JP5157255B2 - 感光性接着剤組成物、及びそれを用いた接着フィルム、接着シート、接着剤パターン、並びに半導体装置 - Google Patents
感光性接着剤組成物、及びそれを用いた接着フィルム、接着シート、接着剤パターン、並びに半導体装置 Download PDFInfo
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- JP5157255B2 JP5157255B2 JP2007139504A JP2007139504A JP5157255B2 JP 5157255 B2 JP5157255 B2 JP 5157255B2 JP 2007139504 A JP2007139504 A JP 2007139504A JP 2007139504 A JP2007139504 A JP 2007139504A JP 5157255 B2 JP5157255 B2 JP 5157255B2
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- Prior art keywords
- diamine
- adhesive composition
- adhesive
- photosensitive adhesive
- polyimide
- Prior art date
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 45
- 230000007261 regionalization Effects 0.000 claims abstract description 31
- 238000011161 development Methods 0.000 claims abstract description 22
- 230000018109 developmental process Effects 0.000 claims abstract description 22
- 238000003860 storage Methods 0.000 claims abstract description 19
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- 150000004985 diamines Chemical class 0.000 claims description 60
- -1 aliphatic ether diamine Chemical class 0.000 claims description 57
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 56
- 239000000758 substrate Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 32
- 239000010703 silicon Substances 0.000 claims description 31
- 229910052710 silicon Inorganic materials 0.000 claims description 31
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 29
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- 239000003822 epoxy resin Substances 0.000 claims description 25
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- 239000000463 material Substances 0.000 claims description 20
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
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- 125000000217 alkyl group Chemical group 0.000 claims description 5
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- PLGBRGZNHLWMKD-UHFFFAOYSA-N bis[2-aminoethyl(dimethyl)silyl] dimethyl silicate Chemical compound NCC[Si](C)(C)O[Si](OC)(OC)O[Si](C)(C)CCN PLGBRGZNHLWMKD-UHFFFAOYSA-N 0.000 description 1
- AOMMCEXPXYKABF-UHFFFAOYSA-N bis[4-aminobutyl(dimethyl)silyl] dimethyl silicate Chemical compound NCCCC[Si](C)(C)O[Si](OC)(OC)O[Si](C)(C)CCCCN AOMMCEXPXYKABF-UHFFFAOYSA-N 0.000 description 1
- QCKVTJUJXXGBDQ-UHFFFAOYSA-N bis[4-aminobutyl(diphenyl)silyl] dimethyl silicate Chemical compound C=1C=CC=CC=1[Si](CCCCN)(C=1C=CC=CC=1)O[Si](OC)(OC)O[Si](CCCCN)(C=1C=CC=CC=1)C1=CC=CC=C1 QCKVTJUJXXGBDQ-UHFFFAOYSA-N 0.000 description 1
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- OOJITEPTYTVULX-UHFFFAOYSA-N bis[5-aminopentyl(diphenyl)silyl] dimethyl silicate Chemical compound C=1C=CC=CC=1[Si](CCCCCN)(C=1C=CC=CC=1)O[Si](OC)(OC)O[Si](CCCCCN)(C=1C=CC=CC=1)C1=CC=CC=C1 OOJITEPTYTVULX-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
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- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
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- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- MLMVPBFKPWONNM-UHFFFAOYSA-N prop-2-enoic acid;urea Chemical compound NC(N)=O.OC(=O)C=C MLMVPBFKPWONNM-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- RTHVZRHBNXZKKB-UHFFFAOYSA-N pyrazine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(C(O)=O)N=C1C(O)=O RTHVZRHBNXZKKB-UHFFFAOYSA-N 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
- H01L2224/29001—Core members of the layer connector
- H01L2224/2901—Shape
- H01L2224/29012—Shape in top view
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01019—Potassium [K]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/102—Material of the semiconductor or solid state bodies
- H01L2924/1025—Semiconducting materials
- H01L2924/10251—Elemental semiconductors, i.e. Group IV
- H01L2924/10253—Silicon [Si]
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Die Bonding (AREA)
Description
また、本発明は、(13)前記ジアミンが、下記一般式(IV)で表されるシロキサンジアミンをジアミン全体に対して1〜20モル%含む、前記(11)又は(12)に記載の感光性接着剤組成物に関する。
また、本発明は、(14)さらに、熱硬化性樹脂、放射線重合性化合物、及び光重合開始剤を含有する前記(6)〜(13)のいずれか一項に記載の感光性接着剤組成物に関する。
さらに、良好な接着性を付与できる点で、上記ジアミンは、下記一般式(IV)で表されるシロキサンジアミンをジアミン全体に対して1〜20モル%含むことが好ましい。
本発明の感光性接着剤組成物は、さらに、熱硬化性樹脂、放射線重合性化合物、及び光重合開始剤を含有することが好ましい。
熱硬化性樹脂を用いる場合、これを硬化させるために、硬化剤、硬化促進剤、触媒等の添加剤を感光性接着剤組成物中に適宜加えることができる。触媒を添加する場合は助触媒を必要に応じて使用することができる。
実施例に限定されるものではない。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内に3,5−ジアミノ安息香酸(以下「DABA」と略す)7.6g及びNMPを仕込んだ。次いで4,4’−オキシジフタル酸二無水物(以下「ODPA」と略す)15.5gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。滴下終了後、更に室温で5時間攪拌した。次に該フラスコに水分受容器付の還流冷却器を取り付け、キシレンを加え、180℃に昇温させてその温度を5時間保持した。こうして得られた溶液を室温まで冷却した後、蒸留水中に投じて再沈殿させた。得られた沈殿物を真空乾燥機で乾燥しポリイミド(以下「ポリイミドPI−1」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内にDABA6.84g、脂肪族エーテルジアミン(BASF社製「D2000」(商品名)、分子量1998)9.99g及びNMPを仕込んだ。次いでODPA16gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−2」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内にDABA2.28g、脂肪族エーテルジアミン(BASF社製「D400」(商品名)、分子量433)15.16g及びNMPを仕込んだ。次いでODPA16gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てポリイミドPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−3」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内にDABA1.9g、脂肪族エーテルジアミン(BASF社製「D400」(商品名)、分子量433)15.16g及び1,1,3,3−テトラメチル−1,3−ビス(4−アミノフェニル)ジシロキサン(信越化学製「LP−7100」(商品名)分子量348.4)0.87g及びNMPを仕込んだ。次いでODPA16gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てポリイミドPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−4」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内にm−フェニレンジアミン5.4g及びNMPを仕込んだ。次いでODPA15.5gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てポリイミドPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−5」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内に5,5‘−メチレン−ビス(アントラニリックアシッド)(以下「MBAA」と略す、分子量286.28)2.15g及び、脂肪族エーテルジアミン(BASF社製「D400」(商品名)、分子量433)15.59g及び1,1,3,3−テトラメチル−1,3−ビス(4−アミノフェニル)ジシロキサン(信越化学製「LP−7100」(商品名)分子量348.4)2.26g及びNMPを仕込んだ。次いでODPA17gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てポリイミドPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−6」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内に1,12−ジアミノドデカン2.10g(以下「DDO」と略す)、脂肪族エーテルジアミン(BASF社製「D2000」(商品名)、分子量1998)17.98g及び1,1,3,3−テトラメチル−1,3−ビス(4−アミノフェニル)ジシロキサン(信越化学製「LP−7100」(商品名)分子量348.4)2.61g及びNMPを仕込んだ。次いで4,4‘−(4,4’−イソプロピリデンジフェノキシ)ビス(フタル酸二無水物)(以下「BPADA」と略す)15.62gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てポリイミドPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−7」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内に2,2−ビス(4−アミノフェノキシフェニル)プロパン(以下「BAPP」と略す)6.83g、4,9−ジオキサデカン−1,12−ジアミン(以下「B−12」と略す)3.40g及びNMPを仕込んだ。次いでデカメチレンビストリメリテートニ無水物(以下「DBTA」と略す)17.40gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てポリイミドPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−8」という。)を得た。
攪拌機、温度計、及び窒素置換装置を備えたフラスコ内に5,5‘−メチレン−ビス(アントラニリックアシッド)(以下「MBAA」と略す、分子量286.28)14.3g及びNMPを仕込んだ。次いでODPA16gをNMPに溶解した溶液を反応系の温度が50℃を超えないように調整しながら上記フラスコ内に滴下した。これ以降の操作は全てポリイミドPI−1の合成と同様に行って、ポリイミド(以下「ポリイミドPI−9」という。)を得た。
ポリイミドPI−2、放射線重合性化合物としてのエトキシ化ビスフェノールAジメタクリレート(「BPE−100」(商品名)、新中村化学社製)、光重合開始剤としてのビス(2,4,6−トリメチルベンゾイル)−フェニルフォスフィンオキサイド(「I−819」(商品名)、チバ・スペシャルティ・ケミカルズ社製)、熱硬化性樹脂としてのビスフェノールF型エポキシ樹脂(「YDF−8170」(商品名)、東都化成社製)、及び前記エポキシ樹脂の硬化剤としてのα,α,α’−トリス(4−ヒドロキシフェニル)−1−エチル−4−イソプロピルベンゼン(「TrisP−PA」(商品名)、本州化学社製)を、表3に示す組成(重量部)となるように、シクロヘキサノン中で均一に混合して、接着フィルム形成用のワニスを調製した。このワニスを、離型用シリコーンで表面処理したPETフィルム上に塗布し、オーブン中にて90℃30分乾燥して、厚さ40μmの接着フィルムを形成させた。
それぞれ、表3、4に示す原料及び組成とした。実施例2〜6、及び比較例1〜6については、実施例1と同様にして、接着フィルムを作製した。なお、表3、4に示す原料の内容は下記のものを意味する。
U−2PPA:新中村化学、ウレタンアクリレート
YDF−8170:東都化成、ビスフェノールF型エポキシ樹脂
ESCN−195:住友化学、クレゾールノボラック型固体状エポキシ樹脂
TrisP−PA:本州化学、トリスフェノール化合物(α,α,α’−トリス(4−ヒドロキシフェニル)−1−エチル−4−イソプロピルベンゼン)
H−1:明和化成、フェノールノボラック
R972:日本アエロジル、疎水性フュームドシリカ(平均粒径:約16nm)
接着フィルムを、シリコンウェハ(6インチ径、厚さ400μm)上にロールで加圧することにより積層し、その上にマスクを載せた。そして、高精度平行露光機(オーク製作所製)で露光した後、テトラメチルアンモニウムハイドライド(TMAH)2.38%溶液を用いて1.5kgf/cm2の圧力でスプレー現像した。現像後、パターン形成(ライン幅1mm)されているか確認し、パターン形成されていた場合をA、パターン形成されていなかった場合をCとした。
支持台上に載せたシリコンウェハ(6インチ径、厚さ400μm)の裏面(支持台と反対側の面)に、接着フィルムをロール(温度100℃、線圧4kgf/cm、送り速度0.5m/分)で加圧することにより積層した。PETフィルムを剥がし、接着フィルム上に、厚み80μm、幅10mm、長さ40mmのポリイミドフィルム「ユーピレックス」(商品名)を前記と同様の条件でロールにより加圧して積層した。このようにして準備したサンプルについて、レオメータ「ストログラフE−S」(商品名)を用いて、室温で90°ピール試験を行って、接着フィルム−ユーピレックス間のピール強度を測定した。ピール強度が2N/cm以上のサンプルをA、2N/cm未満のサンプルをCとした。
厚みを約40μmに調整したフィルム状感光性接着剤組成物を35mm×10mmサイズに切断した試験片について、レオメトリックス製粘弾性アナライザーRSA−2を用いて、昇温速度:5℃/分、周波数:1Hz、測定温度:−50℃〜300℃の条件で測定し、tanδが極大値を示した温度をフィルムのTgとした。なお、tanδが複数の温度で極大値を示した場合には、それらのうち最も大きい極大値を示した温度をTgとした。
シリコンウェハ(6inch径、厚さ400μm)に、ロールと支持体とを有する装置を用いて、100℃、線圧:4kgf/cm、送り速度:0.5m/minの条件で接着フィルムをラミネートした。次に、高精度平行露光機(オーク製作所製)を用いて、PETフィルム側から露光量:1000mJ/cm2の条件で紫外線を照射した。PETフィルムをはく離し、接着フィルム上に感圧型のダイシングテープをラミネートした。その後、ダイサーを用いてシリコンウェハを接着フィルムとともに3mm×3mmサイズに裁断して、接着フィルムが積層されたシリコンチップを得た。このシリコンチップを10mm×10mm×0.55mm厚のガラス基板上に接着フィルムが挟まれる向きで載せ、120℃の熱盤上で500gf、10秒の条件で熱圧着した。その後、160℃のオーブン中で3時間加熱し、接着フィルムを加熱硬化させた。得られたサンプルについて、Dage製接着力試験機Dage−4000を用いて、25℃、又は260℃の熱盤上で、測定速度:50μm/秒、測定高さ:50μmの条件でシリコンチップ側にせん断方向の外力を加えたときの最大応力を25℃、又は260℃におけるせん断接着力とした。
接着フィルムを35mm×10mmの大きさに切断し、高精度平行露光機(オーク製作所)を用いて露光量:1000mJ/cm2の条件でPETフィルム側から紫外線を照射した。PETフィルムをはく離した露光後の接着フィルムを試験片として、レオメトリックス社製粘弾性アナライザー「RSA−2」を用いて、昇温速度:5℃/min、周波数:1Hz、測定温度:−50℃〜300℃の条件で測定した。この動的粘弾性測定から100℃における貯蔵弾性率を求めた。
接着フィルムを35mm×10mmの大きさに切断し、高精度平行露光機(オーク製作所)を用いて露光量:1000mJ/cm2の条件でPETフィルム側から紫外線を照射した。PETフィルムをはく離してから、接着フィルムを160℃のオーブン中で3時間の加熱により硬化させた。硬化された接着フィルムを試験片として、レオメトリックス社製粘弾性アナライザー「RSA−2」を用いて、昇温速度:5℃/min、周波数:1Hz、測定温度:−50℃〜300℃の条件で測定した。この動的粘弾性測定から260℃における貯蔵弾性率を求めた。
接着フィルムに対して、高精度平行露光機(オーク製作所)を用いて露光量:1000mJ/cm2の条件でPETフィルム側から紫外線を照射した。PETフィルムをはく離してから、接着フィルムを160℃のオーブン中で3時間の加熱により硬化させた。硬化された接着フィルムを乳鉢で細かく砕いて得た粉末を試料として、エスアイアイナノテクノロジー株式会社製示差熱熱重量同時測定装置EXSTAR 6300を用いて、昇温速度:10℃/分、空気流量:80mL/分、測定温度:40℃〜400℃の条件で熱重量分析を行った。この熱重量分析から、重量減少率が5%となる温度(5%重量減少温度)を求めた。
シリコンウェハ(6inch径、厚さ280μm)に、ロールと支持体とを有する装置を用いて、100℃、線圧:4kgf/cm、送り速度:0.5m/minの条件で接着フィルムをラミネートした。次に、高精度平行露光機(オーク製作所製)を用いて、PETフィルム側から露光量:1000mJ/cm2の条件で紫外線を照射した。PETフィルムをはく離し、接着フィルム上に感圧型のダイシングテープをラミネートした。その後、ダイサーを用いてシリコンウェハを接着フィルムとともに6.5mm×6.5mmサイズに裁断して、接着フィルムが積層されたシリコンチップを得た。このシリコンチップを、表面に厚さ15μmのソルダーレジスト層が付いた有機基板(厚さ0.1mm)上に接着フィルムが挟まれる向きで載せ、120℃の熱盤上で500gf、10秒の条件で熱圧着した。その後、トランスファモールドを行い(金型温度:180℃、キュアタイム:2min)、封止材をオーブン中で170℃5時間の条件で加熱硬化して半導体装置を得た(CSP96pin、封止領域:10mm×10mm、厚み:0.8mm)。この半導体装置を恒温恒湿器中で30℃60%RH192h吸湿処理した後、TAMURA製IRリフロー装置(半導体装置表面ピーク温度:260℃、温度プロファイル:半導体装置表面温度を基準にし、JEDEC規格に沿って調整)に3回繰り返し投入し、日立製作所製超音波探査映像装置HYE−FOUCUSを用いて、接着剤層の剥離、及び破壊の有無を調べた。その後、半導体装置の中心部を切断し、切断面を研磨した後、オリンパス製金属顕微鏡を用いて、半導体装置の断面を観察し、接着剤層の剥離、及び破壊の有無を調べた。これらの剥離、及び破壊が認められないことを耐リフロー性の評価基準とした(○:剥離、破壊無し、×:全て破壊または剥離)。
1a 接着剤パターン
3 基材
4 接着シート
5 基板
Claims (11)
- 現像によるパターン形成が可能な感光性接着剤組成物であって、パターン形成後の100℃における貯蔵弾性率が10MPa以下であり、
ポリイミド樹脂、
放射線重合性化合物、
エポキシ樹脂、
光重合開始剤、及び
エポキシ樹脂の硬化剤を含み、
前記ポリイミド樹脂はテトラカルボン酸二無水物とジアミンとを反応させて得られ、酸価が80〜180mg/KOHであり、
前記ジアミンは、下記一般式(III)で表される脂肪族エーテルジアミンをジアミン全体に対して10〜90モル%含むことを特徴とする感光性接着剤組成物。
(式中、Q 1 、Q 2 及びQ 3 は各々独立に炭素数1〜10のアルキレンを示し、n 1 は1〜80の整数を示す。) - 現像によるパターン形成が可能な感光性接着剤組成物であって、パターン形成後に、加熱硬化された後、260℃における貯蔵弾性率が1MPa以上であり、
ポリイミド樹脂、
放射線重合性化合物、
エポキシ樹脂、
光重合開始剤、及び
エポキシ樹脂の硬化剤を含み、
前記ポリイミド樹脂はテトラカルボン酸二無水物とジアミンとを反応させて得られ、酸価が80〜180mg/KOHであり、
前記ジアミンは、下記一般式(III)で表される脂肪族エーテルジアミンをジアミン全体に対して10〜90モル%含むことを特徴とする感光性接着剤組成物。
(式中、Q 1 、Q 2 及びQ 3 は各々独立に炭素数1〜10のアルキレンを示し、n 1 は1〜80の整数を示す。) - 現像によるパターン形成が可能な感光性接着剤組成物であって、パターン形成後に、加熱硬化された後、熱重量分析における重量減少率が5%となる温度が200℃以上であり、
ポリイミド樹脂、
放射線重合性化合物、
エポキシ樹脂、
光重合開始剤、及び
エポキシ樹脂の硬化剤を含み、
前記ポリイミド樹脂はテトラカルボン酸二無水物とジアミンとを反応させて得られ、酸価が80〜180mg/KOHであり、
前記ジアミンは、下記一般式(III)で表される脂肪族エーテルジアミンをジアミン全体に対して10〜90モル%含むことを特徴とする感光性接着剤組成物。
(式中、Q 1 、Q 2 及びQ 3 は各々独立に炭素数1〜10のアルキレンを示し、n 1 は1〜80の整数を示す。) - 現像によるパターン形成が可能な感光性接着剤組成物であって、前記接着剤組成物を介してシリコンチップをガラス基板に接着したときの25℃におけるせん断接着力が5MPa以上であり、
ポリイミド樹脂、
放射線重合性化合物、
エポキシ樹脂、
光重合開始剤、及び
エポキシ樹脂の硬化剤を含み、
前記ポリイミド樹脂はテトラカルボン酸二無水物とジアミンとを反応させて得られ、酸価が80〜180mg/KOHであり、
前記ジアミンは、下記一般式(III)で表される脂肪族エーテルジアミンをジアミン全体に対して10〜90モル%含むことを特徴とする感光性接着剤組成物。
(式中、Q 1 、Q 2 及びQ 3 は各々独立に炭素数1〜10のアルキレンを示し、n 1 は1〜80の整数を示す。) - 現像によるパターン形成が可能な感光性接着剤組成物であって、前記接着剤組成物を介してシリコンチップをガラス基板に接着したときの260℃におけるせん断接着力が0.5MPa以上であり、
ポリイミド樹脂、
放射線重合性化合物、
エポキシ樹脂、
光重合開始剤、及び
エポキシ樹脂の硬化剤を含み、
前記ポリイミド樹脂はテトラカルボン酸二無水物とジアミンとを反応させて得られ、酸価が80〜180mg/KOHであり、
前記ジアミンは、下記一般式(III)で表される脂肪族エーテルジアミンをジアミン全体に対して10〜90モル%含むことを特徴とする感光性接着剤組成物。
(式中、Q 1 、Q 2 及びQ 3 は各々独立に炭素数1〜10のアルキレンを示し、n 1 は1〜80の整数を示す。) - 請求項1〜7のいずれか一項に記載の感光性接着剤組成物からなる接着フィルム。
- 基材と、これの一方面上に設けられた請求項8記載の接着フィルムと、を備える接着シート。
- 請求項1〜7のいずれか一項に記載の感光性接着剤組成物からなる接着剤層を被着体上に形成し、該接着剤層をフォトマスクを介して露光し、露光後の接着剤層をアルカリ水溶液により現像処理することにより形成される、接着剤パターン。
- 請求項1〜7のいずれか一項に記載の感光性接着剤組成物を用いて被着体に接着された半導体チップを有する半導体装置。
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JP5458538B2 (ja) * | 2007-12-12 | 2014-04-02 | 日立化成株式会社 | 半導体装置及びその製造方法 |
JP5224121B2 (ja) * | 2008-04-25 | 2013-07-03 | 日立化成株式会社 | 感光性接着剤組成物、これを用いた感光性エレメント、レジストパターンの形成方法及び被接着部材の接着方法 |
CN103257527B (zh) * | 2008-08-27 | 2016-08-31 | 日立化成株式会社 | 感光性粘接剂组合物、膜状粘接剂、粘接片、粘接剂图形、半导体晶片和半导体装置 |
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JP6045772B2 (ja) * | 2008-08-27 | 2016-12-14 | 日立化成株式会社 | 感光性接着剤組成物、フィルム状接着剤、接着シート、接着剤パターン、接着剤層付半導体ウェハ、半導体装置、及び半導体装置の製造方法 |
EP2319892A4 (en) * | 2008-08-27 | 2012-01-18 | Hitachi Chemical Co Ltd | PHOTOSENSITIVE ADHESIVE COMPOSITION, PHOTOSENSITIVE FILM ADHESIVE, ADHESIVE PATTERN, SEMICONDUCTOR WAFER WITH ADHESIVE, SEMICONDUCTOR DEVICE, AND ELECTRONIC COMPONENT |
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JP5691228B2 (ja) * | 2009-04-07 | 2015-04-01 | 日立化成株式会社 | 感光性接着剤組成物、フィルム状接着剤、接着シート、接着剤パターン、接着剤層付半導体ウェハ、半導体装置、及び、半導体装置の製造方法 |
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