JP3491914B2 - Antiferroelectric liquid crystal composition and display device - Google Patents
Antiferroelectric liquid crystal composition and display deviceInfo
- Publication number
- JP3491914B2 JP3491914B2 JP30136192A JP30136192A JP3491914B2 JP 3491914 B2 JP3491914 B2 JP 3491914B2 JP 30136192 A JP30136192 A JP 30136192A JP 30136192 A JP30136192 A JP 30136192A JP 3491914 B2 JP3491914 B2 JP 3491914B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- group
- general formula
- compound represented
- chemical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000000126 substance Substances 0.000 claims description 18
- 239000012071 phase Substances 0.000 description 12
- 239000004990 Smectic liquid crystal Substances 0.000 description 7
- 230000005684 electric field Effects 0.000 description 7
- -1 undecyloxy group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000005620 antiferroelectricity Effects 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 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 2
- 230000007547 defect Effects 0.000 description 2
- 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 2
- 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 2
- 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 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002052 molecular layer Substances 0.000 description 2
- 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 2
- 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 2
- 229920001721 polyimide Polymers 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 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 2
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 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
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005446 heptyloxy 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])O* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、液晶組成物およびそれ
を用いた表示素子に関し、詳しくは高速応答性に優れた
３つの安定な分子配列状態を有するカイラルスメクチッ
クＣA相をとる反強誘電性液晶材料に関するものであ
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal composition and a display device using the same, and more specifically to an antiferroelectric material having a chiral smectic C A phase having three stable molecular alignment states with excellent fast response. Liquid crystal material.
【０００２】[0002]
【従来の技術】反強誘電性液晶の大きな特徴は、明確な
直流しきい値電圧の存在と、３つの安定状態にそれぞれ
メモリー性があることである。このことにより、バイア
ス電圧の存在下で単純マトリックスを用いたマルチプレ
ックス駆動が可能となる。しかしながら、一般に反強誘
電性液晶素子においては、しきい値電圧が高いことによ
り、十分な応答速度を得るために大きな電圧を印加する
必要があるという問題点が指摘されてきた。この問題点
を解決する方法として、反強誘電性を示す化合物に、２
環または３環の非カイラル化合物、あるいは３環のカイ
ラル化合物を混合することにより、反強誘電性液晶単独
の駆動電圧を２０−８０％程度低下させる方法が知られ
ている（特開平3-223390号公報参照）。しかしながらこ
の組成物のチルト角が反強誘電性液晶単独で示す値に対
し、どの程度変化しているかについては何等記載されて
いない。下記一般式［Ｉ］で示される化合物は、このも
の単独で反強誘電性を示す液晶物質として知られている
ものであるが（特開平2-160748号公報参照）、駆動させ
るために必要な電圧が高いため、実用上問題となってい
る。2. Description of the Related Art The major characteristics of antiferroelectric liquid crystals are the existence of a clear DC threshold voltage and the memory properties of each of the three stable states. This enables multiplex driving using a simple matrix in the presence of a bias voltage. However, it has been pointed out that, in general, an antiferroelectric liquid crystal device has a high threshold voltage, and thus it is necessary to apply a large voltage in order to obtain a sufficient response speed. As a method for solving this problem, a compound showing antiferroelectricity is used.
A method is known in which a driving voltage of an antiferroelectric liquid crystal alone is reduced by about 20-80% by mixing a non-chiral compound having 3 or 4 rings or a chiral compound having 3 rings (JP-A-3-223390). (See the official gazette). However, there is no description about how the tilt angle of this composition changes with respect to the value exhibited by the antiferroelectric liquid crystal alone. The compound represented by the following general formula [I] is known as a liquid crystal substance exhibiting antiferroelectricity by itself (see Japanese Patent Application Laid-Open No. 2-160748), but it is necessary for driving. This is a practical problem because of the high voltage.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、従来知られ
ている反強誘電性液晶組成物にくらべ、しきい値電圧が
低く、且つ大きなチルト角を有する反強誘電性液晶組成
物、およびそれを用いた表示素子を提供することであ
る。DISCLOSURE OF THE INVENTION The present invention is an antiferroelectric liquid crystal composition having a lower threshold voltage and a larger tilt angle than the conventionally known antiferroelectric liquid crystal composition, and It is to provide a display element using the same.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、上記目的
を達成するため鋭意検討を行った結果、本発明を完成す
るに至った。すなわち、本発明は、下記一般式［Ｉ］で
示される化合物群より選ばれる少なくとも１種類の化合
物および下記一般式［ＩＩ］で示される化合物群より選
ばれる少なくとも１種類の化合物を含有、し且つ一般式
［Ｉ］で示される化合物に対する一般式［II］で示され
る化合物の重量比は０．０１−１．２の範囲であること
を特徴とする反強誘電性液晶組成物、およびこれを用い
た表示素子である。The present inventors have completed the present invention as a result of intensive studies to achieve the above object. That is, the present invention contains at least one compound selected from the compound group represented by the following general formula [I] and at least one compound selected from the compound group represented by the following general formula [II], and General formula
A compound represented by the general formula [II] for a compound represented by [I]
The antiferroelectric liquid crystal composition is characterized by having a weight ratio of the compound of 0.01 to 1.2 , and a display device using the same.
【０００５】[0005]
【化５】 [Chemical 5]
【０００６】[0006]
【化６】 [Chemical 6]
【０００７】［発明の具体的説明］
１．液晶組成物
上記一般式［Ｉ］および［II］において、Ｒ1，Ｒ3の炭
素数６から１４のアルキル基としては、ヘキシル基、ヘ
プチル基、オクチル基、ノニル基、デシル基、ウンデシ
ル基、ドデシル基、トリデシル基、テトラデシル基等の
直鎖状、または分岐状のアルキル基が、アルコキシ基と
しては、ヘキシルオキシ基、ヘプチルオキシ基、オクチ
ルオキシ基、ノニルオキシ基、デシルオキシ基、ウンデ
シルオキシ基、ドデシルオキシ基、トリデシルオキシ
基、テトラデシルオキシ基等の直鎖状、または分岐状の
アルコキシ基が例示できる。また上記一般式［Ｉ］にお
いてＲ2の炭素数４から１２のアルキル基としては、ブ
チル基、ペンチル基、ヘキシル基、ヘプチル基、オクチ
ル基、ノニル基、デシル基、ウンデシル基、ドデシル基
等の直鎖状、または分岐状のアルキル基が、アルコキシ
アルキル基としては、メトキシブチル基、エトキシペン
チル基、メトキシヘキシル基が例示できる。[Detailed Description of the Invention] 1. Liquid Crystal Composition In the above general formulas [I] and [II], the alkyl group of R 1 and R 3 having 6 to 14 carbon atoms includes hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, Dodecyl group, tridecyl group, linear or branched alkyl group such as tetradecyl group, as the alkoxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, Examples thereof include linear or branched alkoxy groups such as dodecyloxy group, tridecyloxy group and tetradecyloxy group. In the general formula [I], the alkyl group having 4 to 12 carbon atoms represented by R 2 includes butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group and the like. Examples of the linear or branched alkyl group and the alkoxyalkyl group include a methoxybutyl group, an ethoxypentyl group, and a methoxyhexyl group.
【０００８】一般式［Ｉ］で示される化合物は、例えば
特開平2-160748号公報に記載の方法で、また一般式［I
I］で示される化合物は特願平3-336780号明細書に記載
の方法で合成することができる。The compound represented by the general formula [I] can be prepared by the method described in, for example, Japanese Patent Application Laid-Open No. 2-160748.
The compound [I] can be synthesized by the method described in Japanese Patent Application No. 3-336780.
【０００９】本発明の組成物構成する代表的化合物を例
示すれば下記のとおりである。
（１）一般式［I］で示される化合物：Typical compounds constituting the composition of the present invention are shown below. (1) Compound represented by general formula [I]:
【００１０】[0010]
【表１】 [Table 1]
【００１１】[0011]
【表２】 [Table 2]
【００１２】[0012]
【表３】 [Table 3]
【００１３】[0013]
【表４】 [Table 4]
【００１４】[0014]
【表５】 [Table 5]
【００１５】[0015]
【表６】 [Table 6]
【００１６】[0016]
【表７】 [Table 7]
【００１７】[0017]
【表８】 [Table 8]
【００１８】[0018]
【表９】 [Table 9]
【００１９】[0019]
【表１０】 [Table 10]
【００２０】[0020]
【表１１】 [Table 11]
【００２１】[0021]
【表１２】 [Table 12]
【００２２】[0022]
【表１３】 [Table 13]
【００２３】[0023]
【表１４】 [Table 14]
【００２４】[0024]
【表１５】 [Table 15]
【００２５】[0025]
【表１６】 [Table 16]
【００２６】[0026]
【表１７】 [Table 17]
【００２７】（２）一般式［II］で示される化合物：(2) Compound represented by the general formula [II]:
【表１８】 [Table 18]
【００２８】[0028]
【表１９】 [Table 19]
【００２９】[0029]
【表２０】 [Table 20]
【００３０】[0030]
【表２１】 [Table 21]
【００３１】[0031]
【００３２】[0032]
【００３３】[0033]
【００３４】[0034]
【００３５】[0035]
【００３６】[0036]
【００３７】[0037]
【００３８】[0038]
【００３９】[0039]
【００４０】[0040]
【００４１】[0041]
【００４２】[0042]
【００４３】[0043]
【００４４】[0044]
【００４５】[0045]
【００４６】[0046]
【００４７】両化合物の混合比は、一般式［Ｉ］で示さ
れる化合物に対する一般式［II］で示される化合物の重
量比で、０.０１−１.２の範囲で実施することができ
る。一般式［Ｉ］で示される化合物において、Ｒ2がア
ルキル基およびアルコキシアルキル基であって、ｍが偶
数の場合には、前記重量比が０.０１−１.２、好ましく
は０.１−１.０の範囲で実施することができる。またＲ
2がアルコキシアルキル基であって、ｍが奇数の場合に
は前記重量比が０.０１−０.２、好ましくは０.０３−
０.１５で実施することができる。The mixing ratio of both compounds is a weight ratio of the compound represented by the general formula [II] to the compound represented by the general formula [I], and it can be carried out in the range of 0.01 to 1.2. In the compound represented by the general formula [I], when R 2 is an alkyl group or an alkoxyalkyl group and m is an even number, the weight ratio is 0.01-1.2, preferably 0.1-. It can be carried out in the range of 1.0. Also R
When 2 is an alkoxyalkyl group and m is an odd number, the weight ratio is 0.01-0.2, preferably 0.03-
It can be implemented at 0.15.
【００４８】液晶組成物の調製には、一般式［Ｉ］およ
び［II］で示される化合物以外の化合物を、適量混合す
ることもできる。これらの化合物としては、例えば特開
平3-223390号公報に記載の、２環性あるいは３環性の化
合物や強誘電性液晶相において大きな自発分極を示す
か、または誘起する光学活性化合物などが例示できる
が、これに限定されるものではない。In preparing the liquid crystal composition, compounds other than the compounds represented by the general formulas [I] and [II] can be mixed in an appropriate amount. Examples of these compounds include bicyclic or tricyclic compounds described in JP-A-3-223390, and optically active compounds that exhibit or induce large spontaneous polarization in a ferroelectric liquid crystal phase. However, the present invention is not limited to this.
【００４９】２．表示素子
反強誘電性液晶素子において、反強誘電性液晶は強誘電
性液晶が持っている２つの安定状態に加え、電界無印加
時に１つの安定状態（第３の安定状態）を持っている。
この第３の安定状態では、分子層間の自発分極は打ち消
されるために、配向膜に絶縁性の材料を用いた場合でも
誘電分極を生ずることはない。また、もう１つの大きな
特徴としては、電界印加により層構造がブックシェルフ
構造とシェブロン構造の間でスイッチングすることが知
られている。この層構造のスイッチングにより、欠陥が
少なく、また一度生じた欠陥を電界印加により自己修復
できる液晶素子の作製が可能となる。2. Display element In an antiferroelectric liquid crystal element, the antiferroelectric liquid crystal has one stable state (third stable state) when no electric field is applied, in addition to the two stable states that the ferroelectric liquid crystal has. .
In the third stable state, the spontaneous polarization between the molecular layers is canceled out, so that no dielectric polarization occurs even when an insulating material is used for the alignment film. It is also known that another major feature is that the layer structure switches between the bookshelf structure and the chevron structure when an electric field is applied. By switching the layer structure, it becomes possible to manufacture a liquid crystal element having few defects and capable of self-repairing a defect once generated by applying an electric field.
【００５０】反強誘電性液晶材料を用いた液晶表示素子
は、２枚の直交する偏光板の間に液晶セルを挟み込み、
スメクチック相における分子層の法線方向と偏光子また
は検光子の方向が一致するように設置し、電界無印加時
の第３の安定状態を暗状態とし、電界印加により他方の
安定状態に変化させ、その状態を明状態として用いるこ
とにより、明および暗の表示を行わせるものである。電
界印加により得られる安定状態での分子配列は、スメク
チック相における分子層の法線方向に対し傾いており、
両者のなす角度をチルト角と呼んでいる。明状態での透
過光量は、チルト角に依存することが知られており、上
記動作モードにおいては、チルト角が４５度のときに最
も透過光量が大きくなる。A liquid crystal display device using an antiferroelectric liquid crystal material has a liquid crystal cell sandwiched between two orthogonal polarizing plates.
It is installed so that the normal direction of the molecular layer in the smectic phase and the direction of the polarizer or the analyzer coincide with each other, and the third stable state when no electric field is applied is set to the dark state, and the other stable state is changed by applying the electric field. By using that state as a bright state, bright and dark display is performed. The molecular alignment in a stable state obtained by applying an electric field is inclined with respect to the normal direction of the molecular layer in the smectic phase,
The angle formed by the two is called the tilt angle. It is known that the amount of transmitted light in the bright state depends on the tilt angle, and in the above operation mode, the amount of transmitted light becomes the largest when the tilt angle is 45 degrees.
【００５１】本発明の表示素子の作製は、透明電極が設
けられ、表面が配向処理された２枚の透明基板をスペー
サーを挟んで貼り合わせたものに、前記液晶組成物を注
入することにより実施できる。本発明の表示素子の作製
には、従来の強誘電性液晶を用いる素子の作製技術が応
用できる。例えば、配向膜の材料としては、ポリビニル
アルコール、ポリイミド、ポリアミド、ＳｉＯ、ＳｉＯ
2などを用いることができる。また、スペーサーとして
は、シリカビーズ、アルミナビーズ、ガラスファイバ
ー、ポリマーフィルムなどを用いることができる。The display device of the present invention is manufactured by injecting the liquid crystal composition into a structure in which two transparent substrates each having a transparent electrode and having a surface subjected to an orientation treatment are bonded to each other with a spacer interposed therebetween. it can. For the fabrication of the display element of the present invention, the conventional fabrication technology of the element using the ferroelectric liquid crystal can be applied. For example, as the material of the alignment film, polyvinyl alcohol, polyimide, polyamide, SiO, SiO
2 or the like can be used. Further, as the spacer, silica beads, alumina beads, glass fibers, polymer films, etc. can be used.
【００５２】[0052]
【実施例】以下、実施例により本発明をさらに具体的に
説明する。なお、実施例中の相転移温度の測定、および
相の同定は、ＤＳＣ、ならびに実施例１で説明する素子
を作製し、その電場応答を偏光顕微鏡で観察する方法に
より実施した。また、下記の表における、相転移温度
（℃）の表示に用いた略号、Ｃｒｙは結晶相を、ＳｍＣ
A＊はカイラルスメクチックＣA相を、ＳｍＣ＊はカイラ
ルスメクチックＣ相を、ＳｍＡはスメクチックＡ相を、
Ｉｓｏは等方性液体相を表し、・印はその液晶相が存在
していることを示す。EXAMPLES The present invention will be described in more detail below with reference to examples. In addition, the measurement of the phase transition temperature and the identification of the phase in the examples were carried out by the method of producing the device described in DSC and the example 1 and observing the electric field response thereof with a polarizing microscope. Further, in the table below, Cry, which is an abbreviation used for displaying the phase transition temperature (° C.), means a crystalline phase, and SmC.
A * is the chiral smectic C A phase, SmC * is the chiral smectic C phase, SmA is the smectic A phase,
Iso represents an isotropic liquid phase, and the mark-indicates that the liquid crystal phase is present.
【００５３】［実施例１］下記式［III］および［IV］
で示される化合物を用いて、表１に示される組成比で混
合し液晶組成物を調製した。透明電極付きの２枚のガラ
ス基板に配向膜としてポリイミドをスピンコートした
後、ラビング処理を施し、それらをそれぞれのラビング
方向が平行となるように、１.７μｍのギャップで貼合
わせ、セルを組み立てた。このセルに、上記組成物を等
方性液体相にして注入し、液晶状態まで徐冷した。これ
を透過軸を直交させた偏光子と検光子とで挟み、印加電
圧が０Ｖのとき、透過光量が最小となるように偏光子に
対するセルの角度を調整した。以上の手順で作製した素
子について、２５℃における印加電圧変化に対する透過
光量変化により、完全に明状態になる電圧と、そのとき
の光軸が偏光子となす角度（チルト角）を測定した。結
果を表３に示した。[Example 1] The following formulas [III] and [IV]
A liquid crystal composition was prepared by mixing the compound represented by the formula (1) with the composition ratio shown in Table 1. After spin coating polyimide as an alignment film on two glass substrates with transparent electrodes, rubbing treatment is applied, and they are attached with a gap of 1.7 μm so that the rubbing directions are parallel to each other, and a cell is assembled. It was The above composition was poured into this cell in an isotropic liquid phase, which was then slowly cooled to a liquid crystal state. This was sandwiched between a polarizer whose transmission axes were orthogonal to each other and an analyzer, and the angle of the cell with respect to the polarizer was adjusted so that the amount of transmitted light was minimized when the applied voltage was 0V. With respect to the device manufactured by the above procedure, the voltage at which the transmitted light amount changes completely with respect to the applied voltage change at 25 ° C., and the angle (tilt angle) formed by the optical axis at that time and the polarizer were measured. The results are shown in Table 3.
【００５４】[0054]
【化７】 [Chemical 7]
【００５５】[0055]
【化８】 [Chemical 8]
【００５６】［比較例１］実施例１で用いた式［III］
で示される化合物について、実施例１と全く同様の測定
を行った。その結果を表３に示した。Comparative Example 1 Formula [III] used in Example 1
The same measurement as in Example 1 was performed on the compound represented by. The results are shown in Table 3.
【００５７】[0057]
【表３８】 [Table 38]
【００５８】［実施例２］下記式［Ｖ］、［VI］および
［VII］で示される化合物を用いた以外は、実施例１と
全く同様に組成物を作製し、測定を実施した。結果を表
４に示した。Example 2 A composition was prepared and measured in exactly the same manner as in Example 1 except that the compounds represented by the following formulas [V], [VI] and [VII] were used. The results are shown in Table 4.
【００５９】[0059]
【化９】 [Chemical 9]
【００６０】[0060]
【化１０】 [Chemical 10]
【００６１】[0061]
【化１１】 [Chemical 11]
【００６２】［比較例２］実施例２で用いた式［Ｖ］お
よび［VI］で示される化合物について、それぞれ実施例
１と全く同様の測定を行った。その結果を表４に示し
た。[Comparative Example 2] The compounds of the formulas [V] and [VI] used in Example 2 were measured in exactly the same manner as in Example 1. The results are shown in Table 4.
【００６３】[0063]
【表３９】 [Table 39]
【００６４】［実施例３］実施例２において式［VII］
で示される化合物を用いる代わりに、式［IV］で示され
る化合物を用いた以外は実施例１と全く同様に組成物を
作製し、測定を実施した。結果を表５に示した。[Example 3] The formula [VII] in Example 2 was used.
A composition was prepared and measured in exactly the same manner as in Example 1 except that the compound represented by the formula [IV] was used instead of the compound represented by. The results are shown in Table 5.
【００６５】[0065]
【表４０】 [Table 40]
【００６６】［実施例４］式［VIII］および式［IX］で
示される化合物を用いた以外は実施例１と全く同様に組
成物を作製し、測定を実施した。結果を表６に示した。[Example 4] A composition was prepared and measured in exactly the same manner as in Example 1 except that the compounds represented by the formulas [VIII] and [IX] were used. The results are shown in Table 6.
【００６７】[0067]
【化１２】 [Chemical 12]
【００６８】[0068]
【化１３】 [Chemical 13]
【００６９】［比較例３］実施例４で用いた式［VIII］
で示される化合物について、実施例１と全く同様の測定
を行った。その結果を表６に示した。Comparative Example 3 Formula [VIII] used in Example 4
The same measurement as in Example 1 was performed on the compound represented by. The results are shown in Table 6.
【００７０】[0070]
【表４１】 [Table 41]
【００７１】［実施例５］式［Ｘ］、式［XI］および式
［IV］で示される化合物を用いた以外は実施例１と全く
同様に組成物を作製し、測定を実施した。結果を表７に
示した。Example 5 A composition was prepared and measured in exactly the same manner as in Example 1 except that the compounds represented by formula [X], formula [XI] and formula [IV] were used. The results are shown in Table 7.
【００７２】[0072]
【化１４】 [Chemical 14]
【００７３】[0073]
【化１５】 [Chemical 15]
【００７４】［比較例４］実施例５で用いた式［IV］で
示される化合物の代わりに式［XII］で示される化合物
を用いた以外は、実施例５と全く同様にして組成物を作
製し測定を行った。その結果を表７に示した。一般式
［II］で示される化合物以外の強誘電性液晶化合物を用
いた場合には組成物のチルト角が小さくなった。[Comparative Example 4] A composition was prepared in the same manner as in Example 5 except that the compound represented by the formula [XII] was used instead of the compound represented by the formula [IV] used in Example 5. It was produced and measured. The results are shown in Table 7. When a ferroelectric liquid crystal compound other than the compound represented by the general formula [II] was used, the tilt angle of the composition was small.
【００７５】[0075]
【化１６】 [Chemical 16]
【００７６】［比較例５］実施例５で用いた式［IV］で
示される化合物の代わりに式［XIII］で示される化合物
を用いた以外は、実施例５と全く同様にして組成物を作
製し測定を行った。その結果を表７に示した。一般式
［II］で示される化合物以外の２環性スメクチック液晶
化合物を用いた場合には組成物のチルト角が小さくなっ
た。Comparative Example 5 A composition was prepared in the same manner as in Example 5 except that the compound represented by the formula [IV] used in Example 5 was replaced by the compound represented by the formula [XIII]. It was produced and measured. The results are shown in Table 7. When a bicyclic smectic liquid crystal compound other than the compound represented by the general formula [II] was used, the tilt angle of the composition was small.
【００７７】[0077]
【化１７】 [Chemical 17]
【００７８】[0078]
【表４２】 [Table 42]
【００７９】[0079]
【発明の効果】本発明の一般式［Ｉ］および［II］で示
される化合物を混合することにより駆動電圧が低く、か
つ一般式［Ｉ］で示される化合物が有するチルト角をほ
とんど低下させることのない反強誘電性液晶組成物を得
ることができる。INDUSTRIAL APPLICABILITY By mixing the compounds represented by the general formulas [I] and [II] of the present invention, the driving voltage is low and the tilt angle possessed by the compound represented by the general formula [I] is almost reduced. It is possible to obtain an antiferroelectric liquid crystal composition free from the above.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ０９Ｋ 19/34 Ｃ０９Ｋ 19/34 Ｇ０２Ｆ 1/13 ５００ Ｇ０２Ｆ 1/13 ５００ Ｇ０９Ｆ 9/35 Ｇ０９Ｆ 9/35 (56)参考文献 特開 平２−160748（ＪＰ，Ａ) 特開 平４−198155（ＪＰ，Ａ) 特開 平３−223390（ＪＰ，Ａ) 特開 平３−106850（ＪＰ，Ａ) 特開 平５−65486（ＪＰ，Ａ) 特開 平５−201929（ＪＰ，Ａ) 特開 平５−163208（ＪＰ，Ａ) 特開 平５−186402（ＪＰ，Ａ) 特開 平３−11041（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 69/90 - 69/94 C07D 239/26 C07D 239/34 C09K 19/20 C09K 19/34 ＣＡ（ＳＴＮ) ＣＡＯＬＤ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 7 Identification code FI C09K 19/34 C09K 19/34 G02F 1/13 500 G02F 1/13 500 G09F 9/35 G09F 9/35 (56) References Kaihei 2-160748 (JP, A) JP 4-198155 (JP, A) JP 3-223390 (JP, A) JP 3-106850 (JP, A) JP 5-65486 ( JP, A) JP 5-201929 (JP, A) JP 5-163208 (JP, A) JP 5-186402 (JP, A) JP 3-11041 (JP, A) (58 ) Fields surveyed (Int.Cl. 7 , DB name) C07C 69/90-69/94 C07D 239/26 C07D 239/34 C09K 19/20 C09K 19/34 CA (STN) CAOLD (STN) REGISTRY (STN)
Claims (2)
り選ばれる少なくとも１種類の化合物、および下記一般
式［ＩＩ］で示される化合物群より選ばれる少なくとも
１種類の化合物を含有することを特徴とする反強誘電性
液晶組成物。 【化１】 【化２】 ここで、一般式［Ｉ］で示される化合物に対する一般式
［ＩＩ］で示される化合物の重量比は０．０１−１．２
の範囲である。1. Containing at least one compound selected from the group of compounds represented by the following general formula [I] and at least one compound selected from the group of compounds represented by the following general formula [II]. A characteristic antiferroelectric liquid crystal composition. [Chemical 1] [Chemical 2] Here, the general formula for the compound represented by the general formula [I]
The weight ratio of the compound represented by [II] is 0.01-1.2.
Is the range .
を用いた表示素子。 【化３】 【化４】 ここで、一般式［Ｉ］で示される化合物に対する一般式
［ＩＩ］で示される化合物の重量比は０．０１−１．２
の範囲である。2. A display device using the antiferroelectric liquid crystal composition according to claim 1. [Chemical 3] [Chemical 4] Here, the general formula for the compound represented by the general formula [I]
The weight ratio of the compound represented by [II] is 0.01-1.2.
Is the range .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30136192A JP3491914B2 (en) | 1992-11-11 | 1992-11-11 | Antiferroelectric liquid crystal composition and display device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30136192A JP3491914B2 (en) | 1992-11-11 | 1992-11-11 | Antiferroelectric liquid crystal composition and display device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06145111A JPH06145111A (en) | 1994-05-24 |
| JP3491914B2 true JP3491914B2 (en) | 2004-02-03 |
Family
ID=17895948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30136192A Expired - Lifetime JP3491914B2 (en) | 1992-11-11 | 1992-11-11 | Antiferroelectric liquid crystal composition and display device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3491914B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05302085A (en) * | 1992-04-27 | 1993-11-16 | Mitsubishi Gas Chem Co Inc | Pyrimidine-based liquid crystal substance |
| EP0737733B1 (en) * | 1995-04-14 | 2001-02-21 | Mitsubishi Gas Chemical Company, Inc. | Liquid crystal compound having ferrielectric phase and liquid crystal composition |
-
1992
- 1992-11-11 JP JP30136192A patent/JP3491914B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06145111A (en) | 1994-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2937274B2 (en) | Antiferroelectric liquid crystal composition | |
| EP0694599B1 (en) | Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method | |
| EP0637622B1 (en) | Liquid crystal device | |
| EP0467662A2 (en) | Liquid crystal racemic mixture, liquid crystal composition and liquid crystal element, process for manufacturing and uses thereof | |
| JP3406014B2 (en) | Antiferroelectric liquid crystal composition and display device | |
| JP3491914B2 (en) | Antiferroelectric liquid crystal composition and display device | |
| EP0677565B1 (en) | Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method | |
| KR100354351B1 (en) | Liquid crystal compositions and liquid crystal elements containing them | |
| JPS63172788A (en) | Liquid crystal composition and liquid crystal element containing the same | |
| EP0636673A2 (en) | Liquid crystal mixture and liquid crystal element comprising the same | |
| JPH0243283A (en) | Ferroelectric liquid crystal composition | |
| JP2953624B2 (en) | Ferroelectric liquid crystal composition | |
| JPH0639586B2 (en) | Liquid crystal composition | |
| JP3383015B2 (en) | Liquid crystal optical element | |
| JPH03259992A (en) | Ferroelectic liquid crystal composition and ferroelectic liquid crystal element | |
| JPH1088139A (en) | Liquid crystal element and its production | |
| JP3111610B2 (en) | Ferroelectric liquid crystal composition and device | |
| JPH086029A (en) | Liquid crystal optical element | |
| KR19990072773A (en) | Ferrielectric liquid crystal compound | |
| JPH08151579A (en) | Liquid crystal composition and liquid crystal element containing the same | |
| JPH09176650A (en) | Antiferroelectric liquid crystal composition | |
| JPH09176133A (en) | Ether group-bearing phenylpyrimidine compound, liquid crystal material, liquid crystal composition and liquid crystal element | |
| JPH06200252A (en) | Liquid crystal composition and liquid crystal element containing the same | |
| JPS63101481A (en) | Liquid crystal composition and liquid crystal element obtained by using same | |
| JPH0559366A (en) | Ferroelectric liquid crystal composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081114 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081114 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091114 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101114 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111114 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121114 Year of fee payment: 9 |
|
| EXPY | Cancellation because of completion of term |