JP2021195447A - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JP2021195447A JP2021195447A JP2020102580A JP2020102580A JP2021195447A JP 2021195447 A JP2021195447 A JP 2021195447A JP 2020102580 A JP2020102580 A JP 2020102580A JP 2020102580 A JP2020102580 A JP 2020102580A JP 2021195447 A JP2021195447 A JP 2021195447A
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- LTURHSAEWJPFAA-UHFFFAOYSA-N sulfuric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OS(O)(=O)=O.NC1=NC(N)=NC(N)=N1 LTURHSAEWJPFAA-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
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- KAAYGTMPJQOOGY-UHFFFAOYSA-N tris(2,5-dimethylphenyl)phosphane Chemical compound CC1=CC=C(C)C(P(C=2C(=CC=C(C)C=2)C)C=2C(=CC=C(C)C=2)C)=C1 KAAYGTMPJQOOGY-UHFFFAOYSA-N 0.000 description 1
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 description 1
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- XRALRSQLQXKXKP-UHFFFAOYSA-N tris(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 XRALRSQLQXKXKP-UHFFFAOYSA-N 0.000 description 1
- RYXYUARTMQUYKV-UHFFFAOYSA-N tris(4-butylphenyl)phosphane Chemical compound C1=CC(CCCC)=CC=C1P(C=1C=CC(CCCC)=CC=1)C1=CC=C(CCCC)C=C1 RYXYUARTMQUYKV-UHFFFAOYSA-N 0.000 description 1
- SPNVODOGUAUMCA-UHFFFAOYSA-N tris(4-ethoxy-2,6-dimethylphenyl)phosphane Chemical compound CC1=CC(OCC)=CC(C)=C1P(C=1C(=CC(OCC)=CC=1C)C)C1=C(C)C=C(OCC)C=C1C SPNVODOGUAUMCA-UHFFFAOYSA-N 0.000 description 1
- LQEKTSMTEYLBLJ-UHFFFAOYSA-N tris(4-ethoxyphenyl)phosphane Chemical compound C1=CC(OCC)=CC=C1P(C=1C=CC(OCC)=CC=1)C1=CC=C(OCC)C=C1 LQEKTSMTEYLBLJ-UHFFFAOYSA-N 0.000 description 1
- PCCAGZSOGFNURV-UHFFFAOYSA-N tris(4-ethylphenyl)phosphane Chemical compound C1=CC(CC)=CC=C1P(C=1C=CC(CC)=CC=1)C1=CC=C(CC)C=C1 PCCAGZSOGFNURV-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- NTUMNRFLAZXNBW-UHFFFAOYSA-N tris(4-propan-2-ylphenyl)phosphane Chemical compound C1=CC(C(C)C)=CC=C1P(C=1C=CC(=CC=1)C(C)C)C1=CC=C(C(C)C)C=C1 NTUMNRFLAZXNBW-UHFFFAOYSA-N 0.000 description 1
- JTOQWGJGVSYTTN-UHFFFAOYSA-N tris(4-propylphenyl)phosphane Chemical compound C1=CC(CCC)=CC=C1P(C=1C=CC(CCC)=CC=1)C1=CC=C(CCC)C=C1 JTOQWGJGVSYTTN-UHFFFAOYSA-N 0.000 description 1
- UQHFPPSBVOIUFM-UHFFFAOYSA-N tris(4-tert-butylphenyl)phosphane Chemical compound C1=CC(C(C)(C)C)=CC=C1P(C=1C=CC(=CC=1)C(C)(C)C)C1=CC=C(C(C)(C)C)C=C1 UQHFPPSBVOIUFM-UHFFFAOYSA-N 0.000 description 1
- UGNAOCDIZFIEQK-UHFFFAOYSA-N tris[4-[(2-methylpropan-2-yl)oxy]phenyl]phosphane Chemical compound C1=CC(OC(C)(C)C)=CC=C1P(C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 UGNAOCDIZFIEQK-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910000859 α-Fe Inorganic materials 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
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
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- C08K7/00—Use of ingredients characterised by shape
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- C08K7/18—Solid spheres inorganic
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- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
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- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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- C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
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- C08J2325/08—Copolymers of styrene
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- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
[1] (A)環状イミノエーテル骨格含有ポリスチレン樹脂、(B)硬化剤、及び(C)無機充填材を含む樹脂組成物。
[2] (A)成分が、オキサゾリン骨格含有ポリスチレン樹脂を含む、上記[1]に記載の樹脂組成物。
[3] (A)成分が、式(1):
で表される繰り返し単位、及び式(2):
で表される繰り返し単位を有する樹脂を含む、上記[1]又は[2]に記載の樹脂組成物。
[4] (A)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、50質量%以下である、上記[1]〜[3]の何れかに記載の樹脂組成物。
[5] (B)成分が、(B−1)フェノール系硬化剤、(B−2)酸無水物系硬化剤、及び(B−3)カルボン酸系硬化剤から選ばれる硬化剤を含む、上記[1]〜[4]の何れかに記載の樹脂組成物。
[6] (A)成分の環状イミノエーテル骨格に対する(B)成分の反応基のモル当量比((B)成分の反応基/(A)成分の環状イミノエーテル骨格)が、1以下である、上記[1]〜[5]の何れかに記載の樹脂組成物。
[7] (A)成分に対する(B)成分の質量比((B)成分/(A)成分)は、0.01〜1である、上記[1]〜[6]の何れかに記載の樹脂組成物。
[8] (C)成分が、シリカである、上記[1]〜[7]の何れかに記載の樹脂組成物。
[9] (C)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、40質量%以上である、上記[1]〜[8]の何れかに記載の樹脂組成物。
[10] (C)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、70質量%以下である、上記[1]〜[9]の何れかに記載の樹脂組成物。
[11] (A)成分に対する(C)成分の質量比((C)成分/(A)成分)が、0.5〜10である、上記[1]〜[10]の何れかに記載の樹脂組成物。
[12] さらに(D)エポキシ樹脂を含む、上記[1]〜[11]の何れかに記載の樹脂組成物。
[13] さらに(G)ベンゾシクロブテン樹脂を含む、上記[1]〜[12]の何れかに記載の樹脂組成物。
[14] 樹脂組成物の硬化物(硬化温度200℃)の誘電正接が、5.8GHz、23℃で測定した場合、0.004以下である、上記[1]〜[13]の何れかに記載の樹脂組成物。
[15] 樹脂組成物の硬化物(硬化温度200℃)の比誘電率が、5.8GHz、23℃で測定した場合、3.0以下である、上記[1]〜[14]の何れかに記載の樹脂組成物。
[16] プリント配線板の絶縁層を形成するための上記[1]〜[15]の何れかに記載の樹脂組成物。
[17] 上記[1]〜[16]の何れかに記載の樹脂組成物の硬化物。
[18] 上記[1]〜[16]の何れかに記載の樹脂組成物を含有する、シート状積層材料。
[19] 支持体と、当該支持体上に設けられた上記[1]〜[16]の何れかに記載の樹脂組成物から形成される樹脂組成物層と、を有する樹脂シート。
[20] 上記[1]〜[16]の何れかに記載の樹脂組成物の硬化物からなる絶縁層を備えるプリント配線板。
[21] 上記[20]に記載のプリント配線板を含む、半導体装置。
本発明の樹脂組成物は、(A)環状イミノエーテル骨格含有ポリスチレン樹脂、(B)硬化剤、及び(C)無機充填材を含む。このような樹脂組成物を用いることにより、比誘電率(Dk)及び誘電正接(Df)が低く抑えられた硬化物を得ることができる。
本発明の樹脂組成物は、(A)環状イミノエーテル骨格含有ポリスチレン樹脂を含有する。(A)成分は、1種類単独で用いてもよく、2種類以上を任意に組み合わせて用いてもよい。
で表される繰り返し単位、及び式(2):
で表される繰り返し単位を有する樹脂を含む。
で表される繰り返し単位であり、より好ましくは、式(2’’−1)〜(2’’−20):
本発明の樹脂組成物は、(B)硬化剤を含有する。(B)硬化剤は、1種類単独で用いてもよく、2種類以上を任意に組み合わせて用いてもよい。ここで説明する(B)硬化剤は、一実施形態において、少なくとも(A)環状イミノエーテル骨格含有ポリスチレン樹脂と反応(例えば付加反応)して樹脂組成物を硬化する機能を有する。また、(B)硬化剤は、一実施形態において、樹脂組成物が(D)エポキシ樹脂等を含む場合、(A)成分に加えて(D)成分等と反応(例えば付加反応)して樹脂組成物を硬化する機能を有する場合がある。
本発明の樹脂組成物は、(C)無機充填材を含有する。(C)無機充填材は、粒子の状態で樹脂組成物に含まれる。
本発明の樹脂組成物は、任意成分として(D)エポキシ樹脂を含む場合がある。(D)エポキシ樹脂とは、エポキシ基を有する硬化性樹脂を意味する。
本発明の樹脂組成物は、(D)エポキシ樹脂を含む場合、任意成分として、さらに(E)エポキシ硬化剤を含む場合がある。ここで説明する(E)エポキシ硬化剤は、一実施形態において、(D)エポキシ樹脂が上記で説明した(B)硬化剤と反応しない或いは反応速度が劣り十分反応しない場合に、(D)エポキシ樹脂と十分に反応(例えば付加反応)して樹脂組成物を硬化する。(E)エポキシ硬化剤は、一実施形態において、(D)成分との反応速度に比べて(A)成分との反応速度が遅く或いは反応しない。(E)エポキシ硬化剤は1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の樹脂組成物は、(D)エポキシ樹脂を含む場合、任意成分として、さらに(F)エポキシ硬化促進剤を含む場合がある。一実施形態において、(F)エポキシ硬化促進剤は、(D)エポキシ樹脂の硬化反応を促進する触媒としての機能を有し得る。
(F−2)アミン系硬化促進剤、(F−3)リン系硬化促進剤、(F−4)ウレア系硬化促進剤、(F−5)グアニジン系硬化促進剤、(F−6)金属系硬化促進剤等が挙げられる。一実施形態において、(F)エポキシ硬化促進剤は、(F−1)イミダゾール系硬化促進剤及び(F−2)アミン系硬化促進剤から選ばれるエポキシ硬化促進剤を含むことが好ましい。(F)エポキシ硬化促進剤は、1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の樹脂組成物は、任意成分として、(G)ベンゾシクロブテン樹脂を含む場合がある。(G)ベンゾシクロブテン樹脂は、1個以上のベンゾシクロブテン環、好ましくは、2個以上のベンゾシクロブテン環を有する化合物である。一実施形態において、(G)成分は、エチレン性不飽和基と付加反応し得る。
で表される樹脂である。
本発明の樹脂組成物は、不揮発成分として、さらに任意の添加剤を含んでいてもよい。このような添加剤としては、例えば、マレイミド系ラジカル重合性化合物、ビニルフェニル系ラジカル重合性化合物、(メタ)アクリル系ラジカル重合性化合物、アリル系ラジカル重合性化合物、ポリブタジエン系ラジカル重合性化合物等のラジカル重合性化合物;過酸化物系ラジカル重合開始剤、アゾ系ラジカル重合開始剤等のラジカル重合開始剤;ポリビニルアセタール樹脂、ポリオレフィン樹脂、ポリスルホン樹脂、ポリエーテルスルホン樹脂、ポリフェニレンエーテル樹脂、ポリカーボネート樹脂、ポリエーテルエーテルケトン樹脂、ポリエステル樹脂等の熱可塑性樹脂;エポキシアクリレート樹脂、ウレタンアクリレート樹脂、ウレタン樹脂、シアネート樹脂、ポリイミド樹脂、ベンゾオキサジン樹脂、不飽和ポリエステル樹脂、フェノール樹脂、メラミン樹脂、シリコーン樹脂、フェノキシ樹脂等のエポキシ樹脂以外の熱硬化性樹脂;ゴム粒子等の有機充填材;有機銅化合物、有機亜鉛化合物、有機コバルト化合物等の有機金属化合物;フタロシアニンブルー、フタロシアニングリーン、アイオディングリーン、ジアゾイエロー、クリスタルバイオレット、酸化チタン、カーボンブラック等の着色剤;ハイドロキノン、カテコール、ピロガロール、フェノチアジン等の重合禁止剤;シリコーン系レベリング剤、アクリルポリマー系レベリング剤等のレベリング剤;ベントン、モンモリロナイト等の増粘剤;シリコーン系消泡剤、アクリル系消泡剤、フッ素系消泡剤、ビニル樹脂系消泡剤等の消泡剤;ベンゾトリアゾール系紫外線吸収剤等の紫外線吸収剤;尿素シラン等の接着性向上剤;トリアゾール系密着性付与剤、テトラゾール系密着性付与剤、トリアジン系密着性付与剤等の密着性付与剤;ヒンダードフェノール系酸化防止剤、ヒンダードアミン系酸化防止剤等の酸化防止剤;スチルベン誘導体等の蛍光増白剤;フッ素系界面活性剤、シリコーン系界面活性剤等の界面活性剤;リン系難燃剤(例えばリン酸エステル化合物、ホスファゼン化合物、ホスフィン酸化合物、赤リン)、窒素系難燃剤(例えば硫酸メラミン)、ハロゲン系難燃剤、無機系難燃剤(例えば三酸化アンチモン)等の難燃剤;リン酸エステル系分散剤、ポリオキシアルキレン系分散剤、アセチレン系分散剤、シリコーン系分散剤、アニオン性分散剤、カチオン性分散剤等の分散剤;ボレート系安定剤、チタネート系安定剤、アルミネート系安定剤、ジルコネート系安定剤、イソシアネート系安定剤、カルボン酸系安定剤、カルボン酸無水物系安定剤等の安定剤等が挙げられる。(H)その他の添加剤は、1種を単独で用いてもよく、2種以上を任意の比率で組み合わせて用いてもよい。(H)その他の添加剤の含有量は当業者であれば適宜設定できる。
本発明の樹脂組成物は、上述した不揮発性成分以外に、揮発性成分として、さらに任意の有機溶剤を含有する場合がある。(I)有機溶剤としては、不揮発性成分の少なくとも一部を溶解可能なものである限り、公知のものを適宜用いることができ、その種類は特に限定されるものではない。(I)有機溶剤としては、例えば、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶剤;酢酸メチル、酢酸エチル、酢酸ブチル、酢酸イソブチル、酢酸イソアミル、プロピオン酸メチル、プロピオン酸エチル、γ-ブチロラクトン等のエステル系溶剤;テトラヒドロピラン、テトラヒドロフラン、1,4−ジオキサン、ジエチルエーテル、ジイソプロピルエーテル、ジブチルエーテル、ジフェニルエーテル等のエーテル系溶剤;メタノール、エタノール、プロパノール、ブタノール、エチレングリコール等のアルコール系溶剤;酢酸2−エトキシエチル、プロピレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセタート、エチルジグリコールアセテート、γ−ブチロラクトン、メトキシプロピオン酸メチル等のエーテルエステル系溶剤;乳酸メチル、乳酸エチル、2−ヒドロキシイソ酪酸メチル等のエステルアルコール系溶剤;2−メトキシプロパノール、2−メトキシエタノール、2−エトキシエタノール、プロピレングリコールモノメチルエーテル、ジエチレングリコールモノブチルエーテル(ブチルカルビトール)等のエーテルアルコール系溶剤;N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチル−2−ピロリドン等のアミド系溶剤;ジメチルスルホキシド等のスルホキシド系溶剤;アセトニトリル、プロピオニトリル等のニトリル系溶剤;ヘキサン、シクロペンタン、シクロヘキサン、メチルシクロヘキサン等の脂肪族炭化水素系溶剤;ベンゼン、トルエン、キシレン、エチルベンゼン、トリメチルベンゼン等の芳香族炭化水素系溶剤等を挙げることができる。(I)有機溶剤は、1種単独で用いてもよく、2種以上を任意の比率で組み合わせて用いてもよい。(I)有機溶剤は、使用する場合、1種単独で用いてもよく、2種以上を任意の比率で組み合わせて用いてもよい。
本発明の樹脂組成物は、例えば、任意の調製容器に、(A)環状イミノエーテル骨格含有ポリスチレン樹脂、(B)硬化剤、(C)無機充填材、必要に応じて(D)エポキシ樹脂、必要に応じて(E)エポキシ硬化剤、必要に応じて(F)エポキシ硬化促進剤、必要に応じて(G)ベンゾシクロブテン樹脂、必要に応じて(H)その他の添加剤、及び必要に応じて(I)有機溶剤を、任意の順で及び/又は一部若しくは全部同時に加えて混合することによって、製造することができる。また、各成分を加えて混合する過程で、温度を適宜設定することができ、一時的に又は終始にわたって、加熱及び/又は冷却してもよい。また、加えて混合する過程において又はその後に、樹脂組成物を、例えば、ミキサーなどの撹拌装置又は振盪装置を用いて撹拌又は振盪し、均一に分散させてもよい。また、撹拌又は振盪と同時に、真空下等の低圧条件下で脱泡を行ってもよい。
本発明の樹脂組成物は、(A)環状イミノエーテル骨格含有ポリスチレン樹脂、(B)硬化剤、及び(C)無機充填材を含む。このような樹脂組成物を用いることにより、比誘電率(Dk)及び誘電正接(Df)が低く抑えられた硬化物を得ることができる。また、一実施形態において、このような樹脂組成物を用いることにより、銅密着性が優れた硬化物を得ることができ得る。
本発明の樹脂組成物は、絶縁用途の樹脂組成物、特に、絶縁層を形成するための樹脂組成物として好適に使用することができる。具体的には、絶縁層上に形成される導体層(再配線層を含む)を形成するための当該絶縁層を形成するための樹脂組成物(導体層を形成するための絶縁層形成用樹脂組成物)として好適に使用することができる。また、後述するプリント配線板において、プリント配線板の絶縁層を形成するための樹脂組成物(プリント配線板の絶縁層形成用樹脂組成物)として好適に使用することができる。本発明の樹脂組成物はまた、樹脂シート、プリプレグ等のシート状積層材料、ソルダーレジスト、アンダーフィル材、ダイボンディング材、半導体封止材、穴埋め樹脂、部品埋め込み樹脂等、樹脂組成物が必要とされる用途で広範囲に使用できる。
(1)基材に仮固定フィルムを積層する工程、
(2)半導体チップを、仮固定フィルム上に仮固定する工程、
(3)半導体チップ上に封止層を形成する工程、
(4)基材及び仮固定フィルムを半導体チップから剥離する工程、
(5)半導体チップの基材及び仮固定フィルムを剥離した面に、絶縁層としての再配線形成層を形成する工程、及び
(6)再配線形成層上に、導体層としての再配線層を形成する工程
本発明の樹脂組成物は、ワニス状態で塗布して使用することもできるが、工業的には一般に、該樹脂組成物を含有するシート状積層材料の形態で用いることが好適である。
本発明のプリント配線板は、本発明の樹脂組成物を硬化して得られる硬化物からなる絶縁層を含む。
(I)内層基板上に、樹脂シートを、樹脂シートの樹脂組成物層が内層基板と接合するように積層する工程
(II)樹脂組成物層を硬化(例えば熱硬化)して絶縁層を形成する工程
本発明の半導体装置は、本発明のプリント配線板を含む。本発明の半導体装置は、本発明のプリント配線板を用いて製造することができる。
オキサゾリン基を含有したポリスチレン樹脂(日本触媒社製「RPS−1005」、活性基当量約3700g/eq.)50部をトルエン50部、シクロヘキサノン50部に撹拌しながら加熱溶解させた。
ベンゾシクロブテン樹脂(ダウ・ケミカル社製「CYCLOTEN3022」)12部をさらに追加し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を110部から135部に変更した以外は、実施例1と同様にして、樹脂組成物を調製した。
ビスフェノールAF型エポキシ樹脂(三菱ケミカル社製「YX7760」、エポキシ当量約245g/eq.)8部、活性エステル系硬化剤(DIC社製「HPC−8000−65T」、活性基当量約223g/eq.、固形分65質量%のトルエン溶液)10部、及び硬化促進剤(1B2PZ(1−ベンジル−2−フェニルイミダゾール)の固形分10%のMEK溶液)0.5部をさらに追加し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を110部から140部に変更した以外は、実施例1と同様にして、樹脂組成物を調製した。
脂環式エポキシ樹脂(ダイセル社製「2021P」、エポキシ当量約137g/eq.)4部、活性エステル系硬化剤(DIC社製「HPC−8000−65T」、活性基当量約223g/eq.、固形分65質量%のトルエン溶液)10部、及び硬化促進剤(1B2PZ(1−ベンジル−2−フェニルイミダゾール)の固形分10%のMEK溶液)0.5部をさらに追加し、フェノール系硬化剤(SABIC社製「SA−90」、活性基当量約800g/eq.)10部の代わりに酸無水物系硬化剤(Polyscope社製「XIRAN EF30」、酸価約280g/eq.)を3.5部使用し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を110部から120部に変更した以外は、実施例1と同様にして、樹脂組成物を調製した。
脂環式エポキシ樹脂(ダイセル社製「2021P」、エポキシ当量約137g/eq.)4部の代わりにビスフェノール系エポキシ樹脂(日鉄ケミカル&マテリアル社製「ZX−1059」、エポキシ当量約165g/eq.)を5部使用し、活性エステル系硬化剤(DIC社製「HPC−8000−65T」、活性基当量約223g/eq.、固形分65質量%のトルエン溶液)10部の代わりに活性エステル系硬化剤(DIC社製「HPC−8150−62T」、活性基当量約229g/eq.、固形分62質量%のトルエン溶液)を10部使用した以外は、実施例4と同様にして、樹脂組成物を調製した。
フェノール系硬化剤(SABIC社製「SA−90」、活性基当量約800g/eq.)10部の代わりにエステル基含有カルボン酸系硬化剤(Polyscope社製「XIRAN 1440」、酸価約185g/eq.)を2.4部使用し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を110部から96部に変更した以外は、実施例1と同様にして、樹脂組成物を調製した。
ベンゾシクロブテン樹脂(ダウ・ケミカル社製「CYCLOTEN3022」)10部をさらに追加し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を96部から115部に変更した以外は、実施例6と同様にして、樹脂組成物を調製した。
ナフタレン型エポキシ樹脂(DIC社製「HP−4032SS」、エポキシ当量約144g/eq.)4部、活性エステル系硬化剤(DIC社製「HPC−8150−62T」、活性基当量約229g/eq.、固形分62質量%のトルエン溶液)10部、及び硬化促進剤(1B2PZ(1−ベンジル−2−フェニルイミダゾール)の固形分10%のMEK溶液)0.5部をさらに追加し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を96部から120部に変更した以外は、実施例6と同様にして、樹脂組成物を調製した。
N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を110部から140部に変更した以外は、実施例1と同様にして、樹脂組成物を調製した。
N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を110部から40部に変更した以外は、実施例1と同様にして、樹脂組成物を調製した。
オキサゾリン基を含有したポリスチレン樹脂(日本触媒社製「RPS−1005」、活性基当量約3700g/eq.)50部を使用せず、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を110部から120部に変更した以外は、実施例1と同様にして、樹脂組成物を調製した。
オキサゾリン基を含有したポリスチレン樹脂(日本触媒社製「RPS−1005」、活性基当量約3700g/eq.)50部の代わりにエポキシ樹脂(三菱ケミカル社製「1010」、エポキシ当量約4000g/eq.)を55部使用し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を140部から145部に変更した以外は、実施例3と同様にして、樹脂組成物を調製した。
オキサゾリン基を含有したポリスチレン樹脂(日本触媒社製「RPS−1005」、活性基当量約3700g/eq.)50部の代わりにエポキシ樹脂(三菱ケミカル社製「1010」、エポキシ当量約4000g/eq.)を55部使用し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を120部から130部に変更した以外は、実施例4と同様にして、樹脂組成物を調製した。
オキサゾリン基を含有したポリスチレン樹脂(日本触媒社製「RPS−1005」、活性基当量約3700g/eq.)50部の代わりにエポキシ樹脂(三菱ケミカル社製「1010」、エポキシ当量約4000g/eq.)を55部使用し、N−フェニル−8−アミノオクチル−トリメトキシシラン(信越化学工業社製、分子量325.2)で表面処理された球形シリカ(アドマテックス社製「SC2050−SXF」、比表面積5.9m2/g、平均粒径0.77μm)の使用量を96部から105部に変更した以外は、実施例6と同様にして、樹脂組成物を調製した。
無機充填材100mg、分散剤(サンノプコ社製「SN9228」)0.1g、メチルエチルケトン10gをバイアル瓶に秤取り、超音波にて20分間分散した。レーザー回折式粒径分布測定装置(島津製作所社製「SALD−2200」)を使用して、回分セル方式で粒径分布を測定し、メディアン径による平均粒径を算出した。
支持体として、アルキド樹脂系離型剤(リンテック社製「AL−5」)で離型処理を施したポリエチレンテレフタレートフィルム(東レ社製「ルミラーR80」、厚み38μm、軟化点130℃)を用意した。
(1)銅箔の下地処理
三井金属鉱山社製「3EC−III」(電界銅箔、35μm)の光沢面をマイクロエッチング剤((メック社製「CZ8101」)にて1μmエッチングして銅表面の粗化処理を行い、次いで防錆処理(CL8300)を施した。さらに、130℃のオーブンで30分間加熱処理した。この銅箔をCZ銅箔という。
内層回路を形成したガラス布基材エポキシ樹脂両面銅張積層板(銅箔の厚さ18μm、基板の厚さ0.4mm、パナソニック社製「R1515A」)の両面をマイクロエッチング剤(メック社製「CZ8101」)にて1μmエッチングして銅表面の粗化処理を行った。
試験例1で得た各樹脂シートから保護フィルムを剥がして、樹脂組成物層を露出させた。バッチ式真空加圧ラミネーター(ニッコー・マテリアルズ社製、2ステージビルドアップラミネーター「CVP700」)を用いて、樹脂組成物層が内層基板と接するように、内層基板の両面にラミネートした。ラミネートは、30秒間減圧して気圧を13hPa以下に調整した後、120℃、圧力0.74MPaにて30秒間圧着させることにより実施した。次いで、100℃、圧力0.5MPaにて60秒間熱プレスを行った。その樹脂組成物層上に、CZ銅箔の処理面を、上記と同様の条件で、ラミネートした。そして、200℃、90分の硬化条件で樹脂組成物層を硬化して絶縁層を形成することで、評価基板を作製した。また、実施例2及び7で調製した樹脂組成物から得られた樹脂シートに関しては、前者(200℃90分間硬化物)とは別に窒素雰囲気下220℃にて90分間加熱して樹脂組成物層を硬化して絶縁層を形成することで、評価基板をさらに作製した。
作製した評価基板を150×30mmの小片に切断した。小片の銅箔部分に、カッターを用いて幅10mm、長さ100mmの部分の切込みをいれて、銅箔の一端を剥がしてつかみ具で掴み、室温中にて、50mm/分の速度で垂直方向に35mmを引き剥がした時の荷重(kgf/cm)を測定し、剥離強度を求めた。測定には、引っ張り試験機(TSE社製「AC−50C−SL」)を使用した。測定は日本工業規格(JIS C6481)に準拠して行った。銅箔引き剥がし強度が0.4kgf/cm以上の場合を「〇」と評価し、その他の場合を「×」と評価した。
Claims (21)
- (A)環状イミノエーテル骨格含有ポリスチレン樹脂、(B)硬化剤、及び(C)無機充填材を含む樹脂組成物。
- (A)成分が、オキサゾリン骨格含有ポリスチレン樹脂を含む、請求項1に記載の樹脂組成物。
- (A)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、50質量%以下である、請求項1〜3の何れか1項に記載の樹脂組成物。
- (B)成分が、(B−1)フェノール系硬化剤、(B−2)酸無水物系硬化剤、及び(B−3)カルボン酸系硬化剤から選ばれる硬化剤を含む、請求項1〜4の何れか1項に記載の樹脂組成物。
- (A)成分の環状イミノエーテル骨格に対する(B)成分の反応基のモル当量比((B)成分の反応基/(A)成分の環状イミノエーテル骨格)が、1以下である、請求項1〜5の何れか1項に記載の樹脂組成物。
- (A)成分に対する(B)成分の質量比((B)成分/(A)成分)は、0.01〜1である、請求項1〜6の何れか1項に記載の樹脂組成物。
- (C)成分が、シリカである、請求項1〜7の何れか1項に記載の樹脂組成物。
- (C)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、40質量%以上である、請求項1〜8の何れか1項に記載の樹脂組成物。
- (C)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、70質量%以下である、請求項1〜9の何れか1項に記載の樹脂組成物。
- (A)成分に対する(C)成分の質量比((C)成分/(A)成分)が、0.5〜10である、請求項1〜10の何れか1項に記載の樹脂組成物。
- さらに(D)エポキシ樹脂を含む、請求項1〜11の何れか1項に記載の樹脂組成物。
- さらに(G)ベンゾシクロブテン樹脂を含む、請求項1〜12の何れか1項に記載の樹脂組成物。
- 樹脂組成物の硬化物(硬化温度200℃)の誘電正接が、5.8GHz、23℃で測定した場合、0.004以下である、請求項1〜13の何れか1項に記載の樹脂組成物。
- 樹脂組成物の硬化物(硬化温度200℃)の比誘電率が、5.8GHz、23℃で測定した場合、3.0以下である、請求項1〜14の何れか1項に記載の樹脂組成物。
- プリント配線板の絶縁層を形成するための請求項1〜15の何れか1項に記載の樹脂組成物。
- 請求項1〜16の何れか1項に記載の樹脂組成物の硬化物。
- 請求項1〜16の何れか1項に記載の樹脂組成物を含有する、シート状積層材料。
- 支持体と、当該支持体上に設けられた請求項1〜16の何れか1項に記載の樹脂組成物から形成される樹脂組成物層と、を有する樹脂シート。
- 請求項1〜16の何れか1項に記載の樹脂組成物の硬化物からなる絶縁層を備えるプリント配線板。
- 請求項20に記載のプリント配線板を含む、半導体装置。
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