JPS6366839B2 - - Google Patents
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- Publication number
- JPS6366839B2 JPS6366839B2 JP60161003A JP16100385A JPS6366839B2 JP S6366839 B2 JPS6366839 B2 JP S6366839B2 JP 60161003 A JP60161003 A JP 60161003A JP 16100385 A JP16100385 A JP 16100385A JP S6366839 B2 JPS6366839 B2 JP S6366839B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- general formula
- nematic liquid
- carbon atoms
- 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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- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052801 chlorine Chemical group 0.000 claims description 12
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000004973 liquid crystal related substance Substances 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- KKMZQOIASVGJQE-UHFFFAOYSA-N 3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CS1 KKMZQOIASVGJQE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- DAKIDYQCFJQMDF-UHFFFAOYSA-N dichloromethane;pyridine Chemical compound ClCCl.C1=CC=NC=C1 DAKIDYQCFJQMDF-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- -1 hydroquinone ester Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 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
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
［発明の技術分野］
本発明は広い温度範囲で液晶相を示す新規なチ
オフエン系ネマチツク液晶化合物、この化合物を
含む液晶組成物および前記液晶化合物の製造方法
に関する。
［発明の技術的背景］
液晶は電場や磁場の影響を受けて配向をかえ
て、光散乱、複屈折等の光学的性質を顕著に変え
る性質があり、広く電気的表示装置に利用されて
いる。このような表示装置に用いられる液晶に要
求される性質は液晶温度範囲が広く、低粘性であ
ること、誘電異方性が高く、化学的に安定である
こと等が要求される。
［発明の目的］
本発明は高温状態での広い液晶温度範囲を有す
る新規なチオフエン系ネマチツク液晶化合物、こ
の化合物を含む液晶組成物および前記化合物の製
造方法を提供することを目的とする。
［発明の構成］
すなわち本発明のネマチツク液晶化合物は
一般式
（式中、Ｒは炭素原子数１〜10の直鎖アルキル
基、Ｘは水素原子、メチル基または塩素原子を示
す）で表されることを特徴とする。
本発明に含まれる化合物としては
一般式
一般式
（式中Ｒは炭素原子数１〜10の直鎖アルキル基を
示す）で表される１，４−ビス−（５−アルキル
−２−チエニルアクリル酸）ハイドロキノンエス
テル、
（式中Ｒは炭素原子１〜10の直鎖アルキル基を示
す）で表される１，４−ビス−（５−アルキル−
２−チエニルアクリル酸）−２−メチル−ハイド
ロキノンエステル、一般式
（式中Ｒは炭素原子数１〜10の直鎖アルキル基を
示す）で表される１，４−ビス−（５−ｎ−アル
キル−２−チエニルアクリル酸）−２−クロロ−
ハイドロキノンエステルがあげられる。
またこれらの製造方法は、
(1) 一般式
（式中Ｒは炭素原子数１〜10の直鎖アルキル基
を示す）で表される化合物と
一般式
（式中Ｘは水素原子、メチル基または塩素原子
を示す）で表される化合物とを脱水剤の存在下
で反応させて一般式
（式中ＲおよびＸは前記と同じ意味を示す）で
表される化合物を得る方法と、
あるいは
(2) 一般式
（式中Ｒは炭素原子数１〜10の直鎖アルキル基
を示す）で表される化合物を塩素化剤と反応さ
せて
一般式
（式中Ｒは前記と同じ意味を示す）で表される
酸塩化物とし、次いで
一般式
（式中Ｘは水素原子、メチル基または塩素原子
を示す）で表される化合物と反応させて
一般式
（式中ＲおよびＸは前記と同じ意味）で表され
る化合物とを得る方法とがある。
また、本発明の液晶組成物は、前記一般式
（）で表される化合物を１種以上含むことを特
徴とする。
次に本発明の製造方法について述べる。
製造方法(1)においては脱水剤としてＮ−ハイド
ロキシフタルイミド、Ｎ，N′−ジサクシニイミ
ジルカルボネイト、Ｎ，N′−ジシクロヘキシル
カルボジイミド等が挙げられるが、特にＮ，
N′−ジシクロヘキシルカルボジイミドを用いる
N.Pravdic′らの方法（J.Chem.Soc.，4633，
1964）が好ましい。またＮ，N′−ジシクロヘキ
シルカルボジイミドは化合物（）に対し等モル
量を用い、ピリジンの存在下でジクロロメタン、
ジクロロエタン、四塩化炭素等の溶媒中で脱水反
応させ、１段階で目的とする化合物を得ることが
できる。
また製造方法(2)において用いられる塩素化剤と
しては、塩化チオニル、三塩化リン、五塩化リン
等が挙げられるが特に反応後の処理の容易さから
塩化チオニルが好ましい。塩化チオニルを用いた
場合、式（）の５−ｎ−アルキル−２−チエニ
ルアクリル酸に対して過剰モル量を用いて還流さ
せ、反応後、塩化チオニルを減圧下で留去すれば
よい。式（）の５−ｎ−アルキル−２−チエニ
ルアクリル酸クロライドと式（）のハイドロキ
ノン誘導体との反応は、エチルエーテル、ベンゼ
ン、酢酸エチル等の不活性溶媒中で行うが、特
に、溶解性の面から酢酸エチルが好ましい。また
反応中に生ずる塩化水素を系外に除くために、ピ
リジン、トリエチルアミン等の塩基性物質を加え
ることが好ましい。反応後の生成物は有機溶媒抽
出、水洗、結晶化等の処理により目的とする化合
物を得ることができる。
本発明で原料として用いる５−ｎ−アルキル−
２−チエニルアクリル酸は、本発明者等が先に特
許出願した方法（特願昭59−267133号、特願昭59
−26713号、特願昭60−55433号）で製造すること
ができる。
（式中、Ｒは炭素原子数１〜10の直鎖アルキル
基、R1はＲよりも炭素原子数が１だけ少ない直
鎖アルキル基を示す。）
第１段階では、チオフエンにｎ−アルキルカル
ボン酸の酸塩化物または酸無水物を反応させて、
式(a)のｎ−アルキル−２−チエニルケトンが製造
される。
第２段階では、ｎ−アルキル−２−チエニルケ
トンをエチレングリコール系溶媒の存在下で抱水
ヒドラジンで還元することにより式(b)の２−ｎ−
アルキルチオフエンが製造される。
第３段階では、エチルエーテルを溶媒として２
−ｎ−アルキルチオフエンをフエニルリチウムと
反応させ、次いでＮ，Ｎ−ジメチルホルムアミド
と反応させるか、またはオキシ塩化リンを触媒と
して、２−ｎ−アルキルチオフエンと、Ｎ，Ｎ−
ジメチルホルムアミドと反応させて、式(c)の５−
ｎ−アルキル−２−チオフエンアルデヒドが製造
される。
第４段階では、ナトリウムの存在下で５−ｎ−
アルキル−２−チオフエンアルデヒドと酢酸メチ
ルを還流して得られる５−ｎ−アルキル−２−チ
エニルアクリル酸メチルをアルカリ加水分解する
か、または少量のピペリジンを含むピリジンを溶
媒として、５−ｎ−アルキル−２−チオフエンア
ルデヒドとマロン酸とを反応させて式（）の５
−ｎ−アルキル−２−チエニルアクリル酸が製造
される。
式（）の化合物に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および非ネマチ
ツク液晶化合物としては次のような化合物が例示
される。
［式中ＲおよびR′はそれぞれｎ−CnH2n+1−、ｎ
−CnH2n+1−Ｏ−、
[Technical Field of the Invention] The present invention relates to a novel thiophene-based nematic liquid crystal compound exhibiting a liquid crystal phase over a wide temperature range, a liquid crystal composition containing this compound, and a method for producing the liquid crystal compound. [Technical Background of the Invention] Liquid crystals have the property of changing their orientation under the influence of electric or magnetic fields, significantly changing optical properties such as light scattering and birefringence, and are widely used in electrical display devices. . Properties required of the liquid crystal used in such display devices include a wide liquid crystal temperature range, low viscosity, high dielectric anisotropy, and chemical stability. [Objects of the Invention] An object of the present invention is to provide a novel thiophene-based nematic liquid crystal compound having a wide liquid crystal temperature range at high temperatures, a liquid crystal composition containing this compound, and a method for producing the compound. [Structure of the invention] That is, the nematic liquid crystal compound of the present invention has the general formula (In the formula, R is a linear alkyl group having 1 to 10 carbon atoms, and X is a hydrogen atom, a methyl group, or a chlorine atom.) The compounds included in the present invention have the following general formula: 1,4-bis-(5-alkyl-2-thienyl acrylic acid) hydroquinone ester represented by (in the formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms), 1,4-bis-(5-alkyl-
2-Thienyl acrylic acid)-2-methyl-hydroquinone ester, general formula 1,4-bis-(5-n-alkyl-2-thienyl acrylic acid)-2-chloro- (wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms)
Examples include hydroquinone esters. In addition, these manufacturing methods are as follows: (1) General formula (In the formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms) and the general formula (In the formula, X represents a hydrogen atom, a methyl group, or a chlorine atom) in the presence of a dehydrating agent to react with the general formula (In the formula, R and X have the same meanings as above.) Or (2) General formula (In the formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms) is reacted with a chlorinating agent, and the general formula (in the formula, R has the same meaning as above), and then the general formula (In the formula, X represents a hydrogen atom, a methyl group, or a chlorine atom) by reacting with a compound represented by the general formula (wherein R and X have the same meanings as above). Further, the liquid crystal composition of the present invention is characterized in that it contains one or more kinds of compounds represented by the above general formula (). Next, the manufacturing method of the present invention will be described. In the production method (1), examples of the dehydrating agent include N-hydroxyphthalimide, N,N'-disuccinimidyl carbonate, N,N'-dicyclohexylcarbodiimide, etc., but in particular N,
Using N′-dicyclohexylcarbodiimide
The method of N. Pravdic′ et al. (J. Chem. Soc., 4633,
1964) is preferred. In addition, N,N'-dicyclohexylcarbodiimide was used in an equimolar amount to the compound (), and in the presence of pyridine dichloromethane,
The desired compound can be obtained in one step by dehydration reaction in a solvent such as dichloroethane or carbon tetrachloride. The chlorinating agent used in production method (2) includes thionyl chloride, phosphorus trichloride, phosphorus pentachloride, etc., but thionyl chloride is particularly preferred from the viewpoint of ease of treatment after the reaction. When thionyl chloride is used, it may be refluxed using an excess molar amount with respect to 5-n-alkyl-2-thienyl acrylic acid of formula (), and after the reaction, thionyl chloride may be distilled off under reduced pressure. The reaction between the 5-n-alkyl-2-thienyl acrylic acid chloride of formula () and the hydroquinone derivative of formula () is carried out in an inert solvent such as ethyl ether, benzene, or ethyl acetate. From this point of view, ethyl acetate is preferred. Further, in order to remove hydrogen chloride generated during the reaction from the system, it is preferable to add a basic substance such as pyridine or triethylamine. The product after the reaction can be subjected to treatments such as organic solvent extraction, water washing, and crystallization to obtain the desired compound. 5-n-alkyl- used as a raw material in the present invention
2-thienyl acrylic acid was produced by the method for which the present inventors previously applied for a patent (Japanese Patent Application No. 1983-267133,
-26713, Japanese Patent Application No. 60-55433). (In the formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms, and R 1 represents a straight-chain alkyl group having 1 fewer carbon atoms than R.) In the first step, thiophene is By reacting acid chlorides or acid anhydrides,
An n-alkyl-2-thienyl ketone of formula (a) is produced. In the second step, the 2-n-
Alkylthiophenes are produced. In the third step, 2
-N-alkylthiophene is reacted with phenyllithium and then with N,N-dimethylformamide, or with 2-n-alkylthiophene and N,N-
5- of formula (c) by reacting with dimethylformamide
n-Alkyl-2-thiophenaldehyde is produced. In the fourth step, 5-n-
Methyl 5-n-alkyl-2-thienyl acrylate obtained by refluxing alkyl-2-thiophene aldehyde and methyl acetate is hydrolyzed with an alkali, or 5-n- 5 of the formula () by reacting alkyl-2-thiophenaldehyde and malonic acid.
-n-alkyl-2-thienyl acrylic acid is produced. Examples of other nematic liquid crystal compounds and non-nematic liquid crystal compounds that can be used in combination with the compound of formula () include the following compounds. [In the formula, R and R' are n−C n H 2n+1 −, n
−C n H 2n+1 −O−,
【式】
−CN、−NO2のいずれかを表わす（但し、ｍは
１〜10の整数）］
［式中ＲおよびR′はそれぞれｎ−CnH2n+1−、ｎ
−CnH2n+1−Ｏ−、[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R and R' are n−C n H 2n+1 −, n
−C n H 2n+1 −O−,
【式】
−CN、−NO2のいずれかを表す（但し、ｍは１
〜10の整数）］
［式中ＲおよびR′はそれぞれｎ−CnH2n+1−、ｎ
−CnH2n+1−Ｏ−、[Formula] Represents either -CN or -NO 2 (where m is 1
~10 integer)] [In the formula, R and R' are n−C n H 2n+1 −, n
−C n H 2n+1 −O−,
【式】
−CN、−NO2のいずれかを表わす（但し、ｍは
１〜10の整数）］
［式中ＲおよびR′はそれぞれｎ−CnH2n+1−、ｎ
−CnH2n+1−Ｏ−、[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R and R' are n−C n H 2n+1 −, n
−C n H 2n+1 −O−,
【式】
−CN、−NO2のいずれかを表わす（但し、ｍは
１〜10の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、R′はｎ−
CnH2n+1−、ｎ−CnH2n+1−Ｏ−、
[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R represents n−C n H 2n+1 −, R′ represents n−
C n H 2n+1 −, n−C n H 2n+1 −O−,
【式】−CN、−NO2のいず
れかを表わす（但し、ｍは１〜10の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、R′はｎ−
CnH2n+1−、ｎ−CnH2n+1−Ｏ−、
[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R represents n−C n H 2n+1 −, R′ represents n−
C n H 2n+1 −, n−C n H 2n+1 −O−,
【式】−CN、−NO2のい
ずれかを表わす（但し、ｍは１〜10の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、R′はｎ−
CnH2n+1−、ｎ−CnH2n+1−Ｏ−、
[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R represents n−C n H 2n+1 −, R′ represents n−
C n H 2n+1 −, n−C n H 2n+1 −O−,
【式】【formula】
【式】【formula】
【式】−CN、−NO2のい
ずれかを表わす（但し、ｍは１〜10の整数）］
［式中ＲおよびR′はそれぞれｎ−CnH2n+1−、ｎ
−CnH2n+1−Ｏ−、[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R and R' are n−C n H 2n+1 −, n
−C n H 2n+1 −O−,
【式】【formula】
【式】【formula】
【式】−CN、−NO2のい
ずれかを表わす（但し、ｍは１〜10の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、R′はｎ−
CnH2n+1−、ｎ−CnH2n+1−Ｏ−、
[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R represents n−C n H 2n+1 −, R′ represents n−
C n H 2n+1 −, n−C n H 2n+1 −O−,
【式】【formula】
【式】−CN、−NO2のい
ずれかを表わす（但し、ｍは１〜10の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、R′はｎ−
CnH2n+1−、ｎ−CnH2n+1−Ｏ−、
[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R represents n−C n H 2n+1 −, R′ represents n−
C n H 2n+1 −, n−C n H 2n+1 −O−,
【式】【formula】
【式】【formula】
【式】−CN、−NO2のい
ずれかを表わす（但し、ｍは１〜10の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、ＸはＦ、
Cl、Brのいずれかを表わす（但し、ｍは１〜10
の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、ＸはＦ、
Cl、Brのいずれかを表わす（但し、ｍは１〜10
の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、ＸはＦ、
Cl、Brのいずれかを表わす（但し、ｍは１〜10
の整数）］
［式中Ｒはｎ−CnH2n+1−を表わし、ＸはＦ、
Cl、Brのいずれかを表わす（但し、ｍは１〜10
の整数）］
［式中ＲおよびR′はｎ−CnH2n+1−、ｎ−Cn
H2n+1−Ｏ−を表わし、Ｘは−CNまたは−Brを
表わす（但し、ｍは１〜10の整数）］
次に本発明の主な液晶化合物の物理的特性を第
１表に示す。[Formula] Represents either -CN or -NO 2 (where m is an integer from 1 to 10)] [In the formula, R represents n−C n H 2n+1 −, X is F,
Represents either Cl or Br (however, m is 1 to 10
integer)] [In the formula, R represents n−C n H 2n+1 −, X is F,
Represents either Cl or Br (however, m is 1 to 10
integer)] [In the formula, R represents n−C n H 2n+1 −, X is F,
Represents either Cl or Br (however, m is 1 to 10
integer)] [In the formula, R represents n−C n H 2n+1 −, X is F,
Represents either Cl or Br (however, m is 1 to 10
integer)] [In the formula, R and R′ are n−C n H 2n+1 −, n−C n
H2n+1 -O-, X represents -CN or -Br (where m is an integer from 1 to 10)] Next, the physical properties of the main liquid crystal compounds of the present invention are shown in Table 1. .
【表】【table】
Claims (1)
Ｘは水素原子、メチル基または塩素原子を示す）
で表されることを特徴とするネマチツク液晶化合
物。 ２ Ｘが、水素原子である特許請求の範囲第１項
記載のネマチツク液晶化合物。 ３ Ｘが、メチル基である特許請求の範囲第１項
記載のネマチツク液晶化合物。 ４ Ｘが、塩素原子である特許請求の範囲第１項
記載のネマチツク液晶化合物。 ５ 一般式 （式中Ｒは炭素原子数１〜10の直鎖アルキル基、
Ｘは水素原子、メチル基または塩素原子を示す）
で表される化合物を１種以上含むことを特徴とす
る液晶組成物。 ６ 一般式 （式中Ｒは炭素原子数１〜10の直鎖アルキル基を
示す）で表される化合物と 一般式 （式中Ｘは水素原子、メチル基または塩素原子を
示す）で表される化合物とを脱水剤の存在下で反
応させて一般式 （式中ＲおよびＸは前記と同じ意味を示す）で表
される化合物を得ることを特徴とするネマチツク
液晶化合物の製造方法。 ７ 一般式 （式中Ｒは炭素原子数１〜10の直鎖アルキル基を
示す）で表される化合物を塩素化剤と反応させて 一般式 （式中Ｒは前記と同じ意味を示す）で表される酸
塩化物とし、次いで 一般式 （式中Ｘは水素原子、メチル基または塩素原子を
示す）で表される化合物と反応させて 一般式 （式中ＲおよびＸは前記と同じ意味を示す）で表
される化合物を得ることを特徴とするネマチツク
液晶化合物の製造方法。[Claims] 1. General formula (In the formula, R is a straight chain alkyl group having 1 to 10 carbon atoms,
(X represents a hydrogen atom, methyl group or chlorine atom)
A nematic liquid crystal compound characterized by: 2. The nematic liquid crystal compound according to claim 1, wherein X is a hydrogen atom. 3. The nematic liquid crystal compound according to claim 1, wherein X is a methyl group. 4. The nematic liquid crystal compound according to claim 1, wherein X is a chlorine atom. 5 General formula (In the formula, R is a straight chain alkyl group having 1 to 10 carbon atoms,
(X represents a hydrogen atom, methyl group or chlorine atom)
A liquid crystal composition comprising one or more compounds represented by: 6 General formula (In the formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms) and the general formula (In the formula, X represents a hydrogen atom, a methyl group, or a chlorine atom) in the presence of a dehydrating agent to react with the general formula A method for producing a nematic liquid crystal compound, which comprises obtaining a compound represented by the formula (wherein R and X have the same meanings as above). 7 General formula (In the formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms) is reacted with a chlorinating agent, and the general formula (in the formula, R has the same meaning as above), and then the general formula (In the formula, X represents a hydrogen atom, a methyl group, or a chlorine atom) by reacting with a compound represented by the general formula A method for producing a nematic liquid crystal compound, which comprises obtaining a compound represented by the formula (wherein R and X have the same meanings as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60161003A JPS6222778A (en) | 1985-07-20 | 1985-07-20 | Nematic liquid crystal compound, liquid crystal composition and production of said compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60161003A JPS6222778A (en) | 1985-07-20 | 1985-07-20 | Nematic liquid crystal compound, liquid crystal composition and production of said compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6222778A JPS6222778A (en) | 1987-01-30 |
| JPS6366839B2 true JPS6366839B2 (en) | 1988-12-22 |
Family
ID=15726726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60161003A Granted JPS6222778A (en) | 1985-07-20 | 1985-07-20 | Nematic liquid crystal compound, liquid crystal composition and production of said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6222778A (en) |
-
1985
- 1985-07-20 JP JP60161003A patent/JPS6222778A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6222778A (en) | 1987-01-30 |
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