JPS63253075A - Novel pyrimidine derivative - Google Patents
Novel pyrimidine derivativeInfo
- Publication number
- JPS63253075A JPS63253075A JP8693987A JP8693987A JPS63253075A JP S63253075 A JPS63253075 A JP S63253075A JP 8693987 A JP8693987 A JP 8693987A JP 8693987 A JP8693987 A JP 8693987A JP S63253075 A JPS63253075 A JP S63253075A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- reacting
- phase
- 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
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract description 4
- 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 abstract description 3
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000011734 sodium Substances 0.000 abstract description 3
- 229910052708 sodium Inorganic materials 0.000 abstract description 3
- 239000012769 display material Substances 0.000 abstract description 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 abstract 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 19
- 239000004990 Smectic liquid crystal Substances 0.000 description 11
- 230000001747 exhibiting effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- JMVFRBIAXHMBPB-KKFHFHRHSA-N (3s)-3-amino-4-(2-diphenoxyphosphorylpyrrolidin-1-yl)-4-oxobutanamide Chemical compound NC(=O)C[C@H](N)C(=O)N1CCCC1P(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 JMVFRBIAXHMBPB-KKFHFHRHSA-N 0.000 description 1
- -1 4-n-pentyloxyphenyl Chemical group 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
Abstract
Description
【発明の詳細な説明】
〔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新規ピリミシ
ン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel pyrimicine derivatives useful as electro-optic display materials.
近年、大型液晶ディスプレイにエヌ・ニー命クラーク（
Ｎ−Ａ−Ｃ１ａｒｋ ）等によって提案された強誘電性
液晶を利用した高速応答性に優れた液晶表示セルが使用
されている。この表示セルはカイラルスメクチックＣ相
（以下、ＳＣ０相という、）の光スイツチング現象を応
用したものであシ、このようなＳｅ 相を示す液晶材
料としては、スメクチックＣ相（以下、Ｓｃ相という、
）を示す混合液晶に強誘電性カイラル化合物を添加して
調製されるタイグのカイラルスメクチック混合液晶が有
効である。In recent years, N.M. Clark (
A liquid crystal display cell with excellent high-speed response using ferroelectric liquid crystal proposed by N-A-C1ark et al. has been used. This display cell applies the optical switching phenomenon of chiral smectic C phase (hereinafter referred to as SC0 phase).As a liquid crystal material exhibiting such Se phase, smectic C phase (hereinafter referred to as Sc phase) is used.
) is effective.Taig's chiral smectic mixed liquid crystal, which is prepared by adding a ferroelectric chiral compound to a mixed liquid crystal exhibiting the following properties, is effective.
この種の表示セルに広い動作温度範囲を確保するために
は、使用されるカイ２ルスメクチック混合液晶が広い温
度範囲でＳＣ０相を示し得るものでなければならない。In order to ensure a wide operating temperature range for this type of display cell, the chi2lsmectic mixed liquid crystal used must be capable of exhibiting the SC0 phase over a wide temperature range.
また、このように広い温度範囲で８ｅ”相を示すカイラ
ルスメクチック混合液晶をｌ！ｌＩ製する際、強誘電性
カイラル化合物を添加すべき相手のスメクチック混合液
晶として広い温度範囲でＳｃ相を示すものを使用すれば
効果的である。In addition, when producing a chiral smectic mixed liquid crystal that exhibits an 8e'' phase over a wide temperature range, the ferroelectric chiral compound should be added to a smectic mixed liquid crystal that exhibits an Sc phase over a wide temperature range. It is effective if you use
そして、広い温度範囲でｇｏ相を示すスメクチック混合
液晶を調製する方法として、一般的に、低い温度領域で
Ｓｅ相を示すスメクチック液晶と高い温度領域でＳｅａ
を示すスメクチック液晶を混合してｖ！４製する方法が
採られるので、その調製材料としてＢｅ相温度範囲の異
なる各１スメクチック液晶化合物特に広り温度範囲でＳ
ｅ相を示すスメクチック液晶化合物の提供が望まれてい
る。As a method for preparing a smectic mixed liquid crystal that exhibits a Go phase in a wide temperature range, a smectic liquid crystal that exhibits a Se phase in a low temperature range and a Sea phase in a high temperature range are generally used.
By mixing smectic liquid crystals that show v! Since the preparation method is adopted, each smectic liquid crystal compound with different Be phase temperature range is used as the preparation material, especially S in a wide temperature range.
It is desired to provide a smectic liquid crystal compound exhibiting an e-phase.
本発明が解決しようとする問題点は、広い温度範囲でＳ
ｅ相を示す液晶化合物の提供にある。The problem to be solved by the present invention is that S
An object of the present invention is to provide a liquid crystal compound exhibiting an e-phase.
本発明は、上記問題点を解決するなめに。 The present invention aims to solve the above problems.
一般式
（式中、Ｒ及びＲ′は各々独立的に炭素原子数１〜２０
のアルキル基を表わす。）
で表わされる化合物を゛提供する。General formula (wherein R and R' each independently have 1 to 20 carbon atoms)
represents an alkyl group. ) is provided.
本発明に係る式（Ｉ）の化合ｖＪは、久の裏道方法に従
って製造することができるや
（上記式〇）〜荀の各式にかけるＲ及びＲ′は夫々式（
１）におけるＲ及びＲ′と同じ意味をもつ。）Ｋ１段階
一式■の化合物に、Ｎ、Ｎ−ジメチルホルムアミドとオ
キシ塩化リンから調整したビスマイヤー（Ｖｌｌｓｍ＠
ｉ＠ｒ ）試薬と反応させた後、過塩素酸又は過塩素酸
マグネシウムと反応させて式（ト）の化合物を製造する
。大面の化合物は精製することなく、久の反応に使用す
る。The compound vJ of the formula (I) according to the present invention can be produced according to Ku's back-road method.
It has the same meaning as R and R' in 1). ) K1 stage set ■ compound prepared from N,N-dimethylformamide and phosphorus oxychloride (Vllsm@
i@r) After reacting with a reagent, the compound of formula (g) is produced by reacting with perchloric acid or magnesium perchlorate. The large-sized compound is used in the next reaction without being purified.
藁２段階−第１段階で製造した粗製の式（２）の化合物
と式ωのベンツアミリン誘導体とをアルコール中でナト
リウムアルコラード存在下で反応させる。Step 2 - The crude compound of formula (2) prepared in step 1 is reacted with a benzamyrin derivative of formula ω in alcohol in the presence of sodium alcoholade.
反応生成物に対して、溶媒抽出、水洗、乾燥、再結晶等
の精製処理を施すことによって、目的とする式（Ｉ）の
化合寄金単離することができる。The desired compound of formula (I) can be isolated by subjecting the reaction product to purification treatments such as solvent extraction, water washing, drying, and recrystallization.
斯くして製造された式（１）で示される代表的な化合物
の転移温度金ｉ１！ｉ表に掲げる。The transition temperature of the representative compound represented by formula (1) thus produced is gold i1! Listed in Table i.
ｙｊＩＦＪｌ 衆
１３４ （Ｓａ、ｌ：Ｎ ）
ｘ７７（ｓ；：Ｂ
２ ｎ−Ｃ，Ｈ，、−ｎ−０５Ｈ１１”’ ９
２（Ｃ−＋５ｅ）１３６ （Ｓｏ、：Ｎ ）
ｘ７４（Ｎ；：ｘ）
（表中、Ｃは結晶相、ＳａはスメクチックＣ相、Ｎはネ
マチック相、Ｉは等方性液体相を夫々貴わす。］
第１真から本発明の化合物が広い温度範囲でＳｅ相を示
すことがわかる。yjIFJl 134 (Sa, l:N) x77(s;:B 2 n-C,H,, -n-05H11”' 9
2(C-+5e)136 (So, :N) x74(N;:x) (In the table, C represents the crystalline phase, Sa represents the smectic C phase, N represents the nematic phase, and I represents the isotropic liquid phase, respectively. ] From the first true value, it can be seen that the compound of the present invention exhibits a Se phase over a wide temperature range.
実施例Ｉ
Ｎ、Ｎ −ソメチＡ／ ｙｅｔ ルｂ ７ミド７３．２
ｇ（１，００モルンとオキシ塩化リン９２．９ （０，
６０モル）全５℃以下で反応させ、ビスマイヤー試薬’
ｉｓａした。次いで、４−ｎ−ペンチルオキシフェニル
酢１１４４．４９ （０，２０モル］を加え、室温で１
時間反応させた後、８０℃で５時間反応させた。反応終
了後、０℃以下で水１００−を加えた後、過塩素酸マグ
ネシウム４４．８１ （０，２０モ＃ ） ｋＭＪＬ、
１時間攪拌し、析出する結晶を濾過し、水洗、エーテル
洗浄後、減圧乾燥し、下記化合物７２１７（０，□１９
モル）を得九。Example I N,N-someti A/yet rub 7mid 73.2
g (1,00 morn and phosphorus oxychloride 92.9 (0,
60 mol) React at a temperature below 5°C, and add Bismayer's reagent
Isa did it. Next, 1144.49 (0.20 mol) of 4-n-pentyloxyphenyl vinegar was added, and 1
After reacting for an hour, the reaction was continued at 80° C. for 5 hours. After the reaction was completed, 100% of water was added at 0°C or below, and magnesium perchlorate was added to 44.81 (0.20 mo#) kMJL,
After stirring for 1 hour, the precipitated crystals were filtered, washed with water and ether, and dried under reduced pressure to obtain the following compound 7217 (0, □19
mole) obtained nine.
次いで、上記化合物１０．２．！ｉ’（０，０２６モル
ンと２−フロロ−４−ｎ−ノニルオキシペンツアミノン
塩酸塩７．９９ （０，０２６モル）１に無水エタノー
ル１００ｄに溶解し、この溶液に０．１３モル当量のナ
トリウムエトキサイド・エタノール溶液を滴下した後、
６時間加熱還流する０反応終了後、生成ｗ’ｔトルエン
で抽出、水洗した後、溶媒を減圧留去する。Then, the above compound 10.2. ! i' (0,026 mol and 7.99 (0,026 mol) of 2-fluoro-4-n-nonyloxypentzaminone hydrochloride) was dissolved in 100 d of absolute ethanol, and 0.13 molar equivalent of sodium was added to this solution. After dropping the ethoxide/ethanol solution,
After the reaction is heated and refluxed for 6 hours, the mixture is extracted with toluene produced, washed with water, and the solvent is distilled off under reduced pressure.
得られた粗生成物をエタノールで２回再結晶精製して、
下記化合物６．２ ｇ（０，０１３モル）全得た。The obtained crude product was purified by recrystallization twice with ethanol,
A total of 6.2 g (0,013 mol) of the following compound was obtained.
転移温度 ８５℃（Ｃ−＋Ｓｅ ） １３４℃（ｓ 、 ：Ｎ） １７７℃（Ｎ二Ｉ） 収 軍 ５０チ 実施例２ 実施例１と同様にして下記化合物を得た。Transition temperature 85℃ (C-+Se) 134℃ (s, :N) 177℃ (N2I) Collection: Army 50 Chi Example 2 The following compound was obtained in the same manner as in Example 1.
転移温度 ９２℃（Ｃ→Ｂｅ）
１３６℃（Ｓｃ’：：Ｎ ）
１７４℃（Ｎニエ）
収 軍 ５４％
〔発明の効果〕
本発明に係る式（１）の化合物は、広い温度範囲で８ｅ
相を示す新規な液晶化合物である。従って、本発明に係
る式（１）の化合物は強誘電性液晶を利用した茨示セル
の液晶材料として有用である。Transition temperature 92°C (C→Be) 136°C (Sc'::N) 174°C (Nier) Convergence temperature 54% [Effects of the invention] The compound of formula (1) according to the present invention has a temperature of 8e over a wide temperature range.
This is a new liquid crystal compound that exhibits a phase. Therefore, the compound of formula (1) according to the present invention is useful as a liquid crystal material for a thorn display cell using ferroelectric liquid crystal.
手続補正書（自発）
昭和６２年５月２０日
昭和６２年特許願第８６９３９号
２、発明の名称
新規ピリミジン誘導体
３、補正をする者
事件との関係 特許出願人
〒１７４ 東京都板橋区坂下三丁目３５番５８号（２８
８）大日本インキ化学工業株式会社代表者 用 村
茂 邦
４、代理人
〒１０３ 東京都中央区日本橋三丁目７番２０号大日
本インキ化学工業株式会社内
電話 東京（０３）２７２−４５１１ （大代表）（８
８７６）弁理士高橋勝利
５、補正の対象
６、補正の内容
（１）明細書第３頁第９行目における
「〔問題を解決するための手段〕」を
「〔問題点を解決するための手段〕」に補正する。Procedural amendment (spontaneous) May 20, 1988 Patent Application No. 86939 2, Title of invention: New pyrimidine derivative 3, Relationship with the person making the amendment Patent applicant: San Sakashita, Itabashi-ku, Tokyo, 174 Chome 35-58 (28
8) Dainippon Ink & Chemicals Co., Ltd. Representative: Shigeru Kuni Mura 4, Agent Address: 3-7-20 Nihonbashi, Chuo-ku, Tokyo 103 Dainippon Ink & Chemicals Co., Ltd. Telephone: Tokyo (03) 272-4511 (Dainippon Ink & Chemicals Co., Ltd.) Representative) (8
876) Patent Attorney Katsutoshi Takahashi 5, Subject of amendment 6, Contents of amendment (1) "[Means for solving the problem]" in line 9 of page 3 of the specification has been changed to "[Means for solving the problem]" means]”.
（２）明細書第４頁第１０行目から第１１行目における 「ビスマイヤー」を ｒビルスマイヤー」に 補正する。(2) In lines 10 to 11 of page 4 of the specification "Bismeyer" r Bilsmeyer” to correct.
（３） 明細書第６頁第１２行目釦おける「ビスマイ
ヤー」を
「ビルスマイヤー」に
補正する。(3) "Bissmeyer" in the button on page 6, line 12 of the specification shall be amended to "Vilsmeyer".
以 上that's all
Claims (1)
の直鎖状アルキル基を表わす。） で表わされる化合物。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R and R' each independently have a carbon atom number of 1 to 20
represents a straight-chain alkyl group. ) A compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8693987A JPS63253075A (en) | 1987-04-10 | 1987-04-10 | Novel pyrimidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8693987A JPS63253075A (en) | 1987-04-10 | 1987-04-10 | Novel pyrimidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63253075A true JPS63253075A (en) | 1988-10-20 |
Family
ID=13900838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8693987A Pending JPS63253075A (en) | 1987-04-10 | 1987-04-10 | Novel pyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63253075A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4900473A (en) * | 1987-10-20 | 1990-02-13 | Chisso Corporation | Optically active alkanoyloxy 2,5-diphenyl pyrimidine and liquid crystal compositions |
| US4900472A (en) * | 1987-10-20 | 1990-02-13 | Chisso Corporation | 2,5-diphenyl pyrimidine compounds and liquid crystal compositions |
| US4997942A (en) * | 1988-04-25 | 1991-03-05 | Dainippon Ink And Chemical, Inc. | 2,4-disubstituted pyrazine derivatives, pyrimidine derivatives, and liquid crystal containing the same |
-
1987
- 1987-04-10 JP JP8693987A patent/JPS63253075A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4900473A (en) * | 1987-10-20 | 1990-02-13 | Chisso Corporation | Optically active alkanoyloxy 2,5-diphenyl pyrimidine and liquid crystal compositions |
| US4900472A (en) * | 1987-10-20 | 1990-02-13 | Chisso Corporation | 2,5-diphenyl pyrimidine compounds and liquid crystal compositions |
| US4997942A (en) * | 1988-04-25 | 1991-03-05 | Dainippon Ink And Chemical, Inc. | 2,4-disubstituted pyrazine derivatives, pyrimidine derivatives, and liquid crystal containing the same |
| US5128472A (en) * | 1988-04-25 | 1992-07-07 | Dainippon Ink And Chemicals, Inc. | 2,5-disubstituted pyrazine derivatives, pyrimidine derivatives, and liquid crystal containing the same |
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