JP7107218B2 - 樹脂組成物、樹脂層付き支持体、プリプレグ、積層板、多層プリント配線板及びミリ波レーダー用プリント配線板 - Google Patents
樹脂組成物、樹脂層付き支持体、プリプレグ、積層板、多層プリント配線板及びミリ波レーダー用プリント配線板 Download PDFInfo
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- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
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- C08K5/372—Sulfides, e.g. R-(S)x-R'
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- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
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- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
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- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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- C08L35/00—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 a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; 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
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- H05K1/02—Details
- H05K1/0213—Electrical arrangements not otherwise provided for
- H05K1/0237—High frequency adaptations
- H05K1/024—Dielectric details, e.g. changing the dielectric material around a transmission line
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
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- C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
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Description
本明細書において、高周波領域とは、0.3GHz~300GHzを指し、特にミリ波レーダーに用いられる周波数領域は3GHz~300GHzを指すものとする。本明細書において、「~」を用いて示された数値範囲は、「~」の前後に記載されている数値をそれぞれ最小値及び最大値として含む範囲を示す。本明細書には段階的に記載されている数値範囲において、ある段階の数値範囲の上限値又は下限値は、他の段階の数値範囲の上限値又は下限値に置き換えてもよい。本明細書に記載されている数値範囲において、その数値範囲の上限値又は下限値は、実施例に示されている値に置き換えてもよい。「A又はB」とは、A及びBのどちらか一方を含んでいればよく、両方とも含んでいてもよい。本明細書において、組成物中の各成分の含有量は、組成物中に各成分に該当する物質が複数存在する場合、特に断らない限り、組成物中に存在する複数の物質の合計量を意味する。
本実施形態の樹脂組成物は、(A)マレイミド基、少なくとも2つのイミド結合を有する2価の基及び飽和又は不飽和の2価の炭化水素基を有する化合物と、(B)非ハロゲン系難燃剤と、を含有する。
本実施形態に係る(a)マレイミド基、(b)少なくとも2つのイミド結合を有する2価の基及び(c)飽和又は不飽和の2価の炭化水素基を有する化合物を(A)成分ということがある。また、(a)マレイミド基を構造(a)、(b)少なくとも2つのイミド結合を有する2価の基を構造(b)、(c)飽和又は不飽和の2価の炭化水素基を構造(c)ということがある。(A)成分を用いることで、高周波特性及び導体との高い接着性を有する樹脂組成物を得ることができる。
ポンプ:L-6200型[株式会社日立ハイテクノロジーズ製]
検出器:L-3300型RI[株式会社日立ハイテクノロジーズ製]
カラムオーブン:L-655A-52[株式会社日立ハイテクノロジーズ製]
ガードカラム及びカラム:TSK Guardcolumn HHR-L+TSKgel G4000HHR+TSKgel G2000HHR[すべて東ソー株式会社製、商品名]
カラムサイズ:6.0×40mm(ガードカラム)、7.8×300mm(カラム)
溶離液:テトラヒドロフラン
試料濃度:30mg/5mL
注入量:20μL
流量:1.00mL/分
測定温度:40℃
本実施形態の樹脂組成物は、(A)成分とは異なるマレイミド基含有化合物を更に含有することができる。該マレイミド基含有化合物を(A2)成分ということがある。なお、(A)成分及び(A2)成分の双方に該当し得る化合物は、(A)成分に帰属するものとする。(A2)成分を用いることで、樹脂組成物は、特に低熱膨張特性に優れるものとなる。すなわち、本実施形態の樹脂組成物は、(A)成分と(A2)成分を併用することにより、良好な誘電特性を維持しつつ、低熱膨張特性等を更に向上させることができる。この理由として、(A)成分と(A2)成分とを含有する樹脂組成物から得られる硬化物は、低誘電特性を備える(A)成分からなる構造単位と、低熱膨張である(A2)成分からなる構造単位とを備えるポリマーを含有するためだと推測される。
本実施形態に係る樹脂組成物には、ジアミン化合物を更に含有してもよい。ジアミン化合物は特に限定されないが、例えば、4,4’-ジアミノジフェニルメタン、4,4’-ジアミノ-3,3’-ジメチル-ジフェニルメタン、2,2’-ジメチル-4,4’-ジアミノビフェニル、2,2-ビス(4-(4-アミノフェノキシ)フェニル)プロパン、4,4’-[1,3-フェニレンビス(1-メチルエチリデン)]ビスアニリン、4,4’-[1,4-フェニレンビス(1-メチルエチリデン)]ビスアニリン、1,3-ビス[2-(4-アミノフェニル)-2-プロピル]ベンゼン等が挙げられる。これらは1種類を単独で用いても、2種類以上を併用してもよい。
本実施形態の樹脂組成物は、(A)成分の硬化を促進するための触媒を更に含有してもよい。触媒の含有量は特に限定されないが、樹脂組成物の全質量に対して0.1~5質量%であってもよい。触媒としては、例えば、過酸化物、アゾ化合物等を用いることができる。
本実施形態に係る(B)非ハロゲン系難燃剤を(B)成分ということがある。(B)成分を用いることで、高周波特性の大幅な悪化がなく導体との高い接着性を有し、かつ、難燃性を有する樹脂組成物を得ることができる。さらに、環境負荷を低減することができる。
本実施形態の樹脂組成物は、(A)成分及び(A2)成分とは異なる熱硬化性樹脂を更に含有することができる。なお、(A)成分又は(A2)成分に該当し得る化合物は、(C)熱硬化性樹脂に帰属しないものとする。(C)熱硬化性樹脂としては、例えば、エポキシ樹脂、シアネートエステル樹脂等が挙げられる。(C)熱硬化性樹脂を含むことで、樹脂組成物の低熱膨張特性等を更に向上させることができる。
本実施形態の樹脂組成物は、(C)熱硬化性樹脂の硬化剤を更に含有してもよい。これにより、樹脂組成物の硬化物を得る際の反応を円滑に進めることができるとともに、得られる樹脂組成物の硬化物の物性を適度に調節することが可能となる。
本実施形態の樹脂組成物には、(C)熱硬化性樹脂の種類に応じて硬化促進剤を更に配合してもよい。エポキシ樹脂の硬化促進剤としては、例えば、潜在性の熱硬化剤である各種イミダゾール類、BF3アミン錯体、リン系硬化促進剤等が挙げられる。硬化促進剤を配合する場合、樹脂組成物の保存安定性、半硬化の樹脂組成物の取扱性及びはんだ耐熱性の観点から、イミダゾール類及びリン系硬化促進剤が好ましい。
本実施形態の樹脂組成物は、無機充填剤を更に含有してもよい。任意に適切な無機充填剤を含有させることで、樹脂組成物の低熱膨張特性、高弾性率性、耐熱性、難燃性等を向上させることができる。無機充填剤としては特に制限されないが、例えば、シリカ、アルミナ、酸化チタン、マイカ、ベリリア、チタン酸バリウム、チタン酸カリウム、チタン酸ストロンチウム、チタン酸カルシウム、炭酸アルミニウム、水酸化マグネシウム、水酸化アルミニウム、ケイ酸アルミニウム、炭酸カルシウム、ケイ酸カルシウム、ケイ酸マグネシウム、窒化ケイ素、窒化ホウ素、焼成クレー、タルク、ホウ酸アルミニウム、炭化ケイ素等が挙げられる。これらは1種類を単独で用いても、2種類以上を併用してもよい。
本実施形態の樹脂組成物は、樹脂フィルムの取扱性を高める観点から、熱可塑性樹脂を更に含有してもよい。熱可塑性樹脂の種類は特に限定されず、分子量も限定されないが、(A)成分との相溶性をより高める点から、数平均分子量(Mn)が200~60000であることが好ましい。
本実施形態の樹脂組成物には、本発明の効果を損なわない範囲で、上記(B)成分以外の難燃剤を更に配合してもよい。難燃剤としては特に限定されないが、臭素系難燃剤が好適に用いられる。臭素系難燃剤としては、臭素化ビスフェノールA型エポキシ樹脂、臭素化フェノールノボラック型エポキシ樹脂等の臭素化エポキシ樹脂;ヘキサブロモベンゼン、ペンタブロモトルエン、エチレンビス(ペンタブロモフェニル)、エチレンビステトラブロモフタルイミド、1,2-ジブロモ-4-(1,2-ジブロモエチル)シクロヘキサン、テトラブロモシクロオクタン、ヘキサブロモシクロドデカン、ビス(トリブロモフェノキシ)エタン、臭素化ポリフェニレンエーテル、臭素化ポリスチレン、2,4,6-トリス(トリブロモフェノキシ)-1,3,5-トリアジン等の臭素化添加型難燃剤;トリブロモフェニルマレイミド、トリブロモフェニルアクリレート、トリブロモフェニルメタクリレート、テトラブロモビスフェノールA型ジメタクリレート、ペンタブロモベンジルアクリレート、臭素化スチレン等の不飽和二重結合基含有の臭素化反応型難燃剤などが挙げられる。これらの難燃剤は1種類を単独で用いてもよく、2種類以上を組み合わせて用いてもよい。
本実施形態では、上記の樹脂組成物を用いて、樹脂フィルムを製造することができる。なお、樹脂フィルムとは未硬化又は半硬化のフィルム状の樹脂組成物を指す。
本実施形態のプリプレグは、上述の樹脂組成物と、繊維基材とから構成される。
本実施形態によれば、上述の樹脂組成物の硬化物を含む樹脂層と、導体層と、を有する積層板を提供することができる。例えば、上記樹脂フィルム、樹脂層付き支持体又はプリプレグを用い、金属張積層板を製造することができる。
本実施形態によれば、上述の樹脂組成物の硬化物を含む樹脂層と、少なくとも3層の回路層とを備える、多層プリント配線板を提供することができる。回路層の数の上限値は特に限定されず、3層~20層であってもよい。多層プリント配線板は、例えば、上記の樹脂フィルム、樹脂層付き支持体、プリプレグ又は金属張積層板を用いて製造することもできる。
下記手順に従って、各種の樹脂組成物を調製した。実施例1~19及び比較例1~2の樹脂組成物の調製に用いた各原材料の使用量(質量部)は、表1、表2及び表3にまとめて示す。
(1)BMI-3000[Mw:約3000、Designer Molecules Inc.製、商品名]
(2)BMI-5000[Mw:約5000、Designer Molecules Inc.製、商品名]
(3)BMI-1000[ビス(4-マレイミドフェニル)メタン、大和化成工業株式会社製、商品名]
(4)BMI-4000[2,2-ビス(4-(4-マレイミドフェノキシ)フェニル)プロパン、大和化成工業株式会社製、商品名]
(5)ビスアニリンM[1,3-ビス(2-(4-アミノフェニル)-2-プロピル)ベンゼン、三井化学ファインケミカル株式会社製、商品名]
(6)シリカスラリー[球状溶融シリカ、株式会社アドマテックス製]
(7)AO-20[1,3,5-トリス(3’,5’-ジ-t-ブチル-4’-ヒドロキシベンジル)-sec-トリアジン-2,4,6-(1H,3H、5H)トリオン、株式会社ADEKA製、商品名]
(8)AO-30[1,1,3-トリス(2-メチル-4-ヒドロキシ-5-t-ブチルフェニル)ブタン、株式会社ADEKA製、商品名]
(9)AO-330[1,3,5-トリメチル-2,4,6-トリス(3,5-ジ-t-ブチル-4-ヒドロキシベンジル)ベンゼン、株式会社ADEKA製、商品名]
(10)PEP-8[サイクリックネオペンタンテトライルビス(オクタデシルホスファイト)、株式会社ADEKA製、商品名]
(11)PEP-36[サイクリックネオペンタンテトライルビス(2,6-ジ-t-ブチル-4-メチルフェニル)ホスファイト、株式会社ADEKA製、商品名]
(12)スミライザーTPL[ジラウリル3,3’-チオジプロピオネート、住友化学株式会社製、商品名]
(13)OP-935[ジアルキルホスフィン酸アルミニウム塩、2置換ホスフィン酸の金属塩、リン含有量:23.5質量%、クラリアント社製、商品名]
(14)PX-200[1,3-フェニレンビス(ジ-2,6-キシレニルホスフェート)、芳香族リン酸エステル、リン含有量:9質量%、大八化学工業株式会社製、商品名]
(15)HCA-HQ[10-(2,5-ジヒドロキシフェニル)-9,10-ジヒドロ-9-オキサ-10-ホスファフェナントレン-10-オキシド、環状有機リン化合物、リン含有量:9.6質量%、三光株式会社製、商品名]
(16)KMP-605[球状シリコーンパウダー、信越シリコーン株式会社製、商品名]
(17)AlOOH[ベーマイト型水酸化アルミニウム、金属水和物、密度3.0g/cm3、河合石灰工業株式会社製、商品名]
(18)パーブチルP[α,α’-ジ(ターシャリーブチルパーオキシ)ジイソプロピルベンゼン、日油株式会社製、商品名]
実施例及び比較例の半硬化樹脂フィルムの外観及び取扱性を評価した。結果を表4、表5及び表6に示す。
○:半硬化樹脂フィルムの表面にムラ、スジ等がない。
×:半硬化樹脂フィルムの表面に実施不可能な状態でムラ、スジ等があり、表面平滑性に欠ける。
(1)25℃における表面のべたつき(タック)の有無。
(2)カッターナイフで切断した際の状態の樹脂割れ又は粉落ちの有無。
○:上記(1)及び(2)のいずれも無い。
×:上記(1)及び(2)のいずれか一方でも有る。
上述の樹脂層付き支持体からPETフィルムを剥離した樹脂フィルムを2枚重ねた後、その両面に、厚さ18μmのロープロファイル銅箔(M面Rz:3μm、古河電気工業株式会社製、商品名「F3-WS」)をその粗化面(M面)が接するように配置し、その上に鏡板を乗せ、200℃/3.0MPa/70分のプレス条件で加熱及び加圧成形して、両面金属張硬化樹脂フィルム(厚さ:0.1mm)を作製した。
耐折曲げ性は、両面金属張硬化樹脂フィルムの外層銅箔をエッチングしたものを180度折り曲げることにより、下記基準により評価した。
○:折り曲げた際、割れ又はクラックが発生しない。
×:折り曲げた際、割れ又はクラックが実施不可能な状態で発生する。
誘電特性である比誘電率及び誘電正接は、両面金属張硬化樹脂フィルムの外層銅箔をエッチングし、長さ60mm、幅2mm、厚み約1mmに切断したものを試験片として空洞共振器摂動法により測定した。測定器にはアジレントテクノロジー社製ベクトル型ネットワークアナライザE8364B、空洞共振器には株式会社関東電子応用開発製CP129(10GHz帯共振器)及びCP137(20GHz帯共振器)、測定プログラムにはCPMA-V2をそれぞれ使用した。条件は、周波数10GHz、測定温度25℃とした。
銅箔引きはがし強さは、銅張積層板試験規格JIS-C-6481に準拠して測定した。測定温度は25℃とした。
はんだ耐熱性は、両面金属張硬化樹脂フィルムの片側の銅箔をエッチングし、50mm角に切断したものを試験片として、その常態及びプレッシャークッカーテスト(PCT)装置(条件:121℃、2.2気圧)において、所定時間(1、3、5時間)処理した後のものを288℃の溶融はんだ上に20秒間フロートし、処理時間が異なる3枚の硬化樹脂フィルムのそれぞれの外観を下記基準により目視で評価した。なお、表4、表5及び表6においては、1時間の処理を行ったものをPCT-1hと表記し、3時間の処理を行ったものをPCT-3hと表記し、5時間の処理を行ったものをPCT-5hと表記する。また、表中の「○(3/3)」との表記は、同時間の処理を行った三枚の試験片のうち三枚とも下記評価基準において○であったことを示す。
○:フィルム内部及びフィルムと銅箔間に膨れ又はミーズリングの発生が認められない。
×:フィルム内部及びフィルムと銅箔間に膨れ又はミーズリングの発生が見られる。
熱膨張係数(板厚方向)は、両面金属張硬化樹脂フィルムの両面の銅箔をエッチングし、5mm角に切断したものを試験片として、熱機械分析装置TMA(TAインスツルメント社製、Q400)(温度範囲:30~150℃、荷重:5g)により、IPC規格(IPC-TM-650 2.4.24)に準拠して測定した。
難燃性は、UL-94垂直試験法に準拠して評価した。なお、表6において、比較例1の難燃性評価結果の「×」との表記は、UL-94垂直試験法に準拠して評価した結果、V-2の評価基準を満たさなかったことを示す。
Claims (48)
- 前記(B)非ハロゲン系難燃剤がフェノール系酸化防止剤を含む、請求項1に記載の樹脂組成物。
- 前記(B)非ハロゲン系難燃剤がホスファイト系酸化防止剤を含む、請求項1に記載の樹脂組成物。
- 前記(B)非ハロゲン系難燃剤がチオエーテル系酸化防止剤を含む、請求項1に記載の樹脂組成物。
- 前記(B)非ハロゲン系難燃剤がリン系難燃剤を含む、請求項1に記載の樹脂組成物。
- 前記化合物とは異なるマレイミド基含有化合物を更に含有する、請求項1~6のいずれか一項に記載の樹脂組成物。
- 前記(B)非ハロゲン系難燃剤がフェノール系酸化防止剤を含む、請求項8に記載の樹脂層付き支持体。
- 前記(B)非ハロゲン系難燃剤がホスファイト系酸化防止剤を含む、請求項8に記載の樹脂層付き支持体。
- 前記(B)非ハロゲン系難燃剤がチオエーテル系酸化防止剤を含む、請求項8に記載の樹脂層付き支持体。
- 前記(B)非ハロゲン系難燃剤がリン系難燃剤を含む、請求項8に記載の樹脂層付き支持体。
- 前記樹脂組成物が、前記化合物とは異なるマレイミド基含有化合物を更に含有する、請求項8~13のいずれか一項に記載の樹脂層付き支持体。
- 前記樹脂組成物の硬化物の10GHzでの比誘電率が3.6以下である、請求項8~14のいずれか一項に記載の樹脂層付き支持体。
- 前記(B)非ハロゲン系難燃剤がフェノール系酸化防止剤を含む、請求項16に記載のプリプレグ。
- 前記(B)非ハロゲン系難燃剤がホスファイト系酸化防止剤を含む、請求項16に記載のプリプレグ。
- 前記(B)非ハロゲン系難燃剤がチオエーテル系酸化防止剤を含む、請求項16に記載のプリプレグ。
- 前記(B)非ハロゲン系難燃剤がリン系難燃剤を含む、請求項16に記載のプリプレグ。
- 前記樹脂組成物が、前記化合物とは異なるマレイミド基含有化合物を更に含有する、請求項16~21のいずれか一項に記載のプリプレグ。
- 前記樹脂組成物の硬化物の10GHzでの比誘電率が3.6以下である、請求項16~22のいずれか一項に記載のプリプレグ。
- 前記(B)非ハロゲン系難燃剤がフェノール系酸化防止剤を含む、請求項24に記載の積層板。
- 前記(B)非ハロゲン系難燃剤がホスファイト系酸化防止剤を含む、請求項24に記載の積層板。
- 前記(B)非ハロゲン系難燃剤がチオエーテル系酸化防止剤を含む、請求項24に記載の積層板。
- 前記(B)非ハロゲン系難燃剤がリン系難燃剤を含む、請求項24に記載の積層板。
- 前記樹脂組成物が、前記化合物とは異なるマレイミド基含有化合物を更に含有する、請求項24~29のいずれか一項に記載の積層板。
- 前記樹脂組成物の硬化物の10GHzでの比誘電率が3.6以下である、請求項24~30のいずれか一項に記載の積層板。
- 前記(B)非ハロゲン系難燃剤がフェノール系酸化防止剤を含む、請求項32に記載の多層プリント配線板。
- 前記(B)非ハロゲン系難燃剤がホスファイト系酸化防止剤を含む、請求項32に記載の多層プリント配線板。
- 前記(B)非ハロゲン系難燃剤がチオエーテル系酸化防止剤を含む、請求項32に記載の多層プリント配線板。
- 前記(B)非ハロゲン系難燃剤がリン系難燃剤を含む、請求項32に記載の多層プリント配線板。
- 前記樹脂組成物が、前記化合物とは異なるマレイミド基含有化合物を更に含有する、請求項32~37のいずれか一項に記載の多層プリント配線板。
- 前記樹脂組成物の硬化物の10GHzでの比誘電率が3.6以下である、請求項32~38のいずれか一項に記載の多層プリント配線板。
- 請求項32~39のいずれか一項に記載の多層プリント配線板のミリ波レーダーへの応用。
- 前記(B)非ハロゲン系難燃剤がフェノール系酸化防止剤を含む、請求項41に記載のミリ波レーダー用プリント配線板。
- 前記(B)非ハロゲン系難燃剤がホスファイト系酸化防止剤を含む、請求項41に記載のミリ波レーダー用プリント配線板。
- 前記(B)非ハロゲン系難燃剤がチオエーテル系酸化防止剤を含む、請求項41に記載のミリ波レーダー用プリント配線板。
- 前記(B)非ハロゲン系難燃剤がリン系難燃剤を含む、請求項41に記載のミリ波レーダー用プリント配線板。
- 前記樹脂組成物が、前記化合物とは異なるマレイミド基含有化合物を更に含有する、請求項41~46のいずれか一項に記載のミリ波レーダー用プリント配線板。
- 前記樹脂組成物の硬化物の10GHzでの比誘電率が3.6以下である、請求項41~47のいずれか一項に記載のミリ波レーダー用プリント配線板。
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JP2016040797A (ja) | 2014-08-12 | 2016-03-24 | 日本シイエムケイ株式会社 | 多層プリント配線板 |
WO2017027482A1 (en) | 2015-08-08 | 2017-02-16 | Designer Molecules, Inc. | Anionic curable compositions |
JP2017043767A (ja) | 2015-08-24 | 2017-03-02 | 信越化学工業株式会社 | 熱硬化性樹脂組成物 |
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US20190241717A1 (en) | 2019-08-08 |
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JP2024086772A (ja) | 2024-06-28 |
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CN113337117B (zh) | 2023-07-14 |
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