JPH01193237A - Liquid crystal compound having alkyl group in side chain - Google Patents
Liquid crystal compound having alkyl group in side chainInfo
- Publication number
- JPH01193237A JPH01193237A JP1673788A JP1673788A JPH01193237A JP H01193237 A JPH01193237 A JP H01193237A JP 1673788 A JP1673788 A JP 1673788A JP 1673788 A JP1673788 A JP 1673788A JP H01193237 A JPH01193237 A JP H01193237A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- trans
- allyl
- formula
- alkyl group
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 7
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 28
- 150000001875 compounds Chemical class 0.000 title abstract description 19
- 239000000126 substance Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 18
- 238000005821 Claisen rearrangement reaction Methods 0.000 abstract description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical class C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000004990 Smectic liquid crystal Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- GZMMUVKMQPSLLS-YSXIEMCBSA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC=CC=2)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC=CC=2)CC1 GZMMUVKMQPSLLS-YSXIEMCBSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- -1 ester-based Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QRAZRBGYBYIGRL-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)phenol Chemical compound C1CC(CCCCC)CCC1C1=CC=C(O)C=C1 QRAZRBGYBYIGRL-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzonitrile Chemical compound C1CC(CCC)CCC1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- XNERPGOFCKZDHL-UHFFFAOYSA-N 4-cyclohexyl-2-propylphenol Chemical class C1=C(O)C(CCC)=CC(C2CCCCC2)=C1 XNERPGOFCKZDHL-UHFFFAOYSA-N 0.000 description 1
- FFIXAFACUXWNCV-VVPTUSLJSA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC(O)=CC=2)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC(O)=CC=2)CC1 FFIXAFACUXWNCV-VVPTUSLJSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、新規なアルコキシ１０ピルベンゼン類および
該化合物を有効成分とする液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to novel alkoxy-10-pyrubenzenes and liquid crystal compositions containing the compounds as active ingredients.
（従来の技術）
液晶を利用した表示素子は時計、電卓等に広く使用され
ている。これらの液晶表示素子は液晶物質の光学異方性
および誘電異方性を利用したものである。液晶相にはネ
マチック液晶相、スメクチック液晶相、コレステリック
液晶相があり、そのうちネマチック液晶を利用したもの
が最も広く実用化され、スメクチック液晶の応用開発が
さかんに行なわれている。(Prior Art) Display elements using liquid crystals are widely used in watches, calculators, and the like. These liquid crystal display elements utilize optical anisotropy and dielectric anisotropy of liquid crystal substances. There are three types of liquid crystal phases: nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase. Among these, those using nematic liquid crystal are most widely put into practical use, and applications of smectic liquid crystal are being actively developed.
それらには液晶表示に応用されている電気光学効果に対
応して、ＴＮ（ねじれネマチック）型、ＤＳ（動的散乱
）型、ゲスト・ホスト型、ＤＡＰ型等の表示素子があり
、それぞれ、に使用される液晶物質は自然界のなるべく
広い温度範囲で液晶相を示すものが望ましい。There are display elements such as TN (twisted nematic) type, DS (dynamic scattering) type, guest-host type, and DAP type, which correspond to the electro-optic effect applied to liquid crystal displays. It is desirable that the liquid crystal material used exhibits a liquid crystal phase over as wide a natural temperature range as possible.
現在のところ単一の液晶物質でそのような条件をみたす
物質はなく、数種の液晶物質またはさらに非液晶物質を
混合して実用に供している。これらの物質は水分、光、
熱、空気等に対しても安定であることを要求されている
。At present, there is no single liquid crystal substance that satisfies these conditions, and several types of liquid crystal substances or even non-liquid crystal substances are mixed and put into practical use. These substances include water, light,
It is also required to be stable against heat, air, etc.
近年表示素子の大型化が望まれ、スメクチック液晶を用
いたレーザー光書き込み型大画面デスプレイをＦ、Ｊ、
カーノ（Ｆ、コ、Ｋａｈｎ、Ａｐｐｌ Ｐｈｙｓ、Ｌｅ
ｔｔ、。In recent years, there has been a desire to increase the size of display elements, and large-screen displays using laser light writing using smectic liquid crystals have been developed.
Kahn (F, Ko, Kahn, Appl Phys, Le
tt.
２２、 １１１−１１３ （１９７３））が提案した。22, 111-113 (1973)).
これに用いられる液晶化合物は、スメクチック相 ネマ
チック相 等方性液体のような順で相転移しなければな
らない。The liquid crystal compound used for this purpose must undergo phase transitions in the order of smectic phase, nematic phase, and isotropic liquid.
又一方では従来のＴＮ型方式では表示品位が劣るため、
新たに一連のＳＴＮ （スーパーツイスト）型表示素子
が間、シャット、Ｆ６リーンフーツ（Ａｐｐｌ。On the other hand, the display quality of the conventional TN type method is inferior, so
A new series of STN (Super Twist) type display elements has been introduced between F6 Leanfoots (Appl.
Ｐｈｙｓ Ｌｅｔｔ、 ５０．２３６ （１９８７））
により開発され、大型化しても表示品位が劣らないので
すむものであ る。Phys Lett, 50.236 (1987))
It was developed by the company, and the display quality remains unchanged even when the display size is increased.
この方式に望まれる液晶の性買はに３／Ｋｌが大きく、
Ｋ２／Ｋｌ は小さい、 Δε／ε上は小さい値が望ま
れている （Ｍ、 ５ｃｈａｄｔ、 Ｆ、 Ｌｅｅｎｈ
ｏｕｔｓＳｏｃｉｅｔｙ ｆｏｒ ｉｎｆｏｒｍａｔｉ
ｏｎ ＤｉｓｐｌａｙＩｎｔｅｒｎａｔｉｏｎａｌ Ｓ
ｙｍｐｏｓｉｕ＠Ｄｉｇｅｓｔ ｏｆ Ｔｅｃｈｎｉｃ
ａｌＰａｐａｒｓ ｖｏｌ、 １０８ Ｎｅｗ ０ｒ
ｌｅａｎｓ、 Ｌｏｕｉｓｉａｎａ Ｍａｙ１２−１４
． ＜１９８７） ３７２−３７５）。The desired liquid crystal value for this method is 3/Kl, which is large.
K2/Kl is small, and Δε/ε is desired to have a small value (M, 5chadt, F, Leenh
outsSociety for information
on Display International S
ymposiu@Digest of Technic
alPapars vol, 108 New 0r
leans, Louisiana May 12-14
．． <1987) 372-375).
本発明の目的はＫ ３ ／ Ｋ Ｉが比較的大きく、又
、Δｎが小さく相溶性に優れており、上述のＳＴＮ型表
示素子に使用できる化合物であって液晶組成物として有
用な新規化合物を提供することである。An object of the present invention is to provide a novel compound which has a relatively large K 3 /K I and a small Δn and has excellent compatibility, which can be used in the above-mentioned STN display element and which is useful as a liquid crystal composition. It is to be.
他の目的は、該化合物を含有することを特徴とする液晶
組成物を提供することである。Another object is to provide a liquid crystal composition containing the compound.
（問題点を解決するための手段）
本発明（二発明）は一般式
（上式中Ｒ１，Ｒ２はそれぞれ直鎖又は枝分れした炭素
数１〜１５のアルキル基であり、Ｊ は１又は２を示す
）で表わされるアルコキシプロピルベンゼン類および該
化合物を有効成分とする液晶組成物である。(Means for Solving the Problems) The present invention (second invention) is based on the general formula (in the above formula, R1 and R2 are each a linear or branched alkyl group having 1 to 15 carbon atoms, and J is 1 or 2) and a liquid crystal composition containing the compound as an active ingredient.
本発明の液晶組成物の成分にできる本発明の化合物以外
の他の成分としては、例えばエステル系、シッフ塩基系
、ビフェニル系、フェニルシクロヘキサン系、複素環系
等の液晶化合物をあげることができる。Other components other than the compound of the present invention that can be used as a component of the liquid crystal composition of the present invention include, for example, ester-based, Schiff base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds.
本発明の化合物の製造法は、例えば次式（ＩＩ）の反応
によって示される。A method for producing the compound of the present invention is shown, for example, by the reaction of the following formula (II).
（上式中Ｒ＋、Ｒｚ、、Ｊ、は前記に同じである）すな
わち、臭化アリルと４−アルキルシクロヘキシルフェノ
ール（、ｅ＝１）又は４−アルキルビシクロヘキシルフ
ェノール（、！ ＝ ２ ）をアセトン中炭酸カリウム
と反応を行い、フェニルアリルエーテル体とし、ついで
ジメチルアニリン中環流し、クライゼン転位して２−ア
リル−４−アルキルシクロヘキシルフェノール類を得た
。(In the above formula, R+, Rz,, J, are the same as above.) That is, allyl bromide and 4-alkylcyclohexylphenol (, e = 1) or 4-alkylbicyclohexylphenol (,! = 2) are combined with acetone. The mixture was reacted with potassium carbonate to obtain a phenylallyl ether, and then refluxed in dimethylaniline and subjected to Claisen rearrangement to obtain 2-allyl-4-alkylcyclohexylphenols.
このフェノールと臭化アルキルをアセトン中炭酸カリウ
ムと反応を行い１−アルコキシ−２−アリ−４−アルキ
ルシクロヘキシルベンゼン類を得た。これ゛をパラジウ
ム−炭素触媒を用いて接触還元を行い、目的とするアル
コキシプロピルベンゼン類を製造するか、もしくは２−
アリル−４−アルキルシクロヘキシルフェノール類をパ
ラジウム−炭素触媒を用いて接触還元を行い、２−プロ
ピル−４−シクロヘキシルフェノール類とし、これと臭
化アルキルとアセトン中、炭酸カリウムと反応を行い目
的とする化合物を得ることができる。This phenol and alkyl bromide were reacted with potassium carbonate in acetone to obtain 1-alkoxy-2-ary-4-alkylcyclohexylbenzenes. This is subjected to catalytic reduction using a palladium-carbon catalyst to produce the desired alkoxypropylbenzenes, or 2-
Allyl-4-alkylcyclohexylphenols are catalytically reduced using a palladium-carbon catalyst to produce 2-propyl-4-cyclohexylphenols, which are reacted with alkyl bromide and potassium carbonate in acetone to obtain the desired product. compound can be obtained.
（発明の効果）
本発明の化合物は他の多くの液晶化合物、すなわちエス
テル系、シッフ塩基系、ビフェニル系、フェニルシクロ
ヘキサン系、複素環系等の液晶化合物との相溶性がよく
、本発明の化合物を液晶組成物に加え、Δｎが小さく、
スしきい値電圧を低くすることができる。(Effects of the Invention) The compound of the present invention has good compatibility with many other liquid crystal compounds, such as ester-based, Schiff base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds. is added to the liquid crystal composition, Δn is small,
The threshold voltage can be lowered.
又Ｋ ｚ ／ Ｋ ＋の値を比較的大きくできるためＳ
ＴＮ型表示素子用の液晶組成物に好適な化合物であり、
又、ここで製造した１−アルキル−２−プロピル−４−
トランス−４−（トランス−４−プロピルシクロヘキシ
ル）シクロヘキシルベンゼンでアルキル基がメチル基の
ものは、スメクチック相を示し、プロピル基のものは、
スメクチックＡ相←ネマチック相→液体と相転位するの
でスメクチックＡ相を用いたレーザー書き込み型表示装
置に好適である。Also, since the value of K z / K + can be relatively large, S
A compound suitable for liquid crystal compositions for TN type display elements,
In addition, 1-alkyl-2-propyl-4- produced here
Trans-4-(trans-4-propylcyclohexyl)cyclohexylbenzene whose alkyl group is a methyl group exhibits a smectic phase, and those whose alkyl group is a methyl group exhibit a smectic phase, and those with a propyl group exhibit a smectic phase.
Since the phase transition is smectic A phase←nematic phase→liquid, it is suitable for a laser writing type display device using smectic A phase.
以下に述べる実施例により本発明の化合物につきさらに
詳細に説明する。The compounds of the present invention will be explained in more detail with reference to the following examples.
実施例１
１−ヒドロキシ−２−アリル−４−（トランス−４−プ
ロピルシクロへキシル−トランス−４−シクロヘキシル
）ベンゼンの製造
１） １−アリルオキシ−４−（トランス−４−プロピ
ルシクロへキシル−トランス−４−シクロヘキシル）ベ
ンゼンの製造
１−ヒドロキシ−４−（トランス−４−プロピルシクロ
へキシル−トランス−４−シクロヘキシル）ベンゼン３
ｇ（０，０１モル）に３００ｍスのアセトンに溶解し、
これに炭酸カリウム２０ｇを加えた。Example 1 Production of 1-hydroxy-2-allyl-4-(trans-4-propylcyclohexyl-trans-4-cyclohexyl)benzene 1) 1-allyloxy-4-(trans-4-propylcyclohexyl- Production of trans-4-cyclohexyl)benzene 1-hydroxy-4-(trans-4-propylcyclohexyl-trans-4-cyclohexyl)benzene 3
g (0.01 mol) dissolved in 300 ms of acetone,
To this was added 20 g of potassium carbonate.
反応液を５０℃にし、撹拌しながら具化アリル３．６
ｇ （０，０３ｇ）を１０分で加えた。更に２時間反応
し、ついで、８０℃にて５時間反応した。The reaction solution was heated to 50°C, and while stirring, the embodied allyl 3.6
g (0.03 g) was added in 10 minutes. The reaction was further continued for 2 hours, and then at 80°C for 5 hours.
放冷後析出した無機物と未反応物を一過した後、減圧に
てアセトンを留去した。これに水１００ ｍＪ−を加え
、析出した沈殿物をトルエン１００ｍＪ’で２回抽出し
た。 トルエン層を２Ｎ水酸化ナトリウムで洗い、つい
で中性になるまで水でトルエン層を洗った。After allowing the mixture to cool, the precipitated inorganic substances and unreacted substances were passed through, and then acetone was distilled off under reduced pressure. 100 mJ of water was added thereto, and the precipitate was extracted twice with 100 mJ' of toluene. The toluene layer was washed with 2N sodium hydroxide and then with water until neutral.
無水酸化ナトリウムでトルエン層を乾燥後、トルエンを
減圧にして留去した。残った結晶をエタノールで再結晶
を行った。融点６２℃、スメクチック−ネマチック １
５５．８℃、ネマチック−透明点 ２Ｇ２．９°Ｃ１収
量２．５ｇ （収率７３％）２）１−ヒドロキシ−２−
アリル−４−（トランス−４−プロピルシクロへキシル
−トランス−４−シクロヘキシル）ベンゼンの製造
１）で製造した１−アリルオキシ−４−（トランス−４
−プロピルシクロへキシル−トランス−４−シクロヘキ
シル）ベンゼン３．４ ｇ （０，Ｑ１モル）をＮ、
Ｎ−ジメチルアニリン１０ｍ１に溶かし、８時間窒素
雰囲気下に還流した。After drying the toluene layer with anhydrous sodium oxide, toluene was distilled off under reduced pressure. The remaining crystals were recrystallized from ethanol. Melting point 62℃, smectic-nematic 1
55.8°C, nematic clearing point 2G2.9°C1 yield 2.5g (yield 73%) 2) 1-Hydroxy-2-
Production of allyl-4-(trans-4-propylcyclohexyl-trans-4-cyclohexyl)benzene 1-allyloxy-4-(trans-4
-propylcyclohexyl-trans-4-cyclohexyl)benzene 3.4 g (0, Q1 mol) with N,
The mixture was dissolved in 10 ml of N-dimethylaniline and refluxed under nitrogen atmosphere for 8 hours.
放冷後トルエン１００ｍノ を加え、分液ロートに移し
た。６Ｎ塩酸５０ ｍＪで３回トルエン層を抽出した後
、洗液が中性になるまでトルエン層を洗った。After cooling, 100 m of toluene was added and the mixture was transferred to a separating funnel. After extracting the toluene layer three times with 50 mJ of 6N hydrochloric acid, the toluene layer was washed until the washing liquid became neutral.
トルエン層を無水硫酸ナトリウムで乾燥後Ｐ過して、減
圧でトルエン層を留去した。残った油状物をｎ−へブタ
ンで再結晶した０Ｍ点１１４〜１１６℃、収量２．５ｇ
（収率８３％）同様な°製造方法により４−（トラン
ス−４−ペンチルシクロヘキシル）フェノールから２−
アリル−４−（トランス−４−へブチルシクロヘキシル
）フェノール沸点２００℃１５−量Ｈｇを製造した。The toluene layer was dried over anhydrous sodium sulfate, filtered through P, and the toluene layer was distilled off under reduced pressure. The remaining oil was recrystallized from n-hebutane, 0M point: 114-116°C, yield: 2.5g.
(Yield 83%) From 4-(trans-4-pentylcyclohexyl)phenol to 2-
Allyl-4-(trans-4-hebutylcyclohexyl)phenol boiling point 200 DEG C. 15-amount Hg was produced.
実施例２
１−メトキシ−２−プロピル−４−〈トランス−４−プ
ロピルシクロへキシル−トランス−４−シクロヘキシル
）ベンゼンの製造
実施例１で製造した１−ヒドロキシ−２−アリル−４−
（トランス−４−プロピルシクロへキシル−トランス−
４−シクロヘキシル）ベンゼン３．４ ｇ （０，０１
モル）を３００ｍ１のアセトンに溶解し、これに炭酸カ
リウム２０ｇ加えた。Example 2 Production of 1-methoxy-2-propyl-4-<trans-4-propylcyclohexyl-trans-4-cyclohexyl)benzene 1-hydroxy-2-allyl-4- produced in Example 1
(trans-4-propylcyclohexyl-trans-
4-cyclohexyl)benzene 3.4 g (0,01
mol) was dissolved in 300 ml of acetone, and 20 g of potassium carbonate was added thereto.
反応液を５０℃にし、撹拌しながらヨウ化メチル７ｇ（
０，０５モル）を１０分で加え、７時間反応を行った。The reaction solution was heated to 50°C, and 7 g of methyl iodide (
0.05 mol) was added over 10 minutes, and the reaction was carried out for 7 hours.
放冷後析出した無機物を一過した後、減圧にてアセトン
を留去した。After allowing the mixture to cool, the precipitated inorganic substances were passed through, and then acetone was distilled off under reduced pressure.
これに水を加え、析出した油状物をトルエンで（２００
ｍ 芝）抽出した。 トルエン層を２Ｎ水酸化ナトリウ
ムで洗い、ついで中性になるまで水でトルエン層を洗っ
た。Water was added to this, and the precipitated oil was dissolved in toluene (200
m grass) extracted. The toluene layer was washed with 2N sodium hydroxide and then with water until neutral.
無水硫酸ナトリウムでトルエン層を乾燥後、トルエンを
減圧にして留去した。残った結晶をエタノールで溶かし
、強く冷却した再結晶を行った。After drying the toluene layer with anhydrous sodium sulfate, toluene was distilled off under reduced pressure. The remaining crystals were dissolved in ethanol and recrystallized under strong cooling.
室温にてスメクチックＡ、スメクチックＡ−透明点６７
．５℃。Smectic A at room temperature, Smectic A-clearing point 67
．． 5℃.
このもの１ｇを酢酸エチル５０ｍノに溶解し、パラジウ
ム−炭素触媒を加え常温常圧で接触還元を行った。水素
の吸収が止まったならば触媒を日別し、酢酸エチルを減
圧にて留去し、残った油状物をｎ−ヘプタンで再結晶を
行った。Ｃ−Ｓ点５９℃、Ｓ−１点７９．８℃収量０．
７ｇであった。1 g of this product was dissolved in 50 mL of ethyl acetate, and a palladium-carbon catalyst was added to carry out catalytic reduction at room temperature and pressure. When hydrogen absorption had ceased, the catalyst was separated, ethyl acetate was distilled off under reduced pressure, and the remaining oil was recrystallized from n-heptane. C-S point 59℃, S-1 point 79.8℃ Yield 0.
It was 7g.
実施例３〜５
実施例２においてヨウ化メチルの代りに各種の臭化アル
キルを用いて１−アルキルオキシ−２−プロピル−４−
（トランス−４−プロピルシクロへキシル−トランス−
４−シクロヘキシル）ベンゼンを又、２−プロピル−４
−（トランス−４−ヘプチルシクロヘキシル）フェノー
ルから１−アルキル−２−プロピル−４−（トランス−
４−へブチルシクロヘキシル）ベンゼンを製造した。こ
れらの結果を実施例１と共に表に示した。Examples 3 to 5 In Example 2, various alkyl bromides were used in place of methyl iodide to produce 1-alkyloxy-2-propyl-4-
(trans-4-propylcyclohexyl-trans-
4-cyclohexyl)benzene, 2-propyl-4
-(trans-4-heptylcyclohexyl)phenol to 1-alkyl-2-propyl-4-(trans-
4-Hebutylcyclohexyl)benzene was produced. These results are shown in the table together with Example 1.
応用例１
トランス−４−プロピル−（４−シアノフェニル）シク
ロヘキサン ３０重量％トランス−４−ペンチルー（
４−シアノフェニル）シクロヘキサン ４０重量％ト
ランス−４−へ１チル−（４−シアノフェニル）シクロ
ヘキサン ３０重量％なる組成の液晶混合物（Ａ）の
Ｎ−１点は５２．１℃Δεは１１．２．２０℃における
粘度は２３．４、Δｎは０．１１９ 、Ｋｓ ／に＋は
１．８２である。液晶セルとして、酸化ケイ素をコーテ
ィングし、ラビング処理した酸化スズ透明電極を有する
基板を対向させて組立てた、電極間距離が１０μｍのら
のを用意し、上記の液晶組成物（Ａ）を封入して２０℃
でその特性を測定したところ、しきい電圧（以下ｖｔｈ
と略記する）は１．５５Ｖであった。Application example 1 trans-4-propyl-(4-cyanophenyl)cyclohexane 30% by weight trans-4-pentyl(
The N-1 point of the liquid crystal mixture (A) with the composition of 40% by weight of 4-cyanophenyl)cyclohexane and 30% by weight of trans-4-hyl-(4-cyanophenyl)cyclohexane is 52.1°C Δε is 11.2 The viscosity at 20°C is 23.4, Δn is 0.119, and Ks/+ is 1.82. A liquid crystal cell was prepared by assembling substrates having transparent tin oxide electrodes coated with silicon oxide and subjected to rubbing treatment, with a distance between the electrodes of 10 μm, and the above liquid crystal composition (A) was sealed. 20℃
When we measured its characteristics, we found that the threshold voltage (hereinafter vth
) was 1.55V.
この液晶組成物（Ａ）８５重量％に本発明の実施例３で
製造した１−プロポキシ−２−プロピル−４−（）ラン
ス−４−プロピルシクロへキシル−トランス−４−シク
ロヘキシル）ベンゼン１５重量％を溶解した組成物のＮ
−１点は５３．５℃、Δεは９．５．Δｎは０．１２０
、Ｖｔｈは１．６０Ｖであった。85% by weight of this liquid crystal composition (A) was added to 15% by weight of 1-propoxy-2-propyl-4-()trans-4-propylcyclohexyl-trans-4-cyclohexyl)benzene prepared in Example 3 of the present invention. N of the composition dissolved in %
-1 point is 53.5℃, Δε is 9.5. Δn is 0.120
, Vth was 1.60V.
又に３／Ｋｌは１．８４と大きくなり又Ｎ−Ｉ点も高め
る事ができ、ＳＴＮ用としても好適である。In addition, 3/Kl is as large as 1.84, and the N-I point can also be raised, making it suitable for STN applications.
Claims (1)
炭素数１〜１５のアルキル基であり、ｌは１又は２を示
す）で表わされるアルコキシプロピルベンゼン類。 ２）一般式 ▲数式、化学式、表等があります▼・・・（ I ） （上式中Ｒ＾１、Ｒ＾２はそれぞれ直鎖又は枝分れした
炭素数１〜１５のアルキル基であり、ｌは１又は２を示
す）で表わされるアルコキシプロピルベンゼン類を少な
くとも一種類含有する液晶組成物。[Claims] 1) General formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼... (I) (In the above formula, R^1 and R^2 each represent a linear or branched carbon number of 1 to 15 alkyl group, l represents 1 or 2). 2) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the above formula, R^1 and R^2 are each a linear or branched alkyl group having 1 to 15 carbon atoms. , l represents 1 or 2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1673788A JP2514395B2 (en) | 1988-01-27 | 1988-01-27 | Liquid crystalline compound having alkyl group in side chain |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1673788A JP2514395B2 (en) | 1988-01-27 | 1988-01-27 | Liquid crystalline compound having alkyl group in side chain |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01193237A true JPH01193237A (en) | 1989-08-03 |
| JP2514395B2 JP2514395B2 (en) | 1996-07-10 |
Family
ID=11924582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1673788A Expired - Lifetime JP2514395B2 (en) | 1988-01-27 | 1988-01-27 | Liquid crystalline compound having alkyl group in side chain |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2514395B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018090569A (en) * | 2016-11-21 | 2018-06-14 | 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 ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Compound for homeotropic alignment of liquid crystal medium |
-
1988
- 1988-01-27 JP JP1673788A patent/JP2514395B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018090569A (en) * | 2016-11-21 | 2018-06-14 | 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 ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Compound for homeotropic alignment of liquid crystal medium |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2514395B2 (en) | 1996-07-10 |
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