JPS6254783B2 - - Google Patents
Info
- Publication number
- JPS6254783B2 JPS6254783B2 JP58152526A JP15252683A JPS6254783B2 JP S6254783 B2 JPS6254783 B2 JP S6254783B2 JP 58152526 A JP58152526 A JP 58152526A JP 15252683 A JP15252683 A JP 15252683A JP S6254783 B2 JPS6254783 B2 JP S6254783B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- substituted
- point
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000004988 Nematic liquid crystal Substances 0.000 description 8
- 230000007704 transition Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 cyclohexanecarboxylic acid biphenyl ester Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- BNPWVUJOPCGHIK-UHFFFAOYSA-N 3,4-difluorophenol Chemical compound OC1=CC=C(F)C(F)=C1 BNPWVUJOPCGHIK-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical class C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LIDDQKAMUXHIQD-UHFFFAOYSA-N phenyl 2-benzoyloxybenzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 LIDDQKAMUXHIQD-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
本発明は電気光学的表示材料として有用な３・
４−ジフルオロフエノール誘導体の新規ネマチツ
ク液晶化合物に関する。本発明によつて提供され
る新規ネマチツク液晶化合物は
一般式
〔式中、Ｒは炭素原子数１〜９の直鎖状アルキル
基を表わし２つのシクロヘキサン環の配置はそれ
ぞれトランス（エカトリアル−エカトリアル）配
置である。〕
で表わされる化合物である。
液晶表示セルの代表的なものにエム・シヤツト
（Ｍ・Schadt）等〔APPLIED PHYSICS
LETTERS 18、127〜128（1971）〕によつて提
案された電界効果型セル（フイールド・エフエク
ト・モード・セル）又はジー・エイチ・ハイルマ
イヤー（Ｇ・Ｈ Heilmeier）等
〔PROCEEDING OF THE I.E.E.E. 56 1162
〜1171（1968）〕によつて提案された動的光散型
セル（ダイミツク・スキヤツタリング・モード・
セル）又はジー・エイチ・ハイルマイヤー（Ｇ・
Ｈ Heilmeier）等〔APPLIED PHYSICS
LETTERS 13 91（1968）〕あるいはデイー・
エル・ホワイト（Ｄ Ｌ White）等
〔JOURNAL OF APPLIED PHYSICS 45、
4718（1974）〕によつて提案されたゲスト・ホス
ト型セルなどがある。
これらの液晶表示セルに用いられる液晶材料に
は種々の特性が要求されるが、室温を含む広い温
度範囲でネマチツク相を有することは各種表示セ
ルに共通して要求されている重要な特性である。
このような特性を有する実用可能な材料の多く
は、通常、室温付近にネマチツク相を有する化合
物と室温より高い温度領域にネマチツク相を有す
る化合物から成る数種又はそれ以上の成分を混合
することによつて調製される。現在実用的に使用
される上記の如き混合液晶の多くは、少なくとも
−30℃〜＋65℃の全温度範囲に亘つてネマチツク
相を有することが要求されている。かかる要求を
満すために、室温より高い温度領域にネマチツク
相を有する化合物として、４・4′−置換ターフエ
ニル、４・4′−置換ビフエニルシクロヘキサン、
４・4′−置換ベンゾイルオキシ安息香酸フエニル
エステルの如き、約100℃の結晶相−ネマチツク
相転移温度（Ｃ−Ｎ点）を有すると共に約200℃
のネマチツク相−等方性液体相転移温度（Ｎ−Ｉ
点）を有する化合物が使用される場合が多い。し
かしながら、これらの化合物は、混合液晶のＮ−
Ｉ点を65℃又はそれ以上の温度とするのに充分な
量を混合した場合、得られる混合液晶の粘度を上
昇せしめ、このことによつて応答速度を低下せし
める好ましからざる性質を有している。さらに電
界効果型セル特にTN型セルに用いられる液晶材
料に要求される特性の一つに低電圧動作性があ
る。一般に液晶表示セルの動作電圧を下げること
は液晶のしきい値電圧Vthを下げることに対応す
る。上記のごとき高いＮ−Ｉ点を有する化合物
は、混合液晶のＮ−Ｉ点を65℃又はそれ以上の温
度とするのに充分な量を混合した場合、得られる
混合液晶のしきい値電圧を上昇せしめ、このこと
によつて動作電圧を上げてしまう好ましからざる
性質を有している。
本発明に係る式（）の化合物は、この性質が
改良された新規な化合物である。即ち、式（）
の化合物は、他の１種又は２種以上のネマチツク
液晶化合物と混合することによつて65℃以上のＮ
−Ｉ点を有する実用可能な混合液晶を調製する
際、前記公知の液晶化合物が粘度及びしきい値電
圧の両方あるいはどちらか一方を著しく上昇せし
めてしまうのに対し、混合液晶の粘度及びしきい
値電圧の上昇を小幅に抑えることができる。
更に、式（）の化合物は、本出願人が特開昭
54−83694号公報の中で時分割駆動特性の優れた
ネマチツク液晶材料として報告した４・4′−置換
シクロヘキシルカルボン酸フエニルエステルと極
めて良好な相溶性を有するから、これらの化合物
と混合することによつて更に優れた混合液晶を得
ることができる。
本発明に係る式（）の化合物は、式
The present invention provides 3.
The present invention relates to a novel nematic liquid crystal compound of a 4-difluorophenol derivative. The novel nematic liquid crystal compound provided by the present invention has the general formula: [In the formula, R represents a linear alkyl group having 1 to 9 carbon atoms, and the two cyclohexane rings are each in a trans (equatorial-equatorial) configuration. ] It is a compound represented by Typical liquid crystal display cells include M. Schadt and others [APPLIED PHYSICS
LETTERS 18 , 127-128 (1971)] or G.H. Heilmeier et al. [PROCEEDING OF THE IEEE 56 1162
-1171 (1968)]
Cell) or G.H. Heilmeyer (G.
H Heilmeier) etc. [APPLIED PHYSICS
LETTERS 13 91 (1968)] or D.
D L White et al. [JOURNAL OF APPLIED PHYSICS 45 ,
4718 (1974)]. The liquid crystal materials used in these liquid crystal display cells are required to have various properties, but having a nematic phase in a wide temperature range including room temperature is an important property that is commonly required for all types of display cells. .
Most of the materials that can be used for practical purposes with such properties are usually obtained by mixing several or more components, which consist of a compound that has a nematic phase near room temperature and a compound that has a nematic phase above room temperature. It is then prepared. Many of the above-mentioned mixed liquid crystals currently in practical use are required to have a nematic phase over the entire temperature range of at least -30°C to +65°C. In order to meet such requirements, 4,4'-substituted terphenyl, 4,4'-substituted biphenylcyclohexane, 4,4'-substituted biphenylcyclohexane,
4,4'-substituted benzoyloxybenzoic acid phenyl ester, which has a crystal phase-nematic phase transition temperature (C-N point) of about 100°C and a temperature of about 200°C.
The nematic phase-isotropic liquid phase transition temperature (N-I
Compounds having a point) are often used. However, these compounds have a negative effect on the N-
When mixed in an amount sufficient to bring the temperature of point I to 65°C or higher, it has the undesirable property of increasing the viscosity of the resulting mixed liquid crystal, thereby reducing the response speed. . Furthermore, one of the characteristics required of liquid crystal materials used in field effect cells, particularly TN cells, is low voltage operability. Generally, lowering the operating voltage of a liquid crystal display cell corresponds to lowering the threshold voltage Vth of the liquid crystal. When a compound having a high N-I point as mentioned above is mixed in a sufficient amount to make the N-I point of the mixed liquid crystal 65°C or higher, the threshold voltage of the resulting mixed liquid crystal will be increased. This has the undesirable property of increasing the operating voltage. The compound of formula () according to the present invention is a novel compound with improved properties. That is, the expression ()
By mixing the compound with one or more other nematic liquid crystal compounds, N
- When preparing a practical mixed liquid crystal having the I point, the viscosity and threshold voltage of the mixed liquid crystal are significantly increased, whereas the above-mentioned known liquid crystal compounds significantly increase the viscosity and/or threshold voltage. The increase in value voltage can be suppressed to a small extent. Furthermore, the compound of formula () is
It has extremely good compatibility with 4,4'-substituted cyclohexylcarboxylic acid phenyl ester, which was reported as a nematic liquid crystal material with excellent time-division driving characteristics in Publication No. 54-83694, so it cannot be mixed with these compounds. A more excellent mixed liquid crystal can be obtained by this method. The compound of formula () according to the present invention is a compound of formula ()
【式】で表わされる化合物
に、エーテル、ベンゼン、トルエンの如き不活性
有機溶媒中で、ピリジンの如き塩基性化合物を触
媒として３・４−ジフルオロフエノールを反応さ
せることにより製造できる。
斯くして製造された式（）の化合物の転移温
度を第１表に掲げる。It can be produced by reacting a compound represented by the formula with 3,4-difluorophenol in an inert organic solvent such as ether, benzene, or toluene using a basic compound such as pyridine as a catalyst. Table 1 lists the transition temperatures of the compounds of formula () thus produced.
【表】
本発明に係る式（）の化合物は弱い正の誘電
率異方性を有するネマチツク液晶化合物であり、
従つて例えば、負の誘電率異方性を有する他のネ
マチツク液晶化合物との混合物の状態で動的光散
乱型表示セルの材料として使用することができ、
また正又は負の誘電率異方性を有する他のネマチ
ツク液晶化合物との混合物の状態で電界効果型表
示セルの材料として使用することができる。
このように、式（）の化合物と混合して使用
することのできる好ましい代表例としては、例え
ば４・4′−置換安息香酸フエニルエステル、４・
4′−置換シクロヘキサンカルボン酸フエニルエス
テル、４・4′−置換シクロヘキサンカルボン酸ビ
フエニルエステル、４（４−置換シクロヘキサン
カルボニルオキシ）安息香酸4′−置換フエニルエ
ステル、４（４−置換シクロヘキシル）安息香酸
4′−置換フエニルエステル、４（４−置換シクロ
ヘキシル）安息香酸4′−置換シクロヘキシルエス
テル、４・4′−ビフエニル、４・4′−フエニルシ
クロヘキサン、４・4′−置換ターフエニル、４・
4′−ビフエニルシクロヘキサン、２（4′−置換フ
エニル）５−置換ピリミジンなどを挙げることが
できる。
第２表は時分割駆動特性の優れたネマチツク液
晶材料として現在汎用されている母体液晶(A)の80
重量％と第１表に示した式（）の化合物
No.1、No.2、No.3、No.4、No.5の各々の20重量
％とからなる各混合液晶について測定されたＮ−
Ｉ点と粘度としきい値電圧を掲示し、比較のため
に母体液晶(A)自体並びに、母体液晶(A)の80重量％
と式（）の化合物と構造が類似している公知の
化合物である式
の化合物の20重量％とから成る混合液晶について
測定されたＮ−Ｉ点と粘度としきい値電圧を掲示
したものである。
尚、母体液晶(A)は
20重量％の[Table] The compound of formula () according to the present invention is a nematic liquid crystal compound having weak positive dielectric constant anisotropy,
Therefore, for example, it can be used as a material for a dynamic light scattering type display cell in the state of a mixture with other nematic liquid crystal compounds having negative dielectric constant anisotropy.
It can also be used as a material for field-effect display cells in the form of a mixture with other nematic liquid crystal compounds having positive or negative dielectric anisotropy. Thus, preferred representative examples that can be used in combination with the compound of formula () include, for example, 4,4'-substituted benzoic acid phenyl ester, 4,4'-substituted benzoic acid phenyl ester,
4'-substituted cyclohexanecarboxylic acid phenyl ester, 4,4'-substituted cyclohexanecarboxylic acid biphenyl ester, 4(4-substituted cyclohexanecarbonyloxy)benzoic acid 4'-substituted phenyl ester, 4(4-substituted cyclohexyl) benzoic acid
4'-substituted phenyl ester, 4(4-substituted cyclohexyl)benzoic acid 4'-substituted cyclohexyl ester, 4,4'-biphenyl, 4,4'-phenylcyclohexane, 4,4'-substituted terphenyl, 4.
Examples include 4'-biphenylcyclohexane, 2(4'-substituted phenyl)5-substituted pyrimidine, and the like. Table 2 shows 80 base liquid crystals (A) that are currently widely used as nematic liquid crystal materials with excellent time-division drive characteristics.
Weight % and compound of formula () shown in Table 1
N− measured for each mixed liquid crystal consisting of 20% by weight of each of No.1, No.2, No.3, No.4, and No.5.
The I point, viscosity, and threshold voltage are posted, and for comparison, the base liquid crystal (A) itself and 80% by weight of the base liquid crystal (A)
is a known compound whose structure is similar to the compound of formula (). The NI point, viscosity, and threshold voltage measured for a mixed liquid crystal consisting of 20% by weight of the compound of In addition, the base liquid crystal (A) has a content of 20% by weight.
【式】 16重量％の【formula】 16% by weight
【式】 16重量％の【formula】 16% by weight
【式】 ８重量％の ８重量％の ８重量％の ８重量％の ８重量％の 及び ８重量％の から成るものである。[Formula] 8% by weight 8% by weight 8% by weight 8% by weight 8% by weight and 8% by weight It consists of
【表】
第２表に掲示したデータから、式（）の化合
物は、混合液晶の粘度及びしきい値電圧を大幅に
上昇せしめることなく、混合液晶のＮ−Ｉ点を実
用上充分なまでに上昇せしめ得ることが理解でき
るであろう。このように低い粘度で低いしきい値
電圧の混合液晶が得られるところに式（）の化
合物の実用上の高い価値がある。
本発明の効果は、下記の比較実験によつても明
らかにされる。化学構造が本発明に係る式（）
の化合物に類似しており、且つ混合液晶のＮ−Ｉ
点を高める目的で使用されている式
並びに式
の公知化合物夫々を前記の母体液晶(A)に種々の割
合で混合した。同様に本発明に係る化合物の１
つ、即ち式
の化合物を母体液晶(A)に種々の割合で混合した。
斯くして得られた３種類の混合液晶について、
夫々のＮ−Ｉ点と粘度としきい値電圧を測定し
た。これらの測定結果に基いて添付図面の第１図
にＮ−Ｉ点と粘度、第２図にＮ−Ｉ点としきい値
電圧の関係を示した。
これらの事実から、本発明に係る式（）の化
合物は代表的な公知の類似化合物に比べてＮ−Ｉ
点の上昇に伴う粘度及びしきい値電圧の上昇が遥
かに小さいことが理解できるであろう。
実施例 １
100c.c.のトルエンに13.0ｇ（0.100mol）の３・
４−ジフルオロフエノールと11.9ｇのピリジンを
溶解した溶液に式
[Table] From the data posted in Table 2, the compound of formula () can raise the N-I point of the mixed liquid crystal to a practically sufficient level without significantly increasing the viscosity and threshold voltage of the mixed liquid crystal. It will be understood that it can be increased. The practical value of the compound of formula () is that a mixed liquid crystal with low viscosity and low threshold voltage can be obtained. The effects of the present invention are also clarified by the following comparative experiments. Formula () whose chemical structure relates to the present invention
is similar to the compound of N-I of mixed liquid crystal.
Formulas used to increase points and expression Each of the known compounds was mixed in various proportions with the above-mentioned parent liquid crystal (A). Similarly, one of the compounds according to the present invention
one, i.e. The following compounds were mixed in various proportions into the base liquid crystal (A).
Regarding the three types of mixed liquid crystals obtained in this way,
The N-I point, viscosity, and threshold voltage of each were measured. Based on these measurement results, FIG. 1 of the attached drawings shows the relationship between the NI point and viscosity, and FIG. 2 shows the relationship between the NI point and the threshold voltage. Based on these facts, the compound of formula () according to the present invention has a higher N-I ratio than typical known similar compounds.
It can be seen that the increase in viscosity and threshold voltage with increasing point is much smaller. Example 1 13.0g (0.100mol) of 3.
In a solution of 4-difluorophenol and 11.9 g of pyridine, the formula
【式】の化合物の
29.9ｇ（0.100mol）を10℃で撹拌しながら滴下し
た。滴下終了後２時間還流温度で反応させ、反応
終了後、反応生成物をトルエンで抽出した。抽出
液を水洗、乾燥後、この液からトルエンを留去
し、得られた反応生成物をエタノールから再結晶
させて下記化合物30.2ｇ（0.0830mol）を得た。
収率 83.0％
転移温度 57℃（Ｃ→Ｎ）
153℃（ＮＩ）
実施例 ２
実施例１と同様の要領で下記化合物を得た。
収率 81.4％
転移温度 68℃（Ｃ→Ｎ）
133℃（ＮＩ）
実施例 ３
実施例１と同様の要領で下記化合物を得た。
収率 80.8％
転移温度 55℃（Ｃ→Ｎ）
145℃（ＮＩ）
実施例 ４
実施例１と同様の要領で下記化合物を得た。
収率 82.9％
転移温度 54℃（Ｃ→Ｎ）
156℃（ＮＩ）
実施例 ５
実施例１と同様の要領で下記化合物を得た。
収率 79.5％
転移温度 61℃（Ｃ→Ｎ）
140℃（ＮＩ）29.9 g (0.100 mol) of the compound of formula was added dropwise at 10° C. with stirring. After the completion of the dropwise addition, the reaction was carried out at reflux temperature for 2 hours, and after the completion of the reaction, the reaction product was extracted with toluene. After washing the extract with water and drying, toluene was distilled off from this liquid, and the obtained reaction product was recrystallized from ethanol to obtain 30.2 g (0.0830 mol) of the following compound. Yield: 83.0% Transition temperature: 57°C (C→N) 153°C (NI) Example 2 The following compound was obtained in the same manner as in Example 1. Yield 81.4% Transition temperature 68°C (C→N) 133°C (NI) Example 3 The following compound was obtained in the same manner as in Example 1. Yield 80.8% Transition temperature 55°C (C→N) 145°C (NI) Example 4 The following compound was obtained in the same manner as in Example 1. Yield 82.9% Transition temperature 54°C (C→N) 156°C (NI) Example 5 The following compound was obtained in the same manner as in Example 1. Yield 79.5% Transition temperature 61℃ (C→N) 140℃ (NI)
第１図と第２図は本発明に係る化合物の１つで
あるNo.2の化合物及びこれと類似構造をもつ公
知化合物(a)と(b)の夫々を現在汎用されている母体
液晶(A)に添加して得られる混合液晶のＮ−Ｉ点と
粘度の関係及びＮ−Ｉ点としきい値電圧の関係を
夫々示す図表である。
Figures 1 and 2 show Compound No. 2, which is one of the compounds according to the present invention, and known compounds (a) and (b) with similar structures to the currently widely used host liquid crystal ( 2 is a chart showing the relationship between the NI point and viscosity, and the relationship between the NI point and threshold voltage of a mixed liquid crystal obtained by adding A).
Claims (1)
基を表わし、２つのシクロヘキサン環の配置はそ
れぞれトランス（エカトリアル−エカトリアル）
配置である。〕 で表わされる化合物。[Claims] 1. General formula [In the formula, R represents a linear alkyl group having 1 to 9 carbon atoms, and the configuration of the two cyclohexane rings is trans (equatorial-equatorial).
It is the arrangement. ] A compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15252683A JPS6045549A (en) | 1983-08-23 | 1983-08-23 | Novel nematic liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15252683A JPS6045549A (en) | 1983-08-23 | 1983-08-23 | Novel nematic liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6045549A JPS6045549A (en) | 1985-03-12 |
| JPS6254783B2 true JPS6254783B2 (en) | 1987-11-17 |
Family
ID=15542358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15252683A Granted JPS6045549A (en) | 1983-08-23 | 1983-08-23 | Novel nematic liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6045549A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61282328A (en) * | 1985-06-10 | 1986-12-12 | Chisso Corp | Cyclohexane derivative |
| DE3807958B4 (en) * | 1988-03-10 | 2004-03-18 | Merck Patent Gmbh | Super twisted liquid crystal display element |
| US6506462B1 (en) * | 1995-08-01 | 2003-01-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystalline medium |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5813544A (en) * | 1981-07-15 | 1983-01-26 | Chisso Corp | Trans-4-substituted cyclohexanecarboxylic acid 3-chloro-4- fluorophenyl ester |
-
1983
- 1983-08-23 JP JP15252683A patent/JPS6045549A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5813544A (en) * | 1981-07-15 | 1983-01-26 | Chisso Corp | Trans-4-substituted cyclohexanecarboxylic acid 3-chloro-4- fluorophenyl ester |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6045549A (en) | 1985-03-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4673756A (en) | Nematic liquid crystalline compounds | |
| JPH0813764B2 (en) | New fluorine nematic liquid crystal compound | |
| EP0044646A1 (en) | 4-(Trans-4'-alkylcyclohexyl)benzoic acid 4"'-cyano-4"-biphenylyl esters and liquid crystal compositions containing them | |
| KR920009973B1 (en) | Process for preparing 4-substituted phenyl crotyl ether derivative | |
| JPS6254783B2 (en) | ||
| JPS6124382B2 (en) | ||
| JPH0247978B2 (en) | SHINKINEMACHITSUKUEKISHOKAGOBUTSU | |
| JPS6152141B2 (en) | ||
| JPH0256343B2 (en) | ||
| JPS63238041A (en) | Novel nematic liquid crystal compound | |
| JP2829436B2 (en) | Cyclobutane derivative | |
| JPH0158238B2 (en) | ||
| JP2932633B2 (en) | Fluorine compound having ether bond | |
| JP2949151B2 (en) | Tricyclic liquid crystalline compound having ether bonding | |
| JP2949866B2 (en) | Ether-based tricyclic liquid crystal compound, liquid crystal composition using the same, and liquid crystal display device | |
| JPH066705B2 (en) | Liquid crystal composition containing 4-substituted phenyl crotyl ether derivative | |
| JP2822529B2 (en) | Ether-based thinning liquid crystal | |
| JP2991454B2 (en) | Cyanophenylcyclohexyldioxane having an ether bond | |
| JP2881994B2 (en) | Cyclohexylcyclohexane derivative | |
| JPS62286943A (en) | 4'-substituted biphenyl crotyl ether derivative | |
| JPH0565236A (en) | Fluorotolan alkenyl compound | |
| JPS629590B2 (en) | ||
| JPS58203943A (en) | Novel nematic liquid crystal compound | |
| JPH0455B2 (en) | ||
| JPH0639452B2 (en) | New tolan ester |