JPH0959219A - Tolan compound and liquid crystal composition containing the same - Google Patents
Tolan compound and liquid crystal composition containing the sameInfo
- Publication number
- JPH0959219A JPH0959219A JP7216027A JP21602795A JPH0959219A JP H0959219 A JPH0959219 A JP H0959219A JP 7216027 A JP7216027 A JP 7216027A JP 21602795 A JP21602795 A JP 21602795A JP H0959219 A JPH0959219 A JP H0959219A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- crystal composition
- formula
- tolan
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- -1 Tolan compound Chemical class 0.000 title claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 32
- 239000000463 material Substances 0.000 abstract description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000007704 transition Effects 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 2
- ORFXQKRDHJTVCW-UHFFFAOYSA-N [4-[4-[2-(4-ethylphenyl)ethynyl]phenyl]phenyl] 4-butylcyclohexane-1-carboxylate Chemical group C1CC(CCCC)CCC1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C#CC=2C=CC(CC)=CC=2)C=C1 ORFXQKRDHJTVCW-UHFFFAOYSA-N 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
- 230000000007 visual effect Effects 0.000 abstract 1
- 238000000862 absorption spectrum Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- ZNTJVJSUNSUMPP-UHFFFAOYSA-N 1-ethyl-4-ethynylbenzene Chemical group CCC1=CC=C(C#C)C=C1 ZNTJVJSUNSUMPP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- ZGOWIHIGUHWAMQ-UHFFFAOYSA-N 2-(4-bromophenyl)phenol Chemical compound OC1=CC=CC=C1C1=CC=C(Br)C=C1 ZGOWIHIGUHWAMQ-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 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 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QXSWHQGIEKUBAS-UHFFFAOYSA-N 1-ethynyl-4-fluorobenzene Chemical group FC1=CC=C(C#C)C=C1 QXSWHQGIEKUBAS-UHFFFAOYSA-N 0.000 description 1
- UVFFOABHOIMLNB-UHFFFAOYSA-N 1-ethynyl-4-propylbenzene Chemical group CCCC1=CC=C(C#C)C=C1 UVFFOABHOIMLNB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZHJCVLQOKPGYDJ-MGCOHNPYSA-N CCCC[C@H]1CC[C@@H](CC1)C(Cl)=O Chemical compound CCCC[C@H]1CC[C@@H](CC1)C(Cl)=O ZHJCVLQOKPGYDJ-MGCOHNPYSA-N 0.000 description 1
- BALGERHMIXFENA-MGCOHNPYSA-N CCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCC[C@H]1CC[C@H](C(O)=O)CC1 BALGERHMIXFENA-MGCOHNPYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- FFFMSANAQQVUJA-UHFFFAOYSA-N but-1-ynylbenzene Chemical group CCC#CC1=CC=CC=C1 FFFMSANAQQVUJA-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は液晶材料として有用なト
ラン化合物に関し、さらにこのトラン化合物を含有する
液晶組成物に関するものである。FIELD OF THE INVENTION The present invention relates to a tolan compound useful as a liquid crystal material, and further to a liquid crystal composition containing the tolan compound.
【０００２】[0002]
【従来の技術】液晶表示装置は、時計、電卓をはじめワ
ープロ、テレビ等に広く利用されている。これらの液晶
表示装置の中で特に多く使用されているのは、液晶材料
の光学的異方性および誘電率異方性を利用した液晶表示
装置である。2. Description of the Related Art Liquid crystal display devices are widely used in clocks, calculators, word processors, televisions, and the like. Among these liquid crystal display devices, a liquid crystal display device that utilizes the optical anisotropy and the dielectric anisotropy of a liquid crystal material is particularly frequently used.
【０００３】液晶表示装置に用いられる液晶材料に要求
される特性としては、液晶温度範囲が広いこと、電気光
学的に速い応答速度を得るために粘度が小さいこと、広
い視野角範囲、高いコントラストを得るために適切な複
屈折（△ｎ）をもつこと、低い駆動電圧を得るために誘
電率異方性（△ε）が大きいこと、化学的および光学的
に安定であることなどが挙げられる。The characteristics required of a liquid crystal material used in a liquid crystal display device include a wide liquid crystal temperature range, a small viscosity for obtaining a high response speed electro-optically, a wide viewing angle range, and a high contrast. It is necessary to have an appropriate birefringence (△ n) for obtaining the same, to have a large dielectric anisotropy (△ ε) for obtaining a low driving voltage, and to be chemically and optically stable.
【０００４】実用されている液晶組成物は通常、室温付
近に液晶相を有する化合物と、室温より高い温度領域に
液晶相を有する化合物とを混合して調整される。液晶表
示装置が屋外で使用し得る為には−４０℃〜９０℃の温
度範囲で安定に存在しなければならず、また誘電率異方
性、屈折率異方性の温度依存性を考慮すると、Ｎ−Ｉ点
（ネマティック−等方相転移温度）付近では急激な変化
が起こるので、Ｎ−Ｉ点の高い液晶材料が必要となる。[0004] A practically used liquid crystal composition is usually prepared by mixing a compound having a liquid crystal phase near room temperature and a compound having a liquid crystal phase in a temperature range higher than room temperature. In order for the liquid crystal display device to be used outdoors, it must exist stably in the temperature range of −40 ° C. to 90 ° C. In addition, considering the temperature dependence of dielectric anisotropy and refractive index anisotropy. , A sharp change occurs near the NI point (nematic-isotropic phase transition temperature), so that a liquid crystal material having a high NI point is required.
【０００５】また、広視野角、高コントラストを得るた
めには、液晶層のリターデーション△ｎ・ｄ（△ｎは液
晶材料の複屈折、ｄは液晶層の厚み）を最適化する必要
がある。しかし、実用に使用される液晶表示装置では液
晶層の厚みｄが、ある限定された範囲で設定されてお
り、かつ応答速度を速くすることが要求されているため
に、液晶層の厚みｄは薄くなる傾向が強まっている。よ
って、複屈折△ｎが大きな液晶材料が必要とされてい
る。In order to obtain a wide viewing angle and a high contrast, it is necessary to optimize the retardation Δn · d (Δn is the birefringence of the liquid crystal material and d is the thickness of the liquid crystal layer) of the liquid crystal layer. . However, in a liquid crystal display device used for practical use, the thickness d of the liquid crystal layer is set within a certain limited range, and it is required to increase the response speed. The tendency to become thinner is increasing. Therefore, a liquid crystal material having a large birefringence Δn is required.
【０００６】これまで、種々の液晶化合物が開発され、
使用されているが、以上のような特性を全て満足する単
一の液晶化合物は未だに見い出されていない。そのため
にいろいろな特性をもった数種の液晶化合物を混合した
り、あるいは非液晶化合物を混合したりして実用に供し
ているのが現状であるが、やはり、充分満足できるもの
ではない。Until now, various liquid crystal compounds have been developed,
Although used, a single liquid crystal compound satisfying all the above characteristics has not been found yet. Therefore, at present, several kinds of liquid crystal compounds having various characteristics are mixed or non-liquid crystal compounds are mixed for practical use, but it is still not sufficiently satisfactory.
【０００７】この様に混合して用いられるトラン系の化
合物では、４−アルキル−４’−アルコキシトラン（独
国特許第２２２６３７６号）、４−アルキル−４’−フ
ルオロトラン（特開昭６１−２６００３１号）等が知ら
れているが、充分特性を満足できるとはいえなかった。Among the tolan-based compounds used in such a mixture, 4-alkyl-4'-alkoxytran (German Patent No. 2226376) and 4-alkyl-4'-fluorotolan (JP-A-61-1 No. 260031) is known, but it cannot be said that the characteristics can be sufficiently satisfied.
【０００８】[0008]
【発明が解決しようとする課題】以上示したように、こ
れまで、液晶組成物については種々検討されているが、
未だ完全と言われるものは見いだされていない。また、
液晶組成物に用いられる化合物は、いずれもその特性に
一長一短があり、さらに液晶表示装置によって、前記要
求される特性の度合いも異なるため、目的に応じた特性
を与える新たな液晶化合物および、液晶添加物の出現が
待ち望まれている。そこで本発明の目的は、液晶組成物
に混合することによって、液晶組成物のＮ−Ｉ点を高く
し、複屈折△ｎを大きくすることのできる新規なトラン
化合物を提供することである。As described above, various studies have been made on liquid crystal compositions.
Nothing has been found to be perfect yet. Also,
Each of the compounds used in the liquid crystal composition has advantages and disadvantages in characteristics, and the degree of the required characteristics varies depending on the liquid crystal display device. The emergence of things is awaited. Therefore, an object of the present invention is to provide a novel tolan compound capable of increasing the NI point and increasing the birefringence Δn of the liquid crystal composition by mixing with the liquid crystal composition.
【０００９】[0009]
【課題を解決するための手段】本発明のトラン化合物
は、下記一般式（Ｉ）で表されるものである。The tol compound of the present invention is represented by the following general formula (I).
【００１０】[0010]
【化２】 Embedded image
【００１１】（ただし、Ｒは水素原子または炭素原子数
１〜１０のアルキル基を示し、Ｘはハロゲン原子，炭素
原子数１〜１０のアルキル基または炭素原子数１〜１０
のアルコキシ基を示し、Ｙは水素原子またはハロゲン原
子を示し、ｍ，ｎはそれぞれ独立に０または１であり、
ｍ＋ｎ＝１であるものとする。）(Wherein R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, X represents a halogen atom, an alkyl group having 1 to 10 carbon atoms or 1 to 10 carbon atoms).
An alkoxy group, Y is a hydrogen atom or a halogen atom, m and n are each independently 0 or 1.
It is assumed that m + n = 1. )
【００１２】また、本発明の液晶組成物は、一般式
（Ｉ）で表されるトラン化合物を少なくとも一種含有す
るものである。The liquid crystal composition of the present invention contains at least one tolan compound represented by the general formula (I).
【００１３】本発明のトラン化合物において置換基とし
て与えられているハロゲン原子は、塩素原子、あるいは
臭素原子を用いたものでもよいが、粘度及び比抵抗の観
点からフッ素原子のものが好ましい。The halogen atom provided as a substituent in the tolan compound of the present invention may be a chlorine atom or a bromine atom, but a fluorine atom is preferable from the viewpoint of viscosity and specific resistance.
【００１４】本発明のトラン化合物の製造方法につい
て、化３に例をあげて説明する。なお式中Ｒ，Ｘ，Ｙ，
ｍ，ｎは前記した意味を示す。まず、酸クロライド
（ａ）と置換フェノール（ｂ）とをピリジン等の不活性
有機溶媒中で反応させた後、反応混合物を再結晶、水
洗、乾燥させ、エステル化合物（ｃ）を作製する。次に
このエステル化合物（ｃ）とフェニルアセチレン（ｄ）
を、トリエチルアミン等の存在下にて反応させ、水洗、
乾燥、再結晶することにより一般式（Ｉ）で表されるト
ラン化合物を得ることができる。The method for producing the tolan compound of the present invention will be described with reference to Chemical formula 3. In the formula, R, X, Y,
m and n have the above-mentioned meanings. First, the acid chloride (a) and the substituted phenol (b) are reacted in an inert organic solvent such as pyridine, and then the reaction mixture is recrystallized, washed with water and dried to prepare an ester compound (c). Next, this ester compound (c) and phenylacetylene (d)
Are reacted in the presence of triethylamine and the like, washed with water,
The tolan compound represented by the general formula (I) can be obtained by drying and recrystallization.
【００１５】[0015]
【化３】 Embedded image
【００１６】本発明のトラン化合物は、液晶組成物に混
合することによって、液晶組成物のＮ−Ｉ点を高くし、
複屈折△ｎを大きくすることのできる優れた化合物であ
る。The tolan compound of the present invention is mixed with a liquid crystal composition to increase the NI point of the liquid crystal composition,
It is an excellent compound that can increase the birefringence Δn.
【００１７】本発明のトラン化合物は多くの液晶化合物
と混合し、液晶組成物を製造することができる。本発明
のトラン化合物と混合可能な液晶化合物としてはエステ
ル系、シクロヘキシルフェニル系、ビフェニル系、ピリ
ミジン系、ジオキサン系、トラン系などが挙げられる。
更に、これらの液晶化合物を複数混合したものに本発明
のトラン化合物を混合して用いることもできる。The tolan compound of the present invention can be mixed with many liquid crystal compounds to produce a liquid crystal composition. Examples of the liquid crystal compound that can be mixed with the tolan compound of the present invention include ester, cyclohexylphenyl, biphenyl, pyrimidine, dioxane, and tolan compounds.
Further, a mixture of a plurality of these liquid crystal compounds may be mixed with the tolan compound of the present invention.
【００１８】本発明のトラン化合物の配合量は、他の液
晶化合物の種類、配合比等により、一概に決められるも
のではないが、一般的には、１ないし３０重量％、好ま
しくは３ないし１５重量％である。The compounding amount of the tolan compound of the present invention is not generally determined by the kind and compounding ratio of other liquid crystal compounds, but is generally 1 to 30% by weight, preferably 3 to 15%. % By weight.
【００１９】[0019]
【実施例】以下、実施例を用いて本発明を具体的に説明
するが、本発明はこれら実施例に何ら限定されるもので
はない。また、本実施例におけるしきい値電圧Ｖthは、
液晶組成物をセル厚９μｍのＴＮ型液晶表示装置に搭載
して測定した値である。The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. The threshold voltage Vth in this embodiment is
It is a value measured by mounting the liquid crystal composition on a TN type liquid crystal display device having a cell thickness of 9 μm.
【００２０】（実施例１）４−ブロモフェニルフェノー
ル２０ｇ、ジメチルホルムアミド１５０ｍｌ、ピリジン
６ｇを溶解し、市販のトランス−４−ｎ−ブチルシクロ
ヘキサンカルボン酸クロライド１５ｇを滴下し、加熱、
撹拌した。その後、反応物を水中に流入し、結晶を析出
させ、濾別した。希塩酸、水で洗浄し、真空乾燥後、酢
酸エチル、メタノールの混合溶媒にて再結晶させ、トラ
ンス−４−ｎ−ブチルシクロヘキサンカルボン酸−４−
ブロモ−４’−ビフェニルエステル２０ｇを得た。これ
に４−エチルフェニルアセチレン７ｇ、ビス（トリフェ
ニルフォスフィン）パラジウム（II）クロライド０．０
３ｇ、ヨウ化銅０．０４ｇ、トリフェニルフォスフィン
０．３ｇ、トリエチルアミン１００ｍｌを加え、加熱、
撹拌した。反応物を水に流入して、塩酸で中和し、結晶
を析出させる。結晶を濾別後、水洗し、真空乾燥後、酢
酸エチルとメタノールの混合溶媒で再結晶を行い、化４
記載の化合物１２．５ｇを得た。この化合物はネマティ
ック液晶相を有し、Ｃ−Ｎ点（結晶−ネマティック相転
移温度）が２１３℃、Ｎ−Ｉ点が２２６℃であった。ま
た、この化合物の赤外線吸収スペクトルを図１に示す。(Example 1) 20 g of 4-bromophenylphenol, 150 ml of dimethylformamide and 6 g of pyridine were dissolved, 15 g of commercially available trans-4-n-butylcyclohexanecarboxylic acid chloride was added dropwise, and the mixture was heated,
It was stirred. Thereafter, the reactant was poured into water to precipitate crystals, which were separated by filtration. The extract was washed with diluted hydrochloric acid and water, dried under vacuum, recrystallized with a mixed solvent of ethyl acetate and methanol, and trans-4-n-butylcyclohexanecarboxylic acid-4-
20 g of bromo-4'-biphenyl ester was obtained. To this, 7 g of 4-ethylphenylacetylene, 0.0 of bis (triphenylphosphine) palladium (II) chloride
Add 3 g, copper iodide 0.04 g, triphenylphosphine 0.3 g, and triethylamine 100 ml, and heat.
It was stirred. The reaction is poured into water and neutralized with hydrochloric acid to precipitate crystals. The crystals were separated by filtration, washed with water, dried in vacuum, and recrystallized with a mixed solvent of ethyl acetate and methanol to give
12.5 g of the stated compound are obtained. This compound had a nematic liquid crystal phase and had a C-N point (crystal-nematic phase transition temperature) of 213 ° C and an NI point of 226 ° C. FIG. 1 shows the infrared absorption spectrum of this compound.
【００２１】[0021]
【化４】 Embedded image
【００２２】（実施例２）４−エチルフェニルアセチレ
ン７ｇの代わりに４−ｎ−プロピルフェニルアセチレン
８ｇを用いる以外は、実施例１と同様の方法で、化５記
載の化合物１３ｇを得た。この化合物はネマティック液
晶相を有し、Ｃ−Ｎ点が２０９℃、Ｎ−Ｉ点が２２４℃
であった。また、この化合物の赤外線吸収スペクトルを
図２に示す。Example 2 13 g of the compound represented by Chemical formula 5 was obtained in the same manner as in Example 1 except that 8 g of 4-n-propylphenylacetylene was used instead of 7 g of 4-ethylphenylacetylene. This compound has a nematic liquid crystal phase and has a C-N point of 209 ° C. and an NI point of 224 ° C.
Met. The infrared absorption spectrum of this compound is shown in FIG.
【００２３】[0023]
【化５】 Embedded image
【００２４】（実施例３）４−エチルフェニルアセチレ
ン７ｇの代わりに４−フルオロフェニルアセチレン６ｇ
を用いる以外は、実施例１と同様の方法で、化６記載の
化合物１２ｇを得た。この化合物はネマティック液晶相
を有し、Ｃ−Ｎ点が２０９℃、Ｎ−Ｉ点が２３７℃であ
った。また、この化合物の赤外線吸収スペクトルを図３
に示す。Example 3 6 g of 4-fluorophenylacetylene instead of 7 g of 4-ethylphenylacetylene
12 g of the compound described in Chemical formula 6 was obtained by the same method as in Example 1 except that was used. This compound had a nematic liquid crystal phase and had a C-N point of 209 ° C. and an NI point of 237 ° C. In addition, the infrared absorption spectrum of this compound is shown in FIG.
Shown in
【００２５】[0025]
【化６】 [Chemical 6]
【００２６】（実施例４）４−ブロモフェニルフェノー
ル２０ｇの代わりに４−ブロモフェノール１４ｇ、４−
エチルフェニルアセチレン７ｇの代わりに４−ｎ−ヘプ
チルビフェニルアセチレン１１ｇを用いる以外は、実施
例１と同様の方法で、化７記載の化合物１４ｇを得た。
この化合物はネマティック液晶相を有し、Ｃ−Ｎ点が２
０７℃、Ｎ−Ｉ点が３０２℃であった。また、この化合
物の赤外線吸収スペクトルを図４に示す。Example 4 14 g of 4-bromophenol, 4-g instead of 20 g of 4-bromophenylphenol
14 g of the compound described in Chemical formula 7 was obtained in the same manner as in Example 1 except that 11 g of 4-n-heptylbiphenylacetylene was used instead of 7 g of ethylphenylacetylene.
This compound has a nematic liquid crystal phase and has a C-N point of 2
The temperature was 07 ° C and the NI point was 302 ° C. FIG. 4 shows the infrared absorption spectrum of this compound.
【００２７】[0027]
【化７】 [Chemical 7]
【００２８】（実施例５）市販のネマティック液晶組成
物ＺＬＩ−１１３２（メルク社製）９５重量部に、実施
例１で製造した本発明のトラン化合物を５重量部加え、
液晶組成物を作製した。その液晶組成物の特性を表１に
示す。Example 5 To 95 parts by weight of a commercially available nematic liquid crystal composition ZLI-1132 (manufactured by Merck Ltd.), 5 parts by weight of the tolan compound of the present invention prepared in Example 1 was added,
A liquid crystal composition was prepared. The characteristics of the liquid crystal composition are shown in Table 1.
【００２９】ここで、ＺＬＩ−１１３２のみからなる液
晶組成物の特性は、Ｎ−Ｉ点７２℃、Δｎ０．１３８、
粘度２７．９ｃＰ、Ｖth１．８３Ｖであった。The characteristics of the liquid crystal composition consisting of ZLI-1132 are as follows: NI point 72 ° C., Δn 0.138,
The viscosity was 27.9 cP and Vth was 1.83V.
【００３０】[0030]
【表１】 [Table 1]
【００３１】（実施例６〜８）実施例５と同様にＺＬＩ
−１１３２の９５重量部に、実施例２〜４で製造したト
ラン化合物を５重量部加え、液晶組成物を作製した。そ
の液晶組成物の特性を表１に併せて示す。(Embodiments 6 to 8) ZLI as in Embodiment 5
A liquid crystal composition was prepared by adding 5 parts by weight of the tolan compound prepared in Examples 2 to 4 to 95 parts by weight of -1132. The properties of the liquid crystal composition are also shown in Table 1.
【００３２】表１から明らかなように、本発明のトラン
化合物は、少量の添加により、それを含有する液晶組成
物のＮ−Ｉ点を非常に高くし、複屈折△ｎを非常に大き
くすることができる。As is apparent from Table 1, the addition of a small amount of the tolan compound of the present invention makes the liquid crystal composition containing it to have a very high NI point and a very large birefringence Δn. be able to.
【００３３】[0033]
【発明の効果】本発明のトラン化合物は、液晶組成物に
少量混合することによって、液晶組成物のＮ−Ｉ点を高
くし、また複屈折を大きくすることができる。そのた
め、本発明のトラン化合物を含有する液晶組成物は液晶
材料として優れた特性を有し、またこの液晶組成物を搭
載した液晶表示装置は、温度範囲が広く、広い視野角を
持つ。さらに、本発明のトラン化合物は種々の化合物と
の充分な相互溶解性が得られ、液晶組成物の構成物質と
して多くの液晶材料と組み合わせて使用することがで
き、液晶組成物の特性改良に有用なものである。INDUSTRIAL APPLICABILITY By adding a small amount of the tolan compound of the present invention to a liquid crystal composition, the NI point of the liquid crystal composition can be increased and the birefringence can be increased. Therefore, the liquid crystal composition containing the tolan compound of the present invention has excellent characteristics as a liquid crystal material, and a liquid crystal display device equipped with the liquid crystal composition has a wide temperature range and a wide viewing angle. Further, the tolan compound of the present invention has sufficient mutual solubility with various compounds and can be used in combination with many liquid crystal materials as a constituent of the liquid crystal composition, and is useful for improving the characteristics of the liquid crystal composition. It is something.
【図１】本発明のトラン化合物の赤外線吸収スペクトル
を表す図である。FIG. 1 is a diagram showing an infrared absorption spectrum of a tolan compound of the present invention.
【図２】本発明のトラン化合物の赤外線吸収スペクトル
を表す図である。FIG. 2 is a diagram showing an infrared absorption spectrum of a tolan compound of the present invention.
【図３】本発明のトラン化合物の赤外線吸収スペクトル
を表す図である。FIG. 3 is a diagram showing an infrared absorption spectrum of the tolan compound of the present invention.
【図４】本発明のトラン化合物の赤外線吸収スペクトル
を表す図である。FIG. 4 is a view showing an infrared absorption spectrum of the tolan compound of the present invention.
Claims (2)
ルキル基を示し、Ｘはハロゲン原子，炭素原子数１〜１
０のアルキル基または炭素原子数１〜１０のアルコキシ
基を示し、Ｙは水素原子またはハロゲン原子を示し、
ｍ，ｎはそれぞれ独立に０または１であり、ｍ＋ｎ＝１
であるものとする。）1. A tolan compound represented by the general formula (I). Embedded image (However, R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, X represents a halogen atom, or 1 to 1 carbon atoms.
0 represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms, Y represents a hydrogen atom or a halogen atom,
m and n are independently 0 or 1, and m + n = 1
It is assumed that )
も一種含有する液晶組成物。2. A liquid crystal composition comprising at least one tolan compound according to claim 1.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21602795A JP4034835B2 (en) | 1995-08-24 | 1995-08-24 | Tolan compound and liquid crystal composition containing the same |
| US08/628,028 US5656198A (en) | 1995-04-07 | 1996-04-04 | Tolan compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21602795A JP4034835B2 (en) | 1995-08-24 | 1995-08-24 | Tolan compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0959219A true JPH0959219A (en) | 1997-03-04 |
| JP4034835B2 JP4034835B2 (en) | 2008-01-16 |
Family
ID=16682156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21602795A Expired - Fee Related JP4034835B2 (en) | 1995-04-07 | 1995-08-24 | Tolan compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4034835B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5972244A (en) * | 1997-01-14 | 1999-10-26 | Citizen Watch Co., Ltd. | Tolan compound and liquid crystal composition containing the same |
| JPWO2023127537A1 (en) * | 2021-12-28 | 2023-07-06 |
-
1995
- 1995-08-24 JP JP21602795A patent/JP4034835B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5972244A (en) * | 1997-01-14 | 1999-10-26 | Citizen Watch Co., Ltd. | Tolan compound and liquid crystal composition containing the same |
| JPWO2023127537A1 (en) * | 2021-12-28 | 2023-07-06 | ||
| WO2023127537A1 (en) * | 2021-12-28 | 2023-07-06 | 富士フイルム株式会社 | Multilayer body, optical element and light guide element |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4034835B2 (en) | 2008-01-16 |
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