JPH04266836A - Terphenyl derivative, liquid crystalline composition containing the same derivative and liquid crystal display device using the same composition - Google Patents
Terphenyl derivative, liquid crystalline composition containing the same derivative and liquid crystal display device using the same compositionInfo
- Publication number
- JPH04266836A JPH04266836A JP2845291A JP2845291A JPH04266836A JP H04266836 A JPH04266836 A JP H04266836A JP 2845291 A JP2845291 A JP 2845291A JP 2845291 A JP2845291 A JP 2845291A JP H04266836 A JPH04266836 A JP H04266836A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- liquid crystalline
- formula
- compound
- crystal display
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 45
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000007788 liquid Substances 0.000 title abstract 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 6
- 239000000243 solution Substances 0.000 abstract description 5
- 239000007818 Grignard reagent Substances 0.000 abstract description 4
- 150000004795 grignard reagents Chemical class 0.000 abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 abstract description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 3
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 abstract description 3
- UCXUDHQYPZVKEG-UHFFFAOYSA-N 1-butyl-4-[2-(3-fluorophenyl)phenyl]benzene Chemical group C(CCC)C1=CC=C(C=C1)C=1C(=CC=CC=1)C1=CC(=CC=C1)F UCXUDHQYPZVKEG-UHFFFAOYSA-N 0.000 abstract description 2
- 230000005540 biological transmission Effects 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- DKCMBSJGEAEGOE-UHFFFAOYSA-N [4-(4-butylphenyl)phenyl]boronic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(B(O)O)C=C1 DKCMBSJGEAEGOE-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- IQXYRXOYBYUMLV-UHFFFAOYSA-N 1-fluoro-2-(2-phenylphenyl)benzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 IQXYRXOYBYUMLV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- -1 butyl-3”-fluoroterphenyl Chemical group 0.000 description 1
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は電気光学的表示材料とし
て用いられる新規なターフェニル誘導体及びそれを含有
する液晶組成物及びそれを用いた液晶表示素子に関する
。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel terphenyl derivative used as an electro-optical display material, a liquid crystal composition containing the same, and a liquid crystal display element using the same.
【０００２】0002
【従来の技術】液晶表示装置は液晶の持つ電気光学効果
を利用したものであり、これに用いられる液晶相にはネ
マチック相、コレステリック相、スメクチック相がある
。そして現在もっとも広く用いられる表示方式はネマチ
ック相を利用したねじれネマチック（以下ＴＮという）
型である。2. Description of the Related Art Liquid crystal display devices utilize the electro-optic effect of liquid crystals, and liquid crystal phases used therein include nematic, cholesteric, and smectic phases. Currently, the most widely used display method is twisted nematic (hereinafter referred to as TN), which uses a nematic phase.
It is a type.
【０００３】液晶表示装置は １，小型でしかも薄くできる。[0003]The liquid crystal display device is 1. Can be made small and thin.
【０００４】２，駆動電圧が低く、かつ消費電力が小さ
い。2. Low driving voltage and low power consumption.
【０００５】３，受光素子であるため長時間使用しても
目が疲れない。3. Since it is a light receiving element, the eyes will not get tired even if it is used for a long time.
【０００６】等の長所を持つことから、従来よりウォッ
チ、電卓、オーディオ機器、各種計測機、自動車のダッ
シュボード等に応用されている。特に最近ではパーソナ
ルコンピューターやワードプロセッサーのディスプレイ
さらにはカラーテレビなどの画素数の大変多い表示にも
応用されＣＲＴに代わる表示装置として注目を集めてい
る。このように液晶表示装置は多方面に応用されており
、今後さらにその応用分野は拡大していくと考えられる
。これにともない液晶材料に要求される特性も変化して
いくと思われるが、以下に示した特性は基本的なもので
必要不可欠である。
１，着色がなく、熱、光、電気的、化学的に安定である
こと。[0006] Because of these advantages, it has been applied to watches, calculators, audio equipment, various measuring instruments, automobile dashboards, etc. Particularly recently, it has been applied to displays with a large number of pixels, such as personal computers and word processors, as well as color televisions, and is attracting attention as a display device that can replace CRTs. As described above, liquid crystal display devices are being applied in many fields, and it is thought that the fields of application will further expand in the future. Along with this, the characteristics required of liquid crystal materials are expected to change, but the characteristics shown below are basic and indispensable. 1. Must be non-colored and thermally, optically, electrically and chemically stable.
【０００７】２，実用温度範囲が広いこと。2. Wide practical temperature range.
【０００８】３，電気光学的な応答速度が速いこと。3. Fast electro-optical response speed.
【０００９】４，駆動電圧が低いこと。4. Low driving voltage.
【００１０】５，電圧−光透過率特性の立ち上がりが急
峻であり、またそのしきい値電圧（以下Ｖｔｈという）
の温度依存性が小さいこと。5. The voltage-light transmittance characteristic has a steep rise, and its threshold voltage (hereinafter referred to as Vth)
temperature dependence is small.
【００１１】６，視角範囲が広いこと。6. Wide viewing angle range.
【００１２】0012
【発明が解決しようとする課題】しかしながらこれらの
特性のうち、１の特性を満足する液晶は数多く知られて
いるが２以下の特性を単一成分で満足させる液晶化合物
は知られていない。そこでこれらの特性を得るために数
種類のネマチック液晶化合物または非液晶化合物を混合
した液晶組成物を用いている。これらの特性のうちで５
の特性は表示容量の多い素子に用いられる液晶組成物に
は重要な特性となる。[Problems to be Solved by the Invention] However, although many liquid crystals are known that satisfy property 1 among these properties, no liquid crystal compound is known that satisfies property 2 or less with a single component. Therefore, in order to obtain these characteristics, a liquid crystal composition in which several types of nematic liquid crystal compounds or non-liquid crystal compounds are mixed is used. Five of these characteristics
These characteristics are important for liquid crystal compositions used in devices with a large display capacity.
【００１３】そこで本発明はこのような実状における要
請に応じるものであり、その目的は数種類のネマチック
液晶化合物または非液晶化合物に混合した場合、電圧−
光透過率特性の立ち上がりが急峻である新規な液晶化合
物を提供し、それを用いることにより大容量表示が可能
な液晶表示装置を提供することにある。[0013] The present invention has been made to meet the needs of the above-mentioned situation, and its purpose is to reduce the voltage - when mixed with several types of nematic liquid crystal compounds or non-liquid crystal compounds.
It is an object of the present invention to provide a novel liquid crystal compound whose light transmittance characteristic rises steeply, and to provide a liquid crystal display device capable of displaying a large capacity by using the novel liquid crystal compound.
【００１４】[0014]
【課題を解決するための手段】本発明は一般式[Means for Solving the Problems] The present invention is based on the general formula
【００１
５】001
5]
【化４】[C4]
【００１６】（上式中、Ｒは炭素数が１〜１０の直鎖ア
ルキル基を表す）で表されるターフェニル誘導体及びそ
れを含有する液晶組成物及びそれを用いた液晶表示素子
である。本発明化合物（１）は次の製造方法により得る
ことができる。The present invention relates to a terphenyl derivative represented by the formula (in the above formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms), a liquid crystal composition containing the same, and a liquid crystal display element using the same. The compound (1) of the present invention can be obtained by the following production method.
【００１７】[0017]
【表１】[Table 1]
【００１８】工程１）化合物（２）をテトラヒドロフラ
ン中でグリニヤール試薬とし、ほう酸トリイソプロピル
と反応させ化合物（３）を得る。Step 1) Compound (2) is converted into a Grignard reagent in tetrahydrofuran and reacted with triisopropyl borate to obtain compound (3).
【００１９】工程２）化合物（３）と化合物（４）を炭
酸ナトリウム水溶液、ベンゼン、エタノールの混合溶媒
中で、テトラキストリフェニルフォスフィンパラジウム
の存在下で反応させ化合物（１）を得る。Step 2) Compound (3) and compound (4) are reacted in a mixed solvent of an aqueous sodium carbonate solution, benzene and ethanol in the presence of tetrakistriphenylphosphine palladium to obtain compound (1).
【００２０】本発明のターフェニル誘導体を混合する場
合にベースとなる液晶組成物の成分としては次に示した
化合物があげられるが、これに限定されることなく、従
来のすべての液晶化合物またはその類似化合物と良好な
相溶性を有し、得られた液晶組成物は電圧−光透過率特
性の立ち上がりが急峻であるという特徴を有する。When the terphenyl derivative of the present invention is mixed, the components of the base liquid crystal composition include the following compounds, but are not limited thereto, and all conventional liquid crystal compounds or their It has good compatibility with similar compounds, and the resulting liquid crystal composition is characterized by a steep rise in voltage-light transmittance characteristics.
【００２１】[0021]
【表２】[Table 2]
【００２２】（ここでＲおよびＲ’はアルキル基、アル
コキシ基、アルコキシメチレン基、ニトリル基、または
フルオロ基を表し、フェニレン基は２または３位にハロ
ゲン置換基を有してもよく、シクロヘキサン環はトラン
ス配置である。）また、この液晶組成物に本発明の化合
物を混合できる割合は１〜５０重量パーセントであるが
、低温領域での結晶析出を考慮した場合には３〜３０重
量パーセントの範囲が特に好ましい。(Here, R and R' represent an alkyl group, an alkoxy group, an alkoxymethylene group, a nitrile group, or a fluoro group, and the phenylene group may have a halogen substituent at the 2- or 3-position, and a cyclohexane ring is a trans configuration.) Furthermore, the proportion of the compound of the present invention that can be mixed into this liquid crystal composition is 1 to 50% by weight, but when considering crystal precipitation in a low temperature region, it is 3 to 30% by weight. The range is particularly preferred.
【００２３】本発明の化合物を少なくとも一種類含有す
る液晶組成物を使用した液晶表示装置は時分割駆動方式
を用いた液晶表示装置に好適であり、特にＴＮ型及びＳ
ＴＮ型の液晶表示素子において高時分割駆動が可能であ
る。A liquid crystal display device using a liquid crystal composition containing at least one compound of the present invention is suitable for a liquid crystal display device using a time-division driving method, and is particularly suitable for TN type and S type liquid crystal display devices.
High time division driving is possible in a TN type liquid crystal display element.
【００２４】[0024]
【実施例】以下、実施例により本発明ををさらに詳しく
説明する。[Examples] The present invention will be explained in more detail with reference to Examples below.
【００２５】（実施例１）〔化合物（１）の合成〕４−
ブチル−３”−フルオロターフェニルの製造工程１）窒
素雰囲気中、フラスコへマグネシウム１．８ｇを入れ、
そこへテトラヒドロフラン１００ｍｌへ４−ブチル−４
”−ブロモビフェニル２０ｇを溶かした溶液を滴下した
。滴下終了後室温で一晩攪拌し、グリニヤール試薬を作
成した。ほう酸トリイソプロピル２４ｇをテトラヒドロ
フラン７．３ｍｌに溶解し、その中へグリニヤール試薬
を室温で滴下した。滴下終了後室温で一晩攪拌した。そ
の後１０％塩酸４４ｍｌを加え１時間攪拌した。クロロ
ホルムで抽出後、水で３回洗浄しクロロホルムを留去し
た。得られた残さをアセトン中より再結晶し、４−ブチ
ル−４’−ビフェニルほう酸６．８ｇを得た。(Example 1) [Synthesis of compound (1)] 4-
Production process of butyl-3”-fluoroterphenyl 1) In a nitrogen atmosphere, put 1.8 g of magnesium into a flask,
Then add 4-butyl-4 to 100 ml of tetrahydrofuran.
A solution in which 20 g of bromobiphenyl was dissolved was added dropwise. After the addition was completed, the Grignard reagent was prepared by stirring overnight at room temperature. 24 g of triisopropyl borate was dissolved in 7.3 ml of tetrahydrofuran, and the Grignard reagent was added therein at room temperature. After dropping, it was stirred at room temperature overnight. Then, 44 ml of 10% hydrochloric acid was added and stirred for 1 hour. After extraction with chloroform, it was washed three times with water and chloroform was distilled off. The resulting residue was extracted from acetone. Recrystallization yielded 6.8 g of 4-butyl-4'-biphenylboronic acid.
【００２６】工程２）窒素雰囲気中、１−ブロモ−３−
フルオロベンゼン１．４ｇ、テトラキストリフェニルフ
ォスフィンパラジウム０．４ｇ、ベンゼン１７ｍｌ、２
Ｍ炭酸ナトリウム水溶液１４ｍｌの混合液中へ、４−ブ
チル−４’−ビフェニルほう酸２．３ｇをエタノール４
５ｍｌとベンゼン１５ｍｌの混合溶媒に溶かした溶液を
室温で適下した。その後５時間還流後、室温に冷却し、
反応液をクロロホルムで抽出し、水洗を３回行いクロロ
ホルムを留去した。得られた残さをクロロホルム、アセ
トンの混合溶媒中より再結晶をし、４−ブチル−３”−
フルオロターフェニル０．４ｇを得た。この化合物の結
晶相−スメクチック液晶相転移点（以下Ｃ−Ｓｍ点とい
う）は９３．０℃であり、スメクチック液晶相−等方性
液体相（以下Ｓｍ−Ｉ点という）は１６０．７℃であっ
た。Step 2) In a nitrogen atmosphere, 1-bromo-3-
1.4 g of fluorobenzene, 0.4 g of tetrakistriphenylphosphine palladium, 17 ml of benzene, 2
Into a mixture of 14 ml of M sodium carbonate aqueous solution, 2.3 g of 4-butyl-4'-biphenylboronic acid was added to 4 ml of ethanol.
A solution of 5 ml of a mixed solvent of benzene and 15 ml of benzene was dropped at room temperature. After refluxing for 5 hours, it was cooled to room temperature.
The reaction solution was extracted with chloroform, washed with water three times, and the chloroform was distilled off. The obtained residue was recrystallized from a mixed solvent of chloroform and acetone to give 4-butyl-3''-
0.4 g of fluoroterphenyl was obtained. The crystal phase-smectic liquid crystal phase transition point (hereinafter referred to as C-Sm point) of this compound is 93.0°C, and the smectic liquid crystal phase-isotropic liquid phase (hereinafter referred to as Sm-I point) is 160.7°C. there were.
【００２７】同様の方法で以下の化合物を合成した。
４−メチル−３”−フルオロターフェニル４−エチル−
３”−フルオロターフェニル４−プロピル−３”−フル
オロターフェニル４−ペンチル−３”−フルオロターフ
ェニル４−ヘキシル−３”−フルオロターフェニル４−
ヘプチル−３”−フルオロターフェニル４−オクチル−
３”−フルオロターフェニル４−ノニル−３”−フルオ
ロターフェニル４−デシル−３”−フルオロターフェニ
ル（実施例２）〔液晶組成物〕
市販の混合液晶ＺＬＩ−１５６５（メルク社製品、Ｎ−
Ｉ点８９．３℃）をベース液晶とし、現在一般的にＮ−
Ｉ点を高くする目的で使用されている４−ペンチル−４
”−シアノターフェニルと本発明化合物である実施例１
の４−ブチル−３”−フルオロターフェニルの液晶組成
物を作った。The following compounds were synthesized in a similar manner. 4-Methyl-3”-fluoroterphenyl 4-ethyl-
3"-fluoroterphenyl 4-propyl-3"-fluoroterphenyl 4-pentyl-3"-fluoroterphenyl 4-hexyl-3"-fluoroterphenyl 4-
heptyl-3”-fluoroterphenyl 4-octyl-
3"-fluoroterphenyl 4-nonyl-3"-fluoroterphenyl 4-decyl-3"-fluoroterphenyl (Example 2) [Liquid crystal composition] Commercially available mixed liquid crystal ZLI-1565 (Merck product, N-
I point (89.3℃) is used as the base liquid crystal, and currently N-
4-pentyl-4, which is used to increase the I point
”-cyanoterphenyl and the compound of the present invention Example 1
A liquid crystal composition of 4-butyl-3''-fluoroterphenyl was prepared.
【００２８】[0028]
【表３】[Table 3]
【００２９】組成物ａおよびｂのＮ−Ｉ点、複屈折（以
下Δｎという）を測定した。その結果は以下のとおりで
ある。The N-I point and birefringence (hereinafter referred to as Δn) of compositions a and b were measured. The results are as follows.
【００３０】[0030]
【表４】[Table 4]
【００３１】（実施例３）〔液晶表示素子〕図１に示す
ようにガラス基板１及び２の上に透明電極膜（例えばＩ
ＴＯ膜）からなる電極３を形成し、この上にポリイミド
等よりなる配向膜を塗布する。次ににラビングして配向
制御層４を形成し、さらにガラス基板１及び２をシール
剤６を介して対向配置し、ガラス基板間に実施例２で作
った液晶組成ａおよびｂをそれぞれ注入し、基板１及び
２の外面に偏光板を貼り付けてＴＮ型の液晶表示セルＡ
およびＢを作成した。なお、セルギャプは８μｍとした
。(Example 3) [Liquid crystal display element] As shown in FIG. 1, transparent electrode films (for example, I
An electrode 3 made of (TO film) is formed, and an alignment film made of polyimide or the like is applied thereon. Next, the alignment control layer 4 is formed by rubbing, and the glass substrates 1 and 2 are placed facing each other with a sealant 6 in between, and the liquid crystal compositions a and b prepared in Example 2 are injected between the glass substrates, respectively. , polarizing plates are pasted on the outer surfaces of substrates 1 and 2 to form a TN type liquid crystal display cell A.
and B were created. Note that the cell gap was 8 μm.
【００３２】このようにして作成した液晶表示セルを交
流スタテック駆動を用い、２０℃で電圧−光透過性の視
角依存性（以下αという）、急峻性（以下βという）、
Ｖｔｈを測定した。なお、α、β、Ｖｔｈ、Ｖｓａｔは
次式で定義した。The thus produced liquid crystal display cell was subjected to AC static driving to determine the voltage-light transmittance viewing angle dependence (hereinafter referred to as α), steepness (hereinafter referred to as β), and
Vth was measured. Note that α, β, Vth, and Vsat were defined by the following equations.
【００３３】[0033]
【数１】[Math 1]
【００３４】測定の結果は以下のとおりであった。The results of the measurement were as follows.
【００３５】[0035]
【表５】[Table 5]
【００３６】なお、上記の実施例においてはＴＮ型の液
晶表示セルを用いたが、ＳＴＮ型の表示セルを用いた場
合にも同様な効果が得られた。Although a TN type liquid crystal display cell was used in the above embodiment, similar effects were obtained when an STN type display cell was used.
【００３７】[0037]
【発明の効果】以上述べた如く、本発明の化合物は一般
的な液晶混合物に混合することにより、電気光学特性（
α値、β値）が良い液晶組成物が得られる。これらの点
で本発明は、現在表示装置の主流となっているＳＴＮ型
表示の液晶組成物の基本的成分として極めて有効である
。Effects of the Invention As described above, the compound of the present invention can improve electro-optical properties (
A liquid crystal composition with good α value and β value can be obtained. In these respects, the present invention is extremely effective as a basic component of liquid crystal compositions for STN type displays, which are currently the mainstream of display devices.
【図１】本発明の実施例で作成した液晶表示セルを示す
図。FIG. 1 is a diagram showing a liquid crystal display cell prepared in an example of the present invention.
１．２．ガラス基板 ３．透明電極 ４．配向制御層 ５．偏光板 ６．シール剤 1.2. glass substrate 3. transparent electrode 4. Orientation control layer 5. Polarizer 6. sealant
Claims (3)
す）で表されることを特徴とするターフェニル誘導体。1. A terphenyl derivative represented by the general formula: [In the above formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms].
す）で表されるターフェニル誘導体の少なくとも１種類
を含有することを特徴とする液晶組成物。[Claim 2] It is characterized by containing at least one kind of terphenyl derivative represented by the general formula [Formula 2] (in the above formula, R represents a straight-chain alkyl group having 1 to 10 carbon atoms). liquid crystal composition.
す）で表されるターフェニル誘導体の少なくとも１種類
を含有する液晶組成物を用いたことを特徴とする液晶表
示素子。3. A liquid crystal composition containing at least one type of terphenyl derivative represented by the general formula [Formula 3] (wherein R represents a linear alkyl group having 1 to 10 carbon atoms) A liquid crystal display element characterized in that it is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2845291A JPH04266836A (en) | 1991-02-22 | 1991-02-22 | Terphenyl derivative, liquid crystalline composition containing the same derivative and liquid crystal display device using the same composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2845291A JPH04266836A (en) | 1991-02-22 | 1991-02-22 | Terphenyl derivative, liquid crystalline composition containing the same derivative and liquid crystal display device using the same composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04266836A true JPH04266836A (en) | 1992-09-22 |
Family
ID=12249061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2845291A Pending JPH04266836A (en) | 1991-02-22 | 1991-02-22 | Terphenyl derivative, liquid crystalline composition containing the same derivative and liquid crystal display device using the same composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04266836A (en) |
-
1991
- 1991-02-22 JP JP2845291A patent/JPH04266836A/en active Pending
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