JP6368955B2 - 液晶配向処理剤、液晶配向膜および液晶表示素子 - Google Patents
液晶配向処理剤、液晶配向膜および液晶表示素子 Download PDFInfo
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- JP6368955B2 JP6368955B2 JP2015502996A JP2015502996A JP6368955B2 JP 6368955 B2 JP6368955 B2 JP 6368955B2 JP 2015502996 A JP2015502996 A JP 2015502996A JP 2015502996 A JP2015502996 A JP 2015502996A JP 6368955 B2 JP6368955 B2 JP 6368955B2
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 389
- 239000003795 chemical substances by application Substances 0.000 title claims description 136
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- -1 diamine compound Chemical class 0.000 claims description 110
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- 239000004642 Polyimide Substances 0.000 claims description 107
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- 229920000642 polymer Polymers 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 57
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- 229910052731 fluorine Inorganic materials 0.000 claims description 43
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- 239000002243 precursor Substances 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 34
- 239000011737 fluorine Substances 0.000 claims description 34
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 33
- 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 31
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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- 125000001424 substituent group Chemical group 0.000 description 7
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- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 5
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- 125000003277 amino group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 5
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- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
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- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 3
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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
- C08G73/1075—Partially aromatic polyimides
- C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
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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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on 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 C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Liquid Crystal (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
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| JP7161147B2 (ja) * | 2017-06-14 | 2022-10-26 | 日産化学株式会社 | 液晶配向剤、液晶配向膜及びそれを用いた液晶表示素子並びに該液晶配向膜の製造方法 |
| WO2019013339A1 (ja) * | 2017-07-14 | 2019-01-17 | 日産化学株式会社 | 液晶配向剤、液晶配向膜及びそれを用いた液晶表示素子 |
| JP7256472B2 (ja) * | 2017-10-25 | 2023-04-12 | 日産化学株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| CN112005164B (zh) * | 2018-03-30 | 2023-09-12 | 日产化学株式会社 | 液晶取向剂、液晶取向膜和液晶表示元件 |
| JP7317939B2 (ja) * | 2019-03-07 | 2023-07-31 | 富士フイルム株式会社 | 偏光素子および画像表示装置 |
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| KR101115058B1 (ko) * | 2008-07-09 | 2012-02-13 | 주식회사 엘지화학 | 폴리이미드-폴리아믹산 공중합체, 이의 제조방법, 이를포함하는 감광성 조성물 및 이에 의해 제공된 보호막 |
| JP5884258B2 (ja) * | 2009-09-18 | 2016-03-15 | Jnc株式会社 | 液晶配向剤、液晶配向膜、液晶配向膜の製造方法および液晶表示素子 |
| KR101734600B1 (ko) * | 2009-11-09 | 2017-05-11 | 제이엔씨 주식회사 | 액정 표시 소자, 액정 조성물 및 배향제 그리고 액정 표시 소자의 제조방법 |
| CN103119509B (zh) * | 2010-07-26 | 2015-08-19 | 日产化学工业株式会社 | 液晶取向处理剂、液晶取向膜及液晶显示元件 |
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| TW201500462A (zh) | 2015-01-01 |
| JP2018087343A (ja) | 2018-06-07 |
| CN105164579A (zh) | 2015-12-16 |
| WO2014133042A1 (ja) | 2014-09-04 |
| JP6504377B2 (ja) | 2019-04-24 |
| KR102184058B1 (ko) | 2020-11-27 |
| JPWO2014133042A1 (ja) | 2017-02-02 |
| KR20150122210A (ko) | 2015-10-30 |
| TWI620791B (zh) | 2018-04-11 |
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