JP7409223B2 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JP7409223B2 JP7409223B2 JP2020085486A JP2020085486A JP7409223B2 JP 7409223 B2 JP7409223 B2 JP 7409223B2 JP 2020085486 A JP2020085486 A JP 2020085486A JP 2020085486 A JP2020085486 A JP 2020085486A JP 7409223 B2 JP7409223 B2 JP 7409223B2
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- 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
- RSJKGSCJYJTIGS-BJUDXGSMSA-N undecane Chemical group CCCCCCCCCC[11CH3] RSJKGSCJYJTIGS-BJUDXGSMSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc 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
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
Classifications
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- 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
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- 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
- C08L79/085—Unsaturated polyimide precursors
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- 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
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B27/00—Layered products comprising a layer of synthetic resin
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- B32B27/00—Layered products comprising a layer of synthetic resin
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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
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/06—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the heating method
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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
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/10—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the pressing technique, e.g. using action of vacuum or fluid pressure
- B32B37/1018—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the pressing technique, e.g. using action of vacuum or fluid pressure using only vacuum
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- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- 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
- C08G73/12—Unsaturated polyimide precursors
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- 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
- 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
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- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
- B32B2307/206—Insulating
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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
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Reinforced Plastic Materials (AREA)
Description
[1] (A)橋かけ環骨格を含有するマレイミド化合物、及び(B)活性エステル化合物を含む樹脂組成物。
[2] (A)成分における橋かけ環が、三環系の橋かけ環である、上記[1]に記載の樹脂組成物。
[3] 三環系の橋かけ環が、トリシクロ[5.2.1.02,6]デカン環である、上記[2]に記載の樹脂組成物。
[4] (A)成分1分子中におけるマレイミド基の数が、2である、上記[1]~[3]の何れかに記載の樹脂組成物。
[5] (A)成分が、橋かけ環骨格を含有するマレイミド末端ポリイミドである、上記[1]~[4]の何れかに記載の樹脂組成物。
[6] (A)成分が、さらに芳香族テトラカルボン酸ジイミド骨格を含有する、上記[1]~[5]の何れかに記載の樹脂組成物。
[7] (A)成分が、さらに単環式の非芳香環骨格を含有する、上記[1]~[6]の何れかに記載の樹脂組成物。
[8] (A)成分が、式(A1):
で表されるビスマレイミド化合物である、上記[1]~[7]の何れかに記載の樹脂組成物。
[9] (A)成分の重量平均分子量が、2000~50000である、上記[1]~[8]の何れかに記載の樹脂組成物。
[10] (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、3質量%~30質量%である、上記[1]~[9]の何れかに記載の樹脂組成物。
[11] さらに(A)成分以外の(A’)ラジカル重合性化合物を含む、上記[1]~[10]の何れかに記載の樹脂組成物。
[12] (A)成分の含有量が、樹脂組成物中の全ラジカル重合性化合物を100質量%とした場合、50質量%以上である、上記[1]~[11]の何れかに記載の樹脂組成物。
[13] (B)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、3質量%~30質量%である、上記[1]~[12]の何れかに記載の樹脂組成物。
[14] (B)成分に対する(A)成分の質量比((A)成分/(B)成分)が、0.5~3である、上記[1]~[13]の何れかに記載の樹脂組成物。
[15] さらに(C)エポキシ樹脂を含む、上記[1]~[14]の何れかに記載の樹脂組成物。
[16] さらに(D)無機充填材を含む、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)橋かけ環骨格を含有するマレイミド化合物、及び(B)活性エステル化合物を含む。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、ガラス転移点(Tg)が高く、且つ銅密着性に優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)橋かけ環骨格を含有するマレイミド化合物を含む。(A)橋かけ環骨格を含有するマレイミド化合物とは、分子中に、少なくとも1個の橋かけ環骨格、及び少なくとも1個のマレイミド基(2,5-ジヒドロ-2,5-ジオキソ-1H-ピロール-1-イル基)を含有する有機化合物である。(A)橋かけ環骨格を含有するマレイミド化合物は、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。
本発明の樹脂組成物は、さらに任意成分として(A)成分以外の(A’)ラジカル重合性化合物を含む場合がある。(A’)ラジカル重合性化合物は、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。
(A’-1)マレイミド系ラジカル重合性化合物は、(A)成分以外の化合物であって、1分子中に、1個以上(好ましくは2個以上)のマレイミド基を含有する有機化合物である。(A’-1)マレイミド系ラジカル重合性化合物は、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。(A’-1)マレイミド系ラジカル重合性化合物は、例えば、(A)成分以外の(A’-1-1)マレイミド末端ポリイミド、(A’-1-2)芳香族マレイミド化合物、及び(A’-1-3)脂肪族マレイミド化合物から選ばれる少なくとも1種のマレイミド化合物を含むことが好ましい。
(A’-1-1)マレイミド末端ポリイミドは、橋かけ環骨格を含有しない両末端にマレイミド基を有する鎖状ポリイミドである。(A’-1-1)マレイミド末端ポリイミドは、例えば、ジアミン化合物とマレイン酸無水物とテトラカルボン酸二無水物とを含む成分をイミド化反応させることにより得ることができる成分であり得る。
(A’-1-2)芳香族マレイミド化合物は、(A)及び(A’-1-1)成分には該当しないマレイミド化合物であって、1分子中に、1個以上の芳香環を含み且つ2個以上のマレイミド基を含有するマレイミド化合物を意味する。一実施形態において、(A’-1-2)芳香族マレイミド化合物は、付加重合型の芳香族マレイミドであり得る。(A’-1-2)芳香族マレイミド化合物は、N,N’-1,3-フェニレンジマレイミド、N,N’-1,4-フェニレンジマレイミド等の1個の芳香環を有するマレイミド化合物であってもよいし、2個以上の芳香環を有するマレイミド化合物でもよいが、2個以上の芳香環を有するマレイミド化合物であることが好ましい。
(A’-1-3)脂肪族マレイミド化合物とは、非芳香族炭化水素(好ましくは炭素原子数2~50)を基本骨格とし且つ1分子中に2個以上(好ましくは2個)のマレイミド基を有する化合物である。
(A’-2)ビニルフェニル系ラジカル重合性化合物は、ビニルフェニル基を有するラジカル重合性化合物である。ビニルフェニル系ラジカル重合性化合物は、1分子あたり2個以上のビニルフェニル基を有することが好ましい。
で表される繰り返し単位(繰り返し単位数は好ましくは2~300、より好ましくは2~100)及びビニルベンジル基を有するビニルベンジル変性ポリフェニレンエーテル(特にポリフェニレンエーテルの両末端水酸基の水素原子をビニルベンジル基に置き換えた両末端ビニルベンジル変性ポリフェニレンエーテル)であることが特に好ましい。
で表される繰り返し単位(繰り返し単位数は好ましくは2~200)を有するジビニルベンゼン重合体であることが好ましい。当該ジビニルベンゼン重合体は、さらに、スチレン単位、エチルスチレン単位等のその他のスチレン骨格単位を有する共重合体であってもよい。その他のスチレン骨格単位を有する場合、式(E-2)の繰り返し単位の割合は、全スチレン骨格単位に対して5~70モル%であることが好ましい。
(A’-3)(メタ)アクリル系ラジカル重合性化合物は、アクリロイル基及び/又はメタクリロイル基を有するラジカル重合性化合物である。(A’-3)(メタ)アクリル系ラジカル重合性化合物は、1分子あたり2個以上のアクリロイル基及び/又はメタクリロイル基を有することが好ましい。(A’-3)(メタ)アクリル系ラジカル重合性化合物は、アクリロイル基及び/又はメタクリロイル基並びにポリフェニレンエーテル骨格を有する(メタ)アクリル変性ポリフェニレンエーテルが好ましく、式(F):
で表される繰り返し単位(繰り返し単位数は好ましくは2~300、より好ましくは2~100)並びにアクリロイル基及び/又はメタクリロイル基を有する(メタ)アクリル変性ポリフェニレンエーテル(特にポリフェニレンエーテルの両末端水酸基の水素原子をアクリロイル基及び/又はメタクリロイル基に置き換えた両末端(メタ)アクリル変性ポリフェニレンエーテル)であることが特に好ましい。
本発明の樹脂組成物は、(B)活性エステル化合物を含有する。(B)活性エステル化合物は、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。一実施形態において、樹脂組成物に(C)エポキシ樹脂が含まれる場合、或いは樹脂組成物を(C)エポキシ樹脂と混合する場合、(B)活性エステル化合物は、(C)エポキシ樹脂と反応して(C)エポキシ樹脂を架橋させる機能を有し得る。
本発明の樹脂組成物は、任意成分として(C)エポキシ樹脂を含む場合がある。(C)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、任意成分として(D)無機充填材を含む場合がある。(D)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(E)硬化促進剤を含む場合がある。
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、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;フェノール系硬化剤、ナフトール系硬化剤、酸無水物系硬化剤、チオール系硬化剤、ベンゾオキサジン系硬化剤、シアネートエステル系硬化剤、カルボジイミド系硬化剤、イミダゾール系硬化剤等の活性エステル化合物以外のエポキシ硬化剤;フェノキシ樹脂、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;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。(F)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。(F)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。(G)有機溶剤としては、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。(G)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テート、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。(G)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。
本発明の樹脂組成物は、例えば、任意の調製容器に(A)橋かけ環骨格を含有するマレイミド化合物、(B)活性エステル化合物、必要に応じて(A’)その他のラジカル重合性化合物、必要に応じて(C)エポキシ樹脂、必要に応じて(D)無機充填材、必要に応じて(E)硬化促進剤、必要に応じて(F)その他の添加剤、及び必要に応じて(G)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)橋かけ環骨格を含有するマレイミド化合物、及び(B)活性エステル化合物を含む。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、ガラス転移点(Tg)が高く、且つ銅密着性に優れた硬化物を得ることができる。
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。
橋かけ環骨格含有マレイミド化合物(デザイナーモレキュールズ社製「BMI-2500」)10部、活性エステル化合物(DIC社製「HPC-8150-60T」、固形分60質量%のトルエン溶液)18.3部、ナフトールアラルキル型エポキシ樹脂(日鉄ケミカル&マテリアル社製「ESN-475V」)18部、シランカップリング剤(信越化学工業社製「KBM-573」)で表面処理された球形シリカ(アドマテックス社製「SO-C2」、平均粒径0.5μm、比表面積5.8m2/g)60部、イミダゾール系硬化促進剤(四国化成工業社製「1B2PZ」、1-ベンジル-2-フェニルイミダゾール)1部を混合し、高速回転ミキサーで均一に分散して、樹脂組成物を調製した。
活性エステル化合物(DIC社製「HPC-8150-60T」、固形分60質量%のトルエン溶液)の使用量を18.3部から16.7部に変更し、ナフトールアラルキル型エポキシ樹脂(日鉄ケミカル&マテリアル社製「ESN-475V」)の使用量を18部から15部に変更し、ビフェニルアラルキルノボラック型ポリマレイミド(日本化薬社製「MIR-3000-70MT」、固形分70%のMEK/トルエン混合溶液)5.7部をさらに使用した以外は、実施例1と同様にして、樹脂組成物を調製した。
発明協会公開技報公技番号2020-500211号の合成例1に記載の方法で合成された下記式(1)で表されるマレイミド化合物A(Mw/Mn=1.81、t’’=1.47(主に1、2又は3))のMEK溶液(不揮発成分70質量%)を準備した。
活性エステル化合物(DIC社製「HPC-8150-60T」、固形分60質量%のトルエン溶液)の使用量を18.3部から16.7部に変更し、ナフトールアラルキル型エポキシ樹脂(日鉄ケミカル&マテリアル社製「ESN-475V」)の使用量を18部から15部に変更し、末端ビニルベンジル化PPE化合物(三菱瓦斯化学社製「OPE-2St-2200」、固形分65%のトルエン混合溶液)6.2部をさらに使用した以外は、実施例1と同様にして、樹脂組成物を調製した。
活性エステル化合物(DIC社製「HPC-8150-60T」、固形分60質量%のトルエン溶液)の使用量を18.3部から16.7部に変更し、ナフトールアラルキル型エポキシ樹脂(日鉄ケミカル&マテリアル社製「ESN-475V」)の使用量を18部から15部に変更し、末端メタクリル変性PPE化合物(サビックイノベーティブプラスチックス社製「SA9000-111」、トルエンにて固形分50%溶液に調整)8部をさらに使用した以外は、実施例1と同様にして、樹脂組成物を調製した。
活性エステル化合物(DIC社製「HPC-8150-60T」、固形分60質量%のトルエン溶液)の使用量を18.3部から16.7部に変更し、ナフトールアラルキル型エポキシ樹脂(日鉄ケミカル&マテリアル社製「ESN-475V」)の使用量を18部から15部に変更し、ジビニルベンゼン/スチレン共重合体(日鉄ケミカル&マテリアル社製「ODV-XET-X04」、固形分65%のMEK/トルエン混合溶液)6.2部をさらに使用した以外は、実施例1と同様にして、樹脂組成物を調製した。
橋かけ環骨格含有マレイミド化合物(デザイナーモレキュールズ社製「BMI-2500」)10部の代わりに、脂肪族マレイミド(デザイナーモレキュールズ社製「BMI-689」)10部を使用した以外は、実施例1と同様にして、樹脂組成物を調製した。
橋かけ環骨格含有マレイミド化合物(デザイナーモレキュールズ社製「BMI-2500」)10部の代わりに、ビフェニルアラルキルノボラック型ポリマレイミド(日本化薬社製「MIR-3000-70MT」、固形分70%のMEK/トルエン混合溶液)14.3部を使用した以外は、実施例1と同様にして、樹脂組成物を調製した。
橋かけ環骨格含有マレイミド化合物(デザイナーモレキュールズ社製「BMI-2500」)10部を使用せず、活性エステル化合物(DIC社製「HPC-8150-60T」、固形分60質量%のトルエン溶液)の使用量を18.3部から26.7部に変更し、ナフトールアラルキル型エポキシ樹脂(日鉄ケミカル&マテリアル社製「ESN-475V」)の使用量を18部から23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。
活性エステル化合物(DIC社製「HPC-8150-60T」、固形分60質量%のトルエン溶液)18.3部を使用せず、シランカップリング剤(信越化学工業社製「KBM-573」)で表面処理された球形シリカ(アドマテックス社製「SO-C2」)の使用量を60部から51部に変更し、フェノール系エポキシ硬化剤(DIC社製「LA-7054」、固形分60%のMEK溶液)8.3部をさらに使用した以外は、実施例1と同様にして、樹脂組成物を調製した。
支持体として、離型層を備えたポリエチレンテレフタレートフィルム(リンテック社製「AL5」、厚さ38μm)を用意した。この支持体の離型層上に、実施例及び比較例で得られた樹脂組成物を、乾燥後の樹脂組成物層の厚さが40μmとなるように均一に塗布した。その後、樹脂組成物を80℃~100℃(平均90℃)で4分間乾燥させて、支持体及び樹脂組成物層を含む樹脂シートAを得た。
試験例1で得た樹脂シートAを190℃のオーブンで90分硬化し、更に支持体から剥がすことで硬化フィルムを得た。この硬化フィルムを長さ20mm、幅6mmに切り出し評価サンプルとした。この評価サンプルについてリガク社製TMA装置を用い25℃から250℃まで5℃/分の昇温速度でガラス転移温度(Tg)を測定した。同一の試験片について2回測定を行い、2回目の値を記録した。
(1)内層基板の用意
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。
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、試験例1で得た樹脂シートAを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。
その後、樹脂シートAがラミネートされた内層基板を、130℃のオーブンに投入して30分間加熱し、次いで170℃のオーブンに移し替えて30分間加熱して、樹脂組成物層を熱硬化させて、絶縁層を形成した。その後、支持体を剥離して、絶縁層、内層基板及び絶縁層をこの順に有する硬化基板Aを得た。
硬化基板Aに、粗化処理としてのデスミア処理を行った。デスミア処理としては、下記の湿式デスミア処理を実施した。
硬化基板Aを、膨潤液(アトテックジャパン社製「スウェリング・ディップ・セキュリガントP」、ジエチレングリコールモノブチルエーテル及び水酸化ナトリウムの水溶液)に60℃で5分間浸漬し、次いで、酸化剤溶液(アトテックジャパン社製「コンセントレート・コンパクトCP」、過マンガン酸カリウム濃度約6%、水酸化ナトリウム濃度約4%の水溶液)に80℃で20分間浸漬した。次いで、中和液(アトテックジャパン社製「リダクションソリューション・セキュリガントP」、硫酸水溶液)に40℃で5分間浸漬した後、80℃で15分間乾燥した。
粗化処理後の硬化基板Aの絶縁層表面の算術平均粗さ(Ra)を、非接触型表面粗さ計(ブルカー社製WYKO NT3300)を用いて、VSIモード、50倍レンズにより測定範囲を121μm×92μmとして得られる数値により求めた。それぞれ10点の平均値を求めることにより測定した。
(1)銅めっき導体層の形成
セミアディティブ法に従って、試験例3で得られた粗化処理後の硬化基板Aの絶縁層の粗化面に導体層を形成した。すなわち、粗化処理後の基板を、PdCl2を含む無電解めっき液に40℃で5分間浸漬した後、無電解銅めっき液に25℃で20分間浸漬した。次いで、150℃にて30分間加熱してアニール処理を行った後に、エッチングレジストを形成し、エッチングによりパターン形成した。その後、硫酸銅電解めっきを行い、厚さ25μmの導体層を形成し、アニール処理を190℃にて60分間行った。得られた基板を「評価基板B」と称する。
絶縁層と導体層のピール強度の測定は、日本工業規格(JIS C6481)に準拠して行った。具体的には、評価基板Bの導体層に、幅10mm、長さ100mmの部分の切込みをいれ、こ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。
(1)銅箔の下地処理
三井金属鉱業(株)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(株)製「CZ8101」)に浸漬して銅表面に粗化処理(Ra値=1μm)を行い、防錆処理(CL8300)を施した。この銅箔をCZ銅箔という。さらに、130℃のオーブンで30分間加熱処理した。
試験例1と同様の方法で樹脂シートAがラミネートされた内層基板を用意した。その後、当該基板から、両面にある支持体を剥離し、双方の樹脂組成物層を露出させた。それらの樹脂組成物層上に、「3EC-III」のCZ銅箔の処理面を、試験例1の樹脂シートAのラミネートと同様の条件で、積層した。そして、190℃、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、サンプルを作製した。
作製したサンプルを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((株)TSE製「AC-50C-SL」)で掴み、インストロン万能試験機を用いて、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(N/cm)]をJIS C6481に準拠して測定した。
Claims (16)
- (A)橋かけ環骨格を含有するマレイミド化合物、(B)活性エステル化合物、(C)エポキシ樹脂、(D)無機充填材、並びに(A’-2)ビニルフェニル系ラジカル重合性化合物及び/又は(A’-3)(メタ)アクリル系ラジカル重合性化合物を含み、
(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、5質量%~30質量%であり、
(B)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、5質量%~30質量%であり、
(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、5質量%~30質量%であり、
(D)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%~80質量%であり、
(A’-2)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、0質量%~10質量%であり、
(A’-3)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、0質量%~10質量%である樹脂組成物。 - (A)成分における橋かけ環が、三環系の橋かけ環である、請求項1に記載の樹脂組成物。
- 三環系の橋かけ環が、トリシクロ[5.2.1.02,6]デカン環である、請求項2に記載の樹脂組成物。
- (A)成分1分子中におけるマレイミド基の数が、2である、請求項1~3の何れか1項に記載の樹脂組成物。
- (A)成分が、橋かけ環骨格を含有するマレイミド末端ポリイミドである、請求項1~4の何れか1項に記載の樹脂組成物。
- (A)成分が、さらに芳香族テトラカルボン酸ジイミド骨格を含有する、請求項1~5の何れか1項に記載の樹脂組成物。
- (A)成分が、さらに単環式の非芳香環骨格を含有する、請求項1~6の何れか1項に記載の樹脂組成物。
- (A)成分が、式(A1):
で表されるビスマレイミド化合物である、請求項1~7の何れか1項に記載の樹脂組成物。 - (A)成分の重量平均分子量が、2000~50000である、請求項1~8の何れか1項に記載の樹脂組成物。
- (A)成分の含有量が、樹脂組成物中の全ラジカル重合性化合物を100質量%とした場合、50質量%以上である、請求項1~9の何れか1項に記載の樹脂組成物。
- (B)成分に対する(A)成分の質量比((A)成分/(B)成分)が、0.5~3である、請求項1~10の何れか1項に記載の樹脂組成物。
- 請求項1~11の何れか1項に記載の樹脂組成物の硬化物。
- 請求項1~11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1~11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1~11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15に記載のプリント配線板を含む、半導体装置。
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