JPH05170679A - Monofluoroalkane derivative and liquid crystal composition - Google Patents
Monofluoroalkane derivative and liquid crystal compositionInfo
- Publication number
- JPH05170679A JPH05170679A JP3357302A JP35730291A JPH05170679A JP H05170679 A JPH05170679 A JP H05170679A JP 3357302 A JP3357302 A JP 3357302A JP 35730291 A JP35730291 A JP 35730291A JP H05170679 A JPH05170679 A JP H05170679A
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- JP
- Japan
- Prior art keywords
- chf
- liquid crystal
- compound
- group
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 41
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- -1 1- fluoro-1,2-bis(4-n-propylphenyl)ethane Chemical compound 0.000 claims abstract description 29
- 125000004956 cyclohexylene group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 abstract description 9
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 abstract description 7
- 150000002440 hydroxy compounds Chemical class 0.000 abstract description 3
- 150000002576 ketones Chemical class 0.000 abstract description 3
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- QQLFXUGZJVFNEE-UHFFFAOYSA-N 1-(2-benzylphenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=CC=C1CC1=CC=CC=C1 QQLFXUGZJVFNEE-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VIWUJKBBJRFTMC-UHFFFAOYSA-N (1,2-difluoro-2-phenylethenyl)benzene Chemical compound C=1C=CC=CC=1C(F)=C(F)C1=CC=CC=C1 VIWUJKBBJRFTMC-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- XNKCGQLMBAAZNI-UHFFFAOYSA-N 1,2-diphenylpentan-1-one Chemical compound C=1C=CC=CC=1C(CCC)C(=O)C1=CC=CC=C1 XNKCGQLMBAAZNI-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DMUVQFCRCMDZPW-UHFFFAOYSA-N 1-ethyl-2-propylbenzene Chemical compound CCCC1=CC=CC=C1CC DMUVQFCRCMDZPW-UHFFFAOYSA-N 0.000 description 1
- LGSVIPDJPGLDNM-UHFFFAOYSA-N 3,3,3-trifluoro-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(C(F)(F)F)C(=O)C1=CC=CC=C1 LGSVIPDJPGLDNM-UHFFFAOYSA-N 0.000 description 1
- DYKMICWOBLSRIW-UHFFFAOYSA-N 4-ethyl-2-fluoro-1-methylbenzene Chemical compound CCC1=CC=C(C)C(F)=C1 DYKMICWOBLSRIW-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、モノフルオロアルカン
誘導体化合物及びそれを含有する液晶組成物に関するも
のである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a monofluoroalkane derivative compound and a liquid crystal composition containing it.
【０００２】[0002]
【従来の技術】液晶表示素子は、時計，電卓をはじめ、
近年では測定器、自動車用計器、複写器、カメラ、ＯＡ
機器用表示装置、家電製品用表示装置等種々の用途に使
用され始めており、広い動作温度範囲、低動作電圧、高
速応答性、高コントラスト比、広視角、化学的安定性等
の種々の性能要求がなされている。2. Description of the Related Art Liquid crystal display devices include clocks, calculators,
In recent years, measuring instruments, automobile instruments, copying machines, cameras, OA
It has begun to be used in various applications such as device display devices and home appliance display devices, and various performance requirements such as wide operating temperature range, low operating voltage, high-speed response, high contrast ratio, wide viewing angle, chemical stability, etc. Has been done.
【０００３】しかし、現在のところ、これらの特性を単
独の材料で全て満たす材料はなく、複数の液晶、及び非
液晶の材料を混合して液晶組成物として要求性能を満た
している状態である。このため、各種特性のすべてでは
なく、一又は二以上の特性に優れた液晶又は非液晶の材
料開発が望まれている。However, at present, there is no material satisfying all of these characteristics with a single material, and a plurality of liquid crystal and non-liquid crystal materials are mixed to satisfy the required performance as a liquid crystal composition. Therefore, it is desired to develop a liquid crystal or non-liquid crystal material excellent in one or two or more of all characteristics.
【０００４】[0004]
【発明が解決しようとする課題】液晶を用いた表示素子
分野においては、その性能向上が望まれており、低電圧
駆動、高精細表示、高コントラスト比、広視角特性、低
温応答特性、広動作温度範囲等が望まれおり、これらは
いずれかを向上させると他のいずれかが犠牲になるとい
う傾向がある。In the field of display devices using liquid crystals, it is desired to improve their performance, and low voltage driving, high definition display, high contrast ratio, wide viewing angle characteristics, low temperature response characteristics, wide operation are required. A temperature range or the like is desired, and any one of these tends to be sacrificed when the other is improved.
【０００５】特に、最近、電池駆動においては低電圧駆
動と高速応答、ＯＡ機器等においては高精細表示と高速
応答、自動車用表示等においては低温応答もしくは広動
作温度範囲で高速応答というように、その応答速度を向
上させることが望まれている。In particular, recently, low voltage driving and high speed response in battery drive, high definition display and high speed response in OA equipment, low temperature response in automobile display etc. or high speed response in wide operating temperature range have been made. It is desired to improve the response speed.
【０００６】このためには、いくつかの改善方法が考え
られるが、その一つとして低粘性の液晶組成物の採用が
ある。即ち、液晶組成物の粘性が低下すれば、応答速度
は向上し、低温でも実用的な速度での表示が可能にな
る。また、従来と同じ応答速度でよければ、より低電圧
で駆動できたり、より高いデューティ駆動が可能、即
ち、高精細駆動が可能になる。To solve this problem, some improvement methods can be considered. One of them is to adopt a low viscosity liquid crystal composition. That is, when the viscosity of the liquid crystal composition is reduced, the response speed is improved, and it is possible to display at a practical speed even at a low temperature. Further, if the response speed is the same as that of the conventional one, it is possible to drive with a lower voltage or drive with a higher duty, that is, high-definition drive becomes possible.
【０００７】このような目的のため、第16回液晶討論会
で講演されたようなp,p'- 二置換ジフルオロスチルベン
化合物が提案されている。この化合物は以下の一般式
(3) で示されるような化学構造を有している。For this purpose, a p, p'-disubstituted difluorostilbene compound as proposed at the 16th liquid crystal debate has been proposed. This compound has the general formula
It has a chemical structure as shown in (3).
【０００８】[0008]
【化１】 [Chemical 1]
【０００９】ただし、一般式(3) のRA、RBはn-アルキル
基、n-アルコキシ基、n-アルコキシカルボニル基を意味
する。However, R A and R B in the general formula (3) mean an n-alkyl group, an n-alkoxy group and an n-alkoxycarbonyl group.
【００１０】この一般式(3) の化合物は、低粘性でフッ
素置換されていないスチルベン化合物よりも光に対する
安定性が向上しているものであった。しかし、通常使用
されている一般の液晶化合物に比しては、光に対する安
定性がまだ劣っており、使用環境が限定されたり、紫外
線カットフィルターを併用せざるを得ないことが多かっ
た。The compound of the general formula (3) had low viscosity and improved stability to light as compared with a stilbene compound which was not substituted with fluorine. However, the stability against light is still inferior to the commonly used general liquid crystal compounds, and the use environment is limited, and it is often necessary to use an ultraviolet cut filter together.
【００１１】従って、低粘性で光に対する安定性が高い
液晶材料が望まれていた。Therefore, a liquid crystal material having low viscosity and high stability to light has been desired.
【００１２】[0012]
【課題を解決するための手段】本発明は、前述の課題を
解決すべく、新規な材料を提供するものであり、一般 式(1) R1-(A1)m-Y1-A2-CH2CHF-A3-Y2-(A4)n-R2 （式中、A1〜A4は相互に独立してトランス-1,4- ジ置換
シクロヘキシレン基または1,4-ジ置換フェニレン基であ
り、これらの基は夫々非置換であるかあるいは置換基と
して１個もしくは２個以上のハロゲン、シアノ基を有し
ていてもよく、これらの基中に存在する１個もしくは２
個以上のCH基は窒素原子に置換されていてもよく、Y1、
Y2は相互に独立して-COO-,-OCO-,-C≡C-,-CH2CH2-,-OCH
2-,-CH2O-または単結合を示し、m,n は 0または 1を示
し、R1及びR2は相互に独立して炭素数 1〜10のアルキル
基、ハロゲン、シアノ基を示し、アルキル基の場合に
は、炭素−炭素結合間あるいはこの基と環との間の炭素
−炭素結合間に酸素原子が挿入されてもよく、また、そ
の炭素−炭素結合の一部が二重結合にされていてもよ
く、また、その１個の-CH2- 基がカルボニル基に置換さ
れていてもよく、また、その基中の水素原子の一部もし
くは全てがフッ素原子で置換されていてもよい）で表さ
れることを特徴とするモノフルオロアルカン誘導体化合
物を提供するものである。SUMMARY OF THE INVENTION The present invention provides a novel material to solve the above-mentioned problems, and has a general formula (1) R 1- (A 1 ) m -Y 1 -A 2 -CH 2 CHF-A 3 -Y 2- (A 4 ) n -R 2 (In the formula, A 1 to A 4 are independently of each other a trans-1,4-di-substituted cyclohexylene group or 1,4- A di-substituted phenylene group, each of which is unsubstituted or may have one or more halogen or cyano group as a substituent, and one or more of these groups may be present. Two
One or more CH groups may be substituted with a nitrogen atom, Y 1 ,
Y 2 is independently of each other -COO-,-OCO-,-C≡C-,-CH 2 CH 2 -,-OCH
2- , -CH 2 O- or a single bond, m, n are 0 or 1, R 1 and R 2 are each independently a C 1-10 alkyl group, a halogen, a cyano group. In the case of an alkyl group, an oxygen atom may be inserted between the carbon-carbon bond or between the carbon-carbon bond between this group and the ring, and a part of the carbon-carbon bond has a double bond. It may be a bond, or one of the —CH 2 — groups may be substituted with a carbonyl group, and some or all of the hydrogen atoms in the group may be substituted with a fluorine atom. It may also be represented by the formula (1).
【００１３】また、一般式(2) R1-A2-CH2CHF-A3-R2 （式中、A2、A3、R1及びR2については、前記と同じもの
を示す）で表されることを特徴とするモノフルオロアル
カン誘導体化合物、及び、一般式(1) または一般式(2)
で示される化合物を含有することを特徴とする液晶組成
物を提供するものである。The general formula (2) R 1 -A 2 -CH 2 CHF-A 3 -R 2 (in the formula, A 2 , A 3 , R 1 and R 2 are the same as above) And a monofluoroalkane derivative compound represented by the general formula (1) or general formula (2)
The present invention provides a liquid crystal composition containing a compound represented by:
【００１４】本発明の一般式(1) の化合物は、比較的小
さい屈折率異方性（△n)を有しており、低粘性であり、
かつ、他の液晶又は非液晶との相溶性に優れ、化学的に
も安定な、特に光に対して安定な材料である。The compound of the general formula (1) of the present invention has a relatively small refractive index anisotropy (Δn), low viscosity,
In addition, it is a material that has excellent compatibility with other liquid crystals or non-liquid crystals and is chemically stable, particularly, stable to light.
【００１５】本発明の化合物の具体的構造としては、以
下のような化合物がある。その代表的化合物として、環
の数が２個の化合物として以下のような化合物がある。 R1-A2-CH2CHF-A3-R2 (2)Specific structures of the compound of the present invention include the following compounds. As typical compounds thereof, there are the following compounds as compounds having two rings. R 1 -A 2 -CH 2 CHF-A 3 -R 2 (2)
【００１６】一般式(2) の化合物としては、より具体的
には、以下のような化合物がある。なお、以下の説明に
おいては、一般式(2) の化合物に限らず、「-Ph-」は1,
4-ジ置換フェニレン基を表し、「-Cy-」はトランス-1,4
- ジ置換シクロヘキシレン基を表す。 R1-Ph-CH2CHF-Ph-R2 (2A)More specifically, the compound of the general formula (2) includes the following compounds. In the following description, not only the compound of the general formula (2), but "-Ph-" is 1,
Represents a 4-disubstituted phenylene group, "-Cy-" is trans-1,4
Represents a di-substituted cyclohexylene group. R 1 -Ph-CH 2 CHF-Ph-R 2 (2A)
【００１７】[0017]
【化２】 [Chemical 2]
【００１８】その1,4-ジ置換フェニレン基の１つまたは
２つをトランス-1,4- ジ置換シクロヘキシレン基に置換
した化合物として以下のような化合物がある。 R1-Cy-CH2CHF-Ph-R2 (2B) R1-Ph-CH2CHF-Cy-R2 (2C) R1-Cy-CH2CHF-Cy-R2 (2D)The following compounds are examples of compounds in which one or two of the 1,4-di-substituted phenylene groups are replaced with trans-1,4-di-substituted cyclohexylene groups. R 1 -Cy-CH 2 CHF-Ph-R 2 (2B) R 1 -Ph-CH 2 CHF-Cy-R 2 (2C) R 1 -Cy-CH 2 CHF-Cy-R 2 (2D)
【００１９】また、その1,4-ジ置換フェニレン基を一部
の水素原子がフッ素原子に置換されたフェニレン基とし
た化合物として以下のような化合物がある。 R1-Ph-CH2CHF-PhF-R2 (2E)Further, there are the following compounds as a compound in which the 1,4-disubstituted phenylene group is a phenylene group in which some hydrogen atoms are replaced by fluorine atoms. R 1 -Ph-CH 2 CHF-PhF-R 2 (2E)
【００２０】[0020]
【化３】 [Chemical 3]
【００２１】また、環の数が３個の化合物として、以下
のような化合物がある。 R1-A1-A2-CH2CHF-A3-R2 (4) R1-A2-CH2CHF-A3-A4-R2 (5)Further, as a compound having three rings, there are the following compounds. R 1 -A 1 -A 2 -CH 2 CHF-A 3 -R 2 (4) R 1 -A 2 -CH 2 CHF-A 3 -A 4 -R 2 (5)
【００２２】一般式(5) の化合物としては、より具体的
には以下のような化合物がある。 R1-Ph-Ph-CH2CHF-Ph-R2 (4A) R1-Ph-CH2CHF-Ph-Ph-R2 (5A)More specifically, the compound of the general formula (5) includes the following compounds. R 1 -Ph-Ph-CH 2 CHF-Ph-R 2 (4A) R 1 -Ph-CH 2 CHF-Ph-Ph-R 2 (5A)
【００２３】[0023]
【化４】 [Chemical 4]
【００２４】その1,4-ジ置換フェニレン基の１つ乃至３
つをトランス-1,4- ジ置換シクロヘキシレン基に置換し
た化合物として以下のような化合物がある。 R1-Cy-Ph-CH2CHF-Ph-R2 (4B) R1-Ph-Cy-CH2CHF-Ph-R2 (4C) R1-Ph-Ph-CH2CHF-Cy-R2 (4D) R1-Cy-Cy-CH2CHF-Ph-R2 (4E) R1-Cy-Ph-CH2CHF-Cy-R2 (4F) R1-Ph-Cy-CH2CHF-Cy-R2 (4G) R1-Cy-Cy-CH2CHF-Cy-R2 (4H)One to three of the 1,4-disubstituted phenylene groups
Examples of compounds in which one is substituted with a trans-1,4-di-substituted cyclohexylene group include the following compounds. R 1 -Cy-Ph-CH 2 CHF-Ph-R 2 (4B) R 1 -Ph-Cy-CH 2 CHF-Ph-R 2 (4C) R 1 -Ph-Ph-CH 2 CHF-Cy-R 2 (4D) R 1 -Cy-Cy-CH 2 CHF-Ph-R 2 (4E) R 1 -Cy-Ph-CH 2 CHF-Cy-R 2 (4F) R 1 -Ph-Cy-CH 2 CHF -Cy-R 2 (4G) R 1 -Cy-Cy-CH 2 CHF-Cy-R 2 (4H)
【００２５】 R1-Cy-CH2CHF-Ph-Ph-R2 (5B) R1-Ph-CH2CHF-Cy-Ph-R2 (5C) R1-Ph-CH2CHF-Ph-Cy-R2 (5D) R1-Cy-CH2CHF-Cy-Ph-R2 (5E) R1-Cy-CH2CHF-Ph-Cy-R2 (5F) R1-Ph-CH2CHF-Cy-Cy-R2 (5G) R1-Cy-CH2CHF-Cy-Cy-R2 (5H)R 1 -Cy-CH 2 CHF-Ph-Ph-R 2 (5B) R 1 -Ph-CH 2 CHF-Cy-Ph-R 2 (5C) R 1 -Ph-CH 2 CHF-Ph- Cy-R 2 (5D) R 1 -Cy-CH 2 CHF-Cy-Ph-R 2 (5E) R 1 -Cy-CH 2 CHF-Ph-Cy-R 2 (5F) R 1 -Ph-CH 2 CHF-Cy-Cy-R 2 (5G) R 1 -Cy-CH 2 CHF-Cy-Cy-R 2 (5H)
【００２６】また、その1,4-ジ置換フェニレン基を一部
の水素原子がフッ素原子に置換されたフェニレン基とし
た化合物として以下のような化合物がある。 R1-Ph-Ph-CH2CHF-PhF-R2 (4I) R1-Ph-CH2CHF-Ph-PhF-R2 (5I)Further, there is the following compound as a compound in which the 1,4-disubstituted phenylene group is a phenylene group in which some hydrogen atoms are replaced by fluorine atoms. R 1 -Ph-Ph-CH 2 CHF-PhF-R 2 (4I) R 1 -Ph-CH 2 CHF-Ph-PhF-R 2 (5I)
【００２７】また、環の数が４個の化合物として、以下
のような化合物がある。 R1-A1-A2-CH2CHF-A3-A4-R2 (6)Further, there are the following compounds as compounds having four rings. R 1 -A 1 -A 2 -CH 2 CHF-A 3 -A 4 -R 2 (6)
【００２８】一般式(5) の化合物としては、より具体的
には以下のような化合物がある。 R1-Ph-Ph-CH2CHF-Ph-Ph-R2 (6A)More specifically, the compound of the general formula (5) includes the following compounds. R 1 -Ph-Ph-CH 2 CHF-Ph-Ph-R 2 (6A)
【００２９】[0029]
【化５】 [Chemical 5]
【００３０】 R1-Cy-Ph-CH2CHF-Ph-Ph-R2 (6B) R1-Cy-Ph-CH2CHF-Ph-Cy-R2 (6C) R1-Ph-Cy-CH2CHF-Ph-Ph-R2 (6D) R1-Ph-Ph-CH2CHF-Cy-Ph-R2 (6E) R1-Ph-Ph-CH2CHF-Ph-PhF-R2 (6F) R1-Ph-Ph-CH2CHF-PhF-Ph-R2 (6G)R 1 -Cy-Ph-CH 2 CHF-Ph-Ph-R 2 (6B) R 1 -Cy-Ph-CH 2 CHF-Ph-Cy-R 2 (6C) R 1 -Ph-Cy- CH 2 CHF-Ph-Ph-R 2 (6D) R 1 -Ph-Ph-CH 2 CHF-Cy-Ph-R 2 (6E) R 1 -Ph-Ph-CH 2 CHF-Ph-PhF-R 2 (6F) R 1 -Ph-Ph-CH 2 CHF-PhF-Ph-R 2 (6G)
【００３１】このほか、３環以上の化合物の場合、環と
環との間のY1、Y2を単結合以外に変更した以下のような
化合物もある。In addition, in the case of a compound having three or more rings, there are the following compounds in which Y 1 and Y 2 between the rings are changed to other than a single bond.
【００３２】 R1-Ph-COO-Ph-CH2CHF-Ph-R2 (4J) R1-Ph-OCO-Ph-CH2CHF-Ph-R2 (4K) R1-Ph-C ≡C-Ph-CH2CHF-Ph-R2 (4L) R1-Ph-CH2CH2-Ph-CH2CHF-Ph-R2 (4M) R1-Ph-OCH2-Ph-CH2CHF-Ph-R2 (4N) R1-Ph-CH2O-Ph-CH2CHF-Ph-R2 (4O)R 1 -Ph-COO-Ph-CH 2 CHF-Ph-R 2 (4J) R 1 -Ph-OCO-Ph-CH 2 CHF-Ph-R 2 (4K) R 1 -Ph-C ≡ C-Ph-CH 2 CHF-Ph-R 2 (4L) R 1 -Ph-CH 2 CH 2 -Ph-CH 2 CHF-Ph-R 2 (4M) R 1 -Ph-OCH 2 -Ph-CH 2 CHF-Ph-R 2 (4N) R 1 -Ph-CH 2 O-Ph-CH 2 CHF-Ph-R 2 (4O)
【００３３】 R1-Ph-CH2CHF-Ph-COO-Ph-R2 (5J) R1-Ph-CH2CHF-Ph-OCO-Ph-R2 (5K) R1-Ph-CH2CHF-Ph-C ≡C-Ph-R2 (5L) R1-Ph-CH2CHF-Ph-CH2CH2-Ph-R2 (5M) R1-Ph-CH2CHF-Ph-OCH2-Ph-R2 (5N) R1-Ph-CH2CHF-Ph-CH2O-Ph-R2 (5O)R 1 -Ph-CH 2 CHF-Ph-COO-Ph-R 2 (5J) R 1 -Ph-CH 2 CHF-Ph-OCO-Ph-R 2 (5K) R 1 -Ph-CH 2 CHF-Ph-C ≡ C-Ph-R 2 (5L) R 1 -Ph-CH 2 CHF-Ph-CH 2 CH 2 -Ph-R 2 (5M) R 1 -Ph-CH 2 CHF-Ph-OCH 2 -Ph-R 2 (5N) R 1 -Ph-CH 2 CHF-Ph-CH 2 O-Ph-R 2 (5O)
【００３４】 R1-Ph-COO-Ph-CH2CHF-Ph-Ph-R2 (6H) R1-Ph-OCO-Ph-CH2CHF-Ph-Ph-R2 (6I) R1-Ph-C ≡C-Ph-CH2CHF-Ph-Ph-R2 (6J) R1-Ph-CH2CH2-Ph-CH2CHF-Ph-Ph-R2 (6K) R1-Ph-OCH2-Ph-CH2CHF-Ph-Ph-R2 (6L) R1-Ph-CH2O-Ph-CH2CHF-Ph-Ph-R2 (6M) R1-Ph-COO-Ph-CH2CHF-Ph-OCO-Ph-R2 (6N)R 1 -Ph-COO-Ph-CH 2 CHF-Ph-Ph-R 2 (6H) R 1 -Ph-OCO-Ph-CH 2 CHF-Ph-Ph-R 2 (6I) R 1- Ph-C ≡ C-Ph-CH 2 CHF-Ph-Ph-R 2 (6J) R 1 -Ph-CH 2 CH 2 -Ph-CH 2 CHF-Ph-Ph-R 2 (6K) R 1 -Ph -OCH 2 -Ph-CH 2 CHF-Ph-Ph-R 2 (6L) R 1 -Ph-CH 2 O-Ph-CH 2 CHF-Ph-Ph-R 2 (6M) R 1 -Ph-COO- Ph-CH 2 CHF-Ph-OCO-Ph-R 2 (6N)
【００３５】また、A1〜A4の基を、1,4-ジ置換フェニレ
ン基、トランス-1,4- ジ置換シクロヘキシレン基以外の
環構造を有する基とした以下のような化合物もある。There are also the following compounds in which the groups A 1 to A 4 are groups having a ring structure other than the 1,4-di-substituted phenylene group and the trans-1,4-di-substituted cyclohexylene group. ..
【００３６】[0036]
【化６】 [Chemical 6]
【００３７】本発明の上記のような化合物は、他の液晶
材料または非液晶材料と混合して液晶組成物にすること
により、その液晶組成物を低粘性とすることができ、液
晶表示素子とした場合に高速応答が可能になる。By mixing the above-mentioned compound of the present invention with another liquid crystal material or a non-liquid crystal material to form a liquid crystal composition, the liquid crystal composition can have a low viscosity and can be used as a liquid crystal display device. In that case, high-speed response becomes possible.
【００３８】本発明の一般式(1) の化合物は、他の液
晶、非液晶に、少なくとも１種を混合することにより液
晶組成物として使用される。The compound of the general formula (1) of the present invention is used as a liquid crystal composition by mixing at least one kind with other liquid crystal and non-liquid crystal.
【００３９】本発明の化合物と混合させる物質として
は、例えば以下のようなものがある。なお、以下の式で
のRC、RDはアルキル基、アルコキシ基、ハロゲン原子、
シアノ基等の基を表わす。Examples of substances to be mixed with the compound of the present invention are as follows. In the formula below, R C and R D are an alkyl group, an alkoxy group, a halogen atom,
Represents a group such as a cyano group.
【００４０】RC-Cy-Cy-RD RC-Cy-Ph-RD RC-Ph-Ph-RD R C -Cy-Cy-R D R C -Cy-Ph-R D R C -Ph-Ph-R D
【００４１】RC-Cy-COO-Ph-RD RC-Ph-COO-Ph-RD RC-Cy-CH=CH-Ph-RD RC-Ph-CH=CH-Ph-RD RC-Cy-CH2CH2-Ph-RD RC-Ph-CH2CH2-Ph-RD RC-Ph-N=N-Ph-RD RC-Ph-NON-Ph-RD RC-Cy-COS-Ph-RD R C -Cy-COO-Ph-R D R C -Ph-COO-Ph-R D R C -Cy-CH = CH-Ph-R D R C -Ph-CH = CH-Ph-R D R C -Cy-CH 2 CH 2 -Ph-R D R C -Ph-CH 2 CH 2 -Ph-R D R C -Ph-N = N-Ph-R D R C -Ph-NON-Ph -R D R C -Cy-COS-Ph-R D
【００４２】RC-Cy-Ph-Ph-RD RC-Cy-Ph-Ph-Cy-RD RC-Ph-Ph-Ph-RD RC-Cy-COO-Ph-Ph-RD RC-Cy-Ph-COO-Ph-RD RC-Cy-COO-Ph-COO-Ph-RD RC-Ph-COO-Ph-COO-Ph-RD RC-Ph-COO-Ph-OCO-Ph-RD R C -Cy-Ph-Ph-R D R C -Cy-Ph-Ph-Cy-R D R C -Ph-Ph-Ph-R D R C -Cy-COO-Ph-Ph-R D R C -Cy-Ph-COO-Ph-R D R C -Cy-COO-Ph-COO-Ph-R D R C -Ph-COO-Ph-COO-Ph-R D R C -Ph-COO -Ph-OCO-Ph-R D
【００４３】[0043]
【化７】 [Chemical 7]
【００４４】なお、これらの化合物は単なる例示にすぎ
なく、環構造もしくは末端基の水素原子のハロゲン原
子、シアノ基、メチル基等への置換、シクロヘキサン
環、ベンゼン環の他の六員環、五員環等への置換、環の
間の結合基の変更等が可能であり、所望の性能に合わせ
て種々の材料が選択使用されればよい。These compounds are merely examples, and the substitution of a hydrogen atom of a ring structure or a terminal group with a halogen atom, a cyano group, a methyl group, etc., a cyclohexane ring, another six-membered ring of a benzene ring, and a pentagonal ring. Substitution with a member ring or the like, change of a bonding group between the rings, and the like are possible, and various materials may be selected and used according to desired performance.
【００４５】本発明の組成物は、液晶組成物として、電
極付の基板間に配され、ツイストネマチック方式、ゲス
ト・ホスト方式、動的散乱方式、フェーズチェンジ方
式、ＤＡＰ方式、二周波駆動方式、強誘電性液晶表示方
式等種々のモードで使用することができる。The composition of the present invention is disposed as a liquid crystal composition between substrates with electrodes, and is a twisted nematic system, a guest-host system, a dynamic scattering system, a phase change system, a DAP system, a dual frequency drive system, It can be used in various modes such as a ferroelectric liquid crystal display system.
【００４６】具体的には、次のようなものが代表的であ
る。プラスチック、ガラス等の基板上に、必要に応じて
SiO2、Al2O3 等のアンダーコート層やカラーフィルター
層を形成し、In2O3-SnO2（ＩＴＯ）、SnO2等の電極を設
け、パターニングした後、必要に応じてポリイミド、ポ
リアミド、SiO2、Al2O3 等のオーバーコート層を形成
し、配向処理し、これにシール材を印刷し、電極面が相
対向するように配して周辺をシールし、シール材を硬化
して空セルを形成する。Specifically, the followings are typical. If necessary, on a substrate such as plastic or glass
SiO 2 , Al 2 O 3 etc. undercoat layer or color filter layer is formed, In 2 O 3 -SnO 2 (ITO), SnO 2 etc. electrodes are provided, and after patterning, polyimide, polyamide as required , SiO 2 , Al 2 O 3 etc. are formed, orientation treatment is applied, printing sealing material is printed on this, the electrodes are arranged so that they face each other, the periphery is sealed, and the sealing material is cured. To form an empty cell.
【００４７】この空セルに、本発明の化合物を含む組成
物を注入し、注入口を封止剤で封止して液晶セルを構成
する。この液晶セルに必要に応じて偏光板、カラー偏光
板、光源、カラーフィルター、半透過反射板、反射板、
導光板、紫外線カットフィルター等を積層する、文字，
図形等を印刷する、ノングレア加工する等して液晶表示
素子とする。A composition containing the compound of the present invention is injected into this empty cell, and the injection port is sealed with a sealant to form a liquid crystal cell. If necessary, a polarizing plate, a color polarizing plate, a light source, a color filter, a semi-transmissive reflector, a reflector,
Laminated light guide plate, UV cut filter, etc., letters,
A liquid crystal display element is obtained by printing a figure or the like and performing non-glare processing.
【００４８】なお、上述の説明は、液晶表示素子の基本
的な構成及び製法を示したにすぎなく、例えば２層電極
を用いた基板、２層の液晶層を形成した２層液晶セル、
ＴＦＴ、ＭＩＭ等の能動素子を形成したアクティブマト
リクス基板を用いたアクティブマトリクス素子等、種々
の構成のものが使用できる。The above description merely shows the basic structure and manufacturing method of the liquid crystal display element, for example, a substrate using a two-layer electrode, a two-layer liquid crystal cell in which two liquid crystal layers are formed,
Various structures such as an active matrix element using an active matrix substrate on which active elements such as TFT and MIM are formed can be used.
【００４９】本発明の化合物を液晶組成物に用いること
により、高デューティ駆動を行っても、高速応答が期待
できる。このため、近年注目されている高ツイスト角の
スーパーツイスト（ＳＴＮ）型液晶表示素子にも好適で
ある。By using the compound of the present invention in a liquid crystal composition, a high speed response can be expected even when high duty driving is performed. Therefore, it is also suitable for a super twist (STN) type liquid crystal display element having a high twist angle, which has been receiving attention in recent years.
【００５０】本発明の一般式(1) の化合物は、例えば、
次の方法に従って製造される。 The compound of the general formula (1) of the present invention is, for example,
It is manufactured according to the following method.
【００５１】即ち、一般式(7) で表されるケトン誘導体
化合物を水素化ホウ素ナトリウム(8) 等の還元剤と反応
させることによって、ヒドロキシ化合物(9) を得る。次
いで、フッ素化剤であるジエチルアミノサルファートリ
フルオリド(DAST)(10)と反応させることによって、一般
式(1) のモノフルオロアルカン誘導体化合物を得ること
ができる。That is, the hydroxy compound (9) is obtained by reacting the ketone derivative compound represented by the general formula (7) with a reducing agent such as sodium borohydride (8). Then, by reacting with a fluorinating agent, diethylaminosulfur trifluoride (DAST) (10), the monofluoroalkane derivative compound of the general formula (1) can be obtained.
【００５２】これらの製造方法は単なる例示にすぎな
く、種々の製造方法が使用できる。These manufacturing methods are merely examples, and various manufacturing methods can be used.
【００５３】[0053]
実施例１ 100ml の三ツ口フラスコに4,4'- ジ(n- プロピル) ベン
ジルフェニルケトン5.60g(0.02mol)および乾燥エタノー
ル30mlを仕込み、 0℃にて水素化ホウ素ナトリウムを0.
76g(0.02mol)を加え、さらに室温下で 2時間撹拌した。
水を加え、塩化メチレンで抽出し、有機層を水洗後、溶
媒を留去して、1-ヒドロキシ-1,2- ビス(4-n- プロピル
フェニル) エタンを5.36g （収率95％）得た。Example 1 A 100-ml three-necked flask was charged with 5.60 g (0.02 mol) of 4,4'-di (n-propyl) benzylphenyl ketone and 30 ml of dry ethanol, and sodium borohydride was added at 0 ° C to 0.
76 g (0.02 mol) was added, and the mixture was further stirred at room temperature for 2 hours.
After adding water and extracting with methylene chloride, washing the organic layer with water, distilling off the solvent, 5.36 g of 1-hydroxy-1,2-bis (4-n-propylphenyl) ethane (yield 95%) Obtained.
【００５４】次いで、得られた1-ヒドロキシ-1,2- ビス
(2-n- プロピルフェニル) エタン5.36g を乾燥塩化メチ
レン30mlに溶解し、ジエチルアミノサルファートリフル
オリド(DAST)を6.13g(0.038mol) を加えた。室温下で24
時間撹拌後、水を加え、塩化メチレンで抽出した。有機
層を水洗後、溶媒を留去し、得られた粗結晶をシリカゲ
ルカラムクロマトグラフィーにて精製して1-フルオロ-
1,2- ビス(4-n- プロピルフェニル) エタンを4.53g
（収率84％）得た。 n-C3H7-Ph-CH2CHF-Ph-C3H7(n)Then, the obtained 1-hydroxy-1,2-bis
5.36 g of (2-n-propylphenyl) ethane was dissolved in 30 ml of dry methylene chloride, and 6.13 g (0.038 mol) of diethylaminosulfur trifluoride (DAST) was added. 24 at room temperature
After stirring for an hour, water was added and the mixture was extracted with methylene chloride. After washing the organic layer with water, the solvent was distilled off, and the resulting crude crystals were purified by silica gel column chromatography to give 1-fluoro-
4.53 g of 1,2-bis (4-n-propylphenyl) ethane
(Yield 84%) was obtained. nC 3 H 7 -Ph-CH 2 CHF-Ph-C 3 H 7 (n)
【００５５】[0055]
【化８】 [Chemical 8]
【００５６】本化合物の分析結果を以下に示す。19 F NMR(CDCl3) −171.6ppm(m) ＭＳ m/e 284(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. 19 F NMR (CDCl 3 ) -171.6 ppm (m) MS m / e 284 (M + ) IR 1230 cm -1 (CF)
【００５７】実施例２ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4,4'- ジメトキベンジルフェニ
ルケトンを5.12g(0.02mol)用いる以外は実施例１と同様
に反応を行い、1-フルオロ-1,2- ビス(4- メトキシフェ
ニル) エタンを4.21g （収率81％) 得た。 CH3O-Ph-CH2CHF-Ph-OCH3 Example 2 In place of 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 5.12 g (0.02 mol) of 4,4'-dimethoxybenzylphenylketone was used. The reaction was performed in the same manner as in Example 1 to obtain 4.21 g (yield 81%) of 1-fluoro-1,2-bis (4-methoxyphenyl) ethane. CH 3 O-Ph-CH 2 CHF-Ph-OCH 3
【００５８】本化合物の分析結果を以下に示す。 ＭＳ m/e 260(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 260 (M + ) IR 1230cm -1 (CF)
【００５９】実施例３ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4,4'- ジクロロベンジルフェニ
ルケトンを5.30g(0.02mol)用いる以外は実施例１と同様
に反応を行い、1-フルオロ-1,2- ビス(4- クロロフェニ
ル) エタンを4.30g （収率80％) 得た。 Cl-Ph-CH2CHF-Ph-ClExample 3 The procedure of Example 1 was repeated except that 5.40 g (0.02 mol) of 4,4′-dichlorobenzylphenylketone was used instead of 4,4′-di (n-propyl) benzylphenylketone used in Example 1. The reaction was performed in the same manner as in Example 1 to obtain 1-fluoro-1,2-bis (4-chlorophenyl) ethane (4.30 g, yield 80%). Cl-Ph-CH 2 CHF-Ph-Cl
【００６０】本化合物の分析結果を以下に示す。 ＭＳ m/e 269(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 269 (M + ) IR 1230cm -1 (CF)
【００６１】実施例１〜３と同様にして、以下の化合物
を得ることができる。 CH3-Ph-CH2CHF-Ph-CH3 n-C5H11-Ph-CH2CHF-Ph-C5H11(n) n-C7H15-Ph-CH2CHF-Ph-C7H15(n) n-C10H21-Ph-CH2CHF-Ph-C10H21(n)The following compounds can be obtained in the same manner as in Examples 1-3. CH 3 -Ph-CH 2 CHF-Ph-CH 3 nC 5 H 11 -Ph-CH 2 CHF-Ph-C 5 H 11 (n) nC 7 H 15 -Ph-CH 2 CHF-Ph-C 7 H 15 (n) nC 10 H 21 -Ph-CH 2 CHF-Ph-C 10 H 21 (n)
【００６２】CH3O-Ph-CH2CHF-Ph-CH3 CH3-Ph-CH2CHF-Ph-OCH3 n-C3H7O-Ph-CH2CHF-Ph-C3H7(n) n-C3H7O-Ph-CH2CHF-Ph-OC3H7(n) n-C3H7-Ph-CH2CHF-Ph-OC3H7(n) n-C3H7O-Ph-CH2CHF-Ph-C5H11(n)CH 3 O-Ph-CH 2 CHF-Ph-CH 3 CH 3 -Ph-CH 2 CHF-Ph-OCH 3 nC 3 H 7 O-Ph-CH 2 CHF-Ph-C 3 H 7 (n ) nC 3 H 7 O-Ph-CH 2 CHF-Ph-OC 3 H 7 (n) nC 3 H 7 -Ph-CH 2 CHF-Ph-OC 3 H 7 (n) nC 3 H 7 O-Ph- CH 2 CHF-Ph-C 5 H 11 (n)
【００６３】Cl-Ph-CH2CHF-Ph-F CH3-Ph-CH2CHF-Ph-Cl Cl-Ph-CH2CHF-Ph-CH3 CH3O-Ph-CH2CHF-Ph-Cl CH3-Ph-CH2CHF-Ph-F CH3O-Ph-CH2CHF-Ph-FCl-Ph-CH 2 CHF-Ph-F CH 3 -Ph-CH 2 CHF-Ph-Cl Cl-Ph-CH 2 CHF-Ph-CH 3 CH 3 O-Ph-CH 2 CHF-Ph- Cl CH 3 -Ph-CH 2 CHF-Ph-F CH 3 O-Ph-CH 2 CHF-Ph-F
【００６４】実施例４ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4,4'- ビス( トリフルオロメチ
ル) ベンジルフェニルケトンを6.64g(0.02mol)用いる以
外は実施例１と同様に反応を行い、1-フルオロ-1,2- ビ
ス(4- トリフルオロメチルフェニル) エタンを5.31g
（収率79％) 得た。 CF3-Ph-CH2CHF-Ph-CF3 Example 4 In place of the 4,4'-di (n-propyl) benzyl phenyl ketone used in Example 1, 4,64'-bis (trifluoromethyl) benzyl phenyl ketone was added at 6.64 g (0.02 mol). ) The reaction was performed in the same manner as in Example 1 except that 5.31 g of 1-fluoro-1,2-bis (4-trifluoromethylphenyl) ethane was used.
(Yield 79%) was obtained. CF 3 -Ph-CH 2 CHF-Ph-CF 3
【００６５】本化合物の分析結果を以下に示す。 ＭＳ m/e 336(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 336 (M + ) IR 1230cm -1 (CF)
【００６６】実施例４と同様にして、以下の化合物を得
ることができる。 CF3O-Ph-CH2CHF-Ph-CF3 CF3-Ph-CH2CHF-Ph-CH3 CF3-Ph-CH2CHF-Ph-OCF3 n-C3F7-Ph-CH2CHF-Ph-C3F7(n) CF3-C2H4-Ph-CH2CHF-Ph-C2H4-CF3 CF3-C2H4O-Ph-CH2CHF-Ph-OC2H4-CF3 CF3O-C2H4-Ph-CH2CHF-Ph-C2H4-OCF3 The following compounds can be obtained in the same manner as in Example 4. CF 3 O-Ph-CH 2 CHF-Ph-CF 3 CF 3 -Ph-CH 2 CHF-Ph-CH 3 CF 3 -Ph-CH 2 CHF-Ph-OCF 3 nC 3 F 7 -Ph-CH 2 CHF -Ph-C 3 F 7 (n) CF 3 -C 2 H 4 -Ph-CH 2 CHF-Ph-C 2 H 4 -CF 3 CF 3 -C 2 H 4 O-Ph-CH 2 CHF-Ph- OC 2 H 4 -CF 3 CF 3 OC 2 H 4 -Ph-CH 2 CHF-Ph-C 2 H 4 -OCF 3
【００６７】実施例５ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4-シアノベンジル-4-n- プロピ
ルフェニルケトンを5.26g(0.02mol)用いる以外は実施例
１と同様に反応を行い、1-フルオロ-1-(4-n-プロピルフ
ェニル)-2-(4-シアノフェニル) エタンを4.10g （収率7
8％) 得た。 NC-Ph-CH2CHF-Ph-C3H7(n)Example 5 Instead of the 4,4'-di (n-propyl) benzyl phenyl ketone used in Example 1, 5.26 g (0.02 mol) of 4-cyanobenzyl-4-n-propyl phenyl ketone was used. Other than that, the reaction was performed in the same manner as in Example 1 to obtain 4.10 g of 1-fluoro-1- (4-n-propylphenyl) -2- (4-cyanophenyl) ethane (yield 7
8%) obtained. NC-Ph-CH 2 CHF-Ph-C 3 H 7 (n)
【００６８】本化合物の分析結果を以下に示す。 ＭＳ m/e 267(M+) ＩＲ 1230cm-1(C-F),2230cm-1(C≡N)The analysis results of this compound are shown below. MS m / e 267 (M + ) IR 1230cm -1 (CF), 2230cm -1 (C≡N)
【００６９】実施例５と同様にして、以下の化合物を得
ることができる。 NC-Ph-CH2CHF-Ph-CH3 CH3-Ph-CH2CHF-Ph-CN NC-Ph-CH2CHF-Ph-OC3H7(n) n-C3H7-Ph-CH2CHF-Ph-CN NC-Ph-CH2CHF-Ph-C5H11(n) n-C5H11-Ph-CH2CHF-Ph-CNThe following compounds can be obtained in the same manner as in Example 5. NC-Ph-CH 2 CHF-Ph-CH 3 CH 3 -Ph-CH 2 CHF-Ph-CN NC-Ph-CH 2 CHF-Ph-OC 3 H 7 (n) nC 3 H 7 -Ph-CH 2 CHF-Ph-CN NC-Ph-CH 2 CHF-Ph-C 5 H 11 (n) nC 5 H 11 -Ph-CH 2 CHF-Ph-CN
【００７０】実施例６ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4-(n- プロピル) ベンジル-4-
(トランス-4- メチルシクロヘキシル) ケトンを5.12g
(0.02mol)用いる以外は実施例１と同様に反応を行い、1
-フルオロ-1-[4-(トランス-4- メチルシクロヘキシル)
フェニル]-2-(4-n- プロピルフェニル) エタンを3.77g
（収率73％) 得た。 n-C3H7-Ph-CH2CHF-Cy-CH3 Example 6 In place of 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 4- (n-propyl) benzyl-4-
5.12 g of (trans-4-methylcyclohexyl) ketone
(0.02 mol) was used and the reaction was carried out in the same manner as in Example 1,
-Fluoro-1- [4- (trans-4-methylcyclohexyl)
Phenyl] -2- (4-n-propylphenyl) ethane 3.77 g
(Yield 73%) was obtained. nC 3 H 7 -Ph-CH 2 CHF-Cy-CH 3
【００７１】[0071]
【化９】 [Chemical 9]
【００７２】本化合物の分析結果を以下に示す。 ＭＳ m/e 260(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 260 (M + ) IR 1230cm -1 (CF)
【００７３】実施例６と同様にして、以下の化合物を得
ることができる。 CH3-Ph-CH2CHF-Cy-CH3 n-C3H7-Cy-CH2CHF-Ph-CH3 n-C5H11-Ph-CH2CHF-Cy-C5H11(n) CH3O-Ph-CH2CHF-Cy-CH3 n-C3H7-Cy-CH2CHF-Ph-OC3H7(n) n-C3H7-Cy-CH2CHF-Ph-Cl n-C3H7-Cy-CH2CHF-Ph-CN n-C3H7-Cy-CH2CHF-Cy-C3H7(n)The following compounds can be obtained in the same manner as in Example 6. CH 3 -Ph-CH 2 CHF-Cy-CH 3 nC 3 H 7 -Cy-CH 2 CHF-Ph-CH 3 nC 5 H 11 -Ph-CH 2 CHF-Cy-C 5 H 11 (n) CH 3 O-Ph-CH 2 CHF-Cy-CH 3 nC 3 H 7 -Cy-CH 2 CHF-Ph-OC 3 H 7 (n) nC 3 H 7 -Cy-CH 2 CHF-Ph-Cl nC 3 H 7 -Cy-CH 2 CHF-Ph-CN nC 3 H 7 -Cy-CH 2 CHF-Cy-C 3 H 7 (n)
【００７４】実施例７ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4-(n- プロピル) ベンジル-4-
(5-メチルピリミジニル) ケトンを5.08g(0.02mol)用い
る以外は実施例１と同様に反応を行い、1-フルオロ-1-
(5-メチルピリミジニル)-2-(4-n- プロピルフェニル)
エタンを3.77g （収率73％) 得た。なお、以下の式中-P
y-は、2、5-ジ置換ピリミジニル基を示す。 CH3-Py-CH2CHF-Ph-C3H7(n)Example 7 In place of 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 4- (n-propyl) benzyl-4-
Reaction was carried out in the same manner as in Example 1 except that 5.08 g (0.02 mol) of (5-methylpyrimidinyl) ketone was used, and 1-fluoro-1-
(5-methylpyrimidinyl) -2- (4-n-propylphenyl)
3.77 g (73% yield) of ethane was obtained. In the formula below, -P
y- represents a 2,5-di-substituted pyrimidinyl group. CH 3 -Py-CH 2 CHF-Ph-C 3 H 7 (n)
【００７５】[0075]
【化１０】 [Chemical 10]
【００７６】本化合物の分析結果を以下に示す。 ＭＳ m/e 258(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 258 (M + ) IR 1230cm -1 (CF)
【００７７】CH3-Py-CH2CHF-Ph-CH3 n-C5H11-Ph-CH2CHF-Py-C5H11(n) CH3O-Py-CH2CHF-Ph-CH3 CH3-Py-CH2CHF-Ph-Cl CH3-Py-CH2CHF-Ph-CN n-C3H7-Py-CH2CHF-Cy-CH3 CH 3 -Py-CH 2 CHF-Ph-CH 3 nC 5 H 11 -Ph-CH 2 CHF-Py-C 5 H 11 (n) CH 3 O-Py-CH 2 CHF-Ph-CH 3 CH 3 -Py-CH 2 CHF-Ph-Cl CH 3 -Py-CH 2 CHF-Ph-CN nC 3 H 7 -Py-CH 2 CHF-Cy-CH 3
【００７８】実施例８ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4,4'- ジメチル-3,3'-ジフルオ
ロベンジルフェニルケトンを5.20g(0.02mol)用いる以外
は実施例１と同様に反応を行い、1-フルオロ-1,2- ビス
(3- フルオロ-4- メチルフェニル) エタンを4.03g （収
率77％) 得た。以下の式中-PhF- は、1,4-ジ置換-3- フ
ルオロフェニレン基を示す。 CH3-PhF-CH2CHF-PhF-CH3 Example 8 In place of the 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 5.20 g of 4,4'-dimethyl-3,3'-difluorobenzylphenylketone was used. 0.02 mol) was used and the reaction was performed in the same manner as in Example 1 to give 1-fluoro-1,2-bis
4.03 g (yield 77%) of (3-fluoro-4-methylphenyl) ethane was obtained. In the formula below, -PhF- represents a 1,4-disubstituted-3-fluorophenylene group. CH 3 -PhF-CH 2 CHF-PhF-CH 3
【００７９】[0079]
【化１１】 [Chemical 11]
【００８０】本化合物の分析結果を以下に示す。 ＭＳ m/e 246(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 246 (M + ) IR 1230cm -1 (CF)
【００８１】実施例８と同様にして、以下の化合物を得
ることができる。 n-C3H7-PhF-CH2CHF-PhF-C3H7(n) n-C3H7-PhF-CH2CHF-Ph-C3H7(n) CH3-PhF-CH2CHF-Ph-OCH3 n-C5H11-PhF-CH2CHF-Ph-Cl CF3-PhF-CH2CHF-Ph-CH3 The following compounds can be obtained in the same manner as in Example 8. nC 3 H 7 -PhF-CH 2 CHF-PhF-C 3 H 7 (n) nC 3 H 7 -PhF-CH 2 CHF-Ph-C 3 H 7 (n) CH 3 -PhF-CH 2 CHF-Ph -OCH 3 nC 5 H 11 -PhF-CH 2 CHF-Ph-Cl CF 3 -PhF-CH 2 CHF-Ph-CH 3
【００８２】実施例９ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4-(n- プロピル) ベンジル-4-
[4-( トランス-4- メチルシクロヘキシル) フェニル]
ケトンを6.64g(0.02mol)用いる以外は実施例１と同様に
反応を行い、1-フルオロ-1-[4-( トランス-4- メチルシ
クロヘキシル) フェニル]-2-(4-n- プロピルフェニル)
エタンを5.04g （収率75％）得た。 n-C3H7-Ph-CH2CHF-Ph-Cy-CH3 Example 9 In place of 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 4- (n-propyl) benzyl-4-
[4- (trans-4-methylcyclohexyl) phenyl]
The reaction was performed in the same manner as in Example 1 except that 6.64 g (0.02 mol) of ketone was used, and 1-fluoro-1- [4- (trans-4-methylcyclohexyl) phenyl] -2- (4-n-propylphenyl )
5.04 g (yield 75%) of ethane was obtained. nC 3 H 7 -Ph-CH 2 CHF-Ph-Cy-CH 3
【００８３】[0083]
【化１２】 [Chemical 12]
【００８４】本化合物の分析結果を以下に示す。 ＭＳ m/e 336(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 336 (M + ) IR 1230cm -1 (CF)
【００８５】実施例９と同様にして、以下の化合物を得
ることができる。 n-C3H7O-Ph-CH2CHF-Ph-Cy-C3H7(n) CH3-Cy-Ph-CH2CHF-Ph-CH3 n-C3H7-Cy-CH2CHF-Ph-Cy-C3H7(n) n-C5H11-Ph-Cy-CH2CHF-Ph-C5H11(n) CH3-Ph-CH2CHF-Ph-Cy-Cl n-C3H7O-Ph-CH2CHF-Cy-Ph-FThe following compounds can be obtained in the same manner as in Example 9. nC 3 H 7 O-Ph-CH 2 CHF-Ph-Cy-C 3 H 7 (n) CH 3 -Cy-Ph-CH 2 CHF-Ph-CH 3 nC 3 H 7 -Cy-CH 2 CHF-Ph -Cy-C 3 H 7 (n) nC 5 H 11 -Ph-Cy-CH 2 CHF-Ph-C 5 H 11 (n) CH 3 -Ph-CH 2 CHF-Ph-Cy-Cl nC 3 H 7 O-Ph-CH 2 CHF-Cy-Ph-F
【００８６】実施例１０ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4,4'- ビス[4-(トランス-4- メ
チルシクロヘキシル) フェニル] ベンジルフェニルケト
ンを7.68g(0.02mol)用いる以外は実施例１と同様に反応
を行い、1-フルオロ-1,2- ビス(4- トリフルオロメチル
フェニル) エタンを6.13g （収率79％)得た。 CH3-Cy-Ph-CH2CHF-Ph-Cy-CH3 Example 10 Instead of 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 4,4'-bis [4- (trans-4-methylcyclohexyl) phenyl] benzyl was used. The reaction was performed in the same manner as in Example 1 except that 7.68 g (0.02 mol) of phenyl ketone was used to obtain 6.13 g (yield 79%) of 1-fluoro-1,2-bis (4-trifluoromethylphenyl) ethane. It was CH 3 -Cy-Ph-CH 2 CHF-Ph-Cy-CH 3
【００８７】[0087]
【化１３】 [Chemical 13]
【００８８】本化合物の分析結果を以下に示す。 ＭＳ m/e 388(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 388 (M + ) IR 1230cm -1 (CF)
【００８９】実施例１０と同様にして、以下の化合物を
得ることができる。 CH3O-Ph-Cy-CH2CHF-Cy-Ph-OCH3 n-C3H7-Ph-Ph-CH2CHF-Ph-Ph-C3H7(n) CH3-Cy-Ph-CH2CHF-Ph-Cy-C3H7(n) n-C5H11-Ph-Cy-CH2CHF-Cy-Ph-F CH3-Cy-Ph-CH2CHF-Ph-Ph-CN CF3-Cy-Ph-CH2CHF-Cy-Ph-CH3 The following compounds can be obtained in the same manner as in Example 10. CH 3 O-Ph-Cy-CH 2 CHF-Cy-Ph-OCH 3 nC 3 H 7 -Ph-Ph-CH 2 CHF-Ph-Ph-C 3 H 7 (n) CH 3 -Cy-Ph-CH 2 CHF-Ph-Cy-C 3 H 7 (n) nC 5 H 11 -Ph-Cy-CH 2 CHF-Cy-Ph-F CH 3 -Cy-Ph-CH 2 CHF-Ph-Ph-CN CF 3 -Cy-Ph-CH 2 CHF-Cy-Ph-CH 3
【００９０】実施例１１ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4-(4- メチルフェネチル) ベン
ジルー4-n- プロピルフェニルケトンを7.12g(0.02mol)用
いる以外は実施例１と同様に反応を行い、1-フルオロ-1
-(4-n-プロピルフェニル)-2-[4-(4-メチルフェネチル)
フェニル] エタンを5.11g （収率71％)得た。 CH3-Ph-CH2CH2-Ph-CH2CHF-Ph-C3H7(n)Example 11 In place of the 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 7.12 g of 4- (4-methylphenethyl) benzyl-4-n-propylphenylketone was used. 0.02 mol) was used, and the reaction was performed in the same manner as in Example 1 to give 1-fluoro-1.
-(4-n-Propylphenyl) -2- [4- (4-methylphenethyl)
Phenyl] ethane (5.11 g, yield 71%) was obtained. CH 3 -Ph-CH 2 CH 2 -Ph-CH 2 CHF-Ph-C 3 H 7 (n)
【００９１】[0091]
【化１４】 [Chemical 14]
【００９２】本化合物の分析結果を以下に示す。 ＭＳ m/e 360(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 360 (M + ) IR 1230cm -1 (CF)
【００９３】実施例１１と同様にして、以下の化合物を
得ることができる。 CH3-Ph-CH2CH2-Ph-CH2CHF-Ph-C3H7(n) CH3O-Ph-CH2CH2-Ph-CH2CHF-Ph-OCH3 n-C3H7-Ph-CH2CH2-Ph-CH2CHF-Ph-Ph-CH3 CH3-Cy-CH2CH2-Ph-CH2CHF-Ph-C3H7(n) n-C5H11-Ph-CH2CH2-Cy-CH2CHF-Ph-F CH3-Cy-CH2CH2-Ph-CH2CHF-Ph-Ph-CNThe following compounds can be obtained in the same manner as in Example 11. CH 3 -Ph-CH 2 CH 2 -Ph-CH 2 CHF-Ph-C 3 H 7 (n) CH 3 O-Ph-CH 2 CH 2 -Ph-CH 2 CHF-Ph-OCH 3 nC 3 H 7 -Ph-CH 2 CH 2 -Ph- CH 2 CHF-Ph-Ph-CH 3 CH 3 -Cy-CH 2 CH 2 -Ph-CH 2 CHF-Ph-C 3 H 7 (n) nC 5 H 11 - Ph-CH 2 CH 2 -Cy-CH 2 CHF-Ph-F CH 3 -Cy-CH 2 CH 2 -Ph-CH 2 CHF-Ph-Ph-CN
【００９４】実施例１２ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、4-(2-P- トルイルエチニル) ベ
ンジルー4-n- プロピルフェニルケトンを7.04g(0.02mol)
用いる以外は実施例１と同様に反応を行い、1-フルオロ
-1-(4-n-プロピルフェニル)-2-[4-(2-P-トルイルエチニ
ル) フェニル] エタンを5.24g （収率74％) 得た。 CH3-Ph-C≡C-Ph-CH2CHF-Ph-C3H7(n)Example 12 4- (2-P-toluylethynyl) benzyl-4-n-propylphenylketone was replaced by 7.04 in place of 4,4'-di (n-propyl) benzylphenylketone used in Example 1. g (0.02mol)
The reaction was performed in the same manner as in Example 1 except that the 1-fluoro was used.
5.24 g (yield 74%) of -1- (4-n-propylphenyl) -2- [4- (2-P-toluylethynyl) phenyl] ethane was obtained. CH 3 -Ph-C ≡ C-Ph-CH 2 CHF-Ph-C 3 H 7 (n)
【００９５】[0095]
【化１５】 [Chemical 15]
【００９６】本化合物の分析結果を以下に示す。 ＭＳ m/e 356(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 356 (M + ) IR 1230cm -1 (CF)
【００９７】実施例１２と同様にして、以下の化合物を
得ることができる。 CH3-Ph-C≡C-Ph-CH2CHF-Ph-C3H7(n) CH3O-Ph-C ≡C-Ph-CH2CHF-Ph-OCH3 n-C3H7-Ph-C ≡C-Ph-CH2CHF-Ph-Ph-CH3 CH3-Cy-C≡C-Ph-CH2CHF-Ph-C3H7(n) n-C5H11-Ph-C≡C-Cy-CH2CHF-Ph-F CH3-Cy-C≡C-Ph-CH2CHF-Ph-Ph-CNThe following compounds can be obtained in the same manner as in Example 12. CH 3 -Ph-C ≡ C-Ph-CH 2 CHF-Ph-C 3 H 7 (n) CH 3 O-Ph-C ≡ C-Ph-CH 2 CHF-Ph-OCH 3 nC 3 H 7 -Ph -C ≡ C-Ph-CH 2 CHF-Ph-Ph-CH 3 CH 3 -Cy-C ≡ C-Ph-CH 2 CHF-Ph-C 3 H 7 (n) nC 5 H 11 -Ph-C ≡ C-Cy-CH 2 CHF-Ph-F CH 3 -Cy-C≡C-Ph-CH 2 CHF-Ph-Ph-CN
【００９８】実施例１３ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、(4- メチルベンジルオキシ) ベ
ンジルー4-n- プロピルフェニルケトンを7.16g(0.02mol)
用いる以外は実施例１と同様に反応を行い、1-フルオロ
-1ー(4-n-プロピルフェニル)-2-[4-(4-メチルベンジルオ
キシ) フェニル] エタンを5.50g 収率76％) 得た。 CH3-Ph-CH2O-Ph-CH2CHF-Ph-C3H7(n)Example 13 Instead of the 4,4'-di (n-propyl) benzylphenylketone used in Example 1, 7.16 g (0.02 g) of (4-methylbenzyloxy) benzyl-4-n-propylphenylketone was used. mol)
The reaction was performed in the same manner as in Example 1 except that the 1-fluoro was used.
-5- (4-n-propylphenyl) -2- [4- (4-methylbenzyloxy) phenyl] ethane (5.50 g, yield 76%) was obtained. CH 3 -Ph-CH 2 O-Ph-CH 2 CHF-Ph-C 3 H 7 (n)
【００９９】[0099]
【化１６】 [Chemical 16]
【０１００】本化合物の分析結果を以下に示す。 ＭＳ m/e 362(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 362 (M + ) IR 1230cm -1 (CF)
【０１０１】実施例１３と同様にして、以下の化合物を
得ることができる。 CH3-Ph-CH2O-Ph-CH2CHF-Ph-C3H7(n) CH3-Ph-OCH2-Ph-CH2CHF-Ph-C3H7(n) CH3O-Ph-CH2O-Ph-CH2CHF-Ph-OCH3 n-C3H7-Ph-CH2O-Ph-CH2CHF-Ph-Ph-CH3 CH3-Cy-CH2O-Ph-CH2CHF-Ph-C3H7(n) n-C5H11-Ph-CH2O-Cy-CH2CHF-Ph-F CH3-Cy-CH2O-Ph-CH2CHF-Ph-Ph-CNThe following compounds can be obtained in the same manner as in Example 13. CH 3 -Ph-CH 2 O-Ph-CH 2 CHF-Ph-C 3 H 7 (n) CH 3 -Ph-OCH 2 -Ph-CH 2 CHF-Ph-C 3 H 7 (n) CH 3 O -Ph-CH 2 O-Ph-CH 2 CHF-Ph-OCH 3 nC 3 H 7 -Ph-CH 2 O-Ph-CH 2 CHF-Ph-Ph-CH 3 CH 3 -Cy-CH 2 O-Ph -CH 2 CHF-Ph-C 3 H 7 (n) nC 5 H 11 -Ph-CH 2 O-Cy-CH 2 CHF-Ph-F CH 3 -Cy-CH 2 O-Ph-CH 2 CHF-Ph -Ph-CN
【０１０２】実施例１４ 実施例１で用いた4,4'- ジ(n- プロピル) ベンジルフェ
ニルケトンのかわりに、(4- メチルベンゾイルオキシ)
ベンジルー4-n- プロピルフェニルケトンを7.44g(0.02mo
l)用いる以外は実施例１と同様に反応を行い、1-フルオ
ロ-1-(4-n-プロピルフェニル)-2-[4-(4-メチルベンゾイ
ルオキシ) フェニル] エタンを5.64g （収率75％) 得
た。 CH3-Ph-COO-Ph-CH2CHF-Ph-C3H7(n)Example 14 Instead of the 4,4'-di (n-propyl) benzylphenyl ketone used in Example 1, (4-methylbenzoyloxy) was used.
7.44 g (0.02mo) of benzyl-4-n-propylphenylketone
l) The reaction was performed in the same manner as in Example 1 except for using 1-fluoro-1- (4-n-propylphenyl) -2- [4- (4-methylbenzoyloxy) phenyl] ethane (5.64 g, yield). (75%) obtained. CH 3 -Ph-COO-Ph-CH 2 CHF-Ph-C 3 H 7 (n)
【０１０３】[0103]
【化１７】 [Chemical 17]
【０１０４】本化合物の分析結果を以下に示す。 ＭＳ m/e 376(M+) ＩＲ 1230cm-1(C-F)The analysis results of this compound are shown below. MS m / e 376 (M + ) IR 1230cm -1 (CF)
【０１０５】実施例１４と同様にして、以下の化合物を
得ることができる。 CH3-Ph-COO-Ph-CH2CHF-Ph-C3H7(n) CH3-Ph-OCO-Ph-CH2CHF-Ph-C3H7(n) CH3O-Ph-COO-Ph-CH2CHF-Ph-OCH3 n-C3H7-Ph-COO-Ph-CH2CHF-Ph-Ph-CH3 CH3-Cy-COO-Ph-CH2CHF-Ph-C3H7(n) n-C5H11-Ph-COO-Cy-CH2CHF-Ph-F CH3-Cy-COO-Ph-CH2CHF-Ph-Ph-CNThe following compounds can be obtained in the same manner as in Example 14. CH 3 -Ph-COO-Ph-CH 2 CHF-Ph-C 3 H 7 (n) CH 3 -Ph-OCO-Ph-CH 2 CHF-Ph-C 3 H 7 (n) CH 3 O-Ph- COO-Ph-CH 2 CHF-Ph-OCH 3 nC 3 H 7 -Ph-COO-Ph-CH 2 CHF-Ph-Ph-CH 3 CH 3 -Cy-COO-Ph-CH 2 CHF-Ph-C 3 H 7 (n) nC 5 H 11 -Ph-COO-Cy-CH 2 CHF-Ph-F CH 3 -Cy-COO-Ph-CH 2 CHF-Ph-Ph-CN
【０１０６】実施例１５ メルク社製液晶組成物「ZLI-1565」97.5Wt％に、本発明
の実施例１の化合物を2.5wt％加えて液晶組成物とし
た。この粘度を調べたところ、従来例（メルク社製液晶
組成物「ZLI-1565」のみ）に比較して、粘度が低下し
た。この粘度の低下は、類似構造を有するジフルオロス
チルベンタイプの液晶を添加した場合とほぼ同じ程度で
あり、紫外線に対する劣化は、ジフルオロスチルベンタ
イプの液晶よりも少ないものであった。Example 15 2.5 wt% of the compound of Example 1 of the present invention was added to 97.5 Wt% of the liquid crystal composition "ZLI-1565" manufactured by Merck & Co., Inc. to give a liquid crystal composition. When the viscosity was examined, the viscosity was lower than that of the conventional example (only the liquid crystal composition "ZLI-1565" manufactured by Merck & Co., Inc.). This decrease in viscosity was almost the same as when the difluorostilbene type liquid crystal having a similar structure was added, and the deterioration with respect to ultraviolet rays was less than that of the difluorostilbene type liquid crystal.
【０１０７】[0107]
【発明の効果】本発明の一般式(1) R1-(A1)m-Y1-A2-CH2CHF-A3-Y2-(A4)n-R2 （A1〜A4、R1、R2、Y1、Y2、m 、n については前記の意
味を持つ）で示される化合物は、粘性が低く、液晶組成
物として用いることにより、少量の添加でも応答速度が
向上するものであり、低電圧駆動、高デューティ駆動、
広温度域動作等が可能になる。The general formula (1) R 1- (A 1 ) m -Y 1 -A 2 -CH 2 CHF-A 3 -Y 2- (A 4 ) n -R 2 (A 1 ~ The compounds represented by A 4 , R 1 , R 2 , Y 1 , Y 2 , m, and n have the above-mentioned meanings) and have a low viscosity. Is a low voltage drive, high duty drive,
Wide temperature range operation is possible.
【０１０８】また、紫外線等に対する耐久性もジフルオ
ロスチルベンタイプの液晶よりも高く、その低粘性の特
徴を充分活かすことができる。Further, the durability against ultraviolet rays and the like is higher than that of the difluorostilbene type liquid crystal, and the characteristic of its low viscosity can be fully utilized.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 69/75 Ａ 9279−4Ｈ Ｄ 9279−4Ｈ 69/757 Ｃ 9279−4Ｈ 69/773 9279−4Ｈ 69/84 9279−4Ｈ 69/94 9279−4Ｈ 255/46 6917−4Ｈ 255/50 6917−4Ｈ 255/54 6917−4Ｈ Ｃ０７Ｄ 239/26 7038−4Ｃ Ｃ０９Ｋ 19/14 7457−4Ｈ 19/16 7457−4Ｈ 19/18 7457−4Ｈ 19/20 7457−4Ｈ 19/30 7457−4Ｈ 19/34 7457−4Ｈ Ｇ０２Ｆ 1/13 ５００ (72)発明者 宮島 隆 神奈川県横浜市神奈川区羽沢町1150番地 旭硝子株式会社中央研究所内 (72)発明者 高 英昌 神奈川県横浜市神奈川区羽沢町松原1160番 地 エイ・ジー・テクノロジー株式会社内 (72)発明者 町田 勝利 神奈川県高座郡寒川町岡田４−16−31─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI Technical display location C07C 69/75 A 9279-4H D 9279-4H 69/757 C 9279-4H 69/773 9279-4H 69/84 9279-4H 69/94 9279-4H 255/46 6917-4H 255/50 6917-4H 255/54 6917-4H C07D 239/26 7038-4C C09K 19/14 7457-4H 19/16 7457-4H 19/18 7457-4H 19/20 7457-4H 19/30 7457-4H 19/34 7457-4H G02F 1/13 500 (72) Inventor Takashi Miyajima 1150 Hazawa-machi, Kanagawa-ku, Yokohama-shi, Kanagawa Asahi Glass Co., Ltd. Chuo In the laboratory (72) Hidemasa Taka Taka 1160 Matsubara, Hazawa-machi, Kanagawa-ku, Yokohama, Kanagawa Pref.A-G Technology Co., Ltd. (72) Inventor, Masaru Machida 4-16-31 Okada, Samukawa-cho, Takaza-gun, Kanagawa
Claims (3)
シクロヘキシレン基または1,4-ジ置換フェニレン基であ
り、これらの基は夫々非置換であるかあるいは置換基と
して１個もしくは２個以上のハロゲン、シアノ基を有し
ていてもよく、これらの基中に存在する１個もしくは２
個以上のCH基は窒素原子に置換されていてもよく、Y1、
Y2は相互に独立して-COO-,-OCO-,-C≡C-,-CH2CH2-,-OCH
2-,-CH2O-または単結合を示し、m,n は 0または 1を示
し、R1及びR2は相互に独立して炭素数 1〜10のアルキル
基、ハロゲン、シアノ基を示し、アルキル基の場合に
は、炭素−炭素結合間あるいはこの基と環との間の炭素
−炭素結合間に酸素原子が挿入されてもよく、また、そ
の炭素−炭素結合の一部が二重結合にされていてもよ
く、また、その１個の-CH2- 基がカルボニル基に置換さ
れていてもよく、また、その基中の水素原子の一部もし
くは全てがフッ素原子で置換されていてもよい）で表さ
れることを特徴とするモノフルオロアルカン誘導体化合
物。1. General formula (1) R 1- (A 1 ) m -Y 1 -A 2 -CH 2 CHF-A 3 -Y 2- (A 4 ) n -R 2 (wherein A 1 ~ A 4 is, independently of each other, a trans-1,4-di-substituted cyclohexylene group or a 1,4-di-substituted phenylene group, each of which is unsubstituted or has 1 or 2 substituents. It may have the above halogen or cyano group, and one or two existing in these groups
One or more CH groups may be substituted with a nitrogen atom, Y 1 ,
Y 2 is independently of each other -COO-,-OCO-,-C≡C-,-CH 2 CH 2 -,-OCH
2- , -CH 2 O- or a single bond, m, n are 0 or 1, R 1 and R 2 are each independently a C 1-10 alkyl group, a halogen, a cyano group. In the case of an alkyl group, an oxygen atom may be inserted between the carbon-carbon bond or between the carbon-carbon bond between this group and the ring, and a part of the carbon-carbon bond has a double bond. It may be a bond, or one of the —CH 2 — groups may be substituted with a carbonyl group, and some or all of the hydrogen atoms in the group may be substituted with a fluorine atom. A monofluoroalkane derivative compound represented by the formula:
を示す）で表されることを特徴とする請求項１のモノフ
ルオロアルカン誘導体化合物。2. General formula (2) R 1 -A 2 -CH 2 CHF-A 3 -R 2 (In the formula, A 2 , A 3 , R 1 and R 2 are the same as above.) The monofluoroalkane derivative compound according to claim 1, which is represented by:
ルカン誘導体化合物を含有することを特徴とする液晶組
成物。3. A liquid crystal composition comprising the monofluoroalkane derivative compound according to claim 1 or 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3357302A JPH05170679A (en) | 1991-12-25 | 1991-12-25 | Monofluoroalkane derivative and liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3357302A JPH05170679A (en) | 1991-12-25 | 1991-12-25 | Monofluoroalkane derivative and liquid crystal composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05170679A true JPH05170679A (en) | 1993-07-09 |
Family
ID=18453429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3357302A Withdrawn JPH05170679A (en) | 1991-12-25 | 1991-12-25 | Monofluoroalkane derivative and liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05170679A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002080413A (en) * | 2000-09-01 | 2002-03-19 | Seimi Chem Co Ltd | Optically active acetylene derivative, liquid crystal composition, and liquid crystal optoelecronic device |
| WO2002062921A1 (en) * | 2001-02-08 | 2002-08-15 | Seimi Chemical Co., Ltd. | Liquid-crystal composition containing optically active compound and liquid-crystal electrooptic element |
-
1991
- 1991-12-25 JP JP3357302A patent/JPH05170679A/en not_active Withdrawn
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002080413A (en) * | 2000-09-01 | 2002-03-19 | Seimi Chem Co Ltd | Optically active acetylene derivative, liquid crystal composition, and liquid crystal optoelecronic device |
| WO2002062921A1 (en) * | 2001-02-08 | 2002-08-15 | Seimi Chemical Co., Ltd. | Liquid-crystal composition containing optically active compound and liquid-crystal electrooptic element |
| EP1650284A2 (en) * | 2001-02-08 | 2006-04-26 | Seimi Chemical Co., Ltd. | Liquid crystal composition containing an optical active compound and liquid crystal electro-optical element |
| EP1650286A2 (en) * | 2001-02-08 | 2006-04-26 | Seimi Chemical Co., Ltd. | Liquid crystal composition containing an optically active compound and liquid crystal electro-optical element |
| EP1650285A2 (en) * | 2001-02-08 | 2006-04-26 | Seimi Chemical Co., Ltd. | Liquid crystal composition containing an optically active compound and liquid crystal electro-optical element |
| EP1650285A3 (en) * | 2001-02-08 | 2006-05-03 | Seimi Chemical Co., Ltd. | Liquid crystal composition containing an optically active compound and liquid crystal electro-optical element |
| EP1650286A3 (en) * | 2001-02-08 | 2006-05-17 | Seimi Chemical Co., Ltd. | Liquid crystal composition containing an optically active compound and liquid crystal electro-optical element |
| EP1650284A3 (en) * | 2001-02-08 | 2006-05-17 | Seimi Chemical Co., Ltd. | Liquid crystal composition containing an optical active compound and liquid crystal electro-optical element |
| US7108895B2 (en) | 2001-02-08 | 2006-09-19 | Seimi Chemical Co., Ltd. | Liquid crystal composition containing an optically active compound and liquid crystal electro-optical element |
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