JP2906160B2 - Tropolone compounds - Google Patents
Tropolone compoundsInfo
- Publication number
- JP2906160B2 JP2906160B2 JP2019955A JP1995590A JP2906160B2 JP 2906160 B2 JP2906160 B2 JP 2906160B2 JP 2019955 A JP2019955 A JP 2019955A JP 1995590 A JP1995590 A JP 1995590A JP 2906160 B2 JP2906160 B2 JP 2906160B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- alkyl group
- carbon atoms
- present
- 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 - Lifetime
Links
- 150000004788 tropolones Chemical class 0.000 title description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 17
- -1 Tropolone compound Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- MDYOLVRUBBJPFM-UHFFFAOYSA-N Tropolone Natural products OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 description 24
- 239000004990 Smectic liquid crystal Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RHKLONPUIWSHCD-UHFFFAOYSA-N 4,5-dihydroxycyclohepta-2,4,6-trien-1-one Chemical compound OC=1C=CC(=O)C=CC=1O RHKLONPUIWSHCD-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明はトロポロン化合物、該化合物を含む液晶組成
物、およびそれを利用した液晶素子に関する。Description: TECHNICAL FIELD The present invention relates to a tropolone compound, a liquid crystal composition containing the compound, and a liquid crystal device using the same.
トロポロン誘導体は、非ベンゼン系芳香族化合物の代
表的な化合物として、興味ある研究対象とされ、多くの
化合物で合成されている。しかし、これらの化合物が実
用された例はあまり知られていない。The tropolone derivative is an interesting research object as a typical non-benzene-based aromatic compound, and has been synthesized by many compounds. However, few practical examples of these compounds have been known.
近年、液晶の研究がさかんとなり、数多くの液晶化合
物が合成されている。従来、液晶が見い出された化合物
系は最低限、５員環あるいは６員環を２個以上含むもの
である。たとえば、次式で示されるような化合物が知ら
れている。In recent years, research on liquid crystals has become active, and many liquid crystal compounds have been synthesized. Conventionally, compound systems in which liquid crystals have been found contain at least two or more 5- or 6-membered rings. For example, a compound represented by the following formula is known.
（ここでR,R′はアルキル基、アルコキシ基などを表
す。）例外的には、一般式 で示すような化合物が単環にて液晶を示すことが知られ
ているが、これは、式 のように、２量体を形成していて、実は３つの環として
作用していると考えられている。また、式 で表されるような化合物が、ディスコテック液晶と呼ば
れる液晶状態を示すことが知られているが、このような
化合物は、ネマチック、スメクチック等の液晶化合物と
ははっきりと一線を画すものである。 (Where R and R ′ represent an alkyl group, an alkoxy group, etc.) It is known that a compound such as shown in the following shows a liquid crystal in a single ring. It is thought that they form a dimer and actually act as three rings. Also, the formula Is known to exhibit a liquid crystal state called discotec liquid crystal, but such a compound is clearly different from liquid crystal compounds such as nematic and smectic.
このように、単環化合物で液晶状態を呈するものはほ
とんどない。Thus, almost no monocyclic compound exhibits a liquid crystal state.
本発明者らは、トロポロン化合物の実用化について研
究を重ねた結果、７員環の単環化合物である新規なトロ
ポロン化合物を合成することに成功し、さらに該化合物
が液晶状態を示すことを見出し、本発明を完成するにい
たった。As a result of repeated studies on the practical use of tropolone compounds, the present inventors have succeeded in synthesizing a novel tropolone compound which is a 7-membered monocyclic compound, and have found that the compound exhibits a liquid crystal state. The present invention has been completed.
すなわち、本発明の目的は、単環化合物で液晶状態を
示す化合物を提供することであり、さらに該化合物を含
む液晶組成物、液晶素子を提供することである。That is, an object of the present invention is to provide a compound having a liquid crystal state as a monocyclic compound, and to further provide a liquid crystal composition and a liquid crystal element containing the compound.
本発明のトロポロン化合物は、一般式 （ここで、R1は、炭素数２〜20のアルキル基、R2は、炭
素数２〜20のアルキル基を示す）で表わされる５−アル
コキシ−２−アルカノイルオキシトロポンであることを
特徴とする。The tropolone compound of the present invention has the general formula (Here, R 1 represents an alkyl group having 2 to 20 carbon atoms, and R 2 represents an alkyl group having 2 to 20 carbon atoms), which is a 5-alkoxy-2-alkanoyloxytropone represented by the following formula: And
本発明の液晶組成物は、（Ｉ）式で表される５−アル
コキシ−２−アルカノイルオキシトロポンを少なくとも
一種含有することを特徴とする。The liquid crystal composition of the present invention is characterized by containing at least one 5-alkoxy-2-alkanoyloxytropone represented by the formula (I).
本発明の液晶素子は、（Ｉ）式で表わされる５−アル
コキシ−２−アルカノイルオキシトロポンを少なくとも
一種含有する液晶組成物を使用して構成されることを特
徴とする。The liquid crystal element of the present invention is characterized by being constituted by using a liquid crystal composition containing at least one 5-alkoxy-2-alkanoyloxytropone represented by the formula (I).
本発明のトロポロン化合物の一般式（Ｉ）において、
好ましいR1としては、炭素数８〜20のアルキル基、より
好ましくは炭素数12〜18のアルキル基であるが、これら
は、メチル分岐、エチル分岐等を１個以上含んでいるこ
とも可能であり、また、R1は光学活性基の場合もあり得
る。また、好ましいR2としては、炭素数６〜18のアルキ
ル基であり、より好ましくは炭素数７〜13のアルキル基
であるが、これらは、メチル分岐、エチル分岐等を１個
以上含んでいることも可能である。また、R2は光学活性
基の場合もあり得る。In the general formula (I) of the tropolone compound of the present invention,
Preferred R 1 is an alkyl group having 8 to 20 carbon atoms, more preferably an alkyl group having 12 to 18 carbon atoms, and these may include one or more methyl branches, ethyl branches and the like. Yes, and R 1 can be an optically active group. Further, preferred R 2 is an alkyl group having 6 to 18 carbon atoms, more preferably an alkyl group having 7 to 13 carbon atoms, which contains at least one methyl branch, ethyl branch and the like. It is also possible. R 2 may be an optically active group.
本発明のトロポロン化合物は、つぎに示す経路で製造
することができる。The tropolone compound of the present invention can be produced by the following route.
すなわち、５−ヒドロキシトロポロン（１）にアルキ
ルブロミド（R1Br）を作用させ５−アルコキシトロポロ
ン（２）とし、これにアルカノイルクロリド（R2COCl）
を作用させ５−アルコキシ−２−アルカノイルオキシト
ロポン（Ｉ）を製造する。 That is, an alkyl bromide (R 1 Br) is allowed to act on 5-hydroxytropolone ( 1 ) to form a 5-alkoxytropolone ( 2 ), which is then treated with alkanoyl chloride (R 2 COCl).
To produce 5-alkoxy-2-alkanoyloxytropone (I).
本発明のトロポロン化合物は、液晶特にスメクチック
Ａ相を呈する。スメクチックＡ相は、熱による分子配列
を制御することにより、光を散乱、透過の２状態に変化
させることができるので熱書込表示〔たとえば、苗村；
第10回液晶討論会13A10（1984）〕また、レーザービー
ム書込と呼ばれるレーザを使用するアドレッシングも可
能である。あるいは、動的散乱と呼ばれる方式〔たとえ
ば、F.Dazai,T.Uchida and N.Wada.Mol.Cryst.Liqu Cry
st.,34（1977）197〕においても使用可能である。The tropolone compound of the present invention exhibits a liquid crystal, particularly a smectic A phase. The smectic A phase can change light into two states, scattering and transmission, by controlling molecular arrangement by heat.
The 10th Liquid Crystal Symposium 13A10 (1984)] Also, addressing using a laser called laser beam writing is possible. Alternatively, a method called dynamic scattering (for example, F. Dazai, T. Uchida and N. Wada. Mol. Cryst. Liqu Cry
st., 34 (1977) 197].
これらの表示方式においては、広い温度領域に渡って
スメクチックＡを呈することが条件としてあげられるの
で、本発明の化合物がこれらの条件を好適にみたすもの
である。In these display systems, the condition is to exhibit smectic A over a wide temperature range, and the compound of the present invention suitably satisfies these conditions.
強誘電性液晶〔Clark ら;Applied Phys.lett.,36,899
（1980）〕において、スメクチックＡの存在は配向制御
のために大きな役割をはたすことが（第11回液晶討論会
予稿集2N25）で報告されている。この場合、表示体（デ
ィスプレー）作製にあたって、カイラルスメクチックＣ
相の高温側に、スメクチックＡを有しない組成物は配向
性が著しく悪いことが経験的に判明している。Ferroelectric liquid crystal (Clark et al .; Applied Phys.lett., 36 , 899)
(1980)] reported that the presence of smectic A plays a large role in controlling the alignment (Preliminary Report of the 11th Liquid Crystal Symposium 2N25). In this case, chiral smectic C
It has been empirically found that compositions without smectic A on the hot side of the phase have significantly poor orientation.
そこで、このような組成物に対して、著しく広いスメ
クチックＡ相を有する本発明のトロポロン化合物を添加
することにより、スメクチックＡ相を誘起させ、安定な
配向が得られるスメクチックＡ相を有する強誘電性液晶
組成物を得ることができる。Therefore, by adding a tropolone compound of the present invention having a remarkably wide smectic A phase to such a composition, a smectic A phase is induced, and a ferroelectric substance having a smectic A phase from which a stable orientation is obtained. A liquid crystal composition can be obtained.
以下、実施例に従って本発明の化合物、および組成物
を詳しく説明する。Hereinafter, the compounds and compositions of the present invention will be described in detail with reference to Examples.
実施例１ ５−ペンタデシルオキシ−２−デカノイルオキシ−ト
ロポン（（Ｉ）式においてR1＝ｎ−C15H31，R2＝ｎ−C9
H19の化合物）の製造 （ｉ）５−ペンタデシルオキシ・トロポロンの製造 氷冷下、水素化ナトリウム（油性55％）300mgにヘキ
サメチルホスホルアミド10mlを加えた。これに５−ヒド
ロキシトロポロン750mgを加え15分攪拌した。これに１
−ブロモペンタデカン1.6mlを加えて室温にて12時間攪
拌し反応を行なった。反応後、反応液を2N塩酸50ml中に
移しこれを酢酸エチルで抽出した。有機層を水洗のの
ち、乾燥し、溶媒を留去した。残分を酢酸エチルを用い
て再結晶して５−ペンタデシルオキシトロポロンを得
た。Example 1 5-pentadecyloxy-2-decanoyloxy-tropone (in the formula (I), R 1 = n-C 15 H 31 , R 2 = n-C 9
Compound) manufacturing (i) 5-prepared ice cooling under pentadecyloxy-tropolone H 19, was added hexamethylphosphoramide 10ml sodium hydride (55% in oil) 300 mg. To this, 750 mg of 5-hydroxytropolone was added and stirred for 15 minutes. This one
1.6 mL of -bromopentadecane was added, and the mixture was stirred at room temperature for 12 hours to carry out a reaction. After the reaction, the reaction solution was transferred into 50 ml of 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried, and the solvent was distilled off. The residue was recrystallized from ethyl acetate to obtain 5-pentadecyloxytropolone.
（ii）標題化合物の製造 （ｉ）で製造した５−ペンタデシルオキシトロポロン
70mgとピリジン3ml、デカノイルクロリド0.04ml、及び
４−ジメチルアミノピリジン5mgを加え、室温下で12時
間攪拌し、反応を行なった。反応後、反応液を水100ml
へ投入し、この液を酢酸エチルで抽出し、有機層を水洗
ののち、乾燥し、溶媒を留去した。残分を、シリカゲル
クロマトグラフィー（溶離液酢酸エチル）にて精製して
標題の５−ペンタデシルオキシ−２−デカノイルオキシ
トロポロンを得た。(Ii) Production of the title compound 5-pentadecyloxytropolone produced in (i)
70 mg, 3 ml of pyridine, 0.04 ml of decanoyl chloride and 5 mg of 4-dimethylaminopyridine were added, and the mixture was stirred at room temperature for 12 hours to carry out a reaction. After the reaction, add 100 ml of water to the reaction solution.
The solution was extracted with ethyl acetate, the organic layer was washed with water, dried, and the solvent was distilled off. The residue was purified by silica gel chromatography (eluent: ethyl acetate) to give the title 5-pentadecyloxy-2-decanoyloxytropolone.
この化合物はCr・48（・SA47）・ISOの相転移を示し
た。This compound showed a phase transition of Cr · 48 (· S A 47) · ISO .
元素分析値はC32H54O4として計算値:C76.45点H10.83,実
測値:C76.50,H10.95であった。Elemental analysis: C 32 H 54 O 4 Calculated: C 76.45, point H 10.83; actual values: C 76.50, H 10.95.
IR,MS,NMRの測定結果は下記のとおりである。 The measurement results of IR, MS, and NMR are as follows.
IR（KBr,Disc） ν:2970,2930,2850,1740,1630,1590,1570,1530,1520,14
70,1450,1400,1370,1320,1260,1210,1180,1100,860,720
cm-1 MS:m/z 502（M+−１）,503（M+）,504（M+＋１）1 H−NMR（CDCl3） δ:0.88（6H,t,J＝6.6Hz）,1.2〜1.5（36H,m）,1.77（4
H,m）,2.59（2H,t,J＝7.5Hz）,3.91（2H,t,J＝6.6Hz）,
6.6（2H,brs）,7.14（2H,d,J＝12.1Hz）13 C−NMR（CD Cl3） δ:14.1,22.7,24.9,26.0,28.8,29.1,29.3,29.37,29.44,
29.5,29.6,29.7,31.9,32.0,34.0,68.8,163.0,171.5 実施例２〜11 実施例１と同様にして、実施例２〜11の化合物を製造
した。このようにして製造した化合物の相転移温度を実
施例１の化合物とまとめて表１に示す。IR (KBr, Disc) ν: 2970,2930,2850,1740,1630,1590,1570,1530,1520,14
70,1450,1400,1370,1320,1260,1210,1180,1100,860,720
cm -1 MS: m / z 502 (M + -1), 503 (M + ), 504 (M + +1) 1 H-NMR (CDCl 3 ) δ: 0.88 (6H, t, J = 6.6 Hz), 1.2 to 1.5 (36H, m), 1.77 (4
H, m), 2.59 (2H, t, J = 7.5Hz), 3.91 (2H, t, J = 6.6Hz),
6.6 (2H, brs), 7.14 (2H, d, J = 12.1 Hz) 13 C-NMR (CD Cl 3 ) δ: 14.1, 22.7, 24.9, 26.0, 28.8, 29.1, 29.3, 29.37, 29.44,
29.5, 29.6, 29.7, 31.9, 32.0, 34.0, 68.8, 163.0, 171.5 Examples 2 to 11 In the same manner as in Example 1, the compounds of Examples 2 to 11 were produced. Table 1 shows the phase transition temperatures of the compounds thus produced together with the compounds of Example 1.
実施例12（使用例） 実施例1,4および９で得られた以下の化合物を等量混
合し、液晶組成物を調製した。 Example 12 (Using Example) The following compounds obtained in Examples 1, 4 and 9 were mixed in equal amounts to prepare a liquid crystal composition.
この組成物の融点は明瞭ではないがSA 48 ISOの相転
移温度を示した。 Although the melting point of this composition was not clear, it showed the phase transition temperature of S A 48 ISO .
本発明のトロポロン化合物は、新規な化合物であり、
また、単環化合物で液晶状態を示すことが大きな特徴で
ある。The tropolone compound of the present invention is a novel compound,
Another major feature is that the monocyclic compound exhibits a liquid crystal state.
他の液晶化合物との相溶性を向上させ、液晶組成物の
粘性を低下させ応答速度を向上させ得る特徴をもつ、特
にスメクチック状態を示すため、液晶状態の複屈折等の
異方性を利用することによって、種々の液晶素子に適用
することが可能である。It has the feature of improving the compatibility with other liquid crystal compounds, reducing the viscosity of the liquid crystal composition and improving the response speed, and in particular uses the anisotropy such as birefringence of the liquid crystal state to show a smectic state. Thereby, it can be applied to various liquid crystal elements.
本発明の液晶組成物は、単環化合物を含有することが
大きな特徴であり、著しい広いスメクチックＡ相を有す
る本発明の化合物を含有するために安定な配向が得られ
るスメクチックＡ相を有する。The liquid crystal composition of the present invention is characterized by containing a monocyclic compound, and has a remarkably wide smectic A phase. The liquid crystal composition has a smectic A phase in which stable alignment can be obtained because of containing the compound of the present invention.
本発明の液晶素子は、広い温度領域にわたってスメク
チックＡを呈することができる。The liquid crystal element of the present invention can exhibit smectic A over a wide temperature range.
Claims (3)
素数２〜20のアルキル基を示す）で表わされる５−アル
コキシ−２−アルカノイルオキシトロポンであることを
特徴とするトロポロン化合物。(1) General formula (Here, R 1 represents an alkyl group having 2 to 20 carbon atoms, and R 2 represents an alkyl group having 2 to 20 carbon atoms), which is a 5-alkoxy-2-alkanoyloxytropone represented by the following formula: Tropolone compound.
素数２〜20のアルキル基を示す）で表わされる５−アル
コキシ−２−アルカノイルオキシトロポンを少なくとも
一種含有することを特徴とした液晶組成物。2. The general formula (Where R 1 represents an alkyl group having 2 to 20 carbon atoms, and R 2 represents an alkyl group having 2 to 20 carbon atoms) containing at least one 5-alkoxy-2-alkanoyloxytropone represented by the following formula: A liquid crystal composition comprising:
素数２〜20のアルキル基を示す）で表わされる５−アル
コキシ−２−アルカノイルオキシトロポンを少なくとも
一種含有する液晶組成物を使用して構成された液晶素
子。3. The general formula (Where R 1 represents an alkyl group having 2 to 20 carbon atoms, and R 2 represents an alkyl group having 2 to 20 carbon atoms) containing at least one 5-alkoxy-2-alkanoyloxytropone represented by the following formula: A liquid crystal element formed using a liquid crystal composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019955A JP2906160B2 (en) | 1990-01-30 | 1990-01-30 | Tropolone compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019955A JP2906160B2 (en) | 1990-01-30 | 1990-01-30 | Tropolone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03227957A JPH03227957A (en) | 1991-10-08 |
| JP2906160B2 true JP2906160B2 (en) | 1999-06-14 |
Family
ID=12013622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019955A Expired - Lifetime JP2906160B2 (en) | 1990-01-30 | 1990-01-30 | Tropolone compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2906160B2 (en) |
-
1990
- 1990-01-30 JP JP2019955A patent/JP2906160B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Ｂｕｌｌ．Ｃｈｅｍ．Ｓｏｃ．Ｊｐｎ．（１９８７）６０（１２），４３３５−８ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03227957A (en) | 1991-10-08 |
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