JPS6363641A - Benzoic acid biphenyl ester derivative - Google Patents
Benzoic acid biphenyl ester derivativeInfo
- Publication number
- JPS6363641A JPS6363641A JP20651686A JP20651686A JPS6363641A JP S6363641 A JPS6363641 A JP S6363641A JP 20651686 A JP20651686 A JP 20651686A JP 20651686 A JP20651686 A JP 20651686A JP S6363641 A JPS6363641 A JP S6363641A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- liquid crystal
- benzoic acid
- biphenyl ester
- 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
- -1 Benzoic acid biphenyl ester Chemical class 0.000 title claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 11
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 235000010290 biphenyl Nutrition 0.000 abstract description 2
- 239000004305 biphenyl Substances 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-BYPYZUCNSA-N (S)-2-methylbutyric acid Chemical compound CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- JDCUQPSPITUXGL-UHFFFAOYSA-N 4-(4-octylphenyl)phenol Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=C(O)C=C1 JDCUQPSPITUXGL-UHFFFAOYSA-N 0.000 description 1
- 101150032866 CDC11 gene Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は、新規な液晶化合物を提供するものである０
本発明によって提供される液晶化合物は。[Detailed Description of the Invention] (Industrial Application Field) This invention provides a novel liquid crystal compound.
The liquid crystal compound provided by the present invention is:
強誘電性カイラルスメクチック液晶化合物であって、そ
れ自体で又は他の液晶化合物とブレンドして、電気光学
的効果を利用した液晶表示装置、オプティカルシャッタ
ー等、電気光学装置の作成に使用されるものである。A ferroelectric chiral smectic liquid crystal compound that is used by itself or blended with other liquid crystal compounds to create electro-optical devices such as liquid crystal displays and optical shutters that utilize electro-optic effects. be.
（従来の技術）
液晶化合物として数多く知られているものに、ネマチッ
ク液晶と呼ばれているものがある。このものは、現在、
液晶表示装置に使用されているものの主流をなしている
けれども、表示の大容量化に対しては限界に近づいてい
ると言われている。(Prior Art) Among the many known liquid crystal compounds, there is one called nematic liquid crystal. This one is currently
Although it is the mainstream used in liquid crystal display devices, it is said that it is approaching its limit in terms of increasing display capacity.
強誘電性液晶は、高速応答性とメモリ性を持っているた
め、次世代の液晶として注目を集め、盛んに研究されて
いる。その中に、（Ｓ）−２−メチルブチルｐ−（ｐ−
ｎ−デシロキシベンジリデンアミノ）シンナメート（Ｄ
ＯＢＡＭＢＣ）がよく知られた化合物としである。しか
し、この化合物は、液晶性を示す温度が６０℃以上とい
う高い温度であるため、使用に際して温度的制限を受け
る。Ferroelectric liquid crystals have high-speed response and memory properties, so they are attracting attention as next-generation liquid crystals and are being actively researched. Among them, (S)-2-methylbutyl p-(p-
n-decyloxybenzylidene amino) cinnamate (D
OBAMBC) is a well-known compound. However, since this compound exhibits liquid crystallinity at a high temperature of 60° C. or higher, its use is subject to temperature limitations.
室温を含む広い温度範囲で液晶性を示す強誘電性カイラ
ルスメクチック液晶を得るために、化合物それ自体の創
製あるいはブレンドによる性能の改善に多くの努力が払
われている０例えば、温度範囲を広げるため、或いは液
晶材料ができるだけ均一なドメインを呈するようにする
ため種々材料の添加が試みられている。In order to obtain ferroelectric chiral smectic liquid crystals that exhibit liquid crystallinity over a wide temperature range including room temperature, many efforts have been made to improve the performance by creating the compound itself or by blending it. For example, to widen the temperature range. Alternatively, attempts have been made to add various materials in order to make the liquid crystal material exhibit domains as uniform as possible.
（解決しようとする問題点）
本発明は、式（１）
（式中、Ｒ工はＣ２〜Ｃ１のアルキル基を、Ｒ２はＣ３
〜Ｃ１□の直鎖アルキル又はアルコキシ基を、＊印は該
炭素原子が不斉炭素原子であることを示す、）
で示される新規なカイラルスメクチック液晶化合物を提
供せんとするものであり、提供される液晶化合物は、他
の強誘電性カイラルスメクチック液晶にブレンドすれば
ドメイン性を良好にすると共にスメクチックＣ相を呈す
る温度範囲を拡げる働きをする。(Problems to be Solved) The present invention solves the problem of the formula (1) (wherein, R represents a C2-C1 alkyl group, R2 represents a C3
It is an object of the present invention to provide a novel chiral smectic liquid crystal compound represented by a linear alkyl or alkoxy group of ~C1□, where the * mark indicates that the carbon atom is an asymmetric carbon atom. When blended with other ferroelectric chiral smectic liquid crystals, the liquid crystal compound improves domain properties and works to expand the temperature range in which the smectic C phase is exhibited.
（問題点を解決するための手段）
本発明によって提供される新規な強誘電性カイラルスメ
クチック液晶化合物は、次のようにして造られる。即ち
、式（１１）
（式中Ｒ２は、前記と同じ）
で示される化合物と式（ＩＩＩ）
（式中Ｒ□は、前記と同じ）
で示される化合物又はその反応性誘導体とを反応させる
ことによって造ることができる。(Means for Solving the Problems) The novel ferroelectric chiral smectic liquid crystal compound provided by the present invention is produced as follows. That is, reacting a compound represented by formula (11) (wherein R2 is the same as above) with a compound represented by formula (III) (wherein R□ is the same as above) or a reactive derivative thereof. It can be built by.
ここにおいて式（ＩＩ）で示される化合物における置換
基Ｒ２としてはペンチル、ヘキシル、ヘプチル、オクチ
ル、ノニル、デシル、ウンデシル、ドデシル、ペンチル
オキシ、ヘキシルオキシ、ヘプチルオキシ、オクチルオ
キシ、ノニルオキシ、デシルオキシ、ウンデシルオキシ
、ドデシルオキシ、などが挙げられ、一方、式（ｍ）で
示される化合物における置換基Ｒ１としてはエチル、プ
ロピル、ブチル、ペンチル、などが挙げられる。Here, as the substituent R2 in the compound represented by formula (II), pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyl Examples of the substituent R1 in the compound represented by formula (m) include oxy, dodecyloxy, and the like, while examples of the substituent R1 in the compound represented by formula (m) include ethyl, propyl, butyl, pentyl, and the like.
反応は適宜溶媒中縮合剤の存在又は不存在で進められる
。用いられる溶媒としては、酢酸エチル、ベンゼン、ト
ルエン、キシレン、エチルエーテル、イソプロピルエー
テル、ヘキサン、ジグリム、ジメチルホルムアミドなど
が挙げられ、縮合剤としてはジシクロへキシルカルボジ
イミド、オキシ塩化燐、塩化チオニルなどが挙げられる
０式（’ＩＩ［）で示される化合物の反応性誘導体用い
る場合における反応性誘導体としては、酸ハライド、混
合酸無水物、活性エステルなどが挙げられる。The reaction is carried out in a solvent in the presence or absence of a condensing agent, as appropriate. Examples of the solvent used include ethyl acetate, benzene, toluene, xylene, ethyl ether, isopropyl ether, hexane, diglyme, dimethylformamide, etc., and condensing agents include dicyclohexylcarbodiimide, phosphorus oxychloride, thionyl chloride, etc. Reactive derivatives of the compound represented by formula ('II[)] include acid halides, mixed acid anhydrides, active esters, and the like.
用いられる原料化合物（ＩＩ）及び（ＩＩＩ）は次のよ
うにして造られる。The raw material compounds (II) and (III) used are produced as follows.
ＨＯつ℃
（Ｍ）
（式中Ｒ，Ｒ’、はアルキル基を示す）（式中Ｒ工は前
記と同じ）
ＣＨ。HO℃ (M) (In the formula, R and R' represent an alkyl group) (In the formula, R is the same as above) CH.
尚 ＲニーＣＨ−ＣＯＯＩ−Ｉは光学的に活性な酸、→
ト
例えば（Ｓ）−（＋）−２−メチル酪酸を使用、又はβ
−オキシイソ酪酸を原料にして常法に従い誘導される各
種誘導体が挙げられる。In addition, R-CH-COOI-I is an optically active acid, →
For example, using (S)-(+)-2-methylbutyric acid, or β
Examples include various derivatives derived from -oxyisobutyric acid according to conventional methods.
以下実施例を記述して本発明を具体的に説明する。The present invention will be specifically explained below by describing examples.
実施例
す
（Ｓ） −４−（２−メチルブチールオキシ）安息６
酸４ ’ （４” ｎ−オクチル）ビフェニルエ
ステル
１．３ｇ （０，００３９ｍｏ ｌ）の（Ｓ） −４−
（２−メチルブチニルオキシ）安息香酸、１゜６５ｇ
（０，００５８ｍｏｌ）の４−ヒドロキシ−４’−ｎ−
オクチルビフェニル、１．３ｇ（０゜００６３ｍｏ １
）のＮ、Ｎ’ −ジシクロへキシルカルボジイミド及び
０．０’７ｇ （０，ＯＯ０５１ｍｏ１）の４−ジメナ
ルアミノピリジンを、２０ｍ１の酢酸エチル中で室温で
１５時間攪はんした。Example (S) -4-(2-methylbutyloxy)benzo 6
(S)-4- of acid 4′ (4” n-octyl)biphenyl ester 1.3 g (0,0039 mol)
(2-methylbutynyloxy)benzoic acid, 1°65g
(0,0058 mol) of 4-hydroxy-4'-n-
Octylbiphenyl, 1.3g (0°0063mo 1
) N,N'-dicyclohexylcarbodiimide and 0.0'7 g (0,OO051 mol) of 4-dimenalaminopyridine were stirred in 20 ml of ethyl acetate at room temperature for 15 hours.
終了後、氷水にあけ、酢酸エチルで抽出し、水洗いし、
硫酸マグネシウムで乾燥後、濃縮した。これをシリカゲ
ルカラムクロマトグラフィー及び二タノール再結晶によ
り精表を行い、０．８ ｇの題記化合物を得た。After finishing, pour into ice water, extract with ethyl acetate, wash with water,
After drying with magnesium sulfate, it was concentrated. This was purified by silica gel column chromatography and ditanol recrystallization to obtain 0.8 g of the title compound.
［αヴ＝＋１０．４°（Ｃ＝ ２．１３ 、 ＣＨＣ１
，）ＩＲ’ｖ−ａ、、ｅｘ、 １７６０． １７４
０゜’ＨＮＭＲ（６０ＭＩＩｚ、ＣＤＣ１１）δ （ｐ
ｐｍ）： ０．６０〜２．００ （ｍ、２３Ｈ）２．３
３〜２．８３（ｍ、 ３Ｈ）
７、 ００〜７． ７３ （ｍ、 １０）Ｔ）８．
１７ （ｄ、 ２Ｈ）得られた
化合物の相転移温度を以下に記す。[αV=+10.4°(C=2.13, CHC1
,) IR'v-a,, ex, 1760. 174
0゜'HNMR (60MIIz, CDC11) δ (p
pm): 0.60-2.00 (m, 23H) 2.3
3-2.83 (m, 3H) 7, 00-7. 73 (m, 10)T)8.
17 (d, 2H) The phase transition temperature of the obtained compound is described below.
Ｃｒｙ −５ｘ−４３ｙ−ｋＳｚ−４Ｓｃ” →Ｃｈ
→Ｉｓ。Cry -5x-43y-kSz-4Sc” →Ch
→Is.
（Ｓｘ、 Ｓｙ、 Ｓ２は、相未同定のスメクチック相
）この化合物を以下に示した強誘電性液晶組成物Ａにブ
レンドしたときの特性の比較を表に示す。(Sx, Sy, S2 are unidentified smectic phases) A comparison of properties when this compound is blended with ferroelectric liquid crystal composition A shown below is shown in the table.
ここで応答速度は、１．７ μｍのセルに封入し、±２
０Ｖのパルス波形を印加し、表示が切りかわる最小のパ
ルス巾として求めた。Here, the response speed is ±2 when sealed in a 1.7 μm cell.
A 0V pulse waveform was applied, and the minimum pulse width at which the display changed was determined.
表に示したように、組成物Ａに実施例の化合物を適量ブ
レンドすることにより、Ｓｃ”相の温度域を上下に広げ
ることが出来、かつ応答性を改善することが出来た。As shown in the table, by blending Composition A with an appropriate amount of the compound of Example, it was possible to expand the temperature range of the Sc'' phase and improve the response.
Claims (1)
２はＣ＿５〜Ｃ＿１＿２の直鎖アルキル又はアルコキシ
基を、＊印は該炭素原子が不斉炭素原子であることを示
す。） で示される安息香酸ビフェニルエステル誘導体[Claims] Formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 represents an alkyl group of C_2 to C_5, R_
2 represents a linear alkyl or alkoxy group of C_5 to C_1_2, and the * mark indicates that the carbon atom is an asymmetric carbon atom. ) Benzoic acid biphenyl ester derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20651686A JPH0735353B2 (en) | 1986-09-02 | 1986-09-02 | Benzoic acid biphenyl ester derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20651686A JPH0735353B2 (en) | 1986-09-02 | 1986-09-02 | Benzoic acid biphenyl ester derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6363641A true JPS6363641A (en) | 1988-03-22 |
| JPH0735353B2 JPH0735353B2 (en) | 1995-04-19 |
Family
ID=16524657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20651686A Expired - Fee Related JPH0735353B2 (en) | 1986-09-02 | 1986-09-02 | Benzoic acid biphenyl ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0735353B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01252938A (en) * | 1988-03-31 | 1989-10-09 | Matsushita Electric Ind Co Ltd | Ferroelectric liquid crystal panel |
| JPH01254793A (en) * | 1988-04-01 | 1989-10-11 | Matsushita Electric Ind Co Ltd | Ferroelectric liquid crystal composition |
-
1986
- 1986-09-02 JP JP20651686A patent/JPH0735353B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01252938A (en) * | 1988-03-31 | 1989-10-09 | Matsushita Electric Ind Co Ltd | Ferroelectric liquid crystal panel |
| JPH01254793A (en) * | 1988-04-01 | 1989-10-11 | Matsushita Electric Ind Co Ltd | Ferroelectric liquid crystal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0735353B2 (en) | 1995-04-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |