Silicon compound, liquid cystal composition and liquid crystal display

Information

  • Patent Application
  • 20030168632
  • Publication Number
    20030168632
  • Date Filed
    February 28, 2002
    22 years ago
  • Date Published
    September 11, 2003
    21 years ago
Abstract
Silicon compounds having a low viscosity and a low threshold voltage and improved mutual solubility, a liquid crystal composition comprising the same and a liquid crystal display using the liquid crystal composition. The silicon compound is represented by formula (1): 1
Description


BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention


[0002] The present invention relates to a novel liquid crystalline compound and a liquid crystal composition (hereinafter referred to merely as a composition according to circumstances). More specifically, it relates to a liquid crystalline compound having a SiH3 group at an end, a composition comprising the same and a liquid crystal display constituted using this composition. The term “liquid crystalline compound” used in the present invention is a general term for a compound showing a liquid crystal phase and a compound which does not show a liquid crystal phase but is useful as a component for a liquid crystal composition.


[0003] 2. Description of the Related Art


[0004] A liquid crystal display (LCD) making use of characteristics of a nematic liquid crystal phase is widely used for various uses including monitors for personal computers and portable telephones, and demand therefor has been growing large year by year. In accordance with it, improvement items for performances required for LCD have come to extend over many divergences such as an expansion in an operable temperature range, a shift to a high density and coloring of a display picture plane, an acceleration in response and an expansion in a viewing angle. Various display modes using electro-optical effects, such as a DS (Dynamic Scattering) mode, a TN (Twisted Nematic) mode, a GH (Guest Host) mode, an STN (Super Twisted Nematic) mode, an IPS (In-Plane switching) mode, a VA (Vertical Alignment) mode and OCB (Optically Compensated Bend) have been proposed in order as means for solving them.


[0005] In such situation, various characteristics are required to a composition used for LCD according to the respective display modes. First, the physical property values such as a birefringence (Δn), a dielectric anisotropy (Δε), a viscosity (η), a conductivity and an elastic constant ratio K33/K11 (K33: bend elastic constant and K11: spray elastic constant) of a liquid crystal composition are required to have values which are optimum for a display mode and a form of an element. Further, in order to achieve high-speed response in any of the LCD's shown above, a composition having a low viscosity is required, and a liquid crystalline compound has to be indispensably reduced as well in a viscosity. In addition thereto, given as common items of characteristics required to a composition are stability against moisture, light, heat and air which are usually present under an use environment and stability against an electric field and electromagnetic irradiation. Further, it is important that a liquid crystalline compound constituting a composition is chemically stable under use conditions and that they have a good solubility with each other.


[0006] In the existing state, however, it is very difficult to solve these problems only with the existing liquid crystal compounds and compositions, and it is an urgent matter to develop a novel liquid crystalline compound and composition which can meet the various requirements described above.


[0007] In recent years, development of various techniques in a liquid crystal display has been tried for the purpose of an enlargement in a picture plane. Especially, liquid crystal compositions which contribute largely to a reduction in power consumption and high speed response are desired to be developed. It is essential for a reduction in power consumption to further reduce a threshold voltage of a composition (E. Jakeman et al., Phys. Lett., 39A. 69 (1972)). Also, a low viscosity is important as well for high speed response. Various compounds have so far been developed in order to achieve these objects. For example, compounds having a silyl group in a molecule represented by the following formulas (a), (b) and (c) are known respectively according to Japanese Patent Application Laid-Open No. 9653/1994, Japanese Patent Application Laid-Open No. 2878/1995 and Japanese Patent Application Laid-Open No. 2879/1995:
2


[0008] In these compounds, silicon is substituted with three alkyl groups. For example, the present inventors measured the physical property values of a compound having a propyldimethylsilyl group represented by the following formula (d) to find the problem that it had not only a markedly high viscosity but also an unsatisfactory mutual solubility with other components constituting a composition:
3


[0009] Physical property measurement: a nematic phase-isotropic phase transition temperature (NI) and a viscosity (η) at 20° C. of a liquid crystal composition ZLI-1132 manufactured by Merck Co., Ltd. were 72.6° C. and 26.7 mPa.s respectively. Then, 15% by weight of the compound represented by the formula (d) was added to 85% by weight of this composition, and NI and η of the resulting composition were determined to find that they were 15° C. or lower and 39.7 mPa.s respectively. It has been found from this result that a composition prepared using the compound represented by the formula (d) is not only notably increased in a viscosity but also reduced in NI by 50° C. or lower. Further, the compound represented by the formula (d) was inferior in mutual soluboility with the other compositions.



SUMMARY OF THE INVENTION

[0010] An object of the present invention is to solve problems on conventional techniques and provide a novel silicon compound which has a low viscosity and a low threshold voltage and which is improved in mutual solubility, a composition comprising the same and a liquid crystal display using the above composition.


[0011] In order to achieve the objects described above, the following inventions are claimed for the grant of a patent in the present application.


[0012] [1] A silicon compound represented by formula (1):


H3Si—Y1—A1—Z1—A2&Parenopenst;Z2—A3&Parenclosest;p&Parenopenst;Z3—A4&Parenclosest;qY2  (1)


[0013] wherein Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in this alkylene may be replaced by —O—, —S—, —CO—, —CH═CH— or —C—C—, but —O— and —O—, —S—and —S—, —O— and —S—, —O— and SiH3, or —S— and SiH3 are not adjacent, and at least one hydrogen in the alkylene may be replaced by halogen or —CN; Y2 is hydrogen, halogen, —CN, —C≡—C—CN, or alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —S—,—S—, —CO—, —CH═CH—, or —C≡C—, but —O— and —O—, —S— and —S—, or —O— and —S— are not adjacent, and any hydrogen in the alkyl may be replaced by halogen or —CN; A1, A2, A3, and A4 each are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, or 1,4-phenylene in which any hydrogen is replaced by halogen; in which any hydrogen in 1,4-cyclohexylene or 1,4-cyclohexenylene may be replaced by halogen, any —CH2— in these rings may be replaced by —O—, but —O— and —O— are not adjacent, and any —CH═ in 1,4-phenylene may be replaced by —N═; Z1, Z2 and Z3 each are independently a single bond, —(CH2)2—, —OCH2—, —CH2O—, —CH═CH—, —C≡C—, —(CH2)4—, —O(CH2)3—, —(CH2)3O—, —COO—, —OCO—, —OCF2—, or —CF2O—; and p and q each are independently 0 or 1.


[0014] [2] The silicon compound defined in the above item [1], wherein in formula (1) described above, p and q are 0; A1 and A2 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z1 is a single bond, —(CH2) 2-, —CH═CH—, —C≡C—, —(CH2)4—, —COO—, —OCO—, —OCF2—, or —CF2O—.


[0015] [3] The silicon compound defined in the above item [1], wherein in formula (1) described above, p is 1, and q is 0; A1, A2 and A3 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z1 and Z2 each are independently a single bond, —(CH2)2—, —CH═CH—, —C≡C—, —COO—, —OCO—, —(CH2)4—, —OCF2—, or —CF2O—.


[0016] [4] The silicon compound defined in the above item [1], wherein in formula (1) described above, p and q are 1; A1, A2, A3, and A4 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z1, Z2 and Z3 each are independently a single bond, —(CH2)2—, —CH═CH—, —C≡C—, —COO—, —OCO—, —(CH2)4—, —OCF2—, or —CF2O—.


[0017] [5] The silicon compound defined in the above item [1], wherein in formula (1) described above, Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in this alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH3 are not adjacent; Y2 is alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O—, —CH═CH— or —C≡C—, but —O— and —O— are not adjacent; and A1, A2, A3, and A4 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene, or pirimidine-2,5-diyl.


[0018] [6] The silicon compound defined in the above item [1], wherein in formula (1) described above, Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in the alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH3 are not adjacent; Y2 is halogen, —CN, —C≡C—CN or alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O—, but —O— and —O— are not adjacent, and at least one hydrogen is replaced by halogen; and A1, A2, A3, and A4 each are independently 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by halogen, or pirimidine-2,5-diyl.


[0019] [7] The silicon compound defined in the above item [1], wherein in formula (1) described above, Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in the alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH3 are not adjacent; Y2 is alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O—, —S— or —CH═CH—, but: —O— and —O—, —S— and —S—, or —O— and —S— are not adjacent; A1, A2, A3, and A4 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene in which a 2-position is replaced by halogen, 1,4-phenylene in which a 3-position is replaced by halogen, or 1,4-phenylene in which a 2-position and a 3-position are replaced by halogen, and one of A1, A2, A3, and A4 is always 1,4-phenylene in which a 2-position or a 3-position is replaced by halogen or 1,4-phenylene in which a 2-position and a 3-position are replaced by halogen.


[0020] [8] A liquid crystal composition comprising at least one silicon compound defined in any one of the items [1] to [7].


[0021] [9] The liquid crystal composition defined in the above item [8], comprising at least one silicon compound described in any one of the items [1] to [7] as a first component and at least one compound selected from the group of compounds represented by formulas (2), (3) and (4) as a second component:
4


[0022] wherein R1 is alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O— or —CH═CH—, but —O— and —O— are not adjacent, and any hydrogen in the group may be replaced by fluorine; X1 is fluorine, Chlorine, —OCF3, —OCF2H, —CF3, —CF2H, —CFH2, —OCF2CF2H, or —OCF2CFHCF3; L1 and L2 each are independently hydrogen or fluorine; Z4 and Z5 each are independently —(CH2)2—, —(CH2)4—, —COO—, —CF2O—, —OCF2—, —CH═CH—, or a single bond; a ring B and a ring C each are independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine; and a ring D is 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene in which at least one hydrogen is replaced by fluorine.


[0023] [10] The liquid crystal composition defined in the above item [8], comprising at least one silicon compound described in any one of the items [1] to [7] as the first component and at least one compound selected from the group of compounds represented by formulas (5) and (6) as a second component:
5


[0024] wherein R2 and R3 each are independently alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O— or —CH═CH—, but —O— and —O— are not adjacent, and any X2 hydrogen in the alkyl may be replaced by fluorine; X2 is —CN or —C≡C—CN; a ring E is 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; a ring F is 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which hydrogen is replaced by fluorine, or pyrimidine-2,5-diyl; a ring G is 1,4-cyclohexylene or 1,4-phenylene; Z6 is —(CH2)2—, —COO—, —CF2O—, —OCF2—, or a single bond; L3, L4 and L5 each are independently hydrogen or fluorine; and a, b and c each are independently 0 or 1.


[0025] [11] The liquid crystal composition defined in the above item [8], comprising at least one silicon compound described in any one of the items [1] to [7] as the first component and at least one compound selected from the group of compounds represented by formulas (7), (8) and (9) as a second component:
6


[0026] wherein R4 and R5 each are independently alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O— or —CH═CH—, but —O— and —O— are not adjacent, and any hydrogen in the alkyl may be replaced by fluorine; a ring I and a ring J each are independently 1,4-cyclohexylene or 1,4-phenylene; L6, L7, L8 and L9 each are independently hydrogen or fluorine, and all of them are not hydrogen simultaneously; and Z7 and Z8 each are independently —(CH2)2—, —COO— or a single bond.


[0027] [12] The liquid crystal composition defined in the above item [8], comprising at least one silicon compound described in any of the items [1] to [7] as the first component, at least one compound selected from the group of the compounds represented by formulas (2), (3) and (4) described in the above item [9] as the second component, and at least one compound selected from the group of compounds represented by formulas (10), (11) and (12) as a third component:
7


[0028] wherein R6 and R7 each are independently alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O— or —CH═CH—, but —O— and —O— are not adjacent, and any hydrogen in the alkyl may be replaced by fluorine; a ring K, a ring M and a ring N each are independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, or 1,4-phenylene in which hydrogen is replaced by fluorine; and Z9 and Z10 each are independently —C≡C—, —COO—, —(CH2)2—, —CH═CH— or a single bond.


[0029] [13] The liquid crystal composition defined in the above item [8], comprising at least one silicon compound described in any one of the items [1] to [7] as the first component, at least one compound selected from the group of the compounds represented by formulas (5) and (6) described in the above item [10] as the second component, and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) described in the above item [12] as the third component.


[0030] [14] The liquid crystal composition defined in the above item [8], comprising at least one silicon compound described in any one of the items [1] to [7] as the first component, at least one compound selected from the group of the compounds represented by formulas (7), (8) and (9) described in the above item [11] as the second component and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) described in the above item [12] as the third component.


[0031] [15] The liquid crystal composition defined in the above item [8], comprising at least one silicon compound described in any of the items [1] to [7] as the first component, at least one compound selected from the group of the compounds represented by formulas (2), (3) and (4) described in the above item [9] as the second component, at least one compound selected from the group of the compounds represented by formulas (5) and (6) described in the above item [10] as the third component, and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) described in the above item [12] as a fourth component.


[0032] [16] A liquid crystal composition comprising at least one liquid crystal composition defined in the items [8] and further comprising at least one optically active compound.


[0033] [17] A liquid crystal display using the liquid crystal composition defined in any of the items [8] to [15].


[0034] The compound (1) of the present invention is a compound having a SiH3 group at an end and 2 to 4 six-membered rings (hereinafter referred to as a bicyclic system to a tetracyclic system), and it is physically and chemically very stable under conditions on which a display is used. Further, six-membered rings, a bonding group and side chains constituting the compound (1) having a good mutual solubility, a low viscosity and a low threshold voltage are suitably selected, whereby the desired physical property values can optionally be controlled. The preferred compounds are shown below.
89101112131415161718192021222324252627282930


[0035] Y1 and Y2 mean the same as those described in the item [1] described above.


[0036] Capable of being given as preferred Y1 is alkylene, alkyleneoxy, alkyleneoxyalkylene, alkenylene, alkenyleneoxy, alkenyleneoxyalkylene or alkyleneoxyalkenylene which has 1 to 10 carbon atoms. Among them, the most preferred group includes methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, methyleneoxy, ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy, methyleneoxymethylene, ethyleneoxymethylene, propyleneoxymethylene, methyleneoxyethylene, ethyleneoxyethylene, methyleneoxypropylene, ethyleneoxypropylene, vinylene, 1-propenylene, 2-propenylene, 1-butenylene, 2-butenylene, 3-butenylene, 2-prpenyleneoxy and 2-butenyleneoxy.


[0037] Capable of being given as preferred Y2 is alkyl alkoxy, alkoxyalkyl, alkenyl, alkenyloxy, alkenyloxyalkyl or alkyloxyalkenyl which has 1 to 10 carbon atoms, alkynyl, fluoroalkyl, fluoroalkyloxy, halogen, cyano and cyanoalkynyl. Among them, the particularly preferred groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-propenyloxy, 2-butenyloxy, 2-poentenyloxy, 4-pentenyloxy, 2-propenyloxymethyl, 2-propenyloxyethyl, 3-butenyloxymethyl, 3-methoxy-1-propenyl, 3-methoxy-1-pentenyl, 3-methoxy-2-pentenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, —F, —Cl, —CN, —C≡C—CN, —CF3, —OCF3 and —OCF2H.


[0038] The compound in which one or both of Y1 and Y2 are optically active groups is particularly useful as a chiral dopant. Addition thereof to the composition makes it possible to prevent reverse twist domain from being produced.


[0039] The compound (1) can suitably be used as a component for a composition used for various displays including a TN type, an STN type, a TFT type and so on. Among the compounds (1), the bicyclic and tricyclic compounds show a low viscosity, and the tricyclic and tetracyclic compounds show a high isotropic phase transition temperature.


[0040] The compound (1) having two or more cyclohexane rings in a molecule shows a high isotropic phase transition temperature, a small Δn and a low viscosity. Further, the compound (1) having a dioxane ring or a pyrimidine ring shows a relatively large Δε.


[0041] The compound (1) having at least one benzene ring in a molecule shows a relatively large Δn and a high liquid crystal orientational parameter and therefore is excellent. In particular, the compound (1) having two or more benzene rings in a molecule shows a particularly large Δn, a broad liquid crystal temperature range and a chemically high stability.


[0042] The compound (1) which is substituted with groups such as —F, —CN, —CF3, —OCF3 and —OCF2H so that the dipole moment grows larger in a molecular long axis direction has a large positive Δε, a high isotropic phase transition temperature and a relatively low viscosity. The compound in which these groups are substituted on a benzene ring shows an excellent stability and a particularly large positive Δε. Further, the compound in which plural groups are substituted on a benzene ring shows a larger Δε.


[0043] The compound (1) which is substituted with —F so that the dipole moment grows larger in a molecular short axis direction has a large negative Δε, a high isotropic phase transition temperature and a relatively low viscosity. The compound in which —F is substituted on a lateral side of a benzene ring shows an excellent chemical stability and a large negative Δε. The compound having two or more —F shows a particularly large negative Δε.


[0044] The compound (1) having double bonds on Z1, Z2 or Z3 shows a broad liquid crystal temperature range and a large elastic constant ratio, and therefore it is suitably used as a composition for STN. The compound (1) having a triple bond shows a large Δε.


[0045] These matters make it possible to provide a novel liquid crystalline compound having desired physical properties by suitably selecting rings, side chains and/or bonding groups. Further, the compound (1) in which atoms constituting it are substituted with the isotopes shows the same characteristics and therefore can be used as well.


[0046] The composition of the present invention shall be explained below. This composition preferably contains 0.1 to 99.9% by weight of at least one compound (1) (hereinafter referred to as a first component) in order to allow excellent characteristics to be revealed. The amount is more preferably 1 to 80% by weight and further preferably 1 to 60% by weight.


[0047] The composition may comprise only the first component. It is allowed to be added as the second component, which is at least one compound (hereinafter referred to as a second A component) selected from the compounds (2), (3) and (4) described above or at least one compound (hereinafter referred to as a second B component) selected from the compounds (5) and (6) to the first component. At least one compound selected from the compounds (10), (11) and (12) can also be added as the third component for the purpose of con-trolling a threshold voltage, a liquid crystal phase temperature range, a birefringence, a dielectric anisotropy and a viscosity.


[0048] The compounds which are the respective components for the composition may be the analogues thereof comprising the isotopes of the respective elements since there is no large difference between the physical characteristics thereof.


[0049] In the second A component described above, the suitable examples of the compound (2) are (2-1) to (2-9); the suitable examples of the compound (3) are (3-1) to (3-97); and the suitable examples of the compound (4) are (4-1) to (4-33).
31323334353637383940414243444546


[0050] In the formulas, R1 and X1 mean the same as those described in the item [9] described above.


[0051] These compounds (2), (3) and (4) have a positive dielectric anisotropy and are very excellent in heat stability and chemical stability, so that they are used primarily for a composition for TFT. When preparing a composition for TFT, an amount of the above compound falls in a range of 0.1 to 99.9% by weight, preferably 10 to 97% by weight and more preferably 40 to 95% by weight based on the whole weight of a composition. The compounds (10) to (12) may further be added to the composition for the purpose of controlling a viscosity.


[0052] In the second B component described above, the suitable examples of the compounds (5) to (6) are (5-1) to (5-58) and (6-1) to (6-3) respectively.
474849505152


[0053] In the formulas, R2, R3 and X2 mean the same as those described in the item [10] described above.


[0054] These compounds (5) and (6) have a very large positive dielectric anisotropy, so that they are used mainly for the compositions for STN or TN. These compounds are used particularly for the purpose of reducing a threshold voltage. They are used as well for the purposes of controlling a viscosity and a birefringence and expanding a liquid crystal phase temperature range and also for the purpose of improving steepness. When preparing a composition for STN or TN, a use amount of the compounds (5) and (6) falls in a range of 0.1 to 99.9% by weight, preferably 10 to 97% by weight and more preferably 40 to 95% by weight. A third component described later can further be added for the purpose of controlling a threshold voltage, a liquid crystal phase temperature range, a birefringence, a dielectric anisotropy and a viscosity.


[0055] When preparing a composition having a negative dielectric anisotropy which is suited for a vertical aligning En mode (VA mode), preferably mixed is at least one compound (hereinafter referred to as a second C component) selected from the compounds (7) to (9). The suitable examples of the compounds (7) to (9) in the second C component are (7-1) to (7-3), (8-1) to (8-5) and (9-1) to (9-3) respectively.
5354


[0056] In the formulas, R4 and R5 mean the same as those described in the item [11] described above).


[0057] The compounds (7) to (9) have a negative dielectric anisotropy. The compound (7) having two six-membered rings is used mainly for the purpose of controlling a threshold voltage, a viscosity or a dielectric anisotropy. The compound (8) is used for the purpose of elevating the clearing point to expand a nematic range, reducing a threshold voltage and increasing a dielectric anisotropy.


[0058] The compounds (7) to (9) are used for a composition for a VA mode having a negative value of the dielectric anisotropy. If an amount thereof is increased, a composition is reduced in a threshold voltage but increased in a viscosity. Accordingly, as small amount as possible is preferred as long as a required value of the threshold voltage is satisfied. An amount of the compounds (7) to (9) is preferably 40% by weight or more, more preferably 50 to 90% by weight in the case of uses for a VA mode.


[0059] The compounds (7) to (9) are mixed in a certain case with a composition having a positive dielectric anisotropy for the purpose of controlling an elastic constant and a voltage transmission curve of the composition. An amount thereof is preferably 30% by weight or less.


[0060] In the third component described above, the suitable examples of the compounds (10) to (12) are (10-1) to (10-11), (11-1) to (11-12) and (12-1) to (12-6) respectively.
555657


[0061] In the formulas, R6 and R7 mean the same as those described in the item [12] described above.


[0062] The compounds (10) to (12) have a small absolute value of a dielectric anisotropy and are close to neutrality. The compound (10) is used mainly for the purpose of controlling a viscosity or a dielectric anisotropy. Further, the compounds (11) and (12) are used for the purpose of elevating a clearing point to broaden a nematic range or controlling a dielectric anisotropy. If a use amount of the compounds (10) to (12) is increased, a composition is elevated in a threshold voltage and reduced in a viscosity. Accordingly, they are used preferably in a large amount as long as a required value of the threshold voltage is satisfied. An amount of the compounds (10) to (12) is 40% by weight or less, preferably 35% by weight or less in the case of uses for TFT. An amount in uses for STN or TN is 70% by weight or less, preferably 60% by weight or less.


[0063] A composition of the present invention contains 0.1 to 99% by weight of at least one of the compounds (1), whereby the excellent characteristics are revealed.


[0064] A composition is prepared by a publicly known method, for example, by dissolving various components by heating. Suitable additives are added if necessary, whereby the composition is optimized according to intended uses. Such additives are well known by a person averagely skilled in the art, and described in detail in literatures. A chiral dopant induces a spiral structure of liquid crystal to provide distortion to thereby prevent inverse distortion. The following optically active compounds can be given as the examples of the chiral dopant.
58


[0065] Usually, in the composition of the present invention, these optically active compounds are added to control a pitch in distortion. The pitch in distortion falls preferably in a range of 40 to 200 μm in the case of the compositions for TFT and TN. In the case of the composition for STN, it falls preferably in a range of 6 to 20 μm. Further, in the case of the composition for a bistable TN mode, it falls preferably in a range of 1.5 to 4 μm. Two or more kinds of the optically active compounds may be added for the purpose of controlling a temperature dependency of the pitch.


[0066] The composition of the present invention can also be used as a liquid crystal composition for a G-H mode by adding dichroic dyes such as merocyanines, styryls, azo, azomethines, azoxy, quinophthalones, anthraquinones, tetrazines, or the like. The composition according to the present invention can also be used as a composition for NCAP prepared by micro-capsulizing nematic liquid crystal and Polymer Dispersed Liquid Crystal Display (PDLCD) prepared by forming a three-dimensional network polymer in the liquid crystal, for example, Polymer Network Liquid Crystal Display (PNLCD). It can also be used as a composition for Electrically Controlled Birefringence (ECB) mode and a DS mode The compound (1) is produced by a conventional organic synthetic method. Suitably selected and combined are publicly known and conventional synthetic methods described in publications and magazines such as, for example, Organic Synthesis (John Wiley & Sons), Organic Reactions (John Wiley & Sons), Comprehensive Organic Synthesis (Pergamon Press) and Shin-Zikken Kagaku Koza (Maruzen).


[0067] Suitably selected and combined for introducing an Si part are publicly known and conventional synthetic methods described in publications and magazines such as, for example, Silicon in Organic Synthesis (Butterworths), Silicon Reagents for Organic Synthesis (Springer-Verlag) and Silicon Reagents in Organic Synthesis (Academic Press).


[0068] Routes shown below can be given as the specific examples.
59


[0069] Y1, Y2, A1, A2, A3, A4, Z1, Z2, Z3, p and q each described above are the same as those described in the item [1] described above. Q1 is halogen, and Q2 is halogen or alkoxy. Mt is lithium, potassium, halogenated magnesium or halogenated zinc.


[0070] First, the compound (11) is reacted with metal such as magnesium and various organic metal reagents such as alkyllithium compounds, alkylzinc compounds, alkylpotassium compounds and alkylcadmium compounds, whereby an organic metal reagent (12) is prepared. This is reacted with tretrasubstituted silane such as tetraalkoxysilane and tetrahalosilane to obtain a silicon compound (13). The compound (13) is subjected to reducing treatment with a suitable reducing agent such as lithium aluminum hydride, diisobutylaluminum hydride, sodium borohydride, sodium cyanoborohydride and diborane-THF, whereby it is derived into a compound (1). When other substituents in the compound (13) are reduced with these reducing agents, suitable additives are used or the reaction conditions are controlled to selectively reduce only SiQ23.







EXAMPLES

[0071] The present invention shall be explained below in more details with reference to examples, but the present invention shall not be restricted by these examples. The structures of the compounds were confirmed by means of a nuclear magnetic resonance spectrum and a mass spectrum (hereinafter abbreviated as MS). M+ in MS represents a molecular ion peak. C shows a crystal phase; S shows a smectic phase; N shows a nematic phase; and Iso shows an isotropic liquid phase. A unit of a phase transition temperature is ° C. in all examples.



Example 1

[0072] Production of trans-1-pentyl-4-(trans-4-silylmethylcyclohexyl)cyclohexane (compound (No. 742) in which in Formula (1), Y1 is methylene; Y2 is pentyl; A1 and A2 are trans-1,4-cyclohexylene; Z1 is a single bond; p and q are 0)


[0073] First Step:


[0074] A Grignard reagent was prepared from 100 ml of THF, magnesium (120 mmole) and trans-1-pentyl-4-(trans-4-chloromethylcyclohexyl)cyclohexane (100 mmole) under nitrogen atmosphere. A THF 100 ml solution of tetramethoxysilane (150 mmole) was heated to 65° C., and the Grignard reagent was added dropwise thereto. Further, the solution was stirred at the same temperature for 2 hours, and after left standing for cooling, the reaction mixture was filtered. The solvent was distilled off, and then trans-1-pentyl-4-(trans-4-trimethoxysilylmethyl-cyclohexyl)cyclohexane (65 mmole) was obtained by distillation under reduced pressure.


[0075] Second Step:


[0076] Lithium aluminum hydride (59 mmole) was suspended in 50 ml of THF on an ice bath under nitrogen atmosphere, and a THF 50 ml solution of trans-1-pentyl-4-(trans-4-trimethoxymethylsilylcyclohexyl)cyclohexane (65 mmole), which was obtained in the reaction of the first step, was added dropwise thereto. After stirring for one hour, water was added to the reaction mixture, and insoluble matters were filtered off. The separated organic layer was dried on anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with a silica gel column chromatography (eluent:heptane), and then it was recrystallized from heptane to obtain trans-1-pentyl-4-(trans-4-silylmethylcyclohexyl)cyclohexane (30 mmole). Phase transition temperature: Cr −0.9 S 74.2 Iso


[0077] MS: m/e=280 (M+)



Example 2

[0078] Production of 1-trifluoromethoxy-4-(trans-4-(trans-4-silylethylcyclohexyl)cyclohexyl)benzene (compound (No. 34) in which in Formula (1), Y1 is ethylene; Y2 is —OCF3; A1 and A2 are trans-1,4-cyclohexylene; A3 is 1,4-phenylene; Z1 and Z2 are single bonds; p is 1, and q is 0)


[0079] First Step:


[0080] A Grignard reagent was prepared from 100 ml of THF, magnesium (120 mmole) and 1-trifluoromethoxy-4-(trans-4-(trans-4-chloroethylcyclohexyl)cyclohexyl)benzene (100 mmole) under nitrogen atmosphere. A THF 100 ml solution of tetramethoxysilane (150 mmole) was heated to 65° C., and the Grignard reagent was added dropwise thereto. The solution was stirred at the same temperature for 2 hours, and after left standing for cooling, the reaction mixture was filtered. The solvent was distilled off, and then 1-trifluoromethoxy-4-(trans-4-(trans-4-trimethoxysilylethylcyclohexyl)cyclohexyl)benzene (57 mmole) was obtained by distillation under reduced pressure.


[0081] Second Step:


[0082] Lithium aluminum hydride (51 mmole) was suspended in 50 ml of THF on an ice bath under nitrogen atmosphere, and a THF 50 ml solution of 1-trifluoromethoxy-4-(trans-4-(trans-4-trimethoxysilylethylcyclohexyl)cyclohexyl)-benzene (57 mmole), which was obtained in the reaction of the first step, was added dropwise thereto. After adding dropwise, the solution was stirred for one hour, and water was added to the reaction mixture, followed by filtering off insoluble matters. The separated organic layer was dried on anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with a silica gel column chromatography (eluent: mixed solvent of heptane/toluene), and it was recrystallized from heptane to obtain 1-trifluoromethoxy-4-(trans-4-(trans-4silylethylcyclohexyl)cyclohexyl)benzene (26 mmole).


[0083] MS: m/e=384 (M+)



Example 3

[0084] Production of 1-ethoxy-2,3-difluoro-4-(trans-4-silylbutylcyclohexyl)benzene (compound (No. 676) in which in Formula (1), Y1 is butylene; Y2 is ethoxy; A1 is trans-1,4-cyclohexylene, and A2 is 2,3-difluoro-1,4-phenylene; Z1 is a single bond; p and q are 0)


[0085] First Step:


[0086] A Grignard reagent was prepared from 100 ml of THF, magnesium (120 mmole) and 1-ethoxy-2,3-difluoro-4-(trans-4-chlorobutylcyclohexyl)benzene (100 mmole) under nitrogen atmosphere. A THF 100 ml solution of tetramethoxysilane (150 mmole) was heated to 65° C., and the Grignard reagent was added dropwise thereto. Further, the solution was stirred at the same temperature for 2 hours, and after left standing for cooling, the reaction mixture was filtered. The solvent was distilled off, and then 1-ethoxy-2,3-difluoro-4-(trans-4trimethoxysilyl-butylcyclohexyl)benzene (58 mmole) was obtained by distillation under reduced pressure.


[0087] Second Step:


[0088] Lithium aluminum hydride (52 mmole) was suspended in 50 ml of THF on an ice bath under nitrogen atmosphere, and a THF 50 ml solution of 1-ethoxy-2,3-difluoro-4-(trans-4-trimethoxysilylbutylcyclohexyl)benzene (58 mmole), which was obtained in the reaction of the first step, was added dropwise thereto. After adding dropwise, the solution was stirred for one hour, and water was added to the reaction mixture, followed by filtering off insoluble matters. The separated organic layer was dried on anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with a silica gel column chromatography (eluent: mixed solvent of heptane/toluene), and it was recrystallized from heptane to obtain 1-ethoxy-2,3-difluoro-4-(trans-4-silylbutylcyclohexyl)benzene (25 mmole).


[0089] MS: m/e=326 (M+)



Example 4

[0090] Production of 2-fluoro-1-(4-propylphenyl)-4-(4-silylethylphenyl)benzene (compound (No. 861) in which in Formula (1), Y1 is ethylene; Y2 is propyl; A1 and A3 are 1,4-phenylene; A2 is 2-fluoro-1,4-phenylene; Z1 and Z2 are single bonds; p is 1, and q is 0)


[0091] First Step:


[0092] A Grignard reagent was prepared from 100 ml of THF, magnesium (120 mmole) and 2-fluoro-1-(4-propylphenyl)-4-(4-chloroethylphenyl)benzene (100 mmole) under nitrogen atmosphere. A THF 100 ml solution of tetramethoxysilane (150 mmole) was heated to 65° C., and the Grignard reagent was added dropwise thereto. Further, the solution was stirred at the same temperature for 2 hours, and after left standing for cooling, the reaction mixture was filtered. The solvent was distilled off, and then 2-fluoro-1-(4-propylphenyl)-4-(4-trimethoxysilyl-ethylphenyl)benzene (59 mmole) was obtained by distillation under reduced pressure.


[0093] Second Step:


[0094] Lithium aluminum hydride (53 mmole) was suspended in 50 ml of THF on an ice bath under nitrogen atmosphere, and a THF 50 ml solution of 2-fluoro-(4-propylphenyl)-4-1-(4-trimethoxysilylethylphenyl)benzene (59 mmole), which was obtained in the reaction of the first step, was added dropwise thereto. After adding dropwise, the solution was stirred for one hour, and water was added to the reaction mixture, followed by filtering off insoluble matters. The separated organic layer was dried on anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with a silica gel column chromatography (eluent: heptane), and it was recrystallized from heptane to obtain 2-fluoro-1-(4-propylphenyl)-4-(4-silylethylphenyl)benzene (22 mmole).


[0095] MS: m/e=348 (M+)


[0096] The following compounds were produced according to the methods of Examples 1 to 4.
1Y1A1Z1A2Z2A3Z3A4Y21606162—F2—CH2O—6364—Cl3656667—OCF2H4—C4H86869—OCF35—C3H6O—7071—F6727374—OCF2H7757677—CF38787980—F9818283—OCF310848586—F11878889—CF312909192—OCF313939495—F14969798—OCF2H15—CH2O—99100—F16101102103104—OCF317—CH2O—105106107—OCF2CF318—C3H6O—108109110—CF319111112113114—OCF320115116117118—F21119120121122—OCF222123124125126—CF323127128129130—F24131132133134—OCF325135136137138—F26—C2H4O—139140141—CF2H27142143144145—OCF328146147148149—F29—CH2150151152—OCF2H30153154155156—F31157158159160—F32—CH2O—161162163—Cl33164165166167—OCF334168169170171—OCF335172173174175—F36176177178179—OCF337—C2H4O—180181182—CF338183184185186—OCF339—C3H6187188189—OCF340190191192193—F41—C2H4194195196—OCF2H42197198199200—OCF343201202203204—F44—C3H6205206207—OCF2H45208209210211—OCF2H46212213214215216—OCF2H47217218219220221—F48—CH2O—222223224225—CF349226227228229230—OCF350231232233234235—F51236237238239240—OCF352241242243244245—CF2H53246247248249250—F54—C3H6O—251252253254—OCF355255256257258259—F56260261262263264—OCF357265266267268269—OCF358270271272273274—F59—CH2275276277278—OCF2H60—C2H4O—279280281282—F61283284285286—OCF362287288289290—F63291292293294—OCF364295296297298—F65299300301302—F66303304305306307—OCF367308309310311312—Cl68313314315316317—OCF369—C3H6O—318319320321—F70322323324325326—F71327328329330331—F72332333334335336—OCF373337338339340341—F74—CH2342343344345—OCF2H75—C2H4O—346347348349—F76350351352353354—Cl77355356357358359—OCF378360361362363364—CF2H79—CH2O—365366367368—OCF380369370371372373—F81374375376377378—OCF382—C3H6O—379380381382—OCF2H83383384385386387—F84388389390391392—OCF385393394395396397—F86398399400401402—CF387403404405406407—OCF388408409410411412—F89—CH2413414415416—OCF2H90—C2H4O—417418419420—F91421422423424425—F92426427428429430—OCF393—CH2O—431432433434—CF2H94435436437438439—OCF395440441442443444—F96445446447448449—OCF2H97—C3H6O—450451452453—OCF2H98454455456457458—F99459460461462463—OCF3100464465466467468—F101469470471472473—OCF2H102474475476477478—OCF3103479480481482483—F104—CH2484485486487—CF3105488489490491492—F106493494495496—F107497498499500—Cl108501502503504—OCF3109505506507508—OCF3110509510511512—F111513514515516—OCF3112517518519520—OCF2H113521522523524—F114—CH2O—525526527—OCF3115528529530531—F116—C2H4O—532533534—CF3117—CH2535536537—OCF3118538539540541—F119542543544545—OCF2H120—C3H6O—546547548—F121549550551552553—OCF3122554555556557558—Cl123559560561562563—F124564565566567568—OCF3125569570571572573—F126574575576577578—OCF3127579580581582583—CF2H128584585586587588—F129—CH2O—589590591592—OCF3130593594595596597—F131—C2H4O—598599600601—OCF3132—C2H4602603604605—OCF3133606607608609610—F134611612613614615—OCF2H135—C3H6O—616617618619—F136620621622623624—OCF3137625626627628629—F138630631632633634—OCF3139635636637638639—OCF3140640641642643644—F141645646647648649—OCF3142650651652653654—OCF2H143655656657658659—OCF3144—CH2O—660661662663—F145664665666667668—F146—C2H4O—669670671672—F147—C4H8673674675676—OCF3148677678679680681—F149682683684685686—OCF3150687688689690691—F151692693694695696—OCF3152697698699700701—F153—CH2O—702703704705—CF3154706707708709710—OCF3155711712713714715—F156716717718719720—OCF3157721722723724725—CF3158726727728729730—F159—CH2O—731732733734—OCF3160735736737738739—F161740741742743744—OCF3162745746747748749—OCF3163750751752753754—F164—CH2755756757758—OCF2H165—C2H4O—759760761762—F166763764765766767—OCF3167—CH2O—768769770771—F168772773774775776—CF3169777778779780781—OCF3170782783784785786—F171787788789790791—OCF3172792793794795796—OCF2H173797798799800801—F174802803804805806—OCF3175—C3H6O—807808809810—F176811812813814815—OCF3177816817818819820—OCF3178821822823824825—F179—C2H4O—826827828829—OCF2H180—C4H8830831832833—F181834835836837—OCF3182838839840841—F183842843844845—CF3184846847848849—OCF3185850851852853—F186854855856857—OCF3187858859860861—OCF2H188862863864865—F189—C3H6866867868—F190—CH2O—869870871—OCF3191872873874875—F192—CH2876877878—OCF3193879880881882—F194883884885886—F195887888889890—F196891892893894895—OCF3197896897898899900—F198901902903904905—F199906907908909910—OCF3200911912913914915—F201916917918919920—OCF3202—CH2921922923924—CF2H203925926927928929—F204930931932933934—OCF3205—CH2O—935936937938—OCF3206939940941942943—F207—CH2944945946947—OCF3208948949950951952—F209953954955956957—F210958959960961962—F211963964965966967—OCF3212968969970971972—F213—CH2O—973974975976—CF3214977978979980981—OCF3215982983984985986—F216987988989990991—OCF3217992993994995996—OCF2CFHCF321899799899910001001—F21910021003100410051006—OCF3220—CH21007100810091010—OCF322110111012101310141015—F22210161017101810191020—OCF322310211022102310241025—F224—C3H61026102710281029—OCF322510301031103210331034—F2261035103610371038—F2271039104010411042—Cl2281043104410451046—OCF32291047104810491050—F2301051105210531054—OCF32311055105610571058—OCF2H2321059106010611062—F2331063106410651066—F2341067106810691070—OCF3235—CH2O—107110721073—F2361074107510761077−OCF32371078107910801081—OCF32381082108310841085—F2391086108710881089—OCF32401090109110921093—CF32411094109510961097—F2421098109911001101—F2431102110311041105—OCF32441106110711081109—F2451110111111121113—OCF32461114111511161117—OCF2H2471118111911201121—F2481122112311241125—F2491126112711281129—OCF3250—C3H6O—1130113111321133—F25111341135113611371138—OCF325211391140114111421143—OCF325311441145114611471148—F25411491150115111521153—OCF325511541155115611571158—CF325611591160116111621163—OCF325711641165116611671168—F25811691170117111721173—CF325911741175117611771178—OCF326011791180118111821183—F261—C3H6O—1184118511861187—OCF326211881189119011911192—CF326311931194119511961197—F264—C2H41198119912001201—OCF326512021203120412051206—F26612071208120912101211—OCF326712121213121412151216—OCF326812171218121912201221—F269—CH21222122312241225—OCF2H27012261227122812291230—F27112311232123312341235—OCF327212361237123812391240—F27312411242124312441245—CF327412461247124812491250—OCF327512511252125312541255—F276—C3H6O—1256125712581259—Cl277—C6H121260126112621263—CF3278—C2H41264126512661267—F27912681269127012711272—OCF328012731274127512761277—F28112781279128012811282—OCF32821283128412851286128728312881289129012911292—F284—CH2O—1293129412951296—OCF2H28512971298129913001301—OCF328613021303130413051306—OCF328713071308130913101311—F28813121313131413151316—CF328913171318131913201321—F29013221323132413251326—F29113271328132913301331—OCF329213321333133413351336—CF2H293—C2H41337133813391340—F29413411342134313441345—OCF329513461347134813491350—Cl29613511352135313541355—OCF3297—C3H6O—1356135713581359—F29813601361136213631364—F299—CH2O—1365136613671368—OCF2H30013691370137113721373—OCF330113741375137613771378—OCF330213791380138113821383—F30313841385138613871388—CF330413891390139113921393—OCF330513941395139613971398—F306—C3H6O—1399140014011402—Cl30714031404140514061407—CF2H30814081409141014111412—F30914131414141514161417—OCF331014181419142014211422—F31114231424142514261427—OCF331214281429143014311432—OCF331314331434143514361437—F31414381439144014411442—OCF2H315—CH21443144414451446—F3161447144814491450—F317—CH2O—145114521453—Cl3181454145514561457—OCF33191458145914601461—OCF33201462146314641465—F3211466146714681469—OCF33221470147114721473—CF33231474147514761477—F3241478147914801481—OCF33251482148314841485—F326—C2H4O—148614871488—CFH23271489149014911492—OCF332814931494149514961497—F329—CH21498149915001501—OCF2H33015021503150415051506—OCF333115071508150915101511—F33215121513151415151516—OCF3333—C3H6O—1517151815191520—OCF333415211522152315241525—OCF333515261527152815291530—F33615311532153315341535—F3371536153715381539—CF33381540154115421543—F3391544154515461547—OCF33401548154915501551—F3411552155315541555—OCF33421556155715581559—CF33431560156115621563—F344—CH2156415651566—OCF2H3451567156815691570—F34615711572157315741575—F34715761577157815791580—Cl34815811582158315841585—OCF334915861587158815891590—OCF335015911592159315941595—F35115961597159815991600—OCF335216011602160316041605—CF335316061607160816091610—F354—CH2O—1611161216131614—OCF3355—C2H41615161616171618—F356—C2H4O—1619162016211622—CF335716231624162516261627—OCF335816281629163016311632—F359—CH21633163416351636—CF2H36016371638163916401641—OCF336116421643164416451646—F36216471648164916501651—CFH236316521653165416551656—OCF336416571658165916601661—OCF3365—CH2O—1662166316641665—F36616661667166816691670—OCF2H36716711672167316741675—CF3368—C2H4O—1676167716781679—F36916801681168216831684—OCF337016851686168716881689—F37116901691169216931694—CF337216951696169716981699—OCF337317001701170217031704—F374—CH21705170617071708—CF2H37517091710171117121713—OCF33761714171517161717—F37717181719172017211722—CFH2378—CH2O—1723172417251726—OCF337917271728172917301731—OCF338017321733173417351736—F38117371738173917401741—CF3382174217431744174517461747—CF3383—C5H10O—17481749175017511752—F384175317541755175617571758—OCF3385175917601761176217631764—F386176517661767176817691770—CF3387177117721773177417751776—OCF3388177717781779178017811782—F389—CH217831784178517861787—CF2H390178817891790179117921793—OCF3391179417951796179717981799—F392—C3H618001801180218031804—CFH2393—C2H418051806180718081809—OCF3394181018111812181318141815—F395181618171818181918201821—OCF3396—CH2O—18221823182418251826—OCF2H397—C2H4O—18271828182918301831—CF3398183218331834183518361837—F399183818391840184118421843—OCF3400184418451846184718481849—F401185018511852185318541855—CF3402185618571858185918601861—OCF3403186218631864186518661867—F404—CH218681869187018711872—CF2H405187318741875187618771878—OCF3406—C2H418791880188118821883—F407—CH2O—18841885188618871888—CF2H408188918901891189218931894—OCF3409—C2H418951896189718981899—F410190019011902190319041905—OCF3411—C3H6O—19061907190819091910—OCFH2412191119121913191419151916—CF3413191719181919192019211922—F414192319241925192619271928—OCF3415192919301931193219331934—F416193519361937193819391940—CF3417194119421943194419451946—OCF3418194719481949195019511952—F419—CH219531954195519561957—CF2H420195819591960196119621963—OCF3421196419651966196719681969—F422197019711972197319741975—OCF3423—CH2O—19761977197819791980—OCF2H424198119821983198419851986—CF3425198719881989199019911992—F426—C2H4O—19931994199519961997—OCF3427199819992000200120022003—F428200420052006200720082009—CF3429201020112012201320142015—OCF3430201620172018201920202021—F431—CH220222023202420252026—CF2H432202720282029203020312032—OCF3433203320342035203620372038—F434—C3H620392040204120422043—CFH2435—C2H420442045204620472048—OCF3436204920502051205220532054—F437205520562057205820592060—OCF3438206120622063206420652066—CF2H439—C2H4O—20672068206920702071—CF3440207220732074207520762077—F441—CH220782079208020812082—OCF3442208320842085208620872088—F443208920902091209220932094—CF3444209520962097209820992100—OCF3445210121022103210421052106—F446210721082109211021112112—OCF2H447211321142115211621172118—OCF3448—CH2O—21192120212121222123—F449—C3H621242125212621272128—OCFH2450—C2H421292130213121322133—OCF3451—C4H821342135—CN452—C3H6O—21362137—CN453213821392140—CN454—C4H821412142—CN455—C5H10O—21432144—CN456214521462147—CN457—C4H8214821492150458215121522153—CN459215421552156—CN460215721582159—CN461—C2H4O—2160216121624622163216421652166—CN463—CH2O—216721682169—CN4642170217121722173—CN4652174217521762177—CN466—C4H821782179—CN467—C3H6O—21802181—CN468218221832184—CN469—C4H8218521862187470218821892190—CN471—C2H4O—21912192—CN472219321942195—CN4732196219721982199474220022012202—CN475—CH2O—22032204—CN476220522062207—CN4772208220922102211478—C4H822122213—CN479—C5H10O—22142215—CN4802216221722182219


[0097]

2























Y1
A1
Z1
A2
Z2
A3
Z3
A4
Y2





































481
—C2H4


2220







2221







2222








—CN





482
—C3H6O—


2223







2224







2225









—CN





483


2226







2227







2228







2229









—CN





484
—C2H4


2230







2231







2232











2233










485


2234







2235







2236







2237









—CN





486
—C2H4O—


2238







2239







2240









—CN





487


2241







2242







2243







2244









—CN





488


2245







2246







2247







2248











2249










489
—C3H6


2250







2251







2252









—CN





490
—C3H6


2253







2254







2255









—CN





491


2256







2257







2258







2259









—CN





492


2260







2261







2262







2263









—CN





493
—CH2O—


2264







2265







2266









—CN





494


2267







2268







2269







2270









—CN





495


2271







2272







2273







2274











2275










496
—C2H4


2276







2277







2278









—CN





497
—C3H6O—


2279







2280







2281









—CN





498


2282







2283







2284







2285











2286










499


2287







2288







2289







2290









—CN





500
—C2H4O—


2291







2292







2293









—CN





501


2294







2295







2296







2297









—CN





502


2298







2299







2300







2301









—CN





503
—C3H6O—


2302







2303







2304









—CN





504
—C3H6


2305







2306







2307











2308










505


2309







2310







2311







2312









—CN





506


2313







2314







2315







2316









—CN





507


2317







2318







2319







2320











2321










508
—CH2O—


2322







2323







2324









—CN





509


2325







2326







2327







2328









—CN





510


2329







2330







2331







2332









—CN





511
—C2H4


2333







2334







2335









—CN





512
—C3H6O—


2336







2337







2338









—CN





513


2339







2340







2341







2342









—CN





514
—C2H4O—


2343







2344







2345









—CN





515


2346







2347







2348







2349











2350










516


2351







2352







2353







2354









—CN





517


2355







2356







2357







2358









—CN





518
—C3H6O—


2359







2360







2361









—CN





519
—C3H6


2362







2363







2364









—CN





520


2365







2366







2367







2368











2369










521


2370







2371







2372







2373









—CN





522
—CH2O—


2374







2375







2376









—CN





523


2377







2378







2379







2380











2381










524


2382







2383







2384







2385









—CN





525
—C3H6O—


2386







2387







2388









—CN





526


2389







2390








2391








2392







—CN





527
—CH2O—


2393








2394








2395







—CN





528


2396







2397








2398








2399









2400










529


2401







2402








2403








2404







—CN





530
—C2H4O—


2405








2406








2407







—CN





531


2408







2409








2410








2411









2412










532


2413







2414








2415








2416







—CN





533
—C3H6O—


2417








2418








2419







—CN





534


2420







2421








2422








2423







—CN





535


2424







2425








2426








2427







—CN





536
—C2H4O—


2428








2429








2430







—CN





537
—CH2


2431








2432








2433









2434










538


2435







2436








2437








2438







—CN





539
—CH2O—


2439








2440








2441







—CN





540


2442







2443








2444








2445









2446










541
—C2H4


2447








2448








2449







—CN





542
—C3H6O—


2450








2451








2452







—CN





543


2453







2454








2455








2456









2457










544
—C4H8


2458








2459








2460







—CN





545
—C2H4O—


2461








2462








2463







—CN





546
—C3H6


2464








2465








2466









2467










547


2468







2469








2470








2471







—CN





548
—C3H6O—


2472








2473








2474







—CN





549


2475







2476








2477








2478









2479










550


2480







2481








2482







2483







2484







—CN





551
—C2H4O—


2485








2486







2487







2488







—CN





552
—CH2


2489








2490







2491







2492









2493










553


2494







2495








2496







2497







2498







—CN





554
—CH2O—


2499








2500







2501







2502







—CN





555


2503







2504








2505







2506







2507









2508










556
—C2H4


2509








2510







2511







2512







—CN





557
—CH2O—


2513








2514







2515







2516







—CN





558


2517







2518








2519







2520







2521









2522










559
—C7H14


2523








2524








2525







—CN





560
—C3H6O—


2526








2527








2528







—CN





561
—C3H6


2529








2530








2531









2532










562


2533







2534








2535








2536







—CN





563
—C2H4O—


2537








2538








2539







—CN





564


2540







2541








2542








2543









2544










565


2545







2546








2547








2548







—CN





566
—C2H4O—


2549








2550








2551







—CN





567
—C2H4


2552








2553








2554









2555










568


2556







2557







2558







2559








2560







—CN





569


2561







2562







2563







2564








2565







—CN





570
—CH2O—


2566







2567







2568








2569









2570










571
—C2H4


2571







2572







2573








2574







—CN





572
—CH2O—


2575







2576







2577








2578







—CN





573


2579







2580







2581







2582








2583









2584










574
—C2H4


2585







2586







2587








2588







—CN





575
—C3H6O—


2589







2590







2591








2592







—CN





576
—C3H6


2593







2594







2595








2596







—CN





577


2597







2598








2599







2600







2601







—CN





578
—C3H6O—


2602








2603







2604







2605







—CN





579


2606







2607








2608







2609







2610









2611










580


2612







2613








2614







2615







2616







—CN





581
—C2H4O—


2617








2618







2619







2620







—CN





582
—C2H4


2621








2622







2623







2624









2625










583


2626







2627








2628







2629







2630







—CN





584


2631







2632








2633







2634







2635







—CN





585
—CH2O—


2636








2637







2638







2639









2640










586
—C2H4


2641








2642







2643







2644







—CN





587
—C2H4O—


2645








2646







2647







2648







—CN





588


2649







2650








2651







2652







2653









2654










589
—C4H8


2655








2656







2657







2658







—CN





590
—C3H6O—


2659








2660







2661







2662







—CN





591
—C2H4


2663








2664







2665







2666









2667










592


2668







2669








2670







2671







2672







—CN





593
—C3H6O—


2673








2674







2675







2676







—CN





594


2677







2678








2679







2680







2681







—CN





595


2682







2683








2684







2685







2686







—CN





596


2687







2688








2689







2690







2691







—CN





597
—CH2O—


2692








2693







2694







2695









2696










598


2697







2698








2699







2700







2701







—CN





599
—C2H4O—


2702








2703







2704







2705







—CN





600


2706







2707








2708







2709







2710









2711










601
—C2H4


2712








2713







2714







2715







—CN





602
—C3H6O—


2716








2717







2718







2719







—CN





603


2720







2721








2722







2723







2724









2725










604
—C4H8


2726








2727







2728







2729







—CN





605
—C2H4O—


2730








2731







2732







2733







—CN





606
—C2H4


2734








2735







2736







2737









2738










607


2739







2740








2741







2742







2743







—CN





608
—C3H6O—


2744








2745







2746







2747







—CN





609


2748







2749








2750







2751







2752









2753










610


2754







2755








2756







2757







2758







—CN





611


2759







2760








2761







2762







2763







—CN





612
—C2H4


2764








2765







2766







2767









2768










613


2769







2770








2771







2772







2773







—CN





614
—C2H4O—


2774








2775







2776







2777







—CN





615


2778







2779








2780







2781







2782









2783










616
—C4H8


2784








2785







2786







2787







—CN





617
—C4H8


2788








2789







2790







2791







—CN





618


2792







2793








2794







2795







2796









2797










619
—C2H4


2798








2799







2800







2801







—CN





620
—C2H4O—


2802








2803







2804







2805







—CN





621
—C4H8


2806








2807







2808







2809









2810










622


2811







2812








2813







2814







2815







—CN





623
—C2H4O—


2816








2817







2818







2819







—CN





624
—CH2O—


2820








2821







2822







2823









2824










625


2825







2826








2827







2828







2829








2830





—CN





626
—CH2O—


2831








2832







2833







2834








2835





—CN





627
—C2H4


2836








2837







2838







2839








2840







2841










628


2842







2843








2844







2845







2846








2847





—CN





629
—C2H4O—


2848








2849







2850







2851








2852





—CN





630


2853







2854








2855







2856







2857








2858







2859










631
—C4H8


2860







2861







2862









—F





632


2863







2864







2865







2866









—OCF3





633
—C4H8


2867







2868







2869









—CF3





634
—CH2O—


2870







2871







2872









—OCF2H





635
—C2H4


2873







2874







2875









—CN





636
—C4H8


2876







2877







2878











2879










637
—C4H8


2880







2881







2882









—F





638
—C2H4O—


2883







2884







2885









—F





639


2886







2887







2888







2889









—OCF3





640


2890







2891







2892







2893









—CF2H





641
—C2H4


2894







2895







2896









—CN





642
—C2H4


2897







2898







2899











2900










643


2901







2902







2903







2904









—F





644


2905







2906







2907







2908









—OCF3





645


2909







2910







2911







2912









—OCF3





646
—C4H8


2913







2914







2915









—CF3





647


2916







2917







2918







2919









—CN





648
—C3H6O—


2920







2921







2922











2923










649
—CH2O—


2924








2925







2926







2927







—CN





650
—C2H4


2928








2929







2930







2931







—CN





651
—C4H8


2932








2933







2934







2935









2936










652
—C2H4


2937








2938







2939







2940







—CN





653
—C2H4O—


2941








2942







2943







2944







—CN





654


2945







2946








2947







2948







2949









2950










655


2951







2952








2953







2954







2955







—CN





656
—C4H8O—


2956








2957







2958







2959







—CN





657
—C2H4


2960








2961







2962







2963









2964










658


2965







2966








2967








2968







2969







2970





—CN





659


2971







2972








2973








2974







2975







2976





—CN





660
—C2H4


2977








2978








2979







2980







2981







2982










661
—C4H8


2983








2984








2985







2986







2987





—CN





662


2988







2989








2990








2991







2992







2993





—CN





663
—C2H4


2994








2995








2996







2997







2998





—CN





664
—CH2O—


2999








3000








3001







3002







3003





—CN





665
—C4H8


3004








3005








3006







3007







3008







3009










666
—C2H4


3010








3011








3012







3013







3014





—CN





667
—C2H4


3015








3016









—F





668
—C6H12 O—


3017








3018









—F





669


3019







3020








3021









—F





670


3022







3023








3024









—F





671
—C5H10O—


3025








3026









—F





672


3027







3028








3029









—F





673


3030







3031








3032








3033







—F





674


3034







3035








3036








3037







—F





675


3038







3039








3040








3041







—F





676


3042







3043








3044









—OC2H5





677
—C3H6


3045








3046









—CH3





678


3047







3048








3049









—OC2H5





679
—C4H8O—


3050








3051









—C3H7





680


3052







3053








3054









—OC3H7





681
—C4H8


3055








3056









—OC2H5





682
—C3H6O—


3057








3058









—C2H5





683
—C7H14


3059








3060









—SCH3





684


3061







3062








3063









—OC2H5





685


3064







3065








3066









—C49





686


3067







3068







3069







3070









—OC2H5





687


3071







3072







3073







3074









—C3H7





688
—CH2O—


3075







3076







3077









—OC3H7





689


3078







3079







3080







3081









—OCH3





690


3082







3083







3084







3085









—C5H11





691


3086







3087








3088








3089







—OC2H5





692
—C2H4


3090








3091








3092







—CH3





693
—C4H8


3093








3094








3095







—OC2H5





694


3096







3097








3098








3099







—C2H5





695


3100







3101








3102








3103







—OC3H7





696
—C4H8


3104








3105







3106







3107







—OC2H5





697
—C3H6O—


3108








3109







3110







3111







—C2H5





698
—C7H14


3112








3113







3114







3115







—OCH3





699
—C2H4


3116








3117







3118







3119







—OC2H5





700


3120







3121








3122







3123







3124







—C4H9





701


3125







3126








3127







3128







3129







—OC2H5





702


3130







3131








3132







3133







3134







—C3H7





703
—CH2O—


3135








3136







3137







3138







—OC3H7





704


3139







3140








3141







3142







3143







—OCH3





705


3144







3145








3146







3147







3148







—C5H11





706


3149







3150








3151








3152







—OC2H5





707
—C2H4


3153








3154








3155







—C3H7





708


3156







3157








3158








3159







—OCH3





709
—C3H6O—


3160








3161








3162







—C6H13





710


3163







3164








3165








3166







—OC2H5





711
—C2H4


3167








3168







3169







3170







—OC2H5





712
—CH2O—


3171








3172







3173







3174







—CH3





713
—C4H8


3175








3176







3177







3178







—OCH3





714


3179







3180








3181







3182







3183







—SC2H5





715


3184







3185








3186







3187







3188







—C4H9





716


3189







3190








3191







3192







3193







—OC2H5





717


3194







3195








3196







3197







3198







—C3H7





718
—C2H4


3199








3200








3201







—OC2H5





719


3202







3203








3204








3205







—C3H7





720


3206







3207








3208








3209







—OC2H5





721


3210







3211








3212








3213







—OC2H5





722
—C2H8


3214








3215








3216







—CH3





723


3217







3218








3219








3220







—OC3H7





724
—C3H6O—


3221








3222








3223







—C6H13





725


3224







3225








3226








3227







—OC2H5





726
—C2H4


3228








3229








3230







—OC2H5





727
—CH2O—


3231








3232








3233







—SCH3





728
—C4H8


3234








3235








3236







—C2H5





729


3237







3238








3239








3240







—OC2H5





730


3241







3242








3243








3244







—CH3





731


3245







3246








3247







3248







3249







—OC2H5





732


3250







3251








3252







3253







3254







—CH3





733
—C7H14


3255








3256







3257







3258







—OC2H5





734
—C3H6O—


3259








3260







3261







3262







—C3H7





735


3263







3264








3265







3266







3267







—OC2H5





736


3268







3269








3270









—C4H9





737
—CH2O—


3271








3272









—C7H15





738


3273







3274








3275











3276










739


3277







3278








3279











3280










740


3281







3282








3283









—C5H11





741
—C7H14O—


3284








3285









—OC8H17





742
—CH2


3286








3287









—C5H11





743


3288







3289








3290









—COOCH3





744
—C2H4O—


3291








3292









—COOC2H5





745


3293







3294








3295









—COOC3H7





746


3296







3297







3298







3299









—C5H11





747


3300







3301







3302







3303









—OC4H9





748


3304







3305







3306







3307











3308










749


3309







3310







3311







3312









—C2H5





750


3313







3314







3315







3316











3317










751
—C3H6


3318







3319







3320









—C2H5





752
—CH2O—


3321







3322







3323









—C8H17





753


3324







3325







3326







3327











3328










754


3329







3330







3331







3332











3333










755


3334







3335







3336







3337









—C3H7





756


3338







3339








3340









—C3H7





757
—C2H4O—


3341








3342









—C4H9





758


3343







3344








3345











3346










759


3347







3348








3349









—OC5H11





760


3350







3351








3352











3353










761


3354







3355








3356









—C5H11





762
—C6H12


3357








3358









—CH2OCH3





763


3359







3360








3361









—C2H5





764


3362







3363








3364











3365










765


3366







3367








3368









—OC2H5





766


3369







3370








3371









—OC6H13





767


3372







3373








3374









—C8H17





768


3375







3376








3377











3378










769


3379







3380







3381







3382









—C3H7





770
—C2H4O—


3383







3384







3385









—C4H9





771


3386







3387







3388







3389









—C5H11





772


3390







3391







3392







3393









—OC7H15





773


3394







3395







3396







3397











3398










774


3399







3400







3401







3402











3403










775


3404







3405







3406







3407









—C5H11





776
—C4H8O—


3408







3409







3410









—C2H5





777


3411







3412







3413







3414









—C4H9





778
—CH2


3415







3416







3417









—C2H4OCH3





779


3418







3419







3420







3421











3422










780


3423







3424







3425







3426











3427










781


3428







3429







3430







3431









—C3H7





782
—C2H4O—


3432







3433







3434









—C6H13





783


3435







3436







3437







3438









—OC7H15





784


3439







3440







3441







3442











3443










785


3444







3445







3446







3447









—C3H7





786


3448







3449







3450







3451









—C3H7





787
—CH2


3452







3453







3454









—OC5H11





788
—C2H4O—


3455







3456







3457









—C6H13





789


3458







3459







3460







3461











3462










790


3463







3464







3465







3466











3467










791
—C4H8


3468








3469









—C3H7





792


3470







3471








3472









—OC4H9





793
—C4H8O—


3473








3474











3475










794


3476







3477








3478









—C3H6OC3H7





795


3479







3480








3481









—CH2OC2H5





796


3482







3483







3484







3485









—C3H7





797
—C2H4O—


3486







3487







3488









—C5H11





798


3489







3490







3491







3492









—OC7H15





799


3493







3494







3495







3496











3497










800


3498







3499







3500







3501









—C3H7





801


3502







3503







3504







3505









—C5H11





802
—CH2O—


3506







3507







3508









—OC5H11





803


3509







3510







3511







3512









—C4H9





804


3513







3514







3515







3516









—C2H4OC3H7





805


3517







3518







3519







3520











3521










806
—C3H6


3522







3523







3524









—C3H7





807


3525







3526







3527







3528









—OC2H5





808
—C4H8O—


3529







3530







3531











3532










809


3533







3534







3535







3536









—CH2OC4H9





810


3537







3538







3539







3540









—CH2OC2H5





811


3541







3542








3543








3544







—C9H19





812
—CH2O—


3545








3546








3547







—C5H11





813
—C2H4


3548








3549








3550







—OCH3





814


3551







3552








3553








3554









3555










815


3556







3557








3558








3559







—C2H5





816


3560







3561








3562








3563







—C3H7





817
—C4H8


3564








3565








3566







—OC5H11





818
—C2H4O—


3567








3568








3569






—C4H9





819


3570







3571








3572








3573









3574










820



3575







3576








3577









3578










821
—C2H4


3579







3580







3581








3582






—C3H7





822


3583







3584







3585







3586








3587






—OC3H7





823
—C4H8O—


3588







3589







3590








3591








3592










824


3593







3594







3595







3596








3597






—CH2OC3H7





825


3598







3599







3600







3601








3602







—CH3





826


3603







3604








3605







3606







3607







—C3H7





827
—CH2O—


3608








3609







3610







3611







—C2H5





828
—C2H4


3612








3613







3614







3615







—OCH3





829


3616







3617








3618







3619







3620









3621










830


3622







3623








3624







3625







3626









3627










831
—C2H4


3628








3629







3630







3631







—C3H7





832


3632







3633








3634







3635







3636







—OC3H7





833
—C3H8O—


3637








3638







3639







3640








3641










834


3642







3643








3644







3645







3646







—C3H6OC2H5





835


3647







3648








3649







3650







3651







—CH3





836


3652







3653







3654







3655








3656







—C3H7





837
—C4H8


3657







3658







3659








3660







—OC3H7





838
—C2H4O—


3661







3662







3663








3664







—C2H5





839


3665







3666







3667







3668








3669









3670










840


3671







3672







3673







3674








3675









3676










841
—CH2


3677








3678








3679







—C10H21





842
—C2H4O—


3680








3681








3682







—C4H9





843
—C2H4


3683








3684








3685







—OC2H5





844


3686







3687








3688








3689









3690










845


3691







3692








3693








3694







—C2H5





846


3695







3696








3697








3698







—C3H7





847
—C4H8


3699








3700








3701







—OC6H13





848
—C2H4O—


3702








3703








3704







—C2H5





849


3705







3706








3707








3708









3709










850


3710







3711








3712








3713









3714










851
—C2H4


3715








3716







3717







3718







—C3H7





852


3719







3720








3721







3722







3723







—OC4H9





853
—C4H8O—


3724








3725







3726







3727









3728










854


3729







3730








3731







3732







3733







—C3H6OCH3





855


3734







3735








3736







3737







3738









3739










856


3740







3741







3742







3743








3744







—C3H7





857
—CH2O—


3745







3746







3747








3748







—C2H5





858
—C2H4


3749







3750







3751








3752







—OC3H7





859


3753







3754







3755







3756








3757









3758










860


3759







3760







3761







3762








3763









3764










861
—C2H4


3765








3766








3767







—C3H7





862


3768







3769








3770








3771







—OC7H15





863
—C4H8O—


3772








3773








3774









3775










864


3776







3777








3778








3779







—C2H4OC2H5





865


3780







3781








3782








3783







—CH3





866


3784







3785








3786








3787








3788





—C3H7





867
—C2H4


3789








3790








3791








3792





—OC3H7





868
—C2H4O—


3793








3794








3795








3796





—C2H5





869


3797







3798








3799








3800








3801







3802










870


3803







3804








3805








3806








3807







3808










871


3809







3810








3811








3812








3813





—C3H7





872
—CH2O—


3814








3815








3816








3817





—C5H11





873


3818







3819








3820








3821








3822





—OC2H5





874
—C4H8


3823








3824








3825








3826





—C3H7





875
—C3H6


3827








3828








3829








3830





—OC2H5





876


3831







3832








3833








3834








3835







3836










877


3837







3838








3839








3840








3841





—C2H5





878
—C2H4


3842








3843








3844








3845





—C3H7





879
—C4H8


3846








3847








3848








3849





—OCH3





880


3850







3851








3852








3853








3854







3855










881


3856







3857








3858








3859








3860





—CH3





882
—C4H8


3861








3862








3863








3864





—C3H7





883
—C3H6


3865








3866








3867








3868





—C2H4OC2H5





884


3869







3870








3871








3872








3873







3874










885


3875







3876








3877








3878








3879





—C6H13





886
—C2H4


3880








3881








3882







3883





—CH3





887
—CH2


3884








3885








3886








3887





—OCH3





888


3888







3889








3890








3891








3892







3893










889


3894







3895








3896








3897








3898





—C3H7





890
—C2H4


3899








3900








3901








3902





—C2H5





891
—CH2


3903








3904








3905








3906





—OC2H5





892


3907







3908








3909







3910








3911







3912










893


3913







3914








3915








3916








3917





—C3H7





894


3918







3919








3920








3921








3922





—C3H7





895
—CH2O—


3923








3924








3925








3926





—CH3





896


3927







3928








3929








3930








3931





—OC2H5





897
—C3H6


3932








3933








3934








3935





—C3H7





898
—C4H8


3936








3937








3938








3939





—OCH3





899


3940







3941








3942








3943








3944







3945










900


3946







3947








3948








3949








3950





—C8H17





901


3951







3952








3953









—C3H7





902
—CH2O—


3954








3955









—C5H11





903
—C2H4


3956








3957









—OC4H9





904


3958







3959








3960








3961







—C5H11





905
—C3H6O—


3962








3963








3964







—C3H7





906
—CH2


3965








3966








3967









3968










907


3969







3970








3971








3972







—C3H7





908
—C2H4O—


3973








3974








3975







—C5H11





909
—C2H4


3976








3977








3978









3979










910


3980







3981








3982








3983







—C2H5





911
—C3H6O—


3984








3985








3986







—C3H7





912
—C6H12


3987








3988








3989







—OC3H11





913


3990







3991








3992








3993







—C3H7





914
—C4H8O—


3994








3995








3996







—C5H11





915


3997







3998








3999








4000







—OCH3





916


4001







4002








4003









—C3H7





917
—C2H4O—


4004








4005









—C4H9





918
—C2H4


4006








4007









—OC6H13





919


4008







4009








4010








4011







—C5H11





920


4012







4013








4014








4015







—OC3H7





921


4016







4017








4018








4019







—CH3





922


4020







4021








4022








4023







—C3H7





923


4024







4025








4026








4027







—OC3H7





924


4028







4029








4030








4031







—CH3





925


4032







4033








4034








4035







—C2H5





926


4036







4037








4038








4039







—OC3H7





927


4040







4041








4042








4043







—C6H13





928


4044







4045








4046








4047







—C3H7





929


4048







4049








4050








4051







—OC5H11





930
—C4H8O—


4052








4053








4054









4055










931
—C2H4


4056








4057







4058







4059







—CH3





932
—CH2


4060








4061







4062







4063







—OC2H5





933


4064







4065








4066







4067







4068









4069










934


4070







4071








4072







4073







4074







—C3H7





935
—C3H6


4075







4076







4077








4078







—C3H7





936
—CH2


4079







4080







4081








4082







—OC4H9





937


4083







4084







4085







4086








4087









4088










938


4089







4090







4091







4092








4093







—C3H7





939


4094







4095








4096







4097







4098







—C2H5





940
—C3H6O—


4099








4100







4101







4102







—CH3





941


4103







4104








4105







4106







4107







—OC3H7





942
—C2H4


4108







4109







4110








4111







—C3H7





943
—C4H8


4112







4113







4114








4115







—OC2H5





944


4116







4117







4118







4119








4120









4121










945


4122







4123







4124







4125








4126







—C8H17





946
—C4H8


4127







4128







4129







4130







4131







—CH3





947
—CH2


4132







4133







4134







4135







4136







—OC2H5





948


4137







4138







4139







4140







4141







4142









4143










949


4144







4145







4146







4147







4148







4149







—C3H7





950
—C3H6


4150







4151







4152







4153







4154







—C4H9





951
—CH2


4155







4156







4157







4158







4159







—OC2H5





952
—C2H4O—


4160







4161







4162







4163







4164









4165










953


4166







4167







4168







4169







4170







4171







—C3H7





954


4172







4173








4174







4175







4176








4177





—C2H5





955
—C2H4O—


4178








4179







4180







4181








4182





—C2H5





956


4183







4184








4185







4186







4187








4188





—OC4H9





957


4189







4190







4191







4192








4193








4194





—C3H7





958
—C4H8


4195







4196







4197








4198








4199





—OC2H5





959
—C2H4


4200







4201







4202








4203








4204







4205










960


4206







4207







4208







4209








4210








4211





—C5H11





961
—C48


4212








4213











4214










962
—C5H10


4215







4216







4217











4218










963


4219







4220








4221








4222









4223










964


4224







4225







4226







4227











4228










965
—CH2


4229








4230








4231









4232










966
—CH3H6


4233







4234







4235











4236










967
—C2H4O—


4237








4238







4239








4240







4241










968
—C4H8


4242







4243








4244









4245










969
—C3H6O—


4246







4247







4248











4249










970


4250







4251







4252







4253











4254










971


4255







4256








4257








4258







4259







4260







4261










972
—C2H4


4262







4263







4264







4265







4266









4267










973
—C4H8


4268







4269







4270











4271










974
—C2H4


4272







4273







4274







4275







4276







4277







4278







4279










975


4280







4281







4282







4283











4284










976
—CH2


4285








4286








4287








4288





—F





977
—C3H6


4289








4290








4291








4292





—Cl





978
—C2H4


4293








4294








4295








4296





—OCF3





979
—CH2O—


4297








4298








4299








4300





—CF3





980
—C2H4


4301








4302








4303








4304





—OCHF2





981
—C3H6


4305








4306








4307








4308





—OCH2CF3





982
—C2H4


4309








4310








4311








4312





—F





983
—C3H6


4313








4314








4315








4316





—OCHF2





984
—C2H4


4317








4318








4319








4320





—F





985
—C3H6


4321








4322








4323








4324





—OCF3





986
—C2H4


4325








4326








4327








4328





—F





987
—C3H6


4329








4330








4331








4332





—Cl





988
—C2H4


4333








4334








4335








4336





—F





989
—C3H6


4337








4338








4339








4340





—OCHF2





990
—C2H4


4341








4342








4343








4344





—OCF3





991
—C2H4


4345








4346








4347








4348





—F










[0098] Examples in which the compounds of the present invention were used as the components for the compositions shall be shown below. The compounds used in the composition examples and the examples described later were represented by codes exhibited by definitions which were shown in the following Table 1.
3TABLE 1Method for Description of Compounds Using SymbolsR—(SiH3-Y1-)A1—Z1— . . . —Zn-An-X(—Y2)1)Left Terminal Group R—, SiH3-Y1-Symbol3)Bonding Group —Zn—SymbolCnH2n+1n-—C2H4—2CnH2n+1O—nO——C4H84CnH2n+1OCmH2m+1nOm-—COO—ECH2═CH—V——C≡C—TCH2═CHCnH2nVn-—CH═CH—VCnH2n+1CH═CHCmH2mnVm-—CF2O—CF2OCnH2n+1CH═CHCmH2mCH═CHCkH2knVmVk-—OCF2OCF2CF2═CH—VFF—CF2═CHCnH2nVFFn-SiH3CnH2nSin-2) Ring Structure -An-Symbol4) Right Terminal Group —X, —Y2Symbol4349B—F —Cl —CN—F —Cl —C4350B(F)—CF3—OCF3—OCF2H—CF3—OCF3 OCF2H4351B(F, F)—CnH2n+1—OCnH2n+1—CnH2nCH═CH2-n —On —EMe -nV4352H—CmH2mCH═CHCnH2n+1—CH═CF2—CnH2nCH═CF2-mVn —VFF -nVFF4353Ch—C≡C—CN—TC4354G4355Py4356B(2F, 3F)4357B(2CN, 3CN)5) Examples of DescriptionExample 1 3-H2B(F, F)B(F)-FExample 3 Si2-HB(F, F)-C43584359Example 2 Si1-HH-54360


[0099] In the examples, “%” represents “weight %”, and “part” represents “part by weight” unless otherwise described. When a cis-trans isomer is present in the compound, it means a trans type. When a left terminal group is not described, the group represents a hydrogen atom.



Example 5

[0100]

4



















Si2—HB(F, F)—C
(No. 459)
15.0% 



Si1—HH-5
(No. 742)
8.0%



1V2—BEB(F, F)—C

5.0%



3-HB—C

10.0% 



1-BTB-3

5.0%



2-BTB-1

10.0% 



3-HH-4

3.0%



3-HHB-1

11.0% 



3-HHB-3

9.0%



3-H2BTB-2

4.0%



3-H2BTB-3

4.0%



3-H2BTB-4

4.0%



3-HB(F)TB-2

6.0%



3-HB(F)TB-3

6.0%



NI = 74.1 (° C.)



η = 15.5 (mPa · s)



Δn = 0.150



Δε = 9.6



Vth = 1.81 (V)











[0101] When adding 0.8 part of CM33 to 100 parts of the composition described above, the pitch was 11.3 μm.



Example 6

[0102]

5



















Si2—HB(F, F)—C
(No. 459)
13.0% 



2O1—BEB(F)—C

5.0%



3O1—BEB(F)—C

15.0% 



4O1—BEB(F)—C

13.0% 



2-HHB(F)—C

15.0% 



3-HHB(F)—C

15.0% 



3-HB(F)TB-2

4.0%



3-HB(F)TB-3

4.0%



3-HB(F)TB-4

4.0%



3-HHB-1

8.0%



3-HHB—O1

4.0%



NI = 85.4 (° C.)



η = 80.2 (mPa · s)



Δn = 0.143



Δε = 31.1



Vth = 0.86 (V)












Example 7

[0103]

6



















Si3—HB(F, F)B(F)—F
(No. 189)
4.0%



5-PyB—F

4.0%



3-PyB(F)—F

4.0%



2-BB—C

5.0%



5-BB—C

5.0%



2-PyB-2

2.0%



3-PyB-2

2.0%



4-PyB-2

2.0%



6-PyB—O5

3.0%



6-PyB—O6

3.0%



6-PyB—O7

3.0%



6-PyB—O8

3.0%



3-PyBB—F

6.0%



4-PyBB—F

6.0%



5-PyBB—F

6.0%



3-HHB-1

6.0%



3-HHB-3

8.0%



2-H2BTB-2

4.0%



2-H2BTB-3

4.0%



2-H2BTB-4

5.0%



3-H2BTB-2

5.0%



3-H2BTB-3

5.0%



3-H2BTB-4

5.0%



NI = 93.2 (° C.)



η = 33.4 (mPa · s)



Δn = 0.198



Δε = 6.5



Vth = 2.26 (V)












Example 8

[0104]

7



















Si2—HHB(F)—OCF3
(No. 36)
5.0%



Si3—HHB(F)—OCF3
(No. 39)
5.0%



3-GB—C

10.0% 



2-BEB—C

12.0% 



3-BEB—C

4.0%



3-PyB(F)—F

6.0%



3-HEB—O4

8.0%



4-HEB—O2

6.0%



5-HEB—O1

6.0%



3-HEB—O2

5.0%



5-HEB—O2

4.0%



5-HEB-5

5.0%



4-HEB-5

5.0%



1O—BEB-2

4.0%



3-HHB-1

6.0%



3-HHEBB—C

3.0%



3-HBEBB—C

3.0%



5-HBEBB—C

3.0%



NI = 74.0 (° C.)



η = 39.5 (mPa · s)



Δn = 0.117



Δε = 10.7



Vth = 1.36 (V)












Example 9

[0105]

8



















Si4—HB(F)EB—OCF3
(No. 219)
3.0%



3-HB—C

18.0% 



1O1—HB—C

10.0% 



3-HB(F)—C

10.0% 



2-PyB-2

2.0%



3-PyB-2

2.0%



4-PyB-2

2.0%



1O1—HH-3

7.0%



2-BTB—O1

7.0%



3-HHB-1

7.0%



3-HHB—F

4.0%



3-HHB—O1

4.0%



3-HHB-3

8.0%



3-H2BTB-2

3.0%



3-H2BTB-3

3.0%



2-PyBH-3

4.0%



3-PyBH-3

3.0%



3-PyBB-2

3.0%



NI = 80.2 (° C.)



η = 18.3 (mPa · s)



Δn = 0.140



Δε = 8.3



Vth = 1.73 (V)












Example 10

[0106]

9



















Si2—HB(F, F)—C
(No. 459)
12.0% 



2-BEB(F)—C

5.0%



3-BEB(F)—C

4.0%



1V2—BEB(F, F)—C

10.0% 



3-HH—EMe

10.0% 



3-HB—O2

18.0% 



7-HEB—F

2.0%



3-HHEB—F

2.0%



5-HHEB—F

2.0%



3-HBEB—F

4.0%



2O1—HBEB(F)—C

2.0%



3-HB(F)EB(F)—C

2.0%



3-HBEB(F, F)—C

2.0%



3-HHB—F

4.0%



3-HHB—O1

4.0%



3-HHB-3

13.0% 



3-HEBEB—F

2.0%



3-HEBEB-1

2.0%



NI = 69.6 (° C.)



η = 31.6 (mPa · s)



Δn = 0.109



Δε = 24.1



Vth = 0.90 (V)












Example 11

[0107]

10



















Si2—HB(F, F)—C
(No. 459)
10.0% 



2-BEB(F)—C

5.0%



3-BEB(F)—C

4.0%



4-BEB(F)—C

12.0% 



1V2—BEB(F, F)—C

6.0%



3-HB—O2

10.0% 



3-HH-4

3.0%



3-HHB—F

3.0%



3-HHB-1

8.0%



3-HHB—O1

4.0%



3-HBEB—F

4.0%



3-HHEB—F

7.0%



5-HHEB—F

7.0%



3-H2BTB-2

4.0%



3-H2BTB-3

4.0%



3-H2BTB-4

4.0%



3-HB(F)TB-2

5.0%



NI = 81.3 (° C.)



η = 36.2 (mPa · s)



Δn = 0.133



Δε = 24.5



Vth = 1.12 (V)












Example 12

[0108]

11



















Si2—HB(2F3F)—O2
(No. 678)
6.0%



Si4—HB(2F3F)—O2
(No. 676)
6.0%



2-BEB—C

12.0% 



3-BEB—C

4.0%



4-BEB—C

6.0%



3-HB—C

28.0% 



4-HEB—O2

8.0%



5-HEB—O1

8.0%



3-HEB—O2

6.0%



5-HEB—O2

5.0%



3-HHB-1

7.0%



3-HHB—O1

4.0%



NI = 55.4 (° C.)



η = 27.6 (mPa · s)



Δn = 0.114



Δε = 9.3



Vth = 1.41 (V)












Example 13

[0109]

12



















Si2—HB(F)B(F, F)—F
(No. 193)
7.0%



2-BEB—C

10.0% 



5-BB—C

12.0% 



1-BTB-3

7.0%



2-BTB-1

10.0% 



1O—BEB-2

10.0% 



1O—BEB-5

12.0% 



2-HHB-1

4.0%



3-HHB—F

4.0%



3-HHB-1

7.0%



3-HHB—O1

4.0%



3-HHB-3

13.0% 



NI = 65.2 (° C.)



η = 20.6 (mPa · s)



Δn = 0.155



Δε = 6.9



Vth = 1.71 (V)












Example 14

[0110]

13



















Si2—HB(F, F)—C
(No. 459)
12.0% 



Si2—HHB(F, F)—OCF2H
(No. 41)
7.0%



Si3—HHB(F, F)—OCF2H
(No. 44)
7.0%



Si4—HHB(F, F)—OCF2H
(No. 45)
7.0%



2-HB—C

5.0%



3-HB—O2

15.0% 



2-BTB-1

3.0%



3-HHB-1

8.0%



3-HHB—F

4.0%



3-HHB—O1

5.0%



3-HHB-3

14.0% 



3-HHEB—F

4.0%



5-HHEB—F

4.0%



3-HHB(F, F)—F

5.0%



NI = 81.4 (° C.)



η = 24.9 (mPa · s)



Δn = 0.091



Δε = 7.3



Vth = 2.00 (V)












Example 15

[0111]

14



















Si2—HB(F)EB—OCF3
(No. 211)
4.0%



Si3—HB(F)EB—OCF3
(No. 224)
4.0%



Si2—HH—2V
(No. 738)
7.0%



3-BEB(F)—C

8.0%



3-HB—C

8.0%



V—HB—C

8.0%



3-HB—O2

3.0%



3-HH—2V

14.0% 



V2—HHB-1

15.0% 



3-HHB-1

5.0%



3-HHEB—F

7.0%



3-H2BTB-2

6.0%



3-H2BTB-3

6.0%



3-H2BTB-4

5.0%



NI = 101.0 (° C.)



η = 17.1 (mPa · s)



Δn = 0.130



Δε = 8.6



Vth = 2.18 (V)












Example 16

[0112]

15



















Si2—HB(F, F)—C
(No. 459)
24.0% 



V2—HB—C

12.0% 



1V2—HB—C

12.0% 



3-HB(F)—C

5.0%



2-BTB-1

2.0%



3-HH-4

8.0%



3-HH—VFF

6.0%



2-HHB—C

3.0%



3-HHB—C

6.0%



3-HB(F)TB-2

8.0%



3-H2BTB-2

5.0%



3-H2BTB-3

5.0%



3-H2BTB-4

4.0%



NI = 60.6 (° C.)



η = 19.3 (mPa · s)



Δn = 0.135



Δε = 12.8



Vth = 1.67 (V)












Example 17

[0113]

16



















Si2—HHB(2F, 3F)—O2
(No. 691)
7.0%



5-BEB(F)—C

5.0%



V—HB—C

11.0% 



5-PyB—C

6.0%



4-BB-3

11.0% 



3-HH—2V

10.0% 



5-HH—V

11.0% 



V2—HHB-1

15.0% 



3-HHB-1

9.0%



1V2—HBB-2

10.0% 



3-HHEBH-3

5.0%



NI = 91.1 (° C.)



η = 17.8 (mPa · s)



Δn = 0.116



Δε = 4.2



Vth = 2.53 (V)












Example 18

[0114]

17



















Si2—HB(F, F)—C
(No. 459)
10.0% 



1V2—BEB(F, F)—C

8.0%



3-HB—C

10.0% 



V2V—HB—C

4.0%



V2V—HH-3

19.0% 



3-HB—O2

4.0%



3-HHB-1

10.0% 



3-HHB-3

15.0% 



3-HB(F)TB-2

4.0%



3-HB(F)TB-3

4.0%



3-H2BTB-2

4.0%



3-H2BTB-3

4.0%



3-H2BTB-4

4.0%



NI = 87.6 (° C.)



η = 17.6 (mPa · s)



Δn = 0.121



Δε = 9.7



Vth = 1.91 (V)












Example 19

[0115]

18



















Si2—HB(F, F)—C
(No. 459)
10.0% 



V2—HB—TC

10.0% 



3-HB—TC

10.0% 



5-HB—C

7.0%



5-BB—C

3.0%



2-BTB-1

10.0% 



2-BTB—O1

5.0%



3-HH-4

5.0%



3-HHB-1

10.0% 



3-HHB-3

11.0% 



3-H2BTB-2

3.0%



3-H2BTB-3

3.0%



3-HB(F)TB-2

3.0%



5-BTB(F)TB-3

10.0% 



NI = 89.6 (° C.)



η = 14.5 (mPa · s)



Δn = 0.197



Δε = 8.5



Vth = 1.87 (V)












Example 20

[0116]

19



















Si2—HB(F, F)—C
(No. 459)
12.0% 



Si1—HH-5
(No. 742)
10.0% 



Si2—HH—2V
(No. 738)
10.0% 



1V2—BEB(F, F)—C

6.0%



3-HB—C

6.0%



2-BTB-1

10.0% 



5-HH—VFF

10.0% 



1-BHH—VFF

8.0%



1-BHH—2VFF

11.0% 



3-H2BTB-2

5.0%



3-H2BTB-3

4.0%



3-H2BTB-4

4.0%



3-HHB-1

4.0%



NI = 67.8 (° C.)



η = 12.7 (mPa · s)



Δn = 0.121



Δε = 8.5



Vth = 1.79 (V)












Example 21

[0117]

20



















Si2—HB(F, F)—C
(No. 459)
15.0% 



5-HBCF2OB(F, F)—C

3.0%



3-HB(F, F)CF2OB(F, F)—C

3.0%



3-HB—C

3.0%



2-BTB-1

10.0% 



5-HH—VFF

30.0% 



1-BHH—VFF

8.0%



1-BHH—2VFF

11.0% 



3-H2BTB-2

5.0%



3-H2BTB-3

4.0%



3-H2BTB-4

4.0%



3-HHB-1

4.0%



NI = 66.8 (° C.)



η = 13.0 (mPa · s)



Δn = 0.116



Δε = 7.0



Vth = 2.03 (V)












Example 22

[0118]

21



















Si3—HHB(F)—OCF3
(No. 39)
8.0%



Si4—HHB(F)—OCF3
(No. 38)
8.0%



Si2—HB(F, F)B(F)—F
(No. 188)
6.0%



Si3—HB(F, F)B(F)—F
(No. 189)
6.0%



2-HHB(F)—F

17.0% 



3-HHB(F)—F

17.0% 



2-H2HB(F)—F

10.0% 



3-H2HB(F)—F

5.0% 



5-H2HB(F)—F

10.0% 



5-HBB(F)—F

13.0% 



NI = 86.7 (° C.)



η = 29.8 (mPa · s)



Δn = 0.089



Δε = 6.6



Vth = 1.90 (V)











[0119] When adding 0.3 part of CN to 100 parts of the composition described above, the pitch was 78.7 μm.



Example 23

[0120]

22



















Si2—HHB(F, F)—OCF2H
(No. 41)
10.0% 



Si3—HHB(F, F)—OCF2H
(No. 44)
10.0% 



Si2—HB(F)B(F, F)—F
(No. 193)
9.0%



Si3—HB(F)B(F, F)—F
(No. 194)
9.0%



7-HB(F, F)—F

3.0%



3-HB—O2

7.0%



5-HHB(F)—F

10.0% 



5-HBB(F)—F

16.0% 



2-HBB—F

4.0%



3-HBB—F

4.0%



5-HBB—F

3.0%



3-HBB(F, F)—F

5.0%



5-HBB(F, F)—F

10.0% 



NI = 71.1 (° C.)



η = 31.5 (mPa · s)



Δn = 0.111



Δε = 7.7



Vth = 1.69 (V)












Example 24

[0121]

23



















Si2—HB(F, F)—C
(No. 459)
8.0%



Si1—HH-5
(No. 742)
6.0%



5-HB—CL

16.0% 



3-HH-4

6.0%



3-HH-5

4.0%



3-HHB—F

4.0%



3-HHB—CL

3.0%



4-HHB—CL

4.0%



3-HHB(F)—F

10.0% 



4-HHB(F)—F

9.0%



5-HHB(F)—F

9.0%



5-HBB(F)—F

4.0%



5-HBBH—1O1

3.0%



3-HHBB(F, F)—F

2.0%



4-HHBB(F, F)—F

3.0%



5-HHBB(F, F)—F

3.0%



3-HH2BB(F, F)—F

3.0%



4-HH2BB(F, F)—F

3.0%



NI = 100.8 (° C.)



η = 18.7 (mPa · s)



Δn = 0.089



Δε = 5.7



Vth = 2.25 (V)












Example 25

[0122]

24



















Si2-HHB (F)-OCF3
(No. 36)
8.0%



Si3-HHB (F)-OCF3
(No. 39)
8.0%



Si2-HB (F) EB-OCF3
(No. 211)
10.0% 



Si4-HB (F, F) B (F)-F
(No. 182)
10.0% 



Si4-HB (F) B (F, F)-F
(No. 191)
10.0% 



3-HHB (F, F)-F

9.0%



5-H2HB (F, F)-F

8.0%



3-HBB (F, F)-F

11.0% 



3-H2BB (F, F)-F

10.0% 



5-HHBB (F, F)-F

3.0%



5-HHEBB-F

2.0%



3-HH2BB (F, F)-F

3.0%



4-HBBH-101

4.0%



5-HBBH-101

4.0%



NI = 83.7 (° C.)



η = 38.0 (mPa · s)



Δn = 0.118



Δε = 11.1



Vth = 1.58 (V)











[0123] When adding 0.25 part of CM-43L to 100 parts of the composition described above, the pitch was 63.7 μm.



Example 26

[0124]

25



















Si2-HB (F, F)-C
(No. 459)
12.0% 



Si4-HHB (F)-OCF3
(No. 38)
5.0%



Si4-HB (F) EB-OCF3
(No. 219)
10.0% 



6-HB-F

9.0%



7-HB-F

7.0%



2-HHB-OCF3

7.0%



3-HHB-OCF3

7.0%



4-HHB-OCF3

7.0%



3-HH2B-OCF3

4.0%



5-HH2B-OCF3

4.0%



3-HHB (F, F)-OCF3

5.0%



3-HBB (F)-F

10.0% 



3-HH2B (F)-F

3.0%



3-HB (F) BH-3

3.0%



5-HBBH-3

3.0%



3-HHB (F, F)-OCF2H

4.0%



NI = 79.4 (° C.)



η = 22.3 (mPa · s)



Δn = 0.094



Δε = 8.8



Vth = 1.65 (V)












Example 27

[0125]

26



















Si2-HB (F, F) B (F)-F
(No. 188)
7.0%



Si3-HB (F, F) B (F)-F
(No. 189)
7.0%



Si4-HB (F, F) B (F)-F
(No. 182)
15.0% 



Si2-HB (F) B (F, F)-F
(No. 193)
10.0% 



Si3-HB (F) B (F, F)-F
(No. 194)
11.0% 



Si4-HB (F) B (F, F)-F
(No. 191)
11.0% 



2-HHB (F)-F

3.0%



4-HBB (F)-F

2.0%



3-H2BB (F)-F

10.0% 



5-HBB (F, F)-F

6.0%



2-HHB (F, F)-F

5.0%



3-HHB (F, F)-F

5.0%



4-HHB (F, F)-F

5.0%



3-HHB-F

3.0%



NI = 64.0 (° C.)



η = 41.6 (mPa · s)



Δn = 0.125



Δε = 11.1



Vth = 1.53 (V)












Example 28

[0126]

27



















Si2-HHB (F, F)-OCF2H
(No. 41)
10.0% 



Si4-HHB (F, F)-OCF2H
(No. 45)
10.0% 



Si2-HB (F) EB-OCF3
(No. 211)
3.0%



Si3-HB (F) EB-OCF3
(No. 224)
3.0%



Si4-HB (F) EB-OCF3
(No. 219)
3.0%



5-HB-CL

11.0% 



3-HH-4

8.0%



5-HBB (F, F)-F

15.0% 



3-HHB (F, F)-F

8.0%



3-HHEB (F, F)-F

10.0% 



3-HBEB (F, F)-F

5.0%



5-HBEB (F, F)-F

3.0%



3-HHBB (F, F)-F

6.0%



3-HHB-1

5.0%



NI = 85.7 (° C.)



η = 25.5 (mPa · s)



Δn = 0.100



Δε = 8.6



Vth = 1.70 (V)












Example 29

[0127]

28



















Si4-HB (F) B (F, F)-F
(No. 191)
4.0%



Si2-HH-2V
(No. 738)
6.0%



7-HB (F)-F

6.0%



5-H2B (F)-F

6.0%



3-HB-O2

4.0%



3-HH-4

6.0%



2-HHB (F)-F

11.0% 



3-HHB (F)-F

11.0% 



5-HHB (F)-F

11.0% 



2-HBB (F)-F

2.0%



3-HBB (F)-F

2.0%



3-HBB (F, F)-F

3.0%



2-HHBB (F, F)-F

4.0%



3-HHBB (F, F)-F

5.0%



3-HHEB-F

4.0%



5-HHEB-F

4.0%



3-HHB-1

7.0%



3-HHB-F

4.0%



NI = 97.3 (° C.)



η = 20.4 (mPa · s)



Δn = 0.086



Δε = 4.8



Vth = 2.34 (V)












Example 30

[0128]

29



















Si2-HHB (F)-OCF3
(No. 36)
10.0%



Si3-HHB (F)-OCF3
(No. 39)
10.0%



Si2-HB (F, F) B (F)-F
(No. 188)
15.0%



Si4-HB (F, F) B (F)-F
(No. 182)
15.0%



Si2-HB (F) B (F, F)-F
(No. 193)
16.0%



Si4-HB (F) B (F, F)-F
(No. 191)
16.0%



3-HH-4

 4.0%



5-H2HB (F, F)-F

 8.0%



3-HBB (F, F)-F

 3.0%



3-HHBB (F, F)-F

 3.0%



NI = 41.8 (° C.)



η = 34.8 (mPa · s)



Δn = 0.102



Δε = 12.2



Vth = 1.18 (V)












Example 31

[0129]

30



















Si2-HHB (F, F)-OCF2H
(No. 41)
10.0% 



Si4-HHB (F, F)-OCF2H
(No. 45)
10.0% 



Si2-HHB (F)-OCF3
(No. 36)
10.0% 



Si2-HB (F) EB-OCF3
(No. 211)
10.0% 



7-HB (F, F)-F

5.0%



3-H2HB (F, F)-F

2.0%



4-HHB (F, F)-F

5.0%



3-HBB (F, F)-F

10.0% 



4-HHEB (F, F)-F

3.0%



5-HHEB (F, F)-F

3.0%



2-HBEB (F, F)-F

3.0%



3-HBEB (F, F)-F

5.0%



5-HBEB (F, F)-F

3.0%



3-HGB (F, F)-F

15.0% 



3-HHBB (F, F)-F

6.0%



NI = 76.9 (° C.)



η = 39.0 (mPa · s)



Δn = 0.094



Δε = 14.5



Vth = 1.32 (V)












Example 32

[0130]

31



















Si2-HB (F, F) B (F)-F
(No. 188)
5.0%



Si3-HB (F, F) B (F)-F
(No. 189)
5.0%



Si4-HHB (F)-OCF3
(No. 38)
5.0%



5-H4HB (F, F)-F

7.0%



5-H4HB-OCF3

15.0% 



3-H4HB (F, F)-CF3

8.0%



5-H4HB (F, F)-CF3

10.0% 



3-HB-CL

6.0%



5-HB-CL

4.0%



2-H2BB (F)-F

5.0%



5-H2HB (F, F)-F

5.0%



3-HHB-OCF3

5.0%



3-H2HB-OCF3

5.0%



V-HHB (F)-F

5.0%



3-HHB (F)-F

5.0%



3-HBEB (F, F)-F

5.0%



NI = 60.5 (° C.)



η = 28.6 (mPa · s)



Δn = 0.093



Δε = 9.3



Vth = 1.64 (V)












Example 33

[0131]

32



















Si4-HHB (2F, 3F)-O2
(No. 693)
3.0%



Si1-HH-5
(No. 742)
5.0%



Si2-HH-2V
(No. 738)
5.0%



5-HB-CL

17.0% 



7-HB (F, F)-F

3.0%



3-HH-5

5.0%



3-HB-O2

15.0% 



3-H2HB (F, F)-F

5.0%



4-H2HB (F, F)-F

5.0%



3-HHB (F, F)-F

6.0%



2-HHB (F)-F

7.0%



3-HHB (F)-F

7.0%



5-HHB (F)-F

7.0%



3-HHB-1

5.0%



3-HHB-O1

5.0%







NI = 70.6 (° C.)



η = 14.0 (mPa · s)



Δn = 0.074



Δε = 2.5



Vth = 2.45 (V)












Example 34

[0132]

33



















Si3-HHB (F)-OCF3
(No. 39)
10.0% 



Si4-HHB (F)-OCF3
(No. 38)
9.0%



Si2-HHB (F, F)-OCF2H
(No. 41)
8.0%



Si2-HB (F, F) B (F)-F
(No. 188)
10.0% 



Si4-HB (F) B (F, F)-F
(No. 191)
10.0% 



5-HB-CL

4.0%



7-HHB (F)-F

9.0%



4-HHB (F, F)-F

3.0%



3-H2HB (F, F)-F

12.0% 



3-HBB (F, F)-F

2.0%



2-HHBB (F, F)-F

6.0%



3-GHB (F, F)-F

3.0%



4-GHB (F, F)-F

8.0%



5-GHB (F, F)-F

6.0%



NI = 66.8 (° C.)



η = 39.4 (mPa · s)



Δn = 0.089



Δε = 10.6



Vth = 1.18 (V)












Example 35

[0133]

34



















Si2—HHB(F)—OCF3
(No. 36)
7.0%



Si4—HHB(F)—OCF3
(No. 38)
7.0%



Si3—HB(F)EB—OCF3
(No. 224)
10.0% 



Si3—HB(F, F)B(F)—F
(No. 189)
7.0%



Si3—HB(F)B(F, F)—F
(No. 194)
7.0%



3-HHB(F)—F

8.0%



3-HHB(F, F)—F

8.0%



3-HBB(F, F)—F

7.0%



3-H2HB(F, F)—F

10.0% 



4-HHEB(F, F)—F

3.0%



2-HBEB(F, F)—F

2.0%



3-HBEB(F, F)—F

3.0%



3-GHB(F, F)—F

3.0%



4-GHB(F, F)—F

7.0%



5-GHB(F, F)—F

7.0%



3-HHBB(F, F)—F

4.0%



NI = 70.5 (° C.)



η = 41.0 (mPa · s)



Δn = 0.092



Δε = 12.3



Vth = 1.16 (V)












Example 36

[0134]

35



















Si2—HB(F, F)—C
(No. 459)
4.0%



Si3—HB(F)EB—OCF3
(No. 224)
5.0%



Si4—HHB(F, F)—OCF2H
(No. 45)
6.0%



Si2—HHB(F)—OCF3
(No. 36)
4.0%



7-HB(F)—F

3.0%



5-HB—CL

3.0%



3-HH-4

9.0%



3-HH—EMe

23.0% 



3-HHEB(F, F)—F

10.0% 



3-HHEB—F

8.0%



5-HHEB—F

8.0%



4-HGB(F, F)—F

5.0%



3-H2GB(F, F)—F

5.0%



5-GHB(F, F)—F

7.0%



NI = 81.0 (° C.)



η = 22.5 (mPa · s)



Δn = 0.069



Δε = 6.7



Vth = 1.41 (V)












Example 37

[0135]

36



















Si2—HB(F)B(F, F)—F
(No. 193)
10.0% 



Si3—HB(F)B(F, F)—F
(No. 194)
10.0% 



Si4—HB(F)B(F, F)—F
(No. 191)
10.0% 



3-H2HB(F, F)—F

5.0%



5-H2HB(F, F)—F

5.0%



5-HBB(F, F)—F

30.0% 



5-HBB(F)B-2

10.0% 



5-HBB(F)B-3

10.0% 



3-BB(F)B(F, F)—F

5.0%



5-B2B(F, F)B(F)—F

5.0%



NI = 94.0 (° C.)



η = 52.1 (mPa · s)



Δn = 0.148



Δε = 11.3



Vth = 1.66 (V)












Example 38

[0136]

37



















Si2—HHB(F, F)—OCF2H
(No. 41)
6.0%



Si2—HB(F)EB—OCF3
(No. 211)
8.0%



Si2—HH—2V
(No. 738)
10.0% 



3-HB(F, F)CF2OB(F, F)—F

11.0% 



5-HB(F, F)CF2OB(F, F)—F

11.0% 



5-HB—CL

7.0%



3-HH-4

4.0%



2-HH-5

4.0%



3-HHB-1

4.0%



3-HHEB—F

6.0%



5-HHEB—F

6.0%



4-HHB(F, F)—F

3.0%



4-HHEB(F, F)—F

3.0%



5-HHEB(F, F)—F

2.0%



2-HBEB(F, F)—F

3.0%



3-HBEB(F, F)—F

3.0%



5-HBEB(F, F)—F

3.0%



2-HHBB(F, F)—F

3.0%



3-HHBB(F, F)—F

3.0%



NI = 81.0 (° C.)



η = 22.1 (mPa · s)



Δn = 0.083



Δε = 9.0



Vth = 1.38 (V)












Example 39

[0137]

38



















Si2—HHB(F)—OCF3
(No. 36)
5.0%



Si2—HB(F, F)B(F)—F
(No. 188)
5.0%



Si2—HB(F)B(F, F)—F
(No. 193)
5.0%



3-BB(F, F)CF2OB(F, F)—F

35.0% 



3-HH-4

8.0%



3-HHB(F, F)—F

5.0%



3-H2HB(F, F)—F

9.0%



3-HBB(F, F)—F

5.0%



2-HHBB(F, F)—F

3.0%



3-HHBB(F, F)—F

3.0%



3-HH2BB(F, F)—F

4.0%



3-HHB-1

6.0%



5-HBBH—1O1

7.0%



NI = 76.7 (° C.)



η = 29.8 (mPa · s)



Δn = 0.114



Δε = 12.8



Vth = 1.36 (V)












Example 40

[0138]

39



















Si2—HB(2F, 3F)—O2
(No. 678)
7.0%



Si4—HB(2F, 3F)—O2
(No. 676)
7.0%



3-HEB—O4

28.0% 



4-HEB—O2

20.0% 



5-HEB—O1

20.0% 



3-HEB—O2

18.0% 



NI = 64.7 (° C.)



η = 19.8 (mPa · s)



Δn = 0.089












Example 41

[0139]

40



















Si2—HB(2F, 3F)—O2
(No. 678)
12.0% 



Si4—HB(2F, 3F)—O2
(No. 676)
11.0% 



Si2—HHB(2F, 3F)—O2
(No. 691)
14.0% 



Si4—HHB(2F, 3F)—O2
(No. 693)
15.0% 



Si2—HHB(2F, 3F)-2
(No. 694)
14.0% 



3-HH-2

5.0%



3-HH-4

6.0%



3-HH—O1

4.0%



3-HH—O3

5.0%



5-HH—O1

4.0%



3-HHB(2F, 3F)-2

10.0% 



NI = 74.0 (° C.)



Δn = 0.080



Δε = −4.0












Example 42

[0140]

41



















Si2—HB(2F, 3F)—O2
(No. 678)
10.0% 



Si4—HB(2F, 3F)—O2
(No. 676)
10.0% 



Si2—HHB(2F, 3F)—O2
(No. 691)
12.0% 



Si4—HHB(2F, 3F)—O2
(No. 693)
13.0% 



Si2—HHB(2F, 3F)-2
(No. 694)
4.0%



3-HH-5

5.0%



3-HH-4

5.0%



3-HH—O1

6.0%



3-HH—O3

6.0%



3-HB—O1

5.0%



3-HB—O2

5.0%



2-HHB(2F, 3F)-1

4.0%



3-HHEH-3

5.0%



3-HHEH-5

5.0%



4-HHEH-3

5.0%



NI = 78.5 (° C.)



Δn = 0.077



Δε = −3.3












Example 43

[0141]

42



















Si2—HB(F, F)—C
(No. 459)
5.0%



3-BB(2F, 3F)—O2

12.0% 



3-BB(2F, 3F)—O4

10.0% 



5-BB(2F, 3F)—O4

10.0% 



2-BB(2F, 3F)B-3

20.0% 



3-BB(2F, 3F)B-5

13.0% 



5-BB(2F, 3F)B-5

14.0% 



5-BB(2F, 3F)B-7

16.0% 



NI = 66.4 (° C.)



Δn = 0.190



Δε = −1.9












Example 44

[0142]

43



















Si2—HB(F, F)B(F)—F
(No. 188)
3.0%



Si2—HB(F)B(F, F)—F
(No. 193)
3.0%



3-HB—O1

15.0% 



3-HB—O2

6.0%



3-HEB(2F, 3F)—O2

9.0%



4-HEB(2F, 3F)—O2

9.0%



5-HEB(2F, 3F)—O2

9.0%



2-BB2B—O2

6.0%



3-BB2B—O2

6.0%



5-BB2B—O1

6.0%



1-B2BB(2F)-5

7.0%



3-B2BB(2F)-5

7.0%



5-B(F)BB—O2

7.0%



3-BB(2F, 3F)B-3

7.0%



NI = 75.4 (° C.)



η = 24.2 (mPa · s)



Δn = 0.155












Example 45

[0143]

44



















Si4-HHB (F)-OCF3
(No. 38)
5.0%



3-HH-O1

8.0%



5-HH-O1

4.0%



3-HH-4

5.0%



3-HB (2F, 3F)-O2

16.0%



5-HB (2F, 3F)-O2

21.0%



3-HHB (2F, 3F)-1

7.0%



3-HHB (2F, 3F)-O2

14.0%



5-HHB (2F, 3F)-O2

20.0%










NI =
61.0 (° C.)



η =
23.8 (mPa · s)



Δn =
0.076



Δε =
−3.5












Example 46

[0144]

45



















Si2-HB (2F, 3F)-O2
(No. 678)
12.0%



Si4-HB (2F, 3F)-O2
(No. 676)
12.0%



Si2-HHB (2F, 3F)-1
(No. 692)
12.0%



Si2-HHB (2F, 3F)-2
(No. 694)
12.0%



Si2-HHB (2F, 3F)-O2
(No. 691)
13.0%



Si4-HHB (2F, 3F)-O2
(No. 693)
13.0%



3-HB-O1

15.0%



3-HH-4

5.0%



3-HHB-1

6.0%










NI =
74.5 (° C.)



η =
38.3 (mPa · s)



Δn =
0.090



Δε =
−3.4












Example 47

[0145]

46



















Si2-HB (2F, 3F)-O2
(No. 678)
12.0%



Si4-HB (2F, 3F)-O2
(No. 676)
12.0%



Si2-HHB (2F, 3F)-1
(No. 692)
12.0%



Si2-HHB (2F, 3F)-2
(No. 694)
12.0%



3-HB-O1

15.0%



3-HH-4

5.0%



3-HHB (2F, 3F)-O2

13.0%



5-HHB (2F, 3F)-O2

13.0%



6-HEB (2F, 3F)-O2

6.0%










NI =
74.2 (° C.)



η =
36.2 (mPa · s)



Δn =
0.087



Δε =
−3.7












Example 48

[0146]

47



















Si2-HB (2F, 3F)-O2
(No. 678)
3.0%



Si4-HHB (2F, 3F)-O2
(No. 693)
3.0%



3-HB-O2

20.0%



1O1-HH-3

6.0%



1O1-HH-5

5.0%



3-HH-EMe

12.0%



4-HEB-O1

9.0%



4-HEB-O2

7.0%



5-HEB-O1

8.0%



3-HHB-1

6.0%



3-HHB-3

6.0%



3-HEB (2 CN, 3CN)-O5

4.0%



4-HEB (2 CN, 3CN)-O5

3.0%



5-HEB (2 CN, 3CN)-O5

2.0%



2-HBEB (2CN, 3CN)-O2

2.0%



4-HBEB (2CN, 3CN)-O4

4.0%










NI =
70.4 (° C.)



η =
30.7 (mPa · s)



Δn =
0.080



Δε =
−5. 4



Vth =
1.60 (V)











[0147] Effects of the Invention


[0148] The compounds of the present invention, that is, the di- to tetracyclic compounds having SiH3 at a terminal are sufficiently stable physically and chemically under the condition where the a liquid crystal display device is usually used. It is characterized by having a good mutual solubility, a low viscosity and a low threshold voltage. Further, addition of the compound of the present invention makes it possible, as shown in the examples, to provide a liquid crystal composition and a liquid crystal display which have good characteristics and are novel.


Claims
  • 1. A silicon compound represented by formula (1):
  • 2. The silicon compound defined in claim 1, wherein in formula (1) described in claim 1, p and q are 0; A1 and A2 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z1 is a single bond, —(CH2)2—, —CH═CH—, —C≡C—, —(CH2)4—, —COO—, —OCO—, —OCF2—, or —CF2O—.
  • 3. The silicon compound defined in claim 1, wherein in formula (1) described in claim 1, p is 1; q is 0; A1, A2 and A3 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —S—,1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z1 and Z2 each are independently a single bond, —(CH2)2—, —CH═CH—, —C≡C—, —COO—, —OCO—, —(CH2)4—, —OCF2—, or —CF2O—.
  • 4. The silicon compound defined in claim 1, wherein in formula (1) described in claim 1, p and q are 1; A1, A2, A3, and A4 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —S—,1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z1, Z2 and Z3 each are independently a single bond, —(CH2)2—, —CH═CH—, —C≡C—, —COO—, —OCO—, —(CH2)4—, —OCF2—, or —CF2O—.
  • 5. The silicon compound defined in claim 1, wherein in formula (1) described in claim 1, Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in the alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH3 are not adjacent; Y2 is alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O—, —CH═CH— or —C≡C—, but —O— and —O— are not adjacent; and A1, A2, A3, and A4 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene, or pirimidine-2,5-diyl.
  • 6. The silicon compound defined in claim 1, wherein in formula (1) described in claim 1, Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in the alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH3 are not adjacent; Y2 is halogen, —CN, —C≡C—CN, or alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O—, but —O— and —O— are not adjacent, and at least one hydrogen is replaced by halogen; and A1, A2, A3, and A4 each are independently 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —S—,1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by halogen, or pirimidine-2,5-diyl.
  • 7. The silicon compound defined in claim 1, wherein in formula (1) described in claim 1, Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in the alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH3 are not adjacent; Y2 is alkyl having 1 to 10 carbon, in which any —CH2— in the alkyl may be replaced by —O—, —S— or —CH═CH—, but —O— and —O—, —S— and —S— or —O— and —S— are not adjacent; A1, A2, A3 and A4 each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH2— are replaced by —O—, 1,4-phenylene in which a 2-position is replaced by halogen, 1,4-phenylene in which a 3-position is replaced by halogen, or 1,4-phenylene in which a 2-position and a 3-position are replaced by halogen, and one of A1, A2 A3, and A4 is always 1,4-phenylene in which a 2-position or a 3-position is replaced by halogen or 1,4-phenylene in which a 2-position and a 3-position are replaced by halogen.
  • 8. A liquid crystal composition comprising at least one silicon compound defined in any one of claims 1 to 7.
  • 9. The liquid crystal composition defined in claim 8, comprising at least one silicon compound described in any one of claims 1 to 7 as a first component and at least one compound selected from the group of compounds represented by formulas (2), (3) and (4) as a second component:
  • 10. The liquid crystal composition defined in claim 8, comprising at least one silicon compound described in any one of claims 1 to 7 as the first component and at least one compound selected from the group of compounds represented by formulas (5) and (6) as a second component:
  • 11. The liquid crystal composition defined in claim 8, comprising at least one silicon compound described in any one of claims 1 to 7 as the first component and at least one compound selected from the group of compounds represented by formulas (7), (8) and (9) as a second component:
  • 12. The liquid crystal composition defined in claim 8, comprising at least one silicon compound described in any one of claims 1 to 7 as the first component, at least one compound selected from the group of the compounds represented by formulas (2), (3) and (4) described in claim 9 as the second component, and at least one compound selected from the group of compounds represented by formulas (10), (11) and (12) as a third component:
  • 13. The liquid crystal composition defined in claim 8, comprising at least one silicon compound described in any one of claims 1 to 7 as the first component, at least one compound selected from the group of the compounds represented by formulas (5) and (6) described in claim 10 as the second component, and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) described in claim 12 as the third component.
  • 14. The liquid crystal composition defined in claim 8, comprising at least one silicon compound described in any one of claims 1 to 7 as the first component, at least one compound selected from the group of the compounds represented by formulas (7), (8) and (9) described in claim 11 as the second component and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) described in claim 12 as the third component.
  • 15. The liquid crystal composition defined in claim 8, comprising at least one silicon compound described in any one of claims 1 to 7 as the first component, at least one compound selected from the group of the compounds represented by formulas (2), (3) and (4) described in claim 9 as the second component, at least one compound selected from the group of the compounds represented by formulas (5) and (6) described in claim 10 as the third component, and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) described in claim 12 as a fourth component.
  • 16. A liquid crystal composition comprising at least one liquid crystal composition defined in claims 8 and further comprising at least one optically active compound.
  • 17. A liquid crystal display using the liquid crystal composition defined in any of claims 8 to 15.
Priority Claims (1)
Number Date Country Kind
2001-57164 Mar 2001 JP