JPS6366825B2 - - Google Patents
Info
- Publication number
- JPS6366825B2 JPS6366825B2 JP3916681A JP3916681A JPS6366825B2 JP S6366825 B2 JPS6366825 B2 JP S6366825B2 JP 3916681 A JP3916681 A JP 3916681A JP 3916681 A JP3916681 A JP 3916681A JP S6366825 B2 JPS6366825 B2 JP S6366825B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- trans
- liquid crystal
- chloro
- group
- 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.)
- Expired
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- 239000004973 liquid crystal related substance Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 11
- -1 3-chloro-4-cyanophenyl ester Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 7
- VACLULPMEXHBMD-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzoic acid Chemical compound C1CC(CCC)CCC1C1=CC=C(C(O)=O)C=C1 VACLULPMEXHBMD-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- BDDVAWDNVWLHDQ-UHFFFAOYSA-N 2-chloro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(Cl)=C1 BDDVAWDNVWLHDQ-UHFFFAOYSA-N 0.000 description 2
- XVROSBHWACAQRL-UHFFFAOYSA-N 4-(4-heptylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 XVROSBHWACAQRL-UHFFFAOYSA-N 0.000 description 2
- VRGQQLFRUKMDSW-UHFFFAOYSA-N 4-(4-pentylphenyl)benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 VRGQQLFRUKMDSW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は正の誘電異方性値の大きい新規な液晶
化合物及びそれを含有する液晶組成物に関する。
液晶表示素子は液晶物質が有する光学異方性及
び誘電異方性を利用したものであるが、その表示
方式にはTN型（ねじれネマチツク型）、DS型
（動的散乱型）、ゲスト・ホスト型、DAP型、ホ
ワイト・テイラー型など各種の方式があり、それ
ぞれの方式により使用される液晶物質に要求され
る性質も異る。例えば表示素子の種類によつて、
液晶物質として誘電異方性△εが正のものを必要
としたり、負のものを必要としたり、或はその中
間的な値のものが適したりする。しかしいずれに
しても使用される液晶物質はできるだけ広い温度
範囲で液晶相を示し、又水分、熱、空気、光など
に対して安定である必要がある。現在のところ単
一化合物でこの様な条件をすべて満たすものはな
く、数種の液晶化合物や非液晶化合物を混合して
一応実用に耐えるものを得ているのが現状であ
る。
最近、特に低電圧で駆動出来る液晶表示素子に
対する要求が高まり、その様な要求を充たすため
には通常△εの大きい液晶組成物が必要となる。
一般的に任意の△ε値を持つ液晶組成物は△ε
値が正の化合物と負の化合物を適宜混合すること
によつて得られる。従つて△ε値の大きい液晶組
成物を得るには△ε値の出来るだけ大きい成分を
使用すればよい訳だが、その場合他の成分との相
溶性がよく、かつ得られる組成物の液晶温度範囲
を広げるか少くともせばめない様な物でなければ
ならない。本発明の化合物は上記の様な目的に使
用して有用な正の誘電異方性値の大きい新規な液
晶化合物である。
即ち本発明は一般式
（上式中、Ｒは炭素数１〜10を有するアルキル基
を示し、
The present invention relates to a novel liquid crystal compound having a large positive dielectric anisotropy value and a liquid crystal composition containing the same. Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and display methods include TN type (twisted nematic type), DS type (dynamic scattering type), and guest/host type. There are various types of liquid crystals, such as type, DAP type, and White-Taylor type, and each type requires different properties of the liquid crystal material used. For example, depending on the type of display element,
As a liquid crystal material, a material with a positive dielectric anisotropy Δε is required, a material with a negative dielectric anisotropy is required, or a material with an intermediate value is suitable. However, in any case, the liquid crystal material used must exhibit a liquid crystal phase over as wide a temperature range as possible and be stable against moisture, heat, air, light, etc. At present, there is no single compound that satisfies all of these conditions, and the current state of affairs is to mix several types of liquid crystal compounds and non-liquid crystal compounds to obtain compounds that can withstand practical use. Recently, there has been an increasing demand for liquid crystal display elements that can be driven particularly at low voltages, and in order to meet such demands, liquid crystal compositions with a large Δε are usually required. In general, a liquid crystal composition with an arbitrary △ε value is △ε
It is obtained by appropriately mixing a compound with a positive value and a compound with a negative value. Therefore, in order to obtain a liquid crystal composition with a large Δε value, it is sufficient to use a component with a Δε value as large as possible. It must be something that expands the range or at least does not narrow it down. The compound of the present invention is a novel liquid crystal compound with a large positive dielectric anisotropy value useful for the above-mentioned purposes. That is, the present invention is based on the general formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms,
【式】は１，４
−フエニレン基又はトランス−１，４−シクロヘ
キシレン基を示す）
で表わされるカルボン酸の３−クロロ−４−シア
ノフエニルエステルである。
本発明の（）式の化合物は誘電異方性値が＋
30程度と大きく、かつ広い温度範囲で液晶相を示
すので△ε値が大きくかつ広い液晶温度範囲をも
つ液晶組成物を構成する成分として好適なもので
ある。
つぎに本発明の（）式の化合物の製造法を示
す。まず目的とする最終化合物に対応する置換カ
ルボン酸を塩化チオニルなどで置換カルボン酸ク
ロリドとし、ついで３−クロロ−４−シアノフエ
ノールとピリジン存在下で反応すれば目的の置換
カルボン酸の３−クロロ−４−シアノフエニルエ
ステルが得られる。化学反応式で示すと
以下実施例により本化合物の製造法、及びそれ
を含む組成物につき更に詳細に説明する。
実施例 １
〔４−（トランス−4′−プロピルシクロヘキシ
ル）安息香酸3″−クロロ−4″−シアノフエニル
エステル（（）式でＲがC3H7、
[Formula] represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group) 3-chloro-4-cyanophenyl ester of a carboxylic acid. The compound of formula () of the present invention has a dielectric anisotropy value of +
Since it has a large Δε value of about 30 and exhibits a liquid crystal phase over a wide temperature range, it is suitable as a component for a liquid crystal composition having a large Δε value and a wide liquid crystal temperature range. Next, a method for producing the compound of formula () of the present invention will be described. First, a substituted carboxylic acid corresponding to the desired final compound is converted into a substituted carboxylic acid chloride using thionyl chloride, etc., and then reacted with 3-chloro-4-cyanophenol in the presence of pyridine to form the desired substituted carboxylic acid. 4-cyanophenyl ester is obtained. Shown as a chemical reaction formula: The method for producing the present compound and the composition containing the same will be explained in more detail with reference to Examples below. Example 1 [4-(trans-4'-propylcyclohexyl)benzoic acid 3''-chloro-4''-cyanophenyl ester (in the formula (), R is C3H7 ,
【式】がトランス−１，４−シクロヘ キシレン基、[Formula] is trans-1,4-cyclohe xylene group,
【式】が１，４−フエニ
レン基のもの）の製造〕
４−（トランス−4′−プロピルシクロヘキシル）
安息香酸5.0ｇ（0.02モル）と塩化チオニル20ml
をフラスコに入れ、湯浴上80℃で還流すると３時
間で完全に均一になる。過剰の塩化チオニルを減
圧で留去すると酸クロリドが残留物として得られ
る。一方、別のフラスコに３−クロロ−４−シア
ノフエノール3.7ｇ（0.02モル）をピリジン10ml
にとかしておき、よく振りまぜながら先の酸クロ
リドを加えると反応して沈澱が生ずる。そのまま
一晩放置した後、水100mlにあけ、トルエン50ml
で２回抽出し、そのトルエン層を6N塩酸、つい
で2N苛性ソーダ水溶液で洗浄後、トルエン層が
中性になるまで水洗する。ついで硫酸ナトリウム
で乾燥後、減圧にてトルエンを留去すると目的の
化合物の粗製結晶物が残る。これをエタノールで
２回再結晶すると粗製された目的物の結晶が5.5
ｇ得られた（収率75％）。このものの融点Ｃ−Ｎ
点は99.4〜100.0℃、Ｎ−点は147.5℃であつた。
実施例 ２〜５
実施例１における４−（トランス−4′−プロピ
ルシクロヘキシル）安息香酸の代りに他のアルキ
ル基を持つた４−（トランス−4′−アルキルシク
ロヘキシル）安息香酸の0.02モル使用する以外は
全く同様にして第１表の実施例２〜５の欄に示す
（）式の化合物を得た。その物性値は第１表に
示す通りである。[Formula] is 1,4-phenylene group] Production of 4-(trans-4'-propylcyclohexyl)
5.0 g (0.02 mol) of benzoic acid and 20 ml of thionyl chloride
Pour into a flask and reflux at 80°C on a water bath until it becomes completely homogeneous in 3 hours. Excess thionyl chloride is distilled off under reduced pressure to obtain the acid chloride as a residue. Meanwhile, in another flask, add 3.7 g (0.02 mol) of 3-chloro-4-cyanophenol to 10 ml of pyridine.
When the above acid chloride is added to the mixture while stirring well, a reaction occurs and a precipitate is formed. After leaving it overnight, pour into 100ml of water and add 50ml of toluene.
The toluene layer is washed with 6N hydrochloric acid, then with 2N aqueous sodium hydroxide solution, and then with water until the toluene layer becomes neutral. After drying over sodium sulfate, the toluene is distilled off under reduced pressure to leave a crude crystal of the desired compound. When this is recrystallized twice with ethanol, the crude target product crystals are 5.5
g (yield 75%). Melting point of this substance C-N
The point was 99.4-100.0°C, and the N-point was 147.5°C. Examples 2 to 5 0.02 mol of 4-(trans-4'-alkylcyclohexyl)benzoic acid having another alkyl group was used instead of 4-(trans-4'-propylcyclohexyl)benzoic acid in Example 1. Compounds of formula () shown in the columns of Examples 2 to 5 in Table 1 were obtained in exactly the same manner except for the above. Its physical property values are shown in Table 1.
【表】
実施例 ６
実施例１に於ける４−（トランス−4′−プロピ
ルシクロヘキシル）安息香酸の代りに4′−ペンチ
ルビフエニル−４−カルボン酸5.4ｇ（0.02モル）
を使用する以外は全く同様にして4′−ペンチルビ
フエニル−４−カルボン酸3′−クロロ−4″−シア
ノフエニルエステルを6.5ｇ得た（収率84％）。そ
の物性値も第１表に示す。
実施例 ７
実施例１に於ける４−（トランス−4′−プロピ
ルシクロヘキシル）安息香酸の代りに4′−ヘプチ
ルビフエニル−４−カルボン酸6.0ｇ（0.02モル）
を使用する以外は全く同様にして4′−ヘプチルビ
フエニル−４−カルボン酸3″−クロロ−4″−シア
ノフエニルエステル6.8ｇを得た（収率82％）。そ
の物性値も第１表に示す。
実施例 ８
実施例１に於ける４−（トランス−4′−プロピ
ルシクロヘキシル）安息香酸の代りにトランス−
４−（トランス−4′−ペンチルシクロヘキシル）
シクロヘキサンカルボン酸5.6ｇ（0.02モル）を
使用する以外は全く同様にしてトランス−４−
（トランス−4′−ペンチルシクロヘキシル）シク
ロヘキサンカルボン酸3″−クロロ−4″−シアノフ
エニルエステルを5.8ｇ得た（収率73％）。この物
性値も第１表に示す。
実施例 ９（使用例）
トランス−４−プロピル−（4′−シアノフエニ
ル）シクロヘキサン28％
トランス−４−ペンチル−（4′−シアノフエニ
ル）シクロヘキサン42％
トランス−４−ペンチル−（4′−シアノフエニ
ル）シクロヘキサン30％
の３成分からなるネマチツク液晶組成物のネマチ
ツク温度範囲は−３〜52℃で、△εは＋10.5、し
きい値電圧は1.53V、飽和電圧は2.12V、又20℃
での粘度は23cpである。
この液晶組成物85部に本発明の４−（トランス
−４−プロピルシクロヘキシル）安息香酸3″−ク
ロロ−4″−シアノフエニルエステル（実施例１）
15部を加えて得られた液晶組成物のネマチツク液
晶温度範囲は−５〜60.6℃に広がり、誘電異方性
値は＋13.8と大きくなり、しきい電圧は1.38V、
飽和電圧は1.88Vと夫々低下した。20℃での粘度
は34.8cpと上昇したが実用上大きな障害とならな
い範囲である。
以上の如く本発明の化合物を使用することによ
り表示素子の作動電圧を下げることが出来、又作
動温度範囲も広げることが出来た。[Table] Example 6 4'-pentylbiphenyl-4-carboxylic acid 5.4 g (0.02 mol) in place of 4-(trans-4'-propylcyclohexyl)benzoic acid in Example 1
6.5 g of 4'-pentylbiphenyl-4-carboxylic acid 3'-chloro-4''-cyanophenyl ester was obtained (yield 84%) in exactly the same manner except that It is shown in the table. Example 7 4'-heptylbiphenyl-4-carboxylic acid 6.0 g (0.02 mol) in place of 4-(trans-4'-propylcyclohexyl)benzoic acid in Example 1
6.8 g of 4'-heptylbiphenyl-4-carboxylic acid 3''-chloro-4''-cyanophenyl ester was obtained (yield: 82%). Its physical property values are also shown in Table 1. Example 8 In place of 4-(trans-4'-propylcyclohexyl)benzoic acid in Example 1, trans-
4-(trans-4'-pentylcyclohexyl)
Trans-4-
5.8 g of (trans-4'-pentylcyclohexyl)cyclohexanecarboxylic acid 3''-chloro-4''-cyanophenyl ester was obtained (yield 73%). The physical property values are also shown in Table 1. Example 9 (Usage example) Trans-4-propyl-(4'-cyanophenyl)cyclohexane 28% Trans-4-pentyl-(4'-cyanophenyl)cyclohexane 42% Trans-4-pentyl-(4'-cyanophenyl)cyclohexane The nematic temperature range of the 30% three-component nematic liquid crystal composition is -3 to 52°C, Δε is +10.5, threshold voltage is 1.53V, saturation voltage is 2.12V, and 20°C.
The viscosity at is 23 cp. 4-(trans-4-propylcyclohexyl)benzoic acid 3''-chloro-4''-cyanophenyl ester of the present invention (Example 1) was added to 85 parts of this liquid crystal composition.
The nematic liquid crystal temperature range of the liquid crystal composition obtained by adding 15 parts expanded from -5 to 60.6°C, the dielectric anisotropy value increased to +13.8, the threshold voltage was 1.38V,
The saturation voltage decreased to 1.88V. The viscosity at 20°C increased to 34.8 cp, but it was within a range that would not pose a major problem in practical use. As described above, by using the compound of the present invention, the operating voltage of the display element could be lowered, and the operating temperature range could also be expanded.
Claims (1)
示し、【式】【式】はいずれも １，４−フエニレン基又はトランス−１，４−ヘ
キシレン基を示す） で表わされるカルボン酸の３−クロロ−４−シア
ノフエニルエステル。 ２ 一般式 （上式中Ｒは炭素数１〜10を有するアルキル基を
示す） で表わされる４−（トランス−4′−アルキルシク
ロヘキシル）安息香酸3″−クロロ−4″−シアノフ
エニルエステルであるところの特許請求の範囲第
１項記載の化合物。 ３ 一般式 （上式中、Ｒは炭素数１〜10を有するアルキル基
を示す） で表わされる4′−置換ビフエニルカルボン酸3″−
クロロ−4″−シアノフエニルエステルである特許
請求の範囲第１項記載の化合物。 ４ 一般式 （上式中、Ｒは炭素数１〜10を有するアルキル基
を示す） で表わされるトランス−４−（トランス−4′−ア
ルキルシクロヘキシル）シクロヘキサンカルボン
酸3″−クロロ−4″−シアノフエニルエステルであ
る特許請求の範囲第１項記載の化合物。 ５ 一般式 （上式中、Ｒは炭素数１〜10を有するアルキル基
又はアルコキシ基を示し、【式】 【式】はいずれも１，４−フエニレン基 又はトランス−１，４−シクロヘキシレン基を示
す） で表わされるカルボン酸の３−クロロ−４−シア
ノフエニルエステルを少くとも１種含有すること
を特徴とする液晶組成物。[Claims] 1. General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms, [Formula] and [Formula] both represent a 1,4-phenylene group or a trans-1,4-hexylene group) 3-chloro-4-cyanophenyl ester of. 2 General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms.) A compound according to claim 1. 3 General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) 4'-substituted biphenylcarboxylic acid 3''-
The compound according to claim 1, which is chloro-4″-cyanophenyl ester. 4 General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) trans-4-(trans-4'-alkylcyclohexyl)cyclohexanecarboxylic acid 3''-chloro-4''-cyanophenyl ester The compound according to claim 1, which is 5 General formula (In the above formula, R represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms, and [Formula] and [Formula] each represent a 1,4-phenylene group or a trans-1,4-cyclohexylene group) 1. A liquid crystal composition comprising at least one 3-chloro-4-cyanophenyl ester of carboxylic acid represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3916681A JPS57154158A (en) | 1981-03-18 | 1981-03-18 | Liquid crystal substance having large positive dielectric anisotropy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3916681A JPS57154158A (en) | 1981-03-18 | 1981-03-18 | Liquid crystal substance having large positive dielectric anisotropy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57154158A JPS57154158A (en) | 1982-09-22 |
| JPS6366825B2 true JPS6366825B2 (en) | 1988-12-22 |
Family
ID=12545531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3916681A Granted JPS57154158A (en) | 1981-03-18 | 1981-03-18 | Liquid crystal substance having large positive dielectric anisotropy |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57154158A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0685068B2 (en) * | 1990-06-21 | 1994-10-26 | イーストマン・コダック・カンパニー | Film pack disposable camera and printed circuit board assembly used therefor |
| JP2897703B2 (en) * | 1995-12-20 | 1999-05-31 | 富士写真フイルム株式会社 | Film unit with lens |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019665B2 (en) * | 1979-05-28 | 1987-12-16 | MERCK PATENT GmbH | Liquid-crystal compositions |
| JPS5817414A (en) * | 1981-07-24 | 1983-02-01 | Seiko Epson Corp | Liquid crystal optical device |
| GB2114994B (en) * | 1982-02-18 | 1984-10-10 | Suwa Seikosha Kk | Liquid crystal compositions |
| US4502974A (en) * | 1982-03-31 | 1985-03-05 | Chisso Corporation | High temperature liquid-crystalline ester compounds |
| US4548731A (en) * | 1982-05-17 | 1985-10-22 | Chisso Corporation | 2,4-Difluorobenzene derivatives |
| US4424371A (en) * | 1982-09-23 | 1984-01-03 | Timex Corporation | 3-Chloro-4-cyanophenyl 4'-substituted benzoates |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| GB2132192B (en) * | 1982-10-30 | 1986-01-22 | Dainippon Ink & Chemicals | Nematic liquid crystalline 3-fluro-4-cyanophenol derivatives |
| JPS59170053A (en) * | 1983-03-18 | 1984-09-26 | Dainippon Ink & Chem Inc | 3-fluoro-4-cyanophenol derivative |
| JPS59128367A (en) * | 1983-01-10 | 1984-07-24 | Chisso Corp | Cyanophenyl ester derivative |
| CH660003A5 (en) * | 1984-04-16 | 1987-03-13 | Merck Patent Gmbh | ANISOTROPE COMPOUNDS AND FK MIXTURES WITH THESE. |
| JPH0825957B2 (en) * | 1985-03-12 | 1996-03-13 | チッソ株式会社 | Difluoro aromatic compound |
-
1981
- 1981-03-18 JP JP3916681A patent/JPS57154158A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0685068B2 (en) * | 1990-06-21 | 1994-10-26 | イーストマン・コダック・カンパニー | Film pack disposable camera and printed circuit board assembly used therefor |
| JP2897703B2 (en) * | 1995-12-20 | 1999-05-31 | 富士写真フイルム株式会社 | Film unit with lens |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57154158A (en) | 1982-09-22 |
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