JPS5935901B2 - 1-Cyclohexyl-2-(4'-halolophenyl)ethane derivative - Google Patents
1-Cyclohexyl-2-(4'-halolophenyl)ethane derivativeInfo
- Publication number
- JPS5935901B2 JPS5935901B2 JP14173081A JP14173081A JPS5935901B2 JP S5935901 B2 JPS5935901 B2 JP S5935901B2 JP 14173081 A JP14173081 A JP 14173081A JP 14173081 A JP14173081 A JP 14173081A JP S5935901 B2 JPS5935901 B2 JP S5935901B2
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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 cyclohexylphenylethane derivatives useful as electro-optic display materials.
本発明によつて提供されるネマチツク液晶は一般式（Ｉ
）
〔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Ｊ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“−
ハロロフエニル）エタンである。The nematic liquid crystal provided by the present invention has the general formula (I
) [In the formula, R is a linear alkyl group having 1 to 7 carbon atoms, and X is C
1-(trans(equatorial-equatorial)- represented by J representing t, F and Br halogen atoms, respectively
4'-n-alkylcyclohexyl)-2-(4"-
Halolophenyl) ethane.
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〔
ＡＰＰＬ１ＥＤＰＨＹ５１Ｃ５ＬＥＴＴＥＲ５１８１２
７〜１２８（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−ＨＨｅｌｌｍｅ
ｌｅｒ）等〔ＰＬ０ＣＥＥＤ１ＮＧ０ＦＴＨＥ１Ｅ、Ｅ
、Ｅ、５６１１６２〜１１７１（１９６８〕によつて提
案された動的光散型セル（ダイナミック・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。The compound of formula (I) is a compound having weak positive dielectric anisotropy, and for example, M-Schadt et al.
APPL1EDPHY51C5LETTER51812
7-128 (1971)] or the field effect mode cell proposed by G.H.
ler) etc. [PL0CEED1NG0FTHE1E,E
, E., 561162-1171 (1968) or the dynamic scattering mode cell proposed by G.H. Heilmeyer (G.
ＨＨｅｌｌｍｅｌｅｒ）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・ ７
、ススト型セルなどに適用することができる。式（Ｉ）
の化合物はネマチツクー等方性液体の転移温度が高＜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。HHellmeler) etc. [APPLIED PHYSI
CSLETTERS 13, 91 (1968)] or DL White etc. [JO
URNALOFAPPLIEDPHYSICS45, 4
718 (1974)] proposed by Guest 7
, it can be applied to instant type cells, etc. Formula (I)
This compound is characterized by a nematic isotropic liquid with a high transition temperature and low viscosity.It is also chemically very stable and decomposes when exposed to moisture, light, etc., and is colorless. It has many excellent properties, including a milky white color.
よつて式（１）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
がでぎる。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 ハロロビフエ
ニルに二硫化炭素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 ２，造する０第２段階 第１段階で
製造された式０Ｗ）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。Therefore, by using the compound of formula (1), 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. First step: Halolobiphenyl is reacted with a compound of formula () and anhydrous aluminum chloride in carbon disulfide or nitrobenzene to form a compound of formula (11).
2. Production of the compound of formula (1) 2. The compound of formula (W) produced in the first step is reacted with hydrazine and potassium hydroxide in diethylene glycol or triethylene glycol to produce the compound of formula (1). do.
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、Ｉは等方件液体を
夫々表わす。In the table, C represents a crystal, N represents a nematic phase, and I represents an 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）の以合物は、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 and other nematic liquid crystals. It can be used in the form of a mixture with a compound and/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 It is recommended to use a mixture of/or a non-nematic liquid crystal compound.
式山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、大きい正の誘電率異方件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Ｎ，型液晶同
族体という）、負又は小さい正の誘電律異方件をもつネ
マチツク液晶化合物（以下Ｎｎ早液晶という）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
自まれる。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 Shikiyama's compound include nematic liquid crystal compounds with large positive dielectric anisotropy (hereinafter referred to as Np-type liquid crystals) and/or or non-nematic liquid crystal compounds that are homologs of Np-type liquid crystals (hereinafter referred to as N-type liquid crystal homologues), nematic liquid crystal compounds having negative or small positive dielectric law anisotropy (hereinafter referred to as Nn fast liquid crystals), and/or Nn Non-nematic liquid crystal compounds (
(hereinafter referred to as Nn-type liquid crystal homologs), and mixtures thereof are also produced. 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＋１−，
ｎ−ＣｍＨ２ｍ＋，−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+1-, n-CmH2m+, -0- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，−，
ｎ−ＣｍＨ２ｍ＋，−０−のいずれかを表わす（但し、
ｍはｌ〜８の整数）。] [In the formula, R represents either n-CmH2m+, -, 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ｌ〜１０の整数）。] [In the formula, R represents n-CmH2m+1- (however,
m is an integer from 1 to 10).
〕 ４〔式中、Ｒはｎ−ＣｍＨ
２ｍ＋１− ９４−一 １１− −一 ７ー一
５４≦ −ー一Ｔｌのいずれかを表わす（但し、ｍは１
〜１０の整均〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，一を表
わす（但し、ｍ（ｔ］〜８の整数）。] 4 [wherein, R is n-CmH
2m+1-94-1 11--1 7-1 54≦--1Tl (however, m is 1
-10 [In the formula, R represents n-CmH2m+, 1 (provided that m(t] is an integer of -8).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，一，
ｎ−ＣｍＨ２ｍ＋１−０−のいずれかを表わす（但し、
ｍはｌ〜１０の整数）。] [In the formula, R represents either n-CmH2m+, 1, or n-CmH2m+1-0- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−，
ｎ−ＣｍＨ２ｍ＋１−０−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+1-0- (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）Ω〔式中、Ｒはｎ−ＣｍＨ２ｍ＋
，−を表わし、ＸはＦ，Ｃｔ，Ｂｒ，のいずれかを表わ
す（但し、ｍはｌ〜８の整数χ〕〔式中、Ｒはｎ−ＣＩ
ｌｌＨ２ｍ＋１−を表わす（但し、ｍは】〜】Ｏの整数
）。] [In the formula, R represents n-CmH2m+1- (however,
m is an integer from 1 to 10) Ω [wherein, R is n-CmH2m+
, -, and X represents any one of F, Ct, Br (however, m is an integer χ from 1 to 8)
llH2m+1- (where m is an integer from ] to ]O).
〕〔式中、Ｒ及びＲ′は夫々ｎ−ＣｍＨ２ｍ＋１−を表
わす（但し、ｍはｌ〜５の整数）。] [In the formula, R and R' each represent n-CmH2m+1- (wherein, m is an integer of 1 to 5).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１ し、ｍはＩ−１０の整数）。] [In the formula, R is n-CmH2m+1 and m is an integer of I-10).
〕を表わす（但
〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，一を表わす（但し、ｍ
は１〜１０の整数）。] (wherein, R represents n-CmH2m+, one (however, m
is an integer from 1 to 10).
〕〔式中、ｍまｎ−Ｃｎｌｌｌ２ｍ＋１ はｌ〜１０の整数）。] [In the formula, mmann-Cnllll2m+1 is an integer from 1 to 10).
〕を表わす（但し、
ｍ
〔式中、Ｒはｎ−ＣｍＨ２ｍ＋１−を表わす（但し、ｍ
は１〜１０の整数）。] (where m [wherein, R represents n-CmH2m+1- (however, m
is an integer from 1 to 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
列を列記する。] Next, specific examples of preferable 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＋， のいずれかを表わす（但し、 ｍは１〜１ ０の整耽）］ 〔式中、 Ｒ及びＲ′は夫々ｎ−ＣｍＨ２ｍ＋， いずれかを表わす（但し、 ｍはＩ〜１ ０の整数）。[During the ceremony, R and R' are respectively n-CmH2m+, (However, m is 1~1 0's calmness)] [During the ceremony, R and R' are respectively n-CmH2m+, Represents either (however, m is I~1 0 integer).
〕〔式中、Ｒ及びＲ′は夫々ｎ−ＣｍＨ２ｍ＋１−，ｎ
−Ｃｍ｝１２ｍ＋１−０−のいずれかを表わす（但し、
ｍは１〜１０の整数）。[In the formula, R and R' are respectively n-CmH2m+1-, n
-Cm}12m+1-0- (however,
m is an integer from 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋［を表わし、Ｒ′はｎ
−Ｃｍ′Ｈ２ｍ′＋，−，ｎ−Ｃｍ′Ｈ２ｍ′＋，−←
、ｎ−Ｃｍ′Ｈ２ｍ′＋１−ｃｍのいずれかを表わす（
但し、ｍ及びｍ′は夫々１〜１０の整数）。] [In the formula, R represents n-CmH2m+[, and R' is n
-Cm'H2m'+,-,n-Cm'H2m'+,-←
, n-Cm'H2m'+1-cm (
However, m and m' are each integers of 1 to 10).
〕〔式中、Ｒはｎ−ＣｍＨ２ｍ＋，−を表わし、Ｒ′は
ｎ−Ｃｍ′Ｈ２ｍ′＋１−，ｎ−Ｃｍ′Ｈ２ｍ′，−０
−のいずれかを表わすＣ但し、ｍ及びｍ′は夫々１〜１
０の整数）。〕〔式中、Ｒ及びＲ′は夫々ｎ−ｃｍＨ２
ｍ＋１−，ｎ−ｃｍＨ２ｍ＋１−０−のいずれかを表わ
す（但し、ｍはｌ〜６の整数）Ｑｌｌ〔式中、Ｒ及びＲ
′は夫々ｎ−ｃｍＨ２ｍ＋１ｎ−ｃｍＨ２ｍ＋１−０−
のいずれかを表わす（但し、ｍは１〜８の整数）。[In the formula, R represents n-CmH2m+,-, and R' represents n-Cm'H2m'+1-, n-Cm'H2m',-0
-C, where m and m' are each 1 to 1
0 integer). [In the formula, R and R' are each n-cmH2
Qll represents either m+1-, n-cmH2m+1-0- (where m is an integer of 1 to 6) [wherein R and R
' are respectively n-cmH2m+1n-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１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型態で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態でＦＥＭセル用
液晶として使用できる。In addition, it can be used as a liquid crystal for FEM cells 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 homologue. Can be used.
次に本発明を実施例をもつて具体的に説明する。Next, the present invention will be specifically explained using examples.
実施例 １二硫化炭素】００ａ中に無水塩化アルミニウ
ム１６．０９（０．１２０ｍｏｌ）を加え、室温で撹拌
しながらトランス−４−ｎ−プロピルシクロヘキシル酢
酸クロライド２０．３９（０．１００ｍｏｌ）を滴下し
た。Example 1 16.09 (0.120 mol) of anhydrous aluminum chloride was added to carbon disulfide 00a, and 20.39 (0.100 mol) of trans-4-n-propylcyclohexyl acetic acid chloride was added dropwise while stirring at room temperature. .
これを１０℃に冷却し、攪拌しながらｐ−フロロベンゼ
ン９．６９（０．１００ｍｏ１）を徐々に滴下し、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時間攪拌した。冷却後エーテルで抽出し
水洗、乾燥し、エーテル留去後、真空蒸留し下記化合物
１８．１９（０．０６９１ｍｏｌ）を得た。この化合物
にトリエチレングリコール１００ｍｌ１８０％ヒドラジ
ンハイドライド１２．１９（０．１９３ｍ０１）、８５
％水酸化カリウム２２．８９（０．３４６ｍｏｌ）を加
え、撹拌しながら温度を徐々に上げ１５０℃で３時間反
応させた。This was cooled to 10°C, and 9.69 (0.100 mo1) of p-fluorobenzene was gradually added dropwise while stirring.
After reacting at °C for 5 hours, the mixture was returned to room temperature and reacted for 2 hours. After the reaction, carbon disulfide was distilled off, and the mixture was added to ice water and stirred at 60°C for 1 hour. After cooling, the mixture was extracted with ether, washed with water, dried, and after distilling off the ether, vacuum distillation was performed to obtain the following compound 18.19 (0.0691 mol). To this compound, 100 ml of triethylene glycol, 180% hydrazine hydride 12.19 (0.193 m01), 85
% potassium hydroxide (0.346 mol) was added, the temperature was gradually raised while stirring, and the reaction was carried out at 150° C. for 3 hours.
冷却後、水１５０ｍｌをカロえ、ｎ−へ午サンで抽出し
た。水で洗浄後、無水硫酸ナトリウムで乾燥した後、ｎ
−へ午サンを留去し真空蒸留精製し、下記化合物】３．
２９（０．０５３２ｍｏｌ）を得た。実施例 ２
実施例１と同様の要領で下記化合物を得た。After cooling, 150 ml of water was poured into the mixture and extracted with n-hegosan. After washing with water and drying with anhydrous sodium sulfate,
- Distill the hedonium and purify it by vacuum distillation to produce the following compound] 3.
29 (0.0532 mol) was obtained. Example 2 The following compound was obtained in the same manner as in Example 1.
実施例 ３実施例１と同様の要領で下記化合物を得た。Example 3 The following compound was obtained in the same manner as in Example 1.
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 |
|---|---|---|---|
| JP14173081A JPS5935901B2 (en) | 1981-09-10 | 1981-09-10 | 1-Cyclohexyl-2-(4'-halolophenyl)ethane derivative |
| US06/413,798 US4455443A (en) | 1981-09-10 | 1982-09-01 | Nematic halogen Compound |
| DE19823233641 DE3233641C2 (en) | 1981-09-10 | 1982-09-10 | New nematic halogen compounds |
| CH539782A CH650238A5 (en) | 1981-09-10 | 1982-09-10 | 1-CYCLOHEXYL-2-PHENYLAETHANE AND -BIPHENYLAETHANE. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14173081A JPS5935901B2 (en) | 1981-09-10 | 1981-09-10 | 1-Cyclohexyl-2-(4'-halolophenyl)ethane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5849325A JPS5849325A (en) | 1983-03-23 |
| JPS5935901B2 true JPS5935901B2 (en) | 1984-08-31 |
Family
ID=15298868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14173081A Expired JPS5935901B2 (en) | 1981-09-10 | 1981-09-10 | 1-Cyclohexyl-2-(4'-halolophenyl)ethane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5935901B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE59108608D1 (en) * | 1990-04-13 | 1997-04-17 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM |
| EP0481032A1 (en) * | 1990-04-13 | 1992-04-22 | MERCK PATENT GmbH | Liquid crystalline medium |
| DE59108431D1 (en) * | 1990-04-13 | 1997-02-06 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM |
| DE4107119A1 (en) * | 1990-08-03 | 1992-02-06 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM |
-
1981
- 1981-09-10 JP JP14173081A patent/JPS5935901B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5849325A (en) | 1983-03-23 |
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