JPS642094B2 - - Google Patents
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- Publication number
- JPS642094B2 JPS642094B2 JP2550281A JP2550281A JPS642094B2 JP S642094 B2 JPS642094 B2 JP S642094B2 JP 2550281 A JP2550281 A JP 2550281A JP 2550281 A JP2550281 A JP 2550281A JP S642094 B2 JPS642094 B2 JP S642094B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- sample
- colorless liquid
- substance
- 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.)
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- 239000004973 liquid crystal related substance Substances 0.000 claims description 47
- 239000000126 substance Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims 2
- 239000012071 phase Substances 0.000 description 18
- 230000007704 transition Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000000704 physical effect Effects 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007791 liquid phase Substances 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
- 239000012044 organic layer Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
〔発明の利用分野〕
本発明は無色液晶性物質と該無色液晶性物質を
含む液晶組成物と該液晶組成物を液晶層とする液
晶表示素子とに関する。
〔発明の背景〕
本明細書において無色液晶性物質とは、可視光
を吸収しない液晶性物質を意味する。また、液晶
性物質は、これ自体では室温にて液晶相を示さず
とも液晶組成物の配合成分として有用な物質を含
む。
室温はもとより低温度の環境でも反答特性の優
れた液晶表示素子を得るには液晶温度範囲を低温
度領域まで広げる必要がある。このことは液晶組
成物の低粘度化を実現すれば可能となる。
従来の代表的な液晶性物質
（ｍ，ｎは整数）は上記の目的の為には高粘度
である。一方、一般式として類似の化合物
は低粘度であるが液晶相を示さない。両者の違い
から本発明者は次の結論に至つた。前者の如く
[Field of Application of the Invention] The present invention relates to a colorless liquid crystal substance, a liquid crystal composition containing the colorless liquid crystal substance, and a liquid crystal display element having the liquid crystal composition as a liquid crystal layer. [Background of the Invention] As used herein, a colorless liquid crystal substance means a liquid crystal substance that does not absorb visible light. Further, the liquid crystalline substance includes a substance that does not exhibit a liquid crystal phase by itself at room temperature but is useful as a compounding component of a liquid crystal composition. In order to obtain a liquid crystal display element with excellent response characteristics not only at room temperature but also in low temperature environments, it is necessary to extend the liquid crystal temperature range to the low temperature region. This becomes possible if the viscosity of the liquid crystal composition is reduced. Typical conventional liquid crystalline substances (m, n are integers) has a high viscosity for the above purpose. On the other hand, compounds with similar general formula has low viscosity but does not exhibit a liquid crystal phase. Based on the difference between the two, the inventor came to the following conclusion. like the former
【式】に酸素原子が直接結合しているもので は[Formula] has an oxygen atom directly bonded to it. teeth
本発明の無色液晶性物質は、
一般式
R3−Ａ−Ｂ−CH2O−R4 （）
〔但し、R3は炭素数２〜５のアルキル基、R4
は炭素数１〜５のアルキル基、Ａが
The colorless liquid crystalline substance of the present invention has the general formula R 3 -A-B-CH 2 O-R 4 () [However, R 3 is an alkyl group having 2 to 5 carbon atoms, R 4
is an alkyl group having 1 to 5 carbon atoms, and A is
【式】 のときＢは【formula】 When B is
【式】または[expression] or
【式】で、ＡがIn [formula], A is
【式】のと きＢは【Formula】Noto Ki B is
以下、本発明の実施例によつてより具体的に説
明する。尚、相転移温度や融解温度の値はその化
合物の純度や測定方法によつて若干の変動を伴う
ものである。また、Ｃは結晶相を、Ｓはスメクチ
ツク相を、Ｎはネマチツク相を、そしてＩは等方
液体相をそれぞれ示し、例えば結晶相からネマチ
ツク相への転移はＣ−Ｎと記号化する。相転移温
度の単位は℃である。相転移温度の説明中で
（ ）内の数値は、加熱時には転移せず冷却時の
み相転移するモノトロビツクの相転移温度を示
す。
実施例１ 〈一般式
Hereinafter, the present invention will be explained in more detail with reference to Examples. Note that the values of phase transition temperature and melting temperature are subject to slight variations depending on the purity of the compound and the measuring method. Further, C represents a crystalline phase, S represents a smectic phase, N represents a nematic phase, and I represents an isotropic liquid phase. For example, a transition from a crystalline phase to a nematic phase is symbolized as CN. The unit of phase transition temperature is °C. In the explanation of the phase transition temperature, the numerical value in parentheses indicates the phase transition temperature of a monotrovik, which does not undergo a phase transition during heating but undergoes a phase transition only during cooling. Example 1 <General formula
【式】で表わされる 無色液晶性物質の製造方法と物性〉 フラスコにLi〔AlH4〕31.2ｇとManufacturing method and physical properties of colorless liquid crystal substance represented by [Formula] 31.2 g of Li [AlH 4 ] in a flask and
【式】200ml
を入れて懸濁させておく。これに
[Formula] Add 200ml and suspend. to this
【式】180ｇの[Formula] 180g
【式】１溶液を水冷下撹拌しながら滴下
し、滴下終了後室温で６時間更に撹拌を続ける。
次にこの反応液を希塩酸に投入して撹拌し、有機
層を分離して溶媒を留去すると、
[Formula] 1 solution was added dropwise with stirring under water cooling, and after the dropwise addition was completed, stirring was further continued at room temperature for 6 hours.
Next, this reaction solution was poured into dilute hydrochloric acid and stirred, the organic layer was separated and the solvent was distilled off.
【式】が得られた。
別のフラスコSOCl235.7ｇ、ピリジン
[Formula] was obtained. Another flask SOCl 2 35.7g, pyridine
【式】1.4ｇ、ベンゼン[Formula] 1.4g, benzene
【式】100
mlを入れ還流撹拌させる。これに
[Formula] Add 100 ml and stir under reflux. to this
【式】39ｇ加え、４
時間還流撹拌する。この反応液を水に投入し、
Add 39g of [Formula] and stir under reflux for 4 hours. Pour this reaction solution into water,
【式】抽出し、[Formula] Extract,
【式】を留去するとWhen [formula] is distilled off,
【式】が得られた。
更に別のフラスコにC3H7OH100mlを入れ、
Na0.4ｇを加え、還流温度まで移温させておく。
これに[Formula] was obtained. Add 100ml of C 3 H 7 OH to another flask,
Add 0.4 g of Na and bring the temperature to reflux temperature.
to this
【式】５ｇを
加え、３〜４時間還流する。この反応液を濃縮
後、水へ投入して（C2H5）2O抽出を行い、
（C2H5）2Oを留去すると無色液晶性物質Add 5 g of the formula and reflux for 3 to 4 hours. After concentrating this reaction solution, it was poured into water and extracted with (C 2 H 5 ) 2 O.
(C 2 H 5 ) 2 O is distilled off to form a colorless liquid crystalline substance.
【式】（試料17）
が得られた。
試料17の元素分析値（Ｃ；83.30％，Ｈ；11.42
％）はC21H34Oの計算値とよく一致した。加えて
試料17の赤外吸収スペクトルは第１図の通りで
1110cm-1にエーテル結合の吸収が現われる。両事
実と原料化合物との関係から試料17は上記式の液
晶性物質であることを確認した。
試料17及び試料17に準ずる製造法にて得た他の
試料について相転移温度を表１に示す。[Formula] (Sample 17) was obtained. Elemental analysis value of sample 17 (C; 83.30%, H; 11.42
%) was in good agreement with the calculated value for C21H34O . In addition, the infrared absorption spectrum of sample 17 is shown in Figure 1.
Absorption of ether bond appears at 1110cm -1 . From both facts and the relationship with the raw material compounds, it was confirmed that Sample 17 was a liquid crystalline substance of the above formula. Table 1 shows the phase transition temperatures of Sample 17 and other samples obtained by a manufacturing method similar to Sample 17.
【表】
実施例２ 〈一般式
[Table] Example 2 <General formula
【式】で表わされる 無色液晶性物質の製造方法と物性〉 フラスコにRepresented by [formula] Manufacturing method and physical properties of colorless liquid crystal material> in a flask
【式】
189ｇとC2H5OH600mlを入れ、氷冷撹拌してお
く、これにNa〔BH4〕17.1ｇを少量ずつ添加した
後、室温で２時間撹拌を続ける。その後酢酸10ml
を加え更に水２を加えてから（C2H5）2O抽出を
行い、（C2H5）2Oを留去すると
[Formula] Add 189 g and 600 ml of C 2 H 5 OH and stir while cooling on ice. Add 17.1 g of Na[BH 4 ] little by little to this, and continue stirring at room temperature for 2 hours. Then 10ml of acetic acid
Add 2 more water, perform (C 2 H 5 ) 2 O extraction, and distill (C 2 H 5 ) 2 O off.
【式】が得られた。 次に別のフラスコにSOCl235.7ｇ、[Formula] was obtained. Next, add 35.7 g of SOCl 2 to another flask.
【式】 1.4ｇ【formula】 1.4g
【式】100mlの溶液を作り、これに[Formula] Make 100ml of solution and add it to
【式】38ｇを滴下
して４時間加熱還流する。この反応後を水に投入
し、[Formula] 38g was added dropwise and heated under reflux for 4 hours. After this reaction, put it in water,
【式】抽出し、[Formula] Extract,
【式】を留去するとWhen [formula] is distilled off,
【式】が得られた。
更に別のフラスコを用意してC3H7OH100mlに
Na0.4ｇを溶解しておき、これに
[Formula] was obtained. Prepare another flask and add 100ml of C 3 H 7 OH.
Dissolve 0.4g of Na and add to this
【式】4.9ｇを加え、
４時間加熱撹拌する。この反応液を水に投入して
（C2H5）2O抽出し、（C5H5）2Oを留去すると無色液
晶性物質の
Add 4.9g of [Formula] and heat and stir for 4 hours. This reaction solution was poured into water and extracted with (C 2 H 5 ) 2 O. When (C 5 H 5 ) 2 O was distilled off, a colorless liquid crystal substance was obtained.
【式】（試料
30）が得られた。
試料30の元素分析値（Ｃ；84.83％，Ｈ；9.73
％）はC21H28Oの計算値（Ｃ；85.08％，Ｈ；9.52
％）とよく一致した。加えて試料30の赤外吸収ス
ペクトルは第２図に通りで、1100cm-1にエーテル
結合の吸収が現われた。両事実と原料化合物との
関連から試料30は上記式の液晶性物質であること
を確認した。
試料30及び試料30に準ずる製造方法にて得た他
の試料について相転移温度を表２に示す。[Formula] (Sample 30) was obtained. Elemental analysis value of sample 30 (C; 84.83%, H; 9.73
%) is the calculated value of C 21 H 28 O (C; 85.08%, H; 9.52
%) was in good agreement. In addition, the infrared absorption spectrum of sample 30 is as shown in Figure 2, and an ether bond absorption appeared at 1100 cm -1 . Based on both facts and the relationship with the raw material compound, it was confirmed that Sample 30 was a liquid crystalline substance of the above formula. Table 2 shows the phase transition temperatures of Sample 30 and other samples obtained by a manufacturing method similar to Sample 30.
【表】
実施例３ 〈一般式
で表わされる無色液晶性物質の製造方法と物
性〉
フラスコに
67ｇのC2H5OH500ml溶液を作り、これを氷冷撹
拌しながら更にNa〔BH4〕11.4ｇを少量ずつ添加
する。その後３時間撹拌を続け、酢酸30mlを加え
た後、水に投入して（C2H5）2O抽出を行うと
が得られた。
次に別のフラスコにて
30ｇをSOCl2150mlに混合し、６時間還流して後
氷水に投入する。次いで析出物を濾別して水洗す
れば
が得られた。
更に別のフラスコでC3H7OH30mlにNa0.4ｇを
溶解しておき、これに
30ｇのジメチルホルムアミド（（CH3）2NCHO）
150ml溶液を加え、５時間加熱撹拌する。その後
反応液を水中に投入し析出物を濾別すると無色液
晶性物質
（試料35）が得られた。
試料35の元素分析値（Ｃ；85.19％，Ｈ；10.23
％）はC27H38Oの計算値（Ｃ；85.66％，Ｈ；
10.12％）とよく一致した。加えて試料35の赤外
吸収スペクトルは第３図の通りで、1100cm-1にエ
ーテル結合の吸収が現われた。両事実と原料化合
物との関連から試料35は上記式の液晶性物質であ
ることを確認した。
試料35の相転移温度はＣ−Ｎ；152℃，Ｎ−
Ｉ；175℃であつた。また試料35に準じて製造し
た。
（試料36）の相転移温度はＣ−Ｎ；158℃，Ｎ−
ｌ；177℃であつた。
実施例４ 〈一般式
で表わされる無色液晶性物質の物性〉
を原料とし、試料35に準じた製造法で
（試料37）が得られた。
試料37の元素分析値（Ｃ；87.25％，Ｈ；8.43
％）はC25H28Oの計算値（Ｃ；87.16％，Ｈ；8.19
％）とよく一致した。加えて試料37の赤外吸収ス
ペクトルは第４図の通りで、1100cm-1にエーテル
結合の吸収が現われた。両事実と原料化合物との
関連から試料35は上記式の液晶性物質であること
を確認した。
試料37の相転移温度はＣ−Ｓ；233℃，Ｓ−
Ｎ；240℃，Ｎ−Ｉが245℃であつた。
実施例５ 〈上記各実施例にて製造した無色液晶
性物質を配合成分とする無色液晶組成物の特
性〉
表３の通りの組成である無色ネマチツク液晶組
成物に更に上記各実施例にて製造した各試料を添
加した。こうして再調整された無色液晶組成物の
粘度を上記試料無添加の（すなわち母体液晶のみ
の）粘度と比較して表４に示す。[Table] Example 3 <General formula Manufacturing method and physical properties of a colorless liquid crystal substance expressed by A solution of 67 g of C 2 H 5 OH in 500 ml is prepared, and 11.4 g of Na[BH 4 ] is added little by little while stirring while cooling on ice. After that, stirring was continued for 3 hours, 30 ml of acetic acid was added, and the mixture was poured into water for (C 2 H 5 ) 2 O extraction. was gotten. then in another flask 30 g was mixed with 150 ml of SOCl 2 , refluxed for 6 hours, and then poured into ice water. Then, the precipitate is filtered and washed with water. was gotten. Furthermore, in another flask, dissolve 0.4 g of Na in 30 ml of C 3 H 7 OH, and add it to this. 30g dimethylformamide ((CH 3 ) 2 NCHO)
Add 150ml of the solution and heat and stir for 5 hours. After that, the reaction solution was poured into water and the precipitate was filtered out, resulting in a colorless liquid crystal substance. (Sample 35) was obtained. Elemental analysis value of sample 35 (C; 85.19%, H; 10.23
%) is the calculated value of C 27 H 38 O (C; 85.66%, H;
10.12%). In addition, the infrared absorption spectrum of sample 35 is as shown in Figure 3, and absorption of ether bonds appeared at 1100 cm -1 . Based on both facts and the relationship with the raw material compound, it was confirmed that Sample 35 was a liquid crystalline substance of the above formula. The phase transition temperature of sample 35 is C-N; 152℃, N-
I: The temperature was 175°C. It was also produced according to Sample 35. The phase transition temperature of (sample 36) is C-N; 158℃, N-
l; It was 177°C. Example 4 <General formula Physical properties of a colorless liquid crystal substance expressed by using the raw material and manufacturing method similar to sample 35. (Sample 37) was obtained. Elemental analysis value of sample 37 (C; 87.25%, H; 8.43
%) is the calculated value of C 25 H 28 O (C; 87.16%, H; 8.19
%) was in good agreement. In addition, the infrared absorption spectrum of sample 37 is as shown in Figure 4, and absorption of ether bonds appeared at 1100 cm -1 . Based on both facts and the relationship with the raw material compound, it was confirmed that Sample 35 was a liquid crystalline substance of the above formula. The phase transition temperature of sample 37 is C-S; 233℃, S-
N: 240°C, N-I was 245°C. Example 5 <Characteristics of a colorless liquid crystal composition containing the colorless liquid crystal material produced in each of the above Examples as a compounding component> A colorless nematic liquid crystal composition having a composition as shown in Table 3 was further produced in each of the above Examples. each sample was added. The viscosity of the colorless liquid crystal composition thus readjusted is shown in Table 4 in comparison with the viscosity of the sample without addition (that is, only the base liquid crystal).
【表】【table】
【表】
表４から明らかなように、本発明による無色液
晶組成物は夫々対応する母体液晶に比べて粘度が
10〜30％低くなつた。
次に本発明による無色液晶組成物の液晶温度範
囲を比較例と共に表５に示す。尚、いずれも母体
液晶をＢとするデータである。液晶温度範囲の欄
の（ ）内の数値は液晶温度範囲の温度幅を示
す。[Table] As is clear from Table 4, the colorless liquid crystal composition according to the present invention has a viscosity lower than that of the corresponding base liquid crystal.
It was 10-30% lower. Next, the liquid crystal temperature range of the colorless liquid crystal composition according to the present invention is shown in Table 5 together with comparative examples. It should be noted that both data are based on B as the parent liquid crystal. The numbers in parentheses in the liquid crystal temperature range column indicate the temperature width of the liquid crystal temperature range.
【表】【table】
以上に説明したように、本発明の無色液晶性物
質によれば、室温はもとより低温の環境から高温
の環境に至るまでの巾の広い液晶温度範囲を持つ
無色液晶組成物を得ることが可能となる。加えて
この無色液晶組成物を用いた液晶表示素子に優れ
た応答特性を与えるという効果がある。
As explained above, according to the colorless liquid crystal material of the present invention, it is possible to obtain a colorless liquid crystal composition having a wide liquid crystal temperature range from room temperature to low temperature environments to high temperature environments. Become. In addition, it has the effect of imparting excellent response characteristics to a liquid crystal display element using this colorless liquid crystal composition.
第１図〜第４図は本発明による各種の無色液晶
性物質の赤外線吸収スペクトルである。
1 to 4 are infrared absorption spectra of various colorless liquid crystal materials according to the present invention.
Claims (1)
は炭素数１〜５のアルキル基、Ａが【式】 のときＢは【式】【式】または 【式】で、Ａが【式】のと きＢは【式】を示す〕で表される 無色液晶性物質。 ２ 一般式 R3−Ａ−Ｂ−CH2O−R4 （） 〔但し、R3は炭素数２〜５のアルキル基、R4
は炭素数１〜５のアルキル基、Ａが【式】 のときＢは【式】【式】または 【式】で、Ａが【式】のと きＢは【式】を示す〕で表される 無色液晶性物質を含むことを特徴とする無色液晶
組成物。 ３ ２枚の対向する電極基板間に液晶層を挟持
し、該電極基板間に電圧を印加して該液晶層を光
学的に変調させる液晶表示素子において、前記液
晶層が、一般式 R3−Ａ−Ｂ−CH2O−R4 （） 〔但し、R3は炭素数２〜５のアルキル基、R4
は炭素数１〜５のアルキル基、Ａが【式】 のときＢは【式】【式】または 【式】で、Ａが【式】のと きＢは【式】を示す〕で表される 無色液晶性物質を含む無色液晶組成物であること
を特徴とする液晶表示素子。[Claims] 1 General formula R 3 -A-B-CH 2 O-R 4 () [However, R 3 is an alkyl group having 2 to 5 carbon atoms, R 4
is an alkyl group having 1 to 5 carbon atoms, when A is [formula], B is [formula] [formula] or [formula], and when A is [formula], B is [formula]] Colorless liquid crystal substance. 2 General formula R 3 -A-B-CH 2 O-R 4 () [However, R 3 is an alkyl group having 2 to 5 carbon atoms, R 4
is an alkyl group having 1 to 5 carbon atoms, when A is [formula], B is [formula] [formula] or [formula], and when A is [formula], B is [formula]] A colorless liquid crystal composition comprising a colorless liquid crystal substance. 3 In a liquid crystal display element in which a liquid crystal layer is sandwiched between two opposing electrode substrates and a voltage is applied between the electrode substrates to optically modulate the liquid crystal layer, the liquid crystal layer has the general formula R 3 − A-B-CH 2 O-R 4 () [However, R 3 is an alkyl group having 2 to 5 carbon atoms, R 4
is an alkyl group having 1 to 5 carbon atoms, when A is [formula], B is [formula] [formula] or [formula], and when A is [formula], B is [formula]] A liquid crystal display element characterized by being a colorless liquid crystal composition containing a colorless liquid crystal substance.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2550281A JPS57140737A (en) | 1981-02-25 | 1981-02-25 | Colorless liquid crystal substance, colorless liquid crystal composition, and display element of liquid crystal |
| EP82101339A EP0058981B1 (en) | 1981-02-25 | 1982-02-22 | Colorless liquid crystalline compounds |
| DE8282101339T DE3268611D1 (en) | 1981-02-25 | 1982-02-22 | Colorless liquid crystalline compounds |
| US06/352,019 US4564694A (en) | 1981-02-25 | 1982-02-24 | Colorless liquid crystalline compounds |
| US06/761,885 US4694098A (en) | 1981-02-25 | 1985-08-02 | Colorless liquid crystalline compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2550281A JPS57140737A (en) | 1981-02-25 | 1981-02-25 | Colorless liquid crystal substance, colorless liquid crystal composition, and display element of liquid crystal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57140737A JPS57140737A (en) | 1982-08-31 |
| JPS642094B2 true JPS642094B2 (en) | 1989-01-13 |
Family
ID=12167835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2550281A Granted JPS57140737A (en) | 1981-02-25 | 1981-02-25 | Colorless liquid crystal substance, colorless liquid crystal composition, and display element of liquid crystal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57140737A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5859956A (en) * | 1981-10-07 | 1983-04-09 | Chisso Corp | Trans-4-alkyloxymethyl-1-(4'-cyanophenyl)cycylhexanes |
| JPS58134046A (en) * | 1982-02-03 | 1983-08-10 | Chisso Corp | Trns-4-alkyloxymethyl-1-(4'-alkylbiphenylyl-4-cycloexanes |
| JPS58219137A (en) * | 1982-06-12 | 1983-12-20 | Chisso Corp | 4-(trans-4-alkyloxymethylcyclohexyl)-4'-(trans-4- alkylcyclohexyl)biphenyls |
| JPS5936634A (en) * | 1982-08-23 | 1984-02-28 | Kanto Kagaku Kk | Liquid crystal compound |
| DE3321373A1 (en) * | 1983-06-14 | 1984-12-20 | Merck Patent Gmbh, 6100 Darmstadt | BICYCLOHEXYLE |
| DE102011108708A1 (en) | 2010-09-25 | 2012-03-29 | Merck Patent Gmbh | Liquid crystal displays and liquid crystal media with homeotropic alignment |
| EP2918658B1 (en) | 2014-03-10 | 2020-05-13 | Merck Patent GmbH | Liquid crystalline media with homeotropic alignment |
-
1981
- 1981-02-25 JP JP2550281A patent/JPS57140737A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57140737A (en) | 1982-08-31 |
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