JPH01197459A - Optically active compound and liquid crystal composition - Google Patents
Optically active compound and liquid crystal compositionInfo
- Publication number
- JPH01197459A JPH01197459A JP2305288A JP2305288A JPH01197459A JP H01197459 A JPH01197459 A JP H01197459A JP 2305288 A JP2305288 A JP 2305288A JP 2305288 A JP2305288 A JP 2305288A JP H01197459 A JPH01197459 A JP H01197459A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- optically active
- formula
- compound
- smectic
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 239000004990 Smectic liquid crystal Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000010287 polarization Effects 0.000 abstract description 23
- 230000002269 spontaneous effect Effects 0.000 abstract description 23
- 230000004044 response Effects 0.000 abstract description 18
- -1 2-methyl-2-fluoromalonic acid ethyl-4'-hexyloxybiphenyl ester Chemical class 0.000 abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012320 chlorinating reagent Substances 0.000 abstract description 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract description 2
- RBCXEDQEZDUMHD-UHFFFAOYSA-N 2-fluoropropanedioic acid Chemical compound OC(=O)C(F)C(O)=O RBCXEDQEZDUMHD-UHFFFAOYSA-N 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000005684 electric field Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 210000002858 crystal cell Anatomy 0.000 description 5
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 4
- 230000005621 ferroelectricity Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical group OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OWFHJVJZEQPHJK-UHFFFAOYSA-N 3-ethoxy-2-fluoro-2-methyl-3-oxopropanoic acid Chemical compound CCOC(=O)C(C)(F)C(O)=O OWFHJVJZEQPHJK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101100448410 Mus musculus Gkn1 gene Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- RXNMFIKTHOCCPG-UHFFFAOYSA-N (4-octylphenyl) 4-hydroxybenzoate Chemical compound C1=CC(CCCCCCCC)=CC=C1OC(=O)C1=CC=C(O)C=C1 RXNMFIKTHOCCPG-UHFFFAOYSA-N 0.000 description 1
- IHBXBCTXNWBUJH-UHFFFAOYSA-N 1-hexoxy-4-phenylcyclohexa-2,4-dien-1-ol Chemical group CCCCCCOC1(O)CC=C(C=C1)c1ccccc1 IHBXBCTXNWBUJH-UHFFFAOYSA-N 0.000 description 1
- YIBLNPVJFPNRCQ-UHFFFAOYSA-N 1-hydroxy-4-phenylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C1=CC(C(=O)O)(O)CC=C1C1=CC=CC=C1 YIBLNPVJFPNRCQ-UHFFFAOYSA-N 0.000 description 1
- PCJLCGHQGQSHFX-UHFFFAOYSA-N 2-fluoro-2-methylpropanedioic acid Chemical compound OC(=O)C(F)(C)C(O)=O PCJLCGHQGQSHFX-UHFFFAOYSA-N 0.000 description 1
- MXOGJBKTZBIWOT-UHFFFAOYSA-N 2-phenoxycarbonylbenzoic acid Chemical group OC(=O)C1=CC=CC=C1C(=O)OC1=CC=CC=C1 MXOGJBKTZBIWOT-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical group 0.000 description 1
- YADGNRZXVLHFHB-UHFFFAOYSA-N [4-(2-methylbutoxycarbonyl)phenyl] 4-octoxybenzoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C(=O)OCC(C)CC)C=C1 YADGNRZXVLHFHB-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- AUUMFTUIVAEWQO-UHFFFAOYSA-N butane chloroform Chemical compound C(Cl)(Cl)Cl.CCCC AUUMFTUIVAEWQO-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QMSICYQQZWUMHX-UHFFFAOYSA-N diethyl 2-fluoro-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(F)C(=O)OCC QMSICYQQZWUMHX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は新規な光学活性化合物および光学活性基を有す
る液晶組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to a novel optically active compound and a liquid crystal composition having an optically active group.
「従来の技術」
液晶表示素子の表示方式として現在広く実用に供されて
いるものは、ねじれネマチック型(TN)および動°的
散乱型(DS)である。これらはネマチック型晶を主成
分としたネマチック液晶セルによる表示である。従来の
ネマチック液晶セルの短所の一つに応答速度が遅く、最
高数ミリ秒のオーダーの応答速度しか得られないとい、
う事実があげられろ。そしてこのことがネマチック液晶
セルの応用範囲をばめる一因となっている。これに対し
て最近スメクチック液晶セルを用いればより高速な応答
が得られることが明らかになってきた。"Prior Art" Currently, the display systems of liquid crystal display elements that are widely used in practical use are twisted nematic (TN) and dynamic scattering (DS). These are displays using nematic liquid crystal cells containing nematic type crystals as a main component. One of the disadvantages of conventional nematic liquid crystal cells is that their response speed is slow, with a maximum response speed on the order of several milliseconds.
Give me the facts. This is one of the factors that limits the range of applications for nematic liquid crystal cells. In contrast, it has recently become clear that a faster response can be obtained by using a smectic liquid crystal cell.
光学活性なスメクチック液晶の中には強誘電性を示すも
のであることが知られており、その応用に関して大きな
関心が持だれている。強誘電性液晶は、1975年、R
,B、メイヤー(R,B、May−er)らにより最初
に合成されたが(ジュルナール・ド・フィジーク(J
、P hys、)、36.L69(1975))、それ
は、4−(4°−n−デジルオキシベンジリデンアミノ
)−2−メチルブチルシンナメート(DOB AMB
C)を代表例とするシッフ塩基系の化合物であり、これ
が光学活性の状態、すなわちカイラルスメクチックC相
において強誘電性を示すことを特徴とするものである。It is known that some optically active smectic liquid crystals exhibit ferroelectricity, and there is great interest in their applications. Ferroelectric liquid crystal was developed in 1975 by R.
, B., May-er et al. (Journard de Physique (J.
, P hys, ), 36. L69 (1975)), which is 4-(4°-n-dedyloxybenzylideneamino)-2-methylbutylcinnamate (DOB AMB
It is a Schiff base-based compound of which C) is a typical example, and is characterized by exhibiting ferroelectricity in an optically active state, that is, in a chiral smectic C phase.
その後、N、A、クラーク(N 、A 、C1ark)
ら(アプライド・フィジクス・レターズ(A ppl、
P hys、I、 ett、)、36,899(19
80))によってDOBAMBCの薄膜セルに於て、マ
イクロ秒オーダーの高速応答性が発見され、これが契機
となって強誘電性液晶はその高速応答性やメモリ性を利
用して、液晶テレビ等のデイスプレィ用のみならず、先
プリンターヘッド、光フーリエ変換素子、ライトバルブ
等のオプトエレクトロニクス関係素子の部品にも使用可
能な材料として注目を集めている。強誘電性液晶セルに
おいては、誘電率が嵩(、自発分極が大きい材料を用い
るほどセルを高速駆動できて有利であるため、自発分極
の大きい材料の開発が望まれている。After that, N, A, Clark (N, A, C1ark)
(Applied Physics Letters (A ppl,
Phys, I, ett, ), 36,899 (19
80)) discovered high-speed response on the microsecond order in DOBAMBC thin-film cells, and this led to the development of ferroelectric liquid crystals, which utilized their high-speed response and memory properties to create displays such as LCD televisions. It is attracting attention as a material that can be used not only for industrial purposes, but also for parts of optoelectronic devices such as printer heads, optical Fourier transform elements, and light valves. In ferroelectric liquid crystal cells, it is advantageous to use a material with a large dielectric constant (and a large spontaneous polarization) because the cell can be driven at high speed, so the development of a material with a large spontaneous polarization is desired.
また実用上は、液晶組成物自身が安定であり、さらには
、室温を中心とする広い温度範囲で強誘電性を示すこと
が必要である。In addition, for practical purposes, it is necessary that the liquid crystal composition itself be stable and exhibit ferroelectricity over a wide temperature range centered around room temperature.
[発明が解決しようとする課題]
しかし、DOBAMBCなどのシッフ塩基型の化合物は
水や光等に対する安定性の点で難点があり、また強誘電
性を示す温度範囲も室温より50℃程度高温側にあるな
ど、実用に適するものではなかった。そこで、強誘電性
液晶材料として、物理的化学的に安定で、しかも大きい
自発分極を持つ材料系の実現が強く期待されている。[Problems to be solved by the invention] However, Schiff base-type compounds such as DOBAMBC have drawbacks in terms of stability against water and light, and the temperature range in which they exhibit ferroelectricity is about 50°C higher than room temperature. It was not suitable for practical use. Therefore, there are strong expectations for the realization of a material system that is physically and chemically stable and has large spontaneous polarization as a ferroelectric liquid crystal material.
本発明の課題は化学的安定性、光安定性にすぐれ、自発
分極が大きい新規な光学活性化合物および液晶組成物を
得ることにある。また本発明はこの様な新規な光学活性
化合物あるいはそれを含む液晶組成物を用いて高速応答
性を有する表示素子等を堤供しようとすることにある。An object of the present invention is to obtain a novel optically active compound and liquid crystal composition that are excellent in chemical stability and photostability and have large spontaneous polarization. Another object of the present invention is to provide a display element or the like having high-speed response using such a novel optically active compound or a liquid crystal composition containing the same.
「課題を解決するための手段」
本発明を概説すれば、本発明の第一の発明は光学活性化
合物に関する発明であって、下記一般式:
(但し、R1は炭素数1〜18のアルキル基を示し、R
2は炭素数4〜18のアルキル基、4−アルキルフェニ
ル基または 4−アルキルオキシフェニル基を示し、Q
は1または2を示し、Xは一〇−1−COO−1−OC
O−または単結合を示す)で表されることを特徴とする
。"Means for Solving the Problems" To summarize the present invention, the first invention of the present invention relates to an optically active compound, which has the following general formula: (However, R1 is an alkyl group having 1 to 18 carbon atoms. and R
2 represents an alkyl group having 4 to 18 carbon atoms, a 4-alkylphenyl group, or a 4-alkyloxyphenyl group, and Q
represents 1 or 2, X is 10-1-COO-1-OC
O- or a single bond).
また、本発明の第二の発明は液晶組成物に関する発明で
あって、エステル結合を有する光学活性なスメクチック
C液晶またはスメクチックC液晶か゛らなる成分と、前
記第一の発明の一般式(1)で表される光学活性化合物
とを含有していることを特徴とする。A second invention of the present invention relates to a liquid crystal composition, which comprises an optically active smectic C liquid crystal having an ester bond or a component consisting of a smectic C liquid crystal, and the general formula (1) of the first invention. It is characterized by containing the optically active compound represented by:
前記一般式(1)で表される化合物の中で、特に好まし
いのは、次の一般式<■>、(III)またはC’V’
)で表わされる化合物である。Among the compounds represented by the general formula (1), particularly preferred are the following general formulas <■>, (III) or C'V'
) is a compound represented by
・・・・・・(II)
(ただし、mは1〜!8、nは4〜18の整数を表す)
これらの光学活性化合物は、不斉炭素c8にフッ素およ
びカルボニル基を直接結合させているので、高い旋光性
を有している。また、中心骨格はカルボギシビフェニル
、ビフェニルカルボン酸またはカルボキシ安息香酸フェ
ニル構造を有しており、さらに分子末端に長鎖アルキル
基が存在するのでそれ自身が液晶性を示し、光学活性ス
メクチックC液晶に添加したときにその液晶性を低下さ
せることはない。......(II) (However, m represents an integer of 1 to !8, and n represents an integer of 4 to 18.) These optically active compounds have a fluorine and carbonyl group directly bonded to the asymmetric carbon c8. Therefore, it has high optical rotation. In addition, the central skeleton has a carboxybiphenyl, biphenylcarboxylic acid, or phenyl carboxybenzoate structure, and since there is a long-chain alkyl group at the end of the molecule, it itself exhibits liquid crystallinity, making it an optically active smectic C liquid crystal. When added, it does not reduce its liquid crystallinity.
一方、エステル結合を有するスメクチックC液晶性化合
物としては、特に限定されないが、例えば下記一般式(
V)あるいは(VI)で示される化合物の一種または二
種以上が使用できる。この場合、光学活性スメクチック
C液晶化合物あるいはスメクチックC液晶化合物のいず
れでも使用することができる。On the other hand, the smectic C liquid crystal compound having an ester bond is not particularly limited, but for example, the following general formula (
One or more of the compounds represented by V) or (VI) can be used. In this case, either an optically active smectic C liquid crystal compound or a smectic C liquid crystal compound can be used.
C山。+、o QcooQ C00CHIC”1l(C
I+3)CtH8・・・・・・(V)
C山C”1l(CI+、)CI+(ト3cOo○OC山
n+1・・・・・・(VI)
(ただし、式中n=4〜18の整数である)本発明にお
いて、一般式(1)、特に(II)、(■)あるいは(
tV)で示される光学活性化合物の液晶組成物全体に対
する配合量は、特に限定はされないが、例えば1〜30
重量%とすることが好ましい。C mountain. +, o QcooQ C00CHIC”1l(C
I+3)CtH8...(V) C mountain C"1l(CI+,) CI+(To3cOo○OC mountain n+1...(VI) (However, in the formula, n=an integer from 4 to 18 ) In the present invention, general formula (1), particularly (II), (■) or (
The amount of the optically active compound represented by tV) in the entire liquid crystal composition is not particularly limited, but is, for example, 1 to 30
It is preferable to set it as weight%.
光学活性化合物の配合量が上記よりも少ない場合は自発
分極の値が小さすぎて十分な応答性が得られないという
問題が生じ、光学活性化合物の配合量が上記よりも多い
場合は液晶のらせんピッチが小さくなりすぎてセル製造
が困難となるほか、カイラルスメクチックC相の温度範
囲が狭くなるという問題が生じるからである。If the amount of the optically active compound is less than the above, the problem arises that the spontaneous polarization value is too small and sufficient response cannot be obtained, and if the amount of the optically active compound is more than the above, the problem arises that the helix of the liquid crystal This is because the pitch becomes too small, which makes it difficult to manufacture the cell, and also causes the problem that the temperature range of the chiral smectic C phase becomes narrow.
本発明における光学活性化合物は、例えば次のような中
間体化合物を順次経由する方法に従って製造することが
できる。The optically active compound in the present invention can be produced, for example, according to the following method in which intermediate compounds are sequentially used.
RIOCOCF(CHs)COO11→R,0COC”
F(CH,)COO11→R,0COC”F(CI+3
)COCQ・・・・・・(り
酸成分である光学活性フルオロマロン酸モノエステルは
、ラセミ体のフルオロマロン酸ジエステルを不斉加水分
解反応して得られる。この反応の詳細については、例え
ば、光学活性−2−メチル−2−フルオロマロン酸水素
エチルの製造については、北爪らの論文(文献1:北爪
智哉ばか、日本化学会誌、1985、P212G)に記
載されており、酵素としてはセルラーゼやリパーゼ等が
用いられる。RIOCOCF(CHs)COO11→R,0COC”
F(CH,)COO11→R,0COC”F(CI+3
) COCQ (The optically active fluoromalonate monoester which is the phosphoric acid component is obtained by asymmetric hydrolysis reaction of racemic fluoromalonate diester. For details of this reaction, see, for example, The production of optically active ethyl hydrogen 2-methyl-2-fluoromalonate is described in the paper by Kitazume et al. Lipase etc. are used.
また上記の化合物のアルキル基R1の炭素数が異なる異
性体である、例えば 2−メチル−2−フルオロマロン
酸水素オクチルの製造については、まず該当の酸のジオ
クチル体を石川らの報告(石川延男ほか、ケミストリ・
レターズ、1981年、107頁)に基づいて合成し、
ついで2−メチル−2−フルオロマロン酸ジエチルと同
様にして不斉加水分解して製造できる。In addition, for the production of isomers in which the number of carbon atoms in the alkyl group R1 of the above compound differs, for example, hydrogen octyl 2-methyl-2-fluoromalonate, first the dioctyl form of the corresponding acid is prepared as reported by Ishikawa et al. (Nobuo Ishikawa). In addition, chemistry
Letters, 1981, p. 107),
It can then be produced by asymmetric hydrolysis in the same manner as diethyl 2-methyl-2-fluoromalonate.
次にこれら光学活性の酸化合物を塩化オキサリル等の塩
素化剤により酸クロライドとし、これをヒドロキシ化合
物とピリジン中で反応させて、目的とする光学活性化合
物を得ることができる。Next, these optically active acid compounds are converted into acid chlorides using a chlorinating agent such as oxalyl chloride, and this is reacted with a hydroxy compound in pyridine to obtain the desired optically active compound.
「実施例」
実施例1
光学活性−2−メチル−2−フルオロマロン酸水素エチ
ル(この化合物は!FI記の北爪らの文献!記載の方法
で製造した)2.6gを塩化メチレン中、塩化オキサリ
ル2.7mQと反応さ仕るK itazumeらの方法
(T 、K itazumeほか、ジャーナル・オブ・
オーガニック・ケミストリ(J 、Org、Chem、
)51巻、【003頁(1986年))゛により酸クロ
ライドを製造した。これをトルエン25m12に溶解し
、4−へキシルオキシ−4−ヒドロキシビフェニル4.
6gをピリジン60mQに溶解した溶液に徐々に滴下し
て、60〜.70℃で5時間反応させ、−夜装置した。"Example" Example 1 2.6 g of optically active hydrogen ethyl 2-methyl-2-fluoromalonate (this compound was produced by the method described in Kitazume et al.'s literature in FI) was chlorinated in methylene chloride. Kitazume et al.'s method of reacting with oxalyl 2.7mQ (T, Kitazume et al., Journal of
Organic Chemistry (J, Org, Chem,
), Vol. 51, p. 003 (1986)). This was dissolved in 25 ml of toluene, and 4-hexyloxy-4-hydroxybiphenyl 4.
6g was gradually added dropwise to a solution of 60mQ of pyridine to give a solution of 60~. The reaction was carried out at 70° C. for 5 hours, and the apparatus was kept overnight.
水を加えてトルエン抽出し、希水酸化ナトリウム水溶液
、及び水で洗浄し、トルエンを留去して残留物をシリカ
ゲルのカラムクロマト (溶媒へブタン−クロロホルム
)により精製し、さらに石油エーテルで再結晶して光学
活性の化合物■、すなわち2−メチル−2−フルオロマ
ロン酸エチル−4°−へキシルオキシビフェニル3.1
gを得た。Water was added and extracted with toluene, washed with dilute aqueous sodium hydroxide solution and water, the toluene was distilled off, the residue was purified by silica gel column chromatography (solvent: butane-chloroform), and then recrystallized with petroleum ether. The optically active compound (1) is ethyl-4°-hexyloxybiphenyl 2-methyl-2-fluoromalonate 3.1
I got g.
つぎにこの化合物■を厚さ約3μmの透明電極付きセル
に封入し、±5VS IHzの電界を印加しながら偏光
顕微鏡で観察すると、54.6〜58.5℃の範囲で明
瞭に応答するのが認められた。その他の相転移温度は表
1に示しである。なおSXはカイラルスメチックCある
いはそれ以外の強誘電性の状態で、上記の電界に対して
少なくとも一部が応答することを表している。SAはス
メクチックA状態、N8+iカイラルネマチツク相、■
は等方性液晶を表している。また・はその相が存在する
こと、−は存在しないことを表している。Next, this compound (■) was sealed in a cell with a transparent electrode of approximately 3 μm thickness, and when observed with a polarizing microscope while applying an electric field of ±5 VS IHz, it clearly responded in the range of 54.6 to 58.5 °C. was recognized. Other phase transition temperatures are shown in Table 1. Note that SX represents chiral smectic C or other ferroelectric state, which at least partially responds to the above electric field. SA is smectic A state, N8+i chiral nematic phase, ■
represents an isotropic liquid crystal. Also, / indicates that the phase exists, and - indicates that it does not exist.
またこの化合物を、三角波法°で自発分極を測定したと
ころ、その値は43 nC/cm”であった。Further, when the spontaneous polarization of this compound was measured using the triangular wave method, the value was 43 nC/cm''.
(以下余白)
表1
化合物R+ Q X Re Cr’l
SX SA N” 1■ Cu1ls
2 0 Cs1lts ・54.6・58
.5・64.2 − ・■ 〃2 0 CJ、、
・60.7・67.4−69.3 − −■
〃2 0 C,、l+、、 ・57.2−62
.5−66.0 − ・■ 〃2 0 C,、)l
、、 −56,0・67.4−69.2 − −
■ C,11,,20C,H,、・48.2・56.
1・62.6 − ・■ 〃2 − C,H,、・
55.3・63.8・75.4 − ・■ 〃2
Coo C,11,、・53.2・57.6・68.
5 − ・■ 〃2 Coo C?I1.s
・45.3・49.3・66.6 − ・■ 〃
2 COO−C,H,、−64,0−71,2−11
6,5−128,7−(り ” 2 Coo
−OC1+1.?−77,2・113.8・122.
2・132.5−■ 〃I COO−QC@II、
?−36.5・46.0・58.3 − −@ 〃
I Coo −Cs11+、’29.4・43.2
’55.4 *@ 〃l C0(1−0C
a11+t・27.6−42.5・56.9 − 一
実施例2
4−へキシルオキシ−4°−ヒドロキシビフェニルの代
わりにそれぞれ4−オクチルオキシ−14−デシルオキ
シ−1および4−ドデシルオキシ−4°−ヒドロキシビ
フェニルを用いる他は実施例1と同様にして光学活性化
合物■〜■を製造した。これらの化合物−の相転移温度
は表1に示した。(Left below) Table 1 Compound R+ Q X Re Cr'l
SX SA N” 1■ Cu1ls
2 0 Cs1lts ・54.6・58
.. 5.64.2 - ・■ 〃2 0 CJ,,
・60.7・67.4-69.3 - -■
〃20C,,l+,, ・57.2-62
.. 5-66.0 - ・■ 〃2 0 C,,)l
,, -56,0・67.4-69.2 - -
■ C,11,,20C,H,,・48.2・56.
1・62.6 − ・■ 〃2 − C, H,,・
55.3・63.8・75.4 −・■〃2
Coo C, 11,, 53.2, 57.6, 68.
5 - ・■〃2 Coo C? I1. s
・45.3・49.3・66.6 − ・■ 〃
2 COO-C,H,, -64,0-71,2-11
6,5-128,7-(ri ” 2 Coo
-OC1+1. ? -77,2・113.8・122.
2・132.5-■ 〃I COO-QC@II,
? -36.5・46.0・58.3 − −@ 〃
I Coo -Cs11+,'29.4・43.2
'55.4 *@ 〃l C0(1-0C
a11+t・27.6-42.5・56.9 - Example 2 4-octyloxy-14-decyloxy-1 and 4-dodecyloxy-4° instead of 4-hexyloxy-4°-hydroxybiphenyl, respectively Optically active compounds (1) to (4) were produced in the same manner as in Example 1, except that -hydroxybiphenyl was used. The phase transition temperatures of these compounds are shown in Table 1.
実施例3
2−メチル−2−フルオロマロン酸ジオクチルを用いて
前記北風らの文献!の方法により光学活性−2−メチル
−2−フルオロマロン酸水素オクチルを得た。この化合
物から実施例1と同様の方法で酸クロライドを製造した
。また4−へキシルオキシ−4°−ヒドロキシビフェニ
ルの代わりに4−オクチルオキシ−4°−ヒドロキシビ
フェニル、4−オクチル−4°−ヒドロキシビフェニル
、4−ヒドロキシ−4−ビフェニルカルボン酸オクチル
、カプリル酸−4−ヒドロキシビフェニル、4°−ヒト
aキシ−4−ビフェニルカルボン酸−4”−オフデルフ
ェニル、4−ヒドロキシ−4−ビフェニルカルボン酸−
4”−オクチルオキシフェニル、4−ヒドロキシ安息香
酸−4°−オクチルオキシフェニル、4−ヒドロキシ安
息香酸−4−オクチルフェニル、4−オクチルオキン安
息香酸−4°−ヒドロキシビフェニルを用いる以外は実
施例1と同様にして化合物■〜@を製造した。Example 3 The above-mentioned document of Kitakaze et al. using dioctyl 2-methyl-2-fluoromalonate! Optically active octyl hydrogen 2-methyl-2-fluoromalonate was obtained by the method described above. Acid chloride was produced from this compound in the same manner as in Example 1. Also, instead of 4-hexyloxy-4°-hydroxybiphenyl, 4-octyloxy-4°-hydroxybiphenyl, 4-octyl-4°-hydroxybiphenyl, octyl 4-hydroxy-4-biphenylcarboxylate, and caprylic acid-4 -Hydroxybiphenyl, 4°-human axy-4-biphenylcarboxylic acid-4''-ofdelphenyl, 4-hydroxy-4-biphenylcarboxylic acid-
Example 1 except that 4"-octyloxyphenyl, 4°-octyloxyphenyl 4-hydroxybenzoate, 4-octylphenyl 4-hydroxybenzoate, and 4°-hydroxybiphenyl 4-octyloquinebenzoate were used. Compounds ① to @ were produced in the same manner.
これらの化合物の相転移温度は表1に示しである。The phase transition temperatures of these compounds are shown in Table 1.
実施例4
化合物■と、ジエステル系液晶である光学活性−4−才
クチルオキシ安息香酸−4°−(2−メチルブチルオキ
シカルボニル)フェニル(−膜中Vにおいてn=8の化
合物)との重量比20:80の混合物を調製し、実施例
1と同様にして電界に対する応答を調べた結果、21〜
43℃の範囲で明瞭な応答を示し、また自発分極の大き
さは26 nC7cm”であった。ジエステル液晶単独
の自発分極の値は3nC/as”程度であるから、化合
物■を混合することにより、自発分極の著しい向上が達
成せきたことになる。Example 4 Weight ratio of compound (1) and optically active 4-(2-methylbutyloxycarbonyl)phenyl 4-ctyloxybenzoate (compound where n=8 in V in the film) which is a diester liquid crystal A 20:80 mixture was prepared and the response to an electric field was investigated in the same manner as in Example 1.
It showed a clear response in the range of 43°C, and the magnitude of spontaneous polarization was 26 nC/as". Since the spontaneous polarization value of diester liquid crystal alone is about 3 nC/as", by mixing compound This means that a significant improvement in spontaneous polarization has been achieved.
実施例5
化合物[相]と光学活性−4−(2−メチルブチルオキ
シカルボニル)−4−ビフェニルカルボン酸−4”−オ
クチルオキシフェニル(−膜中■においてれ=8の化合
物)との重量比10:90の混合物を調製し、実施例1
と同様にして電界に対する応答を調べた結果、74〜8
5℃の範囲で明瞭な応答を示した。Example 5 Weight ratio of the compound [phase] and optically active -4-(2-methylbutyloxycarbonyl)-4-biphenylcarboxylic acid-4''-octyloxyphenyl (-compound in the film = 8) A 10:90 mixture was prepared and Example 1
As a result of investigating the response to electric field in the same manner as 74-8
A clear response was shown in the range of 5°C.
また自発分極の大きさは18 nC/as”であった。Moreover, the magnitude of spontaneous polarization was 18 nC/as''.
このビフェニルカルボン酸エステル単独の自発分極の値
は3 nC/am’程度であるから、化合物[株]を混
合することにより、自発分極の著しい向上が達成できた
ことがわかる。Since the value of spontaneous polarization of this biphenylcarboxylic acid ester alone is about 3 nC/am', it can be seen that a significant improvement in spontaneous polarization was achieved by mixing the compound [stock].
実施例6
化合物■およびラセミ体の2−メチルブタノールから製
造したスメクチック液晶である4−才クチルオキシ安息
香酸−4°−(2−メチルブチルオキシカルボニル)フ
ェニルとの重量比10 :90の混合物を調製し、実施
例!と同様にして電界に対する応答を調べた結果、22
.5〜43℃の範囲で明瞭な応答を示し、ドメインの配
向状態も良好であった。また自発分極の大きさは21
nC/cm’であった。スメクチック液晶単独では自発
分極は存在しないので、化合物■を混合することにより
、自発分極の著しい向上が達成できたことになる。Example 6 A mixture of Compound (1) and 4°-(2-methylbutyloxycarbonyl)phenyl 4-year-old ctyloxybenzoate, a smectic liquid crystal produced from racemic 2-methylbutanol, in a weight ratio of 10:90 was prepared. And examples! As a result of investigating the response to electric field in the same manner as 22
.. A clear response was shown in the range of 5 to 43°C, and the domain orientation was also good. Also, the magnitude of spontaneous polarization is 21
nC/cm'. Since there is no spontaneous polarization in the smectic liquid crystal alone, a significant improvement in spontaneous polarization was achieved by mixing compound (1).
実施例7
化合物■、化合物[相]および、ラセミ体の2−メチル
ブタノールから製造したスメクチック液晶である4−オ
クチルオキシ安息香酸−4−(2−メチルブチルオキシ
カルボニル)フェニルとの重量比10:10:80の混
合物を調製し、実施例Iと同様にして電界に対する応答
を調べた結果、27〜67℃の範囲で明瞭な応答を示し
、それぞれを単独で使用する場合に比較して著しく広い
温度範囲で応答した。またドメインの配向状態ら良好で
あった。なお自発分極の大きさは24 nC/c+a’
であった。Example 7 Compound (1), compound [phase], and the weight ratio of 4-(2-methylbutyloxycarbonyl)phenyl 4-octyloxybenzoate, which is a smectic liquid crystal produced from racemic 2-methylbutanol, is 10: A 10:80 mixture was prepared and its response to an electric field was investigated in the same manner as in Example I. It showed a clear response in the range of 27-67°C, which was significantly broader than when each was used alone. It responded over a temperature range. In addition, the alignment state of the domains was also good. The magnitude of spontaneous polarization is 24 nC/c+a'
Met.
スメクチック液晶であるジエステル単独では自発分極は
存在しないので、化合物■および[相]を混合すること
により、自発分極の著しい向上が達成できたことになる
。Since diester, which is a smectic liquid crystal, does not exhibit spontaneous polarization alone, by mixing compound (1) and [phase], a significant improvement in spontaneous polarization was achieved.
実施例8
化合物■およびラセミ体のスメクチック液晶である4°
−(2−メチルブチルオキシカルボニル)−4=ビフェ
ニルカルボン酸−4”−オクチルオキシフェニルとの重
量比15:85 の混合物を調製し、実施例1と同様
にして電界に対する応答を調べた結果、67.5〜84
℃の範囲で明瞭な応答を示し、それぞれを単独で使用す
る場合に比較して広い温度範囲で応答した。またドメイ
ンの配向状態も良好であった。なお自発分極の大きさは
22 nC/am”であった。スメクチック液晶である
ビフェニルカルボン酸エステル単独では自発分極は存在
しないので、化合物■を混合することにより、自発分極
の著しい向上が達成できたことになる。Example 8 Compound ■ and racemic smectic liquid crystal 4°
A mixture of -(2-methylbutyloxycarbonyl)-4=biphenylcarboxylic acid and 4''-octyloxyphenyl was prepared at a weight ratio of 15:85, and the response to an electric field was investigated in the same manner as in Example 1. 67.5-84
It showed a clear response in the temperature range of °C, and responded over a wider temperature range than when each was used alone. In addition, the alignment state of the domains was also good. The magnitude of the spontaneous polarization was 22 nC/am''. Since there is no spontaneous polarization in biphenylcarboxylic acid ester alone, which is a smectic liquid crystal, a significant improvement in spontaneous polarization was achieved by mixing compound ①. It turns out.
「発明の効果」
以上説明したように、本発明によれば、次の一般式(+
)、この(T)式で表わされるものの中でも特に−膜中
(II)、(III)あるいは(1’V)で示される光
学活性化合物を用いることにより、
・・・・・・(II)
あるいはエステル結合を有するカイラルスメクチックC
液晶またはスメクチックC液晶からなる成分に前記式(
1)特に(II)、(III)あるいは(VI)で示さ
れる光学活性化合物を添加することに°より、自発分極
を増大させ、しかも力イラルスメタチッ゛りC液晶相の
温度範囲の広い液晶組成物を得ることがで、きる。"Effects of the Invention" As explained above, according to the present invention, the following general formula (+
), among those represented by formula (T), by using an optically active compound represented by (II), (III) or (1'V) in the film, ... (II) or Chiral smectic C with ester bond
The above formula (
1) A liquid crystal composition in which the spontaneous polarization is increased by adding an optically active compound particularly represented by (II), (III) or (VI), and the temperature range of the liquid crystal phase is wide. You can do it by getting .
出願人 日本電信電話株式会社
手続補正書く自発)
1、事件の表示
昭和63年特許願第23052号
2、発明の名称
(422”)日本電信電話株式会社
4、代理人
住所 東京都中央区八重洲2丁目1番5号東京駅前ビル
6階
置 (275)3921〜4番
明細書の「発明の詳細な説明」の欄
6、補正の内容
(1)明細書の第9頁第10行目に「・・・・・・(I
)」とあるのを「→(1)」と訂正する。Applicant Nippon Telegraph and Telephone Co., Ltd. Voluntary amendment to the procedure) 1. Indication of the case Patent Application No. 23052 of 1988 2. Name of the invention (422”) Nippon Telegraph and Telephone Co., Ltd. 4. Agent address 2 Yaesu, Chuo-ku, Tokyo 6th floor, Tokyo Ekimae Building, 1-5 Chome (275) 3921-4 Contents of amendments to Column 6 of "Detailed Description of the Invention" of the Specification (1) On page 9, line 10 of the specification, "・・・・・・(I
)” should be corrected to “→(1)”.
(2)明細書の第13頁の「表1」を別紙の通りに訂正
する。(2) "Table 1" on page 13 of the specification is corrected as shown in the attached sheet.
(3)明細書の第15頁第4行目に「ヒドロキシビフェ
ニル−」とあるのを「ヒドロキシフェニル」と訂正する
。(3) In the fourth line of page 15 of the specification, "hydroxybiphenyl-" is corrected to "hydroxyphenyl."
(4)明細書の第15頁下から2行目に「達成せきた」
とあるのを「達成できた」と訂正する。(4) “Achieved” on the second line from the bottom of page 15 of the specification
I corrected it to ``I was able to achieve it.''
(5)明細書の第16頁第1〜2行目および第18頁第
2行目にそれぞれ「2−メチルブチルオキシカルボニル
」とあるのをr2−メチルブチル」と訂正する。(5) "2-methylbutyloxycarbonyl" is corrected to "r2-methylbutyl" in lines 1 and 2 on page 16 and line 2 on page 18 of the specification.
(6)明細書の第16頁第17行目に「フェニル。(6) On page 16, line 17 of the specification: “Phenyl.
との重量比10 : 90の」とあるのを「フェニル(
−膜中■においてn’==8の化合物)との重量比10
:90の」と訂正する。``The weight ratio of 10:90'' is replaced by ``phenyl (
- weight ratio of compound (n'==8 in ■ in the film) to 10
:90's,” he corrected.
化合物 R3ρ X
■ Ct II s 2 0■
〃20
■ 〃20
■ 〃20
■ Cel+、、 2 0■
“ 2 −
■ 〃2COO
■ 〃20CO
@ 00C,l+、71 Co。Compound R3ρ X ■ Ct II s 2 0 ■
〃20 ■ 〃20 ■ 〃20 ■ Cel+,, 2 0■
“ 2 − ■ 〃2COO ■ 〃20CO @ 00C, l+, 71 Co.
表 !
R2Cry SX SA N” IC
,II、3 ・54.6・58.5・64.2−・C
,Il+7 ・60.7・67.4・69.3−・C
,。!(、、−57,2−62,5−66,0−C1t
llts ・56.0・67.4・69.2−・Ca
11+□ ・55,3・63.8・75.4−・C,1
1,7’ −48,2−56,1−62,6−・C,I
I、、 −53,2−57,6・68.5−C7+1
15 ・45.3・49.3・66.6−・Ca11
.7・64.0・71.2・116.5・128.7・
OC,+1.7・77.2・83.8・122.2・1
32.5・0C−1117・36.5・46.0・58
.3−・Ca11.、・29.4・43.2・55.4
−・0C811?・27.6・42.5・56,9−・
手続補正書泪鋤
ヨ
1、事件の表示
昭和63年特許願第23052号
2、発明の名称
光学活性化合物及び液晶組成物
3、補正をする者
事件との関係 特許出願人
住所 東京都中央区八重洲2丁目1番5号東京駅前ビル
6階
置(275)3921〜4番
(1) 昭和63年7月20日付提出の手続捕正書の1
6.補正6、補正の内容
(1) 「6.補正の内容」の欄の(5)に[明細書
の第16頁第1〜2行目および第18頁第2行目に」と
あるのを[明細書の第16頁第2〜3行目および第18
頁第3行目にJと訂正する。table ! R2Cry SX SA N” IC
, II, 3 ・54.6 ・58.5 ・64.2-・C
, Il+7 ・60.7・67.4・69.3−・C
,. ! (,,-57,2-62,5-66,0-C1t
llts・56.0・67.4・69.2-・Ca
11+□・55,3・63.8・75.4−・C,1
1,7'-48,2-56,1-62,6-・C,I
I, -53,2-57,6・68.5-C7+1
15 ・45.3・49.3・66.6-・Ca11
.. 7・64.0・71.2・116.5・128.7・
OC, +1.7・77.2・83.8・122.2・1
32.5・0C-1117・36.5・46.0・58
.. 3-・Ca11. ,・29.4・43.2・55.4
-・0C811?・27.6・42.5・56,9-・
Procedural amendment letter 1, Indication of the case Patent Application No. 23052 of 1988 2, Name of the invention Optically active compound and liquid crystal composition 3, Relationship to the case by the person making the amendment Patent applicant address Yaesu, Chuo-ku, Tokyo 2-1-5 Tokyo Ekimae Building 6th floor (275) 3921-4 (1) 1 of the procedure correction report submitted on July 20, 1988
6. Amendment 6, Contents of the amendment (1) In (5) of the column "6. Contents of the amendment", it is written [in the 1st to 2nd lines of page 16 and the 2nd line of page 18 of the specification]. [Page 16, lines 2-3 and 18 of the specification]
Correct J on the third line of the page.
(2)表1を別紙の通りに訂正する。(2) Correct Table 1 as shown in the attached sheet.
表 1 化合物 R,0,X R。Table 1 Compound R, 0, X R.
■ C2H520C81113 ■ 〃20 C,H,。■ C2H520C81113 ■〃〃20 C,H,.
■ 〃2ocIoH21 ■ 〃20 C,21+、。■〃2ocIoH21 ■〃〃20 C, 21+.
■ C,11,720C,+(、、。■ C, 11,720C, +(,,.
■ 〃2 Cllll17 ■ 12 COOC,11,7 ■ // 20cOC7H,。■〃〃〃〃 Cllll17 ■ 12 COOC, 11, 7 ■ // 20cOC7H,.
Claims (3)
) (但し、R_1は炭素数1〜18のアルキル基を示し、
R_2は炭素数4〜18のアルキル基、4−アルキルフ
ェニル基または4−アルキルオキシフェニル基を示し、
C^*は不斉炭素を、lは1または2を示し、Xは−O
−、−COO−、−OCO−または単結合を示す)で表
される光学活性化合物。(1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・( I
) (However, R_1 represents an alkyl group having 1 to 18 carbon atoms,
R_2 represents an alkyl group having 4 to 18 carbon atoms, a 4-alkylphenyl group or a 4-alkyloxyphenyl group,
C^* represents an asymmetric carbon, l represents 1 or 2, and X represents -O
-, -COO-, -OCO- or a single bond).
液晶化合物またはスメクチックC液晶化合物からなる成
分と、次の一般式(II)、(III)または(IV)で示さ
れる光学活性化合物とを含有することを特徴とする液晶
組成物。 ▲数式、化学式、表等があります▼・・・・・・(II) ▲数式、化学式、表等があります▼・・・・・・(III
) ▲数式、化学式、表等があります▼・・・・・・(IV) (ただし、C^*は不斉炭素を示し、mは1〜18、n
は4〜18の整数を表す)(2) Optically active smectic C with ester bond
A liquid crystal composition comprising a component consisting of a liquid crystal compound or a smectic C liquid crystal compound and an optically active compound represented by the following general formula (II), (III) or (IV). ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(III
) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(IV) (However, C^* indicates an asymmetric carbon, m is 1 to 18, n
represents an integer from 4 to 18)
クC液晶化合物またはスメクチックC液晶化合物からな
る成分が、下記一般式(V)または(VI)で示される化
合物(ただし、スメクチック液晶化合物である場合はC
^*がCを表す)である請求項2記載の液晶組成物。 ▲数式、化学式、表等があります▼・・・・・・(V) ▲数式、化学式、表等があります▼・・・・・・(VI) (ただし、式中n=4〜18の整数である)(3) If the optically active smectic C liquid crystal compound having an ester bond or the component consisting of the smectic C liquid crystal compound is a compound represented by the following general formula (V) or (VI) (however, if it is a smectic liquid crystal compound, then
3. The liquid crystal composition according to claim 2, wherein ^* represents C. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(V) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(VI) (However, in the formula, n = an integer from 4 to 18 )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2305288A JPH0751535B2 (en) | 1988-02-03 | 1988-02-03 | Optically active compound and liquid crystal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2305288A JPH0751535B2 (en) | 1988-02-03 | 1988-02-03 | Optically active compound and liquid crystal composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01197459A true JPH01197459A (en) | 1989-08-09 |
JPH0751535B2 JPH0751535B2 (en) | 1995-06-05 |
Family
ID=12099673
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2305288A Expired - Fee Related JPH0751535B2 (en) | 1988-02-03 | 1988-02-03 | Optically active compound and liquid crystal composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0751535B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02178258A (en) * | 1988-12-28 | 1990-07-11 | Showa Shell Sekiyu Kk | 2-halogen-substituted carboxylic acid derivative |
JPH03112944A (en) * | 1989-09-27 | 1991-05-14 | Nippon Mining Co Ltd | Novel fluorine-containing compound, liquid crystal composition containing same and photoswitching element |
US6096908A (en) * | 1992-01-31 | 2000-08-01 | Kashima Oil Company | Optically active fluorinated compounds |
-
1988
- 1988-02-03 JP JP2305288A patent/JPH0751535B2/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02178258A (en) * | 1988-12-28 | 1990-07-11 | Showa Shell Sekiyu Kk | 2-halogen-substituted carboxylic acid derivative |
JPH03112944A (en) * | 1989-09-27 | 1991-05-14 | Nippon Mining Co Ltd | Novel fluorine-containing compound, liquid crystal composition containing same and photoswitching element |
JP2750914B2 (en) * | 1989-09-27 | 1998-05-18 | 株式会社ジャパンエナジー | Novel fluorine-containing compound, liquid crystal composition containing the same, and optical switching element |
US6096908A (en) * | 1992-01-31 | 2000-08-01 | Kashima Oil Company | Optically active fluorinated compounds |
Also Published As
Publication number | Publication date |
---|---|
JPH0751535B2 (en) | 1995-06-05 |
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