JP2021534271A - 電子デバイスで使用するためのポリマー - Google Patents
電子デバイスで使用するためのポリマー Download PDFInfo
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- JP2021534271A JP2021534271A JP2021506713A JP2021506713A JP2021534271A JP 2021534271 A JP2021534271 A JP 2021534271A JP 2021506713 A JP2021506713 A JP 2021506713A JP 2021506713 A JP2021506713 A JP 2021506713A JP 2021534271 A JP2021534271 A JP 2021534271A
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- 229920000642 polymer Polymers 0.000 title description 27
- 229920001721 polyimide Polymers 0.000 claims abstract description 98
- 239000004642 Polyimide Substances 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 8
- 125000006157 aromatic diamine group Chemical group 0.000 claims abstract 3
- 239000000758 substrate Substances 0.000 claims description 115
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- 239000000010 aprotic solvent Substances 0.000 claims description 23
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 4
- 239000013039 cover film Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 21
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 15
- 125000006158 tetracarboxylic acid group Chemical group 0.000 abstract description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 abstract description 3
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
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- 125000001072 heteroaryl group Chemical group 0.000 description 6
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- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 6
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
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- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 4
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 4
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical class [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 4
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
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- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 3
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- IFHGSECJTKJJIJ-UHFFFAOYSA-N [5-(trifluoromethylsulfonyloxy)naphthalen-1-yl] trifluoromethanesulfonate Chemical compound C1=CC=C2C(OS(=O)(=O)C(F)(F)F)=CC=CC2=C1OS(=O)(=O)C(F)(F)F IFHGSECJTKJJIJ-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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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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Abstract
Description
本出願は、参照によりその全体が本明細書に組み込まれる2018年8月7日出願の米国仮特許出願第62/715,422号明細書の利益を主張するものである。
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30〜100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0〜4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)。
後述の実施形態の詳細を扱う前に、いくつかの用語について定義又は明確化する。
α=(ΔL/L0)/ΔT
本明細書に開示される測定されたCTE値は、第1又は第2の加熱スキャン中に既知の方法により作成される。材料の相対膨張/収縮特性についての理解は、電子デバイスの作製及び/又は信頼性における重要な検討すべき事項である可能性がある。
本明細書に記載のポリアミド酸は、式I
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30〜100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0〜4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)の繰り返し単位を有する。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0〜4の整数であり、
c及びdは、同一であり又は異なり、1又は2である)。
ODPA//Bis−P/22TFMB 100//90/10。
(a)ジアミン成分及び二無水物成分が事前に一緒に混合され、次いで混合物が撹拌されている間に溶媒に少しずつ添加される方法。
(b)溶媒がジアミン成分及び二無水物成分の撹拌混合物に添加される方法。(上記の(a)とは反対に)
(c)ジアミンが溶媒に排他的に溶解され、次いで反応速度を制御することを可能にするような比で二無水物がそれに添加される方法。
(d)二無水物成分が溶媒に排他的に溶解され、次いで反応速度を制御することを可能にするような比でアミン成分がそれに添加される方法。
(e)ジアミン成分及び二無水物成分が溶媒に別個に溶解され、次いでこれらの溶液が反応器内で混合される方法。
(f)過剰なアミン成分を含むポリアミド酸及び過剰な二無水物成分を含む別のポリアミド酸が事前に形成され、次いで特にノンランダムコポリマー又はブロックコポリマーを作成できるような方法にて反応器内で相互に反応される方法。
(g)アミン成分及び二無水物成分の特定部分が最初に反応され、次いで残留ジアミン成分が反応される又はその逆である方法。
(h)成分が部分的に又は全体として任意の順序で溶媒の一部又は全部のいずれかに添加され、更に任意の成分の一部又は全部が溶媒の一部又は全部の溶液として添加され得る方法。
(i)二無水物成分の1つをジアミン成分の1つと最初に反応させて第1のポリアミド酸を生じさせる方法。次いで、他方の二無水物成分を他方のアミン成分と反応させると、第2のポリアミド酸が生じる。次いで、フィルム形成の前に、いくつかの方法のいずれか1つでポリアミド酸を組み合わせる。
式IVの繰り返し単位構造を有するポリイミドが提供される。
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30〜100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0〜4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)。
一般的に、ポリイミドフィルムは、化学又は熱変換によってポリイミド前駆体から調製することができる。一部の実施形態では、フィルムは、化学又は熱変換プロセスによって、対応するポリアミド酸溶液から調製される。本明細書に開示されるポリイミドフィルムは、特に電子デバイスにおけるガラスの柔軟な代替物として使用される場合、熱変換プロセスによって調製される。
本明細書に開示されたポリイミドフィルムは、例えば、OLED及びLCDディスプレイ等の電子ディスプレイデバイス内のいくつかの層で使用するために好適であり得る。このような層の非限定的な例としては、デバイス基板、タッチパネル、カラーフィルターシート用基板、カバーフィルムなどが挙げられる。各用途のための特定の材料の特性要件は、固有であり、本明細書に開示されたポリイミドフィルムのための適切な組成及び加工条件によって対応することができる。
この実施例は、式III、具体的には式IIIA−1を有するジアミン:4,4’−(ナフタレン−2,6−ジイル)ビス(3−(トリフルオロメチル)アニリン)、化合物1の調製を示している。
この実施例は、式Iを有するポリアミド酸を含む液体組成物の調製を示す。ポリアミド酸は、組成物BPDA/PMDA//化合物1 97/3//100を有した。
この実施例は、式IVを有するポリイミドフィルムの調製を示している。
引張り弾性率=10.9GPa
破断伸び=23.4%
CTE(第1の測定)=3.4ppm/℃
CTE(第2の測定)=1.4ppm/℃
492.6℃で1.0%のTGA重量損失
450nmでの透過率=61%
550nmでの透過率=79%
750nmでの透過率=85%
この実施例は、式III、具体的には式IIIB−1を有するジアミン:4,4’−(ナフタレン−1,5−ジイル)ビス(3−(トリフルオロメチル)アニリン)、化合物17の調製を示している。
機械式攪拌機、内部温度計、及び窒素バブラーを備えた20Lの4口丸底フラスコに、室温で、ジクロロメタン(10000mL)におけるナフタレン−1,5−ジオール(500g、3124.0ミリモル)とピリジン(1259mL、15620.0ミリモル)を入れた。トリフルオロメタンスルホン酸無水物(1320mL、7810.0ミリモル)を5〜10℃で4時間かけて滴下した。トリフルオロメタンスルホン酸無水物の添加が完了した後、反応混合物を室温で撹拌した。16時間後、反応混合物を10〜15℃で水(5000mL)に注ぎ、30分間撹拌した。有機層を分離し、水層をジクロロメタン(2×5000mL)で抽出した。合わせた有機相を1N HCl(7500mL)及び水(5000mL)で洗浄し、無水硫酸ナトリウム(Na2SO4)で乾燥させ、濾過し、減圧下で濃縮した。エタノール(2500mL)を粗固体に加え、室温で30分間撹拌した。固体材料を室温で濾過することにより収集し、真空下で乾燥させて、ナフタレン−1,5−ジイルビス(トリフルオロメタンスルホネート)(1190g、90%)を灰色の固体として得た。1H NMR(400MHz,CDCl3)δ:8.15(d,J=8.8Hz,2H),7.69(t,J=7.6Hz,2H),7.61(dd,J=0.8Hz及び7.6Hz,2H);UPLC:99.24%の純度。
機械式攪拌機、凝縮器、内部温度計、及び窒素バブラーを備えた20Lの4口丸底フラスコに、室温で、1,4−ジオキサン(5470mL)におけるナフタレン−1,5−ジイルビス(トリフルオロメタンスルホネート)(547.0g、1290.2ミリモル)、ビス(ピナコラート)ジボロン(721.0g、2838.5ミリモル)及び酢酸カリウム(760g、7741.5ミリモル)を入れた。反応混合物をアルゴンで15分間パージし、次いでPdCl2(dppf).DCM(53g、64.5ミリモル)を反応混合物に加え、アルゴンで再び10分間パージした。反応混合物を90〜95℃に加熱した。4時間後、反応混合物を室温に冷却し、セライト(登録商標)の床(bed)を通して濾過し、床をジクロロメタン(2500mL)で洗浄した。合わせた濾液を無水硫酸ナトリウムで乾燥させ、濾過し、減圧下で濃縮して、黒色の固体を得た。エタノール(2188mL)を固体に加え、室温で30分間撹拌した。固体材料を濾過により収集し、真空下で乾燥させて、1,5−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ナフタレン(402g、82%)を灰色の固体として得た。1H NMR(400MHz,CDCl3)δ:8.89(dd,J=1.2Hz及び8.0Hz,2H),8.07(dd,J=1.2Hz及び6.8Hz,2H),7.53(dd,J=6.8Hz及び8.4Hz,2H),1.42(s,24H);UPLC:97.95%の純度。
機械式攪拌機、内部温度計、及び窒素バブラーを備えた3Lの4口丸底フラスコに、トルエン(800mL)における1,5−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ナフタレン(40.0g、105.2ミリモル)、4−ブロモ−3−(トリフルオロメチル)アニリン(63.1g、263.4ミリモル)、2M炭酸ナトリウム水溶液(480mL)及びAliquat−336(4mL)を入れた。反応混合物をアルゴンで15分間パージし、次いでテトラキス(トリフェニルホスフィン)パラジウム(0)(12.1g、10.5ミリモル)を加え、アルゴンのパージを更に10分間続けた。反応混合物を110〜120℃に加熱した。16時間後、反応混合物を室温に冷却し、トルエン(650mL)で希釈し、セライト(登録商標)の床を通して濾過し、床をトルエン(100mL)で洗浄した。有機層を分離し、水(250mL)及びブライン(100mL)で洗浄し、無水硫酸ナトリウムで乾燥し、濾過し、減圧下で濃縮して、粗残留物を得た。粗残留物をシリカゲルカラムクロマトグラフィー(溶離液として10〜15%酢酸エチル/ヘキサン)で精製し、その後エタノール−クロロホルム(1:9)を使用して共沈させて固体を得た。固体を1,4−ジオキサン(200mL)に溶解し、
1,4−ジオキサン(100mL)における4N HClを0〜5℃で加え、室温で1時間撹拌を続けた。得られた固体を濾過により収集し、エタノール−酢酸エチル(3:7)で洗浄し、真空下で乾燥させて塩酸塩を得た。5%KOH溶液(210mL)を酢酸エチル(500mL)における塩に0〜5℃で加え、室温で1時間撹拌を続けた。酢酸エチル層を分離し、水とブラインで洗浄し、無水硫酸ナトリウムで乾燥し、濾過し、減圧下で濃縮して、4,4’−(ナフタレン−1,5)−ジイル)ビス(3−(トリフルオロメチル)アニリン)(15.87g、34%)をオフホワイトの固体として得た。融点:270〜273℃、FT−IR:1258.50cm-1(C−F)、 1H NMR(400MHz,CDCl3)δ:7.45(d,J=7.6Hz,2H),7.37−7.30(m,4H),7.20(d,J=8.4Hz,2H),7.12(d,J=2.4Hz,2H),6.92(dd,J=2.4Hz及び8.0Hz,2H),3.94(s,4H);19F NMR(376MHz,CDCl3)δ:−58.78;GCMS:446.2 [M]+ ;UPLC:2つのアトロプ異性体の混合物として99.95%の純度。
Claims (9)
- (a)式I
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30〜100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0〜4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)の繰り返し単位構造を有するポリアミド酸と、
(b)高沸点非プロトン性溶媒と、
を含む、液体組成物。 - 請求項4に記載の、式IVの繰り返し単位を含む、ポリイミドフィルム。
- 請求項4に記載の、式IVの繰り返し単位を有する、ポリイミドフィルムを含む少なくとも1つの層を有する、有機電子デバイス。
- 前記層は、デバイス基板、カラーフィルターシート用基板、カバーフィルム、及びタッチスクリーンパネルからなる群から選択されるデバイス構成要素において使用される、請求項8に記載の電子デバイス。
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