JP2801627B2 - Organic liquid crystal compounds - Google Patents
Organic liquid crystal compoundsInfo
- Publication number
- JP2801627B2 JP2801627B2 JP1050059A JP5005989A JP2801627B2 JP 2801627 B2 JP2801627 B2 JP 2801627B2 JP 1050059 A JP1050059 A JP 1050059A JP 5005989 A JP5005989 A JP 5005989A JP 2801627 B2 JP2801627 B2 JP 2801627B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- organic liquid
- present
- crystal compounds
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- 230000006399 behavior Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000015654 memory Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- UYRPOMMBPQHVMN-UHFFFAOYSA-N 1,4-bis(chloromethyl)-2,5-dimethylbenzene Chemical compound CC1=CC(CCl)=C(C)C=C1CCl UYRPOMMBPQHVMN-UHFFFAOYSA-N 0.000 description 1
- MNHWRUCVFATHDL-UHFFFAOYSA-N 2-methylterephthalaldehyde Chemical compound CC1=CC(C=O)=CC=C1C=O MNHWRUCVFATHDL-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- KDEDDPRZIDYFOB-UHFFFAOYSA-N n-methyl-n-phenylnitramide Chemical compound [O-][N+](=O)N(C)C1=CC=CC=C1 KDEDDPRZIDYFOB-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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】 ［発明の目的］ （産業上の利用分野） 本発明は、新規で有用な共役系有機液晶化合物に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Object of the Invention] (Industrial application field) The present invention relates to a novel and useful conjugated organic liquid crystal compound.
（従来の技術） 液晶化合物は、例えばネマチック液晶化合物の電気光
学効果を利用した表示素子に広く利用されている。(Prior Art) A liquid crystal compound is widely used for a display element utilizing an electro-optic effect of a nematic liquid crystal compound, for example.
また最近、高速の応答速度を有する強誘電性液晶の研
究も盛んである。Recently, studies on ferroelectric liquid crystals having a high response speed have been actively conducted.
一方、共役系の有機化合物、例えばメチルーニトロア
ニリン等が高い非線形光学効果を有することが明らかに
なって以来、光機能材料としての新しい共役系有機化合
物の開発研究も盛んである。On the other hand, since it has been found that conjugated organic compounds, for example, methyl-nitroaniline and the like, have a high nonlinear optical effect, research and development of new conjugated organic compounds as optical functional materials has been active.
本発明は、液晶挙動を有し、かつ光機能材料として有
用な新規な共役系の有機化合物を提供することを目的と
するものである。An object of the present invention is to provide a novel conjugated organic compound having a liquid crystal behavior and useful as an optical functional material.
［発明の構成］ （課題を解決するための手段） 本発明者らは、共役系有機液晶化合物について鋭意研
究した結果、特定の構造を有する有機化合物が、蛍光発
光等の発光特性が付与され、また適当な温度域で液晶挙
動を示す有用な共役系有機液晶化合物となることを見出
し、本発明に到達した。[Constitution of the Invention] (Means for Solving the Problems) The present inventors have conducted intensive studies on conjugated organic liquid crystal compounds, and as a result, an organic compound having a specific structure is provided with emission characteristics such as fluorescence emission. In addition, they have found that they are useful conjugated organic liquid crystal compounds that exhibit liquid crystal behavior in an appropriate temperature range, and have reached the present invention.
すなわち、本発明の液晶化合物は、次式 ［式中、ＲおよびＲ′は、 （式中、Ｘはシアノ基またはニトロ基を表す）で示され
る基を表す。That is, the liquid crystal compound of the present invention has the following formula: Wherein R and R ′ are (Wherein, X represents a cyano group or a nitro group).
Ｒ″およびＲはメチル基を表す］で示される構造を
有する液晶化合物である。R ″ and R each represent a methyl group].
式（Ｉ）において、炭素−炭素二重結合におけるトラ
ンス型結合の平均含有率（Ct）は、本発明の共役系有機
液晶化合物の液晶形成機能、熱相転移挙動に影響し、Ct
は好ましくは60％以上、さらに好ましくは80％以上、と
くに好ましくは100％である。In formula (I), a carbon - average content of trans bonds in carbon-carbon double bond (C t), the liquid crystal forming function of conjugated organic liquid crystal compound of the present invention, affects the thermal phase transition behavior, C t
Is preferably 60% or more, more preferably 80% or more, particularly preferably 100%.
上述した本発明の共役系有機液晶化合物は、例えば下
記反応式のルートで合成される。The conjugated organic liquid crystal compound of the present invention described above is synthesized, for example, by the route of the following reaction formula.
（発明の効果） 本発明の有機液晶化合物は、固体相から中間相への転
移温度以上で液晶相を示す。 (Effect of the Invention) The organic liquid crystal compound of the present invention exhibits a liquid crystal phase at a transition temperature from a solid phase to an intermediate phase or higher.
また、本発明の有機液晶化合物はその共役系に起因す
る蛍光発光特性を有する。Further, the organic liquid crystal compound of the present invention has a fluorescent light emitting characteristic due to its conjugated system.
本発明の有機液晶化合物は、液晶相域で電場、磁場に
より分子配向すること、またこの分子配向を固定相で固
定できることから、情報のメモリーおよび表示に応用す
ることができる。特に蛍光発光機能を利用した表示素子
として応用できる。The organic liquid crystal compound of the present invention can be applied to information memory and display because it can be molecularly oriented by an electric field and a magnetic field in a liquid crystal phase region and this molecular orientation can be fixed by a stationary phase. In particular, it can be applied as a display element utilizing a fluorescent light emitting function.
さらには、液晶相域で電場、磁場により共役系分子を
配向させて冷却させることで共役系の配向を固定するこ
とができることから高効率な非線形光学材料として応用
することもできる。Furthermore, since the orientation of the conjugated system can be fixed by orienting and cooling the conjugated system molecules by an electric or magnetic field in the liquid crystal phase region, it can be applied as a highly efficient nonlinear optical material.
また、本発明の有機液晶化合物を高分子化合物、とく
に有機高分子に分散させて複合材料として利用すること
ができる。Further, the organic liquid crystal compound of the present invention can be used as a composite material by dispersing it in a polymer compound, particularly an organic polymer.
有機高分子としては、ポリスチレン、ポリメチルメタ
クリレート等のポリアクリレート、ポリアルキルアクリ
ルレート、ポリエチレンテレフタレート、ポリカーボネ
ート等があげられる。Examples of the organic polymer include polyacrylate such as polystyrene and polymethyl methacrylate, polyalkyl acrylate, polyethylene terephthalate, and polycarbonate.
これらの有機高分子に複合された形で、本発明の液晶
化合物の液晶挙動および蛍光発光特性を利用した情報メ
モリー、表示、非線形光学デバイス等に応用することが
できる。When compounded with these organic polymers, they can be applied to information memories, displays, non-linear optical devices and the like utilizing the liquid crystal behavior and fluorescence emission characteristics of the liquid crystal compound of the present invention.
以下、実施例をあげて本発明を具体的に説明する。 Hereinafter, the present invention will be described specifically with reference to examples.
実施例１ 下記構造式を有する有機液晶化合物を合成した。Example 1 An organic liquid crystal compound having the following structural formula was synthesized.
すなわち、2,5−ジメチル−1,4−ジクロロメチルベン
ゼン25gとトリフェニルホスフィン80gをジメチルホルム
アミド300mlに溶解し、153℃で３時間反応させた。 That is, 25 g of 2,5-dimethyl-1,4-dichloromethylbenzene and 80 g of triphenylphosphine were dissolved in 300 ml of dimethylformamide and reacted at 153 ° C. for 3 hours.
反応物を室温に冷却した後、ジメチルホルムアミドで
２回、次いで、ジエチルエーテルで２回洗浄後、減圧乾
燥して を得た。The reaction was cooled to room temperature, washed twice with dimethylformamide, then twice with diethyl ether, and dried under reduced pressure. I got
この化合物（Ａ）19gをメタノールとジメチルホルム
アミド等量混合物200mlに溶解し、そこにテレフタルア
ルデヒド酸メチル7.7gをジメチルホルムアミド50mlに溶
解した溶液とナトリウム1.1gをメタノール20mlに溶解し
た溶液を同時に滴下し、室温で10時間反応させた。19 g of this compound (A) was dissolved in 200 ml of an equal mixture of methanol and dimethylformamide, and a solution of 7.7 g of methyl terephthalaldehyde in 50 ml of dimethylformamide and a solution of 1.1 g of sodium dissolved in 20 ml of methanol were simultaneously added dropwise. The reaction was performed at room temperature for 10 hours.
析出物を別し、メタノールで再結晶して、次式 で示される化合物を得た。Separate the precipitate, recrystallize with methanol, Was obtained.
この化合物（Ｂ）6.8gとＮ−ブロモコハク酸イミド6g
をベンゼン700mlに溶解し、過酸化ベンゾイル0.5gを加
えて、80.5℃で10時間反応させた。6.8 g of this compound (B) and 6 g of N-bromosuccinimide
Was dissolved in benzene (700 ml), benzoyl peroxide (0.5 g) was added, and the mixture was reacted at 80.5 ° C. for 10 hours.
析出した固体を別し、水で洗浄後、乾燥して、次式 で示される化合物を得た。The precipitated solid is separated, washed with water, dried, and Was obtained.
この化合物（Ｃ）6gとトリフェニルホスフィン6gとを
ジメチルホルムアミド50mlに溶解し、153℃で１時間反
応させた。6 g of this compound (C) and 6 g of triphenylphosphine were dissolved in 50 ml of dimethylformamide and reacted at 153 ° C. for 1 hour.
反応物を室温に冷却した後、ジメチルホルムアミドで
２回、次いでジエチルエーテルで２回洗浄後、減圧乾燥
して を得た。The reaction was cooled to room temperature, washed twice with dimethylformamide, then twice with diethyl ether, and dried under reduced pressure. I got
化合物（Ｄ）9gをメタノール１とDMF100mlの混合液
に溶解し、そこに、Ｐ−シアノベンズアルデヒド2.5gを
DMF 100mlに溶解した溶液とナトリウム0.37gを10mlのメ
タノールに溶解した溶液を同時に滴下し、室温で12時間
撹拌した。析出物を別し、溶媒を留去し、残留物をメ
タノールで再結晶して本発明の目的化合物を得た。9 g of compound (D) was dissolved in a mixture of methanol 1 and DMF 100 ml, and 2.5 g of P-cyanobenzaldehyde was added thereto.
A solution of 100 ml of DMF and a solution of 0.37 g of sodium dissolved in 10 ml of methanol were simultaneously added dropwise, and the mixture was stirred at room temperature for 12 hours. The precipitate was separated, the solvent was distilled off, and the residue was recrystallized from methanol to obtain the target compound of the present invention.
この化合物（Ｅ）は280℃以上318℃未満で液晶相を示
した。 This compound (E) showed a liquid crystal phase at 280 ° C or higher and lower than 318 ° C.
この化合物（Ｅ）の蛍光スペクトルを図１に示した。 FIG. 1 shows the fluorescence spectrum of the compound (E).
実施例２ 実施例１におけるＰ−シアノベンズアルデヒドの代り
にＰ−ニトロベンズアルデヒドを用いて、 の化合物を合成した。Example 2 Using P-nitrobenzaldehyde instead of P-cyanobenzaldehyde in Example 1, Was synthesized.
この化合物は263℃以上323℃未満で液晶相を示した。 This compound showed a liquid crystal phase at 263 ° C. or higher and lower than 323 ° C.
この化合物の蛍光スペクトルを図２に示した。 The fluorescence spectrum of this compound is shown in FIG.
図１および２は、それぞれ実施例１および２の合物の蛍
光スペクトル図である。1 and 2 are fluorescence spectrum diagrams of the compounds of Examples 1 and 2, respectively.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 氏家 誠司 千葉県松戸市緑ケ丘１―153 クリーン ハイツ103 (72)発明者 宮林 光孝 三重県四日市市東邦町１番地 三菱油化 株式会社新素技研究所内 (56)参考文献 特開 平２−229822（ＪＰ，Ａ) 特開 昭61−227546（ＪＰ，Ａ) (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 63/00 C07C 69/00 C07C 205/57 C07C 255/57 C09K 19/16 C09K 19/32 ＣＡ（ＳＴＮ)──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Seiji Ujiie 1-153 Midorigaoka, Matsudo-shi, Chiba Clean Heights 103 (72) Inventor Mitsutaka Miyabayashi 1 Tohocho, Yokkaichi-shi, Mie Mitsubishi Oil Chemicals Co., Ltd. (56) References JP-A-2-229822 (JP, A) JP-A-61-227546 (JP, A) (58) Fields investigated (Int. Cl. 6 , DB name) C07C 63/00 C07C 69 / 00 C07C 205/57 C07C 255/57 C09K 19/16 C09K 19/32 CA (STN)
Claims (1)
る基を表し、Ｒ″およびＲはメチル基を表す。1. A liquid crystal compound having the following structural formula. Wherein R and R ′ are (Wherein X represents a cyano group or a nitro group), and R ″ and R represent a methyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1050059A JP2801627B2 (en) | 1989-03-03 | 1989-03-03 | Organic liquid crystal compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1050059A JP2801627B2 (en) | 1989-03-03 | 1989-03-03 | Organic liquid crystal compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02229136A JPH02229136A (en) | 1990-09-11 |
| JP2801627B2 true JP2801627B2 (en) | 1998-09-21 |
Family
ID=12848429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1050059A Expired - Lifetime JP2801627B2 (en) | 1989-03-03 | 1989-03-03 | Organic liquid crystal compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2801627B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2478711C (en) * | 2002-03-26 | 2010-11-09 | Council Of Scientific And Industrial Research | Non-visualized permanent information recording substrate for use as security label for authentication |
| AU2010336009B2 (en) | 2009-12-21 | 2014-04-03 | Boulos & Cooper Pharmaceuticals Pty Ltd | Antimicrobial compounds |
-
1989
- 1989-03-03 JP JP1050059A patent/JP2801627B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02229136A (en) | 1990-09-11 |
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