JP2007169454A5 - - Google Patents
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- JP2007169454A5 JP2007169454A5 JP2005368905A JP2005368905A JP2007169454A5 JP 2007169454 A5 JP2007169454 A5 JP 2007169454A5 JP 2005368905 A JP2005368905 A JP 2005368905A JP 2005368905 A JP2005368905 A JP 2005368905A JP 2007169454 A5 JP2007169454 A5 JP 2007169454A5
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- JP
- Japan
- Prior art keywords
- hydroxyl group
- polybutadiene
- prepreg according
- polyimide resin
- component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 239000005062 Polybutadiene Substances 0.000 claims description 31
- 229920002857 polybutadiene Polymers 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 27
- 229920005989 resin Polymers 0.000 claims description 27
- 229920001721 Polyimide Polymers 0.000 claims description 26
- 239000009719 polyimide resin Substances 0.000 claims description 24
- -1 diisocyanate compound Chemical class 0.000 claims description 21
- 230000001588 bifunctional Effects 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 17
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 14
- 229920001187 thermosetting polymer Polymers 0.000 claims description 13
- 125000006159 dianhydride group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 8
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000011342 resin composition Substances 0.000 claims description 7
- 125000004018 acid anhydride group Chemical group 0.000 claims description 6
- 239000003822 epoxy resin Substances 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 229920000647 polyepoxide Polymers 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 5
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 4
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2H-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004643 cyanate ester Substances 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 230000003014 reinforcing Effects 0.000 claims description 4
- 239000004065 semiconductor Substances 0.000 claims description 4
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 101700080837 HNF1B Proteins 0.000 claims 1
- FLFYVGMUAROSCQ-UHFFFAOYSA-N N-(6-aminohexyl)-2,6-bis[3-(2,5-dioxopyrrol-1-yl)propanoylamino]hexanamide Chemical compound O=C1C=CC(=O)N1CCC(=O)NC(C(=O)NCCCCCCN)CCCCNC(=O)CCN1C(=O)C=CC1=O FLFYVGMUAROSCQ-UHFFFAOYSA-N 0.000 claims 1
- 0 CC(C)(C)*NC(O*OC(NC(C)(C)C)=O)=O Chemical compound CC(C)(C)*NC(O*OC(NC(C)(C)C)=O)=O 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 1
Description
すなわち、本発明は以下の内容を含むものである。
［１］（Ａ）ポリブタジエン構造の含有率が４５質量％以上である、２官能性ヒドロキシル基末端ポリブタジエン、ジイソシアネート化合物及び四塩基酸無水物を反応させて得られる線状変性ポリイミド樹脂、及び（Ｂ）エポキシ樹脂、ビスマレイミド樹脂、シアネートエステル樹脂、ビスアリルナジイミド樹脂、ビニルベンジルエーテル樹脂、ベンゾオキサジン樹脂及びビスマレイミドとジアミンの重合物から選択される１種以上の熱硬化性樹脂を含有する熱硬化性樹脂組成物が繊維からなるシート状補強基材中に含浸されていることを特徴とするプリプレグ。
［２］成分（Ａ）の線状変性ポリイミド樹脂が、２官能性ヒドロキシル基末端ポリブタジエンとジイソシアネート化合物を、２官能性ヒドロキシル基末端ポリブタジエンのヒドロキシル基に対するジイソシアネート化合物のイソシアネート基の官能基当量比が１を超える比率で反応させて得られるポリブタジエンジイソシアネート組成物に、四塩基酸二無水物を反応させて得られる線状変性ポリイミド樹脂である、上記［１］に記載のプリプレグ。
［３］成分（Ａ）の線状変性ポリイミド樹脂が、２官能性ヒドロキシル基末端ポリブタジエンとジイソシアネート化合物を、２官能性ヒドロキシル基末端ポリブタジエンのヒドロキシル基とジイソシアネート化合物のイソシアネート基の官能基当量比が１：１．５〜１：２．５となる比率で反応させて得られるポリブタジエンジイソシアネート組成物に、四塩基酸二無水物を反応させて得られる線状変性ポリイミド樹脂である、上記［１］に記載のプリプレグ。
［４］成分（Ａ）の線状変性ポリイミド樹脂が、２官能性ヒドロキシル基末端ポリブタジエンとジイソシアネート化合物を、２官能性ヒドロキシル基末端ポリブタジエンのヒドロキシル基とジイソシアネート化合物のイソシアネート基の官能基当量比が１：１．５〜１：２．５となる比率で反応させて得られるポリブタジエンジイソシアネート組成物に、四塩基酸二無水物を、原料であるジイソシアネート化合物のイソシアネート基の官能基当量Ｘ、原料である２官能ヒドロキシル末端ポリブタジエンのヒドロキシル基の官能基当量Ｗ及び四塩基酸二無水物の酸無水物基の官能基当量Ｙが、Ｙ＞Ｘ−Ｗ≧Ｙ／５（Ｗ＞０、Ｘ＞０、Ｙ＞０）の関係を満たす比率で反応させて得られる線状変性ポリイミド樹脂である、上記［１］に記載のプリプレグ。
［５］成分（Ａ）の線状変性ポリイミド樹脂が、上記［１］〜［４］のいずれかに記載の線状変性ポリイミド樹脂に、更に新たなイソシアネート化合物を、原料であるジイソシアネート化合物のイソシアネート官能基当量Ｘ、原料である２官能ヒドロキシル末端ポリブタジエンのヒドロキシル基官能基当量Ｗ、四塩基酸二無水物の酸無水物基の官能基当量Ｙ及び新たに反応させるイソシアネート化合物のイソシアネート官能基当量Ｚが、Ｙ−（Ｘ−Ｗ）＞Ｚ≧０（Ｗ＞０、Ｘ＞０、Ｙ＞０、Ｚ＞０）の関係を満たす比率で反応させて得られる線状変性ポリイミド樹脂である、上記［１］〜［４］のいずれかに記載のプリプレグ。
［６］（Ａ）分子内に下式（１−ａ）で表されるポリブタジエン構造及び下式（１−ｂ）で表されるポリイミド構造を有する線状変性ポリイミド樹脂、
及び（Ｂ）エポキシ樹脂、ビスマレイミド樹脂、シアネートエステル樹脂、ビスアリルナジイミド樹脂、ビニルベンジルエーテル樹脂、ベンゾオキサジン樹脂及びビスマレイミドとジアミンの重合物から選択される１種以上の熱硬化性樹脂を含有する熱硬化性樹脂組成物が繊維からなるシート状補強基材中に含浸されていることを特徴とするプリプレグ。
［７］成分（Ａ）の線状変性ポリイミド樹脂中のポリブタジエン構造の含有率が６０質量％以上である、上記［１］〜［６］のいずれかに記載のプリプレグ。
［８］Ｒ１が、数平均分子量８００〜１００００である２官能性ヒドロキシル基末端ポリブタジエンのヒドロキシル基を除いた残基を示す、上記［１］〜［７］のいずれかに記載のプリプレグ。
［９］成分（Ａ）と成分（Ｂ）の配合割合が質量比で１００：１〜１：１であり、熱硬化樹脂組成物中の成分（Ａ）及び成分（Ｂ）の合計含量が７０質量％以上である、上記［１］〜［８］のいずれかに記載のプリプレグ。
［１０］更に充填材を含有する上記［１］〜［９］のいずれかに記載のプリプレグ。
［１１］成分（Ｂ）の熱硬化性樹脂がエポキシ樹脂である上記［１］〜［１０］のいずれかに記載のプリプレグ。
［１２］更にエポキシ硬化剤を含有する上記［１１］記載のプリプレグ。
［１３］シート状繊維基材の厚さが５０μｍ以下であることを特徴とする、上記［１］〜［１２］のいずれかに記載のプリプレグ。
［１４］上記［１］〜［１３］のいずれかに記載のプリプレグの硬化物により絶縁層の一部又は全部が形成されている多層プリント配線板。
［１５］上記［１］〜［１３］のいずれかに記載のプリプレグの硬化物上に回路が形成されているフレキシブル回路基板。
［１６］半導体とサブストレート基板が上記［１］〜［１３］のいずれかに記載の熱硬化性樹脂組成物の硬化物を介して接着されている半導体装置。That is, the present invention includes the following contents.
[1] (A) A linear modified polyimide resin obtained by reacting a bifunctional hydroxyl group-terminated polybutadiene, a diisocyanate compound, and a tetrabasic acid anhydride, having a polybutadiene structure content of 45% by mass or more , and (B ) Heat containing one or more thermosetting resins selected from epoxy resins, bismaleimide resins, cyanate ester resins, bisallyl nadiimide resins, vinyl benzyl ether resins, benzoxazine resins, and polymers of bismaleimides and diamines A prepreg characterized in that a curable resin composition is impregnated in a sheet-like reinforcing base material comprising fibers.
[2] The linear modified polyimide resin of component (A) is a bifunctional hydroxyl group-terminated polybutadiene and diisocyanate compound, and the functional group equivalent ratio of the isocyanate group of the diisocyanate compound to the hydroxyl group of the bifunctional hydroxyl group-terminated polybutadiene is 1. The prepreg according to the above [1], which is a linear modified polyimide resin obtained by reacting a tetrabutadiene dianhydride with a polybutadiene diisocyanate composition obtained by reacting at a ratio exceeding.
[3] The linear modified polyimide resin of component (A) is a bifunctional hydroxyl group-terminated polybutadiene and diisocyanate compound, and the functional group equivalent ratio of the hydroxyl group of the bifunctional hydroxyl group-terminated polybutadiene and the isocyanate group of the diisocyanate compound is 1. : A linear modified polyimide resin obtained by reacting tetrabasic acid dianhydride with a polybutadiene diisocyanate composition obtained by reacting at a ratio of 1.5 to 1: 2.5. The prepreg as described.
[4] The linear modified polyimide resin of component (A) is a bifunctional hydroxyl group-terminated polybutadiene and diisocyanate compound, and the functional group equivalent ratio of the hydroxyl group of the bifunctional hydroxyl group-terminated polybutadiene and the isocyanate group of the diisocyanate compound is 1. : Polybutadiene diisocyanate composition obtained by reacting at a ratio of 1.5 to 1: 2.5, tetrabasic acid dianhydride, functional group equivalent X of the isocyanate group of the diisocyanate compound as a raw material, raw material The functional group equivalent W of the hydroxyl group of the bifunctional hydroxyl-terminated polybutadiene and the functional group equivalent Y of the acid anhydride group of the tetrabasic dianhydride are Y> X−W ≧ Y / 5 (W> 0, X> 0, Y> 0) is a linear modified polyimide resin obtained by reacting at a ratio satisfying the relationship of Y> 0). Grayed.
[5] The linear modified polyimide resin of the component (A) is a diisocyanate compound isocyanate which is a raw material of the linear modified polyimide resin according to any one of the above [1] to [4]. Functional group equivalent X, hydroxyl group functional group equivalent W of bifunctional hydroxyl-terminated polybutadiene as a raw material, functional group equivalent Y of acid anhydride group of tetrabasic acid dianhydride, and isocyanate functional group equivalent Z of newly reacted isocyanate compound Is a linear modified polyimide resin obtained by reacting at a ratio satisfying the relationship of Y- (X-W)> Z ≧ 0 (W> 0, X> 0, Y> 0, Z> 0), The prepreg according to any one of [1] to [4].
[6] (A) A linear modified polyimide resin having a polybutadiene structure represented by the following formula (1-a) and a polyimide structure represented by the following formula (1-b) in the molecule;
And (B) one or more thermosetting resins selected from epoxy resins, bismaleimide resins, cyanate ester resins, bisallyl nadiimide resins, vinyl benzyl ether resins, benzoxazine resins, and polymers of bismaleimides and diamines. A prepreg characterized in that a thermosetting resin composition contained is impregnated in a sheet-like reinforcing base material comprising fibers.
[ 7 ] The prepreg according to any one of [1] to [6] above, wherein the content of the polybutadiene structure in the linear modified polyimide resin of the component (A) is 60% by mass or more.
[ 8 ] The prepreg according to any one of the above [1] to [ 7 ], wherein R1 represents a residue excluding the hydroxyl group of a bifunctional hydroxyl group-terminated polybutadiene having a number average molecular weight of 800 to 10,000.
[ 9 ] The blending ratio of component (A) and component (B) is 100: 1 to 1: 1 by mass ratio, and the total content of component (A) and component (B) in the thermosetting resin composition is 70. The prepreg according to any one of the above [1] to [ 8 ], which is not less than mass%.
[ 10 ] The prepreg according to any one of [1] to [ 9 ], further containing a filler.
[ 11 ] The prepreg according to any one of [1] to [ 10 ] above, wherein the thermosetting resin of component (B) is an epoxy resin.
[ 12 ] The prepreg according to the above [ 11 ], further containing an epoxy curing agent.
[ 13 ] The prepreg according to any one of [1] to [ 12 ] above, wherein the thickness of the sheet-like fiber base material is 50 μm or less.
[ 14 ] A multilayer printed wiring board in which a part or all of the insulating layer is formed of a cured product of the prepreg according to any one of [1] to [ 13 ].
[ 15 ] A flexible circuit board in which a circuit is formed on a cured product of the prepreg according to any one of [1] to [ 13 ].
[ 16 ] A semiconductor device in which a semiconductor and a substrate substrate are bonded via a cured product of the thermosetting resin composition according to any one of [1] to [ 13 ].
Claims (16)
及び（Ｂ）エポキシ樹脂、ビスマレイミド樹脂、シアネートエステル樹脂、ビスアリルナジイミド樹脂、ビニルベンジルエーテル樹脂、ベンゾオキサジン樹脂及びビスマレイミドとジアミンの重合物から選択される１種以上の熱硬化性樹脂を含有する熱硬化性樹脂組成物が繊維からなるシート状補強基材中に含浸されていることを特徴とするプリプレグ。(A) a linear modified polyimide resin having a polybutadiene structure represented by the following formula (1-a) and a polyimide structure represented by the following formula (1-b) in the molecule;
And (B) one or more thermosetting resins selected from epoxy resins, bismaleimide resins, cyanate ester resins, bisallyl nadiimide resins, vinyl benzyl ether resins, benzoxazine resins, and polymers of bismaleimides and diamines. A prepreg characterized in that a thermosetting resin composition contained is impregnated in a sheet-like reinforcing base material comprising fibers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005368905A JP4986256B2 (en) | 2005-12-21 | 2005-12-21 | Prepreg containing modified polyimide resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005368905A JP4986256B2 (en) | 2005-12-21 | 2005-12-21 | Prepreg containing modified polyimide resin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007169454A JP2007169454A (en) | 2007-07-05 |
| JP2007169454A5 true JP2007169454A5 (en) | 2009-02-26 |
| JP4986256B2 JP4986256B2 (en) | 2012-07-25 |
Family
ID=38296448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005368905A Active JP4986256B2 (en) | 2005-12-21 | 2005-12-21 | Prepreg containing modified polyimide resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4986256B2 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI412560B (en) * | 2007-06-14 | 2013-10-21 | Ajinomoto Kk | And a resin composition for interlayer insulation of a multilayer printed wiring board |
| JP5369950B2 (en) * | 2009-07-10 | 2013-12-18 | 凸版印刷株式会社 | Multilayer printed wiring board manufacturing method and multilayer printed wiring board |
| WO2012124780A1 (en) * | 2011-03-16 | 2012-09-20 | 東レ株式会社 | Epoxy resin composition, method for producing same, and semiconductor device using same |
| JP5654912B2 (en) * | 2011-03-18 | 2015-01-14 | パナソニックＩｐマネジメント株式会社 | IMIDE RESIN COMPOSITION AND PROCESS FOR PRODUCING THE SAME, PREPREG, METAL-CLEAN LAMINATE, AND PRINTED WIRING BOARD |
| JP5161993B2 (en) | 2011-03-31 | 2013-03-13 | 株式会社東芝 | Electronics |
| KR101722208B1 (en) * | 2011-07-28 | 2017-05-02 | 주식회사 프로타빅 코리아 | Hybrid hot-setting adhensive composition |
| US20140154939A1 (en) * | 2011-10-18 | 2014-06-05 | Qianping Rong | Halogen-free low-dielectric resin composition, and prepreg and copper foil laminate made by using same |
| JP6108561B2 (en) * | 2012-10-11 | 2017-04-05 | 国立大学法人横浜国立大学 | Thermosetting resin and thermosetting resin composition |
| JP6287840B2 (en) | 2013-04-16 | 2018-03-07 | 東洋紡株式会社 | Metal foil laminate |
| JP6301473B2 (en) | 2013-09-30 | 2018-03-28 | エルジー・ケム・リミテッド | Thermosetting resin composition for semiconductor package, prepreg and metal foil laminate using the same |
| CN114103306B (en) * | 2021-11-05 | 2023-08-01 | 江苏耀鸿电子有限公司 | Halogen-free lead-free high-Tg copper-clad plate and processing technology thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4016226B2 (en) * | 1998-01-14 | 2007-12-05 | 味の素株式会社 | Modified polyimide resin and thermosetting resin composition containing the same |
| JP2000260900A (en) * | 1999-03-04 | 2000-09-22 | Mitsubishi Gas Chem Co Inc | Substrate for semiconductor plastic package |
| JP4231748B2 (en) * | 2003-07-10 | 2009-03-04 | 太陽インキ製造株式会社 | Prepreg for printed wiring board and multilayer printed wiring board produced using the same |
| JP4192054B2 (en) * | 2003-07-31 | 2008-12-03 | ユニチカ株式会社 | Super lightweight glass cloth |
| JP2005281663A (en) * | 2004-03-04 | 2005-10-13 | Hitachi Chem Co Ltd | Prepreg and metal foil-clad laminate and printed circuit board using the same |
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2005
- 2005-12-21 JP JP2005368905A patent/JP4986256B2/en active Active
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