JPH0454151A - Ester compound - Google Patents
Ester compoundInfo
- Publication number
- JPH0454151A JPH0454151A JP16610990A JP16610990A JPH0454151A JP H0454151 A JPH0454151 A JP H0454151A JP 16610990 A JP16610990 A JP 16610990A JP 16610990 A JP16610990 A JP 16610990A JP H0454151 A JPH0454151 A JP H0454151A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- expressed
- trans
- ester compound
- 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.)
- Pending
Links
- -1 Ester compound Chemical class 0.000 title claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 9
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JVORBNXKMXPLJY-UHFFFAOYSA-N C(#CC)OC1=CC=C(C=C1)O Chemical compound C(#CC)OC1=CC=C(C=C1)O JVORBNXKMXPLJY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- MGEBVSZZNFOIRB-UHFFFAOYSA-N 2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(I)=NC=2N1C1OC(CO)C(O)C1O MGEBVSZZNFOIRB-UHFFFAOYSA-N 0.000 description 1
- LZDWRJRTXSUEKQ-UHFFFAOYSA-N 3-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-3,4-dihydro-2h-pyran-4-ol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCCC1COC=CC1O LZDWRJRTXSUEKQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 210000004460 N cell Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は液晶表示装置に用いられるネマチック液晶組成
物を構成する成分として有用なエステル化合物に関する
。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an ester compound useful as a component constituting a nematic liquid crystal composition used in a liquid crystal display device.
ネマチック液晶を目の電気光学効果を利用した液晶表示
装置には動的散乱型、ゲスト・ホスト型、ねじれたネマ
チック型（ＴＮ型）、スーパーツィステッド・ネマチッ
ク型（ＳＴＮ型）など表示１５式が実用化されており、
これらのうちＴＮ型か最も広く応用されてきた。しかし
、ＴＮ型は表示の画素数に制約がありｉ［査線の数にし
て約２００本が限界であることかわかってきた。そこで
、この限界を打破する表示方式としてＳＴＮ型の液晶表
示装置が開発され実用化されつつある。There are 15 types of liquid crystal display devices using nematic liquid crystal that utilize the electro-optic effect of the eye, including dynamic scattering type, guest-host type, twisted nematic type (TN type), and super twisted nematic type (STN type). It has been put into practical use,
Of these, the TN type has been most widely applied. However, it has been found that the TN type has a restriction on the number of display pixels, and the limit is approximately 200 in terms of the number of scanning lines. Therefore, STN type liquid crystal display devices have been developed and are being put into practical use as a display method to overcome this limit.
ＴＮ型の液晶表示装置の用途としてはウォッチ、電卓、
オーディオ機器等の巾広い分野に応用されている。また
、ＳＴＮ型の液晶表示装置はワープロやパソコンのデイ
スプレィとして急速にＣＲＴに代りつつある。TN type liquid crystal display devices are used in watches, calculators,
It is applied to a wide range of fields such as audio equipment. Further, STN type liquid crystal display devices are rapidly replacing CRTs as displays for word processors and personal computers.
ＴＮ型やＳＴＮ型の液晶表示装置に用いられるネマチッ
ク液晶に求められる特性は種々あるが、それらの特性を
単一成分で満足させるようなネマチック液晶化合物は知
られていない。そこで、実用的には複数のネマチック液
晶化合物又はその類似化合物を適切な割合に混合した液
晶組成物を用いている。Although there are various characteristics required of nematic liquid crystals used in TN type and STN type liquid crystal display devices, there is no known nematic liquid crystal compound that satisfies these characteristics with a single component. Therefore, in practice, a liquid crystal composition in which a plurality of nematic liquid crystal compounds or similar compounds thereof are mixed in an appropriate ratio is used.
液晶組成物の主要な成分として従来より広く用いられて
いる次の一般式で表わされるエステル化合物は主として
ＴＮ型液晶表示装置用の液晶材料Ｒ３舎ＣＯＯ（）ｏ
Ｒ’
（ここて、Ｒ３およびＲ４はアルキル基を表わし、シク
ロヘキサン環はトランス配置である。）として大変重要
な成分であった。この化合物の長所としてはネマチック
液晶温度範囲か広く、時分割駆動方式に用いた場合に高
時分割駆動が可能であり、また製造費用か安価なとがあ
るが、また欠点としては粘性か低い割合には応答速度が
遅く、複屈折（八〇）か小さいことも欠点となりうる。The ester compound represented by the following general formula, which has been widely used as a main component of liquid crystal compositions, is mainly used as a liquid crystal material for TN type liquid crystal display devices.
It was a very important component as R' (here, R3 and R4 represent an alkyl group, and the cyclohexane ring has a trans configuration). The advantages of this compound are that it has a wide nematic liquid crystal temperature range, allows high time-division driving when used in a time-division driving system, and is inexpensive to manufacture; however, its disadvantages include viscosity and low ratio The slow response speed and low birefringence (80°) can also be disadvantages.
したがって、本発明の目的は上記の欠点である応答性を
改良し、△ｎか大きなエステル化合物を提供することに
ある。Therefore, an object of the present invention is to improve the above-mentioned drawback of responsiveness and to provide an ester compound with a large Δn.
本発明は一般式
％式％
（ここで、Ｒ’は炭素原１″−数か１〜１０のアルキル
基、Ｒ２はＨ又は炭素原ｒ数か１〜７のアルキル基、ｎ
は１〜８の整数を表わし、シクロヘキサン環はトランス
配置である。）
て表わされるエステル化合物であり、例えば次の製造方
法により得ることができる。即ち、ステップ１において
はハイドロキノン（ＩＩ）とハロケノアルキン（ＩＩＩ
）をエタノール中でナトリウムエトキシドを用いて反応
させ４−アルキニルオキシフェノール（Ｖ）を得る。ス
テップ２においてはトランス−４′ −アルキルンクロ
ヘキサンカルボニルクロライド
ム中でトリエチルアミンを用いてエステル化して本発明
のエステル化合物（Ｉ）を得る。The present invention is based on the general formula % (where R' is an alkyl group having 1"-number of carbon atoms or 1 to 10, R2 is H or an alkyl group having r number of carbon atoms or 1 to 7, n
represents an integer from 1 to 8, and the cyclohexane ring has a trans configuration. ) It is an ester compound represented by the formula, and can be obtained, for example, by the following manufacturing method. That is, in step 1, hydroquinone (II) and halochenoalkyne (III
) is reacted with sodium ethoxide in ethanol to obtain 4-alkynyloxyphenol (V). In step 2, the ester compound (I) of the present invention is obtained by esterification using triethylamine in trans-4'-alkylene chlorohexane carbonyl chloride.
スキーム
（ここで、Ｒ１は炭素原子数か１〜１０のアルキル基、
Ｒ２はＨ又は炭素原子数が１〜７のアルキル基、ｎは１
〜８の整数、ＸはＣｇ又はＢ「を表わし、シクロヘキサ
ン環はトランス配置Ｔある。）〔実 施 例〕
以下、実施例と応用例とにより本発明を更に詳細に説明
する。Scheme (where R1 is an alkyl group having 1 to 10 carbon atoms,
R2 is H or an alkyl group having 1 to 7 carbon atoms, n is 1
An integer of ~8, X represents Cg or B, and the cyclohexane ring has a trans configuration T. [Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples and Application Examples.
（実施例１）
４−プロパビニルオキシフェニル トランス４′ −ブ
ロビルンクロヘキサンカルポキンレートの製造方法。(Example 1) Method for producing 4-propavinyloxyphenyl trans 4'-brovirun clohexane carpoquinate.
ステップ１
無水エタノール２Ωにナトリウム１１ ５ｇ（０．５モ
ル）を溶解し、ヒドロキノン１１０ｇ（１．０モル）と
プロパギルブロマイド５９．５ｇ（０．５モル）を加え
１０時間還流した。エタノールを留去し、１０％ＮａＯ
Ｈ水溶液５ Ｑ Ｏ ｃｍ３を加えてからトルエンで抽
出した。水層に濃塩酸２００ｃｍ’を加えクロロホルム
で抽出し、１０％塩酸と水で洗浄した。クロロホルムを
留去し、残渣を減圧蒸留（１１７°Ｃ／１ｍｍＨｇ）し
て４−プロピニルオキシフェノール３４ｇ （０。Step 1 115 g (0.5 mol) of sodium was dissolved in 2Ω of absolute ethanol, 110 g (1.0 mol) of hydroquinone and 59.5 g (0.5 mol) of propargyl bromide were added, and the mixture was refluxed for 10 hours. Ethanol was distilled off and 10% NaO
After adding 5 Q O cm3 of an aqueous H solution, extraction was performed with toluene. 200 cm' of concentrated hydrochloric acid was added to the aqueous layer, extracted with chloroform, and washed with 10% hydrochloric acid and water. Chloroform was distilled off, and the residue was distilled under reduced pressure (117°C/1mmHg) to yield 34g (0.0%) of 4-propynyloxyphenol.
２３モル）を得た。23 mol) was obtained.
ステップ２ ４−プロピニルオキシフェノール３． ０ｇ （０。Step 2 4-Propynyloxyphenol 3. 0g (0.
０２モル）をクロロホルム３０ｃｍ’に溶解し、氷水冷
却撹拌下にトリエチルアミン３．０ｇ （０。02 mol) was dissolved in 30 cm' of chloroform, and 3.0 g (0.02 mol) of triethylamine was dissolved in 30 cm' of chloroform while cooling with ice water and stirring.
０３モル）とトランス−４−プロビルンクロヘキサン力
ルポニルクロライド３． ８ｇ （０． ０２モル
）を滴下してから室温で１晩放置した。反応液を１０％
塩酸、水、５％ＮａＯＨ水溶液、水の順序で洗浄した。03 mol) and trans-4-propylene chlorohexane, 3. 8 g (0.02 mol) was added dropwise, and the mixture was left to stand at room temperature overnight. 10% reaction solution
Washing was performed in the order of hydrochloric acid, water, 5% NaOH aqueous solution, and water.
クロロホルムを留去し、残渣をアセトンとメタノールの
混合溶媒から再結晶して４プロピニルオキシフエニル
トランス−４′プロピルシクロヘキサンカルボキンレー
ト３０ｇ１．０１モル）を得た。この化合物の融点をＤ
ＳＣを用いて測定した結果は次のとうりであった。Chloroform was distilled off, and the residue was recrystallized from a mixed solvent of acetone and methanol to obtain 4-propynyloxyphenyl.
30 g of trans-4'propylcyclohexanecarboxylate (1.01 mol) was obtained. The melting point of this compound is D
The results measured using SC were as follows.
にこれらの液晶組成物を封入して２０℃において立上り
時間τいと立下り時間τ。イを測定した。The rise time τ and fall time τ at 20° C. were measured by enclosing these liquid crystal compositions in a liquid crystal composition. A was measured.
これらの測定結果を第１表に示した。The results of these measurements are shown in Table 1.
（ここで、Ｃは結晶、■は等方性液体を表わす。）実施
例１と同様にして４−プロビニルオキンフェニル トラ
ンス−４′−ブチルシクロヘキサンカルボキシレートを
得た。この化合物の融点は次のとうりであった。(Here, C represents a crystal, and ■ represents an isotropic liquid.) In the same manner as in Example 1, 4-provinyloquinophenyl trans-4'-butylcyclohexanecarboxylate was obtained. The melting point of this compound was as follows.
（応用例１）
市販の液晶組成物ＺＬＩ−１５６５（メルク社製）に本
発明の４−プロピニルオキシフェニルトランス−４′−
ブチルシクロヘキサンカルボキシレートおよび比較とし
て４−プロピルオキシフェニル トランス−４′ −ブ
チルシクロヘキサンカルボキシレートを各々２０重量％
混合した液晶組成物を作り△ｎおよびセル厚９μｍのＴ
Ｎセル〔発明の効果〕
以上述べたように本発明の化合物を混合した液晶組成物
は△ｎか大きくて応答速度か速いことか明らかとなった
。したかって、本発明の化合物はＴＮ型およびＳＴＮ型
に用いられるネマチック液晶組成物の成分として有用で
ある。(Application Example 1) 4-Propynyloxyphenyltrans-4'- of the present invention was added to a commercially available liquid crystal composition ZLI-1565 (manufactured by Merck & Co.)
20% by weight each of butylcyclohexanecarboxylate and 4-propyloxyphenyl trans-4'-butylcyclohexanecarboxylate as a comparison.
A mixed liquid crystal composition is prepared with Δn and T with a cell thickness of 9 μm.
N Cell [Effect of the Invention] As described above, it has become clear that the liquid crystal composition containing the compound of the present invention has a large Δn and a fast response speed. Therefore, the compounds of the present invention are useful as components of nematic liquid crystal compositions used in TN and STN types.
以上 出願人 セイコーエプソン株式会社that's all Applicant: Seiko Epson Corporation
Claims (1)
、Ｒ＾２はＨ又は炭素原子数が１〜７のアルキル基、ｎ
は１〜８の整数を表わし、シクロヘキサン環はトランス
配置である。） で表わされることを特徴とするエステル化合物。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (Here, R^1 is an alkyl group having 1 to 10 carbon atoms, R^2 is H or a carbon atom number 1-7 alkyl group, n
represents an integer from 1 to 8, and the cyclohexane ring has a trans configuration. ) An ester compound characterized by being represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16610990A JPH0454151A (en) | 1990-06-25 | 1990-06-25 | Ester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16610990A JPH0454151A (en) | 1990-06-25 | 1990-06-25 | Ester compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0454151A true JPH0454151A (en) | 1992-02-21 |
Family
ID=15825189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16610990A Pending JPH0454151A (en) | 1990-06-25 | 1990-06-25 | Ester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0454151A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102781640A (en) * | 2011-02-09 | 2012-11-14 | 三菱工程塑料株式会社 | Process for production of polycarbonate resin pellets |
-
1990
- 1990-06-25 JP JP16610990A patent/JPH0454151A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102781640A (en) * | 2011-02-09 | 2012-11-14 | 三菱工程塑料株式会社 | Process for production of polycarbonate resin pellets |
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