WO2010143510A1 - 接着剤組成物 - Google Patents
接着剤組成物 Download PDFInfo
- Publication number
- WO2010143510A1 WO2010143510A1 PCT/JP2010/058558 JP2010058558W WO2010143510A1 WO 2010143510 A1 WO2010143510 A1 WO 2010143510A1 JP 2010058558 W JP2010058558 W JP 2010058558W WO 2010143510 A1 WO2010143510 A1 WO 2010143510A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- adhesive composition
- substrate
- monomer
- solvent
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 48
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 239000011347 resin Substances 0.000 claims abstract description 118
- 229920005989 resin Polymers 0.000 claims abstract description 118
- 239000000178 monomer Substances 0.000 claims abstract description 39
- 239000012790 adhesive layer Substances 0.000 claims abstract description 28
- 239000000758 substrate Substances 0.000 claims abstract description 25
- 150000003505 terpenes Chemical class 0.000 claims abstract description 25
- 235000007586 terpenes Nutrition 0.000 claims abstract description 25
- 150000001925 cycloalkenes Chemical class 0.000 claims abstract description 15
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 13
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 13
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
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- 238000002156 mixing Methods 0.000 claims description 3
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- 229930007646 carveol Natural products 0.000 description 1
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- WPGPCDVQHXOMQP-UHFFFAOYSA-N carvotanacetone Natural products CC(C)C1CC=C(C)C(=O)C1 WPGPCDVQHXOMQP-UHFFFAOYSA-N 0.000 description 1
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- RFFOTVCVTJUTAD-UHFFFAOYSA-N cineole Natural products C1CC2(C)CCC1(C(C)C)O2 RFFOTVCVTJUTAD-UHFFFAOYSA-N 0.000 description 1
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- AZOCECCLWFDTAP-RKDXNWHRSA-N dihydrocarvone Natural products C[C@@H]1CC[C@@H](C(C)=C)CC1=O AZOCECCLWFDTAP-RKDXNWHRSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
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- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J145/00—Adhesives based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/06—Waxes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
-
- 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
- H01L21/18—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 the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
Definitions
- the present invention relates to an adhesive composition, and more specifically, an adhesive composition for temporarily fixing the substrate and a support such as a glass plate or a film when processing a substrate such as a semiconductor wafer. About.
- a thin semiconductor silicon chip for example, a high-purity silicon single crystal or the like is sliced into a wafer, and a predetermined circuit pattern is formed on the wafer surface using a photoresist. Next, after grinding the back surface of the obtained semiconductor wafer, the semiconductor wafer ground to a predetermined thickness is diced to obtain chips.
- the thinned wafer itself is fragile and easily damaged, so it is necessary to reinforce it.
- the circuit pattern formed on the wafer surface from being contaminated by, for example, polishing dust generated by grinding. Therefore, the following methods are known as methods for preventing damage to the wafer and protecting the circuit pattern on the wafer surface.
- Patent Documents 1 and 2 A method in which a support is temporarily fixed to a wafer with an adhesive layer, and then ground.
- Patent Documents 3 and 4 A technique in which an adhesive film provided with an adhesive layer is affixed to the circuit pattern surface on the wafer surface, and then the adhesive film is peeled off.
- the adhesive layer support or pressure-sensitive adhesive film
- a peeling defect such as a residue remains at the time of peeling.
- the gas generated by decomposition of the adhesive layer itself at high temperature and the gas generated from moisture in the adhesive layer are as described above. Not only does it cause poor adhesion, but it also prevents the vacuum environment from being maintained.
- the adhesive composition which has specific acrylic resin as a main component is proposed as an adhesive composition which has favorable heat resistance and exhibits sufficient adhesive strength in a high temperature environment (patent document 5).
- an adhesive resin composition having heat resistance intended to be used for bonding electronic components and substrates an alicyclic structure-containing polymer having a specific molecular weight and a low molecular weight compound having a specific molecular weight
- an adhesive composition containing the above Patent Document 6
- the main object of the present invention is to provide an adhesive composition suitable for forming an adhesive layer for temporarily fixing the substrate and a support such as a glass plate or film when a substrate such as a wafer is processed.
- the present invention has good heat resistance that does not cause deterioration of resin or adhesion failure due to generation of gas even when exposed to a high temperature during processing of a substrate, and PGMEA used in a photoresist or the like.
- An adhesive layer that exhibits sufficient resistance to various chemicals is formed, and after processing the substrate, the adhesive layer can be quickly peeled off, and an adhesive composition excellent in flexibility is provided. It is.
- the present inventors have intensively studied to solve the above problems.
- a resin obtained by polymerizing a monomer component containing a cycloolefin monomer (a1) as a resin having excellent heat resistance and being hardly soluble in various chemical solutions such as PGMEA used in a photoresist or the like ( A) was selected.
- this resin (A) alone has a slow peeling rate when the adhesive layer is peeled off, in order to compensate for this, PGMEA, etc., which is excellent in heat resistance like the resin (A) and used in a photoresist, etc.
- the present inventors have found that the above problems can be solved at once by using an adhesive composition in which these two types of resins are dissolved in an organic solvent (S) at a specific ratio, and the present invention has been completed.
- the adhesive composition of the present invention is selected from the group consisting of a resin (A) obtained by polymerizing a monomer component containing a cycloolefin monomer (a1), a terpene resin, a rosin resin, and a petroleum resin.
- the at least one resin (B) is dissolved in an organic solvent (S).
- the glass transition point of the resin (A) is 60 ° C. or higher
- the softening point of the resin (B) is 80 to 160 ° C.
- the molecular weight of the resin (B) is 300 to 3000.
- the substrate processing method includes a step of temporarily fixing a support to a substrate such as a wafer via an adhesive layer, a step of processing the substrate including a step of heating the substrate, and a support from the substrate. And the step of peeling the body with a solvent, wherein the adhesive layer is formed of the above-mentioned adhesive composition.
- the adhesive composition of the present invention it is possible to form an adhesive layer for temporarily fixing the substrate and a support such as a glass plate or film when a substrate such as a wafer is processed.
- This adhesive layer has good heat resistance so as not to cause deterioration of the resin or poor adhesion due to generation of gas even when exposed to a high temperature during processing of the substrate.
- the adhesive layer exhibits sufficient resistance to various chemicals such as PGMEA used in a photoresist and the like, can be peeled quickly after processing the substrate, and is excellent in flexibility. As a result, the semiconductor wafer can be prevented from being damaged, the circuit pattern on the wafer surface can be protected, and a through electrode can be formed on the wafer through processes including a high temperature process and a high vacuum process. It is done.
- the adhesive composition of the present invention is obtained by dissolving a specific resin (A) and a specific resin (B) in an organic solvent at a specific ratio.
- the resin (A) in the present invention is a resin obtained by polymerizing a monomer component containing the cycloolefin monomer (a1). Specifically, as the resin (A), a ring-opening (co) polymer of a monomer component containing a cycloolefin monomer (a1) and a monomer component containing a cycloolefin monomer (a1) are added ( Co) polymerized resin and the like.
- Examples of the cycloolefin monomer (a1) contained in the monomer component constituting the resin (A) include bicyclics such as norbornene and norbornadiene, tricyclics such as dicyclopentadiene and dihydroxypentadiene, tetra Tetracycles such as cyclododecene, pentacycles such as cyclopentadiene trimer, heptacycles such as tetracyclopentadiene, or polycyclic alkyl-substituted, alkenyl-substituted, alkylidene-substituted, aryl-substituted Etc.
- bicyclics such as norbornene and norbornadiene
- tricyclics such as dicyclopentadiene and dihydroxypentadiene
- tetra Tetracycles such as cyclododecene
- pentacycles such as cyclopentadiene trimer
- norbornene-based monomers selected from the group consisting of norbornene, tetracyclododecene, and alkyl-substituted products thereof, as shown by the following general formula (1), are preferable.
- the alkyl group in the alkyl-substituted product include alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl and hexyl groups.
- alkenyl group in the alkenyl substituent include alkenyl groups having 2 to 6 carbon atoms such as vinyl, allyl, butenyl, pentenyl, hexenyl, and cyclohexenyl groups.
- alkylidene group in the substituted alkylidene examples include alkylidene groups having 1 to 6 carbon atoms such as ethylidene, propylidene, butylidene, and hexylidene.
- alkylidene groups having 1 to 6 carbon atoms such as ethylidene, propylidene, butylidene, and hexylidene.
- aryl group in the aryl substituent include phenyl, tolyl, and naphthyl groups.
- R 1 and R 2 are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is 0 or 1.
- a monomer selected from the group consisting of norbornene or an alkyl-substituted product thereof (in the general formula (1), n is 0) is more preferable from the viewpoint of achieving both heat resistance and flexibility.
- the monomer component constituting the resin (A) may contain another monomer copolymerizable with the cycloolefin monomer (a1).
- the alkene monomer (a2) is also preferably contained.
- the alkene monomer (a2) include ⁇ -olefins such as ethylene, propylene, 1-butene, isobutene and 1-hexene.
- the alkene monomer (a2) may be linear or branched.
- R 3 to R 6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- the monomer component constituting the resin (A) is preferably 50% by mass or more of the cycloolefin monomer (a1), more preferably 60% by mass or more of the cycloolefin monomer (a1). It is good to be. When the cycloolefin monomer (a1) is less than 50% by mass of the entire monomer component, the adhesive strength in a high temperature environment tends to be insufficient.
- the resin (A) includes, for example, a monomer component composed of the cycloolefin monomer (a1) represented by the above formula (1) and the alkene monomer (a2) represented by the above formula (2).
- the polymerization method and polymerization conditions for polymerizing the monomer components are not particularly limited and may be appropriately set according to a conventional method.
- Examples of commercially available products that can be used as the resin (A) include “TOPAS” manufactured by Polyplastics, “APEL” manufactured by Mitsui Chemicals, “ZEONOR” and “ZEONEX” manufactured by Nippon Zeon, and JSR. “ARTON” manufactured by the company can be mentioned.
- the glass transition point (Tg) of the resin (A) is 60 ° C. or higher.
- the glass transition point of the resin (A) is 70 ° C. or higher.
- the adhesive composition softens when exposed to a high temperature environment, resulting in poor adhesion.
- the resin (B) in the present invention is at least one resin selected from the group consisting of terpene resins, rosin resins and petroleum resins.
- the terpene resin include a terpene resin, a terpene phenol resin, a modified terpene resin, a hydrogenated terpene resin, and a hydrogenated terpene phenol resin.
- the rosin resin include rosin. Rosin ester, hydrogenated rosin, hydrogenated rosin ester, polymerized rosin, polymerized rosin ester, modified rosin and the like.
- the petroleum resin include aliphatic or aromatic petroleum resins, hydrogenated petroleum resins, modified petroleum. Resin, alicyclic petroleum resin, coumarone-indene petroleum resin and the like. Among these, hydrogenated terpene resins and hydrogenated petroleum resins are preferable.
- the softening point of the resin (B) is 80 to 160 ° C.
- the softening point of the resin (B) is less than 80 ° C.
- the adhesive composition is softened when exposed to a high temperature environment, resulting in poor adhesion.
- the softening point of resin (B) exceeds 160 degreeC, the peeling rate at the time of peeling an adhesive composition will become slow.
- the molecular weight of the resin (B) is 300 to 3000.
- the molecular weight of the resin (B) is less than 300, the heat resistance becomes insufficient, and the amount of degassing increases in a high temperature environment.
- the molecular weight of the resin (B) exceeds 3000, the peeling speed when peeling the adhesive composition is slowed down.
- the molecular weight of resin (B) in this invention means the molecular weight of polystyrene conversion measured by gel permeation chromatography (GPC).
- the resin (A) is more than the above range (in other words, when the resin (B) is too much less than the range)
- the peeling rate when peeling the adhesive composition is slowed
- the resin (A) is less than the above range (in other words, if the resin (B) is too much above the range)
- the adhesive composition will be softened when exposed to a high temperature environment. Cause poor adhesion.
- the organic solvent (S) is not particularly limited as long as it can dissolve the resin (A) and the resin (B).
- a hydrocarbon solvent is preferable, and a terpene solvent is more preferable. It is done.
- only 1 type may be sufficient as an organic solvent (S), and 2 or more types may be sufficient as it.
- terpene solvent examples include ⁇ -pinene, camphene, pinane, myrcene, dihydromyrcene, p-menthane, 3-carene, p-menthadiene, ⁇ -terpinene, ⁇ -terpinene, ⁇ -ferrandrene, osymene, Limonene, p-cymene, ⁇ -terpinene, terpinolene, 1,4-cineole, 1,8-cineole, rose oxide, linalool oxide, fencon, ⁇ -cyclocitral, osmenol, tetrahydrolinalol, linalool, tetrahydromegol, isopulegol, Dihydrolinalool, isodihydrolabandulol, ⁇ -cyclocitral, citronellal, L-mentholone, linalyl formate, dihydroterpineol, ⁇ -terpineol
- the solid content concentration of the adhesive composition of the present invention (that is, the resin (A) and the resin (B) with respect to the total mass of the resin (A), the resin (B) and the organic solvent (S).
- the ratio of the total mass is usually 20 to 60% by mass.
- additives such as a plasticizer and an antioxidant can be added as necessary. It can also contain in the range which does not impair the effect of invention.
- the adhesive composition of the present invention has good heat resistance that does not cause adhesion failure due to deterioration of the resin or generation of gas even when exposed to high temperatures, and against various chemicals used in photoresists and the like.
- An adhesive layer exhibiting sufficient resistance can be formed, and when the adhesive layer is no longer needed, it can be quickly peeled off by a treatment such as immersion in a predetermined solvent.
- medical solutions used with a photoresist etc. typically, PGMEA is mentioned, However
- peeling solvent a “peeling solvent” used when peeling the adhesive bond layer formed with the adhesive composition of this invention
- the thing similar to the said organic solvent (S) is mentioned.
- the same solvent as the organic solvent (S) is used as the peeling solvent.
- Evaluation of the adhesive composition was performed by each test method described later using the adhesive composition to form a coating film on a silicon wafer and using the resulting coated silicon wafer as a test piece.
- coating the obtained adhesive composition on a 6-inch silicon wafer so that a dry film thickness might be set to 15 micrometers a test piece is 110 degreeC for 3 minutes, then 150 degreeC for 3 minutes, then 200 It was created by drying at 3 ° C. for 3 minutes.
- the test piece used for the evaluation of the flexibility of the coating film was applied in the above method so that the dry film thickness was 50 ⁇ m, and then dried at 150 ° C. for 3 minutes and then at 200 ° C. for 3 minutes. Changed and created.
- ⁇ Drug resistance> Various chemicals used in photoresists and the like are kept at 23 ° C., and a test piece (silicon wafer with a coating film) is immersed therein, and the state of the coating film is visually observed after 5 minutes. In the case where no crack and dissolved portion were observed, “ ⁇ ” was determined, and in the case where at least one of the crack and dissolved portion was observed in the coating film layer, “ ⁇ ” was determined.
- medical solution it evaluated using the following (abbreviation in a parenthesis).
- the test piece (silicon wafer with a coating film) was heated from 40 ° C. to 250 ° C., and the amount of gas generated (degassing amount) from the coating film was measured by the TDS method (Thermal Desorption Spectroscopy method: temperature-programmed desorption analysis method). Based on the above, the measurement was performed under the following conditions using a TDS measurement device (emission gas measurement device; “EMD-WA1000” manufactured by Electronic Science Co., Ltd.).
- the degassing amount measured at temperatures up to 100 ° C. is the amount of water vapor or azeotropic gas generated from the moisture absorbed by the adhesive composition, and is measured at temperatures exceeding 100 ° C.
- the degassing amount is the amount of gas generated when the adhesive composition itself is decomposed by heat. Therefore, the heat resistance of the adhesive composition can be comprehensively evaluated by looking at the strength at 100 ° C. (degas amount) and the strength at 200 ° C. (degas amount).
- a hydrogenated terpene resin (“Clearon P135” manufactured by Yasuhara Chemical Co., Ltd., softening point: 135 ° C., molecular weight: 820; this is referred to as “terpene resin (1)”) was used.
- These resin (A) and resin (B) were dissolved in a terpene solvent (p-menthane) in the proportions shown in Table 1 to obtain an adhesive composition having a solid content concentration of 30% by mass.
- Example 4 to 6 and Comparative Examples 5 to 8 As the resin (A), the cycloolefin copolymer (“TOPAS8007” manufactured by Polyplastics) used in Examples 1 to 3 and Comparative Examples 1 to 4 was used. As the resin (B), a hydrogenated terpene resin (“Clearon P115” manufactured by Yasuhara Chemical Co., Ltd., softening point: 115 ° C., molecular weight: 650; this is referred to as “terpene resin (2)”) was used. These resin (A) and resin (B) were dissolved in a terpene solvent (p-menthane) in the proportions shown in Table 2 to obtain an adhesive composition having a solid content concentration of 30% by mass.
- a terpene solvent p-menthane
- Example 7 to 9 and Comparative Examples 9 to 12 As the resin (A), the cycloolefin copolymer (“TOPAS8007” manufactured by Polyplastics) used in Examples 1 to 3 and Comparative Examples 1 to 4 was used. As the resin (B), a hydrogenated terpene resin (“Clearon P105” manufactured by Yasuhara Chemical Co., Ltd., softening point: 105 ° C., molecular weight: 630; this is referred to as “terpene resin (3)”) was used. These resin (A) and resin (B) were dissolved in a terpene solvent (p-menthane) in the proportions shown in Table 3 to obtain an adhesive composition having a solid content concentration of 30% by mass.
- a terpene solvent p-menthane
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Abstract
Description
このような製造工程においては、薄板化したウェハー自体が脆く破損しやすいため、これを補強する必要がある。加えて、例えば研削加工で生じた研磨屑などによってウェハー表面に形成した回路パターンが汚染されるのを防ぐ必要もある。そこで、ウェハーの破損を防止し、ウェハー表面の回路パターンを保護する方法として、以下の方法が知られている。
(1)ウェハーに支持体を接着剤層で仮止めした状態で研削加工し、その後、支持体を剥離する手法(特許文献1、2)
(2)ウェハー表面の回路パターン面に接着剤層を備えた粘着フィルムを貼り付けた状態で研削加工し、その後、粘着フィルムを剥離する手法(特許文献3、4)
また、特許文献6記載の接着剤組成物には、脂環式構造含有重合体が有する極性基に起因して接着剤層が吸湿しやすく、その結果、高温下で発生するガス量が増えるため接着不良を招いたり、接着剤層を剥離する際の剥離速度が遅いため、生産性の点で不利になったりするという問題があった。
また、本発明に係る基板の加工方法は、ウェハー等の基板に接着剤層を介して支持体を仮止めする工程と、前記基板の加熱工程を含む前記基板の加工工程と、前記基板から支持体を溶剤で剥離する工程とを含み、前記接着剤層が、上記の接着剤組成物によって形成されたものであることを特徴とする。
本発明における樹脂(A)は、シクロオレフィン系モノマー(a1)を含む単量体成分を重合してなる樹脂である。具体的には、樹脂(A)としては、シクロオレフィン系モノマー(a1)を含む単量体成分の開環(共)重合体、シクロオレフィン系モノマー(a1)を含む単量体成分を付加(共)重合させた樹脂などが挙げられる。
前記アルキル置換体におけるアルキル基としては、例えばメチル、エチル、プロピル、ブチル、ペンチル、ヘキシル基などの炭素数1~6のアルキル基が挙げられる。アルケニル置換体におけるアルケニル基としては、例えばビニル、アリル、ブテニル、ペンテニル、ヘキセニル、シクロヘキセニル基等の炭素数2~6のアルケニル基が挙げられる。アルキリデン置換体におけるアルキリデン基としては、例えばエチリデン、プロピリデン、ブチリデン、ヘキシリデンなどの炭素数1~6のアルキリデン基が挙げられる。アリール置換体におけるアリール基としては、例えばフェニル、トリル、ナフチル基などが挙げられる。
中でも、ノルボルネンまたはそのアルキル置換体からなる群より選ばれるモノマー(前記一般式(1)中、nが0)が、耐熱性と柔軟性を両立させる観点から、より好ましい。
なお、前記樹脂(A)は、例えば、上述した式(1)で示されるシクロオレフィン系モノマー(a1)と上述した式(2)で示されるアルケンモノマー(a2)とからなる単量体成分を重合させてなる樹脂のように、極性基を有していない二元共重合体であることが、高温下でのガスの発生を抑制するうえで好ましい。
前記単量体成分を重合する際の重合方法や重合条件等については、特に制限はなく、常法に従い適宜設定すればよい。
前記テルペン系溶剤としては、例えば、α-ピネン、カンフェン、ピナン、ミルセン、ジヒドロミルセン、p-メンタン、3-カレン、p-メンタジエン、α-テルピネン、β-テルピネン、α-フェランドレン、オシメン、リモネン、p-サイメン、γ-テルピネン、テルピノーレン、1,4-シネオール、1,8-シネオール、ローズオキサイド、リナロールオキサイド、フェンコン、α-シクロシトラール、オシメノール、テトラヒドロリナロール、リナロール、テトラヒドロムゴール、イソプレゴール、ジヒドロリナロール、イソジヒドロラバンジュロール、β-シクロシトラール、シトロネラール、L-メントン、ギ酸リナリル、ジヒドロテルピネオール、β-テルピネオール、メントール、ミルセノール、L-メントール、ピノカルベオール、α-テルピネオール、γ-テルピネオール、ノポール、ミルテノール、ジヒドロカルベオール、シトロネロール、ミルテナール、ジヒドロカルボン、d-プレゴン、ゲラニルエチルエーテル、ギ酸ゲラニル、ギ酸ネリル、ギ酸テルピニル、酢酸イソジヒドロラバンジュリル、酢酸テルピニル、酢酸リナリル、酢酸ミルセニル、酢酸ボルニル、プロピオン酸メンチル、プロピオン酸リナリル、ネロール、カルベオール、ペリラアルコール、ゲラニオール、サフラナール、シトラール、ペリラアルデヒド、シトロネリルオキシアセトアルデヒド、ヒドロキシシトロネラール、ベルベノン、d-カルボン、L-カルボン、ピペリトン、ピペリテノン、ギ酸シトロネリル、酢酸イソボルニル、酢酸メンチル、酢酸シトロネリル、酢酸カルビル、酢酸ジメチルオクタニル、酢酸ネリル、酢酸イソプレゴール、酢酸ジヒドロカルビル、酢酸ノピル、酢酸ゲラニル、プロピオン酸ボルニル、プロピオン酸ネリル、プロピオン酸カルビル、プロピオン酸テルピニル、プロピオン酸シトロネリル、プロピオン酸イソボルニル、イソ酪酸リナリル、イソ酪酸ネリル、酪酸リナリル、酪酸ネリル、イソ酪酸テルピニル、酪酸テルピニル、イソ酪酸ゲラニル、酪酸シトロネリル、ヘキサン酸シトロネリル、イソ吉草酸メンチル、β-カリオフィレン、セドレン、ビサボレン、ヒドロキシシトロネロール、ファルネソール、イソ酪酸ロジニル等が挙げられる。これらの中でも、リモネンおよびp-メンタンの少なくとも一方をテルペン系溶剤とすることが、溶解性の観点から好ましく、特に好ましくはp-メンタンがよい。
なお、試験片は、得られた接着剤組成物を6インチのシリコンウェハー上に、乾燥膜厚が15μmとなるように塗布した後、110℃で3分間、次いで150℃で3分間、次いで200℃で3分間の条件で乾燥することにより作成した。ただし、塗膜の柔軟性の評価に供する試験片は、上記方法において、乾燥膜厚が50μmとなるように塗布した後、150℃で3分間、次いで200℃で3分間の条件で乾燥するよう変更して、作成した。
試験片(塗膜付きシリコンウェハー)を23℃に保持したp-メンタン中に浸漬させ、5分後に目視にて塗膜の状態を観察して、塗膜層が完全に溶解している場合を「○」、塗膜層が溶け残っている場合を「×」と判定した。また、試験片は塗膜が完全に溶解するまでp-メンタン中に浸漬させるようにし、塗膜が完全に溶解するまでの時間を測定し、この溶解時間(T(sec))と、予め測定しておいた試験片上の塗膜の厚さ(L(nm))とから溶解速度(L/T(nm/sec))を算出した。溶解速度は60nm/sec以上であることが生産性の点で望ましい。
フォトレジスト等で使用される各種薬液を23℃に保持し、その中に試験片(塗膜付きシリコンウェハー)を浸漬させ、5分後に目視にて塗膜の状態を観察して、塗膜層にクラックおよび溶解部分が認められない場合を「○」、塗膜層にクラックおよび溶解部分の少なくとも一方が認められる場合を「×」と判定した。なお、薬液としては下記のもの(括弧内は略号)を用いて評価した。
・プロピレングリコールモノメチルエーテルアセテート(PGMEA)
・水
・イソプロピルアルコール(IPA)
・プロピレングリコールモノメチルエーテル(PGME)
・N-メチルピロリドン(NMP)
・ジメチルスルホキシド(DMSO)
・2.38質量%テトラメチルアンモニウムハイドロオキサイド水溶液(TMAH)
・5質量%水酸化ナトリウム水溶液(NaOH)
・1質量%フッ化水素水溶液(1-HF)
・3質量%フッ化水素水溶液(3-HF)
上述したように、乾燥膜厚と乾燥条件を変更して得た試験片(膜厚50μmの塗膜を備えたシリコンウェハー)を目視にて観察して、塗膜層にクラックが認められない場合を「○」、塗膜層にクラックが認められる場合を「×」と判定した。
試験片(塗膜付きシリコンウェハー)を40℃から250℃まで昇温し、塗膜からのガスの発生量(脱ガス量)を、TDS法(Thermal Desorption Spectroscopy法:昇温脱離分析法)に基づき、TDS測定装置(放出ガス測定装置;電子科学(株)製「EMD-WA1000」)を用いて以下の条件で測定した。
〔TDS測定装置の条件〕
Width:100
Center Mass Number:50
Gain:9
Scan Speed:4
Emult Volt:1.3kV
そして、100℃、200℃においてTDS測定装置から求められる強度(Intensity)が共に10000未満である場合を「○」、少なくとも一方が10000以上である場合を「×」と判定した。
通常、100℃までの温度で測定される脱ガス量は、接着剤組成物が吸湿した水分に由来して生じた水蒸気またはその共沸ガスの発生量であり、100℃を超える温度で測定される脱ガス量は、接着剤組成物自体が熱により分解されて生じたガスの発生量である。よって、100℃における強度(脱ガス量)と、200℃における強度(脱ガス量)を見ることにより、接着剤組成物の耐熱性を総合的に評価することができる。
試験片(塗膜付きシリコンウェハー)を230℃で1時間加熱した後に、23℃に保持したp-メンタン中に浸漬させ、5分後に目視にて塗膜の状態を観察して、塗膜層が完全に溶解している場合を「○」、塗膜層が溶け残っている場合を「×」と判定した。
樹脂(A)として、ノルボルネンとエチレンをメタロセン触媒にて共重合したシクロオレフィンコポリマー(ポリプラスチック社製「TOPAS8007」、ノルボルネン:エチレン=65:35(質量比)、ガラス転移点:70℃、Mw:98200、Mw/Mn:1.69)を用いた。樹脂(B)として、水添テルペン樹脂(ヤスハラケミカル社製「クリアロンP135」、軟化点:135℃、分子量:820;これを「テルペン樹脂(1)」とする)を用いた。これらの樹脂(A)と樹脂(B)とを表1に示す割合でテルペン系溶剤(p-メンタン)に溶解させて、固形分濃度30質量%の接着剤組成物を得た。
樹脂(A)として、実施例1~3および比較例1~4で用いたシクロオレフィンコポリマー(ポリプラスチック社製「TOPAS8007」)を用いた。樹脂(B)として、水添テルペン樹脂(ヤスハラケミカル社製「クリアロンP115」、軟化点:115℃、分子量:650;これを「テルペン樹脂(2)」とする)を用いた。これらの樹脂(A)と樹脂(B)とを表2に示す割合でテルペン系溶剤(p-メンタン)に溶解させて、固形分濃度30質量%の接着剤組成物を得た。
樹脂(A)として、実施例1~3および比較例1~4で用いたシクロオレフィンコポリマー(ポリプラスチック社製「TOPAS8007」)を用いた。樹脂(B)として、水添テルペン樹脂(ヤスハラケミカル社製「クリアロンP105」、軟化点:105℃、分子量:630;これを「テルペン樹脂(3)」とする)を用いた。これらの樹脂(A)と樹脂(B)とを表3に示す割合でテルペン系溶剤(p-メンタン)に溶解させて、固形分濃度30質量%の接着剤組成物を得た。
Claims (8)
- シクロオレフィン系モノマー(a1)を含む単量体成分を重合してなる樹脂(A)と、テルペン系樹脂、ロジン系樹脂および石油樹脂からなる群より選ばれる少なくとも1種の樹脂(B)と、これらの樹脂(A)および(B)を溶解する有機溶剤(S)とを含む接着剤組成物であって、
前記樹脂(A)はガラス転移点が60℃以上であり、
前記樹脂(B)は軟化点が80~160℃であり、かつ分子量が300~3000であるとともに、
前記樹脂(A)と前記樹脂(B)との配合割合が(A):(B)=80:20~55:45(質量比)であることを特徴とする接着剤組成物。 - 前記樹脂(A)を構成する前記単量体成分は、50質量%以上がシクロオレフィン系モノマー(a1)である、請求項1記載の接着剤組成物。
- 前記樹脂(A)を構成する前記単量体成分は、アルケンモノマー(a2)をも含有する、請求項1または2記載の接着剤組成物。
- 前記シクロオレフィン系モノマー(a1)がノルボルネン系モノマーである、請求項1~3のいずれかに記載の接着剤組成物。
- 前記有機溶剤(S)がテルペン系溶剤である、請求項1~4のいずれかに記載の接着剤組成物。
- 基板に接着剤層を介して支持体を仮止めする工程と、
前記基板の加熱工程を含む前記基板の加工工程と、
前記基板から支持体を溶剤で剥離する工程と
を含み、
前記接着剤層が、請求項1~5のいずれかに記載の接着剤組成物によって形成されたものである、基板の加工方法。 - 前記基板がウェハーである、請求項6記載の加工方法。
- 前記基板から支持体を剥離させる溶剤が、前記接着剤組成物に用いた溶剤(S)と同じ溶剤である、請求項6または7記載の加工方法。
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JP2011518384A JP5308524B2 (ja) | 2009-06-11 | 2010-05-20 | 接着剤組成物 |
KR1020127000105A KR101345086B1 (ko) | 2009-06-11 | 2010-05-20 | 접착제 조성물 |
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JP (1) | JP5308524B2 (ja) |
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JP2012001605A (ja) * | 2010-06-15 | 2012-01-05 | Tokyo Ohka Kogyo Co Ltd | 接着剤組成物 |
JP2012166489A (ja) * | 2011-02-16 | 2012-09-06 | Tokyo Ohka Kogyo Co Ltd | 積層体 |
KR20120131103A (ko) | 2011-05-24 | 2012-12-04 | 도오꾜오까고오교 가부시끼가이샤 | 박리용 조성물 및 박리 방법 |
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KR20140059793A (ko) * | 2011-09-16 | 2014-05-16 | 린텍 가부시키가이샤 | 다이싱 시트용 기재 필름 및 다이싱 시트 |
JP2015078313A (ja) * | 2013-10-17 | 2015-04-23 | 東京応化工業株式会社 | 剥離用組成物及び剥離方法 |
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JP2012166489A (ja) * | 2011-02-16 | 2012-09-06 | Tokyo Ohka Kogyo Co Ltd | 積層体 |
JP2013007026A (ja) * | 2011-05-24 | 2013-01-10 | Tokyo Ohka Kogyo Co Ltd | 剥離用組成物および剥離方法 |
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US20120073741A1 (en) | 2012-03-29 |
KR20120024929A (ko) | 2012-03-14 |
TW201114868A (en) | 2011-05-01 |
JP5308524B2 (ja) | 2013-10-09 |
KR101345086B1 (ko) | 2013-12-26 |
TWI454545B (zh) | 2014-10-01 |
JPWO2010143510A1 (ja) | 2012-11-22 |
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