JPS61140558A - Acid azide derivative - Google Patents
Acid azide derivativeInfo
- Publication number
- JPS61140558A JPS61140558A JP59261370A JP26137084A JPS61140558A JP S61140558 A JPS61140558 A JP S61140558A JP 59261370 A JP59261370 A JP 59261370A JP 26137084 A JP26137084 A JP 26137084A JP S61140558 A JPS61140558 A JP S61140558A
- Authority
- JP
- Japan
- Prior art keywords
- formulas
- tables
- mathematical
- liquid crystal
- chemical
- 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
- 239000002253 acid Substances 0.000 title claims description 8
- 150000001540 azides Chemical class 0.000 title claims description 8
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 abstract description 20
- -1 benzoic acic azide Chemical class 0.000 abstract description 8
- 239000013078 crystal Substances 0.000 abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 235000010290 biphenyl Nutrition 0.000 abstract description 2
- 239000004305 biphenyl Substances 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- PJHUABJTDFXYRQ-UHFFFAOYSA-N benzoyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CC=CC=C1 PJHUABJTDFXYRQ-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（発明の目的）
本発明は新規な液晶化合物である酸アジド銹導体および
該化合物を含有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Objects of the Invention) The present invention relates to a novel liquid crystal compound, an acid azide conductor, and a liquid crystal composition containing the compound.
液晶を使用した表示素子は時計、電卓などに広も
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シ、液
晶相にはネマチック相、スメクチック相、コレステリッ
ク相があり、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ている。それらＫはＴＮ型（ねじれ
ネマチック型）、ｎ５ｆｆｉ（動的散乱製）、ゲスト・
ホスト型、ＤＡＰ型などがあシ、それぞれに使用される
液晶化合物に要求される性質唸異る。しかし、いずれに
してもこれら表示素子に使用される液晶化合物はなるべ
く広い温度範囲で液晶相を示すものが望ましく、また、
水分、光、熱、空気等に対しても安定であることが要求
されている。しかし現在のところ単一の化合物でそのよ
りな条件をナベてみたすようなものはなく、数種の液晶
化合物または液晶類似化合物を混合して実用に供してい
るのが現状であるＯ
本発明の目的は上記のような目的に使用される液晶組成
物の成分として有用な液晶化合物および組成物を提供す
ることにある。Display elements using liquid crystals are widely used in watches, calculators, etc. These liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and the liquid crystal phases include a nematic phase, a smectic phase, and a cholesteric phase, among which those using nematic liquid crystal are the most It has been widely put into practical use. These K are TN type (twisted nematic type), n5ffi (manufactured by Dynamic Scattering), guest・
There are host type, DAP type, etc., and the properties required of the liquid crystal compound used for each type are different. However, in any case, it is desirable that the liquid crystal compounds used in these display elements exhibit a liquid crystal phase over as wide a temperature range as possible, and
It is also required to be stable against moisture, light, heat, air, etc. However, at present, there is no single compound that satisfies all of these conditions, and the present invention is to mix several types of liquid crystal compounds or liquid crystal-like compounds for practical use. The object is to provide liquid crystal compounds and compositions useful as components of liquid crystal compositions used for the above purposes.
（発明の構成）
本発明は、一般式
（（■）式中、Ｒは炭素数１〜１５のアルキル基、アル
コキシ基またはアルコキシメチル基を示し、環（弘また
は舎は→！刈、べ＝Ｘ、（（、示し、１Ｆｉｘｔたは２
の整数を示す。）で表わされる酸アジド誘導体および該
化合物を少くとも１種含有する液晶組成物である。(Structure of the Invention) The present invention relates to a general formula ((■) in which R represents an alkyl group, an alkoxy group, or an alkoxymethyl group having 1 to 15 carbon atoms, and a ring (Hiroshi or Sha is →!Kari, Be= X, ((, indicates, 1Fixt or 2
indicates an integer. ) and a liquid crystal composition containing at least one kind of the compound.
本発明の化合物としては、４−（）ランス−４−グロビ
ルシクロヘキシル）安息香酸アジド、４−（）：ｙンス
ー４−ペンチルシクロヘキシル）安息香酸アジド、４−
（）？ンスー４−ヘプチルシクロヘキシル）安息香酸ア
ジド、４−（）ランス−４−メトキシメチルシフ目ヘキ
シル）安息香酸アジド、４−（）ランス−４−エトキシ
メチルシクロへ中シル）安息香波アジドなどの４−（ト
ランス−置換シクロヘキクル）安息香酸アジド、４−ペ
ンチルビフェニリル−４１−カルボン酸アジド、４−へ
キシルビフェニリル−４′−カルボン酸アジド、４−へ
ブチルビフェニリル−４′−カルボン酸アジドなどの４
−（ｐ−置換フェニル）安息香酸アジド、訃よびトラン
ス−４−（トランス−４−置換シクロヘキシル）シクロ
ヘキサン力）ｖボン酸アジド等のほかにトランス−４−
（ｐ−置ｔｌ＋フェニル）シクロヘキサンカルボン酸ア
ジドを挙げることができる。Compounds of the present invention include 4-()trans-4-globylcyclohexyl)benzoic acid azide, 4-():yinsu-4-pentylcyclohexyl)benzoic acid azide, 4-
()? 4-(4-heptylcyclohexyl)benzoic acid azide, 4-()trans-4-methoxymethylcyclohexyl)benzoic acid azide, 4-()trans-4-ethoxymethylcyclohexyl)benzoic acid azide, etc. (trans-substituted cyclohexyl)benzoic acid azide, 4-pentylbiphenyl-41-carboxylic acid azide, 4-hexylbiphenyl-4'-carboxylic acid azide, 4-hebutylbiphenyl-4'-carboxylic acid azide etc. 4
In addition to -(p-substituted phenyl)benzoic acid azide, trans-4-(trans-4-substituted cyclohexyl)cyclohexane) v-bonic acid azide, etc.
Mention may be made of (p-tl+phenyl)cyclohexanecarboxylic acid azide.
本発明の化合物の製造法を示すと、目的物に対応したカ
ルボン酸クロリドに、アセトン、ジオキサン、テトラヒ
ドロフラン等の有機溶媒中でアジ化ナトリウムの水溶液
を反応させて目的の酸アジド誘導体とする。これを式で
示すと
（上式中、ｕＸ％、舎およびｌは前記に同じ。）と表わ
される。The method for producing the compound of the present invention is to react a carboxylic acid chloride corresponding to the desired product with an aqueous solution of sodium azide in an organic solvent such as acetone, dioxane, or tetrahydrofuran to obtain the desired acid azide derivative. This can be expressed as a formula (in the above formula, uX%, y and l are the same as above).
本発明の液晶組成物は（１）式で示される本発明の酸ア
ジド誘導体を、好ましくは１〜３０重量％、よシ好まし
くは５〜２０重量％含有することを特徴とする。The liquid crystal composition of the present invention is characterized by containing preferably 1 to 30% by weight, more preferably 5 to 20% by weight of the acid azide derivative of the present invention represented by formula (1).
（発明の効果）
本発明の化合物は他の液晶化合物、例えばビフェニル系
、エステル系、シック系、フェニルシクロヘキサン系、
アゾキシ系、複素環系等の液晶との相溶性にすぐれてお
り、また室温付近から高温まで幅広い液晶温度範囲を有
している。さらに本発明の化合物は粘度が極めて低いた
めに、本発明の化合物を使用する事によシ得られた組成
物の液晶温度範囲を広げかつ粘度を低下させる効果は大
である。(Effect of the invention) The compound of the present invention can be used with other liquid crystal compounds, such as biphenyl-based, ester-based, chic-based, phenylcyclohexane-based,
It has excellent compatibility with azoxy-based and heterocyclic-based liquid crystals, and has a wide liquid crystal temperature range from around room temperature to high temperatures. Further, since the compound of the present invention has an extremely low viscosity, the use of the compound of the present invention has a great effect of widening the liquid crystal temperature range and lowering the viscosity of the composition obtained.
（実施例）
以下に実施例により、本発明をさらに詳しく説明するが
、本発明はこれらの例に限定されるものではない。(Examples) The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples.
実施例１
４−（）ランス−４−グロビルシクロヘキシル）安息香
酸アジドの製造
公知の方法で得られた４−（トランス−４−プロビルシ
クロヘキシルク安息香酸クロリド６ｔ（２２，６ミルモ
ル）をアセト７３０ ＣＣに５〜ｌｏ℃にて撹拌懸濁さ
せているとζろへ、アジ化ナトリウム１．８ ｔ （２
７，０ミリモル）を水１０ＣＣに溶解した溶液を１０℃
以下で加え、１０〜１５℃で５時間撹拌し、反応させた
後に反応液を水２００ ＣＣに加えた。ここで析出した
結晶を一過し、水洗後、乾燥した。これをエチルアルコ
ール２０ＣＣから再結晶を行い、目的物である４−（ト
ランス−４−プロピルシクロへ中シル）安息香酸アジド
４．２Ｆ４３．５℃、ネｉチック相−等方性液相転移点
（Ｎ−１点と略す）はｌ Ｏ３，２℃であった。Example 1 Production of 4-()trans-4-globylcyclohexyl)benzoic acid azide 6t (22.6 mmol) of 4-(trans-4-propylcyclohexylbenzoic acid chloride) obtained by a known method was dissolved in acetate. While stirring and suspending in 730 CC at 5~lo℃, 1.8 t (2
A solution of 7.0 mmol) dissolved in 10 cc of water was heated at 10°C.
The reaction solution was added to 200 cc of water after stirring at 10-15° C. for 5 hours and reacting. The precipitated crystals were filtered out, washed with water, and then dried. This was recrystallized from 20 cc of ethyl alcohol to produce the target product, 4-(trans-4-propylcyclosil)benzoic acid azide, at 4.2 F, 43.5° C., and the transition point between natural phase and isotropic liquid phase. (abbreviated as point N-1) was lO3.2°C.
実施例２．３
実施例ＩＫ準じて、それぞれ対応するカルボン酸クロリ
ドから目的の酸アジドを製造し丸。これらの相転移温度
を次に記す。Example 2.3 According to Example IK, the desired acid azides were prepared from the corresponding carboxylic acid chlorides. These phase transition temperatures are described below.
４−（）ｊンスー４−メトキシメチルシクロヘキシル）
安息香酸アジド
Ｃ−Ｎ点： ４６．５℃
Ｎ−Ｉ点： ９３．７℃
４−ペンチルビフェニリル−４′−カルボン酸アジド
Ｃ−Ｎ点： ９０．ｌｔｌ：
Ｎ−Ｉ点：ｌＯｌ、６℃
実施例４
なる液晶組成物（Ａ）のＮ−１点は５２℃、誘電率の異
方性Δεは１１．２．２０℃における粘度は２３．４
ｃｐであった。この液晶組成物（Ａ） ８５重量−に実
施例１で製造した４−（）、Ｆンスー４−プロピル７ク
ロヘキシル）安息香酸アジド１５重量−を加えた液晶組
成物のＮ−Ｉ点は６０．０℃、Δεは１２．１であった
。また２０℃における粘度は２０．７ ｅｐと低下した
。4-(4-methoxymethylcyclohexyl)
Benzoic acid azide C-N point: 46.5°C N-I point: 93.7°C 4-pentylbiphenyl-4'-carboxylic acid azide C-N point: 90. ltl: N-I point: lOl, 6°C Example 4 The N-1 point of the liquid crystal composition (A) is 52°C, the dielectric constant anisotropy Δε is 11.2, and the viscosity at 20°C is 23.4.
It was cp. The N-I point of the liquid crystal composition obtained by adding 15 weight of the 4-(),Fn-4-propyl-7chlorohexyl)benzoic acid azide prepared in Example 1 to 85 weight of this liquid crystal composition (A) was 60. At 0°C, Δε was 12.1. In addition, the viscosity at 20° C. decreased to 20.7 ep.
この様に本発明の化合物を使用する事によシ得られた販
晶組成物の液晶温度範囲を広けかつ組成物の粘度を低下
させる効果は著しい。As described above, the use of the compound of the present invention has a remarkable effect of widening the liquid crystal temperature range of the commercially available crystal composition and lowering the viscosity of the composition.
以上that's all
Claims (2)
基またはアルコキシメチル基を示し、環▲数式、化学式
、表等があります▼または▲数式、化学式、表等があり
ます▼は▲数式、化学式、表等があります▼、▲数式、
化学式、表等があります▼、▲数式、化学式、表等があ
ります▼、▲数式、化学式、表等があります▼、▲数式
、化学式、表等があります▼、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼ または▲数式、化学式、表等があります▼を示し、ｌは
１または２の整数を示す。）で表わされる酸アジド誘導
体。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents an alkyl group, alkoxy group, or alkoxymethyl group with 1 to 150 carbon atoms, and the ring ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. Indicates ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and l indicates an integer of 1 or 2. ) Acid azide derivatives represented by
基またはアルコキシメチル基を示し、環▲数式、化学式
、表等があります▼または▲数式、化学式、表等があり
ます▼は▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼、▲数式、化学式
、表等があります▼、▲数式、化学式、表等があります
▼または▲数式、化学式、表等があります▼を示し、ｌ
は１または２の整数を示す。）で表わされる酸アジド誘
導体を少くとも１種含有することを特徴とする液晶組成
物。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents an alkyl group, alkoxy group, or alkoxymethyl group having 1 to 15 carbon atoms, and the ring ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ,
represents an integer of 1 or 2. ) A liquid crystal composition comprising at least one acid azide derivative represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59261370A JPS61140558A (en) | 1984-12-11 | 1984-12-11 | Acid azide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59261370A JPS61140558A (en) | 1984-12-11 | 1984-12-11 | Acid azide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61140558A true JPS61140558A (en) | 1986-06-27 |
| JPH0481980B2 JPH0481980B2 (en) | 1992-12-25 |
Family
ID=17360894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59261370A Granted JPS61140558A (en) | 1984-12-11 | 1984-12-11 | Acid azide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61140558A (en) |
-
1984
- 1984-12-11 JP JP59261370A patent/JPS61140558A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0481980B2 (en) | 1992-12-25 |
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