JP2701064B2 - Alkoxy tolan compounds - Google Patents
Alkoxy tolan compoundsInfo
- Publication number
- JP2701064B2 JP2701064B2 JP1026373A JP2637389A JP2701064B2 JP 2701064 B2 JP2701064 B2 JP 2701064B2 JP 1026373 A JP1026373 A JP 1026373A JP 2637389 A JP2637389 A JP 2637389A JP 2701064 B2 JP2701064 B2 JP 2701064B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- heptyloxy
- alkoxy
- tolan
- compound
- 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 - Fee Related
Links
- -1 Alkoxy tolan compounds Chemical class 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000004973 liquid crystal related substance Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical class C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 2
- ODEHKVYXWLXRRR-UHFFFAOYSA-N hex-3-yn-1-ol Chemical compound CCC#CCCO ODEHKVYXWLXRRR-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- YHYGSIBXYYKYFB-VOTSOKGWSA-N (2e)-octa-2,7-dien-1-ol Chemical compound OC\C=C\CCCC=C YHYGSIBXYYKYFB-VOTSOKGWSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- CCDJWJAXYAVWRJ-UHFFFAOYSA-N 4-[2-(4-heptoxyphenyl)ethynyl]phenol Chemical compound C1=CC(OCCCCCCC)=CC=C1C#CC1=CC=C(O)C=C1 CCDJWJAXYAVWRJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 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
- 210000004027 cell Anatomy 0.000 description 1
- 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 1
- 239000012769 display material Substances 0.000 description 1
- 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 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 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 1
- 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 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- 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 1
- 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 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- WLPYSOCRPHTIDZ-UHFFFAOYSA-N pent-2-yn-1-ol Chemical compound CCC#CCO WLPYSOCRPHTIDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000004079 stearyl 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])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)
Description
【発明の詳細な説明】 本発明は、電気光学的表示材料として有用なトラン化
合物に関し、さらに詳しくは、STN型液晶材料に混合す
ることによって液晶材料の屈折率の異方性を大きくする
のに有用なアルコキシトラン化合物に関するものであ
る。The present invention relates to a tolan compound useful as an electro-optical display material. More specifically, the present invention relates to a method for increasing the anisotropy of the refractive index of a liquid crystal material by mixing it with an STN type liquid crystal material. It relates to useful alkoxy tolan compounds.
現在、STN型液晶セルはグリーンまたはブルーモード
より白黒、フルカラー化へ向けて開発が進められてお
り、それと併行して動画対応への高速応答化の検討が進
められている。高速応答としては、従来、強誘電性液晶
が研究されているが、STN型液晶セルの層の厚さをより
薄くする事により、高速応答が期待される。その場合、
セルに充填される液晶材料の屈折率の異方性（Δｎ）の
大きな液晶材料が必要となり、その代表例として低粘性
にして高いΔｎを示す各種トラン化合物が提案されたが
まだ不十分であり、さらに高いΔｎを示す化合物が望ま
れていた。At present, STN-type liquid crystal cells are being developed toward black-and-white and full-color modes from green or blue mode, and at the same time, studies are underway on high-speed response to moving image support. As a high-speed response, ferroelectric liquid crystals have been studied, but a high-speed response can be expected by making the thickness of the STN-type liquid crystal cell thinner. In that case,
A liquid crystal material with a large refractive index anisotropy (Δn) of the liquid crystal material to be filled in the cell is required. As a typical example, various tolan compounds having a low viscosity and a high Δn have been proposed, but are still insufficient. And a compound exhibiting an even higher Δn have been desired.
本発明者等は、上記現状に鑑み、低粘度にして高いΔ
ｎを示す化合物を見出すべく鋭意検討を重ねた結果、次
の一般式（Ｉ）で表される新規なアルコキシトラン化合
物を液晶に添加することにより、液晶のΔｎを著しく改
良することを見出した。In view of the above-mentioned situation, the present inventors have set a low viscosity and a high Δ
As a result of intensive studies to find a compound showing n, it was found that adding a novel alkoxytolan compound represented by the following general formula (I) to the liquid crystal significantly improved the Δn of the liquid crystal.
（式中、Ｒは炭素原子数１〜18のアルキル基を示し、
Ｒ′は炭素原子数３〜17のアルキニル基またはアルカジ
エニル基を示す。） 本発明になる上記一般式（Ｉ）で表される化合物にお
いて、Ｒで示される炭素原子数１〜18のアルキル基とし
ては、例えば、メチル、エチル、プロピル、ブチル、ペ
ンチル、ヘキシル、ヘプチル、オクチル、ノニル、デシ
ル、ドデシル、テトラデシル、ヘキサデシル、オクタデ
シルなどがあげられ、またＲ′で示される炭素原子数３
〜17のアルキニル基としては、例えば、１−プロピニ
ル、１−ブチニル、２−ブチニル、１−ペンチニル、２
−ペンチニル、１−ヘキシニル、４−ヘプチニル、６−
オクチニル、６−ノニニル、７−ノニニル、８−ウンデ
シニル、10−トリデシニル、12−ペンタデシニルなどが
あげられ、アルカジエニル基としては、1,3−ブタジエ
ニル、1,6−ヘプタジエニル基などがあげられる。 (Wherein, R represents an alkyl group having 1 to 18 carbon atoms,
R 'represents an alkynyl group or an alkadienyl group having 3 to 17 carbon atoms. In the compound represented by the general formula (I) according to the present invention, examples of the alkyl group having 1 to 18 carbon atoms represented by R include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, Octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, etc., and the number of carbon atoms represented by R ′ is 3
And alkynyl groups such as 1-propynyl, 1-butynyl, 2-butynyl, 1-pentynyl, 2
-Pentynyl, 1-hexynyl, 4-heptynyl, 6-
Octynyl, 6-noninyl, 7-noninyl, 8-undecinyl, 10-tridecinyl, 12-pentadecynyl and the like are mentioned, and alkadienyl groups are 1,3-butadienyl and 1,6-heptadienyl groups.
また、上記一般式（Ｉ）で表される化合物は、Ｒ′−
CH2−OHで表されるアルコールと４−アルコキシ−４′
−ヒドロキシトランとを反応させることにより容易に製
造することができる。The compound represented by the above general formula (I) is a compound represented by R′-
Alcohol represented by CH 2 —OH and 4-alkoxy-4 ′
-Can be easily produced by reacting with -hydroxytolan.
かくして得られる本発明のアルコキシトラン化合物は
STN型液晶材料に混合することによって液晶材料の屈折
率の異方性を大きくするに有用なばかりでなく、反応性
に優れるため、各種の合成中間体として有用であり、特
に、液晶化合物として周知のアルコキシトラン化合物を
得るための中間体として有用である。The alkoxytolan compound of the present invention thus obtained is
When mixed with STN-type liquid crystal materials, it is useful not only for increasing the anisotropy of the refractive index of the liquid crystal material, but also because of its excellent reactivity, it is useful as various synthetic intermediates, especially well-known as a liquid crystal compound. Is useful as an intermediate for obtaining the alkoxytolan compound.
以下、実施例によって本発明を更に詳細に説明する。 Hereinafter, the present invention will be described in more detail with reference to examples.
実施例１ ４−ｎ−ヘプチルオキシ−４′−（2,7−オクタジエニ
ルオキシ）トランの合成 2,7−オクタジエン−１−オール0.07g（0.55mmol）、
４−ｎ−ヘプチルオキシ−４′−ヒドロキシトラン0.15
g（0.5mmol）およびトリフェニルホスフィン0.16gを乾
燥ジエチルエーテル1.5に溶解した後、ここにアゾジカ
ルボン酸ジイソブロピルエステル0.12gの0.5の乾燥ジエ
チルエーテル溶液を約３分間で滴下した。室温で3.5時
間撹拌した後、析出したトリフェニルホスフィンオキシ
ドをろ別し、ろ液を脱溶媒した。残留物をｎ−ヘキサン
／ジエチルエーテル（95/5）を展開溶媒としてシリカゲ
ルカラムにより精製して目的の４−ｎ−ヘプチルオキシ
−４′−（2,7−オクタジエニルオキシ）トラン0.19gを
得た。Example 1 Synthesis of 4-n-heptyloxy-4 '-(2,7-octadienyloxy) tolan 0.07 g (0.55 mmol) of 2,7-octadien-1-ol,
4-n-heptyloxy-4'-hydroxytolan 0.15
g (0.5 mmol) and 0.16 g of triphenylphosphine were dissolved in 1.5 of dry diethyl ether, and then a solution of 0.12 g of azodicarboxylic acid diisopropyl ester in 0.5 of dry diethyl ether was added dropwise over about 3 minutes. After stirring at room temperature for 3.5 hours, the precipitated triphenylphosphine oxide was filtered off, and the filtrate was desolvated. The residue was purified by a silica gel column using n-hexane / diethyl ether (95/5) as a developing solvent to obtain 0.19 g of the desired 4-n-heptyloxy-4 '-(2,7-octadienyloxy) tolan. Obtained.
融点105.2〜106.1℃ 赤外分光分析の結果、得られた生成物は次の特性吸収
を有しており、目的物であることを確認した。Melting point: 105.2 to 106.1 ° C. As a result of infrared spectroscopy, the obtained product had the following characteristic absorption and was confirmed to be the desired product.
2925cm-1、2855cm-1、2550cm-1、1610cm-1、1515cm-1、
1285cm-1、1245cm-1、1005cm-1、835cm-1、535cm-1 実施例２ ４−ｎ−ヘプチルオキシ−４′−（２−ブチニルオキ
シ）トランの合成 ２−ブチン−１−オール0.05g（0.66mmol）、４−ｎ
−ヘプチルオキシ−４′−ヒドロキシトラン0.18g（0.6
mmol）およびトリフェニルホスフィン0.19gを乾燥ジエ
チルエーテル2.0に溶解した後、アゾジカルボン酸ジイ
ソプロピルエステル0.15gを乾燥ジエチルエーテル0.5と
ともに３分間で滴下した。室温で3.5時間撹拌後、析出
したトリフェニルホスフィンオキシドをろ別し、ろ液を
脱溶媒した。残留物をｎ−ヘキサン／酢酸エチル（95/
5）を展開溶媒としてシリカゲルカラム精製し、目的の
４−ｎ−ヘプチルオキシ−４′−（２−ブチニルオキ
シ）トラン0.15gを得た。2925cm -1 , 2855cm -1 , 2550cm -1 , 1610cm -1 , 1515cm -1 ,
1285 cm -1 , 1245 cm -1 , 1005 cm -1 , 835 cm -1 , 535 cm -1 Example 2 Synthesis of 4-n-heptyloxy-4 '-(2-butynyloxy) tolan 2-butyn-1-ol 0.05 g (0.66 mmol), 4-n
Heptyloxy-4'-hydroxytolan 0.18 g (0.6
mmol) and triphenylphosphine 0.19 g were dissolved in dry diethyl ether 2.0, and azodicarboxylic acid diisopropyl ester 0.15 g was added dropwise with dry diethyl ether 0.5 over 3 minutes. After stirring at room temperature for 3.5 hours, the precipitated triphenylphosphine oxide was filtered off, and the filtrate was desolvated. The residue was purified with n-hexane / ethyl acetate (95 /
Using 5) as a developing solvent, silica gel column purification was performed to obtain 0.15 g of the desired 4-n-heptyloxy-4 '-(2-butynyloxy) tolan.
融点115.0℃ 赤外分光分析の結果、得られた生成物は次の特性吸収
を有しており、目的物であることを確認した。Melting point: 115.0 ° C. As a result of infrared spectroscopy, the obtained product had the following characteristic absorption and was confirmed to be the desired product.
2975cm-1、2850cm-1、2250cm-1、1605cm-1、1515cm-1、
1280cm-1、1240cm-1、1000cm-1、835cm-1、535cm-1 実施例３ ４−ｎ−ヘプチルオキシ−４′−（２−ペンチニルオキ
シ）トランの合成 ２−ペンチン−１−オール0.05g（0.66mmol）、４−
ｎ−ヘプチルオキシ−４′−ヒドロキシトラン0.18g
（0.6mmol）およびトリフェニルホスフィン0.19gを乾燥
ジエチルエーテル2.0に溶解した後、アゾジカルボン酸
ジイソプロピルエステル0.15gを乾燥ジエチルエーテル
0.5とともに３分間で滴下した。室温で４時間撹拌後、
析出したトリフェニルホスフィンオキシドをろ別し、ろ
液を脱溶媒した。残留物をｎ−ヘキサン／エチルエーテ
ル（97/3）を展開溶媒としてシリカゲルカラム精製し、
目的の４−ｎ−ヘプチルオキシ−４′−（２−ペンチニ
ルオキシ）トラン0.08gを得た。 2975cm -1, 2850cm -1, 2250cm -1 , 1605cm -1, 1515cm -1,
1280cm -1, 1240cm -1, 1000cm -1 , 835cm -1, 535cm -1 Example 3 4-n-heptyloxy-4 '- (2-pentynyloxy) Tran Synthesis of 0.05 g (0.66 mmol) of 2-pentyn-1-ol, 4-
0.18 g of n-heptyloxy-4'-hydroxytolan
(0.6 mmol) and 0.19 g of triphenylphosphine were dissolved in 2.0 of dry diethyl ether, and then 0.15 g of diisopropyl azodicarboxylate was added to dry diethyl ether.
It was added dropwise over 3 minutes with 0.5. After stirring at room temperature for 4 hours,
The precipitated triphenylphosphine oxide was filtered off, and the filtrate was desolvated. The residue was purified by a silica gel column using n-hexane / ethyl ether (97/3) as a developing solvent.
0.08 g of desired 4-n-heptyloxy-4 '-(2-pentynyloxy) tolane was obtained.
融点98.7℃ 赤外分光分析の結果、得られた生成物は次の特性吸収
を有しており、目的物であることを確認した。Melting point: 98.7 ° C. As a result of infrared spectroscopy, the obtained product had the following characteristic absorption and was confirmed to be the desired product.
2950cm-1、2875cm-1、2250cm-1、1610cm-1、1520cm-1、
1380cm-1、1245cm-1、1010cm-1、840cm-1、540cm-1 実施例４ ４−ｎ−ヘプチルオキシ−４′−（３−ヘキシニルオキ
シ）トランの合成 ３−ヘキシン−１−オール0.05g（0.55mmol）、４−
ｎ−ヘプチルオキシ−４′−ヒドロキシトラン0.15g
（0.5mmol）およびトリフェニルホスフィン0.16gを乾燥
ジエチルエーテルに溶解した後、アゾジカルボン酸ジイ
ソプロピルエステル0.12gを乾燥ジエチルエーテル0.5と
ともに３分間で滴下した。室温で４時間撹拌後、析出し
たトリフェニルホスフィンオキシドをろ過し、ろ液を脱
溶媒した。残留物をｎ−ヘキサン／エチルエーテル（96
/4）を展開溶媒としてシリカゲルカラム精製し、目的の
４−ｎ−ヘプチルオキシ−４′−（３−ヘキシニルオキ
シ）トラン0.07gを得た。 2950cm -1, 2875cm -1, 2250cm -1 , 1610cm -1, 1520cm -1,
1380cm -1, 1245cm -1, 1010cm -1 , 840cm -1, 540cm -1 Example 4 4-n-heptyloxy-4 '- (3-hexynyloxy) Tran Synthesis of 0.05 g (0.55 mmol) of 3-hexyn-1-ol, 4-
0.15 g of n-heptyloxy-4'-hydroxytolan
(0.5 mmol) and 0.16 g of triphenylphosphine were dissolved in dry diethyl ether, and then 0.12 g of diisopropyl azodicarboxylate was added dropwise together with 0.5 of dry diethyl ether over 3 minutes. After stirring at room temperature for 4 hours, the precipitated triphenylphosphine oxide was filtered, and the filtrate was desolvated. The residue was purified with n-hexane / ethyl ether (96
Using / 4) as a developing solvent, silica gel column purification was performed to obtain 0.07 g of the desired 4-n-heptyloxy-4 '-(3-hexynyloxy) tolan.
融点68.8℃ 赤外分光分析の結果、得られた生成物は次の特性吸収
を有しており、目的物であることを確認した。Melting point: 68.8 ° C. As a result of infrared spectroscopy, the obtained product had the following characteristic absorption and was confirmed to be the desired product.
2950cm-1、2875cm-1、2300cm-1、1615cm-1、1520cm-1、
1520cm-1、1290cm-1、1255cm-1、1050cm-1、845cm-1、8
30cm-1、540cm-1 参考例 本発明になる新規なアルコキシトラン化合物を液晶に
添加することにより、液晶のΔｎを改良することを見る
ために、次の組成になる1:1:1の混合物に10％のトラン
化合物を混合して、そ れぞれのΔｎの変化を測定し、その結果を次に示した。2950cm -1 , 2875cm -1 , 2300cm -1 , 1615cm -1 , 1520cm -1 ,
1520cm -1 , 1290cm -1 , 1255cm -1 , 1050cm -1 , 845cm -1 , 8
By adding 30 cm -1, a novel alkoxy tolans becomes 540 cm -1 Reference Example present invention to a liquid crystal, to see to improve the liquid crystal of [Delta] n, becomes following composition 1: 1: 1 mixture of Mix with 10% tolane compound Each change in Δn was measured, and the results are shown below.
上の結果から明らかなように、本発明になる新規なア
ルコキシトラン化合物は、母液晶のΔｎの値を大きくす
る効果が見られる。 As is clear from the above results, the novel alkoxytolan compound according to the present invention has an effect of increasing the value of Δn of the mother liquid crystal.
Claims (1)
ラン化合物。 （式中、Ｒは炭素原子数１〜18のアルキル基を示し、
Ｒ′は炭素原子数３〜17のアルキニル基またはアルカジ
エニル基を示す。）1. An alkoxytolan compound represented by the following general formula (I). (Wherein, R represents an alkyl group having 1 to 18 carbon atoms,
R 'represents an alkynyl group or an alkadienyl group having 3 to 17 carbon atoms. )
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1026373A JP2701064B2 (en) | 1989-02-03 | 1989-02-03 | Alkoxy tolan compounds |
| US07/397,036 US5047169A (en) | 1988-09-16 | 1989-08-21 | Tolane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1026373A JP2701064B2 (en) | 1989-02-03 | 1989-02-03 | Alkoxy tolan compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02207056A JPH02207056A (en) | 1990-08-16 |
| JP2701064B2 true JP2701064B2 (en) | 1998-01-21 |
Family
ID=12191710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1026373A Expired - Fee Related JP2701064B2 (en) | 1988-09-16 | 1989-02-03 | Alkoxy tolan compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2701064B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047169A (en) * | 1988-09-16 | 1991-09-10 | Adeka Argus Chemical Co., Ltd. | Tolane compound |
| IL100643A (en) * | 1991-01-25 | 1996-10-31 | Nippon Kayaku Kk | Hydrazine derivatives and pesticidal compositions comprising such derivatives as effective component |
| US5833879A (en) * | 1995-02-15 | 1998-11-10 | Chisso Corporation | Liquid crystalline alkynyltolan compound, liquid crystal composition and liquid crystal display element |
-
1989
- 1989-02-03 JP JP1026373A patent/JP2701064B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02207056A (en) | 1990-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0126469B1 (en) | Optically active 1,3-dioxolane derivatives containing a mesogene group in position 4. method for their preparation and theiruse as doping agents in liouid-crystal mixtures | |
| KR100821844B1 (en) | Liquid crystal composition comprising novel silicon containing compounds and liquid crystal display device using the same | |
| JP2701064B2 (en) | Alkoxy tolan compounds | |
| KR920009973B1 (en) | Process for preparing 4-substituted phenyl crotyl ether derivative | |
| US5047169A (en) | Tolane compound | |
| EP0170082A2 (en) | Liquid crystalline isothiocyanates with a dioxane ring and liquid crystalline admixtures containing the same | |
| JP2573038B2 (en) | Alkynyl oxytran compounds | |
| JP2739082B2 (en) | Isopentenyl oxytran compound | |
| JPS6228137B2 (en) | ||
| JP3763495B2 (en) | Pyridinium-type ionic compound derivative, its production method and liquid crystal substance | |
| US4826979A (en) | Liquid crystal compound | |
| JP2691766B2 (en) | Alkenoxy cyanobiphenyl compound | |
| KR0166379B1 (en) | Phenylcyclodioxane derivatives having an ether bond | |
| EP0198714B1 (en) | Liquid cristalline compositions containing cyclohexylcyclohexene derivatives, and their use | |
| JP2748025B2 (en) | Alkynyloxyphenylcyclohexane compound | |
| JP2558803B2 (en) | Optically active bisaryl compounds | |
| JP4627576B2 (en) | Phenylacetylene compound having fluorine-substituted alkyl group or alkoxy group in its skeleton, its intermediate, its production method, liquid crystal composition containing it, and liquid crystal device using the same | |
| JP2830333B2 (en) | Ether-based tricyclic liquid crystal compound | |
| CN113004904B (en) | Liquid crystal compound containing cyclohexene structure and preparation method thereof | |
| US5462695A (en) | Chiral liquid crystal materials as dopant for ferroelectric liquid crystal compositions | |
| US5166391A (en) | Optically-active aliphatic α-halogen substituted carboxylic acid 4'-(alkoxybenzyloxy)biphenyl thioester compounds | |
| US5210267A (en) | Optically-active aliphatic β-halogen substituted carboxylic acid 4'-(4-alkoxybenzyloxy)biphenyl thioester compounds and process for the preparation thereof | |
| JP3579912B2 (en) | Benzene derivative and liquid crystal composition | |
| JPS60204769A (en) | Halogenopyrimidine derivative | |
| JP4721536B2 (en) | Fluorocarboxylic acid phenyl ester compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |