JPH04108764A - Liquid crystal substance having optically active 1-methylnonyl group - Google Patents
Liquid crystal substance having optically active 1-methylnonyl groupInfo
- Publication number
- JPH04108764A JPH04108764A JP22254390A JP22254390A JPH04108764A JP H04108764 A JPH04108764 A JP H04108764A JP 22254390 A JP22254390 A JP 22254390A JP 22254390 A JP22254390 A JP 22254390A JP H04108764 A JPH04108764 A JP H04108764A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- phase
- antiferroelectric
- formula
- compound expressed
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 53
- 239000000126 substance Substances 0.000 title claims abstract description 7
- -1 1-methylnonyl group Chemical group 0.000 title claims description 3
- 239000000463 material Substances 0.000 claims abstract description 21
- 239000012071 phase Substances 0.000 abstract description 35
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 3
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 abstract description 2
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 abstract description 2
- 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 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 101000919340 Drosophila melanogaster Cryptochrome-1 Proteins 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- UJDJMPWYRRJDQD-UHFFFAOYSA-N decan-2-yl 4-acetyloxybenzoate Chemical compound CCCCCCCCC(C)OC(=O)C1=CC=C(OC(C)=O)C=C1 UJDJMPWYRRJDQD-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- 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〕 本発明は反強誘電相を有する新規な液晶物質に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to novel liquid crystal materials having an antiferroelectric phase.
液晶表示素子は、低電圧作動性、低消費電力性、薄型表
示が可能である事等により、現在までに、各種の小型表
示素子に利用されてきた。BACKGROUND ART Liquid crystal display elements have been used in various small-sized display elements due to their low voltage operation, low power consumption, and ability to provide thin displays.
しかし、昨今の情報、ＯＡ関連機器分野、あるいは、テ
レビ分野への液晶表示素子の応用、用途拡大に伴って、
これまでのＣＲＴ表示素子を上回る、表示容量、表示品
質を持つ高性能大型液晶表示素子の要求が、急速に高ま
ってきた。However, with the recent expansion of the application and use of liquid crystal display elements in the fields of information, OA-related equipment, and television,
Demand for high-performance, large-sized liquid crystal display elements with display capacity and display quality that exceed those of conventional CRT display elements has rapidly increased.
しかしながら、現在のネマチック液晶を使用する限りに
おいては、液晶テレビ用に採用されているアクティブマ
トリックス駆動液晶表示素子でも、製造プロ竜スの複雑
さと歩留りの低さにより、その大型化、低コスト化は容
易ではない。又、単純マトリックス駆動のＳＴＮ型液晶
表示素子にしても、大容量駆動は必ずしも容易ではなく
、応答時間にも限界がある。従って、現状においては、
ネマチック液晶表示素子は、上記の高性能大型液晶表示
素子への要求を満足するものとはいい難いのが実状であ
る。However, as long as current nematic liquid crystals are used, even active matrix drive liquid crystal display elements used for LCD TVs cannot be made larger and lower in cost due to the complexity of the manufacturing process and low yield. It's not easy. Furthermore, even with a simple matrix-driven STN type liquid crystal display element, it is not necessarily easy to drive a large capacity, and there is a limit to the response time. Therefore, at present,
The reality is that nematic liquid crystal display elements cannot be said to satisfy the above-mentioned requirements for high-performance, large-sized liquid crystal display elements.
このような状況のなかで、高速液晶表示素子として注目
されているのが、強誘電性液晶な用いた液晶表示素子で
ある。クラークとラガバールにより発表された表面安定
化型強誘電性液晶（ＳＳＦＬＣ）素子は、その従来にな
い速い応答速度と広い視野角を有する事が注目され、そ
のスイッチング特性に関しては詳細に検討されており、
種々の物性定数を最適化するため多くの強誘電性液晶が
製造されている。これとは別に、５ＳＦＬＣと異なるス
イッチング機構の素子の開発も同時に進められている。Under these circumstances, liquid crystal display elements using ferroelectric liquid crystals are attracting attention as high-speed liquid crystal display elements. The surface-stabilized ferroelectric liquid crystal (SSFLC) device announced by Clark and Ragabar has attracted attention for its unprecedentedly fast response speed and wide viewing angle, and its switching characteristics have been studied in detail. ,
Many ferroelectric liquid crystals have been manufactured to optimize various physical property constants. Separately, the development of elements with switching mechanisms different from 5SFLC is also progressing at the same time.
反強誘電相を有する液晶（以下、反強誘電性液晶と呼ぶ
）の三安定状態間のスイッチングも、これらの新しいス
イッチング機構の１つである（ Ｊ ａｐａｎｅｓｅＪ
ｏｕｒｎａｌ ｏｆ Ａｐｐｌｉｅｄ Ｐｈｙｓｉｃ
ｓ 、 Ｖｏｌ ＋２７゜ｐｐ 、Ｌ ７２９ 、１９
８８ ）。Switching between three stable states of liquid crystals with an antiferroelectric phase (hereinafter referred to as antiferroelectric liquid crystals) is also one of these new switching mechanisms (J apaneseJ
our own of Applied Physics
s, Vol +27゜pp, L 729, 19
88).
反強誘電性液晶を用いた反強誘電性液晶素子における印
加電圧と透過光量の関係を第１図に示す。この図は、直
交する偏向板間に反強誘電性液晶素子を液晶の層方向と
アナライザーまたはポラライザーが平行になるように設
置し、素子に三角波の電圧を印加し、その時の透過光の
変化を測定することンこより得らｒる。この図より、反
強誘電性液晶素子には３つの安定な挟置が存在する事が
わかる。すなわち、強誘２性液晶素子で見らｈる２つの
ユニフォーム状１（Ｕｒ。FIG. 1 shows the relationship between the applied voltage and the amount of transmitted light in an antiferroelectric liquid crystal element using antiferroelectric liquid crystal. In this figure, an antiferroelectric liquid crystal element is installed between orthogonal polarization plates so that the liquid crystal layer direction is parallel to the analyzer or polarizer, a triangular voltage is applied to the element, and the change in transmitted light is measured. Obtained from the measurement method. From this figure, it can be seen that there are three stable interpositions in the antiferroelectric liquid crystal element. That is, two uniform shapes 1 (Ur.
Ｕｌ）と第三状態である。この第三状態が反強誘電相で
あることをＣｈａｎｄａｎｉ らが報告している（Ｊ
ａｐａｎｅｓｅ Ｊｏｕｒｎａｌ ｏｆ Ａｐｐｌｉｅ
ｄ Ｐｈｙｓｉｃｓ 。Ul) and the third state. Chandani et al. reported that this third state is an antiferroelectric phase (J
apanese Journal of Applie
d Physics.
Ｖｏｌ 、２８．ｐｐ、Ｌ１２６１．１９８９． Ｊａ
ｐａｎｅｓｅ Ｊｏｕｒｎａｌｏｆ Ａｐｐｌｉｅｄ
Ｐｈｙｓｉｃｓ 、 Ｖｏｌ 、２８．ｐｐ、Ｌ１２６
５゜１９８９）。このような三安定状ｚ間のスイッチン
グが反強誘電性液晶素子の第１の特徴である。反強誘電
性液晶素子の第２の特徴は印加電圧に対して明確なしき
い値を有することである。Vol, 28. pp, L1261.1989. Ja
panese Journal of Applied
Physics, Vol. 28. pp, L126
5゜1989). Such switching between the tristable states z is the first feature of the antiferroelectric liquid crystal element. A second feature of antiferroelectric liquid crystal elements is that they have a clear threshold value for applied voltage.
第１図によって説明すると、例えば、正の電圧を徐々に
印加していった場合、透過光量はＡ−Ｂ −Ｃ−Ｄと変
化するが、透過光量は、印加電圧が０（ｖ）からＶｌ（
Ｖ） までは殆ど変化せず、印加電圧が■１α）を越
えたとき大きく変化する。次に、電圧を徐々に下げてい
った場合、透過光量はＤ −Ｅ −Ｆ−Ａと変化するが
、この場合も印加電圧がＶ２（Ｖ）になるまではｆＩＡ
−に、量は殆ど変化せず、印加電圧が■２より小さくな
った時大きく変化する。同様のことが、負の電圧を印加
した場合にもおこる。このように、反強誘電性液晶素子
は印加電圧に対し明確なしきい値を有する。更に、電圧
を上げる過程でのしきい値Ｖｌ（Ｖ） と電圧を下げ
る過程でのしきい値Ｖ２α）とが異なる事より、反強２
ｉ！電性液晶素子にはメモリー性がある事がわかる。こ
のメモリー性が反強誘電性液晶素子の第３の特徴である
。To explain with reference to FIG. 1, for example, when a positive voltage is gradually applied, the amount of transmitted light changes from A-B-C-D, but the amount of transmitted light changes from 0 (v) to Vl (
V), there is almost no change, and when the applied voltage exceeds ■1α), there is a large change. Next, when the voltage is gradually lowered, the amount of transmitted light changes to D - E - F - A, but in this case as well, until the applied voltage reaches V2 (V), fIA
-, the amount hardly changes, and changes greatly when the applied voltage becomes smaller than 2. The same thing happens when a negative voltage is applied. In this way, the antiferroelectric liquid crystal element has a clear threshold value with respect to the applied voltage. Furthermore, since the threshold value Vl (V) in the process of increasing the voltage and the threshold value V2α) in the process of decreasing the voltage are different, the anti-strong 2
i! It can be seen that electronic liquid crystal elements have memory properties. This memory property is the third characteristic of antiferroelectric liquid crystal elements.
以上のように、反強誘電性液晶を用いた素子の特徴とし
ては、三安定状態間のスイッチングを行う事、明確なし
きい値特性を有する事、良好なメモリー性を有する事等
があげられる。又、もう一つの大きな特徴として層構造
が電界により容易にスイッチングする事があげられる（
Ｊａｐａｎｅｓｅ Ｊｏｕｒｎａｌ ｏｆ Ａｐｐｌｉ
ｅｄ Ｐｈｙｓｉｃｓ。As described above, the characteristics of devices using antiferroelectric liquid crystals include switching between three stable states, having clear threshold characteristics, and having good memory properties. Another major feature is that the layered structure can be easily switched by an electric field (
Japanese Journal of Appli
ed Physics.
Ｖｏｌ 、２１Ｌｐｐ、ＬｌｌＧ、１９８９． Ｊａｐ
ａｎｅｓｅ Ｊｏｕｒｎａｌｏｆ Ａｐｐｌｉｅｄ Ｐ
ｈｙｓｉｃｓ 、Ｖｏｌ 、２９．ｐｐ、Ｌｌｌｌ。Vol, 21Lpp, LllG, 1989. Jap
anese Journal of Applied P
hysics, Vol. 29. pp, Lllll.
１９９０）。このことにより欠陥の極めて少ない液晶表
示素子の作製が可能となる。1990). This makes it possible to manufacture a liquid crystal display element with extremely few defects.
反強誘電性液晶としては、４− （１−メチルへブチロ
キシカルボニル）フェニル−４′−ｎ−オクチロキノビ
フェニル−４−カルボキシレートが知られているが、そ
の構造式及び相転移温度は以下の通りである。As an antiferroelectric liquid crystal, 4-(1-methylhebutyloxycarbonyl)phenyl-4'-n-octylquinobiphenyl-4-carboxylate is known, but its structural formula and phase transition temperature are as follows. It is as follows.
ここで、ＳＡ％ＳＣ棄、ＳＣＡ帯、ＳＩＡ豪はそれぞれ
スメクチック人相、カイラルスメクチックＣ相、反強誘
電性カイラルスメクチックＣ相、反強誘電性カイラルス
メクチックＩ相を表す。反強誘電性液晶物質としては、
特開平１−２１３３９０．特開平１−３１６３３９、特
開平１−３１６３６７、特開平１−３１６３７２、特開
平２−２８１２８の各公報及びＬｉ ｑｕｉ ｄＣｒｙ
ｓｔａｌ ｓ 、 Ｖｏｌ 、６．Ｉ）Ｉ） 、１６７
．１９８９ ｋこ記載のものが知らｈているが、文強誘
電性液晶に関する研究は始まったばかりで、現在までに
知ら九ている反強誘電性液晶物質の数は少ない。Here, SA%SC, SCA band, and SIA represent smectic physiognomy, chiral smectic C phase, antiferroelectric chiral smectic C phase, and antiferroelectric chiral smectic I phase, respectively. As an antiferroelectric liquid crystal material,
JP 1-213390. JP-A-1-316339, JP-A-1-316367, JP-A-1-316372, JP-A-2-28128 and Liqui dCry
stal s, Vol, 6. I)I), 167
．． 1989 Although the materials described above are known, research on ferroelectric liquid crystals has just begun, and the number of antiferroelectric liquid crystal materials known to date is small.
本発明の目的は、この反強誘電相を有する新規な液晶物
質を提供する点にある。液晶物質が反強誘電相を有する
か否かは、液晶物質の構造に大きく依存する。特開平１
３１６３７２号公報に開示されている化合物を例にと
ると、化合物（Ａ）は強誘電相（ＳＣ来）、および反強
誘電相（ＳＣＡ棄）を有するが、化合物（Ｂ）は強誘電
相のみを有している。このように例え、コア構造が同一
であっても、アルキル鑓部や光学活性部のわずかな炭素
数の違いにより、液晶物１が反強誘電相ををするか否か
が異なってくる。An object of the present invention is to provide a novel liquid crystal material having this antiferroelectric phase. Whether or not a liquid crystal substance has an antiferroelectric phase largely depends on the structure of the liquid crystal substance. Unexamined Japanese Patent Publication No. 1
Taking the compound disclosed in Publication No. 316372 as an example, compound (A) has a ferroelectric phase (SC) and an antiferroelectric phase (SCA), but compound (B) has only a ferroelectric phase. have. In this way, even if the core structure is the same, whether the liquid crystal material 1 exhibits an antiferroelectric phase or not depends on a slight difference in the number of carbon atoms in the alkyl base portion or the optically active portion.
また、化合物（Ａ）および（Ｂ）はいずれも強誘電相（
Ｓｅｚ）を有することより、反強誘電相の出現か強誘電
相（ＳＣ来）の出現以上に大きく液晶物質の１ｇ造に依
存していることが理解できる。Moreover, both compounds (A) and (B) have a ferroelectric phase (
It can be understood that the appearance of the antiferroelectric phase is more dependent on the 1g structure of the liquid crystal material than the appearance of the ferroelectric phase (SC).
（化合物 Ａ）
（化合物 Ｂ）
以上述べたことより明らかなように、液晶物質が反強誘
電相を有するか否かを化学構造から類推することは現状
では不可能である。個々の液晶物質の物性の測定を行っ
て初めて反強誘電相を有するか否かが明らかとなる。(Compound A) (Compound B) As is clear from the above, it is currently impossible to infer from the chemical structure whether a liquid crystal substance has an antiferroelectric phase or not. Only by measuring the physical properties of individual liquid crystal materials can it become clear whether they have an antiferroelectric phase or not.
本発明の目的は、この反強誘電…を有する新規な液晶吻
ゴを提供する点にある。An object of the present invention is to provide a novel liquid crystal display having this antiferroelectric property.
本発明は、一般式
で表される、光学活性１−メチルノニル基を含み、反強
誘電相を有する新規な液−晶物買である。ここで、ｍが
６以下および１５以上でシ１、反強誘電相を有さない。The present invention is a novel liquid crystal product represented by the general formula, containing an optically active 1-methylnonyl group and having an antiferroelectric phase. Here, when m is 6 or less and 15 or more, Si 1 does not have an antiferroelectric phase.
本発明の液晶物質の製造法の１例を反応式で示すと次の
通りである。An example of the method for producing the liquid crystal material of the present invention is shown in the following reaction formula.
ｍ Ｈｏ＄ｏｏａ ＋ ｎ−Ｃ，、Ｈ２−１Ｂｒく２〉
〔発明の効果〕
本発明は、反強誘電相を有する、新規な液晶物質を提供
するものである。そして、本発明により提供された新規
な液晶物質は、その特徴である三安定状態間のスイッチ
ング、明確なしきい値特性、良好なメモリー性を利用し
た液晶表示素子に用いる夢かできる。mHo$ooa + n-C,, H2-1Brku2> [Effects of the Invention] The present invention provides a novel liquid crystal material having an antiferroelectric phase. Further, the novel liquid crystal material provided by the present invention can be used in a liquid crystal display device utilizing its characteristics of switching between tristable states, clear threshold characteristics, and good memory properties.
り実施例〕
次に実崩例及び比較例を掲げて本発明を更に具体的に説
明するが、本発明はもちろんこれに宋定されるものでは
ない。EXAMPLES] Next, the present invention will be explained in more detail with reference to actual examples and comparative examples, but the present invention is of course not limited to these examples.
実ｌｉ＆ｉ例 １
１） ４−（４’−ｎ−オクチロキシ）と７１ニルカ
ルボン酸（１）の製造
４−（４’−ハイドロキシ）ビフェニルカルボン酸 １
０．５Ｌｎ−オクチルブロマイド １４．０ｇ、水酸化
カリウム ６．４５ｇを、エタノール １５００ゼ、水
２０〇−の混合Ｗ＆に加え、還流下で１０時間反応させ
た。更に水５００Ｍｔを加え３時間かくはんした。反応
終了後、濃塩酸を加えて酸性としてから、溶媒を５００
−留去して室温まで冷却し、白色固体を得た。これを十
分水洗してから、クロロホルムより再結晶し、目的物（
１＋を白色結晶として１２ 、 Ｑｇ得た。Example 1 1) Production of 4-(4'-n-octyloxy) and 71ylcarboxylic acid (1) 4-(4'-hydroxy)biphenylcarboxylic acid 1
14.0 g of 0.5Ln-octyl bromide and 6.45 g of potassium hydroxide were added to a mixture of 1500 g of ethanol and 200 g of water, and the mixture was reacted under reflux for 10 hours. Furthermore, 500 Mt of water was added and stirred for 3 hours. After the reaction is complete, add concentrated hydrochloric acid to make it acidic, and then reduce the solvent to 500 ml.
- Distilled and cooled to room temperature to obtain a white solid. After thoroughly washing this with water, it is recrystallized from chloroform to obtain the desired product (
12, Qg of 1+ was obtained as white crystals.
２） ４−アセトキシ−１−（１−メチルノニロキシ
ヵルボニル）ベンゼン（２１の製造４−アセトキシ安息
香酸 ３．５ｇを塩化チオニル ２５ｄに加え、還流下
で１０時間反応させた。次に、過剰の塩化チオニルを留
去してから、ピリジン １０ｍ、）ルエン５０−を加え
て、そこへ光学活性Ｓ−（＋１−２−デカノール ２．
ＯＮを滴下した。滴下後４時間加熱Ｒ施してから放冷し
、クロロホルム ５００−で希釈して、育機層を希塩酸
、ＩＮ水酸化ナトリウム水溶液、水の願で洗浄し、硫酸
マグネシウムで乾燥した。更に、溶媒を留去して粗製の
目的物（２１１，１？を得た。2) 4-acetoxy-1-(1-methylnonyloxycarbonyl)benzene (Preparation of 21) 3.5 g of 4-acetoxybenzoic acid was added to 25 d of thionyl chloride and reacted under reflux for 10 hours. After distilling off thionyl chloride, 10m of pyridine and 50m of) toluene were added, and optically active S-(+1-2-decanol 2.
ON was dripped. After dropping, the mixture was heated for 4 hours, allowed to cool, diluted with chloroform 500, and the growing layer was washed with dilute hydrochloric acid, IN aqueous sodium hydroxide solution, and water, and dried over magnesium sulfate. Furthermore, the solvent was distilled off to obtain the crude target product (211,1?).
３） ４−ハイドロキシ−１−（１−メチルノ二ロキ
シカルポニル）ベンゼン（３１の製造上記化合物（２）
の粗製物 １．８９を、エタノール ５０−に溶解させ
て、ベンジルアミン ４９を滴下した。更に室温下で４
時間攪拌したのち、クロロホルム ５ｏｏ−で希釈して
、希塩酸、水の順で洗浄し、硫酸マグネシウムで乾燥し
た。溶媒を留去してから、シリカゲルクロマトグラフィ
ーで単峻精製し、目的物（３）１．ｉを得た。3) 4-Hydroxy-1-(1-methylnonyloxycarponyl)benzene (preparation of 31 above compound (2)
1.89 of the crude product was dissolved in 50% of ethanol, and 49% of benzylamine was added dropwise. Further at room temperature 4
After stirring for an hour, the mixture was diluted with 500 ml of chloroform, washed successively with dilute hydrochloric acid and water, and dried over magnesium sulfate. After distilling off the solvent, simple purification was performed using silica gel chromatography to obtain the desired product (3) 1. I got i.
４）４−（１−メチルノニロキシヵルポニルフェニル）
−４’ ” −１クチロキシビフェニルー４−カル
ボキシレート＋４１の製造上記化合物（１）１．０．９
に、塩化チオニルエ０−を加え、１０時間加熱還流した
。過剰の塩化チオニルを留去した後、ピリジン １０ｄ
１ トルエン ６０−を加えてから、上記化合物＋３１
０．５ｇのトルエン溶液 ２０ｍを滴下し、室温で１０
時間反応させた。反応終了後、クロロホルム ５００−
で希釈シ、希塩酸、１Ｎ炭酸ナトリウム水＠液、水の順
で洗浄して、育機層を硫酸マグネシラムチ乾燥した。次
に、溶媒を留去してから、シリカゲルクロマトグラフィ
ーで単離した。次いでエタノールで再結晶して目的物（
４１０，８ｇを得た。4) 4-(1-methylnonyloxycarponylphenyl)
-4''' -1 Production of cutyloxybiphenyl-4-carboxylate +41 The above compound (1) 1.0.9
To the mixture was added 0-thionyl chloride, and the mixture was heated under reflux for 10 hours. After distilling off excess thionyl chloride, pyridine 10d
1 Add toluene 60-, then add the above compound +31
Drop 20ml of 0.5g of toluene solution and stir at room temperature for 10ml.
Allowed time to react. After the reaction is completed, chloroform 500-
The layer was diluted with water, diluted hydrochloric acid, 1N sodium carbonate solution, and then washed with water, and the growing layer was dried with magnesia sulfate. Next, the solvent was distilled off and the product was isolated by silica gel chromatography. Next, it is recrystallized with ethanol to obtain the target product (
410.8g was obtained.
目的物（４）のＩＲスペクトルを第２図に示す。The IR spectrum of the target product (4) is shown in FIG.
相の同定は、テクスチャー観察及びＤＳＣ（示差走査熱
量計）による測定により行りた。The phase was identified by texture observation and measurement using a DSC (differential scanning calorimeter).
本発明の液晶物質（４）の相系列は、次の通りであった
。The phase series of the liquid crystal material (4) of the present invention was as follows.
５）ラビング処理したポリイミド薄膜を有する。5) Has a polyimide thin film subjected to rubbing treatment.
ＩＴＯ電極電極液晶セル（セル厚 ３ｔｔｍ）に、上記
液晶物１ｉ （４１を等方相の状態で充填した。このセ
ルを、毎分１．０℃で徐冷して、ＳＡ相で液晶を配向さ
せた。セルを直交する偏向板切ニ液晶の層方向がアナラ
イザーまたはポラライザーと平行になるように設置し。An ITO electrode liquid crystal cell (cell thickness: 3 ttm) was filled with the above liquid crystal material 1i (41) in an isotropic phase.The cell was slowly cooled at 1.0°C per minute to align the liquid crystal in the SA phase. The cell was set up so that the direction of the liquid crystal layer was parallel to the analyzer or polarizer.
セルに±４０Ｖ、０，２Ｈｚ の三角波電圧を印加して
、透過光量の変化をフォトマルチプライヤ−により測定
した。その結果、１０９℃から６０℃の温度領域で、反
強誘電相に特有なダブルヒステリシスの応答履歴が認め
られた。７０℃での光学応答履歴を第３図に示す。A triangular wave voltage of ±40 V and 0.2 Hz was applied to the cell, and changes in the amount of transmitted light were measured using a photomultiplier. As a result, a double hysteresis response history characteristic of the antiferroelectric phase was observed in the temperature range from 109°C to 60°C. FIG. 3 shows the optical response history at 70°C.
実施例 ２〜７
実施例１と全く同様にして
においてｍが７．９．１０．１１．１２．１４である液
晶物質を製造し相の同定をテクスチャー観察及びＤＳＣ
による測定により行った。Examples 2 to 7 Liquid crystal materials with m of 7.9.10.11.12.14 were produced in exactly the same manner as in Example 1, and the phases were identified by texture observation and DSC.
The measurement was carried out by
こＡらの液晶物質の相系列は表１に示した通りであり、
し・ずれも反強誘電相を育していた。The phase series of these liquid crystal materials is as shown in Table 1,
Both the shift and the shift developed an antiferroelectric phase.
また実施例１の５）と同様にこれらの液晶物質の光学応
答を３べたところ、いずれも反強誘電相に特有のダブル
ヒステリシスを示した。Further, when the optical responses of these liquid crystal materials were examined in the same manner as in 5) of Example 1, all three exhibited double hysteresis characteristic of the antiferroelectric phase.
比較例 １〜２ 実施例１と全く同様にして においてｍｆ）；５及び１６の液晶物質を製造した。Comparative examples 1-2 In exactly the same manner as in Example 1 mf); 5 and 16 were prepared.
相の同定をテクスチャー観察及びＤＳＣによる測定によ
り行った。その結果を表２に示した。Phases were identified by texture observation and DSC measurements. The results are shown in Table 2.
これらの液晶物質の何れも反強誘電相は有していなかっ
た。None of these liquid crystal materials had an antiferroelectric phase.
に於ける相系列Phase series in
第１図は、一般的な反強誘電相における光学応答履歴を
示す図である。第２図は、本発明の液晶物質（４）のＩ
Ｒスペクトルを示す図である。
第３図は本発明の液晶物質（４）の光学応答履歴を示す
図である。
特許出願人 三菱瓦斯化学株式会社
代 理 人 弁理士 小 堀 貞 文
第１図
６０ｈａｔ圧FIG. 1 is a diagram showing the optical response history in a general antiferroelectric phase. FIG. 2 shows the I of the liquid crystal material (4) of the present invention.
It is a figure showing an R spectrum. FIG. 3 is a diagram showing the optical response history of the liquid crystal material (4) of the present invention. Patent applicant Mitsubishi Gas Chemical Co., Ltd. Representative Patent attorney Sadafumi Kobori Figure 1 60hat pressure
Claims (1)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22254390A JP2932638B2 (en) | 1990-08-27 | 1990-08-27 | Liquid crystal substance having optically active 1-methylnonyl group |
| EP91105252A EP0450595B1 (en) | 1990-04-04 | 1991-04-03 | Liquid crystal compound and liquid crystal display device |
| DE69107646T DE69107646T2 (en) | 1990-04-04 | 1991-04-03 | Liquid crystalline compound and liquid crystal display device. |
| US07/905,193 US5374375A (en) | 1990-04-04 | 1992-06-26 | Liquid crystal compound and liquid crystal display device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22254390A JP2932638B2 (en) | 1990-08-27 | 1990-08-27 | Liquid crystal substance having optically active 1-methylnonyl group |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04108764A true JPH04108764A (en) | 1992-04-09 |
| JP2932638B2 JP2932638B2 (en) | 1999-08-09 |
Family
ID=16784095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22254390A Expired - Lifetime JP2932638B2 (en) | 1990-04-04 | 1990-08-27 | Liquid crystal substance having optically active 1-methylnonyl group |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2932638B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5609790A (en) * | 1992-02-04 | 1997-03-11 | Seiko Epson Corporation | Liquid crystal compositions |
-
1990
- 1990-08-27 JP JP22254390A patent/JP2932638B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5609790A (en) * | 1992-02-04 | 1997-03-11 | Seiko Epson Corporation | Liquid crystal compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2932638B2 (en) | 1999-08-09 |
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