JPS58136680A - Nematic liquid crystal composition - Google Patents
Nematic liquid crystal compositionInfo
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- JPS58136680A JPS58136680A JP1712482A JP1712482A JPS58136680A JP S58136680 A JPS58136680 A JP S58136680A JP 1712482 A JP1712482 A JP 1712482A JP 1712482 A JP1712482 A JP 1712482A JP S58136680 A JPS58136680 A JP S58136680A
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- liquid crystal
- nematic liquid
- formula
- voltage
- nematic
- Prior art date
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- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
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- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
Description
【発明の詳細な説明】
本１ｕｉａネマチック箪晶組威物に係）、勢に？Ｎ（ね
じれ″ネマチック）ｍ表示装置中ネガ表示タイグＯゲス
トホスト蓋表示装置に適し九正Ｏ霞電異方法を有するネ
マチック液晶組成物に関する。 ゛
ＴＮＩＩＩＩ示俟置は消費装力が極めて少表く、かつ受
光ｉｇｉ＊示である丸め見易く疲れないなどＯｌｋの表
示装置にないすぐれた特徴を有してい。[Detailed Description of the Invention] This book relates to the nematic nematic crystal kimono), in force? N (twisted nematic) Nematic liquid crystal composition suitable for negative display type guest host lid display device in N (twisted nematic) display device. It also has excellent features not found in Olk's display devices, such as a round light receiving igi* display that is easy to view and not tiring.
るえめ腕時計や電卓などの製品に広く使用されて−る。It is widely used in products such as watches and calculators.
ヒれらはいずれも水銀電池勢の小皺電源を用いているの
で、長期にわ尋る使用をはかる友めには、皺表示装置０
ｆＩ４費電力をなるべく少なくする友めに駆動電圧を低
下するくとが望。All fins use a mercury battery-based wrinkle power source, so if you plan on using it for a long time, please use the wrinkle display device 0.
It is desirable to lower the drive voltage to reduce fI4 power consumption as much as possible.
まれる。さらに設鼾上の観点からも、駆動電圧が・１．
るＶ以下、すなわち電池１ケでダイナンツク厘動ができ
るような該表示装置が要望されている。
・
一方正の誘電異方性を有するネマチック液晶にカイ。′
：）ル物質を添、加してカイツルネマチック液晶とし、
それに色素を添加したものは、電圧を印加することによ
）カイツルネマチック液晶（コレスデリック液晶）から
ネマチック液晶に相転移するととＫよりカラー表示が出
来るゲストホストｌ１ｉＩＫ晶表示装置に使用すること
、が出来、このタイプの表示装置紘逼光板を使用せずＫ
あざやかなカッ−表示が可、能であることから最近注目
をあびている。しかしカイラル物質を添加すｈえめＫＨ
Ｉ―電圧が轟くな９実用上の大きな一書とをって％／＆
る。be caught. Furthermore, from the point of view of snoring installation, the driving voltage is 1.
There is a demand for a display device that can be operated dynamically with less than V, that is, with just one battery.
・On the other hand, nematic liquid crystals have positive dielectric anisotropy. ′
:) Adding and adding substances to make a nematic liquid crystal,
When a dye is added to it, it undergoes a phase transition from a nematic liquid crystal (cholesderic liquid crystal) to a nematic liquid crystal by applying a voltage, and is used in a guest host l1iIK crystal display device that can display colors from K. This type of display device can be used without using a light-transmitting plate.
It has recently been attracting attention because it is capable of displaying vivid images. However, if chiral substances are added,
I-Don't let the voltage roar 9 A big practical book %/&
Ru.
従来しき一億電圧の低い液晶化合物としてはｐ−シアノ
フェニル−ｐ′−アルキルベンゾエート、ｐ−シアノフ
エ品ルチオールーｐ′−アルキルベンゾエート、暴−シ
アノ−！−（４−アルキル７エエル）−ビリさヂンなど
のよう１ｋｌＩ電異：ＩＦ性Ｏ大１１１ｋｉＩｌｌ！晶
材料が知られてお〕、又、それ一体紘液晶で＃ｉ１に％
／％が２−シアノ−４−（４’−聴一アルキルフェニル
）７ラン、！−シア／−＠−（４−１−アルキルフェニ
ル）チオフェンなどのシアノ化金物をネマチック液晶材
料Ｋ１１ｍ１するととによって、しきい値電圧を低下さ
せることが可能なことは知られていた。しかしこれらの
物質をｊＩ−九だけで所望のしきい値電圧を有するネｉ
チック材料を構成した揚台に妹、低温Ｋｍ％／Ｔｈて結
晶が析出したヤ、詰腹が１
着しく増大し応答性を着しく遅らせるという岡厘点かあ
りえ。このような状況に鑑みて本発明者ら社、正の誘電
異方性を有するネマチック液晶材料を用いる表示装置に
おけるしきい値電圧の低下策をもとめて、種々検討しえ
結果本発―に到達し良。Conventional liquid crystal compounds with a low voltage of 100 million are p-cyanophenyl-p'-alkyl benzoate, p-cyanophenyl ruthiol-p'-alkyl benzoate, and cyclo-cyano! -(4-Alkyl 7EL) - 1klI electric difference like biridadin etc.: IF sex O large 111kiIll! The crystal material is known], and it is also the same as #i1% in Hiro liquid crystal.
/% is 2-cyano-4-(4'-alkylphenyl) 7 runs,! It has been known that the threshold voltage can be lowered by adding a cyanated metal such as -thia/-@-(4-1-alkylphenyl)thiophene to the nematic liquid crystal material K11m1. However, these materials can be combined with a neutral having the desired threshold voltage with only jI-9.
It is possible that crystals precipitate on the platform made of the tic material at low temperatures (Km%/Th), which increases the amount of filling and slows down the response. In view of this situation, the inventors of the present invention sought a method for lowering the threshold voltage in a display device using a nematic liquid crystal material having positive dielectric anisotropy, and after conducting various studies, they arrived at the present invention. Good.
即ち、本発明は一般式
（上式中、ａＦｉ＠〜２４であり、ｍ ＦｉＯ又はｌで
ある）
で表わされるｂ−置換−１，８−ジオキサ−２−オンの
少くとも１種を１−ｉｏ重量％含有してなるネ！チック
液晶組成物である。本発明においては一般式（１）で示
される１、３−ジオキサ−２−オンの６−置換体の少な
くとも１種が使用され、その量は液晶組成物の１−８０
重量％０ｆｌｉ’ｌ！ＩＫ配合するのが適轟で゛ある。That is, the present invention provides at least one b-substituted-1,8-diox-2-one represented by the general formula (in the above formula, aFi@~24 and m FiO or l) as a 1- Contains io weight%! It is a liquid crystal composition. In the present invention, at least one type of 6-substituted 1,3-diox-2-one represented by general formula (1) is used, and the amount thereof is 1-80% of the liquid crystal composition.
Weight%0fli'l! It is appropriate to mix IK.
１重量％以下の配合で社動作電圧の低下効果が少なく、
又１０００食％以上の配合は該化合物が液晶相を示さな
いので表示セルの動作可能な温度範囲の上隈を低下させ
る。With a content of 1% by weight or less, there is little effect of lowering the operating voltage.
In addition, if the compound is added in an amount of 1000% or more, the compound does not exhibit a liquid crystal phase, which lowers the upper temperature range in which the display cell can operate.
本発ｆＩＡにおいて用いるネマチック液晶化合物虞は龜
威物紘４１に一定されるものでないが、七〇最もよく使
用される代表的なものをあげれば翼ＸΣＣＮ （Ｒはア
ルキル基またはアルコキシ基、以下間＝’＞で代表され
るシアノビフェール系筐晶、Ｒ÷＜ＣＮで代表される
ＰＣＢ系筐晶液晶（ンＣ００ＧＣＮで代表れヂン系筐畠
などの正の誘電異方性を膚する液晶物質及びそれらを含
む液晶組成物、そして多くＯ鳩舎これら正ＯＩＩ電異方
性を有する液晶と混合して用いられるＲ−４ΣＣＯω（
）橿ｒ代貴され！ＥＣＭ系筐晶、液晶ｃｏｏＱｇ’で代
表されるエステル系液晶、Ｒ÷仝ＧＲ’で代表されるＮ
−ＰＣＨ系箪晶液晶の負（又はＯ付近Ｏ値）の霞電異方
性管有する液晶物質及びそれらを含む諌晶ｍ＊物である
。The nematic liquid crystal compounds used in the fIA of the present invention are not limited to 41, but the most commonly used representative ones are 70. Liquid crystal materials exhibiting positive dielectric anisotropy, such as cyanobifer-based crystals represented by ＝'＞, PCB-based liquid crystals represented by R÷＜CN (represented by C00GCN), etc. and liquid crystal compositions containing them, and many R-4ΣCOω (
) It's been a long time since I've been able to do it! ECM-based case crystal, ester-based liquid crystal represented by cooQg', N represented by R÷GR'
These are liquid crystal substances having a negative (or O value near O) haze-electric anisotropy of -PCH-based diagonal liquid crystals, and meridian m* substances containing them.
次に本発ｍＫｌｋて使用するＳ７置換−１，８−ジオキ
サ−２−オンの製法について述べる。Next, a method for producing S7-substituted-1,8-diox-2-one used in the mKlk of the present invention will be described.
まず（１）式で示される化金物のうちｍ −０＊ ｎ
−００化合物、即ちプロパン−１，８−ｔイクリツクカ
ーボネートは既知物質であ？て（Ｌ−Ｈｏｕｇｈら＊
Ｊ−ｃｈ＠ｍ−５ｏｃ−、１９１ｉＬ ｐ６８１−４）
、少量の金属ナトリウムを入れた３−プロパンジオール
と炭酸ジエチルを加熱反応させる仁とＫより得す−２−
オン類及びｂ−アリール−１，８−ジオキサ−冨−オン
類社同様にして２−アルキル−１，８−プロパンジオー
ル又Ｆｉｔ−ｐ−アルキルフェニル−１，８−７’ロバ
ンジオ一ルト脚駿ジエチルを触媒量のナトリウムエトキ
シド又は金属ナトリウムと共に加熱し、生成するエタノ
ール及び過剰の炭酸ジエチルを留去してからアルカリ存
在下減圧蒸留することによって得られる。First, among the metal compounds represented by formula (1), m −0* n
Is the -00 compound, propane-1,8-t electric carbonate, a known substance? (L-Hough et al. *
J-ch@m-5oc-, 191iL p681-4)
, obtained from Jin and K by heating and reacting 3-propanediol and diethyl carbonate containing a small amount of metallic sodium-2-
2-alkyl-1,8-propanediol or Fit-p-alkylphenyl-1,8-7' lovandiolutocarcinol It is obtained by heating diethyl together with a catalytic amount of sodium ethoxide or metallic sodium, distilling off the produced ethanol and excess diethyl carbonate, and then distilling it under reduced pressure in the presence of an alkali.
これらＯ化合物の代表的なものの物性を示すと− １，１１−ジオキｔ−１−オン（グロパンーｌ。The physical properties of typical O compounds are shown below. 1,11-dioquit-1-one (glopan-l.
Ｓ−ｔイタリックカーｌネーＦ） 鳳、ＩＰ０番８℃。S-t italic carne F) Otori, IP number 0 8℃.
Ｓ−エテに−１，Ｓ−ジオ命デー３−オン１１１．１０
６〜ｌＯ’Ｆ℃／寓ｍ１１ｇ。S-Ete ni-1, S-Geo life day 3-on 111.10
6-10'F°C/11g.
６−プーピＪｌｙ−１ｅ ３−ジオ命ナー８−オンｂ、
１．１１５〜１１８℃７１１１１１１９゜６−プテルー
１．３−ジオ中ナー２−オンｂ、ｐ、１８０〜１１１℃
／３■麗１゜尋−べｙｔｈ−１，３−ジオ命ナー２−オ
ン）、Ｐ、１８０〜１２１’ｃ／２−１１ 。6-Poupi Jly-1e 3-Gio Lifener 8-On b,
1.115-118℃ 71111119゜6-Pteru1.3-dione 2-one b, p, 180-111℃
/3■Rei 1゜fathom-Bayth-1,3-geo-inner 2-on), P, 180-121'c/2-11.
６−ヘキシルｔｈ１，３−ジオ命ナー２−オン）、１１
．１３５〜１３１℃／寓諷１ｇ 。6-hexyl th1,3-dione (2-one), 11
．． 135-131℃/1g.
Ｓ−へブチｅ−１．３−ジオキナー２−オン１１、ｐ、
１６３〜１６ｓ’ｃ／ｌ亀−９６−オタチルー１．５
−ジオ中ナー２−オン墓、）、９６．５〜９ツ、６℃。S-hebutye-1,3-dioquiner-2-one 11, p,
163-16s'c/l Kame-96-Otachiru 1.5
-Geochunar 2-on grave, ), 96.5-9, 6°C.
５−シープ田ビルフエエ＃−１ｅ３−ジオキナ−２−オ
ｙ鳳ｅｌｌ＋＋ ｅｓ、ｓ〜９１．６℃。5-Sheep Tabiruhue#-1e3-dioquina-2-oyhoell++es, s ~ 91.6°C.
ａ−ｐ−プチルフエエＪ”−１ｍ ３−ジオ命す−３−
オ／朧、ｐ、４Ｌ８〜４６−Ｉ Ｔ； ＃
るーｐ−ペンチルフェニル−１，１１−ジオキナ−雪−
オン
ｍｐ、＠・〜６１℃
などである。a-p-Putylhue J”-1m 3-Geo Order-3-
O/Oboro, p, 4L8~46-IT; # Lu-p-pentylphenyl-1,11-dioquina-yuki-
Onmp, @・~61°C, etc.
崗原料Ｏｔつである冨−アルキルー１．８−プロパンジ
オールはアル中ルーマーン酸ジエステルを水嵩化リチク
ムアル１＝りムで還元することによって得られ（４１ｊ
ｌｌＨｓ−ｘｓ４ｔｙｓ号弛）、又もう１）０１−アリ
ール−１，３−ブーパンジオールも８−アリール−１，
ｓ−プロパンジオール類を水素化リチクムアル電ニウム
で還元することＫよ）得られる（籍−昭６６−ｓｓｓｓ
ｓ号など）。Tomi-alkyl-1,8-propanediol, which is a raw material for aluminum, is obtained by reducing lumenic acid diester in alkali with water-enriched lyticum aluminum (41j
llHs-xs4tys), and 1) 01-aryl-1,3-butanediol is also 8-aryl-1,
By reducing s-propanediol with lyticum aluminum hydride, it can be obtained (K).
s, etc.).
以下実施例によｐ本発明の液晶組成物について更に詳細
に説明する。The liquid crystal composition of the present invention will be explained in more detail below using Examples.
実施Ｍｌ（Ｍ−ペンチルー１．８−ジオキサ−雪−オン
（（Ｉ）式で１１−５．ｍ−Ｏのもの）１１
の製造）
１− ペアｆｋ−１、ＩＩ−ジ、ｔ−＃１０Ｏｆ炭酸ジ
エチル１０ｉｉ金属ナトリウムａ、Ｓｔをｓａｙツスコ
に入れて加熱し、生成するエタノールを留去しつつ筐温
が１４・”ＯＫなる壜でｍ−した。残奮物にトルエンを
加えてから少量の水で洗浄して中性とし、トルエンを留
去後魯鱈珈Ｏ減圧下に１４１”Ｃまでの留分な除去する
。＊冑物紘粘稠であ夛オリゴマー′＆−シポリマー状で
ある。これにナト”リウム工）中シトを加えてアルカリ
性にし解重合しつつ減圧菖奮すると目的物であるＳ−ペ
ンチル−１，８−ジオキナ−鵞−オンが１１１１〜１！
！６℃／！ＩＩＩＨＩＯ奮分として得られえ。これを更
に再１１１して１１！ ０〜ｔ ！！ ！’Ｃ／ ２ｓ
ｎｕｇ ０９１分５ｓｔｔ得え、ヒＯ物ＯＮＭＢスペク
トル及び赤外線徴収スペクトルはＳ−ペンチル−１，８
−ジオ命ナー雪−オンの構造式と矛盾しなかつ良。又そ
の元素分析値は次の通勤で理論値とよ※−款している。Implementation Ml (Preparation of M-pentyl-1,8-dioxa-snow-one (11-5.m-O in formula (I)) 11) 1- Pair fk-1, II-di, t-#10Of Diethyl carbonate 10ii metal sodium a, St was heated in a sayotsco, and while the ethanol produced was distilled off, the temperature of the casing was 14. The mixture was washed with water to make it neutral, and after distilling off the toluene, the fractions up to 141"C were removed under reduced pressure. *It is viscous and has the form of oligomers and polymers. Adding sodium chloride to the mixture to make it alkaline and depolymerizing it under reduced pressure yields the target product, S-pentyl-1,8-dioquina-one, at 1111-1!
! 6℃/! IIIHIO I hope you can get it as much as you can. Repeat this again to 111 and get 11! 0~t! ! ! 'C/2s
nug 091 min 5stt obtained, arsenic ONMB spectrum and infrared collected spectrum are S-pentyl-1,8
-Consistent with the structural formula of Geo-Inner Snow-On. Also, the elemental analysis value will be determined as the theoretical value on the next commute.
分析値 通論値（Ｃ・Ｈｓ＠Ｏｉとして）ｃ ＠
ｔ・％ ＩＬ７６％
Ｈ１１Ｌｈ％ ９．ｓ＠％
実施例！（６−（ｐ−プロピルフェニル）−１゜魯−ジ
オキナ−２−オン（（１）式で慕虐畠。Analytical value General value (as C・Hs@Oi) c @
t・% IL76% H11Lh% 9. s@% Example! (6-(p-propylphenyl)-1゜lu-dioquina-2-one (formula (1)).
鵬膳ｌのもの）ＯＩＩ造）
ト直ｐ−プロピルフェニル）−１，８−ジオール（ｍ−
Ｐ−８４４〜ＩＩ！１１．７℃）Ｓｏｆ、炭酸ジエチル
６１ｆ及びナトリクムエトキシドｌｆを蒸留フラスコに
入れて加熱し、生成するエタノールを留去しりつ液温が
１４０″ＯＫなるまで加熱し、更に１００℃で３時間加
熱しえ、減圧−１１によって過刺の炭酸ジエチルを留去
し、更Ｋ Ｏ，６−］ＥＩｇｏ減圧下で解重合しながら
蒸留してす、ｐ、ｘｓｏ−１７８℃Ｏ奮分を採つえ。こ
れにヘキサノを加えて攪拌し、析出する結晶を集め、こ
れをヘプタン：エタノール−４：ｌ）温舎薯媒６ｅ−よ
）再結晶すると２るＩの目的物、即ト直ｐ−グービルフ
ェニル）−１，８−ジオキナ−２−オンを得九ａｍ−ｐ
、は９６．６〜９７、６ ”Ｄで、そのＮＭＲスペクト
ル及び赤外線徴収スペクトルは目的物の構造式と矛盾し
ないもＯであった。又、その元素分析値は次の如く運論
値とよく一致して−る。Pengzen's) OII-made)
P-844~II! 11.7°C) Sof, diethyl carbonate 61f and sodium ethoxide lf were placed in a distillation flask and heated, the ethanol produced was distilled off, and the distillate was heated until the liquid temperature reached 140" OK, and further heated at 100°C for 3 hours. After heating, remove diethyl carbonate under reduced pressure at -11°C, and then distill while depolymerizing under reduced pressure at -178°C. Add hexano to this and stir, collect the precipitated crystals, and recrystallize them with heptane:ethanol-4:l) warm-temperature medium 6e-) to obtain the desired product in 2. Bilphenyl)-1,8-dioquina-2-one was obtained from nine am-p
, was 96.6 to 97.6"D, and its NMR spectrum and infrared collection spectrum were O, which is consistent with the structural formula of the target product. Also, its elemental analysis value is similar to the luck value as shown below. It's in agreement.
分析値 履論値（ＣｉＨｔ・０１として）Ｃ丁（１４
％ 丁Ｑ、魯魯％
ＨＴ、４％ ７．８２％
夷麹儒１１．比較例−〜畠
Ｃｓ＆＜コＨこ刈ＣＮ ８部（重量、以下同様
）Ｃ１烏１（−８夕％ＣＮ ４・部Ｃ１九＠（
祭Ｈこ％ｃＮ ｚｒｌｌＣｓＩｂｙＯ＆ン
１６部 ′ＣＣ１０ニド（）【にトＣ）１ １
１１１からなる液晶龜成物ム０Ｎ−Ｉ点は暮８℃であ為
が″、これに（璽）式の化合物及び比較Ｏえめ、従来、
電圧低下剤として使用畜れ七い丸化舎物を夫々Ｓ重量％
添加しえ液晶組成愉を作如、それをＭｖ＆で得られ為〒
Ｎｍ１表示素予め遭遇光量の電Ｅ健喜像を一定しえ。そ
の結果をｊｌＩ１表に示す。嬉１表に旋てＶｔｏ ＊
Ｖｉａ ＊ Ｖｗは夫々ＩＩ湯光量が、そＯ亀和値ａｘ
ｅ％、６０％、−０％に達する時の電圧を示し、■１・
はしきい値電圧、Ｖよ飽和電圧である。又Ｖｕ ／ Ｖ
ｕ・は透過光量−電圧一一における急峻度を示し、この
値が小さい程急唆度が高く、グイナ電ツク駆動するのに
適していることを示している。Analytical value Logical value (as CiHt・01)C (14
% Ding Q, Lu Lu% HT, 4% 7.82% Yi Koji 11. Comparative example - ~ Hatake Cs &<KoH Kokari CN 8 parts (weight, same below) C1 Karasu 1 (-8 evening% CN 4 parts C19@(
FestivalH%cN zrllCsIbyO＆N
Part 16 'CC10 Nido () [NitoC) 1 1
The 0N-I point of the liquid crystal compound consisting of 111 is at 8°C.
S weight% of each of the seven rounded animals used as a voltage lowering agent
Additions can be made to the liquid crystal composition, and it can be obtained with Mv&.
Nm1 Display Element Set the electric E Kenki image of the encounter light amount in advance. The results are shown in Table jlI1. Happy 1st turn Vto *
Via * Vw is II water light amount, so O Kame sum value ax
Indicates the voltage when reaching e%, 60%, -0%, ■1.
is the threshold voltage, and V is the saturation voltage. Also Vu/V
u. represents the steepness of the amount of transmitted light minus the voltage, and the smaller this value is, the higher the steepness is, indicating that it is suitable for driving a Guinea electric current.
ＪＩＩ１表かられかる様Ｋ（１）式の化合物をわずか６
重量％添加しただけでｙｌ・が０．１〜０−ＳＶ低くな
っている。６−置換基〇−憂が長くなる。と共忙しきｉ
値電圧などの低下の°度合−小さ≦なっているがそれで
も比較例の化合物に比較して遜色はない、ｉ良ｖ１へ１
・０値も小さくなって急峻度は高くなっている。From the JII1 table, only 6 compounds of formula K (1) were found.
Just by adding % by weight, yl• is lowered by 0.1 to 0-SV. 6-Substituent〇-The sadness becomes longer. I'm busy with you
The degree of decrease in voltage, etc. is small ≦, but it is still comparable to the comparative example compound, i.e. good v1 to 1
・The 0 value is also smaller and the steepness is higher.
実施例Ｔ〜１２
液晶組成物人以外の６種Ｏｆ！ａ組威物（母液晶）Ｋつ
ｈて（１）式の化合物として６−ブロビルー１．１−ジ
オキナ−２−オンを５重量％添加しえものと添加しない
ものとについて実施例３〜、・と同様にして透過光量−
電圧特性を一定した。そＯＩＩ定結果を菖８表に示す、
第２表に於て、液晶組威物ＢとはＲ４ＣＮと
物ＣとはＲ−ＧΣＣｏｏ＜ンＣＮと
親戚物νはＲ（合（ンＯＲ’とＲ（姶（）（ンＲ′”０
ＩＩＩＬ威物であり、液晶組成物Ｇ輪 □Ｒ
÷←Ｃ００ＱＯＲ’の組成物であり、以上のうちｌ−Ｅ
はΔＣが正０ものであるが・ｒ、Ｇは６層が６に近いか
負の値をもつものである。い゛ずれの化合物も現在実用
に供されて−る液晶Ｏ代表的なものである。Examples T~12 Liquid crystal compositions of 6 types other than humans! Examples 3 to 6-brobyl-1,1-dioquina-2-one with and without addition of 5% by weight of 6-brobyl-1,1-dioquina-2-one as a compound of formula (1) (a) (mother liquid crystal),・Similarly to the amount of transmitted light -
The voltage characteristics were kept constant. The OII results are shown in Table 8.
In Table 2, liquid crystal assembly B is R4CN and C is R-GΣCoo
IIIL is a masterpiece, liquid crystal composition G ring □R
It is a composition of ÷←C00QOR', and among the above, l-E
ΔC is positive 0, but r and G are close to 6 in 6 layers or have negative values. Both of these compounds are representative of liquid crystal O currently in practical use.
１８２表、
＊母液晶Ｆ、ＧはΔｇが正で−ないのでそめままではＴ
Ｎ表示素子を作る−とは出来ない。Table 182, *For the mother liquid crystals F and G, Δg is positive and not -, so if it is left as it is, T
It is not possible to make N display elements.
Ｓ意表から現在実用に供されている大部分の液晶につい
て０）式の化合物を添加することによ）ＶＭ（Ｌ、きい
値電圧）を下げることがわかり、又親戚物Ｆ、Ｇ（ΔＣ
■−１１）のごときΔＣが負Ｏものに添加してもΔＣが
正となってＴＮ嵩子ＫＩ！用することが可能となる。From the table of results, it was found that by adding a compound of formula 0) to most of the liquid crystals currently in practical use, VM (L, threshold voltage) can be lowered, and relatives F and G (ΔC
■-11) Even if ΔC is added to a negative O material, ΔC becomes positive and TN Takako KI! It becomes possible to use it.
実施例１３
Ｃ晶−Ｑ−ＣＯＯ−Ｑ−ＣＮ １・郁Ｃ１＆
＜ン（ンＣＮ １６部からなる液晶
組成物ＨはＮ−Ｉ点が７８℃で、し亀−値電圧Ｖｌ・が
ＬＩＶ％飽和電圧Ｖｓが１．５Ｖである。この液晶組成
物Ｈに（１）式の１．８−ジオキナ−２−オン４ｓおよ
びｂ−プロピル−１，１−ジオキナ−２−オン２部を添
加すると）ｉ−ＩＪＬａ６０℃＠ Ｖｉａは０．７８Ｖ
、Ｖｓｏａｉ、ｔｓｖといずれも低くなった。この組成
物を用いてＴＮＩＩ表示素子を作Ｊ）、１／２デユーテ
イ、１／２バイアスのダイナ建ツク駆動を行なうと動作
電圧が１．６Ｖで５〜８６℃での動作マージンは２％で
あった。Example 13 C crystal-Q-COO-Q-CN 1・Iku C1&
A liquid crystal composition H consisting of 16 parts of CN has an N-I point of 78°C and a peak voltage Vl of LIV% and a saturation voltage Vs of 1.5V. 1) When 2 parts of 1,8-dioquina-2-one of formula 4s and b-propyl-1,1-dioquina-2-one are added) i-IJLa60℃@Via is 0.78V
, Vsoai, and tsv all became low. When a TNII display element was fabricated using this composition and driven by a 1/2 duty, 1/2 bias dynamic structure, the operating voltage was 1.6 V and the operating margin at 5 to 86°C was 2%. there were.
このように１．６■でダイナ建ツク駆動できることは、
従来の液晶組成物ではなし得なかつえことであ夛、その
意義は非常に大きい。In this way, the ability to drive the dynamo with 1.6mm is as follows:
This is of great significance because it cannot be achieved with conventional liquid crystal compositions.
実施１１１４
ＣａＨｅ噂へ０００（）ＯＣｎＨ鯖１
（！１−ｍ１ ｍ ２ ｓ ４のもの同量混合物）
６７部Ｃ５Ｈｖ８ＣＯＯ（）ＯＣＣ１０９部
ＣｍＨｓｓ ＋ Ｃ００ＧＣＨｓ ４部
ｃｍ＆ＱｃｏｏＱｃＮｓ部
ＣＲＨ耐ｌ■Ｘ）ｃｏｏＨＣＮ
（１諷８．６） ６部
からなる液晶組成物ＪＦｉＮ−Ｉ点が６９℃でしきい値
電圧がｔＯＶ、飽和電圧が２．９Ｖである。Implementation 1114 CaHe rumor 000 ()OCnH mackerel 1 (!1-m1 m2s4 mixture of equal amounts)
67 parts C5Hv8COO () OCC109 parts CmHss + C00GCHs 4 parts cm&QcooQcNs part CRH resistance l X) cooHCN (1 8.6) Liquid crystal composition consisting of 6 parts JFiN-I point is 69°C, threshold voltage is tOV, The saturation voltage is 2.9V.
ζｅｔａ銀威物Ｊ−６部に（１）式ＯＳ−グービルー１
．■−ジオ命ナー霊−オンを４部添加するとＮ−Ｉ点紘
６！６℃にな〕、これを使用して作りえＴＮ表示嵩子Ｏ
Ｖ輸ｄ １．６ Ｖ 、 ＶＭは１１Ｖといずれも低く
なりえ、又組成物ＪＯＶジＶｍＩＩｉ１．４＆であるの
に対し、６−プロピル−１゜１−ジオキナ−２−オンを
添加し九組成物では１、魯８と１）、かｔｅ急唆装が向
上し丸、このような急峻度がｍ−液晶組成物を使用すれ
にデ瓢−テイ比の高％Ａ１１ｌ晶表示素子を作ることか
で１１為。ζeta Silver Power J-6 Part (1) Formula OS-Gooby Lou 1
．． ■ - Adding 4 parts of Geo-Meiner Rei-on brings the temperature to N-I to 6!6℃].
Both Vd 1.6 V and VM can be as low as 11 V, and while the composition JOV diVmIIi 1.4 & 6-propyl-1°1-dioquina-2-one is added, the 9 composition In terms of 1, 8 and 1), it has been suggested that the sharpness of the crystal will be improved, and such a steepness can be used to make a high percentage A11L crystal display device with a high density ratio. Kade 11.
実施例ｌ５
Ｃａ＆８ＣＯＯｕＯＣ山叶ｌ
（ｍ −ｉ ｏ！、４０％の同量混合物） 尋１
部Ｃｓ＆ＯＨｃｏｏ登ＯＣ晶Ｉ Ｉ＊
からナル液晶組成物ＫＩＩｉＮ−１点１ Ｂ ”１０−
Ｔｗ。Example 15 Ca & 8COOuOC Yamaha 1 (m-i o!, 40% mixture of equal amounts) 1 fathom
Part Cs & OHcoo OC crystal II I* to null liquid crystal composition KIIiN-1 point 1 B "10-
Tw.
ａ ｌ ＠ Ｖ 、 Ｖｗ社Ｌ ８ ｔｓ Ｖ テＶｓ
／Ｙｎは１．１６である。この液晶組威吻に１１７部Ｋ
（１）式Ｏ６−メチルー１．ｓ−ジオキナ−２−オンを
８ｓ添加するとＮ＝夏点は６２℃ｅ Ｖｔ＠は１． ＠
Ｖ −ＶＭはＬ Ｉ Ｖ 、 Ｖ＠／Ｖｔ＠は１．１
畠とｔつた。コノようにわずか８％添加し丸だけでｖｌ
・およびＶＭが非常に低下するとともに、急峻度が向上
した。a l @ V , Vw L 8 ts V te Vs
/Yn is 1.16. 117 part K to this liquid crystal group majesty
(1) Formula O6-methyl-1. When s-dioquina-2-one is added for 8 seconds, N=summer point is 62℃e and Vt@ is 1. @
V - VM is L I V, V@/Vt@ is 1.1
I hung out with Hatake. Just like Konoyo, only 8% is added and the vl is just round.
・The VM and VM were greatly reduced and the steepness was improved.
（従来のもので１ｉＶｔ・、■鱒を低下させるとＶジｖ
ＳＩが大暑くなる傾向が６つ九、）以上(With the conventional one, it is 1iVt・, ■ When the trout is lowered, Vziv
The tendency for SI to become extremely hot is 6% or more.
Claims (1)
あ゛る） で表わされる５−置換−１，暑−ジオ會す−２−オンの
少なくと４１１ｔｌ−＠ｏ重量％會膚してなるネマチッ
ク液晶組成物。[Scope of Claims] A 5-substituted-1, 2-2-one, represented by the general formula (in the above formula, ml1.~34th)%, where m is . A nematic liquid crystal composition comprising at least 411 tl-@o% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1712482A JPS58136680A (en) | 1982-02-05 | 1982-02-05 | Nematic liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1712482A JPS58136680A (en) | 1982-02-05 | 1982-02-05 | Nematic liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58136680A true JPS58136680A (en) | 1983-08-13 |
| JPH0160076B2 JPH0160076B2 (en) | 1989-12-20 |
Family
ID=11935280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1712482A Granted JPS58136680A (en) | 1982-02-05 | 1982-02-05 | Nematic liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58136680A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0144648A2 (en) * | 1983-11-02 | 1985-06-19 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Liquid crystals: derivatives of cyclohexylbenzene and cyclohexylbiphenyl |
| US4615824A (en) * | 1983-12-22 | 1986-10-07 | Veb Werk Fuer Fernsehelektronik Im Veb Kombinat Mikroelektronik | Mixing component for liquid crystal substances |
| US4707296A (en) * | 1984-08-16 | 1987-11-17 | Chisso Corporation | Alkoxyethoxybenzoic acid ester derivatives |
| US4751017A (en) * | 1985-03-22 | 1988-06-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Heterocyclic boron compounds |
| CN106987255A (en) * | 2016-01-21 | 2017-07-28 | 三星显示有限公司 | Liquid-crystal composition including its Liquid crystal disply device and its preparation method |
| WO2017208953A1 (en) * | 2016-06-03 | 2017-12-07 | Dic株式会社 | Spontaneous orientation aid for liquid crystal composition, compound suitable for said spontaneous orientation aid, liquid crystal composition, and liquid crystal display element |
-
1982
- 1982-02-05 JP JP1712482A patent/JPS58136680A/en active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0144648A2 (en) * | 1983-11-02 | 1985-06-19 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Liquid crystals: derivatives of cyclohexylbenzene and cyclohexylbiphenyl |
| US4652089A (en) * | 1983-11-02 | 1987-03-24 | Hoffmann-La Roche Inc. | Liquid crystalline compounds and mixtures |
| US4615824A (en) * | 1983-12-22 | 1986-10-07 | Veb Werk Fuer Fernsehelektronik Im Veb Kombinat Mikroelektronik | Mixing component for liquid crystal substances |
| US4707296A (en) * | 1984-08-16 | 1987-11-17 | Chisso Corporation | Alkoxyethoxybenzoic acid ester derivatives |
| US4751017A (en) * | 1985-03-22 | 1988-06-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Heterocyclic boron compounds |
| CN106987255A (en) * | 2016-01-21 | 2017-07-28 | 三星显示有限公司 | Liquid-crystal composition including its Liquid crystal disply device and its preparation method |
| CN106987255B (en) * | 2016-01-21 | 2022-04-15 | 三星显示有限公司 | Liquid crystal composition, liquid crystal display device comprising same, and method for manufacturing same |
| WO2017208953A1 (en) * | 2016-06-03 | 2017-12-07 | Dic株式会社 | Spontaneous orientation aid for liquid crystal composition, compound suitable for said spontaneous orientation aid, liquid crystal composition, and liquid crystal display element |
| JPWO2017208953A1 (en) * | 2016-06-03 | 2018-11-08 | Dic株式会社 | Spontaneous alignment aid for liquid crystal composition, compound suitable for spontaneous alignment aid, liquid crystal composition, and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0160076B2 (en) | 1989-12-20 |
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