JP2012067236A - Liquid crystal composition containing cyclohexane compound, and liquid crystal display device containing the composition - Google Patents
Liquid crystal composition containing cyclohexane compound, and liquid crystal display device containing the composition Download PDFInfo
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本発明は、新規なシクロヘキサン化合物を含有してなる液晶組成物に関するものであり、液晶ディスプレイの応答速度の改良を目的とするものである。 The present invention relates to a liquid crystal composition containing a novel cyclohexane compound, and aims to improve the response speed of a liquid crystal display.
液晶表示素子は液晶物質がもつ光学異方性(以下、Δnということがある。)および誘電率異方性(以下、Δεということがある。)を利用したものであり、時計を始め、電卓、測定機器、自動車用パネル、ワープロ、電子手帳、携帯電話、プリンター、コンピューター、TV等に利用されて来ている。この液晶表示素子に使用される液晶化合物には固有の液晶相が存在し、その相形態はネマチック相、スメクチック相及びコレステリック相に大別される。そのなかでも、ネマチック相が最も広く利用されている。また、表示装置に利用されている表示方式及び駆動方式のうち、表示方式としては、これまでに、動的散乱型(DSモード)、ゲスト・ホスト型(GHモード)、ねじれネマチック型(TNモード)、超ねじれネマチック型(STNモード)、薄膜トランジスター型(TFTモード)及び強誘電性液晶型(FLC)が開発されて来ている。最近はTN型、STN型およびTFT型の3種類が主流となっている。いずれの表示素子に用いられる液晶材料も、水分、空気、熱、光等に安定であることが必要であるうえ、室温を中心としてできるだけ広い温度範囲で液晶相を示し、適切な誘電率異方性(Δε)と屈折率異方性(Δn)有し、応答速度が速く、低電圧駆動ができる特性が必要となる。この特性を満たすためには、粘度が低く、低いしきい値電圧を有する液晶が必要とされる。現在のところ単一化合物では上記のような条件をすべて満たす物質はなく、数種から、数十種の液晶化合物を混合して要求特性に合致させているのが現状である。
さらに、近年の高精細TV,3D対応の表示等により、さらなる応答速度の改良が求められている。
The liquid crystal display element utilizes the optical anisotropy (hereinafter may be referred to as Δn) and the dielectric anisotropy (hereinafter may be referred to as Δε) of the liquid crystal substance. It has been used for measuring instruments, automotive panels, word processors, electronic notebooks, mobile phones, printers, computers, TVs, and the like. The liquid crystal compound used in this liquid crystal display element has a unique liquid crystal phase, and the phase form is roughly classified into a nematic phase, a smectic phase, and a cholesteric phase. Among them, the nematic phase is most widely used. Among display methods and drive methods used in display devices, display methods such as dynamic scattering type (DS mode), guest-host type (GH mode), and twisted nematic type (TN mode) have been used so far. ), Super twisted nematic type (STN mode), thin film transistor type (TFT mode) and ferroelectric liquid crystal type (FLC) have been developed. Recently, three types of TN type, STN type and TFT type have become mainstream. The liquid crystal material used for any display element must be stable to moisture, air, heat, light, etc., and exhibits a liquid crystal phase in the widest possible temperature range, centering on room temperature, with an appropriate anisotropic dielectric constant. Characteristics (Δε) and refractive index anisotropy (Δn), high response speed, and low voltage drive characteristics are required. In order to satisfy this characteristic, a liquid crystal having a low viscosity and a low threshold voltage is required. At present, no single compound satisfies all the above-mentioned conditions, and the present situation is that several to several tens of liquid crystal compounds are mixed to meet the required characteristics.
Furthermore, further improvement in response speed is required by recent high-definition TV, 3D compatible display, and the like.
さて、係る応答速度等の改良のため、現在汎用されているネマチック液晶組成物に添加して、粘度及びしきい値を低下させる化合物としては、特開平6−56716に記載されている式(a)で表わせる化合物群(特許文献1)、特開平7−126205に記載されている式(b)で表わせる化合物群(特許文献2)がある。
さらに、本発明者は、ネマチック液晶に混合させ応答速度を改良する化合物として、上記式(a)、(b)に示した化合物よりさらに効果がある式(1)で表わされる新規なシクロヘキサン化合物群について、特許出願した(特許文献3)。
さて、本発明は、上記の式(1)に示したシクロヘキサン化合物群を既知の各ネマチック液晶化合物に混合した場合の応答速度を研究し、より応答速度を改善するネマチック液晶組成物を提供するものである。 The present invention studies a response speed when the cyclohexane compound group represented by the above formula (1) is mixed with each known nematic liquid crystal compound, and provides a nematic liquid crystal composition that further improves the response speed. It is.
すなわち、第1発明は、第一成分として、式(1)で表わされるシクロヘキサン化合物群の少なくとも1種類の化合物を含有し、第二成分として式(2)、(3)、(4)及び(5)で表わされる各化合物群の少なくとも1種類の化合物を含有してなる液晶組成物である。
前述と重複するが、式(1)のシクロヘキサン化合物群は、本発明者が発明した新規化合物であり、先に特許出願(特願2010−162348)したものである。式(1)のシクロヘキサン化合物群は、液晶組成物の粘度を低下させ、応答速度を改善する機能を有している。
なお、式(1)及び式(2)から(5)の化合物群には上記のように多くの種類の化合物が含まれる。後述する式(6)も同様である。
第1発明の液晶組成物は、第一成分として、式(1)シクロヘキサン化合物群のうちの少なくとも1種類の化合物を含有することを条件とする液晶組成物である。
第二成分としては、式(2)、(3)、(4)及び(5)で表わされる各化合物群のうちの少なくとも1種類以上の化合物が組み合わされた液晶組成物である。すなわち、第二成分には、式(2)〜(5)の各化合物群の中の少なくとも1種類の化合物がそれぞれ含有されている。そして、この第一成分と第二成分が混合されて、第1発明の液晶組成物が構成され、応答速度が改善される。
Although it overlaps with the above-mentioned, the cyclohexane compound group of Formula (1) is a novel compound which this inventor invented, and patent application (Japanese Patent Application No. 2010-162348) previously. The cyclohexane compound group of the formula (1) has a function of reducing the viscosity of the liquid crystal composition and improving the response speed.
In addition, many types of compounds are contained in the compound group of Formula (1) and Formula (2) to (5) as described above. The same applies to equation (6) described later.
The liquid crystal composition of the first invention is a liquid crystal composition provided that it contains at least one compound of the formula (1) cyclohexane compound group as a first component.
The second component is a liquid crystal composition in which at least one compound of each compound group represented by formulas (2), (3), (4) and (5) is combined. That is, the second component contains at least one compound in each compound group of formulas (2) to (5). And this 1st component and 2nd component are mixed, the liquid-crystal composition of 1st invention is comprised, and a response speed is improved.
続いて、第2発明は、第1発明の第二成分中、式(2)の化合物群を除いた第1発明の液晶組成物である。 Subsequently, the second invention is the liquid crystal composition of the first invention excluding the compound group of the formula (2) in the second component of the first invention.
前述のように、式(1)のシクロヘキサン化合物群は、液晶組成物の粘度を低下させ、応答速度を改善する機能を有しているが、式(2)の化合物群も同様な機能を有している。そこで、式(2)の化合物群を含有しなくとも、式(1)の化合物群だけで、液晶組成物の応答速度を改善できる場合があり、式(2)の化合物群を除くものである。 As described above, the cyclohexane compound group of the formula (1) has a function of reducing the viscosity of the liquid crystal composition and improving the response speed, but the compound group of the formula (2) also has a similar function. is doing. Therefore, even if the compound group of the formula (2) is not contained, the response speed of the liquid crystal composition may be improved only by the compound group of the formula (1), and the compound group of the formula (2) is excluded. .
続いて、第3発明は、第1発明又は第2発明の液晶組成物に式(6)で表わされる化合物群の少なくとも1種類の化合物を、任意の割合で混合した液晶組成物である。
式(6)の化合物群も、液晶組成物の粘度を低下させ、応答速度を改善する機能を有しているため、これを混合した場合により応答速度が改善される場合があるからである。
Subsequently, the third invention is a liquid crystal composition in which at least one compound of the compound group represented by formula (6) is mixed in an arbitrary ratio with the liquid crystal composition of the first invention or the second invention.
This is because the compound group of the formula (6) also has a function of reducing the viscosity of the liquid crystal composition and improving the response speed, and therefore the response speed may be improved by mixing them.
第1発明では、式(1)で示した新規なシクロヘキサン化合物群を混合するネマチック液晶を限定し、より応答速度の速い液晶組成物を提供するものであり、第2発明では、さらにネマチック液晶組成物を限定するものである。第3発明では、第1発明あるいは第2発明の液晶組成物に特定の化合物群を混合し、さらなる応答速度の速い液晶組成物を提供するものである。 In the first invention, the nematic liquid crystal mixed with the novel cyclohexane compound group represented by the formula (1) is limited to provide a liquid crystal composition having a higher response speed. In the second invention, the nematic liquid crystal composition is further provided. The thing is limited. In the third invention, a specific compound group is mixed with the liquid crystal composition of the first invention or the second invention to provide a liquid crystal composition having a further faster response speed.
本発明の実施例を以下に示す Examples of the present invention are shown below.
式(3)から(5)のネマチック液晶を以下に示す割合で混合した。これは、式(2)の化合物群を除いた第2発明に基づく比較例であり、これを比較例1とする。
表1 比較例1
Nematic liquid crystals of the formulas (3) to (5) were mixed at the ratio shown below. This is a comparative example based on the second invention excluding the compound group of the formula (2).
Table 1 Comparative Example 1
表2は、表1の比較例1に式(2)の化合物群の1種類の化合物を混合したものであり、第1発明に基づく比較例であり、これを比較例2とする。
表2 比較例2
Table 2 is a comparative example based on the first invention, in which one type of compound of the compound group of formula (2) is mixed with Comparative Example 1 in Table 1, and this is referred to as Comparative Example 2.
Table 2 Comparative Example 2
表3に式(1)のシクロヘキサン化合物群の1種類を比較例1に混合したときの実施例1を示す。
表3 実施例1
Table 3 shows Example 1 when one type of the cyclohexane compound group of the formula (1) was mixed with Comparative Example 1.
Table 3 Example 1
表4に各比較例と実施例の応答速度測定結果を示す。
表4 応答速度測定結果
上記表4の応答速度は、印加電圧10V,オフセット電圧0.1V,周波数100Hzの印加時において、セルギャップ9μm、TNセルにて測定した結果である。
立ち上がり時間とは、誘電率が電圧オン時にゼロから最大誘電率の50%変化するまでの時間をいい、立ち下がり時間とは、誘電率が電圧オフ時に最大誘電率から50%変化するまでの時間をいう。表4ではいずれもmillisecond(msec)にて表わしている。
Table 4 shows the response speed measurement results of the comparative examples and the examples.
Table 4 Response speed measurement results
The response speeds in Table 4 are the results of measurement using a TN cell with a cell gap of 9 μm when an applied voltage of 10 V, an offset voltage of 0.1 V, and a frequency of 100 Hz are applied.
The rise time refers to the time until the dielectric constant changes from zero to 50% of the maximum dielectric constant when the voltage is on, and the fall time refers to the time until the dielectric constant changes by 50% from the maximum dielectric constant when the voltage is off. Say. In Table 4, all are expressed in millisecond (msec).
近年の高精細TV,3D対応の表示等により、さらなる応答速度の改良が求められている状況下において、係るネマチック液晶組成物の需要が期待できる。 Demand for such a nematic liquid crystal composition can be expected in a situation where further improvement in response speed is required due to recent high-definition TV, 3D compatible display, and the like.
すなわち、第1発明は、第一成分として、式(1)で表わされるシクロヘキサン化合物群の少なくとも1種類の化合物を含有し、第二成分として式(2)、(3)、(4)及び(5)で表わされる各化合物群の少なくとも1種類の化合物を含有してなる液晶組成物である。
該アルキル基は不飽和結合を有していてもよく、該基中−CH2−は,−O−,−CO−,又は−COOで置換されていても良く、また、一部あるいは全ての水素原子がハロゲン原子又はシアノ基により置換されていてもよい。X,Yは各々独立にハロゲン原子又は水素原子を表わし、同時に水素原子を表わすことはない。また、あるいは、Xは酸素原子を表わしYは該酸素原子への直接結合を表わす。)
(Rは、アルキル基、Xは、H又はFを表す。)
That is, the first invention contains at least one compound of the cyclohexane compound group represented by formula (1) as the first component, and formulas (2), (3), (4) and ( 5) A liquid crystal composition comprising at least one compound of each compound group represented by 5).
The alkyl group may have an unsaturated bond, and —CH 2 — in the group may be substituted with —O—, —CO—, or —COO, and some or all of them may be substituted. The hydrogen atom may be substituted with a halogen atom or a cyano group. X and Y each independently represent a halogen atom or a hydrogen atom, and do not represent a hydrogen atom at the same time. Alternatively, X represents an oxygen atom, and Y represents a direct bond to the oxygen atom. )
(R represents an alkyl group, and X represents H or F.)
続いて、第2発明は、第1発明の第二成分中、式(2)の化合物群を含有せず、式(3)、(4)及び(5)で表わされる各化合物群の少なくとも1種類の化合物群を含有してなる、第1発明の液晶組成物である。 Then, 2nd invention does not contain the compound group of Formula (2) in the 2nd component of 1st invention , At least 1 of each compound group represented by Formula (3), (4) and (5) 1 is a liquid crystal composition according to a first aspect of the present invention , which comprises a group of compounds .
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JP2010214647A JP4669085B1 (en) | 2010-09-27 | 2010-09-27 | Liquid crystal composition and liquid crystal display element containing cyclohexane compound |
PCT/JP2011/065112 WO2012011375A1 (en) | 2010-07-17 | 2011-06-30 | Cyclohexane compound and liquid crystal composition containing said compound |
KR1020127020365A KR101431935B1 (en) | 2010-07-17 | 2011-06-30 | Cyclohexane compound and liquid crystal composition containing said compound |
CN201180007471.XA CN102822129B (en) | 2010-07-17 | 2011-06-30 | Cyclohexane compound and liquid crystal composition containing said compound |
EP11809549.6A EP2594548B1 (en) | 2010-07-17 | 2011-06-30 | Cyclohexane compound and liquid crystal composition containing said compound |
US13/634,942 US8858829B2 (en) | 2010-07-17 | 2011-06-30 | Cyclohexane compound and liquid crystal composition containing the same |
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US9284488B2 (en) | 2013-09-05 | 2016-03-15 | Samsung Display Co., Ltd. | Liquid crystal display device |
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TWI500747B (en) * | 2012-10-04 | 2015-09-21 | Chiracol Co Ltd | A liquid crystal composition containing a cyclohexane compound, and a liquid crystal display element |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0931461A (en) * | 1995-07-21 | 1997-02-04 | Chisso Corp | Liquid crystal composition and liquid crystal display element |
JPH1046150A (en) * | 1996-08-06 | 1998-02-17 | Dainippon Ink & Chem Inc | Nematic liquid crystal composition and liquid crystal display using the same |
JPH10140157A (en) * | 1996-10-31 | 1998-05-26 | Merck Patent Gmbh | Tn and stn liquid crystal displays |
JPH10245559A (en) * | 1997-02-27 | 1998-09-14 | Merck Patent Gmbh | Electrooptical liquid crystal display |
JPH1112199A (en) * | 1997-06-04 | 1999-01-19 | Merck Patent Gmbh | Cyclohexane derivative and liquid crystal medium |
US6475595B1 (en) * | 1999-03-31 | 2002-11-05 | Merck Gmbh | Fluorocyclohexene derivatives, and liquid-crystalline medium |
JP2007091796A (en) * | 2005-09-27 | 2007-04-12 | Dainippon Ink & Chem Inc | Nematic liquid crystal composition |
-
2010
- 2010-09-27 JP JP2010214647A patent/JP4669085B1/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0931461A (en) * | 1995-07-21 | 1997-02-04 | Chisso Corp | Liquid crystal composition and liquid crystal display element |
JPH1046150A (en) * | 1996-08-06 | 1998-02-17 | Dainippon Ink & Chem Inc | Nematic liquid crystal composition and liquid crystal display using the same |
JPH10140157A (en) * | 1996-10-31 | 1998-05-26 | Merck Patent Gmbh | Tn and stn liquid crystal displays |
JPH10245559A (en) * | 1997-02-27 | 1998-09-14 | Merck Patent Gmbh | Electrooptical liquid crystal display |
JPH1112199A (en) * | 1997-06-04 | 1999-01-19 | Merck Patent Gmbh | Cyclohexane derivative and liquid crystal medium |
US6475595B1 (en) * | 1999-03-31 | 2002-11-05 | Merck Gmbh | Fluorocyclohexene derivatives, and liquid-crystalline medium |
JP2007091796A (en) * | 2005-09-27 | 2007-04-12 | Dainippon Ink & Chem Inc | Nematic liquid crystal composition |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9284488B2 (en) | 2013-09-05 | 2016-03-15 | Samsung Display Co., Ltd. | Liquid crystal display device |
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