 (en) Benzoxazines, thermosetting resins comprised thereof, and methods for use thereof
US20100121022A1 (en) 1,3-dipolar cycloaddition of azides to alkynes
CN1970668A (zh) 在管芯粘结胶粘剂中作为助粘剂和助传导剂的羟基喹啉和羟基喹啉衍生物的金属盐
CN101033295A (zh) 含硅氧烷的可固化物质
KR101556802B1 (ko) 이미드 부분을 함유하는 알콜, 및 이로부터 제조된 반응성 올리고머
CN1919953A (zh) 在管芯粘结胶粘剂中作为助粘剂的羟基喹啉和羟基喹啉衍生物
TW200418948A (en) Co-curable compositions
CN1919525A (zh) 用作底层填充组合物的助熔剂和促进剂的羟基喹啉
JP6070589B2 (ja) シランカップリング剤及びその製造方法、プライマー組成物並びに塗料組成物
US6706835B2 (en) Curable compositions containing thiazole functionality
JP2011241343A (ja) 樹脂組成物及び樹脂組成物を使用して作製した半導体装置
JP2537736B2 (ja) エポキシ樹脂組成物
JPH0822901B2 (ja) 新規なエポキシ樹脂変性体及びその製造法
EP1716215B1 (en) Curable liquid compositions containing bisoxazoline
KR100683979B1 (ko) 감광성 폴리에스테르계 고분자를 포함하는 접착제 조성물및 이를 이용한 접착시트
CA2462339A1 (en) Polyepoxy compounds having an amide linkage
JPS5840378A (ja) エポキシ樹脂組成物
JPH0418443A (ja) 熱硬化性樹脂組成物

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Open date: 20070228