JP6906054B2 - 樹脂安定性及び耐熱性が向上し、透明性を有するポリイミド前駆体樹脂組成物、これを用いたポリイミドフィルムの製造方法、及びこれによって製造されたポリイミドフィルム - Google Patents
樹脂安定性及び耐熱性が向上し、透明性を有するポリイミド前駆体樹脂組成物、これを用いたポリイミドフィルムの製造方法、及びこれによって製造されたポリイミドフィルム Download PDFInfo
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- JP6906054B2 JP6906054B2 JP2019532897A JP2019532897A JP6906054B2 JP 6906054 B2 JP6906054 B2 JP 6906054B2 JP 2019532897 A JP2019532897 A JP 2019532897A JP 2019532897 A JP2019532897 A JP 2019532897A JP 6906054 B2 JP6906054 B2 JP 6906054B2
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- C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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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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Description
なお、本発明としては、以下の態様も好ましい。
〔1〕 芳香族ジアミン成分、酸二無水物化合物及び有機溶媒を含むポリイミド前駆体樹脂組成物であって、
前記芳香族ジアミン成分(A)はフッ素化芳香族ジアミン単量体である2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニル(TFMB)、又はアミド基を有するジアミン単量体であるN−(4−アミノフェニル)−4−アミノベンズアミド(DBA)、又はこれらの混合物を含み、
前記酸二無水物化合物(B)はフッ素化芳香族酸二無水物である4,4−(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(6FDA)と非フッ素化芳香族生酸二無水物であるピロメリット酸二無水物(PMDA)、又は3,3,4,4’−ビフェニルテトラカルボン酸二無水物(BPDA)を含む混合物であり、
前記有機溶媒(C)はガンマ−ブチロラクトン(GBL)及びN−メチル−2−ピロリドン(NMP)の混合物、又はガンマ−ブチロラクトン(GBL)及び3−メトキシ−N,N−ジメチルプロパンアミド(DMPA)の混合物、又は3−メトキシ−N,N−ジメチルプロパンアミド(DMPA)単独物であることを特徴とする、樹脂安定性及び高耐熱性が向上した透明ポリイミド前駆体樹脂組成物。
〔2〕 前記芳香族ジアミン成分(A)において、
2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニル(TFMB)は全体ジアミン化合物に対して30〜100モル%であり、
N−(4−アミノフェニル)−4−アミノベンズアミド(DBA)は全体ジアミン化合物に対して5〜50モル%であり、
残量の非フッ素化芳香族ジアミンをさらに含むことを特徴とする、〔1〕に記載の樹脂安定性及び高耐熱性が向上した透明ポリイミド前駆体樹脂組成物。
〔3〕 前記酸二無水物化合物(B)において、
フッ素化芳香族酸二無水物は全体酸二無水物化合物に対して20〜80モル%であり、
非フッ素化芳香族酸二無水物は全体酸二無水物化合物に対して80〜20モル%であることを特徴とする、〔1〕に記載の樹脂安定性及び高耐熱性が向上した透明ポリイミド前駆体樹脂組成物。
〔4〕 前記有機溶媒(C)は、ガンマ−ブチロラクトン(GBL)30〜70モル%とN−メチル−2−ピロリドン(NMP)又は3−メトキシ−N,N−ジメチルプロパンアミド(DMPA)70〜30モル%であることを特徴とする、〔1〕に記載の樹脂安定性及び高耐熱性が向上した透明ポリイミド前駆体樹脂組成物。
〔5〕 前記ポリイミド組成物は、トリメチルアミン(Trimethylamine)、キシレン(Xylene)、ピリジン(Pyridine)及びキノリン(Quinoline)からなる群から選択された1種以上の反応触媒(D)をさらに含むことを特徴とする、〔1〕に記載の樹脂安定性及び高耐熱性が向上した透明ポリイミド前駆体樹脂組成物。
〔6〕 〔1〕〜〔5〕のいずれか一項に記載の組成物から製造されたポリアミン酸溶液を熱処理してフィルムに製造することを特徴とする、透明ポリイミド樹脂フィルムの製造方法。
〔7〕 前記ポリアミン酸溶液は、固形分含量10〜40wt%の条件を基準に、有機溶媒含量を使い、芳香族ジアミン成分95〜100モル%及び酸二無水物化合物100〜105モル%を混合して製造されたことを特徴とする、〔6〕に記載の透明ポリイミド樹脂フィルムの製造方法。
〔8〕 前記ポリアミン酸溶液は1000〜7000cPであることを特徴とする、〔6〕に記載の透明ポリイミド樹脂フィルムの製造方法。
〔9〕 〔6〕に記載の方法で製造されたフィルムの厚さ10〜15μmを基準に、ガラス転移温度が300℃以上、100〜300℃範囲での熱膨張係数が25ppm/℃以下、550nmの波長での透過率が85%以上、550nm波長での黄色度指数(Yellow Index、Y.I.)が7以下であることを特徴とする、透明ポリイミド樹脂フィルム。
Claims (7)
- 芳香族ジアミン成分(A)、酸二無水物化合物(B)及び有機溶媒(C)を含む透明ポリイミド前駆体樹脂組成物であって、
前記芳香族ジアミン成分(A)は、フッ素化芳香族ジアミン単量体として2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニル(TFMB)を含み、
前記酸二無水物化合物(B)は、フッ素化芳香族酸二無水物として4,4’−(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(6FDA)、及び非フッ素化芳香族酸二無水物としてピロメリット酸二無水物(PMDA)又は3,3,4,4’−ビフェニルテトラカルボン酸二無水物(BPDA)を含む混合物であり、且つ
前記有機溶媒(C)は、ガンマ−ブチロラクトン(GBL)とN−メチル−2−ピロリドン(NMP)を含む混合物であるか、或いはガンマ−ブチロラクトン(GBL)と3−メトキシ−N,N−ジメチルプロパンアミド(DMPA)を含む混合物であり、
ここで、
前記芳香族ジアミン成分(A)中のTFMBの量は50〜100モル%であり、
前記酸二無水物化合物(B)中の前記フッ素化芳香族酸二無水物は、40〜70モル%の量であり且つ前記酸二無水物化合物(B)中の前記非フッ素化芳香族酸二無水物は、30〜60モル%の量であり、
前記有機溶媒(C)は、30〜70モル%のガンマ−ブチロラクトン(GBL)と70〜30モル%の3−メトキシ−N,N−ジメチルプロパンアミド(DMPA)を含むか、或いは70モル%のガンマ−ブチロラクトン(GBL)と30モル%のN−メチル−2−ピロリドン(NMP)を含む、透明ポリイミド前駆体樹脂組成物。 - 前記芳香族ジアミン成分(A)が、
(A−1)全ジアミン化合物に対して100モル%の2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニル(TFMB)を含むか、又は
(A−2)全ジアミン化合物に対して50〜95モル%の2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニル(TFMB)と、全ジアミン化合物に対して5〜50モル%のN−(4−アミノフェニル)−4−アミノベンズアミド(DBA)とを含み、
前記(A−2)が、残量として非フッ素化芳香族ジアミンをさらに含んでいてもよい、
請求項1に記載の透明ポリイミド前駆体樹脂組成物。 - 前記ポリイミド前駆体樹脂組成物は、トリメチルアミン(Trimethylamine)、キシレン(Xylene)、ピリジン(Pyridine)及びキノリン(Quinoline)からなる群から選択された1種以上の反応触媒(D)をさらに含む、請求項1に記載の透明ポリイミド前駆体樹脂組成物。
- 請求項1〜3のいずれか一項に記載の組成物を用いて製造されたポリアミック酸溶液を熱処理してフィルムを製造することを含む、透明ポリイミド樹脂フィルムの製造方法。
- 前記ポリアミック酸溶液は、固形分含量が10〜40wt%となるように有機溶媒を含み、且つ、前記芳香族ジアミン成分と前記酸二無水物化合物とを前記酸二無水物化合物100〜105モルに対して前記芳香族ジアミン成分95〜100モルのモル比で混合することによって調製される、請求項4に記載の透明ポリイミド樹脂フィルムの製造方法。
- 前記ポリアミック酸溶液は1000〜7000cPの粘度を有する、請求項4に記載の透明ポリイミド樹脂フィルムの製造方法。
- 請求項1〜3のいずれか1項に記載のポリイミド前駆体樹脂組成物から形成されるポリイミド樹脂フィルムであって、前記ポリイミド樹脂フィルムが、10〜15μmのフィルムの厚さを基準として、300℃以上のガラス転移温度を有し、100〜300℃範囲で25ppm/℃以下の熱膨張係数を有し、550nmの波長で85%以上の透過率を有し、且つ550nm波長で7以下の黄色度指数(Yellow Index、Y.I.)を有する、前記ポリイミド樹脂フィルム。
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WO2015002273A1 (ja) * | 2013-07-05 | 2015-01-08 | 三菱瓦斯化学株式会社 | ポリイミド樹脂 |
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KR101869173B1 (ko) * | 2014-02-14 | 2018-06-19 | 아사히 가세이 가부시키가이샤 | 폴리이미드 전구체 및 그것을 함유하는 수지 조성물 |
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US10144847B2 (en) * | 2014-05-30 | 2018-12-04 | Lg Chem, Ltd. | Polyimide-based solution and polyimide-based film produced using same |
JP2016027085A (ja) * | 2014-06-26 | 2016-02-18 | デクセリアルズ株式会社 | ポリイミド、ポリアミド酸、及びそれらの製造方法、並びに感光性樹脂組成物 |
KR101994059B1 (ko) * | 2014-07-17 | 2019-06-27 | 아사히 가세이 가부시키가이샤 | 수지 전구체 및 그것을 함유하는 수지 조성물, 폴리이미드 수지막, 수지 필름 및 그 제조 방법 |
CN104151823B (zh) * | 2014-09-02 | 2019-02-26 | 长春聚明光电材料有限公司 | 聚酰亚胺薄膜及其制备方法 |
KR102158223B1 (ko) * | 2014-11-17 | 2020-09-22 | 에스케이이노베이션 주식회사 | 폴리아믹산 용액, 폴리이미드 필름, 및 그 제조방법 |
JP2016098260A (ja) * | 2014-11-18 | 2016-05-30 | 住友ベークライト株式会社 | ポリアミド溶液 |
WO2016147958A1 (ja) * | 2015-03-13 | 2016-09-22 | 旭化成株式会社 | ポリイミド前駆体樹脂組成物 |
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