TWI485181B - A liquid crystal alignment agent and a liquid crystal display device using the same, and novel diamine - Google Patents
A liquid crystal alignment agent and a liquid crystal display device using the same, and novel diamine Download PDFInfo
- Publication number
- TWI485181B TWI485181B TW098120257A TW98120257A TWI485181B TW I485181 B TWI485181 B TW I485181B TW 098120257 A TW098120257 A TW 098120257A TW 98120257 A TW98120257 A TW 98120257A TW I485181 B TWI485181 B TW I485181B
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid crystal
- crystal alignment
- diamine
- polyimine
- formula
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 199
- 150000004985 diamines Chemical class 0.000 title claims description 116
- 239000003795 chemical substances by application Substances 0.000 title claims description 81
- 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 54
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 43
- 229920005575 poly(amic acid) Polymers 0.000 claims description 17
- 108010039918 Polylysine Proteins 0.000 claims description 15
- 229920000656 polylysine Polymers 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- -1 n-pentadecyl group Chemical group 0.000 description 38
- 210000002858 crystal cell Anatomy 0.000 description 37
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- 125000003118 aryl group Chemical group 0.000 description 4
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- 239000012535 impurity Substances 0.000 description 1
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- IPLONMMJNGTUAI-UHFFFAOYSA-M lithium;bromide;hydrate Chemical compound [Li+].O.[Br-] IPLONMMJNGTUAI-UHFFFAOYSA-M 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
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- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007430 reference method Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000002345 steroid group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/32—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and esterified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008158456 | 2008-06-17 |
Publications (2)
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|---|---|
| TW201005007A TW201005007A (en) | 2010-02-01 |
| TWI485181B true TWI485181B (zh) | 2015-05-21 |
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| TW098120257A TWI485181B (zh) | 2008-06-17 | 2009-06-17 | A liquid crystal alignment agent and a liquid crystal display device using the same, and novel diamine |
| TW103119539A TWI510455B (zh) | 2008-06-17 | 2009-06-17 | A liquid crystal alignment agent and a liquid crystal display device using the same, and novel diamine |
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| TW103119539A TWI510455B (zh) | 2008-06-17 | 2009-06-17 | A liquid crystal alignment agent and a liquid crystal display device using the same, and novel diamine |
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| JP (2) | JP5594136B2 (ja) |
| KR (2) | KR101616143B1 (ja) |
| CN (1) | CN102067024B (ja) |
| TW (2) | TWI485181B (ja) |
| WO (1) | WO2009154208A1 (ja) |
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| TWI810473B (zh) * | 2019-07-30 | 2023-08-01 | 日商Ｔｍｔ機械股份有限公司 | 合成纖維紗用接線系統 |
| TWI810472B (zh) * | 2019-07-30 | 2023-08-01 | 日商Ｔｍｔ機械股份有限公司 | 合成纖維紗用接線系統 |
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| CN102893207B (zh) * | 2010-03-15 | 2015-05-20 | 日产化学工业株式会社 | 聚酰胺酸酯液晶取向剂和使用其的液晶取向膜 |
| JP5904119B2 (ja) | 2010-03-15 | 2016-04-13 | 日産化学工業株式会社 | 末端を修飾したポリアミック酸エステルを含有する液晶配向剤、及び液晶配向膜 |
| JPWO2011115079A1 (ja) * | 2010-03-15 | 2013-06-27 | 日産化学工業株式会社 | 光配向処理法用の液晶配向剤、及びそれを用いた液晶配向膜 |
| CN102893209B (zh) | 2010-03-15 | 2015-05-06 | 日产化学工业株式会社 | 含有聚酰胺酸酯的液晶取向剂和液晶取向膜 |
| KR101824279B1 (ko) | 2010-06-30 | 2018-01-31 | 닛산 가가쿠 고교 가부시키 가이샤 | 액정 배향 처리제, 액정 배향막 및 그것을 사용한 액정 표시 소자 |
| WO2012008464A1 (ja) | 2010-07-13 | 2012-01-19 | 日産化学工業株式会社 | 液晶配向処理剤、液晶配向膜及び液晶表示素子 |
| JP5904121B2 (ja) | 2010-07-26 | 2016-04-13 | 日産化学工業株式会社 | 液晶配向処理剤、液晶配向膜及び液晶表示素子 |
| JP5900344B2 (ja) * | 2010-10-19 | 2016-04-06 | 日産化学工業株式会社 | 光配向処理法に適した液晶配向剤、及びそれを用いた液晶配向膜 |
| TWI427104B (zh) * | 2010-10-26 | 2014-02-21 | Chi Mei Corp | 液晶配向劑，液晶配向膜，及含有該液晶配向膜的液晶顯示元件 |
| CN103282824B (zh) * | 2010-10-28 | 2016-01-13 | 日产化学工业株式会社 | 液晶取向剂及液晶取向膜 |
| TWI398291B (zh) * | 2010-12-13 | 2013-06-11 | Ind Tech Res Inst | 配向溶液之純化方法及純化裝置 |
| TWI515260B (zh) * | 2011-01-28 | 2016-01-01 | Nissan Chemical Ind Ltd | A liquid crystal aligning agent containing polyacidic acid and polyamic acid |
| WO2012157983A2 (ko) * | 2011-05-18 | 2012-11-22 | 주식회사 동진쎄미켐 | 아민 화합물, 이의 제조방법, 액정 배향제, 액정 배향막 및 액정 표시 소자 |
| CN104203970B (zh) * | 2012-01-12 | 2016-08-17 | 和光纯药工业株式会社 | 液晶取向剂 |
| CN104220488B (zh) * | 2012-02-01 | 2017-05-31 | 日产化学工业株式会社 | 新型二胺、聚合物、液晶取向剂、液晶取向膜以及使用其的液晶显示元件 |
| US20150056367A1 (en) * | 2012-03-16 | 2015-02-26 | Soki Corporation | Composition for forming liquid crystal alignment film and liquid crystal display element |
| JP6299977B2 (ja) * | 2012-12-12 | 2018-03-28 | 日産化学工業株式会社 | 液晶配向処理剤、液晶配向膜および液晶表示素子 |
| KR102221553B1 (ko) * | 2014-05-09 | 2021-03-02 | 삼성디스플레이 주식회사 | 3차원 표시 장치 및 이를 위한 액정 렌즈 패널 장치 |
| WO2018058343A1 (en) * | 2016-09-28 | 2018-04-05 | Dow Global Technologies Llc | Dmpa-based solvent systems for the synthesis of poly(amic acid) and polyimide polymers |
| TWI902144B (zh) * | 2024-02-17 | 2025-10-21 | 奇美實業股份有限公司 | 光配向法用的液晶配向劑、液晶配向膜與液晶顯示元件 |
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| JP2001011177A (ja) * | 1999-06-28 | 2001-01-16 | Kanegafuchi Chem Ind Co Ltd | 新規ポリイミド組成物およびこれに使用される新規酸二無水物 |
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| US4124593A (en) * | 1975-11-13 | 1978-11-07 | Ciba-Geigy Corporation | Aromatic dicarboximides |
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| GB9419203D0 (en) * | 1994-09-23 | 1994-11-09 | Nycomed Innovation Ab | Contrast media |
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| ATE410161T1 (de) * | 2003-05-02 | 2008-10-15 | Elan Pharm Inc | 4-bromo-5-(2-chloro-benzoylamino)-1h-pyrazol-3- carbonsäureamid-derivate und verwandte verbindungen als bradykinin b1 rezeptor antagonisten zur behandlung von entzündlichen erkrankungen |
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| KR100822499B1 (ko) * | 2005-12-01 | 2008-04-16 | 주식회사 엘지화학 | 신규한 폴리이미드 및 이의 제조방법 |
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| JP2008176304A (ja) * | 2006-12-22 | 2008-07-31 | Jsr Corp | 液晶配向剤、液晶配向膜、液晶表示素子および光学部材 |
| JP4544432B2 (ja) * | 2007-02-21 | 2010-09-15 | Ｊｓｒ株式会社 | シンナモイル基を持つジアミン化合物の製造法 |
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2009
- 2009-06-16 KR KR1020117000395A patent/KR101616143B1/ko active Active
- 2009-06-16 JP JP2010517930A patent/JP5594136B2/ja active Active
- 2009-06-16 WO PCT/JP2009/060964 patent/WO2009154208A1/ja not_active Ceased
- 2009-06-16 KR KR1020157025673A patent/KR101704332B1/ko active Active
- 2009-06-16 CN CN200980123423.XA patent/CN102067024B/zh active Active
- 2009-06-17 TW TW098120257A patent/TWI485181B/zh active
- 2009-06-17 TW TW103119539A patent/TWI510455B/zh active
-
2013
- 2013-12-13 JP JP2013258610A patent/JP5729458B2/ja active Active
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| JPS57120553A (en) * | 1981-01-21 | 1982-07-27 | Hitachi Ltd | Preparation of aromatic amine compound |
| JP2001011177A (ja) * | 1999-06-28 | 2001-01-16 | Kanegafuchi Chem Ind Co Ltd | 新規ポリイミド組成物およびこれに使用される新規酸二無水物 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI810473B (zh) * | 2019-07-30 | 2023-08-01 | 日商Ｔｍｔ機械股份有限公司 | 合成纖維紗用接線系統 |
| TWI810472B (zh) * | 2019-07-30 | 2023-08-01 | 日商Ｔｍｔ機械股份有限公司 | 合成纖維紗用接線系統 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5594136B2 (ja) | 2014-09-24 |
| KR101704332B1 (ko) | 2017-02-07 |
| TWI510455B (zh) | 2015-12-01 |
| KR20150111376A (ko) | 2015-10-05 |
| CN102067024A (zh) | 2011-05-18 |
| KR20110017908A (ko) | 2011-02-22 |
| TW201005007A (en) | 2010-02-01 |
| JPWO2009154208A1 (ja) | 2011-12-01 |
| JP2014097986A (ja) | 2014-05-29 |
| WO2009154208A1 (ja) | 2009-12-23 |
| CN102067024B (zh) | 2013-08-07 |
| TW201434803A (zh) | 2014-09-16 |
| JP5729458B2 (ja) | 2015-06-03 |
| KR101616143B1 (ko) | 2016-04-27 |
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