JPWO2017188153A1 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JPWO2017188153A1 JPWO2017188153A1 JP2017522685A JP2017522685A JPWO2017188153A1 JP WO2017188153 A1 JPWO2017188153 A1 JP WO2017188153A1 JP 2017522685 A JP2017522685 A JP 2017522685A JP 2017522685 A JP2017522685 A JP 2017522685A JP WO2017188153 A1 JPWO2017188153 A1 JP WO2017188153A1
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- 230000001502 supplementing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—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
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3205—Deposition of non-insulating-, e.g. conductive- or resistive-, layers on insulating layers; After-treatment of these layers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/70—Manufacture or treatment of devices consisting of a plurality of solid state components formed in or on a common substrate or of parts thereof; Manufacture of integrated circuit devices or of parts thereof
- H01L21/71—Manufacture of specific parts of devices defined in group H01L21/70
- H01L21/768—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
- H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
- H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
- H01L23/532—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body characterised by the materials
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- 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
- H01L2224/02—Bonding areas; Manufacturing methods related thereto
- H01L2224/04—Structure, shape, material or disposition of the bonding areas prior to the connecting process
- H01L2224/04105—Bonding areas formed on an encapsulation of the semiconductor or solid-state body, e.g. bonding areas on chip-scale packages
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- 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
- H01L2224/10—Bump connectors; Manufacturing methods related thereto
- H01L2224/12—Structure, shape, material or disposition of the bump connectors prior to the connecting process
- H01L2224/12105—Bump connectors formed on an encapsulation of the semiconductor or solid-state body, e.g. bumps on chip-scale packages
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- 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
- H01L2224/18—High density interconnect [HDI] connectors; Manufacturing methods related thereto
- H01L2224/19—Manufacturing methods of high density interconnect preforms
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Formation Of Insulating Films (AREA)
Abstract
(A)ポリベンゾオキサゾール前駆体、ポリイミド前駆体、ポリアミドイミド前駆体、およびそれらの共重合体、から選ばれる1種類以上を含んでなり、かつベンゾオキサゾール前駆体構造および脂肪族基を有するアルカリ可溶性樹脂、ならびに、
(B)熱酸発生剤および(E)酸化防止剤を含有する、樹脂組成物。
【選択図】なし
Description
(A)ポリベンゾオキサゾール前駆体、ポリイミド前駆体、ポリアミドイミド前駆体、およびそれらの共重合体、から選ばれる1種類以上を含んでなり、かつベンゾオキサゾール前駆体構造および脂肪族基を有するアルカリ可溶性樹脂、ならびに、
(B)熱酸発生剤および(E)酸化防止剤を含有する、樹脂組成物である。
次に記すアルカリ水溶液に浸漬した場合の溶解速度が50nm/分以上であることをいう。詳細には、γ−ブチロラクトンに樹脂を溶解した溶液をシリコンウエハ上に塗布し、120℃で4分間プリベークを行って膜厚10μm±0.5μmのプリベーク膜を形成し、前記プリベーク膜を23±1℃の2.38質量%テトラメチルアンモニウムヒドロキシド水溶液に1分間浸漬した後、純水でリンス処理したときの膜厚減少から求められる溶解速度が50nm/分以上であることをいう。
また、(A)成分は、ベンゾオキサゾール前駆体構造を有する。ベンゾオキサゾール前駆体構造を有することで、感光性能が向上するとともに、(A)成分を含有する樹脂組成物を硬化した硬化膜に対して高伸度性を付与でき、さらに、ベンゾオキサゾール前駆体が閉環することで、耐熱性、耐薬品性が向上する。
(A)成分が、脂肪族基を有することにより、(A)成分を含有する樹脂組成物を硬化した硬化膜が高伸度性を有するものとなる。また、(A)成分が脂肪族基を有することにより、樹脂に柔軟性が生まれ、樹脂のベンゾオキサゾール前駆体構造が閉環する場合に発生する応力の増加を抑制できる。このため、ベンゾオキサゾール前駆体構造の脱水閉環に伴う基板ウエハへの応力の増加を抑制することができる。また、脂肪族基は低紫外線吸収性であるため、その導入によりi線透過性が向上し高感度化も同時に実現できる。
一般式(3)および(4)中、R20〜R22はそれぞれ独立に炭素数1〜12の脂肪族基、または炭素数4〜12の芳香族基を示すが、脂肪族基および芳香族基はその一部の水素原子が置換されていてもよく、置換基としては、アルキル基、アシル基、フッ素基などのハロゲン基が挙げられる。
(C)熱架橋剤が上記一般式(5)で表される構造単位を有することにより、熱架橋剤自体に、柔軟なアルキレン基と剛直な芳香族基を有するため、耐熱性を有しながら、得られる硬化膜の伸度向上と低応力化が可能である。架橋基としては、アクリル基やメチロール基、アルコキシメチル基、エポキシ基が上げられるがこれに限定されない。この中でも、(A)成分のフェノール性水酸基と反応し、硬化膜の耐熱性を向上することができる点と、脱水せずに反応することができる点から、エポキシ基が好ましい。
上記構造の中でも、耐熱性と伸度向上を両立する点から、mは1〜2、lは3〜7であることが好ましい。
一般式(6)で表される化合物は、例としては以下のものが挙げられるが、これに限定されない。
一般式(7)で表される化合物を含有することで、加熱硬化後の膜と金属材料、とりわけ銅との密着性を著しく向上させ、剥離を抑制することができる。これは、一般式(7)で表される化合物のS原子やN原子が金属表面と効率良く相互作用することに由来しており、さらに金属面と相互作用しやすい立体構造となっていることに起因する。これらの効果により、本発明の樹脂組成物は、金属材料との接着性に優れた硬化膜を得ることができる。
図4に示すように、基板12には絶縁膜13、その上にパターンとして絶縁膜14が形成される。基板12としてはフェライト等が用いられる。本発明の感光性を有する樹脂組成物は絶縁膜13と絶縁膜14のどちらに使用してもよい。このパターンの開口部に金属(Cr、Ti等)膜15が形成され、この上に金属配線(Ag、Cu等)16がめっき形成される。金属配線16(Ag、Cu等)はスパイラル上に形成されている。13〜16を形成する工程を複数回繰り返し、積層させることでコイルとしての機能を持たせることができる。最後に金属配線16(Ag、Cu等)は金属配線17(Ag、Cu等)によって電極18に接続され、封止樹脂19により封止される。
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT−8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH−21CD−S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行った。温度が50℃以下になったところでシリコンウエハを取り出し、硬化膜(A)を得た。また、300〜350℃で加熱した硬化膜(B)を得た。これらの硬化膜(A)、および硬化膜(B)の赤外吸収スペクトルを測定し、1050cm−1付近のC−O伸縮振動に起因するピークの吸光度を求めた。赤外吸収スペクトルの測定は、測定装置として「FT−720」(商品名、株式会社堀場製作所製)を使用した。硬化膜(B)の閉環率を100%として、次の式から硬化膜(A)の閉環率を算出した。ここでいう閉環率とは、ポリ(o−ヒドロキシアミド)構造単位の閉環率のことである。
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT−8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH−21CD−S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行った。温度が50℃以下になったところでシリコンウエハを取り出し、45質量%のフッ化水素酸に5分間浸漬することで、ウエハより樹脂組成物の硬化膜を剥がした。この膜を幅0.5cm、長さ10cmの短冊状に切断し、熱重量測定装置TGDTA6200((株)日立ハイテクサイエンス製)を用いて、室温から400℃まで昇温速度10℃/分で加熱した際の5%重量減少温度を測定した。
ワニスを、シリコンウエハ上に120℃で3分間プリベークを行った後の膜厚が10μmとなるように塗布現像装置ACT−8を用いてスピンコート法で塗布し、プリベークした後、イナートオーブンCLH−21CD−Sを用いて、窒素気流下において酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行なった。温度が50℃以下になったところでシリコンウエハを取り出し、その硬化膜を有機薬液(ジメチルスルホキシド:25%水酸化テトラメチルアンモニウム水溶液=92:2)に65℃で100分間浸漬させ、パターンの剥がれや溶出の有無を観察した。
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT−8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH−21CD−S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で4.0℃/分で200℃または220℃まで昇温し、200℃または220℃で1時間加熱処理を行なった。温度が50℃以下になったところでシリコンウエハを取り出し、45質量%のフッ化水素酸に5分間浸漬することで、ウエハより樹脂組成物の硬化膜を剥がした。この膜を幅1cm、長さ9cmの短冊状に切断し、テンシロンRTM−100((株)オリエンテック製)を用いて、室温23.0℃、湿度45.0%RH下で引張速度50mm/分で引っ張り、破断点伸度の測定を行なった。測定は1検体につき10枚の短冊について行ない、結果から上位5点の平均値を求めた。
銅配線での剥離評価を行うにあたり、以下の評価基板を準備した。
2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(セントラル硝子(株)製、以下、BAHFとする。)18.3g(0.05モル)をアセトン100mL、プロピレンオキシド(東京化成(株)製)17.4g(0.3モル)に溶解させ、−15℃に冷却した。ここに3−ニトロベンゾイルクロリド(東京化成(株)製)20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、−15℃で4時間撹拌し、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、3,3’,4,4’−ジフェニルエーテルテトラカルボン酸二無水物(以降ODPAと呼ぶ)31.0g(0.10モル)をNMP500gに溶解させた。ここに合成例1で得られたヒドロキシル基含有ジアミン化合物39.30g(0.065モル)と1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)をNMP50gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。続いて、プロピレンオキシド及びテトラメチレンエーテルグリコール構造を含むRT−1000(10.00g、0.010モル)をNMP10gとともに加えて、50℃で1時間反応させた。次に末端封止剤として4−アミノフェノール4.36g(0.04モル)をNMP5gとともに加え、50℃で2時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール28.6g(0.24モル)をNMP50gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のアルカリ可溶性樹脂であるポリイミド前駆体(A−1)を得た。
乾燥窒素気流下、BAHF27.47g、(0.075モル)をNMP257gに溶解させた。ここに、1,1’−(4,4’−オキシベンゾイル)ジイミダゾール(以降PBOMと呼ぶ)(17.20g、0.048モル)をNMP20gとともに加えて、85℃で3時間反応させた。続いて、プロピレンオキシド及びテトラメチレンエーテルグリコール構造を含むRT−1000(20.00g、0.020モル)、1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン(1.24g、0.005モル)、PBOM(14.33g、0.044モル)をNMP50gとともに加えて、85℃で1時間反応させた。さらに、末端封止剤として、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)をNMP10gとともに加えて、85℃で30分反応させた。反応終了後、室温まで冷却し、酢酸(52.82g、0.50モル)をNMP87gとともに加えて、室温で1時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリベンゾオキサゾール前駆体(A−2)の粉末を得た。
前記合成例3に従って、BAHF(27.47g、0.075モル)、PBOM(30.10g、0.084モル)、プロピレンオキシド及びエチレングリコール構造を含むED−900(9.00g、0.020モル)、1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(5.25g、0.032モル)、酢酸(48.02g、0.80モル)、NMP409gを用いて同様に行い、ポリベンゾオキサゾール前駆体(A−3)の粉末を得た。
前記合成例3に従って、BAHF(32.96g、0.090モル)、PBOM(29.38g、0.082モル)、RT−1000(10.00g、0.010モル)、1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン(1.49g、0.0060モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(5.91g、0.036モル)、HFHA(0.60g、0.0010モル)、ODPA(2.17g、0.0070モル)、酢酸(49.22g、0.82モル)、NMP360gを用いて同様に行い、ポリベンゾオキサゾール前駆体(A−4)の粉末を得た。
乾燥窒素気流下、無水ジフェニルエーテルトリカルボン酸クロリド27.5g(0.10モル)をNMP500gに溶解させた。ここに合成例1で得られたヒドロキシル基含有ジアミン化合物39.30g(0.065モル)と1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)をNMP50gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。続いて、プロピレンオキシド及びテトラメチレンエーテルグリコール構造を含むRT−1000(10.00g、0.010モル)をNMP10gとともに加えて、50℃で1時間反応させた。次に末端封止剤として4−アミノフェノール4.36g(0.04モル)をNMP5gとともに加え、50℃で2時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール28.6g(0.24モル)をNMP50gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリアミドイミド前駆体(A−5)を得た。
得られた(A)成分(A−1〜5)10gに(B)熱酸発生剤として3−(5−(((フェニルスルホニルオキシ)イミノ)チオフェン−2(5H)−イリデン−2−(o−トリル)プロパンニトリル(B−1)を0.2g(0.52ミリモル)、またはSI−200(B−2)を0.2g(0.53ミリモル)、(C)熱架橋剤としてHMOM−TPHAP(C−1)を2.4g(4.2ミリモル)とMW−100LM(C−2)を1.0g(2.6ミリモル)、(D)感光性化合物として下記式で表される感光性化合物を2.0g(1.8ミリモル)加え、溶剤としてγ−ブチロラクトンを20g加えてワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表1に示す。
(B)熱酸発生剤を用いない以外は参考例1〜15と同様にワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表1に示す。
得られた(A)成分(A−1〜5)10gに(B)熱酸発生剤として3−(5−(((フェニルスルホニルオキシ)イミノ)チオフェン−2(5H)−イリデン−2−(o−トリル)プロパンニトリル(B−1)を0.2g(0.52ミリモル)、またはSI−200(B−2)を0.2g(0.53ミリモル)、または0.5g(1.3ミリモル)、または0.8g(2.1ミリモル)(C)熱架橋剤としてHMOM−TPHAP(C−1)を2.4g(4.2ミリモル)とMW−100LM(C−2)を1.0g(2.6ミリモル)、または下記式で表される熱架橋剤(C−3)を0.2g(0.25ミリモル)、または1.5g(1.9ミリモル)、または5.1g(6.5ミリモル)(D)感光性化合物として下記式で表される感光性化合物を2.0g(1.8ミリモル)、(E)酸化防止剤として下記式で表される化合物(E−1)を0.15g(0.26ミリモル)または(E−2)を0.15g(0.27ミリモル)加え、溶剤としてγ−ブチロラクトンを20g加えてワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表2に示す。
(B)熱酸発生剤を用いない以外は比較例2および6〜9と同様にワニスを作製(比較例10〜14)、または、(B)熱酸発生剤としてSI−200(B−2)を1.2g(3.2ミリモル)加えた以外は比較例2と同様にワニスを作製(比較例15)し、これらの特性を上記評価方法により測定した。得られた結果を表2に示す。
2 Alパッド
3 パッシベーション膜
4 絶縁膜
5 金属(Cr、Ti等)膜
6 金属配線(Al、Cu等)
7 絶縁膜
8 バリアメタル
9 スクライブライン
10 ハンダバンプ
11 封止樹脂
12 基板
13 絶縁膜
14 絶縁膜
15 金属(Cr、Ti等)膜
16 金属配線(Ag、Cu等)
17 金属配線(Ag、Cu等)
18 電極
19 封止樹脂
Claims (20)
- (A)ポリベンゾオキサゾール前駆体、ポリイミド前駆体、ポリアミドイミド前駆体、およびそれらの共重合体、から選ばれる1種類以上を含んでなり、かつベンゾオキサゾール前駆体構造および脂肪族基を有するアルカリ可溶性樹脂、ならびに、
(B)熱酸発生剤および(E)酸化防止剤を含有する、樹脂組成物。 - 前記(A)ポリベンゾオキサゾール前駆体、ポリイミド前駆体、ポリアミドイミド前駆体、およびそれらの共重合体、から選ばれる1種類以上を含んでなり、かつベンゾオキサゾール前駆体構造および脂肪族基を有するアルカリ可溶性樹脂が、
一般式(1)で表される構造単位を有する、請求項1に記載の樹脂組成物。
- 前記脂肪族基が、アルキレン基およびオキシアルキレン基のうち少なくともいずれかの有機基を有する、請求項1または2に記載の樹脂組成物。
- 前記脂肪族基が、下記一般式(2)で表される、請求項1〜3のいずれかに記載の樹脂組成物。
- 前記一般式(1)におけるYが、下記一般式(2)で表される脂肪族基を有する、請求項2に記載の樹脂組成物。
- 前記(B)熱酸発生剤が、下記一般式(3)で表されるスルホン酸エステル化合物、一般式(4)で表されるスルホン酸エステル化合物、およびオニウム塩、から選ばれる1種類以上の化合物を含む、請求項1〜5のいずれかに記載の樹脂組成物。
- 前記(B)熱酸発生剤の熱分解開始温度が、140℃以上220℃以下である、請求項1〜6のいずれかに記載の樹脂組成物。
- さらに、(C)熱架橋剤および(D)感光性化合物を含有する、請求項1〜7のいずれかに記載の樹脂組成物。
- 前記(C)熱架橋剤が、一般式(5)で表される構造単位を有する熱架橋剤を含む、請求項8に記載の樹脂組成物。
- 前記(E)酸化防止剤が、一般式(6)で表される化合物を含有する、請求項1〜9のいずれかに記載の樹脂組成物。
- 請求項1〜10のいずれかに記載の樹脂組成物から形成された樹脂シート。
- 請求項1〜10のいずれかに記載の樹脂組成物を硬化した硬化膜。
- 請求項11に記載の樹脂シートを硬化した硬化膜。
- ベンゾオキサゾール前駆体構造がポリベンゾオキサゾールに閉環している割合が30%以上である、請求項12または13に記載の硬化膜。
- 請求項1〜10のいずれかに記載の樹脂組成物を基板上に塗布し、または請求項11に記載の樹脂シートを基材上にラミネートし、乾燥して樹脂膜を形成する工程、
乾燥した樹脂膜を露光する露光工程、露光した樹脂膜を現像する現像工程、
および現像した樹脂膜を加熱処理する加熱処理工程を含むことを特徴とする硬化膜の製造方法。 - 前記現像した樹脂膜を加熱処理する加熱処理工程が、140℃以上220℃以下で加熱処理する工程を含む、請求項15に記載の硬化膜の製造方法。
- 請求項12〜14のいずれかに記載の硬化膜が配置された、層間絶縁膜または半導体保護膜。
- 請求項12〜14のいずれかに記載の硬化膜が再配線の間の層間絶縁膜として配置された、半導体電子部品または半導体装置。
- 前記再配線と層間絶縁膜が2〜10層繰り返し配置された、請求項18に記載の半導体電子部品または半導体装置。
- 請求項12〜14のいずれかに記載の硬化膜が2種以上の材料で構成される隣接する基板の層間絶縁膜として配置された、半導体電子部品または半導体装置。
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