JP2020508363A - ポリイミド樹脂の接着性を増進させる化合物及びそれを用いて製造されたポリイミド共重合体 - Google Patents
ポリイミド樹脂の接着性を増進させる化合物及びそれを用いて製造されたポリイミド共重合体 Download PDFInfo
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- JP2020508363A JP2020508363A JP2019541765A JP2019541765A JP2020508363A JP 2020508363 A JP2020508363 A JP 2020508363A JP 2019541765 A JP2019541765 A JP 2019541765A JP 2019541765 A JP2019541765 A JP 2019541765A JP 2020508363 A JP2020508363 A JP 2020508363A
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
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- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 24
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
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Classifications
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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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
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- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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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
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- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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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
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- 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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- 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
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- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
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- C—CHEMISTRY; METALLURGY
- 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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- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/544—Silicon-containing compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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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Abstract
Description
[化学式1a]
[化学式2a]
[化学式6]
[化学式1a]
[化学式2a]
[化学式5a]
[化学式6]
[化学式7a]
[化学式8]
[化学式9]
[化学式10]
[式1]
ディウェッティング率(%)=[(A−B)/A]×100
前記式1において、A:基板(100mm×100mm)上にポリイミド前駆体組成物が完全にコーティングされた状態での面積であり、B:ポリイミド前駆体組成物またはPIフィルムがコーティングされた基板の縁部先端からディウェッティング現象が発生した後の面積である。
[反応式1]
Bruker 700MHz NMRを使用して、acetone−d6を満たしたインサートチューブ(insert tube)を使用して、原液のままのNMRスペクトルを測定した。
窒素気流が流れる反応器内にN,N−ジエチルアセトアミド(DEAc)(分配係数0.32)124gを満たした後、反応器の温度を25℃に保持した状態で両末端アミン変性DMS−DPS(分子量5700g/mol、p=73.3、q=26.7)0.0010molとTFMB(2,2'−ビス(トリフルオロメチル)ベンジジン)0.0390molとを同じ温度で添加して溶解させた。前記DMS−DPS及びTFMBが添加された溶液にPMDA 0.032mol及びBPAF(9,9'−ビス(3,4−ジカルボキシフェニル)フルオレン二無水物)0.008molを同じ温度で添加して、3時間撹拌した後、80℃で4時間撹拌した。
前記重合例1から製造されたポリイミド前駆体溶液にポリアミド酸100重量部を基準に合成例1から得られた化合物を0.5重量部添加した。
前記重合例1から製造されたポリイミド前駆体溶液にポリアミド酸100重量部を基準に合成例2から得られた化合物を0.5重量部添加した。
実施例1及び比較例1から製造されたそれぞれのポリイミド前駆体溶液をガラス基板上にスピンコーティングした。ポリイミド前駆体溶液が塗布されたガラス基板をオーブンに入れ、5℃/minの速度で加熱し、80℃で30分、400℃で30分を保持して、硬化工程を進行して、ポリイミドフィルムを製造した。
黄色度(YI)は、Color Eye 7000Aで測定した。
厚さ方向位相差(Rth)は、Axoscanを用いて測定した。フィルムを一定のサイズに切って、厚さを測定した後、Axoscanで位相差を測定して、位相差値を補償するために、C−plate方向に補正しながら測定した厚さ(nm)を入力した。
フィルムを5x20mmのサイズに切って、試料を準備した後、アクセサリーを用いて試料をローディングする。実際に測定されるフィルムの長さは、16mmに同様にした。フィルムを引っ張る力を0.02Nに設定し、100〜400℃の温度範囲で5℃/minの昇温速度で1次昇温工程を進行した後、400〜100℃の温度範囲で4℃/minの冷却速度で冷却(cooling)した後、再び100〜450℃の温度範囲で5℃/minの昇温速度で2次昇温工程を進行して、熱膨張変化態様をTMA(TA社のQ400)で測定した。
前記のような方法で製造されたポリイミドフィルムのピール強度(接着力)は、ピール強度測定計(TA−XT Plus、Texture Analyser)で、フィルム幅2.54cm、測定長さ10mmにサンプルを作って、10mm/secで90゜剥離時のピール強度を測定した。
Claims (14)
- 下記化学式1aまたは化学式1bで表される化合物:
[化学式1a]
X1及びX2は、それぞれ独立して置換または非置換の炭素数1〜30の3価の有機基であるか、互いに結合して置換または非置換の炭素数3〜30の4価の有機基であり、
X3及びX4は、それぞれ独立して置換または非置換の炭素数1〜30の2価の有機基であるか、互いに結合して置換または非置換の炭素数3〜30の3価の有機基であり、
R1及びR3は、それぞれ独立して炭素数1〜5のアルキル基であり、
R2及びR4は、それぞれ独立して水素原子または炭素数1〜5のアルキル基であり、
a及びbは、それぞれ独立して1〜3の整数であり、
n及びmは、それぞれ独立して0〜3の整数である。 - 重合成分として、酸二無水物、ジアミン及びジメチルシロキサン(DMS)−ジフェニルシロキサン(DPS)オリゴマーと、
25℃分配係数(LogP)が正数である溶媒と、
請求項1から4のいずれか一項に記載の化合物と、
を含むポリイミド前駆体組成物を重合及び硬化するステップを含む、ポリイミド共重合体の製造方法。 - 前記ポリイミド前駆体組成物100重量部に対して、請求項1に記載の化合物を0.1〜10重量部で含む請求項5または6に記載のポリイミド共重合体の製造方法。
- 前記酸二無水物1molに対して、請求項1に記載の化合物を0.001〜0.5mol比で含む請求項5から7のいずれか一項に記載のポリイミド共重合体の製造方法。
- 前記化学式6の構造を有するジアミン化合物の重量平均分子量が、4000g/mol以上である請求項6に記載のポリイミド共重合体の製造方法。
- 25℃分配係数(LogP)が正数である溶媒が、アミド系溶媒である請求項5から9のいずれか一項に記載のポリイミド共重合体の製造方法。
- 前記アミド系溶媒が、ジメチルプロピオンアミド(DMPA)、ジエチルプロピオンアミド(DEPA)、N,N−ジエチルアセトアミド(DEAc)、N,N−ジエチルホルムアミド(DEF)、N−エチルピロリドン(NEP)から選択される1つ以上である請求項10に記載のポリイミド共重合体の製造方法。
- 請求項5から11のいずれか一項に記載のポリイミド共重合体の製造方法を含む、ポリイミドフィルムの製造方法。
- 前記ポリイミドフィルムの位相差が、−500〜500nmである請求項12に記載のポリイミドフィルムの製造方法。
- 前記ポリイミドフィルムとキャリア基板との接着力が、5gf/in以上である請求項12または13に記載のポリイミドフィルムの製造方法。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4923948A (en) * | 1987-09-24 | 1990-05-08 | Japan Synthetic Rubber Co., Ltd. | Curable composition |
US5061809A (en) * | 1990-05-25 | 1991-10-29 | Air Products And Chemicals, Inc. | 9,9-bis-(3,4-dicarboxyphenyl)fluorene dianhydrides |
JP2009256293A (ja) * | 2008-03-26 | 2009-11-05 | Osaka Gas Co Ltd | フルオレン骨格を有するケイ素化合物 |
JP2009298995A (ja) * | 2008-06-17 | 2009-12-24 | Nippon Shokubai Co Ltd | 複合粒子、樹脂組成物、及び、その硬化物 |
US20150368402A1 (en) * | 2013-02-07 | 2015-12-24 | Kaneka Corporation | Alkoxysilane-modified polyamic acid solution, laminate and flexible device each produced using same, and method for producing laminate |
KR20160097685A (ko) * | 2015-02-09 | 2016-08-18 | 주식회사 엘지화학 | 폴리이미드계 필름 형성용 조성물 및 이를 이용하여 제조된 폴리이미드계 필름 |
KR20170057458A (ko) * | 2014-12-24 | 2017-05-24 | 유니티카 가부시끼가이샤 | 다공질 폴리이미드 필름 및 그의 제조 방법 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7625596B2 (en) | 2004-12-15 | 2009-12-01 | General Electric Company | Adhesion promoter, electroactive layer and electroactive device comprising same, and method |
WO2009117734A1 (en) | 2008-03-21 | 2009-09-24 | Enthone Inc. | Adhesion promotion of metal to laminate with a multi-functional compound haftforderung von metall zu laminaten mit einer multifunktionellen |
JP6010533B2 (ja) | 2011-06-13 | 2016-10-19 | 株式会社カネカ | ポリアミド酸、ポリイミド、ポリアミド酸溶液、ポリイミド溶液、およびこれらの溶液から得られるポリイミド膜、ならびにポリイミド膜の利用 |
KR20150021527A (ko) | 2012-05-28 | 2015-03-02 | 우베 고산 가부시키가이샤 | 폴리이미드 전구체 및 폴리이미드 |
KR20140144530A (ko) * | 2013-06-11 | 2014-12-19 | 주식회사 엘지화학 | 폴리이미드 수지 전구체 조성물, 드라이 필름 및 회로 기판 |
KR20140144529A (ko) | 2013-06-11 | 2014-12-19 | 주식회사 엘지화학 | 폴리이미드 수지의 접착 증진제 및 이의 제조방법 |
KR101955957B1 (ko) | 2015-04-17 | 2019-03-08 | 아사히 가세이 가부시키가이샤 | 수지 조성물, 폴리이미드 수지막, 및 그 제조 방법 |
KR101993647B1 (ko) | 2016-07-26 | 2019-09-30 | 주식회사 엘지화학 | 폴리이미드 전구체 용액 및 이의 제조방법 |
WO2018021747A1 (ko) * | 2016-07-26 | 2018-02-01 | 주식회사 엘지화학 | 폴리이미드 전구체 용액 및 이의 제조방법 |
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4923948A (en) * | 1987-09-24 | 1990-05-08 | Japan Synthetic Rubber Co., Ltd. | Curable composition |
US5061809A (en) * | 1990-05-25 | 1991-10-29 | Air Products And Chemicals, Inc. | 9,9-bis-(3,4-dicarboxyphenyl)fluorene dianhydrides |
JP2009256293A (ja) * | 2008-03-26 | 2009-11-05 | Osaka Gas Co Ltd | フルオレン骨格を有するケイ素化合物 |
JP2009298995A (ja) * | 2008-06-17 | 2009-12-24 | Nippon Shokubai Co Ltd | 複合粒子、樹脂組成物、及び、その硬化物 |
US20150368402A1 (en) * | 2013-02-07 | 2015-12-24 | Kaneka Corporation | Alkoxysilane-modified polyamic acid solution, laminate and flexible device each produced using same, and method for producing laminate |
KR20170057458A (ko) * | 2014-12-24 | 2017-05-24 | 유니티카 가부시끼가이샤 | 다공질 폴리이미드 필름 및 그의 제조 방법 |
KR20160097685A (ko) * | 2015-02-09 | 2016-08-18 | 주식회사 엘지화학 | 폴리이미드계 필름 형성용 조성물 및 이를 이용하여 제조된 폴리이미드계 필름 |
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