JP6817813B2 - Work fixing sheet with resin layer - Google Patents

Description

The present invention relates to a work fixing sheet with a resin layer, which comprises a pressure-sensitive adhesive layer on a base film and a curable resin layer on the pressure-sensitive adhesive layer.
This application claims priority based on Japanese Patent Application No. 2014-192505 filed in Japan on September 22, 2014, the contents of which are incorporated herein by reference.

A work fixing sheet with a resin layer having an adhesive layer on a base film and a curable resin layer on the adhesive layer is, for example, a step of dicing a semiconductor wafer and then picking up a semiconductor chip. It is suitable for use in a process up to die bonding in which the picked up semiconductor chip is bonded to a substrate, a lead frame, another semiconductor chip, or the like. For example, at the time of manufacturing a semiconductor device, the curable resin layer of the work fixing sheet with a resin layer functions as an adhesive film for dicing, and the work fixing sheet with a resin layer is attached to a semiconductor wafer by the curable resin. The work fixing sheet with a resin layer is used as a dicing die bonding sheet when dicing is performed in this state.

In addition to the above applications, the work fixing sheet with a resin layer also serves as a protective film for a semiconductor wafer or a semiconductor chip (flip chip) and a dicing sheet, or when the flip chip is adhered to a chip mounting portion. It can also be used as both an adhesive film and a back grind sheet.
In any of the applications, the work fixing sheet with the resin layer is in a state of being attached to the semiconductor chip by the curable resin layer, and the adhesive layer is further peeled off from the curable resin layer together with the base film. At this time, if necessary, the adhesiveness of the pressure-sensitive adhesive layer may be lowered by carrying out a polymerization reaction in the pressure-sensitive adhesive layer.

On the other hand, the strength of the curable resin layer of the work fixing sheet with the resin layer is improved by containing the filler. On the other hand, it may be difficult for the filler to be uniformly dispersed in the curable resin layer. In addition, the filler may fall off from the cured film after the curable resin layer containing the filler is cured. Therefore, a work fixing sheet with a resin layer provided with a curable resin layer that does not substantially contain a filler is desired. By the way, unlike a work fixing sheet with a resin layer, an adhesive sheet in which an adhesive layer is directly attached to a semiconductor wafer without using a curable resin layer is known. As such a pressure-sensitive adhesive sheet, for example, a pressure-sensitive adhesive layer using a base polymer having a structural unit derived from a methacrylate monomer having an alkyl group having 10 to 17 carbon atoms and two other specific types of monomers. (See Patent Document 1).

Japanese Unexamined Patent Publication No. 2012-136678

However, Patent Document 1 does not describe or suggest that a curable resin layer is provided on the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet and the constituent components of the curable resin layer. When a work fixing sheet with a resin layer having a curable resin layer that does not substantially contain a filler is used, the semiconductor chip can be easily picked up without applying a large external force, that is, so-called easy pick-up property. There was a problem that the amount was reduced.

The present invention has been made in view of the above circumstances, and comprises providing a pressure-sensitive adhesive layer on a base film and providing a curable resin layer substantially free of a filler on the pressure-sensitive adhesive layer, and a semiconductor. An object of the present invention is to provide a work fixing sheet with a resin layer, which has an easy pick-up property for a chip.

In order to solve the above problems, the present invention is a work fixing sheet with a resin layer having a pressure-sensitive adhesive layer on a base film and a curable resin layer on the pressure-sensitive adhesive layer. Contains a (meth) acrylic acid alkyl ester polymer obtained by polymerizing a monomer containing a (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms in an alkyl group, and is the (meth) acrylic acid alkyl ester polymer. The ratio of the (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms in the alkyl group to the total mass of all the monomers used in the polymerization is 70% by mass or more. The curable resin layer contains a polymer component (a) and a curable component (b), and the total content of the polymer component (a) and the curable component (b) of the curable resin layer is It is 95% by mass or more with respect to the total amount of the curable resin layer, and the polymer component (a) is an acrylic resin, a polyester resin (excluding unsaturated polyester resin), an acrylic urethane resin, and a rubber polymer. , Or a phenoxy resin, with a resin layer, wherein the curable component (b) is an epoxy-based thermosetting resin, a thermosetting polyimide resin, a urethane resin, an unsaturated polyester resin, or a silicone resin. Provide a work fixing sheet.
In the work fixing sheet with a resin layer of the present invention, the curable resin layer further contains a coupling agent (e), and the content of the coupling agent (e) in the curable resin layer is the polymer. The total content of the component (a) and the curable component (b) is preferably 0.1 to 5 parts by mass with respect to 100 parts by mass.
In the work fixing sheet with a resin layer of the present invention, the curable resin layer contains an acrylic resin as the polymer component (a), and the acrylic resin is contained in the total amount of the solid content of the curable resin layer. The amount is preferably 50% by mass or more.
In the work fixing sheet with a resin layer of the present invention, the content of the curable component (b) in the curable resin layer is 1 to 100 mass by mass with respect to 100 parts by mass of the content of the polymer component (a). The part is preferable.

According to the present invention, the effect of providing a pressure-sensitive adhesive layer on the base film and substantially containing no filler, that is, a curable resin layer containing no filler or using a filler is effective. Provided is a work fixing sheet with a resin layer, which comprises a curable resin layer containing a filler to a negligible degree on the pressure-sensitive adhesive layer and has easy pick-up property for a semiconductor chip.

It is sectional drawing which shows typically the work fixing sheet with a resin layer which concerns on this invention.

<Work fixing sheet with resin layer>
The work fixing sheet with a resin layer according to the present invention is a work fixing sheet with a resin layer having a pressure-sensitive adhesive layer on a base film and a curable resin layer on the pressure-sensitive adhesive layer. The layer contains a (meth) acrylic acid alkyl ester polymer obtained by polymerizing a monomer containing a (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms in an alkyl group, and the curable resin layer is a polymer. It contains the component (a) and the curable component (b), and the total content of the polymer component (a) and the curable component (b) of the curable resin layer is based on the total amount of the curable resin layer. It is characterized in that it is 95% by mass or more.
In the present specification, the laminated structure of the base film and the pressure-sensitive adhesive layer is referred to as a work fixing sheet.
As used herein, the term "polymerization" includes both homopolymerization of a single type of monomer (also referred to as a monomer) and copolymerization of a plurality of types of monomers. Therefore, as used herein, the term "polymer" includes both a homopolymer obtained by homopolymerizing a single type of monomer and a copolymer obtained by copolymerizing a plurality of types of monomers.

The work fixing sheet with a resin layer is a die for, for example, dicing a semiconductor wafer and then picking up a semiconductor chip to bond the picked up semiconductor chip to a substrate, a lead frame, another semiconductor chip, or the like. It is suitable for use in the process up to bonding. In this case, the curable resin layer (resin layer) functions as an adhesive film for die bonding, and the work fixing sheet with the resin layer is attached to the semiconductor wafer by the curable resin layer for dicing. In addition, the work fixing sheet with a resin layer is used as a dicing die bonding sheet.

The work fixing sheet with a resin layer has sufficient easy pick-up property so that a work (semiconductor chip) can be easily picked up even with a small external force. Therefore, damage such as cracking when picking up a semiconductor chip having a thin thickness is suppressed. When the pressure-sensitive adhesive layer contains a compound capable of a polymerization reaction, such easy pick-up property is further improved by reducing the tackiness of the pressure-sensitive adhesive layer after the polymerization reaction.
In a work fixing sheet with a resin layer, the above-mentioned easy pick-up property is usually lowered when the curable resin layer does not substantially contain a filler. On the other hand, in the work fixing sheet with a resin layer according to the present invention, the pressure-sensitive adhesive layer is obtained by polymerizing a monomer containing a (meth) acrylic acid alkyl ester having an alkyl group having 10 to 18 carbon atoms (meth). By containing the acrylic acid alkyl ester polymer, the curable resin layer has good pick-up property even if it does not substantially contain a filler. When the alkyl group of the (meth) acrylic acid alkyl ester used for the pressure-sensitive adhesive layer has 9 or less carbon atoms, the work fixing sheet with the resin layer can be used when the curable resin layer does not substantially contain a filler. , Does not have the ease of picking up semiconductor chips. On the other hand, the alkyl group of the (meth) acrylic acid alkyl ester used for the pressure-sensitive adhesive layer having 19 or more carbon atoms is difficult to handle due to its low solubility.

Normally, when a semiconductor chip is directly fixed to the pressure-sensitive adhesive layer using a work fixing sheet having a pressure-sensitive adhesive layer on a base film, the semiconductor chip is peeled off from the pressure-sensitive adhesive layer after dicing (pickup). To do). When the pressure-sensitive adhesive layer contains a component that polymerizes by irradiation with energy rays, the pressure-sensitive adhesive layer can be irradiated with energy rays to reduce the adhesiveness of the pressure-sensitive adhesive layer, and then pickup can be performed.
On the other hand, when a semiconductor chip is fixed to the curable resin layer using a work fixing sheet with a resin layer, the semiconductor chip is peeled from the adhesive layer while being integrated with the curable resin layer after dicing. It is peeled off (picked up) from the adhesive layer after being radiated or, in some cases, irradiated with energy rays.
Then, usually, the work fixing sheet with a resin layer is not easy to peel off and tends to be inferior in peelability (easy pick-up property) as compared with the work fixing sheet not provided with a curable resin layer.
On the other hand, the work fixing sheet with a resin layer according to the present invention is excellent in peelability (easy pick-up property) by adopting the above configuration.

Further, the work fixing sheet with a resin layer according to the present invention is also suitable for use as a protective film forming sheet that protects the back surface of the flip chip. In this case, the curable resin layer (resin layer) functions as a film for forming a protective film for flip chips, and when dicing is performed in a state where a work fixing sheet with a resin layer is attached to a semiconductor wafer by the curable resin layer. In addition, it is used as a protective sheet for a semiconductor wafer or a semiconductor chip (flip chip) and a dicing sheet.

Further, in the work fixing sheet with a resin layer according to the present invention, the curable resin layer is attached to the electrode forming surface of the semiconductor wafer for flip chips, the surface opposite to the electrode forming surface of the semiconductor wafer is ground, and then the electrodes It can also be used when the work fixing sheet is peeled off while leaving a curable resin layer on the formed surface. In this case, the curable resin layer (resin layer) then functions as an adhesive film when the flip chip is adhered to the chip mounting portion, and the work fixing sheet with the resin layer serves as both the adhesive film and the back grind sheet. Use.

FIG. 1 is a cross-sectional view schematically showing a work fixing sheet with a resin layer according to the present invention.
The work fixing sheet 10 with a resin layer shown in FIG. 1 is provided with an adhesive layer 12 on a base film 11 and a curable resin layer 13 on the pressure-sensitive adhesive layer 12, and is a work fixing sheet 1. It has a structure in which a curable resin layer 13 is provided on the pressure-sensitive adhesive layer 12. Further, the work fixing sheet 10 with a resin layer further includes a release film 14 on the curable resin layer 13.
In the work fixing sheet 10, the pressure-sensitive adhesive layer 12 is laminated on the surface 11a of the base film 11, and the curable resin layer 13 is laminated on a part of the surface 12a of the pressure-sensitive adhesive layer 12. Then, of the surface 12a of the pressure-sensitive adhesive layer 12, the release film 14 is laminated on the exposed surface on which the curable resin layer 13 is not laminated and on the surface 13a (upper surface and side surface) of the curable resin layer 13. There is.
However, the work fixing sheet with a resin layer according to the present invention is not limited to the one shown in FIG.

[Base film]
The material of the base film is preferably various resins, and specifically, polyethylene (low density polyethylene (LDPE), linear low density polyethylene (LLDPE), high density polyethylene (HDPE, etc.)), polypropylene, polymer. , Polybutadiene, polymethylpentene, polyvinyl chloride fill, vinyl chloride polymer, polyethylene terephthalate, polybutylene terephthalate, polyurethane, polyurethane acrylate, polyimide, vinyl ethylene acetate polymer, ionomer resin, ethylene / (meth) acrylic acid polymer, Examples thereof include ethylene / (meth) acrylic acid ester polymers, polystyrene, polycarbonate, fluororesins, water additives, modified products, crosslinked products, and polymers of any of these resins.
In addition, in this specification, "(meth) acrylic" is a concept including both "acrylic" and "methacryl".

The base film may be composed of one layer (single layer), may be composed of two or more layers, or may be composed of a plurality of layers, and the materials of the respective layers may be the same or different. Well, only part of it may be the same.

The thickness of the base film can be appropriately selected depending on the intended purpose, but is preferably 50 to 300 μm, more preferably 60 to 100 μm.
The above-mentioned "thickness of the base film" is a value represented by the average of the thickness measured by a contact type thickness gauge at any five points.

In order to improve the adhesiveness of the base film to the adhesive layer provided on it, the base film is subjected to unevenness treatment by sandblasting treatment, solvent treatment, corona discharge treatment, electron beam irradiation treatment, plasma treatment, ozone / ultraviolet rays, etc. The surface may be subjected to oxidation treatment such as irradiation treatment, flame treatment, chromic acid treatment, and hot air treatment. Further, the base film may be one whose surface has been subjected to a primer treatment.
Among these, the base film is particularly preferably one whose surface has been subjected to electron beam irradiation treatment from the viewpoint of suppressing the generation of fragments of the base film due to the friction of the blade during dicing.

[Adhesive layer]
The pressure-sensitive adhesive layer contains the (meth) acrylic acid alkyl ester polymer.
The pressure-sensitive adhesive layer can be formed by using a pressure-sensitive adhesive composition containing a target component such as the (meth) acrylic acid alkyl ester polymer. The ratio of the contents of the non-volatile components in the pressure-sensitive adhesive composition is the same in the pressure-sensitive adhesive layer.

The thickness of the pressure-sensitive adhesive layer can be appropriately selected depending on the intended purpose, but is preferably 1 to 100 μm, more preferably 1 to 60 μm, and particularly preferably 1 to 30 μm.
The above-mentioned "thickness of the adhesive layer" is a value represented by the average of the thickness measured by a contact-type thickness gauge at any five points. If it is difficult to apply the contact-type thickness gauge directly to the pressure-sensitive adhesive layer, the entire film may be laminated in the same manner as above with other films such as a base film and a release material described later. It may be calculated by measuring the thickness and taking the difference from the thickness of the other overlaid films (measured by the same method as described above).

((Meta) acrylic acid alkyl ester polymer)
The (meth) acrylic acid alkyl ester polymer is a polymer obtained by polymerizing a monomer containing a (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms in the alkyl group constituting the alkyl ester. In addition, in this specification, the description of a simple "(meth) acrylic acid alkyl ester" refers to the above "(meth) acrylic acid alkyl ester having 10 to 18 carbon atoms of an alkyl group" unless otherwise specified. It shall mean.
The alkyl group having 10 to 18 carbon atoms in the (meth) acrylic acid alkyl ester may be linear, branched chain or cyclic, and when cyclic, it may be monocyclic or polycyclic. , It is preferably linear or branched.

Preferred (meth) acrylic acid alkyl esters having 10 to 18 carbon atoms in the alkyl group are decyl (meth) acrylate, undecyl (meth) acrylate, and dodecyl (meth) acrylate (lauryl (meth) acrylate). ), (Meta) tridecyl acrylate, (meth) tetradecyl acrylate ((meth) myristyl acrylate), (meth) pentadecyl acrylate, (meth) hexadecyl acrylate ((meth) palmityl acrylate), (meth) Alkyl (meth) acrylate having a chain of alkyl groups such as heptadecyl acrylate, octadecyl (meth) acrylate (stearyl (meth) acrylate), isooctadecyl (meth) acrylate (isostearyl (meth) acrylate) Esters; examples include (meth) acrylic acid cycloalkyl esters such as (meth) acrylic acid isobornyl and (meth) acrylic acid dicyclopentanyl. Further, as the (meth) acrylic acid alkyl ester having an alkyl group having 10 to 18 carbon atoms, among the above, dodecyl (meth) acrylic acid (lauryl (meth) acrylic acid) or isooctadecyl (meth) acrylic acid (Isostearyl (meth) acrylate) is particularly preferable from the viewpoint of obtaining the effect of improving the ease of picking up the work.

As the (meth) acrylic acid alkyl ester polymer, an energy ray-polymerizable polymer that is polymerized by irradiation with energy rays can also be used, and such a polymer preferably has a hydroxyl group and is further urethane. Examples thereof include those having a polymerizable group in the side chain via a bond. Such a (meth) acrylic acid alkyl ester polymer is crosslinked by, for example, the hydroxyl group contained therein reacting with an isocyanate group in an isocyanate-based crosslinking agent described later. Further, such an acrylic acid ester polymer has a polymerizable group in the side chain, so that, for example, a polymer reaction is carried out by separately irradiating an energy ray with a low molecular weight energy ray-polymerizable compound. However, by reducing the adhesiveness of the pressure-sensitive adhesive layer after the polymerization reaction, the peelability from the adherend is improved, and the effect of improving the ease of picking up the work can be obtained. Further, since it is not necessary to separately use a low molecular weight energy ray-polymerizable compound, as will be described later, when a curable resin layer is formed on the pressure-sensitive adhesive layer, such a low molecular weight energy ray-polymerizable compound is formed. The transition from the pressure-sensitive adhesive layer to the curable resin layer is suppressed, and changes in the characteristics of the curable resin layer are suppressed.

The preferred (meth) acrylic acid alkyl ester polymer described above is usually obtained by polymerizing a composition comprising the (meth) acrylic acid alkyl ester and a hydroxyl group-containing monomer to obtain a polymer. It is obtained by reacting the hydroxyl group of the polymer with the isocyanate group of an isocyanate group and a compound having a polymerizable group. Here, in order to react the hydroxyl group and the isocyanate group (form a urethane bond), it is necessary to further use a catalyst such as an organic tin compound. This catalyst remains in the reaction system after the reaction is completed, but it is difficult to completely remove it from the obtained (meth) acrylic acid alkyl ester polymer, or even if it can be removed, a step for that purpose is required. The addition complicates the operation and reduces the productivity. Therefore, usually, a method of not removing the catalyst from the reaction system after the reaction is completed is adopted, so that the catalyst remains in the obtained (meth) acrylic acid alkyl ester polymer.

The catalyst remaining in the (meth) acrylic acid alkyl ester polymer can allow an unintended cross-linking reaction to proceed when the pressure-sensitive adhesive composition using such a polymer is stored. This tendency is particularly strong when the number of moles of the isocyanate group in the isocyanate-based cross-linking agent is large with respect to 1 mole of the hydroxyl group in the (meth) acrylic acid alkyl ester polymer.
On the other hand, in the present invention, even when the number of moles of the above-mentioned isocyanate group is large, the progress of the unintended cross-linking reaction as described above is suppressed by using the reaction retarder described later. Will be done. The residual amount (content) of the catalyst in the (meth) acrylic acid alkyl ester polymer is preferably 2% by mass or less, preferably 1% by mass or less, from the viewpoint of further improving the suppressing effect. More preferably, it is more preferably 0.5% by mass or less.

Among the (meth) acrylic acid alkyl ester polymers, more preferable polymers include the (meth) acrylic acid alkyl ester and the hydroxyl group-containing (meth) acrylic acid ester as essential monomers. It is a reaction product of the copolymer of the above and a compound having an isocyanate group and a polymerizable group, and the hydroxyl group of the copolymer and the isocyanate group of the compound having the isocyanate group and the polymerizable group are combined. The above-mentioned reactant can be exemplified.

Examples of the hydroxyl group-containing (meth) acrylic acid ester include hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate.

Examples of the compound having an isocyanate group and a polymerizable group include isocyanate group-containing (meth) acrylic acid alkyl esters such as 2-methacryloyloxyethyl isocyanate.

The preferred (meth) acrylic acid alkyl ester polymer described above may be a reaction of any compound in addition to the essential monomers and compounds described above, and the monomer is polymerized as the optional compound. It may be an ester.
Examples of the optional monomer include hydroxyl group-free (meth) acrylic acid ester, (meth) acrylic acid, itaconic acid, and non- (meth) acrylic acid-based monomer, which do not correspond to the (meth) acrylic acid alkyl ester. Can be exemplified.

Examples of the hydroxyl group-free (meth) acrylate ester include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, and (meth). ) Hexyl acrylate, (meth) heptyl acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-nonyl (meth) acrylate, (meth) acrylic (Meta) acrylic acid alkyl ester in which the alkyl group constituting the alkyl ester such as isononyl acid is linear or branched and has 1 to 9 carbon atoms; aralkyl (meth) acrylate such as benzyl (meth) acrylate; Cycloalkenyl (meth) acrylates such as dicyclopentenyl (meth) acrylate; cycloalkenyloxyalkyl (meth) acrylates such as dicyclopentenyloxyethyl (meth) acrylate; imide (meth) acrylate; glycidyl such as glycidyl (meth) acrylate Group-containing (meth) acrylate and the like can be exemplified.

Examples of the non- (meth) acrylic monomer include vinyl acetate, acrylonitrile, styrene, and N-methylolacrylamide.

Used for preparing the (meth) acrylic acid alkyl ester polymer such as the (meth) acrylic acid alkyl ester, a hydroxyl group-containing (meth) acrylic acid ester, a compound having an isocyanate group and a polymerizable group, and any of the above compounds. The components (components of the polymer) may be only one type or two or more types.

The (meth) acrylic acid alkyl ester polymer (as described above, in a preferred form of the (meth) acrylic acid alkyl ester polymer having a hydroxyl group and further having a polymerizable group in the side chain via a urethane bond (Not limited to), the proportion of the (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms in the above-mentioned alkyl group is 60% by mass or more with respect to the total mass of all the monomers used for the polymerization. Those having an amount of 70% by mass or more are more preferable, and those having an amount of 75% by mass or more are particularly preferable. The proportion of the (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms in the alkyl group in the above (meth) acrylic acid alkyl ester polymer is the total mass of all the monomers used in the polymerization. On the other hand, it is 100% by mass or less.

The (meth) acrylic acid alkyl ester polymer contained in the pressure-sensitive adhesive layer may be of only one type or of two or more types.
Further, in the monomer containing the (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms of the alkyl group, the monomer contained in the monomer is not particularly limited, but for example, the above-mentioned (meth) acrylic acid alkyl Examples thereof include hydroxyl group-containing (meth) acrylic acid ester, hydroxyl group-free (meth) acrylic acid ester, (meth) acrylic acid, itaconic acid, and non- (meth) acrylic monomer, which do not correspond to esters. Specific examples of the meta) acrylic acid ester, the hydroxyl group-free (meth) acrylic acid ester, and the non- (meth) acrylic acid monomer are the same as those described above.

The content of the (meth) acrylic acid alkyl ester polymer in the pressure-sensitive adhesive layer is preferably 75% by mass or more, and more preferably 80% by mass or more. Then, in order to form such a pressure-sensitive adhesive layer, the content of the (meth) acrylic acid alkyl ester polymer in the pressure-sensitive adhesive composition is relative to the total amount of all components other than the solvent in the pressure-sensitive adhesive composition. It is preferably 75% by mass or more, and more preferably 80% by mass or more. Further, the content of the (meth) acrylic acid alkyl ester polymer in the pressure-sensitive adhesive composition may be 100% by mass.

Preferred examples of the pressure-sensitive adhesive composition include those containing an isocyanate-based cross-linking agent and a reaction retarder in addition to the (meth) acrylic acid alkyl ester polymer. Since such an adhesive composition suppresses the progress of an unintended cross-linking reaction during storage, changes in properties such as viscosity during storage are suppressed, and the storage stability is high.

(Isocyanate cross-linking agent)
The isocyanate-based cross-linking agent is not particularly limited as long as it is a cross-linking agent having an isocyanate group (-N = C = O), and preferably 2,4-tolylene diisocyanate; 2,6-tolylene diisocyanate; 1,3-Xylylene diisocyanate; 1,4-xylene diisocyanate; diphenylmethane-4,4'-diisocyanate;diphenylmethane-2,4'-diisocyanate; 3-methyldiphenylmethane diisocyanate; hexamethylene diisocyanate; isophorone diisocyanate; dicyclohexylmethane-4 , 4'-diisocyanate;dicyclohexylmethane-2,4'-diisocyanate; a compound obtained by adding either or both of tolylene diisocyanate and hexamethylene diisocyanate to all or some hydroxylates of a polyol such as trimethylolpropane; Examples thereof include diisocyanate.

The isocyanate-based cross-linking agent contained in the pressure-sensitive adhesive composition may be only one type or two or more types.

The number of moles of isocyanate groups contained in the isocyanate-based cross-linking agent in the pressure-sensitive adhesive composition is 0.2 times the number of moles of hydroxyl groups of the (meth) acrylic acid alkyl ester polymer in the pressure-sensitive adhesive composition. The above is preferable. With this configuration, the pressure-sensitive adhesive layer has less adhesiveness to the work (curable resin layer, etc.) after being cured by UV irradiation or the like, thereby improving the ease of picking up the work fixing sheet.
On the other hand, in the present invention, the number of moles of isocyanate groups contained in the isocyanate-based cross-linking agent in the pressure-sensitive adhesive composition is the number of moles of hydroxyl groups contained in the (meth) acrylic acid alkyl ester polymer in the pressure-sensitive adhesive composition. It is preferably 3 times or less of the amount. With such a configuration, the effect of suppressing the generation of by-products between the isocyanate-based cross-linking agents becomes higher.
That is, the number of moles of isocyanate groups contained in the isocyanate-based cross-linking agent in the above-mentioned pressure-sensitive adhesive composition is 0. The range is preferably 2 to 3 times.

The content of the isocyanate-based cross-linking agent in the pressure-sensitive adhesive composition may be appropriately adjusted so that the number of moles of the isocyanate groups is within the above-mentioned range, but after satisfying such conditions, the above-mentioned (meth). ) The content of the acrylic acid alkyl ester polymer is preferably 3 to 20 parts by mass, more preferably 5 to 15 parts by mass with respect to 100 parts by mass.

(Reaction delay agent)
The reaction delaying agent suppresses the progress of an unintended cross-linking reaction in the pressure-sensitive adhesive composition during storage.
The (meth) acrylic acid alkyl ester polymer usually contains the catalyst used in its preparation, as described above. Examples of the reaction retarder include those that inhibit the action of this catalyst in the pressure-sensitive adhesive composition, and preferred examples include those that form a chelate complex by chelating the catalyst. For example, when the catalyst is an organic tin compound, a reaction retardant that forms a chelate complex with tin can be exemplified.
More specifically, as a preferable reaction retarder, those having two or more carbonyl groups (-C (= O)-) in the molecule can be exemplified, and those having two carbonyl groups in the molecule can be exemplified. Examples thereof include dicarboxylic acids, keto acids, and diketones.

Among them, as the more preferable reaction retarder, those having a carbonylmethylcarbonyl group (-C (= O) -CH _2- C (= O)-) can be exemplified, and more specifically, malonic acid, Β-keto acids such as acetoacetic acid;
Methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, isopropyl acetoacetate, n-butyl acetoacetate, isobutyl acetoacetate, tert-butyl acetoacetate, methyl propionyl acetate, ethyl propionyl acetate, n-propyl propionyl acetate, propionyl acetate Isopropyl, propionyl acetate n-butyl, propionyl acetate tert-butyl, butyryl acetate methyl, butyryl acetate ethyl, butyryl acetate n-propyl, butyryl acetate isopropyl, butyryl acetate n-butyl, butyryl acetate tert-butyl, isobutyryl acetate methyl, isobutyryl acetate Ethyl, n-propyl isobutyryl acetate, isopropyl isobutyryl acetate, n-butyl isobutyryl acetate, tert-butyl isobutyryl acetate, methyl 3-oxoheptate, ethyl 3-oxoheptate, n-propyl 3-oxoheptate, 3-oxo Isopropyl heptanate, n-butyl 3-oxoheptate, tert-butyl 3-oxoheptate, methyl 5-methyl-3-oxohexanate, ethyl 5-methyl-3-oxohexanate, 5-methyl-3-3 N-propyl oxohexaneate, isopropyl 5-methyl-3-oxohexanoate, n-butyl 5-methyl-3-oxohexanoate, tert-butyl 5-methyl-3-oxohexanoate, 4,4-dimethyl- Methyl 3-oxopentate, ethyl 4,4-dimethyl-3-oxopentate, n-propyl 4,4-dimethyl-3-oxopentate, isopropyl 4,4-dimethyl-3-oxopentate, 4, N-Butyl 4-dimethyl-3-oxopentanoate, tert-butyl 4,4-dimethyl-3-oxopentanoate, methyl benzoyl acetate, dimethyl malonate, diethyl malonate, methyl ethyl malonate, di-n-malonate Β-ketoate esters such as propyl, diisopropyl malonate, di-butyl malonate, ditert-butyl malonate, methyl tert-butyl malonate;
Examples thereof include β-diketone (1,3-diketone) such as acetylacetone and dibenzoylmethane.

The reaction retarder contained in the pressure-sensitive adhesive composition may be only one kind or two or more kinds.

The pressure-sensitive adhesive composition preferably contains 0.01 to 2% by mass of the reaction retarder with respect to the total amount of all the components. When the content of the reaction delaying agent is at least the lower limit value, the pressure-sensitive adhesive composition has a higher effect of suppressing the progress of an unintended cross-linking reaction during storage. Further, when the content of the reaction retarder is not more than the upper limit value, the reaction retarder is volatilized by drying when the pressure-sensitive adhesive layer is provided by applying and drying the pressure-sensitive adhesive composition, and the pressure-sensitive adhesive layer is formed. It is possible to prevent the reaction retarder from remaining excessively inside.

The content of the reaction retarder in the pressure-sensitive adhesive composition may be appropriately adjusted so that the mass ratio in the total amount of all the components of the pressure-sensitive adhesive composition is within the above-mentioned range. After satisfying the conditions, the content of the (meth) acrylic acid alkyl ester polymer is preferably 0.01 to 10 parts by mass and 0.05 to 5 parts by mass with respect to 100 parts by mass. Is more preferable.

(Photopolymerization initiator)
It is more preferable that the pressure-sensitive adhesive composition further contains a photopolymerization initiator in addition to the (meth) acrylic acid alkyl ester polymer, an isocyanate-based cross-linking agent and a reaction retarder.
The photopolymerization initiator may be a known one, and specifically, 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-propyl) ketone, α-hydroxy-α, α'-dimethylacetophenone, etc. Α-Ketol compounds such as 2-methyl-2-hydroxypropiophenone and 1-hydroxycyclohexylphenylketone; methoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 2-methyl -1- [4- (Methylthio) -phenyl] -2-acetophenone compounds such as morpholinopropane-1; benzophenone compounds such as benzoin ethyl ether, benzoin isopropyl ether and anisoin methyl ether; ketals such as benzyl dimethyl ketal Compounds; Aromatic sulfonyl chloride compounds such as 2-naphthalene sulfonyl chloride; Photoactive oxime compounds such as 1-phenone-1,1-propandion-2- (o-ethoxycarbonyl) oxime; Benzophenone, benzoylbenzoic acid , 3,3'-Dimethyl-4-methoxybenzophenone and other benzophenone compounds; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4 Examples thereof include thioxanson compounds such as −dichlorothioxanthone, 2,4-diethylthioxanthone, and 2,4-diisopropylthioxanson; benzophenone; ketone halide; acylphosphinoxide; acylphosphonate and the like.

The content of the photopolymerization initiator in the pressure-sensitive adhesive composition is preferably 0.05 to 20 parts by mass with respect to 100 parts by mass of the content of the (meth) acrylic acid alkyl ester polymer.

(solvent)
It is more preferable that the pressure-sensitive adhesive composition further contains a solvent in addition to the (meth) acrylic acid alkyl ester polymer.
The solvent is not particularly limited, but preferred ones are hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, 2-propanol, isobutyl alcohol (2-methylpropan-1-ol) and 1-butanol; Examples thereof include esters such as ethyl acetate; ketones such as acetone and methyl ethyl ketone; ethers such as tetrahydrofuran; amides such as dimethylformamide and N-methylpyrrolidone (compounds having an amide bond).
The solvent contained in the pressure-sensitive adhesive composition may be only one type or two or more types.

When the pressure-sensitive adhesive composition contains a solvent, the content of the solvent is preferably 40 to 90% by mass, more preferably 50 to 80% by mass, based on the total mass of the pressure-sensitive adhesive composition. ..

(Other ingredients)
The pressure-sensitive adhesive composition does not correspond to the isocyanate-based cross-linking agent, reaction retarder, photopolymerization initiator and solvent as long as the effect of the present invention is not impaired, other than the (meth) acrylic acid alkyl ester polymer. It may contain other components.
The other components may be known, and may be arbitrarily selected depending on the intended purpose, and are not particularly limited, but preferable ones are dyes, pigments, deterioration inhibitors, antistatic agents, flame retardants, silicone compounds, and the like. Examples thereof include various additives such as chain transfer agents.

The pressure-sensitive adhesive composition is obtained by blending the (meth) acrylic acid alkyl ester polymer with components other than the polymer.
The order of addition of each of the above components at the time of blending is not particularly limited, and two or more components may be added at the same time.
The method of mixing each component at the time of blending is not particularly limited, and for example, a method of rotating and mixing a stirrer or a stirring blade; a method of mixing using a mixer; a method of adding ultrasonic waves and the like are known. The method may be appropriately selected from the above methods.
The temperature and time at the time of adding and mixing each component are not particularly limited as long as each compounding component does not deteriorate, and may be appropriately adjusted, but the temperature is preferably 15 to 30 ° C.

[Curable resin layer]
The curable resin layer contains a polymer component (a) and a curable component (b), and the total content of the polymer component (a) and the curable component (b) of the curable resin layer is It is 95% by mass or more, preferably 97% by mass or more, more preferably 98% by mass or more, and may be 100% by mass with respect to the total amount of the curable resin layer. Such a curable resin layer does not substantially contain a filler (filler (c) described later). Further, in the present invention, even if such a curable resin layer is provided, the work fixing sheet with the resin layer has easy pick-up property as described above. Further, since the curable resin layer does not substantially contain the filler, the work fixing sheet with the resin layer according to the present invention has a curable resin as the filler, which is peculiar to the case where the filler is contained. It is in a non-uniformly dispersed state in the layers, and does not have a problem that the filler falls off from the cured film after the curable resin layer is cured.
In addition, in this specification, "the curable resin layer does not substantially contain a filler" means that the curable resin layer does not contain a filler at all, or the effect of using a filler is ignored. It means that the curable resin layer contains only a small amount of filler to the extent that it can be obtained. Specifically, the filler contained in the curable resin layer is less than 5% by mass, preferably less than 3% by mass, based on the total solid content of the curable resin composition forming the curable resin layer. It means that it is preferably less than 1% by mass.

The curable resin layer can be formed by using a curable resin composition containing a target component such as the polymer component (a) and the curable component (b). The ratio of the contents of the non-volatile components in the curable resin composition is the same in the curable resin layer.

In the present invention, the polymer component (a) is a component that can be regarded as being formed by a polymerization reaction of a polymerizable compound. Further, the curable component (b) is a component capable of a curing (polymerization) reaction. In the present invention, the polymerization reaction also includes a polycondensation reaction.
The polymer component (a) and the curable component (b) are the main constituent components of the curable resin layer, which are necessary for the curable resin layer to exert its effect .

The thickness of the curable resin layer can be appropriately selected depending on the intended purpose, but is preferably 1 to 100 μm, more preferably 5 to 75 μm, and particularly preferably 5 to 50 μm. Further, the average thickness of the curable resin layer can be obtained by the same measuring method as the average thickness of the pressure-sensitive adhesive layer described above.
The above-mentioned "thickness of the curable resin layer" is a value represented by the average of the thickness measured by a contact type thickness gauge at any five points. If it is difficult to apply the contact-type thickness gauge directly to the pressure-sensitive adhesive layer, the same as above may be applied in a state where other layers such as a base film, a pressure-sensitive adhesive layer, and a release material described later are laminated. By measuring the total thickness of the film and taking the difference from the thickness of the other layers (measured by the same method as above or the measurement method of the adhesive layer described above). It may be calculated.

The curable resin layer preferably has pressure-sensitive adhesiveness, preferably has heat-curable property, and more preferably has both pressure-sensitive adhesiveness and heat-curable property. The curable resin layer having both pressure-sensitive adhesiveness and thermosetting property can be attached by lightly pressing against various adherends in an uncured state. Further, the curable resin layer may be one that can be attached to various adherends by heating and softening. The curable resin layer undergoes thermosetting and finally becomes a cured product having high impact resistance, and the cured product has excellent shear strength and retains sufficient adhesive properties even under severe high temperature and high humidity conditions. obtain.

(Polymer component (a))
The polymer component (a) is a polymer compound for imparting film-forming property, flexibility, etc. to the curable resin layer.
Polymer component (a) may be used alone or in combination of two or more thereof.

As the polymer component (a), an acrylic resin, a polyester resin, a urethane resin, an acrylic urethane resin, a silicone resin, a rubber polymer, a phenoxy resin or the like can be used, but an acrylic resin is preferable.

As the acrylic resin, a known acrylic polymer can be used.
The weight average molecular weight (Mw) of the acrylic resin is preferably 10,000 to 2 million, more preferably 100,000 to 1.5 million. If the weight average molecular weight of the acrylic resin is too small, the adhesive force between the curable resin layer and the pressure-sensitive adhesive layer becomes high, which may cause poor pickup of the semiconductor chip. Further, if the weight average molecular weight of the acrylic resin is too large, the curable resin layer may not be able to follow the uneven surface of the adherend, which may cause voids and the like.
In the present specification, the weight average molecular weight is a polystyrene-equivalent value measured by a gel permeation chromatography (GPC) method unless otherwise specified.

The glass transition temperature (Tg) of the acrylic resin is preferably -60 to 70 ° C, more preferably -30 to 50 ° C. If the Tg of the acrylic resin is too low, the peeling force between the curable resin layer and the pressure-sensitive adhesive layer becomes large, and a semiconductor chip pickup failure may occur. Further, if the Tg of the acrylic resin is too high, the adhesive force for fixing the semiconductor wafer may be insufficient.

Examples of the monomers constituting the acrylic resin include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, and n-. Octyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate (lauryl (meth) acrylate), tridecyl (meth) acrylate , Tetradecyl (meth) acrylate (myristyl (meth) acrylate), pentadecyl (meth) acrylate, hexadecyl (meth) acrylate (palmityl (meth) acrylate), heptadecyl (meth) acrylate, octadecyl (meth) acrylate (stearyl (meth) acrylate) ), Etc., an alkyl (meth) acrylate having a chain-like alkyl group and 1 to 18 carbon atoms;
Cycloalkyl (meth) acrylate, benzyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, imide (meth) (Meta) acrylate having a cyclic skeleton such as acrylate;
Hydroxyl-containing (meth) acrylates such as hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate;
Examples thereof include (meth) acrylic acid esters such as glycidyl group-containing (meth) acrylates such as glycidyl (meth) acrylates.
Further, the acrylic resin may be one obtained by polymerizing a monomer such as acrylic acid, methacrylic acid, itaconic acid, vinyl acetate, acrylonitrile, styrene, or N-methylolacrylamide.
The monomer constituting the acrylic resin may be only one kind or two or more kinds.
In the present specification, the term "polymer" or "resin" or the like used for a substance in which a monomer is polymerized is a "polymer" or a "polymer" composed of a structural unit (also referred to as a repeating unit) derived from the monomer. It means "resin" or the like. Further, in the present specification, when the amount of the monomer used in the production of the "polymer" or the "resin" is described by the ratio of the mass, the number of moles, etc., the ratio is the said monomer. Can be read as the ratio of the structural units derived from the monomer to the total amount of the polymerized "polymer" or "resin". That is, for example, when it is explained that the monomers X and Y are used in an amount of 20% by mass and 80% by mass, respectively, and polymerized to obtain a polymer Z, in such a polymer Z, the polymer Z It can be read that the ratio of the structural unit derived from the monomer X and the structural unit derived from the monomer Y to the total mass is 20% by mass and 80% by mass, respectively.

The acrylic resin may have a functional group capable of binding to other compounds such as a vinyl group, a (meth) acryloyl group, an amino group, a hydroxyl group, a carboxyl group and an isocyanate group. The bonding with the other compound may be carried out via a cross-linking agent (f) described later, or the functional group may be directly bonded to the other compound without using the cross-linking agent (f). .. When the acrylic resin is bonded by these functional groups, the package reliability of the semiconductor device using the work fixing sheet with the resin layer tends to be improved.

When the curable resin composition contains an acrylic resin as the polymer component (a), the content of the acrylic resin in the curable resin composition is 50 with respect to the total solid content of the curable resin composition. It is preferably mass% or more. Within such a range, the curable resin layer has preferable properties when the curable resin layer is used in a process of collectively curing the semiconductor chip at the time of resin sealing. This is because, in such a process, wire bonding to the chip is performed before the resin is sealed in the semiconductor chip, but even when the curable resin layer before curing is exposed to a high temperature, it has a certain degree of hardness. This is because wire bonding can be performed in a state where the above is maintained. That is, when the content of the acrylic resin in the curable resin composition is relatively large, the storage elastic modulus of the curable resin layer can be increased even before thermosetting. Therefore, even when the curable resin layer is uncured or semi-cured, vibration and displacement of the chip during wire bonding are suppressed, and wire bonding can be performed stably.
Further, when the curable resin composition contains an acrylic resin as the polymer component (a), the content of the acrylic resin in the curable resin composition is the total amount of the solid content of the curable resin composition. On the other hand, it is more preferably 50 to 90% by mass. When the content of the acrylic resin is relatively large as described above, the adhesiveness between the pressure-sensitive adhesive layer and the curable resin layer tends to be high, and the adhesive strength tends to be high. However, the pressure-sensitive adhesive layer in the present invention is used. By using the adhesive layer, the adhesive force between the pressure-sensitive adhesive layer and the curable resin layer is reduced, and the ease of picking up the semiconductor chip is improved.
As described above, when the curable resin layer contains an acrylic resin as the polymer component (a), the content of the acrylic resin in the curable resin layer is preferably 50% by mass or more, preferably 50. More preferably, it is ~ 90% by mass.

In the present invention, the peelability of the work fixing sheet (adhesive layer) described above from the curable resin layer is improved to improve the pick-up property, and the curable resin layer on the uneven surface of the adherend is provided. In order to suppress the generation of voids and the like by following, even if a thermoplastic resin other than the acrylic resin (hereinafter, may be simply abbreviated as "thermoplastic resin") is used alone as the polymer component (a). Alternatively, it may be used in combination with an acrylic resin.
The thermoplastic resin preferably has a weight average molecular weight of 10 to 100,000, and more preferably 3000 to 80,000.
The glass transition temperature (Tg) of the thermoplastic resin is preferably -30 to 150 ° C, more preferably -20 to 120 ° C.
Examples of the thermoplastic resin include polyester resin, urethane resin, phenoxy resin, polybutene, polybutadiene, polystyrene and the like.
As the thermoplastic resin, one of the above may be used alone, or two or more thereof may be used in combination.

While the above-mentioned effects can be obtained by using the thermoplastic resin, the hardness of the curable resin layer before curing is reduced when exposed to a high temperature, and the curable resin is in an uncured or semi-cured state. There is a concern that the wire bonding suitability of the layer may decrease. Therefore, it is preferable to set the content of the acrylic resin in the curable resin composition in consideration of such an influence.
In the present invention, it is preferable to use the thermoplastic resin in combination with an acrylic resin.

(Curable component (b))
Examples of the curable component (b) include epoxy-based thermosetting resins, thermosetting polyimide resins, urethane resins, unsaturated polyester resins, and silicone resins. Among these, epoxy-based thermosetting resins are preferable .

-Epoxy-based thermosetting resin The epoxy-based thermosetting resin is composed of an epoxy resin and a thermosetting agent.
One type of epoxy thermosetting resin may be used alone, or two or more types may be used in combination.

Examples of the epoxy resin include known ones, and specific examples thereof include a polyfunctional epoxy resin, a biphenyl compound, a bisphenol A diglycidyl ether and its hydrogenated product, an orthocresol novolac epoxy resin, and a dicyclopentadiene type epoxy resin. , Biphenyl type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenylene skeleton type epoxy resin, and other bifunctional or higher functional epoxy compounds can be exemplified.

Further, as the epoxy resin, an epoxy resin having an unsaturated hydrocarbon group may be used. Examples of the epoxy resin having an unsaturated hydrocarbon group include a compound obtained by converting a part of the epoxy resin of the polyfunctional epoxy resin into a group containing an unsaturated hydrocarbon group. Such a compound can be produced, for example, by adding acrylic acid to an epoxy group. Further, examples of the epoxy resin having an unsaturated hydrocarbon group include a compound in which a group containing an unsaturated hydrocarbon group is directly bonded to an aromatic ring or the like constituting the epoxy resin. The unsaturated hydrocarbon group is a polymerizable unsaturated group, and specifically, an ethenyl group (vinyl group), a 2-propenyl group (allyl group), an acryloyl group, a methacryloyl group, an acrylamide group, and a methacrylamide. A group and the like can be exemplified, and an acryloyl group is preferable.
Epoxy resins having unsaturated hydrocarbon groups have higher compatibility with acrylic resins than epoxy resins having no unsaturated hydrocarbon groups. Therefore, by using a curable resin composition containing an epoxy resin having an unsaturated hydrocarbon group, the package reliability of the semiconductor device is improved.

The epoxy resin preferably has a high softening point or glass transition temperature from the viewpoint of improving easy pick-up property.

The number average molecular weight of the epoxy resin is not particularly limited, but is preferably 300 to 30,000, more preferably 400 to 10,000, from the viewpoint of curability of the curable resin layer, strength after curing, and heat resistance. It is preferably 500 to 3000, and particularly preferably 500 to 3000.
The epoxy equivalent of the epoxy resin is preferably 100 to 1000 g / eq, more preferably 300 to 800 g / eq.

One type of the epoxy resin may be used alone, or two or more types may be used in combination.

The thermosetting agent functions as a curing agent for the epoxy resin.
Examples of the thermosetting agent include compounds having two or more functional groups capable of reacting with epoxy groups in one molecule. Examples of the functional group include a phenolic hydroxyl group, an alcoholic hydroxyl group, an amino group, a carboxyl group, and a group in which an acid group is annealed, and a group in which a phenolic hydroxyl group, an amino group, and an acid group are annealed. It is preferably present, more preferably a phenolic hydroxyl group or an amino group, and particularly preferably a phenolic hydroxyl group.

Among the above-mentioned heat-curing agents, examples of the phenol-based curing agent (curing agent having a phenolic hydroxyl group) include polyfunctional phenol resin, biphenol, novolak-type phenol resin, dicyclopentadiene-based phenol resin, and aralkylphenol resin. ..
Among the thermosetting agents, examples of amine-based curing agents (curing agents having an amino group) include DICY (dicyandiamide).

The thermosetting agent may have an unsaturated hydrocarbon group.
As a thermosetting agent having an unsaturated hydrocarbon group, a compound formed by substituting a part of the hydroxyl groups of the phenol resin with a group containing an unsaturated hydrocarbon group, and an unsaturated hydrocarbon group on the aromatic ring of the phenol resin. Examples thereof include compounds in which the containing groups are directly bonded. The unsaturated hydrocarbon group in the thermosetting agent is the same as the unsaturated hydrocarbon group in the epoxy resin having the unsaturated hydrocarbon group described above.

The thermosetting agent preferably has a high softening point or glass transition temperature from the viewpoint of improving easy pick-up property.

The number average molecular weight of the thermosetting agent is preferably 300 to 30,000, more preferably 400 to 10,000, and particularly preferably 500 to 3,000.

The thermosetting agent may be used alone or in combination of two or more.

The content of the thermosetting agent in the curable resin composition is preferably 0.1 to 500 parts by mass, more preferably 1 to 200 parts by mass, based on 100 parts by mass of the epoxy resin content. preferable. If the content of the thermosetting agent is too small, adhesiveness may not be obtained due to insufficient curing, and if the content of the thermosetting agent is excessive, the moisture absorption rate of the curable resin layer increases, and the package reliability. May decrease.

The content of the curable component (b) of the curable resin composition (curable resin layer) is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the content of the polymer component (a). It is more preferably 1.5 to 75 parts by mass, and particularly preferably 2 to 60 parts by mass. When the content of the curable component (b) is in the above range, the hardness of the curable resin layer before curing tends to be maintained, and the curable resin layer in an uncured or semi-cured state tends to be maintained. Wire bonding suitability is improved. On the other hand, when the content of the curable component (b) is relatively small with respect to the content of the polymer component (a), each component of the curable component (b) has a high softening point and a high glass transition temperature. As a matter of fact, even if it is attempted to suppress the increase in the adhesive force between the pressure-sensitive adhesive layer and the curable resin layer and improve the easy pick-up property, it may not be sufficiently improved. However, by using the pressure-sensitive adhesive layer in the present invention, the adhesive force between the pressure-sensitive adhesive layer and the curable resin layer is reduced, and the ease of picking up the semiconductor chip is improved.

The curable resin layer is a curable resin that contains, if necessary, other components that do not correspond to the polymer component (a) and the curable component (b) in order to improve its various physical properties. It may be formed by using the composition.
Examples of other components contained in the curable resin composition include a filler (c), a curing accelerator (d), a coupling agent (e), a cross-linking agent (f), and a general-purpose additive (g). ..

(Filler (c))
The curable resin composition usually contains the filler (c), so that the coefficient of thermal expansion thereof can be easily adjusted. Therefore, by using such a curable resin composition, the coefficient of thermal expansion of the curable resin layer after curing is optimized for the semiconductor chip, metal, or organic substrate to improve the package reliability. Can be done.
Further, usually, by using the curable resin composition containing the filler (c), the hygroscopicity of the curable resin layer after curing can be reduced.
The filler (c) is a component that does not correspond to either the polymer component (a) or the curable component (b).

However, in the present invention, as described above, the curable resin layer does not contain the filler (c), or the content of the filler (c) is more than 0% by mass and 5% by mass. Therefore, the content of the filler (c) of the curable resin composition is less than 5% by mass, preferably less than 3% by mass, based on the total solid content of the curable resin composition. It is preferably less than 1% by mass.

The filler (c) is preferably an inorganic filler (c), and preferred inorganic fillers are powders of silica, alumina, talc, calcium carbonate, titanium white, red iron oxide, silicon carbide, boron nitride and the like; Spherical beads such as silica; single crystal fibers such as these silica; glass fibers and the like can be exemplified.
Among these, the inorganic filler is preferably a silica filler or an alumina filler.
As the inorganic filler (c), one type may be used alone, or two or more types may be used in combination.

(Curing accelerator (d))
The curing accelerator (d) is used to adjust the curing rate of the curable resin composition, and is a component that does not correspond to either the polymer component (a) or the curable component (b).
Preferred curing accelerators (d) include tertiary amines such as triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol and tris (dimethylaminomethyl) phenol; 2-methylimidazole, 2-phenylimidazole, 2 Imidazoles such as −phenyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole (one or more hydrogen atoms are groups other than hydrogen atoms). (Imidazole substituted with); organic phosphines such as tributylphosphine, diphenylphosphine, triphenylphosphine (phosphine in which one or more hydrogen atoms are substituted with an organic group); tetraphenylphosphonium tetraphenylborate, triphenylphosphine tetraphenyl Examples thereof include tetraphenylborone salts such as borate.
As the curing accelerator (d), one type may be used alone, or two or more types may be used in combination.

When the curing accelerator (d) is used, the content of the curing accelerator (d) in the curable resin composition is 0.01 to 10 parts by mass with respect to 100 parts by mass of the content of the curable component (b). It is preferably 0.1 to 1 part by mass, and more preferably 0.1 to 1 part by mass. When the content of the curing accelerator (d) is in such a range, the curable resin layer has excellent adhesive properties even under high temperature and high humidity conditions, and is exposed to severe reflow conditions. However, high package reliability can be achieved. If the content of the curing accelerator (d) is too small, the effect of using the curing accelerator (d) cannot be sufficiently obtained, and if the content of the curing accelerator (d) is excessive, the polarity is high. The curing accelerator (d) of No. 1 moves to the adhesion interface side with the adherend in the curable resin layer under high temperature and high humidity conditions and segregates, thereby lowering the reliability of the package.

(Coupling agent (e))
By using a coupling agent (e) having a functional group that reacts with an inorganic compound and a functional group that reacts with an organic functional group, the adhesiveness and adhesion of the curable resin layer to the adherend are improved. Can be done. Further, by using the coupling agent (e), the water resistance of the cured product obtained by curing the curable resin layer can be improved without impairing the heat resistance thereof.
The coupling agent (e) is a component that does not correspond to either the polymer component (a) or the curable component (b).

The coupling agent (e) is preferably a compound having a functional group that reacts with the functional group of the polymer component (a), the curable component (b), and the like, and is preferably a silane coupling agent.
Preferred silane coupling agents include γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and γ- (methacryloxy). Propyl) trimethoxysilane, γ-aminopropyltrimethoxysilane, N-6- (aminoethyl) -γ-aminopropyltrimethoxysilane, N-6- (aminoethyl) -γ-aminopropylmethyldiethoxysilane, N -Phenyl-γ-aminopropyltrimethoxysilane, γ-ureidopropyltriethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, bis (3-triethoxysilylpropyl) tetrasulfan, methyltri Examples thereof include methoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriacetoxysilane, and imidazolesilane.
As the coupling agent (e), one of the above may be used alone, or two or more of the above may be used in combination.

When the coupling agent (e) is used, the content of the coupling agent (e) in the curable resin composition is 100 parts by mass of the total content of the polymer component (a) and the curable component (b). , 0.03 to 20 parts by mass, more preferably 0.05 to 10 parts by mass, and particularly preferably 0.1 to 5 parts by mass. If the content of the coupling agent (e) is too small, the above-mentioned effect due to the use of the coupling agent (e) may not be obtained, while the content of the coupling agent (e) is too large. And, outgas may occur.

(Crosslinking agent (f))
When the above-mentioned acrylic resin having a functional group capable of binding to a functional group of another compound such as an isocyanate group is used as the polymer component (a), this functional group is bonded to another compound and crosslinked. Therefore, a cross-linking agent (f) can be used. By cross-linking with the cross-linking agent (f) as described above, the initial adhesive force and cohesive force of the curable resin layer can be adjusted.
Examples of the cross-linking agent (f) include an organic polyvalent isocyanate compound and an organic polyvalent imine compound.
The cross-linking agent (f) is a component that does not correspond to either the polymer component (a) or the curable component (b).

Examples of the organic polyvalent isocyanate compound include aromatic polyvalent isocyanate compounds, aliphatic polyvalent isocyanate compounds, alicyclic polyvalent isocyanate compounds, and trimerics, isocyanurates and adducts (ethylene glycol, propylene glycol) of these compounds. , Neopentyl glycol, trimethylolpropane, reaction product with low molecular weight active hydrogen-containing compound such as castor oil, for example, trimethylolpropane adductoxylylene diisocyanate), or organic polyvalent isocyanate compound and polyol compound. Examples thereof include the obtained terminal isocyanate urethane prepolymer.

More specifically, as the organic polyvalent isocyanate compound, 2,4-tolylene diisocyanate; 2,6-tolylene diisocyanate; 1,3-xylylene diisocyanate; 1,4-xylene diisocyanate; diphenylmethane-4,4 ′ -Diisocyanate; diphenylmethane-2,4'-diisocyanate; 3-methyldiphenylmethane diisocyanate; hexamethylene diisocyanate; isophorone diisocyanate; dicyclohexylmethane-4,4'-diisocyanate; dicyclohexylmethane-2,4'-diisocyanate; trimethylolpropane, etc. A compound in which either one or both of tolylene diisocyanate and hexamethylene diisocyanate is added to all or a part of the hydroxyl groups of the polyol; lysine diisocyanate and the like can be exemplified.

Examples of the organic polyvalent imine compound include N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxyamide), trimethylolpropane-tri-β-aziridinyl propionate, and tetramethylolmethane-tri. Examples thereof include -β-aziridinyl propionate, N, N'-toluene-2,4-bis (1-aziridinecarboxyamide) triethylene melamine and the like.

When an isocyanate-based cross-linking agent is used as the cross-linking agent (f), it is preferable to use a hydroxyl group-containing polymer as the acrylic resin as the polymer component (a). When the cross-linking agent (f) has an isocyanate group and the acrylic resin has a hydroxyl group, the cross-linked structure can be easily introduced into the curable resin layer by the reaction between the cross-linking agent (f) and the acrylic resin.

When the cross-linking agent (f) is used, the content of the cross-linking agent (f) in the curable resin composition is 0.01 to 20 parts by mass with respect to 100 parts by mass of the content of the polymer component (a). It is preferably 0.1 to 10 parts by mass, and particularly preferably 0.5 to 5 parts by mass.

(General-purpose additive (g))
Examples of the general-purpose additive (g) include known plasticizers, antistatic agents, antioxidants, pigments, dyes, gettering agents and the like.
The general-purpose additive (g) is a component that does not correspond to either the polymer component (a) or the curable component (b).

(solvent)
The curable resin composition preferably further contains a solvent in order to improve the handleability by dilution.
The solvent contained in the curable resin composition may be the same as the solvent in the pressure-sensitive adhesive composition described above.
The solvent contained in the curable resin composition may be only one kind or two or more kinds.
The solvent contained in the curable resin composition is preferably methyl ethyl ketone or the like from the viewpoint of uniformly mixing each component used in the curable resin composition.
The solvent is a component that does not correspond to either the polymer component (a) or the curable component (b).

As described above, the total content of the polymer component (a) and the curable component (b) of the curable resin layer is 95% by mass or more, and 97% by mass or more, based on the total amount of the curable resin layer. Is more preferable, and 98% by mass or more is further preferable. Then, in order to form such a curable resin layer, the total contents of the polymer component (a) and the curable component (b) of the curable resin composition are other than the solvent in the curable resin composition. It is 95% by mass or more, more preferably 97% by mass or more, and further preferably 98% by mass or more, based on the total amount of all the components of the above.
Further, the total content of the polymer component (a) and the curable component (b) in the curable resin layer may be 100% by mass with respect to the total amount of the curable resin layer.

The curable resin composition can be obtained by blending the above-mentioned components for constituting the curable resin composition. For example, the curable resin composition can be obtained by the same method as in the case of the above-mentioned pressure-sensitive adhesive composition except that the blending components are different. ..
When a solvent is used, the solvent may be mixed with any compounding component other than the solvent and diluted in advance, or any compounding component other than the solvent may be diluted in advance. You may use it by mixing the solvent with these compounding components without leaving.

The ease of picking up the semiconductor chip described in the work fixing sheet with a resin layer according to the present invention is, for example, the speed at which the semiconductor chip on the surface of the work fixing sheet with a resin layer is pushed up by a commercially available die bonder. And the push-up height is set to a predetermined condition, and it is possible to evaluate whether or not the semiconductor chip can be picked up under this condition. At this time, for example, when a total of 100 chips are continuously picked up and all the chips are successfully picked up, or after one or more chips are successfully picked up, the second and subsequent chips are picked up. When any of the above pickups fails, it can be determined that the easy pickup property is relatively good.

<Manufacturing method of work fixing sheet with resin layer>
In the work fixing sheet with a resin layer according to the present invention, for example, a pressure-sensitive adhesive layer is formed on a base film using the pressure-sensitive adhesive composition, and the pressure-sensitive adhesive layer is cured by using the curable resin composition. It can be manufactured by forming a sex resin layer.

The pressure-sensitive adhesive layer can be formed by applying the pressure-sensitive adhesive composition to the surface of the base film (the surface 11a of the base film 11 in FIG. 1) and drying it. At this time, if necessary, the applied pressure-sensitive adhesive composition may be crosslinked by heating. The heating conditions can be, for example, 100 to 130 ° C. for 1 to 5 minutes, but are not limited thereto. Further, the pressure-sensitive adhesive layer can also be formed by applying the pressure-sensitive adhesive composition to the surface of the peel-off layer of the release material and drying it to bond the pressure-sensitive adhesive layer to the surface of the base film and removing the release material. ..

The pressure-sensitive adhesive composition may be applied to the surface of the base film or the surface of the release layer of the release material by a known method, and may be performed by an air knife coater, a blade coater, a bar coater, a gravure coater, a roll coater, a roll knife coater, etc. Examples thereof include methods using various coaters such as curtain coaters, die coaters, knife coaters, screen coaters, Meyer bar coaters, and kiss coaters.

The curable resin layer can be formed by using the curable resin composition in the same manner as when the pressure-sensitive adhesive layer is formed on the base film as described above, but usually, the curable resin layer is curable on the pressure-sensitive adhesive layer. It is difficult to apply the resin composition directly. Therefore, for example, the curable resin composition formed by applying a curable resin composition to the surface of the release layer of the release material and drying it is attached to the surface of the pressure-sensitive adhesive layer, and the release material is removed. A method in which a resin layer is separately formed and this is attached to the surface of the pressure-sensitive adhesive layer is preferable.

Further, in the work fixing sheet with a resin layer according to the present invention, in addition to the above method, for example, a pressure-sensitive adhesive layer is formed by using the pressure-sensitive adhesive composition, and a curable resin is used by using the curable resin composition. After forming the layers, the pressure-sensitive adhesive layer and the curable resin layer are laminated to form a laminated body, and the base film can be bonded to the surface of the pressure-sensitive adhesive layer of the laminated body.
The conditions for forming the pressure-sensitive adhesive layer and the curable resin layer in this case are the same as those described above.

Hereinafter, the present invention will be described in more detail with reference to specific examples. However, the present invention is not limited to the examples shown below.

<Manufacturing of workpiece fixing sheet with resin layer>
[Example 1]
A work fixing sheet with a resin layer having the configuration shown in FIG. 1 was manufactured. More specifically, it is as follows.

(Manufacture of acrylic acid alkyl ester polymer)
In a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer, 80 parts by mass of lauryl acrylate (hereinafter abbreviated as "LA") and -2-hydroxyethyl acrylate (hereinafter "HEA") (Abbreviated) (20 parts by mass), benzoyl peroxide (0.2 parts by mass), ethyl acetate (70 parts by mass), and toluene (30 parts by mass) are added, and a polymerization reaction is carried out at 60 ° C. for 8 hours in a nitrogen stream. As a result, an acrylic polymer (A) was obtained. The compounding ratio of each component is shown in Table 1 below.
To this acrylic polymer (A), 2-methacryloyloxyethyl isocyanate (hereinafter abbreviated as "MOI") (22 parts by mass, about 80 mol% with respect to HEA) and dibutyltin laurylate (hereinafter, "DBTL") (Abbreviation) (0.13 parts by mass) is added, and the addition reaction is carried out at 23 ° C. for 12 hours in an air stream to bring the target acrylic acid alkyl ester polymer (A-1) into a 47% by mass solution. I got it in. The compounding ratio of each component is shown in Table 1 below.

(Manufacturing of adhesive composition)
Photopolymerization initiator (Z-1) (“Irgacure 651” manufactured by Ciba Specialty Chemicals, Inc., benzyl dimethyl ketal) with respect to the acrylic acid alkyl ester polymer (A-1) (100 parts by mass) obtained above. ) (3 parts by mass), acetylacetone (1 part by mass) as a reaction retardant, dilute with methyl ethyl ketone, stir well, and then trimethyl propane as an isocyanate-based cross-linking agent (B-1). The isocyanate group contained in the isocyanate trimer adduct (“Coronate L” manufactured by Nippon Polyurethane Co., Ltd.) (7.5 parts by mass, 1 mol of residual hydroxyl group in the acrylic acid ester polymer (A-1)) An amount of 1 mol) was added and the mixture was stirred at 23 ° C. to obtain a pressure-sensitive adhesive composition having a solid content concentration of 25% by mass. The number of copies to be blended in this "manufacturing of the pressure-sensitive adhesive composition" is a solid content conversion value. The compounding ratio of each component is shown in Table 1 below.

(Manufacturing of work fixing sheet)
The pressure-sensitive adhesive composition obtained above was applied onto the silicone-treated peeling surface of a polyethylene terephthalate (PET) release liner and dried by heating at 120 ° C. for 2 minutes to form a pressure-sensitive adhesive layer having a thickness of 10 μm. .. Next, an ethylene-methacrylic acid polymer film having a thickness of 100 μm as a base film was attached to the surface of the pressure-sensitive adhesive layer and stored at 23 ° C. for 168 hours to obtain a work fixing sheet.

(Manufacturing of curable resin composition)
Acrylic resin (“SG-P3” manufactured by Nagase ChemteX Corporation) (87.8 parts by mass), epoxy resin (“NC-3000” manufactured by Nippon Kayaku Co., Ltd.) (12 parts by mass), phenol resin (manufactured by Meiwa Kasei Co., Ltd.) "MEH-7851-H") (10 parts by mass), triphenylphosphine as a curing accelerator (0.2 parts by mass), and a silane coupling agent ("KBM403" manufactured by Shinetsu Silicone Co., Ltd., 3-glycidoxypropyl). Trimethoxysilane (1 part by mass) was dissolved in methyl ethyl ketone to obtain a methyl ethyl ketone solution having a solid content concentration of 20% by mass as a curable resin composition.

(Manufacturing of workpiece fixing sheet with resin layer)
The curable resin composition obtained above was applied onto a release liner (“SP-PET38131” manufactured by Lintec Corporation) and dried at 100 ° C. for 1 minute to form a curable resin layer having a thickness of 20 μm. Further, a release liner of the same type as above was attached to the curable resin layer. Then, after making a half cut into a circle having a diameter of 150 mm so as to cut the bonded release liner and the curable resin layer, unnecessary portions on the outside of the circle were removed. Then, the release liner was removed from the work fixing sheet obtained above. Further, the release liner that was half-cut together was removed from the curable resin layer, and the adhesive layer of the work fixing sheet was bonded to the surface of the curable resin layer to obtain a work fixing sheet with a resin layer.

<Evaluation of work fixing sheet with resin layer>
The work fixing sheet with the resin layer obtained above was evaluated for easy pick-up by the following method.

(Easy pickup)
Using a tape mounter (“Adwill RAD2500” manufactured by Lintec Corporation), the work fixing sheet with the resin layer obtained above was attached to the 2000th polished surface of a silicon wafer (150 mm diameter, thickness 100 μm) at 60 ° C. Next, after fixing this to a ring frame for wafer dicing, a silicon wafer was diced to a size of 10 mm × 10 mm using a dicing device (“DFD651” manufactured by Disco Corporation) to obtain chips. At the time of this dicing, the base film was cut by 20 μm from the surface. Next, using an ultraviolet irradiation device (“Adwill RAD2000” manufactured by Lintec Corporation), ultraviolet rays were irradiated to the work fixing sheet with the resin layer from the base film side under the conditions of 220 mW / cm ² and 190 mJ / cm ² . Next, using a die bonder (“BESTEM-D02” manufactured by Canon Machinery Co., Ltd.), the needle pushing speed was set to 1 mm / s, and it was evaluated whether or not the tip could be picked up when the pushing height was 0.2 mm. The needles were arranged in 8 mm square and 4 pins. The evaluation is performed by continuously picking up 100 chips, and if all the chips are successfully picked up, "A" is given, and after one or more chips are successfully picked up, the second and subsequent chips are evaluated. The case where one of the above pickups failed was evaluated as "A1", and the case where the first chip failed was evaluated as "B". The results are shown in Table 1 below.

<Manufacturing and evaluation of workpiece fixing sheet with resin layer>
[Example 2, Comparative Examples 1 and 2, Reference Example 1]
A work fixing sheet with a resin layer was produced in the same manner as in Example 1 except that the compounding components at the time of producing the acrylic acid alkyl ester polymer and the compounding components at the time of producing the curable resin composition were as shown in Table 1 below. And evaluated. The results are shown in Table 1 below.
The acrylic acid alkyl ester polymers obtained here are the acrylic acid alkyl ester polymer (A-2) (Example 2) and the acrylic acid alkyl ester polymer (R-1) (Comparative Example 1), respectively. , Acrylic acid alkyl ester polymer (R-2) (Comparative Example 2, Reference Example 1).
Further, in all the examples, comparative examples and reference examples, the pressure-sensitive adhesive composition adjusts the amount of methyl ethyl ketone to adjust the solid content concentration to 25% by mass.

In Table 1 below, "2EHA" means 2-ethylhexyl acrylate, "ISTA" means isostearyl acrylate, and "MA" means methyl acrylate.
The "filler" is "SC2050MA" manufactured by Admatex.
In addition, "-" in the column of compounded components means that this component is not compounded.

As shown in Table 1, the work fixing sheet with the resin layer of Examples 1 and 2 is used for producing alkyl acrylate polymers (the polymers (A-1) and (A-2)) with an alkyl acrylate. LA (alkyl group has 12 carbon atoms) or ISTA (alkyl group carbon number 18) is used as the ester, and the total content of the polymer component (a) and the curable component (b) of the curable resin layer is determined. It was 98.9% by mass and had an easy pick-up property.
On the other hand, the work fixing sheet with the resin layer of Comparative Examples 1 and 2 was used as an acrylic acid alkyl ester for the production of the acrylic acid alkyl ester polymer (the polymers (R-1) and (R-2)). , MA (the number of carbon atoms of the alkyl group is 1) or 2EHA (the number of carbon atoms of the alkyl group is 8) was used, and it did not have easy pick-up property.
In the work fixing sheet with a resin layer of Reference Example 1, MA was used as the acrylic acid alkyl ester in the production of the acrylic acid alkyl ester polymer, but the curable resin layer contained a filler and was easily picked up. Had sex.
As shown in Table 1, in each of the above examples, after the pickup of one or more chips succeeds, the pickup of any of the second and subsequent chips fails, that is, the easy pick-up property. There were no examples that could be evaluated as "A1".

The present invention can be used for manufacturing semiconductor chips and the like.

1 ... Work fixing sheet, 10 ... Work fixing sheet with resin layer, 11 ... Base film, 11a ... Base film surface, 12 ... Adhesive layer, 12a ... Adhesive Surface of agent layer, 13 ... Curable resin layer, 13a ... Surface of curable resin layer, 14 ... Release film

Claims (4)

A work fixing sheet with a resin layer having an adhesive layer on a base film and a curable resin layer on the adhesive layer.
The pressure-sensitive adhesive layer contains a (meth) acrylic acid alkyl ester polymer obtained by polymerizing a monomer containing a (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms in the alkyl group.
In the (meth) acrylic acid alkyl ester polymer, the ratio of the (meth) acrylic acid alkyl ester having 10 to 18 carbon atoms of the alkyl group to the total mass of all the monomers used for the polymerization is , 70% by mass or more,
The curable resin layer contains a polymer component (a) and a curable component (b).
The total content of the polymer component (a) and the curable component (b) of the curable resin layer is 95% by mass or more with respect to the total amount of the curable resin layer.
The polymer component (a) is an acrylic resin, a polyester resin (excluding unsaturated polyester resin), an acrylic urethane resin, a rubber polymer, or a phenoxy resin.
A work fixing sheet with a resin layer, wherein the curable component (b) is an epoxy-based thermosetting resin, a thermosetting polyimide resin, a urethane resin, an unsaturated polyester resin, or a silicone resin. The curable resin layer further contains a coupling agent (e),
The content of the coupling agent (e) in the curable resin layer is 0.1 to 5 parts by mass with respect to 100 parts by mass of the total contents of the polymer component (a) and the curable component (b). The work fixing sheet with a resin layer according to claim 1, wherein the work fixing sheet is characterized by the above. The curable resin layer contains an acrylic resin as the polymer component (a).
The work fixing sheet with a resin layer according to claim 1 or 2 , wherein the content of the acrylic resin with respect to the total amount of solids in the curable resin layer is 50% by mass or more. Claim 1 is characterized in that the content of the curable component (b) of the curable resin layer is 1 to 100 parts by mass with respect to 100 parts by mass of the content of the polymer component (a). The work fixing sheet with a resin layer according to any one of 3 to 3 .

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