CN101294079A - 液晶化合物 - Google Patents
液晶化合物 Download PDFInfo
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- CN101294079A CN101294079A CNA200810109441XA CN200810109441A CN101294079A CN 101294079 A CN101294079 A CN 101294079A CN A200810109441X A CNA200810109441X A CN A200810109441XA CN 200810109441 A CN200810109441 A CN 200810109441A CN 101294079 A CN101294079 A CN 101294079A
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
- Pyrane Compounds (AREA)
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及结构式(I)的液晶化合物,其中R1,R2,A1,A2,A3,A4,Z1,Z2,Z3,a,b和c具有在权利要求1中给出的意义,和涉及包括结构式(I)的至少一种化合物的液晶介质,和涉及含有这一类型的液晶介质的电光学显示器。
Description
本申请是中国发明专利申请No.200380104414.9的分案申请,其申请日为2003年11月17日,优先权日为2002年11月27日。
本发明涉及液晶化合物和涉及液晶介质,涉及它们用于电光学应用中的用途,和涉及含有该介质的显示器。
液晶主要用作显示设备中的电介质,因为此类物质的光学性能能够通过所施加的电压来改变。以液晶为基础的电光学设备是本领域技术人员所熟知的并且是以各种效应为基础的。此类设备的例子是具有动态散射的池,DAP(校直排列相的变形)池,宾/主池,具有扭曲向列结构的TN池,STN(超扭曲向列)池,SBE(超双折射效应)池和OMI(光学模式干涉)池。最普通的显示器是以Schadt-Helfrich效应为基础的并具有扭曲向列结构。
液晶材料必须具有良好的化学和热稳定性和对电场和电磁辐射的良好稳定性。此外,液晶材料应该具有低粘度和产生短的寻址时间,低的阈电压和在池中的高对比度。
它们还在通常操作温度下即在高于和低于室温的最宽可能范围中具有合适的介相(mesophase),例如上述池的向列或胆甾型介相。因为液晶一般作为几种组分的混合物来使用,重要的是这些组分彼此容易混溶。其它性能,如导电性、介电各向异性和光学各向异性,必须满足取决于池类型和应用领域的各种要求。例如,具有扭曲向列型结构的池的材料应该具有正的介电各向异性和低的导电性。
例如,对于有集成非线性元件用于转换各自像素的矩阵液晶显示器(MLC显示器)而言,具有大的正性介电各向异性,宽的向列相,较低的双折射率,非常高的电阻率,良好的UV和温度稳定性和低的蒸汽压的介质是所需要的。
这一类型的矩阵液晶显示器是已知的。可用于各自像素的各自转换的非线性元件是例如有源元件(即晶体管)。因此使用术语“有源矩阵”,其中在两种类型之间有区分:
1.在作为基片的硅晶片上的MOS(金属氧化物半导体)或其它二极管。
2.在作为基片的玻璃板上的薄膜晶体管(TFT)。
单晶硅作为基材的使用限制了显示尺寸,因为各种部分显示器(part-displays)的甚至模块组装将会在接合处导致诸多问题。
对于更具前景的类型2(它是优选的),所利用的电光学效应通常是TN效应。在两种技术之间有区别:TFT包括化合物半导体,如CdSe,或以多晶或无定形硅为基础的TFT。在全世界范围内对后一技术进行了深入的研究工作。
TFT矩阵应用于显示器的一个玻璃板的内侧,而另一个玻璃板在其内侧上携带透明反电极。与像素电极的尺寸对比,TFT是非常小的并对图像几乎没有不利影响。这一技术也能够延伸至全色可补偿型显示器,其中红光、绿光和蓝光过滤器的点阵是以过滤器元件与每一可转换的像素相对的方式来排列的。
TFT显示器通常作为在透射中有十字偏振镜的TN池来操作并且是背光的。
这里的术语MLC显示器覆盖了有集成非线性元件的任何矩阵显示器,即除了有源矩阵外,还有具有无源元件如变阻器或二极管(MIM=金属-绝缘体-金属)的显示器。
这一类型的MLC显示器特别适合于TV应用(例如便携式TV装置)或适合于计算机应用(移动电脑)和在汽车或飞机结构中的高信息显示器。除了与对比度和响应时间的角度依赖性有关的问题之外,在MLC显示器还遇到一些问题,归因于液晶混合物的不够高的电阻系数[TOGASHI,S.,SEKIGUCHI,K.,TANABE,H.,YAMAMOTO,E.,SORIMACHI,K.,TAJIMA,E.,WATANABE,H.,SHIMIZU,H.,Proc.Eurodisplay84,Sept.1984:A 210-288 Matrix LCD Controlled by Double StageDiode Rings,pp.141ff,Paris;STROMER,M.,Proc.Eurodisplay84,Sept.1984:Design of Thin Film Transistor for MatrixAddressing of Television Liquid Crystal Displays,pp.145ff,Paris]。随着电阻下降,MLC显示器的对比度会受损,也会发生图像后消除的问题。因为液晶混合物的电阻系数一般由于与显示器的内侧表面的相互作用而在MLC显示器的使用过程中下降,因此高(初始)电阻对于获得可接受的使用寿命是非常重要的。尤其对于低电压混合物,迄今不可能获得非常高的电阻率值。此外重要的是,电阻率将随着提高温度和在加热和/或UV曝光之后显示出最小可能的提高。现有技术的混合物的低温性能也是特别不利的。因此要求没有结晶和/或近晶相产生,甚至在低温下,而且粘度的温度依赖性是尽可能的低。现有技术的MLC显示器因此不满足今天的要求。
因此仍然需求不具有这些缺点,或仅仅在较低程度上具有这些缺点,在有大的工作温度范围,短的响应时间(甚至在低温下)和低的阈电压的同时,还有非常高的电阻系数的MLC显示器。
在TN(Schadt-Helfrich)池中,需要有利于在池中的下列优点的介质:
-延伸的向列相范围(尤其延伸至低温)
-在极低温度下(户外使用,汽车,航空飞行器)转换的能力
-对UV辐射有提高的耐受性(较长的使用寿命)
现有技术的介质无法在同时保持其它参数的同时还实现这些优点。
对于超扭曲(STN)池需要这样的介质,它允许有更大的多路转换性和/或较低的阈电压和/或较宽的向列相范围(尤其在低温下)。为此,有用的参数范围(澄清点、近晶-向列转变或熔点、粘度、介电参数、弹性参数)的进一步拓宽是迫切需要的。
本发明的一个目的是提供介质,尤其用于这一类型的MLC,IPS,TN或STN显示器,它不具有上述缺点或仅仅在较低程度上具有上述缺点,和优选同时具有非常高的电阻率值和低的阈电压。这一目的需要具有高的澄清点和低的旋转粘度的液晶化合物。
现已发现,如果使用本发明的液晶化合物则能够实现这一目的。
本发明因此涉及结构式I的液晶化合物:
其中
R1和R2各自独立地表示H,卤素,具有1-15个碳原子的卤代或未取代的烷基或烷氧基,其中,另外在这些基团中的一个或多个CH2基团可以各自独立地被-C≡C-,-CH=CH-,-O-,-CO-O-或-O-CO-替代,但要求O原子不直接彼此连接,其中基团R1和R2中的一个可以另外表示CN,OCN,SCN,NCS或SF5,
A1,A2,A3和A4各自独立地表示:
Z1,Z2和Z3各自独立地表示-CO-O-,-O-CO-,-CF2O-,-OCF2-,-CH2O-,-OCH2-,-CH2CH2-,-(CH2)4-,-C2F4-,-CH2CF2-,-CF2CH2-,-CF=CF-,-CH=CH-,-C≡C-或单键,和
a,b和c各自独立地表示0,1,2或3,其中a+b+c≤3。
本发明进一步涉及结构式I的化合物在液晶介质中的使用。
结构式I的化合物具有宽的应用范围。取决于取代基的选择,这些化合物能够用作主要构成液晶介质的基础材料;然而,还有可能添加结构式I的化合物到选自其它类型化合物中的液晶基础材料中,以便于例如改进这一类型的电介质的介电和/或光学各向异性,和/或以便于优化它的阈电压和/或它的粘度。
以纯净状态,结构式I的化合物是无色的和在有利地为电光学应用所确定的温度范围内形成液晶介相。尤其,根据本发明的化合物突出表现于它们的宽向列相范围。在液晶混合物中,根据本发明的物质会抑制近晶相和导致在低温贮存稳定性上的显著改进。它们是对化学、热和光是稳定的。
本发明尤其涉及其中R1是烷基或链烯基,和R2是卤素或OCF3的结构式I的化合物。卤素优选是F,还有Cl。
特别优选的是其中a=0,还有a=1的结构式I的化合物。Z1,Z2和/或Z3优选表示单键,此外-CF2O-,-OCF2-,-C2F4-,-CH2O-,-OCH2-或-COO-。
特别优选的是结构式I A的化合物:
其中
a和b各自表示0,1或2和a+b=1或2。优选,a=1和b=0或a=0和b=1。优选,L1=F和L2=H或氟,尤其L1=L2=氟。
R1优选表示烷基,烷氧基,链烯基或链烯基氧基。R2优选表示F,Cl,OCF3,OCHF2,OCHFCF3,OCF2CHFCF3,CN,SF5,NCS或SCN,尤其F或OCF3,和R1优选表示直链烷基或链烯基。L1和L2各自独立地表示H或F。特别优选的是其中X=L1=L2=氟,此外X=OCF3和L1=L2=F的化合物。
结构式I的特别优选的化合物是结构式I1至I31的化合物:
其中R1具有以上给出的意义。X具有R2的意义。
结构式I的化合物能够通过让外消旋物例如通过手性HPLC柱而非常容易地分离成对映异构体。本发明因此涉及外消旋体和对映异构体形式的结构式I的化合物。
结构式I的化合物是通过在文献中(例如在标准著作如Houben-Weyl,Methoden der organischen Chemie[有机化学方法],Georg-Thieme-Verlag,Stuttgart中)描述的本身已知的方法制备的,准确地说在已知的和适合于该反应的反应条件下制备的。还可以使用本身已知的,但没有在这里详细描述的各种变型。
结构式I的化合物例如能够如下制备:
反应流程1
反应流程2
反应流程3
反应流程4
反应流程5
(L1和L2:H或F)
本发明还涉及含有这一类型的介质的电光学显示器(尤其具有两个平面平行外板(它们与框架一起形成池),在外板上用于转换各自像素的集成非线性元件,和位于池中的具有正介电各向异性和高电阻率的向列液晶混合物的STN或MLC显示器,),和涉及这些介质在电光学应用中的用途。
根据本发明的液晶混合物能够使有效参数范围有显著拓宽。
澄清点、在低温下的粘度、热和UV稳定性以及介电各向异性的可实现的组合远远优于现有技术的先前材料。
对于高澄清点、在低温下的向列相和高Δε的要求迄今只能在不足够的程度上满足。虽然液晶混合物如MS99295(Merck KGaA,Darmstadt,Germany)具有相当的澄清点和低温稳定性,但是它们具有较高的Δn值和约≥1.7V的较高阈电压。
其它混合物体系具有可比的粘度和Δε值,但仅仅具有在60℃的范围内的澄清点。
根据本发明的液晶混合物,在低至-20℃和优选低至-30℃,特别优选低至-40℃保持向列相的同时,能够使澄清点高于80℃,优选高于90℃,特别优选高于100℃,同时达到≥4,优选≥6的介电各向异性值Δε,和高的电阻率值,从而获得优异的STN和MLC显示器。尤其,混合物以低的操作电压为特征。TN阈电压低于1.5V,优选低于1.3V。
不用说,通过根据本发明的混合物的各组分的合适选择,还有可能在较高阈电压下实现较高澄清点(例如高于110℃)或在较低阈电压下实现较低澄清点,而其它理想性能得以保留。在仅仅稍微相应提高的粘度下,同样有可能获得具有较大Δε和因此较低阈电压的混合物。根据本发明的MLC显示器优选在第一Gooch和Tarry透射最小值下操作[C.H.Gooch和H.A.Tarry,Electron.Lett.10,2-4,1974;C.H.Gooch和H.A.Tarry,Appl.Phys.,Vol.8,1575-1584,1975],其中除了特别理想的电光学性能例如特征线的高陡度和对比度的低角度依赖性(德国专利30 22 818)之外,较低的介电各向异性将在第二最小值下在与类似显示器中相同的阈电压下是足够的。与混合物包括氰基化合物的情况相比,这使得通过使用本发明的混合物在第一最小值下可达到高得多的电阻率值。通过各自组分和它们的重量比例的合适选择,本领域中的技术人员能够使用简单的常规方法设定为MLC显示器的预定层厚度所需要的双折射率。
在20℃下流动粘度v 20优选是<60mm2·s-1,特别优选<50mm2·s-1。向列相范围优选是至少90°,尤其至少100°。这一范围优选从至少-30°延伸至+80°。在20℃下的旋转粘度γ1优选是<200mPa·s,特别优选<180mPa·s,尤其<160mPa·s。
电容保持率(HR)[S.Matsumoto等人,Liquid Crystals 5,1320(1989);K.Niwa等人,Proc.SID Conference,San Francisco,June 1984,p.304(1984);G.Weber等人,Liquid Crystals 5,1381(1989)]的测量结果已经表明,与没有结构式I的化合物但包括结构式的氰基苯基环己烷类或结构式的酯类的类似混合物相比,包括结构式I的化合物的本发明混合物随着温度提高而显示出在HR上的较小下降。
根据本发明的混合物的UV稳定性也相当好,即它们在暴露于UV时显示了在HR上显著较小的下降。
根据本发明的介质优选是以结构式I的多种(优选两种、三种或更多种)化合物为基础的,即这些化合物的比例是5-95%,优选10-60%和特别优选在15-40%范围内。
能够用于本发明的介质中的结构式I-IX和它们的子结构式的各自化合物是已知的或它们能够与已知化合物类似地制备。
优选的实例在下面给出:
-介质优选包括结构式I的一种,两种或三种同系化合物,其中各同系物是以10%的最高量存在于混合物中。
-介质另外包括选自结构式II至IX中的一种或多种化合物:
其中各自基团具有以下意义:
R0表示正烷基,氧杂烷基,氟烷基,链烯基氧基或链烯基,各自具有至多9个碳原子,
X0表示F,Cl,具有至多7个碳原子的卤代烷基,卤代链烯基,卤代链烯基氧基或卤代烷氧基,
Z0表示-CH=CH-,-C2H4-,-(CH2)4-,-C2F4-,-CH2O-,-OCH2-,-CF=CF-,-CF2O-,-OCF2-或-COO-,
Y1,Y2,Y3和Y4各自独立地表示H或F,和
r是0或1。
结构式IV的化合物优选是
或
-介质优选包括下面结构式的一种或多种化合物:
和/或
其中R0和Y2具有以上给出的意义。
-介质优选包括选自H1至H19(n=1-7)中的化合物的一种,两种或三种,以及四种同系物:
-介质另外包括选自通式X至XV中的一种或多种化合物:
其中R0,X0,Y1,Y2,Y3和Y4各自独立地具有在权利要求8中给出的意义中的一个。X0优选表示F,Cl,CF3,OCF3或OCHF2。R0优选表示烷基,氧杂烷基,氟烷基,链烯基或链烯基氧基。
-结构式I至IX的化合物一起在全部混合物中的比例是至少50wt%。
-结构式I的化合物在全部混合物中的比例是至少5-50wt%。
-结构式II的化合物在全部混合物中的比例是至少3-40wt%。
-结构式II至IX的化合物在全部混合物中的比例是至少30-70wt%。
-介质包括结构式II、III、IV、V、VI、VII、VIII和/或IX的化合物。
-R0是具有2-7个碳原子的直链烷基或链烯基。
-介质基本上由结构式I至XV的化合物组成
-介质包括5-40wt%的结构式H17和/或H18的化合物。
-介质包括其它化合物,优选选自通式XVI至XX,
其中R0和X0具有上文给出的意义,以及1,4-亚苯基环可被CN、氯或氟取代。1,4-亚苯基环优选被氟原子单-或多-取代。
-介质包括其它化合物,优选选自通式RI至RIX
其中
R0表示正烷基,氧杂烷基,氟烷基,链烯基氧基或链烯基,各自具有至多9个碳原子,
d表示0,1或2,
Y1表示H或F,
alkyl或alkyl*各自独立地表示具有1-9个碳原子的直链或支链烷基,
alkenyl或alkenyl*各自独立地表示具有至多9个碳原子的直链或支链链烯基,
-介质优选包括以下结构式的一种或多种化合物:
其中n和m各自表示1-9的整数。
-I:(II+III+IV+V+VI+VII+VIII+IX)重量比优选是1∶10至10∶1.
-介质基本上由选自通式I至XV的化合物组成。
现已发现,与普通液晶材料,尤其与结构式II、III、IV、V、VI、VII、VIII或IX的一种或多种化合物,相混合的甚至较小比例的结构式I的化合物,将导致阈电压的显著降低和低的双折射率值,同时观察到有低近晶-向列相转变温度的宽向列相,改进了贮存稳定性。结构式I至IX的化合物是无色的,稳定的并且彼此之间以及与其它液晶材料之间容易混溶。
该术语“烷基”或“烷基*”包括具有1-9个碳原子的直链和支链烷基,特别是直链基团甲基,乙基,丙基,丁基,戊基,己基和庚基。具有2-5个碳原子的基团一般是优选的。
该术语“链烯基”或“链烯基*”包括具有至多9个碳原子的直链和支链链烯基,尤其是直链基团。特别优选的链烯基基团是C2-C7-1E-链烯基,C4-C7-3E-链烯基,C5-C7-4-链烯基,C6-C7-5-链烯基和C7-6-链烯基,尤其C2-C7-1E-链烯基,C4-C7-3E-链烯基和C5-C7-4-链烯基。优选的链烯基基团的例子是乙烯基,1E-丙烯基,1E-丁烯基,1E-戊烯基,1E-己烯基,1E-庚烯基,3-丁烯基,3E-戊烯基,3E-己烯基,3E-庚烯基,4-戊烯基,4Z-己烯基,4E-己烯基,4Z-庚烯基,5-己烯基,6-庚烯基等等。具有至多5个碳原子的基团一般是优选的。
该术语“氟烷基”优选包括具有末端氟的直链基团,即氟甲基,2-氟乙基,3-氟丙基,4-氟丁基,5-氟戊基,6-氟己基和7-氟庚基。然而,氟的其它位置没有排除。
该术语“氧杂烷基”优选包括通式CnH2n+1-O-(CH2)m的直链基团,其中n和m各自彼此独立地表示1到6。优选,n=1和m表示1到6。
通过R0和X0的意义的合适选择,寻址时间、阈电压、透射特征线的陡度等能够以所需方式改进。例如,1E-链烯基,3E-链烯基,2E-链烯基氧基等会导致更短的寻址时间,改进的向列倾向和更高的弹性常数k33(弯曲)和k11(倾斜)的比率,与烷基或烷氧基的情况相比。而与烷基或烷氧基的情况相比,4-链烯基,3-链烯基等一般得到更低的阈电压和更小的k33/k11值。
与单个共价键相比,在Z1和/或Z2中的-CH2CH2-基团一般会导致更高的k33/k11值。更高的k33/k11值有利于例如在有90°扭曲的TN池中的较平缓透射特征线(为了获得灰色调)和在STN、SBE和OMI池中更陡的透射特征线(更大的多路转换性),反之亦然。
结构式I和II+III+IV+V+VI+VII+VIII+IX的化合物的最佳混合比主要取决于所需性能、结构式I、II、III、IV、V、VI、VII、VIII和/或IX的组分的选择、和可存在的任何其它组分的选择。在以上给定的范围内,合适混合比能够根据具体情况容易地确定。
结构式I至XV的化合物在本发明的混合物中的总量不是关键的。该混合物因此可包括为了各种性能的优化目的的一种或多种其它组分。然而,对于寻址时间和阈电压所观察的影响一般越大,结构式I至XV的化合物的总浓度越高。
在特别优选的实施方案中,根据本发明的介质包括结构式II至IX(优选II和/或III)的化合物,其中X0表示OCF3,OCHF2,F,OCH=CF2,OCF=CF2,OCF2CHFCF3或OCF2-CF2H。结构式I的化合物的有益的协同效果导致了特别理想的性能。
本发明的MLC显示器从偏振镜、电极基板和表面处理的电极的构造对应于这一类型显示器的普通构造。术语“普通构造”是在这里广义描绘的并还包括MLC显示器的全部派生和改进形式,尤其包含了以poly-Si TFT或MIM为基础的矩阵显示元件。
然而在本发明的显示器和以扭曲向列池为基础的目前普通显示器之间的显著差异在于液晶层的液晶参数的选择。
根据本发明所使用的液晶混合物是按照本身常用的方式来制备的。一般,将所需量的的组分以较少量溶于构成主要成分的组分中,理想地在升高的温度下。还有可能将各组分在有机溶剂中,例如在丙酮、氯仿或甲醇中的溶液进行混合,和在彻底混合之后,再次例如通过蒸馏除去溶剂。
电介质也可包括本领域中技术人员已知的和在文献中描述的其它添加剂,如稳定性和抗氧化剂。例如能够添加0-15%的多色染料或手性掺杂剂。
C表示晶体相,S表示近晶相,SC表示近晶C相,SB表示近晶B相,N表示向列相和I表示各向同性相。
V10表示10%透射率(垂直于板表面的视角)的电压。ton表示接通时间和toff表示在对应于V10的值的2倍的操作电压下的关闭时间。Δn表示光学各向异性和no表示折射指数。Δε表示介电各向异性(Δε=ε||-ε⊥,其中ε||表示在与分子的纵轴平行方向上的介电常数和ε⊥表示垂直方向上的介电常数)。电光学性能数据是在20℃下在第一最小值(即在0.5μm的d·Δn值下)下在TN池中测量,除非另外特意指明。光学数据是在20℃下测量的,除非另作说明。
在本申请和在下面的实施例中,液晶化合物的结构是利用首字母缩写词来表示,根据下面的表A和B来转变成化学式。全部基团CnH2n+1和CmH2m+1是分别具有n和m个碳原子的直链烷基,n和m各自独立地是1,2,3,4,5,6,7,8,9,10,11,12,13,14或15。在表B中的代码是不言自明的。在表A中仅仅给出了母体结构的首字母缩写词。在各情况下,在母体结构的首字母缩写词之后接着是,被破折号分开的对于取代基R1,R2,L1和L2所给出的代码。
R1,R2,L1,L2 R1 R2 L1 L2
的代码
nm CnH2n+1 CmH2m+1 H H
nOm CnH2n+1 OCmH2m+1 H H
nO.m OCnH2n+1 CmH2m+1 H H
n CnH2n+1 CN H H
nN.F CnH2n+1 CN H F
nF CnH2n+1 F H H
nOF OCnH2n+1 F H H
nCl CnH2n+1 Cl H H
R1,R2,L1,L2 R1 R2 L1 L2
的代码
nF.F CnH2n+1 F H F
nF.F.F CnH2n+1 F F F
nCF3 CnH2n+1 CF3 H H
nOCF3 CnH2n+1 OCF3 H H
nOCF3.F CnH2n+1 OCF3 H F
nOCF2 CnH2n+1 OCHF2 H H
nS CnH2n+1 NCS H H
rVsN CrH2r+1-CH=CH-CsH2s- CN H H
rEsN CrH2r+1-O-C2H2s- CN H H
nAm CnH2n+1 COOCmH2m+1 H H
nOCCF2.F.F CnH2n+1 OCH2CF2H F F
优选的混合物组分在表A和B中给出,
表B:
表C
表C给出了一般以0.1-10wt%的量添加到本发明的化合物中的可能的掺杂剂。
表D
能够添加到例如本发明的混合物中的稳定剂是下面所提及的。
下面实施例用于解释本发明但不限制本发明。上下文中,百分数是重量百分数。全部温度是以摄氏度给出。m.p.表示熔点。cl.p.表示澄清点。此外,C=晶体状态,N=向列相,S=近晶相和I=各向同性相。在这些符号之间的数据表示转变温度。Δn表示光学各向异性(589nm,20℃),Δε表示介电各向异性(1kHz,20℃)。流动粘度v20(mm2/sec)是在20℃下测定的。旋转粘度γ1(mPa·s)同样是在20℃下测定的。
“常规后处理”是指,如果需要添加水,混合物用二氯甲烷、乙醚、甲基叔丁基醚或甲苯萃取,分相,干燥有机相和蒸发,然后产物由减压蒸馏或结晶和/或色谱分离法提纯。使用下面缩写:
n-BuLi 正丁基锂在正己烷中的1.6摩尔浓度溶液
DMAP 4-(二甲基氨基)吡啶
THF 四氢呋喃
DCC N,N’-二环己基碳二亚胺
LDA 二甲基胺化锂
RT 室温
实施例1
步骤1.1
B是与文献中类似地制备的。a)R.Bake r,A.L.Boyes,C.J.Swain,J.Chem.Soc.Perkin Trans.1,1990,1415-1421;b)H.Hagiwara,T.Okabe,H.Ono,V.P.Kamat,T.Hoshi,T.Suzuku,M.Ando,J.Chem.Soc.Perkin Trans.1,2002,895-900。
步骤1.2
将207mmol的BuLi(在己烷中15%)在-50℃下滴加到207mmol的1,4-二溴苯在250ml乙醚中的溶液中。然后在同一温度下滴加170mmol的B在50ml乙醚中的溶液,混合物进一步搅拌另外30分钟,然后回到0℃和进行常规水后处理。将粗产物(51g)溶于400ml的CH2Cl2中,和在-75℃下添加400mmol的三乙基硅烷。滴加400mmol的三氟化硼合乙醚,在此过程中温度不要升高到-70℃以上。混合物然后升至-10℃,使用饱和NaHCO3溶液进行水解,和然后进行常规水后处理。粗产物包括9∶1比率的顺/反异构体。产物在-20℃下从戊烷中重结晶。
步骤1.3
将73mmol的C溶于200ml的THF中和冷却至-70℃。首先滴加73mmol的BuLi(在己烷中15%),随后滴加73mmol的硼酸三甲基酯在50ml THF中的溶液。混合物升至-20℃,通过添加2N HCl调节至pH=2,然后进行水后处理。粗产物置于热庚烷中和在0℃下结晶。
步骤1.4
60mmol的D、300ml的甲苯、120mmol的NaOH,50ml的水和30ml的30%H2O2的混合物在45℃下搅拌2小时。混合物使用10%HCl调节至pH=2,然后进行水后处理。粗产物从庚烷中重结晶。
步骤1.5
22mmol的E在1.5g水润湿5%Pd/C存在下在100ml二甲苯中在5巴和130℃下氢化27.5小时。常规后处理得到无色油。
步骤1.6
17mmol的BuLi(在己烷中15%)在-70℃下添加到17mmol的2-三甲基甲硅烷基-1,3-二噻烷在75ml THF中的溶液中。混合物经4小时的时间升至0℃,然后再冷却至-70℃,将17mmol的F在25ml的THF中的溶液滴加进去,混合物然后升至室温,再搅拌18小时,进行常规水后处理。粗产物从庚烷中重结晶,得到无色晶体。
步骤1.7
6.27mmol的三氟甲烷磺酸在-20℃下滴加到6.12mmol的G在50mml的CH2Cl2中的溶液中。混合物经30分钟升至室温,然后冷却至-70℃。首先添加9.1mmol的3,4,5-三氟苯酚和10.1mmol的三乙基胺在20 l的CH2Cl2中的溶液,5分钟过后添加31mmol的三乙基胺三(氢氟酸盐)。在另外5分钟之后,以多个小份添加31.5mmol的DBH(1,3-二溴-5,5-二甲基乙内酰脲)的悬浮液,然后混合物在-70℃下另外搅拌1小时。反应混合物升至-10℃,然后倾倒在400ml的冰冷NaOH中。混合物进行常规水后处理,粗产物通过硅胶色谱分离(庚烷/甲苯3∶2)和在-70℃下从戊烷中结晶来提纯,得到无色晶体:C 35 N 66.31;Δn=0.0570;Δε=13.4。
类似地制备以下结构式的化合物:
R1 X L1 L2
H F H H
CH3F H H
C2H5F H H
n-C4H9 F H H
n-C5H11 F H H
n-C6H13 F H H
H F F H
CH3F F H
C2H5F F H
n-C3H7 F F H C 41 SB 51 N 95.9 I;
Δε=9.7;Δn=0.0688
n-C4H9 F F H C 31 SB 64 N 97.1 I;
Δε=9.3;Δn=0.0621
n-C5H11 F F H
n-C6H13 F F H
H F F F
CH3 F F F C 54 I;
Δε=14.8;Δn=0.0490
C2H5 F F F C 48 N(34.7) I;
Δε=14.1;Δn=0.0540
n-C3H7 F F F
n-C4H9 F F F C 43 N 66.1 I;
Δε=13.3;Δn=0.0590
n-C5H11 F F F C 39 N 75.3 I;
Δε=11.8;Δn=0.0568
n-C6H13 F F F
H Cl H H
CH3 Cl H H
C2H5 Cl H H
n-C3H7 Cl H H
n-C4H9 Cl H H
n-C5H11 Cl H H
n-C6H13 Cl H H
H Cl F H
CH3 Cl F H
R1 X L1 L2
C2H5 Cl F H
n-C3H7 Cl F H
n-C4H9 Cl F H
n-C5H11 Cl F H
n-C6H13 Cl F H
H Cl F F
CH3 Cl F F
C2H5 Cl F F
n-C3H7 Cl F F
n-C4H9 Cl F F
n-C5H11 Cl F F
n-C6H13 Cl F F
H OCF3 H H
CH3 OCF3 H H
C2H5 OCF3 H H
n-C3H7 OCF3 H H C -41 SB 123 N 129.3 I;
Δε=9.1;Δn=0.0780
n-C4H9 OCF3 H H C?-54 SB 129 I;
Δε=9.1;Δn=0.0689
n-C5H11 OCF3 H H
n-C6H13 OCF3 H H
H OCF3 F H
CH3 OCF3 F H
C2H5 OCF3 F H
n-C3H7 OCF3 F H SB 74 N 105.8 I;
Δε=11.7;Δn=0.0701
n-C4H9 OCF3 F H SB 81 N 105.8 I;
Δε=11.5;Δn=0.0623
n-C5H11 OCF3 F H
n-C6H13 OCF3 F H
H OCF3 F F
CH3 OCF3 F F
C2H5 OCF3 F F
n-C3H7 OCF3 F F
n-C4H9 OCF3 F F
R1 X L1 L2
n-C5H11 OCF3 F F
n-C6H13 OCF3 F F
H OCHF2 H H
CH3 OCHF2 H H
C2H5 OCHF2 H H
n-C3H7 OCHF2 H H
n-C4H9 OCHF2 H H
n-C5H11 OCHF2 H H
n-C6H13 OCHF2 H H
H OCHF2 F H
CH3 OCHF2 F H
C2H5 OCHF2 F H
n-C3H7 OCHF2 F H
n-C4H9 OCHF2 F H
n-C5H11 OCHF2 F H
n-C6H13 OCHF2 F H
H OCHF2 F F
CH3 OCHF2 F F
C2H5 OCHF2 F F
n-C3H7 OCHF2 F F
n-C4H9 OCHF2 F F
n-C5H11 OCHF2 F F
n-C6H13 OCHF2 F F
H OCHFCF3 H H
CH3 OCHFCF3 H H
C2H5 OCHFCF3 H H
n-C3H7 OCHFCF3 H H
n-C4H9 OCHFCF3 H H
n-C5H11 OCHFCF3 H H
n-C6H13 OCHFCF3 H H
H OCHFCF3 F H
CH3 OCHFCF3 F H
C2H5 OCHFCF3 F H
n-C3H7 OCHFCF3 F H
n-C4H9 OCHFCF3 F H
R1 X L1 L2
n-C5H11 OCHFCF3 F H
n-C6H13 OCHFCF3 F H
H OCHFCF3 F F
CH3 OCHFCF3 F F
C2H5 OCHFCF3 F F
n-C3H7 OCHFCF3 F F
n-C4H9 OCHFCF3 F F
n-C5H11 OCHFCF3 F F
n-C6H13 OCHFCF3 F F
H OCHFCF3 H H
CH3 OCHFCF3 H H
C2H5 OCHFCF3 H H
n-C3H7 OCHFCF3 H H
n-C4H9 OCHFCF3 H H
n-C5H11 OCHFCF3 H H
n-C6H13 OCHFCF3 H H
H OCHFCF3 F H
CH3 OCHFCF3 F H
C2H5 OCHFCF3 F H
n-C3H7 OCHFCF3 F H
n-C4H9 OCHFCF3 F H
n-C5H11 OCHFCF3 F H
n-C6H13 OCHFCF3 F H
H OCHFCF3 F F
CH3 OCHFCF3 F F
C2H5 OCHFCF3 F F
n-C3H7 OCHFCF3 F F
n-C4H9 OCHFCF3 F F
n-C5H11 OCHFCF3 F F
n-C6H13 OCHFCF3 F F
H OCF2CHFCF3 H H
CH3 OCF2CHFCF3 H H
C2H5 OCF2CHFCF3 H H
n-C3H7 OCF2CHFCF3 H H
n-C4H9 OCF2CHFCF3 H H
R1 X L1 L2
n-C5H11 OCF2CHFCF3 H H
n-C6H13 OCF2CHFCF3 H H
H OCF2CHFCF3 F H
CH3 OCF2CHFCF3 F H
C2H5 OCF2CHFCF3 F H
n-C3H7 OCF2CHFCF3 F H
n-C4H9 OCF2CHFCF3 F H
n-C5H11 OCF2CHFCF3 F H
n-C6H13 OCF2CHFCF3 F H
H OCF2CHFCF3 F F
CH3 OCF2CHFCF3 F F
C2H5 OCF2CHFCF3 F F
n-C3H7 OCF2CHFCF3 F F
n-C4H9 OCF2CHFCF3 F F
n-C5H11 OCF2CHFCF3 F F
n-C6H13 OCF2CHFCF3 F F
H NCS H H
CH3 NCS H H
C2H5 NCS H H
n-C3H7 NCS H H
n-C4H9 NCS H H
n-C5H11 NCS H H
n-C6H13 NCS H H
H NCS F H
CH3 NCS F H
C2H5 NCS F H
n-C3H7 NCS F H
n-C4H9 NCS F H
n-C5H11 NCS F H
n-C6H13 NCS F H
H NCS F F
CH3 NCS F F
C2H5 NCS F F
n-C3H7 NCS F F
n-C4H9 NCS F F
R1 X L1 L2
n-C5H11 NCS F F
n-C6H13 NCS F F
H C2F5 H H
CH3 C2F5 H H
C2H5 C2F5 H H
n-C3H7 C2F5 H H
n-C4H9 C2F5 H H
n-C5H11 C2F5 H H
n-C6H13 C2F5 H H
H C2F5 F H
CH3 C2F5 F H
C2H5 C2F5 F H
n-C3H7 C2F5 F H
n-C4H9 C2F5 F H
n-C5H11 C2F5 F H
n-C6H13 C2F5 F H
H C2F5 F F
CH3 C2F5 F F
C2H5 C2F5 F F
n-C3H7 C2F5 F F
n-C4H9 C2F5 F F
n-C5H11 C2F5 F F
n-C6H13 C2F5 F F
H C3F7 H H
CH3 C3F7 H H
C2H5 C3F7 H H
n-C3H7 C3F7 H H
n-C4H9 C3F7 H H
n-C5H11 C3F7 H H
n-C6H13 C3F7 H H
H C3F7 F H
CH3 C3F7 F H
C2H5 C3F7 F H
n-C3H7 C3F7 F H
n-C4H9 C3F7 F H
R1 X L1 L2
n-C5H11 C3F7 F H
n-C6H13 C3F7 F H
H C3F7 F F
CH3 C3F7 F F
C2H5 C3F7 F F
n-C3H7 C3F7 F F
n-C4H9 C3F7 F F
n-C5H11 C3F7 F F
n-C6H13 C3F7 F F
H SF5 H H
CH3 SF5 H H
C2H5 SF5 H H
n-C3H7 SF5 H H
n-C4H9 SF5 H H
n-C5H11 SF5 H H
n-C6H13 SF5 H H
H SF5 F H
CH3 SF5 F H
C2H5 SF5 F H
n-C3H7 SF5 F H
n-C4H9 SF5 F H
n-C5H11 SF5 F H
n-C6H13 SF5 F H
H SF5 F F
CH3 SF5 F F
C2H5 SF5 F F
n-C3H7 SF5 F F
n-C4H9 SF5 F F
n-C5H11 SF5 F F
n-C6H13 SF5 F F
H CN H H
CH3 CN H H
C2H5 CN H H
n-C3H7 CN H H
n-C4H9 CN H H
R1 X L1 L2
n-C5H11 CN H H
n-C6H13 CN H H
H CN F H
CH3 CN F H
C2H5 CN F H
n-C3H7 CN F H
n-C4H9 CN F H
n-C5H11 CN F H
n-C6H13 CN F H
H CN F F
CH3 CN F F
C2H5 CN F F
n-C3H7 CN F F
n-C4H9 CN F F
n-C5H11 CN F F
n-C6H13 CN F F
实施例2
步骤2.1
50mmol的I、50mmol的J、2.5mmol的Pd(PPh3)4、300ml的甲苯和300ml的硼酸钠缓冲液(pH=9)的混合物在80℃下搅拌18小时。将混合物倾倒在500ml的0.1N HCl中,产物用CH2Cl2萃取,Na2SO4干燥和在旋转蒸发器上蒸发至干。粗产物经色谱纯化(硅胶/庚烷),随后两次在-20℃下从正庚烷中重结晶。C 78 N 93.1l;Δn=0.1493;Δε=27.3。
类似地制备以下结构式的化合物:
R1 X L1 L2 L3 L4
H F H H H H
CH3 F H H H H
C2H5 F H H H H
C3H7 F H H H H
n-C4H9 F H H H H
n-C5H11 F H H H H
n-C6H13 F H H H H
H F F H H H
CH3 F F H H H
C2H5 F F H H H
n-C3H7 F F H H H
n-C4H9 F F H H H
n-C5H11 F F H H H
n-C6H13 F F H H H
H F F F H H
CH3 F F F H H
R1 X L1 L2 L3 L4
n-C3H7 F F F H H C 75 N 118.0 I;
Δε=23.2;Δn=0.1450
n-C4H9F F F H H
n-C5H11 F F F H H
n-C6H13 F F F H H
H Cl H H H H
CH3 Cl H H H H
C2H5 Cl H H H H
n-C3H7 Cl H H H H
n-C4H9 Cl H H H H
n-C5H11 Cl H H H H
n-C6H13 Cl H H H H
H Cl F H H H
CH3 Cl F H H H
C2H5 Cl F H H H
n-C3H7 Cl F H H H
n-C4H9 Cl F H H H
n-C5H11 Cl F H H H
n-C6H13 Cl F H H H
H Cl F F H H
CH3 Cl F F H H
C2H5 Cl F F H H
n-C3H7 Cl F F H H
n-C4H9 Cl F F H H
n-C5H11 Cl F F H H
n-C6H13 Cl F F H H
H OCF3 H H H H
CH3 OCF3 H H H H
C2H5 OCF3 H H H H
n-C3H7 OCF3 H H H H
n-C4H9 OCF3 H H H H
n-C5H11 OCF3 H H H H
n-C6H13 OCF3 H H H H
H OCF3 F H H H
CH3 OCF3 F H H H
R1 X L1 L2 L3 L4
C2H5 OCF3 F H H H
n-C3H7 OCF3 F H H H
n-C4H9 OCF3 F H H H
n-C5H11 OCF3 F H H H
n-C6H13 OCF3 F H H H
H OCF3 F F H H
CH3 OCF3 F F H H
C2H5 OCF3 F F H H
n-C3H7 OCF3 F F H H
n-C4H9 OCF3 F F H H
n-C5H11 OCF3 F F H H
n-C6H13 OCF3 F F H H
H OCHF2 H H H H
CH3 OCHF2 H H H H
C2H5 OCHF2 H H H H
n-C3H7 OCHF2 H H H H
n-C4H9 OCHF2 H H H H
n-C5H11 OCHF2 H H H H
n-C6H13 OCHF2 H H H H
H OCHF2 F H H H
CH3 OCHF2 F H H H
C2H5 OCHF2 F H H H
n-C3H7 OCHF2 F H H H
n-C4H9 OCHF2 F H H H
n-C5H11 OCHF2 F H H H
n-C6H13 OCHF2 F H H H
H OCHF2 F F H H
CH3 OCHF2 F F H H
C2H5 OCHF2 F F H H
n-C3H7 OCHF2 F F H H
n-C4H9 OCHF2 F F H H
n-C5H11 OCHF2 F F H H
n-C6H13 OCHF2 F F H H
H OCHFCF3 H H H H
CH3 OCHFCF3 H H H H
R1 X L1 L2 L3 L4
C2H5 OCHFCF3 H H H H
n-C3H7 OCHFCF3 H H H H
n-C4H9 OCHFCF3 H H H H
n-C5H11 OCHFCF3 H H H H
n-C6H13 OCHFCF3 H H H H
H OCHFCF3 F H H H
CH3 OCHFCF3 F H H H
C2H5 OCHFCF3 F H H H
n-C3H7 OCHFCF3 F H H H
n-C4H9 OCHFCF3 F H H H
n-C5H11 OCHFCF3 F H H H
n-C6H13 OCHFCF3 F H H H
H OCHFCF3 F F H H
CH3 OCHFCF3 F F H H
C2H5 OCHFCF3 F F H H
n-C3H7 OCHFCF3 F F H H
n-C4H9 OCHFCF3 F F H H
n-C5H11 OCHFCF3 F F H H
n-C6H13 OCHFCF3 F F H H
H OCHFCF3 H H H H
CH3 OCHFCF3 H H H H
C2H5 OCHFCF3 H H H H
n-C3H7 OCHFCF3 H H H H
n-C4H9 OCHFCF3 H H H H
n-C5H11 OCHFCF3 H H H H
n-C6H13 OCHFCF3 H H H H
H OCHFCF3 F H H H
CH3 OCHFCF3 F H H H
C2H5 OCHFCF3 F H H H
n-C3H7 OCHFCF3 F H H H
n-C4H9 OCHFCF3 F H H H
n-C5H11 OCHFCF3 F H H H
n-C6H13 OCHFCF3 F H H H
H OCHFCF3 F F H H
CH3 OCHFCF3 F F H H
R1 X L1 L2 L3 L4
C2H5 OCHFCF3 F F H H
n-C3H7 OCHFCF3 F F H H
n-C4H9 OCHFCF3 F F H H
n-C5H11 OCHFCF3 F F H H
n-C6H13 OCHFCF3 F F H H
H OCF2CHFCF3 H H H H
CH3 OCF2CHFCF3 H H H H
C2H5 OCF2CHFCF3 H H H H
n-C3H7 OCF2CHFCF3 H H H H
n-C4H9 OCF2CHFCF3 H H H H
n-C5H11 OCF2CHFCF3 H H H H
n-C6H13 OCF2CHFCF3 H H H H
H OCF2CHFCF3 F H H H
CH3 OCF2CHFCF3 F H H H
C2H5 OCF2CHFCF3 F H H H
n-C3H7 OCF2CHFCF3 F H H H
n-C4H9 OCF2CHFCF3 F H H H
n-C5H11 OCF2CHFCF3 F H H H
n-C6H13 OCF2CHFCF3 F H H H
H OCF2CHFCF3 F F H H
CH3 OCF2CHFCF3 F F H H
C2H5 OCF2CHFCF3 F F H H
n-C3H7 OCF2CHFCF3 F F H H
n-C4H9 OCF2CHFCF3 F F H H
n-C5H11 OCF2CHFCF3 F F H H
n-C6H13 OCF2CHFCF3 F F H H
H NCS H H H H
CH3 NCS H H H H
C2H5 NCS H H H H
n-C3H7 NCS H H H H
n-C4H9 NCS H H H H
n-C5H11 NCS H H H H
n-C6H13 NCS H H H H
H NCS F H H H
CH3 NCS F H H H
R1 X L1 L2 L3 L4
C2H5 NCS F H H H
n-C3H7 NCS F H H H
n-C4H9 NCS F H H H
n-C5H11 NCS F H H H
n-C6H13 NCS F H H H
H NCS F F H H
CH3 NCS F F H H
C2H5 NCS F F H H
n-C3H7 NCS F F H H
n-C4H9 NCS F F H H
n-C5H11 NCS F F H H
n-C6H13 NCS F F H H
H C2F5 H H H H
CH3 C2F5 H H H H
C2H5 C2F5 H H H H
n-C3H7 C2F5 H H H H
n-C4H9 C2F5 H H H H
n-C5H11 C2F5 H H H H
n-C6H13 C2F5 H H H H
H C2F5 F H H H
CH3 C2F5 F H H H
C2H5 C2F5 F H H H
n-C3H7 C2F5 F H H H
n-C4H9 C2F5 F H H H
n-C5H11 C2F5 F H H H
n-C6H13 C2F5 F H H H
H C2F5 F F H H
CH3 C2F5 F F H H
C2H5 C2F5 F F H H
n-C3H7 C2F5 F F H H
n-C4H9 C2F5 F F H H
n-C5H11 C2F5 F F H H
n-C6H13 C2F5 F F H H
H C3F7 H H H H
CH3 C3F7 H H H H
R1 X L1 L2 L3 L4
C2H5 C3F7 H H H H
n-C3H7 C3F7 H H H H
n-C4H9 C3F7 H H H H
n-C5H11 C3F7 H H H H
n-C6H13 C3F7 H H H H
H C3F7 F H H H
CH3 C3F7 F H H H
C2H5 C3F7 F H H H
n-C3H7 C3F7 F H H H
n-C4H9 C3F7 F H H H
n-C5H11 C3F7 F H H H
n-C6H13 C3F7 F H H H
H C3F7 F F H H
CH3 C3F7 F F H H
C2H5 C3F7 F F H H
n-C3H7 C3F7 F F H H
n-C4H9 C3F7 F F H H
n-C5H11 C3F7 F F H H
n-C6H13 C3F7 F F H H
H SF5 H H H H
CH3 SF5 H H H H
C2H5 SF5 H H H H
n-C3H7 SF5 H H H H
n-C4H9 SF5 H H H H
n-C5H11 SF5 H H H H
n-C6H13 SF5 H H H H
H SF5 F H H H
CH3 SF5 F H H H
C2H5 SF5 F H H H
n-C3H7 SF5 F H H H
n-C4H9 SF5 F H H H
n-C5H11 SF5 F H H H
n-C6H13 SF5 F H H H
H SF5 F F H H
CH3 SF5 F F H H
R1 X L1 L2 L3 L4
C2H5 SF5 F F H H
n-C3H7 SF5 F F H H
n-C4H9 SF5 F F H H
n-C5H11 SF5 F F H H
n-C6H13 SF5 F F H H
H CN H H H H
CH3 CN H H H H
C2H5 CN H H H H
n-C3H7 CN H H H H
n-C4H9 CN H H H H
n-C5H11 CN H H H H
n-C6H13 CN H H H H
H CN F H H H
CH3 CN F H H H
C2H5 CN F H H H
n-C3H7 CN F H H H
n-C4H9 CN F H H H
n-C5H11 CN F H H H
n-C6H13 CN F H H H
H CN F F H H
CH3 CN F F H H
C2H5 CN F F H H
n-C3H7 CN F F H H
n-C4H9 CN F F H H
n-C5H11 CN F F H H
n-C6H13 CN F F H H
H F H H F H
CH3 F H H F H
C2H5 F H H F H
C3H7 F H H F H
n-C4H9 F H H F H
n-C5H11 F H H F H
n-C6H13 F H H F H
H F F H F H
CH3 F F H F H
R1 X L1 L2 L3 L4
C2H5 F F H F H
n-C3H7 F F H F H
n-C4H9 F F H F H
n-C5H11 F F H F H
n-C6H13 F F H F H
H F F F F H
CH3 F F F F H
C2H5 F F F F H C 89 N(76.8) I;
Δε=29.9;Δn=0.1310
n-C3H7 F F F F H C 70 N 102.3 I;
Δε=29.7;Δn=0.1364
n-C4H9 F F F F H
n-C5H11 F F F F H
n-C6H13 F F F F H
H Cl H H F H
CH3 Cl H H F H
C2H5 Cl H H F H
n-C3H7 Cl H H F H
n-C4H9 Cl H H F H
n-C5H11 Cl H H F H
n-C6H13 Cl H H F H
H Cl F H F H
CH3 Cl F H F H
C2H5 Cl F H F H
n-C3H7 Cl F H F H
n-C4H9 Cl F H F H
n-C5H11 Cl F H F H
n-C6H13 Cl F H F H
H Cl F F F H
CH3 Cl F F F H
C2H5 Cl F F F H
n-C3H7 Cl F F F H
n-C4H9 Cl F F F H
n-C5H11 Cl F F F H
n-C6H13 Cl F F F H
R1 X L1 L2 L3 L4
H OCF3 H H F H
CH3 OCF3 H H F H
C2H5 OCF3 H H F H
n-C3H7 OCF3 H H F H
n-C4H9 OCF3 H H F H
n-C5H11 OCF3 H H F H
n-C6H13 OCF3 H H F H
H OCF3 F H F H
CH3 OCF3 F H F H
C2H5 OCF3 F H F H
n-C3H7 OCF3 F H F H
n-C4H9 OCF3 F H F H
n-C5H11 OCF3 F H F H
n-C6H13 OCF3 F H F H
H OCF3 F F F H
CH3 OCF3 F F F H
C2H5 OCF3 F F F H
n-C3H7 OCF3 F F F H
n-C4H9 OCF3 F F F H
n-C5H11 OCF3 F F F H
n-C6H13 OCF3 F F F H
H OCHF2 H H F H
CH3 OCHF2 H H F H
C2H5 OCHF2 H H F H
n-C3H7 OCHF2 H H F H
n-C4H9 OCHF2 H H F H
n-C5H11 OCHF2 H H F H
n-C6H13 OCHF2 H H F H
H OCHF2 F H F H
CH3 OCHF2 F H F H
C2H5 OCHF2 F H F H
n-C3H7 OCHF2 F H F H
n-C4H9 OCHF2 F H F H
n-C5H11 OCHF2 F H F H
n-C6H13 OCHF2 F H F H
R1 X L1 L2 L3 L4
H OCHF2 F F F H
CH3 OCHF2 F F F H
C2H5 OCHF2 F F F H
n-C3H7 OCHF2 F F F H
n-C4H9 OCHF2 F F F H
n-C5H11 OCHF2 F F F H
n-C6H13 OCHF2 F F F H
H OCHFCF3 H H F H
CH3 OCHFCF3 H H F H
C2H5 OCHFCF3 H H F H
n-C3H7 OCHFCF3 H H F H
n-C4H9 OCHFCF3 H H F H
n-C5H11 OCHFCF3 H H F H
n-C6H13 OCHFCF3 H H F H
H OCHFCF3 F H F H
CH3 OCHFCF3 F H F H
C2H5 OCHFCF3 F H F H
n-C3H7 OCHFCF3 F H F H
n-C4H9 OCHFCF3 F H F H
n-C5H11 OCHFCF3 F H F H
n-C6H13 OCHFCF3 F H F H
H OCHFCF3 F F F H
CH3 OCHFCF3 F F F H
C2H5 OCHFCF3 F F F H
n-C3H7 OCHFCF3 F F F H
n-C4H9 OCHFCF3 F F F H
n-C5H11 OCHFCF3 F F F H
n-C6H13 OCHFCF3 F F F H
H OCHFCF3 H H F H
CH3 OCHFCF3 H H F H
C2H5 OCHFCF3 H H F H
n-C3H7 OCHFCF3 H H F H
n-C4H9 OCHFCF3 H H F H
n-C5H11 OCHFCF3 H H F H
n-C6H13 OCHFCF3 H H F H
R1 X L1 L2 L3 L4
H OCHFCF3 F H F H
CH3 OCHFCF3 F H F H
C2H5 OCHFCF3 F H F H
n-C3H7 OCHFCF3 F H F H
n-C4H9 OCHFCF3 F H F H
n-C5H11 OCHFCF3 F H F H
n-C6H13 OCHFCF3 F H F H
H OCHFCF3 F F F H
CH3 OCHFCF3 F F F H
C2H5 OCHFCF3 F F F H
n-C3H7 OCHFCF3 F F F H
n-C4H9 OCHFCF3 F F F H
n-C5H11 OCHFCF3 F F F H
n-C6H13 OCHFCF3 F F F H
H OCF2CHFCF3 H H F H
CH3 OCF2CHFCF3 H H F H
C2H5 OCF2CHFCF3 H H F H
n-C3H7 OCF2CHFCF3 H H F H
n-C4H9 OCF2CHFCF3 H H F H
n-C5H11 OCF2CHFCF3 H H F H
n-C6H13 OCF2CHFCF3 H H F H
H OCF2CHFCF3 F H F H
CH3 OCF2CHFCF3 F H F H
C2H5 OCF2CHFCF3 F H F H
n-C3H7 OCF2CHFCF3 F H F H
n-C4H9 OCF2CHFCF3 F H F H
n-C5H11 OCF2CHFCF3 F H F H
n-C6H13 OCF2CHFCF3 F H F H
H OCF2CHFCF3 F F F H
CH3 OCF2CHFCF3 F F F H
C2H5 OCF2CHFCF3 F F F H
n-C3H7 OCF2CHFCF3 F F F H
n-C4H9 OCF2CHFCF3 F F F H
n-C5H11 OCF2CHFCF3 F F F H
n-C6H13 OCF2CHFCF3 F F F H
R1 X L1 L2 L3 L4
H NCS H H F H
CH3 NCS H H F H
C2H5 NCS H H F H
n-C3H7 NCS H H F H
n-C4H9 NCS H H F H
n-C5H11 NCS H H F H
n-C6H13 NCS H H F H
H NCS F H F H
CH3 NCS F H F H
C2H5 NCS F H F H
n-C3H7 NCS F H F H
n-C4H9 NCS F H F H
n-C5H11 NCS F H F H
n-C6H13 NCS F H F H
H NCS F F F H
CH3 NCS F F F H
C2H5 NCS F F F H
n-C3H7 NCS F F F H
n-C4H9 NCS F F F H
n-C5H11 NCS F F F H
n-C6H13 NCS F F F H
H C2F5 H H F H
CH3 C2F5 H H F H
C2H5 C2F5 H H F H
n-C3H7 C2F5 H H F H
n-C4H9 C2F5 H H F H
n-C5H11 C2F5 H H F H
n-C6H13 C2F5 H H F H
H C2F5 F H F H
CH3 C2F5 F H F H
C2H5 C2F5 F H F H
n-C3H7 C2F5 F H F H
n-C4H9 C2F5 F H F H
n-C5H11 C2F5 F H F H
n-C6H13 C2F5 F H F H
R1 X L1 L2 L3 L4
H C2F5 F F F H
CH3 C2F5 F F F H
C2H5 C2F5 F F F H
n-C3H7 C2F5 F F F H
n-C4H9 C2F5 F F F H
n-C5H11 C2F5 F F F H
n-C6H13 C2F5 F F F H
H C3F7 H H F H
CH3 C3F7 H H F H
C2H5 C3F7 H H F H
n-C3H7 C3F7 H H F H
n-C4H9 C3F7 H H F H
n-C5H11 C3F7 H H F H
n-C6H13 C3F7 H H F H
H C3F7 F H F H
CH3 C3F7 F H F H
C2H5 C3F7 F H F H
n-C3H7 C3F7 F H F H
n-C4H9 C3F7 F H F H
n-C5H11 C3F7 F H F H
n-C6H13 C3F7 F H F H
H C3F7 F F F H
CH3 C3F7 F F F H
C2H5 C3F7 F F F H
n-C3H7 C3F7 F F F H
n-C4H9 C3F7 F F F H
n-C5H11 C3F7 F F F H
n-C6H13 C3H7 F F F H
H SF5 H H F H
CH3 SF5 H H F H
C2H5 SF5 H H F H
n-C3H7 SF5 H H F H
n-C4H9 SF5 H H F H
n-C5H11 SF5 H H F H
n-C6H13 SF5 H H F H
R1 X L1 L2 L3 L4
H SF5 F H F H
CH3 SF5 F H F H
C2H5 SF5 F H F H
n-C3H7 SF5 F H F H
n-C4H9 SF5 F H F H
n-C5H11 SF5 F H F H
n-C6H13 SF5 F H F H
H SF5 F F F H
CH3 SF5 F F F H
C2H5 SF5 F F F H
n-C3H7 SF5 F F F H
n-C4H9 SF5 F F F H
n-C5H11 SF5 F F F H
n-C6H13 SF5 F F F H
H CN H H F H
CH3 CN H H F H
C2H5 CN H H F H
n-C3H7 CN H H F H
n-C4H9 CN H H F H
n-C5H11 CN H H F H
n-C6H13 CN H H F H
H CN F H F H
CH3 CN F H F H
C2H5 CN F H F H
n-C3H7 CN F H F H
n-C4H9 CN F H F H
n-C5H11 CN F H F H
n-C6H13 CN F H F H
H CN F F F H
CH3 CN F F F H
C2H5 CN F F F H
n-C3H7 CN F F F H
n-C4H9 CN F F F H
n-C5H11 CN F F F H
n-C6H13 CN F F F H
R1 X L1 L2 L3 L4
H F H H F F
CH3 F H H F F
C2H5 F H H F F
n-C4H9 F H H F F
n-C5H11 F H H F F
n-C6H13 F H H F F
H F F H F F
CH3 F F H F F
C2H5 F F H F F
n-C3H7 F F H F F
n-C4H9 F F H F F
n-C5H11 F F H F F
n-C6H13 F F H F F
H F F F F F
CH3 F F F F F
C2H5 F F F F F
C2H5 F F F F F C 91 N(58.8) I;
Δε=35.0;Δn=0.1149
n-C3H7 F F F F F C 83 N(83.0) I;
Δε=34.9;Δn=0.1231
n-C4H9 F F F F F C 90 N 79.4 I;
Δε=32.4;Δn=0.1171
n-C5H11 F F F F F C 82 N 84.3 I;
Δε=31.9;Δn=0.1205
n-C6H13 F F F F F C 89 N(83.4) I;
Δε=30.6;Δn=0.1116
n-C7H15 F F F F F C 82 N 84.3 I;
Δε=30.3;Δn=0.1130
H Cl H H F F
CH3 Cl H H F F
C2H5 Cl H H F F
n-C3H7 Cl H H F F
n-C4H9 Cl H H F F
n-C5H11 Cl H H F F
n-C6H13 Cl H H F F
R1 X L1 L2 L3 L4
H Cl F H F F
CH3 Cl F H F F
C2H5 Cl F H F F
n-C3H7 Cl F H F F
n-C4H9 Cl F H F F
n-C5H11 Cl F H F F
n-C6H13 Cl F H F F
H Cl F F F F
CH3 Cl F F F F
C2H5 Cl F F F F
n-C3H7 Cl F F F F C 80 N 106.7 I;
Δε=31.5;Δn=0.1372
n-C4H9 Cl F F F F
n-C5H11 Cl F F F F
n-C6H13 Cl F F F F
H OCF3 H H F F
CH3 OCF3 H H F F
C2H5 OCF3 H H F F
n-C3H7 OCF3 H H F F C 80 N 119.8 I;
Δε=25.3;Δn=0.1330
n-C4H9 OCF3 H H F F
n-C5H11 OCF3 H H F F
n-C6H13 OCF3H H F F
H OCF3 F H F F
CH3 OCF3 F H F F
C2H5 OCF3 F H F F
n-C3H7 OCF3 F H F F C 48 SA(46) N 105.1 I;
Δε=29.8;Δn=0.1180
n-C4H9 OCF3 F H F F
n-C5H11 OCF3 F H F F
n-C6H13 OCF3 F H F F
H OCF3 F F F F
CH3 OCF3 F F F F
C2H5 OCF3 F F F F
R1 X L1 L2 L3 L4
n-C3H7 OCF3 F F F F C 73 N 97.5 I;
Δε=35.6;Δn=0.1158
n-C4H9 OCF3 F F F F
n-C5H11 OCF3 F F F F
n-C6H13 OCF3 F F F F
H OCHF2 H H F F
CH3 OCHF2 H H F F
C2H5 OCHF2 H H F F
n-C3H7 OCHF2 H H F F
n-C4H9 OCHF2 H H F F
n-C5H11 OCHF2 H H F F
n-C6H13 OCHF2 H H F F
H OCHF2 F H F F
CH3 OCHF2 F H F F
C2H5 OCHF2 F H F F
n-C3H7 OCHF2 F H F F
n-C4H9 OCHF2 F H F F
n-C5H11 OCHF2 F H F F
n-C6H13 OCHF2 F H F F
H OCHF2 F F F F
CH3 OCHF2 F F F F
C2H5 OCHF2 F F F F
n-C3H7 OCHF2 F F F F
n-C4H9 OCHF2 F F F F
n-C5H11 OCHF2 F F F F
n-C6H13 OCHF2 F F F F
H OCHFCF3 H H F F
CH3 OCHFCF3 H H F F
C2H5 OCHFCF3 H H F F
n-C3H7 OCHFCF3 H H F F
n-C4H9 OCHFCF3 H H F F
n-C5H11 OCHFCF3 H H F F
n-C6H13 OCHFCF3 H H F F
H OCHFCF3 F H F F
CH3 OCHFCF3 F H F F
R1 X L1 L2 L3 L4
C2H5 OCHFCF3 F H F F
n-C3H7 OCHFCF3 F H F F
n-C4H9 OCHFCF3 F H F F
n-C5H11 OCHFCF3 F H F F
n-C6H13 OCHFCF3 F H F F
H OCHFCF3 F F F F
CH3 OCHFCF3 F F F F
C2H5 OCHFCF3 F F F F
n-C3H7 OCHFCF3 F F F F
n-C4H9 OCHFCF3 F F F F
n-C5H11 OCHFCF3 F F F F
n-C6H13 OCHFCF3 F F F F
H OCHFCF3 H H F F
CH3 OCHFCF3 H H F F
C2H5 OCHFCF3 H H F F
n-C3H7 OCHFCF3 H H F F
n-C4H9 OCHFCF3 H H F F
n-C5H11 OCHFCF3 H H F F
n-C6H13 OCHFCF3 H H F F
H OCHFCF3 F H F F
CH3 OCHFCF3 F H F F
C2H5 OCHFCF3 F H F F
n-C3H7 OCHFCF3 F H F F
n-C4H9 OCHFCF3 F H F F
n-C5H11 OCHFCF3 F H F F
n-C6H13 OCHFCF3 F H F F
H OCHFCF3 F F F F
CH3 OCHFCF3 F F F F
C2H5 OCHFCF3 F F F F
n-C3H7 OCHFCF3 F F F F
n-C4H9 OCHFCF3 F F F F
n-C5H11 OCHFCF3 F F F F
n-C6H13 OCHFCF3 F F F F
H OCF2CHFCF3 H H F F
CH3 OCF2CHFCF3 H H F F
R1 X L1 L2 L3 L4
C2H5 OCF2CHFCF3 H H F F
n-C3H7 OCF2CHFCF3 H H F F
n-C4H9 OCF2CHFCF3 H H F F
n-C5H11 OCF2CHFCF3 H H F F
n-C6H13 OCF2CHFCF3 H H F F
H OCF2CHFCF3 F H F F
CH3 OCF2CHFCF3 F H F F
C2H5 OCF2CHFCF3 F H F F
n-C3H7 OCF2CHFCF3 F H F F
n-C4H9 OCF2CHFCF3 F H F F
n-C5H11 OCF2CHFCF3 F H F F
n-C6H13 OCF2CHFCF3 F H F F
H OCF2CHFCF3 F F F F
CH3 OCF2CHFCF3 F F F F
C2H5 OCF2CHFCF3 F F F F
n-C3H7 OCF2CHFCF3 F F F F
n-C4H9 OCF2CHFCF3 F F F F
n-C5H11 OCF2CHFCF3 F F F F
n-C6H13 OCF2CHFCF3 F F F F
H NCS H H F F
CH3 NCS H H F F
C2H5 NCS H H F F
n-C3H7 NCS H H F F C 107 N 185.5 I;
Δε=31.4;Δn=0.2052
n-C4H9 NCS H H F F
n-C5H11 NCS H H F F
n-C6H13 NCS H H F F
H NCS F H F F
CH3 NCS F H F F
C2H5 NCS F H F F
n-C3H7 NCS F H F F
n-C4H9 NCS F H F F
n-C5H11 NCS F H F F
n-C6H13 NCS F H F F
H NCS F F F F
R1 X L1 L2 L3 L4
CH3 NCS F F F F
C2H5 NCS F F F F
n-C3H7 NCS F F F F
n-C4H9 NCS F F F F
n-C5H11 NCS F F F F
n-C6H13 NCS F F F F
H C2F5 H H F F
CH3 C2F5 H H F F
C2H5 C2F5 H H F F
n-C3H7 C2F5 H H F F
n-C4H9 C2F5 H H F F
n-C5H11 C2F5 H H F F
n-C6H13 C2F5 H H F F
H C2F5 F H F F
CH3 C2F5 F H F F
C2H5 C2F5 F H F F
n-C3H7 C2F5 F H F F
n-C4H9 C2F5 F H F F
n-C5H11 C2F5 F H F F
n-C6H13 C2F5 F H F F
H C2F5 F F F F
CH3 C2F5 F F F F
C2H5 C2F5 F F F F
n-C3H7 C2F5 F F F F
n-C4H9 C2F5 F F F F
n-C5H11 C2F5 F F F F
n-C6H13 C2F5 F F F F
H C3F7 H H F F
CH3 C3F7 H H F F
C2H5 C3F7 H H F F
n-C3H7 C3F7 H H F F
n-C4H9 C3F7 H H F F
n-C5H11 C3F7 H H F F
n-C6H13 C3F7 H H F F
H C3F7 F H F F
R1 X L1 L2 L3 L4
CH3 C3F7 F H F F
C2H5 C3F7 F H F F
n-C3H7 C3F7 F H F F
n-C4H9 C3F7 F H F F
n-C5H11 C3F7 F H F F
n-C6H13 C3F7 F H F F
H C3F7 F F F F
CH3 C3F7 F F F F
C2H5 C3F7 F F F F
n-C3H7 C3F7 F F F F
n-C4H9 C3F7 F F F F
n-C5H11 C3F7 F F F F
n-C6H13 C3F7 F F F F
H SF5 H H F F
CH3 SF5 H H F F
C2H5 SF5 H H F F
n-C3H7 SF5 H H F F
n-C4H9 SF5 H H F F
n-C5H11 SF5 H H F F
n-C6H13 SF5 H H F F
H SF5 F H F F
CH3 SF5 F H F F
C2H5 SF5 F H F F
n-C3H7 SF5 F H F F
n-C4H9 SF5 F H F F
n-C5H11 SF5 F H F F
n-C6H13 SF5 F H F F
H SF5 F F F F
CH3 SF5 F F F F
C2H5 SF5 F F F F
n-C3H7 SF5 F F F F C 110 N(83.4) I;
Δε=33.8;Δn=0.1211
n-C4H9 SF5 F F F F
n-C5H11 SF5 F F F F
n-C6H13 SF5 F F F F
R1 X L1 L2 L3 L4
H CN H H F F
CH3 CN H H F F
C2H5 CN H H F F
n-C3H7 CN H H F F
n-C4H9 CN H H F F
n-C5H11 CN H H F F
n-C6H13 CN H H F F
H CN F H F F
CH3 CN F H F F
C2H5 CN F H F F
n-C3H7 CN F H F F
n-C4H9 CN F H F F
n-C5H11 CN F H F F
n-C6H13 CN F H F F
H CN F F F F
CH3 CN F F F F
C2H5 CN F F F F C 98 NRe(71)SC(84)
N 127.6I
Δε=67.8;Δn=0.1459
n-C3H7 CN F F F F C 75Sc?(65) N 144.1 I
Δn=0.1561;Δε=66.5
n-C4H9 CN F F F F C 79 N 139.3 I;
Δε=64.2;Δn=0.1477
n-C5H11 CN F F F F C 65 SC(44)N 141.5 I;
Δε=61.8;Δn=0.1490
n-C6H13 CN F F F F
n-C7H15 CN F F F F C 51 N 130.8 I;
Δε=58.4;Δn=0.1459
H CF3 H H F F
C2H5 CF3 H H F F
n-C3H7 CF3 H H F F C 95 N(87.5) I;
Δε=31.5;Δn=0.1330
n-C4H9 CF3 H H F F
n-C5H11 CF3 H H F F
n-C6H13 CF3 H H F F
R1 X L1 L2 L3 L4
CH2=CH CF3 H H F F
H CF3 F F F F
C2H5 CF3 F F F F
n-C3H7 CF3 F F F F C 91 I;
Δn=0.1190;Δε=40.8
n-C4H9 CF3 F F F F
n-C5H11 CF3 F F F F
n-C6H13 CF3 F F F F
CH2=CH CF3 F F F F
H F H H F F
C2H5 F H H F F
n-C3H7 F H H F F
n-C4H9 F H H F F
n-C5H11 F H H F F
n-C6H13 F H H F F
CH2=CH F H H F F
实施例3
步骤3.1
62.7mmol的三氟甲磺酸在-20℃下滴加到61.2mmol的L在500ml的CH2Cl2中的溶液中。混合物经30分钟升至室温,然后冷却至-70℃。首先添加91mmol的4-溴-3-氟苯酚和101mmol三乙基胺在200mlCH2Cl2中的溶液,5分钟过后添加310mmol的三乙基胺三(氢氟酸盐)。在另外5分钟之后,以多个小份添加315mmol的1,3-二溴-5,5-二甲基乙内酰脲的悬浮液,然后混合物在-70℃下搅拌另外1小时。反应混合物升至-10℃和然后倾倒在冰冷Na OH中。混合物进行常规水后处理,粗产物通过硅胶色谱分离(庚烷/MTB醚4∶1)和在-20℃下从乙醇中重结晶来提纯。
步骤3.2
50mmol的M、50mmol的3,4,5-三氟苯硼酸、2.5mmol的Pd(PPh3)4、300ml的甲苯和300ml的硼酸钠缓冲液(pH=9)的混合物在80℃下搅拌18小时。将混合物倾倒在500ml的0.1N HCl中,产物用CH2Cl2萃取,Na2SO4干燥和在旋转蒸发器上蒸发至干。粗产物色谱纯化(硅胶/正庚烷),随后在-20℃下从正庚烷中重结晶。C 61 N 191.8 l;Δn=0.1220;Δε=19.1。
类似地制备以下结构式的化合物:
R1 X L1 L2
H F H H
CH3 F H H
C2H5 F H H
n-C3H7 F H H C 84 N 232.4 I;
Δε=9.4;Δn=0.1390
n-C4H9 F H H
n-C5H11 F H H
n-C6H13 F H H
H F F H
CH3 F F H
C2H5 F F H
n-C3H7 F F H C 44 SM?45 N 212.6 I;
Δε=13.4;Δn=0.1328
n-C4H9 F F H
n-C5H11 F F H
n-C6H13 F F H
H F F F
CH3 F F F
C2H5 F F F
n-C4H9 F F F
n-C5H11 F F F
n-C6H13 F F F
H Cl H H
CH3 Cl H H
C2H5 Cl H H
n-C3H7 Cl H H
n-C4H9 Cl H H
n-C5H11 Cl H H
n-C6H13 Cl H H
H Cl F H
CH3 Cl F H
C2H5 Cl F H
n-C3H7 Cl F H
R1 X L1 L2
n-C4H9 Cl F H
n-C5H11 Cl F H
n-C6H13 Cl F H
H Cl F F
CH3 Cl F F
C2H5 Cl F F
n-C3H7 Cl F F
n-C4H9 Cl F F
n-C5H11 Cl F F
n-C6H13 Cl F F
H OCF3 H H
CH3 OCF3 H H
C2H5 OCF3 H H
n-C3H7 OCF3 H H
n-C4H9 OCF3 H H
n-C5H11 OCF3 H H
n-C6H13 OCF3 H H
H OCF3 F H
CH3 OCF3 F H
C2H5 OCF3 F H
n-C3H7 OCF3 F H
n-C4H9 OCF3 F H
n-C5H11 OCF3 F H
n-C6H13 OCF3 F H
H OCF3 F F
CH3 OCF3 F F
C2H5 OCF3 F F
n-C3H7 OCF3 F F
n-C4H9 OCF3 F F
n-C5H11 OCF3 F F
n-C6H13 OCF3 F F
H OCHF2 H H
CH3 OCHF2 H H
C2H5 OCHF2 H H
n-C3H7 OCHF2 H H
R1 X L1 L2
n-C4H9 OCHF2 H H
n-C5H11 OCHF2 H H
n-C6H13 OCHF2 H H
H OCHF2 F H
CH3 OCHF2 F H
C2H5 OCHF2 F H
n-C3H7 OCHF2 F H
n-C4H9 OCHF2 F H
n-C5H11 OCHF2 F H
n-C6H13 OCHF2 F H
H OCHF2 F F
CH3 OCHF2 F F
C2H5 OCHF2 F F
n-C3H7 OCHF2 F F
n-C4H9 OCHF2 F F
n-C5H11 OCHF2 F F
n-C6H13 OCHF2 F F
H OCHFCF3 H H
CH3 OCHFCF3 H H
C2H5 OCHFCF3 H H
n-C3H7 OCHFCF3 H H
n-C4H9 OCHFCF3 H H
n-C5H11 OCHFCF3 H H
n-C6H13 OCHFCF3 H H
H OCHFCF3 F H
CH3 OCHFCF3 F H
C2H5 OCHFCF3 F H
n-C3H7 OCHFCF3 F H
n-C4H9 OCHFCF3 F H
n-C5H11 OCHFCF3 F H
n-C6H13 OCHFCF3 F H
H OCHFCF3 F F
CH3 OCHFCF3 F F
C2H5 OCHFCF3 F F
n-C3H7 OCHFCF3 F F
R1 X L1 L2
n-C4H9 OCHFCF3 F F
n-C5H11 OCHFCF3 F F
n-C6H13 OCHFCF3 F F
H OCHFCF3 H H
CH3 OCHFCF3 H H
C2H5 OCHFCF3 H H
n-C3H7 OCHFCF3 H H
n-C4H9 OCHFCF3 H H
n-C5H11 OCHFCF3 H H
n-C6H13 OCHFCF3 H H
H OCHFCF3 F H
CH3 OCHFCF3 F H
C2H5 OCHFCF3 F H
n-C3H7 OCHFCF3 F H
n-C4H9 OCHFCF3 F H
n-C5H11 OCHFCF3 F H
n-C6H13 OCHFCF3 F H
H OCHFCF3 F F
CH3 OCHFCF3 F F
C2H5 OCHFCF3 F F
n-C3H7 OCHFCF3 F F
n-C4H9 OCHFCF3 F F
n-C5H11 OCHFCF3 F F
n-C6H13 OCHFCF3 F F
H OCF2CHFCF3 H H
CH3 OCF2CHFCF3 H H
C2H5 OCF2CHFCF3 H H
n-C3H7 OCF2CHFCF3 H H
n-C4H9 OCF2CHFCF3 H H
n-C5H11 OCF2CHFCF3 H H
n-C6H13 OCF2CHFCF3 H H
H OCF2CHFCF3 F H
CH3 OCF2CHFCF3 F H
C2H5 OCF2CHFCF3 F H
n-C3H7 OCF2CHFCF3 F H
R1 X L1 L2
n-C4H9 OCF2CHFCF3 F H
n-C5H11 OCF2CHFCF3 F H
n-C6H13 OCF2CHFCF3 F H
H OCF2CHFCF3 F F
CH3 OCF2CHFCF3 F F
C2H5 OCF2CHFCF3 F F
n-C3H7 OCF2CHFCF3 F F
n-C4H9 OCF2CHFCF3 F F
n-C5H11 OCF2CHFCF3 F F
n-C6H13 OCF2CHFCF3 F F
H NCS H H
CH3 NCS H H
C2H5 NCS H H
n-C3H7 NCS H H
n-C4H9 NCS H H
n-C5H11 NCS H H
n-C6H13 NCS H H
H NCS F H
CH3 NCS F H
C2H5 NCS F H
n-C3H7 NCS F H
n-C4H9 NCS F H
n-C5H11 NCS F H
n-C6H13 NCS F H
H NCS F F
CH3 NCS F F
C2H5 NCS F F
n-C3H7 NCS F F
n-C4H9 NCS F F
n-C5H11 NCS F F
n-C6H13 NCS F F
H C2F5 H H
CH3 C2F5 H H
C2H5 C2F5 H H
n-C3H7 C2F5 H H
R1 X L1 L2
n-C4H9 C2F5 H H
n-C5H11 C2F5 H H
n-C6H13 C2F5 H H
H C2F5 F H
CH3 C2F5 F H
C2H5 C2F5 F H
n-C3H7 C2F5 F H
n-C4H9 C2F5 F H
n-C5H11 C2F5 F H
n-C6H13 C2F5 F H
H C2F5 F F
CH3 C2F5 F F
C2H5 C2F5 F F
n-C3H7 C2F5 F F
n-C4H9 C2F5 F F
n-C5H11 C2F5 F F
n-C6H13 C2F5 F F
H C3F7 H H
CH3 C3F7 H H
C2H5 C3F7 H H
n-C3H7 C3F7 H H
n-C4H9 C3F7 H H
n-C5H11 C3F7 H H
n-C6H13 C3F7 H H
H C3F7 F H
CH3 C3F7 F H
C2H5 C3F7 F H
n-C3H7 C3F7 F H
n-C4H9 C3F7 F H
n-C5H11 C3F7 F H
n-C6H13 C3F7 F H
H C3F7 F F
CH3 C3F7 F F
C2H5 C3F7 F F
n-C3H7 C3F7 F F
R1 X L1 L2
n-C4H9 C3F7 F F
n-C5H11 C3F7 F F
n-C6H13 C3F7 F F
H SF5 H H
CH3 SF5 H H
C2H5 SF5 H H
n-C3H7 SF5 H H
n-C4H9 SF5 H H
n-C5H11 SF5 H H
n-C6H13 SF5 H H
H SF5 F H
CH3 SF5 F H
C2H5 SF5 F H
n-C3H7 SF5 F H
n-C4H9 SF5 F H
n-C5H11 SF5 F H
n-C6H13 SF5 F H
H SF5 F F
CH3 SF5 F F
C2H5 SF5 F F
n-C3H7 SF5 F F
n-C4H9 SF5 F F
n-C5H11 SF5 F F
n-C6H13 SF5 F F
H CN H H
CH3 CN H H
C2H5 CN H H
n-C3H7 CN H H
n-C4H9 CN H H
n-C5H11 CN H H
n-C6H13 CN H H
H CN F H
CH3 CN F H
C2H5 CN F H
n-C3H7 CN F H
n-C4H9 CN F H
实施例4
步骤4.1
62.7mmol的三氟甲磺酸在-20℃下滴加到61.2mmol的N在500ml的CH2Cl2中的溶液中。混合物经30分钟升至室温,然后冷却至-70℃。然后,首先添加91mmol的4-溴苯酚和101mmol三乙基胺在200mlCH2Cl2中的溶液,5分钟过后添加310mmol的三乙基胺三(氢氟酸盐)。在另外5分钟之后,以多个小份添加315mmol的1,3-二溴-5,5-二甲基乙内酰脲的悬浮液,然后混合物在-70℃下搅拌另外1小时。反应混合物升至-10℃和然后倾倒在冰冷NaOH中。混合物进行常规水后处理,粗产物通过硅胶色谱分离(庚烷/MTB醚4∶1)和在-20℃下从乙醇中重结晶来提纯。
步骤4.2
50mmol的0、50mmol的3,4,5-三氟苯硼酸、2.5mmol的Pd(PPh3)4、300ml的甲苯和300ml的硼酸钠缓冲液(pH=9)的混合物在80℃下搅拌18小时。将混合物倾倒在500ml的0.1N HCl中,产物用CH2Cl2萃取,萃取物经Na2SO4干燥和在旋转蒸发器上蒸发至干。粗产物进行色谱分离(硅胶/正庚烷)和随后在-20℃下从正庚烷中重结晶。C 60 SB 81 N206.6l;Δn=0.1291;Δε=15.7。
类似地制备以下结构式的化合物:
R1 X L1 L2
H F H H
CH3 F H H
C2H5 F H H
n-C3H7 F H H
n-C4H9 F H H
n-C5H11 F H H
n-C6H13 F H H
H F F H
CH3 F F H
R1 X L1 L2
C2H5 F F H
n-C3H7 F F H C 47 SB 91N 238.0I;
Δε=10.7;Δn=0.1370
n-C4H9 F F H
n-C5H11 F F H
n-C6H13 F F H
H F F F
CH3 F F F
C2H5 F F F
n-C4H9 F F F
n-C5H11 F F F
n-C6H13 F F F
H Cl H H
CH3 Cl H H
C2H5 Cl H H
n-C3H7 Cl H H
n-C4H9 Cl H H
n-C5H11 Cl H H
n-C6H13 Cl H H
H Cl F H
CH3 Cl F H
C2H5 Cl F H
n-C3H7 Cl F H
n-C4H9 Cl F H
n-C5H11 Cl F H
n-C6H13 Cl F H
H Cl F F
CH3 Cl F F
C2H5 Cl F F
n-C3H7 Cl F F
n-C4H9 Cl F F
n-C5H11 Cl F F
n-C6H13 Cl F F
H OCF3 H H
CH3 OCF3 H H
R1 X L1 L2
C2H5 OCF3 H H
n-C3H7 OCF3 H H
n-C4H9 OCF3 H H
n-C5H11 OCF3 H H
n-C6H13 OCF3 H H
H OCF3 F H
CH3 OCF3 F H
C2H5 OCF3 F H
n-C3H7 OCF3 F H
n-C4H9 OCF3 F H
n-C5H11 OCF3 F H
n-C6H13 OCF3 F H
H OCF3 F F
CH3 OCF3 F F
C2H5 OCF3 F F
n-C3H7 OCF3 F F
n-C4H9 OCF3 F F
n-C5H11 OCF3 F F
n-C6H13 OCF3 F F
H OCHF2 H H
CH3 OCHF2 H H
C2H5 OCHF2 H H
n-C3H7 OCHF2 H H
n-C4H9 OCHF2 H H
n-C5H11 OCHF2 H H
n-C6H13 OCHF2 H H
H OCHF2 F H
CH3 OCHF2 F H
C2H5 OCHF2 F H
n-C3H7 OCHF2 F H
n-C4H9 OCHF2 F H
n-C5H11 OCHF2 F H
n-C6H13 OCHF2 F H
H OCHF2 F F
CH3 OCHF2 F F
R1 X L1 L2
C2H5 OCHF2 F F
n-C3H7 OCHF2 F F
n-C4H9 OCHF2 F F
n-C5H11 OCHF2 F F
n-C6H13 OCHF2 F F
H OCHFCF3 H H
CH3 OCHFCF3 H H
C2H5 OCHFCF3 H H
n-C3H7 OCHFCF3 H H
n-C4H9 OCHFCF3 H H
n-C5H11 OCHFCF3 H H
n-C6H13 OCHFCF3 H H
H OCHFCF3 F H
CH3 OCHFCF3 F H
C2H5 OCHFCF3 F H
n-C3H7 OCHFCF3 F H
n-C4H9 OCHFCF3 F H
n-C5H11 OCHFCF3 F H
n-C6H13 OCHFCF3 F H
H OCHFCF3 F F
CH3 OCHFCF3 F F
C2H5 OCHFCF3 F F
n-C3H7 OCHFCF3 F F
n-C4H9 OCHFCF3 F F
n-C5H11 OCHFCF3 F F
n-C6H13 OCHFCF3 F F
H OCHFCF3 H H
CH3 OCHFCF3 H H
C2H5 OCHFCF3 H H
n-C3H7 OCHFCF3 H H
n-C4H9 OCHFCF3 H H
n-C5H11 OCHFCF3 H H
n-C6H13 OCHFCF3 H H
H OCHFCF3 F H
CH3 OCHFCF3 F H
R1 X L1 L2
C2H5 OCHFCF3 F H
n-C3H7 OCHFCF3 F H
n-C4H9 OCHFCF3 F H
n-C5H11 OCHFCF3 F H
n-C6H13 OCHFCF3 F H
H OCHFCF3 F F
CH3 OCHFCF3 F F
C2H5 OCHFCF3 F F
n-C3H7 OCHFCF3 F F
n-C4H9 OCHFCF3 F F
n-C5H11 OCHFCF3 F F
n-C6H13 OCHFCF3 F F
H OCF2CHFCF3 H H
CH3 OCF2CHFCF3 H H
C2H5 OCF2CHFCF3 H H
n-C3H7 OCF2CHFCF3 H H
n-C4H9 OCF2CHFCF3 H H
n-C5H11 OCF2CHFCF3 H H
n-C6H13 OCF2CHFCF3 H H
H OCF2CHFCF3 F H
CH3 OCF2CHFCF3 F H
C2H5 OCF2CHFCF3 F H
n-C3H7 OCF2CHFCF3 F H
n-C4H9 OCF2CHFCF3 F H
n-C5H11 OCF2CHFCF3 F H
n-C6H13 OCF2CHFCF3 F H
H OCF2CHFCF3 F F
CH3 OCF2CHFCF3 F F
C2H5 OCF2CHFCF3 F F
n-C3H7 OCF2CHFCF3 F F
n-C4H9 OCF2CHFCF3 F F
n-C5H11 OCF2CHFCF3 F F
n-C6H13 OCF2CHFCF3 F F
H NCS H H
CH3 NCS H H
R1 X L1 L2
C2H5 NCS H H
n-C3H7 NCS H H
n-C4H9 NCS H H
n-C5H11 NCS H H
n-C6H13 NCS H H
H NCS F H
CH3 NCS F H
C2H5 NCS F H
n-C3H7 NCS F H
n-C4H9 NCS F H
n-C5H11 NCS F H
n-C6H13 NCS F H
H NCS F F
CH3 NCS F F
C2H5 NCS F F
n-C3H7 NCS F F
n-C4H9 NCS F F
n-C5H11 NCS F F
n-C6H13 NCS F F
H C2F5 H H
CH3 C2F5 H H
C2H5 C2F5 H H
n-C3H7 C2F5 H H
n-C4H9 C2F5 H H
n-C5H11 C2F5 H H
n-C6H13 C2F5 H H
H C2F5 F H
CH3 C2F5 F H
C2H5 C2F5 F H
n-C3H7 C2F5 F H
n-C4H9 C2F5 F H
n-C5H11 C2F5 F H
n-C6H13 C2F5 F H
H C2F5 F F
CH3 C2F5 F F
R1 X L1 L2
C2H5 C2F5 F F
n-C3H7 C2F5 F F
n-C4H9 C2F5 F F
n-C5H11 C2F5 F F
n-C6H13 C2F5 F F
H C3F7 H H
CH3 C3F7 H H
C2H5 C3F7 H H
n-C3H7 C3F7 H H
n-C4H9 C3F7 H H
n-C5H11 C3F7 H H
n-C6H13 C3F7 H H
H C3F7 F H
CH3 C3F7 F H
C2H5 C3F7 F H
n-C3H7 C3F7 F H
n-C4H9 C3F7 F H
n-C5H11 C3F7 F H
n-C6H13 C3F7 F H
H C3F7 F F
CH3 C3F7 F F
C2H5 C3F7 F F
n-C3H7 C3F7 F F
n-C4H9 C3F7 F F
n-C5H11 C3F7 F F
n-C6H13 C3F7 F F
H SF5 H H
CH3 SF5 H H
C2H5 SF5 H H
n-C3H7 SF5 H H
n-C4H9 SF5 H H
n-C5H11 SF5 H H
n-C6H13 SF5 H H
H SF5 F H
CH3 SF5 F H
R1 X L1 L2
C2H5 SF5 F H
n-C3H7 SF5 F H
n-C4H9 SF5 F H
n-C5H11 SF5 F H
n-C6H13 SF5 F H
H SF5 F F
CH3 SF5 F F
C2H5 SF5 F F
n-C3H7 SF5 F F
n-C4H9 SF5 F F
n-C5H11 SF5 F F
n-C6H13 SF5 F F
H CN H H
CH3 CN H H
C2H5 CN H H
n-C3H7 CN H H
n-C4H9 CN H H
n-C5H11 CN H H
n-C6H13 CN H H
实施例5
步骤5.1
98mmol的Q和16.3ml的三乙基胺(117mmol)在80ml二氯甲烷中的混合物在搅拌下滴加到65mmol的P在100ml二氯甲烷中的已冷却至-70℃的溶液中。当加料结束时,混合物在-70℃下搅拌另外1小时。随后在同一温度下滴加325mmol的三乙基胺三氢氟酸盐。随后在-70℃下滴加325mmo l的溴。在-70℃下搅拌1小时之后,反应混合物升至-10℃,倾倒在500ml的冰-水和95ml的32%氢氧化钠溶液的混合物中。分相,水相用二氯甲烷萃取。合并的有机相进行常规后处理。
步骤5.2
10mmol的S和10mmol的2,6-二氟-4-(反式-5′-丙基-四氢吡喃基-(2))-苯基硼酸在60ml甲苯和60ml的硼酸钠缓冲溶液(pH=9)中的混合物在0.5mmol的Pd(PPh3)4存在下,在80℃和搅拌下加热16小时。在冷却之后,将两相反应混合物在搅拌下倾倒在100ml的0.1N HCl中,分离出有机相,水相用甲苯萃取两次。干燥合并的甲苯相并进行蒸发,残留物经硅胶过滤(庚烷/甲基叔丁基醚)。最终,产物首先从乙醇中重结晶,然后从正庚烷中重结晶。C 115 N 197.7 l;Δε=35.4;Δn=0.1706。
类似地制备以下结构式的化合物:
R1 X L1 L2 L3 L4
H F H H H H
CH3 F H H H H
C2H5 F H H H H
C3H7 F H H H H
n-C4H9 F H H H H
n-C5H11 F H H H H
n-C6H13 F H H H H
R1 X L1 L2 L3 L4
H F F H H H
CH3 F F H H H
C2H5 F F H H H
n-C3H7 F F H H H
n-C4H9 F F H H H
n-C5H11 F F H H H
n-C6H13 F F H H H
H F F F H H
CH3 F F F H H
n-C4H9 F F F H H
n-C5H11 F F F H H
n-C6H13 F F F H H
H Cl H H H H
CH3 Cl H H H H
C2H5 Cl H H H H
n-C3H7 Cl H H H H
n-C4H9 Cl H H H H
n-C5H11 Cl H H H H
n-C6H13 Cl H H H H
H Cl F H H H
CH3 Cl F H H H
C2H5 Cl F H H H
n-C3H7 Cl F H H H
n-C4H9 Cl F H H H
n-C5H11 Cl F H H H
n-C6H13 Cl F H H H
H Cl F F H H
CH3 Cl F F H H
C2H5 Cl F F H H
n-C3H7 Cl F F H H
n-C4H9 Cl F F H H
n-C5H11 Cl F F H H
n-C6H13 Cl F F H H
H OCF3 H H H H
CH3 OCF3 H H H H
R1 X L1 L2 L3 L4
C2H5 OCF3 H H H H
n-C3H7 OCF3 H H H H
n-C4H9 OCF3 H H H H
n-C5H11 OCF3 H H H H
n-C6H13 OCF3 H H H H
H OCF3 F H H H
CH3 OCF3 F H H H
C2H5 OCF3 F H H H
n-C3H7 OCF3 F H H H
n-C4H9 OCF3 F H H H
n-C5H11 OCF3 F H H H
n-C6H13 OCF3 F H H H
H OCF3 F F H H
CH3 OCF3 F F H H
C2H5 OCF3 F F H H
n-C3H7 OCF3 F F H H
n-C4H9 OCF3 F F H H
n-C5H11 OCF3 F F H H
n-C6H13 OCF3 F F H H
H OCHF2 H H H H
CH3 OCHF2 H H H H
C2H5 OCHF2 H H H H
n-C3H7 OCHF2 H H H H
n-C4H9 OCHF2 H H H H
n-C5H11 OCHF2 H H H H
n-C6H13 OCHF2 H H H H
H OCHF2 F H H H
CH3 OCHF2 F H H H
C2H5 OCHF2 F H H H
n-C3H7 OCHF2 F H H H
n-C4H9 OCHF2 F H H H
n-C5H11 OCHF2 F H H H
n-C6H13 OCHF2 F H H H
H OCHF2 F F H H
CH3 OCHF2 F F H H
R1 X L1 L2 L3 L4
C2H5 OCHF2 F F H H
n-C3H7 OCHF2 F F H H
n-C4H9 OCHF2 F F H H
n-C5H11 OCHF2 F F H H
n-C6H13 OCHF2 F F H H
H OCHFCF3 H H H H
CH3 OCHFCF3 H H H H
C2H5 OCHFCF3 H H H H
n-C3H7 OCHFCF3 H H H H
n-C4H9 OCHFCF3 H H H H
n-C5H11 OCHFCF3 H H H H
n-C6H13 OCHFCF3 H H H H
H OCHFCF3 F H H H
CH3 OCHFCF3 F H H H
C2H5 OCHFCF3 F H H H
n-C3H7 OCHFCF3 F H H H
n-C4H9 OCHFCF3 F H H H
n-C5H11 OCHFCF3 F H H H
n-C6H13 OCHFCF3 F H H H
H OCHFCF3 F F H H
CH3 OCHFCF3 F F H H
C2H5 OCHFCF3 F F H H
n-C3H7 OCHFCF3 F F H H
n-C4H9 OCHFCF3 F F H H
n-C5H11 OCHFCF3 F F H H
n-C6H13 OCHFCF3 F F H H
H OCHFCF3 H H H H
CH3 OCHFCF3 H H H H
C2H5 OCHFCF3 H H H H
n-C3H7 OCHFCF3 H H H H
n-C4H9 OCHFCF3 H H H H
n-C5H11 OCHFCF3 H H H H
n-C6H13 OCHFCF3 H H H H
H OCHFCF3 F H H H
CH3 OCHFCF3 F H H H
R1 X L1 L2 L3 L4
C2H5 OCHFCF3 F H H H
n-C3H7 OCHFCF3 F H H H
n-C4H9 OCHFCF3 F H H H
n-C5H11 OCHFCF3 F H H H
n-C6H13 OCHFCF3 F H H H
H OCHFCF3 F F H H
CH3 OCHFCF3 F F H H
C2H5 OCHFCF3 F F H H
n-C3H7 OCHFCF3 F F H H
n-C4H9 OCHFCF3 F F H H
n-C5H11 OCHFCF3 F F H H
n-C6H13 OCHFCF3 F F H H
H OCF2CHFCF3 H H H H
CH3 OCF2CHFCF3 H H H H
C2H5 OCF2CHFCF3 H H H H
n-C3H7 OCF2CHFCF3 H H H H
n-C4H9 OCF2CHFCF3 H H H H
n-C5H11 OCF2CHFCF3 H H H H
n-C6H13 OCF2CHFCF3 H H H H
H OCF2CHFCF3 F H H H
CH3 OCF2CHFCF3 F H H H
C2H5 OCF2CHFCF3 F H H H
n-C3H7 OCF2CHFCF3 F H H H
n-C4H9 OCF2CHFCF3 F H H H
n-C5H11 OCF2CHFCF3 F H H H
n-C6H13 OCF2CHFCF3 F H H H
H OCF2CHFCF3 F F H H
CH3 OCF2CHFCF3 F F H H
C2H5 OCF2CHFCF3 F F H H
n-C3H7 OCF2CHFCF3 F F H H
n-C4H9 OCF2CHFCF3 F F H H
n-C5H11 OCF2CHFCF3 F F H H
n-C6H13 OCF2CHFCF3 F F H H
H NCS H H H H
CH3 NCS H H H H
R1 X L1 L2 L3 L4
C2H5 NCS H H H H
n-C3H7 NCS H H H H
n-C4H9 NCS H H H H
n-C5H11 NCS H H H H
n-C6H13 NCS H H H H
H NCS F H H H
CH3 NCS F H H H
C2H5 NCS F H H H
n-C3H7 NCS F H H H
n-C4H9 NCS F H H H
n-C5H11 NCS F H H H
n-C6H13 NCS F H H H
H NCS F F H H
CH3 NCS F F H H
C2H5 NCS F F H H
n-C3H7 NCS F F H H
n-C4H9 NCS F F H H
n-C5H11 NCS F F H H
n-C6H13 NCS F F H H
H C2F5 H H H H
CH3 C2F5 H H H H
C2H5 C2F5 H H H H
n-C3H7 C2F5 H H H H
n-C4H9 C2F5 H H H H
n-C5H11 C2F5 H H H H
n-C6H13 C2F5 H H H H
H C2F5 F H H H
CH3 C2F5 F H H H
C2H5 C2F5 F H H H
n-C3H7 C2F5 F H H H
n-C4H9 C2F5 F H H H
n-C5H11 C2F5 F H H H
n-C6H13 C2F5 F H H H
H C2F5 F F H H
CH3 C2F5 F F H H
R1 X L1 L2 L3 L4
C2H5 C2F5 F F H H
n-C3H7 C2F5 F F H H
n-C4H9 C2F5 F F H H
n-C5H11 C2F5 F F H H
n-C6H13 C2F5 F F H H
H C3F7 H H H H
CH3 C3F7 H H H H
C2H5 C3F7 H H H H
n-C3H7 C3F7 H H H H
n-C4H9 C3F7 H H H H
n-C5H11 C3F7 H H H H
n-C6H13 C3F7 H H H H
H C3F7 F H H H
CH3 C3F7 F H H H
C2H5 C3F7 F H H H
n-C3H7 C3F7 F H H H
n-C4H9 C3F7 F H H H
n-C5H11 C3F7 F H H H
n-C6H13 C3F7 F H H H
H C3F7 F F H H
CH3 C3F7 F F H H
C2H5 C3F7 F F H H
n-C3H7 C3F7 F F H H
n-C4H9 C3F7 F F H H
n-C5H11 C3F7 F F H H
n-C6H13 C3F7 F F H H
H SF5 H H H H
CH3 SF5 H H H H
C2H5 SF5 H H H H
n-C3H7 SF5 H H H H
n-C4H9 SF5 H H H H
n-C5H11 SF5 H H H H
n-C6H13 SF5 H H H H
H SF5 F H H H
CH3 SF5 F H H H
R1 X L1 L2 L3 L4
C2H5 SF5 F H H H
n-C3H7 SF5 F H H H
n-C4H9 SF5 F H H H
n-C5H11 SF5 F H H H
n-C6H13 SF5 F H H H
H SF5 F F H H
CH3 SF5 F F H H
C2H5 SF5 F F H H
n-C3H7 SF5 F F H H
n-C4H9 SF5 F F H H
n-C5H11 SF5 F F H H
n-C6H13 SF5 F F H H
H CN H H H H
CH3 CN H H H H
C2H5 CN H H H H
n-C3H7 CN H H H H
n-C4H9 CN H H H H
n-C5H11 CN H H H H
n-C6H13 CN H H H H
H CN F H H H
CH3 CN F H H H
C2H5 CN F H H H
n-C3H7 CN F H H H
n-C4H9 CN F H H H
n-C5H11 CN F H H H
n-C6H13 CN F H H H
H CN F F H H
CH3 CN F F H H
C2H5 CN F F H H
n-C3H7 CN F F H H
n-C4H9 CN F F H H
n-C5H11 CN F F H H
n-C6H13 CN F F H H
H F H H F H
CH3 F H H F H
R1 X L1 L2 L3 L4
C2H5 F H H F H
C3H7 F H H F H
n-C4H9 F H H F H
n-C5H11 F H H F H
n-C6H13 F H H F H
H F F H F H
CH3 F F H F H
C2H5 F F H F H
n-C3H7 F F H F H
n-C4H9 F F H F H
n-C5H11 F F H F H
n-C6H13 F F H F H
H F F F F H
CH3 F F F F H
C2H5 F F F F H
n-C3H7 F F F F H C 98 N 193.0 I;
Δε=37.9;Δn=0.1649
n-C4H9 F F F F H
n-C5H11 F F F F H
n-C6H13 F F F F H
H Cl H H F H
CH3 Cl H H F H
C2H5 Cl H H F H
n-C3H7 Cl H H F H
n-C4H9 Cl H H F H
n-C5H11 Cl H H F H
n-C6H13 Cl H H F H
H Cl F H F H
CH3 Cl F H F H
C2H5 Cl F H F H
n-C3H7 Cl F H F H
n-C4H9 Cl F H F H
n-C5H11 Cl F H F H
n-C6H13 Cl F H F H
H Cl F F F H
R1 X L1 L2 L3 L4
CH3 Cl F F F H
C2H5 Cl F F F H
n-C3H7 Cl F F F H
n-C4H9 Cl F F F H
n-C5H11 Cl F F F H
n-C6H13 Cl F F F H
H OCF3 H H F H
CH3 OCF3 H H F H
C2H5 OCF3 H H F H
n-C3H7 OCF3 H H F H
n-C4H9 OCF3 H H F H
n-C5H11 OCF3 H H F H
n-C6H13 OCF3 H H F H
H OCF3 F H F H
CH3 OCF3 F H F H
C2H5 OCF3 F H F H
n-C3H7 OCF3 F H F H
n-C4H9 OCF3 F H F H
n-C5H11 OCF3 F H F H
n-C6H13 OCF3 F H F H
H OCF3 F F F H
CH3 OCF3 F F F H
C2H5 OCF3 F F F H
n-C3H7 OCF3 F F F H
n-C4H9 OCF3 F F F H
n-C5H11 OCF3 F F F H
n-C6H13 OCF3 F F F H
H OCHF2 H H F H
CH3 OCHF2 H H F H
C2H5 OCHF2 H H F H
n-C3H7 OCHF2 H H F H
n-C4H9 OCHF2 H H F H
n-C5H11 OCHF2 H H F H
n-C6H13 OCHF2 H H F H
H OCHF2 F H F H
R1 X L1 L2 L3 L4
CH3 OCHF2 F H F H
C2H5 OCHF2 F H F H
n-C3H7 OCHF2 F H F H
n-C4H9 OCHF2 F H F H
n-C5H11 OCHF2 F H F H
n-C6H13 OCHF2 F H F H
H OCHF2 F F F H
CH3 OCHF2 F F F H
C2H5 OCHF2 F F F H
n-C3H7 OCHF2 F F F H
n-C4H9 OCHF2 F F F H
n-C5H11 OCHF2 F F F H
n-C6H13 OCHF2 F F F H
H OCHFCF3 H H F H
CH3 OCHFCF3 H H F H
C2H5 OCHFCF3 H H F H
n-C3H7 OCHFCF3 H H F H
n-C4H9 OCHFCF3 H H F H
n-C5H11 OCHFCF3 H H F H
n-C6H13 OCHFCF3 H H F H
H OCHFCF3 F H F H
CH3 OCHFCF3 F H F H
C2H5 OCHFCF3 F H F H
n-C3H7 OCHFCF3 F H F H
n-C4H9 OCHFCF3 F H F H
n-C5H11 OCHFCF3 F H F H
n-C6H13 OCHFCF3 F H F H
H OCHFCF3 F F F H
CH3 OCHFCF3 F F F H
C2H5 OCHFCF3 F F F H
n-C3H7 OCHFCF3 F F F H
n-C4H9 OCHFCF3 F F F H
n-C5H11 OCHFCF3 F F F H
n-C6H13 OCHFCF3 F F F H
H OCHFCF3 H H F H
R1 X L1 L2 L3 L4
CH3 OCHFCF3 H H F H
C2H5 OCHFCF3 H H F H
n-C3H7 OCHFCF3 H H F H
n-C4H9 OCHFCF3 H H F H
n-C5H11 OCHFCF3 H H F H
n-C6H13 OCHFCF3 H H F H
H OCHFCF3 F H F H
CH3 OCHFCF3 F H F H
C2H5 OCHFCF3 F H F H
n-C3H7 OCHFCF3 F H F H
n-C4H9 OCHFCF3 F H F H
n-C5H11 OCHFCF3 F H F H
n-C6H13 OCHFCF3 F H F H
H OCHFCF3 F F F H
CH3 OCHFCF3 F F F H
C2H5 OCHFCF3 F F F H
n-C3H7 OCHFCF3 F F F H
n-C4H9 OCHFCF3 F F F H
n-C5H11 OCHFCF3 F F F H
n-C6H13 OCHFCF3 F F F H
H OCF2CHFCF3 H H F H
CH3 OCF2CHFCF3 H H F H
C2H5 OCF2CHFCF3 H H F H
n-C3H7 OCF2CHFCF3 H H F H
n-C4H9 OCF2CHFCF3 H H F H
n-C5H11 OCF2CHFCF3 H H F H
n-C6H13 OCF2CHFCF3 H H F H
H OCF2CHFCF3 F H F H
CH3 OCF2CHFCF3 F H F H
C2H5 OCF2CHFCF3 F H F H
n-C3H7 OCF2CHFCF3 F H F H
n-C4H9 OCF2CHFCF3 F H F H
n-C5H11 OCF2CHFCF3 F H F H
n-C6H13 OCF2CHFCF3 F H F H
H OCF2CHFCF3 F F F H
R1 X L1 L2 L3 L4
CH3 OCF2CHFCF3 F F F H
C2H5 OCF2CHFCF3 F F F H
n-C3H7 OCF2CHFCF3 F F F H
n-C4H9 OCF2CHFCF3 F F F H
n-C5H11 OCF2CHFCF3 F F F H
n-C6H13 OCF2CHFCF3 F F F H
H NCS H H F H
CH3 NCS H H F H
C2H5 NCS H H F H
n-C3H7 NCS H H F H
n-C4H9 NCS H H F H
n-C5H11 NCS H H F H
n-C6H13 NCS H H F H
H NCS F H F H
CH3 NCS F H F H
C2H5 NCS F H F H
n-C3H7 NCS F H F H
n-C4H9 NCS F H F H
n-C5H11 NCS F H F H
n-C6H13 NCS F H F H
H NCS F F F H
CH3 NCS F F F H
C2H5 NCS F F F H
n-C3H7 NCS F F F H
n-C4H9 NCS F F F H
n-C5H11 NCS F F F H
n-C6H13 NCS F F F H
H C2F5 H H F H
CH3 C2F5 H H F H
C2H5 C2F5 H H F H
n-C3H7 C2F5 H H F H
n-C4H9 C2F5 H H F H
n-C5H11 C2F5 H H F H
n-C6H13 C2F5 H H F H
H C2F5 F H F H
R1 X L1 L2 L3 L4
CH3 C2F5 F H F H
C2H5 C2F5 F H F H
n-C3H7 C2F5 F H F H
n-C4H9 C2F5 F H F H
n-C5H11 C2F5 F H F H
n-C6H13 C2F5 F H F H
H C2F5 F F F H
CH3 C2F5 F F F H
C2H5 C2F5 F F F H
n-C3H7 C2F5 F F F H
n-C4H9 C2F5 F F F H
n-C5H11 C2F5 F F F H
n-C6H13 C2F5 F F F H
H C3F7 H H F H
CH3 C3F7 H H F H
C2H5 C3F7 H H F H
n-C3H7 C3F7 H H F H
n-C4H9 C3F7 H H F H
n-C5H11 C3F7 H H F H
n-C6H13 C3F7 H H F H
H C3F7 F H F H
CH3 C3F7 F H F H
C2H5 C3F7 F H F H
n-C3H7 C3F7 F H F H
n-C4H9 C3F7 F H F H
n-C5H11 C3F7 F H F H
n-C6H13 C3F7 F H F H
H C3F7 F F F H
CH3 C3F7 F F F H
C2H5 C3F7 F F F H
n-C3H7 C3F7 F F F H
n-C4H9 C3F7 F F F H
n-C5H11 C3F7 F F F H
n-C6H13 C3H7 F F F H
H SF5 H H F H
R1 X L1 L2 L3 L4
CH3 SF5 H H F H
C2H5 SF5 H H F H
n-C3H7 SF5 H H F H
n-C4H9 SF5 H H F H
n-C5H11 SF5 H H F H
n-C6H13 SF5 H H F H
H SF5 F H F H
CH3 SF5 F H F H
C2H5 SF5 F H F H
n-C3H7 SF5 F H F H
n-C4H9 SF5 F H F H
n-C5H11 SF5 F H F H
n-C6H13 SF5 F H F H
H SF5 F F F H
CH3 SF5 F F F H
C2H5 SF5 F F F H
n-C3H7 SF5 F F F H
n-C4H9 SF5 F F F H
n-C5H11 SF5 F F F H
n-C6H13 SF5 F F F H
H CN H H F H
CH3 CN H H F H
C2H5 CN H H F H
n-C3H7 CN H H F H
n-C4H9 CN H H F H
n-C5H11 CN H H F H
n-C6H13 CN H H F H
H CN F H F H
CH3 CN F H F H
C2H5 CN F H F H
n-C3H7 CN F H F H
n-C4H9 CN F H F H
n-C5H11 CN F H F H
n-C6H13 CN F H F H
H CN F F F H
R1 X L1 L2 L3 L4
CH3 CN F F F H
C2H5 CN F F F H
n-C3H7 CN F F F H
n-C4H9 CN F F F H
n-C5H11 CN F F F H
n-C6H13 CN F F F H
H F H H F F
CH3 F H H F F
C2H5 F H H F F
n-C4H9 F H H F F
n-C5H11 F H H F F
n-C6H13 F H H F F
H F F H F F
CH3 F F H F F
C2H5 F F H F F
n-C3H7 F F H F F
n-C4H9 F F H F F
n-C5H11 F F H F F
n-C6H13 F F H F F
H F F F F F
CH3 F F F F F
C2H5 F F F F F
C2H5 F F F F F
n-C3H7 F F F F F C 144 N 181.4 I;
Δε=42.1;Δn=0.1510
n-C4H9 F F F F F
n-C5H11 F F F F F
n-C6H13 F F F F F
H Cl H H F F
CH3 Cl H H F F
C2H5 Cl H H F F
n-C3H7 Cl H H F F
n-C4H9 Cl H H F F
n-C5H11 Cl H H F F
n-C6H13 Cl H H F F
R1 X L1 L2 L3 L4
H Cl F H F F
CH3 Cl F H F F
C2H5 Cl F H F F
n-C3H7 Cl F H F F
n-C4H9 Cl F H F F
n-C5H11 Cl F H F F
n-C6H13 Cl F H F F
H Cl F F F F
CH3 Cl F F F F
C2H5 Cl F F F F
n-C3H7 Cl F F F F
n-C4H9 Cl F F F F
n-C5H11 Cl F F F F
n-C6H13 Cl F F F F
H OCF3 H H F F
CH3 OCF3 H H F F
C2H5 OCF3 H H F F
n-C3H7 OCF3 H H F F
n-C4H9 OCF3 H H F F
n-C5H11 OCF3 H H F F
n-C6H13 OCF3 H H F F
H OCF3 F H F F
CH3 OCF3 F H F F
C2H5 OCF3 F H F F
n-C3H7 OCF3 F H F F C 121 N 205.2 I;
Δε=37.7;Δn=0.1634
n-C4H9 OCF3 F H F F
n-C5H11 OCF3 F H F F
n-C6H13 OCF3 F H F F
H OCF3 F F F F
CH3 OCF3 F F F F
C2H5 OCF3 F F F F
n-C3H7 OCF3 F F F F C 128 N 201.2 I;
Δε=43.8;Δn=0.1411
n-C4H9 OCF3 F F F F
R1 X L1 L2 L3 L4
n-C5H11 OCF3 F F F F
n-C6H13 OCF3 F F F F
H OCHF2 H H F F
CH3 OCHF2 H H F F
C2H5 OCHF2 H H F F
n-C3H7 OCHF2 H H F F
n-C4H9 OCHF2 H H F F
n-C5H11 OCHF2 H H F F
n-C6H13 OCHF2 H H F F
H OCHF2 F H F F
CH3 OCHF2 F H F F
C2H5 OCHF2 F H F F
n-C3H7 OCHF2 F H F F
n-C4H9 OCHF2 F H F F
n-C5H11 OCHF2 F H F F
n-C6H13 OCHF2 F H F F
H OCHF2 F F F F
CH3 OCHF2 F F F F
C2H5 OCHF2 F F F F
n-C3H7 OCHF2 F F F F
n-C4H9 OCHF2 F F F F
n-C5H11 OCHF2 F F F F
n-C6H13 OCHF2 F F F F
H OCHFCF3 H H F F
CH3 OCHFCF3 H H F F
C2H5 OCHFCF3 H H F F
n-C3H7 OCHFCF3 H H F F
n-C4H9 OCHFCF3 H H F F
n-C5H11 OCHFCF3 H H F F
n-C6H13 OCHFCF3 H H F F
H OCHFCF3 F H F F
CH3 OCHFCF3 F H F F
C2H5 OCHFCF3 F H F F
n-C3H7 OCHFCF3 F H F F
n-C4H9 OCHFCF3 F H F F
R1 X L1 L2 L3 L4
n-C5H11 OCHFCF3 F H F F
n-C6H13 OCHFCF3 F H F F
H OCHFCF3 F F F F
CH3 OCHFCF3 F F F F
C2H5 OCHFCF3 F F F F
n-C3H7 OCHFCF3 F F F F
n-C4H9 OCHFCF3 F F F F
n-C5H11 OCHFCF3 F F F F
n-C6H13 OCHFCF3 F F F F
H OCHFCF3 H H F F
CH3 OCHFCF3 H H F F
C2H5 OCHFCF3 H H F F
n-C3H7 OCHFCF3 H H F F
n-C4H9 OCHFCF3 H H F F
n-C5H11 OCHFCF3 H H F F
n-C6H13 OCHFCF3 H H F F
H OCHFCF3 F H F F
CH3 OCHFCF3 F H F F
C2H5 OCHFCF3 F H F F
n-C3H7 OCHFCF3 F H F F
n-C4H9 OCHFCF3 F H F F
n-C5H11 OCHFCF3 F H F F
n-C6H13 OCHFCF3 F H F F
H OCHFCF3 F F F F
CH3 OCHFCF3 F F F F
C2H5 OCHFCF3 F F F F
n-C3H7 OCHFCF3 F F F F
n-C4H9 OCHFCF3 F F F F
n-C5H11 OCHFCF3 F F F F
n-C6H13 OCHFCF3 F F F F
H OCF2CHFCF3 H H F F
CH3 OCF2CHFCF3 H H F F
C2H5 OCF2CHFCF3 H H F F
n-C3H7 OCF2CHFCF3 H H F F
n-C4H9 OCF2CHFCF3 H H F F
R1 X L1 L2 L3 L4
n-C5H11 OCF2CHFCF3 H H F F
n-C6H13 OCF2CHFCF3 H H F F
H OCF2CHFCF3 F H F F
CH3 OCF2CHFCF3 F H F F
C2H5 OCF2CHFCF3 F H F F
n-C3H7 OCF2CHFCF3 F H F F
n-C4H9 OCF2CHFCF3 F H F F
n-C5H11 OCF2CHFCF3 F H F F
n-C6H13 OCF2CHFCF3 F H F F
H OCF2CHFCF3 F F F F
CH3 OCF2CHFCF3 F F F F
C2H5 OCF2CHFCF3 F F F F
n-C3H7 OCF2CHFCF3 F F F F
n-C4H9 OCF2CHFCF3 F F F F
n-C5H11 OCF2CHFCF3 F F F F
n-C6H13 OCF2CHFCF3 F F F F
H NCS H H F F
CH3 NCS H H F F
C2H5 NCS H H F F
n-C3H7 NCS H H F F
n-C4H9 NCS H H F F
n-C5H11 NCS H H F F
n-C6H13 NCS H H F F
H NCS F H F F
CH3 NCS F H F F
C2H5 NCS F H F F
n-C3H7 NCS F H F F
n-C4H9 NCS F H F F
n-C5H11 NCS F H F F
n-C6H13 NCS F H F F
H NCS F F F F
CH3 NCS F F F F
C2H5 NCS F F F F
n-C3H7 NCS F F F F
n-C4H9 NCS F F F F
R1 X L1 L2 L3 L4
n-C5H11 NCS F F F F
n-C6H13 NCS F F F F
H C2F5 H H F F
CH3 C2F5 H H F F
C2H5 C2F5 H H F F
n-C3H7 C2F5 H H F F
n-C4H9 C2F5 H H F F
n-C5H11 C2F5 H H F F
n-C6H13 C2F5 H H F F
H C2F5 F H F F
CH3 C2F5 F H F F
C2H5 C2F5 F H F F
n-C3H7 C2F5 F H F F
n-C4H9 C2F5 F H F F
n-C5H11 C2F5 F H F F
n-C6H13 C2F5 F H F F
H C2F5 F F F F
CH3 C2F5 F F F F
C2H5 C2F5 F F F F
n-C3H7 C2F5 F F F F
n-C4H9 C2F5 F F F F
n-C5H11 C2F5 F F F F
n-C6H13 C2F5 F F F F
H C3F7 H H F F
CH3 C3F7 H H F F
C2H5 C3F7 H H F F
n-C3H7 C3F7 H H F F
n-C4H9 C3F7 H H F F
n-C5H11 C3F7 H H F F
n-C6H13 C3F7 H H F F
H C3F7 F H F F
CH3 C3F7 F H F F
C2H5 C3F7 F H F F
n-C3H7 C3F7 F H F F
n-C4H9 C3F7 F H F F
R1 X L1 L2 L3 L4
n-C5H11 C3F7 F H F F
n-C6H13 C3F7 F H F F
H C3F7 F F F F
CH3 C3F7 F F F F
C2H5 C3F7 F F F F
n-C3H7 C3F7 F F F F
n-C4H9 C3F7 F F F F
n-C5H11 C3F7 F F F F
n-C6H13 C3F7 F F F F
H SF5 H H F F
CH3 SF5 H H F F
C2H5 SF5 H H F F
n-C3H7 SF5 H H F F
n-C4H9 SF5 H H F F
n-C5H11 SF5 H H F F
n-C6H13 SF5 H H F F
H SF5 F H F F
CH3 SF5 F H F F
C2H5 SF5 F H F F
n-C3H7 SF5 F H F F
n-C4H9 SF5 F H F F
n-C5H11 SF5 F H F F
n-C6H13 SF5 F H F F
H SF5 F F F F
CH3 SF5 F F F F
C2H5 SF5 F F F F
n-C3H7 SF5 F F F F
n-C4H9 SF5 F F F F
n-C5H11 SF5 F F F F
n-C6H13 SF5 F F F F
H CN H H F F
CH3 CN H H F F
C2H5 CN H H F F
n-C3H7 CN H H F F
n-C4H9 CN H H F F
R1 X L1 L2 L3 L4
n-C5H11 CN H H F F
n-C6H13 CN H H F F
H CN F H F F
CH3 CN F H F F
C2H5 CN F H F F
n-C3H7 CN F H F F
n-C4H9 CN F H F F
n-C5H11 CN F H F F
n-C6H13 CN F H F F
H CN F F F F
CH3 CN F F F F
C2H5 CN F F F F
n-C3H7 CN F F F F
n-C4H9 CN F F F F
n-C5H11 CN F F F F
n-C6H13 CN F F F F
H CF3 H H F F
C2H5 CF3 H H F F
n-C3H7 CF3 H H F F
n-C4H9 CF3 H H F F
n-C5H11 CF3 H H F F
n-C6H13 CF3 H H F F
CH2=CH CF3 H H F F
H CF3 F F F F
C2H5 CF3 F F F F
n-C3H7 CF3 F F F F
n-C4H9 CF3 F F F F
n-C5H11 CF3 F F F F
n-C6H13 CF3 F F F F
CH2=CH CF3 F F F F
H F H H F F
C2H5 F H H F F
n-C3H7 F H H F F
n-C4H9 F H H F F
n-C5H11 F H H F F
R1 X L1 L2 L3 L4
n-C6H13 F H H F F
CH2=CH F H H F F
实施例6
以下化合物的对映异构体的分离:
为了分离对映异构体,让8.7g的T通过制备enantio-HPLC柱。在获得两个级分之后,各级分从乙醇中重结晶并测定它们的旋光度。
3.18g enantio-HPLC:99.68%-旋光度:+29.0°
3.74g enantio-HPLC:98.25%-旋光度:-28.0°
下列外消旋体通过类似方法被分离成对映异构体:
混合物实施例
实施例M1
CCH-5CF3 33.00% 澄清点[℃]: +80.0
CCP-1F.F.F 3.00% Δn[589nm,20℃]: +0.0660
CCP-2F.F.F 8.00% Δε[kHz,20℃]: +10.4
CCP-3F.F.F 8.00% d·Δn[20℃,μm]: 0.50
CCP-5F.F.F 5.00% 扭曲[°]: 90
CCP-20CF3.F 8.00% V10[V]: 1.31
CCP-50CF3.F 8.00%
CCOC-3-3 2.00%
CCOC-4-3 2.00%
CCQU-2-F 10.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
ACQU-3-F 15.00%
CCH-301 3.00%
CCH-501 5.00%
实施例M2
CCH-501 7.00% 澄清点[℃]: +88.5
CCH-5CF3 7.00% Δn[589nm,20℃]: +0.0657
CCP-2F.F.F 4.00% Δε[kHz,20℃]: +9.9
CCP-3F.F.F 7.00% d·Δn[20℃,μm]: 0.50
CCP-5F.F.F 5.00% 扭曲[°]: 90
CCP-30CF3.F 8.00% V10[V]: 1.45
CCP-50CF3.F 8.00%
CCOC-3-3 3.00%
CCOC-3-5 2.00%
CCOC-4-3 4.00%
CCQU-2-F 10.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
ACQU-3-F 15.00%
实施例M3
CCH-301 7.00% 澄清点[℃]: +81.0
CCH-501 10.00% Δn [589nm,20℃]: +0.0608
CCH-5CF3 2.00% Δε[kHz,20℃]: +8.4
CCP-2F.F.F 9.00% d·Δn[20℃,μm]: 0.50
CCP-3F.F.F 4.00% 扭曲[°]: 90
CCP-5F.F.F 4.00% V10[V]: 1.49
CCP-30CF3.F 2.00%
CCP-50CF3.F 4.00%
CCOC-3-3 3.00%
CCOC-3-5 2.00%
CCOC-4-3 4.00%
ACQU-3-F 15.00%
CCQU-2-F 10.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
CCH-35 4.00%
实施例M4
CCP-1F.F.F 4.00% 澄清点[℃]: +79.0
CCP-2F.F.F 10.00% Δn[589nm,20℃]: +0.0808
CCP-3F.F.F 9.00% Δε[kHz,20℃]: +15.5
CCP-5F.F.F 5.00% d·Δn[20℃,μm]: 0.50
CCP-30CF3.F 5.00% 扭曲[°]:90
CCP-50CF3.F 7.00% γ1[20℃,mPa·s]: 150
PUQU-2-F 5.00% V10[V]: 0.98
PUQU-3-F 5.00%
CCQU-2-F 11.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
CCGU-3-F 4.00%
ACQU-3-F 15.00%
实施例M5
BCH-3F.F 10.80% 澄清点[℃]: +89.0
BCH-5F.F 9.00% Δn[589nm,20℃]: +0.0930
ECCP-30CF3 4.50% Δε[kHz,20℃]: +6.2
ECCP-50CF3 4.50%
CBC-33F 1.80%
CBC-53F 1.80%
CBC-55F 1.80%
PCH-6F 7.20%
PCH-7F 5.40%
CCP-20CF3 7.20%
CCP-30CF3 10.80%
CCP-40CF3 6.30%
CCP-50CF3 9.90%
PCH-5F 9.00%
ACQU-3-F 10.00%
实施例M6
CCH-35 3.00% 澄清点[℃]: +81.0
CC-3-V1 4.00% Δn[589nm,20℃]: +0.0912
CCP-1F.F.F 10.00% d·Δn[20℃,μm]: 0.50
CCP-2F.F.F 9.00% 扭曲[°]: 90
CCP-3F.F.F 9.00% γ1[20℃,mPa·s]: 129
CCP-20CF3.F 6.00% V10[V]: 1.30
CCG-V-F 9.00%
CCP-20CF3 8.00%
CCP-30CF3 8.00%
CCP-40CF3 6.00%
CCP-50CF3 7.00%
PUQU-2-F 5.00%
PUQU-3-F 7.00%
APUQU-2-F 4.50%
CGUQU-3-F 3.50%
CBC-33 1.00%
实施例M7
CCP-2F.F.F 11.00% 澄清点[℃]: +80.0
CCP-20CF3 7.00% Δn[589nm,20℃]: +0.1034
CCP-30CF3 8.00% d·Δn[20℃,μm]: 0.50
CCP-40CF3 5.00% 扭曲[°]: 90
PGU-2-F 8.00% V10[V]: 1.22
PGU-3-F 7.00%
CC-3-V1 10.00%
CCH-35 3.00%
CCP-V-1 5.00%
CCP-20CF3.F 8.00%
CCP-30CF3.F 11.00%
PUQU-2-F 4.00%
PUQU-3-F 6.00%
ACQU-3-F 7.00%
实施例M8
CCP-1F.F.F 6.00% S→N[℃]: -40.0
CCP-2F.F.F 10.00% 澄清点[℃]: +80.0
CCP-20CF3 8.00% Δn[589nm,20℃]: +0.1029
CCP-30CF3 8.00% d·Δn[20℃,μm]: 0.50
CCP-40CF3 6.00% 扭曲[°]: 90
CCP-50CF3 8.00% V10[V]: 1.24
PGU-2-F 8.00%
PGU-3-F 7.00%
CC-3-V1 8.00%
CCH-35 5.00%
CCP-V-1 5.00%
CCP-30CF3.F 3.00%
PUQU-2-F 4.00%
PUQU-3-F 6.00%
ACQU-3-F 8.00%
实施例M9
CC-3-V1 5.00% S→N[℃]: -30.0
CCP-1F.F.F 5.00% 澄清点[℃]: +85.5
CCP-2F.F.F 8.00% Δn[589nm,20℃]: +0.0931
CCP-20CF3.F 8.00% Δε[kHz,20℃]: 12.1
CCP-20CF3 5.00% γ1[20℃,mPa·s]: 135
CCP-30CF3 8.00% d·Δn[20℃,μm]: 0.50
CCP-40CF3 6.00% 扭曲[°]: 90
CCP-50CF3 8.00% V10[V]: 1.23
PUQU-2-F 5.00%
PUQU-3-F 7.00%
PGU-2-F 5.00%
CCP-V-1 10.00%
ACQU-3-F 12.00%
ACQU-4-F 8.00%
实施例M10
CC-3-V1 6.00% S→N[℃]: -40.0
CCP-1F.F.F 6.00% 澄清点[℃]: +83.5
CCP-2F.F.F 7.00% Δn[589nm,20℃]: +0.0917
CCP-20CF3.F 10.00% Δε[kHz,20℃]: 11.7
CCP-20CF3 8.00% γ1[20℃,mPa·s]: 125
CCP-30CF3 8.00% d·Δn[20℃,μm]: 0.50
CCP-40CF3 6.00% 扭曲[°]: 90
CCP-50CF3 4.00% V10[V]: 1.25
PUQU-2-F 5.00%
PUQU-3-F 8.00%
PGU-2-F 4.00%
CCP-V-1 10.00%
ACQU-3-F 10.00%
ACQU-4-F 8.00%
实施例m11(IPS)
CDU-2-F 5.00% 澄清点[℃]: +81
PGU-2-F 2.50% Δn[589nm,20℃]: +0.0850
CCZU-2-F 4.00% Δε[kHz,20℃]: 10.1
CCZU-3-F 11.00% γ1[20℃,mPa·s]: 98
CCP-V-1 15.00%
CCQU-3-F 10.00%
PUQU-2-F 4.00%
PUQU-3-F 5.00%
CC-3-V1 11.00%
PCH-302 3.50%
CC-5-V 11.00%
ACQU-3-F 9.00%
ACQU-4-F 9.00%
实施例M12(IPS)
PGU-2-F 9.00% 澄清点[℃]: 81.0
PGU-3-F 2.00% Δn[589nm,20℃]: 0.1090
CGZP-2-OT 8.00% Δε[kHz,20℃]: 11.0
CGZP-3-OT 10.00% γ1[20℃,mPa·s]: 100
CCP-20CF3 6.00%
CCP-30CF3 6.50%
PUQU-2-F 4.00%
PUQU-3-F 3.50%
CCP-V-1 9.00%
CC-3-V1 11.00%
PCH-302 15.00%
ACQU-3-F 8.00%
ACQU-4-F 8.00%
实施例M13
CC-4-V 17.00% 澄清点[℃]: 74.5
CC-3-V1 3.00% Δn[589nm,20℃]: +0.0890
CCQU-2-F 12.00% Δε[kHz,20℃]: 12.7
CCQU-3-F 12.00% γ1[20℃,mPa·s]: 119
CCQU-5-F 10.00% V10[V]: 1.09
CCP-20CF3 5.00%
PGU-2-F 3.00%
PGU-3-F 6.00%
AUUQGU-3-F 8.00%
CCP-1F.F.F 8.00%
CCP-3F.F.F 9.00%
BCH-3F.F.F 7.00%
实施例M14
CC-3-V1 6.00% S→N [℃]: <-40.0
CCP-1F.F.F 9.00% 澄清点:[℃]: 83.5
CCP-2F.F.F 9.00% Δn[589nm,20℃]: 0.0941
CCP-3F.F.F 10.00% Δε[kHz,20℃]: 11.4
CCQU-3-F 11.00% γ1[20℃,mPa·s]: 137
CCQU-5-F 9.00% V10[V]: 1.23
CCP-20CF3 6.00%
CCP-30CF3 8.00%
CCP-50CF3 2.00%
CGU-2-F 4.00%
PGU-2-F 6.00%
PGU-3-F 6.00%
CCP-V-1 7.00%
ACQU-3-F 7.00%
实施例M15
CC-3-V1 5.00% S→N [℃]: <-40.0
CCP-1F.F.F 7.00% 澄清点[℃]: 84.0
CCP-2F.F.F 10.00% Δn[589nm,20℃]: 0.0919
ACQU-1-F 8.00% Δε[kHz,20℃]: 11.9
ACQU-3-F 8.00% γ1[20℃,mPa·s]: 135
CCG-V-F 11.00% V10[V]: 1.19
BCH-3F.F 2.50%
CCP-20CF3 8.00%
CCP-30CF3 8.00%
CCP-40CF3 5.00%
CCP-V-1 8.00%
PUQU-2-F 5.50%
PUQU-3-F 8.00%
CCGU-3-F 6.00%
实施例M16
CC-3-V1 5.00%
CCP-1F.F.F 7.00%
CCP-2F.F.F 6.00%
CCQU-3-F 10.00%
CCG-V-F 6.00%
CCP-20CF3 8.00%
CCP-30CF3 8.00%
CCP-40CF3 6.00%
CCP-50CF3 8.00%
ACQU-2-F 6.00%
ACQU-3-F 6.00%
PUQU-2-F 5.00%
PUQU-3-F 7.00%
PGU-3-F 6.00%
CCP-V-1 6.00%
实施例M17
CCP-20CF3 8.00% S→N[℃]: <-30.0
CCP-30CF3 8.00% 澄清点[℃]: 75.0
CCP-40CF3 5.00% Δn[589nm,20℃]: 0.0858
PGU-2-F 5.00% Δε[kHz,20℃]: 13.3
PGU-3-F 5.00% γ1[20℃,mPa·s]: 152
CCP-1F.F.F 10.00% V10[V]: 1.07
CCP-2F.F.F 11.00%
CCP-3F.F.F 12.00%
CCZU-2-F 3.00%
CCZU-3-F 13.00%
ACQU-2-F 8.00%
ACQU-3-F 8.00%
ACQU-5-F 4.00%
实施例M18
CC-4-V 11.00% S→N [℃]: <-40.0
CDU-2-F 7.00% 澄清点[℃]: 76.5
CDU-3-F 8.00% Δn[589nm,20℃]: 0.0870
CDU-5-F 9.00% Δε[kHz,20℃]: 13.6
CCP-1F.F.F 8.50% γ1[20℃,mPa·s]: 146
CCP-20CF3 8.00% V10[V]: 1.09
CCP-30CF3 6.50%
PGU-2-F 3.00%
PGU-3-F 6.00%
CCGU-3-F 6.00%
CBC-33 3.00%
ACQU-2-F 8.00%
ACQU-3-F 8.00%
ACQU-5-F 8.00%
实施例M19
CC-4-V 10.00% S→N [℃]: <-40.0
CCP-1F.F.F 9.00% 澄清点[℃]: 75.0
CCP-2F.F.F 9.00% Δn[589nm,20℃]: 0.0869
CCP-30CF3.F 8.00% Δε[kHz,20℃]: 13.1
CCP-20CF3 8.00% γ1[20℃,mPa·s]: 128
CCP-30CF3 8.00% V10[V]: 1.06
ACQU-2-F 8.00%
ACQU-3-F 8.00%
ACQU-4-F 8.00%
PGU-2-F 2.00%
PUQU-2-F 5.00%
PUQU-3-F 8.00%
CCGU-3-F 6.00%
CBC-33 3.00%
实施例M20
CC-4-V 18.00% S→N [℃]: <-40.0
CC-3-V1 3.00% 澄清点[℃]: 75.0
CCQU-2-F 11.00% Δn[589nm,20℃]: 0.0891
CCQU-3-F 12.00% Δε[kHz,20℃]: 13.0
CCQU-5-F 8.00% γ1[20℃,mPa·s]: 113
CCP-20CF3 8.00% V10[V]: 1.08
PGU-2-F 2.00%
PGU-3-F 6.00%
APUQ U-2-F 8.00%
APUQU-3-F 9.00%
CCP-1F.F.F 7.00%
CCP-2F.F.F 7.00%
CCGU-3-F 1.00%
实施例M21
CC-4-V 17.00% S→N [℃]: <-40.0
PUQU-2-F 5.00% 澄清点[℃]: 75.5
PUQU-3-F 7.00% Δn[589nm,20℃]: 0.0894
CCP-20CF3 6.00% Δε[kHz,20℃]: 14.0
CCP-30CF3 5.00% γ1[20℃,mPa·s]: 120
CCP-2F.F.F 5.00% V10[V]: 1.06
CCZU-2-F 3.00%
CCZU-3-F 13.00%
PG U-3-F 6.00%
ACQU-1-F 8.00%
ACQU-3-F 8.00%
ACQU-4-F 8.00%
CCGU-3-F 6.00%
CBC-33 3.00%
实施例M22
CC-4-V 16.00% S→N[℃]: <-40.0
CC-3-V1 8.00% 澄清点[℃]: 75.5
CCP-1F.F.F 5.00% Δn[589nm,20℃]: 0.0916
CCP-2F.F.F 6.00% Δε[kHz,20℃]: 13.6
CCQU-2-F 10.00% γ1[20℃,mPa·s]: 107
CCQU-3-F 12.00% V10[V]: 1.08
CCP-20CF3 4.00%
CCZU-3-F 13.00%
PG U-2-F 5.00%
PGU-3-F 5.00%
APUQU-2-F 8.00%
APUQU-3-F 8.00%
实施例M23
CCP-1F.F.F 6.00% 澄清点[℃]: 78.2
CCP-2F.F.F 9.00% Δn[589nm,20℃]: 0.0791
CCP-3F.F.F 6.00% Δε[kHz,20℃]: 14.3
CCP-5F.F.F 4.00%
CCP-20CF3.F 5.00%
CCP-30CF3.F 5.00%
CCP-50CF3.F 7.00%
CDU-2-F 7.00%
CDU-3-F 10.00%
CDU-5-F 10.00%
CGU-3-F 4.00%
CCGU-3-F 9.00%
ACQU-3-F 18.00%
实施例M24
CCQU-2-F 13.00% 澄清点[℃]: 84.5
CCQU-3-F 14.00% Δn[589nm,20℃]: 0.0779
CCQU-5-F 13.00% Δε[kHz,20℃]: 18.7
ACQU-5-F 33.00% γ1[20℃,mPa·s]: 182
APUQU-2-F 7.00% V10[V]: 0.95
APUQU-3-F 9.00%
CC-4-V 11.00%
实施例M25
CC-4-V 18.00% 澄清点[℃]: 74.5
CC-3-V1 5.00% Δn[589nm,20℃]: 0.0882
CCP-2F.F.F 8.00% Δε[kHz,20℃]: 12.9
CCQU-2-F 9.00% γ1[20℃,mPa·s]: 103
CCQU-3-F 11.00% V10[V]: 1.09
CCQU-5-F 11.00%
CCQG-3-F 6.00%
BCH-3F.F.F 8.00%
APUQU-2-F 6.00%
APUQU-3-F 6.00%
PUQU-2-F 3.00%
PUQU-3-F 6.00%
CCGU-3-F 1.50%
PGP-2-3 1.50%
实施例M26(IPS)
CCP-20CF3 7.00% 澄清点[℃]: 80.0
CCP-30CF3 7.00% Δn[589nm,20℃]: 0.1102
CCP-40CF3 7.00% Δε[kHz,20℃]: 11.1
CCP-50CF3 3.50% γ1[20℃,mPa·s]: 82
CCZU-3-F 5.00% V10[V]: 1.13
PGU-2-F 9.00%
PGU-3-F 8.00%
PUQU-2-F 6.00%
PUQU-3-F 6.00%
CC-3-V1 13.00%
CC-4-V 14.00%
CCP-V-1 8.00%
APUQU-2-F 6.50%
实施例M27(IPS)
CCP-20CF3 8.00% 澄清点[℃]: 79.5
CCP-30CF3 8.00% Δn[589nm,20℃]: 0.1095
CCP-40CF3 8.00% Δε[kHz,20℃]: 11.4
CCZU-3-F 5.00% γ1[20℃,mPa·s]: 87
PGU-2-F 9.00% V10[V]: 1.11
PGU-3-F 8.50%
PUQU-2-F 6.00%
PUQU-3-F 5.00%
CC-3-V1 12.50%
CC-4-V 14.00%
CCP-V-1 9.00%
AGUQU-2-F 3.50%
AGUQU-3-F 3.50%
实施例M28(IPS)
CCP-2F.F.F 6.50% 澄清点[℃]: 78.0
CCP-30CF3 6.00% Δn[589nm,20℃]: 0.0805
CCZU-2-F 4.00% Δε[kHz,20℃]: 14.8
CCZU-3-F 15.00% γ1[20℃,mPa·s]: 121
CDU-2-F 9.00%
CDU-3-F 4.00%
CCQU-3-F 13.00%
CCQU-5-F 10.00%
PUQU-2-F 5.00%
PUQU-3-F 5.00%
APUQU-2-F 6.00%
CC-3-V1 12.00%
CC-4-V 4.50%
实施例28(IPS)
CDU-2-F 9.00% 澄清点[℃]: 76.5
CDU-3-F 8.00% Δn[589nm,20℃]: 0.0960
PGU-2-F 9.00% Δε[kHz,20℃]: 12.7
CCZU-2-F 4.00% γ1[20℃,mPa·s]: 92
CCZU-3-F 11.00% V10[V]: 1.02
PUQU-2-F 4.00%
PUQU-3-F 6.00%
APUQU-2-F 7.00%
CCP-V-1 14.50%
CC-3-V1 12.50%
CC-4-V 10.00%
CCH-35 5.00%
实施例M30(IPS)
CCP-30CF3 3.50% 澄清点[℃]: 75.5
CDU-2-F 5.00% Δn[589nm,20℃]: 0.0975
PGU-2-F 6.50% Δε[kHz,20℃]: 8.4
PUQU-2-F 8.00% γ1[20℃,mPa·s]: 67
PUQU-3-F 8.00% V10[V]: 1.28
CCP-V-1 13.00%
CCP-V2-1 9.50%
CC-3-V1 13.00%
CC-5-V 9.00%
CC-4-V 14.00%
PCH-302 3.50%
APUQU-2-F 7.00%
实施例M31(IPS)
PGU-2-F 6.50% 澄清点[℃]: 74.0
CDU-2-F 9.00% Δn[589nm,20℃]: 0.1005
PUQU-2-F 11.00% Δε[kHz,20℃]: 14.1
PUQU-3-F 10.00% γ1[20℃,mPa·s]: 92
CCP-30CF3 8.00%
CCZU-3-F 11.50%
CC-4-V 10.00%
CC-5-V 3.00%
CC-3-V1 11.00%
CCP-V2-1 13.00%
APUQU-2-F 7.00%
实施例M32
CCQU-2-F 10.00% 澄清点[℃]: 82.0
CCQU-3-F 12.00% Δn[589nm,20℃]: 0.0792
CCQU-5-F 8.00% Δε[kHz,20℃]: 11.2
CCP-1F.F.F 6.00% V10[V]: 1.20
CCP-2F.F.F 5.00%
CCP-3F.F.F 5.00%
CC-3-V1 10.00%
CC-4-V 14.00%
CGU-2-F 5.00%
CCGU-3-F 5.00%
ACQG-3-F 5.00%
ACQG-4-F 5.00%
APUQU-2-F 5.00%
APUQU-3-F 5.00%
实施例M33
CCQU-2-F 11.00% 澄清点[℃]: 81.5
CCQU-3-F 13.00% Δn[589nm,20℃]: 0.0804
CCQU-5-F 11.00% Δε[kHz,20℃]: 13.6
CCP-1F.F.F 8.00% γ1[20℃,mPa·s]: 153
CCP-2F.F.F 10.00% V10[V]: 1.06
CCP-3F.F.F 10.00%
CCP-5F.F.F 6.00%
CC-3-V1 9.00%
CGU-3-F 4.00%
ACQG-3-F 3.00%
ACQG-4-F 5.00%
APUQU-2-F 5.00%
APUQU-3-F 5.00%
实施例M34
CCH-5CF3 5.00% 澄清点[℃]: 80.5
CCP-1F.F.F 5.00% Δn[589nm,20℃]: 0.0660
CCP-2F.F.F 9.00% Δε[kHz,20℃]: 9.7
CCP-3F.F.F 8.00% V10[V]: 1.27
CCP-5F.F.F 5.00%
CCP-20CF3.F 6.00%
CCP-50CF3.F 6.00%
CCOC-3-3 2.00%
CCOC-4-3 2.00%
CCQU-2-F 10.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
CCH-501 6.00%
ACQG-3-F 8.00%
ACQG-4-F 8.00%
实施例M35
CCP-1F.F.F 7.00% 澄清点[℃]: 81.5
CCP-2F.F.F 8.00% Δn[589nm,20℃]: 0.0658
CCP-3F.F.F 7.00% Δε[kHz,20℃]: 13.5
CCP-5F.F.F 4.00% V10[V]: 1.06
CCQU-2-F 11.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
ACQU-2-F 8.00%
ACQU-3-F 9.00%
ACQU-5-F 8.00%
ACQG-3-F 7.00%
ACQG-4-F 5.00%
CCOC-3-3 3.00%
CCOC-4-3 3.00%
实施例M36
AUUQU-3-F 6.00% 澄清点[℃]: 98.0
AGUQU-3-F 6.00% Δn[589nm,20℃]: 0.0927
APUQU-2-F 6.00% Δε[kHz,20℃]: 18.9
CGU-2-F 5.00%
CGU-3-F 5.00%
CGU-5-F 5.00%
CCZU-2-F 5.50%
CCZU-3-F 10.50%
CCZU-5-F 5.50%
CCQU-2-F 10.00%
CCQU-3-F 10.00%
CCQU-5-F 10.00%
CC-5-V 9.50%
CCPC-33 2.00%
CCPC-34 2.00%
CCPC-35 2.00%
实施例M37
CCQU-2-F 7.00% 澄清点[℃]: 85.5
CCQU-3-F 8.00% Δn[589nm,20℃]: 0.0783
CCQU-5-F 8.00% Δε[kHz,20℃]: 11.66
CCQG-3-F 6.00% γ1[20℃,mPa·s]: 213
ACQU-2-F 17.00% V10[V]: 0.90
ACQU-5-F 16.00%
PUQU-2-F 5.00%
PUQU-3-F 5.00%
CCGU-3-F 5.00%
CCOC-4-3 3.00%
CCZU-2-F 3.00%
CCZU-3-F 14.00%
CCZU-5-F 3.00%
实施例M38
BCH-3F.F 10.80% 澄清点[℃]: 56.9
BCH-5F.F 9.00% Δn[589nm,20℃]: 0.0834
ECCP-30CF3 4.50% Δε[kHz,20℃]: 4.1
ECCP-50CF3 4.50% γ1[20℃,mPa·s]: 65
CBC-33F 1.80%
CBC-53F 1.80%
CBC-55F 1.80%
PCH-6F 7.20%
PCH-7F 5.40%
CCP-20CF3 7.20%
CCP-30CF3 10.80%
CCP-40CF3 6.30%
CCP-50CF3 9.90%
PCH-5F 9.00%
AUUQPU-3-F 10.00%
实施例M39
CCP-1F.F.F 3.00% 澄清点[℃]: 79.5
CCP-2F.F.F 6.00% Δn[589nm,20℃]: 0.0796
CCP-3F.F.F 7.00% Δε[kHz,20℃]: 10.12
CCP-5F.F.F 5.00% γ1[20℃,mPa·s]: 202
CCQU-2-F 11.00% V10[V]: 0.93
CCQU-3-F 12.00%
CCQU-5-F 8.00%
CGU-2-F 4.00%
CGU-3-F 7.00%
CCGU-3-F 9.00%
ACQU-2-F 8.00%
ACQU-3-F 10.00%
ACQU-4-F 10.00%
实施例M40
CCH-5CF3 2.00% 澄清点[℃]: 79.5
CCP-2F.F.F 9.00% Δn[589nm,20℃]: 0.0659
CCP-3F.F.F 7.00% Δε[kHz,20℃]: 8.22
CCP-5F.F.F 4.00% γ1[20℃,mPa·s]: 169
CCP-20CF3.F 7.00% V10[V]: 1.14
CCP-50CF3.F 6.00%
CCOC-3-3 2.00%
CCOC-4-3 2.00%
CCQU-2-F 10.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
ACQU-2-F 8.00%
ACQU-3-F 10.00%
ACQU-4-F 8.00%
CCH-501 5.00%
实施例M41
CCP-1F.F.F 6.00% 澄清点[℃]: 80.0
CCP-2F.F.F 9.00% Δn[589nm,20℃]: 0.0694
CCP-3F.F.F 10.00% Δε[kHz,20℃]: 8.96
CCP-5F.F.F 6.00% γ1[20℃,mPa·s]: 175
CCP-20CF3.F 4.00% V10[V]: 1.11
CCP-50CF3.F 8.00%
CCQU-2-F 11.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
ACQU-3-F 26.00%
实施例M42
CCP-1F.F.F 8.00% 澄清点[℃]: 88.0
CCP-2F.F.F 7.00% Δn[589nm,20℃]: 0.0788
CCP-3F.F.F 9.00% Δε[kHz,20℃]: 8.51
CCP-5F.F.F 6.00% γ1[20℃,mPa·s]: 192
CCP-30CF3.F 9.00% V10[V]: 1.13
CCP-50CF3.F 9.00%
CGU-2-F 5.00%
CCGU-3-F 5.00%
CCQU-2-F 11.00%
CCQU-3-F 12.00%
CCQU-5-F 8.00%
ACQU-3-F 6.00%
ACQU-4-F 5.00%
实施例M43
CCP-1F.F.F 2.00% 澄清点[℃]: 81.0
CCP-20CF3 8.00% Δn[589nm,20℃]: 0.0785
CCP-30CF3 8.00% Δε[kHz,20℃]: 7.27
CCP-40CF3 6.00% γ1[20℃,mPa·s]: 108
CCP-50CF3 8.00% V10[V]: 1.34
CCP-20CF3.F 12.00%
ACQU-2-F 8.00%
ACQU-3-F 8.00%
ACQU-4-F 8.00%
PUQU-2-F 5.00%
PUQU-3-F 7.00%
CC-3-V1 8.00%
CC-4-V 9.00%
CCOC-4-3 3.00%
实施例M44
CC-3-V1 5.00% S→N[℃]: <20.0
CCP-1F.F.F 8.00% 澄清点[℃]: 82.5
CCP-2F.F.F 10.00% Δn[589nm,20℃]: 0.0939
CCQU-2-F 10.00% Δε[kHz,20℃]: 10.6
CCQU-3-F 5.00% γ1[20℃,mPa·s]: 128
CCP-20CF3 8.00% V10[V]: 1.19
CCP-30CF3 8.00%
CGU-2-F 9.00%
PGU-3-F 5.00%
CCP-V-1 6.00%
CCG-V-F 18.00%
APUQU-3-F 8.00%
实施例M45
CCP-2F.F.F 7.00% 澄清点[℃]: 88.0
CCP-3F.F.F 6.00% Δn[589nm,20℃]: 0.0720
CCP-5F.F.F 6.00% Δε[kHz,20℃]: 16.1
ACQU-2-F 10.00% γ1[20℃,mPa·s]:210
ACQU-3-F 10.00% V10[V]: 0.97
ACQU-5-F 11.00%
CCQU-2-F 10.00%
CCQU-3-F 12.00%
CCQU-5-F 10.00%
CCGU-3-F 5.00%
CCZU-2-F 4.00%
CCZU-3-F 9.00%
Claims (10)
1.结构式I的液晶化合物,
其中
R1和R2各自独立地表示H,卤素,具有1-15个碳原子的卤代或未取代的烷基或烷氧基,其中,另外在这些基团中的一个或多个CH2基团可以各自独立地被-C≡C-,-CH=CH-,-O-,-CO-O-或-O-CO-替代,但要求O原子不直接彼此连接,其中基团R1和R2中的一个可以另外表示CN,OCN,SCN,NCS或SF5,
A1,A2,A3和A4各自独立地表示:
Z1,Z2和Z3各自独立地表示-CO-O-,-O-CO-,-CF2O-,-OCF2-,-CH2O-,-OCH2-,-CH2CH2-,-(CH2)4-,-C2F4-,-CH2CF2-,-CF2CH2-,-CF=CF-,-CH=CH-,-C≡C-或单键,和
a,b和c各自独立地表示0,1,2或3,其中a+b+c≤3。
3.根据权利要求1或2的液晶化合物,其特征在于a=1和b=0或a=0和b=1。
4.根据权利要求2的液晶化合物,其特征在于L1表示氟和L2表示氟或氢。
5.根据权利要求2的液晶化合物,其特征在于L1和L2表示氟。
7.包括至少两种内消旋化合物的液晶介质,其特征在于它包括根据权利要求1的结构式I的至少一种化合物。
9.根据权利要求7或8的液晶介质在电光学应用中的用途。
10.含有根据权利要求7或8的液晶介质的电光学液晶显示器。
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- 2003-11-17 EP EP03811758A patent/EP1565540B1/de not_active Expired - Lifetime
- 2003-11-17 AU AU2003302394A patent/AU2003302394A1/en not_active Abandoned
- 2003-11-17 US US10/536,808 patent/US7291367B2/en not_active Expired - Lifetime
- 2003-11-26 TW TW092133171A patent/TWI320054B/zh not_active IP Right Cessation
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2011
- 2011-01-06 JP JP2011001377A patent/JP5314709B2/ja not_active Expired - Lifetime
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Also Published As
Publication number | Publication date |
---|---|
US20060061699A1 (en) | 2006-03-23 |
JP2011136998A (ja) | 2011-07-14 |
CN1717468A (zh) | 2006-01-04 |
DE10353658A1 (de) | 2004-06-09 |
ATE374232T1 (de) | 2007-10-15 |
DE50308290D1 (de) | 2007-11-08 |
KR101070102B1 (ko) | 2011-10-05 |
JP5314709B2 (ja) | 2013-10-16 |
JP4711392B2 (ja) | 2011-06-29 |
EP1565540B1 (de) | 2007-09-26 |
CN101294079B (zh) | 2013-06-19 |
TW200418961A (en) | 2004-10-01 |
AU2003302394A1 (en) | 2004-06-18 |
US7291367B2 (en) | 2007-11-06 |
KR20050086861A (ko) | 2005-08-30 |
JP2006508150A (ja) | 2006-03-09 |
EP1565540A1 (de) | 2005-08-24 |
WO2004048501A1 (de) | 2004-06-10 |
TWI320054B (en) | 2010-02-01 |
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