JP2019501237A - ポリマーゲッター材料を有するバリア接着剤 - Google Patents
ポリマーゲッター材料を有するバリア接着剤 Download PDFInfo
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- JP2019501237A JP2019501237A JP2018523466A JP2018523466A JP2019501237A JP 2019501237 A JP2019501237 A JP 2019501237A JP 2018523466 A JP2018523466 A JP 2018523466A JP 2018523466 A JP2018523466 A JP 2018523466A JP 2019501237 A JP2019501237 A JP 2019501237A
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- Prior art keywords
- adhesive
- barrier
- polymer
- groups
- barrier adhesive
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 135
- 239000000853 adhesive Substances 0.000 title claims abstract description 134
- 230000004888 barrier function Effects 0.000 title claims abstract description 69
- 229920000642 polymer Polymers 0.000 title claims abstract description 63
- 239000000463 material Substances 0.000 title description 22
- 229920005989 resin Polymers 0.000 claims abstract description 40
- 239000011347 resin Substances 0.000 claims abstract description 40
- 229920001971 elastomer Polymers 0.000 claims abstract description 28
- 239000000806 elastomer Substances 0.000 claims abstract description 23
- 125000000524 functional group Chemical group 0.000 claims abstract description 19
- 239000002390 adhesive tape Substances 0.000 claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 9
- 238000007789 sealing Methods 0.000 claims abstract description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 150000004292 cyclic ethers Chemical group 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 6
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- 229920001400 block copolymer Polymers 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 41
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 3
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- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HLQNHQOKIVRFLM-UHFFFAOYSA-N 3-[1-[1-(oxetan-3-yl)propoxy]propyl]oxetane Chemical compound C1OCC1C(CC)OC(CC)C1COC1 HLQNHQOKIVRFLM-UHFFFAOYSA-N 0.000 description 2
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 2
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 2
- MCDBEBOBROAQSH-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C=C MCDBEBOBROAQSH-UHFFFAOYSA-N 0.000 description 2
- JBDMKOVTOUIKFI-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(C)CCCOC(=O)C(C)=C JBDMKOVTOUIKFI-UHFFFAOYSA-N 0.000 description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- FYYIUODUDSPAJQ-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 2-methylprop-2-enoate Chemical compound C1C(COC(=O)C(=C)C)CCC2OC21 FYYIUODUDSPAJQ-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
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- XHNHTGPYLHOQRA-UHFFFAOYSA-M bis(2-dodecylphenyl)iodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCCCCCCCCCCC1=CC=CC=C1[I+]C1=CC=CC=C1CCCCCCCCCCCC XHNHTGPYLHOQRA-UHFFFAOYSA-M 0.000 description 2
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 2
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- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 2
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- PLDLPVSQYMQDBL-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propoxy]methyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(COCC1OC1)COCC1CO1 PLDLPVSQYMQDBL-UHFFFAOYSA-N 0.000 description 1
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- JSOZORWBKQSQCJ-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(C)CCCOC(=O)C(C)=C JSOZORWBKQSQCJ-UHFFFAOYSA-N 0.000 description 1
- UHGUVHWPYAIDNM-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propyl but-2-enoate Chemical compound CCO[Si](C)(C)CCCOC(=O)C=CC UHGUVHWPYAIDNM-UHFFFAOYSA-N 0.000 description 1
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- WRQOPPZJPSGEDO-UHFFFAOYSA-N 5-oxabicyclo[4.1.0]heptane Chemical compound C1CCOC2CC21 WRQOPPZJPSGEDO-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
−Si(OR1)xR2 3−x (I)
に対応する。
・スルホニウム塩、例えば、トリフェニルスルホニウムヘキサフルオロヒ酸塩、トリフェニルスルホニウムヘキサフルオロボレート、トリフェニルスルホニウムテトラフルオロボレート、メチルジフェニルスルホニウムテトラフルオロボレート、ジメチルフェニルスルホニウムヘキサフルオロホスフェート、トリフェニルスルホニウムヘキサフルオロホスフェート、トリフェニルスルホニウムヘキサフルオロアンチモネート、ジフェニルナフチルスルホニウムヘキサフルオロヒ酸塩、トリトリルスルホニウムヘキサフルオロホスフェート、アニシルジフェニルスルホニウムヘキサフルオロアンチモネート、4−ブトキシフェニルジフェニルスルホニウムテトラフルオロボレート、4−クロロフェニルジフェニルスルホニウムヘキサフルオロアンチモネート、トリス−(4−フェノキシフェニル)−スルホニウムヘキサフルオロホスフェート、ジ−(4−エトキシフェニル)−メチルスルホニウムヘキサフルオロヒ酸塩、4−アセチルフェニルジフェニルスルホニウムテトラフルオロボレート、トリス−(4−チオメトキシフェニル)−スルホニウムヘキサフルオロホスフェート、ジ−(メトキシスルフォニルフェニル)−メチルスルホニウムヘキサフルオロアンチモネート、ジ−(メトキシナフチル)−メチルスルホニウムテトラフルオロボレート、ジ−(カルボメトキシフェニル)−メチルスルホニウムヘキサフルオロホスフェート、(4−オクチルオキシフェニル)−ジフェニルスルホニウムテトラキス−(3,5−ビス−トリフルオロメチルフェニル)−ボレート、トリス−(ドデシルフェニル)−スルホニウムテトラキス−(3,5−ビス−トリフルオロメチルフェニル)−ボレート、4−アセトアミドフェニルジフェニルスルホニウムテトラフルオロボレート、ジメチルナフチルスルホニウムヘキサフルオロホスフェート、トリフルオロメチルジフェニルスルホニウムテトラフルオロボレート、フェニルメチルベンジルスルホニウムヘキサフルオロホスフェート、5−メチルチアントレニウムヘキサフルオロホスフェート、10−フェニル−9,9−ジメチルチオキサンテニウムヘキサフルオロホスフェート、10−フェニル−9−オキソチオキサンテニウムテトラフルオロボレート、5−メチル−10−オキソチアントレニウムテトラフルオロボレートおよび5−メチル−10,10−ジオキソチアントレニウムヘキサフルオロホスフェート。
ジ−(4−メチルフェニル)−ヨードニウムテトラフルオロボレート、
フェニル−4−メチルフェニルヨードニウムテトラフルオロボレート、
ジ−(4−クロロフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジナフチルヨードニウムテトラフルオロボレート、
ジ−(4−トリフルオロメチルフェニル)−ヨードニウムテトラフルオロボレート、ジフェニルヨードニウムヘキサフルオロホスフェート、ジ−(4−メチルフェニル)−ヨードニウムヘキサフルオロホスフェート、ジフェニルヨードニウムヘキサフルオロヒ酸塩、
ジ−(4−フェノキシフェニル)−ヨードニウムテトラフルオロボレート、
フェニル−2−チエニルヨードニウムヘキサフルオロホスフェート、
3,5−ジメチルピラゾリル−4−フェニルヨードニウムヘキサフルオロホスフェート、ジフェニルヨードニウムヘキサフルオロアンチモネート、2,2’−ジフェニルヨードニウムテトラフルオロボレート、
ジ−(2,4−ジクロロフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジ−(4−ブロモフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジ−(4−メトキシフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジ−(3−カルボキシフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジ−(3−メトキシカルボニルフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジ−(3−メトキシスルフォニルフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジ−(4−アセトアミドフェニル)−ヨードニウムヘキサフルオロホスフェート、
ジ−(2−ベンゾチエニル)−ヨードニウムヘキサフルオロホスフェート、ジアリールヨードニウムトリトリフルオロメチルスルフォニルメタイド、例えば、ジフェニルヨードニウムヘキサフルオロアンチモネート、
(4−n−デシロキシフェニル)−フェニルヨードニウムヘキサフルオロアンチモネート、
[4−(2−ヒドロキシ−n−テトラデシロキシ)−フェニル]−フェニルヨードニウムヘキサフルオロアンチモネート、
[4−(2−ヒドロキシ−n−テトラデシロキシ)−フェニル]−フェニルヨードニウムテトラフルオロスルホネート、
[4−(2−ヒドロキシ−n−テトラデシロキシ)−フェニル]−フェニルヨードニウムヘキサフルオロホスフェート、
ビス−(4−tert−ブチルフェニル)−ヨードニウムヘキサフルオロアンチモネート、
ビス−(4−tert−ブチルフェニル)−ヨードニウムヘキサフルオロホスフェート、
ビス−(4−tert−ブチルフェニル)−ヨードニウムトリフルオロスルホネート、
ビス−(4−tert−ブチルフェニル)−ヨードニウムテトラフルオロボレート、
ビス−(ドデシルフェニル)−ヨードニウムヘキサフルオロアンチモネート、
ビス−(ドデシルフェニル)−ヨードニウムテトラフルオロボレート、
ビス−(ドデシルフェニル)−ヨードニウムヘキサフルオロホスフェート、
ビス−(ドデシルフェニル)−ヨードニウムトリフルオロめちるスルホネート、
ジ−(ドデシルフェニル)−ヨードニウムヘキサフルオロアンチモネート、ジ−(ドデシルフェニル)−ヨードニウムトリフレート、ジフェニルヨードニウムビスルフェート、4,4’−ジクロロジフェニルヨードニウムビスルフェート、
4,4’−ジブロモジフェニルヨードニウムビスルフェート、3,3’−ジニトロジフェニルヨードニウムビスルフェート、
4,4’−ジメチルジフェニルヨードニウムビスルフェート、4,4’−ビス−スクシンイミドジフェニルヨードニウムビスルフェート、
3−ニトロジフェニルヨードニウムビスルフェート、4,4’−ジメトキシジフェニルヨードニウムビスルフェート、および
(4−オクチルオキシフェニル)−フェニルヨードニウムテトラキス−(3,5−bis−トリフルオロメチルフェニル)−ボレート、および
・フェロセニウム塩、例えば、η5−(2,4−シクロペンタジエン−1−イル)−[(1−メチルエチル)ベンゼン(1,2,3,4,5,6,9)]鉄。
ブレイクスルー時間の測定
寿命試験
エレクトロニクスデバイスの寿命の測定の尺度として、カルシウム試験を用いた。これを図1に示す。このために、10×10mm2の薄いカルシウム層23をガラスプレート21上に真空中で堆積させ、次いで窒素雰囲気下で貯蔵した。カルシウム層23の厚さは約100nmであった。カルシウム層23のカプセル化のために、試験される接着剤22および支持材料として薄いガラスディスク24(35μm、Schott社)を有する接着テープ(23×23mm2)を使用した。薄いガラスディスクを安定化させるために、光学的に透明性の高いアクリレート粘着剤からなる、50μmの厚さの転写型接着テープ25を用いて厚さ100μmのPETフィルム26をラミネートした。接着剤22を、接着剤22がカルシウムミラー23をその縁部が6.5mm(A−A)突出して覆うようにガラスプレート21上に適用した。不透明なガラス支持体24のために、感圧接着剤を介した、または境界面に沿った透過物のみが測定された。
接着剤層を製造するために、種々の接着剤を、溶液から、ラボラトリーコーターを用いて慣用的なライナー(シリコーン処理したポリエステルフィルム)に塗布し、乾燥させた。乾燥後の接着剤層の厚さは50±5μmであった。乾燥は、実験室乾燥キャビネット内で、最初に室温で10分間、そして、120℃で10分間行った。乾燥した接着剤層は、乾燥後直ちに、それぞれ、その開放面上を第二のライナー(より低い剥離力を有するシリコーン処理したポリエステルフィルム)でラミネートした。
Claims (14)
- −少なくとも一つのエラストマーおよび
−少なくとも一つの反応性樹脂、
を含む、バリア接着剤であって、
該バリア接着剤が、ポリマーの形成に適した少なくとも二つの官能基および少なくとも二つの加水分解性シリル基を含む、少なくとも一つのポリマーGを含むことを特徴とする、上記のバリア接着剤。 - 前記少なくとも一つのポリマーGが、ポリアクリレート骨格を有することを特徴とする、請求項1に記載のバリア接着剤。
- 前記ポリマーを形成するのに適した官能基が、ビニル基、(メタ)アクリレート基、ヒドロキシ基、アミノ基、イソシアネート基、環状エーテル基およびエポキシ基からなる群から互いに独立して選択されることを特徴とする、請求項1または2に記載のバリア接着剤。
- 前記ポリマーを形成するのに適した官能基が、(メタ)アクリレート基およびエポキシ基から、互いに独立して選択されることを特徴とする、請求項1〜3のいずれか一つに記載のバリア接着剤。
- 前記ポリマーを形成するのに適した官能基が、エポキシシクロアルキル基を含むことを特徴とする、請求項1〜4のいずれか一つに記載のバリア接着剤。
- 前記加水分解性シリル基が、次の式(I)、
−Si(OR1)xR2 3−x (I)
(式中、置換基R1は、互いに独立して、メチル残基またはエチル残基を表し、置換基R2は、互いに独立して、アルキル残基またはアリール残基を表し、そしてx=1〜3である。)
に相当することを特徴とする、請求項1〜5のいずれか一つに記載のバリア接着剤。 - 置換基R1が、エチル残基を表すことを特徴とする、請求項6に記載のバリア接着剤。
- x=2または3であることを特徴とする、請求項6または7に記載のバリア接着剤。
- 前記少なくとも一つのエラストマーが、ビニル芳香族ブロックコポリマーであることを特徴とする、請求項1〜8のいずれか一つに記載のバリア接着剤。
- 前記少なくとも一つの反応性樹脂が、環状エーテル基を含有することを特徴とする、請求項1〜9のいずれか一つに記載のバリア接着剤。
- 前記接着剤が、前記バリア接着剤の全重量に基づいて、合計して15〜80重量%の反応性樹脂を含有することを特徴とする、請求項1〜10のいずれか一つに記載のバリア接着剤。
- 前記バリア接着剤が、粘着剤であることを特徴とする、請求項1〜11のいずれか一つに記載のバリア接着剤。
- 請求項12に記載のバリア接着剤を含む接着テープ。
- 請求項1〜12のいずれか一つに記載のバリア接着剤の、エレクトロニクスデバイスを封止するための使用。
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-
2015
- 2015-11-09 DE DE102015222027.3A patent/DE102015222027A1/de not_active Withdrawn
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2016
- 2016-10-25 KR KR1020187016197A patent/KR102182486B1/ko active IP Right Grant
- 2016-10-25 CN CN201680065405.0A patent/CN108350333B/zh active Active
- 2016-10-25 JP JP2018523466A patent/JP2019501237A/ja not_active Withdrawn
- 2016-10-25 WO PCT/EP2016/075645 patent/WO2017080813A1/de active Application Filing
- 2016-10-25 US US15/770,424 patent/US10633563B2/en active Active
- 2016-10-25 EP EP16785491.8A patent/EP3374461B1/de active Active
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Also Published As
Publication number | Publication date |
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WO2017080813A1 (de) | 2017-05-18 |
EP3374461B1 (de) | 2019-10-09 |
DE102015222027A1 (de) | 2017-05-11 |
TW201734172A (zh) | 2017-10-01 |
CN108350333A (zh) | 2018-07-31 |
CN108350333B (zh) | 2020-05-12 |
TWI665278B (zh) | 2019-07-11 |
KR20180083881A (ko) | 2018-07-23 |
EP3374461A1 (de) | 2018-09-19 |
US10633563B2 (en) | 2020-04-28 |
US20180298241A1 (en) | 2018-10-18 |
KR102182486B1 (ko) | 2020-11-24 |
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