JP2021521284A - 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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- JP2021521284A JP2021521284A JP2020554833A JP2020554833A JP2021521284A JP 2021521284 A JP2021521284 A JP 2021521284A JP 2020554833 A JP2020554833 A JP 2020554833A JP 2020554833 A JP2020554833 A JP 2020554833A JP 2021521284 A JP2021521284 A JP 2021521284A
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- aryl
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- 229920000642 polymer Polymers 0.000 title description 30
- 229920001721 polyimide Polymers 0.000 claims abstract description 119
- -1 cyano, hydroxyl Chemical group 0.000 claims abstract description 60
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 50
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 44
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 43
- 239000004642 Polyimide Substances 0.000 claims abstract description 39
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 33
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims abstract description 24
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 17
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 125000004405 heteroalkoxy group Chemical group 0.000 claims abstract description 14
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract 9
- 125000006157 aromatic diamine group Chemical group 0.000 claims abstract 3
- 239000000758 substrate Substances 0.000 claims description 110
- 229920005575 poly(amic acid) Polymers 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 59
- 239000010408 film Substances 0.000 claims description 47
- 239000007788 liquid Substances 0.000 claims description 43
- 238000009835 boiling Methods 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 239000000010 aprotic solvent Substances 0.000 claims description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 229910052705 radium Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000013039 cover film Substances 0.000 claims description 2
- 125000005750 substituted cyclic group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 21
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 238000000034 method Methods 0.000 description 256
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- 239000010410 layer Substances 0.000 description 128
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- 239000003054 catalyst Substances 0.000 description 25
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 24
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 24
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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 description 18
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- 239000011248 coating agent Substances 0.000 description 17
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- 229910052794 bromium Inorganic materials 0.000 description 10
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- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
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- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 229920002223 polystyrene Polymers 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 8
- 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 7
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 230000004580 weight loss Effects 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000012286 potassium permanganate Substances 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 4
- 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
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-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
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 125000004104 aryloxy group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
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- 238000000151 deposition Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005401 electroluminescence Methods 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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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
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- MBZVPENZVICHRL-UHFFFAOYSA-N 2,3,6,7-tetramethyl-9,9-bis(trifluoromethyl)xanthene Chemical compound O1C2=CC(C)=C(C)C=C2C(C(F)(F)F)(C(F)(F)F)C2=C1C=C(C)C(C)=C2 MBZVPENZVICHRL-UHFFFAOYSA-N 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 3
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- 239000012299 nitrogen atmosphere Substances 0.000 description 3
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
Raは、1種以上の異なるテトラカルボン酸成分残基を表し、
Rbは、1種以上の異なる芳香族ジアミン残基又は芳香族ジイソシアネート残基を表し、
5〜100モル%のRaは、式II
R1は、H、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R2は、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R3及びR4は、同一又は異なり、アルキル、フルオロアルキル、及びシリルからなる群から選択され、
x及びyは、同一又は異なり、0〜2の整数であり、
*は結合点を示す)を有する]の繰り返し単位を有するポリアミド酸(polyamic acid)が提供される。
(a)式Iの繰り返し単位を有するポリアミド酸と、(b)少なくとも1種の高沸点非プロトン性溶媒とを含む組成物が更に提供される。
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
本明細書に記載のポリアミド酸は、式I
Raは、1つ以上の異なるテトラカルボン酸成分残基を表し、
Rbは、1つ以上の異なる芳香族ジアミン残基又は芳香族ジイソシアネート残基を表し、
5〜100モル%のRaは、式II
R1は、H、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R2は、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R3とR4は、同一又は異なり、アルキル、フルオロアルキル、及びシリルからなる群から選択され、
x及びyは、同一又は異なり、0〜2の整数であり、
*は結合点を示す)を有する)の繰り返し単位構造を有する。
R1は、H、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R2は、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R3及びR4は、同一又は異なり、アルキル、フルオロアルキル、及びシリルからなる群から選択され、
x及びyは、同一又は異なり、0〜2の整数である)。
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、その後に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、その後に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、その後に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、その後に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、その後に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、その後に残留ジアミン成分が反応されるか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。その後に、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。その後に、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III
Rbは、1つ以上の異なる芳香族ジアミン残基又は芳香族ジイソシアネート残基を表し、
5〜100モル%のRaは、式II
R1は、H、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R2は、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R3及びR4は、同一又は異なり、アルキル、フルオロアルキル、及びシリルからなる群から選択され、
x及びyは、同一又は異なり、0〜2の整数であり、
*は結合点を示す)を有する)の繰り返し単位構造を有するポリイミドが提供される。
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、デバイス基材、タッチパネル、カラーフィルターシート用基材、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。
6FDA=4,4’−ヘキサフルオロイソ−プロピリデンビスフタル酸二無水物
BPDA=3,3’,4,4’−ビフェニルテトラカルボン酸二無水物
DA3MG=1,3−ビス(4−アミノフェノキシ)プロパン(DA3MG)
FDA=9,9’−ビス(4−アミノフェニル)フルオレン
PMDA=ピロメリット酸二無水物
TFMB=2,2’−ビス(トリフルオロメチル)ベンジジン
この実施例は、式II−Aを有する化合物、化合物3の調製を示す。
この実施例は、式II−Aを有する化合物、化合物18の調製を示す。
この実施例は、式II−Aを有する化合物、化合物19の調製を示す。
1L2口丸底フラスコに、9H−フルオレン−9−オン(36.04g、200ミリモル)、4,4’−オキシビス(1,2−ジメチルベンゼン)(63.92g、240ミリモル)及びメタンスルホン酸(52mL、800ミリモル)を入れた。反応物を窒素雰囲気下145oCで加熱した。18時間後、反応物を室温に冷却し、ジクロロメタン(550mL)を反応物に加えた。有機層を水(2×250mL)、炭酸ナトリウム(1M、250mL)水溶液及びブライン(250mL)で洗浄した。有機層を撹拌しながら室温で30分間MgSO4で乾燥させた。溶液の容量を約200mLに減らし、ヘキサン(100mL)を加えた。溶液を、塩基性アルミナ(2cm×8cm)及びシリカゲル(8cm×8cm)を充填した短いカラムに通し、ジクロロメタン:ヘキサン(1:1)で溶出した。UV光下で水色の輝度を有する生成物含有画分を収集し、溶媒を減圧下で濃縮した。粗生成物をジクロロメタン/アセトニトリルから再結晶化して、2’,3’,6’,7’−テトラメチル−スピロ[9H−フルオレン−9,9’−[9H]キサンテン](36.5g)を白色の結晶性物質として得た。1H NMR(500MHz,CD2Cl2)δ:7.85(d,J=10.0Hz,2H),7.40(t,J=7.5Hz,2H),7.23(t,J=7.5Hz,2H),7.11(d,J=10.0Hz,2H),7.02(s,2H),6.10(s,2H),2.23(2,6H),1.93(s,6H);HPLC:98.22%の純度。
この実施例は、化合物2を使用した、式Iを有するポリアミド酸PAA−7の調製を示している。PAA−7の組成は、NMPにおけるBPDA/化合物2/6FDA//TFMB20/50/30//100である。窒素流入口及び流出口、メカニカルスターラー及び熱電対を備えた500mL反応フラスコに、22.42gのTFMB(0.07モル)と250.31gの1−メチル−2−ピロリドン(NMP)を入れた。混合物を窒素雰囲気下、室温で約30分間攪拌した。その後、4.12g(0.014モル)のBPDAをジアミンの撹拌溶液に少しずつゆっくりと加え、続いて14.15g(0.035モル)の化合物2及び8.40g(0.019モル)の6FDAを少しずつ加えた。最大反応温度を30℃未満に保つために、二無水物の添加速度を制御した。二無水物の添加が終了した後、更なる27.81gのNMPを使用して、容器及び反応フラスコの壁から残留している二無水物粉末を洗い流した。得られた混合物を7日間撹拌した。別個に、NMP中の6FDAの5%溶液を調製し、ポリマーの分子量及びポリマー溶液の粘度を増加させるために経時的に少量(約3.1g)ずつ添加した。ブルックフィールドコーンプレート型粘度計を使用して、試験のため反応フラスコから少量の試料を除去することによって溶液粘度を監視した。合計13.99gのこの仕上げ溶液を加えた(0.697g、0.00157モル6FDA)。反応は、ポリマー平衡化を可能にするために室温にて穏やかな攪拌下で一晩進行させた。ポリマー溶液の最終粘度は、25℃で11,600cpsであった。
これらの実施例は、式IIIを有するポリイミドフィルムの調製及び特性を示している。
これらの実施例は、式IIIを有するポリイミドフィルムの調製及び特性を示している。
これらの実施例は、式IIIを有するポリイミドフィルムの調製及び特性を示している。
Claims (10)
- (a)式I
Raは、1種以上の異なるテトラカルボン酸成分残基を表し、
Rbは、1種以上の異なる芳香族ジアミン残基又は芳香族ジイソシアネート残基を表し、
5〜100モル%のRaは、式II
R1は、H、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R2は、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R3及びR4は、同じ又は異なり、アルキル、フルオロアルキル、及びシリルからなる群から選択され、
x及びyは同じ又は異なり、0〜2の整数であり、
*は結合点を示す)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)少なくとも1種の高沸点非プロトン性溶媒と、を含む液体組成物。 - R1及びR2の少なくとも1つは、フッ素化基である、請求項1に記載の液体組成物。
- R1及びR2の少なくとも1つは、非置換又は置換炭化水素アリールである、請求項1に記載の液体組成物。
- R1及びR2は、一緒に結合して、シクロアルキル基、炭化水素アリール基、及びヘテロアリール基からなる群から選択される非置換又は置換環状基を形成する、請求項1に記載の液体組成物。
- 40〜60モル%のRaは、式IIを有する、請求項1に記載の液体組成物。
- 式III
Rbは、1種以上の異なる芳香族ジアミン残基又は芳香族ジイソシアネート残基を表し、
5〜100モル%のRaは、式II
R1は、H、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R2は、ハロゲン、シアノ、ヒドロキシル、アルキル、ヘテロアルキル、アルコキシ、ヘテロアルコキシ、フルオロアルキル、シリル、炭化水素アリール、置換炭化水素アリール、ヘテロアリール、置換ヘテロアリール、ビニル、及びアリルからなる群から選択され、
R3及びR4は、同じ又は異なり、アルキル、フルオロアルキル、及びシリルからなる群から選択され、
x及びyは同じ又は異なり、0〜2の整数であり、
*は結合点を示す)を有する]の繰り返し単位構造を有するポリイミド。 - 前記フィルムは、350℃超のTg及び20ppm/℃未満のCTEを有する、請求項6に記載のポリイミドフィルム。
- 前記フィルムは、350℃超のTg及び100未満の光遅延を有する、請求項6に記載のポリイミドフィルム。
- 前記フィルムは、350℃超のTg、250nm未満の光遅延、及び5.0未満のb*値を有する、請求項6に記載のポリイミドフィルム。
- 電子デバイスであって、
請求項6に記載の式IIIの繰り返し単位を有するポリイミドフィルムは、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使用される、電子デバイス。
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WO2023157790A1 (ja) * | 2022-02-16 | 2023-08-24 | 株式会社カネカ | ポリアミド酸、ポリアミド酸組成物、ポリイミド、ポリイミド膜、積層体、積層体の製造方法及び電子デバイス |
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- 2019-04-01 CN CN201980037989.4A patent/CN112424261A/zh active Pending
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WO2019195148A1 (en) | 2019-10-10 |
CN112424261A (zh) | 2021-02-26 |
US20210017335A1 (en) | 2021-01-21 |
KR20200129166A (ko) | 2020-11-17 |
TW201943798A (zh) | 2019-11-16 |
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