JP6756083B2 - 半導体パッケージ用樹脂組成物とこれを用いたプリプレグおよび金属箔積層板 - Google Patents
半導体パッケージ用樹脂組成物とこれを用いたプリプレグおよび金属箔積層板 Download PDFInfo
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- JP6756083B2 JP6756083B2 JP2019506376A JP2019506376A JP6756083B2 JP 6756083 B2 JP6756083 B2 JP 6756083B2 JP 2019506376 A JP2019506376 A JP 2019506376A JP 2019506376 A JP2019506376 A JP 2019506376A JP 6756083 B2 JP6756083 B2 JP 6756083B2
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007602 hot air drying Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- NAKOELLGRBLZOF-UHFFFAOYSA-N phenoxybenzene;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.C=1C=CC=CC=1OC1=CC=CC=C1 NAKOELLGRBLZOF-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
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Description
本出願は2017年3月22日付韓国特許出願第10−2017−0036104号および2018年2月13日付韓国特許出願第10−2018−0018018号に基づいた優先権の利益を主張し、当該韓国特許出願の文献に開示されたすべての内容は本明細書の一部として含まれている。
[化学式1]
前記炭素数1〜10のアルキレン基、炭素数1〜6のアルキル基、炭素数6〜15のアリール基、および炭素数2〜20のヘテロアリール基は、それぞれ独立してニトロ基、シアノ基およびハロゲン基からなる群より選ばれた1種以上の官能基に置換され、
[化学式2]
[化学式3]
[化学式1−1]
[化学式2−1]
[化学式3−1]
当量比=前記アミン硬化剤に含有された総活性水素当量/前記熱硬化性樹脂に含有された総硬化性官能基当量
[化学式5]
Rは、
nは、0または1〜50の整数である。
[化学式6]
Rは、HまたはCH3であり、
nは、0または1〜50の整数である。
[化学式7]
nは、0または1〜50の整数である。
[化学式13]
R1およびR2は、それぞれ独立して、H,CH3またはC2H5である。
[化学式14]
nは、0または1〜50の整数である。
[化学式17]
nは、0または1〜50の整数である。
下記の表1および表2の組成に従い、各成分をメチルエチルケトンに固形分65%に合わせて投入して混合した後、400rpm速度で一日間常温撹はんして実施例1〜5、比較例1〜6の半導体パッケージ用樹脂組成物(樹脂ワニス)を製造した。具体的には、前記実施例1〜5で製造した樹脂組成物の具体的な組成は、下記の表1に記載されたとおりであり、前記比較例1〜6で製造された樹脂組成物の具体的な組成は、下記の表2に記載されたとおりである。
前記製造された半導体パッケージ用樹脂組成物(樹脂ワニス)を厚さ15μmのガラス繊維(Nittobo社製、T−glass #1017)に含浸させた後、170℃の温度で2〜5分間熱風乾燥して25μmのプリプレグを製造した。
*TFB:2,2'−bis(trifluoromethyl)benzidine;2,2'−Bis(trifluoromethyl)−4,4'−biphenyldiamine
*DDM:4,4'−diaminodiphenyl methane
*DDE:4,4'−diaminodiphenyl ether
*TDA:4,4'−Thiodianiline;4,4'−diaminodiphenyl sulfide
*XD−1000:エポキシ樹脂(Nippon kayaku社)
*NC−3000H:エポキシ樹脂(Nippon kayaku社)
*HP−6000:ナフタレン系エポキシ樹脂(DIC社)
*BMI−2300:ビスマレイミド樹脂(DAIWA KASEI社)
*SC2050MTO:フェニルアミノシラン処理したスラリータイプのマイクロシリカ、平均粒径0.5μm(Admantechs社)
*当量比:下記の数学式1により計算される
[数学式1]
熱硬化性樹脂に対するアミン硬化剤の当量比=(DDSの総活性水素当量+TFBの総活性水素当量+DDMの総活性水素当量+DDEの総活性水素当量+TDAの総活性水素当量)/{(XD−1000の総エポキシ当量+NC−3000Hの総エポキシ当量+HP−6000の総エポキシ当量)+(BMI−2300の総マレイミド当量)}
前記数学式1において、DDSの総活性水素当量は、DDSの総重量(g)をDDSの活性水素単位当量(62g/eq)で割った値であり、
TFBの総活性水素当量は、TFBの総重量(g)をTFBの活性水素単位当量(80g/eq)で割った値であり、
DDMの総活性水素当量は、DDMの総重量(g)をDDMの活性水素単位当量(49.5g/eq)で割った値であり、
DDEの総活性水素当量は、DDEの総重量(g)をDDEの活性水素単位当量(50g/eq)で割った値であり、
TDAの総活性水素当量は、TDAの総重量(g)をTDAの活性水素単位当量(54g/eq)で割った値であり、
XD−1000の総エポキシ当量は、XD−1000の総重量(g)をXD−1000のエポキシ単位当量(253g/eq)で割った値であり、
NC−3000Hの総エポキシ当量は、NC−3000Hの総重量(g)をNC−3000Hのエポキシ単位当量(290g/eq)で割った値であり、
HP−6000の総エポキシ当量は、HP−6000の総重量(g)をHP−6000のエポキシ単位当量(250g/eq)で割った値であり、
BMI−2300の総マレイミド当量は、BMI−2300の総重量(g)をBMI−2300のマレイミド単位当量(179g/eq)で割った値である。
*TFB:2,2'−bis(trifluoromethyl)benzidine;2,2'−Bis(trifluoromethyl)−4,4'−biphenyldiamine
*DDM:4,4'−diaminodiphenyl methane
*DDE:4,4'−diaminodiphenyl ether
*TDA:4,4'−Thiodianiline;4,4'−diaminodiphenyl sulfide
*XD−1000:エポキシ樹脂(Nippon kayaku社)
*NC−3000H:エポキシ樹脂(Nippon kayaku社)
*HP−6000:エポキシ樹脂(DIC社)
*BMI−2300:ビスマレイミド系樹脂(DAIWA KASEI社)
*SC2050MTO:フェニルアミノシラン処理したスラリータイプのマイクロシリカ、平均粒径0.5μm(Admantechs社)
*当量比:前記表1と同様の数学式1により計算
前記実施例および比較例で得られた半導体パッケージ用樹脂組成物、プリプレグおよび銅箔積層板の物性を下記方法で測定し、その結果を表3に示した。
前記実施例および比較例で得られた銅箔積層板の銅箔層をエッチングして除去した後、MD方向に試験片を製作し、TMA(TA Instruments,Q400)を用いて、30℃から260℃まで、昇温速度10℃/minの条件で測定した後、50℃から150℃範囲の測定値を熱膨張係数として記録した。
IPC−TM−650(2.3.17)に準拠して、前記実施例および比較例で得られたプリプレグ状態でカーバープレス(Carver社、#3893.4NE0000)を用いてRFを測定した。
IPC−TM−650(2.3.17)に準拠して、前記実施例および比較例で得られたプリプレグを常温で1月間保管した後の状態でカーバープレス(Carver社、#3893.4NE0000)を用いてRFを測定した。
前記実施例および比較例で得られたプリプレグを、回路パターン(パターン高さ10um、残銅率50%)の両面に位置させ、その上に銅箔(厚さ12μm、Mitsui社製)を位置させ、220℃および35kg/cm2の条件で100分間プレスした後、両面の銅箔をエッチングして、次の基準下で回路パターン充填性を評価した。
○:Void発生なし
X:Void発生
前記実施例および比較例で得られたプリプレグに対して、レオメータ(Anton Paar社、Modular compact Rheometer MCR 302)を用いて、50℃から200℃まで、昇温速度5℃/min、Normal Force 5N、Frequency 10Hz,amplitude 0.5%の条件で測定して粘度を評価し、最小粘度および最小粘度を現わす温度を記録した。
前記実施例および比較例で得られたプリプレグをガラス繊維のMDおよびTD方向が一致するように10枚を積層し、220℃および35kg/cm2の条件で100分間プレスした後、IPC−TM−650(2.4.18.3)に準拠し、Universal Testing Machine(Instron 3365)装備を用いてMD方向の引張伸び率を測定した。
Claims (7)
- スルホン基またはトリフルオロメチル基を含むアミン硬化剤;
熱硬化性樹脂;および
無機充填剤を含み、
前記アミン硬化剤は、4,4'−diaminodiphenyl sulfoneまたは2,2'−bis(trifluoromethyl)benzidineであり、
前記熱硬化性樹脂は、エポキシ樹脂およびビスマレイミド樹脂を含み、
前記エポキシ樹脂は、ナフタレン系エポキシ樹脂、ビフェニル系エポキシ樹脂、およびジシクロペンタジエン系エポキシ樹脂からなる群より選ばれた1種以上であり、
前記ビスマレイミド樹脂は、フェニルメタン型マレイミド樹脂のオリゴマーであり、
前記無機充填剤はシリカであり、前記シリカは、表面にシラン化合物が結合した平均粒径0.1μm〜100μmのシリカを含み、
前記アミン硬化剤および熱硬化性樹脂100重量部に対して前記無機充填剤の含有量が200重量部〜500重量であり、
前記アミン硬化剤100重量部に対して前記熱硬化性樹脂の含有量が150重量部〜400重量部であり、
下記の数学式1で計算される当量比が1.4〜2.5である、
半導体パッケージ用樹脂組成物:
[数学式1]
当量比=前記アミン硬化剤に含有された総活性水素当量/前記熱硬化性樹脂に含有された総硬化性官能基当量。 - 前記シラン化合物は、アミノシランカップリング剤、エポキシシランカップリング剤、ビニルシランカップリング剤、陽イオンシランカップリング剤およびフェニルシランカップリング剤からなる群より選ばれた1種以上のシランカップリング剤を含む、
請求項1に記載の半導体パッケージ用樹脂組成物。 - 前記半導体パッケージ用樹脂組成物は、IPC−TM−650(2.3.17)に準拠して測定した樹脂の流れ性が10%〜25%である、
請求項1または2に記載の半導体パッケージ用樹脂組成物。 - 前記半導体パッケージ用樹脂組成物は、145℃〜165℃で最小粘度を有し、前記最小粘度が100Pa・s〜500Pa・sである、
請求項1から3のいずれか一項に記載の半導体パッケージ用樹脂組成物。 - 前記半導体パッケージ用樹脂組成物は、IPC−TM−650(2.4.18.3)に準拠して測定した引張伸び率が2.0%〜5.0%である、
請求項1から4のいずれか一項に記載の半導体パッケージ用樹脂組成物。 - 請求項1から5のいずれか一項に記載の半導体パッケージ用樹脂組成物を繊維基材に含浸させて得られた
半導体パッケージ用プリプレグ。 - 請求項6に記載の半導体パッケージ用プリプレグ;および
加熱および加圧によって前記半導体パッケージ用プリプレグと一体化した金属箔;
を含む
金属箔積層板。
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