JPH01180518A - Orientation treating agent - Google Patents
Orientation treating agentInfo
- Publication number
- JPH01180518A JPH01180518A JP436588A JP436588A JPH01180518A JP H01180518 A JPH01180518 A JP H01180518A JP 436588 A JP436588 A JP 436588A JP 436588 A JP436588 A JP 436588A JP H01180518 A JPH01180518 A JP H01180518A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- monoamine
- polyimide resin
- diamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 229920001721 polyimide Polymers 0.000 claims abstract description 21
- 239000009719 polyimide resin Substances 0.000 claims abstract description 20
- 150000004985 diamines Chemical class 0.000 claims abstract description 17
- 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 abstract description 16
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 36
- 210000002858 crystal cell Anatomy 0.000 abstract description 21
- 239000004642 Polyimide Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 17
- 239000000758 substrate Substances 0.000 description 12
- 229920005575 poly(amic acid) Polymers 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- -1 tetracarboxylic Acid dianhydride Chemical class 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- OVEMTTZEBOCJDV-UHFFFAOYSA-N 4-hexylaniline Chemical compound CCCCCCC1=CC=C(N)C=C1 OVEMTTZEBOCJDV-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 1
- DHIKMHDCNWDZSS-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dibromophenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dibromophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=C(Br)C=C(C(C=2C=C(Br)C(OC=3C=CC(N)=CC=3)=C(Br)C=2)(C(F)(F)F)C(F)(F)F)C=C1Br DHIKMHDCNWDZSS-UHFFFAOYSA-N 0.000 description 1
- VXMYUOSDIMLATO-UHFFFAOYSA-N 4-dodecoxyaniline Chemical compound CCCCCCCCCCCCOC1=CC=C(N)C=C1 VXMYUOSDIMLATO-UHFFFAOYSA-N 0.000 description 1
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 description 1
- DETPMDIIFZGDAE-UHFFFAOYSA-N 4-hexadecoxyaniline Chemical compound CCCCCCCCCCCCCCCCOC1=CC=C(N)C=C1 DETPMDIIFZGDAE-UHFFFAOYSA-N 0.000 description 1
- ACYGZCHBIGKPGR-UHFFFAOYSA-N 4-octoxyaniline Chemical compound CCCCCCCCOC1=CC=C(N)C=C1 ACYGZCHBIGKPGR-UHFFFAOYSA-N 0.000 description 1
- ORKQJTBYQZITLA-UHFFFAOYSA-N 4-octylaniline Chemical compound CCCCCCCCC1=CC=C(N)C=C1 ORKQJTBYQZITLA-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Abstract
Description
【発明の詳細な説明】
（イ）産業上の利用分野
本発明は液晶セル用配向処理剤に関するものであり、更
に詳しくは液晶分子が基板に対し高められた傾斜配向角
を有する液晶セル用配向処理剤に関するものである。Detailed Description of the Invention (a) Industrial Application Field The present invention relates to an alignment treatment agent for liquid crystal cells, and more specifically, an alignment treatment agent for liquid crystal cells in which liquid crystal molecules have a tilted alignment angle with respect to a substrate. This relates to processing agents.
（ロ）従来の技術
ネマティック液晶分子を透明電極の付いたガラス或いは
プラスチックフィルム等の透明基板にほぼ平行に配向さ
せるための基板処理剤としては、従来よりポリイミド樹
脂膜をはじめとする有機樹脂膜が最も一般的に使用され
ている。(b) Conventional technology Organic resin films such as polyimide resin films have conventionally been used as substrate processing agents for aligning nematic liquid crystal molecules almost parallel to a transparent substrate such as glass or plastic film with transparent electrodes. Most commonly used.
この場合、基板上に形成された有機樹脂膜を布で一定の
方向ヘラピングすることにより、ラビング方向へ液晶分
子が配向し、同時に基板表面に対して通常１〜３°程度
の液晶傾斜配向角を生ずることが知られている。In this case, by rubbing the organic resin film formed on the substrate in a certain direction with a cloth, the liquid crystal molecules are aligned in the rubbing direction, and at the same time, the liquid crystal tilt orientation angle is usually about 1 to 3 degrees with respect to the substrate surface. known to occur.
又、液晶分子を大きく傾斜配向させる方法として、従来
から酸化硅素等の無機膜を基板上に医者する方法等が行
われている。Furthermore, as a method for aligning liquid crystal molecules with a large inclination, a method has been conventionally used in which an inorganic film of silicon oxide or the like is deposited on a substrate.
（ハ）発明が解決しようとする問題点
基板上に形成された有機樹脂膜をラビングする方法では
、液晶分子を大きく傾斜配向することは困難である。(c) Problems to be Solved by the Invention With the method of rubbing an organic resin film formed on a substrate, it is difficult to align liquid crystal molecules with a large tilt.
又、基板上に無機膜を蒸着する方法は、ラビング法に比
べ繁雑であり実際の工業的生産においては必ずしも適切
な方法ではない。Furthermore, the method of depositing an inorganic film on a substrate is more complicated than the rubbing method, and is not necessarily an appropriate method for actual industrial production.
（ニ）問題点を解決するための手段
本発明者らは、上記問題点を解決すべく鋭意検討を進め
、既に特開昭６２−２９７８１９号において、ジアミン
、テトラカルボン酸２無水物及び長鎖アルキル基を有す
るモノアミンを所定の割合で反応、重合させて得られる
ポリイミド樹脂を液晶セル用配向処理剤として用いるこ
とを提案した。(d) Means for Solving the Problems The present inventors have conducted intensive studies to solve the above problems, and have already published a study on diamines, tetracarboxylic dianhydrides and long chain We proposed the use of a polyimide resin obtained by reacting and polymerizing monoamines having alkyl groups at a predetermined ratio as an alignment treatment agent for liquid crystal cells.
本発明者らは、ジアミン成分としてパーフルオロアルキ
ル基を含むジアミンを用いることにより液晶分子を更に
大きく傾斜配向させ、且つ均一塗布性に優れた液晶セル
用配向処理剤が得られることを見出し、本発明を完成す
るに至った。The present inventors have discovered that by using a diamine containing a perfluoroalkyl group as a diamine component, it is possible to obtain an alignment treatment agent for liquid crystal cells that allows liquid crystal molecules to be more tiltedly aligned and has excellent uniform coating properties, and has developed the present invention. The invention was completed.
即ち、本発明は一般式（１）で表される（式中、Ｒ１及
びＲｇは互いに同−又は異る炭素数１〜６のパーフルオ
ロアルキルｉ、Ｒ３、Ｒ’ 、Ｒ’ 、Ｒ”はハロゲン
原子、炭素数１〜４のアルキル基又はアルシコキシ基で
互いに同−又は異なってもよく、Ｐ’−Ｑｚｒ及びＳは
０．１又は２、ｎは０又は１である。）
ジアミン、
テトラカルボン酸２無水物、
及び−綴代（ＩＩ）で表される
Ｒ？→Ｒ” ＋ｙ Ｎ ＩＩ□ （
Ｉｆ）（式中、Ｒ？は２価の有機基、Ｒ８は炭素数６〜
２０のアルキル基、ｍは０又はｌである。）モノアミン
から得られるポリイミド樹脂よりなる液晶セル用配向処
理剤であり、詳しくは一般式％式％
（式中、Ｒ′及びＲ２は互いに同−又は異る炭素数１〜
６のパーフルオロアルキル基、Ｒ３、Ｒ’ 、Ｒ５、Ｒ
ｈはハロゲン原子、炭素数１〜４のアルキル基又はアル
シコキシ基で互いに同−又は異なってもよく、Ｐ％ ｑ
％ ’及びＳは０、ｌ又は２、ｎは０又は１である。）
ラフ４フ８
テトラカルボン酸２無水物ｂモル
及び−綴代（Ｕ）で表される
Ｒ７→Ｒ ’ 十ＴＮｌｌｚ （
ＩＩ ）（式中、Ｒ７は２価の有機基、Ｒ１′は炭素
数６〜２０のアルキル基、ｍは０又はｌである。）モノ
アミンＣモルを、次式で表される
ｂａａ≧ｂ ／ ２ （１）２
（ｂ−ａ）≧ｃ ＞ Ｏ（２）
関係で反応、重合させて得られるポリイミド樹脂よりな
る液晶セル用配向処理剤に関するものである。That is, the present invention is represented by the general formula (1) (wherein R1 and Rg are the same or different perfluoroalkyl i having 1 to 6 carbon atoms, R3, R', R', R'' are A halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group, which may be the same or different from each other, P'-Qzr and S are 0.1 or 2, and n is 0 or 1.) diamine, tetracarboxylic Acid dianhydride, and R?→R” +y N II□ (
If) (in the formula, R? is a divalent organic group, R8 is a carbon number of 6 to
20 alkyl groups, m is 0 or l. ) It is an alignment treatment agent for liquid crystal cells made of polyimide resin obtained from monoamine, and in detail, it has the general formula % (in the formula, R' and R2 have the same or different carbon numbers 1 to 1).
6 perfluoroalkyl group, R3, R', R5, R
h is a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group, which may be the same or different from each other, and P% q
%' and S are 0, l or 2, and n is 0 or 1. ) Rough 4 F8 Tetracarboxylic dianhydride b mol and - R7 → R ' 10TNllz (
II) (In the formula, R7 is a divalent organic group, R1' is an alkyl group having 6 to 20 carbon atoms, and m is 0 or l). 2 (1)2
The present invention relates to an alignment treatment agent for liquid crystal cells made of a polyimide resin obtained by reaction and polymerization in the relationship (ba)≧c>O(2).
本発明の液晶セル用配向処理剤は、透明電極の付いたガ
ラス或いはプラスチックフィルム等の透明基板上にポリ
イミド樹脂膜を形成せしめ、次いでラビング処理を施す
ことによって、液晶セル用配向処理剤として使用するも
のである。The alignment treatment agent for liquid crystal cells of the present invention is used as an alignment treatment agent for liquid crystal cells by forming a polyimide resin film on a transparent substrate such as glass or plastic film with a transparent electrode, and then subjecting it to a rubbing treatment. It is something.
本発明の液晶セル用配向処理剤に使用される一般式（１
）のジアミン化合物の具体例としては、１．１，１，３
，３．３−ヘキサフルオロ−２，２−ビス〔４−（４−
アミノフェノキシ）フェニル〕プロパン、１．１，１．
３．３．３−へキサフルオロ−２，２−ビス〔３゜５−
ジメチル−４−（４−アミノフェノキシ）フェニル〕プ
ロパン、１，１．１，３．３．３−ヘキサフルオロ−２
，２−ビス〔３，５−ジブロモ−４（４−アミノフェノ
キシ）フェニル〕プロパン、１，１．１，３，３゜３−
へキサフルオロ−２，２−ビス〔３−メチル−４−（４
−アミノフェノキシ）フェニル〕プロパン、１，１．１
．３．３．３−ヘキサフルオロ−２，２−ビス（４−（
３−アミノフェノキシ）フェニル〕プロパン、１．１，
１，３，３．４，４．４−オクタフルオロ−２，２−ビ
ス（４−（４−アミノフェノキシ）フェニルコブタン、
１，１．１，２．２，４．４，５．５．５−デカフルオ
ロ−３，３−ヒス（４−（４−アミノフェノキシ）フェ
ニル〕ペンタン、１．１，１．３．３．３−へキサフル
オロ＝２．２−ヒス（４−アミノフェニル）プロパン、
１゜１．１，３，３．３−へキサフルオロ−２，２−ビ
ス（３−アミノフェニル）プロパン、１．１．１．３，
３．３−へキサフルオロ−２，２−ビス（３−メチル−
４−アミノフェニル）プロパン、１．１．１，３，３，
４，４．１−オクタフルオロ−２，２−ビス（４−アミ
ノフェニル）ブタン等が挙げられる。General formula (1) used in the alignment treatment agent for liquid crystal cells of the present invention
) Specific examples of diamine compounds include 1.1, 1, 3
,3.3-hexafluoro-2,2-bis[4-(4-
Aminophenoxy)phenyl]propane, 1.1,1.
3.3.3-Hexafluoro-2,2-bis[3゜5-
Dimethyl-4-(4-aminophenoxy)phenyl]propane, 1,1.1,3.3.3-hexafluoro-2
,2-bis[3,5-dibromo-4(4-aminophenoxy)phenyl]propane, 1,1.1,3,3゜3-
Hexafluoro-2,2-bis[3-methyl-4-(4
-aminophenoxy)phenyl]propane, 1,1.1
．． 3.3.3-hexafluoro-2,2-bis(4-(
3-aminophenoxy)phenyl]propane, 1.1,
1,3,3.4,4.4-octafluoro-2,2-bis(4-(4-aminophenoxy)phenylcobutane,
1,1.1,2.2,4.4,5.5.5-decafluoro-3,3-his(4-(4-aminophenoxy)phenyl)pentane, 1.1,1.3.3 .3-hexafluoro=2.2-his(4-aminophenyl)propane,
1゜1.1,3,3.3-hexafluoro-2,2-bis(3-aminophenyl)propane, 1.1.1.3,
3.3-hexafluoro-2,2-bis(3-methyl-
4-aminophenyl)propane, 1.1.1,3,3,
Examples include 4,4.1-octafluoro-2,2-bis(4-aminophenyl)butane.
又、これらジアミンの１種又は２種以上を混合して使用
することもできる。Further, these diamines may be used alone or in combination of two or more.
本発明の液晶セル用配向処理剤に使用されるテトラカル
ボン酸２無水物の具体例としては、ピロメリット酸２無
水物、ベンゾフェノンテトラカルボン酸２無水物及びビ
フェニルテトラカルボン酸２無水物等の芳香族テトラカ
ルボン酸２無水物、シクロブタンテトラカルボン酸２無
水物、シクロペンクンテトラカルボン酸２無水物及びシ
クロヘキサンテトラカルボン酸２無水物等の脂環式テト
ラカルボン酸２無水物、ブタンテトラカルボン酸２無水
物等の脂肪族テトラカルボン酸２無水物等が挙げられる
。Specific examples of the tetracarboxylic dianhydride used in the alignment treatment agent for liquid crystal cells of the present invention include pyromellitic dianhydride, benzophenone tetracarboxylic dianhydride, and biphenyltetracarboxylic dianhydride. Alicyclic tetracarboxylic dianhydrides such as group tetracarboxylic dianhydride, cyclobutanetetracarboxylic dianhydride, cyclopenkunetetracarboxylic dianhydride, and cyclohexanetetracarboxylic dianhydride, butanetetracarboxylic dianhydride Examples include aliphatic tetracarboxylic acid dianhydrides such as anhydrides.
又、これらテトラカルボン酸２無水物は１種であっても
２種以上混合して使用しても良い。Further, these tetracarboxylic dianhydrides may be used alone or in combination of two or more.
−Ｃ式（Ｈ）のモノアミンの２価の有ａ基Ｒ’は、脂肪
族基及びその誘導体又は芳香族基及びその誘導体である
。The divalent a group R' of the monoamine of the -C formula (H) is an aliphatic group and its derivatives, or an aromatic group and its derivatives.
一般式（ｎ）のモノアミンの具体例としては、ｎ−ヘキ
シルアミン、ｎ−オクチルアミン、ｎ −デシルアミン
、ｎ−ドデシルアミン、ｎ−ヘキサデシルアミン、１．
３−ジメチルブチルアミン、１゜５−ジメチルヘキシル
アミン及び２−エチルヘキシルアミン等の脂肪族アミン
、Ｐ−アミノフェニルヘキサン、ｐ−アミノフェニルオ
クタン、ｐ−アミノフェニルドデカン、ｐ−アミノフェ
ニルヘキサンカンン、ｐ−アミノフェノキシオクタン、
ｐ−アミノフェノキシドデカン、ｐ−アミノフェノキシ
ヘキサデカン等の芳香族アミンが挙げられる。Specific examples of the monoamine of general formula (n) include n-hexylamine, n-octylamine, n-decylamine, n-dodecylamine, n-hexadecylamine, 1.
Aliphatic amines such as 3-dimethylbutylamine, 1゜5-dimethylhexylamine and 2-ethylhexylamine, p-aminophenylhexane, p-aminophenyl octane, p-aminophenyldodecane, p-aminophenylhexane, p -aminophenoxyoctane,
Aromatic amines such as p-aminophenoxydodecane and p-aminophenoxyhexadecane are mentioned.
又、これらモノアミンは、単独に或いは２′Ｍ１以上混
合して使用することができる。Further, these monoamines can be used alone or in a mixture of 2'M1 or more.
−綴代（Ｉｆ）のモノアミンのアルキル基であるＲ″の
炭素数が５以下の時は、液晶分子の傾斜配向角を高める
効果が充分でない。- When the carbon number of R'', which is the alkyl group of the monoamine of the binding margin (If), is 5 or less, the effect of increasing the tilt orientation angle of the liquid crystal molecules is not sufficient.
又、Ｒ２の炭素数が２０を超えると基板への塗布性が悪
化する等の不都合が生じ易くなる。Furthermore, if the number of carbon atoms in R2 exceeds 20, problems such as poor applicability to a substrate tend to occur.
本発明の液晶セル用配向処理剤は、−綴代（１）のジア
ミン８モル、テトラカルボン酸２無水物ｂモル及び−綴
代（ｎ）のモノアミンＣモルを、次式で表される
ｂａａ≧ｂ ／ ２ （１）２
（ｂ−ａ’）≧ｃ ＞ ｏ （２）関
係で反応、重合させて得られるポリイミド樹脂を使用す
る必要がある。The alignment treatment agent for liquid crystal cells of the present invention contains 8 moles of diamine in the binding margin (1), b moles of tetracarboxylic dianhydride, and C moles of the monoamine in the binding margin (n), which is expressed by the following formula: baa ≧b/2 (1)2
(ba')≧c>o (2) According to the relationship, it is necessary to use a polyimide resin obtained by reaction and polymerization.
ここで、ｂ≦ａでは一般式（ＩＩ）のモノアミンの反応
及び重合が充分でないため液晶セル用配向処理剤として
使用した場合、液晶分子を大きく傾斜配向することがで
きない。Here, when b≦a, the reaction and polymerization of the monoamine of general formula (II) is insufficient, and therefore, when used as an alignment treatment agent for liquid crystal cells, liquid crystal molecules cannot be aligned with a large tilt.
又、ａ ＜ ｂ ／ ２では、ポリイミド樹脂の重合度
が上昇しないため、液晶セル用配向処理剤として安定な
塗膜を形成することができない。Further, when a<b/2, the degree of polymerization of the polyimide resin does not increase, and therefore a stable coating film cannot be formed as an alignment treatment agent for liquid crystal cells.
更に、２（ｂ−ａ）＜ｃでは、液晶セル用配向処理剤と
して使用した場合、液晶セル内で一般式（ＩＩ）のモノ
アミンが遊離し液晶セルの表示特性に悪影響を与える場
合がある。Furthermore, when 2(ba)<c, when used as an alignment treatment agent for a liquid crystal cell, the monoamine of general formula (II) may be liberated within the liquid crystal cell, which may adversely affect the display characteristics of the liquid crystal cell.
一般式（１）のジアミン、テトラカルボン酸２無水物及
び−綴代（ｎ）のモノアミンの反応及び重合方法は特に
限定する必要はない。There is no need to particularly limit the reaction and polymerization method of the diamine of general formula (1), the tetracarboxylic dianhydride, and the monoamine of -tsusuriyo (n).
一般に、−綴代（１）のジアミンとテトラカルボン酸２
無水物を反応後、−ａ式（ＩＩ）のモノアミンを反応、
重合させたり、これら三成分を同時に反応、重合させる
方法を採用することができる。Generally, the diamine and tetracarboxylic acid 2 of - binding margin (1)
After reacting the anhydride, -a reacting the monoamine of formula (II),
It is possible to adopt a method of polymerizing or simultaneously reacting and polymerizing these three components.
更に、−綴代ＣＩ）のジアミン、テトラカルボン酸２無
水物及び−綴代〔■〕のモノアミンを反応させた後、ポ
リイミド樹脂膜とする方法は、加工面の容易さから一般
式（１）のジアミン、テトラカルボン酸２無水物及び−
綴代（ＩＩ）のモノアミンを反応しポリアミック酸中間
体とした後、該中間体を脱水閉環する方法が望ましい。Furthermore, a method for forming a polyimide resin film by reacting the diamine of -Tsuriyoshi CI), tetracarboxylic dianhydride, and the monoamine of -Tsuriyoshi [■] is based on the general formula (1) from the viewpoint of ease of processing. diamine, tetracarboxylic dianhydride and -
A preferred method is to react the monoamine of the margin (II) to form a polyamic acid intermediate, and then dehydrate and ring-close the intermediate.
この場合、生成するポリアミック酸中間体を単離せずに
ポリイミド樹脂とする１段法或いは生成するポリアミッ
ク酸中間体を単離し、次いで脱水閉環重合してポリイミ
ド樹脂とする２段法のいずれの方法も採用出来る。In this case, either a one-step method in which the polyamic acid intermediate produced is made into a polyimide resin without isolating it, or a two-step method in which the produced polyamic acid intermediate is isolated and then subjected to dehydration ring-closing polymerization to produce a polyimide resin. Can be hired.
一般式（１）のジアミン、テトラカルボン酸２無水物及
び−綴代（１１）のモノアミンの反応、重合温度は一２
０〜４００°Ｃの任意の温度を採用することができるが
、特に、−５〜３５０ ’Ｃの範囲が好ましい。The reaction of the diamine of the general formula (1), the tetracarboxylic dianhydride, and the monoamine of the -Tsuzuriyo (11), the polymerization temperature is -2
Although any temperature between 0 and 400°C can be employed, a range of -5 to 350'C is particularly preferred.
又、ポリアミック酸中間体生成のための反応温度は一２
０〜１５０°Ｃの任意の温度を選択することができるが
、特に−５〜１００°Ｃの範囲が好ま″しい。In addition, the reaction temperature for producing polyamic acid intermediate is -2
Any temperature in the range of 0 to 150°C can be selected, but a range of -5 to 100°C is particularly preferred.
更に、ポリアミック酸中間体をポリイミド樹脂に転化す
るには、通常は加熱により脱水閉環する方法が採用され
る。この加熱脱水閉環温度は、１５０〜４５０℃、好ま
しくは１７０〜３５０℃の任意の温度を選択することが
できる。Furthermore, in order to convert the polyamic acid intermediate into a polyimide resin, a method of dehydration and ring closure by heating is usually employed. This thermal dehydration ring-closing temperature can be selected from any temperature from 150 to 450°C, preferably from 170 to 350°C.
又、この脱水閉環に要する時間は、上記反応温度にもよ
るが３０秒〜１０時間、好ましくは５分〜５時間が適当
である。The time required for this dehydration ring closure is suitably 30 seconds to 10 hours, preferably 5 minutes to 5 hours, although it depends on the reaction temperature.
ポリアミック酸中間体をポリイミド樹脂に転化する他の
方法として、公知の脱水閉環触媒を使用して化学的に閉
環することもできる。Another method for converting the polyamic acid intermediate into a polyimide resin is chemical ring closure using a known dehydration ring closure catalyst.
本発明の一般式（１）のジアミン、テトラカルボン酸２
ｇ水物及び−綴代（ＩＩ）のモノアミンから得られるポ
リイミド樹脂又はポリアミック酸中間体溶液を、透明電
極の付いたガラス又はプラスチックフィルム等の透明基
板上にスピンコード法もしくは印刷法等により塗布した
後、１５０〜２５０°Ｃで１分間〜２時間で硬化せしめ
■りＪ！；ｒ、２００〜３０００人のポリイミド樹脂膜
を形成し、次いでポリイミド樹脂膜層をラビング処理し
液晶セル用配向処理剤とすることができる。Diamine of general formula (1) of the present invention, tetracarboxylic acid 2
A polyimide resin or polyamic acid intermediate solution obtained from the monoamine of g-water and Tsuzushiyo (II) was applied onto a transparent substrate such as a glass or plastic film with a transparent electrode by a spin code method or a printing method. After that, cure at 150-250°C for 1 minute to 2 hours. ;r, a polyimide resin film of 200 to 3000 layers is formed, and then the polyimide resin film layer is subjected to a rubbing treatment to obtain an alignment treatment agent for a liquid crystal cell.
（ホ）発明の効果
本発明の液晶セル配向処理剤は、液晶傾斜配向角が大き
い液晶セル用配向処理剤として使用することができる。(e) Effects of the Invention The liquid crystal cell alignment agent of the present invention can be used as an alignment agent for liquid crystal cells having a large liquid crystal tilt alignment angle.
又、−綴代〔１〕のジアミンをａモル、テトラカルボン
酸２無水物をｂモルとすると、−綴代（ＩＩ）のモノア
ミンＣモルは、次式で表されるｂａａ≧ｂ ／ ２
（１）２（ｂ−ａ）≧ｃ ＞ ０
（２）関係を満足する限り、液晶傾斜配向角
を任意に調節することが可能である。Moreover, if the diamine of -Tsuriyo [1] is a mole and the tetracarboxylic dianhydride is b mole, then the monoamine C mole of -Tsuriyo (II) is expressed by the following formula: baa≧b/2
(1) 2(b-a)≧c>0
(2) As long as the relationship is satisfied, it is possible to arbitrarily adjust the liquid crystal tilt orientation angle.
（へ）実施例
以下に実施例を挙げ、本発明を更に詳しく説明するが本
発明はこれらに限定されるものではない。(f) Examples The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited thereto.
実施例１
１．１．１．３．３．３−へキサフルオロ−２，２−ビ
ス〔４−（４−アミノフェノキシ）フェニル〕プロパン
３７．３３ ｇ （０，０７２モル）、ｎ−ヘキサデシ
ルデミン３．８５ ｇ （０，０１６モル）及びシクロ
ブタンテトラカルボン酸２無水物１５．６９ ｇ （０
，０８モル）をＮＭＰ５１２ｇ中、室温で４時間攪拌反
応させポリアミック酸中間体溶液を調製した。Example 1 1.1.1.3.3.3-hexafluoro-2,2-bis[4-(4-aminophenoxy)phenyl]propane 37.33 g (0,072 mol), n-hexadecyl Demine 3.85 g (0,016 mol) and cyclobutanetetracarboxylic dianhydride 15.69 g (0
, 08 mol) in 512 g of NMP at room temperature for 4 hours to prepare a polyamic acid intermediate solution.
得られたポリアミック酸中間体の還元粘度η３，７ｃは
０．５１ ｄ １／ｇ （０，５重景％ＮＭＰ溶液、３
０°Ｃ）であった。The reduced viscosity η3,7c of the obtained polyamic acid intermediate is 0.51 d 1/g (0.5% NMP solution, 3
0°C).
この溶液を、ＮＭＰにより総固型分を２重量％に希釈後
、透明電極付ガラス基板に３５０Ｏｒｐｍでスピンコー
ドし、１７０℃で６０分間熱処理して均一なポリイミド
樹脂膜が得られた。This solution was diluted with NMP to a total solid content of 2% by weight, spin-coded onto a glass substrate with a transparent electrode at 350 rpm, and heat-treated at 170° C. for 60 minutes to obtain a uniform polyimide resin film.
この塗膜を布でラビングした後、５０μのスペーサーを
挟んでラビング方向を平行にして組立て、液晶（メルク
社製：Ｚｌ、Ｉ−２２９３）を注入してホモジニアス配
向したセルを作成した。After rubbing this coating film with a cloth, it was assembled with a 50 μm spacer in between so that the rubbing directions were parallel to each other, and a liquid crystal (manufactured by Merck & Co., Ltd.: Zl, I-2293) was injected to create a homogeneously oriented cell.
このセルをクロスニコル中で回転したところ明瞭な明Ｍ
が認められ、ラビング方向へ良好に配向していることが
確認された。When this cell was rotated in a crossed nicol, a clear M
was observed, and it was confirmed that the particles were well oriented in the rubbing direction.
又、このセルについて磁場容量法で液晶傾斜配向角を測
定したところ３０°であった。Further, when the liquid crystal tilt orientation angle of this cell was measured using a magnetic field capacitance method, it was found to be 30°.
比較例１
２．２−ビス（４−（４−アミノフェノキシ）フェニル
〕プロパン２９．５２ ｇ （０，０７２モル）、ｎ−
ヘキサデシルアミ：／３．８５ ｇ （０，０１６−’
Ｅル）及びシクロブタンテトラカルボン酸２無水物１５
゜６９ｇ（０，０８モル）をＮ−メチル−２−ピロリド
ン（以下、ＮＭＰと略称する。）４２２ｇ中、室温で４
時間反応させポリアミック酸中間体溶液を調製した。Comparative Example 1 2.2-bis(4-(4-aminophenoxy)phenyl)propane 29.52 g (0,072 mol), n-
Hexadecylamine: /3.85 g (0,016-'
E) and cyclobutanetetracarboxylic dianhydride 15
゜69g (0.08 mol) was dissolved in 422g of N-methyl-2-pyrrolidone (hereinafter abbreviated as NMP) at room temperature.
A polyamic acid intermediate solution was prepared by reacting for a period of time.
得られたポリアミック酸中間体の還元粘度７７５ｐｙｃ
は０．５２ ｄ ｌ／ｇ （０，５重量％ＮＭＰ溶液、
３０°Ｃ）であった。Reduced viscosity of the obtained polyamic acid intermediate: 775 pyc
is 0.52 dl/g (0.5% by weight NMP solution,
30°C).
この溶液をＮＭＰにより総固形分を２ｉ１％に希釈後、
実施例１と同様にしてセルを作製した。After diluting this solution with NMP to a total solid content of 2i1%,
A cell was produced in the same manner as in Example 1.
液晶傾斜配向角は１９°であり配向も良好であった。The liquid crystal tilt orientation angle was 19°, and the orientation was also good.
Claims (1)
１〜６のパーフルオロアルキル基、Ｒ＾３、Ｒ＾４、Ｒ
＾５、Ｒ＾６はハロゲン原子、炭素数１〜４のアルキル
基又はアルシコキシ基で互いに同一又は異なってもよく
、ｐ、ｑ、ｒ及びｓは０、１又は２、ｎは０又は１であ
る。）ジアミン、 テトラカルボン酸２無水物、 及び一般式〔II〕で表される ▲数式、化学式、表等があります▼〔II〕 （式中、Ｒ＾７は２価の有機基、Ｒ＾８は炭素数６〜２
０のアルキル基、ｍは０又は１である。）モノアミンか
ら得られるポリイミド樹脂よりなる配向処理剤。 ２、一般式〔 I 〕で表される ▲数式、化学式、表等があります▼〔 I 〕 （式中、Ｒ＾１及びＲ＾２は互いに同一又は異る炭素数
１〜６のパーフルオロアルキル基、Ｒ＾３、Ｒ＾４、Ｒ
＾５、Ｒ＾６はハロゲン原子、炭素数１〜４のアルキル
基又はアルシコキシ基で互いに同一又は異なってもよく
、ｐ、ｑ、ｒ及びｓは０、１又は２、ｎは０又は１であ
る。）ジアミンａモル、 テトラカルボン酸２無水物ｂモル、 及び一般式〔II〕で表される ▲数式、化学式、表等があります▼〔II〕 （式中、Ｒ＾７は２価の有機基、Ｒ＾８は炭素数６〜２
０のアルキル基、ｍは０又は１である。）モノアミンｃ
モルを、次式で表される ｂ＞ａ≧ｂ／２（１） ２（ｂ−ａ）≧ｃ＞０（２） 関係で反応、重合させて得られるポリイミド樹脂よりな
る請求項１記載の配向処理剤。[Claims] 1. There are ▲ mathematical formulas, chemical formulas, tables, etc. represented by the general formula [I] ▼ [I] (wherein R^1 and R^2 are carbon numbers 1 that are the same or different from each other) ~6 perfluoroalkyl groups, R^3, R^4, R
^5 and R^6 are halogen atoms, alkyl groups having 1 to 4 carbon atoms, or alkoxy groups, which may be the same or different from each other, p, q, r and s are 0, 1 or 2, and n is 0 or 1. be. ) diamine, tetracarboxylic dianhydride, and general formula [II] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] (In the formula, R^7 is a divalent organic group, R^8 has 6 to 2 carbon atoms
0 alkyl group, m is 0 or 1. ) An alignment treatment agent made of polyimide resin obtained from monoamine. 2. There are ▲mathematical formulas, chemical formulas, tables, etc. represented by the general formula [I]▼[I] (wherein R^1 and R^2 are perfluoroalkyl having 1 to 6 carbon atoms, which are the same or different from each other) Group, R^3, R^4, R
^5 and R^6 are halogen atoms, alkyl groups having 1 to 4 carbon atoms, or alkoxy groups, which may be the same or different from each other, p, q, r and s are 0, 1 or 2, and n is 0 or 1. be. ) A mol of diamine, b mol of tetracarboxylic dianhydride, and ▲ Numerical formulas, chemical formulas, tables, etc. represented by the general formula [II] ▼ [II] (In the formula, R^7 is a divalent organic group , R^8 has 6 to 2 carbon atoms
0 alkyl group, m is 0 or 1. ) monoamine c
2. The polyimide resin according to claim 1, which is made of a polyimide resin obtained by reacting and polymerizing the moles of b>a≧b/2(1) 2(ba-a)≧c>0(2) expressed by the following formula. Orientation treatment agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP436588A JPH01180518A (en) | 1988-01-12 | 1988-01-12 | Orientation treating agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP436588A JPH01180518A (en) | 1988-01-12 | 1988-01-12 | Orientation treating agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01180518A true JPH01180518A (en) | 1989-07-18 |
Family
ID=11582349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP436588A Pending JPH01180518A (en) | 1988-01-12 | 1988-01-12 | Orientation treating agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01180518A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01262528A (en) * | 1988-04-14 | 1989-10-19 | Nissan Chem Ind Ltd | Composition for liquid crystal orienting agent |
| JPH03171033A (en) * | 1989-11-30 | 1991-07-24 | Mitsui Toatsu Chem Inc | Orienting agent for liquid crystal panel |
| JPH04161923A (en) * | 1990-10-25 | 1992-06-05 | Canon Inc | Liquid crystal display element |
| EP0507293A2 (en) * | 1991-04-04 | 1992-10-07 | E.I. Du Pont De Nemours And Company | Liquid crystal displays of high tilt bias angles |
| US5420233A (en) * | 1992-06-23 | 1995-05-30 | Nissan Chemical Industries Ltd. | Agent for vertical orientation treatment |
| US5520845A (en) * | 1993-12-02 | 1996-05-28 | E. I. Du Pont De Nemours And Company | Poly(2,6-piperazinedione) alignment layer for liquid crystal displays |
| US5571579A (en) * | 1992-07-24 | 1996-11-05 | Hitachi Chemical Company, Ltd | Alignment film for liquid crystal, liquid crystal-sandwiched panel, liquid crystal display module and material for liquid crystal alignment film |
| JP2002506466A (en) * | 1997-05-20 | 2002-02-26 | エルシコン・インコーポレーテッド | Amine fluoride substance |
| KR100745307B1 (en) * | 2001-05-31 | 2007-08-01 | 사노피-아벤티스 | Aminoquinoline derivatives and their use as adenosine a3 ligands |
| JP4639471B2 (en) * | 1998-10-13 | 2011-02-23 | 日産化学工業株式会社 | Polyimide material |
| CN104073261A (en) * | 2013-03-26 | 2014-10-01 | 达兴材料股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element |
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|---|---|---|---|---|
| JPS62174725A (en) * | 1985-09-27 | 1987-07-31 | Sanyo Electric Co Ltd | Liquid crystal display device |
| JPS62297819A (en) * | 1986-06-18 | 1987-12-25 | Nissan Chem Ind Ltd | Orientating agent for liquid crystal cell |
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- 1988-01-12 JP JP436588A patent/JPH01180518A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62174725A (en) * | 1985-09-27 | 1987-07-31 | Sanyo Electric Co Ltd | Liquid crystal display device |
| JPS62297819A (en) * | 1986-06-18 | 1987-12-25 | Nissan Chem Ind Ltd | Orientating agent for liquid crystal cell |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01262528A (en) * | 1988-04-14 | 1989-10-19 | Nissan Chem Ind Ltd | Composition for liquid crystal orienting agent |
| JPH03171033A (en) * | 1989-11-30 | 1991-07-24 | Mitsui Toatsu Chem Inc | Orienting agent for liquid crystal panel |
| JPH04161923A (en) * | 1990-10-25 | 1992-06-05 | Canon Inc | Liquid crystal display element |
| EP0507293A2 (en) * | 1991-04-04 | 1992-10-07 | E.I. Du Pont De Nemours And Company | Liquid crystal displays of high tilt bias angles |
| US5420233A (en) * | 1992-06-23 | 1995-05-30 | Nissan Chemical Industries Ltd. | Agent for vertical orientation treatment |
| US5571579A (en) * | 1992-07-24 | 1996-11-05 | Hitachi Chemical Company, Ltd | Alignment film for liquid crystal, liquid crystal-sandwiched panel, liquid crystal display module and material for liquid crystal alignment film |
| US5520845A (en) * | 1993-12-02 | 1996-05-28 | E. I. Du Pont De Nemours And Company | Poly(2,6-piperazinedione) alignment layer for liquid crystal displays |
| JP2002506466A (en) * | 1997-05-20 | 2002-02-26 | エルシコン・インコーポレーテッド | Amine fluoride substance |
| JP4639471B2 (en) * | 1998-10-13 | 2011-02-23 | 日産化学工業株式会社 | Polyimide material |
| KR100745307B1 (en) * | 2001-05-31 | 2007-08-01 | 사노피-아벤티스 | Aminoquinoline derivatives and their use as adenosine a3 ligands |
| CN104073261A (en) * | 2013-03-26 | 2014-10-01 | 达兴材料股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element |
| JP2014191352A (en) * | 2013-03-26 | 2014-10-06 | Daxin Material Corp | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element thereof |
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