Supertwist liquid-.crystal display

Abstract: The invention relates to supertwist liquid-crystal displays (SFAs) having extremely short switching times and good steepnesses and angle dependencies, and to the novel nematic liquid-crystal mixtures used therein based on and/or one or more compounds of the formula II and/or one or more compounds of the formula III wherein R¹ is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH₂ groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, r is O or 1, s is O, 1 or 2, rings A¹ and A² are independently from each other trans-1,4-cyclohexylene, 1,4-phenylene or 3-fluoro-1,4-phenylene A³ denotes Q is OCFH, OCF₂, CF₂ or a single bond, Y is H, F or Cl, and L denotes H or F.

Description: The invention relates to supertwist liquid-crystal displays (SFAs) having extremely short switching times and good steepnesses and angle dependencies, and to the novel nematic liquid-crystal mixtures used therein. SFAs as in the heading are known, for example from EP 0,131,216 B1; DE 3,423,993 Al; EP 0,098,070 A2; M. Schadt and F. Leenhouts, 17th Freiburg conference on liquid crystals (8-10.04.87); K. Kawasaki et al., SID 87 Digest 391 (20.6); M. Schadt and F. Leenhouts, SID 87 Digest 372 (20.1); K. Katoh et al., Japanese Journal of Applied Physics, Vol. 26, No. 11, L 1784-L1786 (1987); F. Leenhouts et al., Appl. Phys. Lett. 50 (21), 1468 (1987); H.A. van Sprang and H.G. Koopman, J. Appl. Phys. 62 (5), 1734 (1987); T.J. Scheffer and J. Nehring, Appl. Phys. Lett. 45 (10), 1021 (1984), M. Schadt and F. Leenhouts, Appl. Phys. Lett. 50 (5), 236 (1987) and E.P. Raynes, Mol. Cryst. Liq. Cryst. Letters, Vol. 4 (1), pp. 1-8 (1986). The term SFA here includes any relatively highly twisted display element having a twist angle with a value between 160° and 720°, such as, for example, the display elements of Waters et al. (C.M. Waters et al., Proc. Soc. Inf. Disp. (New York) (1985) (3rd Intern. Display Conference, Kobe, Japan), the STN-LCDs (DE OS 3,503,259), SBE-LCDs (T.J. Scheffer and J. Nehring, Appl. Phys. Lett. 45 (1984) 1021), OMI-LCDs (M. Schadt and F. Leenhouts, Appl. Phys. Lett. 50 (1987), 236, DST-LCDs (EP OS 0,246,842) or BW-STN-LCDs (K. Kawasaki et al., SID 87 Digest 391 (20.6)). Compared with standard TN displays, SFAs of this type are distinguished by significantly better steepnesses of the electrooptical characteristic and, associated therewith, better contrast values, and by a significantly lower angle dependence of the contrast. Of particular interest are SFAs with extremely short switching times, in particular also at relatively low temperatures. In order to achieve short switching times,the viscosities, in particular of the liquid crystal mixtures have hitherto been optimized using usually optimized combinations of liquid crystal components and optionally also monotropic additives of relatively high vapour pressure. However, the switching times achieved were not adequate for all applications. Shorter switching times can also be achieved by reducing the thickness of LC layer of the SFA and using liquid-crystal mixtures with a higher birefringence Δn. All these approaches to shorter switching times, however, still end up with mixtures which were not adequate for every use. Further demands for SFA are a higher multiplexability (resulting in a smaller number of LC's), lower threshold voltages and a steep characteristic curve. Optimal parameters, however, cannot be achieved simultaneously for all the properties mentioned above because of opposite influence of different material parameters such as dielectric and elastic properties. In WO-A-8,908,692 WO-A-9 110 716 and WO-A-9 115 556 SFA's containing fluoro compounds of formula III are disclosed, however there is no hint to combinations of this compounds with phenylpyrimidines of formula B1VIII or with cyclohexanes. Therefore, there continues to be a great demand for improved SFAs having short switching times and, at the same time, a broad service-temperature range, high characteristic line steepness, good angle dependency of the contrast and low threshold voltage. The invention has the object of providing SFAs which only have the abovementioned disadvantages to a small extent, or not at all, and at the same time have very useful overall properties. It has now been found that this object can be achieved if nematic liquid-crystal mixtures are used which contain one or more compounds of the formula I and/or one or more compounds of the formula II and/or one or more compounds of the formula III wherein R 1 is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, r is 0 or 1, s is 0, 1 or 2, rings A 1 and A 2 are independently from each other trans-1,4-cyclohexylene, 1,4-phenylene or 3-fluoro-1,4-phenylene A 3 denotes Q is OCHF, OCF 2 , CF 2 or a single bond, Y is H, E or Cl and L denotes H or F. The nematic liquid-crystal mixture preferably has a nematic phase range of at least 60 °C, a viscosity of not more than 30 mPa.s and a dielectric anisotropy of at least +5, the dielectric anisotropies of the compounds and the parameters related to the nematic liquid-crystal mixture being based on a temperature of 20 °C. The invention thus relates to an SFA having two plane-parallel carrier plates which, with an edging, form a cell, a nematic liquid crystal mixture of positive dielectric anisotropy in the cell, electrode layers with superimposed orientation layers on the inside of the carrier plates, an angle of incidence between the longitudinal axis of the molecules on the surface of the carrier plates and the carrier plates of about 1 degree to 30 degrees and the absolute amount of the twisting angle of the liquid crystal mixture in the cell from orientation layer to orientation layer being between 160 and 720 °, characterized in that the nematic liquid crystal mixture contains one or more compounds of the formula I and/or one or more compounds of the formula II and/or one or more compounds of the formula III wherein R 1 is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, r is 0 or 1, s is 0, 1 or 2, rings A 1 and A 2 are independently from each other trans-1,4-cyclohexylene, 1,4-phenylene or 3-fluoro-1,4-phenylene, A 3 denotes Q is OCHF, OCF 2 , CF 2 or a single bond, Y is H, F, or Cl and L denotes H or F and at least one compound of the formula B1VIII in which R 1 and R 2 in each case independently of one another are alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, and or at least one compound of the formula in which R 1 is CH 3 -(CH 2 ) n -O-, CH 3 -(CH 2 ) t -, trans-H-(CH 2 ) r -CH=CH-(CH 2 CH 2 ) s -CH 2 -O-, trans-H-(CH 2 ) r -CH=CH-(CH 2 -CH 2 ) s -, R 2 is CH 3 -(CH 2 ) t -, n is 1, 2, 3 or 4, t is 1, 2, 3 or 4, r is 0, 1, 2 or 3, s is 0 or 1. In a special embodiment the SFA is characterized in that the nematic liquid crystal mixture contains one or more compounds of the formula III wherein R 1 is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, A 3 denotes Q is OCHF, OCF 2 or CF 2 , Y is H, F or Cl and L denotes H or F. The invention also relates to corresponding liquid-crystal mixtures. The individual compounds of the formulae I, II and III and also other compounds which can be used in the SFAs according to the invention, are either known or can be prepared analogously to the known compounds. The mixtures of this invention allow the realization of SFAs with high multiplex ratios, broad working temperature range, low threshold voltages (below 3 volt, preferably between 1.25 and 2.80, in particular between 1.60 and 2.20 volt) and steep characteristic curves. The compounds of the formulae I, II and III have low values of the ratio of the elastic constants (K 3 /K 1 ) and lead therefore to short switching times. The mixtures according to the present invention have an optic anisotropy (Δn) of more than 0.120, preferably 0.130-0.170, in particular 0.130-0.160. The mixtures according to the invention preferably contain one or more compounds selected from the following group: Preferred mixtures contain one, two, three or more compounds of the formulae If, IIId, IIIh, IIIi, IIII, IIIs, in particular one or more compounds of the formula IIId or IIIs and one or three compounds selected from the formulae If, IIIh, IIIi, IIIl, IIIt and IIIu. Preferred liquid-crystal mixtures which can be used according to the invention contain one or more compounds from group A preferably in a proportion of 5 % to 60 %, preferably 10 % to 40 %. These compounds or this compound from group A have a dielectric anisotropy of more than +8 (preferably of more than +12) and form the component A of the LC mixtures of this invention. Preferably group A comprises compounds selected from the following group: wherein R is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, Q is the formula Z 1 is a single bond, -CH 2 CH 2 -, -CO-O- or -O-CO- and Preferably the mixtures comprise one ore more compounds of the formula AI in the range of 5 to 60 %. Preferred are those compounds wherein Z 1 denotes a single bond, -CH 2 CH 2 - or -CO-O- and especially preferred are the following compounds: Also preferred are the following compounds: Group A preferably comprises one ore more compounds selected from the formulae AI1 to AI5 and optionally also one or more compounds of the formula AI6. Preferably the mixtures further contain one or more polar compounds with a higher clearing point, e.g. selected from the following compounds: In the above four formulae the 1,4-phenylene rings can also be laterally substituted by one fluorine atom, e.g. These polar compounds with a higher clearing point are preferably used in the range of 2 to 15 %. In another preferred embodiment the mixtures comprise one or more compounds with a very high dielectric anisotropy. Such compounds are preferably used in the range of 2 to 60 %. Preferred compounds of this type are those of the formulae AII, AIII and AV, wherein Q denotes 1,4-phenylene or 3-fluoro-1,4-phenylene or compounds of the formula AI7: Preferred liquid-crystal mixtures contain one or more compounds from group B , preferably in a proportion of 10 % to 40 %. These compounds or this compound from group B have a clearing point of more than 120° and dielectrically neutral ((Δε) < 2) or medium polar (Δε in the range of +2 to +10, preferably +4 to +8) and form component B of the LC mixtures of this invention. Preferably group B comprises compounds selected from the following group: wherein R 1 and R 2 each independently of one another are R as defined in claim 4, Z o is -CO-O-, -O-CO- or -CH 2 CH 2 -, Q is as defined in claim 4 and the 1,4-phenylene ring in BI to BVII may also be substituted in 2- or 3-position by fluorine. Preferably the mixtures comprise one or more compounds with four rings of the formulae BI to BIV in order to achieve a high clearing point. These compounds are preferably selected from the group of the following four-ring compounds: Preferably the mixtures comprise also one or more compounds selected from the following group of three-ring compounds: In another preferred embodiment the LC mixtures also contain one or more compounds from the following group: wherein Hal is F or Cl and L and R are as defined above. The LC mixtures also comprise an optically active component C, in an amount such that the ratio between the layer thickness (separation of the plane-parallel carrier plates) and the natural pitch of the chiral nematic liquid crystal mixture is more than 0.2 suitable to the desired twist angle. Suitable dopants can be selected from a wide variety of known chiral materials and commercially available dopants such as cholesteryl nonanoate, S 811 (E. Merck, Darmstadt, FRG) and CB 15 (BDH, Poole, UK). The choice thereof is not crucial per se. Preferably the mixtures also contain one or more compounds from group B1 comprising the compounds of the formulae B1I to B1IV: in which R 1 and R 2 , in each case independently of one another, are as defined for R, Z 2 is -CH 2 CH 2 -, -CO-O-, -O-CO- or a single bond, and and/or at least one component selected from group B2 comprising the compounds of the formulae B1V to B1VII: in which R 1 is as defined for R, Z° is -CH 2 CH 2 - or a single bond, and Q is where n is 1 to 9, X is CN or F and Y is H or F; and/or at least one component selected from group B3 comprising the compounds of the formulae B1VIII, B1IX and B1X: in which R 1 and R 2 , in each case independently of one another, are as defined for R, X is Cl or F, and In a further preferred embodiment the LC mixtures contain one or more compounds selected from group T , comprising compounds of the formulae TI, T2 and T3: in which Q 1 is L, Y and Q are as defined for the compounds of the formula III R 1 and R 2 , in each case independently of one another, are each R, R is alkyl having 1-12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, and Z° is -CH 2 CH 2 - or a single bond, and the 1,4-phenylene rings may also be laterally substituted by fluorine, X is F or OCF 3 , and m is 0 or 1. The proportion of component(s) from group T is preferably 5 % to 30 %, in particular 5 % to 20 %. The proportion of component(s) from group B1 is preferably 5 % to 45 %, in particular preferably about 10 % to 40 %. Components of the formulae B1III and B1IV are preferred. Particularly preferred compounds of the formula B1III are those of the following sub-formulae: in which R 1 is CH 3 -(CH 2 ) n -O-, -CH 3 -(CH 2 ) t -, trans-H-(CH 2 ) r -CH=CH-(CH 2 CH 2 ) s -CH 2 O- or trans-H-(CH 2 ) r -CH=CH-(CH 2 CH 2 ) s -, R 2 is CH 3 -(CH 2 ) t -, n is 1, 2, 3 or 4, r is 0, 1, 2 or 3, s is 0 or 1, and t is 1, 2, 3 or 4. Furthermore preferred compounds are those of the sub-formula in which R 1 and R 2 are as defined above. The proportion of the compounds of the formula B1III of the abovementioned sub-formulae is preferably about 5 % to 45 %, in particular preferably about 10 % to 35 %. Particularly preferred compounds of the formula B1IV are those of the following sub-formula: in which R 1 is CH 3 -(CH 2 ) n -O- or trans-H-(CH 2 ) r -CH=CH-(CH 2 CH 2 ) s -CH 2 O- and R 2 is CH 3 -(CH 2 ) t -, where n is 1, 2, 3 or 4, r is 0, 1, 2 or 3, s is 0 or 1, and t is 1, 2, 3 or 4. The proportion of these compounds or of the compounds of the formula B1IV is preferably about 5 % to 40 %, in particular preferably about 10 % to 35 %. The mixtures preferably contain compounds of the formula III, in particular those of the sub-formula In a particularly preferred embodiment, the mixtures simultaneously contain compounds of the formulae B1III and B1IV, the total proportion for components of group B1 being observed. If compounds of the formulae B1I and B1III are present, R 1 and R 2 are preferably, in each case independently of one another, n-alkyl having 1 to 7 C atoms or (trans)-n-alkenyl having 3 to 7 C atoms. Z 2 is preferably a single bond. BI is particularly preferred. Furthermore preferred mixtures according to the invention are those which contain one or more compounds of the formula B1IV in which and R 1 and R 2 have one of the abovementioned preferred meanings, in particular preferably n-alkyl having 1 to 7 C atoms. In all cases, the total proportion for components of group B1 is observed. The proportion of the compounds of group B2 is preferably about 5 % to 45 %, in particular preferably 5 % to 20 %. The proportion (preferred ranges) for B1V to B1VII is as follows: B1V about 5 % to 30 %, preferably about 5 % to 15 % Total of B1VI and B1VII: about 5 % to 25 %, preferably about 10 % to 20 %. Preferred compounds of group B2 are indicated below: R 1 is preferably n-alkyl having 1 to 7 C atoms or (trans)-n-alkenyl having 3 to 7 C atoms. Z 0 is preferably a single bond. R preferably has the preferred meaning mentioned above for R 1 or is fluorine. Y is preferably fluorine. The mixtures according to the invention preferably contain one or more compounds selected from the group comprising B1V3, B1VI1 and B1VII1 in a total proportion of about 5 to 35 %. In a particularly preferred embodiment, the mixtures according to the invention contain, besides B1V3, B1VI1, B1VII1 and B1V2 (R = F), further terminally fluorinated compounds, for example selected from the group comprising: in which R 1 is preferably n-alkyl having 1 to 7 C atoms or (trans)-n-alkenyl having 3 to 7 C atoms, X is 1 or 2, y is 0 or 1 and Y is H or F. The total proportion of all terminally fluorinated compounds is preferably about 5 % to 65 %, in particular about 15 % to 40 %. The proportion of the compounds from group B3 is preferably about 5 % to 30 %, in particular preferably about 10 % to 20 %. R 1 is preferably n-alkyl or n-alkoxy, each having 1 to 9 C atoms. However, it is also possible to employ analogous compounds containing alkenyl or alkenyloxy groups. Compounds of the formula BVIII are preferred. is preferably 1,4-phenylene. The mixtures according to the invention contain compounds from at least one of groups B1, B2 and B3. They preferably contain one or more compounds from B1 and one or more compounds from group B2 and/or B3. The proportion of compounds of component C is preferably about 5 % to 60 %, in particular about 20 % to 50 %. Those skilled in the art can easily adjust this proportion to produce the threshold voltage desired, it being possible to use, in principle, all customary liquid-crystal compounds where Δε > +2. If predominantly less-positive terminally fluorinated compounds are used, the total proportion can be above the upper range (about 35 % to 80 %), while the proportion may be lower (about 10 % to 35 %) if terminally cyano-substituted compounds are used. In a particularly preferred embodiment, the mixtures according to the invention preferably contain about 5 % to 20 % of one or more compounds having a dielectric anisotropy of less than -2 (component D). Compounds of this type are known, for example derivatives of 2,3-dicyanohydroquinone or cyclohexane derivatives containing the structural element as in DE-OS 3,231,707 or DE-OS 3,407,013. However, compounds containing the structural element 2,3-difluoro-1,4-phenylene are preferably chosen, for example compounds as in DE-OS 3,807,801, 3,807,861, 3,807,863, 3,807,864 or 3,807,908. Particularly preferred are tolans containing these structural elements, as in International Patent Application PCT/DE 88/00133, in particular those of the formulae in which R 1 and R 2 , in each case independently of one another, are preferably n-alkyl having 1 to 7 C atoms or n-alkenyl having 3 to 7 C atoms, and Z 0 is -CH 2 CH 2 - or a single bond. Particularly preferred are also the phenylcyclohexylcarboxylates of the formulae Component D causes, in particular, an improvement in the steepness of the characteristic line. In a particularly preferred embodiment, the mixtures contain about 5 % to 35 %, in particular preferably about 10 % to 20 %, of liquid-crystalline tolan compounds. These make it possible to work with smaller cell thicknesses (about 5-6 µm), which significantly shorten the switching times. Particularly preferred tolans are indicated below: R 1 is preferably n-alkyl having 1 to 7 C atoms, Z 0 is -CH 2 CH 2 - or a single bond, Q is where R 2 is n-alkyl or n-alkoxy, each having 1 to 7 C atoms, or n-alkenyl or n-alkenyloxy, each having 3 to 7 C atoms. In further particularly preferred embodiments, the mixtures contain a component D which contains one or more compounds having a 1-cyano-trans-1,4-cyclohexylene group or a 2,3-difluoro-1,4-phenylene group, at least two compounds of the formulae AIII or AV, compounds of the formulae AIII and AV, at least one compound from the following group: in which alkyl is a straight-chain alkyl group having 2-7 C atoms, and X is H or F, one or more compounds in which R is a trans-alkenyl group or a trans-alkenyloxy group, one or more compounds selected from the following group in which R 1 and R 2 have the preferred meanings indicated in the case of component B, and one of the two 1,4-phenylene groups may also be substituted by fluorine; the proportion of these compounds is 0 % to 25 %, preferably about 5 % to 15 %. In a further particularly preferred embodiment the mixtures contain one or more, in particular 1, 2, 3 or 4, compounds selected from the formulae IIId, IIIb, IIIi and IIIp at least two compounds selected from the formulae AI1, AI3, AI4 or AI5 one or more compounds of the formula B1IV one or more compounds of the formulae T1 or T2 or one or more compounds selected from the following group wherin R1 is defined as for the compounds of the formula III. The construction of the liquid-crystal display elements according to the invention from polarizers, electrode base plates and electrodes having a surface treatment such that the preferential orientation (director) of the liquid-crystal molecules in each case adjacent thereto is usually mutually twisted from one electrode to the other by a value of 160° to 720°, corresponds to the customary construction for display elements of this type. The term customary construction here is used in broad terms and also includes all derivatives and modifications of supertwist cells, in particular also matrix display elements. The surface tilt angle at the two support plates may be identical or different. Identical tilt angles are preferred. An essential difference between the display elements accordding to the invention and the display elements customary hitherto based on the twisted nematic cell is, however, the choice of liquid-crystal components in the liquid-crystal layer. The liquid-crystal mixtures which can be used according to the invention are prepared in a manner customary per se. In general, the desired amount of the components used in a relatively small amount is dissolved in the components making up the principal constituent, expediently at elevated temperature. It is also possible to mix solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, and to remove the solvent again, after mixing, for example by distillation. The dielectrics may also contain further additives known to those skilled in the art and described in the literature. For example, 0-15 % of pleochroic dyes may be added. The examples below are intended to illustrate the invention, without representing a limitation. The abbreviations have the following meanings: S-N smectic-nematic phase transition temperature, N-I nematic-isotrop phase transition temperature, c.p. clear point, visc. viscosity (m Pa.s), T on time from switching on until 90 % of the maximum contrast is reached, T off time from switching off until 10 % of the maximum contrast is reached, V 10 threshold voltage (volt). The SFA is addressed in multiplex operation (multiplex ratio 1:100, bias 1:11, operating voltage 18.5 volts). Above and below, all temperatures are given in °C. Percentages are per cent by weight. The values for the switching times and viscosities relate to 20 °C. In the present patent application and in the following examples all chemical structures of LC compounds are given by acronyms the transformation of which into chemical formulae is done as shown in the following. All residues C n H 2n+1 and C m H 2m+1 are straight-chained alkyl groups with n resp. m carbon atoms. The code of Table B is self-explanatory. In Table A only the acronym for the core structure is given. In a concrete compound this acronym is followed by a dash and a code for the substituents R 1 , R 2 , L 1 and L 2 as follows: Code for R 1 , R 2 , L 1 , L 2 R 1 R 2 L 1 L 2 nm C n H 2n+1 C m H 2m+1 H H nOm C n H 2n+1 OC m H 2m+1 H H nO.m OC n H 2n+1 C m H 2m+1 H H n C n H 2n+1 CN H H nN.F C n H 2n+1 CN H F nF C n H 2n+1 F H H nOF OC n H 2n+1 F H H nCl C n H 2n+1 Cl H H nF.F C n H 2n+1 F H F nOmFF C n H 2n+1 OC m H 2m+1 F F nmF C n H 2n+1 C m H 2m+1 F H nCF 3 C n H 2n+1 CF 3 H H nOCF 3 C n H 2n+1 OCF 3 H H nOCF 2 C n H 2n+1 OCHF 2 H H nS C n H 2n+1 NCS H H rVsN C r H 2r+1 -CH=CH-C s H 2s - CN H H rEsN C r H 2r+1 -O-C s H 2s - CN H H nNF C n H 2n+1 CN F H nAm C n H 2n+1 COOC m H 2m+1 H H nF.Cl C n H 2n+1 Cl H F Cl eu is a mixture consisting of 23.5 % of D-3Cl, 26.3 % of D-5Cl, 27.0 % of CP-3Cl and 23.2 % of CP-5Cl. Cl.F eu is a mixture consisting of 22.50 % of D-3Cl.F 22.50 % of D-5Cl.F 30.25 % of CP-3Cl.F 24.75 % of CP-5Cl.F I eu is a mixture consisting of 33.3 % of I32 33.3 % of I52 33.3 % of I35 The following liquid-crystal mixtures show advantageous properties in SFA. Examples 1a), b) and c) The composition and data for further mixtures are as follows: Example 3 ME2N.F 2.0 ME3N.F 2.0 N - I (°C) + 94 PCH-3 18.0 Δn + 0.1174 PCH-5 11.0 PCH-7 10.0 Visc (cSt) 20 PCH-301 5.0 V 10 2.07 CPTP-303 5.0 CCP-20CF3 9.0 CCP-3OCF3 10.0 CCP-5OCF3 9.0 ECCP-32 5.0 ECCP-33 5.0 ECCP-31 5.0 ECCP-3 4.0 Example 4 PCH-3 18.0 S < -20 N 94 I PCH-5 11.0 V 10 2.07 volt PCH-7 10.0 Δn 0.1174 ME2N.F 2.0 ME3N.F 2.0 CPTP-303 5.0 CCP-2OCF3 9.0 CCP-3OCF3 10.0 CCP-5OCF3 9.0 ECCP-32 5.0 ECCP33 5.0 ECCP31 5.0 ECCP3 4.0 Example 5 K6 7.0 S < -40 N 83 I CCP-2OCF3 8.0 Δn 0.1412 CCP-3OCF3 8.0 CCP-4OCF3 5.0 CCP-5OCF3 6.0 PCH-3 28.0 PCH-4 8.0 PCH-5 13.0 PCH-301 4.0 CPTP-301 5.0 CPTP-302 4.0 CPTP-303 4.0 Example 6 Example 7 N-I + 92° + 90 ° Δn +0.1451 +0.1301 V 10 2.52 1.94 PCH-6F 8.00 PCH-2 9.00 CCP-3OCF3 10.00 PCH-3 22.00 CCP-4OCF3 9.00 PCH-5 12.00 CCP-5OCF3 9.00 PCH-301 13.00 BCH-3F.F 13.00 CCP-3OCF3 7.00 BCH-5F.F 12.00 CCP-5OCF3 7.00 BEP-3F.CL 13.00 ECCP-33 6.00 BEP-5F.Cl 13.00 ECCP-3F 6.00 BCH-52F 13.00 ECCP-3 5.00 CPTP-301 4.00 CPTP-302 4.00 CPTP-303 5.00 Example 8 Example 9 N-I + 78° + 93 ° Δn +0.1263 +0.1340 V 10 2.11 1.93 G9 11.00 K6 6.00 PCH-3 24.00 PCH-2 3.00 PCH-5 5.00 PCH-3 22.00 PCH-301 15.00 PCH-5 11.00 CCP-3OCF3 5.00 PCH-301 6.00 ECCP-3 5.00 CCP-2OCF3 7.00 ECCP-31 5.00 CCP-3OCF3 7.00 ECCP-32 5.00 CCP-4OCF3 7.00 ECCP-33 4.00 CCP-5OCF3 7.00 ECCP-35 4.00 ECCP-3OCF3 6.00 PTP-201 6.00 ECCP-5OCF3 6.00 BCH-32 5.00 CPTP-301 4.00 BCH-52 6.00 CPTP-302 4.00 CPTP-303 4.00 Example 10 Example 11 N-I + 76° + 87 ° Δn +0.1374 +0.1683 V 10 2.02 1.86 G9 10.00 PCH-3 20.00 PCH-3 24.00 K6 7.00 PCH-5 5.00 K9 8.00 CCH-301 10.00 BCH-5 3.00 PCH-301 5.00 PCH-301 6.00 ECCP-3 3.00 PTP-102 8.00 CCP-3OCF3 5.00 PTP-201 8.00 ECCP-3 5.00 CCP-3OCF3 14.00 ECCP-31 5.00 CCP-5OCF3 12.00 ECCP-32 5.00 ECCP-3F 6.00 ECCP-33 4.00 BCH-52F 14.00 PTP-102 7.00 PTP-201 7.00 BCH-32 5.00 BCH-52 5.00 Example 12 Example 13 N-I + 70° + 86 ° Δn +0.1619 +0.1082 V 10 1.76 1.32 PCH-3 20.00 PCH-5F 6.00 K6 9.00 PCH-3 12.00 K9 7.00 ME2N.F 2.00 ME15 9.00 ME3N.F 3.00 PTP-102 8.00 ME5N.F 4.00 PTP-201 8.00 ME7N.F 5.00 CCP-3OCF3 13.00 CCP-2OCF3 7.00 CCP-5OCF3 12.00 CCP-3OCF3 7.00 ECCP-3F 4.00 CCP-4OCF3 6.00 BCH-52F 8.00 CCP-5OCF3 7.00 ECCP-3OCF3 4.00 ECCP-5OCF3 4.00 ECCP-3F.F 6.00 ECCP-5F.F 5.00 ECCP-3 8.00 D-301 4.00 D-302 4.00 D-401 4.00 PTP-201 2.00 Example 14 Example 15 N-I + 77° + 75 ° Δn +0.1265 +0.1274 V 10 2.28 2.01 G9 11.00 PCH-3 10.00 K6 10.00 PCH-4 7.00 PCH-3 19.00 K6 9.00 PCH-301 18.00 K9 9.00 CCP-3OCF3 5.00 PCH-301 5.00 ECCP-3 5.00 CCP-3OCF3 14.00 ECCP-31 5.00 CCP-5OCF3 10.00 ECCP-32 5.00 ECCP-3F 14.00 ECCP-33 5.00 ECCP-32 5.00 ECCP-35 5.00 BCH-32 6.00 BCH-52 6.00 Example 16 Example 17 N-I + 90° + 81 ° Δn - +0.1320 V 10 1.96 1.86 PCH-5F 6.00 K6 3.00 PCH-6F 3.60 PCH-2 4.00 PCH-7F 9.60 PCH-3 28.00 CCP-2OCF3 8.20 PCH-5 13.00 CCP-3OCF3 10.20 PCH-302 12.00 CCP-5OCF3 11.00 CCP-2OCF3 8.00 ECCP-3OCF3 8.30 CCP-3OCF3 8.00 BCH-3F.F 9.50 CCP-4OCF3 6.00 BCH-5F.F 10.30 CCP-5OCF3 6.00 CP-5CL.F 11.80 CPTP-301 4.00 CP-5CL.F 11.80 CPTP-302 4.00 CPTP-303 4.00 Example 18 Example 19 N-I + 73° + 73 ° Δn +0.1712 +0.1694 V 10 1.72 2.02 PCH-3 23.00 K6 8.00 K6 9.00 K9 8.00 K9 7.00 K15 4.00 PTP-4OF 7.00 PCH-3 4.00 PTP-102 8.00 PCH-53 4.00 PTP-201 8.00 PCH-302 10.00 CCP-3OCF3 13.00 PTP-4OF 8.00 CCP-5OCF3 12.00 PTP-102 8.00 ECCP-3F 4.00 PTP-201 8.00 BCH-52F 9.00 ECCP-3F 10.00 CCP-3OCF3 13.00 CCP-5OCF3 10.00 BCH-52F 5.00 Example 20 Example 21 N-I + 82° + 86 ° Δn +0.1198 +0.1221 V 10 2.02 1.96 PCH-3 22.00 PCH-3 22.00 PCH-4 15.00 PCH-4 20.00 PCH-53 5.00 PTP-201 5.00 PTP-201 6.00 CCP-3OCF3 14.00 CCP-3OCF3 14.00 CCP-5OCF3 12.00 CCP-5OCF3 12.00 ECCP-3F 13.00 ECCP-3F 13.00 BCH-52F 14.00 BCH-52F 13.00 Example 22 a) Example 22 b) N-I + 83° + 86 ° Δn +0.1211 +0.1229 V 10 1.94 2.00 PCH-3 22.00 PCH-3 22.00 PCH-4 20.00 PCH-4 20.00 PCH-53 2.00 PTP-201 6.00 PTP-201 5.00 CCP-3OCF3 14.00 CCP-3OCF3 14.00 ECCP-3F 13.00 CCP-5OCF3 12.00 ECCP-5F 12.00 ECCP-3F 12.00 BCH-52F 13.00 BCH-52F 13.00 Example 23 Example 24 N-I + 92° + 84 ° Δn +0.1347 +0.1272 V 10 1.86 1.86 K6 7.00 ME2N.F 2.00 PCH-2 3.00 G9 10.00 PCH-3 22.00 PCH-3 21.00 PCH-5 10.00 PCH-4 12.00 PCH-301 6.00 PCH-5 10.00 CCP-2OCF3 6.00 PCH-301 2.00 CCP-3OCF3 6.00 CPTP-301 4.00 CCP-4OCF3 6.00 CPTP-302 5.00 CCP-5OCF3 6.00 CCP-2OCF3 7.00 ECCP-3OCF3 4.00 CCP-3OCF3 7.00 ECCP-5OCF3 4.00 CCP-4OCF3 7.00 ECCP-3F.F 4.00 CCP-5OCF3 7.00 ECCP-5F.F 4.00 ECCP-33 6.00 CPTP-301 4.00 CPTP302 4.00 CPTP-303 4.00 Example 25 Example 26 N-I + 84° + 86 ° Δn +0.1288 +0.1295 V 10 1.80 1.80 ME2N.F 2.00 ME2N.F 2.00 PCH-3 21.00 PCH-3 21.00 PCH-4 12.00 PCH-4 12.00 PCH-5 20.00 PCH-5 20.00 PCH-301 2.00 PCH-301 4.00 CPTP-301 4.00 CPTP-301 4.00 CPTP-302 5.00 CPTP-302 5.00 CCP-2OCF3 7.00 CCP-2OCF3 7.00 CCP-3OCF3 7.00 CCP-3OCF3 7.00 CCP-4OCF3 7.00 CCP-4OCF3 7.00 CCP-5OCF3 7.00 CCP-5OCF3 7.00 ECCP-33 6.00 ECCP-3 4.00 Example 27 Example 28 N-I + 92° + 78 ° Δn +0.1350 +0.1675 V 10 1.95 2.04 K6 7.00 PCH-5F 9.00 PCH-3 25.00 G9 16.00 PCH-5 10.00 PCH-5 11.00 PCH-301 6.00 K9 6.00 CCP-2OCF3 5.00 K15 6.00 CCP-3OCF3 5.00 PCH-302 8.00 CCP-4OCF3 5.00 PTP-102 5.00 CCP-5OCF3 5.00 PTP-201 6.00 ECCP-3OCF3 4.00 CPTP-301 4.00 ECCP-5OCF3 4.00 CPTP-302 4.00 ECCP-3F.F 6.00 CPTP-303 4.00 ECCP-5F.F 6.00 CCP-3OCF3 7.00 CPTP-301 4.00 BCH-32 7.00 CPTP-302 4.00 BCH-52 7.00 CPTP-303 4.00 Example 29 Example 30 N-I + 87° + 81 ° Δn +0.1262 +0.1267 V 10 1.80 1.88 ME2N.F 2.00 PCH-2 7.00 ME3N.F 2.00 PCH-3 28.00 PCH-3 20.00 PCH-5 13.00 PCH-4 12.00 PCH-302 9.00 PCH-5 18.00 CCH-303 3.00 CPTP-301 4.00 CCP-2OCF3 7.00 CPTP-302 4.00 CCP-3OCF3 7.00 CCP-2OCF3 8.00 CCP-4OCF3 7.00 CCP-3OCF3 8.00 CCP-5OCF3 6.00 CCP-4OCF3 8.00 CPTP-301 4.00 CCP-5OCF3 8.00 CPTP-302 4.00 ECCP-33 6.00 CPTP-303 4.00 Example 31 Example 32 N-I + 81° + 71 ° Δn +0.1527 +0.1695 V 10 1.94 1.75 K6 3.00 PCH-3 16.00 PCH-3 22.00 K6 9.00 PCH-5 15.00 K9 6.00 PCH-301 15.00 K15 6.00 PTP-102 6.00 ME15 8.00 PTP-201 6.00 PTP-102 8.00 CCP-3OCF3 6.00 PTP-201 9.00 CCP-5OCF3 6.00 CCP-3OCF3 13.00 ECCP-3F 6.00 CCP-5OCF3 10.00 ECCP-3 5.00 ECCP-3F 5.00 CPTP-301 3.00 BCH-52F 10.00 CPTP-302 3.00 CPTP-303 4.00 Example 33 Example 34 N-I + 79° + 89 ° Δn +0.1545 +0.1744 V 10 2.50 2.02 PCH-5F 6.00 PCH-3 20.00 PCH-6F 6.00 PCH-5 18.00 PCH-7F 5.00 BCH-5 6.00 CCP-2OCF3 7.00 PTP-4OF 5.00 CCP-3OCF3 10.00 PTP-102 8.00 CCP-5OCF3 10.00 PTP-201 8.00 BCH-3F.F 13.00 ECCP-3F 13.00 BCH-5F.F 13.00 CPTP-301 5.00 PTP-4OF 10.00 BCH-32 2.00 PTP-6OF 8.00 BCH-52F 15.00 PTP-102 5.00 PTP-201 5.00 CPTP-301 2.00 Example 35 Example 36 N-I + 70° + 77 ° Δn +0.1680 +0.1388 V 10 1.91 2.01 PCH-3 24.00 PCH-3 23.00 K6 6.00 PCH-5 14.00 PCH-302 12.00 PCH-301 17.00 PTP-4OF 5.00 CCP-3OCF3 4.00 PTP-102 8.00 ECCP-3 5.00 PTP-201 8.00 ECCP-31 5.00 CCP-3OCF3 10.00 ECCP-32 4.00 BCH-32 10.00 ECCP-33 4.00 BCH-52F 14.00 PTP-102 6.00 PTP-201 6.00 BCH-32 6.00 BCH-52 6.00 Example 37 Example 38 N-I + 78° + 78° Δn +0.1382 +0.1437 V 10 1.38 2.14 ME2N.F 2.00 K9 12.00 ME3N.F 4.00 PCH-5 22.00 ME5N.F 5.00 PCH-5F 8.00 HP-3N.F 3.00 PCH-7F 8.00 HP-4N.F 4.00 CCP-3OCF3 5.00 HP-5N.F 5.00 CCP-5OCF3 5.00 K6 6.00 ECCP-31 5.00 PCH-3 23.00 ECCP-32 5.00 PCH-5 20.00 ECCP-33 5.00 CCP-3OCF3 9.00 ECCP-35 5.00 CCP-4OCF3 8.00 PTP-201 5.00 CCP-5OCF3 9.00 PTP-102 5.00 CPTP-302 2.00 CPTP-302 5.00 BCH-52 5.00 Example 39 Example 40 N-I + 79° + 78 ° Δn +0.1517 +0.1608 V 10 2.12 1.99 K6 6.00 K6 2.00 K9 12.00 K9 12.00 PCH-5 16.00 PCH-5 11.00 PCH-5F 8.00 PCH-5F 8.00 PCH-7F 7.00 PCH-7F 7.00 CCP-3OCF3 5.00 CCP-3OCF3 5.00 CCP-5OCF3 5.00 CCP-5OCF3 5.00 ECCP-31 6.00 ECCP-31 6.00 ECCP-32 5.00 ECCP-32 5.00 ECCP-33 5.00 ECCP-33 5.00 ECCP-35 5.00 PTP-201 5.00 PTP-201 5.00 PTP-102 5.00 PTP-102 5.00 CPTP-302 5.00 CPTP-302 5.00 BCH-32 5.00 BCH-52 5.00 BCH-52 5.00 Example 41 Example 42 N-I + 88° + 70 ° Δn +0.1453 +0.1651 V 10 1.84 1.92 ME2N.F 2.00 PCH-3 14.00 ME3N.F 3.00 K6 7.00 K6 8.00 K9 7.00 PCH-3 21.00 PCH-53 3.00 PCH-5 24.00 PCH-302 11.00 CPTP-301 6.00 PTP-4OF 7.00 CPTP-302 5.00 PTP-102 7.00 CCP-2OCF3 6.00 PTP-201 8.00 CCP-3OCF3 5.00 ECCP-3F 5.00 CCP-4OCF3 6.00 CCP-3OCF3 10.00 CCP-5OCF3 5.00 CCP-5OCF3 8.00 ECCP-31 5.00 BCH-32 5.00 ECCP-32 4.00 BCH-52F 10.00 Example 43 Example 44 N-I + 76° + 73 ° Δn +0.1382 +0.1381 V 10 1.30 - ME2N.F 3.00 PCH-3 23.00 ME3N.F 4.00 G9 14.00 ME5N.F 6.00 PCH-301 17.00 HP-3N.F 3.00 CCP-3OCF3 4.00 HP-4N.F 4.00 ECCP-3 5.00 HP-5N.F 5.00 ECCP-31 5.00 K6 5.00 ECCP-32 4.00 PCH-3 23.00 ECCP-33 4.00 PCH-5 21.00 PTP-102 6.00 CCP-3OCF3 8.00 PTP-201 6.00 CCP-4OCF3 8.00 BCH-32 6.00 CCP-5OCF3 8.00 BCH-52 6.00 CPTP-302 2.00 Example 45 Example 46 N-I + 84° +103 ° Δn +0.1396 +0.1484 V 10 1.64 2.02 K6 7.00 K6 7.00 ME2N.F 3.00 PCH-3 28.00 ME3N.F 3.00 PCH-4 5.00 ME5N.F 3.00 PCH-5 5.00 PCH-3 12.00 PCH-301 4.00 PCH-4 8.00 CCP-2OCF3 8.00 PCH-5 10.00 CCP-3OCF3 8.00 PCH-301 9.00 CCP-4OCF3 5.00 CCP-2OCF3 8.00 CCP-5OCF3 6.00 CCP-3OCF3 8.00 CPTP-301 5.00 CCP-4OCF3 8.00 CPTP-302 6.00 CCP-5OCF3 8.00 CPTP-303 3.00 CPTP-301 5.00 ECCP-3 10.00 CPTP-302 4.00 CPTP-303 4.00 Example 47 Example 48 N-I + 69° + 71 ° Δn +0.1387 +0.1458 V 10 1.68 1.69 PCH-3 22.00 PCH-3 20.00 PCH-4 17.00 PCH-4 10.00 PCH-5 6.0 K6 9.0 K6 9.0 K9 9.0 K9 3.0 K15 12.0 PTP-35 5.0 BCH-5 2.0 CCP-3OCF3 12.0 CCP-3OCF3 14.0 CCP-5OCF3 10.0 CCP-5OCF3 10.0 BCH-32 5.0 ECCP-3F 14.0 BCH-52F 11.0 Example 49 Example 50 N-I + 69° + 71 ° Δn +0.1665 +0.1391 V 10 1.94 1.67 PCH-3 20.00 PCH-3 20.00 PCH-5 4.0 PCH-4 12.0 K6 6.0 K6 9.0 PCH-302 12.0 K9 9.0 PTP-35 9.0 K15 9.0 PTP-102 7.0 CCP-3OCF3 15.0 PTP-201 8.0 CCP-5OCF3 12.0 CCP-3OCF3 8.0 ECCP-3F 14.0 BCH-32 10.0 BCH-52F 16.0 Example 51 Example 52 N-I + 70° + 69 ° Δn +0.1398 +0.1383 V 10 1.74 1.74 K6 7.00 K6 7.00 PCH-3 28.0 PCH-3 25.0 PCH-5 13.0 PCH-5 13.0 PCH-301 11.0 PCH-5F 5.0 CCP-2OCF3 8.0 PCH-301 8.0 CCP-3OCF3 6.0 CCP-2OCF3 8.0 CCP-4OCF3 5.0 CCP-3OCF3 5.0 CCP-5OCF3 4.0 CCP-4OCF3 5.0 ECCP-32 4.0 CCP-5OCF3 4.0 PTP-102 4.0 ECCP-32 5.0 PTP-201 4.0 PTP-102 4.0 CPTP-301 3.0 PTP-201 4.0 CPTP-302 3.0 CPTP-301 3.0 CPTP-302 4.0 Example 53 Example 54 N-I + 72° + 68 ° Δn +0.1431 +0.1418 V 10 1.80 1.85 K6 7.0 PYP-3F 5.0 PCH-3 25.0 PYP-5F 9.0 PCH-5 11.0 PCH-5F 9.0 PCH-5F 10.0 PCH-3 21.0 PCH-301 7.0 PCH-301 12.0 CCP-3OCF3 9.0 CCP-3OCF3 4.0 CCP-5OCF3 8.0 CCP-5OCF3 4.0 ECCP-3 9.0 ECCP-32 4.0 PTP-102 4.0 ECCP-33 4.0 PTP-201 4.0 ECCP-3 8.0 CPTP-301 3.0 PTP-102 4.0 CPTP-302 4.0 PTP-201 4.0 CPTP-301 6.0 CPTP-302 6.0 Example 55 Example 56 N-I + 71° + 84 ° Δn +0.1674 +0.1294 V 10 1.98 1.85 K6 8.0 PCH-2 9.0 K9 9.0 PCH-3 22.0 K12 6.0 PCH-5 14.0 PCH-3 3.0 PCH-301 9.0 PCH-53 4.0 CCP-2OCF3 8.0 PCH-302 10.0 CCP-3OCF3 8.0 PTP-35 8.0 CCP-4OCF3 5.0 PTP-102 7.0 CCP-5OCF3 6.0 PTP-201 7.0 PTP-102 6.0 ECCP-3F 10.0 CPTP-301 5.0 CCP-3OCF3 13.0 CBC-33F 4.0 CCP-5OCF3 10.0 CBC-53F 4.0 BCH-52F 5.0 Example 57 Example 58 N-I + 70° + 72 ° Δn +0.1590 +0.1424 V 10 1.67 1.97 K6 7.0 PYP-3F 5.0 K9 10.0 PYP-5F 8.0 PCH-2 8.0 PCH-5F 9.0 PCH-3 14.0 PCH-3 21.0 PCH-301 13.0 PCH-301 11.0 CCP-2OCF3 8.0 CCP-3OCF3 4.0 CCP-3OCF3 8.0 CCP-5OCF3 5.0 CCP-4OCF3 5.0 ECCP-32 5.0 CCP-5OCF3 6.0 ECCP-33 4.0 PTP-102 6.0 ECCP-3 8.0 PTP-201 6.0 PTP-102 4.0 CPTP-301 5.0 PTP-201 4.0 CPTP-302 4.0 CPTP-301 6.0 CPTP-302 6.0 Example 59 Example 60 N-I + 71° + 76 ° Δn +0.1397 +0.1401 V 10 1.79 1.68 K6 7.0 PCH-3 20.0 PCH-3 23.0 PCH-4 6.0 PCH-5 13.0 K6 9.0 PCH-5F 5.0 K9 9.0 PCH-301 9.0 K15 10.0 CCP-2OCF3 8.0 CCP-3OCF3 15.0 CCP-3OCF3 5.0 CCP-4OCF3 5.0 CCP-4OCF3 5.0 CCP-5OCF3 12.0 CCP-5OCF3 4.0 ECCP-3F 14.0 ECCP-32 5.0 PTP-102 4.0 PTP-201 4.0 CPTP-301 4.0 CPTP-302 4.0 Example 61 Example 62 N-I + 81° + 70 ° Δn +0.1355 +0.1407 V 10 1.82 1.64 PCH-3 22.0 PCH-3 20.0 PCH-4 17.0 PCH-4 16.0 K6 6.0 PCH-5 7.0 PCH-302 7.0 K6 9.0 PTP-201 6.0 K9 9.0 CCP-3OCF3 14.0 BCH-5 3.0 CCP-5OCF3 12.0 PTP-201 3.0 ECCP-3F 10.0 CCP-3OCF3 15.0 CPTP-301 6.0 CCP-5OCF3 12.0 ECCP-3F 6.0 Example 63 Example 64 N-I + 81° + 77 ° Δn +0.1329 +0.1622 V 10 1.93 - PCH-3 22.0 PCH-3 20.0 PCH-4 17.0 PCH-4 6.0 PCH-302 9.0 K6 9.0 PTP-102 5.0 K9 7.0 PTP-201 6.0 PTP-102 8.0 CCP-3OCF3 14.0 PTP-201 8.0 CCP-5OCF3 12.0 CCP-3OCF3 18.0 ECCP-3F 11.0 CCP-5OCF3 14.0 CPTP-301 4.0 BCH-52F 10.0 Example 65 Example 66 N-I + 91° + 87 ° Δn +0.1603 +0.1724 V 10 1.94 1.99 K6 7.0 PCH-5F 4.0 K9 10.0 PCH-3 17.0 PCH-2 9.0 PCH-5 12.0 PCH-3 14.0 K9 6.0 PCH-301 9.0 K15 4.0 CCP-3OCF3 8.0 PCH-302 10.0 CCP-5OCF3 8.0 PTP-102 5.0 ECCP-33 6.0 PTP-201 7.0 ECCP-3F 6.0 CPTP-301 5.0 ECCP-3 5.0 CPTP-302 4.0 PTP-201 5.0 CPTP-303 6.0 CPTP-301 4.0 CCP-3OCF3 7.0 CPTP-302 4.0 CCP-5OCF3 7.0 CPTP-303 5.0 BCH-32 6.0 Example 67 Example 68 N-I + 89° + 81 ° Δn +0.1235 +0.1202 V 10 1.59 2.41 ME2N.F 2.0 PCH-6F 5.0 ME3N.F 3.0 PCH-7F 15.0 PCH-3 12.0 CCP-3OCF3 15.0 PCH-5 8.0 CCP-5OCF3 13.0 PCH-302 14.0 BCH-3F.F 14.0 CCP-3OCF3 12.0 BCH-5F.F 16.0 CCP-5OCF3 11.0 BEP-3CL.F 6.0 BCH-3F.F 12.0 BEP-5CL.F 8.0 BCH-5F.F 10.0 BCH-52F 6.0 BCH-32 6.0 BCH-52 5.0 BCH-52F 5.0 Example 69 Example 70 N-I + 87° + 76 ° Δn +0.1228 +0.1414 V 10 2.59 1.81 PCH-6F 5.0 K6 8.0 PCH-7F 15.0 PCH-3 25.0 CCP-3OCF3 15.0 PCH-5 10.0 CCP-5OCF3 13.0 PCH-301 12.0 BCH-3F.F 14.0 CCP-3OCF3 8.0 BCH-5F.F 16.0 CCP-5OCF3 8.0 PTP-201 7.0 ECCP-3 7.0 BCH-52F 15.0 ECCP-3F 7.0 ECCP-32 3.0 PTP-102 5.0 PTP-201 5.0 CPTP-302 2.0 Example 71 Example 72 N-I + 77° + 73 ° Δn +0.1456 +0.1422 V 10 1.87 1.96 PCH-3 23.0 K6 8.0 PCH-5 13.0 PCH-3 25.0 PTP-4OF 11.0 PCH-5 10.0 PCH-301 9.0 PCH-301 12.0 CCP-2OCF3 7.0 CCP-3OCF3 8.0 CCP-3OCF3 5.0 CCP-5OCF3 8.0 CCP-4OCF3 5.0 ECCP-3 7.0 CCP-5OCF3 5.0 ECCP-31 5.0 ECCP-3 3.0 ECCP-32 5.0 PTP-102 5.0 PTP-102 6.0 PTP-102 4.0 PTP-201 6.0 PTP-201 4.0 CPTP-301 4.0 Example 73 Example 74 N-I + 71° + 72 ° Δn +0.1411 +0.1430 V 10 1.90 1.92 PCH-3 23.0 K6 8.0 PCH-5 14.0 PCH-3 25.0 PTP-4OF 8.0 PCH-5 10.0 PCH-301 11.0 PCH-301 14.0 CCP-2OCF3 7.0 CCP-3OCF3 6.0 CCP-3OCF3 5.0 CCP-5OCF3 6.0 CCP-5OCF3 5.0 ECCP-3 9.0 ECCP-3 5.0 ECCP-31 5.0 ECCP-31 5.0 ECCP-32 5.0 ECCP-32 5.0 PTP-102 6.0 PTP-102 6.0 PTP-201 6.0 PTP-201 6.0 Example 75 Example 76 N-I + 72° + 92 ° Δn +0.1406 +0.1333 V 10 1.96 2.24 PTP-4OF 8.0 PCH-3 20.0 PCH-3 23.0 PCH-5 16.0 PCH-5 14.0 CCP-3OCF3 8.0 PCH-301 13.0 CCP-5OCF3 7.0 CCP-3OCF3 7.0 PCH-301 15.0 CCP-5OCF3 7.0 ECCP-3 10.0 ECCP-3 7.0 ECCP-31 6.0 ECCP-31 5.0 ECCP-32 6.0 ECCP-32 5.0 PTP-102 6.0 PTP-102 5.0 CPTP-302 6.0 PTP-201 6.0 Example 77 Example 78 N-I + 74° + 75 ° Δn +0.1411 +0.1393 V 10 1.95 1.81 K6 7.0 K6 7.0 PCH-3 25.0 PCH-3 25.0 PCH-5 10.0 PCH-5 19.0 PCH-301 13.0 PCH-301 12.0 CCP-3OCF3 8.0 CCP-3OCF3 10.0 ECCP-3 6.0 CCP-5OCF3 11.0 ECCP-31 7.0 ECCP-3 6.0 ECCP-32 6.0 PTP-102 5.0 ECCP-33 6.0 CPTP-302 5.0 PTP-102 6.0 PTP-201 6.0 Example 79 Example 80 N-I + 76° + 76 ° Δn +0.1379 +0.1378 V 10 2.00 1.76 K6 9.0 ME2N.F 2.0 PCH-3 24.0 K6 6.0 PCH-5 10.0 PCH-3 24.0 PCH-301 13.0 PCH-5 19.0 CCP-3OCF3 8.0 PCH-301 12.0 ECCP-3 8.0 CCP-3OCF3 10.0 ECCP-31 5.0 CCP-5OCF3 11.0 ECCP-32 5.0 ECCP-3 7.0 ECCP-33 5.0 PTP-102 4.0 ECCP-35 5.0 CPTP-302 5.0 PTP-102 4.0 PTP-201 4.0 Example 81 Example 82 N-I + 77° + 81 ° Δn +0.1353 +0.1385 V 10 2.01 1.84 K6 8.0 K6 7.0 PCH-3 24.0 PCH-3 28.0 PCH-5 11.0 PCH-5 13.0 PCH-301 13.0 PCH-301 12.0 CCP-3OCF3 8.0 CCP-2OCF3 8.0 ECCP-3 8.0 CCP-3OCF3 8.0 ECCP-31 5.0 CCP-4OCF3 5.0 ECCP-32 5.0 CCP-5OCF3 6.0 ECCP-33 5.0 CPTP-301 5.0 ECCP-35 5.0 CPTP-302 4.0 PTP-102 4.0 CPTP-303 4.0 PTP-201 4.0 Example 83 Example 84 N-I + 77° + 77 ° Δn +0.1322 +0.1281 V 10 1.98 2.05 K6 9.0 K6 9.0 PCH-3 20.0 PCH-3 20.0 PCH-5 14.0 PCH-5 10.0 PCH-301 9.0 PCH-5F 6.0 CCP-3OCF3 9.0 PCH-301 11.0 CCP-5OCF3 9.0 CCP-3OCF3 8.0 ECCP-31 5.0 CCP-5OCF3 8.0 ECCP-32 6.0 ECCP-31 5.0 ECCP-33 6.0 ECCP-32 5.0 ECCP-35 5.0 ECCP-33 6.0 PTP-102 4.0 ECCP-35 5.0 PTP-201 4.0 PTP-102 4.0 CPTP-302 4.0 Example 85 Example 86 N-I + 83° + 84 ° Δn +0.1698 +0.1273 V 10 2.03 2.25 PCH-5F 9.0 PCH-6F 6.0 PCH-3 14.0 PCH-7F 5.0 PCH-5 9.0 PYP-5F 5.0 K9 6.0 CCP-3OCF3 15.0 K15 6.0 CCP-5OCF3 13.0 PCH-302 9.0 ECCP-3F.F 4.0 PTP-102 5.0 BCH-3F.F 18.0 PTP-201 7.0 BCH-5F.F 14.0 CPTP-301 5.0 BEP-3ClF 10.0 CPTP-302 4.0 BEP-5ClF 10.0 CPTP-303 6.0 CCP-3OCF3 7.0 CCP-5OCF3 7.0 BCH-32 6.0 Example 87 Example 88 N-I + 82° + 75 ° Δn +0.1286 +0.1353 V 10 2.22 2.06 PCH-6F 6.0 K6 12.0 PCH-7F 10.0 PCH-3 22.0 CCP-3OCF3 15.0 PCH-5F 10.0 CCP-5OCF3 7.0 PCH-301 5.0 EHP-5F.F 10.0 CCP-3OCF3 7.0 BCH-3F.F 18.0 CCP-5OCF3 6.0 BCH-5F.F 14.0 ECCP-31 6.0 BEP-3ClF 10.0 ECCP-32 6.0 BEP-5ClF 10.0 ECCP-33 6.0 ECCP-35 6.0 PTP-102 6.0 CPTP-302 5.0 Example 89 Example 90 N-I + 76° + 77 ° Δn +0.1371 +0.1371 V 10 1.71 1.64 ME2N.F 2.0 ME2N.F 2.0 ME3N.F 3.0 ME3N.F 3.0 K6 4.0 K6 6.0 PCH-3 24.0 PCH-3 24.0 PCH-5 18.0 PCH-5 16.0 PCH-301 12.0 PCH-301 6.0 CCP-3OCF3 10.0 CCP-3OCF3 11.0 CCP-5OCF3 11.0 CCP-4OCF3 11.0 ECCP-3 7.0 CCP-5OCF3 11.0 PTP-102 4.0 PTP-102 5.0 CPTP-302 5.0 CPTP-302 5.0 Example 91 Example 92 N-I + 80° + 77 ° Δn +0.1689 +0.1368 V 10 1.96 2.03 PCH-5F 9.0 K6 6.0 PCH-3 16.0 K9 6.0 PCH-5 11.0 PCH-3 12.0 K9 6.0 PCH-5 10.0 K15 6.0 PCH-5F 9.0 PCH-302 8.0 PCH-301 8.0 PTP-102 5.0 CCP-3OCF3 7.0 PTP-201 6.0 CCP-5OCF3 6.0 CPTP-301 4.0 ECCP-31 6.0 CPTP-302 4.0 ECCP-32 6.0 CPTP-303 4.0 ECCP-33 6.0 CCP-3OCF3 7.0 ECCP-35 5.0 BCH-32 7.0 PTP-201 4.0 BCH-52 7.0 PTP-102 4.0 CPTP-302 5.0 Example 93 Example 94 N-I + 79° + 75 ° Δn +0.1399 +0.1364 V 10 2.22 1.62 PTP-4OF 6.0 ME2N.F 2.0 K9 6.0 ME3N.F 3.0 PCH-3 12.0 K6 6.0 PCH-5 10.0 PCH-3 24.0 PCH-5F 7.0 PCH-5 16.0 PCH-301 10.0 PCH-301 5.0 CCP-3OCF3 7.0 CCP-2OCF3 8.0 CCP-5OCF3 6.0 CCP-3OCF3 9.0 ECCP-31 6.0 CCP-4OCF3 8.0 ECCP-32 6.0 CCP-5OCF3 9.0 ECCP-33 6.0 PTP-102 5.0 ECCP-35 6.0 CPTP-302 5.0 PTP-201 4.0 PTP-102 4.0 CPTP-302 5.0 Example 95 Example 96 N-I + 93° + 79 ° Δn +0.1412 +0.1343 V 10 1.77 1.94 K6 7.0 PCH-2 8.0 PCH-3 28.0 PCH-3 17.0 PCH-4 8.0 PCH-5 10.0 PCH-5 13.0 PCH-301 11.0 PCH-301 4.0 CCP-20CF3 7.0 CCP-2OCF3 8.0 CCP-3OCF3 7.0 CCP-3OCF3 8.0 CCP-4OCF3 7.0 CCP-4OCF3 5.0 CCP-5OCF3 7.0 CCP-5OCF3 6.0 ECCP-3 5.0 CPTP-301 5.0 ECCP-32 5.0 CPTP-302 4.0 PTP-102 6.0 CPTP-303 4.0 PTP-201 6.0 CPTP-303 4.0 Example 97 Example 98 N-I + 80° +100 ° Δn +0.1606 +0.2005 V 10 1.94 2.91 PCH-2 5.0 PCH-5F 7.0 K6 7.0 PCH-7F 6.0 K9 8.0 BCH-3F.F 14.0 K15 9.0 BCH-5F.F 13.0 PCH-301 15.0 PTP-4OF 10.0 CCP-2OCF3 7.0 PTP-3OF 10.0 CCP-3OCF3 7.0 PTP-102 6.0 CCP-4OCF3 7.0 PTP-201 6.0 CCP-5OCF3 7.0 CPTP-301 5.0 ECCP-3 6.0 CPTP-302 5.0 ECCP-32 5.0 CPTP-303 6.0 PTP-102 6.0 CCP-3OCF3 6.0 PTP-201 6.0 CCP-5OCF3 6.0 CPTP-303 4.0 Example 99 Example 100 N-I + 77° + 78 ° Δn +0.1340 +0.1315 V 10 2.02 2.09 K6 9.0 K6 9.0 PCH-3 22.0 PCH-3 22.0 PCH-5 10.0 PCH-5 10.0 PCH-301 13.0 PCH-301 10.0 CCP-3OCF3 9.0 CCP-3OCF3 9.0 ECCP-3 5.0 ECCP-3F 4.0 ECCP-31 6.0 ECCP-5F 4.0 ECCP-32 6.0 ECCP-31 6.0 ECCP-33 6.0 ECCP-32 6.0 ECCP-35 6.0 ECCP-33 6.0 PTP-102 4.0 ECCP-35 6.0 PTP-201 4.0 PTP-102 4.0 PTP-201 4.0 Example 101 Example 102 N-I + 77° + 76 ° Δn +0.1380 +0.1389 V 10 2.07 1.61 K6 6.0 ME2N.F 2.0 K9 5.0 ME3N.F 4.0 PCH-3 12.0 K6 6.0 PCH-5 12.0 PCH-3 26.0 PCH-5F 8.0 PCH-5 14.0 PCH-6F 4.0 PCH-301 3.0 PCH-301 3.0 CCP-2OCF3 8.0 CCP-3OCF3 7.0 CCP-3OCF3 9.0 CCP-5OCF3 6.0 CCP-4OCF3 9.0 ECCP-31 6.0 CCP-5OCF3 9.0 ECCP-32 6.0 PTP-102 5.0 ECCP-33 6.0 CPTP-302 5.0 ECCP-35 5.0 PTP-201 5.0 PTP-102 4.0 CPTP-302 5.0 Example 103 Example 104 N-I + 76° + 71 ° Δn +0.1378 +0.1401 V 10 1.52 1.70 ME2N.F 2.0 K6 7.0 ME3N.F 4.0 PCH-3 28.0 ME5N.F 5.0 PCH-5 13.0 K6 6.0 PCH-301 11.0 PCH-3 27.0 CCP-2OCF3 8.0 PCH-5 14.0 CCP-3OCF3 8.0 CCP-2OCF3 8.0 CCP-4OCF3 5.0 CCP-3OCF3 9.0 CCP-5OCF3 6.0 CCP-4OCF3 8.0 PTP-102 8.0 CCP-5OCF3 9.0 CPTP-301 6.0 PTP-102 2.0 CPTP-302 6.0 Example 105 Example 106 N-I + 90° + 77 ° Δn +0.1334 +0.1373 V 10 1.88 2.04 PCH-3 22.0 K6 8.0 PCH-4 16.0 PCH-3 22.0 PCH-5 8.0 PCH-5 10.0 HP.3N.F 4.0 PCH-301 13.0 BCH-5 6.0 CCP-3OCF3 8.0 PTP-201 5.0 ECCP-3 6.0 ECCP-3F 12.0 ECCP-31 6.0 ECCP-5F 9.0 ECCP-32 6.0 CCP-3OCF3 8.0 ECCP-33 6.0 BCH-52F 10.0 ECCP-35 5.0 PTP-102 5.0 PTP-201 5.0 Example 107 Example 108 N-I + 75° + 76 ° Δn +0.1366 +0.1358 V 10 1.97 1.56 K6 10.0 ME2N.F 2.0 PCH-3 22.0 ME3N.F 4.0 PCH-5 10.0 K6 5.0 PCH-301 10.0 PCH-3 26.0 CCP-3OCF3 8.0 PCH-5 14.0 ECCP-3F 3.0 PCH-301 4.0 ECCP-5F 3.0 CCP-2OCF3 8.0 ECCP-31 6.0 CCP-3OCF3 9.0 ECCP-32 6.0 CCP-4OCF3 9.0 ECCP-33 6.0 CCP-5OCF3 9.0 ECCP-35 6.0 PTP-102 5.0 PTP-102 5.0 CPTP-302 5.0 PTP-201 5.0 Example 109 Example 110 N-I + 76° + 95 ° Δn +0.1385 +0.1851 V 10 1.49 2.22 ME2N.F 2.0 K9 5.0 ME3N.F 3.0 K12 5.0 ME5N.F 5.0 PCH-3 10.0 K6 6.0 PCH-5 7.0 PCH-3 27.0 PCH-5F 7.0 PCH-5 13.0 PCH-7F 7.0 CCP-2OCF3 9.0 BCH-32 5.0 CCP-3OCF3 9.0 BCH-52 6.0 CCP-4OCF3 8.0 BCH-52F 7.0 CCP-5OCF3 9.0 PTP-102 7.0 PTP-201 3.0 PTP-201 8.0 CPTP-302 6.0 CPTP-301 6.0 CPTP-302 6.0 CPTP-303 6.0 CCP-3OCF3 4.0 CCP-5OCF3 4.0 Example 111 Example 112 N-I + 74 ° + 84 ° Δn +0.1310 +0.1287 V 10 2.12 2.11 G9 5.0 PCH-3 7.0 PCH-3 24.0 PCH-6F 5.0 PCH-5 10.0 PCH-7F 5.0 PCH-301 15.0 CCP-2OCF3 5.0 CCP-3OCF3 8.0 CCP-3OCF3 9.0 ECCP-31 5.0 CCP-4OCF3 5.0 ECCP-32 5.0 CCP-5OCF3 8.0 ECCP-33 4.0 ECCP-3F.F 4.0 ECCP-35 4.0 BCH-3F.F 18.0 PTP-102 5.0 BCH-5F.F 14.0 PTP-201 5.0 BEP-3F.CL 10.0 BCH-32 5.0 BEP-5F.Cl 10.0 BCH-52 5.0 Example 113 Example 114 N-I + 82 ° + 74 ° Δn +0.1510 +0.1363 V 10 1.65 1.97 K6 8.0 G9 10.0 K9 8.0 PCH-3 24.0 PCH-3 20.0 PCH-5 5.0 PCH-4 10.0 PCH-301 13.0 PCH-5 10.0 CCP-3OCF3 10.0 PCH-301 4.0 CCP-5OCF3 5.0 CCP-2OCF3 8.0 ECCP-31 4.0 CCP-3OCF3 8.0 ECCP-32 5.0 CCP-4OCF3 5.0 ECCP-33 4.0 CCP-5OCF3 6.0 PTP-102 6.0 CPTP-301 5.0 PTP-201 6.0 CPTP-302 4.0 BCH-32 6.0 CPTP-303 4.0 BCH-52 6.0 Example 115 Example 116 N-I + 75 ° + 85 ° Δn +0.1432 +0.1341 V 10 1.98 2.24 K6 8.0 K6 10.0 K9 8.0 PCH-3 14.0 PCH-3 16.0 PCH-5 8.0 PCH-5 10.0 PCH-301 10.0 PCH-301 10.0 CCP-3OCF3 10.0 CCP-3OCF3 8.0 CCP-5OCF3 8.0 ECCP-3F 3.0 ECCP-3F 3.0 ECCP-5F 3.0 ECCP-5F 3.0 ECCP-31 6.0 ECCP-31 6.0 ECCP-32 6.0 ECCP-32 6.0 ECCP-33 6.0 ECCP-33 6.0 ECCP-35 6.0 ECCP-35 6.0 PTP-102 5.0 PTP-102 5.0 PTP-201 5.0 PTP-201 5.0 Example 117 Example 118 N-I + 72 ° + 80 ° Δn +0.1357 +0.1424 V 10 2.05 1.98 K6 10.0 K6 10.0 PCH-3 17.0 PCH-3 22.0 G9 15.0 PCH-5 10.0 PCH-301 10.0 PCH-301 10.0 CCP-3OCF3 8.0 CCP-3OCF3 8.0 ECCP-3F 3.0 ECCP-3 10.0 ECCP-5F 3.0 ECCP-3F 3.0 ECCP-31 6.0 ECCP-5F 3.0 ECCP-32 6.0 ECCP-33 7.0 ECCP-33 6.0 ECCP-35 7.0 ECCP-35 6.0 PTP-102 5.0 PTP-102 5.0 PTP-201 5.0 PTP-201 5.0 Example 119 Example 120 N-I + 71° + 99 ° Δn +0.1330 +0.1482 V 10 1.94 1.70 K6 10.0 PCH-3 15.0 PCH-3 22.0 PCH-5F 6.0 PCH-5 10.0 CCP-2OCF3 9.0 PCH-5F 10.0 CCP-3OCF3 10.0 CCP-3OCF3 8.0 CCP-4OCF3 10.0 ECCP-3F 3.0 CCP-5OCF3 10.0 ECCP-5F 3.0 BCH-3F.F 11.0 ECCP-31 6.0 BCH-5F.F 11.0 ECCP-32 6.0 ECCP-3F.F 8.0 ECCP-33 6.0 ECCP-5F.F 8.0 ECCP-35 6.0 CBC-53F 2.0 PTP-102 5.0 PTP-201 5.0 Example 121 Example 122 N-I + 75 ° + 76 ° Δn +0.1365 +0.1351 V 10 2.09 2.19 G9 10.0 G9 10.0 PCH-3 24.0 PCH-3 20.0 PCH-5 5.0 PCH-5 5.0 PCH-301 13.0 PCH-301 15.0 CCP-3OCF3 5.0 CCP-3OCF3 6.0 CCP-5OCF3 4.0 CCP-5OCF3 5.0 ECCP-31 5.0 ECCP-31 5.0 ECCP-32 5.0 ECCP-32 5.0 ECCP-33 5.0 ECCP-33 5.0 PTP-102 6.0 PTP-102 6.0 PTP-201 6.0 PTP-201 6.0 BCH-32 6.0 BCH-32 6.0 BCH-52 6.0 BCH-52 6.0 Example 123 Example 124 N-I + 76 ° + 76 ° Δn +0.1379 +0.1365 V 10 1.52 1.54 ME2N.F 2.0 ME2N.F 2.0 ME3N.F 4.0 ME3N.F 4.0 ME5N.F 5.0 ME5N.F 5.0 K6 5.0 K6 6.0 PCH-3 27.0 PCH-3 27.0 PCH-5 15.0 PCH-5 14.0 CP-3O2FF 5.0 D-302FF 5.0 CCP-2OCF3 6.0 CCP-3OCF3 10.0 CCP-3OCF3 7.0 CCP-4OCF3 9.0 CCP-4OCF3 7.0 CCP-5OCF3 10.0 CCP-5OCF3 9.0 CPTP-301 4.0 PTP-102 4.0 CPTP-302 4.0 CPTP-302 4.0 Example 125 Example 126 N-I + 75 ° + 76 ° Δn +0.1359 +0.1371 V 10 1.60 1.67 HP.3N.F 2.0 ME2N.F 2.0 HP.4N.F 4.0 ME3N.F 4.0 ME2N.F 2.0 K6 5.0 K6 4.0 PCH-3 26.0 PCH-3 27.0 PCH-5 14.0 PCH-4 11.0 PCH-301 7.0 PCH-5 15.0 CP-302FF 5.0 D-3O2FF 7.0 CCP-3OCF3 9.0 CCP-3OCF3 10.0 CCP-4OCF3 9.0 CCP-5OCF3 10.0 CCP-4OCF3 9.0 PTP-102 2.0 PTP-102 6.0 CPTP-302 6.0 CPTP-302 4.0 Example 127 Example 128 N-I + 86 ° + 82 ° Δn +0.1235 +0.1424 V 10 1.92 2.10 PCH-3 22.0 K6 9.0 PCH-4 20.0 PCH-3 24.0 PTP-201 6.0 PCH-5 10.0 CCP-3OCF3 14.0 PCH-301 9.0 CCP-5OCF3 12.0 CCP-3OCF3 8.0 ECCP-3F 13.0 ECCP-3 6.0 BCH-52F 13.0 ECCP-31 5.0 ECCP-32 5.0 ECCP-33 5.0 ECCP-35 3.0 PTP-102 4.0 PTP-201 4.0 BCH-32 4.0 BCH-52 4.0 Example 129 Example 130 N-I + 79 ° + 80 ° Δn +0.1471 +0.1689 V 10 2.15 1.96 K6 6.0 PCH-5F 9.0 K9 6.0 PCH-3 16.0 PCH-3 12.0 PCH-5 11.0 PCH-5 10.0 K9 6.0 PCH-5F 8.0 K15 6.0 PCH-301 7.0 PCH-302 8.0 CCP-3OCF3 7.0 PTP-102 5.0 CCP-5OCF3 6.0 PTP-201 6.0 ECCP-31 6.0 CPTP-301 4.0 ECCP-32 5.0 CPTP-302 4.0 ECCP-33 5.0 CPTP-303 4.0 ECCP-35 5.0 CCP-3OCF3 7.0 PTP-201 5.0 BCH-32 7.0 PTP-102 6.0 BCH-52 7.0 CPTP-302 6.0 Example 131 Example 132 N-I + 82 ° + 81 ° Δn +0.1458 +0.1465 V 10 2.06 2.11 K6 9.0 K6 6.0 PCH-3 24.0 K9 6.0 PCH-5 10.0 PCH-3 12.0 PCH-301 8.0 PCH-5 10.0 CCP-3OCF3 8.0 PCH-5F 7.0 ECCP-3 5.0 PCH-301 7.0 ECCP-31 5.0 CCP-3OCF3 7.0 ECCP-32 5.0 CCP-5OCF3 7.0 ECCP-33 4.0 ECCP-31 6.0 ECCP-35 3.0 ECCP-32 6.0 PTP-102 4.0 ECCP-33 5.0 PTP-201 5.0 ECCP-35 5.0 BCH-32 5.0 PTP-201 5.0 BCH-52 5.0 PTP-102 5.0 CPTP-302 6.0 Example 133 Example 134 N-I + 81 ° + 93 ° Δn +0.1281 +0.1350 V 10 1.88 1.90 PCH-2 7.0 PCH-2 9.0 PCH-3 28.0 PCH-3 22.0 PCH-5 13.0 PCH-5 14.0 PCH-302 12.0 PCH-301 11.0 CCP-2OCF3 8.0 CCP-2OCF3 7.0 CCP-3OCF3 8.0 CCP-3OCF3 7.0 CCP-4OCF3 6.0 CCP-4OCF3 7.0 CCP-5OCF3 6.0 ECCP-3 6.0 CPTP-301 4.0 CPTP-301 4.0 CPTP-302 4.0 CPTP-302 4.0 CPTP-303 4.0 CPTP-303 5.0 CBC-53F 4.0 Example 135 Example 136 N-I + 91 ° + 74 ° Δn +0.1320 +0.1369 V 10 1.86 1.86 PCH-2 9.0 K6 9.0 PCH-3 22.0 PCH-2 12.0 PCH-5 14.0 PCH-3 12.0 PCH-301 11.0 PCH-5 10.0 CCP-2OCF3 7.0 PCH-301 11.0 CCP-3OCF3 7.0 PCH-302 11.0 CCP-4OCF3 7.0 CCP-3OCF3 8.0 CP-302FF 6.0 ECCP-3 8.0 CPTP-301 4.0 ECCP-31 3.0 CPTP-302 4.0 ECCP-32 4.0 CPTP-303 5.0 ECCP-33 4.0 CBC-53F 4.0 CPTP-301 4.0 CPTP-302 4.0 Example 137 Example 138 N-I + 73 ° + 75 ° Δn +0.1352 +0.1394 V 10 1.92 2.10 K6 10.0 G9 10.0 PCH-3 23.0 PCH-3 24.0 PCH-5 10.0 PCH-5 5.0 PCH-301 13.0 PCH-301 15.0 PCH-302 12.0 CCP-3OCF3 5.0 CCP-3OCF3 5.0 ECCP-3 5.0 ECCP-3 8.0 ECCP-31 4.0 ECCP-32 3.0 ECCP-32 4.0 ECCP-33 3.0 ECCP-33 4.0 BCH-32 4.0 PTP-102 6.0 BCH-52 4.0 PTP-201 6.0 CPTP-301 5.0 BCH-32 6.0 BCH-52 6.0 Example 139 Example 140 N-I +104 ° + 93 ° Δn +0.1347 +0.1281 V 10 2.01 1.97 PCH-2 9.0 PCH-2 9.0 PCH-3 22.0 PCH-3 22.0 PCH-5 14.0 PCH-5 14.0 CCH-303 4.0 CCH-303 10.0 CCP-2OCF3 7.0 CCP-2OCF3 7.0 CCP-3OCF3 7.0 CCP-3OCF3 7.0 CCP-4OCF3 7.0 CCP-4OCF3 7.0 CCP-5OCF3 7.0 CCP-5OCF3 7.0 ECCP-3 6.0 CPTP-301 5.0 CPTP-301 4.0 CPTP-302 4.0 CPTP-302 4.0 CPTP-303 5.0 CPTP-303 5.0 CBC-53F 3.0 CBC-53F 4.0 Example 141 Example 142 N-I + 98 ° + 93 ° Δn +0.1263 +0.1274 V 10 2.11 1.86 ME2N.F 2.0 ME2N.F 2.0 ME3N.F 3.0 ME3N.F 3.0 ME5N.F 9.0 ME5N.F 7.0 PCH-301 25.0 ME7N.F 7.0 CCH-303 11.0 PCH-301 22.0 CCP-2OCF3 7.0 CCH-303 11.0 CCP-3OCF3 7.0 CCP-2OCF3 7.0 CCP-4OCF3 7.0 CCP-3OCF3 7.0 CCP-5OCF3 7.0 CCP-4OCF3 7.0 CPTP-301 5.0 CCP-5OCF3 7.0 CPTP-302 5.0 CPTP-301 5.0 CPTP-303 5.0 CPTP-302 5.0 CBC-33F 3.0 CPTP-303 5.0 CBC-53F 4.0 CBC-53F 5.0 Example 143 Example 144 N-I + 76 ° + 87 ° Δn +0.1442 +0.1432 V 10 2.26 3.48 K9 12.0 PCH-3 5.0 G9 22.0 PCH-302 15.0 PCH-5F 7.0 PCH-304 10.0 PCH-7F 7.0 PCH-305 10.0 CCP-3OCF3 6.0 PCH-501 10.0 CCP-5OCF3 6.0 CCP-2OCF3 6.0 ECCP-31 5.0 CCP-3OCF3 6.0 ECCP-32 5.0 CCP-4OCF3 5.0 ECCP-33 5.0 CCP-5OCF3 6.0 ECCP-35 5.0 PTP-102 5.0 PTP-201 5.0 PTP-201 6.0 PTP-102 5.0 CPTP-301 5.0 CPTP-302 5.0 CPTP-302 5.0 BCH-52 5.0 CPTP-303 6.0 Example 145 Example 146 N-I + 75 ° + 85 ° Δn +0.1365 +0.1372 V 10 2.10 1.88 PCH-3 23.0 PCH-3 15.0 G9 20.0 PCH-4 16.0 PCH-301 10.0 PCH-5 17.0 PYP-34 4.0 PCH-53 5.0 CCP-3OCF3 4.0 CCP-2OCF3 7.0 ECCP-3 4.0 CCP-3OCF3 8.0 ECCP-31 6.0 CCP-4OCF3 7.0 ECCP-32 6.0 CCP-5OCF3 8.0 ECCP-33 6.0 PTP-102 3.0 PTP-102 3.0 PTP-201 3.0 PTP-201 3.0 CPTP-301 5.0 CPTP-3OCF3 5.0 CPTP-302 6.0 CPTP-5OCF3 6.0 Example 147 Example 148 N-I + 87 ° + 74 ° Δn +0.1423 +0.1394 V 10 2.34 2.10 PCH-3 17.0 PCH-3 23.0 G9 7.0 G9 14.0 PCH-302 13.0 PCH-301 13.0 PCH-501 6.0 PYP-34 5.0 CCP-2OCF3 8.0 CCP-3OCF3 4.0 CCP-3OCF3 8.0 ECCP-3 3.0 CCP-4OCF3 5.0 ECCP-31 6.0 CCP-5OCF3 6.0 ECCP-32 6.0 PTP-102 5.0 ECCP-33 6.0 PTP-201 8.0 PTP-102 4.0 CPTP-301 3.0 PTP-201 4.0 CPTP-302 3.0 CPTP-3OCF3 6.0 CPTP-303 3.0 CPTP-5OCF3 6.0 ECCP-31 4.0 ECCP-32 4.0 Example 149 Example 150 N-I + 96 ° + 75 ° Δn +0.1301 +0.1355 V 10 1.96 2.09 PCH-2 9.0 G9 10.0 PCH-3 22.0 PCH-3 24.0 PCH-5 14.0 PCH-5 5.0 CCH-303 11.0 PCH-301 10.0 CCP-2OCF3 5.0 CCH-303 3.0 CCP-3OCF3 6.0 CCP-3OCF3 5.0 CCP-4OCF3 5.0 CCP-5OCF3 4.0 CCP-5OCF3 6.0 ECCP-31 5.0 ECCP-3 6.0 ECCP-32 5.0 CPTP-301 4.0 ECCP-33 5.0 CPTP-302 4.0 PTP-102 6.0 CPTP-303 5.0 PTP-201 6.0 CBC-53F 3.0 BCH-32 6.0 BCH-52 6.0 Example 151 Example 152 N-I + 72 ° + 85 ° Δn +0.1375 +0.1394 V 10 2.10 1.42 PCH-3 13.0 ME2N.F 2.0 G9 24.0 ME3N.F 4.0 PCH-301 17.0 ME5N.F 5.0 CCP-3OCF3 4.0 HP-3N.F 3.0 ECCP-3 5.0 HP-4N.F 4.0 ECCP-31 5.0 HP-5N.F 5.0 ECCP-32 4.0 PCH-3 24.0 ECCP-33 4.0 PCH-5 22.0 PTP-102 6.0 CCP-3OCF3 7.0 PTP-201 6.0 CCP-4OCF3 7.0 BCH-32 6.0 CCP-5OCF3 7.0 BCH-52 6.0 CPTP-3OCF3 5.0 CPTP-5OCF3 5.0 Example 153 Example 154 N-I + 75 ° + 92 ° Δn +0.1372 +0.0837 V 10 1.97 1.81 G9 10.0 PCH-5F 6.0 PCH-3 24.0 PCH-6F 6.0 PCH-5 7.0 PCH-7F 3.0 ME15 10.0 CCH-303 3.0 PCH-301 6.0 CCH-302 3.0 CCP-3OCF3 5.0 CCP-2OCF3 9.0 ECCP-3 5.0 CCP-3OCF3 9.0 ECCP-31 5.0 CCP-4OCF3 9.0 ECCP-32 5.0 CCP-5OCF3 9.0 ECCP-33 4.0 ECCP-3F.F 9.0 PTP-102 5.0 ECCP-5F.F 9.0 PTP-201 4.0 ECCP-3OCF3 5.0 BCH-32 5.0 EHP-3F.F 10.0 BCH-52 5.0 EHP-5F.F 10.0 Example 155 N-I + 94 ° Δn +0.1169 V 10 1.97 ME2N.F 2.0 ME3N.F 2.0 ME5N.F 5.0 PCH-3 15.0 PCH-5 10.0 PCH-301 11.0 CPTP-303 5.0 CCP-2OCF3 9.0 CCP-3OCF3 9.0 CCP-5OCF3 9.0 ECCP-31 5.0 ECCP-32 5.0 ECCP-33 5.0 ECCP-35 4.0 ECCP-3 4.0

Claims: Supertwist liquid crystal display having two plane-parallel carrier plates which, with an edging, form a cell, a nematic liquid crystal mixture of positive dielectric anisotropy in the cell, electrode layers with superimposed orientation layers on the inside of the carrier plates, an angle of incidence between the longitudinal axis of the molecules on the surface of the carrier plates and the carrier plates of about 1 degree to 30 degrees and the absolute amount of the twisting angle of the liquid crystal mixture in the cell from orientation layer to orientation layer being between 160 and 720°, characterized in that the nematic liquid crystal mixture contains one or more compounds of the formula I and/or one or more compounds of the formula II and/or one or more compounds of the formula III wherein R 1 is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, r is 0 or 1, s is 0, 1 or 2, rings A 1 and A 2 are independently from each other trans-1,4-cyclohexylene, 1,4-phenylene or 3-fluoro-1,4-phenylene, A 3 denotes Q is OCHF, OCF 2 , CF 2 or a single bond, Y is H, F, or Cl and L denotes H or F and at least one compound of the formula B1VIII: in which R 1 and R 2 in each case independently of one another are alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, and or at least one compound of the formula in which R 1 is CH 3 -(CH 2 ) n -O-, CH 3 -(CH 2 )t-, trans-H-(CH 2 ),-CH=CH-(CH 2 CH 2 ) s -CH 2 -O-, trans-H-(CH 2 ),-CH=CH-(CH 2 -CH 2 ) s - R 2 is CH 3 -(CH 2 ) t -, n is 1, 2, 3 or 4, t is 1, 2, 3 or 4, r is 0, 1, 2, 3, s is 0 or 1. Supertwist liquid crystal display having two plane-parallel carrier plates which, with an edging, form a cell, a nematic liquid crystal mixture of positive dielectric anisotropy in the cell, electrode layers with superimposed orientation layers on the inside of the carrier plates, an angle of incidence between the longitudinal axis of the molecules on the surface of the carrier plates and the carrier plates of about 1 degree to 30 degrees and the absolute amount of the twisting angle of the liquid crystal mixture in the cell from orientation layer to orientation layer being between 160 and 720°, characterized in that the nematic liquid crystal mixture contains one or more compounds of the formula III wherein R 1 is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, A 3 denotes and Q is OCHF, OCF 2 or CF 2 , Y is H, F or Cl and L denotes H or F in combination with one or more compound of formula B1VIII as defined in claim 1 or one or more compound of cyclohexylcyclohexanes as defined in claim 1 Display according to claim 1 or 2, characterized in that the nematic liquid crystal mixture further comprises a) 5-60 % by weight of a liquid crystalline component A consisting of one or more compounds having a dielectric anisotropy of more than +8, b) 10-40 % by weight of a liquid crystalline component B consisting of one or more compounds having a clearing point of more than 120 °C, and c) an optically active component C, in an amount such that the ration between the layer thickness (separation of the plane-parallel carrier plates) and the natural pitch of the chiral nematic liquid crystal mixture is more than 0.2 adjusted to the desired twist angle, and in that the nematic liquid crystal mixture has a nematic phase range of at least 60 °C, a viscosity of not more than 30 mPa.s and a dielectric anisotropy of at least +5, the dielectric anisotropies of the compounds and the parameters relating to the nematic liquid crystal mixture being based on a temperature of 20 °C. Display according to claim 3, characterized in that component A comprises compounds selected from the following group: wherein R is alkyl having 1-12 C atoms, wherein one or two non-adjacent CH 2 groups can also be replaced by -O-, -CH=CH-, -CO-, -O-CO- or -CO-O-, Q is the formula Z 1 is a single bond, -CH 2 CH 2 -, -CO-O-, or -O-CO- and Display according to one of claims 1 to 4, characterized in that component B comprises compounds selected from the following group: wherein R 1 and R 2 each independently of one another are R as defined in claim 4, Z o is -CO-O-, -O-CO- or -CH 2 CH 2 -, Q is as defined in claim 4 and the 1,4-phenylene ring in BI to BVII may also be substituted in 2- or 3-position by fluorine. Display according to one of claims 1 to 5, characterized in that the liquid crystal mixture contains at least one component selected from group T, comprising compounds of the formulae T1, T2 and T3 in which Q 1 is R 1 , L, Y and Q are as defined in claim 1, R is as defined in claim 4 Z o is -CH 2 CH 2 - or a single bond, X is F or OCF 3 , and m is 0 or 1. Display according to at least one of claims 4 to 6, characterized in that the liquid crystal mixture contains one or more compounds wherein R is a trans-alkenyl group or a trans-alkenyloxy group. Liquid crystal mixture characterized in that it contains one or more compounds of formula II as defined in claim 1. Liquid crystal mixture characterized in that it contains one or more compounds of formula III and at least one compound of formula B1VIII as defined in claim 1. Liquid crystal mixture according to claim 1 characterized in that it contains at least one of the compounds of formula wherein R 1 is CH 3 -(CH 2 ) t - R 2 is CH 3 -(CH 2 ) t -, and t is 1, 2, 3 or 4. Liquid crystal mixture according to one of the claims 8 to 10 comprising the composition as defined in at least one of claims 3 to 7.

Inventors: BARTMANN EKKEHARD DR, COATES DAVID DR, HITTICH REINHARD DR, KOBAYASHI KEIKO DR, LYMER KARL PHILIP DR, MARDEN SHIRLEY ANN DR, NUMATA HIROSHI DR, PLACH HERBERT DR, REIFFENRATH VOLKER, WEBER GEORG, YOSHITAKE HIROKI DR, BARTMANN, EKKEHARD, DR., COATES, DAVID, DR., HITTICH, REINHARD, DR., KOBAYASHI, KEIKO, DR., LYMER, KARL PHILIP, DR., MARDEN, SHIRLEY ANN, DR., NUMATA, HIROSHI, DR., PLACH, HERBERT, DR., REIFFENRATH, VOLKER, WEBER, GEORG, YOSHITAKE, HIROKI, DR.
Applicants: MERCK PATENT GMBH
Application year: 1991
Main classification: C09K19
IPC codes: C09K19, G02F1