JPS60204732A - Novel phenylalkylethylenic nematic liquid crystal compound - Google Patents
Novel phenylalkylethylenic nematic liquid crystal compoundInfo
- Publication number
- JPS60204732A JPS60204732A JP5959084A JP5959084A JPS60204732A JP S60204732 A JPS60204732 A JP S60204732A JP 5959084 A JP5959084 A JP 5959084A JP 5959084 A JP5959084 A JP 5959084A JP S60204732 A JPS60204732 A JP S60204732A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound shown
- compound
- liquid crystal
- give
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
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フェニルアル
キルエチレン系新規ネマチック液晶化合物に関する。本
発明によって提供される新規ネマチック液晶化合物は一
般式
で表わされる化合物でるる。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel phenylalkylethylene-based nematic liquid crystal compound useful as an electro-optical display material. The novel nematic liquid crystal compound provided by the present invention is a compound represented by the general formula.
液晶表示セルの代表的なものにエム・シャット(M−8
@hadt)等(APPLIED P)iYsIc8
LETTIR818,127〜128(1971))に
工って提案された電界効果域セル(フィールド・エフェ
クト・モ・−ド・セル)又はジーeエイチ11バイルマ
イヤー(GeHH@i1m@i@r)等(PROCEE
DING OF THE 1.E、JE、 56116
2〜1171(196B))にぶって提案された動的光
散型セル(ダイミック・スキャツタリング・モード・セ
ル)又Lジー・エイチ11/Nイル”yイヤー(GeH
Hallmeier)等(APPLIED PIiY8
IC8LETTER813、91(196B))あるい
はディー書エル魯ホワイト(D LWhite )等(
JOURNAL OF APPLIED PHY8IC
845,4718(1,&74))によって提案された
ゲスト・ホスト型セルなどが必る。M-Shut (M-8) is a typical liquid crystal display cell.
@hadt) etc. (APPLIED P)iYsIc8
LETTIR 818, 127-128 (1971)) or the field effect mode cell proposed by GeHH11 Beilmeier (GeHH@i1m@i@r), PROCEE
DING OF THE 1. E, JE, 56116
2-1171 (196B)) and the dynamic scattering mode cell proposed in GeH 11/N
Hallmeier) etc. (APPLIED PIiY8
IC8LETTER813, 91 (196B)) or D LWhite etc. (
JOURNAL OF APPLIED PHY8IC
845, 4718 (1, & 74)), etc. are necessary.
これらの液晶表示セルの中で現在主流をなすものは、電
界効果型セルの一種のTN型セルである。このTNJセ
ルにおいては、 G、BauerによってMo7. C
rygt、 Liq。Among these liquid crystal display cells, the one currently mainstream is a TN type cell, which is a type of field effect cell. In this TNJ cell, Mo7. C
rygt, Liq.
Cryst、63 45 (1981)に報告されてい
る工うIc。Ic as reported in Cryst, 63 45 (1981).
セル外観を損う原因となるセル表面での干渉縞の発生を
防止するために、セルに充填される液晶材料の屈折率の
異方性(Δn)とセルの厚さくd)μmの積を成る特定
の値に設定する必要がおる。実用的に使用される液晶表
示セルでは、Δn@dの値が0.5. 1.0,1.6
又は2.2のいずれかに設定されている。この↓うにΔ
n@dの値が一定値に設定されるから、Δnの値の大き
な液晶材料を使用すれば、dの値を小ならしめることが
できる。dの値が小となれは、応答時Is!lI(τ)
は、よく知られたταd2の関係式に従って小となる。In order to prevent interference fringes from occurring on the cell surface, which can cause damage to the cell appearance, the product of the refractive index anisotropy (Δn) of the liquid crystal material filled in the cell and the cell thickness d) μm is calculated. It must be set to a specific value. In a practically used liquid crystal display cell, the value of Δn@d is 0.5. 1.0, 1.6
or 2.2. This↓uniΔ
Since the value of n@d is set to a constant value, the value of d can be made small by using a liquid crystal material with a large value of Δn. If the value of d is small, Is! lI(τ)
becomes small according to the well-known relational expression of ταd2.
さらに応答時間(τ)は液晶材料の粘度(η)と比例関
係(τにη)がある。すなわちΔnの値が大きく低粘度
の液晶材料は高速応答の液晶表示セル會製作するのに極
めて重要な材料である。Furthermore, the response time (τ) has a proportional relationship (η to τ) with the viscosity (η) of the liquid crystal material. In other words, a liquid crystal material with a large value of Δn and low viscosity is an extremely important material for manufacturing a liquid crystal display cell with high-speed response.
一方、実用可能な液晶材料の多くは、通常、室温付近に
ネマチック相ケ有する化合物と室温より高い温度領域に
ネマチック相を有する化合物から成る数棟又はそれ以上
の成分を混合することによってII製される。現在実用
的に使用される上記の如き混合成品の多くは、少なくと
も一60℃〜+65℃の全温度範囲に亘ってネマチック
相會有することが賛求されているが、液晶表示セルの応
用製品の多様化に伴ない、ネマチック液晶温度範囲を更
に高温[1c拡張した液晶材料が要望されている。On the other hand, most of the liquid crystal materials that can be put to practical use are usually manufactured by mixing several or more components consisting of a compound that has a nematic phase near room temperature and a compound that has a nematic phase above room temperature. Ru. Most of the above-mentioned mixed products currently in practical use are expected to have a nematic interaction over the entire temperature range of -60°C to +65°C, but it is said that many of the above-mentioned mixed products currently in practical use have a nematic interaction over the entire temperature range of -60°C to +65°C. With the diversification, there is a demand for liquid crystal materials that extend the temperature range of nematic liquid crystals to even higher temperatures [1c].
現在、高速応答の液晶表示セル?I−製作するために用
いらアルキル基t−表わす。)で表わされる化合物等が
あるが。Currently, fast-response liquid crystal display cells? I- represents the alkyl group used to produce t-. ), etc.
これらの材料は混合液晶の粘度を低下させることができ
ても反面、ムnおよびN−I転移温度を低下させるとい
う欠点tもっている。Although these materials can lower the viscosity of the mixed liquid crystal, they have the disadvantage of lowering the molar and N-I transition temperatures.
本発明に係る式CI)の化合物は、この欠点の改善され
たものでメ9.低粘度で比較的Δnが高く、然も高いN
−I転移温度を有する新規なネマチック液晶化合物であ
る。従って、各棟の母体液晶に式CI)の化合物を混合
することによって、低粘度で大きなΔnと高いN−I転
移温度を有する混合液晶材料t−調製することができる
。The compound of formula CI) according to the present invention has improved this drawback and has the following advantages: Low viscosity, relatively high Δn, and high N
-I is a novel nematic liquid crystal compound having a transition temperature. Therefore, by mixing the compound of formula CI) with the parent liquid crystal of each building, it is possible to prepare a mixed liquid crystal material t- having a low viscosity, a large Δn, and a high N-I transition temperature.
本発明に係る式(I)の化合物は次の製造方法に従って
製造することかできる。下記(II)〜(V)の各式に
おけるR及びR′は夫々式(1)におけるR及びR′と
同じ意味會も9゜
第1 &階−トランス4− n−アルキル−1−フェニ
ルシクロヘキサンに二貴化炭素めるいはニトロベンゼン
中で式(n)の化合物と無水塩化アルミニウムを反応さ
せて式Cm)の化合物′t−製造する。The compound of formula (I) according to the present invention can be produced according to the following production method. R and R' in each of the following formulas (II) to (V) have the same meaning as R and R' in formula (1), respectively. Then, a compound of formula (n) is reacted with anhydrous aluminum chloride in noble carbon dioxide or nitrobenzene to produce a compound of formula Cm).
第2段階−第1段階で製造された式(11)の化合物に
無水エーテルあるいは無水テトラヒドロフラン中で水素
化リチクムアルミニウムの如き還元剤を反応させて式(
IV)の化合物全製造する。Second step - The compound of formula (11) produced in the first step is reacted with a reducing agent such as lyticum aluminum hydride in anhydrous ether or anhydrous tetrahydrofuran to form a compound of formula (11).
The entire compound of IV) is prepared.
WJ6段階−第2段階で製造された粗製の式(IV)の
化合物に、(jHk水素カリウムの如き脱水剤を加え加
熱し脱水して式(V)の化合物’klll造する。WJ Step 6 - To the crude compound of formula (IV) produced in the second step, a dehydrating agent such as (jHk potassium hydrogen) is added and heated to dehydrate to produce a compound of formula (V).
斯くして製造される式(I)の化合物の代表的なものの
転移温度、粘度及びnnを第1衣に掲げる。The transition temperature, viscosity and nn of representative compounds of formula (I) thus produced are listed in the first column.
第 1 表
A RR’ 転移温度粘度/2 ffL;△n/25℃
(”C) (C,P、) (−)
C→N Nl1
1c、n、 −−cH,54518,50,1232n
−C3)1.−−C)1337 85 B、6 0.1
485 n−C4B、 −−C)l、 34 7B 1
0.2 Q、1344 nn−C6HH−−C,279
210,30,1385n−C,H,、−−C)l、
38 C912,50,130第1表に掲示したデータ
から、式(I)の化合物は)J−I転移温度が高く、ネ
マチック温度範囲も広く、低粘度でnnも比戟的高いこ
とが容易に理解できる。Table 1 A RR' Transition temperature viscosity/2 ffL; △n/25°C
(”C) (C,P,) (-) C→N Nl1 1c, n, --cH, 54518, 50, 1232n
-C3)1. --C) 1337 85 B, 6 0.1
485 n-C4B, --C)l, 34 7B 1
0.2 Q, 1344 nn-C6HH--C, 279
210,30,1385n-C,H,,--C)l,
38 C912, 50, 130 From the data posted in Table 1, it is easy to see that the compound of formula (I) has a high J-I transition temperature, a wide nematic temperature range, a low viscosity, and a relatively high nn. It can be understood.
本発明に係る式(1)の化合物は弱い負の誘電率異方性
を有するネマチック液晶化合物であ九従って例えば、負
又は弱い正の誘電率異方性を有する他のネマチック液晶
化合物との混合物の状態で動的光散乱量表示セルの材料
として使用することができ、また強い正の誘電率異方性
を有する他のネマチック液晶化合物との混合物の状態で
電界効果型表示セルの材料として使用することができる
。The compound of formula (1) according to the present invention is a nematic liquid crystal compound having a weak negative dielectric anisotropy. Therefore, for example, it may be mixed with other nematic liquid crystal compounds having a negative or weak positive dielectric anisotropy. It can be used as a material for dynamic light scattering display cells in the state of can do.
このように、式(I)の化合物と混合して使用すること
のできる好ましい代表例としては、例えば4,4′−置
換安息香酸フェニルエステル、4.4’−置換シクロヘ
キサンカルボン酸フェニルエステル、ar4’−fll
ジシクロヘキサンカルボン酸フェニルエステル、a(4
−[換シクロへΦサンカルボニルオキシ〕安息香M4’
−[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ヒ置換シクロヘキシルエステ
ル、4.4’−置換ビフェニル、4.4’−置換フェニ
ルシクロヘキサン、4.4’−置換ビフェニル、4.4
’−ビフェニルシクロヘキサン%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。Thus, preferred representative examples which can be used in admixture with compounds of formula (I) include, for example, 4,4'-substituted benzoic acid phenyl ester, 4,4'-substituted cyclohexanecarboxylic acid phenyl ester, ar4 '-flll
Dicyclohexanecarboxylic acid phenyl ester, a(4
-[cyclocyclotoΦsancarbonyloxy]benzoic acid M4'
-[substituted phenyl ester 4 (4-substituted cyclohexyl)
Benzoic acid 4'-substituted phenyl ester, 4(4-substituted cyclohexyl)benzoic acid 4-substituted cyclohexyl ester, 4.4'-substituted biphenyl, 4.4'-substituted phenylcyclohexane, 4.4'-substituted biphenyl, 4 .4
Examples include '-biphenylcyclohexane%2(4'-substituted phenyl)5-substituted pyrimidine.
実施例 に
価化炭素250a中に無水塩化アルミニウム24.0#
(0,180moJ)i加え、加熱還流させながら、こ
の鹸液(D中K トランス−4−n −フロピルー1−
フェニルシクロヘキサン30.3# (0,150mo
J)とプロピオニルクロライド1五9#(0,150m
o7)の混会物km下した。Example Anhydrous aluminum chloride 24.0# in valent carbon 250a
(0,180 moJ) was added to this soap solution (K trans-4-n-furopyru-1-
Phenylcyclohexane 30.3# (0,150mo
J) and propionyl chloride 159# (0,150m
o7) mixture was lowered by km.
1時間加熱還流した後、二ば化炭素を留去し、生成物t
氷水中に加え60℃で1時間攪拌した。冷却後生成物を
トルエンで抽出し、水洗、乾燥し、トルエンを留去後エ
タノールで再結晶精製し、下記化合中3t4A’(0,
122moJ)全書た。After heating under reflux for 1 hour, carbon dioxide was distilled off and the product t
The mixture was added to ice water and stirred at 60°C for 1 hour. After cooling, the product was extracted with toluene, washed with water, dried, and after distilling off the toluene, it was purified by recrystallization with ethanol to obtain 3t4A'(0,
122moJ) Completely written.
この化合物を無水テトラヒドロフランに浴解しfcm液
t−水素化リチウムアルミニウム4.63& (0,1
22moJ)と無水テトラヒドロフラン150継の混合
溶液中に滴下した。This compound was bath dissolved in anhydrous tetrahydrofuran and FCM liquid t-lithium aluminum hydride 4.63 & (0,1
22 moJ) and 150 parts of anhydrous tetrahydrofuran.
室温で2時間反応させた後、反応液に9qbRC1l
200wIV及び水200117!’に加え、生成物t
トルエンで抽出、水洗、乾燥し、抽出液からトルエンを
留去した。得られた結晶全トルエン300−に浴解し、
この−液に硫酸水素カリウムo、s y@加え、デカン
タ−で水を除きながら、1時間加熱還流した。反応後1
反応液を水洗、乾燥しトルエンを留去後生酸物をエタノ
ールで再結晶精製し、下記化合物19.2IC0,07
95mol)ve得た。After reacting at room temperature for 2 hours, add 1 l of 9qbRC to the reaction solution.
200wIV and water 200117! ' plus the product t
Extracted with toluene, washed with water, dried, and toluene was distilled off from the extract. The obtained crystals were dissolved in 300% of total toluene,
Potassium hydrogen sulfate o, sy@ was added to this solution, and the mixture was heated under reflux for 1 hour while removing water with a decanter. After reaction 1
The reaction solution was washed with water, dried, toluene was distilled off, and the raw acid was purified by recrystallization with ethanol to obtain the following compound 19.2 IC0.07
95 mol)ve was obtained.
収 率 52,9% 転移温度37℃(C→N)85℃
(N4:!I)
実施例 2
実施例1と同様にして下記化合物を得た。Yield 52.9% Transition temperature 37℃ (C→N) 85℃
(N4:!I) Example 2 The following compound was obtained in the same manner as in Example 1.
収率 50.1% 転移温度 64℃(C→N)51℃
(NII)
実施例 3
実施例1と同様にして下記化合物全書た。Yield 50.1% Transition temperature 64℃ (C→N) 51℃
(NII) Example 3 The following compounds were all prepared in the same manner as in Example 1.
収率 494% 転移温度 34℃(C−0S )78
℃(NdI)
実施例 4
実施例1と同様にして下記化合中を得た。Yield: 494% Transition temperature: 34°C (C-0S) 78
°C (NdI) Example 4 The following compound was obtained in the same manner as in Example 1.
収率 54.1% 転移温度 27℃(C−+N )9
2℃(N口I)
実施例 5
実施例1と同様にして下記化合物を得た。Yield: 54.1% Transition temperature: 27°C (C-+N)9
2°C (N port I) Example 5 The following compound was obtained in the same manner as in Example 1.
収率 55.89b 転移温度 58℃(C−4N )
89℃(Ni=fI)Yield: 55.89b Transition temperature: 58°C (C-4N)
89℃ (Ni=fI)
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5959084A JPS60204732A (en) | 1984-03-29 | 1984-03-29 | Novel phenylalkylethylenic nematic liquid crystal compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5959084A JPS60204732A (en) | 1984-03-29 | 1984-03-29 | Novel phenylalkylethylenic nematic liquid crystal compound |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60204732A true JPS60204732A (en) | 1985-10-16 |
JPH041732B2 JPH041732B2 (en) | 1992-01-14 |
Family
ID=13117595
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP5959084A Granted JPS60204732A (en) | 1984-03-29 | 1984-03-29 | Novel phenylalkylethylenic nematic liquid crystal compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60204732A (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS559012A (en) * | 1978-07-05 | 1980-01-22 | Hitachi Ltd | Liquid crystal compound |
JPS58110527A (en) * | 1981-12-18 | 1983-07-01 | エフ・ホフマン―ラ ロシユ アーゲー | Acetylene derivative |
-
1984
- 1984-03-29 JP JP5959084A patent/JPS60204732A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS559012A (en) * | 1978-07-05 | 1980-01-22 | Hitachi Ltd | Liquid crystal compound |
JPS58110527A (en) * | 1981-12-18 | 1983-07-01 | エフ・ホフマン―ラ ロシユ アーゲー | Acetylene derivative |
Also Published As
Publication number | Publication date |
---|---|
JPH041732B2 (en) | 1992-01-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4617141A (en) | Trans-4-alkyloxymethyl-1-(4'-substituted biphenylyl-4)cyclohexanes | |
US4558151A (en) | Nematic liquid crystalline compounds | |
JPS5933565B2 (en) | 1-Cyclohexyl-2-cyclohexylbiphenylethane derivative | |
JPS60155142A (en) | Novel trans-type nematic liquid crystal compound | |
JPS588023A (en) | 1,2-di-(cyclohexylphenyl)ethane derivative | |
JPS63310838A (en) | Tolan type novel liquid crystal compound | |
JPS6033411B2 (en) | 1-cyclohexyl-2-cyclohexyl phenylethane derivative | |
JPS615031A (en) | Novel trans hydrocarbon compound | |
JPS60204732A (en) | Novel phenylalkylethylenic nematic liquid crystal compound | |
US4698177A (en) | Cyclohexylcyclohexene derivatives | |
JP3944611B2 (en) | Dialkenyl biphenyl derivatives | |
JPS60152427A (en) | Novel trans-nematic liquid crystal compound | |
JPS58167535A (en) | Trans,trans-4-alkyl-4'-alkyloxymethylbicyclohexane | |
JPS5933566B2 (en) | 1,4-di-(cyclohexylethyl)biphenyl derivative | |
JPS59110631A (en) | 1,4-di-(cyclohexylethyl) biphenyl derivative | |
JPS59110630A (en) | 1-cyclohexyl-2-cyclohexylbiphenylethane derivative | |
JPS6092228A (en) | 4-halogenobiphenyl derivative consisting of four rings | |
JPS60202830A (en) | Novel phenylalkylacetylene based nematic liquid crystal compound | |
JPS61291536A (en) | Crotyloxybenzene derivative | |
JPS5910551A (en) | Novel nematic liquid crystal compound | |
JPS63152334A (en) | Tolan-type novel liquid crystal compound | |
JPH0335302B2 (en) | ||
JPS62277333A (en) | 4-substituted phenylcrotyl ether derivative | |
JPH062696B2 (en) | Tolan type new liquid crystal compound | |
JPS60204734A (en) | Novel tolan based nematic liquid crystal compound |