JPH0311039A - Novel aromatic arboxylic acid ester compound - Google Patents
Novel aromatic arboxylic acid ester compoundInfo
- Publication number
- JPH0311039A JPH0311039A JP14277489A JP14277489A JPH0311039A JP H0311039 A JPH0311039 A JP H0311039A JP 14277489 A JP14277489 A JP 14277489A JP 14277489 A JP14277489 A JP 14277489A JP H0311039 A JPH0311039 A JP H0311039A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- ester compound
- ring
- acid ester
- benzene ring
- 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
- 239000002253 acid Substances 0.000 title abstract description 4
- -1 ester compound Chemical class 0.000 title description 7
- 125000003118 aryl group Chemical group 0.000 title 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 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 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000017105 transposition Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 150000002148 esters Chemical class 0.000 abstract description 4
- 239000005711 Benzoic acid Substances 0.000 abstract description 3
- 235000010233 benzoic acid Nutrition 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012769 display material Substances 0.000 abstract description 2
- 239000011344 liquid material Substances 0.000 abstract 2
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000004973 liquid crystal related substance Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 4
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、電気光学的表示材料として有用なイソプロピ
ルフェニルエステル化合物に関し、さらに詳しくは、Ｔ
Ｎ型液晶材料に混合することによって液晶材料の屈折率
の異方性を大きくするに有用なイソプロピルフェニルエ
ステル化合物に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to isopropylphenyl ester compounds useful as electro-optic display materials, and more particularly, to
The present invention relates to an isopropylphenyl ester compound useful for increasing the anisotropy of the refractive index of a liquid crystal material by mixing it with an N-type liquid crystal material.
現在、ＴＮ型液晶セルはグリーンまたはブルーモードよ
り白黒、カラー化へ向けて開発が進められており、それ
と併行して動画対応への高、速応答化の検討が進められ
ている。高速応答としては、従来、強誘電性液晶が研究
されているが、ＴＮ型液晶セルの層の厚さをより薄くす
ることにより、高速応答が期待される。その場合、セル
に充填される液晶材料の屈折率の異方性（Δｎ）の大き
な液晶材料が必要となる。Currently, TN-type liquid crystal cells are being developed from green or blue modes to black and white and color, and at the same time, studies are underway to improve response times to support moving images. As for high-speed response, ferroelectric liquid crystals have been studied so far, but high-speed response is expected by making the layer thickness of the TN type liquid crystal cell thinner. In that case, a liquid crystal material with a large refractive index anisotropy (Δn) is required to fill the cell.
本発明者等は、上記現状に鑑み、低粘度にして高いΔｎ
を示す化合物を見出すべく鋭意検討を重ねた結果、次の
一般式（Ｉ）で表される新規なイソプロピルフェニルエ
ステル化合物を液晶に添加することにより、液晶のΔｎ
を著しく改良することを見出した。In view of the above-mentioned current situation, the inventors of the present invention have developed a method that has a low viscosity and a high Δn.
As a result of intensive studies to find a compound that exhibits
was found to significantly improve.
シル環を示し、この環と隣接するベンゼン環はトランス
の位置にある。Ｒは水素原子または炭素原子数１〜１２
のアルキル基を示す、）
本発明になる上記−数式（Ｉ）で表される化合物におい
て、Ｒで示される炭素原子数１−１２のアルキル基とし
ては、例えば、メチル、エチル、プロピル、ブチル、ペ
ンチル、ヘキシル、ヘプチル、オクチル、ノニル、デシ
ル、ウンデシル、ドデシル等があげられる。It shows a syl ring, and the benzene ring adjacent to this ring is in the trans position. R is a hydrogen atom or a carbon atom number of 1 to 12
In the compound represented by formula (I) according to the present invention, examples of the alkyl group having 1 to 12 carbon atoms represented by R include methyl, ethyl, propyl, butyl, Examples include pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and the like.
また、上記−数式（Ｉ）で表される化合物は、４−アル
キルビフェニルカルボン酸あるいは４アルキルシクロヘ
キシル安息香酸と４″−イソプロピルフェノールとを反
応させることにより容易に製造することができる。Further, the compound represented by formula (I) above can be easily produced by reacting 4-alkylbiphenylcarboxylic acid or 4-alkylcyclohexylbenzoic acid with 4''-isopropylphenol.
かくして得られる本発明のイソプロピルフェニルエステ
ル化合物はＴＮ型液晶材料に混合することによって液晶
材料の屈折率の異方性を大きくするに有用である。The thus obtained isopropylphenyl ester compound of the present invention is useful for increasing the anisotropy of the refractive index of the liquid crystal material by mixing it with the TN type liquid crystal material.
以下、実施例によって本発明を更に詳細に説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
４−４’−７’ロピルシクロヘキシル） 自 −４
”−イソブロビルフェニルエスールのム
Ｈ１
４−（４’−プロピルシクロヘキシル）安息香Ｍ０．２
５ｇ、４−イソプロピルフェノール０．１５ｇおよびジ
シクロへキシルカルボジイミド０．２３ｇを塩化メチレ
ン１０ｄに溶解し、室温で３時間撹拌した。析出したジ
シクロヘキシル尿素をろ別した後、ろ液を脱溶媒した。Example 1 4-4'-7'ropylcyclohexyl) -4
”-Isobrobylphenyl ester M1 4-(4'-propylcyclohexyl)benzoic M0.2
5 g of 4-isopropylphenol and 0.23 g of dicyclohexylcarbodiimide were dissolved in 10 d of methylene chloride and stirred at room temperature for 3 hours. After precipitated dicyclohexyl urea was filtered off, the filtrate was desolvented.
脱溶媒残渣をｎ−ヘキサン／エチルエーテル（９／１）
を展開溶媒としてシリカゲルカラムで精製して、目的の
４− （４’−プロピルシクロヘキシル）安息香酸−４
′−（イソプロピルフェニル）エステルを得た。The solvent removed residue was dissolved in n-hexane/ethyl ether (9/1).
was purified using a silica gel column as a developing solvent to obtain the desired 4-(4'-propylcyclohexyl)benzoic acid-4.
'-(isopropylphenyl) ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
２９２０ｃ■−’ （ｓ）、 １７３０ｃｍ−’ （
ｓ）、 １６１０ｃｍ−’ （＋ａ）。2920c■-' (s), 1730cm-' (
s), 1610 cm-' (+a).
１５１０ｃｍ−’ （ｓ）、 １２７０ｃｍ−’ （
ｓ）、 １２００ｃｇｅ−’ （ｓ）、１０７５ｃ＋
ｗ−’（ｓ）
この化合物を二枚のガラス板間にはさみ、偏光顕微鏡に
よる相形態観察を行なった結果、以下の相転移を確認し
た。1510cm-' (s), 1270cm-' (
s), 1200cge-' (s), 1075c+
w-'(s) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
７７．７°Ｃ 実施例ま た。77.7°C Examples Ta.
２９２０ｃｍ−’ （ｓ）、 １７２５ｃｍ−’ （ｓ
）、 １６０５ｃｍ−’ （Ｓ）、１５０５ｃｍ＋−’
（ｓ）、 １２６０ｃｓ＋−’ （ｓ）、 １２００
ｃｍ−’ （ｓ）、１０７１０７Ｏ’ （ｓ）
この化合物を二枚のガラス板間にはさみ、偏光顕微鏡に
よる相形態観察を行なった結果、以下の相転移を確認し
た。2920cm-' (s), 1725cm-' (s
), 1605cm-' (S), 1505cm+-'
(s), 1260cs+-' (s), 1200
cm-' (s), 107107O' (s) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
イソプロビルフェニルエスールのム
Ｈ３
実１１１ｉｒ例１の４−（４″−プロピルシクロヘキシ
ル）安息香酸に代えて、４−（４’−へブチルフェニル
）安息香酸０．２７ ｇを使用した他は実施例１とまっ
たく同様の１作で、目的の４−（４’−ペンチルフェニ
ル）安息香ａＩ−４’−イソプロピルフェニルエステル
を得た。Isoprobylphenyl esul H3 Example 111ir The same procedure was carried out except that 0.27 g of 4-(4'-hebutylphenyl)benzoic acid was used in place of 4-(4''-propylcyclohexyl)benzoic acid in Example 1. The desired 4-(4'-pentylphenyl)benzoic aI-4'-isopropylphenyl ester was obtained in exactly the same manner as in Example 1.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認し参考例
本発明になる新規なイソプロピルフェニルエステル化合
物を液晶に添加することにより、液晶のΔｎを改良する
ことを見るために、次の組成になる１：１：１を混合し
た母液晶に２０％のイソプロピルフェニルエステル化合
物ヲ混合１．、て、２５°ＣにおけるそれぞれのΔｎの
変化を測定し、その結果を次に示した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and it was confirmed that it was the desired product.Reference ExampleBy adding the novel isopropylphenyl ester compound of the present invention to the liquid crystal, In order to improve the Δn of the liquid crystal, 20% isopropylphenyl ester compound was mixed into the mother liquid crystal mixed with the following composition 1:1:1. , and the changes in Δn at 25°C were measured, and the results are shown below.
上の結果から明らかなように、本発明になる新規なイソ
プロピルフェニルエステル化合物は、母液晶のΔｎの値
を大きくする効果が見られる。As is clear from the above results, the novel isopropylphenyl ester compound of the present invention has the effect of increasing the value of Δn of the mother liquid crystal.
Claims (1)
エステル化合物。 ▲数式、化学式、表等があります▼（ I ） （式中、環▲数式、化学式、表等があります▼はベンゼ
ン環またはシクロヘキシルを示し、この環と隣接するベ
ンゼン環はトランスの位置にある。Ｒは水素原子または
炭素原子数１〜１２のアルキル基を示す。）[Claims] A novel aromatic carboxylic acid ester compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, the ring ▲There are mathematical formulas, chemical formulas, tables, etc.) indicates a benzene ring or cyclohexyl, and the benzene ring adjacent to this ring is in the trans position. R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14277489A JPH0311039A (en) | 1989-06-05 | 1989-06-05 | Novel aromatic arboxylic acid ester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14277489A JPH0311039A (en) | 1989-06-05 | 1989-06-05 | Novel aromatic arboxylic acid ester compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0311039A true JPH0311039A (en) | 1991-01-18 |
Family
ID=15323278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14277489A Pending JPH0311039A (en) | 1989-06-05 | 1989-06-05 | Novel aromatic arboxylic acid ester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0311039A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5165086A (en) * | 1974-10-22 | 1976-06-05 | Merck Patent Gmbh | Bifueniruesuteruruioyobisonoseizohoho |
| JPS5785881A (en) * | 1980-11-14 | 1982-05-28 | Seiko Epson Corp | Liquid crystal composition |
| JPS59219381A (en) * | 1983-05-26 | 1984-12-10 | Sharp Corp | Liquid crystal composition |
| JPS62223292A (en) * | 1986-03-20 | 1987-10-01 | Fujitsu Ltd | Phase transition type liquid crystal composition |
-
1989
- 1989-06-05 JP JP14277489A patent/JPH0311039A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5165086A (en) * | 1974-10-22 | 1976-06-05 | Merck Patent Gmbh | Bifueniruesuteruruioyobisonoseizohoho |
| JPS5785881A (en) * | 1980-11-14 | 1982-05-28 | Seiko Epson Corp | Liquid crystal composition |
| JPS59219381A (en) * | 1983-05-26 | 1984-12-10 | Sharp Corp | Liquid crystal composition |
| JPS62223292A (en) * | 1986-03-20 | 1987-10-01 | Fujitsu Ltd | Phase transition type liquid crystal composition |
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