JP7089573B2 - ポリイミド-ポリアリーレンポリマー - Google Patents
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Description
本明細書で開示されるプロセス、手順、方法、生成物、結果、及び/又は概念(以下では集合的に「本開示」と称する)は、広義には、ポリマーを製造するためのモノマー成分として用いられ得る新規な有機化合物に関する。具体的には、官能化ビス-イミド化合物は、シクロペンタジエノン含有種と共重合されて、エレクトロニクス及びディスプレイ用途によく適した特性を備えるポリマーを生成することができる。
より従来型の現行の材料に勝る、これらの広範に変化可能な特性及び加工性の利点の結果、エレクトロニクス及びディスプレイ用途におけるポリマーの使用は益々増え続けている。ポリフェニレンポリマーは、1つのこうした材料の分類を代表する。これらは、多くのエレクトロニクス及びディスプレイ用途に求められる、良好な耐化学性と、高いTgと、機械的靱性との効果的な組み合わせを示すように製造され得る。更に、ポリフェニレンポリマーの分子量及び溶液濃度は、普遍的に重要な生産加工法であるスピンコーティングによる正確且つ便利な堆積を可能にするように調整され得る。硬化膜の芳香族炭化水素構造は、低い誘電率、高い熱安定性、及び低い吸湿性を提供する。ヘテロ原子の含有、コポリマー形成などによりもたらされる合成可撓性により、使用中の特異性の高い用途のために調製され得る材料のファミリ-が利用可能となる。
α=(ΔL/L0)/ΔT
X1及びyは同じか又は異なり、且つx1+yが2~6の整数となるような0~4の整数である。
この実施例は、式3を有するモノマーである化合物M2-1の調製を例示する。化合物M2-1は式3の実施形態であり、
この実施例は、ビス-イミドモノマー1a及びDPO-CPDに基づくポリマーであるポリマー1の調製を例示する。
メチル3-ブロモ-5-ニトロベンゾエートの調製。
3-ニトロ-5-(トリメチルシリルエチニル)ベンゾエートの調製。
3-エチニル-5-ニトロ安息香酸の調製。
3-アミノ-5-エチニル安息香酸の調製。
配合物を衝撃試験に供して、エレクトロニクス及びディスプレイ産業で一般に用いられている溶媒系とのこれらの相溶性を判定することによってポリマーの溶解度を評価した。ポリマーを、最初に、61.75:33.25:5の比のメチル3-メトキシプロピオネート(MMP)、アニソール、及びγ-ブチロラクトン(GBL)からなる溶媒系中に、12又は30重量%のいずれかの固体ポリマー濃度で配合し、続いて0.2μmのPTFEフィルタで濾過した。より粘性の高い溶液を、0.45μmのPTFEフィルタ又は5μmのナイロンフィルタで濾過した。試験溶媒系は、70:30比のプロピレングリコールモノメチルエーテル(PGME)とプロピレングリコールモノメチルエーテルアセテート(PGMEA)とから構成されていた。少量のポリマー配合物を、試験溶媒系に対して溶解して且つ30:1及び200:1で希釈することを試みることによって衝撃試験を実施した。続いて混合物をロール混合した。次に、両方の希釈の視覚検査のための表1の以下の基準に基づいて溶解度評点を割り当てた。いくつかの実施形態では、使用中の要件により、衝撃試験評点における4.5の合格閾値が設定される。
Claims (8)
- エチニル部分で置換された2つ以上のアリール部分、及びそれぞれ1つ以上の極性置換基を有する2つ以上のアリール部分を含むビス-イミド化合物であって、前記ビス-イミド化合物は、式1aを有する化合物、式1bを有する化合物、及び式1cを有する化合物からなる群から選択され、
L1は、(Z2)yで置換された二価の芳香族連結基であり、
L2はベンゼン環、縮合芳香族環又は脂環式環であり、
L3は二価の連結基であり、
Z1及びZ2は出現ごとに同じか又は異なり、且つ極性基であり、
Ar1は、出現ごとに同じか又は異なり、且つC6~C30アリール基からなる群から選択され、
x1、x2、x3、及びyは同じか又は異なり、且つ0~3の整数であり;
vは0~2の整数であるが、但し、L2が脂環式環である場合は、vは0であることを条件とし、
wは0~3の整数であり、
x1+yは2~6の整数であり、
x2+vは2~4の整数であり、
x3+wは2~6の整数であり、
ただし、前記式1aにおいて極性基Z 1 及びZ 2 は、OH、CO 2 H、CO 2 R、OR、CF 3 、F、Cl、SH、SR、S(O) n R、S(O) 2 OH、S(O) 2 OR、S 2 R、NR 2 、NH(O)R、及び
式中、
Rは、H、ハロゲン、C 1~30 アルキル、C 1~30 ヘテロアルキル、C 2~30 アルケニル、C 7~30 アラルキル、C 6~30 アリール、及びC 4~30 ヘテロアリールからなる群から選択され、並びに、
nは1~2の整数である、ビス-イミド化合物。 - L1は、炭化水素アリール基、ヘテロアリール基、及びこれらの置換誘導体からなる群から選択される、請求項1に記載のビス-イミド化合物。
- L2は、4~6員環の脂環式環、ベンゼン環、及びナフタレン環からなる群から選択される、請求項2に記載のビス-イミド化合物。
- Ar1は出現ごとに同じか又は異なり、且つC6~C18アリール基からなる群から選択される、請求項4に記載のビス-イミド化合物。
- (a)エチニル部分で置換された2つ以上のアリール部分と、それぞれ1つ以上の極性置換基を有する2つ以上のアリール部分と、を含むビス-イミド化合物を含む1つ以上の第1のモノマーであって、式1aを有する化合物、式1bを有する化合物、及び式1cを有する化合物からなる群から選択される1つ以上の第1のモノマーと、
L 1 は、(Z 2 ) y で置換された二価の芳香族連結基であり、
L 2 はベンゼン環、縮合芳香族環又は脂環式環であり、
L 3 は二価の連結基であり、
Z 1 及びZ 2 は出現ごとに同じか又は異なり、且つ極性基であり、
Ar 1 は、出現ごとに同じか又は異なり、且つC 6 ~C 30 アリール基からなる群から選択され、
x1、x2、x3、及びyは同じか又は異なり、且つ0~3の整数であり;
vは0~2の整数であるが、但し、L 2 が脂環式環である場合は、vは0であることを条件とし、
wは0~3の整数であり、
x1+yは2~6の整数であり、
x2+vは2~4の整数であり、及び、
x3+wは2~6の整数である。)
(b)2つ以上のシクロペンタジエノン部分を含む1つ以上の第2のモノマーであって、式3を有する1つ以上の第2のモノマーと、のモノマー混合物から重合されたコポリマーを含む、ポリマー組成物:
R 7 は、出現ごとに同じか又は異なり、且つH、置換もしくは非置換C 1~6 アルキル、置換もしくは非置換C 6~20 アリール、及び置換もしくは非置換C 4~20 ヘテロアリールからなる群から選択され、並びに、
Ar 2 は置換又は非置換C 6~20 アリール基である。)。
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