JP2005015688A - Nematic liquid crystal composition containing indane compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a nematic liquid crystal composition having a lower low limit temperature (T<SB>→N</SB>) of the liquid crystal phase, a high upper limit temperature (T<SB>N-I</SB>) of the liquid crystal phase and low viscosity by using an indane compound. <P>SOLUTION: The indane compound is expressed by formula (I). This nematic liquid crystal composition is produced by using a specific liquid crystal compound. The nematic liquid crystal composition has a wide liquid crystal phase temperature range and, accordingly, is extremely useful as an active matrix liquid crystal display element having a wide service temperature range and usable outdoors and in a car. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

（式中Ｒは炭素原子数５〜７のアルキル基であり、Ｘ^６、Ｘ^８はそれぞれ独立してＨ、Ｃｌ又はＦであり、Ｘ^７はＣｌ又はＦである。）で表される化合物が良く用いられているが、液晶相上限温度（Ｔ_Ｎ−Ｉ） の低下を防ぐ目的で式中のＲは炭素原子数５〜７のアルキル基であることが多い（特許文献２参照）。しかしながらこれらの材料では液晶相の下限温度（Ｔ_{→ Ｎ}）を十分に下げることができないことと、粘性の上昇を引き起こす問題があった。
【０００５】
一方、骨格中にインダンを有する液晶化合物は既に知られており、幾つかの化合物が開示されている（特許文献３参照）。しかしながら、インダン環の５位及び６位にフッ素原子を有する化合物の開示はあるものの、当該化合物をネマチック液晶組成物として使用した場合どのような特徴を有するかは開示されていない。又、インダン系化合物を用いた液晶組成物も既に知られており、好ましい化合物の具体例が開示されている（特許文献４参照）。しかしながら、ここで開示されている化合物はインダン環の５位及び６位にフッ素原子を有するものではなく、２位の置換基も主として特殊な環構造か非環構造を有するものである。しかも、ここで開示される液晶組成物は強誘電性液晶表示素子に使用する液晶組成物であり、ネマチック液晶組成物に関する開示はない。
【０００６】
以上より、インダン環の５位及び６位にフッ素原子等を有する化合物を応用したネマチック液晶組成物は知られておらず、インダン系化合物を用いた、液晶相温度範囲が広く、低い粘性を有するネマチック液晶組成物の開発が望まれていた。
【０００７】
【特許文献１】
特開２００１−１１４５０号公報（６頁）
【特許文献２】
特表平４−５０１５７５号公報（２３頁）
【特許文献３】
国際公開第９４／１８２８５号パンフレット（２６〜３１頁）
【特許文献４】
国際公開第９９／１９４２０号パンフレット（３０〜３５頁）
【０００８】
【発明が解決しようとする課題】
本発明の課題は、インダン系化合物を用いた、液晶相の下限温度（Ｔ_{→ Ｎ}）が低く、液晶相上限温度（Ｔ_Ｎ−Ｉ）が高く、さらに粘性の低いネマチック液晶組成物を提供することである。
【０００９】
【課題を解決するための手段】
本発明者は、上記課題を解決するために、インダン化合物を含有するネマチック液晶組成物を検討した結果本件発明を完成するに至った。
【００１０】
すなわち、本発明は以下に記載のネマチック液晶組成物を提供する。
【００１１】
一般式（Ｉ）
【化７】

（式中Ｒ^１は、水素原子、炭素数１〜１５のアルキル基、少なくとも一つのハロゲンにより置換された炭素数１〜１５のアルキル基、炭素数２〜１５のアルケニル基又は少なくとも一つのハロゲンにより置換された炭素数２〜１５のアルケニル基を表し、これらの基中に存在する１個又は２個以上のＣＨ_２基はそれぞれ独立してＯ原子が相互に直接結合しないものとして −Ｏ−、−Ｓ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−又は−ＯＣＯ−Ｏ−により置き換えられても良く、
Ａ^１は、
（ａ） トランス−１，４−シクロへキシレン基（この基中に存在する１個のＣＨ_２基又は隣接していない２個以上のＣＨ_２基は −Ｏ− 及び又は −Ｓ− に置き換えられてもよい）
（ｂ） １，４−フェニレン基（この基中に存在する１個のＣＨ_２基又は隣接していない２個以上のＣＨ_２基は −Ｎ− に置き換えられてもよい）
からなる群より選ばれる基であり、上記の基（ａ）、基（ｂ）はＣＮ又はハロゲンで置換されていても良く、
ｎは、０又は１であり、
Ｚ^１は、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−（ＣＨ_２）_４−、−ＣＨ＝ＣＨ−ＣＨ_２ＣＨ_２−、−ＣＨ_２ＣＨ_２−ＣＨ＝ＣＨ− 又は単結合であり、
Ｚ^２は、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ− 又は単結合であり、
Ｘ^１、Ｘ^２はそれぞれ独立して、−Ｈ、−Ｆ、−Ｃｌ、−ＣＦ_３、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３、−ＣＨ_２ＣＦ_３である。）から選ばれる化合物を１種又は２種以上を含有し、一般式（ＩＩ）
【００１２】
【化８】

（式中、Ｒ^２及びＲ^３はそれぞれ独立的にＲ^１と同じ意味を表し、
Ｂ^１、Ｂ^２及びＢ^３はそれぞれ独立的に
（ａ） トランス−１，４−シクロへキシレン基（この基中に存在する１個のＣＨ_２基又は隣接していない２個以上のＣＨ_２基は −Ｏ− 及び又は −Ｓ− に置き換えられてもよい）
（ｂ） １，４−フェニレン基（この基中に存在する１個のＣＨ_２基又は隣接していない２個以上のＣＨ_２基は −Ｎ− に置き換えられてもよい）
からなる群より選ばれる基であり、上記の基（ａ）、基（ｂ）はＣＮ又はハロゲンで置換されていても良く、
ｏは０、１又は２であり、
Ｌ^１及びＬ^２はそれぞれ独立的に単結合、−ＣＨ_２ＣＨ_２−、−（ＣＨ_２）_４−、−ＯＣＨ_２−、−ＣＨ_２Ｏ−、−ＯＣＦ_２−、−ＣＦ_２Ｏ−又は−Ｃ≡Ｃ−を表し、Ｌ^２及びＢ^３が複数存在する場合はそれらは同一でも良く異なっていても良い。）から選ばれる化合物及び一般式（ＩＩＩ）
【００１３】
【化９】

【００１４】
（式中Ｒ^４はＲ^１と同じ意味を表し、Ｃ^１及びＣ^２はそれぞれ独立して、
（ａ） トランス−１，４−シクロへキシレン基（この基中に存在する１個のＣＨ_２基又は隣接していない２個以上のＣＨ_２基は −Ｏ− 及び又は −Ｓ− に置き換えられてもよい）
（ｂ） １，４−フェニレン基（この基中に存在する１個のＣＨ_２基又は隣接していない２個以上のＣＨ_２基は −Ｎ− に置き換えられてもよい）
からなる群より選ばれる基であり、上記の基（ａ）、基（ｂ）はＣＮ又はハロゲンで置換されていても良く、
Ｋ^１及びＫ^２はそれぞれ独立的に単結合、−ＣＨ_２ＣＨ_２−、−（ＣＨ_２）_４−、−ＯＣＨ_２−、−ＣＨ_２Ｏ−、−ＯＣＦ_２−、−ＣＦ_２Ｏ−又は−Ｃ≡Ｃ−を表し、
Ｘ^３及びＸ^５はそれぞれ独立してＨ又はＦであり、
ｐは１又は２であり、
Ｘ^４は、−Ｈ、−Ｆ、−Ｃｌ、−ＣＮ、−ＣＦ_３、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３、−ＣＨ_２ＣＦ_３又はＲ^１と同じ定義である。）から選ばれる１種又は２種以上の化合物を含有することを特徴とするネマチック液晶組成物を提供する。
【００１５】
【発明の実施の形態】
以下に本発明の一例について説明する。
【００１６】
本発明において、第一成分として一般式（Ｉ）から選ばれる化合物を１種又は２種以上を含有するが、１種〜６種が好ましく、１種〜４種がより好ましく、１種〜３種が特に好ましい。
【００１７】
一般式（Ｉ）の含有率が５〜５０質量％の範囲であることが好ましく、１０〜４０質量％の範囲であることが特に好ましい。また、Ｒ^１は、炭素数１〜１０のアルキル基又は炭素数２〜１０のアルケニル基が好ましく、未置換の直鎖状炭素数１〜８のアルキル基又は炭素数２〜８のアルケニル基がより好ましく、アルケニル基では以下の式（ａ）〜（ｅ）の構造がさらに好ましい。
【化１０】

（構造式は右端で環に連結しているものとする。）
【００１８】
Ａ^１はトランス−１，４−シクロへキシレン基、１，３−ジオキサン−トランス−２，５−ジイル基、１，４−フェニレン基、３−フルオロ−１，４−フェニレン基又は３，５−ジフルオロ−１，４−フェニレン基が好ましく、１，３−ジオキサン−トランス−２，５−ジイル基、１，４−フェニレン基又はトランス−１，４−シクロへキシレン基がより好ましい。Ｚ^１は、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−（ＣＨ_２）_４−、−ＣＨ＝ＣＨ−ＣＨ_２ＣＨ_２−、−ＣＨ_２ＣＨ_２−ＣＨ＝ＣＨ− 又は単結合であるが、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２ＣＨ_２−、−Ｃ≡Ｃ−、−（ＣＨ_２）_４−又は単結合が好ましく、−ＣＨ_２ＣＨ_２−、−Ｃ≡Ｃ−又は単結合がより好ましく、−ＣＨ_２ＣＨ_２−又は単結合が特に好ましい。Ｚ^２は、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ−、又は単結合であるが、−ＣＨ_２ＣＨ_２−、又は単結合が好ましく、単結合がより好ましい。ｎは０又は１であるが、０であることが好ましい。Ｘ^１、Ｘ^２はそれぞれ独立して、−Ｈ、−Ｆ、−Ｃｌ、−ＣＦ_３、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３、−ＣＨ_２ＣＦ_３であるが、−Ｆ、−Ｃｌ、−ＣＦ_３、−ＯＣＨＦ_２、−ＯＣＦ_３が好ましく、−Ｆ、−ＣＦ_３、−ＯＣＦ_３がより好ましく、Ｆが特に好ましい。
【００１９】
具体的な構造として以下の一般式（Ｉａ）
【化１１】

（式中Ｒ^１、Ａ^１、Ｚ^１、及びｎは一般式（Ｉ）におけると同じ意味を表す。）が好ましく、次の化合物が特に好ましく、
【００２０】
【化１２】

（式中、Ｒ^１は、炭素原子数１〜８のアルキル基又はアルコキシル基を表す。）次の化合物もまた好ましい。
【００２１】
【化１３】

（式中、Ｒ^１は、炭素原子数１〜８のアルキル基又はアルコキシル基を表す。）
これらの一般式（Ｉ）から選ばれる化合物のうち少なくとも１種以上の組成物の誘電率異方性（Δε）が１．５以上の化合物を含有することが好ましく、２以上を示すことがより好ましい。
【００２２】
第二成分として一般式（ＩＩ）の化合物を１種又は２種以上を含有するが、１種〜２０種が好ましく、１種〜１５種がより好ましく、１種〜１０種が特に好ましく、さらに１種〜５種が特に好ましい。また、これらの含有率は５質量％〜５０質量％が好ましく、５質量％〜３０質量％がより好ましい。
【００２３】
一般式（ＩＩ）においてＲ^２及びＲ^３は、未置換の直鎖状炭素数１〜１５のアルキル基又は炭素数２〜１５のアルケニル基、−ＣＦ_３、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３が好ましく、未置換の直鎖状炭素数１〜１０のアルキル基又は炭素数２〜１０のアルケニル基、−ＣＦ_３、−ＯＣＨＦ_２、−ＯＣＦ_３がより好ましく、未置換の直鎖状炭素数１〜８のアルキル基又は炭素数２〜６のアルケニル基、−ＣＦ_３、−ＯＣＦ_３が特に好ましく、アルケニル基では式（ａ）〜（ｅ）の構造がさらに好ましい。
また、Ｒ^２及びＲ^３は同一でも異なっていても良いが、同一分子中のＲ^２及びＲ^３は異なっていることがより好ましい。Ｌ^１及びＬ^２は、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２ＣＨ_２−、−Ｃ≡Ｃ−、−（ＣＨ_２）_４−又は単結合が好ましく、−ＣＨ_２ＣＨ_２−、−Ｃ≡Ｃ−又は単結合がより好ましく、−ＣＨ_２ＣＨ_２−又は単結合が特に好ましく、Ｌ^１及びＬ^２が複数存在する場合少なくとも一つは単結合であることが好ましい。ｏは、０又は１が好ましい。
【００２４】
Ｂ^１、Ｂ^２及びＢ^３はそれぞれ独立してトランス−１，４−シクロへキシレン基、１，４−フェニレン基、３−フルオロ−１，４−フェニレン基又は３，５−ジフルオロ−１，４−フェニレン基が好ましく、トランス−１，４−シクロへキシレン基又は１，４−フェニレン基より好ましく、Ｂ^１、Ｂ^２及びＢ^３の内少なくとも一つはトランス−１，４−シクロへキシレン基であることが好ましい。
【００２５】
一般式（ＩＩ）は具体的な構造として以下の一般式（ＩＩａ）で示される構造が好ましい。
【化１４】

（式中、Ｒ^２及びＲ^３は炭素原子数１〜８のアルキル基又はアルコキシル基、炭素原子数２〜８のアルケニル基、炭素原子数３〜１６のアルケニルオキシ基、−ＣＦ_３、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３を表し、Ｂ^３は１，４−フェニレン基又はトランス−１，４−シクロヘキシレン基を表し、ｒは０又は１を表す。）
一般式（ＩＩａ）の化合物の含有率は５〜５０質量％の範囲であることが好ましい。
【００２６】
又、以下の一般式で示される構造も好ましい。
【化１５】

（式中、Ｒ^５、Ｒ^６は炭素原子数１〜８のアルキル基又はアルコキシル基、炭素原子数２〜８のアルケニル基、炭素原子数３〜１６のアルケニルオキシ基、−ＣＦ_３、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３を表す。）で示される構造が好ましい。
【００２７】
第三成分として一般式（ＩＩＩ）の化合物を１種又は２種以上を含有するが、１種〜２０種が好ましく、１種〜１５種がより好ましく、１種〜１０種が特に好ましく、さらに５種〜１０種が特に好ましい。また、これらの含有率は１０質量％〜８５質量％が好ましい。
【００２８】
一般式（ＩＩＩ）においてＲ^４は、未置換の直鎖状炭素数１〜１５のアルキル基又は炭素数２〜１５のアルケニル基が好ましく、未置換の直鎖状炭素数１〜１０のアルキル基又は炭素数２〜１０のアルケニル基がより好ましく、未置換の直鎖状炭素数１〜８のアルキル基又は炭素数２〜６のアルケニル基が特に好ましく、アルケニル基では式（ａ）〜（ｅ）の構造がさらに好ましい。Ｋ^１及びＫ^２は、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２ＣＨ_２−、−Ｃ≡Ｃ−、−ＯＣＦ_２−、−ＣＦ_２Ｏ−、−（ＣＨ_２）_４−又は単結合が好ましく、−ＣＨ_２ＣＨ_２−、−Ｃ≡Ｃ−、−ＯＣＦ_２−、−ＣＦ_２Ｏ−又は単結合がより好ましく、−ＣＨ_２ＣＨ_２−又は単結合が特に好ましく、Ｋ^１又はＫ^２が複数存在する場合少なくとも一つは単結合であることが好ましい。ｐは１が好ましい。Ｃ^１及びＣ^２はそれぞれ独立してトランス−１，４−シクロへキシレン基、１，４−フェニレン基、３−フルオロ−１，４−フェニレン基又は３，５−ジフルオロ−１，４−フェニレン基が好ましく、トランス−１，４−シクロへキシレン基又は１，４−フェニレン基より好ましく、トランス−１，４−シクロへキシレン基が特に好ましい。
【００２９】
Ｘ^４は、−Ｈ、−Ｆ、−Ｃｌ、−ＣＮ、−ＣＦ_３、−ＣＨＦ_２、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３、−ＣＨ_２ＣＦ_３又はＲ^１と同じ定義であるが、−Ｆ、−ＣＮ、−ＣＦ_３、−ＣＨＦ_２、−ＯＣＨ_２Ｆ、−ＯＣＨＦ_２、−ＯＣＦ_３が好ましく、Ｆが特に好ましい。
【００３０】
一般式（ＩＩＩ）は具体的な構造として、一般式（ＩＩＩ−１）
【化１６】

（式中、Ｒ^７は炭素原子数１〜８のアルキル基又はアルコキシル基、炭素原子数２〜８のアルケニル基を表し、Ｌ^５、Ｌ^６はそれぞれ独立して、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−（ＣＨ_２）_４−、−ＯＣＦ_２−、−ＣＦ_２Ｏ−又は単結合を表し、環Ｉは１，４−フェニレン基又はトランス−１，４−シクロヘキシレン基を表し、Ｘ^９はＨ又はＦを表し、Ｙ^４は−ＣＮ、−Ｆ、−Ｃｌ、−ＣＦ_３、−ＯＣＦ_３又は−ＯＣＨＦ_２を表す。）で示される構造が好ましい。
【００３１】
また、一般式（ＩＩＩ）は具体的な構造として以下の一般式
【化１７】

【００３２】
【化１８】

（式中、Ｒ^７は炭素原子数１〜８のアルキル基又はアルコキシル基、炭素原子数２〜８のアルケニル基を表し、Ｘ^３及びＸ^４はそれぞれ独立してＨ又はＦを表し、Ｙ^４は−ＣＮ、−Ｆ、−Ｃｌ、−ＣＦ_３、−ＯＣＦ_３又は−ＯＣＨＦ_２を表す。）で示される構造も好ましい。
【００３３】
本発明のネマチック液晶組成物は一般式（Ｉａ）の化合物を１種又は２種以上含有し、さらに一般式（ＩＩ）の化合物を１種又は２種以上含有し、さらに一般式（ＩＩＩ）の化合物を１種又は２種以上含有することが好ましい。
【００３４】
又、一般式（Ｉａ）で表される化合物を１種又は２種以上を含有し、その含有率が５〜５０質量％の範囲で、なおかつ一般式（ＩＩａ）の化合物を１種又は２種以上を含有し、その含有率が１０〜５０質量％の範囲で、なおかつ一般式（ＩＩＩ）の化合物を１種又は２種以上を含有し、その含有率が５〜８０質量％の範囲であることが好ましい。
【００３５】
さらに、一般式（Ｉａ）で表される化合物を１種〜３種含有し、その含有率が１０〜４０質量％の範囲であり、一般式（ＩＩ）で表される化合物を１種〜５種含有し、その含有率が５質量％〜３０質量％の範囲であり、一般式（ＩＩＩ）で表される化合物を５種〜１０種含有し、その含有率が１０質量％〜８５質量％の範囲であることが特に好ましい。
【００３６】
本発明のネマチック液晶組成物は広い液晶相温度範囲（液晶相下限温度と液晶相上限温度の差の絶対値）を有するが、液晶相温度範囲が８０℃以上であることが好ましく、９０℃以上であることがより好ましく、１００℃以上が特に好ましい。また、液晶相上限温度は７０℃以上が好ましく、８０℃以上がより好ましい。さらに、液晶相下限温度は−２０℃以下が好ましく、−３０℃以下がより好ましい。
【００３７】
上記ネマチック液晶組成物はＡＭ−ＬＣＤやＳＴＮ−ＬＣＤに有用であるがＡＭ−ＬＣＤに特に有用であり、透過型あるいは反射型の液晶表示素子に用いることができる。本発明のネマチック液晶組成物は、上記の化合物以外に、通常のネマチック液晶、スメクチック液晶、コレステリック液晶などを含有していてもよい。
【００３８】
【実施例】
以下、実施例を挙げて本発明を更に詳述するが、本発明はこれらの実施例に限定されるものではない。また、以下の実施例及び比較例の組成物における「％」は『質量％』を意味する。
【００３９】
実施例中、測定した特性は以下の通りである。

【００４０】
【化１９】

【００４１】
（実施例１、比較例１及び２） 液晶組成物の調整
以下に示すネマチック液晶組成物（Ｎｏ．１）、（Ｒ１）及び（Ｒ２）を調整しその物性値を測定し、その結果を表１に示す。
【表１】

【００４２】
表１に示すように、実施例１のネマチック液晶組成物は比較例１のネマチック液晶組成物と比較して、液晶相の下限温度（Ｔ_{→ Ｎ}）が高く、液晶相上限温度（Ｔ_Ｎ−Ｉ）が低く、広い液晶温度範囲を有することが解る。
このネマチック液晶組成物を用いて、ＴＦＴ液晶表示素子を作製しその応答速度を測定したところ、実施例１のネマチック液晶組成物を使用したＴＦＴ液晶素子では４３ｍｓで応答することができたが、比較例１のネマチック液晶組成物を使用したＴＦＴ液晶素子では応答時間が４７ｍｓであり、実施例１の方が優れていた。
【００４３】
同様に、実施例１のネマチック液晶組成物は比較例２のネマチック液晶組成物と比較して、液晶相の下限温度（Ｔ_{→ Ｎ}）が高く、液晶相上限温度（Ｔ_Ｎ−Ｉ）が低く、広い液晶温度範囲を有することが解る。
また比較例２のネマチック液晶組成物を使用したＴＦＴ液晶素子の応答時間は４５ｍｓであり、実施例１の方が優れていた。
【００４４】
（実施例２及び３） 液晶組成物の調整
以下に示すネマチック液晶組成物（Ｎｏ．２）及び（Ｎｏ．３）を調整しその物性値を測定し、その結果を表１に示す。
【表２】

【００４５】
表３に示すように、実施例２及び３のネマチック液晶組成物は、液晶相の下限温度（Ｔ_{→ Ｎ}）が高く、液晶相上限温度（Ｔ_Ｎ−Ｉ）が低く、広い液晶温度範囲を有することが解る。
このネマチック液晶組成物を用いて、表示品位の優れたＴＦＴ液晶表示素子を作成することができた。
【００４６】
【発明の効果】
本発明のネマチック液晶組成物により、インダン系化合物を用いた、液晶相の下限温度が低く、液晶相上限温度が高く、粘性の低いネマチック液晶組成物を提供することが可能となった。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a nematic crystal composition useful as an electro-optical liquid crystal display material, a liquid crystal display element using the composition, and an indane compound useful as a constituent material of the nematic liquid crystal composition.
[0002]
[Prior art]
In liquid crystal display elements such as twisted nematic, super twisted nematic or active matrix, especially in small and medium portable liquid crystal display elements, the stability of display with respect to the operating environment temperature is an important point. Liquid crystal material with lower driving voltage that can reduce power consumption, driving voltage in the temperature range of -30 to 0 ° C. or 40 to 80 ° C., steepness, desired duty driving frequency dependency, etc. It has been demanded.
[0003]
In particular, the liquid crystal phase temperature range (ΔT), which is the absolute value of the difference between the liquid crystal phase lower limit temperature (T _{→ N} ) and the liquid crystal phase upper limit temperature (T _N-I ), takes advantage of the low power consumption characteristics of the liquid crystal display element. This is important due to increased outdoor use. However, with the combination of conventional materials, although the liquid crystal phase temperature range can be expanded, the threshold voltage increases and the response speed increases accordingly, so that a sufficient liquid crystal phase temperature range is not obtained. (See Patent Document 1). Therefore, development of a liquid crystal composition having a wide liquid crystal phase temperature range without deteriorating liquid crystal characteristics such as response speed and threshold voltage, or development of a liquid crystal material optimal for this application has been desired.
[0004]
In order to adjust the liquid crystal phase upper limit temperature (T _N-I ) and expand the liquid crystal phase temperature range, the following general formula (IV)
[Chemical 6]

(Wherein R is an alkyl group having 5 to 7 carbon atoms, X ⁶ and X ⁸ are each independently H, Cl or F, and X ⁷ is Cl or F). Is often used, but R in the formula is often an alkyl group having 5 to 7 carbon atoms for the purpose of preventing the liquid crystal phase upper limit temperature (T _N-I ) from decreasing (see Patent Document 2). However, these materials have a problem that the lower limit temperature (T _{→ N} ) of the liquid crystal phase cannot be sufficiently lowered and the viscosity is increased.
[0005]
On the other hand, liquid crystal compounds having indane in the skeleton are already known, and some compounds have been disclosed (see Patent Document 3). However, although there is disclosure of a compound having fluorine atoms at the 5th and 6th positions of the indane ring, it is not disclosed what characteristics the compound has when used as a nematic liquid crystal composition. In addition, liquid crystal compositions using indane compounds are already known, and specific examples of preferred compounds are disclosed (see Patent Document 4). However, the compounds disclosed here do not have fluorine atoms at the 5th and 6th positions of the indane ring, and the substituent at the 2nd position mainly has a special ring structure or a non-ring structure. Moreover, the liquid crystal composition disclosed herein is a liquid crystal composition used for a ferroelectric liquid crystal display device, and there is no disclosure regarding a nematic liquid crystal composition.
[0006]
From the above, a nematic liquid crystal composition using a compound having a fluorine atom or the like at the 5-position and 6-position of the indane ring is not known, and the liquid crystal phase temperature range using the indane-based compound is wide and has low viscosity. Development of nematic liquid crystal compositions has been desired.
[0007]
[Patent Document 1]
JP 2001-11450 A (page 6)
[Patent Document 2]
JP 4-501575 A (page 23)
[Patent Document 3]
International Publication No. 94/18285 (26-31 pages)
[Patent Document 4]
WO99 / 19420 pamphlet (pages 30-35)
[0008]
[Problems to be solved by the invention]
An object of the present invention is to provide a nematic liquid crystal composition that uses an indane compound and has a low liquid crystal phase lower limit temperature (T _{→ N} ), a higher liquid crystal phase upper limit temperature (T _N-I ), and a lower viscosity. That is.
[0009]
[Means for Solving the Problems]
As a result of studying a nematic liquid crystal composition containing an indane compound in order to solve the above problems, the present inventor has completed the present invention.
[0010]
That is, the present invention provides the nematic liquid crystal composition described below.
[0011]
Formula (I)
[Chemical 7]

Wherein R ¹ is a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 15 carbon atoms substituted with at least one halogen, an alkenyl group having 2 to 15 carbon atoms or at least one halogen. Represents a substituted alkenyl group having 2 to 15 carbon atoms, and one or two or more CH ₂ groups present in these groups are each independently —O—, wherein O atoms are not directly bonded to each other, May be replaced by -S-, -CO-, -COO-, -OCO- or -OCO-O-;
A ¹ is,
(A) trans-1,4-one CH ₂ group or nonadjacent two or more CH ₂ groups existing in xylene group (in this group the cycloalkyl is replaced by -O- and or -S- May be)
(B) 1,4-phenylene group (one CH ₂ group present in this group or two or more non-adjacent CH ₂ groups may be replaced by —N—)
A group selected from the group consisting of the above-mentioned groups (a) and (b) may be substituted with CN or halogen;
n is 0 or 1;
Z ¹ is —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, — (CH ₂ ) ₄ —, _{-CH = CH-CH 2 CH 2} -, - a CH 2 CH 2 -CH = CH- or a single bond,
Z ² is —CH ₂ CH ₂ —, —CH═CH— or a single bond,
X ¹ and X ² are each independently —H, —F, —Cl, —CF ₃ , —OCH ₂ F, —OCHF ₂ , —OCF ₃ , —CH ₂ CF ₃ . ) Containing one or more compounds selected from general formula (II)
[0012]
[Chemical 8]

(Wherein R ² and R ³ each independently represent the same meaning as R ¹ ,
B ¹ , B ² and B ³ are each independently (a) a trans-1,4-cyclohexylene group (one CH ₂ group present in this group or two or more CH ₂ not adjacent to each other). Group may be replaced by -O- and / or -S-)
(B) 1,4-phenylene group (one CH ₂ group present in this group or two or more non-adjacent CH ₂ groups may be replaced by —N—)
A group selected from the group consisting of the above-mentioned groups (a) and (b) may be substituted with CN or halogen;
o is 0, 1 or 2;
L ¹ and L ² are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O— or -C≡C-, and when there are a plurality of L ² and B ^3, they may be the same or different. And a compound selected from general formula (III)
[0013]
[Chemical 9]

[0014]
(Wherein R ⁴ represents the same meaning as R ^1, and C ¹ and C ² are each independently
(A) trans-1,4-one CH ₂ group or nonadjacent two or more CH ₂ groups existing in xylene group (in this group the cycloalkyl is replaced by -O- and or -S- May be)
(B) 1,4-phenylene group (one CH ₂ group present in this group or two or more non-adjacent CH ₂ groups may be replaced by —N—)
A group selected from the group consisting of the above-mentioned groups (a) and (b) may be substituted with CN or halogen;
K ¹ and K ² are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O— or -C≡C-
X ³ and X ⁵ are each independently H or F;
p is 1 or 2,
X ⁴ has the same definition as —H, —F, —Cl, —CN, —CF ₃ , —OCH ₂ F, —OCHF ₂ , —OCF ₃ , —CH ₂ CF ₃ or R ¹ . And a nematic liquid crystal composition comprising one or more compounds selected from the group consisting of:
[0015]
DETAILED DESCRIPTION OF THE INVENTION
An example of the present invention will be described below.
[0016]
In this invention, the compound chosen from general formula (I) as a 1st component contains 1 type (s) or 2 or more types, However, 1 type-6 types are preferable, 1 type-4 types are more preferable, 1 type-3 Species are particularly preferred.
[0017]
The content of the general formula (I) is preferably in the range of 5 to 50% by mass, and particularly preferably in the range of 10 to 40% by mass. R ¹ is preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and an unsubstituted linear alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms. More preferably, in the case of an alkenyl group, structures of the following formulas (a) to (e) are more preferable.
Embedded image

(The structural formula shall be connected to the ring at the right end.)
[0018]
A ¹ is trans-1,4-cyclohexylene group, 1,3-dioxane-trans-2,5-diyl group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group, or 3,5. A -difluoro-1,4-phenylene group is preferred, and a 1,3-dioxane-trans-2,5-diyl group, a 1,4-phenylene group or a trans-1,4-cyclohexylene group is more preferred. Z ¹ is —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, — (CH ₂ ) ₄ —, —CH═CH—CH ₂ CH ₂ —, —CH ₂ CH ₂ —CH═CH— or a single bond, but —COO—, —OCO—, —CH ₂ CH ₂ —, —C≡C—, — (CH ₂ ) ₄ — or a single bond is preferred, —CH ₂ CH ₂ —, —C≡C— or a single bond is more preferred, —CH ₂ CH ₂ — or a single bond is particularly preferred. Z ² is —CH ₂ CH ₂ —, —CH═CH—, or a single bond, preferably —CH ₂ CH ₂ — or a single bond, and more preferably a single bond. n is 0 or 1, but is preferably 0. X ¹ and X ² are each independently —H, —F, —Cl, —CF ₃ , —OCH ₂ F, —OCHF ₂ , —OCF ₃ , —CH ₂ CF ₃ , _Cl, -CF _3, preferably _{-OCHF 2, -OCF 3, -F,} -CF 3, more preferably -OCF _3, F is particularly preferred.
[0019]
As a specific structure, the following general formula (Ia)
Embedded image

(Wherein R ¹ , A ¹ , Z ¹ and n represent the same meaning as in general formula (I)) is preferred, and the following compounds are particularly preferred,
[0020]
Embedded image

(In the formula, R ¹ represents an alkyl group having 1 to 8 carbon atoms or an alkoxyl group.) The following compounds are also preferable.
[0021]
Embedded image

(In the formula, ^{R 1} represents an alkyl group or an alkoxyl group having 1 to 8 carbon atoms.)
Among these compounds selected from the general formula (I), it is preferable that at least one composition contains a compound having a dielectric anisotropy (Δε) of 1.5 or more, more preferably 2 or more. preferable.
[0022]
As the second component, one or more compounds of the general formula (II) are contained, preferably 1 to 20 types, more preferably 1 to 15 types, particularly preferably 1 to 10 types, 1 to 5 types are particularly preferred. Moreover, 5 mass%-50 mass% are preferable, and, as for these content rates, 5 mass%-30 mass% are more preferable.
[0023]
In the general formula (II), R ² and R ³ are an unsubstituted linear alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, —CF ₃ , —OCH ₂ F, —OCHF ₂ , —OCF ₃ is preferable, unsubstituted linear alkyl group having 1 to 10 carbon atoms or alkenyl group having 2 to 10 carbon atoms, —CF ₃ , —OCHF ₂ , —OCF ₃ is more preferable, and unsubstituted linear chain Of these, an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 6 carbon atoms, —CF ₃ , and —OCF ₃ are particularly preferable.
R ² and R ³ may be the same or different, but R ² and R ³ in the same molecule are more preferably different. L ¹ and L ² are preferably —COO—, —OCO—, —CH ₂ CH ₂ —, —C≡C—, — (CH ₂ ) ₄ — or a single bond, and —CH ₂ CH ₂ —, —C ≡C— or a single bond is more preferable, —CH ₂ CH ₂ — or a single bond is particularly preferable. When a plurality of L ¹ and L ² are present, at least one is preferably a single bond. o is preferably 0 or 1.
[0024]
B ¹ , B ² and B ³ are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group or 3,5-difluoro-1, 4-phenylene group is preferable, trans-1,4-cyclohexylene group or 1,4-phenylene group is more preferable, and at least one of B ¹ , B ² and B ³ is trans-1,4-cyclohexylene It is preferably a group.
[0025]
The general formula (II) is preferably a structure represented by the following general formula (IIa) as a specific structure.
Embedded image

(In the formula, R ² and R ³ are an alkyl group or alkoxyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 3 to 16 carbon atoms, —CF ₃ , —OCH. ₂ F, —OCHF ₂ , —OCF ₃ , B ³ represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and r represents 0 or 1.)
It is preferable that the content rate of the compound of general formula (IIa) is the range of 5-50 mass%.
[0026]
A structure represented by the following general formula is also preferable.
Embedded image

(In the formula, R ⁵ and R ⁶ are an alkyl group or alkoxyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 3 to 16 carbon atoms, —CF ₃ , —OCH, ₂ F, —OCHF ₂ , —OCF ₃ ) are preferred.
[0027]
As the third component, one or more compounds of the general formula (III) are contained, preferably 1 to 20 types, more preferably 1 to 15 types, particularly preferably 1 to 10 types, 5 to 10 types are particularly preferred. Moreover, as for these content rates, 10 mass%-85 mass% are preferable.
[0028]
In general formula (III), R ⁴ is preferably an unsubstituted linear alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, and an unsubstituted linear alkyl group having 1 to 10 carbon atoms. Alternatively, an alkenyl group having 2 to 10 carbon atoms is more preferable, an unsubstituted linear alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 6 carbon atoms is particularly preferable, and in the alkenyl group, the formulas (a) to (e ) Is more preferable. K ¹ and K ² are —COO—, —OCO—, —CH ₂ CH ₂ —, —C≡C—, —OCF ₂ —, —CF ₂ O—, — (CH ₂ ) ₄ — or a single bond. _{preferably, -CH 2 CH 2 -, -} C≡C -, - OCF 2 -, - CF 2 O- or a single bond is more preferable, _{-CH 2} CH 2 - or a single bond is particularly preferred, ^{K 1} or ^{K 2} When a plurality of are present, at least one is preferably a single bond. p is preferably 1. C ¹ and C ² are each independently a trans-1,4-cyclohexylene group, 1,4-phenylene group, 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylene. Group is preferable, trans-1,4-cyclohexylene group or 1,4-phenylene group is more preferable, and trans-1,4-cyclohexylene group is particularly preferable.
[0029]
X ⁴ has the same definition as —H, —F, —Cl, —CN, —CF ₃ , —CHF ₂ , —OCH ₂ F, —OCHF ₂ , —OCF ₃ , —CH ₂ CF ₃ or R ^1. _{but, -F, -CN, -CF 3,} -CHF 2, -OCH 2 F, -OCHF 2, preferably -OCF _3, F is particularly preferred.
[0030]
General formula (III) has a specific structure as general formula (III-1)
Embedded image

(In the formula, R ⁷ represents an alkyl group having 1 to 8 carbon atoms or an alkoxyl group, and an alkenyl group having 2 to 8 carbon atoms, and L ⁵ and L ⁶ each independently represent —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, — (CH ₂ ) ₄ —, —OCF ₂ —, —CF ₂ O— or a single bond, ring I represents a 1,4-phenylene group or trans-1, 4-cyclohexylene group, X ⁹ represents H or F, and Y ⁴ represents —CN, —F, —Cl, —CF ₃ , —OCF ₃ or —OCHF ₂ ). .
[0031]
In addition, the general formula (III) has the following general formula as a specific structure:

[0032]
Embedded image

(In the formula, R ⁷ represents an alkyl group having 1 to 8 carbon atoms or an alkoxyl group, and an alkenyl group having 2 to 8 carbon atoms, X ³ and X ⁴ each independently represent H or F, and Y ⁴ is _{-CN, -F, -Cl, -CF 3} , structures represented by represented.) the -OCF ₃ or -OCHF ₂ are also preferred.
[0033]
The nematic liquid crystal composition of the present invention contains one or more compounds of the general formula (Ia), further contains one or more compounds of the general formula (II), and further contains a compound of the general formula (III). It is preferable to contain one or more compounds.
[0034]
In addition, the compound represented by the general formula (Ia) contains one or more compounds, the content is in the range of 5 to 50% by mass, and the compound represented by the general formula (IIa) is one or two kinds. The content is in the range of 10 to 50% by mass, and contains one or more compounds of the general formula (III), and the content is in the range of 5 to 80% by mass. It is preferable.
[0035]
Furthermore, 1 type-3 types of compounds represented with general formula (Ia) are contained, the content rate is the range of 10-40 mass%, and 1 type-5 types of compounds represented with general formula (II) are included. It contains seeds, the content is in the range of 5 to 30% by mass, contains 5 to 10 compounds represented by the general formula (III), and the content is 10 to 85% by mass. It is particularly preferable that the range is
[0036]
The nematic liquid crystal composition of the present invention has a wide liquid crystal phase temperature range (absolute value of the difference between the liquid crystal phase lower limit temperature and the liquid crystal phase upper limit temperature), but the liquid crystal phase temperature range is preferably 80 ° C. or higher, preferably 90 ° C. or higher. Is more preferable, and 100 ° C. or higher is particularly preferable. Further, the upper limit temperature of the liquid crystal phase is preferably 70 ° C. or higher, more preferably 80 ° C. or higher. Furthermore, the liquid crystal phase lower limit temperature is preferably −20 ° C. or lower, and more preferably −30 ° C. or lower.
[0037]
The nematic liquid crystal composition is useful for AM-LCDs and STN-LCDs, but is particularly useful for AM-LCDs, and can be used for transmissive or reflective liquid crystal display elements. The nematic liquid crystal composition of the present invention may contain a normal nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal and the like in addition to the above compounds.
[0038]
【Example】
EXAMPLES Hereinafter, although an Example is given and this invention is further explained in full detail, this invention is not limited to these Examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by mass”.
[0039]
In the examples, the measured characteristics are as follows.

[0040]
Embedded image

[0041]
(Example 1, Comparative Examples 1 and 2) Adjustment of liquid crystal composition Nematic liquid crystal compositions (No. 1), (R1) and (R2) shown below were adjusted, and their physical properties were measured. It is shown in 1.
[Table 1]

[0042]
As shown in Table 1, the nematic liquid crystal composition of Example 1 has a higher liquid crystal phase lower limit temperature (T _{→ N} ) than the nematic liquid crystal composition of Comparative Example 1, and the liquid crystal phase upper limit temperature (T _N− It can be seen that _I ) is low and has a wide liquid crystal temperature range.
Using this nematic liquid crystal composition, a TFT liquid crystal display device was prepared and its response speed was measured. The TFT liquid crystal device using the nematic liquid crystal composition of Example 1 was able to respond in 43 ms. The TFT liquid crystal device using the nematic liquid crystal composition of Example 1 had a response time of 47 ms, and Example 1 was superior.
[0043]
Similarly, the nematic liquid crystal composition of Example 1 has a lower liquid crystal phase lower limit temperature (T _{→ N} ) and a lower liquid crystal phase upper limit temperature (T _N-I ) than the nematic liquid crystal composition of Comparative Example 2. It can be seen that it has a wide liquid crystal temperature range.
The response time of the TFT liquid crystal element using the nematic liquid crystal composition of Comparative Example 2 was 45 ms, and Example 1 was superior.
[0044]
(Examples 2 and 3) Adjustment of liquid crystal composition Nematic liquid crystal compositions (No. 2) and (No. 3) shown below were prepared, their physical properties were measured, and the results are shown in Table 1.
[Table 2]

[0045]
As shown in Table 3, the nematic liquid crystal compositions of Examples 2 and 3 have a high liquid crystal phase lower limit temperature (T _{→ N} ), a lower liquid crystal phase upper limit temperature (T _N-I ), and a wider liquid crystal temperature range. I understand that I have it.
Using this nematic liquid crystal composition, a TFT liquid crystal display device having excellent display quality could be produced.
[0046]
【The invention's effect】
According to the nematic liquid crystal composition of the present invention, it is possible to provide a nematic liquid crystal composition using an indane compound and having a low liquid crystal phase lower limit temperature, a higher liquid crystal phase upper limit temperature, and a low viscosity.

Claims (9)

Formula (I)

Wherein R ¹ is a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 15 carbon atoms substituted with at least one halogen, an alkenyl group having 2 to 15 carbon atoms or at least one halogen. Represents a substituted alkenyl group having 2 to 15 carbon atoms, and one or two or more CH ₂ groups present in these groups are each independently —O—, wherein O atoms are not directly bonded to each other, May be replaced by -S-, -CO-, -COO-, -OCO- or -OCO-O-;
A ¹ is,
(A) trans-1,4-one CH ₂ group or nonadjacent two or more CH ₂ groups existing in xylene group (in this group the cycloalkyl is replaced by -O- and or -S- May be)
(B) 1,4-phenylene group (one CH ₂ group present in this group or two or more non-adjacent CH ₂ groups may be replaced by —N—)
A group selected from the group consisting of the above-mentioned groups (a) and (b) may be substituted with CN or halogen;
n is 0 or 1;
Z ¹ is —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, — (CH ₂ ) ₄ —, _{-CH = CH-CH 2 CH 2} -, - a CH 2 CH 2 -CH = CH- or a single bond,
Z ² is —CH ₂ CH ₂ —, —CH═CH— or a single bond,
X ¹ and X ² are each independently —H, —F, —Cl, —CF ₃ , —OCH ₂ F, —OCHF ₂ , —OCF ₃ , —CH ₂ CF ₃ . ) Containing one or more compounds selected from general formula (II)

(Wherein R ² and R ³ each independently represent the same meaning as R ¹ ,
B ¹ , B ² and B ³ are each independently (a) a trans-1,4-cyclohexylene group (one CH ₂ group present in this group or two or more CH ₂ not adjacent to each other). Group may be replaced by -O- and / or -S-)
(B) 1,4-phenylene group (one CH ₂ group present in this group or two or more non-adjacent CH ₂ groups may be replaced by —N—)
A group selected from the group consisting of the above-mentioned groups (a) and (b) may be substituted with CN or halogen;
o is 0, 1 or 2;
L ¹ and L ² are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O— or -C≡C-, and when there are a plurality of L ² and B ^3, they may be the same or different. And a compound selected from general formula (III)

(Wherein R ⁴ represents the same meaning as R ^1, and C ¹ and C ² are each independently
(A) trans-1,4-one CH ₂ group or nonadjacent two or more CH ₂ groups existing in xylene group (in this group the cycloalkyl is replaced by -O- and or -S- May be)
(B) 1,4-phenylene group (one CH ₂ group present in this group or two or more non-adjacent CH ₂ groups may be replaced by —N—)
A group selected from the group consisting of the above-mentioned groups (a) and (b) may be substituted with CN or halogen;
K ¹ and K ² are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O— or -C≡C-
X ³ and X ⁵ are each independently H or F;
p is 1 or 2,
X ⁴ has the same definition as —H, —F, —Cl, —CN, —CF ₃ , —OCH ₂ F, —OCHF ₂ , —OCF ₃ , —CH ₂ CF ₃ or R ¹ . 1) a nematic liquid crystal composition containing one or more compounds selected from: General formula (I) is general formula (Ia)

The nematic liquid crystal composition according to claim ¹ , wherein R ¹ , A ¹ , Z ¹ , and n have the same meaning as in general formula (I). The nematic liquid crystal composition according to claim 1 or 2, wherein the content of the compound of the general formula (I) or the general formula (Ia) is in the range of 5 to 50% by mass. As a compound of general formula (II), general formula (IIa)

(In the formula, R ² and R ³ are an alkyl group or alkoxyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 3 to 16 carbon atoms, —CF ₃ , —OCH. ₂ F, —OCHF ₂ , —OCF ₃ , B ³ represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and r represents 0 or 1. Item 4. The nematic liquid crystal composition according to item 1, 2 or 3. The nematic liquid crystal composition according to claim 4, wherein the content of the compound of the general formula (IIa) is in the range of 5 to 50% by mass. 2. The nematic liquid crystal composition according to claim 1, wherein the content of the compound of the general formula (III) is in the range of 10 to 85% by mass. 1 type or 2 types or more of compounds represented by general formula (Ia) are contained, the content rate is the range of 5-50 mass%, and also 1 type or 2 types or more of compounds of general formula (IIa) are included. And containing one or more compounds of the general formula (III) in a range of 5 to 40% by mass, and a content of 10 to 85% by mass. The nematic liquid crystal composition according to 3, 5, or 6. A liquid crystal display element using the nematic liquid crystal composition according to claim 1. An active matrix liquid crystal display element using the nematic liquid crystal composition according to claim 1.