JP5454754B2 - 液晶配向剤、液晶配向膜および液晶表示素子 - Google Patents
液晶配向剤、液晶配向膜および液晶表示素子 Download PDFInfo
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- JP5454754B2 JP5454754B2 JP2008158051A JP2008158051A JP5454754B2 JP 5454754 B2 JP5454754 B2 JP 5454754B2 JP 2008158051 A JP2008158051 A JP 2008158051A JP 2008158051 A JP2008158051 A JP 2008158051A JP 5454754 B2 JP5454754 B2 JP 5454754B2
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- Prior art keywords
- liquid crystal
- polyamic acid
- aligning agent
- crystal aligning
- dianhydride
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 143
- 239000003795 chemical substances by application Substances 0.000 title claims description 53
- 229920005575 poly(amic acid) Polymers 0.000 claims description 65
- 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 46
- 229920000642 polymer Polymers 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000000962 organic group Chemical group 0.000 claims description 26
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 20
- 239000004642 Polyimide Substances 0.000 claims description 17
- 229920001721 polyimide Polymers 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 10
- RHRNYXVSZLSRRP-UHFFFAOYSA-N 3-(carboxymethyl)cyclopentane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CC1C(C(O)=O)CC(C(O)=O)C1C(O)=O RHRNYXVSZLSRRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 60
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 50
- -1 diamine compound Chemical class 0.000 description 37
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
- 239000000758 substrate Substances 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 230000018044 dehydration Effects 0.000 description 11
- 238000006297 dehydration reaction Methods 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000006358 imidation reaction Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
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- 238000006798 ring closing metathesis reaction Methods 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 6
- 239000003054 catalyst Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- DMFZUPUWYGUECI-UHFFFAOYSA-N 4-(2,5-dioxooxolan-3-yl)benzo[e][2]benzofuran-1,3-dione Chemical compound O=C1OC(=O)CC1C1=CC2=CC=CC=C2C2=C1C(=O)OC2=O DMFZUPUWYGUECI-UHFFFAOYSA-N 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
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- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
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- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
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- 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
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Mathematical Physics (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008158051A JP5454754B2 (ja) | 2007-07-23 | 2008-06-17 | 液晶配向剤、液晶配向膜および液晶表示素子 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007191127 | 2007-07-23 | ||
| JP2007191127 | 2007-07-23 | ||
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US10696901B2 (en) | 2015-11-11 | 2020-06-30 | Lg Chem, Ltd. | Method of manufacturing liquid crystal alignment layer, liquid crystal alignment layer manufactured by using the same, and liquid crystal display device |
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| JP4944217B2 (ja) | 2010-03-09 | 2012-05-30 | 株式会社 日立ディスプレイズ | 液晶表示装置 |
| EP3031864B1 (en) | 2013-08-06 | 2020-11-04 | Mitsubishi Gas Chemical Company, Inc. | Polyimide resin composition, and (polyimide resin)-fiber composite material |
| KR101856725B1 (ko) | 2016-05-13 | 2018-05-10 | 주식회사 엘지화학 | 액정 배향제 조성물, 액정 배향막의 제조 방법, 이를 이용한 액정 배향막 및 액정 표시소자 |
| KR102202056B1 (ko) | 2018-02-21 | 2021-01-11 | 주식회사 엘지화학 | 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 및 이를 이용한 액정 배향막 |
| KR20210005015A (ko) | 2018-04-27 | 2021-01-13 | 닛산 가가쿠 가부시키가이샤 | 액정 조광 소자 |
| JP6727282B2 (ja) * | 2018-12-26 | 2020-07-22 | 株式会社ジャパンディスプレイ | 液晶表示装置 |
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| JPS59142526A (ja) * | 1983-02-03 | 1984-08-15 | Sharp Corp | 液晶表示素子 |
| JPH0766125B2 (ja) * | 1986-09-02 | 1995-07-19 | キヤノン株式会社 | カイラルスメクチック液晶素子 |
| JP2621347B2 (ja) * | 1988-05-23 | 1997-06-18 | 日本合成ゴム株式会社 | 液晶表示素子用配向材 |
| DE69732949T2 (de) * | 1996-05-16 | 2006-02-23 | Jsr Corp. | Flüssigkristallausrichtungsmittel |
| JP2002040437A (ja) * | 2000-07-19 | 2002-02-06 | Matsushita Electric Ind Co Ltd | 液晶表示パネル |
| JP2002311437A (ja) * | 2001-04-12 | 2002-10-23 | Matsushita Electric Ind Co Ltd | 液晶表示パネル |
| JP4344935B2 (ja) * | 2004-06-16 | 2009-10-14 | Ｊｓｒ株式会社 | 液晶配向剤および液晶表示素子 |
| JP4434862B2 (ja) * | 2004-07-08 | 2010-03-17 | Ｊｓｒ株式会社 | 液晶配向剤および液晶表示素子 |
| JP5055727B2 (ja) * | 2004-11-01 | 2012-10-24 | Ｊｎｃ株式会社 | 液晶配向剤及び液晶表示素子 |
| KR101212135B1 (ko) * | 2005-06-14 | 2012-12-14 | 엘지디스플레이 주식회사 | 액정표시소자 및 그 제조방법 |
| JP2007086287A (ja) * | 2005-09-21 | 2007-04-05 | Jsr Corp | 液晶配向剤および液晶表示素子 |
| JP5041157B2 (ja) * | 2007-01-10 | 2012-10-03 | Ｊｓｒ株式会社 | 垂直配向型液晶配向剤および垂直配向型液晶表示素子 |
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| US10696901B2 (en) | 2015-11-11 | 2020-06-30 | Lg Chem, Ltd. | Method of manufacturing liquid crystal alignment layer, liquid crystal alignment layer manufactured by using the same, and liquid crystal display device |
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| Publication number | Publication date |
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| KR20090010899A (ko) | 2009-01-30 |
| CN101634778B (zh) | 2013-05-29 |
| TWI442145B (zh) | 2014-06-21 |
| CN101634778A (zh) | 2010-01-27 |
| KR101486083B1 (ko) | 2015-01-23 |
| TW200912485A (en) | 2009-03-16 |
| JP2009048174A (ja) | 2009-03-05 |
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