JPS5935900B2 - 1-Cyclohexyl-2-(4'-halolobiphenyl)ethane derivative - Google Patents
1-Cyclohexyl-2-(4'-halolobiphenyl)ethane derivativeInfo
- Publication number
- JPS5935900B2 JPS5935900B2 JP14172881A JP14172881A JPS5935900B2 JP S5935900 B2 JPS5935900 B2 JP S5935900B2 JP 14172881 A JP14172881 A JP 14172881A JP 14172881 A JP14172881 A JP 14172881A JP S5935900 B2 JPS5935900 B2 JP S5935900B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- cmh2m
- liquid crystal
- integer
- compound
- 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
Description
【発明の詳細な説明】
本発明は電気光学的表示材料として有用なシクロヘキシ
ルビフェニルエタン誘導体の新規ネマチツク液晶化合物
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel nematic liquid crystal compounds of cyclohexyl biphenylethane derivatives useful as electro-optic display materials.
本発明によつて提供される新規ネマチツク液晶は一般式
〔式中、Ｒは炭素数１〜７の直鎖状アルキル基、ＸはＣ
ｔ）Ｆ及びＢｒのハロゲン原子を夫々表わす。The novel nematic liquid crystal provided by the present invention has the general formula [wherein R is a linear alkyl group having 1 to 7 carbon atoms, and X is C
t) Represents halogen atoms of F and Br, respectively.
〕で表わされる１−（トランス（エカトリアルーエカト
リアル）−４’−ｎ−アルキルシクロヘキシル）−２−
（４″−ハロロビフエニル）エタンである。式（Ｉ）の
化合物は弱い正の誘電異方性をもつ化合物であり例えば
、エム・シヤツト（Ｍ−Ｓｃｈａｄｔ）等〔ＡＰＰＬＩ
ＥＤＰＨＹＳＩＣＳＬＥＴＴＥＲＳ止１２７〜１２８（
１９７１）〕によつて提案された電界効果型セル（フィ
ールド・エフェクト・モード・セル）又はジー ・エイ
チ・ハイルマイヤー（Ｇ−ＨＨｅｉｌｍｅｌｅｒ）等〔
ＰＲ０ＣＥＥＤ１ＮＧ０ＦＴＨＥ１、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−
ＨＨｅｌｌｍｅｉｅｒ）等〔ＡＰＰＬＩＥＤＰＨＹＳＩ
ＣＳＬＥＴＴＥＲＳ１３、９１（１９６８）〕あるいは
デイー ・エル・ホワイト（ＤＬＷｈｉｔｅ）等〔ＪＯ
ＵＲＮＡＬＯＦＡＰＰＬＩＥＤＰＨＹＳＩＣＳ４５、４
７１８（１９７４）〕によつて提案されたゲスト・ホス
ト型セルなどに適用することができる。] 1-(trans(equatorial-equatorial)-4'-n-alkylcyclohexyl)-2-
(4″-halolobiphenyl)ethane. The compound of formula (I) is a compound with weak positive dielectric anisotropy, and for example, M-Schadt et al. [APPLI
EDPHYSICSLETTERS stops 127-128 (
1971)] or the field effect mode cell proposed by G-H Heilmeler et al.
PR0CEED1NG0FTHE1, E, E, E, 56
1162-1171 (1968)] or the dynamic scattering mode cell proposed by G.H.
HHellmeier) etc. [APPLIED PHYSI
CSLETTERS 13, 91 (1968)] or DL White etc. [JO
URNALOFAPPLIEDPHYSICS45, 4
718 (1974)].
式中の化合物はネマチツクー等方性液体の転移温度が高
く粘度が低いことを特色とするものであり、更に化学的
に非常に安定であつて水分、光等によつて分解せす、然
も無色乳白色といつた幾多の優れた特性を有している。The compound in the formula is characterized by a high nematic isotropic liquid transition temperature and low viscosity, and is also chemically very stable and decomposed by moisture, light, etc. It has many excellent properties including being colorless and milky white.
よつて式（Ｉ）の化合物を用いれば長寿命でネマチツク
温度範囲の広い高速応答の液晶表示素子を制作すること
ができる。本発明によれば、式（１）の化合物は次の製
造方法に従つて製造される。第１段階−Ｐ−ハロロビフ
エニルに二硫化炭索あるいはニトロベンゼン中で式（）
の化合物と無水塩化アルミニウムを反応させて式（１１
）の化合物を製造する。Therefore, by using the compound of formula (I), it is possible to produce a liquid crystal display element with a long life, a wide nematic temperature range, and a high speed response. According to the present invention, the compound of formula (1) is produced according to the following production method. 1st step - P-halolobiphenyl in carbon disulfide or nitrobenzene with the formula ()
The compound of formula (11) is reacted with anhydrous aluminum chloride.
).
第２段階一第１段階で製造された式（［ｌ）の化合物に
ジエチレングリコールあるいはトリエチレングリコール
中でヒドラジンと水酸化カリウムを反応させて式（１）
の化合物を製造する。Second Step - The compound of formula ([l) produced in the first step is reacted with hydrazine and potassium hydroxide in diethylene glycol or triethylene glycol to form formula (1).
Manufacture the compound.
斯くして製造された式（１）の化合物の転移温度を第１
表に掲げる。The transition temperature of the compound of formula (1) thus produced is
Listed in the table.
表中、Ｃは結晶、Ｎはネマチツク相、は等方性液体を夫
々表わす。In the table, C represents a crystal, N represents a nematic phase, and isotropic liquid.
電卓、腕時計その他の機器の表示素子材料として用いる
場合、式｛１）の化合物は、該化合物の２種以上の混合
物の形態或は該化合物の１種又は２種以上と他のネマチ
ツク液晶化合物及び／又は非ネマチツク液晶化合物との
混合物の形態で用いることができるが、好ましくは、式
（１）の化合物の２種以上の混合物を母体液晶とし、こ
の母体液晶に他のネマチツク液晶化合物及び／又は非ネ
マチツク液晶化合物を混合した形態で用いることが推奨
される。When used as a display element material for calculators, wristwatches, and other devices, the compound of formula {1) may be used in the form of a mixture of two or more of the compounds, or in the form of one or more of the compounds, other nematic liquid crystal compounds, and It can be used in the form of a mixture with/or a non-nematic liquid crystal compound, but preferably, a mixture of two or more compounds of formula (1) is used as a matrix liquid crystal, and this matrix liquid crystal is combined with other nematic liquid crystal compounds and/or It is recommended to use a mixture of non-nematic liquid crystal compounds.
式（１）の化合物と混合して使用することのできる他の
ネマチツク液晶化合物及び／又は非ネマチツク液晶化合
物には、大きい正の誘電▼異方性をもつネマチツク液晶
化合物（以下Ｎｐ型液晶という）及び／又はＮｐ型液晶
の同族体である非ネマチツク液晶化合物（以下Ｎｐ型液
晶同族体という）、負又は小さい正の誘電宰異方件をも
つネマチツク液晶化合物（以下Ｎｎ型液晶という）及び
／又はＮｎ型液晶の同族体である非ネマチツク液晶化合
物（以下Ｎｎ型液晶同族体という）、更にそれらの混合
物が含まれる。式（１）の化合物と混合して使用するこ
とのできるＮｐ型液晶及びＮｐ型液晶同族体の好ましい
具体例を次に列記する。Other nematic liquid crystal compounds and/or non-nematic liquid crystal compounds that can be used in combination with the compound of formula (1) include nematic liquid crystal compounds with large positive dielectric anisotropy (hereinafter referred to as Np-type liquid crystals); and/or non-nematic liquid crystal compounds that are homologs of Np-type liquid crystals (hereinafter referred to as Np-type liquid crystal homologs), nematic liquid crystal compounds having negative or small positive dielectric anisotropy (hereinafter referred to as Nn-type liquid crystals), and/or Non-nematic liquid crystal compounds that are homologs of Nn-type liquid crystals (hereinafter referred to as Nn-type liquid crystal homologues) and mixtures thereof are also included. Preferred specific examples of Np-type liquid crystals and Np-type liquid crystal analogs that can be used in combination with the compound of formula (1) are listed below.
〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，−，
ｎ−ＣｍＨ２ｍ＋１−０−のいずれかを表わす（但し、
ｍは１〜１０の整数）。[In the formula, R represents either n-CmH2m+, -, n-CmH2m+1-0- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−，
ｎ−ＣｍＨ２ｍ＋，−０−のいずれかを表わす（但し、
ｍは１〜８の整数）。] [In the formula, R represents either n-CmH2m+1-, n-CmH2m+, -0- (However,
m is an integer from 1 to 8).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−を表わす（但し、
ｍは１〜１０の整数）。] [In the formula, R represents n-CmH2m+1- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，
八
Ｕ
ｎ−ＣｍＨ２ｍ＋１−０−ｎ−ＣｍＨ２ｍ＋，−ｃｍ０
−のいずれかを表わす（但し、ｍは１〜１０の整数）」
〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−を表わす（但し、ｍ
はＩ〜８の整数）。[In the formula, R is n-CmH2m+, 8U n-CmH2m+1-0-n-CmH2m+, -cm0
- (where m is an integer from 1 to 10)
[In the formula, R represents n-CmH2m+1- (however, m
is an integer from I to 8).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，−，
ｎ−ＣｍＨ２ｍ＋１−０−のいずれかを表わす（但し、
ｍは１〜１０の整数）。] [In the formula, R represents either n-CmH2m+, -, n-CmH2m+1-0- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−Ｃｍｌｌｌ２ｍ＋，−，ｎ−ＣｍＨ
２ｍ＋１−０−のいずれかを表わす（但し、ｍは１〜８
の整数）。[In the formula, R is n-Cmll2m+,-,n-CmH
Represents either 2m+1-0- (where m is 1 to 8
integer).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，−を表わす（但し、
ｍは１〜１０の整数）。] [In the formula, R represents n-CmH2m+,- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−を表わし、ＸはＦ
，Ｃｔ，Ｂｒ，Ｉのいずれかを表わす（但し、ｍはｌ〜
８の整数）。[In the formula, R represents n-CmH2m+1-, and X is F
, Ct, Br, I (where m is l~
8 integers).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−を表わす（但し、
ｍはｌ〜１０の整数）。] [In the formula, R represents n-CmH2m+1- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒ及びＲ′は夫々ｎ−ＣｍＨ２ｍ＋，一を表
わす（但し、ｍは１〜５の整数）。] [In the formula, R and R' each represent n-CmH2m+, 1 (where m is an integer of 1 to 5).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−を表わす（但し、
ｍはＩ〜】０の整数）。] [In the formula, R represents n-CmH2m+1- (however,
m is an integer from I to ]0).
〕〔式中、Ｒはｎ−ＣｎｌＨ２ｍ＋，−を表わす（但し
、ｍはｌ−１０の整数）。] [In the formula, R represents n-CnlH2m+,- (however, m is an integer of 1-10).
〕ノ
〔式中、Ｒはｎ−ＣｍｌＩ２ｍ＋１−を表わす（但Ｌｓ
ｍはｌ〜１０の整数）。[In the formula, R represents n-CmlI2m+1- (However, Ls
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，−を表わす（但し、
ｍはｌ−１０の整数）。] [In the formula, R represents n-CmH2m+,- (however,
m is an integer of 1-10).
〕次に、式（１）の化合物と混合して使用することので
きるＮｎ型液晶及びＮｎ型液晶同族体の好ましい具体例
を列記する。] Next, preferred specific examples of Nn-type liquid crystals and Nn-type liquid crystal analogs that can be used in combination with the compound of formula (1) are listed.
〔式中、
Ｒ及びＲ′は夫々ｎ−ＣｍＨ２ｍ＋１
―陣〜ｌ畢▲曇▲具≦晶晶畢Ｔｌ▼ｆ１番番ｊ〆▲▲具
▲▲乙番番嘉丁１Ｖｊ１のいずれかを表わす（但し、ｍ
は１〜１０の整数）」〔式中、Ｒ及びＲ′は夫々ｎ−Ｃ
ｍＨ２ｍ＋１
ｎ−ＣｍＨ２ｍ＋１−０−，ｎ−ＣｍＨ２ｍ＋，−ｃｍ
のいずれかを表わす（但し、ｍはｌ〜１０の整数）。[In the formula, R and R' each represent one of n-CmH2m+1 -jin〜l畢▲cloud▲tool≦crystalline畢Tl▼f1No. However, m
is an integer from 1 to 10)" [wherein R and R' are each n-C
mH2m+1 n-CmH2m+1-0-, n-CmH2m+, -cm
(However, m is an integer from 1 to 10).
〕〔式中、Ｒ及びＲ′は夫々ｎ−ＣｍＨ２ｍ＋！ｎ−Ｃ
ｌＴｌｌｌ２ｍ＋１−０−のいずれかを表わす（但し、
ｍはｌ−１０の整数）。〕〔式中、Ｒはｎ−ＣｍＨ２ｍ
＋［を表わし、Ｒ′はｎ−Ｃｍ′Ｈ２ｍ′＋１−，ｎ−
Ｃｍ′Ｈ２ｍ′ゃ「０−，。[In the formula, R and R' are each n-CmH2m+! n-C
lTllll2m+1-0- (however,
m is an integer of 1-10). ] [In the formula, R is n-CmH2m
+ [represents R' is n-Cm'H2m'+1-, n-
Cm'H2m' ``0-,.
−Ｃｍ′Ｈ２ｍ５＋Ｉ−Ｃ−のいずれかを表わす（但し
ｍ及びｍ′は夫々１〜１０の整数）。〕〔式中、Ｒは
ｎ−ＣｍＨ２ｍ＋．，一を表わし、Ｒ７はｎ−Ｃｍ′Ｈ
２ｍ′１−， ｎ−Ｃｍ′Ｈ２ｍ′＋１−０−のいずれ
かを表わす（但し、ｍ及びｍ′は夫々ｌ〜１０の整数）
。〕〔式中、Ｒ及びＲ′は夫々ｎ−ＣｍＨ２ｍ＋］一，
ｎ−ＣｍＨ２ｍ＋１−０−のいずれかを表わす（但し、
ｍはｌ〜６の整数）。-Cm'H2m5+I-C- (where m and m' are each integers from 1 to 10). ] [In the formula, R is n-CmH2m+. , one, and R7 is n-Cm'H
2m'1-, n-Cm'H2m'+1-0- (however, m and m' are each integers from 1 to 10)
. ] [In the formula, R and R' are each n-CmH2m+]1,
n-CmH2m+1-0- (however,
m is an integer from 1 to 6).
〕〔式中、Ｒ及びＲ′は夫々ｎ−ｃｍＨ２ｍ＋１−，ｎ
−ｃｍＨ２ｍ＋１−０−のいずれかを表わす（但し、ｍ
はｌ〜８の整数）。[In the formula, R and R' are n-cmH2m+1-, n
-cmH2m+1-0- (however, m
is an integer from 1 to 8).
〕式（１）の化合物の２種以上の混合物の形態或は式（
１）の化合物のｌ種又は２種以上と前記したＮｎ型液晶
及び／又はその同族体との混合物の形態でＤＳＭセル用
液晶として使用できる。] In the form of a mixture of two or more compounds of formula (1) or in the form of a mixture of two or more compounds of formula (1)
It can be used as a liquid crystal for a DSM cell in the form of a mixture of one or more of the compounds 1) and the above-mentioned Nn-type liquid crystal and/or its homolog.
また、式（１）の化合物の１種又は２種以上と前記した
Ｎｐ型液晶及び／又はその同族体と前記したＮｎ型液晶
及び／又はその同族体との混合物の形※この化合物にト
リエチレングリコール２００ｍｅ８０％ヒドラジンハイ
ドライド１１．６９（０．１８５ｍ０１）、８５％水酸
化カリウム２１．７９（０．３３０ｍｏｌ）を加え、撹
拌しながら温度を徐々に上げ、１６０℃で３時間反応さ
せた。In addition, in the form of a mixture of one or more compounds of formula (1), the above-mentioned Np-type liquid crystal and/or its homologue, and the above-mentioned Nn-type liquid crystal and/or its homolog *This compound may contain triethylene Glycol 200me, 11.69 (0.185 m01) of 80% hydrazine hydride, and 21.79 (0.330 mol) of 85% potassium hydroxide were added, and the temperature was gradually raised while stirring, and the mixture was reacted at 160° C. for 3 hours.
冷却後、水３００態でＦＥＭセル用液晶として使用でき
る。次に本発明を実施例をもつて具体的に説明する。After cooling, it can be used as a liquid crystal for FEM cells in a water-300 state. Next, the present invention will be specifically explained using examples.
実施例 １二硫化炭素１００ｍｌ中に無水塩化アルミニ
ウム１６．０９（０．１２０ｍｏｌ）をカロえ室温で撹
拌しながらトランス−４−ｎ−プロピルシクロヘ午シル
酢酸クロライド２０．３９（０．１００ｍｏ１）を滴下
した。Example 1 16.09 (0.120 mol) of anhydrous aluminum chloride was added to 100 ml of carbon disulfide, and 20.39 (0.100 mol) of trans-4-n-propylcyclohexyl acetate chloride was added while stirring at room temperature. dripped.
これを１０℃に冷却し、撹拌しながらＰ−クロロビフエ
ニル１８．９９（０．１００ｍｏｌ）を二硫化炭素３０
ｒｆＬｌに溶解した溶液を滴下し、１０℃で５時間反応
させた後、室温にもどして２時間反応させた。反応後、
二硫化炭素を留去した後、これを氷水中に加え６０℃で
１時間撹拌した。冷却後、エーテルで抽出し、水洗、乾
燥しエーテル留去後エタノ一ルで再結晶精製し、下記化
合物２３．４９（０．０６６０ｍｏ１）を得た。＊ａを
加えべンゼンで抽出した。水で洗浄後、無水硫酸ナトリ
ウムで乾燥した後、べンゼンを留去し、ｎ−へ午サンー
エタノ一ルで再結晶精製し、下記化合物１６．６９（０
．０４８８ｍｏ１）を得た。実施例 ２二硫化炭素１０
０ａ中に無水塩化アルミニウム１６．０９（０．１２０
ｍｏｌ）をカロえ室温で撹拌しながらトランス−４−ｎ
−フ０ロピルシクロヘ午シル酢酸クロライド２０．３９
（０．１００ｍｏ１）を滴下した。This was cooled to 10°C, and while stirring, 18.99 (0.100 mol) of P-chlorobiphenyl was added to 30 mol of carbon disulfide.
A solution dissolved in rfLl was added dropwise and reacted at 10° C. for 5 hours, then returned to room temperature and reacted for 2 hours. After the reaction,
After carbon disulfide was distilled off, the mixture was added to ice water and stirred at 60°C for 1 hour. After cooling, it was extracted with ether, washed with water, dried, and after distilling off the ether, it was purified by recrystallization with ethanol to obtain the following compound 23.49 (0.0660 mol). *a was added and extracted with benzene. After washing with water and drying over anhydrous sodium sulfate, the benzene was distilled off and recrystallization was carried out with n-ethanol ethanol to obtain the following compound 16.69 (0
．． 0488mol) was obtained. Example 2 Carbon disulfide 10
Anhydrous aluminum chloride 16.09 (0.120
mol) and trans-4-n while stirring at room temperature.
-Furopylcyclohexylacetic acid chloride 20.39
(0.100mol) was added dropwise.
Claims (1)
ロゲン原子を夫々表わす。 〕で表わされる化合物。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R represents a linear alkyl group having 1 to 7 carbon atoms, and X represents a halogen atom. ] A compound represented by
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14172881A JPS5935900B2 (en) | 1981-09-10 | 1981-09-10 | 1-Cyclohexyl-2-(4'-halolobiphenyl)ethane derivative |
| US06/413,798 US4455443A (en) | 1981-09-10 | 1982-09-01 | Nematic halogen Compound |
| CH539782A CH650238A5 (en) | 1981-09-10 | 1982-09-10 | 1-CYCLOHEXYL-2-PHENYLAETHANE AND -BIPHENYLAETHANE. |
| DE19823233641 DE3233641C2 (en) | 1981-09-10 | 1982-09-10 | New nematic halogen compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14172881A JPS5935900B2 (en) | 1981-09-10 | 1981-09-10 | 1-Cyclohexyl-2-(4'-halolobiphenyl)ethane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5849324A JPS5849324A (en) | 1983-03-23 |
| JPS5935900B2 true JPS5935900B2 (en) | 1984-08-31 |
Family
ID=15298821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14172881A Expired JPS5935900B2 (en) | 1981-09-10 | 1981-09-10 | 1-Cyclohexyl-2-(4'-halolobiphenyl)ethane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5935900B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3321373A1 (en) * | 1983-06-14 | 1984-12-20 | Merck Patent Gmbh, 6100 Darmstadt | BICYCLOHEXYLE |
| EP0481032A1 (en) * | 1990-04-13 | 1992-04-22 | MERCK PATENT GmbH | Liquid crystalline medium |
| KR0171590B1 (en) * | 1990-04-13 | 1999-03-20 | 위르겐 호이만, 라인하르트 슈틀러 | Liquid crystalline medium |
| JP3293080B2 (en) * | 1990-04-13 | 2002-06-17 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Liquid crystal medium |
| JP3544207B2 (en) * | 1990-04-13 | 2004-07-21 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Liquid crystal medium |
| DE4107119A1 (en) * | 1990-08-03 | 1992-02-06 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM |
-
1981
- 1981-09-10 JP JP14172881A patent/JPS5935900B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5849324A (en) | 1983-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4814523A (en) | Nematic liquid crystal compound of four ring systems | |
| JPS588022A (en) | 1-cyclohexyl-2-cyclohexylbiphenylethane derivative | |
| JPS5935900B2 (en) | 1-Cyclohexyl-2-(4'-halolobiphenyl)ethane derivative | |
| JPS588023A (en) | 1,2-di-(cyclohexylphenyl)ethane derivative | |
| JPS5935901B2 (en) | 1-Cyclohexyl-2-(4'-halolophenyl)ethane derivative | |
| JPS6033411B2 (en) | 1-cyclohexyl-2-cyclohexyl phenylethane derivative | |
| EP0198714B1 (en) | Liquid cristalline compositions containing cyclohexylcyclohexene derivatives, and their use | |
| JPS5933566B2 (en) | 1,4-di-(cyclohexylethyl)biphenyl derivative | |
| JPS6388165A (en) | Liquid crystal | |
| JPH0247971B2 (en) | ||
| JPS59110630A (en) | 1-cyclohexyl-2-cyclohexylbiphenylethane derivative | |
| JPS6124382B2 (en) | ||
| JPS59110631A (en) | 1,4-di-(cyclohexylethyl) biphenyl derivative | |
| JPH0338572A (en) | Pyrimidine derivative | |
| JPS62286943A (en) | 4'-substituted biphenyl crotyl ether derivative | |
| JPS61158937A (en) | Novel liquid crystal compound for high temperature use | |
| JP2534547B2 (en) | Liquid crystal compound and liquid crystal composition containing the same | |
| JPS6287556A (en) | Ester compound | |
| JPS6039252B2 (en) | New cyclohexane liquid crystal compound | |
| JPH0567144B2 (en) | ||
| JPS61225147A (en) | Halogenoaromatic compound | |
| JPS61291536A (en) | Crotyloxybenzene derivative | |
| JPS6048945A (en) | Fluorinated cyclohexylbiphenyl | |
| JPH03279340A (en) | Ether-based tricyclic liquid crystal compound | |
| JPS628423B2 (en) |