JPH04210668A - Ether based liquid crystal compound for lowering threshold voltage - Google Patents
Ether based liquid crystal compound for lowering threshold voltageInfo
- Publication number
- JPH04210668A JPH04210668A JP40107890A JP40107890A JPH04210668A JP H04210668 A JPH04210668 A JP H04210668A JP 40107890 A JP40107890 A JP 40107890A JP 40107890 A JP40107890 A JP 40107890A JP H04210668 A JPH04210668 A JP H04210668A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound expressed
- compound
- liquid crystal
- threshold voltage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 55
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 abstract description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000564 Raney nickel Inorganic materials 0.000 abstract description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- -1 useful for 5TN-LCD Chemical class 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical class C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
［０００１１ [00011
【産業上の利用分野］本発明は、電気光学的表示材料と
して有用なエーテル系液晶化合物に関し、更に詳しくは
液晶表示装置に有用なエーテル系液晶化合物に関する。
［０００２］
【従来の技術】液晶表示セルの代表的なものにＴＮ−Ｌ
ＣＤ （ツィステッド・ネマチック液晶表示装置）があ
り、時計、電卓、電子手帳、ポケットコンピュータ、ワ
ードプロセッサ、パーソナルコンピュータなどに使用さ
れている。近年、ＯＡ種機器処理情報の増加に伴い、画
面に表示される情報量が増大しており、従来のＴＮ−Ｌ
ＣＤではコントラスト及び視野角等の表示品位面から、
特にワードプロセッサ、パーソナルコンピュータなどの
高時分割駆動の要求に応えられなくなっている。
（０００３］このような状況の中で、シエファ−（Ｓｃ
ｈｅｆｆｅｒ）等［ＳＩＤ ’ ８５ Ｄｉｇｅｓ ｔ
、ＰＬ２０ （１９８５） 〕あるいは衣川等［：ＳＩ
Ｄ ’８６ Ｄｉｇｅｓ ｔ、 Ｐ１２２ （１９８６
） 〕によってＳＴＮ （スーパー・ツィステッド・ネ
マチック）−ＬＣＤが開発され、ワードプロセッサ、パ
ーソナルコンピュータなどの高情報処理用の表示に広く
普及しはじめている。
［０００４］[Field of Industrial Application] The present invention relates to an ether-based liquid crystal compound useful as an electro-optical display material, and more particularly to an ether-based liquid crystal compound useful for a liquid crystal display device. [0002] [0002] TN-L is a typical liquid crystal display cell.
There is a CD (twisted nematic liquid crystal display), which is used in watches, calculators, electronic notebooks, pocket computers, word processors, personal computers, etc. In recent years, with the increase in information processed by OA type equipment, the amount of information displayed on the screen has increased, and conventional TN-L
For CDs, in terms of display quality such as contrast and viewing angle,
In particular, it is no longer possible to meet the demands for high time division drive of word processors, personal computers, and the like. (0003) In this situation, Schiefer (Sc
heffer) etc. [SID' 85 Digest
, PL20 (1985)] or Kinugawa et al. [:SI
D '86 Digest, P122 (1986
)] developed STN (super twisted nematic)-LCD, and it has begun to be widely used as a display for high information processing such as word processors and personal computers. [0004]
【発明が解決しようとする課題］ ５ＴＮ−ＬＣＤに特
に有用な液晶化合物の一つとして、
［０００５］
【化２】
一般式
（０００６］ （式中、Ｒは直鎖状アルキル基を表わ
す。）で表わされる化合物（以下、ＰＣＨという。）が
知られている。ＰＣＨは正の誘電率の異方性を有するＰ
形の液晶化合物として有用であるが、誘電率の異方性（
△ε）の値が約＋１２〜１３とさほど大きくなく、現在
汎用されているネマチック液晶材料に混合した際に、液
晶材料のしきい値電圧の低下効果が小さいという欠点を
有している。
［０００７］本発明が解決しようとする課題は、ＰＣＨ
と類似の化学構造を有し、△εの値が大きく、現在汎用
されているネマチック液晶材料に混合した際に、液晶材
料のしきい値電圧の低下効果が大きな化合物を提供する
ことにある。
［０００８］[Problems to be Solved by the Invention] As one of the liquid crystal compounds particularly useful for 5TN-LCD, [0005] [Formula 2] General formula (0006] (wherein, R represents a linear alkyl group) A compound represented by (hereinafter referred to as PCH) is known. PCH has a positive dielectric constant anisotropy.
It is useful as a liquid crystal compound of the shape, but the anisotropy of the dielectric constant (
The value of Δε) is not so large, about +12 to 13, and it has the disadvantage that when mixed with currently widely used nematic liquid crystal materials, the effect of lowering the threshold voltage of the liquid crystal material is small. [0007] The problem to be solved by the present invention is that PCH
The object of the present invention is to provide a compound having a chemical structure similar to that of the present invention, having a large value of Δε, and having a large effect of lowering the threshold voltage of the liquid crystal material when mixed with the currently widely used nematic liquid crystal material. [0008]
【課題を解決するための手段】本発明は、上記課題を解
決するために、一般式（Ｉ）
［０００９］[Means for Solving the Problems] In order to solve the above problems, the present invention provides general formula (I) [0009]
【化３】
ＲＯ→ＣＨ）−−ぐりΣｃＨｔｃＨｔ−＠ｌｃＮ 、、
・（１）［００１０１（式中、Ｒは炭素原子数１〜５の
直鎖状アルキル基を表わし、ｎは１〜７を表わし、シク
ロヘキサン環はトランス配置をである。）で表わされる
化合物を提供する。本発明に係わる一般式（Ｉ）で表わ
される化合物は、次の製造方法に従って製造することが
できる。
［００１１１[Chemical 3] RO→CH) --Guri ΣcHtcHt-@lcN ,,
・(1) A compound represented by [00101 (wherein, R represents a linear alkyl group having 1 to 5 carbon atoms, n represents 1 to 7, and the cyclohexane ring has a trans configuration) provide. The compound represented by general formula (I) according to the present invention can be produced according to the following production method. [00111
【化４］
・・・（１ｍ）
第１段階
・・・（ＩＩＩ）
第２段階
・・・（ＩＶ）
・・・ｆｆ）
第３Ｗｋ階
・・・（ｖ１］
１４段階
・・・（り
［００１２］ （上記反応式におけるＲ及びｎは、式
（Ｉ）におけるＲ及びｎと同様の意味を有し、φはフェ
ニル基を表わす。）第１段階二式（ＩＩ）の化合物をト
ルエン中トリフェニルホスフィンと反応させて、式（Ｉ
ＩＩ）の化合物を製造する。第２段階二式（ＩＩＩ）の
化合物とテトラヒドロフラン中、カリウム−１−ブトキ
サイドの如き強塩基で処理し、ｗ： ｔ ｔ ｉｇ試薬
とした復式（ＩＶ）の化合物と反応させて（Ｖ）の化合
物を製造する。
［００１３］ 第３段階二式（Ｖ）の化合物を酢酸エ
チル中、ラネーニッケルを触媒として接触還元し、式（
Ｖｌ）の化合物を製造する。第４段階：式（Ｖｌ）の化
合物をジメチルホルムアミド中、シアン化第−銅と反応
させて、式（Ｉ）の化合物を製造する。斯くして製造さ
れた本発明に係わる一般式（Ｉ）で表わされる化合物の
相転移温度を第１表に掲げる。
［００１４］
【表１】
第
表
［００１５］ （表中、Ｃは結晶相、Ｎはネマチック
相、■は等方性液体相を各々表わす。）一般式（Ｉ）の
化合物と混合して使用することのできる好ましい液晶化
合物の代表例としては、例えば、４−置換安息香酸４°
−置換フェニルエステル、４−置換シクロヘキサンカル
ボン酸４゛−置換フェニルエステル、４−置換シクロヘ
キサンカルボン酸４°−置換ビフェニルエステル、４−
（４−置換シクロヘキサンカルボニルオキシ）安息香酸
４゛−置換フェニルエステル、４−（４−置換シクロヘ
キシル）安息香酸４゛−置換フェニルエステル、４−
（４−置換シクロヘキシル）安息香酸４”−置換シクロ
ヘキシルエステル、４−置換４゛−置換ビフェニル、４
−置換フェニル−４°−置換シクロヘキサン、４−置換
４°゛置換ターフエニル、４−置換ビフェニル４°−置
換シクロヘキサン、２−（４−置換フェニル）−５−置
換ピリミジンなどを挙げることができる。
（００１６］第２表はネマチック液晶材料として現在汎
用されている混合液晶（Ａ）の７０重量％と一般式（Ｉ
）で表わされる化合物のＮｏ、 １の化合物の各々３０
重量％から成る混合液晶の誘電率の異方性（△ε）とし
きい値電圧（Ｖｔｈ）を掲示し、比較のために混合液晶
（Ａ）自体の△εと、混合液晶（Ａ）の７０重量％と、
一般式（Ｉ）で表わされる化合物と類似構造を有する下
記式（ａ）の化合物及び式（ｂ）の化合物の各々３０重
量％から成る各混合液晶の△εとｖｔｈを掲示したもの
である。
［００１７］尚、混合液晶（Ａ）は、
［００１８］[C4] ...(1m) 1st stage...(III) 2nd stage...(IV) ...ff) 3rd Wk floor...(v1) 14th stage...(ri[ [0012] (R and n in the above reaction formula have the same meanings as R and n in formula (I), and φ represents a phenyl group.) In the first step, the compound of formula (II) is dissolved in toluene. By reacting with phenylphosphine, the formula (I
The compound II) is produced. In the second step, the compound of formula (III) is treated with a strong base such as potassium-1-butoxide in tetrahydrofuran and reacted with the compound of formula (IV) as a w: t t ig reagent to form the compound of (V). Manufacture. [0013] In the third step, the compound of formula (V) was catalytically reduced in ethyl acetate using Raney nickel as a catalyst to obtain the formula (
Vl) is prepared. Fourth step: The compound of formula (Vl) is reacted with cupric cyanide in dimethylformamide to produce the compound of formula (I). Table 1 lists the phase transition temperatures of the compounds represented by the general formula (I) according to the present invention thus produced. [0014] [Table 1] Table [0015] (In the table, C represents a crystalline phase, N represents a nematic phase, and ■ represents an isotropic liquid phase.) Used by mixing with a compound of general formula (I) Representative examples of preferred liquid crystal compounds that can be used include, for example, 4-substituted benzoic acid 4°
-Substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-substituted biphenyl ester, 4-
(4-Substituted cyclohexanecarbonyloxy)benzoic acid 4'-substituted phenyl ester, 4-(4-substituted cyclohexyl)benzoic acid 4'-substituted phenyl ester, 4-
(4-substituted cyclohexyl)benzoic acid 4''-substituted cyclohexyl ester, 4-substituted 4''-substituted biphenyl, 4
Examples include -substituted phenyl-4°-substituted cyclohexane, 4-substituted 4°-substituted terphenyl, 4-substituted biphenyl-4°-substituted cyclohexane, and 2-(4-substituted phenyl)-5-substituted pyrimidine. (0016) Table 2 shows 70% by weight of mixed liquid crystal (A), which is currently widely used as a nematic liquid crystal material, and the general formula (I
) No. 1 of the compound represented by 30 each of the compounds of 1
The dielectric constant anisotropy (△ε) and threshold voltage (Vth) of the mixed liquid crystal consisting of % by weight are posted, and for comparison, △ε of the mixed liquid crystal (A) itself and 70% of the mixed liquid crystal (A) are shown. weight% and
Δε and vth of each mixed liquid crystal consisting of 30% by weight of each of the compound of the following formula (a) and the compound of the formula (b) having a similar structure to the compound represented by the general formula (I) are displayed. [0017] The mixed liquid crystal (A) is [0018]
【化５】
［００１９］から成るものであり、式（ａ）及び式（ｂ
）の化合物は、各々次式で表わされる化合物である。
［００２０１[0019], and the formula (a) and the formula (b
) are each represented by the following formula. [00201
【化６］
［００２１］
【表２】
第
表
混合液晶
誘電ｌ１ｌｏ異方性
し自い値電圧（Ｖ）
（Ａ）
−１，３
（＾）＋１１ｍ１
７．１
１．３８
（ム）十−２
６，８
１，４３
（Ａ）＋（ａ）
１．１
Ｚ、ａａ
（轟）十（ｂ）
１．８
２．１８
［００２２］第２表に掲示したデータから、一般式（Ｉ
）で表わされる化合物は、負の誘電率の異方性を有する
混合液晶（Ａ）に加えた時に、誘電率の異方性を増加さ
せ、しきい値電圧を低下させる効果を有することが理解
できる。構造類似で一般的に広く用いられている式（ａ
）の化合物を混合液晶（Ａ）に加えた時と比較すると、
誘電率の異方性も大きく、しきい値電圧が顕著に低いこ
とが明確である。
［００２３］本発明が容易に類推できないことは一般式
（Ｉ）で表わされる化合物と類似の構造を有する式（ｂ
）の化合物のしきい値電圧の低下効果が、本発明の化合
物Ｎｏ、 １よりも顕著に小さいばかりでなく、式（ａ
）の化合物よりも小さいことからも理解できる。
［００２４］[Chemical formula 6] [0021] [Table 2] Table Mixed liquid crystal dielectric l1lo Anisotropic free value voltage (V) (A) -1,3 (^) +11m1 7.1 1.38 (mu) 10- 2 6,8 1,43 (A) + (a) 1.1 Z, aa (Todoroki) 10 (b) 1.8 2.18 [0022] From the data posted in Table 2, the general formula (I
) is understood to have the effect of increasing the dielectric anisotropy and lowering the threshold voltage when added to the mixed liquid crystal (A) having negative dielectric anisotropy. can. The generally widely used formula (a
) is added to the mixed liquid crystal (A),
It is clear that the anisotropy of the dielectric constant is large and the threshold voltage is significantly low. [0023] The present invention cannot be easily analogized to compounds of formula (b) having a similar structure to the compound represented by general formula (I).
Not only is the threshold voltage lowering effect of the compound of formula (a) significantly smaller than that of compound No. 1 of the present invention, but also
), which can be understood from the fact that it is smaller than the compound. [0024]
【実施例】 （実施例１） 式 ％式％］[Example] (Example 1) formula %formula%]
【７】
（００２６］の化合物２６．８ｇ （０，１モル）をト
ルエン２０Ｏｎ＋１に溶解し、この溶液にトリフェニル
ホスフィン２６．３ｇ（０，１モル）を添加した後、３
時間加熱還流した。反応混合物を冷却した後、析出した
結晶を濾別し、真空乾燥させて下記化合物４８．５ｇ
（０，０９１モル）を得た。
［００２７］[7] 26.8 g (0.1 mol) of the compound (0026) was dissolved in 20 On+1 toluene, and 26.3 g (0.1 mol) of triphenylphosphine was added to this solution.
The mixture was heated to reflux for an hour. After cooling the reaction mixture, the precipitated crystals were filtered and dried under vacuum to obtain 48.5 g of the following compound.
(0,091 mol) was obtained. [0027]
【化８】
［００２８］上記化合物４８．５ｇ （０，０９１モル
）をテトラヒドロフラン２５０ｍ１に加え、−５℃に冷
却し、カリウムｔ−ブトキサイド１３．５ｇ （０，１
２モル）で処理した後、室温で１時間反応させた。反応
混合物を一５℃に冷却した後、反応混合物に式
％式％］[0028] 48.5 g (0,091 mol) of the above compound was added to 250 ml of tetrahydrofuran, cooled to -5°C, and 13.5 g (0,1 mol) of the above compound was added to 250 ml of tetrahydrofuran.
2 mol) and then allowed to react at room temperature for 1 hour. After cooling the reaction mixture to -5°C, the reaction mixture was added to the formula % formula %]
【９】
［００３０１の化合物１４．２ｇ （０，０８モル）の
テトラヒドロフラン溶液８０Ｉ１１１を滴下し、室温で
２時間反応させた。
反応終了後、反応混合物に水２５０ｍ ｌを加え、酢酸
エチル１５０ｍ ｌで３回抽出し、抽出液を水洗、乾燥
させた後、溶媒を減圧留去した。得られた残渣をトルエ
ン１００ｍ１に溶解し、同量のヘキサンを加えてトリフ
ェニルホスフィンオキサイドを析出させた。析出物を濾
別し、濾液を減圧濃縮した。得られた残渣をシリカゲル
カラムクロマトグラフィーを用いて精製して、下記化合
物１９．４ｇ （０，０５５モル）を得た。
［００３１１[9] A solution of 14.2 g (0.08 mol) of the compound 00301 in tetrahydrofuran 80I111 was added dropwise, and the mixture was reacted at room temperature for 2 hours. After the reaction was completed, 250 ml of water was added to the reaction mixture, and the mixture was extracted three times with 150 ml of ethyl acetate. The extract was washed with water, dried, and then the solvent was distilled off under reduced pressure. The obtained residue was dissolved in 100 ml of toluene, and the same amount of hexane was added to precipitate triphenylphosphine oxide. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified using silica gel column chromatography to obtain 19.4 g (0,055 mol) of the following compound. [00311
【化１０］
［００３２］上記化合物１９．４ｇ （０，５５モル）
を酢酸エチル１８０ｍ１に溶解し、ラネーニッケル２ｇ
を触媒として水素圧５ｋｇ／ｃｎｉ３．６０℃で５時間
接触還元した。反応終了後、触媒を濾別し、濾液を減圧
濃縮して下記化合物１８．８ｇ（０，０５３モル）を得
た。
［００３３］
【化１１】
［００３４］上記化合物１８．８ｇ （０，５３モル）
をＮ、 Ｎ−ジメチルホルムアミド１２０ｍ１に溶解し
、この溶液にシアン化第１銅５．４ｇ （０，０６モル
）を加えた後、６時間加熱還流させた。反応終了後、反
応混合物にアンモニア水１５０騰ｌを加えた後、酢酸エ
チル１５０ｍ１で２回抽出し、抽出液を水洗、乾燥させ
た後、溶媒を減圧留去した。得られた残渣をエタノール
から再結晶させて精製して、下記化合物１２．３ｇ （
０，０４１モル）を得た。
［００３５］[Chemical formula 10] [0032] 19.4 g (0.55 mol) of the above compound
was dissolved in 180ml of ethyl acetate, and 2g of Raney nickel was added.
was used as a catalyst for catalytic reduction at a hydrogen pressure of 5 kg/cni at 3.60° C. for 5 hours. After the reaction was completed, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure to obtain 18.8 g (0,053 mol) of the following compound. [0033] [0034] 18.8 g (0.53 mol) of the above compound
was dissolved in 120 ml of N,N-dimethylformamide, and 5.4 g (0.06 mol) of cuprous cyanide was added to this solution, followed by heating under reflux for 6 hours. After the reaction was completed, 150 liters of aqueous ammonia was added to the reaction mixture, which was extracted twice with 150 ml of ethyl acetate. The extract was washed with water, dried, and the solvent was distilled off under reduced pressure. The obtained residue was purified by recrystallization from ethanol to obtain 12.3 g of the following compound (
0,041 mol) was obtained. [0035]
【化１２】
転移温度
４３℃（Ｃ呻！）
１２℃（１ジＮ）
（００３６］ （実施例２）実施例１において、式％
式％］[Chemical formula 12] Transition temperature 43°C (C groan!) 12°C (1 diN) (0036] (Example 2) In Example 1, the formula %
formula%]
【１３】 ［００３８］の化合物に代えて式 ［００３９］[13] In place of the compound of [0038], the formula [0039]
【化１４】
（００４０１の化合物１６．５ｇ （０，０８モル）を
使用した以外は、実施例１と同様にして下記化合物を得
た。
［００４１１embedded image The following compound was obtained in the same manner as in Example 1 except that 16.5 g (0.08 mol) of the compound 00401 was used.
【化１５］
転移温度
４７℃
（Ｃ呻Ｉ）
１４℃゛（璽−Ｎ）
［００４２］
【発明の効果】本発明に係わる一般式（Ｉ）で表わされ
る化合物は、ＰＣＨと類似の化学構造を有し、しきい値
電圧の低下効果が小さいというＰＣＨの欠点を補なうも
のである。従って、本発明に係わる一般式（Ｉ）で表わ
される化合物は、ＴＮ−ＬＣＤあるいは５ＴＮ−ＬＣＤ
用の材料として極めて有用である。[Chemical formula 15] Transition temperature: 47°C (C-I) 14°C (N) [0042] [Effects of the invention] The compound represented by the general formula (I) according to the present invention has a chemical structure similar to that of PCH. This compensates for the drawback of PCH that the effect of lowering the threshold voltage is small. Therefore, the compound represented by the general formula (I) according to the present invention can be used for TN-LCD or 5TN-LCD.
It is extremely useful as a material for
Claims (1)
わし、ｎは１〜７の整数を表わし、シクロヘキサン環は
トランス配置である。）で表わされる化合物。[Claim 1] General formula [Chemical formula 1] ▲ Numerical formulas, chemical formulas, tables, etc. (wherein the cyclohexane ring is in the trans configuration).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP40107890A JPH04210668A (en) | 1990-12-10 | 1990-12-10 | Ether based liquid crystal compound for lowering threshold voltage |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP40107890A JPH04210668A (en) | 1990-12-10 | 1990-12-10 | Ether based liquid crystal compound for lowering threshold voltage |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04210668A true JPH04210668A (en) | 1992-07-31 |
Family
ID=18510937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP40107890A Pending JPH04210668A (en) | 1990-12-10 | 1990-12-10 | Ether based liquid crystal compound for lowering threshold voltage |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04210668A (en) |
-
1990
- 1990-12-10 JP JP40107890A patent/JPH04210668A/en active Pending
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