JPH02223916A - Formation of oriented film - Google Patents
Formation of oriented filmInfo
- Publication number
- JPH02223916A JPH02223916A JP4559689A JP4559689A JPH02223916A JP H02223916 A JPH02223916 A JP H02223916A JP 4559689 A JP4559689 A JP 4559689A JP 4559689 A JP4559689 A JP 4559689A JP H02223916 A JPH02223916 A JP H02223916A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- substrate
- angle
- diamine
- tetracarboxylic anhydride
- 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.)
- Granted
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 31
- 239000000758 substrate Substances 0.000 claims abstract description 25
- -1 tetracarboxylic anhydride Chemical class 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 5
- 210000002858 crystal cell Anatomy 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 abstract description 15
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 229920001721 polyimide Polymers 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 4
- 239000004642 Polyimide Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 3
- 239000009719 polyimide resin Substances 0.000 abstract description 3
- 238000001354 calcination Methods 0.000 abstract 2
- 238000005516 engineering process Methods 0.000 description 5
- 238000010304 firing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-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
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は液晶表示体用液晶セルの配向膜の作成方法に関
する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for producing an alignment film for a liquid crystal cell for a liquid crystal display.
近年、液晶表示体技術の発展は著しく、液晶テレビ等へ
の応用が可能となった。この液晶表示体は第１図に示す
如く二枚の透明電極（１２）付き基板（１１）と液晶（
１−４）と配向膜（１３）よりなっている。In recent years, the development of liquid crystal display technology has been remarkable, and it has become possible to apply it to liquid crystal televisions and the like. As shown in Fig. 1, this liquid crystal display consists of a substrate (11) with two transparent electrodes (12) and a liquid crystal (
1-4) and an alignment film (13).
液晶テレビに使われるアクティーブマトリクス駆動の場
合、画素が独立に駆動されるため、配向技術に関しては
従来の技術で問題にはならなかった。しかし、この場合
、歩留まりが悪く高価になる欠点がある。In the case of active matrix drive used in LCD televisions, the pixels are driven independently, so there was no problem with conventional alignment technology. However, in this case, there is a drawback that the yield is low and the cost is high.
一方、単純マトリクス駆動方式によれば、安価になる可
能性があるためアクテイーブ方式の代替が考えられてい
る。On the other hand, the simple matrix drive method is considered to be an alternative to the active method because it may be cheaper.
これら代替技術は、ＳＢＥ方式、ＮＴＮ方式等とよばれ
ている。These alternative technologies are called SBE method, NTN method, etc.
この技術の重要な点は、従来の液晶表示体の液晶分子が
９０度ツイストしているのに対して、１−８０度以上ツ
イストしていることである。The important point of this technology is that the liquid crystal molecules of conventional liquid crystal display bodies are twisted by 90 degrees, but are twisted by 1 to 80 degrees or more.
このため液晶分子を基板に対して５度以上たたせ、過度
のネジレによる歪を逃がしてやる必要がある。５度以上
立たせる方法の一つとして配向膜による方法がある。For this reason, it is necessary to tilt the liquid crystal molecules against the substrate at an angle of 5 degrees or more to release distortion caused by excessive twisting. One of the methods to make the angle 5 degrees or more is to use an alignment film.
１８０度以上液晶分子をツイストさせる従来の配向膜の
作成方法は、単一成分のポリイミド系樹脂を塗布する方
法であった。The conventional method for creating an alignment film that twists liquid crystal molecules by 180 degrees or more is to apply a single-component polyimide resin.
液晶表示体のコントラストを最善の状態にするためには
液晶の種類、液晶のネジレ角度に対応して基板との角度
を最適化しなければならない。In order to achieve the best contrast of a liquid crystal display, the angle with the substrate must be optimized depending on the type of liquid crystal and the twist angle of the liquid crystal.
しかし、単一成分を用いるため任意に基板との角度を変
えることはできなかった。However, since a single component was used, it was not possible to arbitrarily change the angle with the substrate.
叉多成分によって変えようとしても、単一成分で基板と
の角度を大きく変えるような成分が無かったため不可能
であった。Even if an attempt was made to change the angle using multiple components, it was impossible because there was no single component that could significantly change the angle with the substrate.
本発明の従来の配向膜のこのような欠点を改良するため
になされたもので、っぎの構造式を有すジアミン化合物
（１）と他のジアミン化合物（２）とテトラカルボン酸
無水物を溶解した溶液を塗布した後、乾燥、焼成してか
らラビングすることを特徴とする。The present invention was made in order to improve such drawbacks of the conventional alignment film, and it is made by dissolving a diamine compound (1) having the structural formula of After applying the solution, it is dried, baked, and then rubbed.
（但し、Ｒは水素叉はアルキル基を示す。）ジアミン系
化合物（２）としてはつぎのような化合物が考えられる
。(However, R represents hydrogen or an alkyl group.) As the diamine compound (2), the following compounds can be considered.
１、 ４．４’ −ジアミノジフェニルエーテル２、
４．４’ −ジアミノジフェニルメタン３、 ｐ−
フェニレンジアミン
４、 ｍ−フェニレンジアミン
５、 ｍ−キシレンジアミン
６．４．４′−ジアミノチルベン
７、 １．４−ジアミノシクロヘキサン８．１．６−
ジアミツヘキサン
９、 Ｂｉｓ−Ｍ（三井石油化学社製）１０、Ｂ１５
−Ｐ（三井石油化学社製）このような化合物は一例であ
り、ジアミン系化合物（２）としては、上記化合物のほ
かにも色々考えることが出来るものである。1, 4.4'-diaminodiphenyl ether 2,
4.4'-diaminodiphenylmethane 3, p-
phenylenediamine 4, m-phenylenediamine 5, m-xylenediamine 6.4.4'-diaminothilbene 7, 1.4-diaminocyclohexane 8.1.6-
Diamithexane 9, Bis-M (manufactured by Mitsui Petrochemicals) 10, B15
-P (manufactured by Mitsui Petrochemical Co., Ltd.) Such a compound is just an example, and various other compounds can be considered as the diamine compound (2) in addition to the above compounds.
又、テトラカルボン酸無水物としては、無水ピロメリッ
ト酸、ベンゾフェノンテトラカルボン酸無水物、ヘキサ
フルオロプロピリデンシフタル酸無水物、ビフェニルテ
トラカルボン酸無水物等色々考えられる。Various types of tetracarboxylic anhydride can be considered, such as pyromellitic anhydride, benzophenonetetracarboxylic anhydride, hexafluoropropylidene cyphthalic anhydride, and biphenyltetracarboxylic anhydride.
乾燥、焼成条件、ラビング条件等は従来のポリイミド系
配向膜を作成する条件がそのまま適用出来る。As for drying, firing conditions, rubbing conditions, etc., conventional conditions for producing a polyimide alignment film can be applied as they are.
塗布方法としては、スピンコード法、デイピング法、キ
ャスティング法、ハケ塗り法等いずれも可能であるがス
ピンコード法が優れている。As a coating method, any of the spin-coding method, dipping method, casting method, brushing method, etc. is possible, but the spin-coding method is superior.
本発明の配向膜の作成方法によれば、配向膜はポリイミ
ド樹脂よりなるため、ポリイミドの特徴・である耐熱性
に優れるという特性を有する。According to the method for producing an alignment film of the present invention, since the alignment film is made of polyimide resin, it has excellent heat resistance, which is a characteristic of polyimide.
基板に対する液晶分子の角度は、２成分のジアミン化合
物の混合割合を変えることにより数度（０〜５度）から
２２度まで自由に変えることが出来る。The angle of the liquid crystal molecules with respect to the substrate can be freely changed from several degrees (0 to 5 degrees) to 22 degrees by changing the mixing ratio of the two diamine compounds.
２種のジアミン化合物を混合した配向膜により達成され
る液晶分子と基板との角度と、各ジアミンとテトラカル
ボンサン無水物よりなる配向膜により達成される角度と
の間にはほぼ加成性が成り立つ。There is almost no additivity between the angle between the liquid crystal molecules and the substrate achieved by an alignment film made of a mixture of two types of diamine compounds and the angle achieved by an alignment film made of each diamine and tetracarboxylic anhydride. It works.
以下、実施例により本発明の詳細な説明する。Hereinafter, the present invention will be explained in detail with reference to Examples.
〔実施例１〕
次の構造式を有す２ｔｌｉのジアミンとテトラカルボン
酸無水物を表１の割合で混合した１０重量パーセントの
Ｎ−メチルピロリドン溶液を作成し、配向剤１−５とし
た。[Example 1] A 10 weight percent N-methylpyrrolidone solution was prepared by mixing 2tli diamine having the following structural formula and tetracarboxylic acid anhydride in the proportions shown in Table 1, and was used as alignment agent 1-5.
尚、表の数値は重量割合を示す。Note that the numerical values in the table indicate weight percentages.
ジアミン１ ジアミン２ Ｈ、’Ｎ＋＠；＋ＪＨ。diamine 1 Diamine 2 H,'N+@;+JH.
テトラカルボン酸無水物Ｈ
表
ルク社製）を充填し、磁場配向法により液晶分子と基板
との角度を測定ｌまたところ表２の結果が得られた。The solution was filled with tetracarboxylic acid anhydride H (manufactured by Table Lux Co., Ltd.), and the angle between the liquid crystal molecules and the substrate was measured using a magnetic field alignment method.The results shown in Table 2 were obtained.
表 ２
これらの配向剤をスピンコード法により回転数１５００
ｒ ｐｍで透明電極付き基板に塗布した。Table 2 These alignment agents were rotated at a rotation speed of 1500 using the spin code method.
It was applied to a substrate with a transparent electrode at r pm.
この基板を９０度Ｃで２時間乾燥した後、２００度Ｃで
２時間焼成した。This substrate was dried at 90 degrees Celsius for 2 hours and then fired at 200 degrees Celsius for 2 hours.
焼成後、この基板を送り速度０．６メ一トル／分で、回
転数４００ｒｐｍで回転１．ている表面にナイロン繊維
が植毛されている直径８０ミリメートルの回転体の下を
移送し、ラビング処理をした。After firing, this substrate was rotated at a feed rate of 0.6 m/min and a rotational speed of 400 rpm for 1. The material was transferred under a rotating body with a diameter of 80 mm, the surface of which was flocked with nylon fibers, and subjected to a rubbing treatment.
このようにして得た基板をラビング方向が２２０度にな
るようにして、１２ミクロンのスペーサを介して液晶セ
ルを組立、液晶（Ｚｆ１２２１４メ尚、ジアミン１とテ
トラカルボン酸無水物３、ジアミン２とテトラカルボン
酸無水物３よりなる１０重量パーセントのＮ−メチルピ
ロリドン溶液を用いて同様の処理をし、ａＰＩ定した結
果はそれぞれ２０度と、２度であった。The rubbing direction of the thus obtained substrate was 220 degrees, and a liquid crystal cell was assembled via a 12 micron spacer. A similar treatment was performed using a 10 weight percent N-methylpyrrolidone solution containing tetracarboxylic anhydride 3, and the aPI values were determined to be 20 degrees and 2 degrees, respectively.
〔実施例２〕
次の構造式を有す２種のジアミンを表３の割合で混合し
た１０ｆｆｌｆｆｉパーセントのジメチルポルムアミド
溶液を作成し、配向剤６−１０とした。[Example 2] A 10ffffi percent dimethylpolamide solution was prepared by mixing two types of diamines having the following structural formulas in the proportions shown in Table 3, and used as an alignment agent 6-10.
尚、表の数値は重量割合を示す。Note that the numerical values in the table indicate weight percentages.
ジアミン４ ジアミン５ Ｈ２Ｎ ％ＣＨ２（Ｃ矢ＮＨ。Diamine 4 Diamine 5 H2N %CH2 (C arrow NH.
テトラカルボン酸無水物６
表 ３
度になるように１．て、１２ミクロンのスペーサを介し
て液晶セルを組立、液晶（ＺＬＩ２２１４メルク社製）
を充填し、磁場配向法により液晶分子と基板との角度を
測定したところ表４の結果が得られた。Tetracarboxylic anhydride 6 Table 3 degrees 1. Then, assemble the liquid crystal cell via a 12 micron spacer, and use the liquid crystal (ZLI2214 manufactured by Merck & Co., Ltd.)
When the angle between the liquid crystal molecules and the substrate was measured using a magnetic field alignment method, the results shown in Table 4 were obtained.
表 ４
これらの配向剤をスピンコード法により回転数２０００
ｒ ｐｍで透明電極トｊき基板に塗布した。Table 4 These alignment agents were rotated at a rotation speed of 2000 using the spin code method.
It was coated on a transparent electrode coated substrate at r.p.m.
この基板を９０度Ｃで２時間乾燥した後、２００度Ｃで
２時間焼成した。This substrate was dried at 90 degrees Celsius for 2 hours and then fired at 200 degrees Celsius for 2 hours.
焼成後、この基板を送り速度Ｏ２６メ一トル／分で、回
転数４０Ｏｒｐｍで回転している表面にナイロン繊維が
植毛されている直径８０ミリメートルの回転体の下を移
送し、ラビング処理をした。After firing, this substrate was transferred at a feed rate of 026 m/min under a rotating body having a diameter of 80 mm and having a surface covered with nylon fibers, which was rotating at a rotational speed of 40 rpm, and was subjected to a rubbing treatment.
このようにして得た基板をラビング方向が２２０尚、ジ
アミン４とテトラカルボン酸無水物６、ジアミン５とテ
トラカルボン酸無水物６より作成した１０重量パーセン
トのジメチルホルムアミド溶液を用いて同様の処理をし
、測定した結果それぞれ２２度と、４度であった。The substrate thus obtained was subjected to the same treatment using a 10% by weight dimethylformamide solution prepared from diamine 4 and tetracarboxylic anhydride 6 and diamine 5 and tetracarboxylic anhydride 6, with a rubbing direction of 220. However, the measured results were 22 degrees and 4 degrees, respectively.
以」二実施例を述べたが、本発明は上記実施例に限定さ
れるものではなく、広く、他の原料、溶媒、塗布条件、
乾燥、焼成条件においても適用出来るものである。Although two examples have been described below, the present invention is not limited to the above examples, and can be broadly applied to other raw materials, solvents, coating conditions,
It can also be applied under drying and firing conditions.
以上述べたように本発明によれば、液晶の種類、ネジレ
の角度等に合わせ配向剤を用意する必要がなく２種類ジ
アミンとテトラカルボン酸無水物を用意することにより
全てに対応出来るという効果を有する。As described above, according to the present invention, there is no need to prepare an alignment agent according to the type of liquid crystal, twist angle, etc., and by preparing two types of diamine and tetracarboxylic acid anhydride, it is possible to deal with all types. have
第１図は、液晶表示体の概念図である。 １１ ・ １２＠ １３・ １４ ・ ・基板 ・電極 ・配向膜 ・液晶 以 上 出願人 セイコーエプソン株式会社 FIG. 1 is a conceptual diagram of a liquid crystal display. 11・ 12@ 13. 14・ ·substrate ·electrode ・Alignment film ·liquid crystal Below Up Applicant: Seiko Epson Corporation
Claims (1)
サおよび液晶より成る液晶表示体用液晶セルにおいて、
下記構造式を有すジアミン化合物（１）、該化合物と異
なるジアミン系化合物（２）、テトラカルボン酸無水物
（３）を溶解した溶液を透明電極付き基板に塗布した後
、乾燥、焼成し、ラビング処理をすることを特徴とする
配向膜の作成方法。 ▲数式、化学式、表等があります▼ （但し、Ｒは水素叉はアルキル基を意味する。）[Claims] A liquid crystal cell for a liquid crystal display comprising a substrate with a transparent electrode, an alignment film coated on the substrate, a spacer, and a liquid crystal,
A solution containing a diamine compound (1) having the following structural formula, a diamine compound (2) different from the compound, and a tetracarboxylic anhydride (3) is applied to a substrate with a transparent electrode, and then dried and baked, A method for creating an alignment film characterized by performing a rubbing treatment. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, R means hydrogen or an alkyl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1045596A JP2780183B2 (en) | 1989-02-27 | 1989-02-27 | Alignment film and liquid crystal device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1045596A JP2780183B2 (en) | 1989-02-27 | 1989-02-27 | Alignment film and liquid crystal device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02223916A true JPH02223916A (en) | 1990-09-06 |
| JP2780183B2 JP2780183B2 (en) | 1998-07-30 |
Family
ID=12723733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1045596A Expired - Lifetime JP2780183B2 (en) | 1989-02-27 | 1989-02-27 | Alignment film and liquid crystal device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2780183B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103097947A (en) * | 2010-08-30 | 2013-05-08 | 夏普株式会社 | Liquid crystal display panel, liquid crystal display device, and polymer for alignment film material |
| KR20140026431A (en) | 2011-04-28 | 2014-03-05 | 닛산 가가쿠 고교 가부시키 가이샤 | Polyimide precursor modified with dicarboxylic acid anhydride, and imidized polyimide and liquid crystal alignment treatment agent comprising same |
| KR20190045258A (en) | 2016-08-30 | 2019-05-02 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element |
| KR20190045231A (en) | 2016-08-30 | 2019-05-02 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element using same |
| KR20190070331A (en) | 2016-10-14 | 2019-06-20 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element |
| US11111387B2 (en) | 2015-07-30 | 2021-09-07 | Nissan Chemical Industries, Ltd. | Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display element |
| KR20210143802A (en) | 2019-03-27 | 2021-11-29 | 닛산 가가쿠 가부시키가이샤 | Polymer composition, a liquid crystal aligning film, a liquid crystal display element, and the manufacturing method of the board|substrate which has a liquid crystal aligning film |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62174724A (en) * | 1986-01-29 | 1987-07-31 | Hitachi Ltd | Liquid crystal display element |
| JPS6378130A (en) * | 1986-09-22 | 1988-04-08 | Asahi Glass Co Ltd | Liquid crystal display element |
| JPS63262620A (en) * | 1987-04-21 | 1988-10-28 | Nissan Chem Ind Ltd | Orientation treating agent for liquid crystal display cell |
| JPS646923A (en) * | 1987-06-30 | 1989-01-11 | Sumitomo Bakelite Co | Liquid crystal display element |
-
1989
- 1989-02-27 JP JP1045596A patent/JP2780183B2/en not_active Expired - Lifetime
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62174724A (en) * | 1986-01-29 | 1987-07-31 | Hitachi Ltd | Liquid crystal display element |
| JPS6378130A (en) * | 1986-09-22 | 1988-04-08 | Asahi Glass Co Ltd | Liquid crystal display element |
| JPS63262620A (en) * | 1987-04-21 | 1988-10-28 | Nissan Chem Ind Ltd | Orientation treating agent for liquid crystal display cell |
| JPS646923A (en) * | 1987-06-30 | 1989-01-11 | Sumitomo Bakelite Co | Liquid crystal display element |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103097947A (en) * | 2010-08-30 | 2013-05-08 | 夏普株式会社 | Liquid crystal display panel, liquid crystal display device, and polymer for alignment film material |
| CN103097947B (en) * | 2010-08-30 | 2016-03-16 | 夏普株式会社 | Display panels, liquid crystal indicator and polymer for aligning film material |
| KR20140026431A (en) | 2011-04-28 | 2014-03-05 | 닛산 가가쿠 고교 가부시키 가이샤 | Polyimide precursor modified with dicarboxylic acid anhydride, and imidized polyimide and liquid crystal alignment treatment agent comprising same |
| US9447240B2 (en) | 2011-04-28 | 2016-09-20 | Nissan Chemical Industries, Ltd. | Polyimide precursor modified with dicarboxylic acid anhydride, imidized polyimide and liquid crystal aligning agent using it |
| JP2016210784A (en) * | 2011-04-28 | 2016-12-15 | 日産化学工業株式会社 | Novel dicarboxylic acid anhydride, and method for producing the same |
| US11111387B2 (en) | 2015-07-30 | 2021-09-07 | Nissan Chemical Industries, Ltd. | Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display element |
| KR20190045258A (en) | 2016-08-30 | 2019-05-02 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element |
| KR20190045231A (en) | 2016-08-30 | 2019-05-02 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element using same |
| KR20190070331A (en) | 2016-10-14 | 2019-06-20 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element |
| KR20210143802A (en) | 2019-03-27 | 2021-11-29 | 닛산 가가쿠 가부시키가이샤 | Polymer composition, a liquid crystal aligning film, a liquid crystal display element, and the manufacturing method of the board|substrate which has a liquid crystal aligning film |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2780183B2 (en) | 1998-07-30 |
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