JPH08217728A - Dimer-type optically active compound - Google Patents
Dimer-type optically active compoundInfo
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- JPH08217728A JPH08217728A JP20788395A JP20788395A JPH08217728A JP H08217728 A JPH08217728 A JP H08217728A JP 20788395 A JP20788395 A JP 20788395A JP 20788395 A JP20788395 A JP 20788395A JP H08217728 A JPH08217728 A JP H08217728A
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、二量体型の光学活性化
合物およびそれを用いた液晶組成物に関する。TECHNICAL FIELD The present invention relates to a dimer type optically active compound and a liquid crystal composition using the same.
【０００２】[0002]
【従来技術】液晶表示素子は、１）低電圧作動性、２）
低消費電力性、３）薄型表示、４）受光型などの優れた
特徴を有するため、ＴＮ形、ＳＴＮ形などのネマチック
液晶を用いた電気光学装置が数多く開発されている。ネ
マチック液晶では図１のＡで示される三角波として電圧
を印加したとき、図１のＢで示されるような光学応答を
示す。しかし、これら現在、広い範囲で利用されている
ネマチック液晶を用いたものは、いずれも応答速度が、
数ｍｓｅｃ〜数百ｍｓｅｃと極めて遅いため、その応用
分野に制限がある。ネマチック液晶を用いた素子の応答
速度が遅いのは、分子を動かすトルクが基本的に誘電率
の異方性に基づいているが、その力があまり強くないた
めである。2. Description of the Related Art Liquid crystal display devices have 1) low voltage operability and 2)
Many electro-optical devices using nematic liquid crystals such as TN type and STN type have been developed because they have excellent features such as low power consumption, 3) thin display, and 4) light receiving type. The nematic liquid crystal exhibits an optical response as shown by B in FIG. 1 when a voltage is applied as the triangular wave shown by A in FIG. However, these nematic liquid crystals, which are currently used in a wide range, all have response speeds
Since it is extremely slow at several msec to several hundred msec, its application field is limited. The reason that the response speed of the device using the nematic liquid crystal is slow is that the torque for moving the molecule is basically based on the anisotropy of the dielectric constant, but the force is not so strong.
【０００３】このため、応答性のすぐれた新しい液晶表
示方式の開発が進められており、光学応答時間がμｓｅ
ｃオーダーという、極めて短い超高速デバイスが可能に
なる強誘電性液晶の開発が試みられている。For this reason, a new liquid crystal display system having excellent responsiveness is being developed, and the optical response time is μse.
Attempts have been made to develop a ferroelectric liquid crystal of c-order, which enables an extremely short ultra-high speed device.
【０００４】強誘電性液晶は、１９７５年、Ｍｅｙｅｒ
等によりＤＯＢＡＭＢＣ（ｐ−デシルオキシ ベンジリ
デン−ｐ−アミノ−２−メチルブチルシンナメート）が
初めて合成された（Ｌｅ Ｊｏｕｒｎａｌ ｄｅ Ｐｈ
ｙｓｉｑｕｅ， ３６巻 １９７５ Ｌ−６９．）。さ
らに、１９８０年ＣｌａｒｋとＬａｇａｒｗａｌｌによ
り、ＤＯＢＡＭＢＣのサブマイクロ秒の高速応答、メモ
リー特性などの表示デバイス上の特性が報告されて以
来、強誘電性液晶は、大きな注目を集めるようになった
〔Ｎ．Ａ．Ｃｌａｒｋ， ｅｔａｌ．， Ａｐｐｌ．
Ｐｈｙｓ． Ｌｅｔｔ． ３６． ８９９（１９８
０）〕。そして、強誘電性液晶では、図１のＡで示され
る三角波電圧を印加したとき、図１のＣで示されるよう
な光学応答を示すことが理想とされている。Ferroelectric liquid crystals were first described in 1975 by Meyer.
DOBAMBC (p-decyloxybenzylidene-p-amino-2-methylbutyl cinnamate) was synthesized for the first time by (Le Journal de Ph)
ysique, 36 volumes 1975 L-69. ). Furthermore, since 1980 Clark and Lagarwall reported on the characteristics of display devices such as sub-microsecond high-speed response of DOBAMBC and memory characteristics, ferroelectric liquid crystals have attracted great attention [N. A. Clark, et al. , Appl.
Phys. Lett. 36. 899 (198
0)]. It is ideal that the ferroelectric liquid crystal exhibits an optical response as shown by C in FIG. 1 when a triangular wave voltage shown by A in FIG. 1 is applied.
【０００５】しかし、彼らの方式には、実用化に向けて
多くの技術的課題があり、表示ディスプレーに不可欠な
液晶分子の配向制御に有効かつ実用的な方法も確立され
ていなかった。However, their method has many technical problems for practical use, and an effective and practical method for controlling the alignment of liquid crystal molecules, which is indispensable for display, has not been established.
【０００６】この報告以来、液晶材料／デバイス両面か
らの様々な試みがなされ、ツイスト二状態間のスイッチ
ングを利用した表示デバイスが試作され、それを用いた
高速電気光学装置も例えば特開昭５６−１０７２１６号
などで提案されているが、高いコントラストや適正なし
きい値特性は得られていない。Since this report, various attempts have been made from both sides of the liquid crystal material / device, a display device utilizing switching between twisted two states has been prototyped, and a high speed electro-optical device using the same has been disclosed in, for example, Japanese Patent Laid-Open No. 56-56. No. 107216, etc., but high contrast and proper threshold characteristics have not been obtained.
【０００７】このような視点から他のスイッチング方式
についても探索され、過渡的な散乱方式が提案された。
その後、１９８８年に萩原らによる三安定状態を有する
液晶の三状態スイッチング方式が報告された〔Ａ．Ｄ．
Ｌ．Ｃｈａｎｄａｎｉ，Ｔ．Ｈａｇｉｗａｒａ，Ｙ．Ｓ
ｕｚｕｋｉ ｅｔａｌ．，Ｊａｐａｎ．Ｊ．ｏｆ Ａｐ
ｐｌ．Ｐｈｙｓ．，２７，（５），Ｌ７２９−Ｌ７３２
（１９８８）〕。From this point of view, other switching systems have been searched and a transient scattering system has been proposed.
Then, in 1988, Hagiwara et al. Reported a three-state switching method for a liquid crystal having three stable states [A. D.
L. Chandani, T .; Hagiwara, Y .; S
uzuki et al. , Japan. J. of Ap
pl. Phys. , 27, (5), L729-L732
(1988)].
【０００８】前記「三状態を有する」とは、第一の電極
基板と所定の間隙を隔てて配置されている第二の電極基
板の間に強誘電性液晶が挟まれてなる液晶電気光学装置
において、前記第一及び第二の電極基板に電界形成用の
電圧が印加されるよう構成されており、図１Ａで示され
る三角波として電圧を印加したとき、図１Ｄのように前
記強誘電性液晶が、無電界時に分子配向が第一の安定状
態（図１Ｄの）を有し、かつ、電界印加時に一方の電
界方向に対し分子配向が前記第一の安定状態とは異なる
第二の安定状態（図１Ｄの）を有し、さらに他方の電
界方向に対し前記第一及び第二の安定状態とは異なる第
三の分子配向安定状態（図１Ｄの）を有することを意
味する。なお、この三安定状態、すなわち三状態を利用
する液晶電気光学装置については、本出願人は特願昭６
３−７０２１２号として出願し、特開平２−１５３３２
２号として公開されている。The above-mentioned "having three states" means a liquid crystal electro-optical device in which a ferroelectric liquid crystal is sandwiched between a first electrode substrate and a second electrode substrate which is arranged with a predetermined gap. 1 is configured so that a voltage for forming an electric field is applied to the first and second electrode substrates, and when the voltage is applied as a triangular wave shown in FIG. However, the molecular orientation has a first stable state (in FIG. 1D) when no electric field is applied, and the second stable state in which the molecular orientation is different from the first stable state with respect to one electric field direction when an electric field is applied. (In FIG. 1D), and further has a third molecular orientation stable state (in FIG. 1D) different from the first and second stable states with respect to the other electric field direction. Regarding the liquid crystal electro-optical device utilizing the tri-stable state, that is, the tri-state, the present applicant filed Japanese Patent Application No.
Japanese Patent Application Laid-Open No. 2-153332
It is published as Issue 2.
【０００９】三安定状態を示す反強誘電性液晶の特徴を
さらに詳しく説明する。クラーク／ラガウェル（Ｃｌａ
ｒｋ−Ｌａｇａｗａｌｌ）により提案された表面安定化
強誘電性液晶素子では、キラルスメクチックＣ（ＳｍＣ
＊）相において強誘電性液晶分子が図２Ａ（ａ），
（ｂ）のように一方向に均一配向した２つの安定状態を
示し、印加電界の方向により、どちらか一方の状態に安
定化され、電界を切ってもその状態が保持される。The characteristics of the antiferroelectric liquid crystal exhibiting the tristable state will be described in more detail. Clark / Ragawell (Cla
In the surface-stabilized ferroelectric liquid crystal device proposed by rk-Lagawall, chiral smectic C (SmC
In the *) phase, the ferroelectric liquid crystal molecules are shown in FIG. 2A (a),
As shown in (b), it shows two stable states that are uniformly oriented in one direction. Depending on the direction of the applied electric field, it is stabilized in either one of the states, and the state is maintained even when the electric field is cut off.
【００１０】しかしながら実際には、強誘電性液晶分子
の配向状態は、液晶分子のダイレクターが捩れたツイス
ト二状態を示したり、層がくの字に折れ曲ったシエブロ
ン構造を示す。シエブロン層構造では、スイッチング角
が小さくなり低コントラストの原因になるなど、実用化
へ向けて大きな障害になっている。一方、三安定状態を
示す“反”強誘電性液晶では、上記液晶電気光学装置に
おいて、無電界時には、図２Ｂ（ａ）に示すごとく隣り
合う層毎に分子は逆方向に傾き反平行に配列し、液晶分
子の双極子はお互に打ち消し合っている。したがって、
液晶層全体として自発分極は打ち消されている。この分
子配列を示す液晶相は、図１Ｄのに対応している。In reality, however, the alignment state of the ferroelectric liquid crystal molecules shows a twisted two-state in which the director of the liquid crystal molecules is twisted, or a chevron structure in which the layers are bent in a V shape. With the Sieblon layer structure, the switching angle becomes small, which causes low contrast, which is a major obstacle to practical use. On the other hand, in the “anti” ferroelectric liquid crystal exhibiting the tristable state, in the liquid crystal electro-optical device, when there is no electric field, the molecules are arranged in antiparallel to each other in the adjacent layers as shown in FIG. 2B (a). However, the dipoles of the liquid crystal molecules cancel each other out. Therefore,
Spontaneous polarization is canceled in the entire liquid crystal layer. The liquid crystal phase showing this molecular arrangement corresponds to that in FIG. 1D.
【００１１】さらに、（＋）又は（−）のしきい値より
充分大きい電圧を印加すると、図２Ｂ（ｂ）および
（ｃ）に示す液晶分子が同一方向に傾き、平行に配列す
る。この状態では、分子の双極子も同一方向に揃うため
自発分極が発生し、強誘電相となる。すなわち、“反”
強誘電性液晶においては、無電界時の“反”強誘電相と
印加電界の極性による２つの強誘電相が安定になり、
“反”強誘電相と２つの強誘電相間を直流的しきい値を
持って三安定状態間スイッチングを行うものである。こ
のスイッチングに伴う液晶分子配列の変化により図３に
示すダブル・ヒステリシスを描いて光透過率が変化す
る。このダブル・ヒステリシスに、図３の（ｂ）に示す
ようにバイアス電圧を印加して、さらにパルス電圧を重
畳することによりメモリー効果を実現できる特徴を有す
る。Further, when a voltage sufficiently higher than the threshold value of (+) or (-) is applied, the liquid crystal molecules shown in FIGS. 2B and 2C are tilted in the same direction and arranged in parallel. In this state, the dipoles of the molecules are also aligned in the same direction, so spontaneous polarization occurs and a ferroelectric phase is formed. That is, "anti"
In a ferroelectric liquid crystal, the "anti" ferroelectric phase when there is no electric field and the two ferroelectric phases due to the polarity of the applied electric field are stable,
It performs switching between tristable states with a DC threshold between the "anti" ferroelectric phase and two ferroelectric phases. Due to the change in the liquid crystal molecule alignment accompanying this switching, the light transmittance changes with the double hysteresis shown in FIG. A memory effect can be realized by applying a bias voltage to the double hysteresis as shown in FIG. 3B and further superimposing a pulse voltage on the double hysteresis.
【００１２】さらに、電界印加により強誘電相は層がス
トレッチされ、ブックシエルフ構造となる。一方、第三
安定状態の“反”強誘電相では類似ブックシエルフ構造
となる。この電界印加による層構造スイッチングが液晶
層に動的シエアーを与えるため駆動中に配向欠陥が改善
され、良好な分子配向が実現できる。そして、“反”強
誘電性液晶では、プラス側とマイナス側の両方のヒステ
リシスを交互に使い画像表示を行なうため、自発分極に
基づく内部電界の蓄積による画像の残像現象を防止する
ことができる。Further, by applying an electric field, the layer of the ferroelectric phase is stretched to form a Bookshelf structure. On the other hand, in the "anti" ferroelectric phase in the third stable state, it has a similar Bookshelf structure. Since the layer structure switching by the application of the electric field gives a dynamic shear to the liquid crystal layer, alignment defects are improved during driving, and good molecular alignment can be realized. In the "anti" ferroelectric liquid crystal, since the image display is performed by alternately using the hysteresis on both the positive side and the negative side, it is possible to prevent the afterimage phenomenon of the image due to the accumulation of the internal electric field due to the spontaneous polarization.
【００１３】以上のように、“反”強誘電性液晶は、
１）高速応答が可能で、２）高いコントラストと広い視
野角および３）良好な配向特性とメモリー効果が実現で
きる、非常に有用な液晶化合物と言える。As described above, the "anti" ferroelectric liquid crystal is
It can be said that it is a very useful liquid crystal compound that can realize 1) high-speed response, 2) high contrast and wide viewing angle, and 3) good alignment characteristics and memory effect.
【００１４】三安定状態を示す液晶相については、１）
Ａ．Ｄ．Ｌ．Ｃｈａｎｄａｎｉ ｅｔａｌ.，Ｊａｐａ
ｎ Ｊ．Ａｐｐｌ．Ｐｈｙｓ.，２８，Ｌ−１２６５
（１９８９）、２）Ｈ．Ｏｒｉｈａｒａ ｅｔａｌ.，
Ｊａｐａｎ Ｊ．Ａｐｐｌ．Ｐｈｙｓ.，２９，Ｌ−３
３３（１９９０）に報告されており、“反”強誘電的性
質にちなみＳｍＣ＊Ａ相（Ａｎｔｉｆｅｒｒｏｅｌｅｃ
ｔｒｉｃ ＳｍｅｃｔｉｃＣ＊相）と命名している。Regarding the liquid crystal phase showing the tristable state, 1)
A. D. L. Chandani et al., Japan
nJ. Appl. Phys., 28 , L-1265.
(1989), 2) H.M. Orihara et al.,
Japan J. Appl. Phys., 29 , L-3
33 (1990), the SmC * A phase (Antiferreroelec) associated with the "anti" ferroelectric property.
tric Sticc C * phase).
【００１５】三安定状態を示す“反”強誘電相を相系列
に有する液晶化合物は、本発明者の出願した特開平１−
３１６３６７号、特開平１−３１６３７２号、特開平１
−３１６３３９号、特開平２−２８１２８号及び市橋等
の特開平１−２１３３９０号公報があり、また三安定状
態を利用した液晶電気光学装置としては本出願人は特開
平２−４０６２５号、特開平２−１５３３２２号、特開
平２−１７３７２４号において新しい提案を行ってい
る。A liquid crystal compound having an "anti" ferroelectric phase showing a tristable state in a phase series is disclosed in Japanese Patent Application Laid-Open No.
316367, JP-A-1-316372, JP-A-1
-316339, JP-A-2-28128, and JP-A-1-213390 of Ichihashi, etc., and as the liquid crystal electro-optical device utilizing the tristable state, the present applicant has JP-A-2-40625 and JP-A-2-40625. No. 2-153322 and Japanese Patent Laid-Open No. 2-173724 make new proposals.
【００１６】“反”強誘電性液晶を液晶ディスプレイへ
応用する場合、１）動作温度範囲、２）応答速度、３）
自発分極、４）ヒステリシス特性等を単一液晶で全て満
足させることは困難であり、通常十数種類の混合液晶と
して調製される。When an "anti" ferroelectric liquid crystal is applied to a liquid crystal display, 1) operating temperature range, 2) response speed, 3)
It is difficult to satisfy all the spontaneous polarization, 4) hysteresis characteristics, etc. with a single liquid crystal, and it is usually prepared as a mixed liquid crystal of ten or more kinds.
【００１７】しかしながら、１）駆動温度範囲、２）ヒ
ステリシス特性、３）駆動特性の温度依存性など、実用
上に必要な駆動性能を満足する反強誘電性液晶材料はま
だ開発されておらず、高精細な画像を表示するディスプ
レイの実用化が遅れている。特に、三安定状態を示す反
強誘電性液晶表示素子の性能は、反強誘電性液晶固有の
物性であるヒステリシスの形状に大きく依存する。図３
に示すように、実用上十分な画像保持特性の指標となる
メモリーマージン〔Ｍ＝（Ｖ3−Ｖ2）／（Ｖ4−Ｖ3）〕
と急峻性〔α＝Ｖ4／Ｖ3〕を示す材料は、現在のところ
未だ報告されていない。実用上必要とされるヒステリシ
ス形状を有する反強誘電性液晶材料の開発およびその改
善技術の提供が強く要望されている。However, an antiferroelectric liquid crystal material satisfying the driving performance required for practical use, such as 1) driving temperature range, 2) hysteresis characteristics, 3) temperature dependence of driving characteristics, has not yet been developed, Practical application of a display for displaying a high-definition image is delayed. In particular, the performance of an antiferroelectric liquid crystal display device exhibiting a tristable state largely depends on the shape of hysteresis, which is a physical property unique to antiferroelectric liquid crystals. FIG.
As shown in, the memory margin [M = (V 3 −V 2 ) / (V 4 −V 3 )] which is an index of the image holding characteristic that is practically sufficient.
And a material exhibiting steepness [α = V 4 / V 3 ] have not been reported so far. There is a strong demand for the development of an antiferroelectric liquid crystal material having a hysteresis shape that is required for practical use and the provision of an improvement technique therefor.
【００１８】一方、１つの分子中に不斉炭素を二つ有す
るダブルキラル型液晶は、１９９１年のＰｈｙｓ．Ｒｅ
ｖ．Ｌｅｔｔ．６６（１９９１）２８９１において、１
−メチル−ヘプチル−テレフタリデン−ビス−アンモシ
アネート（ＭＨＴＡＣ）に関する報告があるが、本発明
のような光学活性部位をアルキレン鎖により直接結合し
た二量体型光学活性化合物は全く未知の化合物である。On the other hand, a double chiral type liquid crystal having two asymmetric carbon atoms in one molecule is described in Phys. Re
v. Lett. 66 (1991) 2891, 1
Although there is a report on -methyl-heptyl-terephthalidene-bis-ammocyanate (MHTAC), a dimer type optically active compound in which an optically active site as in the present invention is directly bonded by an alkylene chain is a completely unknown compound.
【００１９】[0019]
【発明が解決しようとする課題】本発明の第一の目的
は、新規な二量体型光学活性化合物を提供する点にあ
る。本発明の第二の目的は、電気光学素子や液晶ディス
プレイなどに応用が期待できる前記二量体型光学活性化
合物を含有する液晶組成物および液晶素子を提供する点
にある。The first object of the present invention is to provide a novel dimer type optically active compound. A second object of the present invention is to provide a liquid crystal composition and a liquid crystal element containing the dimer type optically active compound, which can be expected to be applied to electro-optical elements and liquid crystal displays.
【００２０】[0020]
【課題を解決するための手段】本発明の第１は、下記一
般式〔Ｉ〕The first aspect of the present invention is to provide the following general formula [I]
【化２】 〔式中、Ｒ1、Ｒ3は置換基をそれぞれ有することもある
炭素数１〜１８のアルキル基よりなる群からそれぞれ独
立して選ばれた基であるが、炭素数６〜１４のアルキル
基が好ましい。Ｒ2、Ｒ4はＣＦ3およびＣＨ3よりなる群
からそれぞれ独立して選ばれた基である。Ｘ1、Ｘ2は単
結合、−Ｏ−、−ＣＯＯ−、−ＯＣＯ−および−ＯＣＯ
Ｏ−よりなる群からそれぞれ独立して選ばれた基であ
る。Ｙ1、Ｙ2およびＺ1、Ｚ2は単結合、−ＣＯＯ−、−
ＯＣＯ−、−ＣＨ2Ｏ−、−ＯＣＨ2−、−Ｃ≡Ｃ−より
なる群からそれぞれ独立して選ばれた基であるが、単結
合または−ＣＯＯ−が好ましい。環Ａ1、環Ａ2、環
Ｂ1、環Ｂ2、環Ｃ1および環Ｃ2は１個または２個のフッ
素原子で置換されていてもよい１，４−フェニレン基、
トランス−１，４−シクロヘキシレン基、ピリミジン−
２，５−ジイル基、ピリジン−２，５−ジイル基および
２，６−ナフチレン基よりなる群からそれぞれ独立して
選ばれた基であるが、Ｙ1が単結合の場合には環Ａ1また
は環Ｂ1の少なくとも一方が１，４−フェニレン基であ
ることが好ましく、Ｙ2が単結合の場合には環Ａ2または
環Ｂ2の少なくとも一方が１，４−フェニレン基である
ことが好ましく、Ｚ1が単結合の場合には環Ｂ1または環
Ｃ1の少なくとも一方が１，４−フェニレン基であるこ
とが好ましく、Ｚ2が単結合の場合には環Ｂ2または環Ｃ
2の少なくとも一方が１，４−フェニレン基であること
が好ましい。ｍは７〜２０の整数であるが、特に奇数が
好ましい。ｎ1、ｎ2は１および０よりなる群からそれぞ
れ独立して選ばれた整数である。＊は不斉炭素を示し、
その絶対配置は（Ｒ，Ｒ）、（Ｓ，Ｓ）、（Ｒ，Ｓ）ま
たは（Ｓ，Ｒ）であるが、Ｒ2とＲ3が等しい場合はその
絶対配置は（Ｒ，Ｒ）または（Ｓ，Ｓ）であることが好
ましい。〕で示される化合物であることを特徴とする二
量体型光学活性化合物に関する。Embedded image [In the formula, R 1 and R 3 are groups independently selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, which may have a substituent, respectively. Is preferred. R 2 and R 4 are groups independently selected from the group consisting of CF 3 and CH 3 . X 1 and X 2 are a single bond, -O-, -COO-, -OCO- and -OCO.
It is a group independently selected from the group consisting of O-. Y 1 , Y 2 and Z 1 , Z 2 are a single bond, —COO—, —
OCO -, - CH 2 O - , - OCH 2 -, - C≡C- is a independently selected groups from the group consisting of a single bond or -COO- are preferred. Ring A 1 , ring A 2 , ring B 1 , ring B 2 , ring C 1 and ring C 2 are a 1,4-phenylene group optionally substituted with one or two fluorine atoms,
Trans-1,4-cyclohexylene group, pyrimidine-
A group independently selected from the group consisting of a 2,5-diyl group, a pyridine-2,5-diyl group and a 2,6-naphthylene group, but when Y 1 is a single bond, a ring A 1 Alternatively, at least one of ring B 1 is preferably a 1,4-phenylene group, and when Y 2 is a single bond, at least one of ring A 2 or ring B 2 is a 1,4-phenylene group. Preferably, when Z 1 is a single bond, at least one of ring B 1 or ring C 1 is a 1,4-phenylene group, and when Z 2 is a single bond, ring B 2 or ring C 1
At least one of 2 is preferably a 1,4-phenylene group. m is an integer of 7 to 20, but an odd number is particularly preferable. n 1 and n 2 are integers independently selected from the group consisting of 1 and 0. * Indicates an asymmetric carbon,
Its absolute configuration is (R, R), (S, S), (R, S) or (S, R), but when R 2 and R 3 are equal, its absolute configuration is (R, R) or It is preferably (S, S). ] It is related with the compound shown by these, It relates to a dimer type optically active compound characterized by the above-mentioned.
【００２１】本発明の第２は、前記一般式〔Ｉ〕で示さ
れる二量体型光学活性化合物を含有することを特徴とす
る液晶組成物に関する。A second aspect of the present invention relates to a liquid crystal composition containing a dimer type optically active compound represented by the above general formula [I].
【００２２】本発明の第３は、前記液晶組成物を用いた
ことを特徴とする液晶表示素子に関する。A third aspect of the present invention relates to a liquid crystal display device characterized by using the above liquid crystal composition.
【００２３】二量体型液晶では分子の中央部分にあるア
ルキル鎖の長さに応じて、分子全体の形が規定される。
すなわちアルキル鎖を形成する炭素数が奇数個のときに
は一つの分子のまん中で折れ曲がる、“くの字構造”を
とる。このため隣接する層をまたがって分子が逆方向を
向くことになり、結果として反強誘電的な分子の配列構
造をとることになる。また偶数個の時には直線的な構造
になるか（Ｃ＝８個）、あるいは“くの字構造”をとる
（Ｃ＝１２個）かは炭素数に依存することになる。 二
量体型液晶において“くの字構造”をとる場合には双極
子モーメントの対形成ではなく、共有結合により反強誘
電的な分子の配列構造をとるわけであるから、その構造
は非常に安定である。In the dimer type liquid crystal, the shape of the whole molecule is defined according to the length of the alkyl chain in the central part of the molecule.
That is, when the number of carbon atoms forming the alkyl chain is an odd number, the molecule has a “doglegged structure” that bends in the middle of one molecule. For this reason, the molecules are directed in the opposite direction across the adjacent layers, and as a result, an antiferroelectric molecule arrangement structure is obtained. Whether the structure is linear (C = 8) or has a "doglegged structure" (C = 12) when the number is even depends on the number of carbon atoms. In the dimer-type liquid crystal, when the "dogleg structure" is adopted, the antiferroelectric molecules are arranged by covalent bonds, not by pair formation of dipole moments. Therefore, the structure is very stable. Is.
【００２４】本発明の一般式〔Ｉ〕の化合物は、下記一
般式で示される光学活性ジオール化合物〔II〕The compound of the general formula [I] of the present invention is an optically active diol compound [II] represented by the following general formula.
【化３】 （式中、Ｒ2、Ｒ4、ｍおよび＊は、式〔Ｉ〕におけるも
のと同一の内容を表わす。）と、下記一般式で示される
カルボン酸誘導体〔III−１〕Embedded image (In the formula, R 2 , R 4 , m and * represent the same contents as those in the formula [I].) And a carboxylic acid derivative [III-1] represented by the following general formula.
【化４】 （前記２つの式中、Ｒ1、Ｒ3、ｎ1、ｎ2、環Ａ1、環
Ａ2、環Ｂ1、環Ｂ2、環Ｃ1、環Ｃ2、Ｘ1、Ｘ2、Ｙ1、Ｙ
2、Ｚ1およびＺ2は、式〔Ｉ〕におけるものと同一の内
容を表わす。）をポリリン酸エチルやジシクロヘキシル
カルボジイミド等の脱水縮合剤を用いて反応させるか、
または前記カルボン酸誘導体〔III−１〕および／また
は〔III−２〕を酸ハロゲン化物に変換した後、塩基の
存在下、前記光学活性ジオール化合物〔II〕と反応させ
ることにより製造することができる。なお、前記カルボ
ン酸誘導体〔III−１〕と〔III−２〕は同一化合物であ
ることができ、また、前記光学活性ジオール化合物〔I
I〕のＲ2とＲ4は同一であることができる。〔III−１〕
と〔III−２〕および〔II〕のＲ2とＲ4のすべてが同一
のときの生成物〔Ｉ〕は、（ＣＨ2）ｍを中心として左
右対称の化合物となる。[Chemical 4] (In the above two formulas, R 1 , R 3 , n 1 , n 2 , ring A 1 , ring A 2 , ring B 1 , ring B 2 , ring C 1 , ring C 2 , X 1 , X 2 , Y 1 , Y
2 , Z 1 and Z 2 have the same meanings as in formula [I]. ) Is reacted with a dehydrating condensing agent such as ethyl polyphosphate or dicyclohexylcarbodiimide, or
Alternatively, it can be produced by converting the carboxylic acid derivative [III-1] and / or [III-2] into an acid halide and then reacting with the optically active diol compound [II] in the presence of a base. . The carboxylic acid derivatives [III-1] and [III-2] may be the same compound, and the optically active diol compound [I
R 2 and R 4 in I] can be the same. [III-1]
And [III-2] and [II] in which R 2 and R 4 are all the same, the product [I] is a compound having left-right symmetry about (CH 2 ) m.
【００２５】ここで、前記〔II〕の光学活性ジオール
は、下記一般式〔IV〕Here, the optically active diol of the above [II] is represented by the following general formula [IV]
【化５】 （式中、ｍは、式〔Ｉ〕におけるものと同一の内容を表
わす。）で表わされるジブロモアルカン化合物をリチウ
ムやマグネシウムを用いて有機金属化合物とした後、ヨ
ウ化銅などの銅反応剤を触媒として下記一般式で示され
る光学活性オキシラン〔Ｖ−１〕Embedded image (In the formula, m has the same meaning as in formula [I].) The dibromoalkane compound represented by the formula [I] is converted to an organometallic compound using lithium or magnesium, and then a copper reactant such as copper iodide is added. As a catalyst, an optically active oxirane represented by the following general formula [V-1]
【化６】 （前記２つの式中、Ｒ2、Ｒ4および＊は式〔Ｉ〕におけ
るものと同一の内容を表わす。）と反応させることによ
って製造することができる。前記光学活性オキシランは
一部市販されている。[Chemical 6] (In the above two formulas, R 2 , R 4 and * have the same meanings as those in formula [I]). Some of the optically active oxiranes are commercially available.
【００２６】また、前記一般式〔III−１〕、〔III−
２〕で表わされるカルボン酸誘導体は、液晶化合物の合
成中間体としてよく知られており、製造および入手は容
易である。Further, the above general formulas [III-1] and [III-
The carboxylic acid derivative represented by 2] is well known as a synthetic intermediate for liquid crystal compounds, and is easily manufactured and available.
【００２７】一方、一般式〔Ｉ〕において、Ｚ1および
Ｚ2が−ＣＯＯ−の場合には、以下の方法によっても製
造することができる。すなわち、前記光学活性ジオール
〔II〕と下記一般式で示されるカルボン酸〔VI−１〕On the other hand, in the general formula [I], when Z 1 and Z 2 are —COO—, they can also be produced by the following method. That is, the optically active diol [II] and a carboxylic acid [VI-1] represented by the following general formula:
【化７】 （前記２つの式中、環Ｃ1、環Ｃ2は、式〔Ｉ〕における
ものと同一の内容を表わす。）を脱水縮合剤を用いて反
応させるか、または、光学活性ジオールとカルボン酸
〔VII−１〕[Chemical 7] (In the above two formulas, ring C 1 and ring C 2 have the same meanings as those in formula [I]) using a dehydration condensing agent, or an optically active diol and a carboxylic acid [ VII-1]
【化８】 （前記２つの式中、環Ｃ1、環Ｃ2は、式〔Ｉ〕における
ものと同一の内容を表わし、Ｒは水酸基の保護基であ
り、例えばベンジル基などのアリールメチル基、メチル
基、エチル基などの低級アルキル基、メトキシメチル基
などの低級アルコキシメチル基、アセチル基などのアル
キル基、メトキシカルボニル基などの低級アルコキシカ
ルボニル基、テトラピラニル基などを表わす。）を脱水
縮合剤を用いて反応させるか、酸ハロゲン化物に変換し
たのち塩基存在下反応させ、さらに保護基を除去して、
化合物〔VIII〕Embedded image (In the above two formulas, ring C 1 and ring C 2 have the same meanings as in formula [I], R is a hydroxyl-protecting group, and examples thereof include an arylmethyl group such as a benzyl group, a methyl group, A lower alkyl group such as an ethyl group, a lower alkoxymethyl group such as a methoxymethyl group, an alkyl group such as an acetyl group, a lower alkoxycarbonyl group such as a methoxycarbonyl group, a tetrapyranyl group, etc.) using a dehydration condensing agent Or convert to an acid halide and then react in the presence of a base to further remove the protecting group,
Compound [VIII]
【化９】 （式中、環Ｃ1、環Ｃ2、Ｒ2、Ｒ4、ｍおよび＊は、式
〔Ｉ〕におけるものと同一の内容を表わす。）を製造す
る。[Chemical 9] (Wherein ring C 1 , ring C 2 , R 2 , R 4 , m and * have the same meanings as in formula [I]).
【００２８】この化合物〔VIII〕と下記一般式で示され
るカルボン酸〔IX−１〕This compound [VIII] and a carboxylic acid represented by the following general formula [IX-1]
【化１０】 （前記２つの式中、Ｒ1、Ｒ3、ｎ1、ｎ2、環Ａ1、環
Ａ2、環Ｂ1、環Ｂ2、Ｘ1、 Ｘ2、Ｙ1およびＹ2は、
式〔Ｉ〕におけるものと同一の内容を表わす。）をポリ
リン酸エチルやジシクロヘキシルカルボジイミド等の脱
水縮合剤を用いて反応させるか、または前記カルボン酸
〔IX−１〕および〔IX−２〕を酸ハロゲン化物に変換し
た後、塩基存在下、光学活性ジオール化合物〔VIII〕と
反応させることにより、Ｚ1およびＺ2が−ＣＯＯ−の場
合の一般式〔Ｉ〕の化合物を得ることができる。[Chemical 10] (In the above two formulas, R 1 , R 3 , n 1 , n 2 , ring A 1 , ring A 2 , ring B 1 , ring B 2 , X 1 , X 2 , Y 1 and Y 2 are
It has the same meaning as in formula [I]. ) Is reacted with a dehydration condensing agent such as ethyl polyphosphate or dicyclohexylcarbodiimide, or the carboxylic acids [IX-1] and [IX-2] are converted into acid halides, and then optically active in the presence of a base. By reacting with a diol compound [VIII], a compound of the general formula [I] when Z 1 and Z 2 are —COO— can be obtained.
【００２９】一般式〔IX−１〕、〔IX−２〕で表わされ
るカルボン酸は、液晶化合物の合成中間体としてよく知
られており、製造および入手は容易である。The carboxylic acids represented by the general formulas [IX-1] and [IX-2] are well known as synthetic intermediates for liquid crystal compounds and are easy to produce and obtain.
【００３０】本発明の化合物におけるＲ1、Ｒ3、−（環
Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および−（環Ａ
2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−の具体例を挙げる
が、本発明はこれに限定されるものではない。In the compounds of the present invention, R 1 , R 3 ,-(ring A 1 -Y 1 ) n 1 -ring B 1 -Z 1 -ring C 1-, and-(ring A
2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - Specific examples, but the present invention is not limited thereto.
【００３１】Ｒ1およびＲ3としては、置換基を有するこ
ともあるメチル基、エチル基、プロピル基、ブチル基、
ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノ
ニル基、デシル基、ウンデシル基、ドデシル基、トリデ
シル基、テトラデシル基、ペンタデシル基、ヘキサデシ
ル基、ヘプタデシル基およびオクタデシル基などが挙げ
られる。その置換基としては、メチル基、エチル基およ
びプロピル基などのアルキル基、メトキシ基、エトキシ
基、プロポキシ基、ブトキシ基、ペンチルオキシ基、ヘ
キシルオキシ基、ヘプチルオキシ基、オクチルオキシ
基、ノニルオキシ基およびデシルオキシ基などのアルコ
キシル基、ビニル基、１−プロペニル基および１−ブテ
ニル基などのアルケニル基、エチニル基および１−プロ
ピニル基などのアルキニル基、アセトキシ基、エタノイ
ルオキシ基、プロパノイルオキシ基、ブタノイルオキシ
基、ペンタノイルオキシ基およびヘキサノイルオキシ基
などのアルカノイル基、フッ素および塩素のハロゲン基
などが挙げられる。ただし、Ｘ1が−Ｏ−、−ＯＣＯ−
または−ＯＣＯＯ−の場合のＲ1の１位およびＸ2が−Ｏ
−、−ＯＣＯ−または−ＯＣＯＯ−の場合のＲ3の１位
にアルコキシ基、アルカノイル基およびハロゲン基が置
換しないことが好ましい。R 1 and R 3 are a methyl group which may have a substituent, an ethyl group, a propyl group, a butyl group,
Examples thereof include a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group and an octadecyl group. As the substituent, an alkyl group such as a methyl group, an ethyl group and a propyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group and Alkoxyl group such as decyloxy group, vinyl group, alkenyl group such as 1-propenyl group and 1-butenyl group, alkynyl group such as ethynyl group and 1-propynyl group, acetoxy group, ethanoyloxy group, propanoyloxy group, pig Examples thereof include an alkanoyl group such as a noyloxy group, a pentanoyloxy group and a hexanoyloxy group, and a halogen group such as fluorine and chlorine. However, X 1 is -O-, -OCO-
Or in the case of -OCOO-, the 1-position of R 1 and X 2 are -O.
In the case of-, -OCO- or -OCOO-, it is preferable that the 1-position of R 3 is not substituted with an alkoxy group, an alkanoyl group or a halogen group.
【００３２】−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1
−、および−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−
としては、以下のものが挙げられる。ｎ1が１、Ｙ1が単
結合、Ｚ1が−ＣＯＯ−の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1
−Ｚ1−環Ｃ1−、およびｎ2が１、Ｙ2が単結合、Ｚ2が
−ＣＯＯ−の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2
−としては、-(Ring A 1 -Y 1 ) n 1 -ring B 1 -Z 1 -ring C 1
-, and - (Ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 -
The following may be mentioned as examples. n 1 is 1, Y 1 is a single bond, Z 1 is -COO-,-(ring A 1 -Y 1 ) n 1 -ring B 1
-Z 1 - rings C 1 -, and n 2 is 1, Y 2 is a single bond, Z 2 is -COO- Roh - (Ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2
-For,
【化１１】 などが挙げられる。[Chemical 11] And the like.
【００３３】ｎ1が１、Ｙ1が単結合、Ｚ1が−ＯＣＯ−
の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および
ｎ2が１、Ｙ2が単結合、Ｚ2が−ＯＣＯ−の−（環Ａ2−
Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−としては、N 1 is 1, Y 1 is a single bond, and Z 1 is --OCO--.
Bruno - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 1, Y 2 is a single bond, Z 2 is -OCO- Roh - (Ring A 2 -
Y 2 ) n 2 -ring B 2 -Z 2 -ring C 2-
【化１２】 などが挙げられる。[Chemical 12] And the like.
【００３４】ｎ1が１、Ｙ1が−ＣＯＯ−、Ｚ1が単結合
の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および
ｎ2が１、Ｙ2が−ＣＯＯ−、Ｚ2が単結合の−（環Ａ2−
Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−としては、[0034] n 1 is 1, Y 1 is -COO-, Z 1 is a single bond - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 1 , Y 2 is —COO—, and Z 2 is a single bond — (ring A 2 —
Y 2 ) n 2 -ring B 2 -Z 2 -ring C 2-
【化１３】 などが挙げられる。[Chemical 13] And the like.
【００３５】ｎ1が１、Ｙ1が−ＯＣＯ−、Ｚ1が単結合
の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および
ｎ2が１、Ｙ2が−ＯＣＯ−、Ｚ2が単結合の−（環Ａ2−
Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−としては、N 1 is 1, Y 1 is -OCO-, Z 1 is a single bond of-(ring A 1 -Y 1 ) n 1 -ring B 1 -Z 1 -ring C 1- , and n 2 is 1. , Y 2 is —OCO—, and Z 2 is a single bond — (ring A 2 —
Y 2 ) n 2 -ring B 2 -Z 2 -ring C 2-
【化１４】 などが挙げられる。Embedded image And the like.
【００３６】ｎ1が１、Ｙ1が単結合、Ｚ1が−ＣＨ2Ｏ−
の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および
ｎ2が１、Ｙ2が単結合、Ｚ2が−ＣＨ2Ｏ−の−（環Ａ2
−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−としては、N 1 is 1, Y 1 is a single bond, and Z 1 is --CH 2 O--.
Bruno - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 1, Y 2 is a single bond, Z 2 is -CH 2 O-Bruno - (Ring A 2
-Y 2 ) n 2 -ring B 2 -Z 2 -ring C 2-
【化１５】 などが挙げられる。[Chemical 15] And the like.
【００３７】ｎ1が１、Ｙ1が単結合、Ｚ1が−ＯＣＨ2−
の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および
ｎ2が１、Ｙ2が単結合、Ｚ2が−ＯＣＨ2−の−（環Ａ2
−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−としては、N 1 is 1, Y 1 is a single bond, and Z 1 is --OCH 2-.
Bruno - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 1, Y 2 is a single bond, Z 2 is -OCH 2 - Bruno - (ring A 2
-Y 2 ) n 2 -ring B 2 -Z 2 -ring C 2-
【化１６】 などが挙げられる。Embedded image And the like.
【００３８】ｎ1が１、Ｙ1が−ＣＨ2Ｏ−、Ｚ1が単結合
の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および
ｎ2が１、Ｙ2が−ＣＨ2Ｏ−、Ｚ2が単結合の−（環Ａ2
−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−としては、[0038] n 1 is 1, Y 1 is -CH 2 O-, Z 1 is a single bond - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 Is 1, Y 2 is —CH 2 O—, and Z 2 is a single bond — (ring A 2
-Y 2 ) n 2 -ring B 2 -Z 2 -ring C 2-
【化１７】 などが挙げられる。[Chemical 17] And the like.
【００３９】ｎ1が１、Ｙ1が−ＯＣＨ2−、Ｚ1が単結合
の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、および
ｎ2が１、Ｙ2が−ＯＣＨ2−、Ｚ2が単結合の−（環Ａ2
−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−としては、[0039] n 1 is 1, Y 1 is -OCH 2 -, Z 1 is a single bond - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 1, Y 2 is —OCH 2 —, and Z 2 is a single bond — (ring A 2
-Y 2 ) n 2 -ring B 2 -Z 2 -ring C 2-
【化１８】 などが挙げられる。Embedded image And the like.
【００４０】ｎ1が１、Ｙ1およびＺ1が単結合の−（環
Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2が
１、Ｙ2およびＺ2が単結合の−（環Ａ2−Ｙ2）ｎ2−環
Ｂ2−Ｚ2−環Ｃ2−としては、[0040] n 1 is 1, Y 1 and Z 1 is a single bond - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 1, Y 2 and Z 2 is a single bond - (ring a 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as is
【化１９】 などが挙げられる。[Chemical 19] And the like.
【００４１】ｎ1が１、Ｙ1およびＺ1が−ＣＯＯ−の−
（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2
が１、Ｙ2およびＺ2が−ＣＯＯ−の−（環Ａ2−Ｙ2）ｎ
2−環Ｂ2−Ｚ2−環Ｃ2−としては、N 1 is 1, Y 1 and Z 1 are --COO--
(Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2
Is 1, and Y 2 and Z 2 are —COO— of — (ring A 2 —Y 2 ) n.
2 - Ring B 2 -Z 2 - ring C 2 - as is
【化２０】 などが挙げられる。Embedded image And the like.
【００４２】ｎ1が１、Ｙ1およびＺ1のいずれかが−Ｃ
≡Ｃ−の−（環Ａ1−Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、
およびｎ2が１、Ｙ2およびＺ2のいずれかが−Ｃ≡Ｃ−
の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−として
は、N 1 is 1, and one of Y 1 and Z 1 is -C.
≡C- Bruno - (Ring A 1 -Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -,
And n 2 is 1, and any one of Y 2 and Z 2 is -C≡C-
Bruno - (ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as is
【化２１】 などが挙げられる。[Chemical 21] And the like.
【００４３】ｎ1が０、Ｚ1が単結合の−（環Ａ1−Ｙ1）
ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2が０、Ｚ2が単結
合の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環Ｃ2−として
は、N 1 is 0 and Z 1 is a single bond of-(ring A 1 -Y 1 ).
n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 0, Z 2 is a single bond - (ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as,
【化２２】 などが挙げられる。[Chemical formula 22] And the like.
【００４４】ｎ1が０、Ｚ1が−ＣＯＯ−の−（環Ａ1−
Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2が０、Ｚ2
が−ＣＯＯ−の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環
Ｃ2−としては、N 1 is 0 and Z 1 is --COO--, and is-(ring A 1-).
Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 0, Z 2
There -COO- Bruno - (ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as is
【化２３】 などが挙げられる。[Chemical formula 23] And the like.
【００４５】ｎ1が０、Ｚ1が−ＯＣＯ−の−（環Ａ1−
Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2が０、Ｚ2
が−ＯＣＯ−の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環
Ｃ2−としては、[0045] n 1 is 0, Z 1 is -OCO- Bruno - (Ring A 1 -
Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 0, Z 2
There -OCO- Bruno - (ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as is
【化２４】 などが挙げられる。[Chemical formula 24] And the like.
【００４６】ｎ1が０、Ｚ1が−ＣＨ2Ｏ−の−（環Ａ1−
Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2が０、Ｚ2
が−ＣＨ2Ｏ−の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環
Ｃ2−としては、N 1 is 0 and Z 1 is --CH 2 O--, and is-(ring A 1-).
Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 0, Z 2
There -CH 2 O-Bruno - (ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as is
【化２５】 などが挙げられる。[Chemical 25] And the like.
【００４７】ｎ1が０、Ｚ1が−ＯＣＨ2−の−（環Ａ1−
Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2が０、Ｚ2
が−ＯＣＨ2−の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環
Ｃ2−としては、N 1 is 0 and Z 1 is -OCH 2- (ring A 1-
Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 0, Z 2
There -OCH 2 - Bruno - (ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as is
【化２６】 などが挙げられる。[Chemical formula 26] And the like.
【００４８】ｎ1が０、Ｚ1が−Ｃ≡Ｃ−の−（環Ａ1−
Ｙ1）ｎ1−環Ｂ1−Ｚ1−環Ｃ1−、およびｎ2が０、Ｚ2
が−Ｃ≡Ｃ−の−（環Ａ2−Ｙ2）ｎ2−環Ｂ2−Ｚ2−環
Ｃ2−としては、When n 1 is 0 and Z 1 is -C≡C-,-(ring A 1-
Y 1) n 1 - Ring B 1 -Z 1 - rings C 1 -, and n 2 is 0, Z 2
There -C≡C- Bruno - (ring A 2 -Y 2) n 2 - ring B 2 -Z 2 - ring C 2 - as is
【化２７】 などが挙げられる。[Chemical 27] And the like.
【００４９】本発明の化合物の具体例を以下に挙げるが
本発明はこれに限定されるものではない。Specific examples of the compound of the present invention are shown below, but the present invention is not limited thereto.
【００５０】[0050]
【表１】 化合物Ｎｏ． １ ２ ３ ４ ５ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 1 Compound No. 1 2 3 4 5 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same left Same left Same left Same left Same as left C 1 1,4-ph Same left Same left Same left Same left Same as left C 2 1,4-ph Same left Same left Same left Same left same m 7 Same left Same left Same left same left n 1 1 Same left same left Same left same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００５１】[0051]
【表２】 化合物Ｎｏ． ６ ７ ８ ９ １０ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 2 Compound No. 6 7 8 9 10 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００５２】[0052]
【表３】 化合物Ｎｏ． １１ １２ １３ １４ １５ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 3 Compound No. 11 12 13 14 15 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００５３】[0053]
【表４】 化合物Ｎｏ． １６ １７ １８ １９ ２０ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ８ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 4 Compound No. 16 17 18 19 20 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same as left Same as left Same as left Same as left C 1 1,4-ph Same as left Same left Same as left Same as left C 2 1,4-ph Same left Same left Same left Same left m 8 Same left Same left Same left Same left n 1 1 Same left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００５４】[0054]
【表５】 化合物Ｎｏ． ２１ ２２ ２３ ２４ ２５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ８ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 5 Compound No. 21 22 23 24 25 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 8 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００５５】[0055]
【表６】 化合物Ｎｏ． ２６ ２７ ２８ ２９ ３０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ８ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 6 Compound No. 26 27 28 29 30 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 8 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００５６】[0056]
【表７】 化合物Ｎｏ． ３１ ３２ ３３ ３４ ３５ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ９ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 7 Compound No. 31 32 33 34 34 35 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same left Same left Same left Same left Same ring C 1 1,4-ph Same left Same left Same left Same left Same ring C 2 1,4-ph Same left Same left Same left Same left m 9 Same left Same left Same left Same left n 1 1 Same left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００５７】[0057]
【表８】 化合物Ｎｏ． ３６ ３７ ３８ ３９ ４０ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ９ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 8 Compound No. 36 37 38 39 40 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 9 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００５８】[0058]
【表９】 化合物Ｎｏ． ４１ ４２ ４３ ４４ ４５ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ９ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 9 Compound No. 41 42 43 44 45 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 9 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００５９】[0059]
【表１０】 化合物Ｎｏ． ４６ ４７ ４８ ４９ ５０ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １０ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 10 Compound No. 46 47 48 49 50 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same left Same left Same left Same left Ring C 1 1,4-ph Same left Same left Same left Same left Ring C 2 1,4-ph Same left Same left Same left Same left m 10 Same left Same left Same left Same left n 1 1 Same left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００６０】[0060]
【表１１】 化合物Ｎｏ． ５１ ５２ ５３ ５４ ５５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １０ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 11 Compound No. 51 52 53 54 55 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 10 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００６１】[0061]
【表１２】 化合物Ｎｏ． ５６ ５７ ５８ ５９ ６０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １０ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 12 Compound No. 56 57 58 59 60 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 10 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００６２】[0062]
【表１３】 化合物Ｎｏ． ６１ ６２ ６３ ６４ ６５ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １１ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 13 Compound No. 61 62 63 64 65 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same left Same left Same left Same left Same ring C 1 1,4-ph Same left Same left Same left Same left Same ring C 2 1,4-ph Same left Same left Same left Same left Same m 1 Same left Same left Same left Same left n 1 1 Same left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００６３】[0063]
【表１４】 化合物Ｎｏ． ６６ ６７ ６８ ６９ ７０ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １１ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 14 Compound No. 66 67 68 68 70 70 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 11 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００６４】[0064]
【表１５】 化合物Ｎｏ． ７１ ７２ ７３ ７４ ７５ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １１ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 15 Compound No. 71 72 73 74 75 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 11 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００６５】[0065]
【表１６】 化合物Ｎｏ． ７６ ７７ ７８ ７９ ８０ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １２ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 16 Compound No. 76 77 78 78 79 80 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same left Same left Same left Same left Same ring Left C 1 1,4-ph Same left Same left Same left Same left Same ring Same as left C 2 1,4-ph Same left Same left Same left Same left m 12 Same left Same left Same left Same left n 1 1 Same left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００６６】[0066]
【表１７】 化合物Ｎｏ． ８１ ８２ ８３ ８４ ８５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １２ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 17 Compound No. 81 82 83 84 85 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 12 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００６７】[0067]
【表１８】 化合物Ｎｏ． ８６ ８７ ８８ ８９ ９０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １２ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 18 Compound No. 86 87 88 89 90 90 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 12 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００６８】[0068]
【表１９】 化合物Ｎｏ． ９１ ９２ ９３ ９４ ９５ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １３ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 19 Compound No. 91 92 93 94 95 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same left Same left Same left Same left Ring C 1 1,4-ph Same left Same left Same left Same left Same ring C 2 1,4-ph Same left Same left Same left Same left Same m 13 Same left Same left Same left Same left n 1 1 Same left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００６９】[0069]
【表２０】 化合物Ｎｏ． ９６ ９７ ９８ ９９ １００ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １３ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 20 Compound No. 96 97 98 99 100 100 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same as left C 1 1,4-ph Same left Same left Same left Same left same left C 2 1,4-ph Same left Same left Same left Same left Same left same left Same left Same left n 1 1 Same left same left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００７０】[0070]
【表２１】 化合物Ｎｏ． １０１ １０２ １０３ １０４ １０５ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １３ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 21 Compound No. 101 102 103 104 105 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same as left C 1 1,4-ph Same left Same left Same left Same left same left C 2 1,4-ph Same left Same left Same left Same left Same left same left Same left Same left n 1 1 Same left same left indicates Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group .
【００７１】[0071]
【表２２】 化合物Ｎｏ． １０６ １０７ １０８ １０９ １１０ Ｒ1 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 ＣＨ3 Ｃ2Ｈ5 Ｃ3Ｈ7 Ｃ4Ｈ9 Ｃ5Ｈ11 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １４ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 22 Compound No. 106 107 108 108 109 110 R 1 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 CH 3 C 2 H 5 C 3 H 7 C 4 H 9 C 5 H 11 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same left Same left Same left Same left Same as left C 1 1,4-ph Same left Same left Same left Same left Same as left C 2 1,4-ph Same left Same left Same left Same left m 14 Same left Same left Same left same left n 1 1 Same left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【００７２】[0072]
【表２３】 化合物Ｎｏ． １１１ １１２ １１３ １１４ １１５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １４ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 23 Compound No. 111 112 113 113 114 115 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 14 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【００７３】[0073]
【表２４】 化合物Ｎｏ． １１６ １１７ １１８ １１９ １２０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １４ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 24 Compound No. 116 117 118 118 119 120 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 14 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left indicates Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group .
【００７４】[0074]
【表２５】 化合物Ｎｏ． １２１ １２２ １２３ １２４ １２５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 25 Compound No. 121 122 123 123 124 125 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left Same left same left same left m 7 Same left same left same left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group .
【００７５】[0075]
【表２６】 化合物Ｎｏ． １２６ １２７ １２８ １２９ １３０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 26 Compound No. 126 127 128 128 129 130 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left Same left same left same left m 7 Same left same left same left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group Show.
【００７６】[0076]
【表２７】 化合物Ｎｏ． １３１ １３２ １３３ １３４ １３５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ８ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 27 Compound No. 131 132 133 133 134 135 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same left ring C 2 1,4-ph Same left same left Same left same left same left m 8 Same left same left same left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group .
【００７７】[0077]
【表２８】 化合物Ｎｏ． １３６ １３７ １３８ １３９ １４０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ８ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 28 Compound No. 136 137 138 139 140 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same left ring C 2 1,4-ph Same left same left Same left same left same left m 8 Same left same left same left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group Show.
【００７８】[0078]
【表２９】 化合物Ｎｏ． １４１ １４２ １４３ １４４ １４５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ９ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 29 Compound No. 141 142 143 144 145 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left Same left same left same left m 9 Same left same left same left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group .
【００７９】[0079]
【表３０】 化合物Ｎｏ． １４６ １４７ １４８ １４９ １５０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ９ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 30 Compound No. 146 147 148 149 150 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left Same left same left same left m 9 Same left same left same left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group Show.
【００８０】[0080]
【表３１】 化合物Ｎｏ． １５１ １５２ １５３ １５４ １５５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １０ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 31 Compound No. 151 152 153 154 155 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left same left same left m 10 Same left same left same left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group You
【００８１】[0081]
【表３２】 化合物Ｎｏ． １５６ １５７ １５８ １５９ １６０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １０ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 32 Compound No. 156 157 158 159 160 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left same left same left m 10 Same left same left same left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is 1,4-phenylene It is shown.
【００８２】[0082]
【表３３】 化合物Ｎｏ． １６１ １６２ １６３ １６４ １６５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １１ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 33 Compound No. 161 162 163 164 165 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left Same left same left m 11 Same left same left Same left same left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group You
【００８３】[0083]
【表３４】 化合物Ｎｏ． １６６ １６７ １６８ １６９ １７０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １１ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 34 Compound No. 166 167 168 169 170 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 1,4-ph Same left same left Same left same left m 11 Same left same left Same left same left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is 1,4-phenylene It is shown.
【００８４】[0084]
【表３５】 化合物Ｎｏ． １７１ １７２ １７３ １７４ １７５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 35 Compound No. 171 172 173 174 175 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left indicates Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group .
【００８５】[0085]
【表３６】 化合物Ｎｏ． １７６ １７７ １７８ １７９ １８０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 36 Compound No. 176 177 178 179 180 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is 1,4-phenylene It is shown.
【００８６】[0086]
【表３７】 化合物Ｎｏ． １８１ １８２ １８３ １８４ １８５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ８ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 37 Compound No. 181 182 183 184 185 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 8 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left indicates Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group .
【００８７】[0087]
【表３８】 化合物Ｎｏ． １８６ １８７ １８８ １８９ １９０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ８ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 38 Compound No. 186 187 188 189 190 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 8 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is 1,4-phenylene It is shown.
【００８８】[0088]
【表３９】 化合物Ｎｏ． １９１ １９２ １９３ １９４ １９５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ９ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 39 Compound No. 191 192 193 194 195 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 9 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left indicates Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group .
【００８９】[0089]
【表４０】 化合物Ｎｏ． １９６ １９７ １９８ １９９ ２００ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ９ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 40 Compound No. 196 197 198 199 200 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 9 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is 1,4-phenylene It is shown.
【００９０】[0090]
【表４１】 化合物Ｎｏ． ２０１ ２０２ ２０３ ２０４ ２０５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １０ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 41 Compound No. 201 202 203 204 205 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 10 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left the Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group It is.
【００９１】[0091]
【表４２】 化合物Ｎｏ． ２０６ ２０７ ２０８ ２０９ ２１０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １０ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 42 Compound No. 206 207 208 208 209 210 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 10 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-phenylene A group.
【００９２】[0092]
【表４３】 化合物Ｎｏ． ２１１ ２１２ ２１３ ２１４ ２１５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １１ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 43 Compound No. 211 212 213 214 215 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 11 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left the Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group It is.
【００９３】[0093]
【表４４】 化合物Ｎｏ． ２１６ ２１７ ２１８ ２１９ ２２０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １１ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 44 Compound No. 216 217 218 219 220 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 11 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-phenylene A group.
【００９４】[0094]
【表４５】 化合物Ｎｏ． ２２１ ２２２ ２２３ ２２４ ２２５ Ｒ1 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ6Ｈ13 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １２ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 45 Compound No. 221 222 223 224 225 R 1 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 6 H 13 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 12 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left the Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group It is.
【００９５】[0095]
【表４６】 化合物Ｎｏ． ２２６ ２２７ ２２８ ２２９ ２３０ Ｒ1 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ11Ｈ23 Ｃ12Ｈ25 Ｃ13Ｈ27 Ｃ14Ｈ29 Ｃ15Ｈ31 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 同左 同左 Ｘ2 ＣＯＯ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ １２ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。Table 46 Compound No. 226 227 228 229 230 R 1 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 11 H 23 C 12 H 25 C 13 H 27 C 14 H 29 C 15 H 31 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 COO Same as at left Same as at left Same as at left Same as at left X 2 COO Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 12 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-phenylene A group.
【００９６】[0096]
【表４７】 化合物Ｎｏ． ２３１ ２３２ ２３３ ２３４ ２３５ Ｒ1 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 単結合 同左 Ｘ2 Ｏ 同左 同左 単結合 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 3-フルオロ-＊2 1,4-ph 1,4-ph 3-フルオロ- 環Ａ2 1,4-ph 3-フルオロ- 1,4-ph 1,4-ph 3-フルオロ- 環Ｂ1 3-フルオロ- 1,4-ph 1,4-ph 3-フルオロ- 1,4-ph 環Ｂ2 3-フルオロ- 1,4-ph 1,4-ph 3-フルオロ- 1,4-ph 環Ｃ1 1,4-ph 1,4-ph 3-フルオロ- 1,4-ph 1,4-ph 環Ｃ2 1,4-ph 1,4-ph 3-フルオロ- 1,4-ph 1,4-ph ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊23-フルオロ-は下記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 47 Compound No. 231 232 233 234 235 R 1 C 8 H 17 C 8 H 17 C 8 H 17 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 9 H 19 C 9 H 19 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same as left Same left Same bond Same left X 2 O Same left Same left Same bond Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 3- fluoro - * 2 1,4-ph 1,4- ph 3- fluoro - ring A 2 1,4-ph 3-fluoro-1,4-ph 1,4-ph 3-fluoro-ring B 1 3-fluoro-1,4-ph 1,4-ph 3-fluoro-1,4-ph ring B 2 3-Fluoro-1,4-ph 1,4-ph 3-Fluoro-1,4-ph ring C 1 1,4-ph 1,4-ph 3-Fluoro-1,4-ph 1,4 -ph ring C 2 1,4-ph 1,4-ph 3- fluoro - 1,4-ph 1,4-ph m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left 2 1 Same as at left Same as at left Same as at left Same as at left * 1 l, 4-ph represents a 1,4-phenylene group. * 2 3-Fluoro- represents a 3-fluoro-1,4-phenylene group of the following formula (A).
【化２８】 [Chemical 28]
【００９７】[0097]
【表４８】 化合物Ｎｏ． ２３６ ２３７ ２３８ ２３９ ２４０ Ｒ1 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 ＣＯＯ 同左 同左 ＯＣＯ Ｘ2 単結合 ＣＯＯ 同左 同左 ＯＣＯ Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 3-フルオロ-＊2 1,4-ph 1,4-ph 3-フルオロ- 環Ａ2 1,4-ph 3-フルオロ- 1,4-ph 1,4-ph 3-フルオロ- 環Ｂ1 1,4-ph 1,4-ph 1,4-ph 3-フルオロ- 1,4-ph 環Ｂ2 1,4-ph 1,4-ph 1,4-ph 3-フルオロ- 1,4-ph 環Ｃ1 3-フルオロ- 1,4-ph 3-フルオロ- 1,4-ph 1,4-ph 環Ｃ2 3-フルオロ- 1,4-ph 3-フルオロ- 1,4-ph 1,4-ph ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊23-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 48 Compound No. 236 237 238 239 240 R 1 C 9 H 19 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 9 H 19 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 Single bond COO Same as left Same as left OCO X 2 Single bond COO Same as left Same as left OCO Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 3- fluoro - * 2 1,4-ph 1,4- ph 3- fluoro - ring A 2 1,4-ph 3-fluoro- 1,4-ph 1,4-ph 3-fluoro-ring B 1 1,4-ph 1,4-ph 1,4-ph 3-fluoro- 1,4-ph Ring B 2 1,4-ph 1,4-ph 1,4-ph 3-Fluoro-1,4-ph Ring C 1 3-Fluoro-1,4-ph 3-Fluoro-1,4-ph 1, 4-ph ring C 2 3-Fluoro-1,4-ph 3-Fluoro-1,4-ph 1,4-ph m 7 Same as left Same as left Same as left Same as left n 1 1 Same as left Same as left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【００９８】[0098]
【表４９】 化合物Ｎｏ． ２４１ ２４２ ２４３ ２４４ ２４５ Ｒ1 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 ＯＣＯ 同左 Ｏ 同左 同左 Ｘ2 ＯＣＯ 同左 Ｏ 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 3-フルオロ-＊2 1,4-ph 1,4-ph 1,4-シクロ＊3 環Ａ2 1,4-ph 3-フルオロ- 1,4-ph 1,4-ph 1,4-シクロ 環Ｂ1 1,4-ph 1,4-ph 1,4-ph 1,4-シクロ 1,4-ph 環Ｂ2 1,4-ph 1,4-ph 1,4-ph 1,4-シクロ 1,4-ph 環Ｃ1 3-フルオロ- 1,4-ph 1,4-シクロ 1,4-ph 1,4-ph 環Ｃ2 3-フルオロ- 1,4-ph 1,4-シクロ 1,4-ph 1,4-ph ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊23-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊31,4-シクロは１，４−シクロヘキシレン基を示す。Table 49 Compound No. 241 242 243 244 245 R 1 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 OCO Same left O Same left Same left X 2 OCO Same left O Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Same as Z 2 COO Same as left Same as left Same as left Same as left Ring A 1 1,4-ph * 1 3-Fluoro- * 2 1,4-ph 1,4-ph 1,4-cyclo * 3 Ring A 2 1,4-ph 3-fluoro-1,4-ph 1,4-ph 1,4-cyclo ring B 1 1,4-ph 1,4-ph 1,4-ph 1,4-cyclo 1, 4-ph ring B 2 1,4-ph 1,4-ph 1,4-ph 1,4-cyclo 1,4-ph ring C 1 3-fluoro-1,4-ph 1,4-cyclo 1, 4-ph 1,4-ph ring C 2 3-fluoro-1,4-ph 1,4-cyclo 1,4-ph 1,4-ph m 7 Same as left Same as left Same as same left n 1 1 Same as left Same left Same left Same left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【００９９】[0099]
【表５０】 化合物Ｎｏ． ２４６ ２４７ ２４８ ２４９ ２５０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 ＣＯＯ ＣＯＯ Ｘ2 単結合 同左 同左 ＣＯＯ ＣＯＯ Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 1,4-シクロ＊3 1,4-ph 1,4-ph 1,4-シクロ 環Ａ2 1,4-ph 1,4-シクロ 1,4-ph 1,4-ph 1,4-シクロ 環Ｂ1 1,4-シクロ 1,4-ph 1,4-ph 1,4-シクロ 1,4-ph 環Ｂ2 1,4-シクロ 1,4-ph 1,4-ph 1,4-シクロ 1,4-ph 環Ｃ1 1,4-ph 1,4-ph 1,4-シクロ 1,4-ph 1,4-ph 環Ｃ2 1,4-ph 1,4-ph 1,4-シクロ 1,4-ph 1,4-ph ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊31,4-シクロは１，４−シクロヘキシレン基を示す。Table 50 Compound No. 246 247 248 249 250 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 Single bond Same as left Same as left COO COO X 2 Single bond Same as left Same as left COO COO Y 1 Single bond Same as left Same left Same left Same left Y 2 Single bond Same left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 1,4- cyclo * 3 1,4-ph 1,4-ph 1,4- cyclic ring A 2 1,4-ph 1,4-cyclo 1,4-ph 1,4-ph 1,4-cyclo ring B 1 1,4-cyclo 1,4-ph 1,4-ph 1,4-cyclo 1,4-ph ring B 2 1,4-cyclo 1,4-ph 1,4-ph 1,4-cyclo 1,4-ph ring C 1 1,4-ph 1,4-ph 1,4- Cyclo 1,4-ph 1,4-ph Ring C 2 1,4-ph 1,4-ph 1,4-Cyclo 1,4-ph 1,4-ph m 7 Same as left Same as left Same as left Same as left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１００】[0100]
【表５１】 化合物Ｎｏ． ２５１ ２５２ ２５３ ２５４ Ｒ1 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 Ｘ1 ＣＯＯ ＯＣＯ 同左 同左 Ｘ2 ＣＯＯ ＯＣＯ 同左 同左 Ｙ1 単結合 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 環Ａ1 1,4-ph＊1 1,4-シクロ＊3 1,4-ph 1,4-ph 環Ａ2 1,4-ph 1,4-シクロ 1,4-ph 1,4-ph 環Ｂ1 1,4-ph 1,4-ph 1,4-ph 1,4-シクロ 環Ｂ2 1,4-ph 1,4-ph 1,4-ph 1,4-シクロ 環Ｃ1 1,4-シクロ 1,4-ph 1,4-シクロ 1,4-ph 環Ｃ2 1,4-シクロ 1,4-ph 1,4-シクロ 1,4-ph ｍ ７ 同左 同左 同左 ｎ1 １ 同左 同左 同左 ｎ2 １ 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊31,4-シクロは１，４−シクロヘキシレン基を示す。Table 51 Compound No. 251 252 253 254 R 1 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left X 1 COO OCO Same as left Same left X 2 COO OCO Same as left Same left Y 1 Single bond Same left Same left Same left Y 2 Single bond Same left Same left Same left Same left Z 1 COO Same left Same left Same left Z 2 COO Same left Same left Same left ring A 1 1,4-ph * 1 1,4-cyclo * 3 1,4-ph 1,4-ph ring A 2 1,4-ph 1,4-cyclo 1,4-ph 1,4-ph ring B 1 1,4-ph 1,4-ph 1,4-ph 1,4-cyclo ring B 2 1,4-ph 1,4-ph 1,4-ph 1,4-cyclo ring C 1 1,4 -Cyclo 1,4-ph 1,4-cyclo 1,4-ph ring C 2 1,4-cyclo 1,4-ph 1,4-cyclo 1,4-ph m 7 Same as left Same as left Same as left n 1 1 Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１０１】[0101]
【表５２】 化合物Ｎｏ． ２５５ ２５６ ２５７ ２５８ ２５９ Ｒ1 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 単結合 単結合 Ｘ2 Ｏ 同左 同左 単結合 単結合 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 2,6-ナフチ＊4 1,4-ph 1,4-ph 2,6-ナフチ 環Ａ2 1,4-ph 2,6-ナフチ 1,4-ph 1,4-ph 2,6-ナフチ 環Ｂ1 2,6-ナフチ 1,4-ph 1,4-ph 2,6-ナフチ 1,4-ph 環Ｂ2 2,6-ナフチ 1,4-ph 1,4-ph 2,6-ナフチ 1,4-ph 環Ｃ1 1,4-ph 1,4-ph 2,6-ナフチ 1,4-ph 1,4-ph 環Ｃ2 1,4-ph 1,4-ph 2,6-ナフチ 1,4-ph 1,4-ph ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊42,6-ナフチは２，６−ナフチレン基を示す。Table 52 Compound No. 255 256 257 258 259 R 1 C 8 H 17 C 8 H 17 C 8 H 17 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 9 H 19 C 9 H 19 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same as left Same as left Single bond Single bond X 2 O Same as left Same left Same bond Single bond Y 1 single bond Same left Same left Same left Y 2 single binding Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 2,6- naphth * 4 1,4-ph 1,4-ph 2,6- Naphthyl ring A 2 1,4-ph 2,6-naphthyl 1,4-ph 1,4-ph 2,6-naphthyl ring B 1 2,6-naphthyl 1,4-ph 1,4-ph 2,6 -Naphthi 1,4-ph ring B 2 2,6-naphthy 1,4-ph 1,4-ph 2,6-naphthy 1,4-ph ring C 1 1,4-ph 1,4-ph 2, 6-naphthi 1,4-ph 1,4-ph ring C 2 1,4-ph 1,4-ph 2,6-naphthy 1,4-ph 1,4-ph m 7 Same as left Same as left Same as left Same as left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１０２】[0102]
【表５３】 化合物Ｎｏ． ２６０ ２６１ ２６２ ２６３ ２６４ Ｒ1 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 ＣＯＯ 同左 同左 ＯＣＯ Ｘ2 単結合 ＣＯＯ 同左 同左 ＯＣＯ Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 2,6-ナフチ＊4 1,4-ph 1,4-ph 2,6-ナフチ 環Ａ2 1,4-ph 2,6-ナフチ 1,4-ph 1,4-ph 2,6-ナフチ 環Ｂ1 1,4-ph 1,4-ph 1,4-ph 2,6-ナフチ 1,4-ph 環Ｂ2 1,4-ph 1,4-ph 1,4-ph 2,6-ナフチ 1,4-ph 環Ｃ1 2,6-ナフチ 1,4-ph 2,6-ナフチ 1,4-ph 1,4-ph 環Ｃ2 2,6-ナフチ 1,4-ph 2,6-ナフチ 1,4-ph 1,4-ph ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊42,6-ナフチは２，６−ナフチレン基を示す。Table 53 Compound No. 260 261 262 263 264 R 1 C 9 H 19 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 9 H 19 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 Single bond COO Same as left Same as left OCO X 2 Single bond COO Same as left Same as left OCO Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same as left Same as left Same as left Z 1 COO Same as left Same left Same as left Same left Z 2 COO Same as left Same left Same left Same left Ring A 1 1,4-ph * 1 2,6-Naphti * 4 1,4-ph 1,4-ph 2,6-Naphti Ring A 2 1,4-ph 2,6-naphthy 1,4-ph 1,4-ph 2,6-naphthy ring B 1 1,4-ph 1,4-ph 1,4-ph 2,6-naphthy l, 4-ph ring B 2 1,4-ph 1,4-ph 1,4-ph 2,6- naphth l, 4-ph ring C 1 2,6 naphth l, 4-ph 2,6 Naphth 1,4-ph 1,4-ph Ring C 2 2,6-Naphth 1,4-ph 2,6-Naphth 1,4-ph 1,4-ph m 7 Same as left Same as left Same as left Same as left n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１０３】[0103]
【表５４】 化合物Ｎｏ． ２６５ ２６６ ２６７ ２６８ Ｒ1 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 Ｘ1 ＯＣＯ 同左 Ｏ 同左 Ｘ2 ＯＣＯ 同左 Ｏ 同左 Ｙ1 単結合 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 環Ａ1 1,4-ph＊1 1,4-ph 1,4-ph 1,4-ph 環Ａ2 1,4-ph 1,4-ph 1,4-ph 1,4-ph 環Ｂ1 1,4-ph 2,6-ナフチ＊4 1,4-ph ヒ゜リミシ゛ン＊5 環Ｂ2 1,4-ph 2,6-ナフチ 1,4-ph ヒ゜リミシ゛ン 環Ｃ1 2,6-ナフチ 1,4-ph ヒ゜リミシ゛ン 1,4-ph 環Ｃ2 2,6-ナフチ 1,4-ph ヒ゜リミシ゛ン 1,4-ph ｍ ７ 同左 同左 同左 ｎ1 １ 同左 同左 同左 ｎ2 １ 同左 同左 同左 ＊11,4-phは１，４−フェニレン基を示す。 ＊42,6-ナフチは２，６−ナフチレン基 を示す。 ＊5ヒ゜リミシ゛ンは下記式（Ｂ）のピリミジン−２，５−ジイル基を示す。 Table 54 Compound No. 265 266 267 268 R 1 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left X 1 OCO Same as left O Same as left X 2 OCO Same as left O Same as left Y 1 Single bond Same as left Same as left Same as left Y 2 Single bond Same left Same left Same left Same left Z 1 COO Same left Same left Same left Z 2 COO Same left Same left Same ring A 1 1,4-ph * 1 1,4-ph 1,4-ph 1,4-ph ring A 2 1,4-ph 1,4-ph 1,4-ph 1,4-ph ring B 1 1 , 4-ph 2,6-naphthi * 4 1,4-ph polyimidin * 5 ring B 2 1,4-ph 2,6-naphthi 1,4-ph polyimidin ring C 1 2,6-naphthi 1,4- ph Premium 1,4-ph Ring C 2 2,6-Naphth 1,4-ph Premium 1,4-ph m 7 Same as left Same as left Same as left n 1 1 Same as left Same left Same as left n 2 1 Same left Same left Same left * 1 1,4-ph Represents a 1,4-phenylene group. * 4 2,6-naphthyl means 2,6-naphthylene group. * 5 Polyimidine represents a pyrimidine-2,5-diyl group represented by the following formula (B).
【化２９】 [Chemical 29]
【０１０４】[0104]
【表５５】 化合物Ｎｏ． ２６９ ２７０ ２７１ ２７２ Ｒ1 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 Ｘ1 Ｏ 単結合 同左 同左 Ｘ2 Ｏ 単結合 同左 同左 Ｙ1 単結合 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 環Ａ1 ヒ゜リミシ゛ン＊5-1 ヒ゜リミシ゛ン＊5-1 1,4-ph＊1 1,4-ph 環Ａ2 ヒ゜リミシ゛ン＊5-1 ヒ゜リミシ゛ン＊5-1 1,4-ph 1,4-ph 環Ｂ1 1,4-ph 1,4-ph 1,4-ph ヒ゜リミシ゛ン＊5 環Ｂ2 1,4-ph 1,4-ph 1,4-ph ヒ゜リミシ゛ン＊5 環Ｃ1 1,4-ph 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph 環Ｃ2 1,4-ph 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph ｍ ７ 同左 同左 同左 ｎ1 １ 同左 同左 同左 ｎ2 １ 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊5 ヒ゜リミシ゛ンは前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。 ＊5-1 ピリミジンは下記式（Ｃ）のピリミジン−２，５−ジイル基を示す。Table 55 Compound No. 269 270 271 272 R 1 C 8 H 17 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left R 3 C 8 H 17 C 9 H 19 C 9 H 19 C 9 H 19 R 4 CF 3 or CH 3 Same as left Same as left Same as left X 1 O Single bond Same as left Same as left X 2 O Single bond Same as left Same left Y 1 Single bond Same as left Same left Same left Y 2 Single bond Same left Same left Same left Same left Z 1 COO Same left Same left Same left Z 2 COO Same left Same left Same left Ring A 1 Premium * 5-1 Premium * 5-1 1,4-ph * 1 1,4-ph Ring A 2 Premium * 5-1 Premium * 5-1 1,4-ph 1,4-ph Ring B 1 1,4-ph 1,4-ph 1,4-ph polyimidin * 5 ring B 2 1,4-ph 1,4-ph 1,4-ph polyimidin * 5 ring C 1 1,4-ph 1, 4-ph premium * 5 1,4-ph ring C 2 1,4-ph 1,4-ph premium * 5 1,4-ph m 7 Same as left Same as left Same as left n 1 1 Same as left Same left same left n 2 1 Same left same left Same left * 1 l, 4-ph is shown a 1,4-phenylene group . * 5 Priminin represents the pyrimidine-2,5-diyl group of the above formula (B). * 5-1 Pyrimidine represents a pyrimidine-2,5-diyl group represented by the following formula (C).
【化３０】 Embedded image
【０１０５】[0105]
【表５６】 化合物Ｎｏ． ２７３ ２７４ ２７５ ２７６ Ｒ1 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 Ｘ1 ＣＯＯ 同左 同左 ＯＣＯ Ｘ2 ＣＯＯ 同左 同左 ＯＣＯ Ｙ1 単結合 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 環Ａ1 ヒ゜リミシ゛ン＊5-1 1,4-ph＊1 1,4-ph ヒ゜リミシ゛ン＊5-1 環Ａ2 ヒ゜リミシ゛ン＊5-1 1,4-ph 1,4-ph ヒ゜リミシ゛ン＊5-1 環Ｂ1 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph 1,4-ph 環Ｂ2 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph 1,4-ph 環Ｃ1 1,4-ph 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph 環Ｃ2 1,4-ph 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph ｍ ７ 同左 同左 同左 ｎ1 １ 同左 同左 同左 ｎ2 １ 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊5 ヒ゜リミシ゛ンは前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。 ＊5-1 ヒ゜リミシ゛ンは前記式（Ｃ）のピリミジン−２，５−ジイル基を示す。Table 56 Compound No. 273 274 275 276 R 1 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left X 1 COO Same as left Same as left OCO X 2 COO Same as left Same as left OCO Y 1 Single bond Same left Same left Same left Y 2 Single bond Same left Same left Same left Same left Z 1 COO Same left Same left Same left Z 2 COO Same left Same left Same left ring A 1 Premium * 5-1 1,4-ph * 1 1,4-ph Premium * 5-1 Ring A 2 Premium * 5-1 1,4-ph 1,4-ph Premium * 5-1 Ring B 1 1 , 4-ph polyimidin * 5 1,4-ph 1,4-ph ring B 2 1,4-ph polyimidin * 5 1,4-ph 1,4-ph ring C 1 1,4-ph 1,4- ph Premium * 5 1,4-ph Ring C 2 1,4-ph 1,4-ph Premium * 5 1,4-ph m 7 Same as left Same as left Same as left n 1 1 Same as left Same as same left n 2 1 Same as left Same as left * 1 1 , 4-ph is 1,4-phenyl Shows the emissions group. * 5 Priminin represents the pyrimidine-2,5-diyl group of the above formula (B). * 5-1 Primimin represents the pyrimidine-2,5-diyl group of the above formula (C).
【０１０６】[0106]
【表５７】 化合物Ｎｏ． ２７７ ２７８ ２７９ ２８０ Ｒ1 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 Ｘ1 ＯＣＯ 同左 Ｏ 同左 Ｘ2 ＯＣＯ 同左 Ｏ 同左 Ｙ1 単結合 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 環Ａ1 ヒ゜リミシ゛ン＊5-1 1,4-ph＊1 1,4-ph 5-フェニルヒ゜リ＊6 環Ａ2 ヒ゜リミシ゛ン＊5-1 1,4-ph 1,4-ph 5-フェニルヒ゜リ 環Ｂ1 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph 1,4-ph 環Ｂ2 1,4-ph ヒ゜リミシ゛ン＊5 1,4-ph 1,4-ph 環Ｃ1 1,4-ph 1,4-ph 5-フェニルヒ゜リ 1,4-ph 環Ｃ2 1,4-ph 1,4-ph 5-フェニルヒ゜リ 1,4-ph ｍ ７ 同左 同左 同左 ｎ1 １ 同左 同左 同左 ｎ2 １ 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊5 ヒ゜リミシ゛ンは前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。 ＊6 5-フェニルヒ゜リは下記式（Ｄ）の２−フェニルピリミジン−５−イル基を示す。 ＊5-1 ヒ゜リミシ゛ンは前記式（Ｃ）のピリミジン−２，５−ジイル基を示す。Table 57 Compound No. 277 278 279 280 R 1 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left X 1 OCO Same left O Same left X 2 OCO Same left O Same left Y 1 Single bond Same left Same left same left Y 2 Single bond Same left Same left Same left Same left Z 1 COO Same left Same left Same left Z 2 COO Same left Same left Same left Ring A 1 Polyimide * 5-1 1,4-ph * 1 1,4-ph 5-Phenylphenyl * 6 ring A 2 Polyimide * 5-1 1,4-ph 1,4-ph 5-Phenylphenyl ring B 1 1,4 -ph Polyimidin * 5 1,4-ph 1,4-ph Ring B 2 1,4-ph Polyimidin * 5 1,4-ph 1,4-ph Ring C 1 1,4-ph 1,4-ph 5 -Phenylphenyl 1,4-ph Ring C 2 1,4-ph 1,4-ph 5-Phenylphenyl 1,4-ph m 7 Same as left Same as left Same as left n 1 1 Same as left Same as left Same as left n 2 1 Same as left Same as left * 1 1,4 -ph represents a 1,4-phenylene group. * 5 Priminin represents the pyrimidine-2,5-diyl group of the above formula (B). * 6 5-Phenylphenyl represents a 2-phenylpyrimidin-5-yl group represented by the following formula (D). * 5-1 Primimin represents the pyrimidine-2,5-diyl group of the above formula (C).
【化３１】 [Chemical 31]
【０１０７】[0107]
【表５８】 化合物Ｎｏ． ２８１ ２８２ ２８３ ２８４ Ｒ1 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 Ｘ1 Ｏ 単結合 同左 同左 Ｘ2 Ｏ 単結合 同左 同左 Ｙ1 単結合 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 環Ａ1 5-フェニルヒ゜リ＊6 1,4-ph＊1 1,4-ph 5-フェニルヒ゜リ 環Ａ2 5-フェニルヒ゜リ 1,4-ph 1,4-ph 5-フェニルヒ゜リ 環Ｂ1 1,4-ph 5-フェニルヒ゜リ 1,4-ph 1,4-ph 環Ｂ2 1,4-ph 5-フェニルヒ゜リ 1,4-ph 1,4-ph 環Ｃ1 1,4-ph 1,4-ph 5-フェニルヒ゜リ 1,4-ph 環Ｃ2 1,4-ph 1,4-ph 5-フェニルヒ゜リ 1,4-ph ｍ ７ 同左 同左 同左 ｎ1 １ 同左 同左 同左 ｎ2 １ 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊6 5-フェニルヒ゜リは前記式（Ｄ）の２−フェニルピリミジン−５−イル基を示す。Table 58 Compound No. 281 282 283 284 R 1 C 8 H 17 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left R 3 C 8 H 17 C 9 H 19 C 9 H 19 C 9 H 19 R 4 CF 3 or CH 3 Same as left Same as left Same as left X 1 O Single bond Same as left Same as left X 2 O Single bond Same as left Same left Y 1 Single bond Same as left Same left Same left Y 2 Single bond Same left Same left Same left Same left Z 1 COO Same left Same left Same left Z 2 COO Same left Same left Same left Ring A 1 5-Phenyl Pull * 6 1,4-ph * 1 1,4-ph 5-Phenyl Pull Ring A 2 5-Phenyl Pull 1,4-ph 1,4-ph 5-Phenyl Pull Ring B 1 1,4-ph 5-phenyl pull 1,4-ph 1,4-ph ring B 2 1,4-ph 5-phenyl pull 1,4-ph 1,4-ph ring C 1 1,4-ph 1,4-ph 5-phenyl pull 1,4-ph Ring C 2 1,4-ph 1,4-ph 5-phenyl poly 1,4-ph m 7 Same as left Same as left Same as left n 1 1 Same as left Same as left Same n 2 1 Same as left Same left Same as left * 1 1,4-ph Represents a 1,4-phenylene group. * 6 5-Phenylphenyl represents the 2-phenylpyrimidin-5-yl group of the above formula (D).
【０１０８】[0108]
【表５９】 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊6 5-フェニルヒ゜リは前記式（Ｄ）の２−フェニルピリミジ
ン−５−イル基を示す。[Table 59] * 1 1,4-ph represents a 1,4-phenylene group. * 6 5-Phenylphenyl represents the 2-phenylpyrimidin-5-yl group of the above formula (D).
【０１０９】[0109]
【表６０】 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊6 5-フェニルヒ゜リは前記式（Ｄ）の２−フェニルピリミジ
ン−５−イル基を示す。[Table 60] * 1 1,4-ph represents a 1,4-phenylene group. * 6 5-Phenylphenyl represents the 2-phenylpyrimidin-5-yl group of the above formula (D).
【０１１０】[0110]
【表６１】 化合物Ｎｏ． ２９１ ２９２ ２９３ ２９４ ２９５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 61 Compound No. 291 292 293 294 295 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same left Same as left Same Z 2 COO Same left Same as left Same left Same as left Ring A 1 3-Fluoro- * 2 Same left Same left Same left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 8 9 9 10 11 n 1 1 Same left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１１１】[0111]
【表６２】 化合物Ｎｏ． ２９６ ２９７ ２９８ ２９９ ３００ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 62 Compound No. 296 297 298 299 300 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same left Same as left Same Z 2 COO Same left Same as left Same left Same as left Ring A 1 3-Fluoro- * 2 Same left Same left Same left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１１２】[0112]
【表６３】 化合物Ｎｏ． ３０１ ３０２ ３０３ ３０４ ３０５ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 63 Compound No. 301 302 302 303 304 305 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same left Same as left Same Z 2 COO Same left Same as left Same left Same as left Ring A 1 3-Fluoro- * 2 Same left Same left Same left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１１３】[0113]
【表６４】 化合物Ｎｏ． ３０６ ３０７ ３０８ ３０９ ３１０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 64 Compound No. 306 307 308 309 310 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same left Same left Same left Same left Same left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same ring C 1 3-Fluoro- * 2 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 8 9 10 10 11 n 1 1 Same left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１１４】[0114]
【表６５】 化合物Ｎｏ． ３１１ ３１２ ３１３ ３１４ ３１５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 65 Compound No. 311 312 313 314 315 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same ring C 1 3-Fluoro- * 2 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１１５】[0115]
【表６６】 化合物Ｎｏ． ３１６ ３１７ ３１８ ３１９ ３２０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 66 Compound No. 316 317 318 319 320 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same ring C 1 3-Fluoro- * 2 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１１６】[0116]
【表６７】 化合物Ｎｏ． ３２１ ３２２ ３２３ ３２４ ３２５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は下記式（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 67 Compound No. 321 322 323 324 325 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same left Same as left Same Z 2 COO Same left Same as left Same left Same as left Ring A 1 2-Fluoro- * 7 Same left Same left Same left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same left ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left same left Ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 8 9 9 10 11 n 1 1 Same left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 7 2-Fluoro- represents a 2-fluoro-1,4-phenylene group represented by the following formula (E).
【化３２】 Embedded image
【０１１７】[0117]
【表６８】 化合物Ｎｏ． ３２６ ３２７ ３２８ ３２９ ３３０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は前記式（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 68 Compound No. 326 327 328 329 330 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Z 2 COO Same left Same as left Same left Same as left Ring A 1 2-Fluoro- * 7 Same left Same left Same as left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 7 2-Fluoro- represents the 2-fluoro-1,4-phenylene group of the above formula (E).
【０１１８】[0118]
【表６９】 化合物Ｎｏ． ３３１ ３３２ ３３３ ３３４ ３３５ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は前記式（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 69 Compound No. 331 332 333 334 335 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Z 2 COO Same left Same as left Same left Same as left Ring A 1 2-Fluoro- * 7 Same left Same left Same as left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 7 2-Fluoro- represents the 2-fluoro-1,4-phenylene group of the above formula (E).
【０１１９】[0119]
【表７０】 化合物Ｎｏ． ３３６ ３３７ ３３８ ３３９ ３４０ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 70 Compound No. 336 337 338 339 340 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same left Same as left Same Z 2 COO Same left Same as left Same left Same as left Ring A 1 3-Fluoro- * 2 Same left Same left Same left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１２０】[0120]
【表７１】 化合物Ｎｏ． ３４１ ３４２ ３４３ ３４４ ３４５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。Table 71 Compound No. 341 342 343 344 345 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same ring C 1 3-fluoro- * 2 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A).
【０１２１】[0121]
【表７２】 化合物Ｎｏ． ３４６ ３４７ ３４８ ３４９ ３５０ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は前記式（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 72 Compound No. 346 347 348 349 350 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Z 2 COO Same left Same as left Same left Same as left Ring A 1 2-Fluoro- * 7 Same left Same left Same as left Same left ring A 2 1,4-ph * 1 Same left Same left Same left Same ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 7 2-Fluoro- represents the 2-fluoro-1,4-phenylene group of the above formula (E).
【０１２２】[0122]
【表７３】 化合物Ｎｏ． ３５１ ３５２ ３５３ ３５４ ３５５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。Table 73 Compound No. 351 352 353 354 355 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same as left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 COO Same left Same left Same left Same left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 single bond Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【０１２３】[0123]
【表７４】 化合物Ｎｏ． ３５６ ３５７ ３５８ ３５９ ３６０ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。Table 74 Compound No. 356 357 358 359 360 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 single bond Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group.
【０１２４】[0124]
【表７５】 化合物Ｎｏ． ３６１ ３６２ ３６３ ３６４ ３６５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ 同左 同左 同左 同左 ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。Table 75 Compound No. 361 362 363 364 365 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 9 H 19 C 10 H 21 C 12 H 25 C 8 H 17 C 9 H 19 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 COO Same left Same left Same left Same left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 single bond Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 Same as at left Same as at left Same as at left Same as at left n 1 1 Same as at left Same as at left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group.
【０１２５】[0125]
【表７６】 化合物Ｎｏ． ３６６ ３６７ ３６８ ３６９ ３７０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は前記（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 76 Compound No. 366 367 368 369 370 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as on the left Same as left Z 1 single bond Same as left Same left same left Same left Z 2 single bond Same left same left Same left same left Same ring A 1 2-Fluoro- * 7 Same left same left Same left same left ring A 2 1,4-ph * 1 Same left same left Same left same left ring B 1 1,4 -ph same left same left same left same left ring B 2 1,4-ph same left same left same left same left ring C 1 1,4-ph same left same left same left same left ring C 2 1,4-ph same left same left same left same left m 7 8 9 10 10 11 n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 l, 4-ph is a 1,4-phenylene group It is. * 7 2-Fluoro-represents the 2-fluoro-1,4-phenylene group of the above (E).
【０１２６】[0126]
【表７７】 化合物Ｎｏ． ３７１ ３７２ ３７３ ３７４ ３７５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は前記（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 77 Compound No. 371 372 373 374 375 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as on the left Same as left Z 1 single bond Same as left Same left same left Same left Z 2 single bond Same left same left Same left same left Same ring A 1 2-Fluoro- * 7 Same left same left Same left same left ring A 2 1,4-ph * 1 Same left same left Same left same left ring B 1 1,4 -ph same left same left same left same left ring B 2 1,4-ph same left same left same left same left ring C 1 1,4-ph same left same left same left same left ring C 2 1,4-ph same left same left same left same left m 7 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 l, 4-ph is shown a 1,4-phenylene group . * 7 2-Fluoro-represents the 2-fluoro-1,4-phenylene group of the above (E).
【０１２７】[0127]
【表７８】 化合物Ｎｏ． ３７６ ３７７ ３７８ ３７９ ３８０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は前記（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 78 Compound No. 376 377 378 379 380 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as on the left Same as left Z 1 single bond Same as left Same left same left Same left Z 2 single bond Same left same left Same left same left Same ring A 1 2-Fluoro- * 7 Same left same left Same left same left ring A 2 1,4-ph * 1 Same left same left Same left same left ring B 1 1,4 -ph same left same left same left same left ring B 2 1,4-ph same left same left same left same left ring C 1 1,4-ph same left same left same left same left ring C 2 1,4-ph same left same left same left same left m 7 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 l, 4-ph is a 1,4-phenylene group Show. * 7 2-Fluoro-represents the 2-fluoro-1,4-phenylene group of the above (E).
【０１２８】[0128]
【表７９】 化合物Ｎｏ． ３８１ ３８２ ３８３ ３８４ ３８５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 2-フルオロ-＊7 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊7 2-フルオロ-は前記（Ｅ）の２−フルオロ−１，４−フェニレン基を示す。Table 79 Compound No. 381 382 383 384 385 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as on the left Same as left Z 1 single bond Same as left Same left same left Same left Z 2 single bond Same left same left Same left same left Same ring A 1 2-Fluoro- * 7 Same left same left Same left same left ring A 2 1,4-ph * 1 Same left same left Same left same left ring B 1 1,4 -ph same left same left same left same left ring B 2 1,4-ph same left same left same left same left ring C 1 1,4-ph same left same left same left same left ring C 2 1,4-ph same left same left same left same left m 7 7 7 7 7 7 n 1 1 Same left Same left Same left Same left Same left n 2 1 Same left Same left Same left Same left Same left * 1 1,4-ph represents 1,4-phenylene group You * 7 2-Fluoro-represents the 2-fluoro-1,4-phenylene group of the above (E).
【０１２９】[0129]
【表８０】 化合物Ｎｏ． ３８６ ３８７ ３８８ ３８９ ３９０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 80 Compound No. 386 387 388 389 390 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Z 2 COO Same as left Same as left Same as left Ring A 1 1,4-ph * 1 Same as left Same left Same left Same left Ring A 2 1,4-ph Same left Same left Same left Same left Same as left B 1 High-level 5 * 8 Same left Same as at left Same as at left Same as left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 8 9 10 11 n 1 1 Same as at left Same as at left indicates Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group . * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above (B).
【０１３０】[0130]
【表８１】 化合物Ｎｏ． ３９１ ３９２ ３９３ ３９４ ３９５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 81 Compound No. 391 392 393 394 395 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Z 2 COO Same as left Same left Same as left Same ring Same as left A 1 1,4-ph * 1 Same left Same left Same left Same left same ring A 2 1,4-ph Same left Same left Same left same left Same as left B 1 High-level -5 * 8 Same left Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same as left C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left same left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３１】[0131]
【表８２】 化合物Ｎｏ． ３９６ ３９７ ３９８ ３９９ ４００ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 82 Compound No. 396 397 398 399 400 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as left Same left Same left Same left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Z 2 COO Same as left Same left Same as left Same ring Same as left A 1 1,4-ph * 1 Same left Same left Same left Same left same ring A 2 1,4-ph Same left Same left Same left same left Same as left B 1 High-level -5 * 8 Same left Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same as left C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left same left the Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group It is. * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３２】[0132]
【表８３】 化合物Ｎｏ． ４０１ ４０２ ４０３ ４０４ ４０５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 83 Compound No. 401 402 402 403 404 405 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as left Same as left Same as left Same as left X 1 O Same left Same left Same left Same left Same left X 2 O Same left Same left Same left Same left Same left Y 1 Single bond Same left Same left Same left Same left Y 2 Single bond Same left Same left Same left Same as left Z 1 COO Same as left Same as left Same as left Z 2 COO Same as left Same left Same as left Same ring Same as left A 1 1,4-ph * 1 Same left Same left Same left Same left same ring A 2 1,4-ph Same left Same left Same left same left Same as left B 1 High-level -5 * 8 Same left Same as left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same as left C 1 1,4-ph Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left same left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group . * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３３】[0133]
【表８４】 化合物Ｎｏ． ４０６ ４０７ ４０８ ４０９ ４１０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 3-フルオロ-＊2 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 84 Compound No. 406 407 408 409 410 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 pin Rimijin -5 * 8 Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 3-Fluoro- * 2 Same left same left Same left same left m 7 8 9 9 10 11 n 1 1 Same as on the left Same as on the left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph 1,4 Shows the Eniren group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３４】[0134]
【表８５】 化合物Ｎｏ． ４１１ ４１２ ４１３ ４１４ ４１５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 3-フルオロ-＊2 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 85 Compound No. 411 412 413 414 415 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 pin Rimijin -5 * 8 Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 3-Fluoro- * 2 Same left same left Same left same left m 7 7 7 7 7 7 n 1 1 Same as on the left Same as on the left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-off Show a vinylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３５】[0135]
【表８６】 化合物Ｎｏ． ４１６ ４１７ ４１８ ４１９ ４２０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 3-フルオロ-＊2 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 86 Compound No. 416 417 418 419 420 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 pin Rimijin -5 * 8 Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 3-Fluoro- * 2 Same left same left Same left same left m 7 7 7 7 7 7 n 1 1 Same left Same left Same left Same left Same left n 2 1 Same left Same left Same left Same left Same left * 1 1,4-ph is 1,4- Shows a phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３６】[0136]
【表８７】 化合物Ｎｏ． ４２１ ４２２ ４２３ ４２４ ４２５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 3-フルオロ-＊2 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 87 Compound No. 421 422 423 424 425 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 pin Rimijin -5 * 8 Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left same ring C 2 3-Fluoro- * 2 Same left same left Same left same left m 7 7 7 7 7 7 n 1 1 Same as on the left Same as on the left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-off Show a vinylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３７】[0137]
【表８８】 化合物Ｎｏ． ４２６ ４２７ ４２８ ４２９ ４３０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 88 Compound No. 426 427 428 429 430 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 pin Rimijin -5 * 8 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 3-Fluoro- * 2 Same left same left Same left same left ring C 2 1,4-ph Same left same left Same left same left m 7 8 9 9 10 11 n 1 1 Same as on the left Same as on the left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph 1,4 Shows the Eniren group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３８】[0138]
【表８９】 化合物Ｎｏ． ４３１ ４３２ ４３３ ４３４ ４３５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 89 Compound No. 431 432 433 434 435 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 pin Rimijin -5 * 8 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 3-Fluoro- * 2 Same left same left Same left same left ring C 2 1,4-ph Same left same left Same left same left m 7 7 7 7 7 n 1 1 Same as on the left Same as on the left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-off Show a vinylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１３９】[0139]
【表９０】 化合物Ｎｏ． ４３６ ４３７ ４３８ ４３９ ４４０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 90 Compound No. 436 437 438 439 440 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 pin Rimijin -5 * 8 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 3-Fluoro- * 2 Same left same left Same left same left ring C 2 1,4-ph Same left same left Same left same left m 7 7 7 7 7 n 1 1 Same as on the left Same as on the left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph 1,4 Shows a phenylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１４０】[0140]
【表９１】 化合物Ｎｏ． ４４１ ４４２ ４４３ ４４４ ４４５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ヒ゜リミシ゛ン-5＊8 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊8 ヒ゜リミシ゛ン-5は前記式（Ｂ）のピリミジン−２，５−ジイル基を示す。Table 91 Compound No. 441 442 443 444 445 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 pin Rimijin -5 * 8 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 ph Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 3-Fluoro- * 2 Same left same left Same left same left ring C 2 1,4-ph Same left same left Same left same left m 7 7 7 7 7 n 1 1 Same as on the left Same as on the left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-off Show a vinylene group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 8 Polyimidin-5 represents the pyrimidine-2,5-diyl group of the above formula (B).
【０１４１】[0141]
【表９２】 化合物Ｎｏ． ４４６ ４４７ ４４８ ４４９ ４５０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 ０ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 92 Compound No. 446 447 448 449 450 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 None Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 2,6 naphth * 4 Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 8 9 10 11 n 1 0 Same as left Same as left Same as left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４２】[0142]
【表９３】 化合物Ｎｏ． ４５１ ４５２ ４５３ ４５４ ４５５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 93 Compound No. 451 452 453 454 455 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 None Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 2,6 naphth * 4 Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as at left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４３】[0143]
【表９４】 化合物Ｎｏ． ４５６ ４５７ ４５８ ４５９ ４６０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 94 Compound No. 456 457 458 459 460 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 None Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 2,6 naphth * 4 Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as at left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is shown a 1,4-phenylene group . * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４４】[0144]
【表９５】 化合物Ｎｏ． ４６１ ４６２ ４６３ ４６４ ４６５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 95 Compound No. 461 462 463 464 465 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 None Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 2,6 naphth * 4 Same as at left Same as at left Same as at left Same as at left ring B 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 1,4-ph Same as at left Same as at left Same as at left Same as at left ring C 2 1,4-ph Same as at left Same as at left Same as at left Same as at left m 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as at left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group. * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４５】[0145]
【表９６】 化合物Ｎｏ． ４６６ ４６７ ４６８ ４６９ ４７０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 ０ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 96 Compound No. 466 467 468 469 470 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as on the left Same as left Z 1 COO Same as left Same as left Same as left Same as left Z 2 Single bond Same as left Same left Same as left Same left ring A 1 None Same left Same left Same left Same left Same ring A 2 1,4-ph * 1 Same left Same left Same left Same left Same left ring B 1 2,6-Naphti * 4 Same left same left Same as left Same as left Ring B 2 1,4-ph Same as left Same left Same left Same left Same ring C 1 3-Fluoro- * 2 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 8 9 10 11 n 1 0 Same left Same left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is 1,4-phenylene Indicates a group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４６】[0146]
【表９７】 化合物Ｎｏ． ４７１ ４７２ ４７３ ４７４ ４７５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 97 Compound No. 471 472 473 474 475 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 None Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring B 1 2,6 naphth * 4 Same as at left Same as at left Same as at left Same as at left ring B 2 l, 4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 3- fluoro - * 2 Same as at left Same as at left Same as at left Same as at left ring C 2 l, 4-ph Same as at left Same as at left Same as at left Same as at left m 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group Indicates. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４７】[0147]
【表９８】 化合物Ｎｏ． ４７６ ４７７ ４７８ ４７９ ４８０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 98 Compound No. 476 477 478 479 480 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as on the left Same as left Z 1 COO Same as left Same as left Same as left Same as left Z 2 Single bond Same as left Same left Same as left Same left ring A 1 None Same left Same left Same left Same left Same ring A 2 1,4-ph * 1 Same left Same left Same left Same left Same left ring B 1 2,6-Naphti * 4 Same left same left Same as at left Same as at left ring B 2 l, 4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 3- fluoro - * 2 Same as at left Same as at left Same as at left Same as at left ring C 2 l, 4-ph Same as at left Same as at left Same as at left Same as at left m 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as on the left Same as on the left n 2 1 Same as on the left Same as on the left Same as on the left Same as on the left * 1 1,4-ph is 1,4-phenylene A group. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４８】[0148]
【表９９】 化合物Ｎｏ． ４８１ ４８２ ４８３ ４８４ ４８５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 ナシ 同左 同左 同左 同左 Ｙ2 ＣＯＯ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 単結合 同左 同左 同左 同左 環Ａ1 ナシ 同左 同左 同左 同左 環Ａ2 1,4-ph＊1 同左 同左 同左 同左 環Ｂ1 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 3-フルオロ-＊2 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊2 3-フルオロ-は前記式（Ａ）の３−フルオロ−１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 99 Compound No. 481 482 483 484 485 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 None Same as at left Same as at left Same as at left Same as at left Y 2 COO Same as at left Same as at left Same as on the left Same as left Z 1 COO Same as left Same as left Same as left Same as left Z 2 Single bond Same as left Same left Same as left Same left ring A 1 None Same left Same left Same left Same left Same ring A 2 1,4-ph * 1 Same left Same left Same left Same left Same left ring B 1 2,6-Naphti * 4 Same left same left Same as at left Same as at left ring B 2 l, 4-ph Same as at left Same as at left Same as at left Same as at left ring C 1 3- fluoro - * 2 Same as at left Same as at left Same as at left Same as at left ring C 2 l, 4-ph Same as at left Same as at left Same as at left Same as at left m 7 7 7 7 7 n 1 1 Same as at left Same as at left Same as at left Same as at left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is 1,4-phenylene It is shown. * 2 3-Fluoro- represents the 3-fluoro-1,4-phenylene group of the above formula (A). * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１４９】[0149]
【表１００】 化合物Ｎｏ． ４８６ ４８７ ４８８ ４８９ ４９０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 ナシ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 ナシ 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｃ1 2,6-ナフチ 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 ０ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 100 Compound No. 486 487 488 489 490 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 None Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 None Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left Ring B 2 2,6-Naphti * 4 Same as left Same left Same as left Same left Ring C 1 2,6-Naphti Same left Same left Same left Same left Same left Ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 8 9 10 11 n 1 0 Same left Same left Same left the Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group Show. * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１５０】[0150]
【表１０１】 化合物Ｎｏ． ４９１ ４９２ ４９３ ４９４ ４９５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 ナシ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 ナシ 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｃ1 2,6-ナフチ 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 101 Compound No. 491 492 493 494 495 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 None Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 None Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left Ring B 2 2,6-Naphti * 4 Same as left Same left Same as left Same left Ring C 1 2,6-Naft Same as left Same left Same left Same left Same as ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 n 1 1 Same left Same left Same left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is shown a 1,4-phenylene group You * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１５１】[0151]
【表１０２】 化合物Ｎｏ． ４９６ ４９７ ４９８ ４９９ ５００ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 ナシ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 ナシ 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｃ1 2,6-ナフチ 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 102 Compound No. 496 497 498 499 500 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 None Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 None Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left Ring B 2 2,6-Naphti * 4 Same as left Same left Same as left Same left Ring C 1 2,6-Naft Same as left Same left Same left Same left Same as ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 n 1 1 Same left Same left Same left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group Show. * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１５２】[0152]
【表１０３】 化合物Ｎｏ． ５０１ ５０２ ５０３ ５０４ ５０５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 ナシ 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 ナシ 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 2,6-ナフチ＊4 同左 同左 同左 同左 環Ｃ1 2,6-ナフチ 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊4 2,6-ナフチは２，６−ナフチレン基を示す。Table 103 Compound No. 501 502 503 504 505 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 None Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 None Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same as at left Same as at left Same as at left Same as at left Ring B 2 2,6-Naphti * 4 Same as left Same left Same as left Same left Ring C 1 2,6-Naft Same as left Same left Same left Same left Same as ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 n 1 1 Same left Same left Same left the Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph is a 1,4-phenylene group It is. * 4 2,6-naphthyl represents a 2,6-naphthylene group.
【０１５３】[0153]
【表１０４】 化合物Ｎｏ． ５０６ ５０７ ５０８ ５０９ ５１０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-シクロ＊3 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 ０ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 104 Compound No. 506 507 508 509 510 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4 cycloalkyl * 3 Same as at left Same as at left Same as at left Same as at left ring B 1 l, 4 -ph same left same left same left same left ring B 2 1,4-ph same left same left same left same left ring C 1 1,4-ph same left same left same left same left ring C 2 1,4-ph same left same left same left same left m 7 8 9 10 10 11 n 1 0 Same as left Same as left Same as left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１５４】[0154]
【表１０５】 化合物Ｎｏ． ５１１ ５１２ ５１３ ５１４ ５１５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-シクロ＊3 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 105 Compound No. 511 512 513 514 515 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 cyclo * 3 Same left Same left Same left Same left Same left ring B 2 1,4-ph Same left same left Same left same left ring C 1 1,4-ph Same left same left Same left same left Same left ring C 2 1,4-ph Same left same left Same left same left Same left m 7 7 7 7 7 7 n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１５５】[0155]
【表１０６】 化合物Ｎｏ． ５１６ ５１７ ５１８ ５１９ ５２０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-シクロ＊3 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 106 Compound No. 516 517 518 518 520 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 cyclo * 3 Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same ring C 1 1,4-ph Same left Same left Same left Same left Same ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same left Same left Same left Same left n 2 1 Same left Same left Same left Same left Same left * 1 1,4-ph represents 1,4-phenylene group . * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１５６】[0156]
【表１０７】 化合物Ｎｏ． ５２１ ５２２ ５２３ ５２４ ５２５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 Ｏ 同左 同左 同左 同左 Ｘ2 単結合 同左 同左 同左 同左 Ｙ1 単結合 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 ＣＯＯ 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-シクロ＊3 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-ph 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 107 Compound No. 521 522 523 524 525 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 O Same as at left Same as at left Same as at left Same as at left X 2 single bond Same as at left Same as at left Same as at left Same as at left Y 1 single bond Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as at left Same as at left Z 1 COO Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4 cyclo * 3 Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same ring C 1 1,4-ph Same left Same left Same left Same left Same ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１５７】[0157]
【表１０８】 化合物Ｎｏ． ５２６ ５２７ ５２８ ５２９ ５３０ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-シクロ＊3 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ８ ９ １０ １１ ｎ1 ０ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 108 Compound No. 526 527 528 529 530 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 C 9 H 19 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 C 8 H 17 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 a single bond Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same left ring C 1 1,4-Cyclo * 3 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 8 9 10 10 11 n 1 0 Same as left Same as left Same as left Same as left n 2 1 Same as at left Same as at left Same as at left Same as at left * 1 1,4-ph represents a 1,4-phenylene group * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１５８】[0158]
【表１０９】 化合物Ｎｏ． ５３１ ５３２ ５３３ ５３４ ５３５ Ｒ1 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ9Ｈ19 Ｃ8Ｈ17 Ｃ8Ｈ17 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-シクロ＊3 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 109 Compound No. 531 532 533 534 535 R 1 C 9 H 19 C 9 H 19 C 9 H 19 C 8 H 17 C 8 H 17 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 a single bond Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same ring C 1 1,4-cyclo * 3 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１５９】[0159]
【表１１０】 化合物Ｎｏ． ５３６ ５３７ ５３８ ５３９ ５４０ Ｒ1 Ｃ8Ｈ17 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ12Ｈ25 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｃ7Ｈ15 Ｃ10Ｈ21 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-シクロ＊3 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 110 Compound No. 536 537 538 538 540 R 1 C 8 H 17 C 10 H 21 C 10 H 21 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 12 H 25 C 10 H 21 C 12 H 25 C 7 H 15 C 10 H 21 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 a single bond Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same ring C 1 1,4-cyclo * 3 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same left Same left Same left Same left Same left n 2 1 Same left Same left Same left Same left Same left * 1 1,4-ph represents 1,4-phenylene group . * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１６０】[0160]
【表１１１】 化合物Ｎｏ． ５４１ ５４２ ５４３ ５４４ ５４５ Ｒ1 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ2 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｒ3 Ｃ7Ｈ15 Ｃ8Ｈ17 Ｃ9Ｈ19 Ｃ10Ｈ21 Ｃ12Ｈ25 Ｒ4 ＣＦ3又はＣＨ3 同左 同左 同左 同左 Ｘ1 単結合 同左 同左 同左 同左 Ｘ2 Ｏ 同左 同左 同左 同左 Ｙ1 ＣＯＯ 同左 同左 同左 同左 Ｙ2 単結合 同左 同左 同左 同左 Ｚ1 単結合 同左 同左 同左 同左 Ｚ2 ＣＯＯ 同左 同左 同左 同左 環Ａ1 1,4-ph＊1 同左 同左 同左 同左 環Ａ2 1,4-ph 同左 同左 同左 同左 環Ｂ1 1,4-ph 同左 同左 同左 同左 環Ｂ2 1,4-ph 同左 同左 同左 同左 環Ｃ1 1,4-シクロ＊3 同左 同左 同左 同左 環Ｃ2 1,4-ph 同左 同左 同左 同左 ｍ ７ ７ ７ ７ ７ ｎ1 １ 同左 同左 同左 同左 ｎ2 １ 同左 同左 同左 同左 ＊1 1,4-phは１，４−フェニレン基を示す。 ＊3 1,4-シクロは１，４−シクロヘキシレン基を示す。Table 111 Compound No. 541 542 543 544 545 R 1 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 2 CF 3 or CH 3 Same as left Same as left Same as left Same as left R 3 C 7 H 15 C 8 H 17 C 9 H 19 C 10 H 21 C 12 H 25 R 4 CF 3 or CH 3 Same as at left Same as at left Same as at left Same as at left X 1 single bond Same as at left Same as at left Same as at left Same as at left X 2 O Same as at left Same as at left Same as at left Same as at left Y 1 COO Same as at left Same as at left Same as at left Same as at left Y 2 single bond Same as at left Same as at left Same as on the left Same Z 1 a single bond Same as at left Same as at left Same as at left Same as at left Z 2 COO Same as at left Same as at left Same as at left Same as at left ring A 1 1,4-ph * 1 Same as at left Same as at left Same as at left Same as at left ring A 2 1,4-ph Same as at left Same as at left Same as at left Same as at left ring B 1 1,4-ph Same left Same left Same left Same left Same left Ring B 2 1,4-ph Same left Same left Same left Same left Same ring C 1 1,4-cyclo * 3 Same left Same left Same left Same left Same left ring C 2 1,4-ph Same left Same left Same left Same left Same left m 7 7 7 7 7 7 n 1 1 Same as left Same as left Same as left Same as left n 2 1 Same as left Same as left Same as left Same as left * 1 1,4-ph represents 1,4-phenylene group. * 3 1,4-Cyclo means a 1,4-cyclohexylene group.
【０１６１】[0161]
【実施例】以下に実施例を挙げて本発明を説明するが、
これにより限定されるものではない。The present invention will be described below with reference to examples.
It is not limited by this.
【０１６２】実施例１ （１）１，１，１，１１，１１，１１−ヘキサフルオロ
ウンデカン−２，１０−ジオールの合成Example 1 (1) Synthesis of 1,1,1,11,11,11-hexafluoroundecane-2,10-diol
【化３３】 マグネシウム（１．５ｇ，６２ｍｍｏｌ）に１，５−ジ
ブロモペンタン（７ｇ，３０ｍｍｏｌ）のテトラヒドロ
フラン（ＴＨＦ）（９０ｍｌ）溶液を滴下して、グリニ
ャール反応剤を調整した。これに、０℃でヨウ化銅
（Ｉ）（５００ｍｇ，２．６ｍｍｏｌ）をくわえ、さら
に１時間かけて、（Ｓ）−３，３，３−トリフルオロ−
１，２−エポキシプロパン（７５％ｅ．ｅ．，６．６
ｇ，５９ｍｍｏｌ）を滴下した。室温で３時間撹拌した
のち、２Ｍ塩酸で処理し、エーテル抽出、濃縮した。残
渣をシリカゲルクロマトグラフィー（ヘキサン／酢酸エ
チル＝５／１）で精製し、さらに蒸留（１１０℃／０．
１Ｔｏｒｒ）して、１，１，１，１１，１１，１１−ヘ
キサフルオロウンデカン−２，１０−ジオール〔２．６
ｇ収率２９％，（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／１〕を得
た。 無色油状物質1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．３０〜１．４８（ｍ，
８ Ｈ），１．５１〜１．７４（ｍ，６ Ｈ），２．０６
（ｄ，Ｊ＝６．２ Ｈｚ，２ Ｈ），３．９２（ｍ，２
Ｈ） ＩＲ（ｎｅａｔ）３４００，２９４０，２８７０，１２
８０，１１７０，１１４０，７００ｃｍ-1 Ｍａｓｓ ｍ／ｚ（相対強度）２９７（Ｍ+＋１，３
０），１３９（４６），９０（２８），７３（２４，７
０（２２），６９（２８），６８（２８），６７（３
２），５７（２２），５５（１００），４３（４１），
４２（２３），４１（８０），３９（２８），３１（２
５），２７（３２）[Chemical 33] A tetrahydrofuran (THF) (90 ml) solution of 1,5-dibromopentane (7 g, 30 mmol) was added dropwise to magnesium (1.5 g, 62 mmol) to prepare a Grignard reactant. Copper (I) iodide (500 mg, 2.6 mmol) was added thereto at 0 ° C., and (S) -3,3,3-trifluoro- was added over 1 hour.
1,2-epoxypropane (75% ee, 6.6
g, 59 mmol) was added dropwise. After stirring at room temperature for 3 hours, the mixture was treated with 2M hydrochloric acid, extracted with ether and concentrated. The residue was purified by silica gel chromatography (hexane / ethyl acetate = 5/1) and further distilled (110 ° C./0.
1 Torr) to give 1,1,1,11,11,11-hexafluoroundecane-2,10-diol [2.6
g yield 29%, (S, S) / (S, R) = 3/1] were obtained. Colorless oily substance 1 H NMR (CDCl 3 ) δ 1.30 to 1.48 (m,
8 H), 1.51 to 1.74 (m, 6 H), 2.06
(D, J = 6.2 Hz, 2 H), 3.92 (m, 2
H) IR (neat) 3400, 2940, 2870, 12
80, 1170, 1140, 700 cm -1 Mass m / z (relative intensity) 297 (M + + 1,3
0), 139 (46), 90 (28), 73 (24, 7)
0 (22), 69 (28), 68 (28), 67 (3
2), 57 (22), 55 (100), 43 (41),
42 (23), 41 (80), 39 (28), 31 (2
5), 27 (32)
【０１６３】（２）２，１０−ビス（４−ベンジルオキ
シフェニルカルボキシ）−１，１，１，１１，１１，１
１−ヘキサフルオロウンデカンの合成(2) 2,10-bis (4-benzyloxyphenylcarboxy) -1,1,1,11,11,1
Synthesis of 1-hexafluoroundecane
【化３４】 １，１，１，１１，１１，１１−ヘキサフルオロウンデ
カン−２，１０−ジオール〔２８０ｍｇ，０．９４ｍｍ
ｏｌ，（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／１〕と４−ベンジ
ルオキシ安息香酸（４８０ｍｇ，２．１ｍｍｏｌ）のジ
クロロメタン（２ｍｌ）懸濁液にポリリン酸エチル（Ｐ
ＰＥ）のクロロホルム溶液（３ｍｌ）を加え、室温で１
７時間撹拌した。反応液に飽和炭酸水素ナトリウム水溶
液を加え、エーテル抽出後、濃縮した。残渣をシリカゲ
ルカラムクロマトグラフィー（ヘキサン／酢酸エチル＝
９／１）で精製し、２，１０−ビス（４−ベンジルオキ
シフェニルカルボキシ）−１，１，１，１１，１１，１
１−ヘキサフルオロウンデカン〔４９４ｍｇ，収率７２
％，（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／１〕を得た。 無色油状物質1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２４〜１．４６（ｍ，
１０ Ｈ），１．８２（ｂｒｏａｄ ｑ，Ｊ＝７．３Ｈ
ｚ，４ Ｈ），５．１３（ｓ，４ Ｈ），５．５０（ｓｉ
ｘｔｅｔ，Ｊ＝６．８ Ｈｚ，２ Ｈ），７．０１（ｄ，
Ｊ＝９．０ Ｈｚ，４ Ｈ），７．３〜７．４２（ｍ，１
０ Ｈ），８．０２（ｄ，Ｊ＝９．０ Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）２９５０，２８８０，１７３０，１６
００，１５１０，１２６０，１１７０，１１００，１０
１０，８５０，７７０，７４０，７００ｃｍ-1 Ｍａｓｓ ｍ／ｚ（相対強度）７１８（Ｍ+＋２，ｔｒ
ａｃｅ），７１６（Ｍ+，ｔｒａｃｅ），３０２（３
４），２１１（５１），１２１（２１），９１（１０
０）Embedded image 1,1,1,11,11,11-hexafluoroundecane-2,10-diol [280 mg, 0.94 mm
Ol, (S, S) / (S, R) = 3/1] and 4-benzyloxybenzoic acid (480 mg, 2.1 mmol) in dichloromethane (2 ml) suspension in ethyl polyphosphate (P).
Chloroform solution of PE) (3 ml) was added, and 1
Stir for 7 hours. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ether and then concentrated. The residue was subjected to silica gel column chromatography (hexane / ethyl acetate =
9/1), 2,10-bis (4-benzyloxyphenylcarboxy) -1,1,1,11,11,1
1-hexafluoroundecane [494 mg, yield 72
%, (S, S) / (S, R) = 3/1] was obtained. Colorless oily substance 1 H NMR (CDCl 3 ) δ 1.24 to 1.46 (m,
10 H), 1.82 (broad q, J = 7.3 H)
z, 4 H), 5.13 (s, 4 H), 5.50 (si
xtet, J = 6.8 Hz, 2 H), 7.01 (d,
J = 9.0 Hz, 4 H), 7.3 to 7.42 (m, 1
0 H), 8.02 (d, J = 9.0 Hz, 4 H) IR (neat) 2950, 2880, 1730, 16
00, 1510, 1260, 1170, 1100, 10
10,850,770,740,700 cm -1 Mass m / z (relative intensity) 718 (M + +2, tr
ace), 716 (M + , trace), 302 (3
4), 211 (51), 121 (21), 91 (10
0)
【０１６４】（３）１，１，１，１１，１１，１１−ヘ
キサフルオロ−２，１０−ビス（４−ヒドロキシフェニ
ルカルボキシ）ウンデカンの合成(3) Synthesis of 1,1,1,11,11,11-hexafluoro-2,10-bis (4-hydroxyphenylcarboxy) undecane
【化３５】 ２，１０−ビス（４−ベンジルオキシフェニルカルボキ
シ）−１，１，１，１１，１１，１１−ヘキサフルオロ
ウンデカン（４００ｍｇ，０．５６ｍｍｏｌ，（Ｓ，
Ｓ）／（Ｓ，Ｒ）＝３／１〕、１０％パラジウム−炭素
（７０ｍｇ）の酢酸エチル（１０ｍｌ）懸濁液を水素雰
囲気下、室温で３時間処理した。反応液をセライトろ過
後、濃縮し、残渣をシリカゲルカラムクロマトグラフィ
ー（ヘキサン／酢酸エチル＝３／１）で精製し、１，
１，１，１１，１１，１１−ヘキサフルオロ−２，１０
−ビス（４−ヒドロキシフェニルカルボキシ）ウンデカ
ン〔２９６ｍｇ，収率９９％、（Ｓ，Ｓ）／（Ｓ，Ｒ）
＝３／１〕を得た。さらに、高速液体クロマトグラフィ
ー（ダイセル社，ＣＨＩＲＡＬＰＡＫ ＡＤ，ヘキサン
／２−プロパノール＝７／１）で（Ｓ，Ｓ）−１，１，
１，１１，１１，１１−ヘキサフルオロ−２，１０−ビ
ス（４−ヒドロキシフェニルカルボキシ）ウンデカンを
単離した。 無色油状物質 ［α］D 20−５８．８゜（ｃ＝１．０５，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２０〜１．４０（ｍ，
１０ Ｈ），１．８２（ｂｒｏａｄ ｑ，Ｊ＝７．３Ｈ
ｚ，４ Ｈ），５．４９（ｓｉｘｔｅｔ，Ｊ＝６．７ Ｈ
ｚ，２ Ｈ），５．５１（ｓ，２ Ｈ），６．８８（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ），７．９９（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）３４００，２９４０，１７００，１６
１０，１５１０，１４４０，１２６０，１１７０，１１
００，８５０，７７０，７００ｃｍ-1 Ｍａｓｓ ｍ／ｚ（相対強度）５３６（Ｍ+，ｔｒａｃ
ｅ），１３８（１５），１２１（１００）Embedded image 2,10-Bis (4-benzyloxyphenylcarboxy) -1,1,1,11,11,11-hexafluoroundecane (400 mg, 0.56 mmol, (S,
S) / (S, R) = 3/1], a suspension of 10% palladium-carbon (70 mg) in ethyl acetate (10 ml) was treated under a hydrogen atmosphere at room temperature for 3 hours. The reaction solution was filtered through Celite and concentrated, and the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 3/1).
1,1,11,11,11-hexafluoro-2,10
-Bis (4-hydroxyphenylcarboxy) undecane [296 mg, yield 99%, (S, S) / (S, R)
= 3/1] was obtained. Furthermore, by high performance liquid chromatography (Daicel, CHIRALPAK AD, hexane / 2-propanol = 7/1), (S, S) -1,1,
1,11,11,11-hexafluoro-2,10-bis (4-hydroxyphenylcarboxy) undecane was isolated. Colorless oily substance [α] D 20 −58.8 ° (c = 1.05, CHCl 3 ) 1 H NMR (CDCl 3 ) δ1.20 to 1.40 (m,
10 H), 1.82 (broad q, J = 7.3 H)
z, 4 H), 5.49 (sixtet, J = 6.7 H)
z, 2 H), 5.51 (s, 2 H), 6.88 (d,
J = 8.8 Hz, 4 H), 7.99 (d, J = 8.8)
Hz, 4 H) IR (neat) 3400, 2940, 1700, 16
10, 1510, 1440, 1260, 1170, 11
00,850,770,700 cm -1 Mass m / z (relative intensity) 536 (M + , trac
e), 138 (15), 121 (100)
【０１６５】（４）（Ｓ，Ｓ）−１，１，１，１１，１
１，１１−ヘキサフルオロ−２，１０−ビス［４−｛４
−（４−オクチルオキシフェニル）フェニルカルボキ
シ｝フェニルカルボキシ］ウンデカン（式〔II〕の化合
物）の合成(4) (S, S) -1,1,1,11,1
1,11-hexafluoro-2,10-bis [4- {4
Synthesis of-(4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (compound of formula [II])
【化３６】 （Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス（４−ヒドロキシフェニルカル
ボキシ）ウンデカン（１００ｍｇ，０．１９ｍｍｏ
ｌ）、４−（４−オクチルオキシフェニル）安息香酸
（１２５ｍｇ，０．３８ｍｍｏｌ）、ジシクロヘキシル
カルボジイミド（ＤＣＣ）（１１５ｍｇ，０．５６ｍｍ
ｏｌ）、４−ジメチルアミノピリジン（３０ｍｇ，０．
２４ｍｍｏｌ）のジクロロメタン（６ｍｌ）溶液を室温
で７時間撹拌した。反応溶液をセライトろ過、濃縮後、
残渣をシリカゲルカラムクロマトグラフィー（ヘキサン
／ジクロロメタン＝２／１）で精製し、さらに再結晶
（ヘキサン／ジクロロメタン＝１０／１）して、（Ｓ，
Ｓ）−１，１，１，１１，１１，１１−ヘキサフルオロ
−２，１０−ビス［４−｛４−（４−オクチルオキシフ
ェニル）フェニルカルボキシ｝フェニルカルボキシ］ウ
ンデカン（１７２ｍｇ，収率８０％）（式〔Ｘ〕の化合
物）を得た。無色粉末。 相転移温度Embedded image (S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis (4-hydroxyphenylcarboxy) undecane (100 mg, 0.19 mmo
1), 4- (4-octyloxyphenyl) benzoic acid (125 mg, 0.38 mmol), dicyclohexylcarbodiimide (DCC) (115 mg, 0.56 mm)
ol), 4-dimethylaminopyridine (30 mg, 0.
A solution of 24 mmol) in dichloromethane (6 ml) was stirred at room temperature for 7 hours. The reaction solution was filtered through Celite and concentrated,
The residue was purified by silica gel column chromatography (hexane / dichloromethane = 2/1) and recrystallized (hexane / dichloromethane = 10/1) to give (S,
S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (172 mg, yield 80% ) (Compound of formula [X]). Colorless powder. Phase transition temperature
【表１１２】 ［α］D 20−３９．８゜（ｃ＝１．０５，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ０．９０（ｔ，Ｊ＝７．０
Ｈｚ，６ Ｈ），１．２４〜１．５４（ｍ，３０ Ｈ），
１．７７〜１．９０（ｍ，８ Ｈ），４．０１（ｔ，Ｊ
＝６．６ Ｈｚ，４ Ｈ），５．５５（ｓｉｘｔｅｔ，Ｊ
＝６．６ Ｈｚ，２ Ｈ），７．００（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ），７．３６（ｄ，Ｊ＝８．８ Ｈｚ，４
Ｈ），７．５９（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），７．
７０（ｄ，Ｊ＝８．６ Ｈｚ，４ Ｈ），８．１７（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ），８．２３（ｄ，Ｊ＝８．６
Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）２９３０，１７４０，１６００，１２６
０，１１８０，１１６０，８３０，７７０ｃｍ-1 元素分析：Ｃ67Ｈ74Ｏ10Ｆ6として計算値：Ｃ，６９．
７８：Ｈ，６．４７％、実測値：Ｃ，６９．８９：Ｈ，
６．４９％[Table 112] [Α] D 20 -39.8 ° (c = 1.05, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 7.0
Hz, 6 H), 1.24 to 1.54 (m, 30 H),
1.77 to 1.90 (m, 8 H), 4.01 (t, J
= 6.6 Hz, 4 H), 5.55 (sixtet, J
= 6.6 Hz, 2 H), 7.00 (d, J = 8.8)
Hz, 4 H), 7.36 (d, J = 8.8 Hz, 4
H), 7.59 (d, J = 8.8 Hz, 4 H), 7.
70 (d, J = 8.6 Hz, 4 H), 8.17 (d,
J = 8.8 Hz, 4 H), 8.23 (d, J = 8.6
Hz, 4 H) IR (KBr) 2930, 1740, 1600, 126
0,1180,1160,830,770 cm −1 Elemental analysis: Calculated as C 67 H 74 O 10 F 6 : C, 69.
78: H, 6.47%, measured value: C, 69.89: H,
6.49%
【０１６６】（５）（Ｒ）−３−フルオロ−４−ヘキサ
デカノイルビフェニル−４′−カルボン酸 ４−（１−
トリフルオロメチルノニルオキシカルボニル）フェニル
（化合物Ａ）のヒステリシス改善剤として前記式〔Ｘ〕
の化合物の添加 （Ｒ）−３−フルオロ−４−ヘキサデカノイルビフェニ
ル−４′−カルボン酸４−（１−トリフルオロメチルノ
ニルオキシカルボニル）フェニル（化合物Ａ）に、
（Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス［４−｛４−（４−オクチルオ
キシフェニル）フェニルカルボキシ｝フェニルカルボキ
シ］ウンデカン（式〔Ｘ〕で示す）を重量比で５％添加
した時のヒステリシスの改善効果を検討した。（Ｒ）−
３−フルオロ−４−ヘキサデカノイルビフェニル−４′
−カルボン酸 ４−（１−トリフルオロメチルノニルオ
キシカルボニル）フェニル（化合物Ａ）の相転移温度は(5) (R) -3-Fluoro-4-hexadecanoylbiphenyl-4'-carboxylic acid 4- (1-
As a hysteresis improving agent for trifluoromethylnonyloxycarbonyl) phenyl (Compound A), the above formula [X]
To the compound (R) -3-fluoro-4-hexadecanoylbiphenyl-4'-carboxylic acid 4- (1-trifluoromethylnonyloxycarbonyl) phenyl (Compound A),
(S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (formula [X ]) Was added in an amount of 5% by weight, and the effect of improving the hysteresis was examined. (R)-
3-fluoro-4-hexadecanoylbiphenyl-4 '
-The phase transition temperature of carboxylic acid 4- (1-trifluoromethylnonyloxycarbonyl) phenyl (Compound A) is
【表１１３】 であり、（Ｓ，Ｓ）−１，１，１，１１，１１，１１−
ヘキサフルオロ−２，１０−ビス［４−｛４−（４−オ
クチルオキシフェニル）フェニルカルボキシ｝フェニル
カルボキシ］ウンデカン（式〔Ｘ〕の化合物）を重量比
で５％添加した混合物の相転移温度は[Table 113] And (S, S) -1,1,1,11,11,11-
The phase transition temperature of a mixture obtained by adding 5% by weight of hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (compound of formula [X]) is:
【表１１４】 である。ラビング処理したポリイミド配向膜を透明電極
基板上に有するセル厚２μｍの液晶セルに（Ｒ）−３−
フルオロ−４−ヘキサデカノイルビフェニル−４′−カ
ルボン酸 ４−（１−トリフルオロメチルノニルオキシ
カルボニル）フェニル（化合物Ａ）単独あるいは、
（Ｒ）−３−フルオロ−４−ヘキサデカノイルビフェニ
ル−４′−カルボン酸 ４−（１−トリフルオロメチル
ノニルオキシカルボニル）フェニル（化合物Ａ）：
（Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス［４−｛４−（４−オクチルオ
キシフェニル）フェニルカルボキシ｝フェニルカルボキ
シ］ウンデカン（式〔Ｘ〕の化合物）＝９５：５を等方
相において充填し、液晶薄膜セルを作製した。８０Ｖｐ
ｐ、１Ｈｚの三角波を印加したときの化合物Ａの透過光
強度と印加電圧曲線を図４の上段に示す。（Ｒ）−３−
フルオロ−４−ヘキサデカノイルビフェニル−４′−カ
ルボン酸 ４−（１−トリフルオロメチルノニルオキシ
カルボニル）フェニル（化合物Ａ）単独の５０．０℃に
おけるヒステリシスは図４の下段に示す通りであり、無
電界状態からプラス方向、マイナス方向のいずれかにわ
ずかに電圧を加えるだけで暗状態を維持することができ
なくなる。これに対して、（Ｒ）−３−フルオロ−４−
ヘキサデカノイルビフェニル−４′−カルボン酸 ４−
（１−トリフルオロメチルノニルオキシカルボニル）フ
ェニル（化合物Ａ）：（Ｓ，Ｓ）−１，１，１，１１，
１１，１１−ヘキサフルオロ−２，１０−ビス［４−
｛４−（４−オクチルオキシフェニル）フェニルカルボ
キシ｝フェニルカルボキシ］ウンデカン（式〔Ｘ〕の化
合物）＝９５：５で混和した混合物の５０．０℃におけ
るヒステリシスは図５に示す通りである。無電界状態か
らプラス方向、マイナス方向に３０Ｖ程度の電圧を印加
しても暗状態を維持することができる。従って、（Ｓ，
Ｓ）−１，１，１，１１，１１，１１−ヘキサフルオロ
−２，１０−ビス［４−｛４−（４−オクチルオキシフ
ェニル）フェニルカルボキシ｝フェニルカルボキシ］ウ
ンデカン（式〔Ｘ〕の化合物）を添加することにより相
転移温度をほとんど変化させることなく、化合物Ａのヒ
ステリシスを改善することができる。[Table 114] Is. A liquid crystal cell having a cell thickness of 2 μm and having a rubbing-treated polyimide alignment film on a transparent electrode substrate is (R) -3-
Fluoro-4-hexadecanoylbiphenyl-4'-carboxylic acid 4- (1-trifluoromethylnonyloxycarbonyl) phenyl (Compound A) alone or
(R) -3-Fluoro-4-hexadecanoylbiphenyl-4′-carboxylic acid 4- (1-trifluoromethylnonyloxycarbonyl) phenyl (Compound A):
(S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (formula [X ]) = 95: 5 in the isotropic phase to prepare a liquid crystal thin film cell. 80Vp
The transmitted light intensity and the applied voltage curve of Compound A when a triangular wave of p, 1 Hz is applied are shown in the upper part of FIG. (R) -3-
The hysteresis of fluoro-4-hexadecanoylbiphenyl-4'-carboxylic acid 4- (1-trifluoromethylnonyloxycarbonyl) phenyl (Compound A) alone at 50.0 ° C. is as shown in the lower part of FIG. The dark state cannot be maintained by applying a slight voltage in either the positive direction or the negative direction from the non-electric field state. On the other hand, (R) -3-fluoro-4-
Hexadecanoylbiphenyl-4'-carboxylic acid 4-
(1-Trifluoromethylnonyloxycarbonyl) phenyl (Compound A): (S, S) -1,1,1,11,
11,11-hexafluoro-2,10-bis [4-
The hysteresis at 50.0 ° C. of the mixture of {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (compound of formula [X]) = 95: 5 is shown in FIG. The dark state can be maintained even when a voltage of about 30 V is applied in the positive and negative directions from the no-electric field state. Therefore, (S,
S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (compound of formula [X] Addition of () can improve the hysteresis of the compound A with almost no change in the phase transition temperature.
【０１６７】実施例２ （１）１，１，１，１２，１２，１２−ヘキサフルオロ
ドデカン−２，１１−ジオールの合成Example 2 (1) Synthesis of 1,1,1,12,12,12-hexafluorododecane-2,11-diol
【化３７】 １，１，１，１１，１１，１１−ヘキサフルオロウンデ
カン−２，１０−ジオールの合成と同様な条件下、マグ
ネシウム（２．４ｇ，９８ｍｍｏｌ）、１，６−ジブロ
モヘキサン（１０．９ｇ，４５ｍｍｏｌ）、ヨウ化銅
（Ｉ）（８２０ｍｇ，４．３ｍｍｏｌ）、（Ｓ）−３，
３，３−トリフルオロ−１，２−エポキシプロパン（７
５％ｅ．ｅ．，１０ｇ，８９ｍｍｏｌ）より、１，１，
１，１２，１２，１２−ヘキサフルオロドデカン−２，
１１−ジオール〔６．１ｇ，収率４４％，（Ｓ，Ｓ）／
（Ｓ，Ｒ）＝３／１〕を得た。 無色固体 融点５４−７０℃ 沸点１２０℃／０．２Ｔ
ｏｒｒ1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２８〜１．４８（ｍ，
１０ Ｈ），１．５１〜１．７６（ｍ，６ Ｈ），２．０
３（ｄ，Ｊ＝５．２ Ｈｚ，２ Ｈ），３．９１（ｍ，２
Ｈ） ＩＲ（ＫＢｒ）３３００，２９００，１２７０，１１７
０，１１２０，６９０ｃｍ-1 （２）２，１１−ビス（４−ベンジルオキシフェニルカ
ルボキシ）−１，１，１，１２，１２，１２−ヘキサフ
ルオロドデカンの合成[Chemical 37]1,1,1,11,11,11-hexafluorounde
Under conditions similar to the synthesis of can-2,10-diol, the mag
Nesium (2.4 g, 98 mmol), 1,6-dibroth
Mohexane (10.9 g, 45 mmol), copper iodide
(I) (820 mg, 4.3 mmol), (S) -3,
3,3-trifluoro-1,2-epoxypropane (7
5% e. e. , 10 g, 89 mmol), 1,1,
1,12,12,12-hexafluorododecane-2,
11-diol [6.1 g, yield 44%, (S, S) /
(S, R) = 3/1] was obtained. Colorless solid, melting point 54-70 ° C, boiling point 120 ° C / 0.2T
orr1 1 H NMR (CDCl3) Δ 1.28 to 1.48 (m,
10 H), 1.51 to 1.76 (m, 6 H), 2.0
3 (d, J = 5.2 Hz, 2 H), 3.91 (m, 2
H) IR (KBr) 3300, 2900, 1270, 117
0,1120,690 cm-1 (2) 2,11-bis (4-benzyloxyphenylcarba)
Ruboxi) -1,1,1,12,12,12-hexaf
Synthesis of Luorododecane
【化３８】 ２，１０−ビス（４−ベンジルオキシフェニルカルボキ
シ）−１，１，１，１１，１１，１１−ヘキサフルオロ
ウンデカンの合成と同様な条件下、１，１，１，１２，
１２，１２−ヘキサフルオロドデカン−２，１１−ジオ
ール（３０６ｍｇ，０．９９ｍｍｏｌ，（Ｓ，Ｓ）／
（Ｓ，Ｒ）＝３／１）、４−ベンジルオキシ安息香酸
（５０８ｍｇ，２．２ｍｍｏｌ）から、２，１１−ビス
（４−ベンジルオキシフェニルカルボキシ）−１，１，
１，１２，１２，１２−ヘキサフルオロドデカン（６９
４ｍｇ，収率９６％、（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／
１）を得た。 無色油状物質1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２０〜１．４２（ｍ，
１２ Ｈ），１．８３（ｂｒｏａｄ ｑ，Ｊ＝７．３ Ｈ
ｚ，４ Ｈ），５．１３（ｓ，４ Ｈ），５．５１（ｓｉ
ｘｔｅｓ，Ｊ＝６．７ Ｈｚ，２ Ｈ），７．０１（ｄ，
Ｊ＝９．０ Ｈｚ，４ Ｈ），７．３２〜７．４４（ｍ，
１０ Ｈ），８．０２（ｄ，Ｊ＝９．０Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）２９３０，１７３０，１６００，１５
１０，１２５０，１１７０，１１００，８５０，７７
０，７００ｃｍ-1 Ｍａｓｓ ｍ／ｚ（相対強度）７３１（Ｍ+＋１，ｔｒ
ａｃｅ），７３０（Ｍ+，ｔｒａｃｅ），３０１（１
４），２１１（２７），１２１（１９），９１（１０
０） （３）１，１，１，１２，１２，１２−ヘキサフルオロ
−２，１１−ビス（４−ヒドロキシフェニルカルボキ
シ）ドデカン[Chemical 38] Under the same conditions as in the synthesis of 2,10-bis (4-benzyloxyphenylcarboxy) -1,1,1,11,11,11-hexafluoroundecane, 1,1,1,12,
12,12-Hexafluorododecane-2,11-diol (306 mg, 0.99 mmol, (S, S) /
(S, R) = 3/1), 4-benzyloxybenzoic acid (508 mg, 2.2 mmol) to 2,11-bis (4-benzyloxyphenylcarboxy) -1,1,
1,12,12,12-hexafluorododecane (69
4 mg, yield 96%, (S, S) / (S, R) = 3 /
1) was obtained. Colorless oily substance 1 H NMR (CDCl 3 ) δ1.20 to 1.42 (m,
12 H), 1.83 (broad q, J = 7.3 H)
z, 4 H), 5.13 (s, 4 H), 5.51 (si
xtes, J = 6.7 Hz, 2 H), 7.01 (d,
J = 9.0 Hz, 4 H), 7.32 to 7.44 (m,
10 H), 8.02 (d, J = 9.0 Hz, 4 H) IR (neat) 2930, 1730, 1600, 15
10, 1250, 1170, 1100, 850, 77
0,700 cm -1 Mass m / z (relative intensity) 731 (M + +1, tr
ace), 730 (M + , trace), 301 (1
4), 211 (27), 121 (19), 91 (10)
0) (3) 1,1,1,12,12,12-hexafluoro-2,11-bis (4-hydroxyphenylcarboxy) dodecane
【化３９】 １，１，１，１１，１１，１１−ヘキサフルオロ−２，
１０−ビス（４−ヒドロキシフェニルカルボキシ）ウン
デカンの合成と同様な条件下、２，１１−ビス（４−ベ
ンジルオキシフェニルカルボキシ）−１，１，１，１
２，１２，１２−ヘキサフルオロドデカン（６１０ｍ
ｇ，０．８３ｍｍｏｌ，（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／
１）より、１，１，１，１２，１２，１２−ヘキサフル
オロ−２，１１−ビス（４−ヒドロキシフェニルカルボ
キシ）ドデカン（４６５ｍｇ，収率１００％，（Ｓ，
Ｓ）／（Ｓ，Ｒ）＝３／１）を得た。さらに、高速液体
クロマトグラフィー（ダイセル社，ＣＨＩＲＡＬＰＡＫ
ＡＤ，ヘキサン／２−プロパノール＝７／１）で
（Ｓ，Ｓ）−１，１，１，１２，１２，１２−ヘキサフ
ルオロ−２，１１−ビス（４−ヒドロキシフェニルカル
ボキシ）ドデカンを単離した。 無色固体 融点１１２℃ ［α］D 20−５３．５゜（ｃ＝１．０４，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．１８〜１．４２（ｍ，
１２ Ｈ），１．８３（ｂｒｏａｄ ｑ，Ｊ＝７．３Ｈ
ｚ，４ Ｈ），５．４９（ｓｉｘｔｅｔ，Ｊ＝６．７ Ｈ
ｚ，２ Ｈ），５．６５（ｓ，２ Ｈ），６．８９（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ），７．９９（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）３４００，２９２０，２８５０，１７０
０，１６００，１５９０，１５１０，１２８０，１２６
０，１２３０，１１８０，１１６０，１１３０，１１２
０，１１００，８５０，７７０，７００，６２０ｃｍ-1 Ｍａｓｓ ｍ／ｚ（相対強度）５５０（Ｍ+，ｔｒａｃ
ｅ），１３８（１２），１２１（１００） （４）（Ｓ，Ｓ）−１，１，１，１２，１２，１２−ヘ
キサフルオロ−２，１１−ビス［４−｛４−（４−オク
チルオキシフェニル）フェニルカルボキシ｝フェニルカ
ルボキシ］ドデカン（式〔XI〕の化合物）の合成[Chemical Formula 39] 1,1,1,11,11,11-hexafluoro-2,
2,11-bis (4-benzyloxyphenylcarboxy) -1,1,1,1 under the same conditions as in the synthesis of 10-bis (4-hydroxyphenylcarboxy) undecane
2,12,12-Hexafluorododecane (610m
g, 0.83 mmol, (S, S) / (S, R) = 3 /
From 1), 1,1,1,12,12,12-hexafluoro-2,11-bis (4-hydroxyphenylcarboxy) dodecane (465 mg, yield 100%, (S,
S) / (S, R) = 3/1) was obtained. Furthermore, high performance liquid chromatography (Daicel, CHIRALPAK
Isolation of (S, S) -1,1,1,12,12,12-hexafluoro-2,11-bis (4-hydroxyphenylcarboxy) dodecane with AD, hexane / 2-propanol = 7/1) did. Colorless solid, mp 112 ℃ [α] D 20 -53.5 ° (c = 1.04, CHCl 3) 1 H NMR (CDCl 3) δ1.18~1.42 (m,
12 H), 1.83 (broad q, J = 7.3 H)
z, 4 H), 5.49 (sixtet, J = 6.7 H)
z, 2 H), 5.65 (s, 2 H), 6.89 (d,
J = 8.8 Hz, 4 H), 7.99 (d, J = 8.8)
Hz, 4 H) IR (KBr) 3400, 2920, 2850, 170
0, 1600, 1590, 1510, 1280, 126
0, 1230, 1180, 1160, 1130, 112
0, 1100, 850, 770, 700, 620 cm -1 Mass m / z (relative intensity) 550 (M + , trac
e), 138 (12), 121 (100) (4) (S, S) -1,1,1,12,12,12-hexafluoro-2,11-bis [4- {4- (4- Synthesis of octyloxyphenyl) phenylcarboxy} phenylcarboxy] dodecane (compound of formula [XI])
【化４０】 （Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス［４−｛４−（４−オクチルオ
キシフェニル）フェニルカルボキシ｝フェニルカルボキ
シ］ウンデカンの合成と同様な条件下、（Ｓ，Ｓ）−
１，１，１，１２，１２，１２−ヘキサフルオロ−２，
１１−ビス（４−ヒドロキシフェニルカルボキシ）ドデ
カン（１３９ｍｇ，０．２５ｍｍｏｌ）、４−（４−オ
クチルオキシフェニル）安息香酸（１７８ｍｇ，０．５
５ｍｍｏｌ）、ＤＣＣ（１２５ｍｇ，０．６１ｍｍｏ
ｌ）、４−ジメチルアミノピリジン（３５ｍｇ，０．２
９ｍｍｏｌ）から、（Ｓ，Ｓ）−１，１，１，１２，１
２，１２−ヘキサフルオロ−２，１１−ビス［４−｛４
−（４−オクチルオキシフェニル）フェニルカルボキ
シ｝フェニルカルボキシ］ドデカン（式〔XI〕の化合
物）（２２２ｍｇ，収率７５％）を得た。 無色粉末 相転移温度[Chemical 40] Similar to the synthesis of (S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (S, S)-
1,1,1,12,12,12-hexafluoro-2,
11-bis (4-hydroxyphenylcarboxy) dodecane (139 mg, 0.25 mmol), 4- (4-octyloxyphenyl) benzoic acid (178 mg, 0.5
5 mmol), DCC (125 mg, 0.61 mmo
l), 4-dimethylaminopyridine (35 mg, 0.2
9 mmol) to (S, S) -1,1,1,12,1
2,12-hexafluoro-2,11-bis [4- {4
There was obtained-(4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] dodecane (compound of formula [XI]) (222 mg, yield 75%). Colorless powder phase transition temperature
【表１１５】 ［α］D 20−３９．０゜（ｃ＝１．０１，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ０．９０（ｔ，Ｊ＝７．０
Ｈｚ，６ Ｈ），１．２４〜１．５４（ｍ，３２ Ｈ），
１．７７〜１．９２（ｍ，８ Ｈ），４．０２（ｔ，Ｊ
＝６．６ Ｈｚ，４ Ｈ），５．５５（ｓｉｘｔｅｔ，Ｊ
＝６．６ Ｈｚ，２ Ｈ），７．０１（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ），７．３６（ｄ，Ｊ＝８．８ Ｈｚ，４
Ｈ），７．５９（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），７．
７０（ｄ，Ｊ＝８．６ Ｈｚ，４ Ｈ），８．１７（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ），８．２３（ｄ，Ｊ＝８．６
Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）２９３０，１７３５，１６００，１２６
０，１１８０，１１６０，１０７０，８３０，７７０ｃ
ｍ-1 元素分析：Ｃ68Ｈ76Ｏ10Ｆ6として計算値：Ｃ，６９．
９７：Ｈ，６．５６％、実測値：Ｃ，７０．０８：Ｈ，
６．５２％ （５）前記式〔Ｘ〕の化合物と前記式〔XI〕の化合物と
を混合することによる反強誘電性の強さの制御。 （Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス［４−｛４−（４−オクチルオ
キシフェニル）フェニルカルボキシ｝フェニルカルボキ
シ］ウンデカン（式〔Ｘ〕の化合物）は反強誘電性液晶
であるものの２μｍ程度のセル厚のガラスセルに液晶を
注入した場合には、４００Ｖｐｐ程度の印加電圧では電
界誘起の相転移を起こすには不十分であり、三安定状態
間スイッチングを観察することはできない。（Ｓ，Ｓ）
−１，１，１，１２，１２，１２−ヘキサフルオロ−
２，１１−ビス［４−｛４−（４−オクチルオキシフェ
ニル）フェニルカルボキシ｝フェニルカルボキシ］ウン
デカン（式〔XI〕の化合物）は強誘電性液晶であり、
（Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス［４−｛４−（４−オクチルオ
キシフェニル）フェニルカルボキシ｝フェニルカルボキ
シ］ウンデカン（式〔Ｘ〕の化合物）と（Ｓ，Ｓ）−
１，１，１，１２，１２，１２−ヘキサフルオロ−２，
１１−ビス［４−｛４−（４−オクチルオキシフェニ
ル）フェニルカルボキシ｝フェニルカルボキシ］ドデカ
ン（式〔XI〕の化合物）を混合することによって、反強
誘電性の強さをコントロールすることができる。そこで
ラビング処理したポリイミド配向膜を透明電極基板上に
有するセル厚２μｍの液晶セルに（Ｓ，Ｓ）−１，１，
１，１１，１１，１１−ヘキサフルオロ−２，１０−ビ
ス［４−｛４−（４−オクチルオキシフェニル）フェニ
ルカルボキシ｝フェニルカルボキシ］ウンデカン（式
〔Ｘ〕の化合物）と（Ｓ，Ｓ）−１，１，１，１２，１
２，１２−ヘキサフルオロ−２，１１−ビス［４−｛４
−（４−オクチルオキシフェニル）フェニルカルボキ
シ｝フェニルカルボキシ］ドデカン（式〔XI〕の化合
物）を４５：５５（重量比）の割合で混和した混合物を
等方相において充填し、液晶薄膜セルを作製した。１５
５℃においてこの液晶セルに２５０Ｖｐｐ、０．１Ｈｚ
の三角波を印加したときの透過光強度と印加電圧曲線は
図６に示すように、三安定状態間のスイッチングを示す
ことにより、混合系は反強誘電性であることがわかる。[Table 115] [Α] D 20 -39.0 ° (c = 1.01, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 7.0
Hz, 6 H), 1.24 to 1.54 (m, 32 H),
1.77 to 1.92 (m, 8 H), 4.02 (t, J
= 6.6 Hz, 4 H), 5.55 (sixtet, J
= 6.6 Hz, 2 H), 7.01 (d, J = 8.8)
Hz, 4 H), 7.36 (d, J = 8.8 Hz, 4
H), 7.59 (d, J = 8.8 Hz, 4 H), 7.
70 (d, J = 8.6 Hz, 4 H), 8.17 (d,
J = 8.8 Hz, 4 H), 8.23 (d, J = 8.6
Hz, 4 H) IR (KBr) 2930, 1735, 1600, 126
0,1180,1160,1070,830,770c
m -1 Elemental analysis: C 68 H 76 O 10 F 6 Calculated: C, 69.
97: H, 6.56%, measured value: C, 70.08: H,
6.52% (5) Control of antiferroelectric strength by mixing the compound of the formula [X] and the compound of the formula [XI]. (S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (formula [X Compound) is an antiferroelectric liquid crystal, but when the liquid crystal is injected into a glass cell having a cell thickness of about 2 μm, an applied voltage of about 400 Vpp is insufficient to cause an electric field-induced phase transition, It is not possible to observe switching between tristable states. (S, S)
-1,1,1,12,12,12-hexafluoro-
2,11-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (compound of formula [XI]) is a ferroelectric liquid crystal,
(S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (formula [X ] Compound) and (S, S)-
1,1,1,12,12,12-hexafluoro-2,
By mixing 11-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] dodecane (compound of formula [XI]), the strength of antiferroelectricity can be controlled. . Therefore, in a liquid crystal cell having a cell thickness of 2 μm, which has a rubbing-treated polyimide alignment film on a transparent electrode substrate, (S, S) -1,1,
1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (compound of formula [X]) and (S, S) -1,1,1,12,1
2,12-hexafluoro-2,11-bis [4- {4
A liquid crystal thin film cell was prepared by filling a mixture of 45-55 (weight ratio) of-(4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] dodecane (compound of formula [XI]) in an isotropic phase. did. 15
250 Vpp, 0.1 Hz in this liquid crystal cell at 5 ° C
As shown in FIG. 6, the transmitted light intensity and the applied voltage curve when the triangular wave is applied show switching between the tristable states, which indicates that the mixed system is antiferroelectric.
【０１６８】実施例３ （１）１，１，１，１３，１３，１３−ヘキサフルオロ
トリデカン−２，１２−ジオールの合成Example 3 (1) Synthesis of 1,1,1,13,13,13-hexafluorotridecane-2,12-diol
【化４１】 １，１，１，１１，１１，１１−ヘキサフルオロウンデ
カン−２，１０−ジオールの合成と同様な条件下、マグ
ネシウム（１．５ｇ，６２ｍｍｏｌ）、１，７−ジブロ
モヘプタン（８．０ｇ，３１ｍｍｏｌ）、ヨウ化銅
（Ｉ）（５００ｍｇ，２．６ｍｍｏｌ）、（Ｓ）−３，
３，３−トリフルオロ−１，２−エポキシプロパン（７
５％ｅ．ｅ．，６．５ｇ，５８ｍｍｏｌ）より、１，
１，１，１３，１３，１３−ヘキサフルオロトリデカン
−２，１２−ジオール〔３．８ｇ、収率３８％，（Ｓ，
Ｓ）／（Ｓ，Ｒ）＝３／１〕を得た。 無色油状物質 沸点１２０℃／０．１Ｔｏｒｒ1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２６〜１．４８（ｍ，
１２ Ｈ），１．５２〜１．７６（ｍ，６ Ｈ），１．９
９（ｄ，Ｊ＝６．２ Ｈｚ，２ Ｈ），３．９１（ｍ，２
Ｈ） ＩＲ（ＫＢｒ）３３００，２９２０，２８６０，１２８
０，１１７０，７００ｃｍ-1 （２）２，１２−ビス（４−ベンジルオキシフェニルカ
ルボキシ）−１，１，１，１３，１３，１３−ヘキサフ
ルオロトリデカンの合成Embedded image Under the same conditions as in the synthesis of 1,1,1,11,11,11-hexafluoroundecane-2,10-diol, magnesium (1.5 g, 62 mmol), 1,7-dibromoheptane (8.0 g, 31 mmol). ), Copper (I) iodide (500 mg, 2.6 mmol), (S) -3,
3,3-trifluoro-1,2-epoxypropane (7
5% e. e. , 6.5 g, 58 mmol), 1,
1,1,13,13,13-hexafluorotridecane-2,12-diol [3.8 g, yield 38%, (S,
S) / (S, R) = 3/1] was obtained. Colorless oily substance Boiling point 120 ° C / 0.1 Torr 1 H NMR (CDCl 3 ) δ 1.26 to 1.48 (m,
12 H), 1.52 to 1.76 (m, 6 H), 1.9.
9 (d, J = 6.2 Hz, 2 H), 3.91 (m, 2
H) IR (KBr) 3300, 2920, 2860, 128
0,1170,700 cm -1 (2) Synthesis of 2,12-bis (4-benzyloxyphenylcarboxy) -1,1,1,13,13,13-hexafluorotridecane
【化４２】 ２，１０−ビス（４−ベンジルオキシフェニルカルボキ
シ）−１，１，１，１１，１１，１１−ヘキサフルオロ
ウンデカンの合成と同様な条件下、１，１，１，１３，
１３，１３−ヘキサフルオロトリデカン−２，１２−ジ
オール（３１５ｍｇ，０．９４ｍｍｏｌ，（Ｓ，Ｓ）／
（Ｓ，Ｒ）＝３／１）、４−ベンジルオキシ安息香酸
（５２０ｍｇ，２．３ｍｍｏｌ）から、２，１２−ビス
（４−ベンジルオキシフェニルカルボキシ）−１，１，
１，１３，１３，１３−ヘキサフルオロトリデカン（７
３６ｍｇ，収率１００％、（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３
／１）を得た。 無色油状物質1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２０〜１．４２（ｍ，
１４ Ｈ），１．８４（ｂｒｏａｄ ｑ，Ｊ＝７．３ Ｈ
ｚ，４ Ｈ），５．１３（ｓ，４ Ｈ），５．５１（ｓｉ
ｘｔｅｔ，Ｊ＝６．７ Ｈｚ，２ Ｈ），７．０１（ｄ，
Ｊ＝９．０ Ｈｚ，４ Ｈ），７．３２〜７．４５（ｍ，
１０ Ｈ），８．０２（ｄ，Ｊ＝９．０Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）２９２０，２８５０，１７２５，１６
００，１５１０，１２５０，１１７０，１１００，８４
５，７７０，７００ｃｍ-1 （３）１，１，１，１３，１３，１３−ヘキサフルオロ
−２，１２−ビス（４−ヒドロキシフェニルカルボキ
シ）トリデカンEmbedded image Under the same conditions as in the synthesis of 2,10-bis (4-benzyloxyphenylcarboxy) -1,1,1,11,11,11-hexafluoroundecane, 1,1,1,13,
13,13-Hexafluorotridecane-2,12-diol (315 mg, 0.94 mmol, (S, S) /
(S, R) = 3/1), 4-benzyloxybenzoic acid (520 mg, 2.3 mmol) to 2,12-bis (4-benzyloxyphenylcarboxy) -1,1,
1,13,13,13-hexafluorotridecane (7
36 mg, yield 100%, (S, S) / (S, R) = 3
/ 1) was obtained. Colorless oily substance 1 H NMR (CDCl 3 ) δ1.20 to 1.42 (m,
14 H), 1.84 (broad q, J = 7.3 H)
z, 4 H), 5.13 (s, 4 H), 5.51 (si
xtet, J = 6.7 Hz, 2 H), 7.01 (d,
J = 9.0 Hz, 4 H), 7.32 to 7.45 (m,
10 H), 8.02 (d, J = 9.0 Hz, 4 H) IR (neat) 2920, 2850, 1725, 16
00, 1510, 1250, 1170, 1100, 84
5,770,700 cm -1 (3) 1,1,1,13,13,13-hexafluoro-2,12-bis (4-hydroxyphenylcarboxy) tridecane
【化４３】 １，１，１，１１，１１，１１−ヘキサフルオロ−２，
１０−ビス（４−ヒドロキシフェニルカルボキシ）ウン
デカンの合成と同様な条件下、２，１２−ビス（４−ベ
ンジルオキシフェニルカルボキシ）−１，１，１，１
３，１３，１３−ヘキサフルオロトリデカン（７００ｍ
ｇ，０．９４ｍｍｏｌ，（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／
１）より、１，１，１，１３，１３，１３−ヘキサフル
オロ−２，１２−ビス（４−ヒドロキシフェニルカルボ
キシ）トリデカン（５１９ｍｇ，収率９８％，（Ｓ，
Ｓ）／（Ｓ，Ｒ）＝３／１）を得た。さらに、高速液体
クロマトグラフィー（ダイセル社，ＣＨＩＲＡＬＰＡＫ
ＡＤ，ヘキサン／２−プロパノール＝７／１）で
（Ｓ，Ｓ）−１，１，１，１３，１３，１３−ヘキサフ
ルオロ−２，１２−ビス（４−ヒドロキシフェニルカル
ボキシ）トリデカンを単離した。 無色油状物質 ［α］D 20−４７．８゜（ｃ＝１．０４，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．１７〜１．４２（ｍ，
１４ Ｈ），１．８４（ｂｒｏａｄ ｑ，Ｊ＝７．３Ｈ
ｚ，４ Ｈ），５．５０（ｓｉｘｔｅｔ，Ｊ＝６．７ Ｈ
ｚ，２ Ｈ），５．９２（ｓ，２ Ｈ），６．８９（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ），７．９９（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）３４００，１９２０，２８５０，１７０
０，１６００，１５１０，１４４０，１２６０，１１６
０，１１１０，８５０，７６０，７００ｃｍ-1 Ｍａｓｓ ｍ／ｚ（相対強度）５６４（Ｍ+，ｔｒａｃ
ｅ），１４９（１４），１３８（１７），１２１（１０
０），５７（１５），５５（１５），４５（１１），４
３（１７），４１（１８） （４）（Ｓ，Ｓ）−１，１，１，１３，１３，１３−ヘ
キサフルオロ−２，１２−ビス［４−｛４−（４−オク
チルオキシフェニル）フェニルカルボキシ｝フェニルカ
ルボキシ］トリデカン（式〔XII〕の化合物）の合成[Chemical 43] 1,1,1,11,11,11-hexafluoro-2,
2,12-bis (4-benzyloxyphenylcarboxy) -1,1,1,1 under the same conditions as in the synthesis of 10-bis (4-hydroxyphenylcarboxy) undecane
3,13,13-Hexafluorotridecane (700m
g, 0.94 mmol, (S, S) / (S, R) = 3 /
From 1), 1,1,1,13,13,13-hexafluoro-2,12-bis (4-hydroxyphenylcarboxy) tridecane (519 mg, yield 98%, (S,
S) / (S, R) = 3/1) was obtained. Furthermore, high performance liquid chromatography (Daicel, CHIRALPAK
Isolation of (S, S) -1,1,1,13,13,13-hexafluoro-2,12-bis (4-hydroxyphenylcarboxy) tridecane with AD, hexane / 2-propanol = 7/1) did. Colorless oily substance [α] D 20 −47.8 ° (c = 1.04, CHCl 3 ) 1 H NMR (CDCl 3 ) δ1.17 to 1.42 (m,
14 H), 1.84 (broad q, J = 7.3 H)
z, 4 H), 5.50 (sixtet, J = 6.7 H)
z, 2 H), 5.92 (s, 2 H), 6.89 (d,
J = 8.8 Hz, 4 H), 7.99 (d, J = 8.8)
Hz, 4 H) IR (KBr) 3400, 1920, 2850, 170
0, 1600, 1510, 1440, 1260, 116
0, 1110, 850, 760, 700 cm -1 Mass m / z (relative intensity) 564 (M + , trac)
e), 149 (14), 138 (17), 121 (10)
0), 57 (15), 55 (15), 45 (11), 4
3 (17), 41 (18) (4) (S, S) -1,1,1,1,13,13,13-hexafluoro-2,12-bis [4- {4- (4-octyloxyphenyl) ) Phenylcarboxy} phenylcarboxy] tridecane (compound of formula [XII])
【化４４】 （Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス［４−｛４−（４−オクチルオ
キシフェニル）フェニルカルボキシ｝フェニルカルボキ
シ］ウンデカンの合成と同様な条件下、（Ｓ，Ｓ）−
１，１，１，１３，１３，１３−ヘキサフルオロ−２，
１２−ビス（４−ヒドロキシフェニルカルボキシ）トリ
デカン（１０３ｍｇ，０．１８ｍｍｏｌ）、４−（４−
オクチルオキシフェニル）安息香酸（１１９ｍｇ，０．
３６ｍｍｏｌ）、ＤＣＣ（１０２ｍｇ，０．４９ｍｍｏ
ｌ）、４−ジメチルアミノピリジン（３０ｍｇ，０．２
５ｍｍｏｌ）から、（Ｓ，Ｓ）−１，１，１，１３，１
３，１３−ヘキサフルオロ−２，１２−ビス［４−｛４
−（４−オクチルオキシフェニル）フェニルカルボキ
シ｝フェニルカルボキシ］トリデカン（式〔XII〕の化
合物）（１５３ｍｇ，収率７１％）を得た。 無色粉末 相転移温度[Chemical 44] Similar to the synthesis of (S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (S, S)-
1,1,1,13,13,13-hexafluoro-2,
12-bis (4-hydroxyphenylcarboxy) tridecane (103 mg, 0.18 mmol), 4- (4-
Octyloxyphenyl) benzoic acid (119 mg, 0.
36 mmol), DCC (102 mg, 0.49 mmo
l), 4-dimethylaminopyridine (30 mg, 0.2
5 mmol) to (S, S) -1,1,1,13,1
3,13-hexafluoro-2,12-bis [4- {4
There was obtained-(4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] tridecane (compound of formula [XII]) (153 mg, yield 71%). Colorless powder phase transition temperature
【表１１６】 ［α］D 20−３３．８゜（ｃ＝１．０１，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ０．９０（ｔ，Ｊ＝７．０
Ｈｚ，６ Ｈ），１．２３〜１．５３（ｍ，３４ Ｈ），
１．７７〜１．９２（ｍ，８ Ｈ），４．０１（ｔ，Ｊ
＝６．６ Ｈｚ，４ Ｈ），５．５５（ｓｉｘｔｅｔ，Ｊ
＝６．６ Ｈｚ，２ Ｈ），７．０１（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ），７．３６（ｄ，Ｊ＝８．８ Ｈｚ，４
Ｈ），７．５９（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），７．
７０（ｄ，Ｊ＝８．６ Ｈｚ，４ Ｈ），８．１７（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ），８．２３（ｄ，Ｊ＝８．６
Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）２９２０，２８５０，１７３０，１６０
０，１２６０，１１７５，１１６０，１１１０，１０６
０，８３０，７６５ｃｍ-1 元素分析：Ｃ69Ｈ78Ｏ10Ｆ6として計算値：Ｃ，７０．
１５：Ｈ，６．６６％、実測値：Ｃ，７０．１５：Ｈ，
６．８０％[Table 116] [Α] D 20 -33.8 ° (c = 1.01, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 7.0
Hz, 6 H), 1.23 to 1.53 (m, 34 H),
1.77 to 1.92 (m, 8 H), 4.01 (t, J
= 6.6 Hz, 4 H), 5.55 (sixtet, J
= 6.6 Hz, 2 H), 7.01 (d, J = 8.8)
Hz, 4 H), 7.36 (d, J = 8.8 Hz, 4
H), 7.59 (d, J = 8.8 Hz, 4 H), 7.
70 (d, J = 8.6 Hz, 4 H), 8.17 (d,
J = 8.8 Hz, 4 H), 8.23 (d, J = 8.6
Hz, 4 H) IR (KBr) 2920, 2850, 1730, 160
0, 1260, 1175, 1160, 1110, 106
0,830,765 cm −1 Elemental analysis: C 69 H 78 O 10 F 6 Calculated value: C, 70.
15: H, 6.66%, measured value: C, 70.15: H,
6.80%
【０１６９】実施例４ （１）１，１，１，１５，１５，１５−ヘキサフルオロ
ペンタデカン−２，１４−ジオールの合成Example 4 (1) Synthesis of 1,1,1,15,15,15-hexafluoropentadecane-2,14-diol
【化４５】 １，１，１，１１，１１，１１−ヘキサフルオロウンデ
カン−２，１０−ジオールの合成と同様な条件下、マグ
ネシウム（２．１ｇ，８６ｍｍｏｌ）、１，９−ジブロ
モノナン（１０ｇ，３５ｍｍｏｌ）、ヨウ化銅（Ｉ）
（７００ｍｇ，３．７ｍｍｏｌ）、（Ｓ）−３，３，３
−トリフルオロ−１，２−エポキシプロパン（７５％
ｅ．ｅ．，１０ｇ，８９ｍｍｏｌ）より、１，１，１，
１５，１５，１５−ヘキサフルオロペンタデカン−２，
１４−ジオール〔５．４ｇ、収率４４％，（Ｓ，Ｓ）／
（Ｓ，Ｒ）＝３／１〕を得た。 無色柱状晶 融点３０〜３８℃ 沸点１５０℃／０．２
Ｔｏｒｒ1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２２〜１．４６（ｍ，
１６ Ｈ），１．５２〜１．７６（ｍ，６ Ｈ），２．０
４（ｄ，Ｊ＝６．２ Ｈｚ，２ Ｈ），３．９１（ｍ，２
Ｈ） ＩＲ（ＫＢｒ）３３７０，２９２０，２８５０，１２７
５，１１７０，１１４０，６９５ｃｍ-1 （２）２，１４−ビス（４−ベンジルオキシフェニルカ
ルボキシ）−１，１，１，１５，１５，１５−ヘキサフ
ルオロペンタデカンの合成Embedded image1,1,1,11,11,11-hexafluorounde
Under conditions similar to the synthesis of can-2,10-diol, the mag
Nesium (2.1 g, 86 mmol), 1,9-dibroth
Mononan (10 g, 35 mmol), copper (I) iodide
(700 mg, 3.7 mmol), (S) -3,3,3
-Trifluoro-1,2-epoxypropane (75%
e. e. , 10 g, 89 mmol), 1,1,1,
15,15,15-hexafluoropentadecane-2,
14-diol [5.4 g, yield 44%, (S, S) /
(S, R) = 3/1] was obtained. Colorless columnar crystals, melting point 30-38 ° C, boiling point 150 ° C / 0.2
Torr1 1 H NMR (CDCl3) Δ1.22 to 1.46 (m,
16 H), 1.52 to 1.76 (m, 6 H), 2.0
4 (d, J = 6.2 Hz, 2 H), 3.91 (m, 2
H) IR (KBr) 3370, 2920, 2850, 127
5,1170,1140,695cm-1 (2) 2,14-bis (4-benzyloxyphenyl)
Ruboxi) -1,1,1,15,15,15-hexaf
Synthesis of Luoropentadecane
【化４６】 ２，１０−ビス（４−ベンジルオキシフェニルカルボキ
シ）−１，１，１，１１，１１，１１−ヘキサフルオロ
ウンデカンの合成と同様な条件下、１，１，１，１５，
１５，１５−ヘキサフルオロペンタデカン−２，１４−
ジオール（４３５ｍｇ，１．２ｍｍｏｌ，（Ｓ，Ｓ）／
（Ｓ，Ｒ）＝３／１）、４−ベンジルオキシ安息香酸
（６２５ｍｇ，２．７ｍｍｏｌ）から、２，１４−ビス
（４−ベンジルオキシフェニルカルボキシ）−１，１，
１，１５，１５，１５−ヘキサフルオロペンタデカン
（８６１ｍｇ，収率９０％、（Ｓ，Ｓ）／（Ｓ，Ｒ）＝
３／１）を得た。 無色油状物質1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．１８〜１．４６（ｍ，
１８ Ｈ），１．８４（ｂｒｏａｄ ｑ，Ｊ＝７．３ Ｈ
ｚ，４ Ｈ），５．１３（ｓ，４ Ｈ），５．５１（ｓｉ
ｘｔｅｔ，Ｊ＝６．７ Ｈｚ，２ Ｈ），７．０２（ｄ，
Ｊ＝９．０ Ｈｚ，４ Ｈ），７．３２〜７．４６（ｍ，
１０ Ｈ），８．０２（ｄ，Ｊ＝９．０Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）２９４０，２８６０，１７３０，１６
００，１５１０，１２６０，１１７０，７７０，７００
ｃｍ-1 （３）１，１，１，１５，１５，１５−ヘキサフルオロ
−２，１４−ビス（４−ヒドロキシフェニルカルボキ
シ）ペンタデカン[Chemical formula 46]2,10-bis (4-benzyloxyphenylcarboxy)
Si) -1,1,1,11,11,11-hexafluoro
Under the same conditions as the synthesis of undecane, 1,1,1,15,
15,15-Hexafluoropentadecane-2,14-
Diol (435 mg, 1.2 mmol, (S, S) /
(S, R) = 3/1), 4-benzyloxybenzoic acid
From (625 mg, 2.7 mmol), 2,14-bis
(4-benzyloxyphenylcarboxy) -1,1,
1,15,15,15-hexafluoropentadecane
(861 mg, yield 90%, (S, S) / (S, R) =
3/1) was obtained. Colorless oily substance1 1 H NMR (CDCl3) Δ 1.18 to 1.46 (m,
18 H), 1.84 (broad q, J = 7.3 H)
z, 4 H), 5.13 (s, 4 H), 5.51 (si
xtet, J = 6.7 Hz, 2 H), 7.02 (d,
J = 9.0 Hz, 4 H), 7.32 to 7.46 (m,
10 H), 8.02 (d, J = 9.0 Hz, 4 H) IR (neat) 2940, 2860, 1730, 16
00, 1510, 1260, 1170, 770, 700
cm-1 (3) 1,1,1,15,15,15-hexafluoro
-2,14-bis (4-hydroxyphenylcarboxy)
Si) Pentadecane
【化４７】 １，１，１，１１，１１，１１−ヘキサフルオロ−２，
１０−ビス（４−ヒドロキシフェニルカルボキシ）ウン
デカンの合成と同様な条件下、２，１４−ビス（４−ベ
ンジルオキシフェニルカルボキシ）−１，１，１，１
５，１５，１５−ヘキサフルオロペンタデカン（７９８
ｍｇ，１．０３ｍｍｏｌ，（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３
／１）より、１，１，１，１５，１５，１５−ヘキサフ
ルオロ−２，１４−ビス（４−ヒドロキシフェニルカル
ボキシ）ペンタデカン（５９１ｍｇ，収率９６％，
（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／１）を得た。さらに、高
速液体クロマトグラフィー（ダイセル社，ＣＨＩＲＡＬ
ＰＡＫ ＡＤ，ヘキサン／２−プロパノール＝６：１）
で（Ｓ，Ｓ）−１，１，１，１５，１５，１５−ヘキサ
フルオロ−２，１４−ビス（４−ヒドロキシフェニルカ
ルボキシ）ペンタデカンを単離した。 無色油状物質1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．１６〜１．４４（ｍ，
１８ Ｈ），１．８５（ｂｒｏａｄ ｑ，Ｊ＝７．３Ｈ
ｚ，４ Ｈ），５．５１（ｓｉｘｔｅｔ，Ｊ＝６．７ Ｈ
ｚ，２ Ｈ），６．１４（ｂｒｏａｄ ｓ，２ Ｈ），
６．９０（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），７．９９
（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）３４００，２９４０，２８６０，１７
００，１６１０，１５１０，１２６０，１１７０，１１
１０，８５０，７７０，７００ｃｍ-1 （４）（Ｓ，Ｓ）−１，１，１，１５，１５，１５−ヘ
キサフルオロ−２，１４−ビス［４−｛４−（４−オク
チルオキシフェニル）フェニルカルボキシ｝フェニルカ
ルボキシ］ペンタデカン（式〔XIII〕）の合成[Chemical 47]1,1,1,11,11,11-hexafluoro-2,
10-bis (4-hydroxyphenylcarboxy) un
Under the same conditions as in the synthesis of decane, 2,14-bis (4-beta)
Benzyloxyphenylcarboxy) -1,1,1,1
5,15,15-Hexafluoropentadecane (798
mg, 1.03 mmol, (S, S) / (S, R) = 3
/ 1,), 1,1,1,15,15,15-hexaph
Luoro-2,14-bis (4-hydroxyphenylcal)
Boxy) pentadecane (591 mg, yield 96%,
(S, S) / (S, R) = 3/1) was obtained. Furthermore, high
High-performance liquid chromatography (Daicel, CHIRAL)
PAK AD, hexane / 2-propanol = 6: 1)
And (S, S) -1,1,1,15,15,15-hexa
Fluoro-2,14-bis (4-hydroxyphenyl)
Luboxy) pentadecane was isolated. Colorless oily substance1 1 H NMR (CDCl3) Δ 1.16 to 1.44 (m,
18 H), 1.85 (broad q, J = 7.3 H)
z, 4 H), 5.51 (sixtet, J = 6.7 H
z, 2 H), 6.14 (broad s, 2 H),
6.90 (d, J = 8.8 Hz, 4 H), 7.99
(D, J = 8.8 Hz, 4 H) IR (neat) 3400, 2940, 2860, 17
00, 1610, 1510, 1260, 1170, 11
10,850,770,700cm-1 (4) (S, S) -1,1,1,15,15,15-F
Xafluoro-2,14-bis [4- {4- (4-octane
Cyloxyphenyl) phenylcarboxy} phenylca
Synthesis of ruboxy] pentadecane (formula [XIII])
【化４８】（Ｓ，Ｓ）−１，１，１，１１，１１，１１
−ヘキサフルオロ−２，１０−ビ ス［４−｛４−（４−オクチルオキシフェニル）フェニ
ルカルボキシ｝フェニルカルボキシ］ウンデカンの合成
と同様な条件下、（Ｓ，Ｓ）−１，１，１，１５，１
５，１５−ヘキサフルオロ−２，１４−ビス（４−ヒド
ロキシフェニルカルボキシ）ペンタデカン（１３９ｍ
ｇ，０．２３ｍｍｏｌ）、４−（４−オクチルオキシフ
ェニル）安息香酸（１５５ｍｇ，０．４７ｍｍｏｌ）、
ＤＣＣ（１２５ｍｇ，０．６１ｍｍｏｌ）、４−ジメチ
ルアミノピリジン（２５ｍｇ，０．２０ｍｍｏｌ）か
ら、（Ｓ，Ｓ）−１，１，１，１５，１５，１５−ヘキ
サフルオロ−２，１４−ビス［４−｛４−（４−オクチ
ルオキシフェニル）フェニルカルボキシ｝フェニルカル
ボキシ］ペンタデカン（式〔XIII〕の化合物）（２０７
ｍｇ，収率７３％）を得た。 無色粉末 相転移温度(S, S) -1,1,1,11,11,11
-Hexafluoro-2,10-bi (S, S) -1,1,1,15,1 under the same conditions as the synthesis of su [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane.
5,15-Hexafluoro-2,14-bis (4-hydroxyphenylcarboxy) pentadecane (139m
g, 0.23 mmol), 4- (4-octyloxyphenyl) benzoic acid (155 mg, 0.47 mmol),
From DCC (125 mg, 0.61 mmol) and 4-dimethylaminopyridine (25 mg, 0.20 mmol), (S, S) -1,1,1,15,15,15-hexafluoro-2,14-bis [ 4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] pentadecane (compound of formula [XIII]) (207
mg, yield 73%) was obtained. Colorless powder phase transition temperature
【表１１７】 ［α］D 20３８．３゜（ｃ＝１．０１，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ０．９０（ｔ，Ｊ＝７．０
Ｈｚ，６ Ｈ），１．２０〜１．５３（ｍ，３８ Ｈ），
１．７７〜１．９２（ｍ，８ Ｈ），４．０１（ｔ，Ｊ
＝６．６ Ｈｚ，４ Ｈ），５．５５（ｓｉｘｔｅｔ，Ｊ
＝６．６ Ｈｚ，２ Ｈ），７．０１（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ），７．３６（ｄ，Ｊ＝８．８ Ｈｚ，４
Ｈ），７．６０（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），７．
７０（ｄ，Ｊ＝８．６ Ｈｚ，４ Ｈ），８．１７（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ）、８．２３（ｄ，Ｊ＝８．６
Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）２９３０，２８５０，１７３５，１６０
０，１２６０，１１６０，１１１５，１１６５，８３
０，７６５ｃｍ-1 [Table 117] [Α] D 20 38.3 ° (c = 1.01, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 7.0
Hz, 6 H), 1.20 to 1.53 (m, 38 H),
1.77 to 1.92 (m, 8 H), 4.01 (t, J
= 6.6 Hz, 4 H), 5.55 (sixtet, J
= 6.6 Hz, 2 H), 7.01 (d, J = 8.8)
Hz, 4 H), 7.36 (d, J = 8.8 Hz, 4
H), 7.60 (d, J = 8.8 Hz, 4 H), 7.
70 (d, J = 8.6 Hz, 4 H), 8.17 (d,
J = 8.8 Hz, 4 H), 8.23 (d, J = 8.6
Hz, 4 H) IR (KBr) 2930, 2850, 1735, 160
0, 1260, 1160, 1115, 1165, 83
0,765 cm -1
【０１７０】実施例５ （１）１，１，１，１６，１６，１６−ヘキサフルオロ
ヘキサデカン−２，１５−ジオールの合成Example 5 (1) Synthesis of 1,1,1,16,16,16-hexafluorohexadecane-2,15-diol
【化４９】 １，１，１，１１，１１，１１−ヘキサフルオロウンデ
カン−２，１０−ジオールの合成と同様な条件下、マグ
ネシウム（２．０ｇ，８２ｍｍｏｌ）、１，１０−ジブ
ロモデカン（１１ｇ，３７ｍｍｏｌ）、ヨウ化銅（Ｉ）
（７００ｍｇ，３．７ｍｍｏｌ）、（Ｓ）−３，３，３
−トリフルオロ−１，２−エポキシプロパン（７５％
ｅ．ｅ．，１０ｇ，８９ｍｍｏｌ）より、１，１，１，
１６，１６，１６−ヘキサフルオロヘキサデカン−２，
１５−ジオール〔７．０ｇ、収率５２％，（Ｓ，Ｓ）／
（Ｓ，Ｒ）＝３／１〕を得た。 無色粉末 沸点１５０℃／０．２Ｔｏｒｒ1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．２３〜１．４８（ｍ，
１８ Ｈ），１．５２〜１．７６（ｍ，６ Ｈ），２．０
１（ｄ，Ｊ＝６．３ Ｈｚ，２ Ｈ），３．９１（ｍ，２
Ｈ） ＩＲ（ＫＢｒ）３３３０，２９２０，２８５０，１２８
０，１１７０，１１３０，７００ｃｍ-1 （２）２，１５−ビス（４−ベンジルオキシフェニルカ
ルボキシ）−１，１，１，１６，１６，１６−ヘキサフ
ルオロヘキサデカンの合成[Chemical 49]1,1,1,11,11,11-hexafluorounde
Under conditions similar to the synthesis of can-2,10-diol, the mag
Nesium (2.0 g, 82 mmol), 1,10-dib
Romodecane (11 g, 37 mmol), copper (I) iodide
(700 mg, 3.7 mmol), (S) -3,3,3
-Trifluoro-1,2-epoxypropane (75%
e. e. , 10 g, 89 mmol), 1,1,1,
16,16,16-hexafluorohexadecane-2,
15-diol [7.0 g, yield 52%, (S, S) /
(S, R) = 3/1] was obtained. Colorless powder, boiling point 150 ° C / 0.2 Torr1 1 H NMR (CDCl3) Δ1.23 to 1.48 (m,
18 H), 1.52 to 1.76 (m, 6 H), 2.0
1 (d, J = 6.3 Hz, 2 H), 3.91 (m, 2
H) IR (KBr) 3330, 2920, 2850, 128
0,1170,1130,700cm-1 (2) 2,15-bis (4-benzyloxyphenyl)
Ruboxi) -1,1,1,16,16,16-hexaf
Synthesis of Luorohexadecane
【化５０】 ２，１０−ビス（４−ベンジルオキシフェニルカルボキ
シ）−１，１，１，１１，１１，１１−ヘキサフルオロ
ウンデカンの合成と同様な条件下、１，１，１，１６，
１６，１６−ヘキサフルオロヘキサデカン−２，１５−
ジオール（６００ｍｇ，１．６ｍｍｏｌ，（Ｓ，Ｓ）／
（Ｓ，Ｒ）＝３／１）、４−ベンジルオキシ安息香酸
（８２０ｍｇ，３．６ｍｍｏｌ）から、２，１５−ビス
（４−ベンジルオキシフェニルカルボキシ）−１，１，
１，１６，１６，１６−ヘキサフルオロヘキサデカン
（１．１ｇ，収率８５％、（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３
／１）を得た。 無色固体1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．１８〜１．４６（ｍ，
２０ Ｈ），１．８４（ｂｒｏａｄ ｑ．Ｊ＝７．３Ｈ
ｚ，４ Ｈ），５．１３（ｓ，４ Ｈ），５．５１（ｓｅ
ｘｔｅｔ，Ｊ＝６．７ Ｈｚ，２ Ｈ），７．０２（ｄ．
Ｊ＝９．０Ｈｚ，４Ｈ），７．３１〜７．４６（ｍ，１
０Ｈ），８．０２（ｄ．Ｊ＝９．０Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）２９３０，２８６０，１７３０，１６１
０，１５１０，１２６０，１１７０，１１００，１０１
０，７７０，７００ｃｍ-1 （３）１，１，１，１６，１６，１６−ヘキサフルオロ
−２，１５−ビス（４−ヒドロキシフェニルカルボキ
シ）ヘキサデカン[Chemical 50]2,10-bis (4-benzyloxyphenylcarboxy)
Si) -1,1,1,11,11,11-hexafluoro
Under the same conditions as the synthesis of undecane, 1,1,1,16,
16,16-Hexafluorohexadecane-2,15-
Diol (600 mg, 1.6 mmol, (S, S) /
(S, R) = 3/1), 4-benzyloxybenzoic acid
From (820 mg, 3.6 mmol), 2,15-bis
(4-benzyloxyphenylcarboxy) -1,1,
1,16,16,16-hexafluorohexadecane
(1.1 g, yield 85%, (S, S) / (S, R) = 3
/ 1) was obtained. Colorless solid1 1 H NMR (CDCl3) Δ 1.18 to 1.46 (m,
20 H), 1.84 (broad q.J = 7.3H)
z, 4 H), 5.13 (s, 4 H), 5.51 (se
xtet, J = 6.7 Hz, 2 H), 7.02 (d.
J = 9.0 Hz, 4H), 7.31 to 7.46 (m, 1
0H), 8.02 (d. J = 9.0Hz, 4H) IR (KBr) 2930, 2860, 1730, 161
0,1510,1260,1170,1100,101
0,770,700 cm-1 (3) 1,1,1,16,16,16-hexafluoro
-2,15-bis (4-hydroxyphenylcarboxy)
Si) Hexadecane
【化５１】 １，１，１，１１，１１，１１−ヘキサフルオロ−２，
１０−ビス（４−ヒドロキシフェニルカルボキシ）ウン
デカンの合成と同様な条件下、２，１５−ビス（４−ベ
ンジルオキシフェニルカルボキシ）−１，１，１，１
６，１６，１６−ヘキサフルオロヘキサデカン（９５０
ｍｇ，１．２１ｍｍｏｌ，（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３
／１）より、１，１，１，１６，１６，１６−ヘキサフ
ルオロ−２，１５−ビス（４−ヒドロキシフェニルカル
ボキシ）ヘキサデカン（７３４ｍｇ，収率１００％，
（Ｓ，Ｓ）／（Ｓ，Ｒ）＝３／１）を得た。さらに、高
速液体クロマトグラフィー（ダイセル社，ＣＨＩＲＡＬ
ＰＡＫ ＡＤ，ヘキサン／２−プロパノール＝６／１）
で（Ｓ，Ｓ）−１，１，１，１６，１６，１６−ヘキサ
フルオロ−２，１５−ビス（４−ヒドロキシフェニルカ
ルボキシ）ヘキサデカンを単離した。 無色油状物質1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ１．１５〜１．４５（ｍ，
２０ Ｈ），１．８６（ｂｒｏａｄ ｑ．Ｊ＝７．３Ｈ
ｚ，４ Ｈ），５．５１（ｓｅｘｔｅｔ，Ｊ＝６．７Ｈ
ｚ，２ Ｈ），６．１０（ｂｒｏａｄ ｓ，２Ｈ），６．
９０（ｄ．Ｊ＝８．８Ｈｚ，４ Ｈ），７．９９（ｄ．
Ｊ＝８．８Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）３４００，２９２０，２８５０，１７
００，１６０５，１５１０，１４４０，１２６０，１１
６５，１１００，８５０，７７０，７００ｃｍ-1 （４）（Ｓ，Ｓ）−１，１，１，１６，１６，１６−ヘ
キサフルオロ−２，１５−ビス［４−｛４−（４−オク
チルオキシフェニル）フェニルカルボキシ｝フェニルカ
ルボキシ］ヘキサデカン（式〔XIV〕の化合物）の合成[Chemical 51] 1,1,1,11,11,11-hexafluoro-2,
2,15-bis (4-benzyloxyphenylcarboxy) -1,1,1,1 under the same conditions as in the synthesis of 10-bis (4-hydroxyphenylcarboxy) undecane
6,16,16-hexafluorohexadecane (950
mg, 1.21 mmol, (S, S) / (S, R) = 3
/ 1,) 1,1,1,16,16,16-hexafluoro-2,15-bis (4-hydroxyphenylcarboxy) hexadecane (734 mg, yield 100%,
(S, S) / (S, R) = 3/1) was obtained. In addition, high performance liquid chromatography (Daicel, CHIRAL
PAK AD, hexane / 2-propanol = 6/1)
To isolate (S, S) -1,1,1,16,16,16-hexafluoro-2,15-bis (4-hydroxyphenylcarboxy) hexadecane. Colorless oily substance 1 H NMR (CDCl 3 ) δ1.15 to 1.45 (m,
20 H), 1.86 (broad q.J = 7.3H)
z, 4 H), 5.51 (sextet, J = 6.7H)
z, 2 H), 6.10 (broad s, 2 H), 6.
90 (d. J = 8.8 Hz, 4 H), 7.99 (d.
J = 8.8 Hz, 4 H) IR (neat) 3400, 2920, 2850, 17
00, 1605, 1510, 1440, 1260, 11
65,1100,850,770,700 cm -1 (4) (S, S) -1,1,1,16,16,16-hexafluoro-2,15-bis [4- {4- (4-octyl Synthesis of (oxyphenyl) phenylcarboxy} phenylcarboxy] hexadecane (compound of formula [XIV])
【化５２】 （Ｓ，Ｓ）−１，１，１，１１，１１，１１−ヘキサフ
ルオロ−２，１０−ビス［４−｛４−（４−オクチルオ
キシフェニル）フェニルカルボキシ｝フェニルカルボキ
シ］ウンデカンの合成と同様な条件下、（Ｓ，Ｓ）−
１，１，１，１６，１６，１６−ヘキサフルオロ−２，
１５−ビス（４−ヒドロキシフェニルカルボキシ）ヘキ
サデカン（１３４ｍｇ，０．２２ｍｍｏｌ）、４−（４
−オクチルオキシフェニル）安息香酸（１３９ｍｇ，
０．４３ｍｍｏｌ）、ＤＣＣ（１２９ｍｇ，０．６３ｍ
ｍｏｌ）、４−ジメチルアミノピリジン（２５ｍｇ，
０．２５ｍｍｏｌ）から、（Ｓ，Ｓ）−１，１，１，１
６，１６，１６−ヘキサフルオロ−２，１５−ビス［４
−｛４−（４−オクチルオキシフェニル）フェニルカル
ボキシ｝フェニルカルボキシ］ヘキサデカン（式〔XI
V〕の化合物）（２１１ｍｇ，収率７８％）を得た。 無色粉末 相転移温度Embedded image Similar to the synthesis of (S, S) -1,1,1,11,11,11-hexafluoro-2,10-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (S, S)-
1,1,1,16,16,16-hexafluoro-2,
15-bis (4-hydroxyphenylcarboxy) hexadecane (134 mg, 0.22 mmol), 4- (4
-Octyloxyphenyl) benzoic acid (139 mg,
0.43 mmol), DCC (129 mg, 0.63 m)
mol), 4-dimethylaminopyridine (25 mg,
0.25 mmol) to (S, S) -1,1,1,1
6,16,16-hexafluoro-2,15-bis [4
-{4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] hexadecane (formula [XI
Compound of V]) (211 mg, yield 78%) was obtained. Colorless powder phase transition temperature
【表１１８】 1Ｈ ＮＭＲ（ＣＤＣｌ3）δ０．９０（ｔ，Ｊ＝７．０
Ｈｚ，６ Ｈ），１．２０〜１．５３（ｍ，４０ Ｈ），
１．７８〜１．９３（ｍ，８ Ｈ），４．０２（ｔ，Ｊ
＝６．６ Ｈｚ，４ Ｈ），５．５６（ｓｉｘｔｅｔ，Ｊ
＝６．６ Ｈｚ，２ Ｈ），７．０１（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ），７．３６（ｄ，Ｊ＝８．８ Ｈｚ，４
Ｈ），７．６０（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），７．
７１（ｄ，Ｊ＝８．６ Ｈｚ，４ Ｈ），８．１７（ｄ，
Ｊ＝８．８ Ｈｚ，４ Ｈ），８．２３（ｄ，Ｊ＝８．６
Ｈｚ，４ Ｈ） ＩＲ（ＫＢｒ）２９３０，２８６０，１７３５，１６０
０，１２６０，１１８０，１１６０，１０７０，８３
０，７７０ｃｍ-1 （５）ラビング処理したポリイミド配向膜を透明電極基
板上に有するセル厚２μｍの液晶セルに（Ｓ，Ｓ）−
１，１，１，１６，１６，１６−ヘキサフルオロ−２，
１５−ビス［４−｛４−（４−オクチルオキシフェニ
ル）フェニルカルボキシ｝フェニルカルボキシ］ウンデ
カン（式〔XIV〕の化合物）を等方相において充填し、
液晶薄膜セルを作製した。１４０℃においてこの液晶セ
ルに４０Ｖｐｐ、０．１Ｈｚの三角波を印加したときの
透過光強度−印加電圧曲線は図６に示すように、ダブル
ヒステリシスを示すことにより反強誘電性液晶であるこ
とがわかる。[Table 118] 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 7.0)
Hz, 6 H), 1.20 to 1.53 (m, 40 H),
1.78 to 1.93 (m, 8 H), 4.02 (t, J
= 6.6 Hz, 4 H), 5.56 (sixtet, J
= 6.6 Hz, 2 H), 7.01 (d, J = 8.8)
Hz, 4 H), 7.36 (d, J = 8.8 Hz, 4
H), 7.60 (d, J = 8.8 Hz, 4 H), 7.
71 (d, J = 8.6 Hz, 4 H), 8.17 (d,
J = 8.8 Hz, 4 H), 8.23 (d, J = 8.6
Hz, 4 H) IR (KBr) 2930, 2860, 1735, 160
0, 1260, 1180, 1160, 1070, 83
0,770 cm -1 (5) A liquid crystal cell having a cell thickness of 2 μm, which has a rubbing-treated polyimide alignment film on a transparent electrode substrate (S, S)-
1,1,1,16,16,16-hexafluoro-2,
15-bis [4- {4- (4-octyloxyphenyl) phenylcarboxy} phenylcarboxy] undecane (compound of formula [XIV]) is packed in the isotropic phase,
A liquid crystal thin film cell was prepared. As shown in FIG. 6, the transmitted light intensity-applied voltage curve when a triangular wave of 40 Vpp and 0.1 Hz is applied to this liquid crystal cell at 140 ° C. shows double hysteresis, which indicates that the liquid crystal cell is an antiferroelectric liquid crystal. .
【０１７１】実施例６ （１）（Ｓ，Ｓ）−２，１３−テトラデカンジオールの
合成Example 6 (1) Synthesis of (S, S) -2,13-tetradecanediol
【化５３】 マグネシウム（４３０ｍｇ，１８ｍｍｏｌ）に１，８−
ジブロモオクタン（１．７ｇ，６．２ｍｍｏｌ）のＴＨ
Ｆ（８ｍｌ）溶液を滴下して、グリニャール反応剤を調
整した。これに、０℃でヨウ化銅（Ｉ）（１３０ｍｇ，
０．６８ｍｍｏｌ）をくわえ、さらに３０分かけて、
（Ｓ）−プロピレンオキシド（０．８５ｇ，１５ｍｍｏ
ｌ）を滴下した。室温で１０時間撹拌したのち、２Ｍ塩
酸で処理し、エーテル抽出、濃縮した。残渣をヘキサン
／酢酸エチル＝７／１混合溶媒で再結晶し、（Ｓ，Ｓ）
−２，１３−テトラデカンジオール（５９０ｍｇ，収率
４１％）を得た。また、ろ液を濃縮し、残渣をシリカゲ
ルカラムクロマトグラフィー（ヘキサン／酢酸エチル＝
３／１）で精製後、ヘキサン／酢酸エチル＝７／１混合
溶媒で再結晶し、（Ｓ，Ｓ）−２，１３−テトラデカン
ジオール（１８０ｍｇ，収率１３％）を得た。 無色針状晶 融点 ６１℃ ［α］D 20＋１０．０゜（ｃ＝１．０４，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．１９（ｄ，Ｊ＝６．
２ Ｈｚ，６ Ｈ），１．２５〜１．５０（ｍ，２２
Ｈ），３．７５〜３．８４（ｍ，２ Ｈ），ＩＲ（ＫＢ
ｒ）３３５０，２９２０，２８５０，１４７０，１３７
０，１１３０，１０４０，１０１５，９４５，７２０ｃ
ｍ-1 （２）（Ｓ，Ｓ）−２，１３−ビス（４−ベンジルオキ
シフェニルカルボキシ）テトラデカンの合成[Chemical 53]1,8- in magnesium (430 mg, 18 mmol)
TH of dibromooctane (1.7 g, 6.2 mmol)
F (8 ml) solution was added dropwise to prepare Grignard reactant.
Arranged To this, copper (I) iodide (130 mg,
0.68 mmol), and for another 30 minutes,
(S) -Propylene oxide (0.85 g, 15 mmo
l) was added dropwise. After stirring at room temperature for 10 hours, 2M salt
It was treated with acid, extracted with ether and concentrated. Hexane residue
/ Ethyl acetate = 7/1 recrystallized with a mixed solvent, (S, S)
-2,13-tetradecanediol (590 mg, yield
41%). The filtrate is concentrated and the residue is treated with silica gel.
Column chromatography (hexane / ethyl acetate =
After purification with 3/1), hexane / ethyl acetate = 7/1 mixture
Recrystallize in solvent to give (S, S) -2,13-tetradecane
A diol (180 mg, yield 13%) was obtained. Colorless needles melting point 61 ° C [α]D 20+ 10.0 ° (c = 1.04, CHCl3)1 1 H NMR (CDCl3) Δ 1.19 (d, J = 6.
2 Hz, 6 H), 1.25 to 1.50 (m, 22
H), 3.75 to 3.84 (m, 2 H), IR (KB
r) 3350, 2920, 2850, 1470, 137
0,1130,1040,1015,945,720c
m-1 (2) (S, S) -2,13-bis (4-benzyloxy)
Synthesis of (Ciphenylcarboxy) tetradecane
【化５４】 （Ｓ，Ｓ）−２，１３−テトラデカンジオール（４００
ｍｇ，１．５ｍｍｏｌ）、４−ベンジルオキシ安息香酸
（８００ｍｇ，３．５ｍｍｏｌ）、ＤＣＣ（８００ｍ
ｇ，３．９ｍｍｏｌ）、４−ジメチルアミノピリジン
（８０ｍｇ，０．６５ｍｍｏｌ）のジクロロメタン（２
０ｍｌ）溶液を室温で１日撹拌した。反応溶液をセライ
トろ過、濃縮後、残渣をシリカゲルカラムクロマトグラ
フィー（ヘキサン／酢酸エチル＝９／１）で精製し、
（Ｓ，Ｓ）−２，１３−ビス（４−ベンジルオキシフェ
ニルカルボキシ）テトラデカン（３８０ｍｇ，収率３９
％）を得た。 無色粘稠油状物質 ［α］D 20＋３２．９゜（ｃ＝１．０３，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．２０〜１．４５
（ｍ，１６ Ｈ），１．３１（ｄ，Ｊ＝６．３ Ｈｚ，６
Ｈ），１．５２〜１．６２（ｍ，２ Ｈ），１．６４〜
１．７４（ｍ，２ Ｈ），５．０７〜５．１５（ｍ，２
Ｈ），５．１２（ｓ，４ Ｈ），６．９９（ｄ，Ｊ＝
９．０ Ｈｚ，４ Ｈ），７．３０〜７．４５（ｍ，１０
Ｈ），７．９９（ｄ，Ｊ＝９．０ Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）２９３０，２８６０，１７１０，１６
００，１５１０，１４５０，１３８０，１２８０，１２
５０，１１６５，１１００，１０２０，１０００，８４
５，７７０，７００ｃｍ-1 （３）（Ｓ，Ｓ）−２，１３−ビス（４−ヒドロキシフ
ェニルカルボキシ）テトラデカンの合成[Chemical 54](S, S) -2,13-tetradecanediol (400
mg, 1.5 mmol), 4-benzyloxybenzoic acid
(800 mg, 3.5 mmol), DCC (800 m
g, 3.9 mmol), 4-dimethylaminopyridine
(80 mg, 0.65 mmol) of dichloromethane (2
0 ml) solution was stirred at room temperature for 1 day. Reaction solution
After filtration and concentration, the residue is purified by silica gel column chromatography.
Purification with hexane (hexane / ethyl acetate = 9/1),
(S, S) -2,13-Bis (4-benzyloxyphene)
Nylcarboxy) tetradecane (380 mg, yield 39)
%). Colorless viscous oily substance [α]D 20+ 32.9 ° (c = 1.03, CHCl 33)1 1 H NMR (CDCl3) Δ 1.20 to 1.45
(M, 16 H), 1.31 (d, J = 6.3 Hz, 6
H), 1.52 to 1.62 (m, 2 H), 1.64 to
1.74 (m, 2 H), 5.07 to 5.15 (m, 2
H), 5.12 (s, 4 H), 6.99 (d, J =
9.0 Hz, 4 H), 7.30 to 7.45 (m, 10
H), 7.99 (d, J = 9.0 Hz, 4 H) IR (neat) 2930, 2860, 1710, 16
00, 1510, 1450, 1380, 1280, 12
50, 1165, 1100, 1020, 1000, 84
5,770,700 cm-1 (3) (S, S) -2,13-bis (4-hydroxyphenyl)
Synthesis of (phenylcarboxy) tetradecane
【化５５】 （Ｓ，Ｓ）−２，１３−ビス（４−ベンジルオキシフェ
ニルカルボキシ）テトラデカン（３８０ｍｇ，０．５８
ｍｍｏｌ）、１０％パラジウム−炭素（５０ｍｇ）の酢
酸エチル（１５ｍｌ）懸濁液を水素雰囲気下、室温で５
時間撹拌した。反応液をセライトろ過後、濃縮し、残渣
をシカリゲルカラムクロマトグラフィー（ヘキサン／酢
酸エチル＝３／１）で精製し、（Ｓ，Ｓ）−２，１３−
ビス（４−ヒドロキシフェニルカルボキシ）テトラデカ
ン（２３０ｍｇ，収率８４％）を得た。 無色粘稠油状物質 ［α］D 20＋２２．２゜（ｃ＝０．９９，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．１６〜１．４１
（ｍ，１６ Ｈ），１．３２（ｄ，Ｊ＝６．３ Ｈｚ，６
Ｈ），１．５３〜１．６３（ｍ，２ Ｈ），１．６５〜
１．７５（ｍ，２ Ｈ），５．０９〜５．１９（ｍ，２
Ｈ），６．１〜７．１（ｂｒｏａｄ，２ Ｈ），６．８
８（ｄ，Ｊ＝８．９ Ｈｚ，４ Ｈ），７．９４（ｄ，Ｊ
＝８．９ Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）３３５０，２９２０，２８５０，１６
８０，１６０５，１５９０，１５１０，１４４０，１３
５５，１３１０，１２８０，１２３０，１１６０，１１
１０，８５０，７７０，７００，６２０ｃｍ-1 （４）（Ｓ，Ｓ）−２，１３−ビス｛４−［４−（４−
オクチルオキシフェニル）フェニルカルボキシ］フェニ
ルカルボキシ｝テトラデカンの合成[Chemical 55](S, S) -2,13-Bis (4-benzyloxyphene)
Nylcarboxy) tetradecane (380 mg, 0.58
mmol), 10% palladium-carbon (50 mg) vinegar
A suspension of ethyl acidate (15 ml) under hydrogen atmosphere at room temperature
Stirred for hours. The reaction mixture was filtered through Celite and then concentrated to give a residue.
Column chromatography (hexane / vinegar)
Ethylate = 3/1) and purified (S, S) -2,13-
Bis (4-hydroxyphenylcarboxy) tetradeca
(230 mg, 84% yield) was obtained. Colorless viscous oily substance [α]D 20+ 22.2 ° (c = 0.99, CHCl3)1 1 H NMR (CDCl3) Δ 1.16 to 1.41
(M, 16 H), 1.32 (d, J = 6.3 Hz, 6
H), 1.53 to 1.63 (m, 2 H), 1.65
1.75 (m, 2 H), 5.09 to 5.19 (m, 2
H), 6.1-7.1 (broad, 2 H), 6.8.
8 (d, J = 8.9 Hz, 4 H), 7.94 (d, J
= 8.9 Hz, 4 H) IR (neat) 3350, 2920, 2850, 16
80, 1605, 1590, 1510, 1440, 13
55, 1310, 1280, 1230, 1160, 11
10,850,770,700,620cm-1 (4) (S, S) -2,13-bis {4- [4- (4-
Octyloxyphenyl) phenylcarboxy] phenyl
Synthesis of lecarboxy} tetradecane
【化５６】 （Ｓ，Ｓ）−２，１３−ビス（４−ヒドロキシフェニル
カルボキシ）テトラデカン（２３０ｍｇ，０．４９ｍｍ
ｏｌ）、４−（４−オクチルオキシフェニル）安息香酸
（３５０ｍｇ，１．１ｍｍｏｌ）、ＤＣＣ（２４５ｍ
ｇ，１．２ｍｍｏｌ）、４−ジメチルアミノピリジン
（１０ｍｇ，０．０８ｍｍｏｌ）のジクロロメタン（１
０ｍｌ）溶液を室温で１日撹拌した。反応溶液をセライ
トろ過、濃縮後、残渣をシリカゲルカラムクロマトグラ
フィー（ジクロロメタン）で精製し、さらに再結晶（ヘ
キサン／ジクロロメタン＝５／１）して、（Ｓ，Ｓ）−
２，１３−ビス｛４−［４−（４−オクチルオキシフェ
ニル）フェニルカルボキシ］フェニルカルボキシ｝テト
ラデカン（４５０ｍｇ，収率８５％）を得た。無色粉末
相転移温度を下表１１９に示す。[Chemical 56] (S, S) -2,13-Bis (4-hydroxyphenylcarboxy) tetradecane (230 mg, 0.49 mm
ol), 4- (4-octyloxyphenyl) benzoic acid (350 mg, 1.1 mmol), DCC (245 m
g, 1.2 mmol), 4-dimethylaminopyridine (10 mg, 0.08 mmol) in dichloromethane (1
0 ml) solution was stirred at room temperature for 1 day. The reaction solution was filtered through Celite and concentrated, and the residue was purified by silica gel column chromatography (dichloromethane) and further recrystallized (hexane / dichloromethane = 5/1) to give (S, S)-
2,13-bis {4- [4- (4-octyloxyphenyl) phenylcarboxy] phenylcarboxy} tetradecane (450 mg, yield 85%) was obtained. Colorless powder The phase transition temperatures are shown in Table 119 below.
【表１１９】 ［α］D 20＋２２．９゜（ｃ＝１．０２，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ ０．９０（ｔ，Ｊ＝６．
９ Ｈｚ，６ Ｈ），１．２４〜１．５２（ｍ，３６
Ｈ），１．３４（ｄ，Ｊ＝６．３ Ｈｚ，６ Ｈ），１．
５６〜１．６６（ｍ，２ Ｈ），１．６８〜１．７６
（ｍ，２ Ｈ），１．８２（ｂｒｏａｄ ｑｕｉｎｔｅ
ｔ，Ｊ＝６．６ Ｈｚ，４ Ｈ），４．０２（ｔ，Ｊ＝
６．６ Ｈｚ，４ Ｈ），５．１６（ｂｒｏａｄ ｓｅｘ
ｔｅｔ，Ｊ＝６．３ Ｈｚ，２ Ｈ），７．０１（ｄ，Ｊ
＝８．７ Ｈｚ，４ Ｈ），７．３１（ｄ，Ｊ＝８．７
Ｈｚ，４ Ｈ），７．５９（ｄ，Ｊ＝８．７ Ｈｚ，４
Ｈ），７．７０（ｄ，Ｊ＝８．５ Ｈｚ，４ Ｈ），８．
１３（ｄ，Ｊ＝８．７ Ｈｚ，４ Ｈ），８．２３（ｄ，
Ｊ＝８．５ Ｈｚ，４ Ｈ），ＩＲ（ＫＢｒ）２９２０，
２８５０，１７３０，１７２０，１６００，１５００，
１２７０，１２００，１１６０，１１１５，１０７０，
１０１０，８３０，７７０，６９０ｃｍ-1 （５）（Ｓ，Ｓ）−２，１３−ビス｛４−［４−（４−
オクチルオキシフェニル）フェニルカルボキシ］フェニ
ルカルボキシ｝テトラデカンの電気光学特性 ラビングしたポリイミド配向膜を透明電極基板上に有す
るセル厚２μｍの液晶セルに（Ｓ，Ｓ）−２，１３−ビ
ス｛４−［４−（４−オクチルオキシフェニル）フェニ
ルカルボキシ］フェニルカルボキシ｝テトラデカンを等
方相において充填し、液晶薄膜セルを作製した。液晶セ
ルに、４０Ｖｐｐ、１Ｈｚの三角波を印加したときの透
過光強度−印加電圧曲線は図７に示すようになる。
（ａ）、（ｂ）、（ｃ）は各々１５０℃、１４０℃、１
３０℃において測定したものである。[Table 119] [Α] D 20 + 22.9 ° (c = 1.02, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 6.
9 Hz, 6 H), 1.24 to 1.52 (m, 36
H), 1.34 (d, J = 6.3 Hz, 6 H), 1.
56-1.66 (m, 2H), 1.68-1.76
(M, 2 H), 1.82 (broad quinte
t, J = 6.6 Hz, 4 H), 4.02 (t, J =
6.6 Hz, 4 H), 5.16 (broad sex
tet, J = 6.3 Hz, 2 H), 7.01 (d, J
= 8.7 Hz, 4 H), 7.31 (d, J = 8.7)
Hz, 4 H), 7.59 (d, J = 8.7 Hz, 4
H), 7.70 (d, J = 8.5 Hz, 4 H), 8.
13 (d, J = 8.7 Hz, 4 H), 8.23 (d,
J = 8.5 Hz, 4 H), IR (KBr) 2920,
2850, 1730, 1720, 1600, 1500,
1270, 1200, 1160, 1115, 1070,
1010,830,770,690 cm -1 (5) (S, S) -2,13-bis {4- [4- (4-
Electro-Optical Properties of Octyloxyphenyl) phenylcarboxy] phenylcarboxy} tetradecane A (S, S) -2,13-bis {4- [4 [4 [4 A liquid crystal thin film cell was prepared by filling-(4-octyloxyphenyl) phenylcarboxy] phenylcarboxy} tetradecane in the isotropic phase. A transmitted light intensity-applied voltage curve when a triangular wave of 40 Vpp and 1 Hz is applied to the liquid crystal cell is as shown in FIG.
(A), (b), (c) are 150 ℃, 140 ℃, 1
It is measured at 30 ° C.
【０１７２】実施例７ （１）（Ｓ，Ｓ）−２，１４−ペンタデカンジオールの
合成Example 7 (1) Synthesis of (S, S) -2,14-pentadecanediol
【化５７】 （Ｓ，Ｓ）−２，１３−テトラデカンジオールの合成と
同様な条件下、１，９−ジブロモノナン（２．１ｇ，
７．３ｍｍｏｌ）、（Ｓ）−プロピレンオキシド（１．
０ｇ，１５ｍｍｏｌ）より、（Ｓ，Ｓ）−２，１４−ペ
ンタデカンジオール（１．０７ｇ，収率６０％）を得
た。 無色板状晶 融点 ７１−７４℃ ［α］D 20＋７．１゜（ｃ＝１．０３，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．１９（ｄ，Ｊ＝６．
２ Ｈｚ，６ Ｈ），１．２５〜１．５０（ｍ，２４
Ｈ），３．７４〜３．８３（ｍ，２ Ｈ），ＩＲ（ＫＢ
ｒ）３３００，２９２０，２８５０，１４７０，１３７
０，１３２０，１１３０，１０７０，９３０，８４０，
７２０ｃｍ-1 （２）（Ｓ，Ｓ）−２，１４−ビス（４−ベンジルオキ
シフェニルカルボキシ）ペンタデカンの合成[Chemical 57]Synthesis of (S, S) -2,13-tetradecanediol and
Under similar conditions, 1,9-dibromononane (2.1 g,
7.3 mmol), (S) -propylene oxide (1.
0 g, 15 mmol), (S, S) -2,14-pe
Nantadecanediol (1.07 g, yield 60%) was obtained.
Was. Colorless plate crystal melting point 71-74 ° C [α]D 20+ 7.1 ° (c = 1.03, CHCl3)1 1 H NMR (CDCl3) Δ 1.19 (d, J = 6.
2 Hz, 6 H), 1.25 to 1.50 (m, 24
H), 3.74 to 3.83 (m, 2 H), IR (KB
r) 3300, 2920, 2850, 1470, 137
0, 1320, 1130, 1070, 930, 840,
720 cm-1 (2) (S, S) -2,14-bis (4-benzyloxy)
Synthesis of (Ciphenylcarboxy) pentadecane
【化５８】 （Ｓ，Ｓ）−２，１３−ビス（４−ベンジルオキシフェ
ニルカルボキシ）テトラデカンの合成と同様な条件下、
（Ｓ，Ｓ）−２，１４−ペンタデカンジオール（１５０
ｍｇ，０．６１ｍｍｏｌ）、４−ベンジルオキシ安息香
酸（３０５ｍｇ，１．３ｍｍｏｌ）より、（Ｓ，Ｓ）−
２，１４−ビス（４−ベンジルオキシフェニルカルボキ
シ）ペンタデカン（２９６ｍｇ，収率７３％）を得た。 無色粘稠油状物質 ［α］D 20＋２５．４゜（ｃ＝１．０１，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．２０〜１．４４
（ｍ，１８ Ｈ），１．３１（ｄ，Ｊ＝６．３ Ｈｚ，６
Ｈ），１．５２〜１．６２（ｍ，２ Ｈ），１．６５〜
１．７５（ｍ，２ Ｈ），５．０６〜５．１８（ｍ，２
Ｈ），５．１１（ｓ，４ Ｈ），６．９８（ｄ，Ｊ＝
９．０ Ｈｚ，４ Ｈ），７．３１〜７．４５（ｍ，１０
Ｈ），７．９９（ｄ，Ｊ＝９．０ Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）２９２０，２８５０，１７０５，１６
００，１５０５，１４５０，１３８０，１３１０，１２
７０，１２５０，１１６５，１１００，１０２０，１０
０５，８４５，７７０，７３０，６９５ｃｍ-1 （３）（Ｓ，Ｓ）−２，１４−ビス（４−ヒドロキシフ
ェニルカルボキシ）ペンタデカンの合成Embedded image Under the same conditions as in the synthesis of (S, S) -2,13-bis (4-benzyloxyphenylcarboxy) tetradecane,
(S, S) -2,14-Pentadecanediol (150
mg, 0.61 mmol), 4-benzyloxybenzoic acid (305 mg, 1.3 mmol), and then (S, S)-
2,14-bis (4-benzyloxyphenylcarboxy) pentadecane (296 mg, yield 73%) was obtained. Colorless viscous oily substance [α] D 20 + 25.4 ° (c = 1.01, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 1.20 to 1.44
(M, 18 H), 1.31 (d, J = 6.3 Hz, 6
H), 1.52 to 1.62 (m, 2 H), 1.65
1.75 (m, 2 H), 5.06 to 5.18 (m, 2
H), 5.11 (s, 4 H), 6.98 (d, J =
9.0 Hz, 4 H), 7.31 to 7.45 (m, 10
H), 7.99 (d, J = 9.0 Hz, 4 H) IR (neat) 2920, 2850, 1705, 16
00, 1505, 1450, 1380, 1310, 12
70, 1250, 1165, 1100, 1020, 10
05,845,770,730,695 cm −1 (3) (S, S) -2,14-Bis (4-hydroxyphenylcarboxy) pentadecane
【化５９】 （Ｓ，Ｓ）−２，１３−ビス（４−ヒドロキシフェニル
カルボキシ）テトラデカンの合成と同様な条件下、
（Ｓ，Ｓ）−２，１４−ビス（４−ベンジルオキシフェ
ニルカルボキシ）ペンタデカン（５００ｍｇ，０．７５
ｍｍｏｌ）より、（Ｓ，Ｓ）−２，１４−ビス（４−ヒ
ドロキシフェニルカルボキシ）ペンタデカン（３２４ｍ
ｇ，収率８９％）を得た。 無色粘稠油状物質 ［α］D 20＋２７．３゜（ｃ＝１．０２，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．１６〜１．４４
（ｍ，１８ Ｈ），１．３２（ｄ，Ｊ＝６．３ Ｈｚ，６
Ｈ），１．５３〜１．６３（ｍ，２ Ｈ），１．６６〜
１．７６（ｍ，２ Ｈ），５．０９〜５．１９（ｍ，２
Ｈ），６．３〜７．２（ｂｒｏａｄ，２ Ｈ），６．８
８（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），７．９４（ｄ，Ｊ
＝８．８ Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）３３５０，２９２０，２８５０，１６
７０，１６００，１５９０，１５１０，１４４０，１３
５５，１２８０，１１６０，１１２０，８５０，７７
０，７００，６２０ｃｍ-1 （４）（Ｓ，Ｓ）−２，１４−ビス｛４−［４−（４−
オクチルオキシフェニル）フェニルカルボキシ］フェニ
ルカルボキシ｝ペンタデカンの合成Embedded image Under the same conditions as in the synthesis of (S, S) -2,13-bis (4-hydroxyphenylcarboxy) tetradecane,
(S, S) -2,14-Bis (4-benzyloxyphenylcarboxy) pentadecane (500 mg, 0.75
mmol), (S, S) -2,14-bis (4-hydroxyphenylcarboxy) pentadecane (324 m
g, yield 89%). Colorless viscous oily substance [α] D 20 + 27.3 ° (c = 1.02, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 1.16 to 1.44
(M, 18 H), 1.32 (d, J = 6.3 Hz, 6
H), 1.53 to 1.63 (m, 2 H), 1.66 to
1.76 (m, 2 H), 5.09 to 5.19 (m, 2
H), 6.3-7.2 (broad, 2 H), 6.8.
8 (d, J = 8.8 Hz, 4 H), 7.94 (d, J
= 8.8 Hz, 4 H) IR (neat) 3350, 2920, 2850, 16
70, 1600, 1590, 1510, 1440, 13
55, 1280, 1160, 1120, 850, 77
0,700,620 cm -1 (4) (S, S) -2,14-bis {4- [4- (4-
Synthesis of octyloxyphenyl) phenylcarboxy] phenylcarboxy} pentadecane
【化６０】 （Ｓ，Ｓ）−２，１３−ビス｛４−［４−（４−オクチ
ルオキシフェニル）フェニルカルボキシ］フェニルカル
ボキシ｝テトラデカンの合成と同様な条件下、（Ｓ，
Ｓ）−２，１４−ビス（４−ヒドロキシフェニルカルボ
キシ）ペンタデカン（２４０ｍｇ，０．５０ｍｍｏ
ｌ）、４−（４−オクチルオキシフェニル）安息香酸
（３４０ｍｇ，１．０４ｍｍｏｌ）より、（Ｓ，Ｓ）−
２，１４−ビス｛４−［４−（４−オクチルオキシフェ
ニル）フェニルカルボキシ］フェニルカルボキシ｝ペン
タデカン（４４０ｍｇ，収率８１％）を得た。無色粉末
相転移温度を下表１２０に示す。Embedded image Under the same conditions as in the synthesis of (S, S) -2,13-bis {4- [4- (4-octyloxyphenyl) phenylcarboxy] phenylcarboxy} tetradecane, (S, S)
S) -2,14-Bis (4-hydroxyphenylcarboxy) pentadecane (240 mg, 0.50 mmo
l), 4- (4-octyloxyphenyl) benzoic acid (340 mg, 1.04 mmol), from (S, S)-
2,14-bis {4- [4- (4-octyloxyphenyl) phenylcarboxy] phenylcarboxy} pentadecane (440 mg, yield 81%) was obtained. Colorless powder The phase transition temperatures are shown in Table 120 below.
【表１２０】 ［α］D 20＋２１．８゜（ｃ＝１．０５，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ ０．９０（ｔ，Ｊ＝７．
０ Ｈｚ，６ Ｈ），１．２４〜１．５２（ｍ，３８
Ｈ），１．３４（ｄ，Ｊ＝６．２ Ｈｚ，６ Ｈ），１．
５６〜１．６６（ｍ，２ Ｈ），１．６８〜１．７６
（ｍ，２ Ｈ），１．８２（ｂｒｏａｄ ｑｕｉｎｔｅ
ｔ，Ｊ＝６．６ Ｈｚ，４ Ｈ），４．０２（ｔ，Ｊ＝
６．６ Ｈｚ，４ Ｈ），５．１６（ｂｒｏａｄ ｓｅｘ
ｔｅｔ，Ｊ＝６．２ Ｈｚ，２ Ｈ），７．０１（ｄ，Ｊ
＝８．８ Ｈｚ，４ Ｈ），７．３１（ｄ，Ｊ＝８．８
Ｈｚ，４ Ｈ），７．５９（ｄ，Ｊ＝８．８ Ｈｚ，４
Ｈ），７．７０（ｄ，Ｊ＝８．６ Ｈｚ，４ Ｈ），８．
１３（ｄ，Ｊ＝８．８ Ｈｚ，４ Ｈ），８．２３（ｄ，
Ｊ＝８．６ Ｈｚ，４ Ｈ），ＩＲ（ＫＢｒ）２９００，
２８５０，１７３０，１７１０，１６００，１２６０，
１１９０，１１６０，１１１０，１０７０，１０１０，
８３０，７６０ｃｍ-1 [Table 120] [Α] D 20 + 21.8 ° (c = 1.05, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 7.
0 Hz, 6 H), 1.24 to 1.52 (m, 38
H), 1.34 (d, J = 6.2 Hz, 6 H), 1.
56-1.66 (m, 2H), 1.68-1.76
(M, 2 H), 1.82 (broad quinte
t, J = 6.6 Hz, 4 H), 4.02 (t, J =
6.6 Hz, 4 H), 5.16 (broad sex
tet, J = 6.2 Hz, 2 H), 7.01 (d, J
= 8.8 Hz, 4 H), 7.31 (d, J = 8.8)
Hz, 4 H), 7.59 (d, J = 8.8 Hz, 4
H), 7.70 (d, J = 8.6 Hz, 4 H), 8.
13 (d, J = 8.8 Hz, 4 H), 8.23 (d,
J = 8.6 Hz, 4 H), IR (KBr) 2900,
2850, 1730, 1710, 1600, 1260,
1190, 1160, 1110, 1070, 1010,
830,760 cm -1
【０１７３】実施例８ （１）（Ｓ，Ｓ）−２，１５−ヘキサデカンジオールの
合成Example 8 (1) Synthesis of (S, S) -2,15-hexadecanediol
【化６１】 （Ｓ，Ｓ）−２，１３−テトラデカンジオールの合成と
同様な条件下、１，９−ジブロモデカン（１．８ｇ，
６．０ｍｍｏｌ）、（Ｓ）−プロピレンオキシド（０．
８５ｇ，１７ｍｍｏｌ）より、（Ｓ，Ｓ）−２，１４−
ヘキサデカンジオール（１．０１ｇ，収率６６％）を得
た。 無色板状晶 融点 ６９℃ ［α］D 20＋９．０゜（ｃ＝１．０２，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．１９（ｄ，Ｊ＝６．
２ Ｈｚ，６ Ｈ），１．２４〜１．５０（ｍ，２６
Ｈ），３．７５〜３．８４（ｍ，２ Ｈ），ＩＲ（ＫＢ
ｒ）３４００，２９２０，２８５０，１４６０，１３７
０，１１３０，１１１０，１０４５，１０３０，９９
５，９４０，８４０，７３０ｃｍ-1 （２）（Ｓ，Ｓ）−２，１５−ビス（４−ベンジルオキ
シフェニルカルボキシ）ヘキサデカンの合成[Chemical formula 61]Synthesis of (S, S) -2,13-tetradecanediol and
Under similar conditions, 1,9-dibromodecane (1.8 g,
6.0 mmol), (S) -propylene oxide (0.
85 g, 17 mmol), (S, S) -2,14-
Hexadecanediol (1.01 g, yield 66%) was obtained.
Was. Colorless plate, melting point 69 ° C [α]D 20+ 9.0 ° (c = 1.02, CHCl3)1 1 H NMR (CDCl3) Δ 1.19 (d, J = 6.
2 Hz, 6 H), 1.24 to 1.50 (m, 26
H), 3.75 to 3.84 (m, 2 H), IR (KB
r) 3400, 2920, 2850, 1460, 137
0,1130,1110,1045,1030,99
5,940,840,730cm-1 (2) (S, S) -2,15-bis (4-benzyloxy)
Synthesis of (Ciphenylcarboxy) hexadecane
【化６２】 （Ｓ，Ｓ）−２，１３−ビス（４−ベンジルオキシフェ
ニルカルボキシ）テトラデカンの合成と同様な条件下、
（Ｓ，Ｓ）−２，１５−ヘキサデカンジオール（４００
ｍｇ，１．６ｍｍｏｌ）、４−ベンジルオキシ安息香酸
（７８０ｍｇ，３．４ｍｍｏｌ）より、（Ｓ，Ｓ）−
２，１５−ビス（４−ベンジルオキシフェニルカルボキ
シ）ヘキサデカン（１．０ｇ，収率９４％）を得た。 無色粘稠油状物質 ［α］D 20＋３１．３゜（ｃ＝１．０２，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．２０〜１．４４
（ｍ，２０ Ｈ），１．３１（ｄ，Ｊ＝６．２ Ｈｚ，６
Ｈ），１．５３〜１．６３（ｍ，２ Ｈ），１．６５〜
１．７５（ｍ，２ Ｈ），５．０６〜５．１８（ｍ，２
Ｈ），５．１１（ｓ，４ Ｈ），６．９８（ｄ，Ｊ＝
８．９ Ｈｚ，４ Ｈ），７．３０〜７．４５（ｍ，１０
Ｈ），７．９９（ｄ，Ｊ＝８．９ Ｈｚ，４ Ｈ） ＩＲ（ｎｅａｔ）２９２０，２８５０，１７００，１６
００，１５０５，１４５０，１３８０，１２７０，１２
４５，１１６５，１１００，１０２０，１０００，８４
５，７７０，７３０，７００ｃｍ-1 （３）（Ｓ，Ｓ）−２，１５−ビス（４−ヒドロキシフ
ェニルカルボキシ）ヘキサデカンの合成[Chemical formula 62](S, S) -2,13-Bis (4-benzyloxyphene)
Conditions similar to the synthesis of (nylcarboxy) tetradecane,
(S, S) -2,15-hexadecanediol (400
mg, 1.6 mmol), 4-benzyloxybenzoic acid
From (780 mg, 3.4 mmol), (S, S)-
2,15-bis (4-benzyloxyphenylcarboxy)
Si) Hexadecane (1.0 g, yield 94%) was obtained. Colorless viscous oily substance [α]D 20+ 31.3 ° (c = 1.02, CHCl3)1 1 H NMR (CDCl3) Δ 1.20 to 1.44
(M, 20 H), 1.31 (d, J = 6.2 Hz, 6
H), 1.53 to 1.63 (m, 2 H), 1.65
1.75 (m, 2 H), 5.06 to 5.18 (m, 2
H), 5.11 (s, 4 H), 6.98 (d, J =
8.9 Hz, 4 H), 7.30 to 7.45 (m, 10
H), 7.99 (d, J = 8.9 Hz, 4 H) IR (neat) 2920, 2850, 1700, 16
00, 1505, 1450, 1380, 1270, 12
45, 1165, 1100, 1020, 1000, 84
5,770,730,700cm-1 (3) (S, S) -2,15-bis (4-hydroxyphenyl)
Synthesis of (phenylcarboxy) hexadecane
【化６３】 （Ｓ，Ｓ）−２，１３−ビス（４−ヒドロキシフェニル
カルボキシ）テトラデカンの合成と同様な条件下、
（Ｓ，Ｓ）−２，１５−ビス（４−ベンジルオキシフェ
ニルカルボキシ）ヘキサデカン（９００ｍｇ，１．３ｍ
ｍｏｌ）より、（Ｓ，Ｓ）−２，１４−ビス（４−ヒド
ロキシフェニルカルボキシ）ヘキサデカン（５６０ｍ
ｇ，収率８５％）を得た。 無色粉末 融点 ８３−８５℃ ［α］D 20＋３０．５゜（ｃ＝１．０４，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ １．１６〜１．４２
（ｍ，２０ Ｈ），１．３２（ｄ，Ｊ＝６．３ Ｈｚ，６
Ｈ），１．５３〜１．６３（ｍ，２ Ｈ），１．６６〜
１．７６（ｍ，２ Ｈ），３．０〜６．０（ｂｒｏａ
ｄ，２ Ｈ），５．０９〜５．１８（ｍ，２ Ｈ），６．
８８（ｄ，Ｊ＝８．９ Ｈｚ，４ Ｈ），７．９５（ｄ，
Ｊ＝８．９ Ｈｚ） ＩＲ（ＫＢｒ）３４００，２９２０，２８５０，１６８
０，１６０５，１５９０，１５１０，１４５０，１３６
０，１２８０，１１６５，１１２０，８６０，７７５，
７００，６１０ｃｍ-1 （４）（Ｓ，Ｓ）−２，１５−ビス｛４−［４−（４−
オクチルオキシフェニル）フェニルカルボキシ］フェニ
ルカルボキシ｝ヘキサデカンの合成[Chemical formula 63](S, S) -2,13-bis (4-hydroxyphenyl)
Conditions similar to the synthesis of (carboxy) tetradecane,
(S, S) -2,15-bis (4-benzyloxyphene
Nylcarboxy) hexadecane (900mg, 1.3m
mol) from (S, S) -2,14-bis (4-hydr)
Roxyphenylcarboxy) hexadecane (560m
g, yield 85%) was obtained. Colorless powder, melting point 83-85 ° C [α]D 20+ 30.5 ° (c = 1.04, CHCl3)1 1 H NMR (CDCl3) Δ 1.16 to 1.42
(M, 20 H), 1.32 (d, J = 6.3 Hz, 6
H), 1.53 to 1.63 (m, 2 H), 1.66 to
1.76 (m, 2 H), 3.0 to 6.0 (broa
d, 2 H), 5.09 to 5.18 (m, 2 H), 6.
88 (d, J = 8.9 Hz, 4 H), 7.95 (d,
J = 8.9 Hz) IR (KBr) 3400, 2920, 2850, 168
0,1605,1590,1510,1450,136
0,1280,1165,1120,860,775,
700,610cm-1 (4) (S, S) -2,15-bis {4- [4- (4-
Octyloxyphenyl) phenylcarboxy] phenyl
Synthesis of lucarboxy} hexadecane
【化６４】 （Ｓ，Ｓ）−２，１３−ビス｛４−［４−（４−オクチ
ルオキシフェニル）フェニルカルボキシ］フェニルカル
ボキシ｝テトラデカンの合成と同様な条件下、（Ｓ，
Ｓ）−２，１５−ビス（４−ヒドロキシフェニルカルボ
キシ）ヘキサデカン（２３５ｍｇ，０．４７ｍｍｏ
ｌ）、４−（４−オクチルオキシフェニル）安息香酸
（３２５ｍｇ，１．０ｍｍｏｌ）より、（Ｓ，Ｓ）−
２，１５−ビス｛４−［４−（４−オクチルオキシフェ
ニル）フェニルカルボキシ］フェニルカルボキシ｝ヘキ
サデカン（３９０ｍｇ，収率７４％）を得た。 無色粉末 相転移温度を下表１２１に示す。[Chemical 64] Under the same conditions as in the synthesis of (S, S) -2,13-bis {4- [4- (4-octyloxyphenyl) phenylcarboxy] phenylcarboxy} tetradecane, (S, S)
S) -2,15-Bis (4-hydroxyphenylcarboxy) hexadecane (235 mg, 0.47 mmo
l), 4- (4-octyloxyphenyl) benzoic acid (325 mg, 1.0 mmol), and then (S, S)-
2,15-Bis {4- [4- (4-octyloxyphenyl) phenylcarboxy] phenylcarboxy} hexadecane (390 mg, yield 74%) was obtained. Colorless powder The phase transition temperatures are shown in Table 121 below.
【表１２１】 ［α］D 20＋２２．９゜（ｃ＝１．０１，ＣＨＣｌ3）1 Ｈ ＮＭＲ（ＣＤＣｌ3）δ ０．９０（ｔ，Ｊ＝７．
０ Ｈｚ，６ Ｈ），１．２４〜１．５２（ｍ，４０
Ｈ），１．３４（ｄ，Ｊ＝６．２ Ｈｚ，６ Ｈ），１．
５６〜１．６６（ｍ，２ Ｈ），１．６８〜１．７６
（ｍ，２ Ｈ），１．８２（ｂｒｏａｄ ｑｕｉｎｔｅ
ｔ，Ｊ＝６．６ Ｈｚ，４ Ｈ），４．０２（ｔ，Ｊ＝
６．６ Ｈｚ，４ Ｈ），５．１６（ｂｒｏａｄ ｓｅｘ
ｔｅｔ，Ｊ＝６．２ Ｈｚ，２ Ｈ），７．０１（ｄ，Ｊ
＝８．８ Ｈｚ，４ Ｈ），７．３１（ｄ，Ｊ＝８．７
Ｈｚ，４ Ｈ），７．５９（ｄ，Ｊ＝８．８ Ｈｚ，４
Ｈ），７．７０（ｄ，Ｊ＝８．５ Ｈｚ，４ Ｈ），８．
１３（ｄ，Ｊ＝８．７ Ｈｚ，４ Ｈ），８．２３（ｄ，
Ｊ＝８．５ Ｈｚ，４ Ｈ），ＩＲ（ＫＢｒ）２９００，
２８５０，１７３０，１７１５，１６００，１５００，
１４６５，１２６５，１２００，１１６０，１１１０，
１０７０，１０１０，８３０，７６０，６９０ｃｍ-1 （５）（Ｓ，Ｓ）−２，１５−ビス｛４−［４−（４−
オクチルオキシフェニル）フェニルカルボキシ］フェニ
ルカルボキシ｝ヘキサデカンの電気光学特性 ラビングしたポリイミド配向膜を透明電極基板上に有す
るセル厚２μｍの液晶セルに（Ｓ，Ｓ）−２，１５−ビ
ス｛４−［４−（４−オクチルオキシフェニル）フェニ
ルカルボキシ］フェニルカルボキシ｝ヘキサデカンを等
方相において充填し、液晶薄膜セルを作製した。液晶セ
ルに、４０Ｖｐｐ、１Ｈｚの三角波を印加したときの透
過光強度−印加電圧曲線は図８に示すようになる。
（ａ）、（ｂ）は各々１４０℃、１３０℃において測定
したものである。[Table 121] [Α] D 20 + 22.9 ° (c = 1.01, CHCl 3 ) 1 H NMR (CDCl 3 ) δ 0.90 (t, J = 7.
0 Hz, 6 H), 1.24 to 1.52 (m, 40
H), 1.34 (d, J = 6.2 Hz, 6 H), 1.
56-1.66 (m, 2H), 1.68-1.76
(M, 2 H), 1.82 (broad quinte
t, J = 6.6 Hz, 4 H), 4.02 (t, J =
6.6 Hz, 4 H), 5.16 (broad sex
tet, J = 6.2 Hz, 2 H), 7.01 (d, J
= 8.8 Hz, 4 H), 7.31 (d, J = 8.7)
Hz, 4 H), 7.59 (d, J = 8.8 Hz, 4
H), 7.70 (d, J = 8.5 Hz, 4 H), 8.
13 (d, J = 8.7 Hz, 4 H), 8.23 (d,
J = 8.5 Hz, 4 H), IR (KBr) 2900,
2850, 1730, 1715, 1600, 1500,
1465, 1265, 1200, 1160, 1110,
1070, 1010, 830, 760, 690 cm -1 (5) (S, S) -2,15-bis {4- [4- (4-
Electro-Optical Properties of Octyloxyphenyl) phenylcarboxy] phenylcarboxy} hexadecane A (S, S) -2,15-bis {4- [4 [4 [4 A liquid crystal thin film cell was prepared by filling-(4-octyloxyphenyl) phenylcarboxy] phenylcarboxy} hexadecane in the isotropic phase. The transmitted light intensity-applied voltage curve when a triangular wave of 40 Vpp and 1 Hz is applied to the liquid crystal cell is as shown in FIG.
(A) and (b) are measured at 140 ° C. and 130 ° C., respectively.
【０１７４】[0174]
【発明の効果】前述のとおり二量体液晶はかなり安定な
反強誘電的な分子配列構造をとるものと考えられる。従
って、反強誘電性が弱くヒステリシスの形状が悪い液晶
あるいは強誘電性液晶に添加することにより、反強誘電
性を強くしてヒステリシスの形状をより望ましい方向に
改善することが期待される。As described above, the dimeric liquid crystal is considered to have a fairly stable antiferroelectric molecular alignment structure. Therefore, it is expected that the antiferroelectricity will be strengthened and the hysteresis shape will be improved in a more desirable direction by adding it to the liquid crystal or the ferroelectric liquid crystal having weak antiferroelectricity and poor hysteresis shape.
【図１】Ａが印加される三角波を、Ｂが市販ネマチツク
液晶の、Ｃは理想的な強誘電性液晶の、Ｄは反強誘電性
液晶の、それぞれの光学応答特性を示す。FIG. 1 shows optical response characteristics of a triangular wave to which A is applied, B is a commercially available nematic liquid crystal, C is an ideal ferroelectric liquid crystal, and D is an antiferroelectric liquid crystal.
【図２】電界印加時、無電界時の液晶分子の三つの安定
した配列状態を（ａ）、（ｂ）、（ｃ）に示す。FIG. 2 shows (a), (b) and (c) three stable alignment states of liquid crystal molecules when an electric field is applied and when no electric field is applied.
【図３】三状態液晶のヒステリシスを示すものであり、
横軸は印加電圧を、縦軸は透過率（％）を示す。FIG. 3 shows hysteresis of a three-state liquid crystal,
The horizontal axis represents the applied voltage and the vertical axis represents the transmittance (%).
【図４】（ａ）は化合物Ａに、８０Ｖｐｐ、１Ｈｚの三
角波を印加したときの透過光強度と印加電圧曲線を上段
に示し、（ｂ）は５０℃における化合物Ａのヒステリシ
スをに示す。FIG. 4 (a) shows the transmitted light intensity and applied voltage curve when a triangular wave of 80 Vpp, 1 Hz was applied to Compound A, and FIG. 4 (b) shows the hysteresis of Compound A at 50 ° C.
【図５】（ａ）は化合物Ａと本発明の式〔II〕の化合物
との９５：５の混合物よりなる液晶組成物に、８０Ｖｐ
ｐ、１Ｈｚの三角波を印加したときの透過光強度と印加
電圧曲線を示し、（ｂ）は５０℃における前記混合物の
ヒステリシスを示す。FIG. 5 (a) shows a liquid crystal composition comprising a mixture of compound A and a compound of the formula [II] of the present invention in a ratio of 95: 5 and 80 Vp.
p shows a transmitted light intensity and an applied voltage curve when a triangular wave of 1 Hz is applied, and (b) shows a hysteresis of the mixture at 50 ° C.
【図６】（ａ）は本発明の式〔Ｘ〕の化合物と式〔XI〕
の化合物との４５：５５の混合物よりなる液晶組成物
（実施例２）に、２５０Ｖｐｐ、０．１Ｈｚの三角波を
印加したときの透過光強度と印加電圧曲線を示し、
（ｂ）は本発明の式〔XIV〕の化合物単独（実施例５）
の１４０℃において４０Ｖｐｐ、０．１Ｈｚの三角波を
印加したときのヒステリシスを示す。FIG. 6 (a) is a compound of formula [X] of the present invention and a compound of formula [XI]
Shows a transmitted light intensity and an applied voltage curve when a triangular wave of 250 Vpp and 0.1 Hz is applied to a liquid crystal composition (Example 2) consisting of a 45:55 mixture with the compound of
(B) is the compound of formula [XIV] of the present invention alone (Example 5)
3 shows hysteresis when a triangular wave of 40 Vpp and 0.1 Hz is applied at 140 ° C.
【図７】（ａ）、（ｂ）、（ｃ）は本発明の式［XV］
に、４０Ｖｐｐ、１Ｈｚの三角波を印加したときの透過
光強度と印加電圧曲線を示し、各々１５０℃、１４０
℃、１３０℃において測定したものである。7 (a), (b) and (c) are the formulas [XV] of the present invention.
Shows the transmitted light intensity and the applied voltage curve when a triangular wave of 40 Vpp and 1 Hz is applied.
Measured at ℃ and 130 ℃.
【図８】（ａ）、（ｂ）は本発明の［XVII］に、４０Ｖ
ｐｐ、１Ｈｚの三角波を印加したときの透過光強度と印
加電圧曲線を示し、各々１４０℃、１３０℃において測
定したものである。8 (a) and (b) are the same as [XVII] of the present invention, 40V
The transmitted light intensity and the applied voltage curve when a triangular wave of 1 pp and 1 Hz is applied are shown at 140 ° C. and 130 ° C., respectively.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 69/76 9546−4Ｈ Ｃ０７Ｃ 69/76 Ａ 69/773 69/773 69/86 69/86 69/92 69/92 69/94 69/94 69/96 9546−4Ｈ 69/96 Ｚ Ｃ０７Ｄ 239/26 Ｃ０７Ｄ 239/26 239/28 239/28 Ｃ０９Ｋ 19/20 9279−4Ｈ Ｃ０９Ｋ 19/20 19/30 19/30 19/32 19/32 19/34 19/34 Ｇ０２Ｆ 1/13 ５００ Ｇ０２Ｆ 1/13 ５００ (72)発明者 楠本 哲生 神奈川県相模原市西大沼４−４−１ 財団 法人 相模中央化学研究所内 (72)発明者 檜山 爲次郎 神奈川県相模原市西大沼４−４−１ 財団 法人 相模中央化学研究所内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical indication location C07C 69/76 9546-4H C07C 69/76 A 69/773 69/773 69/86 69/86 69 / 92 69/92 69/94 69/94 69/96 9546-4H 69/96 Z C07D 239/26 C07D 239/26 239/28 239/28 C09K 19/20 9279-4H C09K 19/20 19/30 19 / 30 19/32 19/32 19/34 19/34 G02F 1/13 500 G02F 1/13 500 (72) Inventor Tetsuo Kusumoto 4-4-1 Nishionuma, Sagamihara-shi, Kanagawa Sagami Central Chemical Research Institute ( 72) Inventor Hiyama Hiujiro 4-4-1 Nishionuma, Sagamihara City, Kanagawa Prefecture Sagami Central Chemical Research Institute
Claims (8)
炭素数１〜１８のアルキル基よりなる群からそれぞれ独
立して選ばれた基であり、Ｒ2、Ｒ4はＣＦ3およびＣＨ3
よりなる群からそれぞれ独立して選ばれた基であり、Ｘ
1、Ｘ2は単結合、−Ｏ−、−ＣＯＯ−、−ＯＣＯ−およ
び−ＯＣＯＯ−よりなる群からそれぞれ独立して選ばれ
た基であり、Ｙ1、Ｙ2およびＺ1、Ｚ2は単結合、−ＣＯ
Ｏ−、−ＯＣＯ−、−ＣＨ2Ｏ−、−ＯＣＨ2−、−Ｃ≡
Ｃ−よりなる群からそれぞれ独立して選ばれた基であ
り、環Ａ1、環Ａ2、環Ｂ1、環Ｂ2、環Ｃ1および環Ｃ2は
１個または２個のフッ素原子で置換されていてもよい
１，４−フェニレン基、トランス−１，４−シクロヘキ
シレン基、ピリミジン−２，５−ジイル基、ピリジン−
２，５−ジイル基および２，６−ナフチレン基よりなる
群からそれぞれ独立して選ばれた基であり、ｍは７〜２
０の整数、ｎ1、ｎ2は１および０よりなる群からそれぞ
れ独立して選ばれた整数であり、＊は不斉炭素を示
す。）で示される化合物であることを特徴とする二量体
型光学活性化合物。1. The following general formula [I]: (In the formula, R 1 and R 3 are groups independently selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, which may each have a substituent, and R 2 and R 4 are CF 3 and CH 3
X is a group independently selected from the group consisting of
1 , X 2 is a group independently selected from the group consisting of a single bond, —O—, —COO—, —OCO— and —OCOO—, and Y 1 , Y 2 and Z 1 , Z 2 are Single bond, -CO
O -, - OCO -, - CH 2 O -, - OCH 2 -, - C≡
C-is a group independently selected from the group consisting of C-, wherein ring A 1 , ring A 2 , ring B 1 , ring B 2 , ring C 1 and ring C 2 are 1 or 2 fluorine atoms. Optionally substituted 1,4-phenylene group, trans-1,4-cyclohexylene group, pyrimidine-2,5-diyl group, pyridine-
It is a group independently selected from the group consisting of a 2,5-diyl group and a 2,6-naphthylene group, and m is 7 to 2
An integer of 0, n 1 and n 2 are integers independently selected from the group consisting of 1 and 0, and * represents an asymmetric carbon. ) A dimer type optically active compound, which is a compound represented by
Ｙ2が単結合である請求項１記載の二量体型光学活性化
合物。2. The dimeric optically active compound according to claim 1 , wherein Y 1 and Y 2 in the general formula [I] are single bonds.
Ｚ2が−ＣＯＯ−である請求項２記載の二量体型光学活
性化合物。3. The dimer type optically active compound according to claim 2 , wherein Z 1 and Z 2 in the general formula [I] are —COO—.
び環Ｃ2が１個または２個のフッ素原子により置換され
てもよい、１，４−フェニレン基または２，６−ナフチ
レン基である請求項３記載の二量体型光学活性化合物。4. In the general formula [I], ring C 1 and ring C 2 are each a 1,4-phenylene group or a 2,6-naphthylene group which may be substituted by one or two fluorine atoms. The dimeric optically active compound according to claim 3.
請求項１記載の二量体型光学活性化合物。5. The dimer type optically active compound according to claim 1, which exhibits an antiferroelectric chiral smectic phase.
を含有することを特徴とする液晶組成物。6. A liquid crystal composition comprising the dimer type optically active compound according to claim 1. Description:
請求項６記載の液晶組成物。7. The liquid crystal composition according to claim 6, which exhibits an antiferroelectric chiral smectic phase.
いたことを特徴とする液晶表示素子。8. A liquid crystal display device using the liquid crystal composition according to claim 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20788395A JPH08217728A (en) | 1994-12-16 | 1995-07-21 | Dimer-type optically active compound |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33393394 | 1994-12-16 | ||
| JP6-333933 | 1994-12-16 | ||
| JP20788395A JPH08217728A (en) | 1994-12-16 | 1995-07-21 | Dimer-type optically active compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08217728A true JPH08217728A (en) | 1996-08-27 |
Family
ID=26516528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20788395A Pending JPH08217728A (en) | 1994-12-16 | 1995-07-21 | Dimer-type optically active compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08217728A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000050535A1 (en) * | 1999-02-24 | 2000-08-31 | Deutsche Telekom Ag | Liquid crystalline materials for optic phase modulation |
| WO2003099960A1 (en) * | 2002-05-29 | 2003-12-04 | Japan Science And Technology Agency | Antiferroelectric liquid crystal and its manufacturing method |
| JP2004133464A (en) * | 2002-10-08 | 2004-04-30 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| JP2015532649A (en) * | 2012-08-29 | 2015-11-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Bimesogenic compounds and mesogenic media |
| JP2017528429A (en) * | 2014-07-17 | 2017-09-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Bimesogenic compounds and mesogenic media |
-
1995
- 1995-07-21 JP JP20788395A patent/JPH08217728A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000050535A1 (en) * | 1999-02-24 | 2000-08-31 | Deutsche Telekom Ag | Liquid crystalline materials for optic phase modulation |
| JP2002537474A (en) * | 1999-02-24 | 2002-11-05 | ドイッチェ テレコム アーゲー | Liquid crystal material for optical phase modulation |
| US6649087B1 (en) | 1999-02-24 | 2003-11-18 | Deutsche Telekom Ag | Liquid crystalline materials for optical phase modulation |
| WO2003099960A1 (en) * | 2002-05-29 | 2003-12-04 | Japan Science And Technology Agency | Antiferroelectric liquid crystal and its manufacturing method |
| US7211201B2 (en) | 2002-05-29 | 2007-05-01 | Japan Science And Technology Agency | Antiferroelectric liquid crystal and its manufacturing method |
| JP2004133464A (en) * | 2002-10-08 | 2004-04-30 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| JP4642334B2 (en) * | 2002-10-08 | 2011-03-02 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Liquid crystal medium and liquid crystal display |
| JP2015532649A (en) * | 2012-08-29 | 2015-11-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Bimesogenic compounds and mesogenic media |
| JP2017528429A (en) * | 2014-07-17 | 2017-09-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Bimesogenic compounds and mesogenic media |
| US10450508B2 (en) | 2014-07-17 | 2019-10-22 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
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