Silicon compound, liquid crystal composition and liquid crystal display

Information

  • Patent Grant
  • 6703083
  • Patent Number
    6,703,083
  • Date Filed
    Thursday, February 28, 2002
    22 years ago
  • Date Issued
    Tuesday, March 9, 2004
    20 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): wherein Y1 is, for example, alkylene having 1 to 10 carbon atoms, Y2 is, for example, hydrogen, halogen, —CN, —C≡C—CN, or alkyl having 1 to 10 carbon atoms; A1, A2, A3, and A4 each are, for example, independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, or 1,4-phenylene; 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.
Description




BACKGROUND OF THE INVENTION




1. Field of the Invention




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 SiH


3


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.




2. Description of the Related Art




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.




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 (Δ∈), a viscosity (η), a conductivity and an elastic constant ratio K


33


/K


11


(K


33


: bend elastic constant and K


11


: 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.




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.




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:











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:











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 solubility with the other compositions.




SUMMARY OF THE INVENTION




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.




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




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











wherein Y


1


is alkylene having 1 to 10 carbon, in which any —CH


2


— 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 SiH


3


, or —S— and SiH


3


are not adjacent, and at least one hydrogen in the alkylene may be replaced by halogen or —CN; Y


2


is hydrogen, halogen, —CN, —C≡C—CN, or alkyl having 1 to 10 carbon, in which any —CH


2


— in the alkyl may be replaced by —O—, —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; A


1


, A


2


, A


3


, and A


4


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 —CH


2


— 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═; Z


1


, Z


2


and Z


3


each are independently a single bond, —(CH


2


)


2


—, —OCH


2


—, —CH


2


O—, —CH═CH—, —C≡C—, —(CH


2


)


4


—, —O(CH


2


)


3


—, —(CH


2


)


3


O—, —COO—, —OCO—, —OCF


2


—, or —CF


2


O—; and p and q each are independently 0 or 1.




[2] The silicon compound defined in the above item [1], wherein in formula (1) described above, p and q are 0; A


1


and A


2


each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH


2


— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z


1


is a single bond, —(CH


2


)


2


—, —CH=CH—, —C=C—, —(CH


2


)


4


—, —COO—, —OCO—, —OCF


2


—, or —CF


2


O—.




[3] The silicon compound defined in the above item [1], wherein in formula (1) described above, p is 1, and q is 0; A


1


, A


2


and A


3


each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH


2


— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z


1


and Z


2


each are independently a single bond, —(CH


2


)


2


—, —CH═CH—, —C≡C—, —COO—, —OCO—, —(CH


2


)


4


—, —OCF


2


—, or —CF


2


O—.




[4] The silicon compound defined in the above item [1], wherein in formula (1) described above, p and q are 1; A


1


, A


2


, A


3


, and A


4


each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH


2


— are replaced by —O—, 1,4-phenylene, 1,4-phenylene in which any hydrogen is replaced by halogen, or pirimidine-2,5-diyl; and Z


1


, Z


2


and Z


3


each are independently a single bond, —(CH


2


)


2


—, —CH═CH—, —C≡C—, —COO—, —OCO—, —(CH


2


)


4


—, —OCF


2


—, or —CF


2


O—.




[5] The silicon compound defined in the above item [1], wherein in formula (1) described above, Y


1


is alkylene having 1 to 10 carbon, in which any —CH


2


— in this alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH


3


are not adjacent; Y


2


is alkyl having 1 to 10 carbon, in which any —CH


2


— in the alkyl may be replaced by —O—, —CH═CH— or —C≡C—, but —O— and —O— are not adjacent; and A


1


, A


2


, A


3


, and A


4


each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH


2


— are replaced by —O—, 1,4-phenylene, or pirimidine-2,5-diyl.




[6] The silicon compound defined in the above item [1], wherein in formula (1) described above, Y


1


is alkylene having 1 to 10 carbon, in which any —CH


2


— in the alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH


3


are not adjacent; Y


2


is halogen, —CN, —C≡C—CN or alkyl having 1 to 10 carbon, in which any —CH


2


— 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 A


1


, A


2


, A


3


, and A


4


each are independently 1,4-cyclohexylene in which one or more non-adjacent —CH


2


— 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.




[7] The silicon compound defined in the above item [1], wherein in formula (1) described above, Y


1


is alkylene having 1 to 10 carbon, in which any —CH


2


— in the alkylene may be replaced by —O— or —CH═CH—, but —O— and —O— or —O— and SiH


3


are not adjacent; Y


2


is alkyl having 1 to 10 carbon, in which any —CH


2


— 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; A


1


, A


2


, A


3


, and A


4


each are independently 1,4-cyclohexylene, 1,4-cyclohexylene in which one or more non-adjacent —CH


2


— 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 A


1


, A


2


, A


3


, and A


4


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 the items [1] to [7].




[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:











wherein R


1


is alkyl having 1 to 10 carbon, in which any —CH


2


— 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; X


1


is fluorine, Chlorine, —OCF


3


, —OCF


2


H, —CF


3


, —CF


2


H, —CFH


2


, —OCF


2


CF


2


H, or —OCF


2


CFHCF


3


; L


1


and L


2


each are independently hydrogen or fluorine; Z


4


and Z


5


each are independently —(CH


2


) 2—, —(CH


2


)


4


—, —COO—, —CF


2


O—, —OCF


2


—, —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.




[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:











wherein R


2


and R


3


each are independently alkyl having 1 to 10 carbon, in which any —CH


2


— 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; X


2


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; Z


6


is —(CH


2


)


2


—, —COO—, —CF


2


O—, —OCF


2


—, or a single bond; L


3


, L


4


and L


5


each are independently hydrogen or fluorine; and a, b and c each are independently 0 or 1.




[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:











wherein R


4


and R


5


each are independently alkyl having 1 to 10 carbon, in which any —CH


2


— 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; L


6


, L


7


, L


8


and L


9


each are independently hydrogen or fluorine, and all of them are not hydrogen simultaneously; and Z


7


and Z


8


each are independently —(CH


2


)


2


—, —COO— or a single bond.




[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:











wherein R


6


and R


7


each are independently alkyl having 1 to 10 carbon, in which any —CH


2


— 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 Z


9


and Z


10


each are independently —C≡C—, —COO—, —(CH


2


)


2


—, —CH═CH— or a single bond.




[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.




[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.




[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.




[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.




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




The compound (1) of the present invention is a compound having a SiH


3


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.



































































































































































































Y


1


and Y


2


mean the same as those described in the item [1] described above.




Capable of being given as preferred Y


1


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, methyleneoxyproeylene, ethyleneoxypropylene, vinylene, 1-propenylene, 2-propenylene, 1-butenylene, 2-butenylene, 3-butenylene, 2-prpenyleneoxy and 2-butenyleneoxy.




Capable of being given as preferred Y


2


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-pentenyloxy, 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, —CF


3


, —OCF


3


and —OCF


2


H.




The compound in which one or both of Y


1


and Y


2


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.




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.




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 Δ∈.




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.




The compound (1) which is substituted with groups such as —F, —CN, —CF


3


, —OCF


3


and —OCF


2


H so that the dipole moment grows larger in a molecular long axis direction has a large positive Δ∈, 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 Δ∈. Further, the compound in which plural groups are substituted on a benzene ring shows a larger Δ∈.




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 Δ∈, 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 Δ∈. The compound having two or more —F shows a particularly large negative Δ∈.




The compound (1) having double bonds on Z


1


, Z


2


or Z


3


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 Δ∈.




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.




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.




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 controlling a threshold voltage, a liquid crystal phase temperature range, a birefringence, a dielectric anisotropy and a viscosity.




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.




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).



























































































































































In the formulas, R


1


and X


1


mean the same as those described in the item [9] described above.




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.




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.



































































In the formulas, R


2


, R


3


and X


2


mean the same as those described in the item [10] described above.




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.




When preparing a composition having a negative dielectric anisotropy which is suited for a vertical aligning 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.



























In the formulas, R


4


and R


5


mean the same as those described in the item [11] described above).




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.




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.




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.




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.











































In the formulas, R


6


and R


7


mean the same as those 5 described in the item [12] described above.




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.




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.




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.











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.




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).




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).




Routes shown below can be given as the specific examples.











Y


1


, Y


2


, A


1


, A


2


, A


3


, A


4


, Z


1


, Z


2


, Z


3


, p and q each described above are the same as those described in the item [1] described above. Q


1


is halogen, and Q


2


is halogen or alkoxy. Mt is lithium, potassium, halogenated magnesium or halogenated zinc.




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 SiQ


2




3


.











EXAMPLES




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




Production of trans-1-pentyl-4-(trans-4-silylmethylcyclohexyl)cyclohexane (compound (No. 742) in which in Formula (1), Y


1


is methylene; Y


2


is pentyl; A


1


and A


2


are trans-1,4-cyclohexylene; Z


1


is a single bond; p and q are 0)




First Step:




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.




Second Step:




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 MS: m/e=280 (M+).




Example 2




Production of 1-trifluoromethoxy-4-(trans-4-(trans-4-silylethylcyclohexyl)cyclohexyl)benzene (compound (No. 34) in which in Formula (1), Y


1


is ethylene;. Y


2


is —OCF


3


; A


1


and A


2


are trans-1,4-cyclohexylene; A


3


is 1,4-phenylene; Z


1


and Z


2


are single bonds; p is 1, and q is 0)




First Step:




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.




Second Step:




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-4-silylethylcyclohexyl)cyclohexyl)benzene (26 mmole).




MS: m/e=384 (M+).




Example 3




Production of 1-ethoxy-2,3-difluoro-4-(trans-4-silylbutylcyclohexyl)benzene (compound (No. 676) in which in Formula (1), Y


1


is butylene; Y


2


is ethoxy; A


1


is trans-1,4-cyclohexylene, and A


2


is 2,3-difluoro-1,4-phenylene; Z


1


is a single bond; p and q are 0)




First Step:




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-4-trimethoxysilyl-butylcyclohexyl)benzene (58 mmole) was obtained by distillation under reduced pressure.




Second Step:




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). MS: m/e=326 (M+).




Example 4




Production of 2-fluoro-1-(4-propylphenyl)-4-(4-silylethylphenyl)benzene (compound (No. 861) in which in Formula (1), Y


1


is ethylene; Y


2


is propyl; A


1


and A


3


are 1,4-phenylene; A


2


is 2-fluoro-1,4-phenylene; Z


1


and Z


2


are single bonds; p is 1, and q is 0)




First Step:




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.




Second Step:




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). MS: m/e=348 (M+).




The following compounds were produced according to the methods of Examples 1 to 4.




















Y


1






A


1






Z


1






A


2













 1






















































 2




—CH


2


O—










































 3






















































 4




—C


4


H


8













































 5




—C


3


H


6


O—










































 6






















































 7






















































 8






















































 9






















































 10






















































 11






















































 12






















































 13






















































 14






















































 15




—CH


2


O—










































 16





























































 17




—CH


2


O—

















































 18




—C


3


H


6


O—

















































 19





























































 20





























































 21





























































 22





























































 23





























































 24





























































 25





























































 26




—C


2


H


4


O—

















































 27





























































 28





























































 29




—CH


2




















































 30





























































 31






















































 32




—CH


2


O—










































 33






















































 34






















































 35






















































 36






















































 37




—C


2


H


4


O—










































 38






















































 39




—C


3


H


6













































 40






















































 41




—C


2


H


4













































 42






















































 43






















































 44




—C


3


H


6













































 45






















































 46






















































 47






















































 48




—CH


2


O—










































 49






















































 50






















































 51






















































 52






















































 53






















































 54




—C


3


H


6


O—










































 55






















































 56






















































 57






















































 58






















































 59




—CH


2













































 60




—C


2


H


4


O—










































 61





























































 62





























































 63





























































 64





























































 65





























































 66






















































 67






















































 68






















































 69




—C


3


H


6


O—










































 70






















































 71






















































 72






















































 73






















































 74




—CH


2













































 75




—C


2


H


4


O—










































 76





























































 77





























































 78





























































 79




—CH


2


O—

















































 80





























































 81





























































 82




—C


3


H


6


O—

















































 83





























































 84





























































 85





























































 86





























































 87





























































 88





























































 89




—CH


2




















































 90




—C


2


H


4


O—

















































 91





























































 92





























































 93




—CH


2


O—

















































 94





























































 95





























































 96





























































 97




—C


3


H


8


O—

















































 98





























































 99





























































100





























































101





























































102





























































103





























































104




—CH


2




















































105





























































106






















































107






















































108






















































109






















































110






















































111






















































112






















































113






















































114




—CH


2


O—










































115






















































116




—C


2


H


4


O—










































117




—CH


2













































118






















































119






















































120




—C


3


H


6


O—










































121





























































122





























































123





























































124





























































125





























































126





























































127





























































128





























































129




—CH


2


O—

















































130





























































131




—C


2


H


4


O—

















































132




—C


2


H


4




















































133





























































134





























































135




—C


3


H


6


O—

















































136





























































137





























































138





























































139





























































140





























































141






















































142






















































143






















































144




—CH


2


O—










































145






















































146




—C


2


H


4


O—

















































147




—C


4


H


8




















































148





























































149





























































150





























































151






















































152






















































153




—CH


2


O—










































154






















































155






















































156






















































157






















































158






















































159




—CH


2


O—










































160






















































161






















































162






















































163






















































164




—CH


2













































165




—C


2


H


4


O—










































166






















































167




—CH


2


O—










































168






















































169






















































170






















































171






















































172






















































173






















































174






















































175




—C


3


H


6


O—










































176






















































177






















































178






















































179




—C


2


H


4


O—










































180




—C


4


H


8













































181






















































182






















































183






















































184






















































185






















































186






















































187






















































188






















































189




—C


3


H


6













































190




—CH


2


O—










































191






















































192




—CH


2













































193






















































194






















































195






















































196





























































197





























































198





























































199





























































200





























































201





























































202




—CH


2




















































203





























































204





























































205




—CH


2


O—

















































206





























































207




—CH


2




















































208





























































209





























































210





























































211






















































212






















































213




—CH


2


O—










































214






















































215






















































216






















































217






















































218






















































219






















































220




—CH


2













































221






















































222






















































223






















































224




—C


3


H


6













































225






















































226






















































227






















































228






















































229






















































230






















































231






















































232






















































233






















































234






















































235




—CH


2


O—










































236






















































237






















































238






















































239






















































240




—C


4


H


8













































241






















































242






















































243






















































244






















































245






















































246






















































247






















































248






















































249






















































250




—C


3


H


6


O—

















































251





























































252





























































253





























































254





























































255





























































256






















































257






















































258






















































259






















































260






















































261




—C


3


H


6


O—










































262






















































263






















































264




—C


2


H


4













































265






















































266






















































267






















































268






















































269




—CH


2













































270






















































271






















































272






















































273






















































274






















































275






















































276




—C


3


H


6


O—










































277






















































278




—C


2


H


4













































279






















































280






















































281






















































282






















































283






















































284




—CH


2


O—










































285






















































286






















































287






















































288






















































289






















































290






















































291






















































292






















































293




—C


2


H


4













































294






















































295






















































296






















































297




—C


3


H


6


O—










































298






















































299




—CH


2


O—










































300






















































301






















































302






















































303






















































304






















































305






















































306




—C


3


H


6


O—










































307






















































308






















































309




—C


2


H


4













































310






















































311






















































312






















































313




—C


2


H


4













































314






















































315




—CH


2













































316




—C


2


H


4













































317




—CH


2


O—










































318






















































319




—C


4


H


8













































320






















































321






















































322






















































323






















































324




—C


2


H


4













































325






















































326




—C


2


H


4


O—










































327






















































328





























































329




—CH


2




















































330





























































331




—C


4


H


8




















































332




—C


2


H


4




















































333




—C


3


H


6


O—

















































334





























































335





























































336




—C


2


H


4




















































337






















































338






















































339






















































340






















































341




—C


4


H


8













































342






















































343






















































344




—CH


2













































345






















































346




—C


2


H


4













































347




—C


3


H


6













































348






















































349






















































350






















































351






















































352






















































353






















































354




—CH


2


O—










































355






















































356




—C


2


H


4


O—










































357






















































358






















































359




—CH


2













































360






















































361




—C


2


H


4













































362




—C


3


H


6













































363






















































364






















































365




—CH


2


O—










































366






















































367






















































368




—C


2


H


4


O—










































369






















































370






















































371






















































372






















































373






















































374




—CH


2













































375






















































376




—C


2


H


4













































377




—C


3


H


6













































378




—CH


2


O—










































379






















































380






















































381






















































382






















































383




—C


5


H


10


O—










































384






















































385






















































386






















































387






















































388






















































389




—CH


2













































390






















































391






















































392




—C


3


H


6













































393




—C


2


H


4













































394






















































395




—C


2


H


4













































396




—CH


2


O—










































397




—C


2


H


4


O—










































398






















































399






















































400






















































401






















































402






















































403






















































404




—CH


2













































405






















































406




—C


2


H


4













































407




—CH


2


O—










































408






















































409




—C


2


H


4













































410




—C


2


H


4













































411




—C


3


H


6


O—










































412






















































413






















































414






















































415






















































416






















































417






















































418






















































419




—CH


2













































420






















































421






















































422






















































423




—CH


2


O—










































424






















































425






















































426




—C


2


H


4


O—










































427






















































428






















































429






















































430






















































431




—CH


2













































432






















































433






















































434




—C


3


H


6













































435




—C


2


H


4













































436






















































437






















































438






















































439




—C


2


H


4


O—










































440






















































441




—CH


2













































442






















































443






















































444






















































445






















































446






















































447






















































448




—CH


2


O—










































449




—C


3


H


6













































450




—C


2


H


4













































451




—C


4


H


8













































452




—C


3


H


6


O—










































453






















































454




—C


4


H


8













































455




—C


5


H


10


O—










































456






















































457




—C


4


H


8













































458






















































459






















































460






















































461




—C


2


H


4


O—










































462





























































463




—CH


2


O—

















































464





























































465





























































466




—C


4


H


8













































467




—C


3


H


6


O—










































468






















































469




—C


4


H


8













































470






















































471




—C


2


H


4


O—










































472






















































473






















































474






















































475




—CH


2


O—










































476






















































477






















































478




—C


4


H


8













































479




—C


5


H


10


O—










































480






















































481




—C


2


H


4




















































482




—C


3


H


6


O—

















































483





























































484




—C


2


H


4




















































485





























































486




—C


2


H


4


O—

















































487





























































488





























































489




—C


3


H


6




















































490




—C


3


H


6


O—

















































491





























































492





























































493




—CH


2


O—

















































494





























































495





























































496




—C


2


H


4




















































497




—C


3


H


6


O—

















































498





























































499





























































500




—C


2


H


4


O—

















































501





























































502





























































503




—C


3


H


6


O—

















































504




—C


3


H


6




















































505





























































506





























































507





























































508




—CH


2


O—

















































509





























































510





























































511




—C


2


H


4




















































512




—C


3


H


6


O—

















































513





























































514




—C


2


H


4


O—

















































515





























































516





























































517





























































518




—C


3


H


6


O—

















































519




—C


3


H


6




















































520





























































521





























































522




—CH


2


O—

















































523





























































524





























































525




—C


3


H


6


O—

















































526






















































527




—CH


2


O—










































528






















































529






















































530




—C


2


H


4


O—










































531






















































532






















































533




—C


3


H


6


O—










































534






















































535






















































536




—C


2


H


4


O—










































537




—CH


2













































538






















































539




—CH


2


O—










































540






















































541




—C


2


H


4













































542




—C


3


H


6


O—










































543






















































544




—C


4


H


8













































545




—C


2


H


4


O—










































546




—C


3


H


6













































547






















































548




—C


3


H


6


O—










































549






















































550






















































551




—C


2


H


4


O—










































552




—CH


2













































553






















































554




—CH


2


O—










































555






















































556




—C


2


H


4













































557




—CH


2


O—










































558






















































559




—C


7


H


14




















































560




—C


3


H


6


O—

















































561




—C


3


H


6




















































562





























































563




—C


2


H


4


O—

















































564





























































565





























































566




—C


2


H


4


O—

















































567




—C


2


H


4




















































568





























































569





























































570




—CH


2


O—

















































571




—C


2


H


4




















































572




—CH


2


O—

















































573





























































574




—C


2


H


4




















































575




—C


3


H


6


O—

















































576




—C


3


H


6




















































577






















































578




—C


3


H


6


O—










































579






















































580






















































581




—C


2


H


4


O—










































582




—C


2


H


4













































583






















































584






















































585




—CH


2


O—










































586




—C


2


H


4













































587




—C


2


H


4


O—










































588






















































589




—C


4


H


8













































590




—C


3


H


6


O—










































591




—C


2


H


4













































592






















































593




—C


3


H


6


O—










































594






















































595






















































596






















































597




—CH


2


O—










































598






















































599




—C


2


H


4


O—










































600




—C


3


H


6













































601




—C


2


H


4













































602




—C


3


H


6


O—










































603






















































604




—C


4


H


8













































605




—C


2


H


4


O—










































606




—C


2


H


4













































607




—C


8


H


16













































608




—C


3


H


6


O—










































609




—CH


2


O—










































610






















































611






















































612




—C


2


H


4













































613






















































614




—C


2


H


4


O—










































615




—C


3


H


6













































616




—C


4


H


8













































617




—C


4


H


8


O—










































618






















































619




—C


2


H


4













































620




—C


2


H


4


O—










































621




—C


4


H


8













































622






















































623




—C


2


H


4


O—










































624




—CH


2


O—










































625






















































626




—CH


2


O—










































627




—C


2


H


4













































628






















































629




—C


2


H


4


O—










































630




—C


3


H


6













































631




—C


4


H


8




















































632





























































633




—C


4


H


8




















































634




—CH


2


O—

















































635




—C


2


H


4




















































636




—C


4


H


8




















































637




—C


4


H


8




















































638




—C


2


H


4


O—

















































639





























































640





























































641




—C


2


H


4




















































642




—C


2


H


4




















































643





























































644




—C


4


H


8




















































645





























































646




—C


4


H


8




















































647





























































648




—C


3


H


6


O—

















































649




—CH


2


O—










































650




—C


2


H


4













































651




—C


4


H


8













































652




—C


2


H


4













































653




—C


2


H


4


O—










































654






















































655






















































656




—C


4


H


8


O—










































657




—C


2


H


4













































658






















































659




—CH


2


O—










































660




—C


2


H


4













































661




—C


4


H


8













































662






















































663




—C


2


H


4













































664




—CH


2


O—










































665




—C


4


H


8













































666




—C


2


H


4













































667




—C


2


H


4













































668




—C


6


H


12


O—










































669






















































670






















































671




—C


5


H


10













































672






















































673






















































674




—C


4


H


8


O—










































675






















































676






















































677




—C


3


H


6













































678






















































679




—C


4


H


8


O—










































680






















































681




—C


4


H


8













































682




—C


3


H


6


O—










































683




—C


7


H


14













































684






















































685






















































686





























































687





























































688




—CH


2


O—

















































689





























































690





























































691






















































692




—C


2


H


4













































693




—C


4


H


8













































694






















































695






















































696




—C


4


H


8













































697




—C


3


H


6


O—










































698




—C


7


H


14













































699




—C


2


H


4













































700






















































701






















































702






















































703




—CH


2


O—










































704






















































705






















































706






















































707




—C


2


H


4













































708






















































709




—C


3


H


6


O—










































710






















































711




—C


2


H


4













































712




—CH


2


O—










































713




—C


4


H


8













































714






















































715






















































716






















































717






















































718




—C


2


H


4













































719






















































720






















































721






















































722




—C


4


H


8













































723






















































724




—C


3


H


6


O—










































725






















































726




—C


2


H


4













































727




—CH


2


O—










































728




—C


4


H


8













































729






















































730






















































731






















































732






















































733




—C


7


H


14













































734




—C


3


H


6


O—










































735






















































736






















































737




—CH


2


O—










































738






















































739






















































740






















































741




—C


7


H


14


O—










































742




—CH


2













































743






















































744




—C


2


H


4


O—










































745






















































746





























































747





























































748





























































749





























































750





























































751




—C


3


H


6




















































752




—CH


2


O—

















































753





























































754





























































755





























































756






















































757




—C


2


H


4


O—










































758






















































759






















































760






















































761






















































762




—C


6


H


12













































763






















































764






















































765






















































766






















































767






















































768






















































769





























































770




—C


2


H


4


O—

















































771





























































772





























































773





























































774





























































775





























































776




—C


4


H


8


O—

















































777





























































778




—CH


2




















































779





























































780





























































781





























































782




—C


2


H


4


O—

















































783





























































784





























































785





























































786





























































787




—CH


2




















































788




—C


2


H


4


O—

















































789





























































790





























































791




—C


4


H


8













































792






















































793




—C


4


H


8


O—










































794






















































795






















































796





























































797




—C


2


H


4


O—

















































798





























































799





























































800





























































801





























































802




—CH


2


O—

















































803





























































804





























































805





























































806




—C


3


H


6



















—≡—

























807




























—≡—

























808




—C


4


H


8


O—
















—≡—

























809




























—≡—

























810




























—≡—

























811






















































812




—CH


2


O—










































813




—C


2


H


4













































814






















































815






















































816






















































817




—C


4


H


8













































818




—C


2


H


4


O—










































819






















































820











































821




—C


2


H


4




















































822





























































823




—C


4


H


8


O—

















































824





























































825





























































826






















































827




—CH


2


O—










































828




—C


2


H


4













































829






















































830






















































831




—C


2


H


4













































832






















































833




—C


3


H


8


O—










































834






















































835






















































836





























































837




—C


4


H


8




















































838




—C


2


H


4


O—

















































839





























































840





























































841




—CH


2













































842




—C


2


H


4


O—










































843




—C


2


H


4













































844






















































845






















































846






















































847




—C


4


H


8













































848




—C


2


H


4


O—










































849






















































850






















































851




—C


2


H


4













































852






















































853




—C


4


H


8


O—










































854






















































855






















































856





























































857




—CH


2


O—

















































858




—C


2


H


4




















































859





























































860





























































861




—C


2


H


4













































862






















































863




—C


4


H


8


O—










































864






















































865






















































866






















































867




—C


2


H


4













































868




—C


2


H


4


O—










































869






















































870






















































871






















































872




—CH


2


O—










































873






















































874




—C


4


H


8













































875




—C


3


H


8













































876






















































877






















































878




—C


2


H


4













































879




—C


4


H


8













































880




—CH


2


O—










































881






















































882




—C


4


H


8













































883




—C


3


H


6













































884






















































885






















































886




—C


2


H


4













































887




—CH


2













































888






















































889






















































890




—C


2


H


4













































891




—CH


2













































892




—CH


2


O—










































893






















































894






















































895




—CH


2


O—










































896






















































897




—C


3


H


6













































898




—C


4


H


8













































899






















































900






















































901






















































902




—CH


2


O—










































903




—C


2


H


4













































904






















































905




—C


3


H


6


O—










































906




—CH


2













































907






















































908




—C


2


H


4


O—










































909




—C


2


H


4













































910






















































911




—C


3


H


6


O—










































912




—C


6


H


12













































913






















































914




—C


4


H


8


O—










































915






















































916






















































917




—C


2


H


4


O—










































918




—C


2


H


4













































919






















































920






















































921






















































922






















































923






















































924






















































925






















































926






















































927






















































928






















































929






















































930




—C


4


H


8


O—










































931




—C


2


H


4













































932




—CH


2













































933






















































934






















































935




—C


3


H


6




















































936




—CH


2




















































937




—CH


2


O—

















































938





























































939






















































940




—C


3


H


6


O—










































941






















































942




—C


2


H


4




















































943




—C


4


H


8




















































944





























































945





























































946




—C


4


H


8




















































947




—CH


2




















































948





























































949





























































950




—C


3


H


6




















































951




—CH


2




















































952




—C


2


H


4


O—

















































953





























































954






















































955




—C


2


H


4


O—










































956






















































957





























































958




—C


4


H


8




















































959




—C


2


H


4




















































960





























































961




—C


4


H


8













































962




—C


5


H


10




















































963






















































964





























































965




—CH


2













































966




—C


3


H


6




















































967




—C


2


H


4


O—










































968




—C


4


H


8




















































969




—C


3


H


6


O—

















































970




























—≡—

























971






















































972




—C


2


H


4



















—≡—

























973




—C


4


H


8




















































974




—C


2


H


4



















—≡—

























975





























































976




—CH


2













































977




—C


3


H


6













































978




—C


2


H


4













































979




—CH


2


O—










































980




—C


2


H


4













































981




—C


3


H


6













































982




—C


2


H


4













































983




—C


3


H


6













































984




—C


2


H


4













































985




—C


3


H


6













































986




—C


2


H


4













































987




—C


3


H


6













































988




—C


2


H


4













































989




—C


3


H


6













































990




—C


2


H


4













































991




—C


2


H


4































































Z


2






A


3






Z


3






A


4






Y


2













 1








—F






 2








—Cl






 3








—OCF


2


H






 4








—OCF


3








 5








—F






 6








—OCF


2


H






 7








—CF


3








 8








—F






 9








—OCF


3








 10








—F






 11








—CF


3








 12








—OCF


3








 13








—F






 14








—OCF


2


H






 15








—F






 16








—OCF


3








 17








—OCF


2


CF


3








 18








—CF


3








 19








—OCF


3








 20








—F






 21








—OCF


2


H






 22








—CF


3








 23








—F






 24








—OCF


3








 25








—F






 26








—CF


2


H






 27








—OCF


3








 28








—F






 29








—OCF


2


H






 30








—F













 31























—F













 32























—Cl













 33























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3















 34























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3















 35























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 36























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3















 37























—CF


3















 38























—OCF


3















 39























—OCF


3















 40























—F













 41























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2


H













 42























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3















 43























—F













 44























—OCF


2


H













 45























—OCF


2


H













 46






























—OCF


2


H













 47






























—F













 48






























—CF


3















 49






























—OCF


3















 50






























—F













 51






























—OCF


3















 52






























—CF


2


H













 53






























—F













 54






























—OCF


3















 55






























—F













 56






























—OCF


3















 57






























—OCF


3















 58






























—F













 59






























—OCF


2


H













 60






























—F













 61








—OCF


3








 62








—F






 63








—OCF


3








 64








—F






 65








—F













 66






























—OCF


3















 67






























—Cl













 68






























—OCF


3















 69






























—F













 70






























—F













 71






























—F













 72






























—OCF


3















 73






























—F













 74






























—OCF


2


H













 75






























—F













 76























—Cl













 77























—OCF


3















 78























—CF


2


H













 79























—OCF


3















 80























—F













 81























—OCF


3















 82























—OCF


2


H













 83























—F













 84























—OCF


3















 85























—F













 86























—CF


3















 87























—OCF


3















 88























—F













 89























—OCF


2


H













 90























—F













 91























—F













 92























—OCF


3















 93























—CF


2


H













 94























—OCF


3















 95























—F













 96























—OCF


2


H













 97























—OCF


2


H













 98























—F













 99























—OCF


3















100























—F













101























—OCF


2


H













102























—OCF


3















103























—F













104























—CF


3















105























—F













106























—F













107























—Cl













108























—OCF


3















109























—OCF


3















110























—F













111























—OCF


3















112























—OCF


2


H













113























—F













114























—OCF


3















115























—F













116























—CF


3















117























—OCF


3















118























—F













119























—OCF


2


H













120























—F













121























—OCF


3















122























—Cl













123























—F













124























—OCF


3















125























—F













126























—OCF


3















127























—CF


2


H













128























—F













129























—OCF


3















130























—F













131























—OCF


3















132























—OCF


3















133























—F













134























—OCF


2


H













135























—F













136























—OCF


3















137























—F













138























—OCF


3















139























—OCF


3















140























—F













141






























—OCF


3















142






























—OCF


2


H













143






























—OCF


3















144






























—F













145






























—F













146























—F













147























—OCF


3















148























—F













149























—OCF


3















150























—F













151






























—OCF


3















152






























—F













153






























—CF


3















154






























—OCF


3















155






























—F













156






























—OCF


3















157






























—CF


3















158






























—F













159






























—OCF


3















160






























—F













161






























—OCF


3















162






























—OCF


3















163






























—F













164






























—OCF


2


H













165






























—F













166






























—OCF


3















167






























—F













168






























—CF


3















169






























—OCF


3















170






























—F













171






























—OCF


3















172






























—OCF


2


H













173






























—F













174






























—OCF


3















175






























—F













176






























—OCF


3















177






























—OCF


3















178






























—F













179






























—OCF


2


H













180






























—F













181























—OCF


3















182























—F













183























—CF


3















184























—OCF


3















185























—F













186























—OCF


3















187























—OCF


2


H













188























—F













189























—F













190























—OCF


3















191























—F













192























—OCF


3















193























—F













194























—F













195























—F













196























—OCF


3















197























—F













198























—F













199























—OCF


3















200























—F













201























—OCF


3















202























—CF


2


H













203























—F













204























—OCF


3















205























—OCF


3















206























—F













207























—OCF


3















208























—F













209























—F













210























—F













211






























—OCF


3















212






























—F













213






























—CF


3















214






























—OCF


3















215






























—F













216






























—OCF


3















217






























—OCF


2


CFHCF


3















218






























—F













219






























—OCF


3















220






























—OCF


3















221






























—F













222






























—OCF


3















223






























—F













224






























—OCF


3















225






























—F













226























—F













227























—Cl













228























—OCF


3















229























—F













230























—OCF


3















231























—OCF


2


H













232























—F













233























—F













234























—OCF


3















235























—F













236























—OCF


3















237























—OCF


3















238























—F













239























—OCF


3















240























—CF


3















241























—F













242























—F













243























—OCF


3















244























—F













245























—OCF


3















246























—OCF


2


H













247























—F













248























—F













249























—OCF


3















250























—F













251























—OCF


3















252























—OCF


3















253























—F













254























—OCF


3















255























—CF


3















256






























—OCF


3















257






























—F













258






























—CF


3















259






























—OCF


3















260






























—F













261






























—OCF


3















262






























—CF


3















263






























—F













264






























—OCF


3















265






























—F













266






























—OCF


3















267






























—OCF


3















268






























—F













269






























—OCF


2


H













270






























—F













271






























—OCF


3















272






























—F













273






























—CF


3















274






























—OCF


3















275






























—F













276






























—Cl













277






























—CF


3















278






























—F













279






























—OCF


3















280






























—F













281






























—OCF


3















282






























—F













283






























—F













284






























—OCF


2


H













285






























—OCF


3















286






























—OCF


3















287






























—F













288






























—CF


3















289






























—F













290






























—F













291






























—OCF


3















292






























—CF


2


H













293






























—F













294






























—OCF


3















295






























—Cl













296






























—OCF


3















297






























—F













298






























—F













299






























—OCF


2


H













300






























—OCF


3















301






























—OCF


3















302






























—F













303






























—CF


3















304






























—OCF


3















305






























—F













306






























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307






























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2


H













308






























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309






























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3















310






























—F













311






























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3















312






























—OCF


3















313






























—F













314






























—OCF


2


H













315






























—F













316























—F













317























—Cl













318























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3















319























—OCF


3















320























—F













321























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3















322























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3















323























—F













324























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3















325























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326























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2















327























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3















328























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329























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2


H













330























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3















331























—F













332























—OCF


3















333























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3















334























—OCF


3















335























—F













336























—F













337























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3















338























—F













339























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3















340























—F













341























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3















342























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3















343























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344























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2


H













345























—F













346






































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347






































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348






































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3















349






































—OCF


3















350






































—F













351






































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3















352






































—CF


3















353






































—F













354






































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3















355






































—F













356






































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3















357






































—OCF


3















358






































—F













359






































—CF


2


H













360






































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3















361






































—F













362






































—CFH


2















363






































—OCF


3















364






































—OCF


3















365






































—F













366






































—OCF


2


H













367






































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3















368






































—F













369






































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3















370






































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371






































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3















372






































—OCF


3















373






































—F













374






































—CF


2


H













375






































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3















376






































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377






































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2















378






































—OCF


3















379






































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3















380






































—F













381






































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3















382













































—CF


3















383













































—F













384













































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3















385













































—F













386













































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3















387













































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3















388













































—F













389













































—CF


2


H













390













































—OCF


3















391













































—F













392













































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2















393













































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3















394













































—F













395













































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3















396













































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2


H













397













































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3















398













































—F













399













































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3















400













































—F













401













































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3















402













































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3















403













































—F













404













































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2


H













405













































—OCF


3















406













































—F













407













































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2


H













408













































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3















409













































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3















411













































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2















412













































—CF


3















413













































—F













414













































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3















415













































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3















417













































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3















418













































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2


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3















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3















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2


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3















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3















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3















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2


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3















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2















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3















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3















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2


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3















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3















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2


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3















448













































—F













449













































—OCFH


2















450













































—OCF


3















451








—CN






452








—CN






453








—CN






454








—CN






455








—CN






456








—CN






457








—≡—CN






458








—CN






459








—CN






460








—CN






461








—≡—CN






462








—CN






463








—CN






464








—CN






465








—CN






466








—CN






467








—CN






468








—CN






469








—≡—CN






470








—CN






471








—CN






472








—CN






473








—≡—CN






474








—CN






475








—CN






476








—CN






477








—≡—CN






478








—CN






479








—CN






480








—≡—CN






481








—CN






482








—CN






483








—CN






484








—≡—CN






485








—CN






486








—CN






487








—CN






488








—≡—CN






489








—CN






490








—CN






491








—CN






492








—CN






493








—CN






494








—CN






495








—≡—CN






496








—CN






497








—CN






498








—≡—CN






499








—CN






500








—CN






501








—CN






502








—CN






503








—CN






504








—≡—CN






505








—CN






506








—CN






507








—≡—CN






508








—CN






509








—CN






510








—CN






511








—CN






512








—CN






513








—CN






514








—CN






515








—≡—CN






516








—CN






517








—CN






518








—CN






519








—CN






520








—≡—CN






521








—CN






522








—CN






523








—≡—CN






524








—CN






525








—CN













526























—CN













527























—CN













528























—≡—CN













529























—CN













530























—CN













531























—≡—CN













532























—CN













533























—CN













534























—CN













535























—CN













536























—CN













537























—≡—CN













538























—CN













539























—CN













540























—≡—CN













541























—CN













542























—CN













543























—≡—CN













544























—CN













545























—CN













546























—≡—CN













547























—CN













548























—CN













549























—≡—CN













550






























—CN













551






























—CN













552






























—≡—CN













553






























—CN













554






























—CN













555






























—≡—CN













556






























—CN













557






























—CN













558






























—≡—CN













559























—CN













560























—CN













561























—≡—CN













562























—CN













563























—CN













564























—≡—CN













565























—CN













566























—CN













567























—≡—CN













568























—CN













569























—CN













570























—≡—CN













571























—CN













572























—CN













573























—≡—CN













574























—CN













575























—CN













576























—CN













577






























—CN













578






























—CN













579






























—≡—CN













580






























—CN













581






























—CN













582






























—≡—CN













583






























—CN













584






























—CN













585






























—≡—CN













586






























—CN













587






























—CN













588






























—≡—CN













589






























—CN













590






























—CN













591






























—≡—CN













592






























—CN













593






























—CN













594






























—CN













595






























—CN













596






























—CN













597






























—≡—CN













598






























—CN













599






























—CN













600






























—≡—CN













601






























—CN













602






























—CN













603






























—≡—CN













604






























—CN













605






























—CN













606






























—≡—CN













607






























—CN













608






























—CN













609






























—≡—CN













610






























—CN













611






























—CN













612






























—≡—CN













613






























—CN













614






























—CN













615






























—≡—CN













616






























—CN













617






























—CN













618






























—≡—CN













619






























—CN













620






























—CN













621






























—≡—CN













622






























—CN













623






























—CN













624






























—≡—CN













625













































—CN













626













































—CN













627













































—≡—CN













628













































—CN













629













































—CN













630













































—≡—CN













631








—F






632








—OCF


3








633








—CF


3








634








—OCF


2


H






635








—CN






636








—≡—CN






637








—F






638








—F






639








—OCF


3








640








—CF


2


H






641








—CN






642








—≡—CN






643








—F






644








—OCF


3








645








—OCF


3








646








—CF


3








647








—CN






648








—≡—CN













649






























—CN













650






























—CN













651






























—≡—CN













652






























—CN













653






























—CN













654






























—≡—CN













655






























—CN













656






























—CN













657






























—≡—CN













658













































—CN













659













































—CN













660













































—≡—CN













661













































—CN













662













































—CN













663













































—CN













664













































—CN













665













































—≡—CN













666













































—CN













667








—F






668








—F






669








—F






670








—F






671








—F






672








—F













673























—F













674























—F













675























—F













676








—OC


2


H


5








677








—CH


3








678








—OC


2


H


5








679








—C


3


H


7








680








—OC


3


H


7








681








—OC


2


H


5








682








—C


2


H


5








683








—SCH


3








684








—OC


2


H


5








685








—C


4


H


9








686








—OC


2


H


5








687








—C


3


H


7








688








—OC


3


H


7








689








—OCH


3








690








—C


5


H


11















691























—OC


2


H


5















692























—CH


3















693























—OC


2


H


5















694























—C


2


H


5















695























—OC


3


H


7















696






























—OC


2


H


5















697






























—C


2


H


5















698






























—OCH


3















699






























—OC


2


H


5















700






























—C


4


H


9















701






























—OC


2


H


5















702






























—C


3


H


7















703






























—OC


3


H


7















704






























—OCH


3















705






























—C


5


H


11















706























—OC


2


H


5















707























—C


3


H


7















708























—OCH


3















709























—C


6


H


13















710























—OC


2


H


5















711






























—OC


2


H


5















712






























—CH


3















713






























—OCH


3















714






























—SC


2


H


5















715






























—C


4


H


9















716






























—OC


2


H


5















717






























—C


3


H


7















718























—OC


2


H


5















719























—C


3


H


7















720























—OC


2


H


5















721























—OC


2


H


5















722























—CH


3















723























—OC


3


H


7















724























—C


6


H


13















725























—OC


2


H


5















726























—OC


2


H


5















727























—SCH


3















728























—C


2


H


5















729























—OC


2


H


5















730























—CH


3















731






























—OC


2


H


5















732






























—CH


3















733






























—OC


2


H


5















734






























—C


3


H


7















735






























—OC


2


H


5















736








—C


4


H


9








737








—C


7


H


15















738





























739





























740








—C


5


H


11








741








—OC


8


H


17








742








—C


5


H


11








743








—COOCH


3








744








—COOC


2


H


5








745








—COOC


3


H


7








746








—C


5


H


11








747








—OC


4


H


9















748





























749








—C


2


H


5















750





























751








—C


2


H


5








752








—C


8


H


17















753





























754





























755








—C


3


H


7








756








—C


3


H


7








757








—C


4


H


9















758





























759








—OC


5


H


11















760





























761








—C


5


H


11








762








—CH


2


OCH


3








763








—C


2


H


5















764





























765








—OC


2


H


5








766








—OC


6


H


13








767








—C


8


H


17















768





























769








—C


3


H


7








770








—C


4


H


9








771








—C


5


H


11








772








—OC


7


H


15















773





























774





























775








—C


5


H


11








776








—C


2


H


5








777








—C


4


H


9








778








—C


2


H


4


OCH


3















779





























780





























781








—C


3


H


7








782








—C


6


H


13








783








—OC


7


H


15















784





























785








—C


3


H


7








786








—C


3


H


7








787








—OC


5


H


11








788








—C


6


H


13















789





























790





























791








—C


3


H


7








792








—OC


4


H


9















793





























794








—C


3


H


6


OC


3


H


7








795








—CH


2


OC


2


H


5








796








—C


3


H


7








797








—C


5


H


11








798








—OC


7


H


15















799





























800








—C


3


H


7








801








—C


5


H


11








802








—OC


6


H


11








803








—C


4


H


9








804








—C


2


H


4


OC


3


H


7















805





























806








—C


3


H


7








807








—OC


2


H


5















808





























809








—CH


2


OC


4


H


9








810








—CH


2


OC


2


H


5















811























—C


9


H


19















812























—C


5


H


11















813























—OCH


3















814












































815























—C


2


H


5















816























—C


3


H


7















817























—OC


5


H


11















818























—C


4


H


9















819












































820












































821























—C


3


H


7















822























—OC


3


H


7















823












































824























—CH


2


OC


3


H


7















825























—CH


3















826






























—C


3


H


7















827






























—C


2


H


5















828






























—OCH


3















829



















































830



















































831






























—C


3


H


7















832






























—OC


3


H


7















833



















































834






























—C


3


H


6


OC


2


H


5















835






























—CH


3















836























—C


3


H


7















837























—OC


3


H


7















838























—C


2


H


5















839












































840












































841























—C


10


H


21















842























—C


4


H


9















843























—OC


2


H


5















844












































845























—C


2


H


5















846























—C


3


H


7















847























—OC


6


H


13















848























—C


2


H


5















849












































850












































851






























—C


3


H


7















852






























—OC


4


H


9















853



















































854






























—C


3


H


6


OCH


3















855



















































856























—C


3


H


7















857























—C


2


H


5















858























—OC


3


H


7















859












































860












































861























—C


3


H


7















862























—OC


7


H


15















863












































864























—C


2


H


4


OC


2


H


5















865























—CH


3















866






































—C


3


H


7















867






































—OC


3


H


7















868






































—C


2


H


5















869



























































870



























































871






































—C


3


H


7















872






































—C


5


H


11















873






































—OC


2


H


5















874






































—C


3


H


7















875






































—OC


2


H


5















876



























































877






































—C


2


H


5















878






































—C


3


H


7















879






































—OCH


3















880



























































881






































—CH


3















882






































—C


3


H


7















883






































—C


2


H


4


OC


2


H


5















884



























































885






































—C


6


H


13















886






































—CH


3















887






































—OCH


3















888



























































889






































—C


3


H


7















890






































—C


2


H


5















891






































—OC


2


H


5















892



























































893






































—C


3


H


7















894






































—C


3


H


7















895






































—CH


3















896






































—OC


2


H


5















897






































—C


3


H


7















898






































—OCH


3















899



























































900






































—C


8


H


17















901








—C


3


H


7








902








—C


5


H


11








903








—OC


4


H


9















904























—C


5


H


11















905























—C


3


H


7















906












































907























—C


3


H


7















908























—C


5


H


11















909












































910























—C


2


H


5















911























—C


3


H


7















912























—OC


5


H


11















913























—C


3


H


7















914























—C


5


H


11















915























—OCH


3















916








—C


3


H


7








917








—C


4


H


9








918








—OC


6


H


13















919























—C


5


H


11















920























—OC


3


H


7















921























—CH


3















922























—C


3


H


7















923























—OC


3


H


7















924























—CH


3















925























—C


2


H


5















926























—OC


3


H


7















927























—C


6


H


13















928























—C


3


H


7















929























—OC


5


H


11















930












































931






























—CH


3















932






























—OC


2


H


5















933



















































934






























—C


3


H


7















935























—C


3


H


7















936























—OC


4


H


9















937












































938























—C


3


H


7















939






























—C


2


H


5















940






























—CH


3















941






























—OC


3


H


7















942























—C


3


H


7















943























—OC


2


H


5















944












































945























—C


8


H


17















946






























—CH


3















947






























—OC


2


H


5















948



















































949






























—C


3


H


7















950






























—C


4


H


9















951






























—OC


2


H


5















952



















































953






























—C


3


H


7















954













































—C


2


H


5















955













































—C


2


H


5















956













































—OC


4


H


9















957






































—C


3


H


7















958






































—OC


2


H


5















959



























































960






































—C


6


H


11















961








—≡






962








—≡—













963























—≡—













964





























965












































966





























967



























































968












































969





























970





























971





















—≡—





































972




—≡—







































973





























974




—≡—
















—≡—





































975





























976






































—F













977






































—Cl













978






































—OCF


3















979






































—CF


3















980






































—OCHF


2















981






































—OCH


2


CF


3















982






































—F













983






































—OCHF


2















984






































—F













985






































—OCF


3















986






































—F













987






































—Cl













988






































—F













989






































—OCHF


2















990






































—OCF


3















991






































—F














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.












TABLE 1









Method for Description of Compounds Using Symbols






R—(SiH


3


—Y1—)A1—Z1— · · · · · · —Zn—An—X(—Y2)


























1) Left Terminal Group R—, SiH


3


—Y1—




Symbol











C


n


H


2n+1







n—







C


n


H


2n+1


O—




nO—







C


n


H


2n+1


OC


m


H


2m+1







nOm—







CH


2


═CH—




V—







CH


2


═CHC


n


H


2n







Vn—







C


n


H


2n+1


CH═CHC


m


H


2m







nVm—







C


n


H


2n+1


CH═CHC


m


H


2m


CH═CHC


k


H


2k







nVmVk—







CF


2


═CH—




VFF—







CF


2


═CHC


n


H


2n







VFFn—







SiH


3


C


n


H


2n







Sin—











2) Ring Structure —An—




Symbol























B



























B(F)



























B(F, F)



























H



























Ch



























G



























Py



























B(2F, 3F)



























B(2CN, 3CN)











3) Bonding Group —Zn—




Symbol











—C


2


H


4







2







—C


4


H


8







4







—COO—




E







—C≡C—




T







—CH═CH—




V







—CF


2


O—




CF2O







—OCF


2







OCF2











4) Right Terminal Group —X, —Y2




Symbol











—F




—F







—Cl




—CL







—CN




—C







—CF


3






—CF3







—OCF


3






—OCF3







—OCF


2


H




—OCF2H







—C


n


H


2n+1






—n







—OC


n


H


2n+1






—On







—COOCH


3






—EMe







—C


n


H


2n


CH═CH


2






—nV







—C


m


H


2m


CH═CHC


n


H


2n+1






—mVn







—CH═CF


2






—VFF







—C


n


H


2n


CH═CF


2






—nVFF







—C≡C—CN




—TC











5) Examples of Description

















Example 1  3-H2B(F, F)B(F)—F






































Example 2  Si1-HH-5






































Example 3  Si2-HB(F, F)—C






























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





















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)















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




Example 6





















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





















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





















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





















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




3.0%







3-HR-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





















Si2-HB (F, F)-C (No. 459)




12.0% 







2-BEB (F)-C




6.0%







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





















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





















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





















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





















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





















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





















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





















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





















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





















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






















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






















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






















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)













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




Example 23






















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






















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-101





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






















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-1O1





4.0%







5-HBBH-1O1





4.0%













NI = 83.7 (° C.)











η = 38.0 (mPa.s)











Δn = 0.118











Δε = 11.1











Vth = 1.58 (V)













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




Example 26






















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 = 22.0 (mPa.s)











Δn = 0.094











Δε = 8.8











Vth = 1.65 (V)













Example 27






















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






















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






















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






















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






















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






















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






















Si4-HHB (2F, 3F) -O2




(No. 693)




3.0%







Si1-HH-5




(No. 742)




5.0%







Si2-HH-2V




(No. 738)




5.0%







S-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






















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






















S i 2-HHB (F) -OCF3




(No. 36)




7.0%







S i 4-HHB (F) -OCF3




(No. 38)




7.0%







S i 3-HB (F) EB-OCF3




(No. 224)




10.0% 







S i 3-HB (F, F) B (F) -F




(No. 189)




7.0%







S i 3-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)







Δ


n


= 0.092







Δ


ε


= 12.3







Vth = 1.16 (V)















Example 36






















S i 2-HB (F, F) -C




(No. 459)




4.0%







S i 3-HB (F) EB-OCF3




(No. 224)




5.0%







S i 4-HHB (F, F) -OCF2H




(No. 45)




6.0%







S i 2-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)







Δ


n


= 0.069







Δ


ε


= 6.7







Vth = 1.41 (V)















Example 37






















S i 2-HB (F) B (F, F) -F




(No. 193)




10.0%







S i 3-HB (F) B (F, F) -F




(No. 194)




10.0%







S i 4-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)







Δ


n


= 0.148







Δ


ε


= 11.3







Vth = 1.66 (V)















Example 38






















S i 2-HHB (F, F) -OCF2H




(No. 41)




6.0%







S i 2-HB (F) EB-OCF3




(No. 211)




8.0%







S i 2-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)







Δ


n


= 0.083







Δ


ε


= 9.0







Vth = 1.38 (V)















Example 39






















S i 2-HHB (F) -OCF3




(No. 36)




5.0%







S i 2-HB (F, F) B (F) -F




(No. 188)




5.0%







S i 2-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-101





7.0%







NI = 76.7 (° C.)







η = 29.8 (mPa · s)







Δ


n


= 0.114







Δ


ε


= 12.8







Vth = 1.36 (V)















Example 40






















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




(No. 678)




 7.0%







S i 4-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)







Δ


n


= 0.089















Example 41






















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




(No. 678)




12.0%







S i 4-HB (2F, 3F) -O2




(No. 676)




11.0%







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




(No. 691)




14.0%







S i 4-HHB (2F, 3F) -O2




(No. 693)




15.0%







S i 2-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.)







Δ


n


= 0.080







Δ


ε


= −4.0















Example 42






















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




(No. 678)




10.0%







S i 4-HB (2F, 3F) -O2




(No. 676)




10.0%







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




(No. 691)




12.0%







S i 4-HHB (2F, 3F) -O2




(No. 693)




13.0%







S i 2-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.)







Δ


n


= 0.077







Δ


ε


= −3.3















Example 43






















S i 2-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.)







Δ


n


= 0.190







Δ


ε


= −1.9















Example 44






















S i 2-HB (F, F) B (F) -F




(No. 188)




3.0%







S i 2-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-02





7.0%







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





7.0%







NI = 75.4 (° C.)







η = 24.2 (mPa · s)







Δ


n


= 0.155















Example 45






















S i 4-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)







Δ


n


= 0.076







Δ


ε


= −3.5















Example 46






















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




(No. 678)




12.0%







S i 4-HB (2F, 3F) -O2




(No. 676)




12.0%







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




(No. 692)




12.0%







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




(No. 694)




12.0%.







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




(No. 691)




13.0%







S i 4-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)







Δ


n


= 0.090







Δ


ε


= −3.4















Example 47






















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




(No. 678)




12.0%







S i 4-HB (2F, 3F) -O2




(No. 676)




12.0%







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




(No. 692)




12.0%







S i 2-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)







Δ


n


= 0.087







Δ


ε


= −3.7















Example 48






















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




(No. 678)




3.0%







S i 4-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 (2CN, 3CN) -O5





4.0%







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





3.0%







5-HEB (2CN, 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)







Δ


n


= 0.080







Δ


ε


= −5.4







Vth = 1.60 (V)















EFFECTS OF THE INVENTION




The compounds of the present invention, that is, the di- to tetracyclic compounds having SiH


3


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): wherein Y1 is alkylene having 1 to 10 carbon, in which any —CH2— in the 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 —O—, —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.
  • 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 —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—.
  • 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 —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—.
  • 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 —O—, 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; Y1 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. A liquid crystal composition 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: 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.
  • 10. A liquid crystal composition 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: 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 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.
  • 11. A liquid crystal composition 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: 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.
  • 12. A liquid crystal composition 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) 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: 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, 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.
  • 13. A liquid crystal composition 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) as the second component, and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) as the third component: 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 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, 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.
  • 14. A liquid crystal composition 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) as the second component and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) as the third component: 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, 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.
  • 15. A liquid crystal composition 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) as the second component, at least one compound selected from the group of the compounds represented by formulas (5) and (6) as the third component, and at least one compound selected from the group of the compounds represented by formulas (10), (11) and (12) as a fourth component: 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, 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 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, 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)—, —CH═CH—, or a single bond.
  • 16. A liquid crystal composition comprising the liquid crystal composition defined in claim 8 and further comprising at least one optically active compound.
  • 17. A liquid crystal display comprising the liquid crystal composition defined in claim 8.
  • 18. A liquid crystal display comprising the liquid crystal composition defined in claim 9.
  • 19. A liquid crystal display comprising the liquid crystal composition defined in claim 10.
  • 20. A liquid crystal display comprising the liquid crystal composition defined in claim 11.
  • 21. A liquid crystal display comprising the liquid crystal composition defined in claim 12.
  • 22. A liquid crystal display comprising the liquid crystal composition defined in claim 13.
  • 23. A liquid crystal display comprising the liquid crystal composition defined in claim 14.
  • 24. A liquid crystal display comprising the liquid crystal composition defined in claim 15.
Priority Claims (1)
Number Date Country Kind
2000-057164 Mar 2001 JP
US Referenced Citations (1)
Number Name Date Kind
5229481 Tilley Jul 1993 A