CN103053016A - Method for manufacturing semiconductor wafer provided with adhesive layer, photosensitive adhesive, and semiconductor device - Google Patents

Method for manufacturing semiconductor wafer provided with adhesive layer, photosensitive adhesive, and semiconductor device Download PDF

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Publication number
CN103053016A
CN103053016A CN2011800379173A CN201180037917A CN103053016A CN 103053016 A CN103053016 A CN 103053016A CN 2011800379173 A CN2011800379173 A CN 2011800379173A CN 201180037917 A CN201180037917 A CN 201180037917A CN 103053016 A CN103053016 A CN 103053016A
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China
Prior art keywords
photosensitive adhesive
resin
semiconductor wafer
methyl
adhesive layer
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CN2011800379173A
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Chinese (zh)
Inventor
森修一
藤井真二郎
满仓一行
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Showa Denko Materials Co ltd
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Hitachi Chemical Co Ltd
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
    • H01L21/52—Mounting semiconductor bodies in containers
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • H01L24/27—Manufacturing methods
    • 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
    • H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
    • H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
    • H01L2224/321—Disposition
    • H01L2224/32135—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip
    • H01L2224/32145—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip the bodies being stacked
    • 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
    • H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
    • H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
    • H01L2224/321—Disposition
    • H01L2224/32151—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/32221—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/32225—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
    • 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
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/481—Disposition
    • H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/48225—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
    • H01L2224/48227—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation connecting the wire to a bond pad of the item
    • 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
    • H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
    • H01L2224/732—Location after the connecting process
    • H01L2224/73251—Location after the connecting process on different surfaces
    • H01L2224/73265—Layer and wire connectors
    • 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
    • H01L2224/8319—Arrangement of the layer connectors prior to mounting
    • H01L2224/83191—Arrangement of the layer connectors prior to mounting wherein the layer connectors are disposed only on the semiconductor or solid-state body
    • 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
    • H01L24/73—Means for bonding being of different types provided for in two or more of groups H01L24/10, H01L24/18, H01L24/26, H01L24/34, H01L24/42, H01L24/50, H01L24/63, H01L24/71
    • 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
    • H01L2924/10—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
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/151—Die mounting substrate
    • H01L2924/153—Connection portion
    • H01L2924/1531—Connection portion the connection portion being formed only on the surface of the substrate opposite to the die mounting surface
    • H01L2924/15311—Connection portion the connection portion being formed only on the surface of the substrate opposite to the die mounting surface being a ball array, e.g. BGA
    • 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
    • H01L2924/151—Die mounting substrate
    • H01L2924/156—Material
    • H01L2924/15786—Material with a principal constituent of the material being a non metallic, non metalloid inorganic material
    • H01L2924/15788—Glasses, e.g. amorphous oxides, nitrides or fluorides
    • 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

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Die Bonding (AREA)

Abstract

Provided is a method for manufacturing a semiconductor wafer provided with an adhesive layer, which includes: a step wherein a photosensitive adhesive layer is formed by applying a photosensitive adhesive to the whole one surface of a semiconductor wafer by a screen printing method; and a step wherein the photosensitive adhesive layer is brought into a B stage by exposure.

Description

Manufacture method, photosensitive adhesive and semiconductor device with the semiconductor wafer of bond layer
Technical field
The present invention relates to a kind of manufacture method, photosensitive adhesive and semiconductor device of the semiconductor wafer with bond layer.More specifically, relate to a kind of can be as with holding components laminations such as the semiconductor element such as IC, LSI and lead frame, insulating properties support substrates, or with the semiconductor chip chips welding photosensitive adhesive of the grafting material (die-bond material) during lamination each other, use manufacture method and the semiconductor device of the semiconductor wafer of this bonding agent.
Background technology
As the grafting material of the semiconductor element such as IC, LSI and holding components or with the semiconductor chip grafting material during lamination each other, known have the adhesive film that uses specific polyimide resin, a chips welding adhesive film that has added electroconductive stuffing or inorganic filler in specific polyimide resin.
In recent years, studying technology by on semiconductor wafer (below, sometimes only be called " wafer "), carrying out the assembly process of semiconductor device together and raising the efficiency.In addition, along with the lamination of semiconductor chip, the thickness of wafer also has the tendency of filming.In general, it is applicable to use the operation of adhesive film or by spin-coating method chips welding is coated on operation on the semiconductor wafer with bonding agent.
As the operation of using adhesive film, the whole surface layer that can be set forth in semiconductor wafer is pressed adhesive film, and then lamination cutting uses supporting film, and makes its singualtion by cutting action, with lamination the semiconductor chip of adhesive film stick to method on semiconductor substrate or the semiconductor chip etc.
As the method for coating adhesive on whole of semiconductor wafer, be well-known by High Rotation Speed with the spin-coating method that the aqueous bonding agent on the semiconductor wafer is coated on its whole.
In the operation of using thin film wafers, have the tendency that die strength descends.Therefore, wish that coating chips welding bonding agent carries out the B rank under the state that is pasted with back of the body mill adhesive tape after back of the body mill (バ ッ Network グ ラ イ Application De, back grind) operation of wafer.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2008-98213 communique
Patent documentation 2: Japanese JP 5-54262 communique
Summary of the invention
The problem that invention will solve
Yet, when using adhesive film, press in the operation of adhesive film the waste that the part beyond wafer easily produces adhesive film on the wafer upper strata.In addition, when using spin-coating method, need on semiconductor wafer, to supply with bonding agent continuously, and then discarded, until form uniform bond layer, therefore easily produce the waste of bonding agent.
Further, the thermal endurance of back of the body mill adhesive tape is about 80 ℃～100 ℃, and the heating more than 100 ℃ can cause back of the body mill adhesive tape to shrink.The back of the body grinds the contraction of adhesive tape, becomes the reason of warping of semiconductor wafer.Even and the heating below 80 ℃, also can be because of the thermal coefficient of expansion of the thermal coefficient of expansion of back of the body mill adhesive tape and semiconductor wafer poor, and have the tendency of semiconductor wafer generation warpage in the cooling after heating.
The present invention In view of the foregoing carries out, its objective is provides a kind of can being wasted in uniform thickness and less bonding agent to form bond layer on the semiconductor wafer, and can avoid the used photosensitive adhesive of manufacture method, this manufacture method with the semiconductor wafer of bond layer of the warping of semiconductor wafer that causes because of the heating that is used for bond layer B rank, possessing can be by semiconductor device and the silk screen printing photosensitive adhesive with the semiconductor wafer of bond layer of this manufacture method manufacturing.
The method of dealing with problems
The invention provides a kind of manufacture method of the semiconductor wafer with bond layer, it comprises by the whole surface-coated photosensitive adhesive of silk screen print method in the one side of semiconductor wafer, forms the operation of photosensitive adhesive layer and makes the operation on photosensitive adhesive layer B rank by exposure.
According to the manufacture method of the invention described above, can be wasted in uniform thickness and less bonding agent and form bond layer on the semiconductor wafer, and can avoid the warping of semiconductor wafer that causes because of the heating that is used for bond layer B rank.
Above-mentioned photosensitive adhesive can contain thermosetting resin, radioactive ray polymerizable compound and Photoepolymerizationinitiater initiater.
Above-mentioned photosensitive adhesive can further contain the hot curing initator.
The viscosity of above-mentioned photosensitive adhesive under 25 ℃ can be 1～100Pas, and the thixotropic index of above-mentioned photosensitive adhesive can be 1.0～3.0.
Photosensitive adhesive among the present invention contains thermosetting resin, radioactive ray polymerizable compound and Photoepolymerizationinitiater initiater, and can be used to form the photosensitive adhesive layer in above-mentioned manufacture method.
The present invention also provides a kind of semiconductor device by following method gained, described method comprises and will pass through the semiconductor wafer singualtion with bond layer of the manufacture method gained of the invention described above, obtain the operation with the semiconductor chip of bond layer, and will be adhered to the semiconductor chip of the semiconductor wafer of bond layer the operation of holding components or other semiconductor chip.
Further, the invention provides a kind of silk screen printing photosensitive adhesive, it contains thermosetting resin, radioactive ray polymerizable compound and Photoepolymerizationinitiater initiater, and the viscosity under 25 ℃ is 1～100Pas, and thixotropic index is 1.0～3.0.
The invention effect
According to the present invention, provide a kind of can being wasted in uniform thickness and less bonding agent to form bond layer on the semiconductor wafer, and can avoid the used photosensitive adhesive of manufacture method, this manufacture method with the semiconductor wafer of bond layer of the warping of semiconductor wafer that causes because of the heating that is used for bond layer B rank, possess semiconductor device and the silk screen printing photosensitive adhesive of semiconductor wafer that can be by this manufacture method manufacturing.
Description of drawings
Fig. 1 is a kind of ideograph of execution mode of the manufacture method of expression semiconductor device.
Fig. 2 is a kind of ideograph of execution mode of the manufacture method of expression semiconductor device.
Fig. 3 is a kind of ideograph of execution mode of the manufacture method of expression semiconductor device.
Fig. 4 is a kind of ideograph of execution mode of the manufacture method of expression semiconductor device.
Fig. 5 is a kind of ideograph of execution mode of the manufacture method of expression semiconductor device.
Fig. 6 is the pattern sectional view of a kind of execution mode of expression semiconductor device.
Embodiment
Below, on one side with reference to accompanying drawing, on one side manufacture method, photosensitive adhesive, semiconductor device and the silk screen printing of the semiconductor wafer with bond layer of the present invention preferred implementation with photosensitive adhesive is elaborated.But the present invention is not limited to following execution mode.
The manufacture method of the semiconductor device of present embodiment, comprise by the whole surface-coated photosensitive adhesive of silk screen print method in the one side of semiconductor wafer, form the photosensitive adhesive layer operation (the photosensitive adhesive layer forms operation), make the operation (B rank chemical industry order) on photosensitive adhesive layer B rank and the operation (cutting action) that the photosensitive adhesive layer of semiconductor wafer behind the B rank cut by exposure.
(the photosensitive adhesive layer forms operation)
Semiconductor wafer 6 shown in Figure 1 can be used to form interior plant semiconductor packages (semiconductor device) semiconductor chip 13a and 13b(Fig. 6 in (Fig. 6)).Semiconductor wafer 6 typical situations are silicon wafer.Semiconductor wafer 6 can also form circuit by front operation.Form in the operation at the photosensitive adhesive layer, for example, as shown in Figure 1, be coated with (printing) photosensitive adhesive 5 by silk screen print method at the opposite face of the one side with being formed with circuit of semiconductor wafer 6 (back side).Thus, as shown in Figure 2, form the photosensitive adhesive layer 7 of uniform thickness at the back side of semiconductor wafer 6.
Silk screen print method comprises following two kinds of techniques usually.One of them is to use the technique of so-called operplate printing version that is provided with the peristome of patterning at smooth metallic plate.This technique is by arranging the operplate printing version at the object that will print, and uses the metallic plate brushing that is referred to as squeegee (squeegee) to carry printing ink on the operplate printing version, thus coating printing ink.By this operation, the applied one-tenth of printing ink is the same with patterns of openings shape on being arranged on the operplate printing version.
As another kind of silk screen print method, be to use in the braiding of the silk threads such as stainless steel, nylon and polyester and in the ramify, the residual lower part that will be coated with and with the technique of the so-called mesh galley of the landfill other parts such as resin only.In this technique, brush the printing ink that carries on mesh galley with the resin that is called scraper or metal plate.By this operation, printing ink is impregnated in the mesh galley not by the peristome of the landfills such as resin.Then, use the squeegee brushing mesh galley of being made by polyurethane, silicon rubber etc.By this operation, the printing ink that soaks into to the peristome is transferred on the printing object, and finishes printing process.
In the present embodiment, any typography can optionally only be coated on bonding agent in desirable position, the zone, therefore can reduce the waste of bonding agent, and the material qualification rate is excellent.
If print in wider scope with the technique that adopts the operplate printing version, then since in the peristome without any parts, so galley can not produce stress to the pressure of the squeegee on the peristome.Therefore, pressure concentration is in the central authorities of squeegee, and the middle body of squeegee strongly is pressed in the peristome, thereby has the tendency that the thickness of photosensitive adhesive layer descends in the centre of peristome.That is to say, usually peristome is wider, and the middle body of squeegee just more strongly is pressed into, and then has the tendency of thickness decline of the photosensitive adhesive layer of centre.
On the other hand, in the technique of using mesh galley, because there is the silk of silk screen in peristome, so mesh galley has produced stress for the pressure of squeegee.That is to say, even at the middle body of squeegee, the silk that is positioned at the silk screen of peristome has also played the function as holding components, so squeegee can strongly not be pressed in the peristome.Therefore, even at the middle body of squeegee, thickness can not descend yet, and can obtain uniform photosensitive adhesive layer.
Silk screen print method in the present embodiment is considered from the viewpoint of photosensitive adhesive layer that uniform film thickness is set in the such relative broad range in the whole surface of wafer, preferably adopts the technique of mesh galley.
(B rank chemical industry order)
Above-mentioned photosensitive adhesive layer 7 is to had the photosensitive adhesive layer of cementability by sticky object carry out the B rankization by exposure after.To photosensitive adhesive layer 7 irradiation visible light or the ultraviolet ray after being coated with, make the photosensitive adhesive 5 that consists of photosensitive adhesive layer 7 carry out the B rank by exposure device.Thus, Photoepolymerizationinitiater initiater and radioactive ray polymerizable compound contained in the photosensitive adhesive 5 carry out polymerization reaction, so that the photosensitive adhesive layer 8 behind the B rank has suitable adherence and cementability.Particularly, photosensitive adhesive layer 8 is fixed on the semiconductor wafer 6.As mentioned above, do not heat, and carry out the B rank of photosensitive adhesive layer 7 by exposure, can under back of the body mill adhesive tape directly sticks on state on the semiconductor wafer 6, carry out the coating of photosensitive adhesive 5 and the B rank of photosensitive adhesive layer 7.
Consider from avoiding oxygen that photopolymerization reaction is produced the viewpoint that hinders, exposure is preferably carried out under nitrogen atmosphere or under the vacuum condition, perhaps transparent coverlay film lamination is being carried out under the state on the photosensitive adhesive layer 7.More specifically, the photosensitive adhesive layer 8 on B rank by exposure, have in the suitable adherence of carrying out singualtion by cutting and when cutting, can peel off from support, and with respect to semiconductor chip and glass substrate etc. by the cementability of sticky object.For the detailed content of the photosensitive adhesive layer 8 with this function, describe hereinafter.
Viscous force (surperficial viscous force) by making the surface of photosensitive adhesive layer 8 under 30 ℃ after the exposure is 200gf/cm 2Below, can confirm that photosensitive adhesive layer 8 is able to the B rank.
If the surperficial viscous force under 30 ℃ surpasses 200gf/cm 2, then photosensitive adhesive layer 8 surface tackiness at room temperature uprises, and has the tendency that operability descends.Further, the fissility decline that also has after the cutting and cut film, the tendency that pick descends.In addition, if the surperficial viscous force under 30 ℃ is 1gf/cm 2Below, the adherence step-down of photosensitive adhesive then, water is immersed in the interface of photosensitive adhesive and cutting film when cutting, has the tendency that chip splashes.
The surperficial viscous force of photosensitive adhesive layer 8 under 120 ℃ of exposure is preferably 200gf/cm 2Above.
If the surperficial viscous force under 120 ℃ is less than 200gf/cm 2, then hot pressing is impaired, has and produce hole, the tendency of hot pressing temperature high temperature when hot pressing.In addition, the surperficial viscous force under 120 ℃ is 500gf/cm 2When above, the excessive wetting and spreading of photosensitive adhesive when having hot pressing, and photosensitive adhesive is exposed to the tendency of chip sides.
Above-mentioned surperficial viscous force is the following value of measuring.By silk screen print method photosensitive adhesive is coated on the silicon wafer, and by the parallel exposure machine of high accuracy (ORC make made, " EXM-1172-B-∞ " (trade name)), under nitrogen atmosphere with 1000mJ/cm 2Filming of gained exposed.Then, make the firmly probe viscous force testing machine of Co., Ltd. of generation section (レ ス カ society) manufacturing, at probe diameter: 5.1mm, traction peeling rate: 10mm/s, contact loading: 100gf/cm 2, time of contact: 1s condition under, the surperficial viscous force of the photosensitive adhesive layer 8 under measuring 30 ℃ and 120 ℃.Also can use parallel exposing machine (the fine jade Mi Nasi of Co., Ltd. (Le ミ Na ス) makes, " ML-210FM mask aligner " (trade name)) to replace the above-mentioned parallel exposure machine of high accuracy.
(cutting action)
Then, cut with the semiconductor wafer 20 with bond layer that is formed on the photosensitive adhesive layer 8 on its back side having semiconductor wafer 6 from wafer side, make semiconductor chip 11(Fig. 4 of singualtion).That is to say, cut off semiconductor wafer 6 by cutting machine, thereby be a plurality of semiconductor chips 11 with semiconductor wafer 6 cuttings.Before this cutting action, preferably paste cutting film 10 at the back side of the semiconductor wafer 6 that has formed above-mentioned photosensitive adhesive layer 8.Stickup can be carried out while heating as required.For example, preferably under the state that integral body is fixed in framework (wafer ring) 9 by cutting film 10 (Fig. 3), use cutter 12 to carry out (Fig. 4).The semiconductor chip 11 with the photosensitive adhesive layer of singualtion uses chips welding (die bonding) device to wait and picks up (Fig. 5).
As shown in Figure 6, will be configured on the holding components 14 of other preparation by the semiconductor chip 13a of cutting action gained.Perhaps, other semiconductor chip 13b with outside the semiconductor chip 13a is configured on the semiconductor chip 13a that is engaged in advance on the holding components 14.At this moment, by photosensitive adhesive layer 16 and 17 is carried out hot pressing, make semiconductor chip 13a and holding components 14 and semiconductor chip 13b and semiconductor chip 13a bonding, thereby semiconductor chip 13a and 13b are adhesively fixed in holding components 14 or semiconductor chip 13a.
Then, the pad (bonding pad) of semiconductor chip 13a being connected with 13b by bonding wire (bonding wire) 18 is connected with holding components 14, with encapsulant 15 semiconductor chip 13a and 13b are sealed with bonding wire 18, finish thus semiconductor packages shown in Figure 6 (semiconductor device).
According to the manufacture method of above-described semiconductor device, can only be used for bonding semiconductor chip 13a and holding components 14 or semiconductor chip 13a and 13b photosensitive adhesive 5 each other in semiconductor wafer 6 coatings by silk screen print method.Thus, regardless of the composition of photosensitive adhesive 5, can be coated with and be desirable thickness by changing galley.Therefore, can reduce semiconductor device or with the waste of the bonding agent in the manufacture method of the semiconductor wafer of bond layer, and can be multiple thickness with single bonding agent coating.
Then, the preferred implementation of the photosensitive adhesive in the present embodiment described.This photosensitive adhesive can be suitably as the above-mentioned photosensitive adhesive 5 in the manufacture method of above-mentioned semiconductor device.
Photosensitive adhesive in the present embodiment contains (A) thermosetting resin, (B) radioactive ray polymerizable compound and (C) Photoepolymerizationinitiater initiater.
(A) thermosetting resin, so long as by the formed composition of reactive compounds that produces cross-linking reaction by heating, just be not particularly limited, for example, can enumerate epoxy resin, isocyanate resin, maleimide resin, pi-allyl Na Dike imide resin, phenolic resins, urea resin, melamine resin, alkyd resins, acrylic resin, unsaturated polyester resin, diallyl phthalate resin, organic siliconresin, resorcinol formaldehyde resin, xylene resin, furane resins, polyurethane resin, ketone resin, the cyanacrylate resin, polyisocyanate resin, the resin that contains three (2-hydroxyethyl) isocyanuric acid ester, the resin that contains the trimellitic acid triallyl, by the synthetic thermosetting resin of cyclopentadiene, and the thermosetting resin that passes through the trimerization gained of aromatic series cynoguanidine.Wherein, with the combination of polyimide resin in, consider preferred epoxy, maleimide resin and pi-allyl Na Dike imide resin from the viewpoint that can at high temperature have excellent bonding force.In addition, these thermosetting resins can use separately a kind or will be used in combination more than 2 kinds.
As epoxy resin, preferably contain the material of at least 2 above epoxy radicals at molecule, and consider from the viewpoint of hot pressing, curing property and solidfied material characteristic, more preferably the epoxy resin of the glycidol ether type of phenol.As this resin, for example, can enumerate glycidol ether, the bisphenol-A phenolic varnish gum of glycidol ether, the cresols novolac resin of glycidol ether, the phenol novolac resin of glycidol ether, the propylene oxide adduct bisphenol A-type of glycidol ether, the ethylene oxide adduct bisphenol A-type of glycidol ether, the hydrogenated bisphenol A type of bisphenol A-type (or AD type, S type, F type) glycidol ether,
The ethylene oxidic ester of the glycidol ether of the glycidol ether of naphthalene resin, 3 functional-type (or 4 functional-type), the glycidol ether of bicyclopentadiene phenolic resins, dimeric dibasic acid, the glycidyl amine of 3 functional-type (or 4 functional-type) and the glycidyl amine of naphthalene resin etc.They can use separately a kind maybe can will be used in combination more than 2 kinds.
Particularly chloride ion, water-disintegrable chlorine etc. are reduced to high-purity thing below the 300ppm as epoxy resin, from preventing electromigration, preventing the viewpoint of metallic conductor circuit corrosion from considering it is preferred as the alkali metal ion of foreign ion, alkaline-earth metal ions, halogen ion in use.
The amount of the thermosetting resins such as epoxy resin is preferably 10～80 quality % with respect to the photosensitive adhesive total amount, and considers from the viewpoint of photosensitive adhesive reliability, more preferably 20～60 quality %.If should amount surpass 80 quality %, then the viscosity of photosensitive adhesive uprises, and has the tendency that printing descends.On the other hand, if it then has the tendency that can't obtain sufficient hot pressing and high temperature bonding less than 10 quality %.The higher limit of thermosetting resin consumption and lower limit with respect to the photosensitive adhesive total amount, can be 10 quality %, 20 quality %, 33 quality %, 42.5 quality %, 60 quality % or 80 quality %.
As (A) thermosetting resin, its 5% thermal weight loss temperature is preferably more than 150 ℃, more preferably more than 180 ℃, and more preferably more than 200 ℃.Herein, 5% thermal weight loss temperature, be use differential thermogravimetric amount simultaneously determinator (SII nanosecond science and technology company system: TG/DTA6300), and at programming rate when to be that 10 ℃/min, nitrogen stream (400ml/min) are lower measure thermosetting resin, the temperature when its quality reduces 5%.By using the high thermosetting resin of 5% thermal weight loss temperature, can suppress thermosetting resin and when hot pressing or hot curing, volatilize.As having this stable on heating thermosetting resin, can enumerate the epoxy resin that has aromatic rings in the molecule, and consider from cementability, stable on heating viewpoint, particularly preferably use the glycidol ether of the glycidyl amine, bisphenol A-type (or AD type, S type, F type) of 3 functional-type (or 4 functional-type).
The photosensitive adhesive of present embodiment preferably contains hot curing initator (curing accelerator).As the hot curing initator, so long as promote the compound of epoxy resin cure or polymerization by heating, just be not particularly limited, for example, can enumerate phenol system compound, aliphatic amine, cycloaliphatic amines, aromatic polyamine, polyamide, aliphatic anhydride, alicyclic acid anhydrides, aromatic anhydride, dicyandiamide, organic acid dihydrazide, the boron trifluoride amine complex, imidazoles, cyanoguanidine derivative, the dicarboxyl acid dihydrazide, triphenyl phasphine, tetraphenylphosphoniphenolate tetraphenyl borate, 2-ethyl-4-methylimidazole-tetraphenyl borate, 2-[(3,5-dimethyl pyrazole base) carbonylamino] the ethyl-methyl acrylate, methacrylic acid 2-(0-[1 ' methyl propylidene is amino] carboxyamino) ethyl ester, 1,8-diazabicyclo [5,4,0] endecatylene-7-tetraphenyl borate and tertiary amine.Wherein, the dissolubility when never containing solvent, dispersed viewpoint are considered, preferably use imidazoles.The amount of hot curing initator with respect to the thermosetting resins such as epoxy resin 100 mass parts, is preferably 0.01～50 mass parts.In addition, consider from the viewpoint of cementability, thermal endurance, storage stability, also imidazoles particularly preferably.The higher limit of hot curing initiator amount and lower limit with respect to thermosetting resin 100 mass parts, can be 0.01 mass parts, 0.67 mass parts, 1 mass parts or 50 mass parts.
As imidazoles, its reaction beginning temperature can be for more than 50 ℃, more preferably more than 80 ℃, and most preferably are more than 100 ℃.If reaction beginning temperature less than 50 ℃, then because the storage stability of photosensitive adhesive descends, therefore has the viscosity rise of photosensitive adhesive, be difficult to control the tendency of thickness.
As imidazoles, preferably using average grain diameter is below the 10 μ m, more preferably below the 8 μ m, most preferably is the following compound of 5 μ m.By using the imidazoles of this average grain diameter, can suppress the variation of photosensitive adhesive viscosity, perhaps can suppress the sedimentation of imidazoles.In addition, when forming the film of photosensitive adhesive, reduced the concavo-convex of surface, thereby can obtain uniform film.Further owing to can carry out equably the curing of photosensitive adhesive when solidifying, therefore think can reduce degassed.In addition, by using the imidazoles to the dissolubility deficiency of epoxy resin, can obtain good storage stability.
As imidazoles, also can use the imidazoles that is dissolved in epoxy resin.By using this imidazoles, can further reduce the concave-convex surface when forming the photosensitive adhesive agent film.As this imidazoles, do not limit, can enumerate 2-ethyl-4-methylimidazole, 1-cyano ethyl-glyoxal ethyline, 1-cyano ethyl-2-ethyl-4-methylimidazole, 1-cyano ethyl-2-phenylimidazole, 1 benzyl 2 methyl imidazole, 1-benzyl-2-phenylimidazole etc.
Photosensitive adhesive can also contain phenol system compound as curing agent.As phenol system compound, more preferably has the phenol system compound of at least 2 above phenolic hydroxyl groups in the molecule.As this compound, for example, can enumerate phenol novolaks, cresols novolaks, tert-butyl phenol novolaks, bicyclopentadiene cresols novolaks, bicyclopentadiene phenol novolaks, xyxylene modified phenol novolaks, naphthols based compound, trisphenol based compound, four phenol novolaks, bisphenol-A phenolic varnish, poly-4-Vinyl phenol and phenol aralkyl resin.In these compounds, the compound of preferred number average molecular weight in 400～4000 scopes.Thus, when in the semiconductor device assembling process, heating, degassed in the time of can suppressing the heating as the pollution cause of semiconductor element or device etc.The amount of phenol system compound with respect to thermosetting resin 100 mass parts, is preferably 50～120 mass parts, more preferably 70～100 mass parts.
As (B) radioactive ray polymerizable compound; can enumerate the compound with ethene unsaturated group; as the ethene unsaturated group, can enumerate vinyl, pi-allyl, propargyl, cyclobutenyl, acetenyl, phenylene-ethynylene, dimaleoyl imino, Na Dike imide, (methyl) acryloyl group etc.And consider that from reactive view preferred (methyl) acryloyl group preferably contains simple function (methyl) acrylate.By adding simple function (methyl) acrylate, particularly can when be used for the exposure on B rank, reduce the crosslink density of photosensitive adhesive, and can make hot pressing, low stress and cementability after the exposure reach good state.
5% thermal weight loss temperature of simple function (methyl) acrylate is preferably more than 100 ℃, more preferably more than 120 ℃, more preferably more than 150 ℃, and most preferably is more than 180 ℃.Herein, 5% thermal weight loss temperature, to use simultaneously determinator (SII nanosecond science and technology company system: TG/DTA6300) of differential thermogravimetric amount, and when programming rate is 10 ℃/min, the lower mensuration of nitrogen stream (400ml/min) simple function (methyl) acrylate, the temperature when its quality reduces 5%.By using high simple function (methyl) acrylate of 5% thermal weight loss temperature, can suppress by exposure the B rankization after remaining unreacted simple function (methyl) acrylate when hot pressing or hot curing, volatilize.
So long as this simple function (methyl) acrylate, just be not particularly limited, it can use (methyl) acrylate that contains glycidyl, phenol EO modification (methyl) acrylate, phenol PO modification (methyl) acrylate, nonyl phenol EO modification (methyl) acrylate, nonyl phenol PO modification (methyl) acrylate, (methyl) acrylate that contains phenolic hydroxyl group, (methyl) acrylate that contains hydroxyl, fragrant family (methyl) acrylate such as phenyl phenol glycidol ether (methyl) acrylate and phenoxy group ethyl (methyl) acrylate, (methyl) acrylate that contains imide, (methyl) acrylate that contains carboxyl, (methyl) acrylate that contains isobornyl, contain (methyl) acrylate of dicyclopentadienyl and isobornyl (methyl) acrylate etc.
As simple function (methyl) acrylate, after the B rankization and by the cementability after the adaptation of sticky object, the curing, stable on heating viewpoint, consider, preferably have carbamate groups, isocyanurate group, imide or hydroxyl, and be particularly preferably simple function (methyl) acrylate that in molecule, has imide.
Can also preferably use simple function (methyl) acrylate with epoxy radicals.As the simple function with epoxy radicals (methyl) acrylate, consider from the viewpoint of storage stability, cementability, low degassed property, heat-resisting reliability and moisture-proof reliability, its 5% thermal weight loss temperature is preferably more than 150 ℃, more preferably more than 180 ℃, and most preferably is more than 200 ℃.As this simple function (methyl) acrylate with epoxy radicals, be not particularly limited, but by use 5% thermal weight loss temperature be polyfunctional epoxy resin more than 150 ℃ as raw material, can satisfy above-mentioned thermal endurance.
As the simple function with epoxy radicals (methyl) acrylate, be not particularly limited, except glycidyl methacrylate, glycidyl acrylate, 4-hydroxybutyl acrylate glycidol ether, 4-hydroxybutyl methacrylate glycidol ether, can also enumerate making functional group and the compound of ethene unsaturated group and the compound of polyfunctional epoxy resin reaction gained etc. that have with epoxy reaction.As above-mentioned and functional group epoxy reaction, be not particularly limited, can enumerate NCO, carboxyl, phenolic hydroxyl group, hydroxyl, acid anhydrides, amino, mercapto, amide groups etc.These compounds can use separately a kind, perhaps will be used in combination more than 2 kinds.
As the simple function with epoxy radicals (methyl) acrylate, for example, can be by in the presence of triphenyl phasphine, TBAB, make the polyfunctional epoxy resin that has at least 2 above epoxy radicals in 1 molecule, react with (methyl) acrylic acid that with respect to 1 equivalent epoxy radicals is 0.1～0.9 equivalent and obtain.In addition, by in the presence of the dibutyl tin laurate, make polyfunctional isocyanate's compound and the epoxy compounds reaction that contains (methyl) acrylate of hydroxyl and contain hydroxyl, perhaps make polyfunctional epoxy resin and (methyl) acrylate reactions that contains NCO, can obtain containing carbamate (methyl) acrylate of glycidyl etc.
Simple function (methyl) acrylate with epoxy radicals, from storage stability, cementability, low degassed property in the encapsulation after semiconductor device when heating assembling and the semiconductor device assembling, the viewpoint of thermal endurance and moisture-proof is considered, its 5% weight reduces temperature, the volatilization that causes at the heat drying that can suppress when forming adhesive film (photosensitive adhesive layer) or be preferably more than 150 ℃ to the surface segregation this point, the degassed hole that causes in the time can suppressing because of hot curing and peeling off, on the cementability decline this point more preferably more than 180 ℃, and more preferably more than 200 ℃, and most preferably be more than 260 ℃ can suppressing the hole that the unreacted component volatilization causes when refluxing and peel off this point.As this simple function (methyl) acrylate with epoxy radicals, be preferably the compound that has aromatic rings in the molecule.
Further, particularly chloride ion, water-disintegrable chlorine etc. are reduced to high-purity thing below the 1000ppm as simple function (methyl) acrylate with epoxy radicals, from preventing electromigration, preventing the viewpoint of metallic conductor circuit corrosion from considering it is preferred as the alkali metal ion of foreign ion, alkaline-earth metal ions, halogen ion in use.For example, the polyfunctional epoxy resin that has reduced alkali metal ion, alkaline-earth metal ions, halogen ion etc. by use can satisfy above-mentioned concentration impurity ion as raw material.Total chlorinity can be measured according to JISK7243-3.
As the simple function with epoxy radicals (methyl) the acrylate composition that satisfies above-mentioned thermal endurance and purity, be not particularly limited, can enumerate with bisphenol A-type (or AD type, the S type, the F type) glycidol ether, the glycidol ether of hydrogenated bisphenol A type, the glycidol ether of ethylene oxide adduct bisphenol-A and/or F type, the glycidol ether of propylene oxide adduct bisphenol-A and/or F type, the glycidol ether of phenol novolac resin, the glycidol ether of cresols novolac resin, the glycidol ether of bisphenol-A phenolic varnish gum, the glycidol ether of naphthalene resin, the glycidol ether of 3 functional-type (or 4 functional-type), the glycidol ether of bicyclopentadiene phenolic resins, the ethylene oxidic ester of dimeric dibasic acid, the glycidyl amine of 3 functional-type (or 4 functional-type) and the glycidyl amine of naphthalene resin etc. are as the material of raw material.
Particularly in order to improve hot pressing, low stress and cementability, the quantity of epoxy radicals and ethene unsaturated group is preferably respectively below 3, and particularly preferably the quantity of ethene unsaturated group is below 2.As this compound, be not particularly limited, but preferably use represented compound of following general formula (1), (2), (3), (4) or (5) etc.In following formula general formula (1)～(5), R 12And R 16Expression hydrogen atom or methyl, R 10, R 11, R 13And R 14The organic group of expression divalent, R 15, R 17And R 18Expression has the organic group of epoxy radicals or ethene unsaturated group.F represents integer.F for example is 1～10.
[changing 1]
Figure BDA00002806172400131
The amount of above-mentioned simple function (methyl) acrylate with respect to (B) radioactive ray polymerizable compound, is preferably 20～100 quality %, and more preferably 40～100 quality % most preferably are 50～100 quality %.Be above-mentioned amount by making simple function (methyl) acrylate, can improve after the B rankization with by the adaptation of sticky object and hot pressing.
As (B) radioactive ray polymerizable compound, can also contain 2 officials can above (methyl) acrylate.As this acrylate, be not particularly limited, can enumerate diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, the diethylene glycol dimethylacrylate, TEGDMA, the TEG dimethylacrylate, trimethylolpropane diacrylate, trimethylolpropane triacrylate, the trimethylolpropane dimethylacrylate, trimethylol-propane trimethacrylate, 1, the 4-butanediol diacrylate, 1, the 6-hexanediyl ester, 1, the 4-butanediol dimethylacrylate, 1, the 6-hexanediol dimethacrylate, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, pentaerythritol acrylate trimethyl, pentaerythritol tetramethylacrylate, dipentaerythritol acrylate, dipentaerythritol hexamethyl acrylate, styrene, divinylbenzene, the 4-vinyltoluene, 4-vinylpridine, NVP, acrylic acid 2-hydroxy methacrylate, 2-hydroxyethyl methacrylate, 1,3-acryloxy-2-hydroxy propane, 1,2-methacryloxy-2-hydroxy propane, methylene-bisacrylamide, N,N-DMAA, N hydroxymethyl acrylamide, the triacrylate of three (beta-hydroxy ethyl) isocyanuric acid ester, the represented compound of following general formula (6), urethane acrylate, carbamate methacrylate and urea acrylate etc.
[changing 2]
In the above-mentioned general formula (6), R 19And R 20Represent independently of one another hydrogen atom or methyl, g and h represent 1～20 integer independently of one another.
These radioactive ray polymerizable compounds can use separately a kind or will be used in combination more than 2 kinds.Wherein, from can fully giving the solvent resistance after the curing, and viscosity is low, and the viewpoint with high 5% thermal weight loss temperature is considered the radioactive ray polymerizable compound with two ol skeletons that preferred above-mentioned general formula (6) is represented.
By using the high radioactive ray polymerizable compound of functional group's equivalent, can more effectively suppress to be applied to stress (low stress) on the semiconductor wafer and the warpage (low warpage) of semiconductor wafer.The radioactive ray polymerizable compound that functional group's equivalent is high, its polymer functional group's equivalent is preferably more than the 200eq/g, more preferably more than the 300eq/g, most preferably is more than the 400eq/g.By using polymer functional group's equivalent to be the radioactive ray polymerizable compound with ether skeleton, carbamate groups and/or isocyanurate group more than the 200eq/g, can improve photosensitive adhesive cementability and can low stress, low warpage.And can be that radioactive ray polymerizable compound more than the 200eq/g and polymer functional group's equivalent are less than the radioactive ray polymerizable compound of 200eq/g and use with polymer functional group's equivalent.
(B) amount of radioactive ray polymerizable compound with respect to the photosensitive adhesive total amount, is preferably 10～95 quality %, and the viewpoint of wetting and spreading is considered during from chip pressing, more preferably 20～90 quality % consider from the viewpoint that the rear shape of B rankization keeps, and most preferably are 40～90 quality %.If (B) composition is less than 10 quality %, then there is the viscous force behind the B rank to become large tendency, and if surpass 95 quality %, the tendency that then has the adhesive strength after the hot curing to descend.Higher limit and the lower limit of radioactive ray polymerizable compound consumption with respect to the photosensitive adhesive total amount, can be 10 quality %, 20 quality %, 40 quality %, 56.7 quality %, 66 quality %, 90 quality % or 95 quality %.
(B) the radioactive ray polymerizable compound is preferably lower to aqueous in room temperature (15 ℃～30 ℃), if consider the detachment of photosensitive adhesive on the mesh galley, then its viscosity is preferably below the 5000mPas, if and further consider by flowing voluntarily and planarization after the printing, then more preferably below the 3000mPas.If viscosity surpasses 5000mPas, then the viscosity rise of photosensitive adhesive has the tendency that printing descends.
As (B) radioactive ray polymerizable compound, its 5% thermal weight loss temperature is preferably more than 120 ℃, more preferably more than 150 ℃, and more preferably more than 180 ℃.Herein, 5% thermal weight loss temperature, be use differential thermogravimetric amount simultaneously determinator (SII nanosecond science and technology company system: TG/DTA6300), and at programming rate when to be that 10 ℃/min, nitrogen stream (400ml/min) are lower measure the radioactive ray polymerizable compound, the temperature when its quality reduces 5%.By using the high radioactive ray polymerizable compound of 5% thermal weight loss temperature, can suppress unreacted radioactive ray polymerizable compound and when hot pressing or hot curing, volatilize.
As (C) Photoepolymerizationinitiater initiater (light trigger), consider from the viewpoint that improves the photopolymerization sensitivity, be that the molecule absorptivity of the light of 365nm is the material more than the 100ml/gcm for wavelength preferably, and the above material of 200ml/gcm more preferably.In addition, the molecule absorptivity can be passed through 0.001 quality % acetonitrile solution of modulation sample, and uses spectrophotometer (high new company of Hitachi system, " U-3310 " (trade name)) that this measured in solution absorbance is obtained.
As this (C) composition; for example can enumerate 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-the 1-butanone; 2; 2-dimethoxy-1; 2-diphenylethane-1-ketone; 1-hydroxyl-cyclohexyl-phenyl-ketone; 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholino propane-1-ketone; 2; the 4-diethyl thioxanthone; the aromatic ketones such as 2-EAQ and phenanthrenequione; the dibenzoyl derivatives such as dibenzoyl dimethyl acetal; the 2-(Chloro-O-Phenyl)-4; 5-diphenyl-imidazole dimer; the 2-(Chloro-O-Phenyl)-4; 5-two (m-methoxyphenyl) imidazole dimer; the adjacent fluorophenyl of 2-()-4; 5-phenylimidazole dimer; the 2-(o-methoxyphenyl)-4; 5-diphenyl-imidazole dimer; the 2-(p-methoxyphenyl)-4; 5-diphenyl-imidazole dimer; 2; 4-two (p-methoxyphenyl)-5-phenylimidazole dimer and 2-(2; the 4-Dimethoxyphenyl)-4; 5-diphenyl-imidazole dimer etc. 2; 4; 5-triarylimidazoles dimer; 9-phenylacridine and 1; 7-two (9; 9 '-acridinyl) acridine derivatives such as heptane; two (2; 6-dimethoxy benzoyl)-2; 4; 4-trimethyl-amyl group phosphine oxide and two (2; 4; the 6-trimethylbenzoyl)-two acylphosphine oxide such as phenylphosphine oxide, and the compound etc. with maleimide.These compounds can use separately a kind or will be used in combination more than 2 kinds.
In above-mentioned Photoepolymerizationinitiater initiater, consider from the deliquescent viewpoint the photosensitive adhesive that does not contain solvent, can preferably use 2,2-dimethoxy-1,2-diphenylethane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-1-butanone, 2,2-dimethoxy-1,2-diphenylethane-1-ketone and 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholino propane-1-ketone.In addition, even from air atmosphere, also can the viewpoint on photosensitive adhesive layer B rank be considered by exposure, can preferably use 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-1-butanone, 2,2-dimethoxy-1,2-diphenylethane-1-ketone and 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholino propane-1-ketone.
(C) composition also can contain the light trigger that irradiation by radioactive ray shows the function of the polymerization that promotes epoxy resin and/or reaction.As this light trigger, for example, can enumerate the light alkali generation agent, acidic smooth acid producing agent etc., particularly preferably the light alkali generation agent by radiation exposure that produce alkali by radiation exposure.
Produce agent by making with light alkali, can further improve photosensitive adhesive for by cementability (high temperature bonding) and the moisture-proof of sticky object when the high temperature.As its reason, can enumerate by light alkali and produce the effective curing catalysts as epoxy resin of alkali that agent generates, therefore can further improve crosslink density, the curing catalysts that perhaps generates is few to the corrosion of substrate etc.Contain light alkali in the photosensitive adhesive and produce agent by making, can improve crosslink density, and degassed can more reduce high temperature and place the time.Further, can think that it can make temperature low temperature and the short time of curing process.
Light alkali produces agent, so long as produce the compound of alkali when the irradiation radioactive ray, just can use with being not particularly limited.As the alkali that produces, consider preferred strongly alkaline compound from viewpoint reactive, curing rate.
The alkali that produces during as this irradiation radioactive ray, for example, can enumerate imidazoles, 2, the imdazole derivatives such as 4-methylimidazole and 1-methylimidazole, piperazine and 2, the bridged piperazine derivatives such as 5-lupetazin, piperidines and 1, the piperidine derivatives such as 2-lupetidine, proline derivative, trimethylamine, the trialkylamine such as triethylamine and triethanolamine derivative, 4-methylamino pyridine and 4-dimethylaminopyridine etc. are at 4 pyridine derivates that carry out amino or alkyl amino replacement, the pyrrolidin derivatives such as pyrrolidines and positive crassitude, the dihydro pyridine derivate, triethylenediamine and 1,8-diazabicyclo (5,4,0) 11 carbon-ester ring type amine derivatives such as 1-alkene (DBU), and benzyl methyl amine, the benzyl amine derivatives such as benzyl dimethyl amine and benzyl diethylamide.
Produce agent as the light alkali that produces above-mentioned alkali by radiation exposure, for example, can use Journal of Photopolymer Science and Technology12 volume, 313～314 (1999) or Chemistry of Materials11 volume, the quaternary ammonium salt derivative that 170～176 (1999) etc. are put down in writing.These light alkali produce agent, owing to producing alkaline trialkylamine by the irradiation of active ray (radioactive ray), therefore are best suited for the curing of epoxy resin.
Produce agent as light alkali, can also use Journal of American Chemical Society118 to roll up the carbamic acid derivative that 12925 pages (1996) or Polymer Journal28 volume 795 pages (1996) etc. are put down in writing.
The light alkali that produces alkali as the irradiation by active ray produces agent; can use 2; 4-dimethoxy-1; 2-diphenylethane-1-ketone; 1; the 2-acetyl caproyl; 1-[4-(phenyl sulfenyl)-2-(o-benzoyl oxime)]; ethyl ketone; 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-1-(o-acetyl oxime) etc. 9 oxime derivate; the 2-benzyl of selling as optical free radical generation agent-2-dimethylamino-1-(4-morpholino phenyl)-the 1-butanone; 2; 2-dimethoxy-1,2-diphenylethane-1-ketone; 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholino propane-1-ketone; 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-the 1-butanone; the hexa-aryl bi-imidazole derivative (can replace on phenyl halogen is arranged; alkoxyl; nitro; the substituting groups such as cyano group); and benzisoxa
Figure BDA00002806172400171
Trazodone derivative etc.
Produce agent as light alkali, can also use at high molecular main chain and/or side chain and import the compound that produces the group of alkali.As molecular weight in this case, from considering as the cementability of photosensitive adhesive, flowability and stable on heating viewpoint, weight average molecular weight is preferably 1000～100000, and more preferably 5000～30000.
Above-mentioned smooth alkali produces agent, owing to can not show the reactivity with epoxy resin under unexposed state, therefore at room temperature storage stability is very excellent.
The amount of Photoepolymerizationinitiater initiater, with respect to radioactive ray polymerizable compound 100 mass parts, can be for more than 5 mass parts or more than 1 mass parts.The amount of Photoepolymerizationinitiater initiater, with respect to radioactive ray polymerizable compound 100 mass parts, can be for below 0.1 mass parts or below 1 mass parts.
The photosensitive adhesive of present embodiment can as required and be used sensitizer.As this sensitizer, for example, can enumerate camphorquinone, dibenzoyl, biacetyl, the dibenzoyl dimethyl acetal, the dibenzoyl diethyl acetal, dibenzoyl contracting two (2-methyl cellosolves), 4,4 '-dimethyl diphenyl acyl dimethyl acetal, anthraquinone, the 1-chloroanthraquinone, the 2-chloroanthraquinone, 1,2-benzo anthraquinone, the 1-hydroxy-anthraquione, the 1-methylanthracene quinone, the 2-EAQ, the 1-bromo anthraquinone, thioxanthones, ITX, 2-nitro thioxanthones, 2-methyl thioxanthones, 2,4-dimethyl thioxanthones, 2, the 4-diethyl thioxanthone, 2,4-diisopropyl thioxanthones, 2-chloro-7-trifluoromethylthioxanthone, thioxanthones-10, the 10-dioxide, thioxanthones-10-oxide, the benzoin methyl ether, the benzoin ether, isopropyl ether, the benzoin isobutyl ether, benzophenone, two (4-dimethylaminophenyl) ketone, 4,4 '-two diethylamino benzophenone and the compound that contains azido.These compounds can be used alone or with two or more.
In the photosensitive adhesive of present embodiment, from improve low stress, with considered by the viewpoint of the adaptation of sticky object, hot pressing, can also contain (D) thermoplastic resin.(D) vitrification point of composition (Tg) is preferably below 150 ℃, more preferably below 120 ℃, more preferably below 100 ℃, most preferably is below 80 ℃.When this Tg surpasses 150 ℃, have the tendency of the viscosity rise of photosensitive adhesive.In addition, the high temperature needing with by the sticky object hot pressing time more than 150 ℃ has the tendency that semiconductor wafer easily produces warpage.
Herein, " Tg " is expressed as the main peak temperature that disperses of membranization (D) composition.Use the viscoelasticity analysis device " RSA-2 " (trade (brand) name) of Rheometric company system, be that 100 μ m, programming rate are that 5 ℃/min, frequency are 1Hz, measure temperature and measure under-150～300 ℃ the condition at thickness, near the tan δ peak temperature that at this moment observes Tg is main dispersion temperature.
(D) weight average molecular weight of composition preferably is controlled in 5000～500000 the scope, and can make hot pressing and high temperature bonding height and deposit on this point more preferably 10000～300000.Herein, " weight average molecular weight " refers to use the high performance liquid chromatograph " C-R4A " (trade name) of company of Shimadzu Seisakusho Ltd. system, the weight average molecular weight when measuring with polystyrene conversion.
As (D) composition, except mylar, polyether resin, polyimide resin, polyamide, polyamide-imide resin, polyetherimide resin, polyurethane resin, imide-urethane resin, polyurethane amide imide resin, siloxanes polyimide resin, polyesterimide resin, their copolymer, their precursor (polyamic acid etc.), can also enumerate polyphenyl also
Figure BDA00002806172400181
Azoles resin, phenoxy resin, polysulfone resin, polyethersulfone resin, polyphenylene sulfide, mylar, polyether resin, polycarbonate resin, polyether ketone resin, weight average molecular weight are 10,000～1,000,000 (methyl) acrylic copolymer, novolac resin and phenolic resins etc.These resins can use separately a kind or will be used in combination more than 2 kinds.In addition, can also on the main chain and/or side chain of these resins, give glycol-based, carboxyl and/or the hydroxyls such as ethylene glycol and propylene glycol.
Wherein, consider from high temperature bonding, stable on heating viewpoint, (D) composition is preferably the resin with imide.As the resin with imide, for example, can enumerate polyimide resin, polyamide-imide resin, polyetherimide resin, imide-urethane resin, polyurethane amide imide resin, siloxanes polyimide resin, polyesterimide resin and their copolymer, for example, polyimide resin can adopt known method to make tetracarboxylic dianhydride and diamines carry out condensation reaction and obtain.That is to say, in organic solvent, make tetracarboxylic dianhydride and diamines with etc. the mole, or as required with respect to tetracarboxylic dianhydride's total 1.0mol make the preferred 0.5～2.0mol of total of diamines, more preferably the scope of 0.8～1.0mol is adjusted ratio of components (the interpolation order of each composition arbitrarily), in reaction temperature below 80 ℃, carry out addition reaction under preferred 0～60 ℃.Along with the carrying out of reaction, the viscosity of reactant liquor slowly rises, and generates the polyamic acid as polyimide resin precursor.In addition, in order to suppress the decline of each characteristic of photosensitive adhesive, above-mentioned tetracarboxylic dianhydride is preferably with acetic anhydride and carries out tetracarboxylic dianhydride after recrystallizing and refining is processed.
Ratio of components for tetracarboxylic dianhydride and diamines in the above-mentioned condensation reaction, if the total 1.0mol with respect to the tetracarboxylic dianhydride, the total of diamines surpasses 2.0mol, then in the rewarding polyimide resin, has the many tendencies of quantitative change of the polyimide oligomers of amine end.Also have in addition the weight average molecular weight of polyimide resin to reduce, photosensitive adhesive comprises the tendency of the various characteristics deficiency of thermal endurance.On the other hand, if with respect to tetracarboxylic dianhydride's total 1.0mol, the total of diamines then has the many tendencies of quantitative change of the polyimide resin oligomer with acid terminal (carboxyl terminal) less than 0.5mol.Also have in addition the weight average molecular weight of polyimide resin to reduce, photosensitive adhesive comprises the tendency of the various characteristics deficiency of thermal endurance.
Polyimide resin can obtain by making above-mentioned reactant (polyamic acid) dehydration closed-loop.Dehydration closed-loop can be undertaken by the hot closed loop method of carrying out heat treated, the chemical closed loop method of using dehydrating agent etc.
Be not particularly limited as the tetracarboxylic dianhydride who can be used as the polyimide resin raw material, for example, can enumerate pyromellitic acid dianhydride, 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, 2,2 ', 3,3 '-biphenyl tetracarboxylic dianhydride, 2,2-two (3,4-dicarboxyl phenyl) propane dianhydride, two (2,3-dicarboxyl phenyl) the propane dianhydrides of 2,2-, 1,1-two (2,3-dicarboxyl phenyl) ethane dianhydride, two (3,4-dicarboxyl phenyl) the ethane dianhydrides of 1,1-, two (2,3-dicarboxyl phenyl) methane dianhydride, two (3,4-dicarboxyl phenyl) methane dianhydride, two (3,4-dicarboxyl phenyl) sulfone dianhydride, 3,4,9, the 10-perylenetetracarboxylic dianhydride, two (3,4-dicarboxyl phenyl) ether dianhydride, benzene-1,2,3, the 4-tetracarboxylic dianhydride, 3,4,3 ', 4 '-benzophenone tetracarboxylic dianhydride, 2,3,2 ', 3 '-benzophenone tetracarboxylic dianhydride, 3,3,3 ', 4 '-benzophenone tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic acid dianhydride, Isosorbide-5-Nitrae, 5,8-naphthalene tetracarboxylic acid dianhydride, 2,3,6,7-naphthalene tetracarboxylic acid dianhydride, 1,2,4,5-naphthalene tetracarboxylic acid dianhydride, 2,6-dichloronaphtalene-1,4,5,8-tetracarboxylic dianhydride, 2,7-dichloronaphtalene-1,4,5,8-tetracarboxylic dianhydride, 2,3,6,7-Tetrachloronaphthalene-Isosorbide-5-Nitrae, 5, the 8-tetracarboxylic dianhydride, luxuriant and rich with fragrance-1,8,9,10-tetracarboxylic dianhydride, pyrazine-2,3,5,6-tetracarboxylic dianhydride, thiophene-2,3,5, the 6-tetracarboxylic dianhydride, 2,3,3 ', 4 '-biphenyl tetracarboxylic dianhydride, 3,4,3 ', 4 '-biphenyl tetracarboxylic dianhydride, 2,3,2 ', 3 '-biphenyl tetracarboxylic dianhydride, two (3,4-dicarboxyl phenyl) dimethylsilane dianhydride, two (3,4-dicarboxyl phenyl) aminomethyl phenyl silane dianhydride, two (3,4-dicarboxyl phenyl) diphenyl silane dianhydride, Isosorbide-5-Nitrae-two (3,4-dicarboxyl phenyl dimetylsilyl) benzene dianhydride, 1,3-two (3,4-dicarboxyl phenyl)-1,1,3,3-tetramethyl bicyclohexane dianhydride, TOPOT 2,2′ p phenylenebis (trimellitate acid anhydride), the ethylidene tetracarboxylic dianhydride, 1,2,3,4-butane tetracarboxylic acid dianhydride, decahydronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydro naphthalene-1,2,5,6-tetracarboxylic dianhydride, pentamethylene-1,2,3,4-tetracarboxylic dianhydride, pyrrolidines-2,3,4, the 5-tetracarboxylic dianhydride, 1,2,3,4-cyclobutane tetracarboxylic dianhydride, two (outer formula-two rings [2,2,1] heptane-2, the 3-dicarboxylic acid dianhydride, two rings-[2,2,2]-and Xin-7-alkene-2,3,5, the 6-tetracarboxylic dianhydride, 2, two (3,4-dicarboxyl phenyl) the propane dianhydrides of 2-, two [the 4-(3 of 2,2-, 4-dicarboxyl phenyl) phenyl] the propane dianhydride, 2, two (3, the 4-dicarboxyl phenyl) hexafluoropropane dianhydrides of 2-, two [the 4-(3 of 2,2-, 4-dicarboxyl phenyl) phenyl] hexafluoropropane dianhydride, 4,4 '-two (3,4-di carboxyl phenyloxy) diphenylsulfide dianhydride, Isosorbide-5-Nitrae-two (2-hydroxyl hexafluoro isopropyl) benzene two (trimellitic anhydride), 1, two (2-hydroxyl hexafluoro isopropyl) benzene of 3-two (trimellitic anhydride), 5-(2,5-dioxy tetrahydrofuran base)-and 3-methyl-3-cyclohexene-1, the 2-dicarboxylic acid dianhydride, oxolane-2,3, the tetracarboxylic dianhydride that 4,5-tetracarboxylic dianhydride and following general formula (7) are represented etc.In the following general formula (7), a represents 2～20 integer.
[changing 3]
Figure BDA00002806172400201
The represented tetracarboxylic dianhydride of above-mentioned general formula (7) for example, can be synthesized by trimellitic anhydride monochloro compound and corresponding glycol.Specifically, can enumerate 1, the 2-(ethylidene) two (trimellitic anhydride), 1, the 3-(trimethylene) two (trimellitic anhydride), 1, the 4-(tetramethylene) two (trimellitic anhydride), 1, the 5-(pentamethylene) two (trimellitic anhydride), 1, the 6-(hexa-methylene) two (trimellitic anhydride), 1, the 7-(heptamethylene) two (trimellitic anhydride), 1,8-(eight methylene) two (trimellitic anhydrides), 1,9-(nine methylene) two (trimellitic anhydrides), 1, the 10-(decamethylene) two (trimellitic anhydride), 1,12-(ten dimethylenes) two (trimellitic anhydrides), 1,16-(, ten hexa-methylenes) two (trimellitic anhydrides), 1,18-(, 18 methylene) two (trimellitic anhydrides).
As the tetracarboxylic dianhydride, consider preferred following general formula (8) or (9) represented tetracarboxylic dianhydride from giving to the good solubility of solvent and moisture-proof and to the viewpoint of the transparency of the light of wavelength 365nm.
[changing 4]
Figure BDA00002806172400211
Above-described tetracarboxylic dianhydride can use separately a kind or will be used in combination more than 2 kinds.
(D) composition is further considered from the viewpoint that improves adhesive strength, can also use the polyimide resin that contains carboxyl and/or phenolic hydroxyl group.Can as the diamines of the raw material of the above-mentioned polyimide resin that contains carboxyl and/or hydroxyl, preferably comprise following general formula (10), (11), (12) or (13) represented aromatic diamine.
[changing 5]
As being not particularly limited as other diamines of above-mentioned polyimide resin raw material, for example, can enumerate o-phenylenediamine, m-phenylene diamine (MPD), p-phenylenediamine (PPD), 3,3 '-diamino-diphenyl ether, 3,4 '-diamino-diphenyl ether, 4,4 '-diamino-diphenyl ether, 3,3 '-diaminodiphenyl-methane, 3,4 '-diaminodiphenyl-methane, 4,4 '-diaminodiphenyl-methane, it is two that (4-amino-3, the 5-3,5-dimethylphenyl) methane, it is two that (4-amino-3, the 5-diisopropyl phenyl) methane, 3,3 '-diamino-diphenyl difluoromethane, 3,4 '-diamino-diphenyl difluoromethane, 4,4 '-diamino-diphenyl difluoromethane, 3,3 '-diamino diphenyl sulfone, 3,4 '-diamino diphenyl sulfone, 4,4 '-diamino diphenyl sulfone, 3,3 '-diamino-diphenyl thioether, 3,4 '-diamino-diphenyl thioether, 4,4 '-diamino-diphenyl thioether, 3,3 '-diamino-diphenyl ketone, 3,4 '-diamino-diphenyl ketone, 4,4 '-diamino-diphenyl ketone, 2, two (3-aminophenyl) propane of 2-, 2,2 '-two (3,4 '-diamino-diphenyl) propane, 2, two (4-aminophenyl) propane of 2-, 2, two (3-aminophenyl) HFC-236fa of 2-, 2,2-(3,4 '-diamino-diphenyl) HFC-236fa, 2, two (4-aminophenyl) HFC-236fa of 2-, 1, two (3-amino-benzene oxygen) benzene of 3-, 1, two (3-amino-benzene oxygen) benzene of 4-, 1, two (4-amino-benzene oxygen) benzene of 4-, 3,3 '-(1, two (the 1-methyl ethylidene) dianils of 4-phenylene, 3,4 '-(1, two (the 1-methyl ethylidene) dianils of 4-phenylene, 4,4 '-(1, two (the 1-methyl ethylidene) dianils of 4-phenylene, 2, two (4-(3-amino-benzene oxygen) phenyl of 2-) propane, 2, two (4-(3-amino-benzene oxygen) phenyl of 2-) HFC-236fa, 2, two (4-(4-amino-benzene oxygen) phenyl of 2-) HFC-236fa, two (4-(3-amino ethoxy) phenyl) thioether, two (4-(4-amino ethoxy) phenyl) thioether, two (4-(3-amino ethoxy) phenyl) sulfone, two (4-(4-amino ethoxy) phenyl) sulfone, 3,3 '-dihydroxy-4,4 '-benzidine and 3, the aromatic diamines such as 5-diaminobenzoic acid, 1, two (amino methyl) cyclohexanes of 3-, two (the 4-amino-benzene oxygen phenyl) propane of 2,2-, the fatty ether diamines that following general formula (14) is represented, and the represented siloxane diamine of following general formula (15).
In the above-mentioned diamines, consider from giving with the viewpoint of the compatibility of other composition, the fatty ether diamines that preferred following general formula (14) is represented, more preferably ethylene glycol and/or propylene glycol are diamines.In the following general formula (14), R 1, R 2And R 3Represent that independently of one another carbon number is 1～10 alkylidene, b represents 2～80 integer.
[changing 6]
As this fatty ether diamines, specifically, can enumerate Sun-Techno Chemical(strain) aliphatic diamines such as polyoxy alkylidene diamines of polyetheramine D-230, the D-400 of Jeffamine D-230, D-400, D-2000, the D-4000 of system, ED-600, ED-900, ED-2000, EDR-148, BASF (system) and D-2000 etc.These diamines are preferably more than 20 % by mole of whole diamines, and consider from making with the compatibility of other gradation compositions such as (A) thermosetting resin, (B) radioactive ray polymerizable compound and hot pressing and high temperature bonding height and the viewpoint of depositing, more preferably more than 50 % by mole.
As above-mentioned diamines, giving on adaptation under the room temperature, the cementability this point the represented siloxane diamine of preferred following general formula (15).In the following general formula (15), R 4And R 9Represent that independently of one another carbon number is that 1～5 alkylidene maybe can have substituent phenylene, R 5, R 6, R 7And R 8Represent that independently of one another carbon number is 1～5 alkyl, phenyl or phenoxy group, d represents 1～5 integer.
[changing 7]
Figure BDA00002806172400241
These diamines are preferably 0.5～80 % by mole of whole diamines, and consider more preferably 1～50 % by mole from the viewpoint that can make hot pressing and high temperature bonding height and deposit.If it is lower than 0.5 % by mole, the effect of then adding siloxane diamine diminishes, and if it surpasses 80 % by mole, then have and the compatibility of other composition, the tendency of high temperature bonding decline.
As the represented siloxane diamine of above-mentioned general formula (15), specifically, be 1 material as d in the formula (15), can enumerate 1,1,3,3-tetramethyl-1, two (4-aminophenyl) disiloxane of 3-, 1,1,3,3-, four phenoxy groups-1, two (4-amino-ethyl) disiloxane of 3-, 1,1,3,3-tetraphenyl-1, two (2-amino-ethyl) disiloxane of 3-, 1,1,3,3-tetraphenyl-1, two (3-aminopropyl) disiloxane of 3-, 1,1,3,3-tetramethyl-1, two (2-amino-ethyl) disiloxane of 3-, 1,1,3,3-tetramethyl-1, two (3-aminopropyl) disiloxane of 3-, 1,1,3,3-tetramethyl-1, two (3-aminobutyl) disiloxane of 3-and 1,3-dimethyl-1,3-dimethoxy-1, two (4-aminobutyl) disiloxane of 3-etc.Be 2 material as d in the formula (15), can enumerate 1,1,3,3,5, the 5-vegolysen, two (4-aminophenyl) trisiloxanes of 5-, 1,1,5,5-tetraphenyl-3,3-dimethyl-1, two (3-aminopropyl) trisiloxanes of 5-, 1,1,5,5-tetraphenyl-3,3-dimethoxy-1, two (4-aminobutyl) trisiloxanes of 5-, 1,1,5,5-tetraphenyl-3,3-dimethoxy-1,5-two (the amino amyl group of 5-) trisiloxanes, 1,1,5,5-tetramethyl-3,3-dimethoxy-1, two (2-amino-ethyl) trisiloxanes of 5-, 1,1,5,5-tetramethyl-3,3-dimethoxy-1, two (4-aminobutyl) trisiloxanes of 5-, 1,1,5,5-tetramethyl-3,3-dimethoxy-1,5-two (the amino amyl group of 5-) trisiloxanes, 1,1,3,3,5, the 5-vegolysen, two (3-aminopropyl) trisiloxanes of 5-, 1,1,3,3,5,5-Hexaethyl-1, two (3-aminopropyl) trisiloxanes and 1,1 of 5-, 3,3,5,5-, six propyl group-1, two (3-aminopropyl) trisiloxanes of 5-etc.
Above-mentioned diamines can use separately a kind or will be used in combination more than 2 kinds.
Above-mentioned polyimide resin can use separately a kind or as required will be more than 2 kinds mix (blend) and use.
As mentioned above, when determining the composition of polyimide resin, the Tg that is preferably designed for polyimide resin is below 150 ℃, and as the diamines of polyimide resin raw material, particularly preferably uses the represented fatty ether diamines of above-mentioned general formula (14).
When synthetic above-mentioned polyimide resin, by following general formula (16), (17) or (18) represented such simple function acid anhydrides and/or monofunctional amines of compound are put in the condensation reaction solution, can import acid anhydrides or diamines functional group in addition in polymer ends.And, can reduce thus the molecular weight of polymer, and the viscosity that reduces photosensitive adhesive, hot pressing improved.
[changing 8]
Figure BDA00002806172400251
(D) composition can also contain imidazoles etc. have promote the epoxy resin cure function functional group as its main chain and/or side chain.For example, containing the polyimides of imidazoles can be as described below and obtain.Can obtain as two amine components shown in above-mentioned by using the represented diamines that contains imidazole radicals of a part of following structural formula.
[changing 9]
Figure BDA00002806172400252
Above-mentioned polyimide resin, consider from the viewpoint that can carry out equably the B rank, transmitance to the light of wavelength 365nm when thickness is shaped to 30 μ m is preferably more than 10%, and from can considering with the viewpoint that lower exposure be carried out the B rank, more preferably more than 20%.This polyimide resin for example, can synthesize by making the represented siloxane diamine reaction of the represented fatty ether diamines of the represented acid anhydrides of above-mentioned general formula (7) and above-mentioned general formula (14) and/or above-mentioned general formula (15).
As (D) thermoplastic resin, from suppressing viscosity rise, further the viewpoint of the dissolving remnants of attenuating in photosensitive adhesive is considered, preferably using lower at normal temperature (25 ℃) is aqueous aqueous thermoplastic resin.This thermoplastic resin does not use solvent, and can react by heating, so this photosensitive adhesive that does not use solvent of present embodiment is being cut down the operation of desolventizing, reduces remaining solvent, cut down that to precipitate aspect the operation be effective again.In addition, aqueous thermoplastic resin also easily takes out from reacting furnace.As this aqueous thermoplastic resin, be not particularly limited, can enumerate rubber-like polymer, polyolefin, acrylate copolymer, organosilicon polymer, polyurethane, polyimides and the polyamidoimides etc. such as polybutadiene, acrylonitrile-butadiene oligomer, polyisoprene and polybutene.Wherein, can preferably use polyimide resin.
As aqueous polyimide resin, for example, can obtain by making above-mentioned acid anhydrides and fatty ether diamines, siloxane diamine reaction.As synthetic method, can be by not adding solvent, and acid anhydrides is dispersed in fatty ether diamines, the siloxane diamine, and heat and obtain.
Photosensitive adhesive in the present embodiment, be preferably that (ORC makes made using the parallel exposure machine of high accuracy, " EXM-1172-B-∞ " (trade name)) exposure after, the lowest melt viscosity under 20 ℃～300 ℃ is the photosensitive adhesive below the 30000Pas.Also can use parallel exposing machine (the fine jade Mi Nasi of Co., Ltd. makes, " ML-210FM mask aligner " (trade name)) to replace the above-mentioned parallel exposure machine of high accuracy.
In this manual, determination of viscoelasticity device ARES(Rheometrics Scientific FE company system is used in " lowest melt viscosity " expression), to being 1000mJ/cm by light quantity 2Light exposure after sample when measuring, the minimum of the melt viscosity under 20 ℃～300 ℃.In addition, assay plate is used the parallel-plate of diameter 8mm.Condition determination is that programming rate is 5 ℃/min, and measuring temperature is 20 ℃～300 ℃, and frequency is 1Hz.
Above-mentioned lowest melt viscosity is preferably below the 20000Pas, more preferably below the 18000Pas, and more preferably below the 15000Pas.By having the lowest melt viscosity in the above-mentioned scope, can guarantee enough Low Temperature Thermal pressings, even also can give good adaptation for irregular substrate of tool etc.The lower limit of above-mentioned lowest melt viscosity is special the setting not, but considers from aspects such as operability, wishes for more than the 10Pas.
Photosensitive adhesive in the present embodiment can use hot radical to produce agent as required.Produce agent as hot radical, be preferably organic peroxide.As organic peroxide, be preferably 1 minute half life temperature and be the material more than 80 ℃, the material more than 100 ℃ more preferably, and most preferably be material more than 120 ℃.Organic peroxide can be considered the modulation condition, masking temperature, curing (applying) condition, other process conditions, storage stability etc. of photosensitive adhesive and selects.As operable organic peroxide, be not particularly limited, for example, can enumerate 2,5-dimethyl-2,5-two (tert-butyl hydroperoxide hexane), cumyl peroxide, tert-butyl hydroperoxide-2 ethyl hexanoic acid ester, uncle's hexyl peroxidating-2 ethyl hexanoic acid ester, 1, two (tert-butyl hydroperoxide)-3 of 1-, 3,5-trimethyl-cyclohexane, two (peroxidating of uncle's hexyl)-3 of 1,1-, 3,5-trimethyl-cyclohexane and two (4-tert-butylcyclohexyl) peroxy dicarbonate etc. wherein, can use separately a kind or will be more than 2 kinds mix and use.By containing organic peroxide, can make the rear remaining unreacted radioactive ray polymerizable compound reaction of exposure, and can reduce degassed (low degassedization), realize high bondingization.
Hot radical produces the amount of agent, with respect to the total amount of radioactive ray polymerizable compound, is preferably 0.01～20 quality %, 0.1～10 quality % more preferably, and most preferably be 0.5～5 quality %.If less than 0.01 quality %, then curing property decline, additive effect diminishes, and if above 5 quality %, the amount of gas evolved increase is arranged then, the tendency that storage stability descends.
Produce agent as hot radical, so long as 1 minute half life temperature is the compound more than 80 ℃, just be not particularly limited, for example, can enumerate Perhexa25B(day oil company system), 2,5-dimethyl-2,5-two (tert-butyl hydroperoxide hexane) (1 minute half life temperature: 180 ℃), Percumyl D(day oil company system) and cumyl peroxide (1 minute half life temperature: 175 ℃) etc.
In the photosensitive adhesive of present embodiment, in order to give storage stability, flexibility (adaptability) of operation or non-oxidizability, can also in the scope of not damaging photosensitive adhesive curing property, further add polymerization inhibitor or the antioxidant such as quinones, polyatomic phenol, phenol, phosphorous acid esters and sulphur class.
Further, in the photosensitive adhesive of present embodiment, can also suitably contain filler.As filler, for example, can enumerate inorganic filler and the organic fillers such as charcoal and rubber series filler such as the metallic stuffings such as silver powder, bronze, copper powder and nickel powder, aluminium oxide, aluminium hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicates, magnesium silicate, calcium oxide, magnesium oxide, aluminium oxide, aluminium nitride, crystallinity silicon dioxide, amorphism silicon dioxide, boron nitride, titanium dioxide, glass, iron oxide and pottery, and no matter be what kind and shape etc., can use with being not particularly limited.
Above-mentioned filler can suitably use according to desirable function.For example, for photosensitive adhesive being given conductivity, thermal conductivity and thixotropy etc., can add metallic stuffing.In order to give thermal conductivity, low heat expansion and agent of low hygroscopicity etc. to the photosensitive adhesive layer, can add nonmetal inorganic filler, and for the photosensitive adhesive layer being given toughness etc., can add organic filler.
These metallic stuffings, inorganic filler or organic filler can be used separately a kind or will be used in combination more than 2 kinds.Wherein, consider with the viewpoint of the desired conductivity of adhesives, thermal conductivity or low moisture-absorption characteristics that from giving semiconductor device the filler of preferred insulating properties is considered in preferable alloy filler or inorganic filler from the viewpoint that can give insulating properties.In inorganic filler or insulating properties filler, from the favorable dispersibility for photosensitive adhesive, and the viewpoint consideration that when heating, can give high bonding force, more preferably silica filler.
Above-mentioned filler, preferably its average grain diameter is that the following and maximum particle diameter of 10 μ m is below the 30 μ m, and more preferably its average grain diameter is that the following and maximum particle diameter of 5 μ m is below the 20 μ m.If average grain diameter surpasses 10 μ m and maximum particle diameter surpasses 30 μ m, then have fully to obtain the tendency that fracture toughness improves effect.In addition, the lower limit of average grain diameter and maximum particle diameter is not particularly limited, and all is more than the 0.001 μ m usually.
The amount of above-mentioned filler can be determined according to the characteristic of giving or function, but with respect to the total amount of resinous principle ((A) become grade) and filler, is preferably 0～50 quality %, 1～40 quality % more preferably, and 3～30 quality % more preferably.By increasing the amount of filler, can realize low Alphaization, low moisture absorption, high elastic modulus, and can the Effective Raise cutting (cuttability that carries out with cutting tool), wire-bonded (ultrasonic wave efficient), the adhesive strength when heating.
If amount of filler is increased to more than necessity, the viscosity rise of photosensitive adhesive is then arranged, the perhaps impaired tendency of the hot pressing of photosensitive adhesive, so the consumption of filler preferably drops in the above-mentioned scope.In order to obtain the balance of desirable characteristics, should determine only amount of filler.Mixing when using filler and mixing can suitably be made up the dispersion machine such as common mixer, mixing and kneading machine, three-roller and ball mill and carried out.
For the interface that makes storeroom of the same race not in conjunction with good, in the photosensitive adhesive of present embodiment, can add various coupling agents.As coupling agent, for example, can enumerate silane series coupling agent, titanium is that coupling agent and aluminium are coupling agent etc.Wherein, consider from effective aspect, preferred silane is coupling agent, and more preferably has the compound of thermosetting functional group, methacrylate and/or the acrylate isoradial polymerism functional groups such as epoxy radicals.The boiling point of above-mentioned silane series coupling agent and/or decomposition temperature are preferably more than 150 ℃, more preferably more than 180 ℃, and more preferably more than 200 ℃.That is to say, most preferably using boiling point and/or decomposition temperature is more than 200 ℃, and has the silane series coupling agent of thermosetting functional group, methacrylate and/or the acrylate isoradial polymerism functional groups such as epoxy radicals.The amount of above-mentioned coupling agent is considered from its effect, thermal endurance and cost aspect, with respect to used photosensitive adhesive 100 mass parts, is preferably 0.01～20 mass parts.
For adion impurity and the insulating reliability when making moisture absorption good, in the photosensitive adhesive of present embodiment, can also further add ion capturing agent.As this ion capturing agent, be not particularly limited, for example, can enumerate triazine thiol compound, phenol is that the known conduct such as reducing agent prevents that copper is ionized and compound, pulverous bismuth system, antimony system, magnesium system, aluminium system, zirconium system, calcium system, titanium system, the tin of the anti-copper evil agent of stripping are and their inorganic compounds such as mixed stocker.As concrete example, be not particularly limited, the inorganic ion scavenger that East Asia synthetic (strain) system is arranged, trade name, IXE-300(antimony system), IXE-500(bismuth system), IXE-600(antimony, bismuth mixed stocker), IXE-700(magnesium, aluminium mixed stocker), IXE-800(zirconium system), IXE-1100(calcium system) etc.They can use separately a kind or will be more than 2 kinds mix and use.The amount of above-mentioned ion capturing agent is considered from viewpoints such as additive effect, thermal endurance, costs, with respect to 100 mass parts photosensitive adhesives, is preferably 0.01～10 mass parts.
Viewpoint that can stable supplying when supplying with photosensitive adhesive from the peristome of printing forward direction mesh galley, the viewpoint that photosensitive adhesive breaks away from from the mesh peristome during printing, and the voluntarily mobile bubble of photosensitive adhesive layer, the viewpoint of mesh vestige planarization of making by above-mentioned photosensitive adhesive considered after the printing, and the thixotropic index of photosensitive adhesive is preferably 1.0～3.0.If above-mentioned thixotropic index is more than 1.0, then there is the above-mentioned photosensitive adhesive generation that suppresses by print process is supplied with and is coated with to drop down stream etc., thereby can keeps printing the good tendency of shape.Further, if this thixotropic index is below 3.0, the tendency that can suppress by print process is supplied with and the above-mentioned photosensitive adhesive of coating produces " waning " or shows money or valuables one carries unintentionally etc. is arranged then.The higher limit of the thixotropic index of photosensitive adhesive and lower limit can be 1.0,1.2,1.3 or 3.0.
The viscosity of photosensitive adhesive under 25 ℃, supply with the viewpoint of operability of the photosensitive adhesive of photosensitive adhesive etc. during from operation to galley, the viewpoint that photosensitive adhesive breaks away from from the mesh peristome during printing, and the voluntarily mobile bubble of photosensitive adhesive layer, the viewpoint of mesh vestige planarization of making by above-mentioned photosensitive adhesive considered after the printing, is preferably 1～100Pas.Higher limit and the lower limit of the viscosity of photosensitive adhesive under 25 ℃ can be 1Pas, 8.5Pas, 12.8Pas, 16.0Pas or 100Pas.
Above-mentioned viscosity is to use E type rotation viscometer (Tokyo gauge system), the value when measuring under 3 ° of circular cones, 25 ℃, revolution are the condition of 0.5rpm.Thixotropic index is by using E type rotation viscometer, and the value when measuring under 25 ℃, revolution are the condition of 1rpm defines (thixotropic index=(viscosity during 1rpm)/(viscosity during 10rpm)) with the ratio that at 25 ℃, revolution is the value when measuring under the condition of 10rpm.
Embodiment
Below, by enumerating embodiment, the present invention is carried out more specific description.But the present invention is not limited to following examples.
(adjustment of photosensitive adhesive)
At first, in 4 mouthfuls of detachable flasks in being arranged at oil bath, with thermosetting resin and radioactive ray polymerizable compound, stir while under nitrogen atmosphere, be heated to 60 ℃, make its dissolving.Add respectively hot curing initator and Photoepolymerizationinitiater initiater in the solution of gained, join in the mixing and kneading machine, mixing, the deaeration of then further carrying out 1 hour below 5Torr is mixing.Further, mixing by adding radioactive ray polymerizable compound and deaeration, adjust viscosity, obtain the photosensitive adhesive that each composition is ratio shown in the table 1.Viscosity and the thixotropic index of each photosensitive adhesive under 25 ℃ is as shown in table 1.
(formation of photosensitive adhesive layer)
Use is provided with the MK-838SV printing machine (Minami Co., Ltd. system) of V-screen V160 mesh galley (the NBC Meshtec of Co., Ltd. system), is that the silicon wafer back side printing coating of 50 μ m is the toroidal of 6 inches φ with the photosensitive adhesive of gained being of a size of 8 inches φ, thickness.The result of the situation by the photosensitive adhesive after the Visual Confirmation printing, can arrange does not show money or valuables one carries unintentionally waits and uniform photosensitive adhesive layer.
(mensuration of the surperficial viscous force of the photosensitive adhesive layer behind the B rank)
As embodiment 1～4, use parallel exposing machine (the fine jade Mi Nasi of Co., Ltd. makes, " ML-210FM mask aligner " (trade name)), under nitrogen atmosphere, with 1000mJ/cm 2Amount to exposing by silk screen print method formed photosensitive adhesive layer on silicon wafer, make photosensitive adhesive layer B rank.In addition, as a comparative example 1, prepare to have printed the silicon wafer of the photosensitive adhesive identical with embodiment 1, put in 100 ℃ the drying machine 1 hour, carry out the B rank by heating.Behind the B rank, make the firmly probe viscous force testing machine of Co., Ltd. of generation section manufacturing, at probe diameter: 5.1mm, traction peeling rate: 10mm/s, contact loading: 100gf/cm 2, time of contact: 1s condition under, the surperficial viscous force of the photosensitive adhesive layer under measuring 30 ℃.Surperficial viscous force behind the B rank is as shown in table 1.
(observation of the silicon wafer warpage behind the B rank)
Observe the silicon wafer behind the B rank of gained in above-mentioned " mensuration of the surperficial viscous force of the photosensitive adhesive layer behind the B rank ", the formation of result's gained in embodiment 1～4 silicon wafer of photosensitive adhesive layer do not see warpage.But, in the comparative example 1 formation of gained the silicon wafer of photosensitive adhesive layer, observed the warpage of silicon wafer along with heating, and the difference of height of the end of silicon wafer and central portion is about 1.5cm.The observed result of the silicon wafer warpage behind the B rank is as shown in table 1.
(pick)
Silicon wafer one side lamination dicing tape at the silicon wafer that has formed the photosensitive adhesive layer by silk screen print method, and after being arranged on the wafer ring, use cutter sweep (Disco Corp's system, " DAD-3220 " (trade name)), be cut into the square of 10 * 10mm.In embodiment 1～4, the result of the silicon wafer situation after confirming to cut, silicon can be by shortcoming ground cutting.In addition, pick up 10 silicons from dicing tape, photosensitive adhesive is not transferred on the dicing tape as a result, and pick is also good.On the other hand, in comparative example 1, the viscous force of the photosensitive adhesive layer behind the B rank is excessively strong, can't cut.
(mensuration of shear strength)
Will with the above-mentioned silicon with bond layer that obtains equally (5 * 5mm's is square) hot pressing (200gf, 120 ℃, 3 seconds) on the silicon (8 * 8mm's is square) of preparing in addition, in baking oven, under 180 ℃, carry out 1 hour be heating and curing.Use automatic adhesive force tester (the Arctec(ア ー of Co., Ltd. Network テ ッ Network) system, " DAGE SERIES4000 " (trade name)) shear strength under measuring 250 ℃.Measurement result is as shown in table 1.
[table 1]
Figure BDA00002806172400321
* 1: the quality % take the photosensitive adhesive total amount as benchmark
* 2: the mass parts when the radioactive ray polymerizable compound is 100 mass parts
* 3: the mass parts when thermosetting resin is 100 mass parts
* 4: because the viscous force behind the B rank is crossed by force and can't be measured
* 5: because the viscous force behind the B rank is strong, can't cut, so can not measure
* 6: the difference of height of end and central portion is 1.5cm
Each mark in the table 1 represents following implication.
YDCN700-7: Dongdu changes into (strain), the cresols phenolic resin varnish type epoxy resin
YDF-8170C: Dongdu changes into (strain), bisphenol f type epoxy resin
The EP1032H60:JER(strain), three (hydroxy phenyl) methane type solid epoxy
ARONIX M-140: (strain) synthesized in East Asia, N-acryloxy ethyl hexahydro phthalimide
FA-220M: Hitachi changes into industry (strain), polyethylene glycol #200 dimethylacrylate
I-819: vapour bar Japan (strain), two (2,4,6-the trimethylbenzoyl)-phosphine oxides of phenyl
I-379EG: vapour bar Japan (strain), 2-(dimethylamino)-the 2-(4-methyl-benzyl)-1-(4-morpholino phenyl)-the 1-butanone
1B2PZ: four countries change into industry (strain), 1-benzyl-2-phenylimidazole.
Description of reference numerals
1 is the galley housing, 2 is the part of using the resin landfill in the mesh galley, 3 is the peristome in the mesh galley, 4 is squeegee, 5 is photosensitive adhesive, 6 is semiconductor wafer, 7 is the photosensitive adhesive layer, 8 for carrying out the photosensitive adhesive layer behind the B rank by exposure, 9 is framework, 10 are the cutting film, 11 is the semiconductor chip with bond layer, 12 is cutter, 13a is the 1st layer of semiconductor chip, 13b is the 2nd layer of semiconductor chip, 14 is holding components, 15 is encapsulant, 16 for engaging the photosensitive adhesive layer of the 1st layer of semiconductor chip and holding components, 17 for engaging the photosensitive adhesive layer of the 2nd layer of semiconductor chip and the 1st layer of semiconductor chip, 18 is bonding wire, 20 is the semiconductor wafer with bond layer.

Claims (9)

1. manufacture method with the semiconductor wafer of bond layer, it comprises by the whole surface-coated photosensitive adhesive of silk screen print method in the one side of semiconductor wafer, forms the operation of photosensitive adhesive layer; With the operation that makes described photosensitive adhesive layer B rank by exposure.
2. manufacture method as claimed in claim 1, wherein said photosensitive adhesive contains thermosetting resin, radioactive ray polymerizable compound and Photoepolymerizationinitiater initiater.
3. manufacture method as claimed in claim 1 or 2, wherein said photosensitive adhesive further contains the hot curing initator.
4. such as each the described manufacture method in the claim 1～3, the viscosity of wherein said photosensitive adhesive under 25 ℃ is 1～100Pas, and the thixotropic index of described photosensitive adhesive is 1.0～3.0.
5. be used for the photosensitive adhesive of manufacture method claimed in claim 1, it contains thermosetting resin, radioactive ray polymerizable compound and Photoepolymerizationinitiater initiater.
6. photosensitive adhesive as claimed in claim 5, it further contains the hot curing initator.
7. such as claim 5 or 6 described photosensitive adhesives, its viscosity under 25 ℃ is 1～100Pas, and thixotropic index is 1.0～3.0.
8. semiconductor device by following method gained, described method comprises the semiconductor wafer singualtion with bond layer by each the described manufacture method gained in the claim 1～4, obtains the operation with the semiconductor chip of bond layer; Be adhered to the operation of holding components or other semiconductor chip with the semiconductor chip with described semiconductor chip with bond layer.
9. silk screen printing photosensitive adhesive, it contains thermosetting resin, radioactive ray polymerizable compound and Photoepolymerizationinitiater initiater, and the viscosity under 25 ℃ is 1～100Pas, and thixotropic index is 1.0～3.0.
CN2011800379173A 2010-08-03 2011-07-29 Method for manufacturing semiconductor wafer provided with adhesive layer, photosensitive adhesive, and semiconductor device Pending CN103053016A (en)

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