JPS6360972A - Pyrimidine compound - Google Patents
Pyrimidine compoundInfo
- Publication number
- JPS6360972A JPS6360972A JP20282186A JP20282186A JPS6360972A JP S6360972 A JPS6360972 A JP S6360972A JP 20282186 A JP20282186 A JP 20282186A JP 20282186 A JP20282186 A JP 20282186A JP S6360972 A JPS6360972 A JP S6360972A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- expressed
- carbon atoms
- 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
- -1 Pyrimidine compound Chemical class 0.000 title claims abstract description 11
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 55
- 239000000463 material Substances 0.000 abstract description 9
- 239000003054 catalyst Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000007269 dehydrobromination reaction Methods 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract 2
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- SJXANNYEGSIUSX-UHFFFAOYSA-N CCCCCC1=CN=C(C)N=C1 Chemical compound CCCCCC1=CN=C(C)N=C1 SJXANNYEGSIUSX-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001553014 Myrsine salicina Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、新規なピリミジン化合物および該化合物を含
有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel pyrimidine compound and a liquid crystal composition containing the compound.
液晶物質およびその組成物は、その液晶相（：おける誘
電率の異方性（Δ８と略記する）および光の屈折率の異
方性（Δｎと略記する）を利用して、種々の表示装置に
利用されている。Liquid crystal substances and compositions thereof can be used in various display devices by utilizing the anisotropy of the dielectric constant (abbreviated as Δ8) and the anisotropy of the refractive index of light (abbreviated as Δn) in the liquid crystal phase (:). It is used for.
液晶表示方式には、応用される電気光学効果に対応して
、電界制御複屈折型（ＥＣＢ型）、動的散乱型（Ｄａ型
）、ねじれネマチック型（ＴＮ型）、スーパーツイスト
ｇＬ屈折型（ＳＢＥ型）、ゲスト・ホスト型など種々の
方式があり、それぞれの方式により使用される液晶材料
Ｃ：要求される性質も異なる。Depending on the applied electro-optical effect, liquid crystal display methods include electric field controlled birefringence type (ECB type), dynamic scattering type (Da type), twisted nematic type (TN type), and super twisted gL refraction type ( There are various methods such as SBE type) and guest-host type, and each method requires different properties of the liquid crystal material C used.
これらの液晶材料は単独の化合物では、その緒特性、例
えば、液晶温度範囲、動作電圧、応答性能等において実
用的な使用に耐える物はなく、実用的には数種の液晶化
合物あるいは非液晶化合物を混合して使用（＝耐えうる
材料を得ている。又液晶材料は、水分、熱、光、″４気
、空気等に対しても安定である必要がある。These liquid crystal materials are not single compounds that can withstand practical use in terms of their characteristics, such as liquid crystal temperature range, operating voltage, response performance, etc., and for practical purposes, several types of liquid crystal compounds or non-liquid crystal compounds are needed. A liquid crystal material must be stable against moisture, heat, light, air, air, etc.
Ｔ、 Ｎ Ｗセルに於ては、パウアーによってＭｏｌ。In the T, NW cell, Mol by Pauer.
Ｃｒｙｓｔ、Ｌｉｑ、Ｃｒｙｓｔ、 ６３，４３ （１
９８１）に報告されるように、表示セルの外観を損なう
原因である干渉縞の発生を防止する為にセルに充填され
る液晶材料の６口とセル厚さｄ（μ溝）の積をある特定
の値Ｃ：設定する必要がある。実用的に使用されている
液晶表示セルでは、Δｎ−ｄの値が０．５、輌１．０．
１．６又は２．２の何れかＣ：設定されている。さらに
、Δｎ−ｄが特定の値の場合に、Δｎが大きいとｄを小
さくすることができ、レスポンスが向上する。また、ｄ
が小さいと同じ印加重圧でも電界強度が大きくなり、低
７ｉ圧駆動ができる。また、Δｎ−ｄの値が太きいと表
示セルのコントラストが良くなる。このため、Δｎが大
きく他の緒特性が程良くバランスした液晶性化合物が必
要とされる。Cryst, Liq, Cryst, 63,43 (1
As reported in 981), in order to prevent the occurrence of interference fringes that impair the appearance of display cells, the product of the 6 holes of liquid crystal material filled in the cell and the cell thickness d (μ groove) is calculated as Specific value C: Must be set. In a liquid crystal display cell that is practically used, the value of Δn-d is 0.5, 1.0.
Either 1.6 or 2.2 C: Set. Furthermore, when Δn−d is a specific value, if Δn is large, d can be made small, and the response is improved. Also, d
When is small, the electric field strength becomes large even with the same applied pressure, and low 7i pressure driving is possible. Further, when the value of Δn-d is large, the contrast of the display cell becomes better. Therefore, a liquid crystal compound with a large Δn and a good balance of other properties is required.
本発明の目的は、液晶組成物の成分（＝用いること（二
より、表示素子の緒特性を向上出来る化合物及び該化合
物を含有する液晶組成物を提供することである。An object of the present invention is to provide a compound that can improve the performance characteristics of a display element as a component of a liquid crystal composition, and a liquid crystal composition containing the compound.
本発明は、一般式
（式中Ｘは、炭素数１〜１２のアルキル基、炭素数１〜
１２のアルコキン基、フッ素またはシアノ基を示し、Ｙ
は−Ｃ）Ｉ−ＣＨ−または−ＱＥＣ−を示し・Ｒは炭素
数１〜１２のアルキル基または炭素数１〜１２のアルコ
キン基を示す。）
で表わされるピリミジン化合物および該化合物を含有す
る液晶組成物である。The present invention is based on the general formula (wherein X is an alkyl group having 1 to 12 carbon atoms,
12 alkoxy group, fluorine or cyano group, Y
represents -C)I-CH- or -QEC-, and R represents an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. ) A pyrimidine compound represented by: and a liquid crystal composition containing the compound.
本発明の化合物は、Δｎが大きく、Δεが正なる液晶性
化合物である。ここで液晶性化合物とは通常液晶相を示
す化合物のはかＣ二、通常液晶相を示さないが、他の液
晶化合物に溶解した烏合に液晶挙動の成る面に有効に作
用する化合物を意味する。また本発明の化合物にはネマ
チック相を有する化合物が存在する。The compound of the present invention is a liquid crystalline compound having a large Δn and a positive Δε. Here, the term "liquid crystal compound" refers to a compound that normally exhibits a liquid crystal phase, or a compound that does not normally exhibit a liquid crystal phase, but which effectively acts on the aspect of liquid crystal behavior when dissolved in another liquid crystal compound. . Further, some of the compounds of the present invention have a nematic phase.
（１）式でＹが−Ｃ））＝ＣＨ−である化合物としては
トランス型の物が好ましい。このトランス型エチレン誘
導体（：はΔｎが大舞いネマチック液晶化合物が多い。The compound in which Y is -C))=CH- in formula (1) is preferably a trans-type compound. This trans-type ethylene derivative (:) has a large Δn and is often a nematic liquid crystal compound.
本発明のトランス型エチレン誘導体としては、（１）式
でＸおよびＲが炭素数２〜９のアルキル基もしくはアル
コキン基である化合物が好ましく、Ｘおよび凡の炭素数
の合計が４〜１６である鎖長の末端基をもつ化合物が好
ましい。As the trans-type ethylene derivative of the present invention, a compound in which X and R are an alkyl group or an alkoxy group having 2 to 9 carbon atoms in the formula (1) is preferable, and the total number of carbon atoms in X and R is 4 to 16. Compounds with long chain end groups are preferred.
（１）式でＹが−×−である化合物（：は潜在的に液晶
性を何する物が多い。これらの化合物は液晶化合物また
は液晶混合物に添加して、得られる組成物の△ｎを増大
するのＣ：有用である。In formula (1), Y is -x- in many cases (: has a potential effect on liquid crystallinity. These compounds can be added to a liquid crystal compound or liquid crystal mixture to change the △n of the resulting composition. Increase C: Useful.
本発明の化合物は表示用液晶材料に要求される、水分、
空気、熱、光、Ｌ気等に対する安定性も備えている。さ
らに、本発明の化合物は、他の液晶性化合物例えば、エ
ステル系、ンッフ塩素系、アゾキン系、ビフェニル系、
ンクロへキチン系、ピリジン系、ピリミジン系、ジ万キ
サン系等の液晶性化合物との相溶性か：ぐれているので
、それ等の化合物または、それらの７昆合物とｔ昆合す
ることにより・各種の表示素子用に適した液晶組成物を
＋１ｔ 成することができる。例えば、ＴＮ表示素子用
液晶組成物の成分として添加すること（二より、該液晶
組成物の△εやＮＩ点をさほど低−ドさせることなくΔ
ｎ゛を増大させる効果がある。The compound of the present invention has the ability to reduce moisture and
It also has stability against air, heat, light, L air, etc. Furthermore, the compound of the present invention can be used with other liquid crystalline compounds such as ester-based, nuff-chlorine-based, azoquine-based, biphenyl-based,
Compatibility with liquid crystalline compounds such as cyclohexane, pyridine, pyrimidine, dimoxane, etc.: They are not compatible, so by merging with such compounds or their seven combinations,・Liquid crystal compositions suitable for various display devices can be produced. For example, it can be added as a component of a liquid crystal composition for TN display elements (secondarily, Δε and NI points of the liquid crystal composition can be added without lowering too much).
This has the effect of increasing n.
本発明の化合物は例えば次のようにして合成できる。The compound of the present invention can be synthesized, for example, as follows.
第１段
（１） （１） （ＩＴＩ
＄２段
（Ｖ） （ｆｆ）
（Ｖｌ）第３段
（Ｍｌ （Ｗ）
第４段
（■） （（資）（式中
Ｘは、炭素数１−１２のアルキル基・炭素数１〜１２の
アルコキン基、フッ素またはンアノ基を示し、Ｒは炭素
数１〜１２のアルキル基または炭素数１〜１２のアルコ
キン基を示す。）
まず、アセトアミジン塩酸塩（ｌとα−置換−β−ジメ
チルアミノアクロレイン（菫）とを塩基触媒（たとえば
、金属アルコラード、水酸化ナトリウム、１，８−ジア
ザピンクロ（５，４，○〕−７−ウンデセンなど）の存
在下に縮合環化反応を行ない５−置換−２−メブールビ
リミジン（バ）を得る。1st paragraph (1) (1) (ITI
$2 step (V) (ff)
(Vl) Third stage (Ml (W)
4th stage (■) ((capital) (wherein, First, acetamidine hydrochloride (1) and α-substituted-β-dimethylaminoacrolein (violet) are combined with a base catalyst (e.g., metal alcoholade, sodium hydroxide, 1 , 8-diazapinechlor(5,4,○]-7-undecene, etc.) to obtain 5-substituted-2-mebourpyrimidine (b).
次Ｃ二、化合物（Ｉｆ）とｐ−置換−ベンチアルデヒド
（Ｖｌを縮合剤（たとえば、塩化亜鉛、無水酢酸等）の
存在下（：、脱水縮合反応を行ないピリミジン化合物（
ＩＦ）を得る。この化合物（■）は、本発明の化合物の
一つである。Next, in the presence of a condensing agent (e.g., zinc chloride, acetic anhydride, etc.), compound (If) and p-substituted-bencialdehyde (Vl) undergo a dehydration condensation reaction to form a pyrimidine compound (
IF). This compound (■) is one of the compounds of the present invention.
さらに、化合物（町に臭素を付加して、ジブロモ化合物
（ＩＩ）を得る。Furthermore, bromine is added to the compound to obtain dibromo compound (II).
最後に、化合物（■）を塩基触媒（たとえば、１．８−
ジアザピンクロ（５，４，０） −７−ウンデセン、１
，５−ジアザピンクロ（４，３，０）−５−ノネン、カ
リウム−ｔｅｒｔ−ブトキシド等）の存在下（−脱臭化
水素反応を行ないピリミジン化合物（■）を得ることが
できる。Finally, compound (■) is treated with a base catalyst (for example, 1.8-
Diazapinculo(5,4,0)-7-undecene, 1
, 5-diazapinechloro(4,3,0)-5-nonene, potassium-tert-butoxide, etc.) (-dehydrobromination reaction can be carried out to obtain a pyrimidine compound (■).
本発明の液晶組成物は第一の成分として前記した（＋＞
式で表わされるピリミジン化合物を少くとも一つ含有し
、第二の成分として既知のネマチック液晶化合物を少く
とも一つ含有する。The liquid crystal composition of the present invention is as described above as the first component (+>
It contains at least one pyrimidine compound represented by the formula and at least one known nematic liquid crystal compound as a second component.
本発明の液晶組成物の第二の成分である液晶物質として
は、前記したエステル系、ンッフ塩基系、ビフェニル系
、ンクロヘキチン系、ピリジン系、ピリミジン系、ジオ
キサン系等の液晶化合物または混合物を適当Ｃユ用いる
ことができる。As the liquid crystal substance which is the second component of the liquid crystal composition of the present invention, liquid crystal compounds or mixtures of the above-mentioned esters, Nuff bases, biphenyls, nclohexines, pyridines, pyrimidines, dioxanes, etc. can be used. You can use it.
以下に、実施例（二より、本発明の詳細な説明するが、
本発明は、これらの実施例（：限られるものではない。The following is a detailed explanation of the present invention from Examples (Second).
The present invention is not limited to these examples.
実施例１
（第１段）
無水メタノール１．５／（−ナトリウムメチラート１７
０ ｆ （３，１ｍｏｌりを溶解した溶液ニアセトアミ
ジン塩酸塩２０ｏ ｔ （２，１ｍｏｅ ）及びα−ベ
ンチルーβ−ジメチルアミノアクロレイン３５４ ｔ
（２，１ｍｏｚ）を加え攪拌しながら３時間加熱ａｊ島
した後に、メタノールを留去した。Example 1 (1st stage) Anhydrous methanol 1.5/(-sodium methylate 17
0 f (a solution containing 3.1 mol of niacetamidine hydrochloride 20 t (2.1 moe) and α-benzene-β-dimethylaminoacrolein 354 t
(2.1 moz) was added and heated for 3 hours while stirring, and then methanol was distilled off.
反応残渣に水５００ｍ／とトルエン５００ｒｎｌｌ！を
加え生成物をトルエン層に抽出し、抽出液を水洗し、そ
の後（：トルエンを留去して、残渣を減圧下に蒸留（ｂ
ｐ、 ９０℃／ ２，５１ｔｒｌ−１ｆ ） Ｌ テ、
２−メチル−５−ペンチルピリミジン２６３Ｆ（１，６
ｍｏＩりを得た。Add 500ml of water and 500ml of toluene to the reaction residue! The product was extracted into a toluene layer, the extract was washed with water, and then the toluene was distilled off and the residue was distilled under reduced pressure (b
p, 90℃/2,51trl-1f) L Te,
2-Methyl-5-pentylpyrimidine 263F (1,6
MoI was obtained.
（第２段）
２−メチル−５−ペンチルピリミジン５０ｆ（０，３０
ｍａｔ ）とｐ−ブトキンベンズアルデヒド６２ｆ（０
，３５ｍｏｐ ）及び塩化亜鉛６２１（０，４５ｍａｔ
）を窒素気流下にて、撹拌しながら３時間１８０℃の
マントルヒーターで刃口熱した後に・冷却してトルエン
１００ ｍｌ ト水３００ゴを加え生成物をトルエン層
に抽出し、抽出液を２Ｎ−・水酸化ナトリウム水溶液２
００ｍ／で３回洗浄後さらに水層が中性になるまで水で
洗浄した。このトルエン溶液を乾燥後、減圧１縮して残
渣をエタノールで再結晶精製して、下記化合物３２ｆ（
０，１０ｍｏ／）を得た。(Second stage) 2-methyl-5-pentylpyrimidine 50f (0,30
mat ) and p-butquine benzaldehyde 62f (0
, 35mop) and zinc chloride 621 (0,45mat
) was heated with a mantle heater at 180°C for 3 hours while stirring under a nitrogen stream, then cooled, and 100 ml of toluene and 300 ml of water were added to extract the product into a toluene layer, and the extract was diluted with 2N -・Sodium hydroxide aqueous solution 2
After washing three times at 00 m/g, the sample was further washed with water until the aqueous layer became neutral. After drying this toluene solution, it was condensed under reduced pressure and the residue was purified by recrystallization with ethanol to obtain the following compound 32f (
0.10 mo/) was obtained.
ＣＮ点７６℃、ＮＩ点１０１℃
またこの化合物の元素分析値は次の如く理論値とよく一
致した。The CN point was 76°C and the NI point was 101°C.The elemental analysis values of this compound were in good agreement with the theoretical values as shown below.
実施例２
（第３段）
実施例１で合成した化合物２５ ｆ （０，０７７ｍｏ
／ ）を塩化メチレン２００ｄＣ溶解し、氷水浴冷却下
（−臭素１２．５ ｆ （０，０７８ｍｏ／ ）を塩化
メチレン５ｏ−に溶解した溶液を３０分間で滴下した後
（：室温で３時間攪拌後Ｃ：、反応液を減圧濃縮した。Example 2 (3rd stage) Compound 25 f (0,077 mo
) was dissolved in 200 dC of methylene chloride, and a solution of 12.5 f (0,078 mo/) of bromine dissolved in 5 o of methylene chloride was added dropwise over 30 minutes under cooling in an ice water bath (after stirring at room temperature for 3 hours). C: The reaction solution was concentrated under reduced pressure.
この残渣を塩化メチレンとヘプタン（１：２）の混合溶
媒Ｃ：て再結晶精製して、下記化合物３１ｆ （０，０
６４ｍｏ！ ）を得た。This residue was recrystallized and purified using a mixed solvent C of methylene chloride and heptane (1:2) to obtain the following compound 31f (0,0
64mo! ) was obtained.
（第４段）
この化合物１５ ｔ （０，０３１ｍｏ／ ）をテトラ
ヒドロフラン１５０−に溶解し、氷水浴で冷却し、窒素
気流下ｇ二て攪拌しながら、カリウム−ｔｅｒｔ−ブト
キシド８．７ ｔ （０，０７７ｍａ！ ）を徐々に加
えた後（＝、氷水浴を４０℃まで加熱し、４０℃で５時
開攪拌した。この反応液Ｃ）ルエン２００−及び水５０
０−を加え生成物をトルエン層（：抽出し、抽出液を水
洗し、このトルエン溶液を乾燥し、減圧濃縮して、残渣
をエタノールで再結晶精製して、下記化合物６ｆ（０，
０１９ｍｏ／ ）を得た。(Fourth stage) 15 t (0,031 mo/) of this compound was dissolved in 150 mol of tetrahydrofuran, cooled in an ice-water bath, and stirred under a nitrogen stream while 8.7 t (0,031 mo/) of potassium tert-butoxide was dissolved in , 077 ma!) was gradually added (=, the ice-water bath was heated to 40°C, and the mixture was stirred at 40°C for 5 hours. This reaction solution C) contained 200% of toluene and 50% of water.
0- was added to extract the product from the toluene layer (:), the extract was washed with water, the toluene solution was dried and concentrated under reduced pressure, and the residue was purified by recrystallization with ethanol to obtain the following compound 6f (0,
019mo/ ) was obtained.
ＣＩ点９３℃、ＮＩ点８５℃ （七／トロσソクノまた
この化合物の元素分析値は次の如く理論値とよく一致し
た。CI point: 93°C, NI point: 85°C (7/Toro σ Sokno) Also, the elemental analysis values of this compound were in good agreement with the theoretical values as shown below.
実施例３〜２５
実施例１および実施例２に準じた方法で合成した化合物
とその物性値を実施例１及び実施例２の結果とともに表
Ｉ Ｃ示す。表１の相転移点の欄Ｉ：於いてＣは結晶相
・Ｎはネマチック相・Ｉは等方性液体相を示し、（）は
モノトロピック転移であることを示す。またη２゜は２
０℃Ｃ：於ける粘度を示す。表１（二於けるΔｎ、Δε
およびη２゜は、後記の実施例２６（使用例）に準じて
調製した組成物の特性値から外挿法により求めた値であ
る。Examples 3 to 25 Compounds synthesized by methods similar to Examples 1 and 2 and their physical properties are shown in Table IC along with the results of Examples 1 and 2. In column I of phase transition points in Table 1, C indicates a crystalline phase, N indicates a nematic phase, I indicates an isotropic liquid phase, and () indicates a monotropic transition. Also, η2° is 2
Shows the viscosity at 0°C. Table 1 (Δn, Δε in two
and η2° are values determined by extrapolation from the characteristic values of a composition prepared according to Example 26 (Usage Example) described later.
実施例２６（使用例）
Ｃ，Ｈ，ベア〉（コヒＣＮ ２４部（重凝、以下
同じ）Ｃ５１１１１ＸＥ８回＞ＣＮ ３６部Ｃ７
Ｈ１５＜→べ◇シＮ ２５部からなる液晶組成物
ＡのＮＩ点は７２．０ ℃、η２゜は２７．８ ｃｐ、
Δｎは０．１４０（ｎｅ ＝ １．６３２、ｎｏ ＝１
．４９２）であり、これをセル厚１０μ鴇のＴＮセル（
二封入し２５℃にてｍす定したΔεは１１．０（ε、、
＝ １５．７、εよ＝４．７）であり、しきい値電圧
は１．７５ Ｖ％飽和電圧は２．５９ ｖであった。Example 26 (Example of use) C, H, Bear> (Kohi CN 24 parts (heavy coagulation, the same hereinafter) C51111XE 8 times>CN 36 parts C7
The NI point of liquid crystal composition A consisting of 25 parts of H15<→be◇N is 72.0°C, η2° is 27.8 cp,
Δn is 0.140 (ne = 1.632, no = 1
．． 492), which is a TN cell with a cell thickness of 10 μm (
Δε of 2 sealed cells and fixed at 25℃ is 11.0(ε,,
= 15.7, ε = 4.7), the threshold voltage was 1.75 V%, and the saturation voltage was 2.59 V.
該液晶！ｌ成物Ａ８５重揄部に実施例１で合成した化合
物を１５屯４部加えた液晶組成物のＮＩ点は７６．８℃
と上昇し１η２ｏは３１．１ ｃＰとなり・△ｎは０．
１５１ （ｎｅ＝ｌ、５４５、ｎｏ＝１，４９４）と上
昇した。この組成物を１〕述のＴＮセルに封入し２５℃
にて測定したΔεは９．８（ε、＝１４．２、ｔＬ＝
４．４ ） トナＩＪ、しきイ値ｉ圧ハ１．７７ Ｖ
。The LCD! The NI point of a liquid crystal composition prepared by adding 4 parts of 15 tons of the compound synthesized in Example 1 to 85 parts of compound A is 76.8°C.
and 1η2o becomes 31.1 cP. △n becomes 0.
The number increased to 151 (ne=l, 545, no=1,494). This composition was sealed in the TN cell described in 1) and heated at 25°C.
Δε measured at 9.8 (ε, = 14.2, tL =
4.4) Toner IJ, threshold i pressure 1.77 V
.
飽和電圧は２．６１ Ｖとなった。The saturation voltage was 2.61V.
実施例２７（使用例）
実施例２６で示した液晶組成物Ａ８５重陽部に実施例２
で示した化合物を１５重量部加えた液晶組成物のＮＩ点
は７４．４℃と上昇し・η２゜は３４，７ ｃＰとなり
、Δｎは０．１４９ （ｎｅ ＝１．６４７、ｎｏ＝１
．４９８）と上昇した。この組成物をセル厚１０μ悔の
ＴＮセルに封入し２５℃Ｃ：て測定したΔｅは１０．２
（ｔ、、＝ １４．９、ε上＝４．７）となり、しき
い値電圧は１．７４ Ｖ 、飽和電圧は２．４０ Ｖと
減少した。Example 27 (Usage example) Example 2 was added to the liquid crystal composition A85 double positive part shown in Example 26.
The NI point of the liquid crystal composition to which 15 parts by weight of the compound shown in was added increased to 74.4°C, η2° became 34.7 cP, and Δn was 0.149 (ne = 1.647, no = 1
．． 498). This composition was sealed in a TN cell with a cell thickness of 10 μm and the Δe measured at 25°C was 10.2.
(t, , = 14.9, ε upper = 4.7), the threshold voltage decreased to 1.74 V, and the saturation voltage decreased to 2.40 V.
実施例２日（使用例）
実施例２６で示した液晶組成物Ａ８５重量部（二実施例
１８で示した化合物を１５重量部加えた液晶組成物のＮ
Ｉ点は６８．９℃となり、η２゜は３０．１ ｃＰとな
り、Δｎは０．１４９と上昇した。Example 2 (Usage Example) 85 parts by weight of the liquid crystal composition A shown in Example 26 (2 N of the liquid crystal composition to which 15 parts by weight of the compound shown in Example 18 was added)
Point I was 68.9°C, η2° was 30.1 cP, and Δn increased to 0.149.
この組成物をセル厚１０μｍのＴＮセル（：封入して２
５℃（：て測定したΔ８は１０．０ （ε、＝１４，５
、ｅふ＝４．５）となり、しきい値電圧は１．７１ Ｖ
、飽和ＱＩＩＥは２，５３ Ｖと減少した。This composition was sealed in a TN cell with a cell thickness of 10 μm (2
Δ8 measured at 5℃ (: 10.0 (ε, = 14,5
, eF=4.5), and the threshold voltage is 1.71 V.
, the saturated QIIE decreased to 2,53 V.
実施例２９（使用例）
実施例２６で示した液晶組成物Ａ８５重清部（二実施例
１５で示した化合物を１５重量部加えた液晶組成物のＮ
Ｉ点は６６．３℃となり、η２゜は３０．５ ｃＰとな
り・Δｎは０．１４５と上昇した。Example 29 (Example of use) N of the liquid crystal composition to which 15 parts by weight of the compound shown in Example 15 was added (2 parts by weight of the liquid crystal composition A85 shown in Example 26)
Point I was 66.3°C, η2° was 30.5 cP, and Δn increased to 0.145.
この組成物をセル厚１０μ鴨のＴＮセルに封入し２５℃
Ｃ：て氾１１定したΔｅは１２．１ （ｇ、、： ｌ
６．５．１、＝ ４．４ ）と上昇し、しきい値電圧は
１．６４Ｖ。This composition was sealed in a TN cell with a cell thickness of 10 μm and heated at 25°C.
C: The constant Δe is 12.1 (g,,: l
6.5.1, = 4.4), and the threshold voltage was 1.64V.
飽和電圧は２．２４ Ｖと減少した。The saturation voltage decreased to 2.24V.
〔発明の効果〕
本発明により表示装置用の液晶材料の成分として用いら
れる新規な液晶性化合物および光の屈折率異方性の大き
い液晶組成物が提供できる。[Effects of the Invention] The present invention can provide a novel liquid crystal compound used as a component of a liquid crystal material for a display device and a liquid crystal composition having a large optical refractive index anisotropy.
また、本発明には液晶材料の選択の範囲を拡張するとい
う効果もある。The present invention also has the effect of expanding the range of selection of liquid crystal materials.
以上that's all
Claims (2)
１２のアルコキシ基、フッ素またはシアノ基を示し、Ｙ
は−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−を示し、Ｒは炭素数
１〜１２のアルキル基または炭素数１〜１２のアルコキ
シ基を示す。） で表わされるピリミジン化合物。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X is an alkyl group having 1 to 12 carbon atoms,
12 alkoxy group, fluorine or cyano group, Y
represents -CH=CH- or -C≡C-, and R represents an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. ) A pyrimidine compound represented by
１２のアルコキシ基、フッ素またはシアノ基を示し、Ｙ
は−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−を示し、Ｒは炭素数
１〜１２のアルキル基または炭素数１〜１２のアルコキ
シ基を示す。） で表わされるピリミジン化合物を少なくとも１種含有す
ることを特徴とする液晶組成物。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X is an alkyl group having 1 to 12 carbon atoms,
12 alkoxy group, fluorine or cyano group, Y
represents -CH=CH- or -C≡C-, and R represents an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. ) A liquid crystal composition comprising at least one pyrimidine compound represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20282186A JPS6360972A (en) | 1986-08-29 | 1986-08-29 | Pyrimidine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20282186A JPS6360972A (en) | 1986-08-29 | 1986-08-29 | Pyrimidine compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6360972A true JPS6360972A (en) | 1988-03-17 |
Family
ID=16463751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20282186A Pending JPS6360972A (en) | 1986-08-29 | 1986-08-29 | Pyrimidine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6360972A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4906400A (en) * | 1987-06-01 | 1990-03-06 | Chisso Corporation | Smetic liquid crystal compound |
| US5068053A (en) * | 1987-03-27 | 1991-11-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Ethyne derivatives as a component of liquid crystal phases |
| AU642183B2 (en) * | 1989-12-29 | 1993-10-14 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a substituted phenyl group having retinoid like activity |
-
1986
- 1986-08-29 JP JP20282186A patent/JPS6360972A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068053A (en) * | 1987-03-27 | 1991-11-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Ethyne derivatives as a component of liquid crystal phases |
| US4906400A (en) * | 1987-06-01 | 1990-03-06 | Chisso Corporation | Smetic liquid crystal compound |
| AU642183B2 (en) * | 1989-12-29 | 1993-10-14 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a substituted phenyl group having retinoid like activity |
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